TW201232174A - Colored photosensitive resin composition - Google Patents

Abstract

A colored photo-sensitive resin composition, a pattern based on the composition, a color filter based on the composition, and a method for manufacturing the composition are provided to improve the solvent resistance characteristic of the composition although a high temperature-based baking process is omitted. A colored photo-sensitive resin composition includes a coloring agent, copolymer, resin, polymeric compound, polymerization initiator, and a solvent. Ethylenically unsaturated bond is arranged at the side chain of the resin. The copolymer includes structural units derived from at least one selected from unsaturated carboxylic acid and unsaturated carboxylic anhydride and derived from C2 to C4 cyclic ether and monomer with ethylenically unsaturated bond.

Description

201232174 VI. [Technical Field] The present invention relates to a color-developing photosensitive resin composition which is preferable in forming a color image of a color filter used for a liquid crystal display element or a solid-state image sensor. [Prior Art] A color filter used for a display device such as a liquid crystal display panel, an electroluminescence panel, or an electric display panel is manufactured by using a colored photosensitive resin composition. It is known that the coloring photosensitive resin composition contains a pigment, a resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent, and the resin is a composition of a copolymer of methacrylic acid and an unsaturated compound having an oxiranyl group. (Patent Document 1). [PRIOR ART DOCUMENT] [Patent Document 1] [Patent Document 1] JP-A No. 20-7-3 3 3 847 SUMMARY OF THE INVENTION PROBLEMS TO BE SOLVED BY THE INVENTION When a pattern is formed using the colored photosensitive resin composition, The resolution of the pattern is not very satisfactory. Means to solve the invention

