TW201522384A - Method for manufacturing substrate having liquid crystal alignment film for in-plane-switching-type liquid crystal display element - Google Patents

Abstract

The present invention provides a highly efficient in-plane-switching-type liquid crystal display element endowed with alignment controllability and having excellent ghosting characteristics. The present invention provides a method for manufacturing a substrate having a liquid crystal alignment film, the method having: [I] a step for applying, on a substrate having a conductive film for in-plane switching, a polymer composition containing (A) a photosensitive side-chain polymer exhibiting liquid crystal properties in a predetermined temperature range, (B) di-isobutyl carbinol, and (C) an organic solvent and forming a coating film; [II] a step for irradiating the coating film obtained in [I] with polarized ultraviolet rays; and [III] a step for heating the coating film obtained in [II]; whereby is obtained a liquid crystal alignment film for an in-plane-switching-type liquid crystal display element endowed with alignment controllability.

Description

Method for manufacturing substrate having liquid crystal alignment film for transverse electric field drive type liquid crystal display element

The present invention relates to a method of producing a substrate having a liquid crystal alignment film for a lateral electric field drive type liquid crystal display device. More specifically, it relates to a novel method for producing a liquid crystal display element having a liquid crystal alignment film which is excellent in image retention characteristics, has high linearity at the end portion, and has a small ridge at the end.

The liquid crystal display element is known as a display device which is lightweight, thin, and low in power consumption, and has been in an amazing development in recent years for use in large-scale television applications. The liquid crystal display element is configured by, for example, arranging a liquid crystal layer on a transparent substrate by one of the electrodes. Further, in the liquid crystal display device, an organic film made of an organic material is used as the liquid crystal alignment film so that the liquid crystal becomes a desired alignment state between the substrates.

In other words, the constituent members of the liquid crystal alignment film-type liquid crystal display device are formed on a surface adjacent to the liquid crystal of the substrate on which the liquid crystal is sandwiched, and serve to make the liquid crystal alignment between the substrates in a certain direction. Further, the liquid crystal alignment film may require a role of controlling the pretilt angle of the liquid crystal in addition to the role of aligning the liquid crystal in a certain direction such as a direction parallel to the substrate. The ability to control liquid crystal alignment in such a liquid crystal alignment film (hereinafter referred to as The alignment control energy is imparted by the alignment treatment of the organic film constituting the liquid crystal alignment film.

As a method of aligning the liquid crystal alignment film for imparting alignment control energy, a rubbing method has been known in the past. The rubbing method is to rub (friction) the surface of the polyvinyl alcohol or the organic film such as polyimide or polyimide on the substrate with a cloth such as cotton, nylon or polyester to make the liquid crystal in the wiping direction ( Friction direction) method of alignment. This rubbing method is used in the manufacturing process of a conventional liquid crystal display element because the liquid crystal alignment state can be realized easily and relatively stably. In addition, as the organic film used for the liquid crystal alignment film, a polyimide-based organic film having excellent reliability such as heat resistance and electrical properties is selected.

However, the rubbing method of wiping the surface of the liquid crystal alignment film formed of polyimide or the like has a problem of generating dust or static electricity. Further, in recent years, the surface of the liquid crystal alignment film cannot be uniformly wiped with a cloth due to the high definition of the liquid crystal display element or the unevenness caused by the switching of the active element by the electrode on the substrate or the liquid crystal driving. Sometimes it is impossible to achieve uniform liquid crystal alignment.

Therefore, the photo-alignment method is actively reviewed as another alignment treatment method of the liquid crystal alignment film which does not rub.

There are various methods for the photo-alignment method. However, linear light or collimate light is used in the organic film constituting the liquid crystal alignment film to form an anisotropy, and the liquid crystal is aligned according to the anisotropy.

As a main light alignment method, a decomposition type photoalignment method is known. For example, the polyimine film is irradiated with polarized ultraviolet light, and the molecular structure is utilized. The polarization direction of the ultraviolet light is absorbed and the decomposition of the opposite direction is generated. In addition, the liquid crystal is aligned by the polyimine which remains without decomposition (refer to, for example, Patent Document 1).

Further, a photo-alignment type or a photo-isomerization type photo-alignment method is also known. For example, polyvinyl cinnamate is used, and a polarized ultraviolet ray is irradiated, and a dimerization reaction (crosslinking reaction) is generated in a double bond portion of two side chains parallel to the polarized light. Next, the liquid crystal is aligned in a direction orthogonal to the polarization direction (see, for example, Non-Patent Document 1). Further, when a side chain type polymer having an azobenzene in a side chain is used, a polarized ultraviolet ray is irradiated, and an isomerization reaction occurs in the azobenzene portion of the side chain parallel to the polarized light, so that the liquid crystal is orthogonal to the polarization direction. Directional alignment (refer to, for example, Non-Patent Document 2).

As described above, the alignment treatment method of the liquid crystal alignment film by the photo-alignment method does not require rubbing, and there is no doubt that dust or static electricity is generated. Further, even in the case of a substrate having a liquid crystal display element having irregularities on its surface, an alignment treatment can be applied to form an alignment treatment method of a liquid crystal alignment film which is suitable for industrial production processes.

Further, when a liquid crystal alignment agent (also referred to as a "coating solution") to be used for forming a liquid crystal alignment film is applied to a substrate, it is generally industrially performed by a flexographic printing method, an inkjet coating method, or the like. In this case, in addition to N-methyl-2-pyrrolidone or γ -butyrolactone, which is a solvent (also referred to as "good solvent") which is excellent in solubility in a resin, in the solvent of the coating solution, In order to improve the uniformity of the coating film of the liquid crystal alignment film, butyl cellosolve or the like which is a solvent having a low solubility in a resin (also referred to as a "weak solvent") (see, for example, Patent Document 2) .

[Previous Technical Literature] [Patent Literature]

[Patent Document 1] Japanese Patent No. 3893659

[Patent Document 2] Japanese Patent Laid-Open No. Hei 2-37324

[Non-patent literature]

[Non-Patent Document 1] M. Shadt et al., Jpn. J. Appl. Phys. 31, 2155 (1992).

[Non-Patent Document 2] K. Ichimura et al., Chem. Rev. 100, 1847 (2000).

As described above, the photo-alignment method is an alignment treatment method for a liquid crystal display element, and has a large advantage in that it does not require the rubbing step itself as compared with the rubbing method which has been industrially used in the past. Further, the optical alignment method can change the irradiation amount of the polarized light to control the alignment control energy as compared with the friction method in which the alignment control energy is substantially constant by friction. However, when the optical alignment method achieves the same degree of alignment control energy as in the case of using the rubbing method, a large amount of polarized light irradiation amount is required, and there is a case where stable liquid crystal alignment cannot be achieved.

For example, the decomposition type light described in the above Patent Document 1 In the alignment method, it is necessary to irradiate the polyimide film with ultraviolet light from a high-pressure mercury lamp outputting 500 W for 60 minutes, etc., and it is necessary to irradiate a large amount of ultraviolet rays for a long time. Further, in the case of the dimerization type or the photoisomerization type photoalignment method, a large amount of ultraviolet rays of several J (Joules) to several tens of J may be required. In addition, in the photo-alignment type or the photo-isomerization type photo-alignment method, since the thermal stability or the light stability of the liquid crystal alignment is poor, when it is a liquid crystal display element, there is a problem of alignment failure or display of image sticking. . In particular, since the liquid crystal molecules of the lateral electric field drive type are switched in-plane, the alignment of the liquid crystal is likely to occur after the liquid crystal is driven, and the image sticking due to the AC drive is a problem.

Therefore, in the photo-alignment method, it is required to achieve high-efficiency or stable liquid crystal alignment of the alignment treatment, and it is required to efficiently perform a liquid crystal alignment film or a liquid crystal alignment agent which imparts high alignment control energy to the liquid crystal alignment film.

Further, in recent years, liquid crystal display elements have been oriented to portable applications such as smart phones or mobile phones. In order to ensure as many display interfaces as possible, the sealant (which is used to adhere the substrate between the liquid crystal display elements) is placed in close proximity to the end of the liquid crystal alignment film. Therefore, the coating property of the end portion of the liquid crystal alignment film is lowered, that is, when the end portion of the liquid crystal alignment film is not straight, or the end portion is in a raised state, the adhesion between the sealant and the substrate is lowered. There is a case where the display characteristics or reliability of the liquid crystal display element are lowered.

SUMMARY OF THE INVENTION An object of the present invention is to provide an alignment control energy with high efficiency, excellent afterimage characteristics, high linearity at an end portion, and ridge of an end portion. A substrate having a liquid crystal alignment film for a lateral electric field drive type liquid crystal display device and a lateral electric field drive type liquid crystal display device having the substrate.

The results of a positive review by the team of the present invention to achieve the above problems revealed the following inventions.

<1> A polymer composition, particularly a composition for producing a liquid crystal alignment film for a transverse electric field-driven liquid crystal display device, which comprises a polymer composition of the following composition [I]: (A) at a specific temperature range A photosensitive side chain type polymer exhibiting liquid crystallinity, (B) diisobutyl carbinol, and (C) an organic solvent.

<2> In the above <1>, the component (A) preferably has a photosensitive side chain which causes photocrosslinking, photoisomerization, or Fries rearrangement.

<3> In the above <1> or <2>, the component (A) preferably has any photosensitive side chain selected from the group consisting of the following formulas (1) to (6):

Wherein A, B and D each independently represent a single bond, -O-, -CH ₂ -, -COO-, -OCO-, -CONH-, -NH-CO-, -CH=CH-CO-O- Or -O-CO-CH=CH-; S is an alkylene group having 1 to 12 carbon atoms, and the hydrogen atom bonded to the hydrogen atom may be substituted with a halogen group; T is a single bond or a carbon number of 1 to 12 An alkyl group, and a hydrogen atom bonded to the hydrogen atom may be substituted with a halogen group; Y ₁ represents a benzene ring selected from a monovalent group, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring, and a carbon number of 5-8 The ring of the alicyclic hydrocarbon or the group of the same or different 2 to 6 ring systems selected from the substituents bonded through the bonding group B, and the hydrogen atoms bonded to the hydrogen atoms may be 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, carbon The alkyl group having 1 to 5 or the alkyl group having 1 to 5 carbon atoms is substituted; the Y ₂ is selected from the group consisting of a divalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring, and a carbon number of 5~ a group of 8 alicyclic hydrocarbons, and a combination of such groups, and the hydrogen atoms bonded to the groups may be independently independently -NO ₂ , -CN, -CH=C(CN) ₂ , -CH =CH-CN, halo, alkyl 1 to 5, or carbon The alkyl group substituted with 1 to 5; R & lt represents a hydroxyl group, an alkoxy group having a carbon number of 1 to 6, or represents the same as defined in the Y _1; X represents a single bond, -COO -, - OCO -, - N = N-, -CH=CH-, -C≡C-, -CH=CH-CO-O-, or -O-CO-CH=CH-, X may be the same or different when X is 2; Cou represents a coumarin-6-yl or coumarin-7-yl group, and the hydrogen atoms bonded to the hydrogen atoms may be independently independently -NO ₂ , -CN, -CH=C(CN) ₂ , -CH= CH-CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or an alkyloxy group having 1 to 5 carbon atoms; one of q1 and q2 is 1 and the other is 0; q3 is 0 or 1 And P and Q are each independently 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 a combination thereof. However, when X is -CH=CH-CO-O-, -O-CO-CH=CH-, P or Q on the side of the bond of -CH=CH- is an aromatic ring, and the number of P is 2 or more. When P is equal to or different from each other, Q may be the same or different when Q is 2 or more; 11 is 0 or 1; 12 is an integer of 0 to 2; when both 11 and 12 are 0, T is A also indicates a single button when a single button is used; when 11 is 1, B is also a single bond when T is a single bond; H and I are each independent Is selected from the divalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring, and the group of combinations of these.

<4> In any one of <1> to <3>, the component (A) preferably has any photosensitive side chain selected from the group consisting of the following formulas (7) to (10):

In the formula, A, B, D, Y ₁ , X, Y ₂ , and R have the same definitions as above; l represents an integer from 1 to 12; m represents an integer from 0 to 2, and m1 and m2 represent 1 to 3; Integer; n represents an integer from 0 to 12 (but B is a single bond when n=0).

