KR20190031216A - Composition and optical film - Google Patents

Abstract

A purpose of the present invention to provide a composition for manufacturing an optical film exhibiting excellent adhesion properties between a substrate or a polarizing film and an optical film, and the optical film manufactured by using the composition. The present invention provides a composition comprising the composition comprising: (A) a polymerizable liquid crystal compound; (B) a compound having a carbon-carbon unsaturated bond and an active hydrogen-reactive group in a molecule; and (c) a photopolymerization initiator, wherein the (B) is preferably a compound having an isocyanato group as an active hydrogen-reactive group.

Description

COMPOSITION AND OPTICAL FILM < RTI ID = 0.0 >

The present invention relates to compositions and optical films.

In a flat panel display (FPD), a member including an optical film such as a polarizing plate and a retardation film is used. As an optical film, it is known that the optical film is produced by applying a composition comprising a polymerizable liquid crystal compound, a photopolymerization initiator and a solvent onto a substrate. For example, Patent Document 1 discloses an optical film formed by applying a composition on a substrate subjected to alignment treatment to obtain a coating film, orienting the polymerizable liquid crystal compound contained in the coating film, and polymerizing the polymerizable liquid crystal compound .

(Patent Document 1) Patent Document 1: Japanese Patent Application Laid-Open No. 2007-148098

The present invention includes the following inventions.

[1] A composition comprising (A), (B) and (C)

(A) a polymerizable liquid crystal compound

(B) a compound having a carbon-carbon unsaturated bond and an active hydrogen-reactive group in the molecule

(C) a photopolymerization initiator

[2] The composition according to [1], wherein (B) is a compound having an isocyanato group as an active hydrogen-reactive group.

[3] The composition according to [1], wherein (B) is a compound represented by the following formula (X).

[In the formula (X)

n represents an integer of 1 to 10, and R ^{1 '} represents a divalent aliphatic or alicyclic hydrocarbon group having 2 to 20 carbon atoms or a divalent aromatic hydrocarbon group having 5 to 20 carbon atoms. The two R ^{2 '} groups in each repeating unit are -NH- on one side and the group represented by - [NC (═O) -R ^3' ] - on the other. R ^{3 '} represents a group having a hydroxyl group or a carbon-carbon unsaturated bond.

Among R ^{3 '} in the formula (X), at least one R ^3' is a group having a carbon-carbon unsaturated bond.

[4] The composition according to any one of [1] to [3], wherein (A) is a compound represented by the formula (A)

[In the formula (A)

X ¹ represents an oxygen atom, a sulfur atom or -NR ¹ -. R ¹ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

Y ¹ represents a monovalent aromatic hydrocarbon group having 6 to 12 carbon atoms, which may have a substituent, or a monovalent aromatic heterocyclic group having 3 to 12 carbon atoms, which may have a substituent.

Q ³ and Q ⁴ each independently represent a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, a monovalent group having 6 to 20 carbon atoms An aromatic hydrocarbon group, a halogen atom, a cyano group, a nitro group, -NR ² R ³ or -SR ² , or Q ³ and Q ⁴ are bonded to each other to form an aromatic ring or aromatic heterocyclic ring . R ² and R ³ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

D ¹ and D ² are each independently a single bond, -C (= O) -O-, -C (= S) -O-, -CR 4 R 5 -, -CR 4 R 5 -CR 6 R 7 - -O-CR ⁴ R ⁵ -, -CR ⁴ R ⁵ -O-CR ⁶ R ⁷ -, -CO-O-CR ⁴ R ⁵ -, -O-CO-CR ⁴ R ⁵ -, -CR ⁴ R ⁵ -O-CO-CR ⁶ R ⁷ -, -CR ⁴ R ⁵ -CO-O-CR ⁶ R ⁷ - or -NR ⁴ -CR ⁵ R ⁶ - or -CO-NR ⁴ -.

R ⁴ , R ⁵ , R ⁶ and R ⁷ each independently represent a hydrogen atom, a fluorine atom or an alkyl group having 1 to 4 carbon atoms.

G ¹ and G ² each independently represent a divalent alicyclic hydrocarbon group having 5 to 8 carbon atoms, and the methylene group constituting the alicyclic hydrocarbon group may be substituted with an oxygen atom, a sulfur atom or -NH-, and the alicyclic hydrocarbon The methine group constituting the group may be substituted with a tertiary nitrogen atom.

L ¹ and L ² each independently represent a monovalent organic group, and at least one of L ¹ and L ² is an organic group having a polymerizable group.

[5] (A) indicates that. The composition according to [4], wherein L ^{1 in} formula (A) is a group represented by formula (A1) and L ² is a group represented by formula (A2).

P ¹ -F ¹ - (B ¹ -A ¹ ) _k -E ¹ - (A1)

P ² -F ² - (B ² -A ² ) ₁ -E ² - (A2)

[In the formulas (A1) and (A2)

B ¹ , B ² , E ¹ and E ² are each independently -CR ⁴ R ⁵ -, -CH ₂ -CH ₂ -, -O-, -S-, -CO-O-, -O-CO-O -, -CS-O-, -O-CS-O-, -CO-NR ¹ -, -O-CH ₂ -, -S-CH ₂ - or a single bond.

A ¹ and A ² each independently represent a divalent alicyclic hydrocarbon group having 5 to 8 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms and the methylene group constituting the alicyclic hydrocarbon group is an oxygen atom, -, and the methine group constituting the alicyclic hydrocarbon group may be substituted with a tertiary nitrogen atom.

k and l each independently represent an integer of 0 to 3; When k is an integer of 2 or more, plural B ^{1 s} may be the same or different, and plural A ^{1 s} may be the same or different. When l is an integer of 2 or more, the plurality of B ² may be the same or different, and the plurality of A ² may be the same or different.

F ¹ and F ² represent a divalent aliphatic hydrocarbon group having 1 to 12 carbon atoms.

P ¹ represents a polymerizable group.

P ² represents a hydrogen atom or a polymerizable group.

R ¹ , R ⁴ and R ⁵ have the same meaning as above.]

[6] An optical film formed by polymerizing a polymerizable liquid crystal compound contained in the composition described in any one of [1] to [5].

[7] A process for producing an optical film comprising the following (1) and (2).

(1) a step of applying the composition described in any one of [1] to [5] onto a substrate;

(2) a step of forming an optical film by polymerizing the polymerizable liquid crystal compound contained in the coating film applied on the substrate by (1)

[8] The method for producing an optical film according to [7], wherein the substrate is made of a material having a hydroxyl group.

[9] The process for producing an optical film according to [8], wherein the material having a hydroxyl group is a material obtained by saponifying triacetyl cellulose.

[10] The method for producing an optical film according to any one of [7] to [9], wherein the substrate is provided with an alignment film formed on the surface thereof with a photo-orientable polymer.

[11] The method for producing an optical film according to [10], wherein the alignment film is formed by forming a crosslinking structure by photoirradiation of a photo-orientable polymer.

[12] An optical film obtained by the production method described in any one of [7] to [11].

[13] An optical film according to [6] or [12] having a retardation.

[14] A polarizing plate comprising the optical film according to [6], [12] or [13].

[15] A flat panel display device comprising an optical film according to [6], [12] or [13].

[16] A composition comprising (D) and (B)

(D) photo-orientable polymer

(B) a compound having a carbon-carbon unsaturated bond and an active hydrogen-reactive group in the molecule

[17] The composition according to [16], wherein (D) is a photo-orientable polymer capable of forming a crosslinked structure by light irradiation.

[18] The composition according to [16] or [17], wherein (B) is a compound having an isocyanato group as an active hydrogen-reactive group.

[19] The composition according to [16] or [17], wherein (B) is a compound represented by the following formula (X).

[In the formula (X)

n represents an integer of 1 to 10, and R ^{1 '} represents a divalent aliphatic or alicyclic hydrocarbon group having 2 to 20 carbon atoms or a divalent aromatic hydrocarbon group having 5 to 20 carbon atoms. And two R ^{2 '} in each repeating unit are groups represented by --NH- on one side and - [NC (═O) -R ^3' ] - on the other. R ^{3 '} represents a group having a hydroxyl group or a carbon-carbon unsaturated bond.

Among R ^{3 '} , at least one R ^3' is a group having a carbon-carbon unsaturated bond.

[20] An optical film formed by crosslinking a photo-orientable polymer contained in the composition described in any one of [16] to [19].

[21] A method for producing an optical film comprising the following (1) and (2).

(1) a step of applying the composition described in any one of [16] to [19] on a substrate;

(2) a step of forming an optical film by crosslinking the photo-orientable polymer contained in the coating film applied on the substrate by (1)

[22] The process for producing an optical film according to [21], wherein the substrate is made of a material having a hydroxyl group.

[23] The production method of an optical film according to [22], wherein the material having a hydroxyl group is a material obtained by saponifying triacetyl cellulose.

[24] An optical film obtained by the production method described in any one of [21] to [23].

[25] A retardation film formed by further forming an optically anisotropic layer on an optical film according to [20] or [24].

[26] A polarizing plate comprising the optical film according to [20] or [24].

[27] A flat panel display device comprising an optical film according to [20] or [24].

[28] An optical film comprising a substrate, an A layer formed from the composition (A), and a B layer formed from the composition (B) in this order,

Wherein the composition (A) contains the following (D) and (B-1) and the composition (B) contains the following (A), (B-2) and (C).

(D) photo-orientable polymer

(B-1) a compound having a carbon-carbon unsaturated bond and an active hydrogen-reactive group

(A) a polymerizable liquid crystal compound

(B-2) a compound having a carbon-carbon unsaturated bond and an active hydrogen-reactive group

(C) a photopolymerization initiator

[29] An optical film according to [28], wherein (D) is a photo-orientable polymer capable of forming a crosslinked structure by light irradiation.

[30] The composition according to [28] or [29], wherein (B-1) and (B-2) are both compounds having an isocyanato group as an active hydrogen-reactive group.

[31] The optical film described in [28] or [29], wherein (B-1) and (B-2) are each independently a compound represented by the following formula (X).

[In the formula (X)

n represents an integer of 1 to 10, and R ^{1 '} represents a divalent aliphatic or alicyclic hydrocarbon group having 2 to 20 carbon atoms or a divalent aromatic hydrocarbon group having 5 to 20 carbon atoms. The two R ^{2 '} groups in each repeating unit are -NH- on one side and the group represented by - [NC (═O) -R ^3' ] - on the other. R ^{3 '} represents a group having a hydroxyl group or a carbon-carbon unsaturated bond.

Among R ^{3 '} , at least one R ^3' is a group having a carbon-carbon unsaturated bond.

[32] The optical film described in any one of [28] to [31], wherein the layer A is formed by crosslinking (D) contained in the composition (A).

[33] The optical film described in any one of [28] to [32], wherein the substrate is made of a material having a hydroxyl group.

[34] The optical film according to [33], wherein the material having a hydroxyl group is a material obtained by saponifying triacetyl cellulose.

[35] The optical film described in any one of [28] to [34], which has a retardation.

[36] A process for producing an optical film comprising the steps of <1> to <4> below.

&Lt; 1 > A method for producing a film, comprising: a step of forming a first coating film on a substrate by applying a composition (A) containing the following (D) and (B-1)

(D) photo-orientable polymer

(B-1) a compound having a carbon-carbon unsaturated bond and an active hydrogen-reactive group

(2) a step of converting the first coating film into an A-layer by crosslinking (D) contained in the first coating film applied on the substrate by <1>;

<3> A composition (B) containing the following (A), (B-2) and (C) is applied on the layer A formed by <2> to form a second coating film on the layer A fair;

(A) a polymerizable liquid crystal compound

(B-2) a compound having a carbon-carbon unsaturated bond and an active hydrogen-reactive group

(C) a photopolymerization initiator

&Lt; 4 > A process for polymerizing a polymerizable liquid crystal compound contained in a second coating film formed by < 3 >

[37] An optical film obtained by the production method described in [36].

[38] A polarizing plate comprising the optical film according to any one of [28] to [35] or [37].

[39] A flat panel display device comprising the optical film according to any one of [28] to [35] or [37].

1 is a schematic cross-sectional view showing an example of a polarizing plate according to the present invention.
2 is a schematic cross-sectional view showing an example of a liquid crystal display device according to the present invention.
3 is a schematic cross-sectional view showing an example of an organic EL display device according to the present invention.

I. First Embodiment of the Present Invention

1. The first composition of the present invention (hereinafter, the first composition of the present invention is referred to as &quot; present composition (1) &quot;, and the optical film produced by this composition (1) 1) ")

(A) a polymerizable liquid crystal compound, (B) a compound having a carbon-carbon unsaturated bond and an active hydrogen-reactive group in the molecule (hereinafter referred to as &quot; compound (B) &quot; And a photopolymerization initiator.

1-1. The compound (B)

The compound (B) has a carbon-carbon unsaturated bond and an active hydrogen-reactive group in its molecule. The term "active hydrogen-reactive group" means a group having reactivity with a group having an active hydrogen such as a carboxyl group (-COOH), a hydroxyl group (-OH), or an amino group (-NH ₂ ), and includes a glycidyl group, An imidazo group, a thioisocyanato group, a maleic anhydride group, and the like. The number of carbon-carbon unsaturated bonds and active hydrogen reactive groups of Compound (B) is 1 to 20, preferably 1 to 10, respectively.

The compound (B) is preferably at least two active hydrogen reactive groups. The plural active hydrogen-reactive groups may be the same or different.

The carbon-carbon unsaturated bond of the compound (B) may be a carbon-carbon double bond or a carbon-carbon triple bond or a combination thereof, but is preferably a carbon-carbon double bond. Among them, a vinyl group and / or a (meth) acryl group is preferable. The active hydrogen-reactive group is preferably at least one selected from the group consisting of an epoxy group, a glycidyl group and an isocyanato group, and a compound (B) having an acryl group and an isocyanato group is particularly preferable.

Specific examples of the compound (B) include compounds having a (meth) acryl group and an epoxy group such as methacryloxy glycidyl ether and acryloxy glycidyl ether; Compounds having (meth) acrylic groups and oxetane groups such as oxetane acrylate and oxetane methacrylate; A compound having a (meth) acryl group and a lactone group such as lactone acrylate or lactone methacrylate; A compound having a vinyl group and an oxazoline group such as vinyl oxazoline or isopropenyl oxazoline; Oligomers of a compound having an isocyanato group and a (meth) acryl group such as isocyanatomethyl acrylate, isocyanatomethyl methacrylate, 2-isocyanatoethyl acrylate and 2-isocyanatoethyl methacrylate, etc. . In addition, a compound having a vinyl group such as methacrylic anhydride, acrylic acid anhydride, maleic anhydride and vinyl maleic anhydride, and a vinylene group and an acid anhydride. Among them, methacryloylglycidyl ether, acryloxyglycidyl ether, isocyanatomethyl acrylate, isocyanatomethylmethacrylate, vinyloxazoline, 2-isocyanatoethyl acrylate, 2-isocyanate Nattoethyl methacrylate and oligomers are preferred, and isocyanatomethyl acrylate, 2-isocyanatoethyl acrylate and oligomers are particularly preferred.

The preferred compound (B) is represented by the following formula (X), for example.

[In the formula (X)

n represents an integer of 1 to 10, and R ^{1 '} represents a divalent aliphatic or alicyclic hydrocarbon group having 2 to 20 carbon atoms or a divalent aromatic hydrocarbon group having 5 to 20 carbon atoms. The two R ^{2 '} groups in each repeating unit are -NH- on one side and the group represented by - [NC (═O) -R ^3' ] - on the other. R ^{3 '} represents a group having a hydroxyl group or a carbon-carbon unsaturated bond.

Among R ^{3 '} in the formula (X), at least one R ^3' is a group having a carbon-carbon unsaturated bond.

Among compounds (B) represented by the formula (X), a compound represented by the following formula (XX) (hereinafter sometimes referred to as "compound (XX)") is particularly preferable being).

The compound (XX) can be used as it is or in a purified form according to need, which is commercially available on the market. Commercially available products include, for example, Laromer (registered trademark) LR-9000 (manufactured by BASF).

The content of the compound (B) in the present composition (1) is preferably 0.01 to 10 mass%, more preferably 0.1 to 5 mass%, based on the total mass of the composition (1).

1-2. The polymerizable liquid crystal compound

The polymerizable liquid crystal compound is a compound having a polymerizable group and exhibiting a liquid crystal state. The polymerizable group means a group participating in the polymerization reaction of the polymerizable liquid crystal compound.

