TWI617885B - Colored photosensitive resin composition - Google Patents

Abstract

The invention provides a colored photosensitive resin composition. The colored photosensitive resin composition contains a colorant, a resin, a polymerizable compound, a polymerization initiator, and a solvent. The colorant contains CI Pigment Green 58, a yellow pigment, and a blue pigment. At least one selected from the group consisting of red pigments, purple pigments, and orange pigments; the content of the colorant is 20% by mass or more and 50% by mass or less with respect to the total 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 a color filter used in the manufacture of a display device such as a liquid crystal display panel, an electroluminescent panel, and a plasma display panel. For such a colored photosensitive resin composition, there is known a composition containing CI Pigment Green 58 and CI Pigment Yellow 138 and CI Pigment Red 177 as a colorant, and the content of the colorant relative to the color photosensitivity The solid content of the resin composition was 14% by mass. (JP2011-118051-A).

In the conventionally known colored photosensitive resin composition, when a colored patterned coating film is formed by a lithographic etching method, unexposed portions cannot be sufficiently removed during development, and residues or residual films may be generated.

The present invention includes the following inventions.

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

[2] The colored photosensitive resin composition according to [1], wherein the resin is an addition polymer having at least one structural unit selected from the group consisting of an 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 20:80 to 80:20 on a mass basis.

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

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

The colored photosensitive resin composition according to the present invention has excellent developability when a colored patterned coating film is formed by a lithographic etching 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 an adhesion promoter (G). One less is ideal.

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

<Colorant (A)>

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

As for 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.

Examples of the blue pigment include C.I. Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60, 80, and the like.

As for 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.

Examples of the purple material include C.I. Pigment Violet 1, 19, 23, 29, 32, 36, 38, and the like, and C.I. Pigment Violet 23 is preferable.

As for 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 can be cited. Ideally, CI pigment orange 38 is used. .

These pigments can be subjected to rosin treatment if necessary, surface treatments such as pigment derivatives with acidic or basic groups introduced, graft treatment of pigment surfaces with polymer compounds, and micronization treatments such as sulfuric acid micronization. Alternatively, it can be used to remove impurities and washed with an organic solvent, water, or the like, or to remove ionic impurities by an ion exchange method or the like. The particle diameter of the pigment is preferably each uniform.

These pigments can be a pigment dispersion in a state where they are uniformly dispersed in a pigment dispersant solution by containing a pigment dispersant and performing a dispersion treatment. The pigments can be separately dispersed, or they can be mixed and dispersed.

Examples of the pigment dispersant include pigment dispersants such as cationic, anionic, nonionic, amphoteric, polyester, polyamine, and acrylic. These pigment dispersants can be used alone or in combination of two or more. Examples of the pigment dispersant include the trade names KP (Shin-Etsu Chemical Industry Co., Ltd.), Flowlen (Kyoei Chemical Co., Ltd.), Solsperse (Zeneca (Co.)), EFKA (CIBA), Ajisper (made by Ajinomoto Fine-Techno) and Disperbyk (made by BYK Chemie).

When a pigment dispersant is used, the amount used is preferably 100 parts by mass or less, and 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 within 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 20 to 99% by mass, and more preferably 30 to 95% by mass relative to the total amount of the colorant (A).

The content of the yellow pigment is preferably from 0.1 to 80% by mass, and more preferably from 15 to 60% by mass relative to 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 relative to the total amount of the colorant (A). % Is more ideal.

<Resin (B)>

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

Resin [K1] at least one (a) (hereinafter sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides, and cyclic ethers having 2 to 4 carbon atoms Structure and copolymer of ethylenically unsaturated monomer (b) (hereinafter sometimes referred to as "(b)"); tree finger [K2] (a) and (b), and Copolymer of monomers (c) (but different from (a) and (b).) (Hereinafter sometimes referred to as "(c)"); resins [K3] (a) and (c) Copolymer; resin [K4] resin that reacts (a) and (c) copolymer with (b); resin [K5] resin that reacts (b) and (c) copolymer with (a); resin [K6] A resin in which the copolymer of (b) and (c) reacts with (a) and then reacts with carboxylic anhydride.

As for (a), specifically, for example, acrylic acid may be cited, Unsaturated monocarboxylic acids such as methacrylic acid, 2-butenoic acid, o-, m-, and p-ethylene benzoic acid; maleic acid, fumaric acid, citraconic acid, mesaconic acid ), Itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyl Unsaturated dicarboxylic acids such as tetrahydrophthalic acid, 1,4-cyclohexene dicarboxylic acid; methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo [2.2.1] heptane -2-ene, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene, 5-carboxy-5-methylbicyclo [2.2.1] hept-2-ene, 5-carboxy-5-ethyl Methylbicyclo [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 -Bicyclic unsaturated compounds containing carboxyl groups such as olefins; 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 anhydride and other unsaturated dicarboxylic anhydrides; succinic acid mono [2- (meth) acryloxyethyl], phthalic acid mono [2- (meth) acryloxyethyl] ] Unsaturated mono [(meth) acryloxyalkyl] esters of polyvalent carboxylic acids with an equivalent of 2 or more; unsaturated like a- (hydroxymethyl) acrylic acid containing hydroxyl and carboxyl groups in the same molecule Acrylates, etc.

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

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

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

Examples of (b) include, for example, a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)"), and having propylene oxide Group (oxetanyl) and ethylenically unsaturated bonded monomer (b2) (hereinafter sometimes referred to as "(b2)"), a monomer (b3) having a tetrahydrofuranyl group and ethylenically unsaturated bond (hereinafter sometimes referred to Called "(b3)").

