JP2007094071A - Photo-alignment layer composition and method for manufacturing photo-alignment layer - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To obtain a photo-alignment layer giving large anchoring force with a low luminous energy. <P>SOLUTION: The photo-alignment layer composition contains an azo compound expressed by general formula (1) and a polymerizable compound expressed by general formula (2). The method for manufacturing the photo-alignment layer comprises applying the above photo-alignment layer composition on a substrate, irradiating the coating film with light having anisotropy, and heating the composition at 100 to 200°C. In the formulae, A<SP>1</SP>to A<SP>4</SP>and X<SP>a</SP>, X<SP>b</SP>represent substituents, R<SP>2</SP>, R<SP>3</SP>, Y<SP>1</SP>, Y<SP>2</SP>represent linking groups as combined, and Q<SP>1</SP>and Q<SP>2</SP>represent reactive functional groups. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to a method for producing a liquid crystal alignment film, and more specifically, production of a liquid crystal alignment film (hereinafter abbreviated as a photo-alignment film) capable of aligning liquid crystal molecules without being rubbed by irradiating light. Regarding the method.

In the liquid crystal display device, the state of the molecular arrangement of the liquid crystal is changed by the action of an electric field or the like, and the change in the optical characteristics accompanying this is used for display. In many cases, the liquid crystal is used by being injected into a gap between two substrates. In order to align the liquid crystal molecules in a specific direction, an alignment process is performed on the inside of the substrate.
Conventionally, in many cases, a method called rubbing, in which a polymer film such as polyimide is provided on a substrate such as glass and is rubbed in one direction with a cloth or the like, is used for alignment treatment. As a result, the liquid crystal molecules are aligned so that their molecular axes are parallel to the rubbed direction. However, in the rubbing method, fine scratches on the surface of the polymer film due to mechanical rubbing may cause liquid crystal alignment defects, and uneven alignment may occur due to non-uniform pressing pressure during rubbing. There is a problem that the definition of the liquid crystal element is lowered.

In order to solve such a problem, a liquid crystal alignment film manufacturing technique that does not perform rubbing has recently attracted attention. In particular, the photo-alignment method, which obtains liquid crystal alignment by irradiating the coating film provided on the substrate with light having some anisotropy, is expected to be put to practical use because of its excellent mass productivity and compatibility with large substrates. ing.
Examples of such photo-alignment films include anisotropic photolysis such as azobenzene derivatives such as azobenzene derivatives, compounds that undergo photodimerization reactions such as cinnamate, coumarin, and chalcone, and polyimides that have sites that generate photodimerization reactions. The resulting compound is known, and recently, a photo-alignment film using a dichroic compound and a radical polymerizable monomer having a mesogenic group that satisfies liquid crystal alignment performance (order parameter) and light resistance (for example, Patent Document 1), a photo-alignment film using a specific azo compound having a polymerizable group (see, for example, Patent Documents 2 and 3), and the like are known.

  However, all of these photo-alignment films are inferior to the rubbing alignment film in the ability of the photo-alignment film to align the liquid crystal (also referred to as alignment regulating force or anchoring force), and particularly requires a large azimuth anchoring energy. It has been difficult to apply to an IPS (in-plane switching) type liquid crystal display element.

JP 2003-270638 A JP 2002-250924 A JP 2004-302272 A

  The problem to be solved by the present invention is to provide a photo-alignment film composition for obtaining a photo-alignment film capable of obtaining a large anchoring force with a small amount of light, and a method for producing this photo-alignment film using the same. It is in.

  As a result of intensive studies, the inventors have applied a composition containing a polymerizable compound having a tolan skeleton and a compound having an azobenzene skeleton having a specific structure on a substrate, and then the coating film has anisotropy. It has been found that the above-mentioned problems can be solved by irradiating with light and then heating.

  That is, this invention provides the composition for photo-alignment films containing the azo compound represented by General formula (1), and the polymeric compound represented by General formula (2).

