JP6751321B2 - Optically anisotropic film, optical film, polarizing plate and image display device - Google Patents

Description

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

A polymerizable compound exhibiting reverse wavelength dispersibility has features such as accurate conversion of light wavelength in a wide wavelength range, and thin film of a retardation film because of having a high refractive index. Therefore, it is being actively researched. In addition, in this specification, the "reverse wavelength dispersion" polymerizable compound means an in-plane retardation (Re) value at a specific wavelength (visible light range) of a retardation film produced using the same. In this case, the Re value becomes equal or higher as the measurement wavelength increases.
As a polymerizable compound exhibiting reverse wavelength dispersibility, T-type molecular design guidelines are generally adopted. The wavelength of the long axis of the molecule is shortened, and the wavelength of the short axis located in the center of the molecule is increased. Required to do so.
Therefore, it is known to use a cycloalkylene skeleton having no absorption wavelength for the connection between the short-axis skeleton located in the center of the molecule (hereinafter, also referred to as “reverse wavelength dispersion developing part”) and the long-axis of the molecule. (See, for example, Patent Documents 1 to 4).

JP, 2008-273925, A JP, 2010-031223, A International Publication No. 2014/010325 JP, 2016-081035, A

The present inventors have examined the polymerizable compounds described in Patent Documents 1 to 4, and when a polymerizable compound utilizing a cycloalkylene skeleton is used, the optically anisotropic film formed has high temperature and high temperature. It was clarified that there is a problem of durability such as a change in birefringence when exposed to humidity.

Therefore, an object of the present invention is to provide an optically anisotropic film having excellent durability, an optical film using the same, a polarizing plate and an image display device.

As a result of intensive studies to achieve the above-mentioned object, the present inventors have used a polymerizable compound having a reverse wavelength dispersibility and a polymerizable compound in which two or more rod-shaped mesogen structures are linked in one molecule, The inventors have found that the formed optically anisotropic film has good durability, and completed the present invention.
That is, it was found that the above-mentioned problems can be achieved by the following constitution.

[1] An optically anisotropic film obtained by polymerizing a polymerizable composition containing a polymerizable compound represented by the formula (I) described below and a polymerizable compound represented by the formula (II) described below. ..
[2] The optically anisotropic film according to [1], wherein L ¹⁰ in the formula (II) described below is a linking group represented by the formula (L-1) or (L-2) described below.
[3] L ²¹ in the formula (L-1) described below and L ²² in the formula (L-2) described below are each independently —O—, —CH ₂ O—, —OCH ₂ —, —. _{(CH 2) 2 OC (=} O) -, - C (= O) O (CH 2) 2 -, - NH -, - N (CH 3) -, - S -, - C (= O) O- , -OC (= O) -, - OC (= O) O -, - CH 2 C (= O) O -, - OC (= O) CH 2 -, - C (= O) OCH 2 -, - _{CH 2 OC (= O) -} , - CH = CH-C (= O) O-, or is any linking group selected from -OC (= O) group consisting of -CH = CH-, The optically anisotropic film according to [2].
[4] In any one of [1] to [3], L ¹⁰ in the formula (II) described below is a linking group represented by any of the formulas (1) to (10) described below. Optically anisotropic film.
[5] An optical film having the optically anisotropic film according to any one of [1] to [4].
[6] A polarizing plate comprising the optical film according to [5] and a polarizer.
[7] An image display device having the optical film according to [5] or the polarizing plate according to [6].

According to the present invention, it is possible to provide an optically anisotropic film having excellent durability, an optical film using the same, a polarizing plate and an image display device.

FIG. 1A is a schematic sectional view showing an example of the optical film of the present invention. FIG. 1B is a schematic sectional view showing an example of the optical film of the present invention. FIG. 1C is a schematic 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 constituents described below may be made based on a typical embodiment of the present invention, but the present invention is not limited to such an embodiment.
In addition, in this specification, the numerical range represented using "-" means the range which includes the numerical value described before and after "-" as a lower limit and an upper limit.

[Optically anisotropic film]
The optically anisotropic film of the present invention is represented by a polymerizable compound represented by the formula (I) described later (hereinafter, also abbreviated as “polymerizable compound (I)”) and a formula (II) described later. An optically anisotropic film obtained by polymerizing a polymerizable composition containing a polymerizable compound (hereinafter, also abbreviated as “polymerizable compound (II)”).

In the present invention, as described above, by using the polymerizable compound (II) together with the polymerizable compound (I), the durability of the optically anisotropic film formed becomes good.
This is not clear in detail, but the present inventors presume as follows.
First, ester bonds contained in the structures of polymerizable compounds described in Patent Documents 1 to 4, in particular, ester bonds present between the reverse wavelength dispersion manifesting part and the cycloalkylene skeleton are after polymerization, that is, optical differences. Although present even after the formation of the anisotropic film, the present inventors have found that the ester bond is hydrolyzed in a high temperature and high humidity environment, so that the liquid crystal compound immobilized by the polymerizable group is immobilized. It is presumed that a part of this will be free and mobile, and the birefringence will change.
Therefore, in the present invention, by using the polymerizable compound (II) together with the polymerizable compound (I), the crosslink density is improved, and it becomes difficult for moisture to enter the inside of the optically anisotropic layer. It is considered that the durability was improved because the decomposition did not occur easily. In particular, since the polymerizable compound (II) has a plurality of rod-shaped mesogen structures, it is considered that the polymerizable compound (I) is easily incorporated when oriented, and the crosslink density is improved.
Hereinafter, each component of the polymerizable composition used for forming the optically anisotropic film of the present invention will be described in detail.

[Polymerizable compound (I)]
The polymerizable composition forming the optically anisotropic film contains a polymerizable compound (I) represented by the following formula (I).

In the above formula (I), the two cyclohexane rings each represent a trans-1,4-cyclohexylene group, but each cyclohexane ring shows that the direction of the bond is opposite (trans type). Is.
Therefore, the relationship between the bonding direction between the left cyclohexane ring and L ² in the above formula (I) and the bonding direction between the right cyclohexane ring and L ³ is not particularly limited and is represented by the above formula (I). The structure may be any of the structures shown below.

Here, in the formula (I), m and n each independently represent an integer of 1 or 2. In addition, Z ¹ , Z ² , L ¹ and L ^{4 which} are plural depending on the number of m or n may be the same or different from each other.
In the present invention, both m and n are preferably 1 for the reason that the solubility is excellent and the manufacturing suitability is improved.

Further, in the above formula (I), Z ¹ and Z ² are each independently a trans-1,4-cyclohexylene group which may have a substituent or an arylene group which may have a substituent. Alternatively, it represents a heteroarylene group which may have a substituent.

The arylene group is preferably an arylene group having 6 to 20 carbon atoms, and more preferably an arylene group having 6 to 10 carbon atoms. Specific examples of such an arylene group include a 1,4-phenylene group, a naphthalene-2,6-diyl group, and a tetrahydronaphthalene-2,6-diyl group. Among them, 1,4 -Phenylene group is preferred.
The heteroarylene group is preferably a heteroarylene group having 2 to 9 carbon atoms. As such a heteroarylene group, specifically, for example, pyridine ring, quinoline ring, isoquinoline ring, pyrimidine ring, pyrazine ring, thiophene ring, furan ring, oxazole ring, thiazole ring, imidazole ring, pyrazole ring, oxa One hydrogen atom from each of the two carbon atoms constituting the ring structure selected from the group consisting of a diazole ring, a thiadiazole ring, a triazole ring, and a condensed ring formed by condensation thereof. And the groups obtained by removing them.

Further, Z ¹ and Z ² represents trans-1,4-cyclohexylene group, an arylene group or a heteroarylene group having optionally be substituent (hereinafter, may have a "Z ¹ and Z ² Examples of the “substituent”) include an alkyl group, an alkoxy group, a halogen atom and the like.
As the alkyl group, for example, a linear, branched, or cyclic alkyl group having 1 to 18 carbon atoms is preferable, 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.), more preferably an alkyl group having 1 to 4 carbon atoms, and a methyl group or an ethyl group. Is particularly preferable.
As the alkoxy group, for example, an alkoxy group having 1 to 18 carbon atoms is preferable, and 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. It is more preferably an alkoxy group having the number of 1 to 4, and particularly preferably a methoxy group or an ethoxy group.
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 and a chlorine atom are preferable.

In the present invention, Z ¹ and Z ² in the above formula (I) are both preferably an arylene group which may have a substituent, for the reason of exhibiting liquid crystallinity. More preferably, it is a 1,4-phenylene group which may have.

In the formula (I), L ¹ , L ² , L ³ and L ⁴ are each independently a single bond, or —O—, —CH ₂ O—, —OCH ₂ —, —(CH _{2 ) 2 OC (= O) -} , - C (= O) O (CH 2) 2 -, - NH -, - N (CH 3) -, - S -, - C (= O) O -, - OC (= O) -, - OC (= O) O -, - C (= O) N (T 1) -, - N (T 2) C (= O) -, - C (= O) S-, -SC (= O) -, - CH 2 C (= O) O -, - OC (= O) CH 2 -, - CH = CH-C (= O) O -, - OC (= O) -CH =CH-, -CH=N-, -N=CH-, and -N=N- represents any linking group selected from the group consisting of, and T ¹ and T ² are each independently- representing the Sp ³ -R ^3.

