English
Tiếng Việt
(en)The polymerizable composition prevents precipitation and the like of crystals and has high storage stability. A polymer compound is added to the polymerizable composition. In a case where a film-shaped polymer obtained by polymerizing the polymerizable composition is prepared, a tilt angle formed with an air interface is small, and glances of reflected light when a circularly polarizing plate is obtained by combining the polymer with a polarizing plate are removed. In addition, there is provided a polymer obtained by polymerizing the polymerizable composition, and an optically anisotropic body using the polymer. The polymerizable composition includes a reverse dispersible compound represented by General Formula (I), and a compound represented by General Formula (II).
1.ApplicationNumber: US-201615543760-A
1.PublishNumber: US-2018037817-A1
2.Date Publish: 20180208
3.Inventor: KUWANA YASUHIRO
HORIGUCHI MASAHIRO
ISHII TORU
NOSE SAYAKA
KOISO AKIHIRO
4.Inventor Harmonized: KUWANA YASUHIRO(JP)
HORIGUCHI MASAHIRO(JP)
ISHII TORU(JP)
NOSE SAYAKA(JP)
KOISO AKIHIRO(JP)
5.Country: US
6.Claims:
(en)The polymerizable composition prevents precipitation and the like of crystals and has high storage stability. A polymer compound is added to the polymerizable composition. In a case where a film-shaped polymer obtained by polymerizing the polymerizable composition is prepared, a tilt angle formed with an air interface is small, and glances of reflected light when a circularly polarizing plate is obtained by combining the polymer with a polarizing plate are removed. In addition, there is provided a polymer obtained by polymerizing the polymerizable composition, and an optically anisotropic body using the polymer. The polymerizable composition includes a reverse dispersible compound represented by General Formula (I), and a compound represented by General Formula (II).
7.Description:
(en)TECHNICAL FIELD
The present invention relates to a polymerizable composition including a compound having a polymerizable group, a polymerizable liquid crystal composition, and an optically anisotropic body using the polymerizable liquid crystal composition.
BACKGROUND ART
A compound including a polymerizable group (polymerizable compound) is used in various optical materials. For example, it is possible to prepare a polymer having even alignment by arranging a polymerizable composition including the polymerizable compound in a liquid crystal state and causing polymerization. Such a polymer can be used in a polarizing plate or a retardation plate necessary for a display. In many cases, a polymerizable composition including two or more kinds of polymerizable compounds is used, in order to satisfy optical characteristics, a rate of polymerization, solubility, a melting point, a glass transition temperature, transparency of a polymer, mechanical strength, surface hardness, heat resistance, and light resistance required. At this time, it is necessary that the polymerizable compound to be used imparts excellent physical properties to the polymerizable composition without negatively affecting other characteristics.
In order to improve a viewing angle of a liquid crystal display, it is necessary that wavelength dispersibility of birefringence of a retardation film is decreased or reversed. Preferred examples of the polymerizable compound to be used for this object include a polymerizable compound which hardly causes occurrence of precipitation of crystals and has high storage stability in a case where the polymerizable compound is added to a polymerizable composition. In addition, with respect to a film-shaped polymer prepared by polymerizing the polymerizable composition containing the polymerizable compound, it is preferable that haze is slight, evenness of film thickness is high, unevenness of alignment hardly occurs, surface hardness is high, and adhesiveness is high. Further, it is preferable that a alignment angle with an air interface is small (a tilt angle is small), because phase difference characteristics of a composition can be exhibited to the maximum degree and angle dependency is also easily adjusted. Meanwhile, by controlling the tilt angle, it is also possible to improve viewing angle characteristics of a display. In a case where a retardation film is used for on-board equipment or mobile equipment, high durability with respect to ultraviolet light is required. Accordingly, in a case where the film-shaped polymer is irradiated with ultraviolet light, it is preferable that discoloration or peeling from a base material hardly occurs and alignment defects hardly occur.
In addition, as an antireflective film of an organic EL element, the use of a circularly polarizing plate prepared by combining the polymer and a polarizing plate with each other has also been investigated. In this case, it is necessary that quantity of reflected light is reduced or glances of the reflected light are removed (set to have an achromatic color) even when the reflected light slightly exists.
CITATION LIST
Patent Literature
[PTL 1] JP-A-2007-328053
SUMMARY OF INVENTION
Technical Problem
An object of the present invention is to provide a polymerizable composition having high storage stability in which precipitation of crystals or the like is prevented in a case where the polymerizable composition is added to a polymerizable composition, with respect to a film-shaped polymer obtained by polymerizing the polymerizable composition, a tilt angle formed with an air interface is small or controlled to be a suitable value, and with respect to a circularly polarizing plate prepared in combination with a polarizing plate, glances of reflected light are reduced. In addition, another object of the present invention is to provide a polymer obtained by polymerizing the polymerizable composition and an optically anisotropic body using the polymer.
Solution to Problem
As a result of intensive studies to solve the problems described above, the inventors have reached the development of a compound represented by General Formula (I). That is, according to the aspect of the present invention, there is provided a polymerizable composition including: (a) a reverse dispersible compound represented by General Formula (I):
(in the formula, R 1 , R 2 , R 3 , and R 4 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 80 carbon atoms, the group may have a substituent, one or more of arbitrary carbon atoms may be substituted with a hetero atom, W 1 and W 2 each independently represent a single bond or a group including a conjugated system including 2 to 100π electrons, M 1 and M 2 each independently represent a group including a mesogenic group, n1 and n2 each independently represent 0 or 1, provided that when n1 or n2 is 0, the corresponding group is a hydrogen atom, n3 represents an integer of 1 to 1,000, W 1 , W 2 , M 1 , and M 2 may each independently include a substituent L, L represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, or L may represent a group represented by P L —(S L —X L ) kL — where P L represents a polymerizable group, S L represents a spacer group or a single bond, in a case where a plurality of S L is present, these may be the same as each other or different from each other, X L represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of X L is present, these may be the same as each other or different from each other (provided that P L —(S L —X L ) kL — does not include a —O—O— bond), in a case where a plurality of L is present in the compound, these may be the same as each other or different from each other, and kL represents an integer of 0 to 10, and M 1 -W 1 , W 1 -M 2 , and/or M 2 -W 2 may each independently form a conjugated system),
(b) a compound represented by General Formula (II):
(in the formula, P 21 represents a polymerizable functional group, S 21 represents an alkylene group having 0 to 18 carbon atoms (hydrogen atoms in the alkylene group may be substituted with one or more halogen atoms or CN, one CH 2 group or two or more of (—CH 2 —)'s that are not adjacent to each other present in this group may be each mutually independently substituted with —O—, —COO—, —OCO—, or —OCO—O—), X 21 represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond (provided that P 21 —S 21 and S 21 —X 21 do not include a —O—O—, —O—NH—, or —O—S— group), q 1 represents 0 or 1, MG represents a mesogenic group, and R 21 represents a hydrogen atom, a halogen atom, a cyano group, or a linear or a branched alkyl group having 1 to 12 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, or a General Formula (II-a):
[Chem. 3]
—(X 22 —S 22 ) q2 —P 23 (II-a)
(in the formula, P 23 represents a reactive functional group, S 22 represents a component which is the same as that defined in the description regarding S 21 , X 22 represents a component which is the same as that defined in the description regarding X 21 (provided that P 23 —S 22 and S 22 —X 22 do not include a —O—O—, —O—NH—, or —O—S— group), and q 2 represents 0 or 1),
(c) an initiator, if necessary, and
(d) a solvent, if necessary,
a polymerizable composition including the compounds, a resin, a resin additive, oil, a filter, an adhesive, a pressure-sensitive adhesive, fat, ink, a medicine, cosmetics, a detergent, a building material, a packaging material, a liquid crystal material, an organic EL material, an organic semiconductor material, an electronic material, a display element, an electronic device, communication equipment, an automobile part, an aircraft part, a machine part, an agricultural chemical, and a food each using the compounds, products using these, a polymerizable liquid crystal composition, a polymer obtained by polymerizing the polymerizable liquid crystal composition, and an optically anisotropic body using the polymer.
Advantageous Effects of Invention
The polymerizable composition including the compounds having a specific structure of the present invention has high storage stability and is useful as a constituent member of a polymerizable composition. In addition, the optically anisotropic body using the polymerizable liquid crystal composition including the compounds of the present invention is useful for an optical material such as a retardation film, because a degree of unevenness is small, a tilt angle formed with an air interface is small or controlled to be a suitable value, glances of reflected light are reduced with respect to a circularly polarizing plate prepared in combination with a polarizing plate.
DESCRIPTION OF EMBODIMENTS
The present invention provides a polymerizable composition formed of a reverse dispersible compound represent by General Formula (I) and a compound represented by General Formula (II), a resin, a resin additive, oil, a filter, an adhesive, a pressure-sensitive adhesive, fat, ink, a medicine, cosmetics, a detergent, a building material, a packaging material, a liquid crystal material, an organic EL material, an organic semiconductor material, an electronic material, a display element, an electronic device, communication equipment, an automobile part, an aircraft part, a machine part, an agricultural chemical, and a food using the composition, products using these, a polymerizable liquid crystal composition, a polymer obtained by polymerizing the polymerizable liquid crystal composition, and an optically anisotropic body using the polymer.
In a graph in which a horizontal axis indicates a wavelength γ of light incident to a retardation film and a vertical axis indicates a birefringence Δn, in a case where the birefringence Δn decreases, as the wavelength γ decreases, the film is generally called as a film showing “reverse wavelength dispersibility” or “reverse dispersibility” by persons skilled in the art. In the present invention, a compound configuring a retardation film showing reverse dispersibility is referred to as a reverse dispersible compound.
<<General Formula (I)>>
In the present invention, a reverse dispersible compound represented by General Formula (I) is included as an essential component.
<<R 1 , R 2 , R 3 , and R 4 >>
In General Formula (I), R 1 , R 2 , R 3 , and R 4 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 80 carbon atoms, the group may have a substituent, and one or more of arbitrary carbon atoms may be substituted with a hetero atom. In addition, R 1 , R 2 , R 3 , and R 4 preferably each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, the group may have a substituent, and one or more of arbitrary carbon atoms may be substituted with a hetero atom. More specifically, R 1 , R 2 , R 3 , and R 4 each independently represent a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a cyano group, a nitro group, an isocyano group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —C═C—, or —C≡C— (one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom), or are preferably a group including a polymerizable group.
In General Formula (I), regarding R 1 , R 2 , R 3 , and R 4 , R 1 being present and at least one of R 2 , R 3 , and R 4 being present are preferably groups including a polymerizable group.
The group including a polymerizable group is preferably a group represented by General Formula (I-R).
(In the formula, P 1 represents a polymerizable group, S 1 represents a spacer group or a single bond, in a case where a plurality of S 1 is present, these may be the same as each other or different from each other, X 1 represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of X 1 is present in the compound, these may be the same as each other or different from each other (provided that P 1 —(S 1 —X 1 ) k — does not include a —O—O— bond), and k represents an integer of 0 to 10.)
In General Formula (I-R), P 1 represents a polymerizable group and preferably represents a group selected from Formula (P-1) to Formula (P-20).
These polymerizable groups are polymerized by radical polymerization, radical addition polymerization, cation polymerization, and anion polymerization. Particularly, in a case of performing ultraviolet ray polymerization as a polymerization method, Formula (P-1), Formula (P-2), Formula (P-3), Formula (P-4), Formula (P-5), Formula (P-7), Formula (P-11), Formula (P-13), Formula (P-15), or Formula (P-18) is preferable, Formula (P-1), Formula (P-2), Formula (P-7), Formula (P-11), or Formula (P-13) is more preferable, Formula (P-1), Formula (P-2), or Formula (P-3) is even more preferable, and Formula (P-1) or Formula (P-2) is particularly preferable.
In General Formula (I-R), S 1 represents a spacer group or a single bond, and in a case where a plurality of S 1 is present, these may be the same as each other or different from each other. In addition, S 1 , as a spacer group, preferably represents an alkylene group having 1 to 20 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, —OCO—, —OCO—O—, —CO—NH—, —NH—CO—, —CH═CH—, or —C≡C—. From viewpoints of availability of raw materials and ease of synthesis, in a case where a plurality of S 1 is present, these may be the same as each other or different from each other, S 1 's more preferably each independently represent an alkylene group having 1 to 10 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, or —OCO—, or a single bond, even more preferably each independently represent an alkylene group having 1 to 10 carbon atoms or a single bond. In a case where a plurality of S 1 is present, these may be the same as each other or different from each other, and S 1 's particularly preferably each independently represent an alkylene group having 1 to 8 carbon atoms.
In General Formula (I-R), X 1 represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, and in a case where a plurality of X 1 is present, these may be the same as each other or different from each other (provided that P 1 —(S 1 —X 1 ) k — does not include a —O—O— bond). From viewpoints of availability of raw materials and ease of synthesis, in a case where a plurality of X 1 is present, these may be the same as each other or different from each other, X 1 's more preferably each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond, even more preferably each independently represent —O—, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond. In a case where a plurality of X 1 is present, these may be the same as each other or different from each other, and X 1 's particularly preferably each independently represent —O—, —COO—, —OCO—, or a single bond.
In General Formula (I-R), k represents an integer of 0 to 10, preferably represents an integer of 0 to 5, more preferably represents an integer of 0 to 2, and particularly preferably represents 1.
In a case where R 1 , R 2 , R 3 , and R 4 of General Formula (I) represent a group other than the group including a polymerizable group, R 1 , R 2 , R 3 , and R 4 preferably represent a group selected from R 5 (in the formula, R 5 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom).
From viewpoints of liquid crystal properties, reverse dispersibility, ease of synthesis, and storage stability, the group represented by R 5 more preferably represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, —OCO—, —O—CO—O—, —CO—NH—, or —NH—CO— and one or more of arbitrary hydrogen atoms may be substituted with a fluorine atom, even more preferably represents a hydrogen atom, a fluorine atom, a chlorine atom, or a linear alkyl group having 1 to 10 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, —OCO—, or —O—CO—O— and one or more of arbitrary hydrogen atoms may be substituted with a fluorine atom, still more preferably represents a linear alkyl group having 1 to 10 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, and particularly preferably represents a linear alkyl group having 1 to 5 carbon atoms.
<<Substituent L>>
A compound represented by General Formula (I) may be unsubstituted or substituted with a substituent L. The substituent L represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or a branched alkyl group having 1 to 20 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, or L may represent a group represented by P L —(S L —X L ) kL — where P L represents a polymerizable group, S L represents a spacer group or a single bond, in a case where a plurality of SL is present, these may be the same as each other or different from each other, X L represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of X L is present, these may be the same as each other or different from each other (provided that P L —(S L —X L ) kL — does not include a —O—O— bond), kL represents an integer of 0 to 10, kL is preferably 1, and in a case where a plurality of L is present in the compound, these may be the same as each other or different from each other. In addition, from viewpoints of availability of raw materials and ease of synthesis, in a case where a plurality of the substituents L are present, these may be the same as each other or different from each other, and the substituent L preferably represents a fluorine atom, a chlorine atom, a nitro group, a cyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, or —OCO— and one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom. In a case where a plurality of the substituents L are present, these may be the same as each other or different from each other, and the substituent L more preferably represents a fluorine atom, a chlorine atom, a nitro group, a cyano group, or a linear alkyl group having 1 to 12 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—. In a case where a plurality of the substituents L are present, these may be the same as each other or different from each other, and the substituent L particularly preferably represents a fluorine atom, a cyano group, a methyl group, or a methoxy group.
<<W 1 and W 2 >
In General Formula (I), W 1 and W 2 each independently represent a group including a single bond or a conjugated system including 2 to 100π electrons. From viewpoints of availability of raw materials and ease of synthesis, W 1 and W 2 are preferably groups including a single bond or a carbon group or a hydrocarbon group including 2 to 80π electrons, in which one or more of arbitrary carbon atoms may be substituted with a hetero atom, and a single bond or an aromatic and/or nonaromatic hydrocarbon ring having 5 to 80 carbon atoms, which is not substituted or may be substituted with one or more of substituents L and in which one or more of arbitrary carbon atoms may be substituted with a hetero atom.
In General Formula (I), W 1 more preferably represents a group represented by General Formula (I-W1) and W 2 more preferably represents a group represented by General Formula (I-W2).
In the formula, V 1 , V 2 , V 3 , and V 4 each independently represent a single bond or a divalent linking group, B 1 , B 2 , and B 3 each independently represent a single bond or an aromatic and/or nonaromatic hydrocarbon ring having 5 to 80 carbon atoms which may be substituted, one or more of arbitrary carbon atoms of the carbon ring or the hydrocarbon ring may be substituted with a hetero atom, these groups may be unsubstituted or substituted with one or more of substituents L. In a case where B 3 represents a single bond, a hydrogen atom or a group represented by the substituent L is bonded thereto, and n4 and n5 are integers of 0 to 10.)
In the formula, V 1 , V 2 , V 3 , and V 4 preferably each independently represent a group selected from Formula (V-1) to Formula (V-15).
In the formulae, Y 1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, and in a case where a plurality of Y 1 is present, these may be the same as each other or different from each other. Alternatively, Y 1 may represent a group represented by P Y —(S Y —X Y ) j —, P Y represents a polymerizable group and preferably represents a group selected from Formula (P-1) to Formula (P-20), and the polymerizable groups are polymerized by radical polymerization, radical addition polymerization, cation polymerization, and anion polymerization. Particularly, in a case of performing ultraviolet ray polymerization as a polymerization method, Formula (P-1), Formula (P-2), Formula (P-3), Formula (P-4), Formula (P-5), Formula (P-7), Formula (P-11), Formula (P-13), Formula (P-15), or Formula (P-18) is preferable, Formula (P-1), Formula (P-2), Formula (P-7), Formula (P-11), or Formula (P-13) is more preferable, Formula (P-1), Formula (P-2), or Formula (P-3) is even more preferable, and Formula (P-1) or Formula (P-2) is particularly preferable. S Y represents a spacer group or a single bond, and in a case where a plurality of S Y is present, these may be the same as each other or different from each other. From viewpoints of liquid crystal properties, availability of raw materials, and ease of synthesis, in a case where a plurality of S Y is present, these may be the same as each other or different from each other, and S Y 's preferably each independently represent an alkylene group having 1 to 20 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF═S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, or —C≡C—. In a case where a plurality of S Y is present, these may be the same as each other or different from each other, and S Y 's more preferably each independently represent a linear alkylene group having 1 to 20 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, —OCO—, or —OCO—O—. In a case where a plurality of S Y is present, these may be the same as each other or different from each other, and S Y 's even more preferably each independently represent a linear alkylene group having 1 to 12 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—. From viewpoints of liquid crystal properties and solubility in a solvent, S Y particularly preferably represents a linear alkylene group having 1 to 12 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—. X Y represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, and in a case where a plurality of X Y is present, these may be the same as each other or different from each other (provided that P Y —(S Y —X Y ) j — does not include a —O—O— bond). From viewpoints of availability of raw materials and ease of synthesis, in a case where a plurality of X Y is present, these may be the same as each other or different from each other, X Y 's preferably each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond, more preferably each independently represent —O—, —COO—, OCO—, or a single bond, and particularly preferably represents a single bond. j represents an integer of 0 to 10, and preferably represents an integer of 1 to 3, from viewpoints of liquid crystal properties and availability of raw materials. j particularly preferably represents 1, from a viewpoint of hardening shrinkage in a case where a film is obtained.
In Formula (V-1) to Formula (V-15), in a case where the group represented by P Y —(S Y —X Y ) j — is bonded to a N atom, a group directly bonded to the N atom is preferably —CH 2 —, from a viewpoint of ease of synthesis.
In Formula (V-1) to Formula (V-15), from viewpoints of a phase difference, temporal stability of reverse wavelength dispersibility, and peeling in a case of irradiation with ultraviolet light for a long period of time, the group represented by P Y —(S Y —X Y ) j — preferably represents a group selected from Formula (PY-1), Formula (PY-2), or Formula (PY-3).
(In the formula, ja represents an integer of 2 to 20 and jb represents an integer of 1 to 6.) In the Formula (PY-1), from a viewpoint of liquid crystal properties, ja more preferably represents an integer of 2 to 12 and particularly preferably represents an integer of 2 to 8. In Formula (PY-2) and Formula (PY-3), from a viewpoint of liquid crystal properties, jb more preferably represents an integer of 1 to 3 and particularly preferably represents 1 or 2.
In Formula (V-1) to Formula (V-15), in a case where Y 1 represents a group other than the group represented by P Y —(S Y —X Y ) j —, Y 1 represents a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, and in a case where a plurality of Y 1 is present, these preferably represent groups which may be the same as each other or different from each other. In this case, from viewpoints of liquid crystal properties, availability of raw materials, and ease of synthesis, in a case where a plurality of Y 1 is present, these may be the same as each other or different from each other, and Y 1 more preferably represents a linear or branched alkyl group having 1 to 20 carbon atoms, in which one or more of arbitrary hydrogen atoms in the group may be substituted with a fluorine atom and one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —CO—, —COO—, —OCO—, —O—CO—O—, —CH═CH—, —CF═CF—, or —C≡C—. In a case where a plurality of Y 1 is present, these may be the same as each other or different from each other, and Y 1 even more preferably represents a linear alkyl group having 1 to 20 carbon atoms, in which one or more of arbitrary hydrogen atoms in the group may be substituted with a fluorine atom and one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—. In a case where a plurality of Y 1 is present, these may be the same as each other or different from each other, and Y 1 particularly preferably represents a linear alkyl group having 1 to 10 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—. In addition, from viewpoints of solubility in various solvents and adhesiveness to various base materials (or aligned films), Y 1 is preferably a group selected from a group represented by H 3 C—(O— (CH 2 ) j1 ) j2 — (in the formula, j1 represents an integer of 2 to 10, j2 represents an integer of 1 to 10, j1 is preferably an integer of 2 to 6, j2 is preferably an integer of 1 to 4, j1 is more preferably 2 or 3, j2 is more preferably an integer of 1 to 3, j1 is particularly preferably 2, and j2 is particularly preferably 2 or 3), a single bond, a double bond, —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 1 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, and —CH 2 —OCO—, provided that at least one of M 1 -V 1 , V 1 —B 1 , B 1 —V 2 , V 2 -M 2 , M 2 -V 3 , V 3 —B 2 , B 2 —V 4 , and V 4 —B 3 present in Formula (I-W1) and Formula (I-W2) forms a conjugated system.
From viewpoints of reverse dispersibility, availability of raw materials, and ease of synthesis, V 1 , V 2 , V 3 , and V 4 are more preferably each independently a group selected from the groups represented by Formula (V-1) to (V-15), a single bond, a double bond, —O—, —S—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, and —CH 2 —OCO—, even more preferably each independently a group selected from the groups represented by Formula (V-1) to (V-15), a single bond, a double bond, —S—, —CH 2 —, —COO—, —OCO—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, and —CH 2 CH 2 —, still more preferably each independently a group selected from the groups represented by Formula (V-1) to (V-15), a single bond, a double bond, —CH 2 —, —COO—, —OCO—, and —CH 2 CH 2 —, and particularly preferably each independently a group selected from the groups represented by Formula (V-1) to (V-15), a single bond, and a double bond, provided that at least one of M 1 -V 1 , V 1 —B 1 , B 1 —V 2 , V 2 -M 2 , M 2 -V 3 , V 3 —B 2 , B 1 —V 4 , and V 4 —B 3 present in Formula (I-W1) and Formula (I-W2) forms a conjugated system.
From viewpoints of availability of raw materials and ease of synthesis, in a case where Y 1 is bonded to a carbon atom, Y 1 preferably represents a hydrogen atom, a fluorine atom, a chlorine atom, a nitro group, a cyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, or —OCO— and one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, more preferably represents a hydrogen atom, a fluorine atom, a chlorine atom, a nitro group, a cyano group, or a linear alkyl group having 1 to 12 carbon atoms, even more preferably represents a hydrogen atom, a fluorine atom, a cyano group, or a linear alkyl group having 1 to 8 carbon atoms, and particularly preferably represents a hydrogen atom. In addition, in a case where Y 1 is bonded to a nitrogen atom, Y 1 preferably represents a hydrogen atom or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, OR—OCO— and one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, more preferably represents a hydrogen atom or a linear or branched alkyl group having 1 to 20 carbon atoms, even more preferably represents a hydrogen atom or a linear or branched alkyl group having 1 to 8 carbon atoms, and particularly preferably represents a hydrogen atom.
In the formulae, B 1 being present and B 2 and B 3 being present preferably each independently represent Formula (B-1) to Formula (B-21) or a single bond.
(in the formulae, in a ring structure, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. Here, the expression that a bonding site may be at an arbitrary position, means that, since B 1 is a divalent group, two bonding sites are provided at arbitrary positions, for example (hereinafter, in the present invention, the expression that a bonding site may be at an arbitrary position, indicates the same meaning). In addition, these groups may be unsubstituted or substituted with one or more of substituents L, and in a case where B 3 represents a single bond, these groups are bonded to a hydrogen atom or a group represented by the substituent L).
From viewpoints of availability of raw materials, ease of synthesis, and reverse dispersibility, B 1 , B 2 , and B 3 preferably each independently represent a group selected from Formula (B-3), Formula (B-4), Formula (B-5), Formula (B-6), Formula (B-7), Formula (B-8), Formula (B-10), Formula (B-11), Formula (B-12), Formula (B-13), Formula (B-17), Formula (B-18), Formula (B-19), Formula (B-20), Formula (B-21), or a single bond.
A group represented by Formula (B-3) preferably represents a group selected from Formula (B-3-1) to Formula (B-3-7),
(in the formulae, in a ring structure, a bonding site may be at an arbitrary position, and R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. In addition, these groups may be unsubstituted or substituted with one or more of substituents L), and more preferably represents a group selected from Formula (B-3-2), Formula (B-3-4), Formula (B-3-5), Formula (B-3-6), and Formula (B-3-7).
A group represented by Formula (B-4) preferably represents a group selected from Formula (B-4-1) to Formula (B-4-8),
(in the formulae, in a ring structure, a bonding site may be at an arbitrary position. In addition, these groups may be unsubstituted or substituted with one or more of substituents L), and more preferably represents a group represented by Formula (B-4-1).
A group represented by Formula (B-5) preferably represents a group selected from Formula (B-5-1) to Formula (B-5-6).
(In the formulae, in a ring structure, a bonding site may be at an arbitrary position, and R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.)
A group represented by Formula (B-6) preferably represents a group selected from Formula (B-6-1) to Formula (B-6-9).
(In the formulae, in a ring structure, a bonding site may be at an arbitrary position, and R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.)
A group represented by Formula (B-7) preferably represents a group selected from Formula (B-7-1) to Formula (B-7-12),
(in the formulae, in a ring structure, a bonding site may be at an arbitrary position, and R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. In addition, these groups may be unsubstituted or substituted with one or more of substituents L), and more preferably represents a group selected from Formula (B-7-8), Formula (B-7-9), Formula (B-7-10), Formula (B-7-11), and Formula (B-7-12), and even more preferably represents a group represented by Formula (B-7-11)
A group represented by Formula (B-8) preferably represents a group selected from Formula (B-8-1) to Formula (B-8-8),
(in the formulae, in a ring structure, a bonding site may be at an arbitrary position, and R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. In addition, these groups may be unsubstituted or substituted with one or more of substituents L), and more preferably represents a group selected from Formula (B-8-2), Formula (B-8-3), Formula (B-8-4), Formula (B-8-6), Formula (B-8-7), and Formula (B-8-8).
A group represented by Formula (B-10) preferably represents a group selected from Formula (B-10-1) to Formula (B-10-19).
(In the formulae, in a ring structure, a bonding site may be at an arbitrary position, and R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.)
A group represented by Formula (B-11) preferably represents a group selected from Formula (B-11-1) to Formula (B-11-7),
(in the formulae, in a ring structure, a bonding site may be at an arbitrary position, and R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. In addition, these groups may be unsubstituted or substituted with one or more of substituents L), and more preferably represents a group selected from Formula (B-11-1), Formula (B-11-2), and Formula (B-11-7).
A group represented by Formula (B-12) preferably represents a group selected from Formula (B-12-1) to Formula (B-12-4),
(in the formulae, in a ring structure, a bonding site may be at an arbitrary position, and R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. In addition, these groups may be unsubstituted or substituted with one or more of substituents L), and more preferably represents a group selected from Formula (B-12-1) and Formula (B-12-4).
A group represented by Formula (B-13) preferably represents a group selected from Formula (B-13-1) to Formula (B-13-10).
(In the formulae, in a ring structure, a bonding site may be at an arbitrary position, and R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.)
A group represented by Formula (B-17) preferably represents a group selected from Formula (B-17-1) to Formula (B-17-18).
(In the formulae, in a ring structure, a bonding site may be at an arbitrary position, and R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.)
A group represented by Formula (B-18) preferably represents a group selected from Formula (B-18-1) to Formula (B-18-4).
(In the formulae, in a ring structure, a bonding site may be at an arbitrary position, and R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.)
A group represented by Formula (B-19) preferably represents a group selected from Formula (B-19-1) to Formula (B-19-16).
(In the formulae, in a ring structure, a bonding site may be at an arbitrary position, and R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.)
A group represented by Formula (B-20) preferably represents a group selected from Formula (B-20-1) to Formula (B-20-12).
(In the formulae, in a ring structure, a bonding site may be at an arbitrary position, and R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.)
A group represented by Formula (B-21) preferably represents a group selected from Formula (B-21-1) to Formula (B-21-13).
(In the formulae, in a ring structure, a bonding site may be at an arbitrary position, and R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.)
<<M 1 and M 2 >>
In General Formula (I), M 1 and M 2 each independently represent a group including a mesogenic group.
More specifically, M 1 preferably represents a group represented by Formula (I-M1) and M 2 preferably represents a group represented by Formula (I-M2).
(In the formula, A 1 , A 2 , A 3 , and A 4 each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, these groups may be unsubstituted or substituted with one or more of substituents L, and, in a case where a plurality of each of A 1 , A 2 , A 3 , and A 4 is present, these may be the same as each other or different from each other. Z 1 , Z 2 , Z 3 , and Z 4 each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of each of Z 1 , Z 2 , Z 3 , and Z 4 is present, these may be the same as each other or different from each other. T 1 represents a trivalent group which may be substituted, in a case where n2 is 0, T 2 represents a trivalent group which may be substituted, in a case where n2 is 1, T 2 represents a tetravalent group which may be substituted, and m1, m2, m3, and m4 each independently represent an integer of 0 to 5.)
From viewpoints of availability of raw materials and ease of synthesis, A 1 , A 2 , A 3 , and A 4 preferably represent a 1,4-phenylene group, a 1,4-cyclohexylene group, or a naphthalene-2,6-diyl group which are not substituted or may be substituted with one or more substituent L, more preferably each independently represent a group selected from Formula (A-1) to Formula (A-11),
even more preferably each independently represent a group selected from Formula (A-1) to Formula (A-8), and particularly preferably each independently represent a group selected from Formula (A-1) to Formula (A-4).
From viewpoints of liquid crystal properties of the compound, availability of raw materials, and ease of synthesis, Z 1 , Z 2 , Z 3 , and Z 4 preferably each independently represent a single bond, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —CF═CF—, —C≡C—, or a single bond, more preferably each independently represent —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —C≡C—, or a single bond, even more preferably each independently represent —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond, and particularly preferably each independently represent —COO—, —OCO—, or a single bond.
m1, m2, m3, and m4 each independently represent an integer of 0 to 5, and from viewpoints of liquid crystal properties, ease of synthesis, and storage stability, m1, m2, m3, and m4 preferably each independently represent an integer of 1 to 4, more preferably each independently represent an integer of 1 to 3, and particularly preferably each independently represent 1 or 2. m1+m2 and m3+m4 preferably each independently represent an integer of 1 to 4 and particularly preferably each independently represent 2, 3, or 4.
In Formula (I-M1) and Formula (I-M2), T 1 and T 2 are preferably each independently a group selected from Formula (T-1) to Formula (T-22).
(In the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L, and k1 represents an integer of 1 to 20.)
<<n1, n2, and n3>>
n1 and n2 each independently represent 0 or 1. In a case where n1 is 0, a group linked to W 1 which will be described later represents a hydrogen atom, and in a case where n2 is 0, a group linked to M 2 which will be described later represents a hydrogen atom.
n3 represents an integer of 1 to 1,000, preferably represents an integer of 1 to 10, more preferably represents an integer of 1 to 5, even more preferably represents an integer of 1 to 3, and particularly preferably represents 1 or 2.
n1, n2, and n3 each represent the numbers described above, a case where A: <n1 and n2 represent 0 and n3 represents 1>, B: <n1 represents 1, n2 represents 0, and n3 represents 1>, C: <n1 represents 0, and n2 and n3 represent 1>, or D: <n1 and n2 represent 0 and n3 represents 2 to 1,000> is particularly preferable, because excellent reverse dispersibility is exhibited. Hereinafter, each group will be described in the aspects A: to D: which are particularly preferred aspects.
Compound in Which <<n1 and n2 Represent 0 and n3 Represents 1>>
<W 1 -A11>
In the compound in which <n1 and n2 represent 0 and n3 represents 1>, in a case of significantly considering surface hardness and appearance after ultraviolet light irradiation, when a film-shaped polymer is prepared, in General Formula (I), W 1 is preferably a group represented by Formula (I-W11).
(In the formula, V 1 and V 2 being present each independently represent a single bond or a divalent linking group, B 1 being present and B 11 each independently a group selected from Formula (B-1) to Formula (B-21),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and a single bond, and n41 represents an integer of 0 to 5.)
V 1 and V 2 are preferably each independently the groups represented by Formula (V-1) to Formula (V-15) shown in the section <<W 1 and W 2 >> (in the formulae, in a case of including Y 1 , Y 1 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis described in the section <<W 1 and W 2 >>), a single bond, a double bond, —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, more preferably a group selected from Formula (V-5), Formula (V-6), Formula (V-8), Formula (V-9), Formula (V-10), a single bond, and a double bond, and particularly preferably a single bond.
B 1 and B 11 are preferably each independently a group selected from Formula (B-3), Formula (B-4), Formula (B-8), Formula (B-13), Formula (B-16), and a single bond, and more preferably each independently a group selected from Formula (B-3), Formula (B-4), Formula (B-8), and a single bond. More specifically, B 1 and B 11 are specifically preferably each independently a group selected from Formula (B-3-1), Formula (B-3-2), Formula (B-3-5), Formula (B-3-7), Formula (B-4-1), Formula (B-8-4), Formula (B-8-7), Formula (B-13-7), Formula (B-13-8) shown in the section <<W 1 and W 1 >>, and a single bond, and specifically preferably each independently a group selected from Formula (B-3-7), Formula (B-4-1), and Formula (B-8-4).
n41 more preferably represents 0, 1, or 2, even more preferably represents 0 or 1, and still more preferably represents 1.
<W 1 -A12>
In the compound in which <n1 and n2 represent 0 and n3 represents 1>, in a case of significantly considering storage stability of a polymerizable composition, unevenness of alignment when a film-shaped polymer is prepared, and alignment defects after ultraviolet light irradiation, in General Formula (I), W 1 is preferably a group represented by Formula (I-W12).
(In the formula, V 1 and V 2 being present each independently represent a single bond or a divalent linking group, V 21 represents —NR 0 —, —CR 0 ═, ═CR 0 —, —N═, or ═N— (in the formulae, R 0 's each independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms), B 1 being present and B 11 each independently a group selected from Formula (B-1) to Formula (B-21),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and a single bond, and n41 represents an integer of 0 to 5.) V 21 more preferably represents a group selected from —NR 0 —, —N═, and ═N— (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms) and even more preferably represents —NH—.
V 1 and V 2 being present are more preferably each independently a group represented by Formula (V-1) to Formula (V-15) (in the formulae, in a case of including Y 1 , Y 1 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis described in the section <<W 1 and W 2 >>), a single bond, a double bond, —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, and —CH 2 —OCO—, even more preferably each independently Formula (V-1), Formula (V-2), Formula (V-5), Formula (V-6), Formula (V-8), Formula (V-9), a single bond, —S—, or —CH 2 CH 2 —, and still more preferably each independently Formula (V-5) or a single bond.
B 1 and B 1 are preferably each independently a group selected from Formula (B-3), Formula (B-4), Formula (B-6), Formula (B-7), Formula (B-8), Formula (B-10), Formula (B-11), Formula (B-21), and a single bond, and more preferably each independently a group selected from Formula (B-3), Formula (B-4), Formula (B-8), and Formula (B-21). More specifically, B 1 and B 11 are preferably a group selected from Formula (B-3-2), Formula (B-3-5), Formula (B-3-7), Formula (B-4-1), Formula (B-4-2), Formula (B-4-3), Formula (B-4-4), Formula (B-4-5), Formula (B-6-7), Formula (B-7-8), Formula (B-7-11), Formula (B-7-12), Formula (B-8-3), Formula (B-8-4), Formula (B-10-11), Formula (B-10-16), Formula (B-11-6), and Formula (B-21-12) shown in the section <<W 1 and W 2 >>, and more preferably a group selected from Formula (B-3-7), Formula (B-4-1), Formula (B-4-2), Formula (B-4-3), Formula (B-8-4), and Formula (B-21-12).
n41 more preferably represents 0, 1, or 2 and even more preferably represents 0 or 1.
<W 1 -A13>
In the compound in which <n1 and n2 represent 0 and n3 represents 1>, in a case of significantly considering evenness of film thickness and adhesiveness, when a film-shaped polymer is prepared, in General Formula (I), W 1 is preferably a group represented by Formula (I-W13).
(In the formula, V 1 and V 2 being present each independently represent a single bond or a divalent linking group, V 21 represents —CR 0 ═CR 0 —, —C≡C—, —CR 0 ═N—, —N═CR 0 —, —NR 0 —CR 0 ═, ═CR 0 —NR 0 —, —NR 0 —N═, ═N—NR 0 —, —N═N—, or ═N—N═ (in the formulae, R 0 's each independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms), B 1 being present and B 11 each independently a group selected from Formula (B-1) to Formula (B-21),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and a single bond, and n41 represents an integer of 0 to 5.) V 21 more preferably represents a group selected from —CR 0 ═CR 0 —, —C≡C—, —CR 0 ═N—, —N═CR 0 —, —NR 0 —CR 0 ═, ═CR 0 —NR 0 —, —N═N—, or ═N—N═ (in the formulae, R 0 's each independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms), even more preferably represents a group selected from —CH═CH—, —CH═N—, —N═CH—, and —N═N—, and still more preferably represents a group selected from —CH═CH—, —CH═N—, and —N═CH—. V 1 and V 2 are more preferably each independently a group represented by Formula (V-1) to Formula (V-15) (in the formulae, in a case of including Y 1 , Y 1 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis described in the section <<W 1 and W 2 >>), a single bond, a double bond, —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, and —CH 2 —OCO—, even more preferably each independently Formula (V-1), Formula (V-2), Formula (V-3), Formula (V-4), Formula (V-5), Formula (V-10), —CH 2 CH 2 —, or a single bond, and still more preferably each independently Formula (V-1), Formula (V-2), Formula (V-3), Formula (V-4), or a single bond. B 1 and B 11 are preferably each independently a group selected from Formula (B-3), Formula (B-4), Formula (B-5), Formula (B-6), Formula (B-7), Formula (B-8), Formula (B-10), Formula (B-1), Formula (B-12), Formula (B-13), Formula (B-17), Formula (B-18), and a single bond, and more preferably each independently a group selected from Formula (B-3), Formula (B-4), Formula (B-7), Formula (B-8), Formula (B-10), Formula (B-12), Formula (B-13), and a single bond. More specifically, B 1 and B 11 are preferably a group selected from Formula (B-3-2), Formula (B-3-5), Formula (B-4-1), Formula (B-7-11), Formula (B-8-7), Formula (B-10-11), Formula (B-12-3), Formula (B-12-4), Formula (B-13-6), and a single bond, more preferably a group selected from Formula (B-3-2), Formula (B-3-5), Formula (B-4-1), Formula (B-7-11), Formula (B-8-7), Formula (B-12-4) shown in the section <<W 1 and W 2 >>, and a single bond, and even more preferably a group selected from Formula (B-3-2), Formula (B-4-1), Formula (B-8-7), Formula (B-12-4), and a single bond.
n41 more preferably represents 0, 1, or 2, even more preferably represents 0 or 1, and still more preferably represents 1.
<W 1 -A14>
In the compound in which <n1 and n2 represent 0 and n3 represents 1>, in a case of significantly considering storage stability when the compound is added to a polymerizable composition, a haze value when a film-shaped polymer is prepared, and alignment defects after ultraviolet light irradiation, in General Formula (I), W 1 is preferably a group represented by Formula (I-W14).
(In the formula, V 1 and V 2 being present each independently represent a single bond or a divalent linking group, V 21 represents —CR 0 ═CR 0 —, —C≡C—, —CR 0 ═N—, —N═CR 0 —, —NR 0 —CR 0 ═, ═CR 0 —NR 0 —, —NR 0 —N═, ═N—NR 0 —, —N═N—, or ═N—N═, V 22 represents —NR 0 —, —CR 0 ═, ═CR 0 —, —N═, or ═N— (in the formulae, R 0 's each independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms), B 1 being present and B 11 each independently a group selected from Formula (B-1) to Formula (B-21),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and a single bond, and n41 represents an integer of 0 to 5.) V 21 more preferably represents a group selected from —CR 0 ═N—, —N═CR 0 —, —NR 0 —CR 0 ═, ═CR 0 —NR 0 —, —NR 0 —N═, ═N—NR 0 —, and ═N—N═ (in the formulae, R 0 each independently represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms), and even more preferably represents a group selected from —CH═N—, —N═CH—, —NH—CH═, ═CH—NH—, —NH—N═, ═N—NH—, and ═N—N═. V 22 more preferably represents a group selected from —NR 0 —, —N═, and ═N— (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms) and even more preferably represents a group selected from —NH—, —N═, and ═N—. V 1 and V 2 being present are more preferably each independently a group represented by Formula (V-1) to Formula (V-15) (in the formulae, in a case of including Y 1 , Y 1 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis described in the section <<W 1 and W 2 >>), a single bond, a double bond, —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, and —CH 2 —OCO—, even more preferably each independently Formula (V-5), Formula (V-6), Formula (V-8), Formula (V-9), a single bond, or —CH 2 CH 2 —, and still more preferably each independently a single bond. B 1 being present and B 11 are preferably each independently a group selected from Formula (B-3), Formula (B-4), Formula (B-7), Formula (B-8), Formula (B-10), Formula (B-11), Formula (B-12), and a single bond, and more preferably each independently a group selected from Formula (B-4), Formula (B-7), Formula (B-8), and a single bond. More specifically, B 1 being present and B 11 are preferably a group selected from Formula (B-3-1), Formula (B-3-2), Formula (B-3-5), Formula (B-3-7), Formula (B-4-1), Formula (B-4-3), Formula (B-4-6), Formula (B-7-11), Formula (B-8-4), Formula (B-8-7), Formula (B-10-11), Formula (B-11-1), Formula (B-12-4) shown in the section <<W 1 and W 1 >>, and a single bond, and more preferably a group selected from Formula (B-4-1), Formula (B-7-11), Formula (B-8-7), and a single bond.
n41 more preferably represents 0, 1, or 2, even more preferably represents 0 or 1, and still more preferably represents 0.
<W 1 -A15>
In the compound in which <n1 and n2 represent 0 and n3 represents 1>, in a case of significantly considering a haze value and evenness of film thickness, when a film-shaped polymer is prepared, in General Formula (I), W 1 is preferably a group represented by Formula (I-W18).
(In the formula, V 1 and V 2 being present each independently represent a single bond or a divalent linking group, V 21 , V 22 , V 23 , and V 24 represent —CR 0 ═CR 0 —, —C≡C—, —CR 0 ═N—, —N═CR 0 —, —NR 0 —CR 0 ═, ═CR 0 —NR 0 —, —NR 0 —N═, ═N—NR 0 —, —N═N—, ═N—N═, —NR 0 —, —CR 0 ═, ═CR 0 —, —N═, or ═N— (in the formulae, R 0 's each independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms), B 1 and B 1 being present each independently a group selected from Formula (B-1) to Formula (B-21),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and a single bond, and n41 represents an integer of 0 to 5.) V 21 , V 22 , V 23 , and V 24 preferably represent —CR 0 ═CR 0 —, —C≡C—, —CR 0 ═N—, —N═CR 0 —, —NR 0 —CR 0 ═, ═CR 0 —NR 0 —, —NR 0 —N═, ═N—NR 0 —, —NR 0 —, —CR 0 ═, ═CR 0 —, —N═, or ═N— (in the formulae, R 0 each independently represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms), more preferably represent —CR 0 ═CR 0 —, —C≡C—, —CR 0 ═N—, —N═CR 0 —, —NR 0 —N═, ═N—NR 0 —, —NR 0 —, —CR 0 ═, or ═CR 0 — (in the formulae, R 0 each independently represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms), even more preferably represent —CR 0 ═N— or —N═CR 0 — (in the formulae, R 0 each independently represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms), and still more preferably —CH═N— or —N═CH—. V 1 and V 2 being present are more preferably each independently a group represented by Formula (V-1) to Formula (V-15) (in the formulae, in a case of including Y 1 , Y 1 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis described in the section <<W 1 and W 2 >>), a single bond, a double bond, —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, and —CH 2 —OCO—, even more preferably each independently Formula (V-6), a single bond, or —CH 2 CH 2 —, and still more preferably each independently Formula (V-6) or a single bond. B 1 being present and B 11 are preferably each independently a group selected from Formula (B-3), Formula (B-4), Formula (B-7), Formula (B-8), Formula (B-10), Formula (B-11), Formula (B-12), or a single bond, and more preferably each independently a group selected from Formula (B-4), Formula (B-8), Formula (B-12), or a single bond. More specifically, B 1 being present and B 11 are preferably a group selected from Formula (B-3-2), Formula (B-3-5), Formula (B-4-1), Formula (B-7-11), Formula (B-8-7), Formula (B-10-11), Formula (B-11-1), Formula (B-12-4) shown in the section <<W 1 and W 2 >>, and a single bond, more preferably a group selected from Formula (B-4-1), Formula (B-8-7), Formula (B-12-4), and a single bond, and even more preferably a group selected from Formula (B-4-1) and a single bond.
n41 more preferably represents 0, 1, or 2, even more preferably represents 0 or 1, and still more preferably represents 1.
<M 2 -A1>
In the compound in which <n1 and n2 represent 0 and n3 represents 1>, in a case of significantly considering storage stability when the compound is added to a polymerizable composition, a haze value, evenness of film thickness, unevenness of alignment, and surface hardness, when a film-shaped polymer is prepared, in General Formula (I), M 2 represents Formula (I-M21),
(in the formula, A 31 being present and A 41 being present each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, these groups may be unsubstituted or substituted with one or more of substituents L, and, in a case where a plurality of each of A 31 and A 41 is present, these may be the same as each other or different from each other. Z 31 being present and Z 41 being present each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of each of Z 31 and Z 41 is present, these may be the same as each other or different from each other. m31 and m41 each independently represent an integer of 0 to 5.), and T 21 represents a group selected from Formula (T2-1) to Formula (T2-10).
These groups may be unsubstituted or substituted with one or more of substituents L, and m31+m41 is preferably a group representing 1 to 6.
From viewpoints of availability of raw materials and ease of synthesis, A 31 and A 41 more preferably each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, or a naphthalene-2,6-diyl group which are not substituted or may be substituted with one or more substituent L, more preferably each independently represent a group selected from Formula (A-A1-1) to Formula (A-A1-11),
even more preferably each independently represent a group selected from Formula (A-A1-1) to Formula (A-A1-8), and particularly preferably each independently represent a group selected from Formula (A-A1-1) to Formula (A-A1-4).
From viewpoints of liquid crystal properties of the compound, availability of raw materials, and ease of synthesis, Z 31 and Z 41 preferably each independently represent a single bond, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —CF═CF—, —C≡C—, or a single bond, more preferably each independently represent —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —C≡C—, or a single bond, even more preferably each independently represent —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond, and particularly preferably each independently represent —COO—, —OCO—, or a single bond.
From viewpoints of liquid crystal properties, ease of synthesis, and storage stability, m31 and m41 preferably each independently represent an integer of 1 to 4, more preferably each independently represent an integer of 1 to 3, and particularly preferably each independently represent 1 or 2. m31+m41 preferably each independently represents an integer of 1 to 4 and particularly preferably each independently represent 2, 3, or 4.
T 21 is more preferably a group represented by Formula (T2-1) to Formula (T2-6) and even more preferably a group represented by Formula (T2-1) to Formula (T2-2).
In addition, in a case where M 2 is a group represented by Formula (I-M21), a group selected from <W 1 -A11> to <W 1 -A15> is preferably used and <W 1 -A11>, <W 1 -A12>, or <W 1 -A14> is more preferably used as W 1 .
<M 2 -A2>
In the compound in which <n1 and n2 represent 0 and n3 represents 1>, in a case of significantly considering appearance and alignment defects after ultraviolet light irradiation, when a film-shaped polymer is prepared, in General Formula (I), M 2 represents Formula (I-M22),
(in the formula, A 32 being present and A 42 being present each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, these groups may be unsubstituted or substituted with one or more of substituents L, and, in a case where a plurality of each of A 32 and A 42 is present, these may be the same as each other or different from each other. Z 32 being present and Z 42 being present each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of each of Z 32 and Z 42 is present, these may be the same as each other or different from each other. T 22 represents a trivalent group which may be substituted, and m32 and m42 each independently represent an integer of 0 to 5.), in Formula (I-M22), T 22 represents a group selected from Formula (T2-11) to Formula (T2-27)
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), Formula (T2-28) to Formula (T2-31),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), Formula (T2-32),
(in the formula, a bonding site may be at an arbitrary position, at least one —CH 2 — is each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and Formula (T2-33) or Formula (T2-34),
(in the formulae, a bonding site may be at an arbitrary position, at least one —CH═ is each independently substituted with —N═. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and m32+m42 is preferably a group representing an integer of 1 to 6.
In addition, M 2 represents Formula (I-M222),
(in the formula, A 322 and A 42 each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, these groups may be unsubstituted or substituted with one or more of substituents L, and, in a case where a plurality of each of A 322 and A 422 is present, these may be the same as each other or different from each other. Z 322 and Z 422 each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of each of Z 322 and Z 422 is present, these may be the same as each other or different from each other. T 222 represents a trivalent group which may be substituted), in Formula (I-M222), T 222 represents a group selected from Formula (T2-35) to Formula (T2-41)
(in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), and m322 and m422 preferably each independently represent 1 or 2.
From viewpoints of availability of raw materials and ease of synthesis, A 322 and A 422 preferably represent a 1,4-phenylene group, a 1,4-cyclohexylene group, or a naphthalene-2,6-diyl group which are not substituted or may be substituted with one or more substituent L, more preferably each independently represent a group selected from Formula (A-A2-1) to Formula (A-A2-11),
even more preferably each independently represent a group selected from Formula (A-A2-1) to Formula (A-A2-8), and particularly preferably each independently represent a group selected from Formula (A-A2-1) to Formula (A-A2-4).
From viewpoints of liquid crystal properties of the compound, availability of raw materials, and ease of synthesis, Z 322 and Z 422 preferably each independently represent a single bond, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH—CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH 2 —, —CF═CF—, —C≡C—, or a single bond, more preferably each independently represent —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —C≡C—, or a single bond, even more preferably each independently represent —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond, and particularly preferably each independently represent —COO—, —OCO—, or a single bond.
T 222 is more preferably a group represented by Formula (T2-36), Formula (T2-38), Formula (T2-39), Formula (T2-40), or Formula (T2-41).
<W 1 -A2>
In the compound in which <n1 and n2 represent 0 and n3 represents 1>, in a case of significantly considering appearance and alignment defects after ultraviolet light irradiation, when a film-shaped polymer is prepared, in General Formula (I), W 1 preferably represents a group selected from Formula (I-W19).
(In the formula, V 1 and V 2 each independently represent a single bond or a divalent linking group, B 1 each independently represents a group selected from Formula (B-1) to Formula (B-21),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and a single bond, and n4 represents an integer of 0 to 5.)
V 1 and V 2 are preferably each independently the groups represented by Formula (V-1) to Formula (V-15) shown in the section <(<W 1 and W 2 >> (in the formulae, in a case of including Y 1 , Y 1 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis described in the section <<W 1 and W 2 >>), a single bond, a double bond, —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, and —CH 2 —OCO—, more preferably a group selected from Formula (V-1), Formula (V-2), Formula (V-5), Formula (V-6), Formula (V-7), Formula (V-8), Formula (V-9), Formula (V-12), Formula (V-13), —COO—, and —OCO—, and even more preferably a group selected from Formula (V-5), Formula (V-6), Formula (V-7), Formula (V-8), Formula (V-9), Formula (V-12), Formula (V-13), —COO—, and —OCO—.
