KR101980236B1 - Colored composition, color filter, display device and pigment dispersion - Google Patents

Abstract

[PROBLEMS] To provide a coloring composition suitable for forming a coloring layer capable of achieving both heat resistance and solvent resistance.
(B) a colorant composition containing (B) a colorant containing a lake pigment, (B) a dispersant and (C) a crosslinking agent, and (B) a repeating unit having an oxygen- (B-2) a urethane bond-containing dispersing agent and (B-3) a (meth) acrylic dispersing agent (excluding the component (B-1) By weight based on the total weight of the composition.

Description

COLOR COMPOSITION, COLOR FILTER, DISPLAY DEVICE AND PIGMENT DISPERSION BACKGROUND OF THE INVENTION 1. Field of the Invention [0001]

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 color filter, 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 color filter having a colored layer formed using the colored composition, and a display device having the color filter.

In the production of a color filter using a coloring and radiation-sensitive composition, a coloring and radiation-sensitive composition of a pigment dispersion type is coated on a substrate and dried, and then the dry film is irradiated with radiation in a desired pattern shape (Refer to, for example, Patent Documents 1 and 2) are known. A method of forming a black matrix using a photopolymerizable composition in which carbon black is dispersed (see, for example, Patent Document 3) is also known. There is also known a method of obtaining a pixel of each color by an ink jet method using a pigment dispersion type colored resin composition (see, for example, Patent Document 4).

In manufacturing a color filter, a high-temperature process exceeding 200 캜 is generally required, so that a color filter is required to have high heat resistance. Recently, color filters having excellent chromaticity characteristics are required. In order to simultaneously achieve these demands, studies have been made to apply a rake pigment to a coloring agent of a coloring composition for a color filter. For example, Patent Document 5 reports a color filter comprising a coloring layer formed of a coloring composition containing a rake pigment and a specific dispersing agent. Further, Patent Document 6 reports a color filter formed using a coloring composition comprising a lake pigment and a resin having an ethylenically unsaturated double bond in a side chain.

(Patent Document 1) JP-A-2-144502

(Patent Document 2) JP-A-3-53201

(Patent Document 3) JP-A-6-35188

(Patent Document 4) Japanese Patent Laid-Open Publication No. 2000-310706

(Patent Document 5) JP-A No. 2011-6602

(Patent Document 6) Japanese Laid-Open Patent Publication No. 2012-8421

However, according to the study of the present inventors, it has been found that the color filter comprising the colored layer formed using the coloring composition disclosed in Patent Documents 5 and 6 has poor balance of heat resistance and solvent resistance.

Accordingly, an object of the present invention is to provide a coloring composition which is suitable for forming a coloring layer capable of achieving both heat resistance and solvent resistance. It is another object of the present invention to provide a color filter comprising a colored layer formed using the above colored composition and a display element having the color filter.

In view of the above circumstances, the present inventors have conducted intensive studies and, as a result, have found that the above problems can be solved by using a colorant containing a lake pigment together with a specific dispersant.

That is, the present invention relates to a colored composition comprising (A) a colorant containing a lake pigment, (B) a dispersant and (C) a crosslinking agent, and (B) a repeating unit having a saturated oxygen- (B-2) a urethane bond-containing dispersing agent and (B-3) a (meth) acrylic dispersing agent (excluding the component (B-1) By weight of the coloring composition.

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

The present invention also provides a pigment dispersion containing (a1) a lake pigment, (B-1) a copolymer comprising a repeating unit having an oxygen-containing saturated heterocyclic group, and (F) a solvent.

By using the coloring composition of the present invention, it is possible to form a coloring layer having both high heat resistance and high solvent resistance. Therefore, the coloring composition of the present invention is suitable 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, Can be used.

(Mode for carrying out the invention)

Hereinafter, the present invention will be described in detail.

Coloring composition

Hereinafter, the constituent components of the coloring composition of the present invention will be described in detail.

- (A) Colorant -

The coloring composition of the present invention comprises (A) a rake pigment (a1) as a colorant. Examples of the precipitating agent include barium chloride, calcium chloride, ammonium sulfate, aluminum chloride, aluminum acetate, lead acetate, tannic acid, catanil, and tamarind , Isopoly acid, and heteropoly acid. Examples of the isopolyacids include isopoly-tungstic acid, isopolyvananadic acid, and isopolymolybdic acid. Examples of the heteropoly acid include phosphotungstic acid, phosphomolybdic acid, phospho Tungsten-molybdic acid, silico tungsten molybdic acid, silicotungstic acid, and silicomolybdic acid. Of these, isopiolic acid and heteropoly acid are preferable as the precipitant, heteropoly acids containing molybdenum atoms are more preferable, and phosphotungsten-molybdic acid is more preferable.

As such a rake pigment, there can be mentioned, for example, a color index (C.I.) name as shown below.

C.I. Pigment Yellow 61, C.I. Pigment Yellow 61: 1, C.I. Pigment Yellow 62, C.I. Pigment Yellow 100, C.I. Pigment Yellow 104, C.I. Pigment Yellow 133, C.I. Pigment Yellow 169, C.I. Pigment Yellow 183, C.I. Pigment Yellow 191, C.I. Pigment Yellow 191: 1, C.I. Pigment Yellow 206, C.I. Pigment Yellow 209, C.I. Pigment Yellow 209: 1, C.I. Pigment Yellow 212;

C.I. Pigment Red 48: 1, C.I. Pigment Red 48: 2, C.I. Pigment Red 48: 3, C.I. Pigment Red 48: 4, C.I. Pigment Red 48: 5, C.I. Pigment Red 49, C.I. Pigment Red 49: 1, C.I. Pigment Red 49: 2, C.I. Pigment Red 49: 3, C.I. Pigment Red 52: 1, C.I. Pigment Red 52: 2, C.I. Pigment Red 53: 1, C.I. Pigment Red 54, C.I. Pigment Red 57: 1, C.I. Pigment Red 58, C.I. Pigment Red 58: 1, C.I. Pigment Red 58: 2, C.I. Pigment Red 58: 3, C.I. Pigment Red 58: 4, C.I. Pigment Red 60: 1, C.I. Pigment Red 63, C.I. Pigment Red 63: 1, C.I. Pigment Red 63: 2, C.I. Pigment Red 63: 3, C.I. Pigment Red 64: 1, C.I. Pigment Red 68, C.I. Pigment Red 81, C.I. Pigment Red 81: 1, C.I. Pigment Red 200, C.I. Pigment Red 237, C.I. Pigment Red 239, C.I. Pigment Red 247;

C.I. Pigment Violet 2, C.I. Pigment Violet 3, C.I. Pigment Violet 3: 1, C.I. Pigment Violet 3: 3, C.I. Pigment Violet 27, C.I. Pigment Violet 39;

C.I. Pigment Blue 1, C.I. Pigment Blue 2, C.I. Pigment Blue 3, C.I. Pigment Blue 9, C.I. Pigment Blue 10, C.I. Pigment Blue 14, C.I. Pigment Blue 17: 1, C.I. Pigment Blue 24, C.I. Pigment Blue 24: 1, C.I. Pigment Blue 56, C.I. Pigment Blue 61, C.I. Pigment Blue 62;

C.I. Pigment Green 1, C.I. Pigment Green 4.

Among these lake pigments, at least one species selected from triarylmethane lake pigments and xanthate lake pigments is preferable, and in particular, C.I. Pigment Blue 1, C.I. Pigment Blue 2, C.I. Pigment Blue 3, C.I. Pigment Blue 9, C.I. Pigment Blue 10, C.I. Pigment Blue 14, C.I. Pigment Blue 61, C.I. Pigment Blue 62, C.I. Pigment Violet 1, C.I. Pigment Violet 2, C.I. Pigment Violet 3, C.I. Pigment Violet 27, C.I. Pigment Violet 39 and the like, and C.I. Pigment Red 81, C.I. Pigment Red 81: 1, C.I. Pigment Red 81: 2, C.I. Pigment Red 81: 3, C.I. Pigment Red 81: 4, C.I. Pigment Red 81: 5, C.I. Pigment Red 169, C.I. Pigment Violet 1, C.I. Pigment Violet 1: 1, C.I. Pigment Violet 1: 2, C.I. Pigments such as Pigment Violet 2 are preferred from the viewpoint of the chromaticity characteristics. It is also possible to use a triarylmethane lake pigment prepared by using isopoly acid or heteropoly acid as a precipitant, as disclosed in JP-A-2011-150195 and JP-A-2011-186043.

In the present invention, the lake pigment may be used singly or in a mixture of two or more kinds.

The coloring composition of the present invention may contain (A) as a coloring agent, (a1) a rake pigment and, in addition, other coloring agents. Other coloring agents are not particularly limited, and color and materials can be appropriately selected depending on the application.

As other coloring agents, any of pigments, dyes and natural pigments other than rake pigments can be used, but organic pigments and organic dyes other than rake pigments are preferred in the sense of obtaining pixels with high brightness and color purity.

Examples of the organic pigments other than the lake pigment include those classified as pigments in the color index (CI, published by The Society of Dyers and Colourists), that is, those having a color index (CI) name as described below .

C.I. Pigment Red 166, C.I. Pigment Red 177, C.I. Pigment Red 224, C.I. Pigment Red 242, C.I. Pigment Red 254, C.I. Red pigments such as Pigment Red 264;

C.I. Pigment Green 7, C.I. Pigment Green 36, C.I. Green pigments such as Pigment Green 58;

C.I. Pigment Blue 15: 6, C.I. Blue pigments such as Pigment Blue 80;

C.I. Pigment Yellow 83, C.I. Pigment Yellow 129, C.I. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment Yellow 150, C.I. Pigment Yellow 179, C.I. Pigment Yellow 180, C.I. Pigment Yellow 185, C.I. Pigment Yellow 211, C.I. Yellow pigments such as Pigment Yellow 215;

C.I. Pigment orange such as Pigment Orange 38;

C.I. Violet pigments such as Pigment Violet 23;

C.I. Pigment Black 1, C.I. Pigment Black 7 and other black pigments.

The coloring composition of the present invention is preferably used for forming a blue pixel or a red pixel when (A1) a triarylmethane-based rake pigment is used as a coloring agent. When the coloring composition of the present invention is used for forming a blue pixel, it is preferable that (A) the coloring agent (a1) is used together with the rake pigment in combination with at least one kind selected from the group consisting of a purple pigment and a blue pigment, Particularly, CI Pigment Blue 15: 6 and C.I. Pigment Violet < SEP > 23 < SEP > When the coloring composition of the present invention is used for forming a red pixel, it is preferable that (A) the coloring agent (a1) is used together with the rake pigment in combination with at least one kind selected from the group consisting of a red pigment and a purple pigment, , And in particular, CI Pigment Red 177 and C.I. Pigment Red 254, and the like.

In the present invention, when a pigment is used as the other colorant, the pigment may be purified and used by a recrystallization method, a reprecipitation method, a solvent cleaning method, a sublimation method, a vacuum heating method, or a combination thereof. The pigment may be used by modifying the surface of the particles with a resin, if desired. Examples of the resin for modifying the particle surface of the pigment include the vehicle resin described in JP 2001-108817 A, or a resin for dispersing various pigments commercially available. As the resin coating method for the surface of carbon black, for example, the methods described in JP-A-9-71733, JP-A-9-95625, JP-A-9-124969 and the like can be adopted . The organic pigment may be 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 Publication No. 8-179111 can be adopted.

