KR102261699B1 - Method for producing substrate having liquid crystal orientation membrane for use in in-plane-switching liquid crystal display element - Google Patents

Abstract

The present invention provides a transverse electric field driving type liquid crystal display device which is highly efficient, has orientation controllability, and has excellent exposure characteristics. The present invention is (A) a photosensitive side chain polymer which expresses liquid crystallinity in a predetermined temperature range, (B) a hydroxyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an oxirane group, an epoxy group, an isocyanate group, In a polymer composition comprising a crosslinkable compound having two or more substituents in one molecule of at least one substituent selected from an oxetane group, a cyclocarbonate group, a trialkoxysilyl group, and a polymerizable unsaturated bond group, and (C) an organic solvent By this, the said subject is solved. In particular, [I] a step of coating the composition on a substrate having a conductive film for lateral electric field drive to form a coating film; [II] a step of irradiating the coating film obtained in [I] with polarized ultraviolet rays; and [III] ] Process of heating the coating film obtained by [II]; By having, the said subject is solved by the manufacturing method of the board|substrate which has a liquid crystal aligning film which obtains the liquid crystal aligning film for lateral electric field drive type liquid crystal display elements to which orientation control ability was provided.

Description

The manufacturing method of the board|substrate which has a liquid crystal aligning film for transverse electric field drive type liquid crystal display elements TECHNICAL FIELD

This invention relates to the manufacturing method of the board|substrate which has a liquid crystal aligning film for transverse electric field drive type liquid crystal display elements. More specifically, it relates to a novel method for manufacturing a liquid crystal display device having excellent exposure characteristics.

BACKGROUND ART Liquid crystal display elements are known as light-weight, thin, and low-power display devices, and in recent years they have been used for large-sized televisions, and have achieved remarkable development. A liquid crystal display element clamps a liquid crystal layer with a pair of transparent board|substrates provided with an electrode, and is comprised, for example. And in a liquid crystal display element, the organic film which consists of an organic material is used as a liquid crystal aligning film so that a liquid crystal may become a desired orientation state between board|substrates.

That is, the liquid crystal aligning film is a structural member of a liquid crystal display element, it is formed in the surface in contact with the liquid crystal of the board|substrate which clamps a liquid crystal, and plays the role of orientating a liquid crystal in a fixed direction between the board|substrates. And in addition to the role of orientating a liquid crystal in fixed directions, such as a direction parallel to a board|substrate, the role of controlling the pretilt angle of a liquid crystal may be calculated|required by a liquid crystal aligning film, for example. The ability to control the orientation of a liquid crystal in such a liquid crystal aligning film (it is hereafter called orientation control ability.) is provided by orientation-processing with respect to the organic film which comprises a liquid crystal aligning film.

As an orientation processing method of the liquid crystal aligning film for providing orientation control ability, the rubbing method is conventionally known. The rubbing method refers to rubbing (rubbing) the surface of an organic film such as polyvinyl alcohol, polyamide, or polyimide on a substrate with a cloth such as cotton, nylon, or polyester in a certain direction (rubbing direction), and rubbing direction (rubbing direction) A method of aligning liquid crystals with Since this rubbing method can implement|achieve the orientation state of a relatively stable liquid crystal easily, it has been used in the manufacturing process of the conventional liquid crystal display element. And as an organic film used for a liquid crystal aligning film, the polyimide-type organic film excellent in reliability, such as heat resistance, and electrical characteristic has been mainly selected.

However, in the rubbing method of rubbing the surface of the liquid crystal aligning film which consists of polyimide etc., generation|occurrence|production of dust and static electricity may become a problem. In addition, due to the recent increase in precision of liquid crystal display elements and the irregularities caused by the electrodes on the corresponding substrates and the switching active elements for driving liquid crystals, the surface of the liquid crystal aligning film cannot be uniformly rubbed with a cloth, and uniform liquid crystal alignment can be realized. There were cases where there was no

Then, as another orientation processing method of the liquid crystal aligning film which does not rub, the photo-alignment method is examined actively.

Although there are various methods in the photo-alignment method, anisotropy is formed in the organic film which comprises a liquid crystal aligning film by linearly polarized light or collimated light, and a liquid crystal is orientated according to the anisotropy.

As a main photo-alignment method, the decomposition-type photo-alignment method is known. For example, a polyimide film is irradiated with polarized ultraviolet light, and anisotropic decomposition is generated using the polarization direction dependence of the ultraviolet absorption of the molecular structure. And it is made to orientate a liquid crystal by the polyimide which remained without decomposition|disassembly (for example, refer patent document 1).

Moreover, the photo-alignment method of a photocrosslinking type|mold and a photoisomerization type is also known. For example, using polyvinylcinnamate, polarized ultraviolet rays are irradiated, and a dimerization reaction (crosslinking reaction) is generated in the double bond portion of two side chains parallel to polarization. Then, the liquid crystal is aligned in a direction orthogonal to the polarization direction (for example, refer to Non-Patent Document 1). In addition, when a side chain polymer having azobenzene in the side chain is used, polarized ultraviolet light is irradiated to cause an isomerization reaction in the azobenzene moiety of the side chain parallel to polarization, and the liquid crystal is oriented in a direction orthogonal to the polarization direction (eg For example, refer to Non-Patent Document 2.).

As in the above example, in the orientation processing method of the liquid crystal aligning film by a photo-alignment method, rubbing is made unnecessary, and there is no possibility of generation|occurrence|production of dust and static electricity. And it can orientation-process also to the board|substrate of the liquid crystal display element with an unevenness|corrugation on the surface, and it becomes the method of the orientation treatment of the liquid crystal aligning film suitable for an industrial production process.

Japanese Patent Publication No. 3893659

M. Shadt et al., Jpn. J. Appl. Phys. 31, 2155 (1992). K. Ichimura et al., Chem. Rev. 100, 1847 (2000).

As mentioned above, the photo-alignment method makes the rubbing process itself unnecessary compared with the rubbing method which has been conventionally used industrially as an orientation processing method of a liquid crystal display element, Therefore, it is equipped with a big advantage. And compared with the rubbing method in which orientation controllability becomes substantially constant by rubbing, by the photo-alignment method, the irradiation amount of the polarized light can be changed and orientation controllability can be controlled. However, in the photo-alignment method, when it is intended to realize the same degree of alignment control ability as in the case of the rubbing method, a large amount of polarized light irradiation is required, or stable alignment of the liquid crystal cannot be realized in some cases.

For example, in the decomposition-type photo-alignment method described in Patent Document 1 described above, it is necessary to irradiate the polyimide film with ultraviolet light from a high-pressure mercury lamp having an output of 500 W for 60 minutes. will be needed Moreover, also in the case of the photo-alignment method of a dimerization type|mold or a photoisomerization type|mold, the ultraviolet irradiation of the large quantity of about several J (joule) - several tens of J may be required. Moreover, in the case of the photo-alignment method of a photocrosslinking type or a photoisomerization type, since thermal stability and light stability of liquid crystal orientation were inferior, when it was set as a liquid crystal display element, there existed a problem that orientation defect and display exposure generate|occur|produced. In particular, in a liquid crystal display element of a transverse electric field drive type, since liquid crystal molecules are switched in-plane, the orientation shift of the liquid crystal after liquid crystal drive is easy to occur, and display exposure resulting from AC drive becomes a big problem.

Therefore, in the photo-alignment method, high efficiency improvement of an orientation process and realization of the stable liquid-crystal orientation are calculated|required, and the liquid crystal aligning film and liquid crystal aligning agent which can provide high orientation control ability with respect to a liquid crystal aligning film with high efficiency are calculated|required.

An object of the present invention is to provide a substrate having a liquid crystal aligning film for a transverse electric field driving type liquid crystal display element, which is highly efficient in orientation controllability and excellent in exposure characteristics, and a transverse electric field driving type liquid crystal display element having the substrate.

In addition, an object of the present invention is to improve the film density of the liquid crystal aligning film in addition to the above object, without moving impurities present in the liquid crystal aligning film to the liquid crystal side, and having an improved voltage retention rate for a transverse electric field driving type liquid crystal element and for the element It exists to provide a liquid crystal aligning film.

In addition, an object of the present invention is to provide a transverse electric field driving type liquid crystal element having improved adhesion and a liquid crystal aligning film for the element by increasing the interaction of the liquid crystal aligning film and the sealing agent in addition to or in addition to the above object have.

MEANS TO SOLVE THE PROBLEM The present inventors discovered the following invention, as a result of earnestly examining in order to achieve the said subject.

<1> (A) the photosensitive side chain type polymer|macromolecule which expresses liquid crystallinity in a predetermined|prescribed temperature range;

(B) at least one selected from a hydroxyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an oxirane group, an epoxy group, an isocyanate group, an oxetane group, a cyclocarbonate group, a trialkoxysilyl group, and a polymerizable unsaturated bond group A crosslinkable compound having two or more substituents in one molecule, and

(C) organic solvent

A polymer composition containing

In <2> said <1>, it is good for (A) component to have a photosensitive side chain which raise|generates photocrosslinking, photoisomerization, or optical fleece transition.

In <3> said <1> or <2>, it is good for (A) component to have any 1 type of photosensitive side chain chosen from the group which consists of following formula (1)-(6).

[Formula 1]

In the formula, A, B, D are each independently a single bond, -O-, -CH ₂ -, -COO-, -OCO-, -CONH-, -NH-CO-, -CH=CH-CO-O - or -O-CO-CH=CH- is represented;

S is a C1-C12 alkylene group, and the hydrogen atom couple|bonded with them may be substituted by the halogen group;

T is a single bond or an alkylene group having 1 to 12 carbon atoms, and the hydrogen atom bonded thereto may be substituted with a halogen group;

Y ₁ represents a ring selected from a monovalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring and an alicyclic hydrocarbon having 5 to 8 carbon atoms, or the same or different 2 to 6 rings selected from their substituents is a group formed by bonding via a bonding group B, and the hydrogen atoms bonded thereto are each independently -COOR ₀ (wherein R ₀ represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms), -NO ₂ , - CN, -CH=C(CN) ₂ , -CH=CH-CN, a halogen group, a C1-C5 alkyl group, or a C1-C5 alkyloxy group may be substituted;

Y ₂ is a group selected from the group consisting of a divalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring, an alicyclic hydrocarbon having 5 to 8 carbon atoms, and combinations thereof, and a hydrogen atom bonded thereto is each independently -NO ₂ , -CN, -CH=C(CN) ₂ , -CH=CH-CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or an alkyloxy group having 1 to 5 carbon atoms;

R represents a hydroxy group, an alkoxy group having 1 to 6 carbon atoms, or has the same definition as _{Y 1 ;}

X is a single bond, -COO-, -OCO-, -N=N-, -CH=CH-, -C≡C-, -CH=CH-CO-O-, or -O-CO-CH=CH - and when the number of X becomes 2, X may be the same or different;

Cou represents a coumarin-6-yl group or a coumarin-7-yl group, and hydrogen atoms bonded thereto are each independently -NO ₂ , -CN, -CH=C(CN) ₂ , -CH=CH-CN, halogen group, a C1-C5 alkyl group, or a C1-C5 alkyloxy group may be substituted;

one of q1 and q2 is 1 and the other is 0;

q3 is 0 or 1;

P and Q are each independently a group selected from the group consisting of a divalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring, an alicyclic hydrocarbon having 5 to 8 carbon atoms, and combinations thereof; When is -CH=CH-CO-O-, -O-CO-CH=CH-, P or Q on the side to which -CH=CH- is bonded is an aromatic ring, and when the number of P is 2 or more, P may be the same or different, and when the number of Q becomes 2 or more, Q may be same or different;

l1 is 0 or 1;

l2 is an integer of 0 to 2;

When both l1 and l2 are 0, when T is a single bond, A also represents a single bond;

When l1 is 1, when T is a single bond, B also represents a single bond;

H and I are each independently a group selected from a divalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring, and combinations thereof.

In <4> said <1> or <2>, it is good for (A) component to have any 1 type of photosensitive side chain chosen from the group which consists of following formula (7) - (10).

wherein A, B, D, Y ₁ , X, Y ₂ , and R have the same definitions as above;

l represents the integer of 1-12;

m represents the integer of 0-2, m1, m2 represents the integer of 1-3;

n represents an integer of 0 to 12 (provided that when n = 0, B is a single bond).

[Formula 2]

In <5> said <1> or <2>, it is good for (A) component to have any 1 type of photosensitive side chain chosen from the group which consists of following formula (11)-(13).

In the formula, A, X, l, m, m1 and R have the same definitions as above.

[Formula 3]

In <6> said <1> or <2>, it is good for (A) component to have a photosensitive side chain represented by following formula (14) or (15).

In the formula, A, Y ₁ , l, m1 and m2 have the same definitions as above.

[Formula 4]

In <7> said <1> or <2>, it is good for (A) component to have a photosensitive side chain represented by following formula (16) or (17).

In the formula, A, X, l and m have the same definitions as above.

[Formula 5]

In <8> said <1> or <2>, it is good for (A) component to have a photosensitive side chain represented by following formula (18) or (19).

In the formula, A, B, Y ₁ , q1, q2, m1, and m2 have the same definitions as above.

R ₁ represents a hydrogen atom, -NO ₂ , -CN, -CH=C(CN) ₂ , -CH=CH-CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or an alkyloxy group having 1 to 5 carbon atoms.

[Formula 6]

In <9> said <1> or <2>, it is good for (A) component to have a photosensitive side chain represented by following formula (20).

In the formula, A, Y ₁ , X, l and m have the same definitions as above.

[Formula 7]

<10> In any one of said <1>-<9>, it is good for (A) component to have any 1 type of liquid crystalline side chain chosen from the group which consists of following formula (21)-(31) .

wherein A, B, q1 and q2 have the same definitions as above;

Y ₃ is a group selected from the group consisting of a monovalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a nitrogen-containing heterocyclic ring, an alicyclic hydrocarbon having 5 to 8 carbon atoms, and combinations thereof, The hydrogen atoms may each independently be _{substituted with -NO 2} , -CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or an alkyloxy group having 1 to 5 carbon atoms;

R ₃ is a hydrogen atom, -NO ₂ , -CN, -CH=C(CN) ₂ , -CH=CH-CN, a halogen group, a monovalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a nitrogen-containing hetero a ring, an alicyclic hydrocarbon having 5 to 8 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms;

l represents an integer of 1 to 12, m represents an integer of 0 to 2, with the proviso that in Formulas (23) to (24), the sum of all m is 2 or more, and Formulas (25) to (26) In , the sum of all m is 1 or more, and m1, m2, and m3 each independently represent an integer of 1 to 3;

R ₂ is a hydrogen atom, —NO ₂ , —CN, a halogen group, a monovalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a nitrogen-containing heterocyclic ring, and an alicyclic hydrocarbon having 5 to 8 carbon atoms, and an alkyl group; or an alkyloxy group;

Z ₁ , Z ₂ represents a single bond, -CO-, -CH ₂ O-, -CH=N-, -CF ₂ -.

[Formula 8]

<11> [I] The process of apply|coating the composition in any one of said <1>-<10> on the board|substrate which has an electrically conductive film for lateral electric field drive, and forming a coating film;

[II] The process of irradiating the polarized ultraviolet-ray to the coating film obtained in [I]; And

[III] Process of heating the coating film obtained in [II];

The manufacturing method of the board|substrate which has the said liquid crystal aligning film which obtains the liquid crystal aligning film for transverse electric field drive type liquid crystal display elements to which orientation control ability was provided by having.

<12> The board|substrate which has the liquid crystal aligning film for lateral electric field drive type liquid crystal display elements manufactured by the method of said <11>.