One suitable example of the polymerizable liquid crystal compound is, for example, a compound represented by the formula (A) (hereinafter referred to as &quot; compound (A) &quot;

[In the formula (A)

X ¹ represents an oxygen atom, a sulfur atom or -NR ¹ -. R ¹ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

Y ¹ represents a monovalent aromatic hydrocarbon group having 6 to 12 carbon atoms, which may have a substituent, or a monovalent aromatic heterocyclic group having 3 to 12 carbon atoms, which may have a substituent.

Q ³ and Q ⁴ each independently represent a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, a monovalent group having 6 to 20 carbon atoms An aromatic hydrocarbon group, a halogen atom, a cyano group, a nitro group, -NR ² R ³ or -SR ² , or Q ³ and Q ⁴ are bonded to each other to form an aromatic ring or aromatic heterocyclic ring . R ² and R ³ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

D ¹ and D ² are each independently a single bond, -C (= O) -O-, -C (= S) -O-, -CR 4 R 5 -, -CR 4 R 5 -CR 6 R 7 - -O-CR ⁴ R ⁵ -, -CR ⁴ R ⁵ -O-CR ⁶ R ⁷ -, -CO-O-CR ⁴ R ⁵ -, -O-CO-CR ⁴ R ⁵ -, -CR ⁴ R ⁵ -O-CO-CR ⁶ R ⁷ -, -CR ⁴ R ⁵ -CO-O-CR ⁶ R ⁷ - or -NR ⁴ -CR ⁵ R ⁶ - or -CO-NR ⁴ -.

R ⁴ , R ⁵ , R ⁶ and R ⁷ each independently represent a hydrogen atom, a fluorine atom or an alkyl group having 1 to 4 carbon atoms.

G ¹ and G ² each independently represent a divalent alicyclic hydrocarbon group having 5 to 8 carbon atoms, and the methylene group constituting the alicyclic hydrocarbon group may be substituted with an oxygen atom, a sulfur atom or -NH-, and the alicyclic hydrocarbon The methine group constituting the group may be substituted with a tertiary nitrogen atom.

L ¹ and L ² each independently represent a monovalent organic group, and at least one of L ¹ and L ² is an organic group having a polymerizable group.

Examples of the alkyl group having 1 to 4 carbon atoms represented by R ¹ include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group and a sec-butyl group. Among them, an alkyl group having 1 to 3 carbon atoms is preferable, a methyl group and an ethyl group are more preferable, and a methyl group is particularly preferable.

Examples of the aromatic hydrocarbon group represented by Y ¹ include a monocyclic aromatic hydrocarbon group such as a phenyl group; And polycyclic aromatic hydrocarbon groups (including condensed polycyclic aromatic hydrocarbon groups) such as naphthyl group, anthryl group, phenanthryl group and biphenyl group. Among them, as the aromatic hydrocarbon group represented by Y ¹ , a phenyl group and a naphthyl group are preferable, and a phenyl group is more preferable.

Examples of the aromatic heterocyclic group represented by Y ¹ include a monocyclic aromatic heterocyclic group such as a furyl group, a pyrrolyl group, a thienyl group, a pyridinyl group and a thiazolyl group; Aromatic heterocyclic group containing at least one hetero atom such as a nitrogen atom, an oxygen atom and a sulfur atom, such as a polycyclic aromatic heterocyclic group (including a condensed polycyclic aromatic heterocyclic group) such as benzothiazolyl group, benzofuryl group and benzothienyl group, And a heterocyclic group. Among them, a furyl group, thienyl group, thiazolyl group, benzothiazolyl group, benzofuryl group and benzothienyl group are preferable.

The aromatic hydrocarbon group and aromatic heterocyclic group represented by Y ¹ may have a substituent (hereinafter sometimes referred to as "substituent Z ¹ "). The substituent Z ^{1 is preferably a} halogen atom, an alkyl group having 1 to 6 carbon atoms, a cyano group, a nitro group, a nitroso group, a carboxy group, an alkylsulfinyl group having 1 to 6 carbon atoms, an alkylsulfonyl group having 1 to 6 carbon atoms, Alkyl group, an alkoxy group having 1 to 6 carbon atoms, an alkylsulfanyl group having 1 to 6 carbon atoms, an N-alkylamino group having 1 to 6 carbon atoms, an N, N-dialkylamino group having 2 to 12 carbon atoms, A sulfamoyl group, and an N, N-dialkyl sulfamoyl group having 2 to 12 carbon atoms.

Of the substituent Z ¹ , examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a fluorine atom, a chlorine atom and a bromine atom are preferable.

Specific examples of the alkyl group in the substituent Z ¹ include those exemplified as the alkyl group of R ¹ . Among them, a methyl group and an ethyl group are more preferable, and a methyl group is particularly preferable.

In the substituent Z ¹ , examples of the alkylsulfinyl group include methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl, And a hexylsulfinyl group. Among them, an alkylsulfinyl group having 1 to 4 carbon atoms is preferable, an alkylsulfinyl group having 1 to 2 carbon atoms is more preferable, and a methylsulfinyl group is particularly preferable.

In the substituent Z ¹ , examples of the alkylsulfonyl group include methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, And a hexylsulfonyl group. Among them, an alkylsulfonyl group having 1 to 4 carbon atoms is preferable, an alkylsulfonyl group having 1 to 2 carbon atoms is more preferable, and a methylsulfonyl group is particularly preferable.

Of the substituent Z ¹ , examples of the fluoroalkyl group include a fluoromethyl group, a trifluoromethyl group, a fluoroethyl group, a pentafluoroethyl group, a heptafluoropropyl group, and a nonafluorobutyl group. Of these, a fluoroalkyl group having 1 to 4 carbon atoms is preferable, a fluoroalkyl group having 1 to 2 carbon atoms is more preferable, and a trifluoromethyl group is particularly preferable.

Of the substituents Z ¹ , examples of the alkoxy group include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, . Among them, an alkoxy group having 1 to 4 carbon atoms is preferable, an alkoxy group having 1 to 2 carbon atoms is more preferable, and a methoxy group is particularly preferable.

Examples of the alkylsulfanyl group in the substituent Z ¹ include methylsulfanyl, ethylsulfanyl, propylsulfanyl, isopropylsulfanyl, butylsulfanyl, isobutylsulfanyl, sec-butylsulfanyl, tert- And a hexylsulfanyl group. Among them, an alkylsulfanyl group having 1 to 4 carbon atoms is preferable, an alkylsulfanyl group having 1 to 2 carbon atoms is more preferable, and a methylsulfanyl group is particularly preferable.

Examples of the N-alkylamino group in the substituent Z ¹ include N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-sec- -butylamino group, -tert-butylamino group, N-pentylamino group and N-hexylamino group. Of these, an N-alkylamino group having 1 to 4 carbon atoms is preferable, an N-alkylamino group having 1 to 2 carbon atoms is more preferable, and an N-methylamino group is particularly preferable.

Examples of the N, N-dialkylamino group in the substituent Z ¹ include N, N-dimethylamino group, N-methyl-N-ethylamino group, N, N-diethylamino group, Isopropylamino group, N, N-dibutylamino group, N, N-diisobutylamino group, N, N-dipentylamino group and N, N-dihexylamino group. Among them, an N, N-dialkylamino group having 2 to 8 carbon atoms is preferable, an N, N-dialkylamino group having 2 to 4 carbon atoms is more preferable, and an N, N-dimethylamino group is particularly preferable.

Examples of the N-alkylsulfamoyl group in the substituent Z ¹ include N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N- An isobutylsulfamoyl group, an N-sec-butylsulfamoyl group, an N-tert-butylsulfamoyl group, an N-pentylsulfamoyl group and an N-hexylsulfamoyl group. Among them, an N-alkylsulfamoyl group having 1 to 4 carbon atoms is preferable, an N-alkylsulfamoyl group having 1 to 2 carbon atoms is more preferable, and an N-methylsulfamoyl group is particularly preferable.

Examples of the N, N-dialkylsulfamoyl group in the substituent Z ¹ include an N, N-dimethylsulfamoyl group, an N-methyl-N-ethylsulfamoyl group, an N, Diisopropylsulfamoyl group, N, N-diisopropylsulfamoyl group, N, N-diphenylsulfamoyl group, N, N-diisopropylsulfamoyl group, -Hexylsulfamoyl group, and the like. Of these, N, N-dialkylsulfamoyl groups having 2 to 8 carbon atoms are preferable, N, N-dialkylsulfamoyl groups having 2 to 4 carbon atoms are more preferable, and N, N-dimethylsulfamoyl group is particularly preferable Do.

Among them, the substituent Z ¹ is preferably a halogen atom, an alkyl group having ¹ to 2 carbon atoms, a cyano group, a nitro group, an alkylsulfonyl group having 1 to 2 carbon atoms, a fluoroalkyl group having 1 to 2 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, An N, N-dialkylamino group having 2 to 4 carbon atoms, and an alkylsulfamoyl group having 1 to 2 carbon atoms are preferable, and a halogen atom, A nitro group, a sulfo group, a carboxyl group, a trifluoromethyl group, a methoxy group, a methylsulfanyl group, an N, N-dimethylamino group and an N-methylamino group are particularly preferable.

When Y ¹ is a monocyclic aromatic hydrocarbon group which may have a substituent or a monocyclic aromatic heterocyclic group which may have a substituent, suitable examples thereof include groups represented by formulas (Y-1) to (Y-6) .

[In the formulas (Y-1) to (Y-6)

* Represents a bonding number, and Z ¹ represents the substituent Z ¹ .

a1 is an integer of 0 to 5, a2 is an integer of 0 to 4, b1 is an integer of 0 to 3, and b2 is an integer of 0 to 2, respectively. R ⁸ represents a hydrogen atom or a methyl group.

On the other hand, when a1, a2, b1 and b2 are integers of 2 or more, a plurality of Z ¹ present in the same group may be the same or different.

Y ¹ is particularly preferred from the standpoint of ease of production of compound (A) and cost, as long as Y ¹ is a group represented by formula (Y-1) or formula (Y-3).

When Y ¹ is a polycyclic aromatic hydrocarbon group which may have a substituent or a polycyclic aromatic heterocyclic group which may have a substituent, suitable examples thereof include those represented by the formulas (Y ¹ -1) to (Y ¹ -7) .

[In the formulas (Y ¹ -1) to (Y ¹ -7)

* Represents a bonding number, and Z ¹ represents the substituent Z ¹ .

V ¹ and V ² each independently represent -CO-, -S-, -NR ⁹ -, -O-, -Se- or -SO ₂ -. R ⁹ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

W ^{1 to} W ⁵ each independently represent -CH = or -N =.

Provided that at least one of V ¹ , V ² and W ^{1 to} W ⁵ represents a heteroatom such as S, N, O or Se or a group containing this heteroatom.

a represents an integer of 0 to 3;

and b represents an integer of 0 to 2.

On the other hand, when a and b are integers of 2 or more, a plurality of Z ¹ present in the same group may be the same or different.]

V ¹ and V ² are each independently -S-, -NR ⁹ - or -O-, and W ^{1 to} W ⁵ are each independently -CH = or -N =.

a is preferably 0 or 1, and b is preferably 0.

When Y ¹ is a polycyclic aromatic hydrocarbon group which may have a substituent or a polycyclic aromatic heterocyclic group which may have a substituent, it is preferable that the group represented by the formula (Y ² -1) to (Y ² -6) Is more preferable.

[In the formulas (Y ² -1) to (Y ² -6)

*, Z ¹ , a, b, V ¹ , V ² and W ¹ have the same meanings as above.

In the groups represented by formulas (Y ² -1) to (Y ² -6), Z ^{1 is preferably a} halogen atom, a methyl group, an ethyl group, an isopropyl group, a sec-butyl group, a cyano group, A nitro group, a nitro group, a carboxy group, a trifluoromethyl group, a methoxy group, a methylsulfanyl group, an N, N-dimethylamino group and an N-methylamino group are preferable and a halogen atom, a methyl group, an ethyl group, an isopropyl group, , A nitro group and a trifluoromethyl group are more preferable, and a methyl group, an ethyl group, an isopropyl group, a sec-butyl group, a pentyl group and a hexyl group are particularly preferable.

Examples of the aliphatic hydrocarbon group represented by Q ³ and Q ⁴ include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, Methylhexyl group, an octyl group, a 1-methylheptyl group, a nonyl group, a 1-methylpropyl group, a 1-methylpropyl group, a 1-methylpropyl group, a 1-methylpentyl group, An octyl group, an undecyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group and an eicosyl group. An alkyl group having 1 to 12 carbon atoms is preferable, and a methyl group and an ethyl group are particularly preferable.

Examples of the alicyclic hydrocarbon group represented by Q ³ and Q ⁴ include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group and a cyclodecyl group, A cyclic alkyl group having 3 to 12 carbon atoms is preferable.

Examples of the aromatic hydrocarbon group represented by Q ³ and Q ⁴ include phenyl, biphenyl, 1-naphthyl, 2-naphthyl, 1-fluorenyl, An aromatic hydrocarbon group having 6 to 14 carbon atoms is preferable.

The aliphatic hydrocarbon group, alicyclic hydrocarbon group and aromatic hydrocarbon group represented by Q ³ and Q ⁴ may each have a substituent. Examples of the substituent include those exemplified as Z &^lt; ¹ &gt;.

R ² and R ³ are each an alkyl group having 1 to 6 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group and an ethyl group, and particularly preferably a methyl group.

Q ³ and Q ⁴ may be bonded to each other to form an aromatic ring or aromatic heterocycle. The ring formed by Q ³ and Q ⁴ is preferably an aromatic heterocycle. For example, the formula (Q ') in the compound (A)

Is more preferably a structure represented by the formula (Q).

[In the formula (Q)

X ² is the same as the atom or group exemplified as X ¹ in formula (A), and Y ² is the same as the group exemplified as Y ¹ in formula (A).

Specific examples of the combination of X ¹ , Y ¹ , Q ³ and Q ⁴ are represented by the formula (ar) in the compound (A)

(Ar-1) to (ar-135) shown below in terms of the partial structures represented by the following formulas

Among the partial structures represented by the formula (ar), the compound (A) containing the structure represented by the formula (ar-86) is more preferable because the compound (A) The wavelength dispersion of the retardation of the optical film formed from the composition is easy to control.

D ¹ and D ² in formula (A) are each independently -OC (═O) -, -OC (═S) -, -O-CR ⁴ R ⁵ -, -NR ⁴ -CR ⁵ R ⁶ - -NR ⁴ -CO-, more preferably * -OC (= O) -, -OC (= S) -, -O-CR ⁴ R ⁵ -, -NR ⁴ -CR ⁵ R ⁶ - or * -NR ⁴ -CO-, and more preferably from * -OC (= O) -, * -OC (= S) - or * -NR ⁴ -CO - (* is represented by the formula (ar) Represents the number of bonds of Q ¹ and Q ² with the bonded benzene ring in the partial structure).

R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom, a methyl group or an ethyl group.

Examples of the divalent alicyclic hydrocarbon group represented by G ¹ and G ² include a monocyclic hydrocarbon group and a bridged cyclic hydrocarbon group, preferably a 5-membered ring or a 6-membered ring. The alicyclic hydrocarbon group may be saturated or unsaturated, but a saturated alicyclic hydrocarbon group is preferred. When the -CH ₂ - constituting the alicyclic hydrocarbon group represented by G ¹ and G ² is substituted with -O-, -S- or -NH-, or when the methine group constituting the alicyclic hydrocarbon group is replaced with a tertiary nitrogen atom . That is, G ¹ and G ² may be groups containing a hetero atom. Specific examples of G ¹ and G ² are represented by formulas (g-1) to (g-10), respectively.

The hydrogen atom contained in the divalent alicyclic hydrocarbon group represented by G ¹ and G ² may be substituted with a substituent (hereinafter, occasionally referred to as "substituent Z ² "). Examples of the substituent Z ² include an alkyl group having 1 to 4 carbon atoms such as a methyl group, an ethyl group, an isopropyl group and a tert-butyl group; An alkoxy group having 1 to 4 carbon atoms such as methoxy group and ethoxy group; A fluoroalkyl group having 1 to 4 carbon atoms such as a trifluoromethyl group; A fluoroalkoxy group having 1 to 4 carbon atoms such as a trifluoromethoxy group; Cyano; A nitro group; A halogen atom such as a fluorine atom, a chlorine atom and a bromine atom.

G ¹ and G ² are preferably bivalent alicyclic hydrocarbon groups represented by the formula (g-1). Among them, G ¹ and G ² together are more preferably a cyclohexane-1,4-diyl group, and particularly preferably a trans-cyclohexane-1,4-diyl group.