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

As for (b1-1), glycidyl (meta) acrylate, β-methacrylic acid (meth) acrylate, and β-ethyl (meth) acrylate can be listed. Glycidyl glycidyl ester, glycidyl vinyl ether, o-vinyl benzyl glycidyl ether, m-vinyl benzyl glycidyl ether, p-vinyl benzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether , 2,3-bis (glycidyloxymethyl) styrene, 2,4-bis (glycidyloxymethyl) styrene, 2,5-bis (glycidyloxymethyl) ) Styrene, 2,6-bis (glycidyloxymethyl) styrene, 2,3,4-tris (glycidyloxymethyl) styrene, 2,3,5-tris (Glycidyloxymethyl) styrene, 2,3,6-tris (glycidyloxymethyl) styrene, 3,4,5-tris (glycidyloxymethyl) Styrene, 2,4,6-tris (glycidoxymethyl) styrene and the like.

Examples of (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celoxide2000; manufactured by Daicel), (methyl ) 3,4-epoxycyclohexyl methyl acrylate (for example, Cyclomer A400; manufactured by Daicel); 3,4-epoxy cyclohexyl methyl (meth) acrylate (for example, Cyclomer M100; Daicel ( (Products)), compounds represented by formula (I), compounds represented by formula (II), and the like.

[In formulae (I) and (II), R ^a and R ^b represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the 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 a bond with O].

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

Examples of the alkyl group having a hydrogen atom substituted with a hydroxy group include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1- hydroxyl Methyl-1-methylethyl, 2-hydroxy-1-methylethyl, 1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl, 4-hydroxybutyl and the like.

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

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

As for X ^a and X ^b , a single bond, methylene, ethylidene, * -CH ₂ -O- and * -CH ₂ CH ₂ -O- are preferable, and more preferably, single bond and * -CH ₂ CH ₂ -O- (* indicates a bond with O).

Examples of the compound represented by the formula (I) include any compound represented by the formula (I-1) to the formula (I-15). Among them, formula (I-1), formula (I-3), formula (I-5), formula (I-7), formula (I-9) or formula (I-11) to formula (I- The compound represented by 15) is preferable, and the compound represented by formula (I-1), formula (I-7), formula (I-9) or formula (I-15) is more preferable.

Examples of the compound represented by the formula (II) include compounds represented by any one of the formulae (II-1) to (II-15). Among them, especially formula (II-1), formula (II-3), formula (II-5), formula (II-7), formula (II-9) or formula (II-11) to formula (II- The compound represented by 15) is preferable, and the compound represented by formula (II-1), formula (II-7), formula (II-9) or formula (11-15) is more preferable.

The compound represented by the formula (I) and the compound represented by the formula (II) may be used alone, or a compound represented by the formula (I) and a compound represented by the formula (II) may be used in combination. 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 5:95 to 95: 5, and more preferably 10:90 to 90:10. Even more desirable is 20:80 to 80:20.

As for (b2), a monomer having a propylene oxide group and a (meth) acryloxy group is more preferable. As for (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-methacryloxyethyl propylene oxide, 3-methyl-3-propenyloxyethyl propylene oxide, 3-ethyl-3-methacryloxyethyl propylene oxide, 3-ethyl-3-propenyloxyethyl ring Propane and so on.

In the case of (b3), a tetrahydrofuranyl group and a (meth) propyl group The alkenoyloxy monomer is more preferred. 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 terms of (b), from the viewpoint of further improving the reliability of the obtained color filter, such as heat resistance and chemical resistance, (b1) is preferred. Furthermore, (b1-2) is more preferable from the viewpoint of excellent storage stability of the colored photosensitive resin composition.

As for (c), for example, methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, secondary butyl (meth) acrylate, (meth) Tertiary butyl acrylate, 2-ethylhexyl (meth) acrylate, dodecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, (meth) acrylic acid Cyclopentyl, cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, tricyclo [5.2.1.0 ^2.6 ] decane-8-ester (in the technical field The common name is "dicyclopentyl (meth) acrylate". Also, it is sometimes called "tricyclodecyl (meth) acrylate"), tricyclo (meth) acrylate [5.2.1.0 ^2.6 ] decene -8-ester (In the technical field, the common name is "dicyclopentenyl (meth) acrylate".), Dicyclopentyloxyethyl (meth) acrylate, isoamyl (meth) acrylate , Permantane (meth) acrylate, allyl (meth) acrylate, propargyl (meth) acrylate, phenyl (meth) acrylate, naphthyl (meth) acrylate, (meth) acrylic acid (Meth) acrylates such as benzyl esters; 2-hydroxy (meth) acrylate Esters, (meth) acrylates containing hydroxyl groups such as 2-hydroxypropyl (meth) acrylate; dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, diethyl iconate ; 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 butoxycarbonyl bicyclo [2.2.1] hept-2-ene, 5-cyclohexyloxycarbonyl bicyclo [2.2.1] hept-2-ene, 5-phenoxycarbonyl bicyclo [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-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, 3-maleimide N-succinimide amine benzoate, N-succinimide 4-maleimide butyrate, N-succinimide 6-maleimide hexanoate, 3-maleimide N- (9-acridinyl) maleimide (N- (9-acridinyl) maleimide) and other dicarbonyl sulfonimide derivatives; styrene, α -Methylstyrene, m-methylstyrene, p-methylstyrene, vinyl toluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinyl chloride, propylene Amidoamine, methacrylamidine, vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, and the like.

Among these, from the viewpoint of copolymerization reactivity and heat resistance, styrene, vinyltoluene, benzyl (meth) acrylate, and tricyclic (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 desirable.

Resin [K1], the ratio derived from the individual structural units, among the total structural units constituting the resin [K1], is 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%. 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 a colored patterned coating film is formed, and the solvent resistance of the obtained color filter are Excellent tendency.

