KR101245628B1 - Epoxy compound for liquid crystal alignment agent, liquid crystal alignment agent, liquid crystal alignment film - Google Patents

Abstract

An epoxy compound for a liquid crystal photoalignment agent, a liquid crystal photoalignment agent, and a liquid crystal photoalignment film are provided, and the epoxy compound is a compound represented by the following Chemical Formula 1.

[Formula 1] 　

In Formula 1, each substituent is as defined in the specification.

Epoxy compound according to an embodiment of the present invention can be prepared by a simple manufacturing process, it is economical, can provide a liquid crystal photo-alignment agent and an optical alignment layer excellent in printability to the substrate, and excellent in terms of reliability and electro-optic properties. have.

Epoxy, liquid crystal photoalignment film, liquid crystal photoalignment agent, epoxy, polyamic acid, polyimide, photo alignment agent, afterimage

Description

Epoxy compound for liquid crystal photo-alignment agent, liquid crystal photo-alignment agent, and liquid crystal photo-alignment film {EPOXY COMPOUND FOR LIQUID CRYSTAL ALIGNMENT AGENT, LIQUID CRYSTAL ALIGNMENT AGENT, LIQUID CRYSTAL ALIGNMENT FILM}

The present invention relates to an epoxy compound for a liquid crystal photoalignment agent, a liquid crystal photoalignment agent, a photocatalyst, and a liquid crystal photoalignment film.

Liquid crystal display (LCD) uses a liquid crystal alignment film. As the liquid crystal alignment film, a polymer material is mainly used. The liquid crystal alignment layer acts as a director in the array of liquid crystal molecules, thereby allowing the liquid crystal to move in an electric field to form an appropriate direction. In general, in order to obtain uniform brightness and high contrast ratio, it is essential to orient the liquid crystal uniformly.

Conventionally, the rubbing method which apply | coated a polymer film like polyimide to the board | substrates, such as glass, and rubbed the surface in a fixed direction with fibers, such as a nylon and polyester, was the conventional method of orienting a liquid crystal. However, the rubbing method may generate fine dust or electrostatic discharge (ESD) when the fiber and the polymer film are rubbed, which may cause serious problems in manufacturing the liquid crystal panel.

In order to solve the problem of the rubbing method, in recent years, an optical alignment method of inducing anisotropy (anisotropy, anisotropy) to a polymer film by light irradiation rather than friction and arranging liquid crystals by using a wire has been studied.

As a material that can be used in the photo-alignment method, a study has been made on the diamine containing an optical functional group such as azobenzene, cumarin, chalcone and cinnamate. To prepare a diamine having such a photofunctional group, a dinitro-based compound having excellent stability should be used, but in the process of preparing a diamine using a dinitro-based compound, a reaction such as photocrosslinking may occur by polarized light irradiation. There is a fear that the double bond is broken, there is a problem that is difficult to apply to the photo-alignment agent. In addition, there is a problem in that the process for producing a diamine containing a photofunctional group is too complicated and economical.

One embodiment of the present invention is to provide an epoxy compound for a liquid crystal photo-alignment agent that can be prepared by a simple process, can provide a photo-alignment agent with excellent brightness and the like.

Another embodiment of the present invention is to provide a liquid crystal photo-alignment agent containing the epoxy compound, and excellent in characteristics such as brightness.

Another embodiment of the present invention is to provide a liquid crystal photoalignment film having excellent characteristics such as luminance by using the liquid crystal photoalignment agent.

The technical problems to be achieved by the present invention are not limited to the above-mentioned technical problems, and other technical problems not mentioned will be clearly understood by the average technician from the following description.

According to one embodiment of the present invention, an epoxy compound for a liquid crystal photoalignment agent represented by Chemical Formula 1 is provided.

[Formula 1]

(In the formula 1,

R ₁ and R ₂ are each independently a hydrogen atom; Or a substituted or unsubstituted alkyl group,

R ₃ , R ₄ and R ₅ are each independently a hydrogen atom; A halogen group; Or a substituted or unsubstituted alkyl group,

n is 1 to 20.)

According to another embodiment of the present invention, the epoxy compound represented by Formula 1; And a polymer which is a polyamic acid, a polyimide polymer, or a mixture thereof.

According to another embodiment of the present invention provides a liquid crystal photo-alignment film prepared by applying the liquid crystal photo-alignment agent to a substrate.

Other specific details of embodiments of the present invention are included in the following detailed description.

Liquid crystal photo-alignment agent according to an embodiment of the present invention can produce a liquid crystal photo-alignment film excellent in printability to the substrate, and excellent in reliability and electro-optic properties.

Hereinafter, embodiments of the present invention will be described in detail. However, this is presented as an example, whereby the present invention is not limited and the present invention is defined only by the scope of the claims to be described later.

Unless otherwise specified herein, "alkyl group" means an alkyl group having 1 to 30 carbon atoms, "cycloalkyl group" means a cycloalkyl group having 3 to 30 carbon atoms, and an alkylene group having 1 to 6 carbon atoms, "alkylene group", "Cycloalkylene group" means a C3-C30 cycloalkylene group, "heterocycloalkylene group" means a C2-C30 heterocycloalkylene group, "aryl group" means an aryl group of C6-C30, and "heteroaryl" Group "means a C2-C30 heteroaryl group," arylene "group refers to a C2-C20 arylene group," heteroarylene group "means a C2-C30 heteroarylene group," alkylaryl group " An alkylaryl group having C7-C30 carbon atoms, and a halogen atom or a halogen group means F, Cl, Br, or I.

Substituted alkyl group, substituted alkylene group, substituted cycloalkylene group, substituted heterocycloalkylene group, substituted aryl group, substituted arylene group, substituted heteroaryl group, substituted heteroarylene group, substituted pyriin The midinyl group, substituted pyridinyl group, substituted thiophenyl group, substituted furanyl group, substituted naphthyl group, and substituted phenyl group are each independently a halogen group, an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, Alkyl group, alkylene group, cycloalkylene group, heterocycloalkyl substituted with a substituent selected from the group consisting of an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, and a combination thereof An ylene group, an aryl group, an arylene group, a heteroaryl group, a heteroarylene group, a pyrimidinyl group, a pyridinyl group, a thiophenyl group, a furanyl group, a naphthyl group, and a phenyl group.

