WO2024075762A1

WO2024075762A1 - Compound, composition, anisotropic pigment film, and optical element

Info

Publication number: WO2024075762A1
Application number: PCT/JP2023/036161
Authority: WO
Inventors: 奏也小島; 靖志賀; 芳恵 ▲高▼見; 良輔朝戸; 輝恒大澤; 淳一大泉
Original assignee: 三菱ケミカル株式会社
Priority date: 2022-10-04
Filing date: 2023-10-04
Publication date: 2024-04-11

Abstract

This compound is represented by formula (1). (In formula (1), -XA represents a monovalent organic group. -RA1 and -RA2 each independently represent an alkyl group optionally having a substituent group. -RA1 and -RA2 may be integrated and may form a ring, but moieties -RA1 and -RA2 of the ring formed by -RA1 and -RA2 are formed only of a hydrocarbon chain. -A1-, -A2-, -A3-, and -A4- each independently represent a 1,4-phenylene group optionally having a substituent group. n represents 0, 1, or 2. When n represents 2, the multiple occurrences of -A3- may be the same or may be different from each other.)

Description

Compound, composition, anisotropic dye film and optical element

The present invention relates to compounds and compositions that are useful for polarizing films and the like provided in display elements such as light control elements, liquid crystal elements (LCDs), and organic electroluminescence elements (OLEDs). The present invention also relates to anisotropic dye films and optical elements that use the compositions.

In LCDs, linear and circular polarizing films are used to control the optical rotation and birefringence of the display. Circular polarizing films are also used in OLEDs to prevent reflection of external light in bright places.

Conventionally, examples of such polarizing films include a polarizing film made of polyvinyl alcohol (PVA) dyed with low concentration of iodine (iodine-PVA polarizing film) (Patent Document 1).
However, low-concentration iodine-PVA polarizing plates have problems such as the iodine sublimating or deteriorating, causing a change in color, and warping due to relaxation of the stretching of the PVA, depending on the usage environment.

In response to this, it is also known that an anisotropic dye film formed by applying a liquid crystal composition containing a dye functions as a polarizing film (Patent Document 2).

Japanese Patent Application Laid-Open No. 1-105204 JP 2013-210624 A

When using an anisotropic dye film as a polarizer, it is important that the anisotropic dye film has excellent optical performance, particularly a good dichroic ratio, and light resistance, and there is a demand for the development of an anisotropic dye film that has both high optical performance and high light resistance.

The present invention aims to provide a compound and composition that produces an anisotropic dye film that exhibits a high dichroic ratio and has excellent light resistance, an anisotropic dye film obtained from the composition, and an optical element that includes the anisotropic dye film.

The present inventors have discovered that a compound having a specific structure can solve the above problems.
The first aspect of the present invention has the following aspects.

[1-1] A compound represented by the following formula (1).

(In formula (1),
-XA represents a monovalent organic group.
^-RA1 and ^-RA2 each independently represent an alkyl group which may have a substituent. ^-RA1 and ^-RA2 may be joined together to form a ring, but the ^-RA1 and ^-RA2 portions of the ring formed by ^-RA1 and ^-RA2 are formed only by a hydrocarbon chain.
-A ¹ -, -A ² -, -A ³ - and -A ⁴ - each independently represent a 1,4-phenylene group which may have a substituent.
n represents 0, 1, or 2.
When n is 2, multiple -A ³ - may be the same or different.

[1-2] In the formula (1), -XA is a hydrogen atom, -Ra, -O-Ra, -NH-Ra, -C(=O)-Ra, -C(=O)-O-Ra, -C(=O)-NH-Ra, -C(=O)-N(-Rb)-Ra, -O-C(=O)-Ra, -NH-C(=O)-Ra, -N(-Rb)-C(=O)-Ra, or -S-Ra (-Ra and -Rb each independently represent a number of carbon atoms which may have a branch). The compound according to [1-1], which represents an alkyl group having 1 to 15 carbon atoms, a cycloalkyl group having 5 to 14 ring atoms, or an aryl group having 5 to 14 ring atoms, and the alkyl group, cycloalkyl group, and aryl group may each have a substituent. In addition, -Ra and -Rb may together form a ring having 2 to 15 carbon atoms, and the ring may have a substituent.

[1-3] The compound according to [1-1] or [1-2], wherein -RA ¹ and -RA ² in the formula (1) each independently represent an alkyl group having 1 to 10 carbon atoms which may have a substituent.

[1-4] A composition containing a compound represented by the following formula (2) and a polymerizable liquid crystal compound.

(In formula (2),
-XB represents a monovalent organic group.
Each of ^-RB1 and ^-RB2 independently represents an alkyl group which may have a substituent, and ^-RB1 and ^-RB2 may combine together to form a ring.
-B ¹ - and -B ² - each independently represents a 1,4-phenylene group which may have a substituent.
Each of -B ³ - and -B ⁴ - independently represents a divalent aromatic hydrocarbon ring group which may have a substituent.
n represents 0, 1, or 2.
When n is 2, multiple -B ³ - may be the same or different.

[1-5] The composition according to [1-4], in which -B ⁴ - in the formula (2) is a 1,4-phenylene group which may have a substituent.

[1-6] The composition according to [1-4] or [1-5], wherein -B ³ - in the formula (2) is a 1,4-phenylene group which may have a substituent.

[1-7] In the formula (2), -XB is a hydrogen atom, -Ra, -O-Ra, -NH-Ra, -C(=O)-Ra, -C(=O)-O-Ra, -C(=O)-NH-Ra, -C(=O)-N(-Rb)-Ra, -O-C(=O)-Ra, -NH-C(=O)-Ra, -N(-Rb)-C(=O)-Ra, or -S-Ra (-Ra and -Rb each independently represent an optionally branched alkyl group having 1 to 15 carbon atoms). The composition according to any one of [1-4] to [1-6], wherein -Ra represents an alkyl group, a cycloalkyl group having 5 to 14 atoms constituting the ring, or an aryl group having 5 to 14 atoms constituting the ring, and the alkyl group, cycloalkyl group, and aryl group may each have a substituent. In addition, -Ra and -Rb may together form a ring having 2 to 15 carbon atoms, and the ring may have a substituent.

[1-8] The composition according to any one of [1-4] to [1-7], wherein in the formula (2), ^-RB1 and ^-RB2 each independently represent an alkyl group having 1 to 10 carbon atoms which may have a substituent.

[1-9] An anisotropic dye film formed using a composition described in any one of [1-4] to [1-8].

[1-10] An optical element having the anisotropic dye film described in [1-9].

The present inventors have found that the above-mentioned problems can be solved by a composition containing a polymerizable liquid crystal compound and a dye exhibiting specific maximum absorption wavelength characteristics.
The second aspect of the present invention has the following aspects.

[2-1] A composition containing a polymerizable liquid crystal compound and a dye,
A composition in which the maximum absorption wavelength of the dye satisfies the following relation (11):
λ _max2 −λ _max1 <0 (11)
(In formula (11), λ _max1 represents the maximum absorption wavelength of the dye in a solvent, and λ _max2 represents the maximum absorption wavelength of the dye in a dye film formed using the composition.)

[2-2] The composition described in [2-1], in which the dye is an azo dye.

[2-3] The composition according to [2-2], wherein the dye is a compound represented by the following formula (12):
X ²⁰ (-A ²¹ ) _m1 (-N=N-A ²² ) _n1 -N=N-A ²³ -Y ²⁰ (12)
(In formula (12),
-A ²¹ -, -A ²² -, and -A ²³ - each independently represent a divalent group of an aromatic hydrocarbon ring which may have a substituent, or an aromatic heterocycle which may have a substituent;
-X ²⁰ and -Y ²⁰ each independently represent an arbitrary monovalent substituent;
m1 represents 1 or 2;
n1 represents 0, 1, 2, or 3.
When m1 is 2, -A ²¹ - may be the same or different.
When n1 is 2 or 3, -A ²² - may be the same or different.

[2-4] The composition according to [2-3], wherein in the formula (12), -A ²¹ - and -A ²³ - each independently represent a divalent group of an aromatic hydrocarbon ring which may have a substituent.

[2-5] The composition according to [2-3] or [2-4], wherein in the formula (12), -A ²² - is a divalent group of an aromatic hydrocarbon ring which may have a substituent.

[2-6] The composition according to any one of [2-3] to [2-5], wherein in the formula (12), -Y ²⁰ is represented by the following formula (12a):
-N-(R ^y )-R ^x (12a)
(In formula (12a), -R ^x and -R ^y each independently represent an alkyl group or an aryl group which may have a branch, and the alkyl group or aryl group may have a substituent. -R ^x and -R ^y may together form a ring having 2 to 15 carbon atoms together with N, and the ring may have a substituent.)

[2-7] The composition according to any one of [2-1] to [2-6], wherein the polymerizable liquid crystal compound is a low molecular weight polymerizable liquid crystal compound that does not have a copolymer structure.

[2-8] An anisotropic dye film formed using a composition described in any one of [2-1] to [2-7].

[2-9] An optical element having the anisotropic dye film described in [2-8].

The compounds and compositions of the present invention can provide an anisotropic dye film that exhibits a high dichroic ratio and has excellent light resistance.

The present invention will be described in detail below with reference to the embodiments. The present invention is not limited to the following embodiments, and can be modified in various ways within the scope of the present invention.
Hereinafter, the "first invention" and the "second invention" will be collectively referred to as "the present invention."

The anisotropic dye film in the present invention is a dye film having anisotropy in electromagnetic properties in any two directions selected from a total of three directions in a three-dimensional coordinate system including the thickness direction of the anisotropic dye film and any two orthogonal in-plane directions. Examples of the electromagnetic properties include optical properties such as absorption and refraction, and electrical properties such as resistance and capacitance.
Examples of films having optical anisotropy such as absorption and refraction include polarizing films such as linear polarizing films and circular polarizing films, retardation films, and conductive anisotropic dye films. The anisotropic dye film using the compound and composition of the present invention is preferably used as a polarizing film or a conductive anisotropic dye film, and more preferably used as a polarizing film.

In the present invention, the dye is a substance or compound that absorbs at least a part of the wavelengths in the visible light region (350 nm to 800 nm).
Dyes that can be used in the present invention include dichroic dyes. The dichroic dye refers to a dye that has different absorbance in the long axis direction of the molecule and absorbance in the short axis direction. The dye may or may not have liquid crystallinity. The term "liquid crystallinity" refers to the ability to exhibit a liquid crystal phase at any temperature.

[Compound of the first invention]
The compound of the first invention is a compound represented by the following formula (1) (hereinafter, sometimes referred to as "compound (1)").

<Relationship between the structure and effect of compound (1)>
Although the details of the mechanism by which compound (1) exhibits the effects of the first invention are not clear, it is speculated as follows.
By containing the compound (1) having the specific structure represented by formula (1) as a dye, the dye association state in the anisotropic dye film is optimized, and an anisotropic dye film having good optical performance such as a dichroic ratio when used as a polarizer and high light resistance can be obtained.

<-XA>
-XA represents a monovalent organic group.

The organic group of -XA is preferably a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxy group, a carbamoyl group, -Ra, -O-Ra, -NH-Ra, -C(=O)-Ra, -C(=O)-O-Ra, -C(=O)-NH-Ra, -C(=O)-N(-Rb)-Ra, -O-C(=O)-Ra, -NH-C(=O)-Ra, -N(-Rb)-C(=O)-Ra, or -S-Ra (-Ra and -Rb are each independently Each independently represents an alkyl group having 1 to 15 carbon atoms, which may be branched, a cycloalkyl group having 5 to 14 atoms constituting a ring, or an aryl group having 5 to 14 atoms constituting a ring, and the alkyl group, cycloalkyl group, and aryl group may each have a substituent. -Ra and -Rb may together form a ring having 2 to 15 carbon atoms, and the ring may have a substituent.)

In terms of improving the molecular alignment with the polymerizable liquid crystal compound, it is preferable that the monovalent organic group in -XA does not have a polymerizable group, which will be described later. On the other hand, in terms of improving the mechanical strength of the anisotropic dye film, it is preferable that the monovalent organic group in -XA has a polymerizable group, which will be described later.

The alkyl group having 1 to 15 carbon atoms, which may have a branch, the cycloalkyl group having 5 to 14 ring-constituting atoms, and the aryl group having 5 to 14 ring-constituting atoms in -Ra and -Rb each may have a substituent.
Furthermore, one or more methylene groups contained in an alkyl group having 1 to 15 carbon atoms which may have a branch, a cycloalkyl group having 5 to 14 ring atoms, or a ring formed by combining -Ra and -Rb may have a structure in which they are replaced (displaced) by -O-, -S-, -NH-, -N(R ^z )-, -C(═O)-, -C(═O)-O-, -C(═O)-NH-, -CHF-, -CF ₂ -, -CHCl-, or -CCl ₂ -, or may have a structure in which they are replaced by a polymerizable group such as an acryloyloxy group, a methacryloyloxy group, or a glycidyloxy group. Here, R ^z represents a straight-chain or branched alkyl group having 1 to 6 carbon atoms.

Examples of the substituents permitted for the branched alkyl group having 1 to 15 carbon atoms in -Ra and -Rb include -OH, -O-R ^f , -O-C(=O)-R ^f , -NH ₂ , -NH-R ^f , -N(-R ^g )-R ^f , -C(=O)-R ^f , -C(=O)-O-R ^f , -C(=O)-NH ₂ , -C(=O)-NH-R ^f , -C(=O)-N(-R ^g )-R ^f , -SH, -S-R ^f , a sulfamoyl group, a carboxy group, a cyano group, a nitro group, a halogen, etc. Here, -R ^f and -R ^g each independently represent a straight-chain or branched alkyl group having 1 to 15 carbon atoms, preferably 1 to 10 carbon atoms.
One or more methylene groups contained in the linear or branched alkyl group having 1 to 15 carbon atoms may be displaced by -O-, -S-, -NH-, -N(R ^h )-, -C(═O)-, -C(═O)-O-, -C(═O)-NH-, -CHF-, -CF ₂ -, -CHCl-, or -CCl ₂ -, or may be replaced by a polymerizable group such as an acryloyloxy group, a methacryloyloxy group, or a glycidyloxy group. R ^h represents a linear or branched alkyl group having 1 to 6 carbon atoms.
Among these, the substituent permitted for the branched alkyl group having 1 to 15 carbon atoms in -Ra and -Rb is preferably -O- ^Rf , and examples thereof include methoxy, ethoxy, n-propoxy, n-butoxy, n-pentoxy, n-hexoxy, n-heptoxy, n-octoxy, acryloyloxy, methacryloyloxy, and glycidyloxy.

Examples of the substituents permitted for the cycloalkyl group or aryl group having 5 to 14 ring atoms in -Ra and -Rb include -R ⁱ , -OH, -O-R ⁱ , -O-C(=O)-R ⁱ , -NH ₂ , -NH-R ⁱ , -N(-R ^j )-R ⁱ , -C(=O)-R ⁱ , -C(=O)-O-R ⁱ , -C(=O)-NH ₂ , -C(=O)-NH-R ⁱ , -C(=O)-N(-R ^j )-R ⁱ , -SH, -S-R ⁱ , trifluoromethyl group, sulfamoyl group, carboxy group, cyano group, nitro group, and halogen. -R ⁱ and -R ^j each independently represent a straight-chain or branched alkyl group having 1 to 10 carbon atoms, preferably 1 to 5 carbon atoms.

Among these, preferred substituents for the cycloalkyl group or aryl group having 5 to 14 ring-constituting atoms in -Ra and -Rb are -R ⁱ and -O-R ⁱ , and examples thereof include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, methoxy, ethoxy, n-propoxy, n-butoxy, n-pentoxy, n-hexoxy, n-heptoxy, n-octoxy, 2-ethylhexyloxy, 5,5-dimethyl-3-methylhexyloxy, and the like.

Cycloalkane rings of cycloalkyl groups with 5 to 14 ring-constituting atoms of -Ra and -Rb include a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, a cyclooctane ring, a cyclohexene ring, a norbornane ring, a bornane ring, an adamantane ring, a tetrahydronaphthalene ring, and a bicyclo[2.2.2]octane ring.

The aryl group having 5 to 14 ring-constituting atoms of -Ra and -Rb includes a monovalent group of an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
Examples of the aromatic hydrocarbon ring of the monovalent group of the aromatic hydrocarbon ring include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzpyrene ring, a chrysene ring, a triphenylene ring, an acenaphthene ring, a fluoranthene ring, and a fluorene ring.

　Examples of the aromatic heterocycle of the monovalent group of the aromatic heterocycle include a furan ring, a benzofuran ring, a thiophene ring, a benzothiophene ring, a pyrrole ring, a pyrazole ring, an imidazole ring, a thiazole ring, an isothiazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, an indole ring, a carbazole ring, a pyrroloimidazole ring, a pyrrolopyrazole ring, a pyrrolopyrrole ring, a thienopyrrole ring, a thienothiophene ring, a furopyrrole ring, a furofuran ring, a furothiazole ring, a thienofuran ring, a thienothiazole ring, a benzisoxazole ring, a benzisothiazole ring, a benzimidazole ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinoxaline ring, a phenanthridine ring, a quinazoline ring, an azulene ring, and the like.

-Ra and -Rb are preferably alkyl groups having 1 to 15 carbon atoms which may be branched, or -Ra and -Rb together form a ring having 2 to 15 carbon atoms which may be substituted. Furthermore, -Ra and -Rb are more preferably alkyl groups having 1 to 9 carbon atoms which may be branched, or -Ra and -Rb together form a ring having 2 to 10 carbon atoms; more preferably alkyl groups having 1 to 5 carbon atoms which may be branched, or -Ra and -Rb together form a ring having 2 to 6 carbon atoms; and particularly preferably alkyl groups having 1 to 3 carbon atoms which do not have a branch, or -Ra and -Rb together form a ring having 2 to 6 carbon atoms. The above tends to improve the molecular orientation of compound (1).

-XA is preferably -Ra, -O-Ra, or -C(=O)-O-Ra, more preferably -Ra or -O-Ra, and even more preferably -Ra.

< ^-RA1 and ^-RA2 >
^-RA1 and ^-RA2 each independently represent an alkyl group which may have a substituent. ^-RA1 and ^-RA2 may be joined together to form a ring, but the ^-RA1 and ^-RA2 portions of the ring formed by ^-RA1 and ^-RA2 are formed only by a hydrocarbon chain.

The alkyl group of the alkyl group which may have a substituent of ^-RA1 and ^-RA2 may be linear or branched, and examples thereof include those exemplified as -Ra and -Rb, and the same applies to preferred examples. When the alkyl group has a substituent, a fluorine atom is preferred.

When ^-RA1 and ^-RA2 combine together to form a ring, the ring preferably has 3 to 8 carbon atoms, and more preferably 4 or 5 carbon atoms.
As the substituent which may be possessed by the alkyl groups of ^-RA1 and ^-RA2 or the ring which ^-RA1 and ^-RA2 together form, there may be mentioned those exemplified as the substituents which -Ra and -Rb may have.
From the viewpoint of molecular orientation, ^-RA1 and ^-RA2 are preferably alkyl groups having 1 to 10 carbon atoms, which may have a substituent, more preferably alkyl groups having 1 to 6 carbon atoms, and even more preferably alkyl groups having 1 to 4 carbon atoms.

Specific examples of -N(-RA ¹ )RA ² include dimethylamino, diethylamino, dipropylamino, dibutylamino, ethylmethylamino, methylpropylamino, methylbutylamino, ethylpropylamino, ethylbutyl, azetidinyl, pyrrolidinyl, piperidinyl, azepanyl, and the above group having a fluorine atom. Among these, diethylamino, isopropyl(methyl)amino, ethyl(isopropyl)amino, pyrrolidinyl, piperidinyl, and the above group having a fluorine atom are more preferred. Among the above group having a fluorine atom, di(fluoroethyl)amino, di(fluoropropyl)amino, fluoroethyl(isopropyl)amino, and ethyl(fluoroisopropyl)amino are more preferred.
By satisfying the above, the molecular orientation of compound (1) tends to be good.

<-A ¹ -, -A ² -, -A ³ - and -A ⁴ ->
-A ¹ -, -A ² -, -A ³ - and -A ⁴ - each independently represent a 1,4-phenylene group which may have a substituent.

When the 1,4-phenylene group of -A ¹ -, -A ² -, -A ³ - and -A ⁴ - has a substituent, examples of the substituent include -R ^A , -OH, -O-R ^A , -O-C(═O)-R ^A , -NH ₂ , -NH-R ^A , -N(-R ^B )-R ^A , -C(═O)-R ^A , -C(═O)-O-R ^A , -C(═O)-NH ₂ , -C(═O)-NH-R ^A , -C(═O)-N(-R ^B )-R ^A , -SH, -S-R ^A , trifluoromethyl group, sulfamoyl group, carboxy group, cyano group, nitro group and halogen. Here, -R ^A and -R ^B each independently represent a linear or branched alkyl group having 1 to 15 carbon atoms. The number of carbon atoms in -R ^A and -R ^B is preferably 1 to 12, more preferably 1 to 9, from the viewpoint of improving molecular orientation with the polymerizable liquid crystal compound used in the first invention.

One or more methylene groups contained in the linear or branched alkyl group may be replaced by an ether oxygen atom, a thioether sulfur atom, an aminic nitrogen atom (-NH-, -N( ^Rz )-: here, ^Rz represents a linear or branched alkyl group having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms), a carbonyl group, an ester bond, an amide bond, -CHF-, _-CF2- , -CHCl- or _-CCl2- , or may be substituted by a polymerizable group such as an acryloyloxy group, a methacryloyloxy group or a glycidyloxy group.

Among these, preferred substituents for the 1,4-phenylene group are -R ^A , -O-R ^A , a trifluoromethyl group, and a fluoro group. Examples of -R ^A include n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, and 5,5-dimethyl-3-methylhexyl. The presence of the above-mentioned substituents tends to improve the molecular orientation of the dye of compound (1).

It is preferable that -A ¹ -, -A ² -, -A ³ - and -A ⁴ - are all unsubstituted 1,4-phenylene groups, since the absorption transition moment of compound (1) tends to coincide with the long axis direction of the compound, thereby increasing the dichroic ratio.

