JP2014067038A - Optical anisotropic body - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an optical anisotropic body having excellent productivity and improved adhesiveness.SOLUTION: An optical anisotropic body is constituted by sequentially laminating at least base material made of organic material, a photo-alignment film and a polymer film of a polymerizable liquid crystal composition containing at least one polymerizable liquid crystalline compound. The optical anisotropic body has wetting tension of the base material, defined in JIS K6768, is larger than surface tension of a composition for the photo-alignment film used for forming the photo-alignment film. The optical anisotropic body is improved in adhesiveness, especially excellent in the adhesiveness when using plastic base material, thereby, is useful for components of a retardation film or an optical compensation sheet.

Description

The present invention relates to a polymerizable liquid crystal composition useful as a liquid crystal display element or an optical anisotropic body, and an optical material obtained by polymerizing a layer containing a polymerizable liquid crystal composition on a photo-alignment film and aligning the layers. Concerning an anisotropic body.

The polymerizable liquid crystal composition is useful as a component of an optical anisotropic body, and the optical anisotropic body is applied to various liquid crystal displays as an optical compensation sheet (retardation film), for example. The retardation film is obtained by applying a polymerizable liquid crystal composition to a substrate and curing the polymerizable liquid crystal composition by irradiating active energy rays in a state where the polymerizable liquid crystal composition is aligned by an alignment film or the like. It is done.

  On the other hand, in the case of producing a retardation film, that is, when a polymerizable liquid crystal layer is cured after forming an alignment film layer, if the alignment film layer is formed by a rubbing method, the apparatus is very large, Since there are problems such as easy generation and dust generation, a liquid crystal alignment film manufacturing technique that does not rub is attracting attention. In particular, the photo-alignment method for obtaining liquid crystal alignment by irradiating the coating film provided on the substrate with light having some anisotropy is expected to be practical because it is simple and can cope with an increase in size. .

  However, when a cured film of the polymerizable liquid crystal composition is formed on the photo-alignment film, there is a problem that the adhesive film at the interface between the alignment film and the cured film of the polymerizable liquid crystal composition is low, so that it is easy to peel off.

  In order to solve the above problems, improvements have been made mainly on the base material constituting the optical anisotropic body. For example, a method of improving the adhesiveness of an optical anisotropic body by a method of applying a silane coupling agent (Patent Document 1), an isocyanate compound (Patent Document 2), or the like to a substrate is known. However, any of these methods uses a so-called wet process in which a liquid composition such as a silane coupling agent or an isocyanate compound is applied to the base material, and the number of processes increases, and further processes such as a drying process and a heating process accompanying the application are performed. There was a problem of increasing. Therefore, an optical anisotropic body with improved adhesiveness that can be produced by a simpler dry process has been desired.

JP-A-2005-62424 JP-A-2005-274909

  The problem to be solved by the present invention is to provide an optical anisotropic body that is excellent in productivity, has high adhesion at the interface between the alignment film and the cured film of the polymerizable liquid crystal composition, and is difficult to peel off. Another object of the present invention is to provide a retardation film and an optical compensation sheet using the optical anisotropic body.

  As a means for improving the adhesion of the polymerizable liquid crystal composition containing the photo-alignment film and the polymerizable liquid crystal compound to the polymer film, the present inventors apply the wetting tension of the substrate made of an organic material to the photo-alignment film. The above problems have been solved by increasing the surface tension of the composition for photo-alignment films to be used and further setting the wetting tension of the substrate made of an organic material to a certain level or more.

  That is, the present invention provides an optical anisotropic body in which at least a base material made of an organic material, a photo-alignment film, and a polymer film of a polymerizable liquid crystal composition containing at least one polymerizable liquid crystal compound are sequentially laminated. The optical anisotropic body is characterized in that the wetting tension of the base material defined in JIS K6768 is larger than the surface tension of the composition for photo-alignment film used for the photo-alignment film.

  The optical anisotropic body of the present invention has high adhesion at the interface between the alignment film and the cured film of the polymerizable liquid crystal composition, and particularly excellent adhesion when a plastic substrate is used. It is useful as a structural member of a sheet.

The optical anisotropic body of the present invention is an optical material in which at least a base material made of an organic material, a photo-alignment film, and a polymer film of a polymerizable liquid crystal composition containing at least one polymerizable liquid crystal compound are sequentially laminated. It is an anisotropic body.
(Base material made of organic materials)
The base material used in the present invention is not particularly limited as long as it is a base material usually used for an optical anisotropic body, and is an organic material having heat resistance capable of withstanding heating at the time of manufacturing the optical anisotropic body. As such a substrate, cellulose derivatives, polyolefin, polyester, polyolefin, polycarbonate, polyacrylate, polyarylate, polyethersulfone, polyimide, polyphenylene sulfide, polyphenylene ether, nylon, polystyrene and the like can be used. Of these, polyester, polystyrene, polyolefin, cellulose derivative, polyarylate, and polycarbonate are preferable.

  Moreover, it is preferable to perform a surface treatment in order to obtain a substrate used in the present invention, and the wetting tension of the obtained substrate is a composition for a photoalignment film used for a photoalignment film laminated on the substrate. It is more preferable that the surface tension is greater than the surface tension, and the specific wetting tension is preferably 40 to 65 mN / m. The wetting tension used in the present invention is defined by JIS K6768 (plastic-film and sheet-wetting tension test).

Examples of the surface treatment method for the substrate include simple and dry corona treatment, plasma treatment, UV treatment, and ozone treatment.
In the corona treatment, high-energy electrons and ions collide with the substrate surface by corona discharge to generate radicals and ions. Ambient ozone, oxygen, nitrogen, moisture and the like react with these to introduce polar functional groups such as a carbonyl group, a carboxyl group, and a hydroxyl group on the substrate surface. In the case of plasma treatment, polar functional groups are introduced to the substrate surface by arc discharge rather than corona discharge. In the UV treatment, molecules on the substrate surface are excited by ultraviolet rays, and photoreaction and photolysis occur, whereby the substrate surface is altered. In the case of ozone treatment, ozone is usually generated by ultraviolet rays having a short wavelength, and polar functional groups are introduced onto the substrate surface in the same manner as in the corona treatment.

In UV treatment, ultraviolet rays of 254 nm or 313 nm are generally used, and a high pressure mercury lamp, an ultrahigh pressure mercury lamp, or the like is used as a light source. When ultraviolet light of 240 nm or less is used, oxygen is decomposed and ozone is generated. In the above case, a low-pressure mercury lamp or a xenon excimer lamp is used as the light source.
These treatments may be used in combination with each other, but it is preferable to carry out treatment that combines UV treatment and ozone treatment.

  The optical anisotropic body of the present invention comprises a substrate made of an organic material, a photo-alignment film, and a polymer film of a polymerizable liquid crystal composition containing at least one polymerizable liquid crystal compound. Since the photo-alignment film is very thin as compared with the film, it is considered that the surface state of the base material affected the polymer film.

When performing the surface treatment of the base material, if the base material is too close to the discharge part or the ultraviolet ray generation part, not only the surface treatment but also decomposition of the organic material inside the base material may occur. In general, the processing is performed with Since the distance greatly depends on the performance of each apparatus, it is necessary to match the processing apparatus to be used.
Examples of the method for measuring the wetting tension of the substrate obtained by performing the surface treatment include a contact angle measurement method, a wetting reagent method, a plate method, and a ring method, but the wetting reagent method defined in JIS K6768 is very It is simple and preferable.

(Photo-alignment film)
As the photo-alignment film used in the present invention, a known and commonly used photo-alignment compound can be used. Specifically, a coumarin compound, a chalcone compound, a cinnamate compound, a fulgide compound, an anthraquinone compound, an azo compound, and an arylethene compound. And the like, and a compound that undergoes photoisomerization or photodimerization is exemplified, and an azo compound is particularly preferable.

(Polymerizable liquid crystal compound)
The polymerizable liquid crystal composition constituting the optical anisotropic body of the present invention includes a polymerizable liquid crystal composition containing two or more kinds of rod-like polymerizable liquid crystal compounds having at least two polymerizable functional groups, and at least two or more polymerizable liquid crystal compounds. Rod-like polymerizable liquid crystal compound having polymerizable functional group, polymerizable liquid crystal composition containing rod-like polymerizable liquid crystal compound having one polymerizable functional group, and discotic liquid crystal having at least one polymerizable functional group A polymerizable liquid crystal composition containing two or more kinds of compounds and a polymerizable liquid crystal composition containing two or more kinds of banana-type liquid crystal compounds having at least one polymerizable functional group are preferred.
The polymerizable liquid crystal compound contained in the polymerizable liquid crystal composition used in the present invention is not particularly limited and can be used. As the polymerizable liquid crystal compound, a rod-like polymerizable liquid crystal compound or a disk-like polymerizable liquid crystal compound is preferably used, and a rod-like polymerizable liquid crystal compound is particularly preferred.
The rod-like polymerizable liquid crystal compound has the general formula (1)

(Wherein P represents a reactive functional group, Sp represents a spacer group having 1 to 20 carbon atoms, m represents 0 or 1, MG represents a mesogenic group or a mesogenic support group, and R ¹ represents Represents a halogen atom, a cyano group or an alkyl group having 1 to 25 carbon atoms, and the alkyl group may be substituted by one or more halogen atoms or CN, and one CH ₂ present in the group. Group or two or more non-adjacent CH ₂ groups are each independently of each other such that —O—, —S—, —NH—, —N (CH ₃ ) -, -CO-, -COO-, -OCO-, -OCOO-, -SCO-, -COS- or -C≡C- may be substituted, or R ¹ may be represented by the general formula (1-a)