In the present invention, when a pigment is used as the other coloring agent, a known dispersing aid may be further contained. Examples of known dispersing agents include pigment derivatives such as copper phthalocyanine, diketopyrrolopyrrole, and sulfonic acid derivatives of quinophthalone.

The dyes may be appropriately selected from among various kinds of oil soluble dyes, direct dyes, acid dyes and metal complex dyes, and examples thereof include those having the following color index (CI) names have.

C.I. Solvent Yellow 4, C.I. Solvent Yellow 14, C.I. Solvent Yellow 15, C.I. Solvent Yellow 24, C.I. Solvent Yellow 82, C.I. Solvent Yellow 88, C.I. Solvent Yellow 94, C.I. Solvent Yellow 98, C.I. Solvent Yellow 162, C.I. Solvent Yellow 179;

C.I. Solvent Red 45, C.I. Solvent Red 49;

C.I. Solvent Orange 2, C.I. Solvent Orange 7, C.I. Solvent Orange 11, C.I. Solvent Orange 15, C.I. Solvent Orange 26, C.I. Solvent Orange 56;

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

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

The content of the (A) coloring agent is usually from 5 to 70% by mass, preferably from 5 to 60% by mass in the solid content of the coloring composition in order to form a pixel having a high luminance and excellent color purity or a black matrix having excellent light- %to be. The solid content referred to herein is a component other than the solvent described later.

The proportion of (a1) the rake pigment is appropriately adjusted in accordance with the required degree of chromaticity. When the coloring composition of the present invention is used, (a1) the content of the rake pigment in the total coloring agent is 30% And even when it is 60 mass% or more, a colored layer excellent in heat resistance and solvent resistance can be formed.

- (B) Dispersant -

(B-1) copolymer containing a repeating unit having an oxygen-containing saturated heterocyclic group (hereinafter also referred to as "(B-1) copolymer") as the dispersing agent (B) as the dispersing agent (B) (B-2) a urethane bond-containing dispersing agent and (B-3) a (meth) acrylic dispersing agent (excluding the component (B-1)).

First, the (B-1) copolymer will be described. The copolymer (B-1) in the present invention has a repeating unit having an oxygen-containing saturated heterocyclic group (hereinafter also referred to as "repeating unit (3)") and functions as a dispersant for the colorant (A).

The "oxygen-containing saturated heterocyclic group" in the present invention means a saturated heterocyclic group having an oxygen atom as a heteroatom constituting a heterocyclic ring, and among them, a cyclic ether group having 3 to 7 atoms constituting the ring is preferable Specific examples thereof include an oxiranyl group such as a glycidyl group, a 2-methylglycidyl group and a glycidoxin group; Oxetanyl groups such as a 3-methyloxetan-3-yl group, a 3-ethyloxetan-3-yl group, a 3-methyloxetan-3-ylmethoxy group and a 3-ethyloxetan-3-ylmethoxy group; 3,4-epoxycyclohexyl group; Tetrahydrofuran-2-yl group, tetrahydrofuran-3-yl group, and other tetrahydrofuranyl groups; A tetrahydropyranyl group such as a tetrahydropyran-2-yl group, a tetrahydropyran-3-yl group and the like. Of these, an oxiranyl group, an oxetanyl group, a 3,4-epoxycyclohexyl group and a tetrahydrofuranyl group are preferable in that the desired effect is more remarkably obtained.

As the repeating unit (3), there may be mentioned, for example, a repeating unit represented by the following formula (3):

[In the formula (3)

R ⁸ represents a hydrogen atom or a methyl group,

Q represents an oxygen-containing saturated heterocyclic group,

X ² represents a single bond or a divalent linking group.

In the above formula (3), as R ⁸ , a methyl group is preferable among a hydrogen atom and a methyl group.

2 As the divalent linking group (X ^2), for ^{example, -CONH-R 9 - (*} 2) ^{group, -COO-R 10 - (*} 2) ^{group, -COO-R 11 -OOCNH-R} 12 - (* ² ) group, -C ₆ H ₄ CH ₂ - (* ² ) group, -C ₆ H ₄ CH ₂ OR ¹³ - (* ² ) group and the like. Here, R ⁹ and R ¹⁰ independently represent a single bond, an alkanediyl group having 1 to 10 carbon atoms which may have a hydroxyl group, or an alkanedioxyalkanediyl group having 2 to 10 carbon atoms, and R ¹¹ and R ¹² Independently represent an alkanediyl group having 1 to 10 carbon atoms, R ¹³ represents an alkanediyl group having 1 to 10 carbon atoms which may have a hydroxyl group, (* ² ) .

As the alkanediyl group for R ⁹ to R ¹² , an alkanediyl group having 1 to 6 carbon atoms is preferable, and as the alkanediyl group for R ¹³ , an alkanediyl group having 2 to 6 carbon atoms is preferable. Specific examples include methylene, ethylene, ethane-1,1-diyl, propane-1,1-diyl, propane-1,2-diyl, propane- A butane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,4-diyl group, a pentane-1,5-diyl group, A hexane-1,5-diyl group, and a hexane-1,6-diyne group. In the present specification, the term " alkanedioxyalkanediyl group " refers to a group in which two alkanediyl groups are bonded through an oxygen atom. The alkanedioxyalkanediyl group is preferably an alkanedioxyalkanediyl group having 2 to 6 carbon atoms, and examples thereof include an ethyleneoxyethylene group, an ethyleneoxypropylene group, a propyleneoxypropylene group, and an ethyleneoxybutylene group. have.

Among them, X ^{2 is preferably} -COO-R ¹⁰ - (* ² ) group or -COO-R ¹¹ -OOCNH-R ¹² - (* ² ) group.

(B-1) copolymer may have a repeating unit other than the above. Examples of such a repeating unit include repeating units represented by the following formula (1) (hereinafter also referred to as "repeating unit (1)") ); A repeating unit represented by the following formula (2) (hereinafter also referred to as "repeating unit (2)"); A repeating unit represented by the following formula (4) (hereinafter also referred to as "repeating unit (4)"); A repeating unit having an acidic group (hereinafter also referred to as "repeating unit (5)"); Styrene-based monomers such as styrene and? -Methylstyrene; (Meth) acrylic acid aralkyl esters such as benzyl (meth) acrylate; Quaternary ammonium salt structures such as (meth) acryloyloxyethyl (4-benzoylbenzyl) dimethylammonium bromide, (meth) acryloyloxyethylbenzyldimethylammonium chloride and (meth) acryloyloxyethylbenzyldiethylammonium chloride (Meth) acrylic acid ester; (Meth) acrylic acid halide monomers such as (meth) acrylic acid chloride; (Meth) acrylamide and N-methylol acrylamide; Vinyl acetate; Acrylonitrile; Allyl glycidyl ether; Allyl (meth) acrylate; 2- (2-vinyloxyethoxy) ethyl (meth) acrylate; Crotonic acid glycidyl ether; And repeating units derived from a monomer such as N-methacryloylmorpholine.

Among them, it is preferable to have a repeating unit (1) in terms of heat resistance and a repeating unit (2) in terms of dispersibility, and further, from the viewpoint of further improving the dispersibility, . Herein, in the present invention, "(meth) acrylate" means "acrylate or methacrylate"

[In the formula (1)

R ¹ represents a hydrogen atom or a methyl group,

Z represents -NR ² R ³ (wherein R ² and R ³ independently represent a hydrogen atom or a substituted or unsubstituted hydrocarbon group) or a substituted or unsubstituted nitrogen-containing heterocyclic group,

X ¹ represents a divalent linking group;

[In the formula (2)

R ⁴ represents a hydrogen atom or a methyl group,

R ⁵ represents an aliphatic hydrocarbon group or an alicyclic hydrocarbon group;

[In the formula (4)

R ¹⁴ represents a hydrogen atom or a methyl group,

R ¹⁵ independently represents an alkanediyl group having 2 to 4 carbon atoms,

R ¹⁶ represents an alkyl group having 1 to 6 carbon atoms,

n represents an integer of 1 to 150;

[In the formula (5)

R ¹⁷ represents a hydrogen atom or a methyl group,

A represents an acidic group,

And X ³ represents a single bond or a divalent linking group.

In the above formula (1), as R ¹ , a methyl group is preferable among a hydrogen atom and a methyl group.

In the above formula (1), Z represents -NR ² R ³ or a substituted or unsubstituted nitrogen-containing heterocyclic group, and R ² and R ³ independently represent a hydrogen atom or a substituted or unsubstituted hydrocarbon group. Here, in the present invention, the term "hydrocarbon group" is a concept including an aliphatic hydrocarbon group, an alicyclic hydrocarbon group and an aromatic hydrocarbon group, and may be any of linear, branched and cyclic. The aliphatic hydrocarbon group and the alicyclic hydrocarbon group may be either a saturated hydrocarbon group or an unsaturated hydrocarbon group, and the unsaturated bond may be present at an arbitrary position.

The aliphatic hydrocarbon group is preferably an aliphatic hydrocarbon group having 1 to 20 carbon atoms, more preferably an aliphatic hydrocarbon group having 1 to 12 carbon atoms. More specifically, examples thereof include an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, and an alkynyl group having 2 to 20 carbon atoms. The alkyl group is preferably an alkyl group having from 1 to 12 carbon atoms and specific examples thereof include a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, A heptyl group, a hexyl group, a heptyl group, an octyl group, a decyl group, and a dodecyl group. The alkenyl group is preferably an alkenyl group having from 2 to 12 carbon atoms. Specific examples thereof include an ethenyl group, a 1-propenyl group, a 1-butenyl group, a 1-butadienyl group, 1-hexenyl group, 2-ethyl-2-butenyl group, 2-octenyl group, (4-ethenyl) -5-hexenyl group and 2-decenyl group. As the alkynyl group, an alkynyl group having 2 to 12 carbon atoms is preferable, and specific examples thereof include an ethynyl group, 1-propynyl group, 1-butynyl group, 1-pentynyl group, 3-pentynyl group, 2-butynyl group, 2-octynyl group, (4-ethynyl) -5-hexynyl group and 2-decynyl group.

The alicyclic hydrocarbon group is preferably an alicyclic hydrocarbon group having 3 to 20 carbon atoms, and more preferably an alicyclic hydrocarbon group having 3 to 12 carbon atoms. Specific examples thereof include a cycloalkyl group having 3 to 20 carbon atoms. The cycloalkyl group is preferably a cycloalkyl group having from 3 to 12 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclodecyl group, And the like. Herein, in the present invention, the "alicyclic hydrocarbon group" is a generic name of a carbon-cyclic compound having a structure in which carbon atoms are bonded in a cyclic structure except for an aromatic compound, and the above-mentioned aliphatic hydrocarbon group has a substituent or a linking group with a nitrogen atom And the like.

