KR20160068869A - Composition, liquid crystal alignment agent, liquid crystal alignment film, and liquid crystal display element - Google Patents

Abstract

(식 [1] 중, X¹ 및 X² 는 각각 독립적으로, 탄소수 1 ∼ 3 의 알킬기를 나타내고, X³ 및 X⁴ 는 각각 독립적으로, 탄소수 1 ∼ 3 의 알킬기를 나타낸다) 로 나타내는 용매 ; 그리고 (B) 성분 : 폴리실록산을 함유하는 조성물을 제공한다.The present invention relates to (A) component:

(In the formula [1], X ¹ and X ² each independently represent an alkyl group having 1 to 3 carbon atoms, and X ³ and X ⁴ each independently represent an alkyl group having 1 to 3 carbon atoms); And component (B): polysiloxane.

Description

TECHNICAL FIELD [0001] The present invention relates to a composition, a liquid crystal alignment treatment agent, a liquid crystal alignment film and a liquid crystal display element,

The present invention relates to a composition used for forming a resin film, a liquid crystal alignment treatment agent used in the production of a liquid crystal display element, a liquid crystal alignment film obtained from the liquid crystal alignment treatment agent, and a liquid crystal display element using the liquid crystal alignment film.

The resin film made of an organic material such as a polymer material is widely used as an interlayer insulating film or a protective film in an electronic device, with attention being paid to ease of formation and insulation performance. Among them, in a liquid crystal display element well known as a display device, a resin film made of an organic material or an inorganic material is used as a liquid crystal alignment film.

At present, as a composition for forming a resin film used industrially, a composition comprising a polyimide polymer having excellent durability and a polysiloxane polymer obtained by polycondensation of an alkoxysilane is used.

In recent years, an inorganic resin film formed from a composition containing a polysiloxane polymer is used for an interlayer insulating film, a protective film, and a liquid crystal alignment film. In particular, it is an object of the present invention to provide a liquid crystal display device capable of improving the alignment of liquid crystal with respect to heat (for example, Patent Document 1), improving the film hardness of the liquid crystal alignment film and improving the printability of the liquid crystal alignment treatment agent (For example, Patent Document 2), a liquid crystal alignment treatment agent using a polysiloxane-based polymer and a liquid crystal alignment film have been proposed.

Japanese Patent Application Laid-Open No. 2001-27761 International Publication No. 2008/044644

The resin film obtained from the polysiloxane-based polymer is widely used as an interlayer insulating film or a protective film in an electronic device, and further, a liquid crystal alignment film of a liquid crystal display element. In these respects, it is required to increase the film properties of the resin coating film, the protective film, and the liquid crystal alignment film. In other words, the improvement of the film properties of these films is effective for suppressing defects in electronic devices and liquid crystal display elements that are caused by defective coating properties.

2. Description of the Related Art In recent years, liquid crystal display devices have been widely put to practical use in mobile applications (such as digital cameras and cellular phones) of a liquid crystal television or a fixed screen of a large screen. Along with this, unevenness of the substrate size and the step of the substrate used in comparison with the conventional one is increasing. Also in such a situation, it is required that a liquid crystal alignment film is uniformly applied to a large substrate or step from the viewpoints of improvement of display characteristics of liquid crystal display elements and suppression of defects. Particularly, with respect to the unevenness of the substrate step difference, it is required that the liquid crystal alignment film is coated with a uniform film thickness (also referred to as stepwise followability).

Since the composition obtained from the polysiloxane-based polymer and the liquid crystal alignment treatment agent have a low molecular weight of the polysiloxane-based polymer, the step traceability of the resin film and the liquid crystal alignment film (collectively referred to as resin film) is lowered. That is, a resin film having a uniform film thickness can not be obtained with respect to the unevenness of the substrate step difference. Specifically, the resin film is not coated on the convex portion of the stepped portion of the substrate, or the film thickness thereof tends to become thin. As a result, the function as an interlayer insulating film and a protective film in an electronic device and further as a liquid crystal alignment film of a liquid crystal display element can not be developed, and these defects are liable to occur.

The liquid crystal alignment film is also used to control the angle of the liquid crystal with respect to the substrate, that is, the control of the pretilt angle of the liquid crystal. Particularly, in the VA (Vertical Alignment) mode and the PSA (Polymer sustained alignment) mode, it is necessary to orient the liquid crystal vertically. Therefore, the liquid crystal alignment film is required to have a capability of vertically aligning the liquid crystal ) Is required. In addition, not only a high vertical alignment property but also a stability thereof are becoming important in a liquid crystal alignment film. Particularly, in a liquid crystal display device using a backlight having a large amount of heat for obtaining a high brightness and having a large amount of light irradiation, for example, in a car navigation system or a large television, it is used or left in an environment exposed to high temperature and light for a long time . Under such severe conditions, when the vertical alignment property is lowered, problems such as failure to obtain initial display characteristics or occurrence of display irregularities occur.

Therefore, the present invention aims to provide a composition having the above characteristics. That is, an object of the present invention is to provide a composition capable of suppressing occurrence of pinholes accompanied by cratering when forming a resin film, and further having a step-wise followability to the unevenness of the stepped substrate.

In addition, in the liquid crystal alignment treatment agent using the composition of the present invention, it is possible to suppress the occurrence of pinholes accompanying cratering when forming the liquid crystal alignment film, and further to provide a liquid crystal alignment treatment agent . It is another object of the present invention to provide a liquid crystal alignment treatment agent which becomes a liquid crystal alignment film capable of exhibiting a stable pretilt angle even after exposure to high temperature and light irradiation for a long time.

In addition, the present invention is to provide a resin coating obtained from the above composition, a liquid crystal alignment film obtained from the above liquid crystal alignment treatment agent, and a liquid crystal display element having the above liquid crystal alignment film.

As a result of intensive studies, the inventors of the present invention have found out that a composition containing a polysiloxane obtained by polycondensing a solvent having a specific structure and an alkoxysilane having a specific structure is very effective for achieving the above object, It came to the following.

That is, the present invention has the following points.

(1) Component (A): The following formula [1]:

[Chemical Formula 1]

(Wherein X ¹ and X ² each independently represent an alkyl group having 1 to 3 carbon atoms, and X ³ and X ⁴ each independently represent an alkyl group having 1 to 3 carbon atoms); And

Component (B): The following formulas [2a], [2b] and [2c]

(2)

Wherein A ¹ is a group represented by the following formulas [2a-1] and [2a-2]:

(3)

(Wherein, Y ¹ represents a single _{bond, - (CH 2) a -} (a is an integer of 1 ~ 15), -O-, -CH 2 O-, -CONH-, -NHCO-, -CON (CH _{3) -, -N (CH 3} ) it represents at least one coupler is selected from CO-, -COO- and -OCO-, Y ² is a single bond or _{- (CH 2) b - (} b is 1 to 15 represents a an integer), Y ³ represents a single _{bond, - (CH 2) c -} (c is an integer of 1 ~ 15), -O-, -CH 2 O-, -COO- and -OCO- selected from Y ⁴ represents at least one kind of cyclic group selected from a benzene ring, a cyclohexane ring and a heterocyclic ring, or a divalent organic group having a steroid skeleton and having from 17 to 51 carbon atoms, and the cyclic group ^May be substituted with an alkyl group having 1 to 3 carbon atoms, an alkoxyl group having 1 to 3 carbon atoms, a fluorine-containing alkyl group having 1 to 3 carbon atoms, a fluoro-containing alkoxyl group having 1 to 3 carbon atoms, or a fluorine atom, Benzene ring, cyclohexyl An alkyl group having 1 to 3 carbon atoms, an alkoxyl group having 1 to 3 carbon atoms, a fluorine-containing alkyl group having 1 to 3 carbon atoms, a fluorine-containing alkyl group having 1 to 3 carbon atoms, N is an integer of 0 to 4, Y ⁶ is an alkyl group having 1 to 22 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, a fluorine atom having 1 to 22 carbon atoms, a fluorine-containing alkoxyl group having 1 to 3 carbon atoms, Containing alkyl group, an alkoxyl group having 1 to 22 carbon atoms, and a fluorinated alkoxyl group having 1 to 22 carbon atoms) and

[Chemical Formula 4]

(Wherein Y ⁷ represents a single bond, -O-, -CH ₂ O-, -CONH-, -NHCO-, -CON (CH ₃ ) -, -N (CH ₃ ) CO-, OCO- and Y ⁸ represents an alkyl group having from 8 to 22 carbon atoms or a fluorine-containing alkyl group having from 6 to 18 carbon atoms), and A < ² > represents at least one structure selected from the group consisting of Each independently represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, A ³ each independently represents an alkyl group having 1 to 5 carbon atoms, m ¹ represents an integer of 1 or 2, and n ¹ represents 0 to 2 And p ¹ represents an integer of 0 to 3, provided that m ¹ + n ¹ + p ¹ is an integer of 4};

[Chemical Formula 5]

Wherein B ¹ each independently represents a group having 2 to 12 carbon atoms having at least one kind selected from a vinyl group, an epoxy group, an amino group, a mercapto group, an isocyanate group, a methacryl group, an acrylic group, an ureido group and a cinnamoyl group B ² each independently represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms; B ³ independently represents an alkyl group having 1 to 5 carbon atoms or an alkoxyalkyl group having 1 to 5 carbon atoms; and m ² Represents an integer of 1 or 2, n ² represents an integer of 0 to 2, and p ² represents an integer of 0 to 3, provided that m ² + n ² + p ² represents an integer of 4); And

[Chemical Formula 6]

(Wherein D ¹ each independently represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, D ² each independently represents an alkyl group having 1 to 5 carbon atoms, and n ³ represents an integer of 0 to 3)

And an alkoxysilane represented by the following general formula

≪ / RTI >

(2) When the solvent of the component (A) is a compound represented by the following formula [1a]:

(7)

(1). ≪ / RTI >

(3) the alkoxysilane represented by the formula [2b] of the component (B) is at least one selected from the group consisting of allyltriethoxysilane, allyltrimethoxysilane, diethoxymethylvinylsilane, dimethoxymethylvinylsilane, triethoxvinylsilane, vinyl 3- (trimethoxysilyl) propyl methacrylate, 3- (trimethoxysilyl) propyl acrylate and 3- (trimethoxysilyl) propyl methacrylate, The composition according to the above (1) or (2), wherein the composition is at least one alkoxysilane selected from propyl methacrylate.

(4) The positive resist composition as described in the above item (1), wherein the alkoxysilane represented by the formula [2b] of the component (B) is at least one compound selected from the group consisting of 3-glycidyloxypropyl (dimethoxy) methylsilane, 3-glycidyloxypropyl (diethoxy) The composition according to (1) or (2) above, wherein the alkoxysilane is at least one alkoxysilane selected from the group consisting of silyloxypropyltrimethoxysilane and 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane.

(5) The polysiloxane of the above component (B) is obtained by polycondensing a polysiloxane obtained by polycondensation of an alkoxysilane represented by the formula [2a] and a formula [2b], or an alkoxysilane represented by the formula [2a] (1) to (4), wherein the polysiloxane is a polysiloxane containing any one of the polysiloxanes obtained.

(6) Any one of the above-mentioned (1) to (5), wherein the polysiloxane of the component (B) is a polysiloxane obtained by polycondensing the alkoxysilane represented by the formula [2a], the formula [2b] ≪ / RTI >

(7) The composition according to any one of (1) to (7), wherein the composition contains at least one compound selected from the group consisting of methyl ethyl ketone, cyclohexanone, cyclopentanone, 4-hydroxy- Butanediol, 2,3-butanediol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene At least 1 selected from glycol monobutyl ether, ethylene glycol monopropyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, dipropylene glycol monomethyl ether, dipropylene glycol dimethyl ether and furfuryl alcohol. The composition according to any one of (1) to (6), wherein the composition contains a solvent of a species.

(8) A process for producing a composition, which comprises adding to a composition at least one solvent selected from the group consisting of N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone,? -Butyrolactone and 1,3- (1) to (7) above.

(9) A crosslinkable compound having at least one substituent selected from the group consisting of a hydroxyl group, a hydroxyalkyl group and a lower alkoxyalkyl group in the composition, a crosslinkable compound having an epoxy group, an isocyanate group, an oxetane group or a cyclocarbonate group, , And at least one crosslinkable compound selected from a crosslinkable compound having a polymerizable unsaturated bond. The composition according to any one of (1) to (8) above,

(10) The composition according to any one of (1) to (9) above, wherein the component (A) is 20 to 80 mass% of the total solvent contained in the composition.

(11) The composition according to any one of (1) to (10) above, wherein the component (B) is 0.1% by mass to 30% by mass in the composition.

(12) A resin film obtained from the composition according to any one of (1) to (11).

(13) A liquid crystal alignment treatment agent obtained from the composition according to any one of (1) to (11).

(14) A liquid crystal alignment film obtained by using the liquid crystal alignment treatment agent according to (13) above.

(15) A liquid crystal alignment film obtained by the ink jet method using the liquid crystal alignment treatment agent according to (13) above.

(16) A liquid crystal display element having the liquid crystal alignment film according to (14) or (15) above.

(17) A liquid crystal composition comprising a liquid crystal layer between a pair of substrates provided with electrodes, and a polymerizable compound capable of polymerizing at least one of active energy rays and heat between the pair of substrates, The liquid crystal alignment film according to (14) or (15) above, which is used for a liquid crystal display device manufactured through a process of polymerizing the polymerizable compound while applying a voltage between the electrodes.

(18) A liquid crystal display element having the liquid crystal alignment film according to (17) above.

(19) A liquid crystal alignment film comprising a liquid crystal layer between a pair of substrates provided with electrodes, the liquid crystal alignment film including a polymerizable group capable of polymerizing at least one of active energy rays and heat between the pair of substrates, The liquid crystal alignment film according to (14) or (15) above, which is used for a liquid crystal display device manufactured through a process of polymerizing the polymerizable group while applying a voltage between electrodes.

(20) A liquid crystal display element having the liquid crystal alignment film according to (19) above.

The composition containing the solvent having the specific structure of the present invention and the polysiloxane obtained from the alkoxysilane having the specific structure can suppress the occurrence of pinholes when the resin film is formed and further, Can be provided as a high composition.

Further, by using the composition of the present invention as a liquid crystal alignment treatment agent, occurrence of pinholes can be suppressed, and further, a liquid crystal alignment film having a step-following ability with respect to the unevenness of the stepped substrate can be provided. Further, the liquid crystal alignment treatment agent of the present invention can provide a liquid crystal alignment film capable of exhibiting a stable pretilt angle even after exposure to high temperature and light for a long time. Therefore, the liquid crystal display element having the liquid crystal alignment film obtained from the liquid crystal alignment treatment agent of the present invention is excellent in reliability, and can be suitably used for a large-screen liquid crystal television, a medium-sized car navigation system, or a smart phone.

1 is a view showing a stepped substrate provided with a resin coating obtained by applying the composition of the present invention.

As a result of intensive studies, the present inventors have obtained the following findings and have completed the present invention.

