KR20200116553A - Cured-film-forming composition, alignment material, and phase-difference material - Google Patents

Abstract

[Problem] To provide a cured film forming composition suitable for formation of a cured film having excellent liquid crystal orientation and adhesion durability, provide an alignment material, and provide a retardation material using the alignment material.
[Solution] The cured film-forming composition includes (A) a photo-alignment group, a compound having one selected from the group consisting of a hydroxy group, a carboxyl group, an amino group, and an alkoxysilyl group, (B) at least one of a hydroxy group and a carboxyl group It contains a polymer having and (C) a compound having a hydroxyl group and a (meth)acrylic group other than the component (A). Using this cured film forming composition, a cured film is formed, and an alignment material is formed using a photo-alignment technique. A polymerizable liquid crystal is applied on the alignment material and cured to obtain a retardation material.

Description

Cured film forming composition, orientation material, and retardation material {CURED-FILM-FORMING COMPOSITION, ALIGNMENT MATERIAL, AND PHASE-DIFFERENCE MATERIAL}

The present invention relates to a cured film forming composition, an alignment material, and a retardation material.

In recent years, in the field of displays such as a television using a liquid crystal panel, development of a 3D display capable of enjoying a 3D image is in progress as an attempt to increase performance. In the 3D display, for example, an image with a three-dimensional effect can be displayed by visually recognizing an image for the right eye to the viewer's right eye and visually recognizing the image for the left eye to the left eye of the observer.

There are various types of 3D display methods for displaying 3D images. As methods that do not require dedicated glasses, a lenticular lens method and a parallax barrier method are known.

In addition, as one of the display methods in which an observer wears glasses to observe a 3D image, a circular polarization glasses method or the like is known (see, for example, Patent Document 1).

In the case of a 3D display of the circular polarization glasses system, a retardation material is usually disposed on a display element that forms an image such as a liquid crystal panel. In this phase difference material, a plurality of two types of phase difference regions having different phase difference characteristics are regularly arranged, respectively, to constitute a patterned phase difference material. On the other hand, hereinafter, in the present specification, a phase difference material patterned so as to arrange a plurality of phase difference regions having different phase difference characteristics is referred to as a patterned phase difference material.

The patterned retardation material can be produced, for example, by optically patterning a retardation material made of a polymerizable liquid crystal, as disclosed in Patent Document 2. Optical patterning of a retardation material made of a polymerizable liquid crystal uses a known photo-alignment technique for forming an alignment material of a liquid crystal panel. That is, a coating film made of a photo-alignment material is provided on a substrate, and two types of polarized light having different polarization directions are irradiated thereto. Then, a photo-alignment film is obtained as an alignment material in which two kinds of liquid crystal alignment regions having different alignment control directions of the liquid crystal are formed. A solution phase difference material containing a polymerizable liquid crystal is applied on the photo-alignment film to achieve alignment of the polymerizable liquid crystal. After that, the aligned polymerizable liquid crystal is cured to form a patterned retardation material.

In forming an alignment material using a photo-alignment technique of a liquid crystal panel, as an available photo-alignment material, an acrylic resin or polyimide resin having a photo-dimerization site such as a cinnamoyl group and a chalcone group in the side chain is known. It is reported that these resins exhibit the ability to control the alignment of liquid crystals (hereinafter, also referred to as liquid crystal alignment properties) by irradiating with polarized UV light (refer to Patent Documents 3 to 5).

Japanese Patent Laid-Open No. H10-232365 Japanese Patent Laid-Open No. 2005-49865 Japanese Patent No. 3611342 Specification Japanese Patent Publication No. 2009-058584 Japanese Patent Publication No. 2001-517719

As described above, the patterned retardation material is constituted by laminating a layer of cured polymerizable liquid crystal on the photo-alignment film as an alignment material. In addition, the patterned retardation material having such a stacked structure can be used in the configuration of a 3D display as it is stacked.

The 3D display is sometimes used as a home television, and high reliability, particularly, long-term durability is required. Accordingly, durability is also required for the constituent members of the 3D display. Therefore, also in the patterned phase difference material, long-term durability becomes an essential performance in addition to having optical patterning with high accuracy or having high light transmission characteristics.

However, the conventional patterned retardation material has a problem in adhesion between the photo-alignment film and the layer of the polymerizable liquid crystal. For example, between the photo-alignment film and the layer of the polymerizable liquid crystal, peeling is likely to occur from the initial stage of formation, and there is an adhesive property at the initial stage of formation, but the adhesiveness decreases with the passage of time and peeling is likely to occur.

Among them, peeling between the photo-alignment film and the layer of the polymerizable liquid crystal, which occurs with the passage of time, becomes a defect in a 3D display that is actually used and causes a deterioration in the display quality of the 3D display. Accordingly, high-precision optical patterning is possible, light transmission characteristics are excellent, and further, a patterned retardation material having excellent durability is required. In particular, there is a need for a patterned retardation material having excellent adhesion between the photo-alignment film and the layer of the polymerizable liquid crystal at the initial stage of formation, and durability (hereinafter referred to as adhesion durability in the present specification) to maintain the excellent adhesion for a long time. .

The present invention has been made based on the above findings and examination results. That is, an object of the present invention is to provide a cured film forming composition suitable for formation of a cured film having excellent liquid crystal orientation and light transmission characteristics and excellent adhesion durability. In particular, it is used as an alignment material, and when a layer of a polymerizable liquid crystal is disposed thereon, it exhibits excellent liquid crystal orientation and light transmittance, and has excellent adhesion durability that can maintain adhesion between the layers of the polymerizable liquid crystal for a long time. It is to provide a cured film-forming composition that forms a film.

It is an object of the present invention to provide an alignment material having excellent liquid crystal orientation and light transmission properties and excellent adhesion durability.

It is an object of the present invention to provide a retardation material capable of highly accurate optical patterning and excellent durability.

Other objects and advantages of the present invention will become apparent from the following description.

The first aspect of the present invention,

(A) a compound having a photo-alignment group and one selected from the group consisting of a hydroxy group, a carboxyl group, an amino group and an alkoxysilyl group,

(B) a polymer having at least one of a hydroxy group and a carboxyl group, and

(C) Compounds having a hydroxyl group and a (meth)acrylic group other than the component (A)

It relates to a cured film-forming composition comprising:

In the first aspect of the present invention, it is preferable that the compound of the component (A) is a compound having a photo-alignment group and a hydroxy group.

In the first aspect of the present invention, it is preferable that the compound of the component (C) has one or more hydroxyl groups and one (meth)acrylic group.

In the first aspect of the present invention, it is preferable to contain (D) a crosslinking agent.

In the first aspect of the present invention, it is preferable to contain (E) a crosslinking catalyst.

The second aspect of the present invention relates to an orientation material obtained by using the cured film forming composition of the first aspect of the present invention.

A third aspect of the present invention relates to a retardation material having a cured film obtained from the cured film forming composition of the first aspect of the present invention.

According to the first aspect of the present invention, it is possible to provide a cured film forming composition suitable for formation of a cured film having excellent liquid crystal orientation and light transmittance and excellent in adhesion durability.

According to the second aspect of the present invention, an alignment material having excellent liquid crystal orientation and light transmittance and excellent adhesion durability can be provided.

According to the third aspect of the present invention, high-precision optical patterning is possible and a retardation material excellent in durability can be provided.

As described above, in order to manufacture a patterned retardation material having excellent durability, an alignment material having excellent adhesion durability, in particular, an alignment material having excellent adhesion durability between layers of cured polymerizable liquid crystals is required. And there is a demand for a cured film forming composition suitable for formation of an alignment material having such performance.

In order to meet the above-described requirements, the inventors of the present invention conducted a thorough study. As a result, a cured film obtained from a cured film-forming composition having a specific composition has excellent light transmittance, and a liquid crystal orientation that regulates liquid crystal orientation by polarization exposure. And found that it could be used as an orientation material. In addition, the present inventors have found that the cured film obtained from the cured film forming composition having the specific composition exhibits excellent adhesion durability between the layers of the polymerizable liquid crystal polymerized thereon. That is, the cured film obtained from the cured film forming composition having a specific composition of the present invention can constitute a photo-alignment film excellent in adhesion durability between layers of a polymerizable liquid crystal.

Hereinafter, the cured film-forming composition of the present invention will be described in detail with reference to specific examples such as components. Then, the cured film and alignment material of the present invention using the cured film forming composition of the present invention, and the retardation material and liquid crystal display device formed by using the alignment material will be described.

<Cured film forming composition>

The cured film-forming composition of this embodiment of the present invention includes (A) a photo-alignment group, a low molecular weight alignment component, which is a compound having one selected from the group consisting of a hydroxy group, a carboxyl group, an amino group and an alkoxysilyl group, (B) It is a thermosetting cured film-forming composition having photo-alignment containing a polymer having at least one of a hydroxyl group and a carboxyl group, and a compound having a hydroxyl group and a (meth)acrylic group other than the (C) component (A). Furthermore, the cured film formation composition of this embodiment can contain a crosslinking agent as (D) component in addition to (A) component, (B) component, and (C) component. And, in addition to the component (A), the component (B), the component (C) and the component (D), a crosslinking catalyst can be contained as a component (E). Further, other additives may be contained as long as the effect of the present invention is not impaired. Furthermore, it may contain a solvent.

Hereinafter, the details of each component will be described.

[(A) component]

(A) component of the cured film formation composition of this embodiment is a low molecular weight orientation component. (A) component is a component that imparts photo-alignment to the cured film of this embodiment obtained from the cured film-forming composition of the present embodiment, and becomes a low-molecular photo-alignment component compared to the polymer of component (B) to be described later as a base. .

