KR102333902B1 - Composition for forming cured film, alignment material, and retardation material - Google Patents

Abstract

로 표시되는 기로 이루어진 군으로부터 선택되는 하나를 갖는 저분자 화합물 그리고 광배향성기와, 하이드록시기, 카르복실기, 아미드기, 아미노기 및 알콕시실릴기 및 하기 식(2)로 표시되는 기로 이루어진 군으로부터 선택되는 치환기를 갖는 폴리머로부터 선택되는 적어도 1종, (B) 하이드록시기, 카르복실기, 아미노기, 알콕시실릴기 및 상기 식(2)로 표시되는 기로부터 선택되는 적어도 하나의 치환기를 갖는 폴리머, (C) 가교제, 그리고, (D) 1분자 중에 C=C이중결합을 포함하는 중합성기를 적어도 1개를 갖고 또한 N-알콕시메틸기를 적어도 1개 갖는 저분자 화합물을 함유한다. 이 경화막 형성 조성물을 이용하여, 경화막을 형성하고, 광배향기술을 이용하여 배향재를 형성한다. 배향재 상에 중합성 액정을 도포하고, 경화시켜 위상차재를 얻는다.[Problem] To provide a cured film forming composition suitable for forming a cured film having excellent liquid crystal orientation and adhesion durability, to provide an alignment material, and to provide a retardation material using the alignment material.
[Solution means] A cured film forming composition is (A) a photo-alignment group, a hydroxyl group, a carboxyl group, an amino group, an alkoxysilyl group, and the following formula (2)
[Formula 1]

A low molecular weight compound having one selected from the group consisting of a group represented by At least one selected from polymers having, (B) a polymer having at least one substituent selected from a hydroxyl group, a carboxyl group, an amino group, an alkoxysilyl group, and a group represented by the formula (2), (C) a crosslinking agent, and and (D) a low molecular weight compound having at least one polymerizable group containing a C=C double bond in one molecule and at least one N-alkoxymethyl group. A cured film is formed using this cured film formation composition, and an orientation material is formed using the photo-alignment technique. A polymeric liquid crystal is apply|coated on an orientation material, it is made to harden|cure, and retardation material is obtained.

Description

Cured film formation composition, orientation material, and retardation material

TECHNICAL FIELD This invention relates to a cured film formation composition, an orientation material, and retardation material.

In recent years, in the field of display such as a television using a liquid crystal panel, development of a 3D display capable of enjoying a 3D image is being developed as an attempt aimed at improving the performance. In the 3D display, for example, an image with a three-dimensional effect can be displayed by making the viewer's right eye visually recognize the image for the right eye, and making the viewer's left eye visually visually recognize the image for the left eye.

There are various types of 3D display methods for displaying a 3D image, and as methods that do not require special glasses, a lenticular lens method and a Parallax Barrier method are known.

And as one of the display methods in which an observer wears glasses and observes a 3D image, the circular polarization glasses system etc. are known (refer patent document 1, for example.).

In the case of a circularly polarized glasses type 3D display, a phase difference material is usually disposed on a display element that forms an image, such as a liquid crystal panel. In this phase difference material, two types of phase difference areas from which phase difference characteristics differ are respectively arrange|positioned regularly and plural, respectively, and comprises the patterned phase difference material. In addition, hereafter, in this specification, the phase difference material patterned so that the some phase difference area|region from which such phase difference characteristic differs may be arrange|positioned is called a patterned phase difference material.

A patterned retardation material can be produced by optically patterning the retardation material which consists of a polymeric liquid crystal as disclosed by patent document 2, for example. Optical patterning of the retardation material made of polymerizable liquid crystal uses a photo-alignment technique known as the formation of an alignment material for a liquid crystal panel. That is, a coating film made of a material of optical orientation is provided on a substrate, and two types of polarized light having different polarization directions are irradiated thereon. Then, a photo-alignment film is obtained as an alignment material in which two types of liquid-crystal alignment regions having different orientation control directions of 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. Thereafter, the aligned polymerizable liquid crystal is cured to form a patterned retardation material.

In the formation of an alignment material using the optical alignment technology of a liquid crystal panel, an acrylic resin or polyimide resin having a photodimerization site such as a cinnamoyl group and a chalcone group in a side chain is known as a usable optical alignment material. It is reported that these resins exhibit the performance (henceforth also referred to as liquid-crystal orientation) which controls the orientation of a liquid crystal by irradiating polarized light UV (refer patent document 3 - patent document 5.).

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

As mentioned above, the patterning retardation material laminates|stacks the layer of the hardened|cured polymeric liquid crystal on the photo-alignment film which is an orientation material, and is comprised. And the patterned retardation material which has such a laminated structure can be used for the structure of a 3D display as it is the laminated|stacked state.

3D displays are sometimes used for home televisions, and high reliability, particularly long-term durability, is required. Thereby, durability is calculated|required also about the structural member of a 3D display. Therefore, also in a patterning phase difference material, long-term durability becomes essential performance with the thing by which optical patterning is made|formed with high precision, the thing with high light-transmitting characteristic, etc.

However, in the conventional patterning retardation material, it had the subject in the adhesiveness between a photo-alignment film and the layer of a polymeric liquid crystal. For example, between the layers of the photo-alignment film and the polymerizable liquid crystal, peeling tends to occur from the initial stage of formation, and although adhesiveness is excellent at the initial stage of formation, the adhesiveness decreases with the passage of time, and peeling tends to occur.

Among these, peeling between the layers of the photo-alignment film and the polymerizable liquid crystal, which occurs with the passage of time, becomes a defect in the actually used 3D display, and causes a decrease in the display quality of the 3D display. Accordingly, there is a demand for a patterned retardation material capable of high-precision optical patterning, excellent in light transmission characteristics, and furthermore, excellent in durability. In particular, the patterning retardation 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 this specification) for maintaining the excellent adhesion for a long period of time redemption is requested.

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

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

An object of the present invention is to provide a retardation material capable of high-precision optical patterning and excellent in durability.

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

A first aspect of the present invention is

(A) a low molecular weight compound having at least one substituent selected from the group consisting of a photo-alignment group, a hydroxyl group, a carboxyl group, an amide group, an amino group, an alkoxysilyl group, and a group represented by the following formula (2) And a photo-alignment group, a hydride At least one selected from a polymer having at least one substituent selected from the group consisting of a hydroxy group, a carboxyl group, an amide group, an amino group, an alkoxysilyl group, and a group represented by the following formula (2);

[Formula 1]

(In the formula, R ⁶² represents an alkyl group, an alkoxy group, or a phenyl group.)

(B) a polymer having at least one substituent selected from the group consisting of a hydroxyl group, a carboxyl group, an amide group, an amino group, an alkoxysilyl group, and a group represented by the formula (2);

(C) a crosslinking agent, and

(D) a low molecular weight compound having at least one polymerizable group containing a C=C double bond in one molecule and at least one N-alkoxymethyl group

It relates to the cured film formation composition characterized by containing.

In the first aspect of the present invention, component (A) is preferably one selected from a low molecular weight compound having a photo-alignment group, a hydroxyl group and/or a carboxyl group, and a polymer having a photo-alignment group, a hydroxyl group and/or a carboxyl group. do.

1st aspect of this invention WHEREIN: It is preferable that the compound of (D)component is a compound which has a structure represented by following formula (1).

[Formula 2]

(Wherein, R ¹ represents a hydrogen atom or a methyl group, and R ² represents a hydrogen atom or a straight-chain or branched-chain alkyl group having 1 to 10 carbon atoms.),

1st aspect of this invention WHEREIN: It is preferable that the compound of (D)component is a compound which has a structure represented by a following formula (X2).

[Formula 3]

[Wherein, R ⁵¹ represents a hydrogen atom or a methyl group. R ⁵³ is each independently a linear or branched alkylene group having 2 to 20 carbon atoms, a divalent group consisting of an aliphatic ring having 5 to 6 carbon atoms, or a divalent aliphatic group including an aliphatic ring having 5 to 6 carbon atoms and may contain an ether bond in the structure of these groups. R ⁵⁴ is a divalent to 9 valent group having a structure in which an additional 1 to 8 hydrogen atoms are removed from a linear or branched alkyl group having 2 to 20 carbon atoms, or a hydrogen atom from an alicyclic group having 5 to 6 carbon atoms A divalent to 9-valent group having a structure in which 1 to 8 are removed, or a divalent to 9-valent aliphatic group including an aliphatic ring having 5 to 6 carbon atoms is represented, and an ether bond may be included in the structure. R ⁵² represents a linear or branched chain alkyl group having 1 to 20 carbon atoms, a monovalent group consisting of an aliphatic ring having 5 to 6 carbon atoms, or a monovalent aliphatic group including an aliphatic ring having 5 to 6 carbon atoms, and these groups One methylene group or a plurality of non-adjacent methylene groups may be substituted with an ether bond. Z is >NCOO- or -OCON< (where "-" represents one bond. In addition, ">" and "<" represent two bonds. One bond of N atoms is -CH ₂ OR ⁵² is bonded.). r is a natural number between 2 and 9.]

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

A 2nd aspect of this invention is obtained using the cured film formation composition of a 1st aspect of this invention, It relates to the orientation material characterized by the above-mentioned.

A 3rd aspect of this invention has a cured film obtained from the cured film formation composition of the 1st aspect of this invention, It relates to the retardation material characterized by the above-mentioned.

ADVANTAGE OF THE INVENTION According to the 1st aspect of this invention, it has the outstanding liquid-crystal orientation and light transmittance, and can provide the cured film formation composition suitable for formation of the cured film excellent in close_contact|adherence durability.

According to the 2nd aspect of this invention, it is excellent in liquid-crystal orientation and light transmittance, and can provide the orientation material excellent in adhesion durability.

According to the 3rd aspect of this invention, highly accurate optical patterning is possible, and the 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 a cured polymerizable liquid crystal is required. And the cured film formation composition suitable for formation of the orientation material of such performance is calculated|required.

MEANS TO SOLVE THE PROBLEM As a result of this inventor earnestly examining in order to meet the request mentioned above, the cured film obtained from the cured film formation composition which has a specific composition is excellent in light transmittance, and liquid-crystal orientation which regulates liquid-crystal orientation by polarization exposure and found that it can be used as an orientation material. Furthermore, this inventor discovered that the cured film obtained from the cured film formation composition which has the specific composition showed the outstanding adhesion durability between the layers of the polymeric liquid crystal polymerization-hardened thereon. That is, the cured film obtained from the cured film formation composition which has a specific composition of this invention can comprise the photo-alignment film excellent in the close_contact|adherence durability between the layers of a polymerizable liquid crystal.

Below, the cured film formation composition of this invention is demonstrated in detail, giving specific examples, such as a component. And the cured film and orientation material of this invention using the cured film formation composition of this invention, and the retardation material and liquid crystal display element etc. which are formed using the orientation material are demonstrated.

<Cured film forming composition>

The cured film formation composition of this embodiment of this invention is at least selected from the group which consists of (A) a photo-alignment group, a hydroxyl group, a carboxyl group, an amide group, an amino group, an alkoxysilyl group, and the group represented by said Formula (2) A low molecular weight compound having one substituent and a photo-alignment group, a hydroxyl group, a carboxyl group, an amide group, an amino group, an alkoxysilyl group, and a polymer having at least one substituent selected from the group consisting of the group represented by Formula (2) (B) a polymer having at least one substituent selected from a hydroxyl group, a carboxyl group, an amide group, an amino group, an alkoxysilyl group, and a group represented by the formula (2), (C) a crosslinking agent as a component, And (D) It is a thermosetting cured film formation composition containing the low molecular compound which has at least 1 polymerizable group containing a C=C double bond in 1 molecule, and has at least 1 N-alkoxymethyl group. Furthermore, in addition to (A) component, (B)component, (C)component, and (D)component, a crosslinking catalyst can be contained as (E)component. Furthermore, other additives may be contained as long as the effects of the present invention are not impaired. It may also contain a solvent.

Hereinafter, the detail of each component is demonstrated.

[(A) component]

(A) component of the cured film formation composition of this embodiment is at least 1 sort(s) chosen from a low molecular photo-alignment component and a high molecular weight photo-alignment component. First, the case where (A) component is a low molecular photo-alignment component is demonstrated below. (A) The low molecular weight photo-alignment component which is a component is a component which provides photo-alignment property to the cured film of this embodiment obtained from the cured film formation composition of this embodiment, Comparing with the polymer of the below-mentioned (B) component used as a base, a low molecular weight is a photo-alignment component of

In the cured film formation composition of this embodiment, the low molecular weight photo-alignment component which is (A) component is a photo-alignment group, and a hydroxyl group, a carboxyl group, an amide group, an amino group, an alkoxysilyl group, and the said Formula (2) It can be set as a low molecular weight compound having at least one substituent selected from the group consisting of:

In addition, in this invention, the photo-alignment group means the functional group of the structural site|part to photodimerize or photoisomerize.

(A) The structural site to photodimerize which the low molecular weight compound of the component can have as a photo-alignment group is a site|part which forms a dimer by light irradiation, As the specific example, a cinnamoyl group, a chalcone group, a coumarin group , an anthracene group, and the like. Among these, a cinnamoyl group is preferable from high transparency in a visible region and high photodimerization reactivity.