The aromatic hydrocarbon group is preferably an aromatic hydrocarbon group having 6 to 20 carbon atoms, more preferably an aromatic hydrocarbon group having 6 to 14 carbon atoms. More specifically, an aryl group having 6 to 20 carbon atoms can be enumerated, and as the aryl group, an aryl group having 6 to 14 carbon atoms is preferable. Herein, in the present invention, the "aryl group" refers to a monocyclic to tricyclic aromatic hydrocarbon group, and specific examples thereof include a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, and an azulenyl group .

Examples of the substituent in the hydrocarbon group include a halogen atom, a hydroxyl group, and an alkoxy group having 1 to 6 carbon atoms. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an oxo atom. Specific examples of the alkoxy group having 1 to 6 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a pentyloxy group and a phenoxy group.

In the present invention, the "nitrogen-containing heterocyclic group" refers to a heterocyclic group having at least one nitrogen atom as a constituent of a ring, and is preferably a heterocyclic group or a condensed heterocyclic group formed by condensing two of them. These heterocyclic groups may be an unsaturated ring or a phar- maceutical ring, and may contain a hetero atom other than a nitrogen atom in the ring. Examples of the hetero atom other than the nitrogen atom include an oxygen atom and a sulfur atom.

Examples of the unsaturated heterocycle include a pyridine ring, an imidazole ring, a thiazole ring, an oxazole ring, a triazole ring, an imidazoline ring, and a piperazine ring. Examples of the saturated heterocycle include a morpholine ring, piperidine ring, and tetrahydropyrimidine ring.

The substituent in the nitrogen-containing heterocyclic group includes, for example, an alkyl group having 1 to 6 carbon atoms, a halogen atom, a carboxyl group, an ester group, an alkoxy group, a hydroxyl group, an amino group, an amide group, a thiol group, . Examples of the alkyl group having 1 to 6 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl and hexyl groups. . As the ester group, for example, an ester group having 1 to 7 carbon atoms is preferable, and specific examples include a methoxycarbonyl group, ethoxycarbonyl group, formyloxy group, acetoxy group, and benzoyloxy group. As the alkoxy group, an alkoxy group having 1 to 6 carbon atoms is preferable, and specific examples include the same ones as described above. Examples of the amino group include an amino group, a methylamino group, a diethylamino group and a diphenylamino group. Examples of the amide group include a formamide group, an acetamide group and a propioamide group . The thioether group is preferably a thioether group having 1 to 6 carbon atoms, and specific examples thereof include a methylthioether group, an ethylthioether group and a butylthioether group.

The above-mentioned heterocyclic group is preferably a 5- to 7-membered ring, and more specifically, a group having a basic skeleton represented by the following formula (1-1) may be mentioned, and these heterocyclic group may further have a substituent.

In Equation (1-1), " * " represents a combined hand.

Specific examples of the condensed heterocyclic group include groups having a basic skeleton represented by the following formulas (1-2) to (1-4), and these condensed heterocyclic groups may further have a substituent. Examples of the substituent include a halogen atom, a hydroxyl group, and an alkoxy group having 1 to 6 carbon atoms. Specific examples thereof include the same ones as described above.

In equations (1-2) to (1-4), " * "

In the formula (1), the divalent linking group (X ¹⁾ as, for example, in the alkanediyl group, an arylene group having a carbon number of 6~20, -CONH-R ⁶ having 1 to 10 carbon atoms (* ¹⁾ group, -COO-R ⁷ - (* ¹ ) group and the like. Here, R ⁶ and R ⁷ independently represent a single bond, an alkanediyl group having 1 to 10 carbon atoms, or an alkanedioxyalkanediyl group having 2 to 10 carbon atoms, (* ¹ ) Represents a combined hand.

The arylene group in X ¹ is preferably an arylene group having 6 to 14 carbon atoms, and the alkanediyl group in X ¹ , R ⁶ and R ⁷ is preferably an alkanediyl group having 1 to 6 carbon atoms, and R ^{As the} alkanediyloxyalkanediyl group in the formulas ( ⁶⁾ and ( ⁷⁾ , an alkanedioxyalkanediyl group having 2 to 6 carbon atoms is preferable. Specific examples thereof include the same ones as described above. Examples of the arylene group include a phenylene group, a naphthylene group, a biphenylene group, and an anthrylene group.

Among them, X ¹ is preferably -COO-R ⁷ - (* ¹ ) group, and R ⁷ is preferably an alkanediyl group having 2 to 6 carbon atoms.

In the formula (2), R ⁴ is preferably a methyl group in the hydrogen atom or the methyl group.

Examples of the aliphatic hydrocarbon group for R ⁵ include the same ones as described above.

Examples of the alicyclic hydrocarbon group for R ⁵ include a cycloalkyl group, a cycloalkenyl group, a condensed polycyclic hydrocarbon group, a crosslinked ring hydrocarbon group, a spiro hydrocarbon group, and a cyclic terpene hydrocarbon group. The alicyclic hydrocarbon group may have a substituent, and examples of the substituent include a halogen atom, a hydroxyl group, and an alkoxy group having 1 to 6 carbon atoms. Specific examples of these substituents include those described above.

Among them, R ⁵ is preferably an alkyl group having from 1 to 15 carbon atoms or an alicyclic hydrocarbon group having from 3 to 20 carbon atoms, more preferably an alkyl group having from 1 to 12 carbon atoms and an alicyclic hydrocarbon group having from 4 to 15 carbon atoms. Specific examples thereof include a methyl group, ethyl group, propyl group, butyl group, isobutyl group, t-butyl group, 2-ethylhexyl group, isodecyl group, dodecyl group, cyclohexyl group, 2-naphthyl group, tricyclo [5.2.1.0 ^2,6 ] decan-8-yl group, adamantyl group, dicyclopentenyl group, pentacyclopentadecanyl group, tricyclopentenyl group and isobornyl group.

In the formula (4), R ¹⁴ is preferably a hydrogen atom or a methyl group in the methyl group.

Examples of the alkanediyl group for R ¹⁵ include an ethylene group, an ethane-1,1-diyl group, a propane-1,1-diyl group, a propane-1,2-diyl group, A 3-diyl group, a propane-2,2-diyl group, a butane-1,2-diyl group, a butane-1,3-diyl group, and a butane-1,4-diyl group.

Examples of the alkyl group for R ¹⁶ include the same ones as described above.

n represents an integer of 1 to 150, preferably an integer of 1 to 20, more preferably an integer of 1 to 10, and particularly preferably an integer of 1 to 5.

The repeating unit (5) is gatjiman an acidic group, such as the acidic group is not particularly restricted but includes, for example, phenolic hydroxyl group, a carboxyl group, a sulfo _{group, -SO 2 NH 2, -C (} CF 3) 2 -OH , etc. . In the present invention, as the acidic group, a phenolic hydroxyl group and a carboxyl group are preferable, and a carboxyl group is particularly preferable in view of dispersibility and alkali developability of the resulting colored composition.

In the above formula (5), R ¹⁷ is preferably a methyl group in the hydrogen atom and the methyl group.

2 As the divalent linking group (X ^3), for example, alkanediyl group, an aryl group, -CONH-R ¹⁸ having a carbon number of 1 to 10 - (* ³⁾ group, -COO-R ¹⁹ - (* ³⁾ group, - OCOR ²⁰ - (* ^{3) group, -R 21 -OCO-R 22 -} (* 3) _{group, (C m H 2m COO)} -COO- l -C m H 2m - (* 3) group, -COO- R ²³ -OCO-R ²⁴ - (* ³ ) group and the like. Herein, R ¹⁸ to R ²² independently represent a single bond, an alkanediyl group having 1 to 10 carbon atoms, or an alkanedioxyalkanediyl group having 2 to 10 carbon atoms, m is an integer of 1 to 10 , 1 represents an integer of 1 to 4, R ²³ represents an alkanediyl group having 1 to 10 carbon atoms, R ²⁴ represents a single bond, an alkanediyl group having 1 to 10 carbon atoms, a cyclohexane-1,2- (* ³ ) represents a bonding hand which bonds with A.

The alkanediyl group in X ³ , R ¹⁸ to R ²² , R ²³ and R ²⁴ is preferably an alkanediyl group having 1 to 6 carbon atoms, and the arylene group in X ³ is preferably an arylene group having 6 to 14 carbon atoms Group is preferable, and as the alkanedioxyalkanediyl group in R ¹⁸ to R ²² , an alkanedioxyalkanediyl group having 2 to 6 carbon atoms is preferable. Specific examples of the alkanediyl group, arylene group and alkyleneoxyalkylene group include the same ones as described above. Specific examples of the phenylene group include, for example, 1,2-phenylene group and 1,4-phenylene group.

Examples In particular, ³ X, a single bond, phenylene ^{group, -COO-R 19 - (*} 3) _{group, (C m H 2m COO)} -COO- l -C m H 2m - (* 3) group or -COO -R ²³ -OCO-R ²⁴ - (* ³ ) group is preferable.

In the copolymer (B-1), the content ratio of each repeating unit is not particularly limited, but from the viewpoint of solvent resistance and heat resistance, the content of the repeating unit (3) By mass, more preferably 3 to 40% by mass, further preferably 5 to 30% by mass.

When the (B-1) copolymer further contains the repeating unit (1) and the repeating unit (2) in addition to the repeating unit (3), the content ratio of the repeating unit (1) It is preferably 5 to 60 mass%, more preferably 5 to 50 mass%, further preferably 10 to 40 mass%, particularly preferably 10 to 30 mass%, of the repeating units. The content of the repeating unit (2) is preferably 5 to 80% by mass, more preferably 10 to 75% by mass, further preferably 15 to 70% by mass in the total repeating units from the viewpoint of dispersibility.

When the (B-1) copolymer has the repeating unit (4) in addition to the repeating unit (1), the repeating unit (2) and the repeating unit (3) From the viewpoint of dispersibility, it is preferably 5 to 50% by mass, more preferably 10 to 40% by mass, further preferably 10 to 30% by mass in the total repeating units.

When the (B-1) copolymer has the repeating unit (5) in addition to the repeating unit (1), the repeating unit (2), the repeating unit (3) Is preferably 15 mass% or less, more preferably 10 mass% or less, further preferably 6 mass% or less, in the total repeating units, from the viewpoint of dispersibility. The lower limit of the content of the repeating unit (5) is not particularly limited, and may be 0 mass%, preferably 0.5 mass%, of the total repeating units.

The upper limit is preferably 250 mgKOH / g, more preferably 200 mgKOH / g, further preferably 150 mgKOH / g, particularly preferably 100 mgKOH / g, particularly preferably 60 mgKOH / g in view of heat resistance And the lower limit value is preferably 1 mg KOH / g, more preferably 10 mg KOH / g, further preferably 15 mg KOH / g. Herein, in the present invention, "amine value" means the number of mg of KOH equivalent to the acid required to neutralize 1 g of the non-volatile component excluding the solvent of the copolymer solution, specifically, the method described in Examples .

On the other hand, when the (B-1) copolymer has the repeating unit (5), the acid value of the (B-1) copolymer is preferably 30 mgKOH / g or less, Is not more than 25 mg KOH / g, more preferably not more than 20 mg KOH / g. The lower limit of the acid value is not particularly limited and may be 0 mgKOH / g, but is preferably 1 mgKOH / g. Here, in the present invention, the "acid value" means the number of mg of KOH required to neutralize 1 g of the non-volatile component excluding the solvent of the copolymer solution.

