KR20090061376A - Photoalignment agent of liquid crystal, photoalignment film of liquid crystal including the same, and liquid crystal display including the same - Google Patents

Abstract

A photoalignment agent is provided to ensure excellent reliability relating to after image and excellent liquid crystal orientation, to stabilize vertical alignment power and to secure stability to the change of a processing condition. A photoalignment agent, comprises based on solid portion, a polysiloxanepolymer 10-99.9 weight% and a polyimide photopolymer 0.1-90 weight% represented by chemical formula 4. The polyorgansiloxane polymer is obtained by polymerizing any one alkoxysilane compound selected from the group consisting of compounds represented by chemical formula 1: Si(R1)4, chemical formula 2: Si(R2)4, chemical formula 3: (R4)3Si-(R3)n-Si(R4)3, and combinations thereof. The solid portion of the photoalignment agent is 1-30 weight%.

Description

Liquid crystal photoalignment agent, a liquid crystal photoalignment film including the same, and a liquid crystal display device including the same TECHNICAL FIELD OF THE LIQUID CRYSTAL

The present invention relates to a liquid crystal photoalignment agent used in a liquid crystal display device, a liquid crystal photoalignment film including the same, and a liquid crystal display device including the same, and more particularly, long life, stable pretilt angle maintenance, and afterimage characteristics. The present invention relates to a liquid crystal photoalignment agent which is improved and is excellent in liquid crystal alignment and chemical resistance.

A 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 arrangement of the liquid crystal molecules, so that the liquid crystal is moved by an electric field to form an image when the image is formed. In general, in order to obtain uniform brightness and high contrast ratio, it is essential to uniformly align the liquid crystal.

Conventionally, a rubbing method is used in which a polymer film such as polyimide is applied to a substrate such as glass, and the surface is rubbed in a predetermined direction with fibers such as nylon or polyester as a conventional method for orienting liquid crystals. 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) to a polymer film by light irradiation instead of friction and arranging liquid crystals using the same has been studied.

As a material that can be used in the photo-alignment method, polymers containing optical functional groups such as azobenzene, cumarine, chalcone, chalcone and cinnamate have been developed. These polymers are anisotropically reacted by photoisomerization or photocrosslinking by polarized light irradiation, and thus anisotropy is generated on the surface of the polymer to induce molecular alignment of the liquid crystal in one direction.

In order to apply such liquid crystal alignment film materials to the liquid crystal display device substantially, optical stability and thermal stability should be excellent and there should be no afterimage. However, conventionally known photo-orientation materials present many problems in this respect.

On the other hand, the conventional liquid crystal photo-alignment film material is mostly a polymer type, and has a photofunctional group capable of inducing optical anisotropy such as azobenzene or cinnamate as a side group in the polymer main chain. When using such a polymer liquid crystal photoalignment film material, not only a large amount of light energy is required to induce anisotropy, but also a large number of unreacted photofunctional groups that remain unreacted may be used for thermal stability, optical stability, and electro-optical characteristics. It can have a serious effect.

An object of the present invention is excellent in reliability associated with the afterimage, stable vertical alignment force, excellent liquid crystal alignment, the vertical alignment force is not lowered by the liquid crystal dropping of the one drop filling (ODF) method, It is to provide a liquid crystal photoalignment agent for a wide viewing angle stable to changes in process conditions.

Another object of the present invention is to provide a liquid crystal photoalignment film comprising the liquid crystal photoalignment agent.

Still another object of the present invention is to provide a liquid crystal display device including the liquid crystal photoalignment film.

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

In order to solve the above technical problem, according to one embodiment of the present invention, a polysiloxane prepared by polymerizing any one alkoxy silane compound selected from the group consisting of compounds represented by the following formulas (1) to (3), and combinations thereof It provides a liquid crystal photo-alignment agent comprising a polymer and a polyimide photopolymer represented by the following formula (4).

[Formula 1]

Si (R ₁ ) ₄

(In Formula 1,

The four R ₁ are each independently a substituent selected from the group consisting of hydroxy, alkoxy having 1 to 5 carbon atoms, and an aryloxy group having 6 to 20 carbon atoms)

[Formula 2]

Si (R ₂ ) ₄

(In Formula 2,

Each of the four R ₂ is independently a hydrogen atom, an alkyl group or fluoroalkyl group having 1 to 20 carbon atoms, an aryl group or fluoroaryl group having 6 to 20 carbon atoms, hydroxy, alkoxy having 1 to 5 carbon atoms, and 6 to 20 carbon atoms Any substituent selected from the group consisting of an aryloxy group,

One or _two of the four R ₂ are each independently selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 20 carbon atoms or a fluoroalkyl group, an aryl group having 6 to 20 carbon atoms or a fluoraryl group, and 2 or 3 are hydroxy Oxy, alkoxy having 1 to 5 carbon atoms, and an aryloxy group having 6 to 20 carbon atoms).

[Formula 3]

(R ₄ ) ₃ Si- (R ₃ ) _n -Si (R ₄ ) ₃

(In Chemical Formula 3,

R ₃ is any one selected from the group consisting of an alkylene group or a fluoroalkylene group having 1 to 8 carbon atoms, an arylene group or a fluorarylene group having 6 to 20 carbon atoms, and n is an integer of 0 to 8,

Each of the six R _{4 's} is independently a substituent selected from the group consisting of hydroxy, alkoxy having 1 to 5 carbon atoms, and aryloxy group having 6 to 20 carbon atoms)

[Formula 4]

(In Formula 4,

R ₅ is a tetravalent organic group derived from any one acid dianhydride selected from the group consisting of aliphatic cyclic dianhydrides and aromatic acid dianhydrides,

R ₆ is a divalent organic group derived from any one photodiamine selected from the group consisting of a cumarine photodiamine, a chalcone photodiamine, and a cinnamate photodiamine.

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

According to another embodiment of the present invention, a liquid crystal display including the liquid crystal photoalignment layer is provided.

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

The liquid crystal photoalignment agent of the present invention is excellent in optical stability and thermal stability, and excellent in reliability associated with afterimages. In particular, the liquid crystal photo-alignment agent has a long lifespan, stable pretilt angle retention, improved afterimage characteristics, excellent liquid crystal alignment and chemical resistance, etc., thereby improving the display quality of a liquid crystal display (LCD), and thus for LCD TVs. It is suitable for use as a liquid crystal photoalignment agent. In addition, the alignment film characteristics of the liquid crystal photoalignment film of the present invention are not lowered by a process such as liquid crystal dropping or washing in the LCD panel manufacturing process.

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

According to one embodiment of the present invention, a polysiloxane polymer prepared by polymerizing any one alkoxy silane compound selected from the group consisting of a compound represented by the following Chemical Formulas 1 to 3, and a combination thereof and a poly represented by the following Chemical Formula 4 It provides a liquid crystal photo-alignment agent comprising a mid photopolymer.

[Formula 1]

Si (R ₁ ) ₄

(In Formula 1,

The four R ₁ are each independently a substituent selected from the group consisting of hydroxy, alkoxy having 1 to 5 carbon atoms, and an aryloxy group having 6 to 20 carbon atoms)

[Formula 2]

Si (R ₂ ) ₄

(In Formula 2,

Each of the four R ₂ is independently a hydrogen atom, an alkyl group or fluoroalkyl group having 1 to 20 carbon atoms, an aryl group or fluoroaryl group having 6 to 20 carbon atoms, hydroxy, alkoxy having 1 to 5 carbon atoms, and 6 to 20 carbon atoms Any substituent selected from the group consisting of an aryloxy group,

One or _two of the four R ₂ are each independently selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 20 carbon atoms or a fluoroalkyl group, an aryl group having 6 to 20 carbon atoms or a fluoraryl group, and 2 or 3 are hydroxy Oxy, alkoxy having 1 to 5 carbon atoms, and an aryloxy group having 6 to 20 carbon atoms).