<5> In any one of <1> to <3>, the component (A) preferably has any photosensitive side chain selected from the group consisting of the following formulas (11) to (13):

In the formula, A, X, l, m, m2 and R have the same definitions as described above.

<6> In any one of <1> to <3>, the component (A) preferably has a photosensitive side chain represented by the following formula (14) or (15):

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

<7> In any one of <1> to <3>, the component (A) preferably has a photosensitive side chain represented by the following formula (16) or (17):

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

<8> In any one of <1> to <3>, the component (A) preferably has a photosensitive side chain represented by the following formula (18) or (19):

In the formula, A, B, Y ₁ , q1, q2, m1, and m2 have the same definitions as described 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 alkyl group having 1 to 5 carbon atoms. Oxygen.

<9> In any one of <1> to <3>, the component (A) preferably has a photosensitive side chain represented by the following formula (20):

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

<10> In any one of <1> to <9>, the component (A) preferably has any one of liquid crystal side chains selected from the group consisting of the following formulas (21) to (31):

In the formula, A, B, q1 and q2 have the same definitions as above; Y ₃ is selected from the group consisting of a monovalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a nitrogen-containing hetero ring and a carbon number 5-8. a group of a cyclic hydrocarbon, and a combination of the groups, wherein the hydrogen atoms bonded to the hydrogen atoms may be independently -NO ₂ , -CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or a carbon number Substituted by an alkyl group of 1 to 5; R ₃ represents a hydrogen atom, -NO ₂ , -CN, -CH=C(CN) ₂ , -CH=CH-CN, a halogen group, a monovalent benzene ring, naphthalene a ring, a biphenyl ring, a furan ring, a nitrogen-containing hetero ring, an alicyclic hydrocarbon having 5 to 8 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms; and 1 represents 1 to 12 In the integer, m represents an integer from 0 to 2, but in the formulas (25) to (26), the total of all m is 2 or more, and in the formulas (27) to (28), the total of all m is 1 or more, and m1. M2 and m3 each independently represent an integer of 1 to 3; R ₂ represents 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 hetero ring, and An alicyclic hydrocarbon having 5 to 8 carbon atoms; and an alkyl group or an alkyloxy group; Z ₁ and Z ₂ represent a single bond, -CO-, -CH ₂ O-, -CH=N-, -CF ₂ -.

<11> A method for producing a substrate having a liquid crystal alignment film, wherein the liquid crystal alignment film is obtained by a liquid crystal alignment film for a lateral electric field drive type liquid crystal display element which imparts alignment control energy by the following steps: [I] The composition of any one of the above-mentioned <1> to <10>, in particular, a composition for producing a liquid crystal alignment film for a lateral electric field-driven liquid crystal display device, which is formed on a substrate having a conductive film for driving a transverse electric field. Coating film a step of [II] irradiating the polarized ultraviolet light to the coating film obtained in [I]; and [III] a step of heating the coating film obtained in [II].

<12> A substrate having a liquid crystal alignment film for a transverse electric field drive type liquid crystal display device produced by the method of the above <11>.

<13> A transverse electric field drive type liquid crystal display element having the substrate of the above <12>.

<14> A method of producing a liquid crystal display device, comprising: obtaining a lateral electric field drive type liquid crystal display element by the following steps: preparing a substrate (first substrate) as described in <12> above; obtaining a liquid crystal alignment film In the step of the second substrate, the liquid crystal alignment film imparting the alignment control energy is obtained by the following steps [I'] to [III']: [I'] is coated on the second substrate as described above <1>~ The composition of any one of <10>, in particular, a step of forming a coating film for a composition for producing a liquid crystal alignment film for a lateral electric field-driven liquid crystal display device; [II'] irradiating the coating film obtained in [I'] a step of polarizing ultraviolet rays; and [III'] a step of heating the coating film obtained in [II']; and [IV] a step of obtaining a liquid crystal display device, wherein the first and second substrates are interposed by liquid crystal The first and second substrates are arranged to face each other in such a manner that the liquid crystal alignment film faces each other.

<15> A lateral electric field driven liquid crystal display element, It is produced by the method of <14> mentioned above.

According to the present invention, it is possible to provide a substrate having a liquid crystal alignment film for a lateral electric field drive type liquid crystal display device which is excellent in image retention performance and excellent in image retention characteristics, and a lateral electric field drive type liquid crystal display device having the substrate.

Since the transverse electric field drive type liquid crystal display element manufactured by the method of the present invention can impart the alignment control energy with high efficiency, the display characteristics are not impaired even if it is continuously driven for a long period of time.

Further, the liquid crystal alignment agent of the present invention can provide a liquid crystal alignment film having a high linearity at the end portion of the liquid crystal alignment film and a small rise in the end portion of the liquid crystal alignment film.

1‧‧‧Side chain polymer film

2, 2a‧‧‧ side chain

3‧‧‧Side chain polymer film

4, 4a‧‧‧ side chain

5‧‧‧Side chain polymer film

6, 6a‧‧‧ side chain

7‧‧‧Side chain polymer film

8, 8a‧‧‧ side chain

9‧‧‧Liquid alignment film

10‧‧‧ITO (Indium Tin Oxide) evaporation substrate

11‧‧‧Liquid alignment film

12‧‧‧ITO (Indium Tin Oxide) evaporation substrate

Fig. 1 is a view schematically showing an example of an anisotropic introduction treatment in a method for producing a liquid crystal alignment film used in the present invention, in which a crosslinkable organic group is used for a photosensitive side chain, and the introduced anisotropy is small. Figure.

2 is a view schematically showing an example of an anisotropic introduction process in a method for producing a liquid crystal alignment film used in the present invention, in which a crosslinkable organic group is used for a photosensitive side chain, and when the introduced anisotropy is large Picture.

Fig. 3 is a view schematically showing an example of an anisotropic introduction treatment in a method for producing a liquid crystal alignment film used in the present invention, which is based on the use of an organic group which causes light Fres rearrangement or isomerization in a photosensitive side chain. Imported anisotropy The picture of the hour.

Fig. 4 is a view schematically showing an example of the anisotropic introduction treatment in the method for producing a liquid crystal alignment film used in the present invention, which is based on the use of an organic group which causes light Fres rearrangement or isomerization in a photosensitive side chain. , the map of the imported anisotropy is large.

Fig. 5 is a view showing an example of a coating film image of an optical microscope used for evaluating the linearity of the end portion of the liquid crystal alignment film.

Fig. 6 is a view showing an example of a coating film image of an optical microscope used for evaluating the bulging of the end portion of the liquid crystal alignment film.

[Best Mode for Carrying Out the Invention]

The results of active research by the team of the present invention obtained the following findings and thus completed the present invention.

The polymer composition used in the production method of the present invention has a photosensitive side chain type polymer (hereinafter also referred to as a side chain type polymer) which exhibits liquid crystallinity, and the coating film obtained by using the above polymer composition has A film of a photosensitive side chain type polymer exhibiting liquid crystallinity. The coating film was subjected to alignment treatment without being subjected to rubbing treatment by polarized light irradiation. In addition, after the polarized light irradiation, the step of heating the side chain type polymer film is carried out, and a coating film to which the alignment control energy is imparted (hereinafter also referred to as a liquid crystal alignment film) is obtained. At this time, the anisotropy exhibited by only the polarized light irradiation becomes the driving force, and the liquid-chain side chain type polymer itself is effectively realigned by self-organization. As a result, high-efficiency alignment processing as a liquid crystal alignment film can be realized, and high alignment control can be obtained. Liquid crystal alignment film.

Further, in the polymer composition of the present invention, in addition to the side chain type polymer of the component (A) and the organic solvent of the component (C), diisobutylmethanol is used as the component (B).

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

<Method for Producing Substrate Having Liquid Crystal Alignment Film> and <Method for Manufacturing Liquid Crystal Display Element>

The method for producing a substrate having a liquid crystal alignment film of the present invention has the following steps: [I] a step of applying a polymer composition containing the following components onto a substrate having a conductive film for driving a transverse electric field to form a coating film, (A) a photosensitive side chain type polymer exhibiting liquid crystallinity in a specific temperature range, (B) diisobutylmethanol, and (C) an organic solvent; [II] irradiation of a coating film obtained in [I] a step of polarizing ultraviolet rays; and [III] a step of heating the coating film obtained in [II].

According to the above steps, a liquid crystal alignment film for a lateral electric field drive type liquid crystal display device to which an alignment control energy is imparted can be obtained, and a substrate having the liquid crystal alignment film can be obtained.

Moreover, in addition to the substrate (first substrate) obtained above, A lateral electric field drive type liquid crystal display element can be obtained by preparing the second substrate.

The second substrate is driven by using the substrate having the conductive film for driving the lateral electric field instead of the substrate having the conductive film for driving the transverse electric field, by using the above steps [I] to [III] (due to the use without the transverse electric field drive) The substrate of the conductive film is used, and for the sake of convenience, sometimes referred to as the steps [I'] to [III'] in the present application, the second substrate having the liquid crystal alignment film to which the alignment control energy is imparted can be obtained. .

The method for producing a lateral electric field drive type liquid crystal display device has the following step [IV]: [IV] the first and second substrate pairs obtained as described above are such that the liquid crystal alignment films of the first and second substrates are opposed to each other via a liquid crystal The step of obtaining a liquid crystal display element in a configuration. Thereby, a lateral electric field drive type liquid crystal display element can be obtained.

Hereinafter, each step of [I] to [III] and [IV] of the production method of the present invention will be described.

<Step [I]>

In the step [I], a polymer composition containing a photosensitive side chain type polymer exhibiting liquid crystallinity in a specific temperature range, diisobutylmethanol, and an organic solvent is applied to a conductive film having a lateral electric field drive. On the substrate, a coating film is formed.

<Substrate>

The substrate is not particularly limited, but the liquid crystal display element produced is In the case of a transmission type, it is preferred to use a substrate having high transparency. In this case, there is no particular limitation, and a glass substrate, a plastic substrate such as an acrylic substrate or a polycarbonate substrate, or the like can be used.

Further, in consideration of the application of the reflective liquid crystal display element, an opaque substrate such as a germanium wafer can also be used.

<Conductive film for driving a transverse electric field>

The substrate is a conductive film having a lateral electric field drive.

In the case where the liquid crystal display device is of a transmissive type, the conductive film may be, for example, ITO (Indium Tin Oxide) or IZO (Indium Zinc Oxide), but is not limited thereto.

In the case of the reflective liquid crystal display device, a material such as aluminum which can reflect light can be used as the conductive film, but the material is not limited thereto.

A method of forming a conductive film on a substrate can be carried out by a conventional method.

<Polymer composition>

The polymer composition is coated on a substrate having a conductive film for driving a transverse electric field, particularly on a conductive film.

The polymer composition used in the production method of the present invention contains (A) a photosensitive side chain type polymer exhibiting liquid crystallinity in a specific temperature range, (B) diisobutylmethanol, and (C) Organic solvents.

<<(A) Side chain type polymer>>

(A) component is a photosensitive film exhibiting liquid crystallinity in a specific temperature range Side chain type polymer.

(A) The side chain type polymer may be a liquid crystal having a wavelength range of from 250 nm to 400 nm and exhibiting liquid crystallinity in a temperature range of from 100 ° C to 300 ° C.

The (A) side chain type polymer preferably has a photosensitive side chain which reacts with light in a wavelength range of from 250 nm to 400 nm.

The (A) side chain type polymer preferably has a mesogenic group for exhibiting liquid crystallinity in a temperature range of 100 ° C to 300 ° C.

(A) The side chain type polymer has a photosensitive side chain bonded to the main chain, and may cause a crosslinking reaction, an isomerization reaction, or a light Fres rearrangement by light induction. The structure of the photosensitive side chain is not particularly limited, but is preferably a structure which causes a crosslinking reaction or a light-floating rearrangement for light induction, and more preferably causes a crosslinking reaction. In this case, even if it is exposed to external stress such as heat, the achieved alignment control energy can be stably maintained for a long period of time. The structure of the photosensitive side chain type polymer which exhibits liquid crystallinity is not particularly limited as long as it satisfies the characteristics, but it is preferable to have a rigid mesogen component in the side chain structure. In this case, when the side chain type polymer is used as the liquid crystal alignment film, stable liquid crystal alignment can be obtained.