-5- 201232174 The present invention provides the following [1] to [8]. [1] A colored photosensitive resin composition containing (A), (B1), (B2), (C), (D) and (E): (A) a colorant; (B1) containing a color selected from a copolymer of at least one structural unit of a group of a saturated carboxylic acid and an unsaturated carboxylic anhydride, and a structural unit derived from a monomer having a cyclic ether having 2 to 4 carbon atoms and an ethylenically unsaturated bond (but on the side) There is no ethylenically unsaturated bond in the chain; (B2) a resin having an ethylenically unsaturated bond in the side chain; (C) a polymerizable compound; (D) a polymerization initiator; (E) a solvent. [2] (B2) is a colored photosensitive resin composition according to the above [1] which is obtained by copolymerizing the copolymer obtained in the following (a) and (c) with the resin obtained by the reaction of (b): (a) : at least one selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides; (b): a monomer having a cyclic ether having 2 to 4 carbon atoms and an ethylenically unsaturated bond; (c): having The monomer of the unsaturated bond copolymerized with (a) and (b) (2-2) (B2) is further obtained by copolymerizing the copolymers obtained by the following (a) and (c) with (b) The coloring photosensitive resin composition of the above-mentioned [1] of the resin obtained by the reaction: -6-201232174 (a): at least one selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides; (b): a monomer having an oxirane group and an ethylenically unsaturated bond; (c): a monomer having an unsaturated bond copolymerizable with (a) and (b). [3] The content of (B1) is (B1) The color-sensitive photosensitive resin composition of the above [1] or [2], which is 10% by mass or more and 95% by mass or less, in combination with (B2). [4] From the above [1]~ 3 A pattern formed by the colored photosensitive resin composition according to any one of the above [5], wherein the color filter of the pattern of the above [4] is contained. [6] contains the following (1) to (4). (1) A method of applying a colored photosensitive resin composition according to any one of the above [1] to [3] to a substrate to obtain a coating film; (2) a step of obtaining a film after exposure by exposure of a coating film through a mask; (3) a step of obtaining a pattern by developing the film after exposure with an alkali developing solution; (4) The step of obtaining a pattern by baking the pattern by baking. [7] The step (4) is the above [6] of the step of baking at a temperature of 1 20 ° C or lower. [Manufacturing method of the color filter described in the above [1]] The substrate in the step (1) is a method of producing the color filter according to the above [6] or [7] of the plastic substrate. [Effect of the Invention] A coloring photosensitive resin composition can obtain a pattern having excellent resolution. The coloring photosensitive resin composition of the invention contains a coloring agent (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), and a solvent (E), and the resin (B) contains (B1) a copolymer derived from at least one structural unit selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic anhydride, and a structural unit derived from a monomer having a cyclic ether having 2 to 4 carbon atoms and an ethylenically unsaturated bond (There is no ethylenic unsaturated bond in the side chain.) (hereinafter sometimes referred to as "resin (B1)") and (B2) a resin having an ethylenic unsaturated bond in the side chain (hereinafter sometimes referred to as " Resin of Resin (B2)") The colored photosensitive resin composition of the present invention contains a coloring agent (A). Although the pigment and the dye are mentioned as the coloring agent (A), it is preferable to contain a pigment from the viewpoint of heat resistance and light resistance. Examples of the pigment include organic pigments and inorganic pigments, and examples thereof include compounds classified by color index (published by The Society of Dyers and Col〇 Urists). Specific examples of the organic pigments include CI pigment yellow 1, 3, 201232174 12, 13 1 ' 14, 15, 16, 17, 20, 24 '31, 53 '83, 94, 109, 110, 117, 125, 128 ' 13 7 ' 138 , , 148 , 150 , 153 , 154 , 166 , 173 ' 194 > 214 etc . » CI pigment orange 13, 31, 36, 38 ' 40, 42 ' 43 , 59 , 61 , 64 , Orange pigments such as 65, 71, 73; C.I. Pigment red 9 , 97 , 105 , 122 , 123 , 144 , 168 , 176 , 177 ' 180 , 192 , 209 ' 215 , 216 , 254 , 255 ' 264 , 265 and other red pigments » C. , I. Pigment blue 1 5 , 15: 3 , 15: 4 '15: 6, 60 0; CI pigment purple 1, 19, 23, 29, 32, 36 '38, etc. 1 CI pigment green 7, 36 '58 and other green pigments; CI pigment coffee 2 3, 2 5 and other brown pigments; and CI pigment black 1, 7 and other black pigments. Among them, C.I. pigment yellows 138, 139, 150, C 177, 242, 254, C.1. Pigment red purple 23, C.I. pigment blue 1 : 6 and C.I. pigment green 7, 3 6 and 5 8 are preferred. These pigments can be used in combination of two or more kinds. _a-£- 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料Treatment or removal of impurities by organic solvent or water treatment, removal of ionic impurities by ion exchange method, etc., 8 6 , 9 3 139 > 147 yellow pigment ' 51 > 55 149 ' 166 224 , 242 , etc . Purple pigment. I. Pigment red 5 : 3 ' 15 Separate or mixed acidic groups, or by washing by a high-micronization method or the like is preferred. -9- 201232174 Further, it is preferred that the pigment has a uniform particle