Resin [K1], for example, refer to the method described in the document "Experimental Methods for Polymer Synthesis" (Otsu Takayuki Publishing Co., Ltd., First Edition of Chemical Engineering, First Edition, March 1, 1972) and the document Manufactured by the cited reference.

Specific examples include putting a predetermined amount of (a) and (b), a polymerization initiator, a solvent, and the like into a reaction container. For example, by replacing oxygen with nitrogen to form a deoxidizing environment, heating and stirring while Method of insulation. At this time, the polymerization initiator and solvent used here are not particularly limited, and polymerization initiators and solvents commonly used in the art can be used. E.g, Examples of the polymerization initiator include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis (2,4-dimethylvaleronitrile), etc.) and organic compounds. The oxide (such as benzamyl peroxide) may be any solvent as long as it can dissolve each monomer, and examples thereof include the solvent (E) described later as the solvent for the colored photosensitive resin composition of the present invention.

The obtained copolymer may be used as it is after the reaction, may be a concentrated or diluted solution, or may be used as a solid (powder) by a method such as reprecipitation. In particular, when the solvent contained in the colored photosensitive resin composition of the present invention is used 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, which can simplify the process of the present invention. The manufacturing process of a colored photosensitive resin composition.

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

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

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

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

For the resin [K4], after obtaining the copolymer of (a) and (c), the cyclic ether having 2 to 4 carbon atoms in (b) and the carboxylic acid and / or carboxylic acid in (a) can be obtained. It is produced by addition of acid anhydride.

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

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

After the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced with nitrogen, and the reaction catalyst of (b), a carboxylic acid or a carboxylic acid anhydride and a cyclic ether (for example, Such as tris (dimethylaminomethyl) phenol, etc.), and polymerization inhibitors (such as hydroquinone, etc.) are put into a flask, and the resin can be produced by reacting at 60 to 130 ° C for 1 to 10 hours [K4] .

The amount of (b) used is preferably from 5 to 80 mols, more preferably from 10 to 75 mols, relative to (a) 100 mols. Within this range, there is a balance between storage stability of the colored photosensitive resin composition, developability when forming a patterned coating film, and balance of solvent resistance, heat resistance, mechanical strength, and sensitivity of the obtained patterned coating film. The tendency to become good. Since the cyclic ether has high reactivity and unreacted (b) does not easily remain, (b) used for the resin [K4] is preferably (b1), and more preferably (b1-1).

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

The reaction conditions such as the filling method, the reaction temperature, and the time can be appropriately adjusted in consideration of production equipment and the amount of heat generated by polymerization. Also, similar to the polymerization conditions, it is possible to appropriately adjust the charging method and reaction temperature in consideration of production equipment, heat generation due to polymerization, and the like.

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

The ratio of the structural units derived from (b) and (c) is The total number of moles of the entire structural unit of the polymer is derived from the structural unit derived from (b): 5 to 95 mole%. The structural unit derived from (c): 5 to 95 mole%. (b) Structural unit: 10 to 90 mol% Structural unit derived from (c): 10 to 90 mol% is more preferable.

Furthermore, under the same conditions as in the method for producing the resin [K4], the cyclic ether derived from (b) which is contained in the copolymer of (b) and (c), and the carboxylic acid or The carboxylic anhydride reacts to obtain the resin [K5].

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

The resin [K6] is a resin in which the resin [K5] is further reacted with a carboxylic anhydride.

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

As for the carboxylic anhydride, 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 anhydrous, etc. The use amount of the carboxylic acid anhydride is preferably 0.5 to 1 mole per 1 mole of the use amount of (a).

Specific examples of the resin (B) include 3,4-epoxycyclohexyl methyl (meth) acrylate / (meth) acrylic copolymer and (meth) acrylic 3,4-epoxy Tricyclic [5.2.1.0 ^2.6 ] resins such as decyl ester / (meth) acrylic copolymer [K1]; glycidyl (meth) acrylate / benzyl (meth) acrylate / (meth) acrylic acid copolymer , Glycidyl (meth) acrylate / styrene / (meth) acrylic acid copolymer, 3,4-epoxy tricyclic (meth) acrylic acid [5.2.1.0 ^2.6 ] decyl ester / (meth) acrylic acid / N-cyclohexylmaleimide imine copolymer, 3,4-epoxy tricyclo (meth) acrylate [5.2.1.0 ^2.6 ] decyl / (meth) acrylic acid / vinyltoluene copolymer, 3- Resins such as methyl-3- (meth) acryloxymethyl propylene oxide / (meth) acrylic acid / styrene copolymer [K2]; benzyl (meth) acrylate / (meth) acrylic acid copolymer , Styrene / (meth) acrylic copolymer, benzyl (meth) acrylate / tricyclodecyl (meth) acrylate / (meth) acrylic copolymer and other resins [K3]; benzyl (meth) acrylate Ester ((meth) acrylic acid copolymer) Tricyclodecyl ester / styrene / (meth) acrylic acid copolymer added with glycidyl (meth) acrylate resin, tricyclodecyl (meth) acrylate / benzyl (meth) acrylate / (formaldehyde) (Meth) acrylic copolymer copolymerized with resins such as epoxy (meth) acrylic acid ester [K4]; Tricyclodecyl (meth) acrylate / glycidyl (meth) acrylate copolymer and ( (Meth) acrylic acid-reactive resins, resins such as tricyclodecyl (meth) acrylate / styrene / glycidyl (meth) acrylate reacted with (meth) acrylic acid resins [K5]; Resin [K6] and the like, such as a resin in which a copolymer of tricyclodecyl (meth) acrylate / glycidyl (meth) acrylate reacts with (meth) acrylic acid and tetrahydrophthalic anhydride.