[Formula 3]

(R ₄ ) ₃ Si- (R ₃ ) _n -Si (R ₄ ) ₃

(In Chemical Formula 3,

R ₃ is any one selected from the group consisting of an alkylene group or a fluoroalkylene group having 1 to 8 carbon atoms, an arylene group or a fluorarylene group having 6 to 20 carbon atoms, and n is an integer of 0 to 8,

Each of the six R _{4 's} is independently a substituent selected from the group consisting of hydroxy, alkoxy having 1 to 5 carbon atoms, and aryloxy group having 6 to 20 carbon atoms)

[Formula 4]

(In Formula 4,

R ₅ is a tetravalent organic group derived from any one acid dianhydride selected from the group consisting of aliphatic cyclic dianhydrides and aromatic acid dianhydrides,

R ₆ is a divalent organic group derived from any one photodiamine selected from the group consisting of a cumarine photodiamine, a chalcone photodiamine, and a cinnamate photodiamine.

Substituted herein, unless specified otherwise, a hydrogen atom is a halogen group, an alkyl group of 1 to 30 carbon atoms, a haloalkyl group of 1 to 30 carbon atoms, an aryl group of 6 to 30 carbon atoms, a heteroaryl group of 2 to 30 carbon atoms, carbon atoms It means substituted with any one substituent selected from the group consisting of 1 to 20 alkoxy groups, and combinations thereof.

In addition, in the present specification, hetero means a carbon atom substituted with any one hetero atom selected from the group consisting of N, O, S, and P unless otherwise specified.

In Formula 1, the alkoxy group is preferably an alkoxy group having 1 to 5 carbon atoms, such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, or a pentoxy group. Preferred examples of the alkoxy silane compound represented by the formula (1) include tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane, tetrabutoxysilane and the like, and furthermore, tetramethoxysilane or tetraethoxysilane It can be used preferably. The compounds may also be used in combination as a mixture of two or more.

When the polysiloxane is polymerized with the tetraalkoxy silane represented by the above formula (1), the degree of crosslinking of the polymer becomes dense and stable, and the reliability of the alignment layer can be greatly increased, and it is preferable to introduce a high content into the polymer. However, when the tetraalkoxy silane is included in a high content, the chemical resistance-solvent resistance of the alignment layer is increased, thereby making it insoluble in the stripper solvent and thus making it impossible to rework.

In Formula 2, one of the four R _{2 is} selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 20 carbon atoms or a fluoroalkyl group, an aryl group having 6 to 20 carbon atoms, or a fluoroaryl group, and three are hydroxy and 1 carbon atom. Alkoxy of 5 to 5, and an aryloxy group having 6 to 20 carbon atoms. Alternatively, _two of the four R ₂ may be each independently selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 20 carbon atoms or a fluoroalkyl group, an aryl group having 6 to 20 carbon atoms, or a fluoraryl group, and two may be each independently Hydroxy, alkoxy having 1 to 5 carbon atoms, and an aryloxy group having 6 to 20 carbon atoms.

When said R <_2> is a C1-C20 alkyl group or a fluoroalkyl group, it is more preferable that the said alkyl group is a C6-C20 long chain alkyl group.

As the unsubstituted alkyl group, a hexyl group, heptyl group, octyl group, dodecyl group, hexadecyl group, octadecyl group or the like can be preferably used. As the fluoroalkyl group, trifluoropropyl group, heptafluoropentyl group, heptafluoroisopentyl group, tridecafluorooctyl group, or heptadecafluorodecyl group can be preferably used.

Preferred examples of the alkoxy silane represented by Formula 2 are hexyltrimethoxysilane, hexyltriethoxysilane, heptyltrimethoxysilane, heptyltriethoxysilane, octyltrimethoxy silane, octyltriethoxysilane, dodecyl Unsubstituted alkyltrialkoxy silanes such as trimethoxysilane, dodecyltriethoxysilane, hexadecyltrimethoxysilane, hexadecyltriethoxysilane, octadecyltrimethoxysilane, or octadecyltriethoxysilane are preferably used. Can be used.

In addition, preferred examples of the alkoxy silane represented by Formula 2 include trifluoropropyltrimethoxysilane, trifluoropropyltriethoxysilane, heptafluoropentyltrimethoxysilane, heptafluoropentyltriethoxysilane, Fluoroalkyl trialkoxy silanes such as tridecafluorooctyltrimethoxysilane, tridecafluorooctyltriethoxysilane, heptadecafluorodecyltrimethoxysilane, or heptadecafluorodecyltriethoxysilane are preferred. Can be used.

The trialkoxy silane having the long-chain alkyl group plays a key function of determining the alignment and pretilt angle of the liquid crystal, but when used in an appropriate amount or more, the electrical properties and the reliability of the alignment layer are deteriorated, so that the liquid crystal alignment characteristics are not compromised. It is desirable to minimize the amount of use.

In the formula (3), the alkoxy group is preferably an alkoxy group having 1 to 5 carbon atoms, such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, or a pentoxy group.

R ₃ is any one selected from the group consisting of an alkylene group or fluoroalkylene group having 1 to 8 carbon atoms, and an arylene group or fluorarylene group having 6 to 20 carbon atoms, and n is preferably an integer of 0 to 8. More preferably, R ₃ is a methylene group or a phenylene group.

Preferred examples of the alkoxy silane compound represented by Formula 3 include hexa methoxy disilane, bis trimethoxy disilyl methane, bis trimethoxy dissilyl ethane, bis trimethoxy dissilyl propane, bis trimethoxy dissilyl butane , Bis trimethoxy disilyl pentane, bis trimethoxy disilyl hexane, bis trimethoxy disilyl heptane, bis trimethoxy dissilyl octane, bis triethoxy dissilyl methane, bis triethoxy dissilyl ethane, bis Triethoxy dissilyl propane, bis triethoxy disilyl butane, bis triethoxy dissilyl pentane, bis triethoxy dissilyl hexane, bis triethoxy dissilyl heptane, bis triethoxy dissilyl octane, bis trie Toxy disilyl benzene, etc. can be used preferably.

The polyimide photopolymer represented by Formula 4 may be synthesized from any one acid dianhydride selected from the group consisting of at least one photodiamine, aliphatic cyclic acid dianhydride, aromatic acid dianhydride, and combinations thereof. Since a method of preparing a polyimide photopolymer by copolymerizing the photodiamine and an acid dianhydride is well known in the art, a detailed description thereof will be omitted.

Aliphatic cyclic acid dianhydrides used in the preparation of the polyimide photopolymer 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-cyclopentanetetra Carboxylic dianhydride (CPDA), 1,2,4,5-cyclohexanetetracarboxylic dianhydride (CHDA), 1,2,4-tricarboxy-3-methylcarboxy cyclopentane dianhydride, 1,2 Any one compound selected from the group consisting of, 3,4-tetracarboxy cyclopentane anhydride, and combinations thereof may be used, but is not limited thereto.

The tetravalent organic group derived from the aliphatic cyclic acid dianhydride may have any one structure selected from the group consisting of compounds represented by the following Formulas 5 to 9, and combinations thereof.

[Formula 5] [Formula 6] [Formula 7]

[Formula 8] [Formula 9]

(In Chemical Formulas 5 to 9,

R ₁₀ is any one selected from the group consisting of a substituted or unsubstituted C1-20 alkyl group, a substituted or unsubstituted C1-30 aryl group, and a substituted or unsubstituted C2-30 heteroaryl group and the substituent group, and wherein n ₁₀ is an integer of 0 to 3,

R ₁₁ to R ₁₇ are each independently a hydrogen atom, a substituted or unsubstituted C1-20 alkyl group, a substituted or unsubstituted C1-30 aryl group, and a substituted or unsubstituted C2-30 hetero Is any substituent selected from the group consisting of aryl groups)

Aromatic acid dianhydrides used in the production of the polyimide photopolymer include pyromellitic dianhydride (PMDA), nonphthalic dianhydride (BPDA), oxydiphthalic dianhydride (ODPA), benzophenonetetracarboxylic dianhydride (BTDA), Hexafluoroisopropylidenediphthalic anhydride (6-FDA), and any one compound selected from the group consisting of a combination thereof may be used, but is not limited thereto.