The present invention relates to a composition containing the following components (A) and (B), a liquid crystal alignment treatment agent, a resin film obtained by using the composition, a liquid crystal alignment film obtained by using the liquid crystal alignment treatment agent, To a liquid crystal display element.

(A): a solvent represented by the following formula [1] (also referred to as a specific solvent);

[Chemical Formula 8]

(In the formula [1], X ¹ and X ² each independently represent an alkyl group having 1 to 3 carbon atoms, and X ³ and X ⁴ each independently represent an alkyl group having 1 to 3 carbon atoms.

(B): polysiloxane (also referred to as a specific polysiloxane) obtained by polycondensation of an alkoxysilane containing at least one selected from alkoxysilanes represented by the following formulas [2a], [2b] and [2c]

[Chemical Formula 9]

(In the formula [2a], A ¹ represents at least one structure selected from the structures represented by the following formulas [2a-1] and [2a-2] ² are, each independently, a hydrogen atom or an alkyl group having a carbon number of 1 ~ 5, a ³ each independently represents an alkyl group having a carbon number of 1 ~ 5, m ¹ represents an integer of 1 or 2, n ¹ is 0 to P ¹ represents an integer of 0 to 3, provided that m ¹ + n ¹ + p ¹ represents an integer of 4).

[Chemical formula 10]

(Formula [2a-1] of the, Y ¹ represents a single _{bond, - (CH 2) a -} (a is an integer of 1 ~ 15), -O-, -CH 2 O-, -CONH-, -NHCO- _{, -CON (CH 3) -,} -N (CH 3) CO-, represents a coupler of at least one member selected from -COO- and -OCO-, Y ² is a single bond or - (CH _{2) b} - ( b is an integer of 1 to 15, Y ³ is a single bond, - (CH ₂ ) _c - (c is an integer of 1 to 15), -O-, -CH ₂ O-, -COO- and -OCO-, Y ⁴ is at least one cyclic group selected from a benzene ring, a cyclohexane ring and a heterocyclic ring, or a divalent organic group having a carbon number of 17 to 51 and having a steroid skeleton, And any hydrogen atom on the cyclic group is substituted with an alkyl group having 1 to 3 carbon atoms, an alkoxyl group having 1 to 3 carbon atoms, a fluorine-containing alkyl group having 1 to 3 carbon atoms, a fluoro-containing alkoxyl group having 1 to 3 carbon atoms, and, Y ⁵ is a benzene ring, a cyclohexane An alkyl group having 1 to 3 carbon atoms, an alkoxyl group having 1 to 3 carbon atoms, a fluorine-containing alkyl group having 1 to 3 carbon atoms, a fluorine-containing alkyl group having 1 to 3 carbon atoms, A fluorine-containing alkoxyl group having 1 to 3 carbon atoms or a fluorine atom, n is an integer of 0 to 4, Y ⁶ is an alkyl group having 1 to 22 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, an alkenyl group having 1 to 22 carbon atoms A fluorine-containing alkyl group, an alkoxyl group having 1 to 22 carbon atoms, and a fluorinated alkoxyl group having 1 to 22 carbon atoms.

(11)

(In the formula [2a-2], Y ⁷ represents a single bond, -O-, -CH ₂ O-, -CONH-, -NHCO-, -CON (CH ₃ ) -, -N (CH ₃ ) -COO- and -OCO-, and Y ⁸ represents an alkyl group having 8 to 22 carbon atoms or a fluorine-containing alkyl group having 6 to 18 carbon atoms.

[Chemical Formula 12]

(Wherein, in the formula [2b], B ¹ each independently represents a carbon number having at least one kind selected from a vinyl group, an epoxy group, an amino group, a mercapto group, an isocyanate group, a methacrylic group, an acrylic group, an ureido group and a cinnamoyl group represents an organic group of ² ~ 12, B 2 each independently represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, B ³ are each independently, an alkyl group or an alkoxyalkyl group of 1 to 5 carbon atoms of 1 to 5 carbon atoms , m ² represents an integer of 1 or 2, n ² represents an integer of 0 to 2, and p ² represents an integer of 0 to 3, provided that m ² + n ² + p ² represents an integer of 4 ).

[Chemical Formula 13]

(Wherein, in the formula [2c], D ¹ each independently represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, D ² each independently represents an alkyl group having 1 to 5 carbon atoms, and n ³ denotes an integer of 0 to 3 .

The specific solvent of the present invention has a higher viscosity as a solvent than an alcohol-based or glycol-based solvent usually used in a polysiloxane-based polymer. Therefore, the composition using the specific solvent of the present invention and the liquid crystal alignment treatment agent (collectively referred to as a coating solution) have high coating properties against foreign substances having nuclei on the substrate when they are coated on the substrate, It is possible to obtain a resin coating film and a liquid crystal alignment film capable of suppressing the occurrence of the problems. Further, from the above reasons, the coating solution using the specific solvent of the present invention has a higher step-wise followability to the unevenness of the substrate step difference, so that a resin film having a uniform film thickness or a liquid crystal alignment film can be obtained.

The specific solvent of the present invention has a lower surface tension than N-methyl-2-pyrrolidone (also referred to as NMP) or? -Butyrolactone (also referred to as? -BL), which has high viscosity as a solvent. Therefore, the coating solution using the specific solvent of the present invention has a high wettability to a foreign substance (for example, blurring of oil) without nucleus, so that the resin coating capable of suppressing the occurrence of cratering and the liquid crystal alignment film Can be obtained.

In addition, the component (B) of the present invention is a polysiloxane obtained by polycondensation of an alkoxysilane containing at least one selected from alkoxysilanes represented by the above-mentioned formulas [2a], [2b] and [2c]. Among them, in the case where the composition of the present invention is used as a liquid crystal alignment film by using the composition of the present invention as a liquid crystal alignment treatment agent, it is preferable that A ¹ in the formula [2a] is a polysiloxane using an alkoxysilane having a specific side chain structure represented by the formula [2a- Do. This specific side chain structure has a divalent cyclic group of a benzene ring, a cyclohexyl ring or a heterocyclic ring, or a divalent organic group having a carbon number of 17 to 51 and having a steroid skeleton in the side chain portion. These divalent cyclic groups of the benzene ring, cyclohexyl ring or heterocyclic ring, or divalent organic groups having the carbon number of 17 to 51 having a steroid skeleton exhibit a rigid structure as compared with the long chain alkyl groups of the prior art. As a result, the stability of the side chain portion against heat and ultraviolet rays is improved, and a liquid crystal alignment film having a stable tilt angle with respect to heat or light is obtained.

In view of the above, a composition containing a specific solvent and a specific polysiloxane of the present invention is a composition capable of forming a resin coating film having excellent coatability.

In addition, the liquid crystal alignment treatment agent of the present invention can provide a liquid crystal alignment film having excellent film properties, and further, a liquid crystal alignment film capable of exhibiting a stable pretilt angle even after exposure to high temperature and light irradiation for a long time. Therefore, by using this liquid crystal alignment film, a liquid crystal display device having excellent display characteristics and high reliability can be obtained.

Hereinafter, embodiments of the present invention will be described in detail.

<Specific solvent>

The specific solvent of the present invention is a solvent represented by the following formula [1].

[Chemical Formula 14]

X ¹ and X ² each independently represent an alkyl group having 1 to 3 carbon atoms (for example, a methyl group, an ethyl group, a propyl group or an isopropyl group), preferably a methyl group or an ethyl group, Particularly preferably a methyl group.

In the formula [1], X ³ and X ⁴ each independently represent an alkyl group having 1 to 3 carbon atoms (for example, a methyl group, an ethyl group, a propyl group or an isopropyl group), preferably a methyl group or an ethyl group, Particularly preferably a methyl group.

Specifically, it is preferable that it is represented by the following formula [1a].

[Chemical Formula 15]

The specific solvent of the present invention is preferably 10 to 90% by mass of the total solvent contained in the composition and the liquid crystal alignment treatment agent in order to enhance the effect of increasing the step-wise followability and the wettability to the unevenness of the substrate of the above- Do. Among these, 15 to 80 mass% is preferable. More preferably, it is from 20 to 80% by mass, and more preferably from 30 to 70% by mass.

The greater the amount of the specific solvent of the present invention in the composition and the solvent in the liquid crystal alignment treatment agent, the higher the effect of the present invention is, and the resin coating film and liquid crystal alignment film excellent in coating film property can be obtained.

<Specific polysiloxane>

The specific polysiloxane as the component (B) of the present invention is a polysiloxane obtained by polycondensation of an alkoxysilane containing at least one selected from alkoxysilanes represented by the following formulas [2a], [2b] and [2c] .

The alkoxysilane represented by the formula [A1] of the present invention is an alkoxysilane having a structure represented by the following formula [A1].

[Chemical Formula 16]

In formula [2a], A ¹ represents at least one specific side chain structure selected from the structures represented by the following formulas [2a-1] and [2a-2].

[Chemical Formula 17]

In formula [2a-1], Y ¹ represents a single bond, - (CH ₂ ) _a - (a is an integer of 1 to 15), -O-, -CH ₂ O-, -CONH-, -NHCO-, _{-CON (CH 3) -, -N} (CH 3) represents a coupler at least of one kind selected from CO-, -COO- and -OCO-. Among them, a single bond, - (CH ₂ ) _a - (a is an integer of 1 to 15), -O-, -CH ₂ O- or -COO- is preferable in view of availability of raw materials and ease of synthesis desirable. More preferably, it is a single bond, - (CH ₂ ) _a - (a is an integer of 1 to 10), -O-, -CH ₂ O- or -COO-.

In the formula [2a-1], Y ² represents a single bond or - (CH ₂ ) _b - (b is an integer of 1 to 15). Among them, a single bond or - (CH ₂ ) _b - (b is an integer of 1 to 10) is preferable.

In formula [2a-1], Y ³ represents a single bond, - (CH ₂ ) _c - (c is an integer of 1 to 15), -O-, -CH ₂ O-, -COO- and -OCO- Represents at least one kind of bonding group selected. Among them, a single bond, - (CH ₂ ) _c - (c is an integer of 1 to 15), -O-, -CH ₂ O- or -COO- is preferable from the viewpoint of easiness of synthesis. More preferably, it is a single bond, - (CH ₂ ) _c - (c is an integer of 1 to 10), -O-, -CH ₂ O- or -COO-.

In formula [2a-1], Y ⁴ is at least one bivalent cyclic group selected from a benzene ring, a cyclohexane ring and a heterocyclic ring, and any hydrogen atom on these cyclic groups may be substituted with an alkyl group having 1 to 3 carbon atoms, An alkoxyl group having 1 to 3 carbon atoms, a fluorinated alkyl group having 1 to 3 carbon atoms, a fluorinated alkoxyl group having 1 to 3 carbon atoms, or a fluorine atom. Y ⁴ may be a divalent organic group selected from organic groups having a steroid skeleton and having 17 to 51 carbon atoms. Among them, a divalent cyclic group of a benzene ring or a cyclohexane ring, or a divalent organic group of a carbon number of 17 to 51 having a steroid skeleton is preferable from the viewpoint of ease of synthesis.

In formula [2a-1], Y ⁵ represents at least one bivalent cyclic group selected from a benzene ring, a cyclohexane ring and a heterocyclic ring, and any hydrogen atom in these cyclic groups may be substituted with an alkyl group having 1 to 3 carbon atoms, An alkoxyl group having 1 to 3 carbon atoms, a fluorinated alkyl group having 1 to 3 carbon atoms, a fluorinated alkoxyl group having 1 to 3 carbon atoms, or a fluorine atom. Among them, a benzene ring or a cyclohexane ring is preferable.

In the formula [2a-1], n represents an integer of 0 to 4. Among them, from the viewpoint of availability of raw materials and easiness of synthesis, 0 to 3 is preferable. More preferred is 0 to 2.

In the formula [2a-1], Y ⁶ represents an alkyl group having 1 to 22 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, a fluorine-containing alkyl group having 1 to 22 carbon atoms, an alkoxyl group having 1 to 22 carbon atoms, And an alkoxyl group. Among them, an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, a fluorine-containing alkyl group having 1 to 10 carbon atoms, an alkoxyl group having 1 to 18 carbon atoms, or a fluorinated alkoxyl group having 1 to 10 carbon atoms is preferable. More preferably an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, or an alkoxyl group having 1 to 12 carbon atoms. And particularly preferably an alkyl group having 1 to 9 carbon atoms or an alkoxyl group having 1 to 9 carbon atoms.

Preferred combinations of Y ¹ to Y ⁶ and n in the formula [2a-1] are those listed in Tables 6 to 47 of pages 13 to 34 of International Publication No. 2011/132751 (published on October 21, 2011) (2-1) to (2-629). In addition, in each table of International Publication, there is a Y ¹ ~ Y ⁶ in the present invention, shown as Y1 ~ Y6, Y1 ~ Y6 is by reading change as Y ¹ ~ Y ^6. In (2-605) to (2-629) listed in the tables of International Publication, the organic group having a steroid skeleton and having a carbon number of 17 to 51 in the present invention is preferably an organic group having a steroid skeleton and having a carbon number of 12 to 25 Organic group, and the organic group having 12 to 25 carbon atoms having a steroid skeleton is replaced with an organic group having a steroid skeleton and having 17 to 51 carbon atoms.

[Chemical Formula 18]

In formula [2a-2], Y ⁷ represents a single bond, -O-, -CH ₂ O-, -CONH-, -NHCO-, -CON (CH ₃ ) -, -N (CH ₃ ) COO- and -OCO-. Among them, a single bond, -O-, -CH ₂ O-, -CONH-, -CON (CH ₃ ) - or -COO- is preferable. More preferably, it is a single bond, -O-, -CONH- or -COO-.

In the formula [2a-2], Y ⁸ represents an alkyl group having 8 to 22 carbon atoms or a fluorine-containing alkyl group having 6 to 18 carbon atoms. Among them, an alkyl group having 8 to 18 carbon atoms is preferable.

In the specific side chain structure of the present invention, it is preferable to use the structure represented by the formula [2a-1] in that a high and stable liquid crystal alignment property can be obtained.

In formula [2a], each A ² independently represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. Among them, a hydrogen atom or an alkyl group having 1 to 3 carbon atoms is preferable.

In formula [2a], each A ³ is independently an alkyl group having 1 to 5 carbon atoms. Among them, an alkyl group having 1 to 3 carbon atoms is preferable in view of reactivity of polycondensation.

In formula [2a], m ¹ is an integer of 1 or 2. Among them, 1 is preferable in terms of synthesis.

In formula [2a], n ¹ is an integer of 0 to 2.

In formula [2a], p ¹ is an integer of 0 to 3. Among them, an integer of 1 to 3 is preferable in view of the reactivity of polycondensation. More preferably 2 or 3.

In formula [2a], m ¹ + n ¹ + p ¹ is an integer of 4.

Specific examples of the specific alkoxysilane (a) represented by the formula [2a] include alkoxysilanes represented by the following formulas [a-1] to [a-32].