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 resin [K3]. When these resins are used, the colored photosensitive resin composition has excellent developability.

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

The polystyrene equivalent weight average molecular weight of the resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and even more preferably 5,000 to 30,000. When the molecular weight is in the aforementioned range, the coating film hardness is increased, and the residual film ratio is also high. The unexposed portion has good solubility in the developing solution, and the resolution of the colored patterned coating film tends to increase.

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

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

The content of the resin (B) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and still more preferably 17 to 55% by mass with respect to the total solid content. When the content of the resin (B) is within the aforementioned range, a colored patterned coating film can be formed, and the resolution and the residual film rate of the colored patterned coating film tend to increase.

<Polymerizable compound (C)>

The polymerizable compound (C) is a compound that can be polymerized by living radicals and / or acids generated from the polymerization initiator (D), and examples thereof include polymerizable compounds The ethylenically unsaturated compound and the like are 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 tri (meth) acrylate, neopentaerythritol tri (meth) acrylate, neopentaerythritol tetra (meth) acrylate, Dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tripentaerythritol octa (meth) acrylate, trinepentaerythritol (meth) acrylate Esters, tetra-pentaerythritol deca (meth) acrylate, tetra-pentaerythritol nine (meth) acrylate, tris (2- (meth) acrylfluorenyloxyethyl) isocyanate, Glycol modified neopentaerythritol tetra (meth) acrylate, ethylene glycol modified dipentaerythritol hexa (meth) acrylate, propylene glycol modified neopentaerythritol tetra (meth) acrylate, Propylene glycol modified dipentaerythritol hexa (meth) acrylate, caprolactone modified neopentaerythritol tetra (meth) acrylate, caprolactone modified dipentaerythritol hexa (meth) acrylate Wait.

Among them, dinepentaerythritol penta (meth) acrylate and dinepentaerythritol hexa (meth) acrylate are particularly preferred.

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

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

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, and more preferably The ideal is 35:65 to 80:20, and even more preferably 50:50 to 75:25, and particularly preferably 55:45 to 70:30.

When the content of the polymerizable compound (C) is within the above range, the residual film rate when the colored patterned coating film is formed 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 generates living radicals, acids, and the like by the action of light or heat, and known polymerization initiators can be used.

As for the polymerization initiator (D), an alkylphenone compound may be mentioned. Compounds, fluorenylphosphine oxide compounds, O-fluorenyl oxime compounds, biimidazole compounds, and the like.

The O-fluorenyl oxime compound is a compound having a partial structure represented by formula (d1). In the following, * indicates a bond key.

Examples of the O-fluorenyl oxime compound include N-benzylfluorenyloxy-1- (4-phenylthiophenyl) butane-1-one-2-imine, and N-benzyl Fluorenyloxy-1- (4-phenylthiophenyl) octane-1-one-2-imine, N-benzylfluorenyloxy-1- (4-phenylthiophenyl)- 3-cyclopentylpropane-1-one-2-imine, N-ethoxyl-1- [9-ethyl-6- (2-methylbenzylfluorenyl) -9H-carbazole-3- Alkyl] ethane-1-imine, N-ethoxy-1--1- [9-ethyl-6- {2-methyl-4- (3,3-dimethyl-2,4-dioxo Heterocyclopentylmethyloxy) benzylfluorenyl} -9H-carbazol-3-yl] ethane-1-imine, N- Acetyloxy-1- [9-ethyl-6- (2-methylbenzylfluorenyl) -9H-carbazole) -3-yl] -3-cyclopentylpropane-1-imine, N- Benzylfluorenyloxy-1- [9-ethyl-6- (2-methylbenzylfluorenyl) -9H-carbazol-3-yl] -3-cyclopentylpropane-1-one-2-ylidene Amine, etc. Commercial products such as Irgacure OXE01, OXE02 (above, manufactured by BASF), and N-1919 (made by ADEKA) can also be used.

Among them, the O-fluorenyl oxime compound consists of N-benzylfluorenyloxy-1- (4-phenylthiophenyl) butane-1-one-2-imine, N-benzylfluorenyloxy -1- (4-phenylthiophenyl) octane-1-one-2-imine and N-benzylfluorenyloxy-1- (4-phenylthiophenyl) -3-cyclopentane At least one selected from the group consisting of propylpropane-1.-one-2-imine is preferred, and N-benzylfluorenyloxy-1- (4-phenylthiophenyl) octane-1- Keto-2-imines are more preferred.

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

Examples of the compound having a partial structure represented by the formula (d2) include 2-methyl-2- (N-morpholinyl) -1- (4-methylthiophenyl) propane-1- Ketone, 2-dimethylamino-1- (4- (N-morpholinyl) phenyl) -2-benzylbutane-1-one, 2- (dimethylamino) -2- [ (4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] butane-1-one and the like. Commercial products such as Irgacure 369, 907, and 379 (above, manufactured by BASF) can also be used.

For a compound having a partial structure represented by formula (d3), for example, Examples include 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-hydroxy-2-methyl-1- (4- (2-hydroxyethoxy) phenyl] propane-1- Ketone, 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1- (4-isopropenylphenyl) propane-1-one oligomer, α, α-diethoxybenzene Ethyl ketone, benzyl dimethyl ketal, etc.

From the viewpoint of sensitivity, a benzophenone compound is preferably a compound having a partial structure represented by formula (d2).

The aforementioned biimidazole compound is, for example, a compound represented by 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 phenyl, tolyl, xylyl, ethylphenyl, and naphthyl, and phenyl is preferred.

