KR20130086168A - Composition and optical film - Google Patents

Abstract

PURPOSE: A composition and optical film are provided to be excellent in adhesion between polarizing film and optical film by using compounds with a reacting group comprising a carbon-carbon unsaturated bond and a hydrogen activating group. CONSTITUTION: A composition comprises a polymerizable liquid crystal compound, a compound and a photopolymerization initiator. The compound comprises a carbon-carbon unsaturated bond and a hydrogen activating group. The compound is a compound comprising an isocyanato group as a hydrogen reacting group. The comound is expressed as equation (X).

Description

Compositions and Optical Films {COMPOSITION AND OPTICAL FILM}

The present invention relates to compositions and optical films.

Members including optical films such as polarizing plates and retardation films are used for flat panel display devices (FPDs). As an optical film, what was manufactured by apply | coating the composition containing a polymeric liquid crystal compound, a photoinitiator, and a solvent on a base material is known. For example, Patent Document 1 describes an optical film formed by coating a composition on a substrate subjected to an alignment treatment to obtain a coating film, orienting the polymerizable liquid crystal compound contained in the coating film, and then polymerizing the polymerizable liquid crystal compound. .

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

The present invention includes the following inventions.

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

(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. Two R ^{2 '} in each repeating unit is a group represented by -NH- on one side and-[NC (= O) -R ^3' ]-on the other side. R ^{3 '} represents a group having a hydroxyl group or a carbon-carbon unsaturated bond.

In 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 formula (A).

[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 the C6-C12 monovalent aromatic heterocyclic group which may have a substituent, or may have a C6-C12 monovalent aromatic hydrocarbon group.

Q ³ and Q ⁴ each independently represent a hydrogen atom or a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, or a monovalent having 6 to 20 carbon atoms which may have a substituent. Aromatic hydrocarbon group, halogen atom, cyano group, nitro group, -NR ² R ³ or -SR ² , or Q ³ and Q ⁴ are bonded to each other, and aromatic ring or aromatic heterocyclic ring together with the carbon atom to which they are respectively bonded To form. 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 described above. The methine group which comprises a group may be substituted by the 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). The composition as described in [4] whose L <^1> of Formula (A) is 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 ) _l -E ^2- (A2)

[In Formula (A1) and Formula (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, a sulfur atom, or -NH. It may be substituted by-and the methine group which comprises the said alicyclic hydrocarbon group may be substituted by the tertiary nitrogen atom.

k and 1 respectively independently represent the integer of 0-3. When k is an integer of 2 or more, the plurality of B ¹ may be the same as or different from each other, and the plurality of A ¹ may be the same or different from each other. When l is an integer of 2 or more, the plurality of B ² may be the same as or different from each other, and the plurality of A ² may be the same or different from each other.

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 described above.]

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

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

(1) Process of apply | coating the composition as described in any one of [1]-[5] on a base material;

(2) Process of forming an optical film by polymerizing the polymerizable liquid crystal compound contained in the coating film apply | coated on the base material 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 method 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 of a photo-alignment polymer on its surface.

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

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

[13] The optical film according to [6] or [12], having retardation.

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

[15] A flat panel display device comprising the optical film as described in [6], [12], or [13].

[16] A composition comprising the following (D) and (B).

(D) photo-oriented polymer

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

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

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

[19] The composition as described in [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. Two R ^{2 '} in each repeating unit is a group represented by -NH- on one side and-[NC (= O) -R ^3' ]-on the other side. R ^{3 '} represents a group having a hydroxyl group or a carbon-carbon unsaturated bond.

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

[20] An optical film formed by crosslinking an optical orientation polymer included in the composition according to any one of [16] to [19].

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

(1) Process of apply | coating the composition as described in any one of [16]-[19] on a base material;

(2) Process of forming an optical film by crosslinking the photo-alignment polymer contained in the coating film apply | coated on the base material by (1)

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

[23] The method for producing 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 according to any one of [21] to [23].

[25] A phase difference plate formed by further forming an optically anisotropic layer on the optical film as described in [20] or [24].

[26] A polarizing plate comprising the optical film described in [20] or [24].

[27] A flat panel display device comprising the optical film as described in [20] or [24].

[28] An optical film obtained by laminating 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) contains the following (A), (B-2) and (C).

(D) photo-oriented polymer

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

(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 [28], wherein (D) is a photo-alignment polymer capable of forming a crosslinked structure by light irradiation.

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

[31] The optical film according to [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. Two R ^{2 '} in each repeating unit is a group represented by -NH- on one side and-[NC (= O) -R ^3' ]-on the other side. R ^{3 '} represents a group having a hydroxyl group or a carbon-carbon unsaturated bond.

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

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

[33] The optical film according to 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 according to any one of [28] to [34], having retardation.

[36] A method for producing an optical film, which includes the following steps <1> to <4>.

Process of forming a 1st coating film on a base material by apply | coating the composition (A) containing <1> or less (D) and (B-1) on a base material;

(D) photo-oriented polymer

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

<2> Step of converting 1st coating film into A layer by crosslinking (D) contained in the 1st coating film apply | coated on the base material by <1>;

<2> Forming a 2nd coating film on A layer by apply | coating the composition (B) containing the following (A), (B-2), and (C) on A layer formed by <2>. fair;

(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

<4> A step of polymerizing the polymerizable liquid crystal compound contained in the 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].

BRIEF DESCRIPTION OF THE DRAWINGS It is a cross-sectional schematic diagram which shows an example of the polarizing plate which concerns on this 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 sectional view showing an example of the organic EL display device according to the present invention.

I. First Embodiment of the Invention

1. First composition of the present invention (hereinafter, the first composition of the present invention is sometimes referred to as "this composition (1)", and the optical film manufactured from this composition (1) is sometimes referred to as "this optical film ( 1)

The present composition (1) is a polymerizable liquid crystal compound (A), a compound having a carbon-carbon unsaturated bond and an active hydrogen reactive group in the molecule (hereinafter sometimes referred to as "compound (B)") and (C) It contains a photoinitiator.

1-1. The compound (B)

Compound (B) has a carbon-carbon unsaturated bond and an active hydrogen reactive group in its molecule. An "active hydrogen reactive group" means a group having reactivity with a group having active hydrogen such as carboxyl group (-COOH), hydroxyl group (-OH), amino group (-NH ₂ ), and glycidyl group, oxazoline group, car A bodyimide group, an aziridine group, an imide group, an isocyanato group, a thiisocyanato group, a maleic anhydride group, etc. are mentioned. The number of carbon-carbon unsaturated bonds and active hydrogen reactive groups possessed by the compound (B) is 1-20, preferably 1-10.

It is preferable that compound (B) has at least two active hydrogen reactive groups. Plural active hydrogen reactive groups may be the same or different.

Although the carbon-carbon unsaturated bond which a compound (B) has may be a carbon-carbon double bond, a carbon-carbon triple bond, or a combination thereof, it is preferable if it is a carbon-carbon double bond. Especially, a vinyl group and / or a (meth) acryl group are preferable. Moreover, it is preferable that active hydrogen reactive group is at least 1 sort (s) chosen from the group which consists of an epoxy group, a glycidyl group, and an isocyanato group, and the compound (B) which has an acryl group and an isocyanato group is especially preferable.

As a specific example of a compound (B), The compound which has (meth) acryl group and epoxy groups, such as methacryloxy glycidyl ether and acryloxy glycidyl ether; Compounds having a (meth) acryl group and an oxetane group such as oxetane acrylate and oxetane methacrylate; Compounds having a (meth) acryl group and a lactone group such as lactone acrylate and lactone methacrylate; Compounds having a vinyl group and an oxazoline group such as vinyl oxazoline and isopropenyl oxazoline; Oligomers of compounds having (meth) acrylic groups and isocyanato groups, such as isocyanatomethyl acrylate, isocyanatomethyl methacrylate, 2-isocyanatoethyl acrylate, and 2-isocyanatoethyl methacrylate Can be mentioned. Moreover, the compound etc. which have vinyl groups, vinylene groups, and acid anhydrides, such as methacrylic anhydride, acrylic anhydride, maleic anhydride, and vinyl maleic anhydride, are mentioned. Above all, methacryloxyglycidyl ether, acryloxyglycidyl ether, isocyanatomethyl acrylate, isocyanatomethyl methacrylate, vinyl oxazoline, 2-isocyanatoethyl acrylate, 2-isocia Natoethyl methacrylate and oligomers are preferred, with isocyanatomethyl acrylate, 2-isocyanatoethyl acrylate and oligomers being particularly preferred.

Preferable compound (B) is represented by 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. Two R ^{2 '} in each repeating unit is a group represented by -NH- on one side and-[NC (= O) -R ^3' ]-on the other side. R ^{3 '} represents a group having a hydroxyl group or a carbon-carbon unsaturated bond.

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

Among the compounds (B) represented by formula (X), compounds represented by the following formula (XX) (hereinafter sometimes referred to as "compound (XX)") are particularly preferable (wherein n is the same meaning as described above). being).

Compound (XX) can also be refine | purified and used for commercially available products readily available on the market as it is or as needed. As a commercial item, Laromer (trademark) LR-9000 (made by BASF Corporation) etc. are mentioned, for example.

0.01-10 mass% is preferable with respect to the gross mass of this composition (1), and, as for content of the compound (B) in this composition (1), 0.1-5 mass% is more preferable.

1-2. Polymerizable Liquid Crystal Compound

A polymeric liquid crystal compound is a compound which has a polymeric group and shows a liquid crystal state. A polymerizable group means group which participates in the polymerization reaction of a polymeric liquid crystal compound.

One suitable example of the polymerizable liquid crystal compound is, for example, a compound represented by formula (A) (hereinafter sometimes referred to as "compound (A)").

[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 the C6-C12 monovalent aromatic heterocyclic group which may have a substituent, or may have a C6-C12 monovalent aromatic hydrocarbon group.

Q ³ and Q ⁴ each independently represent a hydrogen atom or a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, or a monovalent having 6 to 20 carbon atoms which may have a substituent. Aromatic hydrocarbon group, halogen atom, cyano group, nitro group, -NR ² R ³ or -SR ² , or Q ³ and Q ⁴ are bonded to each other, and aromatic ring or aromatic heterocyclic ring together with the carbon atom to which they are respectively bonded To form. 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 which comprises a group may be substituted by the 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 methyl group, ethyl group, propyl group, isopropyl group, butyl group and sec-butyl group. Especially, a C1-C3 alkyl group is preferable, a methyl group and an ethyl group are more preferable, and a methyl group is especially preferable.

As an aromatic hydrocarbon group represented by Y <^1> , Monocyclic aromatic hydrocarbon groups, 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 preferably phenyl group and a naphthyl group, and phenyl group it is more preferable.

As an aromatic heterocyclic group represented by Y <^1> , Monocyclic aromatic heterocyclic groups, such as a furyl group, a pyrrolyl group, thienyl group, a pyridinyl group, and a thiazolyl group; Aromatics 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 a benzothiazolyl group, a benzofuryl group and a benzothienyl group Heterocyclic group is mentioned. 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, referred to as "substituent Z ¹ "). Examples of the substituent Z ¹ include 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, and a fluoro having 1 to 6 carbon atoms. Alkyl group, C1-C6 alkoxy group, C1-C6 alkylsulfanyl group, C1-C6 N-alkylamino group, C2-C12 N, N-dialkylamino group, C1-C6 N-alkyl Sulfamoyl group and C2-C12 N, N- dialkyl sulfamoyl group, etc. are mentioned.

In the substituent Z ¹ , a halogen atom includes 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 . Especially, a methyl group and an ethyl group are more preferable, and a methyl group is especially preferable.

In the substituent Z ¹ , as the alkylsulfinyl group, methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl and pentylsulfinyl And a hexyl sulfinyl 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 , as the alkylsulfonyl group, methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, isopropylsulfonyl group, butylsulfonyl group, isobutylsulfonyl group, sec-butylsulfonyl group, tert-butylsulfonyl group and pentylsulfonyl group And a hexylsulfonyl group. Especially, a C1-C4 alkylsulfonyl group is preferable, a C1-C2 alkylsulfonyl group is more preferable, and a methylsulfonyl group is especially preferable.

Examples of the fluoroalkyl group in the substituent Z ¹ include fluoromethyl group, trifluoromethyl group, fluoroethyl group, pentafluoroethyl group, heptafluoropropyl group, and nonafluorobutyl group. Especially, a C1-C4 fluoroalkyl group is preferable, A C1-C2 fluoroalkyl group is more preferable, A trifluoromethyl group is especially preferable.

Examples of the alkoxy group in the substituent Z ¹ include a methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group and hexyloxy group. Can be. Especially, a C1-C4 alkoxy group is preferable, a C1-C2 alkoxy group is more preferable, and a methoxy group is especially preferable.