（式中、Pは反応性官能基を表し、Spは炭素原子数１〜２０のスペーサー基を表し、mは０又は１を表す。）で表される構造を表す。）で表される化合物を含有することが好ましく、一般式（１）において、Spがアルキレン基を表し、（該アルキレン基は１つ以上のハロゲン原子又はCNにより置換されていても良く、この基中に存在する１つのCH₂基又は隣接していない２つ以上のCH₂基はそれぞれ相互に独立して、酸素原子が相互に直接結合しない形で、-O-、-S-、-NH-、-N(CH₃)-、-CO-、-COO-、-OCO-、-OCOO-、-SCO-、-COS-又は-C≡C-により置き換えられていても良い。）MGが一般式（１-b）

(Wherein P represents a reactive functional group, Sp represents a spacer group having 1 to 20 carbon atoms, and m represents 0 or 1). In general formula (1), Sp represents an alkylene group, and the alkylene group may be substituted with one or more halogen atoms or CN. independently one CH ₂ group or adjacent to each other each of the two or more CH ₂ groups not present in the form in which the oxygen atoms are not directly bonded to one another, -O -, - S -, - NH -, -N (CH ₃ )-, -CO-, -COO-, -OCO-, -OCOO-, -SCO-, -COS- or -C≡C- may be substituted.) General formula (1-b)

(In the formula, A1, A2 and A3 are each independently 1,4-phenylene group, 1,4-cyclohexylene group, 1,4-cyclohexenyl group, tetrahydropyran-2,5-diyl group, 1, 3-dioxane-2,5-diyl group, tetrahydrothiopyran-2,5-diyl group, 1,4-bicyclo (2,2,2) octylene group, decahydronaphthalene-2,6-diyl group, pyridine- 2,5-diyl group, pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 2,6-naphthylene group, Phenanthrene-2,7-diyl group, 9,10-dihydrophenanthrene-2,7-diyl group, 1,2,3,4,4a, 9,10a-octahydrophenanthrene 2,7-diyl group or fluorene 2, Represents a 7-diyl group, the 1,4-phenylene group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 2,6-naphthylene group, phenanthrene-2,7-diyl group, 9 , 10-Dihydrophenanthrene-2,7-diyl group 1,2,3,4,4a, 9,10a- octahydrophenanthrene 2,7-diyl group and fluorene 2,7-diyl group is 1 or more F as _{substituents, Cl, CF 3, OCF 3} , cyano Group, an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkanoyl group, an alkanoyloxy group, an alkenyl group having 2 to 8 carbon atoms, an alkenyloxy group, an alkenoyl group or an alkenoyloxy group. , Z0, Z1, Z2 and Z3 are each independently -COO-, -OCO-, -CH ₂ CH _2- , -OCH _2- , -CH ₂ O-, -CH = CH-, -C≡C -, -CH = CHCOO-, -OCOCH = CH-, -CH ₂ CH ₂ COO-, -CH ₂ CH ₂ OCO-, -COO CH ₂ CH _2- , -OCOCH ₂ CH _2- , -CONH-,- NHCO- or a single bond, n represents 0, 1 or 2), and P represents a general formula (1-c), general formula (1-d) and general formula (1- e)

(In the formula, R ²¹ , R ²² , R ²³ , R ³¹ , R ³² , R ³³ , R ⁴¹ , R ⁴² and R ⁴³ are each independently a hydrogen atom, a halogen atom or an alkyl group having 1 to 5 carbon atoms. And n represents 0 or 1. It is more preferable to contain a compound represented by a substituent selected from the group consisting of substituents represented by:
Here, as a compound contained in the polymerizable liquid crystal composition, more specifically, the general formula (2)

Wherein m represents 0 or 1, W ¹ and W ² each independently represent a single bond, —O—, —COO— or —OCO—, and Y ¹ and Y ² each independently represent — COO- or -OCO- is represented, and r and s each independently represent an integer of 2 to 18, the 1,4-phenylene group present in the formula is an alkyl group or alkoxy group having 1 to 7 carbon atoms , An alkanoyl group, a cyano group, or a halogen atom may be substituted, which is preferable because an optically anisotropic body excellent in mechanical strength and heat resistance can be obtained.
The general formula (3)

(In the formula, Z ¹ represents a hydrogen atom, a halogen atom, a cyano group or a hydrocarbon group having 1 to 20 carbon atoms, Z ² represents a hydrogen atom or a methyl group, t represents 0 or 1, A, B and C are each independently a 1,4-phenylene group, a 1,4-phenylene group in which a non-adjacent CH group is substituted with nitrogen, a 1,4-cyclohexylene group, one or two non-adjacent CH ₂ Represents a 1,4-cyclohexylene group or 1,4-cyclohexenylene group in which the group is substituted with an oxygen or sulfur atom, and the 1,4-phenylene group present in the formula is an alkyl having 1 to 7 carbon atoms Group, an alkoxy group, an alkanoyl group, a cyano group or a halogen atom, and Y ³ and Y ⁴ are each independently a single bond, —CH ₂ CH ₂ —, —CH ₂ O—, _{-OCH 2 -, - COO -,} - OCO -, - C≡C -, - CH = CH -, - CF = CF -, - (CH 2) 4 -, - CH 2 CH 2 CH 2 O -, - OCH ₂ CH ₂ CH _2- , -CH = CHCH ₂ CH _2- , -CH _{2 CH 2 CH = CH -, -} CH = CHCOO -, - OCOCH = CH -, - CH 2 CH 2 COO -, - CH 2 CH 2 OCO -, - COO CH 2 CH 2 - or -OCOCH ₂ CH ₂ - and Y ⁵ represents a single bond, —O—, —COO—, —OCO—, or —CH═CHCOO—)), the viscosity of the polymerizable liquid crystal composition can be reduced and the liquid crystal temperature range can be reduced. Is preferable because it can be reduced to room temperature or near room temperature.
Moreover, general formula (4)

(In the formula, Z ³ represents a hydrogen atom, a halogen atom, a cyano group, a hydrocarbon group having 1 to 20 carbon atoms, Z ⁴ represents a hydrogen atom or a methyl group, and W ³ each independently represents a single bond,- O—, —COO—, —OCO—, v represents an integer of 2 to 18, u represents an integer of 0 or 1, and D, E, and F are each independently a 1,4-phenylene group. 1,4-phenylene group in which non-adjacent CH groups are substituted with nitrogen, 1,4-cyclohexylene group, 1,4-cyclohexene group in which one or two non-adjacent CH ₂ groups are substituted with oxygen or sulfur atoms Represents a silene group or a 1,4-cyclohexenylene group, and these D, E, and F are one or more alkyl groups, alkoxy groups, alkanoyl groups, cyano groups, or halogen atoms having 1 to 7 carbon atoms. Y ⁶ and Y ⁷ may each independently be a single bond, —CH ₂ CH ₂ —, —CH ₂ O—, —OCH ₂ —, —COO—, —OCO—, —C≡C -, -CH = C H -, - CF = CF - , - (CH 2) 4 -, - CH 2 CH 2 CH 2 O -, - OCH 2 CH 2 CH 2 -, - CH = CHCH 2 CH 2 -, - CH 2 CH 2 CH = CH -, - CH = CHCOO -, - OCOCH = CH -, - CH 2 CH 2 COO -, - CH 2 CH 2 OCO -, - COOCH 2 CH 2 - or -OCOCH ₂ CH ₂ -, Y represents ⁸ represents a single bond, —O—, —COO—, —OCO—, or —CH═CHCOO—.) When the compound represented by It is preferable because the physical properties can be adjusted.
Specific examples of the compound represented by the general formula (1) can be given below.

（式中、j及びkはそれぞれ独立的に２〜１８の整数を表す。）
又、一般式（２）で表される化合物の具体例を以下に挙げることができる。

(Wherein j and k each independently represents an integer of 2 to 18)
Specific examples of the compound represented by the general formula (2) can be given below.

（式中、j及びkはそれぞれ独立的に２〜１８の整数を表す。）
又、一般式（３）で表される化合物の具体的な例として、化合物の構造と相転移温度を以下に挙げることができる。

(Wherein j and k each independently represents an integer of 2 to 18)
As specific examples of the compound represented by the general formula (3), the structure of the compound and the phase transition temperature can be listed below.

(In the formula, a cyclohexane ring represents a transcyclohexane ring, a number represents a phase transition temperature, C represents a crystalline phase, N represents a nematic phase, S represents a smectic phase, and I represents an isotropic liquid phase.)
Specific examples of the compound represented by the general formula (4) can be given below.

(In the formula, X ¹ represents a hydrogen atom or a methyl group, and R represents an alkyl group having 1 to 20 carbon atoms.)
The discotic liquid crystal compound having a polymerizable group used in the present invention has a benzene derivative, a triphenylene derivative, a truxene derivative, a phthalocyanine derivative or a cyclohexane derivative as a mother nucleus at the center of the molecule, a linear alkyl group, a linear It preferably has a structure in which an alkoxy group or a substituted benzoyloxy group is radially substituted as its side chain.

（式中、R⁵はそれぞれ独立して一般式（５-ａ）で表される置換基を表す。）

(In the formula, each R ⁵ independently represents a substituent represented by the general formula (5-a).)

(In the formula, R ⁶ and R ⁷ each independently represent a hydrogen atom, a halogen atom or a methyl group, and R ⁸ represents an alkoxy group having 1 to 20 carbon atoms, and the hydrogen atom in the alkoxy group represents a general formula. (It may be substituted with a substituent represented by (5-b), general formula (5-c) or general formula (5-d)).

