KR20220048487A - Liquid crystal aligning agent, liquid crystal alignment film and liquid crystal display element - Google Patents

Abstract

ADVANTAGE OF THE INVENTION According to this invention, the novel polymer composition which provides the liquid crystal aligning film for transverse electric field drive type liquid crystal display elements which is provided with orientation control ability with high efficiency and is excellent in burn-in characteristics, and a transverse electric field drive type using the same A liquid crystal aligning film for a liquid crystal display element is provided.
The present invention relates to (A) a side chain (a1) having a photoreactive moiety represented by the following formula (a), a side chain (a2) having a photoreactive moiety different from the photoreactive moiety represented by the following formula (a), and Side chain type polymer|macromolecule which has a side chain (a3) which expresses liquid crystallinity; and (B) an organic solvent.

Description

A liquid crystal aligning agent, a liquid crystal aligning film, and a liquid crystal display element {LIQUID CRYSTAL ALIGNING AGENT, LIQUID CRYSTAL ALIGNMENT FILM AND LIQUID CRYSTAL DISPLAY ELEMENT}

The present invention relates to a liquid crystal aligning agent, a liquid crystal aligning film, and a liquid crystal display element using the same, and a polymer film suitable for manufacturing an optical element in which molecular orientation such as a retardation film or a polarization diffraction element is controlled.

BACKGROUND ART A liquid crystal display element is known as a light-weight, thin, and low-power display device, and in recent years it is used for a large-scale television use, and has 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, a 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 is playing 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 (henceforth orientation control ability) is provided by orientation-processing with respect to the organic film which comprises a liquid crystal aligning film.

Conventionally, the rubbing method is known as an orientation processing method of the liquid crystal aligning film for providing orientation control ability. In the rubbing method, the surface of an organic film such as polyvinyl alcohol or polyamide or polyimide on a substrate is rubbed in a certain direction with a cloth such as cotton, nylon, or polyester in a certain direction (rubbing), in the 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, as for the rubbing method of rubbing the surface of the liquid crystal aligning film which consists of polyimide etc., generation|occurrence|production of dust generation and static electricity may become a problem. In addition, due to the recent high-definition liquid crystal display devices, and irregularities caused by the electrodes on the corresponding substrates and the switching active devices 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 the main alignment method, a "photolysis type" that generates anisotropic decomposition in the molecular structure by irradiation with polarized ultraviolet light or polyvinyl cinnamate is used and polarized ultraviolet light is irradiated to two sides parallel to polarized light. When using a "dimerization type" that generates a dimerization reaction (crosslinking reaction) in the double bond portion of the chain (see, for example, Patent Document 1), and a side chain type polymer having azobenzene in the side chain, polarized ultraviolet light The "isomerization type" (for example, refer nonpatent literature 2) which produces an isomerization reaction in the azobenzene part of a side chain parallel to polarization|polarized-light and orientates a liquid crystal in the direction orthogonal to a polarization direction is known.

On the other hand, the new photo-alignment method (henceforth an orientation amplification method) using the photosensitive side chain type polymer|macromolecule which can express liquid crystallinity is examined in recent years. This is to the film|membrane which has a photosensitive side chain type polymer|macromolecule which can express liquid crystallinity, orientation-processed by polarized light irradiation, and after that, through the process of heating the side chain type polymer film|membrane, orientation control ability was provided to get a coating. At this time, the slight anisotropy expressed by polarized light irradiation becomes a driving force, and liquid crystalline side chain type polymer|macromolecule itself reorient|orients efficiently 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 (for example, refer patent document 2).

In addition, the polymer film obtained by this orientation amplification method can be used as various optical elements, such as retardation film, in addition to the use of a liquid crystal aligning film, since birefringence is expressed by molecular orientation.

Japanese Patent No. 3893659 WO2014/054785

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

The irradiation amount of the polarized ultraviolet light optimal for highly efficient anisotropy introduction to the liquid crystal aligning film used for the orientation amplification method corresponds to the irradiation amount of the polarized ultraviolet light which optimizes the amount with which the photosensitive group photoreacts in the coating film. As a result of irradiating the ultraviolet-ray which polarized with respect to the liquid crystal aligning film used for the orientation amplification method, when there are few photosensitive groups of the side chain which photoreacts, it will not become sufficient photoreaction amount. In that case, even if it heats after that, sufficient self-organization does not advance. On the other hand, when the photosensitive group of the photoreactive side chain becomes excess, the film|membrane obtained becomes rigid, and it may become hindrance of advancing of the self-assembly by subsequent heating.

Currently, among the liquid crystal aligning films used for the orientation amplification method, the area of the irradiation amount of the above-mentioned optimal polarization|polarized-light ultraviolet-ray is narrow, perhaps because the sensitivity of the photoreactive group in the polymer used is high. As a result, the fall of the manufacturing efficiency of a liquid crystal display element poses a problem.

In addition, when the firing temperature of the liquid crystal aligning film is low, the reliability of the liquid crystal display element may decrease due to the influence of residual solvents, etc., but the liquid crystal aligning agent obtained by the orientation amplification method has a temperature higher than the liquid crystal expression temperature of the polymer liquid crystal due to its properties. Since firing cannot be carried out in , the firing temperature is generally low, and residual solvents and the like are one factor that lowers reliability.

Then, an object of this invention is to provide the liquid crystal aligning film with a wide process margin in which orientation control ability is provided with high efficiency, and can adjust to an optimal polarization|polarized-light ultraviolet irradiation amount and an optimal baking temperature.

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) side chain (a1) having a photoreactive moiety represented by the following formula (a), a side chain (a2) having a photoreactive moiety different from the photoreactive moiety represented by the following formula (a), and liquid crystal Side chain type polymer|macromolecule which has a side chain (a3) which expresses sex; and

(B) organic solvent

A polymer composition containing

[Formula 1]

In <2> said <1>, it is preferable that the said side chain (a2) is a photosensitive side chain which raise|generates photocrosslinking, photoisomerization, or an optical Fries dislocation.

In <3> said <1> or <2>, the said side chain (a2) is any 1 type of photosensitive side chain chosen from the group which consists of following formula (1)-(6), Comprising: said Formula (a It is preferable that it is a side chain which has a photoreactive site|part different from the photoreactive site|part represented by ).

[Formula 2]

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-;

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 a C1-C12 alkylene group, and the hydrogen atom couple|bonded with them may be substituted by the 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 2 to 6 identical or different selected from their substituents A ring is a group formed by bonding through 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 furan ring, a pyrrole ring, an alicyclic hydrocarbon having 5 to 8 carbon atoms, and combinations thereof, and the hydrogen atoms bonded thereto are each independently - NO2, -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;

R represents a hydroxyl group or 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= When CH- is represented and the number of X becomes 2, X may be 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, You may substituted with a halogen group, a C1-C5 alkyl group, or a C1-C5 alkyloxy group;

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 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; 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, and the number of P is 2 or more When it becomes, P may be 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.

<4> In any one of said <1>-<3>, it is that the said side chain (a3) is any 1 type of liquid crystalline side chain chosen from the group which consists of following formula (21)-(31) desirable.

wherein A and B 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, nitrogen-containing A heterocyclic ring, a C5-C8 alicyclic hydrocarbon, a C1-C12 alkyl group, or a C1-C12 alkoxy group is represented;

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

l represents the integer of 1-12, m represents the integer of 0-2, provided that in Formulas (23)-(24), the sum of all m is 2 or more, Formulas (25)-(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 3]

<5> [I] A step of forming a coating film by applying the composition according to any one of <1> to <4> above on a substrate having a conductive film for lateral electric field drive;

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

[III] A step 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 lateral electric field drive type liquid crystal display elements to which orientation control ability was provided by having.