(In General Formula (1), A ¹ and A ² are each independently a hydrogen atom, a halogen atom, a carboxy group, a halogenated methyl group, a halogenated methoxy group, a cyano group, a hydroxymethyl group, a hydroxyl group, —OR ^1. (However, R ¹ is an alkyl group having 2 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a C 1-6 carbon atom substituted with a lower alkoxy group having 1 to 6 carbon atoms. The carboxy group may form a salt with an alkali metal, and A ³ and A ⁴ are each independently a carboxy group, a sulfo group, an amino group, a hydroxy group, or a carbamoyl group. Represents a sulfamoyl group and a methyloxycarbonyl group, provided that the carboxy group and the sulfo group may form a salt with an alkali metal.
In General Formula (2), ^Xa and ^Xb each independently represent a hydrogen atom, a fluorine atom, a chlorine atom, or a methyl group, and l and m each represent an integer of 0 to 4. However, at least one of l and m is an integer of 1 or more. Z represents an aromatic hydrocarbon group or an alicyclic hydrocarbon group which may be substituted with one or more fluorine atoms, chlorine atoms or methyl groups. q and t each independently represent an integer of 1 to 20, and R ² and R ³ each independently represent a linear or branched divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms. Y ¹ and Y ² each independently represent a linking group selected from the group consisting of a single bond, —O—, —S—, —O—CO— or —CO—O—, and Q ¹ And Q ² are each independently acryloyloxy group, methacryloyloxy group, ClCH═CHCOO—, acrylamide group, methacrylamide group, ClCH═CHCONH—, vinyl group, CH ₂ ═CCl—, CHCl═CH—, epoxy Represents a reactive functional group selected from the group consisting of a group, an ethynyl group, a mercapto group, CH ₂ ═CHO— or a maleimide group. )

  Further, the present invention provides an optical material having anisotropy in a method for producing a photoalignment film in which the composition for photoalignment film described above is applied onto a substrate, and then the coating film is irradiated with light having anisotropy. After the irradiation, a method for producing a photo-alignment film that is heated at 100 to 200 ° C. is provided.

  According to the composition and manufacturing method for a photoalignment film of the present invention, a photoalignment film having a large anchoring force for liquid crystals can be obtained, and a photoalignment film having excellent mass productivity, wide application range, and high practicality can be obtained. be able to.

  In the present invention, the azo compound represented by the general formula (1) has dichroism with respect to polarized light, and is irradiated with anisotropy light so that it is constant with respect to the vibration direction or incident direction of light. And in a direction with a relatively small dose.

In the general formula (1), when A ¹ or A ² is a carboxy group, a halogenated methyl group, or more particularly a trifluoromethyl group, they are arranged in a certain direction with a small amount of light having anisotropy. And the ability to arrange the polymerizable compound described later is large, which is particularly preferable.

In the general formula (1), when A ³ or A ⁴ is a sulfo group, it has an ability to arrange anisotropy in a certain direction with a small irradiation amount of light and to arrange a polymerizable compound described later. Large and particularly preferred. In this case, it is more preferable that the substitution position of the sulfo group is 2, 2 ′ with respect to the biphenyl skeleton, since these capabilities are even greater.

In general formula (2), X ^a and X ^b are preferably fluorine atoms.

  In the general formula (2), l and m are more preferably a compound in which l is 0, m is an integer of 0 to 2, and m is 1.

  As an aromatic hydrocarbon group of Z which is an aromatic hydrocarbon group or an alicyclic hydrocarbon group which may be substituted with one or more fluorine atoms, chlorine atoms or methyl groups in the general formula (2) Examples thereof include a phenylene group and a naphthalene group. The alicyclic hydrocarbon group is preferably a 6-membered ring, and examples thereof include a cyclohexylene group. Z is particularly preferably a phenylene group.

  In general formula (2), q and t are each preferably a compound having an integer of 1 to 10, particularly preferably a compound having an integer of 1 to 5, more preferably a compound having an integer of 1 to 3. Certain compounds are most preferred.

In the general formula (2), R ² and R ³ are each preferably a linear or branched alkylene group having 1 to 18 carbon atoms or an alkenylene group, and more preferably an alkylene group.

In general formula (2), Y ¹ and Y ² are each preferably a single bond or a compound having —O—, and more preferably a compound having a single bond.

In the general formula (2), when Q ¹ and Q ² are maleimide groups, a polymerization initiator is not required for the polymerization reaction, and polymerization inhibition by oxygen hardly occurs, so that the polymerization reaction can be performed in the atmosphere. Is particularly preferred.