The tetravalent organic group derived from the aromatic acid dianhydride may have any one structure selected from the group consisting of a compound represented by Formula 10, a compound represented by Formula 11, and a combination thereof.

[Formula 10] [Formula 11]

(In Chemical Formula 10, and Formula 11,

R ₂₁ and R ₂₂ are each independently a hydrogen atom, a substituted or unsubstituted C1-20 alkyl group, a substituted or unsubstituted C1-30 aryl group, and a substituted or unsubstituted C2-30 hetero Any substituent selected from the group consisting of an aryl group,

R ₂₄ and R ₂₅ are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 1 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. One substituent selected from the group consisting of, wherein n ₂₄ , and n ₂₅ are each independently an integer of 0 to 3,

R ₂₃ is a substituted or unsubstituted alkylene group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 30 carbon atoms, and substituted or unsubstituted carbon atoms such as O, CO, and C (CF ₃ ) _2. Any one selected from the group consisting of 2 to 30 heterocycloalkylene groups, and n ₂₃ is an integer of 0 or 1)

The photodiamine may be preferably any one selected from the group consisting of coumarin-based photodiamine, chalcone-based photodiamine, cinnamate-based photodiamine, and combinations thereof.

As the cinnamate photodiamine, any one compound selected from the group consisting of a compound represented by the following Chemical Formula 12, a compound represented by the following Chemical Formula 13, and a combination thereof may be preferably used. As the compound represented by the following formula (14) can be preferably used, the compound represented by the following formula (15) can be preferably used as the coumarin-based photodiamine.

[Formula 12]

(In Chemical Formula 12,

R ₇₁ is selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms Which is any substituent,

R ₇₂ is any one selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. Is a substituent of, wherein n ₇₂ is an integer of 0 to 3)

[Formula 13]

(In Chemical Formula 13,

R ₇₇ is any one substituent selected from the group consisting of an aromatic diamine group, a diamine group including a substituted or unsubstituted linear or branched alkylene group having 1 to 24 carbon atoms, and a combination thereof,

The substituted alkylene group in R ₇₇ is an alkylene group in which a hydrogen atom is substituted with any substituent selected from the group consisting of a halogen atom and a cyano group; One or more non-adjacent CH ₂ groups of the alkylene group are substituted or unsubstituted arylene groups having 2 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups having 2 to 30 carbon atoms, and substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms. Alkylene group, substituted or unsubstituted heterocycloalkylene group having 2 to 30 carbon atoms, -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'-, -NR'-, -CO —NR′—, —CH═CH—, —C≡C—, and —O—CO—O—, wherein R ′ is a hydrogen atom and a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms An alkylene group substituted with any substituent selected from the group consisting of; And any one alkylene group selected from the group consisting of a combination thereof,

R ₇₄ is any one selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 1 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. One substituent, n ₇₄ is an integer of 0 to 4,

R ₇₅ and R ₇₆ are each independently a substituent selected from a hydrogen atom, a halogen atom, a cyano group, and a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms,

The alkyl group substituted in R ₇₅ and R ₇₆ is an alkyl group wherein a hydrogen atom is substituted with any substituent selected from the group consisting of a hetero atom and a cyano group; An alkyl group wherein at least one non-adjacent CH ₂ group of the alkyl group is substituted with any one substituent selected from the group consisting of -O-, -CO-O-, -O-CO-, and -CH = CH-; And any one alkyl group selected from the group consisting of a combination thereof,

R ₇₃ is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylaryl group having 7 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted Substituted pyrimidinyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted thiophenyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted naphthyl group, and substituted or unsubstituted phenyl group. Any one substituent is selected,

The alkyl group substituted in R ₇₃ is an alkyl group in which a hydrogen atom is substituted with any substituent selected from the group consisting of halogen and cyano group; An alkyl group wherein at least one non-adjacent CH ₂ group of the alkyl group is substituted with any one substituent selected from the group consisting of -O-, -CO-O-, -O-CO-, and -CH = CH-; And any one alkyl group selected from the group consisting of a combination thereof,

The substituted alkylaryl group for R _{73 is selected} from the group consisting of -O-, -CO-O-, -O-CO-, and -CH = CH-, in which at least one non-adjacent CH ₂ group of the alkylaryl group is selected. An alkylaryl group substituted with any one substituent)

[Formula 14]

(In Formula 14,

R ₈₁ is any substituent selected from the group consisting of an aromatic diamine group, a diamine group substituted with a substituted or unsubstituted linear or branched alkylene group having 1 to 24 carbon atoms, and a combination thereof,

The alkylene substituted at R ₈₁ is an alkylene group in which a hydrogen atom is substituted with any substituent selected from the group consisting of a halogen atom and a cyano group; One or more non-adjacent CH ₂ groups of the alkylene group are substituted or unsubstituted arylene groups having 2 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups having 2 to 30 carbon atoms, and substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms. Alkylene group, substituted or unsubstituted heterocycloalkylene group having 2 to 30 carbon atoms, -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'-, -NR'-, -CO —NR′—, —CH═CH—, —C≡C—, and —O—CO—O—, wherein R ′ is a hydrogen atom and a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms An alkylene group substituted with any one substituent selected from the group consisting of; And any one alkylene group selected from the group consisting of a combination thereof,

R ₈₂ and R ₈₅ are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 1 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. One substituent selected from the group consisting of, n ₈₂ , and n ₈₅ are each independently an integer of 0 to 4,

R ₈₃ and R ₈₄ are each independently any substituent selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, and a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms,

The alkyl group substituted in R ₈₃ and R ₈₄ is an alkyl group wherein a hydrogen atom is substituted with any substituent selected from the group consisting of a halogen atom and a cyano group; An alkyl group wherein at least one non-adjacent CH ₂ group of the alkyl group is substituted with any one substituent selected from the group consisting of -O-, -CO-O-, -O-CO-, and -CH = CH-; And any one alkyl group selected from the group consisting of a combination thereof,

R ₈₆ is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylaryl group having 7 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted Selected pyrimidinyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted thiophenyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted naphthyl group, and substituted or unsubstituted phenyl group. Which is any substituent,

The alkyl group substituted in R ₈₆ is an alkyl group in which a hydrogen atom is substituted with any substituent selected from the group consisting of a halogen atom and a cyano group; An alkyl group wherein at least one non-adjacent CH ₂ group of the alkyl group is substituted with any one substituent selected from the group consisting of -O-, -CO-O-, -O-CO-, and -CH = CH-; And any one alkyl group selected from the group consisting of a combination thereof

The substituted alkylaryl group for R ₈₆ is one or more non-adjacent CH ₂ groups of the alkylaryl group selected from the group consisting of -O-, -CO-O-, -O-CO-, and -CH = CH-. An alkylaryl group substituted with any one substituent)

[Formula 15]

(In Chemical Formula 15,

R ₉₁ is any one substituent selected from the group consisting of an aromatic diamine group, a diamine group substituted with a substituted or unsubstituted linear or branched alkylene group having 1 to 24 carbon atoms, and a combination thereof,

The substituted alkylene group in R ₉₁ is an alkylene group in which a hydrogen atom is substituted with any substituent selected from the group consisting of a halogen atom and a cyano group; One or more non-adjacent CH ₂ groups of the alkylene group are substituted or unsubstituted arylene groups having 2 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups having 2 to 30 carbon atoms, and substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms. Alkylene group, substituted or unsubstituted heterocycloalkylene group having 2 to 30 carbon atoms, -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'-, -NR'-, -CO -NR'-, -CH = CH-, -C≡C-, and -O-CO-O-, wherein R 'is a group consisting of a hydrogen atom and a substituted or unsubstituted C1-6 alkyl group Alkylene group substituted with any one substituent selected from the group consisting of; And any one alkylene group selected from the group consisting of a combination thereof,

R ₉₂ is any one selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 1 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. Is a substituent of, n ₉₂ is an integer of 0 to 4,

R ₉₃ and R ₉₄ each independently represent a substituent selected from a hydrogen atom, a halogen atom, a cyano group, and a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms,

The alkyl group substituted in R ₉₃ and R ₉₄ is an alkyl group in which a hydrogen atom is substituted with any substituent selected from the group consisting of a halogen atom and a cyano group; An alkyl group wherein at least one non-adjacent CH ₂ group of the alkyl group is substituted with any one substituent selected from the group consisting of -O-, -CO-O-, -O-CO-, and -CH = CH-; And a combination of any one of the alkyl groups selected from the group consisting of)

The liquid crystal photoalignment agent may include 5 to 99.9 wt% of the polysiloxane, and 0.1 to 95 wt% of the polyimide photopolymer, and 50 to 95 wt% of the polysiloxane, and the poly More preferably, it comprises 0.1 to 50% by weight of the mid photopolymer. When the content of the polysiloxane and the polyimide photopolymer is within the above range, the afterimage property improving effect is excellent and preferable.