<6> A substrate having a liquid crystal aligning film for a transverse electric field driving type liquid crystal display element manufactured by the method of <5>.

<7> A transverse electric field driving type liquid crystal display device having the substrate according to <6>.

<8> step of preparing the substrate (first substrate) according to <6>;

[I'] A step of applying the polymer composition in any one of <1> to <17> above on a second substrate to form a coating film;

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

[III'] A step of heating the coating film obtained in [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.

<9> Transverse electric field driving type liquid crystal display device manufactured according to <8>.

According to this invention, when the polymer which has a specific structural unit can be obtained and the obtained polymer sets it as a liquid crystal aligning film, it shows favorable orientation in a UV irradiation amount more extensive than the conventional polymer. Thereby, in order to implement|achieve the various characteristics requested|required of a liquid crystal display element, when performing a photo-alignment process, it can carry out with the polarization|polarized-light UV irradiation amount various than conventionally, and productivity improves. As a result, 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 burn-in characteristics, and a transverse electric field driving type liquid crystal display element having the substrate, with good yield can do.

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 of the present invention has a photosensitive side chain polymer (hereinafter also simply referred to as a side chain polymer) capable of expressing liquid crystallinity, and the coating film obtained using the polymer composition is capable of expressing liquid crystallinity. It is a film having a photosensitive side chain polymer. It orientation-processes by polarized light irradiation, without giving a rubbing process to this coating film. And it becomes the 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 reorient|orients efficiently 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.

Moreover, in the polymer composition in this invention, the side chain type polymer|macromolecule which is (A) component contains the side chain represented by the said Formula (a). Thereby, the liquid crystal aligning film obtained from the polymer composition of this invention shows favorable orientation in a more extensive UV irradiation amount as UV irradiation amount at the time of manufacture. As for this phenomenon, since the photoreactive site|part represented by said Formula (a) is a long conjugated system, it has a fluorescence characteristic, and thereby absorbs an ultraviolet-ray. Therefore, it was thought that the irradiation margin was expanded by using the polymer which copolymerized the monomer which has the photoreactive site|part represented by the said Formula (a). They also include the inventors' views regarding the mechanism of the present invention, but do not limit the present invention.

Moreover, in the polymer composition in this invention, in addition to the side chain type polymer|macromolecule which is (A) component, and the organic solvent which is (B) component, as (C)component, a tetracarboxylic acid derivative and a diamine compound are polymerized and manufactured Polyamic acid to be used, or polyimide produced by imidizing polyamic acid, polyurea produced by polymerization reaction of a diisocyanate compound and a diamine compound, a diisocyanate compound and a tetracarboxylic acid derivative, and a diamine compound The polyurea polyamic acid to be used and polyurea polyimide produced by imidizing the polyurea polyamic acid may be contained.

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

<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 in the production method of the present invention comprises:

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

The side chain (a1) which has a photoreactive site|part represented by following formula (a);

A side chain (a2) having a photoreactive moiety different from the photoreactive moiety represented by the following formula (a), and

The side chain (a3) which expresses liquid crystallinity

A side chain polymer having; and

(B) organic solvent

It is characterized in that it contains

[Formula 4]

<<(A) side chain polymer >>

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

A side chain (a1) having a photoreactive site represented by the formula (a);

a side chain (a2) having a photoreactive site different from the photoreactive site represented by the formula (a);

The side chain (a3) which expresses liquid crystallinity

has

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

(A) Since side chain type polymer|macromolecule of component shows liquid crystallinity in the temperature range of 100 degreeC - 300 degreeC, it is preferable to have a side chain (a3) which expresses liquid crystallinity.

<<<Side chain (a2): Side chain >> which has a photoreactive site|part differing from the photoreactive site|part represented by Formula (a)>>>

(A) Side chain type polymer|macromolecule of a component has a side chain (a2) which has a photoreactive site|part different from the photoreactive site|part represented by Formula (a). Here, "having a photoreactive moiety different from the photoreactive moiety represented by the formula (a)” means having a photoreactive moiety but not having the photoreactive moiety represented by the formula (a). That is, while a side chain (a2) has the site|part which responds to light and raise|generates a crosslinking reaction, an isomerization reaction, or an optical Fries rearrangement, the photoreactive site|part represented by Formula (a) means the side chain which does not have.

The side chain which has photosensitivity is couple|bonded with the main chain, and the side chain type polymer|macromolecule of (A) component can generate|occur|produce a crosslinking reaction, an isomerization reaction, or an optical Fries dislocation in response to light. 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 photosensitive side chain type polymer|macromolecule 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 mesogenic component such as a biphenyl group, a terphenyl group, a phenylcyclohexyl group, a phenylbenzoate group, and an azobenzene group; , has a structure having a photosensitive group that reacts with light and undergoes a crosslinking reaction or an isomerization reaction, bonded to the tip, and a main chain and a side chain bonded thereto, the side chain also serves as a mesogenic component, and also an optical Fris rearrangement reaction It can be made into a structure having a phenyl benzoate group.

More specific examples of the photosensitive side chain polymer structure capable of expressing liquid crystallinity include (meth)acrylate, itaconate, fumarate, maleate, α-methylene-γ-butyrolactone, styrene, vinyl, It is a structure having a main chain composed of at least one selected from the group consisting of radically polymerizable groups such as maleimide and norbornene and siloxane, and a side chain composed of at least one of the following formulas (1) to (6) desirable.

[Formula 5]

In the formulas (1) to (6), A, B, and D are each independently a single bond, -O-, -CH ₂ -, -COO-, -OCO-, -CONH-, -NH-CO- , -CH=CH-CO-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 a C1-C12 alkylene group, and the hydrogen atom couple|bonded with them may be substituted by the 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 2 to 6 identical or different selected from their substituents A ring is a group formed by bonding through 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 furan ring, a pyrrole ring, an alicyclic hydrocarbon having 5 to 8 carbon atoms, and combinations thereof, and the hydrogen atoms bonded thereto are each independently - NO2, -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;

R represents a hydroxyl group or 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= When CH- is represented and the number of X becomes 2, X may be 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, You may substituted with a halogen group, a C1-C5 alkyl group, or a C1-C5 alkyloxy group;

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 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; 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, and the number of P is 2 or more When it becomes, P may be 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.

According to a preferable aspect of this invention, a side chain (a2) is any 1 type of photosensitive side chain chosen from the group which consists of said Formula (1)-(6), The photoreactive site|part represented by the said Formula (a), is a side chain with different photoreactive sites.

It is preferable that a side chain (a2) is 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 6]

It is preferable that a side chain (a2) 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 7]

It is preferable that a side chain (a2) 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 8]

It is preferable that a side chain (a2) 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 9]

Moreover, it is preferable that a side chain (a2) 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 10]

It is preferable that a side chain (a2) 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 11]

<<<Side chain (a1): Side chain>>> which has a photoreactive site|part represented by Formula (a)

Moreover, side chain type polymer|macromolecule of (A) component contains the side chain (a1) which has a photoreactive site|part represented by following formula (a).