The polymerizable compound represented by the general formula (2) is considered to be arranged by being induced by light rearrangement by irradiation with light having anisotropy of the azo compound of the general formula (1). The polymerizable compound represented by the general formula (2) arranged is considered to have a large anchoring force with respect to the liquid crystal molecules, and it is considered that good liquid crystal alignment can be obtained.
In the present invention, since the polymerizable compound represented by the general formula (2) has a reactive functional group, the arrangement is fixed by heating, and a photo-alignment film with higher photostability is obtained.
Since the compound represented by the general formula (1) and the polymerizable compound represented by the general formula (2) used in the present invention are both transparent to visible light and near ultraviolet light, they are highly transparent. A photo-alignment film is obtained.

Although it is not clear why a large anchoring force can be obtained by adding the polymerizable compound represented by the general formula (2) having a tolan skeleton, the general formula having a tolan skeleton at the time of light irradiation ( The polymerizable compound represented by 2) is arranged by being guided by rearrangement of the azo compound represented by the general formula (1), and is arranged according to the tran skeleton of the polymerizable compound represented by the general formula (2). An effect or a synergistic effect of the tran skeleton of the polymerizable compound represented by the general formula (2) and the azo compound represented by the general formula (1) can provide a large anchoring force for liquid crystal molecules. It is estimated.
This effect cannot be obtained with a skeleton generally called a mesogenic group such as a biphenyl skeleton or a cyclohexylphenyl skeleton, and is an effect characteristically seen only with a tolan skeleton.
In addition, when a compound having a tolan skeleton but no polymerizable group is added, no effect is obtained. This is presumably because the compound having a tolan skeleton is not immobilized in the photo-alignment film, and thus dissolves when in contact with the liquid crystal.

The content of the compound represented by the general formula (2) is preferably in the range of 10 to 70% by mass, more preferably in the range of 20 to 60%, and particularly preferably in the range of 40 to 60%.
When the content of the compound represented by the general formula (2) is too small, a sufficiently large anchoring force may not be obtained, and when the content is too large, the components are rearranged relatively by light irradiation. The content of the azo compound represented by the general formula (1) is reduced, and as a result, in order to impart liquid crystal alignment to the photo-alignment film, a larger amount of light may be required.

After apply | coating on the board | substrate, the composition for photo-alignment films of this invention provides liquid crystal orientation by irradiating the light which has anisotropy to the obtained coating film. Thereafter, the polymerizable compound represented by the general formula (2) is thermally polymerized to fix the molecular arrangement in the photo-alignment film, thereby obtaining a photo-alignment film having high photostability.
Since the heating temperature at the time of thermal polymerization is too high, there is a concern that each compound constituting the alignment film may be thermally decomposed to adversely affect the electrical characteristics of the liquid crystal element. A range of 140 to 190 ° C. is particularly preferable.
At this time, a thermal polymerization initiator can be added for the purpose of improving the thermal polymerization reaction. Examples of the thermal polymerization initiator include benzoyl peroxide and azobisisobutyronitrile. The addition amount of the polymerization initiator is preferably 10% by weight or less, more preferably 5% by weight or less, with respect to the polymerizable compound represented by the general formula (2). A range of 5% by weight is particularly preferred.

  The substrate on which the composition for photo-alignment film of the present invention is applied can be used regardless of an organic material or an inorganic material. Examples of the material constituting the substrate include inorganic materials such as glass, silicon, and quartz, and organic materials such as polyethylene terephthalate, polycarbonate, triacetyl cellulose, and polysulfone. These substrates may be provided with electrode layers such as ITO, Cr, and Al.

The composition for photo-alignment films of the present invention is usually dissolved in a solvent and applied on a substrate with a solution. Examples of the application method include spin coating, die coating, gravure coating, flexographic printing, and printing methods such as inkjet. The solvent to be used is not particularly limited as long as it can dissolve the composition for photo-alignment film of the present invention. However, in order to apply by the above method, the vapor pressure at a relatively room temperature is relatively low, and a solvent having a high boiling point is used. easy to handle. Examples thereof include N-methylpyrrolidone, butoxyethanol, γ-butyrolactone, ethylene glycol, propylene glycol, 2-pyrrolidone, N, N-dimethylformamide, phenoxyethanol, butanol, isopropyl alcohol, and water. These solvents may be appropriately mixed and used in consideration of the solubility of each compound in the composition of the present invention and the wettability to the substrate.
The film thickness is not particularly limited, but it is usually applied so that the film thickness after coating and drying is in the range of 10 to 100 nm.