In the cured film forming composition of the present embodiment, the low-molecular alignment component as the component (A) is a compound having a photo-alignment group and one group selected from the group consisting of a hydroxy group, a carboxyl group, an amino group, and an alkoxysilyl group. I can.

On the other hand, in the present invention, the photo-alignment group refers to a functional group of a structural portion to be photo-dimerized or photo-isomerized.

The photo-dimerization structural part that the compound of component (A) may have as a photo-alignment group is a part that forms a dimer by light irradiation, and specific examples thereof include cinnamoyl group, chalcone group, coumarin group, And anthracene group. Among these, a cinnamoyl group is preferred because of its high transparency in the visible region and high photo-dimerization reactivity.

In addition, the structural moiety for photoisomerization that the compound of component (A) may have as a photo-alignment group refers to a structural moiety that changes into a cis body and a trans form by light irradiation, and specific examples thereof include azobenzene structure, stilbene structure, etc. And a portion consisting of. Among these, an azobenzene structure is preferred from the viewpoint of high reactivity.

The compound which has the photo-alignment group of (A) component and any one of a substituent selected from a hydroxy group, a carboxyl group, an amino group, and an alkoxysilyl group is a compound represented by the following formula, for example.

[Formula 1]

In the above formula, A ¹ and A ² each independently represent a hydrogen atom or a methyl group, and X ¹¹ is one selected from a single bond, an ether bond, an ester bond, an amide bond, a urethane bond, an amino bond, or a combination thereof. Or it shows a structure formed by bonding of 1 to 3 substituents selected from an alkylene group having 1 to 18 carbon atoms, a phenylene group, a biphenylene group, or a combination thereof through two or more bonds. X ¹² represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 18 carbon atoms, a phenyl group, a biphenyl group, or a cyclohexyl group. The alkyl group, phenyl group, biphenyl group and cyclohexyl group having 1 to 18 carbon atoms may be bonded to neighboring groups through covalent bonds, ether bonds, ester bonds, amide bonds, or urea bonds.

X ¹³ represents a hydroxy group, a mercapto group, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a phenoxy group, a biphenyloxy group, or a phenyl group. Each of X ¹⁴ independently represents a single bond, an alkylene group having 1 to 20 carbon atoms, an aromatic cyclic group, or an aliphatic cyclic group. Here, the alkylene group having 1 to 20 carbon atoms may be branched or linear. X ¹⁵ represents a hydroxy group, a carboxyl group, an amino group or an alkoxysilyl group. X represents a single bond, an oxygen atom or a sulfur atom. Meanwhile, when a benzene ring is included in the substituent, the benzene ring is the same or different 1 selected from an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, a trifluoromethyl group, and a cyano group. Or it may be substituted by a plurality of substituents.

In the above formula, R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ and R ¹⁸ are each independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy having 1 to 4 carbon atoms Group, a halogen atom, a trifluoromethyl group, or a cyano group.

(A) As a specific example of the compound which has a photo-alignment group and a hydroxy group which is a component, for example, 4-(8-hydroxyoctyloxy)cinnamic acid methyl ester, 4-(6-hydroxyhexyloxy)cinnamic acid Methyl ester, 3-methoxy-4-(6-hydroxyhexyloxy) cinnamic acid methyl ester, 4-(4-hydroxybutyloxy) cinnamic acid methyl ester, 4-(3-hydroxypropyloxy) cinnamic acid methyl ester , 4-(2-hydroxyethyloxy) cinnamic acid methyl ester, 4-hydroxymethyloxy cinnamic acid methyl ester, 4-hydroxy cinnamic acid methyl ester, 4-(8-hydroxyoctyloxy) cinnamic acid ethyl ester, 4-( 6-hydroxyhexyloxy) cinnamic acid ethyl ester, 4-(4-hydroxybutyloxy) cinnamic acid ethyl ester, 4-(3-hydroxypropyloxy) cinnamic acid ethyl ester, 4-(2-hydroxyethyloxy) Cinnamic acid ethyl ester, 4-hydroxymethyloxy cinnamic acid ethyl ester, 4-hydroxy cinnamic acid ethyl ester, 4-(8-hydroxyoctyloxy) cinnamic acid phenyl ester, 4-(6-hydroxyhexyloxy) cinnamic acid phenyl ester , 4-(4-hydroxybutyloxy) cinnamic acid phenyl ester, 4-(3-hydroxypropyloxy) cinnamic acid phenyl ester, 4-(2-hydroxyethyloxy) cinnamic acid phenyl ester, 4-hydroxymethyloxy cinnamic acid Phenyl ester, 4-hydroxycinnamic acid phenyl ester, 4-(8-hydroxyoctyloxy) cinnamic acid biphenyl ester, 4-(6-hydroxyhexyloxy) cinnamic acid biphenyl ester, 4-(4-hydroxybutyl Oxy) cinnamic acid biphenyl ester, 4-(3-hydroxypropyloxy) cinnamic acid biphenyl ester, 4-(2-hydroxyethyloxy) cinnamic acid biphenyl ester, 4-hydroxymethyloxy cinnamic acid biphenyl ester, 4- Cinnamic acid biphenyl ester, cinnamic acid 8-hydroxyoctyl ester, cinnamic acid 6-hydroxyhexyl ester, cinnamic acid 4-hydroxybutyl ester, cinnamic acid 3-hydroxypropyl ester, cinnamic acid 2-hydroxyethyl ester, cinnamic acid hydroxy Methyl ester, 4-(8-hydroxyoctyloxy)chalcone, 4-(6-hydroxyhexyloxy)chalcone, 4-(4-hydroxybutyloxy)chalcone, 4-(3-hydroxypropyloxy) Chalcone, 4-(2-hydroxyethyloxy)chalcone, 4-hydroxymethyloxychalcone, 4-hydroxychalcone, 4'- (8-hydroxyoctyloxy)chalcone, 4'-(6-hydroxyhexyloxy)chalcone, 4'-(4-hydroxybutyloxy)chalcone, 4'-(3-hydroxypropyloxy)chalcone, 4'-(2-hydroxyethyloxy)chalcone, 4'-hydroxymethyloxychalcone, 4'-hydroxychalcone, 7-(8-hydroxyoctyloxy)coumarin, 7-(6-hydroxyhexyloxy) Si) Coumarin, 7-(4-hydroxybutyloxy)coumarin, 7-(3-hydroxypropyloxy)coumarin, 7-(2-hydroxyethyloxy)coumarin, 7-hydroxymethyloxycoumarin, 7- Hydroxycoumarin, 6-hydroxyoctyloxycoumarin, 6-hydroxyhexyloxycoumarin, 6-(4-hydroxybutyloxy)coumarin, 6-(3-hydroxypropyloxy)coumarin, 6-(2-hydro Roxyethyloxy)coumarin, 6-hydroxymethyloxycoumarin, 6-hydroxycoumarin, 4-[4-(8-hydroxyoctyloxy)benzoyl] cinnamic acid methyl ester, 4-[4-(6-hydroxyhex) Siloxy)benzoyl]cinnamic acid methyl ester, 4-[4-(4-hydroxybutyloxy)benzoyl]cinnamic acid methyl ester, 4-[4-(3-hydroxypropyloxy)benzoyl]cinnamic acid methyl ester, 4-[ 4- (2-hydroxyethyloxy) benzoyl] cinnamic acid methyl ester, 4-[4-hydroxymethyloxybenzoyl] cinnamic acid methyl ester, 4-[4-hydroxybenzoyl] cinnamic acid methyl ester, 4-[4-( 8-hydroxyoctyloxy)benzoyl]ethyl cinnamate, 4-[4-(6-hydroxyhexyloxy)benzoyl] ethyl cinnamon, 4-[4-(4-hydroxybutyloxy)benzoyl] ethyl cinnamate Ester, 4-[4-(3-hydroxypropyloxy)benzoyl] ethyl cinnamic ester, 4-[4-(2-hydroxyethyloxy) benzoyl] ethyl cinnamic ester, 4-[4-hydroxymethyloxybenzoyl ] Cinnamic acid ethyl ester, 4-[4-hydroxybenzoyl] cinnamic acid ethyl ester, 4-[4-(8-hydroxyoctyloxy)benzoyl] cinnamic acid tertiary butyl ester, 4-[4-(6-hydroxyhex) Siloxy)benzoyl]Cinnamic acid tertiary butyl ester, 4-[4-(4-hydroxybutyloxy)benzoyl]Cinnamic acid tertiary butyl ester, 4-[4-(3-hydroxypropyloxy)benzoyl] Cinnamic acid tertiary Butyl ester, 4-[4-(2-hydroxyethyloxy)benzoyl] cinnamic acid tertiary butyl ester, 4-[ 4-hydroxymethyloxybenzoyl] cinnamic acid tertiary butyl ester, 4-[4-(8-hydroxyoctyloxy)benzoyl] cinnamic acid phenyl ester, 4-[4-(6-hydroxyhexyloxy)benzoyl] cinnamic acid Phenyl ester, 4-[4-(4-hydroxybutyloxy)benzoyl] phenyl cinnamic acid, 4-[4-(3-hydroxypropyloxy) benzoyl] phenyl cinnamic acid, 4-[4-(2-hydroxyl) Roxyethyloxy)benzoyl] phenyl cinnamic acid, 4-[4-hydroxymethyloxybenzoyl] phenyl cinnamic acid, 4-[4-hydroxybenzoyl] phenyl cinnamic acid, 4-[4-(8-hydroxyoctyloxy] )Benzoyl]cinnamic acid biphenyl ester, 4-[4-(6-hydroxyhexyloxy)benzoyl] cinnamic acid biphenyl ester, 4-[4-(4-hydroxybutyloxy)benzoyl] cinnamic acid biphenyl ester, 4 -[4-(3-hydroxypropyloxy)benzoyl] cinnamic acid biphenyl ester, 4-[4-(2-hydroxyethyloxy) benzoyl] cinnamic acid biphenyl ester, 4-[4-hydroxymethyloxybenzoyl] Cinnamic acid biphenyl ester, 4-[4-hydroxybenzoyl] cinnamic acid biphenyl ester, 4-benzoyl cinnamic acid 8-hydroxyoctyl ester, 4-benzoyl cinnamic acid 6-hydroxyhexyl ester, 4-benzoyl cinnamic acid 4-hydroxybutyl Ester, 4-benzoyl cinnamic acid 3-hydroxypropyl ester, 4-benzoyl cinnamic acid 2-hydroxyethyl ester, 4-benzoyl cinnamic acid hydroxymethyl ester, 4-[4-(8-hydroxyoctyloxy)benzoyl]chalcone, 4-[4-(6-hydroxyhexyloxy)benzoyl]chalcone, 4-[4-(4-hydroxybutyloxy)benzoyl]chalcone, 4-[4-(3-hydroxypropyloxy)benzoyl] Chalcone, 4-[4-(2-hydroxyethyloxy)benzoyl]chalcone, 4-(4-hydroxymethyloxybenzoyl)chalcone, 4-(4-hydroxybenzoyl)chalcone, 4'-[4-( 8-hydroxyoctyloxy)benzoyl]chalcone, 4'-[4-(6-hydroxyhexyloxy)benzoyl]chalcone, 4'-[4-(4-hydroxybutyloxy)benzoyl]chalcone, 4' -[4-(3-hydroxypropyloxy)benzoyl]chalcone, 4'-[4-(2-hydroxyethyloxy)benzoyl]chalcone, 4'-(4-hydroxymethyloxybenzoyl)chalcone, 4' -(4-hydroxybenzoyl)chalcone, etc. are mentioned.