In the substituent Z ¹ , as the alkylsulfanyl group, methylsulfanyl group, ethylsulfanyl group, propylsulfanyl group, isopropylsulfanyl group, butylsulfanyl group, isobutylsulfanyl group, sec-butylsulfanyl group, tert-butylsulfanyl group, pentylsulfanyl group And a hexylsulfanyl group. Especially, a C1-C4 alkylsulfanyl group is preferable, a C1-C2 alkylsulfanyl group is more preferable, and a methylsulfanyl group is especially preferable.

In the substituent Z ¹ , examples of the N-alkylamino group include N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-sec-butylamino group and N -tert- butylamino group, N-pentylamino group, N-hexylamino group, etc. are mentioned. Especially, a C1-C4 N-alkylamino group is preferable, A C1-C2 N-alkylamino group is more preferable, A N-methylamino group is especially preferable.

As the N, N-dialkylamino group in the substituent Z ¹ , N, N-dimethylamino group, N-methyl-N-ethylamino group, N, N-diethylamino group, N, N-dipropylamino group, N, N-di Isopropylamino group, N, N-dibutylamino group, N, N-diisobutylamino group, N, N-dipentylamino group, N, N-dihexylamino group, etc. are mentioned. Especially, a C2-C8 N, N-dialkylamino group is preferable, A C2-C4 N, N-dialkylamino group is more preferable, A N, N-dimethylamino group is especially preferable.

In the substituent Z ¹ , examples of the N-alkylsulfamoyl group are N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group and N- Isobutyl sulfamoyl group, N-sec-butyl sulfamoyl group, N-tert-butyl sulfamoyl group, N-pentyl sulfamoyl group, N-hexyl sulfamoyl group, etc. are mentioned. Especially, a C1-C4 N-alkylsulfamoyl group is preferable, A C1-C2 N-alkylsulfamoyl group is more preferable, A N-methylsulfamoyl group is especially preferable.

In the substituent Z ¹ , examples of the N, N-dialkylsulfamoyl group include N, N-dimethylsulfamoyl group, N-methyl-N-ethylsulfamoyl group, N, N-diethylsulfamoyl group, and N, N- Dipropylsulfamoyl group, N, N-diisopropylsulfamoyl group, N, N-dibutylsulfamoyl group, N, N-diisobutylsulfamoyl group, N, N-dipentylsulfamoyl group and N, N -Dihexyl sulfamoyl group etc. are mentioned. Especially, a C2-C8 N, N- dialkyl sulfamoyl group is preferable, A C2-C4 N, N- dialkyl sulfamoyl group is more preferable, A N, N- dimethyl sulfamoyl group is especially preferable. Do.

Among them, the substituent Z ¹ is a halogen atom, an alkyl group of 1 to 2 carbon atoms, a cyano group, a nitro group, an alkyl group having a carbon number of 1 to 2 to 1 to 2 carbon atoms of the alkylsulfonyl group, 1 to 2 carbon atoms of the fluoroalkyl alkoxy group, carbon atoms Alkyl sulfanyl groups of 1 to 2, N-alkylamino groups of 1 to 2 carbon atoms, N, N-dialkylamino groups of 2 to 4 carbon atoms, and alkyl sulfamoyl groups of 1 to 2 carbon atoms are preferable, and halogen atoms, methyl groups, and Especially preferred are no group, nitro group, sulfo group, carboxyl group, trifluoromethyl group, methoxy group, methylsulfanyl group, N, N-dimethylamino group and N-methylamino group.

When Y ¹ may be 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), respectively. Can be.

[In Formulas (Y-1) to (Y-6),

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

a1 is an integer of 0-5, a2 is an integer of 0-4, b1 is an integer of 0-3, b2 represents an integer of 0-2, 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 from each other.]

Y <^1> is especially preferable at the point which can manufacture a compound (A) easily, and a cost, as long as it is group represented by a formula (Y-1) or a 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 are represented by formulas (Y ¹ -1) to (Y ¹ -7), respectively. The group can be mentioned.

[Equation (Y ¹ -1) to (Y ¹ -7),

* Represents a bond 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 hetero atom such as S, N, O or Se or a group containing this hetero atom.

a represents an integer of 0 to 3;

b represents the integer of 0-2.

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 from each other.]

Each of V ¹ and V ² is preferably -S-, -NR ^9- , or -O-, and each of W ^{1 to} W ⁵ is preferably -CH = or -N =.

It is preferable that a is 0 or 1, and it is preferable that b is 0.

In addition, even if the Y ¹ have a substituent polycyclic aromatic hydrocarbon group, or even if they have a substituent other words in the case of good polycyclic aromatic heterocyclic group, formula (Y ² -1) ~ group represented by the formula (Y ² -6) It is more preferable.

In the formula (Y ² -1) ~ formula (Y ² -6),

*, Z ¹ , a, b, V ¹ , V ² and W ¹ represent the same meaning as described above.]

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

Examples of the aliphatic hydrocarbon group represented by Q ³ and Q ⁴ include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, 1-methylbutyl group, 3 -Methylbutyl group, hexyl group, 1-methylpentyl group, 4-methylpentyl group, heptyl group, 1-methylhexyl group, 5-methylhexyl group, octyl group, 1-methylheptyl group, nonyl group, 1-methyl Octyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group and eicosyl group. Alkyl groups having 1 to 12 carbon atoms are preferred, and methyl and ethyl groups are particularly preferred.

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, a cyclodecyl group, and the like. Preference is given to cyclic alkyl groups having 3 to 12 carbon atoms.

As an aromatic hydrocarbon group represented by Q <^3> and Q <^4> , a phenyl group, a biphenyl group, 1-naphthyl group, 2-naphthyl group, 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group, etc. are mentioned, A C6-C14 aromatic hydrocarbon group 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 ¹ .

R <^2> and R <^3> is a C1-C6 alkyl group, Especially, a C1-C4 alkyl group is preferable, A methyl group and an ethyl group are more preferable, A methyl group is especially preferable.

Q ³ and Q ⁴ may be bonded to each other to form an aromatic ring or an aromatic heterocycle. As a ring which Q <^3> and Q <^4> form, an aromatic heterocycle is preferable, For example, Formula (Q ') in a compound (A)

It is more preferable if the partial structure represented by the structure is represented by the formula (Q).

In the formula (Q),

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

Specific examples of the combinations of X ¹ , Y ¹ , Q ³ and Q ⁴ in Formula (A)

When represented by the partial structure shown by the following, what is chosen from the group which consists of the following formula (ar-1)-formula (ar-135) is mentioned.

Among the partial structures represented by the formula (ar), the compound (A) containing the structure represented by the formula (ar-86) is easier to produce the compound (A) itself and includes a compound (A). Since it is easy to control the wavelength dispersion of the phase difference of the optical film formed from a composition, it is preferable.

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 — or -NR ⁴ -CO- is preferred, more preferably * -OC (= O)-, * -OC (= S)-, * -O-CR ⁴ R ^5- , * -NR ⁴ -CR ⁵ R ^6- or * -NR ⁴ -CO-, more preferably * -OC (= O)-, * -OC (= S)-or * -NR ⁴ -CO-(* is represented by the formula (ar) The number of bonds with the benzene ring to which Q ¹ and Q ² are bonded 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, and 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 temporary exchange hydrocarbon group, and a 5- or 6-membered ring is preferable. Although this alicyclic hydrocarbon group may be saturated or unsaturated, saturated alicyclic hydrocarbon group is preferable. In addition, the alicyclic hydrocarbon group represented by G ¹ and G ² is a case where -CH ₂ -constituting it is substituted with -O-, -S- or -NH-, or the methine constituting it is substituted with a tertiary nitrogen atom. In some cases. That is, G ¹ and G ² may be a group containing a hetero atom. Specific examples of G ¹ and G ² are represented by formulas (g-1) to (g-10), respectively.

Hydrogen atoms contained groups divalent alicyclic hydrocarbon group represented by G ¹ and G ² are good even if they are substituted with a substituent (referred to as "the substituent Z ^2" in some cases hereinafter). Examples of the substituent Z ² include alkyl groups having 1 to 4 carbon atoms such as methyl group, ethyl group, isopropyl group and tert-butyl group; C1-C4 alkoxy groups, such as a methoxy group and an ethoxy group; Fluoroalkyl groups having 1 to 4 carbon atoms such as trifluoromethyl group; Fluoroalkoxy groups having 1 to 4 carbon atoms such as trifluoromethoxy group; Cyano; A nitro group; Halogen atoms, such as a fluorine atom, a chlorine atom, and a bromine atom, are mentioned.

As G <^1> and G <^2>, it is preferable that they are a bivalent alicyclic hydrocarbon group represented by Formula (g-1). Especially, it is more preferable that G <^1> and G <^2> are a cyclohexane- 1, 4- diyl group, and it is especially preferable that they are 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 referred to as "group (A1)" in some cases), and L ² is a group represented by formula (A2) (hereinafter, in some cases) "Group A2").

P ¹ -F ^1- (B ¹ -A ¹ ) _k -E ^1- (A1)

P ² -F ^2- (B ² -A ² ) _l -E ^2- (A2)

[In Formula (A1) and Formula (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, a sulfur atom, or -NH. It may be substituted by-and the methine group which comprises the said alicyclic hydrocarbon group may be substituted by the tertiary nitrogen atom.

k and 1 respectively independently represent the integer of 0-3. When k is an integer of 2 or more, the plurality of B ¹ may be the same as or different from each other, and the plurality of A ¹ may be the same or different from each other. When l is an integer of 2 or more, the plurality of B ² may be the same as or different from each other, and the plurality of A ² may be the same or different from each other.

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 meaning as described above.]

Specific examples of the divalent alicyclic hydrocarbon group represented by A ¹ and A ² in the groups (A1) and (A2) are exemplified as divalent alicyclic hydrocarbon groups of G ¹ and G ² , and a suitable example thereof is also illustrated. As a suitable example of G ¹ and G ² . The divalent aromatic hydrocarbon group represented by A ¹ and A ² may be monocyclic or polycyclic (including polycyclic and condensed polycyclic 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), for example. Moreover, as aromatic hydrocarbon group represented by A <^1> and A <^2> , group which has a symmetry axis or a symmetry plane is preferable.

The hydrogen atom contained in the alicyclic hydrocarbon group and aromatic hydrocarbon group represented by A <^1> and A <^2> may be substituted by the substituent. Examples of the substituent include those exemplified as the substituent Z ² which may optionally have an alicyclic hydrocarbon group represented by G ¹ or G ² .

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

B ¹ and B ^2, so tend to facilitate the production of the compound (A) is preferably the same type of group. 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} - is a bond or, however, is preferable because it tends to be more easily producing a compound (a). In that it easy to form the optical film with a high liquid crystal B ² between the two B ¹ A, 2 A ^2, between ¹ is preferably with -C (= O) -O-.

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

It is preferable that k and l respectively independently represent the integer of 0-3, and it is more preferable that k and l are 0-2. As for the sum total of k and l, 4 or less are more preferable. When k and l are the said ranges, there exists a tendency for a compound (A) to show liquid crystallinity more easily.

It is preferable that F <^1> and F <^2> are a C1-C12 alkanediyl group each independently, and it is more preferable that it is a linear alkanediyl group. In particular, an unsubstituted alkanediyl group is preferable. The hydrogen atom contained in the said alkanediyl group may be substituted by the C1-C5 alkoxy group or halogen atom. In addition, -CH ₂ -constituting the alkanediyl group may be substituted with -O- or -C (= O)-.

P ¹ and P ² are hydrogen atoms or polymerizable groups, and at least one is a polymerizable group. When it is going to obtain this optical film which is excellent in hardness, it is preferable that P <^1> and P <^2> are a polymerizable group together.

A polymerizable group means the characteristic group which can superpose | polymerize a compound (A), Specifically, a vinyl group, vinyloxy group, styryl group, p- (2-phenylethenyl) phenyl group, acryloyl group, methacryloyl group Polymerizable groups having ethylenically unsaturated groups such as acryloyloxy group and methacryloyloxy group; Carboxyl groups; Acetyl group; A hydroxy group; Carbamoyl group; An alkylamino group having 1 to 4 carbon atoms; An amino group; Oxiranyl group; An oxetanyl group, a formyl group, an isocyanato group, an isothiocyanato group, etc. are illustrated.

As the polymerizable group, a radically polymerizable group and a cationically polymerizable group suitable for photopolymerizing the compound (A) are preferable, and acryloyl group, methacryloyl group, acryloyloxy group and methacryloyloxy group are particularly preferable. Especially, it is preferable that a polymeric group is an acryloyloxy group or a methacryloyloxy group each independently, and it is especially preferable that it is acryloyloxy group.

In consideration of the ease of preparation of the compound (A), the group (A1) and the group (A2) are preferably the same, that is, the same as L ¹ and L ² .

Similarly, in compound (A), D ¹ and D ² are the same, and G ¹ and G ² are the same, that is, the group represented by -D ¹ -G ¹ -L ¹ and -D in compound (A) ^It is preferable that the groups represented by ² -G ² -L ² are the same. In this case, compound (A) can be manufactured more easily.