The repeating unit (3), the repeating unit (2), the repeating unit (4), and the repeating unit (3) are not particularly limited as long as they have the repeating unit (3) (2), a repeating unit (2), and a repeating unit (3), which have no repeating unit (1) 4) and the repeating unit (5). The AB block copolymer and the BAB block copolymer preferably contain a B block having at least one kind selected from the repeating units (1) to (4) and the repeating unit (5)

In the A block, the repeating unit (1) may contain two or more kinds of repeating units (A) in one A block. In such a case, each repeating unit may be any one of random copolymerization and block copolymerization ).

The repeating unit other than the repeating unit (1) may be contained in the A block. Examples of such repeating units include repeating units derived from the (meth) acrylic acid ester having the above quaternary ammonium salt structure.

On the other hand, in the B block, each repeating unit may be contained in any one of random copolymerization and block copolymerization, or two or more kinds thereof may be contained. When the (B-1) copolymer is a BAB block copolymer, the knitting of the repeating units constituting the two B blocks is not particularly limited, and examples thereof include repeating units (3), repeating units (2) (B1) having a repeating unit (3) and a B2 block having no repeating unit (2) and a repeating unit (4) -B2 block copolymer.

The weight average molecular weight (Mw) of the (B-1) copolymer in terms of polystyrene measured by gel permeation chromatography (hereinafter abbreviated as GPC) (elution solvent: dimethylformamide) is preferably 1,000 to 100,000, More preferably from 3,000 to 50,000, and still more preferably from 5,000 to 30,000. By such a configuration, the heat resistance and the solvent resistance can be compatible at a high level.

The ratio (Mw / Mn) of the weight average molecular weight (Mw) to the number average molecular weight (Mn) of the copolymer (B-1) in the present invention is preferably 1.0 to 5.0, 1.0 to 3.0. Here, Mn means the number average molecular weight in terms of polystyrene measured by GPC (elution solvent: dimethylformamide).

The copolymer (B-1) can be produced by a known method, but when the copolymer (B-1) is a block copolymer, for example, can do. Examples of the living polymerization method include those disclosed in JP-A-9-62002; Japanese Patent Application Laid-Open No. 2002-31713; P. Lutz, P. Masson et al., Polym. Bull. 12, 79 (1984); B. C. Anderson, G. D. Andrews et al., Macromolecules, 14, 1601 (1981); K. Hatada, K. Ute, et al., Polym. J. 17,977 (1985); K. Hatada, K. Ute, et al., Polym. J. 18, 1037 (1986); Ute Koichi, Koichi Hatada, Polymer Processing, 36, 366 (1987); Toshinobu Higashimura, Mitsuo Sawamoto, Polymer Journal, 46, 189 (1989); M. Kuroki, T. Aida, J. Am. Chem. Soc., 109, 4737 (1987); Takada Aida, Shohei Inoue, Organic Synthesis Chemistry, 43, 300 (1985); D. Y.Sogoh, W. R. Hertler et al., Macromolecules, 20, 1473 (1987); J. Polym.Sci.PaRta Polym. Chem., 47, 3773-3794 (2009); , J. Polym. Sci. Technol. Polym. Chem., 47, 3544-3557 (2009), and the like.

Examples of the monomer giving the repeating unit (3) include glycidyl (meth) acrylate, 2-methylglycidyl (meth) acrylate, 4-glycidyloxybutyl (meth) 3-ethyloxetane, 3 - [(meth) acryloyloxymethyl] oxetane, 3-vinylcyclohexylmethyl (meth) acrylate, Tetrahydrofurfuryl (meth) acrylate, 3 - [(meth) acryloyloxymethyl] -3-ethyloxetane, tetrahydrofurfuryl ) Ethyl (meth) acrylate. These may be used alone or in combination of two or more.

Examples of the monomer giving the repeating unit (1) include dimethylaminoethyl (meth) acrylate, dimethylaminopropyl (meth) acrylate, dimethylaminobutyl (meth) acrylate, diethylaminoethyl Acrylate, diethylaminobutyl (meth) acrylate, dimethylaminoethoxyethyl (meth) acrylate, dimethylaminoethoxypropyl (meth) acrylate, diethylaminobutoxybutyl (Meth) acrylate, and the like. These may be used alone or in combination of two or more.

Examples of the monomer giving the repeating unit (2) include monomers such as methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) (Meth) acrylate, dodecyl (meth) acrylate, cyclohexyl (meth) acrylate, isobutyl (meth) acrylate, t- acrylate, tricyclo [5.2.1.0 ^2,6] decane-8-yl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, dicyclopentenyl (meth) acrylate , Decahydro-2-naphthyl (meth) acrylate, pentacyclopentadecanyl (meth) acrylate, and tricyclopentenyl (meth) acrylate. These may be used alone or in combination of two or more.

Examples of the monomer to which the repeating unit (4) is given include monomers such as 2-methoxyethyl (meth) acrylate, methoxyethylene glycol (meth) acrylate, methoxy triethylene glycol (meth) (Meth) acrylate, methoxypropylene glycol (meth) acrylate, and methoxydipropylene glycol (meth) acrylate. As the monomer giving the repeating unit (4), PME-100, PME-200 (manufactured by Nichiyu Co., Ltd.) or the like may be used. These may be used alone or in combination of two or more.

Examples of the monomer giving the repeating unit (5) having an acidic group include (meth) acrylic acid, maleic acid, maleic anhydride, itaconic acid, Carboxypolycaprolactone mono (meth) acrylate, p-vinylbenzoic acid, p-hydroxystyrene, p-hydroxy (meth) acrylate, 2-carboxyethyl acrylate, mono [2- (meth) acryloyloxyethyl] acryloyloxyethylsulfonic acid, 2-acryloyloxyethylsulfonic acid, sodium 2-acryloyloxyethylsulfonate, lithium 2-acryloyloxyethylsulfonate, 2-acryloyloxyethyl Acryloyloxyethylsulfonic acid imidazolium, 2-acryloyloxyethylsulfonylpyridinium, 2-methacryloxyethylsulfonic acid sodium, 2-methacryloxyethylsulfonic acid lithium, 2-methacryloxyethyl Ammonium sulfonate, 2-methacryloxyethylsulfonic acid Imidazolium, 2-methacryloxyethylsulfonylpyridinium, styrenesulfonic acid, sodium styrenesulfonate, lithium styrenesulfonate, ammonium styrenesulfonate, styrenesulfonic acid imidazolium, and styrenesulfonic acid pyridinium. These may be used alone or in combination of two or more.

In the present invention, the content of the (B-1) copolymer is preferably 5 to 300 parts by mass, particularly preferably 10 to 200 parts by mass, per 100 parts by mass of the colorant (A). By such a structure, heat resistance and solvent resistance are both easily achieved.

In the present invention, (B-2) a dispersant having a urethane bond (hereinafter also referred to as a " urethane dispersant ") refers to a compound having at least one urethane bond in its structure.

In the present invention, the urethane bond of the urethane-based dispersant is preferably generated by reacting an aromatic polyisocyanate and / or an alicyclic polyisocyanate with a (poly) alcohol. Specific examples thereof include dispersants described in JP-A-2-19844 and JP-A-2007-269873. When two or more urethane bonds are present in the urethane-based dispersant, the respective urethane bonds may be the same or different.

Urethane-based dispersants are commercially available, for example,

EFKA-4046 (non-volatile component = 39 to 41 mass%, amine value: 17 to 21 mg KOH / g)

EFKA-4047 (nonvolatile component = 34 to 36 mass%, amine value: 14 to 20 mg KOH / g) [manufactured by EFKA Co.,

Disperbyk-161 (nonvolatile component = 30 mass%, amine value 11 mgKOH / g),

Disperbyk-162 (nonvolatile component = 38% by mass, amine value 13 mgKOH / g)

Disperbyk-163 (nonvolatile component = 45 mass%, amine value 10 mgKOH / g),

Disperbyk-164 (nonvolatile component = 60 mass%, amine value 18 mgKOH / g),

Disperbyk-166 (nonvolatile component = 30 mass%, amine value 20 mgKOH / g),

Disperbyk-167 (nonvolatile component = 52 mass%, amine value 13 mgKOH / g),

Disperbyk-168 (nonvolatile component = 30 mass%, amine value 11 mgKOH / g),

Disperbyk-182 (nonvolatile component = 43 mass%, amine value 13 mgKOH / g),

Disperbyk-2164 (nonvolatile component = 60% by mass, amine value: 14 mgKOH / g) [manufactured by BYK Corporation]

DISPARLON (manufactured by Kusumoto Kasei Co., Ltd.), etc., other than Solsperse 76500 (nonvolatile component = 50 mass%, amine value 15 mgKOH / g) It is possible. Herein, " amine value " means the number of mg of KOH required to neutralize 1 g of the solid content of the dispersant and the equivalent.

Among these urethane dispersants, those having an amine value of 80 mgKOH / g or less, preferably 50 mgKOH / g or less, and more preferably 30 mgKOH / g or less are preferred. The lower limit of the amine value may be 0 mgKOH / g, but is preferably 5 mgKOH / g, more preferably 10 mgKOH / g.

The urethane dispersant in the present invention has a weight average molecular weight (Mw) in terms of polystyrene measured by GPC of usually 5,000 to 50,000, preferably 7,000 to 20,000.

In the present invention, the urethane-based dispersing agents may be used alone or in combination of two or more.

The content of the urethane dispersant is usually 0.5 to 100 parts by mass, preferably 1 to 70 parts by mass, more preferably 10 to 50 parts by mass, and particularly preferably 35 to 50 parts by mass, relative to 100 parts by mass of the lake pigment in the colorant desirable. In this case, when the content of the urethane-based dispersant is less than 0.5 parts by mass, the stability and heat resistance of the pigment dispersion tend to be lowered. On the other hand, when the content is more than 100 parts by mass, the performance such as developability as a coloring resist may be impaired.

In the present invention, the term "(B-3) (meth) acrylic dispersant" (hereinafter also referred to as "(meth) acrylic dispersant") means a compound comprising a (co) polymer of a (meth) -1) component is excluded). The term "(meth) acrylic monomer" refers to a polymerizable compound having a (meth) acryloyl group in the molecule, and the term "(meth) acryloyl group" means an acryloyl group or a methacryloyl group .

In the present invention, as the (meth) acrylic dispersant, a block copolymer having a block obtained by polymerizing a (meth) acrylic monomer having a pigment adsorber and a block obtained by polymerizing a (meth) acrylic monomer having no pigment adsorber is preferable. Examples of the pigment adsorber include a carboxymethyl group, a sulfo group, a phosphonooxy group, an (N-substituted) amino group, an (N-substituted) ammonia group, (N-substituted) amino group, and (N-substituted) ammonia group are more preferable. Specifically, block copolymers described in JP-A-2002-31713, JP-A-2009-25813, and JP-A-2010-134419 can be mentioned.

