WO2022059470A1

WO2022059470A1 - Liquid crystal composition, compound, optically anisotropic film, optical film, polarizing plate, and image display device

Info

Publication number: WO2022059470A1
Application number: PCT/JP2021/031726
Authority: WO
Inventors: 有次吉田; 徹渡辺; 愛子吉田; 淳石山
Original assignee: 富士フイルム株式会社
Priority date: 2020-09-18
Filing date: 2021-08-30
Publication date: 2022-03-24
Also published as: CN116249757A; JPWO2022059470A1; KR20230051243A

Abstract

The present invention addresses the problem of providing: a liquid crystal composition capable of suppressing the occurrence of orientation defects in an optically anisotropic film; a compound; an optically anisotropic film; an optical film; a polarizing plate; and an image display device. A liquid crystal composition according to the present invention contains a liquid crystal compound, and a compound represented by formula (II).

Description

Liquid crystal composition, compound, optically anisotropic film, optical film, polarizing plate and image display device

The present invention relates to a liquid crystal composition, a compound, an optically anisotropic film, an optical film, a polarizing plate, and an image display device.

The polymerizable liquid crystal compound exhibiting reverse wavelength dispersibility is a thin film of a retardation film (optically anisotropic film) because it enables accurate conversion of light wavelength over a wide wavelength range and has a high refractive index. Since it has characteristics such as being able to be transformed, it is being actively researched.
Further, as a polymerizable liquid crystal compound exhibiting reverse wavelength dispersibility, a T-type molecular design guideline is generally taken, the wavelength of the major axis of the molecule is shortened, and the wavelength of the minor axis located at the center of the molecule is the long wavelength. Is required to be.

For example, Patent Document 1 describes a polymerizable liquid crystal compound represented by the following formula (1) ([Claim 1]).

International Publication No. 2019/017445

The present inventors have studied the polymerizable liquid crystal compound described in Patent Document 1, and found that an optically anisotropic film is formed depending on other components of the polymerizable liquid crystal composition containing the polymerizable liquid crystal compound. It was clarified that an orientation defect may occur in the liquid crystal display.

Therefore, it is an object of the present invention to provide a liquid crystal composition, a compound, an optically anisotropic film, an optical film, a polarizing plate, and an image display device capable of suppressing the occurrence of orientation defects in the optically anisotropic film. do.

As a result of diligent studies to achieve the above problems, the present inventors have formed an optically anisotropic film by using a liquid crystal composition containing a liquid crystal compound and a compound represented by the formula (II) described later. The present invention has been completed by finding that it is possible to suppress the orientation defect of the liquid crystal display.
That is, it was found that the above problem can be achieved by the following configuration.

[1] A liquid crystal composition containing a liquid crystal compound and a compound represented by the formula (II) described later.
[2] The liquid crystal composition according to [1], wherein at least one M in the formula (II) described later represents an aromatic ring having a maximum absorption wavelength of 280 to 420 nm.
[3] At least one M in the formula (II) described later represents any aromatic ring selected from the group consisting of the groups represented by the formulas (M-1) to (M-7) described later. , [1] or [2].
[4] The liquid crystal composition according to any one of [1] to [3], wherein T in the formula (II) described later represents a polymerizable group.
[5] T in the formula (II) described later represents any polymerizable group selected from the group consisting of the groups represented by the formulas (P-1) to (P-20) described later. 1] The liquid crystal composition according to any one of [4].
[6] The liquid crystal composition according to any one of [1] to [5], wherein the liquid crystal compound has a reverse wavelength dispersibility.
[7] The liquid crystal compound is a compound having any aromatic ring selected from the group consisting of groups represented by the formulas (Ar-1) to (Ar-7) described later, [1] to [6]. ] The liquid crystal composition according to any one of.
[8] The liquid crystal composition according to any one of [1] to [7], wherein the liquid crystal compound has a polymerizable group.
[9] The liquid crystal display according to [8], wherein the polymerizable group represents any polymerizable group selected from the group consisting of groups represented by the formulas (P-1) to (P-20) described later. Composition.

[10] A compound represented by the formula (II) described later.
[11] The compound according to [10], wherein at least one M in the formula (II) described later represents an aromatic ring having a maximum absorption wavelength of 280 to 420 nm.
[12] At least one M in the formula (II) described later represents any aromatic ring selected from the group consisting of the groups represented by the formulas (M-1) to (M-7) described later. , [10] or [11].
[13] The compound according to any one of [10] to [12], wherein T in the formula (II) described later represents a polymerizable group.
[14] T in the formula (II) described later represents any polymerizable group selected from the group consisting of the groups represented by the formulas (P-1) to (P-20) described later. 10] The compound according to any one of [13].

[15] An optically anisotropic film obtained by polymerizing the liquid crystal composition according to any one of [1] to [9].
[16] The optically anisotropic film according to [15], which satisfies the formula (III) described later.
[17] An optical film having the optically anisotropic film according to [15] or [16].
[18] A polarizing plate having the optical film according to [17] and a polarizing element.
[19] An image display device having the optical film according to [17] or the polarizing plate according to [18].

According to the present invention, it is possible to provide a liquid crystal composition, a compound, an optically anisotropic film, an optical film, a polarizing plate, and an image display device capable of suppressing the occurrence of orientation defects in the optically anisotropic film.

FIG. 1A is a schematic cross-sectional view showing an example of the optical film of the present invention. FIG. 1B is a schematic cross-sectional view showing an example of the optical film of the present invention. FIG. 1C is a schematic cross-sectional view showing an example of the optical film of the present invention.

Hereinafter, the present invention will be described in detail.
The description of the constituent elements described below may be based on the representative embodiments of the present invention, but the present invention is not limited to such embodiments.
In the present specification, the numerical range represented by using "-" means a range including the numerical values before and after "-" as the lower limit value and the upper limit value.
Further, in the present specification, as each component, a substance corresponding to each component may be used alone or in combination of two or more. Here, when two or more kinds of substances are used in combination for each component, the content of the component means the total content of the substances used in combination unless otherwise specified.
Further, in the present specification, the bonding direction of the divalent group (for example, -CO-NR-) described is not particularly limited unless the bonding position is specified, and for example, the formula described later (for example) When D ¹ in I) is -CO-NR-, if the position bonded to the G ¹ side is * 1 and the position bonded to the Ar ¹ side is * 2, D ¹ is * 1. -CO-NR- * 2 may be used, or * 1-NR-CO- * 2 may be used.

[Polymerizable liquid crystal composition]
The liquid crystal composition of the present invention is a liquid crystal composition containing a liquid crystal compound and a compound represented by the formula (II) described later (hereinafter, also abbreviated as "specific compound").

In the present invention, as described above, by using a liquid crystal composition containing a specific compound together with the liquid crystal compound, it is possible to suppress the orientation defect of the formed optically anisotropic film.
This is not clear in detail, but the present inventors speculate as follows.
That is, the presence of the amino group contained in the specific compound breaks the bond (ester bond, etc.) contained in the liquid crystal compound, and the crystallinity of the liquid crystal compound is lowered. It is probable that it could be suppressed. It is also considered that the occurrence of orientation defects due to the crystallization of the liquid crystal compound could be suppressed by lowering the phase transition temperature of the liquid crystal composition by blending the specific compound.
Hereinafter, each component of the liquid crystal composition of the present invention will be described in detail.

[Specific compound]
The specific compound contained in the liquid crystal composition of the present invention is a compound represented by the following formula (II).

In the above formula (II), R ²¹ and R ²² each independently represent a hydrogen atom or an alkyl group.
Further, in the above formula (II), R ²³ represents a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group.
Further, in the above formula (II), SP ²¹ and SP ²² each independently represent a single bond or an alkylene group. However, the hydrogen atom contained in the alkylene group is 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 carbon number of 1 to 20. It may be substituted with an alkyl group. Further, among the -CH _2- constituting the alkylene group, one or two or more -CH ₂ -that are not adjacent to each other are -O-, -S-, -CO-, -COO-, -OCO-. , -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -CO-NR ^24- , -NH-CO-, -NR ²⁵ -CO-, -NH- , -NR ²⁶ -or may be substituted with -C≡C-, where R ²⁴ -R ²⁶ represent a substituent.
Further, in the above formula (II), D ²¹ and D ²² are independently single-bonded or -CO-, -O-, -S-, -C (= S)-, -CR ²⁷ R ²⁸ . -, -CR ²⁹ = CR ^30- , -NH-, -NR ^31- , or a divalent linking group consisting of a combination of two or more thereof, and R ²⁷ to R ³¹ represent a substituent.
Further, in the above formula (II), M represents an aromatic ring, an alicyclic ring, or a heterocycle which may have a substituent.
Further, in the above equation (II), m represents an integer of 3 or more, and the plurality of Ms may be the same or different, and the plurality of D ^22s may be the same or different. You may.
Further, in the above formula (II), T represents a hydrogen atom, an alkyl group, or a polymerizable group.

Here, the substituents indicated by R ²⁴ to R ³¹ (hereinafter, also abbreviated as “substituent X”) include, for example, an alkyl group, an alkoxy group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkylcarbonyloxy group, and an alkylamino. Examples thereof include a group, a dialkylamino group, an alkylamide group, an alkenyl group, an alkynyl group, a halogen atom, a cyano group, a nitro group, an alkylthiol group, and an N-alkylcarbamate group, among which an alkyl group, an alkoxy group and an alkoxy group are used. A carbonyl group, an alkylcarbonyloxy group, or a halogen atom is preferred.
The alkyl group is preferably a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, and an alkyl group having 1 to 8 carbon atoms (for example, methyl group, ethyl group, propyl group, isopropyl group, n). -Butyl group, isobutyl group, sec-butyl group, t-butyl group, cyclohexyl group, etc.) are more preferable, an alkyl group having 1 to 4 carbon atoms is further preferable, and a methyl group or an ethyl group is particularly preferable.
As the alkoxy group, an alkoxy group having 1 to 18 carbon atoms is preferable, an alkoxy group having 1 to 8 carbon atoms (for example, a methoxy group, an ethoxy group, an n-butoxy group, a methoxyethoxy group, etc.) is more preferable, and an alkoxy group having 1 carbon atom is preferable. Alkoxy groups of -4 are more preferred, and methoxy or ethoxy groups are particularly preferred.
Examples of the alkoxycarbonyl group include a group in which an oxycarbonyl group (—O—CO— group) is bonded to the alkyl group exemplified above, and among them, a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group or an isopropoxy. A carbonyl group is preferred, a methoxycarbonyl group is more preferred.
Examples of the alkylcarbonyloxy group include a group in which a carbonyloxy group (-CO-O- group) is bonded to the alkyl group exemplified above, and among them, a methylcarbonyloxy group, an ethylcarbonyloxy group, and an n-propylcarbonyloxy group. A group or an isopropylcarbonyloxy group is preferable, and a methylcarbonyloxy group is more preferable.
Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and among them, a fluorine atom or a chlorine atom is preferable.

In the above formula (II), examples of the alkyl group represented by one aspect of R ²¹ and R ²² include the same alkyl groups as those exemplified for the above-mentioned substituent X.
Further, as R ²¹ and R ²² , it is preferable to represent a methyl group.

In the above formula (II), R ²³ represents a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group as described above, but preferably represents a hydrogen atom.