  The composition for photo-alignment films of the present invention may use various additives as long as the effects of the present invention are not impaired. Examples of the additive include a silane coupling agent for improving adhesion to a substrate such as glass and a leveling agent for obtaining a uniform coating film.

The solution of the composition for photo-alignment film applied to the substrate is volatilized by heating, and then irradiated with light having anisotropy to obtain a photo-alignment film having liquid crystal orientation. The heating temperature at this time is preferably such a temperature that the polymerizable group of the composition for photo-alignment film is not polymerized.
Further, as the light having anisotropy, polarized light or non-polarized light incident from an oblique direction with respect to the film surface can be used, and the polarized light can be linearly polarized light or elliptically polarized light. On the other hand, when irradiating non-polarized light from an oblique direction with respect to the film surface, it is preferably substantially parallel light, and near ultraviolet light of 350 nm to 400 nm is particularly preferable. Examples of the light source include a xenon lamp, a high-pressure mercury lamp, an ultrahigh-pressure mercury lamp, a metal halide lamp, and an ultraviolet laser using KrF or ArF. Ultraviolet light or visible light obtained from such a light source may be irradiated using an interference filter, a color filter, or the like to limit the wavelength range of irradiation. Moreover, linearly polarized light can be obtained by using a polarizing filter or a polarizing prism for the light from these light sources.

In the method for producing a photo-alignment film of the present invention, for the thermal polymerization of the polymerizable compound represented by the general formula (2), after irradiation with anisotropic light, heating is performed at 100 to 200 ° C. Heating is performed in air, in an N ₂ or Ar atmosphere, or in vacuum.

  Hereinafter, although an example and a comparative example explain the present invention, the present invention is not limited to these. Unless otherwise specified, “part” and “%” are based on mass.

（ａ）

(A)

（ｂ）

(B)

Example 1
1 part of the compound represented by the formula (a) and 1 part of the compound represented by the formula (b) were dissolved by heating in a mixed solvent of 80 parts of 2-butoxyethanol and 20 parts of ethylene glycol. The obtained solution was filtered with a 0.45 μm membrane filter to obtain a solution of the composition for photo-alignment films. The solution of the composition for photo-alignment film thus obtained was applied onto a glass substrate with a spin coater, then heated on a hot plate at 80 ° C. for 2 minutes to evaporate the solvent, thereby obtaining a coating film. .

Using an ultra-high pressure mercury lamp as a light source, ultraviolet light near 365 nm obtained through a bandpass filter was converted into parallel light by a collimator mirror, and linearly polarized light having an irradiation intensity of 20 mW / cm ² was obtained through a polarizing filter. This polarized ultraviolet ray was irradiated perpendicularly to the coating film surface so as to have an energy of 1 J / cm ² . The coating film irradiated with ultraviolet rays was heated on a hot plate at 180 ° C. for 90 minutes.

  An epoxy thermosetting adhesive (trade name “XN5A”) containing silica beads having a diameter of 10 μm (trade name “HI-PRECICA” manufactured by Ube Nitto Kasei Co., Ltd.) around the glass substrate with a photo-alignment film prepared by the above method. ": Mitsui Chemicals Co., Ltd.)" was applied leaving only the liquid crystal injection port. After pre-curing at 80 ° C. for 30 minutes, it was pressure-bonded to a glass substrate not coated with an adhesive, and the adhesive was cured at 150 ° C. for 90 minutes. At this time, a liquid crystal cell was obtained by overlapping the liquid crystal alignment directions so as to be antiparallel. Subsequently, a liquid crystal composition A represented by the chemical formula (c) (Dainippon Ink Chemical Co., Ltd.) was injected and filled from a liquid crystal injection port under vacuum. The liquid crystal injection port was sealed with an epoxy photo-curing adhesive to obtain an antiparallel type (antiparallel type) liquid crystal element.