L ¹ and L ² in formula (A) are each independently a monovalent organic group, and at least one of L ¹ and L ² is an organic group having a polymerizable group.

More preferably, L ¹ is a group represented by formula (A1) (hereinafter occasionally referred to as "group (A1)"), L ² is a group represented by formula (A2) Quot; A2 &quot;).

P ¹ -F ¹ - (B ¹ -A ¹ ) _k -E ¹ - (A1)

P ² -F ² - (B ² -A ² ) ₁ -E ² - (A2)

[In the formulas (A1) and (A2)

B ¹ , B ² , E ¹ and E ² are each independently -CR ⁴ R ⁵ -, -CH ₂ -CH ₂ -, -O-, -S-, -CO-O-, -O-CO-O -, -CS-O-, -O-CS-O-, -CO-NR ¹ -, -O-CH ₂ -, -S-CH ₂ - or a single bond.

A ¹ and A ² each independently represent a divalent alicyclic hydrocarbon group having 5 to 8 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms and the methylene group constituting the alicyclic hydrocarbon group is an oxygen atom, -, and the methine group constituting the alicyclic hydrocarbon group may be substituted with a tertiary nitrogen atom.

k and l each independently represent an integer of 0 to 3; When k is an integer of 2 or more, plural B ^{1 s} may be the same or different, and plural A ^{1 s} may be the same or different. When l is an integer of 2 or more, the plurality of B ² may be the same or different, and the plurality of A ² may be the same or different.

F ¹ and F ² represent a divalent aliphatic hydrocarbon group having 1 to 12 carbon atoms.

P ¹ represents a polymerizable group.

P ² represents a hydrogen atom or a polymerizable group.

R ⁴ and R ⁵ have the same meanings as above.]

Specific examples of the divalent alicyclic hydrocarbon groups represented by A ¹ and A ² in the groups (A1) and (A2) include those exemplified as the divalent alicyclic hydrocarbon groups of G ¹ and G ² , equal suitable examples of G ¹ and G ^2. The divalent aromatic hydrocarbon groups represented by A ¹ and A ² may be monocyclic or polycyclic (including polycyclic and condensed polycyclic groups in which a plurality of aromatic rings are connected by a single bond). Examples of the divalent aromatic hydrocarbon group represented by A ¹ and A ² include those represented by formulas (a-1) to (a-8), respectively. The aromatic hydrocarbon group represented by A ¹ and A ² is preferably a group having a symmetry axis or a symmetry plane.

The hydrogen atom contained in the alicyclic hydrocarbon group and the aromatic hydrocarbon group represented by A ¹ and A ² may be substituted with a substituent. As the substituent, those exemplified as the substituent Z ² which may optionally have an alicyclic hydrocarbon group represented by G ¹ and G ² may be mentioned.

A ¹ and A ² each independently represent a 1,4-phenylene group or a cyclohexane-1,4-diyl group, and 1,4-phenylene group is preferable in that the preparation of the compound (A) desirable.

Since B ¹ and B ² tend to facilitate the preparation of the compound (A), they are preferably the same type. In addition, k, if l is 2 or more integer, B ² between the two B ¹ A, 2 A ^2, between ¹ is _{-CH 2 -CH 2 -, -C (} = O) -O-, - CO-NH-, -O-CH ₂ - or a single bond, the compound (A) tends to be more easily produced. It is preferable that B ¹ between two A ¹ and B ² between two A ² are taken together with -C (= O) -O- because it is easy to form the present optical film showing high liquid crystallinity.

B ¹ bonded to F ¹ and B ² bonded to F ² are each independently -O-, -C (= O) -O-, -OC (= O) -, -OC O-, -CO-NH-, -NH-CO- or a single bond.

k and l each independently represent an integer of 0 to 3, and k and l are more preferably 0 to 2. The sum of k and l is more preferably 4 or less. When k and l are in the above ranges, the compound (A) tends to show more liquid crystallinity.

Each of F ¹ and F ² is independently an alkanediyl group having 1 to 12 carbon atoms, more preferably a straight-chain alkanediyl group. Particularly, an unsubstituted alkanediyl group is preferable. The hydrogen atom contained in the alkanediyl group may be substituted with an alkoxy group having 1 to 5 carbon atoms or a halogen atom. The -CH ₂ - constituting the alkanediyl group may be substituted with -O- or -C (= O) -.

P ¹ and P ² are each a hydrogen atom or a polymerizable group, and at least one of them is a polymerizable group. When it is desired to obtain the present optical film having better hardness, it is preferable that P ¹ and P ² together are a polymerizable group.

The polymerizable group means a characteristic group capable of polymerizing the compound (A), and specific examples thereof include a vinyl group, a vinyloxy group, a styryl group, a p- (2-phenylethenyl) phenyl group, an acryloyl group, a methacryloyl group , A polymerizable group having an ethylenic unsaturated group such as an acryloyloxy group and a methacryloyloxy group; A carboxy group; An acetyl group; A hydroxy group; Carbamoyl group; An alkylamino group having 1 to 4 carbon atoms; An amino group; An oxiranyl group; An oxetanyl group, a formyl group, an isocyanato group or an isothiocyanato group.

As the polymerizable group, a radical polymerizable group and a cationic polymerizable group suitable for photopolymerization of the compound (A) are preferable, and acryloyl group, methacryloyl group, acryloyloxy group and methacryloyloxy group are particularly preferable. Among them, the polymerizable group is preferably independently an acryloyloxy group or a methacryloyloxy group, particularly preferably an acryloyloxy group.

In consideration of easiness of production of the compound (A), it is preferable that the group (A1) and the group (A2) are the same, that is, L ¹ and L ² are the same.

Similarly, in the compound (A), D ¹ and D ² are the same and G ¹ and G ² are the same. That is, in the compound (A), a group represented by -D ¹ -G ¹ -L ¹ and a group represented by -D ² -G ² -L ² are the same. In this case, the compound (A) can be more easily produced.

Specific examples of -D ¹ -G ¹ -L ¹ when L ¹ is a group represented by formula (A1) and specific examples of -D ² -G ² -L ² when L ² is a group represented by formula (A2) Examples thereof include groups represented by the following formulas (R-1) to (R-134), and the like.

On the other hand, n in the formulas (R-1) to (R-134) represents an integer of 2 to 12, preferably 3 to 10, and more preferably 4 to 8.

It is preferable that the compound (A) wherein L ¹ is the group (A1) and L ² is the group (A2) also satisfy the relations of the formulas (1) and (2).

(N _? -4) / 3 <k + 1 + 4 (1)

12 _? N _? 22 (2)

[In the formulas (1) and (2), N _π is included in the aromatic ring of the moiety excluding -D ¹ -G ¹ -L ¹ and -D ² -G ² -L ² in the formula (A) The number of electrons to be excited. k and l are as defined above.

Examples of the compound (A) include the following compounds (i) to (xxvii). In the table, L ¹ represents -D ¹ -G ¹ -L ¹ , and L ² represents -D ² -G ² -L ² .

In the table, for example, the compound (A) represented by (i) (hereinafter referred to as "compound (xvi)" according to the numbers in the tables) has a partial structure represented by formula (ar) and the structure represented by formula ^{(ar-39), -D 1} -G 1 -L group is represented by ^{1 (R-1) ~ (} R-48), (R-56) ~ (R-120) and ( R-129 to R-131, and groups represented by -D ² -G ² -L ² are groups selected from the group consisting of (R-1) to (R-48) (R-131).

For example, the compound (xvi) has a structure in which the partial structure represented by the formula (ar) is represented by the formula (ar-39), the group represented by -D ¹ -G ¹ -L ¹ is (R-129) to (R-131), and the group represented by -D ² -G ² -L ² is a group selected from the group consisting of R-1) ~ (R- 48) and (R-56) ~ (a structure represented by R-131) resulting compound with the formula (ar-40) is selected from the group consisting of, -D ¹ -G ¹ A group represented by -L ¹ is a group selected from the group consisting of (R-1) to (R-48), (R-56) to , A group represented by -D ² -G ² -L ² and a group selected from the group consisting of (R-1) to (R-48) and (R-56) to (R-131) Compound (xvi) means a mixture of two compounds (A).

Specific examples of the compounds (A) listed in the table include the following compounds. The compound (i), the compound (iii), the compound (iv), the compound (v), the compound (viii), the compound (ix), the compound (x), the compound (xvii), compound (xix), compound (xx), compound (xxii), compound (xxiii), compound (xxiv) and compound (xxv). The following formulas are intended to include all stereoisomers. Also, it is preferable that the compounds (i) to (xxv) are all trans-cyclohexane-1,4-diyl group as the cyclohexane-1,4-diyl group.

As the compound (A), there may be mentioned those represented by the formulas (A1) to (A61), respectively.

(Two * in formula (A1) are combined with any of (A1-1) to (A1-8) *)

(Two a * in formula (A2) are combined with any of (A2-1) to (A2-8) *)

(Two * in formula (A3) are combined with any of (A3-1) to (A3-8)).

(The two * in formula (A4) are combined with any of (A4-1) to (A4-8)

(The two * in formula (A5) are combined with any of (A5-1) to (A5-8)).

(The two * in formula (A6) are combined with any of (A6-1) to (A6-8)

(Two * in formula (A7) are combined with any of (A7-1) to (A7-8)

(The two * in formula (A8) are combined with any of (A8-1) to (A8-8)

(The two * in formula (A9) are combined with any of (A9-1) to (A9-8)

(The two * in formula (A10) are combined with any of (A10-1) to (A10-8)

(The two * in formula (A11) are combined with any of (A11-1) to (A11-8)).

(The two * in formula (A12) are combined with any of (A12-1) to (A12-8)

(Two * in formula (A13) are combined with any of (A13-1) to (A13-8)

(Two * in formula (A14) are combined with any of (A14-1) to (A14-8)

(The two * in formula (A15) are combined with any of (A15-1) to (A15-8)

(The two * in formula (A16) are combined with any of (A16-1) to (A16-8)).

(The two * in formula (A17) are combined with any of (A17-1) to (A17-8)

(The two * in formula (A18) are combined with any of (A18-1) to (A18-8)

(The two * in formula (A19) are combined with any of (A19-1) to (A19-8)

(The two * in formula (A20) are combined with any of (A20-1) to (A20-8)).

(The two * in formula (A21) are combined with any of (A21-1) to (A21-8)).

(The two * in formula (A22) are combined with any of (A22-1) to (A22-8)).

(Two * in formula (A23) are combined with any of (A23-1) to (A23-8)

(The two * in formula (A24) are combined with any of (A24-1) to (A24-8)

(The two * in formula (A25) are combined with any of (A25-1) to (A25-8)

(The two * in formula (A26) are combined with any of (A26-1) to (A26-8)).

(The two * in formula (A27) are combined with any of (A27-1) to (A27-8)

(The two * in formula (A28) are combined with any of (A28-1) to (A28-8)

(The two * in formula (A29) are combined with any of (A29-1) to (A29-8)

(The two * in formula (A30) are combined with any of (A30-1) to (A30-8)

(The two * in formula (A31) are combined with any of (A31-1) to (A31-8)

(The two * in formula (A32) are combined with any of (A32-1) to (A32-8)).

(The two * in formula (A33) are combined with any of (A33-1) to (A33-8)

(The two * in formula (A34) are combined with any of (A34-1) to (A34-8)

(The two * in formula (A35) are combined with any of (A35-1) to (A35-8)

(The two * in formula (A36) are combined with any of (A36-1) to (A36-8)

(The two * in formula (A37) are combined with any of (A37-1) to (A37-8)

(The two * in formula (A38) are combined with any of (A38-1) to (A38-8)

(The two * in formula (A39) are combined with any of (A39-1) to (A39-8)

(The two * in formula (A40) are combined with any of (A40-1) to (A40-8)).

(The two * in formula (A41) are combined with any of (A41-1) to (A41-8)).

(The two * in formula (A42) are combined with any of (A42-1) to (A42-8)

(The two * in formula (A43) are combined with any of (A43-1) to (A43-8)

(The two * in formula (A44) are combined with any of (A44-1) to (A44-8)

(Two * in formula (A45) are combined with any of (A45-1) to (A45-8)

(The two * in formula (A46) are combined with any of (A46-1) to (A46-8)).

(The two * in formula (A47) are combined with any of (A47-1) to (A47-8)

(The two * in formula (A48) are combined with any of (A48-1) to (A48-8)

(The two * in formula (A49) are combined with any of (A49-1) to (A49-8)

(The two * in formula (A50) are combined with any of (A50-1) to (A50-8)).

(The two * in formula (A51) are combined with any of (A51-1) to (A51-8)).

(The two * in formula (A52) are combined with any of (A52-1) to (A52-8)).

(The two * in formula (A53) are combined with any of (A53-1) to (A53-8)

(The two * in formula (A54) are combined with any of (A54-1) to (A54-8)

(Two * in formula (A55) are combined with any of (A55-1) to (A55-8)

(The two * in formula (A56) are combined with any of (A56-1) to (A56-8)

(The two * in formula (A57) are combined with any of (A57-1) to (A57-8)

(The two * in formula (A58) are combined with any of (A58-1) to (A58-8)

(The two * in formula (A59) are combined with any of (A59-1) to (A59-8)

(The two * in formula (A60) are combined with any of (A60-1) to (A60-8)).

(The two * in formula (A61) are combined with any of (A61-1) to (A61-8)).

As the compound (A), the following may also be used.

The compound (A) can be synthesized by a condensation reaction, an esterification reaction, a Williamson reaction, a uremain reaction, a biotissue reaction, a Schiff base formation reaction or the like which are described in Methoden der Organischen Chemie, Organic Reactions, Organic Syntheses, Comprehensive Organic Synthesis, , Benzylation reaction, Sonogashira reaction, Suzuki-Miyaura reaction, Negishi reaction, Cumarane reaction, Hiyama reaction, Buchwald-Hartwig reaction, Friedel-Crafts reaction, Heck reaction and aldol reaction Can be manufactured.

(A) in which D ¹ and D ² are * -O-CO- is taken as an example, and a production method thereof will be briefly described. First, compounds (1-1) and compounds (1-2) represented by the formula (1-1) and compounds (1-2) Compound (1-2) is reacted to obtain a compound represented by formula (1-3) (compound (1-3)).

Wherein X ¹ , Y ¹ , Q ¹ and Q ² have the same meanings as in formula (A).

Wherein G ¹ , E ¹ , A ¹ , B ¹ , F ¹ , P ¹ and k have the same meanings as above.

In the formula, X ¹ , Y ¹ , Q ¹ , Q ² , G ¹ , E ¹ , A ¹ , B ¹ , F ¹ , P ¹ and k have the same meanings as above.

The compound (A) can be prepared by reacting the obtained compound (1-3) with the compound (compound (1-4)) represented by the formula (1-4).

Wherein G ² , E ² , A ² , B ² , F ² , P ² and l have the same meanings as above.

The reaction between the compound (1-1) and the compound (1-2) and the reaction between the compound (1-3) and the compound (1-4) are preferably carried out in the presence of an esterifying agent.

Examples of the esterifying agent (condensing agent) include 1-cyclohexyl-3- (2-morpholinoethyl) carbodiimide-para-toluenesulfonate, dicyclohexylcarbodiimide, 1- Aminopropyl) carbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (some water-soluble carbodiimide: commercially available as Water Soluble Carbodiimide), bis (2,6-diisopropylphenyl ) Carbodiimides such as carbodiimide, bis (trimethylsilyl) carbodiimide and bisisopropylcarbodiimide; 2-methyl-6-nitrobenzoic anhydride, 2,2'-carbonylbis-1H-imidazole, 1,1'-oxalyldiimidazole, diphenylphosphoryl azide, 1- Benzyltriazole-1-yloxythiophene hexafluorophosphate, 1H-benzotriazol-1-yloxytris (dimethylamino) phosphine N, N ', N'-tetramethyl-O- (N-succinimidyl) uronium tetrafluoroborate, N- (1,2,2,2-tetrachloroethoxy Carbonyloxy) succinimide, N-carbobenzoxysuccinimide, O- (6-chlorobenzotriazol-1-yl) -N, N, N ', N'-tetramethyluronium tetrafluoro Borate, O- (6-chlorobenzotriazol-1-yl) -N, N, N ', N'-tetramethyluronium hexafluorophosphate, 2-bromo-1-ethylpyridinium tetrafluoroborate , 2-chloro-1,3-dimethylimidazolinium chloride, 2-chloro-1,3-dimethylimidazolinium 2-chloro-1-methylpyridinium iodide, 2-chloro-1-methylpyridinium para-toluenesulfonate, 2-fluoro-1-methylpyridinium para- toluenesulfonate, trichloro Rosacetan pentachlorophenyl ester, and the like. Among them, dicyclohexylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, 1-ethyl-3- (3 (Dimethylaminopropyl) carbodiimide hydrochloride, bis (2,6-diisopropylphenyl) carbodiimide, bis (trimethylsilyl) carbodiimide, bisisopropyl carbodiimide, 2,2'- 1H-imidazole is preferred.