In the present invention, L ¹ , L ² , L ³ and L ^{4 in} the above formula (I) are all —C(═O)O— or —for the reason that they are excellent in solubility and production suitability is improved. It is preferably OC(=O)-.

In addition, ^{two structures} of Sp ¹ and Sp ² in the above formula (I) and L ¹ , L ² , L ³ and L ^{4 in} the above formula (I), namely, —C(═O)N( Sp ³ contained in T ¹ and T ² of T ¹ )- and —N(T ² )C(═O)— are each independently a single bond, or a straight chain or branched chain having 1 to 20 carbon atoms. One or more —CH ₂ — constituting the chain alkylene group and the linear or branched alkylene group having 1 to 20 carbon atoms is —O—, —S—, —NH—, —N. _{(CH 3) -, - C} (= O) -, - represents a or -C (= O) or a linking group selected from the group consisting of substituted groups O- - OC (= O).
The linear or branched alkylene group having 1 to 20 carbon atoms (including the alkylene group before substitution) represented by Sp ^{1 to} Sp ³ is the linear or branched chain having 5 to 15 carbon atoms. An alkylene group is preferable, and specific examples thereof include a pentylene group, a hexylene group, an octylene group, and a decylene group.

In the present invention, because of its excellent solubility, Sp ¹ and Sp ² in the above formula (I) are —CH ₂ — of a linear or branched alkylene group having 1 to 20 carbon atoms. one or more -O -, - S -, - NH -, - N (CH 3) -, - C (= O) -, - OC (= O) - or -C (= O) O- substituted Group (linking group) is preferred, and one or more of —CH ₂ — constituting the linear or branched alkylene group having 5 to 15 carbon atoms is —O—, —OC(═O). )- or —C(═O)O— is more preferred as a group (linking group) substituted with —CH ₂ — which constitutes a linear or branched alkylene group having 5 to 15 carbon atoms. -CH which is substituted with one or two of -OC(=O)- or -C(=O)O- and constitutes a linear or branched alkylene group having 5 to 15 carbon atoms. it is more preferably one is substituted by -O- groups (linking group) - _2.

Further, in the above formula (I), R ¹ and R ² are each independently a polymerizable group selected from the group consisting of groups represented by the following formulas (R-1) to (R-5). Represents a group. In the formulas (R-1) to (R-5) below, * represents a bonding position with Sp ¹ or Sp ² .
Of these, R ¹ and R ² in the above formula (I) are both acryloyl groups represented by the following formula (R-1) or the following formula (R-2) from the viewpoint of polymerization suitability. It is preferably a methacryloyl group represented by

Further, two structures of L ¹ , L ² , L ³ and L ^{4 in} the above formula (I), that is, -C(=O)N(T ¹ )- and -N(T ² )C(=O R ³ contained in T ¹ and T ² of —) is a hydrogen atom, or one or more of —CH ₂ — constituting the cycloalkyl group or cycloalkyl group is —O—, —S—, —NH—. _{, -N (CH 3) -,} - C (= O) -, - OC (= O) - or -C (= O) O- substituted radicals, and the above formula (R-1) ~ ( R-5) represents any group selected from the group consisting of groups represented by R-5). In this case, * in the above formulas (R-1) to (R-5) represents a bonding position with Sp ³ .

Further, in the above formula (I), Ar ¹ represents any aromatic ring selected from the group consisting of groups represented by the following formulas (Ar-1) to (Ar-4). In the following formulas (Ar-1) ~ (Ar -4), * 1 denotes the bonding site to the L ^2, * 2 represents a bonding position to L ^3.

Here, in the formula (Ar-1), Q ¹ represents N or CH, Q ² represents —S—, —O—, or —N(R ⁴ )—, and R ⁴ is Represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, Y ¹ represents an aromatic hydrocarbon group having 6 to 12 carbon atoms, which may have a substituent, or an aromatic heterocyclic group having 3 to 12 carbon atoms; Represents a ring group.
Specific examples of the alkyl group having 1 to 6 carbon atoms represented by R ⁴ include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group. Group, n-pentyl group, and n-hexyl group.
Examples of the aromatic hydrocarbon group having 6 to 12 carbon atoms represented by Y ¹ include aryl groups 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 represented by Y ¹ include heteroaryl groups such as thienyl group, thiazolyl group, furyl group and pyridyl group.
Examples of the substituent which Y ¹ may have include the same as the substituents which Z ¹ and Z ² in the above formula (I) may have.

In the formulas (Ar-1) to (Ar-4), Z ³ , Z ⁴ and Z ⁵ are each independently a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, or a carbon atom. Monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, halogen atom, cyano group, nitro group, -NR ⁵ R ⁶ or -SR ⁷ R ^{5 to} R ⁷ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and Z ³ and Z ⁴ may combine with each other to form an aromatic ring.
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 and an 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, methyl group, ethyl group, tert-butyl group. Groups are especially preferred.
Examples of the monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclodecyl group, methylcyclohexyl group, ethylcyclohexyl group. A monocyclic saturated hydrocarbon group such as a group; cyclobutenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, cyclooctenyl group, cyclodecenyl group, cyclopentadienyl group, cyclohexadienyl group, cyclooctadienyl group, cyclodeca group Monocyclic unsaturated hydrocarbon groups such as dienes; bicyclo[2.2.1]heptyl group, bicyclo[2.2.2]octyl group, tricyclo[5.2.1.0 ^2,6 ]decyl group, tricyclo [3.3.1.1 ^3,7] decyl group, tetracyclo [6.2.1.1 ^3,6. 0 ^2,7 ]dodecyl group, adamantyl group and other polycyclic saturated hydrocarbon groups; and the like.
Specific examples of the monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms include phenyl group, 2,6-diethylphenyl group, naphthyl group, biphenyl group, and the like, and 6 to 12 carbon atoms. The aryl group (especially phenyl group) is 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, a chlorine atom and a bromine atom are preferable.
On the other hand, examples of the alkyl group having 1 to 6 carbon atoms represented by R ^{5 to} R ⁷ include, for example, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group. Group, tert-butyl group, n-pentyl group, n-hexyl group and the like.

In addition, in the formula (Ar-2), A ⁴ and A ⁵ are each independently selected from the group consisting of —O—, —N(R ⁸ )—, —S—, and —CO—. R ⁸ represents a hydrogen atom or a substituent.
Examples of the substituent represented by R ⁸ include the same substituents as Z ¹ and Z ² in the above formula (I) may have.

Further, in the above formula (Ar-2), X represents a hydrogen atom or a non-metal atom of Group 14 to 16 to which a substituent may be bonded.
In addition, examples of the non-metal atom of Groups 14 to 16 represented by X include an oxygen atom, a sulfur atom, a nitrogen atom having a substituent, and a carbon atom having a substituent. Examples thereof include the same substituents as Z ¹ and Z ^{2 in} I) may have.

In the formulas (Ar-3) to (Ar-4), Ax has 2 to 30 carbon atoms and has at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles. Represents an organic group.
In the above formulas (Ar-3) to (Ar-4), Ay is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may have a substituent, or an aromatic hydrocarbon ring and aromatic. It 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, and Ax and Ay may combine with each other to form a ring.
Q ³ represents a hydrogen atom or an optionally substituted alkyl group having 1 to 6 carbon atoms.
Examples of Ax and Ay include those described in paragraphs [0039] to [0095] of Patent Document 3 (International Publication WO2014/010325).
The alkyl group having 1 to 6 carbon atoms represented by Q ³ is, for example, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert. -Butyl group, n-pentyl group, and n-hexyl group, and the like, and the substituent is the same as the substituent that Z ¹ and Z ² in the above formula (I) may have. Is mentioned.

Preferred examples of the polymerizable compound represented by the formula (I) are shown below, but the polymerizable compound is not limited to these polymerizable compounds. The 1,4-cyclohexylene groups in the formulas below are all trans-1,4-cyclohexylene groups.

In addition, in said formula, "*" represents a bonding position.

In the present invention, the polymerizable compound represented by the above formula (I) has the above formula because the electronic interaction between liquid crystal molecules makes the optically anisotropic film more durable. A compound in which Ar ^{1 in} (I) is represented by the above formula (Ar-2) is preferable.
Specific examples of such a compound include a polymerizable compound represented by the following formula I-1 (hereinafter abbreviated as “liquid crystal compound I-1”) and a following formula I-2. A polymerizable compound (hereinafter abbreviated as "liquid crystal compound I-2"), a polymerizable compound represented by the following formula I-3 (hereinafter abbreviated as "liquid crystal compound I-3"), Examples thereof include a polymerizable compound represented by I-4 (hereinafter abbreviated as "liquid crystal compound I-4"). The group adjacent to the acryloyloxy group in the following formulas I-1 and I-2 represents a propylene group (a group in which a methyl group is substituted with an ethylene group), and the liquid crystal compounds I-1 and I-2 are It represents a mixture of regioisomers with different positions of the methyl groups. Further, in the following formulas I-1 to I-4, all 1,4-cyclohexylene groups are trans-1,4-cyclohexylene groups.