[Chemical Formula 19]

(Wherein R ¹ , R ³ , R ⁵ and R ⁷ each independently represents an alkyl group having 1 to 3 carbon atoms, and the groups represented by the formulas [a-1] to [a-4] a-4], each of R ² , R ⁴ , R ⁶ and R ⁸ independently represents an alkyl group having 1 to 3 carbon atoms, and m in the formulas [a-1] to [ Independently represents 0 or 1, with the proviso that m + n is 3), wherein R &lt; 1 &gt; and R &lt; 3 &gt;

[Chemical Formula 20]

(Wherein R ¹ , R ³ , R ⁵ and R ⁷ each independently represents an alkyl group having 1 to 3 carbon atoms, and the groups represented by formulas [a-5] to [a-8] , R ² , R ⁴ , R ⁶ and R ⁸ each independently represent an alkyl group having 1 to 3 carbon atoms, and m in the formulas [a-5] to [a-8] , And n represents, independently of each other, 0 or 1, with the proviso that m + n is 3, in the formulas (a-5) to (a-8).

[Chemical Formula 21]

(Wherein R ¹ , R ³ , R ⁵ and R ⁷ each independently represents an alkyl group having 1 to 3 carbon atoms, and the groups represented by the formulas [a-9] to [ a-12], each of R ² , R ⁴ , R ⁶ and R ⁸ independently represents an alkyl group having 1 to 3 carbon atoms, and in the formulas [a-9] to [ And n and n independently represent 0 or 1, with the proviso that m + n is 3, and R &lt; 2 &gt;

[Chemical Formula 22]

(In formulas [a-13] to [a-16], R ¹ , R ³ , R ⁵ and R ⁷ each independently represent an alkyl group having 1 to 3 carbon atoms, a-16], each of R ² , R ⁴ , R ⁶ and R ⁸ independently represents an alkyl group having 1 to 3 carbon atoms, and in the formulas [a-13] to [ , And n represents an integer of 0 or 1, with the proviso that m + n is 3).

(23)

(In the formulas [a-17] and [a-18], R ¹ and R ³ each independently represent an alkyl group having 1 to 3 carbon atoms, R ² and R ⁴ each independently represent an alkyl group having 1 to 3 carbon atoms, and each of m in the formula [a-17] and the formula [a-18] represents 2 or 3, 17] and formula [a-18], n represents, independently of each other, 0 or 1, provided that m + n is 3.

&Lt; EMI ID =

(Wherein R ¹ , R ⁵ , R ⁹ and R ¹³ each independently represents an alkyl group having 1 to 3 carbon atoms, and the groups represented by the formulas [a-19] to [ a-22], R ² , R ⁶ , R ¹⁰ and R ¹⁴ each independently represent an alkyl group having 1 to 3 carbon atoms, and R ³ , R ⁷ , R ¹¹ and R ¹⁵ each independently represent -O-, -COO-, -OCO-, -CONH-, -NHCO-, -CON (CH ₃ ) -, -N (CH ₃ ) _{OCH 2 -, -CH 2 O-,} -COOCH 2 - , and represents at least one coupler of one kind selected from -CH ₂ OCO-, formula [a-19] ~ formula ^{[a-22], R 4} , R ⁸ , R ¹² and R ¹⁶ each independently represent an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a fluorine-containing alkyl group having 1 to 12 carbon atoms, or a fluorine-containing alkoxy group having 1 to 12 carbon atoms, M] each independently represents 2 or 3, and in the formulas [a-19] to [a-22], n independently represents 0 or 1 , Provided that m + n Is 3, and the cis-trans isomers of 1,4-cyclohexylene in the formulas [a-20] to [a-22] represent trans isomers, respectively.

(25)

(In formulas [a-23] and [a-24], R ¹ and R ⁵ each independently represent an alkyl group having 1 to 3 carbon atoms, R ² and R ⁶ each independently represent an alkyl group having 1 to 3 carbon atoms, and in the formula [a-23] and the formula [a-24], R ³ and R ⁷ each independently represent -O-, -COO -, -OCO-, -CONH-, -NHCO-, -CON (CH 3) -, -N (CH 3) CO-, -OCH 2 -, -CH 2 O-, -COOCH 2 - and -CH ₂ OCO-. In formulas [a-23] and [a-24], R ⁴ and R ⁸ each independently represent an alkyl group having 1 to 12 carbon atoms, an alkyl group having 1 to 12 carbon atoms An alkyl group having 1 to 12 carbon atoms, a fluorine-containing alkoxy group having 1 to 12 carbon atoms, a fluorine group, a cyano group, a trifluoromethyl group, a nitro group, an azo group, a formyl group, an acetyl group, M is at least 2 independently selected from the group consisting of 2 or 3; 3, and n in each of the formulas [a-23] and [a-24] represents independently 0 or 1, provided that m + n is 3.

(26)

(Wherein R ¹ , R ⁵ , R ⁹ and R ¹³ each independently represents an alkyl group having 1 to 3 carbon atoms, and the groups represented by the formulas [a-25] to [ , R ² , R ⁶ , R ¹⁰ and R ¹⁴ each independently represents an alkyl group having 1 to 3 carbon atoms, and R ³ , R ⁷ , R ¹¹ and R ¹⁵ each independently represent -O-, -COO-, -OCO-, -CONH-, -NHCO-, -CON (CH ₃ ) -, -N (CH ₃ ) _{OCH 2 -, -CH 2 O-,} -COOCH 2 - , and represents at least one coupler of one kind selected from -CH ₂ OCO-, formula [a-25] ~ formula ^{[a-28], R 4} , R ⁸ , R ¹² and R ¹⁶ each independently represent an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a fluorine-containing alkyl group having 1 to 12 carbon atoms, or a fluorine-containing alkoxy group having 1 to 12 carbon atoms, -25] to formula [a-28], each of m independently represents 2 or 3, and n in each of formulas [a-25] to [a-28] independently represents 0 or 1 , Provided that m + n Is 3, and the cis-trans isomers of 1,4-cyclohexylene in the formulas [a-26] to [a-28] represent trans isomers, respectively.

(27)

(Wherein R ¹ , R ⁵ and R ⁹ each independently represents an alkyl group having 1 to 3 carbon atoms, and the groups represented by formulas [a-29] to [a-31] , R ² , R ⁶ and R ¹⁰ each independently represents an alkyl group having 1 to 3 carbon atoms, and R ³ , R ⁷ and R ¹¹ in the formulas [a-29] to [a-31] Independently, -O-, -COO-, -OCO-, -CONH-, -NHCO-, -CON (CH ₃ ) -, -N (CH ₃ ) CO-, -OCH ₂ -, -CH ₂ O- , -COOCH ₂ - and -CH ₂ OCO-. In the formulas [a-29] to [a-31], R ⁴ , R ⁸ and R ¹² each independently represent a hydrogen atom, An alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a fluorine-containing alkyl group having 1 to 12 carbon atoms, or a fluorinated alkoxy group having 1 to 12 carbon atoms, m represents independently 2 or 3, and n in each of the formulas [a-29] to [a-31] represents independently 0 or 1 with the proviso that m + n is 3, [a-29] Formula [a-31] 1,4- cyclo hexylene the sheath of the -trans reason, each represents a trans isomer).

(28)

(In the formula [a-32], R ¹ represents an alkyl group having 1 to 3 carbon atoms, R ² represents an alkyl group having 1 to 3 carbon atoms, m represents 2 or 3, and n represents 0 or 1 , M + n is 3, B ¹⁴ is an alkyl group having 3 to 20 carbon atoms which may be substituted with a fluorine atom, B ¹³ is a 1,4-cyclohexylene group or a 1,4-phenylene group, B ¹² represents an oxygen atom or COO- * (provided that a bonding hand to which &quot; * &quot; is bonded is bonded to B ³ ), B ¹¹ represents an oxygen atom or COO- * ₂ ) a ² ), a ¹ represents an integer of 0 or 1, a ² represents an integer of 2 to 10, and a ³ represents an integer of 0 or 1.

Further, it is also possible to use a silane coupling agent such as octyltrimethoxysilane, octyltriethoxysilane, decyltrimethoxysilane, dodecyltrimethoxysilane, dodecyltriethoxysilane, hexadecyltrimethoxysilane, hexadecyltriethoxysilane, Heptadecyltrimethoxysilane, octadecyltrimethoxysilane, octadecyltrimethoxysilane, nonadecyltrimethoxysilane, nonadecyltriethoxysilane, isooctyltriethoxy silane, heptadecyltrimethoxysilane, octadecyltrimethoxysilane, octadecyltrimethoxysilane, Silane, pentafluorophenylpropyltrimethoxysilane, triethoxy-1H, 1H, 2H, 2H-tridecafluoro-n-octylsilane and the like.

The alkoxysilane represented by the formula [2a] of the present invention can be used in a wide variety of fields, such as solubility in a solvent of the specific polysiloxane of the present invention, applicability of the composition and liquid crystal alignment treatment agent, Depending on the properties such as charge accumulation, one type or two or more types can be mixed and used.

The alkoxysilane represented by the formula [2b] of the present invention is an alkoxysilane having a structure represented by the following formula [2b].

[Chemical Formula 29]

In formula [2b], B ¹ each independently represents a group having 2 or more carbon atoms having at least one kind selected from a vinyl group, an epoxy group, an amino group, a mercapto group, an isocyanate group, a methacrylic group, an acrylic group, an ureido group and a cinnamoyl group &Lt; / RTI &gt; to 12 organic groups. Among them, a vinyl group, an epoxy group, an amino group, a methacrylic group, an acrylic group or a ureido group is preferable in view of easiness of obtaining. More preferably, it is a methacryl group, an acrylic group or a ureido group.

In the formula [2b], each of B ² independently represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. Among them, a hydrogen atom or an alkyl group having 1 to 3 carbon atoms is preferable.

In the formula [2b], each B ³ independently represents an alkyl group having 1 to 5 carbon atoms or an alkoxyalkyl group having 1 to 5 carbon atoms. Among them, an alkyl group having 1 to 3 carbon atoms is preferable in view of reactivity of polycondensation.

In the formula [2b], m ² represents an integer of 1 or 2. Among them, 1 is preferable in terms of synthesis.

In the formulas [2b], n ² represents an integer of 0-2.

In the formula [2b], p ² represents an integer of 0 to 3. Among them, an integer of 1 to 3 is preferable in view of the reactivity of polycondensation. More preferably 2 or 3.

In the formula [2b], m ² + n ² + p ² represents an integer of 4.

Specific examples of the alkoxysilane represented by the formula [2b] include allyltriethoxysilane, allyltrimethoxysilane, diethoxymethylvinylsilane, dimethoxymethylvinylsilane, triethoxyvinylsilane, vinyltrimethoxysilane, Vinyltris (2-methoxyethoxy) silane, m-styrylethyltriethoxysilane, p-styrylethyltriethoxysilane, m-styrylmethyltriethoxysilane, p-styrylmethyltriethoxy Silane, 3- (N-styrylmethyl-2-aminoethylamino) propyltrimethoxysilane, diethoxy (3-glycidyloxypropyl) methylsilane, 3-glycidyloxypropyl (dimethoxy) (3-glycidyloxypropyltrimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3- (2-aminoethylamino) propyldimethoxymethylsilane, 3- Aminoethylamino) propyltriethoxysilane, 3- (2-aminoethylamino) propyltrimethoxysilane, 3-aminopropyldiethoxymethylsilane, 3-amino (Trimethoxy) methylsilane, 3-aminopropyltrimethoxysilane, trimethoxy [3- (phenylamino) propyl] silane, 3-mercaptopropyl (Triethoxysilyl) propyl methacrylate, 3- (triethoxysilyl) propyl methacrylate, 3- (trimethoxysilyl) propyl methacrylate, (Triethoxysilyl) propyl acrylate, 3- (trimethoxysilyl) propyl acrylate, 2- (triethoxysilyl) ethyl methacrylate, 2- (Triethoxysilyl) ethyl acrylate, 2- (trimethoxysilyl) ethyl acrylate, (triethoxysilyl) methyl methacrylate, (trimethoxysilyl) methyl methacrylate, Ethoxysilyl) methyl acrylate, (trimethoxysilyl) methyl acrylate,? -Ureidopropyltri (R) -N-1-phenylethyl-N'-triethoxysilylpropylurea, γ-ureidopropyltrimethoxysilane, γ-ureidopropyltripropoxysilane, Phenylethyl-N'-trimethoxysilylpropylurea, and the like.

Among them, allyltriethoxysilane, allyltrimethoxysilane, diethoxymethylvinylsilane, dimethoxymethylvinylsilane, triethoxyvinylsilane, vinyltrimethoxysilane, vinyltris (2-methoxyethoxy) silane (Trimethoxysilyl) propyl methacrylate, 3- (trimethoxysilyl) propyl methacrylate, 3- (trimethoxysilyl) propyl acrylate, 3- Methylsilane, 3-glycidyloxypropyl (diethoxy) methylsilane, 3-glycidyloxypropyltrimethoxysilane or 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane is preferable.

The alkoxysilane represented by the formula [2b] of the present invention can be produced by a process comprising the steps of dissolving the specific polysiloxane of the present invention in a solvent, coating properties of the composition and the liquid crystal alignment treatment agent, and further aligning the liquid crystal, Depending on the properties such as charge accumulation, one type or two or more types can be mixed and used.

The alkoxysilane represented by the formula [2c] of the present invention is an alkoxysilane having a structure represented by the following formula [2c].

(30)

In the formula [2c], D ¹ represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, but they may be substituted with a halogen atom, a nitrogen atom, an oxygen atom or a sulfur atom. Among them, D ¹ is preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

In the formula [2c], D ² represents an alkyl group having 1 to 5 carbon atoms. Among them, an alkyl group having 1 to 3 carbon atoms is preferable in view of reactivity of polycondensation.

In the formula [2c], n represents an integer of 0 to 3.

Specific examples of the alkoxysilane represented by the formula [2c] include tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane, tetrabutoxysilane, methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxy Examples of the silane coupling agent include silane, ethyltriethoxysilane, propyltrimethoxysilane, propyltriethoxysilane, methyltripropoxysilane, dimethyldimethoxysilane, dimethyldiethoxysilane, diethoxydiethylsilane, dibutoxydimethylsilane, ) Triethoxysilane, 3-chloropropyldimethoxymethylsilane, 3-chloropropyltriethoxysilane, 2-cyanoethyltriethoxysilane, trimethoxy (3,3,3-trifluoropropyl) silane Or 3-trimethoxysilylpropyl chloride.

Examples of the alkoxysilane represented by the formula [2c] wherein n is 0 include tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane or tetrabutoxysilane, and alkoxysilane represented by the formula [2c] , It is preferable to use these alkoxysilanes.

The alkoxysilane represented by the formula [2c] of the present invention can be obtained by a process comprising the steps of dissolving the specific polysiloxane of the present invention in a solvent, coating properties of the composition and the liquid crystal alignment treatment agent, and further aligning properties of the liquid crystal, Depending on the properties such as charge accumulation, one type or two or more types can be mixed and used.