Such dispersants are commercially available, for example,

Disperbyk-2000 (nonvolatile component = 40 mass%, amine value 4 mgKOH / g),

Disperbyk-2001 (nonvolatile component = 46 mass%, amine value 29 mgKOH / g),

BYK-LPN6919 (nonvolatile component = 60% by mass, amine value: 72 mgKOH / g)

BYK-LPN21116 (non-volatile component = 40 mass%, amine value 29 mg KOH / g)

BYK-LPN21324 (amine value 0 mgKOH / g) [manufactured by BYK Corporation] or the like.

Among the above (meth) acrylic dispersants, the amine value is preferably 130 mgKOH / g or less, more preferably 100 mgKOH / g or less, further preferably 80 mgKOH / g or less. The lower limit of the amine value may be 0 mgKOH / g, but is preferably 1 mgKOH / g, more preferably 3 mgKOH / g.

In the present invention, the (meth) acrylic dispersant may be used alone or as a mixture of two or more thereof.

The content of the (meth) acrylic dispersant is usually 0.5 to 100 parts by mass, preferably 1 to 70 parts by mass, and more preferably 1 to 50 parts by mass with respect to 100 parts by mass of the lake pigment in the colorant. In this case, when the content of the (meth) acrylic dispersant is less than 0.5 parts by mass, the stability and solvent resistance of the pigment dispersion tends to be lowered. On the other hand, when the content is more than 100 parts by mass, There is a concern.

The mass ratio [(B-2) / (B-3)] of the dispersant having the urethane bond (B-2) and the dispersant having the urethane bond (B-3) is preferably 5/95 to 95/5 , More preferably 10/90 to 90/10, and still more preferably 70/30 to 90/10. When the ratio of the urethane bond-containing dispersant to the (meth) acrylic-based dispersant is less than 5/95, the heat resistance tends to decrease. When the ratio of the urethane bond-containing dispersant to the (meth) acrylic-based dispersant exceeds 95/5, the solvent resistance tends to decrease.

In the present invention, in addition to the above (B-1) to (B-3), a known dispersant may be further contained. Examples of the known dispersant include a polyethyleneimine-based dispersant, a polyoxyethylene alkyl ether-based dispersant, a polyoxyethylene alkylphenyl ether-based dispersant, a polyethylene glycol diester-based dispersant, a sorbitan fatty acid ester-based dispersant, a polyester- .

Such a dispersant is commercially available, for example, as a polyethyleneimine-based dispersant, such as Solsulfur 24000 (manufactured by Lubrizol Corporation), as a polyester dispersant, and AJISPER-PB821, Agisper-PB822, Agisper-PB880, Agisper-PB881 (manufactured by Ajinomoto Fine Techno Co., Ltd.), and the like.

- (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 , A polyfunctional urethane (meth) acrylate obtained by reacting a (meth) acrylate having a hydroxyl group with a polyfunctional isocyanate, a (meth) acrylate having a hydroxyl group and an acid anhydride (Meth) acrylate having a carboxyl group obtained by reacting a polyfunctional (meth) acrylate.

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-valent 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 (meth) acrylate, 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, and hexahydrophthalic anhydride, anhydrous pyromellitic acid, biphenyltetracarboxylic acid 2 An anhydride, and a tetrabasic acid dianhydride such as benzophenone tetracarboxylic acid dianhydride.

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 bisphenol A di (meth) acrylate modified with at least one member selected from ethylene oxide and propylene oxide, at least one member selected from ethylene oxide and propylene oxide Trimethylolpropane tri (meth) acrylate modified with at least one member selected from isocyanuric acid tri (meth) acrylate, ethylene oxide and propylene oxide modified by at least one member selected from ethylene oxide and propylene oxide, (Meth) acrylate modified with at least one member selected from pentaerythritol tri (meth) acrylate, ethylene oxide and propylene oxide modified by a species, at least one member selected from the group consisting of pentaerythritol tetra Varied by species A dipentaerythritol penta (meth) acrylate, ethylene oxide and propylene oxide modified by at least one or dipentaerythritol hexa (meth) acrylate is selected from and the like.

Examples of the compound having two or more N-alkoxymethylamino groups include compounds having a melamine structure, a benzoguanamine structure, and a urea structure. The melamine structure and the benzoguanamine structure refer to a chemical structure 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) N, N ', N'-tetra (alkoxymethyl) glycoluril, and the like.

Among these crosslinking agents, polyfunctional (meth) acrylates, caprolactone modified polyfunctional (meth) acrylates, polyfunctional urethane (meth) acrylates obtained by reacting a trivalent or higher aliphatic polyhydroxy compound with (meth) acrylic acid, (Meth) acrylate having a carboxyl group, N, N, N ', N', N ", N" Guanamine is preferred. Among the polyfunctional (meth) acrylates obtained by reacting tri- or higher aliphatic polyhydroxy compounds with (meth) acrylic acid, trimethylolpropane triacrylate, pentaerythritol triacrylate, dipentaerythritol pentaacrylate, di Among the polyfunctional (meth) acrylates having a carboxyl group, pentaerythritol hexaacrylate is preferably a compound obtained by reacting pentaerythritol triacrylate with succinic anhydride, a compound obtained by reacting dipentaerythritol pentaacrylate with succinic anhydride Compound is particularly preferable in that the strength of the colored layer is high and the surface smoothness of the colored layer is excellent and plane contamination and film residue do not easily occur 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 in combination of two or more.

The content of the crosslinking agent (C) in the present invention is preferably from 10 to 1,000 parts by mass, particularly 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, the curability may be insufficient. On the other hand, when the content of the cross-linking agent is too large, when the alkali developability is imparted to the coloring composition of the present invention, the alkaline developability is lowered and flat contamination, film residue or the like easily occurs on the substrate of the unexposed portion or on the light- There is a tendency to lose.

- (D) Binder Resin -

The coloring composition of the present invention may contain (D) a binder resin (excluding the above component (B)). This makes it possible to improve the alkali developing property and the binding property to the substrate to the coloring composition. The binder resin (D) 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, and for example, an ethylenically unsaturated monomer having at least one carboxyl group (hereinafter also referred to as " unsaturated monomer (d1) And another copolymerizable ethylenically unsaturated monomer (hereinafter also referred to as " unsaturated monomer (d2) ").

Examples of the unsaturated monomer (d1) include unsaturated monomers such as (meth) acrylic acid, maleic acid, maleic anhydride, mono [2- (meth) acryloyloxyethyl], succinic acid monocaprolactone mono P-vinylbenzoic acid, and the like.

These unsaturated monomers (d1) may be used alone or in combination of two or more.

As the unsaturated monomer (d2), for example,

Substituted maleimides 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- (Meth) acrylate, polyethylene glycol (polymerization degree: 2 to 10), methyl ether (meth) acrylate, polypropylene glycol (polymerization degree: 2 to 10) , Polypropylene glycol (polymerization degree 2 to 10) mono (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decan- (Meth) acrylate, dicyclopentenyl (meth) acrylate, glycerol mono (meth) acrylate, 4-hydroxyphenyl (meth) acrylate, ethylene oxide- (Meth) acrylate, 3,4-epoxide Cyclohexylmethyl (meth) acrylate, 3 - [(meth) acryloyl-yloxymethyl] oxetane, 3- (meth) acrylic acid ester such as ethyl-3-oxetane [(meth) acryloyl-yloxymethyl];

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 macromonomers 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 (d2) may be used singly or in combination of two or more.

In the copolymer of the unsaturated monomer (d1) and the unsaturated monomer (d2), the copolymerization ratio of the unsaturated monomer (d1) in the copolymer is preferably 5 to 50 mass%, more preferably 10 to 40 mass% . By copolymerizing the unsaturated monomer (d1) in such a range, a colored composition excellent in alkali developability and storage stability can be obtained.

As specific examples of the copolymer of the unsaturated monomer (d1) and the unsaturated monomer (d2), for example, JP-A-7-140654, JP-A-8-259876, JP-A-10-31308 Japanese Laid-Open Patent Publication No. 10-300922, Japanese Laid-Open Patent Publication No. 11-174224, Japanese Laid-Open Patent Publication No. 11-258415, Japanese Laid-Open Patent Publication No. 2000-56118, Japanese Laid-Open Patent Publication No. 2004-101728, etc. And the like.

Further, in the present invention, for example, Japanese Unexamined Patent Application Publication No. 5-19467, Japanese Unexamined Patent Publication No. 6-230212, Japanese Unexamined Patent Publication No. 7-207211, Japanese Unexamined Patent Publication No. 09-325494 , JP-A-11-140144, and JP-A-2008-181095, it is also possible to use a method in which a carboxyl group-containing polymer having a polymerizable unsaturated bond, such as a (meth) acryloyl group, ) Binder resin.

The binder resin (D) in the present invention has a weight average molecular weight (Mw) in terms of polystyrene measured by GPC (dissolution solvent: tetrahydrofuran), usually 1,000 to 100,000, and preferably 3,000 to 50,000. If the Mw is too small, the residual film ratio of the resulting film may decrease, pattern shape, heat resistance, and the like may deteriorate and electrical characteristics may deteriorate. On the other hand, if Mw is too large, There is a fear that dry foreign matter tends to be generated at the time of applying by the slit nozzle method.

The ratio (Mw / Mn) of the weight average molecular weight (Mw) of the binder resin (D) to the number average molecular weight (Mn) in the present invention is preferably 1.0 to 5.0, 3.0. Herein, Mn means the number average molecular weight in terms of polystyrene measured by GPC (dissolution solvent: tetrahydrofuran).

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

In the present invention, the binder resin (D) may be used alone or in combination of two or more.

In the present invention, the content of the binder resin (D) is usually 10 to 1,000 parts by mass, preferably 20 to 500 parts by mass, per 100 parts by mass of the colorant (A). If the content of the binder resin is too small, for example, the alkali 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 colorant concentration is relatively decreased. May be difficult to achieve.

- (E) Photopolymerization initiator -

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

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

In the present invention, the photopolymerization initiator (E) may be used singly or in combination of two or more. As the photopolymerization initiator (E), at least one member selected from the group consisting of a thioxanthone compound, an acetophenone compound, a nonimidazole compound, a triazine compound, and an O-acyloxime compound is preferable.

Among the preferred photopolymerization initiators in the present invention, specific examples of the thioxanthone compounds include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2-isopropylthioxanthone, Ton, 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- (4-morpholinophenyl) butan-1-one and 2- (4-methylbenzyl) -2- (dimethylamino) -1- (4-morpholinophenyl) butan-1-one.

Specific examples of the imidazole-based 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 and the like.

When a non-imidazole-based compound is used as the photopolymerization initiator (E), it is preferable to use a hydrogen donor in combination with the fact that the sensitivity can be improved. The term "hydrogen donor" as used herein 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 mercapane-based hydrogen donors 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, but it is preferable to use one or more kinds of mercaptan-based hydrogen donors and one or more amine-based hydrogen donors in combination to further improve the sensitivity It is preferable.