[Polymerizable compound (II)]
The polymerizable composition forming the optically anisotropic film contains a polymerizable compound (II) represented by the following formula (II).

Here, in the above formula (II), L ¹⁰ represents a divalent or higher valent linking group.
In addition, a represents an integer of 2 to 10, preferably an integer of 2 to 6, more preferably an integer of 2 to 4, and even more preferably 2.
Further, MG represents the following formula (MG-1), and when a is an integer of 2 to 10, a plurality of MGs may be the same or different.

Here, in the formula (MG-1), * represents a bonding position with L ¹⁰ in the formula (II), and r and s each independently represent an integer of 1 to 3. In addition, Z ¹¹ , Z ¹² , L ¹¹ and L ¹² , which are plural depending on the number of r or s, may be the same or different from each other.
In the present invention, both r and s are preferably 1 or 2, and more preferably 2 for the reasons of excellent solubility and improved production suitability.

Further, in the formula (MG-1), A ¹¹ is a trivalent aromatic hydrocarbon group which may have a substituent or a trivalent aromatic heterocyclic group which may have a substituent. Represents.
The trivalent aromatic hydrocarbon group is obtained, for example, by removing one hydrogen atom from each of the three carbon atoms constituting the ring structure of an aromatic hydrocarbon ring such as a benzene ring, a naphthalene ring, and an anthracene ring. And the groups mentioned above.
The trivalent aromatic heterocyclic group includes three carbon atoms constituting a ring structure of an aromatic heterocyclic ring such as a furan ring, a pyrrole ring, a thiophene ring, a pyridine ring, a thiazole ring, a benzothiazole ring and a phenanthroline ring. Examples thereof include groups obtained by removing one hydrogen atom each.
Further, as the substituent that the trivalent aromatic hydrocarbon group and the trivalent aromatic heterocyclic group may have, Z ¹ and Z ² in the above formula (I) may have. The same thing as a substituent is mentioned.

In the present invention, it is preferable that A ¹¹ in the above formula (MG-1) is a trivalent aromatic hydrocarbon group which may have a substituent, for the reason of exhibiting liquid crystallinity. More preferably, it is a group obtained by removing one hydrogen atom from each of the three carbon atoms constituting the benzene ring structure which may have a group.

In addition, in the formula (MG-1), L ¹¹ and L ¹² are each independently a single bond, or —O—, —CH ₂ O—, —OCH ₂ —, —(CH ₂ ) ₂ OC( = O) -, - C ( = O) O (CH 2) 2 -, - NH -, - N (CH 3) -, - S -, - C (= O) O -, - OC (= O) -, - OC (= O) O -, - C (= O) N (T 3) -, - N (T 4) C (= O) -, - C (= O) S -, - SC (= _{O) -, - CH 2 C} (= O) O -, - OC (= O) CH 2 -, - CH = CH-C (= O) O -, - OC (= O) -CH = CH-, -CH = N -, - N = CH-, and, represents any linking group selected from the group consisting of -N = N-, T ³ and T ⁴ are each independently a hydrogen atom or a carbon atoms It represents an alkyl group of 1 to 6.
Specific examples of the alkyl group having 1 to 6 carbon atoms represented by T ³ and T ⁴ include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, Examples thereof include tert-butyl group, n-pentyl group, and n-hexyl group.

In the present invention, both L ¹¹ and L ^{12 in} the above formula (MG-1) are —C(═O)O— or —OC(═O) because of their excellent solubility and improved production suitability. )- is preferred.

In the formula (MG-1), Z ¹¹ and Z ¹² may each independently have a trans-1,4-cyclohexylene group which may have a substituent, or a substituent. It represents an arylene group or a heteroarylene group which may have a substituent.
Examples of the arylene group and the heteroarylene group include those similar to the arylene group and the heteroarylene group represented by Z ¹ and Z ² in the above formula (I).
In addition, examples of the substituent that the arylene group and the heteroarylene group may have include the same substituents that Z ¹ and Z ² in the above formula (I) may have.

In the present invention, Z ¹¹ in the above formula (MG-1) is a trans-1,4-cyclohexylene group or an arylene group which may have a substituent, for the reason of exhibiting liquid crystallinity. Is preferable, and particularly when r is 2, one Z ¹¹ is a trans-1,4-cyclohexylene group and the other Z ¹¹ is an arylene group which may have a substituent (for example, 1, 4-phenylene group) is more preferable.
For the same reason, Z ¹² in the above formula (MG-1) is preferably a trans-1,4-cyclohexylene group or an arylene group which may have a substituent, and particularly, s is 2 When one of the Z ¹² is a trans-1,4-cyclohexylene group, and the other Z ¹² is an arylene group which may have a substituent (for example, a 1,4-phenylene group). Is more preferable.

In the formula (MG-1), Sp ¹¹ and Sp ¹² are each independently a single bond, or a linear or branched alkylene group having 1 to 20 carbon atoms, and 1 to 10 carbon atoms. At least one of —CH ₂ — constituting the linear or branched alkylene group of 20 is —O—, —S—, —NH—, —N(CH ₃ )—, —C(═O) It represents any linking group selected from the group consisting of groups substituted with -, -OC(=O)- or -C(=O)O-.
The straight-chain or branched-chain alkylene group having 1 to 20 carbon atoms (including the alkylene group before substitution) represented by Sp ¹¹ and Sp ¹² is a straight-chain or branched chain having 5 to 15 carbon atoms. An alkylene group is preferable, and specific examples thereof include a pentylene group, a hexylene group, an octylene group, and a decylene group.

In the present invention, because of its excellent solubility, Sp ¹¹ and Sp ^{12 in} the above formula (MG-1) form a linear or branched alkylene group having 1 to 20 carbon atoms —CH _2. - one or more -O of -, - S -, - NH -, - N (CH 3) -, - C (= O) -, - OC (= O) - or -C (= O) O- Is preferably a group (linking group) substituted with, and at least one of —CH ₂ — constituting the linear or branched alkylene group having 5 to 15 carbon atoms is —O—, —OC( It is more preferably a group (linking group) substituted with ═O)— or —C(═O)O—, and —CH that constitutes a linear or branched alkylene group having 5 to 15 carbon atoms. ₂ - one or two of -OC (= O) - substituted or -C (= O) O- in and constitute a straight-chain or branched alkylene group having 5 to 15 carbon atoms More preferably, one of —CH ₂ — is a group (linking group) substituted with —O—.

Further, in the above formula (MG-1), R ¹¹ and R ¹² are each independently selected from the group consisting of hydrogen atoms or groups represented by the following formulas (R-11) to (R-15). Represented by any of the following formulas (R-11) to (R-15) and at least one of R ¹¹ and R ¹² is a polymerizable group. Represents a sexual group. In the formulas (R-11) to (R-15) below, * represents a binding position with Sp ¹¹ or Sp ¹² .
Of these, R ¹¹ and R ^{12 in} the above formula (MG-1) are both acryloyl groups represented by the following formula (R-11) or the following formula (R- It is preferably a methacryloyl group represented by 12).

In the present invention, L ¹⁰ in the above formula (II) is preferably a linking group represented by the following formula (L-1) or (L-2), and is represented by the following formula (L-1). Is more preferable.

Here, in the above formulas (L-1) and (L-2), * represents a bonding position with MG in the above formula (II), a represents an integer of 2 to 10, and 2 to 6 Is preferably an integer of 2, more preferably an integer of 2 to 4, and even more preferably 2.
The plurality of L ²¹ , L ^22, and SP ²² may be the same or different from each other.

Further, in the above formulas (L-1), Sp ²¹ constitutes aliphatic hydrocarbon group having 1 to 20 carbon atoms, cyclic aliphatic hydrocarbon group, and an aliphatic hydrocarbon group having 1 to 20 carbon atoms -CH ₂ - of one or more -O -, - S -, - NH -, - N (CH 3) -, - OC (= O) - or -C (= O) O- substituted radicals Represents a valent linking group selected from the group consisting of
Of these, an aliphatic hydrocarbon group having 1 to 20 carbon atoms is preferable.

The aliphatic hydrocarbon group having 1 to 20 carbon atoms as the a-valent linking group represented by Sp ²¹ is, for example, the same or different carbon atoms constituting the alkane having 1 to 20 carbon atoms, except for a hydrogen atoms. Examples of the resulting group include groups obtained by removing a hydrogen atoms from the same or different carbon atoms constituting the alkene having 1 to 20 carbon atoms.
Specifically, when a in the formula (L-1) is 2, an alkylene group having 1 to 15 carbon atoms is preferable, an alkylene group having 1 to 8 carbon atoms is more preferable, a methylene group, an ethylene group, Propylene group and butylene group are more preferable.
Further, when a in the formula (L-1) is 4, for example, a group obtained by removing one hydrogen atom from each of the four methyl groups constituting the terminal of 2,2-dimethylpropane, 3, A group obtained by removing one hydrogen atom from each of the four methyl groups constituting the end of 3-diethylpentane, and one hydrogen atom being removed from each of the four methyl groups constituting the end of 4,4-dipropylheptane And the groups obtained by the above.