Wherein R ⁸¹ , R ⁸² , R ⁸³ , R ⁸⁴ , R ⁸⁵ , R ⁸⁶ , R ⁸⁷ , R ⁸⁸ and R ⁸⁹ are each independently a hydrogen atom, a halogen atom or an alkyl group having 1 to 5 carbon atoms. And n represents 0 or 1). In general formula (5), at least one of R ⁸ is represented by general formula (5-b) or general formula (5). -c) or an alkoxy group substituted by a substituent represented by the general formula (5-d), preferably all of R ⁸ are represented by the general formula (5-b), the general formula (5-c) or It is particularly preferable to represent an alkoxy group substituted by a substituent represented by the general formula (5-d).
Furthermore, the general formula (5-a) specifically represents the general formula (5-e).

（式中nは２〜９の整数を表す。）で表される構造を有することが特に好ましい。
また、本発明で用いられる重合性基を有するバナナ型液晶化合物は、一般式（６）

It is particularly preferable to have a structure represented by the formula (wherein n represents an integer of 2 to 9).
The banana-type liquid crystal compound having a polymerizable group used in the present invention has the general formula (6)

(In the formula, P represents a reactive functional group, Sp represents a spacer group having 1 to 20 carbon atoms, m represents 0 or 1, MG ¹ and MG ² represent a mesogenic group or a mesogenic supporting group. , BA is a divalent cyclic group that imparts a bent structure to the compound, and R ⁹ represents a halogen atom, a cyano group, or an alkyl group having 1 to 25 carbon atoms, and the alkyl group is one or more halogen atoms. or may be substituted by CN, independently the one CH ₂ group present in the group or each of two or more _non-adjacent CH ₂ groups to each other, form the oxygen atoms are not directly bonded to each other -O-, -S-, -NH-, -N (CH ₃ )-, -CO-, -COO-, -OCO-, -OCOO-, -SCO-, -COS- or -C≡C May be replaced by-or R ⁹ may be represented by the general formula (6-a)

(Wherein P represents a reactive functional group, Sp represents a spacer group having 1 to 20 carbon atoms, and n represents 0 or 1). In the general formula (6), Sp represents an alkylene group, and the alkylene group may be substituted with one or more halogen atoms or CN. independently one CH ₂ group or adjacent to each other each of the two or more CH ₂ groups not present in the form in which the oxygen atoms are not directly bonded to one another, -O -, - S -, - NH -, -N (CH ₃ )-, -CO-, -COO-, -OCO-, -OCOO-, -SCO-, -COS- or -C≡C- may be substituted.) MG1, MG2 is the general formula (6-b)

(In the formula, A1, A2 and A3 are each independently 1,4-phenylene group, 1,4-cyclohexylene group, 1,4-cyclohexenyl group, tetrahydropyran-2,5-diyl group, 1, 3-dioxane-2,5-diyl group, tetrahydrothiopyran-2,5-diyl group, 1,4-bicyclo (2,2,2) octylene group, decahydronaphthalene-2,6-diyl group, pyridine- 2,5-diyl group, pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 2,6-naphthylene group, Phenanthrene-2,7-diyl group, 9,10-dihydrophenanthrene-2,7-diyl group, 1,2,3,4,4a, 9,10a-octahydrophenanthrene 2,7-diyl group or fluorene 2, Represents a 7-diyl group, the 1,4-phenylene group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 2,6-naphthylene group, phenanthrene-2,7-diyl group, 9 , 10-Dihydrophenanthrene-2,7-diyl group 1,2,3,4,4a, 9,10a- octahydrophenanthrene 2,7-diyl group and fluorene 2,7-diyl group is 1 or more F as _{substituents, Cl, CF 3, OCF 3} , cyano Group, an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkanoyl group, an alkanoyloxy group, an alkenyl group having 2 to 8 carbon atoms, an alkenyloxy group, an alkenoyl group or an alkenoyloxy group. , Z0, Z1, Z2 and Z3 are each independently -COO-, -OCO-, -CH ₂ CH _2- , -OCH _2- , -CH ₂ O-, -CH = CH-, -C≡C -, -CH = CHCOO-, -OCOCH = CH-, -CH ₂ CH ₂ COO-, -CH ₂ CH ₂ OCO-, -COO CH ₂ CH _2- , -OCOCH ₂ CH _2- , -CONH-,- NHCO- or a single bond, l represents 0, 1 or 2), and P represents a general formula (6-c), general formula (6-d) and general formula (6- e)

（式中、R⁹¹、R⁹²、R⁹³、R⁹⁴、R⁹⁵、R⁹⁶、R⁹⁷、R⁹⁸及びR⁹⁹はそれぞれ独立的に水素原子、ハロゲン原子又は炭素原子数１〜５のアルキル基を表し、nは０又は１を表す。）で表される置換基からなる群より選ばれる置換基で表される化合物を含有することが好ましい。

(Wherein R ⁹¹ , R ⁹² , R ⁹³ , R ⁹⁴ , R ⁹⁵ , R ⁹⁶ , R ⁹⁷ , R ⁹⁸ and R ⁹⁹ are each independently a hydrogen atom, a halogen atom or an alkyl group having 1 to 5 carbon atoms. And n represents 0 or 1. It is preferable to contain a compound represented by a substituent selected from the group consisting of substituents represented by:

(Polymerization initiator)
In general, the polymerizable liquid crystal composition of the present invention is polymerized by irradiation with light such as ultraviolet rays or heating. As the photopolymerization initiator used in the case of carrying out by light irradiation, known and conventional ones can be used, for example, 2-hydroxy-2-methyl-1-phenylpropan-1-one (“Darocur 1173” manufactured by Merck), 1 -Hydroxycyclohexyl phenyl ketone ("Irgacure 184" manufactured by Ciba Specialty Chemicals), 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one ("Darocur 1116" manufactured by Merck), 2-Methyl-1-[(methylthio) phenyl] -2-morpholinopropane-1 (“Irgacure 907” manufactured by Ciba Specialty Chemicals). Benzylmethylketal ("Irgacure 651" manufactured by Ciba Specialty Chemicals). A mixture of 2,4-diethylthioxanthone (“Kayacure DETX” manufactured by Nippon Kayaku Co., Ltd.) and ethyl p-dimethylaminobenzoate (“Kayacure EPA” manufactured by Nippon Kayaku Co., Ltd.) -ITX ") and a mixture of ethyl p-dimethylaminobenzoate, acylphosphine oxide (" Lucirin TPO "manufactured by BASF), and the like. The amount of the photopolymerization initiator used is preferably 10% by mass or less, particularly preferably 0.5 to 5% by mass with respect to the polymerizable liquid crystal compound.

  In addition, as the thermal polymerization initiator used in the thermal polymerization, known and conventional ones can be used, for example, methyl acetoacetate peroxide, cumene hydroperoxide, benzoyl peroxide, bis (4-t-butylcyclohexyl). Peroxydicarbonate, t-butylperoxybenzoate, methyl ethyl ketone peroxide, 1,1-bis (t-hexylperoxy) 3,3,5-trimethylcyclohexane, p-pentahydroperoxide, t-butylhydro Organic peroxides such as peroxide, dicumyl peroxide, isobutyl peroxide, di (3-methyl-3-methoxybutyl) peroxydicarbonate, 1,1-bis (t-butylperoxy) cyclohexane, 2, 2'-azobisisobutyronitrile Azonitrile compounds such as 2,2′-azobis (2,4-dimethylvaleronitrile), azoamidine compounds such as 2,2′-azobis (2-methyl-N-phenylpropion-amidine) dihydrochloride, 2,2 ′ Azoamide compounds such as azobis {2-methyl-N- [1,1-bis (hydroxymethyl) -2-hydroxyethyl] propionamide} and alkylazo such as 2,2′azobis (2,4,4-trimethylpentane) Compounds and the like can be used. The amount of the thermal polymerization initiator used is preferably 10% by mass or less, particularly preferably 0.5 to 5% by mass with respect to the polymerizable liquid crystal compound.

(solvent)
The solvent used in the present invention is not particularly limited as long as it is a solvent that can dissolve a part of a base material made of an organic material, but the polymerizable liquid crystal compound exhibits good solubility. Can be used. For example, aromatic hydrocarbons such as toluene, xylene, cumene and mesitylene, ester solvents such as methyl acetate, ethyl acetate, propyl acetate and butyl acetate, ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone, tetrahydrofuran, 1 , 2-dimethoxyethane, ether solvents such as anisole, amide solvents such as N, N-dimethylformamide, N-methyl-2-pyrrolidone, propylene glycol monomethyl ether acetate, diethylene glycol monomethyl ether acetate, γ-butyrolactone, chlorobenzene Etc. These can be used alone or in combination of two or more.
The ratio of the solvent is not particularly limited as long as the polymerizable liquid crystal composition used in the present invention is usually applied by coating, so long as the applied state is not significantly impaired, but the solid content of the polymerizable liquid crystal composition and the solvent The ratio is preferably 0.1: 99.9 to 80:20, and more preferably 1:99 to 50:50 in view of applicability.

(Other ingredients)
In the polymerizable liquid crystal composition of the present invention, a liquid crystal compound having no polymerizable group may be added as necessary. However, if the addition amount is too large, the liquid crystal compound may be eluted from the obtained optical anisotropic body to contaminate the laminated member, and in addition, the heat resistance of the optical anisotropic body may be reduced. In this case, the content is preferably 30% by mass or less, more preferably 15% by mass or less, and particularly preferably 5% by mass or less with respect to the total amount of the polymerizable liquid crystal compound.