When the composition (1) contains the compound (A) as the polymerizable liquid crystal compound, its content is preferably from 10 to 99.9% by mass, more preferably from 20 to 99% by mass, , More preferably from 50 to 97 mass%, and even more preferably from 80 to 95 mass%. When the content of the compound (A) is in the above range, the obtained optical film (1) can be subjected to the same polarization conversion in a wide wavelength region. The solid content refers to the total amount of components excluding the low volatility component such as a solvent in the present composition (1). In the composition (1), the compound (A) may be used alone or two or more kinds of the compounds (A) may be used in combination as shown in the table (xvi).

Examples of the polymerizable liquid crystal compound include "3.8.6 network (full crosslinking type)" and "6.5.1 liquid crystal material b." In the liquid crystal manual (edited by LCD Manual Editing Committee, Maruzen Co., Polymerizable nematic liquid crystal material ", a compound having a polymerizable group, the compounds disclosed in JP-A-2010-31223, JP-A-2010-270108, JP-A-2011-6360 and JP- And a polymerizable liquid crystal compound described in JP-A-2001-346991.

As the polymerizable liquid crystal compound, for example, a compound represented by formula (3) (hereinafter referred to as &quot; compound (3) &quot;

P ¹¹ -E ¹¹ - (B ¹¹ -A ¹¹ ) _t -B ¹² -G (3)

[In the formula (3)

A ¹¹ represents an aromatic heterocycle which may have a substituent, an aromatic hydrocarbon group which may have a substituent, or an alicyclic hydrocarbon group which may have a substituent.

B ¹¹ and B ¹² each independently represent -C≡C-, -CH═CH-, -CH ₂ -CH ₂ -, -O-, -S-, -CO-, -CO-O-, -CS- , -O-CO-O-, -CR 13 R 14 -, -CR 13 R 14 -CR 15 R 16 -, -O-CR 13 R 14 -, -CR 13 R 14 -O-CR 15 R 16 - , -CO-O-CR ¹³ R ¹⁴ -, -O-CO-CR ¹³ R ¹⁴ -, -CR ¹³ R ¹⁴ -O-CO-CR ¹⁵ R ¹⁶ -, -CR ¹³ R ¹⁴ -CO- ^{15 R 16 -, -NR 13 -CR} 14 R 15 -, -CH = N-, -N = N-, -CO-NR 16 -, -OCH 2 -, -OCF 2 -, -CH 2 O-, -CF ₂ O-, -CH = CH-CO-O-, or a single bond. R ¹³ to R ^{16 each} represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

G represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 13 carbon atoms, an alkoxy group having 1 to 13 carbon atoms, a fluoroalkyl group having 1 to 13 carbon atoms, an N-alkylamino group having 1 to 13 carbon atoms, a cyano group, ¹² -P ¹² .

E ¹¹ and E ^{12 each} represent an alkanediyl group having 1 to 18 carbon atoms, the hydrogen atom contained in the alkanediyl group may be substituted with a halogen atom, and the methylene group contained in the alkanediyl group may be replaced with an oxygen atom or -CO- And may be substituted.

P ¹¹ and P ¹² represent a polymerizable group.

t represents an integer of 1 to 5; When t is an integer of 2 or more, a plurality of B ^{11 s} may be the same or different, and a plurality of A ^{11 s} may be the same or different.

Examples of the aromatic hydrocarbon ring represented by A ¹¹ include a benzene ring, a naphthalene ring, an anthracene ring and a phenanthroline ring. Examples of the aromatic heterocycle include a furan ring, a pyrrole ring, a thiophene ring, a pyridine ring, a thiazole ring and a benzothiazole ring And the like. Among them, benzene ring, thiazole ring and benzothiazole ring are preferable. Examples of the aromatic hydrocarbon ring or aromatic heterocycle represented by A ¹¹ include bivalent groups represented by formulas (Ara-1) to (Ara-11), respectively.

[In the formulas (Ara-1) to (Ara-11)

X ³ represents the same meaning as X ³ in the formula (A). A plurality of X ¹ existing in the same group may be the same or different.

Y ³ is the same as the group exemplified as Y ¹ in formula (A).

Z ³ represents the same group as that exemplified as Z ¹ in formula (A).

W ^a and W ^b each independently represent a hydrogen atom, a cyano group, a methyl group or a halogen atom.

m represents an integer of 0 to 6;

n represents an integer of 0 to 4;

and o represents an integer of 0 to 2.

When m, n and o are an integer of 2 or more, a plurality of Z ³ present in the same group may be the same or different.]

As the aromatic hydrocarbon ring or aromatic heterocycle represented by A ¹¹ , groups represented by formulas (Ara-1) and (Ara-7) are preferred, and specific examples thereof include the following groups.

The carbon number of the alicyclic hydrocarbon group represented by A ¹¹ is, for example, 3 to 18, preferably 5 to 12, and particularly preferably 5 or 6. Examples of the alicyclic hydrocarbon group represented by A ¹¹ include a cyclohexane-1,4-diyl group and the like. Examples of the substituent which the alicyclic hydrocarbon group may have include a halogen atom, an alkyl group having 1 to 6 carbon atoms which may have a fluoro group, an alkoxy group having 1 to 6 carbon atoms, which may have a fluoro group, a nitro group and a cyano group.

Examples of the polymerizable group represented by P ¹¹ and P ¹² include groups exemplified as the polymerizable group represented by P ¹ and P ² of the compound (A). (3) can be easily produced. Therefore, it is preferable to use a compound having a structure of P &lt; ¹¹ &gt; and P &lt; ¹¹ &gt; And the polymerizable group represented by P ¹² are preferably groups represented by formulas (P-1) to (P-5), respectively.

[In the formulas (P-1) to (P-5)

R ¹⁷ to R ²¹ each independently represent an alkyl group having 1 to 6 carbon atoms or a hydrogen atom. * Represents the number of bonds with B ^11. ]

E ¹¹ and E ¹² are alkanediyl groups having 1 to 18 carbon atoms, and alkanediyl groups having 1 to ¹² carbon atoms, which are linear or have one branching point, are preferable.

Examples of the compound (3) include the following compounds.

When the composition (1) contains the compound (3) and / or the compound (A) as the polymerizable liquid crystal compound, ) Is 90 parts by mass or less, preferably 70 parts by mass or less, and more preferably 40 parts by mass or less. On the other hand, for example, by adjusting the content of the structural unit derived from the compound (A) and the content of the structural unit derived from the compound (3), the present optical film (1) having desired wavelength dispersion characteristics can be formed. The optical film (1) tends to exhibit further reverse wavelength dispersion characteristics when the content of the structural unit derived from the compound (A) is increased. In order to form the present optical film (1) having desired wavelength dispersion characteristics, it is preferable to prepare about 2 to 5 kinds of the present composition (1) having different content of the structural unit derived from the compound (A) ), An optical film having the same film thickness is prepared and its phase difference value is obtained. From the result, the correlation between the content of the structural unit derived from the compound (A) and the retardation value of the optical film was determined, and from the obtained correlation, the compound required for imparting a desired retardation value to the optical film in the film thickness The content of the structural unit derived from the structural unit A may be determined.

As the polymerizable liquid crystal compound, for example, a compound containing a group represented by the formula (X1) (hereinafter referred to as &quot; compound (X1) &quot;

P ¹¹ -B ¹¹ -E ¹¹ -B ¹² -A ¹¹ -B ¹³ - * (X1)

(In the formula (X1), P ¹¹ represents a polymerizable group.

A ¹¹ represents a divalent alicyclic hydrocarbon group or a divalent aromatic hydrocarbon group. The hydrogen atom contained in the divalent alicyclic hydrocarbon group and the divalent aromatic hydrocarbon group may be substituted with a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group or a nitro group, And the hydrogen atom contained in the above-mentioned C 1-6 alkoxy group may be substituted with a fluorine atom.

B ¹¹ is -O-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -CO-NR ¹⁶ -, -NR ¹⁶ -CO-, CS- or a single bond. R ¹⁶ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

B ¹² and B ¹³ are each independently selected from the group consisting of -C≡C-, -CH═CH-, -CH ₂ -CH ₂ -, -O-, -S-, -C (═O) -, -C ) -O-, -OC (= O) -, -OC (= O) -O-, -CH = N-, -N = CH-, -N = N-, -C (= O) -NR 16 -, -NR ¹⁶ -C (= O) -, -OCH ₂ -, -OCF ₂ -, -CH ₂ O-, -CF ₂ O-, -CH = CH-C OC (= O) -CH = CH- or a single bond.

E ¹¹ represents an alkanediyl group having 1 to 12 carbon atoms, the hydrogen atom contained in the alkanediyl group may be substituted with an alkoxy group having 1 to 5 carbon atoms, and the hydrogen atom contained in the alkoxy group may be substituted with a halogen atom . The -CH ₂ - constituting the alkanediyl group may be substituted with -O- or -CO-.

* Represents the number of bonds)

The number of carbon atoms of the aromatic hydrocarbon group and the alicyclic hydrocarbon group of A ¹¹ is, for example, 3 to 18, preferably 5 to 12, and particularly preferably 5 or 6. A ¹¹ is preferably a cyclohexane-1,4-diyl group or a 1,4-phenylene group.

E ¹¹ is preferably a straight chain alkynyl group having 1 to 12 carbon atoms. The -CH ₂ - constituting the alkanediyl group may be substituted with -O-.

Specific examples include methylene, ethylene, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane- Di-n-octyl, 1,7-diyl, octane-1,8-diyl, nonane-1,9-diyl, decane-1,10-diyl, undecane-1,11-diyl and dodecane- A straight chain alkanediyl group having 1 to 12 carbon atoms such as a diaryl group; _{-CH 2 -CH 2 -O-CH 2} -CH 2 -, -CH 2 -CH 2 -O-CH 2 -CH 2 -O-CH 2 -CH 2 - and -CH ₂ -CH ₂ -O-CH the like _{- 2 -CH 2 -O-CH 2} -CH 2 -O-CH 2 -CH 2.

The polymerizable group represented by P &lt; ¹¹ &gt; is preferably a radical polymerizable group or a cationic polymerizable group in view of high polymerization reactivity, especially photopolymerization reactivity, and is easily handled. Since the production of the liquid crystal compound itself is easy, Is preferably a group represented by formulas (P-11) to (P-15).

[In the formulas (P-11) to (P-15)

And R ¹⁷ to R ²¹ each independently represent an alkyl group having 1 to 6 carbon atoms or a hydrogen atom.

More specifically, the groups represented by the formulas (P-11) to (P-15) include groups represented by the following formulas (P-16) to (P-20).

P ¹¹ is preferably a group represented by the formulas (P-14) to (P-20), more preferably a vinyl group, a p-stilbene group, an epoxy group or an oxetanyl group.

Particularly preferably, the group represented by P ¹¹ -B ¹¹ - is an acryloyloxy group or a methacryloyloxy group.

Examples of the compound (X1) include compounds represented by the following formulas (I), (II), (III), (IV), (V) or (VI)

P ¹¹ -B ¹¹ -E ¹¹ -B ¹² -A ¹¹ -B ¹³ -A ¹² -B ¹⁴ -A ¹³ -B ¹⁵ -A ¹⁴ -B ¹⁶ -E ¹² -B ¹⁷ -P ¹² (I)

P ¹¹ -B ¹¹ -E ¹¹ -B ¹² -A ¹¹ -B ¹³ -A ¹² -B ¹⁴ -A ¹³ -B ¹⁵ -A ¹⁴ -F ¹¹ (II)

P ¹¹ -B ¹¹ -E ¹¹ -B ¹² -A ¹¹ -B ¹³ -A ¹² -B ¹⁴ -A ¹³ -B ¹⁵ -E ¹² -B ¹⁷ -P ¹² (III)

P ¹¹ -B ¹¹ -E ¹¹ -B ¹² -A ¹¹ -B ¹³ -A ¹² -B ¹⁴ -A ¹³ -F ¹¹ (IV)

P ¹¹ -B ¹¹ -E ¹¹ -B ¹² -A ¹¹ -B ¹³ -A ¹² -B ¹⁴ -E ¹² -B ¹⁷ -P ¹² (V)

P ¹¹ -B ¹¹ -E ¹¹ -B ¹² -A ¹¹ -B ¹³ -A ¹² -F ¹¹ (VI)

(Wherein,

A ¹² ~ A ¹⁴ agree with A ¹¹ , B ¹⁴ ~ B ¹⁶ agree with B ¹² , B ¹⁷ agrees with B ^11, and E ¹² agrees with E ¹¹ .

F ¹¹ is an alkoxy group of a hydrogen atom, an alkyl group having a carbon number of 1 to 13, 1 to 13 carbon atoms, a cyano group, a nitro group, a trifluoromethyl group, a dimethylamino group, a hydroxy group, a methylol group, a formyl group, a sulfo group (-SO ₃ H A carboxy group, an alkoxycarbonyl group having 1 to 10 carbon atoms, or a halogen atom, and -CH ₂ - constituting the alkyl group and the alkoxy group may be substituted with -O-)

Specific examples of the compound (X1) include compounds represented by the following formulas (I-1) to (I-4), (II- , Compounds represented by formulas (IV-1) to (IV-19), formulas (V-1) to (V-2), and formulas (VI- . In the formula, k1 and k2 represent an integer of 2 to 12. These compounds are preferable because the compound itself is easily produced or commercially available.

The content of the compound (X1) in the composition (1) is represented by the content ratio with respect to the solid content of the composition (1), preferably 10 to 99.9 mass%, more preferably 20 to 99 mass% More preferably 98% by mass, and particularly preferably 80% by mass to 97% by mass. Within the above-mentioned range, the composition can be used as a composition having excellent coating property (coating property) on the substrate during production of the present optical film. The solid content refers to the total amount of components excluding the low volatile component such as a solvent in the composition (B).

1-3. Photopolymerization initiator

The photopolymerization initiator is a compound capable of generating an active radical by the action of light to start polymerization of the polymerizable liquid crystal compound. Examples of the photopolymerization initiator include alkylphenone compounds, benzoin compounds, benzophenone compounds and oxime compounds.

Examples of the alkylphenone compound include an? -Aminoalkylphenone compound,? -Hydroxyalkylphenone compound and? -Alkoxyalkylphenone compound.

Examples of the? -aminoalkylphenone compound include 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan- 1-one and 2-dimethylamino-1- (4-morpholinophenyl) -2- (4-methylphenylmethyl) butan-1-one, 1- (4-methylphenyl) propane-1-one and 2-dimethylamino-1- (4-morpholinophenyl) have. aminoalkylphenone compounds are commercially available products such as Irgacure (registered trademark) 369, 379EG, 907 (manufactured by BASF Japan) and Sheikol (registered trademark) BEE (manufactured by Seiko Chemical) It is good.

Examples of the? -hydroxyalkylphenone compound include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) Propan-1-one, 1-hydroxycyclohexyl phenyl ketone and oligomers of 2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl] propan-1-one. The? -hydroxyalkylphenone compound may be a commercially available product such as Irgacure 184, 2959, 127 (manufactured by BASF Japan Co., Ltd.) and Seikolol Z (manufactured by Seiko Kagaku Co., Ltd.).

Examples of the? -alkoxyalkylphenone compound include diethoxyacetophenone and benzyldimethylketal. The? -alkoxyalkylphenone compound may be a commercially available product such as Irgacure 651 (manufactured by BASF Japan Co., Ltd.).

As the alkylphenone compound, an? -Aminoalkylphenone compound is preferable, and a compound represented by the formula (C-1) is more preferable. By including such a compound, there is a tendency that the obtained optical film has excellent heat resistance and heat and humidity resistance.

[In the formula (C-1), Q ³ represents a hydrogen atom or a methyl group.]

Examples of the benzoin compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether and benzoin isobutyl ether.

Examples of the benzophenone compound include benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenylsulfide and 3,3 ', 4,4'-tetra (tert- Benzyl) benzophenone, 2,4,6-trimethylbenzophenone, and the like.