A specific example of -D ¹ -G ¹ -L ¹ when L ¹ is a group represented by formula (A1) and a sphere of -D ² -G ² -L ² when L ² is a group represented by formula (A2) Examples include groups represented by the following formulas (R-1) to (R-134).

On the other hand, n in formula (R-1)-(R-134) represents the integer of 2-12, Preferably it is 3-10, More preferably, it is 4-8.

It is preferable that the compound (A) in which L ¹ is a group (A1) and L ² is a group (A2) also satisfies the relationship between the formulas (1) and (2) together.

(N _π -4) / 3 <k + l + 4 (1)

12≤N _π ≤22 (2)

In the equation (1) and (2) of, N _π is formula (A) according ^{to, -D 1 -G 1 -L 1,} -D 2 -G 2 include an aromatic ring having a portion other than a -L ² The number of pi electrons to be represented. k and l represent the same meaning as described 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, the compound (A) is referred to as "compound (xvi)" according to the number in the table) has a partial structure represented by the formula (ar). The group represented by formula (ar-39), and groups represented by -D ¹ -G ¹ -L ¹ are represented by (R-1) to (R-48), (R-56) to (R-120), and ( R-129) to (R-131), a group selected from the group consisting of -D ² -G ² -L ² is represented by (R-1) to (R-48) and (R-56) to It means a compound selected from the group consisting of (R-131).

For example, compound (xvi) is a structure in which the partial structure represented by formula (ar) is represented by formula (ar-39), and groups represented by -D ¹ -G ¹ -L ¹ are represented by (R-1) to (R -48), (R-56) to (R-120) and (R-129) to (R-131) is a group selected from the group represented by -D ² -G ² -L ² ( 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 The group represented by -L ¹ is a group selected from the group consisting of (R-1) to (R-48), (R-56) to (R-120), and (R-129) to (R-131). , A mixture with a compound represented by -D ² -G ² -L ² is a group selected from the group consisting of (R-1) to (R-48) and (R-56) to (R-131), ie Compound (xvi) means a mixture of two compounds (A).

As a specific example of the compound (A) of a table | surface, the following compounds are mentioned, for example. Among the compounds (A) shown in the table, compound (i), compound (iii), compound (iv), compound (v), compound (viii), compound (ix), compound (x), compound (xv) and compound Representative structural formulas of (xvii), compound (xviii), compound (xix), compound (xx), compound (xxii), compound (xxiii), compound (xxiv) and compound (xxv) are illustrated. The following chemical formulas shall include all stereoisomers. In addition, it is preferable that all the cyclohexane- 1, 4- diyl groups of compound (i)-compound (xxv) are trans-cyclohexane- 1, 4- diyl groups.

Moreover, as a compound (A), what is respectively represented by Formula (A1)-a formula (A61) is mentioned.

(The two * in formula (A1) are combined with any one of (A1-1) to (A1-8).)

(The two * in formula (A2) are combined with any one of (A2-1) to (A2-8).)

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

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

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

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

(The two * in formula (A7) are combined with any one of (A7-1) to (A7-8).)

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

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

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

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

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

(The two * in formula (A13) are combined with any one of (A13-1) to (A13-8).)

(The two * in formula (A14) are combined with any one of (A14-1) to (A14-8).)

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

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

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

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

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

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

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

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

(The two * in formula (A23) are combined with any one of (A23-1) to (A23-8).)

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

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

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

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

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

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

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

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

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

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

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

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

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

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

(Two * in formula (A38) are combined with any one of (A38-1) to (A38-8))

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

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

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

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

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

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

(The two * in formula (A45) are combined with any one of (A45-1) to (A45-8).)

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

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

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

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

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

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

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

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

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

(The two * in formula (A55) are combined with any one of (A55-1) to (A55-8).)

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

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

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

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

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

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

In addition, the following can also be used as a compound (A).

Compound (A) has been described in Methoden der Organischen Chemie, Organic Reactions, Organic Syntheses, Comprehensive Organic Synthesis, New Experimental Chemistry Lectures, etc. By suitably combining the benzylation reaction, Sonogashira reaction, Suzuki-Miyaura reaction, Negishi reaction, Kumada reaction, Hiyama reaction, Buchwald-Hartwig reaction, Friedel-Crafts reaction, Heck reaction, Aldol reaction, etc. according to the structure, It can manufacture.

Compound (A) in the case where D ¹ and D ² are * -O-CO- will be described as an example for the preparation method thereof. First, a compound (compound (1-1)) represented by formula (1-1) and a compound (compound (1-2)) represented by formula (1-2) are prepared, respectively, to give compound (1-1) and By reacting compound (1-2), a compound (compound (1-3)) represented by formula (1-3) is obtained.

[Wherein X ¹ , Y ¹ , Q ¹ and Q ² represent the same meaning as in formula (A).]

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

[Wherein 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 meaning as above.]

Subsequently, compound (A) can be manufactured by making compound (1-3) and compound (1-4) represented by Formula (1-4) react.

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

It is preferable to perform reaction of compound (1-1) and compound (1-2), and reaction of compound (1-3) and compound (1-4) in presence of an esterification agent.

As esterification agent (condensing agent), 1-cyclohexyl-3- (2-morpholinoethyl) carbodiimide met-para-toluenesulfonate, dicyclohexyl carbodiimide, 1-ethyl-3- (3-dimethyl Aminopropyl) carbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (some water soluble carbodiimides are 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- (4-nitrobenzenesul Ponyl) -1H-1,2,4-triazole, 1H-benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate, 1H-benzotriazol-1-yloxytris (dimethylamino) force Phosphorus hexafluorophosphate, N, N, N ', N'-tetramethyl-O- (N-succinimidyl) uroniumtetrafluoroborate, N- (1,2,2,2-tetrachloroethoxy Carbonyloxy) succinimide, N-carbobenzoxoxysuccinimide, O- (6-chlorobenzotriazol-1-yl) -N, N, N ', N'-tetramethyluroniumtetrafluoro Borate, O- (6-chlorobenzotriazol-1-yl) -N, N, N ', N'-tetramethyluronium hexafluorophosphate, 2-bromo-1-ethylpyridiniumtetrafluoroborate , 2-chloro-1,3-dimethylimidazolinium chloride, 2-chloro-1,3-dimethylimidazolinium Tetrafluorophosphate, 2-chloro-1-methylpyridinium iodide, 2-chloro-1-methylpyridinium para-toluenesulfonate, 2-fluoro-1-methylpyridinium para-toluenesulfonate, triclo Rotate acetate pentachlorophenyl ester etc. are mentioned. Among them, dicyclohexylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, 1-ethyl-3- (3) as a condensing agent can be used since the reactivity, cost, and a wide range of solvents can be used. -Dimethylaminopropyl) carbodiimide hydrochloride, bis (2,6-diisopropylphenyl) carbodiimide, bis (trimethylsilyl) carbodiimide, bisisopropylcarbodiimide, 2,2'-carbonylbis- 1H-imidazole is preferred.

When this composition (1) contains a compound (A) as a polymeric liquid crystal compound, the content is represented by the content rate with respect to solid content of this composition (1), 10-99.9 mass% is preferable, and 20-99 mass % Is more preferable, 50-97 mass% is more preferable, 80-95 mass% is especially preferable. If content of a compound (A) is the said range, the same polarization conversion will be possible in the wide wavelength range of the optical film 1 obtained. Solid content means the total amount of the component except low-volatile components, such as a solvent, in this composition (1). In this composition (1), a compound (A) may be used independently and may use 2 or more types of compound (A) together, as shown with the compound (xvi) of a table | surface.

As a polymerizable liquid crystal compound, "3.8.6 network (complete crosslinking type)" of a liquid crystal handbook (Liquid Crystal Handbook Editing Committee edition, issued March 30, 2000), "6.5.1 liquid crystal material b. A compound having a polymerizable group among the compounds described in "Polymerizable nematic liquid crystal material", Japanese Patent Application Laid-Open No. 2010-31223, Japanese Patent Application Laid-Open No. 2010-270108, Japanese Patent Application Laid-Open No. 2011-6360, and Japanese Patent Publication No. 2011-207765 The polymeric liquid crystal compound of Unexamined-Japanese-Patents is mentioned.

As a polymeric liquid crystal compound, the compound represented by Formula (3) (henceforth called "compound (3)") etc. are mentioned, for example.

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

[Equation (3),

A ¹¹ represents an aromatic heterocyclic ring 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 are each independently -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-O-CR ^{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> -R <^16> represents a hydrogen atom or a C1-C4 alkyl group.

G is a hydrogen atom, a halogen atom, a C1-C13 alkyl group, a C1-C13 alkoxy group, a C1-C13 fluoroalkyl group, a C1-C13 N-alkylamino group, a cyano group, a nitro group, or -E ^12- P ¹² is represented.

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

P ¹¹ and P ¹² represent a polymerizable group.

t represents the integer of 1-5. When t is an integer of 2 or more, the plurality of B ¹¹ may be the same as or different from each other, and the plurality of A ¹¹ may be the same or different from each other.]

Examples of the aromatic hydrocarbon ring represented by A ¹¹ include a benzene ring, a naphthalene ring, an anthracene ring and a phenanthroline ring, and 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. Etc. can be mentioned. Especially, a benzene ring, a thiazole ring, and a benzothiazole ring are preferable. As an aromatic hydrocarbon ring or aromatic heterocycle represented by A <^11> , the bivalent group represented, respectively, by a formula (Ara-1)-a formula (Ara-11) is mentioned, for example.

[Formula (Ara-1) to Formula (Ara-11),

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

Y <^3> represents the same thing as group illustrated as Y <^1> in Formula (A).

Z <^3> represents the same thing as group illustrated 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 the integer of 0-6.

n represents the integer of 0-4.

o represents the integer of 0-2.

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

As an aromatic hydrocarbon ring or aromatic heterocycle represented by A <^11> , group represented by a formula (Ara-1) and a formula (Ara-7), respectively, is preferable, and the following group is specifically illustrated.

Carbon number of the alicyclic hydrocarbon group represented by A <^11> is 3-18, for example, it is preferable that it is 5-12, and it is especially preferable that it is 5 or 6. Examples of the alicyclic hydrocarbon group represented by A ¹¹ include a cyclohexane-1,4-diyl group. Examples of the substituent which the alicyclic hydrocarbon group may have include a halogen atom and an alkyl group having 1 to 6 carbon atoms which may have a fluoro group, and an alkoxy group having 1 to 6 carbon atoms, a nitro group and a cyano group which may have a fluoro group.

Examples of the polymerizable group represented by P ¹¹ and P ¹² include the same groups as those exemplified as the polymerizable group represented by P ¹ and P ² of the compound (A). Since it can superpose | polymerize (curable) at low temperature, a photopolymerizable group is preferable, A radically polymerizable group or a cationically polymerizable group is more preferable, Especially handling is easy and since manufacture of compound (3) is easy, P ¹¹ And the polymerizable group represented by P ¹² is preferably a group represented by formulas (P-1) to (P-5), respectively.

[In 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 is an alkanediyl group of 1 to 18 carbon atoms, straight-chain or is an alkanediyl group having 1 to 12 carbon atoms preferably where the one branch point.

As compound (3), the following are mentioned, for example.

When this composition (1) contains compound (3) and / or compound (A) as a polymeric liquid crystal compound, the content is a compound (3) with respect to 100 mass parts of total amounts of a compound (A) and a compound (3), for example. ) 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, this optical film 1 which has desired wavelength dispersion characteristic can be formed by adjusting content of the structural unit derived from a compound (A), and content of the structural unit derived from a compound (3), for example. When this optical film 1 increases content of the structural unit derived from a compound (A), it exists in the tendency to show reverse wavelength dispersion characteristic more. In order to form this optical film 1 which has desired wavelength-dispersion characteristic, about 2-5 types of this composition (1) in which content of the structural unit derived from a compound (A) differs are prepared, and each main composition (1 ), The optical film of the same film thickness is manufactured, and the phase difference value is calculated | required. And the compound which is necessary in order to obtain | require a correlation between content of the structural unit derived from a compound (A), and the phase difference value of an optical film from a result, and to give a desired phase difference value to the optical film in the said film thickness from the obtained correlation ( What is necessary is just to determine content of the structural unit derived from A).

As a polymerizable liquid crystal compound, the compound (henceforth called "compound (X1)") etc. containing the group represented by Formula (X1), etc. are mentioned, for example.

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

(In 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 this bivalent alicyclic hydrocarbon group and bivalent aromatic hydrocarbon group may be substituted by the halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a cyano group, or a nitro group, and the said C1-C6 The hydrogen atom contained in the alkyl group and the said C1-C6 alkoxy group may be substituted by the fluorine atom.

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

B ¹² and B ¹³ are each independently -C≡C-, -CH = CH-, -CH ₂ -CH _2- , -O-, -S-, -C (= O)-, -C (= O ) -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 (= O) -O-, - OC (= O) -CH = CH- or a single bond.