  The polymerizable liquid crystal composition used in the present invention may be added with a compound having a polymerizable group but not a polymerizable liquid crystal compound. Such a compound can be used without particular limitation as long as it is generally recognized as a polymerizable monomer or polymerizable oligomer in this technical field. When adding, it is preferable that it is 10 mass% or less with respect to the polymeric liquid crystal composition of this invention, and 3 mass% or less is still more preferable.

The polymerizable liquid crystal composition used in the present invention may be added with a compound having optical activity, that is, a chiral compound. The chiral compound itself does not need to exhibit a liquid crystal phase, and may or may not have a polymerizable group. Moreover, the direction of the spiral of the chiral compound can be appropriately selected depending on the intended use of the polymer.
Specifically, for example, CB-15, “C-15”, Merck manufactured by BDH Corporation having cholesterol as a chiral group having cholesteryl group as cholesterol group, cholesterol stearate, and 2-methylbutyl group as a chiral group. “S-1082” manufactured by the company, “CM-19”, “CM-20”, “CM” manufactured by Chisso, “S-811” manufactured by Merck having 1-methylheptyl group as a chiral group, “CM-21”, “CM-22” and the like manufactured by the company can be mentioned. A chiral compound having a polymerizable group can also be used.

When adding a chiral compound, depending on the use of the polymer of the polymerizable liquid crystal composition of the present invention, the value obtained by dividing the thickness (d) of the obtained polymer by the helical pitch (P) in the polymer (d / P) is preferably added in an amount in the range of 0.1 to 100, more preferably in the range of 0.1 to 20.
In order to uniformly apply the polymerizable liquid crystal composition used in the present invention and obtain a photo-alignment film having a uniform film thickness, a general-purpose additive can be used. For example, additives such as a leveling agent, a thixotropic agent, a surfactant, an ultraviolet absorber, an infrared absorber, an antioxidant, and a surface treatment agent can be added to such an extent that the liquid crystal alignment ability is not significantly reduced.

(Photo-alignment film)
As the photo-alignment film used in the present invention, a known and commonly used photo-alignment compound can be used. Specifically, coumarin compounds, chalcone compounds, cinnamate compounds, fulgide compounds, anthraquinone compounds, azo compounds, arylethene compounds. And the like, and a compound that undergoes photoisomerization or photodimerization is exemplified, and an azo compound is particularly preferable.
More specifically, the azo compound contains an azo compound represented by the general formula (7).

In general formula (7), R ¹ and R ² are each independently a hydroxy group, (meth) acryloyl group, (meth) acryloyloxy group, (meth) acrylamide group, vinyl group, vinyloxy group and maleimide group. Represents a polymerizable functional group selected from the group consisting of R ¹ and R ² preferably represent a hydroxy group, but when importance is attached to light and heat stability, it is preferable that R ¹ and R ² represent a polymerizable functional group. Then, a (meth) acryloyloxy group is particularly preferable. A maleimide group is more preferable because a polymerization initiator is not required.

m and n each independently represents an integer of 0 to 4, but when R ¹ represents a hydroxy group, m preferably represents 0, and when R ² represents a hydroxy group, n preferably represents 0. . On the other hand, when R ¹ is a polymerizable functional group, m preferably represents an integer of 1 to 4, and when R ² is a polymerizable functional group, n preferably represents an integer of 1 to 4.

A ¹ and A ² each independently represents a single bond or a divalent hydrocarbon group. Examples of the divalent hydrocarbon group include a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, A linear alkylene group having 1 to 18 carbon atoms such as hexamethylene group, heptamethylene group, octamethylene group, nonamethylene group, decamethylene group, undecamethylene group, dodecamethylene group; 1-methylethylene group, 1-methyltrimethyl group 1 to 1 carbon atoms such as ethylene group, 2-methyltriethylene group, 1-methyltetraethylene group, 2-methyltetraethylene group, 1-methylpentamethylene group, 2-methylpentamethylene group, 3-methylpentamethylene group 18 branched alkylene groups; phenylene groups such as p-phenylene group; 2-methoxy-1,4-phenylene group, 3-methoxy-1 , 4-phenylene group, 2-ethoxy-1,4-phenylene group, 3-ethoxy-1,4-phenylene group, 2,3,5-trimethoxy-1,4-phenylene group and the like. Examples thereof include a phenylene group having a linear or branched alkoxy group; and an arylene group such as a 2,6-naphthalenediyl group.

R ^{3 to} R ⁶ are each independently a hydrogen atom, a halogen atom, a halogenated alkyl group, an allyloxy group, a cyano group, a nitro group, an alkyl group, a hydroxyalkyl group, an alkoxy group, a carboxy group or an alkali metal salt thereof, an alkoxy Carbonyl group, halogenated methoxy group, hydroxy group, sulfo group or alkali metal salt thereof, amino group, carbamoyl group, sulfamoyl group or (meth) acryloyl group, (meth) acryloyloxy group, (meth) acryloylamino group, vinyl group Represents a polymerizable functional group selected from the group consisting of a vinyloxy group and a maleimide group.

  Examples of the halogen atom include a fluorine atom and a chlorine atom. Examples of the halogenated alkyl group include a trichloromethyl group and a trifluoromethyl group. Examples of the halogenated methoxy group include a chloromethoxy group and a trifluoromethoxy group.

  As the alkoxy group, the alkyl group portion is substituted with a lower alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a lower alkoxy group having 1 to 6 carbon atoms. -6 lower alkyl groups. Examples of the lower alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, and a 1-methylethyl group. Examples of the lower alkyl group having 1 to 6 carbon atoms substituted with a lower alkoxy group having 1 to 6 carbon atoms include a methoxymethyl group, 1-ethoxyethyl group, tetrahydropyranyl group and the like.

Examples of the hydroxyalkyl group include a hydroxyalkyl group having 1 to 4 carbon atoms, specifically, a hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group. Group, 3-hydroxypropyl group, 1-hydroxybutyl group and the like.
Examples of the carbamoyl group include those having an alkyl group portion of 1 to 6 carbon atoms, such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, and a 1-methylethyl group.

  Among these, a halogen atom, a carboxy group, a halogenated methyl group, a halogenated methoxy group, a methoxy group, an ethoxy group, a propoxy group, a hydroxymethyl group, a carbamoyl group, a dimethylcarbamoyl group or a cyano group are preferable, and a carboxy group, hydroxymethyl A group or a trifluoromethyl group is particularly preferred in that good orientation can be obtained.

Further, when R ³ and R ⁴ are substituted at the meta positions of the phenylene group at both ends of the 4,4′-bis (phenylazo) biphenyl skeleton, an excellent photo-alignment film is obtained, and R ⁵ and R ⁶ are , 4,4′-bis (phenylazo) biphenyl skeleton is preferably substituted at the 2,2′-position, and thus excellent photo-alignment properties can be obtained.
Specifically, the azo compound represented by the general formula (7) is preferably an azo compound having the following structure.

The compound represented by the general formula (7) shows high solubility in water or a polar organic solvent, and after being applied to the substrate, it is uniform on the substrate simply by removing the water or polar organic solvent. In addition, a stable photo-alignment film can be formed. Moreover, the compound represented by General formula (7) can also be used independently, and 2 or more types of compounds can also be mixed and used for it.
((Meth) acrylate having hydrophilic group)
Examples of the hydrophilic group of the (meth) acrylate having a hydrophilic group used in the present invention include a hydroxyl group, a carboxyl group, a sulfo group, and an amino group, and a (meth) acrylate having a hydroxyl group or a carboxyl group is generally used. It is preferable from the viewpoint of miscibility with the compound represented by formula (1). The number of (meth) acryloyl groups per molecule is not particularly limited, and may be one or two or more.

As the (meth) acrylate having a hydroxyl group, those having two or more hydroxyl groups are particularly preferred because of their high hydrophilicity. Specifically, monovalent epoxy (meth) acrylates such as glycidyl (meth) acrylate; propylene glycol, butanediol, pentanediol, hexanediol, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol, tetraethylene glycol Diglycidyl ether of dihydric alcohols such as polyethylene glycol, polypropylene glycol, neopentyl glycol, neopentyl glycol hydroxypivalate, bisphenol A, ethoxylated bisphenol A; trimethylolpropane, ethoxylated trimethylolpropane, propoxylated trimethylol Epoxy compounds such as triglycidyl ethers of trihydric alcohols such as propane and glycerin (meth) acrylate Epoxy acrylate compounds, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, glycerol di (meth) acrylate, trimethylolpropane di (meth) acrylate and ditrimethylolpropane tri ( (Meth) acrylates, and those derived from epoxy resins and carboxylic acids, (meth) acrylic acid adducts of glycidyl (meth) acrylate,
Trimethylolpropane di (meth) acrylate, ethoxylated trimethylolpropane di (meth) acrylate, propoxylated trimethylolpropane di (meth) acrylate, tris 2-hydroxyethyl isocyanurate di (meth) acrylate, glycerin di (meth) acrylate An alcoholic di (meth) acrylate having a hydroxyl residue, such as

Pentaerythritol di (meth) acrylate, dipentaerythritol di (meth) acrylate, ditrimethylolpropane di (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol tri (meth) acrylate, ditrimethylolpropane tri (meth) Alcoholic polyfunctional compounds having a hydroxyl residue such as acrylate, dipentaerythritol tetra (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, ditrimethylolpropane hexa (meth) acrylate ( (Meth) acrylate,

  Hydrogenation of (meth) acrylates and aromatic epoxy acrylates obtained by adding (meth) acrylic acid to an epoxy compound such as polyglycidyl ether of polyhydric phenol having at least one aromatic ring or its alkylene oxide adduct Examples of the type include alicyclic epoxy acrylate. In addition, as polyhydric phenol here, bisphenol compounds, such as bisphenol A, bisphenol F, bisphenol S, the alkylene oxide adduct of a bisphenol compound, a phenol novolak, a cresol novolak, etc. can be used.