[Formula 12]

As a side chain (a1), the side chain represented, for example by a following formula (a1-1) is preferable.

[Formula 13]

In formula (a1-1), L is a C1-C16 linear or branched alkylene.

In formula (a1-1), X represents a single bond, -O-, -C(=O)-O-, or -O-C(=O)-.

<<<side chain (a3): side chain which expresses liquid crystallinity >>>

Furthermore, the side chain type polymer|macromolecule of (A) component contains the side chain (a3) which expresses liquid crystallinity. Here, the side chain (a3) is a side chain which expresses liquid crystallinity, and is a side chain which itself can express mesogenicity, or a side chain which can express mesogenicity by dimerizing by hydrogen bond etc. say

That is, as a side chain (a3) which expresses liquid crystallinity in side chain type polymer|macromolecule of (A) component, any 1 type chosen from the group which consists of following formula (21)-(31), for example It is preferable that it is a liquid crystalline side chain.

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, nitrogen-containing A heterocyclic ring, a C5-C8 alicyclic hydrocarbon, a C1-C12 alkyl group, or a C1-C12 alkoxy group is represented;

l represents the integer of 1-12, m represents the integer of 0-2, provided that in Formulas (23)-(24), the sum of all m is 2 or more, Formulas (25)-(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 14]

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

The photosensitive side chain type polymer|macromolecule which can express said liquid crystallinity is the monomer which has a structural unit represented by Formula (a), The photoreactive side which has a photoreactive site|part different from the photoreactive site|part represented by said Formula (a) It can obtain by superposing|polymerizing a chain monomer (M1) and a liquid crystalline side chain monomer (M2).

[Monomer having a structural unit represented by formula (a)]

As a monomer which has a structural unit represented by Formula (a), the compound represented by a following formula (am1-1) is mentioned.

[Formula 15]

In formula (am1-1), L is a C1-C16 linear or branched alkylene.

In formula (am1-1), X represents a single bond, -O-, -C(=O)-O-, or -O-C(=O)-.

In formula (am1-1), PL is a polymerizable group, and represents a polymerizable group selected from the group consisting of the following formulas PL-1 to PL-5. In formulas PL-1 to PL-5, R ¹ , R ² , and R ³ are a hydrogen atom, a linear or branched alkyl group having 1 to 10 carbon atoms, or a linear or branched chain or branched chain having 1 to 10 carbon atoms substituted with halogen. represents the chain alkyl group (* represents the bonding position with L).

[Formula 16]

Among these monomers, any of them are commercially available, and any of them can be prepared from known substances by known production methods.

[Photoreactive side chain monomer (M1)]

A photoreactive side chain monomer means the monomer which can form the polymer|macromolecule which has the said photosensitive side chain (a2) in the side chain site|part of a polymer, when polymer|macromolecule is formed.

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

[Formula 17]

More specific examples of the photoreactive side chain monomer include radicals such as (meth)acrylate, itaconate, fumarate, maleate, α-methylene-γ-butyrolactone, styrene, vinyl, maleimide, norbornene The photosensitive side chain which consists of a polymeric group comprised by at least 1 type selected from the group which consists of a polymeric group and siloxane, and at least 1 type of said Formula (1)-(6) Preferably, for example, said Formula (7 The photosensitive side chain which consists of at least 1 type of )-(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), said It is preferable that it is a structure which has the photosensitive side chain represented by the photosensitive side chain represented by Formula (16) or (17), the photosensitive side chain represented by said Formula (18) or (19), and said Formula (20).

More specific examples of the monomer (M1) include hydrocarbon, (meth)acrylate, itaconate, fumarate, maleate, α-methylene-γ-butyrolactone, styrene, vinyl, maleimide, norbornene. A structure that expresses photoreactivity and liquid crystallinity composed of a polymerizable group composed of at least one selected from the group consisting of a radical polymerizable group and siloxane, and at least one of the formulas (1) to (6), preferably, examples For example, a structure which expresses the photoreactivity and liquid crystal property which consists of at least 1 type of said Formula (7) - (10), and the photoreactivity and liquid crystal property which consists of at least 1 type of said Formula (11) - (13) are expressed a structure that expresses the photoreactivity and liquid crystallinity represented by the formula (14) or (15), a structure that expresses the photoreactivity and liquid crystallinity represented by the formula (16) or (17), the formula (18) Or it is preferable that it is a structure which has a structure which expresses the photoreactivity and liquid crystalline property represented by (19), and the structure which expresses the photoreactivity and liquid crystalline property represented by said Formula (20).

Monomer (M1) is a polymerizable group in the following formulas MA1, MA3, MA4, MA5, MA14, MA16 to MA23, MA25, MA28 to MA30, MA32, MA34, MA36, MA38 to MA42, MA44 and MA46, and their compounds. The polymerizable group of the compound having methacrylate is selected from the group consisting of acrylate, itaconate, fumarate, maleate, α-methylene-γ-butyrolactone, styrene, vinyl, maleimide, norbornene and siloxane It is preferable that it is at least 1 sort(s) chosen from the compound substituted by the polymeric group used. In particular, it is preferable that a monomer (M1) has a (meth)acrylate as a polymeric group, Preferably, it is preferable that the terminal of a side chain is COOH, Preferably, for example.

In addition, MA1-MA46 can be synthesize|combined as follows.

MA1 can be synthesized by the synthesis method described in Patent Literature (WO2011-084546).

MA2 can be synthesized by the synthesis method described in Patent Document (Japanese Patent Application Laid-Open No. 9-118717).

MA3 can be synthesized by the synthesis method described in the non-patent literature (Macromolecules 2002, 35, 706-713).

MA4 can be synthesized by the synthesis method described in Patent Literature (WO2014/054785).

MA5 can be synthesized by the synthesis method described in patent document (Unexamined-Japanese-Patent No. 2010-18807).

MA6-MA9 can be synthesize|combined by the synthesis|combining method described in patent document (WO2014/054785).

As MA10, commercially available M6BC (manufactured by Midori Chemical Co., Ltd.) can be used.

MA11-13 can be synthesize|combined by the synthesis|combining method described in patent document (WO2014/054785).

For MA14 to 18, commercially available M4CA, M4BA, M2CA, M3CA, and M5CA (all of which are manufactured by Midori Chemical Co., Ltd.) can be used.

MA19-23 can be synthesized by the synthesis method described in patent document (WO2014/054785).

MA24 can be synthesized by the synthesis method described in a non-patent literature (Polymer Journal, Vol.29, No.4, pp303-308 (1997)).

MA25 can be synthesized by the synthesis method described in Patent Document (WO2014/054785).

MA26 and MA27 are synthetic methods described in non-patent literature (Macromolecules (2012), 45 (21), 8547-8554) and non-patent literature (Liquid Crystals (1995), 19 (4), 433-40), respectively. synthesis can be carried out.

MA28-33 can be synthesize|combined by the synthesis|combining method described in patent document (WO2014/054785).

MA34-39 can be synthesized by the synthesis method described in patent document (WO2014/054785).

MA40 and 41 can be synthesize|combined by the synthesis method described in patent document (Unexamined-Japanese-Patent No. 2009-511431).

MA42 can be synthesized by the synthesis method described in patent document (WO2014/054785).

MA43 can be synthesized by the synthesis method described in patent document (WO2012-115129).