B 1 is preferably each independently a group selected from Formula (B-4), Formula (B-8), Formula (B-11), Formula (B-12), and a single bond. More specifically, B 1 is preferably a group selected from Formula (B-4-1), Formula (B-8-7), Formula (B-11-1), Formula (B-12-4) shown in the section <<W 1 and W 2 >>, and a single bond, and more preferably a group selected from Formula (B-4-1), Formula (B-8-7), Formula (B-12-4), and a single bond.
n4 represents preferably 0 to 8 and more preferably represents 0 to 6.
In addition, in a case where T 222 represents a group selected from Formula (T2-35) or Formula (T2-36), in Formula (I-W19), B 1 represents a single bond, n4 represents 1 to 6, and V 1 and V 2 preferably represent a group other than a single bond.
<M 2 -A3>
In the compound in which <n1 and n2 represent 0 and n3 represents 1>, in a case of significantly considering storage stability when the compound is added to a polymerizable composition, evenness of film thickness and alignment defects after ultraviolet light irradiation, when a film-shaped polymer is prepared, in General Formula (I), M represents Formula (I-M23),
(in the formula, A 33 being present and A 43 being present each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, these groups may be unsubstituted or substituted with one or more of substituents L, and, in a case where a plurality of each of A 33 and A 43 is present, these may be the same as each other or different from each other. Z 33 being present and Z 43 being present each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of each of Z 33 and Z 43 is present, these may be the same as each other or different from each other. T 23 represents a trivalent group which may be substituted, and m33 and m43 each independently represent an integer of 0 to 5.), in Formula (I-M23), T 23 represents an acyclic group having 1 to 80 carbon atoms which may be substituted, arbitrary carbon atoms of the acyclic group may be substituted with hetero atoms, and m33+m43 is preferably a group representing an integer of 1 to 6.
In addition, M 2 represents Formula (I-M232),
(in the formula, A 33 being present and A 432 being present each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, these groups may be unsubstituted or substituted with one or more of substituents L, and, in a case where a plurality of each of A 332 and A 432 is present, these may be the same as each other or different from each other. Z 332 being present and Z 43 being present each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of each of Z 332 and Z 432 is present, these may be the same as each other or different from each other. T 232 represents a trivalent group which may be substituted, and m332 and m432 each independently represent an integer of 0 to 5), in Formula (I-M232), T 232 represents a group represented by Formula (T-22),
(in the formula, a bonding site may be at an arbitrary position, arbitrary —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formula, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L, and k1 represents an integer of 1 to 20.), and m332+m432 more preferably represents an integer of 1 to 6.
From viewpoints of availability of raw materials and ease of synthesis, A 332 and A 432 more preferably represent a 1,4-phenylene group, a 1,4-cyclohexylene group, or a naphthalene-2,6-diyl group which are not substituted or may be substituted with one or more substituent L, more preferably each independently represent a group selected from Formula (A-A2-1) to Formula (A-A2-11),
even more preferably each independently represent a group selected from Formula (A-A3-1) to Formula (A-A3-8), and particularly preferably each independently represent a group selected from Formula (A-A3-1) to Formula (A-A3-4).
From viewpoints of liquid crystal properties of the compound, availability of raw materials, and ease of synthesis, Z 332 and Z 432 preferably each independently represent a single bond, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —CF═CF—, —C≡C—, or a single bond, more preferably each independently represent —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —C≡C—, or a single bond, even more preferably each independently represent —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond, and particularly preferably each independently represent —COO—, —OCO—, or a single bond.
From viewpoints of liquid crystal properties, ease of synthesis, and storage stability, m332 and m432 preferably each independently represent an integer of 1 to 4, more preferably each independently represent an integer of 1 to 3, and particularly preferably each independently represent 1 or 2. m31+m41 preferably each independently represent an integer of 1 to 4 and particularly preferably each independently represent 2, 3, or 4.
T 232 preferably represents a group selected from Formula (T-22-1) or Formula (T-22-2),
(in the formulae, arbitrary —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formula, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L, and k131 to k134 represent an integer of 0 to 20), and more preferably represent Formula (T-22-1). It is particularly preferable that k131 and k132 in Formula (T-22-1) represent 1.
<W 1 -A3>
In the compound in which <n1 and n2 represent 0 and n3 represents 1>, in a case of significantly considering storage stability when the compound is added to a polymerizable composition, evenness of film thickness and alignment defects after ultraviolet light irradiation, when a film-shaped polymer is prepared, in General Formula (I), W 1 represents Formula (I-W20).
(In the formula, V 1 and V 2 being present each independently represent a single bond or a divalent linking group, B's being present each independently a group selected from Formula (B-1) to Formula (B-21),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and a single bond, and n4 represents an integer of 0 to 5.)
V 1 and V 2 are preferably each independently the groups represented by Formula (V-1) to Formula (V-15) shown in the section <<W 1 and W 2 >> (in the formulae, in a case of including Y 1 , Y 1 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis described in the section <<W 1 and W 2 >>), a single bond, a double bond, —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, and —CH 2 —OCO—, more preferably a group selected from Formula (V-5), Formula (V-6), Formula (V-8), Formula (V-9), Formula (V-10), and a single bond, and even more preferably a group selected from Formula (V-5), Formula (V-6), Formula (V-8), and Formula (V-9). In addition, from a viewpoint of ease of synthesis, a group directly bonded to T 232 among the groups represented by V 2 is preferably a group other than the group represented by Formula (V-6).
B 1 is preferably each independently a group selected from Formula (B-4), Formula (B-8), Formula (B-11), and a single bond. More specifically, B 1 is preferably a group selected from Formula (B-4-1), Formula (B-8-7), Formula (B-11-1), shown in the section <<W 1 and W 2 >>, and a single bond, and more preferably a group selected from Formula (B-4-1), and a single bond.
<R 3 and R 4 >
In the compound in which <n1 and n2 represent 0 and n3 represents 1>, M 2 and W 1 described above are preferably suitably selected and the following groups are preferably used as R 3 and R 4 .
R 3 represents a group represented by Formula (I-R).
(In the formula, P 1 represents a polymerizable group, S 1 represents a spacer group or a single bond, in a case where a plurality of S 1 is present, these may be the same as each other or different from each other, X 1 represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of X 1 is present in the compound, these may be the same as each other or different from each other (provided that P 1 —(S 1 —X 1 ) k — does not include a —O—O— bond), and k represents an integer of 0 to 10.) R 4 preferably represents a group selected from the group represented by Formula (I-R) and R 5 (in the formula, R 5 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom). Both R 3 and R 4 are particularly preferably the group represented by Formula (I-R), and in this case, the preferable groups and numerical values shown in the section of <<R 1 , R 2 , R 3 , and R 4 >> are respectively applied to P 1 , S 1 , X 1 , and k.
Compound in Which <<n1 Represents 1, n2 Represents 0, and n3 Represents 1>>
<W 1 —B11>
In the compound in which <n1 represents 1, n2 represents 0, and n3 represents 1>, in a case of significantly considering unevenness of alignment and surface hardness, when a film-shaped polymer is prepared, in General Formula (I), W 1 is preferably a group represented by Formula (I-W15).
(In the formula, Y B represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, and in a case where a plurality of Y B is present, these may be the same as each other or different from each other. Alternatively, Y B may represent a group represented by P—(S—X) j —, P represents a polymerizable group, S represents a spacer group or a single bond, in a case where a plurality of S is present, these may be the same as each other or different from each other, X represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of X is present, these may be the same as each other or different from each other (provided that P—(S—X) j — does not include a —O—O— bond), j represents an integer of 0 to 10, B 11 represents a group selected from Formula (B-1) to Formula (B-21)
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L), or a single bond, n41 represents an integer of 0 to 5.) In addition, Y B more preferably represents a hydrogen atom, a fluorine atom, a chlorine atom, a nitro group, a cyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, even more preferably represents a hydrogen atom or a methyl group, and still more preferably represents a hydrogen atom. B 11 is preferably each independently a group selected from Formula (B-4) and Formula (B-11). More specifically, B 11 is specifically preferably a group selected from Formula (B-4-1) and Formula (B-11-1) shown in the section <<W 1 and W 2 >>. n41 more preferably represents 0, 1, or 2, even more preferably represents 0 or 1, and still more preferably represents 0.
<W 1 —B2>
In the compound in which <n1 represents 1, n2 represents 0, and n3 represents 1>, in a case of significantly considering surface hardness and adhesiveness, when a film-shaped polymer is prepared, in General Formula (I), W 1 is preferably a group represented by Formula (I-W21).
(In the formula, V 1 and V 2 each independently represent a single bond or a divalent linking group, B 1 each independently represents a group selected from Formula (B-1) to Formula (B-21),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and a single bond, and n4 represents an integer of 0 to 5.)
V 1 and V 1 are preferably each independently the groups represented by Formula (V-1) to Formula (V-15) shown in the section <<W 1 and W 2 >> (in the formulae, in a case of including Y 1 , Y 1 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis described in the section <<W 1 and W 2 >>), a single bond, a double bond, —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, and —CH 2 —OCO—, more preferably a group selected from Formula (V-1), Formula (V-2), Formula (V-5), Formula (V-6), Formula (V-7), Formula (V-8), Formula (V-9), a single bond, —COO—, —OCO—, —CO—NH—, —NH—CO—, and —CH 2 CH 2 —, even more preferably a group selected from Formula (V-1), Formula (V-2), Formula (V-5), Formula (V-7), a single bond, —COO—, —OCO—, —CO—NH—, —NH—CO—, and —CH 2 CH 2 —, and still more preferably a group selected from Formula (V-1), Formula (V-2), —COO—, —OCO—, —CO—NH—, —NH—CO—, and —CH 2 CH 2 —.
B 1 is preferably each independently a group selected from Formula (B-4), Formula (B-20), and a single bond. More specifically, B 1 is specifically preferably a group selected from Formula (B-4-1), Formula (B-20-2) shown in the section <<W 1 and W2>>, and a single bond.
<W 1 —B3>
In the compound in which <n1 represents 1, n2 represents 0, and n3 represents 1>, in a case of significantly considering adhesiveness, and appearance after ultraviolet light irradiation, when a film-shaped polymer is prepared, in General Formula (I), W1 is preferably a group represented by Formula (I-W22).
(In the formula, V 2 and V 2 each independently represent a single bond or a divalent linking group, B 1 each independently represents a group selected from Formula (B-1) to Formula (B-21),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and a single bond, and n4 represents an integer of 0 to 5.)
V 1 and V 2 are preferably each independently the groups represented by Formula (V-1) to Formula (V-15) shown in the section <<W 1 and W 2 >> (in the formulae, in a case of including Y 1 , Y 1 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis described in the section <<W 1 and W 2 >>), a single bond, a double bond, —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, and —CH 2 —OCO—, more preferably a group selected from Formula (V-6), Formula (V-7), Formula (V-8), Formula (V-9), Formula (V-10), a single bond, —COO—, —OCO—, —CS—NH—, and —NH—CS—, and even more preferably a group selected from Formula (V-8), Formula (V-9), —COO—, and —OCO—.
B 1 is preferably each independently a group selected from Formula (B-4), Formula (B-11), and a single bond, and more preferably each independently a group selected from Formula (B-4) and a single bond. More specifically, B 1 is preferably a group selected from Formula (B-4-1), Formula (B-11-1) shown in the section <<W 1 and W 2 >>, and a single bond, and more preferably a group selected from Formula (B-4-1) and a single bond.
<M 1 -B and M 2 -B>
In the compound in which <n1 represents 1, n2 represents 0, and n3 represents 1>, unevenness of alignment, surface hardness, or adhesiveness, when a film-shaped polymer is prepared, are excellent due to the structure of the compound. Therefore, in General Formula (I), M 1 represents a group represented by Formula (I-M14) and M 2 represents a group represented by Formula (I-M24).
(In the formula, A 14 , A 24 , A 34 , and A 44 each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, these groups may be unsubstituted or substituted with one or more of substituents L, and, in a case where a plurality of each of A 14 , A 24 , A 34 , and A 44 is present, these may be the same as each other or different from each other. Z 14 , Z 24 , Z 34 , and Z 44 each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of each of Z 14 , Z 24 , Z 34 , and Z 44 is present, these may be the same as each other or different from each other. m14, m24, m34, and m44 each independently represent an integer of 0 to 5.)
In Formula (I-M14) and Formula (I-M24), T 14 and T 24 are preferably each independently a group selected from Formula (T-1) to Formula (T-22).
(In the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L, and k1 represents an integer of 1 to 20.) In addition, T 14 and T 24 preferably each independently represent one group selected from Formula (T-1) to Formula (T-22) and even more preferably each independently represent the same group.
From viewpoints of availability of raw materials and ease of synthesis, A 14 , A 24 , A 34 , and A 44 preferably represent a 1,4-phenylene group, a 1,4-cyclohexylene group, or a naphthalene-2,6-diyl group which are not substituted or may be substituted with one or more substituent L, more preferably each independently represent a group selected from Formula (A-A2-1) to Formula (A-A2-11),
even more preferably each independently represent a group selected from Formula (A-A3-1) to Formula (A-A3-8), and particularly preferably each independently represent a group selected from Formula (A-A3-1) to Formula (A-A3-4).
From viewpoints of liquid crystal properties of the compound, availability of raw materials, and ease of synthesis, Z 14 , Z 24 , Z 34 , and Z 44 preferably each independently represent a single bond, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —CF═CF—, —C≡C—, or a single bond, more preferably each independently represent —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —C≡C—, or a single bond, even more preferably each independently represent —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond, and particularly preferably each independently represent —COO—, —OCO—, or a single bond.
From viewpoints of liquid crystal properties of the compound, ease of synthesis, and storage stability, m14, m24, m34, and m44 preferably each independently represent an integer of 1 to 4, more preferably each independently represent an integer of 1 to 3, and particularly preferably each independently represent 1 or 2. m14+m24 and m34+m44 preferably each independently represent an integer of 1 to 4 and more preferably each independently represent 2, 3, or 4.
<M 1 -B11 and M 2 -B11>
In a case of significantly considering unevenness of alignment and surface hardness, when a film-shaped polymer is prepared, T 14 in Formula (I-M14) preferably represents the component described above and T 24 in Formula (I-M24) preferably represents a group selected from Formula (T2-1) to Formula (T2-10).
These groups may be unsubstituted or substituted with one or more of substituents L.
In addition, T 24 is more preferably a group represented by Formula (T2-1) to Formula (T2-6) and even more preferably a group represented by Formula (T2-1) or Formula (T2-2). Further, T 14 represents a group selected from Formula (T1-1) to Formula (T1-10).
These groups may be unsubstituted or substituted with one or more of substituents L. It is more preferable that T 24 represents a group selected from Formula (T2-1) to Formula (T2-10) and these groups may be unsubstituted or substituted with one or more of substituents L. It is even more preferable that T 14 represents a group selected from Formula (T1-1) to Formula (T1-6) and T 24 represents a group selected from Formula (T2-1) to Formula (T2-6). It is still more preferable that T 14 represents a group selected from Formula (T1-1) or Formula (T1-2) and T 24 represents a group selected from Formula (T2-1) or Formula (T2-2).
<M 1 -B2>
In addition, in a case of significantly considering surface hardness and adhesiveness, when a film-shaped polymer is prepared, T 14 in Formula (I-M14) represents the component shown in the section <M 1 -B and M 2 -B>, and T 24 in Formula (I-M24) represents a group selected from Formula (T2-11) to Formula (T2-27),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L.), Formula (T2-28) to Formula (T2-31),
(in the formulae, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L.), Formula (T2-32),
(in the formula, a bonding site may be at an arbitrary position, at least one —CH 2 — is each independently substituted with —O—, —S—, —NR 0 — (in the formula, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L.), and Formula (T2-33) or Formula (T2-34),
(in the formulae, a bonding site may be at an arbitrary position, and at least one —CH═ is each independently substituted with —N═. In addition, these groups may be unsubstituted or substituted with one or more of L.), and m34+m44 is preferably a group representing an integer of 1 to 6.
Further, T 24 in Formula (I-M24) particularly preferably represents a group selected from Formula (T2-35) to Formula (T2-41).
(In the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.) Further, it is more preferable that T 14 in Formula (I-M14) represents a group selected from Formula (T1-11) to Formula (T1-27),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L.), Formula (T1-28) to Formula (T1-31),
(in the formulae, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L.), Formula (T1-32),
(in the formula, a bonding site may be at an arbitrary position, at least one —CH 2 — is each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L.), and Formula (T1-33) or Formula (T1-34),
(in the formulae, a bonding site may be at an arbitrary position, at least one —CH═ is each independently substituted with —N═. In addition, these groups may be unsubstituted or substituted with one or more of L.), and T 24 in Formula (I-M24) represents a group selected from Formula (T2-11) to Formula (T2-41). Further, it is even more preferable that T 14 in Formula (I-M14) represents a group selected from Formula (T1-35) to Formula (T1-41),
(in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), and T 24 in Formula (I-M24) represents a group selected from Formula (T2-35) to Formula (T2-41). In addition, in a case where T 14 represents a group selected from Formula (T1-40) or Formula (T1-41) and T 24 represents a group selected from Formula (T2-40) or Formula (T2-41), in Formula (I-W21), V 1 and V 2 preferably represent a group other than the group represented by Formula (V-6).
<M 1 -B3>
In addition, in a case of significantly considering adhesiveness, and appearance after ultraviolet light irradiation, when a film-shaped polymer is prepared, it is preferable that T 14 in Formula (I-M14) represents the component described above and T 24 represents an acyclic group having 1 to 80 carbon atoms which may be substituted, and one or more of arbitrary carbon atoms of the acyclic group may be substituted with hetero atoms.
Further, T 24 preferably represents a group represented by Formula (T-22)
(in the formula, a bonding site may be at an arbitrary position, arbitrary —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formula, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L, and k1 represents an integer of 1 to 20.), preferably represents a group selected from Formula (T-22-1) or Formula (T-22-2),
(in the formulae, arbitrary —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formula, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L, and k131 to k134 represent an integer of 0 to 20), and more preferably represents Formula (T-22-1). It is even more preferable that k131 and k132 in Formula (T-22-1) represent 1. In addition, in Formula (T-22-1), k131 represents 0 and k132 represents 1. In a case where k131 represents 1 and k132 represents 0, in Formula (I-W22), a group represented by V 2 directly bonded to T 14 and T 24 preferably represents a group other than Formula (V-6) and a single bond. Further, it is preferable that both T 14 and T 24 represent a group represented by Formula (T-22), it is more preferable that both T 14 and T 24 represent a group represented by Formula (T-22-1) or Formula (T-22-2), and it is even more preferable that both T 14 and T 24 represent Formula (T-22-1).
<R 1 , R 2 , R 3 , and R 4 >
Meanwhile, in the compound in which <n1 represents 1, n2 represents 0, and n3 represents 1>, unevenness of alignment, surface hardness, or adhesiveness, when a film-shaped polymer is prepared, are excellent due to the structure of the compound. Therefore, in General Formula (I), M 1 , M 2 , and W 1 described above are preferably suitably selected and the following groups are preferably used as R 1 to R 4 .
R 4 and R 3 represent a group represented by Formula (I-R).
(In the formula, P represents a polymerizable group, S represents a spacer group or a single bond, in a case where a plurality of S is present, these may be the same as each other or different from each other, X represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of X is present in the compound, these may be the same as each other or different from each other (provided that P—(S—X) k — does not include a —O—O— bond), k represents an integer of 0 to 10.) R 1 and R 4 preferably represent a group selected from the group represented by Formula (I-R) and R 5 (in the formula, R 5 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom).
In addition, in the compound in which <n1 represents 1, n2 represents 0, and n3 represents 1>, in a case of significantly considering unevenness of alignment and surface hardness, when a film-shaped polymer is prepared, in General Formula (I), it is preferable that R 2 and R 3 represent a group represented by Formula (I-R) and R 1 and R 4 represent a group represented by R 5 , and in this case, the preferable groups and numerical values shown in the section of <<R 1 , R 2 , R 3 , and R 4 >> are respectively applied to P, S, X, k, and R 5 .
Further, in the compound in which <n1 represents 1, n2 represents 0, and n3 represents 1>, in a case of significantly considering surface hardness and adhesiveness, when a film-shaped polymer is prepared, or in a case of significantly considering adhesiveness, and appearance after ultraviolet light irradiation, when a film-shaped polymer is prepared, all of R 1 , R 2 , R 3 , and R 4 are particularly preferably a group represented by Formula (I-R), and in this case, the preferable groups and numerical values shown in the section of <<R 1 , R 2 , R 3 , and R 4 >> are respectively applied to P, S, X, and k.
Compound in which <<n1 Represents 0, and n2 and n3 Represent 1>>
<M 2 -C>
In addition, in the compound in which <n1 represents 0, and n2 and n3 represent 1>, evenness of film thickness, surface hardness, and/or alignment defects after ultraviolet light irradiation, when a film-shaped polymer is prepared, are excellent due to the structure of the compound. Therefore, in General Formula (I), M 2 represents Formula (I-M2C).
(In the formula, A 3C being present and A 4C being present each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, these groups may be unsubstituted or substituted with one or more of substituents L, and, in a case where a plurality of each of A 3C and A 4C are present, these may be the same as each other or different from each other. Z 3C and Z 4C each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of each of Z 3C and Z 4C is present, these may be the same as each other or different from each other. m3C and m4C each independently represent an integer of 0 to 5.) In Formula (I-M 2 C), T 2C preferably represents a group selected from Formula (T-1) to Formula (T-22)
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L, and k1 represents an integer of 1 to 20.), and these groups preferably represent groups which may be unsubstituted or substituted with one or more of substituents L.
From viewpoints of availability of raw materials and ease of synthesis, A 3C and A 4C preferably represent a 1,4-phenylene group, a 1,4-cyclohexylene group, or a naphthalene-2,6-diyl group which are not substituted or may be substituted with one or more substituent L, more preferably each independently represent a group selected from Formula (A-C-1) to Formula (A-C-11),
even more preferably each independently represent a group selected from Formula (A-C-1) to Formula (A-C-8), and particularly preferably each independently represent a group selected from Formula (A-C-1) to Formula (A-C-4).
From viewpoints of liquid crystal properties of the compound, availability of raw materials, and ease of synthesis, Z 3 c and Z 4C preferably each independently represent a single bond, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH—CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —CF═CF—, —C≡C—, or a single bond, more preferably each independently represent —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —C≡C—, or a single bond, even more preferably each independently represent —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond, and particularly preferably each independently represent —COO—, —OCO—, or a single bond.
From viewpoints of liquid crystal properties, ease of synthesis, and storage stability, m3C and m4C preferably each independently represent an integer of 1 to 4, more preferably each independently represent an integer of 1 to 3, and particularly preferably each independently represent 1 or 2. m3C+m4C preferably each independently represent an integer of 1 to 4 and more preferably each independently represent 2, 3, or 4.
<M 2 -C11 and M 2 -C12>
In a case of significantly considering evenness of film thickness, when a film-shaped polymer is prepared, T 2C in Formula (I-M2C) represents a group selected from Formula (T2-C-1) to Formula (T2-C-12).
These groups are preferably groups which may be unsubstituted or substituted with one or more of substituents L.
In addition, T 2C is more preferably a group represented by Formula (T2-C-1) to Formula (T2-C-4) and even more preferably a group represented by Formula (T2-C-1) or Formula (T2-C-4).
<M 2 -C2>
In addition, in a case of significantly considering storage stability of a composition, and alignment defects after ultraviolet light irradiation, when a film-shaped polymer is prepared, T 2C in Formula (I-M2C) preferably represents a group selected from Formula (T2-C-13) to Formula (T2-C-42).
(In the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L.) T 2C more preferably represents a group selected from Formula (T2-C-13), Formula (T2-C-22), Formula (T2-C-27), Formula (T2-C-28), Formula (T2-C-29), Formula (T2-C-36), Formula (T2-C-37), Formula (T2-C-38), Formula (T2-C-39), and Formula (T2-C-41), even more preferably represents a group selected from Formula (T2-C-13), Formula (T2-C-27), and Formula (T2-C-29), and still more preferably represents Formula (T2-C-13).
<M 2 -C3>
In addition, in a case of significantly considering surface hardness and alignment defects after ultraviolet light irradiation, when a film-shaped polymer is prepared, it is preferable that T 2C in Formula (I-M2C) represents an acyclic group having 1 to 80 carbon atoms which may be substituted, and one or more of arbitrary carbon atoms of the acyclic group may be substituted with hetero atoms.
Further, T 2C preferably represents a group represented by Formula (T-22)
(in the formula, a bonding site may be at an arbitrary position, arbitrary —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formula, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L, and k1 represents an integer of 1 to 20.), and more preferably represents a group selected from Formula (T-22-3),
(in the formula, arbitrary —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formula, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L, and k141 and k142 represent an integer of 0 to 20). k141 and k42 in Formula (T-22-3) more preferably represent an integer of 1 to 10, k141 and k42 in Formula (T-22-3) even more preferably represent an integer of 1 to 4, and k141 and k42 in Formula (T-22-3) particularly preferably represent 1.
<W 1 -M 2 -W 2 —C1>
In the compound in which <n1 represents 0, and n2 and n3 represent 1>, due to the structure of the compound, evenness of film thickness, when a film-shaped polymer is prepared, is high, surface hardness is high, and/or alignment defects after ultraviolet light irradiation hardly occurs. Therefore, in General Formula (I), the groups shown in the section <M 2 -C11 and M 2 -C12> are preferably used as M 2 , and a group represented by W 1 -M 2 -W 2 (provided that M 2 is linked to R 3 and R 4 at arbitrary positions) preferably represents a group selected from Formula (I-W16-1) or Formula (I-W16-2).
(In the formula, Y C1 and Y C4 each independently represent a group including aromatic and/or nonaromatic carbon ring or heterocyclic ring having 1 to 80 carbon atoms which may be substituted, and one or more of arbitrary carbon atoms of the carbon ring or the heterocyclic ring may be substituted with hetero atoms (provided that oxygen atoms are not directly bonded to each other). Y C2 and Y C3 each independently represent a hydrogen atom or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, Y C2 and Y C3 may represent a group having 5 to 30 carbon atoms including at least one aromatic group, the group may be unsubstituted or substituted with one or more of substituents L. Y C represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, and in a case where a plurality of Y C is present, these may be the same as each other or different from each other. Alternatively, Y C may represent a group represented by P—(S—X) j —, P represents a polymerizable group, S represents a spacer group or a single bond, in a case where a plurality of S is present, these may be the same as each other or different from each other, X represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of X is present, these may be the same as each other or different from each other (provided that P—(S—X) j — does not include a —O—O— bond), j represents an integer of 0 to 10, Y C1 and Y C2 may be integrated to form a ring structure, and Y C3 and Y C4 may be integrated to form a ring structure.)
From viewpoints of liquid crystal properties and ease of synthesis, Y C in Formula (I-W16-1) and Formula (I-W16-2) preferably represents a linear or branched alkyl group having 1 to 12 carbon atoms, in which one or more of arbitrary hydrogen atoms in the group may be substituted with a fluorine atom and one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, or —OCO—, more preferably represents a linear or branched alkyl group having 1 to 12 carbon atoms, in which one or more of arbitrary hydrogen atoms in the group may be substituted with a fluorine atom, and particularly preferably represents a linear alkyl group having 1 to 12 carbon atoms.
Y C1 and Y C4 in Formula (I-W16-1) and Formula (I-W16-2) preferably each independently a group represented by Formula (B-1) to Formula (B-21).
(In the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.) Y C1 and Y C4 more preferably each independently a group selected from Formula (B-8) and Formula (B-12). More specifically, Y C1 and Y C4 are preferably a group selected from Formula (B-8-1) and Formula (B-12-1) shown in the section <<W 1 and W 2 >>.
From viewpoints of availability of raw materials and ease of synthesis, in a case where Y C2 and Y C3 in Formula (I-W16-1) and Formula (I-W16-2) each independently represent a hydrogen atom, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and one or more of arbitrary hydrogen atoms may be substituted with a fluorine atom, Y C2 and Y C3 preferably each independently represent a hydrogen atom, or a linear or branched alkyl group having 1 to 12 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —CO—, —COO—, or —OCO—, and one or more of arbitrary hydrogen atoms may be substituted with a fluorine atom, more preferably each independently represent a hydrogen atom, or a linear or branched alkyl group having 1 to 12 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —CO—, —COO—, or —OCO—, even more preferably each independently represent a hydrogen atom, or a linear alkyl group having 1 to 8 carbon atoms, and still more preferably each independently represent a hydrogen atom. In addition, from viewpoints of availability of raw materials and ease of synthesis, in a case where Y C2 and Y C3 represent a group having 5 to 30 carbon atoms including at least one aromatic group, which may be unsubstituted or substituted with one or more of substituents L, Y C2 and Y C3 are preferably each independently a group represented by Formula (B-1) to Formula (B-21),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), Y C2 and Y C3 are more preferably each independently a group selected from Formula (B-8) and Formula (B-12). More specifically, the group selected from Formula (B-8-1) and Formula (B-12-1) shown in the section <<W 1 and W 2 >>is preferable.
In addition, in a case where Y C1 and Y C2 or Y C3 and Y C4 in Formula (I-W16-1) and Formula (I-W16-2) are integrated to form a ring structure, Y C1 and Y C2 or Y C3 and Y C4 preferably represent a group selected from Formula (Y—C-1) to Formula (Y—C-29),
(in the formulae, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and more preferably a group represented by Formula (Y—C-26).
<W 1 -M 2 -W 2 —C2>
In the compound in which <n1 represents 0, and n2 and n3 represent 1>, in a case of significantly considering storage stability of a composition, alignment defects, when a film-shaped polymer is prepared and irradiated with ultraviolet light, a group represented by W 1 and W 2 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis, among General Formula (I-W1) and General Formula (I-W2) shown in the section <<W 1 and W 2 >>.
In General Formula (I-W1) and General Formula (I-W2), V 1 , V 2 , V 3 , and V 4 preferably each independently represent a group represented by Formula (V-1) to Formula (V-15) described in the section <<W 1 and W 2 >> (in the formulae, in a case of including Y 1 , Y 1 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis described in the section <<W 1 and W 2 >>), a single bond, a double bond, —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, and —CH 2 —OCO—, more preferably each independently represent Formula (V-1), Formula (V-2), Formula (V-3), Formula (V-4), Formula (V-5), Formula (V-6), Formula (V-7), Formula (V-11), a single bond, or a double bond, even more preferably each independently represent Formula (V-1), Formula (V-2), Formula (V-3), Formula (V-4), Formula (V-5), or a single bond, and still more preferably each independently represent a single bond.
In General Formula (I-W1) and General Formula (I-W2), B 1 , B 2 , and B 3 preferably each independently represent a group selected from Formula (B-1) to Formula (B-21)
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and a single bond. B 1 , B 2 , and B 3 are preferably a group selected from Formula (B-4), Formula (B-8), Formula (B-11), Formula (B-12), and a single bond, and more preferably a group selected from Formula (B-4), Formula (B-8), and a single bond. More specifically, B 1 , B 2 , and B 3 are preferably a group selected from Formula (B-4-1), Formula (B-8-6), Formula (B-8-7), Formula (B-11-1), Formula (B-11-2), Formula (B-12-1), Formula (B-12-2) shown in the section <<W 1 and W 2 >>, and a single bond, more preferably a group selected from Formula (B-4-1), Formula (B-8-6), Formula (B-8-7), and a single bond, and even more preferably a group selected from Formula (B-4-1) and a single bond.
<W 1 -M 2 -W 1 —C3>
In the compound in which <n1 represents 0, and n2 and n3 represent 1>, in a case of significantly considering surface hardness, when a film-shaped polymer is prepared, and alignment defects, when the film is irradiated with ultraviolet light, a group represented by W 1 and W 2 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis described in the section <<W 1 and W 2 >>.
V 1 , V 2 , V 3 , and V 4 preferably each independently represent a group represented by Formula (V-1) to Formula (V-15) described in the section <<W 1 and W 2 >> (in the formulae, in a case of including Y 1 , Y 1 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis described in the section <<W 1 and W 2 >>), a single bond, a double bond, —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, and —CH 2 —OCO—, more preferably each independently represent Formula (V-1), Formula (V-2), Formula (V-6), Formula (V-8), Formula (V-9), Formula (V-10), a single bond, —CH 2 —, —COO—, —OCO—, —CS—NH—, —NH—CS—, or —CH 2 CH 2 —, even more preferably each independently represent Formula (V-6), Formula (V-8), Formula (V-9), —CH 2 —, —COO—, or —OCO—, and still more preferably each independently represent Formula (V-8) or Formula (V-9).
B 1 , B 2 , and B 3 preferably each independently represent a group selected from Formula (B-1) to Formula (B-21)
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and a single bond. B 1 , B 2 , and B 3 are preferably a group selected from Formula (B-3), Formula (B-4), Formula (B-7), Formula (B-11), Formula (B-12), and a single bond, and more preferably a group selected from Formula (B-4), Formula (B-12), and a single bond. More specifically, B 1 , B 2 , and B 3 are preferably a group selected from Formula (B-3-2), Formula (B-4-1), Formula (B-7-9), Formula (B-7-11), Formula (B-11-1), Formula (B-12-4) shown in the section <<W 1 and W 2 >>, and a single bond, more preferably a group selected from Formula (B-4-1), Formula (B-12-4), and a single bond, and even more preferably a group selected from Formula (B-4-1) and a single bond.
<R 3 and R 4 >
In the compound in which <n1 represents 0, and n2 and n3 represent 1>, M 2 , W 1 , and W 1 described above are preferably suitably selected and the following groups are preferably respectively used for R 3 and R 4 .
R 3 represents a group represented by Formula (I-R).
(In the formula, P represents a polymerizable group, S represents a spacer group or a single bond, in a case where a plurality of S is present, these may be the same as each other or different from each other, X represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of X is present in the compound, these may be the same as each other or different from each other (provided that P—(S—X) k — does not include a —O—O— bond), k represents an integer of 0 to 10.) R 4 preferably represent a group selected from the group represented by Formula (I-R) and R 5 (in the formula, R 5 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom). Both R 3 and R 4 are particularly preferably a group represented by Formula (I-R), and in this case, the preferable groups and numerical values shown in the section of <<R 1 , R 2 , R 3 , and R 4 >> are respectively applied to P, S, X, and k.
Compound in Which <<n1 and n2 Represent 0 and n3 Represents 2 to 1,000>>
<W 1 -D1>
In the compound in which <n1 and n2 represent 0 and n3 represents 2>, evenness of film thickness or adhesiveness, when a film-shaped polymer is prepared, is excellent due to the structure of the compound. Therefore, in General Formula (I), W 1 preferably represents a group selected from by Formula (I-W17-1) or Formula (I-W17-2).
(In the formulae, Y D1 represents a group including aromatic and/or nonaromatic carbon ring or heterocyclic ring having 1 to 80 carbon atoms which may be substituted, arbitrary carbon atoms of the carbon ring or the heterocyclic ring may be substituted with hetero atoms (provided that oxygen atoms are not directly bonded to each other). Y D2 represents a hydrogen atom or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, Y D2 may represent a group having 2 to 30 carbon atoms including at least one aromatic group, the group may be unsubstituted or substituted with one or more of substituents L. Y D represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, and in a case where a plurality of Y D is present, these may be the same as each other or different from each other. Alternatively, Y D2 may represent a group represented by P—(S—X) j —, P represents a polymerizable group, S represents a spacer group or a single bond, in a case where a plurality of S is present, these may be the same as each other or different from each other, X represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of X is present, these may be the same as each other or different from each other (provided that P—(S—X) j — does not include a —O—O— bond), j represents an integer of 0 to 10, Y D1 and Y D2 may be integrated to form a ring structure.)
In addition, from viewpoints of liquid crystal properties and ease of synthesis, Y D preferably represents a linear or branched alkyl group having 1 to 12 carbon atoms, in which one or more of arbitrary hydrogen atoms in the group may be substituted with a fluorine atom and one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, or —OCO—, more preferably represents a linear or branched alkyl group having 1 to 12 carbon atoms, in which one or more of arbitrary hydrogen atoms in the group may be substituted with a fluorine atom, and particularly preferably represents a linear alkyl group having 1 to 12 carbon atoms.
Further, Y D1 is preferably a group represented by Formula (B-1) to Formula (B-21).
(In the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.) Y D1 is more preferably a group selected from Formula (B-3), Formula (B-8), Formula (B-11), and Formula (B-12). More specifically, Y D1 is preferably a group selected from Formula (B-3-5), Formula (B-8-7), Formula (B-11-1), and Formula (B-12-1) shown in the section <<W 1 and W 2 >>, more preferably a group selected from Formula (B-8-7) and Formula (B-12-1), and even more preferably a group represented by Formula (B-8-7).
From viewpoints of availability of raw materials and ease of synthesis, in a case where Y D2 each independently represent a hydrogen atom, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and one or more of arbitrary hydrogen atoms may be substituted with a fluorine atom, Y D2 preferably each independently represent a hydrogen atom, or a linear or branched alkyl group having 1 to 12 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —CO—, —COO—, or —OCO—, and one or more of arbitrary hydrogen atoms may be substituted with a fluorine atom, more preferably each independently represent a hydrogen atom, or a linear or branched alkyl group having 1 to 12 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —CO—, —COO—, or —OCO—, even more preferably each independently represent a hydrogen atom, or a linear alkyl group having 1 to 8 carbon atoms, and still more preferably each independently represent a hydrogen atom. In addition, from viewpoints of availability of raw materials and ease of synthesis, in a case where Y D2 represents a group having 5 to 30 carbon atoms including at least one aromatic group, which may be unsubstituted or substituted with one or more of substituents L, Y D2 is preferably a group represented by Formula (B-1) to Formula (B-21),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and Y D2 is more preferably a group selected from Formula (B-3), Formula (B-8), Formula (B-11), and Formula (B-12). More specifically, Y D2 is preferably a group selected from Formula (B-3-5), Formula (B-8-7), Formula (B-11-1), and Formula (B-12-1) shown in the section <<W 1 and W 2 >>, more preferably a group selected from Formula (B-8-7) and Formula (B-12-1), and even more preferably a group represented by Formula (B-8-7).
In addition, in a case where Y D1 and Y D2 are integrated to form a ring structure, Y D1 and Y D2 preferably represent a group selected from Formula (Y-D-1) to Formula (Y-D-29),
(in the formulae, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and more preferably a group represented by Formula (Y-D-26).
<W 1 -D2>
In the compound in which <n1 and n2 represent 0 and n3 represents 2>, in a case of significantly considering haze and adhesiveness, when a film-shaped polymer is prepared, a group represented by W 1 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis, among General Formula (I-W1) shown in the section <<W 1 and W 2 >>.
In General Formula (I-W1), V 1 and V 2 preferably each independently represents the groups represented by Formula (V-1) to Formula (V-15) shown in the section <<W 1 and W 2 >> (in the formulae, in a case of including Y 1 , Y 1 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis described in the section <<W 1 and W 2 >>), a single bond, a double bond, —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, or —CH 2 —OCO—, more preferably represent Formula (V-1), Formula (V-2), Formula (V-3), Formula (V-4), Formula (V-5), Formula (V-6), Formula (V-7), Formula (V-8), Formula (V-9), a single bond, —COO—, or —OCO—, even more preferably represent Formula (V-5), Formula (V-8), Formula (V-9), or a single bond, and still more preferably represent a single bond.
In General Formula (I-W1), B 1 preferably each independently represents a group selected from Formula (B-1) to Formula (B-21).
(In the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L), and a single bond.
B 1 is preferably a group selected from Formula (B-4), Formula (B-8), Formula (B-11), Formula (B-12), and a single bond, and more preferably a group selected from Formula (B-8), Formula (B-12), and a single bond. More specifically, B 1 is preferably a group selected from Formula (B-4-1), Formula (B-8-2), Formula (B-8-7), Formula (B-11-1), Formula (B-12-1), Formula (B-12-4) shown in the section <<W 1 and W 2 >>, and a single bond, more preferably a group selected from Formula (B-8-2), Formula (B-12-4) and a single bond, and even more preferably a group represented by Formula (B-8-2).
<W 1 -D3>
In the compound in which <n1 and n2 represent 0 and n3 represents 2>, in a case of significantly considering haze and surface hardness, when a film-shaped polymer is prepared, a group represented by W 1 and W 2 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis, among General Formula (I-W1) shown in the section <<W 1 and W 2 >>.
In General Formula (I-W1), V 1 and V 2 preferably each independently represent the groups represented by Formula (V-1) to Formula (V-15) shown in the section <<W 1 and W 2 >> (in the formulae, in a case of including Y 1 , Y is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis described in the section <<W 1 and W 2 >>), a single bond, a double bond, —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, and —CH 2 —OCO—, more preferably represent Formula (V-5), Formula (V-6), Formula (V-7), Formula (V-8), Formula (V-9), Formula (V-10), a single bond, —COO—, —OCO—, —CS—NH—, and —NH—CS—, and even more preferably represent Formula (V-6), Formula (V-8), Formula (V-9), —COO—, and —OCO—.
In General Formula (I-W1), B 1 preferably each independently represents a group selected from Formula (B-1) to Formula (B-21),
(In the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and a single bond. B 1 is preferably a group selected from Formula (B-4), Formula (B-8), Formula (B-11), and a single bond, and more preferably a group selected from Formula (B-4) and a single bond. More specifically, B 1 is preferably a group selected from Formula (B-4-1), Formula (B-8-6), Formula (B-8-7), Formula (B-11-1) shown in the section <<W 1 and W 2 >>, and a single bond, and more preferably a group selected from Formula (B-4-1) and a single bond.
<-(M 2 ) 2 ->
In the compound in which <n1 and n2 represent 0 and n3 represents 2>, a haze value, evenness of film thickness, or adhesiveness, when a film-shaped polymer is prepared, are excellent due to the structure of the compound. Therefore, in General Formula (I), -(M 2 ) 2 - is preferably a group represented by General Formula (I-M3).
(In the formula, A 5 , A 6 , A 7 , and A8 being present each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, these groups may be unsubstituted or substituted with one or more of substituents L, and, in a case where a plurality of A 5 , A 6 , A 7 , and A 8 is present, these may be the same as each other or different from each other. Z 5 , Z 6 , Z 7 , and Z 8 being present each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of each of Z 5 , Z 6 , Z 7 , and Z 8 is present, these may be the same as each other or different from each other. X 1 and X 2 represent —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of X 2 is present in the compound, these may be the same as each other or different from each other, S 1 represents a single bond or a linear or branched alkylene group having 1 to 20 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, —OCO—, —OCO—O—, —CO—NH—, —NH—CO—, —CH═CH—, or —C≡C—, in a case where a plurality of S 1 is present, these may be the same as each other or different from each other (provided that X 1 —S 1 and S 1 —X 2 do not include a —O—O— bond.), kD represents an integer of 0 to 8, m5, m6, m7, and m8 each independently represent an integer of 0 to 5, total of m5, m6, m7, and m8 represents 0 to 6, T 3 and T 4 each independently represent a group selected from Formula (T-1) to Formula (T-22)
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L, and kD represents an integer of 1 to 20).) In addition, both T 3 and T 4 preferably represent one group selected from Formula (T-1) to Formula (T-22) and T 3 and T 4 more preferably represent the same group.
In addition, from viewpoints of availability of raw materials and ease of synthesis, A 5 , A 6 , A 7 , and A 8 preferably represent a 1,4-phenylene group, a 1,4-cyclohexylene group, or a naphthalene-2,6-diyl group which are not substituted or may be substituted with one or more substituent L, more preferably each independently represent a group selected from Formula (A-D-1) to Formula (A-D-11),
even more preferably each independently represent a group selected from Formula (A-D-1) to Formula (A-D-8), and particularly preferably each independently represent a group selected from Formula (A-D-1) to Formula (A-D-4).
In addition, from viewpoints of liquid crystal properties of the compound, availability of raw materials, and ease of synthesis, Z 5 , Z 6 , Z 7 , and Z 8 preferably each independently represent a single bond, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —CF═CF—, —C≡C—, or a single bond, more preferably each independently represent —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —C≡C—, or a single bond, even more preferably each independently represent —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond, and particularly preferably each independently represent —COO—, —OCO—, or a single bond.
In addition, from viewpoints of liquid crystal properties of the compound, ease of synthesis, and storage stability, m5, m6, m7, and m8 preferably each independently represent an integer of 1 to 4, more preferably each independently represent an integer of 1 to 3, and particularly preferably each independently represent 1 or 2. The total of m5, m6, m7, and m8 preferably each independently represents an integer of 2 to 4.
In addition, S-preferably each independently represents a linear alkylene group having 1 to 20 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, —OCO—, —OCO—O—, —CO—NH—, —NH—CO—, —CH═CH—, or —C≡C—, more preferably each independently represents a linear alkylene group having 1 to 12 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, or —OCO—, and even more preferably each independently represents a linear alkylene group having 1 to 6 carbon atoms.
In addition, X 1 and X 2 preferably represent —O—, —CO—, —COO—, —OCO—, —CO—NH—, —NH—CO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, or a single bond and more preferably represent —O—, —COO—, —OCO—, or a single bond.
In addition, kD preferably represents an integer of 0 to 4, more preferably represents an integer of 0 to 2, even more preferably represents 1 or 2, and still more preferably represents 1.
<-(M 2 ) 2 -D1>
In the compound in which <n1 and n2 represent 0 and n3 represents 2>, in a case of significantly considering storage stability of the composition, adhesiveness, when a film-shaped polymer is prepared, and appearance after ultraviolet light irradiation, or in a case of significantly considering evenness of film thickness and unevenness of alignment, when a film-shaped polymer is prepared, in General Formula (I-M3), T 3 and T 4 each independently represent a group selected from Formula (T2-1) to Formula (T2-10).
These groups preferably represent a group which may be unsubstituted or substituted with one or more of substituents L, and more preferably represent a group represented by Formula (T2-1) and Formula (T2-2). In addition, both T 3 and T 4 preferably represent one group selected from Formula (T2-1) to Formula (T2-10) and T 3 and T 4 more preferably represent the same group.
<-(M 2 ) 2 -D2>
In the compound in which <n1 and n2 represent 0 and n3 represents 2>, in a case of significantly considering haze and adhesiveness, when a film-shaped polymer is prepared, in General Formula (I-M3), T 3 's each independently represent a group selected from Formula (T2-11) to Formula (T2-27),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L.), Formula (T2-28) to Formula (T2-31),
(in the formulae, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L.), Formula (T2-32),
(in the formula, a bonding site may be at an arbitrary position, at least one —CH 2 — is each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L.), and Formula (T2-33) or Formula (T2-34),
(in the formulae, a bonding site may be at an arbitrary position, at least one —CH═ is each independently substituted with —N═. In addition, these groups may be unsubstituted or substituted with one or more of L.). In General Formula (I-M3), T 4 preferably represents a group selected from Formula (T2-1) to Formula (T2-10) or Formula (T2-11) to Formula (T2-34).
In addition, T 3 more preferably represents a group selected from Formula (T2-35) to Formula (T2-41),
(in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), even more preferably represents a group selected from Formula (T2-36), Formula (T2-40), and Formula (T2-41), and still more preferably represents Formula (T2-36). In addition, both T 3 and T 4 preferably represent a group selected from Formula (T2-35) to Formula (T2-41), more preferably represent a group selected from Formula (T2-36), Formula (T2-40), and Formula (T2-41), and still more preferably represent Formula (T2-36).
<-(M 2 ) 2 -D3>
In the compound in which <n1 and n2 represent 0 and n3 represents 2>, in a case of significantly considering haze and surface hardness, when a film-shaped polymer is prepared, T 3 preferably represents an acyclic group having 1 to 80 carbon atoms which may be substituted, and arbitrary carbon atoms of the acyclic group may be substituted with hetero atoms.
In addition, in General Formula (I-M3), T 3 preferably represents Formula (T-22)
(in the formula, a bonding site may be at an arbitrary position, arbitrary —CH 2 — may be each independently substituted with —O—, —S—, —NR— (in the formula, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L, and k1 represents an integer of 1 to 20.), preferably represents a group selected from Formula (T-22-1) or Formula (T-22-2),
(in the formulae, arbitrary —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formula, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L, and k131 to k134 represent an integer of 0 to 20), and more preferably represents Formula (T-22-1). It is even more preferable that k131 and k132 in Formula (T-22-1) represent 1. In addition, both T 3 and T 4 preferably represent a group represented by Formula (T-22), more preferably represent a group selected from Formula (T-22-1) or Formula (T-22-2), and even more preferably represent Formula (T-22-1).
<R 3 and R 4 >
In the compound in which <n1 and n2 represent 0 and n3 represents 2>, M 2 and W 1 described above are preferably suitably selected and the following groups are preferably respectively used as R 3 and R 4 . R 3 represents a group represented by Formula (I-R).
(In the formula, P represents a polymerizable group, S represents a spacer group or a single bond, in a case where a plurality of S is present, these may be the same as each other or different from each other, X represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of X is present in the compound, these may be the same as each other or different from each other (provided that P—(S—X) k — does not include a —O—O— bond), k represents an integer of 0 to 10.) R 4 preferably represents a group selected from the group represented by Formula (I-R) and R 5 (in the formula, R 5 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom). Both R 3 and R 4 are particularly preferably a group represented by Formula (I-R), and in this case, the preferable groups and numerical values shown in the section of <<R 1 , R 2 , R 3 , and R 4 >> are respectively applied to P, S, X, and k.
In the compound in which n3 represents 3 to 1,000 in the compound in which <n1 and n2 represent 0 and n3 represents 2 to 1,000>, haze, appearance after ultraviolet light irradiation, and alignment defects, when a film-shaped polymer is prepared, are excellent due to the structure of the compound. Therefore, in General Formula (I), the preferable groups and numerical values shown in the sections of <W 1 -D1>, <W 1 -D2>, and <W 1 -D3> are applied to W 1 . In addition, in General Formula (I), the preferable groups and numerical values shown in the sections of <-(M 2 ) 2 -D1>, <-(M 2 ) 2 -D2>, and <-(M 2 ) 2 -D3> are applied to -(M 2 ) n3 -.
In a case of significantly considering reverse dispersibility, the compound represented by General Formula (I) is preferably a compound represented by General Formula (I-z1) and/or General Formula (I-z2).
More specifically, in a case of significantly considering reverse dispersibility, solubility in a solvent, ease of synthesis, availability of raw materials, liquid crystal properties, hardening shrinkage in a case where a film is obtained, and reduced warp, a compound represented by General Formula (I) is preferably a compound represented by General Formula (I-z1).
In the formula, P z1 represents a polymerizable group and preferably represents a group selected from Formula (P-1) to Formula (P-20), and the polymerizable groups are polymerized by radical polymerization, radical addition polymerization, cation polymerization, and anion polymerization. Particularly, in a case of performing ultraviolet ray polymerization as a polymerization method, Formula (P-1), Formula (P-2), Formula (P-3), Formula (P-4), Formula (P-5), Formula (P-7), Formula (P-11), Formula (P-13), Formula (P-15), or Formula (P-18) is preferable, Formula (P-1), Formula (P-2), Formula (P-7), Formula (P-11), or Formula (P-13) is more preferable, Formula (P-1), Formula (P-2), or Formula (P-3) is even more preferable, and Formula (P-1) or Formula (P-2) is particularly preferable. S z1 represents a spacer group or a single bond, and in a case where a plurality of S z1 is present, these may be the same as each other or different from each other. From viewpoints of liquid crystal properties, availability of raw materials, and ease of synthesis, in a case where a plurality of S z1 is present, these may be the same as each other or different from each other, and S z1 's preferably each independently represent an alkylene group having 1 to 20 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, or —C≡C—, and a single bond. In a case where a plurality of S z1 is present, these may be the same as each other or different from each other, and S z1 's more preferably each independently represent a linear alkylene group having 1 to 20 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, —OCO—, or —OCO—O—, or a single bond. In a case where a plurality of S z1 is present, these may be the same as each other or different from each other, and S z1 's even more preferably each independently represent a linear alkylene group having 1 to 12 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, still more preferably each independently represent a linear alkylene group having 1 to 12 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, and particularly preferably represent a linear alkylene group having 1 to 12 carbon atoms. X z1 represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, and in a case where a plurality of X is present, these may be the same as each other or different from each other (provided that P z1 —(S z1 —X z1 ) kz — does not include a —O—O— bond). From viewpoints of availability of raw materials and ease of synthesis, in a case where a plurality of X z1 is present, these may be the same as each other or different from each other, X z1 's preferably each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond, more preferably each independently represent —O—, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond. In a case where a plurality of X z1 is present, these may be the same as each other or different from each other, and X z1 's particularly preferably each independently represent —O—, —COO—, —OCO—, or a single bond. A z1 and A z2 each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, these groups may be unsubstituted or substituted with one or more of L described above, and, in a case where a plurality of each of A z1 and A z2 is present, these may be the same as each other or different from each other. The preferable structure of A z1 and A z2 is the same as that in a case of A 1 , A 2 , A 3 , and A 4 . Z z1 and Z z2 each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of each of Z z1 and Z z2 is present, these may be the same as each other or different from each other. From viewpoints of liquid crystal properties of the compound, availability of raw materials, and ease of synthesis, Z z1 and Z z2 preferably each independently represent a single bond, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —CF═CF—, —C≡C—, or a single bond, more preferably each independently represent —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —C≡C—, or a single bond, even more preferably each independently represent —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond, still more preferably each independently represent —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond, and particularly preferably each independently represent —OCH 2 —, —CH 2 O—, —COO—, —OCO—, or a single bond.
