KR101980919B1 - Colorant, coloring composition for color filter, color filter and display device - Google Patents

Abstract

An object of the present invention is to provide a coloring composition having a high tinting strength and being suitable for the formation of a coloring layer having high heat resistance and excellent chromaticity characteristics.
A solving means of the present invention is a coloring composition for a color filter containing (A) a colorant, (B) a binder resin and (C) a crosslinking agent, and is characterized by containing (A) an acidic colorant having a phosphonium cation as a colorant To provide a coloring composition.

Description

COLORING COMPOSITION, COLOR FILTER AND DISPLAY DEVICE, COLOR FILTER, AND DISPLAY DEVICE [0002]

The present invention relates to a coloring agent, 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 element, A coloring composition containing the coloring agent, a color filter including the coloring layer containing the coloring agent, and a display element including 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 a desired pattern (hereinafter, (Patent Literatures 1 and 2), in which pixels of each color are obtained. Further, a method of forming a black matrix using a photopolymerizable composition in which carbon black is dispersed (Patent Document 3) is also known. There is also known a method of obtaining pixels of respective colors by an ink jet method using a pigment dispersion type colored resin composition (Patent Document 4).

However, it is known that it is effective to use a dye as a coloring agent in order to realize high brightness and high color purity of a display element or high-definition of a solid-state image pickup element. For example, in Patent Document 5, it has been reported that by using a xanthene dye having a specific structure, it is possible to form a color filter capable of achieving both chromaticity characteristics and heat resistance.

Japanese Patent Application Laid-Open No. 2-144502 Japanese Patent Laid-Open Publication No. 3-53201 Japanese Patent Application Laid-Open No. 6-35188 Japanese Patent Application Laid-Open No. 2000-310706 Japanese Patent No. 4492760 Specification

However, according to the investigations of the present inventors, it has been found that the use of the specific xanthene dye proposed in Patent Document 5 is not necessarily preferable for the formation of the color filter because the coloring power is low.

Accordingly, an object of the present invention is to provide a coloring composition which is high in coloring power and is suitable for forming a coloring layer having high heat resistance and excellent coloring characteristics. It is still another object of the present invention to provide a coloring agent capable of obtaining the coloring composition, a color filter comprising the coloring layer containing the coloring agent, and a display element comprising the coloring filter.

In view of such circumstances, the inventors of the present invention have made extensive studies, and have found that the above problems can be solved by using a colorant having a specific structure.

That is, the present invention relates to a coloring composition for a color filter comprising (A) a colorant, (B) a binder resin and (C) a crosslinking agent, wherein the coloring composition comprises (A) an acidic colorant having a phosphonium cation as a colorant To provide a composition.

The present invention also provides a color filter comprising a colored layer containing an acidic colorant having a phosphonium cation and a display element comprising the color filter. Here, the " colored layer " means each color pixel, a black matrix, a black spacer, and the like used in the color filter.

The present invention also provides an acidic colorant having a phosphonium cation.

By using the coloring composition for a color filter of the present invention, it is possible to form a colored layer having high coloring power, high heat resistance and excellent coloring characteristics. Therefore, the coloring composition for a color filter of the present invention is highly 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.

Hereinafter, the present invention will be described in detail.

color Filter coloring Composition

Hereinafter, the constituent components of the coloring composition for a color filter of the present invention (hereinafter, simply referred to as "coloring composition") will be described in detail.

- (A) Colorant -

The coloring composition of the present invention contains an acidic coloring agent having a phosphonium cation as a coloring agent (hereinafter also referred to as " main coloring agent "). The acidic coloring agent is an ionic coloring agent in which the anion portion is a chromophore. In this coloring agent, the anion portion constituting the chromophore and the phosphonium cation form a salt.

First, the phosphonium cations constituting the present colorant will be described.

The phosphonium cation in the present invention is a concept encompassing a cation structure charged with a positive valence of a valence of 4 atoms, and the structure thereof is not particularly limited as long as it has a cation centered on a phosphorus atom. Specifically, the following can be mentioned.

(i) A monovalent phosphonium cation having one phosphorus atom as a cation center in a single structure.

(ii) a multivalent phosphonium cation having as a cation center at least two phosphorus atoms in a single structure.

(iii) multivalent cations having a phosphorus atom and an atom other than phosphorus as a cation center in a single structure. Examples of the atom constituting the cation center including an atom other than phosphorus include a nitrogen atom and the like.

(iv) a cation having a cation center containing a phosphorus atom in a single structure, a cation center comprising an arbitrary atom and an anion center comprising an arbitrary atom, and positively charged throughout the structure.

Of these, the above-mentioned (i), (ii) and (iii) are preferable from the viewpoint of easiness of obtaining the raw material, and the above-mentioned (i) and (ii) are more preferable.

Examples of preferred phosphonium cations in the present invention include cations represented by the following formulas (1) and (2).

[In the formula (1)

R ¹ to R ⁴ independently represent a hydrogen atom or an organic group, provided that at least one of R ¹ to R ⁴ is an organic group and two of R ¹ to R ⁴ may be bonded to form a ring]

[In the formula (2)

R ⁵ to R ¹⁰ independently represent a hydrogen atom or an organic group, provided that two of R ⁵ to R ¹⁰ may be bonded to form a ring;

X represents a divalent linking group].

Examples of the organic groups in R ¹ to R ⁴ include a hydrocarbon group, and more specifically, (1) an aliphatic hydrocarbon group, (2) an alicyclic hydrocarbon group, (3) an aliphatic hydrocarbon group having an alicyclic hydrocarbon group (4) an aromatic hydrocarbon group, (5) an aromatic hydrocarbon group having an aliphatic hydrocarbon group as a substituent (hereinafter also referred to as an "aliphatic hydrocarbon-substituted aromatic hydrocarbon group"), ( 6) an aliphatic hydrocarbon group having an aromatic hydrocarbon group as a substituent (hereinafter also referred to as an " aromatic hydrocarbon-substituted aliphatic hydrocarbon group "). The number of carbon atoms constituting the hydrocarbon group is preferably from 1 to 30.

Examples of the aliphatic hydrocarbon group (1) include an alkyl group, an alkenyl group and an alkynyl group. These aliphatic hydrocarbon groups preferably have 1 to 30 carbon atoms, more preferably 1 to 24 carbon atoms, and particularly preferably 1 to 20 carbon atoms. These aliphatic hydrocarbon groups may be linear or branched. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a hexyl group, a heptyl group, A pentadecyl group, a 1-heptyloctyl group, a 1-hexadecyl group, a 1-methyldecyl group, a 1-methyldecyl group, Hexadecyl group, and octadecyl group. Examples of the alkenyl group include an ethynyl group, an 1-propenyl group, a 2-propenyl group, a 1-butenyl group, (2-ethyl-2-butenyl group, 2-octenyl group, (4-ethenyl) -5-hexenyl group and 2-decenyl group. Examples of the alkynyl group include an ethynyl group, a 1-propynyl group, a 1-butynyl group, a 1-pentynyl group, a 3-pentynyl group, a 1-hexynyl group, , (4-ethynyl) -5-hexynyl, 2-decynyl and the like.

The alicyclic hydrocarbon group (2) is preferably an alicyclic hydrocarbon group having 3 to 30 carbon atoms. Specific examples of the alicyclic hydrocarbon group 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. More specifically, a cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a t-butylcyclohexyl group, a cycloheptyl group, and a cyclooctyl group; A cycloalkenyl group such as a 1-cyclohexenyl group; Condensed polycyclic hydrocarbon groups such as a tricyclodecanyl group, a decahydro-2-naphthyl group and an adamantyl group; A bridged ring hydrocarbon group such as a tricyclo [5.2.1.0 ^2,6 ] decan-8-yl group, a pentacyclopentadecanyl group, an isobornyl group, a dicyclopentenyl group and a tricyclopentenyl group; A spiro hydrocarbon group such as spiro [3,4] heptane, or a monovalent group obtained by removing one hydrogen atom from spiro [3,4] octane; and a cyclic terpene hydrocarbon group such as a monovalent group obtained by removing one hydrogen atom from p-menthane, toluene, and carane. The cycloalkyl group and the cycloalkenyl group preferably have 3 to 12 carbon atoms.

The (3) alicyclic hydrocarbon-substituted aliphatic hydrocarbon group is preferably an alkyl group substituted with an alicyclic saturated hydrocarbon group. The total carbon number of the alicyclic hydrocarbon-substituted aliphatic hydrocarbon group is preferably 4 to 20, more preferably 6 to 14. Specific examples thereof include a cyclopropylmethyl group, a cyclobutylmethyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, and a cyclohexylethyl group.

The aromatic hydrocarbon group (4) preferably has 6 to 20 carbon atoms, more preferably 6 to 10 carbon atoms. Specific examples of the aromatic hydrocarbon group include an aryl group. Herein, in the present invention, the "aryl group" refers to a monocyclic to tricyclic aromatic hydrocarbon group, and specific examples thereof include phenyl group, naphthyl group, anthryl group, phenanthryl group, azulenyl group, 9- have. Among them, a phenyl group, a naphthyl group and a 9-fluorenyl group are preferable from the viewpoint of easiness of obtaining a raw material.

The aliphatic hydrocarbon-substituted aromatic hydrocarbon group (5) preferably has 7 to 30 carbon atoms in total, and more preferably 7 to 20 carbon atoms. Specifically, an alkyl-substituted aryl group can be exemplified, and an alkyl-substituted phenyl group and the like are preferable. Specific examples include o-tolyl group, m-tolyl group, p-tolyl group, and xylyl group.

The aromatic hydrocarbon-substituted aliphatic hydrocarbon group (6) preferably has 7 to 30 carbon atoms in total, and more preferably 7 to 20 carbon atoms. Specific examples include a benzyl group, a 2-phenylethyl group (phenethyl group), a 3-phenylpropyl group, a 1-naphthylmethyl group and a cinnamyl group.

Examples of the organic groups represented by R ¹ to R ⁴ include heterocyclic groups, acetonyl groups, and phenacyl groups in addition to the hydrocarbon groups represented by (1) to (6). As the heterocyclic group, a monovalent heterocyclic group having 3 to 10 carbon atoms is preferable, and specific examples thereof include a pyrrolidinyl group, an imidazolidinyl group, a pyrazolidinyl group, a piperidyl group, a piperidino group, a piperazinyl group, An alicyclic heterocyclic group such as a morpholinyl group, a morpholinyl group, a thiomorpholinyl group and a 1,3-dioxolan-2-yl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, A pyrrolyl group, an imidazolyl group, a pyrazolyl group, a triazoyl group, a tetrazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, An aromatic heterocyclic group such as a benzoimidazolyl group, a pyridyl group, a phthalimide group and the like can be mentioned.