The cycloaliphatic hydrocarbon group as the a-valent linking group represented by Sp ²¹ constitutes a ring such as a monocyclic saturated hydrocarbon ring, a monocyclic unsaturated hydrocarbon ring, or a polycyclic saturated hydrocarbon ring. Groups obtained by removing a hydrogen atoms from the same or different carbon atoms.
Specific examples of the monocyclic saturated hydrocarbon ring include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclodecane, methylcyclohexane, ethylcyclohexane and the like.
Specific examples of the monocyclic unsaturated hydrocarbon ring include cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclooctene, cyclodecene, cyclopentadiene, cyclohexadiene, cyclooctadiene, cyclodecadiene and the like.
Specific examples of the polycyclic saturated hydrocarbon ring include bicyclo[2.2.1]heptane, bicyclo[2.2.2]octane, tricyclo[5.2.1.0 ^2,6 ]. Decane, tricyclo[3.3.1.1 ^3,7 ]decane, tetracyclo[6.2.1.1 ^3,6 ]. 0 ^2,7 ]dodecane, adamantane and the like.

In the formula (L-2), Sp ²² is a single bond, or an aliphatic hydrocarbon group having 1 to 20 carbon atoms, a cycloaliphatic hydrocarbon group, and an aliphatic carbon group having 1 to 20 carbon atoms. of one or more -O - - -CH ₂ constituting the hydrogen radical, - S -, - NH - , - N (CH 3) -, - OC (= O) - or -C (= O) O- Represents a divalent linking group selected from the group consisting of groups substituted with.
Examples of the divalent linking group represented by Sp ²² include the same groups as Sp ²¹ in the case where a in the above formula (L-1) is 2.
Moreover, as Sp ²² , a single bond or an alkylene group having 1 to 15 carbon atoms is preferable, a single bond or an alkylene group having 1 to 8 carbon atoms is more preferable, and a single bond or a methylene group is further preferable.

In the formulas (L-1) and (L-2), L ²¹ and L ²² are each independently a single bond, or —O—, —CH ₂ O—, —OCH ₂ —, —( _{CH 2) 2 OC (= O} ) -, - C (= O) O (CH 2) 2 -, - NH -, - N (CH 3) -, - S -, - C (= O) O-, -OC (= O) -, - OC (= O) O -, - C (= O) N (T 5) -, - N (T 6) C (= O) -, - C (= O) S -, - SC (= O) -, - CH 2 C (= O) O -, - OC (= O) CH 2 -, - C (= O) OCH 2 -, - CH 2 OC (= O) - , -CH = CH-C (= O) O-, and represents any linking group selected from -OC (= O) group consisting of -CH = CH-, T ⁵ and T ⁶ are each Independently, it represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
Specific examples of the alkyl group having 1 to 6 carbon atoms represented by T ⁵ and T ⁶ include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, Examples thereof include tert-butyl group, n-pentyl group, and n-hexyl group.

In the present invention, L ²¹ in the above formula (L-1) and L ²² in the above formula (L-2) are independently —O— and —CH ₂ O— for the reason of being superior in durability. _{, -OCH 2 -, - (CH} 2) 2 OC (= O) -, - C (= O) O (CH 2) 2 -, - NH -, - N (CH 3) -, - S -, - C (= O) O -, - OC (= O) -, - OC (= O) O -, - CH 2 C (= O) O -, - OC (= O) CH 2 -, - C (= _{O) OCH 2 -, - CH} 2 OC (= O) -, - CH = CH-C (= O) O-, and one selected from -OC (= O) group consisting of -CH = CH- It is preferable that it is the linking group.

In the formula (L-2), Ar ²¹ is an a-valent aromatic hydrocarbon group which may have a substituent or an a-valent aromatic heterocyclic group which may have a substituent. Represents.
Examples of the a-valent aromatic hydrocarbon group include a hydrogen atom from a carbon atoms constituting the ring structure of an aromatic hydrocarbon ring such as a benzene ring, a naphthalene ring, an anthracene ring, a triphenylene ring, and a fluorene ring. The groups obtained by removing one by one are mentioned.
The a-valent aromatic heterocyclic group is a ring of an aromatic heterocyclic ring such as a furan ring, a pyrrole ring, a thiophene ring, a pyridine ring, a thiazole ring, a benzothiazole ring, an oxadiazole ring, a thiazolothiazole ring or a phenanthroline ring. Examples thereof include groups obtained by removing one hydrogen atom from each of a carbon atoms constituting the structure.
Further, as the substituent that the a-valent aromatic hydrocarbon group and the a-valent aromatic heterocyclic group may have, Z ¹ and Z ² in the above formula (I) may have. The same thing as a substituent is mentioned.

In the present invention, L ¹⁰ in the above formula (II) is a linking group represented by any one of the following formulas (1) to (10) for the reason that the durability is superior and the production suitability is improved. Is preferred. Among them, a linking group represented by any one of the following formulas (1), (3) to (5) and (8) to (10) is more preferable, and in the following formula (1) or (9) The linking group represented is more preferable.

Here, in the above formulas (1) to (10), * represents a bonding position with MG in the above formula (II).
Moreover, b in the said Formula (1) represents the integer of 2-20, and c in the said Formula (2) represents the integer of 1-3.

[Other polymerizable compounds]
The polymerizable composition forming the optically anisotropic film is, in addition to the polymerizable compound (I) represented by the above formula (I) and the polymerizable compound (II) represented by the above formula (II), It may contain other polymerizable compounds.
Here, the polymerizable group contained in 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. Of these, an acryloyl group or a methacryloyl group is preferable.

In the present invention, from the reason that the durability of the optically anisotropic film is further improved, another polymerizable compound having 2 to 4 polymerizable groups is preferable, and another polymerizable compound having 2 polymerizable groups is preferable. It is more preferable that the compound is a polar compound.

Examples of such other polymerizable compounds include compounds represented by 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 publication can be mentioned.

[Polymerization initiator]
The polymerizable composition forming the optically anisotropic film 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 U.S. Pat. Nos. 2,367,661 and 2,367,670), acyloin ethers (U.S. Pat. No. 2,448,828), and α-hydrocarbon-substituted fragrances. Group acyloin compounds (described in U.S. Pat. No. 2,722,512), polynuclear quinone compounds (described in U.S. Pat. Nos. 3,046,127 and 2,951,758), triarylimidazole dimers in combination with p-aminophenyl ketone (U.S. Pat. No. 3,549,367), acridine and phenazine compounds (JP-A-60-105667, US Pat. No. 4,239,850) and oxadiazole compounds (US Pat. No. 4,212,970), acylphosphine. Examples thereof include oxide compounds (described in JP-B-63-40799, JP-B-5-29234, JP-A-10-95788, and JP-A-10-29997).

〔solvent〕
The polymerizable composition forming the optically anisotropic film preferably contains a solvent from the viewpoint of workability in forming the optically anisotropic film.
Specific examples of the solvent include ketones (eg, acetone, 2-butanone, methyl isobutyl ketone, cyclohexanone, etc.), ethers (eg, dioxane, tetrahydrofuran, etc.), aliphatic hydrocarbons (eg, hexane). Etc.), alicyclic hydrocarbons (eg cyclohexane etc.), aromatic hydrocarbons (eg toluene, xylene, trimethylbenzene etc.), halogenated carbons (eg dichloromethane, dichloroethane, dichlorobenzene, chlorotoluene etc.) ), esters (eg, methyl acetate, ethyl acetate, butyl acetate, etc.), water, alcohols (eg, ethanol, isopropanol, butanol, cyclohexanol, etc.), cellosolves (eg, methyl cellosolve, ethyl cellosolve, etc.), cellosolve Examples thereof include acetates, sulfoxides (eg, dimethylsulfoxide, etc.), amides (eg, dimethylformamide, dimethylacetamide, etc.), etc. These may be used alone or in combination of two or more. ..

[Method for forming optically anisotropic film]
In the present invention, the method for forming the optically anisotropic film includes, for example, the above-mentioned polymerizable compound (I) and polymerizable compound (II) and any other polymerizable compound, a polymerization initiator and a solvent. A method in which the polymerizable composition is used to bring the polymer into a desired alignment state and then to be immobilized by polymerization may be used.
Here, the polymerization conditions are not particularly limited, but it is preferable to use ultraviolet rays in the polymerization by light irradiation. Irradiation amount is preferably ^{10mJ / cm 2 ~50J / cm 2} , more preferably ^{20mJ / cm 2 ~5J / cm 2} , more preferably 30mJ / cm ² ~3J / cm ² , 50 to 1000 mJ/cm ² is particularly preferable. Further, in order to accelerate the polymerization reaction, it may be carried out under heating conditions.
In the present invention, the optically anisotropic film can be formed on any support of the optical film of the present invention described later or on the polarizer of the polarizing plate of the present invention described later.

[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” unless otherwise required) are schematic cross-sectional views showing an example of the optical film of the present invention.
Note that FIG. 1 is a schematic diagram, and the relationship of the thickness of each layer, the positional relationship, and the like do not always match the actual ones, and the support, the alignment film, and the hard coat layer shown in FIG. 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, the optical film 10 may have a hard coat layer 18 on the side of the support 16 opposite to the side where the alignment film 14 is provided, as shown in FIG. 1B, and as shown in FIG. 1C, A 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-described 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]
The optical film of the present invention may have a support as a base material for forming an optically anisotropic film, as described above.
Such a support is preferably transparent, and specifically has a light transmittance of 80% or more.

