JP2021047249A - Anisotropic dye film forming composition, anisotropic dye film, and optical element - Google Patents

Abstract

To provide: a polymerizable anisotropic dye film forming composition capable of realizing a low isotropic phase-emerging temperature while maintaining excellent optical performance, in particular a sufficient dichroic ratio; an anisotropic dye film forming composition that can have a low haze and a good appearance; an anisotropic dye film which can maintain excellent optical performance, in particular a sufficient dichroic ratio, and can form a stable structure at lower temperature; and an anisotropic dye film which has a low haze, a good appearance, and mechanical strength.SOLUTION: The anisotropic dye film forming composition comprises a dye and a liquid crystal compound, where the liquid crystal compound includes a liquid crystal compound represented by formula (1), R1-A1-Y1-A2-Y2-A3-R2.SELECTED DRAWING: None

Description

The present invention is an anisotropic dye film formed by applying a liquid crystal composition, particularly a polarizing film provided in a display element of a dimming element, a liquid crystal element (LCD), and an organic electroluminescence element (OLED). The present invention relates to an anisotropic dye film forming composition and an anisotropic dye film exhibiting high dichroism, and an optical element, which are useful for the above.

In the LCD, a linear polarizing film and a circular polarizing film are used in order to control the optical rotation and birefringence in the display. Also in the OLED, a circular polarizing film is used to prevent reflection of external light in a bright place.
Conventionally, as such a polarizing film, for example, a polarizing film obtained by dyeing polyvinyl alcohol (PVA) with a low concentration of iodine (iodine-PVA polarizing film) is known (Patent Document 1).
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 Unexamined Patent Publication No. 1-105204 Special Table 2004-535483

However, the iodine-PVA polarizing plate having such a low concentration alleviates the problem that iodine sublimates or deteriorates depending on the usage environment and the color changes, and the stretching of PVA is alleviated. There is a problem that warpage occurs due to

Further, in a polarizing film formed by applying a liquid crystal composition containing a dye, high light absorption selection performance cannot be obtained, or if high light absorption selection performance is to be obtained, process difficulties occur. There is a problem that there are times. Further, when it is used for LCD and OLED applications, it is required to have good appearance performance.
Under such circumstances, a polarizing film having a good appearance and having high light absorption selection performance even in a thin film is desired.

By the way, in the process of producing the anisotropic dye film, the composition for forming the anisotropic dye film is applied to the substrate, and in the orientation process performed as necessary after drying, the composition for forming the anisotropic dye film is formed. After heating to an isotropic phase appearance temperature or higher, cooling is performed so that the liquid crystal phase is formed again. Alternatively, cooling is performed after heating to a temperature at which a highly fluid liquid crystal phase (for example, a nematic phase) appears. From this, the composition for forming an anisotropic dye film having a high isotropic phase appearance temperature requires a higher temperature in the above-mentioned orientation process, and the stability of the dye and the liquid crystal compound, the ease of handling of the process, and the like. It is disadvantageous from the viewpoint of energy consumption. Furthermore, when the liquid crystal compound has a polymerizable group, unintended thermal polymerization may occur due to heating at a high temperature in the above reorientation process. Further, depending on the heat resistant temperature of the base material, the degree of freedom in selecting a base material that can be used decreases.

On the other hand, in order to enhance the dichroism of the anisotropic dye film formed from the anisotropic dye film forming composition, the core of the liquid crystal compound molecule contained in the anisotropic dye film forming composition is used. It is conceivable to increase the ratio of the long axis to the short axis.
However, when the core of the liquid crystal compound molecule is enlarged, the melting point of the liquid crystal compound (phase transition point between solid and liquid) and the isotropic phase appearance temperature (phase transition point between liquid crystal and liquid) tend to increase.
That is, if an attempt is made to lower the isotropic phase appearance temperature, it is conceivable to make the core of the liquid crystal compound molecule smaller, while by making the core of the liquid crystal compound molecule smaller, the major axis and the short axis of the core of the liquid crystal compound molecule are shortened. The ratio of the axes becomes small, and as a result, the bichromaticity of the anisotropic dye film formed from the composition for forming the anisotropic dye film is lowered.

Under such circumstances, the isotropic appearance temperature of the anisotropic dye film forming composition is adjusted while maintaining high dichroism of the anisotropic dye film formed from the anisotropic dye film forming composition. It is desired to lower it.

On the other hand, in order to enhance the dichroism of the anisotropic dye film formed from the anisotropic dye film forming composition, the liquid crystal compound molecules contained in the anisotropic dye film forming composition are used. It is conceivable to increase the ratio of the major axis to the minor axis of the core to orient the liquid crystal molecules in the uniaxial direction.
However, when the core of the liquid crystal compound molecule is enlarged, the core is composed of an aromatic ring such as a benzene ring and an alicyclic ring such as a cyclohexane ring. On the other hand, the molecules tend to be tilted and oriented.
That is, in order to orient the liquid crystal compound molecule in the uniaxial direction, it is conceivable to reduce the core of the liquid crystal compound molecule, reduce the interaction between the molecules, and reduce the inclination of the molecule, while reducing the inclination of the liquid crystal compound molecule. By making the core smaller, the ratio of the major axis to the minor axis of the core of the liquid crystal compound molecule becomes smaller, and as a result, the two colors of the anisotropic dye film formed from the composition for forming the anisotropic dye film. The sex will be lowered.

The anisotropic dye film formed from the composition for forming an anisotropic dye film is required to have a low haze in terms of appearance performance. In order to lower the haze, it is conceivable to suppress orientation defects of the liquid crystal compound in the anisotropic dye film and structural defects of the anisotropic dye film, which cause haze. Examples of defects of the anisotropic dye film include defects derived from molecular orientation, defects derived from the internal structure of the film, defects derived from the surface structure of the film, defects derived from precipitates, and the like.

The anisotropic dye film formed from the composition for forming an anisotropic dye film is also required to have mechanical strength and stability of the anisotropic dye film structure from the viewpoints of practical use and production. In order to impart mechanical strength and stability of the film structure, it is conceivable to polymerize the anisotropic dye film. However, if the degree of polymerization is increased in order to increase the mechanical strength and the stability of the film structure, defects of the anisotropic dye film are likely to occur due to polymerization strain in the step of polymerizing the composition for forming the anisotropic dye film. , There is a risk that the haze will grow.

In view of the above problems, the present invention provides a polymerizable anisotropic dye film forming composition capable of achieving a low isotropic phase appearance temperature while maintaining excellent optical performance, particularly a sufficient two-color ratio. The purpose is to do. A further object of the present invention is to provide a composition for forming an anisotropic dye film having a low haze and a good appearance.
Another object of the present invention is to provide an anisotropic dye film capable of maintaining excellent optical performance, particularly a sufficient dichroic ratio, and forming a stable structure at a lower temperature. A further object of the present invention is to provide an anisotropic dye film having a low haze, a good appearance, and mechanical strength.

The present inventors have found that the above-mentioned problems can be solved by using a liquid crystal compound having a specific structure in a composition for forming an anisotropic dye film containing a dye and a liquid crystal compound.
That is, the gist of the present invention is as follows.

[1] An anisotropic dye film forming composition containing a dye and a liquid crystal compound.
A composition for forming an anisotropic dye film, wherein the liquid crystal compound contains a liquid crystal compound represented by the formula (1).
R1-A1-Y1-A2-Y2-A3-R2 ... (1)
In equation (1),
R1 and R2 represent a chain organic group having a polymerizable group on one side and a non-polymerizable chain organic group on the other side;
The sum of the chain lengths of R1 and R2 is 7 or more;
A1 and A3 independently represent a partial structure represented by the formula (2), a divalent organic group, or a single bond;
A2 represents a partial structure or a divalent organic group represented by the formula (2);
-Y1- and -Y2- are independently single-bonded, -C (= O) O-, -OC (= O)-, -C (= S) O-, -OC (= S)-, respectively. -C (= O) S-, -SC (= O)-, -CH ₂ CH _2- , -CH = CH-, -C (= O) NH-, -NHC (= O)-, -CH ₂ Represents O-, -OCH _2- , -CH ₂ S-, or -SCH _2- ;
One of A1 and A3 is a partial structure or a divalent organic group represented by the formula (2);
At least one of A1, A2, and A3 is a partial structure represented by the formula (2).
-Cy-X2-C≡C-X-... (2)
In equation (2),
Cy represents a hydrocarbon ring group or a heterocyclic group;
-X- is -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 Represents S- or -SCH _2- ;
-X2- is 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- , Represents −CH ₂ S− or −SCH _2−.
[1] In [1], -X- is -C (= O) O-, -OC (= O)-, -CH ₂ CH _2- , -CH ₂ O-, or -OCH _2- . The composition for forming an anisotropic dye film according to the above.
[3] The composition for forming an anisotropic dye film according to [1] or [2], wherein Cy in the formula (2) is a hydrocarbon ring group and -X2- is a single bond.
[4] One of A1, A2, and A3 is a partial structure represented by the above formula (2), and the other two are independently divalent organic groups.
In the formula (2), Cy is a hydrocarbon ring group, -X2- is a single bond, and
The composition for forming an anisotropic dye film according to any 11 of [1] to [3], wherein the divalent organic group is a hydrocarbon ring group.
[5] The anisotropic dye film according to any one of [1] to [4], wherein Cy in the formula (2) is a 1,4-phenylene group or a cyclohexane-1,4-diyl group. Composition for formation.
[6] The composition for forming an anisotropic dye film according to any one of [1] to [5], wherein Cy in the formula (2) is a 1,4-phenylene group.
[7] The polymerizable chain organic group is − (CH ₂ ) _n − polymerizable group, −O − (CH ₂ ) _n-1 -polymerizable group, and n is an integer of 3 or more. , The composition for forming an anisotropic dye film according to any one of [1] to [6].
[8] The anisotropic chain according to any one of [1] to [7], wherein the non-polymerizable chain organic group is a linear or branched alkyl group having a chain length of 6 or more. Composition for forming a sex pigment film.
[9] -Y1- and -Y2- are independently single-bonded, -C (= O) O-, -OC (= O)-, -CH ₂ CH _2- , -CH ₂ O- or-, respectively. OCH _2- and
-X- is -C (= O) O-, -OC (= O)-, -CH ₂ CH _2- , -CH ₂ O- or -OCH _2- , [1] to [8] The composition for forming an anisotropic dye film according to any one.
[10] The composition for forming an anisotropic dye film according to any one of [1] to [1], wherein one of A1 and A3 is a cyclohexane-1,4-diyl group.
[11] In any one of [1] to [10], one of A1 and A3 has a partial structure represented by the above formula (2), and the other is a cyclohexane-1,4-diyl group. The composition for forming an anisotropic dye film according to the above.
[12] An anisotropic dye film formed by using the composition for forming an anisotropic dye film according to any one of [1] to [11].
[13] An optical element including the anisotropic dye film according to [12].

The composition for forming an anisotropic dye film of the present invention is polymerizable, and can realize a low isotropic phase appearance temperature while maintaining excellent optical performance, particularly a sufficient two-color ratio. Further, the composition for forming an anisotropic dye film of the present invention has a low haze and a good appearance.
Since the anisotropic dye film of the present invention is formed by using the composition for forming an anisotropic dye film of the present invention, excellent optical performance, particularly a sufficient dichroic ratio can be maintained, and the anisotropic dye film is formed at a lower temperature. It is possible to do. Further, the anisotropic dye film of the present invention has a low haze, a good appearance, mechanical strength, and a stable structure.
Since the optical element of the first aspect of the present invention contains the anisotropic dye film of the present invention, excellent optical performance, particularly a sufficient dichroic ratio can be maintained, and a stable structure can be formed at a lower temperature. It is possible to include an anisotropic dye film which has a low haze, a good appearance, and can have mechanical strength.

Hereinafter, embodiments of the present invention will be specifically described, but the present invention is not limited to the following embodiments, and can be variously modified and implemented within the scope of the gist thereof.