Incidentally, the structural moiety to be photoisomerized that the low molecular weight compound of component (A) can have as a photo-alignment group refers to a structural moiety that changes to a cis form and a trans form by light irradiation, and specific examples thereof include azobenzene structure and stilbene structure. and the like. Among these, the azobenzene structure is preferable at the point of high reactivity.

Furthermore, as an alkoxysilyl group in this embodiment, a trimethoxysilyl group, a triethoxysilyl group, a triisopropoxysilyl group, a dimethoxymethylsilyl group, a diethoxymethylsilyl group, a diisopropoxymethylsilyl group , a methoxydimethylsilyl group, an ethoxydimethylsilyl group, and the like.

A low molecular weight compound having any one of a photo-alignment group, a hydroxyl group, a carboxyl group, an amide group, an amino group, an alkoxysilyl group, and a substituent selected from the group represented by the formula (2) is, for example, a compound represented by the following formula am.

[Formula 4]

In the above formula, A ¹ and A ² each independently represent a hydrogen atom or a methyl group, and X ¹¹ represents a single bond, an ether bond, an ester bond, an amide bond, a urea bond, a urethane bond, an amino bond, a carbonyl or a group thereof. A structure formed by bonding 1 to 3 substituents selected from an alkyl group having 1 to 18 carbon atoms, a phenyl group, a biphenyl group, or a combination thereof through one or two or more bonds selected from combinations. 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. In this case, the alkyl group, phenyl group, biphenyl group and cyclohexyl group having 1 to 18 carbon atoms may be bonded via a covalent bond, an ether bond, an ester bond, an amide bond, a urethane bond, a carbonyl or a urea bond.

In the above formula, 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. X ¹⁴ each independently represents a single bond, an alkylene group having 1 to 20 carbon atoms, a divalent aromatic ring group, or a divalent aliphatic ring group. Here, the alkylene group having 1 to 20 carbon atoms may be branched or straight chain. X ¹⁵ represents a hydroxyl group, a carboxyl group, an amino group, an alkoxysilyl group, or a group represented by the formula (2). However, when X ¹⁴ is a single bond, X ¹⁵ is a hydroxyl group or an amino group. X ⁰ represents a single bond, an oxygen atom or a sulfur atom. However, when X ¹⁴ is a ^{single bond, X 0 is} also a single bond.

In addition, when a benzene ring is included in these substituents, 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. Alternatively, 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, or alkoxy having 1 to 4 carbon atoms. group, a halogen atom, a trifluoromethyl group or a cyano group.

In addition, as the alkyl group having 1 to 18 carbon atoms as defined above, for example, a methyl group, an ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group group, n-pentyl group, 1-methyl-n-butyl group, 2-methyl-n-butyl group, 3-methyl-n-butyl group, 1,1-dimethyl-n-propyl group, 1,2-dimethyl -n-propyl group, 2,2-dimethyl-n-propyl group, 1-ethyl-n-propyl group, n-hexyl group, 1-methyl-n-pentyl group, 2-methyl-n-pentyl group, 3 -Methyl-n-pentyl group, 4-methyl-n-pentyl group, 1,1-dimethyl-n-butyl group, 1,2-dimethyl-n-butyl group, 1,3-dimethyl-n-butyl group, 2,2-dimethyl-n-butyl group, 2,3-dimethyl-n-butyl group, 3,3-dimethyl-n-butyl group, 1-ethyl-n-butyl group, 2-ethyl-n-butyl group , 1,1,2-trimethyl-n-propyl group, 1,2,2-trimethyl-n-propyl group, 1-ethyl-1-methyl-n-propyl group, 1-ethyl-2-methyl-n- Propyl group, n-heptyl group, 1-methyl-n-hexyl group, 2-methyl-n-hexyl group, 3-methyl-n-hexyl group, 1,1-dimethyl-n-pentyl group, 1,2- Dimethyl-n-pentyl group, 1,3-dimethyl-n-pentyl group, 2,2-dimethyl-n-pentyl group, 2,3-dimethyl-n-pentyl group, 3,3-dimethyl-n-pentyl group , 1-ethyl-n-pentyl group, 2-ethyl-n-pentyl group, 3-ethyl-n-pentyl group, 1-methyl-1-ethyl-n-butyl group, 1-methyl-2-ethyl-n -Butyl group, 1-ethyl-2-methyl-n-butyl group, 2-methyl-2-ethyl-n-butyl group, 2-ethyl-3-methyl-n-butyl group, n-octyl group, 1- Methyl-n-heptyl group, 2-methyl-n-heptyl group, 3-methyl-n-heptyl group, 1,1-dimethyl-n-hexyl group, 1,2-dimethyl-n-hexyl group, 1,3 -dimethyl-n-hexyl group, 2,2-dimethyl-n-hexyl group, 2,3-dimethyl-n-hexyl group, 3,3-dimethyl-n-hexyl group, 1-ethyl-n-hexyl group, 2-ethyl-n-hexyl group, 3-ethyl-n-hexyl group, 1-methyl-1-ethyl-n-pentyl group, 1-methyl-2-ethyl-n-pentyl group, 1-methyl-3- Ethyl-n-pentyl group, 2-methyl-2-ethyl-n-pentyl group, 2-methyl-3-ethyl-n-pentyl group, 3-methyl-3-ethyl-n-pentyl group, n-nonyl group , n-decyl group, n-undecyl group, n-dodecyl group group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group and n-octadecyl group. Similarly, examples of the alkyl group having 1 to 4 carbon atoms include groups having the corresponding number of carbon atoms among the groups mentioned above.

Further, as the alkoxy group having 1 to 10 carbon atoms, the alkoxy group having 1 to 4 carbon atoms, and the alkylthio group having 1 to 10 carbon atoms, the group having the corresponding number of carbon atoms among the above-mentioned alkyl groups oxidized or thiolated can be heard

Further, examples of the alkylene group having 1 to 20 carbon atoms include a divalent group obtained by removing one hydrogen atom from the alkyl group having 19 to 20 carbon atoms, such as the aforementioned alkyl group and n-nonadecyl group and n-eicosyl group.

In the formula (2), ^{examples of the alkyl group for R 62} include an alkyl group having 1 to 10 carbon atoms, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, etc. Among the alkyl groups, the group having the corresponding number of carbon atoms is mentioned. Examples of the alkoxy group for R ⁶² include an alkoxy group having 1 to 10 carbon atoms, for example, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, etc. Among the converted groups, a group having a corresponding number of carbon atoms can be mentioned.

As a group represented by said Formula (2), the following structures etc. are mentioned, for example.

[Formula 5]

(A) As a specific example of the low molecular weight compound which has a photo-alignment group and a hydroxyl group which is a component, For example, 4-(8-hydroxyoctyloxy) cinnamic acid methyl ester, 4-(6-hydroxyhexyloxy) Cinnamon methyl ester, 4-(4-hydroxybutyloxy) cinnamic acid methyl ester, 4-(3-hydroxypropyloxy) cinnamic acid methyl ester, 4-(2-hydroxyethyloxy) cinnamic acid methyl ester, 4-hydroxy Methyloxycinnamic acid methyl ester, 4-hydroxycinnamic acid methyl ester, 4-(8-hydroxyoctyloxy)cinnamic acid ethyl ester, 4-(6-hydroxyhexyloxy)cinnamic acid ethyl ester, 4-(4-hydroxyl) Butyloxy) 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-hydroxycinnamic 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-hydroxyoctyl) Oxy) cinnamic acid biphenyl ester, 4-(6-hydroxyhexyloxy) cinnamic acid biphenyl ester, 4-(4-hydroxybutyloxy) cinnamic acid biphenyl ester, 4- (3-hydroxypropyloxy) cinnamic acid biphenyl ester Phenyl ester, 4-(2-hydroxyethyloxy) cinnamic acid biphenyl ester, 4-hydroxymethyloxy cinnamic acid biphenyl ester, 4-hydroxy cinnamic acid biphenyl ester, cinnamic acid 8-hydroxyoctyl ester, cinnamic acid 6-hyde Hydroxyhexyl ester, cinnamic acid 4-hydroxybutyl ester, cinnamic acid 3-hydroxypropyl ester, cinnamic acid 2-hydroxyethyl ester, cinnamic acid hydroxymethyl ester, 4-(8-hydroxyoctyloxy) chalcone, 4-(6 -Hydroxyhexyloxy) chalcone, 4- (4-hydroxybutyloxy) chalcone, 4- (3-hydroxypropyloxy) chalcone, 4- (2-hydroxyethyloxy) chalcone, 4-hydroxymethyl Oxychalcone, 4-hydroxychalcone, 4'-(8-hydroxyoctyloxy)chalcone, 4'-(6-hydroxy Hexyloxy) chalcone, 4'-(4-hydroxybutyloxy) chalcone, 4'-(3-hydroxypropyloxy) chalcone, 4'-(2-hydroxyethyloxy) chalcone, 4'-hydroxyl Methyloxychalcone, 4'-hydroxychalcone, 7-(8-hydroxyoctyloxy)coumarin, 7-(6-hydroxyhexyloxy)coumarin, 7-(4-hydroxybutyloxy)coumarin, 7- (3-hydroxypropyloxy) coumarin, 7-(2-hydroxyethyloxy) coumarin, 7-hydroxymethyloxycoumarin, 7-hydroxycoumarin, 6-hydroxyoctyloxycoumarin, 6-hydroxyhexyloxy Coumarin, 6-(4-hydroxybutyloxy)coumarin, 6-(3-hydroxypropyloxy)coumarin, 6-(2-hydroxyethyloxy)coumarin, 6-hydroxymethyloxycoumarin, 6-hydroxyl Coumarin, 4-[4-(8-hydroxyoctyloxy)benzoyl]cinnamic acid methyl ester, 4-[4-(6-hydroxyhexyloxy)benzoyl]cinnamic acid methyl ester, 4-[4-(4-hydroxyl) Roxybutyloxy)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] cinnamic acid ethyl ester, 4- [4- (6-hydroxyhexyloxy)benzoyl]cinnamic acid ethyl ester, 4-[4-(4-hydroxybutyloxy)benzoyl]cinnamic acid ethyl ester, 4-[4-(3-hydroxypropyloxy)benzoyl]cinnamic acid Ethyl ester, 4-[4-(2-hydroxyethyloxy)benzoyl]cinnamic acid ethyl ester, 4-[4-hydroxymethyloxybenzoyl]cinnamic acid ethyl ester, 4-[4-hydroxybenzoyl]cinnamic acid ethyl ester; 4-[4-(8-hydroxyoctyloxy)benzoyl]cinnamic acid tertbutyl ester, 4-[4-(6-hydroxyhexyloxy)benzoyl]cinnamic acid tertiary butyl ester, 4-[4-(4 -Hydroxybutyloxy)benzoyl]cinnamic acid tertbutyl ester, 4-[4-(3-hydroxypropyloxy)benzoyl]cinnamic acid tertiary butyl ester, 4-[4-(2-hydroxyethyloxy)benzoyl] Tertiary butyl ester of cinnamon, 4- [4-hydroxymethyloxybenzoyl] tertbutyl ester of cinnamon, 4-[4-(8-hydroxyoctyloxy)benzoyl]cinnamic acid phenyl ester, 4-[4-(6-hydroxyhexyloxy)benzoyl]cinnamic acid phenyl ester, 4-[4-(4-hydroxybutyl) Oxy)benzoyl]cinnamic acid phenyl ester, 4-[4-(3-hydroxypropyloxy)benzoyl]cinnamic acid phenyl ester, 4-[4-(2-hydroxyethyloxy)benzoyl]cinnamic acid phenylester, 4-[4 -Hydroxymethyloxybenzoyl]cinnamic acid phenyl ester, 4-[4-hydroxybenzoyl]cinnamic acid phenyl ester, 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] Cinnamon 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 low molecular weight compound which has a photo-alignment group and a carboxyl group as a component, Cinnamon acid, ferulic acid, 4-nitro cinnamic acid, 4-methoxycinnamic acid, 3,4-dimethoxycinnamic acid, coumarin-3-car Main acid, 4-(N,N-dimethylamino)cinnamic acid, 4-(6-methacryloxyhexyl-1-oxy)cinnamic acid, 4-(6-acryloxyhexyl-1-oxy)cinnamic acid, 4-(3- Methacryloxypropyl-1-oxy)cinnamic acid, 4-(4-(3-methacryloxypropyl-1-oxy)acryloxy)benzoic acid, 4-(4-(6-methacryloxyhexyl-1-oxy) Benzoyloxy) cinnamic acid etc. are mentioned.

Specific examples of the low molecular weight compound having a photo-alignment group and an amide group as component (A) include cinnamic acid amide, 4-methyl cinnamic acid amide, 4-ethyl cinnamic acid amide, 4-methoxy cinnamic acid amide, 4-ethoxy cinnamic acid amide 4 -(6-methacryloxyhexyl-1-oxy)cinnamamide, 4-(6-methacryloxyhexyl-1-oxy)-N-(4-cyanophenyl)cinnamamide, 4-(6-methacryl) Oxyhexyl-1-oxy) -N-bishydroxyethyl cinnamamide etc. are mentioned.