Examples of such a support include a glass substrate and a polymer film, and examples of the material of the polymer film include a cellulose-based polymer; an acrylic-based polymer having an acrylic ester polymer such as polymethylmethacrylate and a lactone ring-containing polymer. Polymers: thermoplastic norbornene-based polymers; polycarbonate-based polymers; polyester-based polymers such as polyethylene terephthalate and polyethylene naphthalate; styrene-based polymers such as polystyrene, acrylonitrile-styrene copolymer (AS resin); polyethylene, polypropylene, ethylene-propylene copolymer Polyolefin polymers such as polymers; vinyl chloride polymers; amide polymers such as nylon and aromatic polyamide; imide polymers; sulfone polymers; polyether sulfone polymers; polyether ether ketone polymers; polyphenylene sulfide polymers Vinylidene chloride-based polymers; vinyl alcohol-based polymers; vinyl butyral-based polymers; arylate-based polymers; polyoxymethylene-based polymers; epoxy-based polymers; or polymers obtained by mixing these polymers.
Further, a polarizer described below 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 invention has any of the above-mentioned supports, it preferably has an alignment film between the support and the optically anisotropic film. The above-mentioned support may also serve as an alignment film.

The alignment film generally contains a polymer as a main component. The polymer material for the alignment film is described in many documents, and many commercial products can be obtained.
The polymer material used in the present invention is preferably polyvinyl alcohol or polyimide, and derivatives thereof. Modified or unmodified polyvinyl alcohol is particularly preferable.
Regarding the alignment film usable in the present invention, for example, the alignment film described in WO 01/88574, page 43, line 24 to page 49, line 8; paragraphs [0071] to [0095 of Japanese Patent No. 3907735. ], a modified polyvinyl alcohol; a liquid crystal alignment film formed by the liquid crystal alignment agent described in JP 2012-155308 A; and the like.

In the present invention, it is also preferable to use a photo-alignment film as the alignment film, because it is possible to prevent the deterioration of the surface state by not contacting the surface of the alignment film when forming the alignment film.
The photo-alignment film is not particularly limited, but a polymer material such as a polyamide compound or a polyimide compound described in paragraphs [0024] to [0043] of International Publication No. 2005/096041; described in JP 2012-155308 A. A liquid crystal alignment film formed by a liquid crystal alignment agent having a photo-alignment group as described above; a product name LPP-JP265CP manufactured by Rolic technologies, or the like can be used.

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

[Hard coat layer]
The optical film of the present invention preferably has a hard coat layer in order to impart physical strength to the film. Specifically, a hard coat layer may be provided on the side of the support opposite to the side on which the alignment film is provided (see FIG. 1B). May have a hard coat 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 films]
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 film is an optically anisotropic film obtained by using only one of the polymerizable compound (I) and the polymerizable compound (II) described above, and the other polymerizable films described above. There is no particular limitation as long as it is an optically anisotropic film obtained by using a compound (particularly, a liquid crystal compound).
Here, in general, the liquid crystal compound can be classified into a rod-shaped type and a disc-shaped type according to its shape. Furthermore, there are low-molecular type and high-molecular type respectively. A polymer generally means a polymer 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 crystalline compound can be used, but it is preferable to use a rod-shaped liquid crystalline compound or a discotic liquid crystalline compound (discotic liquid crystalline compound). Two or more rod-shaped liquid crystalline compounds, two or more discotic liquid crystalline compounds, or a mixture of rod-shaped liquid crystalline compounds and discotic liquid crystalline compounds may be used. In order to immobilize the above-mentioned liquid crystalline compound, it is more preferable to form it by using a rod-shaped liquid crystalline compound or a discotic liquid crystalline compound having a polymerizable group, and the liquid crystalline compound has two polymerizable groups in one molecule. It is more preferable to have the above. 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-11-513019 or paragraphs [0026] to [0098] of JP-A-2005-289980 can be preferably used, and disco As the tick liquid crystalline compound, for example, those described in paragraphs [0020] to [0067] of JP2007-108732A and paragraphs [0013] to [0108] of JP2010-244038A are preferably used. However, the present invention is not limited to these.

[UV absorber]
The optical film of the present invention preferably contains an ultraviolet absorber in consideration of the influence of external light (particularly, ultraviolet rays), and more preferably contains the ultraviolet absorber in the support.

As the ultraviolet absorber, any known ultraviolet absorber can be used as long as it can exhibit ultraviolet absorbability. Among such UV absorbers, benzotriazole-based or hydroxyphenyltriazine-based UV absorbers are preferable because they have high UV-absorbing properties and obtain the UV-absorbing ability (UV-cutting ability) used in electronic image display devices. Further, in order to widen the absorption width of ultraviolet rays, two or more kinds of ultraviolet absorbers having different maximum absorption wavelengths can be used in combination.

[Polarizer]
The polarizing plate of the present invention has the above-mentioned optical film of the present invention and a polarizer.

[Polarizer]
The polarizer included in 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 specific linearly polarized light, and a conventionally known absorption type polarizer and reflection type polarizer can be used. ..
Examples of the absorption-type polarizer include iodine-based polarizers, dye-based polarizers using dichroic dyes, and polyene-based polarizers. Iodine-based polarizers and dye-based polarizers include coating-type polarizers and stretch-type polarizers, both of which can be applied. Polarized light produced by adsorbing iodine or dichroic dye in polyvinyl alcohol and stretching. A child is preferable.
Further, as a method for obtaining a polarizer by stretching and dyeing a laminated film in which a polyvinyl alcohol layer is formed on a substrate, Patent No. 5048120, Patent No. 5143918, Patent No. 5048120, Patent No. 4,691,205, Japanese Patent No. 4,751,481, and Japanese Patent No. 4,751,486 can be mentioned, and known techniques relating to these polarizers can also be preferably used.
As the reflection type polarizer, a polarizer in which thin films having different birefringence are laminated, a wire grid type polarizer, a polarizer in which a cholesteric liquid crystal having a selective reflection region and a ¼ wavelength plate are combined are used.
Among them, a polyvinyl alcohol-based resin (a polymer containing —CH ₂ —CHOH— as a repeating unit, particularly at least 1 selected from the group consisting of polyvinyl alcohol and an ethylene-vinyl alcohol copolymer, in terms of excellent adhesion. It is preferable that the polarizer includes

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

[Adhesive layer]
In the polarizing plate of the present invention, a pressure-sensitive adhesive layer may be arranged between the optically anisotropic film in the optical film of the present invention and the polarizer.
The pressure-sensitive adhesive layer used for laminating the optically anisotropic film and the polarizer is, for example, a ratio (tan δ= G″/G′) represents a substance having a value of 0.001 to 1.5, and includes so-called adhesives and substances that easily creep. 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, an organic EL display device using an organic EL display panel as a display element, and a liquid crystal display device. More preferable.

[Liquid crystal display device]
A liquid crystal display device which is an example of the image display device of the present invention is a liquid crystal display device including the above-described 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 front polarizing plate, and the polarizing plate of the present invention as the front and rear polarizing plates. Is more preferably used.
The liquid crystal cell that constitutes the liquid crystal display device will be described in detail below.

<Liquid crystal cell>
The liquid crystal cell used in the liquid crystal display device is preferably a VA (Virtual Alignment) mode, an OCB (Optically Compensated Bend) mode, an IPS (In-Plane-Switching) mode, or a TN (Twisted Nematic). It is not limited to.
In the TN mode liquid crystal cell, rod-shaped liquid crystal molecules are substantially horizontally aligned when no voltage is applied, and further twisted and aligned at 60 to 120°. The TN mode liquid crystal cell is most often used as a color TFT liquid crystal display device, and is described in many documents.
In a VA mode liquid crystal cell, rod-shaped liquid crystal molecules are aligned substantially vertically when no voltage is applied. The VA mode liquid crystal cell includes (1) a VA mode liquid crystal cell in a narrow sense in which rod-shaped liquid crystal molecules are aligned substantially vertically when no voltage is applied, and are aligned substantially horizontally when voltage is applied (Japanese Patent Laid-Open No. HEI 2-200,900). 176625 gazette), and (2) liquid crystal cell (SID97, Digest of tech. Papers (preliminary proceedings) 28 (1997) 845) in which the VA mode is multi-domain (MVA mode) for widening the viewing angle. ), (3) A liquid crystal cell of a mode (n-ASM mode) in which rod-like liquid crystal molecules are substantially vertically aligned when no voltage is applied and twisted in multi-domain alignment when a voltage is applied (Proceedings 58-59 of the Japan Liquid Crystal Conference). (1998)) and (4) SURVIVAL mode liquid crystal cell (announced at LCD International 98). Further, any of a PVA (Patterned Vertical Alignment) type, a photo alignment type (Optical Alignment), and a PSA (Polymer-Sustained Alignment) may be used. Details of these modes are described in JP-A-2006-215326 and JP-A-2008-538819.
In the IPS-mode liquid crystal cell, rod-shaped liquid crystal molecules are oriented substantially parallel to the substrate, and the liquid crystal molecules respond in a plane when an electric field parallel to the substrate surface is applied. In the IPS mode, black is displayed when no electric field is applied, and the absorption axes of the pair of upper and lower polarizing plates are orthogonal to each other. A method of reducing leakage light at the time of black display in an oblique direction and improving a viewing angle by using an optical compensation sheet is disclosed in JP-A-10-54982, JP-A-11-202323, and JP-A-9-292522. JP-A-11-133408, JP-A-11-305217, JP-A-10-307291 and the like.