<13> Transverse electric field drive type liquid crystal display element which has the board|substrate of said <12>.

<14> Step of preparing the substrate (first substrate) of <12> above;

[I'] on the second substrate

(A) a photosensitive side chain polymer which expresses liquid crystallinity in a predetermined temperature range;

(B) at least one selected from a hydroxyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an oxirane group, an epoxy group, an isocyanate group, an oxetane group, a cyclocarbonate group, a trialkoxysilyl group, and a polymerizable unsaturated bond group A crosslinkable compound having two or more substituents in one molecule, and

(C) organic solvent

A step of forming a coating film by applying a polymer composition containing;

[II'] The process of irradiating the polarized ultraviolet-ray to the coating film obtained by [I']; And

[III'] The process of heating the coating film obtained by [II'];

The process of obtaining the 2nd board|substrate which has the said liquid crystal aligning film which obtains the liquid crystal aligning film to which orientation control ability was provided by having; And

[IV] The process of opposingly arrange|positioning a said 1st and 2nd board|substrate and obtaining a liquid crystal display element so that the liquid crystal aligning film of a said 1st and 2nd board|substrate may oppose through a liquid crystal;

The manufacturing method of the liquid crystal display element which obtains a transverse electric field drive type liquid crystal display element by having.

<15> A transverse electric field driving type liquid crystal display device manufactured by the method of <14>.

Moreover, as another aspect, the following invention was discovered.

<P1> [I] (A) The photosensitive side chain type polymer|macromolecule which expresses liquid crystallinity in a predetermined|prescribed temperature range;

(B) at least one selected from a hydroxyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an oxirane group, an epoxy group, an isocyanate group, an oxetane group, a cyclocarbonate group, a trialkoxysilyl group, and a polymerizable unsaturated bond group A crosslinkable compound having two or more substituents in one molecule, and

(C) organic solvent

A step of forming a coating film by applying a polymer composition comprising: on a substrate having a conductive film for lateral electric field drive;

[II] The process of irradiating the polarized ultraviolet-ray to the coating film obtained in [I]; And

[III] Process of heating the coating film obtained in [II];

The manufacturing method of the board|substrate which has the said liquid crystal aligning film which obtains the liquid crystal aligning film for transverse electric field drive type liquid crystal display elements to which orientation control ability was provided by having.

<P2> In said <P1>, it is good for (A) component to have a photosensitive side chain which raise|generates photocrosslinking, photoisomerization, or optical fleece transition.

In <P3> said <P1> or <P2>, it is good for (A) component to have any 1 type of photosensitive side chain chosen from the group which consists of following formula (1)-(6).

[Formula 9]

In the formula, A, B, D are each independently a single bond, -O-, -CH ₂ -, -COO-, -OCO-, -CONH-, -NH-CO-, -CH=CH-CO- represents O- or -O-CO-CH=CH-;

S is a C1-C12 alkylene group, and the hydrogen atom couple|bonded with them may be substituted by the halogen group;

T is a single bond or an alkylene group having 1 to 12 carbon atoms, and the hydrogen atom bonded thereto may be substituted with a halogen group;

Y ₁ represents a ring selected from a monovalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring and an alicyclic hydrocarbon having 5 to 8 carbon atoms, or the same or different 2 to 6 rings selected from their substituents is a group formed by bonding via a bonding group B, and the hydrogen atoms bonded thereto are each independently -COOR ₀ (wherein R ₀ represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms), -NO ₂ , - CN, -CH=C(CN) ₂ , -CH=CH-CN, a halogen group, a C1-C5 alkyl group, or a C1-C5 alkyloxy group may be substituted;

Y ₂ is a group selected from the group consisting of a divalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring, an alicyclic hydrocarbon having 5 to 8 carbon atoms, and combinations thereof, and a hydrogen atom bonded thereto is each independently -NO ₂ , -CN, -CH=C(CN) ₂ , -CH=CH-CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or an alkyloxy group having 1 to 5 carbon atoms;

R represents a hydroxy group, an alkoxy group having 1 to 6 carbon atoms, or has the same definition as _{Y 1 ;}

X is a single bond, -COO-, -OCO-, -N=N-, -CH=CH-, -C≡C-, -CH=CH-CO-O-, or -O-CO-CH=CH - represents ;

Cou represents a coumarin-6-yl group or a coumarin-7-yl group, and hydrogen atoms bonded thereto are each independently -NO ₂ , -CN, -CH=C(CN) ₂ , -CH=CH-CN, halogen group, a C1-C5 alkyl group, or a C1-C5 alkyloxy group may be substituted;

As for q1 and q2, one is 1 and the other is 0;

q3 is 0 or 1;

P and Q are each independently a single bond, a divalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring, an alicyclic hydrocarbon having 5 to 8 carbon atoms, and a group selected from the group consisting of combinations thereof to be. However, when X is -CH=CH-CO-O-, -O-CO-CH=CH-, P or Q on the side to which -CH=CH- is bonded is an aromatic ring;

H and I are each independently a group selected from a divalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring, and combinations thereof.

In <P4> said <P1> or <P2>, it is good for (A) component to have any 1 type of photosensitive side chain chosen from the group which consists of following formula (7)-(10).

In the formula, A, B, D, Y ₁ , X, Y ₂ , and R have the same definitions as above;

l represents the integer of 1-12;

m represents the integer of 0-2, m1, m2 represents the integer of 1-3;

n represents an integer of 0 to 12 (provided that when n = 0, B is a single bond).

[Formula 10]

In <P5> said <P1> or <P2>, it is good for (A) component to have any 1 type of photosensitive side chain chosen from the group which consists of following formula (11)-(13).

In the formula, A, X, l, m and R have the same definitions as above.

[Formula 11]

<P6> Said <P1> or <P2> WHEREIN: It is good for (A) component to have a photosensitive side chain represented by following formula (14) or (15).

In the formula, A, Y ₁ , X, l, m1 and m2 have the same definitions as above.

[Formula 12]

<P7> Said <P1> or <P2> WHEREIN: It is good for (A) component to have a photosensitive side chain represented by following formula (16) or (17).

In the formula, A, X, l and m have the same definitions as above.

[Formula 13]

In <P8> said <P1> or <P2>, it is good for (A) component to have a photosensitive side chain represented by following formula (18) or (19).

In the formula, A, B, Y ₁ , q1, q2, m1, and m2 have the same definitions as above.

R ₁ represents a hydrogen atom, -NO ₂ , -CN, -CH=C(CN) ₂ , -CH=CH-CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or an alkyloxy group having 1 to 5 carbon atoms. .

[Formula 14]

<P9> In any one of said <P1> or <P2>, it is good for (A) component to have a photosensitive side chain represented by following formula (20).

In the formula, A, Y ₁ , X, l and m have the same definitions as above.

[Formula 15]

<P10> In any one of said <P1> - <P9>, (A) component has any 1 type of liquid crystalline side chain chosen from the group which consists of following formula (21) - (31) good.

wherein A, B, q1 and q2 have the same definitions as above;

Y ₃ is a group selected from the group consisting of a monovalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a nitrogen-containing heterocyclic ring, an alicyclic hydrocarbon having 5 to 8 carbon atoms, and combinations thereof, The hydrogen atoms may each independently be _{substituted with -NO 2} , -CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or an alkyloxy group having 1 to 5 carbon atoms;

R ₃ is a hydrogen atom, -NO ₂ , -CN, -CH=C(CN) ₂ , -CH=CH-CN, a halogen group, a monovalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a nitrogen-containing hetero a ring, an alicyclic hydrocarbon having 5 to 8 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms;

l represents an integer of 1 to 12, m represents an integer of 0 to 2, with the proviso that in formulas (25) to (26), the sum of all m is 2 or more, and formulas (27) to (28) In , the sum of all m is 1 or more, and m1, m2, and m3 each independently represent an integer of 1 to 3;

R ₂ is a hydrogen atom, —NO ₂ , —CN, a halogen group, a monovalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a nitrogen-containing heterocyclic ring, and an alicyclic hydrocarbon having 5 to 8 carbon atoms, and an alkyl group; or an alkyloxy group;

Z ₁ , Z ₂ represents a single bond, -CO-, -CH ₂ O-, -CH=N-, -CF ₂ -.

[Formula 16]

<P11> The board|substrate which has the liquid crystal aligning film for transverse electric field drive type liquid crystal display elements manufactured by any one of said <P1> - <P10>.

<P12> Transverse electric field drive type liquid crystal display element which has the board|substrate of said <P11>.

<P13> Step of preparing the substrate (first substrate) of the above <P11>;

[I'] on the second substrate

(A) a photosensitive side chain polymer which expresses liquid crystallinity in a predetermined temperature range;

(B) at least one selected from a hydroxyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an oxirane group, an epoxy group, an isocyanate group, an oxetane group, a cyclocarbonate group, a trialkoxysilyl group, and a polymerizable unsaturated bond group A crosslinkable compound having two or more substituents in one molecule, and

(C) organic solvent

A step of forming a coating film by applying a polymer composition containing;

[II'] The process of irradiating the ultraviolet-ray which polarized to the coating film obtained by [I'];

and

[III'] The process of heating the coating film obtained by [II'];

The process of obtaining the 2nd board|substrate which has this liquid crystal aligning film which obtains the liquid crystal aligning film to which orientation control ability was provided by having; And

[IV] Process of opposingly arrange|positioning a 1st and 2nd board|substrate so that the liquid crystal aligning film of a 1st and 2nd board|substrate may oppose through a liquid crystal, and obtaining a liquid crystal display element;

The manufacturing method of the liquid crystal display element which obtains a transverse electric field drive type liquid crystal display element by having.

<P14> The transverse electric field driving type liquid crystal display device manufactured according to <P13>.

<P15> (A) The photosensitive side chain type polymer|macromolecule which expresses liquid crystallinity in a predetermined|prescribed temperature range;

(B) at least one selected from a hydroxyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an oxirane group, an epoxy group, an isocyanate group, an oxetane group, a cyclocarbonate group, a trialkoxysilyl group, and a polymerizable unsaturated bond group A crosslinkable compound having two or more substituents in one molecule, and

(C) organic solvent

A composition for producing a liquid crystal aligning film for a transverse electric field driving type liquid crystal display device, containing.

ADVANTAGE OF THE INVENTION By this invention, orientation control ability is provided with high efficiency, and the board|substrate which has the liquid crystal aligning film for transverse electric field drive type liquid crystal display elements excellent in exposure characteristics, and the transverse electric field drive type liquid crystal display element which has this board|substrate can be provided.

Since the lateral electric field drive type liquid crystal display element manufactured by the method of this invention is highly efficient and orientation control ability is provided, even if it drives continuously for a long time, a display characteristic is not impaired.

In addition, according to the present invention, in addition to the above effects, the film density of the liquid crystal aligning film is improved so that impurities present in the liquid crystal aligning film are not moved to the liquid crystal side, and a transverse electric field driving type liquid crystal element having an improved voltage retention and for the element A liquid crystal aligning film may be provided.

In addition, according to the present invention, in addition to or in addition to the above effects, by increasing the interaction between the liquid crystal aligning film and the sealing agent, it is possible to provide a transverse electric field driving type liquid crystal element having improved adhesion and a liquid crystal aligning film for the element. have.

BRIEF DESCRIPTION OF THE DRAWINGS It is a figure of one example demonstrating typically the anisotropy introduction|transduction process in the manufacturing method of the liquid crystal aligning film used for this invention, A crosslinkable organic group is used for a photosensitive side chain, and introduce|transduced anisotropy is small. It is a drawing of the case.
It is a figure of one example explaining typically the anisotropy introduction|transduction process in the manufacturing method of the liquid crystal aligning film used for this invention, and the anisotropy introduce|transduced using a crosslinkable organic group for a photosensitive side chain is large. It is a drawing of the case.
3 : is a figure of one example explaining typically the anisotropic introduction|transduction process in the manufacturing method of the liquid crystal aligning film used for this invention, The organic group which raise|generates a fleece transition or isomerization in a photosensitive side chain is used, and introduce|transduced It is a diagram in the case of small anisotropy.
4 : is a figure of one example explaining typically the anisotropic introduction|transduction process in the manufacturing method of the liquid crystal aligning film used for this invention, The organic group which raise|generates a fleece transition or isomerization in a photosensitive side chain is used, and introduce|transduced It is a diagram in the case of large anisotropy.

MEANS TO SOLVE THE PROBLEM As a result of earnestly researching, this inventor came to complete this invention by obtaining the following knowledge.

The polymer composition used in the manufacturing method of this invention has a photosensitive side chain type polymer (hereinafter also simply referred to as side chain type polymer) which can express liquid crystallinity, and the coating film obtained using the said polymer composition is liquid crystal It is a film|membrane which has photosensitive side chain type polymer|macromolecule which can express. It orientation-processes by polarized light irradiation, without giving a rubbing process to this coating film. And it becomes a coating film (henceforth a liquid crystal aligning film) to which orientation control ability was provided through the process of heating the side chain type polymer film after polarized light irradiation. At this time, the slight anisotropy expressed by polarized light irradiation becomes a driving force, and liquid crystalline side chain type polymer|macromolecule itself is efficiently reorientated by self-organization. As a result, as a liquid crystal aligning film, highly efficient orientation processing is implement|achieved, and the liquid crystal aligning film to which high orientation control ability was provided can be obtained.

EMBODIMENT OF THE INVENTION Hereinafter, embodiment of this invention is described in detail.

<Method for manufacturing a substrate having a liquid crystal alignment film> and <Method for manufacturing a liquid crystal display element>

The manufacturing method of the board|substrate which has a liquid crystal aligning film of this invention,

[I] (A) The photosensitive side chain type polymer|macromolecule which expresses liquid crystallinity in a predetermined|prescribed temperature range;

(B) at least one selected from a hydroxyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an oxirane group, an epoxy group, an isocyanate group, an oxetane group, a cyclocarbonate group, a trialkoxysilyl group, and a polymerizable unsaturated bond group A crosslinkable compound having two or more substituents in one molecule, and

(C) organic solvent

A step of forming a coating film by applying a polymer composition comprising: on a substrate having a conductive film for lateral electric field drive;

[II] The process of irradiating the polarized ultraviolet-ray to the coating film obtained in [I]; And

[III] Process of heating the coating film obtained in [II];

has

According to the said process, the liquid crystal aligning film for transverse electric field drive type liquid crystal display elements to which orientation control ability was provided can be obtained, and the board|substrate which has this liquid crystal aligning film can be obtained.

Moreover, a transverse electric field drive type liquid crystal display element can be obtained by preparing a 2nd board|substrate other than the board|substrate (1st board|substrate) obtained above.

For the second substrate, the above steps [I] to [III] (the conductive film for lateral electric field drive) is used in the second substrate, except that a substrate not having a lateral electric field drive film is used instead of the substrate having the lateral electric field drive conductive film. In order to use the board|substrate which does not have, for convenience, in this application, it may abbreviate as process [I'] - [III']) By using), the 2nd board|substrate which has a liquid crystal aligning film to which orientation control ability was provided is obtained can

A method for manufacturing a transverse electric field driving type liquid crystal display device,

[IV] Process of opposingly arrange|positioning the 1st and 2nd board|substrate obtained above so that the liquid crystal aligning film of a 1st and 2nd board|substrate may oppose through a liquid crystal, and obtaining a liquid crystal display element;

has Thereby, a transverse electric field drive type liquid crystal display element can be obtained.

Hereinafter, each process of [I]-[III] and [IV] which the manufacturing method of this invention has is demonstrated.