M z represents a group selected from Formula (M-z-1) to Formula (M-z-8).
These groups may be unsubstituted or substituted with one or more of L Mz . L Mz represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, and in a case where a plurality of L Mz is present, these may be the same as each other or different from each other. From viewpoints of availability of raw materials and ease of synthesis, M z preferably each independently represents a group selected from Formula (M-z-1) or Formula (M-z-2) which may be unsubstituted or substituted with one or more of L Mz , or Formula (M-z-3) to Formula (M-z-6) which may not be substituted, more preferably represents a group selected from Formula (M-z-1) or Formula (M-z-2) which may be unsubstituted or substituted with one or more of L Mz , and particularly preferably represents a group selected from Formula (M-z-1) or Formula (M-z-2) which may not be substituted. R z1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a cyano group, a nitro group, an isocyano group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—, —CF═CF—, or —C≡C—, and one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom. From viewpoints of liquid crystal properties and ease of synthesis, R z1 preferably represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, or a linear or branched alkyl group having 1 to 12 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, —OCO—, or —O—CO—O—, more preferably a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, or a linear alkyl group or a linear alkoxy group having 1 to 12 carbon atoms, even more preferably a hydrogen atom, or a linear alkyl group or a linear alkoxy group having 1 to 12 carbon atoms, and particularly preferably a linear alkyl group or a linear alkoxy group having 1 to 12 carbon atoms. G z is preferably a compound represented by Formula (G-z-1) or Formula (G-z-2),
(in the formulae, R z2 represents a hydrogen atom, or a linear or branched alkyl group having 1 to 20 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, W z1 represents a group having 2 to 30 carbon atoms including at least one aromatic group, the group may be unsubstituted or substituted with one or more of L Wz . L Wz represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, and in a case where a plurality of L Wz is present, these may be the same as each other or different from each other. W Z2 represents a hydrogen atom, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom. Alternatively, W z2 may represent a group having 2 to 30 carbon atoms including at least one aromatic group, the group may be unsubstituted or substituted with one or more of substituents L Wz . W z1 and W z2 may be integrated to form a ring structure. kz represents an integer of 0 to 8. From viewpoints of liquid crystal properties, availability of raw materials, ease of synthesis, kz preferably represents an integer of 0 to 4, more preferably represents an integer of 0 to 2, even more preferably represents 0 or 1, and particularly preferably represents 1. mz1 and mz2 each independently represent an integer of 0 to 5 and mz1+mz2 represents an integer of 1 to 5. From viewpoints of liquid crystal properties, ease of synthesis, and storage stability, mz1 and mz2 preferably each independently represent an integer of 1 to 4, more preferably each independently represent an integer of 1 to 3, and particularly preferably represent 1 or 2. mz1+mz2 preferably represents an integer of 1 to 4 and particularly preferably represents 2 or 3), and more preferably represents a compound selected from General Formula (I-z1-A) to General Formula (I-z1-D).
(In the formulae, P z1 , S z1 , X z1 , kz, M z , G z , and R z1 represent the same meaning as those in General Formula (I-z1), A z11 and A z12 each independently represent the same meaning as A z1 in General Formula (I-z1), Z z11 and Z z12 each independently represent the same meaning as Z z1 in General Formula (I-z1), A z21 and A z22 each independently represent the same meaning as A z2 in General Formula (I-z1), and Z z21 and Z z22 each independently represent the same meaning as Z z2 in General Formula (I-z1).) From viewpoints of balance between refractive index anisotropy and reverse dispersibility, A z11 in General Formula (I-z1-A) and General Formula (I-z1-B) more preferably represents 1,4-phenylene group which may be unsubstituted or substituted with the substituent L, A z11 in General Formula (I-z1-C) and General Formula (I-z1-D) represents a 1,4-phenylene group which may be unsubstituted or substituted with the substituent L, A z12 more preferably represents a 1,4-cyclohexylene group which may be unsubstituted or substituted with the substituent L. In addition, A z21 in General Formula (I-z1-A) to General Formula (I-z1-D) represents a 1,4-phenylene group or a 1,4-cyclohexylene group which may be unsubstituted or substituted with the substituent L, and A z22 more preferably represents a 1,4-cyclohexylene group which may be unsubstituted or substituted with the substituent L. In General Formula (I-z1-A) to General Formula (I-z1-D), from viewpoints of liquid crystal properties, ease of synthesis, and storage stability, a compound represented by General Formula (I-z1-A) to General Formula (I-z1-C) is more preferable and a compound represented by General Formula (I-z1-A) or General Formula (I-z1-C) is particularly preferable. In a case where it is necessary to obtain a higher transition temperature T NI from a nematic phase to an isotropic phase, a compound represented by General Formula (I-z1-C) is particularly preferable.
From viewpoints of reverse dispersibility, solubility in a solvent, ease of synthesis, availability of raw materials, and liquid crystal properties, even more specifically, a compound represented by General Formula (I-z1) even more preferably represents a compound selected from General Formula (I-z1-A-1) to General Formula (I-z1-D-2).
(In the formulae, P z1 , S z1 , X z1 , kz, L, R z2 , W z1 , W z2 , and R z1 represent the same meaning as those in General Formula (I-z1), s represents an integer of 0 to 4, t represents an integer of 0 to 3, A z211 represents the same meaning as A z2 in General Formula (I-z1), and Z z111 and Z z121 each independently represent the same meaning as Z z1 in General Formula (I-z1). The preferable structure of each group is the same as that in General Formula (I-z1).) In General Formula (I-z1-A-1) to General Formula (I-z1-D-2), from viewpoints of liquid crystal properties, ease of synthesis, and storage stability, a compound represented by General Formula (I-z1-A-1) to General Formula (I-z1-C-2) is more preferable and a compound represented by General Formula (I-z1-A-1), General Formula (I-z1-A-2), General Formula (I-z1-C-1), or General Formula (I-z1-C-2) is particularly preferable. In a case where it is necessary to obtain reverse wavelength dispersibility of a short wavelength side, a compound represented by General Formula (I-z1-A-1) or General Formula (I-z1-C-1) is particularly preferable. In a case where it is necessary to obtain balance between reverse wavelength dispersibility and refractive index anisotropy, a compound represented by General Formula (I-z1-A-2) or General Formula (I-z1-C-2) is particularly preferable. In a case where it is necessary to obtain a higher transition temperature T NI from a nematic phase to an isotropic phase, a compound represented by General Formula (I-z1-C-1) or General Formula (I-z1-C-2) is particularly preferable. In a case where it is necessary to obtain reverse wavelength dispersibility of a long wavelength side, a compound represented by General Formula (I-z1-C-1) is particularly preferable.
In addition, W z1 particularly preferably represents a group selected from Formula (W-a-1) to Formula (W-a-6).
(In the formulae, r represents an integer of 0 to 5, s represents an integer of 0 to 4, and t represents an integer of 0 to 3.)
In addition, R z2 is more preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which is not substituted or substituted with one or more of F, and particularly preferably a hydrogen atom.
Further, in a case of significantly considering reverse dispersibility and liquid crystal properties, W z2 is preferably a hydrogen atom.
In a case of significantly considering a degree how hardly a change in quality occurs, in a case the compound is dissolved in an organic solvent and stored for a long period of time, a degree how hardly a change in quality occurs, in a case the compound is added to the composition and stored for a long period of time, or stability of a phase difference in a case where a film is obtained, W z2 preferably represents a linear or branched alkyl group having 1 to 20 carbon atoms, in which one or more of arbitrary hydrogen atoms in the group may be substituted with a fluorine atom and one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —CO—, —COO—, or —OCO—, or a group represented by —(X z4 —S z4 ) kz —P z4 (in the formula, P z4 represents the same meaning as P z1 , and S z4 represents the same meaning as S z1 , and X z4 represents the same meaning as X z1 ). Among the groups described above, W 2 more preferably represents a linear alkyl group having 1 to 12 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, or a group represented by —(X z4 —S z4 ) kz —P z4 . More specifically, from a viewpoint of ease of synthesis, W z2 more preferably represents a linear or branched alkyl group having 1 to 20 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, or a group represented by —(X z4 —S z4 ) kz —P z4 , and even more preferably represents a linear alkyl group having 1 to 12 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, or a group represented by —(X z4 —S z4 ) kz —P z4 .
In a case of significantly considering balance between reverse dispersibility, high refractive index anisotropy, and high liquid crystal properties, in a case where the compound is added to the composition, a degree how hardly a change in quality occurs, in a case the compound is dissolved in an organic solvent and stored for a long period of time, a degree how hardly a change in quality occurs, in a case the compound is added to the composition and stored for a long period of time, or stability of a phase difference in a case where a film is obtained, W z2 is preferably a compound represented by General Formula (I-z2).
(In the formula, kz, M z , and G z represent the same meaning as those in General Formula (I-z1), P z2 and P z3 each independently represent the same meaning as P z1 in General Formula (I-z1), S z2 and S z3 each independently represent the same meaning as S z1 in General Formula (I-z1), X z2 and X z3 each independently represent the same meaning as X z1 in General Formula (I-z1), A z3 and A z4 each independently represent the same meaning as A z1 and A z2 in General Formula (I-z1), Z z3 and Z z4 each independently represent the same meaning as Z z1 and Z z2 in General Formula (I-z1), mz3 and mz4 each independently represent an integer of 0 to 5, and mz3+mz4 represents an integer of 1 to 5). In a case of significantly considering balance between reverse dispersibility, high refractive index anisotropy, and high liquid crystal properties, when the compound is added to the composition, W z2 is preferably General Formula (I-z2-A) and General Formula (I-z2-B).
(In the formulae, P z2 , P z3 , S z2 , S z3 , M z , and G z represent the same meaning as those in General Formula (I-z2), A z31 , A z42 , A z33 , and A z43 each independently represent a 1,4-phenylene group, the group may be unsubstituted or substituted with one or more of substituents L z11 . L z11 represents a fluorine atom, a chlorine atom, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —CO—, —COO—, or —OCO—, and one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom. In a case where a plurality of L z11 are present in the compound, these may be the same as each other or different from each other. A z32 and A z41 represent a 1,4-cyclohexylene group, Z z31 and Z z42 each independently represent —OCH 2 —, —CH 2 O—, —COO—, —OCO—, or a single bond, Z z32 , Z z41 , Z z33 , and Z z43 each independently represent —OCH 2 —, —CH 2 O—, —COO—CH 2 CH 2 —, —CH 2 CH 2 —OCO—, —COO—, or —OCO—, and at least one of Z z32 and Z z41 and at least one of Z z33 and Z z43 represent a group selected from —OCH 2 —, —CH 2 O—, —COO—CH 2 CH 2 —, or —CH 2 CH 2 —OCO—.)
In a case of significantly considering balance between reverse dispersibility, high refractive index anisotropy, and high liquid crystal properties, in a case where the compound is added to the composition, a degree how hardly a change in quality occurs, in a case the compound is dissolved in an organic solvent and stored for a long period of time, a degree how hardly a change in quality occurs, in a case the compound is added to the composition and stored for a long period of time, or stability of a phase difference in a case where a film is obtained, W z2 is preferably a compound represented by General Formula (I-z2-A-1).
(In the formula, P z2 , P z3 , S z2 , S z3 , X z2 , X z3 , M z , R z2 , W z1 represent the same meaning as those in General Formula (I-z1), A z311 and A z421 each independently represent a 1,4-phenylene group, the group may be unsubstituted or substituted with one or more of substituents L z11 . A z321 and A z411 represent a 1,4-cyclohexylene group, Z z311 and Z z421 each independently represent —OCH 2 —, —CH 2 O—, —COO—, or —OCO—, Z z321 and Z z411 each independently represent —OCH 2 —, —CH 2 O—, —COO—CH 2 CH 2 —, —CH 2 CH 2 —OCO—, —COO—, or —OCO—, and at least one of Z z321 and Z z411 particularly preferably represents a group selected from —OCH 2 —, —CH 2 O—, —COO—CH 2 CH 2 —, or —CH 2 CH 2 —OCO—. W z21 represents a group selected from a linear or branched alkyl group having 1 to 20 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, or a group represented by —(X z4 —S z4 ) kz —P z4 .) The preferable structure of W z1 is the same as that described above.
Specifically, the compounds represented by General Formula (I) are preferably compounds represented by the following formulae.
The total content of the reverse dispersible compound represented by General Formula (I) is preferably 10% to 95% by mass, more preferably 30% to 95% by mass, and particularly preferably 60% to 95% by mass, with respect to the total amount of the polymerizable compound used in the polymerizable composition (that is, the total content of the reverse dispersible compound represented by General Formula (I) and the total content of the compound represented by General Formula (II)).
<<General Formula (II)>>
In the present invention, a compound represented by General Formula (II) is included as an essential component.
In the formula, P 21 represents a polymerizable functional group, S 21 represents an alkylene group having 1 to 18 carbon atoms (hydrogen atoms in the alkylene group may be substituted with one or more halogen atoms, a CN group, or an alkyl group having 1 to 8 carbon atoms including a polymerizable functional group, and one CH 2 group or two or more of (—CH 2 —)'s that are not adjacent to each other present in this group may be each independently substituted with —O—, —COO—, —OCO—, or —OCO—O—), X 21 represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF—S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond (provided that P 21 —S 21 and S 21 —X 21 do not include a —O—O—, —O—NH—, —S—S—, and —O—S— group), q1 represents 0 or 1, MG represents a mesogenic group, R 21 represents a hydrogen atom, a halogen atom, a cyano group, or a linear or a branched alkyl group having 1 to 12 carbon atoms, the alkyl group may be linear or branched, and one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other of the alkyl group may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—. Alternatively, R 21 represents General Formula (II-a).
[Chem. 200]
—(X 22 —S 22 ) q2 —P 23 (II-a)
(In the formula, P 23 represents a polymerizable functional group, S 22 represents a component which is the same as that defined in the description regarding S 21 , X 22 represents a component which is the same as that defined in the description regarding X 21 (provided that P 23 —S 22 and S 22 —X 22 do not include a —O—O—, —O—NH—, —S—S—, and —O—S— group), q 2 represents 0 or 1). A mesogenic group represented by MG described above is represented by General Formula (II-b).
[Chem. 201]
-(B1-Z1) r1 —B2-Z2-B3- (II-b)
(In the formula, B1, B2, and B3 each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a 1,4-cyclohexenyl group, a tetrahydropyran-2,5-diyl group, a 1,3-dioxane-2,5-diyl group, a tetrahydrothiopyran-2,5-diyl group, a 1,4-bicyclo (2,2,2) octylene group, a decahydronaphthalene-2,6-diyl group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a pyrazine-2,5-diyl group, a thiophene-2,5-diyl group-, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a 2,6-naphthylene group, a phenanthrene-2,7-diyl group, a 9,10-dihydrophenanthrene-2,7-diyl group, a 1,2,3,4,4a,9,10a-octahydrophenanthrene-2,7-diyl group, a 1,4-naphthylene group, a benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl group, a benzo[1,2-b:4,5-b′]diselenophene-2,6-diyl group, a [1]benzothieno[3,2-b]thiophene-2,7-diyl group, a [1]benzoselenopheno[3,2-b] selenophene-2, 7-diyl group, or a fluorene-2,7-diyl group. As a substituent, one or more of F, Cl, CF 3 , OCF 3 , a CN group, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkanoyl group having 1 to 8 carbon atoms, an alkanoyloxy group having 1 to 8 carbon atoms, an alkoxycarbonyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkenyloxy group having 2 to 8 carbon atoms, an alkenoyl group having 2 to 8 carbon atoms, an alkenoyloxy group having 2 to 8 carbon atoms, and/or General Formula (II-c)
[Chem. 202]
—(X 23 ) q4 —(S 23 ) q3 —P 24 (II-c)
(in the formula, P 4 represents a reactive functional group, S 23 represents a component which is the same as that defined in the description regarding S 21 , X 23 represents —O—, —COO—, —OCO—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 OCO—, —COOCH 2 CH 2 —, —OCOCH 2 CH 2 —, or a single bond, q 3 represents 0 or 1, and q 4 represents 0 or 1 (provided that P 24 —S 23 and S 23 —X 23 do not include a —O—O—, —O—NH—, —S—S— or —O—S— group).) may be included. B1, B2, and B3 are preferably a 1,4-cyclohexylene group, a 1,4-cyclohexenyl group, a tetrahydropyran-2,5-diyl group, a 1,3-dioxane-2,5-diyl group, a tetrahydrothiopyran-2,5-diyl group, a 1,4-bicyclo (2,2,2) octylene group, or a decahydronaphthalene-2,6-diyl group (as a substituent, one or more of F, Cl, CF 3 , OCF 3 , a CN group, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkanoyl group having 1 to 8 carbon atoms, an alkanoyloxy group having 1 to 8 carbon atoms, an alkoxycarbonyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkenyloxy group having 2 to 8 carbon atoms, an alkenoyl group having 2 to 8 carbon atoms, an alkenoyloxy group having 2 to 8 carbon atoms, and/or General Formula (II-c)), Z1 and Z2 each independently represent —COO—, —OCO—, —CH 2 CH 2 —, —OCH 2 —, —CH 2 O—, —CH═CH—, —C≡C—, —CH═CHCOO—, —OCOCH═CH—, —CH 2 CH 2 COO—, —CH 2 CH 2 OCO—, —COOCH 2 CH 2 —, —OCOCH 2 CH 2 —, —C═N—, —N═C—, —CONH—, —NHCO—, —C(CF 3 ) 2 —, an alkyl group having 2 to 10 carbon atoms which may include a halogen atom, or a single bond, r1 represents 0, 1, 2, or 3, and in a case where a plurality of each of B1 and Z1 is present, these may be respectively the same as each other or different from each other, and r1 is preferably 0.)
In the present invention, as a preferable halogen atom, a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom is preferable, a fluorine atom or a chlorine atom is more preferable, and a fluorine atom is particularly preferable. The same applies to a halogen atom described below.
P 22 , P 23 , and P 24 preferably each independently represent a substituent selected from a polymerizable group represented by Formula (P-2-1) to Formula (P-2-20).
From a viewpoint of increasing polymerizability, among these polymerizable functional groups, Formula (P-2-1), Formula (P-2-2), Formula (P-2-7), Formula (P-2-12), and Formula (P-2-13) are preferable, and Formula (P-2-1) and Formula (P-2-2) are more preferable.
(Monofunctional Polymerizable Liquid Crystal Compound)
Among the compounds represented by General Formula (II), a compound represented by General Formula (II-2-1) is preferable, as a monofunctional polymerizable liquid crystal compound including one polymerizable functional group in a molecule.
[Chem. 204]
P 21 —(S 21 —X 21 ) q1 -MG-R 21 (II-2-1)
In the formulae, P 21 , S 21 , X 21 , q1, and MG respectively represent the same definition as those in General Formula (II), R 21 represents a hydrogen atom, a halogen atom, a cyano group, or a linear or branched alkyl group having 1 to 12 carbon atoms or a linear or branched alkenyl group having 1 to 12 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —NH—, —N(CH 3 )—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, one hydrogen atom or two or more hydrogen atoms in the alkyl group and the alkenyl group may be substituted with halogen atoms or cyano groups, and in a case where a plurality of atoms are substituted, these may be the same as each other or different from each other. The monofunctional polymerizable liquid crystal compound has characteristics in which polarities of both ends are different from each other, compared to a multifunctional polymerizable liquid crystal compound. In a case where the polymerizable composition of the present invention is applied onto a base material, a hydrophobic group tends to easily appear on a side of an air interface. Accordingly, by adding the monofunctional polymerizable liquid crystal compound and suitably selecting the kind of a surfactant which will be described later and an amount thereof added, it is possible to control an angle of alignment of polymerizable liquid crystals in the air interface, that is, a tilt angle.
As examples of General Formula (II-2-1), compounds represented by General Formulae (II-2-1-1) to (II-2-1-4) can be used, but there is no limitation to the general formulae below.
[Chem. 205]
P 21 —(S 21 —X 21 ) q1 —B2-Z2-B3-R 21 (II-2-1-1)
P 21 —(S 21 —X 21 ) q1 -B11-Z11-B2-Z2-B3-R 21 (II-2-1-2)
P 21 —(S 21 —X 21 ) q1 -B11-Z11-B12-Z12-B2-Z2-B3-R 21 (II-2-1-3)
P 21 —(S 21 —X 21 ) q1 -B11-Z12-Z12-B13-Z13-B2-Z2-B3-R 21 (II-2-1-4)
In the formulae, P 21 , S 21 , X 21 , and q1 respectively represent the same definition as those in General Formula (II) (in a case of controlling tilt, S 21 is preferably an alkylene group having 3 to 18 carbon atoms (one or more of arbitrary hydrogen atoms in the alkylene group may be substituted with a halogen atom, a cyano group, or an alkyl group having 1 to 8 carbon atoms including a polymerizable functional group, and one CH 2 group or two or more of (—CH 2 —)'s that are not adjacent to each other present in this group may be each independently substituted with —O—, —COO—, —OCO—, or —OCO—O—).
B11, B12, B13, B2, and B3 represent the same definition as B1 to B3 of General Formula (II-b), and these may be respectively the same as each other or different from each other.
Z1, Z12, Z13, and Z2 represent the same definition as Z1 to Z3 of General Formula (II-b), and these may be respectively the same as each other or different from each other. R 21 represents a hydrogen atom, a halogen atom, a cyano group, or a linear or branched alkyl group having 1 to 12 carbon atoms or a linear or branched alkenyl group having 1 to 12 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —NH—, —N(CH 3 )—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, one hydrogen atom or two or more hydrogen atoms in the alkyl group and the alkenyl group may be substituted with halogen atoms or cyano groups, and in a case where a plurality of atoms are substituted, these may be the same as each other or different from each other. Meanwhile, in a case R 21 is a cyano group, S 21 is preferably an alkylene group having 3 to 18 carbon atoms (hydrogen atoms in the alkylene group may be substituted with one or more halogen atoms, a cyano group, or an alkyl group having 1 to 8 carbon atoms including a polymerizable functional group, one CH 2 group or two or more of (—CH 2 —)'s that are not adjacent to each other present in this group may be each independently substituted with —O—, —COO—, —OCO—, or —OCO—O—), from a viewpoint in that the tilt is easily controlled, in a case of having different polarities on both ends of the compound.
As the compounds represented by General Formulae (II-2-1-1) to (II-2-1-4), compounds represented by General Formula (II-2-1-1-1) to General Formula (II-2-1-1-32) are used, but there is no limitation thereto.
In the formulae, R c represents a hydrogen atom or a methyl group, m represents an integer of 0 to 18, n represents 0 or 1, R 21 represents the same definition as those in General Formulae (II-2-1-1) to (II-2-1-4), R 21 preferably represents a hydrogen atom, a halogen atom, a cyano group, or a linear alkyl group having 1 to 6 carbon atoms or a linear alkenyl group having 1 to 6 carbon atoms, in which one —CH 2 — may be substituted with —O—, —CO—, —COO—, or —OCO—, R 21 more preferably represents a halogen atom or a cyano group, and in a case where R 21 represents a cyano group, m is preferably an integer of 3 to 18, from a viewpoint in that the tilt is easily controlled, in a case of having different polarities on both ends of the compound, as described above.
The cyclic group described above may include one or more of F, Cl, CF 3 , OCF 3 , a CN group, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkanoyl group having 1 to 8 carbon atoms, an alkanoyloxy group having 1 to 8 carbon atoms, an alkoxycarbonyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkenyloxy group having 2 to 8 carbon atoms, an alkenoyl group having 2 to 8 carbon atoms, or an alkenoyloxy group having 2 to 8 carbon atoms, as a substituent.
More specifically, compounds represented by the following formulae are preferable.
The total content of the monofunctional polymerizable liquid crystal compound including one polymerizable functional group in one molecule is preferably 0% to 90% by mass, more preferably 0% to 85% by mass, and particularly preferably 0% to 80% by mass, with respect to total amount of the compound represented by General Formula (II) used. In a case of significantly considering alignment of an optically anisotropic body, the lower limit value is preferably equal to or greater than 5% by mass and more preferably equal to or greater than 10% by mass, and in a case of significantly considering hardness of a coated film, the upper limit value is preferably equal to or smaller than 80% by mass and more preferably equal to or smaller than 70% by mass.
(Bifunctional Polymerizable Liquid Crystal Compound)
Among the compounds represented by General Formula (II), a compound represented by General Formula (II-2-2) is preferable, as a bifunctional polymerizable liquid crystal compound including two polymerizable functional groups in a molecule.
[Chem. 213]
P 21 —(S 21 —X 21 ) q1 -MG-(X 22 —S 22 ) q2 P 23 (II-2-2)
In the formula, P 21 , S 21 , X 21 , q1, MG, X 22 , S 22 , q2, and P 23 respectively represent the same definition as those in General Formula (II). As examples of General Formula (II-2-2), compounds represented by General Formulae (II-2-2-1) to (II-2-2-4) can be used, but there is no limitation to General Formulae below.
[Chem. 214]
P 21 —(S 21 —X 21 ) q1 -B2-Z2-B3-(X 22 —S 22 ) q2 P 23 (II-2-2-1)
P 21 —(S 21 —X 21 ) q1 B11-Z11-B2-Z2-B3-(X 22 —S 22 ) q2 —P 23 (II-2-2-2)
P 21 —(S 21 —X 21 ) q1 -B11-Z11-BIZ B2-Z2-B23-(X 22 —S 22 ) q2 —P 23 (II-2-2-3)
P 21 —(S 21 —X 21 ) q1 —B11-Z11-B12-Z12-B13-Z13-B2-Z2-B3-(X 22 —S 22 ) q2 P 23 (II-2-2-4)
In the formulae, P 21 , S 21 , X 21 , q1, MG, X 22 , S 22 , q2, and P 23 respectively represent the same definition as those in General Formula (II), B11, B12, B13, B2, and B3 represent the same definition as B1 to B3 of General Formula (II-b), and these may be respectively the same as each other or different from each other. Z11, Z 12 , Z 13 , and Z2 represent the same definition as Z1 to Z3 of General Formula (II-b), and these may be respectively the same as each other or different from each other.
Among the compounds represented by General Formulae (II-2-2-1) to (II-2-2-4), it is preferable to use the compounds represented by General Formulae (II-2-2-2) to (II-2-2-4) having three or more of ring structures in the compound, because alignment of an optically anisotropic body to be obtained is excellent and hardenability is excellent. It is particularly preferable to use a compound represented by General Formula (II-2-2-2) having three or more of ring structures in the compound.
As the compounds represented by General Formulae (II-2-2-1) to (II-2-2-4), compounds represented by General Formula (1I-2-2-1-1) to General Formula (II-2-2-1-45) are used, but there is no limitation thereto.
In the formulae, R d and R e each independently represent a hydrogen atom or a methyl group, and the cyclic group may include one or more of F, Cl, CF 3 , OCF 3 , a CN group, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkanoyl group having 1 to 8 carbon atoms, an alkanoyloxy group having 1 to 8 carbon atoms, an alkoxycarbonyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkenyloxy group having 2 to 8 carbon atoms, an alkenoyl group having 2 to 8 carbon atoms, or an alkenoyloxy group having 2 to 8 carbon atoms, as a substituent.
m1 and m2 each independently represent an integer of 0 to 18, and n1, n2, n3, and n4 each independently represent 0 or 1.
More specifically, compounds represented by the following formulae are preferable.
The total content of the bifunctional polymerizable liquid crystal compound including two polymerizable functional groups in a molecule is preferably 10% to 100% by mass, more preferably 15% to 85% by mass, and particularly preferably 20% to 80% by mass, with respect to the total amount of the compound represented by General Formula (II) used. In a case of significantly considering hardness of a coated film, the lower limit value is preferably equal to or greater than 30% by mass and more preferably equal to or greater than 50% by mass, and in a case of significantly considering alignment of an optically anisotropic body, the upper limit value is preferably equal to or smaller than 85% by mass and more preferably equal to or smaller than 80% by mass.
(Multifunctional Polymerizable Liquid Crystal Compound)
As a multifunctional polymerizable liquid crystal compound including three or more of polymerizable functional groups, a compound including three polymerizable functional groups is preferably used. Among the compounds represented by General Formula (II), a compound represented by General Formula (1I-2-3) is preferable, as a multifunctional polymerizable liquid crystal compound including three polymerizable functional groups in a molecule.
In the formula, P 21 , S 21 , X 21 , q1, MG, X 22 , S 22 , q2, P 23 , X 23 , q4, S 23 , q3, P 24 respectively represent the same definition as those in General Formula (II). As examples of General Formula (II-2-3), compounds represented by General Formulae (II-2-3-1) to (II-2-3-8) can be used, but there is no limitation to General Formulae below.
In the formulae, P 21 , S 21 , X 21 , q1, MG, X 22 , S 22 , q2, P 23 , X 23 , q4, S 23 , q3, P 24 respectively represent the same definition as those in General Formula (II), B 31 , B 32 , B 22 , B 23 represent the same definition as B 21 to B 23 of General Formula (II-b), and these may be respectively the same as each other or different from each other. Z 52 , Z 53 , and Z 54 represent the same definition as Z 51 and Z 52 of General Formula (II-b), and these may be respectively the same as each other or different from each other.
As the compounds represented by General Formulae (II-2-3-1) to (II-2-3-5), compounds represented by General Formula (II-2-3-1-1) to General Formula (II-2-3-1-6) are used, but there is no limitation thereto.
In the formulae, R f , R g , and R h each independently represent a hydrogen atom or a methyl group, R i , R j , and R k each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a cyano group. In a case where these groups are an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, all of the groups may be unsubstituted or substituted with one halogen atom or two or more of halogen atoms, and the cyclic group may include one or more of F, Cl, CF 3 , OCF 3 , a CN group, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkanoyl group having 1 to 8 carbon atoms, an alkanoyloxy group having 1 to 8 carbon atoms, an alkoxycarbonyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkenyloxy group having 2 to 8 carbon atoms, an alkenoyl group having 2 to 8 carbon atoms, or an alkenoyloxy group having 2 to 8 carbon atoms, as a substituent.
m4 to m9 each independently represent an integer of 0 to 18, and n4 to n9 each independently represent 0 or 1.
One kind or two or more kinds of the multifunctional polymerizable liquid crystal compound including three or more of polymerizable functional groups can be used.
The total content of the multifunctional polymerizable liquid crystal compound including three or more of polymerizable functional groups in a molecule is preferably 0% to 80% by mass, more preferably 0% to 60% by mass, and particularly preferably 0% to 40% by mass, with respect to total amount of the compound represented by General Formula (II) used. In a case of significantly considering rigidity of an optically anisotropic body, the lower limit value is preferably equal to or greater than 10% by mass, more preferably equal to or greater than 20% by mass, and particularly preferably equal to or greater than 30% by mass. Meanwhile, in a case of significantly considering low curing shrinkage, the upper limit value is preferably equal to or smaller than 50% by mass, more preferably equal to or smaller than 35% by mass, and particularly preferably equal to or smaller than 20% by mass.
(Use of Plurality of Kinds of Polymerizable Liquid Crystal Compounds)
In the polymerizable liquid crystal composition of the present invention, a plurality of kinds of the polymerizable liquid crystal compounds are preferably mixed with each other and used. It is preferable that at least one kind or more of monofunctional polymerizable liquid crystal compound, at least one kind or more of bifunctional polymerizable liquid crystal compound, and/or multifunctional polymerizable liquid crystal compound are used in combination, because hardenability of an optically anisotropic body to be obtained is improved and excellent adhesiveness with a base material is obtained. It is more preferable that at least one kind or more of monofunctional polymerizable liquid crystal compound and at least one kind or more of bifunctional polymerizable liquid crystal compound are used in combination. Among these, when an optically anisotropic body is obtained by using the polymerizable liquid crystal composition of the present invention, in a case of further improving hardenability, as the bifunctional polymerizable liquid crystal compound, it is preferable to obtain a mixture of the polymerizable liquid crystal compounds by using the compound selected from (II-2-2-1) to (II-2-2-2) including two or three ring structures in the compound, and it is particularly preferable to obtain a mixture in which the compound represented by (II-2-1-1) and (II-2-2-1) including two ring structures are used in the compound in combination.
The total amount of the monofunctional polymerizable liquid crystal compound and the bifunctional polymerizable liquid crystal compound is preferably 70% by mass to 100% by mass and particularly preferably 80% by mass to 100% by mass, with respect to the total amount of the compound represented by General Formula (II) used.
The total content of the compound represented by General Formula (II) is preferably 5% to 90% by mass, more preferably 5% to 70% by mass, and particularly preferably 5% to 40% by mass, with respect to total amount of the polymerizable compound used in the polymerizable composition (that is, the total content of the reverse dispersible compound represented by General Formula (I) and the total content of the compound represented by General Formula (II)).
(Other Liquid Crystal Compounds)
In addition, a compound including a mesogenic group not including a polymerizable group may be added to the liquid crystal composition of the present invention, and compounds used in typical liquid crystal devices, for example, supertwisted nematic (STN) liquid crystal, twisted nematic (TN) liquid crystal, or thin film transistor (TFT) liquid crystal, are used.
Specifically, the compound including a mesogenic group not including a polymerizable functional group is preferably a compound represented by General Formula (5).
[Chem. 227]
R 51 -MG3-R 52 (5)
A mesogenic group represented by MG3 or mesogenic support group is a compound represented by General Formula (5-b).
[Chem. 228]
—Z0 d -(A1 d -Z1 d ) ne -A2 d -Z2 d -A3 d -Z3 d - (5-b)
(In the formula, A1 d , A2 d , and A3 d each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a 1,4-cyclohexenyl group, a tetrahydropyran-2,5-diyl group, a 1,3-dioxane-2,5-diyl group, a tetrahydrothiopyran-2,5-diyl group, a 1,4-bicyclo (2,2,2) octylene group, a decahydronaphthalene-2,6-diyl group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a pyrazine-2,5-diyl group, a thiophene-2,5-diyl group-, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a 2,6-naphthylene group, a phenanthrene-2,7-diyl group, a 9,10-dihydrophenanthrene-2,7-diyl group, a 1,2,3,4,4a,9,10a-octahydrophenanthrene-2,7-diyl group, a 1,4-naphthylene group, a benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl group, a benzo[1,2-b:4,5-b′]diselenophene-2,6-diyl group, a [I]benzothieno[3,2-b]thiophene-2,7-diyl group, a [1]benzoselenopheno[3,2-b] selenophene-2,7-diyl group, or a fluorene-2,7-diyl group. As a substituent, one or more of F, Cl, CF 3 , OCF 3 , a CN group, an alkyl group, an alkoxy group, an alkanoyl group, or an alkanoyloxy group having 1 to 8 carbon atoms, an alkenyl group, an alkenyloxy group, an alkenoyl group, or an alkenoyloxy group having 2 to 8 carbon atoms. Z0 d , Z1 d , Z2 d , and Z3 d each independently represent —COO—, —OCO—, —CH 2 CH 2 —, —OCH 2 —, —CH 2 O—, —CH═CH—, —C≡C—, —CH═CHCOO—, —OCOCH═CH—, —CH 2 CH 2 COO—, —CH 2 CH 2 OCO—, —COOCH 2 CH 2 —, —OCOCH 2 CH 2 —, —CONH—, —NHCO—, an alkylene group having 2 to 10 carbon atoms which may include a halogen atoms, or a single bond. n e represents 0, 1, or 2, R 51 and R 52 each independently represent a hydrogen atom, a halogen atom, a cyano group, or an alkyl group having 1 to 18 carbon atoms, the alkyl group may be substituted with one or more of halogen atoms or CN, and one CH 2 group or two or more of (—CH 2 —)'s that are not adjacent to each other present in this group may be each mutually independently substituted with —O—, —S—, —NH—, —N(CH 3 )—, —CO—, —COO—, —OCO—, —OCOO—, —SCO—, —COS—, or —C≡C—, in a state where oxygen atoms are not directly bonded to each other.)
Specifically, the following examples are shown, but there is no limitation.
Ra and Rb each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkenyl group having 1 to 6 carbon atoms, a cyano group. In a case where these groups are an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, all of the groups may be unsubstituted or substituted with one halogen atom or two or more of halogen atoms.
The total content of the compound including a mesogenic group is preferably 0% by mass to 20% by mass, with respect to the total amount of the total content of the reverse dispersible compound represented by General Formula (I) and the total content of the compound represented by General Formula (II). In a case of use, the total content is preferably equal to or greater than 1% by mass, preferably equal to or greater than 2% by mass, and preferably equal to or greater than 5% by mass, and preferably equal to or smaller than 15% by mass, and preferably equal to or smaller than 10% by mass.
(Other Components)
(Chiral Compound)
The polymerizable liquid crystal composition of the present invention can also include a polymerizable chiral compound which may exhibit liquid crystal properties or may be amorphous, in addition to the polymerizable compound represented by General Formula (II).
The polymerizable chiral compound used in the present invention preferably includes one or more of polymerizable functional groups. Examples of such a compound include a polymerizable chiral compound including chiral saccharide such as isosorbide, isomannit, or glucoside, a rigid part such as 1,4-phenylene group or 1,4-cyclohexylene group, and a polymerizable functional group such as a vinyl group, an acryloyl group, a (meth)acryloyl group, or a maleimide group, disclosed in JP-A-H11-193287, JP-A-2001-158788, JP-T-2006-52669, JP-A-2007-269639, JP-A-2007-269640, and JP-A-2009-84178, a polymerizable chiral compound formed of a terpenoid derivative, disclosed in JP-A-H8-239666, a polymerizable chiral compound formed of a mesogenic group and a spacer including a chiral part, disclosed in NATURE Vol. 35, pp. 467-469 (published 30, November 1995), and NATURE Vol. 392, pp. 476-479 (published 2, April, 1998), or a polymerizable chiral compound including a binaphthyl group disclosed in JP-T-2004-504285 and JP-A-2007-248945. Among these, a chiral compound having a great helical twisting power (HTP) is preferably used in the polymerizable liquid crystal composition of the present invention.
It is necessary that a blending amount of the polymerizable chiral compound is suitably adjusted in accordance with a helical induction power of the compound, and the blending amount is preferably 0% to 25% by mass, more preferably 0% to 20% by mass, and particularly preferably 0% to 15% by mass, with respect to the total amount of the total content of the reverse dispersible compound represented by General Formula (I) and the total content of the compound represented by General Formula (II).
As one example of General Formula of the polymerizable chiral compound, General Formulae (3-1) to (3-4) can be used, but there is no limitation to the general formulae.
In the formulae, SP 3a and SP 3b each independently represent an alkylene group having 0 to 18 carbon atoms, the alkylene group may be substituted with one or more of halogen atoms, a CN group, or an alkyl group having 1 to 8 carbon atoms including a polymerizable functional group, and one CH 2 group or two or more of (—CH 2 —)'s CH 2 groups that are not adjacent to each other present in this group may be each mutually independently substituted with —O—, —S—, —NH—, —N(CH 3 )—, —CO—, —COO—, —OCO—, —OCOO—, —SCO—, —COS—, or —C≡C—, in a state where oxygen atoms are not directly bonded to each other. A1, A2, A3, A4, and A5 each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a 1,4-cyclohexenyl group, a tetrahydropyran-2,5-diyl group, a 1,3-dioxane-2,5-diyl group, a tetrahydrothiopyran-2,5-diyl group, a 1,4-bicyclo (2,2,2) octylene group, a decahydronaphthalene-2,6-diyl group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a pyrazine-2,5-diyl group, a thiophene-2,5-diyl group-, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a 2,6-naphthylene group, a phenanthrene-2,7-diyl group, a 9,10-dihydrophenanthrene-2,7-diyl group, a 1,2,3,4,4a,9,10a-octahydrophenanthrene-2,7-diyl group, a 1,4-naphthylene group, a benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl group, a benzo[1,2-b:4,5-b′]diselenophene-2,6-diyl group, a [1]benzothieno[3,2-b]thiophene-2,7-diyl group, a [1]benzoselenopheno[3,2-b]selenophene-2,7-diyl group, or a fluorene-2, 7-diyl group. n, 1, k each independently represent 0 or 1, a relationship of 0<n+1+k<3 is satisfied. Z0, Z1, Z2, Z3, Z4, Z5, and Z6 each independently represent —COO—, —OCO—, —CH 2 CH 2 —, —OCH 2 —, —CH 2 O—, —CH═CH—, —C≡C—, —CH═CHCOO—, —OCOCH═CH—, —CH 2 CH 2 COO—, —CH 2 CH 2 OCO—, —COOCH 2 CH 2 —, —OCOCH 2 CH 2 —, —CONH—, —NHCO—, an alkyl group having 2 to 10 carbon atoms which may include a halogen atom, or a single bond. n5 and m5 each independently represent 0 or 1, R 3a and R 3b represent a hydrogen atom, a halogen atom, a cyano group, or an alkyl group having 1 to 18 carbon atoms, the alkyl group may be substituted with one or more of halogen atoms or CN, and one CH 2 group or two or more of (—CH 2 —)'s that are not adjacent to each other present in this group may be each mutually independently substituted with —O—, —S—, —NH—, —N(CH 3 )—, —CO—, —COO—, —OCO—, —OCOO—, —SCO—, —COS—, or —C≡C—, in a state where oxygen atoms are not directly bonded to each other. Alternatively, R 3a and R 3b preferably represent General Formula (3-a).
[Chem. 232]
—P 3a (3-a)
(In the formula, R 3a represents a polymerizable functional group and SP 3a represents the same meaning as SP 1 .)
P 3a preferably represents a substituent selected from a polymerizable group represented by Formula (P-1) to Formula (P-20).
Among these polymerizable functional groups, from a viewpoint of increasing polymerizability and storage stability, Formula (P-1), (P-2), (P-7), (P-12), or (P-13) is preferable, and Formula (P-1), (P-7), or (P-12) is more preferable.
As specific examples of the polymerizable chiral compound, compounds of Compounds (3-5) to (3-25) can be used, but there is no limitation to the following compounds.
In the formulae, m, n, k, and l each independently represent an integer of 1 to 18, and R 1 to R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a carboxyl group, or a cyano group. In a case where these groups are an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, all of the groups may be unsubstituted or substituted with one halogen atom or two or more of halogen atoms.
(Polymerizable Discotic Compound)
The polymerizable liquid crystal composition of the present invention can also include a polymerizable discotic compound which may exhibit liquid crystal properties or may be amorphous, in addition to the polymerizable compound represented by General Formula (II).
The polymerizable discotic compound used in the present invention preferably includes one or more of polymerizable functional groups. Examples of such a compound include a polymerizable compound disclosed in JP-A-H7-281028, JP-A-H7-287120, JP-A-H7-333431, and JP-A-H8-27284.
It is necessary that a blending amount of the polymerizable discotic compound is suitably adjusted in accordance with the compound, and the blending amount is preferably 0% to 10% by mass in the polymerizable liquid crystal composition.
As one example of General Formula of the polymerizable discotic compound, General Formulae (4-1) to (4-3) can be used, but there is no limitation to the general formulae.
In the formulae, SP 4 represents an alkylene group having 0 to 18 carbon atoms, the alkylene group may be substituted with one or more of halogen atoms, a CN group, or an alkyl group having 1 to 8 carbon atoms including a polymerizable functional group, and one CH 2 group or two or more of (—CH 2 —)'s that are not adjacent to each other present in this group may be each mutually independently substituted with —O—, —S—, —NH—, —N(CH 3 )—, —CO—, —COO—, —OCO—, —OCOO—, —SCO—, —COS—, or —C≡C—, in a state where oxygen atoms are not directly bonded to each other. A 4 represents a 1,4-phenylene group, a 1,4-cyclohexylene group, a 1,4-cyclohexenyl group, a tetrahydropyran-2,5-diyl group, a 1,3-dioxane-2,5-diyl group, a tetrahydrothiopyran-2,5-diyl group, a 1,4-bicyclo (2,2,2) octylene group, a decahydronaphthalene-2,6-diyl group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a pyrazine-2,5-diyl group, a thiophene-2,5-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a 2,6-naphthylene group, a phenanthrene-2,7-diyl group, a 9,10-dihydrophenanthrene-2,7-diyl group, a 1,2,3,4,4a,9,10a-octahydrophenanthrene-2,7-diyl group, a 1,4-naphthylene group, a benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl group, a benzo[1,2-b:4,5-b′]diselenophene-2,6-diyl group, a [1]benzothieno[3,2-b]thiophene-2,7-diyl group, a [1]benzoselenopheno[3,2-b]selenophene-2,7-diyl group, or a fluorene-2,7-diyl group. n5 represents 0 or 1, Z 4 a represents —CO—, —CH 2 CH 2 —, —CH 2 O—, —CH═CH—, —CH═CHCOO—, —CH 2 CH 2 COO—, —CH 2 CH 2 OCO—, —COCH 2 CH 2 —, an alkyl group having 2 to 10 carbon atoms which may include a halogen atom, or a single bond. Z 4b represents —COO—, —OCO—, —OCH 2 —, —CH 2 O—, —CH═CH—, —C≡C—, —CH═CHCOO—, —OCOCH═CH—, —CH 2 CH 2 COO—, —CH 2 CH 2 OCO—, —COOCH 2 CH 2 —, —OCOCH 2 CH 2 —, —CONH—, —NHCO—, —OCOO—, an alkyl group having 2 to 10 carbon atoms which may include a halogen atom, or a single bond. R 4 represents a hydrogen atom, a halogen atom, a cyano group, or an alkyl group having 1 to 18 carbon atoms, the alkyl group may be substituted with one or more of halogen atoms or CN, and one CH 2 group or two or more of (—CH 2 —)'s that are not adjacent to each other present in this group may be each mutually independently substituted with —O—, —S—, —NH—, —N(CH 3 )—, —CO—, —COO—, —OCO—, —OCOO—, —SCO—, —COS—, or —C≡C—, in a state where oxygen atoms are not directly bonded to each other. Alternatively, R 4 preferably represents General Formula (4-a).
[Chem. 239]
—P 4a (4-a)
(In the formula, P 4a represents a polymerizable functional group and SP 3a represents the same meaning as Sp 1 .)
P 4a preferably represents a substituent selected from a polymerizable group represented by Formula (P-1) to Formula (P-20).
Among these polymerizable functional groups, from a viewpoint of increasing polymerizability and storage stability, Formula (P-1), (P-2), (P-7), (P-12), or (P-13) is preferable, and Formula (P-1), (P-7), or (P-12) is more preferable.
As specific examples of the polymerizable discotic compound, compounds of Compounds (4-4) to (4-8) can be used, but there is no limitation to the following compounds.
In the formulae, n represents an integer of 1 to 18.
(Organic Solvent)
An organic solvent may be added to the polymerizable liquid crystal composition of the present invention. The organic solvent used is not particularly limited, and is preferably an organic solvent in which the polymerizable liquid crystal compound exhibits excellent solubility, and preferably an organic solvent which can be dried at a temperature equal to or lower than 100° C. Examples of such a solvent include aromatic hydrocarbon such as toluene, xylene, cumene, or mesitylene, an ester-based solvent such as methyl acetate, ethyl acetate, propyl acetate, or butyl acetate, a ketone-based solvent such as methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, or cyclopentanone, an ether-based solvent such as tetrahydrofuran, 1,2-dimethoxy ethane, or anisole, an amide-based solvent such as N,N-dimethylformamide or N-methyl-2-pyrrolidone, propylene glycol monomethyl ether acetate, diethylene glycol monomethyl ether acetate, γ-butyrolactone, and chlorobenzene. These can be used alone or in combination of two or more kinds thereof, and it is preferable to use any one or more kinds from a ketone-based solvent, an ether-based solvent, an ester-based solvent, and an aromatic hydrocarbon-based solvent from a viewpoint of solution stability.
When the organic solvent is used as a solution, the composition used in the present invention can be applied to a substrate. A percentage of the organic solvent used in the polymerizable liquid crystal composition is not particularly limited, as long as it does not significantly damage the coated state, and the total amount of the organic solvent included in the polymerizable liquid crystal composition is preferably 10% to 95% by mass, more preferably 12% to 90% by mass, and particularly preferably 15% to 85% by mass.
When dissolving the polymerizable liquid crystal composition in the organic solvent, it is preferable to perform heating and stirring, in order to evenly dissolve the polymerizable liquid crystal composition. A heating temperature at the time of the heating and stirring may be suitably adjusted, by considering solubility of the composition used in the organic solvent, and is preferably 15° C. to 110C, more preferably 15° C. to 105° C., even more preferably 15° C. to 100° C., and particularly preferably 20° C. to 90° C., from a viewpoint of productivity.
In addition, when adding a solvent, it is preferable that stirring and mixing are performed by a dispersing stirrer. Specifically, as the dispersing stirrer, a disper, a propeller, a dispersing device including a stirring blade such as turbine blade, a paint shaker, a planetary stirring device, a shaker, or a rotary evaporator can be used. In addition, an ultrasonic irradiation device can be used.
A stirring rotation rate when adding a solvent is preferably suitably adjusted by a stirring device used, and the stirring rotation rate is preferably 10 rpm to 1,000 rpm, more preferably 50 rpm to 800 rpm, and particularly preferably 150 rpm to 600 rpm, in order to obtain an even polymerizable liquid crystal composition solvent.
(Polymerization Inhibitor)
A polymerization inhibitor is preferably added to the polymerizable liquid crystal composition of the present invention. Examples of the polymerization inhibitor include a phenol-based compound, a quinone-based compound, an amine-based compound, a thioether-based compound, and a nitroso compound.
Examples of the phenol-based compound include p-methoxyphenol, cresol, t-butylcatechol, 3.5-di-t-butyl-4-hydroxytoluene, 2.2′-methylene bis(4-methyl-6-t-butylphenol), 2.2′-methylene bis(4-ethyl-6-t-butylphenol), 4.4′-thio bis(3-methyl-6-t-butylphenol), 4-methoxy-1-naphthol, and 4,4′-dialkoxy-2,2′-bi-1-naphthol.
Examples of quinone-based compound include hydroquinone, methylhydroquinone, tert-butylhydroquinone, p-benzoquinone, methyl-p-benzoquinone, tert-butyl-p-benzoquinone, 2,5-diphenylbenzoquinone, 2-hydroxy-1,4-naphthoquinone, 1,4-naphthoquinone, 2,3-dichloro-1,4-naphthoquinone, anthraquinone, and diphenoquinone.
Examples of the amine-based compound include p-phenylenediamine, 4-aminodiphenylamine, N.N′-diphenyl-p-phenylenediamine, N-i-propyl-N′-phenyl-p-phenylenediamine, N-(1.3-dimethylbutyl)-N′-phenyl-p-phenylenediamine, N.N′-di-2-naphthyl-p-phenylenediamine, diphenylamine, N-phenyl-β-naphthylamine, 4.4′-dicumyl-diphenylamine, and 4.4′-dioctyl-diphenylamine.
Examples of the thioether-based compound include phenothiazine and distearyl thiodipropionate.
Examples of the nitroso compound include N-nitrosodiphenylamine, N-nitrosophenylnaphthylamine, N-nitrosodinaphthylamine, p-nitrosophenol, nitrosobenzene, p-nitrosodiphenylamine, α-nitroso-β-naphthols, N,N-dimethyl p-nitrosoaniline, p-nitrosodiphenylamine, p-nitrone dimethylamine, p-nitrone-N, N-diethylamine, N-nitrosoethanolamine, N-nitrosodi-n-butylamine, N-nitroso-N-n-butyl-4-butanolamine, N-nitroso-diisopropanolamine, N-nitroso-N-ethyl-4-butanolamine, 5-nitroso-8-hydroxyquinoline, N-nitrosomorpholine, N-nitroso N-phenylhydroxylamine ammonium salt, nitrosobenzene, 2,4,6-tri-tert-butylnitrone benzene, N-nitroso-N-methyl-p-toluenesulfonamide, N-nitroso-N-ethylurethane, N-nitroso-N-n-propylurethane, 1-nitroso-2-naphthol, 2-nitroso-l-naphthol, sodium 1-nitroso-2-naphthol-3,6-sulfonate, sodium 2-nitroso-l-naphthol-4-sulfonate, 2-nitroso-5-methylaminophenol hydrochloride, and 2-nitroso-5-methylaminophenol hydrochloride.
The amount of the polymerization inhibitor added is preferably 0.01% to 1.0% by mass and more preferably 0.05% to 0.5% by mass with respect to the polymerizable liquid crystal composition.
(Antioxidant)
In order to increase stability of the polymerizable liquid crystal composition of the present invention, it is preferable to add an antioxidant. Examples of such compounds include a hydroquinone derivative, a nitrosamine-based polymerization inhibitor, and a hindered phenol-based antioxidant, and more specific examples thereof include tert-butylhydroquinone, methylhydroquinone, “Q-1300” and “Q-1301” manufactured by Wako Pure Chemical Industries, Ltd., “IRGANOX1010”, “IRGANOX1035”, “IRGANOX1076”, “IRGANOX1098”, “IRGANOX1135”, “IRGANOX1330”, “IRGANOX1425”, “IRGANOX1520”, “IRGANOX1726”, “IRGANOX245”, “IRGANOX259”, “IRGANOX3114”, “IRGANOX3790”, “IRGANOX5057”, or “IRGANOX565” manufactured by BASF.