Specific examples of the triazine-based compound include 2,4,6-tris (trichloromethyl) -s-triazine, 2-methyl-4,6-bis (trichloromethyl) (Trichloromethyl) -s-triazine, 2- [2- (furan-2-yl) ethenyl] -4 (Trichloromethyl) -s-triazine, 2- [2- (4-diethylamino-2-methylphenyl) ethenyl] -4,6-bis (Trichloromethyl) -s-triazine, 2- (4-methoxyphenyl) ethenyl] -4,6-bis (Trichloromethyl) -s-triazine, 2- (4-n-butoxyphenyl) - And triazine-based compounds having a halomethyl group such as 4,6-bis (trichloromethyl) -s-triazine.

Specific examples of the O-acyloxime compound include 1,2-octanedione, 1- [4- (phenylthio) phenyl] -, 2- (O-benzoyloxime), ethanone, 1- [ Yl] -, 1- (O-acetyloxime), ethanone, 1- [9-ethyl-6- -9H-carbazol-3-yl] -, 1- (O-acetyloxime), ethanone, 1- [ -Dimethyl-1,3-dioxoranyl) methoxybenzoyl} -9H-carbazol-3-yl] -, 1- (O-acetyloxime). As commercial products of O-acyloxime compounds, NCI-831 and NCI-930 (manufactured by ADEKA Corporation) 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, Ethyl 4-dimethylaminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoate, 2,5-bis (4-diethylaminobenzal) cyclohexanone, 7-diethylamino- 3- Benzoyl) coumarin, and 4- (diethylamino) chalcone. Further, in the present invention, the sensitivity of the coloring composition can be increased by containing the polyfunctional thiol which functions as a chain transfer agent. Examples of such a chain transfer agent include trimethylolpropane tris (3-mercaptopropionate), pentaerythritol tetrakis (3-mercaptopropionate), 2,4,6-trimercapto-s- Triazine, 2- (N, N-dibutylamino) -4,6-dimercapto-s-triazine and the like.

In the present invention, the content of the (E) 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 (E) photopolymerization initiator is too small, the curing by exposure may be insufficient, while if it is excessively large, the formed colored layer tends to be easily removed from the substrate at the time of development.

- (F) Solvent-

When the coloring composition of the present invention contains the above components (A) to (D) and optionally other components, it is usually formulated as a liquid composition by blending a solvent (F).

When the coloring composition of the present invention contains the above-mentioned components (A) to (C) and optionally other components, usually (A1) a colorant containing a lake pigment is dissolved in (F) (B) a dispersing agent, (D) a binder resin, for example, a bead mill, a roll mill or the like and pulverizing and mixing and dispersing the pigment dispersion to prepare a pigment dispersion, (D) a binder resin, (E) a photopolymerization initiator, and (F) a further solvent, if necessary, and then mixing them.

The solvent may be appropriately selected and used as long as the components constituting the coloring composition are dispersed or dissolved, and they do not react with these components and have volatility at an equilibrium.

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;

Alkoxycarbonic acids such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl ethoxyacetate and 3-methyl- Esters;

Amyl acetate, n-butyl acetate, ethyl butyrate, n-propyl butyrate, i-propyl butyrate, propyl acetate, isopropyl acetate, n- , 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 and N-methylpyrrolidone.

Among these solvents, those containing at least one selected from (poly) alkylene glycol monoalkyl ethers and (poly) alkylene glycol monoalkyl ether acetates are preferable from the viewpoints of solubility, pigment dispersibility, And at least one selected from propylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate and propylene glycol monoethyl ether acetate.

In the present invention, the (F) solvent may be used alone or in combination of two or more.

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

-additive-

The coloring composition of the present invention may contain various additives, if necessary.

As the additive, for example, a thermal polymerization initiator such as an azo-based compound or an organic peroxide; 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? -Carboxypolycaprolactone mono (meth) acrylate; Siloxane oligomers having reactive functional groups disclosed in JP-A-2008-242078, and the like.

Color filter and manufacturing method thereof

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

As a method of 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 such that a portion for forming a pixel is divided as necessary. Subsequently, a liquid composition of the radiation-sensitive coloring composition of the present invention, for example, in which a blue lake pigment is dispersed, is applied onto the substrate, and then the substrate is prebaked 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, by post-baking, a pixel array in which blue pixel patterns are arranged in a predetermined arrangement is formed.

Subsequently, each of the radiation-sensitive coloring compositions of green or red was used to apply, pre-baking, expose, develop and post-baking each of the radiation-sensitive coloring compositions in the same manner as above to form a green pixel array and a red And pixel arrays are sequentially formed on the same substrate. Thus, 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. In the first method of manufacturing a color filter, at least one of the blue, green, and red pixel arrays may be a colored layer formed using the coloring composition of the present invention.

The black matrix can be formed by forming a thin metal film such as chromium film formed by sputtering or vapor deposition into a desired pattern using a photolithography method. However, by using a radiation-sensitive coloring composition in which a black coloring agent is dispersed , It may be formed in the same manner as in the formation of the pixel. The coloring composition of the present invention can be suitably used also 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, gas 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 employed, A coating method, and a slit die coating method.

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

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

Examples of the light source of radiation 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 argon ion laser, a YAG laser, an XeCl excimer laser, or a nitrogen laser. As an exposure light source, an ultraviolet LED may be used. The wavelength is preferably in the range of 190 to 450 nm.

The exposure dose of radiation is generally preferably from 10 to 10,000 J / m < 2 >.

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

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. Further, after the alkali development, usually water is added.

As the development processing method, a shower development method, a spray development method, a dip (immersion) development method, a puddle development method, or the like can be applied. The development conditions are preferably 5 to 300 seconds at room temperature.

The post-baking conditions are usually about 120 to 280 DEG C for about 10 to 60 minutes, but the post baking temperature is preferably 240 DEG C or less, particularly preferably 230 DEG C or less, more preferably from the standpoint of heat resistance of the present colorant Lt; / RTI >

The film thickness of the pixel thus formed is usually 0.5 to 5 占 퐉, preferably 1 to 3 占 퐉.

As a second method for manufacturing a color filter, there can be employed a method of obtaining a pixel of each color by the ink-jet method disclosed in JP-A-7-318723 and JP-A-2000-310706 have. 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 present invention is ejected by an ink jet apparatus, for example, in which a blue lake pigment is dispersed in the formed barrier ribs, followed by prebaking to evaporate the solvent. Subsequently, this coating film is exposed, if necessary, and then cured by post-baking to form a blue pixel pattern.

Subsequently, a green pixel pattern and a red pixel pattern are sequentially formed on the same substrate by using the green or red colored tandem coloring composition in the same manner as described above. Thereby, a color filter in which pixel patterns 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. Also in the second method of manufacturing a color filter, at least one of the blue, green, and red pixel arrays may be a colored layer formed using the coloring composition of the present invention.

In addition, the barrier ribs have a thicker film thickness than the black matrix used in the first method, because they function not only to shield the light-shielding function but also to prevent coloring compositions of different colors discharged into the compartments from being mixed. Therefore, the barrier ribs are usually 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 in this way is about the same as the height of the partition.

After forming a protective film on the thus-obtained pixel pattern as required, a transparent conductive film is formed by sputtering. After forming the transparent conductive film, a spacer may be further formed to form a color filter. The spacer is usually formed using a radiation sensitive composition, but it may also 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, but the coloring composition of the present invention can be suitably used for forming such a black spacer.

The color filter of the present invention thus obtained is very 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 the present invention comprises the color filter of the present invention. Examples of the display element include a color liquid crystal display element, an organic EL display element, and an electronic paper.

The color liquid crystal display element 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 is formed on a substrate different from a substrate on which a thin film transistor (TFT) is disposed, and a substrate on which a driving substrate and a color filter are formed is opposed via a liquid crystal layer (Indium oxide doped with tin) or IZO (a mixture of indium oxide and zinc oxide), a substrate on which a color filter is formed on the surface of a driving substrate on which a thin film transistor (TFT) The substrate on which the electrodes are formed may have a structure in which the substrates are opposed to each other with the liquid crystal layer interposed therebetween. The latter structure has the advantage that the aperture ratio can be remarkably improved, and a bright, high definition liquid crystal display element can be obtained.

The color liquid crystal display device having the color filter of the present invention can be provided with 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 red light emitting phosphor and a green light emitting phosphor to obtain white light by mixing color, a white LED for obtaining white light by mixing a blue LED and a YAG system phosphor, a blue LED and an isochromatic light emitting phosphor, A white LED for obtaining white light by mixing white light, an ultraviolet LED, a red light emitting phosphor, a green light emitting phosphor and a blue light emitting phosphor to obtain a white light by mixing color.

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) Compensated Birefringence) type liquid crystal mode can be applied.

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 Laid-Open Patent Publication No. 11-307242 is exemplified.

Further, the electronic paper having the color filter of the present invention can adopt a suitable structure. For example, the structure disclosed in Japanese Unexamined Patent Application Publication No. 2007-41169 can be cited.

(Example)

Hereinafter, embodiments of the present invention will be described in more detail with reference to examples. However, the present invention is not limited to the following examples. The abbreviations of the raw materials used in the following examples are as follows.

THF: tetrahydrofuran

nBMA: n-butyl methacrylate

MMA: methyl methacrylate

AMA: Allyl methacrylate

OXMA: 3- (methacryloyloxymethyl) -3-ethyloxetane

THFMA: tetrahydrofurfuryl methacrylate

DAMA: Dimethylaminoethyl methacrylate

PME-200: methoxypolyethylene glycol monomethacrylate (trade name PME-200, manufactured by Nichiyu Co., Ltd., n? 4 in the formula (4)

AIBN: 2,2'-azobisisobutyronitrile

PGMEA: Propylene glycol monomethyl ether acetate

<Synthesis of (B-1) Copolymer>

Synthesis Example 1

Necked flask equipped with a stirrer and thoroughly purged with nitrogen and having an internal volume of 1000 mL was prepared, and under a nitrogen atmosphere, 231 g of toluene, 12 g of 1,2-dimethoxyethane and 0.2 g of diisobutyl (2,6-di -t-butyl-4-methylphenoxy) aluminum in toluene was added. After adjusting the temperature of the contents of the reaction vessel to 0 캜, 4.3 ml of a cyclohexane solution of 1.0 mol / L sec-butyllithium was added, and the mixture was stirred for 20 minutes. To this solution, a mixed solution of 10.5 g of nBMA, 8.1 g of PME-200 and 4.5 g of OXMA was added dropwise over 60 minutes while stirring was maintained at 0 占 폚, and the reaction was further continued for 1 hour. Subsequently, 6.9 g of DAMA was added dropwise over 30 minutes, and the reaction was further continued for 1 hour. After completion of the reaction was confirmed by gas chromatography analysis (hereinafter abbreviated as GC), 0.5 mL of methanol was added to the reaction solution to terminate the polymerization reaction.

Toluene in the obtained solution was removed using a rotary evaporator, and the copolymer was recovered. The recovered copolymer was dissolved in acetone, and the solution was poured into hexane to obtain a precipitate. This operation was repeated five times to carry out purification, and then dried under vacuum at 60 DEG C for 2 hours. Finally, the copolymer was dissolved in PGMEA and adjusted to a solution having a concentration of 40 mass%. Thus, a solution containing a diblock copolymer comprising an A block having a repeating unit derived from DAMA and a B block having repeating units derived from nBMA, PME-200 and OXMA was obtained. The obtained copolymer is referred to as &quot; copolymer (B1) &quot;.

