KR20140043422A - Colorant, coloring composition, color filter and display device - Google Patents

Abstract

The objective of the present invention is to provide a coloring composition capable of forming a coloring layer with both high heat resistance and improved voltage holding ratios and a colorant suitable for the coloring composition. The solving means of the present invention is the coloring composition containing components (A), (B) and (C), wherein (A) is a xanthene colorant which has a polymerizable unsaturated group in a chromophoric part, (B) is a binder resin, and (C) is a crosslinking agent.

Description

COLORING COMPOSITION, COLOR FILTER AND DISPLAY DEVICE,

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a coloring composition, a color filter, and a display device, and more particularly to a coloring composition, a color filter and a display device which are suitably used for a color filter such as a transmissive or reflective color liquid crystal display device, , A coloring composition containing the coloring agent, a color filter including the coloring layer containing the coloring agent, and a display element comprising the color filter.

When a color filter is manufactured using a coloring and radiation-sensitive composition, a pigment-dispersed coloring and radiation-sensitive composition is applied onto a substrate and dried, and then the dry film is irradiated with a desired pattern (hereinafter referred to as "exposure" ), And then developing them to obtain pixels of respective colors (Patent Documents 1 and 2). Further, a method of forming a black matrix using a photopolymerizable composition in which carbon black is dispersed (Patent Document 3) is also known. There is also known a method of obtaining pixels of respective colors by an ink-jet method using a pigment-dispersed type colored resin composition (Patent Document 4).

However, it is known that it is effective to use a dye as a coloring agent in order to realize high brightness and high color purity of a display element or high definition of a solid-state image pickup element. For example, Patent Document 5 proposes the use of a xanthene dye having a specific structure.

Japanese Patent Application Laid-Open No. 2-144502 Japanese Patent Laid-Open Publication No. 3-53201 Japanese Patent Application Laid-Open No. 6-35188 Japanese Patent Application Laid-Open No. 2000-310706 Japanese Patent Application Laid-Open No. 2008-242311

However, the xanthan dyes proposed in Patent Document 5 have a problem that the voltage retention rate of the color filter is deteriorated. From the above background, development of a colored composition suitable for the production of a color filter having a satisfactory voltage holding ratio is strongly desired.

Accordingly, it is an object of the present invention to provide a coloring composition suitable for forming a colored layer excellent in voltage holding ratio. It is still another object of the present invention to provide a color filter comprising a colored layer formed from the colored composition and a display device including the color filter.

In view of such facts, the present inventors have conducted intensive studies and found that the above problems can be solved by using a colorant having a specific structure, and the present invention has been accomplished.

That is, the present invention provides a coloring composition containing the following components (A), (B) and (C).

(A) a xanthene colorant having a polymerizable unsaturated group in the coloring portion (hereinafter also referred to as " present colorant ");

(B) a binder resin; And

(C) a crosslinking agent.

The present invention also provides a color filter comprising a coloring layer formed using the coloring composition and a display element comprising the color filter. Here, the " colored layer " means each color pixel, a black matrix, a black spacer, etc. used in the color filter.

The present invention also provides a colorant having a structure represented by the following formula (1).

In formula (1),

R ^a represents a group having ^a polymerizable unsaturated group,

R ¹ to R ⁴ independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, or a phenyl group (said alkyl group, cycloalkyl group or phenyl group may have a substituent)

R ⁵ and R ⁶ independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a chlorine atom,

r represents an integer of 1 to 5, and when r is an integer of 2 or more, a plurality of R ^a may be the same or different;

When the coloring composition of the present invention is used, a colored layer excellent in the voltage holding ratio can be formed. Therefore, the coloring composition of the present invention can be suitably used for the production of various color filters including a color filter for a display element, a color filter for color separation of a solid-state image pickup element, a color filter for an organic EL display element, and a color filter for an electronic paper .

Hereinafter, the present invention will be described in detail.

Coloring composition

Hereinafter, the structural component of the coloring composition of this invention is demonstrated in detail.

- (A) Colorant -

The coloring composition of the present invention contains (A) this coloring agent as a coloring agent.

This colorant is not particularly limited as long as it is a xanthan-based colorant having a polymerizable unsaturated group in a color-developing part. The polymerizable unsaturated group is preferably a (meth) acryloyl group, a vinylaryl group, a vinyloxy group, an allyl group, or the like. Among them, a (meth) acryloyl group is preferable.

In the present invention, the present inventors contemplate that the present colorant exhibits a satisfactory voltage holding ratio because the polymerizable unsaturated group has a polymerizable unsaturated group, whereby a polymerizable unsaturated group undergoes a crosslinking reaction during exposure or post-baking to inhibit the elution of the dye into the liquid crystal.

Preferred examples of the present coloring agent in the present invention include a xanthene colorant having a structure represented by the following formula (1).

In formula (1),

R ^a represents a group having ^a polymerizable unsaturated group,

R ¹ to R ⁴ independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, or a phenyl group (said alkyl group, cycloalkyl group or phenyl group may have a substituent)

R ⁵ and R ⁶ independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a chlorine atom,

r represents an integer of 1 to 5, and when r is an integer of 2 or more, a plurality of R ^a may be the same or different;

Examples of the alkyl group having 1 to 8 carbon atoms for R ¹ to R ⁴ include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert- Tert-butyl, tert-amyl, hexyl, heptyl, octyl, isooctyl, tert-octyl and 2-ethylhexyl. Among them, an alkyl group having 1 to 6 carbon atoms is preferable, and an alkyl group having 1 to 4 carbon atoms is preferable.

Examples of the cycloalkyl group having 3 to 8 carbon atoms for R ¹ to R ⁴ include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group. Among them, a cycloalkyl group having 5 to 7 carbon atoms is preferable, and a cyclohexyl group is more preferable.

The alkyl group having 1 to 8 carbon atoms, the cycloalkyl group having 3 to 8 carbon atoms, and the phenyl group in R ¹ to R ⁴ may have a substituent. Examples of the substituent include a halogen atom, -R ⁷ , -OH, -OR ⁷ , -SO ₃ H, -SO ₃ M, -CO ₂ H, -CO ₂ R ⁷ , -SO ₃ R ⁷ , -SO ₂ NHR ⁸ , -SO ₂ NR ⁸ R ⁹ , -SO ₃ ^- , and the like.

Here, R ⁷ represents a saturated hydrocarbon group having 1 to 10 carbon atoms. However, the hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom, and the methylene group contained in the saturated hydrocarbon group may be replaced with an oxygen atom, a carbonyl group or -NR ⁷ -.

R ⁸ and R ⁹ independently represent a linear or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms (preferably 3 to 8 carbon atoms) or -G, or R ⁸ and R ⁹ Represents a heterocyclic group having 2 to 10 carbon atoms formed by bonding to each other. The hydrogen atom contained in the alkyl group and the cycloalkyl group may be substituted with a hydroxyl group, a halogen atom, -G, -CH = CH ₂ or -CH = CHR ⁷ , and the methylene group contained in the alkyl group and the cycloalkyl group may be an oxygen atom , A carbonyl group or -NR ⁷ -, and the hydrogen atom contained in the heterocyclic group may be substituted with -R ⁷ , -OH or -G.

M represents a sodium atom or a potassium atom.

G represents an aromatic hydrocarbon group having 6 to 10 carbon atoms or an aromatic heterocyclic group having 5 to 10 carbon atoms. However, the hydrogen atoms contained in the aromatic hydrocarbon group and aromatic heterocyclic group may be substituted with ^{-OH, -R 7, -OR 7,} -NO 2, -CH = CH 2, -CH = CHR 7 , or a halogen atom.

The saturated hydrocarbon group in R ⁷ has 1 to 10 carbon atoms, and may be any of linear, branched and cyclic, and may have a crosslinked structure. Specifically, in addition to the same alkyl groups as R ¹ to R ⁴ , there can be mentioned a nonyl group, a decanyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group and a tricyclodecanyl group. Examples of the group in which the methylene group contained in the saturated hydrocarbon group is substituted with an oxygen atom include a methoxypropyl group, an ethoxypropyl group, a 2-ethylhexyloxypropyl group, and a methoxyhexyl group.

Specific examples of -CO ₂ R ^{7 which} is a substituent of the alkyl group, cycloalkyl group and phenyl group in R ¹ to R ⁴ include a methyloxycarbonyl group, an ethyloxycarbonyl group, a propyloxycarbonyl group, an isopropyloxycarbonyl group, a butyloxycarbonyl group, A hexyloxycarbonyl group, and a methoxypropyloxycarbonyl group. Specific examples of -SO ₃ R ⁷ include a methanesulfonyl group, an ethanesulfonyl group, a hexanesulfonyl group and a decanesulfonyl group.

Specific examples of the heterocyclic group formed by combining R ⁸ and R ⁹ with each other include pyrrole, pyridine, indole, isoindole, quinoline, isoquinoline, carbazole, phenanthridine, acridine and phenothiazine.

Specific examples of the aromatic hydrocarbon group in G include a phenyl group, a naphthyl group and an azulenyl group. Specific examples of the aromatic heterocyclic group include furyl, thienyl, pyridyl, pyrrolyl, oxazolyl, isoxazol, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, .

Examples of the alkyl group having 1 to 8 carbon atoms in R ⁵ and R ⁶ include the same groups as described above.

r is an integer of 1 to 5, and when r is an integer of 2 or more, a plurality of R ^a may be the same or different, and r is preferably 1 or 2, and more preferably 1.