MA44 can be synthesized by the synthesis method described in Patent Document (WO2013-133078).

MA45 can be synthesized by the synthesis method described in Patent Document (WO2008-072652).

MA46 can be synthesized by the synthesis method described in Patent Literature (WO2014/054785).

[Formula 18]

[Formula 19]

[Formula 20]

[Monomer (M2) having a structure that expresses only liquid crystal properties and a method for producing the same]

The monomer (M2) which has a structure which expresses only liquid crystallinity means the monomer which the polymer 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 may contribute to become a mesogenic structure independently, such as biphenyl and phenyl benzoate, and may also 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 21]

More specific examples of the monomer (M2) having a structure that expresses only liquid crystallinity include hydrocarbon, (meth)acrylate, itaconate, fumarate, maleate, α-methylene-γ-butyrolactone, styrene, vinyl, It is preferable that it is a structure having a polymerizable group composed of at least one selected from the group consisting of radically polymerizable groups such as maleimide and norbornene and siloxane, and a structure composed of at least one of the above formulas (21) to (31). Do.

The monomer (M2) has the above formulas MA2, MA9 to MA13, MA15, MA24, MA26, MA27, MA31, MA35, MA37, MA43 and MA45, and among those compounds, a polymerizable group of a compound having a methacrylate as a polymerizable group The group consisting of a compound substituted with a polymerizable group selected from the group consisting of acrylate, itaconate, fumarate, maleate, α-methylene-γ-butyrolactone, styrene, vinyl, maleimide, norbornene and siloxane It is preferable that it is at least 1 type selected from. In particular, it is preferable that a monomer (M2) has a (meth)acrylate as a polymeric group, Preferably, it is preferable that the terminal of a side chain is COOH, Preferably, for example.

[Monomer having a crosslinkable group (M3)]

(A) The polymer as component is (M-3) a monomer having a crosslinkable group, specifically the group consisting of the following formulas (G-1), (G-2), (G-3) and (G-4) a monomer having at least one group selected from (M3), more specifically a monomer having a structure represented by the following formula (0); may be formed with

[Formula 22]

(In formula (0), S, A, P, X, Q, B, T, l1 and l2 have the same meaning as defined in formula (1), and G is (G-1), ( G-2), (G-3) and (G-4) represents a group selected from, a broken line represents a bond, and R ⁵⁰ represents a group selected from a hydrogen atom, a halogen atom, an alkyl group having 1 to 3 carbon atoms, and a phenyl group. , and when there are two or more R ⁵⁰ , they may be the same or different from each other, t is an integer of 1 to 7, J represents O, S, NH or NR ⁵¹ , R ⁵¹ is an alkyl group having 1 to 3 carbon atoms or a phenyl group represents a group selected from)

[Monomer having a structure represented by Formula (0)]

More specific examples of the monomer having a structure represented by the formula (0) include hydrocarbon, (meth)acrylate, itaconate, fumarate, maleate, α-methylene-γ-butyrolactone, styrene, vinyl, maleate It is preferable to have a polymeric group comprised by at least 1 sort(s) selected from the group which consists of radical polymerizable groups, such as imide and norbornene, and siloxane, and to have a structure represented by said Formula (0).

Among such monomers, specific examples of the monomer having an epoxy group include glycidyl (meth) acrylate, (3,4-epoxycyclohexyl) methyl (meth) acrylate, and allyl glycidyl ether. Compounds such as these are mentioned, Among them, glycidyl (meth) acrylate, (3,4-epoxycyclohexyl) methyl (meth) acrylate, 3-ethenyl-7-oxabicyclo [4.1.0 ]heptane, 1,2-epoxy-5-hexene, 1,7-octadiene monoepoxyside, and the like.

Specific examples of the monomer having thiirane include those in which the epoxy structure of the monomer having an epoxy group is substituted with thiirane.

Specific examples of the monomer having an aziridine include those in which the epoxy structure of the monomer having an epoxy group is substituted with aziridine or 1-methylaziridine.

As a monomer which has an oxetane group, (meth)acrylic acid ester etc. which have an oxetane group are mentioned, for example. Among such monomers, 3-(methacryloyloxymethyl)oxetane, 3-(acryloyloxymethyl)oxetane, 3-(methacryloyloxymethyl)-3-methyl-oxetane, 3 -(acryloyloxymethyl)-3-methyl-oxetane, 3-(methacryloyloxymethyl)-3-ethyl-oxetane, 3-(acryloyloxymethyl)-3-ethyl-oxetane , 3-(methacryloyloxymethyl)-2-trifluoromethyloxetane, 3-(acryloyloxymethyl)-2-trifluoromethyloxetane, 3-(methacryloyloxymethyl) -2-phenyl-oxetane, 3-(acryloyloxymethyl)-2-phenyl-oxetane, 2-(methacryloyloxymethyl)oxetane, 2-(acryloyloxymethyl)oxetane; 2-(methacryloyloxymethyl)-4-trifluoromethyloxetane and 2-(acryloyloxymethyl)-4-trifluoromethyloxetane are preferable, and 3-(methacryloyloxy methyl)-3-ethyl-oxetane, 3-(acryloyloxymethyl)-3-ethyl-oxetane, and the like.

As a monomer which has a thietane group, the monomer by which the oxetane group of the monomer which has an oxetane group was substituted by the thietane group is preferable, for example.

As the monomer having an azetane group, for example, a monomer in which the oxetane group of the monomer having an oxetane group is substituted with an azetane group is preferable.

Among the above, the monomer which has an epoxy group, and the monomer which has an oxetane group from points, such as availability, are preferable, and the monomer which has an epoxy group is more preferable. Especially, the point of availability to glycidyl (meth)acrylate is preferable.

[Monomer having a nitrogen-containing aromatic heterocyclic group or the like (M4)]

The polymer (A1) and/or the polymer (A2) may optionally be (M-4) a monomer (M4) having at least one group selected from the group consisting of a nitrogen-containing aromatic heterocyclic group, an amide group and a urethane group; may be formed with

The nitrogen-containing aromatic heterocyclic ring is a structure selected from the group consisting of the following formulas [20a], [20b] and [20c] (wherein Z ₂ is a linear or branched alkyl group having 1 to 5 carbon atoms) It is preferable that it is an aromatic cyclic hydrocarbon containing at least 1 piece, Preferably 1 - 4 pieces.

[Formula 23]

Specifically, a pyrrole ring, an imidazole ring, an oxazole ring, a thiazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a quinoline ring, a pyrazoline ring, an isoquinoline ring, a carbazole ring, a purine ring, thiadia Sole ring, pyridazine ring, pyrazoline ring, triazine ring, pyrazolidine ring, triazole ring, pyrazine ring, benzimidazole ring, benzimidazole ring, chinoline ring, phenanthroline ring, indole ring, quinoc A saline ring, a benzothiazole ring, a phenothiazine ring, an oxadiazole ring, an acridine ring, etc. are mentioned. Furthermore, you may have a substituent containing a hetero atom at the carbon atom of these nitrogen-containing aromatic heterocyclic rings.

Among these, for example, a pyridine ring is preferable.