[Organic EL display device]
As an organic EL display device which is an example of the image display device of the present invention, for example, from the viewer side, the polarizing plate of the present invention and a plate having a λ/4 function (hereinafter, also referred to as “λ/4 plate”). And an organic EL display panel in this order are preferred.
Here, the “plate having a λ/4 function” refers to a plate having a function of converting linearly polarized light of a certain specific wavelength into circularly polarized light (or circularly polarized light into linearly polarized light), for example, a λ/4 plate. Examples of the single-layered structure include a stretched polymer film and a retardation film in which an optically anisotropic film having a λ/4 function is provided on a support, and λ/ A specific example of the mode in which the four plates have a multi-layer structure is a broadband λ/4 plate formed by laminating a λ/4 plate and a λ/2 plate.
The organic EL display panel is a display panel configured by using an organic EL element in which an organic light emitting layer (organic electroluminescence layer) is sandwiched between electrodes (between a cathode and an anode). The structure of the organic EL display panel is not particularly limited, and a known structure is adopted.

Hereinafter, the present invention will be described in more detail based on examples. The materials, usage amounts, ratios, processing contents, processing procedures, and the like shown in the following examples can be appropriately changed without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be limitedly interpreted by the following examples.

[Synthesis of Polymerizable Compound II-1]
<Synthesis of Compound II-1a>
Compound II-1a was synthesized according to the following scheme.

Specifically, a mixture of gentisic acid (9.99 g), dibromoethane (5.80 g) and N,N-dimethylacetamide (50 mL) was added with triethylamine (6.89 g) at room temperature (25°C). added. After stirring at 90° C. for 4 hours, the mixture was cooled to room temperature (25° C.), and the organic layer was washed with 1N aqueous hydrochloric acid and saturated aqueous sodium hydrogen carbonate. After drying the organic layer with magnesium sulfate and filtering the desiccant, the solvent was distilled off under reduced pressure.
The obtained concentrate was dissolved in ethyl acetate, hexane was added, and the precipitated solid was collected by filtration to obtain compound II-1a. The weight of the obtained compound II-1a was 8.01 g, and the yield was 77.6%.

<Synthesis of Polymerizable Compound II-1>
Polymerizable compound II-1 was synthesized according to the following scheme. The starting compound II-1b was synthesized in the same manner as the compound I-4C described in paragraphs [0122] to [0125] of JP-A-2016-081035.

Specifically, compound II-1b (7.13 g), ethyl acetate (40 mL), N,N-dimethylacetamide (10 mL), and 2,6-di-t-butyl-4-methylphenol (13 mg). The mixture was cooled to an internal temperature of 5°C or lower, and thionyl chloride (1.89 g) was added dropwise. After stirring at 10°C or lower for 1 hour, compound II-1a (1.00 g) was added to the mixture. Then, N,N-diisopropylethylamine (4.53 g) was added dropwise so that the internal temperature did not exceed 10° C., and N,N-dimethylaminopyridine (10 mg) was added.
Then, after leaving still at room temperature (25 degreeC) all night, the organic layer was wash|cleaned by 1N hydrochloric acid water and saturated sodium hydrogen carbonate solution mL. After drying the organic layer with magnesium sulfate and filtering the desiccant, the solvent was distilled off under reduced pressure.
The obtained crude product was purified by silica gel column chromatography using ethyl acetate-hexane as a solvent to obtain a polymerizable compound II-1. The weight of the resulting polymerizable compound II-1 was 4.12 g, and the yield was 57.9%.
The ¹ H-NMR (nuclear magnetic resonance) of the resulting polymerizable compound II-1 is shown below.
¹ H-NMR (solvent: CDCl ₃ ) σ (ppm): 1.26-1.29 (m, 12H), 1.60-1.69 (m, 16H), 2.25-2.32 (m , 16H), 2.54-2.66 (m, 24H), 2.91-2.95 (m, 8H), 4.12-4.30 (m, 20H), 5.17-5.21. (M, 4H), 5.82-5.86 (m, 4H), 6.08-6.16 (m, 4H), 6.38-6.44 (m, 4H), 7.00 (dd , 8H), 7.10 (d, 2H), 7.22 (d, 8H), 7.32 (dd, 2H), 7.72 (d, 2H).

[Synthesis of Polymerizable Compound II-2]
<Synthesis of Compound II-2a>
Compound II-2a was synthesized in the same manner as compound II-1a except that dibromopropane was used instead of dibromoethane (see the scheme below).
The weight of the obtained compound II-2a was 9.05 g, and the yield was 80.1%.

<Synthesis of Polymerizable Compound II-2>
Polymerizable compound II-2 was synthesized in the same manner as polymerizable compound II-1 except that compound II-2a was used instead of compound II-1a (see scheme below).

The weight of the resulting polymerizable compound II-2 was 4.02 g, and the yield was 40.7%.
The ¹ H-NMR of the resulting polymerizable compound II-2 is shown below.
¹ H-NMR (solvent: CDCl ₃ ) σ (ppm): 1.26-1.29 (m, 12H), 1.64-1.72 (m, 16H), 2.16-2.35 (m , 18H), 2.56-2.67 (m, 24H), 2.91-2.95 (m, 8H), 4.11-4.31 (m, 16H), 4.41 (t, 4H). ), 5.17-5.21 (m, 4H), 5.82-5.86 (m, 4H), 6.07-6.16 (m, 4H), 6.38-6.44 (m). , 4H), 7.00 (d, 8H), 7.09 (d, 2H), 7.22 (d, 8H), 7.32 (dd, 2H), 7.72 (d, 2H).

[Synthesis of Polymerizable Compound II-3]
<Synthesis of Compound II-3a>
Compound II-3a was synthesized in the same manner as compound II-1a except that 1,4-dibromobutane was used instead of dibromoethane (see the scheme below).
The weight of the obtained compound II-3a was 8.95 g, and the yield was 83.2%.

<Synthesis of Polymerizable Compound II-3>
A polymerizable compound II-3 was synthesized in the same manner as the polymerizable compound II-1 except that the compound II-3a was used instead of the compound II-1a (see the scheme below).

The weight of the resulting polymerizable compound II-3 was 3.01 g, and the yield was 78.0%.
The ¹ H-NMR of the resulting polymerizable compound II-3 is shown below.
¹ H-NMR (solvent: CDCl ₃ ) σ (ppm): 1.26-1.29 (m, 12H), 1.61-1.71 (m, 16H), 1.85-1.89 (m , 4H), 2.27-2.35 (m, 16H), 2.55-2.67 (m, 24H), 2.91-2.95 (m, 8H), 4.12-4.33. (M, 20H), 5.17-5.21 (m, 4H), 5.82-5.86 (m, 4H), 6.08-6.16 (m, 4H), 6.38-6. .44 (m, 4H), 7.00 (dd, 8H), 7.10 (d, 2H), 7.22 (d, 8H), 7.32 (dd, 2H), 7.70 (d, 2H)

[Synthesis of Polymerizable Compound II-4]
<Synthesis of Compound II-4a>
Compound II-4a was synthesized according to the following scheme.

Specifically, starting compound II-1b (40.72 g), ethyl acetate (80 mL), N,N-dimethylacetamide (40 mL), and 2,6-di-t-butyl-4-methylphenol (113 mg) The mixture of 1) was cooled to an internal temperature of 5°C or lower, and thionyl chloride (7.43 g) was added dropwise. After stirring for 1 hour at 10° C. or lower, 2,5-dihydroxybenzaldehyde (9.96 g) was added to the mixture. Then, N,N-diisopropylethylamine (16.11 g) was added dropwise so that the internal temperature did not exceed 15°C.
Then, the mixture was stirred at 10° C. or lower for 1.5 hours, and then the organic layer was washed with 50 mL of 1N hydrochloric acid water, 100 mL of distilled water, and 100 mL of saturated sodium bicarbonate water. After drying the organic layer with magnesium sulfate and filtering the desiccant, the solvent was distilled off under reduced pressure.
Hexane was added to the obtained concentrate, and the precipitated solid was collected by filtration to obtain compound II-4a. The weight of the obtained compound II-4a was 13.89 g, and the yield was 49.3%.

<Synthesis of Compound II-4b>
Compound II-4b was synthesized according to the following scheme.

Specifically, in a mixture of compound II-4a (12.89 g), tetrahydrofuran (98 mL), dimethyl sulfoxide (10 mL), and distilled water (196 mL) at room temperature (25° C.), amidosulfuric acid (3. 19 g) and sodium chlorite (2.80 g) were added. The mixture was stirred at room temperature for 1 hour, methanol and distilled water were added to the mixture, and the precipitated solid was collected by filtration to obtain compound II-4b. The weight of the obtained compound II-4b was 11.02 g, and the yield was 84.3%.