<Process [I]>

In process [I], the photosensitive side chain type polymer|macromolecule which expresses liquid crystallinity in a predetermined|prescribed temperature range on the board|substrate which has the electrically conductive film for transverse electric field drive, a hydroxyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an oxy A crosslinkable compound having two or more substituents per molecule of at least one selected from a lan group, an epoxy group, an isocyanate group, an oxetane group, a cyclocarbonate group, a trialkoxysilyl group, and a polymerizable unsaturated bond group, and an organic solvent; The polymer composition containing it is apply|coated, and a coating film is formed.

<substrate>

Although limitation in particular is not carried out about a board|substrate, When the liquid crystal display element manufactured is a transmissive type, it is preferable that a board|substrate with high transparency is used. In that case, limitation in particular is not carried out, Plastic substrates, such as a glass substrate or an acrylic substrate and a polycarbonate board|substrate, etc. can be used.

Moreover, in consideration of application to a reflective liquid crystal display element, opaque substrates, such as a silicon wafer, can also be used.

<Conductive film for lateral electric field drive>

The substrate has a conductive film for driving a lateral electric field.

As this conductive film, when a liquid crystal display element is a transmissive type, although ITO (Indium Tin Oxide: Indium tin oxide), IZO (Indium Zinc Oxide: Indium zinc oxide), etc. are mentioned, It is not limited to these.

Moreover, in the case of a reflection type liquid crystal display element, although the material etc. which reflect light, such as aluminum, are mentioned as a conductive film, it is not limited to these.

A conventionally well-known method can be used for the method of forming a conductive film on a board|substrate.

<Polymer composition>

A polymer composition is apply|coated on the board|substrate which has the electrically conductive film for lateral electric field drive, especially on the electrically conductive film.

The polymer composition used for the manufacturing method of this invention is (A) photosensitive side chain type polymer|macromolecule which expresses liquid crystallinity in a predetermined|prescribed temperature range; (B) a hydroxyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group , A crosslinkable compound having at least one substituent selected from an oxirane group, an epoxy group, an isocyanate group, an oxetane group, a cyclocarbonate group, a trialkoxysilyl group, and a polymerizable unsaturated bond group in one molecule of two or more; and ( C) an organic solvent;

contains

<<(A) side chain type polymer>>

(A) A component is photosensitive side chain type polymer|macromolecule which expresses liquid crystallinity in a predetermined|prescribed temperature range.

(A) It is good that side chain type polymer|macromolecule reacts with the light of the wavelength range of 250 nm - 400 nm, and shows liquid crystallinity in the temperature range of 100 degreeC - 300 degreeC.

(A) It is preferable that side chain type polymer|macromolecule has a photosensitive side chain which reacts with the light of the wavelength range of 250 nm - 400 nm.

(A) In order that side chain type polymer|macromolecule may show liquid crystallinity in the temperature range of 100 degreeC - 300 degreeC, it is preferable to have a mesogenic group.

(A) A side chain polymer|macromolecule has the side chain which has photosensitivity couple|bonded with the main chain, and can generate|occur|produce a crosslinking reaction, an isomerization reaction, or an optical Fris dislocation by sensitizing to light. Although the structure of the side chain which has photosensitivity is not specifically limited, The structure which responds to light and raise|generates a crosslinking reaction or an optical Fries dislocation is preferable, and it is more preferable to raise a crosslinking reaction. In this case, even when exposed to external stress such as heat, the realized orientation control ability can be stably maintained for a long period of time. Although the structure of the photosensitive side chain type polymer film which can express liquid crystallinity will not be specifically limited if such a characteristic is satisfy|filled, It is preferable to have a rigid mesogenic component in a side chain structure. In this case, when the side chain type polymer|macromolecule is used as a liquid crystal aligning film, stable liquid-crystal orientation can be obtained.

The polymer structure has, for example, a main chain and a side chain bonded thereto, and the side chain is a mesogen component such as a biphenyl group, a terphenyl group, a phenylcyclohexyl group, a phenylbenzoate group, and an azobenzene group; It has a structure having a photosensitive group bonded to the tip and undergoing a crosslinking reaction or isomerization reaction in response to light, a main chain and a side chain bonded thereto, and the side chain also serves as a mesogenic component, and also undergoes an optical Fris rearrangement reaction It can be set as the structure which has a phenyl benzoate group.

As a more specific example of the structure of the photosensitive side chain type polymer film which can express liquid crystallinity, Hydrocarbon, acrylate, (meth)acrylate, itaconate, fumarate, maleate, α-methylene-γ-butyrolactone , a main chain composed of at least one selected from the group consisting of radical polymerizable groups such as styrene, vinyl, maleimide, norbornene, and siloxane, and a side chain composed of at least one of the following formulas (1) to (6) It is preferable to have a structure with

[Formula 17]

In the formula, A, B, D are each independently a single bond, -O-, -CH ₂ -, -COO-, -OCO-, -CONH-, -NH-CO-, -CH=CH-CO-O - or -O-CO-CH=CH- is represented;

S is a C1-C12 alkylene group, and the hydrogen atom couple|bonded with them may be substituted by the halogen group;

T is a single bond or an alkylene group having 1 to 12 carbon atoms, and the hydrogen atom bonded thereto may be substituted with a halogen group;

Y ₁ represents a ring selected from a monovalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring and an alicyclic hydrocarbon having 5 to 8 carbon atoms, or the same or different 2 to 6 rings selected from their substituents is a group formed by bonding via a bonding group B, and the hydrogen atoms bonded thereto are each independently -COOR ₀ (wherein R ₀ represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms), -NO ₂ , - CN, -CH=C(CN) ₂ , -CH=CH-CN, a halogen group, a C1-C5 alkyl group, or a C1-C5 alkyloxy group may be substituted;

Y ₂ is a group selected from the group consisting of a divalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring, an alicyclic hydrocarbon having 5 to 8 carbon atoms, and combinations thereof, and a hydrogen atom bonded thereto is each independently -NO ₂ , -CN, -CH=C(CN) ₂ , -CH=CH-CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or an alkyloxy group having 1 to 5 carbon atoms;

R represents a hydroxy group, an alkoxy group having 1 to 6 carbon atoms, or has the same definition as _{Y 1 ;}

X is a single bond, -COO-, -OCO-, -N=N-, -CH=CH-, -C≡C-, -CH=CH-CO-O-, or -O-CO-CH=CH - and when the number of X becomes 2, X may be the same or different;

Cou represents a coumarin-6-yl group or a coumarin-7-yl group, and hydrogen atoms bonded thereto are each independently -NO ₂ , -CN, -CH=C(CN) ₂ , -CH=CH-CN, halogen group, a C1-C5 alkyl group, or a C1-C5 alkyloxy group may be substituted;

one of q1 and q2 is 1 and the other is 0;

q3 is 0 or 1;

P and Q are each independently a group selected from the group consisting of a divalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring, an alicyclic hydrocarbon having 5 to 8 carbon atoms, and combinations thereof; When is -CH=CH-CO-O-, -O-CO-CH=CH-, P or Q on the side to which -CH=CH- is bonded is an aromatic ring, and when the number of P is 2 or more, P may be the same or different, and when the number of Q becomes 2 or more, Q may be same or different;

l1 is 0 or 1;

l2 is an integer of 0 to 2;

When both l1 and l2 are 0, when T is a single bond, A also represents a single bond;

When l1 is 1, when T is a single bond, B also represents a single bond;

H and I are each independently a group selected from a divalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring, and combinations thereof.

It is good that a side chain is any 1 type of photosensitive side chain chosen from the group which consists of following formula (7) - (10).

wherein A, B, D, Y ₁ , X, Y ₂ , and R have the same definitions as above;

l represents the integer of 1-12;

m represents the integer of 0-2, m1, m2 represents the integer of 1-3;

n represents an integer of 0 to 12 (provided that when n = 0, B is a single bond).

[Formula 18]

It is good that a side chain is any 1 type of photosensitive side chain chosen from the group which consists of following formula (11)-(13).

In the formula, A, X, l, m, m1 and R have the same definitions as above.

[Formula 19]

It is good that a side chain is a photosensitive side chain represented by following formula (14) or (15).

In the formula, A, Y ₁ , l, m1 and m2 have the same definitions as above.

[Formula 20]

It is good that a side chain is a photosensitive side chain represented by following formula (16) or (17).

In the formula, A, X, l and m have the same definitions as above.

[Formula 21]

Moreover, it is good that a side chain is a photosensitive side chain represented by following formula (18) or (19).

In the formula, A, B, Y ₁ , q1, q2, m1, and m2 have the same definitions as above.

R ₁ represents a hydrogen atom, -NO ₂ , -CN, -CH=C(CN) ₂ , -CH=CH-CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or an alkyloxy group having 1 to 5 carbon atoms.

[Formula 22]

It is good that a side chain is a photosensitive side chain represented by following formula (20).

In the formula, A, Y ₁ , X, l and m have the same definitions as above.

[Formula 23]

Moreover, it is good for (A) side chain type polymer|macromolecule to have any 1 type of liquid crystalline side chain chosen from the group which consists of following formula (21)-(31).

wherein A, B, q1 and q2 have the same definitions as above;

Y ₃ is a group selected from the group consisting of a monovalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a nitrogen-containing heterocyclic ring, an alicyclic hydrocarbon having 5 to 8 carbon atoms, and combinations thereof, each hydrogen atom may be independently _{substituted with -NO 2} , -CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or an alkyloxy group having 1 to 5 carbon atoms;

R ₃ is a hydrogen atom, -NO ₂ , -CN, -CH=C(CN) ₂ , -CH=CH-CN, a halogen group, a monovalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a nitrogen-containing hetero a ring, an alicyclic hydrocarbon having 5 to 8 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms;

l represents an integer of 1 to 12, m represents an integer of 0 to 2, with the proviso that in Formulas (23) to (24), the sum of all m is 2 or more, and Formulas (25) to (26) In , the sum of all m is 1 or more, and m1, m2, and m3 each independently represent an integer of 1 to 3;

R ₂ is a hydrogen atom, —NO ₂ , —CN, a halogen group, a monovalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a nitrogen-containing heterocyclic ring, and an alicyclic hydrocarbon having 5 to 8 carbon atoms, and an alkyl group; or an alkyloxy group;

Z ₁ , Z ₂ represents a single bond, -CO-, -CH ₂ O-, -CH=N-, -CF ₂ -.

[Formula 24]

<<The manufacturing method of photosensitive side chain type polymer|macromolecule>>

The photosensitive side chain type polymer|macromolecule which can express said liquid crystallinity can be obtained by superposing|polymerizing the photoreactive side chain monomer and liquid crystalline side chain monomer which have said photosensitive side chain.

[Photoreactive Side Chain Monomer]

A photoreactive side chain monomer is a monomer which can form the polymer|macromolecule which has a photosensitive side chain in the side chain site|part of a polymer|macromolecule, when polymer|macromolecule is formed.

As a photoreactive group which a side chain has, the following structure and its derivative(s) are preferable.

[Formula 25]

As more specific examples of the photoreactive side chain monomer, hydrocarbon, (meth)acrylate, itaconate, fumarate, maleate, α-methylene-γ-butyrolactone, styrene, vinyl, maleimide, norbornene, etc. A photosensitive side chain which consists of a polymeric group comprised by at least 1 type selected from the group which consists of a radically polymerizable group and siloxane, and at least 1 type in said Formula (1)-(6) Preferably, for example, said Formula ( The photosensitive side chain which consists of at least 1 type of 7)-(10), the photosensitive side chain which consists of at least 1 type of said Formula (11)-(13), the photosensitive side chain represented by said Formula (14) or (15), It is preferable that it is a structure which has the photosensitive side chain represented by the photosensitive side chain represented by the said Formula (16) or (17), the photosensitive side chain represented by the said Formula (18) or (19), and said Formula (20).

This application is a photoreactive and/or liquid crystalline side chain monomer, It is a novel compound (1) - (11) represented by the following formulas (1) - (11); And it is represented by the following formulas (12) - (17) Compounds (12) to (17) are provided.

In the formula, R represents a hydrogen atom or a methyl group; S represents an alkylene group having 2 to 10 carbon atoms; R ¹⁰ represents Br or CN; S represents an alkylene group having 2 to 10 carbon atoms; u is 0 or 1 represents; and Py represents a 2-pyridyl group, a 3-pyridyl group or a 4-pyridyl group. In addition, v represents 1 or 2.

[Formula 26]

[Formula 27]

[Formula 28]

[Liquid crystalline side chain monomer]

A liquid crystalline side chain monomer is a monomer which polymer|macromolecule derived from the monomer expresses liquid crystallinity, and the polymer can form a mesogenic group in a side chain site|part.

As a mesogenic group which a side chain has, it is group used as mesogenic structure independently, such as biphenyl and phenyl benzoate, or it may contribute to become a mesogenic structure by hydrogen bonding of side chains like benzoic acid. As a mesogenic group which a side chain has, the following structure is preferable.

[Formula 29]

As a more specific example of a liquid crystalline side chain monomer, hydrocarbon, (meth)acrylate, itaconate, fumarate, maleate, alpha-methylene-gamma-butyrolactone, styrene, vinyl, maleimide, norbornene, etc. It is preferable that it is a structure which has a polymeric group comprised by at least 1 type chosen from the group which consists of a radically polymerizable group, and the side chain which consists of at least 1 type in said Formula (21)-(31).

(A) Side chain type polymer|macromolecule can be obtained by the polymerization reaction of the photoreactive side chain monomer which expresses the above-mentioned liquid crystallinity. Moreover, it can obtain by copolymerization of the photoreactive side chain monomer and liquid crystalline side chain monomer which do not express liquid crystallinity, or copolymerization of the photoreactive side chain monomer which expresses liquid crystallinity, and a liquid crystalline side chain monomer. Moreover, it can copolymerize with another monomer in the range which does not impair liquid crystalline expression ability.

Examples of the other monomer include an industrially available monomer capable of a radical polymerization reaction.

As a specific example of another monomer, an unsaturated carboxylic acid, an acrylic acid ester compound, a methacrylic acid ester compound, a maleimide compound, an acrylonitrile, maleic anhydride, a styrene compound, a vinyl compound, etc. are mentioned.

Specific examples of the unsaturated carboxylic acid include acrylic acid, methacrylic acid, itaconic acid, maleic acid, and fumaric acid.

Examples of the acrylic acid ester compound include methyl acrylate, ethyl acrylate, isopropyl acrylate, benzyl acrylate, naphthyl acrylate, anthryl acrylate, anthryl methyl acrylate, phenyl acrylate, 2,2, 2-trifluoroethyl acrylate, tert-butyl acrylate, cyclohexyl acrylate, isobornyl acrylate, 2-methoxyethyl acrylate, methoxytriethylene glycol acrylate, 2-ethoxyethyl acrylate, Tetrahydrofurfuryl acrylate, 3-methoxybutyl acrylate, 2-methyl-2-adamantyl acrylate, 2-propyl-2-adamantyl acrylate, 8-methyl-8-tricyclodecyl acrylate , and 8-ethyl-8-tricyclodecyl acrylate.

As a methacrylic acid ester compound, for example, methyl methacrylate, ethyl methacrylate, isopropyl methacrylate, benzyl methacrylate, naphthyl methacrylate, anthryl methacrylate, anthryl methyl methacrylate , Phenyl methacrylate, 2,2,2-trifluoroethyl methacrylate, tert-butyl methacrylate, cyclohexyl methacrylate, isobornyl methacrylate, 2-methoxyethyl methacrylate, methacrylate Toxytriethylene glycol methacrylate, 2-ethoxyethyl methacrylate, tetrahydrofurfuryl methacrylate, 3-methoxybutyl methacrylate, 2-methyl-2-adamantyl methacrylate, 2-propyl -2-adamantyl methacrylate, 8-methyl-8-tricyclodecyl methacrylate, and 8-ethyl-8-tricyclodecyl methacrylate, and the like. Cyclic ethers such as glycidyl (meth) acrylate, (3-methyl-3-oxetanyl) methyl (meth) acrylate, and (3-ethyl-3-oxetanyl) methyl (meth) acrylate A (meth)acrylate compound having a group can also be used.