The anisotropic dye film referred to in the present invention has electromagnetic properties in any two directions selected from a total of three directions in a three-dimensional coordinate system in the thickness direction of the anisotropic dye film and two arbitrary in-plane directions. It is a dye film having anisotropy. Examples of electromagnetic properties include optical properties such as absorption and refraction, and electrical properties such as resistance and capacitance.
Examples of the film having optical anisotropy such as absorption and refraction include a linear polarizing film, a polarizing film such as a circular polarizing film, a retardation film, and a conductive anisotropic dye film. The anisotropic dye film 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.

[Composition for forming an anisotropic dye film]
The composition for forming an anisotropic dye film of the present invention contains a dye and a liquid crystal compound.
The composition for forming an anisotropic dye film of the present invention may be a solution, a liquid crystal, or a dispersed state as long as it does not cause phase separation, but the anisotropic dye film may be in a dispersed state. The forming composition is preferably a solution from the viewpoint of easy application to the substrate. On the other hand, the solid content component obtained by removing the solvent from the composition for forming an anisotropic dye film is preferably in a liquid crystal phase at an arbitrary temperature from the viewpoint of orientation on the substrate as described later.
In the present invention, the state of the liquid crystal phase is specifically described on pages 1 to 16 of "Basics and Applications of Liquid Crystals" (Shoichi Matsumoto, Ryo Tsunoda; 1991). As described above, it is a liquid crystal state exhibiting both liquid and crystal properties or intermediate properties, and is a nematic phase, a smectic phase, a cholesteric phase, or a discotic phase.

The reason why the composition for forming an anisotropic dye film of the present invention exerts the above-mentioned effects is not clear, but the following can be considered.
The liquid crystal compound contained in the composition for forming an anisotropic dye film of the present invention has a high ratio of the major axis to the minor axis of the core structure to facilitate uniaxial orientation of the liquid crystal molecules, and has the same core size. It is considered that a low isotropic phase appearance temperature can be realized while maintaining excellent optical performance, particularly a sufficient two-color ratio, because the size of the anisotropic expression temperature is suppressed to a size that does not increase the temperature.
Further, when the liquid crystal compound has a polymerization functional group in the immediate vicinity of the liquid crystal core, the molecules tend to be difficult to associate with each other due to the motility of the polymerization functional group or steric hindrance, and the liquid crystal compound tends not to show a liquid crystal state. The liquid crystal compound contained in the composition for forming an anisotropic dye film of the present invention has a chain-like organic group as a side chain, and the liquid crystal phase is formed by setting the sum of the chain lengths to 7 or more. It is considered that it can be expressed and can show a high two-color ratio.
The liquid crystal compound contained in the composition for forming an anisotropic dye film of the present invention has a chain organic group having a polymerizable group and a chain organic group having no polymerizable group, and the sum of the chain lengths thereof. It is considered that by setting the length to 7 or more, the polymerization strain that induces defects in the film structure can be alleviated by the chain organic group, and a film having a low haze and a good appearance can be obtained.
In the liquid crystal compound contained in the composition for forming an anisotropic dye film of the present invention, in addition to the chain-like organic group having a polymerizable group, the chain-like organic group having no polymerizable group is also included in the side chain. Therefore, it is less susceptible to distortion due to polymerization even in the polymerization step for forming an anisotropic dye film, and it is possible to secure the molecular orientation of the liquid crystal compound and exhibit a high two-color ratio. It is considered that an anisotropic dye film having a low haze and a good appearance can be obtained by suppressing the alignment defect and the defect of the film structure.
The liquid crystal compound contained in the composition for forming an anisotropic dye film of the present invention has a chain-like organic group having a polymerizable group in the side chain and a chain-like organic group having no polymerizable group in the side chain. It is considered that the orientation can be improved and the two-color ratio can be increased, the polymerization distortion in the polymerization step of forming the anisotropic dye film is less likely to occur, and the haze can be lowered.
The liquid crystal compound contained in the composition for forming an anisotropic dye film of the present invention has a composition for forming an anisotropic dye film that can be polymerized by having a chain organic group having a polymerizable group in one side chain. It is considered that an anisotropic dye film having good mechanical strength and film structure stability can be obtained as a product.

<Liquid crystal compound>
In the present invention, the liquid crystal compound refers to a substance indicating a liquid crystal state, and specifically, it is described on pages 1 to 28 of "Liquid Crystal Handbook" (Maruzen Co., Ltd., published on October 30, 2000). As described above, a compound that does not directly transfer from a crystal to a liquid but becomes a liquid through an intermediate state exhibiting the properties of both a crystal and a liquid.

The liquid crystal compound contained in the composition for forming an anisotropic dye film according to the first aspect of the present invention includes a liquid crystal compound represented by the following formula (1).
R1-A1-Y1-A2-Y2-A3-R2 ... (1)
In equation (1),
R1 and R2 represent a chain organic group having a polymerizable group on one side and a non-polymerizable chain organic group on the other side;
The sum of the chain lengths of R1 and R2 is 7 or more;
A1 and A3 independently represent a partial structure represented by the formula (2), a divalent organic group, or a single bond;
A2 represents a partial structure or a divalent organic group represented by the formula (2);
-Y1- and -Y2- are independently single-bonded, -C (= O) O-, -OC (= O)-, -C (= S) O-, -OC (= S)-, respectively. -C (= O) S-, -SC (= O)-, -CH ₂ CH _2- , -CH = CH-, -C (= O) NH-, -NHC (= O)-, -CH ₂ Represents O-, -OCH _2- , -CH ₂ S-, or -SCH _2- ;
One of A1 and A3 is a partial structure or a divalent organic group represented by the formula (2);
At least one of A1, A2, and A3 is a partial structure represented by the formula (2).
-Cy-X2-C≡C-X-... (2)
In equation (2),
Cy represents a hydrocarbon ring group or a heterocyclic group;
-X- is -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 Represents S- or -SCH2-;
-X2- is 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- , Represents −CH ₂ S− or −SCH _2−.

(A1, A2 and A3)
A1 and A3 independently represent a partial structure or a divalent organic group represented by the formula (2), or a single bond, and A2 represents a partial structure or a divalent organic group represented by the formula (2). Represent.

(Q1)
The divalent organic group in A1, A2, and A3 is not particularly limited, but is preferably a group represented by the following formula (3).
−Q1- ・ ・ ・ (3)
In formula (3), Q1 represents a hydrocarbon ring group or a heterocyclic group.

((Hydrocarbon ring group in Q1))
The hydrocarbon ring group in Q1 includes an aromatic hydrocarbon ring group and a non-aromatic hydrocarbon ring group.
Aromatic hydrocarbon ring groups include unlinked aromatic hydrocarbon ring groups and linked aromatic hydrocarbon ring groups.
The unlinked aromatic hydrocarbon ring group is a divalent group of a monocyclic or condensed aromatic hydrocarbon ring, and the number of carbon atoms is preferably 6 to 20 and more preferably 6 to 14 from the viewpoint of expressing liquidity. Further, in the case of condensation, the number of rings is not particularly limited, but 1 to 4 is preferable from the viewpoint of solubility.
Examples 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. ..
A linked aromatic hydrocarbon ring group is a divalent group in which a plurality of monocyclic or condensed aromatic hydrocarbon rings are bonded by a single bond and have a bond on an atom constituting the ring. The carbon number of the monocyclic or condensed ring is preferably 6 to 20 from the viewpoint of developing liquid crystallinity. In the case of condensation, the number of rings is not particularly limited, but 1 to 4 is preferable from the viewpoint of solubility.
For example, a first monocyclic or condensed aromatic hydrocarbon ring having 6 to 20 carbon atoms and a second monocyclic or condensed aromatic hydrocarbon ring having 6 to 20 carbon atoms are bonded by a single bond, and the first A single ring having 6 to 20 carbon atoms or a condensed aromatic hydrocarbon ring having a first bond on the atom constituting the ring of the hydrocarbon ring, and a second monocyclic ring or condensed aromatic ring having 6 to 20 carbon atoms. It is a divalent group having a second bond on the atom constituting the ring of the group hydrocarbon ring. 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.
Of these, as the aromatic hydrocarbon ring group, a divalent group of a benzene ring and a divalent group of a naphthalene ring are preferable from the viewpoint of solubility, and a divalent group of a benzene ring (phenylene group) is more preferable. As the phenylene group, a 1,4-phenylene group is preferable from the viewpoint of solubility and molecular orientation of the liquid crystal compound.

The non-aromatic hydrocarbon ring group includes a non-linked non-aromatic hydrocarbon ring group and a linked non-aromatic hydrocarbon ring group.
The unlinked non-aromatic hydrocarbon ring group is a divalent group of a monocyclic or condensed non-aromatic hydrocarbon ring, and the number of carbon atoms is preferably 3 to 20 from the viewpoint of facilitating synthesis, and more preferably 4. 6 or 8. In the case of condensation, the number of rings is not particularly limited, but 1 to 5 is preferable from the viewpoint of solubility.
Examples of the non-aromatic hydrocarbon ring 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 bornan ring, an adamantane ring, a tetrahydronaphthalene ring, and a bicyclo [2]. .2.2] Octane ring and the like can be mentioned.
The non-linked non-aromatic hydrocarbon ring group includes an alicyclic hydrocarbon ring group having no unsaturated bond as an interatomic bond constituting the ring of the non-aromatic hydrocarbon ring and a ring of the non-aromatic hydrocarbon ring. It contains an unsaturated non-aromatic hydrocarbon ring group having an unsaturated bond as an interatomic bond constituting the above. As the unlinked non-aromatic hydrocarbon ring group, an alicyclic hydrocarbon ring group is preferable from the viewpoint of solubility.

The linked non-aromatic hydrocarbon ring group is a divalent group or a monocyclic group in which a plurality of monocyclic or condensed non-aromatic hydrocarbon rings are bonded by a single bond and has a bond on the atom constituting the ring. A single ring or a single ring or one or more rings selected from the group consisting of an aromatic hydrocarbon ring, a condensed aromatic hydrocarbon ring, a monocyclic non-aromatic hydrocarbon ring, and a condensed non-aromatic hydrocarbon ring. It is a divalent group in which a fused non-aromatic hydrocarbon ring is bonded in a single bond and has a bond on the atom constituting the ring. The number of carbon atoms of the monocyclic ring or the fused ring is preferably 3 to 20, more preferably 4 to 10 from the viewpoint of facilitating synthesis. In the case of condensation, the number of rings is not particularly limited, but 1 to 5 is preferable from the viewpoint of solubility.
For example, a first monocyclic or condensed non-aromatic hydrocarbon ring having 3 to 20 carbon atoms and a second monocyclic or condensed non-aromatic hydrocarbon ring having 3 to 20 carbon atoms are bonded in a single bond. , A first single bond having a first bond on an atom constituting a first monocyclic ring having 3 to 20 carbon atoms or a fused non-aromatic hydrocarbon ring, or a second monocyclic ring having 3 to 20 carbon atoms. It is a divalent group having a second bond on the atom constituting the ring of the fused non-aromatic hydrocarbon ring, and is, for example, a monocyclic ring having 3 to 20 carbon atoms or a fused aromatic hydrocarbon ring and the number of carbon atoms. The first on the atom constituting the ring of the monocyclic or fused aromatic hydrocarbon ring having 3 to 20 carbon atoms, which is bonded by a single bond with 3 to 20 monocyclic or condensed non-aromatic hydrocarbon rings. It is a divalent group having a bond and having a second bond on an atom constituting a monocyclic ring having 3 to 20 carbon atoms or a fused ring of a non-aromatic hydrocarbon ring. Examples of the linked non-aromatic hydrocarbon ring group include a bis (cyclohexane) -4,4'-diyl group and a 1-cyclohexylbenzene-4,4'-diyl group.

As the non-aromatic hydrocarbon ring group, a non-linked non-aromatic hydrocarbon ring group is preferable.
Of these, as the 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 from the viewpoint of solubility and molecular orientation of the liquid crystal compound.