（ｃ）

(C)

For azimuth anchoring, a liquid crystal characteristic evaluation apparatus OMS-D12RD (manufactured by Chuo Seiki Co., Ltd.) was used. A chiral agent (spiral pitch 40 μm) was added to the liquid crystal composition A, which was injected into the liquid crystal cell, and the azimuth anchoring energy was determined from the difference in twist angle with the liquid crystal composition A not containing the chiral agent. The difference in the twist angle measured at this time is 0.1 ° or less, and as a result of calculation, the azimuth anchoring energy is 1 × 10 ⁻³ J / m ² or more, and the anchor is larger than a general rubbing alignment film. It was found to have ring energy.

Next, the optical stability of the photo-alignment film was tested. The test method is to irradiate polarized light (wavelength 365 nm) having a polarization plane in a direction different from the previously irradiated polarized light on the photo-alignment film after irradiation with polarized light and heating, and then the same method as described above A liquid crystal device was manufactured. The light durability was evaluated by observation using a polarizing plate for the presence or absence of a difference in the liquid crystal alignment state between what was irradiated with polarized light after heating and what was not. As a result, it was found that the photo-alignment film obtained by this method did not change its orientation direction even when irradiated with polarized ultraviolet rays of 5 J / cm ² after heating, and had excellent light durability.

(Example 2)
A liquid crystal device was prepared in the same manner as in Example 1 except that the liquid crystal composition B represented by the chemical formula (d) (Dainippon Ink Chemical Co., Ltd.) was used as the liquid crystal to be injected. And the light durability were evaluated. As a result, the azimuth anchoring energy is 1 × 10 −3 J / m ² or more, and the alignment direction of the liquid crystal by the alignment film does not change even when irradiated with polarized JV of 5 J / cm ^2. It was found to have durability.

（ｄ）

(D)

(Comparative Example 1)
1 part of an azo compound “Sudan IV” (manufactured by Tokyo Chemical Industry Co., Ltd.) represented by the formula (e) and 1 part of a compound represented by the formula (b) are dissolved in 98 parts of N, N-dimethylformamide, A liquid crystal element was produced in the same manner as in Example 1. As a result, although alignment of the liquid crystal was obtained, the azimuth anchoring energy was small and was 5 × 10 ⁻⁶ J / cm ² . On the other hand, when the light stability test was evaluated in the same manner as in Example 1, it was found that even when irradiated with polarized ultraviolet rays of 5 J / cm ² , the orientation direction did not change, and it had excellent light durability. It was.

（ｅ）

(E)

(Comparative Example 2)
Example 1 1 part of an azo compound represented by the formula (a) and 1 part of a tolan compound represented by the formula (f) were dissolved by heating in a mixed solvent of 80 parts of 2-butoxyethanol and 20 parts of ethylene glycol. A liquid crystal device was produced in the same manner as described above. When the azimuth anchoring energy of the obtained liquid crystal element was measured, it was 1.5 × 10 ⁻⁵ J / cm ² , which was a considerably small value compared to the rubbing alignment film. On the other hand, when the light stability test was evaluated in the same manner as in Example 1, it was found that the alignment state of the liquid crystal was changed by irradiating polarized ultraviolet rays of 5 J / cm ^{2 and} the durability against light was inferior. .

（ｆ）

(F)

(Comparative Example 3)
1 part of a polymerizable azo compound represented by formula (e) and 1 part of a tolan compound represented by formula (b) were dissolved by heating in a mixed solvent of 50 parts of N-methylpyrrolidone and 50 parts of 2-butoxyethanol. A liquid crystal cell was produced in the same manner as in Example 1.

（ｇ）

(G)

A liquid crystal composition A to which 0.2% of an anthraquinone derivative “M-137” (manufactured by Dainippon Ink & Chemicals, Inc.) was added was injected into the liquid crystal cell thus prepared in the same manner as in Example 1. An anti-parallel liquid crystal element was produced.
The order parameter was determined by measuring the absorbance of M-137 with respect to linearly polarized light having a wavelength of 625 nm using a polarized visible ultraviolet spectrophotometer, and calculating the order parameter using Equation (1).

(In the formula, A _// represents the absorbance when the alignment direction of the photo-alignment film is parallel to the vibration direction of the polarized light incident for measuring the absorbance, and A _⊥ represents the alignment direction of the photo-alignment film and the absorbance measurement. For this reason, it represents the absorbance when the vibration direction of the incident polarized light is perpendicular, where the larger the absolute value of the order parameter S, the higher the orientation of the liquid crystal.)
As a result, the order parameter of the liquid crystal element produced in this comparative example was 0.72, and it was found that the liquid crystal molecules showed good alignment.
Next, the azimuth anchoring energy was measured in the same manner as in Example 1. As a result, the azimuth anchoring energy was 1.3 × 10 ⁻⁴ J / m ² , which was smaller than that of a general rubbing alignment film.