In the above formula (II), examples of the alkylene group represented by one aspect of SP ²¹ and SP ²² include a linear or branched alkylene group having 1 to 12 carbon atoms, and specifically, a methylene group. , Ethylene group, propylene group, butylene group, pentylene group, hexylene group, methylhexylene group, heptylene group and the like.
Here, as described above, in the alkylene group shown in one aspect of SP ²¹ and SP ²² , the hydrogen atom contained in the alkylene group is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, or a cyano. It may be substituted with a group, a nitro group, an isocyano group, a thioisocyano group, or an alkyl group having 1 to 20 carbon atoms.
Further, as described above, the alkylene group shown in one aspect of SP ²¹ and SP ²² includes one or two or more non-adjacent-CH _2- among the -CH _2- constituting the alkylene group. O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -CO-NR ²⁴ -, -NH-CO-, -NR ²⁵ -CO-, -NH-, -NR ^26- , or -C≡C- may be substituted.
Further, the SP ²¹ and SP ²² are one or adjacent to a linear alkylene group having ₂ to 10 carbon atoms or a linear alkylene group having 2 to 12 carbon atoms. It is preferable to represent a divalent linking group in which two or more -CH _2- are substituted with -O-, -COO- or -OCO-, and a linear alkylene group having 2 to 8 carbon atoms is preferable. Or, one of -CH _2- constituting a linear alkylene group having 2 to 8 carbon atoms or two or more non-adjacent-CH ₂ -are substituted with -O-. It is more preferable to represent a linking group.

In the above formula (II), examples of the divalent linking group represented by one aspect of D ²¹ and D ²² include -CO-, -O-, -CO-O-, -C (= S) O-, and so on. -CR ¹ R ^2- , -CR ^{1 R 2--CR 1 R 2-, -O-CR 1} ^R ^2- ^, ^-CR ¹ ^R ² --O-CR ¹ R ^2- , -CO-O-CR ¹ R ^2- , -O-CO-CR ¹ R ^2- , -CR ¹ R ² -O-CO-CR ¹ R ^2- , -CR ¹ R ² -CO-O-CR ¹ R ^2- , -NR ^5- CR ¹ R ^2- , -CO-NR ^5- , and the like can be mentioned. R ¹ , R ² and R ⁵ independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms.
Further, as D ²¹ and D ²² , it is preferable to represent a single bond, -CO-, -O-, or -CO-O-.

In the above formula (II), examples of the aromatic ring represented by one aspect of M include an aromatic ring having 6 to 20 carbon atoms, and specifically, a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthroline ring. Aromatic hydrocarbon rings such as: Fran ring, pyrrole ring, thiophene ring, pyridine ring, thiazole ring, benzothiazole ring and other aromatic heterocycles; represented by the formulas (M-1) to (M-8) described later. Benzene;
In addition, examples of the alicyclic ring shown by one aspect of M include a cycloalkane ring, and specific examples thereof include a cyclohexane ring, a cyclopeptane ring, a cyclooctane ring, a cyclododecane ring, and a cyclododecane ring.
In addition, examples of the heterocycle indicated by one aspect of M include heterocycles other than the above-mentioned aromatic heterocycle, and specifically, for example, a tetrahydrofuran ring, a tetrahydropyran ring, a pyrrolidine ring, a piperidine ring, and a tetrahydrothiophene ring. And so on.
Examples of the substituent that M may have include the same as the above-mentioned substituent X.

In the present invention, at least one M in the above formula (II) represents an aromatic ring having a maximum absorption wavelength at 280 to 420 nm for the reason that the optical anisotropic film formed has better light resistance. Is preferable. In particular, when the number of Ms is an odd number (for example, 3 or 5), it is preferable that the M located at the center represents an aromatic ring having a maximum absorption wavelength at 280 to 420 nm.

Further, in the present invention, at least one M in the above formula (II) is represented by the following formulas (M-1) to (M-7) for the reason that the compatibility with the liquid crystal compound is good. It preferably represents any aromatic ring selected from the group consisting of groups. In particular, when there are an odd number of Ms (for example, 3 or 5), the M located at the center is a group consisting of groups represented by the following formulas (M-1) to (M-7). It is preferable to represent any aromatic ring selected from.

In the above formulas (M-1) to (M-7), * represents a bonding position with D ²¹ or D ²² .

Further, in the above formula (M-1), Q ¹ represents N or CH, Q ² represents -S-, -O-, or -N (R ⁶ )-, and R ⁶ is hydrogen. Represents an atom or an alkyl group having ¹ to 6 carbon atoms, where Y1 is an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent and 3 to 12 carbon atoms which may have a substituent. Represents an aromatic heterocyclic group or an alicyclic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, and one or more of -CH _2- constituting the alicyclic hydrocarbon group is present. It may be substituted with —O—, —S— or —NH—.

Here, the alkyl group having 1 to 6 carbon atoms indicated by R ⁶ is specifically, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and the like. Examples thereof include a tert-butyl group, an n-pentyl group, and an n-hexyl group.

Examples of the aromatic hydrocarbon group having 6 to 12 carbon atoms indicated by Y ¹ include an aryl group such as a phenyl group, a 2,6-diethylphenyl group and a naphthyl group.
Examples of the aromatic heterocyclic group having 3 to 12 carbon atoms indicated by Y ¹ include heteroaryl groups such as a thienyl group, a thiazolyl group, a frill group and a pyridyl group.
Examples of the alicyclic hydrocarbon group having 6 to 20 carbon atoms indicated by Y ¹ include a cyclohexylene group, a cyclopentylene group, a norbornene group, and an adamantylene group.
Examples of the substituent that Y ¹ may have include the same as the above-mentioned substituent X.

Further, in the above formulas (M-1) to (M-7), Z ¹ , Z ² and Z ³ are independently hydrogen atoms, monovalent aliphatic hydrocarbon groups having 1 to 20 carbon atoms, and carbon. A monovalent alicyclic hydrocarbon group having a number of 3 to 20, a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, a monovalent aromatic heterocyclic group having 6 to 20 carbon atoms, a halogen atom, and a cyano group. , Nitro group, -OR ⁷ , -NR ⁸ R ⁹ , -SR ¹⁰ , -COOR ¹¹ or -COR ¹² , where R ⁷ to R ¹² are independently hydrogen atoms or 1 to 6 carbon atoms, respectively. Representing an alkyl group, Z ¹ and Z ² may be bonded to each other to form an aromatic ring.

Here, as the monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, an alkyl group having 1 to 15 carbon atoms is preferable, an alkyl group having 1 to 8 carbon atoms is more preferable, and specifically, a methyl group. , Ethyl group, isopropyl group, tert-pentyl group (1,1-dimethylpropyl group), tert-butyl group, 1,1-dimethyl-3,3-dimethyl-butyl group are more preferable, and methyl group, ethyl group, A tert-butyl group is particularly preferred.
Examples of the monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclodecyl group, a methylcyclohexyl group and an ethylcyclohexyl. Monocyclic saturated hydrocarbon groups such as groups; cyclobutenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, cyclooctenyl group, cyclodecenyl group, cyclopentadienyl group, cyclohexadienyl group, cyclooctadienyl group, cyclodeca Monocyclic unsaturated hydrocarbon groups such as diene; bicyclo [2.2.1] heptyl group, bicyclo [2.2.2] octyl group, tricyclo [5.2.2.10 ^2,6 ] decyl group, Tricyclo [3.3.1.1 ^3,7 ] decyl group, tetracyclo [6.2.1.1 ^3,6 . 0 ^2,7 ] Polycyclic saturated hydrocarbon groups such as dodecyl group and adamantyl group; and the like.
Specific examples of the monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms include a phenyl group, a 2,6-diethylphenyl group, a naphthyl group, a biphenyl group and the like, and have 6 to 12 carbon atoms. Aryl groups (particularly phenyl groups) are preferred.
Specific examples of the monovalent aromatic heterocyclic group having 6 to 20 carbon atoms include a 4-pyridyl group, a 2-furyl group, a 2-thienyl group, a 2-pyrimidinyl group, and a 2-benzothiazolyl group. Can be mentioned.
Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like, and among them, a fluorine atom, a chlorine atom and a bromine atom are preferable.
On the other hand, as the alkyl group having 1 to 6 carbon atoms indicated by R ⁷ to R ¹⁰ , specifically, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group and a sec-butyl group. Groups, tert-butyl group, n-pentyl group, n-hexyl group and the like can be mentioned.

Further, Z ¹ and Z ² may be bonded to each other to form an aromatic ring as described above. For example, Z ¹ and Z ² in the above formula (M-1) may be bonded to each other to form an aromatic ring. Examples of the formed structure include a group represented by the following formula (M-1a). In the following formula (M-1a), * represents a bonding position, and Q ¹ , Q ² and Y ¹ are the same as those described in the above formula (M-1).

Further, in the above formulas (M-2) and (M-3), A ³ and A ⁴ are independently derived from -O-, -N (R ¹³ )-, -S-, and -CO-, respectively. Represents a group selected from the group, where R ¹³ represents a hydrogen atom or a substituent.
Examples of the substituent indicated by R ¹³ include the same as the above-mentioned substituent X.

Further, in the above formula (M-2), X represents a non-metal atom of Group 14 to 16 to which a hydrogen atom or a substituent may be bonded.
Further, as the non-metal atom of Group 14 to 16 indicated by X, for example, an oxygen atom, a sulfur atom, a hydrogen atom or a nitrogen atom to which a substituent is bonded [= ^N -RN1 and ^RN1 are hydrogen atoms or substituents. Represents. ], A carbon atom to which a hydrogen atom or a substituent is bonded [= C- ( ^RC1 ) ₂ , ^RC1 represents a hydrogen atom or a substituent. ] Can be mentioned.
Specific examples of the substituent include an alkyl group, an alkoxy group, an alkyl substituted alkoxy group, a cyclic alkyl group, an aryl group (for example, a phenyl group, a naphthyl group, etc.), a cyano group, an amino group, a nitro group, and an alkyl group. Examples thereof include a carbonyl group, a sulfo group and a hydroxyl group.

Further, in the above formula (M-3), D ⁷ and D ⁸ are independently single-bonded or -CO-, -O-, -S-, -C (= S)-, -CR ¹ respectively. R ^2- , -CR ³ = CR ^4- , -NR ^5- , or a divalent linking group consisting of a combination of two or more of these, and R ¹ to R ⁵ are independent hydrogen atoms, respectively. It represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms.

Here, examples of the divalent linking group shown in one aspect of D ⁷ and D ⁸ include -CO-, -O-, -CO-O-, -C (= S) O-, and -CR ¹ R. ^2- , -CR 1 R ² -CR ¹ R ^2- , -O-CR ¹ R ^2- , -CR ¹ R ² -O-CR ¹ R ^2- , ^{-CO-O-CR 1} ^R ² -,- O-CO-CR ¹ R ^2- , -CR ¹ R ² -O-CO-CR ¹ R ^2- , -CR ¹ R ² -CO-O-CR ¹ R ^2- , -NR ⁵ -CR ¹ R ² -, -CO-NR ^5- , and the like can be mentioned. R ¹ , R ² and R ⁵ independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms.
Of these, any of -CO-, -O-, and -CO-O- is preferable.