((Heterocyclic group in Q1))
The heterocyclic group in Q1 includes an aromatic heterocyclic group and a non-aromatic heterocyclic group. The aromatic heterocyclic group includes a non-linked aromatic heterocyclic group and a linked aromatic heterocyclic group.
The unlinked aromatic heterocyclic group is a divalent group of a monocyclic or condensed aromatic heterocycle, and the number of carbon atoms is preferably 4 to 20, more preferably 4 to 16, from the viewpoint of facilitating synthesis. In the case of condensation, the number of rings is not particularly limited, but 1 to 5 is preferable from the viewpoint of solubility.
Examples of the aromatic heterocycle include a furan ring, a benzofuran ring, a thiophene ring, a benzothiophene ring, a pyrazole ring, a pyrazole ring, an imidazole ring, an oxadiazole ring, an indole ring, a carbazole ring, a pyroloymidazole ring, a pyrrolopyrazole ring, and a pyrrolopyrrole. Ring, thienopyrrole ring, thienothiophene ring, flopyrol ring, flofuran ring, thienofuran ring, thienothiazole ring, benzoisoxazole ring, benzoisothiazole ring, benzimidazole ring, pyridine ring, pyrazine ring, pyridazine ring, pyrimidine ring, triazine ring , Kinolin ring, isoquinolin ring, sinoline ring, quinoxalin ring, phenanthridin ring, benzimidazole ring, pyrimidine ring, quinazoline ring, quinazolinone ring, azulene ring and the like.

A linked aromatic heterocyclic group is a divalent group in which a plurality of monocyclic or condensed aromatic heterocycles are bonded by a single bond and have a bond on an atom constituting the ring. The number of carbon atoms in the monocyclic or condensed ring is preferably 4 to 20 from the viewpoint of facilitating synthesis. In the case of condensation, the number of rings is not particularly limited, but 1 to 5 is preferable from the viewpoint of solubility.
For example, a first monocyclic or condensed aromatic heterocycle having 4 to 20 carbon atoms and a second monocyclic or condensed aromatic heterocycle having 4 to 20 carbon atoms are bonded by a single bond, and the first A monocyclic or fused aromatic heterocycle having a first bond on an atom constituting a monocyclic or fused aromatic heterocycle having 4 to 20 carbon atoms and a second monocyclic or condensed aromatic heterocycle having 4 to 20 carbon atoms. It is a divalent group having a second bond on the atom constituting the ring of.

The non-aromatic heterocyclic group includes a non-linked non-aromatic heterocyclic group and a linked non-aromatic heterocyclic group.
The unlinked non-aromatic heterocyclic group is a divalent group of a monocyclic or condensed non-aromatic heterocycle, and the number of carbon atoms is preferably 4 to 20 from the viewpoint of facilitating synthesis. In the case of condensation, the number of rings is not particularly limited, but 1 to 5 is preferable from the viewpoint of solubility.
It is a divalent group of a monocyclic or condensed non-aromatic heterocycle having 4 to 20 carbon atoms, and examples of the non-aromatic heterocycle include a tetrahydrofuran ring, a tetrahydropyran ring, a dioxane ring, a tetrahydropyran ring, and a tetrahydropyran ring. Pyrrolidine ring, piperidine ring, dihydropyridine ring, piperazine ring, tetrahydrothiazole ring, tetrahydrooxazole ring, octahydroquinoline ring, tetrahydroquinoline ring, octahydroquinazoline ring, tetrahydroquinazoline ring, tetrahydroimidazole ring, tetrahydrobenzoimidazole ring, quinuclidine ring, etc. Can be mentioned.

A linked non-aromatic heterocyclic group is a divalent group in which a plurality of monocyclic or condensed non-aromatic heterocycles are bonded by a single bond and have a bond on an atom constituting the ring. The number of carbon atoms in the monocyclic or condensed ring is preferably 4 to 20 from the viewpoint of facilitating synthesis. In the case of condensation, the number of rings is not particularly limited, but 1 to 5 is preferable from the viewpoint of solubility.
For example, a first monocyclic or condensed non-aromatic heterocycle having 4 to 20 carbon atoms and a second monocyclic or condensed non-aromatic heterocycle having 4 to 20 carbon atoms are bonded in a single bond to form a first bond. It has a first bond on an atom constituting a monocyclic ring having 4 to 20 carbon atoms or a fused non-aromatic heterocyclic ring, and a second monocyclic ring having 4 to 20 carbon atoms or a fused non-aromatic ring. It is a divalent group having a second bond on the atom constituting the ring of the aromatic heterocycle.

The aromatic hydrocarbon ring group, non-aromatic hydrocarbon ring group, aromatic heterocyclic group, and non-aromatic heterocyclic group in Q1 are RA, -OH, -O-RA, and -OC (= O, respectively). ) -RA, -NH ₂ , -NH-RA, -N (RB) -RA, -C (= O) -RA, -C (= O) -O-RA, -C (= O) -NH ₂ , -C (= O) -NH-RA, -C (= O) -N (RB) -RA, -SH, -S-RA, trifluoromethyl group, sulfamoyl group, carboxy group, sulfo group, cyano group , Nitro groups, and one or more groups selected from the group consisting of halogens. Here, RA and RB each independently represent a linear or branched alkyl group having 1 to 6 carbon atoms.

The aromatic hydrocarbon ring group, the non-aromatic hydrocarbon ring group, the aromatic heterocyclic group, and the non-aromatic heterocyclic group in Q1 have high linearity in molecular structure, and the liquid crystal compounds represented by the formula (1) are used with each other. It is preferable that each of them is independently unsubstituted or substituted with a methyl group, a methoxy group, a fluorine atom, a chlorine atom, and a bromine atom, from the viewpoint that they are easily associated with each other and easily develop a liquid crystal state. Is more preferable.
The substituents of the aromatic hydrocarbon ring group, the non-aromatic hydrocarbon ring group, the aromatic heterocyclic group, and the non-aromatic heterocyclic group may be the same or different, and the aromatic hydrocarbon ring group, All of the non-aromatic hydrocarbon ring group, aromatic heterocyclic group, and non-aromatic heterocyclic group may be substituted, all of them may be unsubstituted, and some of them may be substituted and some of them may be substituted. It may be non-replacement.
Further, the substituents of the divalent organic groups in A1, A2, and A3 may be the same or different, and all of the divalent organic groups in A1, A2, and A3 may be substituted, and all of them may be substituted. It may be unsubstituted, or it may be partially substituted and partially unsubstituted.

As the divalent organic group, it is preferable that Q1 is a hydrocarbon ring group, that is, the divalent organic group is a hydrocarbon ring group. Further, as the divalent organic group, a divalent group (phenylene group) of a benzene ring and a divalent group (cyclohexanediyl group) of cyclohexane are more preferable, and the linearity of the molecular structure of the liquid crystal compound can be increased. A 1,4-phenylene group and a cyclohexane-1,4-diyl group are more preferable.

((Combination of A1, A2, and A3))
When A1 is a partial structure represented by the formula (2), the formula (1) is
R1-Cy-X2-C≡C-X-Y1-A2-Y2-A3-R2 ... (1A)
May be
R1-X-C≡C-X2-Cy-Y1-A2-Y2-A3-R2 ... (1B)
It may be.
Further, when A2 is a partial structure represented by the equation (2), the equation (1) is:
R1-A1-Y1-Cy-X2-C≡C-X-Y2-A3-R2 ... (1C)
May be
R1-A1-Y1-X-C≡C-X2-Cy-Y2-A3-R2 ... (1D)
It may be.
Further, when A3 is a partial structure represented by the equation (2), the equation (1) is:
R1-A1-Y1-A2-Y2-Cy-X2-C≡C-X-R2 ... (1E)
May be
R1-A1-Y1-A2-Y2-X-C≡C-X2-Cy-R2 ... (1F)
It may be.

Similarly, when two or more of A1, A2, and A3 are substructures represented by the formula (2), the directions of the substructures represented by the formula (2) are independently reversed. You may.

Further, as described above, A1, A2, and A3 are each independently a partial structure or a divalent organic group represented by the formula (2). In addition, A1 and A3 may be single bonds, but neither A1 nor A3 are single bonds.
At least one of A1, A2, and A3 represents a partial structure represented by the above formula (2). Further, in the case of the partial structure represented by the above formula (2), it is preferable that the other two are independently divalent organic groups. Further, among A1, A2 and A3, it is preferable. It is preferable that one Cy of the partial structure represented by the formula (2) is a hydrocarbon ring group, and the other two are preferably divalent organic groups, and in particular, the hydrocarbon ring as the divalent organic group. It is preferably a group. In particular, the hydrocarbon ring group is preferably a 1,4-phenylene group or a cyclohexane-1,4-diyl group, and one of A1 or A3 is particularly a cyclohexane-1,4-diyl group. preferable.
Further, it is more preferable that one of A1 and A3 has a partial structure represented by the formula (2) and the other is a divalent organic group. Further, it is more preferable that A2 is a divalent organic group. In this case, one of A1 and A3 which is a divalent organic group is preferably a cyclohexane-1,4-diyl group. Further, it is particularly preferable that A2 is a 1,4-phenylene group.

(Equation (2) X)
-X- is -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 Represents S- or -SCH _2-.
With these structures, the linearity of the liquid crystal compound and the rotational movement around the short axis of the molecule tend to be easy, and the above structure having a small π bond property is suitable. Among these, −C (= O) O−, −OC (= O) −, −CH ₂ CH ₂ −, −CH ₂ O− or −OCH ₂₋ are more preferable because of the above-mentioned tendency.
In particular, -Y1- and -Y2- are independently single-bonded, -C (= O) O-, -OC (= O)-, -CH ₂ CH _2- , -CH ₂ O-, or-. OCH ₂ −, and −X− may be −C (= O) O−, −OC (= O) −, −CH ₂ CH ₂₋ , −CH ₂ O−, or −OCH _2−. There is a tendency to increase the molecular orientation of the liquid crystal compound.

(Equation (2) X2)
-X2- is 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- , Represents −CH ₂ S− or −SCH _2−. With these structures, the linearity of the liquid crystal compound and the rotational movement around the short axis of the molecule tend to be easy, and the above structure having a small π bond property is suitable. Among these, since the above tendency is further observed, -C (= O) O-, -OC (= O)-, -C (= S) O-, -OC (= S)-, and -C (= O) ) S-, -SC (= O)-, -CH = CH-, -C (= O) NH-, -NHC (= O)-is preferable, and since it has higher linearity, it is a single bond. More preferably.

(Equation (2) Cy)
Cy represents a hydrocarbon ring group or a heterocyclic group.
The hydrocarbon ring group or heterocyclic group of Cy has the same meaning as Q1 described above, and the preferable range also has the same meaning.
In particular, as Cy, a hydrocarbon ring group is preferable, and a phenylene group and a cyclohexanediyl group are more preferable. Further, as Cy, a 1,4-phenylene group and a cyclohexane-1,4-diyl group are more preferable, and a 1,4-phenylene group is particularly preferable, because the linearity of the molecular structure of the liquid crystal compound can be increased. ..
-Cy- and -C≡C- with highly linear groups from the viewpoint of increasing the core of the liquid crystal compound and increasing the dichroism of the anisotropic dye film formed from the composition for forming an anisotropic dye film. It is preferable to connect the two.
Examples of the group having high linearity include -C (= O) O-, -OC (= O)-, and -C (= S) O-, which have a single bond or a π bond as the above-mentioned -X2-. -OC (= S)-, -C (= O) S-, -SC (= O)-, -CH = CH-, -C (= O) NH-, -NHC (= O)- Is preferable, and a single bond is more preferable because the linearity is higher.
Since the linearity of the molecular structure of the liquid crystal compound tends to be particularly high, it is preferable that Cy is a hydrocarbon ring group and -X2- is a single bond.

(R1 and R2)
One of R1 and R2 represents a chain organic group having a polymerizable group, and the other represents a chain organic group having no polymerizable group, and the sum of the chain lengths of R1 and R2 is 7 or more. Which of R1 and R2 may be a chain organic group having a polymerizable group or a non-polymerizable chain organic group.
The chain organic groups in R1 and R2 do not contain cyclic structures such as the above-mentioned aromatic hydrocarbon ring, non-aromatic hydrocarbon ring, aromatic heterocycle, non-aromatic heterocycle (however, the chain in R1 and R2). When the organic group has a cyclic polymerizable group such as an oxylane ring, an oxetane ring, a vinylbenzene ring, etc., which will be described later, the portion excluding the polymerizable group does not include the above cyclic structure.) Monovalent It is an organic group.