(A) As a specific example of the compound which has a photo-alignment group and a carboxyl group which is a component, cinnamic acid, ferulic acid, 4-nitro cinnamic acid, 4-methoxy cinnamic acid, 3,4-dimethoxy cinnamic acid, coumarin-3-carboxylic acid And 4-(N,N-dimethylamino) cinnamic acid.

Specific examples of the compound having a photo-alignment group and an amino group as the component (A) include 4-amino cinnamic acid methyl ester, 4-amino cinnamic acid ethyl ester, 3-amino cinnamic acid methyl ester, and 3-amino cinnamic acid ethyl ester. I can.

(A) As a specific example of the compound which has a photo-alignment group and an alkoxysilyl group which is a component, 4-(3-trimethoxysilylpropyloxy) cinnamic acid methyl ester, 4-(3-triethoxysilylpropyloxy) methyl cinnamate Ester, 4-(3-trimethoxysilylpropyloxy) ethyl cinnamic ester, 4-(3-triethoxysilylpropyloxy) ethyl cinnamic acid ester, 4-(3-trimethoxysilylhexyloxy) cinnamic acid methyl ester , 4- (3-triethoxysilylhexyloxy) cinnamic acid methyl ester, 4- (3-trimethoxysilylhexyloxy) cinnamic acid ethyl ester and 4- (3-triethoxysilylhexyloxy) cinnamic acid ethyl Ester, etc. are mentioned.

The low molecular weight orientation component which is the component (A) may include the above specific examples, but is not limited thereto.

In addition, it is particularly preferable that the low-molecular alignment component which is the component (A) is a compound having a photo-alignment group and a hydroxy group. The compound having a photo-alignment group and a hydroxy group imparts photo-alignment to the cured film obtained from the cured film-forming composition of the present embodiment, and is used as an alignment material to improve adhesion with the layer of the polymerizable liquid crystal. Therefore, it becomes especially effective.

In addition, when the low-molecular alignment component (A) component is a compound having a photo-alignment group and a hydroxy group, as the component (A), a compound having two or more photo-alignment groups and/or two or more hydroxy groups is contained in the molecule. It is possible to use. Specifically, as component (A), a compound having two or more photo-alignment groups with one hydroxy group in the molecule, a compound having two or more hydroxy groups with one photo-alignment group in the molecule, or a photo-alignment in the molecule It is possible to use a compound each having two or more groups and hydroxy groups. For example, about a compound having two or more each of a photo-alignment group and a hydroxyl group in a molecule, a compound represented by the following formula can be illustrated.

[Formula 2]

By appropriately selecting such a compound, it becomes possible to control the molecular weight of the low molecular weight orientation component (A) component to a value within a desired range. In order to form the cured film of the present embodiment from the cured film-forming composition of the present embodiment, heat curing is required. When the heating is performed, the low molecular weight alignment component, which is the component (A), sublimes, and the molecular weight of the low molecular alignment component is adjusted. It can be suppressed by doing.

On the other hand, as the compound of the component (A) in the cured film forming composition of the present embodiment, it is a mixture of plural types of compounds having a photo-alignment group, a hydroxyl group, a carboxyl group, an amino group, and an alkoxysilyl group. May be.

[(B) component]

The component (B) contained in the cured film-forming composition of the present embodiment is a hydrophilic polymer.

In the cured film forming composition of the present embodiment, the polymer as the component (B) is preferably a polymer having a hydrophilic group such as a hydroxy group, a carboxyl group, or an amino group, and specifically, at least one of a hydroxy group and a carboxyl group. It can be made into a polymer (hereinafter, also referred to as a specific polymer).

(B) As a polymer which is a component, for example, acrylic polymer, polyamic acid, polyimide, polyvinyl alcohol, polyester, polyester polycarboxylic acid, polyether polyol, polyester polyol, polycarbonate polyol, polycaprolactone Polyols, polyalkyleneimines, polyallylamines, celluloses (cellulose or derivatives thereof), phenol novolak resins, polymers having a branched structure or a linear structure such as melamine formaldehyde resins, and cyclic polymers such as cyclodextrins. I can.

Among these, as the acrylic polymer, a polymer obtained by polymerizing a monomer having an unsaturated double bond such as acrylic acid ester, methacrylic acid ester, and styrene may be applied.

(B) As the specific polymer which is a component, Preferably, at least one of hydroxyalkylcyclodextrins, celluloses, polyethylene glycol ester groups and hydroxyalkyl ester groups having 2 to 5 carbon atoms, carboxyl group, and phenolic hydroxyl An acrylic polymer having at least one of the periods, an acrylic polymer having an aminoalkyl group in a side chain, a polyether polyol, a polyester polyol, a polycarbonate polyol, and a polycaprolactone polyol.

An acrylic polymer having at least one of a polyethylene glycol ester group and a hydroxyalkyl ester group having 2 to 5 carbon atoms, and at least one of a carboxyl group and a phenolic hydroxy group, which is a preferred example of the specific polymer of component (B), Although it may be an acrylic polymer having a structure, the skeleton of the main chain of the polymer constituting the acrylic polymer and the kind of side chains are not particularly limited.

As a structural unit having at least one of the above-described polyethylene glycol ester group and a hydroxyalkyl ester group having 2 to 5 carbon atoms, a preferable structural unit is represented by the following formula [B1].

As the structural unit having at least one of the above-described carboxyl group and phenolic hydroxy group, a preferable structural unit is represented by the following formula [B2].

[Formula 3]

In the above formulas [B1] and [B2], X ³ and X ⁴ each independently represent a hydrogen atom or a methyl group, and Y ¹ is an H-(OCH ₂ CH ₂ )n- group (where n is 2 To 50, preferably 2 to 10.) or a hydroxyalkyl group having 2 to 5 carbon atoms, and Y ² represents a carboxyl group or a phenolic hydroxy group.

The acrylic polymer which is an example of the component (B) preferably has a weight average molecular weight of 3000 to 200000, more preferably 4000 to 150000, and still more preferably 5000 to 100000. If the weight average molecular weight exceeds 200000 and is too large, the solubility in the solvent decreases and the handling property may decrease.If the weight average molecular weight is too small, such as less than 3000, the hardening is insufficient during thermal curing, resulting in solvent resistance and heat resistance. This may decrease. On the other hand, the weight average molecular weight is a value obtained by gel permeation chromatography (GPC) using polystyrene as standard data. Hereinafter, it is the same in this specification.

In the synthesis method of the acrylic polymer which is an example of the component (B), a monomer having at least one of a polyethylene glycol ester group and a hydroxyalkyl ester group having 2 to 5 carbon atoms (hereinafter, also referred to as a b1 monomer), a carboxyl group and a phenolic A method of copolymerizing a monomer having at least one of the hydroxy groups (hereinafter, also referred to as b2 monomer) is simple.

As the monomer having the above-described polyethylene glycol ester group, a monoacrylate or monomethacrylate of H-(OCH ₂ CH ₂ )n-OH is mentioned. The value of n is 2 to 50, preferably 2 to 10.

As a monomer having the above-described hydroxyalkyl ester group having 2 to 5 carbon atoms, for example, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl methacrylate, 2 -Hydroxypropyl acrylate, 4-hydroxybutyl acrylate, and 4-hydroxybutyl methacrylate are mentioned.

As a monomer which has a carboxyl group mentioned above, acrylic acid, methacrylic acid, and vinylbenzoic acid are mentioned, for example.

Examples of the monomer having a phenolic hydroxy group described above include p-hydroxystyrene, m-hydroxystyrene, and o-hydroxystyrene.