In the present specification, the heterocycloalkylene group, the heteroaryl group, and the heteroarylene group each independently contain 1 to 3 heteroatoms of N, O, S, Si, or P in one ring, and the rest are carbons. It means a cycloalkylene group, an aryl group, and a arylene group.

Epoxy compound for liquid crystal photo-alignment agent according to an embodiment of the present invention may be represented by the formula (1).

[Formula 1]

In Formula 1,

R ₁ and R ₂ are each independently a hydrogen atom; Or a substituted or unsubstituted alkyl group,

R ₃ , R ₄ and R ₅ are each independently a hydrogen atom; A halogen group; Or a substituted or unsubstituted alkyl group,

n is 1 to 20.

In one embodiment of the present invention, R ₁ and R ₂ are each independently a hydrogen atom, R ₃ , R ₄ and R ₅ are each independently a halogen atom, n may be 2.

Specific examples of the epoxy compound may include at least one of the compounds represented by the following Chemical Formulas 2 to 3.

[Formula 2]

(3)

The epoxy compound may be prepared by a simple manufacturing process, and when the epoxy compound is used in the liquid crystal photoalignment agent, it reacts with the COOH of the polyamic acid to reduce the COOH remaining in the liquid crystal photoalignment agent, thereby preventing afterimages. It is possible to obtain an effect such as luminance improvement.

The epoxy compound may be prepared by the following process .

The compound represented by Chemical Formula 1-A and the compound represented by Chemical Formula 1-B are reacted in an organic solvent.

[Chemical Formula 1-A]

(In Formula 1-A, R ₁ , R ₂ , R ₃ , R ₄ and R ₅ are as defined above, and R ₆ is a hydrogen atom.)

[Formula 1-B]

(In Formula 1-B, R ₇ is a hydrogen atom.)

As the organic solvent, methylene chloride, tetrahydrofuran, diethyl ether, ethylene chloride or one or more thereof may be mixed and used.

The reaction molar ratio of the compound of Formula 1-A and the compound of Formula 1-B is preferably 1: 1.2 to 1: 2.

In addition, the reaction may be carried out in the presence of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, 3-dimethylamino propylamine,, or a nitrogen-containing compound which may be used by mixing one or more thereof. .

Once the reaction is complete, a general purification procedure may be further carried out, washing the product with water, filtration and drying.

Liquid crystal photo-alignment agent according to another embodiment of the present invention is an epoxy compound represented by the formula (1); And polymers that are polyamic acids, polyimide polymers, or mixtures thereof.

Hereinafter, each component will be described in detail.

(A) epoxy compound

The epoxy compound may be represented by Chemical Formula 1. The liquid crystal photoalignment agent used as an additive which mixes an epoxy compound with a polymer, such as a polyamic acid, a polyimide polymer, or a mixture thereof, is excellent in brightness, and the effect which prevents an afterimage can be obtained.

The content of the epoxy compound according to one embodiment of the present invention is 0.01 to 60 parts by weight, and 0.01 to 40 parts by weight based on 100 parts by weight of the solid content (in the liquid crystal aligning agent, which is an epoxy compound and a polymer). When the content of the epoxy compound is included in the above range, the photopolymerization reaction can occur appropriately without lowering the printability and flatness when applied to the substrate, it can be usefully used as a photo-alignment agent.

Specific examples of the epoxy compound may include at least one of the compounds represented by the following Chemical Formulas 2 to 3.

[Formula 2]

(3)

(B) polymer

The polymer may be a polyamic acid, a polyimide polymer or a mixture thereof. In addition, when a mixture of the polyamic acid and the polyimide polymer is used, it can be used in a ratio of 1 to 99% by weight and 99 to 1% by weight.

(B-1) polyamic acid

The polyamic acid used for the liquid crystal photoalignment agent can be used as long as it is a polyamic acid synthesized from an acid dianhydride and diamine.

As said acid dianhydride, aliphatic cyclic acid dianhydride, aromatic acid dianhydride, or these can be used in mixture of 1 or more types. As the diamine, aromatic diamines and functional diamines may be used alone, or aromatic diamines and functional diamines may be mixed and used. In the case where a mixture of aromatic diamine and functional diamine is used, the liquid crystal alignment film may easily adjust the pretilt angle of the liquid crystal molecules and may have more excellent orientation.

The method of preparing the polyamic acid by copolymerizing the acid dianhydride and the diamine may be applied without being limited to a method known to be capable of copolymerizing the conventional polyamic acid.

Examples of the specific polyamic acid according to an embodiment of the present invention include the following formula (5).

[Chemical Formula 5]

In Formula 5,

R ₃₁ is a tetravalent organic group derived from an aliphatic cyclic dianhydride or an aromatic acid dianhydride,

R ₃₂ is a divalent organic group derived from diamine.

(B-1-1) Acid Anhydride

(B-1-1-1) Aliphatic Cyclic Acid Anhydride

The aliphatic cyclic acid dianhydrides include 1,2,3,4-cyclobutanetetracarboxylic dianhydride (CBDA), 5- (2,5-dioxotetrahydrofuryl) -3-methylcyclohexene-1,2 -Dicarboxylic acid anhydride (DOCDA), bicyclooctene-2,3,5,6-tetracarboxylic dianhydride (BODA), 1,2,3,4-cyclopentanetetracarboxylic dianhydride (CPDA), 1,2,4,5-cyclohexanetetracarboxylic dianhydride (CHDA), 1,2,4-tricarboxy-3-methylcarboxy cyclopentane dianhydride, 1,2,3,4-tetracarboxy cyclopentane Anhydride, 4,10-dioxa-tricyclo [6.3.1.02,7] dodecane-3,5,9,11-tetraone or a mixture of one or more thereof may be used, but is not limited thereto.