The chain lengths of R1 and R2 represent the number of atoms in the main chain of the chain organic group having a polymerizable group (excluding the polymerizable portion of the polymerizable group described later).
The sum of the chain lengths of R1 and R2 is 7 or more, preferably 8 or more, more preferably 9 or more, still more preferably 10 or more, and particularly preferably 12 or more. Further, it is preferably 36 or less, more preferably 30 or less, further preferably 26 or less, and particularly preferably 24 or less. When it is at least the above lower limit, the liquid crystal property is exhibited and the effect of lowering the isotropic phase expression temperature tends to be obtained, and when it is at least the above upper limit, defects are suppressed when forming an anisotropic dye film. It tends to be effective.

As long as the sum of the chain lengths of R1 and R2 is 7 or more, the respective chain lengths are not particularly limited. The chain length of the chain organic group having a polymerizable group is preferably 1 or more, more preferably 2 or more, still more preferably 3 or more, still more preferably 6 or more, and particularly preferably 7 or more. It is more than that, and more preferably 8 or more. Further, it is preferably 20 or less, more preferably 15 or less, further preferably 14 or less, and particularly preferably 12 or less. On the other hand, the chain length of the non-polymerizable chain organic group is preferably 1 or more, more preferably 2 or more, still more preferably 3 or more, still more preferably 6 or more, and in particular. It is preferably 7 or more, and more preferably 8 or more. Further, it is preferably 20 or less, more preferably 15 or less, further preferably 14 or less, and particularly preferably 12 or less.
When it is at least the above lower limit, liquid crystallinity is exhibited, and the effect of lowering the isotropic phase expression temperature tends to be obtained. When it is at least the above upper limit, defects are caused when forming an anisotropic dye film. There is a tendency to obtain an inhibitory effect.

As chain organic groups, − (CH ₂ ) _m-1 −CH ₃ , −O− (CH ₂ ) _m-2 −CH ₃ , −S− (CH ₂ ) _m-2 −CH ₃ , −NH− (CH ₂ ) _m-2 −CH ₃ , −N (− (CH ₂ ) _m-2 −CH ₃ ) − (CH ₂ ) _m'-2 −CH ₃ , −O (C = O) − (CH ₂₎ ) _M-3 −CH ₃ , −C (= O) O− (CH ₂ ) _m-3 −CH ₃ , and so on. Among these, − (CH ₂ ) _m-1 −CH ₃ and −O− (CH ₂ ) _m-2 −CH ₃ are preferable from the viewpoint of enhancing the molecular orientation of the liquid crystal compound. Here, m and m'are integers.

Examples of the alkyl group in the above-mentioned chain organic group include a linear or branched alkyl group, and the carbon-carbon bond of the alkyl group may be partially unsaturated and alkyl. One or more methylene groups contained in the group are ether oxygen atom, thioether sulfur atom, amine nitrogen atom (-NH-, -N (RA)-: where RA has 1 to 1 carbon atoms. Represents a linear or branched alkyl group of 6), carbonyl group, ester bond, amide bond, -CHF-, -CF _2- , -CHCl-, -CCl _2- replaced (displace). It may be a structure.
As the alkyl group in these chain organic groups, since the molecular linearity is high, a part of the carbon of the alkyl group may be an unsaturated bond, and one or more contained in the alkyl group. The methylene group is preferably a linear alkyl group, which may have a structure in which the above-mentioned group is substituted (displace).
The chain length of the branched organic group is the longest of the branches. The chain length of the replaced chain organic group also includes the atom of the replaced bond in the number. As an example,-(CH ₂ ) _m-1 -CH ₃ , -O- (CH ₂ ) _m-2 -CH ₃ , -S- (CH ₂ ) _m-2 -CH ₃ , -NH- (CH ₂ ) _{The chain length of m-2} −CH ₃ , −O (C = O) − (CH ₂ ) _m-3 −CH ₃ , −C (= O) O− (CH ₂ ) _m-3 −CH ₃ is an integer m. It becomes. Further, the chain length of −N (− (CH ₂ ) _m1-2 −CH ₃ ) − (CH ₂ ) _m2-2 −CH ₃ is the larger value among the integers m1 and m2.

Among the above, the chain length of the non-polymerizable chain organic group is 6 or more, and a linear or branched alkyl group is preferable from the viewpoint of molecular orientation of the liquid crystal compound. The carbon-carbon bond of the alkyl group may be partially unsaturated, and one or more methylene groups contained in the alkyl group may be an ether oxygen atom or a thioether sulfur atom. It may be replaced with an amine nitrogen atom, a carbonyl group, an ester bond, an amide bond, -CHF-, -CF2-, -CHCl-, -CCl2-.

One of R1 and R2 is a chain organic group having a polymerizable group. In R1 or R2, the position and number of the polymerizable groups are not particularly limited, but 1 to 3 polymerizable groups may be substituted, and in particular, one polymerizable group is substituted for the liquid crystal during polymerization. It is preferable because it does not inhibit the molecular orientation of the compound. In particular, it is more preferable that one polymerizable group is substituted at the end of the alkyl group of the above-mentioned chain organic group because it does not inhibit the molecular orientation of the liquid crystal compound and a high degree of polymerization can be easily obtained. Further, it is more preferable that one polymerizable group is substituted only at the terminal of the above-mentioned chain organic group because the molecular symmetry of the liquid crystal compound is good and the molecular arrangement is facilitated.

A polymerizable group 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. The polymerizable group is preferably a photopolymerizable group from the viewpoint of producing an anisotropic dye film.
Examples of the polymerizable group include acryloyl group, metaacryloyl group, acryloyloxy group, metaacryloyloxy group, acryloylamino group, metaacryloylamino group, vinyl group, vinyloxy group, ethynyl group, ethynyloxy group, 1,3-. Examples include butazienyl group, 1,3-butadienyloxy group, oxylanyl group, oxetanyl group, glycidyl group, glycidyloxy group, styryl group, styryloxy group, etc., and include acryloyl group, metaacryloyl group, acryloyloxy group, metaacryloyl. Oxy group, acryloyl amino group, metaacryloylamino group, oxylanyl group, glycidyl group, glycidyloxy group are preferable, and acryloyl group, metaacryloyl group, acryloyloxy group, metaacryloyloxy group, acryloylamino group, metaacryloylamino group, glycidyl. Groups and glycidyloxy groups are more preferable, and acryloyloxy groups, metaacryloyloxy groups, and glycidyloxy groups are even more preferable.

Specific examples of the chain organic group having a polymerizable group include − (CH ₂ ) _n − polymerizable group.
−O− (CH ₂ ) _n-1 −polymerizable group,
− (O) _n1 − (CH ₂ CH ₂ O) _n2 − (CH ₂ ) _n3 − polymerizable group,
− (O) _n1 − (CH ₂ ) _n3 − (CH ₂ CH ₂ O) _n2 − polymerizable group,
Is preferable from the viewpoint of molecular orientation of the liquid crystal compound.
Further, among these, − (CH ₂ ) _n − polymerizable group and −O − (CH ₂ ) _n-1 − polymerizable group are preferable, and n is particularly preferably 3 or more. By the above, there is a tendency to improve the molecular orientation of the liquid crystal compound and suppress defects.
In addition, n in these formulas represents an integer, and the chain length in a chain organic group means the longest chain portion in a chain organic group, and the chain organic group is substituted with a polymerizable group. If so, it means the longest chain portion in the portion excluding the polymerizable group.) The number of atoms is n. Further, n1, n2, and n3 in the above equation independently represent integers, and the chain length in the chain organic group means the longest chain portion in the chain organic group, and the chain organic group. When is substituted with a polymerizable group, it means the longest chain portion in the portion excluding the polymerizable group), and the number of atoms is n1 + 3 * n2 + n3.

The chain length n and the chain length n1 + 3 * n2 + n3 are preferably 1 or more, more preferably 2 or more, still more preferably 3 or more, still more preferably 6 or more, particularly preferably 7 or more, and particularly more preferably. Is 8 or more. Further, it is preferably 20 or less, more preferably 15 or less, further preferably 14 or less, particularly preferably 12 or less, and particularly more preferably 10 or less. When it is equal to or more than the above lower limit, the liquid crystal property is exhibited, the effect of lowering the isotropic phase development temperature, and the effect of imparting mechanical strength by polymerization tend to be obtained. There is a tendency to obtain the effect of suppressing defects during the formation of a dye film.

The chain length of the chain organic group having a polymerizable group will be specifically described in a preferable form in the case where only one polymerizable group is provided at the end of the following chain organic group having a polymerizable group.
― (CH ₂ ) _n ― CH = CH, ―O― (CH ₂ ) _n-1 ―CH = CH, − (CH ₂ ) _n-1 −O−CH = CH, −O− (CH ₂ ) _{n- 2-} O-CH = CH,-(CH ₂ ) _n-2 -O- (C = O) -CH = CH, -O- (CH ₂ ) _n-3 -O- (C = O) -CH = CH,

In these formulas, n represents an integer, and the chain length of the chain organic group having a polymerizable group is n.

When X and R1 or X and R2 are bonded as in the formulas (1B) and (1E), for example, when A3 is a single bond in the formula (1B) or when A1 is a single bond in the formula (1E). When R1 or R2 is bonded to Y1 or Y2 as in the case of a single bond, R1 or R2 bonded to X or Y1 or Y2 is polymerizable from the viewpoint of enhancing the molecular orientation of the liquid crystal compound. It is preferably − (CH ₂ ) _m-1 −CH ₃ that may be substituted with a group, and more preferably _{− (CH 2} ) _m-1 −CH _{3 substituted with a polymerizable group.}
Further, as described above, R1 or R2 which does not bind to X or Y1 or Y2 may be substituted with a polymerizable group from the viewpoint of enhancing the molecular orientation of the liquid crystal compound-O- (CH ₂ ) _m-. is preferably ₂ -CH _3, has been -O- (CH ₂₎ substituted with a polymerizable group is more preferably a _m-2 -CH _3.

(Y1 and Y2)
-Y1- and -Y2- are independently single-bonded, -C (= O) O-, -OC (= O)-, -C (= S) O-, -OC (= S)-, respectively. -C (= O) S-, -SC (= O)-, -CH ₂ CH _2- , -CH = CH-, -C (= O) NH-, -NHC (= O)-, -CH ₂ Represents O-, -OCH _2- , -CH ₂ S-, or -SCH _2-.
With these structures, the linearity of the liquid crystal compound and the rotational movement around the short axis of the molecule tend to be easy, and the above structure having a small π bond property is suitable. Among these, since the above tendency is further observed, single bond, -C (= O) O-, -OC (= O)-, -CH ₂ CH _2- , -CH ₂ O- or -OCH _2- preferable.

When X and Y1 or X and Y2 are bonded as in the formula (1A), the formula (1C), the formula (1D), and the formula (1F), the Y1 that binds to X or the Y2 that binds to X Is preferably a single bond from the viewpoint of the linearity of the liquid crystal compound, and the other of -X- and -Y1- and -Y2- is -C (= O) O- or -OC (= O)-. Is preferable.
Further, when X is not bound to either Y1 or Y2 as in the formulas (1B) and (1E), -X- is-from the viewpoint of the rotational movement of the liquid crystal compound around the molecular minor axis. CH ₂ CH ₂ −, −CH ₂ O−, or −OCH ₂₋ ; both −Y1- and −Y2- are −C (= O) O− or −OC (= O) − Is preferable.

As the formula (1), the above formula (1A), the above formula (1B), the above (1E), and the above (1F) are preferable from the viewpoint of lowering the isotropic phase expression temperature and increasing the molecular orientation.

Specifically, the following compounds can be mentioned as the formula (1), but the present invention is not limited thereto.