The polysiloxane may be prepared by polymerizing the compound represented by Formulas 1 to 3 alone, or may be prepared by polymerizing two or more kinds.

As described above, when polysiloxane is prepared by polymerizing two or more kinds of the compounds represented by Formulas 1 to 3, the polysiloxane is 1 to 90 parts by weight of the compound represented by Formula 1, the compound represented by Formula 2 1 to 90 parts by weight, the compound represented by the formula (3) is preferably prepared by polymerizing at least two or more alkoxy silane compounds selected from the group consisting of 1 to 50 parts by weight.

According to another embodiment of the present invention provides a liquid crystal photoalignment film prepared using the liquid crystal photoalignment agent.

The liquid crystal photoalignment film may be prepared by applying a composition for forming a liquid crystal photoalignment film prepared by adding the liquid crystal photoalignment agent to a solvent.

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 phenol, etc. A system solvent etc. can be used preferably.

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

The poor solvent is preferably used in the range of 1 to 90% by volume with respect to the total solvent, more preferably 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, acetate 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, dietelin glycol monoethyl ether, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, ethylene glycol methyl ether acetate, ethylene glycol ethyl Ether acetate , 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 methyl butyrate, methyl 3-methoxy propionate, ethyl 3-methoxy propionate, ethyl 3-ethoxy propionate, methyl 3-ethoxy 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, and And any one selected from the group consisting of a combination of these.

The content of the solvent in the composition for forming a liquid crystal photoalignment film is not particularly determined, but the solid content of the liquid crystal photoalignment agent is 1 to 30% by weight, preferably 3 to 15% by weight, more preferably 5 to 10% by weight. Use if possible. When the content of the solid content is less than 1% by weight, there may be a problem that the uniformity of the film is lowered under the influence of the substrate surface during printing, and when the content of the solid content exceeds 30% by weight, the uniformity of the film formed during printing is reduced by the high viscosity. May be lowered and transmittance may be lowered.

The composition for forming a liquid crystal photoalignment film may include at least one epoxy compound having 2 to 4 epoxy functional groups in order to improve reliability and electro-optic properties. The epoxy compound is preferably contained in an amount of 0.01 to 50 parts by weight, more preferably 1 to 30 parts by weight based on 100 parts by weight of the liquid crystal photoalignment agent. When the content of the epoxy compound exceeds 50 parts by weight may reduce the printability or flatness when applied to the substrate, when less than 0.01 parts by weight, the effect of adding the epoxy compound is insignificant.

Specific examples of the epoxy compound include N, N, N ', N'-tetraglycidyl-4,4'-diaminodiphenylmethane (TGDDM), N, N, N', N'-tetraglycidyl -4,4'-diaminodiphenylethane, N, N, N ', N'-tetraglycidyl-4,4'-diaminodiphenylpropane, N, N, N', N'-tetragly Cydyl-4,4'-diaminodiphenylbutane, N, N, N ', N'-tetraglycidyl-4,4'-diaminobenzene, and the like, but are not limited thereto.

In addition, the composition for forming a liquid crystal photoalignment film may further use a silane coupling agent or a surfactant to improve adhesion to the substrate and to improve flatness and film coating properties.

The liquid crystal photoalignment film-forming composition may be applied to a substrate to form a liquid crystal photoalignment film. As a method of apply | coating the said liquid crystal photoalignment film formation composition to the said board | substrate, a spin coat method, the flexographic printing method, the inkjet method, etc. are mentioned. Especially, the flexographic printing method can be used suitably because it is excellent in the uniformity of the formed coating film and easy to enlarge.

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. Moreover, it is preferable to use the board | substrate with which the ITO electrode etc. for liquid crystal drive were formed from a viewpoint of the simplification of a manufacturing process.

The composition for forming a liquid crystal photoalignment film is uniformly coated on a substrate in order to increase the uniformity of the coating film, and then for 1 to 100 minutes at room temperature to 200 ° C, preferably 30 to 150 ° C, more preferably 40 to 120 ° C. It is preferable to perform temporary drying. By adjusting the volatilization degree of each component of the composition for forming a liquid crystal photoalignment film 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, preferably 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-described 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, it is preferable to completely remove the double bond included in the polyimide photopolymer by performing a uniaxial orientation treatment while reducing the exposure intensity.

According to another embodiment of the present invention, a display device including the liquid crystal photoalignment layer is provided. It is preferable that the said display device is a liquid crystal display device.

1 is a cross-sectional view of a liquid crystal display according to an exemplary embodiment of the present invention.

Referring to FIG. 1, the liquid crystal display 1 according to the exemplary embodiment of the present invention includes a lower panel 100, an upper panel 200, and a liquid crystal layer 3.

The lower panel 100 includes a gate conductor including a plurality of gate lines (not shown) and a plurality of storage electrodes 133 on an upper surface of the first substrate 110. . On the gate conductor, a gate insulating layer 140, a plurality of semiconductors 154, a plurality of pairs of ohmic contacts 163 and 165, a plurality of source electrodes 173, And a plurality of drain electrodes 175 are formed in this order.

One gate electrode 124, one source electrode 173, and one drain electrode 175 form one thin film transistor (TFT) together with the semiconductor 154.

A passivation layer 180 is formed on the exposed portion of the semiconductor 154, the source electrode 173, the drain electrode 175, and the gate insulating layer 140. A plurality of pixel electrodes 191 are formed on the passivation layer 180.

Next, the upper panel 200 will be described.

In the upper panel 200, a light blocking member 220 is formed on the second substrate 210. A plurality of color filters 230 are formed on the second substrate 210 and the light blocking member 220, and an overcoat 250 is formed on the color filters 230. The overcoat 250 may prevent the color filter 230 from being exposed to the liquid crystal layer 3, and the overcoat 250 may be omitted.

The first liquid crystal photoalignment layer 12 and the second liquid crystal photoalignment layer 22 are formed on the pixel electrode 191 of the lower panel 100 and on the common electrode 270 of the upper panel 200, respectively. The first liquid crystal photoalignment layer 12 and the second liquid crystal photoalignment layer 22 are manufactured using the liquid crystal photoalignment agent according to the embodiment of the present invention.

In FIG. 1, the liquid crystal photoalignment layers 12 and 22 are formed on both the lower panel 100 and the upper panel 200. However, the liquid crystal photoalignment layers 12 and 22 may be formed on the upper panel 200 or the upper panel. It may be formed only in any one of the lower panel 100.

The following presents specific embodiments of the present invention. However, the examples described below are merely for illustrating or explaining the present invention in detail, and the present invention is not limited thereto.

( Production Example  One: Of polysiloxane (SAA-1)  Produce)

119.5 g of ethanol was added to a four-necked flask equipped with a stirrer, a temperature controller, a nitrogen gas injector, and a cooler, and dissolved 46.7 g of oxalic acid while stirring, and heated to 60 ° C., and then maintained for 30 minutes to sufficiently dissolve oxalic acid in ethanol. It was confirmed. Thereafter, 115.6 g of the tetraethoxysilane compound represented by Formula 16 was slowly added dropwise to the oxalic acid-ethanol solution over 1 hour, and then maintained for 4 hours. The oxalic acid-ethanol solution was cooled, 120 g of N-methyl-2-pyrrolidone as an organic solvent was added thereto, and distilled to remove ethanol to obtain a polysilic acid solution having a solid content of 8% by weight, named SAA-1. It was.