The amount of the antioxidant added is preferably 0.01% to 2.0% by mass and more preferably 0.05% to 1.0% by mass with respect to the polymerizable liquid crystal composition.
(Photopolymerization Initiator)
The polymerizable liquid crystal composition of the present invention preferably includes a photopolymerization initiator. It is preferable that at least one or more kinds of the photopolymerization initiator are included. Specific examples thereof include “Irgacure 651”, “Irgacure 184”, “Irgacure 907”, “Irgacure 127”, “Irgacure 369”, “Irgacure 379”, “Irgacure 819”, “Irgacure 2959”, “Irgacure 1800”, “Irgacure 250”, “Irgacure 754”, “Irgacure 784”, “Irgacure OXE01”, “Irgacure OXE02”, “Lucirin TPO”, “Darocur 1173”, “Darocur MBF” manufactured by BASF, “Esacure 1001M”, “Esacure KIP150”, “Speedcure BEM”, “Speedcure BMS”, “Speedcure MBP”, “Speedcure PBZ”, “Speedcure ITX”, “Speedcure DETX”, “Speedcure EBD”, “Speedcure MBB”, “Speedcure BP” manufactured by LAMBSON, “KAYACURE DMBI” by Nippon Kayaku Co., Ltd., “TAZ-A” manufactured by DKSH, “ADEKA OPTOMER SP-152”, “ADEKA OPTOMER SP-170”, “ADEKA OPTOMER N-1414”, “ADEKA OPTOMER N-1606”, “ADEKA OPTOMER N-1717”, and “ADEKA OPTOMER N-1919” manufactured by ADEKA Corporation.
The amount of the photopolymerization initiator used is preferably 0.1% to 10% by mass and particularly preferably 0.5% to 7% by mass with respect to the polymerizable liquid crystal composition. These can be used alone or in combination of two or more kinds thereof, and a sensitizer or the like may be added thereto.
(Thermal Polymerization Initiator)
In the polymerizable liquid crystal composition of the present invention, a thermal polymerization initiator may be used in combination with the photopolymerization initiator. Specific examples thereof include “V-40” and “VF-096” manufactured by Wako Pure Chemical Industries, Ltd., and “PERHEXYL D” and “PERHEXYL I” manufactured by NOF Corporation.
The amount of thermal polymerization initiator used is preferably 0.1% to 10% by mass and particularly preferably 0.5% to 5% by mass with respect to the polymerizable liquid crystal composition. These can be used alone or in combination of two or more kinds thereof.
(Surfactant)
The polymerizable liquid crystal composition of the present invention may include at least one or more kinds of surfactants, in order to decrease unevenness of film thickness, in a case where an optically anisotropic body is prepared. Examples of surfactant which can be included include alkyl carboxylate, alkyl phosphate, alkyl sulfonate, fluoroalkyl carboxylate, fluoroalkyl phosphate, fluoroalkyl sulfonate, a polyoxyethylene derivative, a fluoroalkyl ethylene oxide derivative, a polyethylene glycol derivative, an alkyl ammonium salt, and a fluoroalkyl ammonium salt, and a fluorosurfactant is particularly preferable.
Specific examples thereof include “MEGAFACE F-251”, MEGAFACE F-444”, “MEGAFACE F-477”, “MEGAFACE F-510”, “MEGAFACE F-552”, “MEGAFACE F-553”, “MEGAFACE F-554”, “MEGAFACE F-555”, “MEGAFACE F-556”, “MEGAFACE F-557” “MEGAFACE F-558”, “MEGAFACE F-559”, “MEGAFACE F-560”, “MEGAFACE F-561”, “MEGAFACE F-562”, “MEGAFACE F-563”, “MEGAFACE F-565”, “MEGAFACE F-567”, “MEGAFACE F-568”, “MEGAFACE F-569”, “MEGAFACE F-570”, “MEGAFACE F-571”, “MEGAFACE R-40”, “MEGAFACE R-41”, “MEGAFACE R43”, “MEGAFACE R94”, “MEGAFACE RS-72-K”, “MEGAFACE RS-75”, “MEGAFACE RS-76-E”, “MEGAFACE RS-90” (all manufactured by DIC Corporation), “FTERGENT 100”, “FTERGENT 100C”, “FTERGENT 110”, “FTERGENT 150”, “FTERGENT 150CH”, “FTERGENT A”, “FTERGENT 100A-K”, “FTERGENT 501”, “FTERGENT 300”, “FTERGENT 310”, “FTERGENT 320”, “FTERGENT 400SW”, “FTX-400P”, “FTERGENT 251”, “FTERGENT 215M”, “FTERGENT 212MH”, “FTERGENT 250”, “FTERGENT 222F”, “FTERGENT 212D”, “FTX-218”, “FTX-209F”, “FTX-213F”, “FTX-233F”, “FTERGENT 245F”, “FTX-208G”, “FTX-240G”, “FTX-206D”, “FTX-220D”, “FTX-230D”, “FTX-240D”, “FTX-207S”, “FTX-211S”, “FTX-220S”, “FTX-230S”, “FTX-750FM”, “FTX-730FM”, “FTX-730FL”, “FTX-710FS”, “FTX-710FM”, “FTX-710FL”, “FTX-750LL”, “FTX-730LS”, “FTX-730LM”, “FTX-730LL”, “FTX-710LL” (all manufactured by Neos Company Limited), “BYK-300”, “BYK-302”, “BYK-306”, “BYK-307”, “BYK-310”, “BYK-315”, “BYK-320”, “BYK-322”, “BYK-323”, “BYK-325”, “BYK-330”, “BYK-331”, “BYK-333”, “BYK-337”, “BYK-340”, “BYK-344”, “BYK-3440”, “BYK-370”, “BYK-375”, “BYK-377”, “BYK-350”, “BYK-352”, “BYK-354”, “BYK-355”, “BYK-356”, “BYK-358N”, “BYK-361N”, “BYK-357”, “BYK-390”, “BYK-392”, “BYK-UV3500”, “BYK-UV3510”, “BYK-UV3570”, “BYK-Silclean3700” (all manufactured by BYK), “TEGO Rad2100”, “TEGO Rad2200N”, “TEGO Rad2250”, “TEGO Rad2300”, “TEGO Rad2500”, “TEGO Rad2600”, “TEGO Rad2700” (all manufactured by TOMOE Engineering Co., Ltd.), “N215”, “N535”, “N605K”, and “N935” (all manufactured by Solvay).
The amount of surfactant used is preferably 0.01% to 2% by mass and particularly preferably 0.05% to 0.5% by mass with respect to the polymerizable liquid crystal composition.
In addition, by using the surfactant, in a case where an optically anisotropic body is obtained by using the polymerizable liquid crystal composition of the invention, it is possible to effectively decrease the tilt angle of the air interface and by suitably selecting the surfactant, it is also possible to control the tilt angle.
In the polymerizable liquid crystal composition of the present invention, a compound including a repeating unit represented by General Formula (7) and having a weight average molecular weight equal to or greater than 100 is used, as a compound other than the surfactant exhibiting an effect of effectively decreasing the tilt angle of the air interface, in a case where an optically anisotropic body is obtained.
[Chem. 244]
CR 11 R 12 —CR 13 R 14 (7)
In the formula, R 11 , R 12 , R 13 , and R 14 each independently represent a hydrogen atom, a halogen atom, or a hydrocarbon group having 1 to 20 carbon atoms, and hydrogen atoms in the hydrocarbon group may be substituted with one or more of halogen atoms.
Examples of a suitable compound represented by General Formula (7) include polyethylene, polypropylene, polyisobutylene, paraffin, liquid paraffin, chlorinated polypropylene, chlorinated paraffin, and chlorinated liquid paraffin.
The amount of the compound represented by General Formula (7) added is preferably 0.01% to 1% by mass and more preferably 0.05% to 0.5% by mass with respect to the polymerizable liquid crystal composition.
(Curing Agent)
In the polymerizable liquid crystal composition of the present invention, a curing agent may be used. Specific examples thereof include aliphatic polyamine such as diethylenetriamine or triethylenetetramine, EH-235R-2 manufactured by ADEKA Corporation, and a ketimine compound such as jERCURE H3, H30 manufactured by Mitsubishi Chemical Corporation.
The amount of curing agent used is preferably 0.01% to 20% by mass, more preferably 0.05% to 15% by mass, and particularly preferably 0.1% to 10% by mass, with respect to the polymerizable liquid crystal composition. These can be used alone or in combination of two or more kinds thereof.
(Other Additives)
In addition, for adjusting physical properties, if necessary, additives such as amorphous polymerizable compound, a thixotropic agent, an ultraviolet absorber, an infrared absorber, an antioxidant, or a surface treatment agent can be added to some extent that alignment of liquid crystals is not significantly decreased.
(Manufacturing Method of Optically Anisotropic Body)
(Optically Anisotropic Body)
The optically anisotropic body of the present invention prepared by using the polymerizable liquid crystal composition of the present invention is a component obtained by laminating a base material, an alignment film, if necessary, and a polymer of the polymerizable liquid crystal composition, in this order.
(Base Material)
The base material used in the optically anisotropic body of the present invention is a base material which is generally used in a liquid crystal device, a display, an optical component, or an optical film, and is not particularly limited, as long as it is a material having heat resistance so as to withstand the heating at the time of drying after applying the polymerizable liquid crystal composition of the present invention. As the base material, an organic material such as a glass base material, a metal base material, a ceramic base material, or a plastic base material is used. Particularly, in a case where the base material is an organic material, examples thereof include a cellulose derivative, polyolefin, polyester, polycarbonate, polyacrylate (acrylic resin), polyarylate, polyether sulfone, polyimide, polyphenylene sulfide, polyphenylene ether, nylon, and polystyrene. Among these, a plastic base material such as polyester, polystyrene, polyacrylate, polyolefin, a cellulose derivative, polyarylate, or polycarbonate is preferable, and a base material such as polyacrylate, polyolefin, or a cellulose derivative is more preferable. It is particularly preferable that a cycloolefin polymer (COP) is used as polyolefin, triacetyl cellulose (TAC) is used as a cellulose derivative, and polymethyl methacrylate (PMMA) is used as polyacrylate. The shape of the base material may have a curved surface, in addition to a flat plate. These base materials may include an electrode layer and has an antireflection function or reflection function, if necessary.
The surface treatment of these base materials may be performed, in order to improve coating properties or adhesiveness of the polymerizable liquid crystal composition of the present invention. As the surface treatment, ozone treatment, plasma treatment, corona treatment, silane coupling treatment, and the like are used. In addition, in order to adjust transmittance or reflectance of light, an organic thin film, an inorganic oxide thin film, or a metal thin film may be provided on the surface of the base material by vapor deposition, or in order to provide an optically added value, the base material may be a pickup lens, a rod lens, an optical disk, a retardation film, a light diffusing film, or a color filter. Among these, a pickup lens, a retardation film, a light diffusing film, and a color filter are preferable so as to further increase the added value.
(Alignment Treatment)
The base material is generally subjected to alignment treatment or an aligned film may be provided thereon, in order to allow the polymerizable liquid crystal composition to be aligned when the polymerizable liquid crystal composition of the present invention is applied and dried. Examples of the alignment treatment include stretching treatment, rubbing treatment, polarized light ultraviolet-visible light irradiation treatment, and ion beam treatment. In a case of using an aligned film, a commonly used well-known aligned film is used. Examples of such an aligned film include compounds such as polyimide, polysiloxane, polyamide, polyvinyl alcohol, polycarbonate, polystyrene, polyphenylene ether, polyarylate, polyethylene terephthalate, polyether sulfone, an epoxy resin, an epoxyacrylate resin, an acrylic resin, a coumarin compound, a chalcone compound, a cinnamate compound, a fulgide compound, an anthraquinone compound, an azo compound, and an arylethene compound. As a compound to be subjected to the alignment treatment by rubbing, it is preferable to use a compound in which crystallization of the material is promoted by the alignment treatment or by adding a heating step after the alignment treatment. Among compounds to be subjected to the alignment treatment other than the rubbing, it is preferable to use a photo-alignment material.
(Coating)
Examples of the coating method for obtaining the optically anisotropic body of the present invention include well-known commonly used methods such as an applicator method, a bar coating method, a spin-coating method, a roll coating method, a direct gravure coating method, a reverse gravure coating method, a flexographic coating method, an ink jet method, a die coating method, a cap coating method, a dip coating method, and a slit coating method. The polymerizable liquid crystal composition is coated and then dried, if necessary.
(Polymerization Step)
The polymerization treatment of the polymerizable liquid crystal composition of the present invention, is generally performed by light irradiation such as ultraviolet light or heating in a state where the liquid crystal compounds in the polymerizable liquid crystal composition are subjected to horizontal alignment, vertical alignment, or hybrid alignment, or cholesteric alignment (plane alignment) with respect to the base material. In a case of performing the polymerization by light irradiation, specifically, it is preferable to emit ultraviolet light having a wavelength equal to or smaller than 390 nm and it is most preferable to emit light having a wavelength of 250 to 370 nm. However, in a case where the polymerizable liquid crystal composition causes decomposition or the like due to the ultraviolet light having a wavelength equal to or smaller than 390 nm, the polymerizable treatment may be preferably performed with ultraviolet light having a wavelength equal to or greater than 390 nm. This light is preferably diffuse light and unpolarized light.
(Polymerization Method)
A method of emitting active energy rays or a thermal polymerization method is used as a method of polymerizing the polymerizable liquid crystal composition of the present invention, but the method of emitting active energy rays is preferable, because the reaction proceeds at room temperature without the necessities of the heating, and among the methods, a method of emitting light such as ultraviolet rays is preferable, from a viewpoint of a simple operation.
It is preferable that a temperature at the time of emission is set as a temperature at which the polymerizable liquid crystal composition of the present invention can maintain the liquid crystal phase and is equal to or lower than 30° C. as possible, in order to avoid evocation of the thermal polymerization of the polymerizable liquid crystal composition. The liquid crystal composition generally shows liquid crystal phases at a C(solid phase)-N(nematic) transition temperature (hereinafter, abbreviated as a C—N transition temperature) to the N—I transition temperature in the heating process. Meanwhile, in the cooling process, the liquid crystal state may be maintained even at a temperature equal to or lower than the C—N transition temperature, without performing solidification, in order to acquire a thermodynamically nonequilibrium state. This state is called a supercooled state. In the present invention, the liquid crystal composition in the supercooled state is also included as the liquid crystal composition maintaining the liquid crystal phase. Specifically, it is preferable to emit ultraviolet light having a wavelength equal to or smaller than 390 nm and it is most preferable to emit light having a wavelength of 250 to 370 nm. However, in a case where the polymerizable composition causes decomposition or the like due to the ultraviolet light having a wavelength equal to or smaller than 390 nm, the polymerizable treatment may be preferably performed with ultraviolet light having a wavelength equal to or greater than 390 nm. This light is preferably diffuse light and unpolarized light. Ultraviolet light irradiation intensity is preferably 0.05 kW/m 2 to 10 kW/m 2 . The ultraviolet light irradiation intensity is particularly preferably 0.2 kW/m 2 to 2 kW/m 2 . When the ultraviolet light intensity is less than 0.05 kW/m 2 , a considerable time is taken for completing the polymerization. Meanwhile, in a case of the intensity exceeding 2 kW/m 2 , photolysis of the liquid crystal molecules in the polymerizable liquid crystal composition tends to occur, or the temperature during the polymerization may be increased due to generation of a considerable amount of heat of polymerization, an order parameter of the polymerizable liquid crystals may change, and the disorder may occur in the retardation of the polymerized film.
When a specific portion is only polymerized by the ultraviolet light irradiation using a mask, then, the alignment state of the unpolymerized portion is changed by applying an electric filed, a magnetic field, or a temperature, and then, the unpolymerized portion is polymerized, it is possible to obtain an optically anisotropic body having a plurality of regions having different alignment directions.
In addition, it is also possible to obtain an optically anisotropic body having a plurality of regions having different alignment directions, by regulating the alignment by applying an electric filed, a magnetic field, or a temperature to the polymerizable liquid crystal composition in the unpolymerized state in advance, when polymerizing only the specific portion by the ultraviolet light irradiation using a mask, and then, performing the polymerization by emitting light to the mask while maintaining the state described above.
The optically anisotropic body obtained by polymerizing the polymerizable liquid crystal composition of the present invention can be used as a single body of the optically anisotropic body by being separated from the substrate or can be used as the optically anisotropic body as it is without being peeled from the substrate. Particularly, it is useful to use the optically anisotropic body as a laminated substrate or use the optically anisotropic body by bonding the optically anisotropic body to another substrate, because the optically anisotropic body hardly contaminates other members.
(Retardation Film)
The retardation film of the present invention is manufactured in the same manner as in a case of the optically anisotropic body of the present invention. In a case where the polymerizable compound represented by General Formula (1) in the polymerizable composition is polymerized in a planar aligned state, a retardation film having birefringence in the plane with respect to the base material is obtained. The retardation film can be used as a homogeneous liquid crystal film. In a case where the polymerizable compound represented by General Formula (1) in the polymerizable composition and the polymerizable chiral compound are polymerized in a planar aligned state, a retardation film having birefringence to the outside of the plane with respect to the base material is obtained. In a case where the polymerizable compound represented by General Formula (1) in the polymerizable composition including the polymerizable discotic compound is polymerized in a planar aligned state, a retardation film having birefringence in the plane and to the outside of the plane with respect to the base material is obtained.
In addition, in a case where the base material includes the retardation film, a retardation film having birefringence obtained by adding the birefringence of the base material and the birefringence of the retardation of the film of the present invention is obtained. In the retardation film, the birefringence of the base material and the birefringence of the retardation of the film may be in the same direction or different directions in the plane of the base material. This is applied in a suitable state for the usage, in accordance with the usage of a liquid crystal device, a display, an optical element, an optical part, a colorant, a security marking, a member for laser emission, an optical film, and a compensation film.
(Phase Difference Patterning Film)
A phase difference patterning film of the present invention is a component obtained by laminating a base material, an alignment film, and a polymer of the polymerizable composition solution, in this order, in the same manner as in a case of the optically anisotropic body of the present invention. In the polymerization step, patterning is performed so as to have partially different phase difference. The patterning may be applied in different directions by linear patterning, lattice patterning, circular patterning, or polygonal patterning. This is applied, in accordance with the usage of a liquid crystal device, a display, an optical element, an optical part, a colorant, a security marking, a member for laser emission, an optical film, and a compensation film.
In a method of obtaining partially different phase difference, an alignment film is provided on a base material, and the alignment treatment is performed so that the polymerizable composition is subjected to patterning alignment, when the polymerizable composition solution of the present invention is applied and dried. As such alignment treatment, fine rubbing treatment, polarized ultraviolet visible light irradiation treatment through a photomask, or fine shape machining treatment is used. As the alignment film, a commonly used well-known oriented film is used. Examples of such an oriented film include compounds such as polyimide, polysiloxane, polyamide, polyvinyl alcohol, polycarbonate, polystyrene, polyphenylene ether, polyarylate, polyethylene terephthalate, polyether sulfone, an epoxy resin, an epoxyacrylate resin, an acrylic resin, a coumarin compound, a chalcone compound, a cinnamate compound, a fulgide compound, an anthraquinone compound, an azo compound, and an arylethene compound. As a compound to be subjected to the alignment treatment by fine rubbing, it is preferable to use a compound in which crystallization of the material is promoted by the alignment treatment or by adding a heating step after the alignment treatment. Among compounds to be subjected to the alignment treatment other than the rubbing, it is preferable to use a photo-alignment material.
EXAMPLES
Hereinafter, the present invention will be described with reference to synthesis examples, examples, and comparative example, but the present invention is not limited thereto. Unless otherwise noted, “part” and “%” are based on mass.
(Preparation of Polymerizable Composition and Manufacturing of Film)
The compound represented by General Formula (I), the compound represented by General Formula (II), Irgacure 907 (manufactured by BASF) as the photopolymerization initiator, methylhydroquinone (MEHQ) as the polymerization inhibitor, liquid paraffin (manufactured by Kanto Kagaku), or R-08 (manufactured by DIC Corporation) as the surfactant, and cyclopentanone (manufactured by Zeon Corporation) or toluene (manufactured by Kanto Kagaku) as the solvent, shown in Tables 1 to 4, were mixed at a ratio shown in the tables, and heated to 80° C. and stirred, and accordingly, uniform polymerizable compositions (coating solutions) used in Example 1 to Example 94 and Comparative Example 1 to Comparative Example 4 were obtained. The coating solution was applied onto a polyimide-attached glass substrate subjected to the rubbing treatment, so that a phase difference at 550 nm becomes 138±5 nm by using a spin coater or an applicator, and dried at 80° C. to 120° C. for 5 minutes. Then, ultraviolet light was irradiated in a nitrogen atmosphere or in the air so that UVA is 600 mJ/cm 2 , and a λ/4 retardation plate having reverse dispersibility was obtained (Example 1 to Example 94). The λ/4 retardation plate and a polarizing plate were bonded to each other so that an angle formed by a slow axis of the retardation plate and an absorption axis of the polarizing plate is 45 degrees, and a wide-band circularly polarizing plate was obtained (Example 1 to Example 94 and Comparative Example 1 to Comparative Example 4).
In addition, in the examples and the comparative examples, compounds used as the compound represented by General Formula (I) and the compound represented by General Formula (II) are the following compounds.
(Evaluation)
(Storage Stability)
Regarding the storage stability, the coating solution obtained as described above was left for 24 hours by observing the coating solution at every 5° C. from 30° C., and the lowest temperature at which crystal was not precipitated was recorded.
(Tilt Angle)
Regarding the tilt angle of the air interface, incident angle dependence of the phase difference of the obtained retardation plate was measured by using a phase difference measurement device RET-100 (manufactured by Otsuka Electronics Co., Ltd.), and the obtained measurement result was analyzed by using computer simulation software LCD-Master (manufactured by Shintech, Inc.).
(Glance)
Regarding glance, GALAXY SII mounted with an organic EL panel manufactured by SAMSUNG was disassembled, a circularly polarizing plate was peeled off and the wide-band circularly polarizing plate described above was bonded thereto, and black coloring observed from the front or an angle of 450 diagonally was evaluated based on the following criteria.
A: Coloring of reflected light is not substantially recognized. (Allowed)
B: Coloring of reflected light is extremely slightly recognized, but there are no practical problems (Allowed)
C: Coloring of reflected light is slightly recognized, but there are no practical problems (Allowed)
D: Coloring of reflected light is recognized and can be allowed according to the purpose (Allowed)
E: Coloring of reflected light is strongly recognized and cannot be allowed.
TABLE 1
Others
Evaluation
General Formula (I)
General Formula (II)
MEHQ
Irgacure
Liquid
Cyclopentanone
Storage
Tilt
Compound
(%)
Compound
(%)
(%)
907 (%)
paraffin (%)
(%)
stability (° C)
(degree)
Glance
Example 1
A11-1
15.2
G1-3
3.7
0.05
1
0.05
80
20
0
B
Example 2
A11-1
15.2
G1-4
3.7
0.05
1
0.05
80
20
1
B
Example 3
A11-1
15.2
G1-5
3.7
0.05
1
0.05
80
20
4
D
Example 4
A11-1
15.2
G3-2
3.7
0.05
1
0.05
80
20
2
A
Example 5
A11-1
15.2
G3-3
3.7
0.05
1
0.05
80
20
3
A
Example 6
A11-2
15.2
G1-2
3.7
0.05
1
0.05
80
20
2
A
Example 7
A11-2
15.2
G1-5
3.7
0.05
1
0.05
80
20
4
D
Example 8
A11-2
15.2
G2-1
3.7
0.05
1
0.05
80
20
0
B
Example 9
A11-2
15.2
G4-1
3.7
0.05
1
0.05
80
20
3
A
Example 10
A12-1
15.2
G1-5
3.7
0.05
1
0.05
80
20
4
C
Example 11
A12-1
15.2
G2-3
3.7
0.05
1
0.05
80
20
0
A
Example 12
A12-1
15.2
G2-4
3.7
0.05
1
0.05
80
20
1
A
Example 13
A12-1
15.2
G4-3
3.7
0.05
1
0.05
80
20
1
A
Example 14
A12-2
15.2
G1-1
3.7
0.05
1
0.05
80
20
1
A
Example 15
A12-2
15.2
G1-3
3.7
0.05
1
0.05
80
20
0
B
Example 16
A12-2
15.2
G2-4
3.7
0.05
1
0.05
80
20
1
A
Example 17
A12-2
15.2
G3-2
3.7
0.05
1
0.05
80
20
3
B
Example 18
A12-2
15.2
G4-3
3.7
0.05
1
0.05
80
20
1
B
Example 19
A12-3
15.2
G1-4
3.7
0.05
1
0.05
80
20
2
B
Example 20
A12-3
15.2
G4-2
3.7
0.05
1
0.05
80
20
3
A
Example 21
A12-4
15.2
G1-3
3.7
0.05
1
0.05
80
15
0
B
Example 22
A12-4
15.2
G1-5
3.7
0.05
1
0.05
80
15
4
D
Example 23
A12-4
15.2
G2-2
3.7
0.05
1
0.05
80
15
0
A
Example 24
A12-4
15.2
G2-5
3.7
0.05
1
0.05
80
15
1
A
Example 25
A12-4
15.2
G4-4
3.7
0.05
1
0.05
80
15
3
B
Example 26
A12-5
15.2
G1-4
3.7
0.05
1
0.05
80
20
2
C
TABLE 2
Others
Evaluation
General Formula (I)
General Formula (II)
MEHQ
Irgacure
Liquid
Cyclopentanone
Storage
Tilt
Compound
(%)
Compound
(%)
(%)
907 (%)
paraffin (%)
(%)
stability (° C)
(degree)
Glance
Example 27
A12-5
15.2
G2-8
3.7
0.05
1
0.05
80
20
3
A
Example 28
A12-5
15.2
G3-1
3.7
0.05
1
0.05
80
20
3
B
Example 29
A12-5
15.2
G3-4
3.7
0.05
1
0.05
80
20
9
D
Example 30
A13-1
15.2
G1-1
3.7
0.05
1
0.05
80
15
1
A
Example 31
A13-1
15.2
G1-3
3.7
0.05
1
0.05
80
15
0
B
Example 32
A13-1
15.2
G2-6
3.7
0.05
1
0.05
80
15
1
A
Example 33
A13-1
15.2
G4-2
3.7
0.05
1
0.05
80
15
3
A
Example 34
A13-1
15.2
G4-3
3.7
0.05
1
0.05
80
15
3
A
Example 35
A13-2
15.2
G1-2
3.7
0.05
1
0.05
80
20
1
A
Example 36
A13-2
15.2
G2-9
3.7
0.05
1
0.05
80
20
0
A
Example 37
A13-2
15.2
G3-3
3.7
0.05
1
0.05
80
20
1
B
Example 38
A13-3
15.2
G1-3
3.7
0.05
1
0.05
80
10
0
B
Example 39
A13-3
15.2
G1-4
3.7
0.05
1
0.05
80
10
2
B
Example 40
A13-3
15.2
G3-1
3.7
0.05
1
0.05
80
10
3
A
Example 41
A13-3
15.2
G4-5
3.7
0.05
1
0.05
80
10
3
A
Example 42
A14-1
15.2
G1-1
3.7
0.05
1
0.05
80
10
1
A
Example 43
A14-1
15.2
G1-3
3.7
0.05
1
0.05
80
10
0
B
Example 44
A14-1
15.2
G1-5
3.7
0.05
1
0.05
80
10
4
D
Example 45
A14-1
15.2
G2-9
3.7
0.05
1
0.05
80
10
0
A
Example 46
A14-1
15.2
G3-3
3.7
0.05
1
0.05
80
10
1
A
Example 47
A14-1
15.2
G4-1
3.7
0.05
1
0.05
80
10
3
A
Example 48
A14-1
15.2
G4-3
3.7
0.05
1
0.05
80
10
1
A
Example 49
A14-2
15.2
G1-3
3.7
0.05
1
0.05
80
15
0
B
Example 50
A14-2
15.2
G2-2
3.7
0.05
1
0.05
80
15
0
A
Example 51
A14-2
15.2
G2-10
3.7
0.05
1
0.05
80
15
0
A
Example 52
A14-2
15.2
G3-2
3.7
0.05
1
0.05
80
15
3
A
TABLE 3
Others
Evaluation
General Formula (I)
General Formula (II)
MEHQ
Irgacure
Liquid
Cyclopentanone
Storage
Tilt
Compound
(%)
Compound
(%)
(%)
907 (%)
paraffin (%)
(%)
stability (° C)
(degree)
Glance
Example 53
A14-2
15.2
G4-5
3.7
0.05
1
0.05
80
15
3
A
Example 54
A14-3
15.2
G1-4
3.7
0.05
1
0.05
80
15
2
B
Example 55
A14-3
15.2
G1-5
3.7
0.05
1
0.05
80
15
4
D
Example 56
A14-3
15.2
G2-8
3.7
0.05
1
0.05
80
15
3
A
Example 57
A14-3
15.2
G3-3
3.7
0.05
1
0.05
80
15
1
A
Example 58
A14-3
15.2
G4-2
3.7
0.05
1
0.05
80
15
3
A
Example 59
A15-1
15.2
G1-2
3.7
0.05
1
0.05
80
20
1
A
Example 60
A15-1
15.2
G1-3
3.7
0.05
1
0.05
80
20
0
B
Example 61
A15-1
15.2
G3-3
3.7
0.05
1
0.05
80
20
1
A
Example 62
A15-2
15.2
G1-1
3.7
0.05
1
0.05
80
20
1
A
Example 63
A15-2
15.2
G3-3
3.7
0.05
1
0.05
80
20
1
A
Example 64
A15-2
15.2
G4-4
3.7
0.05
1
0.05
80
20
3
A
Example 65
A15-3
15.2
G2-1
3.7
0.05
1
0.05
80
20
0
A
Example 66
A15-3
15.2
G3-4
3.7
0.05
1
0.05
80
20
8
D
Example 67
A15-3
15.2
G4-3
3.7
0.05
1
0.05
80
20
0
A
Example 68
A2-1
15.2
G1-1
3.7
0.05
1
0.05
80
25
1
B
Example 69
A2-1
15.2
G3-4
3.7
0.05
1
0.05
80
25
9
D
Example 70
A2-1
15.2
G4-3
3.7
0.05
1
0.05
80
25
1
A
Example 71
A2-2
15.2
G1-3
3.7
0.05
1
0.05
80
25
0
C
Example 72
A2-2
15.2
G4-3
3.7
0.05
1
0.05
80
25
0
A
Example 73
A2-3
15.2
G1-2
3.7
0.05
1
0.05
80
25
1
A
Example 74
A2-4
15.2
G1-2
3.7
0.05
1
0.05
80
25
0
A
Example 75
A2-5
15.2
G1-2
3.7
0.05
1
0.05
80
15
1
A
Example 76
A3-1
15.2
G1-5
3.7
0.05
1
0.05
80
25
4
D
Example 77
A3-1
15.2
G4-3
3.7
0.05
1
0.05
80
25
0
A
Example 78
B11-1
15.2
G1-3
3.7
0.05
1
0.05
80
15
6
C
TABLE 4
Others
Evaluation
General Formula (I)
General Formula (II)
MEHQ
Irgacure
Liquid
Cyclopentanone
Storage
Tilt
Compound
(%)
Compound
(%)
(%)
907 (%)
paraffin (%)
(%)
stability (° C)
(degree)
Glance
Example 79
B11-1
15.2
G1-5
3.7
0.05
1
0.05
80
15
3
C
Example 80
B11-1
15.2
G4-3
3.7
0.05
1
0.05
80
15
1
A
Example 81
B11-2
15.2
G4-3
3.7
0.05
1
0.05
80
10
1
A
Example 82
B11-7
15.2
G1-1
3.7
0.05
1
0.05
80
10
0
A
Example 83
B11-7
15.2
G1-5
3.7
0.05
1
0.05
80
10
3
C
Example 84
B11-8
15.2
G2-4
3.7
0.05
1
0.05
80
15
0
A
Example 85
B3-1
15.2
G4-3
3.7
0.05
1
0.05
80
15
1
A
Example 86
C11-1
15.2
G1-3
3.7
0.05
1
0.05
80
15
2
B
Example 87
C11-2
15.2
G1-3
3.7
0.05
1
0.05
80
15
1
B
Example 88
C11-5
15.2
G1-3
3.7
0.05
1
0.05
80
20
2
B
Example 89
C11-6
15.2
G1-3
3.7
0.05
1
0.05
80
15
2
B
Example 90
C11-9
15.2
G1-3
3.7
0.05
1
0.05
80
20
1
C
Example 91
C12-1
15.2
G4-3
3.7
0.05
1
0.05
80
15
1
A
Example 92
C12-3
15.2
G4-3
3.7
0.05
1
0.05
80
15
1
A
Example 93
C2-1
15.2
G1-3
3.7
0.05
1
0.05
80
20
1
B
Example 94
C3-1
15.2
G1-3
3.7
0.05
1
0.05
80
20
2
B
Comparative
G1-3
9.4
G1-6
9.5
0.05
1
0.05
80
15
2
E
Example 1
Comparative
G1-5
15
G1-6
3.9
0.05
1
0.05
80
15
3
E
Example 2
Comparative
G1-5
15.2
G3-4
3.7
0.05
1
0.05
80
10
13
E
Example 3
Comparative
G2-2
15.2
G2-8
3.7
0.05
1
0.05
80
30
1
E
Example 4
TABLE 5
Others
Evaluation
General Formula (I)
General Formula (II)
MEHQ
Irgacure
Liquid
Cyclopentanone
Storage
Tilt
Glance
Compound
(%)
Compound
(%)
(%)
907 (%)
paraffin (%)
(%)
stability (° C)
(degree)
Front
Example 95
A12-16
15.2
G1-3
3.7
0.05
1
0.05
80
5
0
A
Example 96
A12-17
15.2
G1-3
3.7
0.05
1
0.05
80
5
0
A
Example 97
A12-18
15.2
G1-3
3.7
0.05
1
0.05
80
0
0
A
Example 98
A141-1
15.2
G1-3
3.7
0.05
1
0.05
80
0
2
A
Example 99
A141-2
15.2
G1-3
3.7
0.05
1
0.05
80
0
1
A
Example 100
A141-3
15.2
G1-3
3.7
0.05
1
0.05
80
0
1
A
Example 101
A141-4
15.2
G1-3
3.7
0.05
1
0.05
80
0
1
A
Example 102
A141-5
15.2
G1-3
3.7
0.05
1
0.05
80
0
1
A
Example 103
A141-6
15.2
G1-3
3.7
0.05
1
0.05
80
0
2
A
Example 104
A141-7
15.2
G1-3
3.7
0.05
1
0.05
80
0
2
A
Example 105
A141-8
15.2
G1-3
3.7
0.05
1
0.05
80
0
1
A
Example 106
A141-9
15.2
G1-3
3.7
0.05
1
0.05
80
0
2
A
Example 107
A141-10
15.2
G1-3
3.7
0.05
1
0.05
80
0
1
A
Example 108
A141-11
15.2
G1-3
3.7
0.05
1
0.05
80
0
1
A
Example 109
A141-12
15.2
G1-3
3.7
0.05
1
0.05
80
0
1
A
Example 110
A141-13
15.2
G1-3
3.7
0.05
1
0.05
80
0
1
A
Example 111
A141-14
15.2
G1-3
3.7
0.05
1
0.05
80
0
2
A
Example 112
A141-15
15.2
G1-3
3.7
0.05
1
0.05
80
0
2
A
Example 113
A141-16
15.2
G1-3
3.7
0.05
1
0.05
80
0
2
A
Example 114
A141-17
15.2
G1-3
3.7
0.05
1
0.05
80
0
2
A
TABLE 6
Others
Evaluation
General Formula (I)
General Formula (II)
MEHQ
Irgacure
Liquid
Cyclopentanone
Storage
Tilt
Glance
Compound
(%)
Compound
(%)
(%)
907 (%)
paraffin (%)
(%)
stability (° C)
(degree)
Front
Example 115
A141-18
15.2
G1-3
3.7
0.05
1
0.05
80
0
2
A
Example 116
A141-19
15.2
G1-3
3.7
0.05
1
0.05
80
0
2
A
Example 117
A141-20
15.2
G1-3
3.7
0.05
1
0.05
80
0
2
A
Example 118
A141-21
15.2
G1-3
3.7
0.05
1
0.05
80
0
1
A
Example 119
A141-22
15.2
G1-3
3.7
0.05
1
0.05
80
0
0
A
Example 120
A141-23
15.2
G1-3
3.7
0.05
1
0.05
80
0
0
A
Example 121
A141-24
15.2
G1-3
3.7
0.05
1
0.05
80
0
0
A
Example 122
A141-25
15.2
G1-3
3.7
0.05
1
0.05
80
0
0
A
Example 123
A141-26
15.2
G1-3
3.7
0.05
1
0.05
80
0
0
A
Example 124
A141-27
15.2
G1-3
3.7
0.05
1
0.05
80
0
0
A
Example 125
A141-28
15.2
G1-3
3.7
0.05
1
0.05
80
0
0
A
Example 126
A141-29
15.2
G1-3
3.7
0.05
1
0.05
80
0
0
A
Example 127
A141-30
15.2
G1-3
3.7
0.05
1
0.05
80
0
0
A
Example 128
A141-31
15.2
G1-3
3.7
0.05
1
0.05
80
0
0
A
Example 129
A141-32
15.2
G1-3
3.7
0.05
1
0.05
80
0
0
A
Example 130
A141-33
15.2
G1-3
3.7
0.05
1
0.05
80
0
0
A
Example 131
A142-1
15.2
G1-3
3.7
0.05
1
0.05
80
0
1
A
Example 132
A142-2
15.2
G1-3
3.7
0.05
1
0.05
80
−5
1
A
Example 133
A142-3
15.2
G1-3
3.7
0.05
1
0.05
80
−5
1
A
Example 134
A142-4
15.2
G1-3
3.7
0.05
1
0.05
80
−5
1
A
TABLE 7
Others
Evaluation
General Formula (I)
General Formula (II)
MEHQ
Irgacure
Liquid
Cyclopentanone
Storage
Tilt
Glance
Compound
(%)
Compound
(%)
(%)
907 (%)
paraffin (%)
(%)
stability (° C)
(degree)
Front
Example 135
A142-5
15.2
G1-3
3.7
0.05
1
0.05
80
−5
1
A
Example 136
A142-6
15.2
G1-3
3.7
0.05
1
0.05
80
−5
1
A
Example 137
A142-7
15.2
G1-3
3.7
0.05
1
0.05
80
−5
1
A
Example 138
A142-8
15.2
G1-3
3.7
0.05
1
0.05
80
−5
1
A
Example 139
A142-9
15.2
G1-3
3.7
0.05
1
0.05
80
−5
1
A
Example 140
A142-10
15.2
G1-3
3.7
0.05
1
0.05
80
−5
0
A
Example 141
A142-11
15.2
G1-3
3.7
0.05
1
0.05
80
−5
0
A
Example 142
A142-12
15.2
G1-3
3.7
0.05
1
0.05
80
−5
0
A
Example 143
A142-13
15.2
G1-3
3.7
0.05
1
0.05
80
−5
0
A
Example 144
A142-14
15.2
G1-3
3.7
0.05
1
0.05
80
−5
0
A
Example 145
A142-15
15.2
G1-3
3.7
0.05
1
0.05
80
−5
0
A
Example 146
A143-1
15.2
G1-3
3.7
0.05
1
0.05
80
−5
0
A
Example 147
A143-2
15.2
G1-3
3.7
0.05
1
0.05
80
−5
0
A
Example 148
A144-1
15.2
G1-3
3.7
0.05
1
0.05
80
0
0
A
TABLE 8
Others
Cyclo-
Evaluation
General Formula (I)
General Formula (II)
MEHQ
Irgacure
Liquid
pentanone
Storage
Tilt
Glance
Glance
Compound
(%)
Compound
(%)
(%)
907 (%)
paraffin (%)
(%)
stability (° C)
(degree)
Front
45°
Example 149
A11-1
15.2
G3-5
3.7
0.05
1
0.02
80
30
65
A
B
Example 150
A11-1
15.2
G4-3
3.7
0.05
1
0.02
80
30
60
A
B
Example 151
A11-1
15.2
G1-6
3.7
0.05
1
0.02
80
30
3
B
D
Example 152
A11-1
15.2
G3-4
3.7
0.05
1
0.02
80
30
9
C
D
Example 153
A11-2
15.2
G3-5
3.7
0.05
1
0.02
80
30
60
A
B
Example 154
A11-2
15.2
G3-2
3.7
0.05
1
0.02
80
30
55
A
B
Example 155
A11-2
15.2
G1-2
3.7
0.05
1
0.02
80
30
3
A
C
Example 156
A11-3
15.2
G4-3
3.7
0.05
1
0.02
80
30
65
A
B
Example 157
A11-3
15.2
G1-6
3.7
0.05
1
0.02
80
30
4
B
D
Example 158
A11-3
15.2
G3-4
3.7
0.05
1
0.02
80
30
8
C
D
Example 159
A12-1
15.2
G3-5
3.7
0.05
1
0.02
80
30
60
A
B
Example 160
A12-1
15.2
G4-3
3.7
0.05
1
0.02
80
30
60
A
B
Example 161
A12-1
15.2
G1-6
3.7
0.05
1
0.02
80
30
2
A
C
Example 162
A12-1
15.2
G3-4
3.7
0.05
1
0.02
80
30
9
C
D
Example 163
A12-2
15.2
G3-5
3.7
0.05
1
0.02
80
30
60
A
B
Example 164
A12-2
15.2
G1-2
3.7
0.05
1
0.02
80
30
2
A
C
Example 165
A12-3
15.2
G3-5
3.7
0.05
1
0.02
80
30
65
A
B
Example 166
A12-3
15.2
G4-3
3.7
0.05
1
0.02
80
30
60
A
B
Example 167
A12-3
15.2
G1-6
3.7
0.05
1
0.02
80
30
2
A
C
Example 168
A12-16
15.2
G3-5
3.7
0.05
1
0.02
80
20
60
A
B
TABLE 9
Others
Cyclo-
Evaluation
General Formula (I)
General Formula (II)
MEHQ
Irgacure
Liquid
pentanone
Storage
Tilt
Glance
Glance
Compound
(%)
Compound
(%)
(%)
907 (%)
paraffin (%)
(%)
stability (° C)
(degree)
Front
45°
Example 169
A12-16
15.2
G4-3
3.7
0.05
1
0.02
80
20
55
A
B
Example 170
A12-16
15.2
G1-6
3.7
0.05
1
0.02
80
20
4
A
C
Example 171
A12-16
15.2
G3-4
3.7
0.05
1
0.02
80
20
8
C
D
Example 172
A12-17
15.2
G3-5
3.7
0.05
1
0.02
80
20
65
A
B
Example 173
A12-17
15.2
G3-2
3.7
0.05
1
0.02
80
20
60
A
B
Example 174
A12-17
15.2
G1-2
3.7
0.05
1
0.02
80
20
2
A
C
Example 175
A12-18
15.2
G3-5
3.7
0.05
1
0.02
80
10
65
A
B
Example 176
A12-18
15.2
G4-3
3.7
0.05
1
0.02
80
10
60
A
B
Example 177
A12-18
15.2
G1-6
3.7
0.05
1
0.02
80
10
3
A
C
Example 178
A13-1
15.2
G3-5
3.7
0.05
1
0.02
80
25
60
A
B
Example 179
A13-1
15.2
G1-6
3.7
0.05
1
0.02
80
25
1
A
C
Example 180
A13-1
15.2
G3-4
3.7
0.05
1
0.02
80
25
8
C
D
Example 181
A13-2
15.2
G3-5
3.7
0.05
1
0.02
80
25
60
A
B
Example 182
A13-2
15.2
G4-3
3.7
0.05
1
0.02
80
25
55
A
B
Example 183
A13-2
15.2
G1-2
3.7
0.05
1
0.02
80
25
2
A
C
Example 184
A13-3
15.2
G3-5
3.7
0.05
1
0.02
80
25
60
A
B
Example 185
A13-3
15.2
G1-6
3.7
0.05
1
0.02
80
25
1
B
D
Example 186
A141-22
15.2
G3-5
3.7
0.05
1
0.02
80
10
70
A
A
Example 187
A141-22
15.2
G4-3
3.7
0.05
1
0.02
80
10
65
A
A
Example 188
A141-22
15.2
G1-6
3.7
0.05
1
0.02
80
10
1
A
C
TABLE 10
Others
Cyclo-
Evaluation
General Formula (I)
General Formula (II)
MEHQ
Irgacure
Liquid
pentanone
Storage
Tilt
Glance
Glance
Compound
(%)
Compound
(%)
(%)
907 (%)
paraffin (%)
(%)
stability (° C)
(degree)
Front
45°
Example 189
A141-22
15.2
G3-4
3.7
0.05
1
0.02
80
10
5
C
D
Example 190
A141-23
15.2
G3-5
3.7
0.05
1
0.02
80
10
70
A
A
Example 191
A141-23
15.2
G3-2
3.7
0.05
1
0.02
80
10
65
A
A
Example 192
A141-23
15.2
G1-6
3.7
0.05
1
0.02
80
10
2
A
C
Example 193
A141-24
15.2
G3-5
3.7
0.05
1
0.02
80
10
65
A
A
Example 194
A141-24
15.2
G4-3
3.7
0.05
1
0.02
80
10
65
A
A
Example 195
A141-24
15.2
G1-2
3.7
0.05
1
0.02
80
10
3
A
C
Example 196
A141-24
15.2
G3-4
3.7
0.05
1
0.02
80
10
5
C
D
Example 197
A141-25
15.2
G3-5
3.7
0.05
1
0.02
80
10
65
A
A
Example 198
A141-25
15.2
G3-2
3.7
0.05
1
0.02
80
10
65
A
A
Example 199
A141-25
15.2
G1-6
3.7
0.05
1
0.02
80
10
1
A
C
Example 200
A141-26
15.2
G3-5
3.7
0.05
1
0.02
80
10
65
A
A
Example 201
A141-26
15.2
G4-3
3.7
0.05
1
0.02
80
10
65
A
A
Example 202
A141-26
15.2
G1-6
3.7
0.05
1
0.02
80
10
4
A
C
Example 203
A141-27
15.2
G3-5
3.7
0.05
1
0.02
80
10
65
A
A
Example 204
A141-27
15.2
G3-2
3.7
0.05
1
0.02
80
10
65
A
A
Example 205
A141-27
15.2
G1-2
3.7
0.05
1
0.02
80
10
2
A
C
Example 206
A141-28
15.2
G3-5
3.7
0.05
1
0.02
80
10
65
A
A
Example 207
A141-28
15.2
G4-3
3.7
0.05
1
0.02
80
10
65
A
A
Example 208
A141-28
15.2
G1-6
3.7
0.05
1
0.02
80
10
3
A
C
TABLE 11
Others
Cyclo-
Evaluation
General Formula (I)
General Formula (II)
MEHQ
Irgacure
Liquid
pentanone
Storage
Tilt
Glance
Glance
Compound
(%)
Compound
(%)
(%)
907 (%)
paraffin (%)
(%)
stability (° C)
(degree)
Front
45°
Example 209
A141-29
15.2
G3-5
3.7
0.05
1
0.02
80
10
70
A
A
Example 210
A141-29
15.2
G4-3
3.7
0.05
1
0.02
80
10
70
A
A
Example 211
A141-29
15.2
G1-6
3.7
0.05
1
0.02
80
10
1
A
C
Example 212
A141-30
15.2
G3-5
3.7
0.05
1
0.02
80
10
70
A
A
Example 213
A141-30
15.2
G3-2
3.7
0.05
1
0.02
80
10
65
A
A
Example 214
A141-30
15.2
G1-2
3.7
0.05
1
0.02
80
10
2
A
C
Example 215
A141-31
15.2
G3-5
3.7
0.05
1
0.02
80
10
70
A
A
Example 216
A141-31
15.2
G4-3
3.7
0.05
1
0.02
80
10
65
A
A
Example 217
A141-31
15.2
G1-6
3.7
0.05
1
0.02
80
10
1
A
C
Example 218
A141-32
15.2
G3-5
3.7
0.05
1
0.02
80
10
70
A
A
Example 219
A141-32
15.2
G4-3
3.7
0.05
1
0.02
80
10
70
A
A
Example 220
A141-32
15.2
G1-2
3.7
0.05
1
0.02
80
10
2
A
C
Example 221
A141-33
15.2
G3-5
3.7
0.05
1
0.02
80
10
70
A
A
Example 222
A141-33
15.2
G3-2
3.7
0.05
1
0.02
80
10
65
A
A
Example 223
A141-33
15.2
G1-6
3.7
0.05
1
0.02
80
10
1
A
C
Example 224
A141-33
15.2
G3-4
3.7
0.05
1
0.02
80
10
4
C
D
Example 225
A142-10
15.2
G3-5
3.7
0.05
1
0.02
80
5
70
A
A
Example 226
A142-10
15.2
G3-2
3.7
0.05
1
0.02
80
5
65
A
A
Example 227
A142-10
15.2
G1-2
3.7
0.05
1
0.02
80
5
3
A
C
Example 228
A142-10
15.2
G3-4
3.7
0.05
1
0.02
80
5
6
C
D
TABLE 12
Others
Cyclo-
Evaluation
General Formula (I)
General Formula (II)
MEHQ
Irgacure
Liquid
pentanone
Storage
Tilt
Glance
Glance
Compound
(%)
Compound
(%)
(%)
907 (%)
paraffin (%)
(%)
stability (° C)
(degree)
Front
45°
Example 229
A142-11
15.2
G3-5
3.7
0.05
1
0.02
80
5
70
A
A
Example 230
A142-11
15.2
G4-3
3.7
0.05
1
0.02
80
5
65
A
A
Example 231
A142-11
15.2
G1-6
3.7
0.05
1
0.02
80
5
1
A
C
Example 232
A142-12
15.2
G3-5
3.7
0.05
1
0.02
80
5
65
A
A
Example 233
A142-12
15.2
G4-3
3.7
0.05
1
0.02
80
5
65
A
A
Example 234
A142-12
15.2
G1-2
3.7
0.05
1
0.02
80
5
1
A
C
Example 235
A142-13
15.2
G3-5
3.7
0.05
1
0.02
80
5
70
A
A
Example 236
A142-13
15.2
G3-2
3.7
0.05
1
0.02
80
5
65
A
A
Example 237
A142-13
15.2
G1-6
3.7
0.05
1
0.02
80
5
2
A
C
Example 238
A142-13
15.2
G3-4
3.7
0.05
1
0.02
80
5
6
C
D
Example 239
A142-14
15.2
G3-5
3.7
0.05
1
0.02
80
0
70
A
A
Example 240
A142-14
15.2
G4-3
3.7
0.05
1
0.02
80
0
70
A
A
Example 241
A142-14
15.2
G1-6
3.7
0.05
1
0.02
80
0
2
A
C
Example 242
A142-14
15.2
G3-4
3.7
0.05
1
0.02
80
0
5
C
D
Example 243
A142-15
15.2
G3-5
3.7
0.05
1
0.02
80
0
70
A
A
Example 244
A142-15
15.2
G3-2
3.7
0.05
1
0.02
80
0
65
A
A
Example 245
A142-15
15.2
G1-2
3.7
0.05
1
0.02
80
0
1
A
C
Example 246
A143-1
15.2
G3-5
3.7
0.05
1
0.02
80
0
70
A
A
Example 247
A143-1
15.2
G4-3
3.7
0.05
1
0.02
80
0
70
A
A
Example 248
A143-1
15.2
G1-6
3.7
0.05
1
0.02
80
0
2
A
C
TABLE 13
Others
Cyclo-
Evaluation
General Formula (I)
General Formula (II)
MEHQ
Irgacure
Liquid
pentanone
Storage
Tilt
Glance
Glance
Compound
(%)
Compound
(%)
(%)
907 (%)
paraffin (%)
(%)
stability (° C)
(degree)
Front
45°
Example 249
A143-1
15.2
G3-4
3.7
0.05
1
0.02
80
0
5
C
D
Example 250
A143-2
15.2
G3-5
3.7
0.05
1
0.02
80
0
70
A
A
Example 251
A143-2
15.2
G3-2
3.7
0.05
1
0.02
80
0
65
A
A
Example 252
A143-2
15.2
G1-2
3.7
0.05
1
0.02
80
0
1
A
C
Example 253
A143-2
15.2
G3-4
3.7
0.05
1
0.02
80
0
5
C
D
Comparative
G1-3
9.4
G2-1
9.5
0.05
1
0.02
80
25
2
E
E
Example 5
Comparative
G1-5
15
G2-1
3.9
0.05
1
0.02
80
20
2
E
E
Example 6
Comparative
G1-6
15.2
G3-5
3.7
0.05
1
0.02
80
0
70
E
E
Example 7
Comparative
G2-3
15.2
G4-3
3.7
0.05
1
0.02
80
15
60
E
E
Example 8
From the results described above, it is found that the compositions of the examples have excellent glance, compared to the compositions of the comparative examples.