E ¹¹ represents an alkanediyl group having 1 to 12 carbon atoms, hydrogen atoms contained in the alkanediyl group is good even if it is substituted by alkoxy having 1 to 5 carbon atoms, hydrogen atoms included the alkoxy groups are good even if they are substituted with a halogen atom . In addition, -CH ₂ -constituting the alkanediyl group may be substituted with -O- or -CO-.

* Represents the number of bonds)

Carbon number of the aromatic hydrocarbon group and alicyclic hydrocarbon group of A <^11> is 3-18, for example, it is preferable that it is 5-12, and it is especially preferable that it is 5 or 6. As A ^{11, a} cyclohexane-1,4-diyl group and a 1,4-phenylene group are preferable.

E ¹¹ as it is preferred alkanediyl group having 1 to 12 carbon atoms in the straight. -CH ₂ -constituting this alkanediyl group may be substituted with -O-.

Specifically, methylene group, ethylene group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1, 7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group and dodecane-1,12-di C1-C12 linear alkanediyl groups, such as a diary; -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 ₂ -CH ₂ -O-CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -and the like.

The polymerizable group represented by P ¹¹ is preferably a polymerizable radical or a cationic polymerizable group in view of high polymerization reactivity, in particular, photopolymerization reactivity, and is easy to handle. The group represented by the formulas (P-11) to (P-15) is preferable.

In formulas (P-11) to (P-15),

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

If the group represented by formula (P-11)-a formula (P-15) is illustrated more concretely, the group represented by following formula (P-16)-a formula (P-20) is mentioned.

It is preferable that P <^11> is group represented by Formula (P-14)-a formula (P-20), and a vinyl group, a p-stilbene group, an epoxy group, an oxetanyl group, etc. are further more preferable.

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

As compound (X1), the compound represented, for example by Formula (I), Formula (II), Formula (III), Formula (IV), Formula (V), or Formula (VI) is mentioned.

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)

P¹¹-B¹¹-E¹¹-B¹²-A¹¹-B¹³-A¹²-B¹⁴-A¹³-B¹⁵-A¹⁴-F¹¹ (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)

P¹¹-B¹¹-E¹¹-B¹²-A¹¹-B¹³-A¹²-B¹⁴-A¹³-F¹¹ (IV)

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

P¹¹-B¹¹-E¹¹-B¹²-A¹¹-B¹³-A¹²-F¹¹ (VI)

(Wherein,

A ¹² ~A ¹⁴ is A ¹¹ and consent, B ¹⁴ and B ¹² are ~B ¹⁶ and consent, B ¹⁷ and B is ¹¹ and agreed, E ¹² and E ¹¹ are agreed.

F ¹¹ is a hydrogen atom, an alkyl group having 1 to 13 carbon atoms, an alkoxy group having 1 to 13 carbon atoms, a cyano group, a nitro group, a trifluoromethyl group, a dimethylamino group, a hydroxyl 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-)

As a specific example of compound (X1), the following formula (I-1)-a formula (I-4), a formula (II-1)-a formula (II-4), a formula (III-1)-a formula (III-26) are shown, for example. ), The compounds represented by formulas (IV-1) to (IV-19), formulas (V-1) to (V-2), and formulas (VI-1) to (VI-6). Can be mentioned. However, in formula, k1 and k2 represent the integer of 2-12. If these compounds are easy to obtain, such as manufacture of the compound itself or is marketed, it is preferable.

Content of the compound (X1) in this composition (1) is represented by the content rate with respect to solid content of the composition (1), 10-99.9 mass% is preferable, 20-99 mass% is more preferable, 50- 98 mass% is more preferable, and 80-97 mass% is especially preferable. If it is in the said range, at the time of manufacture of this optical film, it can use as a composition excellent in the coating property (coating property) with respect to a base material. Solid content means the total amount of the component except low-volatile components, such as a solvent, in the composition (B).

1-3. Photopolymerization initiator

A photoinitiator is a compound which can generate an active radical by the action of light, and can start superposition | polymerization of a polymeric liquid crystal compound. As a photoinitiator, an alkyl phenone compound, a benzoin compound, a benzophenone compound, an oxime compound, etc. are mentioned.

As an alkyl phenone compound, the (alpha)-aminoalkyl phenone compound, the (alpha)-hydroxyalkyl phenone compound, and the (alpha)-alkoxy alkyl phenone compound are mentioned.

Examples of the α-aminoalkylphenone compound include 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propane-1-one and 2-dimethylamino-1- (4-morpholinophenyl) -2 -Benzylbutan-1-one and 2-dimethylamino-1- (4-morpholinophenyl) -2- (4-methylphenylmethyl) butan-1-one and the like, and preferably 2-methyl- 2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one, 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutan-1-one, etc. are mentioned. have. The α-aminoalkylphenone compound is a commercially available product such as Irgacure® 369, 379EG, 907 (above, manufactured by BASF Japan Co., Ltd.) and Seikeol (registered trademark) BEE (manufactured by Seiko Chemical Co., Ltd.). You may.

As an α-hydroxyalkyl phenone compound, 2-hydroxy-2-methyl-1-phenylpropan-1-one and 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl] And oligomers of propane-1-one, 1-hydroxycyclohexylphenyl ketone, and 2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl] propan-1-one. For the α-hydroxyalkylphenone compound, commercially available products such as Irgacure 184, 2959, 127 (above, manufactured by BASF Japan Co., Ltd.) and Sakeol Z (manufactured by Seiko Chemical Co., Ltd.) may be used.

Examples of the α-alkoxyalkylphenone compound include diethoxy acetophenone, benzyl dimethyl ketal, and the like. You may use commercially available products, such as Irgacure 651 (above, BASF Japan Co., Ltd. product) as an (alpha)-alkoxy alkyl phenone compound.

As an alkylphenone compound, the (alpha)-aminoalkyl phenone compound is preferable and the compound represented by a formula (C-1) is more preferable. By including this compound, there exists a tendency which is excellent in the heat resistance and heat-and-moisture resistance of the optical film obtained.

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

As a benzoin compound, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, etc. are mentioned, for example.

Examples of the benzophenone compounds include benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenylsulfide and 3,3 ', 4,4'-tetra (tert-butylperoxycar Carbonyl) benzophenone, 2, 4, 6-trimethyl benzophenone, etc. are mentioned.

Examples of the oxime compound include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2 -Imines, N-acetoxy-1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] ethane-1-imine and N-acetoxy-1- [9-ethyl -6- {2-methyl-4- (3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy) benzoyl} -9H-carbazol-3-yl] ethane-1-imine, etc. are mentioned. . As an oxime compound, you may use commercially available products, such as Irgacure OXE-01, OXE-02 (above BASF Japan make), and N-1919 (ADEKA make).

A photoinitiator may be used individually by an acetophenone compound, a benzoin compound, a benzophenone compound, an oxime compound, etc., and may use 2 or more types together. Especially, it is preferable to use an acetophenone compound as a photoinitiator. It is preferable that the usage-amount of an acetophenone compound is 90 mass parts or more with respect to a photoinitiator whole quantity, and it is more preferable that the photoinitiator whole quantity is an acetophenone compound.

Content of the photoinitiator in this composition (1) becomes like this. Preferably it is 0.1 mass%-30 mass% with respect to solid content of this composition (1), More preferably, it is 0.5 mass%-10 mass%. If it is in the said range, when superposing | polymerizing the polymeric liquid crystal compound contained in this composition (1), it can suppress more disturbing the orientation of a compound (A). In addition, solid content means the total amount of components except low-volatile components, such as a solvent, in this composition (1).

1-4. Organic solvent

It is preferable that this composition (1) contains a solvent, especially an organic solvent, in order to make operability of optical film manufacture favorable. As an organic solvent, the organic solvent which can melt | dissolve the structural component of this composition (1) is preferable, and also the solvent which is inert to the polymerization reaction of the polymeric liquid crystal compound contained in this composition (1) is more preferable. Specific examples 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, γ-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 aliphatic hydrocarbon solvents such as pentane, hexane and heptane; Non-chlorine aromatic hydrocarbon solvents such as toluene and xylene; Nitrile solvents such as acetonitrile; Ether solvents such as tetrahydrofuran and dimethoxyethane; Chlorine solvents such as chloroform and chlorobenzene; And the like. The organic solvent may be used alone or in combination of two or more thereof. Among them, alcohol solvents, ester solvents, ketone solvents, non-chlorine aliphatic hydrocarbon solvents and non-chlorine aromatic hydrocarbon solvents are preferable. In particular, since the constituent components of the present composition have excellent compatibility and can be dissolved in alcohol solvents, ester solvents, ketone solvents, non-chlorine aliphatic hydrocarbon solvents, chlorine aromatic hydrocarbon solvents, and the like, chlorine solvents such as chloroform may be used. Even if it does not, it can obtain this composition which can apply | coat on a suitable base material and can manufacture this optical film.

When this composition (1) contains the organic solvent, 10 mass parts-10000 mass parts are preferable with respect to 100 mass parts of solid content, More preferably, they are 100 mass parts-5000 mass parts. Moreover, solid content concentration in this composition (1) becomes like this. Preferably it is 2 mass%-50 mass%, More preferably, it is 5-50 mass%. Solid content means the total amount of the component except low-volatile components, such as a solvent, in this composition (1).

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

1-5. Photosensitizer

As a photosensitizer, Xanthones, such as xanthone and thioxanthone; Anthracenes having substituents such as anthracene and alkyl ethers; Phenothiazine; Rubrene.

By using a photosensitizer, superposition | polymerization, such as a polymeric liquid crystal compound, can be highly sensitive. In addition, the usage-amount of a photosensitizer is 0.1 mass part-30 mass parts with respect to 100 mass parts of polymeric liquid crystal compounds, Preferably, they are 0.5 mass part-10 mass parts.

1-6. Leveling agent

Examples of the leveling agent include organic modified silicone oil, polyacrylate, and perfluoroalkyl leveling agents. Specifically, for example, DC3PA, SH7PA, DC11PA, SH28PA, SH29PA, SH30PA, ST80PA, ST86PA, SH8400, SH8700, FZ2123 (above, manufactured by Toray Dow Corning Co., Ltd.), KP321, KP323, KP324, KP326, KP340, KP341 , X22-161A, KF6001 (above, all manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, TSF4460 (above, all Momental Performance Japan Joint Company made), Florina art (fluorinert) (registered trademark) FC-72, copper FC-40, copper FC-43, copper FC-3283 (all manufactured by Sumitomo 3M Co., Ltd.), mega park (registered trademark) R -08, East R-30, East R-90, East F-410, East F-411, East F-443, East F-445, East F-470, East F-477, East F-479, East F -482, copper F-483 (above, all manufactured by DIC Corporation), F-top (brand name) EF301, copper EF303, copper EF351, copper EF352 (all, manufactured by Mitsubishi Material Denshi Chemical Co., Ltd.), sufflon (Registered trademark) S-381, S-382, S-383, S-393, SC-101, SC-105, KH-40, SA-100 AGC Seiko Chemical Co., Ltd.), brand name E1830, copper E5844 (made by Daikin Fine Chemical Co., Ltd.), BM-1000, BM-1100, BYK-352, BYK-353, BYK-361N (all Trade name: BM Chemie Co., Ltd.); A leveling agent may be used independently and may use 2 or more types together.

By using a leveling agent, the optical film obtained can be smoothed more. Moreover, the crosslinking density of the optical film obtained by controlling the fluidity | liquidity of a composition in the manufacturing process of an optical film, or superposing | polymerizing a polymeric liquid crystal compound can be adjusted. Moreover, the usage-amount of a leveling agent is 0.1 mass part-30 mass parts with respect to 100 mass parts of polymeric liquid crystal compounds, Preferably, they are 0.1 mass part-10 mass parts.

1-7. Chiralze

As a chiral agent, a known chiral agent (for example, liquid crystal device handbook, Chapter 3, paragraphs 4-3, chiral agent for TN and STN, p. 199, JPSPS Article 142, 1989) Can be used.

A chiral agent generally contains an asymmetric carbon atom, but a axially asymmetric compound or a surface asymmetric compound that does not contain an asymmetric carbon atom can also be used as the chiral agent. Examples of layered asymmetric compounds or faceted asymmetric compounds include vinaphthyl, helicene, paracyclophane and derivatives thereof.

For example, Japanese Patent Application Laid-Open No. 2007-269640, Japanese Patent Publication No. 2007-269639, Japanese Patent Publication No. 2007-176870, Japanese Patent Publication No. 2003-137887, Japanese Patent Publication No. 2000-515496, Japanese Patent Publication The compound as described in Unexamined-Japanese-Patent No. 9-506088, Unexamined-Japanese-Patent No. 9-506088 is mentioned, Preferably, paliocolor (trademark) LC756 by BASF Japan Corporation is mentioned.

The usage-amount of a chiral agent is 0.1 mass part-30 mass parts with respect to 100 mass parts of polymeric liquid crystal compounds, Preferably, they are 1.0 mass part-25 mass parts. If it is in the said range, when superposing | polymerizing the polymeric liquid crystal compound contained in this composition (1), it can suppress more disturbing the orientation of a polymeric liquid crystal compound.