The structure of the polymer may be, for example, a main chain and a side chain bonded thereto, and the side chain has a mesogen such as a biphenyl group, a terphenyl group, a phenylcyclohexyl group, a phenyl benzoate group or an azobenzene group. a component having a photosensitive group bonded to a light-inducing reaction at the front end portion for crosslinking reaction or isomerization reaction, or a main chain and a side chain bonded thereto, and the side chain having a mesogenic composition And can carry out the structure of the phenyl benzoate group of the light Fres rearrangement reaction Made.

More specific examples of the structure of the side chain type polymer capable of exhibiting liquid crystallinity are preferably selected from the group consisting of hydrocarbons, (meth) acrylates, itaconates, fumarates, At least one of a group consisting of a radical polymerizable group such as maleic acid ester, α -methylene- γ -butyrolactone, styrene, vinyl, maleimide, norbornene, and a group of siloxanes The main chain and the structure of the side chain composed of at least one of the following formulas (1) to (6).

Wherein A, B and D each independently represent a single bond, -O-, -CH ₂ -, -COO-, -OCO-, -CONH-, -NH-CO-, -CH=CH-CO-O- Or -O-CO-CH=CH-; S is an alkylene group having 1 to 12 carbon atoms, and the hydrogen atom bonded to the hydrogen atom may be substituted with a halogen group; T is a single bond or a carbon number of 1 to 12 An alkyl group, and a hydrogen atom bonded to the hydrogen atom may be substituted with a halogen group; Y ₁ represents a benzene ring selected from a monovalent group, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring, and a carbon number of 5-8 The ring of the alicyclic hydrocarbon or the group of the same or different 2 to 6 ring systems selected from the substituents bonded through the bonding group B, and the hydrogen atoms bonded to the hydrogen atoms may be 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, carbon The alkyl group having 1 to 5 or the alkyl group having 1 to 5 carbon atoms is substituted; the Y ₂ is selected from the group consisting of a divalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring, and a carbon number of 5~ a group of 8 alicyclic hydrocarbons, and a combination of such groups, the hydrogen atoms bonded to the hydrogen atoms may be independently independently -NO ₂ , -CN, -CH=C(CN) ₂ , -CH= CH-CN, halogen group, alkyl group having 1 to 5 carbon atoms, or carbon number 1 Substituted with an alkyloxy group of ~5; R represents a hydroxyl group, an alkoxy group having 1 to 6 carbon atoms, or represents the same definition as Y ₁ ; X represents a single bond, -COO-, -OCO-, -N=N -, -CH=CH-, -C≡C-, -CH=CH-CO-O-, or -O-CO-CH=CH-, X may be the same or different when X is 2; Cou Representing a coumarin-6-yl or coumarin-7-yl group, and the hydrogen atoms bonded to the hydrogen atoms may be independently independently -NO ₂ , -CN, -CH=C(CN) ₂ , -CH=CH -CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or an alkyloxy group having 1 to 5 carbon atoms; one of q1 and q2 is 1 and the other is 0; q3 is 0 or 1; P and Q are each independently 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 a combination thereof. However, when X is -CH=CH-CO-O- and -O-CO-CH=CH-, P or Q on the side of the bond of -CH=CH- is an aromatic ring, and when the number of P is 2 or more P may be the same or different from each other. When the number of Q is 2 or more, Q may be the same or different; 11 is 0 or 1; 12 is an integer of 0 to 2; when both 11 and 12 are 0, T is a single A also indicates a single bond when the key is; when 11 is 1, B is also a single bond when T is a single bond; H and I are independent Is selected from the bivalent benzene, naphthalene, biphenyl ring, a furan ring, a pyrrole ring, and the group of combinations of these.

The side chain is preferably one selected from the group consisting of the following formulas (7) to (10).

In the formula, A, B, D, Y ₁ , X, Y ₂ , and R have the same definitions as above; l represents an integer from 1 to 12; m represents an integer from 0 to 2, and m1 and m2 represent 1 to 3; Integer; n represents an integer from 0 to 12 (but B is a single bond when n=0).

The side chain is preferably one selected from the group consisting of the following formulas (11) to (13).

Where A, X, l, m, m2 and R have the same set as above Righteousness.

The side chain is preferably a photosensitive side chain represented by the following formula (14) or (15).

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

The side chain is preferably a photosensitive side chain represented by the following formula (16) or (17).

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

Further, the side chain is preferably a photosensitive side chain represented by the following formula (18) or (19).

In the formula, A, B, Y1, q1, q2, m1, and m2 have the same definitions as described 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 alkyl group having 1 to 5 carbon atoms. Oxygen.

The side chain is preferably a photosensitive side chain represented by the following formula (20).

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

Further, the (A) side chain type polymer preferably has any one of liquid crystal side chains selected from the group consisting of the following formulas (21) to (31).

In the formula, A, B, q1 and q2 have the same definitions as above; Y ₃ is selected from the group consisting of a monovalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a nitrogen-containing hetero ring and a carbon number 5-8. a group of a cyclic hydrocarbon, and a combination of the above, the hydrogen atom bonded to the hydrogen atom may be independently -NO ₂ , -CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or a carbon number Substituted by an alkyl group of 1 to 5; R ₃ represents a hydrogen atom, -NO ₂ , -CN, -CH=C(CN) ₂ , -CH=CH-CN, a halogen group, a monovalent benzene ring, naphthalene a ring, a biphenyl ring, a furan ring, a nitrogen-containing hetero ring, an alicyclic hydrocarbon having 5 to 8 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms; and 1 represents 1 to 12 In the integer, m represents an integer from 0 to 2, but in the formulas (25) to (26), the total of all m is 2 or more, and in the formulas (27) to (28), the total of all m is 1 or more, and m1. M2 and m3 each independently represent an integer of 1 to 3; R ₂ represents 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 hetero ring, and An alicyclic hydrocarbon having 5 to 8 carbon atoms; and an alkyl group or an alkyloxy group; Z ₁ and Z ₂ represent a single bond, -CO-, -CH ₂ O-, -CH=N-, -CF ₂ -.

<<Method for producing photosensitive side chain type polymer>>

The photosensitive side chain type polymer which exhibits liquid crystallinity can be obtained by polymerizing the photoreactive side chain monomer having a photosensitive side chain and a liquid crystal side chain monomer.

[Photoreactive side chain monomer]

The "photoreactive side chain monomer" refers to a monomer which can form a polymer having a photosensitive side chain at a side chain portion of a polymer when a polymer is formed.

As the photoreactive group having a side chain, the following structure and its derivative are preferred biological.

More specific examples of the photoreactive side chain monomer preferably have a hydrocarbon selected from the group consisting of a hydrocarbon, a (meth) acrylate, an itaconate, a fumarate, a maleate, and an α -methylene group. a polymerizable group composed of at least one of a radical polymerizable group such as γ -butyrolactone, styrene, vinyl group, maleic imine or norbornene, and a group consisting of a siloxane, and the above formula The structure of the photosensitive side chain composed of at least one of (1) to (6) is preferably a photosensitive side chain composed of at least one of the above formulas (7) to (10), and is represented by the above formula ( a photosensitive side chain composed of at least one of 11) to (13), a photosensitive side chain represented by the above formula (14) or (15), and a photosensitive side represented by the above formula (16) or (17) The chain, the photosensitive side chain represented by the above formula (18) or (19), and the photosensitive side chain represented by the above formula (20).

The present application provides novel compounds (1) to (11) represented by the following formulas (1) to (11) and compounds (12) to (17) represented by the following formulas (12) to (17). Photoreactive and/or liquid crystal side chain monomer.

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

[Liquid Crystal Side Chain Monomer]

The term "liquid crystal side chain monomer" means that the polymer derived from the monomer exhibits liquid crystallinity, and the polymer is a monomer capable of forming a mesogenic group at a side chain portion.

As a mesogenic group having a side chain, it may be a biphenyl group or a benzoic acid benzene. The ester or the like may be a group of a mesogenic structure alone, or may be a group having a mesogenic structure by hydrogen bonding the side chains such as benzoic acid. The mesogen group which the side chain has is preferably the following structure.

More specifically, as the liquid crystal side chain monomer, it is preferably selected from the group consisting of hydrocarbons, (meth) acrylates, itaconates, fumarates, maleates, α-methylene-γ- a polymerizable group composed of at least one of a radical polymerizable group such as butyrolactone, styrene, vinyl, maleimide, norbornene, and a group consisting of a siloxane, and the above formula (21) The structure of the side chain formed by at least one of ~(31).

The (A) side chain type polymer can be obtained by the polymerization reaction of the above-mentioned photoreactive side chain monomer exhibiting liquid crystallinity. Further, copolymerization of a photoreactive side chain monomer having no liquid crystallinity and a liquid crystal side chain monomer, or copolymerization of a photoreactive side chain monomer exhibiting liquid crystallinity and a liquid crystal side chain monomer can be achieved. Come and get. Further, it can be copolymerized with other monomers without impairing the performance of liquid crystallinity.

As the other monomer, for example, a monomer which can be obtained by radical polymerization in the industry can be cited.

Specific examples of the other monomer include an unsaturated carboxylic acid, an acrylate compound, a methacrylate compound, a maleimide compound, acrylonitrile, maleic anhydride, a styrene compound, and a vinyl compound.

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

Examples of the acrylate compound include methyl acrylate, ethyl acrylate, isopropyl acrylate, benzyl acrylate, naphthyl acrylate, decyl acrylate, decyl methyl acrylate, phenyl acrylate, and acrylic acid 2, 2, 2. -trifluoroethyl ester, tributyl acrylate, cyclohexyl acrylate, isobornyl acrylate, 2-methoxyethyl acrylate, methoxy triethylene glycol acrylate, 2-ethoxyethyl acrylate, Tetrahydrofurfuryl acrylate, 3-methoxybutyl acrylate, 2-methyl-2-adamantyl acrylate, 2-propyl-2-adamantyl acrylate, 8-methyl-8-tricyclopropene acrylate Ester and 8-ethyl-8-tricyclodecyl acrylate.

Examples of the methacrylate compound include methyl methacrylate, ethyl methacrylate, isopropyl methacrylate, benzyl methacrylate, naphthyl methacrylate, decyl methacrylate, and methyl group. Mercaptomethyl acrylate, phenyl methacrylate, 2,2,2-trifluoroethyl methacrylate, tert-butyl methacrylate, cyclohexyl methacrylate, isobornyl methacrylate, methyl 2-methoxyethyl acrylate, methoxytriethylene glycol methacrylate, 2-ethoxyethyl methacrylate, tetrahydrofurfuryl methacrylate, 3-methoxybutyl methacrylate 2-methacrylic acid 2- Base-2-adamantyl ester, 2-propyl-2-adamantyl methacrylate, 8-methyl-8-tricyclodecyl methacrylate, and 8-ethyl-8-tricyclomethacrylate Ester ester and the like. Glycidyl (meth)acrylate, (3-methyl-3-oxetanyl)methyl (meth)acrylate, and (meth)acrylic acid (3-ethyl-3-oxocyclo) can also be used. A (meth) acrylate compound having a cyclic ether group such as butyl)methyl ester.

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.

Examples of the styrene compound include styrene, methyl styrene, chlorostyrene, and bromostyrene.

Examples of the maleinimide compound include maleimide, N-methylmaleimide, N-phenylmaleimide, and N-cyclohexylmaleimide.

The method for producing the side chain type polymer of the present embodiment is not particularly limited, and a widely used method which is industrially processed can be used. Specifically, it can be produced by cationic polymerization, radical polymerization, or anionic polymerization using a liquid crystal side chain monomer or a vinyl group of a photoreactive side chain monomer. Among these, radical polymerization is optimal because of the ease of reaction control and the like.

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

Free radical thermal polymerization initiator by heating to decomposition temperature The above compounds which generate free radicals. Examples of the radical thermal polymerization initiator include ketone peroxides (methyl ethyl ketone peroxide, cyclohexanone peroxide, etc.) and dimercapto peroxides (ethyl hydrazide). Oxide, benzamidine peroxide, etc.), hydrogen peroxide (hydrogen peroxide, tert-butyl hydroperoxide, cumene hydroperoxide, etc.), dialkyl hydrogen peroxide (di- Tributyl peroxide, dicumyl peroxide, dilauroyl peroxide, etc.), peroxyketals (dibutylperoxycyclohexane, etc.), alkyl peresters ( Peroxy neodecanoic acid tert-butyl ester, peroxypivalic acid tert-butyl ester, peroxy 2-ethylcyclohexanoic acid third amyl ester, etc.), persulfate (potassium persulfate, persulfate) Sodium, ammonium persulfate, etc.), azo compounds (azobisisobutyrine, and 2,2'-bis(2-hydroxyethyl)azobisisobutyrine). These radical thermal polymerization initiators may be used alone or in combination of two or more.