(A) By having a group selected from a nitrogen-containing aromatic heterocyclic group, an amide group, and a urethane group, the polymer as component (A) reduces the elution of ionic impurities when the polymer composition of the present invention is used as a liquid crystal aligning film; It is because it accelerates|stimulates the crosslinking reaction of the crosslinking|crosslinked group, more specifically, the crosslinking reaction of group represented by said Formula (0), or a more durable liquid crystal aligning film can be obtained. To prepare a polymer having a group selected from a nitrogen-containing aromatic heterocyclic group, an amide group and a urethane group, the monomer (M4) is the monomer (M1), a monomer having a structural unit represented by the formula (a), and a monomer (M2); What is necessary is just to copolymerize with a monomer (M3) as desired.

As the monomer (M4), a radical polymerizable group such as hydrocarbon, (meth)acrylate, itaconate, fumarate, maleate, α-methylene-γ-butyrolactone, styrene, vinyl, maleimide, norbornene, and It is preferable to have a structure which has a polymeric group comprised by at least 1 sort(s) selected from the group which consists of siloxane, nitrogen-containing aromatic heterocyclic group, an amide group, and a urethane group. NH of the amide group and the urethane group may not be substituted. As a substituent in the case of being substituted, an alkyl group, the protecting group of an amino group, a benzyl group, etc. are mentioned.

Among such monomers, as a monomer having a nitrogen-containing aromatic heterocyclic group, specifically, for example, 2-(2-pyridylcarbonyloxy)ethyl (meth)acrylate, 2-(3-pyridylcarr Bornyloxy)ethyl (meth)acrylate, 2-(4-pyridylcarbonyloxy)ethyl (meth)acrylate, etc. are mentioned.

Specific examples of the monomer having an amide group or a urethane group include, for example, 2-(4-methylpiperidin-1-ylcarbonylamino)ethyl(meth)acrylate, 4-(6-methacryloyl Iloxyhexyloxy)benzoic acid N-(tertbutyloxycarbonyl)piperidin-4-yl ester, 4-(6-methacryloyloxyhexyloxy)benzoic acid 2-(tertbutyloxycarbonyl) amino) ethyl ester and the like.

(M-4) The monomer (M4) having at least one group selected from the group consisting of a nitrogen-containing aromatic heterocyclic group, an amide group and a urethane group is a polymerizable group in the formulas MA6 to MA8 and MA33, and those compounds From the group consisting of acrylate, itaconate, fumarate, maleate, α-methylene-γ-butyrolactone, styrene, vinyl, maleimide, norbornene and siloxane, the polymerizable group of the compound having methacrylate as It is preferable that it is at least 1 sort(s) selected from the group which consists of the compound substituted by the polymeric group selected.

As mentioned above, it can copolymerize with other monomers in the range which does not impair the expression ability of photoreactivity and/or liquid crystal property. 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 acrylic rate, 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 rate, phenyl methacrylate, 2,2,2-trifluoroethyl methacrylate, tert-butyl methacrylate, cyclohexyl methacrylate, isobornyl methacrylate, 2-methoxyethyl methacrylate, Methoxytriethylene glycol methacrylate, 2-ethoxyethyl methacrylate, tetrahydrofurfuryl methacrylate, 3-methoxybutyl methacrylate, 2-methyl-2-adamantyl methacrylate, 2- and propyl-2-adamantyl methacrylate, 8-methyl-8-tricyclodecyl methacrylate, and 8-ethyl-8-tricyclodecyl methacrylate.

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, methyl styrene, chloro styrene, 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 the at least 2 types of polymers of this invention, The general-purpose method handled industrially can be used. Specifically, the monomer having a structural unit represented by the above formula (a), the photoreactive side chain monomer (M1) having a photoreactive moiety different from the photoreactive moiety represented by the formula (a), and the liquid crystalline side It can manufacture by cationic polymerization using the vinyl group of a chain monomer (M2), radical polymerization, or 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 more than decomposition temperature. 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 peroxycyclohexane, etc.), alkyl peresters (peroxyneodecanoic acid-tert-butyl ester, peroxypivalic acid-tert-butyl ester, peroxy 2-ethylcyclohexanoic acid-tert-amyl ester, etc.), and Sulfates (potassium persulfate, sodium persulfate, ammonium persulfate, etc.), azo compounds (azobisisobutyronitrile, 2,2'-di(2-hydroxyethyl) azobisisobutyronitrile, etc.) can be heard 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 radical photopolymerization initiators include benzophenone, Michler's ketone, 4,4'-bis(diethylamino)benzophenone, xanthone, thioxanthone, isopropylxanthone, and 2,4-diethylthiok. Santhone, 2-ethylanthraquinone, acetophenone, 2-hydroxy-2-methylpropiophenone, 2-hydroxy-2-methyl-4'-isopropylpropiophenone, 1-hydroxycyclohexylphenylketone, Isopropyl benzoin 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'-dimethoxy Styryl)-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-[p-N,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-dimethylamino Styryl)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'- Tetrakis (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 etc. are mentioned. 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.

A monomer (M1) having a structure that exhibits photoreactivity and liquid crystallinity; and (M-2) copolymerizing a monomer (M2) having a structure that expresses only liquid crystallinity to obtain each of the at least two types of polymers of the present invention as an organic solvent used in the reaction, particularly if the resulting polymer is dissolved not limited 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-methoxybutylpropionate, 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 and may be mixed and used. Moreover, the solvent which does not dissolve the produced|generated polymer may be sufficient, and you may use it in the range in which the produced|generated polymer does not precipitate, mixing with the organic solvent mentioned above.

In addition, since oxygen in the organic solvent inhibits the polymerization reaction in radical polymerization, 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. is preferably 1% by mass to 50% by mass, and more preferably 5% by mass to 30% by mass. The reaction initial stage can be performed at high concentration, and an organic solvent can be added after that.

In the radical polymerization reaction described above, 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 increases. It is preferable that it is -10 mol%. In addition, at the time of polymerization, various monomer components, a solvent, an initiator, etc. can also be added.

[Recovery of polymer]

What is necessary is just to inject|throw-in the reaction solution to a poor solvent and just to precipitate these polymers, when collect|recovering the produced|generated polymer from the reaction solution obtained by the reaction mentioned above. Examples of poor solvents 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 be heard 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, when 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 taken into consideration, 2000-200000 are preferable, More preferably, it is 5000-150000. Or the said weight average molecular weight becomes like this. Preferably it is 2000-1000000, More preferably, it is 5000-20000.

<<(B) 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 and may be mixed and used for them.

<<Optional Ingredients>>

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-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, 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-methoxymethyl propionate, 3-ethoxy methyl propionate Ethyl, 3-methoxyethyl propionate, 3-ethoxypropionic acid, 3-methoxypropionic acid, 3-methoxypropionate propyl, 3-methoxybutyl propionate, 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-mono Ethyl ether-2-acetate, dipropylene glycol, 2-(2-ethoxypropoxy)propanol, methyl lactate, ethyl lactate, lactic acid n-propyl ester, lactic acid n-butyl ester, lactic acid isoamyl ester, etc. Solvents with low surface tension, etc. can be heard

The number of these poor solvents may be one, and they may mix and use 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, a silicone type surfactant, a 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 Corporation), Sufflon (registered trademark) S-382, SC101, SC102, SC103, SC104, SC105, SC106 (manufactured by AGC Semichemical) ) 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-diazanonylacetate, 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.

Furthermore, 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, You may make it contain in a polymer composition. Although the specific phenoplast type additive is shown below, it is not limited to this structure.

