TW201344361A - Colored photosensitive resin composition - Google Patents

Abstract

The present invention provides a colored photosensitive resin composition comprising a colorant, a resin, a polymerization compound, a polymerization initiator and a solvent; wherein the colorant comprises C.I. pigment green 58 and at least one selected from the group consisting of a yellow pigment, a blue pigment, a red pigment, a violet pigment and an orange pigment, and the percentage of the colorant is 20 % by mass or more and 50% by mass or less relative to the total amount of the solid content.

Description

Colored photosensitive resin composition

The present invention relates to a colored photosensitive resin composition.

The colored photosensitive resin composition is used for producing a color filter used for a display device such as a liquid crystal display panel, an electroluminescence panel, or a plasma display panel. In the case of such a colored photosensitive resin composition, a composition is known which contains CI Pigment Green 58 and CI Pigment Yellow 138 and CI Pigment Red 177 as a colorant, and the content of the colorant is relative to the coloring photosensitivity. The solid content of the resin composition was 14% by mass. (JP2011-118051-A).

When the coloring photosensitive resin composition known in the prior art is formed into a colored patterned coating film by a photolithography method, the unexposed portion may not be sufficiently removed by development, and a residue may be generated or a residual film may be formed.

The present invention contains the following invention.

[1] A colored photosensitive resin composition comprising a colorant, a resin, a polymerizable compound, a polymerization initiator, and a solvent, the colorant comprising CI Pigment Green 58, from a yellow pigment, a blue pigment, a red pigment, a purple pigment And at least one selected from the group consisting of orange pigments, The content of the colorant is 20% by mass or more and 50% by mass or less based on the total amount of the solid content.

[2] The colored photosensitive resin composition according to [1], wherein the resin is an addition polymer having a structural unit of at least one selected from the group consisting of a source of a free unsaturated carboxylic acid and an unsaturated carboxylic anhydride; .

[3] The colored photosensitive resin composition according to [1] or [2] wherein the ratio of the content of the resin to the content of the polymerizable compound is from 20:80 to 80:20 on a mass basis.

[4] A color filter formed of the colored photosensitive resin composition according to any one of [1] to [3].

[5] A display device comprising the color filter according to [4].

According to the colored photosensitive resin composition of the present invention, excellent developability is obtained when the colored patterned coating film is formed by the photolithography method.

The colored photosensitive resin composition of the present invention contains a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), and a solvent (E).

The colored photosensitive resin composition of the present invention is selected from the group consisting of a thiol compound (T), a leveling agent (F) and a adhesion promoter (G). One less is ideal.

The colored photosensitive resin composition of the present invention may further contain a polymerization initiation aid (D1).

<Colorant (A)>

The coloring agent (A) contains at least one selected from the group consisting of yellow pigment, blue pigment, red pigment, purple pigment and orange pigment, and C.I. Pigment Green 58, The content of the colorant is 20% by mass or more and 50% by mass or less, and preferably 25 to 45% by mass based on the total amount of the solid content. In the present specification, the "total amount of solid content" means the amount of the solvent (E) removed from the total amount of the colored photosensitive resin composition of the present invention.

As the yellow pigment, for example, CI Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117 can be cited. , 125, 128, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 194, 214, etc., ideally CI Pigment Yellow 138,150.

As the blue pigment, for example, C.I. Pigment Blue 15, 15:3, 15:4, 15:6, 60, 80 and the like can be cited.

As the red pigment, for example, CI Pigment Red 9,97,105,122,123,144,149,166,168,175,176,177,180,192,209,215,216,224,242 , 254, 255, 264, 265, etc., ideally CI Pigment Red 177.

As the purple raw material, for example, C.I. Pigment Violet 1, 19, 23, 29, 32, 36, 38, etc., and C.I. Pigment Violet 23 are preferable.

As the orange pigment, for example, CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and the like are exemplified, and CI Pigment Orange 38 is desirable. .

These pigments may be subjected to a rosin treatment as needed, a surface treatment such as a pigment derivative into which an acidic group or a basic group is introduced, a graft treatment of a pigment surface by a polymer compound or the like, and a micronization treatment such as a sulfuric acid micronization method. Or a treatment for removing an impurity, washing with an organic solvent or water, or the like, and removing the ionic impurities by an ion exchange method or the like. The particle size of the pigment is preferably uniform for each.

These pigments can be a pigment dispersion liquid in a state in which the pigment dispersant is uniformly dispersed in the pigment dispersant solution by containing a pigment dispersant and performing a dispersion treatment. The pigments may be separately dispersed and treated separately, or a plurality of kinds may be mixed and dispersed.

Examples of the pigment dispersant include a cationic dispersant, an anionic, a nonionic, an amphoteric, a polyester-based, a polyamine-based, and an acrylic-based pigment dispersant. These pigment dispersants may be used singly or in combination of two or more. The pigment dispersing agent is exemplified by trade name KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Flowlen (manufactured by Kyoei Chemical Co., Ltd.), Solsperse (manufactured by Zeneca Co., Ltd.), and EFKA (manufactured by CIBA Co., Ltd.). Ajisper (Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (manufactured by BYK Chemie Co., Ltd.), and the like.

When the pigment dispersant is used, the amount thereof is preferably 100 parts by mass or less, more preferably 5 parts by mass or more and 50 parts by mass or less based on 100 parts by mass of the pigment. When the amount of the pigment dispersant used is in the above range, there is a tendency that a pigment dispersion liquid in a uniformly dispersed state can be obtained.

The content of C.I. Pigment Green 58 is preferably from 20 to 99% by mass, more preferably from 30 to 95% by mass, based on the total amount of the colorant (A).

The content of the yellow raw material is preferably from 0.1 to 80% by mass, more preferably from 15 to 60% by mass, based on the total amount of the colorant (A).

The content of at least one selected from the group consisting of a blue pigment, a red pigment, a purple pigment, and an orange pigment is preferably 0.1 to 5% by mass, and 0.1 to 3 by mass based on the total amount of the colorant (A). % is more ideal.

<Resin (B)>

The resin (B) is not particularly limited, but an alkali-soluble resin is preferred, and an addition polymer having at least one structural unit selected from the group consisting of a source of a free unsaturated carboxylic acid and an unsaturated carboxylic anhydride is more preferable. . Examples of such a resin include the following resins [K1] to [K6].

The resin [K1] is at least one selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides (a) (hereinafter sometimes referred to as "(a)"), and a cyclic ether having 2 to 4 carbon atoms. a copolymer of a structure and an ethylenically unsaturatedly bonded monomer (b) (hereinafter sometimes referred to as "(b)"); a tree means [K2] (a) and (b), and may be shared with (a) Polymerized monomer (c) (however, it is different from (a) and (b).) (hereinafter sometimes referred to as "(c)") copolymer; resin [K3] (a) and (c) Copolymer; resin [K4] a copolymer of (a) and (c) with (b) a resin; a resin [K5] a copolymer of (b) and (c) with (a) a resin; [K6] A resin obtained by reacting the copolymer of (b) with (c) with (a) and then with a carboxylic anhydride.

In terms of (a), specifically, for example, acrylic acid can be cited. Unsaturated monocarboxylic acids such as methacrylic acid, 2-butenoic acid, o-, m-, p-ethylene benzoic acid; maleic acid, fumaric acid, citraconic acid, mesaconic acid ), itaconic acid, 3-vinyl phthalic acid, 4-vinyl phthalic acid, 3,4,5,6-tetrahydrofurfuric acid, 1,2,3,6-tetrahydrofurfuric acid, dimethyl An unsaturated dicarboxylic acid such as tetrahydrofurfuric acid or 1,4-cyclohexene dicarboxylic acid; methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]g 2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-B Bicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-ethylbicyclo[2.2.1]hept-2 - a bicyclic unsaturated compound containing a carboxyl group such as an alkene; maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1 , 2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydrate, etc., unsaturated dicarboxylic acid anhydride; succinic acid [2-(Methyl)acryloxyethyl), decanoic acid [2-(methyl) propylene oxy ethoxylate An unsaturated mono[(meth)acryloxyalkylalkyl] ester of a divalent or higher polyvalent carboxylic acid; an unsaturated group containing a hydroxyl group and a carboxyl group in the same molecule as α-(hydroxymethyl)acrylic acid Acrylates, etc.