Further, in the above formula (M-3), SP ³ and SP ⁴ are independently single-bonded, a linear or branched alkylene group having 1 to 12 carbon atoms, or a direct group having 1 to 12 carbon atoms. One or more of -CH _2- constituting a chain or branched alkylene group is substituted with -O-, -S-, -NH-, -N (Q)-, or -CO-. Represents a linking group of, and Q represents a substituent. Examples of the substituent include the same as the above-mentioned substituent X.

Here, examples of the linear or branched alkylene group having 1 to 12 carbon atoms shown in one aspect of SP ³ and SP ⁴ include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group and a hexylene group. , Methylhexylene group, heptylene group and the like are preferable. As described above, in SP ¹ and SP ² , one or more of -CH _2- constituting a linear or branched alkylene group having 1 to 12 carbon atoms are -O-, -S-, and -NH. It may be a divalent linking group substituted with −, −N (Q) − or −CO—, and the substituent represented by Q is, for example, the same as the above-mentioned substituent X. Can be mentioned.

Further, in the above formula (M-3), L ³ and L ⁴ each independently represent a monovalent organic group.
Examples of the monovalent organic group include an alkyl group, an aryl group, and a heteroaryl group.
The alkyl group may be linear, branched or cyclic, but linear is preferred. The number of carbon atoms of the alkyl group is preferably 1 to 30, more preferably 1 to 20, and even more preferably 1 to 10.
The aryl group may be monocyclic or polycyclic, but monocyclic is preferable. The aryl group preferably has 6 to 25 carbon atoms, more preferably 6 to 10 carbon atoms.
Further, the heteroaryl group may be monocyclic or polycyclic. The number of heteroatoms constituting the heteroaryl group is preferably 1 to 3. As the hetero atom constituting the heteroaryl group, a nitrogen atom, a sulfur atom and an oxygen atom are preferable. The heteroaryl group preferably has 6 to 18 carbon atoms, more preferably 6 to 12 carbon atoms.
Further, the alkyl group, the aryl group and the heteroaryl group may be unsubstituted or may have a substituent. Examples of the substituent include the same as the above-mentioned substituent X.

Further, in the above formulas (M-4) to (M-7), Ax has at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocycle, and has 2 to 30 carbon atoms. Represents an organic group.
Further, in the above formulas (M-4) to (M-7), Ay is a hydrogen atom, an alkyl group having 1 to 12 carbon atoms which may have a substituent, or an aromatic hydrocarbon ring and an aromatic. Represents an organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of group heterocycles.
Here, the aromatic ring in Ax and Ay may have a substituent, or Ax and Ay may be bonded to form a ring.
Further, ^Q3 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent.
Examples of Ax and Ay include those described in paragraphs [0039] to [0995] of International Publication No. 2014/010325.
Specific examples of the alkyl group having 1 to 20 carbon atoms indicated by ^Q3 include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert. -Butyl group, n-pentyl group, n-hexyl group and the like can be mentioned, and examples of the substituent include the same as the above-mentioned substituent X.

Further, in the present invention, at least one M in the above formula (II) represents a cyclohexane ring for the reason that the orientation of the liquid crystal is improved and the moisture resistance of the formed optically anisotropic film is also improved. , It is more preferable to represent a 1,4-cyclohexylene group, and it is even more preferable to represent a trans-1,4-cyclohexylene group. In particular, when the number of M's is odd (for example, 3 or 5), it is preferable that M located outside the center represents a cyclohexane ring.

In the above formula (II), m represents an integer of 3 or more, preferably represents an integer of 3 to 6, and more preferably represents an odd number among the integers of 3 to 6.
The plurality of Ms may be the same or different from each other, and the plurality of D ^22s may be the same or different from each other.

Hereinafter, a specific example of the partial structure represented by-(MD ²² ) _m -in the above formula (II) will be shown. In the specific examples shown below, * represents a bond position, the benzene ring and the cyclohexane ring may be substituted with a condensed ring or a substituent, and some carbon atoms may be replaced with heteroatoms. ..

In the above formula (II), examples of the alkyl group represented by one aspect of T include the same alkyl groups as those exemplified for the above-mentioned substituent X.

In the present invention, it is preferable that T in the above formula (II) represents a polymerizable group for the reason that the strength of the formed optically anisotropic film is improved.
As the polymerizable group, a polymerizable group capable of radical polymerization or cationic polymerization is preferable.
As the radically polymerizable group, a known radically polymerizable group can be used, and suitable examples thereof include an acryloyloxy group and a methacryloyloxy group. In this case, it is known that the acryloyloxy group is generally faster in terms of the polymerization rate, and the acryloyloxy group is preferable from the viewpoint of improving productivity, but the methacryloyloxy group can also be used as the polymerizable group in the same manner.
As the cationically polymerizable group, a known cationically polymerizable group can be used, and specifically, an alicyclic ether group, a cyclic acetal group, a cyclic lactone group, a cyclic thioether group, a spiroorthoester group, and vinyloxy. The group can be mentioned. Of these, an alicyclic ether group or a vinyloxy group is preferable, and an epoxy group, an oxetanyl group, or a vinyloxy group is particularly preferable.
Examples of particularly preferable polymerizable groups include any polymerizable group selected from the group consisting of the groups represented by the following formulas (P-1) to (P-20). Of these, acryloyloxy group or methacryloyloxy group is more preferable. In the following equations (P-1) to (P-20), * represents the bonding position with SP ²² .

Hereinafter, a specific example of the partial structure represented by -SP ²¹ -D ^21- in the above formula (II) will be shown. In the specific examples shown below, * represents a bond position with M, and ** represents a bond position with an oxygen atom.

Hereinafter, a specific example of the partial structure represented by -D ²² -SP ^22- in the above formula (II) will be shown. In the specific examples shown below, * represents a bond position with M, and ** represents a bond position with T.

Specific examples of the specific compound include compounds represented by the following formulas (2-1-1) to (2-1-12) and (2-1) to (2-5).

In the present invention, from the viewpoint of preventing the orientation of the liquid crystal compound from being hindered, the content of the specific compound is preferably 0.05 to 20% by mass with respect to the total mass of the liquid crystal compound and the specific compound described later. It is more preferably 1 to 10% by mass, and even more preferably 0.2 to 5% by mass.

[Liquid crystal compound]
The liquid crystal compound contained in the liquid crystal composition of the present invention is not particularly limited, and conventionally known liquid crystal compounds can be used.
Generally, liquid crystal compounds can be classified into rod-shaped type and disk-shaped type according to their shape. Furthermore, there are small molecule and high molecular types, respectively. A polymer generally refers to a molecule having a degree of polymerization of 100 or more (Polymer Physics / Phase Transition Dynamics, Masao Doi, p. 2, Iwanami Shoten, 1992).
In the present invention, any liquid crystal compound can be used, but it is preferable to use a rod-shaped liquid crystal compound or a discotic liquid crystal compound, and it is more preferable to use a rod-shaped liquid crystal compound.

The liquid crystal compound preferably has a polymerizable group from the viewpoint of immobilizing the orientation of the liquid crystal compound.
As the polymerizable group, a polymerizable group capable of radical polymerization or cationic polymerization is preferable.
As the radically polymerizable group, a generally known radically polymerizable group can be used, and suitable examples thereof include an acryloyloxy group and a methacryloyloxy group. In this case, it is known that the acryloyloxy group is generally faster in terms of the polymerization rate, and the acryloyloxy group is preferable from the viewpoint of improving productivity, but the methacryloyloxy group can also be used as the polymerizable group in the same manner.
As the cationically polymerizable group, a generally known cationically polymerizable group can be used, and specifically, an alicyclic ether group, a cyclic acetal group, a cyclic lactone group, a cyclic thioether group, a spiroorthoester group, and , Vinyloxy group and the like. Of these, an alicyclic ether group or a vinyloxy group is preferable, and an epoxy group, an oxetanyl group, or a vinyloxy group is particularly preferable.
Examples of particularly preferable polymerizable groups include any polymerizable group selected from the group consisting of the groups represented by the above-mentioned formulas (P-1) to (P-20). Of these, acryloyloxy group or methacryloyloxy group is more preferable.

Further, in the present invention, the liquid crystal compound is preferably a liquid crystal compound having reverse wavelength dispersibility because it enables accurate conversion of the light wavelength in a wide wavelength range.
Here, the liquid crystal compound having "reverse wavelength dispersibility" in the present specification measures the in-plane retardation (Re) value at a specific wavelength (visible light range) of a retardation film produced by using the liquid crystal compound. When the measurement wavelength is increased, the Re value becomes equal or higher.

Further, in the present invention, the liquid crystal compound is selected from the group consisting of the groups represented by the following formulas (Ar-1) to (Ar-7) for the purpose of achieving both reverse wavelength dispersibility and light resistance. It is preferable that the compound has one of the aromatic rings.

In the above formulas (Ar-1) to (Ar-7), * represents a bond position, that is, a bond position with a portion other than the aromatic ring contained in the liquid crystal compound.
In addition, Y ¹ , Q ¹ , Q ² , Q ³ , Z ¹ , Z ² , Z ³ , A ³ , A ⁴ , D ⁷ , D ⁸ in the above equations (Ar-1) to (Ar-7). SP ³ , SP ⁴ , L ³ , L ⁴ , Ax, and Ay are Y ¹ , Q ¹ , and Q in the above formulas (M-1) to (M-7) described in the above-mentioned specific compound, respectively. ² , Q ³ , Z ¹ , Z ² , Z ³ , A ³ , A ⁴ , D ⁷ , D ⁸ , SP ³ , SP ⁴ , L ³ , L ⁴ , Ax, and Ay.

In the present invention, the liquid crystal compound is preferably a compound represented by the following formula (I) because it has a high refractive index anisotropy and therefore the optically anisotropic film can be thinned. In the following formula (I), Ar represents any aromatic ring selected from the group consisting of the groups represented by the above-mentioned formulas (Ar-1) to (Ar-7). However, when q1 in the following formula (I) is 2, the plurality of Ars may be the same or different.
L ¹ -SP ¹ -D ^5- (A ¹ ) _a1 -D ^3- (G ¹ ) _g1 -D ^1- [Ar-D ² ] _q1- (G ² ) _g2 -D ^4- (A ² ) _a2- D ⁶ -SP ² -L ² ... (I)

In the above formula (I), a1, a2, g1 and g2 independently represent 0 or 1, respectively. However, at least one of a1 and g1 represents 1, and at least one of a2 and g2 represents 1.
Further, in the above formula (I), q1 represents 1 or 2.
Further, in the above formula (I), D ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ are independently single-bonded or -CO-, -O-, -S-,-, respectively. C (= S)-, -CR ¹ R ^2- , -CR ³ = CR ^4- , -NR ^5- , or a divalent linking group consisting of two or more of these, representing R ¹ to R. ⁵ independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms. However, when q1 is ² , the plurality of D2s may be the same or different.
Further, in the above formula (I), G ¹ and G ² each independently have an aromatic ring having 6 to 20 carbon atoms which may have a substituent or a carbon which may have a substituent. Represents a divalent alicyclic hydrocarbon group of number 5 to 20, and one or more of -CH _2- constituting the alicyclic hydrocarbon group is substituted with -O-, -S- or -NH-. May be.
Further, in the above formula (I), A ¹ and A ² each independently have an aromatic ring having 6 to 20 carbon atoms which may have a substituent, or a carbon which may have a substituent. Represents a divalent alicyclic hydrocarbon group of number 5 to 20, and one or more of -CH _2- constituting the alicyclic hydrocarbon group is substituted with -O-, -S- or -NH-. May be.
Further, in the above formula (I), SP ¹ and SP ² are independently single-bonded, a linear or branched alkylene group having 1 to 12 carbon atoms, or a linear chain having 1 to 12 carbon atoms. Alternatively, a divalent linkage in which one or more of -CH _2- constituting the branched alkylene group is substituted with -O-, -S-, -NH-, -N (Q)-, or -CO-. Represents a group and Q represents a substituent.
Further, in the above formula (I), L ¹ and L ² each independently represent a monovalent organic group, and at least one of L ¹ and L ² represents a polymerizable group. However, when Ar is an aromatic ring represented by the above-mentioned formula (Ar ^- ³ ), at ^least ^one of L1 and L2 and L3 and L4 in the above-mentioned formula (Ar-3) are polymerized. Represents a sex group.