(A) As a specific example of the low molecular weight compound which has a photo-alignment group and an amino group as component, 4-amino cinnamic acid methyl ester, 4-amino cinnamic acid ethyl ester, 3-amino cinnamic acid methyl ester, 3-amino cinnamic acid ethyl ester, etc. can be heard

(A) As a specific example of the low molecular weight compound which has a photo-alignment group and an alkoxysilyl group as component, 4-(3-trimethoxysilylpropyloxy)cinnamic acid methyl ester, 4-(3-triethoxysilylpropyloxy)cinnamic acid Methyl ester, 4-(3-trimethoxysilylpropyloxy)cinnamic acid ethyl ester, 4-(3-triethoxysilylpropyloxy)cinnamic acid ethyl 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.

(A) As a specific example of the low molecular weight compound which has the photo-alignment group which is a component, and group represented by said Formula (2), the compound etc. which are represented by the following formula are mentioned (In formula, Me represents a methyl group.).

[Formula 6]

As (A) component, the low molecular weight compound which the polymeric group couple|bonded with the group which the photo-alignment site|part and the thermally-reactive site|part further couple|bonded with the following formula (1a) via a spacer is preferable.

[Formula 7]

(wherein, R ¹⁰¹ is a hydroxyl group, an amino group, a hydroxyphenoxy group, a carboxylphenoxy group, an aminophenoxy group, an aminocarbonylphenoxy group, a phenylamino group, a hydroxyphenylamino group, a carboxylphenylamino group, an aminophenylamino group, represents a hydroxyalkylamino group or a bis(hydroxyalkyl)amino group, X ¹⁰¹ represents a phenylene group which may be optionally substituted with an arbitrary substituent, and the benzene ring in the definition of these substituents may be substituted with a substituent.)

Examples of the substituent in the case where the benzene ring may be substituted with a substituent include an alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group and an isobutyl group; Haloalkyl groups, such as a trifluoromethyl group; Alkoxy groups, such as a methoxy group and an ethoxy group; halogen atoms such as iodine, bromine, chlorine and fluorine; cyano group; A nitro group etc. are mentioned.

In said R ¹⁰¹ , a hydroxyl group and an amino group are preferable, and a hydroxyl group is especially preferable.

The spacer is a divalent group selected from linear alkylene, branched chain alkylene, cyclic alkylene and phenylene, or a group formed by bonding two or more divalent groups. In this case, the bond between the divalent groups constituting the spacer, the bond between the spacer and the group represented by the formula (1a), and the bond between the spacer and the polymerizable group include a single bond, an ester bond, an amide bond, a urea bond, and a urethane. bonds, carbonyl or ether bonds. When there are a plurality of the divalent groups, the divalent groups may be the same or different, and when the bonds are plural, the bonds may be the same or different.

Specific examples of the monomer in which the polymerizable group is bonded to the group to which the photo-alignment moiety and the heat-reactive moiety are bonded as component (A) include 4-(6-methacryloxyhexyl-1-oxy)cinnamic acid, 4-(6-acryloxy) Hexyl-1-oxy)cinnamic acid, 4-(3-methacryloxypropyl-1-oxy)cinnamic acid, 4-(4-(3-methacryloxypropyl-1-oxy)acryloxy)benzoic acid, 4-(4 -(6-methacryloxyhexyl-1-oxy)benzoyloxy)cinnamic acid, 4-(6-methacryloxyhexyl-1-oxy)cinnamamide, 4-(6-methacryloxyhexyl-1-oxy)- N-(4-cyanophenyl)cinnamamide, 4-(6-methacryloxyhexyl-1-oxy)-N-bishydroxyethyl cinnamamide, etc. are mentioned.

(A) Although the above specific example is given as for the low molecular-weight photo-alignment component which is a component, it is not limited to these.

Next, the detail in case (A) component is a polymer, ie, a high molecular weight polymer, is demonstrated below.

When component (A) contained in the cured film forming composition of the present invention is a high molecular weight polymer, component (A) is a polymer having a photo-alignment group, that is, a functional group of a structural site to be photodimerized or photoisomerized as a photo-alignment group. It is preferable that it is a polymer having, in particular, an acrylic copolymer having at least a photodimerization site. In addition, in addition to the photodimerization site, at least one substituent selected from the group consisting of a hydroxyl group, a carboxyl group, an amide group, an amino group, an alkoxysilyl group, and a group represented by the formula (2) (hereinafter, heat including these groups It is preferable that it is an acrylic copolymer which has a crosslinking site|part).

In the present invention, the acrylic copolymer refers to a copolymer obtained by polymerizing a monomer having an unsaturated double bond, such as acrylic acid ester, methacrylic acid ester, or styrene.

(A) The acrylic copolymer having a photodimerization moiety and a thermal crosslinking moiety (hereinafter also referred to as a specific copolymer) of component (A) may be an acrylic copolymer having such a structure, and the main chain skeleton of the polymer constituting the acrylic copolymer And it is not specifically limited with respect to the kind etc. of a side chain.

As a photodimerization site|part, a cinnamoyl group, a chalcone group, a coumarin group, anthracene group, etc. are mentioned. Among these, a cinnamoyl group is preferable from the high transparency in a visible region, and the high photodimerization reactivity. As a more preferable cinnamoyl group and a substituent containing a cinnamoyl structure, the structure represented by following formula [1] or Formula [2] is mentioned. In addition, in this specification, the group in which the benzene ring in a cinnamoyl group is a naphthalene ring is also included in "cinnamoyl group" and "a substituent containing a cinnamoyl structure."

[Formula 8]

In the formula [1], X ¹ represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, a phenyl group or a biphenyl group. In this case, the phenyl group and the biphenyl group may be substituted by any one of a halogen atom and a cyano group.

In the formula [2], X ² represents a hydrogen atom, a cyano group, an alkyl group having 1 to 18 carbon atoms, a phenyl group, a biphenyl group, or a cyclohexyl group. In this case, an alkyl group having 1 to 18 carbon atoms, a phenyl group, a biphenyl group, and a cyclohexyl group are selected from a covalent bond, an ether bond, an ester bond, an amide bond, a urea bond, a urethane bond, an amino bond, a carbonyl group, or a combination thereof. Multiple types may be bonded through one type or two or more types of bonding.

In Formulas [1] and [2], A represents any one of Formula [A1], Formula [A2], Formula [A3], Formula [A4], Formula [A5], and Formula [A6].

In the formulas [A1], [A2], [A3], [A4], [A5], and [A6], R ³¹ , R ³² , R ³³ , R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ and R ³⁸ each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, a trifluoromethyl group or a cyano group.

A thermal crosslinking site|part is a site|part couple|bonded with (B) component by heating, The specific example of the hydroxyl group, a carboxyl group, an amide group, an amino group, an alkoxysilyl group, the group represented by Formula (2), etc. are mentioned have.

(A) It is preferable that the acrylic copolymer of component has a weight average molecular weight of 3,000-200,000. If the weight average molecular weight exceeds 200,000 and is excessive, solubility in a solvent may decrease and handleability may decrease. Resistance may fall or heat resistance may fall.

As for the synthesis method of the acrylic copolymer which has a photodimerization site|part and a thermal crosslinking site|part of (A) component, the method of copolymerizing the monomer which has a photodimerization site|part and the monomer which has a thermal crosslinking site|part is simple.

As a monomer which has a photodimerization site|part, the monomer which has a cinnamoyl group, a chalcone group, a coumarin group, anthracene group, etc. is mentioned, for example. Among these, a monomer having a cinnamoyl group is particularly preferable from the viewpoint of high transparency in the visible region and high photodimerization reactivity.

Among them, a monomer having a substituent containing a cinnamoyl group and a cinnamoyl structure having a structure represented by Formula [1] or Formula [2] is more preferable. A specific example of such a monomer is a monomer represented by the following formula [3] or [4].

[Formula 9]

In the formula [3], X ¹ represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, a phenyl group or a biphenyl group. In this case, the phenyl group and the biphenyl group may be substituted by any one of a halogen atom and a cyano group.

L ¹ and L ² each independently represent a covalent bond, an ether bond, an ester bond, an amide bond, a urea bond, or a urethane bond.

In the formula [4], X ² represents a hydrogen atom, a cyano group, an alkyl group having 1 to 18 carbon atoms, a phenyl group, a biphenyl group, or a cyclohexyl group. In this case, the alkyl group, phenyl group, biphenyl group, and cyclohexyl group having 1 to 18 carbon atoms may be bonded via a covalent bond, an ether bond, an ester bond, an amide bond, or a urea bond.

In the formulas [3] and [4], X ³ and X ⁵ each independently represent a single bond, an alkylene group having 1 to 20 carbon atoms, a divalent aromatic ring group, or a divalent aliphatic ring group. Here, the alkylene group having 1 to 20 carbon atoms may be branched or straight chain.

In the formula [3] and the formula [4], X ⁴ and X ⁶ represents a polymerizable group. Specific examples of the polymerizable group include an acryloyl group, a methacryloyl group, a styrene group, a maleimide group, an acrylamide group, and a methacrylamide group.

In Formulas [3] and [4], A is similar to Formula [1] and Formula [2], Formula [A1], Formula [A2], Formula [A3], Formula [A4], Formula [A5] and any one of formula [A6].

Moreover, as a C1-C18 alkyl group and a C1-C20 alkylene group in the definition of the group in said formula [1]-[4], the example of said alkyl group and an alkylene group is mentioned.

Examples of the monomer having a thermal crosslinking moiety include 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, and 4-hydroxy Oxybutyl acrylate, 4-hydroxybutyl methacrylate, 2,3-dihydroxypropyl acrylate, 2,3-dihydroxypropyl methacrylate, diethylene glycol monoacrylate, diethylene glycol monomethacrylic Late, caprolactone 2- (acryloyloxy) ethyl ester, caprolactone 2- (methacryloyloxy) ethyl ester, poly (ethylene glycol) ethyl ether acrylate, poly (ethylene glycol) ethyl ether methacrylate, 5-acryloyloxy-6-hydroxynorbornene-2-carboxylic-6-lactone, 5-methacryloyloxy-6-hydroxynorbornene-2-carboxylic-6-lactone, etc. a monomer having a hydroxyl group; Acrylic acid, methacrylic acid, crotonic acid, mono-(2-(acryloyloxy)ethyl)phthalate, mono-(2-(methacryloyloxy)ethyl)phthalate, N-(carboxyphenyl)maleimide, N Monomers having a carboxyl group, such as -(carboxyphenyl)methacrylamide and N-(carboxyphenyl)acrylamide; Phenolic hydroxyls such as hydroxystyrene, N-(hydroxyphenyl)methacrylamide, N-(hydroxyphenyl)acrylamide, N-(hydroxyphenyl)maleimide, and N-(hydroxyphenyl)maleimide a monomer having a group; monomers having an amide group such as acrylamide and methacrylamide; a monomer having an alkoxysilyl group such as methacryloyloxypropyltrimethoxysilane, methacryloyloxypropyltriethoxysilane, acryloyloxypropyltrimethoxysilane, and acryloyloxypropyltriethoxysilane; monomers having an amino group, such as dimethylaminoethyl methacrylate, diethylaminomethacrylate, and tert-butylaminoethyl methacrylate; The monomer etc. which have group represented by Formula (2), such as 2-acetoacetoxy ethyl acrylate and 2-acetoacetoxy ethyl methacrylate, are mentioned.

The amount of the monomer having a photodimerization moiety and a monomer having a thermal crosslinking moiety used to obtain a specific copolymer is based on the total amount of all monomers used to obtain a specific copolymer, the monomer having a photodimerization moiety is 40 It is preferable that mass % - 95 mass %, and the monomer which has a thermal crosslinking site|part is 5 mass % - 60 mass %. By setting the monomer content having a photodimerization moiety to 40% by mass or more, it is possible to provide high sensitivity and good liquid crystal orientation. On the other hand, by setting it as 95 mass % or less, sufficient thermosetting can be provided and it is highly sensitive and favorable liquid-crystal orientation can be maintained.

In addition, in the cured film forming composition of the present invention, when obtaining a specific copolymer, a monomer copolymerizable with a monomer having a photodimerization site and a thermal crosslinking site (hereinafter also referred to as a specific functional group) (hereinafter referred to as a non-reactive functional group) Also referred to as a monomer) may be used in combination.

As a specific example of such a monomer, an acrylic acid ester compound, a methacrylic acid ester compound, a maleimide compound, an acrylamide compound, acrylonitrile, maleic anhydride, a styrene compound, a vinyl compound, etc. are mentioned.

Hereinafter, although the specific example of the said monomer is given, this invention is not limited to these.

As the above-mentioned acrylic acid ester compound, for example, methyl acrylate, ethyl acrylate, isopropyl acrylate, benzyl acrylate, naphthyl acrylate, anthryl acrylate, anthryl methyl acrylate, phenyl acrylate, Glycidyl acrylate, 2,2,2-trifluoroethyl acrylate, tert-butyl acrylate, cyclohexyl acrylate, isobornyl acrylate, 2-methoxyethyl acrylate, methoxytriethylene glycol acrylate , 2-ethoxyethyl acrylate, tetrahydrofurfuryl acrylate, 3-methoxybutyl acrylate, 2-methyl-2-adamantyl acrylate, 2-propyl-2-adamantyl acrylate, 8- Methyl-8-tricyclodecyl acrylate, 8-ethyl-8- tricyclodecyl acrylate, etc. are mentioned.