Examples of the vinyl compound include vinyl ether, methyl vinyl ether, benzyl vinyl ether, 2-hydroxyethyl vinyl ether, phenyl vinyl ether, and propyl vinyl ether.

As a styrene compound, styrene, methylstyrene, chlorostyrene, bromostyrene, etc. are mentioned, for example.

As a maleimide compound, maleimide, N-methyl maleimide, N-phenyl maleimide, N-cyclohexyl maleimide, etc. are mentioned, for example.

It does not specifically limit about the manufacturing method of side chain type polymer|macromolecule of this embodiment, The general-purpose method handled industrially can be used. Specifically, it can manufacture by cationic polymerization using the vinyl group of a liquid crystalline side chain monomer or a photoreactive side chain monomer, radical polymerization, and anionic polymerization. Among these, radical polymerization is especially preferable from a viewpoint of the easiness of reaction control, etc.

As the polymerization initiator of the radical polymerization, a known compound such as a radical polymerization initiator or a reversible addition-cleavage chain transfer (RAFT) polymerization reagent can be used.

A radical thermal polymerization initiator is a compound which generate|occur|produces a radical by heating to decomposition temperature or more. As such a radical thermal polymerization initiator, for example, ketone peroxides (methyl ethyl ketone peroxide, cyclohexanone peroxide, etc.), diacyl peroxides (acetyl peroxide, benzoyl peroxide, etc.), hydroperoxides ( Hydrogen peroxide, tert-butyl hydroperoxide, cumene hydroperoxide, etc.), dialkyl peroxides (di-tert-butyl peroxide, dicumyl peroxide, dilauroyl peroxide, etc.), peroxyketals (dibutyl peroxide, etc.) oxycyclohexane, etc.), alkyl peresters (peroxyneodecanoic acid-tert-butyl ester, peroxypivalic acid-tert-butyl ester, peroxy2-ethylcyclohexanoic acid-tert-amyl ester, etc.), persulfate compounds (potassium persulfate, sodium persulfate, ammonium persulfate, etc.), azo compounds (azobisisobutyronitrile, 2,2'-di(2-hydroxyethyl) azobisisobutyronitrile, etc.) can Such a radical thermal polymerization initiator may be used individually by 1 type, or may be used in combination of 2 or more type.

A radical photoinitiator will not be specifically limited if it is a compound which starts radical polymerization by light irradiation. Examples of such a radical photopolymerization initiator include benzophenone, Michler's ketone, 4,4'-bis(diethylamino)benzophenone, xanthone, thioxanthone, isopropylxanthone, and 2,4-diethylthioxanthone. , 2-ethylanthraquinone, acetophenone, 2-hydroxy-2-methylpropiophenone, 2-hydroxy-2-methyl-4'-isopropylpropiophenone, 1-hydroxycyclohexylphenylketone, iso Propylbenzoin ether, isobutyl benzoin ether, 2,2-diethoxyacetophenone, 2,2-dimethoxy-2-phenylacetophenone, camphorquinone, benzanthrone, 2-methyl-1-[4-( Methylthio)phenyl]-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1,4-dimethylaminobenzoate ethyl, 4 -Dimethylaminobenzoic acid isoamyl, 4,4'-di(t-butylperoxycarbonyl)benzophenone, 3,4,4'-tri(t-butylperoxycarbonyl)benzophenone, 2,4, 6-trimethylbenzoyldiphenylphosphine oxide, 2-(4'-methoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(3',4'-dimethoxystyryl) reyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(2',4'-dimethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(2'-methoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4'-pentyloxystyryl)-4,6-bis(trichloromethyl) -s-triazine, 4-[pN,N-di(ethoxycarbonylmethyl)]-2,6-di(trichloromethyl)-s-triazine, 1,3-bis(trichloromethyl)- 5-(2'-chlorophenyl)-s-triazine, 1,3-bis(trichloromethyl)-5-(4'-methoxyphenyl)-s-triazine, 2-(p-dimethylaminostiazine Reyl) benzoxazole, 2-(p-dimethylaminostyryl) benzthiazole, 2-mercaptobenzothiazole, 3,3'-carbonylbis(7-diethylaminocoumarin), 2-(o- Chlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra kiss (4-ethoxycarbonylphenyl)-1,2'-biimidazole, 2,2'-bis(2,4-dichlorophenyl)-4,4',5,5'-tetraphenyl-1, 2'-biimidazole, 2,2'bis(2,4-dibromophenyl)-4, 4',5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis(2,4,6-trichlorophenyl)-4,4',5,5'-tetraphenyl -1,2'-biimidazole, 3-(2-methyl-2-dimethylaminopropionyl)carbazole, 3,6-bis(2-methyl-2-morpholinopropionyl)-9-n- dodecylcarbazole, 1-hydroxycyclohexylphenyl ketone, bis(5-2,4-cyclopentadien-1-yl)-bis(2,6-difluoro-3-(1H-pyrrole-1- yl)-phenyl) titanium, 3,3',4,4'-tetra(t-butylperoxycarbonyl)benzophenone, 3,3',4,4'-tetra(t-hexylperoxycarbonyl) Benzophenone, 3,3'-di(methoxycarbonyl)-4,4'-di(t-butylperoxycarbonyl)benzophenone, 3,4'-di(methoxycarbonyl)-4,3 '-di(t-butylperoxycarbonyl)benzophenone, 4,4'-di(methoxycarbonyl)-3,3'-di(t-butylperoxycarbonyl)benzophenone, 2-(3 -Methyl-3H-benzothiazol-2-ylidene)-1-naphthalen-2-yl-ethanone, or 2-(3-methyl-1,3-benzothiazol-2(3H)-ylidene) -1-(2-benzoyl)ethanone and the like. These compounds may be used independently and may be used in mixture of 2 or more.

The radical polymerization method is not particularly limited, and an emulsion polymerization method, a suspension polymerization method, a dispersion polymerization method, a precipitation polymerization method, a bulk polymerization method, a solution polymerization method, and the like can be used.

It will not specifically limit, if the produced|generated polymer|macromolecule melt|dissolves as an organic solvent used for the polymerization reaction of the photosensitive side chain type polymer|macromolecule which can express liquid crystallinity. The specific example is given below.

N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, N-methylcaprolactam, dimethylsulfoxide, tetramethylurea, Pyridine, dimethyl sulfone, hexamethyl sulfoxide, γ-butyrolactone, isopropyl alcohol, methoxymethylpentanol, dipentene, ethyl amyl ketone, methyl nonyl ketone, methyl ethyl ketone, methyl isoamyl ketone, methyl isopropyl Ketone, methyl cellosolve, ethyl cellosolve, methyl cellosolve acetate, ethyl cellosolve acetate, butyl carbitol, ethyl carbitol, ethylene glycol, ethylene glycol monoacetate, ethylene glycol monoisopropyl ether, ethylene glycol mono Butyl ether, propylene glycol, propylene glycol monoacetate, propylene glycol monomethyl ether, propylene glycol-tert-butyl ether, dipropylene glycol monomethyl ether, diethylene glycol, diethylene glycol monoacetate, diethylene glycol dimethyl ether, dipropylene Glycol monoacetate monomethyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monoacetate monoethyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monoacetate monopropyl ether, 3-methyl- 3-methoxybutyl acetate, tripropylene glycol methyl ether, 3-methyl-3-methoxybutanol, diisopropyl ether, ethyl isobutyl ether, diisobutylene, amyl acetate, butyl butyrate, butyl ether, diiso Butyl ketone, methylcyclohexene, propyl ether, dihexyl ether, dioxane, n-hexane, n-pentane, n-octane, diethyl ether, cyclohexanone, ethylene carbonate, propylene carbonate, methyl lactate, ethyl lactate, acetic acid Methyl, ethyl acetate, n-butyl acetate, propylene glycol monoethyl ether acetate, methyl pyruvate, ethyl pyruvate, methyl 3-methoxypropionate, methyl ethyl 3-ethoxypropionate, ethyl 3-methoxypropionate, 3-ethoxypropionic acid , 3-methoxypropionic acid, 3-methoxypropionic acid propyl, 3-methoxypropionate butyl, diglyme, 4-hydroxy-4-methyl-2-pentanone, 3-methoxy-N,N-dimethylpropanamide , 3-ethoxy-N,N-dimethylpropanamide, 3-butoxy-N,N-dimethylpropana Mead etc. are mentioned.

These organic solvents may be used independently or may be mixed and used. Moreover, even if it is a solvent which does not dissolve the produced|generated polymer|macromolecule, you may use it in the range in which the produced|generated polymer|macromolecule does not precipitate, mixing with the organic solvent mentioned above.

Moreover, in radical polymerization, since oxygen in an organic solvent becomes a cause of inhibiting a polymerization reaction, it is preferable to use the organic solvent degassed to the extent possible.

Although the polymerization temperature at the time of radical polymerization can select the arbitrary temperature of 30 degreeC - 150 degreeC, Preferably it is the range of 50 degreeC - 100 degreeC. In addition, although the reaction can be carried out at any concentration, if the concentration is too low, it becomes difficult to obtain a high molecular weight polymer, and if the concentration is too high, the viscosity of the reaction solution becomes too high and uniform stirring becomes difficult. Preferably they are 1 mass % - 50 mass %, More preferably, they are 5 mass % - 30 mass %. The reaction initial stage can be performed at high concentration, and an organic solvent can be added after that.

In the above-mentioned radical polymerization reaction, when the ratio of the radical polymerization initiator is large with respect to the monomer, the molecular weight of the obtained polymer becomes small, and when the ratio of the radical polymerization initiator is small, the molecular weight of the obtained polymer becomes large. Therefore, the ratio of the radical initiator is 0.1 mol% with respect to the monomer to be polymerized. It is preferable that it is -10 mol%. Moreover, in the case of polymerization, various monomer components, a solvent, an initiator, etc. can also be added.

[Recovery of polymer]

When collect|recovering the produced|generated polymer|macromolecule from the reaction solution of the photosensitive side chain type polymer|macromolecule which was obtained by the above-mentioned reaction and can express liquid crystallinity, the reaction solution is thrown into a poor solvent, and these polymers are should be precipitated. Examples of the poor solvent used for precipitation include methanol, acetone, hexane, heptane, butyl cellosolve, heptane, methyl ethyl ketone, methyl isobutyl ketone, ethanol, toluene, benzene, diethyl ether, methyl ethyl ether, and water. can The polymer charged and precipitated in the poor solvent can be collected by filtration, and then dried under normal pressure or reduced pressure at room temperature or by heating. Moreover, if the polymer which carried out precipitation collection|recovery is made to dissolve again in an organic solvent, and operation which carries out reprecipitation collection|recovery is repeated 2 times - 10 times, the impurity in a polymer can be decreased. Examples of the poor solvent at this time include alcohols, ketones, and hydrocarbons, and the use of three or more types of poor solvents selected from these is preferable because the efficiency of purification further increases.

The molecular weight of the (A) side chain polymer of the present invention is the weight average molecular weight measured by the GPC (Gel Permeation Chromatography) method when the strength of the obtained coating film, workability at the time of coating film formation, and the uniformity of the coating film are considered. 2000-1000000 are preferable, More preferably, it is 5000-100000.

[Preparation of polymer composition]

It is preferable that the polymer composition used for this invention is prepared as a coating liquid so that it may become suitable for formation of a liquid crystal aligning film. That is, the polymer composition used in the present invention is preferably prepared as a solution in which a resin component for forming a resin film is dissolved in an organic solvent. Here, the resin component is a resin component containing the photosensitive side chain type polymer|macromolecule which can express already demonstrated liquid crystal. In that case, as for content of a resin component, 1 mass % - 20 mass % are preferable, More preferably, they are 3 mass % - 15 mass %, Especially preferably, they are 3 mass % - 10 mass %.

The polymer composition of this embodiment WHEREIN: Although the photosensitive side chain type polymer|macromolecule which all can express the liquid crystal property mentioned above may be sufficient as the resin component mentioned above, in the range which does not impair liquid-crystal expression ability and photosensitive performance, other than them of other polymers may be mixed. In that case, content of the other polymer in a resin component is 0.5 mass % - 80 mass %, Preferably they are 1 mass % - 50 mass %.

The polymer etc. which are not the photosensitive side chain type polymer|macromolecule which consist of poly(meth)acrylate, a polyamic acid, a polyimide, etc., and can express liquid crystallinity are mentioned, for example as such another polymer.

<Crosslinkable compound having two or more specific groups per molecule>

The polymer composition used in the present invention has a crosslinkable compound having two or more specific groups per molecule.

The compound will not be specifically limited, if the polymer composition used for this invention forms a liquid crystal aligning film, if it exhibits any 1 type, 2 types, 3 types, or all of the following effects i)-iv). i) improve the film density of the liquid crystal aligning film, ii) do not move the impurities present in the liquid crystal aligning film to the liquid crystal side, iii) exhibit an improved voltage retention, and/or iv) the liquid crystal aligning film and the mutual sealing agent By increasing the action, improved adhesion is exhibited.

The amount of the compound having two or more specific groups per molecule is not particularly limited as long as the above effects are exhibited, but it is preferably 0.1 to 150 parts by mass, preferably based on 100 parts by mass of the polymer component of the polymer composition used in the present invention. is 0.1 to 100 parts by mass, more preferably 1 to 50 parts by mass.

The "specific group" of the compound having two or more specific groups per molecule is a hydroxyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an oxirane group, an epoxy group, an isocyanate group, an oxetane group, a cyclocarbonate group, It is preferably selected from the group consisting of a trialkoxysilyl group, and a polymerizable unsaturated bond group, for example, a vinyl group, a (meth)acryloyl group, and a (meth)acryloyloxy group.

Two or more groups are selected from said group, and may be the same or different.

Hereinafter, although the crosslinkable compound which has two or more specific groups per molecule is exemplified and described, it is not limited to these. Moreover, the compound may be contained in a composition by 1 type, or may be contained in combination of 2 or more types.

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 aminodiphenylene, tetra Glycidyl-m-xylenediamine, tetraglycidyl-1,3-bis(aminoethyl)cyclohexane, tetraphenyl glycidyl ether ethane, triphenyl glycidyl ether ethane, bisphenol hexafluoroacetdiglycan Cydyl ether, 1,3-bis(1-(2,3-epoxypropoxy)-1-trifluoromethyl-2,2,2-trifluoromethyl)benzene, 4,4-bis(2, 3-epoxypropoxy) octafluorobiphenyl, triglycidyl-p-aminophenol, tetraglycidyl metaxylenediamine, 2-(4-(2,3-epoxypropoxy)phenyl)-2-(4 -(1,1-bis(4-(2,3-epoxypropoxy)phenyl)ethyl)phenyl)propane, 1,3-bis(4-(1-(4-(2,3-epoxypropoxy) and phenyl)-1-(4-(1-(4-(2,3-epoxypropoxyphenyl)-1-methylethyl)phenyl)ethyl)phenoxy)-2-propanol.

As a crosslinkable compound which has an oxetane group, it is a crosslinkable compound which has at least two oxetane groups shown by a following formula [4].

[Formula 30]

It is a crosslinking|crosslinked compound specifically, shown by a following formula [4a] - a formula [4k], for example.