1.PublishNumber: US-2018037817-A1
2.Date Publish: 20180208
3.Inventor: KUWANA YASUHIRO
HORIGUCHI MASAHIRO
ISHII TORU
NOSE SAYAKA
KOISO AKIHIRO
4.Inventor Harmonized: KUWANA YASUHIRO(JP)
HORIGUCHI MASAHIRO(JP)
ISHII TORU(JP)
NOSE SAYAKA(JP)
KOISO AKIHIRO(JP)
5.Country: US
6.Claims:
(en)The polymerizable composition prevents precipitation and the like of crystals and has high storage stability. A polymer compound is added to the polymerizable composition. In a case where a film-shaped polymer obtained by polymerizing the polymerizable composition is prepared, a tilt angle formed with an air interface is small, and glances of reflected light when a circularly polarizing plate is obtained by combining the polymer with a polarizing plate are removed. In addition, there is provided a polymer obtained by polymerizing the polymerizable composition, and an optically anisotropic body using the polymer. The polymerizable composition includes a reverse dispersible compound represented by General Formula (I), and a compound represented by General Formula (II).
7.Description:
(en)TECHNICAL FIELD
The present invention relates to a polymerizable composition including a compound having a polymerizable group, a polymerizable liquid crystal composition, and an optically anisotropic body using the polymerizable liquid crystal composition.
BACKGROUND ART
A compound including a polymerizable group (polymerizable compound) is used in various optical materials. For example, it is possible to prepare a polymer having even alignment by arranging a polymerizable composition including the polymerizable compound in a liquid crystal state and causing polymerization. Such a polymer can be used in a polarizing plate or a retardation plate necessary for a display. In many cases, a polymerizable composition including two or more kinds of polymerizable compounds is used, in order to satisfy optical characteristics, a rate of polymerization, solubility, a melting point, a glass transition temperature, transparency of a polymer, mechanical strength, surface hardness, heat resistance, and light resistance required. At this time, it is necessary that the polymerizable compound to be used imparts excellent physical properties to the polymerizable composition without negatively affecting other characteristics.
In order to improve a viewing angle of a liquid crystal display, it is necessary that wavelength dispersibility of birefringence of a retardation film is decreased or reversed. Preferred examples of the polymerizable compound to be used for this object include a polymerizable compound which hardly causes occurrence of precipitation of crystals and has high storage stability in a case where the polymerizable compound is added to a polymerizable composition. In addition, with respect to a film-shaped polymer prepared by polymerizing the polymerizable composition containing the polymerizable compound, it is preferable that haze is slight, evenness of film thickness is high, unevenness of alignment hardly occurs, surface hardness is high, and adhesiveness is high. Further, it is preferable that a alignment angle with an air interface is small (a tilt angle is small), because phase difference characteristics of a composition can be exhibited to the maximum degree and angle dependency is also easily adjusted. Meanwhile, by controlling the tilt angle, it is also possible to improve viewing angle characteristics of a display. In a case where a retardation film is used for on-board equipment or mobile equipment, high durability with respect to ultraviolet light is required. Accordingly, in a case where the film-shaped polymer is irradiated with ultraviolet light, it is preferable that discoloration or peeling from a base material hardly occurs and alignment defects hardly occur.
In addition, as an antireflective film of an organic EL element, the use of a circularly polarizing plate prepared by combining the polymer and a polarizing plate with each other has also been investigated. In this case, it is necessary that quantity of reflected light is reduced or glances of the reflected light are removed (set to have an achromatic color) even when the reflected light slightly exists.
CITATION LIST
Patent Literature
[PTL 1] JP-A-2007-328053
SUMMARY OF INVENTION
Technical Problem
An object of the present invention is to provide a polymerizable composition having high storage stability in which precipitation of crystals or the like is prevented in a case where the polymerizable composition is added to a polymerizable composition, with respect to a film-shaped polymer obtained by polymerizing the polymerizable composition, a tilt angle formed with an air interface is small or controlled to be a suitable value, and with respect to a circularly polarizing plate prepared in combination with a polarizing plate, glances of reflected light are reduced. In addition, another object of the present invention is to provide a polymer obtained by polymerizing the polymerizable composition and an optically anisotropic body using the polymer.
Solution to Problem
As a result of intensive studies to solve the problems described above, the inventors have reached the development of a compound represented by General Formula (I). That is, according to the aspect of the present invention, there is provided a polymerizable composition including: (a) a reverse dispersible compound represented by General Formula (I):
(in the formula, R 1 , R 2 , R 3 , and R 4 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 80 carbon atoms, the group may have a substituent, one or more of arbitrary carbon atoms may be substituted with a hetero atom, W 1 and W 2 each independently represent a single bond or a group including a conjugated system including 2 to 100π electrons, M 1 and M 2 each independently represent a group including a mesogenic group, n1 and n2 each independently represent 0 or 1, provided that when n1 or n2 is 0, the corresponding group is a hydrogen atom, n3 represents an integer of 1 to 1,000, W 1 , W 2 , M 1 , and M 2 may each independently include a substituent L, L represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, or L may represent a group represented by P L —(S L —X L ) kL — where P L represents a polymerizable group, S L represents a spacer group or a single bond, in a case where a plurality of S L is present, these may be the same as each other or different from each other, X L represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of X L is present, these may be the same as each other or different from each other (provided that P L —(S L —X L ) kL — does not include a —O—O— bond), in a case where a plurality of L is present in the compound, these may be the same as each other or different from each other, and kL represents an integer of 0 to 10, and M 1 -W 1 , W 1 -M 2 , and/or M 2 -W 2 may each independently form a conjugated system),
(b) a compound represented by General Formula (II):
(in the formula, P 21 represents a polymerizable functional group, S 21 represents an alkylene group having 0 to 18 carbon atoms (hydrogen atoms in the alkylene group may be substituted with one or more halogen atoms or CN, one CH 2 group or two or more of (—CH 2 —)'s that are not adjacent to each other present in this group may be each mutually independently substituted with —O—, —COO—, —OCO—, or —OCO—O—), X 21 represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond (provided that P 21 —S 21 and S 21 —X 21 do not include a —O—O—, —O—NH—, or —O—S— group), q 1 represents 0 or 1, MG represents a mesogenic group, and R 21 represents a hydrogen atom, a halogen atom, a cyano group, or a linear or a branched alkyl group having 1 to 12 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, or a General Formula (II-a):
[Chem. 3]
—(X 22 —S 22 ) q2 —P 23 (II-a)
(in the formula, P 23 represents a reactive functional group, S 22 represents a component which is the same as that defined in the description regarding S 21 , X 22 represents a component which is the same as that defined in the description regarding X 21 (provided that P 23 —S 22 and S 22 —X 22 do not include a —O—O—, —O—NH—, or —O—S— group), and q 2 represents 0 or 1),
(c) an initiator, if necessary, and
(d) a solvent, if necessary,
a polymerizable composition including the compounds, a resin, a resin additive, oil, a filter, an adhesive, a pressure-sensitive adhesive, fat, ink, a medicine, cosmetics, a detergent, a building material, a packaging material, a liquid crystal material, an organic EL material, an organic semiconductor material, an electronic material, a display element, an electronic device, communication equipment, an automobile part, an aircraft part, a machine part, an agricultural chemical, and a food each using the compounds, products using these, a polymerizable liquid crystal composition, a polymer obtained by polymerizing the polymerizable liquid crystal composition, and an optically anisotropic body using the polymer.
Advantageous Effects of Invention
The polymerizable composition including the compounds having a specific structure of the present invention has high storage stability and is useful as a constituent member of a polymerizable composition. In addition, the optically anisotropic body using the polymerizable liquid crystal composition including the compounds of the present invention is useful for an optical material such as a retardation film, because a degree of unevenness is small, a tilt angle formed with an air interface is small or controlled to be a suitable value, glances of reflected light are reduced with respect to a circularly polarizing plate prepared in combination with a polarizing plate.
DESCRIPTION OF EMBODIMENTS
The present invention provides a polymerizable composition formed of a reverse dispersible compound represent by General Formula (I) and a compound represented by General Formula (II), a resin, a resin additive, oil, a filter, an adhesive, a pressure-sensitive adhesive, fat, ink, a medicine, cosmetics, a detergent, a building material, a packaging material, a liquid crystal material, an organic EL material, an organic semiconductor material, an electronic material, a display element, an electronic device, communication equipment, an automobile part, an aircraft part, a machine part, an agricultural chemical, and a food using the composition, products using these, a polymerizable liquid crystal composition, a polymer obtained by polymerizing the polymerizable liquid crystal composition, and an optically anisotropic body using the polymer.
In a graph in which a horizontal axis indicates a wavelength γ of light incident to a retardation film and a vertical axis indicates a birefringence Δn, in a case where the birefringence Δn decreases, as the wavelength γ decreases, the film is generally called as a film showing “reverse wavelength dispersibility” or “reverse dispersibility” by persons skilled in the art. In the present invention, a compound configuring a retardation film showing reverse dispersibility is referred to as a reverse dispersible compound.
<<General Formula (I)>>
In the present invention, a reverse dispersible compound represented by General Formula (I) is included as an essential component.
<<R 1 , R 2 , R 3 , and R 4 >>
In General Formula (I), R 1 , R 2 , R 3 , and R 4 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 80 carbon atoms, the group may have a substituent, and one or more of arbitrary carbon atoms may be substituted with a hetero atom. In addition, R 1 , R 2 , R 3 , and R 4 preferably each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, the group may have a substituent, and one or more of arbitrary carbon atoms may be substituted with a hetero atom. More specifically, R 1 , R 2 , R 3 , and R 4 each independently represent a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a cyano group, a nitro group, an isocyano group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —C═C—, or —C≡C— (one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom), or are preferably a group including a polymerizable group.
In General Formula (I), regarding R 1 , R 2 , R 3 , and R 4 , R 1 being present and at least one of R 2 , R 3 , and R 4 being present are preferably groups including a polymerizable group.
The group including a polymerizable group is preferably a group represented by General Formula (I-R).
(In the formula, P 1 represents a polymerizable group, S 1 represents a spacer group or a single bond, in a case where a plurality of S 1 is present, these may be the same as each other or different from each other, X 1 represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of X 1 is present in the compound, these may be the same as each other or different from each other (provided that P 1 —(S 1 —X 1 ) k — does not include a —O—O— bond), and k represents an integer of 0 to 10.)
In General Formula (I-R), P 1 represents a polymerizable group and preferably represents a group selected from Formula (P-1) to Formula (P-20).
These polymerizable groups are polymerized by radical polymerization, radical addition polymerization, cation polymerization, and anion polymerization. Particularly, in a case of performing ultraviolet ray polymerization as a polymerization method, Formula (P-1), Formula (P-2), Formula (P-3), Formula (P-4), Formula (P-5), Formula (P-7), Formula (P-11), Formula (P-13), Formula (P-15), or Formula (P-18) is preferable, Formula (P-1), Formula (P-2), Formula (P-7), Formula (P-11), or Formula (P-13) is more preferable, Formula (P-1), Formula (P-2), or Formula (P-3) is even more preferable, and Formula (P-1) or Formula (P-2) is particularly preferable.
In General Formula (I-R), S 1 represents a spacer group or a single bond, and in a case where a plurality of S 1 is present, these may be the same as each other or different from each other. In addition, S 1 , as a spacer group, preferably represents an alkylene group having 1 to 20 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, —OCO—, —OCO—O—, —CO—NH—, —NH—CO—, —CH═CH—, or —C≡C—. From viewpoints of availability of raw materials and ease of synthesis, in a case where a plurality of S 1 is present, these may be the same as each other or different from each other, S 1 's more preferably each independently represent an alkylene group having 1 to 10 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, or —OCO—, or a single bond, even more preferably each independently represent an alkylene group having 1 to 10 carbon atoms or a single bond. In a case where a plurality of S 1 is present, these may be the same as each other or different from each other, and S 1 's particularly preferably each independently represent an alkylene group having 1 to 8 carbon atoms.
In General Formula (I-R), X 1 represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, and in a case where a plurality of X 1 is present, these may be the same as each other or different from each other (provided that P 1 —(S 1 —X 1 ) k — does not include a —O—O— bond). From viewpoints of availability of raw materials and ease of synthesis, in a case where a plurality of X 1 is present, these may be the same as each other or different from each other, X 1 's more preferably each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond, even more preferably each independently represent —O—, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond. In a case where a plurality of X 1 is present, these may be the same as each other or different from each other, and X 1 's particularly preferably each independently represent —O—, —COO—, —OCO—, or a single bond.
In General Formula (I-R), k represents an integer of 0 to 10, preferably represents an integer of 0 to 5, more preferably represents an integer of 0 to 2, and particularly preferably represents 1.
In a case where R 1 , R 2 , R 3 , and R 4 of General Formula (I) represent a group other than the group including a polymerizable group, R 1 , R 2 , R 3 , and R 4 preferably represent a group selected from R 5 (in the formula, R 5 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom).
From viewpoints of liquid crystal properties, reverse dispersibility, ease of synthesis, and storage stability, the group represented by R 5 more preferably represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, —OCO—, —O—CO—O—, —CO—NH—, or —NH—CO— and one or more of arbitrary hydrogen atoms may be substituted with a fluorine atom, even more preferably represents a hydrogen atom, a fluorine atom, a chlorine atom, or a linear alkyl group having 1 to 10 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, —OCO—, or —O—CO—O— and one or more of arbitrary hydrogen atoms may be substituted with a fluorine atom, still more preferably represents a linear alkyl group having 1 to 10 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, and particularly preferably represents a linear alkyl group having 1 to 5 carbon atoms.
<<Substituent L>>
A compound represented by General Formula (I) may be unsubstituted or substituted with a substituent L. The substituent L represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or a branched alkyl group having 1 to 20 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, or L may represent a group represented by P L —(S L —X L ) kL — where P L represents a polymerizable group, S L represents a spacer group or a single bond, in a case where a plurality of SL is present, these may be the same as each other or different from each other, X L represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of X L is present, these may be the same as each other or different from each other (provided that P L —(S L —X L ) kL — does not include a —O—O— bond), kL represents an integer of 0 to 10, kL is preferably 1, and in a case where a plurality of L is present in the compound, these may be the same as each other or different from each other. In addition, from viewpoints of availability of raw materials and ease of synthesis, in a case where a plurality of the substituents L are present, these may be the same as each other or different from each other, and the substituent L preferably represents a fluorine atom, a chlorine atom, a nitro group, a cyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, or —OCO— and one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom. In a case where a plurality of the substituents L are present, these may be the same as each other or different from each other, and the substituent L more preferably represents a fluorine atom, a chlorine atom, a nitro group, a cyano group, or a linear alkyl group having 1 to 12 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—. In a case where a plurality of the substituents L are present, these may be the same as each other or different from each other, and the substituent L particularly preferably represents a fluorine atom, a cyano group, a methyl group, or a methoxy group.
<<W 1 and W 2 >
In General Formula (I), W 1 and W 2 each independently represent a group including a single bond or a conjugated system including 2 to 100π electrons. From viewpoints of availability of raw materials and ease of synthesis, W 1 and W 2 are preferably groups including a single bond or a carbon group or a hydrocarbon group including 2 to 80π electrons, in which one or more of arbitrary carbon atoms may be substituted with a hetero atom, and a single bond or an aromatic and/or nonaromatic hydrocarbon ring having 5 to 80 carbon atoms, which is not substituted or may be substituted with one or more of substituents L and in which one or more of arbitrary carbon atoms may be substituted with a hetero atom.
In General Formula (I), W 1 more preferably represents a group represented by General Formula (I-W1) and W 2 more preferably represents a group represented by General Formula (I-W2).
In the formula, V 1 , V 2 , V 3 , and V 4 each independently represent a single bond or a divalent linking group, B 1 , B 2 , and B 3 each independently represent a single bond or an aromatic and/or nonaromatic hydrocarbon ring having 5 to 80 carbon atoms which may be substituted, one or more of arbitrary carbon atoms of the carbon ring or the hydrocarbon ring may be substituted with a hetero atom, these groups may be unsubstituted or substituted with one or more of substituents L. In a case where B 3 represents a single bond, a hydrogen atom or a group represented by the substituent L is bonded thereto, and n4 and n5 are integers of 0 to 10.)
In the formula, V 1 , V 2 , V 3 , and V 4 preferably each independently represent a group selected from Formula (V-1) to Formula (V-15).
In the formulae, Y 1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, and in a case where a plurality of Y 1 is present, these may be the same as each other or different from each other. Alternatively, Y 1 may represent a group represented by P Y —(S Y —X Y ) j —, P Y represents a polymerizable group and preferably represents a group selected from Formula (P-1) to Formula (P-20), and the polymerizable groups are polymerized by radical polymerization, radical addition polymerization, cation polymerization, and anion polymerization. Particularly, in a case of performing ultraviolet ray polymerization as a polymerization method, Formula (P-1), Formula (P-2), Formula (P-3), Formula (P-4), Formula (P-5), Formula (P-7), Formula (P-11), Formula (P-13), Formula (P-15), or Formula (P-18) is preferable, Formula (P-1), Formula (P-2), Formula (P-7), Formula (P-11), or Formula (P-13) is more preferable, Formula (P-1), Formula (P-2), or Formula (P-3) is even more preferable, and Formula (P-1) or Formula (P-2) is particularly preferable. S Y represents a spacer group or a single bond, and in a case where a plurality of S Y is present, these may be the same as each other or different from each other. From viewpoints of liquid crystal properties, availability of raw materials, and ease of synthesis, in a case where a plurality of S Y is present, these may be the same as each other or different from each other, and S Y 's preferably each independently represent an alkylene group having 1 to 20 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF═S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, or —C≡C—. In a case where a plurality of S Y is present, these may be the same as each other or different from each other, and S Y 's more preferably each independently represent a linear alkylene group having 1 to 20 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, —OCO—, or —OCO—O—. In a case where a plurality of S Y is present, these may be the same as each other or different from each other, and S Y 's even more preferably each independently represent a linear alkylene group having 1 to 12 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—. From viewpoints of liquid crystal properties and solubility in a solvent, S Y particularly preferably represents a linear alkylene group having 1 to 12 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—. X Y represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, and in a case where a plurality of X Y is present, these may be the same as each other or different from each other (provided that P Y —(S Y —X Y ) j — does not include a —O—O— bond). From viewpoints of availability of raw materials and ease of synthesis, in a case where a plurality of X Y is present, these may be the same as each other or different from each other, X Y 's preferably each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond, more preferably each independently represent —O—, —COO—, OCO—, or a single bond, and particularly preferably represents a single bond. j represents an integer of 0 to 10, and preferably represents an integer of 1 to 3, from viewpoints of liquid crystal properties and availability of raw materials. j particularly preferably represents 1, from a viewpoint of hardening shrinkage in a case where a film is obtained.
In Formula (V-1) to Formula (V-15), in a case where the group represented by P Y —(S Y —X Y ) j — is bonded to a N atom, a group directly bonded to the N atom is preferably —CH 2 —, from a viewpoint of ease of synthesis.
In Formula (V-1) to Formula (V-15), from viewpoints of a phase difference, temporal stability of reverse wavelength dispersibility, and peeling in a case of irradiation with ultraviolet light for a long period of time, the group represented by P Y —(S Y —X Y ) j — preferably represents a group selected from Formula (PY-1), Formula (PY-2), or Formula (PY-3).
(In the formula, ja represents an integer of 2 to 20 and jb represents an integer of 1 to 6.) In the Formula (PY-1), from a viewpoint of liquid crystal properties, ja more preferably represents an integer of 2 to 12 and particularly preferably represents an integer of 2 to 8. In Formula (PY-2) and Formula (PY-3), from a viewpoint of liquid crystal properties, jb more preferably represents an integer of 1 to 3 and particularly preferably represents 1 or 2.
In Formula (V-1) to Formula (V-15), in a case where Y 1 represents a group other than the group represented by P Y —(S Y —X Y ) j —, Y 1 represents a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, and in a case where a plurality of Y 1 is present, these preferably represent groups which may be the same as each other or different from each other. In this case, from viewpoints of liquid crystal properties, availability of raw materials, and ease of synthesis, in a case where a plurality of Y 1 is present, these may be the same as each other or different from each other, and Y 1 more preferably represents a linear or branched alkyl group having 1 to 20 carbon atoms, in which one or more of arbitrary hydrogen atoms in the group may be substituted with a fluorine atom and one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —CO—, —COO—, —OCO—, —O—CO—O—, —CH═CH—, —CF═CF—, or —C≡C—. In a case where a plurality of Y 1 is present, these may be the same as each other or different from each other, and Y 1 even more preferably represents a linear alkyl group having 1 to 20 carbon atoms, in which one or more of arbitrary hydrogen atoms in the group may be substituted with a fluorine atom and one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—. In a case where a plurality of Y 1 is present, these may be the same as each other or different from each other, and Y 1 particularly preferably represents a linear alkyl group having 1 to 10 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—. In addition, from viewpoints of solubility in various solvents and adhesiveness to various base materials (or aligned films), Y 1 is preferably a group selected from a group represented by H 3 C—(O— (CH 2 ) j1 ) j2 — (in the formula, j1 represents an integer of 2 to 10, j2 represents an integer of 1 to 10, j1 is preferably an integer of 2 to 6, j2 is preferably an integer of 1 to 4, j1 is more preferably 2 or 3, j2 is more preferably an integer of 1 to 3, j1 is particularly preferably 2, and j2 is particularly preferably 2 or 3), a single bond, a double bond, —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 1 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, and —CH 2 —OCO—, provided that at least one of M 1 -V 1 , V 1 —B 1 , B 1 —V 2 , V 2 -M 2 , M 2 -V 3 , V 3 —B 2 , B 2 —V 4 , and V 4 —B 3 present in Formula (I-W1) and Formula (I-W2) forms a conjugated system.
From viewpoints of reverse dispersibility, availability of raw materials, and ease of synthesis, V 1 , V 2 , V 3 , and V 4 are more preferably each independently a group selected from the groups represented by Formula (V-1) to (V-15), a single bond, a double bond, —O—, —S—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, and —CH 2 —OCO—, even more preferably each independently a group selected from the groups represented by Formula (V-1) to (V-15), a single bond, a double bond, —S—, —CH 2 —, —COO—, —OCO—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, and —CH 2 CH 2 —, still more preferably each independently a group selected from the groups represented by Formula (V-1) to (V-15), a single bond, a double bond, —CH 2 —, —COO—, —OCO—, and —CH 2 CH 2 —, and particularly preferably each independently a group selected from the groups represented by Formula (V-1) to (V-15), a single bond, and a double bond, provided that at least one of M 1 -V 1 , V 1 —B 1 , B 1 —V 2 , V 2 -M 2 , M 2 -V 3 , V 3 —B 2 , B 1 —V 4 , and V 4 —B 3 present in Formula (I-W1) and Formula (I-W2) forms a conjugated system.
From viewpoints of availability of raw materials and ease of synthesis, in a case where Y 1 is bonded to a carbon atom, Y 1 preferably represents a hydrogen atom, a fluorine atom, a chlorine atom, a nitro group, a cyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, or —OCO— and one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, more preferably represents a hydrogen atom, a fluorine atom, a chlorine atom, a nitro group, a cyano group, or a linear alkyl group having 1 to 12 carbon atoms, even more preferably represents a hydrogen atom, a fluorine atom, a cyano group, or a linear alkyl group having 1 to 8 carbon atoms, and particularly preferably represents a hydrogen atom. In addition, in a case where Y 1 is bonded to a nitrogen atom, Y 1 preferably represents a hydrogen atom or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, OR—OCO— and one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, more preferably represents a hydrogen atom or a linear or branched alkyl group having 1 to 20 carbon atoms, even more preferably represents a hydrogen atom or a linear or branched alkyl group having 1 to 8 carbon atoms, and particularly preferably represents a hydrogen atom.
In the formulae, B 1 being present and B 2 and B 3 being present preferably each independently represent Formula (B-1) to Formula (B-21) or a single bond.
(in the formulae, in a ring structure, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. Here, the expression that a bonding site may be at an arbitrary position, means that, since B 1 is a divalent group, two bonding sites are provided at arbitrary positions, for example (hereinafter, in the present invention, the expression that a bonding site may be at an arbitrary position, indicates the same meaning). In addition, these groups may be unsubstituted or substituted with one or more of substituents L, and in a case where B 3 represents a single bond, these groups are bonded to a hydrogen atom or a group represented by the substituent L).
From viewpoints of availability of raw materials, ease of synthesis, and reverse dispersibility, B 1 , B 2 , and B 3 preferably each independently represent a group selected from Formula (B-3), Formula (B-4), Formula (B-5), Formula (B-6), Formula (B-7), Formula (B-8), Formula (B-10), Formula (B-11), Formula (B-12), Formula (B-13), Formula (B-17), Formula (B-18), Formula (B-19), Formula (B-20), Formula (B-21), or a single bond.
A group represented by Formula (B-3) preferably represents a group selected from Formula (B-3-1) to Formula (B-3-7),
(in the formulae, in a ring structure, a bonding site may be at an arbitrary position, and R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. In addition, these groups may be unsubstituted or substituted with one or more of substituents L), and more preferably represents a group selected from Formula (B-3-2), Formula (B-3-4), Formula (B-3-5), Formula (B-3-6), and Formula (B-3-7).
A group represented by Formula (B-4) preferably represents a group selected from Formula (B-4-1) to Formula (B-4-8),
(in the formulae, in a ring structure, a bonding site may be at an arbitrary position. In addition, these groups may be unsubstituted or substituted with one or more of substituents L), and more preferably represents a group represented by Formula (B-4-1).
A group represented by Formula (B-5) preferably represents a group selected from Formula (B-5-1) to Formula (B-5-6).
(In the formulae, in a ring structure, a bonding site may be at an arbitrary position, and R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.)
A group represented by Formula (B-6) preferably represents a group selected from Formula (B-6-1) to Formula (B-6-9).
(In the formulae, in a ring structure, a bonding site may be at an arbitrary position, and R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.)
A group represented by Formula (B-7) preferably represents a group selected from Formula (B-7-1) to Formula (B-7-12),
(in the formulae, in a ring structure, a bonding site may be at an arbitrary position, and R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. In addition, these groups may be unsubstituted or substituted with one or more of substituents L), and more preferably represents a group selected from Formula (B-7-8), Formula (B-7-9), Formula (B-7-10), Formula (B-7-11), and Formula (B-7-12), and even more preferably represents a group represented by Formula (B-7-11)
A group represented by Formula (B-8) preferably represents a group selected from Formula (B-8-1) to Formula (B-8-8),
(in the formulae, in a ring structure, a bonding site may be at an arbitrary position, and R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. In addition, these groups may be unsubstituted or substituted with one or more of substituents L), and more preferably represents a group selected from Formula (B-8-2), Formula (B-8-3), Formula (B-8-4), Formula (B-8-6), Formula (B-8-7), and Formula (B-8-8).
A group represented by Formula (B-10) preferably represents a group selected from Formula (B-10-1) to Formula (B-10-19).
(In the formulae, in a ring structure, a bonding site may be at an arbitrary position, and R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.)
A group represented by Formula (B-11) preferably represents a group selected from Formula (B-11-1) to Formula (B-11-7),
(in the formulae, in a ring structure, a bonding site may be at an arbitrary position, and R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. In addition, these groups may be unsubstituted or substituted with one or more of substituents L), and more preferably represents a group selected from Formula (B-11-1), Formula (B-11-2), and Formula (B-11-7).
A group represented by Formula (B-12) preferably represents a group selected from Formula (B-12-1) to Formula (B-12-4),
(in the formulae, in a ring structure, a bonding site may be at an arbitrary position, and R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. In addition, these groups may be unsubstituted or substituted with one or more of substituents L), and more preferably represents a group selected from Formula (B-12-1) and Formula (B-12-4).
A group represented by Formula (B-13) preferably represents a group selected from Formula (B-13-1) to Formula (B-13-10).
(In the formulae, in a ring structure, a bonding site may be at an arbitrary position, and R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.)
A group represented by Formula (B-17) preferably represents a group selected from Formula (B-17-1) to Formula (B-17-18).
(In the formulae, in a ring structure, a bonding site may be at an arbitrary position, and R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.)
A group represented by Formula (B-18) preferably represents a group selected from Formula (B-18-1) to Formula (B-18-4).
(In the formulae, in a ring structure, a bonding site may be at an arbitrary position, and R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.)
A group represented by Formula (B-19) preferably represents a group selected from Formula (B-19-1) to Formula (B-19-16).
(In the formulae, in a ring structure, a bonding site may be at an arbitrary position, and R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.)
A group represented by Formula (B-20) preferably represents a group selected from Formula (B-20-1) to Formula (B-20-12).
(In the formulae, in a ring structure, a bonding site may be at an arbitrary position, and R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.)
A group represented by Formula (B-21) preferably represents a group selected from Formula (B-21-1) to Formula (B-21-13).
(In the formulae, in a ring structure, a bonding site may be at an arbitrary position, and R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.)
<<M 1 and M 2 >>
In General Formula (I), M 1 and M 2 each independently represent a group including a mesogenic group.
More specifically, M 1 preferably represents a group represented by Formula (I-M1) and M 2 preferably represents a group represented by Formula (I-M2).
(In the formula, A 1 , A 2 , A 3 , and A 4 each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, these groups may be unsubstituted or substituted with one or more of substituents L, and, in a case where a plurality of each of A 1 , A 2 , A 3 , and A 4 is present, these may be the same as each other or different from each other. Z 1 , Z 2 , Z 3 , and Z 4 each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of each of Z 1 , Z 2 , Z 3 , and Z 4 is present, these may be the same as each other or different from each other. T 1 represents a trivalent group which may be substituted, in a case where n2 is 0, T 2 represents a trivalent group which may be substituted, in a case where n2 is 1, T 2 represents a tetravalent group which may be substituted, and m1, m2, m3, and m4 each independently represent an integer of 0 to 5.)
From viewpoints of availability of raw materials and ease of synthesis, A 1 , A 2 , A 3 , and A 4 preferably represent a 1,4-phenylene group, a 1,4-cyclohexylene group, or a naphthalene-2,6-diyl group which are not substituted or may be substituted with one or more substituent L, more preferably each independently represent a group selected from Formula (A-1) to Formula (A-11),
even more preferably each independently represent a group selected from Formula (A-1) to Formula (A-8), and particularly preferably each independently represent a group selected from Formula (A-1) to Formula (A-4).
From viewpoints of liquid crystal properties of the compound, availability of raw materials, and ease of synthesis, Z 1 , Z 2 , Z 3 , and Z 4 preferably each independently represent a single bond, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —CF═CF—, —C≡C—, or a single bond, more preferably each independently represent —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —C≡C—, or a single bond, even more preferably each independently represent —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond, and particularly preferably each independently represent —COO—, —OCO—, or a single bond.
m1, m2, m3, and m4 each independently represent an integer of 0 to 5, and from viewpoints of liquid crystal properties, ease of synthesis, and storage stability, m1, m2, m3, and m4 preferably each independently represent an integer of 1 to 4, more preferably each independently represent an integer of 1 to 3, and particularly preferably each independently represent 1 or 2. m1+m2 and m3+m4 preferably each independently represent an integer of 1 to 4 and particularly preferably each independently represent 2, 3, or 4.
In Formula (I-M1) and Formula (I-M2), T 1 and T 2 are preferably each independently a group selected from Formula (T-1) to Formula (T-22).
(In the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L, and k1 represents an integer of 1 to 20.)
<<n1, n2, and n3>>
n1 and n2 each independently represent 0 or 1. In a case where n1 is 0, a group linked to W 1 which will be described later represents a hydrogen atom, and in a case where n2 is 0, a group linked to M 2 which will be described later represents a hydrogen atom.
n3 represents an integer of 1 to 1,000, preferably represents an integer of 1 to 10, more preferably represents an integer of 1 to 5, even more preferably represents an integer of 1 to 3, and particularly preferably represents 1 or 2.
n1, n2, and n3 each represent the numbers described above, a case where A: <n1 and n2 represent 0 and n3 represents 1>, B: <n1 represents 1, n2 represents 0, and n3 represents 1>, C: <n1 represents 0, and n2 and n3 represent 1>, or D: <n1 and n2 represent 0 and n3 represents 2 to 1,000> is particularly preferable, because excellent reverse dispersibility is exhibited. Hereinafter, each group will be described in the aspects A: to D: which are particularly preferred aspects.
Compound in Which <<n1 and n2 Represent 0 and n3 Represents 1>>
<W 1 -A11>
In the compound in which <n1 and n2 represent 0 and n3 represents 1>, in a case of significantly considering surface hardness and appearance after ultraviolet light irradiation, when a film-shaped polymer is prepared, in General Formula (I), W 1 is preferably a group represented by Formula (I-W11).
(In the formula, V 1 and V 2 being present each independently represent a single bond or a divalent linking group, B 1 being present and B 11 each independently a group selected from Formula (B-1) to Formula (B-21),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and a single bond, and n41 represents an integer of 0 to 5.)
V 1 and V 2 are preferably each independently the groups represented by Formula (V-1) to Formula (V-15) shown in the section <<W 1 and W 2 >> (in the formulae, in a case of including Y 1 , Y 1 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis described in the section <<W 1 and W 2 >>), a single bond, a double bond, —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, more preferably a group selected from Formula (V-5), Formula (V-6), Formula (V-8), Formula (V-9), Formula (V-10), a single bond, and a double bond, and particularly preferably a single bond.
B 1 and B 11 are preferably each independently a group selected from Formula (B-3), Formula (B-4), Formula (B-8), Formula (B-13), Formula (B-16), and a single bond, and more preferably each independently a group selected from Formula (B-3), Formula (B-4), Formula (B-8), and a single bond. More specifically, B 1 and B 11 are specifically preferably each independently a group selected from Formula (B-3-1), Formula (B-3-2), Formula (B-3-5), Formula (B-3-7), Formula (B-4-1), Formula (B-8-4), Formula (B-8-7), Formula (B-13-7), Formula (B-13-8) shown in the section <<W 1 and W 1 >>, and a single bond, and specifically preferably each independently a group selected from Formula (B-3-7), Formula (B-4-1), and Formula (B-8-4).
n41 more preferably represents 0, 1, or 2, even more preferably represents 0 or 1, and still more preferably represents 1.
<W 1 -A12>
In the compound in which <n1 and n2 represent 0 and n3 represents 1>, in a case of significantly considering storage stability of a polymerizable composition, unevenness of alignment when a film-shaped polymer is prepared, and alignment defects after ultraviolet light irradiation, in General Formula (I), W 1 is preferably a group represented by Formula (I-W12).
(In the formula, V 1 and V 2 being present each independently represent a single bond or a divalent linking group, V 21 represents —NR 0 —, —CR 0 ═, ═CR 0 —, —N═, or ═N— (in the formulae, R 0 's each independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms), B 1 being present and B 11 each independently a group selected from Formula (B-1) to Formula (B-21),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and a single bond, and n41 represents an integer of 0 to 5.) V 21 more preferably represents a group selected from —NR 0 —, —N═, and ═N— (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms) and even more preferably represents —NH—.
V 1 and V 2 being present are more preferably each independently a group represented by Formula (V-1) to Formula (V-15) (in the formulae, in a case of including Y 1 , Y 1 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis described in the section <<W 1 and W 2 >>), a single bond, a double bond, —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, and —CH 2 —OCO—, even more preferably each independently Formula (V-1), Formula (V-2), Formula (V-5), Formula (V-6), Formula (V-8), Formula (V-9), a single bond, —S—, or —CH 2 CH 2 —, and still more preferably each independently Formula (V-5) or a single bond.
B 1 and B 1 are preferably each independently a group selected from Formula (B-3), Formula (B-4), Formula (B-6), Formula (B-7), Formula (B-8), Formula (B-10), Formula (B-11), Formula (B-21), and a single bond, and more preferably each independently a group selected from Formula (B-3), Formula (B-4), Formula (B-8), and Formula (B-21). More specifically, B 1 and B 11 are preferably a group selected from Formula (B-3-2), Formula (B-3-5), Formula (B-3-7), Formula (B-4-1), Formula (B-4-2), Formula (B-4-3), Formula (B-4-4), Formula (B-4-5), Formula (B-6-7), Formula (B-7-8), Formula (B-7-11), Formula (B-7-12), Formula (B-8-3), Formula (B-8-4), Formula (B-10-11), Formula (B-10-16), Formula (B-11-6), and Formula (B-21-12) shown in the section <<W 1 and W 2 >>, and more preferably a group selected from Formula (B-3-7), Formula (B-4-1), Formula (B-4-2), Formula (B-4-3), Formula (B-8-4), and Formula (B-21-12).
n41 more preferably represents 0, 1, or 2 and even more preferably represents 0 or 1.
<W 1 -A13>
In the compound in which <n1 and n2 represent 0 and n3 represents 1>, in a case of significantly considering evenness of film thickness and adhesiveness, when a film-shaped polymer is prepared, in General Formula (I), W 1 is preferably a group represented by Formula (I-W13).
(In the formula, V 1 and V 2 being present each independently represent a single bond or a divalent linking group, V 21 represents —CR 0 ═CR 0 —, —C≡C—, —CR 0 ═N—, —N═CR 0 —, —NR 0 —CR 0 ═, ═CR 0 —NR 0 —, —NR 0 —N═, ═N—NR 0 —, —N═N—, or ═N—N═ (in the formulae, R 0 's each independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms), B 1 being present and B 11 each independently a group selected from Formula (B-1) to Formula (B-21),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and a single bond, and n41 represents an integer of 0 to 5.) V 21 more preferably represents a group selected from —CR 0 ═CR 0 —, —C≡C—, —CR 0 ═N—, —N═CR 0 —, —NR 0 —CR 0 ═, ═CR 0 —NR 0 —, —N═N—, or ═N—N═ (in the formulae, R 0 's each independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms), even more preferably represents a group selected from —CH═CH—, —CH═N—, —N═CH—, and —N═N—, and still more preferably represents a group selected from —CH═CH—, —CH═N—, and —N═CH—. V 1 and V 2 are more preferably each independently a group represented by Formula (V-1) to Formula (V-15) (in the formulae, in a case of including Y 1 , Y 1 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis described in the section <<W 1 and W 2 >>), a single bond, a double bond, —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, and —CH 2 —OCO—, even more preferably each independently Formula (V-1), Formula (V-2), Formula (V-3), Formula (V-4), Formula (V-5), Formula (V-10), —CH 2 CH 2 —, or a single bond, and still more preferably each independently Formula (V-1), Formula (V-2), Formula (V-3), Formula (V-4), or a single bond. B 1 and B 11 are preferably each independently a group selected from Formula (B-3), Formula (B-4), Formula (B-5), Formula (B-6), Formula (B-7), Formula (B-8), Formula (B-10), Formula (B-1), Formula (B-12), Formula (B-13), Formula (B-17), Formula (B-18), and a single bond, and more preferably each independently a group selected from Formula (B-3), Formula (B-4), Formula (B-7), Formula (B-8), Formula (B-10), Formula (B-12), Formula (B-13), and a single bond. More specifically, B 1 and B 11 are preferably a group selected from Formula (B-3-2), Formula (B-3-5), Formula (B-4-1), Formula (B-7-11), Formula (B-8-7), Formula (B-10-11), Formula (B-12-3), Formula (B-12-4), Formula (B-13-6), and a single bond, more preferably a group selected from Formula (B-3-2), Formula (B-3-5), Formula (B-4-1), Formula (B-7-11), Formula (B-8-7), Formula (B-12-4) shown in the section <<W 1 and W 2 >>, and a single bond, and even more preferably a group selected from Formula (B-3-2), Formula (B-4-1), Formula (B-8-7), Formula (B-12-4), and a single bond.
n41 more preferably represents 0, 1, or 2, even more preferably represents 0 or 1, and still more preferably represents 1.
<W 1 -A14>
In the compound in which <n1 and n2 represent 0 and n3 represents 1>, in a case of significantly considering storage stability when the compound is added to a polymerizable composition, a haze value when a film-shaped polymer is prepared, and alignment defects after ultraviolet light irradiation, in General Formula (I), W 1 is preferably a group represented by Formula (I-W14).
(In the formula, V 1 and V 2 being present each independently represent a single bond or a divalent linking group, V 21 represents —CR 0 ═CR 0 —, —C≡C—, —CR 0 ═N—, —N═CR 0 —, —NR 0 —CR 0 ═, ═CR 0 —NR 0 —, —NR 0 —N═, ═N—NR 0 —, —N═N—, or ═N—N═, V 22 represents —NR 0 —, —CR 0 ═, ═CR 0 —, —N═, or ═N— (in the formulae, R 0 's each independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms), B 1 being present and B 11 each independently a group selected from Formula (B-1) to Formula (B-21),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and a single bond, and n41 represents an integer of 0 to 5.) V 21 more preferably represents a group selected from —CR 0 ═N—, —N═CR 0 —, —NR 0 —CR 0 ═, ═CR 0 —NR 0 —, —NR 0 —N═, ═N—NR 0 —, and ═N—N═ (in the formulae, R 0 each independently represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms), and even more preferably represents a group selected from —CH═N—, —N═CH—, —NH—CH═, ═CH—NH—, —NH—N═, ═N—NH—, and ═N—N═. V 22 more preferably represents a group selected from —NR 0 —, —N═, and ═N— (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms) and even more preferably represents a group selected from —NH—, —N═, and ═N—. V 1 and V 2 being present are more preferably each independently a group represented by Formula (V-1) to Formula (V-15) (in the formulae, in a case of including Y 1 , Y 1 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis described in the section <<W 1 and W 2 >>), a single bond, a double bond, —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, and —CH 2 —OCO—, even more preferably each independently Formula (V-5), Formula (V-6), Formula (V-8), Formula (V-9), a single bond, or —CH 2 CH 2 —, and still more preferably each independently a single bond. B 1 being present and B 11 are preferably each independently a group selected from Formula (B-3), Formula (B-4), Formula (B-7), Formula (B-8), Formula (B-10), Formula (B-11), Formula (B-12), and a single bond, and more preferably each independently a group selected from Formula (B-4), Formula (B-7), Formula (B-8), and a single bond. More specifically, B 1 being present and B 11 are preferably a group selected from Formula (B-3-1), Formula (B-3-2), Formula (B-3-5), Formula (B-3-7), Formula (B-4-1), Formula (B-4-3), Formula (B-4-6), Formula (B-7-11), Formula (B-8-4), Formula (B-8-7), Formula (B-10-11), Formula (B-11-1), Formula (B-12-4) shown in the section <<W 1 and W 1 >>, and a single bond, and more preferably a group selected from Formula (B-4-1), Formula (B-7-11), Formula (B-8-7), and a single bond.
n41 more preferably represents 0, 1, or 2, even more preferably represents 0 or 1, and still more preferably represents 0.
<W 1 -A15>
In the compound in which <n1 and n2 represent 0 and n3 represents 1>, in a case of significantly considering a haze value and evenness of film thickness, when a film-shaped polymer is prepared, in General Formula (I), W 1 is preferably a group represented by Formula (I-W18).
(In the formula, V 1 and V 2 being present each independently represent a single bond or a divalent linking group, V 21 , V 22 , V 23 , and V 24 represent —CR 0 ═CR 0 —, —C≡C—, —CR 0 ═N—, —N═CR 0 —, —NR 0 —CR 0 ═, ═CR 0 —NR 0 —, —NR 0 —N═, ═N—NR 0 —, —N═N—, ═N—N═, —NR 0 —, —CR 0 ═, ═CR 0 —, —N═, or ═N— (in the formulae, R 0 's each independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms), B 1 and B 1 being present each independently a group selected from Formula (B-1) to Formula (B-21),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and a single bond, and n41 represents an integer of 0 to 5.) V 21 , V 22 , V 23 , and V 24 preferably represent —CR 0 ═CR 0 —, —C≡C—, —CR 0 ═N—, —N═CR 0 —, —NR 0 —CR 0 ═, ═CR 0 —NR 0 —, —NR 0 —N═, ═N—NR 0 —, —NR 0 —, —CR 0 ═, ═CR 0 —, —N═, or ═N— (in the formulae, R 0 each independently represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms), more preferably represent —CR 0 ═CR 0 —, —C≡C—, —CR 0 ═N—, —N═CR 0 —, —NR 0 —N═, ═N—NR 0 —, —NR 0 —, —CR 0 ═, or ═CR 0 — (in the formulae, R 0 each independently represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms), even more preferably represent —CR 0 ═N— or —N═CR 0 — (in the formulae, R 0 each independently represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms), and still more preferably —CH═N— or —N═CH—. V 1 and V 2 being present are more preferably each independently a group represented by Formula (V-1) to Formula (V-15) (in the formulae, in a case of including Y 1 , Y 1 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis described in the section <<W 1 and W 2 >>), a single bond, a double bond, —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, and —CH 2 —OCO—, even more preferably each independently Formula (V-6), a single bond, or —CH 2 CH 2 —, and still more preferably each independently Formula (V-6) or a single bond. B 1 being present and B 11 are preferably each independently a group selected from Formula (B-3), Formula (B-4), Formula (B-7), Formula (B-8), Formula (B-10), Formula (B-11), Formula (B-12), or a single bond, and more preferably each independently a group selected from Formula (B-4), Formula (B-8), Formula (B-12), or a single bond. More specifically, B 1 being present and B 11 are preferably a group selected from Formula (B-3-2), Formula (B-3-5), Formula (B-4-1), Formula (B-7-11), Formula (B-8-7), Formula (B-10-11), Formula (B-11-1), Formula (B-12-4) shown in the section <<W 1 and W 2 >>, and a single bond, more preferably a group selected from Formula (B-4-1), Formula (B-8-7), Formula (B-12-4), and a single bond, and even more preferably a group selected from Formula (B-4-1) and a single bond.
n41 more preferably represents 0, 1, or 2, even more preferably represents 0 or 1, and still more preferably represents 1.
<M 2 -A1>
In the compound in which <n1 and n2 represent 0 and n3 represents 1>, in a case of significantly considering storage stability when the compound is added to a polymerizable composition, a haze value, evenness of film thickness, unevenness of alignment, and surface hardness, when a film-shaped polymer is prepared, in General Formula (I), M 2 represents Formula (I-M21),
(in the formula, A 31 being present and A 41 being present each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, these groups may be unsubstituted or substituted with one or more of substituents L, and, in a case where a plurality of each of A 31 and A 41 is present, these may be the same as each other or different from each other. Z 31 being present and Z 41 being present each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of each of Z 31 and Z 41 is present, these may be the same as each other or different from each other. m31 and m41 each independently represent an integer of 0 to 5.), and T 21 represents a group selected from Formula (T2-1) to Formula (T2-10).
These groups may be unsubstituted or substituted with one or more of substituents L, and m31+m41 is preferably a group representing 1 to 6.
From viewpoints of availability of raw materials and ease of synthesis, A 31 and A 41 more preferably each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, or a naphthalene-2,6-diyl group which are not substituted or may be substituted with one or more substituent L, more preferably each independently represent a group selected from Formula (A-A1-1) to Formula (A-A1-11),
even more preferably each independently represent a group selected from Formula (A-A1-1) to Formula (A-A1-8), and particularly preferably each independently represent a group selected from Formula (A-A1-1) to Formula (A-A1-4).
From viewpoints of liquid crystal properties of the compound, availability of raw materials, and ease of synthesis, Z 31 and Z 41 preferably each independently represent a single bond, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —CF═CF—, —C≡C—, or a single bond, more preferably each independently represent —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —C≡C—, or a single bond, even more preferably each independently represent —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond, and particularly preferably each independently represent —COO—, —OCO—, or a single bond.
From viewpoints of liquid crystal properties, ease of synthesis, and storage stability, m31 and m41 preferably each independently represent an integer of 1 to 4, more preferably each independently represent an integer of 1 to 3, and particularly preferably each independently represent 1 or 2. m31+m41 preferably each independently represents an integer of 1 to 4 and particularly preferably each independently represent 2, 3, or 4.
T 21 is more preferably a group represented by Formula (T2-1) to Formula (T2-6) and even more preferably a group represented by Formula (T2-1) to Formula (T2-2).
In addition, in a case where M 2 is a group represented by Formula (I-M21), a group selected from <W 1 -A11> to <W 1 -A15> is preferably used and <W 1 -A11>, <W 1 -A12>, or <W 1 -A14> is more preferably used as W 1 .
<M 2 -A2>
In the compound in which <n1 and n2 represent 0 and n3 represents 1>, in a case of significantly considering appearance and alignment defects after ultraviolet light irradiation, when a film-shaped polymer is prepared, in General Formula (I), M 2 represents Formula (I-M22),
(in the formula, A 32 being present and A 42 being present each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, these groups may be unsubstituted or substituted with one or more of substituents L, and, in a case where a plurality of each of A 32 and A 42 is present, these may be the same as each other or different from each other. Z 32 being present and Z 42 being present each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of each of Z 32 and Z 42 is present, these may be the same as each other or different from each other. T 22 represents a trivalent group which may be substituted, and m32 and m42 each independently represent an integer of 0 to 5.), in Formula (I-M22), T 22 represents a group selected from Formula (T2-11) to Formula (T2-27)
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), Formula (T2-28) to Formula (T2-31),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), Formula (T2-32),
(in the formula, a bonding site may be at an arbitrary position, at least one —CH 2 — is each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and Formula (T2-33) or Formula (T2-34),
(in the formulae, a bonding site may be at an arbitrary position, at least one —CH═ is each independently substituted with —N═. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and m32+m42 is preferably a group representing an integer of 1 to 6.
In addition, M 2 represents Formula (I-M222),
(in the formula, A 322 and A 42 each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, these groups may be unsubstituted or substituted with one or more of substituents L, and, in a case where a plurality of each of A 322 and A 422 is present, these may be the same as each other or different from each other. Z 322 and Z 422 each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of each of Z 322 and Z 422 is present, these may be the same as each other or different from each other. T 222 represents a trivalent group which may be substituted), in Formula (I-M222), T 222 represents a group selected from Formula (T2-35) to Formula (T2-41)
(in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), and m322 and m422 preferably each independently represent 1 or 2.
From viewpoints of availability of raw materials and ease of synthesis, A 322 and A 422 preferably represent a 1,4-phenylene group, a 1,4-cyclohexylene group, or a naphthalene-2,6-diyl group which are not substituted or may be substituted with one or more substituent L, more preferably each independently represent a group selected from Formula (A-A2-1) to Formula (A-A2-11),
even more preferably each independently represent a group selected from Formula (A-A2-1) to Formula (A-A2-8), and particularly preferably each independently represent a group selected from Formula (A-A2-1) to Formula (A-A2-4).
From viewpoints of liquid crystal properties of the compound, availability of raw materials, and ease of synthesis, Z 322 and Z 422 preferably each independently represent a single bond, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH—CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH 2 —, —CF═CF—, —C≡C—, or a single bond, more preferably each independently represent —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —C≡C—, or a single bond, even more preferably each independently represent —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond, and particularly preferably each independently represent —COO—, —OCO—, or a single bond.
T 222 is more preferably a group represented by Formula (T2-36), Formula (T2-38), Formula (T2-39), Formula (T2-40), or Formula (T2-41).
<W 1 -A2>
In the compound in which <n1 and n2 represent 0 and n3 represents 1>, in a case of significantly considering appearance and alignment defects after ultraviolet light irradiation, when a film-shaped polymer is prepared, in General Formula (I), W 1 preferably represents a group selected from Formula (I-W19).
(In the formula, V 1 and V 2 each independently represent a single bond or a divalent linking group, B 1 each independently represents a group selected from Formula (B-1) to Formula (B-21),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and a single bond, and n4 represents an integer of 0 to 5.)
V 1 and V 2 are preferably each independently the groups represented by Formula (V-1) to Formula (V-15) shown in the section <(<W 1 and W 2 >> (in the formulae, in a case of including Y 1 , Y 1 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis described in the section <<W 1 and W 2 >>), a single bond, a double bond, —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, and —CH 2 —OCO—, more preferably a group selected from Formula (V-1), Formula (V-2), Formula (V-5), Formula (V-6), Formula (V-7), Formula (V-8), Formula (V-9), Formula (V-12), Formula (V-13), —COO—, and —OCO—, and even more preferably a group selected from Formula (V-5), Formula (V-6), Formula (V-7), Formula (V-8), Formula (V-9), Formula (V-12), Formula (V-13), —COO—, and —OCO—.
B 1 is preferably each independently a group selected from Formula (B-4), Formula (B-8), Formula (B-11), Formula (B-12), and a single bond. More specifically, B 1 is preferably a group selected from Formula (B-4-1), Formula (B-8-7), Formula (B-11-1), Formula (B-12-4) shown in the section <<W 1 and W 2 >>, and a single bond, and more preferably a group selected from Formula (B-4-1), Formula (B-8-7), Formula (B-12-4), and a single bond.
n4 represents preferably 0 to 8 and more preferably represents 0 to 6.
In addition, in a case where T 222 represents a group selected from Formula (T2-35) or Formula (T2-36), in Formula (I-W19), B 1 represents a single bond, n4 represents 1 to 6, and V 1 and V 2 preferably represent a group other than a single bond.