The radical photopolymerization initiator is not particularly limited as long as it is a compound which starts radical polymerization by irradiation with light. Examples of the radical photopolymerization initiator include benzophenone, Michael's ketone, 4,4'-bis(diethylamino)benzophenone, xanthone, and thioxanthone. , Isopropyl xanthone, 2,4-diethylthioxanthone, 2-ethylhydrazine, acetophenone, 2-hydroxy-2-methylpropiophenone, 2-hydroxy-2-methyl- 4'-isopropylpropiophenone, 1-hydroxycyclohexyl phenyl ketone, isopropyl benzoine ether, isobutyl benzoin ether, 2,2-diethoxyacetophenone, 2,2- Dimethoxy-2-phenylacetophenone, camphorquinone, benzanthrone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinylpropane- 1-ketone, 2-benzyl-2-dimethylamino-1-(4-morpholinylphenyl)-butanone-1, ethyl 4-dimethylaminobenzoate, 4-dimethylamino Isoamyl benzoate, 4,4'-bis(t-butylperoxycarbonyl)benzophenone, 3,4,4'-tris(t-butylperoxycarbonyl)benzophenone, 2,4,6-trimethylbenzimidyldiphenylphosphine oxide, 2-(4'-methoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(3',4'-dimethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(2',4'-dimethoxystyrene -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-bis(ethoxycarbonylmethyl)] -2,6-bis(trichloromethyl)-s-triazine, 1,3-bis(trichloromethyl)-5-(2'-chlorophenyl)-s-triazine, 1,3- Bis(trichloromethyl)-5-(4'-methoxyphenyl)-s-triazine, 2-(p-dimethylaminostyryl)benzoxazole, 2-(p-di) Methylaminostyryl)benzothiazole, 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'-indole (4-ethoxycarbonyl) Phenyl)-1,2'-biimidazole, 2 , 2'-bis(2,4-dichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis(2,4-di Bromophenyl)-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-morpholinylpropanyl)-9-n-dodecylcarbazole, 1-hydroxycyclohexyl phenyl ketone, bis(5-2,4-cyclopentadien-1-yl)-bis (2 ,6-difluoro-3-(1H-pyrrol-1-yl)-phenyl)titanium, 3,3',4,4'-tetrakis(t-butylperoxycarbonyl)benzophenone, 3 , 3',4,4'-tetra(trihexylperoxycarbonyl)benzophenone, 3,3'-bis(methoxycarbonyl)-4,4'-di(t-butylperoxy Benzocarbonyl)benzophenone, 3,4'-bis(methoxycarbonyl)-4,3'-bis(t-butylperoxycarbonyl)benzophenone, 4,4'-di(methoxy Carbonyl)-3,3'-bis(t-butylperoxycarbonyl)benzophenone, 2-(3-methyl-3H-benzothiazol-2-ylidene)-1-naphthalene-2- Ethyl-ketone or 2-(3-methyl-1,3-benzothiazol-2(3H)-ylidene)-1-(2-benzylidene)ethanone. These compounds may be used singly or in combination of two 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, or the like can be used.

The organic solvent used in the polymerization reaction of the photosensitive side chain type polymer which exhibits liquid crystallinity is not particularly limited as long as it can dissolve the produced polymer. Specific examples thereof are as follows.

N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, N-methylene Indamine, dimethyl hydrazine, tetramethyl urea, pyridine, dimethyl hydrazine, hexamethylarylene, γ-butyrolactone, isopropanol, methoxymethylpentanol, dipentene, B Kefenyl ketone, methyl decyl ketone, methyl ethyl ketone, methyl isoamyl ketone, methyl isopropyl ketone, methyl stilbene, ethyl serotonin, methyl sarbuta acetic acid Ester, ethyl sirolimus acetate, butyl carbitol, ethyl carbitol, 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 diethylene glycol 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, C Ether, dihexyl ether, dioxane, n-hexane, n-pentane, n-octane, diethyl ether, cyclohexanone, ethyl carbonate, propyl carbonate, methyl lactate, ethyl lactate, acetic acid Methyl ester, ethyl acetate, n-butyl acetate, propylene glycol monoethyl ether acetate, methyl pyruvate, ethyl pyruvate, methyl 3-methoxypropionate, methyl ethyl 3-ethoxypropionate , 3-methoxypropionic acid ethyl ester, 3-ethoxypropionic acid, 3-methoxypropionic acid, 3-methoxypropionic acid propyl ester, 3-methoxypropionic acid butyl ester, diethylene glycol Dimethyl ether, 4-hydroxy-4-methyl-2-pentanone, 3-methoxy-N,N-dimethylpropane decylamine, 3-ethoxy-N,N-dimethylpropane oxime Amine, 3-butoxy-N,N-dimethylpropane decylamine, and the like.

These organic solvents may be used singly or in combination. Further, even a solvent which does not dissolve the produced polymer may be used in the organic solvent in a range in which the formed polymer is not precipitated.

Further, since oxygen in the organic solvent in the radical polymerization is a cause of hindering the polymerization reaction, it is preferred to use a degassing to an organic solvent.

The polymerization temperature in the radical polymerization may be any temperature of from 30 ° C to 150 ° C, but is preferably in the range of from 50 ° C to 100 ° C. Further, the reaction can be carried out at any concentration, but when the concentration is too low, it is difficult to obtain a polymer having a high molecular weight. When the concentration is too high, the viscosity of the reaction liquid becomes too high and it is difficult to uniformly stir, so the monomer concentration is preferably 1 mass. %~50% by mass, more preferably 5 Mass%~30% by mass. The initial stage of the reaction is carried out at a high concentration, and then an organic solvent can be added.

In the above-mentioned radical polymerization reaction, when the ratio of the radical polymerization initiator is larger than that of the monomer, the molecular weight of the obtained polymer becomes small, and when the amount of the polymer is small, the molecular weight of the polymer becomes large, so the radical initiator The ratio is preferably from 0.1 mol% to 10 mol% with respect to the monomer to be polymerized. Further, various monomer components, solvents, initiators, and the like may be added during the polymerization.

[Recovery of Polymers]

When the polymer produced by recovering the reaction solution of the photosensitive side chain type polymer which exhibits liquid crystallinity obtained by the above reaction is used, it is only necessary to introduce the reaction solution into a weak solvent to precipitate the polymer. Examples of the weak solvent used for the precipitation include methanol, acetone, hexane, heptane, butyl cellosolve, heptane, methyl ethyl ketone, methyl isobutyl ketone, ethanol, toluene, benzene, diethyl ether. , methyl ethyl ether, water, and the like. The polymer precipitated in the weak solvent is recovered by filtration, and then dried at normal temperature or under reduced pressure under normal pressure or reduced pressure. Further, when the polymer recovered by precipitation is redissolved in an organic solvent and the operation of reprecipitation recovery is repeated two to ten times, impurities in the polymer can be reduced. Examples of the weak solvent in this case include alcohols, ketones, and hydrocarbons. When three or more kinds of weak solvents selected from the above are used, the purification efficiency can be further improved.

The molecular weight of the (A) side chain type polymer of the present invention, the weight of the obtained coating film, the workability at the time of formation of the coating film, and the uniformity of the coating film, the weight measured by GPC (gel permeation chromatography) method Average molecular weight The best is 2000~1000000, more preferably 5000~20000.

[Modulation of polymer composition]

The polymer composition used in the present invention is preferably prepared into a coating liquid in a manner suitable for formation of a liquid crystal alignment film. That is, the polymer composition used in the present invention is preferably prepared by dissolving a resin component for forming a resin film in an organic solvent. Here, the resin component is a resin component containing a photosensitive side chain type polymer which exhibits liquid crystallinity as described above. In this case, the content of the resin component is preferably from 1% by mass to 20% by mass, more preferably from 3% by mass to 15% by mass, most preferably from 3% by mass to 10% by mass.

In the polymer composition of the present embodiment, all of the resin components may be a side chain type polymer which exhibits liquid crystallinity, but may be mixed in a range which does not impair the liquid crystal display performance and photosensitivity. Other polymers than others. In this case, the content of the other polymer in the resin component is from 0.5% by mass to 80% by mass, preferably from 1% by mass to 50% by mass.

Examples of the other polymer include a polymer of a photosensitive side chain type polymer which does not exhibit liquid crystallinity, such as poly(meth)acrylate, polyglycolic acid or polyimine.

<<(B) component>>

The polymer composition used in the present invention contains, as the component (B), diisobutylmethanol represented by the following structural formula, that is, 2,6-dimethyl-4-heptanol.

When the liquid crystal alignment agent contains diisobutylmethanol, the liquid crystal alignment agent which does not contain it can suppress the wettability, and the linearity of the end portion which becomes a liquid crystal alignment film becomes high. Moreover, the bulging of the end portion can be suppressed. This is considered to be due to the boiling point/vapor pressure of diisobutylmethanol, compared to the weak solvent of butyl sirolimus or propylene glycol monobutyl ether, which can be drawn closer to the good solvent N-methyl The solvent of the vapor pressure curve of 2-pyrrolidone (NMP) or N-ethyl-2-pyrrolidone (NEP), or evaporation by a weak solvent, thereby suppressing the bulging of the end.

The content of the component (B) is preferably 20 to 60 parts by mass, more preferably 25 to 45 parts by mass, per 100 parts by mass of the organic solvent of the component (C).

<<(C) Organic Solvents>>

The organic solvent used in the polymer composition used in the present invention is not particularly limited as long as it can dissolve the resin component. Specific examples thereof are listed below.

N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylcaprolactam, 2-pyrrolidone, N- Ethyl pyrrolidone, N-vinylpyrrolidone, dimethyl hydrazine, tetramethyl urea, pyridine, dimethyl hydrazine, hexamethylarylene, γ-butyrolactone, 3-methoxy- N,N-dimethylpropanamide, 3-ethoxy-N,N-dimethylpropanamide, 3-butoxy-N,N-dimethylpropanamide, 1,3-two Methyl-imidazolidinone, ethyl amyl ketone, methyl hydrazine Ketone, methyl ethyl ketone, methyl isoamyl ketone, methyl isopropyl ketone, cyclohexanone, ethyl carbonate, propyl 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, diethyl 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, and the like. These may be used singly or in combination. These may be used alone or in combination.

The polymer composition used in the present invention may contain components other than the above components (A), (B) and (C). Examples thereof include a solvent or a compound which improves uniformity of film thickness or surface smoothness when a polymer composition is applied, a compound which improves adhesion between a liquid crystal alignment film and a substrate, and the like, but are not limited thereto.

Specific examples of the solvent (weak solvent) for improving the uniformity of the film thickness or the surface smoothness include the following.

For example, isopropanol, methoxymethylpentanol, methyl stilbene, ethyl sirlox, butyl siroli, methyl sarbuta acetate, ethyl sarbuta 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, methyl 3-methoxypropionate, 3- Methyl ethyl ethoxypropionate, ethyl 3-methoxypropionate, 3-ethoxypropionic acid, 3-methoxypropionic acid, propyl 3-methoxypropionate, 3-methoxy Butyl propyl 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-monoethyl ether -2-acetate, dipropylene glycol, 2-(2-ethoxypropoxy)propanol, methyl lactate, ethyl lactate, n-propyl lactate, n-butyl lactate, isoamyl lactate, etc. have low Organic solvent for surface tension, etc.

These weak solvents may be used alone or in combination of plural kinds. When the solvent is used as described above, it is preferably 5% by mass to 80% by mass, more preferably 20% by mass to 60% by mass of the solvent as a whole, so that the solubility of the solvent contained in the polymer composition is not significantly lowered. quality%.

Examples of the compound for improving the uniformity of the film thickness or the surface smoothness include a fluorine-based surfactant, a polyfluorene-based surfactant, and a nonionic surfactant.