[Formula 24]

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, neo Pentyl 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-diglycidylamino methyl)cyclohexane, N,N,N',N',-tetraglycidyl-4,4'-diaminodiphenylmethane, and the like are exemplified.

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 the mass part. 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 aromatic nitro compounds, coumarin (7-diethylamino-4-methylcoumarin, 7-hydroxy4-methylcoumarin), ketocoumarin, carbonylbiscoumarin, aromatic 2-hydroxyketone, and amino substituted, aromatic 2-hydroxyketones (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-dimethoxyphenylethanone) ), 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 the 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.

[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, as for the polymer composition used for this invention, the compound etc. which improve the adhesiveness of a liquid crystal aligning film and a board|substrate, the solvent and compound which improve the above-mentioned (A) component and the above-mentioned film thickness uniformity and surface smoothness, and a board|substrate are organic solvents It is preferably prepared as a solution dissolved in Here, as for content of (A) 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: Other polymers other than (A) component may be mixed in the range which does not impair liquid-crystal expression ability and photosensitive performance. 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 for such another polymer.

<The manufacturing method of the board|substrate which has a liquid crystal aligning film> and <The manufacturing method of a liquid crystal display element>

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

[I] (A) A side chain (a1) having a photoreactive moiety represented by the formula (a), a side chain (a2) having a photoreactive moiety different from the photoreactive moiety represented by the formula (a), and liquid crystallinity side chain type polymer which has a side chain (a3) which expresses; and

(B) 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 ultraviolet-ray which polarized to the coating film obtained by [I]; and

[III] A step 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.

2nd aspect of this invention WHEREIN: The manufacturing method of the board|substrate which has the liquid crystal aligning film of this invention,

[I] (A) A side chain (a1) having a photoreactive moiety represented by the formula (a), a side chain (a2) having a photoreactive moiety different from the photoreactive moiety represented by the formula (a), and liquid crystallinity side chain type polymer which has a side chain (a3) which expresses; and

(B) 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 ultraviolet-ray which polarized to the coating film obtained by [I]; and

[III] A step 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, in place of the substrate having the transverse electric field drive conductive film, a substrate not having the transverse electric field drive conductive film is used, and the above steps [I] to [III] (transverse electric field drive conduction In order to use the board|substrate which does not have a film|membrane, for convenience, in this application, by using the process [I'] - [III'] in some cases), the 2nd board|substrate which has a liquid crystal aligning film to which orientation control ability was provided is obtained by using 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 step [I], the polymer composition containing the photosensitive side chain type polymer|macromolecule which expresses liquid crystallinity in a predetermined temperature range, and an organic solvent is apply|coated on the board|substrate which has the electrically conductive film for lateral electric field drive, 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 acryl substrate and a polycarbonate substrate, etc. can be used.

In addition, in consideration of application to a reflective liquid crystal display device, an opaque substrate such as a silicon wafer may be used.

<Conductive film for lateral electric field drive>

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

Examples of the conductive film include, but are not limited to, ITO (Indium Tin Oxide: Indium Tin Oxide), IZO (Indium Zinc Oxide: Indium Zinc Oxide) and the like when the liquid crystal display element is a transmissive film.

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 an electrically conductive film on a board|substrate.

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 the polymer composition is applied on the substrate having a conductive film for lateral electric field drive, it is 50 to 200° C., preferably 50 to 150° C. by heating means such as a hot plate, 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 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 to 150 nm.

Moreover, it is also possible to provide the process of cooling the board|substrate on which the coating film was formed to room temperature after the [I] process before the subsequent [II] process.

<Process [II]>

In process [II], the polarized ultraviolet-ray is irradiated to the coating film obtained by process [I]. 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 or the like according to the type of coating film to be used. And, for example, in order to selectively cause a photocrosslinking reaction, an ultraviolet ray having a wavelength of 290 nm to 400 nm may be selected and used. As the ultraviolet, for example, light emitted from a high-pressure mercury lamp can be used.

The irradiation amount of the polarized ultraviolet rays depends on the coating film to be used. The irradiation amount is 1% of the amount of polarized ultraviolet rays 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 rays and the ultraviolet absorbance in the perpendicular direction in the coating film It is preferable to set it as in the range of -70%, and it is more preferable to set it in the range of 1% - 50%.

<Process [III]>

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

Heating can use heating means, such as a hot plate, a heat circulation type oven, or an IR (infrared) type|mold 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, the liquid crystal expression temperature of the coating film surface is expected to be 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, as for heating temperature, it is more preferable to exist in the temperature range of the liquid crystalline expression temperature of the coating-film surface. That is, the temperature range of the heating temperature after polarization|polarized-light ultraviolet irradiation makes the temperature 10 degreeC lower than the lower limit of the temperature range of the liquid crystal expression temperature of the side chain type polymer|macromolecule to be used as a lower limit, The temperature 10 degreeC lower than the upper limit of the liquid crystal temperature range It is preferable that it is a temperature in the range which makes the upper limit. 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 excessively higher than the above temperature range, the state of the coating film 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 the surface of the coating film undergoes phase transition from the solid phase to the liquid crystal phase, and iso that causes a phase transition from the liquid crystal phase to the isotropic phase (isotropic phase). It refers to a temperature below the tropic phase transition temperature (Tiso).

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 with a liquid crystal aligning film can be manufactured with high efficiency.

<Process [IV]>

[IV] Process does not have 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] similarly It is the process of opposingly arrange|positioning the board|substrate with a liquid crystal aligning film (2nd board|substrate) which does not have it through a liquid crystal so that both liquid crystal aligning films may oppose, produce a liquid crystal cell by a well-known method, and produce a transverse electric field drive type liquid crystal display element. . Further, in the steps [I'] to [III'], in the step [I], instead of the substrate having the conductive film for driving the lateral electric field, a substrate without the conductive film for lateral electric field driving was used, and the process [ I] to [III] can be carried out in the same manner. 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 the production of a liquid crystal cell or a liquid crystal display element, the above-mentioned first and second substrates are prepared, a spacer is dispersed on the liquid crystal aligning film of one side of the substrate, the liquid crystal aligning film surface is inside, and another A method in which one side of the substrate is bonded and a liquid crystal is injected under reduced pressure to seal, or a method in which a liquid crystal is dripped onto the liquid crystal aligning film surface on which a spacer is dispersed, and a method in which the substrate is bonded and sealed can be exemplified. there is. 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, and more preferably 2 µm to 10 µm. The spacer diameter determines the distance between the pair of substrates that sandwich the liquid crystal layer, that is, the thickness of the liquid crystal layer.

After the manufacturing method of the board|substrate with a coating film of this invention apply|coats a polymer composition on a board|substrate and forms a coating film, it irradiates the ultraviolet-ray which polarized. Next, by heating, highly efficient anisotropic introduction|transduction to a side chain type polymer film|membrane is implement|achieved, and the board|substrate with a 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.

Therefore, the coating film used for the method of this invention can be set as the liquid-crystal aligning film excellent in the orientation control ability with highly efficient anisotropy introduce|transduced by performing irradiation of the ultraviolet-ray polarized 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 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 optimal dose of polarized UV light for the introduction of highly efficient anisotropy to the coating film used in the present invention is that of polarized UV light that optimizes the amount of photosensitive group photocrosslinking reaction, photoisomerization reaction, or optical Fris dislocation reaction in the coating film. corresponding to the amount of irradiation. 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 for this invention, when polarized ultraviolet-ray is irradiated with respect to the structure which has a photocrosslinkable group, when the photosensitive group of the side chain to crosslink reacts excessively, the crosslinking reaction between side chains will advance 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 Fleece potential 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 hindrance of advancing of the self-assembly by subsequent heating. In addition, when polarized ultraviolet rays are irradiated with respect to a structure having an optical Fris dislocation group, if the irradiation amount of ultraviolet rays is too large, the side chain polymers are photodecomposed and the progress of self-organization by subsequent heating is hindered. there is.