Synthesis Example 2

Necked flask having an internal volume of 500 mL which had been thoroughly purged with nitrogen was charged with 231.0 g of THF and 13.3 mL of a THF solution of 1,1-diphenyl-3-methylpentyllithium at a concentration of 0.25 mol / L . To this solution, a mixed solution of 13.5 g of nBMA, 8.1 g of PME-200 and 1.5 g of OXMA was added dropwise over 60 minutes while being maintained at -70 캜 with stirring, and the reaction was further continued for 1 hour. Subsequently, 6.9 g of DAMA was added dropwise over 30 minutes, and the reaction was further continued for 1 hour. After completion of the reaction was confirmed by GC, 0.5 mL of methanol was added to the reaction solution to terminate the polymerization reaction.

The resulting solution was poured into 1.5 L of hexane to precipitate the resulting copolymer and recovered. Further, the recovered copolymer was dissolved in methanol, and then the solution was poured into hexane. This operation was repeated five times to carry out purification, and then dried under vacuum at 60 DEG C for 2 hours. Finally, the copolymer was dissolved in PGMEA to prepare a solution having a concentration of 40% by mass. Thus, a solution containing a diblock copolymer comprising an A block having a repeating unit derived from DAMA and a B block having repeating units derived from nBMA, PME-200 and OXMA was obtained. The obtained copolymer is referred to as &quot; copolymer (B2) &quot;.

Synthesis Example 3

30 g of toluene, 12.0 g of nBMA, 10.9 g of PME-200, 3.4 g of THFMA, 236 mg of AIBN and 608 mg of cyano (dimethyl) methyl ester of pyrazole-1-dithiocarboxylic acid were added to and dissolved in a 300 mL flask equipped with a stirrer. Nitrogen substitution was carried out. Thereafter, the mixture was gently stirred to raise the temperature of the reaction solution to 60 DEG C, and this temperature was maintained for 24 hours to perform living radical polymerization.

Subsequently, 410 mg of AIBN and 7.9 g of DAMA were dissolved in 20 g of toluene, and the solution was subjected to nitrogen substitution for 30 minutes. The solution was added to the reaction solution and subjected to living radical polymerization at 60 DEG C for 24 hours. Thereafter, the solution was adjusted to a 40% by mass concentration of PGMEA solution by concentration under reduced pressure. Thus, a solution containing a diblock copolymer consisting of an A block having a repeating unit derived from DAMA and a B block having repeating units derived from nBMA, PME-200 and THFMA was obtained. The obtained diblock copolymer is referred to as &quot; copolymer (B3) &quot;.

Synthesis Example 4

To the 300 mL flask equipped with a stirrer was added 30 g of toluene, 8.8 g of MMA, 7.9 g of PME-200, 2.9 g of OXMA, 217 mg of AIBN and 559 mg of pyrazole-1-dithiocarboxylic acid cyano (dimethyl) methyl ester, Nitrogen substitution was carried out. Thereafter, the mixture was gently stirred to raise the temperature of the reaction solution to 60 DEG C, and this temperature was maintained for 24 hours to perform living radical polymerization.

Subsequently, 504 mg of AIBN and 9.7 g of DAMA were dissolved in 20 g of toluene, and the solution was subjected to nitrogen substitution for 30 minutes. The resulting solution was subjected to living radical polymerization at 60 DEG C for 24 hours. Thereafter, the solution was adjusted to a 40% by mass concentration of PGMEA solution by concentration under reduced pressure. Thus, a solution containing a block A having a repeating unit derived from DAMA and a diblock copolymer comprising a repeating unit derived from MMA, PME-200 and OXMA and a B block was obtained. The obtained diblock copolymer is referred to as &quot; copolymer (B4) &quot;.

Synthesis Example 5

To a 300 mL flask equipped with a stirrer was added 30 g of toluene, 10.2 g of MMA, 6.9 g of nBMA, 3.3 g of PME-200, THFMA 1.3 g, 278 mg of AIBN and 716 mg of cyano (dimethyl) methyl ester of pyrazole- And nitrogen replacement was carried out for 30 minutes. Thereafter, the mixture was gently stirred to raise the temperature of the reaction solution to 60 DEG C, and this temperature was maintained for 24 hours to perform living radical polymerization.

Subsequently, 199 mg of AIBN and 3.8 g of DAMA were dissolved in 20 g of toluene, and the solution was subjected to nitrogen substitution for 30 minutes. The solution was added to the reaction solution, and subjected to living radical polymerization at 60 DEG C for 24 hours. Thereafter, the solution was adjusted to a 40% by mass concentration of PGMEA solution by concentration under reduced pressure. Thus, a solution containing a diblock copolymer comprising an A block having a repeating unit derived from DAMA and a B block having repeating units derived from MMA, nBMA, PME-200 and THFMA was obtained. The obtained diblock copolymer is referred to as &quot; copolymer (B5) &quot;.

Synthesis Example 6

30 g of toluene, 8.0 g of nBMA, 3.2 g of PME-200, 6.4 g of OXMA, 168 mg of AIBN and 433 mg of cyano (dimethyl) methyl ester of pyrazole-1-dithiocarboxylic acid were added and dissolved in a 300 mL flask equipped with a stirrer. Nitrogen substitution was carried out. Thereafter, the mixture was gently stirred to raise the temperature of the reaction solution to 60 DEG C, and this temperature was maintained for 24 hours to perform living radical polymerization.

Subsequently, 749 mg of AIBN and 14.4 g of DAMA were dissolved in 20 g of toluene, and the solution was subjected to nitrogen substitution for 30 minutes. The solution was added to the reaction solution and subjected to living radical polymerization at 60 DEG C for 24 hours. Thereafter, the solution was adjusted to a 40% by mass concentration of PGMEA solution by concentration under reduced pressure. Thus, a solution containing a diblock copolymer comprising an A block having a repeating unit derived from DAMA and a B block having repeating units derived from nBMA, PME-200 and OXMA was obtained. The obtained diblock copolymer is referred to as &quot; copolymer (B6) &quot;.

Comparative Synthesis Example 1

The procedure of Synthesis Example 2 was repeated, except that a mixed solution of 13.5 g of nBMA, 8.1 g of PME-200 and 1.5 g of OXMA was changed to a mixed solution of 15.0 g of nBMA and 8.1 g of PME-200, A 40% by mass concentration PGMEA solution containing a diblock copolymer comprising an A block having repeating units derived from DAMA and a B block having repeating units derived from nBMA and PME-200, . The obtained diblock copolymer is referred to as &quot; copolymer (b1) &quot;.

Comparative Synthesis Example 2

Except that the mixed solution of 13.5 g of nBMA, 8.1 g of PME-200 and 1.5 g of OXMA was changed to a mixed solution of 10.5 g of nBMA, 8.1 g of PME-200 and 4.5 g of AMA, In the same manner, a diblock copolymer was synthesized, and 40 mass parts of a block copolymer containing a diblock copolymer composed of an A block having a repeating unit derived from DAMA and a B block having repeating units derived from nBMA, PME-200 and AMA % Concentration of PGMEA solution. The obtained diblock copolymer is referred to as &quot; copolymer (b2) &quot;.

Comparative Synthesis Example 3

30 g of toluene, 8.7 g of MMA, 7.8 g of PME-200, 188 mg of AIBN and 485 mg of cyano (dimethyl) methyl ester of pyrazole-1-dithioic acid were added and dissolved in a 300 mL flask equipped with a stirrer, . Thereafter, the mixture was gently stirred to raise the temperature of the reaction solution to 60 DEG C, and this temperature was maintained for 24 hours to perform living radical polymerization.

Subsequently, 647 mg of AIBN and 12.4 g of DAMA were dissolved in 20 g of toluene, and the solution was subjected to nitrogen substitution for 30 minutes. The solution was added to the reaction solution and subjected to living radical polymerization at 60 DEG C for 24 hours. Thereafter, the solution was adjusted to a 40% by mass concentration of PGMEA solution by concentration under reduced pressure. Thus, a solution containing a diblock copolymer consisting of an A block having a repeating unit derived from DAMA and a B block having repeating units derived from MMA and PME-200 was obtained. The obtained diblock copolymer is referred to as &quot; copolymer (b3) &quot;.

Comparative Synthesis Example 4

30 g of toluene, 8.2 g of MMA, 11.5 g of nBMA, 6.3 g of PME-200, 303 mg of AIBN and 782 mg of cyano (dimethyl) methyl ester of pyrazole-1-dithiocarboxylic acid were added to and dissolved in a 300 mL flask equipped with a stirrer. Nitrogen substitution was performed for a minute. Thereafter, the mixture was gently stirred to raise the temperature of the reaction solution to 60 DEG C, and this temperature was maintained for 24 hours to perform living radical polymerization.

Subsequently, 71 mg of AIBN and 1.4 g of DAMA were dissolved in 20 g of toluene, and the solution was subjected to nitrogen substitution for 30 minutes. The solution was added to the reaction solution, and subjected to living radical polymerization at 60 ° C for 24 hours. Thereafter, the solution was adjusted to a 40% by mass concentration of PGMEA solution by concentration under reduced pressure. Thus, a solution containing a diblock copolymer comprising an A block having a repeating unit derived from DAMA and a B block having repeating units derived from MMA, nBMA and PME-200 was obtained. The obtained diblock copolymer is referred to as &quot; copolymer (b4) &quot;.

<Measurement of Mw and Mw / Mn of (B-1) Copolymer>

Mw and Mn of the (B-1) copolymer obtained in each of the above Synthesis Examples are shown in Table 1 together with the copolymerization ratio (mass%) of each monomer. Mw and Mn were measured by GPC of the following specifications.

Apparatus: GPC-104 (manufactured by Showa Denko K.K.)

Column: KD-G, KF-603, KF-602, KF-601 (manufactured by Showa Denko K.K.)

Mobile phase: DMF

<Measurement of Amine Value of (B-1) Copolymer>

The amine value of the (B-1) copolymer obtained in each of the above Synthesis Examples was measured in the following manner. Table 1 shows the measurement results.

0.5 g of the copolymer solution was precisely weighed to a unit of 1 mg and divided into glass (glass) containers. 20 mL of anhydrous acetic acid / acetic acid = 9/1 (volume ratio) was added and dissolved, and the mixture was allowed to stand at room temperature for 3 hours. Thereafter, 30 mL of acetic acid was further added, and titration was performed with a 0.1 mol / L perchloric acid / acetic acid solution using a potential difference measuring device AT-510 (manufactured by Kyoto Denshi Co., Ltd.). The same blank test was conducted. (Unit: mgKOH / g) was calculated from the drop amount of 0.1 mol / L perchloric acid / acetic acid solution of the (B-1) copolymer and the blank test.

&Lt; (D) Synthesis of binder resin >

Synthesis Example 7

In a flask equipped with a cooling tube and a stirrer, 100 parts by mass of PGMEA was placed and replaced with nitrogen. And the mixture was heated at 80 占 폚, and at the same temperature, 100 parts by mass of PGMEA, 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) in an amount of 6 parts by mass was added dropwise over one hour, and the temperature was maintained and maintained 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). The obtained binder resin had Mw of 12,200, Mn of 6,500, and Mw / Mn of 1.87 in terms of polystyrene measured by GPC (mobile phase: THF). This binder resin is referred to as &quot; binder resin (D1) &quot;.