Among these, acrylic acid, methacrylic acid, and maleic anhydride are preferable from the viewpoint of copolymerization reactivity and the solubility of the obtained resin in an aqueous alkali solution.

(b), for example, means a cyclic ether having a carbon number of 2 to 4. A structure (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and a polymerizable compound bonded to an ethylenic unsaturated group. (b) It is preferred to use a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloxy group.

In the present specification, "(meth)acrylic acid" means at least one selected from the group consisting of acrylic acid and methacrylic acid. The expressions of "(meth)acrylonitrile" and "(meth)acrylate" have the same meaning.

(b), for example, a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)"), having propylene oxide Oxetanyl and ethylenically unsaturated bonded monomer (b2) (hereinafter sometimes referred to as "(b2)"), a tetrahydrofuranyl group and an ethylenically unsaturated bonded monomer (b3) (hereinafter sometimes It is called "(b3)").

(b1), for example, a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "(b1-1)" The monomer (b1-2) having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "(b1-2)").

Examples of (b1-1) include glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, and β-B (meth)acrylate. Glycidylpropyl ester, epoxypropyl vinyl ether, o-vinylbenzyl epoxypropyl ether, m-vinylbenzyl epoxypropyl ether, p-vinylbenzyl epoxypropyl ether, α-Methyl-o-vinylbenzyl epoxypropyl ether, α-methyl-m-vinylbenzyl epoxypropyl ether, α-methyl-p-vinylbenzyl epoxypropyl ether , 2,3-bis(glycidoxymethyl)styrene, 2,4-bis(glycidoxymethyl)styrene, 2,5-bis(epoxypropyloxymethyl) Styrene, 2,6-bis(glycidoxymethyl)styrene, 2,3,4-tris(epoxypropyloxymethyl)styrene, 2,3,5-three (glyoxypropyloxymethyl)styrene, 2,3,6-tris(epoxypropyloxymethyl)styrene, 3,4,5-tris(epoxypropyloxymethyl) Styrene, 2,4,6-tris(epoxypropyloxymethyl)styrene, and the like.

(b1-2), vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celoxide 2000; manufactured by Daicel Co., Ltd.), (methyl) 3,4-Epoxycyclohexylmethyl acrylate (for example, Cyclomer A400; manufactured by Daicel), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer M100; Daicel ( The compound represented by the formula (I), the compound represented by the formula (II), and the like.

[In the formulae (I) and (II), R ^a and R ^b represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and a hydrogen atom contained in the alkyl group may be substituted with a hydroxyl group.

X ^a and X ^b represents a single bond ^{junction, -R c -, * - R} c -O -, * - R c -S- or * -R ^c -NH-.

R ^c represents an alkanediyl group having 1 to 6 carbon atoms.

* indicates the bond key with O].

Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a secondary butyl group, a tertiary butyl group and the like.

Examples of the alkyl group in which a hydrogen atom is substituted with a hydroxyl group include a methylol group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, and a 1-hydroxypropyl group. hydroxyl 1-methylethyl, 2-hydroxy-1-methylethyl, 1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl, 4-hydroxybutyl and the like.

The R ^a and R ^b are preferably a hydrogen atom, a methyl group, a methylol group, a 1-hydroxyethyl group or a 2-hydroxyethyl group, and more preferably a hydrogen atom or a methyl group.

Examples of the alkanediyl group include a methylene group, an ethyl group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, and a pentane-1 group. 5-diyl, hexane-1,6-diyl and the like.

The X ^a and X ^b are preferably a single bond, a methylene group, an ethyl group, a *-CH ₂ -O- group, and a *CH ₂ CH ₂ -O- group, and more preferably a single bond. *-CH ₂ CH ₂ -O- (* indicates a bond with O).

The compound represented by the formula (I) may, for example, be a compound represented by the formula (I-1) to the formula (I-15). Wherein, in particular, the formula (I-1), the formula (I-3), the formula (I-5), the formula (I-7), the formula (I-9) or the formula (I-11) to the formula (I- The compound represented by 15) is preferably a compound represented by the formula (I-1), the formula (I-7), the formula (I-9) or the formula (I-15).

The compound represented by the formula (II) may, for example, be a compound represented by any one of the formulae (II-1) to (II-15). Wherein, in particular, the formula (II-1), the formula (II-3), the formula (II-5), the formula (II-7), the formula (II-9) or the formula (II-11) to the formula (II- The compound represented by 15) is ideal, and the compound represented by the formula (II-1), the formula (II-7), the formula (II-9) or the formula (11-15) is more preferable.

The compound represented by the formula (I) and the compound represented by the formula (II) may be used singly or in combination with the compound represented by the formula (II). When these are used in combination, the content ratio of the compound represented by the formula (I) and the compound represented by the formula (II) is on a molar basis, preferably from 5:95 to 95:5, more preferably from 10:90 to 90:10. More ideally, it is 20:80 to 80:20.

In the case of (b2), a monomer having an oxypropylene group and a (meth)acryloxy group is more preferable. In the case of (b2), 3-methyl-3-methylpropenyloxymethyl propylene oxide, 3-methyl-3-propenyloxymethyl propylene oxide, 3-ethyl- 3-methylpropenyloxymethyl propylene oxide, 3-ethyl-3-propenyloxymethyl propylene oxide, 3-methyl-3-methylpropenyloxyethyl propylene oxide, 3-methyl-3-propenyloxyethyl propylene oxide, 3-ethyl-3-methylpropenyloxyethyl propylene oxide, 3-ethyl-3-propenyloxyethyl ring Oxypropane and the like.

For (b3), with tetrahydrofuranyl and (methyl) propyl The monomer of the oxiranyloxy group is more desirable. Specific examples of (b3) include tetrahydrofuran methyl acrylate (for example, Biscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofuran methyl methacrylate, and the like.

In the case of (b), (b1) is preferable from the viewpoint of further improving the heat resistance and chemical resistance of the obtained color filter. Further, from the viewpoint of excellent storage stability of the colored photosensitive resin composition, (b1-2) is more preferable.

(c), for example, methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, n-butyl (meth)acrylate, (methyl) Tertiary butyl acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, (meth)acrylic acid Cyclopentyl ester, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 ^2.6 ]decane-8-ester (in the technical field) The customary name is "dicyclopentanyl (meth) acrylate." Also, sometimes referred to as "tricyclodecyl (meth) acrylate), trimethyl [meth) acrylate [5.2.1.0 ^2.6 ] decene -8-ester (commonly known in the art as "dicyclopentenyl (meth)acrylate".), dicyclopentyloxyethyl (meth)acrylate, isodecyl (meth)acrylate , (cyclo) (meth) acrylate, allyl (meth) acrylate, propargyl (meth) acrylate, phenyl (meth) acrylate, naphthyl (meth) acrylate, (meth) acrylate (meth) acrylate such as benzyl ester; 2-hydroxy (meth) acrylate a hydroxy group-containing (meth) acrylate such as 2-hydroxypropyl (meth) acrylate; a dicarboxylic acid diester such as diethyl maleate, diethyl fumarate or diethyl itaconate. Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[ 2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5 -Methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene ,5,6-bis(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5, 6-Dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2. 1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tertiary butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1 Hept-2-ene, 5,6-bis(tertiary butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2. 2.1] Bicyclic unsaturated compounds such as hept-2-ene; N-phenyl maleimine, N-cyclohexylmaleimide, N-benzyl maleimide, 3-Malaysia Amine benzoic acid N-succinimide, 4-maleimide butyric acid N-succinimide, 6-maleimide caproic acid N-succinimide, 3-male N-succinimide, iminopropionate, dicarbonyl quinone imine derivatives such as N-(9-acridinyl)maleimide; styrene, alpha -methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, propylene Guanidine, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, and the like.