<M 2 -A3>
In the compound in which <n1 and n2 represent 0 and n3 represents 1>, in a case of significantly considering storage stability when the compound is added to a polymerizable composition, evenness of film thickness and alignment defects after ultraviolet light irradiation, when a film-shaped polymer is prepared, in General Formula (I), M represents Formula (I-M23),
(in the formula, A 33 being present and A 43 being present each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, these groups may be unsubstituted or substituted with one or more of substituents L, and, in a case where a plurality of each of A 33 and A 43 is present, these may be the same as each other or different from each other. Z 33 being present and Z 43 being present each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of each of Z 33 and Z 43 is present, these may be the same as each other or different from each other. T 23 represents a trivalent group which may be substituted, and m33 and m43 each independently represent an integer of 0 to 5.), in Formula (I-M23), T 23 represents an acyclic group having 1 to 80 carbon atoms which may be substituted, arbitrary carbon atoms of the acyclic group may be substituted with hetero atoms, and m33+m43 is preferably a group representing an integer of 1 to 6.
In addition, M 2 represents Formula (I-M232),
(in the formula, A 33 being present and A 432 being present each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, these groups may be unsubstituted or substituted with one or more of substituents L, and, in a case where a plurality of each of A 332 and A 432 is present, these may be the same as each other or different from each other. Z 332 being present and Z 43 being present each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of each of Z 332 and Z 432 is present, these may be the same as each other or different from each other. T 232 represents a trivalent group which may be substituted, and m332 and m432 each independently represent an integer of 0 to 5), in Formula (I-M232), T 232 represents a group represented by Formula (T-22),
(in the formula, a bonding site may be at an arbitrary position, arbitrary —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formula, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L, and k1 represents an integer of 1 to 20.), and m332+m432 more preferably represents an integer of 1 to 6.
From viewpoints of availability of raw materials and ease of synthesis, A 332 and A 432 more preferably represent a 1,4-phenylene group, a 1,4-cyclohexylene group, or a naphthalene-2,6-diyl group which are not substituted or may be substituted with one or more substituent L, more preferably each independently represent a group selected from Formula (A-A2-1) to Formula (A-A2-11),
even more preferably each independently represent a group selected from Formula (A-A3-1) to Formula (A-A3-8), and particularly preferably each independently represent a group selected from Formula (A-A3-1) to Formula (A-A3-4).
From viewpoints of liquid crystal properties of the compound, availability of raw materials, and ease of synthesis, Z 332 and Z 432 preferably each independently represent a single bond, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —CF═CF—, —C≡C—, or a single bond, more preferably each independently represent —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —C≡C—, or a single bond, even more preferably each independently represent —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond, and particularly preferably each independently represent —COO—, —OCO—, or a single bond.
From viewpoints of liquid crystal properties, ease of synthesis, and storage stability, m332 and m432 preferably each independently represent an integer of 1 to 4, more preferably each independently represent an integer of 1 to 3, and particularly preferably each independently represent 1 or 2. m31+m41 preferably each independently represent an integer of 1 to 4 and particularly preferably each independently represent 2, 3, or 4.
T 232 preferably represents a group selected from Formula (T-22-1) or Formula (T-22-2),
(in the formulae, arbitrary —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formula, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L, and k131 to k134 represent an integer of 0 to 20), and more preferably represent Formula (T-22-1). It is particularly preferable that k131 and k132 in Formula (T-22-1) represent 1.
<W 1 -A3>
In the compound in which <n1 and n2 represent 0 and n3 represents 1>, in a case of significantly considering storage stability when the compound is added to a polymerizable composition, evenness of film thickness and alignment defects after ultraviolet light irradiation, when a film-shaped polymer is prepared, in General Formula (I), W 1 represents Formula (I-W20).
(In the formula, V 1 and V 2 being present each independently represent a single bond or a divalent linking group, B's being present each independently a group selected from Formula (B-1) to Formula (B-21),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and a single bond, and n4 represents an integer of 0 to 5.)
V 1 and V 2 are preferably each independently the groups represented by Formula (V-1) to Formula (V-15) shown in the section <<W 1 and W 2 >> (in the formulae, in a case of including Y 1 , Y 1 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis described in the section <<W 1 and W 2 >>), a single bond, a double bond, —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, and —CH 2 —OCO—, more preferably a group selected from Formula (V-5), Formula (V-6), Formula (V-8), Formula (V-9), Formula (V-10), and a single bond, and even more preferably a group selected from Formula (V-5), Formula (V-6), Formula (V-8), and Formula (V-9). In addition, from a viewpoint of ease of synthesis, a group directly bonded to T 232 among the groups represented by V 2 is preferably a group other than the group represented by Formula (V-6).
B 1 is preferably each independently a group selected from Formula (B-4), Formula (B-8), Formula (B-11), and a single bond. More specifically, B 1 is preferably a group selected from Formula (B-4-1), Formula (B-8-7), Formula (B-11-1), shown in the section <<W 1 and W 2 >>, and a single bond, and more preferably a group selected from Formula (B-4-1), and a single bond.
<R 3 and R 4 >
In the compound in which <n1 and n2 represent 0 and n3 represents 1>, M 2 and W 1 described above are preferably suitably selected and the following groups are preferably used as R 3 and R 4 .
R 3 represents a group represented by Formula (I-R).
(In the formula, P 1 represents a polymerizable group, S 1 represents a spacer group or a single bond, in a case where a plurality of S 1 is present, these may be the same as each other or different from each other, X 1 represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of X 1 is present in the compound, these may be the same as each other or different from each other (provided that P 1 —(S 1 —X 1 ) k — does not include a —O—O— bond), and k represents an integer of 0 to 10.) R 4 preferably represents a group selected from the group represented by Formula (I-R) and R 5 (in the formula, R 5 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom). Both R 3 and R 4 are particularly preferably the group represented by Formula (I-R), and in this case, the preferable groups and numerical values shown in the section of <<R 1 , R 2 , R 3 , and R 4 >> are respectively applied to P 1 , S 1 , X 1 , and k.
Compound in Which <<n1 Represents 1, n2 Represents 0, and n3 Represents 1>>
<W 1 —B11>
In the compound in which <n1 represents 1, n2 represents 0, and n3 represents 1>, in a case of significantly considering unevenness of alignment and surface hardness, when a film-shaped polymer is prepared, in General Formula (I), W 1 is preferably a group represented by Formula (I-W15).
(In the formula, Y B represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, and in a case where a plurality of Y B is present, these may be the same as each other or different from each other. Alternatively, Y B may represent a group represented by P—(S—X) j —, P represents a polymerizable group, S represents a spacer group or a single bond, in a case where a plurality of S is present, these may be the same as each other or different from each other, X represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of X is present, these may be the same as each other or different from each other (provided that P—(S—X) j — does not include a —O—O— bond), j represents an integer of 0 to 10, B 11 represents a group selected from Formula (B-1) to Formula (B-21)
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L), or a single bond, n41 represents an integer of 0 to 5.) In addition, Y B more preferably represents a hydrogen atom, a fluorine atom, a chlorine atom, a nitro group, a cyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, even more preferably represents a hydrogen atom or a methyl group, and still more preferably represents a hydrogen atom. B 11 is preferably each independently a group selected from Formula (B-4) and Formula (B-11). More specifically, B 11 is specifically preferably a group selected from Formula (B-4-1) and Formula (B-11-1) shown in the section <<W 1 and W 2 >>. n41 more preferably represents 0, 1, or 2, even more preferably represents 0 or 1, and still more preferably represents 0.
<W 1 —B2>
In the compound in which <n1 represents 1, n2 represents 0, and n3 represents 1>, in a case of significantly considering surface hardness and adhesiveness, when a film-shaped polymer is prepared, in General Formula (I), W 1 is preferably a group represented by Formula (I-W21).
(In the formula, V 1 and V 2 each independently represent a single bond or a divalent linking group, B 1 each independently represents a group selected from Formula (B-1) to Formula (B-21),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and a single bond, and n4 represents an integer of 0 to 5.)
V 1 and V 1 are preferably each independently the groups represented by Formula (V-1) to Formula (V-15) shown in the section <<W 1 and W 2 >> (in the formulae, in a case of including Y 1 , Y 1 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis described in the section <<W 1 and W 2 >>), a single bond, a double bond, —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, and —CH 2 —OCO—, more preferably a group selected from Formula (V-1), Formula (V-2), Formula (V-5), Formula (V-6), Formula (V-7), Formula (V-8), Formula (V-9), a single bond, —COO—, —OCO—, —CO—NH—, —NH—CO—, and —CH 2 CH 2 —, even more preferably a group selected from Formula (V-1), Formula (V-2), Formula (V-5), Formula (V-7), a single bond, —COO—, —OCO—, —CO—NH—, —NH—CO—, and —CH 2 CH 2 —, and still more preferably a group selected from Formula (V-1), Formula (V-2), —COO—, —OCO—, —CO—NH—, —NH—CO—, and —CH 2 CH 2 —.
B 1 is preferably each independently a group selected from Formula (B-4), Formula (B-20), and a single bond. More specifically, B 1 is specifically preferably a group selected from Formula (B-4-1), Formula (B-20-2) shown in the section <<W 1 and W2>>, and a single bond.
<W 1 —B3>
In the compound in which <n1 represents 1, n2 represents 0, and n3 represents 1>, in a case of significantly considering adhesiveness, and appearance after ultraviolet light irradiation, when a film-shaped polymer is prepared, in General Formula (I), W1 is preferably a group represented by Formula (I-W22).
(In the formula, V 2 and V 2 each independently represent a single bond or a divalent linking group, B 1 each independently represents a group selected from Formula (B-1) to Formula (B-21),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and a single bond, and n4 represents an integer of 0 to 5.)
V 1 and V 2 are preferably each independently the groups represented by Formula (V-1) to Formula (V-15) shown in the section <<W 1 and W 2 >> (in the formulae, in a case of including Y 1 , Y 1 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis described in the section <<W 1 and W 2 >>), a single bond, a double bond, —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, and —CH 2 —OCO—, more preferably a group selected from Formula (V-6), Formula (V-7), Formula (V-8), Formula (V-9), Formula (V-10), a single bond, —COO—, —OCO—, —CS—NH—, and —NH—CS—, and even more preferably a group selected from Formula (V-8), Formula (V-9), —COO—, and —OCO—.
B 1 is preferably each independently a group selected from Formula (B-4), Formula (B-11), and a single bond, and more preferably each independently a group selected from Formula (B-4) and a single bond. More specifically, B 1 is preferably a group selected from Formula (B-4-1), Formula (B-11-1) shown in the section <<W 1 and W 2 >>, and a single bond, and more preferably a group selected from Formula (B-4-1) and a single bond.
<M 1 -B and M 2 -B>
In the compound in which <n1 represents 1, n2 represents 0, and n3 represents 1>, unevenness of alignment, surface hardness, or adhesiveness, when a film-shaped polymer is prepared, are excellent due to the structure of the compound. Therefore, in General Formula (I), M 1 represents a group represented by Formula (I-M14) and M 2 represents a group represented by Formula (I-M24).
(In the formula, A 14 , A 24 , A 34 , and A 44 each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, these groups may be unsubstituted or substituted with one or more of substituents L, and, in a case where a plurality of each of A 14 , A 24 , A 34 , and A 44 is present, these may be the same as each other or different from each other. Z 14 , Z 24 , Z 34 , and Z 44 each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of each of Z 14 , Z 24 , Z 34 , and Z 44 is present, these may be the same as each other or different from each other. m14, m24, m34, and m44 each independently represent an integer of 0 to 5.)
In Formula (I-M14) and Formula (I-M24), T 14 and T 24 are preferably each independently a group selected from Formula (T-1) to Formula (T-22).
(In the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L, and k1 represents an integer of 1 to 20.) In addition, T 14 and T 24 preferably each independently represent one group selected from Formula (T-1) to Formula (T-22) and even more preferably each independently represent the same group.
From viewpoints of availability of raw materials and ease of synthesis, A 14 , A 24 , A 34 , and A 44 preferably represent a 1,4-phenylene group, a 1,4-cyclohexylene group, or a naphthalene-2,6-diyl group which are not substituted or may be substituted with one or more substituent L, more preferably each independently represent a group selected from Formula (A-A2-1) to Formula (A-A2-11),
even more preferably each independently represent a group selected from Formula (A-A3-1) to Formula (A-A3-8), and particularly preferably each independently represent a group selected from Formula (A-A3-1) to Formula (A-A3-4).
From viewpoints of liquid crystal properties of the compound, availability of raw materials, and ease of synthesis, Z 14 , Z 24 , Z 34 , and Z 44 preferably each independently represent a single bond, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —CF═CF—, —C≡C—, or a single bond, more preferably each independently represent —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —C≡C—, or a single bond, even more preferably each independently represent —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond, and particularly preferably each independently represent —COO—, —OCO—, or a single bond.
From viewpoints of liquid crystal properties of the compound, ease of synthesis, and storage stability, m14, m24, m34, and m44 preferably each independently represent an integer of 1 to 4, more preferably each independently represent an integer of 1 to 3, and particularly preferably each independently represent 1 or 2. m14+m24 and m34+m44 preferably each independently represent an integer of 1 to 4 and more preferably each independently represent 2, 3, or 4.
<M 1 -B11 and M 2 -B11>
In a case of significantly considering unevenness of alignment and surface hardness, when a film-shaped polymer is prepared, T 14 in Formula (I-M14) preferably represents the component described above and T 24 in Formula (I-M24) preferably represents a group selected from Formula (T2-1) to Formula (T2-10).
These groups may be unsubstituted or substituted with one or more of substituents L.
In addition, T 24 is more preferably a group represented by Formula (T2-1) to Formula (T2-6) and even more preferably a group represented by Formula (T2-1) or Formula (T2-2). Further, T 14 represents a group selected from Formula (T1-1) to Formula (T1-10).
These groups may be unsubstituted or substituted with one or more of substituents L. It is more preferable that T 24 represents a group selected from Formula (T2-1) to Formula (T2-10) and these groups may be unsubstituted or substituted with one or more of substituents L. It is even more preferable that T 14 represents a group selected from Formula (T1-1) to Formula (T1-6) and T 24 represents a group selected from Formula (T2-1) to Formula (T2-6). It is still more preferable that T 14 represents a group selected from Formula (T1-1) or Formula (T1-2) and T 24 represents a group selected from Formula (T2-1) or Formula (T2-2).
<M 1 -B2>
In addition, in a case of significantly considering surface hardness and adhesiveness, when a film-shaped polymer is prepared, T 14 in Formula (I-M14) represents the component shown in the section <M 1 -B and M 2 -B>, and T 24 in Formula (I-M24) represents a group selected from Formula (T2-11) to Formula (T2-27),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L.), Formula (T2-28) to Formula (T2-31),
(in the formulae, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L.), Formula (T2-32),
(in the formula, a bonding site may be at an arbitrary position, at least one —CH 2 — is each independently substituted with —O—, —S—, —NR 0 — (in the formula, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L.), and Formula (T2-33) or Formula (T2-34),
(in the formulae, a bonding site may be at an arbitrary position, and at least one —CH═ is each independently substituted with —N═. In addition, these groups may be unsubstituted or substituted with one or more of L.), and m34+m44 is preferably a group representing an integer of 1 to 6.
Further, T 24 in Formula (I-M24) particularly preferably represents a group selected from Formula (T2-35) to Formula (T2-41).
(In the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.) Further, it is more preferable that T 14 in Formula (I-M14) represents a group selected from Formula (T1-11) to Formula (T1-27),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L.), Formula (T1-28) to Formula (T1-31),
(in the formulae, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L.), Formula (T1-32),
(in the formula, a bonding site may be at an arbitrary position, at least one —CH 2 — is each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L.), and Formula (T1-33) or Formula (T1-34),
(in the formulae, a bonding site may be at an arbitrary position, at least one —CH═ is each independently substituted with —N═. In addition, these groups may be unsubstituted or substituted with one or more of L.), and T 24 in Formula (I-M24) represents a group selected from Formula (T2-11) to Formula (T2-41). Further, it is even more preferable that T 14 in Formula (I-M14) represents a group selected from Formula (T1-35) to Formula (T1-41),
(in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), and T 24 in Formula (I-M24) represents a group selected from Formula (T2-35) to Formula (T2-41). In addition, in a case where T 14 represents a group selected from Formula (T1-40) or Formula (T1-41) and T 24 represents a group selected from Formula (T2-40) or Formula (T2-41), in Formula (I-W21), V 1 and V 2 preferably represent a group other than the group represented by Formula (V-6).
<M 1 -B3>
In addition, in a case of significantly considering adhesiveness, and appearance after ultraviolet light irradiation, when a film-shaped polymer is prepared, it is preferable that T 14 in Formula (I-M14) represents the component described above and T 24 represents an acyclic group having 1 to 80 carbon atoms which may be substituted, and one or more of arbitrary carbon atoms of the acyclic group may be substituted with hetero atoms.
Further, T 24 preferably represents a group represented by Formula (T-22)
(in the formula, a bonding site may be at an arbitrary position, arbitrary —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formula, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L, and k1 represents an integer of 1 to 20.), preferably represents a group selected from Formula (T-22-1) or Formula (T-22-2),
(in the formulae, arbitrary —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formula, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L, and k131 to k134 represent an integer of 0 to 20), and more preferably represents Formula (T-22-1). It is even more preferable that k131 and k132 in Formula (T-22-1) represent 1. In addition, in Formula (T-22-1), k131 represents 0 and k132 represents 1. In a case where k131 represents 1 and k132 represents 0, in Formula (I-W22), a group represented by V 2 directly bonded to T 14 and T 24 preferably represents a group other than Formula (V-6) and a single bond. Further, it is preferable that both T 14 and T 24 represent a group represented by Formula (T-22), it is more preferable that both T 14 and T 24 represent a group represented by Formula (T-22-1) or Formula (T-22-2), and it is even more preferable that both T 14 and T 24 represent Formula (T-22-1).
<R 1 , R 2 , R 3 , and R 4 >
Meanwhile, in the compound in which <n1 represents 1, n2 represents 0, and n3 represents 1>, unevenness of alignment, surface hardness, or adhesiveness, when a film-shaped polymer is prepared, are excellent due to the structure of the compound. Therefore, in General Formula (I), M 1 , M 2 , and W 1 described above are preferably suitably selected and the following groups are preferably used as R 1 to R 4 .
R 4 and R 3 represent a group represented by Formula (I-R).
(In the formula, P represents a polymerizable group, S represents a spacer group or a single bond, in a case where a plurality of S is present, these may be the same as each other or different from each other, X represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of X is present in the compound, these may be the same as each other or different from each other (provided that P—(S—X) k — does not include a —O—O— bond), k represents an integer of 0 to 10.) R 1 and R 4 preferably represent a group selected from the group represented by Formula (I-R) and R 5 (in the formula, R 5 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom).
In addition, in the compound in which <n1 represents 1, n2 represents 0, and n3 represents 1>, in a case of significantly considering unevenness of alignment and surface hardness, when a film-shaped polymer is prepared, in General Formula (I), it is preferable that R 2 and R 3 represent a group represented by Formula (I-R) and R 1 and R 4 represent a group represented by R 5 , and in this case, the preferable groups and numerical values shown in the section of <<R 1 , R 2 , R 3 , and R 4 >> are respectively applied to P, S, X, k, and R 5 .
Further, in the compound in which <n1 represents 1, n2 represents 0, and n3 represents 1>, in a case of significantly considering surface hardness and adhesiveness, when a film-shaped polymer is prepared, or in a case of significantly considering adhesiveness, and appearance after ultraviolet light irradiation, when a film-shaped polymer is prepared, all of R 1 , R 2 , R 3 , and R 4 are particularly preferably a group represented by Formula (I-R), and in this case, the preferable groups and numerical values shown in the section of <<R 1 , R 2 , R 3 , and R 4 >> are respectively applied to P, S, X, and k.
Compound in which <<n1 Represents 0, and n2 and n3 Represent 1>>
<M 2 -C>
In addition, in the compound in which <n1 represents 0, and n2 and n3 represent 1>, evenness of film thickness, surface hardness, and/or alignment defects after ultraviolet light irradiation, when a film-shaped polymer is prepared, are excellent due to the structure of the compound. Therefore, in General Formula (I), M 2 represents Formula (I-M2C).
(In the formula, A 3C being present and A 4C being present each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, these groups may be unsubstituted or substituted with one or more of substituents L, and, in a case where a plurality of each of A 3C and A 4C are present, these may be the same as each other or different from each other. Z 3C and Z 4C each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of each of Z 3C and Z 4C is present, these may be the same as each other or different from each other. m3C and m4C each independently represent an integer of 0 to 5.) In Formula (I-M 2 C), T 2C preferably represents a group selected from Formula (T-1) to Formula (T-22)
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L, and k1 represents an integer of 1 to 20.), and these groups preferably represent groups which may be unsubstituted or substituted with one or more of substituents L.
From viewpoints of availability of raw materials and ease of synthesis, A 3C and A 4C preferably represent a 1,4-phenylene group, a 1,4-cyclohexylene group, or a naphthalene-2,6-diyl group which are not substituted or may be substituted with one or more substituent L, more preferably each independently represent a group selected from Formula (A-C-1) to Formula (A-C-11),
even more preferably each independently represent a group selected from Formula (A-C-1) to Formula (A-C-8), and particularly preferably each independently represent a group selected from Formula (A-C-1) to Formula (A-C-4).
From viewpoints of liquid crystal properties of the compound, availability of raw materials, and ease of synthesis, Z 3 c and Z 4C preferably each independently represent a single bond, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH—CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —CF═CF—, —C≡C—, or a single bond, more preferably each independently represent —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —C≡C—, or a single bond, even more preferably each independently represent —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond, and particularly preferably each independently represent —COO—, —OCO—, or a single bond.
From viewpoints of liquid crystal properties, ease of synthesis, and storage stability, m3C and m4C preferably each independently represent an integer of 1 to 4, more preferably each independently represent an integer of 1 to 3, and particularly preferably each independently represent 1 or 2. m3C+m4C preferably each independently represent an integer of 1 to 4 and more preferably each independently represent 2, 3, or 4.
<M 2 -C11 and M 2 -C12>
In a case of significantly considering evenness of film thickness, when a film-shaped polymer is prepared, T 2C in Formula (I-M2C) represents a group selected from Formula (T2-C-1) to Formula (T2-C-12).
These groups are preferably groups which may be unsubstituted or substituted with one or more of substituents L.
In addition, T 2C is more preferably a group represented by Formula (T2-C-1) to Formula (T2-C-4) and even more preferably a group represented by Formula (T2-C-1) or Formula (T2-C-4).
<M 2 -C2>
In addition, in a case of significantly considering storage stability of a composition, and alignment defects after ultraviolet light irradiation, when a film-shaped polymer is prepared, T 2C in Formula (I-M2C) preferably represents a group selected from Formula (T2-C-13) to Formula (T2-C-42).
(In the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L.) T 2C more preferably represents a group selected from Formula (T2-C-13), Formula (T2-C-22), Formula (T2-C-27), Formula (T2-C-28), Formula (T2-C-29), Formula (T2-C-36), Formula (T2-C-37), Formula (T2-C-38), Formula (T2-C-39), and Formula (T2-C-41), even more preferably represents a group selected from Formula (T2-C-13), Formula (T2-C-27), and Formula (T2-C-29), and still more preferably represents Formula (T2-C-13).
<M 2 -C3>
In addition, in a case of significantly considering surface hardness and alignment defects after ultraviolet light irradiation, when a film-shaped polymer is prepared, it is preferable that T 2C in Formula (I-M2C) represents an acyclic group having 1 to 80 carbon atoms which may be substituted, and one or more of arbitrary carbon atoms of the acyclic group may be substituted with hetero atoms.
Further, T 2C preferably represents a group represented by Formula (T-22)
(in the formula, a bonding site may be at an arbitrary position, arbitrary —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formula, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L, and k1 represents an integer of 1 to 20.), and more preferably represents a group selected from Formula (T-22-3),
(in the formula, arbitrary —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formula, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L, and k141 and k142 represent an integer of 0 to 20). k141 and k42 in Formula (T-22-3) more preferably represent an integer of 1 to 10, k141 and k42 in Formula (T-22-3) even more preferably represent an integer of 1 to 4, and k141 and k42 in Formula (T-22-3) particularly preferably represent 1.
<W 1 -M 2 -W 2 —C1>
In the compound in which <n1 represents 0, and n2 and n3 represent 1>, due to the structure of the compound, evenness of film thickness, when a film-shaped polymer is prepared, is high, surface hardness is high, and/or alignment defects after ultraviolet light irradiation hardly occurs. Therefore, in General Formula (I), the groups shown in the section <M 2 -C11 and M 2 -C12> are preferably used as M 2 , and a group represented by W 1 -M 2 -W 2 (provided that M 2 is linked to R 3 and R 4 at arbitrary positions) preferably represents a group selected from Formula (I-W16-1) or Formula (I-W16-2).
(In the formula, Y C1 and Y C4 each independently represent a group including aromatic and/or nonaromatic carbon ring or heterocyclic ring having 1 to 80 carbon atoms which may be substituted, and one or more of arbitrary carbon atoms of the carbon ring or the heterocyclic ring may be substituted with hetero atoms (provided that oxygen atoms are not directly bonded to each other). Y C2 and Y C3 each independently represent a hydrogen atom or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, Y C2 and Y C3 may represent a group having 5 to 30 carbon atoms including at least one aromatic group, the group may be unsubstituted or substituted with one or more of substituents L. Y C represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, and in a case where a plurality of Y C is present, these may be the same as each other or different from each other. Alternatively, Y C may represent a group represented by P—(S—X) j —, P represents a polymerizable group, S represents a spacer group or a single bond, in a case where a plurality of S is present, these may be the same as each other or different from each other, X represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of X is present, these may be the same as each other or different from each other (provided that P—(S—X) j — does not include a —O—O— bond), j represents an integer of 0 to 10, Y C1 and Y C2 may be integrated to form a ring structure, and Y C3 and Y C4 may be integrated to form a ring structure.)
From viewpoints of liquid crystal properties and ease of synthesis, Y C in Formula (I-W16-1) and Formula (I-W16-2) preferably represents a linear or branched alkyl group having 1 to 12 carbon atoms, in which one or more of arbitrary hydrogen atoms in the group may be substituted with a fluorine atom and one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, or —OCO—, more preferably represents a linear or branched alkyl group having 1 to 12 carbon atoms, in which one or more of arbitrary hydrogen atoms in the group may be substituted with a fluorine atom, and particularly preferably represents a linear alkyl group having 1 to 12 carbon atoms.
Y C1 and Y C4 in Formula (I-W16-1) and Formula (I-W16-2) preferably each independently a group represented by Formula (B-1) to Formula (B-21).
(In the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.) Y C1 and Y C4 more preferably each independently a group selected from Formula (B-8) and Formula (B-12). More specifically, Y C1 and Y C4 are preferably a group selected from Formula (B-8-1) and Formula (B-12-1) shown in the section <<W 1 and W 2 >>.
From viewpoints of availability of raw materials and ease of synthesis, in a case where Y C2 and Y C3 in Formula (I-W16-1) and Formula (I-W16-2) each independently represent a hydrogen atom, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and one or more of arbitrary hydrogen atoms may be substituted with a fluorine atom, Y C2 and Y C3 preferably each independently represent a hydrogen atom, or a linear or branched alkyl group having 1 to 12 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —CO—, —COO—, or —OCO—, and one or more of arbitrary hydrogen atoms may be substituted with a fluorine atom, more preferably each independently represent a hydrogen atom, or a linear or branched alkyl group having 1 to 12 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —CO—, —COO—, or —OCO—, even more preferably each independently represent a hydrogen atom, or a linear alkyl group having 1 to 8 carbon atoms, and still more preferably each independently represent a hydrogen atom. In addition, from viewpoints of availability of raw materials and ease of synthesis, in a case where Y C2 and Y C3 represent a group having 5 to 30 carbon atoms including at least one aromatic group, which may be unsubstituted or substituted with one or more of substituents L, Y C2 and Y C3 are preferably each independently a group represented by Formula (B-1) to Formula (B-21),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), Y C2 and Y C3 are more preferably each independently a group selected from Formula (B-8) and Formula (B-12). More specifically, the group selected from Formula (B-8-1) and Formula (B-12-1) shown in the section <<W 1 and W 2 >>is preferable.
In addition, in a case where Y C1 and Y C2 or Y C3 and Y C4 in Formula (I-W16-1) and Formula (I-W16-2) are integrated to form a ring structure, Y C1 and Y C2 or Y C3 and Y C4 preferably represent a group selected from Formula (Y—C-1) to Formula (Y—C-29),
(in the formulae, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and more preferably a group represented by Formula (Y—C-26).
<W 1 -M 2 -W 2 —C2>
In the compound in which <n1 represents 0, and n2 and n3 represent 1>, in a case of significantly considering storage stability of a composition, alignment defects, when a film-shaped polymer is prepared and irradiated with ultraviolet light, a group represented by W 1 and W 2 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis, among General Formula (I-W1) and General Formula (I-W2) shown in the section <<W 1 and W 2 >>.
In General Formula (I-W1) and General Formula (I-W2), V 1 , V 2 , V 3 , and V 4 preferably each independently represent a group represented by Formula (V-1) to Formula (V-15) described in the section <<W 1 and W 2 >> (in the formulae, in a case of including Y 1 , Y 1 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis described in the section <<W 1 and W 2 >>), a single bond, a double bond, —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, and —CH 2 —OCO—, more preferably each independently represent Formula (V-1), Formula (V-2), Formula (V-3), Formula (V-4), Formula (V-5), Formula (V-6), Formula (V-7), Formula (V-11), a single bond, or a double bond, even more preferably each independently represent Formula (V-1), Formula (V-2), Formula (V-3), Formula (V-4), Formula (V-5), or a single bond, and still more preferably each independently represent a single bond.
In General Formula (I-W1) and General Formula (I-W2), B 1 , B 2 , and B 3 preferably each independently represent a group selected from Formula (B-1) to Formula (B-21)
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and a single bond. B 1 , B 2 , and B 3 are preferably a group selected from Formula (B-4), Formula (B-8), Formula (B-11), Formula (B-12), and a single bond, and more preferably a group selected from Formula (B-4), Formula (B-8), and a single bond. More specifically, B 1 , B 2 , and B 3 are preferably a group selected from Formula (B-4-1), Formula (B-8-6), Formula (B-8-7), Formula (B-11-1), Formula (B-11-2), Formula (B-12-1), Formula (B-12-2) shown in the section <<W 1 and W 2 >>, and a single bond, more preferably a group selected from Formula (B-4-1), Formula (B-8-6), Formula (B-8-7), and a single bond, and even more preferably a group selected from Formula (B-4-1) and a single bond.
<W 1 -M 2 -W 1 —C3>
In the compound in which <n1 represents 0, and n2 and n3 represent 1>, in a case of significantly considering surface hardness, when a film-shaped polymer is prepared, and alignment defects, when the film is irradiated with ultraviolet light, a group represented by W 1 and W 2 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis described in the section <<W 1 and W 2 >>.
V 1 , V 2 , V 3 , and V 4 preferably each independently represent a group represented by Formula (V-1) to Formula (V-15) described in the section <<W 1 and W 2 >> (in the formulae, in a case of including Y 1 , Y 1 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis described in the section <<W 1 and W 2 >>), a single bond, a double bond, —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, and —CH 2 —OCO—, more preferably each independently represent Formula (V-1), Formula (V-2), Formula (V-6), Formula (V-8), Formula (V-9), Formula (V-10), a single bond, —CH 2 —, —COO—, —OCO—, —CS—NH—, —NH—CS—, or —CH 2 CH 2 —, even more preferably each independently represent Formula (V-6), Formula (V-8), Formula (V-9), —CH 2 —, —COO—, or —OCO—, and still more preferably each independently represent Formula (V-8) or Formula (V-9).
B 1 , B 2 , and B 3 preferably each independently represent a group selected from Formula (B-1) to Formula (B-21)
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and a single bond. B 1 , B 2 , and B 3 are preferably a group selected from Formula (B-3), Formula (B-4), Formula (B-7), Formula (B-11), Formula (B-12), and a single bond, and more preferably a group selected from Formula (B-4), Formula (B-12), and a single bond. More specifically, B 1 , B 2 , and B 3 are preferably a group selected from Formula (B-3-2), Formula (B-4-1), Formula (B-7-9), Formula (B-7-11), Formula (B-11-1), Formula (B-12-4) shown in the section <<W 1 and W 2 >>, and a single bond, more preferably a group selected from Formula (B-4-1), Formula (B-12-4), and a single bond, and even more preferably a group selected from Formula (B-4-1) and a single bond.
<R 3 and R 4 >
In the compound in which <n1 represents 0, and n2 and n3 represent 1>, M 2 , W 1 , and W 1 described above are preferably suitably selected and the following groups are preferably respectively used for R 3 and R 4 .
R 3 represents a group represented by Formula (I-R).
(In the formula, P represents a polymerizable group, S represents a spacer group or a single bond, in a case where a plurality of S is present, these may be the same as each other or different from each other, X represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of X is present in the compound, these may be the same as each other or different from each other (provided that P—(S—X) k — does not include a —O—O— bond), k represents an integer of 0 to 10.) R 4 preferably represent a group selected from the group represented by Formula (I-R) and R 5 (in the formula, R 5 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom). Both R 3 and R 4 are particularly preferably a group represented by Formula (I-R), and in this case, the preferable groups and numerical values shown in the section of <<R 1 , R 2 , R 3 , and R 4 >> are respectively applied to P, S, X, and k.
Compound in Which <<n1 and n2 Represent 0 and n3 Represents 2 to 1,000>>
<W 1 -D1>
In the compound in which <n1 and n2 represent 0 and n3 represents 2>, evenness of film thickness or adhesiveness, when a film-shaped polymer is prepared, is excellent due to the structure of the compound. Therefore, in General Formula (I), W 1 preferably represents a group selected from by Formula (I-W17-1) or Formula (I-W17-2).
(In the formulae, Y D1 represents a group including aromatic and/or nonaromatic carbon ring or heterocyclic ring having 1 to 80 carbon atoms which may be substituted, arbitrary carbon atoms of the carbon ring or the heterocyclic ring may be substituted with hetero atoms (provided that oxygen atoms are not directly bonded to each other). Y D2 represents a hydrogen atom or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, Y D2 may represent a group having 2 to 30 carbon atoms including at least one aromatic group, the group may be unsubstituted or substituted with one or more of substituents L. Y D represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, and in a case where a plurality of Y D is present, these may be the same as each other or different from each other. Alternatively, Y D2 may represent a group represented by P—(S—X) j —, P represents a polymerizable group, S represents a spacer group or a single bond, in a case where a plurality of S is present, these may be the same as each other or different from each other, X represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of X is present, these may be the same as each other or different from each other (provided that P—(S—X) j — does not include a —O—O— bond), j represents an integer of 0 to 10, Y D1 and Y D2 may be integrated to form a ring structure.)
In addition, from viewpoints of liquid crystal properties and ease of synthesis, Y D preferably represents a linear or branched alkyl group having 1 to 12 carbon atoms, in which one or more of arbitrary hydrogen atoms in the group may be substituted with a fluorine atom and one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, or —OCO—, more preferably represents a linear or branched alkyl group having 1 to 12 carbon atoms, in which one or more of arbitrary hydrogen atoms in the group may be substituted with a fluorine atom, and particularly preferably represents a linear alkyl group having 1 to 12 carbon atoms.
Further, Y D1 is preferably a group represented by Formula (B-1) to Formula (B-21).
(In the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.) Y D1 is more preferably a group selected from Formula (B-3), Formula (B-8), Formula (B-11), and Formula (B-12). More specifically, Y D1 is preferably a group selected from Formula (B-3-5), Formula (B-8-7), Formula (B-11-1), and Formula (B-12-1) shown in the section <<W 1 and W 2 >>, more preferably a group selected from Formula (B-8-7) and Formula (B-12-1), and even more preferably a group represented by Formula (B-8-7).
From viewpoints of availability of raw materials and ease of synthesis, in a case where Y D2 each independently represent a hydrogen atom, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and one or more of arbitrary hydrogen atoms may be substituted with a fluorine atom, Y D2 preferably each independently represent a hydrogen atom, or a linear or branched alkyl group having 1 to 12 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —CO—, —COO—, or —OCO—, and one or more of arbitrary hydrogen atoms may be substituted with a fluorine atom, more preferably each independently represent a hydrogen atom, or a linear or branched alkyl group having 1 to 12 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —CO—, —COO—, or —OCO—, even more preferably each independently represent a hydrogen atom, or a linear alkyl group having 1 to 8 carbon atoms, and still more preferably each independently represent a hydrogen atom. In addition, from viewpoints of availability of raw materials and ease of synthesis, in a case where Y D2 represents a group having 5 to 30 carbon atoms including at least one aromatic group, which may be unsubstituted or substituted with one or more of substituents L, Y D2 is preferably a group represented by Formula (B-1) to Formula (B-21),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and Y D2 is more preferably a group selected from Formula (B-3), Formula (B-8), Formula (B-11), and Formula (B-12). More specifically, Y D2 is preferably a group selected from Formula (B-3-5), Formula (B-8-7), Formula (B-11-1), and Formula (B-12-1) shown in the section <<W 1 and W 2 >>, more preferably a group selected from Formula (B-8-7) and Formula (B-12-1), and even more preferably a group represented by Formula (B-8-7).
In addition, in a case where Y D1 and Y D2 are integrated to form a ring structure, Y D1 and Y D2 preferably represent a group selected from Formula (Y-D-1) to Formula (Y-D-29),
(in the formulae, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and more preferably a group represented by Formula (Y-D-26).
<W 1 -D2>
In the compound in which <n1 and n2 represent 0 and n3 represents 2>, in a case of significantly considering haze and adhesiveness, when a film-shaped polymer is prepared, a group represented by W 1 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis, among General Formula (I-W1) shown in the section <<W 1 and W 2 >>.
In General Formula (I-W1), V 1 and V 2 preferably each independently represents the groups represented by Formula (V-1) to Formula (V-15) shown in the section <<W 1 and W 2 >> (in the formulae, in a case of including Y 1 , Y 1 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis described in the section <<W 1 and W 2 >>), a single bond, a double bond, —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, or —CH 2 —OCO—, more preferably represent Formula (V-1), Formula (V-2), Formula (V-3), Formula (V-4), Formula (V-5), Formula (V-6), Formula (V-7), Formula (V-8), Formula (V-9), a single bond, —COO—, or —OCO—, even more preferably represent Formula (V-5), Formula (V-8), Formula (V-9), or a single bond, and still more preferably represent a single bond.
In General Formula (I-W1), B 1 preferably each independently represents a group selected from Formula (B-1) to Formula (B-21).
(In the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L), and a single bond.
B 1 is preferably a group selected from Formula (B-4), Formula (B-8), Formula (B-11), Formula (B-12), and a single bond, and more preferably a group selected from Formula (B-8), Formula (B-12), and a single bond. More specifically, B 1 is preferably a group selected from Formula (B-4-1), Formula (B-8-2), Formula (B-8-7), Formula (B-11-1), Formula (B-12-1), Formula (B-12-4) shown in the section <<W 1 and W 2 >>, and a single bond, more preferably a group selected from Formula (B-8-2), Formula (B-12-4) and a single bond, and even more preferably a group represented by Formula (B-8-2).
<W 1 -D3>
In the compound in which <n1 and n2 represent 0 and n3 represents 2>, in a case of significantly considering haze and surface hardness, when a film-shaped polymer is prepared, a group represented by W 1 and W 2 is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis, among General Formula (I-W1) shown in the section <<W 1 and W 2 >>.
In General Formula (I-W1), V 1 and V 2 preferably each independently represent the groups represented by Formula (V-1) to Formula (V-15) shown in the section <<W 1 and W 2 >> (in the formulae, in a case of including Y 1 , Y is preferably a group selected from viewpoints of availability of raw materials and ease of synthesis described in the section <<W 1 and W 2 >>), a single bond, a double bond, —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —CH 2 —, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CS—NH—, —NH—CS—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, and —CH 2 —OCO—, more preferably represent Formula (V-5), Formula (V-6), Formula (V-7), Formula (V-8), Formula (V-9), Formula (V-10), a single bond, —COO—, —OCO—, —CS—NH—, and —NH—CS—, and even more preferably represent Formula (V-6), Formula (V-8), Formula (V-9), —COO—, and —OCO—.
In General Formula (I-W1), B 1 preferably each independently represents a group selected from Formula (B-1) to Formula (B-21),
(In the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L.), and a single bond. B 1 is preferably a group selected from Formula (B-4), Formula (B-8), Formula (B-11), and a single bond, and more preferably a group selected from Formula (B-4) and a single bond. More specifically, B 1 is preferably a group selected from Formula (B-4-1), Formula (B-8-6), Formula (B-8-7), Formula (B-11-1) shown in the section <<W 1 and W 2 >>, and a single bond, and more preferably a group selected from Formula (B-4-1) and a single bond.
<-(M 2 ) 2 ->
In the compound in which <n1 and n2 represent 0 and n3 represents 2>, a haze value, evenness of film thickness, or adhesiveness, when a film-shaped polymer is prepared, are excellent due to the structure of the compound. Therefore, in General Formula (I), -(M 2 ) 2 - is preferably a group represented by General Formula (I-M3).
(In the formula, A 5 , A 6 , A 7 , and A8 being present each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, these groups may be unsubstituted or substituted with one or more of substituents L, and, in a case where a plurality of A 5 , A 6 , A 7 , and A 8 is present, these may be the same as each other or different from each other. Z 5 , Z 6 , Z 7 , and Z 8 being present each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of each of Z 5 , Z 6 , Z 7 , and Z 8 is present, these may be the same as each other or different from each other. X 1 and X 2 represent —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of X 2 is present in the compound, these may be the same as each other or different from each other, S 1 represents a single bond or a linear or branched alkylene group having 1 to 20 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, —OCO—, —OCO—O—, —CO—NH—, —NH—CO—, —CH═CH—, or —C≡C—, in a case where a plurality of S 1 is present, these may be the same as each other or different from each other (provided that X 1 —S 1 and S 1 —X 2 do not include a —O—O— bond.), kD represents an integer of 0 to 8, m5, m6, m7, and m8 each independently represent an integer of 0 to 5, total of m5, m6, m7, and m8 represents 0 to 6, T 3 and T 4 each independently represent a group selected from Formula (T-1) to Formula (T-22)
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of substituents L, and kD represents an integer of 1 to 20).) In addition, both T 3 and T 4 preferably represent one group selected from Formula (T-1) to Formula (T-22) and T 3 and T 4 more preferably represent the same group.
In addition, from viewpoints of availability of raw materials and ease of synthesis, A 5 , A 6 , A 7 , and A 8 preferably represent a 1,4-phenylene group, a 1,4-cyclohexylene group, or a naphthalene-2,6-diyl group which are not substituted or may be substituted with one or more substituent L, more preferably each independently represent a group selected from Formula (A-D-1) to Formula (A-D-11),
even more preferably each independently represent a group selected from Formula (A-D-1) to Formula (A-D-8), and particularly preferably each independently represent a group selected from Formula (A-D-1) to Formula (A-D-4).
In addition, from viewpoints of liquid crystal properties of the compound, availability of raw materials, and ease of synthesis, Z 5 , Z 6 , Z 7 , and Z 8 preferably each independently represent a single bond, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —CF═CF—, —C≡C—, or a single bond, more preferably each independently represent —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —C≡C—, or a single bond, even more preferably each independently represent —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond, and particularly preferably each independently represent —COO—, —OCO—, or a single bond.
In addition, from viewpoints of liquid crystal properties of the compound, ease of synthesis, and storage stability, m5, m6, m7, and m8 preferably each independently represent an integer of 1 to 4, more preferably each independently represent an integer of 1 to 3, and particularly preferably each independently represent 1 or 2. The total of m5, m6, m7, and m8 preferably each independently represents an integer of 2 to 4.
In addition, S-preferably each independently represents a linear alkylene group having 1 to 20 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, —OCO—, —OCO—O—, —CO—NH—, —NH—CO—, —CH═CH—, or —C≡C—, more preferably each independently represents a linear alkylene group having 1 to 12 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, or —OCO—, and even more preferably each independently represents a linear alkylene group having 1 to 6 carbon atoms.
In addition, X 1 and X 2 preferably represent —O—, —CO—, —COO—, —OCO—, —CO—NH—, —NH—CO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, or a single bond and more preferably represent —O—, —COO—, —OCO—, or a single bond.
In addition, kD preferably represents an integer of 0 to 4, more preferably represents an integer of 0 to 2, even more preferably represents 1 or 2, and still more preferably represents 1.
<-(M 2 ) 2 -D1>
In the compound in which <n1 and n2 represent 0 and n3 represents 2>, in a case of significantly considering storage stability of the composition, adhesiveness, when a film-shaped polymer is prepared, and appearance after ultraviolet light irradiation, or in a case of significantly considering evenness of film thickness and unevenness of alignment, when a film-shaped polymer is prepared, in General Formula (I-M3), T 3 and T 4 each independently represent a group selected from Formula (T2-1) to Formula (T2-10).
These groups preferably represent a group which may be unsubstituted or substituted with one or more of substituents L, and more preferably represent a group represented by Formula (T2-1) and Formula (T2-2). In addition, both T 3 and T 4 preferably represent one group selected from Formula (T2-1) to Formula (T2-10) and T 3 and T 4 more preferably represent the same group.
<-(M 2 ) 2 -D2>
In the compound in which <n1 and n2 represent 0 and n3 represents 2>, in a case of significantly considering haze and adhesiveness, when a film-shaped polymer is prepared, in General Formula (I-M3), T 3 's each independently represent a group selected from Formula (T2-11) to Formula (T2-27),
(in the formulae, a bonding site may be at an arbitrary position, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L.), Formula (T2-28) to Formula (T2-31),
(in the formulae, arbitrary —CH═ may be each independently substituted with —N═, —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L.), Formula (T2-32),
(in the formula, a bonding site may be at an arbitrary position, at least one —CH 2 — is each independently substituted with —O—, —S—, —NR 0 — (in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L.), and Formula (T2-33) or Formula (T2-34),
(in the formulae, a bonding site may be at an arbitrary position, at least one —CH═ is each independently substituted with —N═. In addition, these groups may be unsubstituted or substituted with one or more of L.). In General Formula (I-M3), T 4 preferably represents a group selected from Formula (T2-1) to Formula (T2-10) or Formula (T2-11) to Formula (T2-34).
In addition, T 3 more preferably represents a group selected from Formula (T2-35) to Formula (T2-41),
(in the formulae, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), even more preferably represents a group selected from Formula (T2-36), Formula (T2-40), and Formula (T2-41), and still more preferably represents Formula (T2-36). In addition, both T 3 and T 4 preferably represent a group selected from Formula (T2-35) to Formula (T2-41), more preferably represent a group selected from Formula (T2-36), Formula (T2-40), and Formula (T2-41), and still more preferably represent Formula (T2-36).
<-(M 2 ) 2 -D3>
In the compound in which <n1 and n2 represent 0 and n3 represents 2>, in a case of significantly considering haze and surface hardness, when a film-shaped polymer is prepared, T 3 preferably represents an acyclic group having 1 to 80 carbon atoms which may be substituted, and arbitrary carbon atoms of the acyclic group may be substituted with hetero atoms.
In addition, in General Formula (I-M3), T 3 preferably represents Formula (T-22)
(in the formula, a bonding site may be at an arbitrary position, arbitrary —CH 2 — may be each independently substituted with —O—, —S—, —NR— (in the formula, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L, and k1 represents an integer of 1 to 20.), preferably represents a group selected from Formula (T-22-1) or Formula (T-22-2),
(in the formulae, arbitrary —CH 2 — may be each independently substituted with —O—, —S—, —NR 0 — (in the formula, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO—, provided that a —O—O— bond is not included. In addition, these groups may be unsubstituted or substituted with one or more of L, and k131 to k134 represent an integer of 0 to 20), and more preferably represents Formula (T-22-1). It is even more preferable that k131 and k132 in Formula (T-22-1) represent 1. In addition, both T 3 and T 4 preferably represent a group represented by Formula (T-22), more preferably represent a group selected from Formula (T-22-1) or Formula (T-22-2), and even more preferably represent Formula (T-22-1).
<R 3 and R 4 >
In the compound in which <n1 and n2 represent 0 and n3 represents 2>, M 2 and W 1 described above are preferably suitably selected and the following groups are preferably respectively used as R 3 and R 4 . R 3 represents a group represented by Formula (I-R).
(In the formula, P represents a polymerizable group, S represents a spacer group or a single bond, in a case where a plurality of S is present, these may be the same as each other or different from each other, X represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of X is present in the compound, these may be the same as each other or different from each other (provided that P—(S—X) k — does not include a —O—O— bond), k represents an integer of 0 to 10.) R 4 preferably represents a group selected from the group represented by Formula (I-R) and R 5 (in the formula, R 5 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom). Both R 3 and R 4 are particularly preferably a group represented by Formula (I-R), and in this case, the preferable groups and numerical values shown in the section of <<R 1 , R 2 , R 3 , and R 4 >> are respectively applied to P, S, X, and k.
In the compound in which n3 represents 3 to 1,000 in the compound in which <n1 and n2 represent 0 and n3 represents 2 to 1,000>, haze, appearance after ultraviolet light irradiation, and alignment defects, when a film-shaped polymer is prepared, are excellent due to the structure of the compound. Therefore, in General Formula (I), the preferable groups and numerical values shown in the sections of <W 1 -D1>, <W 1 -D2>, and <W 1 -D3> are applied to W 1 . In addition, in General Formula (I), the preferable groups and numerical values shown in the sections of <-(M 2 ) 2 -D1>, <-(M 2 ) 2 -D2>, and <-(M 2 ) 2 -D3> are applied to -(M 2 ) n3 -.
In a case of significantly considering reverse dispersibility, the compound represented by General Formula (I) is preferably a compound represented by General Formula (I-z1) and/or General Formula (I-z2).
More specifically, in a case of significantly considering reverse dispersibility, solubility in a solvent, ease of synthesis, availability of raw materials, liquid crystal properties, hardening shrinkage in a case where a film is obtained, and reduced warp, a compound represented by General Formula (I) is preferably a compound represented by General Formula (I-z1).
In the formula, P z1 represents a polymerizable group and preferably represents a group selected from Formula (P-1) to Formula (P-20), and the polymerizable groups are polymerized by radical polymerization, radical addition polymerization, cation polymerization, and anion polymerization. Particularly, in a case of performing ultraviolet ray polymerization as a polymerization method, Formula (P-1), Formula (P-2), Formula (P-3), Formula (P-4), Formula (P-5), Formula (P-7), Formula (P-11), Formula (P-13), Formula (P-15), or Formula (P-18) is preferable, Formula (P-1), Formula (P-2), Formula (P-7), Formula (P-11), or Formula (P-13) is more preferable, Formula (P-1), Formula (P-2), or Formula (P-3) is even more preferable, and Formula (P-1) or Formula (P-2) is particularly preferable. S z1 represents a spacer group or a single bond, and in a case where a plurality of S z1 is present, these may be the same as each other or different from each other. From viewpoints of liquid crystal properties, availability of raw materials, and ease of synthesis, in a case where a plurality of S z1 is present, these may be the same as each other or different from each other, and S z1 's preferably each independently represent an alkylene group having 1 to 20 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, or —C≡C—, and a single bond. In a case where a plurality of S z1 is present, these may be the same as each other or different from each other, and S z1 's more preferably each independently represent a linear alkylene group having 1 to 20 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, —OCO—, or —OCO—O—, or a single bond. In a case where a plurality of S z1 is present, these may be the same as each other or different from each other, and S z1 's even more preferably each independently represent a linear alkylene group having 1 to 12 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, still more preferably each independently represent a linear alkylene group having 1 to 12 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, and particularly preferably represent a linear alkylene group having 1 to 12 carbon atoms. X z1 represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, and in a case where a plurality of X is present, these may be the same as each other or different from each other (provided that P z1 —(S z1 —X z1 ) kz — does not include a —O—O— bond). From viewpoints of availability of raw materials and ease of synthesis, in a case where a plurality of X z1 is present, these may be the same as each other or different from each other, X z1 's preferably each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond, more preferably each independently represent —O—, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond. In a case where a plurality of X z1 is present, these may be the same as each other or different from each other, and X z1 's particularly preferably each independently represent —O—, —COO—, —OCO—, or a single bond. A z1 and A z2 each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, these groups may be unsubstituted or substituted with one or more of L described above, and, in a case where a plurality of each of A z1 and A z2 is present, these may be the same as each other or different from each other. The preferable structure of A z1 and A z2 is the same as that in a case of A 1 , A 2 , A 3 , and A 4 . Z z1 and Z z2 each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, in a case where a plurality of each of Z z1 and Z z2 is present, these may be the same as each other or different from each other. From viewpoints of liquid crystal properties of the compound, availability of raw materials, and ease of synthesis, Z z1 and Z z2 preferably each independently represent a single bond, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —CF═CF—, —C≡C—, or a single bond, more preferably each independently represent —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —CH═CH—, —C≡C—, or a single bond, even more preferably each independently represent —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond, still more preferably each independently represent —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond, and particularly preferably each independently represent —OCH 2 —, —CH 2 O—, —COO—, —OCO—, or a single bond.
M z represents a group selected from Formula (M-z-1) to Formula (M-z-8).