[Formula 31]

[Formula 32]

[Formula 33]

As a crosslinkable compound which has at least 1 sort(s) of substituent selected from the group which consists of a hydroxyl group and an alkoxyl group, For example, the amino resin which has a hydroxyl group or an alkoxyl group, for example, a melamine resin, a urea resin, a guanamine resin , glycoluril-formaldehyde resin, succinylamide-formaldehyde resin, ethyleneurea-formaldehyde resin, and the like.

As this crosslinkable compound, for example, a melamine derivative, a benzoguanamine derivative, or glycoluril in which the hydrogen atom of the amino group is substituted with a methylol group, an alkoxymethyl group, or both can be used. These melamine derivatives and benzoguanamine derivatives may exist as dimers or trimers. It is preferable that these have an average of 3 or more and 6 or less of a methylol group or an alkoxymethyl group per triazine ring.

Examples of such a melamine derivative or benzoguanamine derivative include MX-750, in which an average of 3.7 methoxymethyl groups are substituted per triazine ring, and MW-, in which an average of 5.8 methoxymethyl groups are substituted per triazine ring. 30 (above, manufactured by Sanwa Chemical), Cymel 300, 301, 303, 350, 370, 771, 325, 327, 703, 712 Methoxymethylated melamine, Cymel 235, 236, 238, 212, 253, Methoxymethylated butoxymethylated melamine such as 254, butoxymethylated melamine such as Cymel 506 and 508, carboxymethyl group-containing methoxymethylated isobutoxymethylated melamine such as Cymel 1141, Methoxymethylated ethoxymethylated benzo such as Cymel 1123 Guanamine, methoxymethylated butoxymethylated benzoguanamine such as Cymel 1123-10, butoxymethylated benzoguanamine such as Cymel 1128, carboxyl group-containing methoxymethylated ethoxymethylated benzoguanamine such as Cymel 1125-80 (above, Mitsui cyanamide make) is mentioned. Moreover, as an example of a glycoluril, a butoxymethylation glycoluril like Cymel 1170, a methylolation glycoluril like Cymel 1172, methoxymethylolation glycoluril like Powder Link 1174, etc. are mentioned.

As a benzene or phenolic compound having a hydroxyl group or an alkoxyl group, for example, 1,3,5-tris(methoxymethyl)benzene, 1,2,4-tris(isopropoxymethyl)benzene, 1,4 -bis(sec-butoxymethyl)benzene, 2, 6- dihydroxymethyl-p-tert- butylphenol, etc. are mentioned.

Moreover, as a crosslinkable compound which has at least 1 sort(s) of substituent chosen from the group which consists of a hydroxyl group and an alkoxyl group, tetraalkoxysilane etc. can also be used.

Specific examples of the compound having two or more trialkoxysilyl groups include 1,4-bis(trimethoxysilyl)benzene, 1,4-bis(triethoxysilyl)benzene, 4,4′-bis(trimethoxysilyl) Biphenyl, 4,4'-bis(triethoxysilyl)biphenyl, bis(trimethoxysilyl)ethane, bis(triethoxysilyl)ethane, bis(trimethoxysilyl)methane, bis(triethoxy Silyl)methane, bis(trimethoxysilyl)ethylene, bis(triethoxysilyl)ethylene, 1,3-bis(trimethoxysilylethyl)tetramethyldisiloxane, 1,3-bis(triethoxysilylethyl) ) Tetramethyldisiloxane, bis(triethoxysilylmethyl)amine, bis(trimethoxysilylmethyl)amine, bis(triethoxysilylpropyl)amine, bis(trimethoxysilylpropyl)amine, bis(3- Trimethoxysilylpropyl)carbonate, bis(3-triethoxysilylpropyl)carbonate, bis[(3-trimethoxysilyl)propyl]disulfide, bis[(3-triethoxysilyl)propyl]disulfide, Bis[(3-trimethoxysilyl)propyl]thiourea, bis[(3-triethoxysilyl)propyl]thiourea, bis[(3-trimethoxysilyl)propyl]urea, bis[(3-tri Ethoxysilyl)propyl]urea, 1,4-bis(trimethoxysilylmethyl)benzene, 1,4-bis(triethoxysilylmethyl)benzene, tris(trimethoxysilylpropyl)amine, tris(trie) Toxysilylpropyl)amine, 1,1,2-tris(trimethoxysilyl)ethane, 1,1,2-tris(triethoxysilyl)ethane, tris(3-trimethoxysilylpropyl)isocyanurate and compounds such as tris(3-triethoxysilylpropyl)isocyanurate.

Examples of the crosslinkable compound having a polymerizable unsaturated bond include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, and tri(meth)acryloyloxy. A crosslinkable compound having three polymerizable unsaturated groups in a molecule, such as ethoxytrimethylolpropane and glycerin polyglycidyl ether poly(meth)acrylate, furthermore, ethylene glycol di(meth)acrylate, diethylene glycol di(meth) ) acrylate, tetraethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, butylene glycol di(meth)acrylic rate, neopentyl glycol di(meth)acrylate, ethylene oxide bisphenol A type di(meth)acrylate, propylene oxide bisphenol type di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, glycerin di (meth)acrylate, pentaerythritol di(meth)acrylate, ethylene glycol diglycidyl ether di(meth)acrylate, diethylene glycol diglycidyl ether di(meth)acrylate, diglycidyl phthalate A crosslinkable compound having two polymerizable unsaturated groups in the molecule, such as ester di(meth)acrylate and neopentylglycol di(meth)acrylate hydroxypivalate, in addition to 2-hydroxyethyl(meth)acrylate, 2 -Hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 2-phenoxy-2-hydroxypropyl (meth) acrylate, 2- (meth) acryloyloxy-2-hydr Roxypropyl phthalate, 3-chloro-2-hydroxypropyl (meth) acrylate, glycerin mono (meth) acrylate, 2- (meth) acryloyloxyethyl phosphate, N-methylol (meth) acrylamide, etc. and crosslinkable compounds having one polymerizable unsaturated group in the molecule.

In addition, the compound shown by a following formula [5] can also be used.

[Formula 34]

(in formula [5], A ₁ is n-valent selected from a cyclohexyl ring, a bicyclohexyl ring, a benzene ring, a biphenyl ring, a terphenyl ring, a naphthalene ring, a fluorene ring, an anthracene ring, or a phenanthrene ring It is group, A<_2> is group chosen from a following formula [5a] or a formula [5b], and n is an integer of 1-4).

[Formula 35]

<Organic solvent>

The organic solvent used for the polymer composition used for this invention will not be specifically limited if it is an organic solvent in which a resin component is dissolved. The specific example is given below.

N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylcaprolactam, 2-pyrrolidone, N-ethylpyrrolidone, N-vinylpyrrolidone Don, dimethylsulfoxide, tetramethylurea, pyridine, dimethylsulfone, hexamethylsulfoxide, γ-butyrolactone, 3-methoxy-N,N-dimethylpropanamide, 3-ethoxy-N,N-dimethylpropane Amide, 3-butoxy-N,N-dimethylpropanamide, 1,3-dimethyl-imidazolidinone, ethyl amyl ketone, methyl nonyl ketone, methyl ethyl ketone, methyl isoamyl ketone, methyl isopropyl ketone, cyclo Hexanone, ethylene carbonate, propylene carbonate, diglyme, 4-hydroxy-4-methyl-2-pentanone, propylene glycol monoacetate, propylene glycol monomethyl ether, propylene glycol-tert-butyl ether, dipropylene glycol monomethyl Ether, diethylene glycol, diethylene glycol monoacetate, diethylene glycol dimethyl ether, dipropylene glycol monoacetate monomethyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monoacetate monoethyl ether, Dipropylene glycol monopropyl ether, dipropylene glycol monoacetate monopropyl ether, 3-methyl-3-methoxybutyl acetate, tripropylene glycol methyl ether, etc. are mentioned. These may be used independently or may be mixed and used.

The polymer composition used for this invention may contain components other than said (A), (B), and (C) component. Although the solvent and compound which improve film-thickness uniformity and surface smoothness at the time of apply|coating a polymer composition as the example, the compound etc. which improve the adhesiveness of a liquid crystal aligning film and a board|substrate are mentioned, It is not limited to this.

The following are mentioned as a specific example of the solvent (poor solvent) which improves the uniformity of a film thickness and surface smoothness.

For example, isopropyl alcohol, methoxymethylpentanol, methyl cellosolve, ethyl cellosolve, butyl cellosolve, methyl cellosolve acetate, ethyl cellosolve acetate, butyl carbitol, ethyl carbitol, ethyl Carbitol acetate, ethylene glycol, ethylene glycol monoacetate, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, propylene glycol, propylene glycol monoacetate, propylene glycol monomethyl ether, propylene glycol mono n-butyl ether, propylene glycol- tert-Butyl ether, dipropylene glycol monomethyl ether, diethylene glycol, diethylene glycol monoacetate, diethylene glycol dimethyl ether, dipropylene glycol monoacetate monomethyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether , Dipropylene glycol monoacetate monoethyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monoacetate monopropyl ether, 3-methyl-3-methoxybutyl acetate, tripropylene glycol methyl ether, 3-methyl-3-methyl Toxybutanol, diisopropyl ether, ethyl isobutyl ether, diisobutylene, amyl acetate, butyl butyrate, butyl ether, diisobutyl ketone, methylcyclohexene, propyl ether, dihexyl ether, 1-hexanol, n -Hexane, n-pentane, n-octane, diethyl ether, methyl lactate, ethyl lactate, methyl acetate, ethyl acetate, n-butyl acetate, propylene glycol monoethyl ether, methyl pyruvate, ethyl pyruvate, 3-methoxypropionic acid Methyl, 3-ethoxypropionate methylethyl, 3-methoxyethylpropionate, 3-ethoxypropionic acid, 3-methoxypropionic acid, 3-methoxypropionic acid propyl, 3-methoxybutylpropionate, 1-methoxy-2- Propanol, 1-ethoxy-2-propanol, 1-butoxy-2-propanol, 1-phenoxy-2-propanol, propylene glycol monoacetate, propylene glycol diacetate, propylene glycol-1-monomethyl ether-2- Acetate, propylene glycol-1-monoethyl ether-2-acetate, dipropylene glycol, 2-(2-ethoxypropoxy)propanol, lactic acid methyl ester, lactic acid ethyl ester, lactic acid n-propyl ester, lactic acid n-butyl ester , lactic acid isoamyl ester, etc. solvents having a low surface tension of

These poor solvents may be used by one type or in mixture of multiple types. When using the solvent as mentioned above, it is preferable that it is 5 mass % - 80 mass % of the whole solvent so that the solubility of the whole solvent contained in a polymer composition may not be reduced remarkably, More preferably, 20 They are mass % - 60 mass %.

As a compound which improves the uniformity of a film thickness and surface smoothness, a fluorine-type surfactant, silicone type surfactant, nonionic surfactant, etc. are mentioned.

More specifically, for example, FTOP (registered trademark) 301, EF303, EF352 (manufactured by Tochem Products), Megapack (registered trademark) F171, F173, R-30 (manufactured by DIC), Florard FC430, FC431 (manufactured by Sumitomo 3M), AsahiGuard (registered trademark), AG710 (manufactured by Asahi Glass, Inc.), Sufflon (registered trademark) S-382, SC101, SC102, SC103, SC104, SC105, SC106 (manufactured by AGC Seimi Chemical) ) and the like. To [ the usage ratio of these surfactant / 100 mass parts of resin components contained in a polymer composition ], Preferably they are 0.01 mass part - 2 mass parts, More preferably, they are 0.01 mass part - 1 mass part.

As a specific example of the compound which improves the adhesiveness of a liquid crystal aligning film and a board|substrate, the functional silane containing compound etc. which are shown next are mentioned.

For example, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 2-aminopropyltrimethoxysilane, 2-aminopropyltriethoxysilane, N-(2-aminoethyl)-3 -Aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, 3-ureidopropyltrimethoxysilane, 3-ureidopropyltriethoxysilane, N-ethoxy Carbonyl-3-aminopropyltrimethoxysilane, N-ethoxycarbonyl-3-aminopropyltriethoxysilane, N-triethoxysilylpropyltriethylenetriamine, N-trimethoxysilylpropyltriethylenetri Amine, 10-trimethoxysilyl-1,4,7-triazadecane, 10-triethoxysilyl-1,4,7-triazadecane, 9-trimethoxysilyl-3,6-diazanonyl Acetate, 9-triethoxysilyl-3,6-diazanonyl acetate, N-benzyl-3-aminopropyltrimethoxysilane, N-benzyl-3-aminopropyltriethoxysilane, N-phenyl-3- Aminopropyltrimethoxysilane, N-phenyl-3-aminopropyltriethoxysilane, N-bis(oxyethylene)-3-aminopropyltrimethoxysilane, N-bis(oxyethylene)-3-aminopropyltri Ethoxysilane etc. are mentioned.

Moreover, in addition to the improvement of the adhesiveness of a board|substrate and a liquid crystal aligning film, for the purpose of preventing the fall of the electrical property by the backlight when a liquid crystal display element is comprised, etc., the additive of the following phenoplast type and an epoxy group containing compound is a polymer composition You may contain it in. Although a specific phenoplast type additive is shown below, it is not limited to this structure.

[Formula 36]

Specific examples of the epoxy group-containing compound include ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, and neopentyl. Glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, glycerin diglycidyl ether, 2,2-dibromoneopentyl glycol diglycidyl ether, 1,3,5,6- Tetraglycidyl-2,4-hexanediol, N,N,N',N'-tetraglycidyl-m-xylenediamine, 1,3-bis(N,N-diglycidylaminomethyl) Cyclohexane, N,N,N',N'-tetraglycidyl-4,4'-diaminodiphenylmethane, etc. are illustrated.

When using the compound which improves adhesiveness with a board|substrate, it is preferable that the usage-amount is 0.1 mass part - 30 mass parts with respect to 100 mass parts of the resin component contained in a polymer composition, More preferably, 1 mass part - 20 mass parts is wealth When the usage-amount is less than 0.1 mass part, the effect of an adhesive improvement cannot be anticipated, and when it increases more than 30 mass parts, the orientation of a liquid crystal may worsen.

A photosensitizer can also be used as an additive. Colorless sensitizers and triplet sensitizers are preferred.

Examples of the photosensitizer include an aromatic nitro compound, coumarin (7-diethylamino-4-methylcoumarin, 7-hydroxy4-methylcoumarin), ketocoumarin, carbonylbiscoumarin, aromatic 2-hydroxyketone, and amino. substituted, aromatic 2-hydroxyketone (2-hydroxybenzophenone, mono- or di-p-(dimethylamino)-2-hydroxybenzophenone), acetophenone, anthraquinone, xanthone, thioxanthone, Benzanthrone, thiazoline (2-benzoylmethylene-3-methyl-β-naphthothiazoline, 2-(β-naphthoylmethylene)-3-methylbenzothiazoline, 2-(α-naphthoylmethylene)-3 -Methylbenzothiazoline, 2-(4-biphenoylmethylene)-3-methylbenzothiazoline, 2-(β-naphthoylmethylene)-3-methyl-β-naphthothiazoline, 2-(4-biphenoyl Methylene)-3-methyl-β-naphthothiazoline, 2-(p-fluorobenzoylmethylene)-3-methyl-β-naphthothiazoline), oxazoline (2-benzoylmethylene-3-methyl-β-naph Tooxazoline, 2-(β-naphthoylmethylene)-3-methylbenzoxazoline, 2-(α-naphthoylmethylene)-3-methylbenzoxazoline, 2-(4-biphenoylmethylene)-3- Methylbenzoxazoline, 2-(β-naphthoylmethylene)-3-methyl-β-naphthooxazoline, 2-(4-biphenoylmethylene)-3-methyl-β-naphthooxazoline, 2-( p-fluorobenzoylmethylene)-3-methyl-β-naphthooxazoline), benzothiazole, nitroaniline (m- or p-nitroaniline, 2,4,6-trinitroaniline) or nitroacenaphthene (5- nitroacenaphthene), (2-[(m-hydroxy-p-methoxy) styryl] benzothiazole, benzoin alkyl ether, N-alkylated phthalone, acetophenone ketal (2,2-dimethoxyphenyl ethanone) ), naphthalene, anthracene (2-naphthalenemethanol, 2-naphthalenecarboxylic acid, 9-anthracenemethanol, and 9-anthracenecarboxylic acid), benzopyran, azoindolizine, merocumarin, and the like.