Synthesis Example 8

To a flask equipped with a cooling tube and a stirrer were added 30.0 g of benzyl methacrylate, 20.0 g of nBMA, 15.0 g of hydroxyethyl methacrylate, 20.0 g of styrene, 15.0 g of methacrylic acid and 200 g of PGMEA, And 5.0 g of? -Methylstyrene dimer were charged, and then the atmosphere was replaced with nitrogen for 15 minutes. Thereafter, the reaction solution was heated to 80 캜 with stirring and polymerized for 5 hours to obtain a binder resin solution (solid content concentration: 33% by mass). The binder resin had Mw of 10,000, Mn of 4,000 and Mw / Mn of 2.5 as measured by GPC (mobile phase: THF) in terms of polystyrene. This binder resin is referred to as &quot; binder resin (D2) &quot;.

&Lt; Preparation of pigment dispersion containing (B-1) copolymer >

Preparation Example 1

12 parts by mass of the triarylmethane lake pigment (x = 1 to 2) represented by the following formula (6) as the coloring agent, 10 parts by mass of the copolymer (B1) solution (nonvolatile component = 40% by mass) , 73 parts by mass of PGMEA and 5 parts by mass of propylene glycol monomethyl ether were treated with a bead mill to prepare a pigment dispersion (A-1).

Preparation Examples 2 to 6 and Comparative Preparation Examples 1 to 4

Pigment dispersions (A-2) to (A-10) were prepared in the same manner as in Preparation Example 1 except that the kind of the copolymer (B-1) in Preparation Example 1 was changed as shown in Table 2 .

Preparation Example 7

As a colorant, C.I. Pigment Red 254 / C.I. Pigment Red 177 / C.I. 12 mass parts of a mixture of Pigment Red 81: 2 (xanthane lake pigment laked with silicomolybdic acid) = 10/70/20 (mass ratio), 10 mass parts of a copolymer (B1) solution (nonvolatile component = 40 mass , 73 parts by mass of PGMEA as a solvent and 5 parts by mass of propylene glycol monomethyl ether were used and treated with a bead mill to prepare a pigment dispersion (A-11).

Preparation Examples 8 and 9 and Comparative Preparation Examples 5 and 6

Pigment dispersions (A-12) to (A-15) were prepared in the same manner as in Preparation Example 7 except that the kind of the copolymer (B-1) in Preparation Example 7 was changed as shown in Table 2 .

<Preparation and Evaluation of Coloring Composition Containing (B-1) Copolymer>

Example 1

100 parts by mass of the pigment dispersion (A-1), 52.9 parts by mass of a binder resin (D2) solution as a binder resin, and MAX-3510 (dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate, manufactured by Nippon Kayaku Co., , 32.9 parts by mass of dipentaerythritol hexaacrylate as a main component), 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one as a photopolymerization initiator (IRGACURE 369, manufactured by Chiba Specialty Chemicals), and 205.2 parts by mass of PGMEA as a solvent were mixed to prepare a liquid color composition (S-1).

The resulting colored composition (S-1) was applied on a soda glass substrate having a SiO ₂ film formed on its surface to prevent the dissolution of sodium ions using a spin coater, and then pre-baked on a hot plate at 90 캜 for 2 minutes To form a coating film having a thickness of 2.5 mu m.

Subsequently, after cooling the substrate to room temperature, radiation containing each wavelength of 365 nm, 405 nm, and 436 nm was exposed to an exposure amount of 400 J / m &lt; 2 &gt; through a photomask using a high pressure mercury lamp, did. Thereafter, a showering phenomenon was carried out for 90 seconds on the substrate by discharging a developing solution composed of 0.04 mass% potassium hydroxide aqueous solution at 23 占 폚 at a developing pressure of 1 kgf / cm2 (nozzle diameter of 1 mm). Thereafter, this substrate was washed with ultrapure water, air-dried, and further baked in a clean oven at 200 캜 for 30 minutes to form a dot pattern of 200 탆 x 200 탆 on the substrate.

Evaluation of heat resistance

The chromaticity coordinate value (x, y) and the magnetic pole value (Y) in the CIE colorimetric system in the C light source and in the 2-degree field are calculated using the color analyzer (MCPD2000 manufactured by Otsuka Denshi Co., Respectively. Then, the chromaticity coordinate value (x, y) and the magnetic pole value (Y) after further baking at 200 DEG C for 90 minutes were measured to evaluate the color change before and after further baking, i.e., DELTA E ^* _ab . The evaluation results are shown in Table 3. Further, the smaller the value of? E ^* _ab, the higher the heat resistance.

Solvent-resistant  evaluation

The substrate on which the blue dot pattern was formed was immersed in N-methylpyrrolidone at 25 占 폚 for 30 minutes, and the dot pattern before and after immersion was observed with a scanning electron microscope. Good ", and the film thickness ratio before and after immersion (film thickness after immersion × 100 / film thickness before immersion) was 95% or more," ○ ", the film thickness ratio before and after immersion was less than 95% &Quot; DELTA &quot; when a defect was found in a part of the pattern, and &quot; x &quot; when the pattern was completely peeled off the substrate after immersion. The evaluation results are shown in Table 3.

Examples 2 to 9 and Comparative Examples 1 to 6

The preparation and evaluation of the colored composition were carried out in the same manner as in Example 1 except that the kind of the pigment dispersion was changed as shown in Table 3 in Example 1. The evaluation results are shown in Table 3.

Preparation and evaluation of a coloring composition comprising (B-2) a dispersing agent having a urethane bond and (B-3) a (meth) acrylic dispersing agent [

Example 10

15 mass parts of a triarylmethane lake pigment (where x = 1 to 2) represented by the formula (6) shown above as a colorant, BYK2164 (nonvolatile component = 60 mass%, amine value 14 mgKOH / g, BYK), 1.8 parts by mass of BYK-LPN21116 (nonvolatile component = 40% by mass, amine value of 29 mgKOH / g, manufactured by BYK Corporation) as a (meth) acrylic dispersant, and 1.8 parts by mass of propylene glycol monomethyl A mixed solvent of ether acetate / propylene glycol monoethyl ether = 90/10 (mass ratio) was mixed so as to have a solid content concentration of 20 mass% and mixed and dispersed for 12 hours by a bead mill to prepare a pigment dispersion (M-1) .

Next, 13.5 parts by mass of the pigment dispersion (M-1), 9.9 parts by mass of a binder resin (D1) solution as a binder resin, and M-402 (dipentaerythritol hexaacrylate and dipentaerythritol penta Acrylate), 1.8 parts by mass of 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one (trade name IRGACURE369, manufactured by Ciba Specialty Chemicals Inc.) as a photopolymerization initiator , 0.2 part by mass of MEGAFAC F-554 (manufactured by DIC Corporation) as a fluorine surfactant, and propylene glycol monomethyl ether acetate as a solvent were mixed to prepare a coloring composition (CR1) having a solid content concentration of 20 mass% .

Except that the coloring composition (CR1) was used in place of the coloring composition (S-1) and the time for pre-baking was changed to 4 minutes in Example 1, To form a coating film.

Subsequently, in the same manner as in Example 1, a dot pattern of 200 mu m x 200 mu m was formed on the substrate.

The obtained dot pattern was evaluated for heat resistance and solvent resistance in the same manner as in Example 1. The evaluation results are shown in Table 5. However, the evaluation by the not less than In, ΔE _ab * is the "△", 10 if the case a is less than "◎", 3.0, 5.0 or less than 3.0 "○", 5.0 or more and less than 10, the evaluation of the heat resistance by "×." did.

Examples 11 to 20 and Comparative Examples 7 to 10

The procedure of Example 10 was repeated to prepare a pigment dispersion (M-2) from the pigment dispersion (M-2) in the same manner as in Example 10, except that the kind and blending amount of the colorant, urethane- M-15) was prepared.

Next, the same procedure as in Example 10 was carried out except that the pigment dispersions (M-2) to (M-15) were used instead of the pigment dispersions (M-1) CR15) was prepared. The obtained coloring composition was evaluated in the same manner as in Example 10. The evaluation results are shown in Table 5.

In Table 4, the respective components are as follows.

&Quot; PB61 &quot; Pigment Blue 61, and &quot; PB15: 6 &quot; Pigment Blue 15: 6, and &quot; PR254 &quot; Pigment Red 254, and &quot; PR81: 2 &quot; Pigment Red 81: 2 (xanthene lake pigment laked with silicomolybdic acid), respectively.

BYK2164 "refers to Disperbyk-2164 (nonvulcan component = 60 mass%, amine value 14 mgKOH / g, manufactured by BYK), Disperbyk-164 (nonvulcan component = 60 mass%, amine value 18 mgKOH / g, manufactured by BYK), and S76500 (solder pulse 76500 (nonvolatile component = 50 mass%, amine value 15 mgKOH / g, manufactured by Lubrizol Corporation).

(Nonvolatile component = 40 mass%, amine value = 4 mg KOH / g, manufactured by BYK), BYK-LPN21116 (nonvolatile component = 40 mass% g and BYK-LPN6919 (nonvolatile component = 60% by mass, amine value: 72 mgKOH / g, manufactured by BYK) respectively as "LPN6919".

Claims (12)

1. A colored composition comprising (A) a colorant containing a lake pigment, (B) a dispersant, and (C) a crosslinking agent, wherein (B) a copolymer comprising a repeating unit having an oxygen-containing saturated heterocyclic group (B- &Lt; / RTI &gt; The method according to claim 1,
Wherein the (B-1) copolymer further has a repeating unit represented by the following formula (1) and a repeating unit represented by the following formula (2);

[In the formula (1)
R ¹ represents a hydrogen atom or a methyl group,
Z represents -NR ² R ³ (wherein R ² and R ³ independently represent a hydrogen atom or a substituted or unsubstituted hydrocarbon group) or a substituted or unsubstituted nitrogen-containing heterocyclic group,
X ¹ represents a divalent linking group;

[In the formula (2)
R ⁴ represents a hydrogen atom or a methyl group,
And R ⁵ represents an aliphatic hydrocarbon group or an alicyclic hydrocarbon group. 3. The method of claim 2,
The upper limit of the amine value of the (B-1) copolymer is 150 mgKOH / g. delete delete The method according to claim 1,
Wherein the rake pigment is prepared using heteropoly acid. The method according to claim 1,
Wherein the rake pigment is at least one selected from a triarylmethane lake pigment and a zottenic lake pigment. The method according to claim 1,
Wherein the coloring composition further comprises a pigment (excluding a lake pigment) as the coloring agent (A). The method according to claim 1,
(D) a binder resin (excluding the above component (B)). A color filter comprising a colored layer formed using the coloring composition according to any one of claims 1 to 3 and 6 to 9. A display device comprising the color filter according to claim 10. A pigment dispersion containing (a1) a lake pigment, (B-1) a copolymer comprising a repeating unit having an oxygen-containing saturated heterocyclic group, and (F) a solvent.