(n)
n represents 0, 1, or 2.
n is preferably 0 or 1, and more preferably 1. This tends to improve the molecular orientation of compound (1).
When n is 2, each -A ³ - may be the same or different.

(-N=N-)
In terms of improving the linearity of compound (1), -N=N- in formula (1) is preferably in a trans form.

(Molecular Weight of Compound (1))
The molecular weight of compound (1) is preferably 300 or more, more preferably 350 or more, and even more preferably 380 or more, and is preferably 1500 or less, more preferably 1200 or less, and even more preferably 1000 or less. Specifically, the molecular weight of compound (1) is preferably 300 to 1500, more preferably 350 to 1200, and even more preferably 380 to 1000. When the molecular weight is within the above range, appropriate molecular length and bulkiness are obtained, and therefore the molecular orientation as a dye tends to be good.

(Specific examples of compound (1))
Specific examples of compound (1) include the following compounds, but are not limited to these.

(Method for producing compound (1))
Compound (1) can be produced by combining known chemical reactions such as alkylation reaction, esterification reaction, amidation reaction, etherification reaction, ipso substitution reaction, diazo coupling reaction, and coupling reaction using a metal catalyst.

For example, compound (1) can be synthesized according to the methods described in the Examples below, or in "New Dye Chemistry" (Hosoda Yutaka, December 21, 1973, Gihodo), "General Overview of Synthetic Dyes" (Horiguchi Hiroshi, 1968, Sankyo Publishing), and "Theoretical Manufacturing Dye Chemistry" (Hosoda Yutaka, 1957, Gihodo).

[Composition of the first invention]
The composition of the first invention is a composition containing a compound represented by the following formula (2) (hereinafter, sometimes referred to as "compound (2)") and a polymerizable liquid crystal compound.

The composition of the first invention may be in a solution, liquid crystal, or dispersion state, so long as it does not cause phase separation. The composition for forming an anisotropic dye film is preferably in a solution from the viewpoint of ease of application to a substrate. On the other hand, the solid components remaining after removing the solvent from the composition for forming an anisotropic dye film are preferably in a liquid crystal phase state at any temperature from the viewpoint of alignment on a substrate as described below.

In the present invention, the liquid crystal phase state specifically refers to a liquid crystal state that exhibits both liquid and crystalline properties or intermediate properties, such as a nematic phase, smectic phase, cholesteric phase, or discotic phase, as described on pages 1-16 of "Basics and Applications of Liquid Crystals" (by Shoichi Matsumoto and Ichiro Tsunoda; 1991).

<Compound (2)>
The composition of the first invention contains compound (2) as a dye. It is presumed that by containing compound (2) having the specific structure represented by the above formula (2) as a dye, the dye association state in the anisotropic dye film is optimized, and an anisotropic dye film having good optical properties such as a dichroic ratio when used as a polarizer and high light resistance can be obtained.

The composition of the first invention may contain only one type of compound (2), or may contain two or more types.

(-XB)
-XB represents a monovalent organic group. As -XB, the same groups as -XA in the above formula (1) can be mentioned, and preferred groups are also the same.

( ^-RB1 and ^-RB2 )
Each of ^--RB1 and ^--RB2 independently represents an alkyl group which may have a substituent, and ^--RB1 and ^--RB2 may combine together to form a ring.
Examples of ^--RB1 and ^--RB2 include the same as ^--RA1 and ^--RA2 in the above formula (1), and preferred examples are also the same.

(-B ¹ - and -B ² -)
-B ¹ - and -B ² - each independently represent a 1,4-phenylene group which may have a substituent, and examples of the substituent which the 1,4-phenylene group may have include those exemplified as the substituent which the 1,4-phenylene groups of -A ¹ -, -A ² -, -A ³ - and -A ⁴ - in formula (1) may have, and preferred examples thereof are also the same.
For the same reasons as in compound (1), -B ¹ - and -B ² - are preferably unsubstituted 1,4-phenylene groups.

(-B ³ - and -B ⁴ -)
Each of -B ³ - and -B ⁴ - independently represents a divalent aromatic hydrocarbon ring group which may have a substituent.

Aromatic hydrocarbon rings of divalent groups of aromatic hydrocarbon rings which may have a substituent include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzpyrene ring, a chrysene ring, a triphenylene ring, an acenaphthene ring, a fluoranthene ring, and a fluorene ring.

As the divalent group of the aromatic hydrocarbon ring, the absorption transition moment of compound (2) tends to coincide with the long axis direction of the dye, and the dichroic ratio can be increased, so a divalent group of a benzene ring (phenylene group) or a divalent group of a naphthalene ring (naphthylene group) is preferred, and a divalent group of a benzene ring (phenylene group) is more preferred. In particular, as the divalent group of the aromatic hydrocarbon ring, a 1,4-phenylene group, a 1,4-naphthylene group, or a 2,6-naphthylene group is more preferred, a 1,4-phenylene group is even more preferred, and a 1,4-phenylene group having no substituent is particularly preferred. As a result of the above, the absorption transition moment of compound (2) tends to coincide with the long axis direction of the compound, and the dichroic ratio can be increased.

Examples of the substituent permitted for the divalent group of the aromatic hydrocarbon ring include those exemplified as the substituent which the 1,4-phenylene group of -A ¹ -, -A ² -, -A ³ - and -A ⁴ - may have, and the preferred ones are also the same.

(n)
n represents 0, 1, or 2.
n is preferably 0 or 1, and more preferably 1. In this case, the molecular orientation of compound (2) tends to be good.
When n is 2, each --B ³ -- may be the same or different.

(-N=N-)
In terms of improving the linearity of compound (2), -N=N- in formula (2) is preferably in a trans form.

(Preferred examples of compound (2))
A suitable example of the compound (2) is the above-mentioned compound (1).

(Specific examples of compound (2))
Specific examples of compound (2) include the following compounds in addition to the specific examples of compound (1) described above, but are not limited thereto.

[Composition of the second invention]
The composition of the second invention contains a dye whose maximum absorption wavelength satisfies the following relational expression (11) (hereinafter, may be referred to as "the dye of the second invention") and a polymerizable liquid crystal compound.
The composition of the second invention may contain only one type of the dye of the second invention, or may contain two or more types.
λ _max2 −λ _max1 <0 (11)
(In formula (11), λ _max1 represents the maximum absorption wavelength of the dye in a solvent, and λ _max2 represents the maximum absorption wavelength of the dye in a dye film formed using the composition.)

The composition of the second invention may be in a solution, liquid crystal, or dispersion state, so long as it does not cause phase separation. The composition for forming an anisotropic dye film is preferably in a solution from the viewpoint of ease of application to a substrate. On the other hand, the solid components remaining after removing the solvent from the composition for forming an anisotropic dye film are preferably in a liquid crystal phase state at any temperature from the viewpoint of alignment on a substrate as described below.

<Relationship between maximum absorption wavelength λ _max1 and maximum absorption wavelength λ _max2 of dye and effect>
It is presumed that by containing a dye that satisfies the above-mentioned relational formula (11) in the composition of the second invention, that is, by containing a dye such that the maximum absorption wavelength λ _max1 of the dye in a solvent and the maximum absorption wavelength λ _max2 of the dye in a dye film formed using the composition of the second invention satisfy λ _max2 - λ _max1 < 0, the dye association state in the obtained anisotropic dye film is optimized, and an anisotropic dye film having good optical properties such as the dichroic ratio when used as a polarizer and high light resistance can be obtained.

The dye of the second invention satisfies λ _max2 - λ _max1 < 0, that is, λ _max2 is smaller than λ _max1 , and there is no particular restriction on the difference between λ _max1 and λ _max2 . From the viewpoints of the optical performance such as the dichroic ratio and light fastness of the anisotropic dye film to be formed, it is preferable that the dye of the second invention satisfies the following relational formula (11A).
Furthermore, since optical performance such as the dichroic ratio tends to be better, it is more preferable that λ _max1 and λ _max2 satisfy the following relational expression (11B), and it is even more preferable that they satisfy the following relational expression (11C).
λ _max2 −λ _max1 ≦−1 (11A)
λ _max2 −λ _max1 ≦−10 (11B)
λ _max2 −λ _max1 ≦−20 (11C)

The solvent in which the maximum absorption wavelength λ _max1 of the dye is measured is not particularly limited, and any solvent may be used as long as the dye dissolves to form a homogeneous solution. In the case of a dye that dissolves in chloroform, the maximum absorption wavelength λ _max1 of the dye, i.e., the wavelength λ _max1 at which the absorbance of the dye is maximized, is measured for a solution in which the dye of the second invention is dissolved in chloroform as a solvent to a concentration of about 3 to 30 ppm.
The maximum absorption wavelength λ _max2 of the dye in the dye film is the wavelength λ _max2 at which the orthogonal absorbance of the dye in the dye film is maximized.

In the second invention, the maximum absorption wavelengths λ _max1 and λ _max2 are specifically measured by a spectrophotometer.

The values of the maximum absorption wavelengths λ _max1 and λ _max2 of the dye of the second invention are not particularly limited as long as they satisfy the above-mentioned relational formula (11). However, the maximum absorption wavelength λ _max1 of the dye of the second invention is preferably in the range of 380 to 800 nm, more preferably in the range of 400 to 750 nm, and even more preferably in the range of 410 to 700 nm.
The maximum absorption wavelength λ _max2 of the dye of the second invention is preferably in the range of 350 to 800 nm, more preferably in the range of 380 to 750 nm, and further preferably in the range of 400 to 700 nm.

[Dye of the second invention]
The dye of the second invention is not particularly limited as long as it satisfies the above relational formula (11), preferably the above relational formula (11A), more preferably the above relational formula (11B), and even more preferably the above relational formula (11C), but is preferably an azo dye from the viewpoint of optical performance such as dichroic ratio. Among azo dyes, a compound represented by the following formula (12) (hereinafter sometimes referred to as "compound (12)") tends to have better optical performance such as dichroic ratio, and is therefore preferred.
X ²⁰ (-A ²¹ ) _m1 (-N=N-A ²² ) _n1 -N=N-A ²³ -Y ²⁰ (12)
(In formula (12),
-A ²¹ -, -A ²² -, and -A ²³ - each independently represent a divalent group of an aromatic hydrocarbon ring which may have a substituent, or an aromatic heterocycle which may have a substituent;
-X ²⁰ and -Y ²⁰ each independently represent an arbitrary monovalent substituent;
m1 represents 1 or 2;
n1 represents 0, 1, 2, or 3.
When m1 is 2, -A ²¹ - may be the same or different.
When n1 is 2 or 3, -A ²² - may be the same or different.

Compound (12) is described below.

( ^-A21- , ^-A22- , ^-A23- )
-A ²¹ -, -A ²² - and -A ²³ - each independently represent a divalent group of an aromatic hydrocarbon ring which may have a substituent, or an aromatic heterocycle which may have a substituent.

A divalent group of an aromatic hydrocarbon ring which may have a substituent:
Examples of the aromatic hydrocarbon ring of the divalent group of the aromatic hydrocarbon ring which may have a substituent include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzpyrene ring, a chrysene ring, a triphenylene ring, an acenaphthene ring, a fluoranthene ring, and a fluorene ring.

As the divalent group of the aromatic hydrocarbon ring, the absorption transition moment of compound (12) tends to coincide with the long axis direction of the dye, and the dichroic ratio can be increased, so a divalent group of a benzene ring (phenylene group) or a divalent group of a naphthalene ring (naphthylene group) is preferred, and a divalent group of a benzene ring (phenylene group) is more preferred. In particular, a 1,4-phenylene group, a 1,4-naphthylene group, or a 2,6-naphthylene group is more preferred, a 1,4-phenylene group is even more preferred, and a 1,4-phenylene group having no substituent is particularly preferred. As a result of the above, the absorption transition moment of compound (12) tends to coincide with the long axis direction of the compound, and the dichroic ratio can be increased.

Examples of substituents permitted for the divalent group of the aromatic hydrocarbon ring include -R ^A , -OH, -O-R ^A , -O-C(═O)-R ^A , -NH ₂ , -NH-R ^A , -N(-R ^B )-R ^A , -C(═O)-R ^A , -C(═O)-O-R ^A , -C(═O)-NH ₂ , -C(═O)-NH-R ^A , -C(═O)-N(-R ^B )-R ^A , -SH, -S-R ^A , trifluoromethyl group, sulfamoyl group, carboxy group, cyano group, nitro group, and halogen. Here, -R ^A and -R ^B each independently represent a straight-chain or branched alkyl group having 1 to 15 carbon atoms. The number of carbon atoms in -R ^A and -R ^B is preferably 1 or more and 12 or less, and more preferably 1 or more and 9 or less, from the viewpoint of improving molecular alignment with the polymerizable liquid crystal compound used in the present invention.

Among these, preferred examples of the substituent permitted for the divalent group of the aromatic hydrocarbon ring are -R ^A , -O-R ^A , a trifluoromethyl group, and a fluoro group. Examples of -R ^A include n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, and 5,5-dimethyl-3-methylhexyl. The presence of the above-mentioned substituents tends to improve the molecular orientation of the dye of compound (2).

A divalent group of an aromatic heterocycle which may have a substituent:
Examples of the aromatic heterocycle of the divalent group of the aromatic heterocycle which may have a substituent include a furan ring, a benzofuran ring, a thiophene ring, a benzothiophene ring, a pyrrole ring, a pyrazole ring, an imidazole ring, a thiazole ring, an isothiazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, an indole ring, a carbazole ring, a pyrroloimidazole ring, a pyrrolopyrazole ring, a pyrrolopyrrole ring, a thienopyrrole ring, a thienothiophene ring, a furopyrrole ring, a furofuran ring, a furothiazole ring, a thienofuran ring, a thienothiazole ring, a benzisoxazole ring, a benzisothiazole ring, a benzimidazole ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinoxaline ring, a phenanthridine ring, a quinazoline ring, and an azulene ring.

Permissible substituents for the divalent group of the aromatic heterocycle include the same as those that may be possessed by the divalent group of the aromatic hydrocarbon ring, and the preferred substituents are also the same.

(Preferred embodiments of -A ²¹ -, -A ²² -, -A ²³ -)
Of -A ²¹ -, -A ²² -, and -A ²³ -, from the viewpoints of optical performance such as dichroic ratio and the optimal dye association state, -A ²¹ - and -A ²³ - are preferably each independently a divalent group of an aromatic hydrocarbon ring which may have a substituent, more preferably each independently a phenylene group which may have a substituent, particularly preferably a 1,4-phenylene group which may have a substituent, and particularly preferably an unsubstituted 1,4-phenylene group.

With respect to -A ²² -, from the viewpoint of optical performance such as dichroic ratio, it is preferable that it is a divalent group of an aromatic hydrocarbon ring which may have a substituent, it is more preferable that it is a phenylene group which may have a substituent, it is particularly preferable that it is a 1,4-phenylene group which may have a substituent, and it is particularly preferable that it is a 1,4-phenylene group which has no substituent.

(-X ²⁰ , -Y ²⁰ )
Each of -X ²⁰ and -Y ²⁰ independently represents any monovalent substituent.
Examples of the monovalent substituent in -X ²⁰ and -Y ²⁰ include a hydroxy group, an amino group, a cyano group, a carbamoyl group, a nitro group, a halogen atom, -R ^x , -O-R ^x , -NH-R ^x , -N(-R ^y )-R ^x , -C(=O)-R ^x , -C(=O)-O-R ^x , -C(=O)-NH-R ^x , -C(=O)-N(-R ^y )-R ^x , -O-C(=O)-R ^x , -NH-C(=O)-R ^x , and -N(-R ^y )-C(=O)-R ^x . -R ^x and -R ^y each independently represent an alkyl group, a cycloalkyl group, or an aryl group which may have a branch, and these may have a substituent. The alkyl group preferably has 1 to 15 carbon atoms, the cycloalkyl group preferably has 5 to 14 ring atoms, and the aryl group preferably has 5 to 14 ring atoms.
--R ^x and --R ^y may join together to form a ring preferably having 2 to 15 carbon atoms, more preferably 2 to 10 carbon atoms.

From the viewpoint of improving molecular alignment with the polymerizable liquid crystal compound used in the second invention, it is preferable that the monovalent substituents in -X ²⁰ and -Y ²⁰ do not have a polymerizable group as described below, while from the viewpoint of improving the mechanical strength of the anisotropic dye film, it is preferable that the monovalent substituents in -X ²⁰ and -Y ²⁰ have a polymerizable group as described below.

An alkyl group having 1 to 15 carbon atoms, which may be branched, preferably has 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms. A cycloalkyl group having 5 to 14 ring atoms preferably has 5 to 10 ring atoms, more preferably 5 to 6 ring atoms, and even more preferably 6 ring atoms. An aryl group having 5 to 14 ring atoms preferably has 5 to 10 ring atoms, more preferably 5 to 6 ring atoms, and even more preferably 6 ring atoms. The above tends to result in good optical performance such as dichroic ratio and optimal dye association state.

An alkyl group having 1 to 15 carbon atoms, which may be branched, a cycloalkyl group having 5 to 14 atoms constituting a ring, and an aryl group having 5 to 14 atoms constituting a ring may each have a substituent.

Furthermore, one or more methylene groups contained in an alkyl group having 1 to 15 carbon atoms which may have a branch, a cycloalkyl group having 5 to 14 ring atoms, or a ring formed by combining -R ^x and -R ^y may have a structure in which they are replaced (displaced) by -O-, -S-, -NH-, -N(R ^z )-, -C(═O)-, -C(═O)-O-, -C(═O)-NH-, -CHF-, -CF ₂ -, -CHCl-, or -CCl ₂ -, or may have a structure in which they are replaced by a polymerizable group such as an acryloyloxy group, a methacryloyloxy group, or a glycidyloxy group. Here, R ^z represents a straight-chain or branched alkyl group having 1 to 6 carbon atoms.

Examples of the substituents permitted for the branched alkyl group having 1 to 15 carbon atoms in -R ^x and -R ^y include -OH, -O-R ^f , -O-C(=O)-R ^f , -NH ₂ , -NH-R ^f , -N(-R ^g )-R ^f , -C(=O)-R ^f , -C(=O)-O-R ^f , -C(=O)-NH ₂ , -C(=O)-NH-R ^f , -C(=O)-N(-R ^g )-R ^f , -SH, -S-R ^f , a sulfamoyl group, a carboxy group, a cyano group, a nitro group, a halogen, etc. Here, -R ^f and -R ^g each independently represent a straight-chain or branched alkyl group having 1 to 15 carbon atoms, preferably 1 to 10 carbon atoms.
One or more methylene groups contained in the linear or branched alkyl group having 1 to 15 carbon atoms may be displaced by -O-, -S-, -NH-, -N(R ^h )-, -C(═O)-, -C(═O)-O-, -C(═O)-NH-, -CHF-, -CF ₂ -, -CHCl-, or -CCl ₂ -, or may be replaced by a polymerizable group such as an acryloyloxy group, a methacryloyloxy group, or a glycidyloxy group. R ^h represents a linear or branched alkyl group having 1 to 6 carbon atoms.
Among these, the substituent permitted for the branched alkyl group having 1 to 15 carbon atoms in -R ^x and -R ^y is preferably -O-R ^f , and examples thereof include methoxy, ethoxy, n-propoxy, n-butoxy, n-pentoxy, n-hexoxy, n-heptoxy, n-octoxy, acryloyloxy, methacryloyloxy, and glycidyloxy.

Examples of the substituents permitted for the cycloalkyl group or aryl group having 5 to 14 ring atoms in -R ^x and -R ^y include -R ⁱ , -OH, -O-R ⁱ , -O-C(=O)-R ⁱ , -NH ₂ , -NH-R ⁱ , -N(-R ^j )-R ⁱ , -C(=O)-R ⁱ , -C(=O)-O-R ⁱ , -C(=O)-NH ₂ , -C(=O)-NH-R ⁱ , -C(=O)-N(-R ^j )-R ⁱ , -SH, -S-R ⁱ , trifluoromethyl group, sulfamoyl group, carboxy group, cyano group, nitro group, and halogen. -R ⁱ and -R ^j each independently represent a straight-chain or branched alkyl group having 1 to 10 carbon atoms, preferably 1 to 5 carbon atoms.

Among these, preferred substituents for the cycloalkyl group or aryl group having 5 to 14 ring-constituting atoms in -R ^x and -R ^y are -R ⁱ and -O-R ⁱ , and examples thereof include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, methoxy, ethoxy, n-propoxy, n-butoxy, n-pentoxy, n-hexoxy, n-heptoxy, n-octoxy, 2-ethylhexyloxy, 5,5-dimethyl-3-methylhexyloxy, and the like.

Examples of the cycloalkane ring of the cycloalkyl group having 5 to 14 ring-constituting atoms of -R ^x and -R ^y include a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, a cyclooctane ring, a cyclohexene ring, a norbornane ring, a bornane ring, an adamantane ring, a tetrahydronaphthalene ring, and a bicyclo[2.2.2]octane ring.

Examples of the aryl group having 5 to 14 ring-constituting atoms of -R ^x and -R ^y include the monovalent groups of the rings exemplified as the aromatic heterocycle and aromatic hydrocarbon ring in -A ²¹ -, -A ²² -, and -A ²³ -.

As -R ^x and -R ^y , it is preferable that they are an alkyl group having 1 to 15 carbon atoms which may have a branch, or -R ^x and -R ^y together form a ring having 2 to 15 carbon atoms which may have a substituent. Furthermore, it is more preferable that they are an alkyl group having 1 to 6 carbon atoms which may have a branch, or -R ^x and -R ^y together form a ring having 2 to 10 carbon atoms; it is more preferable that they are an alkyl group having 1 to 3 carbon atoms which may have a branch, or -R ^x and -R ^y together form a ring having 2 to 6 carbon atoms; it is particularly preferable that they are an alkyl group having 1 to 3 carbon atoms which does not have a branch, or -R ^x and -R ^y together form a ring having 2 to 6 carbon atoms. By being as described above, the molecular orientation of the compound (12) tends to be good.