In addition, in the present embodiment, in synthesizing an acrylic polymer that is an example of component (B), monomers other than the b1 monomer and b2 monomer, specifically, a hydroxy group and a carboxyl group, are prepared as long as the effect of the present invention is not impaired. A monomer which does not have all can be used together.

As the monomer, for example, acrylic acid ester compounds such as methyl acrylate, ethyl acrylate, propyl acrylate, isopropyl acrylate, butyl methacrylate, butyl acrylate, isobutyl acrylate and t-butyl acrylate , Methyl methacrylate, ethyl methacrylate, propyl methacrylate, isopropyl methacrylate, isobutyl methacrylate and methacrylic acid ester compounds such as t-butyl methacrylate, maleimide, N-methyl maleimide , Maleimide compounds such as N-phenylmaleimide and N-cyclohexylmaleimide, acrylamide compounds, acrylonitrile, maleic anhydride, styrene compounds, and vinyl compounds.

The amount of the b1 monomer and b2 monomer used to obtain the acrylic polymer as an example of the component (B) is based on the total amount of all monomers used to obtain the acrylic polymer as the component (B), and the amount of the b1 monomer is 2 to 95 mol%. It is preferable that the b2 monomer is 5 mol% to 98 mol%.

When a monomer having only a carboxyl group is used as the b2 monomer, based on the total amount of all monomers used to obtain the acrylic polymer as component (B), the b1 monomer is 60 mol% to 95 mol%, and the b2 monomer is 5 mol% to 40 mol. It is preferably %.

On the other hand, when a monomer having only a phenolic hydroxy group is used as the b2 monomer, it is preferable that the b1 monomer is 2 mol% to 80 mol% and the b2 monomer is 20 mol% to 98 mol%. When the b2 monomer is too small than 20 mol%, the liquid crystal orientation of the resulting cured film is liable to be insufficient, and when it is too large than 98 mol%, the compatibility of the component (A) with the low molecular orientation component tends to decrease.

The method of obtaining the acrylic polymer, which is an example of the polymer of the component (B), is not particularly limited, but, for example, in a solvent in which a b1 monomer and a b2 monomer, a monomer other than the b1 and b2 monomers, and a polymerization initiator are coexisted, if necessary. , Obtained by polymerization reaction at a temperature of 50°C to 110°C. In this case, the solvent used is not particularly limited as long as it dissolves a monomer other than the b1 monomer and the b2 monomer, and the b1 monomer and b2 monomer used as necessary, and a polymerization initiator. As a specific example, it describes in the section of [solvent] mentioned later.

The acrylic polymer having an aminoalkyl group in the side chain, which is a preferred example of the specific polymer of the component (B), is, for example, aminoalkyl such as aminoethyl acrylate, aminoethyl methacrylate, aminopropyl acrylate and aminopropyl methacrylate. The one obtained by polymerizing the ester monomer, or the one obtained by copolymerizing the aminoalkyl ester monomer and one or two or more monomers selected from the above acrylic monomers can be mentioned.

The acrylic polymer which is an example of the polymer of the component (B) obtained by the above method is usually in a state of a solution dissolved in a solvent.

In addition, a solution of an acrylic polymer, which is an example of the polymer of component (B) obtained by the above method, was added to diethyl ether or water under stirring to reprecipitate, and the resulting precipitate was filtered and washed, and then under normal pressure or reduced pressure, at room temperature. It can be dried or heat-dried to obtain an acrylic polymer powder which is an example of the component (B). By the above-described operation, the polymerization initiator and unreacted monomer coexisting with the acrylic polymer as an example of the component (B) can be removed, and as a result, powder of the acrylic polymer as an example of the purified component (B) is obtained. When it is not possible to sufficiently purify in one operation, the obtained powder may be re-dissolved in a solvent, and the above-described operation may be repeated.

Next, as the polyether polyol, which is a preferred example of the specific polymer of component (B), polyhydric alcohols such as polyethylene glycol, polypropylene glycol, propylene glycol or bisphenol A, triethylene glycol and sorbitol are added to propylene oxide, polyethylene glycol, and polyol. What added propylene glycol etc. is mentioned. Specific examples of polyether polyols include ADEKA Cororation ADEKA POLYETHER P series, G series, EDP series, BPX series, FC series, CM series, NOF Corporation UNIOX (registered trademark) HC-40, HC-60, ST-30E , ST-40E, G-450, G-750, UNIOL (registered trademark) TG-330, TG-1000, TG-3000, TG-4000, HS-1600D, DA-400, DA-700, DB-400, NONION (registered trademark) LT-221, ST-221, OT-221, etc. are mentioned.

(B) As a polyester polyol which is a preferred example of the specific polymer of the component, ethylene glycol, propylene glycol, butylene glycol, diethylene glycol, polyethylene glycol, and polyvalent carboxylic acids such as adipic acid, sebacic acid and isophthalic acid. What made a diol, such as propylene glycol, react is mentioned. As a specific example of a polyester polyol, DIC corporation POLYLITE (registered trademark) OD-X-286, OD-X-102, OD-X-355, OD-X-2330, OD-X-240, OD-X- 668, OD-X-2108, OD-X-2376, OD-X-2044, OD-X-688, OD-X-2068, OD-X-2547, OD-X-2420, OD-X-2523, OD-X-2555, OD-X-2560, Kuraray Co., Ltd. POLYOL P-510, P-1010, P-2010, P-3010, P-4010, P-5010, P-6010, F- 510, F-1010, F-2010, F-3010, P-1011, P-2011, P-2013, P-2030, N-2010, PNNA-2016, and the like.

As polycaprolactone polyol which is a preferable example of the specific polymer of (B) component, polyhydric alcohols, such as trimethylolpropane and ethylene glycol, as an initiator, ring-opening polymerization of ε-caprolactone are mentioned. Specific examples of the polycaprolactone polyol include DIC Corporation's POLYLITE (registered trademark) OD-X-2155, OD-X-640, OD-X-2568, Daicel Chemical Industries, Ltd. PLACCEL (registered trademark) 205, L205AL. , 205U, 208, 210, 212, L212AL, 220, 230, 240, 303, 305, 308, 312, 320, and the like.

As a polycarbonate polyol which is a preferable example of the specific polymer of (B) component, what made polyhydric alcohol, such as trimethylolpropane and ethylene glycol, react with diethyl carbonate, diphenyl carbonate, ethylene carbonate, etc. are mentioned. Specific examples of polycarbonate polyols include PLACCEL (registered trademark) CD205, CD205PL, CD210, CD220, C-590, C-1050, C-2050, C- manufactured by Daicel Chemical Industries, Ltd., manufactured by Kuraray Co., Ltd. 2090, C-3090, etc. are mentioned.

As cellulose which is a preferred example of the specific polymer of the component (B), hydroxyalkyl celluloses such as hydroxyethylcellulose and hydroxypropylcellulose, hydroxyethylmethylcellulose, hydroxypropylmethylcellulose, and hydroxyethylethylcellulose, etc. Hydroxyalkylalkyl celluloses and celluloses, for example, hydroxyalkyl celluloses such as hydroxyethyl cellulose and hydroxypropyl cellulose are preferable.

Cyclodextrins that are preferred examples of the specific polymer of component (B) include cyclodextrins such as α-cyclodextrin, β-cyclodextrin and γ cyclodextrin, methyl-α-cyclodextrin, methyl-β-cyclodextrin and methyl- methylated cyclodextrins such as γ-cyclodextrin, and hydroxymethyl-α-cyclodextrin, hydroxymethyl-β-cyclodextrin, hydroxymethyl-γ-cyclodextrin, 2-hydroxyethyl-α-cyclodextrin, 2 -Hydroxyethyl-β-cyclodextrin, 2-hydroxyethyl-γ-cyclodextrin, 2-hydroxypropyl-α-cyclodextrin, 2-hydroxypropyl-β-cyclodextrin, 2-hydroxypropyl-γ -Cyclodextrin, 3-hydroxypropyl-α-cyclodextrin, 3-hydroxypropyl-β-cyclodextrin, 3-hydroxypropyl-γ-cyclodextrin, 2,3-dihydroxypropyl-α-cyclodextrin , Hydroxyalkylcyclodextrins such as 2,3-dihydroxypropyl-β-cyclodextrin and 2,3-dihydroxypropyl-γ-cyclodextrin, and the like.

As melamine formaldehyde resin which is a preferable example of the specific polymer of (B) component, resin etc. represented by the following formula, such as a resin obtained by polycondensing melamine and formaldehyde, etc. are mentioned.

[Formula 4]

In the above formula, R ²¹ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and n is a natural number representing the number of repeating units.

It is preferable that the melamine formaldehyde resin of the component (B) is alkylated with a methylol group generated during polycondensation of melamine and formaldehyde from the viewpoint of storage stability.

The method of obtaining the melamine formaldehyde resin of component (B) is not particularly limited, but in general, it is synthesized by mixing melamine and formaldehyde, making it weakly alkaline using sodium carbonate or ammonia, and heating at 60 to 100°C. do. The methylol group can be alkoxylated by reacting the resin obtained again with alcohol.

The melamine formaldehyde resin of the component (B) preferably has a weight average molecular weight of 250 to 5000, more preferably 300 to 4000, and still more preferably 350 to 3500. If the weight average molecular weight exceeds 5000 and is too large, the solubility in the solvent is lowered and the handling property is lowered.If the weight average molecular weight is too small, such as less than 250, the hardening is insufficient during thermal curing, resulting in solvent resistance and heat resistance. There are cases where the improvement effect of

In the embodiment of the present invention, the melamine formaldehyde resin of component (B) may be used in a liquid form or in a solution form obtained by re-dissolving the purified liquid in a solvent described later.