As the present coloring agent in the present invention, a coloring agent having a structure represented by the following formula (2) can be more preferably used. The -COOR ^b group in the formula (2) is preferably substituted at the o-position on the benzene ring.

In Formula (2),

R ^b represents a group having a polymerizable unsaturated group,

R ¹ to R ⁶ is R ¹ to R ⁶ and consent for Formula (1) Im;

As the group having a polymerizable unsaturated group in R ^b , the same groups as described above can be given. As the polymerizable unsaturated group in the present invention, a (meth) acryloyl group can be preferably used because of the ease of crosslinking reaction. As a preferable specific example of R ^b , there may be mentioned a group represented by the following formula (2a) or (2b).

[In the formulas (2a) and (2b)

R ¹⁰ and R ¹¹ independently represent a hydrogen atom or a methyl group,

Y ¹ , Y ² , Y ³ and Y ⁴ independently represent a substituted or unsubstituted alkanediyl group having 1 to 12 carbon atoms,

Z represents a -CO- group or a -COO- (*) group (* represents a bond with Y ² )

Q represents a divalent alicyclic hydrocarbon group,

p ¹ represents an integer of 0 to 12,

p ² and p ³ independently represent an integer of 0 to 6;

R ¹⁰ and R ¹¹ are preferably a hydrogen atom and a methyl group in the methyl group.

Examples of the alkanediyl group having 1 to 12 carbon atoms represented by Y ¹ to Y ⁴ include a methylene group, an ethylene group, an ethane-1,1-diyl group, a propane-1,1-diyl group, Propane-1,3-diyl group, propane-2,2-diyl group, butane-1,2-diyl group, butane-1,3-diyl group, butane- Diyl group, a pentane-1,3-diyl group, a pentane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,5-diyl group, A 1,8-diyl group, a decane-1,10-diyl group and the like. Among them, an alkanediyl group having 2 to 8 carbon atoms is preferable, and an alkanediyl group having 2 to 6 carbon atoms is more preferable. Examples of the substituent of the alkanediyl group include a hydroxyl group, a halogen atom, a (meth) acryloyloxy group, and a phenoxy group. Among them, a hydroxyl group is preferable.

As the divalent alicyclic hydrocarbon group for Q, an alicyclic hydrocarbon group having 3 to 20 carbon atoms is preferable, and an alicyclic hydrocarbon group having 3 to 12 carbon atoms is more preferable. Further, the alicyclic hydrocarbon group may be a 2 to 4-membered bridged cyclic hydrocarbon group.

As R ^{b, a} (meth) acryloyloxyalkyl group is preferable. The total number of carbon atoms of the (meth) acryloyloxyalkyl group is preferably 4 to 16, more preferably 4 to 10.

p ¹ is preferably an integer of 0 to 3, and p ² and p ³ are preferably an integer of 0 to 3 independently of each other.

The colorant having the structure represented by the formula (2) can be obtained, for example, by an esterification reaction between a compound represented by the following formula (3) and a compound having a hydroxyl group and a (meth) acryloyl group. As the esterification reaction, a known method can be applied. The -COOH group in the formula (3) is preferably substituted at the o-position on the benzene ring.

[In the formula (3)

R ¹ to R ⁶ is R ¹ to R ⁶ and consent for Formula (1),

X ^- represents an anion]

The compound having a hydroxyl group and a (meth) acryloyl group may have at least one hydroxyl group and at least one (meth) acryloyl group in the compound, and the number of the bond and the bonding position of the hydroxyl group and the (meth) . As the hydroxyl group, any of an alcoholic hydroxyl group and a phenolic hydroxyl group can be used. In addition, in the case of having a substituent other than the hydroxyl group and the (meth) acryloyl group, the kind, bonding position, and bonding number thereof are not limited.

Examples of the compound having a preferred hydroxyl group and (meth) acryloyl group include compounds represented by the following formula (3a) or (3b).

R ¹⁰ , R ¹¹ , Y ¹ , Y ² , Y ³ , Y ⁴ , Z, Q, p ¹ , p ² and p ³ are the same as those in the formulas (3a) and (3b)

More specific examples of the compound having a hydroxyl group and a (meth) acryloyl group include compounds represented by the following formulas (2-1) to (2-4).

[In the formula (2-1), "

R ¹² represents a hydrogen atom or a methyl group,

a and b independently represent an integer of 0 to 2,

c represents an integer of 1 to 6,

Provided that at least one group selected from a and b is an integer of 1 or more, -CH (OH) - group, -CH (CH ₃ ) - group and -CH ₂ - group may be bonded in any order]

In the formula (2-2)

R ¹³ represents a hydrogen atom or a methyl group,

d and e independently represent an integer of 1 to 12;

[In the formula (2-3), R ¹⁴ represents a hydrogen atom or a methyl group,

f and g independently represent an integer of 1 to 12;

[In the formula (2-4)

R ¹⁵ represents a hydrogen atom or a methyl group,

W represents a divalent group selected from the group of groups represented by the following formulas (I) to (IV)

h and i independently represent an integer of 0 to 6;

Examples of the compound represented by the general formula (2-1) include (meth) acrylic acid 2-hydroxyethyl ester, (meth) acrylic acid 1-methyl-2-hydroxyethyl ester, (meth) (Meth) acrylate, 5-hydroxypentyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 1-glycerol (Meth) acrylate, 9-hydroxyhexyl (meth) acrylate, 8-hydroxyoctyl (meth) acrylate, 9-hydroxynonyl Ester, (meth) acrylic acid 11-hydroxydecyl ester, and (meth) acrylic acid 12-hydroxydodecyl ester.

Examples of the compound represented by the general formula (2-2) include (meth) acrylic acid 2- (6-hydroxyhexanoyloxy) ethyl ester, (meth) acrylic acid 3- (6-hydroxyhexanoyloxy) (Meth) acrylate, (meth) acrylic acid 4- (6-hydroxyhexanoyloxy) butyl ester, (meth) (Meth) acrylic acid (6-hydroxyhexanoyloxy) alkyl esters, such as (meth) acrylic acid (6-hydroxyhexanoyloxy) And PLACCEL FM1D and PLACCEL FM2D (manufactured by Daicel Chemical Industries, Ltd.).

Examples of the compound represented by formula (2-3) include (meth) acrylic acid 2- (3-hydroxy-2,2-dimethylpropoxycarbonyloxy) ethyl ester, (meth) (Meth) acrylic acid 4- (3-hydroxy-2,2-dimethylpropoxycarbonyloxy) butyl ester, (meth) acrylic acid 5 (Meth) acrylate such as (meth) acrylic acid 6- (3-hydroxy-2,2-dimethylpropoxycarbonyloxy) pentyl ester, (3-hydroxy-2,2-dimethylpropoxycarbonyloxy) alkyl esters such as (meth) acrylic acid (3-hydroxy-2,2-dimethylpropoxycarbonyloxy) Commercially available products of esters include trade name HEMAC1 (manufactured by Daicel Chemical Industries, Ltd.).

Examples of the compound represented by the formula (2-4) include 4-hydroxycyclohexyl methacrylate, (meth) acrylic acid (4-hydroxymethylcyclohexyl) methyl ester, (meth) Hydroxycyclohexyl [2.2.1] hept-5-en-2-yl ester, (meth) acrylic acid (3-hydroxycyclohexyl) ethyl ester, (Meth) acrylic acid 2- [3- (2-hydroxyethyl) bicyclo [2.2.1] hept-5-en-2-yl) 2-yl] ethyl ester, (meth) acrylic acid 8-hydroxybicyclo [2.2.1] hept-5-en-2-yl ester, (meth) acrylic acid 2-hydroxyoctahydro- (Meth) acrylic acid (2-hydroxymethyloctahydro-4,7-methanoinden-5-yl) methyl ester, 2- (2- Ethyl) octahydro-4,7-methanoinden-5-yl] ethyl ester, (meth) acrylic acid 3- (Meth) acrylic acid (3-hydroxymethyladamantan-1-yl) methyl ester, 2- (3- (2-hydroxyethyl) adamantan- 1-yl] ethyl ester, and the like.

Among these compounds having a hydroxyl group and a (meth) acryloyl group, from the viewpoint of reactivity

1) a compound wherein a and b in the formula (2-1) are 0 and c is 2 to 6,

2) a compound of the formula (2-1) wherein a is 1, b is 0, and c is 1 to 5,

3) a compound wherein d in the formula (2-2) is 2 or 3 and e is 1,

4) a compound wherein f in the formula (2-3) is 2 or 3 and g is 1,

5) a compound of the formula (2-4) wherein h is 1 or 2 or i is 1 or 2 and W is a group represented by the formula (I) or (IV)

Etc. are preferable.

Among them, (meth) acrylic acid 2-hydroxyethyl ester, (meth) acrylic acid 1-glycerol, (meth) acrylic acid 6-hydroxyhexyl ester, (Meth) acrylic acid (3-hydroxy-2,2-dimethylpropoxycarbonyloxy) ethyl ester, (meth) acrylic acid (4-hydroxymethylcyclohexyl) methyl ester, Methylimidazol-1-yl) methyl ester, and the like.

Examples of the compound having a hydroxyl group and a (meth) acryloyl group other than the compounds represented by the general formulas (2-1) to (2-4) include 4-hydroxyphenyl (meth) acrylate, pentaerythritol tri (meth) , Dipentaerythritol penta (meth) acrylate, glycerol dimethacrylate, and compounds represented by the following group a.

In the present invention, the compounds having a hydroxyl group and a (meth) acryloyl group may be used alone or in combination of two or more.