The organic groups in R ¹ to R ⁴ may further have a substituent within the scope of the present invention. The position and the number of the substituent are arbitrary, and when two or more substituents are present, the substituents may be the same or different. Examples of the substituent include a halogen atom, a hydroxyl group, a cyano group, a formyl group, a carboxyl group, a nitro group, an amino group, a dialkylamino group, a diarylamino group, an alkoxy group, an alkoxycarbonyl group, an alkylthio group, , And a heterocyclic group.

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. Examples of the dialkylamino group include a dimethylamino group and a diethylamino group, and a diarylamino group includes a diphenylamino group. Examples of the alkoxy group include methoxy group, ethoxy group, propoxy group and butoxy group. Examples of the alkoxycarbonyl group include methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group and butoxycarbonyl group. Examples of the alkylthio group include a methylthio group and an ethylthio group, and an arylthio group includes a phenylthio group. Examples of the trialkylsilyl group include a trimethylsilyl group and the like. The heterocyclic group may be the same as described above.

Two of the organic groups in R ¹ to R ⁴ may be bonded to each other to form a ring. Specifically, (1-i) the R ¹ and R ² combine with each other to form a ring, R ³ and R ⁴ are the case does not form a ring, ^(1-ii) R 1 and R ² are bonded to each other And a case where R < ³ > and R < ⁴ > are bonded to each other to form a second ring can be used as the phosphonium cation of the present colorant. Among them, the case of (1-i) is preferable from the viewpoint of easiness of obtaining the raw material.

At least one of R ¹ to R ⁴ is the organic group, in view of ease of the coloring composition stability and material availability, at least three of R ¹ to R ⁴ are more preferably preferably an organic group, and 4, all the organic group , And it is particularly preferable that all four are hydrocarbon groups. The total carbon number constituting R ¹ to R ⁴ is preferably 5 to 50, and particularly preferably 10 to 40. By using R ¹ to R ⁴ in this embodiment, a colorant capable of forming a pixel having good solubility in an organic solvent, tinting power, and high contrast ratio can be obtained.

In the formula (2), as organic groups in R ⁵ to R ¹⁰ , the same groups as the organic groups in R ¹ to R ⁴ can be adopted. Its concrete structure is as described above. The organic group in R ⁵ to R ¹⁰ may further have a substituent, and the substituent may be the same as the substituent which the organic group in R ¹ to R ⁴ may have.

Two of the organic groups in R ⁵ to R ¹⁰ may be bonded to each other to form a ring. Specifically, when (2-i) R ⁵ and R ⁶ are bonded to each other to form a ring, and R ⁷ to R ¹⁰ do not form a ring, (2-ii) R ⁵ and R ⁶ bond to each other (2-iii) when R ⁵ and R ¹⁰ are bonded to each other to form a first ring, R ⁸ and R ⁹ are bonded to each other to form a second ring, and when R ⁷ and R ¹⁰ do not form a ring, And R ⁶ to R ⁹ do not form a ring, all of which can be used as a phosphonium cation of the present colorant. Among them, the case of (2-i) is preferable from the viewpoint of easiness of obtaining a raw material.

From the standpoints of the stability of the coloring composition and the ease of obtaining the raw materials, the organic groups represented by R ⁵ to R ¹⁰ are preferably R ⁵ To at least two of R ⁷ is an organic group, R ⁸ to R ¹⁰ and at least two of the organic group to be preferred, and 6 all organic group of R ⁵ to R ¹⁰ are particularly preferred.

Examples of the divalent linking group in X include an alkanediyl group, an alkenediyl group, a 1,4-phenylenebis (alkanediyl) group, an oxy group, an oxyalkanedioxy group, and an alkanedioxyalkanediyl group .

The alkanediyl group preferably has 1 to 10 carbon atoms. 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, Hexane-1,5-diyl group, hexane-1,6-diyl group, octane-1,8-diyl group, decane-1,10-diyl group and the like. Among them, an alkanediyl group having 1 to 8 carbon atoms is preferable, and an alkanediyl group having 1 to 6 carbon atoms is more preferable, and a methylene group, an ethylene group, a propane-1,3-diyl group, A di-yl group, a pentane-1,5-diyl group, and a hexane-1,6-diyl group.

As the alkenediyl group, those having 2 to 10 carbon atoms are preferable, and specific examples thereof include ethene-1,1-diyl group, ethene-1,2-diyl group, propene-1,2-diyl group, 1-butene-1, 3-diyl group, 1-butene-1, 4-diyl group, 2-pentene -1,5-diyl group, 3-hexene-1,6-diyl group and the like.

The 1,4-phenylenebis (alkanediyl) group is a group in which alkandiyl groups are bonded to both ends of the 1,4-phenylene group, and the total carbon number of the 1,4-phenylenebis (alkandiyl) group is 8 To 10 is preferable. Specific examples thereof include 1,4-phenylenebis (methylene) group and 1,4-phenylenebis (ethylene) group.

The oxyalkanediyloxy group is a group in which oxygen atoms are bonded to both terminals of the alkanediyl group, and the total number of carbon atoms of the oxyalkanedioxy group is preferably 1 to 10. Specific examples thereof include an oxymethyleneoxy group, oxyethyleneoxy group, oxytrimethyleneoxy group, oxypropane-1,2-diyloxy group, oxytetramethyleneoxy group and the like.

The alkanedioxyalkanediyl group is a group in which two alkanediyl groups are bonded through an oxygen atom, and the total carbon number of the alkanedioxyanedanyl group is preferably from 2 to 20. [ Specific examples thereof include a methyleneoxymethylene group, an ethyleneoxyethylene group, a trimethyleneoxytrimethylene group, an ethyleneoxytrimethylene group, a propane-1,2-diyloxypropane-1,2-diyl group, an ethyleneoxypropane- A 2-diyl group, and a tetramethyleneoxytetramethylene group.

Examples of the cation represented by the above formula (1) or (2) include the following cations represented by the following group of compounds? To?.

Next, the anion part constituting the chromophore of the present colorant will be described. The anion moiety of the present colorant is not particularly limited as long as it is a chromophore having an anionic functional group such as -SO ₃ ^- or -COO ^- , but is preferably a chromophore having -SO ₃ ^- .

In the present invention, various chromophores can be used as the chromophores. As the chromophore in the present invention, for example, there may be mentioned a chroman-based chromophore having an anionic functional group, a triarylmethane chromophore having an anionic functional group, an azo chromophore having an anionic functional group, an anthraquinone chromophore having an anionic functional group, A phthalocyanine chromophore having an anionic functional group, a quinoline chromophore having an anionic functional group, an azine chromophore having an anionic functional group, an acridine chromophore having an anionic functional group, an anionic functional group having an anionic functional group Indigo-based chromophore, and the like.

As the xanthene chromophore, chromophores represented by the following formulas (3-1) and (3-2) are preferred.

In the formula (3-1)

R ³¹ to R ³⁴ independently represent a hydrogen atom, -R ⁵⁶ or an aromatic hydrocarbon group having 6 to 10 carbon atoms (provided that the hydrogen atom contained in the aromatic hydrocarbon group is a halogen atom, -R ⁵⁶ , -OH, -OR ⁵⁶ , It is substituted with _{^{a, -CO 2 R 56, -SO 3}} R 56, -SO 2 NHR 57 or _{^{-SO 2 NR 57 R 58 - -SO}} 3 H, -SO 3 M, -SO 3 -, -COOH, -COO Lt; / RTI >

R ³⁵ to R ⁴⁰ independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms;

R ⁴¹ to R ⁴⁵ independently represent -SO ₃ H, -SO ₃ M, -SO ₃ ^- , -COOH, -CO ₂ R ⁵⁶ , -SO ₃ R ⁵⁶ , -SO ₂ NHR ⁵⁷ or -SO ₂ NR ⁵⁷ R ⁵⁸ ;

R ⁵⁶ represents a saturated hydrocarbon group having 1 to 10 carbon atoms (provided that the hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom, and the methylene group included in the saturated hydrocarbon group may be replaced with an oxygen atom, a carbonyl group, or -NR ⁵⁶ - Lt; / RTI >

R ⁵⁷ and R ⁵⁸ independently represent a straight chain alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms or -Z, or a substituent having 1 to 10 carbon atoms formed by bonding R ⁵⁷ and R ⁵⁸ together Or an unsubstituted heterocyclic group, provided that the hydrogen atom contained in the alkyl group and the cycloalkyl group may be substituted with a hydroxyl group, a halogen atom, -Z, -CH = CH ₂ or -CH = CHR ⁵⁶ , The methylene group contained in the alkyl group and the cycloalkyl group may be substituted with an oxygen atom, a carbonyl group or -NR ⁵⁶ -, and the hydrogen atom contained in the heterocyclic group may be substituted with -R ⁵⁶ , -OH or -Z;

M represents a sodium atom or a potassium atom;

Z represents an aromatic hydrocarbon group having 6 to 10 carbon atoms or an aromatic heterocyclic group having 5 to 10 carbon atoms (the hydrogen atoms contained in the aromatic hydrocarbon group and the aromatic heterocyclic group are -OH, R ⁵⁶ , -OR ⁵⁶ , -NO ₂ , -CH = CH ₂ , -CH = CHR ^56, or a halogen atom);

However, R ³¹ to R ³⁴ is at least one -COO ^- or -SO ₃ ^-, or aromatic hydrocarbon group having, or R ⁴¹ to R ⁴⁵ is at least one of -SO ₃ ^- Im]

In the formula (3-2)

R ⁴⁶ to R ⁵¹ independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a halogen atom;

R ⁵² to R ⁵⁵ is independently _{-OH, -SO 3 H, -SO 3} M, -SO 3 to each other ^{-, -COOH, -COO -, -CO} 2 R 56, -SO 3 R 56, -SO 2 NHR ⁵⁷ or -SO ₂ represents NR ⁵⁷ R ^58;

^{M, R 56, R 57,} R 58 is Im] ^{M, R 56, R 57,} R 58 and each agreement in the general formula (3-1)

The saturated hydrocarbon group at R ⁵⁶ may be any of linear, branched and cyclic, and may have a crosslinked structure when the number of carbon atoms is 1 to 10. Among them, the number of carbon atoms is preferably 1 to 8, more preferably 1 to 6, , More preferably from 1 to 4 carbon atoms. Specific examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a butyl group, a tert-butyl group, an isobutyl group, an amyl group, a tert- An aliphatic hydrocarbon group such as an octyl group, an isooctyl group, a tert-octyl group, a 2-ethylhexyl group, a nonyl group, or a decanyl group; Alicyclic hydrocarbon groups such as cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl; And a saturated hydrocarbon group having a crosslinked structure such as a tricyclodecanyl group. Examples of the group in which a methylene group contained in a saturated hydrocarbon group is substituted with an oxygen atom include a methoxypropyl group, an ethoxypropyl group, a 2-ethylhexyloxypropyl group, and a methoxyhexyl group. Of these, aliphatic hydrocarbon groups of 1 to 10 carbon atoms and alicyclic hydrocarbon groups of 3 to 10 carbon atoms are preferable, aliphatic hydrocarbon groups of 1 to 8 carbon atoms and alicyclic hydrocarbon groups of 5 to 8 carbon atoms are preferable, An aliphatic hydrocarbon group, a cyclopentyl group, and a cyclohexyl group are more preferable.