As the above-mentioned methacrylic acid ester compound, for example, methyl methacrylate, ethyl methacrylate, isopropyl methacrylate, benzyl methacrylate, naphthyl methacrylate, anthryl methacrylate, anthryl Methyl methacrylate, phenyl methacrylate, glycidyl methacrylate, 2,2,2-trifluoroethyl methacrylate, tert-butyl methacrylate, cyclohexyl methacrylate, isobornyl methacrylate, 2-Methoxyethyl methacrylate, methoxytriethylene glycol methacrylate, 2-ethoxyethyl methacrylate, tetrahydrofurfuryl methacrylate, 3-methoxybutyl methacrylate, 2-methyl-2- Adamantyl methacrylate, γ-butyrolactone methacrylate, 2-propyl-2-adamantyl methacrylate, 8-methyl-8-tricyclodecyl methacrylate, and 8-ethyl-8- Tricyclodecyl methacrylate etc. are mentioned.

Examples of the vinyl compound described above include methyl vinyl ether, benzyl vinyl ether, vinyl naphthalene, vinyl carbazole, allyl glycidyl ether, 3-ethenyl-7-oxabicyclo [4.1.0] heptane; 1,2-epoxy-5-hexene and 1,7-octadiene monoepoxide; and the like.

As a styrene compound mentioned above, styrene, methylstyrene, chlorostyrene, and bromostyrene etc. are mentioned, for example.

As a maleimide compound mentioned above, maleimide, N-methyl maleimide, N-phenyl maleimide, N-cyclohexyl maleimide, etc. are mentioned, for example.

Although the method of obtaining the specific copolymer used for the cured film formation composition of this invention is not specifically limited, For example, The monomer which has a specific functional group (a monomer which has a photodimerization site|part and a monomer which has a thermal crosslinking site|part), as needed It is obtained by polymerization reaction at a temperature of 50°C to 110°C in a solvent in which a monomer having a non-reactive functional group, a polymerization initiator, and the like are coexisted. At this time, the solvent to be used is not particularly limited as long as it dissolves a monomer having a specific functional group, a monomer having a non-reactive functional group used as necessary, a polymerization initiator, and the like. As a specific example, the solvent described in the solvent mentioned later is mentioned.

The specific copolymer obtained in this way is the state of the solution melt|dissolved in the solvent normally, and can use it as it is as a solution of (A) component in this invention.

In addition, the solution of the specific copolymer obtained as described above is put under stirring with diethyl ether or water to re-precipitate, and the resulting precipitate is filtered and washed, and then dried under normal pressure or reduced pressure, at room temperature or heat, It can be set as the powder of a specific copolymer. By this operation, the polymerization initiator and unreacted monomer coexisting with the specific copolymer can be removed, and as a result, a refined powder of the specific copolymer is obtained. What is necessary is just to melt|dissolve the obtained powder again in a solvent, and to perform said operation repeatedly, when it cannot fully refine|purify by one operation.

In the cured film formation composition of this invention, as (A) component, the powder of the said specific copolymer may be used as it is, or the powder may be re-dissolved in the solvent mentioned later, for example, and you may use it in the state of a solution.

In addition, in this embodiment, the mixture of several types of specific copolymers may be sufficient as the acrylic copolymer of (A) component.

As mentioned above, in this invention, as (A) component, a low molecular weight compound or a high molecular weight specific copolymer can be used. In addition, (A) component may be the mixture of 1 or more types of low molecular-weight compounds, and a specific high molecular weight copolymer, respectively.

[(B) component]

The component (B) contained in the cured film formation composition of this embodiment is at least one substituent selected from a hydroxyl group, a carboxyl group, an amide group, an amino group, an alkoxysilyl group, and the group represented by the said Formula (2) , which is also called a specific functional group). (B) As an alkoxysilyl group in a component, a trimethoxysilyl group, a triethoxysilyl group, a triisopropoxysilyl group, a dimethoxymethylsilyl group, a diethoxymethylsilyl group, a diisopropoxymethylsilyl group , a methoxydimethylsilyl group, an ethoxydimethylsilyl group, and the like.

(B) Examples of the component polymer include 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 novolac resins, melamine formaldehyde resins, etc. polymers having a linear or branched structure, cyclic polymers such as cyclodextrins, etc. can be heard

(B) As a specific polymer which is a component, Preferably, an acrylic polymer, hydroxyalkyl cyclodextrins, cellulose, polyether polyol, polyester polyol, polycarbonate polyol, and polycaprolactone polyol are mentioned.

As an acrylic polymer which is a preferable example of the specific polymer of component (B), it is a polymer obtained by superposing|polymerizing the monomer which has unsaturated double bonds, such as acrylic acid, methacrylic acid, styrene, a vinyl compound, The monomer containing the monomer which has a specific functional group. Or it may be a polymer obtained by polymerizing the mixture, and there is no particular limitation on the backbone of the main chain of the polymer constituting the acrylic polymer, the kind of side chains, and the like.

As a monomer having a specific functional group, a monomer having a polyethylene glycol ester group, a monomer having a hydroxyalkyl ester group having 2 to 5 carbon atoms, a monomer having a phenolic hydroxy group, a monomer having a carboxyl group, a monomer having an amide group, an amino group The monomer which has a group represented by a monomer, an alkoxysilyl group, and said Formula (2) is mentioned.

A monomer having the above-mentioned polyethylene glycol, there may be mentioned a monoacrylate or monomethacrylate of _{H- (OCH 2 CH 2) n} -OH. The value of n is 2 to 50, preferably 2 to 10.

As a monomer which has a C2-C5 hydroxyalkyl ester group mentioned above, 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 the above-mentioned phenolic hydroxyl group, p-hydroxystyrene, m-hydroxystyrene, and o-hydroxystyrene are mentioned, for example.

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

As a monomer which has the above-mentioned amino group in a side chain, 2-aminoethyl acrylate, 2-aminoethyl methacrylate, aminopropyl acrylate, and aminopropyl methacrylate are mentioned, for example.

As a monomer which has the above-mentioned alkoxysilyl group in a side chain, 3-acryloxypropyl trimethoxysilane, 3-acryloxy propyl triethoxysilane, 3-methacryloxy propyl trimethoxysilane, 3- and methacryloxypropyltrimethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, allyltrimethoxysilane, and allyltriethoxysilane.

As a monomer which has the group represented by the said Formula (2) mentioned above in a side chain, 2-acetoacetoxyethyl acrylate, 2-acetoacetoxyethyl methacrylate, etc. are mentioned, for example.

Moreover, in this embodiment, in synthesizing the acrylic polymer which is an example of (B) component, unless the effect of this invention is impaired, a hydroxyl group, a carboxyl group, an amide group, an amino group, an alkoxysilyl group, and said Formula (2) ) may be used in combination with a monomer having none of the groups represented by .

As a specific example of such a monomer, an acrylic acid ester compound, a methacrylic acid ester compound, a maleimide compound, an acrylonitrile, maleic anhydride, a styrene compound, a vinyl compound, etc. are mentioned.

Examples of the acrylic acid ester compound include methyl acrylate, ethyl acrylate, isopropyl acrylate, benzyl acrylate, naphthyl acrylate, anthryl acrylate, anthryl methyl acrylate, phenyl acrylate, 2,2 ,2-trifluoroethyl acrylate, tert-butyl acrylate, cyclohexyl acrylate, isobornyl acrylate, 2-methoxyethyl acrylate, methoxytriethylene glycol acrylate, 2-ethoxyethyl acrylate, Tetrahydrofurfuryl acrylate, 3-methoxybutyl acrylate, 2-methyl-2-adamantyl acrylate, 2-propyl-2-adamantyl acrylate, 8-methyl-8-tricyclodecyl acrylate , and 8-ethyl-8-tricyclodecyl acrylate.

As a methacrylic acid ester compound, For example, methyl methacrylate, ethyl methacrylate, isopropyl methacrylate, benzyl methacrylate, naphthyl methacrylate, anthryl methacrylate, anthryl methyl methacrylate Rate, phenyl methacrylate, 2,2,2-trifluoroethyl methacrylate, tert-butyl methacrylate, cyclohexyl methacrylate, isobornyl methacrylate, 2-methoxyethyl methacrylate, methacrylate Toxytriethylene glycol methacrylate, 2-ethoxyethyl methacrylate, tetrahydrofurfuryl methacrylate, 3-methoxybutyl methacrylate, 2-methyl-2-adamantyl methacrylate, 2-propyl -2-adamantyl methacrylate, 8-methyl-8-tricyclodecyl methacrylate, and 8-ethyl-8-tricyclodecyl methacrylate, etc. are mentioned.

As a maleimide compound, maleimide, N-methyl maleimide, N-phenyl maleimide, N-cyclohexyl maleimide, etc. are mentioned, for example.

As a styrene compound, styrene, methyl styrene, chloro styrene, bromostyrene etc. are mentioned, for example.

Examples of the vinyl compound include vinyl ether, methyl vinyl ether, benzyl vinyl ether, 2-hydroxyethyl vinyl ether, phenyl vinyl ether, and propyl vinyl ether.

It is preferable that the usage-amount of the monomer which has a specific functional group used to obtain the acrylic polymer which is an example of (B) component is 2 mol% - 98 mol% based on the total amount of all the monomers used in order to obtain the acrylic polymer which is (B) component. do. When there is too little the monomer which has a specific functional group, the liquid-crystal orientation of the cured film obtained becomes inadequate easily, and when excessive, compatibility with (A) component falls easily.

(B) The method of obtaining the acrylic polymer which is an example of a component is not specifically limited, For example, For example, the monomer containing the monomer which has a specific functional group, the monomer which does not have a specific functional group, and the solvent which coexisted a polymerization initiator etc. as needed. It is obtained by polymerization at a temperature of 50°C to 110°C. At this time, the solvent used will not be specifically limited if it dissolves the monomer which has a specific functional group, the monomer which does not have a specific functional group used as needed, a polymerization initiator, etc. As a specific example, it describes in the term of the [solvent] mentioned later.

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

In addition, the solution of the acrylic polymer as an example of component (B) obtained by the above method is added to diethyl ether or water under stirring for reprecipitation, and the resulting precipitate is filtered and washed, then dried at room temperature under normal pressure or reduced pressure, or It can be heat-dried and it can be set as the powder of the acrylic polymer which is an example of (B) component. By the above-mentioned operation, the polymerization initiator and unreacted monomer which coexist with the acrylic polymer which is an example of (B) component can be removed, As a result, the powder of the acrylic polymer which is an example of the refined (B) component is obtained. What is necessary is just to make the obtained powder re-dissolve in a solvent again, and just to perform the above-mentioned operation repeatedly, when it cannot fully refine|purify by one operation.

(B) It is preferable that weight average molecular weights are 3000-20000, as for the acrylic polymer which is a preferable example of a component, it is more preferable that it is 4000-150000, It is still more preferable that it is 5000-100000. If the weight average molecular weight exceeds 200000 and is excessive, the solubility in solvents may decrease and handleability may decrease. Heat resistance may fall. In addition, the weight average molecular weight is a value obtained using polystyrene as standard data by gel permeation chromatography (GPC). Hereinafter, it is assumed that it is the same also in this specification.

Next, as polyether polyol which is a preferable example of the specific polymer of (B) component, propylene oxide, polyethyleneglycol, polypropylene in polyhydric alcohol, such as polyethyleneglycol, polypropylene glycol, propylene glycol, bisphenol A, triethylene glycol, sorbitol, What added glycol etc. is mentioned. Specific examples of polyether polyols include ADEKA Adeka polyether P series, G series, EDP series, BPX series, FC series, CM series, NOF Corporation UNIOX (Juniox) (registered trademark) HC-40, HC- 60, ST-30E, ST-40E, G-450, G-750, UNIOL (ユニオ-l) (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 preferable example of the specific polymer of component, ethylene glycol, propylene glycol, butylene glycol, polyethylene glycol, polypropylene glycol, What made diol react is mentioned. Specific examples of the polyester polyol include POLYLITE (registered trademark) manufactured by DIC, 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.

(B) As a polycaprolactone polyol which is a preferable example of the specific polymer of component, what carried out ring-opening polymerization of epsilon caprolactone using polyalcohols, such as trimethylol propane and ethylene glycol, as an initiator is mentioned. Specific examples of polycaprolactone polyol include POLYLITE (registered trademark) OD-X-2155, OD-X-640, OD-X-2568 manufactured by DIC, PLACCEL (registered trademark) 205, L205AL, 205U manufactured by Daicel Corporation. , 208, 210, 212, L212AL, 220, 230, 240, 303, 305, 308, 312, 320, and the like.

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

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

(B) As a cyclodextrin which is a preferable example of the specific polymer of component, Cyclodextrins, such as alpha-cyclodextrin, beta-cyclodextrin, and gamma cyclodextrin, methyl-alpha-cyclodextrin, methyl- beta-cyclodextrin, and methyl- Methylated cyclodextrin such as γ-cyclodextrin, 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, Hydroxyalkyl cyclodextrins, such as 2, 3- dihydroxypropyl-(beta)-cyclodextrin and 2, 3- dihydroxypropyl-(gamma)-cyclodextrin, etc. are mentioned.

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

[Formula 10]

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. Examples of the alkyl group having 1 to 4 carbon atoms include a group having the corresponding number of carbon atoms among the alkyl groups exemplified above or below.

As for the melamine formaldehyde resin of (B) component, it is preferable that the methylol group produced|generated at the time of polycondensation of melamine and formaldehyde from a viewpoint of storage stability is alkylated.