Compound group a

Next, X ^- in the above formula (3) will be explained.

X ^- is not particularly restricted but includes, for example, a halogen ion, a boron anion, a phosphate anion, carboxylic acid anion, sulfuric acid anion, an organic acid anion, a nitrogen anion, methide anion.

Examples of the halogen ion include a fluoride ion, a chloride ion, a bromide ion, and an iodide ion.

Examples of the boron anion include an inorganic boron anion such as BF ₄ ^- ;

^{_{(CF 3) 4 B -,}} (CF 3) 3 BF -, (CF 3) 2 BF 2 -, (CF 3) BF 3 -, (C 2 F 5) 4 B -, (C 2 F 5) 3 _{^{BF -, (C 2 F 5}} ) BF 3 -, (C 2 F 5) 2 BF 2 -, (CF 3) (C 2 F 5) 2 BF -, (C 6 F 5) 4 B, [(CF _{3) 2 C 6 H 3]} 4 B -, (CF 3 C 6 H 4) 4 B -, (C 6 F 5) 2 BF 2 -, (C 6 F 5) BF 3, (C 6 H 3 F ^{_{2) 4 B -, B (}} CN) 4 -, B (CN) F 3 -, B (CN) 2 F 2 -, B (CN) 3 F -, (CF 3) 3 B (CN) -, ( _{CF 3) 2 B (CN)} 2 -, (C 2 F 5) 3 B (CN) -, (C 2 F 5) 2 B (CN) 2 -, (nC 3 F 7) 3 B (CN) - _{, (nC 4 F 9) 3} B (CN) -, (nC 4 F 9) 2 B (CN) 2 -, (nC 6 F 13) 3 B (CN) -, (CHF 2) 3 B (CN) _{^{-, (CHF 2) 2 B}} (CN) 2 -, (CH 2 CF 3) 3 B (CN) -, (CH 2 CF 3) 2 B (CN) 2 -, (CH 2 C 2 F 5) 3 ^{B (CN) -, (CH} 2 C 2 F 5) 2 B (CN) 2 -, (CH 2 CH 2 C 3 F 7) 2 B (CN) 2 -, (nC 3 F 7 CH 2) 2 B (CN) ₂ ^- , (C ₆ H ₅ ) ₃ B (CN) ^- , tetraphenyl borate, tetrakis (monofluorophenyl) borate, tetrakis (difluorophenyl) borate, tetrakis ) Borate, tetrakis ( Tetrafluorophenyl) borate, tetrakis (pentafluorophenyl) borate, tetrakis (tetrafluorophenyl) borate, tetra (tolyl) In addition to organoboron anions such as [tris (pentafluorophenyl) phenyl] borate and tridecahydride-7,8-dicarbal undecaborate, in addition to the organic boron anions described in JP-A 10-195119, Boron anions described in JP-A-2010-094807, JP-A-2006-243594, JP-A-2002-341533, JP-A-08-015521, etc.

Examples of the phosphate anion include inorganic phosphate anions such as HPO ₄ ^{2 -} , PO ₄ ^{3 -} , and PF ₆ ^- ;

_{(C 2 F 5) 2 PF} 4 -, (C 2 F 5) 3 PF 3 -, [(CF 3) 2 CF] 2 PF 4 -, [(CF 3) 2 CF] 3 PF 3, (nC 3 ^{_{F 7) 2 PF 4 -,}} (nC 3 F 7) 3 PF 3 -, (nC 4 F 9) 3 PF 3 -, (C 2 F 5) (CF 3) 2 PF 3 -, [(CF 3) ^{_{2 CFCF 2] 2 PF 4 -}} , [(CF 3) 2 CFCF 2] 3 PF 3 -, (nC 4 F 9) 2 PF 4 -, (nC 4 F 9) 3 PF 3 -, (C 2 F 4 _{H) (CF 3) 2 PF} 3 -, (C 2 F 3 H 2) 3 PF 3 -, (C 2 F 5) (CF 3) 2 PF 3 -, octyl phosphate anion, a dodecyl phosphate anion, an octadecyl And organic phosphate anions such as phosphate anion, phenyl phosphate anion and nonylphenyl phosphate anion.

Examples of the carboxylic acid anion include CH ₃ COO ^- , C ₂ H ₅ COO ^- , C ₆ H ₅ COO ^- and the like, as well as JP-A-2009-265641 and JP-A 2008-096680 Of carboxylic acid anions.

Examples of the sulfuric acid anion include sulfuric acid anion and sulfurous acid anion.

Examples of the organic sulfonic acid anion include alkylsulfonic acid anions such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid and nonafluorobutanesulfonic acid;

(Meth) acryloyloxy-carbonates other than the arylsulfonic acid anions such as benzenesulfonic acid, benzene disulfonic acid, p-toluenesulfonic acid, p-trifluoromethylsulfonic acid, pentafluorobenzenesulfonic acid, naphthalenesulfonic acid, 1,1,2,2-tetrafluoroethanesulfonic acid, 2- (4-vinylphenyloxy) -1,1,2,2-tetrafluoroethanesulfonic acid, International Publication No. 2011/037195, 3736221, and the organic sulfonic acid anions described in Japanese Patent Application Laid-Open No. 2011-070172.

Further, for example, as nitrogen anion ^{_{[(CN) 2 N] -}} , [(FSO 2) 2 N] -, [(FSO 2) N (CF 3 SO 2)] -, [(CF 3 SO 2) 2 _{^{N] -, [(FSO 2}} ) N (CF 3 CF 2 SO 2)] -, [(FSO 2) N {(CF 3) 2 CFSO 2}] -, [(FSO 2) N (CF 3 CF 2 ^{_{CF 2 SO 2)] -,}} [(FSO 2) N (CF 3 CF 2 CF 2 CF 2 SO 2)] -, [(FSO 2) N {(CF 3) 2 CFCF 2 SO 2}] -, [ (FSO ₂ ) N {CF ₃ CF ₂ (CF ₃ ) CFSO ₂ }] ^- , [(FSO ₂ ) N {(CF ₃ ) ₃ CSO ₂ }] ^- And a nitrogen anion described in Japanese Patent Application Laid-Open No. 11-116803 and Japanese Patent Application Laid-Open No. 2010-090341.

Further, for example, as methide anion _{(CF 3 SO 2) 3 C} -, (CF 3 CF 2 SO 2) 3 C -, [(CF 3) 2 CFSO 2] 3 C -, (CF 3 CF 2 CF ^{_{2 SO 2) 3 C -,}} (CF 3 CF 2 CF 2 CF 2 SO 2) 3 C -, [(CF 3) 2 CFCF 2 SO 2] 3 C -, [CF 3 CF 2 (CF 3) CFSO 2 ] ₃ C ^- , [(CF ₃ ) ₃ CSO ₂ ] ₃ C ^- , (FSO ₂ ) ₃ C ^-, and the like, as well as Japanese Patent Laid-Open Publication No. 2011-145540, US Patent No. 5,554,664, 309408, 2004-085657, and 2010-505787, and the like.

The present colorant may also be a xanthan-based lake pigment having a polymerizable unsaturated group in a color developing part. Examples of the precipitant include barium chloride, calcium chloride, ammonium sulfate, aluminum chloride, aluminum acetate, lead acetate, tannic acid, catanol, tamol, and complex acid as the precipitating agent. (Phosphotungstic acid, phosphomolybdic acid, phosphotungstic molybdic acid, silico tungsten molybdic acid, silico tungstic acid, silicomolybdic acid, tungsten molybdic acid, tungstic acid, and phosphorus molybdic acid), which are referred to as complex heteropoly acids . The present coloring agent in the form of a lake pigment can be produced, for example, by laking a compound obtained by the esterification reaction between the compound represented by the above formula (3) and a compound having a hydroxyl group and a (meth) acryloyl group with a precipitant have.

The coloring composition of the present invention may further contain other coloring agents together with the present coloring agent as a coloring agent. The other colorants are not particularly limited, and the color and the material can be appropriately selected depending on the application.

As the other colorants, pigments other than the present colorant, dyes other than the present colorant, and natural pigments can be used, and organic pigments and organic dyes are preferable in terms of obtaining pixels having high brightness and color purity.

As the organic pigment, for example, a compound classified as a pigment in the color index (published by C. I. The Society of Dyers and Colourists), that is, a color index (C.I.