As the oxime compounds, N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-benzoyloxy- 1- (4-phenylsulfanylphenyl) -Imine, N-acetoxy-1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol- -6- {2-methyl-4- (3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy) benzoyl} -9H-carbazol-3-yl] ethan- . Commercially available products such as Irgacure OXE-01, OXE-02 (manufactured by BASF Japan) and N-1919 (manufactured by ADEKA) may be used as the oxime compounds.

As the photopolymerization initiator, an acetophenone compound, a benzoin compound, a benzophenone compound, an oxime compound and the like may be used singly or two or more of them may be used in combination. Among them, it is preferable to use an acetophenone compound as a photopolymerization initiator. The amount of the acetophenone compound to be used is preferably 90 parts by mass or more based on the total amount of the photopolymerization initiator, more preferably the whole photopolymerization initiator is an acetophenone compound.

The content of the photopolymerization initiator in the composition (1) is preferably 0.1% by mass to 30% by mass, and more preferably 0.5% by mass to 10% by mass, based on the solid content of the composition (1). Within the above range, disturbing the orientation of the compound (A) can be further suppressed when the polymerizable liquid crystal compound contained in the present composition (1) is polymerized. On the other hand, the solid content refers to the total amount of components excluding the low volatile component such as a solvent in the present composition (1).

1-4. Organic solvent

The composition (1) preferably contains a solvent, particularly an organic solvent, in order to improve the operability of producing an optical film. As the organic solvent, an organic solvent capable of dissolving the constituent components of the composition (1) is preferable, and furthermore, a solvent inert to the polymerization reaction of the polymerizable liquid crystal compound contained in the present composition (1) is more preferable. Specific examples thereof include alcohol solvents such as methanol, ethanol, ethylene glycol, isopropyl alcohol, propylene glycol, methyl cellosolve, butyl cellosolve, propylene glycol monomethyl ether and phenol; Ester solvents such as ethyl acetate, butyl acetate, ethylene glycol methyl ether acetate,? -Butyrolactone, propylene glycol methyl ether acetate and ethyl lactate; Ketone solvents such as acetone, methyl ethyl ketone, cyclopentanone, cyclohexanone, methyl amyl ketone and methyl isobutyl ketone; Non-chlorine based aliphatic hydrocarbon solvents such as pentane, hexane and heptane; Non-chlorinated aromatic hydrocarbon solvents such as toluene and xylene; Nitrile solvents such as acetonitrile; Ether solvents such as tetrahydrofuran and dimethoxyethane; Chlorinated solvents such as chloroform and chlorobenzene; And the like. The organic solvent may be used singly or in combination of plural kinds. Among them, alcohol solvents, ester solvents, ketone solvents, non-chlorine-based aliphatic hydrocarbon solvents and non-chlorine-based aromatic hydrocarbon solvents are preferable. Particularly, the constituent components of the present composition are excellent in compatibility and can also be dissolved in alcoholic solvents, ester solvents, ketone solvents, non-chlorine-based aliphatic hydrocarbon solvents, and chlorinated aromatic hydrocarbon solvents. Therefore, chlorinated solvents such as chloroform are used It is possible to obtain the present composition capable of producing the present optical film by coating on a suitable substrate.

When the composition (1) contains an organic solvent, its content is preferably 10 parts by mass to 10000 parts by mass, more preferably 100 parts by mass to 5,000 parts by mass, per 100 parts by mass of the solid content. The solid content concentration in the composition (1) is preferably 2% by mass to 50% by mass, and more preferably 5% by mass to 50% by mass. The solid content refers to the total amount of components excluding the low volatility component such as a solvent in the present composition (1).

The composition (1) may contain additives such as a photosensitizer, a leveling agent, a chiral agent, and a polymerization inhibitor.

1-5. Photosensitizer

Examples of the photosensitizer include xanthones such as xanthone and thioxanthone; Anthracene having a substituent such as anthracene and alkyl ether; Phenothiazine; Ruben.

By using a photosensitizer, the polymerization of a polymerizable liquid crystal compound or the like can be highly sensitized. The amount of the photosensitizer used is, for example, from 0.1 part by mass to 30 parts by mass, and preferably from 0.5 parts by mass to 10 parts by mass with respect to 100 parts by mass of the polymerizable liquid crystal compound.

1-6. Leveling agent

Examples of the leveling agent include organic modified silicone oil type, polyacrylate type, and perfluoroalkyl type leveling agent. Specifically, for example, DC3PA, SH7PA, DC11PA, SH28PA, SH29PA, SH30PA, ST80PA, ST86PA, SH8400, SH8700, FZ2123 (all above, manufactured by Oradea Corning), KP321, KP323, KP324, KP326, KP340, KP341 (All of which are manufactured by Shin-Etsu Kagaku Kogyo Kabushiki Kaisha), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, TSF4460 Fluorine (registered trademark) FC-72, FC-40, FC-43 and FC-3283 (all manufactured by Sumitomo 3M Ltd.), Megapark (registered trademark) R -08, R-30, R-90, F-410, F-411, F-443, F-445, F-470, F-477, (All manufactured by Mitsubishi Materials Denshikage Co., Ltd.), F-482 and F-483 (all manufactured by DIC Corporation), F-Top (trade name) EF301, S-381, S-382, S-383, S-393, SC-101, SC-105, KH-40, SA- BM-1100, BYK-352, BYK-353, and BYK-361N (all manufactured by Daikin Fine Chemicals Co., Ltd.), trade name E1830 and E5844 Trade name: BM Chemie). The leveling agent may be used alone, or two or more kinds thereof may be used in combination.

By using the leveling agent, the obtained optical film can be smoothened more. The crosslinking density of the optical film obtained by controlling the fluidity of the composition or polymerizing the polymerizable liquid crystal compound during the production of the optical film can be adjusted. The amount of the leveling agent to be used is, for example, from 0.1 part by mass to 30 parts by mass, preferably from 0.1 part by mass to 10 parts by mass with respect to 100 parts by mass of the polymerizable liquid crystal compound.

1-7. Chiral

As a chiral agent, a known chiral agent (for example, described in the Liquid Crystal Device Handbook, Chapter 3, Section 4-3, TN, STN Chiral Form, page 199, JSPS 142, Can be used.

Chiral agents generally include asymmetric carbon atoms, but axial asymmetric compounds or asymmetric compounds that do not contain asymmetric carbon atoms can also be used as chiral agents. Examples of condensed asymmetric compounds or planar asymmetric compounds include binaphthyl, helixene, paracyclophane, and derivatives thereof.

For example, JP-A-2007-269640, JP-A-2007-269639, JP-A-2007-176870, JP-A-2003-137887, JP-A-2000-515496, 2007-169178, and JP-A-9-506088, and paliocolor (registered trademark) LC756 manufactured by BASF Japan Co., Ltd. can be mentioned.

The amount of the chiral agent used is, for example, from 0.1 part by mass to 30 parts by mass, and preferably from 1.0 part by mass to 25 parts by mass with respect to 100 parts by mass of the polymerizable liquid crystal compound. Within the above range, it is possible to further suppress disturbing the orientation of the polymerizable liquid crystal compound when the polymerizable liquid crystal compound contained in the present composition (1) is polymerized.

1-8. Polymerization inhibitor

Examples of the polymerization inhibitor include hydroquinone having a substituent such as hydroquinone and alkyl ether; Catechol having a substituent such as an alkyl ether such as butyl catechol; Radical chelating agents such as pyrogallol, 2,2,6,6-tetramethyl-1-piperidinyloxy radical; Thiophenols,? -Naphthyl amines,? -Naphthols, and the like.

By using a polymerization inhibitor, the polymerization of the polymerizable liquid crystal compound can be controlled and the stability of the optical film (1) can be improved. The content of the polymerization inhibitor is, for example, from 0.1 part by mass to 30 parts by mass, and preferably from 0.5 part by mass to 10 parts by mass, based on 100 parts by mass of the polymerizable liquid crystal compound. Within the above range, the polymerizable liquid crystal compound can be polymerized without disturbing the orientation of the polymerizable liquid crystal compound.

2. Optical film

The present optical film (1) is obtained by polymerizing a polymerizable liquid crystal compound. The present optical film (1) is a film capable of transmitting light and having an optical function. The optical function means refraction, birefringence, and the like.

Among the present optical films (1), those having excellent transparency in the visible light region are preferable because they can be used as members for various display devices. The thickness of the optical film 1 can be appropriately adjusted depending on the use of the present optical film 1, and it is preferably 0.1 m to 10 m, more preferably 0.2 m to 5 m in view of reducing the photoelasticity Do.

When the present optical film (1) is used for a display device, the present optical film (1) may be used as a single layer, or a plurality of sheets of the present optical film (1) may be laminated to form a laminate or may be combined with other films. A viewing angle increasing film, a viewing angle increasing film, an antireflection film, a polarizing film, a circularly polarizing film, an elliptically polarizing film, and a luminance improving film by using the film in combination with another film.

In particular, the present optical film (1) can be obtained by using the compound (A) and the compound (3) as polymerizable liquid crystal compounds of the present composition (1) ) Mode, an IPS (in-plane switching) mode, an OCB (optically compensated bend) mode, a TN (twisted nematic) mode and an STN (super twisted nematic) mode.

2-1. Phase difference film

The retardation film, which is one type of optical film, is one of the preferred embodiments of the present optical film (1). The retardation film is used to convert linearly polarized light into circularly polarized light or elliptically polarized light, conversely convert circularly polarized light or elliptically polarized light into linearly polarized light, or convert polarized light of linearly polarized light.

As the retardation film 1, when the refractive index in the in-plane slow axis direction is n _x , the refractive index in the direction perpendicular to the in-plane slow axis (fast axis direction) is n _y , and the refractive index in the thickness direction is n _z , It is known that they can be categorized together. In other words,

a positive A plate with n _x & gt _; n _y & lt _; = n _z ,

a negative C plate of n _x ? n _y &gt; n _z ,

a positive C plate of n _x ? n _y &lt; n _z ,

a positive O plate and a negative O plate of n _x ≠ n _y ≠ n _z .

The retardation value of the retardation film 1 may be appropriately selected from 30 to 300 nm depending on the display device to be used.

When the retardation film 1 is used as a wide-band lambda / 4 plate, Re (549) may be adjusted to 113 to 163 nm, preferably 130 to 150 nm. When used as a broadband? / 2 plate, Re (549) may be adjusted to 250 to 300 nm, preferably 265 to 285 nm. If the retardation value is the above-mentioned value, it is preferable because the polarizing conversion tends to be uniformly performed for light of a wide wavelength. The broadband? / 4 plate is a retardation film that expresses a quarter-wave retardation value with respect to light of each wavelength, and the broadband? / 2 plate is a retardation film that expresses a 1/2 retardation value with respect to light of each wavelength Phase difference film.

On the other hand, the film thickness can be adjusted so as to give a desired retardation by adjusting the content of the polymerizable liquid crystal compound contained in the composition (1) appropriately. The retardation value (retardation value, Re ()) of the resulting retardation film is determined according to the following equation (4), so that it is sufficient to adjust Δn (λ) and film thickness d to obtain a desired Re (λ).

Re (?) = D x? N (?) (4)

D represents the thickness of the film, and? N (?) Represents the birefringence at the wavelength? Nm). In the formula, Re (?) Represents the retardation value at the wavelength? Nm, d represents the film thickness,

2-2. Production method of the present optical film (1)

The optical film (1) can be produced by preparing a suitable substrate, applying the composition (1) on a substrate and drying the polymerizable liquid crystal compound contained in the composition (1).

2-2-0. materials

As the substrate usable in the production of the present optical film, for example, glass, a plastic sheet, a plastic film and a light-transmitting film are preferable. Examples of the translucent film include polyolefin films such as polyethylene, polypropylene and norbornene polymers; Polyvinyl alcohol film; Polyethylene terephthalate film; Polymethacrylic acid ester film; Polyacrylate film; Cellulose ester film; Polyethylene naphthalate film; Polycarbonate film; Polysulfone film; Polyethersulfone film; Polyether ketone films; Polyphenylene sulfide film, and polyphenylene oxide film.

The substrate used for producing the optical film (1) is preferably made of a material having a hydroxyl group, and more preferably a film made of a material having a hydroxyl group. The film made of a material having a hydroxyl group may be a film obtained by forming a material having a hydroxyl group, or may be formed by forming a film (a precursor film) of a material having a hydroxyl group and then modifying the precursor contained in the precursor film with a hydroxyl group . Such modifications include, for example, plasma treatment under vacuum or atmospheric pressure, laser treatment, ozone treatment, saponification treatment, or flame treatment. Further, a primer treatment in which a film made of a material having no hydroxyl group or its precursor group is prepared and a coupling agent is applied to the surface of the film, a polymer having a hydroxyl group-containing monomer or hydroxyl group is attached to the surface and then irradiated with radiation, plasma, And then carrying out graft polymerization. A film in which a material having a hydroxyl group is arranged on the surface of the film is also referred to as a film made of a material having a hydroxyl group. When a film (substrate) made of a material having a hydroxyl group is used, the adhesion between the substrate and the optical film tends to be higher.

Among films (substrates) made of a material having a hydroxyl group, a film obtained by saponifying a triacetylcellulose film is preferable. The triacetylcellulose film is saponified to saponify the triacetylcellulose in the film to easily obtain a film made of a material having a hydroxyl group and is particularly preferable from the viewpoint of cost and handling in production.

It is preferable that an alignment film is provided on the surface of the substrate used for producing the present optical film (1), on which the present optical film is to be formed. The polymerizable liquid crystal compound in the present optical film can be aligned in a desired direction in accordance with the alignment direction of the alignment film, and then the polymerizable liquid crystal compound can be polymerized. When a substrate made of a material having a hydroxyl group is used, an alignment film may be provided on the substrate.

2-2-1. Production of non-polymerized film

By applying this composition (1) on a substrate or on an alignment film, a non-polymerized film can be obtained on the substrate. When the unpolymerized film shows a liquid crystal phase such as a nematic phase, it has birefringence due to mono-domain orientation.

Examples of the application method of the composition (1) on a substrate include extrusion coating method, direct gravure coating method, reverse gravure coating method, CAP (cap) coating method, die coating method, ink jet method, dip coating method, slit coating method, Spin coating and application by a bar coater.

Among them, in view of being able to continuously apply the composition on a substrate in a roll-to-roll manner, it is preferable to use a CAP coating method, an inkjet method, a dip coating method, a slit coating method, Application is preferred.

The present optical film (1) may be handled in a laminated state with a substrate. By laminating the base material on the present optical film, breakage of the present optical film is suppressed and the film can be handled easily when transporting or storing the film.

When the present composition (1) is coated on the orientation film after the alignment film is formed on the substrate in advance, it is not necessary to control the refractive index by stretching the optical film (1), and therefore the in-plane variation of birefringence becomes small. Therefore, a large main optical film that can cope with the enlargement of the flat panel display device (FPD) can be manufactured.

As a method for forming the alignment film, a method using an orienting polymer imparting alignment restraining force by rubbing (hereinafter, referred to as "rubbing method" in some cases), a method using an optically orienting polymer imparted with an alignment restricting force by irradiating polarized light A method of obliquely depositing silicon oxide on the surface of the substrate, and a Langmuir-Blodgett method (LB method), a monomolecular film having a long-chain alkyl group And the like. Among them, the photo alignment method is more preferable from the viewpoints of the alignment uniformity of the polymerizable liquid crystal compound contained in the composition (1), the processing time for producing the present optical film, and the processing cost. As the orientation film, it is preferable that even when the present composition is applied thereon, the composition contained in the present composition (1), for example, a solvent having such a degree of solubility as not to be dissolved in the solvent contained in the present composition (1) is preferable. In addition, the alignment film is required to have a heat resistance against the removal of the solvent from the undried film or the heat treatment for alignment of the polymerizable liquid crystal compound in the liquid crystal alignment.

The photo alignment method is as described in the second embodiment of the present invention.

The thickness of the alignment film formed on the substrate is, for example, 10 nm to 10000 nm, preferably 10 nm to 1000 nm. Within this range, the polymerizable liquid crystal compound contained in the present composition (1) can be oriented at a desired angle.

2-2-2. Polymerization of uncopolymerized film

The present optical film (1) can be obtained by polymerizing and curing a polymerizable liquid crystal compound contained in a non-polymerized film formed on a substrate or an alignment film. In the present optical film (1), the alignment property of the polymerizable liquid crystal compound is fixed, and it is hardly affected by the change of birefringence due to heat.