Among these, from the viewpoints of copolymerization reactivity and heat resistance, styrene, vinyl toluene, benzyl (meth) acrylate, trimethyl [meth) acrylate [5.2.1.0 ^2.6 ] decane-8 - ester, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide and bicyclo [2.2.1]hept-2-ene are ideal.

In the resin [K1], the ratio derived from the respective structural unit is, in the entire structural unit constituting the resin [K1], the structural unit derived from (a): 2 to 60 mol%, derived from (b) The structural unit: 40 to 98 mol% is ideal, and the structural unit derived from (a): 10 to 50 mol% of the structural unit derived from (b): 50 to 90 mol% is more desirable.

When the ratio of the structural unit of the resin [K1] is in the above range, the storage stability of the colored photosensitive resin composition, the developability when the colored patterned coating film is formed, and the solvent resistance of the obtained color filter are Excellent tendency.

Resin [K1], for example, can refer to the method described in the "Experimental Method for Polymer Synthesis" (Dazu Takashi, Institute of Chemicals, 1st Edition, 1st, 1st, March 1, 1972) and the literature. Manufactured by the cited documents.

Specifically, a predetermined amount of (a) and (b), a polymerization initiator, a solvent, and the like are placed in a reaction container, and for example, by replacing oxygen with nitrogen to form a deoxidizing environment, heating is performed while stirring. The method of insulation. In this case, the polymerization initiator and the solvent used herein are not particularly limited, and a polymerization initiator and a solvent which are generally used in the art can be used. E.g, Examples of the polymerization initiator include an azo compound (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic The solvent (such as a benzamidine peroxide) may be a solvent (E) which will be described later as a solvent of the colored photosensitive resin composition of the present invention, as long as it can dissolve each monomer.

Further, the obtained copolymer may be used as it is, or a concentrated or diluted solution may be used, or a solid (powder) may be obtained by a method such as reprecipitation. In particular, by using a solvent contained in the colored photosensitive resin composition of the present invention as a solvent during polymerization, the solution after the reaction can be directly used for the preparation of the colored photosensitive resin composition of the present invention, and the present invention can be simplified. A manufacturing step of coloring the photosensitive resin composition.

In the resin [K2], the ratio derived from the respective structural unit is, in the entire structural unit constituting the resin [K2], the structural unit derived from (a): 2 to 45 mol% derived from (b) The structural unit: 2 to 95 mol% of the structural unit derived from (c): 1 to 65 mol% is ideal, and the structural unit derived from (a): 5 to 40 mol% derived from (b) Structural unit: 5 to 80 mol% of the structural unit derived from (c): 5 to 60% by mole is more desirable.

When the ratio of the structural unit of the resin [K2] is in the above range, the storage stability of the photosensitive resin composition is colored, and when the colored patterned coating film is formed The developability and the obtained color filter tend to have excellent solvent resistance, heat resistance and mechanical strength.

The resin [K2] can be produced in the same manner as the method described in the production method of the resin [K1], for example.

In the resin [K3], the ratio derived from the respective structural unit is, in the entire structural unit constituting the resin [K3], the structural unit derived from (a): 2 to 60 mol% derived from (c) The structural unit: 40 to 98 mol% is ideal, with the structural unit derived from (a): 10 to 50 mol% of the structural unit derived from (c): 50 to 90 mol% is more desirable. The resin [K3] can be produced in the same manner as the method described in the production method of the resin [K1], for example.

The resin [K4], after obtaining the copolymer of (a) and (c), (b) having a cyclic ether having 2 to 4 carbon atoms and (a) having a carboxylic acid and/or a carboxyl group Manufactured by addition of an acid anhydride.

First, the copolymer of (a) and (c) is produced in the same manner as the method described as the method for producing the resin [K1]. In this case, the ratio derived from the respective structural units is preferably the same as the ratio of those listed in the resin [K3].

Next, a part of the carboxylic acid and/or carboxylic anhydride derived from (a) in the copolymer is reacted with a cyclic ether having 2 to 4 carbon atoms which (b) has.

After the production of the copolymer of (a) and (c), the reaction environment of (b), carboxylic acid or carboxylic anhydride and cyclic ether is replaced by air in the atmosphere of the flask. A resin such as tris(dimethylaminomethyl)phenol or the like, and a polymerization inhibitor (for example, hydroquinone) may be placed in a flask, for example, at 60 to 130 ° C for 1 to 10 hours to produce a resin [K4]. .

The amount of use of (b) is preferably 5 to 80 moles per 100 moles, more preferably 10 to 75 moles. In this range, the storage stability of the colored photosensitive resin composition, the developability at the time of forming the patterned coating film, and the balance of solvent resistance, heat resistance, mechanical strength and sensitivity of the obtained patterned coating film are A tendency to become good. Since the reactivity of the cyclic ether is high and the unreacted (b) does not easily remain, the (b) for the resin [K4] is preferably (b1), and more preferably (b1-1).

The amount of the reaction catalyst to be used is preferably 0.001 to 5 parts by mass based on 100 parts by mass of the total of (a), (b) and (c). The amount of the polymerization inhibitor to be used is preferably 0.001 to 5 parts by mass based on 100 parts by mass of the total of (a), (b) and (c).

The reaction conditions such as the charging method, the reaction temperature, and the time can be appropriately adjusted in consideration of the production equipment and the calorific value due to polymerization. Further, similarly to the polymerization conditions, the charging method and the reaction temperature can be appropriately adjusted in consideration of the production equipment and the calorific value due to the polymerization.

Resin [K5], in the first stage, a copolymer of (b) and (c) was obtained in the same manner as in the above-described method for producing the resin [K1]. In the same manner as described above, the obtained copolymer may be used as it is, or a concentrated or diluted solution may be used, or a solid (powder) taken out by a method such as reprecipitation may be used.

The ratio of the structural units derived from (b) and (c) with respect to the constituents The total number of moles of the total structural unit of the polymer, respectively, from the structural unit derived from (b): 5 to 95 mol% of the structural unit derived from (c): 5 to 95 mol% is ideal, derived from The structural unit of (b): 10 to 90 mol% of the structural unit derived from (c): 10 to 90 mol% is more desirable.

Further, the cyclic ether derived from (b) and the carboxylic acid (a) possessed by the copolymer of (b) and (c) are the same conditions as in the method for producing the resin [K4]. The carboxylic anhydride is reacted to obtain a resin [K5].

The amount of (a) used in the reaction with the aforementioned copolymer is preferably 5 to 80 moles per 100 moles of (b). Since the reactivity of the cyclic ether is high and the unreacted (b) does not easily remain, the (b) for the resin [K5] is preferably (b1), more preferably (b1-1).

The resin [K6] is a resin which reacts the resin [K5] with a carboxylic acid anhydride.

The hydroxyl group produced by the reaction of a cyclic ether with a carboxylic acid or a carboxylic anhydride is reacted with a carboxylic acid anhydride.

As the carboxylic anhydride, there may be mentioned maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1, 2, 3 6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydrate, and the like. The amount of the carboxylic anhydride to be used is preferably from 0.5 to 1 mol per mol of the amount of (a).

Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth)acrylic acid (meth)acrylic acid copolymer and 3,4-epoxy (meth)acrylic acid. Resin such as bis-ring [5.2.1.0 ^2.6 ] decyl ester/(meth)acrylic acid copolymer [K1]; glycidyl (meth) acrylate / benzyl (meth) acrylate / (meth) acrylate copolymer , (meth)acrylic acid propylene acrylate / styrene / (meth) acrylic acid copolymer, (meth)acrylic acid 3,4-epoxytricyclo[5.2.1.0 ^2.6 ] decyl ester / (meth)acrylic acid /N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo(5.2.1.0 ^2.6 ]decyl (meth)acrylic/vinyltoluene copolymer (3-) (meth)acrylate, 3- Resin such as methyl-3-(meth)acryloxymethyl propylene oxide/(meth)acrylic acid/styrene copolymer [K2]; benzyl (meth)acrylate/(meth)acrylic acid copolymer , styrene/(meth)acrylic acid copolymer, benzyl (meth) acrylate / tricyclodecyl (meth) acrylate / (meth) acrylate copolymer [K3]; benzyl (meth) acrylate Ester/(meth)acrylic acid copolymer addition of (meth)acrylic acid propyl acrylate resin, (meth)acrylic acid Tricyclodecyl methacrylate / styrene / (meth) acrylate copolymer addition of (meth) acrylate propyl acrylate resin, trimethyl decyl (meth) acrylate / benzyl (meth) acrylate / (A a resin such as a resin obtained by adding an acrylic acid copolymer to a glycidyl (meth)acrylate [K4]; a copolymer of tricyclodecyl (meth)acrylate/glycidyl (meth)acrylate and a resin reactive with methyl methacrylate, a resin such as a resin obtained by reacting a copolymer of tricyclodecyl (meth) acrylate/styrene/glycidyl methacrylate with (meth)acrylic acid [K5]; A resin such as a resin obtained by reacting a copolymer of tricyclodecyl methacrylate/glycidyl methacrylate with (meth)acrylic acid and a resin which is reacted with tetrahydrophthalic anhydride, etc. [K6].