In the above formula (I), a1, a2, g1 and g2 are all preferably 1.
Further, in the above formula (I), q1 is preferably 1.

In the above formula (I), as the divalent linking group represented by one aspect of D ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ , D ⁷ and D in the above formula (M-3) are used. The same as those described in No. ⁸ can be mentioned.
Of these, any of -CO-, -O-, and -CO-O- is preferable.

In the above formula (I), examples of the aromatic ring having 6 to 20 carbon atoms represented by one aspect of G ¹ and G ² include aromatic hydrocarbon rings such as a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthroline ring. Aromatic heterocycles such as a furan ring, a pyrrole ring, a thiophene ring, a pyridine ring, a thiazole ring, and a benzothiazole ring; among them, a benzene ring (for example, a 1,4-phenyl group) is preferable.

In the above formula (I), the divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms represented by one aspect of G ¹ and G ² is preferably a 5-membered ring or a 6-membered ring. The alicyclic hydrocarbon group may be saturated or unsaturated, but a saturated alicyclic hydrocarbon group is preferable. As the divalent alicyclic hydrocarbon group represented by G ¹ and G ² , for example, the description in paragraph [0078] of JP2012-21068A can be referred to, and the content thereof is incorporated in the present specification. ..

In the present invention, G ¹ and G ² in the above formula (I) are preferably cycloalkane rings.
Specific examples of the cycloalkane ring include a cyclohexane ring, a cyclopeptane ring, a cyclooctane ring, a cyclododecane ring, a cyclododecane ring, and the like.
Of these, the cyclohexane ring is preferred, the 1,4-cyclohexylene group is more preferred, and the trans-1,4-cyclohexylene group is even more preferred.

Further, in the above formula (I), G ¹ and G ² may have a substituent having an aromatic ring having 6 to 20 carbon atoms or a divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms. Can be the same as the substituent that Y ¹ in the above formula (Ar-1) may have.

In the above formula (I), the aromatic rings having 6 to 20 or more carbon atoms shown in one aspect of A ¹ and A ² are the same as those described in G ¹ and G ² in the above formula (I). Can be mentioned.
Further, in the above formula (I), as the divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms represented by one aspect of A ¹ and A ² , in G ¹ and G ² in the above formula (I). Examples are similar to those described.
Regarding A ¹ and A ² , the substituents that the aromatic ring having 6 to 20 carbon atoms or the divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms may have are, for example, the above-mentioned substitutions. The same as the group X can be mentioned.

In the above formula (I), the linear or branched alkylene group having 1 to 12 carbon atoms shown in one aspect of SP ¹ and SP ² is described in SP ³ and SP ⁴ in the above formula (M-3). Some are similar to those described.

Examples of the monovalent organic group represented by L ¹ and L ² in the above formula (I) include those similar to those described in L ³ and L ⁴ in the above formula (M-3).

In the above formula (I), examples of the polymerizable group represented by at least one of L ¹ and L ² include the above-mentioned radical polymerization or cationically polymerizable polymerizable group.
Examples of particularly preferable polymerizable groups include any polymerizable group selected from the group consisting of the groups represented by the above-mentioned formulas (P-1) to (P-20). Of these, acryloyloxy group or methacryloyloxy group is more preferable.

In the above formula (I), it is preferable that both L ¹ and L ² in the above formula (I) are polymerizable groups, and are acryloyloxy group or methacryloyloxy group, for the reason that the durability is good. Is more preferable.

Examples of the compound represented by the above formula (I) include the compounds represented by the general formula (1) described in JP-A-2010-084032 (particularly, those described in paragraph numbers [0067] to [0073]. Compounds), compounds represented by the general formula (II) described in JP-A-2016-053709 (particularly, compounds described in paragraph numbers [0036] to [0043]), and JP-A-2016-081035. Examples thereof include the compound represented by the general formula (1) described (particularly, the compound described in paragraph numbers [0043] to [0055]).

Further, as the compound represented by the above formula (I), compounds represented by the following formulas (1) to (22) are preferably mentioned, and specifically, among the following formulas (1) to (22). Examples of K (side chain structure) include compounds having a side chain structure represented by the following K-1-1 to K-8-9.
In addition, "*" shown in the side chain structure represented by the following K-1-1 to K-8-9 represents the bonding position with the aromatic ring.
Further, in the side chain structure represented by K-1-12 or the like below, the group adjacent to the acryloyloxy group and the methacryloyl group, respectively, represents a propylene group (a group in which a methyl group is replaced with an ethylene group), and is a methyl group. Represents a mixture of positional isomers at different positions.

[Other polymerizable compounds]
The liquid crystal composition of the present invention may contain other polymerizable compounds having one or more polymerizable groups in addition to the above-mentioned specific compound and liquid crystal compound.
Here, the polymerizable group of the other polymerizable compound is not particularly limited, and examples thereof include an acryloyl group, a methacryloyl group, a vinyl group, a styryl group, and an allyl group. Among them, it is preferable to have an acryloyl group and a methacryloyl group.

Examples of other polymerizable compounds include the compounds described in paragraphs [0073] to [0074] of JP-A-2016-053709.
Examples of other polymerizable compounds include compounds represented by the formulas (M1), (M2), and (M3) described in paragraphs [0030] to [0033] of JP-A-2014-077068. More specifically, specific examples described in paragraphs [0046] to [0055] of the same publication can be mentioned.
Further, as the other polymerizable compound, those having the structures of the formulas (1) to (3) described in JP-A-2014-198814 can be preferably used, and more specifically, those having the structure of the same publication can be used. ]-[0035], [0042]-[0050], [0056]-[0057] Specific examples described in paragraphs may be mentioned.

When such another polymerizable compound is contained, the content is preferably less than 50% by mass, more preferably 40% by mass or less, based on the mass of the above-mentioned liquid crystal compound, 2 to 2 to. It is more preferably 30% by mass.

[Polymer initiator]
The liquid crystal composition of the present invention preferably contains a polymerization initiator.
The polymerization initiator used is preferably a photopolymerization initiator capable of initiating a polymerization reaction by irradiation with ultraviolet rays.
Examples of the photopolymerization initiator include α-carbonyl compounds (described in US Pat. Nos. 2,376,661 and 236,670), acidoin ethers (described in US Pat. No. 2,448,828), and α-hydrogen-substituted fragrances. Group acidloin compounds (described in US Pat. No. 2,725,512), polynuclear quinone compounds (described in US Pat. Nos. 3,416127 and 2951758), combinations of triarylimidazole dimers and p-aminophenyl ketone (US patent). 3549365 (described in US Pat. No. 3,549,67), aclysine and phenazine compounds (Japanese Patent Laid-Open No. 60-105667, US Pat. No. 4,239,850), oxadiazole compounds (described in US Pat. No. 421,970), acylphosphine. Examples thereof include oxide compounds (described in Japanese Patent Publication No. 63-40799, Japanese Patent Application Laid-Open No. 5-29234, Japanese Patent Application Laid-Open No. 10-95788, Japanese Patent Application Laid-Open No. 10-29997) and the like.
Further, in the present invention, it is also preferable that the polymerization initiator is an oxime-type polymerization initiator, and specific examples thereof are described in paragraphs [0049] to [0052] of International Publication No. 2017/170443. Agents are mentioned.

〔solvent〕
The liquid crystal composition of the present invention preferably contains a solvent from the viewpoint of workability for forming an optically anisotropic film.
Specific examples of the solvent include a ketone solvent (for example, acetone, 2-butanone, methylisobutylketone, cyclohexanone, cyclopentanone, etc.), an ether solvent (for example, dioxane, tetrahydrofuran, etc.), and a cyclic amide solvent. Solvents (eg, N-methylpyrrolidone, N-ethylpyrrolidone, N, N'-dimethylimidazolidinone, etc.), aliphatic hydrocarbon solvents (eg, hexane, etc.), alicyclic hydrocarbon solvents (eg, cyclohexane). Aromatic hydrocarbon solvents (eg toluene, xylene, trimethylbenzene, etc.), halogenated carbon solvents (eg dichloromethane, dichloroethane, dichlorobenzene, chlorotoluene, etc.), ester solvents (eg, methyl acetate, etc.) Ethyl acetate, butyl acetate, etc.), water, alcohol solvent (eg, ethanol, isopropanol, butanol, cyclohexanol, etc.), cellosolve solvent (eg, methyl cellosolve, ethyl cellosolve, etc.), cellosolve acetate solvent, sulfoxide solvent (eg, methyl cellosolve, ethyl cellosolve, etc.) For example, dimethylsulfoxide and the like), chain amide-based solvents (for example, dimethylformamide, dimethylacetamide, etc.) and the like can be mentioned, and these may be used alone or in combination of two or more.

In the present invention, among the above-mentioned solvents, at least one selected from the group consisting of a ketone solvent, an ether solvent and a cyclic amide solvent for the reason that the effect of the present invention for suppressing an increase in filtration pressure becomes apparent. It is preferably a seed solvent.

[Leveling agent]
The liquid crystal composition of the present invention preferably contains a leveling agent from the viewpoint of keeping the surface of the optically anisotropic film smooth and facilitating orientation control.
As such a leveling agent, a fluorine-based leveling agent or a silicon-based leveling agent is preferable because it has a high leveling effect on the amount of addition, and a fluorine-based leveling agent is less likely to cause crying (bloom, bleed). Is more preferable.
Specific examples of the leveling agent include the compounds described in paragraphs [0079] to [0102] of JP-A-2007-069471, and the general formulas described in JP-A-2013-047204. The compound represented by I) (particularly the compound described in paragraphs [0020] to [0032]) and the compound represented by the general formula (I) described in JP-A-2012-211306 (particularly [0022]. -The compound described in paragraph [0029], the liquid crystal alignment promoter represented by the general formula (I) described in JP-A-2002-129162 (particularly [0076] to [0078] and [0082]- Compounds described in paragraph [0084], compounds represented by the general formulas (I), (II) and (III) described in JP-A-2005-09248 (particularly, paragraphs [0092] to [00906]. The compounds described in 1) and the like. In addition, it may also have a function as an orientation control agent described later.

[Orientation control agent]
The liquid crystal composition of the present invention may contain an orientation control agent, if necessary.
The orientation control agent can form various orientation states such as homeotropic orientation (vertical orientation), tilt orientation, hybrid orientation, and cholesteric orientation, in addition to homogenius orientation, and can make a specific orientation state more uniform and more uniform. It can be realized by precise control.