The method for obtaining the melamine formaldehyde resin of component (B) is not particularly limited, but generally, melamine and formaldehyde are mixed, and then made weakly alkaline using sodium carbonate or ammonia, etc., and then synthesized by heating at 60 ° C. to 100 ° C. do. Furthermore, a methylol group can be alkoxylated by making it react with alcohol.

(B) It is preferable that weight average molecular weights are 250-5000, As for the melamine formaldehyde resin of a component, it is more preferable that it is 300-4000, It is still more preferable that it is 350-3500. If the weight average molecular weight exceeds 5000 and is excessive, solubility in solvents may decrease and handling properties may decrease. The effect of improving the heat resistance may not be sufficiently exhibited.

In embodiment of this invention, you may use the melamine formaldehyde resin of (B) component in a liquid form, or the solution form which melt|dissolved the refined liquid again in the solvent mentioned later.

Moreover, in embodiment of this invention, the mixture of the melamine formaldehyde resin of multiple types (B) component may be sufficient as the melamine formaldehyde resin of (B) component.

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

Cured film formation composition of this embodiment WHEREIN: The polymer of (B) component can also be used in the form of a powder or the form of a solution which melt|dissolved the refined powder again in the solvent mentioned later.

Moreover, the cured film formation composition of this embodiment WHEREIN: (B) component may be a mixture of multiple types of polymers illustrated as (B) component.

[(C)component]

The cured film formation composition of this embodiment contains a crosslinking agent as (C)component. In more detail, (C)component reacts with (A)component mentioned above, (B)component, and (D)component mentioned later, and when (A)component is a low molecular-weight photo-alignment component, ( A) It is a crosslinking agent that reacts at a lower temperature than the sublimation temperature of the component. (C) component (A) at a lower temperature than the sublimation temperature of component, (A) the low molecular weight compound and / or polymer of a hydroxy group, a carboxyl group, an amide group, an amino group, an alkoxysilyl group and the formula (2) A substituent selected from the group represented, a substituent selected from a hydroxyl group, a carboxyl group, an amide group, an amino group, an alkoxysilyl group, and a group represented by the formula (2) contained in the component (B), the compound of the component (D) combine with As a result, when (A) component, (B) component, and (D)component, and the crosslinking agent which is (C)component thermally react so that it may mention later, it can suppress that (A) component sublimates. And the cured film formation composition of this embodiment can form the orientation material with high photoreaction efficiency as a cured film.

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

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

Specific examples of the alkoxymethylated glycoluril include, 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 a commercial item, compounds, such as a glycoluril compound manufactured by Mitsui Cytec Ltd (trade name: CYMEL (registered trademark) 1170, POWDERLINK (power-link) (registered trademark) 1174)), methylated urea resin (trade name: UFR (registered trademark) ) 65), butylated urea resin (trade name: UFR (registered trademark) 300, U-VAN10S60, U-VAN10R, U-VAN11HV), urea/formaldehyde resin (high condensation type, manufactured by Dainippon Ink and Chemicals, Inc.) A brand name: BECKAMINE (ベCKAMINE) (trademark) J-300S, BECKAMINE P-955, BECKAMINE N) etc. are mentioned.

As a specific example of alkoxymethylation benzoguanamine, tetramethoxymethylbenzoguanamine etc. are mentioned, for example. As a commercially available product, Mitsui Cytec Ltd. (trade name: CYMEL (registered trademark) 1123), Sanwa Chemical Co., Ltd. (trade name: NIKALAC (registered trademark) BX-4000, NIKALAC BX-37, NIKALAC BL-60, NIKALAC BX-55H), etc. are mentioned.

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

In addition, 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 the 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 can be mentioned. Commercially available products of the melamine compound include: CYMEL (registered trademark) 303 (manufactured by Mitsui Cytec Ltd.) Ltd.) etc. are mentioned.

Moreover, as (C)component, hydroxymethyl groups, such as N-hydroxymethyl acrylamide, N-methoxymethyl methacrylamide, N-ethoxymethyl acrylamide, N-butoxymethyl methacrylamide, or an alkoxymethyl group A polymer prepared using an acrylamide compound substituted with or a methacrylamide compound may also be used.

Examples of such polymers 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-butoxymethyl acrylamide, benzyl methacrylate and 2-hydroxypropyl methacrylate, etc. are mentioned. The weight average molecular weight of such a polymer is 1000-50000, Preferably it is 2000-20000, More preferably, it is 3000-150000, More preferably, it is 3000-50000.

These crosslinking agents can be used individually or in combination of 2 or more types.

Content of the crosslinking agent of (C)component in the cured film formation composition of this embodiment is 100 mass parts of the total amount of the polymer of at least 1 sort(s) chosen from the low molecular compound which is (A) component, and a polymer, and (B)component Based on this, it is preferable that it is 10 mass parts - 100 mass parts, More preferably, they are 15 mass parts - 80 mass parts. When content of a crosslinking agent is too little, the solvent tolerance and heat resistance of the cured film obtained from a cured film formation composition fall, and the orientation sensitivity at the time of photo-alignment falls. On the other hand, when the content is excessive, the optical orientation and storage stability may decrease.

[(D)component]

Component (D) contained in the cured film formation composition of this embodiment is a low molecular weight compound which has at least 1 polymerizable group containing a C=C double bond in 1 molecule, and has at least 1 N-alkoxymethyl group.

(D) When using the cured film formed from the cured film formation composition of this embodiment containing a component as an orientation material, so that the adhesiveness of an orientation material and the layer of a polymeric liquid crystal may improve, the polymerizable functional group of a polymeric liquid crystal and an orientation material The crosslinking sites may be linked by a covalent bond. As a result, the retardation material of this embodiment formed by laminating a cured polymerizable liquid crystal on the alignment material of this embodiment can maintain strong adhesiveness even under high-temperature and high-quality conditions, and can exhibit high durability against peeling etc. .

Examples of the polymerizable group containing a C=C double bond include an acryl group, a methacryl group, a vinyl group, an allyl group, and a maleimide group.

N of the N-alkoxymethyl group, that is, the nitrogen atom, is a nitrogen atom of amide, a nitrogen atom of thioamide, a nitrogen atom of urea, a nitrogen atom of thiourea, a nitrogen atom of urethane, and a nitrogen atom of a nitrogen-containing heterocyclic ring. A nitrogen atom etc. are mentioned. Accordingly, the N-alkoxymethyl group includes a nitrogen atom of amide, a nitrogen atom of thioamide, a nitrogen atom of urea, a nitrogen atom of thiourea, a nitrogen atom of urethane, a nitrogen atom bonded to an adjacent position of a nitrogen atom of a nitrogen-containing heterocyclic ring, etc. and a structure in which an alkoxymethyl group is bonded to a nitrogen atom selected from

(D) As a component, although what is necessary is just to have said group, Preferably, the compound represented by following formula (1) is mentioned, for example.

[Formula 11]

(Wherein, R ¹ represents a hydrogen atom or a methyl group, and R ² represents a hydrogen atom or a linear or branched alkyl group having 1 to 10 carbon atoms)

Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, 1-methyl- n-butyl group, 2-methyl-n-butyl group, 3-methyl-n-butyl group, 1,1-dimethyl-n-propyl group, 1,2-dimethyl-n-propyl group, 2,2-dimethyl -n-propyl group, 1-ethyl-n-propyl group, n-hexyl group, 1-methyl-n-pentyl group, 2-methyl-n-pentyl group, 3-methyl-n-pentyl group, 4-methyl -n-pentyl group, 1,1-dimethyl-n-butyl group, 1,2-dimethyl-n-butyl group, 1,3-dimethyl-n-butyl group, 2,2-dimethyl-n-butyl group, 2,3-dimethyl-n-butyl group, 3,3-dimethyl-n-butyl group, 1-ethyl-n-butyl group, 2-ethyl-n-butyl group, 1,1,2-trimethyl-n- Propyl group, 1,2,2-trimethyl-n-propyl group, 1-ethyl-1-methyl-n-propyl group, 1-ethyl-2-methyl-n-propyl group, n-heptyl group, 1-methyl -n-hexyl group, 2-methyl-n-hexyl group, 3-methyl-n-hexyl group, 1,1-dimethyl-n-pentyl group, 1,2-dimethyl-n-pentyl group, 1,3- Dimethyl-n-pentyl group, 2,2-dimethyl-n-pentyl group, 2,3-dimethyl-n-pentyl group, 3,3-dimethyl-n-pentyl group, 1-ethyl-n-pentyl group, 2 -Ethyl-n-pentyl group, 3-ethyl-n-pentyl group, 1-methyl-1-ethyl-n-butyl group, 1-methyl-2-ethyl-n-butyl group, 1-ethyl-2-methyl -n-Butyl group, 2-methyl-2-ethyl-n-butyl group, 2-ethyl-3-methyl-n-butyl group, n-octyl group, 1-methyl-n-heptyl group, 2-methyl- n-heptyl group, 3-methyl-n-heptyl group, 1,1-dimethyl-n-hexyl group, 1,2-dimethyl-n-hexyl group, 1,3-dimethyl-n-hexyl group, 2,2 -Dimethyl-n-hexyl group, 2,3-dimethyl-n-hexyl group, 3,3-dimethyl-n-hexyl group, 1-ethyl-n-hexyl group, 2-ethyl-n-hexyl group, 3- Ethyl-n-hexyl group, 1-methyl-1-ethyl-n-pentyl group, 1-methyl-2-ethyl-n-pentyl group, 1-methyl-3-ethyl-n-pentyl group, 2-methyl- 2-ethyl-n-pentyl group, 2-methyl-3-ethyl-n-pentyl group, 3-methyl-3-ethyl-n-pentyl group, n-nonyl group, n-decyl group, etc. are mentioned.

Specific examples of the compound represented by the formula (1) include N-butoxymethylacrylamide, N-isobutoxymethylacrylamide, N-methoxymethylacrylamide, N-methoxymethylmethacrylamide, N- Methylolacrylamide etc. are mentioned.

(D) As another aspect of the compound which has a polymeric group containing C=C double bond of component and N-alkoxymethyl group, Preferably, the compound represented by a following formula (X2) is mentioned, for example .

[Formula 12]

[Wherein, R ⁵¹ represents a hydrogen atom or a methyl group. R ⁵³ represents a linear or branched alkylene group having 2 to 20 atoms, a divalent group consisting of an aliphatic ring having 5 to 6 carbon atoms, or a divalent aliphatic group including an aliphatic ring having 5 to 6 carbon atoms, the structure It may contain an ether linkage. R ⁵⁴ is a divalent to 9 valent group having a structure in which 1 to 8 hydrogen atoms have been removed from a linear or branched alkyl group having 2 to 20 carbon atoms, or an aliphatic ring group having 5 to 6 carbon atoms, an additional hydrogen atom from 1 to It represents a divalent to 9-valent group having a structure in which 8 elements have been removed, or a divalent to 9-valent aliphatic group containing an aliphatic ring having 5 to 6 carbon atoms, and may contain an ether bond in the structure. R ⁵² represents a linear or branched chain alkyl group having 1 to 20 carbon atoms, a monovalent group consisting of an aliphatic ring having 5 to 6 carbon atoms, or a monovalent aliphatic group including an aliphatic ring having 5 to 6 carbon atoms, and these groups One methylene group or a plurality of non-adjacent methylene groups may be substituted with an ether bond. Z is >NCOO- or -OCON< (where "-" represents one bond. In addition, ">" and "<" represent two bonds. Any one of the N atoms is -CH ₂ OR ⁵² is bonded.). r is a natural number between 2 and 9.]

Bivalent to consisting of a structure in which 1 to 8 hydrogen atoms are removed from an alkylene group having 2 to 20 carbon atoms in the definition of R ^{53 and a linear or branched alkyl group having 2 to 20 carbon atoms in the definition of R 54} Specific examples of the 9-valent group include a divalent to 9-valent group obtained by removing 1 to 8 hydrogen atoms from the alkyl group having 2 to 20 carbon atoms shown below.

Specific examples of the alkyl group having 2 to 20 carbon atoms include an ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group, n-pentyl group , 1-methyl-n-butyl group, 2-methyl-n-butyl group, 3-methyl-n-butyl group, 1,1-dimethyl-n-propyl group, n-hexyl group, 1-methyl-n- pentyl group, 2-methyl-n-pentyl group, 1,1-dimethyl-n-butyl group, 1-ethyl-n-butyl group, 1,1,2-trimethyl-n-propyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n -heptadecyl group, n-octadecyl group, n-nonadecyl group, and n-eicosyl group are mentioned, In addition, a group bonded by one or more of these groups within the range of up to 20 carbon atoms, and one of these groups is methylene Alternatively, a group in which a plurality of non-adjacent methylene groups are substituted with ether bonds can be exemplified.

Among these, an alkylene group having 2 to 10 carbon atoms is preferable, R ⁵³ is an ethylene group, and R ⁵⁴ is a hexylene group, from the viewpoint of availability of raw materials and the like.

Specific examples of the alkyl group having 1 to 20 carbon atoms in the definition of R ⁵² include specific examples of the alkyl group having 2 to 20 carbon atoms in the description of the definitions of ^{R 53} and R ^{54 and a methyl group.} Among these, a C1-C6 alkyl group is preferable, and a methyl group, an ethyl group, n-propyl group or n-butyl group is especially preferable.