In addition, in the embodiment of the present invention, the melamine formaldehyde resin of the component (B) may be a mixture of a plurality of types of melamine formaldehyde resins of the component (B).

As a phenol novolak resin which is a preferable example of the specific polymer of (B) component, a phenol-formaldehyde polycondensate etc. are mentioned, for example.

In the cured film forming composition of the present embodiment, the polymer of the component (B) may be used in the form of a powder or in the form of a solution in which the purified powder is redissolved in a solvent to be described later.

In addition, in the cured film formation composition of this embodiment, the (B) component may be a mixture of plural kinds of polymers exemplified as the (B) component.

As described above, the cured film forming composition of the present embodiment of the present invention is constituted by containing a polymer having at least one of (A) a photo-alignment group and a hydroxy group, and (B) a hydroxy group and a carboxyl group. In the compound as a component (A), the photo-alignment group constitutes a hydrophobic photoreactive portion, and the hydroxy group constitutes a hydrophilic thermal reaction portion. The polymer of the component (B) has at least one of a hydroxy group and a carboxyl group as described above.

Therefore, the cured film formed from the cured film-forming composition of the present embodiment is formed so that the film structure is stabilized, due to the property of the component (B), and the inside thereof becomes hydrophilic. And the compound of the component (A) in the cured film is unevenly distributed in the vicinity of the surface of the cured film. More specifically, the compound of the component (A) is unevenly distributed in the vicinity of the surface of the cured film while taking a structure in which the hydrophilic thermal reaction portion faces the inner side of the cured film and the hydrophobic photo reaction portion faces the surface side. As a result, the cured film of the present embodiment realizes a structure in which the ratio of the photoreactive groups of the component (A) present in the vicinity of the surface is increased. And, when the cured film of this embodiment is used as an alignment material, it can improve the efficiency of the photoreaction for photo-alignment, and can have excellent orientation sensitivity. Furthermore, the cured film-forming composition of the present embodiment becomes an orientation material suitable for formation of a patterned retardation material, and a patterned retardation material produced by using the cured film-forming composition can have excellent pattern formation.

In addition, the cured film formation composition of this embodiment can contain a crosslinking agent as (D) component as mentioned above. Accordingly, in the interior of the cured film obtained from the cured film-forming composition of the present embodiment, a crosslinking reaction by thermal reaction using a crosslinking agent (D) can be performed before the photoreaction of the compound of component (A) by the photo-alignment group. As a result, when this cured film is used as an alignment material, the polymerizable liquid crystal applied on the alignment material and resistance to the solvent can be improved.

And the cured film forming composition of this embodiment of the present invention, together with the component (A) and the component (B), as the component (C), having a hydroxyl group and a (meth)acrylic group other than the component (A) Contains compounds. When the cured film obtained from the cured film forming composition of the present embodiment is used as an alignment material, the compound as the component (C) functions to enhance the adhesion between the layers of the cured polymerizable liquid crystal formed thereon. Next, the component (C) contained in the cured film forming composition of the present embodiment will be described.

[(C) ingredient]

The component (C) contained in the cured film forming composition of the present embodiment is a compound having a hydroxyl group and a (meth)acrylic group other than the component (A).

It is preferable that the compound of (C) component has one or more hydroxyl groups and one (meth)acryl group.

When the cured film formed from the cured film forming composition of the present embodiment containing the component (C) is used as an alignment material, so that the adhesion between the alignment material and the layer of the polymerizable liquid crystal is improved, the polymerizable functional group of the polymerizable liquid crystal and the alignment material are Crosslinking reaction sites can be linked by covalent bonds. As a result, the retardation material of this embodiment obtained by laminating a cured polymerizable liquid crystal on the alignment material of this embodiment can maintain strong adhesion even under conditions of high temperature and high humidity, and can exhibit high durability against peeling, etc. .

The content of the component (C) in the cured film forming composition of the embodiment of the present invention is preferably 0.1 to 40 parts by mass based on 100 parts by mass of the total amount of the compound as the component (A) and the polymer of the component (B). It is a mass part, More preferably, it is 5 mass parts-35 mass parts. By setting the content of the component (C) to 0.1 parts by mass or more, sufficient adhesion can be provided to the formed cured film. However, when it is more than 40 parts by mass, the storage stability of the cured film-forming composition may decrease.

In addition, in the cured film formation composition of this embodiment, (C) component may be a mixture of multiple types of the compound of (C) component.

Below, a preferable example of the compound of (C) component is given. In addition, the compound of (C) component is not limited to the following compound examples.

[Formula 5]

(In the above formula, R ¹¹ represents a hydrogen atom or a methyl group, and m represents an integer of 1 to 10.)

[(D) ingredient]

The cured film formation composition of this embodiment can contain a crosslinking agent as (D) component.

More specifically, (D) component reacts with the compound of component (A), the polymer of component (B) and the compound of component (C) described above, and is lower than the sublimation temperature of the compound of component (A). It is a crosslinking agent that reacts in. The crosslinking agent of the (D) component is at a lower temperature than the sublimation temperature of the compound of the component (A), the hydroxyl group of the compound as the component (A), the hydroxyl group and/or carboxyl group contained in the polymer as the component (B), ( C) It binds to the hydroxy group of the compound which is a component. As a result, as described later, when the compound of the component (A), the polymer of the component (B) and the compound of the component (C) and the crosslinking agent that is the component (D) react thermally, the compound of the component (A) sublimates. It can be suppressed from becoming. And the cured film forming composition of this embodiment can form an alignment material with high photoreaction efficiency as mentioned above as a cured film.

And in the cured film formation composition of this embodiment, it is preferable that the crosslinking agent of (D) component is hydrophilic. When forming a cured film using the cured film forming composition of the present embodiment, it is to suitably disperse the crosslinking agent of the component (D) in the film.

Although compounds such as an epoxy compound, a methylol compound, and an isocyanate compound are mentioned as a crosslinking agent which is a component (D), Preferably it is a methylol compound.

As a specific example of the above-mentioned methylol compound, compounds, such as alkoxy methylation glycoluril, alkoxy methylation benzoguanamine, and alkoxy methylation melamine, are mentioned, for example.

As specific examples of the alkoxymethylated glycoluril described above, for example, 1,3,4,6-tetrakis (methoxymethyl) glycoluril, 1,3,4,6-tetrakis (butoxymethyl) Glycoluril, 1,3,4,6-tetrakis (hydroxymethyl) glycoluril, 1,3-bis (hydroxymethyl) urea, 1,1,3,3-tetrakis (butoxymethyl) urea, 1,1,3,3-tetrakis(methoxymethyl)urea, 1,3-bis(hydroxymethyl)-4,5-dihydroxy-2-imidazolinone, and 1,3-bis( Methoxymethyl)-4,5-dimethoxy-2-imidazolinone, etc. are mentioned. As commercial products, Mitsui Cytec Ltd. made glycoluril compound (trade name: CYMEL (registered trademark) 1170, POWDERLINK (registered trademark) 1174), and other compounds, methylated urea resin (trade name: UFR (registered trademark) 65), butylated urea resin (Brand name: UFR (registered trademark) 300, U-VAN10S60, U-VAN10R, U-VAN11HV), urea/formaldehyde resin (high condensation type, brand name: BECKMINE (registered trademark) J-300S, copper ( Same) P-955, the same N), etc. are mentioned.

As a specific example of the alkoxymethylated benzoguanamine mentioned above, tetramethoxymethylbenzoguanamine etc. are mentioned, for example. As a commercial item, Mitsui Cytec Ltd. product (brand name: CYMEL (registered trademark) 1123), Sanwa Chemical Co., Ltd. product (brand name: NIKALAC (registered trademark) BX-4000, copper BX-37, copper BL-60, copper BX-55H) etc. are mentioned.

As a specific example of the alkoxymethylated melamine mentioned above, hexamethoxymethylmelamine etc. are mentioned, for example. As a commercial item, Mitsui Cytec Ltd. methoxymethyl type melamine compound (trade name: CYMEL (registered trademark) 300, copper 301, copper 303, copper 350), butoxymethyl type melamine compound (trade name: MYCOAT (registered trademark) 506, 508), a methoxymethyl melamine compound (trade name: NIKALAC (registered trademark) MW-30, MW-22, MW-11, MS-001, MX-002, manufactured by Sanwa Chemical Co., Ltd.) MX-730, MX-750, MX-035), butoxymethyl-type melamine compound (trade name: NIKALAC (registered trademark) MX-45, MX-410, MX-302), etc. are mentioned.

Further, it may be a compound obtained by condensing a melamine compound, a urea compound, a glycoluril compound and a benzoguanamine compound in which the hydrogen atom of such an amino group is substituted with a methylol group or an alkoxymethyl group. For example, a high molecular weight compound prepared from a melamine compound and a benzoguanamine compound described in US Patent No. 6323310 may be mentioned. As a commercial item of the said melamine compound, a brand name: CYMEL (registered trademark) 303 (manufactured by Mitsui Cytec Ltd.) may be mentioned, and as a commercial item of the benzoguanamine compound, a brand name: CYMEL (registered trademark) 1123 (Mitsui Cytec Ltd.), etc. are mentioned.

Further, as the component (D), a hydroxymethyl group or an alkoxymethyl group such as N-hydroxymethylacrylamide, N-methoxymethylmethacrylamide, N-ethoxymethylacrylamide and N-butoxymethylmethacrylamide A polymer prepared using an acrylamide compound or a methacrylamide compound substituted with may also be used.