These groups may be unsubstituted or substituted with one or more of L Mz . L Mz represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, and in a case where a plurality of L Mz is present, these may be the same as each other or different from each other. From viewpoints of availability of raw materials and ease of synthesis, M z preferably each independently represents a group selected from Formula (M-z-1) or Formula (M-z-2) which may be unsubstituted or substituted with one or more of L Mz , or Formula (M-z-3) to Formula (M-z-6) which may not be substituted, more preferably represents a group selected from Formula (M-z-1) or Formula (M-z-2) which may be unsubstituted or substituted with one or more of L Mz , and particularly preferably represents a group selected from Formula (M-z-1) or Formula (M-z-2) which may not be substituted. R z1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a cyano group, a nitro group, an isocyano group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—, —CF═CF—, or —C≡C—, and one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom. From viewpoints of liquid crystal properties and ease of synthesis, R z1 preferably represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, or a linear or branched alkyl group having 1 to 12 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —COO—, —OCO—, or —O—CO—O—, more preferably a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, or a linear alkyl group or a linear alkoxy group having 1 to 12 carbon atoms, even more preferably a hydrogen atom, or a linear alkyl group or a linear alkoxy group having 1 to 12 carbon atoms, and particularly preferably a linear alkyl group or a linear alkoxy group having 1 to 12 carbon atoms. G z is preferably a compound represented by Formula (G-z-1) or Formula (G-z-2),
(in the formulae, R z2 represents a hydrogen atom, or a linear or branched alkyl group having 1 to 20 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, W z1 represents a group having 2 to 30 carbon atoms including at least one aromatic group, the group may be unsubstituted or substituted with one or more of L Wz . L Wz represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, and in a case where a plurality of L Wz is present, these may be the same as each other or different from each other. W Z2 represents a hydrogen atom, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom. Alternatively, W z2 may represent a group having 2 to 30 carbon atoms including at least one aromatic group, the group may be unsubstituted or substituted with one or more of substituents L Wz . W z1 and W z2 may be integrated to form a ring structure. kz represents an integer of 0 to 8. From viewpoints of liquid crystal properties, availability of raw materials, ease of synthesis, kz preferably represents an integer of 0 to 4, more preferably represents an integer of 0 to 2, even more preferably represents 0 or 1, and particularly preferably represents 1. mz1 and mz2 each independently represent an integer of 0 to 5 and mz1+mz2 represents an integer of 1 to 5. From viewpoints of liquid crystal properties, ease of synthesis, and storage stability, mz1 and mz2 preferably each independently represent an integer of 1 to 4, more preferably each independently represent an integer of 1 to 3, and particularly preferably represent 1 or 2. mz1+mz2 preferably represents an integer of 1 to 4 and particularly preferably represents 2 or 3), and more preferably represents a compound selected from General Formula (I-z1-A) to General Formula (I-z1-D).
(In the formulae, P z1 , S z1 , X z1 , kz, M z , G z , and R z1 represent the same meaning as those in General Formula (I-z1), A z11 and A z12 each independently represent the same meaning as A z1 in General Formula (I-z1), Z z11 and Z z12 each independently represent the same meaning as Z z1 in General Formula (I-z1), A z21 and A z22 each independently represent the same meaning as A z2 in General Formula (I-z1), and Z z21 and Z z22 each independently represent the same meaning as Z z2 in General Formula (I-z1).) From viewpoints of balance between refractive index anisotropy and reverse dispersibility, A z11 in General Formula (I-z1-A) and General Formula (I-z1-B) more preferably represents 1,4-phenylene group which may be unsubstituted or substituted with the substituent L, A z11 in General Formula (I-z1-C) and General Formula (I-z1-D) represents a 1,4-phenylene group which may be unsubstituted or substituted with the substituent L, A z12 more preferably represents a 1,4-cyclohexylene group which may be unsubstituted or substituted with the substituent L. In addition, A z21 in General Formula (I-z1-A) to General Formula (I-z1-D) represents a 1,4-phenylene group or a 1,4-cyclohexylene group which may be unsubstituted or substituted with the substituent L, and A z22 more preferably represents a 1,4-cyclohexylene group which may be unsubstituted or substituted with the substituent L. In General Formula (I-z1-A) to General Formula (I-z1-D), from viewpoints of liquid crystal properties, ease of synthesis, and storage stability, a compound represented by General Formula (I-z1-A) to General Formula (I-z1-C) is more preferable and a compound represented by General Formula (I-z1-A) or General Formula (I-z1-C) is particularly preferable. In a case where it is necessary to obtain a higher transition temperature T NI from a nematic phase to an isotropic phase, a compound represented by General Formula (I-z1-C) is particularly preferable.
From viewpoints of reverse dispersibility, solubility in a solvent, ease of synthesis, availability of raw materials, and liquid crystal properties, even more specifically, a compound represented by General Formula (I-z1) even more preferably represents a compound selected from General Formula (I-z1-A-1) to General Formula (I-z1-D-2).
(In the formulae, P z1 , S z1 , X z1 , kz, L, R z2 , W z1 , W z2 , and R z1 represent the same meaning as those in General Formula (I-z1), s represents an integer of 0 to 4, t represents an integer of 0 to 3, A z211 represents the same meaning as A z2 in General Formula (I-z1), and Z z111 and Z z121 each independently represent the same meaning as Z z1 in General Formula (I-z1). The preferable structure of each group is the same as that in General Formula (I-z1).) In General Formula (I-z1-A-1) to General Formula (I-z1-D-2), from viewpoints of liquid crystal properties, ease of synthesis, and storage stability, a compound represented by General Formula (I-z1-A-1) to General Formula (I-z1-C-2) is more preferable and a compound represented by General Formula (I-z1-A-1), General Formula (I-z1-A-2), General Formula (I-z1-C-1), or General Formula (I-z1-C-2) is particularly preferable. In a case where it is necessary to obtain reverse wavelength dispersibility of a short wavelength side, a compound represented by General Formula (I-z1-A-1) or General Formula (I-z1-C-1) is particularly preferable. In a case where it is necessary to obtain balance between reverse wavelength dispersibility and refractive index anisotropy, a compound represented by General Formula (I-z1-A-2) or General Formula (I-z1-C-2) is particularly preferable. In a case where it is necessary to obtain a higher transition temperature T NI from a nematic phase to an isotropic phase, a compound represented by General Formula (I-z1-C-1) or General Formula (I-z1-C-2) is particularly preferable. In a case where it is necessary to obtain reverse wavelength dispersibility of a long wavelength side, a compound represented by General Formula (I-z1-C-1) is particularly preferable.
In addition, W z1 particularly preferably represents a group selected from Formula (W-a-1) to Formula (W-a-6).
(In the formulae, r represents an integer of 0 to 5, s represents an integer of 0 to 4, and t represents an integer of 0 to 3.)
In addition, R z2 is more preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which is not substituted or substituted with one or more of F, and particularly preferably a hydrogen atom.
Further, in a case of significantly considering reverse dispersibility and liquid crystal properties, W z2 is preferably a hydrogen atom.
In a case of significantly considering a degree how hardly a change in quality occurs, in a case the compound is dissolved in an organic solvent and stored for a long period of time, a degree how hardly a change in quality occurs, in a case the compound is added to the composition and stored for a long period of time, or stability of a phase difference in a case where a film is obtained, W z2 preferably represents a linear or branched alkyl group having 1 to 20 carbon atoms, in which one or more of arbitrary hydrogen atoms in the group may be substituted with a fluorine atom and one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —CO—, —COO—, or —OCO—, or a group represented by —(X z4 —S z4 ) kz —P z4 (in the formula, P z4 represents the same meaning as P z1 , and S z4 represents the same meaning as S z1 , and X z4 represents the same meaning as X z1 ). Among the groups described above, W 2 more preferably represents a linear alkyl group having 1 to 12 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, or a group represented by —(X z4 —S z4 ) kz —P z4 . More specifically, from a viewpoint of ease of synthesis, W z2 more preferably represents a linear or branched alkyl group having 1 to 20 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, or a group represented by —(X z4 —S z4 ) kz —P z4 , and even more preferably represents a linear alkyl group having 1 to 12 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, or a group represented by —(X z4 —S z4 ) kz —P z4 .
In a case of significantly considering balance between reverse dispersibility, high refractive index anisotropy, and high liquid crystal properties, in a case where the compound is added to the composition, a degree how hardly a change in quality occurs, in a case the compound is dissolved in an organic solvent and stored for a long period of time, a degree how hardly a change in quality occurs, in a case the compound is added to the composition and stored for a long period of time, or stability of a phase difference in a case where a film is obtained, W z2 is preferably a compound represented by General Formula (I-z2).
(In the formula, kz, M z , and G z represent the same meaning as those in General Formula (I-z1), P z2 and P z3 each independently represent the same meaning as P z1 in General Formula (I-z1), S z2 and S z3 each independently represent the same meaning as S z1 in General Formula (I-z1), X z2 and X z3 each independently represent the same meaning as X z1 in General Formula (I-z1), A z3 and A z4 each independently represent the same meaning as A z1 and A z2 in General Formula (I-z1), Z z3 and Z z4 each independently represent the same meaning as Z z1 and Z z2 in General Formula (I-z1), mz3 and mz4 each independently represent an integer of 0 to 5, and mz3+mz4 represents an integer of 1 to 5). In a case of significantly considering balance between reverse dispersibility, high refractive index anisotropy, and high liquid crystal properties, when the compound is added to the composition, W z2 is preferably General Formula (I-z2-A) and General Formula (I-z2-B).
(In the formulae, P z2 , P z3 , S z2 , S z3 , M z , and G z represent the same meaning as those in General Formula (I-z2), A z31 , A z42 , A z33 , and A z43 each independently represent a 1,4-phenylene group, the group may be unsubstituted or substituted with one or more of substituents L z11 . L z11 represents a fluorine atom, a chlorine atom, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —CO—, —COO—, or —OCO—, and one or more of arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom. In a case where a plurality of L z11 are present in the compound, these may be the same as each other or different from each other. A z32 and A z41 represent a 1,4-cyclohexylene group, Z z31 and Z z42 each independently represent —OCH 2 —, —CH 2 O—, —COO—, —OCO—, or a single bond, Z z32 , Z z41 , Z z33 , and Z z43 each independently represent —OCH 2 —, —CH 2 O—, —COO—CH 2 CH 2 —, —CH 2 CH 2 —OCO—, —COO—, or —OCO—, and at least one of Z z32 and Z z41 and at least one of Z z33 and Z z43 represent a group selected from —OCH 2 —, —CH 2 O—, —COO—CH 2 CH 2 —, or —CH 2 CH 2 —OCO—.)
In a case of significantly considering balance between reverse dispersibility, high refractive index anisotropy, and high liquid crystal properties, in a case where the compound is added to the composition, a degree how hardly a change in quality occurs, in a case the compound is dissolved in an organic solvent and stored for a long period of time, a degree how hardly a change in quality occurs, in a case the compound is added to the composition and stored for a long period of time, or stability of a phase difference in a case where a film is obtained, W z2 is preferably a compound represented by General Formula (I-z2-A-1).
(In the formula, P z2 , P z3 , S z2 , S z3 , X z2 , X z3 , M z , R z2 , W z1 represent the same meaning as those in General Formula (I-z1), A z311 and A z421 each independently represent a 1,4-phenylene group, the group may be unsubstituted or substituted with one or more of substituents L z11 . A z321 and A z411 represent a 1,4-cyclohexylene group, Z z311 and Z z421 each independently represent —OCH 2 —, —CH 2 O—, —COO—, or —OCO—, Z z321 and Z z411 each independently represent —OCH 2 —, —CH 2 O—, —COO—CH 2 CH 2 —, —CH 2 CH 2 —OCO—, —COO—, or —OCO—, and at least one of Z z321 and Z z411 particularly preferably represents a group selected from —OCH 2 —, —CH 2 O—, —COO—CH 2 CH 2 —, or —CH 2 CH 2 —OCO—. W z21 represents a group selected from a linear or branched alkyl group having 1 to 20 carbon atoms in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, or a group represented by —(X z4 —S z4 ) kz —P z4 .) The preferable structure of W z1 is the same as that described above.
Specifically, the compounds represented by General Formula (I) are preferably compounds represented by the following formulae.
The total content of the reverse dispersible compound represented by General Formula (I) is preferably 10% to 95% by mass, more preferably 30% to 95% by mass, and particularly preferably 60% to 95% by mass, with respect to the total amount of the polymerizable compound used in the polymerizable composition (that is, the total content of the reverse dispersible compound represented by General Formula (I) and the total content of the compound represented by General Formula (II)).
<<General Formula (II)>>
In the present invention, a compound represented by General Formula (II) is included as an essential component.
In the formula, P 21 represents a polymerizable functional group, S 21 represents an alkylene group having 1 to 18 carbon atoms (hydrogen atoms in the alkylene group may be substituted with one or more halogen atoms, a CN group, or an alkyl group having 1 to 8 carbon atoms including a polymerizable functional group, and one CH 2 group or two or more of (—CH 2 —)'s that are not adjacent to each other present in this group may be each independently substituted with —O—, —COO—, —OCO—, or —OCO—O—), X 21 represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF—S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond (provided that P 21 —S 21 and S 21 —X 21 do not include a —O—O—, —O—NH—, —S—S—, and —O—S— group), q1 represents 0 or 1, MG represents a mesogenic group, R 21 represents a hydrogen atom, a halogen atom, a cyano group, or a linear or a branched alkyl group having 1 to 12 carbon atoms, the alkyl group may be linear or branched, and one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other of the alkyl group may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—. Alternatively, R 21 represents General Formula (II-a).
[Chem. 200]
—(X 22 —S 22 ) q2 —P 23 (II-a)
(In the formula, P 23 represents a polymerizable functional group, S 22 represents a component which is the same as that defined in the description regarding S 21 , X 22 represents a component which is the same as that defined in the description regarding X 21 (provided that P 23 —S 22 and S 22 —X 22 do not include a —O—O—, —O—NH—, —S—S—, and —O—S— group), q 2 represents 0 or 1). A mesogenic group represented by MG described above is represented by General Formula (II-b).
[Chem. 201]
-(B1-Z1) r1 —B2-Z2-B3- (II-b)
(In the formula, B1, B2, and B3 each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a 1,4-cyclohexenyl group, a tetrahydropyran-2,5-diyl group, a 1,3-dioxane-2,5-diyl group, a tetrahydrothiopyran-2,5-diyl group, a 1,4-bicyclo (2,2,2) octylene group, a decahydronaphthalene-2,6-diyl group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a pyrazine-2,5-diyl group, a thiophene-2,5-diyl group-, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a 2,6-naphthylene group, a phenanthrene-2,7-diyl group, a 9,10-dihydrophenanthrene-2,7-diyl group, a 1,2,3,4,4a,9,10a-octahydrophenanthrene-2,7-diyl group, a 1,4-naphthylene group, a benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl group, a benzo[1,2-b:4,5-b′]diselenophene-2,6-diyl group, a [1]benzothieno[3,2-b]thiophene-2,7-diyl group, a [1]benzoselenopheno[3,2-b] selenophene-2, 7-diyl group, or a fluorene-2,7-diyl group. As a substituent, one or more of F, Cl, CF 3 , OCF 3 , a CN group, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkanoyl group having 1 to 8 carbon atoms, an alkanoyloxy group having 1 to 8 carbon atoms, an alkoxycarbonyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkenyloxy group having 2 to 8 carbon atoms, an alkenoyl group having 2 to 8 carbon atoms, an alkenoyloxy group having 2 to 8 carbon atoms, and/or General Formula (II-c)
[Chem. 202]
—(X 23 ) q4 —(S 23 ) q3 —P 24 (II-c)
(in the formula, P 4 represents a reactive functional group, S 23 represents a component which is the same as that defined in the description regarding S 21 , X 23 represents —O—, —COO—, —OCO—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 OCO—, —COOCH 2 CH 2 —, —OCOCH 2 CH 2 —, or a single bond, q 3 represents 0 or 1, and q 4 represents 0 or 1 (provided that P 24 —S 23 and S 23 —X 23 do not include a —O—O—, —O—NH—, —S—S— or —O—S— group).) may be included. B1, B2, and B3 are preferably a 1,4-cyclohexylene group, a 1,4-cyclohexenyl group, a tetrahydropyran-2,5-diyl group, a 1,3-dioxane-2,5-diyl group, a tetrahydrothiopyran-2,5-diyl group, a 1,4-bicyclo (2,2,2) octylene group, or a decahydronaphthalene-2,6-diyl group (as a substituent, one or more of F, Cl, CF 3 , OCF 3 , a CN group, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkanoyl group having 1 to 8 carbon atoms, an alkanoyloxy group having 1 to 8 carbon atoms, an alkoxycarbonyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkenyloxy group having 2 to 8 carbon atoms, an alkenoyl group having 2 to 8 carbon atoms, an alkenoyloxy group having 2 to 8 carbon atoms, and/or General Formula (II-c)), Z1 and Z2 each independently represent —COO—, —OCO—, —CH 2 CH 2 —, —OCH 2 —, —CH 2 O—, —CH═CH—, —C≡C—, —CH═CHCOO—, —OCOCH═CH—, —CH 2 CH 2 COO—, —CH 2 CH 2 OCO—, —COOCH 2 CH 2 —, —OCOCH 2 CH 2 —, —C═N—, —N═C—, —CONH—, —NHCO—, —C(CF 3 ) 2 —, an alkyl group having 2 to 10 carbon atoms which may include a halogen atom, or a single bond, r1 represents 0, 1, 2, or 3, and in a case where a plurality of each of B1 and Z1 is present, these may be respectively the same as each other or different from each other, and r1 is preferably 0.)
In the present invention, as a preferable halogen atom, a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom is preferable, a fluorine atom or a chlorine atom is more preferable, and a fluorine atom is particularly preferable. The same applies to a halogen atom described below.
P 22 , P 23 , and P 24 preferably each independently represent a substituent selected from a polymerizable group represented by Formula (P-2-1) to Formula (P-2-20).
From a viewpoint of increasing polymerizability, among these polymerizable functional groups, Formula (P-2-1), Formula (P-2-2), Formula (P-2-7), Formula (P-2-12), and Formula (P-2-13) are preferable, and Formula (P-2-1) and Formula (P-2-2) are more preferable.
(Monofunctional Polymerizable Liquid Crystal Compound)
Among the compounds represented by General Formula (II), a compound represented by General Formula (II-2-1) is preferable, as a monofunctional polymerizable liquid crystal compound including one polymerizable functional group in a molecule.
[Chem. 204]
P 21 —(S 21 —X 21 ) q1 -MG-R 21 (II-2-1)
In the formulae, P 21 , S 21 , X 21 , q1, and MG respectively represent the same definition as those in General Formula (II), R 21 represents a hydrogen atom, a halogen atom, a cyano group, or a linear or branched alkyl group having 1 to 12 carbon atoms or a linear or branched alkenyl group having 1 to 12 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —NH—, —N(CH 3 )—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, one hydrogen atom or two or more hydrogen atoms in the alkyl group and the alkenyl group may be substituted with halogen atoms or cyano groups, and in a case where a plurality of atoms are substituted, these may be the same as each other or different from each other. The monofunctional polymerizable liquid crystal compound has characteristics in which polarities of both ends are different from each other, compared to a multifunctional polymerizable liquid crystal compound. In a case where the polymerizable composition of the present invention is applied onto a base material, a hydrophobic group tends to easily appear on a side of an air interface. Accordingly, by adding the monofunctional polymerizable liquid crystal compound and suitably selecting the kind of a surfactant which will be described later and an amount thereof added, it is possible to control an angle of alignment of polymerizable liquid crystals in the air interface, that is, a tilt angle.
As examples of General Formula (II-2-1), compounds represented by General Formulae (II-2-1-1) to (II-2-1-4) can be used, but there is no limitation to the general formulae below.
[Chem. 205]
P 21 —(S 21 —X 21 ) q1 —B2-Z2-B3-R 21 (II-2-1-1)
P 21 —(S 21 —X 21 ) q1 -B11-Z11-B2-Z2-B3-R 21 (II-2-1-2)
P 21 —(S 21 —X 21 ) q1 -B11-Z11-B12-Z12-B2-Z2-B3-R 21 (II-2-1-3)
P 21 —(S 21 —X 21 ) q1 -B11-Z12-Z12-B13-Z13-B2-Z2-B3-R 21 (II-2-1-4)
In the formulae, P 21 , S 21 , X 21 , and q1 respectively represent the same definition as those in General Formula (II) (in a case of controlling tilt, S 21 is preferably an alkylene group having 3 to 18 carbon atoms (one or more of arbitrary hydrogen atoms in the alkylene group may be substituted with a halogen atom, a cyano group, or an alkyl group having 1 to 8 carbon atoms including a polymerizable functional group, and one CH 2 group or two or more of (—CH 2 —)'s that are not adjacent to each other present in this group may be each independently substituted with —O—, —COO—, —OCO—, or —OCO—O—).
B11, B12, B13, B2, and B3 represent the same definition as B1 to B3 of General Formula (II-b), and these may be respectively the same as each other or different from each other.
Z1, Z12, Z13, and Z2 represent the same definition as Z1 to Z3 of General Formula (II-b), and these may be respectively the same as each other or different from each other. R 21 represents a hydrogen atom, a halogen atom, a cyano group, or a linear or branched alkyl group having 1 to 12 carbon atoms or a linear or branched alkenyl group having 1 to 12 carbon atoms, in which one —CH 2 — or two or more of (—CH 2 —)'s that are not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —NH—, —N(CH 3 )—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, one hydrogen atom or two or more hydrogen atoms in the alkyl group and the alkenyl group may be substituted with halogen atoms or cyano groups, and in a case where a plurality of atoms are substituted, these may be the same as each other or different from each other. Meanwhile, in a case R 21 is a cyano group, S 21 is preferably an alkylene group having 3 to 18 carbon atoms (hydrogen atoms in the alkylene group may be substituted with one or more halogen atoms, a cyano group, or an alkyl group having 1 to 8 carbon atoms including a polymerizable functional group, one CH 2 group or two or more of (—CH 2 —)'s that are not adjacent to each other present in this group may be each independently substituted with —O—, —COO—, —OCO—, or —OCO—O—), from a viewpoint in that the tilt is easily controlled, in a case of having different polarities on both ends of the compound.
As the compounds represented by General Formulae (II-2-1-1) to (II-2-1-4), compounds represented by General Formula (II-2-1-1-1) to General Formula (II-2-1-1-32) are used, but there is no limitation thereto.
In the formulae, R c represents a hydrogen atom or a methyl group, m represents an integer of 0 to 18, n represents 0 or 1, R 21 represents the same definition as those in General Formulae (II-2-1-1) to (II-2-1-4), R 21 preferably represents a hydrogen atom, a halogen atom, a cyano group, or a linear alkyl group having 1 to 6 carbon atoms or a linear alkenyl group having 1 to 6 carbon atoms, in which one —CH 2 — may be substituted with —O—, —CO—, —COO—, or —OCO—, R 21 more preferably represents a halogen atom or a cyano group, and in a case where R 21 represents a cyano group, m is preferably an integer of 3 to 18, from a viewpoint in that the tilt is easily controlled, in a case of having different polarities on both ends of the compound, as described above.
The cyclic group described above may include one or more of F, Cl, CF 3 , OCF 3 , a CN group, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkanoyl group having 1 to 8 carbon atoms, an alkanoyloxy group having 1 to 8 carbon atoms, an alkoxycarbonyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkenyloxy group having 2 to 8 carbon atoms, an alkenoyl group having 2 to 8 carbon atoms, or an alkenoyloxy group having 2 to 8 carbon atoms, as a substituent.
More specifically, compounds represented by the following formulae are preferable.
The total content of the monofunctional polymerizable liquid crystal compound including one polymerizable functional group in one molecule is preferably 0% to 90% by mass, more preferably 0% to 85% by mass, and particularly preferably 0% to 80% by mass, with respect to total amount of the compound represented by General Formula (II) used. In a case of significantly considering alignment of an optically anisotropic body, the lower limit value is preferably equal to or greater than 5% by mass and more preferably equal to or greater than 10% by mass, and in a case of significantly considering hardness of a coated film, the upper limit value is preferably equal to or smaller than 80% by mass and more preferably equal to or smaller than 70% by mass.
(Bifunctional Polymerizable Liquid Crystal Compound)
Among the compounds represented by General Formula (II), a compound represented by General Formula (II-2-2) is preferable, as a bifunctional polymerizable liquid crystal compound including two polymerizable functional groups in a molecule.
[Chem. 213]
P 21 —(S 21 —X 21 ) q1 -MG-(X 22 —S 22 ) q2 P 23 (II-2-2)
In the formula, P 21 , S 21 , X 21 , q1, MG, X 22 , S 22 , q2, and P 23 respectively represent the same definition as those in General Formula (II). As examples of General Formula (II-2-2), compounds represented by General Formulae (II-2-2-1) to (II-2-2-4) can be used, but there is no limitation to General Formulae below.
[Chem. 214]
P 21 —(S 21 —X 21 ) q1 -B2-Z2-B3-(X 22 —S 22 ) q2 P 23 (II-2-2-1)
P 21 —(S 21 —X 21 ) q1 B11-Z11-B2-Z2-B3-(X 22 —S 22 ) q2 —P 23 (II-2-2-2)
P 21 —(S 21 —X 21 ) q1 -B11-Z11-BIZ B2-Z2-B23-(X 22 —S 22 ) q2 —P 23 (II-2-2-3)
P 21 —(S 21 —X 21 ) q1 —B11-Z11-B12-Z12-B13-Z13-B2-Z2-B3-(X 22 —S 22 ) q2 P 23 (II-2-2-4)
In the formulae, P 21 , S 21 , X 21 , q1, MG, X 22 , S 22 , q2, and P 23 respectively represent the same definition as those in General Formula (II), B11, B12, B13, B2, and B3 represent the same definition as B1 to B3 of General Formula (II-b), and these may be respectively the same as each other or different from each other. Z11, Z 12 , Z 13 , and Z2 represent the same definition as Z1 to Z3 of General Formula (II-b), and these may be respectively the same as each other or different from each other.
Among the compounds represented by General Formulae (II-2-2-1) to (II-2-2-4), it is preferable to use the compounds represented by General Formulae (II-2-2-2) to (II-2-2-4) having three or more of ring structures in the compound, because alignment of an optically anisotropic body to be obtained is excellent and hardenability is excellent. It is particularly preferable to use a compound represented by General Formula (II-2-2-2) having three or more of ring structures in the compound.
As the compounds represented by General Formulae (II-2-2-1) to (II-2-2-4), compounds represented by General Formula (1I-2-2-1-1) to General Formula (II-2-2-1-45) are used, but there is no limitation thereto.
In the formulae, R d and R e each independently represent a hydrogen atom or a methyl group, and the cyclic group may include one or more of F, Cl, CF 3 , OCF 3 , a CN group, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkanoyl group having 1 to 8 carbon atoms, an alkanoyloxy group having 1 to 8 carbon atoms, an alkoxycarbonyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkenyloxy group having 2 to 8 carbon atoms, an alkenoyl group having 2 to 8 carbon atoms, or an alkenoyloxy group having 2 to 8 carbon atoms, as a substituent.
m1 and m2 each independently represent an integer of 0 to 18, and n1, n2, n3, and n4 each independently represent 0 or 1.
More specifically, compounds represented by the following formulae are preferable.
The total content of the bifunctional polymerizable liquid crystal compound including two polymerizable functional groups in a molecule is preferably 10% to 100% by mass, more preferably 15% to 85% by mass, and particularly preferably 20% to 80% by mass, with respect to the total amount of the compound represented by General Formula (II) used. In a case of significantly considering hardness of a coated film, the lower limit value is preferably equal to or greater than 30% by mass and more preferably equal to or greater than 50% by mass, and in a case of significantly considering alignment of an optically anisotropic body, the upper limit value is preferably equal to or smaller than 85% by mass and more preferably equal to or smaller than 80% by mass.
(Multifunctional Polymerizable Liquid Crystal Compound)
As a multifunctional polymerizable liquid crystal compound including three or more of polymerizable functional groups, a compound including three polymerizable functional groups is preferably used. Among the compounds represented by General Formula (II), a compound represented by General Formula (1I-2-3) is preferable, as a multifunctional polymerizable liquid crystal compound including three polymerizable functional groups in a molecule.
In the formula, P 21 , S 21 , X 21 , q1, MG, X 22 , S 22 , q2, P 23 , X 23 , q4, S 23 , q3, P 24 respectively represent the same definition as those in General Formula (II). As examples of General Formula (II-2-3), compounds represented by General Formulae (II-2-3-1) to (II-2-3-8) can be used, but there is no limitation to General Formulae below.
In the formulae, P 21 , S 21 , X 21 , q1, MG, X 22 , S 22 , q2, P 23 , X 23 , q4, S 23 , q3, P 24 respectively represent the same definition as those in General Formula (II), B 31 , B 32 , B 22 , B 23 represent the same definition as B 21 to B 23 of General Formula (II-b), and these may be respectively the same as each other or different from each other. Z 52 , Z 53 , and Z 54 represent the same definition as Z 51 and Z 52 of General Formula (II-b), and these may be respectively the same as each other or different from each other.
As the compounds represented by General Formulae (II-2-3-1) to (II-2-3-5), compounds represented by General Formula (II-2-3-1-1) to General Formula (II-2-3-1-6) are used, but there is no limitation thereto.
In the formulae, R f , R g , and R h each independently represent a hydrogen atom or a methyl group, R i , R j , and R k each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a cyano group. In a case where these groups are an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, all of the groups may be unsubstituted or substituted with one halogen atom or two or more of halogen atoms, and the cyclic group may include one or more of F, Cl, CF 3 , OCF 3 , a CN group, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkanoyl group having 1 to 8 carbon atoms, an alkanoyloxy group having 1 to 8 carbon atoms, an alkoxycarbonyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkenyloxy group having 2 to 8 carbon atoms, an alkenoyl group having 2 to 8 carbon atoms, or an alkenoyloxy group having 2 to 8 carbon atoms, as a substituent.
m4 to m9 each independently represent an integer of 0 to 18, and n4 to n9 each independently represent 0 or 1.
One kind or two or more kinds of the multifunctional polymerizable liquid crystal compound including three or more of polymerizable functional groups can be used.
The total content of the multifunctional polymerizable liquid crystal compound including three or more of polymerizable functional groups in a molecule is preferably 0% to 80% by mass, more preferably 0% to 60% by mass, and particularly preferably 0% to 40% by mass, with respect to total amount of the compound represented by General Formula (II) used. In a case of significantly considering rigidity of an optically anisotropic body, the lower limit value is preferably equal to or greater than 10% by mass, more preferably equal to or greater than 20% by mass, and particularly preferably equal to or greater than 30% by mass. Meanwhile, in a case of significantly considering low curing shrinkage, the upper limit value is preferably equal to or smaller than 50% by mass, more preferably equal to or smaller than 35% by mass, and particularly preferably equal to or smaller than 20% by mass.
(Use of Plurality of Kinds of Polymerizable Liquid Crystal Compounds)
In the polymerizable liquid crystal composition of the present invention, a plurality of kinds of the polymerizable liquid crystal compounds are preferably mixed with each other and used. It is preferable that at least one kind or more of monofunctional polymerizable liquid crystal compound, at least one kind or more of bifunctional polymerizable liquid crystal compound, and/or multifunctional polymerizable liquid crystal compound are used in combination, because hardenability of an optically anisotropic body to be obtained is improved and excellent adhesiveness with a base material is obtained. It is more preferable that at least one kind or more of monofunctional polymerizable liquid crystal compound and at least one kind or more of bifunctional polymerizable liquid crystal compound are used in combination. Among these, when an optically anisotropic body is obtained by using the polymerizable liquid crystal composition of the present invention, in a case of further improving hardenability, as the bifunctional polymerizable liquid crystal compound, it is preferable to obtain a mixture of the polymerizable liquid crystal compounds by using the compound selected from (II-2-2-1) to (II-2-2-2) including two or three ring structures in the compound, and it is particularly preferable to obtain a mixture in which the compound represented by (II-2-1-1) and (II-2-2-1) including two ring structures are used in the compound in combination.
The total amount of the monofunctional polymerizable liquid crystal compound and the bifunctional polymerizable liquid crystal compound is preferably 70% by mass to 100% by mass and particularly preferably 80% by mass to 100% by mass, with respect to the total amount of the compound represented by General Formula (II) used.
The total content of the compound represented by General Formula (II) is preferably 5% to 90% by mass, more preferably 5% to 70% by mass, and particularly preferably 5% to 40% by mass, with respect to total amount of the polymerizable compound used in the polymerizable composition (that is, the total content of the reverse dispersible compound represented by General Formula (I) and the total content of the compound represented by General Formula (II)).
(Other Liquid Crystal Compounds)
In addition, a compound including a mesogenic group not including a polymerizable group may be added to the liquid crystal composition of the present invention, and compounds used in typical liquid crystal devices, for example, supertwisted nematic (STN) liquid crystal, twisted nematic (TN) liquid crystal, or thin film transistor (TFT) liquid crystal, are used.
Specifically, the compound including a mesogenic group not including a polymerizable functional group is preferably a compound represented by General Formula (5).
[Chem. 227]
R 51 -MG3-R 52 (5)
A mesogenic group represented by MG3 or mesogenic support group is a compound represented by General Formula (5-b).
[Chem. 228]
—Z0 d -(A1 d -Z1 d ) ne -A2 d -Z2 d -A3 d -Z3 d - (5-b)
(In the formula, A1 d , A2 d , and A3 d each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a 1,4-cyclohexenyl group, a tetrahydropyran-2,5-diyl group, a 1,3-dioxane-2,5-diyl group, a tetrahydrothiopyran-2,5-diyl group, a 1,4-bicyclo (2,2,2) octylene group, a decahydronaphthalene-2,6-diyl group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a pyrazine-2,5-diyl group, a thiophene-2,5-diyl group-, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a 2,6-naphthylene group, a phenanthrene-2,7-diyl group, a 9,10-dihydrophenanthrene-2,7-diyl group, a 1,2,3,4,4a,9,10a-octahydrophenanthrene-2,7-diyl group, a 1,4-naphthylene group, a benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl group, a benzo[1,2-b:4,5-b′]diselenophene-2,6-diyl group, a [I]benzothieno[3,2-b]thiophene-2,7-diyl group, a [1]benzoselenopheno[3,2-b] selenophene-2,7-diyl group, or a fluorene-2,7-diyl group. As a substituent, one or more of F, Cl, CF 3 , OCF 3 , a CN group, an alkyl group, an alkoxy group, an alkanoyl group, or an alkanoyloxy group having 1 to 8 carbon atoms, an alkenyl group, an alkenyloxy group, an alkenoyl group, or an alkenoyloxy group having 2 to 8 carbon atoms. Z0 d , Z1 d , Z2 d , and Z3 d each independently represent —COO—, —OCO—, —CH 2 CH 2 —, —OCH 2 —, —CH 2 O—, —CH═CH—, —C≡C—, —CH═CHCOO—, —OCOCH═CH—, —CH 2 CH 2 COO—, —CH 2 CH 2 OCO—, —COOCH 2 CH 2 —, —OCOCH 2 CH 2 —, —CONH—, —NHCO—, an alkylene group having 2 to 10 carbon atoms which may include a halogen atoms, or a single bond. n e represents 0, 1, or 2, R 51 and R 52 each independently represent a hydrogen atom, a halogen atom, a cyano group, or an alkyl group having 1 to 18 carbon atoms, the alkyl group may be substituted with one or more of halogen atoms or CN, and one CH 2 group or two or more of (—CH 2 —)'s that are not adjacent to each other present in this group may be each mutually independently substituted with —O—, —S—, —NH—, —N(CH 3 )—, —CO—, —COO—, —OCO—, —OCOO—, —SCO—, —COS—, or —C≡C—, in a state where oxygen atoms are not directly bonded to each other.)
Specifically, the following examples are shown, but there is no limitation.
Ra and Rb each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkenyl group having 1 to 6 carbon atoms, a cyano group. In a case where these groups are an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, all of the groups may be unsubstituted or substituted with one halogen atom or two or more of halogen atoms.
The total content of the compound including a mesogenic group is preferably 0% by mass to 20% by mass, with respect to the total amount of the total content of the reverse dispersible compound represented by General Formula (I) and the total content of the compound represented by General Formula (II). In a case of use, the total content is preferably equal to or greater than 1% by mass, preferably equal to or greater than 2% by mass, and preferably equal to or greater than 5% by mass, and preferably equal to or smaller than 15% by mass, and preferably equal to or smaller than 10% by mass.
(Other Components)
(Chiral Compound)
The polymerizable liquid crystal composition of the present invention can also include a polymerizable chiral compound which may exhibit liquid crystal properties or may be amorphous, in addition to the polymerizable compound represented by General Formula (II).
The polymerizable chiral compound used in the present invention preferably includes one or more of polymerizable functional groups. Examples of such a compound include a polymerizable chiral compound including chiral saccharide such as isosorbide, isomannit, or glucoside, a rigid part such as 1,4-phenylene group or 1,4-cyclohexylene group, and a polymerizable functional group such as a vinyl group, an acryloyl group, a (meth)acryloyl group, or a maleimide group, disclosed in JP-A-H11-193287, JP-A-2001-158788, JP-T-2006-52669, JP-A-2007-269639, JP-A-2007-269640, and JP-A-2009-84178, a polymerizable chiral compound formed of a terpenoid derivative, disclosed in JP-A-H8-239666, a polymerizable chiral compound formed of a mesogenic group and a spacer including a chiral part, disclosed in NATURE Vol. 35, pp. 467-469 (published 30, November 1995), and NATURE Vol. 392, pp. 476-479 (published 2, April, 1998), or a polymerizable chiral compound including a binaphthyl group disclosed in JP-T-2004-504285 and JP-A-2007-248945. Among these, a chiral compound having a great helical twisting power (HTP) is preferably used in the polymerizable liquid crystal composition of the present invention.
It is necessary that a blending amount of the polymerizable chiral compound is suitably adjusted in accordance with a helical induction power of the compound, and the blending amount is preferably 0% to 25% by mass, more preferably 0% to 20% by mass, and particularly preferably 0% to 15% by mass, with respect to the total amount of the total content of the reverse dispersible compound represented by General Formula (I) and the total content of the compound represented by General Formula (II).
As one example of General Formula of the polymerizable chiral compound, General Formulae (3-1) to (3-4) can be used, but there is no limitation to the general formulae.
In the formulae, SP 3a and SP 3b each independently represent an alkylene group having 0 to 18 carbon atoms, the alkylene group may be substituted with one or more of halogen atoms, a CN group, or an alkyl group having 1 to 8 carbon atoms including a polymerizable functional group, and one CH 2 group or two or more of (—CH 2 —)'s CH 2 groups that are not adjacent to each other present in this group may be each mutually independently substituted with —O—, —S—, —NH—, —N(CH 3 )—, —CO—, —COO—, —OCO—, —OCOO—, —SCO—, —COS—, or —C≡C—, in a state where oxygen atoms are not directly bonded to each other. A1, A2, A3, A4, and A5 each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a 1,4-cyclohexenyl group, a tetrahydropyran-2,5-diyl group, a 1,3-dioxane-2,5-diyl group, a tetrahydrothiopyran-2,5-diyl group, a 1,4-bicyclo (2,2,2) octylene group, a decahydronaphthalene-2,6-diyl group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a pyrazine-2,5-diyl group, a thiophene-2,5-diyl group-, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a 2,6-naphthylene group, a phenanthrene-2,7-diyl group, a 9,10-dihydrophenanthrene-2,7-diyl group, a 1,2,3,4,4a,9,10a-octahydrophenanthrene-2,7-diyl group, a 1,4-naphthylene group, a benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl group, a benzo[1,2-b:4,5-b′]diselenophene-2,6-diyl group, a [1]benzothieno[3,2-b]thiophene-2,7-diyl group, a [1]benzoselenopheno[3,2-b]selenophene-2,7-diyl group, or a fluorene-2, 7-diyl group. n, 1, k each independently represent 0 or 1, a relationship of 0<n+1+k<3 is satisfied. Z0, Z1, Z2, Z3, Z4, Z5, and Z6 each independently represent —COO—, —OCO—, —CH 2 CH 2 —, —OCH 2 —, —CH 2 O—, —CH═CH—, —C≡C—, —CH═CHCOO—, —OCOCH═CH—, —CH 2 CH 2 COO—, —CH 2 CH 2 OCO—, —COOCH 2 CH 2 —, —OCOCH 2 CH 2 —, —CONH—, —NHCO—, an alkyl group having 2 to 10 carbon atoms which may include a halogen atom, or a single bond. n5 and m5 each independently represent 0 or 1, R 3a and R 3b represent a hydrogen atom, a halogen atom, a cyano group, or an alkyl group having 1 to 18 carbon atoms, the alkyl group may be substituted with one or more of halogen atoms or CN, and one CH 2 group or two or more of (—CH 2 —)'s that are not adjacent to each other present in this group may be each mutually independently substituted with —O—, —S—, —NH—, —N(CH 3 )—, —CO—, —COO—, —OCO—, —OCOO—, —SCO—, —COS—, or —C≡C—, in a state where oxygen atoms are not directly bonded to each other. Alternatively, R 3a and R 3b preferably represent General Formula (3-a).
[Chem. 232]
—P 3a (3-a)
(In the formula, R 3a represents a polymerizable functional group and SP 3a represents the same meaning as SP 1 .)
P 3a preferably represents a substituent selected from a polymerizable group represented by Formula (P-1) to Formula (P-20).
Among these polymerizable functional groups, from a viewpoint of increasing polymerizability and storage stability, Formula (P-1), (P-2), (P-7), (P-12), or (P-13) is preferable, and Formula (P-1), (P-7), or (P-12) is more preferable.
As specific examples of the polymerizable chiral compound, compounds of Compounds (3-5) to (3-25) can be used, but there is no limitation to the following compounds.
In the formulae, m, n, k, and l each independently represent an integer of 1 to 18, and R 1 to R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a carboxyl group, or a cyano group. In a case where these groups are an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, all of the groups may be unsubstituted or substituted with one halogen atom or two or more of halogen atoms.
(Polymerizable Discotic Compound)
The polymerizable liquid crystal composition of the present invention can also include a polymerizable discotic compound which may exhibit liquid crystal properties or may be amorphous, in addition to the polymerizable compound represented by General Formula (II).
The polymerizable discotic compound used in the present invention preferably includes one or more of polymerizable functional groups. Examples of such a compound include a polymerizable compound disclosed in JP-A-H7-281028, JP-A-H7-287120, JP-A-H7-333431, and JP-A-H8-27284.
It is necessary that a blending amount of the polymerizable discotic compound is suitably adjusted in accordance with the compound, and the blending amount is preferably 0% to 10% by mass in the polymerizable liquid crystal composition.
As one example of General Formula of the polymerizable discotic compound, General Formulae (4-1) to (4-3) can be used, but there is no limitation to the general formulae.
In the formulae, SP 4 represents an alkylene group having 0 to 18 carbon atoms, the alkylene group may be substituted with one or more of halogen atoms, a CN group, or an alkyl group having 1 to 8 carbon atoms including a polymerizable functional group, and one CH 2 group or two or more of (—CH 2 —)'s that are not adjacent to each other present in this group may be each mutually independently substituted with —O—, —S—, —NH—, —N(CH 3 )—, —CO—, —COO—, —OCO—, —OCOO—, —SCO—, —COS—, or —C≡C—, in a state where oxygen atoms are not directly bonded to each other. A 4 represents a 1,4-phenylene group, a 1,4-cyclohexylene group, a 1,4-cyclohexenyl group, a tetrahydropyran-2,5-diyl group, a 1,3-dioxane-2,5-diyl group, a tetrahydrothiopyran-2,5-diyl group, a 1,4-bicyclo (2,2,2) octylene group, a decahydronaphthalene-2,6-diyl group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a pyrazine-2,5-diyl group, a thiophene-2,5-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a 2,6-naphthylene group, a phenanthrene-2,7-diyl group, a 9,10-dihydrophenanthrene-2,7-diyl group, a 1,2,3,4,4a,9,10a-octahydrophenanthrene-2,7-diyl group, a 1,4-naphthylene group, a benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl group, a benzo[1,2-b:4,5-b′]diselenophene-2,6-diyl group, a [1]benzothieno[3,2-b]thiophene-2,7-diyl group, a [1]benzoselenopheno[3,2-b]selenophene-2,7-diyl group, or a fluorene-2,7-diyl group. n5 represents 0 or 1, Z 4 a represents —CO—, —CH 2 CH 2 —, —CH 2 O—, —CH═CH—, —CH═CHCOO—, —CH 2 CH 2 COO—, —CH 2 CH 2 OCO—, —COCH 2 CH 2 —, an alkyl group having 2 to 10 carbon atoms which may include a halogen atom, or a single bond. Z 4b represents —COO—, —OCO—, —OCH 2 —, —CH 2 O—, —CH═CH—, —C≡C—, —CH═CHCOO—, —OCOCH═CH—, —CH 2 CH 2 COO—, —CH 2 CH 2 OCO—, —COOCH 2 CH 2 —, —OCOCH 2 CH 2 —, —CONH—, —NHCO—, —OCOO—, an alkyl group having 2 to 10 carbon atoms which may include a halogen atom, or a single bond. R 4 represents a hydrogen atom, a halogen atom, a cyano group, or an alkyl group having 1 to 18 carbon atoms, the alkyl group may be substituted with one or more of halogen atoms or CN, and one CH 2 group or two or more of (—CH 2 —)'s that are not adjacent to each other present in this group may be each mutually independently substituted with —O—, —S—, —NH—, —N(CH 3 )—, —CO—, —COO—, —OCO—, —OCOO—, —SCO—, —COS—, or —C≡C—, in a state where oxygen atoms are not directly bonded to each other. Alternatively, R 4 preferably represents General Formula (4-a).
[Chem. 239]
—P 4a (4-a)
(In the formula, P 4a represents a polymerizable functional group and SP 3a represents the same meaning as Sp 1 .)
P 4a preferably represents a substituent selected from a polymerizable group represented by Formula (P-1) to Formula (P-20).
Among these polymerizable functional groups, from a viewpoint of increasing polymerizability and storage stability, Formula (P-1), (P-2), (P-7), (P-12), or (P-13) is preferable, and Formula (P-1), (P-7), or (P-12) is more preferable.
As specific examples of the polymerizable discotic compound, compounds of Compounds (4-4) to (4-8) can be used, but there is no limitation to the following compounds.
In the formulae, n represents an integer of 1 to 18.
(Organic Solvent)
An organic solvent may be added to the polymerizable liquid crystal composition of the present invention. The organic solvent used is not particularly limited, and is preferably an organic solvent in which the polymerizable liquid crystal compound exhibits excellent solubility, and preferably an organic solvent which can be dried at a temperature equal to or lower than 100° C. Examples of such a solvent include aromatic hydrocarbon such as toluene, xylene, cumene, or mesitylene, an ester-based solvent such as methyl acetate, ethyl acetate, propyl acetate, or butyl acetate, a ketone-based solvent such as methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, or cyclopentanone, an ether-based solvent such as tetrahydrofuran, 1,2-dimethoxy ethane, or anisole, an amide-based solvent such as N,N-dimethylformamide or N-methyl-2-pyrrolidone, propylene glycol monomethyl ether acetate, diethylene glycol monomethyl ether acetate, γ-butyrolactone, and chlorobenzene. These can be used alone or in combination of two or more kinds thereof, and it is preferable to use any one or more kinds from a ketone-based solvent, an ether-based solvent, an ester-based solvent, and an aromatic hydrocarbon-based solvent from a viewpoint of solution stability.
When the organic solvent is used as a solution, the composition used in the present invention can be applied to a substrate. A percentage of the organic solvent used in the polymerizable liquid crystal composition is not particularly limited, as long as it does not significantly damage the coated state, and the total amount of the organic solvent included in the polymerizable liquid crystal composition is preferably 10% to 95% by mass, more preferably 12% to 90% by mass, and particularly preferably 15% to 85% by mass.
When dissolving the polymerizable liquid crystal composition in the organic solvent, it is preferable to perform heating and stirring, in order to evenly dissolve the polymerizable liquid crystal composition. A heating temperature at the time of the heating and stirring may be suitably adjusted, by considering solubility of the composition used in the organic solvent, and is preferably 15° C. to 110C, more preferably 15° C. to 105° C., even more preferably 15° C. to 100° C., and particularly preferably 20° C. to 90° C., from a viewpoint of productivity.
In addition, when adding a solvent, it is preferable that stirring and mixing are performed by a dispersing stirrer. Specifically, as the dispersing stirrer, a disper, a propeller, a dispersing device including a stirring blade such as turbine blade, a paint shaker, a planetary stirring device, a shaker, or a rotary evaporator can be used. In addition, an ultrasonic irradiation device can be used.
A stirring rotation rate when adding a solvent is preferably suitably adjusted by a stirring device used, and the stirring rotation rate is preferably 10 rpm to 1,000 rpm, more preferably 50 rpm to 800 rpm, and particularly preferably 150 rpm to 600 rpm, in order to obtain an even polymerizable liquid crystal composition solvent.
(Polymerization Inhibitor)
A polymerization inhibitor is preferably added to the polymerizable liquid crystal composition of the present invention. Examples of the polymerization inhibitor include a phenol-based compound, a quinone-based compound, an amine-based compound, a thioether-based compound, and a nitroso compound.
Examples of the phenol-based compound include p-methoxyphenol, cresol, t-butylcatechol, 3.5-di-t-butyl-4-hydroxytoluene, 2.2′-methylene bis(4-methyl-6-t-butylphenol), 2.2′-methylene bis(4-ethyl-6-t-butylphenol), 4.4′-thio bis(3-methyl-6-t-butylphenol), 4-methoxy-1-naphthol, and 4,4′-dialkoxy-2,2′-bi-1-naphthol.
Examples of quinone-based compound include hydroquinone, methylhydroquinone, tert-butylhydroquinone, p-benzoquinone, methyl-p-benzoquinone, tert-butyl-p-benzoquinone, 2,5-diphenylbenzoquinone, 2-hydroxy-1,4-naphthoquinone, 1,4-naphthoquinone, 2,3-dichloro-1,4-naphthoquinone, anthraquinone, and diphenoquinone.
Examples of the amine-based compound include p-phenylenediamine, 4-aminodiphenylamine, N.N′-diphenyl-p-phenylenediamine, N-i-propyl-N′-phenyl-p-phenylenediamine, N-(1.3-dimethylbutyl)-N′-phenyl-p-phenylenediamine, N.N′-di-2-naphthyl-p-phenylenediamine, diphenylamine, N-phenyl-β-naphthylamine, 4.4′-dicumyl-diphenylamine, and 4.4′-dioctyl-diphenylamine.
Examples of the thioether-based compound include phenothiazine and distearyl thiodipropionate.
Examples of the nitroso compound include N-nitrosodiphenylamine, N-nitrosophenylnaphthylamine, N-nitrosodinaphthylamine, p-nitrosophenol, nitrosobenzene, p-nitrosodiphenylamine, α-nitroso-β-naphthols, N,N-dimethyl p-nitrosoaniline, p-nitrosodiphenylamine, p-nitrone dimethylamine, p-nitrone-N, N-diethylamine, N-nitrosoethanolamine, N-nitrosodi-n-butylamine, N-nitroso-N-n-butyl-4-butanolamine, N-nitroso-diisopropanolamine, N-nitroso-N-ethyl-4-butanolamine, 5-nitroso-8-hydroxyquinoline, N-nitrosomorpholine, N-nitroso N-phenylhydroxylamine ammonium salt, nitrosobenzene, 2,4,6-tri-tert-butylnitrone benzene, N-nitroso-N-methyl-p-toluenesulfonamide, N-nitroso-N-ethylurethane, N-nitroso-N-n-propylurethane, 1-nitroso-2-naphthol, 2-nitroso-l-naphthol, sodium 1-nitroso-2-naphthol-3,6-sulfonate, sodium 2-nitroso-l-naphthol-4-sulfonate, 2-nitroso-5-methylaminophenol hydrochloride, and 2-nitroso-5-methylaminophenol hydrochloride.
The amount of the polymerization inhibitor added is preferably 0.01% to 1.0% by mass and more preferably 0.05% to 0.5% by mass with respect to the polymerizable liquid crystal composition.
(Antioxidant)
In order to increase stability of the polymerizable liquid crystal composition of the present invention, it is preferable to add an antioxidant. Examples of such compounds include a hydroquinone derivative, a nitrosamine-based polymerization inhibitor, and a hindered phenol-based antioxidant, and more specific examples thereof include tert-butylhydroquinone, methylhydroquinone, “Q-1300” and “Q-1301” manufactured by Wako Pure Chemical Industries, Ltd., “IRGANOX1010”, “IRGANOX1035”, “IRGANOX1076”, “IRGANOX1098”, “IRGANOX1135”, “IRGANOX1330”, “IRGANOX1425”, “IRGANOX1520”, “IRGANOX1726”, “IRGANOX245”, “IRGANOX259”, “IRGANOX3114”, “IRGANOX3790”, “IRGANOX5057”, or “IRGANOX565” manufactured by BASF.