The specific polysiloxane of the present invention is a polysiloxane obtained by polycondensation of an alkoxysilane containing at least one selected from alkoxysilanes represented by the above-mentioned formula [2a], formula [2b] or formula [2c] Polysiloxane obtained by polycondensation of an alkoxysilane containing a species is preferable. That is, polysiloxane obtained by polycondensation of two types of alkoxysilanes represented by the above-mentioned formulas [2a] and [2b], polysiloxane obtained by polycondensation of two types of alkoxysilanes represented by the above formulas [2a] Polysiloxane obtained by polycondensation of two types of alkoxysilanes represented by the above formulas [2b] and [2c], and polysiloxane obtained by polycondensation of three types of alkoxysilanes represented by the above formulas [2a], [2b] &Lt; / RTI &gt; Among them, polysiloxane obtained by polycondensation of two types of alkoxysilanes represented by formulas [2a] and [2b], polysiloxane obtained by polycondensation of two types of alkoxysilanes represented by formulas [2a] and [2c], and A polysiloxane obtained by polycondensing three kinds of alkoxysilanes represented by the formulas [2a], [2b] and [2c] is preferable.

When the hydrophobic property of the resin film obtained from the composition of the present invention is enhanced or when the liquid crystal alignment film obtained from the liquid crystal alignment treatment agent of the present invention is used in a liquid crystal display device for displaying liquid crystal aligned vertically, Among the combinations, it is preferable to use a polysiloxane using the alkoxysilane of the above formula [2a].

When a plurality of alkoxysilanes are used in the preparation of the specific polysiloxane of the present invention, the alkoxysilane represented by the formula [2a] is preferably 1 to 40 mol%, more preferably 1 To 30 mol%. The alkoxysilane represented by the formula [2b] is preferably 1 to 70 mol%, more preferably 1 to 60 mol%, of all the alkoxysilanes. The alkoxysilane represented by the formula [2c] is preferably 1 to 99 mol%, more preferably 1 to 80 mol%, of all the alkoxysilanes.

The method for obtaining the specific polysiloxane used in the present invention is not particularly limited. The specific polysiloxane in the present invention is obtained by polymerizing an alkoxysilane containing any one of the alkoxysilanes represented by the above formula [2a], formula [2b] or formula [2c] in a solvent, , Alkoxysilanes represented by the formulas [2b] and [2c] in a solvent. In addition, the specific polysiloxane of the present invention is obtained as a solution in which alkoxysilane is polycondensed and uniformly dissolved in a solvent.

The method of polycondensation of the specific polysiloxane of the present invention is not particularly limited. For example, a method of subjecting alkoxysilane to a hydrolysis / polycondensation reaction in a specific solvent, an alcohol solvent or a glycol solvent of the present invention. At this time, the hydrolysis-polycondensation reaction may be partially hydrolyzed or completely hydrolyzed. In the case of complete hydrolysis, in theory, water of 0.5 times the molar amount of all alkoxy groups in the alkoxysilane may be added, but it is usually preferable to add an excess amount of water in an amount of 0.5 times the molar amount. In order to obtain the specific polysiloxane of the present invention, the amount of water used in the hydrolysis and polycondensation reaction may be appropriately selected according to the purpose, but is preferably 0.5 to 2.5 times the molar amount of all the alkoxy groups in the alkoxysilane.

For the purpose of accelerating the hydrolysis and polycondensation reaction, an acidic compound such as hydrochloric acid, sulfuric acid, nitric acid, acetic acid, formic acid, oxalic acid, maleic acid or fumaric acid, ammonia, methylamine, ethylamine, ethanolamine or triethylamine Or a catalyst such as a metal salt such as hydrochloric acid, nitric acid or nitric acid can be used. In addition, the hydrolysis-polycondensation reaction may be promoted by heating the solution in which the alkoxysilane is dissolved. At that time, the heating temperature and the heating time can be appropriately selected depending on the purpose. For example, heating and stirring at 50 DEG C for 24 hours, and then heating and stirring for 1 hour under reflux.

As another method of polycondensation, a method of polycondensation reaction by heating a mixture of alkoxysilane, a solvent and oxalic acid can be mentioned. Specifically, oxalic acid is added to a specific solvent, an alcohol solvent or a glycol-based solvent of the present invention in advance to prepare a solution of oxalic acid, and then the solution is heated to mix the alkoxysilane. At this time, the amount of oxalic acid to be used in the above reaction is preferably 0.2 to 2.0 mol per 1 mol of all alkoxy groups in the alkoxysilane. This reaction can be carried out at a temperature of the solution of 50 to 180 DEG C, but it is preferably carried out for several tens of minutes to several tens of hours under reflux so as not to evaporate or volatilize the solvent.

In the case of using a plurality of alkoxysilanes represented by the formulas [2a], [2b] and [2c] in the polycondensation reaction for obtaining the specific polysiloxane of the present invention, a mixture obtained by premixing a plurality of alkoxysilanes Or may be reacted while sequentially adding a plurality of kinds of alkoxysilanes.

The solvent to be used in the polycondensation reaction of the alkoxysilane is not particularly limited as long as it contains the specific solvent of the present invention and dissolves the alkoxysilane. In addition, any solvent that does not dissolve alkoxysilane may be used as long as it dissolves with progress of polycondensation reaction of alkoxysilane. As a solvent to be used in the polycondensation reaction, an alcohol is generally generated by a polycondensation reaction of an alkoxysilane, and thus a solvent having good compatibility with an alcohol solvent, a glycol solvent, a glycol ether solvent or an alcohol is used . Specific examples of the solvent used in such a polycondensation reaction include alcohol solvents such as methanol, ethanol, propanol, butanol or diacetone alcohol, alcohols such as ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, hexylene glycol, Butanediol, 1,3-butanediol, 2,3-butanediol, 1,2-pentanediol, 1,3-pentanediol, 1,4-pentanediol Glycol solvents such as diol, 1,5-pentanediol, 2,4-pentanediol, 2,3-pentanediol or 1,6-hexanediol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono Propylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monoethyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dipropyl ether, ethylene glycol dibutyl ether, Propyl ether, Ethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether , Glycol ether solvents such as propylene glycol monobutyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, propylene glycol dipropyl ether or propylene glycol dibutyl ether, N-methyl-2-pyrrolidone, Is mixed with an alcohol such as 2-pyrrolidone,? -Butyrolactone, N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, tetramethylurea, hexamethylphosphotriapamide or m- A good solvent may be mentioned.

In the present invention, these solvents used in the polycondensation reaction may be used alone or in combination of two or more.

Solution polymerization of a specific polysiloxane obtained by the above method, it is preferred that (also referred to as SiO ₂ in terms of concentration) the total alkoxy silane is in terms of a silicon atom having a SiO ₂ concentration of injected as a raw material, 20 mass% or less. In particular, it is preferably 5 to 15% by mass. By selecting an arbitrary concentration in this concentration range, the generation of gel in the solution can be suppressed, and a uniform polycondensation solution of the specific polysiloxane can be obtained.

In the present invention, the polycondensation solution of the specific polysiloxane obtained by the above method may be directly used as the solution of the specific polysiloxane of the component (B) of the present invention. If necessary, the polycondensation solution of the specific polysiloxane obtained by the above- Or may be diluted by adding a solvent, or may be replaced with another solvent to obtain a solution of the specific polysiloxane of the component (B).

The solvent (also referred to as an addition solvent) to be used in the dilution by adding the above solvent may be a solvent used for the polycondensation reaction or other solvent. The addition solvent is not particularly limited as long as the specific polysiloxane is uniformly dissolved, and one or more kinds of the addition solvent may be arbitrarily selected and used. Such an addition solvent may be a ketone solvent such as acetone, methyl ethyl ketone or methyl isobutyl ketone, an ester solvent such as methyl acetate, ethyl acetate or ethyl lactate, or the like, in addition to the solvent used in the above polycondensation reaction .

<Composition / liquid crystal alignment treatment agent>

The composition of the present invention and the liquid crystal alignment treatment agent using the composition are a coating solution for forming a resin coating containing a specific solvent and a specific polysiloxane as a coating solution for forming a resin coating and a liquid crystal alignment layer (collectively referred to as a resin coating) .

All of the polymer components in the composition of the present invention and the liquid crystal alignment treatment agent may be the specific polysiloxane of the present invention or may be mixed with other polymers. Examples of the other polymer include acrylic polymer, methacrylic polymer, polystyrene, polyamic acid or polyimide. At that time, the content of the other polymer is 0.5 part by mass to 30 parts by mass with respect to 100 parts by mass of the specific polysiloxane of the present invention. Among them, 1 part by mass to 20 parts by mass is preferable.

The solvent in the composition of the present invention and the liquid crystal alignment treatment agent preferably has a solvent content of 70 to 99.9 mass% from the viewpoint of forming a uniform resin film by coating. This content can be appropriately changed depending on the intended thickness of the resin film and the application method.

As the solvent at this time, all may be the specific solvent of the present invention, but it may be used at the same time as a solvent (also referred to as another solvent) for dissolving the specific polysiloxane of the present invention. Specific examples of other solvents include, but are not limited to, the following examples.

Examples of the solvent include N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N- 1,3-dimethyl-imidazolidinone, methyl ethyl ketone, cyclohexanone, cyclopentanone, 4-hydroxy-4-methyl-2-pentanone, ethanol, isopropyl alcohol, Butanol, isobutanol, tert-butyl alcohol, 1-pentanol, 2-pentanol, Methyl-1-pentanol, 2-ethyl-1-butanol, 1-heptanol, 2-heptanol, 3-heptanol, But are not limited to, alcohols such as 1-octanol, 2-octanol, 2-ethyl-1-hexanol, cyclohexanol, 1-methylcyclohexanol, 2-methylcyclohexanol, , 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, 2 , 4-pentanediol, 2-ethyl-1,3-hexanediol, dipropyl ether, dibutyl ether, dihexyl ether, dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether , 2-butoxyethane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dibutyl ether, 2-pentanone, 3-pentanone, Ethylhexyl acetate, ethylene glycol monoacetate, ethylene glycol diacetate, propylene carbonate, ethylene carbonate, propylene carbonate, ethylene carbonate, propylene carbonate, (Methoxymethoxy) ethanol, ethylene glycol monobutyl ether, ethylene glycol monoisobutyl ether, ethylene glycol monohexyl ether, 2- (hexyloxy) ethanol, furfuryl alcohol, diethylene glycol, diethylene glycol Monoethyl ether, diethylene glycol monopropyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monobutyl ether, propylene glycol, propylene glycol monobutyl ether, 1- (butoxyethoxy) Propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, tripropylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, Diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, 2- (2-ethoxyethoxy) ethyl acetate, diethylene glycol acetate, diethylene glycol monoacetate, diethylene glycol monoacetate, Propylene glycol monomethyl ether, ethylene glycol, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, methyl acetate, ethyl acetate, n-butyl acetate, propylene glycol monoethyl ether acetate, methyl pyruvate, methyl pyruvate, Methoxypropionic acid, propyl 3-methoxypropionate, butyl 3-methoxypropionate, methyl lactate, ethyl lactate, n-propyl lactate, isopropyl myristate, isopropyl myristate, N-butyl lactate, and lactic acid isoam wheat.

Among them, N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone,? -Butyrolactone, 1,3-dimethyl-imidazolidinone, methyl ethyl ketone, cyclohexanone, cyclopenta Butanediol, 1,3-butanediol, 1,3-butanediol, 2,3-butanediol, 1,2-butanediol, Diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monopropyl ether, propylene glycol monomethyl ether , Propylene glycol monoethyl ether, propylene glycol monobutyl ether, dipropylene glycol monomethyl ether, dipropylene glycol dimethyl ether or furfuryl alcohol are preferable.

The other solvent of the present invention is preferably 10 to 90% by mass of the total solvent contained in the composition and the liquid crystal alignment treatment agent. Among these, 15 to 80 mass% is preferable. The more preferred range is 20 to 80 mass%, and the more preferable range is 30 to 70 mass%.

The other solvent of the present invention may be used alone or in combination of two or more, depending on the solubility of the specific polysiloxane of the present invention in the solvent, and the applicability of the composition and the liquid crystal alignment treatment agent.

The composition and the liquid crystal alignment treatment agent of the present invention may contain a crosslinkable compound having an epoxy group, an isocyanate group, an oxetane group or a cyclocarbonate group, a crosslinkable compound having at least one substituent selected from a hydroxyl group, a hydroxyalkyl group and a lower alkoxyalkyl group It is preferable to introduce a compound or a crosslinkable compound having a polymerizable unsaturated bond. These substituent groups and polymerizable unsaturated bonds need to have two or more in the crosslinkable compound.

Examples of the crosslinkable compound having an epoxy group or an isocyanate group include bisphenol acetone glycidyl ether, phenol novolac epoxy resin, cresol novolak epoxy resin, triglycidyl isocyanurate, tetraglycidyl amino diphenylene , Tetraglycidyl-m-xylenediamine, tetraglycidyl-1,3-bis (aminoethyl) cyclohexane, tetraphenyl glycidyl ether ethane, triphenyl glycidyl ether ethane, bisphenol hexafluoroacetate Diglycidyl ether, 1,3-bis (1- (2,3-epoxypropoxy) -1-trifluoromethyl-2,2,2-trifluoromethyl) benzene, 4,4-bis 2- (4- (2,3-epoxypropoxy) phenyl) -2- (4-methylpentanoyloxyphenyl) octafluorobiphenyl, triglycidyl-p-aminophenol, tetraglycidyl methadienyldiamine, 2- (4- (1, 4- (2,3-epoxypropoxy) phenyl) ethyl) phenyl) propane or 1,3- Oxy) phenyl) -1- ( 1-methylethyl) phenyl) ethyl) phenoxy) -2-propanol, and the like.

The crosslinkable compound having an oxetane group is a crosslinkable compound having at least two oxetane groups represented by the following formula [4A].

(31)

Specifically, there can be mentioned the crosslinkable compounds represented by the formulas [4a] to [4k] listed in 58 to 59 of International Publication No. 2011/132751 (published on October 27, 2011).

The crosslinkable compound having a cyclocarbonate group is a crosslinkable compound having at least two cyclocarbonate groups represented by the following formula [5A].

(32)

Specifically, there can be mentioned the crosslinkable compounds represented by the formulas [5-1] to [5-42] listed in the paragraphs 76 to 82 of International Publication No. 2012/014898 (published on February 22, 2012).

Examples of the crosslinkable compound having at least one substituent selected from the group consisting of a hydroxyl group and an alkoxyl group include an amino resin having a hydroxyl group or an alkoxyl group such as a melamine resin, Guanamine resin, glycoluril-formaldehyde resin, succinylamide-formaldehyde resin or ethylene urea-formaldehyde resin. Specifically, a melamine derivative in which the hydrogen atom of the amino group is substituted with a methylol group or an alkoxymethyl group, or a benzoguanamine derivative or glycoluril can be used. The melamine derivative or the benzoguanamine derivative may be present as a dimer or trimer. They preferably have 3 to 6, on average, methylol groups or alkoxymethyl groups per one triazine ring.