(Comparative Example 4)
1 part of an azo compound represented by formula (a) and 1 part of a polymerizable compound having a biphenyl skeleton represented by formula (h) are heated and dissolved in a mixed solvent of 80 parts of 2-butoxyethanol and 20 parts of ethylene glycol. Then, a liquid crystal element was produced in the same manner as in Example 1.
Next, the azimuth anchoring energy was measured in the same manner as in Example 1. As a result, an azimuth anchoring energy of only 6.0 × 10 ⁻⁵ J / m ² was obtained.

（ｈ）

(H)

(Comparative Example 5)
2 parts of the azo compound represented by (a) was dissolved by heating in a mixed solvent of 80 parts of 2-butoxyethanol and 20 parts of ethylene glycol, and a liquid crystal device was produced in the same manner as in Example 1.
Next, the azimuth anchoring energy was measured in the same manner as in Example 1. As a result, an azimuth anchoring energy of only 1.1 × 10 ⁻⁴ J / m ² was obtained.

The photo-alignment film obtained by the present invention is suitably used for the purpose of aligning liquid crystals. For example, in a liquid crystal display device, two substrates having a photo-alignment film obtained in the present invention are bonded to each other with a surface having the photo-alignment film opposed to each other through a spacer, and a gap between the obtained liquid crystal cells is obtained. It is obtained by injecting liquid crystal into Moreover, an optical anisotropic body can be obtained by apply | coating a polymerizable liquid crystal composition on the photo-alignment film obtained by this invention, and making it harden | cure in the oriented state.

Claims (3)

A composition for photo-alignment films, comprising an azo compound represented by the general formula (1) and a polymerizable compound represented by the general formula (2).

(In General Formula (1), A ¹ and A ² are each independently a hydrogen atom, a halogen atom, a carboxy group, a halogenated methyl group, a halogenated methoxy group, a cyano group, a hydroxymethyl group, a hydroxyl group, —OR ^1. (However, R ¹ is an alkyl group having 2 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a C 1-6 carbon atom substituted with a lower alkoxy group having 1 to 6 carbon atoms. Represents a alkyl group), but the carboxy group may form a salt with an alkali metal.
A ³ and A ⁴ each independently represent a carboxy group, a sulfo group, an amino group, a hydroxy group, a carbamoyl group, a sulfamoyl group, or a methyloxycarbonyl group. However, the carboxy group and the sulfo group may form a salt with the alkali metal.
In General Formula (2), ^Xa and ^Xb each independently represent a hydrogen atom, a fluorine atom, a chlorine atom, or a methyl group, and l and m each represent an integer of 0 to 4. However, at least one of l and m is an integer of 1 or more. Z represents an aromatic hydrocarbon group or an alicyclic hydrocarbon group which may be substituted with one or more fluorine atoms, chlorine atoms or methyl groups. q and t each independently represent an integer of 1 to 20, and R ² and R ³ each independently represent a linear or branched divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms. Y ¹ and Y ² each independently represent a linking group selected from the group consisting of a single bond, —O—, —S—, —O—CO— or —CO—O—, and Q ¹ And Q ² are each independently acryloyloxy group, methacryloyloxy group, ClCH═CHCOO—, acrylamide group, methacrylamide group, ClCH═CHCONH—, vinyl group, CH ₂ ═CCl—, CHCl═CH—, epoxy Represents a reactive functional group selected from the group consisting of a group, an ethynyl group, a mercapto group, CH ₂ ═CHO— or a maleimide group. ) 2. The composition for a photoalignment film according to claim 1, wherein the content of the polymerizable compound represented by the general formula (2) is 10 to 70% by mass. After the composition for photo-alignment films according to claim 1 is applied on a substrate, in the manufacturing method of a photo-alignment film which irradiates light which has anisotropy to the coating film, light which has anisotropy was irradiated. Then, the manufacturing method of the photo-alignment film | membrane characterized by heating at 100-200 degreeC.