CI Pigment Red 1, CI Pigment Red 2, CI Pigment Red 5, CI Pigment Red 17, CI Pigment Red 31, CI Pigment Red 32, CI Pigment Red 41, CI Pigment Red 48: CI Pigment Red 48: 3, CI Pigment Red 48: 4, CI Pigment Red 48: 5, CI Pigment Red 49, CI Pigment Red 49: 1, CI Pigment Red CI Pigment Red 52: 1, CI Pigment Red 52: 2, CI Pigment Red 53: 1, CI Pigment Red 54, CI Pigment Red 57: CI Pigment Red 58, CI Pigment Red 58: 1, CI Pigment Red 58: 2, CI Pigment Red 58: 3, CI Pigment Red 58: 63, CI Pigment Red 63: 1, CI Pigment Red 63: 2, CI Pigment Red 63: 3, CI Pigment Red 64: I. Pigment Red 68, CI Pigment Red 81, CI Pigment Red 81: 1, CI Pigment Red 122, CI Pigment Red 123, CI Pigment Red 144, CI Pigment Red 149, CI Pigment Red 166, CI Pigment Red 168, CI Pigment Red 170, CI Pigment Red 171, CI Pigment Red 175, CI Pigment Red 176, CI Pigment Red 177, CI Pigment Red 178, CI Pigment Red 179, CI Pigment Red 180, CI Pigment Red 185, CI Pigment Red 187, CI Pigment Red 200, CI Pigment Red 202, CI Pigment Red 206, CI Pigment Red 207, CI Pigment Red 209, CI Pigment Red 233, CI Pigment Red 242, CI Pigment Red 243, CI Pigment Red 234, CI Pigment Red 237, CI Pigment Red 242, CI Pigment Red 243, Pigment Red 247, C. I. Pigment Red 254, C. I. Pigment Red 255, C. I. Pigment Red 262, C. I. Pigment Red 264, C. I. Pigment red pigments such as red 272;

CI Pigment Violet 1, CI Pigment Violet 2, CI Pigment Violet 3, CI Pigment Violet 3: 1, CI Pigment Violet 3: 3, CI Pigment Violet 19, CI Pigment Violet 23, CI Pigment Violet 3, 27, CI Pigment Violet 29, CI Pigment Violet 32, CI Pigment Violet 36, CI Pigment Violet 38, CI Pigment Violet 39;

CI Pigment Blue 1, CI Pigment Blue 2, CI Pigment Blue 3, CI Pigment Blue 9, CI Pigment Blue 10, CI Pigment Blue 14, CI Pigment Blue 15, CI Pigment Blue 15: 3, CI Pigment Blue 15: 4, CI Pigment Blue 15: 6, CI Pigment Blue 17: 1, CI Pigment Blue 24, CI Pigment Blue 24: 1, CI Pigment Blue 56, CI Pigment Blue 60, CI Pigment Blue 61, CI Pigment Blue 62, CI Pigment Blue 80 and the like.

In the present invention, when using a pigment as another colorant, the pigment may be purified by recrystallization, reprecipitation, solvent washing, sublimation, vacuum heating, or a combination thereof. Further, the pigment may be used by modifying its particle surface with a resin as necessary. As the resin for modifying the particle surface of the pigment, for example, a vehicle resin described in Japanese Patent Application Laid-Open No. 2001-108817 or a commercially available resin for dispersing various pigments may be mentioned. The organic pigment is preferably used by finely grinding primary particles by so-called salt milling. As a method of the salt milling, for example, a method disclosed in Japanese Unexamined Patent Application Publication No. 08-179111 can be adopted.

In the present invention, when a pigment is used as the other coloring agent, a known dispersing agent and a dispersion auxiliary agent may be further contained. Examples of the known dispersant include urethane dispersant, polyethyleneimine dispersant, polyoxyethylene alkyl ether dispersant, polyoxyethylene alkyl phenyl ether dispersant, polyethylene glycol diester dispersant, sorbitan fatty acid ester dispersant, polyester dispersant , An acrylic dispersant and the like, and as a dispersing aid, a pigment derivative and the like.

Dispersing agents such as Disperbyk-2000, Disperbyk-2001, BYK-LPN6919, BYK-LPN21116 and BYK-LPN21324 (manufactured by BYK) are commercially available, Disperbyk-161, Disperbyk-162, Disperbyk-165, Disperbyk-167, Disperbyk-170 and Disperbyk-182 (manufactured by BYK) ) And the like were used as a polyethylene imine dispersant, and Sorbus 24000 (manufactured by Rubriez Co., Ltd.) and the like as a polyethyleneimine dispersant were used. Manufactured by Kabushiki Kaisha), and the like.

Specific examples of the pigment derivative include copper phthalocyanine, diketopyrrolopyrrole, and sulfonic acid derivatives of quinophthalone.

As organic dyes, the following organic dyes may be preferably used among those having the color index (C.I.) name attached thereto.

For example,

Red dyes such as C. I. Solvent Red 45, C. I. Solvent Red 49;

C. I. Solvent Blue 35, C. I. Solvent Blue 37, C. I. Solvent Blue 59, C. I. Solvent Blue 67;

Acidic red dyes such as C. I. Acid Red 91, C. I. Acid Red 92, C. I. Acid Red 97, C. I. Acid Red 114, C. I. Acid Red 138, C. I. Acid Red 151 and the like;

Acid blue dyes such as C. I. Acid Blue 80, C. I. Acid Blue 83, C. I. Acid Blue 90 and the like.

The coloring composition of the present invention is preferably used for forming a red pixel or a blue pixel. When used for forming red pixels, it is preferable that (A) the coloring agent contains at least one coloring agent selected from the group consisting of a red coloring agent and a purple coloring agent as another coloring agent together with the present coloring agent. On the other hand, when used for forming blue pixels, it is preferable that (A) the colorant contains at least one coloring agent selected from the group consisting of a blue coloring agent and a purple coloring agent as other coloring agents. Examples of the red coloring agent include the above-mentioned red pigment, red dye and acidic red dye. Of these, C.I. Pigment Red 177, C.I. Pigment Red 242, C.I. Pigment Red 254 and the like are preferable. As the violet colorant, the above-mentioned violet pigments can be exemplified. Among them, C. I. Pigment Violet 23 is preferable. Examples of the blue colorant include C.I. Pigment Blue 1, C.I. Pigment Blue 15: 6 and the like, among which the blue pigments, blue dyes and acid blue dyes described above are preferable.

In the present invention, the other colorants may be used alone or in combination of two or more.

The content ratio of the (A) coloring agent is usually from 5 to 70% by mass, preferably from 5 to 60% by mass, based on the solid content of the coloring composition, from the viewpoint of forming a pixel having excellent brightness and excellent color purity or a black matrix having excellent light- The solid content referred to herein is a component other than the solvent described below.

(B) binder resin

The binder resin (B) in the present invention is not particularly limited, but is preferably a resin having an acidic functional group such as a carboxyl group or a phenolic hydroxyl group. Among them, a polymer having a carboxyl group (hereinafter also referred to as a " carboxyl group-containing polymer ") is preferable. For example, an ethylenically unsaturated monomer having at least one carboxyl group (hereinafter also referred to as " unsaturated monomer (b1) (Hereinafter also referred to as " unsaturated monomer (b2) ").

Examples of the unsaturated monomer (b1) include mono [2- (meth) acryloyloxyethyl], [omega] -carboxypolycaprolactone mono (meth) acrylate, maleic anhydride, p-vinylbenzoic acid and the like.

These unsaturated monomers (b1) can be used individually or in mixture of 2 or more types.

As the unsaturated monomer (b2), for example,

N-substituted maleimide such as N-phenylmaleimide, N-cyclohexylmaleimide;

Aromatic vinyl compounds such as styrene,? -Methylstyrene, p-hydroxystyrene, p-hydroxy-? -Methylstyrene, p-vinylbenzyl glycidyl ether and acenaphthylene;

Acrylates such as methyl (meth) acrylate, n-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, 2-hydroxyethyl (meth) (Meth) acrylate, polyethylene glycol (having a degree of polymerization of 2 to 10) methyl ether (meth) acrylate, polypropylene glycol (having a degree of polymerization of 2 to 10) (Meth) acrylate, isobornyl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decan-8-yl (meth) acrylate, propylene glycol (Meth) acrylate, dicyclopentenyl (meth) acrylate, glycerol mono (meth) acrylate, 4-hydroxyphenyl (meth) acrylate, ethylene oxide- ) Acrylate, 3,4- Acrylate such as (meth) acryloyloxymethyl] -3-ethyloxetane, 3 - [(meth) acryloyloxymethyl] oxetane, 3 - [(meth) acryloyloxymethyl] ;

Cyclohexyl vinyl ether, isobornyl vinyl ether, tricyclo [5.2.1.0 ^2,6 ] decan-8-yl vinyl ether, pentacyclopentadecanyl vinyl ether, 3- (vinyloxymethyl) Vinyl ethers such as;

And a macromonomer having a mono (meth) acryloyl group at the end of a polymer molecular chain such as polystyrene, polymethyl (meth) acrylate, poly-n-butyl (meth) acrylate and polysiloxane.

These unsaturated monomers (b2) can be used individually or in mixture of 2 or more types.

In the copolymer of the unsaturated monomer (b1) and the unsaturated monomer (b2), the copolymerization ratio of the unsaturated monomer (b1) in the copolymer is preferably 5 to 50% by mass, more preferably 10 to 40% by mass. By copolymerizing the unsaturated monomer (b1) in such a range, a colored composition excellent in alkali developability and storage stability can be obtained.

Specific examples of the copolymer of the unsaturated monomer (b1) and the unsaturated monomer (b2) include those described in JP-A-7-140654, JP-A-8-259876, 10-31308, 10-300922, 11-174224, 11-258415, 2000-56118, etc., as disclosed in Japanese Patent Application Laid- And Japanese Patent Application Laid-Open No. 2004-101728 and the like.

Further, in the present invention, for example, Japanese Patent Application Laid-Open No. 5-19467, Japanese Patent Application Laid-Open No. 6-230212, Japanese Patent Application Laid-Open No. 7-207211, (Meth) acryloyl group in the side chain as disclosed in Japanese Patent Application Laid-Open Nos. 09-325494, 11-140144 and 2008-181095, The carboxyl group-containing polymer may be used as a binder resin.

The binder resin in the present invention has a weight average molecular weight (Mw) in terms of polystyrene measured by gel permeation chromatography (hereinafter abbreviated as GPC) (elution solvent: tetrahydrofuran), usually 1,000 to 100,000, preferably 3,000. To 50,000. If the Mw is too small, the residual film ratio of the resulting film may deteriorate, the pattern shape, heat resistance, and the like may deteriorate or the electrical characteristics may deteriorate. On the other hand, if the Mw is too large, There is a possibility that dry foreign matter tends to be generated at the time of application by the coating method.