Examples of such a melamine derivative or benzoguanamine derivative include MX-750 in which an average of 3.7 methoxymethyl groups is substituted per one triazine ring of a commercial product, and methoxymethyl groups per one triazine ring are substituted on an average of 5.8 Methomethylated melamine such as MW-30 (manufactured by Sanwa Chemical Co., Ltd.) or Cymel 300, 301, 303, 350, 370, 771, 325, 327, 703 and 712, Cymel 235, 236, , 253, 254, methoxymethylated methoxymethylated melamines such as Cymel 506, 508, carboxyl-containing methoxymethylated isobutoxymethylated melamines such as Cymel 1141, methoxymethylated methoxymethylated isobutoxymethylated melamines such as Cymel 1123, Ethoxymethylated benzoguanamine, methoxymethylated butoxymethylated benzoguanamine such as Cymel 1123-10, butoxymethylated benzoguanamine such as Cymel 1128, carboxyl-containing methoxymethylated methoxymethylated methoxymethylated benzoguanamine such as Cymel 1125-80 Benzo Ana min can be given (or more, between the mid-Mitsui Ana Company). Examples of the glycoluril include butoxymethylated glycoluril such as Cymel 1170, methylol glycoluryl such as Cymel 1172, and methoxymethylolglycoluril such as Powderlink 1174 and the like.

Examples of the benzene or phenolic compound having a hydroxyl group or an alkoxyl group include 1,3,5-tris (methoxymethyl) benzene, 1,2,4-tris (isopropoxymethyl) benzene, 1 , 4-bis (sec-butoxymethyl) benzene, or 2,6-dihydroxymethyl-p-tert-butylphenol.

More specifically, there can be mentioned the crosslinkable compounds represented by the formulas [6-1] to [6-48], which are listed on pages 62 to 66 of International Publication No. 2011/132751 .

Examples of the crosslinkable compound having a polymerizable unsaturated bond include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, tri ) Acryloyloxyethoxy trimethylol propane or glycerin polyglycidyl ether poly (meth) acrylate, and also crosslinkable compounds having three polymerizable unsaturated groups in the molecule, such as ethylene glycol di (meth) acrylate, di Acrylates such as ethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, polypropylene glycol di Di (meth) acrylate, neopentyl glycol di (meth) acrylate, ethylene oxide bisphenol A type di (meth) acrylate, (Meth) acrylate, pentaerythritol di (meth) acrylate, ethylene glycol diglycidyl ether di (meth) acrylate, diethylene glycol di (Meth) acrylate, diethylene glycol diglycidyl ether di (meth) acrylate, phthalic acid diglycidyl ester di (meth) acrylate or hydroxypivalic neopentyl glycol di (Meth) acrylate, 2-hydroxybutyl (meth) acrylate, 2-phenoxy (meth) acrylate, 2-hydroxyethyl 2-hydroxypropyl (meth) acrylate, glycerin mono (meth) acrylate, 2- (meth) acryloyloxy- Acrylate, 2- ( Agent) and a polymerizable unsaturated group such as acryloyloxyethyl phosphate ester or N- methylol (meth) acrylamide and the like crosslinkable compound having in the molecule one.

In addition, a compound represented by the following formula [7A] may be used.

(33)

(Wherein E ¹ represents at least one member selected from a cyclohexane ring, a bicyclohexane ring, a benzene ring, a biphenyl ring, a terphenyl ring, a naphthalene ring, a fluorene ring, an anthracene ring and a phenanthrene ring) And E ² represents a group selected from the following formula [7a] or formula [7b], and n represents an integer of 1 to 4.)

(34)

The compound is an example of a crosslinking compound, but is not limited thereto. The crosslinking compound used in the composition of the present invention and the liquid crystal alignment treatment agent may be one kind or two or more kinds.

The content of the crosslinkable compound in the composition of the present invention and the liquid crystal alignment treatment agent is preferably 0.1 part by mass to 150 parts by mass with respect to 100 parts by mass of all the polymer components. Among them, 0.1 part by mass to 100 parts by mass is preferable for 100 parts by mass of all the polymer components in order for the crosslinking reaction to proceed and to exhibit the intended effect. More preferred is 1 part by mass to 50 parts by mass.

The composition and the liquid crystal alignment treatment agent of the present invention may use a compound which improves the uniformity of the film thickness of the resin film and the surface smoothness when the composition and the liquid crystal alignment treatment agent are applied thereto as long as the effect of the present invention is not impaired.

Examples of the compound that improves the film thickness uniformity and surface smoothness of the resin film include a fluorine-based surfactant, a silicon-based surfactant, and a nonionic surface-active agent.

More specifically, for example, EF301, EF303 and EF352 (manufactured by TOKEM PRODUCTS CO., LTD.), Megafac F171, F173 and R-30 (manufactured by Dainippon Ink and Chemicals Inc.), Fluorad FC430 and FC431 SC103, SC104, SC105, and SC106 (manufactured by Asahi Glass Co., Ltd.)), and the like.

The use ratio of these surfactants is preferably 0.01 parts by mass to 2 parts by mass, more preferably 0.01 parts by mass to 1 part by mass, relative to 100 parts by mass of all the polymer components contained in the composition and the liquid crystal alignment treatment agent.

The composition of the present invention and the liquid crystal alignment treatment agent are compounds which accelerate the charge transfer in the resin film to promote the omission of charge of the device and are disclosed in, for example, International Patent Publication No. 2011/132751 (published on October 22, 2011) A nitrogen-containing heterocyclic amine compound represented by the formula [M1] to formula [M156] may be added. The amine compound may be added directly to the composition and the liquid crystal alignment treatment agent, but it is preferable to add the amine compound in a suitable solvent at a concentration of 0.1% by mass to 10% by mass, preferably 1% by mass to 7% by mass. This solvent is not particularly limited as long as it is a solvent for dissolving the above-mentioned specific polysiloxane.

The composition and the liquid crystal alignment treatment agent of the present invention may contain, in addition to the above-mentioned other compounds for improving the uniformity of the film thickness of the solvent, the crosslinking compound, and the resin film and the surface smoothness, A dielectric material or a conductive material may be added for the purpose of changing electric characteristics such as dielectric constant and conductivity of the resin film.

&Lt; Resin Coating &gt;

The composition of the present invention can be used as a resin film after being coated and baked on a substrate. As the substrate to be used in this case, a plastic substrate such as a glass substrate, a silicon wafer, an acrylic substrate, a polycarbonate substrate, or a PET (polyethylene terephthalate) substrate may be used depending on the intended device. Further, the resin film can be used as it is as a film substrate. The method of applying the composition is not particularly limited, but a method of industrially performing the method by dip coating, roll coating, slit coating, spinner coating, spray coating, screen printing, offset printing, It is common. They may be used according to the purpose.

After the composition is applied onto the substrate, it is heated at 30 to 300 占 폚, preferably 30 to 250 占 폚, depending on the solvent used for the composition, by a heating means such as a hot plate, a heat circulation type oven or an IR Lt; RTI ID = 0.0 &gt; C, &lt; / RTI &gt; The thickness of the resin film after firing can be adjusted to 0.01 to 100 탆, depending on the purpose.

<Liquid Crystal Alignment Film / Liquid Crystal Display Device>

The liquid crystal alignment treatment agent using the composition of the present invention can be used as a liquid crystal alignment film after being applied and baked on a substrate and subjected to an orientation treatment by rubbing treatment, light irradiation, or the like. Further, a liquid crystal display element in which a liquid crystal is vertically aligned to perform display can be used as a liquid crystal alignment film without alignment treatment. The substrate to be used at this time is not particularly limited as long as it is a substrate having high transparency. In addition to the glass substrate, a plastic substrate such as an acrylic substrate, a polycarbonate substrate, or a PET (polyethylene terephthalate) substrate can also be used. From the viewpoint of simplifying the process, it is preferable to use a substrate on which an ITO (indium tin oxide) electrode for liquid crystal driving is formed. Further, in a reflective liquid crystal display device, an opaque substrate such as a silicon wafer can be used only for a substrate on one side, and as the electrode in this case, a material for reflecting light such as aluminum can also be used.

The method of applying the liquid crystal alignment treatment agent is not particularly limited, but industrially, a method of screen printing, offset printing, flexographic printing, or inkjet printing is generally used. Other coating methods include a dipping method, a roll coater method, a slit coater method, a spinner method, and a spraying method, and they may be used depending on the purpose.

After the liquid crystal alignment treatment agent is applied onto the substrate, it is heated to 30 to 300 占 폚, preferably 30 to 300 占 폚, depending on the solvent used for the liquid crystal alignment treatment agent by a heating means such as a hot plate, a heat- The liquid crystal alignment layer can be formed by evaporating the solvent at a temperature of 30 to 250 ° C. When the thickness of the liquid crystal alignment film after firing is too large, the power consumption of the liquid crystal display element is disadvantageously deteriorated. When the thickness is too thin, the reliability of the liquid crystal display element may deteriorate. Therefore, the thickness is preferably 5 to 300 nm, Is 10 to 150 nm. When the liquid crystal is horizontally or tilted, the fired liquid crystal alignment film is treated by rubbing, polarized ultraviolet irradiation, or the like.

In the liquid crystal display element of the present invention, a substrate on which a liquid crystal alignment film is formed from the liquid crystal alignment treatment agent of the present invention is obtained by the above technique, and then a liquid crystal cell is produced by a known method to form a liquid crystal display element.

As a manufacturing method of a liquid crystal cell, a pair of substrates on which a liquid crystal alignment film is formed is prepared, spacers are dispersed on a liquid crystal alignment film of a substrate of one substrate, the substrates of the other substrate are laminated so that the liquid crystal alignment film surface is inward, A method in which a liquid crystal is injected under reduced pressure and a method in which liquid crystal is dropped on the surface of a liquid crystal alignment film on which a spacer is dispersed and a method in which a substrate is bonded by sticking is exemplified.

The liquid crystal alignment treatment agent of the present invention is a liquid crystal alignment treatment agent comprising a liquid crystal layer between a pair of substrates provided with an electrode and containing a polymerizable compound polymerized by at least one of active energy rays and heat between a pair of substrates The present invention is preferably used for a liquid crystal display device produced by a process of arranging a liquid crystal composition and polymerizing a polymerizable compound by at least one of irradiation of an active energy ray and heating while applying a voltage between electrodes. Here, as the active energy ray, ultraviolet ray is preferable. The ultraviolet ray has a wavelength of 300 to 400 nm, preferably 310 to 360 nm. In the case of polymerization by heating, the heating temperature is 40 to 120 占 폚, preferably 60 to 80 占 폚. In addition, ultraviolet rays and heating may be simultaneously performed.

The liquid crystal display element described above controls the pretilt of liquid crystal molecules by a PSA (Polymer Sustained Alignment) method. In the PSA system, a small amount of a photopolymerizable compound such as a photopolymerizable monomer is mixed into a liquid crystal material, and a liquid crystal cell is assembled. Then, a predetermined voltage is applied to the liquid crystal layer, And controls the pretilt of the liquid crystal molecules by the produced polymer. Since the alignment state of the liquid crystal molecules when the polymer is produced is stored even after the voltage is removed, the pretilt of the liquid crystal molecules can be adjusted by controlling the electric field or the like formed on the liquid crystal layer. Further, in the PSA system, since the rubbing treatment is not required, it is suitable for forming a vertical alignment type liquid crystal layer which is difficult to control the pretilt by the rubbing treatment.

That is, the liquid crystal display element of the present invention can be obtained by obtaining a substrate on which a liquid crystal alignment film is formed from the liquid crystal alignment treatment agent of the present invention by the above-mentioned technique, preparing a liquid crystal cell, And the orientation of the liquid crystal molecules can be controlled by polymerization.

For example, a pair of substrates on which a liquid crystal alignment film is formed is prepared, a spacer is dispersed on the liquid crystal alignment film of the substrate of the single chamber, and the liquid crystal alignment film surface is made inward, A method in which a liquid crystal is injected under reduced pressure and sealed, or a method in which a liquid crystal is dropped on a surface of a liquid crystal alignment film on which a spacer is dispersed, and then a substrate is bonded and sealed.

The liquid crystal is mixed with a polymerizable compound which is polymerized by irradiation with heat or ultraviolet rays. Examples of the polymerizable compound include a compound having at least one polymerizable unsaturated group such as an acrylate group or a methacrylate group in the molecule. At that time, the polymerizable compound is preferably 0.01 to 10 parts by mass, more preferably 0.1 to 5 parts by mass, per 100 parts by mass of the liquid crystal component. If the amount of the polymerizable compound is less than 0.01 part by mass, the polymerization of the polymerizable compound is not polymerized, and the alignment control of the liquid crystal becomes impossible. If more than 10 parts by mass, the unreacted polymerizable compound increases and the baking property of the liquid crystal display element deteriorates .

After the liquid crystal cell is manufactured, the polymerizable compound is polymerized by applying heat or ultraviolet rays while applying alternating current or direct current voltage to the liquid crystal cell. Thereby, the orientation of the liquid crystal molecules can be controlled.

In addition, the liquid crystal alignment treatment agent of the present invention includes a liquid crystal layer between a pair of substrates provided with electrodes, and includes a polymerizable group which polymerizes by at least one of active energy rays and heat between the pair of substrates It is preferably used for a liquid crystal display element manufactured by arranging a liquid crystal alignment film and applying a voltage between electrodes. Here, as the active energy ray, ultraviolet ray is preferable. The ultraviolet ray has a wavelength of 300 to 400 nm, preferably 310 to 360 nm. In the case of polymerization by heating, the heating temperature is 40 to 120 占 폚, preferably 60 to 80 占 폚. In addition, ultraviolet rays and heating may be simultaneously performed.

In order to obtain a liquid crystal alignment film containing a polymerizable group polymerizing from at least one of the active energy ray and heat, a method of adding a compound containing the polymerizable group to the liquid crystal alignment treatment agent or a method of using a polymer component containing a polymerizable group . Since the liquid crystal alignment treatment agent of the present invention contains a specific compound having a double bonding site that reacts by irradiation with heat or ultraviolet rays, the orientation of the liquid crystal molecules can be controlled by at least one of irradiation of ultraviolet rays and heating have.

For example, a pair of substrates on which a liquid crystal alignment film is formed is prepared, a spacer is dispersed on the liquid crystal alignment film of the substrate of the single chamber, A method in which a liquid crystal is injected under reduced pressure and a method in which a liquid crystal is dropped on the surface of a liquid crystal alignment film on which a spacer is dispersed and the substrate is then subjected to sealing by bonding.

After the liquid crystal cell is fabricated, the alignment of the liquid crystal molecules can be controlled by applying heat or ultraviolet rays while applying alternating current or direct current voltage to the liquid crystal cell.

As described above, the liquid crystal alignment treatment agent of the present invention becomes a liquid crystal alignment film having excellent film properties, and further, a liquid crystal alignment film capable of exhibiting a stable pretilt angle even after exposure to high temperature and light irradiation for a long time. Therefore, the liquid crystal display element having the liquid crystal alignment film obtained from the liquid crystal alignment treatment agent of the present invention is excellent in reliability, and can be suitably used for a large-screen liquid crystal television, a medium-sized car navigation system, or a smart phone.