The resin (B) is preferably one selected from the group consisting of the resin [K1], the resin [K2] and the resin [K3], and more preferably the resin [K2] and One selected from the group formed by the resin [K3]. In the case of these resins, the colored photosensitive resin composition has excellent developability.

From the viewpoint of coloring the adhesion between the coating film and the substrate, the resin [K2] is more preferable.

The polystyrene-equivalent weight average molecular weight of the resin (B) is desirably 3,000 to 100,000, more desirably 5,000 to 50,000, still more preferably 5,000 to 30,000. When the molecular weight is in the above range, the hardness of the coating film is increased, the residual film ratio is also high, the solubility of the unexposed portion to the developer is good, and the resolution of the colored patterned coating film tends to be improved.

The molecular weight distribution [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (B) is desirably 1.1 to 6, more preferably 1.2 to 4.

The acid value of the resin (B) is desirably 50 to 170 mg-KOH/g, more desirably 60 to 150 mg-KOH/g, still more preferably 70 to 135 mg-KOH/g. The acid value here is a value measured by neutralizing the amount (mg) of potassium hydroxide required for 1 g of the resin (B), and can be obtained, for example, by titration with an aqueous potassium hydroxide solution.

The content of the resin (B) is desirably from 7 to 65 mass%, more desirably from 13 to 60 mass%, and still more preferably from 17 to 55 mass%, based on the total amount of the solid component. When the content of the resin (B) is within the above range, a colored patterned coating film can be formed, and the resolution and residual film ratio of the colored patterned coating film tend to be improved.

<Polymerizable compound (C)>

The polymerizable compound (C) is a compound which can be polymerized by an active radical and/or an acid generated from the polymerization initiator (D), and for example, it can be exemplified A compound of an ethylenically unsaturated bond or the like is preferably a (meth) acrylate compound.

Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such a polymerizable compound include trimethylolpropane tris(meth)acrylate, neopentyl glycol tri(meth)acrylate, and neopentyl glycol tetra(meth)acrylate. Dipentaerythritol penta(meth)acrylate, dineopentaerythritol hexa(meth)acrylate, tricrostitol octa(meth)acrylate, tricrostitol heptyl (meth)acrylate Ester, tetrapentaerythritol decamethacrylate, tetrapentaerythritol penta(meth)acrylate, tris(2-(methyl)propenyloxyethyl) isocyanurate, Ethylene glycol modified with neopentyl glycol tetra(meth)acrylate, ethylene glycol modified dipentaerythritol hexa(meth)acrylate, propylene glycol modified neopentyl glycol tetra(meth)acrylate, Propylene glycol modified dipentaerythritol hexa(meth)acrylate, caprolactone modified pentaerythritol tetrakis(meth)acrylate, caprolactone modified dipentaerythritol hexa(meth)acrylate Wait.

Among them, dipentaerythritol penta(meth)acrylate and dineopentaerythritol hexa(meth)acrylate are preferred.

The weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, more preferably 250 to 1,500 or less.

The content of the polymerizable compound (C) is preferably from 7 to 65% by mass, more preferably from 13 to 60% by mass, still more preferably from 17 to 55% by mass, based on the total amount of the solid content.

Further, the content ratio of the resin (B) to the polymerizable compound (C) [resin (B): polymerizable compound (C)] is preferably 20:80 to 80:20 on a mass basis, more preferably The ideal is 35:65 to 80:20, and more preferably 50:50 to 75:25, especially ideally 55:45 to 70:30.

When the content of the polymerizable compound (C) is within the above range, the residual film ratio at the time of forming the colored patterned coating film and the chemical resistance of the color filter tend to be improved.

<Polymerization initiator (D)>

The polymerization initiator (D) is not particularly limited as long as it can generate a living radical, an acid or the like by the action of light or heat, and a known polymerization initiator can be used.

As the polymerization initiator (D), an alkylphenone compound can be cited, three A compound, a mercaptophosphine oxide compound, an O-mercaptopurine compound, a biimidazole compound or the like.

The aforementioned O-indenyl ruthenium compound is a compound having a partial structure represented by the formula (d1). Hereinafter, * indicates a keying key.

With respect to the aforementioned O-indenyl ruthenium compound, for example, N-benzyl decyloxy-1-(4-phenylthiophenyl)butan-1-one-2-imine, N-benzyl Mercaptooxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, N-benzylidenyloxy-1-(4-phenylthiophenyl)- 3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzyl)-9H-indazole-3- Ethyl]imine-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxo Heterocyclic pentylmethyloxy)benzylhydrazinyl}-9H-indazol-3-yl]ethane-1-imine, N- Ethyloxy-1-[9-ethyl-6-(2-methylbenzyl)-9H-indazole)-3-yl]-3-cyclopentylpropane-1-imine, N- Benzyl methoxy-l-[9-ethyl-6-(2-methylbenzyl)-9H-indazol-3-yl]-3-cyclopentylpropan-1-one-2-a Amines, etc. Commercial products such as Irgacure OXE01, OXE02 (above, BASF Corporation, N-1919 (made by ADEKA)) can also be used.

Wherein, the O-indenyl hydrazine compound is derived from N-benzyl hydrazino oxy-1-(4-phenylthiophenyl)butan-1-one-2-imide, N-benzyl fluorenyloxy 1-(4-phenylthiophenyl)octane-1-one-2-imine and N-benzylhydrazinooxy-1-(4-phenylthiophenyl)-3-cyclopentyl At least one selected from the group consisting of propane-1.-keto-2-imine is preferred, N-benzylidenyloxy-1-(4-phenylthiophenyl)octane-1- Keto-2-imine is more desirable.

The phenylalkanone compound has a partial structure represented by the formula (d2) or a compound having a partial structure represented by the formula (d3). In some of these structures, the benzene ring may have a substituent.

With respect to the compound having a partial structure represented by the formula (d2), for example, 2-methyl-2-(N-morpholinyl)-1-(4-methylthiophenyl)propane-1- Ketone, 2-dimethylamino-1-(4-(N-morpholinyl)phenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[ (4-Methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one. Commercial products such as Irgacure 369, 907, and 379 (above, manufactured by BASF Corporation) can also be used.

In the case of a compound having a partial structure represented by the formula (d3), for example, Either 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-(4-(2-hydroxyethoxy)phenyl]propane-1- Oligomeric ketone, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxybenzene Ethyl ketone, benzyl dimethyl ketal, and the like.

From the viewpoint of sensitivity, a compound having a partial structure represented by the formula (d2) is preferred for the phenylalkanone compound.

The biimidazole compound is, for example, a compound represented by the formula (d5).

[In the formula (d5), R ³ to R ⁸ represent an aryl group having 6 to 10 carbon atoms which may have a substituent].

Examples of the aryl group having 6 to 10 carbon atoms include a phenyl group, a tolyl group, a xylyl group, an ethylphenyl group, a naphthyl group and the like, and a phenyl group is preferable.

Examples of the substituent include a halogen atom, an alkoxy group having 1 to 4 carbon atoms, and the like. The halogen atom may, for example, be a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, and is preferably a chlorine atom. Examples of the alkoxy group having 1 to 4 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, a butoxy group and the like, and a methoxy group is preferable.