Examples of the substituent include a halogen atom, an alkoxy group having 1 to 4 carbon atoms, and the like. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like, and a chlorine atom is preferable. Examples of the alkoxy group having 1 to 4 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, and a butoxy group, 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 the 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 particularly preferred.

Just three For compounds, for example, 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-tris , 2,4-bis (trichloromethyl) -6- (4-methoxynaphthyl) -1,3,5-tris , 2,4-bis (trichloromethyl) -6-sunfloweryl-1,3,5-tri , 2,4-bis (trichloromethyl) -6- (4-methoxystyryl) -1,3,5-tris , 2,4-bis (trichloromethyl) -6- [2- (5-methylfuran-2-yl) vinyl] -1,3,5-tris , 2,4-bis (trichloromethyl) -6- [2- (furan-2-yl) vinyl] -1,3,5-tris , 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino-2-methylphenyl) vinyl] -1,3,5-tris , 2,4-bis (trichloromethyl) -6- [2- (3,4-dimethoxyphenyl) vinyl) -1,3,5-tri Wait.

Examples of the fluorenylphosphine oxide compound include 2,4,6-trimethylbenzylfluorenyldiphenylphosphine oxide and the like.

In terms of the polymerization initiator (D), benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether and other benzoin compounds; benzophenone, o-benzyl benzoate Methyl ester, 4-phenylbenzophenone, 4-benzylfluorenyl-4'-methyldiphenyl sulfide, 3,3 ', 4,4'-tetrakis (tertiary butylcarbonyl) benzophenone 2,2,4,6-trimethylbenzophenone and other benzophenone compounds; 9,10-phenanthrenequinone, 2-ethylanthraquinone, camphorquinone and other quinone compounds; 10-butyl-2-chloroacridone , Benzil, methyl phenylglyoxylalte, titanocene compounds, and the like. These are preferably used in combination with a polymerization initiator (D1) (especially amines) described later.

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

The content of the polymerization initiator (D) is preferably 1 to 50 parts by mass, more preferably 10 to 45 parts by mass based on 100 parts by mass of the total amount 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 or a sensitizer for promoting the polymerization of a polymerizable compound that is polymerized by a polymerization initiator. When a polymerization initiator (D1) is contained, it can be used together with a polymerization initiator (D) normally.

Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

Examples of the aforementioned amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, 4-diamine Methylamino Benzoate Isoamyl Ester, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N, N-dimethyl-p-toluidine, 4,4'-bis (dimethylformamide Methylamino) benzophenone (commonly known as Michler's ketone), 4,4'-bis (diethylamino) benzophenone, 4,4'-bis (ethylmethylamino) Among them, benzophenone and the like are particularly preferred. Commercial products such as EAB-F (Hodogaya Chemical Industry Co., Ltd.) can also be used.

Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethylanthracene, 2-ethyl -9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, 2-ethyl-9,10-dibutoxyanthracene and the like.

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

Examples of the carboxylic acid compound include phenylthioglycolic acid, methylphenylthioglycolic acid, ethylphenylthioglycolic acid, methylethylphenylthioglycolic acid, and dimethylphenylthioglycolic acid. , Methoxyphenylthioglycolic acid, dimethoxyphenylthioglycolic acid, chlorophenylthioglycolic acid, dichlorophenylthioglycolic acid, N-phenylglycine, phenoxyacetic acid, naphthyl Thioacetic acid, N-naphthylglycine, naphthyloxyacetic acid, etc.

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

<Thiol compound (T)>

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

For compounds having one -SH in the molecule, for example, 2-thio Azole, 2-thiothiazole, 2-thiobenzimidazole, 2-thiobenzothiazole, 2-thiobenzo Azole, 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-tetrahydropyrimidine-2-thiol, 4,5-diphenylpyrazole- 2-thiol, 2-thiopyrazole, 2-thio-1-methylpyrazole, 4-amino-3-hydrazino-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-thio 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- 2-sulfanyl-5-thiazolido ne), 2-sulfanyl thiazoline, 2-sulfanyl-4 (3H) -quinazolinone, 1-phenyl-1H- Tetrazol-5-thiol, 2-quinolinethiol, 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-thionaphthoimidazole , 2-thionaphtho Azole, 3-thio-1,2,4-triazole, 4-amino-6-thiopyrazolo [2,4-d] pyridine, 2-amino-6-purinethiol, 6- Thiopurines, 4-thio-1H-pyrazolo [2,4-d] pyrimidines and the like.

Examples of compounds having two or more -SH in the molecule include hexanedithiol, decanedithiol, 1,4-bis (methylthio) benzene, and butanediol bis (3-thio Propionate), butanediol bis (3-thioacetate), ethylene glycol bis (3-thioacetate), trimethylolpropane tris (3-thioacetate) , Butanediol bis (3-thiopropionate), trimethylolpropane tri (3-thiopropionate), trimethylolpropane tri (3-thioacetate), neopentyl Tetraol tetra (3-thiopropionate), neopentaerythritol tetra (3-thioacetate), trihydroxyethyltris (3-thiopropionate), neopentyl tetraol tetra (3 -Thiobutyrate), 1,4-bis (3-thiobutoxy) butane and the like.

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

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

<Solvent (E)>

The solvent (E) is not particularly limited, and solvents commonly used in the art can be used. For example, ester solvents (solvents containing -COO- and -O-free), ether solvents (solvents containing -O- and -COO-free), and ether ester solvents (containing- COO- and -O- solvents), ketone solvents (solvents containing -CO-, -COO-free solvents), alcohol solvents (containing OH in the molecule, -O-, -CO- free) -COO- solvents), aromatic hydrocarbon solvents, amidine solvents, dimethyl sulfene and the like.

As the ester solvent, methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate Esters, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl ethyl acetate, ethyl ethyl acetate, Cyclohexyl acetate, γ-butyrolactone, etc.

Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, and diethylene glycol. 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-butane Alcohol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-bis 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.

As the ether ester solvent, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, 3-methoxypropyl Methyl ester, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, 2-methoxypropionate Ethyl acetate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, 2 -Ethyl ethoxy-2-methylpropanoate, 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.

Examples of the ketone solvent include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, and 4-methyl-2. -Pentanone, cyclopentanone, cyclohexanone, isophorone, etc.

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

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

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

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

Among the solvents described above, an organic solvent having a boiling point of 1 atmosphere and a temperature of 120 ° C. or higher and 180 ° C. or lower is preferable from the viewpoints of coating properties and drying properties. Among them, propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, ethylene glycol monobutyl ether, and 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 are ideal, and propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethylene glycol monobutyl ether, dipropylene glycol methyl ether acetate, ethyl lactate Esters, 3-methoxybutyl acetate, 3-methoxy-1-butanol and ethyl 3-ethoxypropionate are more preferred.

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

When the content of the solvent (E) is in the aforementioned range, the flatness at the time of coating is good, and the color density is sufficient when forming a color filter, so the display characteristics tend to be good.

<Leveling agent (F)>

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

Examples of the polysiloxane-based surfactant include a surfactant having a siloxane bond in the molecule. Specifically, Toray Silicone DC3PA is the same as SH7PA, the same as DC11PA, the same as SH21PA, the same as SH28PA, the same as SH29PA, the same as SH30PA, and the same as SH8400 (trade name; Toray DOW Corning (stock)); KP321, KP322 , KP323, KP324, KP326, KP340, KP341 (made by Shin-Etsu Chemical Industry Co., Ltd.); TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452 and TSF4460 (made by Momentive Performance Materials Japan) and so on.

Examples of the fluorine-based surfactant include a surfactant having a fluorocarbon chain in the molecule. Specific examples include Fluorad (registered trademark) FC430, the same as FC431 (Sumitomo 3M (shares)); Megafac (registered trademark) F142D, the same as F171, the same as F172, the same as F173, the same as F177, the same as F183, the same as F554, R30, same as RS-718-K (DIC (shares) system); Eftop (registered trademark) EF301, the same as EF303, the same as EF351, the same as EF352 (Mitsubishi Materials Electronics Co., Ltd.); Surflon (registered trademark) S381, the same as S382, the same SC101, the same as SC105 (the Asahi Glass (stock)) Same as E5844 (made by Daikin Fine Chemicals Research Institute).

Examples of the polysiloxane-based surfactant having a fluorine atom include a surfactant having a siloxane bond and a fluorocarbon chain in the molecule. Specific examples include Megafac (registered trademark) R08, the same as BL20, the same as F475, the same as F477, and the same as F443 (the DIC system).

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 with respect to the total amount of the colored photosensitive resin composition. 0.05 mass% or less. When the content of the leveling agent (F) is within the aforementioned range, the flatness of the color filter can be made good.

<Adhesion promoter (G)>

Examples of the adhesion promoter (G) include ethylene trimethoxysilane, ethylene triethoxysilane, ethylene tri (2-methoxyethoxy) silane, and 3-glycidoxypropane. Trimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyl Didiethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-thiopropyltrimethoxysilane, 3-isocyanatepropyltriethoxysilane, N-2 -(Aminoethyl) -3-aminopropylmethyldimethoxysilane, N-2- (aminoethyl) -3-aminopropylmethyldiethyl Oxysilane, N-2- (aminoethyl) -3-aminopropyltrimethoxysilane, N-2- (aminoethyl) -3-aminopropylmethyldiethoxysilane , 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, N-phenyl-3-aminopropyl Triethoxysilane and the like.

The content of the adhesion promoter (G) is preferably 0.1% by mass or more and 5% by mass or less, and preferably 0.2% by mass or more and 2% by mass or less with respect to the total solid content. When the content of the adhesion promoter (G) is within the aforementioned range, adhesion to the substrate can be made good.

<Other ingredients>

The colored photosensitive resin composition of the present invention may contain fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents, etc., as known additives in the technical field, as needed.

<Manufacturing method of colored photosensitive resin composition>

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

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

The mixed colored photosensitive resin composition is preferably filtered using a filter membrane having a pore size of about 0.1 to 10 μm.

<Manufacturing Method of Color Filter>

Examples of the method for producing a colored patterned coating film from the colored photosensitive resin composition of the present invention include a lithography method, an inkjet method, and a printing method. Among them, a lithographic etching method is preferable. The lithographic etching method is a method in which the colored photosensitive resin composition is coated on a substrate and dried to form a colored composition layer, and the colored composition layer is exposed and developed through a photomask. In the lithographic etching method, a colored coating film of a cured product of the coloring composition layer can be formed without using a mask and / or without developing during exposure. The colored patterned coating film or colored coating film thus formed is the color filter of the present invention.

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

For the substrate, glass plates such as quartz glass, borosilicate glass, aluminum silicate glass, and soda-lime glass coated with silicon oxide can be used; polycarbonate, polymethyl methacrylate, Resin plates such as polyethylene terephthalate; silicon, on which substrates such as aluminum, silver, and silver / copper / palladium alloy films are formed. On these substrates, other color filter layers, resin layers, transistors, circuits, etc. can be formed.

The formation of each color pixel by the lithographic etching method can be performed by a known or conventional apparatus and conditions. For example, it can be produced as follows.

First, a colored photosensitive resin composition is coated on a substrate, and volatile components such as solvents are removed and dried by heating (pre-baking) and / or drying under reduced pressure to obtain a smooth colored composition layer.