<Synthesis of Polymerizable Compound II-4>
Polymerizable compound II-4 was synthesized according to the following scheme.

Specifically, compound II-4b (1.14 g), compound II-4c (50.0 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (213 mg), N,N-dimethyl. A mixture of acetamide (4.5 mL), tetrahydrofuran (4.5 mL), and 2,6-di-t-butyl-4-methylphenol (113 mg) was stirred at room temperature (25°C) for 18 hours. Then, the organic layer was washed with saturated saline. After drying the organic layer with magnesium sulfate and filtering the desiccant, the solvent was distilled off under reduced pressure.
Methanol was added to the obtained concentrate, and the precipitated solid was collected by filtration to obtain a polymerizable compound II-4. The weight of the resulting polymerizable compound II-4 was 165.2 mg, and the yield was 15.3%.
The ¹ H-NMR of the resulting polymerizable compound II-4 is shown below.
¹ H-NMR (solvent: CDCl ₃ ) σ (ppm): 1.16-1.32 (m, 36H), 1.54-1.72 (m, 48H), 1.95-2.38 (m , 48H), 2.52-2.60 (m, 72H), 2.84-3.01 (m, 24H), 4.10-4.29 (m, 48H), 5.17-5.21. (M, 12H), 5.79-5.86 (m, 12H), 6.07-6.16 (m, 12H), 6.36-6.44 (m, 12H), 6.91-7. .02 (m, 24H), 7.12-7.22 (m, 30H), 7.30 (dd, 6H), 7.92 (m, 6H), 8.38-8.49 (m, 6H). )

[Synthesis of Polymerizable Compound II-5]
<Synthesis of Polymerizable Compound II-5>
Polymerizable compound II-5 was synthesized according to the following scheme.

Specifically, compound II-4b (1.00 g), ethyl acetate (6 mL), N,N-dimethylacetamide (1.5 mL), and 2,6-di-t-butyl-4-methylphenol ( 2.3 mg) was cooled to an internal temperature of 5°C or lower, and thionyl chloride (106 mg) was added dropwise. After stirring at 10°C or lower for 1 hour, compound II-5a (67.0 mg) was added to the mixture. Then, N,N-diisopropylethylamine (230 mg) was added dropwise so that the internal temperature did not exceed 15°C.
Then, after stirring at 10° C. or lower for 1 hour, the organic layer was washed with distilled water and saturated sodium bicarbonate water 100 mL. After drying the organic layer with magnesium sulfate and filtering the desiccant, the solvent was distilled off under reduced pressure.
The obtained crude product was purified by silica gel column chromatography using ethyl acetate-hexane as a solvent to obtain a polymerizable compound II-5. The weight of the resulting polymerizable compound II-5 was 460 mg, and the yield was 55.8%.
The ¹ H-NMR of the resulting polymerizable compound II-5 is shown below.
¹ H-NMR (solvent: CDCl ₃ ) σ (ppm): 1.22-1.29 (m, 12H), 1.59-1.70 (m, 16H), 2.21-2.31 (m , 16H), 2.56-2.63 (m, 24H), 2.89-2.95 (m, 8H), 4.12-4.31 (m, 16H), 5.18-5.21. (M, 4H), 5.82-5.87 (m, 4H), 6.09-6.16 (m, 4H), 6.38-6.44 (m, 4H), 7.00-7. 0.03 (m, 8H), 7.14-7.26 (m, 11H), 7.43 (d, 2H), 7.55 (d, 2H), 7.70 (d, 2H), 7. 96 (s, 2H), 8.10 (s, 2H)

[Synthesis of Polymerizable Compound II-6]
Polymerizable compound II-6 was synthesized in the same manner as polymerizable compound II-5, except that compound II-6a was used instead of compound II-5a (see scheme below).

The weight of the resulting polymerizable compound II-6 was 1.23 g, and the yield was 69.8%.
The ¹ H-NMR of the resulting polymerizable compound II-6 is shown below.
¹ H-NMR (solvent: CDCl ₃ ) σ (ppm): 1.26-1.29 (m, 12H), 1.57-1.70 (m, 16H), 2.20-2.30 (m , 16H), 2.56-2.64 (m, 24H), 2.91-2.95 (m, 8H), 4.12-4.31 (m, 16H), 5.19-5.20. (M, 4H), 5.83-5.86 (m, 4H), 6.09-6.16 (m, 4H), 6.39-6.44 (m, 4H), 7.00-7. .05 (m, 14H), 7.20 (d, 2H), 7.22-7.40 (m, 18H), 7.78 (d, 2H), 7.87 (d, 2H).

[Examples 1 to 6]
<Formation of photo-alignment film P-1>
According to Example 1 of JP 2001-141926 A, one side of a polarizer 1 having a film thickness of 20 μm produced by adsorbing iodine on a stretched polyvinyl alcohol film has an example of JP 2012-155308 A. The coating liquid 1 for photo-alignment prepared with reference to the description of 3 was applied using a 2nd bar.
After coating, the solvent was removed by drying to form a photoisomerizable composition layer 1.
The photo-isomerization composition layer 1 thus obtained was irradiated with polarized ultraviolet rays (180 mJ/cm ² , using an ultra-high pressure mercury lamp) to form a photo-alignment film P-1.

<Formation of optically anisotropic layer>
A coating liquid for an optically anisotropic film having the following composition was applied on the photo-alignment film P-1 by a spin coating method to form a liquid crystal composition layer.
The formed liquid crystal composition layer was once heated to 90° C. on a hot plate and then cooled to 60° C. to stabilize the alignment with the smectic A phase (SmA phase).
Then, the temperature was maintained at 60° C., and the orientation was fixed by ultraviolet irradiation (500 mJ/cm ² , using an ultra-high pressure mercury lamp) in a nitrogen atmosphere (oxygen concentration 100 ppm) to form an optically anisotropic layer film with a thickness of 2.0 μm. Then, an optical film was produced.

――――――――――――――――――――――――――――――――――
Coating liquid for optically anisotropic film――――――――――――――――――――――――――――――――――
-Liquid crystal compound I-1 42.25 parts by mass-Liquid crystal compound I-2 42.25 parts by mass-Polymerizable compound (II) 15.50 parts by mass shown in Table 1 below-Polymerization initiator S below -1 (oxime type) 3.00 parts by mass Leveling agent (compound T-1 below) 0.20 parts by mass Methyl ethyl ketone 219.30 parts by mass ――――――――――――――――――― ―――――――――――――――――

[Comparative Examples 1 to 9]
An optical film was produced in the same manner as in Example 1 except that the following polymerizable compounds A-1 to A-9 were used instead of the polymerizable compound II-1.

<Durability>
The optical films produced in each of the above-mentioned Examples and Comparative Examples were laminated on a glass plate with the optically anisotropic film side being the glass side via an adhesive.
Axo Scan (0PMF-1, manufactured by Axometrics) was used to measure the retardation value before and after the durability test, and the residual rate (%) calculated from the following (Formula A) was evaluated by the following index. The results are shown in Table 1 below. As a durability test condition, a test was conducted in which it was left for 5 days in an environment of 85° C. and a relative humidity of 85%.
Formula A: (retardation value after durability test)/(retardation value before durability test)×100 [%]
A: Retardation value remaining rate is 90% or more B: Retardation value remaining rate is 85% or more and less than 90% C: Retardation value remaining rate is 75% or more and less than 85% D: Retardation value remaining rate Is less than 75%

From the results shown in Table 1, it is formed when a polymerizable compound other than the polymerizable compound represented by the above formula (II) is blended as the polymerizable compound to be blended with the polymerizable compound exhibiting the reverse wavelength dispersibility. It was found that the durability of the optically anisotropic film was poor (Comparative Examples 1 to 9).
On the other hand, when the polymerizable compound represented by the above formula (II) is added as a polymerizable compound to be added together with the polymerizable compound exhibiting reverse wavelength dispersion, the durability of the optically anisotropic film formed is good. It was found that the following results were obtained (Examples 1 to 6).
In particular, from the comparison of Examples 1 to 6, it was found that when L ¹⁰ in the above formula (II) was a linking group represented by the above formula (L-1), the durability was better. ..