The amount of the antioxidant added is preferably 0.01% to 2.0% by mass and more preferably 0.05% to 1.0% by mass with respect to the polymerizable liquid crystal composition.
(Photopolymerization Initiator)
The polymerizable liquid crystal composition of the present invention preferably includes a photopolymerization initiator. It is preferable that at least one or more kinds of the photopolymerization initiator are included. Specific examples thereof include “Irgacure 651”, “Irgacure 184”, “Irgacure 907”, “Irgacure 127”, “Irgacure 369”, “Irgacure 379”, “Irgacure 819”, “Irgacure 2959”, “Irgacure 1800”, “Irgacure 250”, “Irgacure 754”, “Irgacure 784”, “Irgacure OXE01”, “Irgacure OXE02”, “Lucirin TPO”, “Darocur 1173”, “Darocur MBF” manufactured by BASF, “Esacure 1001M”, “Esacure KIP150”, “Speedcure BEM”, “Speedcure BMS”, “Speedcure MBP”, “Speedcure PBZ”, “Speedcure ITX”, “Speedcure DETX”, “Speedcure EBD”, “Speedcure MBB”, “Speedcure BP” manufactured by LAMBSON, “KAYACURE DMBI” by Nippon Kayaku Co., Ltd., “TAZ-A” manufactured by DKSH, “ADEKA OPTOMER SP-152”, “ADEKA OPTOMER SP-170”, “ADEKA OPTOMER N-1414”, “ADEKA OPTOMER N-1606”, “ADEKA OPTOMER N-1717”, and “ADEKA OPTOMER N-1919” manufactured by ADEKA Corporation.
The amount of the photopolymerization initiator used is preferably 0.1% to 10% by mass and particularly preferably 0.5% to 7% by mass with respect to the polymerizable liquid crystal composition. These can be used alone or in combination of two or more kinds thereof, and a sensitizer or the like may be added thereto.
(Thermal Polymerization Initiator)
In the polymerizable liquid crystal composition of the present invention, a thermal polymerization initiator may be used in combination with the photopolymerization initiator. Specific examples thereof include “V-40” and “VF-096” manufactured by Wako Pure Chemical Industries, Ltd., and “PERHEXYL D” and “PERHEXYL I” manufactured by NOF Corporation.
The amount of thermal polymerization initiator used is preferably 0.1% to 10% by mass and particularly preferably 0.5% to 5% by mass with respect to the polymerizable liquid crystal composition. These can be used alone or in combination of two or more kinds thereof.
(Surfactant)
The polymerizable liquid crystal composition of the present invention may include at least one or more kinds of surfactants, in order to decrease unevenness of film thickness, in a case where an optically anisotropic body is prepared. Examples of surfactant which can be included include alkyl carboxylate, alkyl phosphate, alkyl sulfonate, fluoroalkyl carboxylate, fluoroalkyl phosphate, fluoroalkyl sulfonate, a polyoxyethylene derivative, a fluoroalkyl ethylene oxide derivative, a polyethylene glycol derivative, an alkyl ammonium salt, and a fluoroalkyl ammonium salt, and a fluorosurfactant is particularly preferable.
Specific examples thereof include “MEGAFACE F-251”, MEGAFACE F-444”, “MEGAFACE F-477”, “MEGAFACE F-510”, “MEGAFACE F-552”, “MEGAFACE F-553”, “MEGAFACE F-554”, “MEGAFACE F-555”, “MEGAFACE F-556”, “MEGAFACE F-557” “MEGAFACE F-558”, “MEGAFACE F-559”, “MEGAFACE F-560”, “MEGAFACE F-561”, “MEGAFACE F-562”, “MEGAFACE F-563”, “MEGAFACE F-565”, “MEGAFACE F-567”, “MEGAFACE F-568”, “MEGAFACE F-569”, “MEGAFACE F-570”, “MEGAFACE F-571”, “MEGAFACE R-40”, “MEGAFACE R-41”, “MEGAFACE R43”, “MEGAFACE R94”, “MEGAFACE RS-72-K”, “MEGAFACE RS-75”, “MEGAFACE RS-76-E”, “MEGAFACE RS-90” (all manufactured by DIC Corporation), “FTERGENT 100”, “FTERGENT 100C”, “FTERGENT 110”, “FTERGENT 150”, “FTERGENT 150CH”, “FTERGENT A”, “FTERGENT 100A-K”, “FTERGENT 501”, “FTERGENT 300”, “FTERGENT 310”, “FTERGENT 320”, “FTERGENT 400SW”, “FTX-400P”, “FTERGENT 251”, “FTERGENT 215M”, “FTERGENT 212MH”, “FTERGENT 250”, “FTERGENT 222F”, “FTERGENT 212D”, “FTX-218”, “FTX-209F”, “FTX-213F”, “FTX-233F”, “FTERGENT 245F”, “FTX-208G”, “FTX-240G”, “FTX-206D”, “FTX-220D”, “FTX-230D”, “FTX-240D”, “FTX-207S”, “FTX-211S”, “FTX-220S”, “FTX-230S”, “FTX-750FM”, “FTX-730FM”, “FTX-730FL”, “FTX-710FS”, “FTX-710FM”, “FTX-710FL”, “FTX-750LL”, “FTX-730LS”, “FTX-730LM”, “FTX-730LL”, “FTX-710LL” (all manufactured by Neos Company Limited), “BYK-300”, “BYK-302”, “BYK-306”, “BYK-307”, “BYK-310”, “BYK-315”, “BYK-320”, “BYK-322”, “BYK-323”, “BYK-325”, “BYK-330”, “BYK-331”, “BYK-333”, “BYK-337”, “BYK-340”, “BYK-344”, “BYK-3440”, “BYK-370”, “BYK-375”, “BYK-377”, “BYK-350”, “BYK-352”, “BYK-354”, “BYK-355”, “BYK-356”, “BYK-358N”, “BYK-361N”, “BYK-357”, “BYK-390”, “BYK-392”, “BYK-UV3500”, “BYK-UV3510”, “BYK-UV3570”, “BYK-Silclean3700” (all manufactured by BYK), “TEGO Rad2100”, “TEGO Rad2200N”, “TEGO Rad2250”, “TEGO Rad2300”, “TEGO Rad2500”, “TEGO Rad2600”, “TEGO Rad2700” (all manufactured by TOMOE Engineering Co., Ltd.), “N215”, “N535”, “N605K”, and “N935” (all manufactured by Solvay).
The amount of surfactant used is preferably 0.01% to 2% by mass and particularly preferably 0.05% to 0.5% by mass with respect to the polymerizable liquid crystal composition.
In addition, by using the surfactant, in a case where an optically anisotropic body is obtained by using the polymerizable liquid crystal composition of the invention, it is possible to effectively decrease the tilt angle of the air interface and by suitably selecting the surfactant, it is also possible to control the tilt angle.
In the polymerizable liquid crystal composition of the present invention, a compound including a repeating unit represented by General Formula (7) and having a weight average molecular weight equal to or greater than 100 is used, as a compound other than the surfactant exhibiting an effect of effectively decreasing the tilt angle of the air interface, in a case where an optically anisotropic body is obtained.
[Chem. 244]
CR 11 R 12 —CR 13 R 14 (7)
In the formula, R 11 , R 12 , R 13 , and R 14 each independently represent a hydrogen atom, a halogen atom, or a hydrocarbon group having 1 to 20 carbon atoms, and hydrogen atoms in the hydrocarbon group may be substituted with one or more of halogen atoms.
Examples of a suitable compound represented by General Formula (7) include polyethylene, polypropylene, polyisobutylene, paraffin, liquid paraffin, chlorinated polypropylene, chlorinated paraffin, and chlorinated liquid paraffin.
The amount of the compound represented by General Formula (7) added is preferably 0.01% to 1% by mass and more preferably 0.05% to 0.5% by mass with respect to the polymerizable liquid crystal composition.
(Curing Agent)
In the polymerizable liquid crystal composition of the present invention, a curing agent may be used. Specific examples thereof include aliphatic polyamine such as diethylenetriamine or triethylenetetramine, EH-235R-2 manufactured by ADEKA Corporation, and a ketimine compound such as jERCURE H3, H30 manufactured by Mitsubishi Chemical Corporation.
The amount of curing agent used is preferably 0.01% to 20% by mass, more preferably 0.05% to 15% by mass, and particularly preferably 0.1% to 10% by mass, with respect to the polymerizable liquid crystal composition. These can be used alone or in combination of two or more kinds thereof.
(Other Additives)
In addition, for adjusting physical properties, if necessary, additives such as amorphous polymerizable compound, a thixotropic agent, an ultraviolet absorber, an infrared absorber, an antioxidant, or a surface treatment agent can be added to some extent that alignment of liquid crystals is not significantly decreased.
(Manufacturing Method of Optically Anisotropic Body)
(Optically Anisotropic Body)
The optically anisotropic body of the present invention prepared by using the polymerizable liquid crystal composition of the present invention is a component obtained by laminating a base material, an alignment film, if necessary, and a polymer of the polymerizable liquid crystal composition, in this order.
(Base Material)
The base material used in the optically anisotropic body of the present invention is a base material which is generally used in a liquid crystal device, a display, an optical component, or an optical film, and is not particularly limited, as long as it is a material having heat resistance so as to withstand the heating at the time of drying after applying the polymerizable liquid crystal composition of the present invention. As the base material, an organic material such as a glass base material, a metal base material, a ceramic base material, or a plastic base material is used. Particularly, in a case where the base material is an organic material, examples thereof include a cellulose derivative, polyolefin, polyester, polycarbonate, polyacrylate (acrylic resin), polyarylate, polyether sulfone, polyimide, polyphenylene sulfide, polyphenylene ether, nylon, and polystyrene. Among these, a plastic base material such as polyester, polystyrene, polyacrylate, polyolefin, a cellulose derivative, polyarylate, or polycarbonate is preferable, and a base material such as polyacrylate, polyolefin, or a cellulose derivative is more preferable. It is particularly preferable that a cycloolefin polymer (COP) is used as polyolefin, triacetyl cellulose (TAC) is used as a cellulose derivative, and polymethyl methacrylate (PMMA) is used as polyacrylate. The shape of the base material may have a curved surface, in addition to a flat plate. These base materials may include an electrode layer and has an antireflection function or reflection function, if necessary.
The surface treatment of these base materials may be performed, in order to improve coating properties or adhesiveness of the polymerizable liquid crystal composition of the present invention. As the surface treatment, ozone treatment, plasma treatment, corona treatment, silane coupling treatment, and the like are used. In addition, in order to adjust transmittance or reflectance of light, an organic thin film, an inorganic oxide thin film, or a metal thin film may be provided on the surface of the base material by vapor deposition, or in order to provide an optically added value, the base material may be a pickup lens, a rod lens, an optical disk, a retardation film, a light diffusing film, or a color filter. Among these, a pickup lens, a retardation film, a light diffusing film, and a color filter are preferable so as to further increase the added value.
(Alignment Treatment)
The base material is generally subjected to alignment treatment or an aligned film may be provided thereon, in order to allow the polymerizable liquid crystal composition to be aligned when the polymerizable liquid crystal composition of the present invention is applied and dried. Examples of the alignment treatment include stretching treatment, rubbing treatment, polarized light ultraviolet-visible light irradiation treatment, and ion beam treatment. In a case of using an aligned film, a commonly used well-known aligned film is used. Examples of such an aligned film include compounds such as polyimide, polysiloxane, polyamide, polyvinyl alcohol, polycarbonate, polystyrene, polyphenylene ether, polyarylate, polyethylene terephthalate, polyether sulfone, an epoxy resin, an epoxyacrylate resin, an acrylic resin, a coumarin compound, a chalcone compound, a cinnamate compound, a fulgide compound, an anthraquinone compound, an azo compound, and an arylethene compound. As a compound to be subjected to the alignment treatment by rubbing, it is preferable to use a compound in which crystallization of the material is promoted by the alignment treatment or by adding a heating step after the alignment treatment. Among compounds to be subjected to the alignment treatment other than the rubbing, it is preferable to use a photo-alignment material.
(Coating)
Examples of the coating method for obtaining the optically anisotropic body of the present invention include well-known commonly used methods such as an applicator method, a bar coating method, a spin-coating method, a roll coating method, a direct gravure coating method, a reverse gravure coating method, a flexographic coating method, an ink jet method, a die coating method, a cap coating method, a dip coating method, and a slit coating method. The polymerizable liquid crystal composition is coated and then dried, if necessary.
(Polymerization Step)
The polymerization treatment of the polymerizable liquid crystal composition of the present invention, is generally performed by light irradiation such as ultraviolet light or heating in a state where the liquid crystal compounds in the polymerizable liquid crystal composition are subjected to horizontal alignment, vertical alignment, or hybrid alignment, or cholesteric alignment (plane alignment) with respect to the base material. In a case of performing the polymerization by light irradiation, specifically, it is preferable to emit ultraviolet light having a wavelength equal to or smaller than 390 nm and it is most preferable to emit light having a wavelength of 250 to 370 nm. However, in a case where the polymerizable liquid crystal composition causes decomposition or the like due to the ultraviolet light having a wavelength equal to or smaller than 390 nm, the polymerizable treatment may be preferably performed with ultraviolet light having a wavelength equal to or greater than 390 nm. This light is preferably diffuse light and unpolarized light.
(Polymerization Method)
A method of emitting active energy rays or a thermal polymerization method is used as a method of polymerizing the polymerizable liquid crystal composition of the present invention, but the method of emitting active energy rays is preferable, because the reaction proceeds at room temperature without the necessities of the heating, and among the methods, a method of emitting light such as ultraviolet rays is preferable, from a viewpoint of a simple operation.
It is preferable that a temperature at the time of emission is set as a temperature at which the polymerizable liquid crystal composition of the present invention can maintain the liquid crystal phase and is equal to or lower than 30° C. as possible, in order to avoid evocation of the thermal polymerization of the polymerizable liquid crystal composition. The liquid crystal composition generally shows liquid crystal phases at a C(solid phase)-N(nematic) transition temperature (hereinafter, abbreviated as a C—N transition temperature) to the N—I transition temperature in the heating process. Meanwhile, in the cooling process, the liquid crystal state may be maintained even at a temperature equal to or lower than the C—N transition temperature, without performing solidification, in order to acquire a thermodynamically nonequilibrium state. This state is called a supercooled state. In the present invention, the liquid crystal composition in the supercooled state is also included as the liquid crystal composition maintaining the liquid crystal phase. Specifically, it is preferable to emit ultraviolet light having a wavelength equal to or smaller than 390 nm and it is most preferable to emit light having a wavelength of 250 to 370 nm. However, in a case where the polymerizable composition causes decomposition or the like due to the ultraviolet light having a wavelength equal to or smaller than 390 nm, the polymerizable treatment may be preferably performed with ultraviolet light having a wavelength equal to or greater than 390 nm. This light is preferably diffuse light and unpolarized light. Ultraviolet light irradiation intensity is preferably 0.05 kW/m 2 to 10 kW/m 2 . The ultraviolet light irradiation intensity is particularly preferably 0.2 kW/m 2 to 2 kW/m 2 . When the ultraviolet light intensity is less than 0.05 kW/m 2 , a considerable time is taken for completing the polymerization. Meanwhile, in a case of the intensity exceeding 2 kW/m 2 , photolysis of the liquid crystal molecules in the polymerizable liquid crystal composition tends to occur, or the temperature during the polymerization may be increased due to generation of a considerable amount of heat of polymerization, an order parameter of the polymerizable liquid crystals may change, and the disorder may occur in the retardation of the polymerized film.
When a specific portion is only polymerized by the ultraviolet light irradiation using a mask, then, the alignment state of the unpolymerized portion is changed by applying an electric filed, a magnetic field, or a temperature, and then, the unpolymerized portion is polymerized, it is possible to obtain an optically anisotropic body having a plurality of regions having different alignment directions.
In addition, it is also possible to obtain an optically anisotropic body having a plurality of regions having different alignment directions, by regulating the alignment by applying an electric filed, a magnetic field, or a temperature to the polymerizable liquid crystal composition in the unpolymerized state in advance, when polymerizing only the specific portion by the ultraviolet light irradiation using a mask, and then, performing the polymerization by emitting light to the mask while maintaining the state described above.
The optically anisotropic body obtained by polymerizing the polymerizable liquid crystal composition of the present invention can be used as a single body of the optically anisotropic body by being separated from the substrate or can be used as the optically anisotropic body as it is without being peeled from the substrate. Particularly, it is useful to use the optically anisotropic body as a laminated substrate or use the optically anisotropic body by bonding the optically anisotropic body to another substrate, because the optically anisotropic body hardly contaminates other members.
(Retardation Film)
The retardation film of the present invention is manufactured in the same manner as in a case of the optically anisotropic body of the present invention. In a case where the polymerizable compound represented by General Formula (1) in the polymerizable composition is polymerized in a planar aligned state, a retardation film having birefringence in the plane with respect to the base material is obtained. The retardation film can be used as a homogeneous liquid crystal film. In a case where the polymerizable compound represented by General Formula (1) in the polymerizable composition and the polymerizable chiral compound are polymerized in a planar aligned state, a retardation film having birefringence to the outside of the plane with respect to the base material is obtained. In a case where the polymerizable compound represented by General Formula (1) in the polymerizable composition including the polymerizable discotic compound is polymerized in a planar aligned state, a retardation film having birefringence in the plane and to the outside of the plane with respect to the base material is obtained.
In addition, in a case where the base material includes the retardation film, a retardation film having birefringence obtained by adding the birefringence of the base material and the birefringence of the retardation of the film of the present invention is obtained. In the retardation film, the birefringence of the base material and the birefringence of the retardation of the film may be in the same direction or different directions in the plane of the base material. This is applied in a suitable state for the usage, in accordance with the usage of a liquid crystal device, a display, an optical element, an optical part, a colorant, a security marking, a member for laser emission, an optical film, and a compensation film.
(Phase Difference Patterning Film)
A phase difference patterning film of the present invention is a component obtained by laminating a base material, an alignment film, and a polymer of the polymerizable composition solution, in this order, in the same manner as in a case of the optically anisotropic body of the present invention. In the polymerization step, patterning is performed so as to have partially different phase difference. The patterning may be applied in different directions by linear patterning, lattice patterning, circular patterning, or polygonal patterning. This is applied, in accordance with the usage of a liquid crystal device, a display, an optical element, an optical part, a colorant, a security marking, a member for laser emission, an optical film, and a compensation film.
In a method of obtaining partially different phase difference, an alignment film is provided on a base material, and the alignment treatment is performed so that the polymerizable composition is subjected to patterning alignment, when the polymerizable composition solution of the present invention is applied and dried. As such alignment treatment, fine rubbing treatment, polarized ultraviolet visible light irradiation treatment through a photomask, or fine shape machining treatment is used. As the alignment film, a commonly used well-known oriented film is used. Examples of such an oriented film include compounds such as polyimide, polysiloxane, polyamide, polyvinyl alcohol, polycarbonate, polystyrene, polyphenylene ether, polyarylate, polyethylene terephthalate, polyether sulfone, an epoxy resin, an epoxyacrylate resin, an acrylic resin, a coumarin compound, a chalcone compound, a cinnamate compound, a fulgide compound, an anthraquinone compound, an azo compound, and an arylethene compound. As a compound to be subjected to the alignment treatment by fine rubbing, it is preferable to use a compound in which crystallization of the material is promoted by the alignment treatment or by adding a heating step after the alignment treatment. Among compounds to be subjected to the alignment treatment other than the rubbing, it is preferable to use a photo-alignment material.
EXAMPLES
Hereinafter, the present invention will be described with reference to synthesis examples, examples, and comparative example, but the present invention is not limited thereto. Unless otherwise noted, “part” and “%” are based on mass.
(Preparation of Polymerizable Composition and Manufacturing of Film)
The compound represented by General Formula (I), the compound represented by General Formula (II), Irgacure 907 (manufactured by BASF) as the photopolymerization initiator, methylhydroquinone (MEHQ) as the polymerization inhibitor, liquid paraffin (manufactured by Kanto Kagaku), or R-08 (manufactured by DIC Corporation) as the surfactant, and cyclopentanone (manufactured by Zeon Corporation) or toluene (manufactured by Kanto Kagaku) as the solvent, shown in Tables 1 to 4, were mixed at a ratio shown in the tables, and heated to 80° C. and stirred, and accordingly, uniform polymerizable compositions (coating solutions) used in Example 1 to Example 94 and Comparative Example 1 to Comparative Example 4 were obtained. The coating solution was applied onto a polyimide-attached glass substrate subjected to the rubbing treatment, so that a phase difference at 550 nm becomes 138±5 nm by using a spin coater or an applicator, and dried at 80° C. to 120° C. for 5 minutes. Then, ultraviolet light was irradiated in a nitrogen atmosphere or in the air so that UVA is 600 mJ/cm 2 , and a λ/4 retardation plate having reverse dispersibility was obtained (Example 1 to Example 94). The λ/4 retardation plate and a polarizing plate were bonded to each other so that an angle formed by a slow axis of the retardation plate and an absorption axis of the polarizing plate is 45 degrees, and a wide-band circularly polarizing plate was obtained (Example 1 to Example 94 and Comparative Example 1 to Comparative Example 4).
In addition, in the examples and the comparative examples, compounds used as the compound represented by General Formula (I) and the compound represented by General Formula (II) are the following compounds.
(Evaluation)
(Storage Stability)
Regarding the storage stability, the coating solution obtained as described above was left for 24 hours by observing the coating solution at every 5° C. from 30° C., and the lowest temperature at which crystal was not precipitated was recorded.
(Tilt Angle)
Regarding the tilt angle of the air interface, incident angle dependence of the phase difference of the obtained retardation plate was measured by using a phase difference measurement device RET-100 (manufactured by Otsuka Electronics Co., Ltd.), and the obtained measurement result was analyzed by using computer simulation software LCD-Master (manufactured by Shintech, Inc.).
(Glance)
Regarding glance, GALAXY SII mounted with an organic EL panel manufactured by SAMSUNG was disassembled, a circularly polarizing plate was peeled off and the wide-band circularly polarizing plate described above was bonded thereto, and black coloring observed from the front or an angle of 450 diagonally was evaluated based on the following criteria.
A: Coloring of reflected light is not substantially recognized. (Allowed)
B: Coloring of reflected light is extremely slightly recognized, but there are no practical problems (Allowed)
C: Coloring of reflected light is slightly recognized, but there are no practical problems (Allowed)
D: Coloring of reflected light is recognized and can be allowed according to the purpose (Allowed)
E: Coloring of reflected light is strongly recognized and cannot be allowed.
TABLE 1
Others
Evaluation
General Formula (I)
General Formula (II)
MEHQ
Irgacure
Liquid
Cyclopentanone
Storage
Tilt
Compound
(%)
Compound
(%)
(%)
907 (%)
paraffin (%)
(%)
stability (° C)
(degree)
Glance
Example 1
A11-1
15.2
G1-3
3.7
0.05
1
0.05
80
20
0
B
Example 2
A11-1
15.2
G1-4
3.7
0.05
1
0.05
80
20
1
B
Example 3
A11-1
15.2
G1-5
3.7
0.05
1
0.05
80
20
4
D
Example 4
A11-1
15.2
G3-2
3.7
0.05
1
0.05
80
20
2
A
Example 5
A11-1
15.2
G3-3
3.7
0.05
1
0.05
80
20
3
A
Example 6
A11-2
15.2
G1-2
3.7
0.05
1
0.05
80
20
2
A
Example 7
A11-2
15.2
G1-5
3.7
0.05
1
0.05
80
20
4
D
Example 8
A11-2
15.2
G2-1
3.7
0.05
1
0.05
80
20
0
B
Example 9
A11-2
15.2
G4-1
3.7
0.05
1
0.05
80
20
3
A
Example 10
A12-1
15.2
G1-5
3.7
0.05
1
0.05
80
20
4
C
Example 11
A12-1
15.2
G2-3
3.7
0.05
1
0.05
80
20
0
A
Example 12
A12-1
15.2
G2-4
3.7
0.05
1
0.05
80
20
1
A
Example 13
A12-1
15.2
G4-3
3.7
0.05
1
0.05
80
20
1
A
Example 14
A12-2
15.2
G1-1
3.7
0.05
1
0.05
80
20
1
A
Example 15
A12-2
15.2
G1-3
3.7
0.05
1
0.05
80
20
0
B
Example 16
A12-2
15.2
G2-4
3.7
0.05
1
0.05
80
20
1
A
Example 17
A12-2
15.2
G3-2
3.7
0.05
1
0.05
80
20
3
B
Example 18
A12-2
15.2
G4-3
3.7
0.05
1
0.05
80
20
1
B
Example 19
A12-3
15.2
G1-4
3.7
0.05
1
0.05
80
20
2
B
Example 20
A12-3
15.2
G4-2
3.7
0.05
1
0.05
80
20
3
A
Example 21
A12-4
15.2
G1-3
3.7
0.05
1
0.05
80
15
0
B
Example 22
A12-4
15.2
G1-5
3.7
0.05
1
0.05
80
15
4
D
Example 23
A12-4
15.2
G2-2
3.7
0.05
1
0.05
80
15
0
A
Example 24
A12-4
15.2
G2-5
3.7
0.05
1
0.05
80
15
1
A
Example 25
A12-4
15.2
G4-4
3.7
0.05
1
0.05
80
15
3
B
Example 26
A12-5
15.2
G1-4
3.7
0.05
1
0.05
80
20
2
C
TABLE 2
Others
Evaluation
General Formula (I)
General Formula (II)
MEHQ
Irgacure
Liquid
Cyclopentanone
Storage
Tilt
Compound
(%)
Compound
(%)
(%)
907 (%)
paraffin (%)
(%)
stability (° C)
(degree)
Glance
Example 27
A12-5
15.2
G2-8
3.7
0.05
1
0.05
80
20
3
A
Example 28
A12-5
15.2
G3-1
3.7
0.05
1
0.05
80
20
3
B
Example 29
A12-5
15.2
G3-4
3.7
0.05
1
0.05
80
20
9
D
Example 30
A13-1
15.2
G1-1
3.7
0.05
1
0.05
80
15
1
A
Example 31
A13-1
15.2
G1-3
3.7
0.05
1
0.05
80
15
0
B
Example 32
A13-1
15.2
G2-6
3.7
0.05
1
0.05
80
15
1
A
Example 33
A13-1
15.2
G4-2
3.7
0.05
1
0.05
80
15
3
A
Example 34
A13-1
15.2
G4-3
3.7
0.05
1
0.05
80
15
3
A
Example 35
A13-2
15.2
G1-2
3.7
0.05
1
0.05
80
20
1
A
Example 36
A13-2
15.2
G2-9
3.7
0.05
1
0.05
80
20
0
A
Example 37
A13-2
15.2
G3-3
3.7
0.05
1
0.05
80
20
1
B
Example 38
A13-3
15.2
G1-3
3.7
0.05
1
0.05
80
10
0
B
Example 39
A13-3
15.2
G1-4
3.7
0.05
1
0.05
80
10
2
B
Example 40
A13-3
15.2
G3-1
3.7
0.05
1
0.05
80
10
3
A
Example 41
A13-3
15.2
G4-5
3.7
0.05
1
0.05
80
10
3
A
Example 42
A14-1
15.2
G1-1
3.7
0.05
1
0.05
80
10
1
A
Example 43
A14-1
15.2
G1-3
3.7
0.05
1
0.05
80
10
0
B
Example 44
A14-1
15.2
G1-5
3.7
0.05
1
0.05
80
10
4
D
Example 45
A14-1
15.2
G2-9
3.7
0.05
1
0.05
80
10
0
A
Example 46
A14-1
15.2
G3-3
3.7
0.05
1
0.05
80
10
1
A
Example 47
A14-1
15.2
G4-1
3.7
0.05
1
0.05
80
10
3
A
Example 48
A14-1
15.2
G4-3
3.7
0.05
1
0.05
80
10
1
A
Example 49
A14-2
15.2
G1-3
3.7
0.05
1
0.05
80
15
0
B
Example 50
A14-2
15.2
G2-2
3.7
0.05
1
0.05
80
15
0
A
Example 51
A14-2
15.2
G2-10
3.7
0.05
1
0.05
80
15
0
A
Example 52
A14-2
15.2
G3-2
3.7
0.05
1
0.05
80
15
3
A
TABLE 3
Others
Evaluation
General Formula (I)
General Formula (II)
MEHQ
Irgacure
Liquid
Cyclopentanone
Storage
Tilt
Compound
(%)
Compound
(%)
(%)
907 (%)
paraffin (%)
(%)
stability (° C)
(degree)
Glance
Example 53
A14-2
15.2
G4-5
3.7
0.05
1
0.05
80
15
3
A
Example 54
A14-3
15.2
G1-4
3.7
0.05
1
0.05
80
15
2
B
Example 55
A14-3
15.2
G1-5
3.7
0.05
1
0.05
80
15
4
D
Example 56
A14-3
15.2
G2-8
3.7
0.05
1
0.05
80
15
3
A
Example 57
A14-3
15.2
G3-3
3.7
0.05
1
0.05
80
15
1
A
Example 58
A14-3
15.2
G4-2
3.7
0.05
1
0.05
80
15
3
A
Example 59
A15-1
15.2
G1-2
3.7
0.05
1
0.05
80
20
1
A
Example 60
A15-1
15.2
G1-3
3.7
0.05
1
0.05
80
20
0
B
Example 61
A15-1
15.2
G3-3
3.7
0.05
1
0.05
80
20
1
A
Example 62
A15-2
15.2
G1-1
3.7
0.05
1
0.05
80
20
1
A
Example 63
A15-2
15.2
G3-3
3.7
0.05
1
0.05
80
20
1
A
Example 64
A15-2
15.2
G4-4
3.7
0.05
1
0.05
80
20
3
A
Example 65
A15-3
15.2
G2-1
3.7
0.05
1
0.05
80
20
0
A
Example 66
A15-3
15.2
G3-4
3.7
0.05
1
0.05
80
20
8
D
Example 67
A15-3
15.2
G4-3
3.7
0.05
1
0.05
80
20
0
A
Example 68
A2-1
15.2
G1-1
3.7
0.05
1
0.05
80
25
1
B
Example 69
A2-1
15.2
G3-4
3.7
0.05
1
0.05
80
25
9
D
Example 70
A2-1
15.2
G4-3
3.7
0.05
1
0.05
80
25
1
A
Example 71
A2-2
15.2
G1-3
3.7
0.05
1
0.05
80
25
0
C
Example 72
A2-2
15.2
G4-3
3.7
0.05
1
0.05
80
25
0
A
Example 73
A2-3
15.2
G1-2
3.7
0.05
1
0.05
80
25
1
A
Example 74
A2-4
15.2
G1-2
3.7
0.05
1
0.05
80
25
0
A
Example 75
A2-5
15.2
G1-2
3.7
0.05
1
0.05
80
15
1
A
Example 76
A3-1
15.2
G1-5
3.7
0.05
1
0.05
80
25
4
D
Example 77
A3-1
15.2
G4-3
3.7
0.05
1
0.05
80
25
0
A
Example 78
B11-1
15.2
G1-3
3.7
0.05
1
0.05
80
15
6
C
TABLE 4
Others
Evaluation
General Formula (I)
General Formula (II)
MEHQ
Irgacure
Liquid
Cyclopentanone
Storage
Tilt
Compound
(%)
Compound
(%)
(%)
907 (%)
paraffin (%)
(%)
stability (° C)
(degree)
Glance
Example 79
B11-1
15.2
G1-5
3.7
0.05
1
0.05
80
15
3
C
Example 80
B11-1
15.2
G4-3
3.7
0.05
1
0.05
80
15
1
A
Example 81
B11-2
15.2
G4-3
3.7
0.05
1
0.05
80
10
1
A
Example 82
B11-7
15.2
G1-1
3.7
0.05
1
0.05
80
10
0
A
Example 83
B11-7
15.2
G1-5
3.7
0.05
1
0.05
80
10
3
C
Example 84
B11-8
15.2
G2-4
3.7
0.05
1
0.05
80
15
0
A
Example 85
B3-1
15.2
G4-3
3.7
0.05
1
0.05
80
15
1
A
Example 86
C11-1
15.2
G1-3
3.7
0.05
1
0.05
80
15
2
B
Example 87
C11-2
15.2
G1-3
3.7
0.05
1
0.05
80
15
1
B
Example 88
C11-5
15.2
G1-3
3.7
0.05
1
0.05
80
20
2
B
Example 89
C11-6
15.2
G1-3
3.7
0.05
1
0.05
80
15
2
B
Example 90
C11-9
15.2
G1-3
3.7
0.05
1
0.05
80
20
1
C
Example 91
C12-1
15.2
G4-3
3.7
0.05
1
0.05
80
15
1
A
Example 92
C12-3
15.2
G4-3
3.7
0.05
1
0.05
80
15
1
A
Example 93
C2-1
15.2
G1-3
3.7
0.05
1
0.05
80
20
1
B
Example 94
C3-1
15.2
G1-3
3.7
0.05
1
0.05
80
20
2
B
Comparative
G1-3
9.4
G1-6
9.5
0.05
1
0.05
80
15
2
E
Example 1
Comparative
G1-5
15
G1-6
3.9
0.05
1
0.05
80
15
3
E
Example 2
Comparative
G1-5
15.2
G3-4
3.7
0.05
1
0.05
80
10
13
E
Example 3
Comparative
G2-2
15.2
G2-8
3.7
0.05
1
0.05
80
30
1
E
Example 4
TABLE 5
Others
Evaluation
General Formula (I)
General Formula (II)
MEHQ
Irgacure
Liquid
Cyclopentanone
Storage
Tilt
Glance
Compound
(%)
Compound
(%)
(%)
907 (%)
paraffin (%)
(%)
stability (° C)
(degree)
Front
Example 95
A12-16
15.2
G1-3
3.7
0.05
1
0.05
80
5
0
A
Example 96
A12-17
15.2
G1-3
3.7
0.05
1
0.05
80
5
0
A
Example 97
A12-18
15.2
G1-3
3.7
0.05
1
0.05
80
0
0
A
Example 98
A141-1
15.2
G1-3
3.7
0.05
1
0.05
80
0
2
A
Example 99
A141-2
15.2
G1-3
3.7
0.05
1
0.05
80
0
1
A
Example 100
A141-3
15.2
G1-3
3.7
0.05
1
0.05
80
0
1
A
Example 101
A141-4
15.2
G1-3
3.7
0.05
1
0.05
80
0
1
A
Example 102
A141-5
15.2
G1-3
3.7
0.05
1
0.05
80
0
1
A
Example 103
A141-6
15.2
G1-3
3.7
0.05
1
0.05
80
0
2
A
Example 104
A141-7
15.2
G1-3
3.7
0.05
1
0.05
80
0
2
A
Example 105
A141-8
15.2
G1-3
3.7
0.05
1
0.05
80
0
1
A
Example 106
A141-9
15.2
G1-3
3.7
0.05
1
0.05
80
0
2
A
Example 107
A141-10
15.2
G1-3
3.7
0.05
1
0.05
80
0
1
A
Example 108
A141-11
15.2
G1-3
3.7
0.05
1
0.05
80
0
1
A
Example 109
A141-12
15.2
G1-3
3.7
0.05
1
0.05
80
0
1
A
Example 110
A141-13
15.2
G1-3
3.7
0.05
1
0.05
80
0
1
A
Example 111
A141-14
15.2
G1-3
3.7
0.05
1
0.05
80
0
2
A
Example 112
A141-15
15.2
G1-3
3.7
0.05
1
0.05
80
0
2
A
Example 113
A141-16
15.2
G1-3
3.7
0.05
1
0.05
80
0
2
A
Example 114
A141-17
15.2
G1-3
3.7
0.05
1
0.05
80
0
2
A
TABLE 6
Others
Evaluation
General Formula (I)
General Formula (II)
MEHQ
Irgacure
Liquid
Cyclopentanone
Storage
Tilt
Glance
Compound
(%)
Compound
(%)
(%)
907 (%)
paraffin (%)
(%)
stability (° C)
(degree)
Front
Example 115
A141-18
15.2
G1-3
3.7
0.05
1
0.05
80
0
2
A
Example 116
A141-19
15.2
G1-3
3.7
0.05
1
0.05
80
0
2
A
Example 117
A141-20
15.2
G1-3
3.7
0.05
1
0.05
80
0
2
A
Example 118
A141-21
15.2
G1-3
3.7
0.05
1
0.05
80
0
1
A
Example 119
A141-22
15.2
G1-3
3.7
0.05
1
0.05
80
0
0
A
Example 120
A141-23
15.2
G1-3
3.7
0.05
1
0.05
80
0
0
A
Example 121
A141-24
15.2
G1-3
3.7
0.05
1
0.05
80
0
0
A
Example 122
A141-25
15.2
G1-3
3.7
0.05
1
0.05
80
0
0
A
Example 123
A141-26
15.2
G1-3
3.7
0.05
1
0.05
80
0
0
A
Example 124
A141-27
15.2
G1-3
3.7
0.05
1
0.05
80
0
0
A
Example 125
A141-28
15.2
G1-3
3.7
0.05
1
0.05
80
0
0
A
Example 126
A141-29
15.2
G1-3
3.7
0.05
1
0.05
80
0
0
A
Example 127
A141-30
15.2
G1-3
3.7
0.05
1
0.05
80
0
0
A
Example 128
A141-31
15.2
G1-3
3.7
0.05
1
0.05
80
0
0
A
Example 129
A141-32
15.2
G1-3
3.7
0.05
1
0.05
80
0
0
A
Example 130
A141-33
15.2
G1-3
3.7
0.05
1
0.05
80
0
0
A
Example 131
A142-1
15.2
G1-3
3.7
0.05
1
0.05
80
0
1
A
Example 132
A142-2
15.2
G1-3
3.7
0.05
1
0.05
80
−5
1
A
Example 133
A142-3
15.2
G1-3
3.7
0.05
1
0.05
80
−5
1
A
Example 134
A142-4
15.2
G1-3
3.7
0.05
1
0.05
80
−5
1
A
TABLE 7
Others
Evaluation
General Formula (I)
General Formula (II)
MEHQ
Irgacure
Liquid
Cyclopentanone
Storage
Tilt
Glance
Compound
(%)
Compound
(%)
(%)
907 (%)
paraffin (%)
(%)
stability (° C)
(degree)
Front
Example 135
A142-5
15.2
G1-3
3.7
0.05
1
0.05
80
−5
1
A
Example 136
A142-6
15.2
G1-3
3.7
0.05
1
0.05
80
−5
1
A
Example 137
A142-7
15.2
G1-3
3.7
0.05
1
0.05
80
−5
1
A
Example 138
A142-8
15.2
G1-3
3.7
0.05
1
0.05
80
−5
1
A
Example 139
A142-9
15.2
G1-3
3.7
0.05
1
0.05
80
−5
1
A
Example 140
A142-10
15.2
G1-3
3.7
0.05
1
0.05
80
−5
0
A
Example 141
A142-11
15.2
G1-3
3.7
0.05
1
0.05
80
−5
0
A
Example 142
A142-12
15.2
G1-3
3.7
0.05
1
0.05
80
−5
0
A
Example 143
A142-13
15.2
G1-3
3.7
0.05
1
0.05
80
−5
0
A
Example 144
A142-14
15.2
G1-3
3.7
0.05
1
0.05
80
−5
0
A
Example 145
A142-15
15.2
G1-3
3.7
0.05
1
0.05
80
−5
0
A
Example 146
A143-1
15.2
G1-3
3.7
0.05
1
0.05
80
−5
0
A
Example 147
A143-2
15.2
G1-3
3.7
0.05
1
0.05
80
−5
0
A
Example 148
A144-1
15.2
G1-3
3.7
0.05
1
0.05
80
0
0
A
TABLE 8
Others
Cyclo-
Evaluation
General Formula (I)
General Formula (II)
MEHQ
Irgacure
Liquid
pentanone
Storage
Tilt
Glance
Glance
Compound
(%)
Compound
(%)
(%)
907 (%)
paraffin (%)
(%)
stability (° C)
(degree)
Front
45°
Example 149
A11-1
15.2
G3-5
3.7
0.05
1
0.02
80
30
65
A
B
Example 150
A11-1
15.2
G4-3
3.7
0.05
1
0.02
80
30
60
A
B
Example 151
A11-1
15.2
G1-6
3.7
0.05
1
0.02
80
30
3
B
D
Example 152
A11-1
15.2
G3-4
3.7
0.05
1
0.02
80
30
9
C
D
Example 153
A11-2
15.2
G3-5
3.7
0.05
1
0.02
80
30
60
A
B
Example 154
A11-2
15.2
G3-2
3.7
0.05
1
0.02
80
30
55
A
B
Example 155
A11-2
15.2
G1-2
3.7
0.05
1
0.02
80
30
3
A
C
Example 156
A11-3
15.2
G4-3
3.7
0.05
1
0.02
80
30
65
A
B
Example 157
A11-3
15.2
G1-6
3.7
0.05
1
0.02
80
30
4
B
D
Example 158
A11-3
15.2
G3-4
3.7
0.05
1
0.02
80
30
8
C
D
Example 159
A12-1
15.2
G3-5
3.7
0.05
1
0.02
80
30
60
A
B
Example 160
A12-1
15.2
G4-3
3.7
0.05
1
0.02
80
30
60
A
B
Example 161
A12-1
15.2
G1-6
3.7
0.05
1
0.02
80
30
2
A
C
Example 162
A12-1
15.2
G3-4
3.7
0.05
1
0.02
80
30
9
C
D
Example 163
A12-2
15.2
G3-5
3.7
0.05
1
0.02
80
30
60
A
B
Example 164
A12-2
15.2
G1-2
3.7
0.05
1
0.02
80
30
2
A
C
Example 165
A12-3
15.2
G3-5
3.7
0.05
1
0.02
80
30
65
A
B
Example 166
A12-3
15.2
G4-3
3.7
0.05
1
0.02
80
30
60
A
B
Example 167
A12-3
15.2
G1-6
3.7
0.05
1
0.02
80
30
2
A
C
Example 168
A12-16
15.2
G3-5
3.7
0.05
1
0.02
80
20
60
A
B
TABLE 9
Others
Cyclo-
Evaluation
General Formula (I)
General Formula (II)
MEHQ
Irgacure
Liquid
pentanone
Storage
Tilt
Glance
Glance
Compound
(%)
Compound
(%)
(%)
907 (%)
paraffin (%)
(%)
stability (° C)
(degree)
Front
45°
Example 169
A12-16
15.2
G4-3
3.7
0.05
1
0.02
80
20
55
A
B
Example 170
A12-16
15.2
G1-6
3.7
0.05
1
0.02
80
20
4
A
C
Example 171
A12-16
15.2
G3-4
3.7
0.05
1
0.02
80
20
8
C
D
Example 172
A12-17
15.2
G3-5
3.7
0.05
1
0.02
80
20
65
A
B
Example 173
A12-17
15.2
G3-2
3.7
0.05
1
0.02
80
20
60
A
B
Example 174
A12-17
15.2
G1-2
3.7
0.05
1
0.02
80
20
2
A
C
Example 175
A12-18
15.2
G3-5
3.7
0.05
1
0.02
80
10
65
A
B
Example 176
A12-18
15.2
G4-3
3.7
0.05
1
0.02
80
10
60
A
B
Example 177
A12-18
15.2
G1-6
3.7
0.05
1
0.02
80
10
3
A
C
Example 178
A13-1
15.2
G3-5
3.7
0.05
1
0.02
80
25
60
A
B
Example 179
A13-1
15.2
G1-6
3.7
0.05
1
0.02
80
25
1
A
C
Example 180
A13-1
15.2
G3-4
3.7
0.05
1
0.02
80
25
8
C
D
Example 181
A13-2
15.2
G3-5
3.7
0.05
1
0.02
80
25
60
A
B
Example 182
A13-2
15.2
G4-3
3.7
0.05
1
0.02
80
25
55
A
B
Example 183
A13-2
15.2
G1-2
3.7
0.05
1
0.02
80
25
2
A
C
Example 184
A13-3
15.2
G3-5
3.7
0.05
1
0.02
80
25
60
A
B
Example 185
A13-3
15.2
G1-6
3.7
0.05
1
0.02
80
25
1
B
D
Example 186
A141-22
15.2
G3-5
3.7
0.05
1
0.02
80
10
70
A
A
Example 187
A141-22
15.2
G4-3
3.7
0.05
1
0.02
80
10
65
A
A
Example 188
A141-22
15.2
G1-6
3.7
0.05
1
0.02
80
10
1
A
C
TABLE 10
Others
Cyclo-
Evaluation
General Formula (I)
General Formula (II)
MEHQ
Irgacure
Liquid
pentanone
Storage
Tilt
Glance
Glance
Compound
(%)
Compound
(%)
(%)
907 (%)
paraffin (%)
(%)
stability (° C)
(degree)
Front
45°
Example 189
A141-22
15.2
G3-4
3.7
0.05
1
0.02
80
10
5
C
D
Example 190
A141-23
15.2
G3-5
3.7
0.05
1
0.02
80
10
70
A
A
Example 191
A141-23
15.2
G3-2
3.7
0.05
1
0.02
80
10
65
A
A
Example 192
A141-23
15.2
G1-6
3.7
0.05
1
0.02
80
10
2
A
C
Example 193
A141-24
15.2
G3-5
3.7
0.05
1
0.02
80
10
65
A
A
Example 194
A141-24
15.2
G4-3
3.7
0.05
1
0.02
80
10
65
A
A
Example 195
A141-24
15.2
G1-2
3.7
0.05
1
0.02
80
10
3
A
C
Example 196
A141-24
15.2
G3-4
3.7
0.05
1
0.02
80
10
5
C
D
Example 197
A141-25
15.2
G3-5
3.7
0.05
1
0.02
80
10
65
A
A
Example 198
A141-25
15.2
G3-2
3.7
0.05
1
0.02
80
10
65
A
A
Example 199
A141-25
15.2
G1-6
3.7
0.05
1
0.02
80
10
1
A
C
Example 200
A141-26
15.2
G3-5
3.7
0.05
1
0.02
80
10
65
A
A
Example 201
A141-26
15.2
G4-3
3.7
0.05
1
0.02
80
10
65
A
A
Example 202
A141-26
15.2
G1-6
3.7
0.05
1
0.02
80
10
4
A
C
Example 203
A141-27
15.2
G3-5
3.7
0.05
1
0.02
80
10
65
A
A
Example 204
A141-27
15.2
G3-2
3.7
0.05
1
0.02
80
10
65
A
A
Example 205
A141-27
15.2
G1-2
3.7
0.05
1
0.02
80
10
2
A
C
Example 206
A141-28
15.2
G3-5
3.7
0.05
1
0.02
80
10
65
A
A
Example 207
A141-28
15.2
G4-3
3.7
0.05
1
0.02
80
10
65
A
A
Example 208
A141-28
15.2
G1-6
3.7
0.05
1
0.02
80
10
3
A
C
TABLE 11
Others
Cyclo-
Evaluation
General Formula (I)
General Formula (II)
MEHQ
Irgacure
Liquid
pentanone
Storage
Tilt
Glance
Glance
Compound
(%)
Compound
(%)
(%)
907 (%)
paraffin (%)
(%)
stability (° C)
(degree)
Front
45°
Example 209
A141-29
15.2
G3-5
3.7
0.05
1
0.02
80
10
70
A
A
Example 210
A141-29
15.2
G4-3
3.7
0.05
1
0.02
80
10
70
A
A
Example 211
A141-29
15.2
G1-6
3.7
0.05
1
0.02
80
10
1
A
C
Example 212
A141-30
15.2
G3-5
3.7
0.05
1
0.02
80
10
70
A
A
Example 213
A141-30
15.2
G3-2
3.7
0.05
1
0.02
80
10
65
A
A
Example 214
A141-30
15.2
G1-2
3.7
0.05
1
0.02
80
10
2
A
C
Example 215
A141-31
15.2
G3-5
3.7
0.05
1
0.02
80
10
70
A
A
Example 216
A141-31
15.2
G4-3
3.7
0.05
1
0.02
80
10
65
A
A
Example 217
A141-31
15.2
G1-6
3.7
0.05
1
0.02
80
10
1
A
C
Example 218
A141-32
15.2
G3-5
3.7
0.05
1
0.02
80
10
70
A
A
Example 219
A141-32
15.2
G4-3
3.7
0.05
1
0.02
80
10
70
A
A
Example 220
A141-32
15.2
G1-2
3.7
0.05
1
0.02
80
10
2
A
C
Example 221
A141-33
15.2
G3-5
3.7
0.05
1
0.02
80
10
70
A
A
Example 222
A141-33
15.2
G3-2
3.7
0.05
1
0.02
80
10
65
A
A
Example 223
A141-33
15.2
G1-6
3.7
0.05
1
0.02
80
10
1
A
C
Example 224
A141-33
15.2
G3-4
3.7
0.05
1
0.02
80
10
4
C
D
Example 225
A142-10
15.2
G3-5
3.7
0.05
1
0.02
80
5
70
A
A
Example 226
A142-10
15.2
G3-2
3.7
0.05
1
0.02
80
5
65
A
A
Example 227
A142-10
15.2
G1-2
3.7
0.05
1
0.02
80
5
3
A
C
Example 228
A142-10
15.2
G3-4
3.7
0.05
1
0.02
80
5
6
C
D
TABLE 12
Others
Cyclo-
Evaluation
General Formula (I)
General Formula (II)
MEHQ
Irgacure
Liquid
pentanone
Storage
Tilt
Glance
Glance
Compound
(%)
Compound
(%)
(%)
907 (%)
paraffin (%)
(%)
stability (° C)
(degree)
Front
45°
Example 229
A142-11
15.2
G3-5
3.7
0.05
1
0.02
80
5
70
A
A
Example 230
A142-11
15.2
G4-3
3.7
0.05
1
0.02
80
5
65
A
A
Example 231
A142-11
15.2
G1-6
3.7
0.05
1
0.02
80
5
1
A
C
Example 232
A142-12
15.2
G3-5
3.7
0.05
1
0.02
80
5
65
A
A
Example 233
A142-12
15.2
G4-3
3.7
0.05
1
0.02
80
5
65
A
A
Example 234
A142-12
15.2
G1-2
3.7
0.05
1
0.02
80
5
1
A
C
Example 235
A142-13
15.2
G3-5
3.7
0.05
1
0.02
80
5
70
A
A
Example 236
A142-13
15.2
G3-2
3.7
0.05
1
0.02
80
5
65
A
A
Example 237
A142-13
15.2
G1-6
3.7
0.05
1
0.02
80
5
2
A
C
Example 238
A142-13
15.2
G3-4
3.7
0.05
1
0.02
80
5
6
C
D
Example 239
A142-14
15.2
G3-5
3.7
0.05
1
0.02
80
0
70
A
A
Example 240
A142-14
15.2
G4-3
3.7
0.05
1
0.02
80
0
70
A
A
Example 241
A142-14
15.2
G1-6
3.7
0.05
1
0.02
80
0
2
A
C
Example 242
A142-14
15.2
G3-4
3.7
0.05
1
0.02
80
0
5
C
D
Example 243
A142-15
15.2
G3-5
3.7
0.05
1
0.02
80
0
70
A
A
Example 244
A142-15
15.2
G3-2
3.7
0.05
1
0.02
80
0
65
A
A
Example 245
A142-15
15.2
G1-2
3.7
0.05
1
0.02
80
0
1
A
C
Example 246
A143-1
15.2
G3-5
3.7
0.05
1
0.02
80
0
70
A
A
Example 247
A143-1
15.2
G4-3
3.7
0.05
1
0.02
80
0
70
A
A
Example 248
A143-1
15.2
G1-6
3.7
0.05
1
0.02
80
0
2
A
C
TABLE 13
Others
Cyclo-
Evaluation
General Formula (I)
General Formula (II)
MEHQ
Irgacure
Liquid
pentanone
Storage
Tilt
Glance
Glance
Compound
(%)
Compound
(%)
(%)
907 (%)
paraffin (%)
(%)
stability (° C)
(degree)
Front
45°
Example 249
A143-1
15.2
G3-4
3.7
0.05
1
0.02
80
0
5
C
D
Example 250
A143-2
15.2
G3-5
3.7
0.05
1
0.02
80
0
70
A
A
Example 251
A143-2
15.2
G3-2
3.7
0.05
1
0.02
80
0
65
A
A
Example 252
A143-2
15.2
G1-2
3.7
0.05
1
0.02
80
0
1
A
C
Example 253
A143-2
15.2
G3-4
3.7
0.05
1
0.02
80
0
5
C
D
Comparative
G1-3
9.4
G2-1
9.5
0.05
1
0.02
80
25
2
E
E
Example 5
Comparative
G1-5
15
G2-1
3.9
0.05
1
0.02
80
20
2
E
E
Example 6
Comparative
G1-6
15.2
G3-5
3.7
0.05
1
0.02
80
0
70
E
E
Example 7
Comparative
G2-3
15.2
G4-3
3.7
0.05
1
0.02
80
15
60
E
E
Example 8
From the results described above, it is found that the compositions of the examples have excellent glance, compared to the compositions of the comparative examples.
You are contracting for Polymerizable composition and optically anisotropic body
Expert Polymerizable composition and optically anisotropic body
You are commenting for Polymerizable composition and optically anisotropic body