Examples of the polymer include poly(N-butoxymethylacrylamide), a copolymer of N-butoxymethylacrylamide and styrene, a copolymer of N-hydroxymethylmethacrylamide and methylmethacrylate, A copolymer of N-ethoxymethyl methacrylamide and benzyl methacrylate, and a copolymer of N-butoxymethylacrylamide, benzyl methacrylate and 2-hydroxypropyl methacrylate, and the like. The weight average molecular weight of such a polymer is 1000 to 500000, preferably 2000 to 200000, more preferably 3000 to 150000, still more preferably 3000 to 50000.

These crosslinking agents can be used alone or in combination of two or more.

The content of the crosslinking agent of the component (D) in the cured film forming composition of the present embodiment is 10 parts by mass to 100 parts by mass based on 100 parts by mass of the total amount of the compound as the component (A) and the polymer of the component (B). It is preferable, and more preferably, it is 15 mass parts-80 mass parts. When the content of the crosslinking agent is too small than 10 parts by mass, the solvent resistance and heat resistance of the cured film obtained from the cured film-forming composition decrease, and the orientation sensitivity at the time of photo-alignment decreases. On the other hand, when the content is too large than 100 parts by mass, the photo-alignment property and storage stability may decrease.

[(E) component]

In addition to the component (A), the component (B) and the component (C), the cured film forming composition of the present embodiment may contain the component (D) described above, and further, (E) It may contain a crosslinking catalyst as a component.

(E) As a crosslinking catalyst which is a component, it can be set as an acid or a thermal acid generator, for example. This component (E) becomes effective for accelerating a thermosetting reaction in formation of a cured film using the cured film forming composition of the present embodiment.

When an acid or a thermal acid generator is used as the component (E), the component (E) is a compound containing a sulfonic acid group, hydrochloric acid or a salt thereof, a compound that thermally decomposes during pre-baking or post-baking to generate an acid, that is, a temperature of 80°C to It is not particularly limited as long as it is a compound that generates an acid by thermal decomposition at 250°C.

Such compounds include, for example, hydrochloric acid, methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid, butanesulfonic acid, pentanesulfonic acid, octanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, camphorsulfonic acid, tri Fluoromethanesulfonic acid, p-phenolsulfonic acid, 2-naphthalenesulfonic acid, mesitylenesulfonic acid, p-xylene-2-sulfonic acid, m-xylene-2-sulfonic acid, 4-ethylbenzenesulfonic acid, 1H,1H,2H,2H-perfluorooctanesulfonic acid, perfluoro(2-ethoxyethane)sulfonic acid, pentafluoroethanesulfonic acid, nonafluorobutane-1-sulfonic acid, dodecylbenzenesulfonic acid Sulfonic acids such as, or hydrates and salts thereof.

In addition, as a compound that generates an acid by heat, for example, bis(tosyloxy)ethane, bis(tosyloxy)propane, bis(tosyloxy)butane, p-nitrobenzyltosylate, o-nitrobenzyltosylate , 1,2,3-phenylene tris (methylsulfonate), p-toluenesulfonic acid pyridinium salt, p-toluenesulfonic acid morpholinium salt, p-toluenesulfonic acid ethyl ester, p-toluenesulfonic acid propyl ester, p- Toluenesulfonic acid butyl ester, p-toluenesulfonic acid isobutyl ester, p-toluenesulfonic acid methyl ester, p-toluenesulfonic acid phenethyl ester, cyanomethylp-toluenesulfonate, 2,2,2-trifluoroethyl p-toluenesulfonate, 2-hydroxybutyl p-tosylate, N-ethyl-4-toluenesulfonamide, and compounds represented by the following formulas [PAG-1] to [PAG-41], and the like. .

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

The content of the crosslinking catalyst of the component (E) in the cured film forming composition of the embodiment of the present invention is preferably 0.01 mass per 100 parts by mass of the total amount of the compound as the component (A) and the polymer of the component (B). It is a part by mass to 10 mass parts, More preferably, it is 0.05 mass part to 8 mass parts, More preferably, it is 0.1 mass part to 6 mass parts. By setting the content of the component (E) to 0.01 parts by mass or more, sufficient thermosetting and solvent resistance can be provided to the cured film of the embodiment of the present invention, and high sensitivity to exposure light can also be provided. In addition, the storage stability of the cured film-forming composition can be improved by making the content of the component (E) 10 parts by mass or less.

[Other additives]

The cured film-forming composition of the embodiment of the present invention may contain other additives as long as the effects of the present invention are not impaired.

Other additives may contain, for example, a sensitizer. The sensitizer becomes effective in accelerating the photoreaction when forming the cured film of the embodiment of the present invention from the cured film forming composition of the present embodiment.

Examples of the sensitizer include derivatives such as benzophenone, anthracene, anthraquinone and thioxanthone, and a nitrophenyl compound. Among these, N,N-diethylaminobenzophenone, a derivative of benzophenone, and 2-nitrofluorene, 2-nitrofluorenone, 5-nitroacenaphthene, 4-nitrobiphenyl, 4-nitrocinic acid, 4 Particularly preferred are nitrostilbene, 4-nitrobenzophenone and 5-nitroindole.

These sensitizers are not particularly limited to those described above. These can be used alone or in combination of two or more kinds of compounds.

In the embodiment of the present invention, the ratio of use of the sensitizer is preferably 0.1 parts by mass to 20 parts by mass, and more preferably 0.2 parts by mass to 10 parts by mass based on 100 parts by mass of the component (A). When this ratio is too small, the effect as a sensitizer may not be sufficiently obtained, and when this ratio is too large, the transmittance of the formed cured film may decrease or the coating film may become rough.

In addition, the cured film forming composition of the embodiment of the present invention, as other additives, as long as the effect of the present invention is not impaired, a silane coupling agent, a surfactant, a rheology modifier, a pigment, a dye, a storage stabilizer, an antifoaming agent, an antioxidant. And the like.

[solvent]

The cured film-forming composition of the embodiment of the present invention is often used in a solution state dissolved in a solvent. The solvent used at this time is one that dissolves (A) component, (B) component and (C) component, if necessary, (D) component, (E) component, and/or other additives, and has such a solubility If it is a solvent, the kind and structure, etc. are not specifically limited.

Specific examples of the solvent, for example, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene Glycol, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol propyl ether acetate, toluene, xylene, methyl ethyl ketone, cyclopentanone, cyclohexanone, 2-butanone, 3-methyl-2-penta Non, 2-pentanone, 2-heptanone, γ-butyrolactone, 2-hydroxy ethyl propionate, 2-hydroxy-2-methyl ethyl propionate, ethyl ethoxy acetate, ethyl hydroxy acetate, 2-hydroxy -3-methylbutanoate, 3-methoxy methyl propionate, 3-methoxy ethyl propionate, 3-ethoxy ethyl propionate, 3-ethoxy methyl propionate, methyl pyruvate, ethyl pyruvate, ethyl acetate, butyl acetate, ethyl lactate , Butyl lactate, N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

These solvents can be used alone or in combination of two or more. Among these solvents, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, cyclohexanone, 2-heptanone, propylene glycol propyl ether, propylene glycol propyl ether acetate, ethyl lactate, butyl lactate, 3-methoxy methyl propionate, Ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, and methyl 3-ethoxypropionate are more preferable because film-forming properties are good and safety is high.

<Preparation of cured film forming composition>

The cured film forming composition of the embodiment of the present invention is a thermosetting cured film forming composition having photo-alignment. As described above, the cured film forming composition of the present embodiment is a polymer having at least one of a hydroxy group and a carboxyl group as a component (A), a low molecular orientation component as a component (B), and a (C) component as a ( It contains the compound which has a hydroxyl group and a (meth)acrylic group other than the A) component. Furthermore, a crosslinking agent can be contained as a component (D), and a crosslinking catalyst can be contained as a component (E). And, as long as the effect of the present invention is not impaired, other additives may be contained, and further, a solvent may be contained.

The mixing ratio of the component (A) and the component (B) is preferably 5:95 to 60:40 in terms of mass ratio. When the content of the component (B) is too large, the liquid crystal orientation tends to decrease, and when the content is too small, the orientation property tends to decrease as the solvent resistance decreases.

Preferred examples of the cured film forming composition of the present embodiment are as follows.

[1]: The blending ratio of the component (A) and the component (B) is 5:95 to 60:40 by mass, and 0.1 to 40 parts by mass based on 100 parts by mass of the total amount of the component (A) and the component (B) A cured film forming composition containing the component (C) in parts by mass.

[1]: The blending ratio of the component (A) and the component (B) is 5:95 to 60:40 by mass, and 0.1 to 40 parts by mass based on 100 parts by mass of the total amount of the component (A) and the component (B) A cured film-forming composition containing the component (C) and a solvent in parts by mass.

[1]: The blending ratio of the component (A) and the component (B) is 5:95 to 60:40 by mass, and 0.1 to 40 parts by mass based on 100 parts by mass of the total amount of the component (A) and the component (B) A cured film-forming composition containing a component (C), a component (D) of 10 parts by mass to 100 parts by mass, and a solvent.

[1]: The blending ratio of the component (A) and the component (B) is 5:95 to 60:40 by mass, and 0.1 to 40 parts by mass based on 100 parts by mass of the total amount of the component (A) and the component (B) A cured film-forming composition containing (C) component, 10 mass parts-100 mass parts (D) component, 0.01 mass parts-10 mass parts (E) component, and a solvent in mass parts.

In the case of using the cured film forming composition of the present embodiment as a solution, the mixing ratio, preparation method, etc. will be described in detail below.