More specifically, for example, EF TOP (registered trademark) EF301, EF303, EF352 (manufactured by TOKEMU PRODUCTS), MEGAFAC (registered trademark) F171, F173, R-30 (manufactured by DIC Corporation), FLORARD FC430, FC431 (manufactured by Sumitomo 3M Co., Ltd.) ASAHI GUARD (registered trademark) AG710 (manufactured by Asahi Glass Co., Ltd.), SURFLON (registered trademark) S-382, SC101, SC102, SC103, SC104, SC105, SC106 (manufactured by AGC Seimi Chemical Co., Ltd.). The use ratio of the surfactant is preferably 0.01 parts by mass to 2 parts by mass, more preferably 0.01 parts by mass to 1 part by mass, per 100 parts by mass of the resin component contained in the polymer composition.

Specific examples of the compound which improves the adhesion between the liquid crystal alignment film and the substrate include a compound containing a functional decane as shown below.

For example, 3-aminopropyltrimethoxydecane, 3-aminopropyltriethoxydecane, 2-aminopropyltrimethoxydecane, 2-aminopropyltriethoxydecane, N-(2-Aminoethyl)-3-aminopropyltrimethoxydecane, N-(2-aminoethyl)-3-aminopropylmethyldimethoxydecane, 3-urea Propyltrimethoxydecane, 3-ureidopropyltriethoxydecane, N-ethoxycarbonyl-3-aminopropyltrimethoxydecane, N-ethoxycarbonyl-3-aminopropyl Triethoxy decane, N-triethoxydecylpropyltriethylamine, N-trimethoxydecylpropyltriethylamine, 10-trimethoxydecyl-1 4,7-triazadecane, 10-triethoxydecyl-1,4,7-triazadecane, 9-trimethoxydecyl-3,6-diazadecyl acetate , 9-triethoxydecyl acetate-3,6-diazadecyl ester, N-benzyl-3-aminopropyl Trimethoxy decane, N-benzyl-3-aminopropyltriethoxy decane, N-phenyl-3-aminopropyltrimethoxydecane, N-phenyl-3-aminopropyl Triethoxy decane, N-bis(oxyethylidene)-3-aminopropyltrimethoxydecane, N-bis(oxyethylidene)-3-aminopropyltriethoxydecane, and the like.

In addition to the adhesion between the substrate and the liquid crystal alignment film, the phenoplast may be contained in the polymer composition for the purpose of preventing deterioration of electrical characteristics due to the backlight when the liquid crystal display element is formed. An additive to a compound containing an epoxy group. Specific phenolic plastic additives are shown below, but are not limited to this configuration.

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, and polypropylene glycol diglycidyl ether. , neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, glycerol diglycidyl ether, 2,2-dibromoneopentyl glycol diglycidyl ether, 1,3,5 ,6-tetraglycidyl-2,4-hexanediol, N,N,N',N'-tetraglycidyl-m-xylylenediamine, 1,3-bis(N,N-bi-dihydrate) Glycerylaminomethyl)cyclohexane, N,N,N',N'-tetraglycidyl-4,4'-diaminodiphenylmethane, and the like.

When a compound which improves the adhesion to the substrate is used, the amount thereof is preferably 0.1 parts by mass to 30 parts by mass, more preferably 1 part by mass to 20 parts by mass per 100 parts by mass of the resin component contained in the polymer composition. Parts by mass. When the amount used is less than 0.1 part by mass, the adhesion improving effect cannot be expected, and when it is more than 30 parts by mass, the alignment of the liquid crystal may be deteriorated.

A photosensitizer can also be used as an additive. Preferred are colorless sensitizers and triplet sensitizers.

As the photosensitizer, for example, an aromatic nitro compound, coumarin (7-diethylamino-4-methylcoumarin, 7-hydroxy-4-methylcoumarin), ketone Bean, carbonyl dicoumarin, aromatic 2-hydroxy ketone, and amine-substituted aromatic 2-hydroxy ketone (2-hydroxybenzophenone, mono or di-p-(dimethylamino) -2-hydroxybenzophenone), acetophenone, anthracene, xanthone, thioxanthone, benzoxanone, thiazoline (2-benzylidenemethylene-3-methyl-β- Naphthacylthiazoline, 2-(β-naphthylmethylene)-3-methylbenzothiazoline, 2-(α-naphthylmethylene)-3-methylbenzothiazoline, 2-( 4-biphenolylmethylene)-3-methylbenzothiazoline, 2-(β-naphthylmethylidene)-3-methyl-β-naphthylthiazoline, 2-(4-biphenol Methylmethyl)-3-methyl-β-naphthylthiazoline, 2-(p-fluorobenzhydrylmethylene)-3-methyl-β-naphthylthiazoline), oxazoline 2-benzylidene methylene-3-methyl-β-naphthyloxazoline, 2-(β-naphthylmethylene)-3-methylbenzoxazoline, 2-(α- Naphthylmethylidene methylene)-3-methylbenzoxazoline, 2-(4-biphenolol methylene)-3-methylbenzoxazoline, 2-(β-naphthoquinone Benzylmethyl)-3-methyl-β-naphthyloxazoline, 2-(4-bisphenol benzylidene)-3-methyl-β-naphthyloxazoline, 2-(p- Fluorobenzhydrylmethylene)-3-methyl-β-naphthoxazole Porphyrin), benzothiazole, nitroaniline (m- or p-nitroaniline, 2,4,6-trinitroaniline) or nitroguanidine (5-nitroguanidine), (2-[( m-Hydroxy-p-methoxy)styryl]benzothiazole, benzhydryl alkyl ether, N-alkyl phthalone, acetophenone ketal (2,2-dimethoxy) Phenyl phenyl ketone), naphthalene, anthracene (2-naphthylmethanol, 2-naphthalene carboxylic acid, 9-fluorene carbamide and 9-fluorene carboxylic acid), benzopyran, azo acridine, furocoumarin ( Furocoumarin) and so on.

Preferred are aromatic 2-hydroxyketone (benzophenone), coumarin, ketocoumarin, carbonyl dicoumarin, acetophenone, anthraquinone, xanthone, thioxanthone and acetophenone. ketone.

In addition to the above, the polymer composition may be added with a dielectric or a conductive material for the purpose of changing the dielectric properties of the liquid crystal alignment film or the electrical properties of the conductive layer, as long as the effect of the present invention is not impaired. A crosslinkable compound may be added for the purpose of improving the hardness or density of the film when the liquid crystal alignment film is formed.

The method of applying the above polymer composition to a substrate having a conductive film for driving a transverse electric field is not particularly limited.

The coating method is generally carried out in the industry by screen printing, lithography, flexographic printing or ink jet printing. Other coating methods include a dipping method, a roll coating method, a slit coating method, a spin coating method (spin coating method), a spray coating method, and the like, and these may be used depending on the purpose.

After the polymer composition is applied onto a substrate having a conductive film for driving a transverse electric field, it can be heated at 50 to 200 ° C by a heating means such as a hot plate, a heat cycle type oven or an IR (infrared) type oven. The solvent was evaporated at 50 to 150 ° C to obtain a coating film. The drying temperature at this time is preferably lower than the liquid crystal phase exhibiting temperature of the side chain type polymer.

When the thickness of the coating film is too thick, the power consumption of the liquid crystal display element becomes unfavorable. When the thickness of the liquid crystal display element is too small, the reliability of the liquid crystal display element may be lowered. Therefore, it is preferably 5 nm to 300 nm, more preferably 10 nm to 150 nm.

Further, after the step [I], the step of cooling the substrate on which the coating film is formed to room temperature may be provided before the step [II].

<Step [II]>

In the step [II], the coating film obtained in the step [I] is irradiated with polarized ultraviolet rays. When the film surface of the coating film is irradiated with polarized ultraviolet rays, the substrate is irradiated with polarized ultraviolet rays through a polarizing plate from a certain direction. As the ultraviolet rays to be used, ultraviolet rays having a wavelength in the range of 100 nm to 400 nm can be used. It is preferred to select the most appropriate wavelength by a filter or the like depending on the type of the coating film to be used. Further, for example, ultraviolet rays having a wavelength in the range of 290 nm to 400 mm are selected so as to selectively induce a photocrosslinking reaction. As the ultraviolet rays, for example, light emitted from a high pressure mercury lamp can be used.

The amount of ultraviolet light that is polarized is related to the coating film used. The amount of irradiation is preferably a polarized ultraviolet ray having a maximum value (hereinafter referred to as ΔAmax) of the difference between the absorbance of the ultraviolet ray in the direction parallel to the polarization direction of the polarized ultraviolet ray and the ultraviolet ray absorbance in the vertical direction (hereinafter referred to as ΔAmax). The range of 1% to 70% is more preferably in the range of 1% to 50%.

<Step [III]>

The step [III] is a film which is heated by the polarized ultraviolet irradiation in the step [II]. By heating, an alignment control energy can be imparted to the coating film.

Heating means a heating means such as a hot plate, a heat cycle type oven or an IR (infrared) type oven. The heating temperature can be determined by considering the temperature at which the liquid crystal of the coating film to be used exhibits liquid crystallinity.

The heating temperature is preferably within a temperature range in which the side chain type polymer exhibits liquid crystallinity (hereinafter referred to as liquid crystal display temperature). In the case of a film-like film surface, the liquid crystal display temperature of the surface of the coating film is estimated to be lower than the liquid crystal display temperature when the photosensitive side chain type polymer which exhibits liquid crystallinity is observed as a whole. Therefore, the heating temperature is more preferably in the temperature range in which the liquid crystal on the surface of the coating film exhibits temperature. That is, the temperature range of the heating temperature after the polarized ultraviolet irradiation is preferably such that the temperature lower than the lower limit of the temperature range of the liquid crystal display temperature of the side chain type polymer used is set to the lower limit, and is lower than the upper limit of the liquid crystal temperature range. The temperature at 10 ° C is set to the temperature in the range of the upper limit. When the heating temperature is lower than the above temperature range, the effect of the anisotropy increase by heat in the coating film tends to be insufficient, and when the heating temperature is too higher than the above temperature range, the state of the coating film approaches the direction. The tendency of the liquid state (isotropic phase), in which case it is difficult to re-align itself in one direction by self-organization.

Further, the liquid crystal display temperature refers to a glass transition temperature (Tg) or more when the surface of the side chain type polymer or the coating film is transferred from the solid phase to the liquid phase, and the phase transition from the liquid crystal phase to the isotropic phase ( The isotropic phase transfers the temperature below the in-phase temperature (Tiso).

By having the above steps, the production method of the present invention can efficiently realize the introduction of the anisotropy of the coating film. Moreover, the substrate with the liquid crystal alignment film can be efficiently manufactured.

<Step [IV]>

[IV] The step is to obtain the substrate (first substrate) having the liquid crystal alignment film on the conductive film for driving the transverse electric field in [III], and the same as that obtained in the above [I'] to [III']. A substrate (second substrate) having a liquid crystal alignment film having a conductive film is disposed so as to face each other with a liquid crystal alignment film interposed therebetween via a liquid crystal, and a liquid crystal cell is produced by a conventional method to produce a lateral electric field-driven liquid crystal. The steps to display the component. Further, the steps [I'] to [III'] are in addition to the step [I], except that the substrate having the conductive film for driving the transverse electric field is used instead of the substrate having the conductive film for driving the transverse electric field, and the step [ I]~[III] are also carried out. The difference between the steps [I] to [III] and the steps [I'] to [III'] is due to the presence or absence of only the above-mentioned conductive film, and the description of the steps [I'] to [III'] is omitted.

When the liquid crystal cell or the liquid crystal display device is produced as an example, the first and second substrates are prepared, and a spacer is dispersed on the liquid crystal alignment film of one of the substrates so that the liquid crystal alignment film surface is inside. The method of bonding the other substrate, injecting the liquid crystal under reduced pressure, and sealing, or adding the liquid crystal to the liquid crystal alignment film surface on which the spacer is dispersed, bonding the substrate, and sealing the same. At this time, it is preferable to use a substrate having an electrode such as a comb-tooth structure for driving a lateral electric field on the substrate on one side. The separator diameter at this time is preferably from 1 μm to 30 μm, more preferably from 2 μm to 10 μm. The spacer The diameter will determine the distance between one of the liquid crystal layers and the substrate, that is, the thickness of the liquid crystal layer.