Of the monovalent substituents in -X ²⁰ and -Y ²⁰ , -X ²⁰ is preferably -R ^x , -O-R ^x , -O-C(=O)-R ^x , -C(=O)-O-R ^x , -N(-R ^y )-R ^x or -NH-R ^x , more preferably -R ^x , -O-R ^x , -O-C(=O)-R ^x or -C(=O)-O-R ^x , and particularly preferably -R ^x or -O-R ^x . Specifically, -R ^x is preferably a cycloalkyl group having 5 to 8 carbon atoms constituting the ring, which has no substituent or has an alkyl group having 1 to 10 carbon atoms as a substituent at the p-position, more preferably a cyclohexyl group having no substituent or has an alkyl group having 1 to 10 carbon atoms as a substituent at the p-position, and even more preferably a cyclohexyl group having an alkyl group having 3 to 6 carbon atoms as a substituent at the p-position. As -O-R ^x , -R ^x is preferably an alkyl group having 3 to 12 carbon atoms which may have a branch, and more preferably -R ^x is an alkyl group having 3 to 10 carbon atoms which may have a branch.
As -Y ²⁰ , -R ^x , -O-R ^x , -O-C(═O)-R ^x , -C(═O)-O-R ^x , and -N(-R ^y )-R ^x are preferable, -O-R ^x , -O-C(═O)-R ^x , and -N(-R ^y )-R ^x are more preferable, -O-R ^x , -N(-R ^y )-R ^x , and -NH-R ^x are even more preferable, and a group represented by the following formula (12a) is particularly preferable.
-N-(R ^y )-R ^x (12a)
(In formula (12a), -R ^x and -R ^y each independently represent an alkyl group or an aryl group which may have a branch, and the alkyl group or aryl group may have a substituent. -R ^x and -R ^y may together form a ring having 2 to 15 carbon atoms together with N, and the ring may have a substituent.)

Specific examples of the group represented by formula (12a) include preferred dimethylamino, diethylamino, di-n-propylamino, ethylmethylamino, methylpropylamino, ethylpropylamino, methylbutylamino, ethylbutylamino, azetidinyl, pyrrolidinyl, piperidinyl, azepanyl, morpholinyl, piperazinyl, and thiomorpholinyl groups, with diethylamino, pyrrolidinyl, and piperidinyl groups being more preferred.
In the above case, the absorption transition moment of compound (12) coincides with the long axis direction of the compound, and therefore the dichroism tends to be good.

When high solubility of the dye is required, -R ^x and/or -R ^y in formula ( ^12a ⁾ are preferably a branched alkyl group, more preferably an isopropyl group or an isobutyl group.
In the formula (12a), -R ^x and -R ^y preferably have a substituent when it is necessary to adjust the absorption wavelength of the dye, and as the substituent, -OH, -O-R ^f , -O-C(═O)-R ^f , -C(═O)-R ^f , -C(═O)-O-R ^f , or a halogen atom is more preferable, and a fluorine atom is even more preferable. Here, -R ^f represents a linear or branched alkyl group having 1 to 15 carbon atoms, preferably 1 to 10 carbon atoms.

(m1)
m1 represents 1 or 2.
m1 is preferably 2. This tends to result in an optimal dye association state.
When m1 is 2, each -A ²¹ - may be the same or different, but is preferably the same since this tends to result in an optimal dye association state.

(n1)
n1 represents 0, 1, 2, or 3.
n1 is preferably 1 or 2 since this tends to result in an optimal dye association state, and more preferably 1 since this tends to result in better molecular orientation of compound (12).
When n1 is 2 or 3, each -A ²² - may be the same or different, but is preferably the same since this tends to result in an optimal dye association state.

The sum of m1 and n1 is not particularly limited as long as m1 and n1 are within the above range, but is preferably 2 or 3, and more preferably 3. This tends to improve the molecular orientation of compound (12).

(-N=N-)
In terms of improving the linearity of compound (12), -N=N- in formula (12) is preferably a trans type.

(Specific examples of compound (12))
Specific examples of compound (12) include the following compounds, but are not limited thereto.

[Dye in the composition of the present invention]
The composition of the first invention contains compound (2). The composition of the first invention may contain a dye other than compound (2). Examples of the dye other than compound (2) contained in the composition of the first invention include azo dyes other than compound (2), quinone dyes (including naphthoquinone dyes, anthraquinone dyes, etc.), stilbene dyes, cyanine dyes, phthalocyanine dyes, indigo dyes, and condensed polycyclic dyes (including perylene dyes, oxazine dyes, acridine dyes, etc.).
The composition of the first invention may contain only one type of dye other than compound (2) alone, or may contain two or more types in any combination and ratio.

The composition of the second invention preferably contains compound (12) as the dye of the second invention. The composition of the second invention may contain a dye other than the dye of the second invention. Examples of the dye other than the dye of the second invention contained in the composition of the second invention that do not satisfy the above relational formula (11) include azo dyes, quinone dyes (including naphthoquinone dyes, anthraquinone dyes, etc.), stilbene dyes, cyanine dyes, phthalocyanine dyes, indigo dyes, and condensed polycyclic dyes (including perylene dyes, oxazine dyes, acridine dyes, etc.).

The composition of the present invention, i.e., the composition of the first invention and the composition of the second invention, preferably contains a dye other than compound (2) or the dye of the second invention, whose wavelength showing a maximum value in the absorption curve in the wavelength range of 350 nm to 800 nm is 5 nm or more different from the wavelength showing a maximum value in the absorption curve in the wavelength range of 350 nm to 800 nm of compound (2) or the dye of the second invention contained in the composition, and more preferably contains a compound whose wavelength showing a maximum value in the absorption curve in the wavelength range of 350 nm to 800 nm is 10 nm or more different from the wavelength showing a maximum value in the absorption curve in the wavelength range of 350 nm to 800 nm of compound (2) or the dye of the second invention contained in the composition. As described above, when the composition of the present invention is used to form an anisotropic dye film into a polarizing element such as a display, it is preferable in that it expresses polarization characteristics in a wide range of the visible region.

(Molecular weight of dye)
The molecular weight of the dye contained in the composition of the present invention (when two or more dyes are used in combination, the molecular weight of each dye) is preferably 300 or more, more preferably 350 or more, and even more preferably 380 or more, and is preferably 1500 or less, more preferably 1200 or less, and even more preferably 1000 or less. Specifically, the molecular weight of the dye contained in the composition of the present invention is preferably 300 to 1500, more preferably 350 to 1200, and even more preferably 380 to 1000. By being in the above range, the molecular length and bulkiness are appropriate, and therefore the molecular orientation of the dye tends to be good. The molecular weight of the dye is the sum of the atomic weights contained in the dye molecule.

(Pigment content)
The content of the dye in the composition of the present invention (when two or more dyes are used in combination, the total content of each dye) is, for example, preferably 0.01 parts by mass or more, more preferably 0.05 parts by mass or more, and preferably 30 parts by mass or less, more preferably 10 parts by mass or less, relative to the solid content (100 parts by mass) of the composition. Specifically, the content of the dye in the composition is, for example, preferably 0.01 to 30 parts by mass, more preferably 0.05 to 10 parts by mass, relative to the solid content (100 parts by mass) of the composition.

If the content of the dye is within the above range, the polymerizable liquid crystal compound contained in the composition of the present invention tends to be polymerized without disturbing the alignment of the liquid crystal compound contained in the composition of the present invention. If the content of the dye is equal to or greater than the above lower limit, sufficient light absorption and sufficient polarization performance tend to be obtained. If the content of the dye is equal to or less than the above upper limit, inhibition of the alignment of the liquid crystal molecules tends to be suppressed.

Here, the solids content of the composition corresponds to the sum of all components in the composition other than the solvent.

The composition of the present invention may contain, as an essential component, compound (2) or the dye of the second invention as a dye, and may also contain the above-mentioned other dyes together with compound (2) or the dye of the second invention.
When the composition of the present invention contains another dye, from the viewpoint of more effectively obtaining the effects of the present invention by using compound (2) or the dye of the second invention, the proportion of compound (2) or the dye of the second invention in 100% by mass of the total amount of dyes in the composition of the present invention is preferably 5% by mass or more, more preferably 10% by mass or more, and particularly preferably 15 to 100% by mass.

(Method of producing dye)
Compound (2) contained in the composition of the present invention and dyes such as the dye of the second invention can be produced by combining known chemical reactions such as an alkylation reaction, an esterification reaction, an amidation reaction, an etherification reaction, an ipso substitution reaction, a diazo coupling reaction, and a coupling reaction using a metal catalyst.

For example, compound (2), the dye of the second invention, can be synthesized according to the method described in the Examples below, or in "New Dye Chemistry" (Hosoda Yutaka, December 21, 1973, Gihodo), "General Synthetic Dyes" (Horiguchi Hiroshi, 1968, Sankyo Publishing), and "Theoretical Manufacturing Dye Chemistry" (Hosoda Yutaka, 1957, Gihodo).

[Polymerizable Liquid Crystal Compound]
In the present invention, the liquid crystal compound refers to a substance that exhibits a liquid crystal state, and specifically refers to a compound that does not directly transition from a crystal to a liquid state but becomes a liquid state via an intermediate state that exhibits properties of both a crystal and a liquid, as described on pages 1 to 28 of "Liquid Crystal Handbook" (Maruzen Co., Ltd., published on October 30, 2000).

The polymerizable liquid crystal compound contained in the composition of the present invention is a liquid crystal compound having a polymerizable group, which will be described later.

In the polymerizable liquid crystal compound, the polymerizable group can be located at any position in the liquid crystal compound molecule. In the polymerizable liquid crystal compound, the polymerizable group is preferably substituted at the terminal of the liquid crystal compound molecule from the viewpoint of ease of polymerization.
In the polymerizable liquid crystal compound, one or more polymerizable groups may be present in the liquid crystal compound molecule. When two or more polymerizable groups are present, it is preferable that they are present at both ends of the liquid crystal compound molecule from the viewpoint of ease of polymerization.

The polymerizable liquid crystal compound is preferably a compound having a carbon-carbon triple bond in the liquid crystal compound molecule. In a compound having a carbon-carbon triple bond, the carbon-carbon triple bond is capable of rotational motion while also being able to become the core of the liquid crystal molecule, and the molecular mobility is high, and there is strong intermolecular interaction between the liquid crystal molecules and with compounds having a π-conjugated system such as dye molecules, which tends to result in high molecular orientation.

The polymerizable liquid crystal compound contained in the composition of the present invention is not particularly limited, and any liquid crystal compound having a polymerizable group can be used.

For example, the polymerizable liquid crystal compound contained in the composition of the present invention may be a compound represented by the following formula (3) (hereinafter, sometimes referred to as "polymerizable liquid crystal compound (3)").

Q ¹ -R ¹ -A ¹¹ -Y ¹ -A ¹² -(Y ² -A ¹³ ) _k -R ² -Q ² (3)

(In formula (3),
^-Q1 represents a hydrogen atom or a polymerizable group;
^-Q2 represents a polymerizable group;
-R ¹ - and -R ² - each independently represent a chain organic group;
-A ¹¹ - and -A ¹³ - each independently represent a partial structure represented by the following formula (4), a divalent organic group, or a single bond:
-A ¹² - represents a partial structure represented by the following formula (4) or a divalent organic group:
-Y ¹ - and -Y ² - each independently represent a single bond, -C(=O)O-, -OC(=O)-, -C(=S)O-, -OC(=S)-, -C(=O)S-, -SC(=O)-, -CH ₂ CH ₂ -, -CH=CH-, -C≡C-, -C(=O)NH-, -NHC(=O)-, -CH ₂ O-, -OCH ₂ -, -CH ₂ S-, or -SCH ₂ -;
One of -A ¹¹ - and -A ¹³ - is a partial structure represented by the following formula (4) or a divalent organic group:
k is 1 or 2.
When k is 2, two -Y ² -A ¹³ - may be the same or different.

-C ^y -X ² -C≡C-X ¹ - (4)
(In formula (4),
-C ^y - represents a hydrocarbon ring group or a heterocyclic group;
-X ¹ - represents -C(=O)O-, -OC(=O)-, -C(=S)O-, -OC(=S)-, -C(=O)S-, -SC(=O)-, -CH ₂ CH ₂ -, -CH=CH-, -C(=O)NH-, -NHC(=O)-, -CH ₂ O-, -OCH ₂ -, -CH ₂ S-, or -SCH ₂ -;
-X ² - represents a single bond, -C(=O)O-, -OC(=O)-, -C(=S)O-, -OC(=S)-, -C(=O)S-, -SC(=O)-, -CH ₂ CH ₂ -, -CH=CH-, -C(=O)NH-, -NHC(=O)-, -CH ₂ O-, -OCH ₂ -, -CH ₂ S-, or -SCH ₂ -.

When -A ¹¹ - is a partial structure represented by formula (4), formula (3) may be the following formula (3A) or the following formula (3B).
Q ¹ -R ¹ -C ^y -X ² -C≡C-X ¹ -Y ¹ -A ¹² -(Y ² -A ¹³ ) _k -R ² -Q ² (3A)
Q ¹ -R ¹ -X ¹ -C≡C-X ² -C ^y -Y ¹ -A ¹² -(Y ² -A ¹³ ) _k -R ² -Q ² (3B)

Furthermore, when -A ¹² - is a partial structure represented by formula (4), formula (3) may be the following formula (3C) or the following formula (3D).
Q ¹ -R ¹ -A ¹¹ -Y ¹ -C ^y -X ² -C≡C-X ¹ -(Y ² -A ¹³ ) _k -R ² -Q ² (3C)
Q ¹ -R ¹ -A ¹¹ -Y ¹ -X ¹ -C≡C-X ² -C ^y -(Y ² -A ¹³ ) _k -R ² -Q ² (3D)

Furthermore, when -A ¹³ - is a partial structure represented by formula (4), formula (3) may be the following formula (3E) or the following formula (3F).
Q ¹ -R ¹ -A ¹¹ -Y ¹ -A ¹² -(Y ² -C ^y -X ² -C≡C-X ¹ ) _k -R ² -Q ² (3E)
Q ¹ -R ¹ -A ¹¹ -Y ¹ -A ¹² -(Y ² -X ¹ -C≡C-X ² -C ^y ) _k -R ² -Q ² (3F)

Similarly, when two or more of -A ¹¹ -, -A ¹² - and -A ¹³ - are partial structures represented by formula (4), the orientation of the partial structures represented by formula (4) may be inverted, each independently.

As described above, -A ¹¹ -, -A ¹² - and -A ¹³ - are each independently a partial structure or a divalent organic group represented by formula (4). In addition, -A ¹¹ - and -A ¹³ - may be a single bond, but -A ¹¹ - and -A ¹³ - are not both single bonds.

(-C ^y -)
The hydrocarbon ring group in -C ^y - includes an aromatic hydrocarbon ring group and a non-aromatic hydrocarbon ring group.
The aromatic hydrocarbon ring group includes an unlinked aromatic hydrocarbon ring group and a linked aromatic hydrocarbon ring group.

The non-linked aromatic hydrocarbon ring group is a divalent group of a monocyclic or condensed aromatic hydrocarbon ring, and preferably has 6 to 20 carbon atoms, because the appropriate core size provides good molecular orientation. The non-linked aromatic hydrocarbon ring group more preferably has 6 to 15 carbon atoms. Examples of aromatic hydrocarbon rings include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzpyrene ring, a chrysene ring, a triphenylene ring, an acenaphthene ring, a fluoranthene ring, and a fluorene ring.

The linked aromatic hydrocarbon ring group is a divalent group in which a plurality of monocyclic or condensed aromatic hydrocarbon rings are bonded by single bonds and have a bond on an atom constituting the ring. The number of carbon atoms in the monocyclic or condensed ring is preferably 6 to 20 because the molecular orientation is good due to the appropriate core size. The number of carbon atoms in the monocyclic or condensed ring is more preferably 6 to 15. Examples of the linked aromatic hydrocarbon ring group include a divalent group in which a first monocyclic or condensed aromatic hydrocarbon ring having 6 to 20 carbon atoms is bonded by a single bond to a second monocyclic or condensed aromatic hydrocarbon ring having 6 to 20 carbon atoms, which has a first bond on an atom constituting the ring of the first monocyclic or condensed aromatic hydrocarbon ring having 6 to 20 carbon atoms, and a second bond on an atom constituting the ring of the second monocyclic or condensed aromatic hydrocarbon ring having 6 to 20 carbon atoms. Specific examples of the linked aromatic hydrocarbon ring group include a biphenyl-4,4'-diyl group.

As the aromatic hydrocarbon ring group, a non-linked aromatic hydrocarbon ring group is preferable because it optimizes the intermolecular interaction acting between liquid crystal compounds, thereby improving the molecular alignment.
Of these, the aromatic hydrocarbon ring group is preferably a divalent group of a benzene ring or a divalent group of a naphthalene ring, and more preferably a divalent group of a benzene ring (phenylene group). As the phenylene group, a 1,4-phenylene group is preferable. When -C ^y - is one of these groups, the linearity of the liquid crystal molecules is increased, and the effect of improving molecular alignment tends to be obtained.

Non-aromatic hydrocarbon ring groups include unlinked non-aromatic hydrocarbon ring groups and linked non-aromatic hydrocarbon ring groups.

The non-linked non-aromatic hydrocarbon ring group is a divalent group of a monocyclic or condensed non-aromatic hydrocarbon ring, and preferably has 3 to 20 carbon atoms because the appropriate core size provides good molecular orientation. The non-linked non-aromatic hydrocarbon ring group more preferably has 3 to 15 carbon atoms. Examples of non-aromatic hydrocarbon rings include a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, a cyclooctane ring, a cyclohexene ring, a norbornane ring, a bornane ring, an adamantane ring, a tetrahydronaphthalene ring, and a bicyclo[2.2.2]octane ring.

　The non-linked non-aromatic hydrocarbon ring group includes an alicyclic hydrocarbon ring group that does not have an unsaturated bond between the atoms that constitute the ring of the non-aromatic hydrocarbon ring, and an unsaturated non-aromatic hydrocarbon ring group that has an unsaturated bond between the atoms that constitute the ring of the non-aromatic hydrocarbon ring. From the viewpoint of productivity, the non-linked non-aromatic hydrocarbon ring group is preferably an alicyclic hydrocarbon ring group.

The linked non-aromatic hydrocarbon ring group is a divalent group in which a plurality of monocyclic or condensed non-aromatic hydrocarbon rings are bonded together with single bonds and has a bond on an atom constituting the ring; or a divalent group in which one or more rings selected from the group consisting of monocyclic aromatic hydrocarbon rings, condensed aromatic hydrocarbon rings, monocyclic non-aromatic hydrocarbon rings, and condensed non-aromatic hydrocarbon rings are bonded together with a monocyclic or condensed non-aromatic hydrocarbon ring with a single bond and has a bond on an atom constituting the ring.
The number of carbon atoms in the single ring or condensed ring is preferably 3 to 20 because an appropriate core size provides good molecular orientation.

Examples of the linked non-aromatic hydrocarbon ring group include a divalent group in which a first monocyclic or condensed non-aromatic hydrocarbon ring having 3 to 20 carbon atoms is bonded to a second monocyclic or condensed non-aromatic hydrocarbon ring having 3 to 20 carbon atoms by a single bond, the divalent group having a first bond on an atom constituting the first monocyclic or condensed non-aromatic hydrocarbon ring having 3 to 20 carbon atoms, and a second bond on an atom constituting the second monocyclic or condensed non-aromatic hydrocarbon ring having 3 to 20 carbon atoms. Further examples include a divalent group in which a monocyclic or condensed aromatic hydrocarbon ring having 3 to 20 carbon atoms is bonded to a monocyclic or condensed non-aromatic hydrocarbon ring having 3 to 20 carbon atoms by a single bond, the divalent group having a first bond on an atom constituting the monocyclic or condensed aromatic hydrocarbon ring having 3 to 20 carbon atoms, and a second bond on an atom constituting the monocyclic or condensed non-aromatic hydrocarbon ring having 3 to 20 carbon atoms.

Specific examples of linking non-aromatic hydrocarbon ring groups include bis(cyclohexane)-4,4'-diyl and 1-cyclohexylbenzene-4,4'-diyl groups.

As the non-aromatic hydrocarbon ring group, a non-linked non-aromatic hydrocarbon ring group is preferred because it optimizes the intermolecular interactions that act between liquid crystal compounds, thereby improving molecular orientation.

As the non-linked non-aromatic hydrocarbon ring group, a divalent group of cyclohexane (cyclohexanediyl group) is preferable. As the cyclohexanediyl group, a cyclohexane-1,4-diyl group is preferable. When -C ^y - is one of these groups, the linearity of the liquid crystal molecules is increased, and the effect of improving molecular alignment tends to be obtained.

The heterocyclic group in -C ^y - includes an aromatic heterocyclic group and a non-aromatic heterocyclic group.

Aromatic heterocyclic groups include unlinked aromatic heterocyclic groups and linked aromatic heterocyclic groups.

The non-linked aromatic heterocyclic group is a divalent group of a monocyclic or condensed aromatic heterocyclic ring, and preferably has 4 to 20 carbon atoms because the appropriate core size provides good molecular orientation. The non-linked aromatic heterocyclic group more preferably has 4 to 15 carbon atoms.

Aromatic heterocycles include furan ring, benzofuran ring, thiophene ring, benzothiophene ring, pyrrole ring, pyrazole ring, imidazole ring, thiazole ring, isothiazole ring, oxadiazole ring, thiadiazole ring, triazole ring, indole ring, carbazole ring, pyrroloimidazole ring, pyrrolopyrazole ring, pyrrolopyrrole ring, thienopyrrole ring, thienothiophene ring, furopyrrole ring, furofuran ring, thienofuran ring, thienothiazole ring, benzoisoxazole ring, benzoisothiazole ring, benzimidazole ring, pyridine ring, pyrazine ring, pyridazine ring, pyrimidine ring, triazine ring, quinoline ring, isoquinoline ring, cinnoline ring, quinoxaline ring, phenanthridine ring, quinazoline ring, quinazolinone ring, azulene ring, etc.