Examples of the substituted or unsubstituted heterocyclic group having 1 to 10 carbon atoms formed by bonding R ⁵⁷ and R ⁵⁸ to each other include pyrrole, pyridine, indole, isoindole, quinoline, isoquinoline, carbazole, phenanthridine, Phenothiazine, and the like. Examples of the substituent in the heterocyclic group include a halogen atom, a hydroxyl group, an alkoxy group, an amino group, and an alkyl group.

Examples of the aromatic heterocyclic group having 5 to 10 carbon atoms in Z include furyl, thienyl, pyridyl, pyrrolyl, oxazolyl, isoxazol, thiazolyl, isothiazolyl, A benzyl group, a benzyl group, a benzyl group, a benzyl group, and a benzyl group. Examples of the halogen atom include the same ones as described above.

Examples of the aromatic hydrocarbon group for R ³¹ to R ³⁴ and Z include a phenyl group and a naphthyl group.

Examples of -SO ₃ R ⁵⁶ in R ³¹ to R ³⁴ and R ⁴¹ to R ⁴⁵ include a methanesulfonyl group, an ethanesulfonyl group, a hexanesulfonyl group and a decanesulfonyl group. Examples of -CO ₂ R ⁵⁶ include a methyloxycarbonyl group, an ethyloxycarbonyl group, a propyloxycarbonyl group, an isopropyloxycarbonyl group, a butyloxycarbonyl group, a cyclohexyloxycarbonyl group, and a methoxypropyloxycarbonyl group. ^{_{Also, -SO 2 NHR 57, -SO 2}} NR 57 R R 57, R 58 of the ⁵⁸ examples of the alkyl group of the branched chain having 6 to 8, a cycloalkyl group having 5 to 7 carbon atoms, an allyl group, an aralkyl of having 8 to 10 An alkyl group, a hydroxyl group-containing alkyl group having 2 to 8 carbon atoms, an alkoxy group-containing alkyl group having 2 to 8 carbon atoms, and an aryl group.

Specific examples of the alkyl group in R ³⁵ to R ⁴⁰ and the alkyl group and halogen atom in R ⁴⁶ to R ⁵¹ include the same ones as described above.

Among the xanthan-based chromophores represented by the formulas (3-1) and (3-2), the following are preferable. That is, in the formula (3-1), a chromophore in which R ³¹ to R ³⁴ are an ethyl group, R ⁴¹ and R ⁴³ are -SO ₃ ^- , R ³⁵ to R ⁴⁰ , R ⁴² and R ⁴⁴ to R ⁴⁵ are hydrogen atoms desirable.

In the formula (3-2)

A chromophore wherein R ⁴⁶ and R ⁴⁹ are a bromine atom, R ⁴⁷ to R ⁴⁸ , and R ⁵⁰ to R ⁵⁵ are hydrogen atoms;

R ⁴⁶ , R ⁴⁷ , R ⁴⁹ and R ⁵¹ are bromine atoms, R ⁴⁸ , R ⁵⁰ and R ⁵² to R ⁵⁵ are hydrogen atoms;

R ⁴⁶ , R ⁴⁷ , R ⁴⁹ and R ⁵¹ are bromine atoms, R ⁵² to R ⁵⁵ are chlorine atoms, R ⁴⁸ and R ⁵⁰ are hydrogen atoms;

R ⁴⁶ , R ⁴⁷ , R ⁴⁹ and R ⁵¹ are iodine atoms, R ⁴⁸ , R ⁵⁰ and R ⁵² to R ⁵⁵ are hydrogen atoms;

R ⁴⁶ , R ⁴⁷ , R ⁴⁹ and R ⁵¹ are iodine atoms, R ⁵² to R ⁵⁵ are chlorine atoms, and R ⁴⁸ and R ⁵⁰ are hydrogen atoms.

As the triarylmethane chromophore, a chromophore represented by the following formula (4) is preferable.

[In the formula (4)

Ar represents a group represented by any one of the following formulas (4-a) and (4-b);

R ⁷¹ to R ⁷⁴ independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a phenyl group or a group having an ethylenically unsaturated bond;

R ⁷⁵ to R ⁸² independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, -COOR '(R' represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms) or a halogen atom]

[In the formula (4-a)

R ⁸³ to R ⁸⁷ independently represent hydrogen atom, -OH, -COOH, -COO ^- represents a ^{_{-, -SO 3 H, -SO 3}} M (M is a sodium atom or a potassium atom) or -SO _3;

* Denotes the combined hand,

However R ⁸³ to R ^87, at least one of which is -COO ^- or -SO ₃ ^- Im]

[In the formula (4-b)

R ⁸⁸ to R ⁹⁴ are each independently a hydrogen atom, -OH, -COOH, -COO ^- represents a ^{_{-, -SO 3 H, -SO 3}} M (M is a sodium atom or a potassium atom) or -SO _3;

* Denotes the combined hand,

At least one stage R ⁸⁸ to R ⁹⁴ is -COO ^- or -SO ₃ ^- Im]

Examples of the alkyl group having 1 to 8 carbon atoms and the cycloalkyl group having 3 to 8 carbon atoms according to R ⁷¹ to R ⁷⁴ include the same ones as described above.

In the group having an ethylenically unsaturated bond, the bonding position and the number of bonds of the ethylenically unsaturated bond are not particularly limited. Examples of the ethylenic unsaturated bond include a (meth) acryloyl group, a vinylaryl group, a vinyloxy group, and an allyl group. Among them, a (meth) acryloyl group is preferable in terms of ease of reaction. Preferable examples of the group having an ethylenically unsaturated bond include 2 - [(meth) acryloyloxy] ethyl group and the like.

Examples of the alkyl group having 1 to 8 carbon atoms (including R 'in -COOR' in R ⁷⁵ to R ⁸² ) according to R ⁷⁵ to R ⁸² include the same ones as described above. ^Examples of the halogen atom according to R ⁷⁵ to R ⁸² include the same ones as described above.

Among the triarylmethane chromophores represented by the formula (4), the following are preferable. R ⁸³ and R ⁸⁵ are -SO ₃ ^- , R ⁷¹ to R ⁷⁴ are an ethyl group, R ⁷⁵ to R ⁸² , R ⁸⁴ and R ⁸⁶ to R ⁸⁷ are groups represented by the formula (4-a) A chromophore which is a hydrogen atom is preferred.

As the azo-based chromophore, chromophores represented by the following formulas (5-1) and (5-2) are preferable.

[In the formula (5-1), "

R ¹⁰¹ represents a group represented by any one of the following formulas (5-a), (5-b) and (5-c);

R ¹⁰² to R ¹⁰⁶ are independently of each other hydrogen ^{atom, -R 121, -NR 122 R 123} , -NO 2, -OH, -COOH, -COO -, -SO 3 H, -SO 3 M (M is a sodium atom or a potassium atom) or -SO ₃ ^- represents;

R ¹²¹ represents an alkyl group having 1 to 6 (preferably 1 to 4) carbon atoms;

R ¹²² and R ¹²³ independently represent a hydrogen atom, a substituted or unsubstituted aryl group;

However, if R ¹⁰¹ is a group represented by the formula (5-a), at least one of R ¹⁰² to R ¹⁰⁶ is -COO ^- or -SO ₃ ^-, or, or -NR ¹²² R ^123, and R ¹²² and R ¹²³ of the an aryl group having, ^- at least one -COO ^- or -SO ₃

When R ¹⁰¹ is a group represented by the formula (5-b), R ¹⁰² to R ¹⁰⁶ and R ¹³⁷ to R ^142, at least one of which is -COO ^- or -SO ₃ ^-, or, or -NR ¹²² R ^123, and wherein R an aryl group having, ^at least one of R ¹²² and ¹²³ is -COO ^- or -SO ₃

R ^101, if the group represented by the formula (5-c), R ¹⁰² to R ¹⁰⁶ and R ¹⁴⁴ to at least one of R ¹⁵⁰ is -COO ^- or -SO ₃ ^-, or, or -NR ¹²² R ^123, and wherein R At least one of the -COO and ¹²² R ^{123 -} or -SO ₃ ^- aryl group having]

In the formula (5-2)

R ¹⁰⁷ through R ¹²⁰ independently represent hydrogen atom, -OH, -COOH, -COO ^- being ^{_{exhibited, -, -SO 3 H, -SO}} 3 M (M is a sodium atom or a potassium atom) or -SO ₃

However R ¹⁰⁷ to R ¹²⁰ is at least one -COO ^- or -SO ₃ ^- Im]

[In the formula (5-a)

R ¹³¹ to R ¹³⁶ independently represent a hydrogen atom or an alkyl group having 1 to 6 (preferably 1 to 4) carbon atoms;

* Indicates a combined hand)

In the formula (5-b)

R ¹³⁷ to R ¹⁴² are independently a hydrogen ^{atom, -NR 124 R 125, -OH,} -COOH, -COO each other _{^{-, -SO 3 H, -SO 3}} M (M is a sodium atom or a potassium atom) or -SO ₃ ^- ;

R ¹²⁴ and R ¹²⁵ independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms (preferably 1 to 4 carbon atoms), an alkylcarbonyl group or a cycloalkylcarbonyl group;

* Indicates a combined hand)

[In the formula (5-c)

R ¹⁴⁴ through R ¹⁵⁰ independently represent a hydrogen _{atom, -NO 2, -OH, -COOH,} -COO each other ^- a ^{_{-, -SO 3 H, -SO 3}} M (M is a sodium atom or a potassium atom) or -SO ₃ )

Examples of the alkyl group having 1 to 6 (preferably 1 to 4) carbon atoms in R ¹²¹ include the same groups as described above.