Example

Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited thereto.

&Quot; Abbreviations used in Synthesis Examples, Examples and Comparative Examples of the Present Invention &quot;

Abbreviations used in Synthesis Examples, Examples and Comparative Examples are as follows.

&Lt; Monomer for producing the polysiloxane polymer of the present invention &gt;

B1: an alkoxysilane monomer represented by the following formula [B1] (an alkoxysilane monomer represented by the formula [2a] having a specific side chain structure represented by the formula [2a-1]

B2: octadecyltriethoxysilane (alkoxysilane monomer represented by the formula [2a] having a specific side chain structure represented by the formula [2a-2] of the present invention)

B3: 3-methacryloxypropyltrimethoxysilane (alkoxysilane monomer represented by the formula [2b] of the present invention)

B4: 3-ureidopropyltriethoxysilane (alkoxysilane monomer represented by the formula [2b] of the present invention)

B5: tetraethoxysilane (alkoxysilane monomer represented by the formula [2c] of the present invention)

(35)

&Lt; Crosslinkable compound used in the present invention &gt;

K1: a crosslinkable compound represented by the following formula [K1]

(36)

&Lt; Specific solvent of the present invention &

S1: a solvent represented by the following formula [S1] (a solvent represented by the formula [1a] of the present invention)

(37)

<Other solvent>

EC: diethylene glycol monoethyl ether

BCS: ethylene glycol monobutyl ether

PB: Propylene glycol monobutyl ether

DME: dipropylene glycol dimethyl ether

NMP: N-methyl-2-pyrrolidone

NEP: N-ethyl-2-pyrrolidone

? -BL:? -butyrolactone

&Quot; Synthesis of polysiloxane polymer of the present invention &quot;

&Lt; Synthesis Example 1 &

A solution of alkoxysilane monomer was prepared by mixing EC (29.8 g), B1 (4.10 g) and B5 (39.6 g) in a 200 ml four-neck reaction flask equipped with a thermometer and reflux tube. A solution prepared by previously mixing EC (14.9 g), water (10.8 g) and oxalic acid (0.90 g) as a catalyst was added dropwise to this solution at 25 占 폚 over 30 minutes and further stirred at 25 占 폚 for 30 minutes at room temperature Respectively. Then, after heated using an oil bath reflux for 60 minutes, to obtain a polysiloxane solution bangraeng (1) SiO ₂ in terms of a concentration of 12% by mass.

&Lt; Synthesis Example 2 &

A solution of alkoxysilane monomer was prepared by mixing EC (29.7 g), B2 (4.20 g) and B5 (39.6 g) in a 200 ml four-neck reaction flask equipped with a thermometer and reflux tube. A solution prepared by previously mixing EC (14.9 g), water (10.8 g) and oxalic acid (0.90 g) as a catalyst was added dropwise to this solution at 25 占 폚 over 30 minutes and further stirred at 25 占 폚 for 30 minutes at room temperature Respectively. Then, after heated using an oil bath reflux for 60 minutes, bangraeng to obtain a polysiloxane solution (2) in terms of SiO ₂ concentration of 12% by mass.

&Lt; Synthesis Example 3 &

EC (28.2 g), B1 (4.10 g), B3 (14.9 g) and B5 (27.1 g) were mixed in a 200 ml four-neck reaction flask equipped with a stirrer, thermometer and reflux tube to give a solution of the alkoxysilane monomer Lt; / RTI &gt; To this solution, a solution prepared by previously mixing EC (14.1 g), water (10.8 g) and oxalic acid (0.90 g) as a catalyst was added dropwise at 25 占 폚 over 30 minutes and further stirred at 25 占 폚 for 30 minutes Lt; / RTI &gt; Then, after heated using an oil bath reflux for 60 minutes, bangraeng to give polysiloxane solution (3) in terms of SiO ₂ concentration of 12% by mass.

&Lt; Synthesis Example 4 &

(28.1 g), B2 (4.20 g), B3 (14.9 g) and B5 (27.1 g) were mixed in a 200 ml four-neck reaction flask equipped with a stirrer, thermometer and reflux tube to give a solution of the alkoxysilane monomer Lt; / RTI &gt; To this solution, a solution prepared by previously mixing S1.1 (14.1 g), water (10.8 g) and oxalic acid (0.90 g) as a catalyst was added dropwise at 25 DEG C over 30 minutes, and further added at 25 DEG C for 30 minutes Lt; / RTI &gt; Then, after heated using an oil bath reflux for 60 minutes, bangraeng to obtain a polysiloxane solution (4) in terms of SiO ₂ concentration of 12% by mass.

&Lt; Synthesis Example 5 &

(27.4 g), B1 (4.10 g), B3 (14.9 g) and B5 (26.3 g) were mixed in a 200 ml four-neck reaction flask equipped with a reflux condenser, thermometer and reflux tube to give a solution of the alkoxysilane monomer Respectively. To this solution, a solution prepared by previously mixing EC (13.7 g), water (10.8 g) and oxalic acid (0.90 g) as a catalyst was added dropwise at 25 占 폚 over 30 minutes and further stirred at 25 占 폚 for 30 minutes Lt; / RTI &gt; Thereafter, the mixture was heated using an oil bath and refluxed for 30 minutes, and then a mixed solution of a methanol solution (1.15 g) having a B4 content of 92% by mass previously adjusted and EC (0.90 g) was added. After additional 30 minutes at reflux, bangraeng to obtain a polysiloxane solution (5) in terms of SiO ₂ concentration of 12% by mass.

&Lt; Synthesis Example 6 &

A solution of alkoxysilane monomer was prepared by mixing EC (29.5 g), B3 (14.9 g) and B5 (29.2 g) in a 200 ml four-necked flask equipped with a thermometer and reflux tube. To this solution, a solution prepared by previously mixing EC (14.7 g), water (10.8 g) and oxalic acid (0.90 g) as a catalyst was added dropwise at 25 占 폚 over 30 minutes and further stirred at 25 占 폚 for 30 minutes Lt; / RTI &gt; Then, after heated using an oil bath reflux for 60 minutes, bangraeng to give polysiloxane solution (6) in terms of SiO ₂ concentration of 12% by mass.

&Lt; Synthesis Example 7 &

(30.3 g) and B5 (40.8 g) were mixed in a 200 ml four-neck reaction flask equipped with a stirrer, thermometer and reflux tube to adjust the solution of the alkoxysilane monomer. To this solution, a solution prepared by previously mixing S1 (15.2 g), water (10.8 g) and oxalic acid (0.90 g) as a catalyst was added dropwise at 25 占 폚 over 30 minutes and further stirred at 25 占 폚 for 30 minutes Lt; / RTI &gt; Thereafter, the mixture was heated using an oil bath and refluxed for 30 minutes, and then a mixed solution of methanol solution (1.15 g) and Si (0.90 g) having a B4 content of 92 mass% adjusted in advance was added. After additional 30 minutes at reflux, bangraeng to give polysiloxane solution (7) in terms of SiO ₂ concentration of 12% by mass.

&Lt; Synthesis Example 8 &

A solution of alkoxysilane monomer was prepared by mixing EC (28.7 g), B3 (14.9 g) and B5 (28.3 g) in a 200 ml four-necked flask equipped with a thermometer and reflux tube. To this solution, a solution prepared by previously mixing EC (14.4 g), water (10.8 g) and oxalic acid (0.90 g) as a catalyst was added dropwise at 25 占 폚 over 30 minutes and further stirred at 25 占 폚 for 30 minutes Lt; / RTI &gt; Thereafter, the mixture was heated using an oil bath and refluxed for 30 minutes, and then a mixed solution of a methanol solution (1.15 g) having a B4 content of 92% by mass previously adjusted and EC (0.90 g) was added. After additional 30 minutes at reflux, bangraeng to give polysiloxane solution (8) in terms of SiO ₂ concentration of 12% by mass.

Table 1 shows the polysiloxane (polysiloxane solution) of the present invention.

&Quot; Composition of the present invention and production of liquid crystal alignment treatment agent &quot;

In the following Examples 1 to 13 and Comparative Examples 1 to 3, production examples of compositions are described. These compositions are also used for evaluation of the liquid crystal alignment treatment agent.

The composition of the present invention and the liquid crystal alignment treatment agent are shown in Tables 2 to 4.

Evaluation of printability of composition and liquid crystal alignment treatment agent (evaluation of pinhole) &quot;, &quot; evaluation of printability of composition and liquid crystal alignment treatment agent &quot; Evaluation of inkjet application property of liquid crystal alignment treatment agent &quot;, &quot; Preparation of liquid crystal cell and evaluation of liquid crystal alignment property (PSA cell) &quot;, and &quot; (SC-PVA cell) &quot;.

&Quot; Evaluation of printability of composition and liquid crystal alignment treatment agent (evaluation of pinhole) &quot;

The pinholes of the resin coatings were evaluated using the compositions obtained by the methods of Examples and Comparative Examples of the present invention. Specifically, these compositions were pressure-filtered with a membrane filter having a pore diameter of 1 占 퐉 to perform printing on a fine-definition Cr deposited substrate (100 mm long × 100 mm wide and 1.0 mm thick). In the printing machine, a printing machine S15 type (manufactured by Nihon Photo Printing Co., Ltd.) was used, and the printing area was in the range of 80 x 80 mm with respect to the center of the substrate, the pressure was 0.2 mm, ) The drying time was 90 seconds and drying was carried out on a hot plate at 70 DEG C for 5 minutes.

Thereafter, the number of pinholes of the obtained substrate on which the resin coating was formed was confirmed. Specifically, the substrate on which the resin coating was formed was observed with naked eyes under a sodium lamp, and the number of pinholes on the resin coating was counted. Further, the smaller the number of pinholes, the smaller the number of precipitates in the composition and the better the evaluation was made.

Tables 5 to 7 show the number of pin holes obtained in Examples and Comparative Examples.

In addition, the compositions obtained in Examples and Comparative Examples of the present invention can be used for a liquid crystal alignment treatment agent. Therefore, the evaluation of the pinhole of the resin coating of the composition obtained in Examples and Comparative Examples of the present invention was also called evaluation of pinhole of the liquid crystal alignment film.

&Quot; Evaluation of printability of composition and liquid crystal alignment treatment agent (Evaluation of stepwise followability) &quot;

Using the compositions obtained by the methods of Examples and Comparative Examples of the present invention, evaluation of the printability of the stepped substrate of the resin coating was carried out. Specifically, these compositions were pressure-filtered through a membrane filter having a pore diameter of 1 占 퐉, and a 100 占 퐉 100 占 퐉 dot pattern (50 占 퐉 dot-to-dot spacing, 0.5 (100 mm in length x 100 mm in width and 0.7 mm in thickness) to which a glass substrate having a thickness of 100 mu m was applied. In the printing machine, a printing machine S15 type (manufactured by Nihon Photo Printing Co., Ltd.) was used, and the printing area was in the range of 80 x 80 mm relative to the center of the substrate, 0.2 mm in pressure, 5 sheets of scrapers, Was carried out on a hot plate at 70 DEG C for 5 minutes.

The resin film thus obtained was evaluated for the followability of the resin film to the stepped substrate. Specifically, the cross-section of the obtained substrate with the resin coating film was observed with a scanning electron microscope (S-4800) (manufactured by Hitachi High-Technologies Corporation), and the film thickness of the resin coating on the dot top and the film thickness of the resin coating between the dots were checked . More specifically, the film thickness (the film thickness of the resin film at the upper portion of the dot and the film thickness of the resin film between the dots) of (1) in Fig. 1 (the film thickness at the center of the dot) The film thickness of the central portion between the dots) was confirmed, and the smaller the difference, the better the followability of the resin film to the stepped substrate.

Tables 5 to 7 show the film thicknesses of (1), (2) and (2) (((1) / (2)) obtained in Examples and Comparative Examples ) X 100).

In addition, the compositions obtained in Examples and Comparative Examples of the present invention can be used for a liquid crystal alignment treatment agent. For this reason, evaluation of the stepwise followability of the composition obtained in the examples and comparative examples of the present invention was also evaluated as to the stepwise followability of the liquid crystal alignment film.

&Quot; Fabrication of liquid crystal cell and evaluation of pretilt angle (normal cell) &quot;

Using the liquid crystal alignment treatment agents obtained by the methods of Examples and Comparative Examples of the present invention, the production of a liquid crystal cell and the evaluation of the pretilt angle were carried out. Specifically, these liquid crystal alignment treatment agents were pressure-filtered with a membrane filter having a pore diameter of 1 占 퐉 and cleaned with pure water and IPA (isopropyl alcohol), on which substrates (40 mm long × 30 mm wide and 0.7 mm thick ), And subjected to heat treatment on a hot plate at 80 DEG C for 5 minutes and at 220 DEG C for 30 minutes in a thermocycling type clean oven to obtain an ITO substrate on which a polyimide liquid crystal alignment film having a thickness of 100 nm was formed. The coated surface of the ITO substrate was subjected to rubbing under the conditions of a roll rotation number of 1000 rpm, a roll advancing speed of 50 mm / sec, and a pressing amount of 0.1 mm using a rayon cloth with a rubbing apparatus having a roll diameter of 120 mm.

Two sheets of the ITO substrates on which the liquid crystal alignment film was formed were prepared, and the liquid crystal alignment film surface was set inside with the spacers of 6 mu m interposed therebetween, and the periphery was bonded with a sealant to prepare empty cells. A nematic liquid crystal (MLC-6608) (manufactured by Merck Japan Co., Ltd.) was injected into the empty cell by a vacuum injection method and the injection port was sealed to obtain a liquid crystal cell (ordinary cell).

The obtained liquid crystal cell was used to evaluate the pretilt angle. The pretilt angle is measured after the isotropic treatment at 95 캜 for 5 minutes (immediately after the production of the liquid crystal cell), after the liquid crystal injection, after the heat treatment at 120 캜 for 5 hours (also referred to as high temperature storage) C for 5 minutes was irradiated with ultraviolet rays of 10 J / cm 2 in terms of 365 nm (also referred to as ultraviolet ray irradiation) in a liquid crystal cell.

The pretilt angle was measured at room temperature using PAS-301 (manufactured by ELSICON). The irradiation with ultraviolet rays was carried out using a table-top UV curing device (HCT3B28HEX-1) (manufactured by Sen Wright).

The evaluation was performed such that the smaller the change in the pretilt angle after storage of the high-temperature bath or after the irradiation with ultraviolet rays, the better the stability of the pretilt angle with respect to heat and ultraviolet ray, relative to the pretilt angle immediately after the production of the liquid crystal cell.

Table 8 and Table 9 show the values of the pretilt angles obtained in Examples and Comparative Examples.