Preferred are aromatic 2-hydroxyketone (benzophenone), coumarin, ketocoumarin, carbonylbiscoumarin, acetophenone, anthraquinone, xanthone, thioxanthone, and acetophenoneketal.

In the polymer composition, if it is the range in which the effect of this invention is not impaired other than what was mentioned above, for the purpose of changing electrical properties, such as dielectric constant and electroconductivity of a liquid crystal aligning film, when it is set as a dielectric material and an electrically-conductive material, furthermore, a liquid crystal aligning film You may add a crosslinking|crosslinked compound for the purpose of raising the hardness and density of the film|membrane.

The method of apply|coating the above-mentioned polymer composition on the board|substrate which has the electrically conductive film for lateral electric field drive is not specifically limited.

As for the coating method, industrially, the method of performing by screen printing, offset printing, flexographic printing, the inkjet method, etc. is common. As another coating method, there exist a dip method, the roll coater method, the slit coater method, the spinner method (rotary coating method), the spray method, etc., You may use these according to the objective.

After apply|coating the polymer composition on the board|substrate which has the electrically conductive film for transverse electric field drive, 50-200 degreeC, preferably 50-150 by heating means, such as a hotplate, a heat circulation type oven, or an IR (infrared) type oven. A coating film can be obtained by evaporating the solvent at °C. It is preferable that the drying temperature at this time is lower than the liquid crystal phase expression temperature of side chain type polymer|macromolecule.

When the thickness of the coating film is too thick, it is disadvantageous in terms of power consumption of the liquid crystal display element, and when it is too thin, the reliability of the liquid crystal display element may decrease. Therefore, preferably 5 nm to 300 nm, more preferably 10 nm ∼150 nm.

Moreover, it is also possible to set the process of cooling the board|substrate with a coating film to room temperature after the [I] process before the subsequent [II] process.

<Process [II]>

In process [II], the ultraviolet-ray which polarized to the coating film obtained by process [I] is irradiated. When irradiating the polarized ultraviolet-ray to the film surface of a coating film, the polarized ultraviolet-ray is irradiated through a polarizing plate from a fixed direction with respect to a board|substrate. As the ultraviolet rays to be used, ultraviolet rays having a wavelength of 100 nm to 400 nm can be used. Preferably, an optimal wavelength is selected through a filter etc. according to the kind of coating film to be used. And, for example, in order to selectively cause a photocrosslinking reaction, ultraviolet rays having a wavelength of 290 nm to 400 nm may be selected and used. As the ultraviolet rays, for example, light emitted from a high-pressure mercury lamp can be used.

The irradiation amount of polarized ultraviolet rays depends on the coating film used. The irradiation amount is the amount of polarized ultraviolet light that realizes the maximum value of ΔA (hereinafter also referred to as ΔAmax), which is the difference between the ultraviolet absorbance in a direction parallel to the polarization direction of the polarized ultraviolet light and the ultraviolet absorbance in the perpendicular direction in the coating film. It is preferable to set it within the range of 1 % - 70 %, and it is more preferable to set it within the range of 1 % - 50 %.

<Process [III]>

In process [III], the coating film to which the ultraviolet-ray polarized in process [II] was irradiated is heated. By heating, orientation control ability can be provided to a coating film.

Heating may use a heating means, such as a hot plate, a heat circulation type oven, or an IR (infrared) type oven. The heating temperature can be determined in consideration of the temperature at which the liquid crystallinity of the coating film to be used is expressed.

It is preferable that heating temperature exists in the temperature range of the temperature (henceforth liquid crystal expression temperature) at which side chain type polymer|macromolecule expresses liquid crystallinity. In the case of a thin film surface like a coating film, it is expected that the liquid crystal expression temperature of the coating film surface is lower than the liquid crystal expression temperature at the time of observing the photosensitive side chain type polymer|macromolecule which can express liquid crystal in bulk. For this reason, it is more preferable that heating temperature exists in the temperature range of the liquid-crystal expression temperature of the coating-film surface. That is, the temperature range of the heating temperature after irradiation with polarized ultraviolet light is 10 ° C lower than the lower limit of the temperature range of the liquid crystal expression temperature of the side chain type polymer to be used as the lower limit, and the upper limit is the temperature 10 ° C lower than the upper limit of the liquid crystal temperature range. It is preferable that it is a temperature in the range made into When the heating temperature is lower than the above temperature range, the effect of amplifying the anisotropy by heat in the coating film tends to be insufficient, and when the heating temperature is too high than the above temperature range, the coating film state is in an isotropic liquid state (isotropic phase). ), and in this case, it may be difficult to reorient in one direction due to self-organization.

In addition, the liquid crystal expression temperature is above the glass transition temperature (Tg) at which the side chain polymer or coating film surface undergoes a phase transition from the solid phase to the liquid crystal phase, and isotropic phase transition that causes a phase transition from the liquid crystal phase to the isotropic phase (isotropic phase) Temperature (Tiso) refers to the temperature below the temperature.

The thickness of the coating film formed after heating is preferably 5 nm to 300 nm, more preferably 50 nm to 150 nm for the same reason described in step [I].

By having the above process, in the manufacturing method of this invention, highly efficient and anisotropic introduction to a coating film can be implement|achieved. And the board|substrate in which the liquid crystal aligning film was formed can be manufactured with high efficiency.

<Process [IV]>

[IV] The process has a conductive film obtained in [I'] - [III'] similarly to the board|substrate (1st board|substrate) which has a liquid crystal aligning film on the electrically conductive film for lateral electric field drive obtained by [III]. A step of arranging a substrate (second substrate) provided with a liquid crystal aligning film that does not have a liquid crystal aligning film therebetween through a liquid crystal so that both liquid crystal aligning films face each other, producing a liquid crystal cell by a known method, and producing a transverse electric field driving type liquid crystal display element to be. In addition, in step [I'] to [III'], in step [I], instead of the substrate having the conductive film for lateral electric field drive, a substrate not having the lateral electric field drive film was used, and the process [ It can carry out similarly to I]-[III]. Since the only difference between the steps [I] to [III] and the steps [I'] to [III'] is the presence or absence of the above-described conductive film, the description of the steps [I'] to [III'] is omitted.

To give an example of production of a liquid crystal cell or a liquid crystal display element, prepare the above-mentioned first and second substrates, spread a spacer on the liquid crystal aligning film of one substrate, make the liquid crystal aligning film surface inside, and A method of bonding one side of the substrate together and injecting a liquid crystal under reduced pressure to seal, or after dropping a liquid crystal on the surface of the liquid crystal aligning film in which the spacer is sprayed, the method of bonding the substrates together and sealing can be exemplified. have. In this case, it is preferable to use a substrate having an electrode having a structure similar to that of a comb for lateral electric field driving as the substrate on one side. The diameter of the spacer at this time is preferably 1 µm to 30 µm, more preferably 2 µm to 10 µm. The diameter of this spacer determines the distance between the pair of substrates holding the liquid crystal layer, that is, the thickness of the liquid crystal layer.

In the manufacturing method of the board|substrate with a coating film of this invention, after apply|coating a polymer composition on a board|substrate to form a coating film, polarized ultraviolet-ray is irradiated. Next, by heating, highly efficient anisotropic introduction|transduction with respect to a side chain type polymer film is implement|achieved, and the board|substrate with the liquid crystal aligning film provided with the orientation control ability of a liquid crystal is manufactured.

In the coating film used for this invention, highly efficient anisotropic introduction to a coating film is implement|achieved using the principle of molecular reorientation caused by the self-organization based on the photoreaction of a side chain and liquid crystallinity. In the production method of the present invention, in the case of a structure having a photocrosslinkable group as a photoreactive group in the side chain polymer, a coating film is formed on the substrate using the side chain polymer, then irradiated with polarized ultraviolet light, and then, After heating, a liquid crystal display element is manufactured.

Hereinafter, embodiment using side chain type polymer|macromolecule of the structure which has group which raise|generates an optical Fris rearrangement group or isomerization as a 1st form and photoreactive group for embodiment using the side chain type polymer|macromolecule of the structure which has a photocrosslinkable group as a photoreactive group will be described as a second form.

BRIEF DESCRIPTION OF THE DRAWINGS In the 1st aspect in this invention, one which demonstrates typically the anisotropic introduction|transduction process in the manufacturing method of the liquid crystal aligning film using the side chain type polymer|macromolecule of the structure which has a photocrosslinkable group as a photoreactive group. is an example drawing of Fig. 1 (a) is a diagram schematically showing the state of the side chain polymer film before polarized light irradiation, and Fig. 1 (b) is a diagram schematically showing the state of the side chain polymer film after polarized light irradiation, Fig. 1 (c) ) is a diagram schematically showing the state of the side chain-type polymer film after heating, especially when the introduced anisotropy is small, that is, in the first aspect of the present invention, the amount of ultraviolet irradiation in step [II] maximizes ΔA It is a schematic diagram at the time of being in the range of 1% - 15% of ultraviolet irradiation amount.

It is one which explains typically the anisotropic introduction|transduction process in the manufacturing method of the liquid crystal aligning film using the side chain type polymer|macromolecule of the structure which has a photocrosslinkable group as a photoreactive group in 1st form in this invention is an example drawing of Fig. 2 (a) is a diagram schematically showing the state of the side chain polymer film before polarized light irradiation, and Fig. 2 (b) is a diagram schematically showing the state of the side chain polymer film after polarized light irradiation, Fig. 2 (c) ) is a diagram schematically showing the state of the side chain type polymer film after heating, especially when the introduced anisotropy is large, that is, in the first aspect of the present invention, the amount of ultraviolet irradiation in step [II] maximizes ΔA It is a schematic diagram at the time of being in the range of 15% - 70% of ultraviolet irradiation amount.

It is a 2nd aspect in this invention. WHEREIN: The liquid crystal aligning film using the side chain type polymer|macromolecule of the structure which has a photoisomerization group and an optical Fries potential group represented by Formula (18) mentioned above as a photoreactive group as a photoreactive group It is a figure of one example which schematically demonstrates the anisotropic introduction|transduction process in a manufacturing method. Fig. 3 (a) is a diagram schematically showing the state of the side chain polymer film before polarized light irradiation, and Fig. 3 (b) is a diagram schematically showing the state of the side chain polymer film after polarized light irradiation, Fig. 3 (c) ) is a diagram schematically showing the state of the side chain-type polymer film after heating, especially when the introduced anisotropy is small, that is, in the second aspect of the present invention, the amount of ultraviolet irradiation in step [II] maximizes ΔA It is a schematic diagram in case it exists in 1% - 70% of range of ultraviolet irradiation amount.

4 : in the manufacturing method of the liquid crystal aligning film using the side chain type polymer|macromolecule of the structure which has an optical Fries potential group represented by Formula (19) mentioned above as a photoreactive group as a photoreactive group in the 2nd aspect in this invention It is a figure of one example which schematically demonstrates the anisotropic introduction|transduction process. Fig. 4 (a) is a diagram schematically showing the state of the side chain polymer film before polarized light irradiation, and Fig. 4 (b) is a diagram schematically showing the state of the side chain polymer film after polarized light irradiation, Fig. 4 (c) ) is a diagram schematically showing the state of the side chain polymer film after heating, especially when the introduced anisotropy is large, that is, in the second aspect of the present invention, the amount of ultraviolet irradiation in step [II] maximizes ΔA It is a schematic diagram in case it exists in 1% - 70% of range of ultraviolet irradiation amount.

In the first aspect of the present invention, in the anisotropic introduction treatment to the coating film, when the ultraviolet irradiation amount in step [II] is within the range of 1% to 15% of the ultraviolet irradiation amount for maximizing ΔA, first, A coating film 1 is formed on the substrate. As shown to Fig.1 (a), in the coating film 1 formed on the board|substrate, it has the structure by which the side chain 2 is arrange|positioned at random. According to the random arrangement|sequence of the side chain 2 of the coating film 1, the mesogenic component of the side chain 2 and the photosensitive group are orientated at random, and the coating film 1 is isotropic.

In the first aspect of the present invention, in the anisotropic introduction treatment to the coating film, when the ultraviolet irradiation amount in step [II] is within the range of 15% to 70% of the ultraviolet irradiation amount for maximizing ΔA, first, A coating film 3 is formed on the substrate. As shown to Fig.2 (a), in the coating film 3 formed on the board|substrate, it has the structure by which the side chain 4 is arrange|positioned at random. According to the random arrangement|sequence of the side chain 4 of the coating film 3, the mesogenic component of the side chain 4 and the photosensitive group are orientated at random, and the coating film 2 is isotropic.

2nd aspect in this invention WHEREIN: Liquid crystal using side chain type polymer|macromolecule of the structure which has a photoisomerization group and an optical Fries potential group represented by Formula (18) mentioned above by the anisotropic introduction|transduction process with respect to a coating film. In the case of using an alignment film, when the ultraviolet irradiation amount of the [II] step is within the range of 1% to 70% of the ultraviolet irradiation amount that maximizes ΔA, the coating film 5 is first formed on the substrate. As shown to Fig.3 (a), in the coating film 5 formed on the board|substrate, it has the structure in which the side chain 6 is arrange|positioned at random. According to the random arrangement of the side chain 6 of the coating film 5, the mesogenic component and the photosensitive group of the side chain 6 are orientated at random, and the side chain type polymer film 5 is isotropic.

2nd aspect in this invention WHEREIN: In the anisotropic introduction|transduction process with respect to a coating film, when using the liquid crystal aligning film using the side chain type polymer|macromolecule of the structure which has an optical Fris potential group represented by Formula (19) mentioned above, WHEREIN: When the ultraviolet irradiation amount of the [II] process is in the range of 1% - 70% of the ultraviolet irradiation amount which maximizes ΔA, first, the coating film 7 is formed on the substrate. As shown to Fig.4 (a), in the coating film 7 formed on the board|substrate, it has the structure in which the side chain 8 is arrange|positioned at random. According to the random arrangement|sequence of the side chain 8 of the coating film 7, the mesogenic component of the side chain 8 and the photosensitive group are orientated at random, and the coating film 7 is isotropic.

In the first aspect of the present embodiment, when the ultraviolet irradiation amount in the step [II] is within the range of 1% to 15% of the ultraviolet irradiation amount for maximizing ΔA, the ultraviolet ray polarized with respect to the isotropic coating film 1 investigate Then, as shown in Fig. 1(b), the photosensitive group of the side chain 2a having a photosensitive group among the side chains 2 arranged in a direction parallel to the polarization direction of ultraviolet rays preferentially undergoes a photoreaction such as a dimerization reaction. causes As a result, the density of the side chain 2a which performed photoreaction becomes slightly high in the polarization direction of an irradiation ultraviolet-ray, and very small anisotropy is provided to the coating film 1 as a result.