[Formula 16]

Si (CH ₂ CH ₂ O) ₄

( Production Example  2: Of polysiloxane (SAA-2)  Produce)

119.5 g of ethanol was added to a four-necked flask equipped with a stirrer, a temperature controller, a nitrogen gas injector, and a cooler, and dissolved 46.7 g of oxalic acid while stirring, and heated to 60 ° C., and then maintained for 30 minutes to sufficiently dissolve oxalic acid in ethanol. It was confirmed. Thereafter, a mixture of 8.5 g of bistriethoxysilyl methane represented by the following Formula 17, 44.8 g of tetraethylorthosilicate, and 3.8 g of octadecyltrimethoxysilane was slowly added dropwise to the oxalic acid-ethanol solution over 1 hour, and then 4 Kept for hours. The oxalic acid-ethanol solution was cooled, 120 g of N-methyl-2-pyrrolidone as an organic solvent was added thereto, and distilled to remove ethanol, thereby obtaining a polysiloxane solution having a solid content of 8% by weight, named SAA-2. It was.

[Formula 17]

(CH ₂ CH ₂ O) ₃ Si-CH ₂ -Si (OCH ₂ CH ₃ ) ₃

( Production Example  3: Of polysiloxanes (SAA-3)  Produce)

A polysiloxane solution (SAA-3) was prepared in the same manner as in Preparation Example 2, except that the alkoxy silane represented by the following Formula 18 was used instead of the alkoxy silane represented by the Formula 17.

[Formula 18]

(CH ₂ CH ₂ O) ₃ Si-CH ₂ -CH ₂ -Si (OCH ₂ CH ₃ ) ₃

( Production Example  4: polyimide Of photopolymer (PSPI-1)  Produce)

Diamino benzoic acid 4- (2-ethoxycarbonyl-vinyl) -phenyl ester represented by the following formula (19) while passing nitrogen under dark conditions in a four-necked flask equipped with a stirrer, a temperature controller, a nitrogen gas injection device, and a cooler. 1.0 mole was added and N-methyl-2-pyrrolidone was added to prepare a solution.

[Formula 19]

(N = 2 in Formula 19)

1.0 mol of 1,2,3,4-cyclobutanetetracarboxylic dianhydride in the solid state was added to the solution, followed by vigorous stirring. The solid content at this time is 20% by weight, the reaction was carried out for 24 hours while maintaining the temperature at 30 ℃ to 80 ℃ 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 the catalyst and solvent were removed by vacuum distillation to obtain 20% of a solid soluble polyimide. Photopolymers were prepared.

A mixed organic solvent of N-methyl-2-pyrrolidone and γ-butyrolactone, which are organic solvents, is added to the prepared soluble polyimide photopolymer, and stirred at room temperature for 24 hours to form a soluble photo-oriented polyimide resin (PSPI- 1) was prepared.

( Production Example  5: polyimide Of photopolymer (PSPI-2)  Produce)

Photo-aligned polyimide resin (PSPI-2) was prepared in the same manner as in Preparation Example 4, except that 1.0 mole of the compound represented by the following Formula 20 was added instead of the compound represented by the above Formula 19.

[Formula 20]

( Production Example  6: polyimide Of photopolymer (PSPI-3)  Produce)

Photo-aligned polyimide resin (PSPI-3) was prepared in the same manner as in Preparation Example 4, except that 1.0 mole of the compound represented by the following Formula 21 was added instead of the compound represented by the above Formula 19.

[Formula 21]

( Production Example  7: polyimide Of photopolymer (PSPI-4)  Produce)

A photo-alignment polyimide resin (PSPI-4) was prepared in the same manner as in Preparation Example 4, except that 1.0 mol of the compound represented by the following Chemical Formula 22 was added instead of the compound represented by Chemical Formula 19.

[Formula 22]

(Liquid crystal Photoalcoholic  Produce)

( Example  One)

0.19 g of the PSPI-1 solution of 8% by weight of solids obtained in Preparation Example 4 was added to 99.9 g of the SAA-1 solution of 8% by weight of solids obtained in Preparation Example 1, stirred for 24 hours while passing nitrogen, and then particle size 0.1 Filtration was performed with a filter of µm to obtain a liquid crystal photoalignment agent (SAA-1 / PSPI-1-1) having a solid content of 8% by weight.

( Example  2)

To 50 g of the SAA-1 solution of 8% by weight of solids obtained in Preparation Example 1, 50 g of the PSPI-1 solution of 8% by weight of solids obtained in Preparation Example 4 was added, followed by stirring for 24 hours while passing nitrogen, and then having a particle diameter of 0.1 μm. It filtered by the filter and obtained the liquid crystal photoalignment agent (SAA-1 / PSPI-1-2) of 8 weight% of solid content.

( Example  3)

90 g of PSPI-1 solution of 8% by weight of solids obtained in Preparation Example 4 was added to 10 g of SAA-1 solution of 8% by weight of solids obtained in Preparation Example 1, and stirred for 24 hours while passing nitrogen. It filtered by the filter and obtained the liquid crystal photoalignment agent (SAA-1 / PSPI-1-3) of 8 weight% of solid content.

( Example  4)

0.19 g of the PSPI-1 solution of 8% by weight of solids obtained in Preparation Example 4 was added to 99.9 g of the SAA-2 solution of 8% by weight of solids obtained in Preparation Example 2, stirred for 24 hours while passing nitrogen, and then particle size 0.1 Filtration was performed with a filter of µm to obtain a liquid crystal photoalignment agent (SAA-2 / PSPI-1-1) having a solid content of 8% by weight.

( Example  5)

50 g of the 8% by weight of the PSPI-1 solution of 8% by weight of the solids obtained in Preparation Example 4 was added to 50 g of the SAA-2 solution of 8% by weight of the solids obtained in Preparation Example 2, followed by stirring for 24 hours while passing nitrogen. It filtered by the filter and obtained the liquid crystal photoalignment agent (SAA-2 / PSPI-1-2) of 8 weight% of solid content.

( Example  6)

90 g of PSPI-1 solution of 8% by weight of solids obtained in Preparation Example 4 was added to 10 g of SAA-2 solution of 8% by weight of solids obtained in Preparation Example 2.Then, the mixture was stirred for 24 hours while passing nitrogen. It filtered by the filter and obtained the liquid crystal photoalignment agent (SAA-2 / PSPI-1-3) of 8 weight% of solid content.

( Example  7)

0.19 g of the PSPI-1 solution of 8% by weight of solids obtained in Preparation Example 4 was added to 99.9 g of the SAA-3 solution of 8% by weight of solids obtained in Preparation Example 3, stirred for 24 hours while passing nitrogen, and then the particle size was 0.1 Filtration was performed with a filter of µm to obtain a liquid crystal photoalignment agent (SAA-3 / PSPI-1-1) having a solid content of 8% by weight.

( Example  8)

50 g of the 8% by weight of the PSPI-1 solution of 8% by weight of the solids obtained in Preparation Example 4 was added to 50 g of the SAA-3 solution of 8% by weight of the solids obtained in Preparation Example 3, followed by stirring for 24 hours while passing nitrogen, and then a particle diameter of 0.1 μm. Filtration was carried out with a filter of to obtain a liquid crystal photoalignment agent (SAA-3 / PSPI-1-2) having a solid content of 8% by weight.

( Example  9)

90 g of the PSPI-1 solution having 8% by weight of the solid content obtained in Preparation Example 4 was added to 10 g of the SAA-3 solution having 8% by weight of the solid content obtained in Preparation Example 3, followed by stirring for 24 hours while passing nitrogen. It filtered by the filter and obtained the liquid crystal photoalignment agent (SAA-3 / PSPI-1-3) of 8 weight% of solid content.

( Example  10)

0.19 g of the PSPI-2 solution of 8% by weight of solids, obtained in Preparation Example 5, was added to 99.9 g of the SAA-2 solution of 8% by weight of solids obtained in Preparation Example 2, and stirred for 24 hours while passing nitrogen. Filtration was carried out with a filter of µm to obtain a liquid crystal photoalignment agent (SAA-2 / PSPI-2-1) having a solid content of 8% by weight.