  Since the (meth) acrylate having a carboxyl group has sufficiently high hydrophilicity of the carboxyl group, the number of carboxyl groups per molecule is not particularly limited, and may be one or two or more. However, as the number of carboxyl groups increases, the solubility in the solvent deteriorates and the crystallinity of the compound also increases. Therefore, it is preferable that the number of carboxyl groups is small as long as the resistance to the adhesive member or the solvent does not deteriorate. In particular, in the case of a compound having a carboxyl group directly connected to an aromatic ring, the number of carboxyl groups per molecule is particularly preferably 2 or less.

  Specifically, for example, 2- (meth) acryloyloxyethyl hexahydrophthalate, 2-acryloyloxyethyl phthalate, 2-methacryloyloxyethyl phthalate, EO-modified succinic acid acrylate, etc., at least one in a molecule and one molecule A compound obtained by adding an acid anhydride such as phthalic anhydride to a hydroxyl group-containing vinyl monomer such as the above-mentioned (meth) acryloyl group, 2-hydroxyethyl (meth) acrylate, Examples include benzoic acid derivatives substituted with an alkyl (oxy) group into which a (meth) acryloyloxy group has been introduced. Although the number of substituents may be one or more, the number of substituents is preferably 1 to 3 from the viewpoint of ease of synthesis. In addition, when a plurality of substituents are introduced, it is preferable to select a position that lowers the symmetry of the molecule as the position to be substituted from the viewpoint that the crystallinity is not excessively increased. Specifically, 2- (ω- (meth) acryloyloxyalkyl (oxy)) benzoic acid, 2,3-di (ω- (meth) acryloyloxyalkyl (oxy)) benzoic acid, 2,4-di ( ω- (meth) acryloyloxyalkyl (oxy)) benzoic acid, 2,5-di (ω- (meth) acryloyloxyalkyl (oxy)) benzoic acid, 3- (ω- (meth) acryloyloxyalkyl (oxy)) ) Benzoic acid, 3,4-di (ω- (meth) acryloyloxyalkyl (oxy)) benzoic acid, 4- (ω- (meth) acryloyloxyalkyl (oxy)) benzoic acid, of the methylene group of the alkyl chain The thing of a number 1-14 is mentioned. Particularly preferred are those having 2 to 10 methylene groups.

  Examples of commercially available photopolymerizable compounds having a carboxy group and at least one (meth) acryloyl group in one molecule include, for example, trade names “Light Acrylate HOAHH” and “Light Acrylate HOHH” manufactured by Kyoeisha Oil Chemical Co., Ltd. , “Light acrylate HOMPL”, “light acrylate HOMPP”, “light acrylate HOA-MS”, and the like.

The (meth) acrylate having a hydrophilic group may be used alone or in combination of two or more.
Moreover, since the (meth) acrylate having a hydrophilic group has high hydrophilicity, the compatibility with the azo compound represented by the general formula (1) is good, but there is a combination in which crystallization rarely occurs. In that case, since a smooth coating film cannot be obtained, there is a possibility that the orientation regulating force may be affected. Therefore, the (meth) acrylate having the hydrophilic group and the general formula ( A combination with the azo compound represented by 1) is preferred. The presence or absence of crystallization can be determined by, for example, optical observation, spectroscopic analysis, a scattering experiment, or the like.

  The compounding ratio of the azo compound represented by the general formula (1) and the (meth) acrylate having a hydrophilic group is not particularly limited. However, if the amount of the azo compound added is too small, sufficient alignment regulating power is obtained. Since it may not be obtained, and if the amount of the (meth) acrylate having a hydrophilic group is too small, sufficient resistance to the adhesive agent or solvent may not be obtained. The azo compound represented by: is preferably blended so that the (meth) acrylate having a hydrophilic group is 90:10 to 5:95, and is blended so as to be 70:30 to 10:90. More preferably, it is especially preferable to mix | blend so that it may become 60: 40-10: 90. Further, for the same reason as described above, it is preferable to use a blending ratio of the azo compound represented by the general formula (1) and the (meth) acrylate having a hydrophilic group so that the crystallinity does not remarkably increase in the blended state. .

(Optical anisotropic)
The optical anisotropic body of the present invention is an optical in which at least a base material composed of an organic material, a photo-alignment film, and a polymer of a polymerizable liquid crystal composition containing at least one polymerizable liquid crystal compound and a solvent are sequentially laminated. An anisotropic optical body, wherein the solvent can dissolve a part of the substrate.
The present invention will be described more specifically below.

(Application)
As the coating method, a known and commonly used method such as a spin coating method, a gravure printing method, a flexographic printing method, an ink jet method, a die coating method, a cap coating method, or dipping can be performed. Usually, since the solution diluted with the organic solvent is applied, it is dried after application to obtain a coating film for a photo-alignment film.

(Photo-alignment process of photo-alignment film)
The coating film obtained by the above method is irradiated with anisotropy light (hereinafter abbreviated as a photoisomerization step), and the layer of the composition for photo-alignment film is irradiated with light to produce the substrate of the present invention. To do. The light having anisotropy used in the optical anisotropy step includes polarized light such as linearly polarized light and elliptically polarized light, or non-polarized light from a direction oblique to the substrate surface. The polarized light may be either linearly polarized light or elliptically polarized light, but it is preferable to use linearly polarized light having a high extinction ratio in order to perform photoalignment efficiently.
Moreover, since it is necessary to use a polarizing filter or the like in order to obtain polarized light in the light irradiation device, there is a disadvantage that the light intensity irradiated to the film surface is reduced. In the method of irradiating, there is an advantage that a large irradiation intensity can be obtained without requiring a polarizing filter or the like in the irradiation device, and the irradiation time for photo-alignment can be shortened. In this case, the incident angle of non-polarized light is preferably in the range of 10 ° to 80 ° with respect to the normal of the substrate. In consideration of the uniformity of the irradiation energy on the irradiated surface, the pretilt angle obtained, the alignment efficiency, etc., 20 ° A range of ˜60 ° is more preferred, and 45 ° is most preferred.

The light to be irradiated may be light in a wavelength region in which the photo-alignment group of the compound to be used has absorption. For example, when the photo-alignment group has an azobenzene structure, ultraviolet rays having a wavelength of 330 to 500 nm that have strong absorption due to the π → π ^* transition of azobenzene are particularly preferable.
Examples of the light source for irradiation light include xenon lamps, high-pressure mercury lamps, ultra-high pressure mercury lamps, metal halide lamps, ultraviolet lasers such as KrF and ArF, and the like. In the present invention, since the photo-alignment group has an azobenzene structure, an ultra-high pressure mercury lamp having a particularly high emission intensity of ultraviolet light at 365 nm can be used effectively.
By passing the light from the light source through a polarizing prism such as a polarizing filter, Glan-Thompson, or Glan-Teller, it is possible to obtain linearly polarized ultraviolet-visible light.

Moreover, it is particularly preferable that the irradiated light is substantially parallel light regardless of whether polarized light or non-polarized light is used.
Further, when irradiating polarized light, if a photomask is used, liquid crystal alignment ability can be generated in two or more different directions in a pattern on the photo-alignment film. Specifically, after the composition for photo-alignment film of the present invention is applied and dried, the substrate is covered with a photomask, and the entire surface is irradiated with polarized light or non-polarized light to give liquid crystal alignment ability to the exposed portion in a pattern. By repeating this a plurality of times as necessary, liquid crystal alignment ability can be generated in a plurality of directions. Furthermore, when the photomask absorbs a short wavelength of 350 nm or less, since only the UV-visible light exceeding 350 nm irradiated is absorbed by the photo-alignment film, side reactions derived from the short wavelength can be reduced. A preferable liquid crystal alignment ability can be produced.

(Polymerization process of photo-alignment film)
In the case where the alignment film in contact with the substrate of the present invention becomes an alignment film having anisotropy via a photoisomerization reaction and is polymerized in advance, the polymerization is performed after the photo-anisotropy step. Let In this case, it is preferable to add a photopolymerization initiator described later. The polymerization method may be light irradiation or heat, but in the case of light irradiation, the orientation state obtained in the photoisomerization step should not be disturbed. For example, in the case of an azo compound, it is preferably performed at a wavelength other than the absorption band of the azobenzene skeleton. Such light is specifically ultraviolet light having a wavelength of 320 nm or less, but when the photo-alignment film and the polymerizable liquid crystal composition are decomposed by the ultraviolet light having a wavelength of 320 nm or less, the polymerization treatment is performed with the ultraviolet light having a wavelength of 320 nm or more. It may be preferable to perform

  In order to prevent the orientation of the azobenzene skeleton already obtained from being disturbed by ultraviolet light of 320 nm or more, usually, a photopolymerization initiator having a light absorption wavelength band different from the light absorption band of the azobenzene skeleton is used. It is preferred to use. Further, a compound that induces a polymerization reaction by absorbing light having a wavelength longer than the absorption band of a normal photopolymerization initiator and causing energy transfer to the polymerization initiator may be mixed. By these, it can superpose | polymerize, without disturbing the orientation state of the composition for photo-alignment films | membranes fixed by photo-alignment operation. On the other hand, if the light for polymerization is irradiated from the same direction as the photo-alignment operation, or if polarized light irradiation having a polarization plane orthogonal to the absorption transition moment of the azobenzene skeleton is performed, there is no risk of disturbing the obtained alignment state. Any wavelength can be used.