Examples of the aryl group in R ¹²² and R ¹²³ include an aryl group having 6 to 14 (preferably 6 to 10) carbon atoms, and specific examples thereof include a phenyl group, a naphthyl group, an anthryl group and a phenanthryl group , And a phenyl group are preferable. And the ^{like, wherein} the aryl group a may have, as the substituent -OH, -COOH, -COO substituent ^-, -SO ₃ H, -SO ₃ M (M is a sodium atom or a potassium atom) or -SO ₃ .

Examples of the alkyl group having 1 to 6 (preferably 1 to 4) carbon atoms in R ¹²⁴ and R ¹²⁵ include the same ones as described above.

The alkylcarbonyl in R ¹²⁴ and R ¹²⁵ is preferably an alkylcarbonyl group having 2 to 7 (preferably 2 to 4) carbon atoms, and specific examples thereof include a methylcarbonyl group, an ethylcarbonyl group, a propylcarbonyl group, a butylcarbonyl group, , Hexylcarbonyl group and the like. As the cycloalkylcarbonyl group, a cycloalkylcarbonyl group having 4 to 7 carbon atoms is preferable, and specifically, a cyclohexylcarbonyl group and the like can be given. Of these, a methylcarbonyl group and an ethylcarbonyl group are more preferable.

Examples of the alkyl group having 1 to 6 (preferably 1 to 4) carbon atoms in R ¹³¹ to R ¹³⁴ , R ¹³⁵ and R ¹³⁶ include the same ones as described above.

Of the azo type chromophore groups represented by the formulas (5-1) and (5-2), the following are preferable. That is, when R ¹⁰¹ in the formula (5-1) is a group represented by the formula (5-a)

R ¹⁰² is -COO ^-, R ¹³⁵ to R ¹³⁶ is a methyl group, R ¹⁰³ to R ¹⁰⁶ and R ¹³¹ to R ¹³⁴ is a hydrogen atom chromophore;

A chromophore in which R ¹⁰⁴ is -SO ₃ ^- , R ¹³⁵ to R ¹³⁶ are methyl groups, and R ¹⁰² to R ¹⁰³ , R ¹⁰⁵ to R ¹⁰⁶ , and R ¹³¹ to R ¹³⁴ are hydrogen atoms are preferable.

In the formula (5-1), when R ¹⁰¹ is a group represented by the formula (5-b)

R ¹⁰² to R ¹⁰⁶ are each a hydrogen atom, R ¹³⁷ and R ¹⁴⁰ are -SO ₃ ^- , R ¹⁴² is -NR ¹²⁴ R ¹²⁵ (R ¹²⁴ is a hydrogen atom, R ¹²⁵ is a methylcarbonyl group), R ¹³⁸ to R ¹³⁹ and R ^A chromophore in which ¹⁴¹ is a hydrogen atom;

R ¹⁰³ is -NR ¹²² R ^{123 wherein} R ¹²² is a hydrogen atom and R ¹²³ is a (p-sulfonic acid) phenyl group, R ¹⁰⁴ is a methyl group, R ¹³⁸ is -SO ₃ ^- , R ¹⁰² , R ¹⁰⁵ to R ¹⁰⁶ , R ¹³⁷ and R ¹³⁹ to R ¹⁴² are hydrogen atoms.

In the formula (5-1), when R ¹⁰¹ is a group represented by the formula (5-c)

A chromophore in which R ¹⁰⁴ is -SO ₃ ^- , R ¹⁴⁸ is -OH, R ¹⁰² to R ¹⁰³ , R ¹⁰⁵ to R ¹⁰⁶ , R ¹⁴⁴ to R ¹⁴⁷ , and R ¹⁴⁹ to R ¹⁵⁰ are hydrogen atoms;

A chromophore in which R ¹⁰⁴ is -SO ₃ ^- , R ¹⁵⁰ is -OH, R ¹⁰² to R ¹⁰³ , R ¹⁰⁵ to R ¹⁰⁶ , and R ¹⁴⁴ to R ¹⁴⁹ are hydrogen atoms are preferable.

In the formula (5-2)

A chromophore in which R ¹⁰⁸ , R ¹¹¹ , R ¹¹⁶ are -SO ₃ ^- , R ¹⁰⁷ is -OH, R ¹⁰⁹ to R ¹¹⁰ , R ¹¹² to R ¹¹⁵ , and R ¹¹⁷ to R ¹²⁰ are hydrogen atoms;

A chromophore in which R ¹¹¹ , R ¹¹³ and R ¹¹⁶ are -SO ₃ ^- , R ¹⁰⁷ is -OH, R ¹⁰⁸ to R ¹¹⁰ , R ¹¹² , R ¹¹⁴ to R ¹¹⁵ and R ¹¹⁷ to R ¹²⁰ are hydrogen atoms are preferable.

In the present invention, an azo-based chromophore represented by the following formula (5-3) may be applied.

[In the formula (5-3)

R ¹⁵¹ to R ¹⁵⁴ are independently a hydrogen atom, -OH, -COOH, -COO each other ^- being ^{_{exhibited, -, -SO 3 H, -SO}} 3 M (M is a sodium atom or a potassium atom) or -SO ₃

However R ¹⁵¹ to R ¹⁵⁴ is at least one -COO ^- or -SO ₃ ^- Im]

Among the azo-based chromophores represented by the formula (5-3), the following are preferable. That is, a chromophore in which R ¹⁵¹ and R ¹⁵⁴ are -SO ₃ ^- and R ¹⁵² to R ¹⁵³ are hydrogen atoms is preferred.

As the quinone-based chromophore, a chromophore represented by the following formula (6) is preferable.

In the formula (6)

R ¹⁷¹ through R ¹⁸⁰ independently represent a hydrogen ^{atom, -R 181, -OH, -COOH,} -COO each other _{^{-, -SO 3 H, -SO 3}} M (M is a sodium atom or a potassium atom), -SO ₃ ^- the are shown, with the proviso that R ¹⁷¹ to R ^180, at least one of which is -COO ^- or -SO ₃ ^-, and;

R ¹⁸¹ represents an alkyl group having 1 to 6 (preferably 1 to 4) carbon atoms]

As the alkyl group for R ¹⁸¹ , the same ones as mentioned above can be mentioned.

Of the quinone chromophores represented by the formula (6), the following are preferable. That is, a chromophore in which R ¹⁷¹ and R ¹⁷⁶ are -SO ₃ ^- , R ¹⁷³ and R ¹⁷⁸ are methyl groups, R ¹⁷² , R ¹⁷⁴ to R ¹⁷⁵ , R ¹⁷⁷ and R ¹⁷⁹ to R ¹⁸⁰ are hydrogen atoms are preferred.

As the phthalocyanine chromophore, a chromophore represented by the following formula (7) is preferable.

[In the formula (7)

R ²⁰¹ through R ²¹⁶ independently represent hydrogen atom, -OH, -COOH, -COO ^- being exhibited, with the proviso ^-, -SO ₃ H, -SO ₃ M (M is a sodium atom or a potassium atom) or -SO ₃ at least one of R ²⁰¹ to R ²¹⁶ is -COO ^- or -SO ₃ ^- Im]

Of the phthalocyanine chromophores represented by the formula (7), the following are preferable. That is, when R ²⁰² , R ²⁰⁶ , R ²¹⁰ and R ²¹⁴ are -SO ₃ ^- and R ²⁰¹ , R ²⁰³ to R ²⁰⁵ , R ²⁰⁷ to R ²⁰⁹ , R ²¹¹ to R ²¹³ and R ²¹⁵ to R ²¹⁶ are hydrogen atoms A chromophore is preferred.

As the acridine-based chromophore, a chromophore represented by the following formula (8) is preferable.

In the formula (8-1)

r8 represents an integer of 1 to 4;

R ²³¹ is a hydrogen atom, -OH, -COOH, -COO ^- if being exhibited, provided r8 is ^{_{1, -, -SO 3 H,}} -SO 3 M (M is a sodium atom or a potassium atom) or -SO ₃ R ²³¹ is -COO ^- or -SO ₃ ^-, and r8 is an integer of 2 to 4. in the case of at least one of the plurality of R ²³¹ is -COO ^- or -SO ₃ ^-, and the remaining R ²³¹ may be the same or different has exist〕

In the formula (8-2)

s8 represents an integer of 1 to 6;

For being exhibited, with the proviso that the s8 1, ^- R ²³² is a hydrogen ^{atom, -OH, -COOH, -COO -,} -SO 3 H, -SO 3 M (M is a sodium atom or a potassium atom) or -SO ₃ R ²³² is -COO ^- or -SO ₃ ^-, and s8 in the case of an integer from 2 to 6, at least one of the plurality of R ²³² is -COO ^- or -SO ₃ ^-, and the remaining R ²³² may be the same or different has exist〕

Of the acridine-based chromophores represented by the formulas (8-1) and (8-2), the following are preferable. In other words,

A chromophore in the formula (8-1) wherein r8 is 2 or 3 and a plurality of R ²³¹ are all -SO ₃ ^- ;

In the formula (8-2), a chromophore in which s8 is 2 and two R ²³² are all -SO ₃ ^- are preferable.

As the indigo-based chromophore, a chromophore represented by the following formula (9) is preferable.

[In the formula (9)

R ²⁵¹ through R ²⁵⁸ independently represent hydrogen atom, -OH, -COOH, -COO ^- being exhibited, with the proviso ^-, -SO ₃ H, -SO ₃ M (M is a sodium atom or a potassium atom) or -SO ₃ at least one of R ²⁵¹ to R ²⁵⁸ is -COO ^- or -SO ₃ ^- Im]

Of the indigo-based chromophores represented by the formula (9), the following are preferable. That is, a chromophore in which R ²⁵³ and R ²⁵⁷ are -SO ₃ ^- and R ²⁵¹ to R ²⁵² , R ²⁵⁴ to R ²⁵⁶ , and R ²⁵⁸ are hydrogen atoms is preferred.

Among the chromophores, a chroman-based chromophore having an anionic functional group, a triarylmethane chromophore having an anionic functional group, an azo chromophore having an anionic functional group, a quinone chromophore having an anionic functional group, a phthalocyanine chromophore having an anionic functional group , An acridine-based chromophore having an anionic functional group, and an indigo-based chromophore having an anionic functional group are preferable. Particularly, a chromanthan-based chromophore having an anionic functional group, an anionic functional group having an anionic functional group At least one chromophore selected from the group consisting of a triarylmethane chromophore having an anionic functional group and an indigo chromophore having an anionic functional group.