1-8. Polymerization inhibitor

As a polymerization inhibitor, For example, hydroquinones which have substituents, such as hydroquinone and an alkyl ether; Catechols having substituents such as alkyl ethers such as butyl catechol; Radical complements such as pyrogallols and 2,2,6,6-tetramethyl-1-piperidinyloxyradical; Thiophenols; (beta) -naphthylamine, (beta) -naphthol, etc. are mentioned.

By using a polymerization inhibitor, superposition | polymerization of a polymeric liquid crystal compound can be controlled and stability of the optical film 1 can be improved. Content of a polymerization inhibitor is 0.1 mass part-30 mass parts with respect to 100 mass parts of polymeric liquid crystal compounds, Preferably, they are 0.5 mass part-10 mass parts. If it is in the said range, a polymeric liquid crystal compound can be polymerized without disturbing the orientation of a polymeric liquid crystal compound.

2. optical film

This optical film 1 superposes | polymerizes a polymeric liquid crystal compound. This optical film 1 is a film which can transmit light, and is a film which has an optical function. Optical function means refraction, birefringence, etc.

Among the optical films 1, those having excellent transparency in the visible light region are preferable because they can be used as various display device members. The thickness of this optical film 1 can be suitably adjusted according to the use of this optical film 1, It is preferable that it is 0.1 micrometer-10 micrometers, It is more preferable that it is 0.2 micrometer-5 micrometers in the point which makes photoelasticity small. Do.

When using this optical film 1 for a display apparatus, this optical film 1 may be used by a single | mono layer, may laminate | stack several sheets of this optical film 1, and may make it a laminated body, or may combine with another film. By using in combination with another film, it can use for retardation film, a viewing angle compensation film, a viewing angle expansion film, an antireflection film, a polarizing film, a circularly polarizing film, an elliptically polarizing film, a brightness improving film, etc.

In particular, the present optical film 1 is used as a polymerizable liquid crystal compound of the present composition (1) by combining the compound (A) and the compound (3), thereby changing the optical properties in accordance with the alignment state of both, VA (vertical alignment) It can be adjusted as a retardation film for various liquid crystal display devices, such as a mode, an in-plane switching (IPS) mode, an optically compensated bend (OCB) mode, a twisted nematic (TN) mode, and a super twisted nematic (STN) mode.

2-1. Retardation film

Retardation film, which is a kind of optical film, is one of the preferred embodiments of the present optical film 1. A retardation film is used for converting linearly polarized light into circularly polarized light or elliptically polarized light, conversely converting circularly polarized light or elliptically polarized light into linearly polarized light, or converting the polarization direction of linearly polarized light.

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

n _{x> y} ≒ n _z positive A plate of n,

negative C plate of n _x ≒ n _y > n _z ,

a positive C plate of n _x ≒ n _y <n _z ,

positive O plate and negative O plate of n _x ? n _y ? n _z .

What is necessary is just to select the phase difference value of the retardation film 1 suitably from 30-300 nm according to the display apparatus used.

When using the retardation film 1 as a broadband (lambda) / 4 plate, Re (549) may be adjusted to 113-163 nm, Preferably it is 130-150 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 it tends to be able to polarize conversion with respect to light of a wide range of wavelengths. The wideband λ / 4 plate is a retardation film that expresses a 1/4 phase difference value with respect to light of each wavelength, and the wideband λ / 2 plate is a phase difference value that expresses 1/2 of the phase difference value with respect to light of each wavelength. It is a retardation film.

On the other hand, the film thickness can be prepared so that a desired phase difference can be provided by adjusting content of the polymeric liquid crystal compound contained in this composition (1) suitably. Since the retardation value (retardation value, Re ((lambda))) of the retardation film obtained is determined like Formula (4), in order to acquire desired Re ((lambda)), what is necessary is just to adjust (DELTA) n ((lambda)) and film thickness d suitably.

Re (λ) = d × Δn (λ) (4)

(Wherein Re (λ) represents the retardation value at wavelength λ nm, d represents the film thickness, and Δn (λ) represents the birefringence at wavelength λ nm)

2-2. Manufacturing method of this optical film 1

This optical film 1 can be manufactured by preparing a suitable base material, apply | coating this composition 1 on a base material, drying, and superposing | polymerizing the polymeric liquid crystal compound contained in this composition (1).

2-2-0. materials

As a base material which can be used for manufacture of this optical film, glass, a plastic sheet, a plastic film, and a translucent film are preferable, for example. As a translucent film, For example, Polyolefin film, such as polyethylene, a polypropylene, norbornene-type polymer; Polyvinyl alcohol film; Polyethylene terephthalate film; Polymethacrylic acid ester film; Polyacrylic acid ester film; Cellulose ester film; Polyethylene naphthalate film; Polycarbonate film; Polysulfone film; Polyether sulfone film; Polyether ketone film; Polyphenylene sulfide film, a polyphenylene oxide film, etc. are mentioned.

It is preferable that the base material used for manufacture of this optical film 1 consists of a material which has a hydroxyl group, and it is more preferable that it is a film which consists of a material which has a hydroxyl group. The film made of a material having a hydroxyl group may be a film obtained by forming a film having a hydroxyl group, or after forming a film (bulb film) by forming a material having a precursor group of a hydroxyl group, the precursor contained in the precursor film may be modified 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. Furthermore, after preparing the film which consists of a material which does not have a hydroxyl group or its precursor group, and apply | coated the coupling agent to the film surface, after attaching the monomer which has a hydroxyl group, or the polymer which has a hydroxyl group to the surface, it irradiates a radiation, a plasma, and an ultraviolet-ray. It may be obtained by a method of graft polymerization to be reacted. The film which arrange | positioned the material which has a hydroxyl group on a film surface is also made into the film which consists of a material which has a hydroxyl group in this specification. When using the film (base material) which consists of a material which has a hydroxyl group, there exists a tendency for the adhesiveness between a base material and this optical film to become higher.

Also in the film (base material) which consists of a material which has a hydroxyl group, the film obtained by saponifying a triacetyl cellulose film is preferable. By saponifying a triacetyl cellulose film, the triacetyl cellulose in a film saponifies and the film which consists of a material which has a hydroxyl group can be obtained easily, and it is especially preferable at the point of cost and handling at the time of manufacture.

Moreover, what is necessary is just to provide the orientation film in the surface which forms this optical film of the base material used for manufacture of this optical film 1. According to the orientation direction of an oriented film, after aligning the polymeric liquid crystal compound in this optical film to a desired direction, a polymeric liquid crystal compound can be polymerized. When using the base material which consists of a material which has a hydroxyl group, what is necessary is just to provide an oriented film on a base material.

2-2-1. Production of Unpolymerized Film

By apply | coating this composition (1) on a base material or an oriented film, an unpolymerized film can be obtained on a base material. When an unpolymerized film shows liquid crystal phases, such as a nematic phase, it has birefringence by monodomain orientation.

As a coating method on the base material of this composition (1), for example, extrusion coating method, direct gravure coating method, reverse gravure coating method, CAP (cap) coating method, die coating method, inkjet method, dip coating method, slit coating method, Spin coating, coating with a bar coater, and the like.

Among them, the composition can be continuously applied onto the substrate in a roll to roll format, and thus, by the CAP coating method, the inkjet method, the dip coating method, the slit coating method, the die coating method and the bar coater. Application is preferred.

This optical film 1 can also be handled in the state laminated | stacked with a base material. By laminating | stacking a base material to this optical film, when carrying a film, storing, etc., damage to this optical film is suppressed and can be handled easily.

When the present composition 1 is applied onto the alignment film after the alignment film is formed on the substrate in advance, the refractive index control by stretching is not necessary for the present optical film 1, so that the in-plane variation of birefringence becomes small. Therefore, the large this optical film which can cope with the enlargement of a flat panel display device FPD can be manufactured.

As a method of forming the alignment film, a method using an alignment polymer imparted with an orientation control force by rubbing (hereinafter referred to as a "rubbing method" in some cases), or a method using a photo-alignment polymer imparted with an orientation control force by irradiating polarized light ( Hereinafter, a monomolecular film having a long-chain alkyl group may be formed by using a "photo-alignment method"), a method of depositing silicon oxide on the surface of a substrate in all directions, and a Langmuir-Blodjet method (LB method). Forming method etc. are mentioned. Especially, the photo-alignment method is more preferable from a viewpoint of the orientation uniformity of the polymeric liquid crystal compound contained in this composition (1), the processing time of this optical film manufacture, and a processing cost. As an oriented film, even if it apply | coats this composition, it is preferable to have solvent resistance of the grade which does not melt | dissolve in the component contained in this composition (1), for example, the solvent contained in this composition (1). Moreover, the heat resistance with respect to the heat processing at the time of the removal of the solvent from an undried film, and the liquid crystal aligning of a polymeric liquid crystal compound is also calculated | required by an oriented film.

The optical alignment method is as described in the second aspect of the present invention.

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

2-2-2. Polymerization of Unpolymerized Films

The present optical film 1 can be obtained by polymerizing and curing the polymerizable liquid crystal compound contained in the unpolymerized film formed on the substrate or the alignment film. The orientation of the polymerizable liquid crystal compound is fixed and the optical film 1 is hardly affected by the birefringence change due to heat.

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

Although the unpolymerized film can be hardened as it is by irradiating light to the unpolymerized film formed by apply | coating this composition (1) on a base material or an orientation film, it is preferable to dry a unpolymerized film and to remove a solvent from an unpolymerized film. Do.

Although removal of a solvent may be performed in parallel with a polymerization reaction, it is preferable to remove a solvent before superposing | polymerizing. As the removal method, natural drying, ventilation drying, heat drying, reduced pressure drying, or the like, or a combination thereof may be mentioned. Especially, natural drying or heat drying is preferable, 0 degreeC-250 degreeC is preferable, as for the temperature at the time of natural drying or heat drying, 50 degreeC-220 degreeC is more preferable, 80 degreeC-170 degreeC is still more preferable. . The heating time is preferably 10 seconds to 60 minutes, and more preferably 30 seconds to 30 minutes. If heating temperature and a heat time exist in the said range, the thing in which heat resistance is not necessarily enough as a base material can be used.

By peeling a base material, the film (laminated film) in which the oriented film and this optical film were laminated | stacked can be obtained. In addition, the alignment film is peeled off to obtain the present optical film 1 in a single layer. Moreover, after bonding another base material (film or plate) to laminated | multilayer film, transfer can also be performed by peeling the base material and the orientation film laminated | stacked on this optical film 1.

3. Polarizer

This optical film 1 can be used for polarizing plate manufacture. The polarizing plate of this invention has at least one this retardation film 1. The polarizing plate using this retardation film 1 is demonstrated.

As a polarizing plate, as shown to FIG. 1 (a)-FIG. 1 (e), (1) the polarizing plate 4a by which this retardation film 1 and the polarizing film layer 2 were directly laminated (FIG. 1 (a)). ; (2) Polarizing plate 4b (FIG. 1 (b)) by which this retardation film 1 and polarizing film layer 2 were bonded through the adhesive bond layer 3 '; (3) The polarizing plate 4c which laminated | stacked this retardation film 1 and this retardation film 1 ', and laminated | stacked this retardation film 1' and the polarizing film layer 2 (FIG. 1 (c)) ); (4) The polarizing plate which bonded this retardation film 1 and this retardation film 1 'through the adhesive bond layer 3, and laminated | stacked the polarizing film layer 2 on this retardation film 1' ( 4d) (FIG. 1 (d)); And (5) the present retardation film 1 and the present retardation film 1 'are bonded through the adhesive layer 3, and the present retardation film 1' and the polarizing film layer 2 are bonded to the adhesive layer 3 '. The polarizing plates 4e (FIG. 1 (e)) etc. which were affixed on each other through the following are mentioned. An adhesive agent generically refers to an adhesive agent and / or an adhesive.

The polarizing film layer 2 may be a film having a polarizing function. For example, a film drawn by adsorbing an iodine or a dichroic dye to a polyvinyl alcohol film and a polyvinyl alcohol film are drawn to adsorb an oxo or dichroic dye. A film etc. are mentioned.

The polarizing film layer 2 may further be provided with the film used as a protective film as needed. Examples of the protective film include polyolefin films such as polyethylene, polypropylene and norbornene-based polymers, polyethylene terephthalate films, polymethacrylic acid ester films, polyacrylic acid ester films, cellulose ester films, polyethylene naphthalate films, polycarbonate films, and polysulfones. A film, a polyether sulfone film, a polyether ketone film, a polyphenylene sulfide film, a polyphenylene oxide film, etc. are mentioned.

It is preferable that the adhesive agent used for the adhesive bond layer 3 and the adhesive bond layer 3 'is an adhesive with high transparency and excellent heat resistance. As such an adhesive, an acrylic adhesive, an epoxy adhesive, a urethane adhesive, etc. are used, for example.