The tetravalent organic group derived from the aliphatic cyclic acid dianhydride may have a structure of at least one of the compounds represented by the following Chemical Formulas 7 to 11.

[Formula 7]

 [Formula 8]

[Chemical Formula 9]

　　

　　

[Formula 10]

　　　　　

　　　　

[Formula 11]

(In Chemical Formulas 7 to 11,

R ₄₀ is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, n ₁₀ is an integer of 0 to 3,

R ₄₁ to R ₄₇ are each independently a hydrogen atom; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.)

(B-1-1-2) aromatic acid dianhydride

The aromatic acid dianhydrides include pyromellitic dianhydride (PMDA), nonphthalic dianhydride (BPDA), oxydiphthalic dianhydride (ODPA), benzophenone tetracarboxylic dianhydride (BTDA), and hexafluoroisopropylidene diphthalic acid. Anhydride (6-FDA), or may be used by mixing one or more thereof, but is not limited thereto.

The tetravalent organic group derived from the aromatic acid dianhydride may have a structure of at least one of a compound represented by Formula 12 or a compound represented by Formula 13.

[Chemical Formula 12]

[Chemical Formula 13]

(In Chemical Formula 12 and Chemical Formula 13)

R ₅₁ , and R ₅₂ are each independently a hydrogen atom; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms,

R ₅₄ and R ₅₅ are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms,

n ₅₄ , and n ₅₅ are each independently an integer of 0 to 3,

R ₅₃ is O; CO; Substituted or unsubstituted alkylene group (for example: -C (CF ₃ ) _2- ); A substituted or unsubstituted cycloalkylene group; Or a substituted or unsubstituted heterocycloalkylene group,

n ₅₃ is an integer of 0 or 1)

(B-1-2) diamine

(B-1-2-1) aromatic diamine

Examples of the aromatic diamine include paraphenylenediamine (p-PDA), 4,4-methylenedianiline (MDA), # 2,2'-dimethyl benzidine (DMBZ), 3,3'-dimethyl benzidine, and 4,4-jade. Cydianillin (ODA), metabisaminophenoxydiphenylsulfone (m-BAPS), parabisaminophenoxydiphenylsulfone (p-BAPS), 2,2-bisaminophenoxyphenylpropane (BAPP), 2,2- Bisaminophenoxyphenylhexafluoropropane (HF-BAPP), 1,4-diamino-2-methoxybenzene, or a mixture of one or more thereof may be used, but is not limited thereto.

The divalent organic group derived from the aromatic diamine may have a structure of at least one of the compounds represented by the following Chemical Formulas 14 to 16.

[Formula 14]

[Formula 15]

[Chemical Formula 16]

(In Chemical Formulas 14 to 16,

R ₆₁ , R ₆₃ , R ₆₄ , and R ₆₇ to R ₆₉ each independently represent a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; Or the alkyl group, aryl group, or heteroaryl group further comprising one of -O-, -COO-, -CONH- or -OCO-,

R ₆₂ , R ₆₅ , and R ₆₆ are each independently C (R ′) (R ″), such as —O—, —SO ₂ —, or —C (CF ₃ ) ₂ —, wherein R ′, And R '' are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms,

N ₆₁ , n ₆₃ , n ₆₄ , and n ₆₇ to n ₆₉ are each independently an integer of 0 to 4,

N ₆₂ , n ₆₅ , and n ₆₆ are each independently an integer of 0 or 1)

(B-1-2-2) Functional Diamine

As the functional diamine, compounds represented by the following Chemical Formulas 17 to 19, or one or more thereof may be mixed and used. When functional diamines are used in combination with aromatic diamines, some of the polyamic acids produced will contain functional groups derived from aromatic diamines, and some will contain divalent organic groups derived from functional diamines.

[Chemical Formula 17]

(In the above formula (17)

R ₇₁ is a hydrogen atom; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms,

R ₇₂ is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted hetero aryl group having 2 to 30 carbon atoms, and n ₇₂ is an integer of 0 to 3)

[Chemical Formula 18]

(In the above formula (18)

R ₇₃ , R ₇₅ , and R ₇₆ each independently represent a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms,

R ₇₄ is —O—; -COO-; -CONH-; -OCO-; Or a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms,

R ₇₇ is a hydrogen atom; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; Or the alkyl group, aryl group, or heteroaryl group further comprising at least one of -O-, -COO-, -CONH-, or -OCO-,

n ₇₃ is an integer from 0 to 3,

n ₇₅ , and n ₇₆ are each independently an integer of 0 to 4,

n ₇₄ is an integer of 0 or 1)

[Formula 19]

(In Chemical Formula 19,

R ₈₁ and R ₈₃ each independently represent a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms,

R ₈₂ is a hydrogen atom; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms,

R ₇₈ , and R ₇₉ are each independently -O-, or -COO-,

R ₈₀ is —O—, —COO—, —CONH—, or —OCO—,

n ₈₁ , and n ₈₃ are each independently an integer of 0 to 4,

n ₇₈ to n ₈₀ are each independently an integer of 0 or 1)

(B-2) polyimide polymer

The polyimide polymer may be any of polyimide polymer or polyimide photopolymer used in liquid crystal photopolymer .

The polyimide polymer may be prepared by imidizing the polyamic acid represented by Chemical Formula 1, or may be synthesized from one or more kinds of photodiamine and acid dianhydride. Since a method of preparing a polyimide polymer by imidating a polyamic acid and a method of preparing a polyimide polymer from photodiamine and an acid dianhydride is well known in the art, detailed description thereof will be omitted.

Specific examples of the polyimide polymer according to one embodiment of the present invention include a compound represented by the following formula (6).