This colorant may be obtained, for example, by salt exchange reaction of a known acid dye with a known phosphonium salt compound.

As the known acidic dyes, there may be mentioned color indexes (C.I., published by The Society of Dyers and Colourists), C.I. A compound classified as an acid, for example, a dye having a color index (C.I.) name as shown below.

C.I. Acid Yellow 11, C.I. Acid Orange 7, C.I. Acid Red 37, C.I. Acid Red 180, C.I. Azo type acid dyes such as Acid Blue 29;

C.I. Acid Blue 1, C.I. Acid Blue 7, C.I. Acid Blue 9, C.I. Acid Blue 83, C.I. Acid Blue 90, C.I. Acid Blue 93, C.I. Triarylmethane-based acid dyes such as Acid Green 16;

C.I. Acid Blue 40, C.I. Anthraquinone-based acid dyes such as Acid Green 25;

C.I. Acid Red 52, C.I. Acid Red 87, C.I. Acid Red 92, C.I. Acid Red 289, C.I. Xanthene acid dyes such as Acid Red 388;

C.I. Quinoline-based acid dyes such as Acid Yellow 3;

C.I. Acid Yellow 1, C.I. Nitro-based acid dyes such as Acid Orange 3;

C.I. Quinone-based acid dyes such as Acid Green 25;

C.I. Phthalocyanine-based acid dyes such as Acid Blue 249;

C.I. Quinoline-based acid dyes such as Acid Yellow 3;

C.I. Acid Blue 59, C.I. Azine based acid dyes such as Acid Blue 102;

C.I. Acid Yellow 3, C.I. Acridine-based acid dyes such as Acid Yellow 5;

C.I. Acid dyes based on indigo such as Acid Blue 74.

Of these known acid dyes, xanthene dyes, triarylmethane dyes, azo dyes, quinone dyes, phthalocyanine dyes, acridine dyes and indigo dyes are preferable, and xanthene dyes, triarylmethane dyes, , Azo dyes and indigo dyes are more preferable.

As the known phosphonium salt compounds, there may be mentioned the compounds represented by the above-mentioned group of groups? To? With a halogen ion, a boron anion, a phosphate anion, a carboxylic acid anion, a sulfuric acid anion, an organic sulfonic acid anion, a nitrogen anion, a methide anion, And salts of at least one anion selected from the group consisting of ions. Among these, the compound group α to the cation shown in γ, fluoride ion, chloride ion, bromide ion, a halogen ion such as iodide ion, BF ₄ ^- inorganic boron anion, such _{as, (C 6 H 5) 4} B - A salt of at least one anion selected from the group consisting of an inorganic phosphate anion such as an organic boron anion PF ₆ ^- such as a sulfate anion, a nitrogen anion of [(CF ₃ SO ₂ ) ₂ N] ^- , and OH ^- It is preferable from the standpoint of availability.

The salt exchange reaction of the acid dye and the phosphonium salt compound can be carried out by a known method. For example, the known acid dye and the phosphonium salt compound are dissolved in a solvent and stirred to easily produce the present colorant can do. In this production, the solution may be heated if necessary.

The present colorant thus obtained can be used in various organic solvents such as (poly) alkylene glycol monoalkyl ethers such as propylene glycol monomethyl ether, (poly) alkylene glycol monoalkyl ether acetates such as propylene glycol monomethyl ether acetate And has excellent heat resistance and coloring power. Therefore, the present coloring agent is very useful as a coloring agent used in a coloring composition for a color filter and the like, and can be preferably used as an acidic coloring agent.

These colorants may be used alone or in combination of two or more.

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

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

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

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. Orange pigments such as Pigment Orange 38;

C.I. Pigment Violet 23 and other purple pigments.

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

In the present invention, when a pigment is used as another 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. Further, the pigment may be used by modifying its particle surface with a resin, if desired. As the resin for modifying the particle surface of the pigment, for example, a vehicle resin described in Japanese Patent Application Laid-Open No. 2001-108817 or a commercially available resin for dispersing various pigments may be mentioned. Examples of the resin coating method for the carbon black surface include a method described in Japanese Patent Application Laid-Open No. 9-71733, Japanese Patent Application Laid-Open No. 9-95625, Japanese Patent Application Laid-Open No. 9-124969 Can be adopted.

The organic pigment is preferably used by finely pulverizing primary particles by so-called salt milling. As a method of the salt milling, for example, a method disclosed in Japanese Unexamined Patent Application Publication No. 08-179111 can be adopted.

In the present invention, in the case of using a pigment as another colorant, further known dispersants and dispersion aids may be contained. Examples of the known dispersant include urethane-based dispersants, polyethyleneimine-based dispersants, polyoxyethylene alkyl ether-based dispersants, polyoxyethylene alkyl phenyl ether-based dispersants, polyethylene glycol diester dispersants, sorbitan fatty acid ester- A dispersant, and an acrylic dispersant, and as a dispersing aid, a pigment derivative and the like.

Disperbyk-2000, Disperbyk-2001, BYK-LPN6919, BYK-LPN21116 and BYK-LPN21324 (manufactured by BYK) are used as the acrylic dispersant. Disperbyk-161, Disperbyk-162, Disperbyk-165, Disperbyk-167, Disperbyk-170 and Disperbyk-182 (manufactured by BYK) (Manufactured by Lubrizol Corporation) as a polyethyleneimine-based dispersant and Agisper PB821, Ajisper PB822, Ajisper PB880 and Ajisper PB881 (manufactured by Ajinomoto Co., Ltd.) as polyester dispersants, Manufactured by Fine Techno Co., Ltd.), and the like.

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

The dyes other than the present colorant can be appropriately selected from various kinds of oil-soluble dyes, direct dyes, acid dyes, metal complex dyes and the like.

As the other colorant, an anion part constituting a chromophore and a colorant forming a salt of a cation other than a phosphonium cation may be used in combination. Examples of such a colorant include a salt-forming compound containing a xanthene acid dye and a quaternary ammonium salt compound, as described in Japanese Patent Laid-Open Publication No. 2011-138094, An anthraquinone-based acid dye and a quaternary ammonium salt compound.

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

In the present invention, when this coloring agent and another coloring agent are used in combination, the content of the present coloring agent is 10 to 80 mass%, preferably 15 to 70 mass%, and more preferably 20 to 60 mass% in the total coloring agent. Further, in the present invention, a mode in which the present colorant and a pigment are used in combination is preferable.

(A) the content of the coloring agent is usually from 5 to 70 mass%, preferably from 5 to 60 mass%, more preferably from 5 to 60 mass%, in the solid content of the coloring composition, from the viewpoint of forming a pixel having 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.

- (B) Binder Resin -

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

Examples of the unsaturated monomer (b1) include unsaturated monomers such as (meth) acrylic acid, maleic acid, maleic anhydride, succinic acid mono [2- (meth) acryloyloxyethyl], omega -carboxylic polycaprolactone mono , p-vinylbenzoic acid, and the like.

These unsaturated monomers (b1) may be used alone or in admixture of two or more.

As the unsaturated monomer (b2), for example,

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

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

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

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

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

These unsaturated monomers (b2) may be used alone or in admixture of two or more.

In the copolymer of the unsaturated monomer (b1) and the unsaturated monomer (b2), the copolymerization ratio of the unsaturated monomer (b1) in the copolymer is preferably 5 to 50 mass%, more preferably 10 to 40 mass%. By copolymerizing the unsaturated monomer (b1) 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 (b1) and the unsaturated monomer (b2), for example, JP-A-7-140654, JP-A-8-259876, Japanese Patent Laid-Open Nos. 10-31308, 10-300922, 11-174224, 11-258415, 2000-56118 And Japanese Patent Application Laid-Open No. 2004-101728.

Further, in the present invention, for example, Japanese Unexamined Patent Application Publication No. 5-19467, Japanese Unexamined Patent Application Publication No. 6-230212, Japanese Unexamined Patent Publication No. 7-207211, (Meth) acryloyl group and the like as a side chain, as disclosed in JP-A-09-325494, JP-A-11-140144 and JP-A-2008-181095 Containing polymer may be used as a binder resin. In the coloring composition of the present invention, a coloring composition having high sensitivity can be obtained by using a carboxyl group-containing polymer having a polymerizable unsaturated bond such as a (meth) acryloyl group in a side chain as a binder resin, .

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

The ratio (Mw / Mn) of the weight average molecular weight (Mw) to the number average molecular weight (Mn) of the binder resin in the present invention is preferably 1.0 to 5.0, more preferably 1.0 to 3.0. The term "Mn" as used herein refers to the number average molecular weight in terms of polystyrene measured by GPC (elution solvent: tetrahydrofuran).

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

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

In the present invention, the content of the binder resin is usually 10 to 1,000 parts by mass, preferably 20 to 500 parts by mass, per 100 parts by mass of the (A) colorant. If the content of the binder resin is too small, for example, the alkali developability may deteriorate or the storage stability of the obtained color composition may deteriorate. On the other hand, when the content is too large, the colorant concentration is relatively lowered. It may be difficult to achieve the color density.

- (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 which is 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 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, anhydrous glutaric acid, itaconic anhydride, phthalic anhydride and hexahydrophthalic anhydride, anhydrous pyromellitic acid, biphenyltetracarboxylic acid dianhydride , And 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 of ethylene oxide, 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 selected from the group consisting of pentaerythritol tetra (meth) acrylate, ethylene oxide and propylene oxide By Bell And dipentaerythritol hexa (meth) acrylate modified with at least one member selected from the group consisting of modified dipentaerythritol penta (meth) acrylate, ethylene oxide and propylene oxide.

Examples of the compound having two or more N-alkoxymethylamino groups include compounds having a melamine structure, a benzoguanamine structure, and a urea structure. Further, the melamine structure, benzoguanamine structure refers to a chemical structure having at least one triazine ring or phenyl-substituted triazine ring as a basic skeleton, and also includes 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) Tetra (alkoxymethyl) benzoguanamine, N, 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 trifunctional or higher aliphatic polyhydroxy compound with (meth) acrylic acid, (Meth) acrylate having a carboxyl group, N, N, N ', N', N '', N '' - hexa (alkoxymethyl) ) Benzoguanamine is preferred. Among the multifunctional (meth) acrylates obtained by reacting a trivalent or higher aliphatic polyhydroxy compound with (meth) acrylic acid, trimethylolpropane triacrylate, pentaerythritol triacrylate, dipentaerythritol pentaacrylate, di Among the polyfunctional (meth) acrylates having a carboxyl group, pentaerythritol hexaacrylate is a compound obtained by reacting pentaerythritol triacrylate with succinic anhydride, a compound obtained by reacting dipentaerythritol pentaacrylate with succinic anhydride Is particularly preferable in that the strength of the colored layer is high, the surface smoothness of the colored layer is excellent, and it is difficult to generate background contamination, film residue or the like 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 10 to 1,000 parts by mass, more preferably 20 to 500 parts by mass, per 100 parts by mass of the (A) colorant. In this case, if the content of the crosslinking agent is too small, there is a possibility that sufficient curability is not obtained. On the other hand, if the content of the crosslinking agent is too large, alkali developability is lowered when the alkali developing property is imparted to the coloring composition of the present invention, and background contamination, film residue or the like is generated on the substrate of the unexposed portion or on the light- It tends to be easy.