The linked aromatic heterocyclic group is a divalent group in which multiple monocyclic or condensed aromatic heterocyclic rings are bonded with single bonds and have bonds on the atoms that make up the ring. The number of carbon atoms in the monocyclic or condensed ring is preferably 4 to 20, because the appropriate core size provides good molecular orientation. The number of carbon atoms in the linked aromatic heterocyclic group is more preferably 4 to 15.

Examples of linked aromatic heterocyclic groups include divalent groups in which a first monocyclic or condensed aromatic heterocyclic ring having 4 to 20 carbon atoms is bonded to a second monocyclic or condensed aromatic heterocyclic ring having 4 to 20 carbon atoms by a single bond, the divalent group having a first bond on an atom constituting the ring of the first monocyclic or condensed aromatic heterocyclic ring having 4 to 20 carbon atoms, and a second bond on an atom constituting the ring of the second monocyclic or condensed aromatic heterocyclic ring having 4 to 20 carbon atoms.

Non-aromatic heterocyclic groups include unlinked non-aromatic heterocyclic groups and linked non-aromatic heterocyclic groups.

The non-linked non-aromatic heterocyclic group is a divalent group of a monocyclic or condensed non-aromatic heterocyclic ring, and preferably has 4 to 20 carbon atoms because the appropriate core size provides good molecular orientation. The non-linked non-aromatic heterocyclic group more preferably has 4 to 15 carbon atoms.

Examples of non-aromatic heterocycles that are divalent groups of monocyclic or condensed non-aromatic heterocycles having 4 to 20 carbon atoms include a tetrahydrofuran ring, a tetrahydropyran ring, a dioxane ring, a tetrahydrothiophene ring, a tetrahydrothiopyran ring, a pyrrolidine ring, a piperidine ring, a dihydropyridine ring, a piperazine ring, a tetrahydrothiazole ring, a tetrahydrooxazole ring, an octahydroquinoline ring, a tetrahydroquinoline ring, an octahydroquinazoline ring, a tetrahydroquinazoline ring, a tetrahydroimidazole ring, a tetrahydrobenzimidazole ring, and a quinuclidine ring.

　A linked non-aromatic heterocyclic group is a divalent group in which multiple monocyclic or condensed non-aromatic heterocyclic rings are bonded with single bonds and have bonds on the atoms that make up the ring. The number of carbon atoms in the monocyclic or condensed ring is preferably 4 to 20, because the appropriate core size provides good molecular orientation. The number of carbon atoms in the linked non-aromatic heterocyclic group is more preferably 4 to 15.

Examples of linked aromatic heterocyclic groups include divalent groups in which a first monocyclic or condensed non-aromatic heterocyclic ring having 4 to 20 carbon atoms is bonded to a second monocyclic or condensed non-aromatic heterocyclic ring having 4 to 20 carbon atoms by a single bond, the divalent group having a first bond on an atom constituting the ring of the first monocyclic or condensed non-aromatic heterocyclic ring having 4 to 20 carbon atoms, and a second bond on an atom constituting the ring of the second monocyclic or condensed non-aromatic heterocyclic ring having 4 to 20 carbon atoms.

The aromatic hydrocarbon ring group, non-aromatic hydrocarbon ring group, aromatic heterocyclic group and non-aromatic heterocyclic group in -C ^y - may each be substituted with one or more groups selected from the group consisting of -R ^k , -OH, -O-R ^k , -O-C(═O)-R ^k , -NH ₂ , -NH-R ^k , -N(R ^k' )-R ^k , -C(═O)-R ^k , -C(═O)-O-R ^k , -C(═O)-NH ₂ , -C(═O)-NH-R ^k , -C(═O)-N(R ^k' )-R ^k , -SH, -S-R ^k , trifluoromethyl group, sulfamoyl group, carboxy group, sulfo group, cyano group, nitro group, and halogen. Each of --R ^k and --R ^k' independently represents a linear or branched alkyl group having 1 to 6 carbon atoms.

The aromatic hydrocarbon ring group, non-aromatic hydrocarbon ring group, aromatic heterocyclic group and non-aromatic heterocyclic group in -C ^y - are each preferably independently unsubstituted or substituted with a methyl group, a methoxy group, a fluorine atom, a chlorine atom or a bromine atom, and more preferably unsubstituted, in terms of high linearity of the molecular structure, and ease of association of the polymerizable liquid crystal compounds (3) with each other to exhibit a liquid crystal state.

The substituents possessed by the aromatic hydrocarbon ring group, non-aromatic hydrocarbon ring group, aromatic heterocyclic group and non-aromatic heterocyclic group in -C ^y - may be the same or different. In addition, the aromatic hydrocarbon ring group, non-aromatic hydrocarbon ring group, aromatic heterocyclic group and non-aromatic heterocyclic group may be entirely substituted, entirely unsubstituted, or partly substituted and partly unsubstituted.

As -C ^y -, a hydrocarbon ring group is preferable, and a phenylene group or a cyclohexanediyl group is more preferable, because the molecular alignment of the polymerizable liquid crystal compound (3) is improved. As -C ^y -, a 1,4-phenylene group or a cyclohexane-1,4-diyl group is further preferable, and a 1,4-phenylene group is particularly preferable, because the linearity of the molecular structure of the polymerizable liquid crystal compound (3) can be improved.

( ^-X1- )
-X ¹ - represents -C(=O)O-, -OC(=O)-, -C(=S)O-, -OC(=S)-, -C(=O)S-, -SC(=O)-, -CH ₂ CH ₂ -, -CH=CH-, -C(=O)NH-, -NHC(=O)-, -CH ₂ O-, -OCH ₂ -, -CH ₂ S- or -SCH ₂ -. Among these, -X ¹ - is preferably -C(═O)O-, -OC(═O)-, -C(═S)O-, -OC(═S)-, -C(═O)S-, -SC(═O)-, -CH 2 CH 2 -, -CH 2 O-, -OCH 2 -, -CH ₂ S-, -SCH ₂ -, etc., which have small π bonding property, because the polymerizable liquid crystal compound (3) tends to have linearity and easy rotational motion around the molecular short axis. Among these, -C(═O)O-, -OC ₍ ═O)-, -CH ₂ CH ₂ -, -CH ₂ O-, -OCH ₂ -, ^{are more preferable, and -X 1} _- _is _still more preferably -C(═O)O- or -OC(═O)-. In another embodiment, —X ¹ — is preferably —CH ₂ CH ₂ —, —CH ₂ O—, or —OCH ₂ —.

( ^-X2- )
-X ² - represents a single bond, -C(=O)O-, -OC(=O)-, -C(=S)O-, -OC(=S)-, -C(=O)S-, -SC(=O)-, -CH ₂ CH ₂ -, -CH=CH-, -C(=O)NH-, -NHC(=O)-, -CH ₂ O-, -OCH ₂ -, -CH ₂ S-, or -SCH ₂ -.

From the viewpoint of enlarging the core of the polymerizable liquid crystal compound (3) and increasing the dichroism of the anisotropic dye film formed from the anisotropic dye film-forming composition, it is preferable that -C ^y - and -C≡C- are linked by a group with high linearity. Specifically, -X ² - is preferably a single bond, or -C(═O)O-, -OC(═O)-, -C(═S)O-, -OC(═S)-, -C(═O)S-, -SC(═O)-, -CH═CH-, -C(═O)NH-, or -NHC(═O)- having π-bonding properties, and is more preferably a single bond due to its higher linearity.

( ^-Q1 and ^-Q2 )
The polymerizable group in ^-Q1 and ^-Q2 is a group having a partial structure capable of being polymerized by light, heat, and/or radiation, and is a functional group or atomic group necessary for ensuring the function of polymerization. From the viewpoint of producing an anisotropic dye film, the polymerizable group is preferably a photopolymerizable group.

The polymerizable group includes, for example, an acryloyl group, a methacryloyl group, an acryloyloxy group, a methacryloyloxy group, an acryloylamino group, a methacryloylamino group, a vinyl group, a vinyloxy group, an ethynyl group, an ethynyloxy group, a 1,3-butadienyl group, a 1,3-butadienyloxy group, an oxiranyl group, an oxetanyl group, a glycidyl group, a glycidyloxy group, a styryl group, a styryloxy group, and the like, and an acryloyl group, a methacryloyl group, , acryloyloxy group, methacryloyloxy group, acryloylamino group, methacryloylamino group, oxiranyl group, glycidyl group, and glycidyloxy group are preferred, acryloyl group, methacryloyl group, acryloyloxy group, methacryloyloxy group, acryloylamino group, methacryloylamino group, glycidyl group, and glycidyloxy group are more preferred, and acryloyloxy group, methacryloyloxy group, and glycidyloxy group are even more preferred.

(-R ¹ - and -R ² -)
The chain organic group in -R ¹ - and -R ² - is a divalent organic group that does not contain a cyclic structure such as the above-mentioned aromatic hydrocarbon ring, non-aromatic hydrocarbon ring, aromatic heterocycle, or non-aromatic heterocycle.
Examples of such a chain organic group include -(alkylene group)-, -O-(alkylene group)-, -S-(alkylene group)-, -NH-(alkylene group)-, -N(alkyl)-(alkylene group)-, -OC(=O)-(alkylene group)-, and -C(=O)O-(alkylene group)-.

Examples of the alkylene group in these chain organic groups include linear or branched alkylene groups having 1 to 25 carbon atoms. The carbon-carbon bond of the alkylene group may be partially unsaturated. One or more methylene groups contained in the alkylene group may be displaced by -O-, -S-, -NH-, -N(R ^m )-, -C(═O)-, -C(═O)-O-, -C(═O)-NH-, -CHF-, -CF ₂ -, -CHCl-, or -CCl ₂ -. R ^m represents a linear or branched alkyl group having 1 to 6 carbon atoms.

The alkylene group in these chain organic groups is preferably a straight-chain alkylene group having 1 to 25 carbon atoms, in which some of the carbon atoms may be unsaturated, and in which one or more methylene groups contained in the alkylene group may be replaced (displaced) by the above-mentioned groups, due to their high molecular linearity.

The number of atoms in the main chain (meaning the longest chain portion in the chain organic group) in the chain organic group is preferably 3 to 25, more preferably 5 to 20, and even more preferably 6 to 20.

As the chain organic group, -(CH ₂ ) _r -CH ₂ -, -O-(CH ₂ ) _r -CH ₂ -, -(O) _r1 -(CH ₂ CH ₂ O) _r2 -(CH ₂ ) _r3 -, -(O) _r1 -(CH ₂ ) _r2 -(CH ₂ CH ₂ O) _r3 - are preferred. In these formulas, r is an integer of 1 to 24, preferably an integer of 2 to 24, more preferably an integer of 4 to 19, and even more preferably an integer of 5 to 19. In addition, in these formulas, r1, r2, and r3 each independently represent an integer, and the number of atoms in the main chain (meaning the longest chain portion in the chain organic group) in the chain organic group is appropriately adjusted to be preferably 3 to 25, more preferably 5 to 20, and even more preferably 6 to 20.

Each of -R ¹ - and -R ² - is preferably independently -(alkylene group)- or -O-(alkylene group)-, and more preferably -(alkylene group)- or -O-(alkylene group)-. In one embodiment, the chain organic group in -R ¹ - and -R ² - is -(alkylene group)-, and in another embodiment, it is -O-(alkylene group)-.

When -X ¹ - and -R ¹ - or -X ¹ - and -R ² - are bonded to each other as in the formula (3B) or (3E), or when -A ¹³ - in the formula (3B) is a single bond or when -A ¹¹ - in the formula (3E) is a single bond and -R ¹ - or -R ² - is bonded to -Y ¹ - or -Y ² -, it is preferable that -R ¹ - or -R ² - which is directly bonded to -X ¹ -, -Y ¹ - or -Y ² - is -(alkylene group)-.

In addition to the above, -R ¹ - or -R ² - which is not directly bonded to -X ¹ -, -Y ¹ - or -Y ² - is preferably -O-(alkylene group)-.

(Divalent Organic Groups in -A ¹¹ -, -A ¹² - and -A ¹³ -)
The divalent organic group in -A ¹¹ -, -A ¹² - and -A ¹³ - is preferably a group represented by the following formula (5).

^-Q3- (5)
(In formula (6), ^Q3 represents a hydrocarbon ring group or a heterocyclic group.)

The hydrocarbon ring group in -Q ³ - includes an aromatic hydrocarbon ring group and a non-aromatic hydrocarbon ring group.
The aromatic hydrocarbon ring group includes an unlinked aromatic hydrocarbon ring group and a linked aromatic hydrocarbon ring group.

The non-linked aromatic hydrocarbon ring group is a divalent group of a monocyclic or condensed aromatic hydrocarbon ring, and preferably has 6 to 20 carbon atoms because the appropriate core size provides good molecular orientation. The non-linked aromatic hydrocarbon ring group more preferably has 6 to 15 carbon atoms. Examples of aromatic hydrocarbon rings include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzpyrene ring, a chrysene ring, a triphenylene ring, an acenaphthene ring, a fluoranthene ring, and a fluorene ring.

　The linked aromatic hydrocarbon ring group is a divalent group in which a plurality of monocyclic or condensed aromatic hydrocarbon rings are bonded by single bonds and have a bond on an atom constituting the ring. The number of carbon atoms in the monocyclic or condensed ring is preferably 6 to 20 because the appropriate core size provides good orientation. The number of carbon atoms in the linked aromatic hydrocarbon ring group is more preferably 6 to 15. Examples of the linked aromatic hydrocarbon ring group include a divalent group in which a first monocyclic or condensed aromatic hydrocarbon ring having 6 to 20 carbon atoms is bonded by a single bond to a second monocyclic or condensed aromatic hydrocarbon ring having 6 to 20 carbon atoms, which has a first bond on an atom constituting the ring of the first monocyclic or condensed aromatic hydrocarbon ring having 6 to 20 carbon atoms, and a second bond on an atom constituting the ring of the second monocyclic or condensed aromatic hydrocarbon ring having 6 to 20 carbon atoms. Specific examples of the linked aromatic hydrocarbon ring group include biphenyl-4,4'-diyl groups.

As the aromatic hydrocarbon ring group, a non-linked aromatic hydrocarbon ring group is preferable because it optimizes the intermolecular interaction acting between liquid crystal compounds, thereby improving the molecular alignment.
Of these, the aromatic hydrocarbon ring group is preferably a divalent group of a benzene ring or a divalent group of a naphthalene ring, and more preferably a divalent group of a benzene ring (phenylene group). As the phenylene group, a 1,4-phenylene group is preferable. When -Q ³ - is one of these groups, the linearity of the liquid crystal molecules is increased, and the effect of improving molecular alignment tends to be obtained.

As an unlinked non-aromatic hydrocarbon ring group, a divalent group of cyclohexane (cyclohexanediyl group) is preferred. As a cyclohexanediyl group, a cyclohexane-1,4-diyl group is preferred.

The heterocyclic group in -Q ³ - includes an aromatic heterocyclic group and a non-aromatic heterocyclic group.

Aromatic heterocycles include a furan ring, a benzofuran ring, a thiophene ring, a benzothiophene ring, a pyrrole ring, a pyrazole ring, an imidazole ring, a thiazole ring, an oxadiazole ring, an indole ring, a carbazole ring, a pyrroloimidazole ring, a pyrrolopyrazole ring, a pyrrolopyrrole ring, a thienopyrrole ring, a thienothiophene ring, a furopyrrole ring, a furofuran ring, a thienofuran ring, a thienothiazole ring, a benzisoxazole ring, a benzisothiazole ring, a benzimidazole ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinoxaline ring, a phenanthridine ring, a quinazoline ring, a quinazolinone ring, and an azulene ring.

The aromatic hydrocarbon ring group, non-aromatic hydrocarbon ring group, aromatic heterocyclic group and non-aromatic heterocyclic group in -Q ³ - may each be substituted with one or more groups selected from the group consisting of -R ⁿ , -OH, -O-R ⁿ , -O-C(═O)-R ⁿ , -NH ₂ , -NH-R ⁿ , -N(R ^n' )-R ⁿ , -C(═O)-R ⁿ , -C( ^═O )-O-R ⁿ , -C(═O)-NH ₂ , -C(═O)-NH-R n, -C(═O)-N(R ^n' )-R ⁿ , -SH, -S-R ⁿ , trifluoromethyl group, sulfamoyl group, carboxy group, sulfo group, cyano group, nitro group and halogen. Each of --R ⁿ and --R ^n' independently represents a linear or branched alkyl group having 1 to 6 carbon atoms.

The aromatic hydrocarbon ring group, non-aromatic hydrocarbon ring group, aromatic heterocyclic group and non-aromatic heterocyclic group in -Q ³ - are each preferably independently unsubstituted or substituted with a methyl group, a methoxy group, a fluorine atom, a chlorine atom or a bromine atom, and more preferably unsubstituted, in terms of high linearity of the molecular structure, and ease of association of the polymerizable liquid crystal compounds (3) with each other to exhibit a liquid crystal state.

The substituents possessed by the aromatic hydrocarbon ring group, non-aromatic hydrocarbon ring group, aromatic heterocyclic group and non-aromatic heterocyclic group in -Q ³ - may be the same or different, and the aromatic hydrocarbon ring group, non-aromatic hydrocarbon ring group, aromatic heterocyclic group and non-aromatic heterocyclic group may be entirely substituted, entirely unsubstituted, or partially substituted and partially unsubstituted.

The substituents possessed by the divalent organic groups in -A ¹¹ -, -A ¹² -, and -A ¹³ - may be the same or different, and all of the divalent organic groups in -A ¹¹ -, -A ¹² -, and -A ¹³ - may be substituted, all of them may be unsubstituted, or some of them may be substituted and some of them may be unsubstituted.

-Q ³ - is preferably a hydrocarbon ring group, more preferably a phenylene group or a cyclohexanediyl group, and further preferably ^a 1,4-phenylene group or a cyclohexane-1,4-diyl group, since the linearity of the molecular structure of the polymerizable liquid crystal compound (3) can be increased.

As the divalent organic group of -A ¹¹ -, -A ¹² - and -A ¹³ -, -Q ³ - is preferably a hydrocarbon ring group, i.e., the divalent organic group is preferably a hydrocarbon ring group. As the divalent organic group, a phenylene group or a cyclohexanediyl group is more preferable, and a 1,4-phenylene group or a cyclohexane-1,4-diyl group is even more preferable because the linearity of the molecular structure of the polymerizable liquid crystal compound (3) can be increased.

In the polymerizable liquid crystal compound (3), it is preferable that one of -A ¹¹ -, -A ¹² -, and -A ¹³ - is a partial structure represented by formula (4), and the other two are each independently a divalent organic group. Furthermore, among -A ¹¹ -, -A ¹² -, and -A ¹³ -, it is preferable that -C ^y - of the partial structure represented by formula (4) is a hydrocarbon ring group, and it is particularly preferable that the divalent organic group is a hydrocarbon ring group. Furthermore, it is preferable that the hydrocarbon ring group is a 1,4-phenylene group or a cyclohexane-1,4-diyl group. Furthermore, it is preferable that one of -A ¹¹ - and -A ¹³ - is a cyclohexane-1,4-diyl group.

It is more preferable that one of -A ¹¹ - and -A ¹³ - is a partial structure represented by formula (4), and the remaining one and -A ¹² - are divalent organic groups. In this case, it is preferable that one of -A ¹¹ - and -A ¹³ - which is a divalent organic group is a cyclohexane-1,4-diyl group, and it is particularly preferable that -A ¹² - is a 1,4-phenylene group.

(-Y ¹ - and -Y ² -)
Each of -Y ¹ - and -Y ² - independently represents a single bond, -C(=O)O-, -OC(=O)-, -C(=S)O-, -OC(=S)-, -C(=O)S-, -SC(=O)-, -CH ₂ CH ₂ -, -CH=CH-, -C≡C-, -C(=O)NH-, -NHC(=O)-, -CH ₂ O-, -OCH ₂ -, -CH ₂ S-, or -SCH ₂ -. Since the polymerizable liquid crystal compound (3) tends to have linearity and easy rotational motion around the molecular short axis, -Y ¹ - and -Y ² - are each independently preferably a single bond, -C(=O)O-, -OC(=O)-, -C(=S)O-, -OC(=S)-, -C(=O)S-, -SC(=O)-, -CH ₂ CH ₂ -, -CH=CH-, -C(=O)NH-, -NHC(=O)-, -CH ₂ O-, -OCH ₂ -, -CH ₂ S- or -SCH ₂ -, which have small π-bonding property, and more preferably a single bond, -C(=O)O-, -OC(=O)-, -CH ₂ CH ₂ -, -CH ₂ O- or -OCH ₂ -.

When -X ¹ - and -Y ¹ - or -X ¹ - and -Y ² - are bonded to each other as in the formulae (3A), (3C), (3D) and (3F), -Y ¹ - bonded to -X ¹ - or -Y ² - bonded to -X ¹ - is preferably a single bond. The other of -X ¹ -, -Y ¹ - and -Y ² - is preferably -C(═O)O- or -OC(═O)-.

When -X ¹ - is not bonded to either -Y ¹ - or -Y ² - as in the formula (3B) or (3E), -X ¹ - is preferably -CH ₂ CH ₂ -, -CH ₂ O-, or -OCH ₂ -, and both -Y ¹ - and -Y ² - are preferably -C(=O)O- or -OC(=O)-.

(k)
k is 1 or 2. In one embodiment, k is preferably 1. In another embodiment, k is preferably 2.
When k is 2, each -Y ² - may be the same or different, and each -A ¹³ - may be the same or different.

(Preferred Structure)
As the polymerizable liquid crystal compound (3), a compound represented by the above formula (3A), (3B), (3E) or (3F) is preferable because it optimizes the intermolecular interaction acting between the liquid crystal compounds and has an appropriate core size, resulting in good molecular orientation.

In addition, the polymerizable liquid crystal compound used in the present invention is preferably a low molecular weight polymerizable liquid crystal compound, since it tends to provide good molecular orientation, and is particularly preferably a low molecular weight polymerizable liquid crystal compound that does not have a copolymer structure.