Examples of the aliphatic ring group having 5 to 6 carbon atoms in the definitions of R ⁵² , R ⁵³ and R ^{54 include a cyclopentyl group and a group based on a cyclohexyl group.} A divalent to 9 valent group having a structure in which an additional 1 to 8 hydrogen atoms are removed from these aliphatic cyclic groups having 5 to 6 carbon atoms, and monovalent or divalent to including an aliphatic ring having 5 to 6 carbon atoms and a group in which one or more 9-valent aliphatic groups are bonded within the range of up to 20 carbon atoms, and further, a group in which one methylene or a plurality of non-adjacent methylene groups is substituted with an ether bond can be mentioned. .

Although 2 or more and 9 or less natural number are mentioned as r, 2-6 are especially preferable.

Compound (X2) is obtained by a manufacturing method shown by the following reaction scheme. That is, a carbamate compound having an acryl or methacryl group represented by the following formula (X2-1) (hereinafter also referred to as compound (X2-1)) is reacted in a solvent containing trimethylsilyl chloride and paraformaldehyde to obtain the following It is prepared by synthesizing the intermediate represented by the formula (X2-2), adding an alcohol represented by ^{R 52 -OH to the reaction solution, and reacting.}

[Formula 13]

In the formula, R ⁵¹ , R ⁵² , R ⁵³ , R ⁵⁴ , Z and r represent the above meanings, and X represents -NHCOO- or -OCONH-.

The amount of trimethylsilyl chloride and paraformaldehyde to be used for compound (X2-1) is not particularly limited, but in order to complete the reaction, 1.0 to 6.0 equivalent times of trimethylsilyl chloride per carbamate bond in the molecule, para Formaldehyde is preferably used in an amount of 1.0 to 3.0 equivalents, and more preferably, the equivalent of trimethylsilyl chloride is more than that of paraformaldehyde.

The reaction solvent is not particularly limited as long as it is inert to the reaction, and examples thereof include hydrocarbons such as hexane, cyclohexane, benzene and toluene; halogen-based hydrocarbons such as methylene chloride, carbon tetrachloride, chloroform and 1,2-dichloroethane; ethers such as diethyl ether, diisopropyl ether, 1,4-dioxane, and tetrahydrofuran; nitriles such as acetonitrile and propionitrile; nitrogen-containing polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, and 1,3-dimethyl-2-imidazolidinone; and pyridines such as pyridine and picoline. These solvents may be used independently, or 2 or more types of these may be mixed and used for them. Preferably they are methylene chloride and chloroform, More preferably, they are methylene chloride.

The amount of the solvent used (reaction concentration) is not particularly limited, but the reaction may be carried out without using a solvent, or in the case of using a solvent, 0.1 to 100 mass times the solvent may be used with respect to compound (X2-1). have. Preferably it is 1-30 mass times, More preferably, it is 2-20 mass times.

The reaction temperature is not particularly limited, but is, for example, -90 to 200°C, preferably -20 to 100°C, and more preferably -10 to 50°C.

The reaction time is usually 0.05 to 200 hours, preferably 0.5 to 100 hours.

The reaction can be carried out under normal pressure or under pressure, and may be batchwise or continuous.

When making it react, you may add a polymerization inhibitor. As such a polymerization inhibitor, BHT (2,6-di-tert-butyl-para-cresol), hydroquinone, para-methoxyphenol, etc. can be used, and if it inhibits polymerization of acryl group and methacryl group, it is particularly limited it doesn't happen

The amount of addition of the polymerization inhibitor is not particularly limited, but is 0.0001 to 10 wt%, preferably 0.01 to 1 wt%, based on the total amount (mass) of compound (X2-1). In this specification, wt% means mass%.

In the step of reacting the intermediate (X2-2) with alcohol, a base may be added to suppress hydrolysis under acidic conditions. Examples of the base include pyridines such as pyridine and picoline, and tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine and tributylamine. Preferably they are triethylamine and diisopropylethylamine, More preferably, they are triethylamine. The amount of addition in the case of adding the base is not particularly limited, but may be used in an amount of 0.01 to 2.0 equivalents, more preferably 0.5 to 1.0 equivalents, based on the amount of trimethylsilyl chloride used in the reaction.

Further, after obtaining the intermediate (X2-2) from the compound (X2-1), the intermediate (X2-2) may be reacted by adding alcohol without isolating the intermediate (X2-2).

The synthesis method of compound (X2-1) is not particularly limited, but by reacting (meth)acryloyloxyalkylisocyanate and a polyol compound, or by reacting a hydroxyalkyl (meth)acrylate compound with a polyisocyanate compound, can

Specific examples of (meth)acryloyloxyalkyl isocyanate include, for example, 2-methacryloyloxyethyl isocyanate (manufactured by Showa Denko KK, trade name: KARENZ (KARENZ) MOI [registered trademark]), 2-acrylo yloxyethyl isocyanate (manufactured by Showa Denko KK, trade name: KARENZ AOI [registered trademark]) and the like.

Specific examples of the polyol compound include ethylene glycol, propylene glycol, 1,4-butanediol, 1,3-butanediol, 1,5-pentanediol, neopentyl glycol, 3-methyl-1,5-pentanediol, 1, Diol compounds, such as 6-hexanediol and 1, 4- cyclohexane dimethanol, triol compounds, such as glycerol and trimethylol propane, pentaerythritol, dipentaerythritol, diglycerol, etc. are mentioned.

Specific examples of the hydroxyalkyl (meth)acrylate compound include 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 4 -Hydroxybutyl acrylate, 4-hydroxybutyl methacrylate, diethylene glycol monoacrylate, diethylene glycol monomethacrylate, poly (ethylene glycol) ethyl ether acrylate, poly (ethylene glycol) ethyl ether methacrylic The monomer etc. which have hydroxyl groups, such as a rate, are mentioned.

Specific examples of the polyisocyanate compound include aliphatic diisocyanates such as hexamethylene diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate and dimer acid diisocyanate, isophorone diisocyanate, and 4,4'-methylenebis(cyclohexyl). isocyanate), ω,ω'-diisocyanate, alicyclic diisocyanate such as dimethylcyclohexane, lysine ester triisocyanate, 1,6,11-undecane triisocyanate, 1,8-diisocyanate-4-isocyanate methyloctane, 1 and triisocyanates such as 3,6-hexamethylene triisocyanate and bicycloheptane triisocyanate.

These (meth)acryloyloxyalkyl isocyanate compounds, polyol compounds, hydroxyalkyl (meth)acrylate compounds, and polyisocyanate compounds are generally commercially available and can be synthesized by a known method.

Content of (D)component in the cured film formation composition of embodiment of this invention is at least 1 sort(s) chosen from the low molecular compound and polymer which are (A)component, the polymer of (B)component, and the crosslinking agent of (C)component To 100 parts by mass of the total amount of , preferably 0.1 parts by mass to 40 parts by mass, more preferably 5 parts by mass to 35 parts by mass. Adhesiveness sufficient to the cured film formed can be provided by content of (D)component being 0.1 mass part or more. However, when there are more than 40 mass parts, the storage stability of a cured film formation composition may fall.

Moreover, the cured film formation composition of this embodiment WHEREIN: (D)component may be several types of mixtures of the compound of (D)component.

[(E) component]

The cured film formation composition of this embodiment can contain a crosslinking catalyst as (E)component further in addition to (A) component, (B) component, (C)component, and (D)component mentioned above have.

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

When an acid or a thermal acid generator is used as the component (E), the component (E) is a sulfonic acid group-containing compound, 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 sulfonic acids, its hydrate, salt, etc. are mentioned.

In addition, as a compound which generates an acid by heat, for example, bis(tosyloxy)ethane, bis(tosyloxy)propane, bis(tosyloxy)butane, p-nitrobenzyltosylate, o-nitrobenzyltosylate , 1,2,3-phenylentris (methylsulfonate), p-toluenesulfonic acid pyridinium salt, p-toluenesulfonic acid morphonium 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, cyanomethyl p-toluenesulfonate, 2,2,2-trifluoroethyl p-toluenesulfonate, 2-hydroxybutyl p-tosylate, N-ethyl-4-toluenesulfonamide, and compounds represented by the following formulas [TAG-1] to [TAG-41]; and the like. .

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

[Formula 18]

[Formula 19]

[Formula 20]

Content of (E) component in the cured film formation composition of embodiment of this invention is at least 1 sort(s) chosen from the low molecular compound which is (A) component, and a polymer, the polymer of (B) component, and the crosslinking agent of (C)component And with respect to 100 mass parts of the total amount of the low molecular weight compound of (D)component, Preferably it is 0.01 mass part - 10 mass parts, More preferably, it is 0.05 mass part - 8 mass parts, More preferably, it is 0.1 mass part - 6 mass parts is wealth (E) By making content of a component into 0.01 mass part or more, sufficient thermosetting and solvent tolerance can be provided and the high sensitivity with respect to exposure can also be provided. Moreover, the storage stability of a cured film formation composition can be made favorable by setting it as 10 mass parts or less.

[Other Additives]

The cured film formation composition of embodiment of this invention can contain other additives, unless the effect of this invention is impaired.

As another additive, a sensitizer can be contained, for example. When a sensitizer forms the cured film of embodiment of this invention from the cured film formation composition of this embodiment, when promoting the photoreaction, it becomes effective.

As a sensitizer, derivatives, such as benzophenone, anthracene, anthraquinone, and thioxanthone, a nitrophenyl compound, etc. are mentioned. Among them, N,N-diethylaminobenzophenone, which is a derivative of benzophenone, and 2-nitrofluorene, 2-nitrofluorenone, 5-nitroacenaphthene, 4-nitrobiphenyl, and 4-nitrocinnamic acid, which are nitrophenyl compounds, 4 -Nitrostilbene, 4-nitrobenzophenone, 5-nitroindole are especially preferred.

These sensitizers are not specifically limited to what was mentioned above. These can be used individually or in combination of 2 or more types of compounds.

In the embodiment of the present invention, the use ratio of the sensitizer is 0.1 parts by mass to 20 parts by mass with respect to 100 parts by mass of the total amount of the component (A), component (B), component (C), and component (D). It is preferable, More preferably, they are 0.2 mass parts - 10 mass parts. When this ratio is too small, the effect as a sensitizer may not fully be acquired, and when excessive, the transmittance|permeability of the cured film formed may fall or a coating film may become rough.

Moreover, the cured film formation composition of embodiment of this invention is a silane coupling agent, surfactant, a rheology modifier, a pigment, dye, a storage stabilizer, an antifoamer, and antioxidant, as another additive, unless the effect of this invention is impaired. and the like.

[solvent]

The cured film formation composition of embodiment of this invention is used in the solution state melt|dissolved in the solvent in many cases. The solvent used at this time dissolves (A) component, (B) component, (C)component and (D)component, (E) component and/or other additives as needed, such a dissolving ability As long as it is a solvent to have, the type and structure are not particularly limited.

When the specific example of a solvent is given, 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, cyclopentyl methyl ether, isopropyl alcohol, toluene, xylene, methyl ethyl ketone, cyclopentanone, cyclohexanone, 2-butane one, 3-methyl-2-pentanone, 2-pentanone, 2-heptanone, γ-butyrolactone, ethyl 2-hydroxypropionate, 2-hydroxy-2-methylpropionate ethyl, ethyl ethoxyacetate; Ethyl hydroxyacetate, 2-hydroxy-3-methyl butanoate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, methyl 3-ethoxypropionate, 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 individually by 1 type or in combination of 2 or more types. 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 of good film-forming properties and high safety.

<Preparation of a cured film forming composition>

The cured film formation composition of embodiment of this invention is a thermosetting cured film formation composition which has photo-alignment property. As above-mentioned, the cured film formation composition of this embodiment is at least 1 sort(s) chosen from the low molecular weight compound which is (A) component, and a polymer, (B) The hydroxyl group, carboxyl group, amide group, amino group, alkoxysilyl which are (B) component A polymer having at least one substituent selected from a group and a group represented by the formula (2), a crosslinking agent as component (C), and a polymerizable group containing a C=C double bond in one molecule as component (D) contains at least one low molecular weight compound having at least one N-alkoxymethyl group. Moreover, a crosslinking catalyst can be contained as (E)component. And unless the effect of this invention is impaired, other additives can be contained and, further, a solvent can be contained.

(A) As for the compounding ratio of component and (B) component, 5:95-80:20 are preferable in mass ratio. (B) When content of component is excessive, liquid-crystal orientation falls easily, and when too little, solvent tolerance falls, and orientation falls easily.

The preferable example of the cured film formation composition of this embodiment is as follows.

[1]: (A) a low molecular weight compound having at least one substituent selected from the group consisting of a photo-alignment group as component, a hydroxyl group, a carboxyl group, an amide group, an amino group, an alkoxysilyl group, and a group represented by the formula (2) (Low molecular weight photo-alignment component) and (B) component hydroxy group, carboxyl group, amide group, amino group, alkoxysilyl group and a polymer having at least one substituent selected from the group represented by the formula (2) in the mass ratio It is 5:95 to 80:20, and 10 parts by mass to 100 parts by mass (C) based on 100 parts by mass of the total amount of at least one selected from the low molecular weight compound and the polymer as the component (A) and the polymer of the component (B) 0.1 parts by mass to 40 parts by mass with respect to 100 parts by mass of the total amount of the crosslinking agent of the component, and at least one selected from the low molecular weight compound and the polymer of the component (A), the polymer of the component (B), and the crosslinking agent of the component (C) The cured film formation composition containing the low molecular compound which has at least 1 polymerizable group containing a C=C double bond in 1 molecule which is a component (D) by mass, and has at least 1 N-alkoxymethyl group.