[Formula 6]

In Formula 6,

R ₃₃ is a tetravalent organic group derived from an aliphatic cyclic acid dianhydride or an aromatic acid dianhydride,

R ₃₄ is a divalent organic group derived from an aromatic diamine or a divalent organic group derived from a cumarin photodiamine, a chalcone photodiamine, or a cinnamate photodiamine.

(B-2-1) Acid dianhydride

The acid dianhydride used to prepare the polyimide polymer may be used an aliphatic cyclic acid dianhydride, an aromatic acid dianhydride, or a mixture thereof, as described in the polyamic acid.

(B-2-2) photodiamine

The photodiamine used to prepare the polyimide polymer may be used with cinnamate photodiamine, chalcone photodiamine, coumarin photodiamine, or a mixture of one or more thereof.

In the present invention, the cinnamate photodiamine may be a compound represented by the following Formula 20, a compound represented by the following Formula 21, or a mixture of one or more thereof, and the chalcone photodiamine is represented by the following Formula 22: The compound to be used can be used, and the compound represented by the following formula (23) can be used as the coumarin-based photodiamine.

[Chemical Formula 20]

(In the above formula (20)

R ₉₁ is a hydrogen atom; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R ₉₂ is a substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, n ₇₂ is an integer of 0 to 3)

[Chemical Formula 21]

(In the formula (21)

R ₉₇ is an aromatic diamine group, a diamine group including a substituted or unsubstituted linear or branched alkylene group having 2 to 24 carbon atoms, or a combination thereof,

In R ₉₇ , the substituted alkylene group may include an alkylene group in which a hydrogen atom is substituted with a halogen atom or a cyano group; At least one non-adjacent CH ₂ group of the alkylene group is substituted or unsubstituted arylene group, substituted or unsubstituted heteroarylene group, substituted or unsubstituted cycloalkylene group, substituted or unsubstituted heterocycloalkylene group, -O -, -CO-, -CO-O-, -O-CO-, -Si (CH ₃ ) ₂ -O-Si (CH ₃ ) _2- , -NR'-, -NR'-CO-, -CO —NR′—, —NR′—CO—O—, —O—CO—NR′—, —CH═CH—, —C≡C—, or —O—CO—O—, where R ′ is hydrogen. Or an alkylene group substituted with a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; Or a combination of these alkylene groups,

R ₉₄ is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, n ₇₄ is an integer of 0 to 4,

R ₉₅ and R ₉₆ each independently represent a hydrogen atom; A halogen atom; Cyano; Or a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms,

The alkyl group substituted in R ₉₅ and R ₉₆ is an alkyl group in which a hydrogen atom is substituted with a hetero atom or a cyano group; An alkyl group wherein at least one non-adjacent CH ₂ group of the alkyl group is substituted with —O—, —CO—O—, —O—CO—, or —CH═CH—; Or a combination of these alkyl groups,

R ₉₃ is a substituted or unsubstituted alkyl group; Substituted or unsubstituted alkylaryl groups; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted pyrimidinyl group; Substituted or unsubstituted pyridinyl group; Substituted or unsubstituted thiophenyl group; Substituted or unsubstituted furanyl group; Substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted phenyl group,

The substituted alkyl group in R ₉₃ is an alkyl group in which a hydrogen atom is substituted with halogen or cyano group; An alkyl group wherein at least one non-adjacent CH ₂ group of the alkyl group is substituted with —O—, —CO—O—, —O—CO—, or —CH═CH—; Or a combination of these alkyl groups,

The substituted alkylaryl group in R ₉₃ is an alkylaryl in which one or more non-adjacent CH ₂ groups of the alkylaryl group are substituted with -O-, -CO-O-, -O-CO-, or -CH = CH-. Ki)

[Formula 22]

(In Chemical Formula 22,

R ₁₀₁ is an aromatic diamine group; A diamine group substituted with a substituted or unsubstituted linear or branched alkylene group having 2 to 24 carbon atoms, or a combination thereof,

The substituted alkylene group in R ₁₀₁ is an alkylene group in which a hydrogen atom is substituted with a halogen atom or a cyano group; At least one non-adjacent CH ₂ group of the alkylene group is substituted or unsubstituted arylene group, substituted or unsubstituted heteroarylene group, substituted or unsubstituted cycloalkylene group, substituted or unsubstituted heterocycloalkylene group, -O -, -CO-, -CO-O-, -O-CO-, -Si (CH ₃ ) ₂ -O-Si (CH ₃ ) _2- , -NR'-, -NR'-CO-, -CO —NR′—, —NR′—CO—O—, —O—CO—NR′—, —CH═CH—, —C≡C—, or —O—CO—O—, where R ′ is hydrogen. An alkylene group substituted with an atom or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; Or a combination of these alkylene groups,

R ₁₀₂ and R ₁₀₅ each independently represent a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, n ₁₀₂ and n ₁₀₅ are each independently an integer of 0 to 4,

R ₁₀₃ and R ₁₀₄ are each independently a hydrogen atom; A halogen atom; Cyano; Or a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms,

The substituted alkyl group in R ₁₀₃ and R ₁₀₄ is an alkyl group in which a hydrogen atom is substituted with a halogen atom or a cyano group; An alkyl group wherein at least one non-adjacent CH ₂ group of the alkyl group is substituted with —O—, —CO—O—, —O—CO—, or —CH═CH—; Or a combination of these alkyl groups,

R ₁₀₆ is a substituted or unsubstituted alkyl group; Substituted or unsubstituted alkylaryl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted pyrimidinyl group; Substituted or unsubstituted pyridinyl group; Substituted or unsubstituted thiophenyl group; Substituted or unsubstituted furanyl group; Substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted phenyl group,

The substituted alkyl group in R ₁₀₆ is an alkyl group in which a hydrogen atom is substituted with a halogen atom or a cyano group with a substituent; An alkyl group wherein at least one non-adjacent CH ₂ group of the alkyl group is substituted with —O—, —CO—O—, —O—CO—, or —CH═CH—; Or a combination of these alkyl groups