In the first aspect of the present embodiment, when the ultraviolet irradiation amount in the step [II] is in the range of 15% to 70% of the ultraviolet irradiation amount that maximizes ΔA, the ultraviolet ray polarized with respect to the isotropic coating film 3 investigate Then, as shown in Fig. 2(b), the photosensitive group of the side chain 4a having a photosensitive group among the side chains 4 arranged in a direction parallel to the polarization direction of ultraviolet rays preferentially undergoes a photoreaction such as a dimerization reaction. causes As a result, the density of the side chain 4a which carried out the photoreaction becomes high in the polarization direction of an irradiation ultraviolet-ray, and small anisotropy is provided to the coating film 3 as a result.

In the 2nd aspect of this embodiment, using the liquid crystal aligning film using the side chain type polymer|macromolecule of a structure which has a photoisomerization group and a photoisomerization group and a photo Fris potential group represented by Formula (18) mentioned above, the ultraviolet irradiation amount of a [II] process When it exists in 1% - 70% of the range of the ultraviolet irradiation amount which maximizes (DELTA)A WHEREIN: With respect to this isotropic coating film 5, the polarized ultraviolet-ray is irradiated. Then, as shown in Fig. 3(b), the photosensitive group of the side chain 6a having a photosensitive group among the side chains 6 arranged in a direction parallel to the polarization direction of ultraviolet rays preferentially undergoes a photoreaction such as an optical Fleece dislocation. causes As a result, the density of the side chain 6a which performed photoreaction becomes slightly high in the polarization direction of an irradiation ultraviolet-ray, and very small anisotropy is provided to the coating film 5 as a result.

In the 2nd aspect of this embodiment, the ultraviolet irradiation amount of the [II] process maximizes ΔA using a coating film using a side chain type polymer having a structure having an optical Fris potential group, which is represented by the above formula (19). When it exists in the range of 1% - 70% of ultraviolet irradiation amount WHEREIN: With respect to this isotropic coating film 7, the polarized ultraviolet-ray is irradiated. Then, as shown in Fig. 4(b), the photosensitive group of the side chain 8a having a photosensitive group among the side chains 8 arranged in a direction parallel to the polarization direction of ultraviolet rays preferentially undergoes a photoreaction such as an optical fleece dislocation. causes As a result, the density of the side chain 8a which carried out the photoreaction becomes high in the polarization direction of an irradiation ultraviolet-ray, and small anisotropy is provided to the coating film 7 as a result.

Next, in the first embodiment of the present embodiment, when the amount of ultraviolet irradiation in step [II] is within the range of 1% to 15% of the ultraviolet irradiation amount that maximizes ΔA, the coating film 1 after polarized light irradiation is heated, liquid crystal state. Then, as shown in FIG.1(c), in the coating film 1, the quantity of the crosslinking reaction which arose differs between the direction parallel to the polarization direction of an irradiation ultraviolet-ray, and a direction perpendicular|vertical. In this case, since the amount of the crosslinking reaction generated in the direction parallel to the polarization direction of the irradiated ultraviolet light is very small, this crosslinking reaction site functions as a plasticizer. Therefore, the liquid crystallinity of the polarization direction of an irradiation ultraviolet-ray and the perpendicular|vertical direction becomes higher than the liquid crystallinity of a parallel direction, the side chain 2 which self-organizes in the direction parallel to the polarization direction of an irradiation ultraviolet-ray, and contains a mesogenic component is reorientated do. As a result, the very small anisotropy of the coating film 1 caused by the photocrosslinking reaction is amplified by heat, and greater anisotropy is imparted to the coating film 1 .

Similarly, in the first aspect of the present embodiment, when the ultraviolet irradiation amount in the step [II] is within the range of 15% to 70% of the ultraviolet irradiation amount that maximizes ΔA, the coating film 3 after polarized light irradiation is heated, liquid crystal state. Then, as shown to FIG.2(c), in the side chain type polymer film 3, the quantity of the crosslinking reaction which arose differs between the direction parallel to the polarization direction of an irradiation ultraviolet-ray, and the perpendicular|vertical direction. Therefore, it self-organizes in the direction parallel to the polarization direction of an irradiation ultraviolet-ray, and the side chain 4 containing a mesogenic component is reoriented. As a result, the small anisotropy of the coating film 3 caused by the photocrosslinking reaction is amplified by heat, and greater anisotropy is imparted to the coating film 3 .

Similarly, in the 2nd aspect of this embodiment, using the coating film using the side chain type polymer|macromolecule of the structure which has a photoisomerization group and the above-mentioned Formula (18), which has an optical Fries potential group, the ultraviolet irradiation amount of the [II] process When it exists in 1% - 70% of the range of the ultraviolet irradiation amount which maximizes this (DELTA)A WHEREIN: The coating film 5 after polarized light irradiation is heated and it is set as a liquid-crystal state. Then, as shown in FIG.3(c), in the coating film 5, the quantity of the optical Fries dislocation reaction which arose differs between the direction parallel to the polarization direction of an irradiation ultraviolet-ray, and a direction perpendicular|vertical. In this case, since the liquid crystal orientation force of the optical fleece potential body generated in the direction perpendicular to the polarization direction of the irradiated ultraviolet ray is stronger than the liquid crystal orientation force of the side chain before the reaction, it self-organizes in a direction perpendicular to the polarization direction of the irradiated ultraviolet ray to form a mesogenic component. The side chain (6) containing As a result, the very small anisotropy of the coating film 5 caused by the optical Fris dislocation reaction is amplified by heat, and a greater anisotropy is imparted to the coating film 5 .

Similarly, in the 2nd aspect of this embodiment, using the coating film using the side chain type polymer|macromolecule of the structure which has an optical Fries potential group represented by Formula (19) mentioned above by the 2nd aspect, the ultraviolet irradiation amount of the [II] process maximizes ΔA When it exists in 1 % - 70% of the range of the ultraviolet irradiation amount used as polarization|polarized-light irradiation, the coating film 7 after polarized light irradiation is heated and it is set as a liquid-crystal state. Then, as shown in FIG.4(c), in the side chain type polymer film 7, the quantity of the generated optical Fries dislocation reaction differs between the direction parallel to the polarization direction of an irradiation ultraviolet-ray, and the perpendicular|vertical direction. Since the anchoring force of the optical fleece dislocation body 8 (a) is stronger than that of the side chain 8 before dislocation, when a certain amount or more of the optical fleece dislocation body is generated, it self-organizes in a direction parallel to the polarization direction of the irradiated ultraviolet light to form a mesogenic component The side chain (8) containing As a result, the small anisotropy of the coating film 7 caused by the optical Fris dislocation reaction is amplified by heat, and greater anisotropy is imparted to the coating film 7 .

Therefore, the coating film used for the method of this invention can be set as the liquid crystal aligning film excellent in orientation control ability by introducing anisotropy with high efficiency by performing irradiation of the polarized ultraviolet-ray with respect to a coating film, and heat processing sequentially.

And in the coating film used for the method of this invention, the irradiation amount of the ultraviolet-ray which polarized with respect to a coating film, and the heating temperature in heat processing are optimized. Thereby, highly efficient and anisotropic introduction|transduction to a coating film can be implement|achieved.

The amount of polarized ultraviolet light that is optimal for the introduction of highly efficient anisotropy into the coating film used in the present invention is polarized ultraviolet light that optimizes the amount of the photosensitive group in the coating film for a photocrosslinking reaction, a photoisomerization reaction, or an optical Fris dislocation reaction. corresponding to the dose of As a result of irradiating the ultraviolet-ray which polarized with respect to the coating film used for this invention, when there are few photosensitive groups of the side chain which a photocrosslinking reaction, a photoisomerization reaction, or an optical Fries rearrangement reaction, it will not become a sufficient photoreaction amount. In that case, even if it heats after that, sufficient self-organization does not advance. On the other hand, in the coating film used in the present invention, when polarized ultraviolet rays are irradiated with respect to the structure having a photocrosslinkable group, when the photosensitive groups of the side chains to be crosslinked become excessive, the crosslinking reaction between the side chains will proceed too much. In that case, the obtained film|membrane becomes rigid, and it may interfere with advancing of the self-organization by subsequent heating. In addition, in the coating film used in the present invention, when polarized ultraviolet rays are irradiated with respect to a structure having an optical Fris dislocation group, when the photosensitive groups of the side chain reacting with an optical Fries potential group become excessive, the liquid crystallinity of the coating film will decrease too much. . In that case, the liquid crystallinity of the film|membrane obtained also falls, and it may become a hindrance of advancing of the self-assembly by subsequent heating. In addition, when irradiating a polarized ultraviolet ray to a structure having an optical Fris dislocation group, if the irradiation amount of ultraviolet ray is too large, the side chain polymer is photodecomposed, and there is a case where the progress of self-organization by subsequent heating is hindered. have.

Therefore, in the coating film used in the present invention, the optimal amount in which the photosensitive group of the side chain undergoes a photocrosslinking reaction, a photoisomerization reaction, or an optical Fris potential reaction by irradiation of polarized ultraviolet light is the amount of the photosensitive group of the side chain type polymer film. It is preferable to set it as 0.1 mol% - 40 mol%, and it is more preferable to set it as 0.1 mol% - 20 mol%. By making the quantity of the photosensitive group of the side chain which photoreacts into such a range, self-organization in subsequent heat processing advances efficiently, and highly efficient anisotropic formation in a film|membrane is attained.

In the coating film used for the method of this invention, by optimization of the irradiation amount of the polarized ultraviolet-ray, the amount of the photocrosslinking reaction and photoisomerization reaction of the photosensitive group in the side chain of a side chain type polymer film, or an optical Fris rearrangement reaction to optimize And the anisotropic introduction|transduction with respect to the coating film used for this invention which is high efficiency and is combined with subsequent heat processing is implement|achieved. In that case, about the quantity of a preferable polarization|polarized-light ultraviolet-ray, it is possible to implement based on evaluation of the ultraviolet absorption of the coating film used for this invention.

That is, about the coating film used for this invention, the ultraviolet absorption of the direction parallel to the polarization direction of the polarized ultraviolet-ray after polarized-ultraviolet irradiation and the ultraviolet absorption of the perpendicular direction are respectively measured. From the measurement result of ultraviolet absorption, ΔA, which is the difference between the ultraviolet absorbance in the direction parallel to the polarization direction of the polarized ultraviolet rays and the ultraviolet absorbance in the perpendicular direction, in the coating film is evaluated. Then, the maximum value (ΔAmax) of ΔA realized in the coating film used in the present invention and the amount of irradiation of polarized ultraviolet rays that realize it are calculated. In the manufacturing method of this invention, on the basis of the polarization|polarized-light ultraviolet irradiation amount which implement|achieves this (DELTA)Amax, the amount of the polarized ultraviolet-ray of the preferable quantity irradiated in manufacture of a liquid crystal aligning film can be determined.

In the manufacturing method of this invention, it is preferable to make the irradiation amount of the polarized ultraviolet-ray with respect to the coating film used for this invention into 1 % - 70% of the amount of the polarization|polarized-light ultraviolet-ray which implement|achieves ΔAmax, and it is 1% - 50% It is more preferable to set it within the range of The coating film used for this invention WHEREIN: The irradiation amount of the polarized-light ultraviolet-ray within the range of 1% - 50% of the quantity of the polarization|polarized-light ultraviolet-ray which implement|achieves ΔAmax is 0.1 mol% - 20 mol of the whole photosensitive group which the side chain type polymer film has % corresponds to the quantity of the polarization|polarized-light ultraviolet-ray which carries out a photocrosslinking reaction.

From the above, in the manufacturing method of this invention, in order to implement|achieve highly efficient anisotropic introduction with respect to a coating film, it is good to determine the preferable heating temperature as mentioned above on the basis of the liquid crystal temperature range of the side chain type polymer|macromolecule as a reference. . Therefore, for example, when the liquid crystal temperature range of side chain type polymer|macromolecule used for this invention is 100 degreeC - 200 degreeC, it is preferable to make heating temperature after polarization|polarized-light ultraviolet irradiation into 90 degreeC - 190 degreeC. By doing in this way, larger anisotropy is provided in the coating film used for this invention.

By doing so, the liquid crystal display device provided by the present invention exhibits high reliability against external stress such as light or heat.

As described above, the substrate for a transverse electric field driving type liquid crystal display element manufactured by the method of the present invention or a transverse electric field driving type liquid crystal display element having the substrate is excellent in reliability, and is suitable for a large-screen, high-definition liquid crystal television, etc. Available.

Hereinafter, although this invention is demonstrated using an Example, this invention is not limited to the Example.

Example

The methacrylic monomers MA1 and MA2 used in the Examples are shown below.

In addition, MA1 and MA2 were synthesize|combined as follows, respectively. That is, MA1 was synthesize|combined by the synthesis method described in patent document (WO2011-084546). MA2 was synthesized by the synthesis method described in the patent document (Unexamined-Japanese-Patent No. 9-118717).

[Formula 37]

The crosslinking agents T1-T14 used in the Example are shown below.

In addition, T1-T14 were synthesize|combined by the method shown below.

T1: diethoxy(3-glycidyloxypropyl)methylsilane (made by Tokyo Chemical Industry).

T2: Tetraethoxysilane (manufactured by Tokyo Chemical Industry).

T3: N,N,N',N'-TETRAGLYCIDYL-4,4'-DIAMINODIPHENYLMETHANE (manufactured by Aldrich).

T4: Butanetetracarboxylic acid tetra(3,4-epoxycyclohexylmethyl) modification epsilon -caprolactone.

T5: Triglycidyl isocyanurate (made by Tokyo Chemical Industry).

T6: A known compound.

T7: 3,4-epoxycyclohexyl3,4-epoxycyclohexanecarboxylate (manufactured by Aldrich).

T8: A known compound.

T9: Dipentaerythritol hexaacrylate (Daisel Cytec Co., Ltd.).

T10: 2,4,6-tris[bis(methoxymethyl)amino]-1,3,5-triazine (manufactured by Tokyo Chemical Industry).

T11: 2,2'-bis(4-hydroxy-3,5-dihydroxymethylphenyl) propane (made by Asahi Organic Materials Co., Ltd.).

T12: Tris(4-(vinyloxy)butyl) trimellitate (manufactured by Aldrich).

T13: 1,3-bis(4,5-dihydro-2-oxazolyl)benzene (made by Tokyo Chemical Industry).

T14: VestanatB (manufactured by evonik).

[Formula 38]

In addition, the abbreviation of the reagent used in this Example is shown below.

(organic solvent)

THF: tetrahydrofuran.

NMP: N-methyl-2-pyrrolidone.

BC: Butyl cellosolve.

(Polymerization Initiator)

AIBN: 2,2'-azobisisobutyronitrile.

<Synthesis Example 1>

After dissolving MA1 (9.97 g, 30.0 mmol) in THF (92.0 g) and deaeration with a diaphragm pump, AIBN (0.246 g, 1.5 mmol) was added to deaeration again. Then, it was made to react at 50 degreeC for 30 hours, and the polymer solution of methacrylate was obtained. This polymer solution was added dropwise to diethyl ether (1000 ml), and the precipitate obtained by filtering the resulting precipitate was washed with diethyl ether and dried under reduced pressure in an oven at 40°C to obtain a methacrylate polymer powder (A1).

NMP (29.3g) was added to the obtained methacrylate polymer powder (A1) (6.0g), and it stirred at room temperature for 5 hours, and was made to melt|dissolve. Methacryl polymer solution M1 was obtained by adding and stirring NMP (24.7g) and BC (40.0g) to this solution.