The molecular weight of the low molecular weight polymerizable liquid crystal compound is preferably 2000 or less, more preferably 1500 or less, and even more preferably 1000 or less. There is no particular lower limit, but 400 or more is preferable, and 500 or more is more preferable. The molecular weight range is preferably 400 to 2000, more preferably 400 to 1500, and particularly preferably 500 to 1000. The molecular weight of the polymerizable liquid crystal compound is the sum of the atomic weights contained in the polymerizable liquid crystal compound molecule.

(Specific Examples of Polymerizable Liquid Crystal Compounds)
Specific examples of the polymerizable liquid crystal compound contained in the composition of the present invention include, but are not limited to, the polymerizable liquid crystal compounds described below. In the following exemplary formulas, C ₆ H ₁₃ represents an n-hexyl group, and C ₅ H ₁₁ represents an n-pentyl group.

(Liquid Crystal Compound Content)
The liquid crystal compound contained in the composition of the present invention is preferably a polymerizable liquid crystal compound (3). The composition of the present invention may contain only one type of polymerizable liquid crystal compound alone, or may contain two or more types in any combination and ratio.

The content of the liquid crystal compound in the composition of the present invention (when two or more liquid crystal compounds are used in combination, the total content of each compound) is preferably 50 parts by mass or more, more preferably 55 parts by mass or more, and preferably 99 parts by mass or less, and more preferably 98 parts by mass or less, relative to the solid content (100 parts by mass) of the composition. If the content of the liquid crystal compound in the composition is between the above lower limit and the above upper limit, the alignment of the liquid crystal molecules tends to be high.

The composition of the present invention may contain one or more polymerizable or non-polymerizable liquid crystal compounds other than the polymerizable liquid crystal compound (3). However, from the viewpoint of obtaining the effect of the present invention more effectively by using the polymerizable liquid crystal compound (3), the proportion of the polymerizable liquid crystal compound (3) in the total amount of the liquid crystal compounds contained in the composition of the present invention (100% by mass) is preferably 5% by mass or more, more preferably 10% by mass or more, and particularly preferably 15 to 100% by mass.

(Isotropic phase appearance temperature)
From the viewpoint of processing, the polymerizable liquid crystal compound contained in the composition of the present invention preferably has an isotropic phase appearance temperature of 160° C. or lower, more preferably 140° C. or lower, even more preferably 115° C. or lower, even more preferably 110° C. or lower, and particularly preferably 105° C. or lower.
Here, the isotropic phase appearance temperature means the phase transition temperature from liquid crystal to liquid and the phase transition temperature from liquid to liquid crystal. In the present invention, it is preferable that at least one of these phase transition temperatures is equal to or lower than the above upper limit, and it is more preferable that both of these phase transition temperatures are equal to or lower than the above upper limit.

(Method for producing polymerizable liquid crystal compound)
The polymerizable liquid crystal compound contained in the composition of the present invention can be produced by combining known chemical reactions such as an alkylation reaction, an esterification reaction, an amidation reaction, an etherification reaction, an ipso substitution reaction, and a coupling reaction using a metal catalyst.
For example, the polymerizable liquid crystal compound contained in the composition of the present invention can be synthesized according to the method described in the Examples below or the method described on pages 449 to 468 of "Liquid Crystal Handbook" (Maruzen Co., Ltd., published on October 30, 2000).

(Relationship between polymerizable liquid crystal compound and dye)
From the viewpoint of facilitating improvement in the orientation of an anisotropic dye film formed using the composition of the present invention, in the composition of the present invention, it is preferable that the difference between the molecular length of the polymerizable liquid crystal compound and the molecular length of the dye is small, since this leads to stronger intermolecular interaction between the liquid crystal molecules and the dye molecules and makes it difficult for the dye molecules to inhibit association between the liquid crystal molecules.

Therefore, in the composition of the present invention, it is preferable that the ratio (r n1 /r _n2 ) of the number of ring structures (r _n1 ) possessed by the polymerizable liquid crystal compound contained in the composition to the number of ring structures (r _n2 ) possessed by the dye contained in the composition is _0.6 to 1.5.
In addition, a fused ring in which two or more rings are fused is counted as one ring structure.

Here, the number of ring structures (r _n2 ) possessed by compound (2) represented by formula (2) is the sum of B ¹ , B ² , B ³ and B ⁴ in the formula, and specifically, when n is 0, r _n2 is 4; when n is 1, r _n2 is 5; and when n is 2, r _n2 is 6.
Even if N(-RB ¹ )RB ² is a cyclic functional group such as a pyrrolidinyl group or a piperidinyl group, the ring structure contained in N(-RB ¹ )RB ² is not included in the number (r _n2 ) of ring structures contained in compound (2) represented by formula (2).

More specifically, when n is 0, r _n2 is 4, so r _n1 is 3, 4, 5, or 6; when n is 1, r _n2 is 5, so r _n1 is preferably 4, 5, 6, or 7, since the ratio (r n1 /r n2 ) of the number of ring structures (r _n1 ) possessed by the polymerizable liquid crystal compound contained in the composition for forming an anisotropic dye film to the number of ring structures (r _n2 ) possessed by compound ( ₂ ) contained in the composition for forming an anisotropic dye film is _0.6 to 1.5.

The number of ring structures (r _n2 ) contained in compound (12) represented by formula (12) is the sum of the ring structures contained in A ²¹ , A ²² , A ²³ and -X ²⁰ in the formula, and specifically, when n1 is 1 and m1 is 1, r _n2 is 3; when n1 is 1 and m1 is 2, r _n2 is 4; when n1 is 2 and m1 is 1, r _n2 is 4; when n1 is 2 and m1 is 2, r _n2 is 5; and when n1 is 3 and m1 is 1, r _n2 is 5.
Even if -Y ²⁰ is a cyclic functional group such as a pyrrolidinyl group or a piperidinyl group, the ring structure contained in -Y ²⁰ is not included in the number (r _n2 ) of ring structures contained in compound (12) represented by formula (12).

More specifically, when n1 is 1 and m1 is 1, r _n2 is 3, so r _n1 is 2, 3, or 4; when n1 is 1 and m1 is 2, r _n2 is 4, so r _n1 is 3, 4, 5, or 6; when n1 is 2 and m1 is 1, r _n2 is 4, so r _n1 is 3, 4, 5, or 6; when n1 is 2 and m1 is 2, r _n2 is 5, so r _n1 is 3, 4, 5, 6, or 7; when n1 is 3 and m1 is 1, r _n2 is 5, so r _n1 is 3, 4, 5, 6, or 7, then the ratio (r _n1 /r _n2 ) of the number of ring structures possessed by the polymerizable liquid crystal compound contained in the composition for forming an anisotropic dye film to the number of ring structures possessed by the compound of the second invention contained in the composition for forming an _anisotropic dye film _is ) is preferably 0.6 to 1.5.

The number (r _n1 ) of ring structures in the polymerizable liquid crystal compound contained in the composition of the present invention does not include ring structures (such as oxirane rings and oxetane rings) contained in the polymerizable groups in the polymerizable liquid crystal compound.

[Polymerization initiator]
The composition of the present invention may contain a polymerization initiator, if necessary.

The polymerization initiator is a compound that can initiate the polymerization reaction of a polymerizable liquid crystal compound. As the polymerization initiator, a photopolymerization initiator that generates active radicals by the action of light is preferable.

Usable polymerization initiators include, for example, titanocene derivatives; biimidazole derivatives; halomethylated oxadiazole derivatives; halomethyl-s-triazine derivatives; alkylphenone derivatives; oxime ester derivatives; benzoins; benzophenone derivatives; acylphosphine oxide derivatives; iodonium salts; sulfonium salts; anthraquinone derivatives; acetophenone derivatives; thioxanthone derivatives; benzoic acid ester derivatives; acridine derivatives; phenazine derivatives; anthrone derivatives, etc.

Among these photopolymerization initiators, alkylphenone derivatives, oxime ester derivatives, biimidazole derivatives, acetophenone derivatives, and thioxanthone derivatives are more preferred.

Specific examples of titanocene derivatives include dicyclopentadienyltitanium dichloride, dicyclopentadienyltitanium bisphenyl, dicyclopentadienyltitanium bis(2,3,4,5,6-pentafluorophenyl-1-yl), dicyclopentadienyltitanium bis(2,3,5,6-tetrafluorophenyl-1-yl), dicyclopentadienyltitanium bis(2,4,6-trifluorophenyl-1-yl), dicyclopentadienyltitanium Examples include titanium di(2,6-difluorophenyl-1-yl), dicyclopentadienyltitanium di(2,4-difluorophenyl-1-yl), di(methylcyclopentadienyl)titanium bis(2,3,4,5,6-pentafluorophenyl-1-yl), di(methylcyclopentadienyl)titanium bis(2,6-difluorophenyl-1-yl), and dicyclopentadienyltitanium [2,6-difluoro-3-(pyrro-1-yl)-phenyl-1-yl].

Biimidazole derivatives include 2-(2'-chlorophenyl)-4,5-diphenylimidazole dimer, 2-(2'-chlorophenyl)-4,5-bis(3'-methoxyphenyl)imidazole dimer, 2-(2'-fluorophenyl)-4,5-diphenylimidazole dimer, 2-(2'-methoxyphenyl)-4,5-diphenylimidazole dimer, (4'-methoxyphenyl)-4,5-diphenylimidazole dimer, etc.

Halomethylated oxadiazole derivatives include 2-trichloromethyl-5-(2'-benzofuryl)-1,3,4-oxadiazole, 2-trichloromethyl-5-[β-(2'-benzofuryl)vinyl]-1,3,4-oxadiazole, 2-trichloromethyl-5-[β-(2'-(6''-benzofuryl)vinyl)]-1,3,4-oxadiazole, and 2-trichloromethyl-5-furyl-1,3,4-oxadiazole.

Halomethyl-s-triazine derivatives include 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphthyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-ethoxynaphthyl)-4,6-bis(trichloromethyl)-s-triazine, and 2-(4-ethoxycarbonylnaphthyl)-4,6-bis(trichloromethyl)-s-triazine.

Alkylphenone derivatives include diethoxyacetophenone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butan-1-one, 4-dimethylaminoethyl benzoate, 4-dimethylaminoisoamyl benzoate, 4-diethylaminoacetophenone, 4-dimethylaminopropiophenone, 2-ethylhexyl-1,4-dimethylaminobenzoate, 2,5-bis(4-diethylaminobenzal)cyclohexanone, 7-diethylamino-3-(4-diethylaminobenzoyl)coumarin, and 4-(diethylamino)chalcone.

Oxime ester derivatives include 2-(benzoyloxyimino)-1-[4-(phenylthio)phenyl]-1-octanone, O-acetyl-1-[6-(2-methylbenzoyl)-9-ethyl-9H-carbazol-3-yl]ethanone oxime, and the oxime ester derivatives described in JP 2000-80068 A, JP 2006-36750 A, WO 2009/131189, etc.

Examples of benzoins include benzoin, benzoin methyl ether, benzoin phenyl ether, benzoin isobutyl ether, and benzoin isopropyl ether.

Examples of benzophenone derivatives include benzophenone, Michler's ketone, 2-methylbenzophenone, 3-methylbenzophenone, 4-methylbenzophenone, 2-chlorobenzophenone, 4-bromobenzophenone, 2-carboxybenzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone.

Acylphosphine oxide derivatives include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis-(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide, and bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide.

Iodonium salts include diphenyliodonium tetrakis(pentafluorophenyl)borate, diphenyliodonium hexafluorophosphate, diphenyliodonium hexafluoroantimonate, and di(4-nonylphenyl)iodonium hexafluorophosphate.

Sulfonium salts include triphenylsulfonium hexafluorophosphate, triphenylsulfonium hexafluoroantimonate, triphenylsulfonium tetrakis(pentafluorophenyl)borate, diphenyl[4-(phenylthio)phenyl]sulfonium hexafluorophosphate, 4,4'-bis[diphenylsulfonio]diphenylsulfide bishexafluorophosphate, 4,4'-bis[di(β-hydroxyethoxy)phenylsulfonio]diphenylsulfide bishexafluoroantimonate, 4,4'-bis[di(β-hydroxyethoxy)phenylsulfonio]diphenylsulfide bishexafluorophosphate -, 7-[di(p-toluyl)sulfonio]-2-isopropylthioxanthone hexafluoroantimonate, 7-[di(p-toluyl)sulfonio]-2-isopropylthioxanthone tetrakis(pentafluorophenyl)borate, 4-phenylcarbonyl-4'-diphenylsulfonio-diphenylsulfide hexafluorophosphate, 4-(p-tert-butylphenylcarbonyl)-4'-diphenylsulfonio-diphenylsulfide hexafluoroantimonate, 4-(p-tert-butylphenylcarbonyl)-4'-di(p-toluyl)sulfonio-diphenylsulfide tetrakis(pentafluorophenyl)borate, etc.

Anthraquinone derivatives include 2-methylanthraquinone, 2-ethylanthraquinone, 2-t-butylanthraquinone, 1-chloroanthraquinone, etc.

Acetophenone derivatives include 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxyacetophenone, 1-hydroxycyclohexyl phenyl ketone, α-hydroxy-2-methylphenylpropanone, 1-hydroxy-1-methylethyl-(p-isopropylphenyl)ketone, 1-hydroxy-1-(p-dodecylphenyl)ketone, 2-methyl-(4'-methylthiophenyl)-2-morpholino-1-propanone, 1,1,1-trichloromethyl-(p-butylphenyl)ketone, etc.

Thioxanthone derivatives include thioxanthone, 2-ethylthioxanthone, 2-isopropylthioxanthone, 2-chlorothioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, etc.

Benzoic acid ester derivatives: Examples include ethyl p-dimethylaminobenzoate, ethyl p-diethylaminobenzoate, etc.

Acridine derivatives include 9-phenylacridine, 9-(p-methoxyphenyl)acridine, etc.

Phenazine derivatives include 9,10-dimethylbenzphenazine, etc.

Anthrone derivatives include benzanthrone, etc.

The polymerization initiator may be used alone or in combination with two or more types.

As the polymerization initiator, a commercially available product can also be used.
Examples of commercially available products include IRGACURE (registered trademark, the same applies below) 250, IRGACURE 651, IRGACURE 184, DAROCURE 1173, IRGACURE 2959, IRGACURE 127, IRGACURE 907, IRGACURE 369, IRGACURE 379EG, LUCIRIN TPO, IRGACURE 819, and IRGACURE 784, OXE-01, OXE-02 (all manufactured by BASF); Seikuol (registered trademark) BZ, Z, and BEE (manufactured by Seiko Chemical Co., Ltd.); Kayacure (registered trademark) BP100, and UVI-6992 (manufactured by The Dow Chemical Company); ADEKA OPTOMER SP-152, and SP-170 (manufactured by ADEK Corporation). A); TAZ-A, and TAZ-PP (manufactured by Nippon SiberHegner Co., Ltd.); and TAZ-104 (manufactured by Sanwa Chemical Co., Ltd.); TRONLYTR-PBG-304, TRONLYTR-PBG-309, TRONLYTR-PBG-305, and TRONLYTR-PBG-314 (manufactured by CHANGZHOU TRONLY NEW ELECTRONIC MATERIALS CO., LTD.).

When the composition of the present invention contains a polymerization initiator, the content of the polymerization initiator in the composition of the present invention is usually 0.1 to 30 parts by mass, preferably 0.5 to 10 parts by mass, and more preferably 0.5 to 8 parts by mass, relative to 100 parts by mass of the polymerizable liquid crystal compound, from the viewpoint of not easily disturbing the orientation of the polymerizable liquid crystal compound.

If necessary, a polymerization accelerator may be used in combination with the polymerization initiator. Examples of the polymerization accelerator to be used include N,N-dialkylaminobenzoic acid alkyl esters such as N,N-dimethylaminobenzoic acid ethyl ester, mercapto compounds having a heterocycle such as 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, and 2-mercaptobenzimidazole, and mercapto compounds such as aliphatic polyfunctional mercapto compounds.
The polymerization accelerator may also be used alone or in combination of two or more kinds.

Sensitizing dyes may be used in combination for the purpose of increasing the sensitivity as required. Sensitizing dyes that are appropriate for the wavelength of the exposure light source are used. For example, xanthene dyes described in JP-A-4-221958 and JP-A-4-219756, etc.; coumarin dyes having a heterocycle described in JP-A-3-239703 and JP-A-5-289335, etc.; 3-ketocoumarin dyes described in JP-A-3-239703 and JP-A-5-289335, etc.; pyrromethene dyes described in JP-A-6-19240, etc.; and JP-A-47-2528 and JP-A-54-155292, etc. and dyes having a dialkylaminobenzene skeleton described in JP-B-45-37377, JP-A-48-84183, JP-A-52-112681, JP-A-58-15503, JP-A-60-88005, JP-A-59-56403, JP-A-2-69, JP-A-57-168088, JP-A-5-107761, JP-A-5-210240, and JP-A-4-288818.
The sensitizing dyes may also be used alone or in combination of two or more kinds.

[solvent]
The composition of the present invention may contain a solvent, if necessary.

The solvent that can be used in the composition of the present invention is not particularly limited as long as it can sufficiently disperse or dissolve the dye or other additives in the polymerizable liquid crystal compound. Examples of the solvent include alcohol solvents such as methanol, ethanol, ethylene glycol, isopropyl alcohol, propylene glycol, ethylene glycol methyl ether, ethylene glycol butyl ether, and propylene glycol monomethyl ether; ester solvents such as ethyl acetate, butyl acetate, ethylene glycol methyl ether acetate, γ-butyrolactone, propylene glycol methyl ether acetate, and ethyl lactate; ketone solvents such as acetone, methyl ethyl ketone, cyclopentanone, cyclohexanone, 2-heptanone, and methyl isobutyl ketone; aliphatic hydrocarbon solvents such as pentane, hexane, and heptane; aromatic hydrocarbon solvents such as toluene and xylene; nitrile solvents such as acetonitrile; ether solvents such as tetrahydrofuran, dimethoxyethane, ethylene glycol dimethyl ether, and ethylene glycol diethyl ether; fluorine-containing solvents such as perfluorobenzene, perfluorotoluene, perfluorodecalin, perfluoromethylcyclohexane, and hexafluoro-2-propanol; and chlorine-containing solvents such as chloroform, dichloromethane, chlorobenzene, and dichlorobenzene.
These solvents may be used alone or in combination of two or more.

The solvent is preferably one that can dissolve the polymerizable liquid crystal compound and the dye, and more preferably one that completely dissolves the polymerizable liquid crystal compound and the dye. The solvent is also preferably one that is inactive in the polymerization reaction of the polymerizable liquid crystal compound. From the viewpoint of applying the composition of the present invention described later, the solvent is also preferably one that has a boiling point in the range of 50 to 200°C.

When the composition of the present invention contains a solvent, the content of the solvent in the composition of the present invention is preferably 50 to 98 mass% relative to the total amount (100 mass%) of the composition of the present invention. In other words, the solid content in the composition of the present invention is preferably 2 to 50 mass%.
When the solid content in the composition of the present invention is equal to or less than the upper limit, the viscosity of the composition of the present invention does not become too high, the thickness of the obtained polarizing film becomes uniform, and unevenness in the polarizing film tends to be less likely to occur.

The solid content of the composition of the present invention can be determined taking into consideration the thickness of the polarizing film to be produced.

The viscosity of the composition of the present invention is not particularly important as long as a uniform film without uneven thickness is produced by the coating method described below. From the viewpoint of obtaining uniformity of thickness over a large area, productivity such as coating speed, and in-plane uniformity of optical properties, the viscosity of the composition of the present invention is preferably 0.1 mPa·s or more, and preferably 500 mPa·s or less, more preferably 100 mPa·s or less, and even more preferably 50 mPa·s or less.

[Other additives]
The composition of the present invention may further contain, as necessary, other additives such as a polymerization inhibitor, a polymerization aid, a polymerizable non-liquid crystal compound, a surfactant, a leveling agent, a coupling agent, a pH adjuster, a dispersant, an antioxidant, an organic or inorganic filler, an organic or inorganic nanosheet, an organic or inorganic nanofiber, or a metal oxide, in addition to the above-mentioned polymerization initiator, as components other than the dye and the polymerizable liquid crystal compound.
The inclusion of these additives may improve the coatability, stability, etc. of the composition of the present invention, and may also improve the stability of the anisotropic dye film formed from the composition of the present invention.

[Production method of the composition]
The method for producing the composition of the present invention is not particularly limited. For example, a dye containing compound (2) or the dye of the second invention, a polymerizable liquid crystal compound, a solvent and other additives as necessary are mixed, and the mixture is stirred and shaken at 0 to 80° C. to dissolve the dye. If these are poorly soluble, a homogenizer, a bead mill disperser, or the like may be used.

The method for producing the composition of the present invention may include a filtration step for the purpose of removing foreign matter from the composition.

The composition of the present invention may or may not be liquid crystal at any temperature after the solvent has been removed from the composition, but it is preferable that the composition exhibits liquid crystallinity at any temperature.

From the viewpoint of the coating process described below, the composition of the present invention from which the solvent has been removed preferably has an isotropic phase appearance temperature of less than 160°C, more preferably less than 140°C, even more preferably less than 115°C, even more preferably less than 110°C, and particularly preferably less than 105°C.

[Anisotropic dye film]
The anisotropic dye film of the present invention is formed using the composition of the present invention.
Therefore, the anisotropic dye film of the first invention contains a dye and one or both of a polymerizable liquid crystal compound and a polymer having a unit based on a polymerizable liquid crystal compound, and the dye contains compound (2).
The anisotropic dye film of the second invention includes a dye and one or both of a polymerizable liquid crystal compound and a polymer having a unit based on a polymerizable liquid crystal compound, and the dye includes the dye of the second invention.
Hereinafter, the "anisotropic dye film of the first invention" and the "anisotropic dye film of the second invention" will be collectively referred to as the "anisotropic dye film of the present invention."
The composition of the present invention for forming the anisotropic dye film of the present invention may be referred to as an "anisotropic dye film-forming composition".