The substituted alkylaryl group in R ₁₀₆ is an alkylaryl in which one or more non-adjacent CH ₂ groups of the alkylaryl group are substituted with -O-, -CO-O-, -O-CO-, or -CH = CH-. Ki)

(23)

(In Chemical Formula 23,

R ₁₁₁ is an aromatic diamine group; A diamine group substituted with a substituted or unsubstituted linear or branched alkylene group having 2 to 24 carbon atoms, or a combination thereof,

The substituted alkylene group in R ₁₁₁ is an alkylene group wherein a hydrogen atom is substituted with a halogen atom or a cyano group; At least one non-adjacent CH ₂ group of the alkylene group is substituted or unsubstituted arylene group, substituted or unsubstituted heteroarylene group, substituted or unsubstituted cycloalkylene group, substituted or unsubstituted heterocycloalkylene group, -O -, -CO-, -CO-O-, -O-CO-, -Si (CH ₃ ) ₂ -O-Si (CH ₃ ) _2- , -NR'-, -NR'-CO-, -CO —NR′—, —NR′—CO—O—, —O—CO—NR′—, —CH═CH—, —C≡C—, or —O—CO—O—, where R ′ is hydrogen. Or an alkylene group substituted with a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; Or a combination of these alkylene groups,

R ₁₁₂ is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, n ₁₁₂ is an integer of 0 to 4,

R ₁₁₃ and R ₁₁₄ are each independently a hydrogen atom; A halogen atom; Cyano; Or a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms,

The alkyl group substituted in R ₁₁₃ and R ₁₁₄ is an alkyl group in which a hydrogen atom is substituted with a halogen atom or a cyano group; An alkyl group wherein at least one non-adjacent CH ₂ group of the alkyl group is substituted with —O—, —CO—O—, —O—CO—, or —CH═CH—; Or a combination thereof is an alkyl group)

(D) Solvent

Liquid crystal photo-alignment agent according to an embodiment of the present invention includes a solvent.

As the solvent, any that can dissolve the polymer and the epoxy compound can be used.

The solvent is N-methyl-2-pyrrolidone, N, N-dimethyl acetamide, N, N-dimethyl formamide, dimethyl sulfoxide, γ-butyrolactone, and phenols such as metacresol, phenol, halogenated phenols, and the like. System solvents and the like can be used.

The solvent may further include an alcohol, a ketone, an ester, an ether, a hydrocarbon, a hydrocarbon or a halogenated hydrocarbon which is a poor solvent in an appropriate ratio within a range in which the polyimide polymer is not precipitated. This is because the poor solvents lower the surface energy of the liquid crystal aligning agent to improve spreadability and flatness during application.

The poor solvent may be used in the range of 1 to 90% by volume of the total solvent, and may be used in the range of 1 to 70% by volume.

Specific examples of the poor solvent include methanol, ethanol, isopropanol, cyclohexanol, ethylene glycol, propylene glycol, 1,4-butanediol, triethylene glycol, acetone, methyl ethyl ketone, cyclohexanone, methyl acetate, ethyl acetate, acetic acid Butyl, diethyl oxalate, malonic ester, diethyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol phenyl ether, ethylene glycol phenyl methyl ether, ethylene glycol phenyl ethyl ether, ethylene glycol dimethylethyl, diethylene Glycol dimethylethyl, diethylene glycol ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, ethylene glycol methyl ether acetate, ethylene glycol ethyl ether ace Tay , 4-hydroxy-4-methyl-2-pentanone, 2-hydroxy ethyl propionate, 2-hydroxy-2-methyl ethyl propionate, ethoxy acetate, ethyl hydroxy acetate, 2-hydroxy-3 Methyl butyrate methyl, 3-methoxy methyl propionate, 3-methoxy ethylpropionate, 3-ethoxy ethyl propionate, 3-ethoxy methyl propionate, methyl methoxy butanol, ethyl methoxy butanol, methyl ethoxy Butanol, ethyl ethoxy butanol, tetrahydrofuran, dichloromethane, 1,2-dichloroethane, 1,4-dichloro butane, trichloroethane, chlorobenzene, o-dichlorobenzene, hexane, heptane, octane, benzene, toluene, Xylene or these can be used in mixture of 1 or more types.

The content of the solvent in the liquid crystal photo-alignment agent is not particularly determined, but may be used so that the solid content of the liquid crystal photo-alignment agent is from 1 to 30% by weight. The content of the solvent according to another embodiment of the present invention may be used so that the solid content of the liquid crystal photo-alignment agent is 3 to 15% by weight, or may be used to be 5 to 10% by weight. When the content of the solid content is within the above range, the uniformity of the film can be properly maintained without being influenced by the surface of the substrate during printing, and the appropriate viscosity can be maintained, thereby reducing the uniformity of the film formed during printing due to the high viscosity. It can prevent, and can show appropriate transmittance | permeability.

Liquid crystal photoalignment film according to another embodiment of the present invention is prepared using the liquid crystal photoalignment agent.

The liquid crystal photo-alignment film can be formed by applying a liquid crystal photo-alignment agent to a substrate. Examples of the method for applying the liquid crystal photo-alignment agent to the substrate include a spin coat method, a flexographic printing method and an inkjet method. Among them, the flexographic printing method is excellent in uniformity of the formed coating film and can be easily enlarged, and therefore, it can be generally used.

The substrate can be used without particular limitation as long as it is a substrate having high transparency, and a plastic substrate such as a glass substrate or an acrylic substrate or a polycarbonate substrate can be used. In addition, by using a substrate on which an ITO electrode or the like for driving the liquid crystal is formed, the manufacturing process can be simplified.

The liquid crystal photo-alignment agent is uniformly applied to the substrate in order to increase the uniformity of the coating film, then to a temperature of room temperature to 200 ℃, according to another embodiment to a temperature of 30 to 150 ℃, according to another embodiment 40 to 120 Temporary drying may be carried out for 1 to 100 minutes at a temperature of ℃. By adjusting the volatilization degree of each component of the liquid crystal aligning agent through the temporary drying, a uniform and uneven coating film can be obtained.