10 Optical Film 12 Optically Anisotropic Film 14 Alignment Film 16 Support 18 Hard Coat Layer

Claims (8)

An optically anisotropic film obtained by polymerizing a polymerizable composition containing a polymerizable compound represented by the following formula (I) and a polymerizable compound represented by the following formula (II).
Here, in the formula (I), m and n each independently represent an integer of 1 or 2.
Further, Z ¹ and Z ² each independently have a trans-1,4-cyclohexylene group which may have a substituent, an arylene group which may have a substituent or a substituent. Optionally represent a heteroarylene group, a plurality of Z ¹ when m is 2 may be the same or different, and a plurality of Z ² when n is 2 are the same. It may or may not be.
Further, L ¹ Contact and L ⁴ are independently a single bond, _{or, -O -, - CH 2 O} -, - OCH 2 -, - (CH 2) 2 OC (= O) -, - C ( _{= O) O (CH 2)} 2 -, - NH -, - N (CH 3) -, - S -, - C (= O) O -, - OC (= O) -, - OC (= O) O -, - C (= O ) N (T 1) -, - N (T 2) C (= O) -, - C (= O) S -, - SC (= O) -, - CH 2 C (= O) O -, - OC (= O) CH 2 -, - CH = CH-C (= O) O -, - OC (= O) -CH = CH -, - CH = N -, - N = CH-, and, represents any linking group selected from the group consisting of -N = N-, T ¹ and T ² each independently represent a -Sp ³ -R ^3. When m is 2, a plurality of L ¹ may be the same or different, and when n is 2, a plurality of L ⁴ may be the same or different.
In addition, L ² and L ³ each independently represent —C(═O)O— or —OC(═O)—.
In addition, Sp ¹ , Sp ² and Sp ³ are each independently a single bond, or a linear or branched alkylene group having 1 to 20 carbon atoms, and a linear or branched alkylene group having 1 to 20 carbon atoms or One or more of —CH ₂ — constituting the branched alkylene group is —O—, —S—, —NH—, —N(CH ₃ )—, —C(═O)—, —OC(= O)- or -C(=O)O- represents any linking group selected from the group consisting of groups substituted with.
Further, R ¹ and R ² each independently represent any polymerizable group selected from the group consisting of groups represented by the following formulas (R-1) to (R-5).
Further, R ³ is a hydrogen atom, or one or more of —CH ₂ — constituting the cycloalkyl group or cycloalkyl group is —O—, —S—, —NH—, —N(CH ₃ )—, A group substituted with -C(=O)-, -OC(=O)- or -C(=O)O-, and a group represented by the following formulas (R-1) to (R-5). Represents any group selected from the group consisting of:
Ar ¹ represents any aromatic ring selected from the group consisting of groups represented by the following formulas (Ar-1) and (Ar-2).
Here, in the formulas (R-1) to (R-5), * represents a bonding position with Sp ¹ , Sp ² or Sp ³ .
Here, in the formulas (Ar-1) and (Ar-2), *1 represents a bonding position with L ^2, and *2 represents a bonding position with L ³ .
Q ¹ represents N or CH.
Further, Q ² is -S -, - O-, or, -N (R ⁴⁾ - represents, R ⁴ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
Y ¹ represents an aromatic hydrocarbon group having 6 to 12 carbon atoms or an aromatic heterocyclic group having 3 to 12 carbon atoms, which may have a substituent.
Z ³ and Z ⁴ are each independently 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 6 carbon atoms. To 20 monovalent aromatic hydrocarbon groups, halogen atoms, cyano groups, nitro groups, —NR ⁵ R ⁶ or —SR ⁷ , wherein R ^{5 to} R ⁷ are each independently a hydrogen atom or a carbon atom. Representing an alkyl group of the formulas 1 to 6, Z ³ and Z ⁴ may combine with each other to form an aromatic ring.
A ⁴ and A ⁵ each independently represent a group selected from the group consisting of —O—, —N(R ⁸ )—, —S—, and —CO—, and R ⁸ is hydrogen. Represents an atom or a substituent.
Further, X represents a hydrogen atom or a non-metal atom of Group 14 to 16 to which a substituent may be bonded.
Here, in the formula (II), L ¹⁰ represents a divalent or higher valent linking group.
In addition, a represents an integer of 2 to 10.
Further, MG represents the following formula (MG-1), and when a is an integer of 2 to 10, a plurality of MGs may be the same or different.
Here, in the formula (MG-1), * represents a bonding position with L ¹⁰ in the formula (II), and r and s each independently represent an integer of 1 to 3.
A ¹¹ represents a trivalent aromatic hydrocarbon group which may have a substituent or a trivalent aromatic heterocyclic group which may have a substituent.
L ¹¹ and L ¹² are each independently a single bond or —O—, —CH ₂ O—, —OCH ₂ —, —(CH ₂ ) ₂ OC(═O)—, —C(= _{O) O (CH 2) 2} -, - NH -, - N (CH 3) -, - S -, - C (= O) O -, - OC (= O) -, - OC (= O) O -, - C (= O) N (T 3) -, - N (T 4) C (= O) -, - C (= O) S -, - SC (= O) -, - CH 2 C ( = O) O -, - OC (= O) CH 2 -, - CH = CH-C (= O) O -, - OC (= O) -CH = CH -, - CH = N -, - N = CH-, and, represents any linking group selected from the group consisting of -N = N-, T ³ and T ⁴ independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. When r is 2 or 3, a plurality of L ¹¹ may be the same or different, and when s is 2 or 3, a plurality of L ¹² are the same or different. May be.
Z ¹¹ and Z ¹² each independently have a trans-1,4-cyclohexylene group which may have a substituent, an arylene group which may have a substituent or a substituent. Which represent an optionally substituted heteroarylene group, a plurality of Z ¹¹ when r is 2 or 3 may be the same or different, and a plurality of Z ¹² when s is 2 or 3 are , May be the same or different.
In addition, Sp ¹¹ and Sp ¹² are each independently a single bond, or a straight-chain or branched-chain alkylene group having 1 to 20 carbon atoms, and a straight-chain or branched-chain group having 1 to 20 carbon atoms. At least one of —CH ₂ — constituting the alkylene group of —O—, —S—, —NH—, —N(CH ₃ )—, —C(═O)—, and —OC(═O)—. Alternatively, it represents any linking group selected from the group consisting of groups substituted with -C(=O)O-.
R ¹¹ and R ¹² are each independently a hydrogen atom or any polymerizable group selected from the group consisting of groups represented by the following formulas (R-11) to (R-15). And at least one represents the polymerizable group.
Here, in the formulas (R-11) to (R-15), * represents a bonding position with Sp ¹¹ or Sp ¹² . The optically anisotropic film according to claim 1, wherein L ¹⁰ in the formula (II) is a linking group represented by the following formula (L-1) or (L-2).
Here, in the formulas (L-1) and (L-2), * represents a bonding position with MG in the formula (II).
In addition, a represents an integer of 2 to 10.
In addition, Sp ²¹ is an aliphatic hydrocarbon group having 1 to 20 carbon atoms, a cycloaliphatic hydrocarbon group, and one or more of —CH ₂ — constituting an aliphatic hydrocarbon group having 1 to 20 carbon atoms. -O -, - S -, - NH -, - N (CH 3) -, - OC (= O) - or -C (= O) a value which is selected from the group consisting of substituted groups with O- Represents a linking group of.
In addition, Sp ²² constitutes a single bond, or an -CH _2- which forms an aliphatic hydrocarbon group having 1 to 20 carbon atoms, a cycloaliphatic hydrocarbon group, and an aliphatic hydrocarbon group having 1 to 20 carbon atoms. is -O 1 or more -, - S -, - NH -, - N (CH 3) -, - OC (= O) - , or -C (= O) group consisting of substituted groups with O- Represents a divalent linking group selected. The plurality of Sp ²² may be the same or different.
In addition, L ²¹ and L ²² are each independently a single bond, or —O—, —CH ₂ O—, —OCH ₂ —, —(CH ₂ ) ₂ OC(═O)—, —C(= _{O) O (CH 2) 2} -, - NH -, - N (CH 3) -, - S -, - C (= O) O -, - OC (= O) -, - OC (= O) O -, - C (= O) N (T 5) -, - N (T 6) C (= O) -, - C (= O) S -, - SC (= O) -, - CH 2 C ( = O) O -, - OC (= O) CH 2 -, - C (= O) OCH 2 -, - CH 2 OC (= O) -, - CH = CH-C (= O) O-, and , -OC(=O)-CH=CH- represents any linking group selected from the group consisting of, and T ⁵ and T ⁶ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Represent The plurality of L ²¹ may be the same or different, and the plurality of L ²² may be the same or different.
Ar ²¹ represents an a-valent aromatic hydrocarbon group which may have a substituent or an a-valent aromatic heterocyclic group which may have a substituent. L ²¹ in the formula (L-1) and L ²² in the formula (L-2) are each independently -O-, -CH ₂ O-, -OCH ₂ -, -(CH ₂ ) ₂ OC (= O) -, - C (= O) O (CH 2) 2 -, - NH -, - N (CH 3) -, - S -, - C (= O) O -, - OC (= O) -, - OC (= O) O -, - CH 2 C (= O) O -, - OC (= O) CH 2 -, - C (= O) OCH 2 -, - CH 2 OC (= O)-, -CH=CH-C(=O)O-, and -OC(=O)-CH=CH-, which is any linking group selected from the group consisting of. Optically anisotropic film. The optically anisotropic film according to claim 1, wherein L ¹⁰ in the formula (II) is a linking group represented by any of the following formulas (1) to (10). ..
Here, in the formulas (1) to (10), * represents a bonding position with MG in the formula (II).
Further, b in the formula (1) represents an integer of 2 to 20, and c in the formula (2) represents an integer of 1 to 3. L ¹⁰ in the formula (II) is a linking group represented by any of the formulas (2), (6), (7), (8) and (9). Optically anisotropic film. An optical film having the optically anisotropic film according to claim 1. A polarizing plate comprising the optical film according to claim 6 and a polarizer. An image display device comprising the optical film according to claim 6 or the polarizing plate according to claim 7.