In the method for producing a coated film substrate of the present invention, a polymer composition is applied onto a substrate to form a coating film, and then the polarized ultraviolet rays are irradiated. Then, the substrate is introduced into the liquid crystal alignment film having the alignment control energy of the liquid crystal by efficiently introducing the anisotropic property to the side chain type polymer film by heating.

The coating film used in the present invention utilizes the principle of molecular reorientation induced by self-organization of liquid crystallinity based on photoreaction of a side chain, thereby realizing the introduction of high-efficiency anisotropy of a coating film. In the method of the present invention, when the side chain type polymer has a photocrosslinkable group as a photoreactive group, the side chain type polymer is used to form a coating film on the substrate, and then the polarized ultraviolet ray is irradiated, followed by heating. After that, a liquid crystal display element is produced.

In the following, a form in which a side chain type polymer having a photocrosslinkable group as a photoreactive group is used is referred to as a first embodiment, and a group having a light Fress rearrangement group or causing isomerization is used. A form which is implemented as a side chain type polymer having a photoreactive group structure will be described as a second aspect.

1 is a view schematically showing an example of an anisotropic introduction process in a method for producing a liquid crystal alignment film of a side chain type polymer having a photocrosslinkable group as a photoreactive group in the first embodiment of the present invention. Figure. Fig. 1(a) is a view schematically showing a state of a side chain type polymer film before polarized light irradiation, and Fig. 1(b) is a view schematically showing a state of a side chain type polymer film after polarized light irradiation, Fig. 1 (c) ) is a schematic display of the heated In the case of the state of the side chain type polymer film, in particular, when the anisotropy of the introduction is small, that is, in the first aspect of the invention, the ultraviolet irradiation amount in the step [II] is such that the ΔA is at the maximum ultraviolet irradiation amount. Schematic diagram of the range from 1% to 15%.

FIG. 2 is a view showing an example of an anisotropic introduction process in a method for producing a liquid crystal alignment film of a side chain type polymer having a photocrosslinkable group as a photoreactive group in the first embodiment of the present invention. Picture. Fig. 2(a) is a view schematically showing a state of a side chain type polymer film before polarized light irradiation, and Fig. 2(b) is a view schematically showing a state of a side chain type polymer film after polarized light irradiation, and Fig. 2(c) The diagram schematically shows the state of the side chain type polymer film after heating, and in particular, the case where the introduction has a large anisotropy, that is, in the first aspect of the invention, the amount of ultraviolet irradiation in the step [II] is Δ. A is a schematic representation of the range of 15% to 70% of the maximum UV exposure.

3 is a side chain type schematically illustrating a structure in which a photoisomerization group having a photoisomerization group or a photorefractive group represented by the above formula (18) is used as a photoreactive group in the second embodiment of the present invention. A diagram showing an example of an anisotropic introduction process in a method for producing a polymer liquid crystal alignment film. Fig. 3(a) is a view schematically showing a state of a side chain type polymer film before polarized light irradiation, and Fig. 3(b) is a view schematically showing a state of a side chain type polymer film after polarized light irradiation, and Fig. 3(c) The diagram schematically shows the state of the side chain type polymer film after heating, and in particular, the case where the introduction has a small anisotropy, that is, in the second aspect of the invention, the amount of ultraviolet irradiation in the step [II] is Δ. A is a schematic diagram of the range of 1% to 70% of the maximum ultraviolet radiation.

FIG. 4 is a view schematically showing the manufacture of a liquid crystal alignment film of a side chain type polymer having a structure in which a photoreactive group represented by the above formula (19) is used as a photoreactive group in the second embodiment of the present invention. A diagram of an example of anisotropic import processing in a method. Fig. 4(a) is a view schematically showing a state of a side chain type polymer film before polarized light irradiation, and Fig. 4(b) is a view schematically showing a state of a side chain type polymer film after polarized light irradiation, and Fig. 4(c) The graph schematically shows the state of the side chain type polymer film after heating, and in particular, the degree of anisotropy of the introduction is large, that is, in the second aspect of the present invention, the amount of ultraviolet irradiation in the step [II] is Δ. A is a schematic diagram of the range of 1% to 70% of the maximum ultraviolet radiation.

In the first aspect of the present invention, in the anisotropic introduction process of the coating film, when the ultraviolet irradiation amount in the step [II] is in the range of 1% to 15% of the maximum ultraviolet irradiation amount, the ΔA is preceded by A coating film 1 is formed on the substrate. As shown in FIG. 1(a), the coating film 1 formed on the substrate has a structure in which the side chains 2 are randomly arranged. According to the random arrangement of the side chains 2 of the coating film 1, the mesogenic components and the photosensitive groups of the side chain 2 are also randomly aligned, and the coating film 1 is isotropic.

In the first aspect of the present invention, in the anisotropic introduction process of the coating film, when the ultraviolet irradiation amount in the step [II] is within the range of 15% to 70% of the maximum ultraviolet irradiation amount, the ΔA is preceded by A coating film 3 is formed on the substrate. As shown in FIG. 2(a), the coating film 3 formed on the substrate has a structure in which the side chains 4 are randomly arranged. According to the random arrangement of the side chains 4 of the coating film 3, the mesogenic components and the photosensitive groups of the side chains 4 are also randomly aligned, and the coating film 2 is isotropic.

In the second aspect of the present invention, a side chain using a structure having a photoisomerization group or a light-floating rearrangement group represented by the above formula (18) is used for the anisotropic introduction treatment of the coating film. In the case of the liquid crystal alignment film of the polymer, when the ultraviolet irradiation amount in the step [II] is in the range of 1% to 70% of the maximum ultraviolet irradiation amount, the coating film 5 is formed on the substrate. As shown in FIG. 3(a), the coating film 5 formed on the substrate has a structure in which the side chains 6 are randomly arranged. The mesogenic component and the photosensitive group of the side chain 6 are also randomly aligned according to the random arrangement of the side chains 6 of the coating film 5, and the side chain type polymer film 5 is isotropic.

In the second aspect of the present invention, when the liquid crystal alignment film of the side chain type polymer having the structure of the light-floating rearrangement group represented by the above formula (19) is used in the process of introducing the anisotropic film of the coating film When the ultraviolet irradiation amount of the step [II] is in the range of 1% to 70% of the maximum ultraviolet irradiation amount, the coating film 7 is formed on the substrate. As shown in FIG. 4(a), the coating film 7 formed on the substrate has a structure in which the side chains 8 are randomly arranged. Depending on the random arrangement of the side chains 8 of the coating film 7, the mesogenic components and the photosensitive groups of the side chains 8 are also randomly aligned, and the coating film 7 is isotropic.

In the first embodiment of the present invention, when the ultraviolet irradiation amount in the step [II] is in the range of 1% to 15% of the maximum ultraviolet irradiation amount of ΔA, the isotropic coating film 1 is irradiated with polarized ultraviolet rays. . In other words, as shown in Fig. 1(b), the photosensitive group of the side chain 2a having the photosensitive group in the side chain 2 in the direction parallel to the polarization direction of the ultraviolet light preferentially causes a photoreaction such as a dimerization reaction. . As a result, the density of the side chain 2a in which the photoreaction is performed is increased only in the direction in which the ultraviolet ray is irradiated, and as a result, the coating film 1 is applied. Give very little anisotropy.

In the first embodiment of the present invention, when the ultraviolet irradiation amount in the step [II] is in the range of 15% to 70% of the maximum ultraviolet irradiation amount, the isotropic coating film 3 is irradiated with polarized ultraviolet rays. . In this case, as shown in FIG. 2(b), the photosensitive group of the side chain 4a having the photosensitive group in the side chain 4 in the direction parallel to the polarization direction of the ultraviolet light preferentially causes a dimerization reaction or the like. reaction. As a result, the density of the side chain 4a in which the photoreaction is performed is increased only in the direction in which the polarized light is irradiated with ultraviolet rays, and as a result, the coating film 3 is imparted with a very small anisotropy.

In the second aspect of the present invention, a liquid crystal alignment film using a side chain type polymer having a photoisomerization group or a light-floating rearrangement group represented by the above formula (18) is used, [II] When the ultraviolet irradiation amount of the step is ΔA within the range of 1% to 70% of the maximum ultraviolet irradiation amount, the isotropic coating film 5 is irradiated with polarized ultraviolet rays. In this case, as shown in FIG. 3(b), the photosensitive group of the side chain 6a having the photosensitive group in the side chain 6 in the direction parallel to the polarization direction of the ultraviolet light preferentially causes the light fris rearrangement or the like. The light reacts. As a result, the density of the side chain 6a in which the photoreaction is performed is increased only in the direction in which the polarized light is irradiated with ultraviolet rays, and as a result, the coating film 5 is imparted with a very small anisotropy.

In the second aspect of the present invention, a coating film of a side chain type polymer having a structure having a light-floating rearrangement group represented by the above formula (19) is used, and the ultraviolet irradiation amount ΔA in the step [II] is When the maximum ultraviolet irradiation amount is in the range of 1% to 70%, the isotropic coating film 7 is irradiated with polarized ultraviolet rays. If so, as shown in Figure 4 (b), arranged in The photosensitive group of the side chain 8a having a photosensitive group in the side chain 8 in the direction parallel to the polarizing direction of the ultraviolet light preferentially causes photoreaction such as light-floating rearrangement. As a result, the density of the side chain 8a in which the photoreaction is performed is increased only in the direction in which the polarized light is irradiated with ultraviolet rays, and as a result, the coating film 7 is given a small anisotropy.

In the first embodiment of the present invention, when the ultraviolet irradiation amount in the step [II] is in the range of 1% to 15% of the maximum ultraviolet irradiation amount, the coating film 1 after the polarized light irradiation is heated to become a liquid crystal. status. In this case, as shown in FIG. 1(c), the amount of the crosslinking reaction which occurs between the coating film 1 in the direction parallel to the direction in which the ultraviolet rays are irradiated and the vertical direction are different. In this case, since the amount of the crosslinking reaction which occurs in the direction parallel to the direction in which the ultraviolet light is irradiated is extremely small, the crosslinking reaction site functions as a plasticizer. Therefore, the liquid crystallinity in the direction perpendicular to the direction in which the ultraviolet light is irradiated is higher than the liquid crystallinity in the parallel direction, and self-organization is performed in a direction parallel to the direction in which the ultraviolet light is irradiated, and the side chain 2 containing the mesogenic component is realigned. As a result, the very small anisotropy of the coating film 1 induced by the photocrosslinking reaction increases due to heat, giving the coating film 1 a greater anisotropy.

Similarly, in the first embodiment of the present invention, when the ultraviolet irradiation amount in the step [II] is in the range of 15% to 70% of the maximum ultraviolet irradiation amount, the coating film 3 after the polarized light irradiation is heated. Liquid crystal status. In this case, as shown in FIG. 2(c), the side chain type polymer film 3 has a different amount of crosslinking reaction between the direction parallel to the direction in which the ultraviolet light is irradiated and the direction perpendicular to the vertical direction. Therefore, self-organization is performed in a direction parallel to the direction in which the ultraviolet rays are irradiated, and the side chain 4 containing the mesogenic component is realigned. As a result, the small anisotropy of the coating film 3 induced by the photocrosslinking reaction increases due to heat. Large, giving the coating film 3 a greater anisotropy.

Similarly, in the second aspect of the present invention, a coating film of a side chain type polymer having a structure of a photorefractive group or a photorefractive group represented by the above formula (18) is used. When the ultraviolet irradiation amount in the step [II] is in the range of 1% to 70% of the maximum ultraviolet irradiation amount, the coating film 5 after the polarized light irradiation is heated to be in a liquid crystal state. As a result, as shown in FIG. 3(c), the amount of the light Fres rearrangement reaction generated between the coating film 5 and the direction parallel to the direction in which the ultraviolet rays are irradiated is different. In this case, the liquid crystal alignment force of the Fres rearrangement body generated in the direction perpendicular to the polarization direction of the ultraviolet ray is stronger than the liquid crystal alignment force of the side chain before the reaction, so that it is perpendicular to the polarization direction of the ultraviolet ray. Self-organization causes the side chain 6 containing the mesogenic component to realign. As a result, the very small anisotropy of the coating film 5 induced by the Frestle rearrangement reaction increases due to heat, giving the coating film 5 a greater anisotropy.