In addition, in a polarizing plate, as shown to FIG. 1 (c)-FIG. 1 (e), you may bond two or more this retardation films 1 containing this optical film 1 directly or via an adhesive bond layer.

4. Flat panel display

The flat panel display device of the present invention includes the present optical film 1 and is very useful as a member according to the flat panel display device. For example, the liquid crystal display device provided with the liquid crystal panel in which this optical film 1 and the liquid crystal panel were bonded, and the organic electroluminescent panel (henceforth "EL") in which this optical film 1 and the light emitting layer were bonded were used. The organic electroluminescence display provided is mentioned.

4-1. Liquid crystal display

As a liquid crystal display device of this invention, the liquid crystal display device etc. which are shown, for example in FIG.2 (a) and FIG.2 (b) are mentioned. The liquid crystal display device 10a illustrated in FIG. 2A is formed by bonding the polarizing plate 4 and the liquid crystal panel 6 of the present invention through the adhesive layer 5, and the liquid crystal display illustrated in FIG. 2B. The device 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 through the adhesive layer 5 and the adhesive layer 5'. According to the above configuration, by applying a voltage to the liquid crystal panel using an electrode (not shown), the orientation of the liquid crystal molecules is changed to enable monochrome display.

4-2. Organic EL display

As an organic electroluminescence display of this invention, the organic electroluminescence display shown in FIG. 3 is mentioned. As an organic electroluminescence display, the organic electroluminescence display 11 formed by bonding the polarizing plate 4 and organic electroluminescent panel 7 of this invention through the contact bonding layer 5 is 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), the compound included 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 circular polarizing plate. If it functions as a broadband circular polarizing plate, reflection of external light on the surface of the organic electroluminescence display 11 can be prevented.

According to this invention, the manufacturing method of an optical film using the composition and composition for optical film manufacture excellent in adhesiveness, and an optical film can be provided.

II. 2nd aspect of this invention

1. Second composition of the present invention (hereinafter, the second composition of the present invention is sometimes referred to as "this composition (2)", and the optical film produced from the present composition (2) is sometimes referred to as "this optical film ( 2)

The composition (2) is a compound having a carbon-carbon unsaturated bond and an active hydrogen reactive group in the (D) photo-aligned polymer (hereinafter sometimes referred to as "polymer (D)") and (B) molecule (hereinafter, "Compound (B)" accordingly).

1-1. Polymer (D)

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

As a method of forming the present optical film 2 (the present optical film 2 that is an alignment film) used to orient the liquid crystal compound, a method (rubbing method) and polarized light to impart an orientation regulating force to the polymer (D) by rubbing The method of giving an orientation regulation force to a polymer (D) by a irradiation (henceforth a "photo-alignment method") etc. are mentioned. Especially, the photo-alignment method which utilized the capability of the polymer (D) contained in this composition (2) from a viewpoint of the orientation uniformity, processing time, and processing cost of a liquid crystal compound is preferable. As this optical film 2 in this case, what has solvent resistance of the grade which does not melt | dissolve even if a liquid crystal compound is apply | coated is preferable. Moreover, when manufacturing this optical film 2, it is also required to have heat resistance with respect to the removal of the solvent from an undried film, and the heat processing at the time of orientation of a liquid crystal compound.

As the polymer (D), a polymer having a photosensitive structure is used. When polarized light is irradiated to the polymer (D) which has a photosensitive structure, the polymer (D) is orientated by isomerizing or bridge | crosslinking the irradiated part, and orientation control force is given to the present optical film 2 obtained. 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 full gid structure. The polymer (D) which has a photosensitive structure may be used independently for this composition (2), or may be used together 2 or more types. On the other hand, the polymer (D) can be obtained by a chain polymerization such as polycondensation, radical polymerization, anionic polymerization, cationic polymerization, etc. by dehydration, deamine, or the like using a monomer having a photosensitive structure, coordination polymerization, ring-opening polymerization, or the like. Moreover, these copolymers may be used using two or more types of monomers which have another photosensitive structure. As the polymer (D), Japanese Patent No. 4450261, Japanese Patent No. 4011652, Japanese Patent Application Laid-Open No. 2010-49230, Japanese Patent No. 4404090, Japanese Patent Publication No. 2007-156439, Japanese Patent Publication No. 2007-232934, etc. The photo-orientation polymer described is mentioned.

It is especially preferable if it forms a crosslinked structure by light irradiation as a polymer (D). If the polymer (D) forms a crosslinked structure, when forming the optically anisotropic layer, sufficient durability can be ensured when the composition for forming the optically anisotropic layer is applied.

0.1-30 mass% is preferable with respect to the gross mass of this composition (2), and, as for content of the polymer (D) in this composition (2), 0.2-15 mass% is more preferable.

The present optical film 2 can be manufactured by apply | coating this composition 2 on a base material. The base material mentioned in the 1st aspect of this invention is mentioned as a base material.

In order to manufacture this optical film 2 on a base material, when this composition 2 containing a solvent is used, manufacture of this optical film will become easy, and it is preferable. Water and an organic solvent are mentioned as a solvent contained in this composition (2). As an organic solvent, the organic solvent mentioned in the 1st aspect of this invention is mentioned. When using this composition (2) containing a solvent, a solvent may be used independently and may be used in combination of multiple types.

When this composition (2) contains a solvent, 100 mass parts-20000 mass parts are preferable with respect to 100 mass parts of solid content of this composition (2), More preferably, they are 200 mass parts-15000 mass parts. Solid content means the total amount of the component except low-volatile components, such as a solvent, in this composition (2).

1-2. The compound (B)

As a compound (B), the thing similar to the compound (B) contained in this composition (1) demonstrated in the 1st aspect of this invention is mentioned.

0.01-10 mass% is preferable with respect to the gross mass of this composition (2), and, as for content of the compound (B) in this composition (2), 0.02-5 mass% is more preferable. If it is in the said range, it will not reduce the reactivity of the polymer (D) in this composition (2).

2. This optical film (2)

It is preferable that this optical film 2 crosslinks the polymer (D) contained in this composition (2).

In order to form the coating film (undried film) for optical film manufacture from this composition (2), this composition (2) is apply | coated on a base material first. As a coating method on a base material, the method of apply | coating on the base material of this composition (1) demonstrated in the 1st aspect of this invention is mentioned.

Next, the coating film apply | coated on the base material is dried, and low boiling point components, such as a solvent contained in a coating film, are removed.

As a drying method, natural drying, ventilation drying, heat drying, reduced pressure drying, etc. or the method which combined these is mentioned, for example. It is preferable that it is 10-250 degreeC, and, as for a drying temperature, it is more preferable that it is 25-200 degreeC. Moreover, it is preferable that it is for 5 second-60 minutes, and, as for drying time, it is more preferable that it is for 10 seconds-30 minutes. If drying temperature and drying time are in the said range, when any of a base material is used, damage to a base material can be suppressed.

2-1. This optical film as an alignment film

In this optical film 2, what crosslinked the polymer (D) by polarized light irradiation functions as an orientation film. Specifically, when this composition 2 containing a solvent is apply | coated on a base material, and the obtained coating film is polarized light irradiation, and the polymer (D) is bridge | crosslinked, the obtained optical film 2 becomes an oriented film. It is preferable to dry and make a coating film (non-dried film) into a dry film before polarized light irradiation.

In order to provide orientation control force by the photo-alignment method, polarized light irradiation (for example, linearly-polarized ultraviolet-ray) is performed on the coating film formed from this composition (2). Polarized light irradiation can be performed using the apparatus of Unexamined-Japanese-Patent No. 2006-323060, for example. Further, on the coating film formed of the present composition (2), a photomask corresponding to a plurality of desired regions is prepared, and the patterned alignment film is formed by repeatedly performing polarized light irradiation (for example, linearly polarized ultraviolet light) through the photomask for each region. It may be formed. As a photomask, what formed the light shielding pattern on films, such as quartz glass, soda lime glass, or polyester, is used, for example. The portion exposed to the light shielding pattern is blocked from being exposed to light, and the portion not covered is transmitted to the exposed light. Since the influence of thermal expansion is small, quartz glass is preferable as a base material used for a photomask.

The example which manufactures a patterned alignment film is given. First, the 1st polarization which has a 1st polarization direction is irradiated to the coating film formed from this composition 2 through the 1st photomask which has a space part corresponding to a 1st pattern area | region (the rest area | region is a light shielding pattern). (First polarized light irradiation). By the 1st polarization irradiation, the direction of the orientation regulation force of a 1st pattern area is made to correspond to a 1st polarization direction. Subsequently, a second polarization direction different from the first polarization direction (eg, perpendicular to the first polarization direction) through a second photomask having a gap corresponding to the second pattern region (the remaining region is a light shielding pattern). 2nd polarized light which has a phosphorus direction) is irradiated (2nd polarized light irradiation). By 2nd polarization irradiation, the direction of the orientation regulation force of a 2nd pattern area | region corresponds to a 2nd polarization direction. Thereby, the alignment film which has some pattern area from which the direction of an orientation regulation force differs can be obtained. Further, by repeatedly performing polarized light irradiation through three or more types of photomasks, it is also possible to create a patterned alignment film having three or more pattern regions having different directions of orientation regulating force. In view of the reactivity of the polymer (D), the light irradiated with each polarized light irradiation is preferably an ultraviolet ray.

The film thickness of this optical film 2 is 10 nm-10000 nm, for example, Preferably it is 10 nm-1000 nm. When it is in the said range, when forming an optically anisotropic layer on this optical film 2, a liquid crystal compound can be orientated at a desired angle.

2-2. Retardation film (2)

What formed the optical anisotropic layer on this optical film 2 and expressed retardation is a retardation film (henceforth called "this retardation film 2"). The composition for optically anisotropic layer formation is called "the composition for optically anisotropic layer formation" as follows.

2-2-1. Liquid crystal compound

An optically anisotropic layer can be formed, for example by orienting a liquid crystal compound, and the composition for optically anisotropic layer formation contains such a liquid crystal compound, Preferably a polymeric liquid crystal compound. As a composition for optically anisotropic layer forming, what may contain 1 type of liquid crystal compounds may be sufficient as what contains other 2 or more types of liquid crystal compounds.

As a liquid crystal compound, the polymeric liquid crystal compound demonstrated in the 1st aspect of this invention is mentioned, for example, The compound containing group represented by Formula (X1) is preferable.

2-2-2. additive

The composition for optically anisotropic layer formation may contain additives, such as a photoinitiator, a polymerization inhibitor, a photosensitizer, a photoinitiator, a solvent, and a chiral agent, in addition to a liquid crystal compound. It is preferable to contain a solvent especially an organic solvent from the point that film-forming of the composition for optically anisotropic layer formation itself becomes easy at the time of an optically anisotropic layer formation. Moreover, when a liquid crystal compound is a polymeric liquid crystal compound, it is preferable if the composition for optically anisotropic layer formation contains the polymerization initiator which has a function which hardens the film which formed the composition for optically anisotropic layer formation into a film.

As each additive, the additive illustrated by the 1st aspect of this invention is mentioned.

The unpolymerized film can be obtained on this optical film 2 by apply | coating the composition for optically anisotropic layer formation on this optical film 2. When an unpolymerized film shows liquid crystal phases, such as a nematic phase, it has birefringence by monodomain orientation.

As a method of apply | coating the composition for optically anisotropic layer forming on this optical film 2, the method illustrated as a method of apply | coating this composition 2 on a base material can be applied. In particular, the composition for forming an optically anisotropic layer can be applied onto the optical film continuously seen in a roll-to-roll format, by the CAP coating method, the inkjet method, the dip coating method, the slit coating method, the die coating method and the bar coater. Application is preferred. For example, in the case of a roll-to-roll type, it is continuous to apply | coat this composition 2 on a base material, to form this optical film 2 on a base material, and to form an optically anisotropic layer on the obtained this optical film 2 further. It may also be carried out.

You may use this optical film 2 in the state laminated | stacked with the base material. By stacking the base material on the optical film 2, the damage of the optical film 2 is suppressed when the film is transported or stored, and can be easily handled.

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

As a method of polymerizing and hardening a liquid crystal compound, the method illustrated by the 1st aspect of this invention is mentioned.

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

The characteristic of this retardation film 2 is the same as the characteristic of this retardation film 1 demonstrated in the 1st aspect of this invention.

4. Polarizer

This optical film 2 can be used for polarizing plate manufacture.

As a polarizing plate, the thing similar to the polarizing plate demonstrated by the 1st aspect of this invention is mentioned.

5. Flat Panel Display

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

As a flat panel display apparatus, the same thing as the flat panel display apparatus demonstrated in 1st aspect of this invention is mentioned.

According to this invention, the manufacturing method of an optical film using the composition and composition for optical film manufacture excellent in adhesiveness, and an optical film can be provided.

III. 3rd aspect of this invention

The 3rd aspect of this invention is the optical film formed by laminating | stacking a base material, the A layer formed from the composition (A), and the B layer formed from the composition (B) in this order (henceforth "this optical film 3"). Is called).