For example, when a photopolymerization initiator is added to the photoalignment material and light is applied to orient the photoalignment material, photoalignment and photopolymerization can be performed simultaneously. In addition, photo-alignment is performed in an atmosphere that inhibits polymerization, for example, in the air, and only photo-alignment is performed. Then, the atmosphere is not inhibited by polymerization, for example, the photo-polymerization is started by changing to nitrogen. It can also be made. In this case, it is preferable to adjust the irradiation amount at the time of photo-alignment so that the photo-polymerization initiator is not consumed while the photo-alignment is performed in an atmosphere of polymerization inhibition.
On the other hand, in the case of polymerization by heat, it is preferably performed at 80 to 250 ° C., and preferably 80 to 160. In this case, it is preferable to add a thermal polymerization initiator.
The photoinitiator used by this invention can use a well-known and usual thing.

  Photopolymerization initiators that can be used with ultraviolet light of 320 nm or less include 1-hydroxycyclohexyl phenyl ketone (“Irgacure 184” manufactured by Ciba Specialty Chemicals), 1- [4- (2-hydroxyethoxy) -phenyl] -2 -Hydroxy-2-methyl-1-propan-1-one, 2-hydroxy-2-methyl-1-phenylpropan-1-one ("Darocur 1173" manufactured by Merck & Co., Inc.) and the like.

  Examples of the photopolymerization initiator having a light absorption wavelength band different from the light absorption band of the azobenzene skeleton include those obtained by combining a near infrared absorbing dye and organic boron described in Japanese Patent No. 3016606. .

  Examples of other photopolymerization initiators include 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one ("Darocur 1116" manufactured by Merck & Co., Inc.), 2-methyl-1-[( Methylthio) phenyl] -2-morpholinopropane-1 (“Irgacure 907” manufactured by Ciba Specialty Chemicals). Benzylmethylketal ("Irgacure 651" manufactured by Ciba Specialty Chemicals). A mixture of 2,4-diethylthioxanthone (“Kayacure DETX” manufactured by Nippon Kayaku Co., Ltd.) and ethyl p-dimethylaminobenzoate (“Kayacure EPA” manufactured by Nippon Kayaku Co., Ltd.), isopropylthioxanthone (“Kantacure” manufactured by Ward Prekinsop) -ITX ") and a mixture of ethyl p-dimethylaminobenzoate, acylphosphine oxide (" Lucirin TPO "manufactured by BASF), and the like. The amount of the photopolymerization initiator used is preferably 10% by mass or less, particularly preferably 0.5 to 5% by mass with respect to the additive.

  In addition, as the thermal polymerization initiator used in the thermal polymerization, known ones can be used, for example, methyl acetoacetate peroxide, cumene hydroperoxide, benzoyl peroxide, bis (4-t-butyl). (Cyclohexyl) peroxydicarbonate, t-butyl peroxybenzoate, methyl ethyl ketone peroxide, 1,1-bis (t-hexyl peroxy) 3,3,5-trimethylcyclohexane, p-pentahydroperoxide, Organic peroxides such as t-butyl hydroperoxide, dicumyl peroxide, isobutyl peroxide, di (3-methyl-3-methoxybutyl) peroxydicarbonate, 1,1-bis (t-butylperoxy) cyclohexane Oxide, 2,2'-azobisisobutyronitrile Azonitrile compounds such as 2,2′-azobis (2,4-dimethylvaleronitrile), azoamidine compounds such as 2,2′-azobis (2-methyl-N-phenylpropion-amidine) dihydrochloride, 2,2 ′ Azoamide compounds such as azobis {2-methyl-N- [1,1-bis (hydroxymethyl) -2-hydroxyethyl] propionamide} and alkylazo such as 2,2′azobis (2,4,4-trimethylpentane) Compounds and the like can be used. 10 mass% or less is preferable with respect to an additive, and, as for the usage-amount of a thermal-polymerization initiator, 0.5-5 mass% is especially preferable.

(Polymerization process of polymerizable liquid crystal composition)
The polymerization operation of the polymerizable liquid crystal composition of the present invention is generally performed by light irradiation such as ultraviolet rays or heating after removing the solvent in the polymerizable liquid crystal composition by heating or the like. When the polymerization is performed by light irradiation, specifically, it is preferable to irradiate ultraviolet light having a wavelength of 390 nm or less, and it is most preferable to irradiate light having a wavelength of 250 to 370 nm. However, when the photo-alignment film and the polymerizable liquid crystal composition cause decomposition or the like due to ultraviolet light having a wavelength of 390 nm or less, it may be preferable to perform a polymerization treatment with ultraviolet light having a wavelength of 390 nm or more.
This light is preferably diffused light and unpolarized light so as not to disturb the orientation of the photoalignable group already obtained.

  On the other hand, the polymerization by heating is preferably performed at a temperature at which the polymerizable liquid crystal composition exhibits a liquid crystal phase or at a temperature lower than that. In particular, when a thermal polymerization initiator that releases radicals by heating is used, the cleavage temperature is the above. It is preferable to use the one in the temperature range. When the thermal polymerization initiator and the photopolymerization initiator are used in combination, the polymerization temperature and the polymerization temperature are set so that the polymerization speeds of both the photo-alignment film and the polymerizable liquid crystal film are not greatly different together with the limitation of the temperature range. It is preferred to select each initiator. Although the heating temperature depends on the transition temperature from the liquid crystal phase to the isotropic phase of the polymerizable liquid crystal composition, the heating temperature is preferably lower than the temperature at which inhomogeneous polymerization is induced by heat. However, if the glass transition point of the base material made of an organic material is exceeded, thermal deformation of the base material becomes remarkable, and therefore, the glass transition point of the room temperature to the base material is preferable. For example, when a polymeric group is a (meth) acryloyl group, it is preferable to carry out at a temperature lower than 90 degreeC.

  In order to stabilize the solvent resistance and heat resistance of the obtained optical anisotropic body, the optical anisotropic body can be heat-treated. In this case, it is preferable to heat above the glass transition point of the prepolymerizable liquid crystal film. Usually, heating within a range not exceeding the glass transition point of a base material made of an organic material is preferable.

  When the optical anisotropic body of the present invention is used, for example, as a raw material for a polarizing film or an alignment film, or for printing ink, paint, protective film, etc., the polymerizable liquid crystal composition used in the present invention has its Depending on the purpose, metals, metal complexes, dyes, pigments, fluorescent materials, phosphorescent materials, surfactants, leveling agents, thixotropic agents, gelling agents, polysaccharides, ultraviolet absorbers, infrared absorbers, antioxidants, ions An exchange resin, a metal oxide such as titanium oxide, or the like may be added.

  The optical anisotropic body of the present invention can be peeled off from the substrate and used alone as an optical anisotropic body, or it can be used as it is without being peeled off from the substrate. In particular, since it is difficult to contaminate other members, it is useful when used as a laminated substrate or by being attached to another substrate. In some cases, optical anisotropic bodies can be laminated over several layers. In that case, the above process may be repeated a plurality of times, and an optically anisotropic laminate can be formed.

Hereinafter, the present invention will be described with reference to synthesis examples, examples, and comparative examples, but the present invention is not limited to these examples. Unless otherwise specified, “part” and “%” are based on mass. The wetting tension was measured according to JIS K6768 “Plastic-film and sheet-wetting tension test method” (the contents of the standard are incorporated by reference in this place).
The UV / ozone treatment was performed using a UV / ozone cleaner manufactured by Filgen Co., Ltd.

(Adjustment of base material 1)
A film made of a cycloolefin derivative as a substrate was irradiated with UV for 5 minutes in air at room temperature using a UV / ozone cleaner. The resulting substrate had a wetting tension of 48 mN / m.
(Adjustment of base material 2)
A film made of a cycloolefin derivative as a substrate was subjected to UV irradiation for 10 minutes in air at room temperature using a UV / ozone cleaner. The resulting substrate had a wetting tension of 60 mN / m.

(Adjustment of base material 3)
A film made of a cycloolefin derivative as a substrate was irradiated with UV for 1 minute in air at room temperature using a UV / ozone cleaner. The resulting substrate had a wetting tension of 35 mN / m.
(Adjustment of base material 4)
A film composed of a triacetyl cellulose derivative as a substrate was irradiated with UV for 2.5 minutes in air at room temperature using a UV / ozone cleaner. The resulting substrate had a wetting tension of 48 mN / m.
(Adjustment of base material 5)
A film made of a triacetylcellulose derivative as a substrate was irradiated with UV for 10 minutes in air at room temperature using a UV / ozone cleaner. The resulting substrate had a wetting tension of 58 mN / m.
(Preparation of composition AL-1 for photo-alignment film)

式（Ａ）で表される化合物０．５部を２−（２−エトキシエトキシ）エタノール４９部に溶解させた後、２−ブトキシエタノール４９部を加えて光配向膜用組成物Ａを得た。得られた溶液を０．４５μｍのメンブランフィルターでろ過し、光配向膜用組成物ＡＬ−１を得た。

After 0.5 part of the compound represented by the formula (A) was dissolved in 49 parts of 2- (2-ethoxyethoxy) ethanol, 49 parts of 2-butoxyethanol was added to obtain a composition A for a photoalignment film. . The obtained solution was filtered with a 0.45 μm membrane filter to obtain a photoalignment film composition AL-1.