In the second embodiment of the present invention, a coating film using a side chain type polymer having a structure of a light Fres rearrangement group represented by the above formula (19) is used, and the ultraviolet irradiation amount in the step [II] is used. When ΔA is in the range of 1% to 70% of the maximum ultraviolet irradiation amount, the coating film 7 after the polarized light irradiation is heated to be in a liquid crystal state. As a result, as shown in FIG. 4(c), the side chain type polymer film 7 has a different amount of light Fres rearrangement reaction between the direction parallel to the direction in which the ultraviolet light is irradiated and the vertical direction. Since the anchor force of the light Frye rearrangement body 8 (a) is stronger than the side chain 8 of the front row, a certain amount of light floes rearrangement is generated, and ultraviolet rays are irradiated. Self-grouping in a direction parallel to the direction of polarization The weaving realigns the side chain 8 containing the mesogenic component. As a result, the small anisotropy of the coating film 7 induced by the Fleet rearrangement reaction is increased by heat, and the coating film 7 is imparted with greater anisotropy.

Therefore, the coating film used in the method of the present invention is obtained by sequentially irradiating the coating film with polarized ultraviolet rays and heat treatment, and introducing the anisotropic property with high efficiency, thereby providing a liquid crystal alignment film excellent in alignment control energy.

Therefore, the coating film used in the method of the present invention is optimized for the amount of polarized ultraviolet light applied to the coating film and the heating temperature of the heat treatment. Thereby, the anisotropic introduction of the coating film can be achieved more efficiently.

The irradiation amount of the optimum polarized ultraviolet ray when the anisotropic property is introduced into the coating film used in the present invention is efficiently carried out in accordance with the photo-crosslinking reaction or photoisomerization reaction of the photosensitive group in the coating film, or light Frye The amount of polarized ultraviolet light that is optimal for the amount of rearrangement reaction. When the coating film used in the present invention is irradiated with polarized ultraviolet light, when the photocrosslinking reaction, the photoisomerization or the reaction, or the photoreceptor group of the side chain of the optical Fress rearrangement reaction is small, sufficient photoreactivity cannot be obtained. . In this case, sufficient self-organization cannot be performed even after subsequent heating. On the other hand, in the coating film used in the present invention, as a result of irradiating the polarized ultraviolet light to the structure having the photocrosslinkable group, when the photosensitive group of the side chain of the crosslinking reaction is excessive, the crosslinking reaction between the side chains is excessive. get on. In this case, the obtained coating film becomes rigid, and there is a case where the self-organization of the subsequent heating is hindered. Further, in the coating film used in the present invention, when the structure having the light Fress rearrangement group is irradiated with the polarized ultraviolet light, the photosensitive layer of the side chain of the light-recovering reaction is excessively applied, and the coating film is formed. The liquid crystal property is excessively lowered. In this case, the liquid crystallinity of the obtained film also drops. Low, there will be situations that hinder the subsequent self-organization of heating. Further, when the ultraviolet ray is irradiated with ultraviolet light when the ultraviolet ray irradiation amount is too large, the side chain type polymer is photodecomposed, and the self-organization of the subsequent heating is hindered. Happening.

Therefore, in the coating film used in the present invention, the photosensitive group of the side chain is subjected to a photocrosslinking reaction, a photoisomerization reaction, or an optical Fress rearrangement reaction by irradiation with polarized ultraviolet rays. Preferably, the side chain type polymer film has a photosensitive group of 0.1 mol% to 40 mol%, more preferably 0.1 mol% to 20 mol%. By setting the amount of the photosensitive group of the side chain in which the photoreaction is carried out within this range, the subsequent self-organization by the heat treatment can be efficiently performed, and the anisotropy can be efficiently formed in the film.

The coating film used in the method of the present invention is optimized for the amount of irradiation of ultraviolet light by polarization, and the photocrosslinking reaction or photoisomerization reaction or light of the photosensitive group in the side chain of the side chain type polymer film is obtained. The amount of Fres rearrangement reaction is optimized. Therefore, the introduction of the anisotropic property to the coating film used in the present invention can be efficiently achieved together with the subsequent heat treatment. In this case, the amount of the suitable polarized ultraviolet rays can be evaluated based on the evaluation of the ultraviolet absorption of the coating film used in the present invention.

That is, the coating film used in the present invention is measured for ultraviolet absorption in the direction parallel to the polarization direction of the polarized ultraviolet light and ultraviolet absorption in the vertical direction after the polarized ultraviolet light irradiation. From the measurement results of the ultraviolet absorption, 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 vertical direction (that is, ΔA) was evaluated. Next, the ΔA achieved in the coating film used in the present invention was determined. The maximum value (ΔAmax) and the amount of polarized ultraviolet light that achieves it. In the production method of the present invention, the amount of polarized ultraviolet light which is preferably irradiated in the production of the liquid crystal alignment film can be determined based on the amount of the polarized ultraviolet ray which is obtained by the ΔAmax.

In the production method of the present invention, it is preferred that the amount of the polarized ultraviolet light applied to the coating film used in the present invention is in the range of 1% to 70% of the amount of the polarized ultraviolet light which achieves ΔAmax, more preferably 1% to 50%. Within the range of %. In the coating film used in the present invention, the amount of the polarized ultraviolet ray in the range of 1% to 50% of the amount of the polarized ultraviolet ray of ΔAmax is equivalent to the photosensitive base of the side chain type polymer film. 0.1 mol% to 20 mol% The amount of polarized ultraviolet light for photocrosslinking reaction.

In the production method of the present invention, in order to achieve high-efficiency anisotropy introduction of the coating film, a suitable heating temperature may be determined as described above based on the liquid crystal temperature range of the side chain type polymer. Therefore, for example, when the liquid crystal temperature range of the side chain type polymer used in the present invention is from 100 ° C to 200 ° C, the heating temperature after the polarized ultraviolet light irradiation is preferably from 90 ° C to 190 ° C. Thereby, the coating film used in the present invention can impart greater anisotropy.

As such, the liquid crystal display element provided by the present invention exhibits high reliability against external stress such as light or heat.

As described above, the substrate for a lateral electric field drive type liquid crystal display device manufactured by the method of the present invention or the lateral electric field drive type liquid crystal display device having the substrate is excellent in reliability, and can be suitably used for a large-screen and high-definition liquid crystal. TV, etc.

Hereinafter, the present invention will be described by way of examples, but the invention is not limited by the examples.

[Examples]

The abbreviation used in the examples is as follows.

(methacrylic monomer)

MA1 is synthesized by the synthesis method described in the patent document (WO2011/084546).

<organic solvent>

THF: tetrahydrofuran

NEP: N-ethyl-2-pyrrolidone

PB: propylene glycol monobutyl ether

DIBC: 2,6-dimethyl-4-heptanol

<Polymerization initiator>

AIBN: 2,2'-azobisisobutadiene

<Polymer Synthesis>

MA1 (9.97 g, 30.0 mmol) was dissolved in THF (92.0 g) After degassing with a diaphragm pump, AIBN (0.246 g, 1.5 mmol) was added and degassed again. Subsequently, the reaction was carried out at 50 ° C for 30 hours to obtain a polymer solution of methacrylate. The polymer solution was added dropwise to diethyl ether (1000 ml), and the resulting precipitate was filtered. The precipitate was washed with diethyl ether and dried under reduced pressure in an oven at 40 ° C to obtain a methacrylate polymer powder (A). The polymer had a number average molecular weight of 16,000 and a weight average molecular weight of 32,000.

The liquid phase phase transition temperature of the obtained methacrylate polymer is from 145 ° C to 190 ° C.

<Example 1>

NEP (49.0 g) was added to the obtained methacrylate polymer powder (A) (6.0 g), and the mixture was stirred at room temperature for 5 hours to dissolve. In this solution, PB (20.0 g) and DIBC (25.0 g) were added and stirred to obtain a liquid crystal alignment agent (A1).

<Example 2>

NEP (49.0 g) was added to the obtained methacrylate polymer powder (A) (6.0 g), and the mixture was stirred at room temperature for 5 hours to dissolve. In this solution, PB (10.0 g) and DIBC (35.0 g) were added and stirred to obtain a liquid crystal alignment agent (A2).

<Example 3>

Adding NEP (49.0 g) to the obtained methacrylate polymer The powder (A) (6.0 g) was dissolved by stirring at room temperature for 5 hours. In this solution, a liquid crystal alignment agent (A3) was obtained by adding DIBC (45.0 g) and stirring.

<Comparative Example 1>

NEP (49.0 g) was added to the obtained methacrylate polymer powder (A) (6.0 g), and the mixture was stirred at room temperature for 5 hours to dissolve. Into this solution, PB (45.0 g) was added and stirred to obtain a liquid crystal alignment agent (Comparative Example 1).

The liquid crystal alignment agent obtained in the examples of the present invention was used to evaluate the inkjet coating properties of the liquid crystal alignment agent. This condition is as follows.

The liquid crystal alignment agent (A1) obtained in Example 1 of the present invention, the liquid crystal alignment agent (A2) obtained in Example 2, the liquid crystal alignment agent (A3) obtained in Example 3, and the liquid crystal obtained in Comparative Example 1 The alignment agent (Comparative Example 1) was subjected to pressure filtration through a membrane filter having a pore size of 1 μm to evaluate the inkjet coating properties.

HIS-200 (manufactured by Hitachi Plant Technologies Co.) was used as the inkjet coater. The coating was applied to an ITO (Indium Tin Oxide) vapor-deposited substrate which had been washed with pure water and IPA (isopropyl alcohol) to have a coating area of 80×72 mm, a nozzle pitch of 0.423 mm, and a scanning pitch of 0.5 mm. The cloth speed was 40 mm/sec, the time from the application to the temporary drying was 30 seconds, and the temporary drying was carried out on a hot plate at 70 ° C for 90 seconds.

Regarding the obtained liquid crystal alignment film, a liquid crystal alignment film is performed. The evaluation of "the linearity of the end" and the "uplift of the end".

The evaluation of the linearity of the end portion of the liquid crystal alignment film is a liquid crystal alignment film having a right end portion in the printing direction, and is observed by an optical microscope (ECLIPSE ME600 manufactured by Nikon Corporation). Specifically, the difference between (1) and (2) in FIG. 5 of the liquid crystal alignment film image observed by an optical microscope at a magnification of 25 times, that is, the length of A in FIG. 5 was measured. Here, (2) of FIG. 5 shows the end portion of the right maximum region when the liquid crystal alignment film having the right end portion in the printing direction is observed by an optical microscope; on the other hand, (1 of FIG. 5) When the same observation is made by an optical microscope, the end portion of the smallest area on the right side is expanded. At this time, all the images of the liquid crystal alignment film were obtained at the same magnification. When the length of the A is shorter, it is evaluated that the linearity of the end portion of the liquid crystal alignment film is superior.

The evaluation of the bulging of the end portion of the liquid crystal alignment film is a liquid crystal alignment film at the right end portion in the printing direction, and is observed by an optical microscope. Specifically, the length of B in Fig. 6 was measured by an optical microscope at a magnification of 25 times and a liquid crystal alignment film image was obtained. Here, FIG. 6 is a view schematically showing a ridge of the liquid crystal alignment film observed at the right end portion in the printing direction, and is schematically shown by hatching. At this time, all the images of the liquid crystal alignment film were obtained at the same magnification. The evaluation was such that the shorter the length of B, the more excellent the ridge of the end portion of the liquid crystal alignment film was judged.

The results are as shown in the table below. Table 2 shows the length of A and the length of B of the liquid crystal alignment film obtained in the examples. Still, Table 1 The ratio of the organic solvent in the solvent is 6% by mass, so the ratio of the solvent is expressed by the mass ratio among the remaining 94%.

From the above results, it is understood that the liquid crystal alignment film obtained by the liquid crystal alignment agent of the embodiment (invention) has high linearity at the end portion of the liquid crystal alignment film and small bulging at the end portion of the liquid crystal alignment film.