Therefore, in the coating film used in the present invention, the optimal amount of the photosensitive group of the side chain by irradiation of polarized ultraviolet light is a photocrosslinking reaction, a photoisomerization reaction, or an optical Fris rearrangement reaction, the optimal 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 a 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 the present invention, the amount of photocrosslinking reaction or photoisomerization reaction of the photosensitive group in the side chain of the side chain polymer film, or the photo Fris rearrangement reaction by optimization of the irradiation amount of polarized ultraviolet light Optimize. And the anisotropic introduction|transduction with respect to the coating film used for this invention with high efficiency is implement|achieved together with subsequent heat processing. 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, with respect to the coating film used for this invention, the ultraviolet absorption in the direction parallel to the polarization direction of the polarized ultraviolet-ray after polarized-ultraviolet irradiation and the ultraviolet absorption in a perpendicular direction are measured, respectively. 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 light 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 ultraviolet-ray which polarized in 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 polarized ultraviolet-ray which implement|achieves ΔAmax, and 1% to 50% of It is more preferable to set it as within the range. The coating film used for this invention WHEREIN: The irradiation amount of the polarization|polarized-light ultraviolet-ray within 1% - 50% of the range of the quantity of the polarization|polarized-light ultraviolet-ray which implement|achieves (DELTA)Amax is 0.1 mol% - 20 mol% of the whole photosensitive group which the side chain type polymer film has It corresponds to the amount of polarized ultraviolet light that undergoes a photocrosslinking reaction.

From the above, in the manufacturing method of this invention, in order to implement|achieve highly efficient anisotropic introduction to a coating film, it is preferable 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. Do. 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 the temperature of the heating 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. can be used readily.

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

Example

M1 and M2 as a monomer having a photoreactive group used in Examples, M3 as a monomer having a liquid crystalline group, HBAGE as a monomer having a crosslinking group, and A1 as a monomer having an amide group are shown below.

M1, M2, and M3 were synthesized as follows, respectively. That is, M1 was synthesize|combined by the synthesis method described in patent document (WO2011-084546). M2 was synthesized by the synthesis method described in the patent document (WO2014/054785 pamphlet). M3 was synthesized by the synthesis method described in the patent document (Unexamined-Japanese-Patent No. 9-118717). In addition, a polymer formed by using M1 as a monomer has photoreactivity and liquid crystallinity, and a polymer formed by using M3 as a monomer has only liquid crystallinity.

The monomer A1 to be copolymerized was synthesized by the synthesis method described in the patent document (WO2014/054785 pamphlet).

As HBAGE (hydroxybutyl acrylate glycidyl ether), a commercially available thing was used.

[Formula 25]

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

(diisocyanate component)

ISPDA: isophorone diisocyanate

(diamine component)

DDM: 4,4'-diaminodiphenylmethane

Me-4APhA: N-methyl-2-(4-aminophenyl)ethylamine

Me-DADPA: 4,4'-diaminodiphenyl (N-methyl) amine

(tetracarboxylic dianhydride)

TDA: 3,4-dicarboxy-1,2,3,4-tetrahydro-1-naphthalenesuccinic dianhydride

(organic solvent)

THF: tetrahydrofuran

NMP: N-ethyl-2-pyrrolidone

BCS : Butyl Cellosolve

(Polymerization Initiator)

AIBN: 2,2'-azobisisobutyronitrile

<Photo-alignment polymer synthesis example P1>

M1 (2.99 g: 0.15 mol%), M2 (1.31 g: 0.05 mol%), and M3 (14.71 g: 0.80 mol%) were dissolved in NMP (79.21 g), degassed with a diaphragm pump, and then AIBN ( 0.30 g) was added and degassed again. Then, it was made to react at 60 degreeC for 8 hours, and the polymer solution of the methacrylate was obtained. This polymer solution was dripped at methanol (450 ml), and the obtained deposit was filtered. This deposit was washed with methanol and dried under reduced pressure to obtain methacrylate polymer powder P1.

<Photo-alignment polymer synthesis examples P2 to P3>

Except having used the composition shown in Table 1, the method similar to the photo-alignment polymer synthesis example P1 was used and the methacrylate polymer powder P2-P3 was synthesize|combined.

<Polymer Synthesis Example L1>

As a tetracarboxylic dianhydride component, it is 4.85 g and a diisocyanate component for TDA as 3.67 g and a diamine component for DDM 5.89 g, Me-DADPA 0.35 g, Me-4APhA 0.25 g is used, and Me-4APhA is used, NMP In 85.06 g, it was made to react at room temperature for 18 hours, and the solution of the density|concentration of 15 wt% of a polyamic acid (L1) was obtained.

<Example 1>

The methacrylate polymer powder P1 (1.2g) obtained by the photo-alignment polymer synthesis example P1 was added to NMP (12.8g), and it stirred at room temperature for 1 hour, and it was made to melt|dissolve. Then, polymer solution T1 was obtained by adding and stirring BCS (6.0g). This polymer solution T1 was made into the liquid crystal aligning agent for forming a liquid crystal aligning film as it is.

<Example 2>

The methacrylate polymer powder P1 (0.36g) obtained by the photo-alignment polymer synthesis example P1 was added to NMP (8.04g), and it stirred at room temperature for 1 hour, and it was made to melt|dissolve. Polyamic-acid solution L1 (5.6g) and BCS (6.0g) obtained by polymer synthesis example L1 were added to this solution, and polymer solution T2 was obtained by stirring. This polymer solution T2 was made into the liquid crystal aligning agent for forming a liquid crystal aligning film as it is.

<Control 1>

The methacrylate polymer powder P2 (1.2g) obtained by the photo-alignment polymer synthesis example P2 was added to NMP (12.8g), and it stirred at room temperature for 1 hour, and it was made to melt|dissolve. Then, polymer solution CT1 was obtained by adding and stirring BCS (6.0g). This polymer solution CT1 was made into the liquid crystal aligning agent for forming a liquid crystal aligning film as it is.

<Control 2>

The methacrylate polymer powder P3 (1.2g) obtained by the photo-alignment polymer synthesis example P3 was added to NMP (12.8g), and it stirred at room temperature for 1 hour, and it was made to melt|dissolve. Then, polymer solution CT2 was obtained by adding and stirring BCS (6.0g). This polymer solution CT2 was made into the liquid crystal aligning agent for forming a liquid crystal aligning film as it is.

<Control 3>

The methacrylate polymer powder P2 (0.36g) obtained by the photo-alignment polymer synthesis example P2 (0.36g) was added to NMP (8.04g), and it stirred at room temperature for 1 hour, and it was made to melt|dissolve. Polyamic acid solution L1 (5.6g) and BCS (6.0g) obtained by polymer synthesis example L1 were added to this solution, and polymer solution CT3 was obtained by stirring. This polymer solution CT3 was made into the liquid crystal aligning agent for forming a liquid crystal aligning film as it is.