( Example  11)

To 50 g of the SAA-2 solution of 8% by weight of solids obtained in Preparation Example 2, 50 g of the PSPI-2 solution of 8% by weight of solids obtained in Preparation Example 5 was added, followed by stirring for 24 hours while passing nitrogen. It filtered by the filter and obtained the liquid crystal photoalignment agent (SAA-2 / PSPI-2-2) of 8 weight% of solid content.

( Example  12)

After adding 90 g of PSPI-2 solution of 8% by weight of solids obtained in Preparation Example 5 to 10 g of SAA-2 solution of 8% by weight of solids obtained in Preparation Example 2, stirring for 24 hours while passing nitrogen, It filtered by the filter and obtained the liquid crystal photoalignment agent (SAA-2 / PSPI-2-3) of 8 weight% of solid content.

( Example  13)

0.19 g of the PSPI-3 solution of 8% by weight of solids, obtained in Preparation Example 6, was added to 99.9 g of the SAA-2 solution of 8% by weight of solids obtained in Preparation Example 2, followed by stirring for 24 hours while passing nitrogen. Filtration was carried out with a filter of µm to obtain a liquid crystal photoalignment agent (SAA-2 / PSPI-3-1) having a solid content of 8% by weight.

( Example  14)

To 50 g of the SAA-2 solution of 8% by weight of solids obtained in Preparation Example 2, 50 g of the PSPI-3 solution of 8% by weight of solids obtained in Preparation Example 6 was added thereto, followed by stirring for 24 hours while passing nitrogen. It filtered by the filter and obtained the liquid crystal photoalignment agent (SAA-2 / PSPI-3-2) of 8 weight% of solid content.

( Example  15)

90 g of the PSPI-3 solution of 8% by weight of the solid content obtained in Preparation Example 6 was added to 10 g of the SAA-2 solution of 8% by weight of the solid content obtained in Preparation Example 2, followed by stirring for 24 hours while passing nitrogen, and having a particle diameter of 0.1 μm. It filtered by the filter and obtained the liquid crystal photoalignment agent (SAA-2 / PSPI-3-3) of 8 weight% of solid content.

( Example  16)

0.19 g of the PSPI-4 solution of 8% by weight of solids obtained in Preparation Example 7 was added to 99.9 g of the SAA-2 solution of 8% by weight of solids obtained in Preparation Example 2.Then, the mixture was stirred for 24 hours while passing nitrogen, and then the particle size was 0.1 Filtration was carried out with a filter of μm to obtain a liquid crystal photoalignment agent (SAA-2 / PSPI-4-1) having a solid content of 8% by weight.

( Example  17)

To 50 g of the SAA-2 solution of 8% by weight of solids obtained in Preparation Example 2, 50 g of the PSPI-4 solution of 8% by weight of solids obtained in Preparation Example 7 was added, followed by stirring for 24 hours while passing nitrogen. It filtered by the filter and obtained the liquid crystal photoalignment agent (SAA-2 / PSPI-4-2) of 8 weight% of solid content.

( Example  18)

90 g of the PSPI-4 solution of 8% by weight of solids obtained in Preparation Example 7 was added to 10 g of the SAA-2 solution of 8% by weight of solids obtained in Preparation Example 2, followed by stirring for 24 hours while passing nitrogen, and then a particle diameter of 0.1 μm. Filtration was carried out with the filter of the liquid crystal photoalignment agent (SAA-2 / PSPI-4-3) of 8 weight% of solid content.

( Comparative example  One)

The photo-alignment solution (PSPI-1) of 8 weight% of solid content obtained by the manufacture example 4 was filtered through the filter of 0.1 micrometer, and the liquid crystal photoalignment agent of 8 weight% of solid content was obtained.

( Comparative example  2)

The photo-alignment solution (PSPI-2) of 8 weight% of solid content obtained by the manufacture example 5 was filtered through the filter of 0.1 micrometer, and the liquid crystal photoalignment agent of 8 weight% of solid content was obtained.

( Comparative example  3)

The photo-alignment solution (PSPI-3) of 8 weight% of solid content obtained by the manufacture example 6 was filtered through the filter of 0.1 micrometer, and the liquid crystal photoalignment agent of 8 weight% of solid content was obtained.

( Comparative example  4)

The photo-alignment solution (PSPI-4) of 8 weight% of solid content obtained by the manufacture example 7 was filtered through the filter of 0.1 micrometer, and the liquid crystal photoalignment agent of 8 weight% of solid content was obtained.

(Printability measurement)

The liquid crystal photo-alignment agents prepared in Examples 1 to 18 and Comparative Examples 1 to 4 were applied onto an ITO substrate having a size of 10 cm × 10 cm, spin-coated to be uniformly 0.1 μm thick, and then placed on a hot plate. The liquid crystal photoalignment film was manufactured by going through a desolvent process at a temperature of 70 ° C. and a curing process at a temperature of 210 ° C.

The printability of the liquid crystal photoalignment agent was evaluated by observing the spreading and curling characteristics of the prepared liquid crystal photoalignment agent through the naked eye and an optical microscope. The printability evaluation results are shown in Table 1 below.

(Liquid crystal Orientation  Measure)

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 18 and Comparative Examples 1 to 4 was applied to the patterned ITO substrate, spin-coated to a thickness of 0.1 μm, and then subjected to curing at 70 ° C. and 210 ° C.

The two ITO substrates subjected to the curing process using an exposure machine (Ushio LPUV, UIS-S2021J7-YD01) under a certain angle and a constant energy are exposed in opposite directions (90 degrees for VA mode). After that, the 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.

( Pretilt  Measure)

The liquid crystal cell for pretilt angle evaluation was manufactured separately from the above method so as to maintain the cell gap at 50 μm.

In order to measure the pretilt angles of the liquid crystal photo-alignment agents prepared in Examples 1 to 18 and Comparative Examples 1 to 4, a liquid crystal cell having a 50 μm cell gap was prepared and a crystal rotation method was used. The pretilt angle measurement results are shown in Table 1 below.

(Measurement of electrical and optical characteristics)

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

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

The voltage-transmittance curve is one of the important electrical and optical characteristics that determine the driving voltage of the liquid crystal display device. It is a curve normalized to 0% of dark light.

The voltage holding ratio refers to the degree to which the liquid crystal layer in the state of floating with the external power source is charged 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 from the ionized liquid crystal layer to the alignment layer. 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 results of the electrical and optical properties of the liquid crystal photoalignment agent using the liquid crystal cell are shown in Table 2 below.

TABLE 1

sample Printability Vertical orientation Optical orientation Pretilt angle (°) Example 1 Good Good Good 89.96 Example 2 Good Good Good 89.97 Example 3 Good Good Good 89.98 Example 4 Good Good Good 89.99 Example 5 Good Good Good 89.97 Example 6 Good Good Good 89.94 Example 7 Good Good Good 89.99 Example 8 Good Good Good 89.98 Example 9 Good Good Good 89.96 Example 10 Good Good Good 89.96 Example 11 Good Good Good 89.96 Example 12 Good Good Good 89.94 Example 13 Good Good Good 89.96 Example 14 Good Good Good 89.94 Example 15 Good Good Good 89.93 Example 16 Good Good Good 89.96 Example 17 Good Good Good 89.94 Example 18 Good Good Good 89.92 Comparative Example 1 Good Good Good 89.89 Comparative Example 2 Good Good Good 89.89 Comparative Example 3 Good Good Good 89.89 Comparative Example 4 Good Good Good 89.90

TABLE 2

sample Voltage-Transmittance Voltage retention rate (%) Residual DC (by C-V) Room temperature (25 ℃) High temperature (60 ℃) Example 1 Good 99.22 99.18 62 Example 2 Good 99.21 99.13 60 Example 3 Good 99.9 99.12 62 Example 4 Good 99.26 99.11 56 Example 5 Good 99.33 99.18 62 Example 6 Good 99.36 99.20 66 Example 7 Good 99.19 99.08 65 Example 8 Good 99.26 99.15 68 Example 9 Good 99.28 99.16 72 Example 10 Good 99.26 99.10 71 Example 11 Good 99.29 99.16 68 Example 12 Good 99.31 99.16 79 Example 13 Good 99.18 99.05 80 Example 14 Good 99.18 99.08 88 Example 15 Good 99.22 99.10 87 Example 16 Good 99.19 99.05 105 Example 17 Good 99.13 99.08 103 Example 18 Good 99.24 99.05 112 Comparative Example 1 Good 98.51 97.21 348 Comparative Example 2 Good 98.11 96.75 401 Comparative Example 3 Good 97.85 96.05 680 Comparative Example 4 Good 97.76 96.01 765

Referring to Table 1, it can be seen that the liquid crystal photoalignment agent prepared in Examples 1 to 18 can be used as a liquid crystal photoalignment film because of good printability, vertical alignment, photoalignment, and pretilt angle.