As the biimidazole compound, for example, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis (2, 3-dichlorobenzene -4,4',5,5'-tetraphenylbiimidazole (for example, refer to JPH06-75372-A, JPH06-75373-A, etc.), 2,2'-bis(2-chlorophenyl)- 4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(alkoxyphenyl)biimidazole , 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl) -4,4',5,5'-tetrakis(trialkoxyphenyl)biimidazole (for example, refer to JPS48-38403-B, JPS62-174204-A, etc.), 4, 4'5, 5' An imidazole compound in which a phenyl group at the - position is substituted with an alkoxycarbonyl group (for example, refer to JPH07-10913-A, etc.) and the like. Among them, a compound represented by the following formula and a mixture of these are preferable.

As mentioned above For the compound, for example, 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-three , 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-three , 2,4-bis(trichloromethyl)-6-sunflower-1,3,5-three , 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-three , 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)vinyl]-1,3,5-three , 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)vinyl]-1,3,5-three , 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl]-1,3,5-three , 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl)-1,3,5-three Wait.

The above-mentioned mercaptophosphine oxide compound may, for example, be 2,4,6-trimethylbenzylidenediphenylphosphine oxide.

Further, as the polymerization initiator (D), benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether and other benzoin compounds; benzophenone, o-benzhydryl benzoic acid Methyl ester, 4-phenylbenzophenone, 4-benzylindolyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tris-butylcarbonyl)benzophenone a benzophenone compound such as 2,4,6-trimethylbenzophenone; an anthraquinone compound such as 9,10-phenanthrenequinone, 2-ethylhydrazine, camphorquinone; 10-butyl-2-chloroacridone , benzil, methyl phenylglyoxylalte, titanium oxide (titanocene) compound, and the like. These are preferably used in combination with a polymerization initiation aid (D1) (particularly an amine) to be described later.

The content of the polymerization initiator (D) is desirably 1 to 30% by mass, and more desirably 5 to 20% by mass based on the total amount of the solid content.

In addition, the content of the polymerization initiator (D) is preferably from 1 to 50 parts by mass, more preferably from 10 to 45 parts by mass, based on 100 parts by mass of the total of the resin (B) and the polymerizable compound (C). More preferably, it is 20 to 40 parts by mass.

<Polymerization starter (D1)>

The polymerization initiation aid (D1) is a compound for promoting polymerization of a polymerizable compound which starts polymerization by a polymerization initiator, or a sensitizer. When the polymerization initiator (D1) is contained, it is usually used in combination with the polymerization initiator (D).

The polymerization starting aid (D1) may, for example, be an amine compound, an alkoxy fluorene compound, a thioxanthone compound, a carboxylic acid compound or the like.

As the aforementioned amine compound, there may be mentioned triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, 4-di Methylamino benzoic acid isoflavone Ester, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis (dimethyl Amino) benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(ethylmethylamino) Benzophenone and the like, among which 4,4-bis(diethylamino)benzophenone is particularly preferred. Commercial products such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) can also be used.

The alkoxy hydrazine compound may, for example, be 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethylanthracene or 2-ethyl -9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, 2-ethyl-9,10-dibutoxyanthracene, and the like.

Examples of the aforementioned thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, and 2,4-dichlorothioxanthone. 1-Chloro-4-propoxythioxanthone and the like.

Examples of the aforementioned carboxylic acid compound include phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, and dimethylphenylthioacetic acid. , methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthyl Sulfuric acid, N-naphthylglycine, naphthoxyacetic acid, and the like.

When the polymerization initiator (D1) is used, the content thereof is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass based on 100 parts by mass of the total of the resin (B) and the polymerizable compound (C). Share. When the amount of the polymerization initiation aid (D1) is within this range, a colored patterning coating film can be formed with higher sensitivity, and the productivity of the color filter tends to be improved.

<thiol compound (T)>

The thiol compound (T) is a compound having -SH in the molecule.

For a compound having one -SH in the molecule, for example, a 2-thio group can be cited. Oxazole, 2-thiothiazole, 2-thiobenzimidazole, 2-thiobenzothiazole, 2-thiobenzophenone Oxazole, 2-thionicotinic acid, 2-thiopyridine, 2-thiopyridin-3-ol, 2-thiopyridine-N-oxide, 4-amino-6-hydroxy-2-thio Pyrimidine, 4-amino-6-hydroxy-2-thiothiopyrimidine, 4-amino-2-thiopyrimidine, 6-amino-5-nitroso-2-thiouracil, 4,5 -diamino-6-hydroxy-2-thiopyrimidine, 4,6-diamino-2-thiopyrimidine, 2,4-diamino-6-thiopyrimidine, 4,6-dihydroxy- 2-thiopyrimidine, 4,6-dimethyl-2-thiopyrimidine, 4-hydroxy-2-thio-6-methylpyrimidine, 4-hydroxy-2-thio-6-propylpyrimidine, 2-thio-4-methylpyrimidine, 2-thiopyrimidine, 2-thiouracil, 3,4,5,6-tetrahydropyrimidin-2-thiol, 4,5-diphenylpyrazole- 2-thiol, 2-thiopyrazole, 2-thio-1-methylpyrazole, 4-amino-3-indolyl-5-thio-1,2,4-triazole, 3- Amino-5-thio-1,2,4-triazole, 2-methyl-4H-1,2,4-triazole-3-thiol, 4-methyl-4H-1,2,4 Triazole-3-thiol, 3-thiol 1H-1,2,4-triazole-3-thiol, 2-amino-5-thio-1,3,4-thiadiazole, 5 -Amino-1,3,4-thiadiazole-2-thiol, 2,5-dithio-1,3,4-thiadiazole, (furan-2-yl)methanethiol, 2- Thio-5-thiazolidine (2-sulfanyl-5-thiazolido) Ne), 2-sulfanyl thiazoline, 2-sulfanyl-4(3H)-quinazolinone, 1-phenyl-1H- Tetrazolium-5-thiol, 2-quinoline thiol, 2-thio-5-methylbenzimidazole, 2-thio-5-nitrobenzimidazole, 6-amino-2-thio Benzothiazole, 5-chloro-2-thiobenzothiazole, 6-ethoxy-2-thiobenzothiazole, 6-nitro-2-thiobenzothiazole, 2-thionaphthyl imidazole 2-thionaphthyl Oxazole, 3-thio-1,2,4-triazole, 4-amino-6-thiopyrazolo[2,4-d]pyridine, 2-amino-6-anthracenethiol, 6- Thioquinone, 4-thio-1H-pyrazolo[2,4-d]pyrimidine, and the like.

Examples of the compound having two or more -SH in the molecule include hexane dithiol, decane dithiol, 1,4-bis(methylthio)benzene, butanediol bis (3-sulfuric acid). Propionate), butanediol bis(3-thioacetate), ethylene glycol bis(3-thioacetate), trimethylolpropane tris(3-thioacetate) , butanediol bis(3-thiopropionate), trimethylolpropane tris(3-thiopropionate), trimethylolpropane tris(3-thioacetate), neopentyl Tetraol tetrakis(3-thiopropionate), pentaerythritol tetrakis(3-thioacetate), trishydroxyethyltris(3-thiopropionate), pentaerythritol tetra(3) -thiobutyrate), 1,4-bis(3-thiobutyloxy)butane, and the like.

In the case of the thiol compound (T), a compound having one -SH in the molecule is preferred.

The content of the thiol compound (T) is preferably from 0.5 to 20 parts by mass, more preferably from 1 to 15 parts by mass, per 100 parts by mass of the polymerization initiator (D). When the content of the thiol compound (T) is within this range, the sensitivity is high and the developability tends to be good.

<Solvent (E)>

The solvent (E) is not particularly limited, and a solvent which is generally used in the art can be used. For example, an ester solvent (a solvent containing -COO- in the molecule, a solvent containing no -O-), an ether solvent (a solvent containing -O- in the molecule, a solvent containing no -COO-), an ether ester solvent (molecular inclusion - Solvent for COO- and -O-), ketone solvent (-CO-, solvent without -COO-), alcohol solvent (OH in the molecule, -O-, -CO- and - a solvent of COO-), an aromatic hydrocarbon solvent, a guanamine solvent, dimethyl hydrazine or the like.

Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, and isoamyl acetate. Ester, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetate, ethyl acetate Cyclohexanol acetate, γ-butyrolactone, and the like.

As the ether solvent, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, and the like are mentioned. Ethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butyl Alcohol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-two Alkane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, methoxy Anisole, phenetole, methylmethoxybenzene, and the like.

Examples of the ether ester solvent include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, and 3-methoxypropene. Methyl ester, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, 2-methoxypropane Ethyl acetate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropanoate, 2 - Ethoxy-2-methylpropionic acid ethyl ester, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether Acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol Monobutyl ether acetate, dipropylene glycol methyl ether acetate, and the like.

As the ketone solvent, there may be mentioned 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2. - Pentanone, cyclopentanone, cyclohexanone, isophorone, and the like.

Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, glycerin and the like.

Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, 1,3,5-trimethylbenzene and the like.

Examples of the guanamine solvent include N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone and the like.

These solvents may be used singly or in combination of two or more.

Among the above-mentioned solvents, an organic solvent having a boiling point of from 120 ° C to 180 ° C at a boiling point of 1 atm is preferred from the viewpoint of coatability and drying property. Among them, especially propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, ethylene glycol monobutyl ether, two Ethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 3-methoxybutyl acetate, 3-methoxy-1-butanol, 4-hydroxy-4-methyl-2-pentanone And N,N-dimethylformamide is ideal, and propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethylene glycol monobutyl ether, dipropylene glycol methyl ether acetate, lactate B The ester, 3-methoxybutyl acetate, 3-methoxy-1-butanol and ethyl 3-ethoxypropionate are more preferred.

The content of the solvent (E) relative to the colored photosensitive resin group The total amount of the product is desirably 70 to 95% by mass, more desirably 75 to 92% by mass. In other words, the solid content of the colored photosensitive resin composition is desirably 5 to 30% by mass, more desirably 8 to 25% by mass.

When the content of the solvent (E) is in the above range, the flatness at the time of coating is good, and when the color filter is formed, the color density is sufficient, so that the display property tends to be good.

<Leveling agent (F)>

Examples of the leveling agent (F) include a polyfluorene-based surfactant, a fluorine-based surfactant, and a polyfluorene-based surfactant having a fluorine atom. These may have a polymerizable group in the branch.

The polyoxo-based surfactant may, for example, be a surfactant having a siloxane coupling in the molecule. Specifically, Toray Silicone DC3PA, same as SH7PA, with DC11PA, with SH21PA, with SH28PA, with SH29PA, with SH30PA, with SH8400 (trade name; Toray DOW Corning (share) system); KP321, KP322 , KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.); TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452 and TSF4460 (manufactured by Momentive Performance Materials Japan Co., Ltd.).

The above-mentioned fluorine-based surfactant may, for example, be a surfactant having a fluorocarbon chain in the molecule. Specifically, Fluorad (registered trademark) FC430, FC431 (Sumitomo 3M (share) system); Megafac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, and the same R30, same as RS-718-K (DIC system); Eftop (registered trademark) EF301, same as EF303, with EF351, with EF352 (Mitsubishi Materials Electronics Co., Ltd.); Surflon (registered trademark) S381, same as S382, with SC101, with SC105 (asahi Glass) Same as E5844 (Daikin Fine Chemicals Research Institute Co., Ltd.).

Examples of the polyfluorene-based surfactant having a fluorine atom include a surfactant having a siloxane chain and a fluorocarbon chain in the molecule. Specific examples include Megafac (registered trademark) R08, BL30, F475, F477, and F443 (DIC).

The content of the leveling agent (F) is preferably 0.001% by mass or more and 0.2% by mass or less, more preferably 0.002% by mass or more and 0.1% by mass or less, and more preferably 0.005% by mass or more, based on the total amount of the coloring photosensitive resin composition. 0.05% by mass or less. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

<Adhesion Promoter (G)>

Examples of the adhesion promoter (G) include ethylene trimethoxy decane, ethylene triethoxy decane, ethylene tris(2-methoxyethoxy) decane, and 3-epoxypropoxy propyl acrylate. Trimethoxymethoxydecane, 3-glycidoxypropylmethyldimethoxydecane, 3-glycidoxypropylmethyldimethoxydecane, 3-glycidoxypropyl Diethoxy decane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxydecane, 3-chloropropylmethyldimethoxydecane, 3-chloropropyltrimethoxydecane, 3-methylpropenyloxypropyltrimethoxydecane, 3-mercaptopropyltrimethoxydecane, 3-thiopropyltrimethoxydecane, 3-isocyanatepropyltriethoxydecane, N-2 -(Aminoethyl)-3-aminopropylmethyldimethoxydecane, N-2-(aminoethyl)-3-aminopropylmethyldiethyl Oxydecane, N-2-(aminoethyl)-3-aminopropyltrimethoxydecane, N-2-(aminoethyl)-3-aminopropylmethyldiethoxydecane , 3-aminopropyltrimethoxydecane, 3-aminopropyltriethoxydecane, N-phenyl-3-aminopropyltrimethoxydecane, N-phenyl-3-aminopropyl Triethoxy decane and the like.

The content of the adhesion promoter (G) is preferably 0.1% by mass or more and 5% by mass or less based on the total amount of the solid content, and is preferably 0.2% by mass or more and 2% by mass or less. When the content of the adhesion promoter (G) is within the above range, the adhesion to the substrate can be improved.

<Other ingredients>

The colored photosensitive resin composition of the present invention may contain a filler, other polymer compound, adhesion promoter, antioxidant, light stabilizer, chain transfer agent, etc., which are known in the art, as needed.

<Method for Producing Colored Photosensitive Resin Composition>

The colored photosensitive resin composition of the present invention can be, for example, a coloring agent (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), a solvent (E), and the like. The thiol compound (T), the leveling agent (F), the polymerization starting aid (D1), the adhesion promoter (G) and other components used in the preparation are mixed.

The pigment is preferably mixed with a part or all of the solvent (E) in advance and dispersed by using a bead mill or the like until the average particle diameter of the pigment is about 0.2 μm or less. At this time, a part or all of the above-mentioned pigment dispersant and resin (B) may be blended as needed. The pigment dispersion liquid thus obtained is mixed with the remaining components to a predetermined concentration, and the color light of the purpose can be modulated. Sensitive resin composition.

It is preferable to filter the mixed color-sensitive photosensitive resin composition using a filtration membrane having a pore diameter of about 0.1 to 10 μm.

<Method of Manufacturing Color Filter>

The method of producing the colored patterned coating film from the colored photosensitive resin composition of the present invention includes a micro-etching method, an ink jet method, a printing method, and the like. Among them, the lithography method is ideal. The lithography method is a method in which the colored photosensitive resin composition is applied onto a substrate and dried to form a colored composition layer, and the colored composition layer is exposed and developed through a photomask. In the lithography method, a colored coating film of a cured product of the colored composition layer can be formed by using a mask without exposure and/or no development. The colored patterned coating film or colored coating film thus formed is the color filter of the present invention.

The film thickness of the produced color filter is not particularly limited, and can be appropriately adjusted depending on the purpose, use, and the like, and is, for example, 0.1 to 30 μm, preferably 0.1 to 20 μm, and more desirably 0.5 to 6 μm.

As the substrate, quartz glass, borosilicate glass, aluminum silicate glass, a glass plate such as soda-lime glass coated with cerium oxide; polycarbonate, polymethyl methacrylate, A resin plate such as polyethylene terephthalate; and a substrate such as an aluminum, silver, silver/copper/palladium alloy film formed on the substrate. On these substrates, other color filter layers, resin layers, transistors, circuits, and the like can be formed.

The formation of the respective color pixels by the lithography method can be carried out by known or conventional devices and conditions. For example, it can be produced by the method described below.