The anisotropic dye film of the present invention may contain other components such as non-polymerizable liquid crystal compounds, polymerization initiators, polymerization inhibitors, polymerization aids, polymerizable non-liquid crystal compounds, non-polymerizable non-liquid crystal compounds, surfactants, leveling agents, coupling agents, pH adjusters, dispersants, antioxidants, organic/inorganic fillers, organic/inorganic nanosheets, organic/inorganic nanofibers, metal oxides, etc.

The anisotropic dye film of the present invention can function as a polarizing film that uses the anisotropy of light absorption to obtain linearly polarized light, circularly polarized light, elliptically polarized light, etc., and can also function as various anisotropic dye films with refractive anisotropy, conductive anisotropy, etc., depending on the film formation process and the selection of the composition containing the substrate and organic compound (dye or transparent material).

When the anisotropic dye film of the present invention is used as a polarizing element for a liquid crystal display or an antireflection film for an OLED, the orientation characteristics of the anisotropic dye film can be expressed by the dichroic ratio.
A dichroic ratio of 8 or more will enable the element to function as a polarizing element, but in the first invention, the dichroic ratio is preferably 23 or more, more preferably 25 or more, further preferably 30 or more, and particularly preferably 40 or more.
In the second invention, the dichroic ratio is preferably 13 or more, and more preferably 20 or more.
The higher the dichroic ratio of the anisotropic dye film, the more preferable it is.
When the dichroic ratio is equal to or more than the lower limit, the film is useful as an optical element, particularly a polarizing element, as described below.

When used as a polarizing element in an anti-reflection film for OLEDs, even if the performance of peripheral materials such as retardation films is low, if the performance of the polarizing element is high, the characteristics as an anti-reflection film will be improved. Therefore, if the performance of the polarizing element is high, it is easier to simplify the layer structure, and even a thin film structure can easily exhibit sufficient functionality, making it suitable for use in applications where it is used after being deformed, including folding and bending. It also makes it possible to keep costs low.

The dichroic ratio (D) in the present invention is expressed by the following formula when the dyes are uniformly oriented.
D = Az/Ay
Here, Az is the absorbance observed when the polarization direction of light incident on the anisotropic dye film is parallel to the orientation direction of the anisotropic dye, and Ay is the absorbance observed when the polarization direction of light incident on the anisotropic dye film is perpendicular to the orientation direction of the anisotropic dye.

There are no particular limitations on the absorbance (Az, Ay) as long as they are of the same wavelength, and any wavelength may be selected depending on the purpose. When expressing the degree of orientation of an anisotropic dye film, it is preferable to use a value corrected for visual sensitivity in a specific wavelength range of 350 nm to 800 nm for the anisotropic dye film, or a value at the maximum absorption wavelength in the visible range.

The transmittance of the anisotropic dye film of the present invention is preferably 25% or more, more preferably 35% or more, and particularly preferably 40% or more, at the wavelength of the intended use. When the anisotropic dye film of the present invention is used as a dye film having anisotropy over the entire visible light wavelength range, the transmittance of the anisotropic dye film in the visible light wavelength range is preferably 25% or more, more preferably 35% or more, and particularly preferably 40% or more. The transmittance of the anisotropic dye film of the present invention may be an upper limit according to the application. For example, when the degree of polarization is to be increased, the transmittance is preferably 50% or less. When the transmittance is in the above range, it is useful as an optical element described later, and is particularly useful as an optical element for liquid crystal displays used for color display and for antireflection films combining an anisotropic dye film and a retardation film.

The anisotropic dye film has a dry thickness of preferably 10 nm or more, more preferably 100 nm or more, and even more preferably 500 nm or more. The anisotropic dye film has a dry thickness of preferably 30 μm or less, more preferably 10 μm or less, even more preferably 5 μm or less, and especially preferably 3 μm or less. By having the anisotropic dye film have a thickness in the above range, there is a tendency to obtain a uniform orientation of the dye within the film and a uniform film thickness.

[Method of manufacturing anisotropic dye film]
The anisotropic dye film of the present invention is preferably produced by a wet film-forming method using the composition of the present invention.

The wet film-forming method referred to in this invention is a method in which an anisotropic dye film composition is applied and oriented on a substrate by some method. Therefore, the anisotropic dye film composition only needs to have fluidity, and may or may not contain a solvent. From the viewpoint of viscosity during application and film uniformity, it is more preferable for the composition to contain a solvent.

The liquid crystals and dyes in the anisotropic dye film may be oriented by shear during the coating process, or may be oriented during the drying process of the solvent. In addition, the liquid crystals and dyes may be oriented and laminated on the substrate through a process of heating after coating and drying to re-align the liquid crystals and dyes. In the wet film formation method, when the composition for anisotropic dye film is applied to the substrate, the dyes and liquid crystal compounds self-associate (a molecular association state such as a liquid crystal state) already in the composition for anisotropic dye film, or during the drying process of the solvent, or after the solvent has been completely removed, and orientation occurs in a small area. By applying an external field to this state, orientation can be achieved in a certain direction in a macroscopic region, and an anisotropic dye film with the desired performance can be obtained. In this respect, it differs from the method in which a polyvinyl alcohol (PVA) film or the like is dyed with a solution containing a dye and stretched, and the dye is oriented only in the stretching process. Here, the external field includes the influence of an orientation treatment layer previously applied to the substrate, shear force, magnetic field, electric field, heat, etc. These may be used alone or in combination. If necessary, a heating process may be performed.

The process of applying the anisotropic dye film composition onto a substrate to form a film, the process of applying an external field to orient the film, and the process of drying the solvent may be performed sequentially or simultaneously.

In the wet film formation method, examples of methods for applying the composition for forming an anisotropic dye film onto a substrate include a coating method, a dip coating method, an LB film formation method, and a known printing method. There is also a method of transferring the anisotropic dye film thus obtained onto another substrate.

Among these, it is preferable to apply the composition for forming an anisotropic dye film onto the substrate using a coating method.

The orientation direction of the anisotropic dye film may be different from the coating direction. In the present invention, the orientation direction of the anisotropic dye film refers to, for example, the transmission axis (polarization axis) or absorption axis of polarized light in the case of a polarizing film. In the case of a retardation film, the orientation direction refers to the fast axis or slow axis.

The method of applying the composition for anisotropic dye film to obtain an anisotropic dye film is not particularly limited, but examples include the method described in "Coating Engineering" by Harasaki Yuji (published by Asakura Publishing Co., Ltd. on March 20, 1971) on pages 253-277, the method described in "Creation and Application of Molecular Cooperative Materials" edited by Ichimura Kunihiro (published by CMC Publishing Co., Ltd. on March 3, 1998) on pages 118-149, and the method of applying the composition to a substrate having a stepped structure (which may be pre-treated for orientation) by slot die coating, spin coating, spray coating, bar coating, roll coating, blade coating, curtain coating, fountain coating, dip coating, etc. Among these, the slot die coating and bar coating methods are preferable because they can obtain an anisotropic dye film with high uniformity.

The die coater used in the slot die coating method is generally equipped with a coating machine that ejects the coating liquid, a so-called slit die. Slit dies are disclosed, for example, in JP-A-2-164480, JP-A-6-154687, JP-A-9-131559, "Fundamentals and Applications of Dispersion, Coating, and Drying" (2014, Techno System Co., Ltd., ISBN 9784924728707 C 305), "Wet Coating Technology for Displays and Optical Components" (2007, Information Organization, ISBN 9784901677752), and "Precision Coating and Drying Technology in the Electronics Field" (2007, Technical Information Association, ISBN 9784861041389). These known slit dies can be used to coat flexible materials such as films and tapes, as well as hard materials such as glass substrates.

Substrates used in the formation of the anisotropic dye film of the present invention include glass, triacetate, acrylic, polyester, polyimide, polyetherimide, polyetheretherketone, polycarbonate, cycloolefin polymer, polyolefin, polyvinyl chloride, triacetyl cellulose, or urethane-based films.

In order to control the orientation direction of the dye, the substrate surface may be subjected to an orientation treatment (orientation film) by a known method (rubbing method, method of forming grooves (fine groove structure) on the surface of the orientation film, method of using polarized ultraviolet light/polarized laser (photo-orientation method), orientation method by forming an LB film, orientation method by oblique deposition of inorganic material, etc.) described on pages 226-239 of "Liquid Crystal Handbook" (Maruzen Co., Ltd., published October 30, 2000). In particular, orientation treatment by rubbing method and photo-orientation method are preferable. Materials used in the rubbing method include polyvinyl alcohol (PVA), polyimide (PI), epoxy resin, acrylic resin, etc. Materials used in the photo-orientation method include polycinnamate, polyamic acid/polyimide, azobenzene, etc. When an orientation treatment layer is provided, it is thought that the liquid crystal compound and the dye are oriented by the influence of the orientation treatment of the orientation treatment layer and the shear force applied to the anisotropic dye film composition during application.

When applying the composition for anisotropic dye film, there are no particular limitations on the method of supplying the composition for anisotropic dye film or the supply interval. If the operation of supplying the coating liquid becomes complicated or the coating film thickness fluctuates when the coating liquid is started and stopped, it is desirable to apply the composition for anisotropic dye film while continuously supplying it when the anisotropic dye film is thin.

The speed at which the composition for anisotropic dye film is applied is usually 0.001 m/min or more, preferably 0.01 m/min or more, more preferably 0.1 m/min or more, even more preferably 1.0 m/min or more, and particularly preferably 5.0 m/min or more. The speed at which the composition for anisotropic dye film is applied is usually 400 m/min or less, preferably 200 m/min or less, more preferably 100 m/min or less, and even more preferably 50 m/min or less. When the application speed is in the above range, the anisotropy of the anisotropic dye film is obtained, and it tends to be possible to apply it uniformly.

The coating temperature for the anisotropic dye film composition is usually 0°C or higher and 100°C or lower, preferably 80°C or lower, and more preferably 60°C or lower.

The humidity during application of the anisotropic dye film composition is preferably 10% RH or higher, and preferably 80% RH or lower.

The anisotropic dye film may be subjected to an insolubilization treatment. Insolubilization refers to a treatment for reducing the solubility of a compound in the anisotropic dye film, thereby controlling the elution of the compound from the anisotropic dye film and increasing the stability of the film.
Specifically, film polymerization or overcoating is preferred from the standpoint of ease of post-processing and durability of the anisotropic dye film.

When polymerizing the film, the film in which the liquid crystal molecules and dye molecules are oriented is polymerized using light, heat, and/or radiation.

When polymerization is carried out using light or radiation, it is preferable to irradiate with active energy rays having a wavelength in the range of 190 to 450 nm.

The light source of the active energy ray having a wavelength of 190 to 450 nm is not particularly limited. Examples of the light source include lamp light sources such as xenon lamps, halogen lamps, tungsten lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, metal halide lamps, medium-pressure mercury lamps, low-pressure mercury lamps, carbon arcs, and fluorescent lamps; and laser light sources such as argon ion lasers, YAG lasers, excimer lasers, nitrogen lasers, helium cadmium lasers, and semiconductor lasers. When light of a specific wavelength is irradiated, an optical filter can also be used.
The exposure dose of the active energy rays is preferably 10 to 10,000 J/ ^m2 .

When polymerization is carried out using heat, it is preferable to carry it out in the range of 50 to 200°C, and even more preferable to carry it out in the range of 60 to 150°C.

Polymerization may be carried out using light, heat, and/or radiation, but photopolymerization or a combination of photopolymerization and thermal polymerization is preferred because the film formation process takes a short time and requires simple equipment.

[Optical elements]
The optical element of the present invention includes the anisotropic dye film of the present invention.

The optical element in this invention refers to a polarizing element that utilizes the anisotropy of light absorption to obtain linearly polarized light, circularly polarized light, elliptically polarized light, etc., a phase difference element, and an element that has functions such as refractive anisotropy and conductive anisotropy. These functions can be appropriately adjusted by selecting the anisotropic dye film formation process and the composition containing the substrate and organic compound (dye or transparent material).

The optical element of the present invention is most preferably used as a polarizing element.
The optical element of the present invention can be suitably used for applications such as flexible displays because a polarizing element can be obtained by forming an anisotropic dye film on a substrate by coating or the like.

The optical element may be provided with other layers to maintain or improve the functionality of the anisotropic dye film. Examples of other layers include layers that have the function of blocking specific wavelengths or layers that have the function of blocking specific substances (e.g., barrier films such as oxygen barrier films and water vapor barrier films) that are used to improve durability such as light resistance, heat resistance, and water resistance; wavelength cut filters or layers containing materials that absorb specific wavelengths that are used to change the color gamut or improve optical properties; etc.

[Polarizing element]
A polarizing element (hereinafter, sometimes referred to as "the polarizing element of the present invention") can be produced using the anisotropic dye film of the present invention.

The polarizing element of the present invention may have any other film (layer) as long as it has the anisotropic dye film of the present invention. For example, it can be manufactured by providing an alignment film on a substrate and forming the anisotropic dye film of the present invention on the surface of the alignment film.

The polarizing element is not limited to anisotropic dye films, and may be used in combination with an overcoat layer having functions such as improving polarization performance and mechanical strength; an adhesive layer or anti-reflection layer; an alignment film; a layer having optical functions such as a phase difference film, a brightness enhancement film, a reflective or anti-reflection film, a semi-transparent reflective film, or a diffusion film; etc. Specifically, the layers having the various functions described above may be laminated by coating or lamination, etc., and used as a laminate.

These layers can be provided as appropriate in accordance with the manufacturing process, characteristics, and functions, and there are no particular limitations on the position and order of lamination. For example, each layer may be formed on the anisotropic dye film, or on the opposite side of the substrate on which the anisotropic dye film is provided. Furthermore, the order in which each layer is formed may be either before or after the anisotropic dye film is formed.

These layers with optical functions can be formed by the following methods:

The layer that functions as a retardation film can be formed by coating or laminating a retardation film onto other layers that make up the polarizing element. The retardation film can be formed, for example, by carrying out the stretching treatment described in JP-A-2-59703 and JP-A-4-230704, or the treatment described in JP-A-7-230007.

The layer that functions as a brightness enhancement film can be formed by coating or laminating the brightness enhancement film onto other layers that make up the polarizing element. The brightness enhancement film can be formed, for example, by forming micropores using the methods described in JP-A-2002-169025 and JP-A-2003-29030, or by superimposing two or more cholesteric liquid crystal layers that have different central wavelengths of selective reflection.

A layer that functions as a reflective film or semi-transparent reflective film can be formed, for example, by coating or laminating a thin metal film obtained by vapor deposition or sputtering onto other layers that make up the polarizing element.

The layer that functions as a diffusion film can be formed, for example, by coating the other layers that make up the polarizing element with a resin solution that contains fine particles.

　Layers that function as retardation films or optical compensation films can be formed by applying liquid crystal compounds such as discotic liquid crystal compounds, nematic liquid crystal compounds, smectic liquid crystal compounds, and cholesteric liquid crystal compounds to other layers that make up the polarizing element and orienting them. In this case, an orientation film may be provided on the substrate, and the retardation film or optical compensation film may be formed on the surface of the orientation film.

When the anisotropic dye film of the present invention is used as an anisotropic dye film in various display elements such as liquid crystal elements (LCDs) and organic electroluminescence elements (OLEDs), the anisotropic dye film of the present invention may be formed directly on the surface of an electrode substrate or the like that constitutes these display elements, or a substrate on which the anisotropic dye film of the present invention is formed may be used as a component of these display elements.

The present invention will be described in more detail below with reference to examples. The present invention is not limited to the following examples as long as it does not depart from the gist of the present invention.
In the following description, "parts" means "parts by mass".

[Method for identifying liquid crystal phase]
The liquid crystallinity of the obtained composition was observed by differential scanning calorimetry (Seiko Instruments Inc. "DSC220CU"), X-ray structural analysis (Rigaku Corporation "NANO-Viewer"), and a polarizing microscope (Nikon Instech Inc. "Eclipse LV100N POL") equipped with a hot stage (Toyo Corporation "HCS302-LN190"), and the composition was identified as being liquid crystal in accordance with the method described on pages 9 to 50 and 117 to 176 of "Liquid Crystal Handbook" (Maruzen Co., Ltd., published on October 30, 2000).

[Measurement of transmittance for polarized light in the absorption axis/polarization axis direction of anisotropic dye film and calculation of dichroic ratio]
The transmittance of the resulting anisotropic dye film for polarized light in the absorption axis/polarization axis direction was measured using a spectrophotometer equipped with a Glan-Thompson polarizer (manufactured by Otsuka Electronics Co., Ltd., product name "RETS-100").
Linearly polarized measurement light was incident on the anisotropic dye film, and the transmittance for polarized light in the absorption axis direction of the anisotropic dye film and the transmittance for polarized light in the polarization axis direction of the anisotropic dye film were measured, and the dichroic ratio (D) was calculated by the following formula.
D = Az/Ay
(Wherein,
Ay=-log(Ty);
Az=-log(Tz);
Tz is the transmittance of the anisotropic dye film for polarized light in the absorption axis direction;
Ty is the transmittance of the anisotropic dye film for polarized light in the direction of the polarization axis.

Specifically, the composition was injected in an isotropic phase into a sandwich cell (cell gap: 8.0 μm or 10.0 μm, polyimide film previously rubbed with cloth) with a polyimide alignment film (LX1400, Hitachi Chemical DuPont Microsystems) formed on a glass substrate, and an anisotropic dye film was obtained by cooling to 80°C at 10°C/min. The dichroic ratio was then measured at each temperature while further cooling to 40°C at 10°C/min. The dichroic ratio at the temperature and wavelength that showed the maximum dichroic ratio was determined to be the dichroic ratio of the anisotropic dye film.

In the first invention, the dichroic ratio of the anisotropic dye film measured as described above is preferably 23 or more.
In the second invention, the dichroic ratio of the anisotropic dye film measured as described above is preferably 13 or more, and more preferably 20 or more.

[Light resistance evaluation]
From Az measured as described below, lightfastness was evaluated from the maximum Az maintenance rate (maximum Az after lightfastness test/maximum Az before lightfastness test×100) based on the maximum Az of the anisotropic dye film at 0 hours (before lightfastness test).

Specifically, the composition was injected into the sandwich cell in an isotropic phase, cooled to 40°C at 10°C/min, and then photopolymerized under a nitrogen atmosphere with a high pressure mercury lamp (500mJ/ ^cm2 ) to obtain a polymerized anisotropic dye film, and Tz was measured at 5 nm intervals in the wavelength range of 400 to 800 nm with the above spectrophotometer to obtain Az before the light resistance test. Furthermore, the film was placed in a weather resistance tester (manufactured by Atlas, product name "Atlas Weatherometer CI4000", black panel temperature 58.0°C, test chamber temperature 33.0°C, relative humidity 50%, irradiance 0.55W/ ^m2 (340nm), total exposure 79.2kJ/ ^m2 ) for 40 hours to perform a light resistance test. After the light resistance test, Tz was measured with the above spectrophotometer, and Az after the light resistance test was measured.
Az and Tz are as described above.

(Evaluation Criteria for Light Fastness Evaluation)
○: Maximum Az retention rate is 80% or more ×: Maximum Az retention rate is less than 80%

[Synthesis of polymerizable liquid crystal compound]
<Polymerizable Liquid Crystal Compound (I-1)>
A polymerizable liquid crystal compound (I-1) represented by the following structural formula was synthesized according to the description of JP2020-042305A, in which _C11H22 means that 11 _methylene chains are bonded in a linear manner.

The isotropic phase appearance temperature (phase transition temperature from liquid crystal to liquid and from liquid to liquid crystal) of the polymerizable liquid crystal compound (I-1) was determined by differential scanning calorimetry. For the differential scanning calorimetry, 0.2 parts by mass of 4-methoxyphenol was added as a polymerization inhibitor to 100 parts by mass of the polymerizable liquid crystal compound (I-1).
The phase transition temperature of this polymerizable liquid crystal compound (I-1) from liquid crystal to liquid was 111.0°C, and the phase transition temperature from liquid crystal to liquid crystal was 109.4°C.
It should be noted that it was confirmed by observation with a polarizing microscope and X-ray structural analysis that this temperature was the isotropic phase appearance temperature.

[Synthesis of dyes]
<Dye (II-1)>
Dye (II-1) was synthesized according to the synthesis method described below: Compound (II-1-a) was synthesized according to the method described in JP-A-2010-155924.

In a reactor, compound (II-1-a) (1.61 g, 5.0 mmol) was dissolved in N-methylpyrrolidone (30 mL) under a nitrogen atmosphere at room temperature, and then concentrated hydrochloric acid (2.1 mL, 4.2 eq.) was added and cooled to an internal temperature of 5°C. An aqueous solution of sodium nitrite (40% by mass, 0.40 g, 1.2 eq.) was added and stirred at an internal temperature of 0 to 5°C for 1.5 hours to obtain a diazonium salt solution. In a separate reactor, diethylaniline (1.49 g, 2.0 eq.) was dissolved in N-methylpyrrolidone (10 mL) under a nitrogen atmosphere at room temperature, and then cooled to an internal temperature of 0°C. The diazonium salt solution was added to this at an internal temperature of 0 to 5°C, and then sodium acetate (5.0 g, 12 eq.) was added and stirred for 1 hour while returning to room temperature. Purified water (40 mL) was added dropwise, and the precipitate was collected by suction filtration and washed with purified water (20 mL) to obtain a brown wet solid. This crude product was separated and purified by silica gel column chromatography (hexane/dichloromethane) and concentrated. The resulting yellow solid was dispersed in methanol (40 mL) and stirred at room temperature for 1 hour, after which the solid was collected by filtration to obtain 2.05 g of dye (II-1).

The structure of dye (II-1) was confirmed by nuclear magnetic resonance (NMR) spectroscopy, and the results are shown below.
^1H -NMR ( _CDCl3 , 400MHz) δ0.93 (t, 3H, J = 7.1Hz), δ1.10-1.18 (m, 2H), δ1.22-1.38 (m, 15H), δ1.46-1.56 (m, 2H), δ1.87-2.02 (m, 4H), δ2.50-2.60 (m, 1H), δ3.50 (q, 4H, J = 6.6Hz), δ6.77 (d, 2H, J = 8.7Hz), δ7.33 (d, 2H, J = 8.7Hz), δ7.61 (d, 2H, J = 8.4Hz), δ7.71 (d, 2H, J = 8.4Hz), δ7.87-7.97 (m, 4H)

<Dye (II-2)>
Dye (II-2) was synthesized according to the synthesis method described below.