Evaluation of inkjet application property of liquid crystal alignment treatment agent &quot;

Using the liquid crystal alignment treatment agent (4) obtained by the method of Example 4 of the present invention, the liquid crystal alignment treatment agent (7) obtained by the method of Example 7 and the liquid crystal alignment treatment agent (10) obtained by the method of Example 10, The evaluation of sexuality was carried out. Specifically, these liquid crystal alignment treatment agents were pressure-filtered with a membrane filter having a pore diameter of 1 占 퐉, and then cleaned with pure water and IPA using an HIS-200 (Hitachi Plant Technology Co., Ltd.) , The nozzle pitch was 0.423 mm, the scan pitch was 0.5 mm, the coating speed was 40 mm / sec, the time from coating to drying was 60 seconds, and drying was carried out on a hot plate at 70 占 폚 The coating was carried out under the condition of 5 minutes.

The obtained substrate on which the liquid crystal alignment film was formed was observed with naked eyes under a sodium lamp to count the number of pinholes on the liquid crystal alignment film. As a result, all of the liquid crystal alignment films obtained in all Examples had pin holes of 5 or less. Further, in all of the examples, a liquid crystal alignment film excellent in coat film uniformity was obtained.

Using the substrate on which the obtained liquid crystal alignment film was formed, the liquid crystal cell was produced and the evaluation of the pretilt angle (normal cell) was carried out under the conditions of "preparation of liquid crystal cell and evaluation of pretilt angle (normal cell)" .

&Quot; Production of liquid crystal cell and evaluation of liquid crystal orientation property (PSA cell) &quot;

Production of a liquid crystal cell and evaluation of liquid crystal orientation (PSA cell) were carried out using the liquid crystal alignment treatment agent 3 obtained in the method of Example 3 of the present invention and the liquid crystal alignment treatment agent 6 obtained by the method of Example 6 . Specifically, these liquid crystal alignment treatment agents were pressure-filtered with a membrane filter having a pore diameter of 1 占 퐉, cleaned with pure water and IPA, and transferred to a substrate having an ITO electrode having a pattern interval of 20 占 퐉 of 10 占 10 mm 30 mm in length and 0.7 mm in thickness) and ITO surface of a substrate (40 mm long x 30 mm wide and 0.7 mm thick) on which ITO electrodes of 10 x 40 mm were formed at the center were spin-coated on a hot plate at 100 DEG C for 5 minutes, The substrate was subjected to a heat treatment at 230 캜 for 30 minutes in a thermocycling type clean oven to obtain a substrate on which a liquid crystal alignment film having a thickness of 100 nm was formed.

The substrates on which these liquid crystal alignment films were formed were assembled with spacers having a size of 6 mu m interposed therebetween with the liquid crystal alignment film surface on the inner side and bonded to the periphery with a sealant to prepare blank cells. The polymerizable compound (1) represented by the following formula was dissolved in 100 ml of a nematic liquid crystal (MLC-6608) (manufactured by Merck Japan Co., Ltd.) A liquid crystal mixed with 0.3% by mass of the polymerizable compound (1) relative to the mass% was injected, and the injection port was sealed to obtain a liquid crystal cell.

(38)

A wavelength of 350 nm or less was cut using a metal halide lamp having an illuminance of 60 mW while applying an AC voltage of 5 V to the obtained liquid crystal cell and irradiated with ultraviolet light of 20 J / cm 2 in terms of 365 nm, (PSA cell) in which the alignment direction of the liquid crystal cell was controlled. The temperature in the irradiator when the liquid crystal cell was irradiated with ultraviolet rays was 50 占 폚.

The response speeds of the liquid crystal cell before and after ultraviolet irradiation were measured. The response speed was measured from T90 to T10 from a transmittance of 90% to a transmittance of 10%.

It was confirmed that the PSA cell obtained in any of the Examples controlled the alignment direction of the liquid crystal in that the response speed of the liquid crystal cell after ultraviolet ray irradiation was faster than that of the liquid crystal cell before the ultraviolet ray irradiation. All liquid crystal cells were observed with a polarizing microscope (ECLIPSE E600WPOL) (Nikon Corporation), and it was confirmed that the liquid crystal was uniformly oriented.

&Quot; Production of liquid crystal cell and evaluation of liquid crystal alignment property (SC-PVA cell) &quot;

(SC-PVA cell) was evaluated using the liquid crystal alignment treatment agent (3) obtained by the method of Example 3 of the present invention and the liquid crystal alignment treatment agent (6) obtained by the method of Example 6 Respectively. Specifically, the above-mentioned polymerizable compound (1) was added to these liquid crystal alignment treatment agents in an amount of 2% by mass based on 100% by mass of the whole polymer component in the liquid crystal alignment treatment agent, and the mixture was stirred at 25 캜 for 4 hours. Thereafter, the resultant liquid crystal alignment treatment agent was pressure-filtered with a membrane filter having a pore diameter of 1 占 퐉 and cleaned with pure water and IPA to obtain a substrate (40 mm in length x 30 mm in width) having an ITO electrode with a 10- (Length: 40 mm, width: 30 mm, thickness: 0.7 mm) on which ITO electrodes having a size of 10 mm x 40 mm were formed, and the substrate was spin-coated on a hot plate at 100 DEG C for 5 minutes, The substrate was heated in a circulating type clean oven at 200 DEG C for 30 minutes to obtain a substrate on which a liquid crystal alignment film having a thickness of 100 nm was formed.

The substrates on which these liquid crystal alignment films were formed were assembled with spacers having a size of 6 mu m interposed therebetween with the liquid crystal alignment film surface on the inner side and bonded to the periphery with a sealant to prepare blank cells. A nematic liquid crystal (MLC-6608) (manufactured by Merck Japan Co.) was injected into the empty cell by a vacuum injection method and the injection port was sealed to obtain a liquid crystal cell.

A wavelength of 350 nm or less was cut using a metal halide lamp having an illuminance of 60 mW while applying an AC voltage of 5 V to the obtained liquid crystal cell and irradiated with ultraviolet light of 20 J / cm 2 in terms of 365 nm, (SC-PVA cell) in which the alignment direction of the liquid crystal cell was controlled. The temperature in the irradiator when the liquid crystal cell was irradiated with ultraviolet rays was 50 占 폚.

The response speeds of the liquid crystal cell before and after ultraviolet irradiation were measured. The response speed was measured from T90 to T10 from a transmittance of 90% to a transmittance of 10%.

The SC-PVA cell obtained in any of the Examples was confirmed to have the liquid crystal cell alignment direction controlled in that the response speed of the liquid crystal cell after ultraviolet ray irradiation was faster than that of the liquid crystal cell before the ultraviolet ray irradiation. All liquid crystal cells were observed with a polarizing microscope (ECLIPSE E600WPOL) (Nikon Corporation), and it was confirmed that the liquid crystal was uniformly oriented.

&Lt; Example 1 &gt;

EC (0.90 g), S1 (8.46 g) and BCS (5.64 g) were added to the polysiloxane solution (1) (15.0 g) obtained by the procedure of Synthesis Example 1 and stirred at 25 占 폚 for 3 hours to obtain a composition ). No abnormality such as turbidity or generation of precipitates was observed in this composition, and it was confirmed that the solution was a homogeneous solution. This composition (1) was also used for evaluation as the liquid crystal alignment treatment agent (1).

Evaluation of printability of composition and liquid crystal alignment treatment agent (evaluation of pinhole), evaluation of printability of composition and liquid crystal alignment treatment agent (evaluation of stepwise followability) &quot;, &quot; And &quot; preparation of liquid crystal cell and evaluation of pretilt angle (normal cell) &quot;.

&Lt; Example 2 &gt;

EC (0.90 g), S1 (8.46 g) and PB (5.64 g) were added to the polysiloxane solution 2 (15.0 g) obtained by the procedure of Synthetic Example 2 and stirred at 25 占 폚 for 3 hours to obtain a composition 2 ). No abnormality such as turbidity or generation of precipitates was observed in this composition, and it was confirmed that the solution was a homogeneous solution. The composition (2) was also used for the evaluation as the liquid crystal alignment treatment agent (2).

Evaluation of printability of composition and liquid crystal alignment treatment agent (evaluation of pinhole), evaluation of printability of composition and liquid crystal alignment treatment agent (evaluation of stepwise followability) &quot;, &quot; And &quot; preparation of liquid crystal cell and evaluation of pretilt angle (normal cell) &quot;.

&Lt; Example 3 &gt;

EC (0.93 g), S1 (11.7 g) and PB (2.91 g) were added to the polysiloxane solution 3 (15.5 g) obtained by the procedure of Synthesis Example 3 and stirred at 25 占 폚 for 3 hours to obtain a composition ). No abnormality such as turbidity or generation of precipitates was observed in this composition, and it was confirmed that the solution was a homogeneous solution. The composition (3) was also used for evaluation as the liquid crystal alignment treatment agent (3).

Evaluation of printability of composition and liquid crystal alignment treatment agent (evaluation of pinhole), evaluation of printability of composition and liquid crystal alignment treatment agent (evaluation of stepwise followability) &quot; (Production of Liquid Crystal Cell and Evaluation of Pretilt Angle (Normal Cell)), Production of Liquid Crystal Cell and Evaluation of Liquid Crystal Orientation (PSA Cell), Production of Liquid Crystal Cell and Evaluation of Liquid Crystal Orientation (SC-PVA Cell) Was carried out.

<Example 4>

EC (7.74 g), S1 (9.93 g), PB (3.31 g) and? -BL (3.31 g) were added to the polysiloxane solution 3 (10.0 g) obtained by the procedure of Synthetic Example 3, Followed by stirring for 3 hours to obtain a composition (4). No abnormality such as turbidity or generation of precipitates was observed in this composition, and it was confirmed that the solution was a homogeneous solution. The composition (4) was used for evaluation as the liquid crystal alignment treatment agent (4).

Evaluation of inkjet application property of liquid crystal alignment treatment agent &quot;, &quot; production of liquid crystal cell and evaluation of pretilt angle (normal cell) &quot; were performed using the obtained liquid crystal alignment treatment agent (4).

&Lt; Example 5 &gt;

S1 (3.72 g), BCS (8.46 g) and NMP (2.82 g) were added to the polysiloxane solution 4 (15.0 g) obtained by the procedure of Synthetic Example 4 and stirred at 25 占 폚 for 3 hours to obtain a composition 5 ). No abnormality such as turbidity or generation of precipitates was observed in this composition, and it was confirmed that the solution was a homogeneous solution. The composition (5) was also used for the evaluation as the liquid crystal alignment treatment agent (5).

Evaluation of printability of composition and liquid crystal alignment treatment agent (evaluation of pinhole), evaluation of printability of composition and liquid crystal alignment treatment agent (Evaluation of stepwise followability) &quot;, &quot; And &quot; preparation of liquid crystal cell and evaluation of pretilt angle (normal cell) &quot;.

&Lt; Example 6 &gt;

(0.93 g), BCS (5.83 g) and PB (8.74 g) were added to the polysiloxane solution 4 (15.5 g) obtained by the procedure of Synthetic Example 4 and stirred at 25 占 폚 for 3 hours to obtain a composition 6 ). No abnormality such as turbidity or generation of precipitates was observed in this composition, and it was confirmed that the solution was a homogeneous solution. The composition (6) was also used for the evaluation as the liquid crystal alignment treatment agent (6).

Evaluation of printability of composition and liquid crystal alignment treatment agent (evaluation of pinhole), evaluation of printability of composition and liquid crystal alignment treatment agent (evaluation of stepwise followability) &quot; (Production of Liquid Crystal Cell and Evaluation of Pretilt Angle (Normal Cell)), Production of Liquid Crystal Cell and Evaluation of Liquid Crystal Orientation (PSA Cell), Production of Liquid Crystal Cell and Evaluation of Liquid Crystal Orientation (SC-PVA Cell) Was carried out.

&Lt; Example 7 &gt;

S1 (8.52 g), PB (10.9 g) and? -BL (7.28 g) were added to the polysiloxane solution 4 (11.0 g) obtained by the procedure of Synthetic Example 4 and stirred at 25 占 폚 for 3 hours, (7). No abnormality such as turbidity or generation of precipitates was observed in this composition, and it was confirmed that the solution was a homogeneous solution. The composition (7) was used for evaluation as the liquid crystal alignment treatment agent (7).

Evaluation of inkjet application property of liquid crystal alignment treatment agent &quot;, &quot; production of liquid crystal cell and evaluation of pretilt angle (normal cell) &quot; were carried out using the obtained liquid crystal alignment treatment agent (7).

&Lt; Example 8 &gt;

EC (0.90 g), S1 (11.3 g) and NEP (2.82 g) were added to the polysiloxane solution 5 (15.0 g) obtained by the procedure of Synthetic Example 5 and stirred at 25 占 폚 for 3 hours to obtain a composition 8 ). No abnormality such as turbidity or generation of precipitates was observed in this composition, and it was confirmed that the solution was a homogeneous solution. The composition (8) was also used for the evaluation as the liquid crystal alignment treatment agent (8).

Evaluation of printability of composition and liquid crystal alignment treatment agent (evaluation of pinhole), evaluation of printability of composition and liquid crystal alignment treatment agent (evaluation of stepwise followability) &quot;, and &quot; And &quot; preparation of liquid crystal cell and evaluation of pretilt angle (normal cell) &quot;.

&Lt; Example 9 &gt;

K1 (0.09 g), EC (0.90 g), S1 (8.46 g), DME (2.82 g) and? -BL (2.82 g) were added to the polysiloxane solution (5) And the mixture was stirred at 25 캜 for 6 hours to obtain a composition (9). No abnormality such as turbidity or generation of precipitates was observed in this composition, and it was confirmed that the solution was a homogeneous solution. The composition (9) was also used for the evaluation as the liquid crystal alignment treatment agent (9).

Evaluation of printability of composition and liquid crystal alignment treatment agent (evaluation of pinhole), evaluation of printability of composition and liquid crystal alignment treatment agent (evaluation of stepwise followability) &quot; And &quot; preparation of liquid crystal cell and evaluation of pretilt angle (normal cell) &quot;.

&Lt; Example 10 &gt;

EC (8.52 g), S1 (12.7 g), DME (1.82 g) and? -BL (3.64 g) were added to the polysiloxane solution 5 (11.0 g) obtained by the procedure of Synthetic Example 5, Followed by stirring for 3 hours to obtain a composition (10). No abnormality such as turbidity or generation of precipitates was observed in this composition, and it was confirmed that the solution was a homogeneous solution. The composition (10) was used for evaluation as the liquid crystal alignment treatment agent (10).

Evaluation of inkjet application property of liquid crystal alignment treatment agent &quot;, &quot; production of liquid crystal cell and evaluation of pretilt angle (normal cell) &quot; were performed using the obtained liquid crystal alignment treatment agent 10.

&Lt; Example 11 &gt;

EC (0.96 g), S1 (12.0 g) and PB (3.01 g) were added to the polysiloxane solution 6 (16.0 g) obtained by the procedure of Synthetic Example 6 and stirred at 25 占 폚 for 3 hours to obtain a composition 11 ). No abnormality such as turbidity or generation of precipitates was observed in this composition, and it was confirmed that the solution was a homogeneous solution.