1. Equipment

As a base material, the same thing as the description demonstrated by 1st aspect of this invention is mentioned, for example.

As for a base material, it is more preferable that it is a film (base material) which consists of a material which has a hydroxyl group demonstrated in the 1st aspect of this invention. When using the film (base material) which consists of a material which has a hydroxyl group, in addition to the adhesiveness between A-layer / B-layer, there exists a tendency for adhesiveness between base materials / A-layer to become higher, and this high quality optical film can be obtained.

In the film which consists of a material which has a hydroxyl group, when the film which consists of materials obtained by saponifying a triacetyl cellulose is used, since adhesiveness between base materials / A layer becomes more favorable by the synergistic effect with a composition (A), it is preferable. Moreover, the film which consists of a material obtained by saponifying a triacetyl cellulose is also preferable at the point which can obtain the film (triacetyl cellulose film) itself which consists of triacetyl cellulose which is the precursor film easily in a market.

2. Composition (A)

The composition (A) is the composition (2) described in the second aspect of the present invention. (D) Photo-alignment polymer in composition (A) is corresponded to polymer (D) in composition (2), and (B-1) carbon-carbon unsaturated bond and active hydrogen reactivity in composition (A) The compound which has a group is corresponded 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 has a (B-1) carbon-carbon unsaturated bond and an active hydrogen reactive group in the composition (B). The compound corresponds to the compound (B) in the composition (1), and the (C) photopolymerization initiator in the composition (B) corresponds to the (C) photopolymerization initiator 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 Corporation) may be mentioned. In addition, although the compound (B-1) contained in a composition (A) and the compound (B-2) contained in a composition (B) may mutually be same or different, it is preferable if both are the same. If a compound (B-1) and a compound (B-2) are commercially available products, such as Laromer LR-9000, it is preferable at the point that a composition (A) and a composition (B) can be prepared easily.

4. Pattern optical film

This optical film 3 is a film which can transmit light, and is a film which has an optical function. Optical function means refraction, birefringence, etc.

It is preferable that this optical film 3 is excellent in transparency in a visible light region, and can be used as a member for various display devices, especially a member for flat panel display devices. The thickness of this optical film 3 can be suitably adjusted according to the use of this optical film, It is preferable that it is 0.1-10 micrometers, It is more preferable that it is 0.2-5 micrometers in the point which makes photoelasticity small.

10-200 micrometers is preferable and, as for the thickness of a base material, 15-100 micrometers is more preferable. In addition, the thickness (film thickness) of the A layer is preferably 0.01 to 10 µm (10 to 10000 nm), and more preferably 0.01 to 1 µm (10 to 1000 nm). The thickness (film thickness) of B layer is 0.1-10 micrometers, for example, and 0.2-5 micrometers is preferable.

When using this optical film 3 for a display apparatus, this optical film may be used by a single | mono layer, several optical films may be laminated | stacked, and may be laminated | stacked, and may be combined with another film. By using in combination with another film, it can use for retardation film, a viewing angle compensation film, a viewing angle expansion film, an antireflection film, a polarizing film, a circularly polarizing film, an elliptically polarizing film, a brightness improving film, etc. In addition, this optical film may be what laminated | stacked several types of base materials in the specific example of the base material already illustrated, may have a multiple layer A layer, and may have a multiple layer B layer. On the other hand, when it has a several layer A layer, for example, after forming a 1st A layer using a composition (A) on a base material, before forming a B layer, it is a composition (A) on a 1st A layer. Means forming a second A layer using another composition (A).

In particular, the present optical film changes the optical characteristics according to the alignment state of the polymerizable liquid crystal compound at the time of forming the B layer. It can adjust as retardation film for various liquid crystal display devices, such as a (twisted nematic) mode and a super twisted nematic (STN) mode.

4-1. Retardation film

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

As retardation film, the retardation film mentioned by the 1st aspect of this invention is mentioned.

4-2. Manufacturing method of this optical film

The manufacturing method of this optical film includes the process of the following <1>-<4>, for example. In addition, this manufacturing method is a method of using what contains a solvent together with a composition (A) and a composition (B), and is a manufacturing method of this optical film which has 1 type of base material, A layer, and B layer, respectively.

Forming a first coating film on the substrate by applying the <1> composition (A) onto the substrate (first coating film forming step);

<2> A step of converting the first coating film to the A layer by crosslinking (B-1) contained in the first coating film by <1> (A layer forming step);

<3> process of forming a 2nd coating film on A layer by apply | coating composition (B) on A layer formed by <2> (2nd coating film formation process);

<4> Process of polymerizing the polymerizable liquid crystal compound contained in the 2nd coating film formed by <3> (B layer formation process)

A 1st coating film formation process is a process of forming a 1st coating film on a base material by preparing a base material and apply | coating a composition (A) on a base material.

As a coating method of a composition (A), the method illustrated by the 2nd aspect of this invention is mentioned.

In the A layer forming step, the alignment control force is imparted by photoaligning (crosslinking) the photoalignable polymer included in the first coating film formed on the substrate, preferably the dried first coating film, by the first coating film forming step. Thus, the first coating film is switched to the A layer. The layer A functions as an alignment film (alignment layer) because the alignment regulating force is imparted.

As a drying method, the method illustrated by the 2nd aspect of this invention is mentioned.

As a method of providing orientation control force by photo-alignment, the method illustrated by the 2nd aspect of this invention is mentioned.

The second coating film forming step is a step of forming a second coating film (unpolymerized film) by applying the composition (B) on the A layer formed in the A layer forming step. When the polymeric liquid crystal compound contained in a 2nd coating film shows liquid crystal phases, such as a nematic phase, it has birefringence by monodomain orientation.

As a method of apply | coating a composition (B) on A layer in a 2nd coating film formation process, the method quoted in the 1st aspect of this invention is mentioned.

In the B layer forming step, the present optical film 3 can be obtained by polymerizing and curing the polymerizable liquid crystal compound contained in the second coating film formed on the A layer. The layer B is fixed in the orientation of the polymerizable liquid crystal compound and is less likely to be affected by the birefringence change due to heat. In addition, the adhesion between the A layer and the B layer is due to 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. It is very good.

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

Although it is also possible to irradiate light as it is to the 2nd coating film formed by apply | coating composition (B) on A-layer, B layer can be formed, but a low volatile component, such as a solvent, can be made from the 2nd coating film by drying It is preferable to remove.

In addition, although the low volatile component may be removed in parallel with a polymerization reaction, it is preferable to remove most solvents before superposing | polymerizing. As the removal method, the method illustrated as a drying method of a 1st coating film is employ | adopted. Especially, natural drying or heat drying is preferable, 0 degreeC-250 degreeC is preferable, as for the temperature at the time of natural drying or heat drying, 50 degreeC-220 degreeC is more preferable, 80 degreeC-170 degreeC is still more preferable. . The heating time is preferably 10 seconds to 60 minutes, and more preferably 30 seconds to 30 minutes. As long as heating temperature and a heat time are in the said range, the base material and / or A layer can use what heat resistance is not necessarily sufficient.

5. Use as a polarizing plate of this optical film

This optical film can be used for polarizing plate manufacture as retardation film.

As a polarizing plate, the thing similar to the polarizing plate demonstrated by the 1st aspect of this invention is mentioned.

6. Flat Panel Display

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

As a flat panel display apparatus, the same thing as the flat panel display apparatus demonstrated by the 1st aspect of this invention is mentioned.

According to this invention, the optical film excellent in the adhesiveness between an orientation layer and an optically anisotropic layer can be provided.

Example

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

<1st aspect of this invention>

1. Synthesis Example of Polymerizable Liquid Crystal Compound

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

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 heating the obtained dispersion liquid at 80 degreeC, 190.5 g of bromoacetic acid tert-butyl were dripped over 30 minutes. The liquid mixture after dripping was reacted at 130 degreeC for 2 hours. After cooling the reaction solution to room temperature, 600 mL of methyl isobutyl ketone was added, and water washing was performed using 1200 mL of pure water. The organic layer was further washed with 1000 mL of pure water twice to recover the organic layer. After dehydration with anhydrous sodium sulfate, the solvent was distilled off by an evaporator. The residue was dissolved in 240 g of acetic acid, 72 g of hydrobromic acid aqueous solution was added, and the mixture was stirred at 40 ° C for 1 hour. After cooling to room temperature, 150 g of 1 N (1 mol / L) -hydrochloric acid was added, and the precipitated white powder was collected by filtration. The obtained white powder was further washed with 1N hydrochloric acid, and then dried in vacuo to give 4,6-dimethylbenzofuran-2-carboxylic acid as 81.7 g yellow powder. Yield was 44% based on 4,6-dimethylsalicylaldehyde.

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. The resulting suspension was cooled in an ice bath, and then a mixed solution of 88.7 g of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride and 300 g of chloroform was added over 4 hours and allowed to react at room temperature for 48 hours. The obtained liquid mixture was concentrated and crystallized by adding 1 N-hydrochloric acid and a mixed solution of water-methanol (2 vol parts of water and 1 vol part of methanol). The obtained precipitate was collected by filtration, and a mixed solution of water-methanol (2 vol parts of water and 1 vol part of methanol) was added. The precipitated pale yellow precipitate was collected by filtration, washed with a mixed solution of water-methanol (2 vol parts of water and 1 vol part of methanol), and dried in vacuo to give 124.2 g of 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 compound (11-a), 9.2 g of 2,4-bis (4-methoxyphenyl) -1,3-dithia-2,4-diphosphetane-2,4-disulfide (Lawson's reagent) and 1200 g of toluene were mixed. After heating up the obtained liquid mixture to 110 degreeC, it was made to react at the same temperature for 8 hours. After cooling to room temperature, the mixture was washed with 1N-sodium hydroxide aqueous 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 in vacuo to give 109.2 g of compound (11-b) as a light yellow powder. The yield was 85% based on compound (11-a).

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

60 g of compound (11-b), 53.8 g of potassium hydroxide, and 1000 g of water were mixed. The obtained liquid mixture was stirred under ice cooling. Then, 133 g of potassium ferricyanide and 51 g of methanol were added to react. Furthermore, it reacted at room temperature for 36 hours, and the yellow precipitate which precipitated was filtered out. The precipitate taken by filtration was washed with a mixed solvent of n-heptane-toluene (3 parts by volume of n-heptane, 1 part by volume of toluene), and the resulting yellow powder was dried in vacuo to give 51.3 g of Compound (11-c) as a yellow solid. Got it. The yield was 86% based on compound (11-b).

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

40 g of compound (11-c) and 400 g (10-fold mass) of pyridinium chloride were mixed, the resulting mixture was heated to 180 ° C, and reacted at the same temperature for 3 hours. The obtained liquid mixture was added to ice, and the precipitate deposited was collected by filtration. After washing with water with water, washing with toluene and vacuum drying gave 36.6 g of a yellow solid containing Compound (11-d) as a main component. The yield was 99% based on 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 compound (11-d), 98.8 g of 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 liquid mixture under ice cooling. The obtained reaction solution was reacted overnight at room temperature, filtered using a filter medium in which silica gel was precoated, and then concentrated under reduced pressure. Methanol was added to the residue to crystallize. The crystals were collected by filtration, redissolved in chloroform, 2.3 g of activated carbon was added, and the mixture was stirred at room temperature for one hour. The solution was filtered and the filtrate was concentrated under reduced pressure until the volume was 1/3 by evaporator, methanol was added while stirring, and the precipitated white precipitate was collected by filtration, washed with heptane and dried in vacuo to compound (A11-1). 74.5 g was obtained 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 synthesize | combined by the method of Unexamined-Japanese-Patent No. 2010-31223.

1-9. Synthesis of Photo-Oriented Polymer (Z)

Photo-oriented polymer (Z) was used as Macromol. Chem. Phys. 197, 1919-1935 (1996).

1.5 parts of monomers (monomer (Z-a)) represented by the formula (Z-a) and 0.1 part of methyl methacrylate were dissolved in 16 parts of tetrahydrofuran and allowed to react at 60 ° C for 24 hours. Subsequently, after cooling the reaction liquid to room temperature, the photo-alignment polymer (Z) was obtained by dripping into the liquid mixture of toluene and methanol. The number average molecular weight of the photo-alignment polymer (Z) was 33000. In the photo-alignment polymer (Z), the content rate of the structure derived from the monomer (Z-a) was 75 mol%.

The polystyrene conversion number average molecular weight (Mn) of the obtained photo-alignment polymer (Z) was measured on condition of the following using GPC method.

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

After mixing each component shown in the table and stirring the obtained solution at 80 degreeC for 1 hour, it cooled to room temperature and prepared the composition.

Irg369 (Irgacure 369 (made by BASF Japan)) and the leveling agent used BYK361N (made by Vikchem Japan) as a photoinitiator. A polymeric liquid crystal compound (LC242) is a BASF Corporation make, and is a compound of the following formula.