<Control 4>

The methacrylate polymer powder P3 (0.36 g) obtained by the photo-alignment polymer synthesis example P3 was added to NMP (8.04 g), and it stirred at room temperature for 1 hour, and was made to melt|dissolve. Polyamic acid solution L1 (5.6g) and BCS (6.0g) obtained by polymer synthesis example L1 were added to this solution, and polymer solution CT4 was obtained by stirring. This polymer solution CT4 was made into the liquid crystal aligning agent for forming a liquid crystal aligning film as it is.

About liquid crystal aligning agent T1-2 of Examples 1-2, and liquid crystal aligning agent CT1-CT4 of controls 1-4, the polymer type used, its content, other polymer content and solvent, and its content are Table 2 below arrange in

<Production of liquid crystal cell>

After filtering the liquid crystal aligning agent (T1) obtained in Example 1 with a 0.45 micrometer filter, spin-coat on the glass substrate with a transparent electrode, and after drying for 90 second on a 70 degreeC hotplate, a liquid crystal aligning film with a film thickness of 100 nm was formed. Then, after irradiating 5-30 mJ/cm<2> of 313 nm ultraviolet-ray to the coating-film surface through a polarizing plate, it heated with a 150 degreeC hotplate for 10 minutes, and obtained the board|substrate with a liquid crystal aligning film. After preparing two such substrates with a liquid crystal aligning film, and installing a 6 µm spacer on the liquid crystal aligning film surface of one substrate, the two substrates are combined so that the rubbing directions are parallel, leaving the liquid crystal injection port and sealing the periphery Thus, an empty cell having a cell gap of 4 µm was produced. Liquid crystal MLC-3019 (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 which the liquid crystal aligned parallelly was obtained.

Similarly, the liquid crystal cell was manufactured using liquid crystal aligning agent T2 obtained in Example 2, and liquid crystal aligning agent CT1-4 obtained by the controls 1-4.

<Orientation evaluation>

The liquid crystal cell prepared in Examples 1 to 2 and Controls 1 to 4 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 luminance of the transmitted light is the smallest. The placement angle of the was adjusted. The liquid crystal cell was visually confirmed. If this liquid crystal cell orientated favorably and flow orientation was not confirmed, "(circle)" and it orientated, but when flow orientation was confirmed, it was set as "x" if it was "(triangle|delta)" and no orientation.

<Voltage retention rate (VHR) evaluation>

Using the liquid crystal cell prepared above, a voltage of 5 V was applied for 60 μs under a temperature of 70° C., the voltage 16.67 ms after was measured, and how much the voltage was maintained was calculated as a voltage retention (VHR). In addition, voltage retention measuring apparatus VHR-1 by the Toyo Technica company was used for the measurement of voltage retention.

The result of VHR of Examples 1-2 and Control 1-4 is shown in Table 3 together with the result of <Orientation evaluation> and "total amount of photoreactive groups" in the photo-alignment polymer component.

From Table 2, in Examples 1 and 2, by copolymerizing a monomer having two different types of photoreactive groups, a better orientation is shown in a wide range of UV irradiation dose than a polymer copolymerized alone, respectively, and a polyamic acid is further blended By doing so, it can be seen that the VHR is improved.

Claims (7)

(A) A side chain (a1) having a photoreactive moiety represented by the following formula (a), a side chain (a2) having a photoreactive moiety different from the photoreactive moiety represented by the following formula (a), and liquid crystallinity are expressed Side chain type polymer|macromolecule which has a side chain (a3) to say; and
(B) organic solvent
As a polymer composition containing,
[Formula 1]

The said side chain (a2) is following formula (2)
(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-;
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 a C1-C12 alkylene group, and the hydrogen atom couple|bonded with them may be substituted by the halogen group;
Y ₂ is a group selected from the group consisting of a divalent benzene ring, a naphthalene ring, a furan ring, a pyrrole ring, an alicyclic hydrocarbon having 5 to 8 carbon atoms, and combinations thereof, and the hydrogen atoms bonded thereto are each independently - NO2, -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;
R represents a hydroxyl group or an alkoxy group having 1 to 6 carbon atoms, or 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 a group formed by bonding the same or different 2 to 6 rings selected from their substituents through a bonding group B, and the hydrogen atoms bonded thereto are each independently -COOR ₀ (wherein R ₀ is a hydrogen atom or represents an alkyl group having 1 to 5 carbon atoms), -NO ₂ , -CN, -CH=C(CN) ₂ , -CH=CH-CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms It may be substituted with an oxy group;
X is a single bond, -COO-, -OCO-, -N=N-, -CH=CH-, -C≡C-, -CH=CH-CO-O-, or -O-CO-CH= When CH- is represented and the number of X becomes 2, X may be same or different;
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; However, when X is -CH=CH-CO-O- or -O-CO-CH=CH-, P or Q on the side to which -CH=CH- is bonded is an aromatic ring, and the number of P is 2 or more When it becomes, P may be 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)
As any 1 type of photosensitive side chain selected from the group which consists of
The main chain of side chain type polymer|macromolecule is following formula PL-1 - PL-5
(In formulas PL-1 to PL-5, R ¹ , R ² , and R ³ are a hydrogen atom, a linear or branched alkyl group having 1 to 10 carbon atoms, or a straight chain having 1 to 10 carbon atoms substituted with halogen or A composition obtained from a polymerizable group selected from the group consisting of) a branched chain alkyl group.
[Formula 2]

The method of claim 1,
The said side chain (a3) is following formula (21)-(31)
(Wherein, A and B are each independently a single bond, -O-, -CH ₂ -, -COO-, -OCO-, -CONH-, -NH-CO-, -CH=CH-CO-O - or -O-CO-CH=CH-;
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, nitrogen-containing A heterocyclic ring, a C5-C8 alicyclic hydrocarbon, a C1-C12 alkyl group, or a C1-C12 alkoxy group is represented;
As for q1 and q2, one is 1 and the other is 0;
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, 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, an alicyclic hydrocarbon having 5 to 8 carbon atoms, an alkyl group, or an alkyl represents an oxy group;
Z ₁ , Z ₂ represents a single bond, -CO-, -CH ₂ O-, -CH=N- or -CF ₂ -)
The composition which is any 1 type of liquid crystalline side chain selected from the group which consists of.
[Formula 3]

[I] A step of forming a coating film by applying the composition according to claim 1 or 2 on a substrate having a conductive film for lateral electric field drive;
[II] The process of irradiating the ultraviolet-ray which polarized to the coating film obtained by [I]; and
[III] A step 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 the liquid crystal aligning film for lateral electric field drive type liquid crystal display elements manufactured by the method of Claim 3. The lateral electric field drive type liquid crystal display element which has the board|substrate of Claim 4. [I] A step of forming a coating film by applying the composition according to claim 1 or 2 on a substrate having a conductive film for lateral electric field drive;
[II] The process of irradiating the ultraviolet-ray which polarized to the coating film obtained by [I]; and
[III] A step of heating the coating film obtained in [II];
Process of preparing the 1st board|substrate which has the liquid crystal aligning film for lateral electric field drive type liquid crystal display elements to which orientation control ability was provided obtained by having;
[I'] The process of apply|coating the polymer composition of Claim 1 or 2 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'] A step of heating the coating film obtained in [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] Process of opposingly arrange|positioning the 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 6 .