- Photopolymerization initiator -

The coloring composition of the present invention may contain a photopolymerization initiator. Thus, the coloring composition can be imparted with radiation sensitivity. The photopolymerization initiator used in the present invention is a compound that generates active species capable of initiating polymerization of (C) a crosslinking agent by exposure to radiation such as visible light, ultraviolet light, deep ultraviolet light, electron beam, or 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 compounds, polynuclear quinone compounds, diazo compounds, imidosulfonate compounds, onium salt compounds and the like.

In the present invention, the photopolymerization initiator may be used alone or in combination of two or more. As the photopolymerization initiator, 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 compound include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2-isopropylthioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, and the like.

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 nonimidazole-based compound is used as a photopolymerization initiator, it is preferable to use a hydrogen donor in combination because it can improve the sensitivity. The term "hydrogen donor" as used herein means a compound capable of donating a hydrogen atom to a radical generated from a nonimidazole-based compound by exposure. Examples of the hydrogen donor include mercaptan-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. However, it is preferable to use at least one kind of mercaptan-based hydrogen donor and at least one amine-carbonate donor in combination to improve the sensitivity .

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-based compound include 1,2-octanedione, 1- [4- (phenylthio) phenyl] -, 2- (O-benzoyloxime), ethanone, 1- [ (2-methylbenzoyl) -9H-carbazol-3-yl] -, 1- (O- -9H-carbazol-3-yl] -, 1- (O-acetyloxime), ethanone, 1- [ -Dimethyl-1,3-dioxolanyl) methoxybenzoyl} -9H-carbazol-3-yl] -, 1- (O-acetyloxime). As commercial products of O-acyloxime compounds, NCI-831 and NCI-930 (manufactured by Adeka Co., Ltd.) 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, 4-dimethylaminopropiophenone , Ethyl 4-dimethylaminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoate, 2,5-bis (4-diethylaminobenzal) cyclohexanone, 7-diethylamino- ) Coumarin, and 4- (diethylamino) chalcone.

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

-menstruum-

The coloring composition of the present invention contains the above components (A) to (C), and optionally other components, but usually is formulated as a liquid composition by blending a solvent. The solvent may be appropriately selected and used as long as the components (A) to (C) constituting the coloring composition and other components are dispersed or dissolved, and they do not react with these components and have appropriate volatility.

As such a solvent, for example,

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

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

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

Ketoalcohols such as diacetone alcohol;

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

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

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

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

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

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.

Of these solvents, propylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monoethyl ether acetate, and propylene glycol monomethyl ether acetate are preferable from the viewpoints of solubility, pigment dispersibility, Butylene glycol diacetate, 1,6-hexanediol, 1,6-hexanediol, 1,6-hexanediol, 1,6-hexanediol, 1,6-hexanediol, Diethyl acetate, ethyl lactate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, 3-methyl-3-methoxybutyl propionate, n-butyl acetate, Amyl formate, i-amyl acetate, n-butyl propionate, ethyl butyrate, i-propyl butyrate, n-butyl butyrate and ethyl pyruvate are preferable.

In the present invention, the solvents may be used alone or in admixture of two or more.

Although the content of the solvent is not particularly limited, the total amount of each component excluding the solvent of the coloring composition is preferably 5 to 50 mass%, more preferably 10 to 40 mass%. By such an embodiment, it is possible to obtain a colorant dispersion having good dispersibility and stability, and a colored composition having excellent coatability.

-additive-

The coloring composition of the present invention may contain various additives as required.

Examples of additives include thermal polymerization initiators such as azo compounds and organic peroxides; 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; A development improver such as succinic acid mono [2- (meth) acryloyloxyethyl] phthalate mono [2- (meth) acryloyloxyethyl], omega -carboxylic polycaprolactone mono (meth) acrylate; Siloxane oligomers having a reactive functional group disclosed in JP-A-2008-242078, and the like.

The coloring composition of the present invention can be prepared by an appropriate method. When the present coloring agent is a dye, for example, a method disclosed in JP-A-2008-58642, JP-A-2010-132874 . ≪ / RTI > When the present colorant is a dye and when it is used in combination with a pigment, as disclosed in JP-A-2010-132874, a dye solution containing the present colorant or the like is passed through a first filter, 1 filter is mixed with a separately prepared pigment dispersion or the like, and the resulting colored composition is passed through a second filter. Further, the dye containing the present coloring agent and the like, the components (B) to (C), and other components to be used as required are dissolved in a solvent, the obtained solution is passed through a first filter, A method may be employed in which the solution passed is mixed with a separately prepared pigment dispersion and the resulting colored composition is passed through a second filter. After passing the dye solution containing the present colorant and the like through the first filter, the dye solution which has passed through the first filter, and the components (B) to (C) A method may be employed in which the solution obtained is passed through a second filter and further a solution having passed through the second filter is mixed with a separately prepared pigment dispersion and the obtained color composition is passed through a third filter have.

Color filters and their fabrication Way

The color filter of the present invention comprises a colored layer containing the present colorant.

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 so as to partition a portion where a pixel is formed, if necessary. Next, a liquid composition of the blue radiation sensitive composition of the present invention containing, for example, the present coloring agent is applied onto the substrate, followed by prebaking to evaporate the solvent to form a coating film. Subsequently, this coating film is exposed through a photomask and then developed with an alkali developing solution 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 is used to apply, bake, 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 red pixels Arrays are sequentially formed on the same substrate. Thereby, a color filter in which pixel arrays of three primary colors of red, green, and blue are arranged on a substrate is obtained. However, in the present invention, the order of forming the pixels of each color is not limited to the above. In the first method for manufacturing a color filter, at least one of the pixel arrays of blue, green, and red may be a colored layer containing the acidic coloring agent of the present invention.

The black matrix can be formed by forming a metal thin film of chromium or the like formed by sputtering or vapor deposition into a desired pattern by using a photolithography method. Alternatively, the black matrix may be formed by using a radiation sensitive coloring composition in which a black coloring agent is dispersed, May be formed in the same manner as in the case of FIG. The coloring composition of the present invention can be suitably used for the formation of such a black matrix.

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

If desired, these substrates may be subjected to appropriate pretreatment such as chemical treatment with a silane coupling agent, plasma treatment, ion plating, sputtering, gas phase reaction, vacuum deposition, and the like.

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, Method and a slit die coating method are preferably employed.

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

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

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

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

Examples of the alkali developer 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 are preferable.

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

As the development processing method, a shower development method, a spray development method, a dip (immersion) development method, a puddle (liquid immersion) development method, or the like can be applied. The developing 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, from the viewpoint of the heat resistance of the present colorant.

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

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

Subsequently, a green pixel pattern and a red pixel pattern are successively formed on the same substrate using the respective green or red thermosetting coloring compositions as described above. Thus, 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. In the second method of manufacturing a color filter, at least one of the pixel arrays of blue, green, and red may be a colored layer containing the acidic coloring agent 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 the respective colors discharged into the compartments from being mixed. Therefore, the barrier rib is usually formed using a black radia radiation composition.

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

A protective film is formed on the thus-obtained pixel pattern as necessary, and then 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 preferably used for forming such a black spacer.

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

Display element

The display device 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 device having the color filter of the present invention may be of a transmissive type or a reflective type and may have a suitable structure. For example, a color filter is formed on a substrate separate from a driving substrate on which a thin film transistor (TFT) is disposed, and a substrate on which a driving substrate and a color filter are formed is opposed via a liquid crystal layer (Indium tin oxide) electrode or an IZO (mixture of indium oxide and zinc oxide) electrodes is formed on a substrate on which a color filter is formed on the surface of a driving substrate on which a thin film transistor A structure in which one substrate faces the liquid crystal layer is also possible. The latter structure can remarkably improve the aperture ratio and has an advantage that a bright and high-definition liquid crystal display element can be obtained.

In addition to a cold cathode fluorescent lamp (CCFL), a color liquid crystal display device having the color filter of the present invention may have a backlight unit using a white LED as a light source. 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, 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 and a white LED for obtaining a white light by mixing a blue LED and a YAG based phosphor; a combination of a blue LED and an orange light emitting phosphor and a green light emitting phosphor; A white LED for obtaining white light by mixing white light, an ultraviolet LED and a red LED, a white LED for obtaining a white light by mixing a green light emitting fluorescent substance and a blue light emitting fluorescent substance, and the like.

The color liquid crystal display device having the color filter of the present invention may be applied to a color liquid crystal display device such as a twisted nematic (TN) type, a super twisted nematic (STN) type, an in-plane switching (IPS) type, a vertical alignment (VA) type, an optically compensated birefringence ) Type liquid crystal mode can be applied.

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

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

<Examples>

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.

&Lt; Synthesis and evaluation of the present colorant &

1. Synthesis of the present colorant

Synthetic example One

To a 200 mL eggplant-shaped flask equipped with a stirrer was added a xanthene acidic dye C.I. 2.9 g (5.0 mmol) of Acid Red 52 and 29 mL of ion-exchanged water were added and heated to a bath temperature of 85 캜 in an oil bath with stirring. To this solution, a solution obtained by dissolving 5.2 g (10.26 mmol) of tributylhexadecylphosphonium bromide in 60 g of ion-exchanged water at room temperature was added little by little at the same temperature. It was confirmed that a water-insoluble colored oily substance was produced at the time when all of them were added. Thereafter, the mixture was stirred at the same temperature for 1 hour, and then cooled to an ambient temperature using an ice bath. The supernatant was removed by tilting and then the residue was washed with ion-exchanged water. The residue was dissolved in methanol, collected, and then concentrated under reduced pressure using a rotary evaporator. The obtained oil phase residue was dried under reduced pressure at 50 占 폚 for 12 hours to obtain 6.1 g of a red-purple solid.

^It was confirmed by the ¹ H-NMR spectrum (solvent: deuterated chloroform) that the obtained compound was a compound represented by the following formula (A-1). The obtained compound is referred to as a dye (A-1).