3. Production Example of Optical Film

The 5% toluene solution of the photo-alignment polymer (Z) was apply | coated on the saponification-treated triacetyl cellulose film, and after drying, the film of 300 nm in thickness was formed. Subsequently, linearly polarized light was irradiated for 5 minutes at an illuminance of 15 mW / cm 2 using a spotcure (SP-7, manufactured by Ushio Denki Co., Ltd.) with a polarized UV irradiation jig in the direction perpendicular to the surface (polarized UV irradiation). did. The composition of the table | surface was apply | coated using the bar coater to the surface which polarized UV irradiation was performed, it heated at 130 degreeC, and the film orientated to the liquid crystal phase was obtained. Then, the optical film was produced by irradiating the ultraviolet-ray for 1 minute with the illuminance of 40 mW / cm <2> in wavelength 365nm using the unicure (VB-15201BY-A, Ushio Denki Corporation make) in the state cooled to room temperature. .

[Evaluation of adhesion]

According to JIS-K5600, peeling resistance was evaluated using the Cotech Co., Ltd. crosscut guide I series (CCI-1, 1 mm interval, for 25 masses), and the residual number of the liquid crystal layer was counted. The results are shown in the table. It was confirmed that this optical film is excellent in adhesiveness.

[Measurement of Optical Properties]

The phase difference value of the optical film was measured by the measuring device (KOBRA-WR, the product made by Oji Geisokukiki Co., Ltd.). The retardation value was measured at a wavelength (λ) of 549 nm. The results are shown in the table.

<2nd aspect of this invention>

1. Synthetic Example

"1-9. In 1st aspect of this invention. Synthesis of Photo-Oriented Polymer (Z) ”The photo-oriented polymer (Z) was synthesized in the same manner.

2. Preparation of Composition

After mixing each component shown in the table and stirring the obtained solution at 80 degreeC for 1 hour, it cooled to room temperature and prepared the composition.

The compound (B) used Laromer (trademark) LR-9000 (made by BASF Japan).

Irg369 (Irgacure 369 (made by BASF Japan)) and the leveling agent used BYK361N (made by Vikchem Japan) as a photoinitiator. LC242 is manufactured by BASF Corporation, and is a compound of the following formula.

3. Production Example of Optical Film

The compositions shown in Examples 3, 4 and Comparative Example 2 were applied onto the saponified triacetyl cellulose film, and after drying, a film having a thickness of 280 nm was formed. Subsequently, linearly polarized light was irradiated for 5 minutes at the illuminance of 15 mW / cm <2> using the spotcure (SP-7, Ushio Denki Co., Ltd.) with a polarization UV irradiation jig in a perpendicular direction to the surface. The composition for optically anisotropic layer formation of the table | surface was apply | coated using the bar coater to the surface which performed polarized UV, and it heated at 120 degreeC, and obtained the film orientated in the liquid crystal phase. Then, the optical film was produced by irradiating the ultraviolet-ray for 1 minute with the illuminance of 40 mW / cm <2> in wavelength 365nm using the unicure (VB-15201BY-A, Ushio Denki Corporation make) in the state cooled to room temperature. .

[Evaluation of adhesion]

According to JIS-K5600, peeling resistance was evaluated using the Cotech Co., Ltd. crosscut guide I series (CCI-1, 1 mm interval, for 25 masses), and the residual number of the liquid crystal layer was counted. The results are shown in the table. It was confirmed that this optical film is excellent in adhesiveness.

[Measurement of Optical Properties]

The phase difference value of the optical film was measured by the measuring device (KOBRA-WR, the product made by Oji Geisokukiki Co., Ltd.). The retardation value was measured at a wavelength (λ) of 549 nm. The results are shown in the table.

<3rd aspect of this invention>

1. Synthetic Example

"1-9. In 1st aspect of this invention. Synthesis of Photo-Oriented Polymer (Z) ”The photo-oriented polymer (Z) was synthesized in the same manner.

2. Preparation of Composition

After mixing each component shown in the table and stirring the obtained solution at 80 degreeC for 1 hour, it cooled to room temperature and prepared the composition.

The compound (B-1) used Laromer (trademark) LR-9000 (made by BASF Japan).

Irg369 (Irgacure 369 (made by BASF Japan)) and the leveling agent used BYK361N (made by Vikchem Japan) as a photoinitiator. LC242 is manufactured by BASF Corporation, and is a compound of the following formula.

3. Production Example of Optical Film

The composition (A-1) was apply | coated on the saponified triacetyl cellulose film, and after drying, the film | membrane of thickness 280 nm was formed. Subsequently, linearly polarized light was irradiated for 5 minutes at the illuminance of 15 mW / cm <2> using the spotcure (SP-7, Ushio Denki Co., Ltd.) with a polarization UV irradiation jig in a perpendicular direction to the surface. The composition (B-1) was apply | coated to the surface which polarized UV was performed using the bar coater, it heated at 120 degreeC, and the film orientated to the liquid crystal phase was obtained. Then, the optical film was produced by irradiating the ultraviolet-ray for 1 minute with the illuminance of 40 mW / cm <2> in wavelength 365nm using the unicure (VB-15201BY-A, Ushio Denki Corporation make) in the state cooled to room temperature. .

[Evaluation of adhesion]

According to JIS-K5600, peeling resistance was evaluated using the Cotech Co., Ltd. crosscut guide I series (CCI-1, 1 mm interval, for 25 masses), and the residual number of the liquid crystal layer was counted. The results are shown in the table. It was confirmed that this optical film is excellent in adhesiveness.

[Measurement of Optical Properties]

The phase difference value of the optical film was measured by the measuring device (KOBRA-WR, the product made by Oji Geisokukiki Co., Ltd.). The retardation value was measured at a wavelength (λ) of 549 nm. The results are shown in the table.

This invention is very useful for manufacture of the optical film used for a liquid crystal display device, an organic electroluminescence display, etc., and its industrial value is high.

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

Claims (39)

A composition comprising the following (A), (B) and (C):
(A) polymerizable liquid crystal compound
(B) a compound having a carbon-carbon unsaturated bond and an active hydrogen reactive group in the molecule
(C) Photoinitiator. 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 formula (X), n represents the integer of 1-10, R <^1> represents a C2-C20 divalent aliphatic or alicyclic hydrocarbon group, or a C5-C20 divalent aromatic hydrocarbon group. Two R ^{2 '} in each repeating unit is a group represented by -NH- on one side and-[NC (= O) -R ^3' ]-on the other side. R ^{3 '} represents a group having a hydroxyl group or a carbon-carbon unsaturated bond.
R ^{3 'wherein} at least one R ^3' is a carbon group having a carbon unsaturated bond. The composition according to any one of claims 1 to 3, wherein (A) is a compound represented by formula (A).

[In 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 the C6-C12 monovalent aromatic heterocyclic group which may have a substituent, or may have a C6-C12 monovalent aromatic hydrocarbon group.
Q ³ and Q ⁴ each independently represent a hydrogen atom or a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, or a monovalent having 6 to 20 carbon atoms which may have a substituent. Aromatic hydrocarbon group, halogen atom, cyano group, nitro group, -NR ² R ³ or -SR ² , or Q ³ and Q ⁴ are bonded to each other, and aromatic ring or aromatic heterocyclic ring together with the carbon atom to which they are respectively bonded To form. 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 described above. The methine group which comprises a group may be substituted by the 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 of claim 4, wherein (A)
A composition in which L ^{1 in} formula (A) is a group represented by formula (A1), and L ² is a compound represented by formula (A2).
P ¹ -F ^1- (B ¹ -A ¹ ) _k -E ^1- (A1)
P ² -F ^2- (B ² -A ² ) _l -E ^2- (A2)
[In Formula (A1) and Formula (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 Indicates binding.
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, a sulfur atom, or -NH. It may be substituted by-and the methine group which comprises the said alicyclic hydrocarbon group may be substituted by the tertiary nitrogen atom.
k and 1 respectively independently represent the integer of 0-3. When k is an integer of 2 or more, the plurality of B ¹ may be the same as or different from each other, and the plurality of A ¹ may be the same or different from each other. When l is an integer of 2 or more, the plurality of B ² may be the same as or different from each other, and the plurality of A ² may be the same or different from each other.
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 described above.] The optical film formed by superposing | polymerizing in the polymeric liquid crystal compound contained in the composition in any one of Claims 1-5. The manufacturing method of the optical film containing the following (1) and (2):
(1) Process of apply | coating the composition of any one of Claims 1-5 on a base material;
(2) Process of forming an optical film by superposing | polymerizing the polymerizable liquid crystal compound contained in the coating film apply | coated on the base material by (1). The manufacturing method of the optical film of Claim 7 in which a base material consists of a material which has a hydroxyl group. The method for producing an optical film according to claim 8, wherein the material having a hydroxyl group is a material obtained by saponifying triacetyl cellulose. The manufacturing method of the optical film as described in any one of Claims 7-9 with which the oriented film in which the base material was formed with the photo-alignment polymer on the surface was provided. The method for producing an optical film according to claim 10, wherein the alignment film is formed by forming a crosslinked structure of a photoalignable polymer by light irradiation. The optical film obtained by the manufacturing method in any one of Claims 7-11. The optical film of Claim 6 or 12 which has retardation. The polarizing plate containing the optical film as described in any one of Claims 6, 12, or 13. The flat panel display device provided with the optical film as described in any one of Claims 6, 12, or 13. A composition comprising the following (D) and (B):
(D) photo-oriented polymer
(B) A compound having a carbon-carbon unsaturated bond and an active hydrogen reactive group in the molecule. The composition according to claim 16, wherein (D) is a photo-oriented 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 formula (X), n represents the integer of 1-10, R <^1> represents a C2-C20 divalent aliphatic or alicyclic hydrocarbon group, or a C5-C20 divalent aromatic hydrocarbon group. Two R ^{2 '} in each repeating unit is a group represented by -NH- on one side and-[NC (= O) -R ^3' ]-on the other side. R ^{3 '} represents a group having a hydroxyl group or a carbon-carbon unsaturated bond.
R ^{3 'wherein} at least one R ^3' is a carbon group having a carbon unsaturated bond. The optical film formed by bridge | crosslinking the photo-alignment polymer contained in the composition as described in any one of Claims 16-19. The manufacturing method of the optical film containing the following (1) and (2):
(1) Process of apply | coating the composition of any one of Claims 16-19 on a base material;
(2) A process of forming an optical film by crosslinking the photo-alignment polymer contained in the coating film apply | coated on the base material by (1). The manufacturing method of the optical film of Claim 21 in which a base material consists of a material which has 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. The optical film obtained by the manufacturing method in any one of Claims 21-23. A phase difference plate formed by further forming an optically anisotropic layer on the optical film of Claim 20 or 24. The polarizing plate containing the optical film of Claim 20 or 24. The flat panel display device provided with the optical film of Claim 20 or 24. As an optical film formed by laminating the base material, the A layer formed of the composition (A) and the B layer formed of the composition (B) in this order,
The optical film containing the following (D) and (B-1), and a composition (B) containing the following (A), (B-2) and (C):
(D) photo-oriented polymer
(B-1) A compound having a carbon-carbon unsaturated bond and an active hydrogen reactive group
(A) polymerizable liquid crystal compound
(B-2) A compound having a carbon-carbon unsaturated bond and an active hydrogen reactive group
(C) Photoinitiator. The optical film according to claim 28, wherein (D) is a photo-alignment 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) together 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 formula (X), n represents the integer of 1-10, R <^1> represents a C2-C20 divalent aliphatic or alicyclic hydrocarbon group, or a C5-C20 divalent aromatic hydrocarbon group. Two R ^{2 '} in each repeating unit is a group represented by -NH- on one side and-[NC (= O) -R ^3' ]-on the other side. R ^{3 '} represents a group having a hydroxyl group or a carbon-carbon unsaturated bond.
R ^{3 'wherein} at least one R ^3' is a carbon group having a carbon unsaturated bond. 32. The optical film according to any one of claims 28 to 31, wherein the layer A is formed by crosslinking of (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. The optical film of any one of Claims 28-34 which has retardation. The manufacturing method of the optical film containing the process of the following <1>-<4>:
Process of forming a 1st coating film on a base material by apply | coating the composition (A) containing <1> or less (D) and (B-1) on a base material;
(D) photo-oriented 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 to the A layer by crosslinking (D) contained in the first coating film coated on the substrate by <1>;
Forming a second coating film on the A layer by applying the composition (B) containing the following (A), (B-2) and (C) on the A layer formed by <3><2>;
(A) polymerizable liquid crystal compound
(B-2) A compound having a carbon-carbon unsaturated bond and an active hydrogen reactive group
(C) photopolymerization initiator
<4> A step of polymerizing the polymerizable liquid crystal compound contained in the second coating film formed by <3>. The optical film obtained by the manufacturing method of Claim 36. The polarizing plate containing the optical film as described in any one of Claims 28-35 and 37. The flat panel display provided with the optical film as described in any one of Claims 28-35 and 37.

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