The ratio (Mw / Mn) of the weight average molecular weight (Mw) to the number average molecular weight (Mn) of the binder resin in the present invention is preferably 1.0 to 5.0, more preferably 1.0 to 3.0. In addition, Mn here means the number average molecular weight of polystyrene conversion measured by GPC (elution solvent: tetrahydrofuran).

The binder resin in the present invention can be produced by a known method. For example, Japanese Unexamined Patent Application Publication No. 2003-222717, Japanese Patent Application Laid-Open No. 2006-259680, International Publication No. 07/029871 The structure, Mw, and Mw / Mn can also be controlled by the disclosed method.

In this invention, binder resin can be used individually or in mixture of 2 or more types.

The content of the binder resin in the present invention is generally 10 to 1,000 parts by mass, preferably 20 to 500 parts by mass, per 100 parts by mass of the (A) colorant. If the content of the binder resin is too small, for example, the alkaline developability may deteriorate or the storage stability of the resulting colored composition may deteriorate. On the other hand, when the content is too large, the concentration of the colorant relatively decreases, It may be difficult to achieve the above.

- (C) Crosslinking agent -

In the present invention, (C) a crosslinking agent means a compound having two or more polymerizable groups. Examples of the polymerizable group include an ethylenic unsaturated group, an oxiranyl group, an oxetanyl group, and an N-alkoxymethylamino group. In the present invention, as the crosslinking agent (C), a compound having two or more (meth) acryloyl groups or a compound having two or more N-alkoxymethylamino groups is preferable.

Specific examples of the compound having two or more (meth) acryloyl groups include a polyfunctional (meth) acrylate obtained by reacting an aliphatic polyhydroxy compound with (meth) acrylic acid, a polyfunctional (meth) acrylate modified with caprolactone, Polyfunctional urethane (meth) acrylate obtained by reacting (meth) acrylate having a hydroxyl group with a polyfunctional isocyanate, (meth) acrylate having a hydroxyl group and an acid anhydride having a hydroxyl group And a polyfunctional (meth) acrylate having a carboxyl group obtained by the reaction.

Examples of the aliphatic polyhydroxy compound include divalent aliphatic polyhydroxy compounds such as ethylene glycol, propylene glycol, polyethylene glycol and polypropylene glycol; And tri- or higher aliphatic polyhydroxy compounds such as glycerin, trimethylol propane, pentaerythritol and dipentaerythritol. Examples of the (meth) acrylate having a hydroxyl group include 2-hydroxyethyl (meth) acrylate, trimethylolpropane di (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta Methacrylate, and glycerol dimethacrylate. Examples of the polyfunctional isocyanate include tolylene diisocyanate, hexamethylene diisocyanate, diphenylmethylene diisocyanate, and isophorone diisocyanate. Examples of the acid anhydride include anhydrides of dibasic acids such as succinic anhydride, maleic anhydride, glutaric anhydride, itaconic anhydride, phthalic anhydride, hexahydrophthalic anhydride, anhydride pyromellitic acid, biphenyltetracarboxylic acid dianhydride , Benzophenone tetracarboxylic acid dianhydride, and the like.

Examples of the caprolactone-modified polyfunctional (meth) acrylate include compounds described in paragraphs [0015] to [0018] of JP-A No. 11-44955. Examples of the alkylene oxide-modified polyfunctional (meth) acrylate include at least one selected from bisphenol A di (meth) acrylate, ethylene oxide and propylene oxide modified with at least one selected from ethylene oxide and propylene oxide Trimethylol propane tri (meth) acrylate modified with at least one member selected from isocyanuric acid tri (meth) acrylate, ethylene oxide and propylene oxide modified with at least one member selected from the group consisting of ethylene oxide and propylene oxide At least one member selected from pentaerythritol tetra (meth) acrylate, ethylene oxide and propylene oxide modified with at least one member selected from pentaerythritol tri (meth) acrylate, ethylene oxide and propylene oxide, By The dipentaerythritol, and the like erythritol penta (meth) acrylate, and ethylene oxide-modified by means of at least one member selected from propylene oxide, dipentaerythritol hexa (meth) acrylate.

Examples of the compound having two or more N-alkoxymethylamino groups include compounds having a melamine structure, a benzoguanamine structure, and a urea structure. Also, the melamine structure and the benzoguanamine structure refer to chemical structures having one or more triazine rings or phenyl-substituted triazine rings as basic skeletons, and also include melamine, benzoguanamine, or condensates thereof. Specific examples of the compound having two or more N-alkoxymethylamino groups include N, N, N ', N', N ", N" -hexa (alkoxymethyl) melamine, N, N, N ', N'-tetra (alkoxy Methyl) benzoguanamine, N, N, N ', N'- tetra (alkoxy methyl) glycoluril, etc. are mentioned.

(Meth) acrylate, caprolactone-modified polyfunctional (meth) acrylate, polyfunctional urethane (meth) acrylate and carboxyl group obtained by reacting a tri- or higher valent aliphatic polyhydroxy compound with (meth) N, N ', N', N ', N "-hexa (alkoxymethyl) melamine, N, N, N', N'-tetra (alkoxymethyl) benzoguanamine Nammin is preferable. Among the multifunctional (meth) acrylates obtained by reacting a trivalent or higher aliphatic polyhydroxy compound with (meth) acrylic acid, trimethylolpropane triacrylate, pentaerythritol triacrylate, dipentaerythritol pentaacrylate, Among the polyfunctional (meth) acrylates having a carboxyl group, a compound obtained by reacting pentaerythritol triacrylate with succinic anhydride, a compound obtained by reacting dipentaerythritol pentaacrylate with succinic anhydride, , The strength of the colored layer is high, the surface smoothness of the colored layer is excellent, and it is difficult to cause background contamination or film residue on the substrate of the unexposed portion and on the light-shielding layer.

In the present invention, the crosslinking agent (C) may be used alone or as a mixture of two or more thereof.

The content of the crosslinking agent (C) in the present invention is preferably from 10 to 1,000 parts by mass, more preferably from 20 to 500 parts by mass, per 100 parts by mass of the colorant (A). In this case, if the content of the cross-linking agent is too small, there is a possibility that sufficient curability is not obtained. On the other hand, when the content of the crosslinking agent is too large, when the alkali developing property is imparted to the coloring composition of the present invention, the alkaline developing property is lowered, and the substrate contamination or film residue on the light- There is a tendency.

Photoinitiator

The coloring composition of this invention can be made to contain a photoinitiator. Thereby, the coloring composition can be imparted with radiation sensitivity. The photopolymerization initiator used in the present invention is a compound which generates active species capable of initiating polymerization of (C) a crosslinking agent by exposure to radiation such as visible light, ultraviolet light, deep ultraviolet light, electron beam, and X-ray.

Examples of such photopolymerization initiators include thioxanone compounds, acetophenone compounds, nonimidazole compounds, triazine compounds, O-acyloxime compounds, onium salt compounds, benzoin compounds, benzophenone compounds, -Diketone compounds, polynuclear quinone compounds, diazo compounds, imidosulfonate compounds, onium salt compounds and the like.

In this invention, a photoinitiator can be used individually or in mixture of 2 or more types. As the photopolymerization initiator, at least one member selected from the group consisting of a thioxanone compound, an acetophenone compound, a nonimidazole compound, a triazine compound, and an O-acyloxime compound is preferable.

Specific examples of the thioxanone compound in the photopolymerization initiator of the present invention include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2-isopropylthioxanthone, 4-isopropylthioxanthone , 2,4-dichlorothioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone and 2,4-diisopropylthioxanthone.

Specific examples of the acetophenone-based compound include 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane-1-one and 2-benzyl-2-dimethylamino-1- (4 -Morpholinophenyl) butan-1-one, 2- (4-methylbenzyl) -2- (dimethylamino) -1- (4-morpholinophenyl) butan-1-one, and the like.

Further, specific examples of the biimidazole compound include 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole, 2,2' -Bis (2,4-dichlorophenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis (2,4,6-trichlorophenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole etc. are mentioned.

When a nonimidazole-based compound is used as a photopolymerization initiator, it is preferable to use a hydrogen donor in combination because it can improve the sensitivity. As used herein, the term " hydrogen donor " means a compound capable of donating a hydrogen atom to a radical generated from a nonimidazole compound by exposure. Examples of the hydrogen donor include a mercaptan-based hydrogen donor such as 2-mercaptobenzothiazole and 2-mercaptobenzoxazole; And amine hydrogen donors such as 4,4'-bis (dimethylamino) benzophenone and 4,4'-bis (diethylamino) benzophenone. In the present invention, the hydrogen donors may be used singly or in combination of two or more. It is preferable that the combination of at least one mercaptan-based hydrogen donor and at least one amine-based hydrogen donor is used to improve the sensitivity .

In addition, specific examples of the triazine-based compound include 2,4,6-tris (trichloromethyl) -s-triazine, 2-methyl-4,6-bis (trichloromethyl) -s-triazine, 2- [ 2- (5-methylfuran-2-yl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- [2- (furan-2-yl) ethenyl] -4, 6-bis (trichloromethyl) -s-triazine, 2- [2- (4-diethylamino-2-methylphenyl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- [2- (3,4-dimethoxyphenyl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- (4-methoxyphenyl) -4,6-bis ( Trichloromethyl) -s-triazine, 2- (4-ethoxystyryl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4-n-butoxyphenyl) -4 Triazine type compounds which have halomethyl groups, such as a 6-bis (trichloromethyl) -s-triazine, are mentioned.