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

The temperature for heating and drying is preferably 30 to 120 ° C, and more preferably 50 to 110 ° C. The heating time is preferably 10 seconds to 60 minutes, and more preferably 30 seconds to 30 minutes.

It is preferable to perform the drying under reduced pressure at a pressure in the range of 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 colored patterned coating film for the purpose. The pattern on this photomask is not particularly limited, and a pattern suitable for the purpose can be used.

As the light source for exposure, a light source that generates light having a wavelength of 250 to 450 nm is desirable. For example, it is possible to use light that is below 350 nm to cut the filter in this wavelength range, or use light at about 436 nm, 408 nm, and 365 nm to take out band-pass filters in these wavelength regions. ) And selectively remove.

Specific examples include a mercury lamp, a light-emitting diode, a metal halide lamp, and a halogen lamp.

In order to uniformly radiate parallel light to the entire exposure surface, or to adjust the position of the substrate on which the photomask and the coloring composition layer are formed correctly, a photomask is used. Exposure devices such as aligners and steppers are ideal.

A colored patterning coating film is formed on the substrate by developing the colored composition layer after exposure in contact with a developing solution. The unexposed portion of the colored composition layer is dissolved in a developing solution and removed through development.

As the developing solution, for example, an aqueous solution of a basic compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, tetramethylammonium hydroxide, etc. is preferable. The concentration in the aqueous solution of these basic compounds is preferably 0.01 to 10% by mass, and more preferably 0.03 to 5% by mass. Furthermore, the developing solution may contain a surfactant.

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

After development, washing with water is preferred.

Furthermore, it is desirable to perform the post-baking by applying the obtained colored patterned coating film. The post-baking temperature is preferably 150 to 250 ° C, and more preferably 160 to 235 ° C. The post-baking time is preferably 1 to 120 minutes, and more preferably 10 to 60 minutes.

If the colored photosensitive resin composition according to the present invention has less generation of residues or residual films, a color filter with few defects can be produced. This color filter is useful as a color filter used in display devices (for example, liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state image sensors.

Examples

Examples are given next to explain the present invention more specifically. In the example, "%" and "part" indicate mass% and mass part unless otherwise specified.

Synthesis Example 1

In a flask equipped with a stirrer, a thermometer, a reflux condenser, and a dropping funnel, nitrogen gas was flowed at 0.02 L / min to form a nitrogen environment. 257 parts by mass of propylene glycol monomethyl ether acetate was charged, and heated to 70 with stirring. ℃. Next, 8 parts of acrylic acid, 70 parts of N-cyclohexylmaleimide, 3,4-epoxytricyclo [5.2.1.0 ^2.6 ] decane-8-ester of acrylic acid, and 3,4-epoxy of acrylic acid were added. 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) was dissolved in 140 parts by mass of propylene glycol monomethyl ether acetate to prepare a solution. This solution was dropped into a flask held at 70 ° C. over 4 hours using a dropping funnel.

On the other hand, a solution in which 15 parts by mass of a polymerization initiator 2,2'-azobis (2,4-dimethylvaleronitrile) was dissolved in 225 parts by mass of propylene glycol monomethyl ether acetate was used. It took 4 hours for the dropping funnel to drip into the flask. After the dripping of the solution of the polymerization initiator was completed, the solution 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 units.

Synthesis Example 2

In a flask equipped with a reflux condenser, a dropping funnel, and a stirrer, an appropriate amount of nitrogen was passed to replace the nitrogen atmosphere, and 371 parts of propylene glycol monomethyl ether acetate was charged, and 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 of acrylic acid were prepared. -225 parts of a mixture of esters (containing a molar ratio of 50:50), 81 parts of vinyl toluene (isomer mixture), and a mixed solution prepared by dissolving in 80 parts of propylene glycol monomethyl ether acetate. 4 hours into the flask.

On the other hand, a solution in which 30 parts of a polymerization initiator 2,2-azobis (2,4-dimethylvaleronitrile) was dissolved in 160 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. . After the addition of the initiator solution was completed, the solution was kept at 85 ° C. for 4 hours, and then cooled to room temperature to obtain a copolymer solution. This copolymer was referred to as resin B2. The solid content of the resin B2 solution was 37.5%, and the viscosity measured by a 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 units.

Synthesis Example 3

200 parts of propylene glycol monomethyl ether acetate was introduced into a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel, and a gas introduction tube. Thereafter, nitrogen was introduced into the flask through a gas introduction tube, and the environment in 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 A mixture of 213 parts of propylene glycol monomethyl ether acetate was dropped into the flask over a 2 hour period using a dropping funnel, and the mixture was stirred at 100 ° C. for 5 hours after the dropping was completed. After the dripping of the solution of the polymerization initiator was completed, the solution was kept at 70 ° C. for 4 hours, and then cooled to room temperature to obtain a resin B3 solution having a solid content of 33.6%. 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 units.

Synthesis Example 4

200 parts of propylene glycol monomethyl ether acetate was introduced into a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel, and a gas introduction tube. Thereafter, nitrogen was introduced into the flask through a gas introduction tube, and the environment in 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 tricyclic [5.2.1.0 ^2.6 ] decyl ester, 42 parts of acrylic acid, 5.2 parts of azobisisobutyronitrile, and propylene glycol A mixture of 213 parts of monomethyl ether acetate was dropped into the flask over a period of 2 hours using a dropping funnel, and after the dropping was completed, the mixture was stirred at 100 ° C. for 5 hours. After the dropping of the solution of the polymerization initiator was completed, the solution was kept at 70 ° C. for 4 hours, and then cooled to room temperature to obtain a resin B4 solution having a solid content of 34.1%. 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 units.

The polystyrene equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by the GPC method under the following conditions.