The ratio of the solid content in the cured film forming composition of the present embodiment is not particularly limited as long as each component is uniformly dissolved in the solvent, but is 1% by mass to 80% by mass, and preferably 3% by mass to 60% by mass. It is mass %, More preferably, it is 5 mass%-40 mass %. Here, the solid content refers to the thing excluding the solvent from all components of the cured film-forming composition.

The preparation method of the cured film-forming composition of this embodiment is not specifically limited. As a preparation method, for example, in a solution obtained by dissolving the component (B) in a solvent, the component (A) and the component (C), furthermore, the component (D) and the component (E) are mixed in a predetermined ratio. , A method of obtaining a homogeneous solution, or a method of adding and mixing other additives as necessary at an appropriate stage of this preparation method.

In preparation of the cured film forming composition of the present embodiment, a solution of a specific copolymer obtained by polymerization reaction in a solvent can be used as it is. In this case, for example, by copolymerizing at least one of a monomer having a polyethylene glycol ester group and a monomer having a hydroxyalkyl ester group having 2 to 5 carbon atoms, and at least one of a monomer having a carboxyl group and a monomer having a phenolic hydroxy group To the solution of the component (B) to be obtained, in the same manner as described above, the component (A) and the component (C), further, the component (D), and the component (E) are added to obtain a uniform solution. At this time, an additional solvent may be added for the purpose of concentration adjustment. At this time, the solvent used in the process of producing the component (B) and the solvent used for adjusting the concentration of the cured film-forming composition may be the same or may be different.

In addition, it is preferable to use the solution of the prepared cured film-forming composition after filtering with a filter or the like having a pore diameter of about 0.2 μm.

<Cured film, alignment material and retardation material>

The solution of the cured film forming composition of this embodiment is applied to a substrate (e.g., a silicon/silicon dioxide coated substrate, a silicon nitride substrate, a metal such as aluminum, molybdenum, chromium, etc. coated substrate, a glass substrate, Quartz substrate, ITO substrate, etc.) or films (e.g., triacetyl cellulose (TAC) film, cycloolefin polymer film, polyethylene terephthalate film, resin film such as acrylic film), etc., bar coat, rotation coating, spilling A cured film can be formed by coating, roll coating, slit coating, slit followed by rotational coating, inkjet coating, printing, or the like to form a coating film, followed by heating and drying in a hot plate or an oven.

As the conditions for heat drying, the curing reaction may proceed to such an extent that the component of the alignment material formed from the cured film does not elute in the polymerizable liquid crystal solution applied thereon. For example, a temperature of 60°C to 200°C, a time of 0.4 A heating temperature and heating time suitably selected within the range of minutes to 60 minutes are employed. The heating temperature and heating time are preferably 70°C to 160°C and 0.5 minutes to 10 minutes.

The film thickness of the cured film formed by using the curable composition of the present embodiment is, for example, 0.05 μm to 5 μm, and it can be appropriately selected in consideration of the step difference of the substrate to be used and optical and electrical properties.

The thus formed cured film can function as a member for aligning an alignment material, that is, a compound having liquid crystal properties including a polymerizable liquid crystal or the like by performing polarized UV irradiation.

As the irradiation method of polarized UV, ultraviolet light or visible light having a wavelength of 150 nm to 450 nm is usually used, but it is performed by irradiating linearly polarized light from a vertical or oblique direction at room temperature or in a heated state.

Since the alignment material formed from the cured film composition of the present embodiment has solvent resistance and heat resistance, a retardation material made of a polymerizable liquid crystal solution is applied on the alignment material and then heated to a phase transition temperature of the liquid crystal to prepare a retardation material. It is made into a liquid crystal state, and it aligns on an alignment material. Further, the retardation material having a desired orientation state is cured as it is, thereby forming a retardation material having a layer having optical anisotropy.

As the retardation material, for example, a liquid crystal monomer having a polymerizable group and a composition containing the same are used. And when the substrate on which the alignment material is formed is a film, the film having the retardation material of the present embodiment becomes useful as a retardation film. As a retardation material forming such a retardation material, there is a liquid crystal state and, on the alignment material, an orientation state such as horizontal orientation, cholesteric orientation, vertical orientation, and hybrid orientation is taken. Each retardation material is required It can be used separately according to the phase difference characteristics.

In addition, in the case of manufacturing a patterned retardation material used for a 3D display, from the cured film composition of the present embodiment to the cured film formed by the above method, from a predetermined standard through a mask of a line and space pattern, For example, polarized UV exposure is performed in the direction of +45 degrees, and then polarized UV is exposed in the direction of -45 degrees after separating the mask to form an alignment material in which two kinds of liquid crystal alignment regions having different orientation control directions of the liquid crystal are formed. . Thereafter, a retardation material composed of a polymerizable liquid crystal solution is applied and then heated to a phase transition temperature of the liquid crystal to make the retardation material a liquid crystal state. The polymerizable liquid crystal in a liquid crystal state is aligned on an alignment material in which two types of liquid crystal alignment regions are formed, and forms an alignment state corresponding to each liquid crystal alignment region. Then, the phase difference material in which such an orientation state is realized is hardened as it is, and the above-described orientation state is fixed, and a patterned phase difference material in which a plurality of two types of phase difference regions having different phase difference characteristics are arranged regularly can be obtained. .

In addition, the alignment material formed from the cured film composition of the present embodiment can also be used as a liquid crystal alignment film for a liquid crystal display device. For example, using two substrates formed as described above and having an alignment material of this embodiment, these substrates are bonded together so that the alignment materials on both substrates face each other through a spacer, and then liquid crystals between these substrates By injecting, a liquid crystal display device in which the liquid crystal is aligned can be manufactured.

Accordingly, the cured film forming composition of the present embodiment can be suitably used for manufacturing various retardation materials (phase difference films) and liquid crystal display devices.

Example

Hereinafter, an example is given and this embodiment is demonstrated in more detail. However, the present invention is not limited to these examples.

[Composition components used in Examples and their abbreviations]

Each composition component used in the following Examples and Comparative Examples is as follows.

<Compound having photo-alignment group and hydroxyl group>

CIN1: 4-(6-hydroxyhexyloxy) cinnamic acid methyl ester

[Formula 13]

CIN2: 3-methoxy-4- (6-hydroxyhexyloxy) cinnamic acid methyl ester

[Formula 14]

<Polymer having a hydroxyl group and a carboxyl group>

PEPO: Polyester polyol polymer (adipic acid/diethylene glycol copolymer having the following structural units. Molecular weight 4,800.)

[Formula 15]

(In the above formula, R represents alkylene.)

<crosslinking agent>

HMM: melamine crosslinking agent represented by the following structural formula

[Formula 16]

PBMAA: poly(N-butoxymethylacrylamide)

<crosslinking catalyst>

PTSA: paratoluenesulfonic acid

[Formula 17]

<Compound having a hydroxyl group and a (meth)acrylic group>

Compound C-1 having a hydroxy group and a (meth)acryl group:

[Formula 18]

Compound C-2 having a hydroxy group and a (meth)acryl group:

[Formula 19]

Compound C-3 having a hydroxy group and a (meth)acryl group:

[Formula 20]

<solvent>

Each cured film-forming composition of Examples and Comparative Examples contained a solvent, and propylene glycol monomethyl ether (PM-P) and ethyl acetate (AcEt) were used as the solvent.

<Examples and Comparative Examples>

(Synthesis Example 1) Synthesis of CIN11

(Synthesis Example 1-1) Synthesis of CIN11-1 precursor of CIN11

[Formula 21]

In a 1 L 4-neck flask, 80.0 g of 4-bromo-4'-hydroxybenzophenone, 500 mL of N,N-dimethylacetamide, 55.4 g of tert-butyl acrylate, 160.2 g of tributylamine, palladium acetate 1.29 g and 3.50 g of tri(o-tolyl)phosphine were added, followed by stirring while heating to 100°C. After completion of the reaction, the reaction system was poured into 2 L of ethyl acetate, and extraction was performed using 1N-hydrochloric acid aqueous solution and saturated brine. Anhydrous magnesium sulfate was added to the extracted organic layer, dehydrated and dried, and anhydrous magnesium sulfate was filtered. The obtained filtrate was solvent distilled off using a rotary evaporator, and 109.4 g of the target product CIN11-1 (red brown viscous body) was obtained. The obtained CIN11-1 was used for the next reaction without purification.

(Synthesis Example 1-2) Synthesis of CIN11

[Formula 22]

To a 2 L four-necked flask, 93.4 g of CIN11-1, 1 L of N,N-dimethylformamide, 39.3 g of 6-chloro-1-hexanol, 119.4 g of potassium carbonate, and 4.8 g of potassium iodide were added. The mixture was stirred while heating to 100°C. After completion of the reaction, the reaction system was poured into 5 L of water, neutralized with 1N-hydrochloric acid aqueous solution, and extracted using ethyl acetate. Anhydrous magnesium sulfate was added to the extracted organic layer, dehydrated and dried, and anhydrous magnesium sulfate was filtered. The obtained filtrate was subjected to solvent distillation using a rotary evaporator. The residue was recrystallized using isopropanol/hexane = 1/10 to obtain 113.8 g of CIN11 (ocher solid). The results measured by ¹ H-NMR as the target object are shown below. From this result, it was confirmed that the obtained solid was the target CIN11.

[Formula 23]

Polymer Synthesis Example 1

3.5 g of MAA, 7.0 g of MMA, 7.0 g of HEMA, and 0.5 g of AIBN (azobisisobutyronitrile) as a polymerization initiator were dissolved in 53.9 g of PM-P and reacted at 75° C. for 20 hours to obtain an acrylic copolymer solution (solid content concentration of 25 Mass%) was obtained (P-1). Mn of the obtained acrylic copolymer was 10,300 and Mw was 24,600.