1‧‧‧Side chain polymer film

2, 2a‧‧‧ side chain

Claims (15)

A polymer composition comprising a polymer composition of the following composition [I]: (A) a photosensitive side chain type polymer exhibiting liquid crystallinity in a specific temperature range, and (B) diisobutylmethanol ( Diisobutyl carbinol), and (C) organic solvent. The composition of claim 1, wherein the component (A) has a photosensitive side chain which causes photocrosslinking, photoisomerization, or Fries rearrangement. The composition of claim 1 or 2, wherein the component (A) has any one of photosensitive side chains selected from the group consisting of the following formulas (1) to (6): (wherein A, B, and D each independently represent a single bond, -O-, -CH ₂ -, -COO-, -OCO-, -CONH-, -NH-CO-, -CH=CH-CO-O -, or -O-CO-CH=CH-; S is an alkylene group having 1 to 12 carbon atoms, and the hydrogen atom bonded to the hydrogen atom may be substituted with a halogen group; T is a single bond or a carbon number of 1~ a alkyl group of 12, and a hydrogen atom bonded to the hydrogen atom may be substituted with a halogen group; Y ₁ represents a benzene ring selected from a monovalent group, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring, and a carbon number of 5~ a ring of 8 alicyclic hydrocarbons, or a group of 2 to 6 ring systems selected from the same or different substituents bonded through the bonding group B, and the hydrogen atoms bonded to the substituents may be independently Is -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, Substituting an alkyl group having 1 to 5 carbon atoms or an alkyloxy group having 1 to 5 carbon atoms; Y ₂ is selected from a bivalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring, and a carbon number of 5. a group of ~8 alicyclic hydrocarbons, and a combination of such groups, the hydrogen atoms bonded to the hydrogen atoms may be independently independently -NO ₂ , -CN, -CH=C(CN) ₂ , -CH =CH-CN, halo, alkyl 1 to 5, or carbon number 1 Substituted with an alkyloxy group of ~5; R represents a hydroxyl group, an alkoxy group having 1 to 6 carbon atoms, or represents the same definition as Y ₁ ; X represents a single bond, -COO-, -OCO-, -N=N -, -CH=CH-, -C≡C-, -CH=CH-CO-O-, or -O-CO-CH=CH-, X may be the same or different when X is 2; Cou Representing a coumarin-6-yl or coumarin-7-yl group, and the hydrogen atoms bonded to the hydrogen atoms may be independently independently -NO ₂ , -CN, -CH=C(CN) ₂ , -CH=CH -CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or an alkyloxy group having 1 to 5 carbon atoms; one of q1 and q2 is 1 and the other is 0; q3 is 0 or 1; P and Q are each independently 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 a combination thereof. However, when X is -CH=CH-CO-O- and -O-CO-CH=CH-, P or Q on the side of the bond of -CH=CH- is an aromatic ring, and when the number of P is 2 or more P may be the same or different from each other. When the number of Q is 2 or more, Q may be the same or different; 11 is 0 or 1; 12 is an integer of 0 to 2; when both 11 and 12 are 0, T is a single A also indicates a single bond when the key is; when 11 is 1, B is also a single bond when T is a single bond; H and I are each independently A base selected from the group consisting of a divalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring, and combinations thereof. The composition according to any one of claims 1 to 3, wherein the component (A) has any one of photosensitive side chains selected from the group consisting of the following formulas (7) to (10): (wherein A, B, and D each independently represent a single bond, -O-, -CH ₂ -, -COO-, -OCO-, -CONH-, -NH-CO-, -CH=CH-CO-O -, or -O-CO-CH=CH-; Y ₁ represents a ring selected from the group consisting of a monovalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring, and an alicyclic hydrocarbon having 5 to 8 carbon atoms. Or the same or different 2~6 ring systems selected from the substituents are bonded through a bond group B, and the hydrogen atoms bonded to the hydrogen atoms may be independently independently -COOR ₀ (where 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, an alkyl group having 1 to 5 carbon atoms, Or substituted with an alkyloxy group having 1 to 5 carbon atoms; X represents a single bond, -COO-, -OCO-, -N=N-, -CH=CH-, -C≡C-, -CH=CH- CO-O-, or -O-CO-CH=CH-, X may be the same or different when X is 2; l represents an integer from 1 to 12; m represents an integer from 0 to 2, and m1 and m2 represent An integer from 1 to 3; n represents an integer from 0 to 12 (but B is a single bond when n = 0); Y ₂ is selected from a bivalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring, carbon a group of 5 to 8 alicyclic hydrocarbons, and a group of the combinations of the groups, the hydrogen atoms bonded to the hydrogen atoms may be independently -N O 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; A hydroxyl group, an alkoxy group having 1 to 6 carbon atoms, or a definition identical to Y ₁ ). The composition according to any one of claims 1 to 3, wherein the component (A) has a photosensitive side chain selected from the group consisting of the following formulas (11) to (13): (wherein A each independently represents a single bond, -O-, -CH ₂ -, -COO-, -OCO-, -CONH-, -NH-CO-, -CH=CH-CO-O-, or - O-CO-CH=CH-; X represents a single bond, -COO-, -OCO-, -N=N-, -CH=CH-, -C≡C-, -CH=CH-CO-O-, Or -O-CO-CH=CH-, X may be the same or different when X is 2; l represents an integer from 1 to 12, m represents an integer from 0 to 2, and m2 represents an integer from 1 to 3; And a ring selected from the group consisting of a monovalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring, and an alicyclic hydrocarbon having 5 to 8 carbon atoms, or the same or different 2 to 6 selected from the substituents The ring system is bonded to the group formed by the bonding group B, and the hydrogen atoms bonded to the hydrogen atoms may be 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, an alkyl group having 1 to 5 carbon atoms, or an alkyloxy group having 1 to 5 carbon atoms, or Represents a hydroxyl group or an alkoxy group having 1 to 6 carbon atoms). The composition according to any one of claims 1 to 3, wherein the component (A) has a photosensitive side chain represented by the following formula (14) or (15): (wherein A each independently represents a single bond, -O-, -CH ₂ -, -COO-, -OCO-, -CONH-, -NH-CO-, -CH=CH-CO-O-, or - O-CO-CH=CH-; Y ₁ represents a ring selected from a monovalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring, and an alicyclic hydrocarbon having 5 to 8 carbon atoms, or The substituents selected from the same or different substituents of 2 to 6 ring systems are bonded through a bond group B, and the hydrogen atoms bonded to the hydrogen atoms may be independently independently subjected to -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, an alkyl group having 1 to 5 carbon atoms, or a carbon number of 1 Substituted by an alkyloxy group of ~5; X represents a single bond, -COO-, -OCO-, -N=N-, -CH=CH-, -C≡C-, -CH=CH-CO-O- Or, -O-CO-CH=CH-, X may be the same or different when X is 2; l represents an integer from 1 to 12, and m1 and m2 represent integers from 1 to 3). The composition according to any one of claims 1 to 3, wherein the component (A) has a photosensitive side chain represented by the following formula (16) or (17): (wherein A represents a single bond, -O-, -CH ₂ -, -COO-, -OCO-, -CONH-, -NH-CO-, -CH=CH-CO-O-, or -O- CO-CH=CH-; X represents a single bond, -COO-, -OCO-, -N=N-, -CH=CH-, -C≡C-, -CH=CH-CO-O-, or - O-CO-CH=CH-, X may be the same or different when X is 2; l represents an integer from 1 to 12, and m represents an integer from 0 to 2). The composition according to any one of claims 1 to 3, wherein the component (A) has a photosensitive side chain selected from any one of the group consisting of the following formula (18) or (19): (wherein A and B each independently represent a single bond, -O-, -CH ₂ -, -COO-, -OCO-, -CONH-, -NH-CO-, -CH=CH-CO-O-, Or -O-CO-CH=CH-; Y ₁ represents a ring selected from the group consisting of a monovalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring, and an alicyclic hydrocarbon having 5 to 8 carbon atoms, or The substituents selected from the same or different 2 to 6 ring systems are bonded through a bond group B, and the hydrogen atoms bonded to the hydrogen atoms may be independently 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, an alkyl group having 1 to 5 carbon atoms, or carbon Substituted by an alkyloxy group of 1 to 5; one of q1 and q2 is 1 and the other is 0; l represents an integer of 1 to 12, m1 and m2 represent an integer of 1 to 3; and 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). The composition according to any one of claims 1 to 3, wherein the component (A) has a photosensitive side chain represented by the following formula (20): (wherein A represents a single bond, -O-, -CH ₂ -, -COO-, -OCO-, -CONH-, -NH-CO-, -CH=CH-CO-O-, or -O- CO-CH=CH-; Y ₁ represents a ring selected from a monovalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring, and an alicyclic hydrocarbon having 5 to 8 carbon atoms, or a substituent thereof The same or different 2~6 ring systems are selected by a bond group B, and the hydrogen atoms bonded to the hydrogen atoms may be independently -COOR ₀ (wherein R ₀ represents a hydrogen atom or carbon) a number of 1 to 5 alkyl groups, -NO ₂ , -CN, -CH=C(CN) ₂ , -CH=CH-CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or a carbon number of 1 to 5 Substituted by an alkyloxy group; X represents a single bond, -COO-, -OCO-, -N=N-, -CH=CH-, -C≡C-, -CH=CH-CO-O-, or -O-CO-CH=CH-, X may be the same or different when X is 2; l represents an integer from 1 to 12, and m represents an integer from 0 to 2). The composition according to any one of claims 1 to 9, wherein the component (A) has any one of liquid crystal side chains selected from the group consisting of the following formulas (21) to (31): (wherein A and B have the same definitions as above; Y ₃ is selected from the group consisting of a monovalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a nitrogen-containing hetero ring, and an alicyclic hydrocarbon having 5 to 8 carbon atoms. And a group of such groups, the hydrogen atoms bonded to the hydrogen atoms may be independently -NO ₂ , -CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or a carbon number of 1 to 5 Substituted by an alkyloxy group; R ₃ represents a hydrogen atom, -NO ₂ , -CN, -CH=C(CN) ₂ , -CH=CH-CN, a halogen group, a monovalent benzene ring, a naphthalene ring, a combination a benzene ring, a furan ring, a nitrogen-containing hetero ring, an alicyclic hydrocarbon having 5 to 8 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms; one of q1 and q2 is 1 The other is 0; l represents an integer from 1 to 12, and m represents an integer from 0 to 2, but in equations (25) to (26), the total of all m is 2 or more, and equations (27) to (28) In the above, the total of all m is 1 or more, and m1, m2, and m3 each independently represent an integer of 1 to 3; and R ₂ represents a hydrogen atom, -NO ₂ , -CN, a halogen group, a monovalent benzene ring, a naphthalene ring, and a combination. a benzene ring, a furan ring, a nitrogen-containing hetero ring, and an alicyclic hydrocarbon having 5 to 8 carbon atoms, and an alkyl group or an alkyloxy group; Z ₁ and Z ₂ represent a single bond, -CO-, -CH ₂ O- , -CH=N-, -CF ₂ -). A method for producing a substrate having a liquid crystal alignment film, wherein the liquid crystal alignment film is obtained by the following steps to obtain a liquid crystal alignment film for a lateral electric field-driven liquid crystal display element which imparts alignment control energy: [I] as in claim 1 a step of applying a composition of any one of the above-mentioned 10 to a substrate having a conductive film for driving a transverse electric field to form a coating film; [II] a step of irradiating the coating film obtained in [I] with a polarized ultraviolet ray; [III] A step of heating the coating film obtained in [II]. A substrate having a method as claimed in claim 11 A liquid crystal alignment film for a lateral electric field drive type liquid crystal display element. A lateral electric field drive type liquid crystal display element having the substrate as claimed in claim 12. A method of manufacturing a liquid crystal display device, comprising: obtaining a lateral electric field drive type liquid crystal display element by the following steps: preparing a substrate (first substrate) as claimed in claim 12; and obtaining a second substrate having a liquid crystal alignment film In the step, the liquid crystal alignment film imparting the alignment control energy is obtained by the following steps [I'] to [III']: [I'] is coated on the second substrate as in any one of claims 1 to 11. a step of forming a coating film by the composition; [II'] a step of irradiating the coating film obtained in [I'] with a polarized ultraviolet ray; and [III'] a step of heating the coating film obtained in [II']; And [IV] a step of obtaining a liquid crystal display device in which the first and second substrates are opposed to each other such that the liquid crystal alignment films of the first and second substrates face each other with a liquid crystal. A transverse electric field driven liquid crystal display element manufactured by the method of claim 14.