As the orientation control agent that promotes homogenius orientation, for example, a small molecule orientation control agent or a polymer orientation control agent can be used.
Examples of the small molecule orientation control agent include paragraphs [0009] to [0083] of JP-A-2002-20363, paragraphs [0111]-[0120] of JP-A-2006-106662, and JP-A-2012. -The description in paragraphs [0021] to [0029] of the Publication No. 211306 can be referred to, and this content is incorporated in the present specification.
Further, as the polymer orientation control agent, for example, paragraphs [0021] to [0057] of JP-A-2004-198511 and paragraphs [0121]-[0167] of JP-A-2006-106662 are referred to. And this content is incorporated herein by reference.

Examples of the orientation control agent for forming or promoting homeotropic orientation include a boronic acid compound and an onium salt compound, and specifically, paragraphs [0023] to [0032] of JP-A-2008-225281. , Paragraphs [0052] to [0058] of JP2012-208397A, paragraphs [0024] to [0055] of JP2008-026730, and [0043] to [0055] of JP2016-193869. The compounds described in paragraphs and the like can be taken into consideration, the contents of which are incorporated herein by reference.

On the other hand, the cholesteric orientation can be realized by adding a chiral agent to the liquid crystal composition of the present invention, and the turning direction of the cholesteric orientation can be controlled by the direction of the chiral property. The pitch of the cholesteric orientation can be controlled according to the orientation restricting force of the chiral agent.

When the orientation control agent is contained, the content is preferably 0.01 to 10% by mass, more preferably 0.05 to 5% by mass, based on the total solid content mass in the liquid crystal composition. .. When the content is in this range, it is possible to obtain a uniform and highly transparent optically anisotropic film without precipitation, phase separation, orientation defects, etc., while achieving a desired orientation state.
These orientation control agents can further impart a polymerizable functional group, particularly a polymerizable functional group that can be polymerized with the polymerizable liquid crystal compound constituting the liquid crystal composition of the present invention.

[Other ingredients]
The liquid crystal composition of the present invention may contain a component other than the above-mentioned components, for example, a liquid crystal compound other than the above-mentioned polymerizable liquid crystal compound, a surfactant, a tilt angle control agent, an orientation aid, a plasticizer, and the like. And a cross-linking agent and the like.

[Compound]
The compound of the present invention is a compound represented by the above-mentioned formula (II), and is the same as that described as a specific compound in the above-mentioned liquid crystal composition of the present invention.

[Optically anisotropic film]
The optically anisotropic film of the present invention is an optically anisotropic film obtained by polymerizing the above-mentioned liquid crystal composition of the present invention.
Examples of the method for forming the optically anisotropic film include a method of using the liquid crystal composition of the present invention described above to obtain a desired orientation state and then immobilizing the film by polymerization. In particular, in the present invention, it is preferable to form an optically anisotropic film after the above-mentioned liquid crystal composition of the present invention is prepared and then stored.
Here, the polymerization conditions are not particularly limited, but it is preferable to use ultraviolet rays in the polymerization by light irradiation. The irradiation amount is preferably 10 mJ / cm ² to 50 J / cm ² , more preferably 20 mJ / cm ² to 5 J / cm ² , and even more preferably 30 mJ / cm ² to 3 J / cm ² . , 50-1000 mJ / cm ² is particularly preferable. Further, in order to promote the polymerization reaction, it may be carried out under heating conditions.
In the present invention, the optically anisotropic film can be formed on an arbitrary support in the optical film of the present invention described later or on a polarizing element in the polarizing plate of the present invention described later.

The optically anisotropic membrane of the present invention preferably satisfies the following formula (III).
0.50 <Re (450) / Re (550) <1.00 ... (III)
Here, in the above formula (III), Re (450) represents an in-plane lettering of the optically anisotropic film at a wavelength of 450 nm, and Re (550) represents an in-plane letter of the optically anisotropic film at a wavelength of 550 nm. Represents the optics. If the measurement wavelength of the retardation is not specified in the present specification, the measurement wavelength is 550 nm.
The in-plane retardation value is a value measured using light of a measurement wavelength using AxoScan OPMF-1 (manufactured by Optoscience).
Specifically, by inputting the average refractive index ((Nx + Ny + Nz) / 3) and the film thickness (d (μm)) in AxoScan OPMF-1.
Slow phase axial direction (°)
Re (λ) = R0 (λ)
Rth (λ) = ((nx + ny) /2-nz) × d
Is calculated.
Although R0 (λ) is displayed as a numerical value calculated by AxoScan OPMF-1, it means Re (λ).

The optically anisotropic film of the present invention is preferably a positive A plate or a positive C plate, and more preferably a positive A plate.

Here, the positive A plate (positive A plate) and the positive C plate (positive C plate) are defined as follows.
The refractive index in the slow phase axial direction (the direction in which the refractive index in the plane is maximized) in the film plane is nx, the refractive index in the direction orthogonal to the slow phase axis in the plane in the plane is ny, and the refraction in the thickness direction. When the rate is nz, the positive A plate satisfies the relation of the formula (A1), and the positive C plate satisfies the relation of the formula (C1). The positive A plate shows a positive value for Rth, and the positive C plate shows a negative value for Rth.
Equation (A1) nx> ny≈nz
Equation (C1) nz> nx≈ny
In addition, the above-mentioned "≈" includes not only the case where both are completely the same but also the case where both are substantially the same.
“Substantially the same” means that in a positive A plate, for example, (ny-nz) × d (where d is the thickness of the film) is -10 to 10 nm, preferably -5 to 5 nm. It is included in "ny ≈ nz", and when (nx-nz) x d is -10 to 10 nm, preferably -5 to 5 nm, it is also included in "nx ≈ nz". Further, in the positive C plate, for example, when (nx-ny) × d (where d is the thickness of the film) is 0 to 10 nm, preferably 0 to 5 nm, it is also included in “nx≈ny”.

When the optically anisotropic film of the present invention is a positive A plate, Re (550) is preferably 100 to 180 nm, more preferably 120 to 160 nm, from the viewpoint of functioning as a λ / 4 plate. It is more preferably 130 to 150 nm, and particularly preferably 130 to 140 nm.
Here, the "λ / 4 plate" is a plate having a λ / 4 function, and specifically, a function of converting linear polarization of a specific wavelength into circular polarization (or circular polarization into linear polarization). It is a plate having.

[Optical film]
The optical film of the present invention is an optical film having the optically anisotropic film of the present invention.
1A, 1B and 1C (hereinafter, these drawings are abbreviated as "FIG. 1" when no particular distinction is required) are schematic cross-sectional views showing an example of the optical film of the present invention, respectively.
Note that FIG. 1 is a schematic diagram, and the thickness relationship and positional relationship of each layer do not always match the actual ones, and the support, alignment film, and hardcoat layer shown in FIG. 1 all have an arbitrary configuration. It is a member.
The optical film 10 shown in FIG. 1 has a support 16, an alignment film 14, and an optically anisotropic film 12 in this order.
Further, as shown in FIG. 1B, the optical film 10 may have the hard coat layer 18 on the side opposite to the side where the alignment film 14 of the support 16 is provided, and as shown in FIG. 1C, the optical film 10 may have a hard coat layer 18. The hard coat layer 18 may be provided on the side of the optically anisotropic film 12 opposite to the side on which the alignment film 14 is provided.
Hereinafter, various members used in the optical film of the present invention will be described in detail.

[Optically anisotropic film]
The optically anisotropic film of the optical film of the present invention is the above-mentioned optically anisotropic film of the present invention.
In the optical film of the present invention, the thickness of the optically anisotropic film is not particularly limited, but is preferably 0.1 to 10 μm, more preferably 0.5 to 5 μm.

[Support]
As described above, the optical film of the present invention may have a support as a base material for forming an optically anisotropic film.
Such a support is preferably transparent, and specifically, the light transmittance is preferably 80% or more.

Examples of such a support include a glass substrate and a polymer film, and examples of the polymer film material include a cellulose-based polymer; an acrylic-based polymer having an acrylic acid ester polymer such as polymethylmethacrylate and a lactone ring-containing polymer. Polymers; thermoplastic norbornene polymers; polycarbonate polymers; polyester polymers such as polyethylene terephthalate and polyethylene naphthalate; styrene polymers such as polystyrene and acrylonitrile / styrene copolymers (AS resin); polyethylene, polypropylene, ethylene / propylene Polyolefin-based polymers such as polymers; Vinyl chloride-based polymers; Amido-based polymers such as nylon and aromatic polyamides; Imid-based polymers; Examples thereof include vinylidene chloride-based polymers; vinyl alcohol-based polymers; vinyl butyral-based polymers; allylate-based polymers; polyoxymethylene-based polymers; epoxy-based polymers; or polymers in which these polymers are mixed.
Further, the stator described later may also serve as such a support.

In the present invention, the thickness of the support is not particularly limited, but is preferably 5 to 60 μm, more preferably 5 to 30 μm.

[Alignment film]
When the optical film of the present invention has any of the above-mentioned supports, it is preferable that the optical film has an alignment film between the support and the optically anisotropic film. The support described above may also serve as an alignment film.

The alignment film is generally composed of a polymer as a main component. The polymer material for an alignment film has been described in a large number of documents, and a large number of commercially available products are available.
The polymer material used in the present invention is preferably polyvinyl alcohol or polyimide, and its derivatives. Particularly modified or unmodified polyvinyl alcohol is preferable.
For the alignment film that can be used in the present invention, for example, the alignment film described in International Publication No. 01/88574, page 43, lines 24 to 49, line 8; paragraphs [0071] to [00905] of Patent No. 3907735. ] The modified polyvinyl alcohol described in [2]; a liquid crystal alignment film formed by the liquid crystal alignment agent described in JP-A-2012-155308; and the like.

In the present invention, it is also preferable to use a photoalignment film as the alignment film because it is possible to prevent surface deterioration by not contacting the surface of the alignment film when the alignment film is formed.
The photoalignment film is not particularly limited, but is a polymer material such as a polyamide compound or a polyimide compound described in paragraphs [0024] to [0043] of International Publication No. 2005/096041; A liquid crystal alignment film formed by a liquid crystal alignment agent having a photo-oriented group; a trade name LPP-JP265CP manufactured by Polyimide Technologies, etc. can be used.

Further, in the present invention, the thickness of the alignment film is not particularly limited, but from the viewpoint of alleviating the surface irregularities that may exist on the support and forming an optically anisotropic film having a uniform film thickness, 0. It is preferably 01 to 10 μm, more preferably 0.01 to 1 μm, and even more preferably 0.01 to 0.5 μm.

[Hard coat layer]
The optical film of the present invention preferably has a hardcoat layer in order to impart physical strength to the film. Specifically, the hardcourt layer may be provided on the side opposite to the side where the alignment film of the support is provided (see FIG. 1B), and the side where the alignment film of the optically anisotropic film is provided. May have a hardcourt layer on the opposite side (see FIG. 1C).
As the hard coat layer, those described in paragraphs [0190] to [0196] of JP-A-2009-98658 can be used.