As a method of polymerizing the polymerizable liquid crystal compound, a photopolymerization method is preferable. According to the photopolymerization method, since the polymerization can be carried out at a low temperature, the range of heat resistance of the substrate to be used can be widened. The photopolymerization reaction is carried out by irradiating visible light, ultraviolet light or laser light to the unpolymerized film. Ultraviolet light is particularly preferable in terms of handling.

The uncopolymerized film formed by coating the composition (1) on the substrate or the alignment film may be irradiated with light as it is to cure the uncopolymerized film, but it is preferable to dry the uncopolymerized film to remove the solvent from the uncopolymerized film Do.

The removal of the solvent may be carried out in parallel with the polymerization reaction, but it is preferable to remove the solvent before the polymerization. Examples of the removing method include natural drying, air drying, heat drying or vacuum drying, or a combination thereof. Among them, natural drying or heat drying is preferred, and the temperature at the time of naturally drying or heating and drying is preferably 0 ° C to 250 ° C, more preferably 50 ° C to 220 ° C, and even more preferably 80 ° C to 170 ° C . The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes. If the heating temperature and the heating time are within the above ranges, those having insufficient heat resistance as the base material can be used.

By peeling the substrate, a film (laminated film) in which the alignment film and the present optical film are laminated can be obtained. Further, the orientation film is peeled off to obtain a single-layer original optical film (1). Alternatively, another substrate (film or plate) may be bonded to the laminated film, and the substrate or the alignment film laminated on the optical film 1 may be peeled off to transfer the film.

3. Polarizer

The present optical film (1) can be used for producing a polarizing plate. The polarizing plate of the present invention has at least one present retardation film (1). A polarizing plate using this retardation film (1) will be described.

1 (a) to 1 (e), the polarizing plate 4a (FIG. 1 (a)) in which the present retardation film 1 and the polarizing film layer 2 are directly laminated, ; (2) a polarizing plate 4b (Fig. 1 (b)) in which the present retardation film 1 and the polarizing film layer 2 are bonded via an adhesive layer 3 '; (3) A polarizing plate 4c (Fig. 1 (c)) in which the present retardation film 1 and the present retardation film 1 'are laminated and the present retardation film 1' and the polarizing film layer 2 are laminated, ); (4) A polarizing plate (1) obtained by bonding the present retardation film (1) and the present retardation film (1 ') via an adhesive layer (3) and further laminating the polarizing film layer 4d) (Fig. 1 (d)); And (5) the present retardation film 1 and the present retardation film 1 'are bonded to each other through the adhesive layer 3 and the present retardation film 1' and the polarizing film layer 2 are bonded to the adhesive layer 3 ' (Fig. 1 (e)) attached to each other via a polarizing plate 4e. The adhesive is collectively referred to as an adhesive and / or an adhesive.

The polarizing film layer 2 may be a film having a polarizing function. For example, a film or a polyvinyl alcohol film stretched by adsorbing iodine or a dichroic dye to a polyvinyl alcohol film is stretched to adsorb an oxo or a dichroic dye Film and the like.

The polarizing film layer 2 may also be provided with a film to be a protective film, if necessary. Examples of the protective film include a polyolefin film such as polyethylene, polypropylene and norbornene polymer, a polyethylene terephthalate film, a polymethacrylic acid ester film, a polyacrylic acid ester film, a cellulose ester film, a polyethylene naphthalate film, a polycarbonate film, Film, a polyethersulfone film, a polyether ketone film, a polyphenylene sulfide film, and a polyphenylene oxide film.

The adhesive used for the adhesive layer 3 and the adhesive layer 3 'is preferably an adhesive having high transparency and excellent heat resistance. As such an adhesive, for example, an acrylic adhesive, an epoxy adhesive or a urethane adhesive is used.

Further, in the polarizing plate, as shown in Figs. 1 (c) to 1 (e), two or more of the present retardation films 1 including the present optical film 1 may be bonded directly or through an adhesive layer.

4. Flat panel display

The flat panel display of the present invention includes the present optical film (1) and is very useful as a member according to a flat panel display. For example, a liquid crystal display device including a liquid crystal panel in which the present optical film 1 and a liquid crystal panel are bonded, and an organic electroluminescence (hereinafter also referred to as &quot; EL &quot;) panel in which the present optical film 1 and a light- For example, an organic EL display device.

4-1. Liquid crystal display

Examples of the liquid crystal display device of the present invention include liquid crystal display devices such as those shown in Figs. 2A and 2B. The liquid crystal display 10a shown in Fig. 2 (a) is obtained by bonding the polarizing plate 4 of the present invention and the liquid crystal panel 6 via the adhesive layer 5. The liquid crystal display 10a shown in Fig. The apparatus 10b is obtained by bonding the polarizing plate 4 of the present invention and the polarizing plate 4 'of the present invention to both sides of the liquid crystal panel 6 via the adhesive layer 5 and the adhesive layer 5'. According to the above configuration, the orientation of the liquid crystal molecules is changed by applying a voltage to the liquid crystal panel using an electrode (not shown), so that monochrome display can be performed.

4-2. Organic EL display device

Examples of the organic EL display device of the present invention include the organic EL display device shown in Fig. As the organic EL display device, an organic EL display device 11 in which a polarizing plate 4 of the present invention and an organic EL panel 7 are bonded to each other through an adhesive layer 5 can be mentioned. The organic EL panel 7 is at least one layer made of a conductive organic compound. According to the above configuration, by applying a voltage to the organic EL panel using an electrode (not shown), a compound contained in the light-emitting layer of the organic EL panel can emit light to display monochrome.

On the other hand, in the organic EL display device 11, the polarizing plate 4 preferably functions as a broadband circularly polarizing plate. It is possible to prevent reflection of external light on the surface of the organic EL display device 11 as long as it functions as a wide-band circularly polarizing plate.

INDUSTRIAL APPLICABILITY According to the present invention, it is possible to provide an optical film production method and optical film using a composition and a composition for producing an optical film excellent in adhesion.

II. Second Embodiment of the Present Invention

1. The second composition of the present invention (hereinafter, the second composition of the present invention may be referred to as "present composition (2)" as occasion demands, and the optical film produced by this composition (2) 2) ")

The present composition (2) is a composition comprising (D) a photo-orientable polymer (hereinafter occasionally referred to as "polymer (D)") and (B) a compound having a carbon-carbon unsaturated bond and an active hydrogen- (Hereinafter referred to as &quot; compound (B) &quot;).

1-1. Polymer (D)

The polymer (D) is used for aligning the liquid crystal compound when the optically anisotropic layer is formed on the present optical film (2) made of the composition (2).

Examples of the method for forming the present optical film 2 (the main optical film 2 as the alignment film) used for aligning the liquid crystal compound include a method (rubbing method) of imparting an alignment restraining force to the polymer D by rubbing, And a method of imparting an alignment regulating force to the polymer (D) by irradiation (hereinafter referred to as &quot; photo alignment method &quot; Among them, from the viewpoints of the alignment uniformity of the liquid crystal compound, the treatment time and the treatment cost, the photo alignment method utilizing the ability of the polymer (D) contained in the composition (2) is preferable. In this case, it is preferable that the optical film (2) has a solvent resistance such that it is not dissolved even when a liquid crystal compound is applied. In manufacturing the optical film (2), it is also required to have a heat resistance against the removal of the solvent from the undried film or the heat treatment for orientation of the liquid crystal compound.

As the polymer (D), a polymer having a photosensitive structure is used. When the polymer (D) having a photosensitive structure is irradiated with the polarized light, the photosensitive structure of the irradiated portion is isomerized or crosslinked to orient the polymer (D), and the alignment control force is imparted to the obtained optical film (2). Examples of the photosensitive structure include an azobenzene structure, a maleimide structure, a chalcone structure, a cinnamic acid structure, a 1,2-vinylene structure, a 1,2-acetylene structure, a spiropyran structure, a spirobenzopyran structure and a pulled structure. The polymer (D) having a photosensitive structure may be used alone in the present composition (2) or in combination of two or more thereof. On the other hand, the polymer (D) can be obtained by chain polymerization, coordination polymerization or ring-opening polymerization using a monomer having a photosensitive structure, such as polycondensation with dehydration or deamination, radical polymerization, anion polymerization, cation polymerization and the like. Further, a plurality of monomers having another photosensitive structure may be used and copolymers thereof may be used. As the polymer (D), there can be mentioned, for example, Japanese Patent No. 4450261, Japanese Patent No. 4011652, Japanese Patent Application Laid-Open No. 2010-49230, Japanese Patent No. 4404090, Japanese Patent Application Publication No. 2007-156439, Japanese Patent Application Publication No. 2007-232934 And the photo-orientable polymer described above.

The polymer (D) is particularly preferable as long as it forms a crosslinked structure by light irradiation. If the polymer (D) forms a crosslinked structure, sufficient durability can be ensured when the optically anisotropic layer-forming composition is applied when the optically anisotropic layer is formed.

The content of the polymer (D) in the composition (2) is preferably from 0.1 to 30 mass%, more preferably from 0.2 to 15 mass%, based on the total mass of the composition (2).

The present optical film (2) can be produced by applying the composition (2) on a substrate. As the base material, mention may be made of those exemplified in the first aspect of the present invention.

In order to produce the present optical film (2) on a substrate, it is preferable to use the present composition (2) containing a solvent because the production of the present optical film becomes simple. Examples of the solvent to be contained in the present composition (2) include water and organic solvents. Examples of the organic solvent include the organic solvents exemplified in the first embodiment of the present invention. When the present composition (2) containing a solvent is used, the solvent may be used alone or in combination of a plurality of kinds.

When the composition (2) contains a solvent, its content is preferably 100 parts by mass to 20000 parts by mass, more preferably 200 parts by mass to 15,000 parts by mass, based on 100 parts by mass of the solid content of the composition (2). The solid content refers to the total amount of the components excluding the low volatility component such as a solvent in the present composition (2).

1-2. The compound (B)

Examples of the compound (B) include the same compounds as the compound (B) contained in the present composition (1) described in the first embodiment of the present invention.

The content of the compound (B) in the present composition (2) is preferably 0.01 to 10 mass%, more preferably 0.02 to 5 mass%, based on the total mass of the composition (2). Within the above range, the reactivity of the polymer (D) in the present composition (2) is not lowered.

2. The present optical film (2)

The present optical film (2) is preferably formed by crosslinking the polymer (D) contained in the present composition (2).

In order to form a coating film (non-dried film) for producing an optical film from the composition (2), the composition (2) is first applied onto a substrate. As a coating method on a substrate, there is a method of coating on the base material of the present composition (1) described in the first aspect of the present invention.

Subsequently, the coating film applied on the substrate is dried to remove low boiling point components such as a solvent contained in the coating film.

Examples of the drying method include natural drying, air drying, heat drying or vacuum drying, or a combination thereof. The drying temperature is preferably 10 to 250 캜, more preferably 25 to 200 캜. The drying time is preferably 5 seconds to 60 minutes, more preferably 10 seconds to 30 minutes. When the drying temperature and the drying time are within the above ranges, damage to the substrate can be suppressed when any of the substrates is used.

2-1. The present optical film as an orientation film

Of the present optical film (2), the polymer (D) that is crosslinked by polarized irradiation functions as an alignment film. Specifically, the present composition (2) containing a solvent is applied onto a substrate, and the resulting coating film is irradiated with polarized light to crosslink the polymer (D), whereby the resulting optical film (2) becomes an alignment film. It is preferable that the coated film (undried film) is dried and dried before being irradiated with polarized light.

(For example, linearly polarized ultraviolet rays) is applied on the coating film formed of the present composition (2) in order to impart the alignment regulating force by the photo alignment method. Polarization irradiation can be performed using, for example, an apparatus described in Japanese Patent Application Laid-Open No. 2006-323060. Further, a photomask corresponding to a plurality of desired regions is prepared on the coating film formed of the composition (2), and the irradiation of polarized light (for example, linearly polarized ultraviolet rays) through the photomask is repeated for each of the regions, . As the photomask, for example, a light-shielding pattern is formed on a film such as quartz glass, soda lime glass, or polyester. The portion covered with the light shielding pattern is shielded from the exposed light, and the portion not covered with the shielding light transmits the exposed light. Since the effect of thermal expansion is small, quartz glass is preferable as a base material used for a photomask.

An example of producing a patterned alignment film is given below. First, a first polarizing light having a first polarizing direction is irradiated through a first photomask (the remaining area is a light-shielding pattern) having a void portion corresponding to the first pattern region in a coating film formed of the composition (2) (First polarized light irradiation). The direction of the alignment regulating force of the first pattern region is made to correspond to the first polarization direction by the first polarized light irradiation. Subsequently, a second photomask having a gap portion corresponding to the second pattern region (the remaining region is a light-shielding pattern) is irradiated with a second polarization direction different from the first polarization direction Direction) (second polarized light irradiation). The direction of the alignment regulating force of the second pattern region is made to correspond to the second polarization direction by the second polarized light irradiation. This makes it possible to obtain an alignment film having a plurality of pattern regions different in the direction of the alignment regulating force from each other. Further, by repeating polarized light irradiation through three or more types of photomasks, it is possible to produce a patterned alignment film having three or more pattern regions whose directions of alignment restricting force are different from each other. In view of the reactivity of the polymer (D), it is preferable that the light irradiated for each polarized light irradiation is ultraviolet light.

The film thickness of the present optical film (2) is, for example, 10 nm to 10000 nm, preferably 10 nm to 1000 nm. Within the above range, the liquid crystal compound can be oriented at a desired angle when the optically anisotropic layer is formed on the optical film (2).

2-2. The phase difference film (2)

An optically anisotropic layer is formed on the optical film 2 to produce a retardation film (hereinafter referred to as &quot; the retardation film 2 &quot; in some cases). The composition for forming an optically anisotropic layer is hereinafter referred to as a &quot; composition for forming an optically anisotropic layer &quot;.

2-2-1. Liquid crystal compound

The optically anisotropic layer can be formed, for example, by orienting a liquid crystal compound, and the composition for forming an optically anisotropic layer includes such a liquid crystal compound, preferably a polymerizable liquid crystal compound. The composition for forming an optically anisotropic layer may contain one liquid crystal compound or two or more other liquid crystal compounds.

As the liquid crystal compound, for example, the polymerizable liquid crystal compound described in the first aspect of the present invention can be mentioned, and a compound containing a group represented by the formula (X1) is preferable.

2-2-2. additive

The composition for forming an optically anisotropic layer may contain, in addition to the liquid crystal compound, an additive such as a photopolymerization initiator, a polymerization inhibitor, a photosensitizer, a photopolymerization initiator, a solvent, and a chiral agent. In particular, it is preferable to include a solvent, particularly an organic solvent, in that the composition for forming the optically anisotropic layer itself is easily formed at the time of forming the optically anisotropic layer. When the liquid crystal compound is a polymerizable liquid crystal compound, it is preferable that the composition for forming an optically anisotropic layer contains a polymerization initiator having a function of curing the film on which the optically anisotropic layer-forming composition is formed.

As each additive, additives exemplified in the first embodiment of the present invention can be mentioned.

An unpolymerized film can be obtained on the optical film (2) by applying a composition for forming an optically anisotropic layer on the optical film (2). When the unpolymerized film shows a liquid crystal phase such as a nematic phase, it has birefringence due to mono-domain orientation.

As a method of applying the optically anisotropic layer-forming composition onto the present optical film (2), a method exemplified as a method of applying the present composition (2) on a substrate can be applied. Among them, the composition for forming an optically anisotropic layer can be applied on the optical film continuously viewed in a roll-to-roll manner. The optical anisotropic layer can be applied by a CAP coating method, an inkjet method, a dip coating method, a slit coating method, Application is preferred. For example, in the case of the roll-to-roll type, the present composition (2) is coated on a substrate to form the present optical film (2) on the substrate and the optically anisotropic layer .

The present optical film (2) may be used in a laminated state with a substrate. By laminating the base film on the optical film 2, breakage of the base film 2 when the film is transported or stored is suppressed and can be easily handled.

The present retardation film (2) can be obtained by polymerizing and curing a liquid crystal compound contained in a coating film (un polymerized film) for optically anisotropic layer formation formed on the optical film (2). In the retardation film (2), the orientation property of the liquid crystal compound is fixed, and it is hardly affected by the change of birefringence due to heat.

As a method for polymerizing and curing a liquid crystal compound, the method exemplified in the first embodiment of the present invention can be mentioned.