First, the colored photosensitive resin composition is applied onto a substrate, and dried by heating (prebaking) and/or drying under reduced pressure to remove volatile components such as a solvent and drying to obtain a smooth colored composition layer.

Examples of the coating method include a spin coating method, a slit coating method, a slit, and a slit and spin coating method.

The temperature at the time of heat drying is preferably 30 to 120 ° C, more preferably 50 to 110 ° C. Further, in terms of heating time, it is preferably from 10 seconds to 60 minutes, and more preferably from 30 seconds to 30 minutes.

When drying under reduced pressure, it is preferably carried out at a temperature of from 20 to 25 ° C under a pressure of 50 to 150 Pa.

The film thickness of the coloring composition layer is not particularly limited, and may be appropriately selected depending on the film thickness of the intended color filter.

Next, the colored composition layer is exposed through a photomask for forming a color-patterned coating film for the purpose of formation. The pattern on the photomask is not particularly limited, and a pattern suitable for the purpose of use can be used.

As the light source for exposure, a light source which generates light of a wavelength of 250 to 450 nm is desirable. For example, a filter that intercepts light in a wavelength range of less than 350 nm may be used, or a light of about 436 nm, about 408 nm, or about 365 nm may be used to take out a band-pass filter of these wavelength regions. ) and selectively removed.

Specifically, a mercury lamp, a light-emitting diode, a metal halide lamp, a halogen lamp, etc. are mentioned.

In order to uniformly illuminate the entire surface of the exposed surface, or to make the substrate on which the mask and the coloring composition layer are formed, the position can be correctly adjusted to use the mask. Exposure devices such as aligners and steppers are ideal.

The colored patterned coating layer is formed on the substrate by developing the exposed colored composition layer in contact with the developing solution. The unexposed portion of the colored composition layer was dissolved in a developing solution to be removed by development.

As the developer, for example, an aqueous solution of a basic compound such as potassium hydroxide, sodium hydrogencarbonate, sodium carbonate or tetramethylammonium hydroxide is preferred. The concentration in the aqueous solution of these basic compounds is desirably 0.01 to 10% by mass, more desirably 0.03 to 5% by mass. Further, the developer may contain a surfactant.

The developing method may be any one of a puddle method, a dipping method, and a spraying method. Further, the substrate can be tilted at an arbitrary angle during development.

After development, it is ideal to wash with water.

Further, it is preferable to pattern the obtained colored coating film and perform post-baking. The post-baking temperature is preferably 150 to 250 ° C, more preferably 160 to 235 ° C. The post-baking time is ideal from 1 to 120 minutes, and more preferably from 10 to 60 minutes.

According to the colored photosensitive resin composition of the present invention, in particular, the generation of the residue or the residual film is small, and thus a color filter having few defects can be produced. The color filter is useful as a color filter for use as a display device (for example, a liquid crystal display device, an organic EL device, an electronic paper, etc.) and a solid image sensor.

Example

Next, the present invention will be described more specifically by way of examples. In the examples, "%" and "parts" indicate the mass % and mass parts unless otherwise stated.

Synthesis Example 1

In a flask equipped with a stirrer, a thermometer, a reflux condenser, and a dropping funnel, nitrogen gas was passed through at 0.02 L/min to form a nitrogen atmosphere, and 257 parts by mass of propylene glycol monomethyl ether acetate was charged, and heated to 70 with stirring. °C. Then, 8 parts of acrylic acid, 70 parts of N-cyclohexylmaleimide, 3,4-epoxytricyclo[5.2.1.0 ^2.6 ]decane-8-acrylate and 3,4-epoxy acrylate 32 parts by mass of a mixture of tricyclo [5.2.1.0 ^2.6 ]decane-9-ester (containing a molar ratio of 50:50), dissolved in 140 parts by mass of propylene glycol monomethyl ether acetate to prepare a solution, This solution was dropped into a flask kept at 70 ° C for 4 hours using a dropping funnel.

On the other hand, 15 parts by mass of a polymerization initiator 2,2'-azobis(2,4-dimethylvaleronitrile) was dissolved in a solution of 225 parts by mass of propylene glycol monomethyl ether acetate, and another The dropping funnel took 4 hours to drip into the flask. After completion of the dropwise addition of the solution of the polymerization initiator, the mixture was kept at 70 ° C for 4 hours, and then cooled to room temperature to obtain a resin B1 solution having a solid content of 26.7% by mass. The weight average molecular weight of the resin B1 was 6.8 × 10 ³ , the molecular weight distribution was 2.23, and the acid value in terms of solid content was 114 mg-KOH/g. The resin B1 has the following structural unit.

Synthesis Example 2

In a flask equipped with a reflux condenser, a dropping funnel and a stirrer, an appropriate amount of nitrogen gas was passed in place of a nitrogen atmosphere, and 371 parts of propylene glycol monomethyl ether acetate was placed, and the mixture was heated to 85 ° C while stirring. Next, 54 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 ^2.6 ]decane-8-acrylate and 3,4-epoxytricyclo[5.2.1.0 ^2.6 ]decane-9 a mixed solution prepared by dissolving 225 parts of a mixture of esters (containing 50:50 by molar ratio), 81 parts of vinyl toluene (mixture of isomers), and 80 parts of propylene glycol monomethyl ether acetate. It was dropped into the flask over 4 hours.

On the other hand, 30 parts of the polymerization initiator 2,2-azobis(2,4-dimethylvaleronitrile) was dissolved in 160 parts of propylene glycol monomethyl ether acetate, and it took 5 hours to drip in. . After the completion of the dropwise addition of the initiator solution, the mixture was kept at 85 ° C for 4 hours, and then cooled to room temperature to obtain a copolymer solution. This copolymer was used as the resin B2. The solid content of the resin B2 solution was 37.5%, and the viscosity measured by the B-type viscometer (23 ° C) was 246 mPa. s. The weight average molecular weight of the resin B2 was 1.06 × 10 ⁴ , the molecular weight distribution was 2.01, and the acid value in terms of solid content was 115 mg-KOH/g. The resin B2 has the following structural unit.

Synthesis Example 3

In a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel, and a gas introduction tube, 200 parts of propylene glycol monomethyl ether acetate was introduced. Thereafter, nitrogen gas was introduced into the flask through a gas introduction tube, and the atmosphere inside the flask was replaced with nitrogen. After the solution in the flask was heated to 70 ° C, 144 parts of benzyl methacrylate, 30 parts of tricyclo [5.2.1.0 ^2.6 ] decyl methacrylate, 35 parts of methacrylic acid, and 5.2 parts of azobisisobutyronitrile were added. A mixture of 213 parts of propylene glycol monomethyl ether acetate was added dropwise to the flask over a period of 2 hours using a dropping funnel, and the mixture was stirred at 100 ° C for 5 hours after the completion of the dropwise addition. After completion of the dropwise addition of the solution of the polymerization initiator, it was kept at 70 ° C for 4 hours, and then cooled to room temperature to obtain a 33.6% solution of the resin B3 in a solid form. The weight average molecular weight of the resin B3 was 1.03 × 10 ⁴ , the molecular weight distribution was 2.16, and the acid value in terms of solid content was 110.4 mg-KOH/g. The resin B3 has the following structural unit.

Synthesis Example 4

In a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel, and a gas introduction tube, 200 parts of propylene glycol monomethyl ether acetate was introduced. Thereafter, nitrogen gas was introduced into the flask through a gas introduction tube, and the atmosphere inside the flask was replaced with nitrogen. After the solution in the flask was heated to 70 ° C, 144 parts of benzyl methacrylate, 30 parts of tricyclo [5.2.1.0 ^2.6 ] decyl methacrylate, 42 parts of acrylic acid, 5.2 parts of azobisisobutyronitrile and propylene glycol were added. A mixture of 213 parts of monomethyl ether acetate was dropped into the flask over 2 hours using a dropping funnel, and after the completion of the dropwise addition, the mixture was stirred at 100 ° C for 5 hours. After completion of the dropwise addition of the solution of the polymerization initiator, it was kept at 70 ° C for 4 hours, and then cooled to room temperature to obtain a 34.1% solution of the resin B4 in a solid form. The weight average molecular weight of the resin B4 was 1.13 × 10 ⁴ , the molecular weight distribution was 2.18, and the acid value in terms of solid content was 108.5 mg-KOH/g. The resin B4 has the following structural unit.