The liquid crystal compound contained in the composition for forming an anisotropic dye film of the present invention preferably comprises the liquid crystal compound represented by the above formula (1). Here, the liquid crystal compound contained in the composition for forming an anisotropic dye film of the present invention may be one kind of the liquid crystal compound represented by the above formula (1), or two or more kinds may be used in combination. Further, a liquid crystal compound other than the crystal compound represented by the formula (1) may be used in combination.

From the viewpoint of the process, the liquid crystal compound contained in the composition for forming an anisotropic dye film of the present invention preferably has an isotropic phase appearance temperature of generally less than 200 ° C and less than 160 ° C. , Less than 140 ° C., more preferably less than 130 ° C., even more preferably less than 115 ° C., particularly preferably less than 110 ° C., and particularly preferably less than 105 ° C.
Here, the isotropic phase appearance temperature means the phase transition temperature from the liquid crystal to the liquid and the phase transition temperature from the liquid to the liquid crystal. In the present invention, at least one of these phase transition temperatures is preferably in the above range, and more preferably both of these phase transition temperatures are in the above range.

The liquid crystal compound contained in the composition for forming an anisotropic dye film of the present invention includes an alkylation reaction, an esterification reaction, an amidation reaction, an etherification reaction, an ipso substitution reaction, a coupling reaction using a metal catalyst, and the like. It can be produced by combining known chemical reactions.
For example, the liquid crystal compound contained in the composition for forming an anisotropic dye film of the present invention includes the method described in Examples and 449 of "Liquid Crystal Handbook" (Maruzen Co., Ltd., published on October 30, 2000). It can be synthesized according to the method described on page 468.

<Dye>
In the present invention, the dye is a substance or compound that absorbs at least a part of wavelengths in the visible light region (380 nm to 780 nm).
Examples of the dye that can be used in the present invention include a dichroic dye. The dichroic dye refers to a dye having a property in which the absorbance in the major axis direction and the absorbance in the minor axis direction of the molecule are different. Further, the dye may be a dye having a liquid crystal property or may not have a liquid crystal property. In addition, having liquid crystal property means that the liquid crystal phase is expressed at an arbitrary temperature.

The dyes contained in the composition for forming an anisotropic dye film of the present invention include azo dyes, quinone dyes (including naphthoquinone dyes, anthraquinone dyes, etc.), stilben dyes, cyanine dyes, and phthalocyanines. Examples thereof include system dyes, indigo dyes, condensed polycyclic dyes (including perylene dyes, oxazine dyes, acrydin dyes, etc.) and the like. Among these dyes, azo dyes are preferable because they have a large molecular length-minor axis ratio and can have a high molecular arrangement in an anisotropic dye film.
The azo dye refers to a dye having at least one azo group (-N = N-), and the number of azo groups in one molecule is solubility in a solvent, compatibility with a liquid crystal compound, and color tone. From the viewpoint of ease of production, 1 or more is preferable, 2 or more is more preferable, 6 or less is preferable, 4 or less is more preferable, and 3 or less is further preferable.

Examples of the azo dye include a compound represented by the formula (A). The dye represented by the formula (A) has good compatibility with the liquid crystal compound represented by the formula (1), and is good when mixed with the liquid crystal compound represented by the formula (1). Indicates the color ratio.

R11-D1-N = N- (D2-N = N) _p- D3-R12 ... (A)

In formula (A),
D1, D2 and D3 are each independently a phenylene group which may have a substituent, a naphthylene group which may have a substituent, or a divalent heterocycle which may have a substituent. Represents a group;
p represents an integer from 0 to 4;
If p is an integer greater than or equal to 2, multiple D2s may be the same or different from each other;
R11 and R12 represent the same or different monovalent organic groups.

D1, D2 and D3 are each independently a phenylene group which may have a substituent, a naphthylene group which may have a substituent, or a divalent heterocycle which may have a substituent. Represents a group.
As the substitution position of the phenylene group, a 1,4-phenylene group is preferable because the linearity of the molecule is high.
As the substitution position of the naphthylene group, a 1,4-naphthylene group or a 2,6-naphthylene group is preferable because of the high linearity of the molecule.

As the divalent heterocyclic group, the number of carbon atoms forming the ring is preferably 3 or more and 14 or less, and more preferably 10 or less. In particular, monocyclic or bicyclic heterocyclic groups are preferable.
Examples of the atom other than carbon constituting the divalent heterocyclic group include at least one selected from a nitrogen atom, a sulfur atom and an oxygen atom. When the heterocyclic group has a plurality of atoms constituting a ring other than carbon, they may be the same or different.
Specifically, a pyridinediyl group, a quinolinediyl group, an isoquinolindiyl group, a thiazolediyl group, a benzothiazolediyl group, a thienothiazolediyl group, a thienothiophendiyl group, a benzimidazolidinonediyl group, a benzofuranyl group, a phthalimidediyl group, Examples thereof include an oxazolediyl group and a benzoxazolediyl group.

The substituents optionally contained in the phenylene group, naphthylene group, and divalent heterocyclic group in D1, D2, and D3 are alkyl groups having 1 to 4 carbon atoms; Alkax group of ~ 4; Alkyl fluoride group having 1 to 4 carbon atoms such as trifluoromethyl group; Cyano group; Nitro group; Hydroxyl group; Halogen atom; Substituent or unsubstituted amino such as amino group, diethylamino group, and pyrrolidino group A group (a substituted amino group is an amino group having one or two alkyl groups having 1 to 4 carbon atoms, or two substituted alkyl groups are bonded to each other to form an alcandiyl group having 2 to 8 carbon atoms. The unsubstituted amino group is −NH ₂ , and examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group and a butyl group. The alkyl group has 2 to 8 carbon atoms. As the alcandiyl group, ethylene group, propane-1,3-diyl group, butane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1, 6-Diyl group, heptane-1,7-diyl group, octane-1,8-diyl group and the like can be mentioned.)
From the point of high molecular linearity, when it is unsubstituted or substituted, it is substituted with a methyl group, a methoxy group, a hydroxyl group, a fluorine atom, a chlorine atom, a dimethylamino group, a pyrrolidinyl group, or a piperidinyl group. Is preferable.

p represents an integer from 0 to 4. From the viewpoint of solubility in a solvent, compatibility with a liquid crystal compound, color tone, and ease of production, 1 or more is preferable, 4 or less is preferable, and 3 or less is more preferable.

R11 and R12 represent the same or different monovalent organic groups.
The monovalent organic group in R11 and R12 includes a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a branch; an alicyclic alkyl group having 1 to 20 carbon atoms; a methoxy group and an ethoxy group. And an alkoxy group having 1 to 20 carbon atoms which may have a branch such as a butoxy group; an alkyl fluoride group having 1 to 20 carbon atoms which may have a branch such as a trifluoromethyl group; a cyano group; Nitro group; hydroxyl group; halogen atom; substituted or unsubstituted amino group such as amino group, diethylamino group, and pyrrolidino group (Substituted amino group is an alkyl group having 1 to 20 carbon atoms which may have a branch. It means an amino group having one or two, or an amino group in which two substituted alkyl groups are bonded to each other to form an alcandiyl group having 2 to 20 carbon atoms. The unsubstituted amino group is -NH ₂ . Examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group and a butyl group. Examples of the alcandiyl group having 2 to 20 carbon atoms include an ethylene group and a propane-1,3-diyl group. , Butane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1, 8-Diyl group and the like.); Carboxy group; may have a branch such as a butoxycarbonyl group; an alkyloxycarbonyl group having 1 to 20 carbon atoms; may have a branch such as an ethenyl group. Alkenyl group having 1 to 20 carbon atoms; Alkylphenylalkenyl group such as 2- (4-butylphenyl) ethenyl group; Carbamoyl group; Alkylcarbamoyl having 1 to 20 carbon atoms which may have a branch such as a butylcarbamoyl group. Group; Sulfamoyl group; Alkyl sulfamoyl group having 1 to 20 carbon atoms which may have a branch such as a butyl sulfamoyl group; 1 to 1 carbon atoms which may have a branch such as a butylcarbonylamino group. An acylamino group of 20; an acyloxy group having 1 to 20 carbon atoms which may have a branch such as a butylcarbonyloxy group; a sulfanyl group; an alkylsulfanyl group having 1 to 20 carbon atoms such as a butylsulfanyl group; a liquid crystal described later. Examples thereof include a chain organic group having a polymerizable group of R1 and R2 in the compound.

R11 and R12 include hydrogen atoms, chain groups, aliphatic organic groups (“aliphatic organic groups” include chain and cyclic groups), and part of the carbon is nitrogen and / or oxygen. Substituted aliphatic organic groups (“Adioxyorganic groups in which a part of carbon is replaced with nitrogen and / or oxygen” includes chain-like and cyclic ones, and methyl of some of the aliphatic organic groups. (Including those in which the group is replaced with a hydroxyl group, an oxo group (= O), an amino group, an imino group, etc.) and the like. In one embodiment, a hydrogen atom and a chain group are preferable, and in another embodiment, a hydrogen atom and a chain group are preferable. Is preferably a hydrogen atom or an aliphatic organic group, and in still another embodiment, a hydrogen atom or an aliphatic organic group in which a part of carbon is replaced with nitrogen and / or oxygen is preferable.

As the chain group, the above-mentioned alkyl group having 1 to 20 carbon atoms which may have a branch; an alkoxy group having 1 to 20 carbon atoms which may have a branch; may have a branch. A good alkyl fluoride group having 1 to 20 carbon atoms; a substituted or unsubstituted amino group (a substituted amino group is an amino group having one or two alkyl groups having 1 to 20 carbon atoms which may have a branch. The substituent (unsubstituted amino group is -NH ₂ ); carboxy group; may have a branch alkyloxycarbonyl group having 1 to 20 carbon atoms; carbamoyl group; even if it has a branch. A good alkylcarbamoyl group having 1 to 20 carbon atoms; a sulfamoyl group; an alkylsulfamoyl group having 1 to 20 carbon atoms which may have a branch; an acylamino group having 1 to 20 carbon atoms which may have a branch. An acyloxy group having 1 to 20 carbon atoms which may have a branch; a sulfanyl group; an alkylsulfanyl group having 1 to 20 carbon atoms and the like can be mentioned.

Examples of the aliphatic organic group include the above-mentioned alkyl group having 1 to 20 carbon atoms which may have a branch, an alicyclic alkyl group having 1 to 20 carbon atoms, and the like.
As the aliphatic organic group in which a part of carbon is replaced with nitrogen and / or oxygen, the above-mentioned alkoxy group having 1 to 20 carbon atoms which may have a branch; a substituted or unsubstituted amino group (substituted amino) A group is an amino group having one or two alkyl groups having 1 to 20 carbon atoms which may have a branch, or an alkanediyl group having 2 to 20 carbon atoms in which two substituted alkyl groups are bonded to each other. The unsubstituted amino group is −NH ₂ , and examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group and a butyl group. Examples of the alkanediyl group having the number 2 to 20 include an ethylene group, a propane-1,3-diyl group, a butane-1,3-diyl group, a butane-1,4-diyl group, and a pentane-1,5-diyl group. Examples include hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, etc.); Carboxy group; 1 to 20 carbon atoms which may have a branch. Alkyloxycarbonyl group; Carbamoyl group; May have a branched alkylcarbamoyl group with 1 to 20 carbon atoms; May have a branched acylamino group with 1 to 20 carbon atoms; Even if it has a branch Examples thereof include an acyloxy group having 1 to 20 carbon atoms.

R11 and R12 are independent of each other because of their high molecular linearity, that is, a hydrogen atom or an alkyl group having 1 to 10 carbon atoms such as a butyl group, a pentyl group, a hexyl group, a heptyl group and an octyl group; a butoxy group. , Pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group and other alkoxy groups having 1 to 10 carbon atoms, diethylamino group, pyrrolidino group and piperidinyl group are preferably substituted. Further, a chain organic group having a polymerizable group of R1 and R2 in the above-mentioned liquid crystal compound is also preferable.