This retardation film (2) is one of the preferred embodiments of the use of the present optical film (2). This retardation film 2 is used for converting linearly polarized light into circularly polarized light or elliptically polarized light, or conversely converting circularly polarized light or elliptically polarized light into linearly polarized light or converting the polarization direction of linearly polarized light.

The properties of the present retardation film (2) are the same as those of the present retardation film (1) described in the first embodiment of the present invention.

4. Polarizer

The present optical film (2) can be used for producing a polarizing plate.

The polarizing plate may be the same as the polarizing plate described in the first embodiment of the present invention.

5. Flat panel display

The flat panel display of the present invention includes the present optical film (2).

The flat panel display device may be the same as the flat panel display device described in the first aspect of the present invention.

INDUSTRIAL APPLICABILITY According to the present invention, it is possible to provide an optical film production method and optical film using a composition and a composition for producing an optical film excellent in adhesion.

III. Third Embodiment of the Present Invention

A third aspect of the present invention is an optical film (hereinafter sometimes referred to as &quot; the present optical film (3) &quot;, &quot;Quot;).

1. Equipment

Examples of the substrate include those described in the first embodiment of the present invention.

It is more preferable that the substrate is a film (substrate) made of a material having a hydroxyl group described in the first embodiment of the present invention. When a film (substrate) made of a material having a hydroxyl group is used, the adhesiveness between the substrate A and the A layer tends to be higher in addition to the adhesion between the A layer / the B layer, so that the present optical film of higher quality can be obtained.

When a film made of a material obtained by saponifying triacetyl cellulose out of a film made of a material having a hydroxyl group is used, the adhesiveness between the substrate / A layer becomes better due to the synergistic effect with the composition (A). In addition, a film made of a material obtained by saponifying triacetyl cellulose is also preferable because it can easily obtain a film (triacetyl cellulose film) itself made of triacetyl cellulose, which is a precursor film thereof, on the market.

2. Composition (A)

The composition (A) is the composition (2) described in the second embodiment of the present invention. The photo-orientable polymer (D) in the composition (A) corresponds to the polymer (D) in the composition (2) and the carbon-carbon unsaturated bond (B-1) in the composition (A) Group corresponds to the compound (B) in the composition (2).

3. Composition (B)

The composition (B) is the composition (1) described in the first aspect of the present invention. The polymerizable liquid crystal compound in the composition (B) corresponds to the polymerizable liquid crystal compound in the composition (1), and the polymerizable liquid crystal compound in the composition (B) The compound corresponds to the compound (B) in the composition (1), and the photopolymerization initiator (C) in the composition (B) corresponds to the photopolymerization initiator (C) in the composition (1).

As the compound (B-1) and the compound (B-2), for example, the compound (2) is preferable, and commercially available Laromer (registered trademark) LR-9000 (manufactured by BASF). On the other hand, the compound (B-1) contained in the composition (A) may be the same or different from the compound (B-2) contained in the composition (B) When the compound (B-1) and the compound (B-2) are commercially available products such as Laromer LR-9000, the composition (A) and the composition (B) can be easily prepared.

4. This optical film

The present optical film (3) is a film which can transmit light and is a film having an optical function. The optical function means refraction, birefringence, and the like.

The optical film (3) is preferably excellent in transparency in the visible light region, and can be used as a member for various display devices, in particular, a member for a flat panel display device. The thickness of the optical film 3 can be appropriately adjusted depending on the use of the present optical film, and is preferably 0.1 to 10 탆, more preferably 0.2 to 5 탆 in terms of reducing photoelasticity.

The thickness of the substrate is preferably from 10 to 200 mu m, more preferably from 15 to 100 mu m. The thickness (film thickness) of the A layer is preferably 0.01 to 10 mu m (10 to 10000 nm), more preferably 0.01 to 1 mu m (10 to 1000 nm). The thickness (film thickness) of the B layer is, for example, 0.1 to 10 mu m, preferably 0.2 to 5 mu m.

When the present optical film (3) is used for a display device, the present optical film may be used as a single layer, or a plurality of the present optical films may be laminated to form a laminate or may be combined with other films. A viewing angle increasing film, a viewing angle increasing film, an antireflection film, a polarizing film, a circularly polarizing film, an elliptically polarizing film, and a luminance improving film by using the film in combination with another film. The present optical film may be a laminate of a plurality of kinds of base materials among specific examples of the base materials already mentioned, or may have a plurality of A layers or a plurality of B layers. On the other hand, for example, in the case of having a plurality of layers A, the composition (A) is formed on the base material, and the composition (A) is then formed on the first A layer, And a second A layer is formed by using the composition (A) different from the first composition.

Particularly, the optical film of the present invention can be used in a VA (Vertical Alignment) mode, an IPS (in-plane switching) mode, an OCB (optically compensated bend) mode, a TN a twisted nematic mode, a super twisted nematic (STN) mode, and the like.

4-1. Phase difference film

The retardation film is one of the preferred embodiments of the use of the present optical film (3).

Examples of the retardation film include the retardation film exemplified in the first embodiment of the present invention.

4-2. Method for producing the present optical film

The production method of the present optical film includes, for example, the following processes <1> to <4>. On the other hand, this production method is a method of using the composition (A) and the composition (B) both containing a solvent, and is a production method of the present optical film having one base material, one layer A and one layer B respectively.

&Lt; 1 > A step of forming a first coating film on a substrate (first coating film forming step) by applying the composition (A) onto a substrate;

&Lt; 2 > A step of converting the first coating film into an A layer by crosslinking (B-1) contained in the first coating film by (1) (A layer forming step);

&Lt; 3 > A step (second coating film forming step) of forming a second coating film on the layer A by applying the composition (B) on the layer A formed by the step (2);

&Lt; 4 > A step of polymerizing the polymerizable liquid crystal compound contained in the second coating film formed by < 3 > (B layer forming step)

The first coating film forming step is a step of preparing a substrate and coating the composition (A) on the substrate to form a first coating film on the substrate.

The application method of the composition (A) is exemplified by the method in the second aspect of the present invention.

In the A-layer formation step, the photo-orientable polymer contained in the first coating film formed on the substrate, preferably the dried first coating film, is photo-oriented (crosslinked) by the first coating film formation step, Thereby converting the first coating film into the A layer. The layer A functions as an alignment film (orientation layer) because it is given an alignment regulating force.

Examples of the drying method include those exemplified in the second embodiment of the present invention.

As a method for imparting the alignment regulating force by photo-alignment, the method exemplified in the second embodiment of the present invention can be mentioned.

The second coating film forming step is a step of forming a second coating film (non-polymerized film) by applying the composition (B) on the layer A formed in the A layer forming step. When the polymerizable liquid crystal compound contained in the second coating film exhibits a liquid crystal phase such as a nematic phase, it has birefringence due to mono-domain orientation.

The method of applying the composition (B) on the layer A in the second coating film forming step may be exemplified by the method in the first aspect of the present invention.

In the B layer forming step, the polymerizable liquid crystal compound contained in the second coating film formed on the A layer is polymerized and cured to obtain the present optical film (3). The orientation of the polymerizable liquid crystal compound in the B layer is fixed, and it is hardly affected by the change in birefringence due to heat. The adhesion between the A layer and the B layer can be improved by the effect of the compound (B-1) contained in the A layer or the first coating film and the compound (B-2) contained in the B layer or the second coating film And is very excellent.

As a method of polymerizing the polymerizable liquid crystal compound, a photopolymerization method is preferable. According to the photopolymerization method, since the polymerization can be carried out at a low temperature, the range of heat resistance of the substrate to be used can be widened. The photopolymerization reaction is carried out by irradiating visible light, ultraviolet light or laser light to the second coating film. Ultraviolet light is particularly preferable in terms of handling.

The second coating film formed by applying the composition (B) on the A layer can be irradiated with light as it is to form the B layer. However, the second coating film is dried to remove low volatility components such as a solvent from the second coating film It is preferable to remove the film.

On the other hand, the removal of the low-volatility component may be performed in parallel with the polymerization reaction, but it is preferable to remove most of the solvent before polymerization. As the removing method, the method exemplified as the drying method of the first coating film is employed. Among them, natural drying or heat drying is preferred, and the temperature at the time of naturally drying or heating and drying is preferably 0 ° C to 250 ° C, more preferably 50 ° C to 220 ° C, and even more preferably 80 ° C to 170 ° C . The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes. If the heating temperature and the heating time are within the above-mentioned range, it is possible to use those in which the substrate and / or the A layer are not necessarily sufficiently heat-resistant.

5. Use of the present optical film as a polarizing plate

The present optical film can be used as a retardation film in the production of a polarizing plate.

The polarizing plate may be the same as the polarizing plate described in the first embodiment of the present invention.

6. Flat panel display

The flat panel display of the present invention includes the present optical film (3).

The flat panel display device may be the same as the flat panel display device described in the first aspect of the present invention.

According to the present invention, it is possible to provide an optical film excellent in adhesion between the orientation layer and the optically anisotropic layer.

Example

The present invention will be described in more detail by way of examples. In the examples, &quot;% &quot; and &quot; part &quot; are parts by mass and parts by mass unless otherwise specified.

&Lt; First Aspect of Present Invention &

1. Synthesis Example of Polymerizable Liquid Crystal Compound

Compound (A11-1) was synthesized according to the following reaction formula.

1-1. Synthesis of 4,6-dimethylbenzofuran-2-carboxylic acid

146.6 g of 4,6-dimethylsalicylaldehyde and 330.7 g of potassium carbonate were dispersed in 700 mL of N, N'-dimethylacetamide. After the obtained dispersion was heated to 80 占 폚, 190.5 g of tert-butyl bromoacetate was added dropwise over 30 minutes. The dropwise addition mixture was allowed to react at 130 DEG C for 2 hours. After the reaction solution was cooled to room temperature, 600 mL of methyl isobutyl ketone was added and the reaction solution was washed with 1200 mL of pure water. The organic layer was washed twice with 1000 mL of pure water and the organic layer was recovered. After dehydration with anhydrous sodium sulfate, the solvent was distilled off with an evaporator. The residue was dissolved in 240 g of acetic acid, 72 g of a hydrobromic acid aqueous solution was added, and the mixture was stirred at 40 占 폚 for 1 hour. After allowing to cool to room temperature, 150 g of 1 N (1 mol / L) -hydrochloric acid was added, and the precipitated white powder was filtered off. The resulting white powder was further washed with 1N-hydrochloric acid and then vacuum-dried to obtain 81.7 g of 4,6-dimethylbenzofuran-2-carboxylic acid as a yellow powder. The yield was 44% based on 4,6-dimethyl salicylaldehyde.

1-2. Synthesis of compound (11-a)

80 g of 4,6-dimethylbenzofuran-2-carboxylic acid, 96.6 g of 2,5-dimethoxyaniline and 400 g of chloroform were mixed. After the obtained suspension was cooled with an ice bath, a mixture of 88.7 g of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride and 300 g of chloroform was added over 4 hours, followed by reaction at room temperature for 48 hours. The obtained mixed solution was concentrated, and crystallized by adding a mixed solution of 1 N hydrochloric acid and water-methanol (2 parts by volume of water, 1 part by volume of methanol). The resulting precipitate was collected by filtration, and a mixed solution of water and methanol (2 parts by volume of water and 1 part by volume of methanol) was added. The precipitated pale yellow precipitate was collected by filtration, washed with a mixed solution of water and methanol (2 parts by volume of water, 1 part by volume of methanol) and vacuum-dried to obtain 124.2 g of a compound (11-a) as a pale yellow powder. The yield was 91% based on 4,6-dimethylbenzofuran-2-carboxylic acid.

1-3. Synthesis of Compound (11-b)

123 g of the compound (11-a), 9.2 g of 2,4-bis (4-methoxyphenyl) -1,3-dithia-2,4-diphosphetane- 1200 g of toluene were mixed. The obtained mixed solution was heated to 110 DEG C and then reacted at the same temperature for 8 hours. After cooling to room temperature, it was washed with 1 N aqueous sodium hydroxide solution. The organic layer was recovered, and 800 mL of n-heptane was added. The precipitated yellow precipitate was collected by filtration, washed with n-heptane and dried under vacuum to obtain 109.2 g of a compound (11-b) as a pale yellow powder. The yield was 85% based on compound (11-a).

1-4. Synthesis of Compound (11-c)

60 g of the compound (11-b), 53.8 g of potassium hydroxide and 1000 g of water were mixed. The obtained mixed solution was stirred under ice-cooling. Subsequently, 133 g of potassium ferricyanide and 51 g of methanol were added and reacted. The reaction was allowed to proceed at room temperature for 36 hours, and the precipitated yellow precipitate was filtered off. The resulting precipitate was washed with a mixed solvent of n-heptane-toluene (3 volumes of n-heptane, 1 volume of toluene) and the resulting yellow powder was vacuum-dried to obtain 51.3 g of a compound (11-c) . The yield was 86% based on compound (11-b).

1-5. Synthesis of Compound (11-d)

40 g of the compound (11-c) and 400 g (10 times mass) of pyridinium chloride were mixed, the temperature of the resulting mixture was raised to 180 캜, and the mixture was allowed to react at the same temperature for 3 hours. The resulting mixed solution was added to ice, and the precipitated precipitate was collected by filtration. The suspension was washed with water, washed with toluene and vacuum-dried to obtain 36.6 g of a yellow solid containing the compound (11-d) as a main component. The yield was 99% based on the compound (11-c).

1-6. Synthesis of Compound (R-1a)

Compound (R-1a) was synthesized with reference to paragraph 0244 of Japanese Patent Application Laid-Open No. 2010-31223.

1-7. Synthesis of Compound (A11-1)

35 g of the compound (11-d), 98.8 g of the compound (R-1a), 1.37 g of dimethylaminopyridine and 700 mL of toluene were mixed. 55.6 g of N, N'-dicyclohexylcarbodiimide was added to the obtained mixed solution under ice-cooling. The obtained reaction solution was allowed to react at room temperature overnight, filtered using a filter material pre-coated with silica gel, and then concentrated under reduced pressure. Methanol was added to the residue to crystallize. Crystals were filtered off, redissolved in chloroform, and 2.3 g of activated carbon was added, followed by stirring at room temperature for one hour. The solution was filtered, and the filtrate was concentrated under reduced pressure to a volume of 1/3 by an evaporator. Methanol was added with stirring, and the precipitated white precipitate was collected by filtration, washed with heptane and vacuum dried to obtain Compound (A11-1) To obtain 74.5 g as a white powder. The yield was 60% based on the compound (11-d).

1-8. Synthesis of Compound (ix-1)

Compound (ix-1) was synthesized by the method described in JP-A-2010-31223.

1-9. Synthesis of photo-orientable polymer (Z)

The photo-orientable polymer (Z) was obtained from Macromol. Chem. Phys. 197, 1919-1935 (1996).

1.5 parts of the monomer (Z-a) represented by the formula (Z-a) and 0.1 part of methyl methacrylate were dissolved in 16 parts of tetrahydrofuran and reacted at 60 ° C for 24 hours. Subsequently, the reaction solution was allowed to cool to room temperature, and then dropped into a mixture of toluene and methanol to obtain a photo-orientable polymer (Z). The number average molecular weight of the photo-orientable polymer (Z) was 33,000. The content of the structure derived from the monomer (Z-a) in the photo-orientable polymer (Z) was 75 mol%.

The polystyrene reduced number average molecular weight (Mn) of the obtained photo-orientable polymer (Z) was measured by the GPC method under the following conditions.

Device; HLC-8220 GPC (manufactured by Tosoh Corporation)

column; TOSOH TSKgel Multipore H _XL -M

Column temperature; 40 ℃

menstruum; THF (tetrahydrofuran)

Flow rate; 1.0 mL / min

Detector; RI

Calibration standards; TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-5000, A-500

2. Preparation of composition

Each component shown in the table was mixed, and the resulting solution was stirred at 80 DEG C for 1 hour and then cooled to room temperature to prepare a composition.

Irg 369 (Irgacure 369 (BASF Japan)) was used as the photopolymerization initiator, and BYK361N (manufactured by Beck Chemie Japan) was used as the leveling agent. The polymerizable liquid crystal compound (LC242) is manufactured by BASF, and is a compound of the following formula.