Thereafter, baking is carried out at a temperature of 80 to 300 ° C or 120 to 280 ° C for 5 to 300 minutes to completely evaporate the solvent to form a liquid crystal photoalignment film.

The liquid crystal photoalignment film formed by the above method is used in a liquid crystal display without performing uniaxial alignment treatment by polarized ultraviolet irradiation or in some applications such as a vertical alignment film.

The liquid crystal photoalignment film according to the embodiment of the present invention may be subjected to uniaxial alignment treatment by exposing for 0.1 to 180 minutes at an energy of 10 mJ to 5000 mJ. As described above, when the uniaxial orientation treatment is performed while reducing the exposure intensity, the double bond included in the polyimide photopolymer may be completely removed.

Hereinafter, specific embodiments of the present invention will be described. However, the examples described below are merely to specifically illustrate or explain the present invention, and the present invention is not limited thereto.

In addition, the description is not described herein, so those skilled in the art that can be sufficiently technically inferred the description thereof will be omitted.

(Production example # 1: production of epoxy compound)

[Reaction Scheme 1]

An epoxy compound was prepared by the method shown in Scheme 1.

One equivalent of the compound (24) was dissolved in methylene clyde and stirred at room temperature. To the solution was added 1 equivalent of glycidol, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide) (EDC) 1 equivalent dissolved in HCl and 1.2 equivalents of 3-dimethylamino propylamine (DMAP). , Was stirred for 16 hours.

The reaction was terminated by thin layer chromatography (diffusion solvent-hexane: ethyl acetate = 2: 1 volume ratio), and the reaction solution was concentrated.

The concentrated reaction solution was suspended with ethyl acetate and filtered through a silica gel pad to remove salts and inorganics. The obtained filtrate was concentrated, and the concentrate was purified using a silica gel column and a diffusion solvent (hexane: methylene chloride: ethyl acetate = 1: 1: 0.5 volume ratio). The purified product was then concentrated, the concentrated residue was washed by suspension stirring with ethyl alcohol, filtered and dried to prepare an epoxy compound of formula 2 as the desired product.

¹ H NMR of the prepared epoxy compound was measured and the results are shown in FIG. 1.

In addition, in order to determine the purity of the prepared epoxy compound, the liquid chromatography (HPLC, High Performance Liquid Chromatography) measurement results of the prepared epoxy compound are shown in FIG. 2. As shown in FIG. 2, since only the peak corresponding to the target product appeared large, it can be seen that the target product was obtained with high purity with little impurities.

Preparation Example # 2 Preparation of Polyamic Acid (PAA-1)

A functional diamine 3,5-diaminophenyldecyl succinimide represented by the following formula (25) while passing nitrogen through a four-necked flask equipped with a stirrer, a thermostat, a nitrogen gas injection device, a fan and a cooler 0.1 mmol of 3,5-Diaminophenyldecyl succinimide) was added, and N-methyl-2-pyrrolidone (NMP) was added thereto to prepare a mixed solution.

(25)

1.0 mmol of 1,2,3,4-cyclobutanetetracarboxylic dianhydride in solid state was added to the mixed solution, followed by vigorous stirring. At this time, the solid content is 20% by weight, the reaction was carried out for 10 hours while maintaining the temperature at 30 ℃ ~ 50 ℃ to prepare a polyamic acid resin. A mixed organic solvent of N-methyl-2-pyrrolidone and γ-butyrolactone, which are organic solvents, was added to the prepared polyamic acid resin, and stirred at room temperature for 24 hours to give a polyamic acid solution having a solid content of 6% by weight (PAA- 1) was prepared.

(Production example # 3: preparation of polyimide polymer (SPI-1))

Into a four-necked flask equipped with a stirrer, a temperature controller, a nitrogen gas injector, and a cooler, 0.8 mol of phenylenediamine and 0.2 mol of diamine 3,5-diaminophenyldecyl succinimide represented by Chemical Formula 25 were added thereto. , N-methyl-2-pyrrolidone was added to prepare a mixed solution.

4,10-dioxa-tricyclo [6.3.1.02,7] dodecane-3,5 instead of 1,2 mol of 1,2,3,4-cyclobutanetetracarboxylic dianhydride in the mixed solution A polyamic acid solution (PAA-2) was prepared in the same manner as in Preparation Example 1, except that 9,11-tetraon was used. The solid content at this time is 20% by weight, the reaction was carried out for 10 hours while maintaining a temperature of 30 ℃ 50 50 ℃ to prepare a polyamic acid solution.

3.0 mol of acetic anhydride and 5.0 mol of pyridine were added to the prepared polyamic acid solution, and the temperature was raised to 80 ° C., followed by reaction for 6 hours, and removal of the catalyst and solvent through vacuum distillation to give a solid content of 20% by weight. Polyimide resin was prepared.

A mixed organic solvent of N-methyl-2-pyrrolidone 인 and γ-butyrolactone, which are organic solvents, was added to the soluble polyimide resin thus prepared, and stirred at room temperature for 24 hours to give a 6% by weight polyimide solution (SPI). -1) was prepared.

(Production of Liquid Crystal Photocolon)

(Example 1)

To 80 g of PAA-1 'solution of 6% by weight of solid content obtained in Preparation Example 2, 20 g of SPI-1 solution of 6% by weight of solid content obtained in Preparation Example 3 was added to prepare a polymer liquid. The epoxy compound prepared in Preparation Example 1 was added to the polymer liquid, stirred for 24 hours while passing nitrogen, and filtered through a filter having a particle size of 0.1 μm to obtain a liquid crystal photoalignment agent having a solid content of 6% by weight (hereinafter referred to as PSPI-1). do). The use amount of the epoxy compound was 6 parts by weight based on 100 parts by weight of the total solids of the PAA-1 solution, SPI-1 solution and the epoxy compound.