In a reactor, compound (II-1-a) (0.64 g, 2.0 mmol) was dissolved in N-methylpyrrolidone (10 mL), and concentrated hydrochloric acid (0.84 mL, 5.0 eq.) was added and cooled to an internal temperature of 5°C. Next, sodium nitrite (0.145 g, 1.05 eq.) was dissolved in a small amount of water and added, and the mixture was stirred at an internal temperature of 0 to 5°C for 1.5 hours to obtain a diazonium salt solution. In a separate reactor, 1-phenylpyrrolidine (0.59 g, 2.0 eq.) was dissolved in methanol (10 mL) and cooled to an internal temperature of 0°C. The diazonium salt solution was added to this at an internal temperature of 0 to 5°C, and then sodium acetate (2.0 g, 12 eq.) was added and the mixture was stirred for 1 hour while returning to room temperature. Purified water was added dropwise, and the precipitate was collected by suction filtration and washed with purified water to obtain a brown wet solid. This crude product was separated, purified, and concentrated by silica gel column chromatography (toluene). The resulting yellow solid was dispersed in methanol and stirred at room temperature for 1 hour, after which the solid was filtered to obtain 0.49 g of dye (II-2).

<Dye (II-3)>
Dye (II-3) was synthesized according to the synthesis method described below.

In a reactor, compound (II-1-a) (0.64 g, 2.0 mmol) was dissolved in N-methylpyrrolidone (10 mL) under a nitrogen atmosphere at room temperature, and then concentrated hydrochloric acid (0.99 mL, 5.0 eq.) was added and cooled to an internal temperature of 5°C. An aqueous solution of sodium nitrite (40% by mass, 0.145 g, 1.05 eq.) was added, and the mixture was stirred at an internal temperature of 0 to 5°C for 1.5 hours, and then sulfamic acid (10% by mass, 0.3 mL) was added to obtain a diazonium salt solution. In another reactor, N-phenylpiperidine (0.645 g, 2.0 eq.) was dissolved in methanol (10 mL) under a nitrogen atmosphere at room temperature, and then cooled to an internal temperature of 0°C. The diazonium salt solution was added here at an internal temperature of 0 to 5°C, and then sodium acetate (2.0 g, 12 eq.) was added, and the mixture was stirred for 1 hour while being returned to room temperature. Purified water (40 mL) was added dropwise, and the precipitate was collected by suction filtration and washed with purified water (20 mL) to obtain a brown wet solid. This crude material was separated and purified by silica gel column chromatography (hexane/dichloromethane) and concentrated. The resulting yellow solid was dispersed in methanol (40 mL) and stirred at room temperature for 1 hour, after which the solid was collected by filtration to obtain 0.25 g of dye (II-3).

<Dye (II-4)>
Dye (II-4) was synthesized according to the synthesis method described below.

Synthesis of compound (II-4-a):
Acetic acid (500 mL) was added to compound (II-1-a) (15.0 g, 0.0467 mol) at room temperature under a nitrogen stream, and the mixture was stirred and dissolved at 35° C., and 1-nitroso-4-nitrobenzene (7.8 g, 1.1 eq.) was added in portions, and the mixture was stirred at room temperature overnight. The reaction solution was poured into 200 mL of purified water, stirred at room temperature for a while, filtered by suction, and rinsed with purified water (200 mL) and methanol (200 mL) to obtain 15.9 g of compound (II-4-a).

Synthesis of compound (II-4-b):
Compound (II-4-a) (15.9 g, 0.0348 mol) was added to 400 mL of ethanol at room temperature under a nitrogen stream, and the mixture was stirred to dissolve. NaS·H ₂ O (11.1 g, 1.9 eq.) was added, and the mixture was stirred at 78° C. for 2 hours. The reaction solution was poured into purified water (110 mL), stirred at room temperature for a while, filtered by suction, and rinsed with purified water (150 mL) and methanol (200 mL) to obtain 13.8 g of compound (II-4-b).

Synthesis of dye (II-4):
In a reactor, compound (II-4-b) (2.0 g, 4.70 mmol) was dissolved in N-methylpyrrolidone (50 mL) at room temperature, and then concentrated hydrochloric acid (1.37 mL, 3.8 eq.) was added and cooled to an internal temperature of 5° C. Sodium nitrite (0.356 g, 1.1 eq.) was dissolved in a small amount of water and added dropwise, and the mixture was stirred at an internal temperature of 0 to 5° C. for 1 hour to obtain a diazonium salt solution. In another reactor, diethylaniline (1.05 g, 1.5 eq.) and sulfamic acid (0.138 g, 1.4 mmol) were dissolved in methanol (50 mL) at room temperature under a nitrogen atmosphere, and the mixture was cooled to an internal temperature of 5° C. The diazonium salt solution was added thereto at an internal temperature of 0 to 5° C., and the mixture was stirred for 4 hours at an internal temperature of 0 to 5° C. for 1 hour while returning to room temperature. Sodium acetate (0.85 g, 14 mmol) was added and the mixture was stirred at room temperature for 1 hour. Purified water (100 mL) was added dropwise, and the precipitate was collected by suction filtration and washed with purified water (100 mL) to obtain a brown wet solid. This crude product was separated and purified by silica gel column chromatography (hexane/dichloromethane) to obtain 0.55 g of dye (II-4).

The maximum absorption wavelength (λ _max1 ) of dye (II-4) in a 10 ppm chloroform solution was 495 nm.

The structure of dye (II-4) was confirmed by NMR spectrum measurement, and the results are shown below.
^1H -NMR ( _CDCl3 , 400MHz) δ 0.91 (t, 3H, J=6.9Hz), δ1.01-1.16(m,2H), δ1.24-1.35(m,14H), δ1.44-1.51(m,2H), δ1.89-1.96(m,4H), δ2.50-2.60(m,1H), δ3.45-3.52(m,4H), δ6.73-6.75(m,2H), δ7.33(d,2H,J=8.2Hz), δ7.61(d,2H,J=8.2Hz), δ7.77(d,2H,J=8.8Hz), δ7.90(d,2H,J=8.8Hz), δ7.90-8.10(m,6H)

<Dye (II-5)>
Dye (II-5) was synthesized according to the synthesis method described below.

Synthesis of compound (II-5-a):
N-Ethylaniline (130.0 g, 1073 mmol), 2-iodopropane (200 g, 1080 mmol), potassium carbonate (297 g, 2146 mmol), and acetonitrile (520 mL) were mixed and heated and stirred under reflux for 16 hours. After cooling to 25°C, the reaction solution was filtered, and the filtrate was concentrated. The resulting yellow oily crude product was purified by silica gel chromatography (hexane/dichloromethane) to obtain 100 g of compound (II-5-a).

Synthesis of dye (II-5):
In a reactor, under a nitrogen atmosphere at room temperature, compound (II-4-b) (1.1 g, 2.58 mmol) was dissolved in N-methylpyrrolidone (20 mL), and then concentrated hydrochloric acid (0.75 g, 3.5 eq.) was added and cooled to an internal temperature of 5° C. Sodium nitrite (0.20 mg, 1.1 eq.) was added dropwise, and the mixture was stirred at an internal temperature of 0 to 5° C. for 1 hour to obtain a diazonium salt solution. In another reactor, under a nitrogen atmosphere at room temperature, compound (II-5-a) (0.842 g, 2.0 eq.), sulfamic acid (1.0 g, 10.5 mmol) were dissolved in methanol (12 mL) and tetrahydrofuran (2 mL), and then cooled to an internal temperature of 0° C. The diazonium salt solution was added thereto over 20 minutes at an internal temperature of 0 to 5° C., and stirring was continued for 4 hours at an internal temperature of 0 to 5° C., and for 1 hour while returning to room temperature. Sodium acetate (0.85 g, 14 mmol) was added and stirred at room temperature for 1 hour. Purified water (20 mL) was added dropwise, and the precipitate was collected by suction filtration and washed with purified water (20 mL) to obtain a brown wet solid. This crude product was separated and purified by silica gel column chromatography (hexane/dichloromethane) to obtain 0.30 g of dye (II-5).

The maximum absorption wavelength (λ _max1 ) of dye (II-5) in a 10 ppm chloroform solution was 497 nm.

The structure of dye (II-5) was confirmed by NMR spectrum measurement, and the results are shown below.
^1H -NMR ( _CDCl3 , 400MHz) δ0.90-0.96 (m, 3H), δ1.02-1.17 (m, 2H), δ1.18-1.42 (m, 17H), δ1.46-1.59 (m, 1H), δ1.88-2.02 (m, 4H), δ2.52-2.59 (m, 1H), δ3.40-3.45 (m, 2H), δ4.21-4.35 (m, 1H), δ6.83-6.86 (m, 2H), δ7.35 (d, 2H, J=8.2Hz), δ7.64 (d, 2H, J=8.2Hz), δ7.77 (d, 2H, J=8.8Hz), δ7.90-8.10 (m, 8H).

<Dye (II-6)>
Dye (II-6) was synthesized according to the synthesis method described below.

Synthesis of compound (II-6-a):
In a reactor, N-methylaniline (50 g, 0.47 mol) was dissolved in acetonitrile (200 mL) at room temperature under a nitrogen atmosphere, and then 2-iodopropane (87 g, 1.1 eq) and potassium carbonate (129 g, 2.0 eq) were added, and the mixture was stirred for 14 hours under heating and reflux at an external temperature of 80° C. After cooling to 25° C., the reaction solution was filtered, and the filtrate was concentrated. The resulting yellow oily crude product was purified by silica gel chromatography (hexane/dichloromethane) to obtain 39 g of compound (II-6-a).

Synthesis of dye (II-6):
In a reactor, under a nitrogen atmosphere at room temperature, compound (II-4-b) (433 mg, 2 mmol) was dissolved in N-methylpyrrolidone (8 mL), and then concentrated hydrochloric acid (319 mg, 3.0 eq.) was added and cooled to an internal temperature of 5 ° C. An aqueous solution of sodium nitrite (20 mass%, 397 mg, 1.2 eq.) was added dropwise, and the mixture was stirred at an internal temperature of 0 to 5 ° C. for 1 hour to obtain a diazonium salt solution. In another reactor, under a nitrogen atmosphere at room temperature, compound (II-6-a) (314 mg, 2.0 eq.) was dissolved in methanol (8 mL) and tetrahydrofuran (1 mL), and the mixture was cooled to an internal temperature of 0 ° C. The diazonium salt solution was added thereto over 20 minutes at an internal temperature of 0 to 5 ° C., and the mixture was stirred for 4 hours at an internal temperature of 0 to 5 ° C. for 1 hour while returning to room temperature. Purified water (5 mL) was added dropwise, and the precipitate was collected by suction filtration, and washed with purified water (5 mL) to obtain a brown wet solid. This crude product was separated and purified by silica gel column chromatography (hexane/dichloromethane) to obtain 101 mg of dye (II-6).

The maximum absorption wavelength (λ _max1 ) of dye (II-6) in a 10 ppm chloroform solution was 491 nm.
The structure of dye (II-6) was confirmed by NMR spectrum measurement, and the results are shown below.
^1H -NMR ( _CDCl3 , 400MHz) δ0.93 (t, 3H, J = 6.9Hz), δ1.02-1.17 (m, 2H), δ1.18-1.42 (m, 16H), δ1.46-1.59 (m, 1H), δ1.88-2.02 (m, 4H), δ2.50-2.60 (m, 1H), δ2.92 (s, 3H), δ4.21-4.35 (m, 1H), δ6.83-6.95 (m, 2H), δ7.35 (d, 2H, J = 8.2Hz), δ7.64 (d, 2H, J = 8.2Hz), δ7.77 (d, 2H, J = 8.8Hz), δ7.90-8.10 (m, 8H)

<Dye (II-7)>
Dye (II-7) was synthesized according to the synthesis method described below.

Synthesis of compound (II-7-a):
In a reactor, N-isopropylaniline (19.0 g, 0.140 mol) was dissolved in N,N-dimethylformamide (76 mL) at room temperature under a nitrogen atmosphere, and then 1-fluoro-2-iodoethane (24.4 g, 1.1 eq) and potassium carbonate (38.8 g, 2.0 eq) were added, and the mixture was stirred for 15 hours under heating and reflux at an external temperature of 95° C. After cooling to 25° C., the reaction solution was filtered, and the filtrate was concentrated. The resulting yellow oily crude product was purified by silica gel chromatography (hexane/dichloromethane) to obtain 7.91 g of compound (II-7-a).

Synthesis of dye (II-7):
In a reactor, under a nitrogen atmosphere at room temperature, compound (II-4-b) (1.74 mg, 2.35 mmol) was dissolved in N-methylpyrrolidone (100 mL), and concentrated hydrochloric acid (1.18 mL, 3.5 eq.) was added and cooled to an internal temperature of 5° C. Sodium nitrite (0.31 g, 1.1 eq.) was dissolved in a small amount of water, and then added dropwise, and stirred at an internal temperature of 0 to 5° C. for 1 hour to obtain a diazonium salt solution. In another reactor, under a nitrogen atmosphere at room temperature, compound (II-7-a) (1.48 g, 2.0 eq.) was dissolved in methanol (17 mL), and then cooled to an internal temperature of 0° C. The diazonium salt solution was added thereto at an internal temperature of 0 to 5° C. and stirred at an internal temperature of 0 to 5° C. for 1 hour, and then sodium acetate (0.75 g) was added and stirred for 1 hour while returning to room temperature. Purified water (20 mL) was added dropwise, and the precipitate was collected by suction filtration and washed with purified water (50 mL) and methanol (200 mL) to obtain a brown wet solid. This crude product was separated and purified by silica gel column chromatography (hexane/dichloromethane) to obtain 0.274 g of dye (II-7).

The maximum absorption wavelength (λ _max1 ) of dye (II-7) in a 10 ppm chloroform solution was 470 nm.
The structure of dye (II-7) was confirmed by NMR spectrum measurement, and the results are shown below.
^1H -NMR ( _CDCl3 , 400MHz) δ 0.90-0.95 (m, 3H), δ 1.02-1.17 (m, 2H), δ 1.18-1.42 (m, 14H), δ 1.46-1.59 (m, 1H), δ 1.88-2.02 (m, 4H), δ 2.52-2.59 (m, 1H), δ 3.65-3.75 (m, 2H) , δ 4.21-4.30 (m, 1H), δ 6.54-6.60 (m, 1H), δ 6.66-6.70 (m, 1H), δ 7.35 (d, 2H, J = 8.2 Hz), δ 7.64 (d, 2H, J = 8.2 Hz), δ 7.77 (d, 2H, J = 8.8 Hz), δ 7.90-8.10 (m, 8H)

<Dye (II-8)>
Dye (II-8) was synthesized according to the synthesis method described below.

Synthesis of compound (II-8-a):
3,5,5-Triethyl-1-hexanol (76.8 g, 532 mmol), 47% aqueous hydrogen bromide (HBr) solution (100.8 g, 586 mmol), and concentrated sulfuric acid (16.6 g, 185 mmol) were mixed and stirred at 120° C. for 5 hours. After cooling to 25° C., the mixture was added to hexane (1200 mL) and washed with purified water (2400 mL x 3 times). The organic layer was concentrated and then purified by silica gel chromatography (hexane) to obtain 71.0 g of compound (II-8-a).

Synthesis of compound (II-8-b):
Under a nitrogen stream, 4-nitrophenol (65.0 g, 467 mmol), compound (II-8-a) (116.2 g, 560 mmol), dimethylformamide (520 mL), and potassium carbonate (129.1 g, 934 mmol) were mixed and stirred at 90° C. for 6 hours. Purified water (1000 mL) was added thereto, and the mixture was extracted with a 1/4 mixture of ethyl acetate and hexane, and the oil layer was concentrated. The mixture was purified by silica gel chromatography (ethyl acetate/hexane), and 113.5 g of compound (II-8-b) was obtained.

Synthesis of compound (II-8-c):
Compound (II-8-b) (113.5 g, 427.7 mmol) and ethyl acetate (1100 mL) were mixed under an argon stream, and then palladium carbon (5% Pd/C, water content 55% by mass, 11.4 g) was added and stirred under a hydrogen atmosphere at 25° C. for 60 hours. The atmosphere in the vessel was replaced with argon, and the catalyst was filtered off. The catalyst was extracted with dichloromethane, and the organic layers were combined and concentrated, and then purified by silica gel chromatography (dichloromethane) to obtain 99.5 g of compound (II-8-c).

Synthesis of compound (II-8-d):
Compound (II-8-c) (43.3 g, 0.184 mol) and acetic acid (1.3 L) were added at room temperature under a nitrogen stream, stirred to dissolve, and 1-nitroso-4-nitrobenzene (28.0 g, 1.0 eq.) was added in portions. After stirring for 4 hours, 1-nitroso-4-nitrobenzene (8.4 g, 0.3 eq.) was added, and stirring was continued at room temperature overnight. Dichloromethane (3.9 L) and purified water (1.3 L) were poured, and after stirring for a while, oil and water were separated. The aqueous layer was extracted with dichloromethane (1.3 L), combined with the original organic layer, washed successively with purified water (1.3 L), saturated sodium bicarbonate water (1.3 L), and saturated saline (500 mL), dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated to obtain a reddish brown solid. This crude product was purified by silica gel column chromatography (hexane/dichloromethane=3/1) to obtain 52.08 g of compound (II-8-d).

Synthesis of compound (II-8-e):
Compound (II-8-d) (52.0 g, 0.141 mol), ethanol (520 mL), purified water (52 mL), and sodium sulfide pentahydrate (Na ₂ S.5H ₂ O) (47.4 g, 2.0 eq.) were added and stirred at an external temperature of 80° C. for 6 hours. After cooling to room temperature, the reaction solution was poured into purified water (500 mL) and stirred for a while, then filtered by suction and rinsed with purified water (250 mL). The obtained solid was purified by silica gel column chromatography (dichloromethane) to obtain 34.40 g of compound (II-8-e).

Synthesis of compound (II-8-f):
Compound (II-8-e) (34.4 g, 0.101 mol) and acetic acid (1.0 L) were added at room temperature under a nitrogen stream and stirred to dissolve, and 1-nitroso-4-nitrobenzene (20.0 g, 1.3 eq.) was added in portions and stirred at room temperature overnight. The reaction solution was poured into purified water, stirred at room temperature for a while, filtered by suction, and rinsed with purified water. This solid was purified by silica gel column chromatography (chloroform) to obtain 38.6 g of compound (II-8-f).

Synthesis of compound (II-8-g):
Compound (II-8-f) (38.6 g, 81.5 mmol), ethanol (386 mL), purified water (39 mL) and Na ₂ S.5H ₂ O (27.4 g, 2.0 eq.) were added at room temperature under a nitrogen atmosphere, and the mixture was stirred at an external temperature of 80° C. for 6 hours. After cooling to room temperature, the reaction solution was poured into purified water (400 mL) and stirred for a while, then filtered by suction and rinsed with purified water (200 mL). The obtained solid was purified by silica gel column chromatography (hexane/dichloromethane=1/1) to obtain 30.20 g of compound (II-8-g).

Synthesis of dye (II-8):
Compound (II-8-g) (1.5 g, 3.38 mmol) and HCl (1.4 mL) were dissolved in N-methyl-2-pyrrolidone (NMP) (20 mL) and cooled to an internal temperature of 0° C. Sodium nitrate (0.256 g, 3.718 mmol) was dissolved in 5 mL of purified water and added dropwise to the previous solution at an internal temperature of 0 to 3° C. and stirred at an internal temperature of 0 to 2° C. for 1 hour. In another reactor, 2-[ethyl(phenyl)amino]acetic acid (1.05 g, 1.5 eq.) was dissolved in methanol (10 mL) at room temperature under a nitrogen atmosphere, and then sodium acetate (1.44 g) was added and cooled to an internal temperature of 0° C. The previous diazonium salt solution was added thereto over 30 minutes at an internal temperature of 0 to 5° C., and stirred for 1 hour at an internal temperature of 0 to 5° C. and for 2 hours while returning to room temperature. Purified water was added, and the mixture was filtered and washed with methanol. The resulting crude product was purified by silica gel column chromatography (toluene/dichloromethane=1/3) to obtain 0.24 g of dye (II-8).

The maximum absorption wavelength (λ _max1 ) of dye (II-8) in a 10 ppm chloroform solution was 491 nm.
The structure was also confirmed by NMR spectroscopy, and the results are shown below.
^1H -NMR ( _CDCl3 , 400MHz) δ0.92 (s, 9H), δ1.02 (d, 3H, J = 6.8Hz), δ1.12-1.34 (m, 5H), δ1.66-1.85 (m, 3H), δ3.54 (q, 2H, J = 6.8Hz), δ3.698 (q, 2H, J = 8.8Hz), δ4.09 (t, 2H, J = 6.8Hz), δ4.31 (t, 2H, J = 6.8Hz), δ6.83 (d, 2H, J = 9.2Hz), δ7.03 (d, 2H, J = 9.2Hz), δ7.92-8.10 (m, 12H)

<Dye (III-1)>
Dye (III-1) was synthesized according to the synthesis method described below.

Synthesis of compound (III-1-a):
A mixed solution of 4-iodoaniline (10 mmol, 2.2 g) in 2N HCl aqueous solution (15 mL) and ethanol (30 mL) was cooled to 0°C, and then an aqueous solution (10 mL) of sodium nitrite (11 mmol, 0.76 g) was added dropwise little by little, and the mixture was stirred at 0°C for 10 minutes. After that, amidosulfuric acid (0.2 mmol) was added to the reaction solution, and the mixture was further stirred at 0°C for 10 minutes to obtain a diazonium salt solution. Meanwhile, a mixed solution of N,N-diethylaniline (10 mmol, 1.49 g) and sodium acetate (20 mmol, 1.7 g) in ethanol (200 mL) and water (100 mL) was cooled to 0°C, and the diazonium salt solution was added little by little, and the mixture was stirred while being heated to room temperature. NaOH was added to the obtained reaction solution to adjust the pH to 10-12. The crude product was filtered, washed with water, dried, and recrystallized from methanol to obtain 2.78 g of compound (III-1-a).