Specific examples of the O-acyloxime compound include 1,2-octanedione, 1- [4- (phenylthio) phenyl] -, 2- (O- benzoyloxime), ethanone, 1- [ (2-methylbenzoyl) -9H-carbazol-3-yl] -, 1- (O-acetyloxime), ethanone, 1- [ Yl) -, 1- (O-acetyloxime), ethanone, 1- [9-ethyl-6- { Dimethyl-1,3-dioxoranyl) methoxybenzoyl} -9H-carbazol-3-yl] -, 1- (O-acetyloxime). As commercially available products of O-acyloxime compounds, NCI-831 and NCI-930 (manufactured by ADEKA) may be used.

In the present invention, when a photopolymerization initiator other than a non-imidazole-based compound such as an acetophenone-based compound is used, a sensitizer may be used in combination. Examples of such sensitizers include 4,4'-bis (dimethylamino) benzophenone, 4,4'-bis (diethylamino) benzophenone, 4-diethylaminoacetophenone, Dimethylaminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoate, 2,5-bis (4-diethylaminobenzal) cyclohexanone, 7-diethylamino- 3- Coumarin, and 4- (diethylamino) chalcone.

In the present invention, the content of the photopolymerization initiator is preferably 0.01 to 120 parts by mass, particularly preferably 1 to 100 parts by mass, per 100 parts by mass of the (C) crosslinking agent. In this case, if the content of the photopolymerization initiator is too small, the curing by exposure may become insufficient, while if it is excessively large, the formed colored layer tends to fall off from the substrate at the time of development.

-menstruum-

The coloring composition of this invention contains the said (A)-(C) component and the other component added arbitrarily, Usually, a solvent is mix | blended and it is manufactured as a liquid composition. As the solvent, any of the components (A) to (C) and other components constituting the coloring composition may be appropriately selected and used as long as they are dispersed or dissolved and react with these components and have appropriate volatility.

As such a solvent, for example,

Ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono- -Propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono- Dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol mono-n-butyl ether, tripropylene glycol monomethyl ether, tri (Poly) alkylene glycol monoalkyl ethers such as propylene glycol monoethyl ether;

Lactic acid alkyl esters such as methyl lactate and ethyl lactate;

(Cyclo) alkyl alcohols such as methanol, ethanol, propanol, butanol, isopropanol, isobutanol, t-butanol, octanol, 2-ethylhexanol and cyclohexanol;

Ketoalcohols such as diacetone alcohol;

Ethylene glycol monomethyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, dipropylene glycol monomethyl ether (Poly) alkylene glycol monoalkyl ether acetates such as acetate, 3-methoxybutyl acetate and 3-methyl-3-methoxybutyl acetate;

Other ethers such as diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether and tetrahydrofuran;

Ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone and 3-heptanone;

Diacetates such as propylene glycol diacetate, 1,3-butylene glycol diacetate and 1,6-hexanediol diacetate;

Alkoxycarboxylates such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl ethoxyacetate and 3-methyl- Acid esters;

Ethyl acetate, n-propyl acetate, i-propyl acetate, n-butyl acetate, i-butyl acetate, n-amyl acetate, i-amyl acetate, n-butyl propionate, ethyl butyrate, n-propyl butyrate, i-propyl butyrate Other esters such as n-butyl butyrate, methyl pyruvate, ethyl pyruvate, n-propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, and ethyl 2-oxobutanoate;

Aromatic hydrocarbons such as toluene and xylene;

Amides or lactams such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and the like.

Propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, 3- (2-ethylhexyl) ethyl ether acetate, Methoxybutyl acetate, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, cyclohexanone, 2-heptanone, 3-heptanone, 1,3-butylene glycol diacetate, 1,6-hexanediol diacetate , Ethyl lactate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, 3-methyl-3-methoxybutyl propionate, n-butyl acetate, Amyl acetate, i-amyl acetate, n-butyl propionate, ethyl butyrate, i-propyl butyrate, n-butyl butyrate and ethyl pyruvate.

In this invention, a solvent can be used individually or in mixture of 2 or more types.

The content of the solvent is not particularly limited, but is preferably an amount such that the total concentration of each component except for the solvent of the coloring composition is 5 to 50 mass%, more preferably 10 to 40 mass%. By such an embodiment, it is possible to obtain a colorant dispersion having good dispersibility and stability, and a coloring composition having good applicability.

-additive-

The coloring composition of this invention may contain various additives as needed.

Examples of the additive include fillers such as glass and alumina; High molecular compounds such as polyvinyl alcohol and poly (fluoroalkyl acrylate); Surfactants such as fluorine-based surfactants and silicone-based surfactants; Vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) Aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (3,4-epoxycyclo Hexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane and the like Adhesion promoters; Antioxidants such as 2,2-thiobis (4-methyl-6-t-butylphenol) and 2,6-di-t-butylphenol; Ultraviolet absorbers such as 2- (3-t-butyl-5-methyl-2-hydroxyphenyl) -5-chlorobenzotriazole and alkoxybenzophenones; An anti-aggregation agent such as sodium polyacrylate; Amino-1-pentanol, 3-amino-1,2-propane, 3-amino-1-pentanol, Diol, 2-amino-1,3-propanediol, 4-amino-1,2-butanediol and the like; Developing improvers such as mono [2- (meth) acryloyloxyethyl succinate], mono [2- (meth) acryloyloxyethyl] phthalate, and? -Carboxylic polycaprolactone mono (meth) acrylate; Siloxane oligomers having a reactive functional group disclosed in JP-A-2008-242078, and the like.

The coloring composition of the present invention can be prepared by a suitable method. When the present coloring agent is a dye, for example, the method described in Japanese Patent Application Laid-Open No. 2008-58642, Japanese Patent Application Laid-Open No. 2010-132874 . ≪ / RTI > In the case of using both of the present colorant and a pigment as dyes as a colorant, the dye solution containing the present colorant is passed through a first filter as disclosed in JP-A-2010-132874, Mixing the obtained dye solution with a separately prepared pigment dispersion or the like, and passing the obtained coloring composition through a second filter. In addition, the dye containing the present coloring agent, the components (B) to (C), and other components to be used as required are dissolved in a solvent, the resulting solution is passed through a first filter, A method in which one solution is mixed with a separately prepared pigment dispersion, and the resulting colored composition is passed through a second filter may be adopted. After the dye solution containing the colorant is passed through the first filter, the dye solution which has passed through the first filter is mixed with the other components (B) to (C) A method in which the obtained solution is passed through a second filter, the solution having passed through the second filter is mixed with a separately prepared pigment dispersion, and the resulting colored composition is passed through a third filter.

Color filter and its manufacturing method

The color filter of the present invention comprises a colored layer formed using the coloring composition of the present invention.

As a method for manufacturing a color filter, first, the following method can be mentioned. First, a light-shielding layer (black matrix) is formed on the surface of the substrate so as to partition a portion for forming a pixel as needed. Subsequently, the liquid composition of the blue radiation sensitive composition of the present invention containing the present coloring agent, for example, is applied on the substrate, followed by prebaking to evaporate the solvent to form a coating film. Subsequently, this coating film is exposed through a photomask and then developed with an alkali developer to dissolve and remove the unexposed portion of the coating film. Thereafter, post-baking forms a pixel array in which blue pixel patterns are arranged in a predetermined arrangement.

Subsequently, each of the radiation-sensitive coloring compositions of green or red was used, and each of the radiation-sensitive coloring compositions was applied, prebaked, exposed, developed, and postbaked in the same manner as above to form a green pixel array and a red pixel array Are sequentially formed on the same substrate. Thereby, a color filter in which pixel arrays of three primary colors of red, green, and blue are arranged on a substrate is obtained. However, in the present invention, the order of forming the pixels of each color is not limited to the above. Further, in the first method of manufacturing a color filter, it is preferable that at least one of the red and blue pixel arrays is a colored layer formed using the coloring composition of the present invention.

The black matrix can be formed by forming a thin film of metal such as chromium, which is formed by sputtering or vapor deposition, into a desired pattern by using a photolithography method. By using a radiation-sensitive coloring composition in which a black coloring agent is dispersed, As shown in Fig. The coloring composition of the present invention can be suitably used for the formation of such a black matrix.

Examples of the substrate used for forming the color filter include glass, silicon, polycarbonate, polyester, aromatic polyamide, polyamideimide, and polyimide.

These substrates may be subjected to appropriate pretreatment such as chemical treatment with a silane coupling agent or the like, plasma treatment, ion plating, sputtering, vapor phase reaction, vacuum deposition or the like, if desired.

When the radiation sensitive coloring composition is applied to a substrate, a suitable coating method such as a spraying method, a roll coating method, a rotation coating method (spin coating method), a slit die coating method or a bar coating method can be adopted, , It is preferable to adopt a slit die coating method.

Prebaking is usually carried out in combination with reduced pressure drying and heat drying. The reduced-pressure drying is usually carried out until 50 to 200 Pa is reached. The conditions for heating and drying are usually about 70 to 110 DEG C for about 1 to 10 minutes.

The coating thickness is usually 0.6 to 8 占 퐉, preferably 1.2 to 5 占 퐉, as a film thickness after drying.