[Other optically anisotropic membranes]
The optical film of the present invention may have another optically anisotropic film in addition to the optically anisotropic film of the present invention.
That is, the optical film of the present invention may have a laminated structure of the optically anisotropic film of the present invention and another optically anisotropic film.
Such other optically anisotropic films are optically anisotropic obtained by using the above-mentioned inverse wavelength dispersible liquid crystal compound or other polymerizable compound (particularly, liquid crystal compound) without blending the above-mentioned specific compound. If it is a film, it is not particularly limited.
Here, in general, liquid crystal compounds can be classified into a rod-shaped type and a disk-shaped type according to their shapes. In addition, there are small molecule and high molecular types, respectively. A polymer generally refers to a molecule having a degree of polymerization of 100 or more (Polymer Physics / Phase Transition Dynamics, Masao Doi, p. 2, Iwanami Shoten, 1992). In the present invention, any liquid crystal compound can be used, but it is preferable to use a rod-shaped liquid crystal compound or a discotic liquid crystal compound (disk-shaped liquid crystal compound). Two or more kinds of rod-shaped liquid crystal compounds, two or more kinds of disk-shaped liquid crystal compounds, or a mixture of a rod-shaped liquid crystal compound and a disk-shaped liquid crystal compound may be used. For the immobilization of the above-mentioned liquid crystal compound, it is more preferable to form a rod-shaped liquid crystal compound having a polymerizable group or a disk-shaped liquid crystal compound, and the liquid crystal compound may have two or more polymerizable groups in one molecule. More preferred. When the liquid crystal compound is a mixture of two or more kinds, it is preferable that at least one kind of liquid crystal compound has two or more polymerizable groups in one molecule.
As the rod-shaped liquid crystal compound, for example, those described in claim 1 of JP-A No. 11-513019 and paragraphs [0026] to [0098] of JP-A-2005-289980 can be preferably used, and discotics can be used. As the liquid crystal compound, for example, those described in paragraphs [0020] to [0067] of JP-A-2007-108732 and paragraphs [0013] to [0108] of JP-A-2010-244038 can be preferably used. However, it is not limited to these.

[UV absorber]
The optical film of the present invention preferably contains an ultraviolet (UV) absorber in consideration of the influence of external light (particularly ultraviolet light).
The ultraviolet absorber may be contained in the optically anisotropic film of the present invention, or may be contained in a member other than the optically anisotropic film constituting the optical film of the present invention. As the member other than the optically anisotropic film, for example, a support is preferably mentioned.
As the ultraviolet absorber, any conventionally known agent capable of exhibiting ultraviolet absorption can be used. Among such ultraviolet absorbers, a benzotriazole-based or hydroxyphenyltriazine-based ultraviolet absorber may be used from the viewpoint of obtaining the ultraviolet absorbing ability (ultraviolet blocking ability) used in an image display device because of its high ultraviolet absorbing ability. preferable.
Further, in order to widen the absorption range of ultraviolet rays, two or more kinds of ultraviolet absorbers having different maximum absorption wavelengths can be used in combination.
Specific examples of the ultraviolet absorber include the compounds described in paragraphs [0258] to [0259] of JP2012-18395, paragraphs [0055] to [0105] of JP2007-72163. Examples thereof include the compounds described in.
Further, as commercially available products, Tinuvin 400, Tinuvin 405, Tinuvin 460, Tinuvin 477, Tinuvin 479, Tinuvin 1577 (all manufactured by BASF) and the like can be used.

[Polarizer]
The polarizing plate of the present invention has the above-mentioned optical film of the present invention and a polarizing element.
Further, the polarizing plate of the present invention can be used as a circular polarizing plate when the optically anisotropic film of the present invention described above is a λ / 4 plate (positive A plate).
Further, in the polarizing plate of the present invention, when the above-mentioned optically anisotropic film of the present invention is a λ / 4 plate (positive A plate), the slow axis of the λ / 4 plate and the absorption axis of the substituent described later are used. The angle formed by the light is preferably 30 to 60 °, more preferably 40 to 50 °, further preferably 42 to 48 °, and particularly preferably 45 °.
Here, the "slow phase axis" of the λ / 4 plate means the direction in which the refractive index becomes maximum in the plane of the λ / 4 plate, and the "absorption axis" of the substituent means the direction in which the absorbance is highest. do.

[Polarizer]
The polarizing plate of the polarizing plate of the present invention is not particularly limited as long as it is a member having a function of converting light into a specific linear polarization, and conventionally known absorption-type and reflection-type splitters can be used. ..
As the absorption type polarizing element, an iodine-based polarizing element, a dye-based polarizing element using a dichroic dye, a polyene-based polarizing element, and the like are used. Iodine-based splitters and dye-based splitters include coated and stretched splitters, both of which can be applied, but polarized light produced by adsorbing iodine or a dichroic dye on polyvinyl alcohol and stretching it. Children are preferred.
Further, as a method for obtaining a polarizing element by stretching and dyeing a laminated film in which a polyvinyl alcohol layer is formed on a substrate, Japanese Patent No. 5048120, Japanese Patent No. 5143918, Japanese Patent No. 4691205, and Patent No. 5048120, Patent No. Japanese Patent No. 4751481 and Japanese Patent No. 4751486 can be mentioned, and known techniques for these substituents can also be preferably used.
As the reflective classifier, a splitter in which thin films having different birefringences are laminated, a wire grid type splitter, a carboxylator in which a cholesteric liquid crystal having a selective reflection region and a 1/4 wave plate are combined, and the like are used.
Among them, at least one selected from the group consisting of a polyvinyl alcohol-based resin (a polymer containing _-CH2 -CHOH- as a repeating unit, particularly a polyvinyl alcohol and an ethylene-vinyl alcohol copolymer) in that the adhesion is more excellent. It is preferable that the polymer contains one).

In the present invention, the thickness of the polarizing element is not particularly limited, but is preferably 3 μm to 60 μm, more preferably 5 μm to 30 μm, and even more preferably 5 μm to 15 μm.

[Adhesive layer]
In the polarizing plate of the present invention, an adhesive layer may be arranged between the optically anisotropic film in the optical film of the present invention and the polarizing element.
The pressure-sensitive adhesive layer used for laminating the optically anisotropic film and the stator is, for example, the ratio of the storage elastic modulus G'and the loss elastic modulus G'measured by a dynamic viscoelasticity measuring device (tan δ =). G "/ G') represents a substance having a value of 0.001 to 1.5, and includes so-called adhesives, substances that easily creep, and the like. Examples of the pressure-sensitive adhesive that can be used in the present invention include, but are not limited to, polyvinyl alcohol-based pressure-sensitive adhesives.

[Image display device]
The image display device of the present invention is an image display device having the optical film of the present invention or the polarizing plate of the present invention.
The display element used in the image display device of the present invention is not particularly limited, and examples thereof include a liquid crystal cell, an organic electroluminescence (hereinafter abbreviated as “EL”) display panel, and a plasma display panel.
Of these, a liquid crystal cell and an organic EL display panel are preferable, and a liquid crystal cell is more preferable. That is, the image display device of the present invention is preferably a liquid crystal display device using a liquid crystal cell as a display element and an organic EL display device using an organic EL display panel as a display element, and the liquid crystal display device is preferable. More preferred.

[Liquid crystal display device]
The liquid crystal display device, which is an example of the image display device of the present invention, is a liquid crystal display device having the above-mentioned polarizing plate of the present invention and a liquid crystal cell.
In the present invention, among the polarizing plates provided on both sides of the liquid crystal cell, it is preferable to use the polarizing plate of the present invention as the polarizing plate on the front side, and the polarizing plate of the present invention as the polarizing plate on the front side and the rear side. Is more preferable to use.
The liquid crystal cells constituting the liquid crystal display device will be described in detail below.

<LCD cell>
The liquid crystal cell used in the liquid crystal display device is a VA (Vertical Alignment) mode, an OCB (Optically Compensated Bend) mode, an IPS (In-Plane-Switching) mode, an FFS (Fringe-Field-Switching) mode, or a TN (Tw) mode. The Nematic) mode is preferred, but is not limited to these.
In the liquid crystal cell in the TN mode, the rod-shaped liquid crystal molecules are substantially horizontally oriented when no voltage is applied, and are further twisted to 60 to 120 °. The TN mode liquid crystal cell is most often used as a color TFT liquid crystal display device, and has been described in many documents.
In the VA mode liquid crystal cell, the rod-shaped liquid crystal molecules are substantially vertically oriented when no voltage is applied. In the VA mode liquid crystal cell, (1) a VA mode liquid crystal cell in a narrow sense (1) in which rod-shaped liquid crystal molecules are oriented substantially vertically when no voltage is applied and substantially horizontally when a voltage is applied (Japanese Patent Laid-Open No. 2-). In addition to (described in Japanese Patent Publication No. 176625), (2) a liquid crystal cell (SID97, Digital of technique. Papers (Proceedings) 28 (1997) 845 in which the VA mode is multi-domainized for expanding the viewing angle). ), (3) Liquid crystal cells in a mode (n-ASM mode) in which rod-shaped liquid crystal molecules are substantially vertically oriented when no voltage is applied and twisted and multi-domain oriented when a voltage is applied. (1998)) and (4) SURVIVAL mode liquid crystal cells (announced at LCD International 98) are included. Further, it may be any of PVA (Patternized Vertical Alignment) type, optical alignment type (Optical Alignment), and PSA (Polymer-Stained Alignment). Details of these modes are described in Japanese Patent Application Laid-Open No. 2006-215326 and Japanese Patent Application Laid-Open No. 2008-538819.
In the IPS mode liquid crystal cell, the rod-shaped liquid crystal molecules are oriented substantially parallel to the substrate, and the liquid crystal molecules respond in a plane by applying an electric field parallel to the substrate surface. In the IPS mode, the display is black when no electric field is applied, and the absorption axes of the pair of upper and lower polarizing plates are orthogonal to each other. Methods for reducing leakage light when displaying black in an oblique direction and improving the viewing angle by using an optical compensation sheet are described in JP-A-10-54982, JP-A-11-202323, and JP-A-9-292522. It is disclosed in JP-A-11-133408, JP-A-11-305217, JP-A-10-307291, and the like.

[Organic EL display device]
The organic EL display device, which is an example of the image display device of the present invention, includes, for example, a λ / 4 plate (positive A plate) made of a polarizing element, an optically anisotropic film of the present invention, and an organic EL from the viewing side. A mode having a display panel in this order is preferably mentioned.
Further, the organic EL display panel is a display panel configured by using an organic EL element formed by sandwiching an organic light emitting layer (organic electroluminescence layer) between electrodes (between a cathode and an anode). The configuration of the organic EL display panel is not particularly limited, and a known configuration is adopted.

The present invention will be described in more detail below based on examples. The materials, amounts used, ratios, treatment contents, treatment procedures, etc. shown in the following examples can be appropriately changed as long as they do not deviate from the gist of the present invention. Therefore, the scope of the present invention should not be construed as limiting by the examples shown below.

[Synthesis of specific compound (2-1)]
The specific compound (2-1) was synthesized according to the scheme shown below.