The measurement of the polystyrene-equivalent weight average molecular weight (Mw) and the number average molecular weight (Mn) of the resin was carried out under the following conditions by the GPC method.

Device: HLC-8120GPC (Tosoh Co., Ltd.)

Column: TSK-GELG2000HXL

Column temperature: 40 ° C

Solvent: THF

Flow rate: 1.0ml/min

Solid concentration of test liquid: 0.001 to 0.01% by mass

Injection volume: 50μL

Detector: RI

Standard materials for calibration: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (made by Tosoh Corporation)

The ratio (Mw/Mn) of the weight average molecular weight and the number average molecular weight in terms of polystyrene obtained above was defined as a molecular weight distribution.

[Modulation of Pigment Dispersion A1]

Propylene glycol monomethyl ether acetate 78.3 parts

The above was mixed, and the pigment was sufficiently dispersed using a bead mill to obtain a pigment dispersion A1.

[Modulation of Pigment Dispersion A2]

The above was mixed, and the pigment was sufficiently dispersed using a bead mill to obtain a pigment dispersion A2.

[Modulation of Pigment Dispersion A3]

The above was mixed, and the pigment was sufficiently dispersed using a bead mill to obtain a pigment dispersion A3.

[Modulation of Pigment Dispersion A4]

The above was mixed, and the pigment was sufficiently dispersed using a bead mill to obtain a pigment dispersion A4.

(Modulation of Pigment Dispersion A5)

The above was mixed, and the pigment was sufficiently dispersed using a bead mill to obtain a pigment dispersion A5.

Examples 1 to 8 and Comparative Example 1

[Preparation of coloring photosensitive resin composition]

The components described in the first table were mixed to obtain a colored photosensitive resin composition.

In the first table, the column of "resin (B)" indicates the content (parts) of the solid content conversion.

The coloring agent (A) is prepared by mixing the pigment dispersions A1 to A5 in advance. The "colorant (A)" column in the first table indicates the content (parts) of the coloring agent contained in the pigment dispersion liquid used.

The column of "acrylic dispersant" shows the total amount (parts) of the acrylic dispersing agent contained in the pigment dispersion liquid used.

The column of "solvent (E)" indicates the total amount (parts) of each solvent contained in the coloring photosensitive resin composition.

In the first table, the respective components are as follows.

Colorant (A): A1: C.I. Pigment Green 58 (Forehead Dispersion A1)

Colorant (A): A2: C.I. Pigment Yellow 138 (Pigment Dispersion A2)

Colorant (A): A3: C.I. Pigment Yellow 150 (Pigment Dispersion A3)

Colorant (A): A4: C.I. Pigment Red 177 (Pigment Dispersion A4)

Colorant (A): A5: C.I. Pigment Blue 15:6 (Pigment Dispersion A5)

Resin (B): B1: Resin B1

Resin (B): B2: Resin B2

Resin (B): B3: Resin B3

Resin (B): B4: Resin 84

Resin (B): B5: a resin obtained by copolymerizing 21 parts of methacrylic acid with 70 parts of benzyl methacrylate, and then adding 9 parts of glycidyl methacrylate to the presence of a triethanolamine catalyst (weight) Average molecular weight: 1.2 × 10 ⁴ , acid value converted by solid content: 80 mg-KOH / g)

Polymerizable compound (C): C1: dineopentaerythritol hexaacrylate (KAYARAD (registered trademark); DPHA: Nippon Chemical Co., Ltd.)

Polymerizable compound (C): C2: dipentaerythritol pentaacrylate

Polymerization initiator (D): D1: N-benzylidenyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine (Irgacure (registered trademark) OXE01; BASF Company system; O-mercaptopurine compound)

Polymerization initiator (D): D2: 2-methyl-2-(N-morpholinyl)-1-(4-methylthiophenyl)propan-1-one (Irgacure (registered trademark) 907; BASF company; phenyl ketene compound)

Polymerization initiator (D): D3: a mixture of compounds represented by the following formula (CHEMCURE-TCDM; manufactured by Chembridge; biimidazole compound)

Polymerization initiation aid (D1): 4,4'-bis(diethylamino)benzophenone (EAB-F; manufactured by Hodogaya Chemical Industry Co., Ltd.)

Thiol compound (T): D1a: 2-thiobenzothiazole (SOXINOL (registered trademark) M: Sumitomo Chemical Co., Ltd.: a compound represented by the following formula)

Adhesion promoter (G): D1b: 3-methacryloxypropyltrimethoxydecane (KBM-503: Shin-Etsu Chemical Co., Ltd.)

Solvent (E): E1: propylene glycol monomethyl ether acetate

Solvent (E): E2: ethyl lactate

Solvent (E): E3: ethylene glycol monobutyl ether

Surfactant (F): Polyether modified oyster sauce (Dongli. Dow Corning (stock) system; SH8400)

[Production of patterned coating film]

The colored photosensitive resin composition was applied by a spin coating method on a glass substrate (Eagle XG; manufactured by Corning Incorporated) of 2 inches square, and then prebaked at 100 ° C for 3 minutes to form a colored composition layer. After cooling, the interval between the substrate on which the colored composition layer was formed and the mask made of quartz glass was set to 100 μm, and an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.) was used, and in an atmosphere, 30 mJ/cm. The exposure amount of ² (365 nm reference) irradiated light. As for the photomask, a photomask formed with a line and a line-and-space pattern of 50 μm was used. After the light was irradiated, the coating film was immersed in an aqueous developing solution containing 0.12% of a nonionic surfactant and 2% of sodium carbonate at 24 ° C for development, and after washing with water, in an oven, After baking at 230 ° C for 30 minutes, a colored patterned coating film was obtained.

[developability evaluation]

The glass substrate on which the colored patterned coating film was formed was observed by an optical microscope, and when no residue or residual film was observed in the unexposed portion, it was ○, and when it was seen, it was ×. The results are shown in Table 2.

[Adhesion evaluation]

The colored patterned coating film was observed by an optical microscope, and when it was not observed that peeling was observed as ○, when a part of the colored patterned coating film was peeled off, it was regarded as Δ, and when the colored patterned coating film was completely peeled off, it was ×. . The results are shown in Table 2.

[Measurement of film thickness]

With respect to the obtained colored patterned coating film, the film thickness was measured using a film thickness measuring device (DEKTAK3; manufactured by Nippon Vacuum Technology Co., Ltd.). The results are shown in Table 2.

[Colorimetric evaluation]

With respect to the obtained colored patterned coating film, the color separation was measured using a color measuring machine (OSP-SP-200; manufactured by Olympus Co., Ltd.), and the xy chromaticity coordinate of the XYZ color system of the CIE was measured using the characteristic function of the C light source (x, y) and tristimulus value Y. A larger Y value indicates a higher brightness. The results are shown in Table 2.

According to the colored photosensitive resin composition of the present invention, the coloring patterned coating film has excellent developability when formed.

Claims (5)

A colored photosensitive resin composition containing a colorant, a resin, a polymerizable compound, a polymerization initiator, and a solvent, and the colorant contains CI Pigment Green 58, which is composed of a yellow pigment, a blue pigment, a red pigment, a purple pigment, and an orange pigment. At least one selected from the group formed, the content of the colorant is 20% by mass or more and 50% by mass or less based on the total amount of the solid content. The colored photosensitive resin composition according to claim 1, wherein the resin is an addition polymerization of at least one structural unit selected from the group consisting of a source of a free unsaturated carboxylic acid and an unsaturated carboxylic anhydride. Things. The colored photosensitive resin composition according to the first or second aspect of the invention, wherein the ratio of the content of the resin to the content of the polymerizable compound is from 20:80 to 80:20 on a mass basis. A color filter formed of the colored photosensitive resin composition according to any one of claims 1 to 3. A display device comprising the color filter of claim 4 of the patent application.