The dye contained in the composition for forming an anisotropic dye film of the present invention is not particularly limited, and a known dye can also be used.
Known dyes include, for example, the dyes described in Patent Document 1, Japanese Patent No. 5982762, Japanese Patent Application Publication No. 2017-025317, and Japanese Patent Application Publication No. 2014-095899. Bicolor dyes, bicolor dyes) can be mentioned.

Specific examples thereof include, but are not limited to, the dyes described below.

The molecular weight of the dye contained in the composition for forming an anisotropic dye film of the present invention is preferably 300 or more, more preferably 350 or more, further preferably 380 or more, further preferably 1500 or less, and even more preferably 1200 or less. 1000 or less is more preferable. Specifically, the molecular weight of the dye contained in the composition for forming an anisotropic dye film of the present invention is preferably 300 to 1500, more preferably 350 to 1200, and even more preferably 380 to 1000.

The content of the dye (dichroic dye) in the anisotropic dye film forming composition is, for example, 0.01 with respect to the solid content (100 parts by mass) of the anisotropic dye film forming composition. It is preferably parts by mass or more, more preferably 0.05 parts by mass or more, preferably 30 parts by mass or less, and more preferably 10 parts by mass or less. Specifically, the content of the dye (dichroic dye) in the anisotropic dye film forming composition is, for example, relative to the solid content (100 parts by mass) of the anisotropic dye film forming composition. It is 0.01 to 30 parts by mass, preferably 0.05 to 10 parts by mass.
When the content occupied by the dye (dichroic dye) is within the above range, the anisotropic dye of the present invention is not disturbed without disturbing the orientation of the liquid crystal compound contained in the composition for forming an anisotropic dye film of the present invention. There is a tendency that the compound contained in the film-forming composition can be polymerized. Further, when the content occupied by the dye (dichroic dye) is at least the above lower limit value, sufficient light absorption tends to be obtained and sufficient polarization performance tends to be obtained. Further, when the content occupied by the dye (dichroic dye) is not more than the above upper limit value, the inhibition of the orientation of the liquid crystal molecules tends to be suppressed easily.
Depending on the purpose, the dye (dichroic dye) may be used alone or in combination of two or more.

<Solvent>
The composition for forming an anisotropic dye film of the present invention may contain a solvent, if necessary.
The solvent that can be used is not particularly limited as long as it can sufficiently disperse or dissolve the dye or other additives in the liquid crystal compound, and for example, methanol, ethanol, ethylene glycol, isopropyl alcohol, propylene glycol, ethylene. Alcohol solvents such as 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; acetone, methyl ethyl ketone, Ketone solvents such as cyclopentanone, cyclohexanone, 2-heptanone, methylisobutylketone; aliphatic hydrocarbon solvents such as pentane, hexane and heptane; aromatic hydrocarbon solvents such as toluene and xylene; nitrile solvents such as acetonitrile; tetrahydrofuran, Ether solvents such as dimethoxyethane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether; fluorine-containing solvents such as perfluorobenzene, perfluorotoluene, perfluorodecalin, perfluoromethylcyclohexane, hexafluoro-2-propanol; and chloroform, dichloromethane, chlorobenzene, di A chlorine-containing solvent such as chlorobenzene; can be mentioned.
Only one type of these solvents may be used, or two or more types may be used in combination.

The solvent is preferably a solvent capable of dissolving the liquid crystal compound and the dye, and more preferably a solvent in which the liquid crystal compound and the dye are completely dissolved. When the liquid crystal compound is a polymerizable compound, it is preferably a solvent that is inert to the polymerization reaction. Further, from the viewpoint of applying the composition for forming an anisotropic dye film of the present invention, a solvent having a boiling point in the range of 50 to 200 ° C. is preferable.

When the composition for forming an anisotropic dye film of the present invention contains a solvent, the content ratio of the solvent in the composition for forming an anisotropic dye film is the total amount (100% by mass) of the composition of the present invention. Therefore, 50 to 98% by mass is preferable. In other words, the solid content in the composition for forming an anisotropic dye film of the present invention is preferably 2 to 50% by mass.
When the solid content in the anisotropic dye film forming composition is not more than the above upper limit value, the viscosity of the anisotropic dye film forming composition does not become too high, and the thickness of the obtained polarizing film becomes uniform. , The polarizing film tends to be less likely to be uneven.
The solid content can be determined in consideration of the thickness of the polarizing film to be produced.
The viscosity of the composition for an anisotropic dye film of the present invention is not particularly limited as long as a uniform film having no uneven thickness is produced by the coating method described later, but the thickness uniformity over a large area, the coating speed, and the like are not particularly limited. From the viewpoint of obtaining in-plane uniformity of productivity and optical characteristics, 0.1 mPa · s or more is preferable, 500 mPa · s or less is preferable, 100 mPa · s or less is more preferable, and 50 mPa · s or less is further preferable.

<Other additives>
The composition for forming an anisotropic dye film of the present invention further comprises a polymerizable liquid crystal compound other than the liquid crystal compound represented by the formula (1) and a liquid crystal compound other than the liquid crystal compound represented by the formula (1), if necessary. Non-polymerizable liquid crystal compounds, polymerization initiators, polymerization inhibitors, polymerization aids, polymerizable non-liquid crystal compounds, surfactants, leveling agents, coupling agents, pH adjusters, dispersants, antioxidants, organic / inorganic Other additives such as fillers, organic / inorganic nanosheets, organic / inorganic nanofibers, metal oxides and the like may be contained. By containing an additive, the coatability and stability of the anisotropic dye film forming composition can be improved, and the stability of the anisotropic dye film formed from the anisotropic dye film forming composition can be improved. May be improved.

[Method for Producing Composition for Anisotropic Dye Film Formation]
The method for producing the composition for an anisotropic dye film of the present invention is not particularly limited. For example, a dye, a liquid crystal compound, a solvent, other additives and the like are mixed, and the dye is dissolved by stirring and shaking at 0 to 80 ° C. In the case of poor solubility, a homogenizer, a bead mill disperser, or the like may be used.
As a method for producing the composition for an anisotropic dye film of the present invention, a filtration step may be provided for the purpose of removing foreign substances and the like in the composition.
In the composition for forming an anisotropic dye film of the present invention, the composition obtained by removing the solvent from the composition for forming an anisotropic dye film may or may not be a liquid crystal at an arbitrary temperature, but at an arbitrary temperature. It is preferable to show liquid crystallinity. The composition obtained by removing the solvent from the composition for forming an anisotropic dye film has an isotropic phase appearance temperature of generally less than 200 ° C. and less than 160 ° C. from the viewpoint of the coating process described below. It is preferably less than 140 ° C, more preferably less than 130 ° C, even more preferably less than 115 ° C, particularly preferably less than 110 ° C, and particularly preferably less than 105 ° C.

[Anisotropic dye film]
The anisotropic dye film of the present invention contains a dye and a liquid crystal compound represented by the above formula (1).
The anisotropic dye film of the present invention comprises a polymerizable liquid crystal compound other than the liquid crystal compound having a partial structure represented by the above formula (1), a non-polymerizable liquid crystal compound, a polymerization initiator, a polymerization inhibitor, a polymerization aid, and the like. Polymerizable non-liquid crystal compound, non-polymerizable non-liquid crystal compound, surfactant, leveling agent, coupling agent, pH adjuster, dispersant, antioxidant, organic / inorganic filler, organic / inorganic nanosheet, organic / inorganic nanofiber , Metal oxides and the like may be included.
The anisotropic dye film of the present invention can be formed by using the composition for forming an anisotropic dye film of the present invention.

The anisotropic dye film in the present invention can function as a polarizing film for obtaining linearly polarized light, circularly polarized light, elliptically polarized light, etc. by utilizing the anisotropy of light absorption, and also has a film forming process and a substrate or an organic compound (dye). By selecting a composition containing (or transparent material), it is possible to function as various anisotropic dye films such as refractive anisotropy and conduction anisotropy.

When the anisotropic dye film of the present invention is used as a polarizing element for an antireflection film for a liquid crystal display or an OLED, the orientation characteristic of the anisotropic dye film can be expressed by using a two-color ratio. When the two-color ratio is 8 or more, it functions as a polarizing element, but 15 or more is preferable, 20 or more is more preferable, 25 or more is further preferable, 30 or more is particularly preferable, and 40 or more is particularly preferable. Further, the higher the two-color ratio, the more preferable. When the two-color ratio is at least the above lower limit value, it is useful as an optical element described later, particularly a polarizing element.
When used as a polarizing element of an antireflection film for OLED, even if the performance of a peripheral material such as a retardation film is low, if the performance of the polarizing element is high, the characteristics as an antireflection film are improved. Therefore, if the performance of the polarizing element is high, the layer structure can be easily simplified, sufficient functions can be easily exhibited even in a thin film structure, and the polarizing element can be suitably used for applications including folding and bending. In addition, the cost can be kept low.

The two-color ratio (D) referred to 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 the light incident on the anisotropic dye film is parallel to the orientation direction of the anisotropic dye, and Ay is the polarization of the light incident on the anisotropic dye film. Absorbance observed when the direction is perpendicular.
The absorbance of each of them is not particularly limited as long as it has the same wavelength, and any wavelength may be selected depending on the purpose. However, when expressing the degree of orientation of the anisotropic dye film, it is 380 nm of the anisotropic dye film. It is preferable to use a value corrected by visual sensitivity in a specific wavelength range of about 780 nm or a value in the maximum absorption wavelength in the visible range.

The transmittance of the anisotropic dye film of the present invention in the visible light wavelength region is preferably 25% or more, more preferably 35% or more, and particularly preferably 40% or more. Further, the transmittance may be an upper limit according to the application. For example, when the degree of polarization is increased, the transmittance is preferably 50% or less. Having a transmittance in the above range, it is useful as an optical element to be described later, and as an optical element for a liquid crystal display used for color display or an antireflection film in which an anisotropic dye film and a retardation film are combined. It is useful.

The thickness of the anisotropic dye film is preferably 10 nm or more, more preferably 100 nm or more, and further preferably 500 nm or more as a dry film thickness. On the other hand, it is preferably 30 μm or less, more preferably 10 μm or less, still more preferably 5 μm or less, and particularly preferably 3 μm or less. When the thickness of the anisotropic dye film is within the above range, it tends to be possible to obtain a uniform orientation and a uniform film thickness of the dye in the film.

[Manufacturing method of anisotropic dye film]
The anisotropic dye film of the present invention is preferably produced by a wet film forming method using the composition for forming an anisotropic dye film of the present invention.
The wet film forming method referred to in the present invention is a method of applying and orienting an anisotropic dye film composition on a substrate by some method. Therefore, the composition for an anisotropic dye film may or may not contain a solvent as long as it has fluidity. From the viewpoint of viscosity and film uniformity at the time of coating, it is more preferable to contain a solvent.
The orientation of the liquid crystal or the dye in the anisotropic dye film may be oriented by shearing or the like in the coating process, or may be oriented in the process of drying the solvent. Further, the liquid crystal, the dye, etc. may be oriented and laminated on the substrate through a process of reorienting the liquid crystal, the dye, or the like by heating after coating and drying. In the wet film formation method, when the composition for an anisotropic dye film is applied onto a substrate, it is already in the composition for an anisotropic dye film, in the process of drying the solvent, or after the solvent is completely removed. Then, the dye or the liquid crystal compound undergoes self-association (molecular association state such as liquid crystal state), so that orientation occurs in a minute area. By giving an external field to this state, it is possible to obtain an anisotropic dye film having desired performance by orienting in a certain direction in a macro region. In this respect, it is different from the method based on the principle that a polyvinyl alcohol (PVA) film or the like is dyed with a solution containing a dye, stretched, and the dye is oriented only by a stretching step. Here, the external field includes the influence of the alignment treatment layer previously applied on the substrate, shearing force, magnetic field, electric field, heat, etc., and these may be used alone or in combination of two or more. Good. If necessary, a heating step may be performed.

The process of applying the composition for an anisotropic dye film on the substrate to form a film, the process of applying an external field to align the composition, and the process of drying the solvent may be performed sequentially or at the same time.