[2]: The mixing ratio of the component (A) and the component (B) is 5:95 to 80:20 in mass ratio, and at least one selected from the low molecular weight compound and the polymer as the component (A) and the polymer of the component (B) Based on 100 parts by mass of the total amount, 10 parts by mass to 100 parts by mass of (C) component, and at least one selected from the low molecular weight compound and polymer (A) component, the polymer of the component (B), and the component (C) The cured film formation composition containing 0.1 mass parts - 40 mass parts (D)component and a solvent with respect to 100 mass parts of the total amount of a crosslinking agent.

[3]: The mixing ratio of the component (A) and the component (B) is 5:95 to 80:20 in mass ratio, and at least one selected from the low molecular weight compound and the polymer as the component (A) and the polymer of the component (B) Based on 100 parts by mass of the total amount, 10 parts by mass to 100 parts by mass of (C) component, at least one selected from the low molecular weight compound and polymer (A) component, the polymer of the component (B), and the crosslinking agent of the component (C) With respect to 100 parts by mass of the total amount, 0.1 parts by mass to 40 parts by mass of (D) component, and at least one selected from the low molecular weight compound and polymer (A) component, the polymer of the component (B), and the component (C) The cured film formation composition containing 0.01 mass parts - 10 mass parts (E) component, and a solvent with respect to 100 mass parts of the total amount of a crosslinking agent and the compound of (D)component.

The compounding ratio in the case of using the cured film formation composition of this embodiment as a solution, a preparation method, etc. are explained in full detail below.

Although the ratio of solid content in the cured film formation composition of this embodiment is not specifically limited as long as each component is melt|dissolving in the solvent uniformly, It is 1 mass % - 80 mass %, Preferably it is 3 mass % - It is 60 mass %, More preferably, it is 5 mass % - 40 mass %. Here, solid content means what removed the solvent from all the components of a cured film formation composition.

The preparation method of the cured film formation composition of this embodiment is not specifically limited. As a preparation method, (A) component and (C)component, (D)component, further (E)component are mixed in a predetermined ratio with the solution of (B) component dissolved in a solvent, for example, and uniform The method of setting it as a solution, or the method of adding and mixing other additives as needed in a suitable step of this preparation method is mentioned.

In preparation of the cured film formation composition of this embodiment, the solution of the specific copolymer obtained by the polymerization reaction in a solvent can be used as it is. In this case, for example, (A) component, (C)component, (D)component, further (E)component etc. are added to the solution which prepared the (B) component acrylic polymer, and it is set as a uniform solution. At this time, the solvent may be additionally added again for the purpose of adjusting the concentration. At this time, the solvent used in the preparation process of (B) component and the solvent used for density|concentration adjustment of a cured film formation composition may be the same, and may differ.

Moreover, it is preferable to use, after filtering the solution of the prepared cured film formation composition using the filter etc. whose pore diameter is about 0.2 micrometer.

As mentioned above, the cured film formation composition of this embodiment of this invention is selected from (A) a photo-alignment group, a hydroxyl group, a carboxyl group, an amide group, an amino group, an alkoxysilyl group, and group represented by the said Formula (2). At least one selected from a low molecular weight compound having at least one substituent and a polymer, (B) at least one selected from a hydroxyl group, a carboxyl group, an amide group, an amino group, an alkoxysilyl group, and a group represented by the formula (2) It is constituted by containing a polymer having a substituent of (A) In at least one selected from a low molecular weight compound and a polymer, the photo-alignment group constitutes a hydrophobic photoreactive moiety, and a hydroxyl group, a carboxyl group, an amide group, an amino group, an alkoxysilyl group, and the formula (2) At least one substituent selected from the groups represented constitutes a hydrophilic thermal reaction moiety. (B) At least 1 substituent chosen from the hydroxyl group of the polymer of a component, a carboxyl group, an amide group, an amino group, an alkoxysilyl group, and group represented by the said Formula (2) is also hydrophilic.

Therefore, the cured film formed from the cured film formation composition of this embodiment originates in the property of (B) component, and the inside becomes hydrophilic and is formed so that a film|membrane structure may be stabilized. And at least 1 sort(s) chosen from the low molecular weight compound of (A) component in a cured film, and a polymer will become unevenly distributed in the surface vicinity of a cured film. More specifically, at least one selected from the low molecular weight compound and polymer of component (A) has a structure in which the hydrophilic thermally reactive portion faces the inner side of the cured film and the hydrophobic photoreactive portion faces the surface side of the cured film, ubiquitous near the surface. As a result, the cured film of this embodiment will implement|achieve the structure which increased the ratio of the photoreactive group of (A) component which exists in the surface vicinity. And when the cured film of this embodiment is used as an orientation material, the efficiency of the photoreaction for photo-alignment can be improved, and it can have the outstanding orientation sensitivity. Furthermore, it becomes an orientation material suitable for the formation of a patterned retardation material, and a patterned retardation material manufactured using the same may have excellent pattern formability.

Moreover, as above-mentioned, the cured film formation composition of this embodiment contains a crosslinking agent as (C)component. Thereby, in the inside of the cured film obtained from the cured film formation composition of this embodiment, before the photoreaction by the at least 1 sort(s) of photo-alignment group chosen from the low molecular weight compound of (A) component, and a polymer, thermal reaction with (C) a crosslinking agent crosslinking reaction can be carried out by As a result, when used as an orientation material, the tolerance with respect to the polymeric liquid crystal apply|coated thereon or its solvent can be improved.

And the cured film formation composition of this embodiment of this invention is polymerization containing C=C double bond in 1 molecule as (D)component with (A) component, (B) component, and (C)component. A low molecular weight compound having at least one sexual group and at least one N-alkoxymethyl group is contained. (D) When the cured film obtained from the cured film formation composition of this embodiment is used as an orientation material, the compound which is a component functions so that the adhesiveness between the layers of the hardened|cured polymeric liquid crystal formed on it may be reinforced.

<Cured film, alignment material and phase difference material>

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

As the conditions for drying by heating, the curing reaction may proceed to such an extent that the component of the alignment material formed from the cured film does not elute to 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 a heating time appropriately selected from the range of minutes to 60 minutes are employed. The heating temperature and heating time are preferably 70°C to 160°C, 0.5 minutes to 10 minutes.

The film thickness of the cured film formed using the curable composition of this embodiment is 0.05 micrometer - 5 micrometers, for example, Considering the level|step difference of the board|substrate to be used, and an optical and electrical property, it can select suitably.

The cured film formed in this way can function as a member which orientates the compound which has an orientation material, ie, liquid crystal containing a polymeric liquid crystal, etc. by performing polarization|polarized-light UV irradiation.

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

Since the orientation material formed from the cured film composition of this embodiment has solvent resistance and heat resistance, on this orientation material, after apply|coating the retardation material which consists of a polymerizable liquid crystal solution, by heating to the phase transition temperature of the liquid crystal, the retardation material is liquid crystal. It is set as a state and is made to orientate on an orientation material. Then, the retardation material having a desired orientation state is cured as it is, and a retardation material having a layer having optical anisotropy can be formed.

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 board|substrate with which an orientation material is formed is a film, the film which has the retardation material of this embodiment becomes useful as retardation film. The retardation material forming such a retardation material is in a liquid crystal state, and there are some that take an orientation state such as horizontal orientation, cholesteric orientation, vertical orientation, hybrid orientation, etc. on the orientation material, and are classified according to each required retardation characteristic can be used by

In addition, when manufacturing the patterned retardation material used for 3D display, to the cured film formed by the above-mentioned method from the cured film composition of this embodiment, from a predetermined reference|standard through the mask of a line and space pattern, for example For example, polarized UV exposure in a direction of +45 degrees, and then, after removing the mask, polarized UV exposure is exposed in a direction of -45 degrees to form an alignment material in which two types of liquid crystal alignment regions having different orientation control directions of liquid crystal are formed. . After that, the retardation material made of a polymerizable liquid crystal solution is applied, and then the retardation material is brought into a liquid crystal state by heating to the phase transition temperature of the liquid crystal. The polymerizable liquid crystal in the liquid crystal state is aligned on the alignment material in which two types of liquid crystal alignment regions are formed, and an alignment state corresponding to each liquid crystal alignment region is formed. Then, the retardation material in which such an orientation state is realized is cured as it is, and the orientation state described above is fixed, and a patterned retardation material in which two types of retardation regions having different retardation characteristics are arranged regularly and plural, respectively, can be obtained. .

Moreover, the use as a liquid crystal aligning film of a liquid crystal display element is also possible for the orientation material formed from the cured film composition of this embodiment. For example, using two substrates having the alignment material of this embodiment formed as described above, bonding the alignment materials on both substrates through a spacer so that they face each other, and then injecting liquid crystal between these substrates , it is possible to manufacture a liquid crystal display device in which the liquid crystal is aligned.

Thereby, the cured film formation composition of this embodiment can be used suitably for manufacture of various retardation materials (retardation film), a liquid crystal display element, etc.

[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 ingredients used in Examples and their abbreviations]

Each composition component used in the following Examples and Comparative Examples is as follows. In the following formula, Me represents a methyl group and t-Bu represents a tert-butyl group.

<Component (A): Low-molecular photo-alignment component>

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

[Formula 21]

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

[Formula 22]

CIN3: 4-[4-(6-hydroxyhexyloxy)benzoyl]cinnamic acid tertbutyl ester

[Formula 23]

CIN4: 4-(6-methacryloxyhexyl-1-oxy)cinnamic acid

[Formula 24]

CIN5: 4-propyloxycinnamic acid

[Formula 25]

<Specific polymer raw material>

MAA: methacrylic acid

MMA: methyl methacrylate

HEMA: 2-hydroxyethyl methacrylate

CIN4: 4-(6-methacryloxyhexyl-1-oxy)cinnamic acid

AIBN: α,α′-azobisisobutyronitrile

<Component (B)>

PEPO: polyester polyol polymer (adipic acid/diethylene glycol copolymer having the following structural unit, molecular weight 4,800.)

[Formula 26]

(In the formula, R represents alkylene.)

<Component (C): Crosslinking Agent>

HMM: Hexamethoxymethylmelamine

<Component (E): Cross-linking catalyst>

PTSA: paratoluenesulfonic acid

[Formula 27]

<Component (D): Low molecular weight compound having N-alkoxymethyl group and polymerizable group>

D-1: N-methoxymethylmethacrylamide

[Formula 28]

D-2: N-methoxymethylacrylamide

[Formula 29]

D-3: N-n-butoxymethylacrylamide (BMAA)

[Formula 30]

D-4: N-isobutoxymethylacrylamide

[Formula 31]

D-5:

[Formula 32]

D-6:

[Formula 33]

<Other reagents>

BHT: 2,6-di-tertbutyl-para-cresol

DBU: 1,8-diazabicyclo[5.4.0]-7-undecene

<solvent>

Each cured film formation composition of an Example and a comparative example contained a solvent, propylene glycol monomethyl ether (PM), butyl acetate (BA), and methyl ethyl ketone (MEK) were used as the solvent.

<Measurement of molecular weight of polymer>

The molecular weight of the polyimide, polyamic acid, or acrylic polymer in the synthesis example was measured using a room temperature gel permeation chromatography (GPC) apparatus (GPC-101) manufactured by Shodex Corporation, and a column (KD-803, KD-805) manufactured by Shodex Corporation. It was used and measured as follows.

Column temperature: 50℃

Eluent: N,N-dimethylformamide (as an additive, lithium bromide-hydrate (LiBr H ₂ O) is 30 mmol/L, phosphoric acid/anhydrous crystal (o-phosphoric acid) is 30 mmol/L, tetrahydrofuran (THF) is 10mL/L)

Flow rate: 1.0 mL/min

Standard samples for calibration curve preparation: TSK standard polyethylene oxide (molecular weights about 900,000, 150,000, 100,000, 30,000) manufactured by Tosoh Corporation, and polyethylene glycol manufactured by Polymer Laboratory (molecular weights of about 12,000, 4,000, 1,000).

<Examples and Comparative Examples>

<Polymerization Example 1>

3.5 g of MAA, 7.0 g of MMA, 7.0 g of HEMA, and 0.5 g of AIBN as a polymerization catalyst were dissolved in 53.9 g of PM and reacted at 70° C. for 20 hours to obtain an acrylic copolymer solution (solid content concentration of 25 mass%) (P1). Mn of the obtained acrylic copolymer was 10,300 and Mw was 24,600.

<Polymerization Example 2>

100.0 g of MMA, 11.1 g of HEMA, and 5.6 g of AIBN as a polymerization catalyst were dissolved in 450.0 g of PM and reacted at 80° C. for 20 hours to obtain an acrylic copolymer solution (solid content concentration: 20 mass%) (P2). Mn of the obtained acrylic copolymer was 4,200, and Mw was 7,600.

<Polymerization Example 3>

100.0 g of Nn-butoxymethylacrylamide (BMAA) and 4.2 g of AIBN as a polymerization catalyst were dissolved in 193.5 g of PM, and reacted at 90° C. for 20 hours to obtain an acrylic polymer solution (solid content concentration: 35 mass%) (P3). Mn of the obtained acrylic copolymer was 2,700, and Mw was 3,900.