Referring to Table 2, it can be seen that the liquid crystal photo-alignment agent prepared in Examples 1 to 18 had a good voltage-transmittance and a voltage holding ratio of 99% or more. On the other hand, the liquid crystal photo-alignment agent prepared in Comparative Examples 1 to 4 can be seen that the voltage retention is less than 99%.

In addition, it can be seen that the liquid crystal photo-alignment agent prepared in Examples 1 to 18 has a low residual DC, whereas the liquid crystal photo-alignment agent prepared in Comparative Examples 1 to 4 has a very high residual DC.

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 18 is superior to the afterimage property than the liquid crystal photoalignment agent prepared in Comparative Examples 1 to 4.

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. Therefore, it should be understood that the embodiments described above are exemplary in all respects and not restrictive.

1 is a cross-sectional view of a liquid crystal display according to an exemplary embodiment of the present invention.

<Explanation of symbols for the main parts of the drawings>

1: liquid crystal display device 3: liquid crystal layer

12: first liquid crystal photoalignment film 22: second liquid crystal photoalignment film

100: lower display panel 110: first substrate

175: drain electrode 191: pixel electrode

200: upper display panel 210: second substrate

230: color filter 270: common electrode

Claims (13)

A polysiloxane polymer prepared by polymerizing any one alkoxy silane compound selected from the group consisting of a compound represented by the following Chemical Formulas 1 to 3, and a combination thereof, and Polyimide photopolymer represented by the following formula (4) Liquid crystal photo-alignment agent comprising a. [Formula 1] Si (R ₁ ) ₄ (In Formula 1, The four R ₁ are each independently a substituent selected from the group consisting of hydroxy, alkoxy having 1 to 5 carbon atoms, and an aryloxy group having 6 to 20 carbon atoms) [Formula 2] Si (R ₂ ) ₄ (In Formula 2, Each of the four R ₂ is independently a hydrogen atom, an alkyl group or fluoroalkyl group having 1 to 20 carbon atoms, an aryl group or fluoroaryl group having 6 to 20 carbon atoms, hydroxy, alkoxy having 1 to 5 carbon atoms, and 6 to 20 carbon atoms Any substituent selected from the group consisting of an aryloxy group, One or _two of the four R ₂ are each independently selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 20 carbon atoms or a fluoroalkyl group, an aryl group having 6 to 20 carbon atoms or a fluoraryl group, and 2 or 3 are hydroxy Oxy, alkoxy having 1 to 5 carbon atoms, and an aryloxy group having 6 to 20 carbon atoms). [Formula 3] (R ₄ ) ₃ Si- (R ₃ ) _n -Si (R ₄ ) ₃ (In Chemical Formula 3, R ₃ is any one selected from the group consisting of an alkylene group or a fluoroalkylene group having 1 to 8 carbon atoms, an arylene group or a fluorarylene group having 6 to 20 carbon atoms, and n is an integer of 0 to 8, Each of the six R _{4 's} is independently a substituent selected from the group consisting of hydroxy, alkoxy having 1 to 5 carbon atoms, and aryloxy group having 6 to 20 carbon atoms) [Formula 4]

(In Formula 4, R ₅ is a tetravalent organic group derived from any one acid dianhydride selected from the group consisting of aliphatic cyclic dianhydrides and aromatic acid dianhydrides, R ₆ is a divalent organic group derived from any one photodiamine selected from the group consisting of coumarin-based photodiamine, chalcone-based photodiamine, and cinnamate-based photodiamine. The substituted Iran hydrogen atom is a halogen group, an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, 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 Means substituted with any one of substituents selected from the group consisting of a combination of these) The method of claim 1, The aliphatic cyclic acid dianhydride includes 1,2,3,4-cyclobutanetetracarboxylic dianhydride (CBDA), 5- (2,5-dioxotetrahydrofuryl) -3-methylcyclohexene-1,2- Dicarboxylic 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 dianhydride And liquid crystal photo-alignment agent which is any one selected from the group consisting of these. The method of claim 1, The R ₅ is a liquid crystal photo-alignment agent which is a tetravalent organic group selected from the group consisting of a compound represented by the following formulas 5 to 9, and combinations thereof. [Formula 5] [Formula 6] [Formula 7]

[Formula 8] [Formula 9]

(In Chemical Formulas 5 to 9, R ₁₀ is any one selected from the group consisting of a substituted or unsubstituted C1-20 alkyl group, a substituted or unsubstituted C1-30 aryl group, and a substituted or unsubstituted C2-30 heteroaryl group and the substituent group, and wherein n ₁₀ is an integer of 0 to 3, R ₁₁ to R ₁₇ are each independently a hydrogen atom, a substituted or unsubstituted C1-20 alkyl group, a substituted or unsubstituted C1-30 aryl group, and a substituted or unsubstituted C2-30 hetero Any substituent selected from the group consisting of an aryl group, The substituted Iran hydrogen atom is a halogen group, an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, 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 Means substituted with any one of substituents selected from the group consisting of a combination of these) The method of claim 1, The aromatic acid dianhydride is pyromellitic dianhydride (PMDA), non-phthalic dianhydride (BPDA), oxydiphthalic dianhydride (ODPA), benzophenone tetracarboxylic dianhydride (BTDA), hexafluoroisopropylidene diphthalic dianhydride (6-FDA), and a liquid crystal photo-alignment agent which is any one selected from the group consisting of these. The method of claim 1, R ₅ is a liquid crystal photo-alignment agent of any one selected from the group consisting of a compound represented by Formula 10, a compound represented by Formula 11, and a combination thereof. [Formula 10] [Formula 11]

(In Chemical Formula 10, and Formula 11, R ₂₁ and R ₂₂ are each independently a hydrogen atom, a substituted or unsubstituted C1-20 alkyl group, a substituted or unsubstituted C1-30 aryl group, and a substituted or unsubstituted C2-30 hetero Any substituent selected from the group consisting of an aryl group, R ₂₄ and R ₂₅ are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 1 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. One substituent selected from the group consisting of, wherein n ₂₄ , and n ₂₅ are each independently an integer of 0 to 3, R ₂₃ is O, CO, substituted or unsubstituted C 1-6 alkylene group, substituted or unsubstituted C 3 -C 30 cycloalkylene group, and substituted or unsubstituted C 2 -C 30 heterocycloalkylene Any one selected from the group consisting of groups, n ₂₃ is an integer of 0 or 1, The substituted Iran hydrogen atom is a halogen group, an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, 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 Means substituted with any one of substituents selected from the group consisting of a combination of these) The method of claim 1, The cinnamate photodiamine is any one selected from the group consisting of a compound represented by the following formula (12), a compound represented by the following formula (13), and a combination thereof. [Formula 12]

(In Chemical Formula 12, R ₇₁ is selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms Which is any substituent, R ₇₂ is any one selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. and the substituent group, and wherein n ₇₂ is an integer of 0 to 3, The substituted Iran hydrogen atom is a halogen group, an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, 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 Means substituted with any one of substituents selected from the group consisting of a combination of these) [Formula 13]