Examples of the method of applying the anisotropic dye film forming composition on the substrate in the wet film forming method include a coating method, a dip coating method, an LB film forming method, and a known printing method. There is also a method of transferring the anisotropic dye film thus obtained to another substrate.

Among these, it is preferable to apply the composition for forming an anisotropic dye film onto the substrate by 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 is, for example, the transmission axis (polarization axis) or absorption axis of polarized light in the case of a polarizing film, and the phase advance axis in the case of a retardation film. Or it is the slow axis.

The method for applying the composition for an anisotropic dye film to obtain an anisotropic dye film is not particularly limited, but for example, "Coating Engineering" by Yuji Harasaki (Asakura Shoten Co., Ltd., published on March 20, 1971). ), Pages 253 to 277, "Creation and application of molecular coordinating materials" supervised by Kunihiro Ichimura (CMC Publishing Co., Ltd., published on March 3, 1998), methods described on pages 118 to 149, steps. Slot die coating method, spin coating method, spray coating method, bar coating method, roll coating method, blade coating method, curtain coating method, fountain method, dip method, etc. on a substrate having a structure (orientation treatment may be performed in advance). The method of applying with is mentioned. Of these, the slot die coating method and the bar coating method are preferable because an anisotropic dye film having high uniformity can be obtained.

The die coater used in the slot die coating method generally includes a coating machine that discharges a coating liquid, a so-called slit die. Slit dies are used, for example, in Japanese Patent Application Laid-Open No. 2-164480, Japanese Patent Application Laid-Open No. 6-154678, Japanese Patent Application Laid-Open No. 9-131559, "Basics and Applications of Dispersion / Coating / Drying" (2014). , Technosystem Co., Ltd., ISBN97849247228707 C 305), "Wet coating technology in display and optical components" (2007, Information Organization, ISBN9784901677752), "Precision coating and drying technology in the electronics field" (2007, Technical Information Association, ISBN9784861041389) ) Etc. are disclosed. These known slit dies can be applied even to a flexible member such as a film or tape or a hard member such as a glass substrate.

As the substrate used for forming the anisotropic dye film of the present invention, glass, triacetate, acrylic, polyester, polyimide, polyetherimide, polyetheretherketone, polycarbonate, cycloolefin polymer, polyolefin, polyvinyl chloride, triacetyl Examples thereof include cellulose or urethane films. Further, on the surface of this substrate, in order to control the orientation direction of the dye, a known method (rubbing) described on pages 226 to 239 of "LCD Handbook" (Maruzen Co., Ltd., published on October 30, 2000). Method, method of forming a groove (fine groove structure) on the surface of the alignment film, method of using polarized ultraviolet light / polarized laser (photoalignment method), orientation method by LB film formation, orientation method by diagonal deposition of inorganic substances, etc.) Therefore, the alignment treatment (alignment film) may be applied. In particular, orientation treatment by a rubbing method or a photo-alignment method can be preferably mentioned. Examples of the material used in the rubbing method include polyvinyl alcohol (PVA), polyimide (PI), epoxy resin, acrylic resin and the like. Examples of the material used in the photoalignment method include polycinnamate type, polyamic acid / polyimide type, and azobenzene type. When the alignment treatment layer is provided, it is considered that the liquid crystal compound and the dye are oriented due to the influence of the alignment treatment of the alignment treatment layer and the shearing force applied to the composition for the anisotropic dye film at the time of coating.

When the composition for the anisotropic dye film is applied, the supply method and the supply interval of the composition for the anisotropic dye film are not particularly limited. Since the coating liquid supply operation may become complicated and the coating film thickness may fluctuate at the start and stop of the coating liquid, it is continuously anisotropic when the thickness of the anisotropic dye film is thin. It is desirable to apply the composition for a sex dye film while supplying it.

The speed at which the composition for an 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, still more preferable. Is 1.0 m / min or more, and particularly preferably 5.0 m / min or more. Further, it is usually 400 m / min or less, preferably 200 m / min or less, more preferably 100 m / min or less, and further preferably 50 m / min or less. When the coating rate is in the above range, the anisotropy of the anisotropic dye film can be obtained, and the coating tends to be uniform.
The coating temperature of the composition for an anisotropic dye film 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 at the time of coating the composition for an anisotropic dye film is preferably 10% RH or more, and preferably 80 RH or less.

The anisotropic dye film may be insolubilized. The insolubilization means a treatment of controlling the elution of the compound from the anisotropic dye film by reducing the solubility of the compound in the anisotropic dye film and enhancing the stability of the film.
Specifically, film polymerization, overcoating, and the like are preferable from the viewpoints of ease of post-process, durability of the anisotropic dye film, and the like.

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

When the 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, but for example, a xenon lamp, a halogen lamp, a tungsten lamp, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, a metal halide lamp, a medium pressure mercury lamp, a low pressure mercury lamp, and carbon. Lamp light sources such as arcs and fluorescent lamps; laser light sources such as argon ion lasers, YAG lasers, excima lasers, nitrogen lasers, helium cadmium lasers, and semiconductor lasers can be mentioned. An optical filter can also be used when irradiating light of a specific wavelength for use. The exposure amount of the active energy ray ^{is preferably 1 to 100,000 J / m 2} , more preferably 10 to 10,000 J / m ^2.

When the polymerization is carried out using heat, it is preferably carried out in the range of 50 to 200 ° C., and more preferably carried out in the range of 60 to 150 ° C.
Polymerization may be carried out using light, heat, and / or radiation, but it is preferable to use photopolymerization or to use photopolymerization and thermal polymerization in combination because the film forming process takes a short time and the apparatus is simple. Is preferable.

[Optical element]
The optical element of the present invention includes the anisotropic dye film of the present invention.
The optical element in the present invention has functions such as a polarizing element for obtaining linearly polarized light, circularly polarized light, elliptically polarized light, retarded polarization, a retardation element, refractive anisotropy, conduction anisotropy, etc. Represents an element. These functions can be appropriately adjusted by the anisotropic dye film forming process and the selection of a composition containing a substrate or an 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 another layer in order to maintain and improve the function of the anisotropic dye film. For example, a layer having a function of blocking a specific wavelength or a layer having a function of blocking a specific substance (oxygen blocking film, steam blocking film, etc.) used to improve durability such as light resistance, heat resistance, and water resistance. Barrier film, etc.); A wavelength cut filter or a layer containing a material that absorbs a specific wavelength, which is used for changing the color gamut or improving the optical characteristics; and the like.

[Polarizing element]
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 produced 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.
Further, the polarizing element is not limited to an anisotropic dye film, but is an overcoat layer having functions such as improving polarization performance and mechanical strength; an adhesive layer or an antireflection layer; an alignment film; as a retardation film. It may be used in combination with a layer having optical functions such as a function as a brightness improving film, a function as a reflection or antireflection film, a function as a transflective reflective film, and a function as a diffusion film; .. Specifically, the above-mentioned layers having various functions may be laminated and formed by coating, bonding, or the like, and used as a laminated body.
These layers can be appropriately provided according to the manufacturing process, characteristics, and functions, and the position and order of lamination thereof are not particularly limited. For example, the position where each layer is formed may be formed on the anisotropic dye film or may be formed on the opposite surface of the substrate on which the anisotropic dye film is provided. Further, the order in which each layer is formed may be before or after the anisotropic dye film is formed.

The layer having these optical functions can be formed by the following method.
The layer having a function as a retardation film can be formed by applying or bonding the retardation film to other layers constituting the polarizing element. The retardation film is, for example, subjected to the stretching treatment described in Japanese Patent Application Laid-Open No. 2-59703, Japanese Patent Application Laid-Open No. 4-230704, etc., or described in Japanese Patent Application Laid-Open No. 7-230007. It can be formed by subjecting it to treatment.

The layer having a function as the brightness improving film can be formed by applying or bonding the brightness improving film to other layers constituting the polarizing element. The brightness-improving film has, for example, formed micropores by a method as described in Japanese Patent Application Laid-Open No. 2002-1690.25 and Japanese Patent Application Laid-Open No. 2003-29030, or has a center wavelength of selective reflection. It can be formed by superimposing two or more different cholesteric liquid crystal layers.

The layer having a function as a reflective film or a transflective reflective film is formed by, for example, applying or bonding a metal thin film obtained by vapor deposition or sputtering to another layer constituting the polarizing element. Can be done.
The layer having a function as a diffusion film can be formed, for example, by coating another layer constituting the polarizing element with a resin solution containing fine particles.

The layer having a function as a retardation film or an optical compensation film is composed of a liquid crystal compound such as a discotic liquid crystal compound, a nematic liquid crystal compound, a smectic liquid crystal compound, or a cholesteric liquid crystal compound, and another layer constituting the polarizing element. It can be formed by applying it to and orienting it. At that time, an alignment film may be provided on the substrate, and a retardation film or an optical compensation film may be formed on the surface of the alignment film.

When the anisotropic dye film of the present invention is used as an anisotropic dye film or the like for various display elements such as LCDs and OLEDs, the present invention is directly applied to the surface of the electrode substrate or the like constituting these display elements. An anisotropic dye film may be formed, or a substrate on which the anisotropic dye film of the present invention is formed may be used as a constituent member of these display elements.

The present invention will be described in more detail with reference to Examples, but the present invention is not limited to the following Examples as long as the gist of the present invention is not exceeded.
In the following description, "part" means "part by weight".

[Method for identifying liquid crystal phase]
The liquid crystallinity of the obtained anisotropic dye film forming composition includes differential scanning calorimetry (Seiko Instruments Co., Ltd. "DSC220CU"), X-ray structure analysis (Rigaku Co., Ltd. "NANO-Viewer"), and hot stage (Co., Ltd.). Observe by either method of a polarizing microscope (Nikon Instec Co., Ltd. "ECLIPSE LV100N POL") attached to Toyo Technica "HCS302-LN190" or a combination of multiple methods, and "LCD Handbook" (Maruzen). The liquid crystal was identified according to the method described on pages 9 to 50, 117 to 176, etc. of Co., Ltd. (issued on October 30, 2000).

[How to check haze]
To confirm the haze of the obtained liquid crystal film and the anisotropic dye film, place the sample on A4 paper equipped with a backlight and printed characters, and visually confirm the superiority or inferiority of the haze by three or more people. , Either or both of the methods of measuring with a haze meter (Nippon Denshoku Industries Co., Ltd. "NDH5000SP") were used.

[Measurement of transmittance and two-color ratio for polarized light in the absorption axis / polarization axis direction of the anisotropic dye film]
The dichroism of the obtained anisotropic dye film can be confirmed by holding the absorption axis of the polarizing plate at 0 ° and 90 ° with respect to the absorption axis of the anisotropic dye film. At that time, if the light and darkness is 0 ° and 90 °, it can be judged that there is dichroism.
The transmittance of the obtained anisotropic dye film with respect to polarization in the absorption axis / polarization axis direction was determined by using a spectrophotometer equipped with a Gran Thomson polarizer (manufactured by Otsuka Electronics Co., Ltd., product name "RETS-100"). It was measured.
The measurement light of linearly polarized light is incident on the anisotropic dye film, and the transmittance of the anisotropic dye film with respect to the polarization in the absorption axis direction and the transmittance of the anisotropic dye film with respect to the polarization in the polarization axis direction are measured. The two-color ratio (D) was calculated as described above.
D = Az / Ay
(During the ceremony,
Ay = -log (Ty);
Az = -log (Tz);
Tz is the transmittance of the anisotropic dye film for polarization in the absorption axis direction;
Ty is the transmittance of the anisotropic dye film with respect to polarized light in the polarization axis direction. )

Specifically, a sandwich cell (cell gap: 8.0 μm, 10.0 μm, 12.0 μm, film formation) in which a polyimide alignment film (LX1400, manufactured by Hitachi Chemical DuPont Microsystems) is formed on glass as a base material. An anisotropic dye film is obtained by injecting the composition for an anisotropic dye film into an isotropic phase and cooling the finished polyimide (which has been previously subjected to rubbing treatment with a cloth), and dichroic at each temperature. The presence or absence of sex was confirmed.