Examples of the light source used for forming the pixel and / or the black matrix include a lamp light source such as a xenon lamp, a halogen lamp, a tungsten lamp, a high pressure mercury lamp, an ultra high pressure mercury lamp, a metal halide lamp, a medium pressure mercury lamp, A laser light source such as an ion laser, a YAG laser, an XeCl excimer laser, and a nitrogen laser. Ultraviolet LED can also be used as an exposure light source. Preferably, the wavelength is in the range of 190 to 450 nm.

In general, the exposure dose of the radiation is preferably 10 to 10,000 J / m ² .

Examples of the alkali developer include sodium carbonate, sodium hydroxide, sodium hydrogencarbonate, potassium hydroxide, tetramethylammonium hydroxide, choline, 1,8-diazabicyclo- [5.4.0] Diazabicyclo- [4.3.0] -5-nonene and the like are preferable.

A water-soluble organic solvent such as methanol or ethanol, a surfactant, or the like may be added to the alkali developing solution in an appropriate amount. After the alkali development, it is usually washed with water.

As the developing treatment method, a shower developing method, a spray developing method, a dip (immersion) developing method, a puddle (liquid buildup) developing method, and the like can be applied. The developing conditions are preferably 5 to 300 seconds at room temperature.

The post-baking condition is usually about 120 to 280 DEG C for about 10 to 60 minutes. From the viewpoint of the heat resistance of the present colorant, the post baking temperature is preferably 240 DEG C or less, particularly preferably 230 DEG C or less.

The film thickness of the thus formed pixel is usually 0.5 to 5 占 퐉, preferably 1.0 to 3 占 퐉.

As a second method for manufacturing a color filter, there is adopted a method of obtaining pixels of respective colors by an inkjet method disclosed in Japanese Patent Laid-Open Nos. 7-318723 and 2000-310706 . In this method, first, a partition wall serving also as a light shielding function is formed on the surface of the substrate. Subsequently, the liquid composition of the blue thermosetting coloring composition of the present invention containing the present coloring agent, for example, is ejected in the partition wall by the ink jet apparatus, and then the solvent is evaporated by prebaking. Subsequently, this coating film is exposed, if necessary, and then post-baked to form a blue pixel pattern.

Subsequently, a green pixel pattern and a red pixel pattern are successively formed on the same substrate in the same manner as above using each of the green and red thermosetting coloring compositions. Thereby, the color filter by which the pixel pattern of three primary colors of red, green, and blue is arrange | positioned on a board | substrate is obtained. However, in the present invention, the order of forming the pixels of each color is not limited to the above. Also in the second method of manufacturing a color filter, it is preferable that at least one of the red and blue pixel arrays is a colored layer formed using the coloring composition of the present invention.

In addition, since the partition wall functions not only to shield the light, but also to prevent coloring compositions of the respective colors ejected into the compartment from being mixed, the film thickness is thicker than that of the black matrix used in the first method. Therefore, a partition is normally formed using a black radiation sensitive composition.

The substrate or radiation source used for forming the color filter, and the methods and conditions of prebaking and postbaking are the same as those of the first method described above. The film thickness of the pixel formed by the ink jet method is about the same as the height of the partition wall.

After forming a protective film on the pixel pattern obtained in this way as needed, a transparent conductive film is formed by sputtering. After a transparent conductive film is formed, a spacer may be further formed to form a color filter. The spacer is usually formed using a radiation sensitive composition, and may be a spacer (black spacer) having light shielding properties. In this case, a radiation-sensitive coloring composition in which a black coloring agent is dispersed is used, and the coloring composition of the present invention can be preferably used for forming such a black spacer.

The color filter of the present invention thus obtained is extremely useful for a color liquid crystal display element, a color image pickup tube element, a color sensor, an organic EL display element, and an electronic paper because of its extremely high luminance and color purity.

Display element

The display element of this invention is equipped with the color filter of this invention. As a display element, a color liquid crystal display element, an organic electroluminescent display element, an electronic paper, etc. are mentioned.

The color liquid crystal display device having the color filter of the present invention may be of a transmissive type or a reflective type, and may have a suitable structure. For example, a color filter may be formed on a substrate separate from a driving substrate on which a thin film transistor (TFT) is disposed, and a substrate on which a driving substrate and a color filter are formed may face the liquid crystal layer, The substrate on which the color filter is formed on the surface of the driving substrate on which the thin film transistor (TFT) is disposed and the substrate on which the ITO (indium-doped indium oxide) electrode are formed may be opposed to each other through the liquid crystal layer . The latter structure is advantageous in that the aperture ratio can be remarkably improved and a bright and precise liquid crystal display element can be obtained.

The color liquid crystal display device having the color filter of the present invention may have a backlight unit using a white LED as a light source in addition to a cold cathode fluorescent lamp (CCFL). Examples of white LEDs include white LEDs that combine red LEDs, green LEDs, and blue LEDs to obtain white light by mixing colors, white LEDs that combine blue LEDs with red LEDs and green phosphors to obtain white light by mixing colors, A white LED for obtaining a white light by mixing a light emitting fluorescent substance and a green light emitting phosphor and a white LED for obtaining a white light by mixing a blue LED and a YAG fluorescent substance, a blue LED, an orange light emitting phosphor and a green light emitting phosphor are combined and mixed A white LED for obtaining white light, an ultraviolet LED, a white LED for obtaining a white light by mixing a red light emitting phosphor, a green light emitting phosphor and a blue light emitting phosphor in combination, and the like.

The color liquid crystal display device having the color filter of the present invention may be applied to a color liquid crystal display device such as TN (Twisted Nematic) type, STN (Super Twisted Nematic) type, IPS (In-Planes Switching) type, VA (Vertical Alignment) type, OCB (Optically Compensated Birefringence) Type liquid crystal mode can be applied.

Further, the organic EL display device having the color filter of the present invention can adopt a suitable structure, for example, a structure disclosed in Japanese Patent Laid-Open No. 11-307242.

Further, the electronic paper having the color filter of the present invention can adopt a suitable structure, for example, a structure disclosed in Japanese Patent Application Laid-Open No. 2007-41169.

<Examples>

Hereinafter, an Example is given and embodiment of this invention is described further more concretely. However, the present invention is not limited to the following examples.

&Lt; Synthesis and evaluation of the present colorant &

1. Synthesis of the present colorant

Synthesis Example 1

(1.0 part by mass), 4- (N, N-dimethylamino) pyridine (1.4 parts by mass), 2-hydroxyethyl methacrylate (18 parts by mass), and the mixture was stirred for about 30 minutes. Thereafter, anhydrous chloroform (47 parts by mass) was added to 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (10.5 parts by mass) to slowly dissolve the solution, Lt; / RTI &gt; The separation operation was carried out twice with a 1N hydrochloric acid aqueous solution (150 parts by mass), and then the organic layer was washed twice with 10% brine (150 parts by mass). Subsequently, 43 parts by mass of anhydrous magnesium sulfate was added and stirred for about 30 minutes. The drying agent was filtered and the solvent was distilled off to obtain 20.6 parts (yield: 90%) of a compound represented by the following formula (A1). The resulting compound is referred to as a colorant (A-1).

Synthesis Example 2

(20 parts by weight) and bis (trifluoromethanesulfonyl) imide lithium (14.5 parts by weight) were placed in a 500 mL Erlenmeyer flask equipped with a stirrer, and chloroform (130 parts by weight) Mass part) was added, and the mixture was stirred at room temperature for about 2 hours. Thereafter, the water layer was separated and removed, and the organic layer was washed twice with ion exchange water (200 parts by mass). The organic layer was concentrated under reduced pressure, and the residue was dried under reduced pressure at 50 캜 for 12 hours to obtain 26.6 parts (yield: 94%) of a compound represented by the following formula (A2). ¹ H-NMR (solvent: deuterated chloroform) measurement confirmed the target compound. The resulting compound is referred to as a colorant (A-2).

Synthesis Example 3

A colorant was synthesized in the same manner as in Synthesis Example 2 except that potassium tetracyano borate was used in place of lithium bis (trifluoromethanesulfonyl) imide in Synthesis Example 2, and ¹ H-NMR (solvent: deuterated chloroform) The target compound was confirmed by measurement. The resulting compound is referred to as a colorant (A-3).

Synthesis Example 4

A colorant was synthesized in the same manner as in Synthesis Example 2 except that potassium trifluoromethanesulfonate was used in place of lithium bis (trifluoromethanesulfonyl) imide in Synthesis Example 2, and ¹ H-NMR (solvent: deuterated chloroform ) Was confirmed to be the target compound. The resulting compound is referred to as a colorant (A-4).

Synthesis Example 5

The procedure of Synthesis Example 2 was repeated except that 2-acryloyloxy-1,1,2,2-tetrafluoroethanesulfonic acid potassium was used instead of bis (trifluoromethanesulfonyl) imide lithium in Synthesis Example 2 A colorant was synthesized and it was confirmed to be the target compound by ¹ H-NMR (solvent: deuterated chloroform) measurement. The obtained compound is referred to as a colorant (A-5).

Synthesis Example 6

Except that in Synthesis Example 2, potassium 2- (4-vinylphenyloxy) -1,1,2,2-tetrafluoroethanesulfonate was used in place of lithium bis (trifluoromethanesulfonyl) imide in Synthesis Example 2 , A colorant was synthesized in the same manner as in Example ¹ , and it was confirmed to be the target compound by ¹ H-NMR (solvent: deuterated chloroform) measurement. The resulting compound is referred to as a colorant (A-6).