(Adjustment of composition AL-2 for photo-alignment film)
0.5 part of the compound represented by the formula (A) was dissolved in 49 parts of 2- (2-ethoxyethoxy) ethanol to obtain a solution 1. Next, 1 part of DA-212 (manufactured by Nagase ChemteX Corporation) was dissolved in 49 parts of 2-butoxyethanol to obtain Solution 2. The solution 2 was added to the solution 1, and the composition B for photo-alignment films was obtained. The obtained solution was filtered with a 0.45 μm membrane filter to obtain a photoalignment film composition AL-2.

(Composition AL-3 for photo-alignment film)
A solution 1 was obtained by dissolving 0.5 part of the compound represented by the formula (A) in 33 parts of water. Next, 1 part of DA-212 (manufactured by Nagase ChemteX Corporation) was dissolved in 33 parts of 2-butoxyethanol to obtain Solution 2. Solution 1 and solution 2 were added with dipropylene glycol monomethyl ether n to obtain composition C for photo-alignment film. The obtained solution was filtered with a 0.45 μm membrane filter to obtain a photoalignment film composition AL-3.

(Preparation of polymerizable liquid crystal composition LC-1)
After dissolving 15 parts of the compound represented by the formula (B) and 15 parts of the compound represented by the formula (C) in 70 parts of propylene glycol monomethyl ether, 1.2 parts of Irgacure 907 (manufactured by Ciba Specialty Chemicals Co., Ltd.) Then, 0.3 part of an acrylic copolymer represented by the formula (D) was added to obtain a solution. The obtained solution was filtered with a 0.45 μm membrane filter to obtain a polymerizable liquid crystal composition (LC-1).

Example 1
The composition for optical alignment film AL-1 was applied onto the substrate 1 with a spin coater and dried at 80 ° C. for 1 minute. The dry film thickness at this time was 15 nm.
Next, the ultra-high pressure mercury lamp is applied with a linearly polarized light of visible ultraviolet light (irradiation intensity: 20 mW / cm ² ) in the vicinity of a wavelength of 365 nm through a wavelength cut filter, a bandpass filter, and a polarizing filter. The film was irradiated from the vertical direction to obtain a photo-alignment film. The irradiation amount was 100 mJ / cm ² .
Polymeric liquid crystal composition LC-1 is applied onto the obtained photo-alignment film with a spin coater, dried at 80 ° C. for 2 minutes, and then irradiated with 1 J / cm ² of ultraviolet light in a nitrogen atmosphere to obtain uniform optical anisotropy. Got the body. The retardation was 270 nm. The result of observing the film state of the obtained optical anisotropic body was evaluated according to the appearance evaluation. The results are shown in Table 1.

(Appearance evaluation)
A: There are no defects visually, and there are no defects even when observed with a polarizing microscope. B: There are no defects visually, but there are non-oriented portions in the observation with a polarizing microscope. C: There are no defects visually, but a polarizing microscope. Non-orientation part exists as a whole by observation D: Some defects are visually observed, and non-orientation part exists as a whole even by polarization microscope observation E: Unevenness in the entire photo-alignment film by observation Has occurred

(Adhesion evaluation)
Moreover, in order to evaluate the adhesive force of the obtained optical anisotropic body, the obtained optical anisotropic body was cut into a grid pattern with a cutter on a 1 cm square of the optical anisotropic body to form a 2 mm square grid. Next, cellophane tape was applied to the grid area and pulled up in the vertical direction to count the number of remaining grid lines. The above operation was repeated 5 times to obtain an average value. The obtained results are shown in Table 1.
Hereinafter, in the same manner as in Example 1, Examples 2 to 9 and Comparative Examples 1 to 3 were performed. The results obtained are shown together in Table 1.

From the results shown in Table 1, the optical anisotropic bodies obtained in Examples 1 to 9 are free from defects in appearance, are in a transparent film state, and are excellent in adhesiveness. On the other hand, although the optical anisotropic bodies of Comparative Examples 1 to 3 had no appearance defect, the adhesiveness was lowered.

  Therefore, it can be seen that the polymerizable liquid crystal composition of the present invention provides an optically anisotropic body having no appearance defect and excellent adhesion to the substrate.

Claims (20)

An optical anisotropic body in which at least a base material made of an organic material, a photo-alignment film, and a polymer film of a polymerizable liquid crystal composition containing at least one polymerizable liquid crystal compound are sequentially laminated is defined by JIS K6768. An optical anisotropic body, wherein the wetting tension of the substrate to be formed is greater than the surface tension of the composition for photo-alignment film used for the photo-alignment film. 2. The optical anisotropic body according to claim 1, wherein the wetting tension of the substrate is 40 to 65 mN / m. The optical anisotropic body according to claim 1 or 2, wherein the polymerizable liquid crystal composition contains two or more kinds of rod-like polymerizable liquid crystal compounds having at least two polymerizable functional groups. The said polymerizable liquid crystal composition contains the rod-like polymerizable liquid crystal compound having at least two polymerizable functional groups and the rod-like polymerizable liquid crystal compound having one polymerizable functional group. Optical anisotropic. The optical anisotropic body according to claim 3 or 4, wherein the rod-like polymerizable liquid crystal compound is represented by the general formula (1).

(Wherein P represents a reactive functional group, Sp represents a spacer group having 1 to 20 carbon atoms, m represents 0 or 1, MG represents a mesogenic group or a mesogenic support group, and R ¹ represents Represents a halogen atom, a cyano group or an alkyl group having 1 to 25 carbon atoms, and the alkyl group may be substituted by one or more halogen atoms or CN, and one CH ₂ present in the group. Group or two or more non-adjacent CH ₂ groups are each independently of each other such that —O—, —S—, —NH—, —N (CH ₃ ) -, -CO-, -COO-, -OCO-, -OCOO-, -SCO-, -COS- or -C≡C- may be substituted, or R ¹ may be represented by the general formula (1-a)

(Wherein P represents a reactive functional group, Sp represents a spacer group having 1 to 20 carbon atoms, and m represents 0 or 1). ) In the general formula (1), Sp represents an alkylene group (the alkylene group may be substituted with one or more halogen atoms or CN, and one CH ₂ group present in the group or adjacent thereto). Two or more CH ₂ groups, which are independent of each other, are in a form in which oxygen atoms are not directly bonded to each other, —O—, —S—, —NH—, —N (CH ₃ ) —, —CO— , -COO-, -OCO-, -OCOO-, -SCO-, -COS- or -C≡C- may be substituted.) MG is represented by the general formula (1-b)

(In the formula, A1, A2 and A3 are each independently 1,4-phenylene group, 1,4-cyclohexylene group, 1,4-cyclohexenyl group, tetrahydropyran-2,5-diyl group, 1, 3-dioxane-2,5-diyl group, tetrahydrothiopyran-2,5-diyl group, 1,4-bicyclo (2,2,2) octylene group, decahydronaphthalene-2,6-diyl group, pyridine- 2,5-diyl group, pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 2,6-naphthylene group, Phenanthrene-2,7-diyl group, 9,10-dihydrophenanthrene-2,7-diyl group, 1,2,3,4,4a, 9,10a-octahydrophenanthrene 2,7-diyl group or fluorene 2, Represents a 7-diyl group, the 1,4-phenylene group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 2,6-naphthylene group, phenanthrene-2,7-diyl group, 9 , 10-Dihydrophenanthrene-2,7-diyl group 1,2,3,4,4a, 9,10a- octahydrophenanthrene 2,7-diyl group and fluorene 2,7-diyl group is 1 or more F as _{substituents, Cl, CF 3, OCF 3} , cyano Group, an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkanoyl group, an alkanoyloxy group, an alkenyl group having 2 to 8 carbon atoms, an alkenyloxy group, an alkenoyl group or an alkenoyloxy group. , Z0, Z1, Z2 and Z3 are each independently -COO-, -OCO-, -CH ₂ CH _2- , -OCH _2- , -CH ₂ O-, -CH = CH-, -C≡C -, -CH = CHCOO-, -OCOCH = CH-, -CH ₂ CH ₂ COO-, -CH ₂ CH ₂ OCO-, -COO CH ₂ CH _2- , -OCOCH ₂ CH _2- , -CONH-,- NHCO- or a single bond, n represents 0, 1 or 2), and P represents a general formula (1-c), general formula (1-d) and general formula (1- e)

(In the formula, R ²¹ , R ²² , R ²³ , R ³¹ , R ³² , R ³³ , R ⁴¹ , R ⁴² and R ⁴³ are each independently a hydrogen atom, a halogen atom or an alkyl group having 1 to 5 carbon atoms. And n represents 0 or 1. The optically anisotropic body according to claim 5, which represents a substituent selected from the group consisting of substituents represented by: General formula (2)

Wherein m represents 0 or 1, W ¹ and W ² each independently represent a single bond, —O—, —COO— or —OCO—, and Y ¹ and Y ² each independently represent — COO- or -OCO- is represented, and r and s each independently represent an integer of 2 to 18, the 1,4-phenylene group present in the formula is an alkyl group or alkoxy group having 1 to 7 carbon atoms , An alkanoyl group, a cyano group, or a halogen atom, which may be substituted by one or more). General formula (3)