(Example 2)

A liquid crystal light crystal having a solid content of 6% by weight in the same manner as in Example 1, except that the amount of the epoxy compound was changed to 10 parts by weight based on 100 parts by weight of the total solids of the PAA-1 solution, the SPI-1 solution and the epoxy compound. A fragrance was obtained (hereinafter referred to as PSPI-2).

Example 3

A liquid crystal light crystal having a solid content of 6% by weight in the same manner as in Example 1, except that the amount of the epoxy compound was changed to 20 parts by weight based on 100 parts by weight of the total solids of the PAA-1 solution, the SPI-1 solution and the epoxy compound. A fragrance was obtained (hereinafter referred to as PSPI-3).

Example 4

A liquid crystal light crystal having a solid content of 6% by weight in the same manner as in Example 1, except that the amount of the epoxy compound was changed to 8 parts by weight based on 100 parts by weight of the total solids of the PAA-1 solution, the SPI-1 solution and the epoxy compound. A fragrance was obtained (hereinafter referred to as PSPI-4).

Example 5

A liquid crystal light crystal having a solid content of 6% by weight in the same manner as in Example 1, except that the amount of the epoxy compound was changed to 12 parts by weight based on 100 parts by weight of the total solids of the PAA-1 solution, the SPI-1 solution and the epoxy compound. A fragrance was obtained (hereinafter referred to as PSPI-5).

Example 6

A liquid crystal light crystal having a solid content of 6% by weight in the same manner as in Example 1, except that the amount of the epoxy compound was changed to 15 parts by weight based on 100 parts by weight of the total solids of the PAA-1 solution, the SPI-1 solution and the epoxy compound. A fragrance was obtained (hereinafter referred to as PSPI-6).

Example 7

A liquid crystal light crystal having a solid content of 6% by weight in the same manner as in Example 1, except that the amount of the epoxy compound was changed to 25 parts by weight based on 100 parts by weight of the total solids of the PAA-1 solution, the SPI-1 solution and the epoxy compound. A fragrance was obtained (hereinafter referred to as PSPI-7).

(Example 8)

A liquid crystal light crystal having a solid content of 6% by weight in the same manner as in Example 1, except that the amount of the epoxy compound was changed to 30 parts by weight based on 100 parts by weight of the total solids of the PAA-1 solution, the SPI-1 solution and the epoxy compound. The fragrance was obtained (hereinafter referred to as PSPI-8).

(Comparative Example 1)

100 g of the 6% by weight PAA-1 solution obtained in Preparation Example 2 was stirred for 24 hours while passing through nitrogen, followed by filtration through a filter having a particle size of 0.1 μm to obtain a liquid crystal aligning agent having a solid content of 6% by weight (hereinafter referred to as PSPI-10). do).

(Comparative Example 2)

100 g of SPI-1 solution of 6% by weight of solid content obtained in Preparation Example 3 was stirred for 24 hours while passing through nitrogen, followed by filtration with a filter having a particle size of 0.1 μm to obtain a liquid crystal aligning agent of 6% by weight of solid content (hereinafter referred to as PSPI-11). do).

(Comparative Example 3)

20 g of 6% by weight of the SPI-1 solution of 6% by weight of solids obtained in Preparation Example 3 was added to 80 g of PAA-1 solution of 6% by weight of solids obtained in Preparation Example 2, followed by stirring for 24 hours while passing nitrogen. Filtration gave a liquid crystal aligning agent having a solid content of 6% by weight (hereinafter referred to as PSPI-12).

(Evaluation of Printability and Finish Coating Uniformity)

One with a washing ITO deposited on the glass substrate, using the above Examples 1 to 8 and Comparative Example 1, the alignment film a liquid crystal halo hyangje prepared in for three presses (CZ ^200? Nakan社) for flexographic printing after the The printed substrate was allowed to stand on a 50-90 ° C. hotplate for 2-5 minutes to effect dry drying of the coating film.

After the substrate was temporarily dried, the substrate was baked on a hot plate at 200 to 230 ° C. for 10 to 30 minutes, and then exposed at an energy of 10 mJ to 5000 mJ for 0.1 to 180 minutes to prepare a substrate having a liquid crystal photoalignment film.

The film surface of the liquid crystal alignment layers naked eye, and an electron microscope ^(MX50? Olympus社) the substrate surface printing over the (center of the end portion) sex (pinhole (Pinhole) and staining) and had a film to measure the thickness change of the coating film through The results are shown in Table 1 below.

In Table 1 below, printability is good when the pinhole is 0 to 3, and when the case is 3 to 5, it is usually marked as bad when more than 6, the stain is good when not occurred, poorly marked as poor when the coating film uniform The case where the thickness deviation was less than 0.005 micrometer was good, the case where it was 0.005-0.01 micrometer was considered normal, and the case where it exceeded 0.01 micrometer was marked as bad.

(Liquid crystal orientation of the liquid crystal photoalignment film)

In order to evaluate the liquid crystal aligning property of the liquid crystal photoalignment agent, the liquid crystal cell was produced and used. The manufacture of the liquid crystal cell is as follows.

The ITO glass substrate was patterned using a photolithography process to remove other portions of ITO, leaving only 1.5 cm × 1.5 cm square ITO shapes and electrode ITO shapes for voltage application.

The liquid crystal photo-alignment agent prepared in Examples 1 to 8 and Comparative Examples 1 to 3 was applied to the patterned ITO substrate, spin-coated to 0.1 μm thickness, and then subjected to curing at 70 ° C. and 210 ° C.

The two I substrates subjected to the curing process using an exposure machine (UIS-S2021J7-YD01, Ushio LPUV) under a certain angle and a constant energy are exposed so that the exposure directions are opposite to each other (90 degrees for VA mode). Thereafter, square ITO shapes were joined up and down consistently while maintaining a cell gap of 4.75 mu m. In the exposure, a light source used a 2kW deep UV ramp (UXM-2000).