<Synthesis Example 2>

MA1 (4.99 g, 15.0 mmol) and MA2 (4.60 g, 15.0 mmol) were dissolved in THF (88.5 g), deaerated with a diaphragm pump, and then degassed again by adding AIBN (0.246 g, 1.5 mmol). carried out. Then, it was made to react at 50 degreeC for 30 hours, and the polymer solution of methacrylate was obtained. This polymer solution was added dropwise to diethyl ether (1000 ml), and the obtained precipitate was filtered. This deposit was wash|cleaned with diethyl ether, it was made to dry under reduced pressure in 40 degreeC oven, and the methacrylate polymer powder (A2) was obtained.

NMP (54.0g) was added to the obtained methacrylate polymer powder (A2) (6.0g), and it stirred at room temperature for 5 hours, and was made to melt|dissolve. To this solution, BC (40.0 g) was added and stirred to obtain a methacrylic polymer solution M2.

<Example 1>

0.015 g of T1 was added to 5.0 g of methacryl polymer solution M1 obtained by the synthesis example 1, it stirred at room temperature for 3 hours, and liquid crystal aligning agent A1 was obtained.

The liquid crystal cell was produced in the procedure as shown below using this liquid crystal aligning agent A1. The substrate was a glass substrate having a size of 30 mm × 40 mm, a thickness of 0.7 mm, and a comb-tooth-shaped pixel electrode formed by patterning an ITO film was used.

The pixel electrode had the comb-tooth-shaped shape comprised by arranging a plurality of "<"-shaped electrode elements in which the central part was bent. The width in the transverse direction of each electrode element was 10 mu m, and the distance between the electrode elements was 20 mu m. Since the pixel electrode forming each pixel is constituted by arranging a plurality of "<"-shaped electrode elements in which the central part is bent, the shape of each pixel is not a rectangular shape, but a thick, curved, central part similarly to the electrode element. It has a shape resembling the letter 'K'.

Each pixel was divided|segmented up and down with the bent part in the center as a boundary, and had the 1st area|region above the curved part, and the 2nd area|region below. Comparing the 1st area|region and 2nd area|region of each pixel, the formation direction of the electrode element of the pixel electrode which comprises them was found to be different. That is, based on the alignment treatment direction of the liquid crystal alignment film to be described later, in the first region of the pixel, the electrode element of the pixel electrode is formed to form an angle of +15° (clockwise), and in the second region of the pixel, the pixel electrode The electrode elements were formed to form an angle of -15° (clockwise). That is, in the first region and the second region of each pixel, the directions of the rotational operation (in-plane switching) in the substrate plane of the liquid crystal caused by the voltage application between the pixel electrode and the counter electrode are opposite to each other. was composed

<<Preparation of liquid crystal cell>>

Liquid crystal aligning agent A1 obtained in Example 1 was spin-coated to the board|substrate with the prepared said electrode. Then, it dried for 90 second with a 70 degreeC hotplate, and formed the liquid crystal aligning film with a film thickness of 100 nm. Then, after irradiating 20 mJ/cm<2> of 313 nm ultraviolet-ray to the coating film surface through a polarizing plate, it heated for 10 minutes with a 150 degreeC hotplate, and obtained the board|substrate with a liquid crystal aligning film. Moreover, it orientation-processed by forming a coating film similarly also to the glass substrate which has a 4 micrometers height columnar spacer in which the electrode is not formed as a counter board|substrate. The sealing compound (XN-1500T by Kyoritsu Chemical) was printed on the liquid crystal aligning film of one board|substrate. Then, the liquid crystal aligning film surface faced and the other board|substrate was adhere|attached so that an orientation direction might be set to 0 degree, and then, the sealing compound was thermosetted and the empty cell was produced. Liquid crystal MLC-2041 (made by Merck Corporation) was inject|poured into this empty cell by the reduced pressure injection method, the injection port was sealed, and the liquid crystal cell provided with the structure of IPS(In-Planes Switching) mode liquid crystal display element was obtained.

<Voltage retention rate (VHR) evaluation>

Using the liquid crystal cell produced above, the alternating voltage of 16Vpp was applied by the frequency 30Hz in a 70 degreeC constant temperature environment for 168 hours. Then, it was set as the state made short between the pixel electrode of a liquid crystal cell, and a counter electrode, and it was left to stand at room temperature as it is for 1 hour. The obtained cell was applied with a voltage of 5 V for 60 µs under a temperature of 70°C, the voltage after 16.67 ms was measured, and how much the voltage was maintained was calculated as the voltage retention (VHR). In addition, voltage retention measuring apparatus VHR-1 by the Toyo Technica company was used for the measurement of voltage retention.

<Adhesiveness evaluation>

<<Sample Production>>

The sample of adhesive evaluation was produced as follows. The liquid crystal aligning agent was spin-coated to a 30 mm x 40 mm ITO board|substrate, and it was made to dry for 90 second with a 70 degreeC hotplate. Then, after 20 mJ/cm<2> of 313 nm ultraviolet-rays were irradiated to the coating surface through a deflection plate, it heated for 10 minutes with a 150 degreeC hotplate, and obtained the board|substrate with a liquid crystal aligning film of 100 nm in film thickness.

After apply|coating the 6 micrometers bead spacer to this board|substrate, the sealing compound (XN-1500T by Kyoritsu Chemical) was dripped on the liquid crystal aligning film of one board|substrate. Next, after bonding and fixing the other board|substrate with a clip so that the width|variety of a sealing compound might be set to 1 cm, the other board|substrate was thermosetted at 150 degreeC for 1 hour, and the sample for adhesive evaluation was produced.

<<Measurement of Adhesion>>

After that, the sample substrate was fixed with a tabletop precision universal testing machine AGS-X 500N manufactured by Shimadzu Corporation, and the end portions of the upper and lower substrates were fixed, and then pressed from the upper portion of the center of the substrate, and the pressure at the time of peeling (N) was measured. The result of voltage retention (VHR) and the adhesive measurement result are shown in Table 1 with the composition of the liquid crystal aligning agent of Example 1.

<Examples 2 to 18>

Liquid crystal aligning agents A2 to A18 of Examples 2-18 were obtained by the method similar to Example 1 except having used the composition shown in Table 1, and the liquid crystal cell and the sample for adhesive evaluation were prepared using this. Moreover, voltage retention (VHR) and adhesiveness were measured by the method similar to Example 1. The results are also shown in Table 1.

<Controls 1 and 2>

The liquid crystal aligning agents of Controls 1 and 2 did not have an additive, but used methacryl polymer solutions M1 and M2, respectively. A liquid crystal cell and the sample for adhesive evaluation were prepared by the method similar to Example 1 except having used the methacryl polymer solutions M1 and M2 as a liquid crystal aligning agent. Moreover, voltage retention (VHR) and adhesiveness were measured by the method similar to Example 1. The results are also shown in Table 1.

Table 1 shows that in Examples 1 to 18, the voltage retention (VHR) is improved by using the additive as compared with Controls 1 and 2 not using the additive.

Moreover, in Examples 1-5 and Example 7, it turns out that adhesiveness is high compared with Control 1 and 2 which does not use an additive by using an additive.

<Afterimage evaluation>

The liquid crystal cell for IPS mode prepared in Example 1 is installed between two polarizing plates arranged so that the polarization axes are orthogonal to each other, the backlight is turned on in a state where no voltage is applied, and the angle of arrangement of the liquid crystal cell so that the luminance of transmitted light is the smallest. was adjusted And the rotation angle at the time of rotating a liquid crystal cell from the angle at which the 2nd area|region of a pixel becomes the darkest to the angle at which the 1st area|region becomes the darkest was computed as an initial stage orientation azimuth. Next, the alternating voltage of 16V _PP was applied at the frequency of 30 Hz in 60 degreeC oven for 168 hours. Then, it was set as the state made short between the pixel electrode of a liquid crystal cell, and a counter electrode, and it was left to stand at room temperature as it is for 1 hour. After leaving it to stand, the orientation azimuth was measured similarly, and the difference of orientation azimuth before and behind an alternating current drive was computed as angle (DELTA)(deg.). Measurements were also made in the same manner in other Examples. As a result, in all Examples, the angle Δ was 0.1 or less. After irradiating an ultraviolet-ray to the side chain type polymer film which expresses liquid crystallinity, by heating in the liquid crystal expression temperature range, it is because liquid crystal orientation ability is provided with high efficiency in the whole polymer by self-organization, or the orientation orientation even after long-term AC drive. No deviation was observed.

Figure 1
1: side chain type polymer membrane
2, 2a: side chain
Figure 2
3: side chain type polymer membrane
4, 4a: side chain
Fig. 3
5: side chain polymer membrane
6, 6a: side chain
Fig. 4
7: side chain polymer membrane
8, 8a: side chain

Claims (16)

(A) a photosensitive side chain polymer which expresses liquid crystallinity in a predetermined temperature range;
(B) a cross-linkable compound having at least one substituent selected from a hydroxyl group, a hydroxyalkyl group, an alkoxy group, an oxirane group, an epoxy group, a cyclocarbonate group, and a trialkoxysilyl group in one molecule, and
(C) organic solvent
As a polymer composition containing,
The said (A) component is following formula (7) - (9)
(Wherein, A, B, D are each independently a single bond, -O-, -CH ₂ -, -COO-, -OCO-, -CONH-, -NH-CO-, -CH=CH-CO- represents O- or -O-CO-CH=CH-;
Y ₁ represents a ring selected from a monovalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring, and an alicyclic hydrocarbon having 5 to 8 carbon atoms, or the same or different 2 to 6 rings selected from their substituents is a group formed by bonding via a bonding group B, and the hydrogen atoms bonded thereto are each independently -COOR ₀ (wherein R ₀ represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms), -NO ₂ , - CN, -CH=C(CN) ₂ , -CH=CH-CN, a halogen group, a C1-C5 alkyl group, or a C1-C5 alkyloxy group may be substituted;
X is a single bond in formulas (7) and (8), -COO-, -OCO-, -N=N-, -CH=CH-, -C≡C-, -CH=CH-CO-O-, or -O-CO-CH=CH-, represents a single bond in formula (9), and when the number of X becomes 2, X may be the same or different;
l represents the integer of 1-12;
m represents the integer of 0-2;
n represents an integer of 0 to 12 (provided that when n = 0, B is a single bond);
Y ₂ is a group selected from the group consisting of a divalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring, an alicyclic hydrocarbon having 5 to 8 carbon atoms, and combinations thereof, and a hydrogen atom bonded thereto is each independently -NO ₂ , -CN, -CH=C(CN) ₂ , -CH=CH-CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or an alkyloxy group having 1 to 5 carbon atoms;
R represents a hydroxy group or an alkoxy group having 1 to 6 carbon atoms)
Any one type of photosensitive side chain selected from the group consisting of,
(A) The component has the following formulas (27) to (31) (wherein A and B have the same definitions as above;
l represents the integer of 1-12, m3 represents the integer of 1-3, has any 1 type of liquid crystalline side chain chosen from the group which consists of),
It has a main chain composed of at least one selected from the group consisting of acrylate, (meth)acrylate, itaconate, fumarate, maleate, α-methylene-γ-butyrolactone, vinyl and siloxane,
The (B) component is 0.1-50 parts by mass with respect to 100 parts by mass of the polymer component,
The crosslinkable compound is diethoxy(3-glycidyloxypropyl)methylsilane, tetraethoxysilane, triglycidyl isocyanurate, tetraglycidylaminodiphenylene, tetraglycidyl-m-xyl Lendiamine, tetraglycidyl-1,3-bis(aminoethyl)cyclohexane, tetraglycidyl metaxylenediamine, N,N,N',N'-tetraglycidyl-4,4'-dia minodiphenylmethane, a compound represented by the following formula T4, a compound represented by the following formula T6, or a compound represented by the following formula T8;
(C) the organic solvent is N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, N-methylcaprolactam, Dimethyl sulfoxide, tetramethyl urea, hexamethyl sulfoxide, γ-butyrolactone, methoxymethylpentanol, dipentene, ethyl amyl ketone, methyl nonyl ketone, methyl isoamyl ketone, methyl cellosolve, ethyl cello Solve, methyl cellosolve acetate, ethyl cellosolve acetate, butyl carbitol, ethyl carbitol, ethylene glycol, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, propylene glycol, propylene glycol monomethyl ether, propylene glycol- tert-butyl ether, dipropylene glycol monomethyl ether, diethylene glycol, diethylene glycol dimethyl ether, dipropylene glycol monoacetate monomethyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monoacetate Monoethyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monoacetate monopropyl ether, 3-methyl-3-methoxybutyl acetate, tripropylene glycol methyl ether, 3-methyl-3-methoxybutanol, ethyl isobutyl Ether, amyl acetate, butyl butyrate, butyl ether, diisobutyl ketone, methylcyclohexene, dihexyl ether, n-octane, cyclohexanone, ethylene carbonate, propylene carbonate, methyl lactate, ethyl lactate, n-butyl acetate, Acetate propylene glycol monoethyl ether, methyl pyruvate, ethyl pyruvate, 3-methoxy methyl propionate, 3-ethoxy methyl ethyl propionate, 3-methoxy ethyl propionate, 3-ethoxy propionic acid, 3-methoxypropionic acid, 3-methyl Propyl oxypropionate, 3-methoxybutyl propionate, diglyme, 4-hydroxy-4-methyl-2-pentanone, 3-methoxy-N,N-dimethylpropanamide, 3-ethoxy-N,N- The polymer composition, which is at least one selected from the group consisting of dimethylpropanamide and 3-butoxy-N,N-dimethylpropanamide.

The method of claim 1,
(A) A composition having a photosensitive side chain in which the component causes photocrosslinking, photoisomerization, or photofleece transition. The method of claim 1,
The said polymer composition is a composition for liquid crystal aligning film manufacture for transverse electric field drive type liquid crystal display elements, The composition. [I] The process of apply|coating the composition of Claim 1 on the board|substrate which has an electrically conductive film for lateral electric field drive, and forming a coating film;
[II] The process of irradiating the polarized ultraviolet-ray to the coating film obtained in [I]; And
[III] Process of heating the coating film obtained in [II];
The manufacturing method of the board|substrate which has the said liquid crystal aligning film which obtains the liquid crystal aligning film for transverse electric field drive type liquid crystal display elements to which orientation control ability was provided by having. The board|substrate which has a liquid crystal aligning film for lateral electric field drive type liquid crystal display elements manufactured by the method of Claim 4. A transverse electric field drive type liquid crystal display element which has the board|substrate of Claim 5. [I] The process of applying the composition of Claim 1 on the 1st board|substrate which has the electrically conductive film for lateral electric field drive, and forming a coating film;
[II] The process of irradiating the polarized ultraviolet-ray to the coating film obtained in [I]; And
[III] Process of heating the coating film obtained in [II];
The process of preparing the 1st board|substrate which has the said liquid crystal aligning film which obtains the liquid crystal aligning film for transverse electric field drive type liquid crystal display elements to which orientation control ability was provided by having;
[I'] The process of apply|coating the composition of Claim 1 on a 2nd board|substrate, and forming a coating film;
[II'] The process of irradiating the polarized ultraviolet-ray to the coating film obtained by [I']; And
[III'] The process of heating the coating film obtained by [II'];
The process of obtaining the 2nd board|substrate which has the said liquid crystal aligning film which obtains the liquid crystal aligning film to which orientation control ability was provided by having; And
[IV] The process of opposingly arrange|positioning a said 1st and 2nd board|substrate and obtaining a liquid crystal display element so that the liquid crystal aligning film of a said 1st and 2nd board|substrate may oppose through a liquid crystal;
The manufacturing method of the liquid crystal display element which obtains a transverse electric field drive type liquid crystal display element by having. A transverse electric field driving type liquid crystal display device manufactured by the method according to claim 7. delete delete delete delete delete delete delete delete

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