(In the formula, Z ¹ represents a hydrogen atom, a halogen atom, a cyano group or a hydrocarbon group having 1 to 20 carbon atoms, Z ² represents a hydrogen atom or a methyl group, t represents 0 or 1, A, B and C are each independently a 1,4-phenylene group, a 1,4-phenylene group in which a non-adjacent CH group is substituted with nitrogen, a 1,4-cyclohexylene group, one or two non-adjacent CH ₂ Represents a 1,4-cyclohexylene group or 1,4-cyclohexenylene group in which the group is substituted with an oxygen or sulfur atom, and the 1,4-phenylene group present in the formula is an alkyl having 1 to 7 carbon atoms Group, an alkoxy group, an alkanoyl group, a cyano group or a halogen atom, and Y ³ and Y ⁴ are each independently a single bond, —CH ₂ CH ₂ —, —CH ₂ O—, _{-OCH 2 -, - COO -,} - OCO -, - C≡C -, - CH = CH -, - CF = CF -, - (CH 2) 4 -, - CH 2 CH 2 CH 2 O -, - OCH ₂ CH ₂ CH _2- , -CH = CHCH ₂ CH _2- , -CH _{2 CH 2 CH = CH -, -} CH = CHCOO -, - OCOCH = CH -, - CH 2 CH 2 COO -, - CH 2 CH 2 OCO -, - COO CH 2 CH 2 - or -OCOCH ₂ CH ₂ - and And Y ⁵ represents a single bond, —O—, —COO—, —OCO—, or —CH═CHCOO—). General formula (4)

(Wherein Z ³ represents a hydrogen atom, a halogen atom, a cyano group or a hydrocarbon group having 1 to 20 carbon atoms, Z ⁴ represents a hydrogen atom or a methyl group, W ³ represents a single bond, —O—, -COO- or -OCO-, v represents an integer of 2 to 18, u represents 0 or 1, D, E and F are each independently a 1,4-phenylene group or a non-adjacent CH group. 1,4-phenylene group substituted with nitrogen, 1,4-cyclohexylene group, 1,4-cyclohexylene group in which one or two non-adjacent CH ₂ groups are substituted with oxygen or sulfur atoms, 1, Represents a 4-cyclohexenylene group, but the 1,4-phenylene group present in the formula is substituted by one or more alkyl groups, alkoxy groups, alkanoyl groups, cyano groups or halogen atoms having 1 to 7 carbon atoms. Y ⁶ and Y ⁷ are each independently a single bond, —CH ₂ CH ₂ —, —CH ₂ O—, —OCH ₂ —, —COO—, —OCO—, —C≡C—, — CH = CH-, -CF = CF _{-, - (CH 2) 4} -, - CH 2 CH 2 CH 2 O -, - OCH 2 CH 2 CH 2 -, - CH = CHCH 2 CH 2 -, - CH 2 CH 2 CH = CH -, - CH = CHCOO -, - OCOCH = CH -, - CH 2 CH 2 COO -, - CH 2 CH 2 OCO -, - COO CH 2 CH 2 - or -OCOCH ₂ CH ₂ - represents, Y ⁸ represents a single bond, - The optical anisotropic body according to claim 5, comprising a compound represented by the formula: O—, —COO—, —OCO— or —CH═CHCOO—. The optically anisotropic body according to claim 1, wherein the polymerizable liquid crystal compound in the polymerizable liquid crystal composition contains two or more kinds of discotic liquid crystal compounds having at least one polymerizable functional group. A discotic liquid crystal compound having at least one polymerizable functional group is composed of a benzene derivative, a triphenylene derivative, a truxene derivative, a phthalocyanine derivative or a cyclohexane derivative as a mother nucleus at the center of the molecule, and a linear alkyl group or a linear alkoxy group. The optically anisotropic body according to claim 1 or 9, wherein the optically anisotropic body has a structure in which a substituted benzoyloxy group is radially substituted as a side chain thereof.
The optically anisotropic body according to claim 9 or 10, wherein the discotic liquid crystal compound having at least one polymerizable functional group is represented by the general formula (5).

(In the formula, each R ⁵ independently represents a substituent represented by the general formula (5-a).)

(In the formula, R ⁶ and R ⁷ each independently represent a hydrogen atom, a halogen atom or a methyl group, and R ⁸ represents an alkoxy group having 1 to 20 carbon atoms, and the hydrogen atom in the alkoxy group represents a general formula. (It may be substituted with a substituent represented by (5-b), general formula (5-c) or general formula (5-d))

Wherein R ⁸¹ , R ⁸² , R ⁸³ , R ⁸⁴ , R ⁸⁵ , R ⁸⁶ , R ⁸⁷ , R ⁸⁸ and R ⁸⁹ are each independently a hydrogen atom, a halogen atom or an alkyl group having 1 to 5 carbon atoms. And n represents 0 or 1.) An optically anisotropic body, wherein the polymerizable liquid crystal compound in the polymerizable liquid crystal composition contains two or more banana-type liquid crystal compounds having at least one polymerizable functional group. The optical anisotropic body according to claim 1, wherein the solvent in the polymerizable liquid crystal composition contains a solvent that dissolves the base material and a solvent that does not dissolve the base material. An optical anisotropic body in which a polymerized liquid crystal layer obtained by polymerizing after coating and drying a polymerizable liquid crystal composition containing at least a substrate made of an organic material, a photo-alignment film, and a solvent for dissolving the substrate is sequentially laminated. The optical anisotropic body according to claim 1 or 13, wherein the substrate is made of polyester, polystyrene, polyolefin, cellulose derivative, polyarylate, or polycarbonate. 15. The optical anisotropic body according to claim 1, wherein the photo-alignment film is a compound having at least one cinnamoyl group, a chalcone group, a coumarin group, an azo group, or an arylethene derivative. . 16. The optical anisotropic body according to claim 1, wherein the optical alignment film contains at least an azo compound represented by the general formula (6).

(In the general formula (6), R ¹ and R ² are each independently a hydroxy group, or a (meth) acryloyl group, a (meth) acryloyloxy group, a (meth) acryloylamino group, a vinyl group, a vinyloxy group and a maleimide group. Represents a polymerizable functional group selected from the group consisting of:
A ¹ and A ² each independently represent a single bond or a divalent hydrocarbon group which may be substituted by an alkoxy group, and B ¹ and B ² each independently represent a single bond, —O—, —CO -O-, -O-CO-, -CO-NH-, -NH-CO-, -NH-CO-O- or -O-CO-NH-, but in the bond of R ¹ and R ² , Does not form a —O—O— bond,
m and n each independently represents an integer of 0 to 4, but when m or n is 2 or more, a plurality of A ¹ , B ¹ , A ² and B ² may be the same or different. A ¹ or A ² sandwiched between two B ¹ or B ² represents a divalent hydrocarbon group which may be substituted with an alkoxy group,
R ^{3 to} R ⁶ are each independently a hydrogen atom, a halogen atom, a halogenated alkyl group, an allyloxy group, a cyano group, a nitro group, an alkyl group, a hydroxyalkyl group, an alkoxy group, a carboxy group or an alkali metal salt thereof, an alkoxy Carbonyl group, halogenated methoxy group, hydroxy group, sulfo group or alkali metal salt thereof, amino group, carbamoyl group, sulfamoyl group or (meth) acryloyl group, (meth) acryloyloxy group, (meth) acryloylamino group, vinyl group Represents a polymerizable functional group selected from the group consisting of a vinyloxy group and a maleimide group. ) The photo-alignment film light contains at least a compound having a hydrophilic group and a (meth) acryloyloxy group, and a polymer compatible with the azo compound represented by the general formula (7). The optical anisotropic body of 13-16.

(In the general formula (7), R ¹ and R ² are each independently a hydroxy group, a (meth) acryloyl group, a (meth) acryloyloxy group, a (meth) acryloylamino group, a vinyl group, a vinyloxy group, or a glycidyl group. And represents a polymerizable functional group selected from the group consisting of maleimide groups,
A ¹ and A ² each independently represent a single bond or a divalent hydrocarbon group which may be substituted by an alkoxy group, and B ¹ and B ² each independently represent a single bond, —O—, —CO -O-, -O-CO-, -CO-NH-, -NH-CO-, -NH-CO-O- or -O-CO-NH-, but in the bond of R ¹ and R ² , Does not form a —O—O— bond,
m and n each independently represents an integer of 0 to 4, but when m or n is 2 or more, a plurality of A ¹ , B ¹ , A ² and B ² may be the same or different. A ¹ or A ² sandwiched between two B ¹ or B ² represents a divalent hydrocarbon group which may be substituted with an alkoxy group,
R ^{3 to} R ⁶ are each independently a hydrogen atom, a halogen atom, a halogenated alkyl group, an allyloxy group, a cyano group, a nitro group, an alkyl group, a hydroxyalkyl group, an alkoxy group, a carboxy group or an alkali metal salt thereof, an alkoxy Carbonyl group, halogenated methoxy group, hydroxy group, sulfo group or alkali metal salt thereof, amino group, carbamoyl group, sulfamoyl group or (meth) acryloyl group, (meth) acryloyloxy group, (meth) acryloylamino group, vinyl group Represents a polymerizable functional group selected from the group consisting of a vinyloxy group and a maleimide group. ) The optical anisotropic body according to claim 1, 13 to 17, wherein the photo-alignment film is a layer in which liquid crystal alignment ability is generated in two or more different directions in a pattern. At least a base material made of an organic material, a photo-alignment film, a polymerized liquid crystal layer obtained by polymerizing after coating and drying a polymerizable liquid crystal composition containing a solvent that dissolves the base material, are sequentially laminated, and further a photo-alignment film, The optical anisotropic body according to claim 1, 13 to 18, wherein a polymerized liquid crystal layer obtained by polymerizing a polymerizable liquid crystal composition containing a solvent for dissolving the base material after coating and drying is sequentially formed.