<STEP1>
As shown in the above scheme, 60.0 g of the compound (2-1-a: 4-hydroxybutyl acrylate), 49.3 g of triethylamine, and 0.9 g of BHT (dibutylhydroxytoluene) are added to 120.1 mL of DMAc (dimethylacetamide). , And 114.1 mL of toluene.
Then, the temperature was cooled to 0 ° C., and 50.6 g of mesylate chloride was slowly added dropwise. After completion of the dropping, the mixture was stirred at an internal temperature of 0 ° C. for 1 hour. Then, the temperature was returned to room temperature (23 ° C.), the liquid was separated with dilute hydrochloric acid, and the second liquid separation was carried out with brine to obtain compound (2-1-b).
Toluene solution of the compound (2-1-b) obtained above, 1,1'-bishiguchi hexyl-4,4'-dicarboxylic acid 91.40 g, triethylamine 72.73 g, and dibutylhydroxytoluene 0. 8 g was mixed with 274.2 mL of DMAc and 69.7 mL of toluene. Then, the mixture was heated to an internal temperature of 90 ° C. and reacted for 5 hours. Then, the temperature was returned to room temperature, dilute hydrochloric acid was added, and the mixture was heated to 42 ° C. to separate the liquids. Then, 0.5 g of TEMPO (2,2,6,6-tetramethylpiperidine1-oxyl) and 164.5 mL of toluene were added, and then the liquid was divided twice with an aqueous sodium hydrogen carbonate solution. The obtained solution was added dropwise to hexane to precipitate a solid, to obtain a white solid compound (2-1-c).

<STEP2-1>
10.0 g of the compound (2-1-c) obtained above and 0.6 g of 1-butyl-3-methylimidazolium tetrafluoroborate were mixed with 50 mL of water. Then, 5.2 g of dimethylamine was slowly added dropwise. After completion of the dropping, the mixture was stirred at room temperature (23 ° C.) for 30 minutes. Then, 50 mL of acetonitrile was added, water was removed by azeotropic concentration, and the precipitated solid was filtered to obtain compound (2-1-d).

<STEP2-2>
11.7 g of the compound (2-1-c) obtained above, 13.1 g of the compound (2-1-e), and 0.2 g of BHT (dibutylhydroxytoluene) were mixed with 150 mL of tetrahydrofuran and 50 mL of chloroform. .. Then, 7.6 g of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride and 0.6 g of N, N-dimethyl-4-aminopyridine were added, and the mixture was stirred at room temperature (23 ° C.) for 3 hours. did. Then, 60 mL of ethyl acetate and dilute hydrochloric acid were added, and the liquids were separated. The solution of the obtained organic layer was concentrated and column-purified to obtain a compound (2-1-f).

<STEP3>
5.0 g of the compound (2-1-d) obtained above and 7.2 g of the compound (2-1-f) were mixed with 50 mL of chloroform. Then, 3.4 g of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride and 0.1 g of N, N-dimethyl-4-aminopyridine were added, and the mixture was stirred at room temperature (23 ° C.) for 3 hours. did. Then, the solid was removed by filtration, and the obtained solution was purified by column to obtain the specific compound (2-1).
The ¹ H-NMR (Nuclear Magnetic Resonance) data of the obtained compound (2-1) is shown below.
^{1 1} H-NMR (CDCl ₃ ) δ (ppm) = 0.92 (m, 8H), 1.21-1.29 (m, 12H), 1.61 (m, 8H), 1.74 (m, 8H), 2.21 (m, 4H), 2.50 (m, 2H), 2.76 (m, 8H), 2.86 (s, 6H), 3.88-4.17 (10H), 5.84 (d, 1H), 6.13 (q, 1H), 6.42 (d, 1H), 7.11 (s, 2H)

[Synthesis of specific compound (2-2)]
The specific compound (2-2) was synthesized according to the scheme shown below.

The compound (2-1-c) and the compound (2-1-d) used in the synthesis of the specific compound (2-1) are the compound (2--2-a) and the compound (2-2) shown in the above scheme. As shown in the above scheme, the specific compound (2-2) was obtained by the same method as the synthesis of the specific compound (2-1) except that it was changed to −b).
The ¹ H-NMR data of the obtained specific compound (2-2) is shown below.
^{1 1} H-NMR (CDCl ₃ ) δ (ppm) = 0.92 (m, 4H), 1.21-1.29 (m, 8H), 1.51 (m, 4H), 1.60 (m, 4H), 1.74 (m, 4H), 2.21 (m, 4H), 2.35 (s, 3H), 2.50 (m, 2H), 2.56 (s, 3H), 2. 76 (m, 8H), 2.86 (s, 6H), 3.88-4.17 (14H), 5.84 (d, 1H), 6.13 (q, 1H), 6.42 (d) , 1H), 6.88 (s, 4H), 7.12-7.20 (m, 5H)

[Synthesis of specific compound (2-3)]
Synthesis of specific compound (2-2) except that the compound (2-3-c) shown below was used in place of the compound (2-2-c) used in the synthesis of the specific compound (2-2). The specific compound (2-3) shown below was obtained in the same manner as in the above.

[Synthesis of specific compound (2-4)]
Synthesis of specific compound (2-1) except that the compound (2-4-e) shown below was used in place of the compound (2-1-e) used in the synthesis of the specific compound (2-1). The specific compound (2-4) shown below was obtained in the same manner as in the above.

[Synthesis of specific compound (2-5)]
Synthesis of specific compound (2-1) except that the compound (2-5-e) shown below was used in place of the compound (2-1-e) used in the synthesis of the specific compound (2-1). The specific compound (2-5) shown below was obtained in the same manner as in the above.

[Synthesis of specific compound (2-1-7)]
The compound (2-1-7-a) shown below is used in place of the compound (2-1-d) used in the synthesis of the specific compound (2-1), and the compound (2-1-f) is replaced. The specific compound (2-1-7) shown below was obtained in the same manner as in the synthesis of the specific compound (2-1) except that the compound (2-1-7-b) shown below was used.

[Synthesis of specific compound (2-1-10)]
The specific compound (2-1) is used except that the compound (2-1-10-f) shown below is used in place of the compound (2-1-1) used in the synthesis of the specific compound (2-1). The specific compound (2-1-10) shown below was obtained by the same method as the synthesis of.

[Example 1]
[Manufacturing of optical film]
A polymerizable liquid crystal composition having the following composition was prepared and applied to a glass substrate with a rubbing-treated polyimide alignment film (SE-150 manufactured by Nissan Chemical Industry Co., Ltd.) by spin coating.
The coating film was oriented at the temperatures shown in Table 1 below to form a liquid crystal layer.
Then, the film was cooled to the exposure temperature shown in Table 1 below, and the orientation was fixed by irradiation with ultraviolet rays of 1000 mJ / cm ² , to form an optically anisotropic film, and an optical film was produced.

―――――――――――――――――――――――――――――――――
Polymerizable liquid crystal composition ――――――――――――――――――――――――――――――――――
-The following reverse wavelength dispersible liquid crystal compound (1-1) 14.70 parts by mass-The following specific compound (2-1) 0.30 parts by mass-Photopolymerization initiator (Irgacure 819, manufactured by BASF) 0.45 parts by mass・ The following fluorine-containing compound A 0.12 parts by mass ・ Cyclopentanone 85.00 parts by mass ―――――――――――――――――――――――――――――― ―――

Reverse wavelength dispersible liquid crystal compound (1-1)

Specific compound (2-1)

Fluorine-containing compound A

[Examples 2 to 6]
An optical film was produced in the same manner as in Example 1 except that the reverse wavelength dispersible liquid crystal compound or the specific compound was changed to the compound shown in Table 1 below.
Regarding the specific compound, among the ring structures represented by M in the above formula (II), the maximum absorption wavelength of the aromatic ring represented by the central M is also shown in Table 1 below.

[Comparative Example 1]
An optical film was produced by the same method as in Example 1 except that the blending amount of the reverse wavelength dispersible liquid crystal compound was changed to the mass part shown in Table 1 below and the specific compound was not blended.

[Comparative Example 2]
An optical film was produced by the same method as in Example 6 except that the blending amount of the reverse wavelength dispersible liquid crystal compound was changed to the mass part shown in Table 1 below and the specific compound was not blended.

<Letteration>
With respect to the produced optical film, a retardation value (Re (450)) having a wavelength of 450 nm and a retardation value (Re (550)) having a wavelength of 550 nm were obtained using Axo Scan (OPMF-1, manufactured by Optoscience). It was measured and Re (450) / Re (550) was calculated. These results are shown in Table 1 below.

<Light resistance>
For the produced optical film, set the glass substrate on a xenon irradiator (SX75 manufactured by Suga Test Instruments Co., Ltd.) so that the coating film of the polymerizable liquid crystal composition serves as the irradiation surface, and use a # 275 filter for 200 hours. An irradiation test was conducted.
The Re (550) of the optical film before the test and the Re (550) of the optical film after the test were measured, and the light resistance was evaluated according to the following criteria. The results are shown in Table 1 below.
A: The amount of change in Re (550) after the test with respect to Re (550) before the test is less than 5% of Re (550) before the test. B: Re (550) after the test with respect to Re (550) before the test. The amount of change is 5% or more and less than 15% of Re (550) before the test. C: The amount of change of Re (550) after the test with respect to Re (550) before the test is 15% or more of Re (550) before the test.

<Orientation defect>
The obtained optical film was cut into 10 cm squares, and the number of alignment defects on the screen was visually confirmed using a polarizing microscope (LEXT, manufactured by Olympus Corporation) and evaluated according to the following evaluation criteria. The results are shown in Table 1 below.
(Evaluation criteria for orientation defects)
A: No defects B: 1 to 10 C: 11 to 100 D: Orientation defects occur on the entire surface (> 100)

The structure of the reverse wavelength dispersible liquid crystal compound and the like in Table 1 above is as shown below.

Reverse wavelength dispersible liquid crystal compound (1-1)

Reverse wavelength dispersible liquid crystal compound (1-2)

Specific compound (2-1)

Specific compound (2-2)

Specific compound (2-3)

Specific compound (2-4)

Specific compound (2-5)

From the results shown in Table 1 above, it was found that orientation defects occur in the formed optically anisotropic film when the specific compound is not blended (Comparative Examples 1 and 2).
On the other hand, it was found that when a specific compound is blended together with the liquid crystal compound, the occurrence of orientation defects in the formed optically anisotropic film can be suppressed (Examples 1 to 6). It was also found that the formed optically anisotropic film also had good light resistance.

Claims

A liquid crystal composition containing a liquid crystal compound and a compound represented by the following formula (II).

Here, in the above formula (II),
R 21 and R 22 each independently represent a hydrogen atom or an alkyl group.
R 23 represents a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group.
SP 21 and SP 22 each independently represent a single bond or an alkylene group. However, the hydrogen atom contained in the alkylene group is 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 1 to 20 carbon atoms. It may be substituted with an alkyl group of. Further, among the -CH 2- constituting the alkylene group, one or two or more -CH 2 -that are not adjacent to each other are -O-, -S-, -CO-, -COO-, and -OCO. -, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -CO-NR 24- , -NH-CO-, -NR 25 -CO-, -NH -, -NR 26 -or may be substituted with -C≡C-, and R24 to R26 represent a substituent.
D 21 and D 22 are independently single-bonded or -CO-, -O-, -S-, -C (= S)-, -CR 27 R 28- , -CR 29 = CR 30- , respectively. , -NH-, -NR 31- , or a divalent linking group consisting of two or more of these, and R 27 to R 31 represent substituents.
M represents an aromatic ring, an alicyclic ring, or a heterocycle which may have a substituent.
m represents an integer of 3 or more, and the plurality of Ms may be the same or different from each other, and the plurality of D 22s may be the same or different from each other.
T represents a hydrogen atom, an alkyl group, or a polymerizable group.
The liquid crystal composition according to claim 1, wherein at least one M in the formula (II) represents an aromatic ring having a maximum absorption wavelength at 280 to 420 nm.
Claim 1 or claim 1, wherein at least one M in the formula (II) represents any aromatic ring selected from the group consisting of groups represented by the following formulas (M-1) to (M-7). 2. The liquid crystal composition according to 2.