(In Chemical Formula 13, R ₇₇ is any one substituent selected from the group consisting of an aromatic diamine group, a diamine group including a substituted or unsubstituted linear or branched alkylene group having 1 to 24 carbon atoms, and a combination thereof, The substituted alkylene group in R ₇₇ is an alkylene group in which a hydrogen atom is substituted with any substituent selected from the group consisting of a halogen atom and a cyano group; One or more non-adjacent CH ₂ groups of the alkylene group are substituted or unsubstituted arylene groups having 2 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups having 2 to 30 carbon atoms, and substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms. Alkylene group, substituted or unsubstituted heterocycloalkylene group having 2 to 30 carbon atoms, -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'-, -NR'-, -CO -NR'-, -CH = CH-, -C≡C-, and -O-CO-O-, wherein R 'is a group consisting of a hydrogen atom and a substituted or unsubstituted C1-6 alkyl group Alkylene group substituted with any one substituent selected from the group consisting of; And any one alkylene group selected from the group consisting of a combination thereof, R ₇₄ is any one selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 1 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. One substituent, n ₇₄ is an integer of 0 to 4, R ₇₅ and R ₇₆ are each independently a substituent selected from a hydrogen atom, a halogen atom, a cyano group, and a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, The alkyl group substituted in R ₇₅ and R ₇₆ is an alkyl group wherein a hydrogen atom is substituted with any substituent selected from the group consisting of a hetero atom and a cyano group; An alkyl group wherein at least one non-adjacent CH ₂ group of the alkyl group is substituted with any one substituent selected from the group consisting of -O-, -CO-O-, -O-CO-, and -CH = CH-; And any one alkyl group selected from the group consisting of a combination thereof, R ₇₃ is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylaryl group having 7 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted Selected pyrimidinyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted thiophenyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted naphthyl group, and substituted or unsubstituted phenyl group. Which is any substituent, The alkyl group substituted in R ₇₃ is an alkyl group in which a hydrogen atom is substituted with any substituent selected from the group consisting of halogen and cyano group; An alkyl group wherein at least one non-adjacent CH ₂ group of the alkyl group is substituted with any one substituent selected from the group consisting of -O-, -CO-O-, -O-CO-, and -CH = CH-; And any one alkyl group selected from the group consisting of a combination thereof, The substituted alkylaryl group for R _{73 is selected} from the group consisting of -O-, -CO-O-, -O-CO-, and -CH = CH-, in which at least one non-adjacent CH ₂ group of the alkylaryl group is selected. An alkylaryl group substituted with any one substituent, The substituted Iran hydrogen atom is a halogen group, an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, 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 Means substituted with any one of substituents selected from the group consisting of a combination of these) The method of claim 1, The chalcone-based photodiamine is a liquid crystal photo-alignment agent is a compound represented by the following formula (14). [Formula 14]

(In Formula 14, R ₈₁ is any substituent selected from the group consisting of an aromatic diamine group, a diamine group substituted with a substituted or unsubstituted linear or branched alkylene group having 1 to 24 carbon atoms, and a combination thereof, The alkylene substituted at R ₈₁ is an alkylene group in which a hydrogen atom is substituted with any substituent selected from the group consisting of a halogen atom and a cyano group; One or more non-adjacent CH ₂ groups of the alkylene group are substituted or unsubstituted arylene groups having 2 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups having 2 to 30 carbon atoms, and substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms. Alkylene group, substituted or unsubstituted heterocycloalkylene group having 2 to 30 carbon atoms, -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'-, -NR'-, -CO —NR′—, —CH═CH—, —C≡C—, and —O—CO—O—, wherein R ′ is a hydrogen atom and a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms An alkylene group substituted with any substituent selected from the group consisting of; And any one alkylene group selected from the group consisting of a combination thereof, R ₈₂ and R ₈₅ are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 1 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. One substituent selected from the group consisting of, n ₈₂ , and n ₈₅ are each independently an integer of 0 to 4, R ₈₃ and R ₈₄ are each independently any substituent selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, and a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, The alkyl group substituted in R ₈₃ and R ₈₄ is an alkyl group wherein a hydrogen atom is substituted with any substituent selected from the group consisting of a halogen atom and a cyano group; An alkyl group wherein at least one non-adjacent CH ₂ group of the alkyl group is substituted with any one substituent selected from the group consisting of -O-, -CO-O-, -O-CO-, and -CH = CH-; And any one alkyl group selected from the group consisting of a combination thereof, R ₈₆ is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylaryl group having 7 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted Substituted pyrimidinyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted thiophenyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted naphthyl group, and substituted or unsubstituted phenyl group. Any one substituent is selected, The alkyl group substituted in R ₈₆ is an alkyl group in which a hydrogen atom is substituted with any substituent selected from the group consisting of a halogen atom and a cyano group; An alkyl group wherein at least one non-adjacent CH ₂ group of the alkyl group is substituted with any one substituent selected from the group consisting of -O-, -CO-O-, -O-CO-, and -CH = CH-; And any one alkyl group selected from the group consisting of a combination thereof. The substituted alkylaryl group for R ₈₆ is one or more non-adjacent CH ₂ groups of the alkylaryl group selected from the group consisting of -O-, -CO-O-, -O-CO-, and -CH = CH-. An alkylaryl group substituted with any one substituent, The substituted Iran hydrogen atom is a halogen group, an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, 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 Means substituted with any one of substituents selected from the group consisting of a combination of these) The method of claim 1, The coumarin-based photodiamine is a liquid crystal photo-alignment agent that is a compound represented by the formula (15). [Formula 15]

(In Chemical Formula 15, R ₉₁ is any one substituent selected from the group consisting of an aromatic diamine group, a diamine group substituted with a substituted or unsubstituted linear or branched alkylene group having 1 to 24 carbon atoms, and a combination thereof, The substituted alkylene group in R ₉₁ is an alkylene group in which a hydrogen atom is substituted with any substituent selected from the group consisting of a halogen atom and a cyano group; One or more non-adjacent CH ₂ groups of the alkylene group are substituted or unsubstituted arylene groups having 2 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups having 2 to 30 carbon atoms, and substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms. Alkylene group, substituted or unsubstituted heterocycloalkylene group having 2 to 30 carbon atoms, -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'-, -NR'-, -CO —NR′—, —CH═CH—, —C≡C—, and —O—CO—O—, wherein R ′ is a hydrogen atom and a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms An alkylene group substituted with any substituent selected from the group consisting of; And any one alkylene group selected from the group consisting of a combination thereof, R ₉₂ is any one selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 1 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. Is a substituent of, n ₉₂ is an integer of 0 to 4, R ₉₃ and R ₉₄ each independently represent a substituent selected from a hydrogen atom, a halogen atom, a cyano group, and a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, The alkyl group substituted in R ₉₃ and R ₉₄ is an alkyl group in which a hydrogen atom is substituted with any substituent selected from the group consisting of a halogen atom and a cyano group; An alkyl group wherein at least one non-adjacent CH ₂ group of the alkyl group is substituted with any one substituent selected from the group consisting of -O-, -CO-O-, -O-CO-, and -CH = CH-; And any one alkyl group selected from the group consisting of a combination thereof, The substituted Iran hydrogen atom is a halogen group, an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, 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 Means substituted with any one of substituents selected from the group consisting of a combination of these) The method of claim 1, The liquid crystal photo-alignment agent is a liquid crystal photo-alignment agent containing 10 to 99.9% by weight of the polysiloxane polymer, and 0.1 to 90% by weight of the polyimide photopolymer based on the total solid. The method of claim 1, The polysiloxane is at least two selected from the group consisting of 1 to 90 parts by weight of the compound represented by Formula 1, 1 to 90 parts by weight of the compound represented by Formula 2, and 1 to 50 parts by weight of the compound represented by Formula 3 The liquid crystal photoalignment agent manufactured by superposing | polymerizing the above alkoxy silane compound. The method of claim 1, The liquid crystal photoalignment agent is a solid content of 1 to 30% by weight. A liquid crystal photoalignment film prepared by applying the liquid crystal photoalignment agent according to any one of claims 1 to 11 to a substrate. A liquid crystal display comprising the liquid crystal photoalignment film according to claim 12.

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