Hereinafter, the present invention will be described with reference to specific examples.

[Synthesis of liquid crystal compounds]
<Liquid crystal compound (I-1)>
The liquid crystal compound (I-1) was synthesized according to the synthesis method described below.

Synthesis of (A-1-a):

A solution of p-iodophenol (285 g, 1.3 mol), potassium carbonate (358 g, 2.6 mol) and 11-bromo-1-undecanol (325 g, 1.3 mol) in N, N-dimethylformamide (800 mL) under nitrogen. , Stirred at 80 ° C. for 2 hours and allowed to cool to room temperature. After adding to 1 L of water, the precipitate was separated by filtration and washed with water and hexane. The obtained crude product is dissolved in methylene chloride, washed with water and saturated brine, dried over sodium sulfate, filtered, and concentrated to add 85% of 430 g of a white solid (A-1-a). Obtained in yield.

Synthesis of (A-1-b):

In a solution of A-1-a (430 g, 1.1 mol), DBU (369 mL, 2.4 mol) in dimethyl sulfoxide DMSO (1.5 L), Pd (PPh3) 4 (63 g, 55 mmol) and propioil acid (85 g, 1.2 mol) of DMSO solution (500 mL) was added, and the mixture was stirred at 20 ° C. for 18 hours. 1 L of ethyl acetate was added to the obtained reaction solution, back extraction was performed with an aqueous sodium hydrogen carbonate solution, and the aqueous layer was washed with ethyl acetate. A 2M-HCl aqueous solution was added to the obtained aqueous layer to set pH = 1, and the precipitate was filtered and then washed with water and hexane to yield 81% of A-1-b (300 g, 0.9 mol). Obtained at a rate.

Synthesis of (A-1-c):

A-1-b (285 g, 857 mol), N, N-dimethylaniline (208 g, 1.7 mol), BHT (1.9 g, 8.5 mmol) in THF (2.5 L) under nitrogen, while cooling with ice. Acrylic acid chloride (108 g, 1.2 mol) was added, and the mixture was stirred at 25 ° C. for 4 hours. After concentration, the mixture was added to ice-cooled hydrochloric acid and extracted with methylene chloride. After adding 20 g of activated carbon and stirring, Celite filtration was performed. Further, activated clay was added, and the mixture was stirred and then filtered through Celite to obtain A-1-c (223 g, 577 mmol) in a yield of 67%.

Synthesis of (A-2-a):

A-2-a (11.2 g, 44.7 mmol) was synthesized in a yield of 85% with reference to the literature of J. Mater. Chem. C, 2017, 5, 9345-9358.

Synthesis of (A-2-b):

A-2-a (11.2 g, 44.7 mmol) in methanol: acetic acid (10: 1) 160 mL solution was charged with 5% Rh / Al2O3 (5.2 g, 2.5 mmol), hydrogen-substituted, and then 2 The pressure was increased to 5.5 MPa, and the mixture was stirred at 100 ° C. for 24 hours. After nitrogen substitution, Celite was filtered and concentrated. Ethyl acetate was added to the obtained crude product to dissolve it, activated carbon was added, and the mixture was stirred and then filtered through Celite to obtain A-2-b (10.6 g, 41.3 mmol) in a yield of 92%. It was.

Synthesis of (A-2-c):

28% NaOMe / MeOH (67 g, 347 mmol) was added dropwise to a solution of A-2-b (29.7 g, 115.8 mmol) in methanol (300 mL), and the mixture was heated and stirred for 72 hours. After cooling, the mixture was added to 1NHCl (300 mL), extracted with methylene chloride, the organic layer was washed with water and saturated brine, magnesium sulfate was added, and the mixture was dried and concentrated under reduced pressure. 250 mL of water and KOH (17.7 g, 315.9 mmol) were added to the obtained crude product, and the mixture was refluxed for 4 hours. After cooling to room temperature, add 2N aqueous HCl solution to pH = 1, extract with ethyl acetate, wash the organic layer with water and saturated brine, add magnesium sulfate, dry, and concentrate by filtration. As a result, a crude product was obtained. The obtained crude product was purified by silica gel chromatography (developing solution: hexane: ethyl acetate = 8: 1) to obtain A-2-c (8.9 g, 39 mmol) as a white solid in a yield of 33%. Obtained.

Synthesis of (A-2-d):

Triethylamine (0.67 mL, 4.8 mmol), dimethylaminopyridine (0.03 g, 0.03 g,) in a methylene chloride solution (10 mL) of A-2-c (1 g, 4.4 mmol) and Deoxyarbutin (0.93 g, 4.8 mmol). 0.24 mmol) and EDC / HCl (0.92 g, 4.8 mmol) were added, and the mixture was stirred at 20 ° C. for 6 hours. The obtained solution was added to water, extracted with methylene chloride, washed with water and saturated brine, dried over sodium sulfate, and concentrated by filtration to obtain a crude product. The obtained crude product was purified by silica gel chromatography (hexane: ethyl acetate = 3: 1) to obtain a white solid of A-2-d (1.73 g) in a yield of 97%.

Synthesis of (A-2-e):

PPTS (515 mg, 0.2 mmol) of pyridinium paratoluenesulfonic acid was added to an ethanol solution (85 mL) of A-2-d (9.0 g, 22.2 mmol), and the mixture was stirred at 60 ° C. for 2 hours. After concentration, 110 mL of 0.1 M hydrochloric acid was added to the residue, and extraction was performed with ethyl acetate. The obtained organic layer was washed with a saturated aqueous solution of NaHCO3 and a saturated brine, and then sodium sulfate was added and dried. The insoluble matter was filtered and then concentrated to obtain a pale yellow solid of the target product A-2-e (7.1 g) in a yield of 99%.

Synthesis of liquid crystal compound (I-1):

EDC (6 mL) in a methylene chloride solution (6 mL) of A-1-c (500 mg, 1.29 mmol), A-2-e (455 mg, 1.42 mmol) and dimethylaminopyridine (32 mg, 0.26 mmol) under a nitrogen atmosphere. 0.25 mL (1.42 mmol) was added, and the mixture was stirred at 20 ° C. for 6 hours. 20 mL of water was added to the obtained reaction solution, and extraction was performed with methylene chloride. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated by filtration to obtain a crude product (1.4 g). The obtained crude product was purified by column chromatography (developing solution: hexane / chloroform = 1: 5) to obtain a white solid of liquid crystal compound (I-1) (474 mg) in a yield of 46%.

The chemical structural formulas of the liquid crystal compounds synthesized above and the dyes used in the following Examples or Comparative Examples are shown below.

(I-1)

(II-2)

[Example 1]
To 79.73 parts of chloroform, 20.00 parts of the liquid crystal compound (I-1) and 0.27 parts of the azo dye of the formula (II-1) are added, and the mixture is stirred and compatible, and then the solvent is removed. As a result, the composition 1 for forming an anisotropic dye film was obtained.
Using the obtained anisotropic dye film forming composition 1, an anisotropic dye film 1 was prepared by the above-mentioned method, and the dichroism of the anisotropic dye film 1 was confirmed. It was confirmed that when the obtained anisotropic dye film 1 was held over a commercially available polarizing plate and rotated, it became bright and dark, and exhibited good performance that could be used as a polarizing film.

[Example 2]
69.85 parts of cyclopentanone, 28.57 parts of liquid crystal compound (I-1), 1.29 parts of azo dye of formula (II-1), IRGACURE® 369 (BASF product). 0.29 parts are added, and after heating and stirring at 80 ° C., the composition 2 for an anisotropic dye film is obtained by filtering using a syringe equipped with a syringe filter (PTFE13045, caliber 0.45 μm, manufactured by Membrane Solutions). Obtained.
The composition 2 for an anisotropic dye film is formed on a substrate on which a polyimide alignment film (LX1400, manufactured by Hitachi Kasei DuPont Microsystems, manufactured by the rubbing method) is formed on glass by a spin coating method. After heating and drying to the isotropic phase, the mixture was cooled to the liquid crystal phase ^{and polymerized at an exposure amount of 500 mj / cm 2} (365 nm standard) to obtain an anisotropic dye film 2. When the obtained anisotropic dye film 2 was confirmed, it was confirmed that it was a good coating film with less haze and was useful when used as an optical material.

Claims (13)

An anisotropic dye film forming composition containing a dye and a liquid crystal compound.
A composition for forming an anisotropic dye film, wherein the liquid crystal compound contains a liquid crystal compound represented by the formula (1).
R1-A1-Y1-A2-Y2-A3-R2 ... (1)
In equation (1),
R1 and R2 represent a chain organic group having a polymerizable group on one side and a non-polymerizable chain organic group on the other side;
The sum of the chain lengths of R1 and R2 is 7 or more;
A1 and A3 independently represent a partial structure represented by the formula (2), a divalent organic group, or a single bond;
A2 represents a partial structure or a divalent organic group represented by the formula (2);
-Y1- and -Y2- are independently single-bonded, -C (= O) O-, -OC (= O)-, -C (= S) O-, -OC (= S)-, respectively. -C (= O) S-, -SC (= O)-, -CH ₂ CH _2- , -CH = CH-, -C (= O) NH-, -NHC (= O)-, -CH ₂ Represents O-, -OCH _2- , -CH ₂ S-, or -SCH _2- ;
One of A1 and A3 is a partial structure or a divalent organic group represented by the formula (2);
At least one of A1, A2, and A3 is a partial structure represented by the formula (2).
-Cy-X2-C≡C-X-... (2)
In equation (2),
Cy represents a hydrocarbon ring group or a heterocyclic group;
-X- is -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 Represents S- or -SCH _2- ;
-X2- is 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- , Represents −CH ₂ S− or −SCH _2−. The difference according to claim 1, wherein −X− is −C (= O) O−, −OC (= O) −, −CH ₂ CH ₂ −, −CH ₂ O−, or −OCH _2−. Composition for forming an anisotropic pigment film. The composition for forming an anisotropic dye film according to claim 1 or 2, wherein Cy in the formula (2) is a hydrocarbon ring group and -X2- is a single bond. One of A1, A2, and A3 is a partial structure represented by the above formula (2), and the other two are independently divalent organic groups.
In the formula (2), Cy is a hydrocarbon ring group, -X2- is a single bond, and
The composition for forming an anisotropic dye film according to any one of claims 1 to 3, wherein the divalent organic group is a hydrocarbon ring group. The composition for forming an anisotropic dye film according to any one of claims 1 to 4, wherein Cy in the formula (2) is a 1,4-phenylene group or a cyclohexane-1,4-diyl group. .. The composition for forming an anisotropic dye film according to any one of claims 1 to 5, wherein Cy in the formula (2) is a 1,4-phenylene group. The polymerizable organic group is a − (CH ₂ ) _n − polymerizable group, −O − (CH ₂ ) _n-1 -polymerizable group, and n is an integer of 3 or more. The composition for forming an anisotropic dye film according to any one of 1 to 6. The anisotropic dye film formation according to any one of claims 1 to 7, wherein the non-polymerizable chain organic group is a linear or branched alkyl group having a chain length of 6 or more. Composition for. -Y1- and -Y2- are independently single-bonded, -C (= O) O-, -OC (= O)-, -CH ₂ CH _2- , -CH ₂ O- or -OCH _2- And
Any of claims 1 to 8, wherein −X− is −C (= O) O−, −OC (= O) −, −CH ₂ CH ₂ −, −CH ₂ O− or −OCH _{2 −.} The composition for forming an anisotropic dye film according to item 1. The composition for forming an anisotropic dye film according to any one of claims 1 to 9, wherein one of A1 and A3 is a cyclohexane-1,4-diyl group. The anisotropy according to any one of claims 1 to 10, wherein one of A1 and A3 is a partial structure represented by the above formula (2) and the other is a cyclohexane-1,4-diyl group. Composition for forming a sex pigment film. An anisotropic dye film formed by using the composition for forming an anisotropic dye film according to any one of claims 1 to 11. An optical element comprising the anisotropic dye film according to claim 12.