Here, in the formulas (M-1) to (M-7),
* Represents the bonding position with D 21 or D 22 .
Q 1 represents N or CH.
Q2 represents -S-, -O-, or -N (R 6 )-, and R 6 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
Y 1 has an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, an aromatic heterocyclic group having 3 to 12 carbon atoms which may have a substituent, or a substituent. It represents an alicyclic hydrocarbon group having 6 to 20 carbon atoms, and one or more of -CH 2- constituting the alicyclic hydrocarbon group is -O-, -S- or -NH-. It may be replaced.
Z 1 , Z 2 and Z 3 independently have a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, and a carbon number of carbon atoms. 6 to 20 monovalent aromatic hydrocarbon groups, 6 to 20 carbon atoms monovalent aromatic heterocyclic groups, halogen atoms, cyano groups, nitro groups, -OR 7 , -NR 8 R 9 , -SR 10 , -COOR 11 or -COR 12 , R 7 to R 12 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and Z 1 and Z 2 are bonded to each other and aromatic. A ring may be formed.
A 3 and A 4 each independently represent a group selected from the group consisting of -O-, -N (R 13 )-, -S-, and -CO-, where R 13 is a hydrogen atom or Represents a substituent.
X represents a Group 14-16 non-metal atom to which a hydrogen atom or a substituent may be attached.
D 7 and D 8 are independently single-bonded or -CO-, -O-, -S-, -C (= S)-, -CR 1 R 2- , -CR 3 = CR 4- , -NR 5- , or a divalent linking group consisting of a combination of two or more of these, and R 1 to R 5 are independently hydrogen atoms, fluorine atoms, or carbon atoms 1 to 12. Represents an alkyl group.
SP 3 and SP 4 independently constitute a single bond, a linear or branched alkylene group having 1 to 12 carbon atoms, or a linear or branched alkylene group having 1 to 12 carbon atoms. One or more of -CH 2- represents a divalent linking group substituted with -O-, -S-, -NH-, -N (Q)-, or -CO-, where Q is a substituent. Represents.
L 3 and L 4 each independently represent a monovalent organic group.
Ax represents an organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocycle.
Ay has a hydrogen atom, an alkyl group having 1 to 12 carbon atoms which may have a substituent, or at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocycle. , Represents an organic group having 2 to 30 carbon atoms.
The aromatic ring in Ax and Ay may have a substituent, or Ax and Ay may be bonded to form a ring.
Q3 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms which may have a substituent.
The liquid crystal composition according to any one of claims 1 to 3, wherein T in the formula (II) represents a polymerizable group.
Claims 1 to 4, wherein T in the formula (II) represents any polymerizable group selected from the group consisting of the groups represented by the following formulas (P-1) to (P-20). The liquid crystal composition according to any one of the following items.

Here, in the above equations (P-1) to (P-20), * represents a bonding position with SP 22 .
The liquid crystal composition according to any one of claims 1 to 5, wherein the liquid crystal compound has a reverse wavelength dispersibility.
Any one of claims 1 to 6, wherein the liquid crystal compound is a compound having any aromatic ring selected from the group consisting of groups represented by the following formulas (Ar-1) to (Ar-7). The liquid crystal composition according to the section.

Here, in the above equations (Ar-1) to (Ar-7),
* Represents the bond position.
Q 1 represents N or CH.
Q2 represents -S-, -O-, or -N (R 6 )-, and R 6 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
Y 1 has an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, an aromatic heterocyclic group having 3 to 12 carbon atoms which may have a substituent, or a substituent. It represents an alicyclic hydrocarbon group having 6 to 20 carbon atoms, and one or more of -CH 2- constituting the alicyclic hydrocarbon group is -O-, -S- or -NH-. It may be replaced.
Z 1 , Z 2 and Z 3 independently have a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, and a carbon number of carbon atoms. 6 to 20 monovalent aromatic hydrocarbon groups, 6 to 20 carbon atoms monovalent aromatic heterocyclic groups, halogen atoms, cyano groups, nitro groups, -OR 7 , -NR 8 R 9 , -SR 10 , -COOR 11 or -COR 12 , R 7 to R 12 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and Z 1 and Z 2 are bonded to each other and aromatic. A ring may be formed.
A 3 and A 4 each independently represent a group selected from the group consisting of -O-, -N (R 13 )-, -S-, and -CO-, where R 13 is a hydrogen atom or Represents a substituent.
X represents a Group 14-16 non-metal atom to which a hydrogen atom or a substituent may be attached.
D 7 and D 8 are independently single-bonded or -CO-, -O-, -S-, -C (= S)-, -CR 1 R 2- , -CR 3 = CR 4- , -NR 5- , or a divalent linking group consisting of a combination of two or more of these, and R 1 to R 5 are independently hydrogen atoms, fluorine atoms, or carbon atoms 1 to 12. Represents an alkyl group.
SP 3 and SP 4 independently constitute a single bond, a linear or branched alkylene group having 1 to 12 carbon atoms, or a linear or branched alkylene group having 1 to 12 carbon atoms. One or more of -CH 2- represents a divalent linking group substituted with -O-, -S-, -NH-, -N (Q)-, or -CO-, where Q is a substituent. Represents.
L 3 and L 4 each independently represent a monovalent organic group.
Ax represents an organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocycle.
Ay has a hydrogen atom, an alkyl group having 1 to 12 carbon atoms which may have a substituent, or at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocycle. , Represents an organic group having 2 to 30 carbon atoms.
The aromatic ring in Ax and Ay may have a substituent, or Ax and Ay may be bonded to form a ring.
Q3 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms which may have a substituent.
The liquid crystal composition according to any one of claims 1 to 7, wherein the liquid crystal compound has a polymerizable group.
The liquid crystal composition according to claim 8, wherein the polymerizable group represents any polymerizable group selected from the group consisting of groups represented by the following formulas (P-1) to (P-20).

Here, in the formulas (P-1) to (P-20), * represents a bonding position.
A compound represented by the following formula (II).

Here, in the above formula (II),
R 21 and R 22 each independently represent a hydrogen atom or an alkyl group.
R 23 represents a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group.
SP 21 and SP 22 each independently represent a single bond or an alkylene group. However, the hydrogen atom contained in the alkylene group is 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 1 to 20 carbon atoms. It may be substituted with an alkyl group of. Further, among the -CH 2- constituting the alkylene group, one or two or more -CH 2 -that are not adjacent to each other are -O-, -S-, -CO-, -COO-, and -OCO. -, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -CO-NR 24- , -NH-CO-, -NR 25 -CO-, -NH -, -NR 26 -or may be substituted with -C≡C-, and R24 to R26 represent a substituent.
D 21 and D 22 are independently single-bonded or -CO-, -O-, -S-, -C (= S)-, -CR 27 R 28- , -CR 29 = CR 30- , respectively. , -NH-, -NR 31- , or a divalent linking group consisting of two or more of these, and R 27 to R 31 represent substituents.
M represents an aromatic ring, an alicyclic ring, or a heterocycle which may have a substituent.
m represents an integer of 3 or more, and the plurality of Ms may be the same or different from each other, and the plurality of D 22s may be the same or different from each other.
T represents a hydrogen atom, an alkyl group, or a polymerizable group.
The compound according to claim 10, wherein at least one M in the formula (II) represents an aromatic ring having a maximum absorption wavelength at 280 to 420 nm.
Claim 10 or claim 10, wherein at least one M in the formula (II) represents any aromatic ring selected from the group consisting of the groups represented by the following formulas (M-1) to (M-7). 11. The compound according to 11.

Here, in the formulas (M-1) to (M-7),
* Represents the bonding position with D 21 or D 22 .
Q 1 represents N or CH.
Q2 represents -S-, -O-, or -N (R 6 )-, and R 6 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
Y 1 has an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, an aromatic heterocyclic group having 3 to 12 carbon atoms which may have a substituent, or a substituent. It represents an alicyclic hydrocarbon group having 6 to 20 carbon atoms, and one or more of -CH 2- constituting the alicyclic hydrocarbon group is -O-, -S- or -NH-. It may be replaced.
Z 1 , Z 2 and Z 3 independently have a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, and a carbon number of carbon atoms. 6 to 20 monovalent aromatic hydrocarbon groups, 6 to 20 carbon atoms monovalent aromatic heterocyclic groups, halogen atoms, cyano groups, nitro groups, -OR 7 , -NR 8 R 9 , -SR 10 , -COOR 11 or -COR 12 , R 7 to R 12 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and Z 1 and Z 2 are bonded to each other and aromatic. A ring may be formed.
A 3 and A 4 each independently represent a group selected from the group consisting of -O-, -N (R 13 )-, -S-, and -CO-, where R 13 is a hydrogen atom or Represents a substituent.
X represents a Group 14-16 non-metal atom to which a hydrogen atom or a substituent may be attached.
D 7 and D 8 are independently single-bonded or -CO-, -O-, -S-, -C (= S)-, -CR 1 R 2- , -CR 3 = CR 4- , -NR 5- , or a divalent linking group consisting of a combination of two or more of these, and R 1 to R 5 are independently hydrogen atoms, fluorine atoms, or carbon atoms 1 to 12. Represents an alkyl group.
SP 3 and SP 4 independently constitute a single bond, a linear or branched alkylene group having 1 to 12 carbon atoms, or a linear or branched alkylene group having 1 to 12 carbon atoms. One or more of -CH 2- represents a divalent linking group substituted with -O-, -S-, -NH-, -N (Q)-, or -CO-, where Q is a substituent. Represents.
L 3 and L 4 each independently represent a monovalent organic group.
Ax represents an organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocycle.
Ay has a hydrogen atom, an alkyl group having 1 to 12 carbon atoms which may have a substituent, or at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocycle. , Represents an organic group having 2 to 30 carbon atoms.
The aromatic ring in Ax and Ay may have a substituent, or Ax and Ay may be bonded to form a ring.
Q3 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms which may have a substituent.
The compound according to any one of claims 10 to 12, wherein T in the formula (II) represents a polymerizable group.
Claims 10 to 13, wherein T in the formula (II) represents any polymerizable group selected from the group consisting of the groups represented by the following formulas (P-1) to (P-20). The compound according to any one.

Here, in the above equations (P-1) to (P-20), * represents a bonding position with SP 22 .
An optically anisotropic film obtained by polymerizing the liquid crystal composition according to any one of claims 1 to 9.
The optically anisotropic film according to claim 15, which satisfies the following formula (III).
0.50 <Re (450) / Re (550) <1.00 ... (III)
Here, in the formula (III), Re (450) represents the in-plane retardation of the optically anisotropic film at a wavelength of 450 nm, and Re (550) represents the in-plane retardation of the optically anisotropic film at a wavelength of 550 nm. Represents a letteration.
An optical film having the optically anisotropic film according to claim 15 or 16.
A polarizing plate having the optical film according to claim 17 and a polarizing element.
An image display device having the optical film according to claim 17 or the polarizing plate according to claim 18.