After filling the liquid crystal in the cell made in this way, the liquid crystal alignment was observed using an orthogonally polarized optical microscope, and the results are summarized in Table 1 below.

(Electrical and Optical Properties of Liquid Crystal Photoalignment Films)

The electrical and optical properties of the liquid crystal photoalignment film were evaluated by measuring voltage-transmittance curve, voltage holding ratio, and residual DC voltage using a liquid crystal cell having a 4.75 μm cell gap.

The voltage-transmission curve, the voltage holding ratio, and the electrical and optical characteristics of the residual DC voltage are briefly described as follows.

The voltage-transmittance curve is one of the important electrical and optical characteristics, which is one of the characteristics for determining the driving voltage of the liquid crystal display device. The curve is normalized with the amount of light in the state at 0%.

The voltage retention ratio refers to the extent to which the liquid crystal layer in the state of floating with the external power source maintains the charged voltage during the non-selection period in the active driving type TFT-LCD, and a value close to 100% is ideal.

The residual DC voltage refers to a voltage applied to the liquid crystal layer even when no impurities are applied to the alignment layer by the impurities of the ionized liquid crystal layer, and the lower the better. As a method of measuring the residual DC voltage, a method using flicker and a method using a capacitance change curve (C-V) of the liquid crystal layer according to DC voltage are common.

The electrical and optical properties of the liquid crystal photoalignment film using the liquid crystal cell are shown in Table 1 below.

sample Printability Coating
Uniformity ore
Orientation Voltage-Transmittance Voltage retention rate (%) Residual DC
(by CV) Room temperature
(60 Hz) Room temperature
(10 Hz) Example 1 Good Good Good Good 99.42 98.15 142 Example 2 Good Good Good Good 99.25 98.12 138 Example 3 Good Good Good Good 99.22 98.23 154 Example 4 Good Good Good Good 99.52 98.26 106 Example 5 Good Good Good Good 99.48 98.18 72 Example 6 Good Good Good Good 99.56 99.16 83 Example 7 Good Good Good Good 99.59 99.15 69 Example # 8 Good Good Good Good 99.67 99.12 72 Comparative Example 1 Good Good Bad Good 98.52 92.11 365 Comparative Example 2 Good Good Bad Good 98.48 94.30 480 Comparative Example 3 Good Good Bad Good 98.51 92.23 652

Referring to Table 1 above, it can be seen that the liquid crystal photoalignment agents of Examples 1 to 8 are more excellent in printability, coating uniformity, voltage transmittance, voltage holding ratio and residual DC characteristics.

The voltage holding ratio and the residual DC serve as a criterion for evaluating the afterimage characteristic of the liquid crystal photoalignment film, and the higher the voltage holding ratio and the lower the residual DC, the better the afterimage characteristic. Therefore, it can be seen that the liquid crystal photoalignment agent prepared in Examples 1 to 8 is superior to the afterimage property than the liquid crystal photoalignment agent prepared in Comparative Examples 1 to 3.

The present invention is not limited to the above embodiments, but may be manufactured in various forms, and a person skilled in the art to which the present invention pertains has another specific form without changing the technical spirit or essential features of the present invention. It will be appreciated that the present invention may be practiced as. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive.

1 is a graph showing the ¹ H NMR measurement of the epoxy compound prepared in Preparation Example 1 of the present invention.

Figure 2 is a graph showing the measurement of the HPLC of the epoxy compound prepared in Preparation Example 1 of the present invention.

Claims (9)

Epoxy compound for liquid crystal photo-alignment agent represented by the following formula (1). [Formula 1]

(In the formula 1, R ₁ and R ₂ are each independently a hydrogen atom; Or a substituted or unsubstituted alkyl group, R ₃ , R ₄ and R ₅ are each independently a hydrogen atom; A halogen group; Or a substituted or unsubstituted alkyl group, n is 1 to 20.) The method of claim 1, R ₁ and R ₂ are each independently a hydrogen atom, R ₃ , R ₄ and R ₅ are each independently a halogen atom, N is 2, the epoxy compound. The method of claim 1, The epoxy compound is an epoxy compound that is at least one of the compounds represented by the formula 2 to 3. [Formula 2]

(3)

An epoxy compound represented by Formula 1; And Polymers that are polyamic acids, polyimide polymers, or mixtures thereof Liquid crystal photo-alignment agent comprising a. [Formula 1]

(In the formula 1, R ₁ and R ₂ are each independently a hydrogen atom; Or a substituted or unsubstituted alkyl group, R ₃ , R ₄ and R ₅ are each independently a hydrogen atom; A halogen group; Or a substituted or unsubstituted alkyl group, n is 1 to 20.) 5. The method of claim 4, The content of the epoxy compound is a liquid crystal aligning agent is 0.01 to 60 parts by weight based on the total amount of 100 parts by weight of the epoxy compound and the polymer. 5. The method of claim 4, The epoxy compound is a liquid crystal aligning agent is at least one of the compounds represented by the formula (2) to # 3. [Formula 2]

(3)

5. The method of claim 4, The polyamic acid is a liquid crystal photo-alignment agent is represented by the following formula (5). [Chemical Formula 5]

(In Chemical Formula 5, R ₃₁ is a tetravalent organic group derived from an aliphatic cyclic dianhydride or an aromatic acid dianhydride, R ₃₂ is a divalent organic group derived from diamine.) 5. The method of claim 4, The polyimide polymer is a liquid crystal photo-alignment agent is represented by the following formula (6). [Formula 6]

(In Chemical Formula 6, R ₃₃ is a tetravalent organic group derived from an aliphatic cyclic acid dianhydride or an aromatic acid dianhydride, R ₃₄ is a divalent organic group derived from diamine; Or a divalent organic group derived from a photodiamine selected from coumarin photodiamine, chalcone photodiamine, and cinnamate photodiamine.) A liquid crystal photoalignment film prepared by applying the liquid crystal photoalignment agent according to any one of claims 4 to 8 to a substrate.

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