<Examples and Comparative Examples>

Each cured film forming composition of Examples 1 to 6 and Comparative Examples 1 and 2 was prepared with the composition shown in Table 1. Next, each cured film forming composition was used to form a cured film, and for each of the obtained cured films, adhesion, orientation sensitivity, pattern formation property, and transmittance were evaluated.

[Table 1]

[Evaluation of adhesion]

After coating the cured film-forming composition of Examples 1 to 5 and Comparative Examples 1 and 2 using a bar coater on a TAC film, heating and drying in a heat circulation oven at a temperature of 110° C. for 120 seconds To form a cured film. This linearly polarized light of 313nm was irradiated perpendicularly to 20mJ / cm ² to 40mJ / cm ² in each hardened layer. On the cured film on the substrate after exposure, the polymerizable liquid crystal solution RMS03-013C for horizontal alignment manufactured by Merck Ltd. was applied using a spin coater, and then prebaked on a hot plate at 60°C for 60 seconds, and the film thickness A 1.0 μm coating film was formed. This film was exposed at 1000 mJ/cm ² , polymerizable liquid crystal was polymerized, and a retardation material was produced. A crosscut (1 mm x 1 mm x 100 cells) was put on the obtained retardation material on the substrate using a cutter knife, and then, a cellophane tape was attached. Next, when the cellophane tape was peeled off, the number of squares remaining without peeling off the polymerizable liquid crystal film on the lower layer cured film by the retardation material on the substrate was counted. The evaluation results were summarized and shown in the initial column of Table 2 in the form of (the number of cells remaining without peeling)/100. In the case where 90 or more cells remained without the film being peeled off, that is, 90/100 to 100/100, the adhesion was judged to be good.

[Evaluation of durable adhesion]

The retardation material was put in an oven set at a temperature of 80°C and a humidity of 90% on the TAC film by the same method as the above-described evaluation of adhesion, and allowed to stand for 24 hours or more. Then, the phase difference material was taken out, and adhesiveness was evaluated by the method similar to the evaluation of adhesiveness mentioned above. The evaluation results were summarized in Table 2 as adhesion durability.

[Evaluation of orientation sensitivity (Examples 1 to 5)]

Each cured film forming composition of Examples 1 to 5 and Comparative Examples 1 and 2 was rotated on an alkali glass using a spin coater at 2000 rpm for 30 seconds, and then at a temperature of 110° C. for 120 seconds, and a thermal cycle type Heat-drying was performed in an oven to form a cured film. Each of these cured films was irradiated with 313 nm linearly polarized light vertically to form an alignment material. On the alignment material on the substrate, the polymerizable liquid crystal solution RMS03-013C for horizontal alignment manufactured by Merck Ltd. was applied using a spin coater, and then prebaked on a hot plate at 60°C for 60 seconds to have a film thickness of 1.0 μm. A coating film of was formed. The coating film on this substrate was exposed at 1000 mJ/cm ² to prepare a retardation material. The retardation material on the prepared substrate was sandwiched between a pair of polarizing plates, and the state of development of the retardation characteristic in the retardation material was observed, and the exposure amount of polarized UV light required for the alignment material to exhibit liquid crystal orientation was taken as the orientation sensitivity. The evaluation results are put together in Table 2 and shown later. Examples 1 to 5 and Comparative Examples 1 and orientation is formed by using the respective curable film-forming composition of the second material, all the necessary amount of exposure of the polarized UV to indicate the liquid crystal aligning low to 20mJ / cm ² to 40mJ / cm ² Value, and showed good orientation sensitivity.

[Evaluation of orientation sensitivity (Examples 6 and 7)]

Each cured film-forming composition of Examples 6 and 7 was applied on a TAC film using a bar coater, and then heat-dried at a temperature of 110° C. for 120 seconds in a heat-circulating oven to form a cured film. Each of these cured films was irradiated with 313 nm linearly polarized light vertically to form an alignment material. On the alignment material on the substrate, the polymerizable liquid crystal solution for horizontal alignment was applied using a bar coater, and then prebaked on a hot plate at 70° C. for 60 seconds to form a coating film having a thickness of 1.0 μm. The coating film on this substrate was exposed at 300 mJ/cm ² to prepare a retardation material. The retardation material on the prepared substrate was sandwiched between a pair of polarizing plates, and the state of development of the retardation characteristic in the retardation material was observed, and the exposure amount of polarized UV light required for the alignment material to exhibit liquid crystal orientation was taken as the orientation sensitivity. The evaluation results are put together in Table 2 and shown later.

[Evaluation of pattern formation]

Each cured film-forming composition of Examples and Comparative Examples was applied on a TAC film using a bar coater, and then heated and dried at a temperature of 110° C. for 120 seconds in a heat-circulating oven to form a cured film. Linearly polarized light of 313 nm was irradiated to the cured film at 40 mJ/cm ² through a 350 μm line and space mask. Next, after separating the mask and rotating the substrate by 90 degrees, 313 nm linearly polarized light was irradiated vertically by 20 mJ/cm ² to obtain an alignment material in which two kinds of liquid crystal alignment regions having different orientation control directions of liquid crystals were formed by 90 degrees. Got it. On the alignment material on this substrate, a polymerizable liquid crystal solution RMS03-013C for horizontal alignment manufactured by Merck Ltd. was applied using a spin coater, and then prebaked on a hot plate at 60°C for 60 seconds to have a film thickness of 1.0. A coating film of μm was formed. The coating film on this substrate was exposed at 1000 mJ/cm ² , and a patterned retardation material in which two types of regions having different retardation characteristics were regularly arranged was prepared. The patterned retardation material on the fabricated substrate was observed using a polarizing microscope, and the retardation pattern formed without any orientation defects was evaluated as ○, and the orientation defect was evaluated as x. The evaluation results are put together in Table 2 and shown later.

[Evaluation of light transmittance (transparency)]

Each cured film-forming composition of Examples and Comparative Examples was coated on a quartz substrate with rotation at 2000 rpm for 30 seconds using a spin coater, and then heat-dried and baked on a hot plate at a temperature of 110°C for 120 seconds to form a cured film having a thickness of 300 nm. I did. The film thickness was measured using F20 manufactured by Filmetrics, Inc. The transmittance of this cured film with respect to light having a wavelength of 400 nm was measured using an ultraviolet visible spectroscopy photometer (Shimaadzu UV-2550 model number manufactured by Shimadzu Corporation).

[Evaluation results]

The results of performing the above evaluation are shown in Table 2 as described above.

[Table 2]

The cured films obtained by using the cured film forming compositions of Examples 1 to 5 maintained high adhesion even when subjected to high temperature and high humidity treatment, and exhibited excellent adhesion durability.

On the other hand, the cured film obtained by using the cured film forming composition of Comparative Example 1 and Comparative Example 2 was difficult to maintain initial adhesion after high temperature and high humidity treatment.

The alignment material obtained by using the cured film-forming composition of Examples 1 to 5, as in the alignment material obtained by using the cured film-forming composition of Comparative Examples 1 and 2, was all 20 mJ of polarized UV exposure required to exhibit liquid crystal orientation. It was a low value of /cm ² to 40 mJ/cm ² , and showed good orientation sensitivity.

In addition, the alignment material obtained by using the cured film-forming composition of Examples 6 and 7 was compared to the alignment material obtained by using the cured film-forming composition of Comparative Examples 1 and 2, the exposure amount of polarized UV required to show liquid crystal orientation. All of these values were as low as 10 mJ/cm ² , and showed good orientation sensitivity.

The alignment material obtained by using the cured film-forming composition of Examples 1 to 7 exhibited good pattern formation property, similar to the alignment material obtained by using the cured film-forming composition of Comparative Examples 1 and 2.

The cured film obtained by using the cured film forming composition of Examples 1 to 7 was 100% or close to light having a wavelength of 400 nm, similar to the cured film obtained by using the cured film forming composition of Comparative Examples 1 and 2 It showed transmittance and showed good light transmission characteristics.

Industrial availability

The cured film obtained from the cured film forming composition according to the present invention is very useful as a liquid crystal alignment film of a liquid crystal display device or an alignment material for forming an optically anisotropic film provided inside or outside of a liquid crystal display device. It is suitable as a material for forming a patterned retardation material. Furthermore, materials for forming cured films such as protective films, planarization films, and insulating films in various displays such as thin-film transistor (TFT) type liquid crystal display devices and organic EL devices, especially interlayer insulating films of TFT type liquid crystal devices, and protective films of color filters. Alternatively, it is also suitable as a material for forming an insulating film or the like of an organic EL device.

Claims (7)

(A) a compound having a photo-alignment group and one selected from the group consisting of a hydroxy group, a carboxyl group, an amino group and an alkoxysilyl group,
(B) a polymer having at least one of a hydroxy group and a carboxyl group, and
(C) Compounds having a hydroxyl group and a (meth)acrylic group other than the component (A)
A cured film-forming composition comprising a.
The method of claim 1,
The composition for forming a cured film, wherein the compound of the component (A) is a compound having a photo-alignment group and a hydroxyl group.
The method according to claim 1 or 2,
The compound of the component (C) has at least one hydroxy group and one (meth)acrylic group.
The method according to any one of claims 1 to 3,
(D) The cured film-forming composition characterized by further containing a crosslinking agent.
The method according to any one of claims 1 to 4,
(E) The cured film-forming composition characterized by further containing a crosslinking catalyst.
An orientation material obtained by using the cured film-forming composition according to any one of claims 1 to 5.
A retardation material comprising a cured film obtained from the cured film forming composition according to any one of claims 1 to 5.