Synthetic example 2

A compound having a chromophore derived from Acid Red 52 and distearyldimethylammonium was synthesized according to the method described in paragraph [0131] of the specification of Japanese Patent No. 4492760. The obtained compound is referred to as a dye (A-2).

Synthetic example  3

In the same manner as in Synthesis Example 1 except that 3.38 g (5.00 mmol) of Acid Red 289 as a xanthene acid dye was used instead of Acid Red 52 in Synthesis Example 1, 6.34 g of a reddish purple solid was obtained. ^It was confirmed by the ¹ H-NMR spectrum (solvent: deuterated chloroform) that the obtained compound was a compound represented by the following formula (A-3). The obtained compound is referred to as a dye (A-3).

Synthetic example  4

In Synthesis Example 1, instead of Acid Red 52, 3.38 g (5.00 mmol) of Acid Red 289 as a xanthene acid dye and 3.53 g (10.26 mmol) of tributyl methylphosphonium iodide in place of tributylhexadecylphosphonium bromide ), The procedure of Synthesis Example 1 was repeated to obtain 3.20 g of a red-purple solid. ^It was confirmed by the ¹ H-NMR spectrum (solvent: deuterated chloroform) that the obtained compound was a compound represented by the following formula (A-4). The resulting compound is referred to as a dye (A-4).

Synthetic example  5

In the same manner as in Synthesis Example 1 except that 3.53 g (10.26 mmol) of tributylmethylphosphonium iodide was used in place of tributylhexadecylphosphonium bromide in Synthesis Example 1, 1.81 g of a red-purple solid was obtained. ^It was confirmed by the ¹ H-NMR spectrum (solvent: deuterated chloroform) that the obtained compound was a compound represented by the following formula (A-5). The resulting compound is referred to as a dye (A-5).

Synthetic example  6

In the same manner as in Synthesis Example 1 except for using 4.06 g (10.26 mmol) of tributyloctylphosphonium bromide instead of tributylhexadecylphosphonium bromide in Synthesis Example 1, 5.43 g of a red-purple solid was obtained. ^It was confirmed by the ¹ H-NMR spectrum (solvent: deuterated chloroform) that the obtained compound was a compound represented by the following formula (A-6). The obtained compound is referred to as a dye (A-6).

Synthetic example  7

Except that 3.38 g (5.00 mmol) of Acid Red 289 as a xanthene acid dye and 4.06 g (10.26 mmol) of tributyloctylphosphonium bromide instead of tributylphosphonium bromide were used in place of Acid Red 52 in Synthesis Example 1 In the same manner as in Synthesis Example 1, 5.96 g of a red-purple solid was obtained. ^It was confirmed by the ¹ H-NMR spectrum (solvent: deuterated chloroform) that the obtained compound was a compound represented by the following formula (A-7). The obtained compound is referred to as a dye (A-7).

Synthetic example  8

In the same manner as in Synthesis Example 1 except for using 4.63 g (10.26 mmol) of tributyldodecylphosphonium bromide instead of tributylhexadecylphosphonium bromide in Synthesis Example 1, 6.40 g of a red-purple solid was obtained. ^It was confirmed by the ¹ H-NMR spectrum (solvent: deuterated chloroform) that the obtained compound was a compound represented by the following formula (A-8). The obtained compound is referred to as a dye (A-8).

Synthetic example  9

In the same manner as in Synthesis Example 1 except that 3.99 g (10.26 mmol) of benzyltriphenylphosphonium chloride was used instead of tributylhexadecylphosphonium bromide in Synthesis Example 1, 5.93 g of a red-purple solid was obtained. ^It was confirmed by the ¹ H-NMR spectrum (solvent: deuterated chloroform) that the obtained compound was a compound represented by the following formula (A-9). The resulting compound is referred to as a dye (A-9).

Synthetic example  10

In the same manner as in Synthesis Example 1 except for using 5.19 g (10.26 mmol) of 4-butoxybenzyltriphenylphosphonium bromide instead of tributylhexadecylphosphonium bromide in Synthesis Example 1, 6.95 g of a red-purple solid was obtained . ^It was confirmed by the ¹ H-NMR spectrum (solvent: deuterated chloroform) that the obtained compound was a compound represented by the following formula (A-10). The obtained compound is referred to as a dye (A-10).

Synthetic example  11

In the same manner as in Synthesis Example 1 except for using 5.82 g (10.26 mmol) of n-hexadecyltriphenylphosphonium bromide instead of tributylhexadecylphosphonium bromide in Synthesis Example 1, 7.24 g of a reddish purple solid was obtained. ^It was confirmed by the ¹ H-NMR spectrum (solvent: deuterated chloroform) that the obtained compound was a compound represented by the following formula (A-11). The resulting compound is referred to as a dye (A-11).

Synthetic example  12

In the same manner as in Synthesis Example 1 except that 4.96 g (10.26 mmol) of n-decyltriphenylphosphonium bromide was used in place of tributylhexadecylphosphonium bromide in Synthesis Example 1, 6.84 g of a red-purple solid was obtained. ^It was confirmed by the ¹ H-NMR spectrum (solvent: deuterated chloroform) that the obtained compound was a compound represented by the following formula (A-12). The resulting compound is referred to as a dye (A-12).

Synthetic example  13

In the same manner as in Synthesis Example 1 except that 4.38 g (10.26 mmol) of n-hexyltriphenylphosphonium bromide was used instead of tributylhexadecylphosphonium bromide in Synthesis Example 1, 5.39 g of a reddish purple solid was obtained. ^It was confirmed by the ¹ H-NMR spectrum (solvent: deuterated chloroform) that the obtained compound was a compound represented by the following formula (A-13). The obtained compound is referred to as a dye (A-13).

Synthetic example  14

In the same manner as in Synthesis Example 1 except that 3.93 g (10.26 mmol) of allyltriphenylphosphonium bromide was used in place of tributylhexadecylphosphonium bromide in Synthesis Example 1, 5.94 g of a red-purple solid was obtained. ^It was confirmed by the ¹ H-NMR spectrum (solvent: deuterated chloroform) that the obtained compound was a compound represented by the following formula (A-14). The obtained compound is referred to as a dye (A-14).

Synthetic example  15

In the same manner as in Synthesis Example 1 except that 3.70 g (5.00 mmol) of tetramethylene bis (triphenylphosphonium) dibromide was used instead of tributylhexadecylphosphonium bromide in Synthesis Example 1, 5.73 g of a reddish purple solid . ^It was confirmed by the ¹ H-NMR spectrum (solvent: deuterated chloroform) that the obtained compound was a compound represented by the following formula (A-15). The obtained compound is referred to as a dye (A-15).

Synthetic example  16

6.49 g of a red-purple solid was obtained in the same manner as in Synthesis Example 1, except that 3.45 g (5.00 mmol) of Acid Blue 7, which is a triarylmethane acidic acid dye, was used instead of Acid Red 52 in Synthesis Example 1. [ ^It was confirmed by the ¹ H-NMR spectrum (solvent: deuterated chloroform) that the obtained compound was a compound represented by the following formula (A-16). The resulting compound is referred to as a dye (A-16).

Synthetic example  17

5.32 g of a dark blue solid was obtained in the same manner as in Synthesis Example 1, except that 2.83 g (5.00 mmol) of Acid Blue 1, which is a triarylmethane acidic acid dye, was used instead of Acid Red 52 in Synthesis Example 1. ^It was confirmed by the ¹ H-NMR spectrum (solvent: deuterated chloroform) that the obtained compound was a compound represented by the following formula (A-17). The resulting compound is referred to as a dye (A-17).

Synthetic example  18

7.67 g of a dark blue solid was obtained in the same manner as in Synthesis Example 1 except that 4.27 g (5.00 mmol) of Acid Blue 90, which is a triarylmethane acidic acid dye, was used instead of Acid Red 52 in Synthesis Example 1. [ ^It was confirmed by the ¹ H-NMR spectrum (solvent: deuterated chloroform) that the obtained compound was a compound represented by the following formula (A-18). The obtained compound is referred to as a dye (A-18).

Synthetic example  19

7.60 g of a dark blue solid was obtained in the same manner as in Synthesis Example 1 except that 4.13 g (5.00 mmol) of Acid Blue 83, which is a triarylmethane acidic acid dye, was used instead of Acid Red 52 in Synthesis Example 1. ^It was confirmed by the ¹ H-NMR spectrum (solvent: deuterated chloroform) that the obtained compound was a compound represented by the following formula (A-19). The obtained compound is referred to as a dye (A-19).

Synthetic example  20

5.34 g of a dark blue solid was obtained in the same manner as in Synthesis Example 1 except that 2.00 g (2.50 mmol) of Acid Blue 93, which is a triarylmethane acidic acid dye, was used instead of Acid Red 52 in Synthesis Example 1. [ ^It was confirmed by the ¹ H-NMR spectrum (solvent: deuterated chloroform) that the obtained compound was a compound represented by the following formula (A-20). The resulting compound is referred to as a dye (A-20).

Synthetic example  21

6.79 g of a dark green solid was obtained in the same manner as in Synthesis Example 1 except that 3.08 g (5.00 mmol) of Acid Green 16 as a triarylmethane acidic acid dye was used instead of Acid Red 52 in Synthesis Example 1. ^It was confirmed by the ¹ H-NMR spectrum (solvent: deuterated chloroform) that the obtained compound was a compound represented by the following formula (A-21). The obtained compound is referred to as a dye (A-21).

Synthetic example  22

4.65 g of a dark blue solid was obtained in the same manner as in Synthesis Example 1 except that 1.17 g (2.50 mmol) of Acid Blue 74, which is an indigo-based acid dye, was used instead of Acid Red 52 in Synthesis Example 1. ^It was confirmed by the ¹ H-NMR spectrum (solvent: deuterated chloroform) that the obtained compound was a compound represented by the following formula (A-22). The obtained compound is referred to as a dye (A-22).

2. Evaluation of the present colorant

The dye (A-1) was weighed and propylene glycol monomethyl ether was added so that the dye concentration was 0.1% by mass, 1% by mass and 10% by mass. These samples were stirred for 1 hour at 25 DEG C using a mix rotor, and then their dissolved state was confirmed visually.

As a result, it was confirmed that the dye (A-1) was completely dissolved in 10 mass% of propylene glycol monomethyl ether.