Device: HLC-8120GPC (made by Tosoh Corporation)

Column: TSK-GELG2000HXL

Column temperature: 40 ℃

Solvent: THF

Flow rate: 1.0ml / min

Tested liquid solid content concentration: 0.001 to 0.01% by mass

Injection volume: 50 μL

Detector: RI

Calibration Standards: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500

(Tosoh (shares) system)

The polystyrene-equivalent weight average molecular weight and the number average molecular weight ratio (Mw / Mn) were used as the molecular weight distribution.

[Preparation of pigment dispersion liquid A1]

78.3 parts of propylene glycol monomethyl ether acetate

These were mixed and the pigment was fully dispersed using a bead mill to obtain a pigment dispersion liquid A1.

[Preparation of pigment dispersion liquid A2]

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

[Preparation of pigment dispersion liquid A3]

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

[Preparation of pigment dispersion liquid A4]

These were mixed and the pigment was fully dispersed using a bead mill to obtain a pigment dispersion liquid A4.

(Preparation of pigment dispersion liquid A5)

These were mixed, and the pigment was fully dispersed using a bead mill to obtain a pigment dispersion liquid A5.

Examples 1 to 8 and Comparative Example 1

[Preparation of colored photosensitive resin composition]

The components described in Table 1 were mixed to obtain a colored photosensitive resin composition.

In Table 1, the column "resin (B)" indicates the content (parts) in terms of solid content.

The colorant (A) is prepared in advance as pigment dispersion liquids A1 to A5, and is used for mixing. The "colorant (A)" column in Table 1 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 dispersant contained in the pigment dispersion liquid used.

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

In Table 1, each component is as follows.

Colorant (A): A1: C.I. Pigment Green 58 (Pigment 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 and 70 parts of benzyl methacrylate, and then adding 9 parts of epoxypropyl methacrylate in the presence of a triethanolamine catalyst (weight Average molecular weight: 1.2 × 10 ⁴ , acid value in terms of solid content: 80mg-KOH / g)

Polymerizable compound (C): C1: dipentaerythritol hexaacrylate (KAYARAD (registered trademark); DPHA: made by Nippon Kayaku Co., Ltd.)

Polymerizable compound (C): C2: dineopentaerythritol pentaacrylate

Polymerization initiator (D): D1: N-benzylfluorenyloxy-1- (4-phenylthiophenyl) octan-1-one-2-imine (Irgacure (registered trademark) OXE01; BASF Company; O-fluorenyl oxime compound)

Polymerization initiator (D): D2: 2-methyl-2- (N-morpholinyl) -1- (4-methylthiophenyl) propane-1-one (Irgacure (registered trademark) 907; (Manufactured by BASF; benzonone 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: manufactured by Sumitomo Chemical Co., Ltd .: compound represented by the following formula)

Adhesion promoter (G): D1b: 3-Methacryloxypropyltrimethoxysilane (KBM-503: Shin-Etsu Chemical Industry 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 silicone oil (manufactured by Toray Dow Corning Co., Ltd .; SH8400)

[Production of patterned coating film]

The colored photosensitive resin composition was applied on a 2-inch-square glass substrate (Eagle XG; manufactured by Corning) by a spin coating method, and then prebaked at 100 ° C for 3 minutes to form a colored composition layer. After leaving to cool, the distance 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) was used at 30 mJ / cm in an atmospheric environment. An exposure amount of ² (based on 365 nm) was irradiated with light. As the photomask, a photomask having a line-and-space pattern of 50 μm was used. After the light was irradiated, the above coating film was dipped in an aqueous developing solution containing 0.12% of a non-ionic surfactant and 2% of sodium carbonate at 24 ° C for 60 seconds for development. 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 with an optical microscope, and when no residue or a residual film was not observed in the unexposed portion, it was regarded as ○, and when viewed, it was ×. The results are shown in Table 2.

[Adhesion evaluation]

The colored patterned coating film was observed with an optical microscope. When no peeling was observed, it was regarded as ○. When a part of the colored patterned coating film was observed, it was regarded as △. When the colored patterned coating film was completely peeled, it was regarded as ×. . The results are shown in Table 2.

[Measurement of film thickness]

About the obtained colored patterning coating film, the film thickness was measured using the film thickness measuring device (DEKTAK3; made by Japan Vacuum Technology Co., Ltd.). The results are shown in Table 2.

[Chroma evaluation]

With respect to the obtained colored patterned coating film, a spectrometer (OSP-SP-200; manufactured by Olympus Co., Ltd.) was used to measure spectrometry, and a characteristic function of the C light source was used to measure the xy chromaticity coordinates (x, y) and tristimulus value Y. A larger Y value indicates higher brightness. The results are shown in Table 2.

According to the colored photosensitive resin composition of the present invention, excellent developability can be obtained when a colored patterned coating film is formed.

Claims (5)

A colored photosensitive resin composition containing a colorant, a resin, a polymerizable compound, a polymerization initiator, and a solvent. The colorant contains CI Pigment Green 58, a yellow pigment, and a blue pigment, a red pigment, a purple pigment, 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. The aforementioned pigments are composed of blue, red, purple, and orange pigments. The content rate of at least one selected by the group is 0.1 to 5% by mass based on the total amount of the colorant. The colored photosensitive resin composition according to item 1 of the scope of patent application, wherein the resin is an addition polymerization of at least one structural unit selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic anhydride. Thing. The colored photosensitive resin composition according to item 1 or item 2 of the patent application scope, wherein the ratio of the content of the resin to the content of the polymerizable compound is 20:80 to 80:20 on a mass basis. A color filter is formed of the colored photosensitive resin composition according to any one of claims 1 to 3 of the scope of patent application. A display device includes the color filter described in item 4 of the scope of patent application.