Synthesis Example 7

A colorant was synthesized in the same manner as in Synthesis Example 2 except that tris (trifluoromethylsulfonyl) methide cesium was used instead of bis (trifluoromethanesulfonyl) imide lithium in Synthesis Example 2, and ¹ H-NMR (Solvent: deuterated chloroform). The resulting compound is referred to as a colorant (A-7).

Synthesis Example 8

A colorant was synthesized in the same manner as in Synthesis Example 1 except that 2-hydroxyethyl acrylate was used in place of 2-hydroxyethyl methacrylate in Synthesis Example 1, and the colorant was analyzed by ¹ H-NMR (solvent: deuterated chloroform) Was confirmed to be the desired compound. Let the obtained compound be a coloring agent (A-8).

2. Evaluation of the present colorant

The colorants (A-1) to (A-8) obtained in Synthesis Examples 1 to 8 were dissolved in cyclohexanone in an amount of 10 mass% or more, and these solutions were blue.

The 5% mass reduction temperature based on simultaneous thermogravimetric and differential thermal analysis of the colorants (A-1) to (A-8) was 250 ° C or more. On the other hand, the 5% mass reduction temperature based on the simultaneous thermogravimetric and differential thermal analysis of C. I. Basic Violet 10 was less than 200 占 폚. It can also be said that the higher the 5% mass reduction temperature based on simultaneous thermogravimetric and differential thermal analysis, the higher the heat resistance of the colorant.

<Production of Dye Solution>

Production Example 1

20 parts by weight of the colorant (A-1) and 80 parts by weight of propylene glycol monomethyl ether as a solvent were mixed to prepare a dye solution (A-1).

Production Examples 2 to 8

(A-2) to (A-8) were obtained in the same manner as in Production Example 1 except that the colorants (A-2) to (A-8) were used instead of the colorant (A- .

Production Example 9

A dye solution (A-9) was prepared in the same manner as in Production Example 1 except that Basic Violet 10 was used instead of the colorant (A-1) in Production Example 1.

<Synthesis of Binder Resin>

Synthesis Example 9

In a flask equipped with a cooling tube and a stirrer, 100 parts by mass of propylene glycol monomethyl ether acetate was placed and replaced with nitrogen. And heated at 80 占 폚. At the same temperature, 100 parts by mass of propylene glycol monomethyl ether acetate, 20 parts by mass of methacrylic acid, 10 parts by mass of styrene, 5 parts by mass of benzyl methacrylate, 15 parts by mass of 2-hydroxyethyl methacrylate, 23 parts by mass of 2-ethylhexyl methacrylate, 12 parts by mass of N-phenylmaleimide, 15 parts by mass of succinic acid mono (2-acryloyloxyethyl) and 2,2'-azobis (2,4- Nitrile) was added dropwise over 1 hour, and the mixture was polymerized at this temperature for 2 hours. Thereafter, the temperature of the reaction solution was raised to 100 占 폚 and further polymerized for 1 hour to obtain a binder resin solution (solid content concentration: 33% by mass). Obtained binder resin had Mw of 12,200 and Mn of 6,500. This binder resin is referred to as "binder resin (B1)".

&Lt; Production of Pigment Dispersion >

Production Example 10

15 parts by mass of CI Pigment Red 254 as a coloring agent, 12.5 parts by mass (solid content concentration: 40% by mass) of BYK-LPN21116 (manufactured by BYK) as a dispersant and 72.5 parts by mass of propylene glycol monomethyl ether acetate as a solvent And treated with a beads mill to prepare a pigment dispersion (a-1).

&Lt; Preparation and evaluation of colored composition >

Example 1

13.5 parts by mass of the pigment dispersion (a-1), 7.2 parts by mass of the dye solution (A-1), 21.6 parts by mass of the binder resin (B1) solution as the binder resin, M- 9.2 parts by mass of a mixture of lithol hexaacrylate and dipentaerythritol pentaacrylate), 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one as a photopolymerization initiator , 2.2 parts by mass of a fluorine-based surfactant (trade name: IRGACURE 369, manufactured by Chemical Co., Ltd.) and NCI-930 (manufactured by Adeka Corp.)), 0.2 parts by mass of Megaface F- Propylene glycol monomethyl ether as a solvent was mixed to prepare a coloring composition (CR1) having a solid content concentration of 20 mass%.

The coloring composition (CR1) was coated on a glass substrate using a spin coater and then pre-baked on a hot plate at 80 DEG C for 10 minutes to form a coating film. The number of revolutions of the spin coater was changed and three coating films having different film thicknesses were formed by the same operation.

Subsequently, these substrates were cooled to room temperature, irradiated with radiation of each wavelength of 365 nm, 405 nm, and 436 nm at an exposure dose of 2,000 J / m ² on each coating film without using a photomask, using a high pressure mercury lamp Respectively. Subsequently, a developer consisting of 0.04 mass% aqueous potassium hydroxide solution at 23 캜 was ejected onto these substrates at a developing pressure of 1 kgf / cm ² (nozzle diameter: 1 mm) to perform showering for 90 seconds. Thereafter, the substrate was cleaned with ultra-pure water, air-dried, and post-baked in a clean oven at 230 캜 for 30 minutes to form a cured film for evaluation.

Evaluation of voltage holding ratio (%)

The obtained color composition was spin-coated on a soda glass substrate on which an SiO ₂ film was formed to prevent elution of sodium ions on the surface and an ITO (indium-tin oxide alloy) electrode was deposited in a predetermined shape, The plate was prebaked for 1 minute to form a film having a film thickness of 2.0 mu m. Subsequently, the film was exposed at an exposure amount of 700 J / m ² without passing through the photomask. Thereafter, this substrate was immersed in a developer composed of 0.04 mass% aqueous solution of potassium hydroxide at 23 캜 for 1 minute and developed, and then washed with ultrapure water, air-dried, post-baked at 230 캜 for 30 minutes, To form a permanent cured film. Subsequently, the substrate on which the pixel was formed and the substrate on which the ITO electrode was vapor-deposited in a predetermined shape were bonded to each other with a sealing material mixed with glass beads of 1.8 mm, and the liquid crystal cell (MLC6608) Respectively. Subsequently, the liquid crystal cell was placed in a thermostatic chamber at 60 ° C, and the voltage holding ratio of the liquid crystal cell was measured by a liquid crystal voltage maintaining rate measuring system (Model VHR-1A, manufactured by Toyo Technica Co., Ltd.). The applied voltage was a square wave of 5.5 V and a measurement frequency of 60 Hz. Here, the voltage holding ratio is a value obtained by (a voltage applied at a liquid crystal cell potential difference after 16.7 milliseconds / a voltage applied at 0 milliseconds). If the voltage holding ratio of the liquid crystal cell is 90% or less, the liquid crystal cell can not keep the applied voltage of 16.7 milliseconds at a predetermined level and can not orient the liquid crystal sufficiently, and there is a fear of causing "baking" .

Examples 2 to 8 and Comparative Example 1

A coloring composition was prepared in the same manner as in Example 1 except that the kind and amount of the pigment dispersion and dye solution in Example 1 were changed as shown in Table 1. Then, the obtained coloring composition was evaluated in the same manner as in Example 1. The evaluation results are shown in Table 1.

Claims (6)

(A) a xanthan-based colorant having a (meth) acryloyl group in a color developing moiety;
(B) a binder resin; And
(C) Crosslinking agent
, And the xanthene colorant has a structure represented by the following chemical formula (1).

[In the formula (1)
R ^a represents a group having ^a (meth) acryloyl group,
R ¹ to R ⁴ independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, or a phenyl group (said alkyl group, cycloalkyl group or phenyl group may have a substituent)
R ⁵ and R ⁶ independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a chlorine atom,
r represents an integer of 1 to 5, and when r is an integer of 2 or more, a plurality of R ^a may be the same or different; The coloring composition according to claim 1, wherein the xanthene colorant has a structure represented by the following formula (2).

[In the formula (2)
R ^b represents a group having a (meth) acryloyl group,
R ¹ to R ⁴ independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, or a phenyl group (said alkyl group, cycloalkyl group or phenyl group may have a substituent)
R ⁵ and R ⁶ independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a chlorine atom] The coloring composition according to claim 2, wherein the group R ^b is a group represented by the following formula (2a) or (2b).

[In formulas (2a) and (2b)
R ¹⁰ and R ¹¹ independently represent a hydrogen atom or a methyl group,
Y ¹ , Y ² , Y ³ and Y ⁴ independently represent a substituted or unsubstituted alkanediyl group having 1 to 12 carbon atoms,
Z represents a -CO- group or a -COO- (*) group (* represents a bond with Y ² )
Q represents a divalent alicyclic hydrocarbon group,
p ¹ represents an integer of 0 to 12,
p ² and p ³ independently represent an integer of 0 to 6; The coloring composition according to claim 1, wherein the xanthene colorant is obtained by an esterification reaction between a compound represented by the following formula (3) and a compound having a hydroxyl group and a (meth) acryloyl group.

[In the formula (3)
R ¹ to R ⁴ independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, or a phenyl group (said alkyl group, cycloalkyl group or phenyl group may have a substituent)
R ⁵ and R ⁶ independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a chlorine atom,
X ^- represents a halogen ion, a boron anion, a phosphate anion, a carboxylic acid anion, a sulfuric acid anion, an organic sulfonic acid anion, a nitrogen anion, or a methide anion. A color filter comprising a coloring layer formed using the coloring composition of any one of claims 1 to 4. A display device comprising the color filter of claim 5.