<Polymerization Example 4>

CIN 4 4.0 g, styrene 4.0 g, HEMA 2.0 g, and 0.1 g of AIBN as a polymerization catalyst were dissolved in PM 90.9 g and reacted at 80° C. for 20 hours to obtain an acrylic polymer solution (solid content concentration: 10 mass%) (CIN6). Mn of the obtained acrylic copolymer was 20,000, and Mw was 55,000.

Synthesis of compound [D-5]

[Formula 34]

In a nitrogen stream, 500 g of ethyl acetate, 35.5 g (0.300 mol) of 1,6-hexanediol, 1.80 g of 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) in a 2L four-necked flask (11.8 mmol), 0.45 g (2.04 mmol) of 2,6-di-tertbutyl-para-cresol (BHT) was added at room temperature, and the temperature was raised to 55° C. under magnetic stirrer stirring. To the reaction solution, 95.9 g (0.679 mol) of 2-isocyanatoethyl acrylate was added dropwise, and after stirring for 2 hours, the reaction solution was analyzed by high-performance liquid chromatography, and the reaction was performed when the intermediate became 1% or less in area percentage. has been completed After adding 328 g of hexane and cooling to room temperature, the precipitated solid was washed twice with 229 g of hexane and dried to obtain compound [Aa] (104 g, 0.260 mol, yield 86.7%).

[Formula 35]

In a nitrogen stream, 1330 g of dichloromethane, 100 g (0.250 mol) of compound [Aa], and 22.5 g (0.749 mol) of paraformaldehyde were put into a 2L four-necked flask, and 122 g (1.12 mol) of trimethylsilyl chloride was added in an ice bath. was dropped. After stirring for 2 hours, a mixture of 63.2 g (0.625 mol) of triethylamine and 240 g of methanol was added dropwise. After stirring for 30 minutes, it was transferred to a 5 L separatory funnel, and 1500 g of water was added to perform a liquid separation operation. The obtained organic layer was dried over magnesium sulfate, magnesium sulfate was removed by filtration, and the resulting filtrate was concentrated and dried to obtain compound [D-5] (110 g, 0.226 mol, yield 90.3%). The structure of compound [D-5] was confirmed by obtaining the following spectral data by ^{1 H-NMR analysis.}

¹ H-NMR (CDCl ₃ ): δ6.42 (d,2H J=17.2), 6.17-6.08 (m,2H), 5.86 (d,2H J=10.0), 4.77 (d,4H J=19.6), 4.30(m,4H),4.12(t,4H J=6.4),3.61(m,4H), 3.30(d,6H J=12.8),1.67(m,4H),1.40(m,4H).

Synthesis of compound [D-6]

[Formula 36]

In a nitrogen stream, 35.0 g of ethyl acetate, 87.0 g of toluene, 8.41 g (50.0 mmol) of hexamethylene diisocyanate, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU) in a 500 mL four-necked flask under a nitrogen stream. ) 0.345 g (2.27 mmol), 70.0 mg (0.318 mmol) of 2,6-di-tertbutyl-para-cresol (BHT) was added at room temperature, and the temperature was raised to 60° C. under magnetic stirrer stirring. A liquid mixture of 12.8 g (111 mmol) of 2-hydroxyethyl acrylate and 26.0 g of toluene was added dropwise to the reaction solution, followed by stirring for 1 hour, followed by stirring at room temperature for 24 hours. After adding 131 g of hexane and cooling by immersion in an ice bath, the precipitated crystals were filtered and dried to obtain compound [Ab] (15.0 g, 37.4 mmol, yield 74.8%).

[Formula 37]

In a nitrogen stream, 200 g of dichloromethane, 14.6 g (36.4 mmol) of compound [Ab], and 3.28 g (0.109 mmol) of paraformaldehyde were put into a 300 mL four-neck flask, and in an ice bath, 23.7 g (0.218 mmol) of trimethylsilyl chloride ) was added dropwise. After stirring for 1 hour, 35.6 g of methanol was added dropwise, followed by stirring for 1 hour. The organic layer was washed with 300 mL of a saturated aqueous sodium bicarbonate solution, and the obtained aqueous layer was washed again with 200 g of dichloromethane. The solution obtained by mixing these two organic layers was washed again with 170 g of brine, and the resulting organic layer was dried over magnesium sulfate. Magnesium sulfate was removed by filtration, and the obtained dichloromethane solution was concentrated and dried to obtain the desired [D-6] (16.2 g, 33.1 mmol, yield 91.0%).

The structure of compound [D-6] was confirmed by obtaining the following spectral data by ^{1 H-NMR analysis.}

¹ H-NMR (CDCl ₃ ): δ6.33 (d,2H J=17.2), 6.20-6.14 (m, 2H), 5.96 (d, 2H J=10.4), 4.63 (s, 4H), 4.33 (m) ,4H),4.27(m,4H),3.16-3.14(br,10H),1.47(m,4H),1.20(m,4H).

<Preparation of base film>

The acrylic film used as a base material can be created by the following method, for example. That is, raw material pellets made of a copolymer containing methyl methacrylate as a main component are melted at 250° C. by an extruder, passed through a T-die, and an acrylic film having a thickness of 40 μm can be prepared through casting rolls and drying rolls. TAC film can be prepared in the same way.

<Examples 1 to 18, Comparative Examples 1 to 2>

Each cured film formation composition of an Example and a comparative example was prepared with the composition shown in Table 1, and orientation, pattern formation property, and adhesiveness were evaluated about each.

[Table 1]

[Evaluation of orientation]

After apply|coating each cured film formation composition of an Example and a comparative example on a film using a bar coater, it heat-dried in the heat circulation type oven at the temperature of 110 degreeC for 2 minutes, and formed the cured film. 313 nm linearly polarized light was vertically irradiated to each of these cured films at 10 mJ/cm<^2> exposure amount, and the orientation material was formed. On the alignment material on the substrate, a 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 board|substrate ^{was exposed at 300 mJ/cm<2>} , and the retardation material was produced. The retardation material on the produced substrate was sandwiched between a pair of polarizing plates, and the state of expression of the retardation characteristics in the retardation material was observed. It described in the column of "Orientation property".

[Evaluation of pattern formability]

Each cured film-forming composition of Examples and Comparative Examples was applied on an acrylic film or TAC film using a bar coater, and then dried by heating in a thermal cycle oven at a temperature of 110° C. for 2 minutes to form a cured film. The cured film was irradiated with 313 nm linearly polarized light 20 mJ/cm ^{2 perpendicularly through a 350 µm line and space mask.} Next, the mask was removed, the substrate was rotated by 90 degrees, and then linearly polarized light of 313 nm ^{was irradiated vertically at 10 mJ/cm 2} , and an alignment material in which two types of liquid crystal alignment regions in which the orientation control direction of liquid crystals were different by 90 degrees was formed was obtained. . On the alignment material on the substrate, a 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 board|substrate ^{was exposed at 300 mJ/cm<2>} , and the patterned retardation material in which two types of areas|regions which have different retardation characteristics were regularly arranged were produced. Observe the patterned retardation material on the produced substrate using a polarization microscope, indicate that there is no alignment defect and a retardation pattern is formed, as ○, and if there is an orientation defect, ×, write in the column of “Pattern formation” in Table 2 did

[Evaluation of adhesion]

Each cured film-forming composition of Examples and Comparative Examples was applied on an acrylic film or TAC film using a bar coater, and then dried by heating in a thermal cycle oven at a temperature of 110° C. for 2 minutes to form a cured film. The cured film was irradiated with 313 nm linearly polarized light 20 mJ/cm ^{2 perpendicularly through a 350 µm line and space mask.} Next, the mask was removed, the substrate was rotated by 90 degrees, and then linearly polarized light of 313 nm ^{was irradiated vertically at 10 mJ/cm 2} , and an alignment material in which two types of liquid crystal alignment regions in which the orientation control direction of liquid crystals were different by 90 degrees was formed was obtained. . On the alignment material on the substrate, a 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 board|substrate ^{was exposed at 300 mJ/cm<2>} , and the patterned retardation material in which two types of areas|regions which have different retardation characteristics were regularly arranged were produced.

In this patterned phase difference material, cuts were made with a cutter knife so as to have a 5x5 scale at intervals of 1 mm in length and width. A cellophane tape peeling test was performed on this sheath using a scotch tape. An evaluation result was made into "initial stage", and the thing which remained without peeling all 25 divisions was made into (circle), and the thing which peeled even 1 division|division was made into x. An evaluation result is put together in Table 2 and shown later.

[Evaluation of durability and adhesion]

The retardation material on the acrylic film or TAC film produced by the same method as for the evaluation of the adhesiveness described above was placed in an oven set at a temperature of 80°C and a humidity of 90%, and left still for 72 hours or more. Then, the phase difference material was taken out and adhesiveness was evaluated by the method similar to evaluation of adhesiveness mentioned above. An evaluation result is put together in Table 2 as "durability", and is shown.

[Result of evaluation]

As mentioned above, the result of having performed the above evaluation is shown in Table 2.

[Table 2]

The orientation material obtained using the cured film formation composition of Examples 1-18 showed favorable orientation similarly to the orientation material obtained using the cured film formation composition of a comparative example.

Moreover, the orientation material obtained using the cured film formation composition of Examples 1-18 showed favorable pattern formation similarly to the orientation material obtained using the cured film formation composition of a comparative example.

Furthermore, the cured film obtained using the cured film formation composition of Examples 1-18 maintained high adhesiveness even if it carried out high temperature, high humidity process, and showed the outstanding adhesion durability.

On the other hand, it was difficult for the cured film obtained using the cured film formation composition of a comparative example to maintain initial stage adhesiveness after a high temperature, high humidity process.

[Industrial Applicability]

The cured film-forming composition according to the present invention is very useful as an alignment material for forming a liquid crystal alignment film of a liquid crystal display device or an optically anisotropic film provided inside or outside a liquid crystal display device, in particular, patterning retardation of 3D display It is suitable as a material for forming ashes. Furthermore, materials for forming cured films such as protective films, flattening films and insulating films in various displays such as thin film transistor (TFT) liquid crystal display elements and organic EL elements, in particular, interlayer insulating films of TFT-type liquid crystal elements, 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 low molecular weight compound having at least one substituent selected from the group consisting of a photo-alignment group, a hydroxyl group, a carboxyl group, an amide group, an amino group, an alkoxysilyl group, and a group represented by the following formula (2) And a photo-alignment group, a hydride At least one selected from a polymer having at least one substituent selected from the group consisting of a hydroxy group, a carboxyl group, an amide group, an amino group, an alkoxysilyl group, and a group represented by the following formula (2);

(In the formula, R ⁶² represents an alkyl group, an alkoxy group, or a phenyl group.)
(B) a polymer having at least one substituent selected from the group consisting of a hydroxyl group, a carboxyl group, an amide group, an amino group, an alkoxysilyl group, and a group represented by the formula (2);
(C) a crosslinking agent, and
(D) a low molecular weight compound having at least one polymerizable group containing a C=C double bond in one molecule and at least one N-alkoxymethyl group
A cured film forming composition comprising:
According to claim 1,
Component (A) is a photo-alignment group, a low molecular weight compound having at least one of a hydroxyl group and a carboxyl group, and a polymer having at least one of a photo-alignment group, a hydroxyl group and a carboxyl group. forming composition.
According to claim 1,
(D) The cured film formation composition whose component is a compound which has a structure represented by following formula (1).

(Wherein, R ¹ represents a hydrogen atom or a methyl group, and R ² represents a hydrogen atom or a straight-chain or branched-chain alkyl group having 1 to 10 carbon atoms.)
According to claim 1,
(D) The cured film formation composition whose component is a compound which has a structure represented by a following formula (X2).

[Wherein, R ⁵¹ represents a hydrogen atom or a methyl group. R ⁵³ is each independently a linear or branched alkylene group having 2 to 20 carbon atoms, a divalent group consisting of an aliphatic ring having 5 to 6 carbon atoms, or a divalent aliphatic group including an aliphatic ring having 5 to 6 carbon atoms and may contain an ether bond in the structure of these groups. R ⁵⁴ is a divalent to 9 valent group having a structure in which an additional 1 to 8 hydrogen atoms are removed from a linear or branched alkyl group having 2 to 20 carbon atoms, or a hydrogen atom from an alicyclic group having 5 to 6 carbon atoms A divalent to 9-valent group having a structure in which 1 to 8 are removed, or a divalent to 9-valent aliphatic group including an aliphatic ring having 5 to 6 carbon atoms is represented, and an ether bond may be included in the structure. R ⁵² represents a linear or branched monovalent group consisting of an alkyl group having 1 to 20 carbon atoms, an aliphatic ring having 5 to 6 carbon atoms, or a monovalent aliphatic group including an aliphatic ring having 5 to 6 carbon atoms, these groups One of the methylene groups or a plurality of non-adjacent methylene groups may be substituted for the ether bond. Z is >NCOO- or -OCON< (where "-" represents one bond. In addition, ">" and "<" represent two bonds. One bond of N atoms is -CH ₂ OR ⁵² is bonded.). r is a natural number between 2 and 9.]
According to claim 1,
(E) A crosslinking catalyst is contained, The cured film formation composition characterized by the above-mentioned.
It is obtained using the cured film formation composition in any one of Claims 1-5, The orientation material characterized by the above-mentioned.
It has a cured film obtained from the cured film formation composition in any one of Claims 1-5, The retardation material characterized by the above-mentioned.