In the same manner, the dye (A-2) to the dye (A-22), C.I. Acid Red 52, C.I. Acid Red 289, C.I. Acid Blue 7, C.I. Acid Blue 1, C.I. Acid Blue 90, C.I. Acid Blue 83, C.I. Acid Blue 93, C.I. Acid Green 16 and C.I. Acid Blue 74 was evaluated for solubility. As a result, the dye (A-2) to the dye (A-22) were completely dissolved in 10 mass% of the propylene glycol monomethyl ether. Acid Red 52, C.I. Acid Red 289, C.I. Acid Blue 7, C.I. Acid Blue 1, C.I. Acid Blue 90, C.I. Acid Blue 83, C.I. Acid Blue 93, C.I. Acid Green 16 and C.I. Acid Blue 74 did not dissolve even at a dye concentration of 0.1% by mass.

Further, the 5% mass reduction temperature of the dye (A-1) to the dye (A-22) based on simultaneous thermogravimetric and differential thermal analysis was 250 ° C or more. On the other hand, C.I. Acid Red 52, C.I. Acid Red 289, C.I. Acid Blue 7, C.I. Acid Blue 1, C.I. Acid Blue 90, C.I. Acid Blue 83, C.I. Acid Blue 93, C.I. Acid Green 16 and C.I. The 5% mass reduction temperature based on the simultaneous thermogravimetric and differential thermal analysis of Acid Blue 74 was less than 200 占 폚. 5% mass reduction The higher the temperature, the higher the heat resistance of the colorant.

&Lt; Production of Pigment Dispersion >

Production Example 1

As a colorant, C.I. 15 parts by mass of Pigment Violet 23, 12.5 parts by mass (solid content concentration of 40% by mass) of BYK-LPN21116 (BYK) as a dispersant, and 72.5 parts by mass of propylene glycol monomethyl ether acetate as a solvent, To prepare a pigment dispersion (a-1).

&Lt; Preparation of dye solution >

Production Example 2

10 parts by mass of the dye (A-1) and 90 parts by mass of propylene glycol monomethyl ether acetate were mixed to prepare a dye solution (A-1).

Production Example 3

10 parts by mass of the dye (A-2) and 90 parts by mass of propylene glycol monomethyl ether acetate were mixed to prepare a dye solution (A-2).

Production Examples 4 to 23

10 parts by mass of the dye (A-3) to the dye (A-22) and 90 parts by mass of propylene glycol monomethyl ether acetate were mixed to prepare a dye solution (A-3) to a dye solution (A-22).

&Lt; Synthesis of binder resin >

Synthesis Example 23

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

Synthesis Example 24

In a flask equipped with a cooling tube and a stirrer, 144 parts by mass of cyclohexanone was charged and replaced with nitrogen. 48 parts by mass of cyclohexanone, 28.8 parts by mass of methacrylic acid, 18 parts by mass of butyl methacrylate, 18 parts by mass of methyl methacrylate, 2-ethylhexyl EO-modified acrylate , 18 parts by mass of cyclohexyl methacrylate and 37.2 parts by mass of glycerol methacrylate, 48 parts by mass of cyclohexanone and 2 parts by mass of 2,2'-azobis (2 , 4-dimethylvaleronitrile) were added dropwise over a period of 2 hours, and the mixture was polymerized at this temperature for 1 hour. Thereafter, the temperature of the reaction solution was raised to 90 占 폚, and polymerization was further carried out for 1 hour. Next, this solution was cooled to room temperature, and cyclohexanone was added thereto so as to have a non-volatile content of 33 mass%, whereby a resin (B2 ') solution was obtained. The obtained resin (B2 ') had Mw = 10700, Mn = 5600 and Mw / Mn = 1.91.

The entire amount of the resin (B2 ') solution was added to a flask equipped with a cooling tube and a stirrer, the temperature of the solution was raised to 90 ° C, and 2-methacryloyloxyethyl isocyanate (manufactured by Showa Denko K.K. Lens MOI) (35 mol% based on the number of moles of glycerol methacrylate) and 0.36 part of 4-methoxyphenol was added dropwise over 15 minutes under air bubbling conditions, and the mixture was maintained at this temperature for 1.5 hours Addition reaction was carried out. Next, this solution was cooled to room temperature, and cyclohexanone was added thereto so as to have a non-volatile content of 36 mass%, thereby obtaining a binder resin solution. The binder resin thus obtained had Mw = 12800, Mn = 6000 and Mw / Mn = 2.13. This binder resin is referred to as &quot; binder resin (B2) &quot;.

&Lt; Preparation and evaluation of colored composition >

Example 1

, 13.5 parts by mass of the pigment dispersion (a-1), 7.2 parts by mass of the dye solution (A-1), 9.9 parts by mass of the binder resin (B1) solution as the binder resin, and M-402 (dipentaerythritol 15.4 parts by mass of a mixture of lithol hexaacrylate and dipentaerythritol pentaacrylate), 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one as a photopolymerization initiator , 0.1 part by mass of NCI-930 (manufactured by ADEKA CORPORATION), 0.2 part by mass of Megafac F-554 (manufactured by DIC Corporation) as a fluorine surfactant, and 0.1 part by mass of propylene glycol And monomethyl ether acetate were mixed to prepare a coloring composition (CR1) having a solid content concentration of 20 mass%.

The coloring composition (CR1) was coated on a glass substrate using a spin coater, and then prebaked on a hot plate at 80 DEG C for 10 minutes to form a coating film. The same operation was performed by changing the number of revolutions of the spin coater to form three coat films having different film thicknesses.

Subsequently, after cooling the substrates to room temperature, radiation containing wavelengths of 365 nm, 405 nm, and 436 nm was irradiated onto each coating film without passing through a photomask using a high-pressure mercury lamp at an exposure amount of 2,000 J / m ² . Thereafter, discharging the developing solution to the developing pressure 1 kgf / cm ² (nozzle diameter 1 mm) containing 0.04% by weight aqueous potassium hydroxide solution of 23 ℃ with respect to these substrates were subjected to a shower development for 90 seconds. Thereafter, this substrate was cleaned with ultra-pure water, air-dried, and further baked in a clean oven at 230 캜 for 30 minutes to form a cured film for evaluation.

Chromatic evaluation

The chromaticity coordinate values (x, y) and the magnetic pole value (Y) in the C light source, the 2-degree field of view, and the CIE colorimetric system were measured using the color analyzer (MCPD2000 manufactured by Otsuka Denshi Co., Ltd.) . Further, the film thickness of the obtained cured film was measured by using Alpha Step IQ manufactured by Claitencor (KLA-Tencor). From the measurement results, the chromaticity coordinate value x, the magnetic pole value Y and the film thickness at the chromaticity coordinate value y = 0.080 were determined. The evaluation results are shown in Table 1. The larger the stimulus value Y is, the higher the light transmittance (luminance) is, and the thinner the film thickness, the higher the coloring power of the coloring agent.

Comparative Example 1

A coloring composition was prepared in the same manner as in Example 1 except that the dye solution (A-2) was used instead of the dye solution (A-1). The obtained coloring composition was evaluated in the same manner as in Example 1. [ The evaluation results are shown in Table 1.

Examples 2 to 22

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

Claims (11)

(A) a colorant, (B) a binder resin, and (C) a crosslinking agent, wherein the colorant composition comprises (A) an acidic colorant having a phosphonium cation as a colorant,
Wherein the phosphonium cation is represented by any one of the following formulas (1) and (2)
Wherein the acidic colorant having the phosphonium cation is at least one chromophore selected from the group consisting of a xanthene chromophore having an anionic functional group, a triarylmethane chromophore having an anionic functional group, and an indigo chromophore having an anionic functional group Lt; / RTI &gt;
(B) the binder resin is characterized by comprising a copolymer of an ethylenically unsaturated monomer (b1) having at least one carboxyl group and another copolymerizable ethylenically unsaturated monomer (b2) containing N-substituted maleimide &Lt; / RTI &gt;

[In the formula (1)
R ¹ to R ⁴ independently represent a hydrogen atom or an organic group, provided that at least one of R ¹ to R ⁴ is an organic group and two of R ¹ to R ⁴ may be bonded to form a ring]

[In the formula (2)
R ⁵ to R ¹⁰ independently represent a hydrogen atom or an organic group, provided that two of R ⁵ to R ¹⁰ may be bonded to form a ring;
X represents a divalent linking group]. The coloring composition for a color filter according to claim 1, wherein the total number of carbon atoms of the organic group constituting R ¹ to R ⁴ is 5 to 50. The coloring composition for a color filter according to claim 1 or 2, wherein the content of the acidic colorant having the phosphonium cation is 10 to 80 mass% of the total colorant. The coloring composition for a color filter according to claim 1 or 2, wherein the organic group is a hydrocarbon group. The coloring composition for a color filter according to claim 1 or 2, wherein the organic group is an aliphatic hydrocarbon group. The coloring composition for a color filter according to claim 1 or 2, wherein the binder resin (B) comprises a carboxyl group-containing polymer having a polymerizable unsaturated bond in a side chain. A color filter comprising a colored layer containing an acidic colorant having a phosphonium cation,
Wherein the phosphonium cation is represented by any one of the following formulas (1) and (2)
Wherein the acidic colorant having the phosphonium cation is at least one chromophore selected from the group consisting of a xanthene chromophore having an anionic functional group, a triarylmethane chromophore having an anionic functional group, and an indigo chromophore having an anionic functional group . &Lt; / RTI &gt;

[In the formula (1)
R ¹ to R ⁴ independently represent a hydrogen atom or an organic group, provided that at least one of R ¹ to R ⁴ is an organic group and two of R ¹ to R ⁴ may be bonded to form a ring]

[In the formula (2)
R ⁵ to R ¹⁰ independently represent a hydrogen atom or an organic group, provided that two of R ⁵ to R ¹⁰ may be bonded to form a ring;
X represents a divalent linking group]. A display device comprising the color filter according to claim 7. An acidic colorant comprising an anionic moiety and a phosphonium cation,
Wherein the anion portion is a chromophore selected from the group consisting of a xanthene chromophore having an anionic functional group, a triarylmethane chromophore having an anionic functional group, and an indigo chromophore having an anionic functional group,
Wherein the phosphonium cation is represented by any one of the following Chemical Formulas (1) and (2).

[In the formula (1)
R ¹ to R ⁴ independently represent a hydrogen atom or an organic group, provided that at least one of R ¹ to R ⁴ is an organic group and two of R ¹ to R ⁴ may be bonded to form a ring]

[In the formula (2)
R ⁵ to R ¹⁰ independently represent a hydrogen atom or an organic group, provided that two of R ⁵ to R ¹⁰ may be bonded to form a ring;
X represents a divalent linking group]. delete delete