Synthesis of dye (III-1):
Under a nitrogen atmosphere, triethylamine (30 mL), 4-butylphenylacetylene (2.5 mmol, 332 mg), and PdCl ₂ (PPh ₃ ) 2 (0.1 mmol, 70 mg) were added to a solution of compound (III-1-a) (2 mmol, 758 mg) and CuI (0.3 mmol, 57 mg) in tetrahydrofuran (30 mL), and the mixture was heated under reflux for 6 hours. The precipitate was filtered and then concentrated under reduced pressure. The obtained crude product was suspended and washed in methanol, and purified by silica gel chromatography (developing solution (hexane:ethyl acetate=9:1 (volume ratio)) to obtain 836 mg of dye (III-1).

The chemical structures of the polymerizable liquid crystal compound (I-1) and dyes (II-1), (II-2), (II-3), (II-4), (II-5), (II-6), (II-7) and (II-8) synthesized above, as well as the comparative dyes (III-1) and (III-2), are shown below.
The maximum absorption wavelength (λ _max1 ) of this dye (III-2) in a 10 ppm chloroform solution was 454 nm.

[Examples of the first invention and comparative examples]
[Example 1]
20.05 parts of the polymerizable liquid crystal compound (I-1) and 0.40 parts of the dye (II-1) were added to 4016.05 parts of chloroform, and the mixture was stirred to dissolve, and then the solvent was removed to obtain a composition 1A. The r _n1 /r _n2 ratio of the composition 1A was 0.75.
It was confirmed that Composition 1A exhibited liquid crystallinity by observing birefringence at 40° C. using a polarizing microscope equipped with a hot stage.
In order to determine the dichroic ratio by the above-mentioned method, an anisotropic dye film 1A was prepared using the obtained composition 1A in a sandwich cell having a cell gap of 8.0 μm, and the dichroic ratio of the anisotropic dye film 1A was determined.
Furthermore, 24.15 parts of the polymerizable liquid crystal compound (I-1), 0.48 parts of the dye (II-1), 0.48 parts of a polymerization initiator (Irgacure 369 manufactured by IGM Resins B.V.), and 0.36 parts of a surfactant (BYK-361N manufactured by BYK) were added to 6013.38 parts of chloroform, and the mixture was stirred to dissolve, and then the solvent was removed to obtain composition 1B.
In order to determine the light resistance by the above-mentioned method, an anisotropic dye film 1B was prepared using the obtained composition 1B in a sandwich cell having a cell gap of 8.0 μm, and the light resistance of the anisotropic dye film 1B was determined.
The evaluation results of the dichroic ratio and the light fastness are shown in Table 1.

[Example 2]
Except for adding 0.39 parts of dye (II-2) instead of 0.40 parts of dye (II-1), composition 2A and anisotropic dye film 2A were obtained in the same manner as composition 1A and anisotropic dye film 1A in Example 1. r _n1 /r _n2 of composition 2A was 0.75.
It was confirmed that Composition 2A exhibited liquid crystallinity by observing birefringence at 40° C. using a polarizing microscope equipped with a hot stage.
The dichroic ratio of the anisotropic dye film 2A was also determined.
Composition 2B and anisotropic dye film 2B were obtained in the same manner as composition 1B and anisotropic dye film 1B in Example 1, except that 0.48 parts of dye (II-2) was added instead of 0.48 parts of dye (II-1).
The light resistance of the anisotropic dye film 2B was also determined.
The evaluation results of the dichroic ratio and the light fastness are shown in Table 1.

[Example 3]
Except for adding 0.50 parts of dye (II-3) instead of 0.40 parts of dye (II-1), composition 3A and anisotropic dye film 3A were obtained in the same manner as composition 1A and anisotropic dye film 1A in Example 1. r _n1 /r _n2 of composition 3A was 0.75.
It was confirmed that Composition 3A exhibited liquid crystallinity by observing birefringence at 40° C. using a polarizing microscope equipped with a hot stage.
The dichroic ratio of the anisotropic dye film 3A was also determined.
Composition 3B and anisotropic dye film 3B were obtained in the same manner as composition 1B and anisotropic dye film 1B in Example 1, except that 0.61 parts of dye (II-3) was added instead of 0.48 parts of dye (II-1).
In the same manner as in Example 1, the light resistance of the anisotropic dye film 3B was determined.
The evaluation results of the dichroic ratio and the light fastness are shown in Table 1.

[Example 4]
Except for adding 0.39 parts of dye (II-4) instead of 0.40 parts of dye (II-1), composition 4 and anisotropic dye film 4A were obtained in the same manner as composition 1A and anisotropic dye film 1A in Example 1. r _n1 /r _n2 of composition 4A was 0.6.
It was confirmed that Composition 4A exhibited liquid crystallinity by observing birefringence at 40° C. using a polarizing microscope equipped with a hot stage.
The dichroic ratio of the anisotropic dye film 4A was also determined.
Composition 4B and anisotropic dye film 4B were obtained in the same manner as composition 1B and anisotropic dye film 1B in Example 1, except that 0.47 part of dye (II-4) was added instead of 0.48 part of dye (II-1).
The light resistance of the anisotropic dye film 4B was also determined.
The evaluation results of the dichroic ratio and the light fastness are shown in Table 1.

[Example 5]
Except for adding 0.39 parts of dye (II-5) instead of 0.40 parts of dye (II-1), composition 5A and anisotropic dye film 5A were obtained in the same manner as composition 1A and anisotropic dye film 1A in Example 1. r _n1 /r _n2 of composition 5A was 0.6.
It was confirmed that Composition 5A exhibited liquid crystallinity by observing birefringence at 40° C. using a polarizing microscope equipped with a hot stage.
The dichroic ratio of the anisotropic dye film 5A was also determined.
Composition 5B and anisotropic dye film 5B were obtained in the same manner as composition 1B and anisotropic dye film 1B in Example 1, except that 0.48 parts of dye (II-1) was replaced with 0.48 parts of dye (II-5).
The light resistance of the anisotropic dye film 5B was also determined.
The evaluation results of the dichroic ratio and the light fastness are shown in Table 1.

[Example 6]
Except for adding 0.40 parts of dye (II-6) instead of 0.40 parts of dye (II-1), composition 6A and anisotropic dye film 6A were obtained in the same manner as composition 1A and anisotropic dye film 1A in Example 1. r _n1 /r _n2 of composition 6A was 0.6.
It was confirmed that Composition 6A exhibited liquid crystallinity by observing birefringence at 40° C. using a polarizing microscope equipped with a hot stage.
The dichroic ratio of the anisotropic dye film 6A was also determined.
Composition 6B and anisotropic dye film 6B were obtained in the same manner as composition 1B and anisotropic dye film 1B in Example 1, except that 0.48 parts of dye (II-1) was replaced with 0.48 parts of dye (II-6).
The light resistance of the anisotropic dye film 6B was also determined.
The evaluation results of the dichroic ratio and the light fastness are shown in Table 1.

[Example 7]
Except for adding 0.42 parts of dye (II-7) instead of 0.40 parts of dye (II-1), composition 7A and anisotropic dye film 7A were obtained in the same manner as composition 1A and anisotropic dye film 1A in Example 1. r _n1 /r _n2 of composition 7A was 0.6.
It was confirmed that Composition 7A exhibited liquid crystallinity by observing birefringence at 40° C. using a polarizing microscope equipped with a hot stage.
The dichroic ratio of the anisotropic dye film 7A was also determined.
Composition 7B and anisotropic dye film 7B were obtained in the same manner as composition 1B and anisotropic dye film 1B in Example 1, except that 0.52 parts of dye (II-7) was added instead of 0.48 parts of dye (II-1).
The light resistance of the anisotropic dye film 7B was also determined.
The evaluation results of the dichroic ratio and the light fastness are shown in Table 1.

[Comparative Example 1]
Composition 8A and anisotropic dye film 8A were obtained in the same manner as composition 1A and anisotropic dye film 1A in Example 1, except that 0.35 parts of dye (III-1) was used instead of _0.40 parts of dye ( _II -1).
It was confirmed that Composition 8A exhibited liquid crystallinity by observing birefringence at 40° C. using a polarizing microscope equipped with a hot stage.
The dichroic ratio of the anisotropic dye film 8A was also determined.
Composition 8B and anisotropic dye film 8B were obtained in the same manner as composition 1B and anisotropic dye film 1B in Example 1, except that 0.42 parts of dye (III-1) was added instead of 0.48 parts of dye (II-1).
The light resistance of the anisotropic dye film 8B was also determined.
The evaluation results of the dichroic ratio and the light fastness are shown in Table 1.

As is clear from Table 2, in Examples 1 to 7 in which the compound of the first invention was used, the maximum dichroic ratio was high and the light resistance was also good.
On the other hand, in Comparative Example 1, the dichroic ratio and light fastness were lower than those in the Examples.

[Examples of the second invention and comparative examples]
[Example 8]
20.05 parts of the polymerizable liquid crystal compound (I-1) and 0.39 parts of the dye (II-4) were added to 4016.05 parts of chloroform, and the mixture was stirred to dissolve, and then the solvent was removed to obtain a composition 9A. The r _n1 /r _n2 ratio of the composition 9A was 0.6.
It was confirmed that Composition 9A exhibited liquid crystallinity by observing birefringence at 40° C. using a polarizing microscope equipped with a hot stage.
In order to determine the dichroic ratio by the above-mentioned method using the obtained composition 9A, an anisotropic dye film 9A was prepared using a sandwich cell with a cell gap of 8.0 μm, and the wavelength (λ _max2 ) at which the dichroic ratio and orthogonal absorbance of the anisotropic dye film 8A were maximized was determined.
Furthermore, 24.15 parts of the polymerizable liquid crystal compound (I-1), 0.47 parts of the dye (II-4), 0.48 parts of a polymerization initiator (Irgacure 369 manufactured by IGM Resins B.V.), and 0.36 parts of a surfactant (BYK-361N manufactured by BYK) were added to 6013.38 parts of chloroform, and the mixture was stirred to dissolve, and then the solvent was removed to obtain composition 9B.
In order to determine the light resistance of the obtained composition 9B by the above-mentioned method, an anisotropic dye film 9B was prepared using a sandwich cell having a cell gap of 8.0 μm, and the light resistance of the anisotropic dye film 9B was determined.
The evaluation results of the dichroic ratio and light fastness are shown in Table 3 together with the values of λ _max1 , λ _max2 and λ _max2 - λ _max1 of dye (II-4).

[Example 9]
A composition 10A and an anisotropic dye film 10A were obtained in the same manner as in the composition 9A and anisotropic dye film 9A of Example 8, except that 0.39 parts of dye (II-5) was added instead of 0.39 parts of dye (II-4). The r _n1 /r _n2 of the composition 10A was 0.6.
It was confirmed that Composition 10A exhibited liquid crystallinity by observing birefringence at 40° C. using a polarizing microscope equipped with a hot stage.
In addition, the dichroic ratio and the wavelength (λ _max2 ) at which the orthogonal absorbance of the anisotropic dye film 10A is maximized were determined.
Composition 10B and anisotropic dye film 10B were obtained in the same manner as composition 9B and anisotropic dye film 9B in Example 8, except that 0.48 parts of dye (II-5) was added instead of 0.48 parts of dye (II-4), and the light resistance of anisotropic dye film 10B was determined.
The evaluation results of the dichroic ratio and light fastness are shown in Table 3 together with the values of λ _max1 , λ _max2 and λ _max2 - λ _max1 of dye (II-5).

[Example 10]
Composition 11A and anisotropic dye film 11A were obtained in the same manner as composition 9A and anisotropic dye film 9A in Example 8, except that 0.40 parts of dye (II-6) was added instead of 0.39 parts of dye (II-4). r _n1 /r _n2 of composition 11A was 0.6.
It was confirmed that Composition 11A exhibited liquid crystallinity by observing birefringence at 40° C. using a polarizing microscope equipped with a hot stage.
In addition, the dichroic ratio and the wavelength (λ _max2 ) at which the orthogonal absorbance of the anisotropic dye film 11A is maximized were determined.
Composition 11B and anisotropic dye film 11B were obtained in the same manner as in Composition 9B and Anisotropic Dye Film 9B in Example 8, except that 0.48 parts of dye (II-4) was replaced with 0.48 parts of dye (II-6). The light resistance of the anisotropic dye film 11B was determined.
The evaluation results of the dichroic ratio and light fastness are shown in Table 3 together with the values of λ _max1 , λ _max2 and λ _max2 - λ _max1 of dye (II-6).

[Example 11]
Composition 12A and anisotropic dye film 12A were obtained in the same manner as composition 9A and anisotropic dye film 9A in Example 8, except that 0.42 parts of dye (II-7) was added instead of 0.39 parts of dye (II-4). r _n1 /r _n2 of composition 12A was 0.6.
It was confirmed that Composition 12A exhibited liquid crystallinity by observing birefringence at 40° C. using a polarizing microscope equipped with a hot stage.
In addition, the dichroic ratio and the wavelength (λ _max2 ) at which the orthogonal absorbance of the anisotropic dye film 12A is maximized were determined.
Composition 12B and anisotropic dye film 12B were obtained in the same manner as in composition 9B and anisotropic dye film 9B of Example 8, except that 0.52 parts of dye (II-7) was added instead of 0.48 parts of dye (II-4). The light resistance of anisotropic dye film 12B was determined.
The evaluation results of the dichroic ratio and lightfastness are shown in Table 3 together with the values of λ _max1 , λ _max2 and λ _max2 - λ _max1 of dye (II-7).

[Example 12]
Composition 13A and anisotropic dye film 13A were obtained in the same manner as composition 9A and anisotropic dye film 9A in Example 8, except that 0.27 parts of dye (II-8) was added instead of 0.39 parts of dye (II-4). r _n1 /r _n2 of composition 13A was 0.75.
It was confirmed that Composition 13A exhibited liquid crystallinity by observing birefringence at 40° C. using a polarizing microscope equipped with a hot stage.
Further, the dichroic ratio of the anisotropic dye film 13A and the wavelength (λ _max2 ) at which the orthogonal absorbance is maximized were determined.
Composition 13B and anisotropic dye film 13B were obtained in the same manner as composition 9B and anisotropic dye film 9B in Example 8, except that 0.39 parts of dye (II-8) was added instead of 0.48 parts of dye (II-4), and the light resistance of anisotropic dye film 13B was determined.
The evaluation results of the dichroic ratio and light fastness are shown in Table 3 together with the values of λ _max1 , λ _max2 and λ _max2 - λ _max1 of dye (II-8).

[Comparative Example 2]
Composition 14A and anisotropic dye film 14A were obtained in the same manner as composition 9A and anisotropic dye film 9A in Example 8, except that 0.55 parts of dye (III-2) was used instead of 0.39 parts of dye (II-4). r _n1 /r _n2 of composition 14A was 0.6.
It was confirmed that Composition 14A exhibited liquid crystallinity by observing birefringence at 40° C. using a polarizing microscope equipped with a hot stage.
In addition, the dichroic ratio and the wavelength (λ _max2 ) at which the orthogonal absorbance of the anisotropic dye film 14A is maximized were determined.
Composition 14B and anisotropic dye film 14B were obtained in the same manner as composition 9B and anisotropic dye film 9B in Example 8, except that 0.66 parts of dye (III-2) was added instead of 0.48 parts of dye (II-4), and the light resistance of anisotropic dye film 14B was determined.
The evaluation results of the dichroic ratio and light fastness are shown in Table 3 together with the values of λ _max1 , λ _max2 and λ _max2 - λ _max1 of dye (III-2).

As can be seen from Table 3, the dyes in the compositions used in Examples 8 to 12 satisfied λ _max2 - λ _max1 < 0, the anisotropic dye films showed high maximum dichroic ratios, and good lightfastness. On the other hand, the dyes in the composition used in Comparative Example 2 did not satisfy λ _max2 - λ _max1 < 0, and the anisotropic dye films showed lower maximum dichroic ratios and lightfastness than the examples.

Although the present invention has been described in detail using specific embodiments, it will be apparent to those skilled in the art that various modifications are possible within the scope of the invention.
This application is based on Japanese Patent Application No. 2022-160390 and Japanese Patent Application No. 2022-160391 filed on October 4, 2022, and is incorporated by reference in its entirety.

Claims

A compound represented by the following formula (1):

(In formula (1),
-XA represents a monovalent organic group.
-RA1 and -RA2 each independently represent an alkyl group which may have a substituent. -RA1 and -RA2 may be joined together to form a ring, but the -RA1 and -RA2 portions of the ring formed by -RA1 and -RA2 are formed only by a hydrocarbon chain.
-A 1 -, -A 2 -, -A 3 - and -A 4 - each independently represent a 1,4-phenylene group which may have a substituent.
n represents 0, 1, or 2.
When n is 2, multiple -A 3 - may be the same or different.
The compound according to claim 1, wherein -XA in the formula (1) is a hydrogen atom, -Ra, -O-Ra, -NH-Ra, -C(=O)-Ra, -C(=O)-O-Ra, -C(=O)-NH-Ra, -C(=O)-N(-Rb)-Ra, -O-C(=O)-Ra, -NH-C(=O)-Ra, -N(-Rb)-C(=O)-Ra, or -S-Ra (-Ra and -Rb each independently represent an alkyl group having 1 to 15 carbon atoms, which may have a branch, a cycloalkyl group having 5 to 14 atoms constituting a ring, or an aryl group having 5 to 14 atoms constituting a ring, and the alkyl group, cycloalkyl group, and aryl group each may have a substituent. Also, -Ra and -Rb may together form a ring having 2 to 15 carbon atoms, and the ring may have a substituent).
3. The compound according to claim 1, wherein -RA 1 and -RA 2 in the formula (1) each independently represent an alkyl group having 1 to 10 carbon atoms which may have a substituent.
A composition comprising a compound represented by the following formula (2) and a polymerizable liquid crystal compound:

(In formula (2),
-XB represents a monovalent organic group.
Each of -RB1 and -RB2 independently represents an alkyl group which may have a substituent, and -RB1 and -RB2 may combine together to form a ring.
-B 1 - and -B 2 - each independently represents a 1,4-phenylene group which may have a substituent.
Each of -B 3 - and -B 4 - independently represents a divalent aromatic hydrocarbon ring group which may have a substituent.
n represents 0, 1, or 2.
When n is 2, multiple -B 3 - may be the same or different.
5. The composition according to claim 4, wherein -B 4 - in the formula (2) is a 1,4-phenylene group which may have a substituent.
5. The composition according to claim 4, wherein -B 3 - in the formula (2) is a 1,4-phenylene group which may have a substituent.
The composition according to claim 4, wherein -XB in the formula (2) is a hydrogen atom, -Ra, -O-Ra, -NH-Ra, -C(=O)-Ra, -C(=O)-O-Ra, -C(=O)-NH-Ra, -C(=O)-N(-Rb)-Ra, -O-C(=O)-Ra, -NH-C(=O)-Ra, -N(-Rb)-C(=O)-Ra, or -S-Ra (-Ra and -Rb each independently represent an alkyl group having 1 to 15 carbon atoms, which may be branched, a cycloalkyl group having 5 to 14 atoms constituting a ring, or an aryl group having 5 to 14 atoms constituting a ring, and the alkyl group, cycloalkyl group, and aryl group each may have a substituent. Also, -Ra and -Rb may together form a ring having 2 to 15 carbon atoms, and the ring may have a substituent).
5. The composition according to claim 4, wherein --RB1 and --RB2 in formula (2) each independently represent an alkyl group having 1 to 10 carbon atoms which may have a substituent.
An anisotropic dye film formed using the composition according to any one of claims 4 to 8.
An optical element having the anisotropic dye film according to claim 9.
A composition comprising a polymerizable liquid crystal compound and a dye,
A composition in which the maximum absorption wavelength of the dye satisfies the following relation (11):
λ max2 −λ max1 <0 (11)
(In formula (11), λ max1 represents the maximum absorption wavelength of the dye in a solvent, and λ max2 represents the maximum absorption wavelength of the dye in a dye film formed using the composition.)
The composition according to claim 11, wherein the dye is an azo dye.
The composition according to claim 12, wherein the dye is a compound represented by the following formula (12):
X 20 (-A 21 ) m1 (-N=N-A 22 ) n1 -N=N-A 23 -Y 20 (12)
(In formula (12),
-A 21 -, -A 22 -, and -A 23 - each independently represent a divalent group of an aromatic hydrocarbon ring which may have a substituent, or an aromatic heterocycle which may have a substituent;
-X 20 and -Y 20 each independently represent an arbitrary monovalent substituent;
m1 represents 1 or 2;
n1 represents 0, 1, 2, or 3.
When m1 is 2, -A 21 - may be the same or different.
When n1 is 2 or 3, -A 22 - may be the same or different.
The composition according to claim 13, wherein in formula (12), -A 21 - and -A 23 - each independently represent a divalent group of an aromatic hydrocarbon ring which may have a substituent.
The composition according to claim 13, wherein in the formula (12), -A 22 - is a divalent group of an aromatic hydrocarbon ring which may have a substituent.
The composition according to claim 13, wherein in the formula (12), -Y 20 is represented by the following formula (12a):
-N-(R y )-R x (12a)
(In formula (12a), -R x and -R y each independently represent an alkyl group or an aryl group which may have a branch, and the alkyl group or aryl group may have a substituent. -R x and -R y may together form a ring having 2 to 15 carbon atoms together with N, and the ring may have a substituent.)
The composition according to claim 11, wherein the polymerizable liquid crystal compound is a low molecular weight polymerizable liquid crystal compound that does not have a copolymer structure.
An anisotropic dye film formed using the composition according to any one of claims 11 to 17.
An optical element comprising the anisotropic dye film according to claim 18.