Evaluation of the printability of the composition and the liquid crystal alignment treatment agent (evaluation of pinhole) &quot; and the evaluation of the printability of the composition and liquid crystal alignment treatment agent (evaluation of the stepwise followability) were carried out using the obtained composition (11).

&Lt; Example 12 &gt;

(6.98 g), BCS (6.02 g) and PB (3.01 g) were added to the polysiloxane solution 7 (16.0 g) obtained by the method of Synthetic Example 7 and stirred at 25 占 폚 for 3 hours to obtain a composition 12 ). No abnormality such as turbidity or generation of precipitates was observed in this composition, and it was confirmed that the solution was a homogeneous solution.

Evaluation of printability of the composition and liquid crystal alignment treatment agent (evaluation of pinhole) &quot; and evaluation of printability of composition and liquid crystal alignment treatment agent (evaluation of stepwise followability) were carried out using the obtained composition (12).

&Lt; Example 13 &gt;

EC (0.90 g), S1 (11.3 g), DME (1.41 g) and NEP (1.41 g) were added to the polysiloxane solution 8 (15.0 g) obtained by the procedure of Synthetic Example 8, Followed by stirring to obtain a composition (13). No abnormality such as turbidity or generation of precipitates was observed in this composition, and it was confirmed that the solution was a homogeneous solution.

Evaluation of printability of composition and liquid crystal alignment treatment agent (evaluation of pinhole) &quot; and evaluation of printability of composition and liquid crystal alignment treatment agent (evaluation of stepwise followability) were performed using composition (13).

&Lt; Comparative Example 1 &

EC (9.98 g) and BCS (6.02 g) were added to the polysiloxane solution (1) (16.0 g) obtained by the procedure of Synthesis Example 1 and stirred at 25 占 폚 for 3 hours to obtain Composition (14). No abnormality such as turbidity or generation of precipitates was observed in this composition, and it was confirmed that the solution was a homogeneous solution. The composition (14) was also used for the evaluation as the liquid crystal alignment treatment agent (14).

Evaluation of printability of the composition and liquid crystal alignment treatment agent (evaluation of pinhole) &quot;, &quot; evaluation of printability of composition and liquid crystal alignment treatment agent (evaluation of stepwise followability) &quot; And &quot; preparation of liquid crystal cell and evaluation of pretilt angle (normal cell) &quot;.

&Lt; Comparative Example 2 &

EC (9.98 g) and BCS (6.02 g) were added to the polysiloxane solution (2) (16.0 g) obtained by the procedure of Synthetic Example 2 and stirred at 25 占 폚 for 3 hours to obtain Composition (15). No abnormality such as turbidity or generation of precipitates was observed in this composition, and it was confirmed that the solution was a homogeneous solution. The composition (15) was also used for evaluation as the liquid crystal alignment treatment agent (15).

Evaluation of printability of composition and liquid crystal alignment treatment agent (evaluation of pinhole), evaluation of printability of composition and liquid crystal alignment treatment agent (evaluation of stepwise followability) &quot;, &quot; And &quot; preparation of liquid crystal cell and evaluation of pretilt angle (normal cell) &quot;.

&Lt; Comparative Example 3 &

EC (12.2 g) and PB (2.82 g) were added to the polysiloxane solution 6 (15.0 g) obtained by the procedure of Synthesis Example 6 and stirred at 25 占 폚 for 3 hours to obtain Composition (16). No abnormality such as turbidity or generation of precipitates was observed in this composition, and it was confirmed that the solution was a homogeneous solution.

Evaluation of printability of composition and liquid crystal alignment treatment agent (evaluation of pinhole) &quot; and evaluation of printability of composition and liquid crystal alignment treatment agent (evaluation of stepwise followability) were performed using composition (16).

* 1: Represents the percentage of a specific solvent when the total solvent is 100.

* 2: represents the ratio of other solvents when the total solvent is 100.

* 3: Represents the proportion of the polymer and the polymer in the liquid crystal alignment treatment agent.

* 1: Represents the percentage of a specific solvent when the total solvent is 100.

* 2: represents the ratio of other solvents when the total solvent is 100.

* 3: Represents the proportion of the polymer and the polymer in the liquid crystal alignment treatment agent.

* 1: Represents the percentage of a specific solvent when the total solvent is 100.

* 2: represents the ratio of other solvents when the total solvent is 100.

* 3: Represents the proportion of the polymer and the polymer in the liquid crystal alignment treatment agent.

As can be seen from the above results, the polyimide film obtained from the composition of the example of the present invention exhibited a uniform film-like property free from pinholes as compared with the polyimide film obtained from the composition of the comparative example. Furthermore, a resin coating having a high step-following ability with respect to the unevenness of the stepped substrate was obtained.

Specifically, the comparison between the composition using the specific solvent (A) of the present invention and the composition not using it, that is, the comparison between Example 1 and Comparative Example 1, the comparison between Example 2 and Comparative Example 2, and the comparison This is a comparison of Example 11 and Comparative Example 3. In these Comparative Examples, the number of pinholes on the resin coating film was larger than that in the corresponding Examples, and the step-wise followability to the unevenness of the stepped substrate was also lowered. In addition, the compositions of these examples were also used as evaluators as liquid crystal alignment treatment agents, and the results of the examples using these compositions were also the results of liquid crystal alignment treatment agents.

In addition, the liquid crystal alignment treatment agent using the component (A) of the present invention is superior to the liquid crystal alignment treatment agent that does not use the component (A) because the change of the pretilt angle after the high temperature storage of the pretilt angle immediately after the production of the liquid crystal cell and after the ultraviolet irradiation It became smaller. That is, the stability of the pretilt angle with respect to high temperature and ultraviolet ray was high. Specifically, the comparison between Example 1 and Comparative Example 1 and the comparison between Example 2 and Comparative Example 2 are made.

In addition, when the structure represented by the formula [2a-1] is used as the specific side chain structure of the present invention, the change of the pretilt angle after the high temperature storage of the pretilt angle immediately after the liquid crystal cell fabrication and after the ultraviolet irradiation . Specifically, it is a comparison between Example 1 and Example 2. [

Industrial availability

The composition of the present invention can suppress the occurrence of pinholes when forming a resin film, and further can obtain a resin film having a step-following property with respect to the unevenness of the stepped substrate.

Further, by using the composition of the present invention as a liquid crystal alignment treatment agent, the occurrence of pinholes can be suppressed, and further, a liquid crystal alignment film having a step-following ability with respect to the unevenness of the stepped substrate can be obtained. Further, the liquid crystal alignment treatment agent of the present invention becomes a liquid crystal alignment film capable of exhibiting a stable pretilt angle even after exposure to high temperature and light irradiation for a long time.

Therefore, the liquid crystal display element having the liquid crystal alignment film obtained from the liquid crystal alignment treatment agent of the present invention is excellent in reliability, and can be preferably used for a large-screen liquid crystal television, a small and medium-sized car navigation system or a smart phone, , An STN device, and a TFT liquid crystal device, particularly VA mode, PSA mode and SC-PVA mode.

Claims (20)

Component (A): The following formula [1]:
[Chemical Formula 1]

(Wherein X ¹ and X ² each independently represent an alkyl group having 1 to 3 carbon atoms, and X ³ and X ⁴ each independently represent an alkyl group having 1 to 3 carbon atoms); And
Component (B): The following formulas [2a], [2b] and [2c]
(2)

Wherein A ¹ is a group represented by the following formulas [2a-1] and [2a-2]:
(3)

(Wherein, Y ¹ represents a single _{bond, - (CH 2) a -} (a is an integer of 1 ~ 15), -O-, -CH 2 O-, -CONH-, -NHCO-, -CON (CH _{3) -, -N (CH 3} ) it represents at least one coupler is selected from CO-, -COO- and -OCO-, Y ² is a single bond or _{- (CH 2) b - (} b is 1 to 15 represents a an integer), Y ³ represents a single _{bond, - (CH 2) c -} (c is an integer of 1 ~ 15), -O-, -CH 2 O-, -COO- and -OCO- selected from Y ⁴ represents at least one kind of cyclic group selected from a benzene ring, a cyclohexane ring and a heterocyclic ring, or a divalent organic group having a steroid skeleton and having from 17 to 51 carbon atoms, and the cyclic group ^May be substituted with an alkyl group having 1 to 3 carbon atoms, an alkoxyl group having 1 to 3 carbon atoms, a fluorine-containing alkyl group having 1 to 3 carbon atoms, a fluoro-containing alkoxyl group having 1 to 3 carbon atoms, or a fluorine atom, Benzene ring, cyclohexyl An alkyl group having 1 to 3 carbon atoms, an alkoxyl group having 1 to 3 carbon atoms, a fluorine-containing alkyl group having 1 to 3 carbon atoms, a fluorine-containing alkyl group having 1 to 3 carbon atoms, N is an integer of 0 to 4, Y ⁶ is an alkyl group having 1 to 22 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, a fluorine atom having 1 to 22 carbon atoms, a fluorine-containing alkoxyl group having 1 to 3 carbon atoms, Containing alkyl group, an alkoxyl group having 1 to 22 carbon atoms, and a fluorinated alkoxyl group having 1 to 22 carbon atoms) and
[Chemical Formula 4]

(Wherein Y ⁷ represents a single bond, -O-, -CH ₂ O-, -CONH-, -NHCO-, -CON (CH ₃ ) -, -N (CH ₃ ) CO-, OCO- and Y ⁸ represents an alkyl group having from 8 to 22 carbon atoms or a fluorine-containing alkyl group having from 6 to 18 carbon atoms), and A &lt; ² &gt; represents at least one structure selected from the group consisting of Each independently represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, A ³ each independently represents an alkyl group having 1 to 5 carbon atoms, m ¹ represents an integer of 1 or 2, and n ¹ represents 0 to 2 And p ¹ represents an integer of 0 to 3, provided that m ¹ + n ¹ + p ¹ is an integer of 4);
[Chemical Formula 5]

Wherein B ¹ each independently represents a group having 2 to 12 carbon atoms having at least one kind selected from a vinyl group, an epoxy group, an amino group, a mercapto group, an isocyanate group, a methacryl group, an acrylic group, an ureido group and a cinnamoyl group B ² each independently represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms; B ³ independently represents an alkyl group having 1 to 5 carbon atoms or an alkoxyalkyl group having 1 to 5 carbon atoms; and m ² Represents an integer of 1 or 2, n ² represents an integer of 0 to 2, and p ² represents an integer of 0 to 3, provided that m ² + n ² + p ² represents an integer of 4); And
[Chemical Formula 6]

(Wherein D ¹ each independently represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, D ² each independently represents an alkyl group having 1 to 5 carbon atoms, and n ³ represents an integer of 0 to 3)
And alkoxysilane represented by the following general formula (1): &quot; (1) &quot; The method according to claim 1,
Wherein the solvent of the component (A) is a compound represented by the following formula [1a]:
(7)

&Lt; / RTI &gt; 3. The method according to claim 1 or 2,
Wherein the alkoxysilane represented by the formula [2b] of the component (B) is at least one selected from the group consisting of allyltriethoxysilane, allyltrimethoxysilane, diethoxymethylvinylsilane, dimethoxymethylvinylsilane, triethoxvinylsilane, vinyltrimethoxy Silane, vinyltris (2-methoxyethoxy) silane, 3- (triethoxysilyl) propyl methacrylate, 3- (trimethoxysilyl) propyl acrylate and 3- (trimethoxysilyl) Lt; RTI ID = 0.0 &gt; alkoxysilane &lt; / RTI &gt; 3. The method according to claim 1 or 2,
Wherein the alkoxysilane represented by the formula [2b] of the component (B) is at least one member selected from the group consisting of 3-glycidyloxypropyl (dimethoxy) methylsilane, 3-glycidyloxypropyl (diethoxy) methylsilane, 3-glycidyloxy Propyl trimethoxysilane, and 2- (3,4-epoxycyclohexyl) ethyl trimethoxysilane. 5. The method according to any one of claims 1 to 4,
Wherein the polysiloxane of the component (B) is a polysiloxane obtained by polycondensation of an alkoxysilane represented by the formula [2a] and a formula [2b], or a polysiloxane obtained by polycondensation of an alkoxysilane represented by the formula [2a] and a formula [2c] Wherein the composition is a polysiloxane comprising any one polysiloxane. 6. The method according to any one of claims 1 to 5,
Wherein the polysiloxane of the component (B) is a polysiloxane obtained by polycondensation of an alkoxysilane represented by the formula [2a], the formula [2b] and the formula [2c]. 7. The method according to any one of claims 1 to 6,
In the composition, at least one compound selected from the group consisting of methyl ethyl ketone, cyclohexanone, cyclopentanone, 4-hydroxy-4-methyl-2-pentanone, 1-hexanol, cyclohexanol, , 1,4-butanediol, 2,3-butanediol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl At least one solvent selected from ether, ethylene glycol monopropyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, dipropylene glycol monomethyl ether, dipropylene glycol dimethyl ether and furfuryl alcohol &Lt; / RTI &gt; 8. The method according to any one of claims 1 to 7,
Wherein the composition contains at least one solvent selected from N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone,? -Butyrolactone and 1,3-dimethyl- Composition. 9. The method according to any one of claims 1 to 8,
A crosslinkable compound having an epoxy group, an isocyanate group, an oxetane group or a cyclocarbonate group, a crosslinkable compound having at least one substituent selected from the group consisting of a hydroxyl group, a hydroxyalkyl group and a lower alkoxyalkyl group, At least one crosslinkable compound selected from crosslinkable compounds having unsaturated bonds. 10. The method according to any one of claims 1 to 9,
Wherein the component (A) is 20 to 80 mass% of the total solvent contained in the composition. 11. The method according to any one of claims 1 to 10,
Wherein the component (B) is 0.1% by mass to 30% by mass in the composition. A resin film obtained from the composition according to any one of claims 1 to 11. A liquid crystal alignment treatment agent obtained from the composition according to any one of claims 1 to 11. A liquid crystal alignment film obtained by using the liquid crystal alignment treatment agent according to claim 13. A liquid crystal alignment film obtained by the ink jet method using the liquid crystal alignment treatment agent according to claim 13. A liquid crystal display element having the liquid crystal alignment film according to claim 14 or 15. 16. The method according to claim 14 or 15,
A liquid crystal composition comprising a liquid crystal layer between a pair of substrates provided with electrodes and comprising a polymerizable compound capable of polymerizing by at least one of active energy rays and heat is arranged between the pair of substrates, Wherein the polymerizable compound is used in a liquid crystal display device manufactured through a step of polymerizing the polymerizable compound while applying a voltage to the liquid crystal alignment film. A liquid crystal display element having the liquid crystal alignment film according to claim 17. 16. The method according to claim 14 or 15,
A liquid crystal alignment film comprising a liquid crystal layer between a pair of substrates provided with electrodes and comprising a polymerizable group capable of polymerizing by at least one of active energy rays and heat is disposed between the pair of substrates, Wherein the liquid crystal alignment film is used for a liquid crystal display device manufactured through a process of polymerizing the polymerizable group while applying a voltage. A liquid crystal display element having the liquid crystal alignment film according to claim 19.

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