3. Production Example of Optical Film

A 5% toluene solution of photo-orientable polymer (Z) was applied on the saponified triacetylcellulose film, dried, and a film with a thickness of 300 nm was formed. Subsequently, linearly polarized light (polarized UV irradiation) was irradiated for 5 minutes at an illuminance of 15 mW / cm 2 using a spot cure SP-7 (manufactured by Ushio Denki Co., Ltd.) equipped with a polarizing UV irradiation jig in a direction perpendicular to the surface, did. The composition shown in the table was coated on the side subjected to polarized UV irradiation using a bar coater and heated to 130 캜 to obtain a film oriented in a liquid crystal phase. Thereafter, the optical film was irradiated with ultraviolet rays at a wavelength of 365 nm at an illuminance of 40 mW / cm 2 for 1 minute by using Unicure (VB-15201BY-A, manufactured by Ushio DENKI Co., Ltd.) .

[Evaluation of adhesion]

The peel resistance was evaluated using a cross-cut guide I series (CCI-1, 1 mm interval, 25 masses) manufactured by Koechec Co., Ltd. according to JIS-K5600, and the remaining number of liquid crystal layers was counted. The results are shown in the table. It was confirmed that the present optical film had excellent adhesion.

[Measurement of optical characteristics]

The retardation value of the optical film was measured by a measuring device (KOBRA-WR, manufactured by Oji Paper Co., Ltd.). The retardation value was measured at a wavelength (?) Of 549 nm. The results are shown in the table.

Remaining number after peeling test Re (549) Example 1 18 142.8 Example 2 17 141.0 Example 3 19 144.9 Comparative Example 1 0 143.0

&Lt; Second embodiment of the present invention &

1. Synthetic Example

&Quot; 1-9 &quot; in the first embodiment of the present invention. Synthesis of Photo Orientation Polymer (Z) &quot; was used to synthesize the photo-orientable polymer (Z).

2. Preparation of composition

Each component shown in the table was mixed, and the obtained solution was stirred at 80 DEG C for 1 hour and then cooled to room temperature to prepare a composition.

Laromer (registered trademark) LR-9000 (manufactured by BASF Japan) was used as the compound (B).

Irg 369 (Irgacure 369 (BASF Japan)) was used as the photopolymerization initiator, and BYK361N (manufactured by Beck Chemie Japan) was used as the leveling agent. LC242 is manufactured by BASF, and is a compound of the following formula.

3. Production Example of Optical Film

The compositions shown in Examples 3 and 4 and Comparative Example 2 were coated on the saponified triacetylcellulose film and dried to form a film having a thickness of 280 nm. Subsequently, linearly polarized light was irradiated for 5 minutes at an illuminance of 15 mW / cm 2 using a spot cure SP-7 (manufactured by Ushio DENKI K.K.) equipped with a polarizing UV irradiation jig in a direction perpendicular to the surface. The composition for optically anisotropic layer formation shown in the table was coated on the side subjected to polarized UV using a bar coater and heated at 120 캜 to obtain a film oriented in a liquid crystal phase. Thereafter, the optical film was irradiated with ultraviolet rays at a wavelength of 365 nm at an illuminance of 40 mW / cm 2 for 1 minute by using Unicure (VB-15201BY-A, manufactured by Ushio DENKI Co., Ltd.) .

[Evaluation of adhesion]

The peel resistance was evaluated using a cross-cut guide I series (CCI-1, 1 mm interval, 25 masses) manufactured by Koechec Co., Ltd. according to JIS-K5600, and the remaining number of liquid crystal layers was counted. The results are shown in the table. It was confirmed that the present optical film had excellent adhesion.

[Measurement of optical characteristics]

The retardation value of the optical film was measured by a measuring device (KOBRA-WR, manufactured by Oji Paper Co., Ltd.). The retardation value was measured at a wavelength (?) Of 549 nm. The results are shown in the table.

&Lt; Third embodiment of the present invention &

1. Synthetic Example

&Quot; 1-9 &quot; in the first embodiment of the present invention. Synthesis of Photo Orientation Polymer (Z) &quot; was used to synthesize the photo-orientable polymer (Z).

2. Preparation of composition

Each component shown in the table was mixed, and the obtained solution was stirred at 80 DEG C for 1 hour and then cooled to room temperature to prepare a composition.

Laromer (registered trademark) LR-9000 (manufactured by BASF Japan) was used as the compound (B-1).

Irg 369 (Irgacure 369 (BASF Japan)) was used as the photopolymerization initiator, and BYK361N (manufactured by Beck Chemie Japan) was used as the leveling agent. LC242 is manufactured by BASF, and is a compound of the following formula.

3. Production Example of Optical Film

The composition (A-1) was coated on the saponified triacetylcellulose film and dried to form a film having a thickness of 280 nm. Subsequently, linearly polarized light was irradiated for 5 minutes at an illuminance of 15 mW / cm 2 using a spot cure SP-7 (made by Ushio Denki Co., Ltd.) equipped with a polarizing UV irradiation jig in a direction perpendicular to the surface. Composition (B-1) was coated on the side subjected to polarized UV using a bar coater and heated to 120 캜 to obtain a film oriented in a liquid crystal phase. Thereafter, the optical film was irradiated with ultraviolet rays at a wavelength of 365 nm at an illuminance of 40 mW / cm 2 for 1 minute by using Unicure (VB-15201BY-A, manufactured by Ushio DENKI Co., Ltd.) .

[Evaluation of adhesion]

The peel resistance was evaluated using a cross-cut guide I series (CCI-1, 1 mm interval, 25 masses) manufactured by Koechec Co., Ltd. according to JIS-K5600, and the remaining number of liquid crystal layers was counted. The results are shown in the table. It was confirmed that the present optical film had excellent adhesion.

[Measurement of optical characteristics]

The retardation value of the optical film was measured by a measuring device (KOBRA-WR, manufactured by Oji Paper Co., Ltd.). The retardation value was measured at a wavelength (?) Of 549 nm. The results are shown in the table.

INDUSTRIAL APPLICABILITY The present invention is very useful for the production of an optical film used for a liquid crystal display device, an organic EL display device, and the like, and has high industrial value.

1, 1 ', 12: present retardation film 2: polarizing film layer
3, 3 ': adhesive layer 4a, 4b, 4c, 4d, 4e, 4, 4'
5, 5 ': adhesive layer 6: liquid crystal panel
7: organic EL panel 10a, 10b: liquid crystal display
11: organic EL display device

Claims (39)

A composition comprising (A), (B) and (C)
(A) a polymerizable liquid crystal compound
(B) a compound having a carbon-carbon unsaturated bond and an active hydrogen-reactive group in the molecule
(C) a photopolymerization initiator. The composition according to claim 1, wherein (B) is a compound having an isocyanato group as an active hydrogen-reactive group. The composition according to claim 1, wherein (B) is a compound represented by the following formula (X).

[In the formula (X), n represents an integer of 1 to 10, and R ^{1 '} represents a divalent aliphatic or alicyclic hydrocarbon group having 2 to 20 carbon atoms or a divalent aromatic hydrocarbon group having 5 to 20 carbon atoms. The two R ^{2 '} groups in each repeating unit are -NH- on one side and the group represented by - [NC (═O) -R ^3' ] - on the other. R ^{3 '} represents a group having a hydroxyl group or a carbon-carbon unsaturated bond.
Among R ^{3 '} , at least one R ^3' is a group having a carbon-carbon unsaturated bond. The composition according to any one of claims 1 to 3, wherein (A) is a compound represented by the formula (A).

[In the formula (A), X ¹ represents an oxygen atom, a sulfur atom or -NR ¹ -. R ¹ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
Y ¹ represents a monovalent aromatic hydrocarbon group having 6 to 12 carbon atoms, which may have a substituent, or a monovalent aromatic heterocyclic group having 3 to 12 carbon atoms, which may have a substituent.
Q ³ and Q ⁴ each independently represent a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, a monovalent group having 6 to 20 carbon atoms An aromatic hydrocarbon group, a halogen atom, a cyano group, a nitro group, -NR ² R ³ or -SR ² , or Q ³ and Q ⁴ are bonded to each other to form an aromatic ring or aromatic heterocyclic ring . R ² and R ³ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
D ¹ and D ² are each independently a single bond, -C (= O) -O-, -C (= S) -O-, -CR 4 R 5 -, -CR 4 R 5 -CR 6 R 7 - -O-CR ⁴ R ⁵ -, -CR ⁴ R ⁵ -O-CR ⁶ R ⁷ -, -CO-O-CR ⁴ R ⁵ -, -O-CO-CR ⁴ R ⁵ -, -CR ⁴ R ⁵ -O-CO-CR ⁶ R ⁷ -, -CR ⁴ R ⁵ -CO-O-CR ⁶ R ⁷ - or -NR ⁴ -CR ⁵ R ⁶ - or -CO-NR ⁴ -.
R ⁴ , R ⁵ , R ⁶ and R ⁷ each independently represent a hydrogen atom, a fluorine atom or an alkyl group having 1 to 4 carbon atoms.
G ¹ and G ² each independently represent a divalent alicyclic hydrocarbon group having 5 to 8 carbon atoms, and the methylene group constituting the alicyclic hydrocarbon group may be substituted with an oxygen atom, a sulfur atom or -NH-, and the alicyclic hydrocarbon The methine group constituting the group may be substituted with a tertiary nitrogen atom.
L ¹ and L ² each independently represent a monovalent organic group, and at least one of L ¹ and L ² is an organic group having a polymerizable group. The method according to claim 4, wherein (A)
Wherein L ^{1 in} formula (A) is a group represented by formula (A1), and L ² is a group represented by formula (A2).
P ¹ -F ¹ - (B ¹ -A ¹ ) _k -E ¹ - (A1)
P ² -F ² - (B ² -A ² ) ₁ -E ² - (A2)
B ¹ , B ² , E ¹ and E ² each independently represent -CR ⁴ R ⁵ -, -CH ₂ -CH ₂ -, -O-, -S-, -CO-O-, -O-CO- O-, -CS-O-, -O-CS-O-, -CO-NR 1 -, -O-CH 2 -, -S-CH 2 - or a single Lt; / RTI &gt;
A ¹ and A ² each independently represent a divalent alicyclic hydrocarbon group having 5 to 8 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms and the methylene group constituting the alicyclic hydrocarbon group is an oxygen atom, -, and the methine group constituting the alicyclic hydrocarbon group may be substituted with a tertiary nitrogen atom.
k and l each independently represent an integer of 0 to 3; When k is an integer of 2 or more, plural B ^{1 s} may be the same or different, and plural A ^{1 s} may be the same or different. When l is an integer of 2 or more, the plurality of B ² may be the same or different, and the plurality of A ² may be the same or different.
F ¹ and F ² represent a divalent aliphatic hydrocarbon group having 1 to 12 carbon atoms.
P ¹ represents a polymerizable group.
P ² represents a hydrogen atom or a polymerizable group.
R ¹ , R ⁴ and R ⁵ have the same meaning as above.] An optical film formed by polymerizing a polymerizable liquid crystal compound contained in the composition according to any one of claims 1 to 5. A process for producing an optical film comprising the following (1) and (2):
(1) a step of applying the composition described in any one of claims 1 to 5 onto a substrate;
(2) A process for forming an optical film by polymerizing a polymerizable liquid crystal compound contained in a coating film applied on a substrate by (1). The method for producing an optical film according to claim 7, wherein the substrate is made of a material having a hydroxyl group. The process for producing an optical film according to claim 8, wherein the material having a hydroxyl group is a material obtained by saponifying triacetyl cellulose. 10. The method of producing an optical film according to any one of claims 7 to 9, wherein the substrate is provided with an alignment film formed on the surface thereof with a photo-orientable polymer. The method for producing an optical film according to claim 10, wherein the alignment film is formed by forming a crosslinking structure by photoirradiation of a photo-orientable polymer. An optical film obtained by the production method according to any one of claims 7 to 11. The optical film according to claim 6 or 12, wherein the optical film has a retardation. A polarizing plate comprising the optical film according to any one of claims 6, 12 and 13. A flat panel display device comprising the optical film according to any one of claims 6, 12 and 13. A composition comprising (D) and (B)
(D) photo-orientable polymer
(B) a compound having a carbon-carbon unsaturated bond and an active hydrogen-reactive group in a molecule. The composition according to claim 16, wherein (D) is a photo-orientable polymer capable of forming a crosslinked structure by light irradiation. The composition according to claim 16 or 17, wherein (B) is a compound having an isocyanato group as an active hydrogen-reactive group. The composition according to claim 16 or 17, wherein (B) is a compound represented by the following formula (X).

[In the formula (X), n represents an integer of 1 to 10, and R ^{1 '} represents a divalent aliphatic or alicyclic hydrocarbon group having 2 to 20 carbon atoms or a divalent aromatic hydrocarbon group having 5 to 20 carbon atoms. The two R ^{2 '} groups in each repeating unit are -NH- on one side and the group represented by - [NC (═O) -R ^3' ] - on the other. R ^{3 '} represents a group having a hydroxyl group or a carbon-carbon unsaturated bond.
Among R ^{3 '} , at least one R ^3' is a group having a carbon-carbon unsaturated bond. An optical film formed by crosslinking a photo-orientable polymer contained in the composition according to any one of claims 16 to 19. A process for producing an optical film comprising the following (1) and (2):
(1) a step of applying the composition described in any one of claims 16 to 19 on a substrate;
(2) A step of forming an optical film by crosslinking the photo-orientable polymer contained in the coating film applied on the substrate by (1). The method for producing an optical film according to claim 21, wherein the substrate is made of a material having a hydroxyl group. The method for producing an optical film according to claim 22, wherein the material having a hydroxyl group is a material obtained by saponifying triacetyl cellulose. An optical film obtained by the production method according to any one of claims 21 to 23. An optical retardation film comprising an optical anisotropic layer formed on the optical film according to claim 20 or 24. A polarizing plate comprising the optical film according to claim 20 or 24. A flat panel display device comprising the optical film according to claim 20 or 24. An optical film comprising a substrate, an A layer formed of the composition (A), and a B layer formed of the composition (B) in this order,
The composition (A) contains the following (D) and (B-1) and the composition (B) is an optical film containing the following (A), (B-
(D) photo-orientable polymer
(B-1) a compound having a carbon-carbon unsaturated bond and an active hydrogen-reactive group
(A) a polymerizable liquid crystal compound
(B-2) a compound having a carbon-carbon unsaturated bond and an active hydrogen-reactive group
(C) a photopolymerization initiator. 29. The optical film according to claim 28, wherein (D) is a photo-orientable polymer capable of forming a crosslinked structure by light irradiation. The optical film according to claim 28 or 29, wherein (B-1) and (B-2) are compounds having an isocyanato group as an active hydrogen-reactive group. The optical film according to claim 28 or 29, wherein (B-1) and (B-2) are each independently a compound represented by the following formula (X).

[In the formula (X), n represents an integer of 1 to 10, and R ^{1 '} represents a divalent aliphatic or alicyclic hydrocarbon group having 2 to 20 carbon atoms or a divalent aromatic hydrocarbon group having 5 to 20 carbon atoms. The two R ^{2 '} groups in each repeating unit are -NH- on one side and the group represented by - [NC (═O) -R ^3' ] - on the other. R ^{3 '} represents a group having a hydroxyl group or a carbon-carbon unsaturated bond.
Among R ^{3 '} , at least one R ^3' is a group having a carbon-carbon unsaturated bond. The optical film according to any one of claims 28 to 31, wherein the layer A is formed by crosslinking (D) contained in the composition (A). The optical film according to any one of claims 28 to 32, wherein the substrate is made of a material having a hydroxyl group. The optical film according to claim 33, wherein the material having a hydroxyl group is a material obtained by saponifying triacetyl cellulose. 35. The optical film according to any one of claims 28 to 34, which has retardation. A process for producing an optical film comprising the following steps < 1 > to < 4 &
&Lt; 1 > A method for manufacturing a semiconductor device, comprising: forming a first coating film on a substrate by applying a composition (A) containing the following (D) and (B-1)
(D) photo-orientable polymer
(B-1) a compound having a carbon-carbon unsaturated bond and an active hydrogen-reactive group
(2) a step of converting the first coating film into an A layer by crosslinking (D) contained in the first coating film applied on the substrate by the method (1);
(3) a step of forming a second coating film on the layer A by applying a composition (B) containing the following (A), (B-2) and (C) on the layer A formed by the step (2);
(A) a polymerizable liquid crystal compound
(B-2) a compound having a carbon-carbon unsaturated bond and an active hydrogen-reactive group
(C) a photopolymerization initiator
&Lt; 4 > A step of polymerizing the polymerizable liquid crystal compound contained in the second coating film formed by < 3 &gt;. An optical film obtained by the manufacturing method according to claim 36. A polarizing plate comprising the optical film according to any one of claims 28 to 35 and 37. A flat panel display device comprising the optical film according to any one of claims 28 to 35 and 37.

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