size. By dispersing the pigment dispersant, it is possible to obtain a dispersion in which the pigment is uniformly dispersed in the solution. As the pigment dispersant, a commercially available surfactant can be used as the surfactant, and examples thereof include polyfluorene-based, fluorine-based, ester-based, daughter-based, anionic-based nonionic, amphoteric, polyester, and poly. An amine olefinic surfactant. As the above surfactant, in addition to polycycloalkyl alkyl ethers, polyethylene oxide alkylphenyl ethers, polyethylene glycol di, sorbitan fatty acid esters, fatty acid modified polyesters, tertiary amine polyurethanes Other than the class, polyethyleneimine, etc., may be given by Shin-Etsu Chemical Co., Ltd., Floren (Kyoei Chemical Co., Ltd., Solsperse (Zeneca), EFKA (CIBA) Aj i sper (Aj iη〇m〇t 〇F i ne - Te chn 〇Cο ·, Inc., manufactured by Inc., etc.) may be used singly or in combination of two or more. When a pigment dispersant is used, the amount is used. The pigment weight is 100% by mass or less, and more preferably 5 to 50% by mass. When the amount of the pigment dispersion used is within the above range, the dispersion of the material in a uniformly dispersed state tends to be obtained. The amount of the solid content of the coloring photosensitive resin is preferably from 5 to 60% by mass, more preferably not more than 5% by mass. When the content of the coloring agent (A) is within the above range, the desired wavelength is obtained. Or color concentration. The solid phase is obtained by removing the components of the solvent from the coloring photosensitive resin composition.] The fraction is divided into cations and propoxyethylated denatured KP (shares) company's two preferred agents. ~45 can be scored, -10- 201232174 The colored photosensitive resin composition of the present invention is a resin containing a resin (B 1 ) (B). The resin (B1) is contained from an unsaturated acid selected from unsaturated and unsaturated. At least one type of carboxylic anhydride group (hereinafter sometimes referred to as "(a)")), a monomer derived from a cyclic ether having a carbon number of 2 to 4, and an ethylenically unsaturated bond (hereinafter sometimes a copolymer of a structural unit called "(b)") (but no ethylenic unsaturated bond in the side chain). The colored photosensitive resin composition has a heat resistance of the resulting pattern by the resin (B 1 ) For example, the resin (B 1 ) is a resin (B1-1): a copolymer obtained by polymerizing (a) and (b), and a resin (B1). -2): Polymerization of (a), (b) and monomer (c) having an unsaturated bond capable of copolymerizing (a) and (b) (below) The copolymer formed by the term "(c)") is preferably (B 1 -1 ) as the resin (B 1 ). Specific examples of (a) include acrylic acid, methacrylic acid, crotonic acid, and hydrazine. - unsaturated monocarboxylic acids such as ethylene benzoic acid, m-ethylene benzoic acid, p-ethylene benzoic acid; maleic acid, fumaric acid, methyl maleic acid, mesaconic acid, itaconic acid, 3-ethylene Tannic acid, 4-vinyl phthalic acid, 3,4,5,6-tetrahydrofurfuric acid, 1,2,3,6-tetrahydrofurfuric acid, dimethyltetrahydrofurfuric acid, 1, 4-cyclohexene Unsaturated dicarboxylic acids such as dicarboxylic acid; methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxyl linkage Ring [2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2"]hept-2 - Alkene 201232174, 5-carboxyl group: 6-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene, etc. Cyclic unsaturated compounds; maleic anhydride, methyl cis-butanic anhydride, itaconic anhydride, 3-vinyl phthalic anhydride, 4-vinyl phthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1, 2,3,6-tetrahydrogen Unsaturated dicarboxylic acid anhydrates such as phthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydrate (norbornene dianhydride) » succinic acid single Unsaturated mono[(meth)propene of a polyvalent carboxylic acid having two or more valences such as [2-(meth) propylene oxiranylethyl] or phthalic acid mono [2-(methyl) propylene methoxyethyl] a decyloxyalkyl ester; an unsaturated acrylate having a hydroxyl group and a carboxyl group in the same molecule, such as α-(hydroxymethyl)acrylic acid. Among them, acrylic acid, methacrylic acid, maleic anhydride, and the like are used from the viewpoint of copolymerization reactivity or alkali solubility. In the present specification, "(meth)acrylic acid" means at least one selected from the group consisting of acrylic acid and methacrylic acid. The meanings of "(meth)acryloyl group" and "(meth) acrylate" are also the same as (b), and examples thereof include monomers having an oxirane group and an ethylenically unsaturated bond. (b-Ι) (hereinafter sometimes referred to as "(b-Ι)"), a monomer having an oxycyclobutane group and an ethylenically unsaturated bond (b-2) (hereinafter sometimes referred to as "(b- 2)") and a monomer (b-3) having a tetrahydrofuranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b-3)"). (b-1), for example, a monomer (b-1 1 ) having a structure in which a chain olefin is bonded to an ethylenic group via an epoxy group-12-201232174 (hereinafter referred to as "(b-11)" And a monomer (b-12) having a structural unsaturated bond having a cyclic olefin as an epoxy group (hereinafter sometimes referred to as "(b_)° as (b-Ι) to have an oxirane group and A monomer having a (meth)propoxy group is preferred, and a (meth) propylene fluorenyloxy group is more preferred. (b-oxime), specifically, a glycidyl (meth) ester, --methylepoxypropyl (meth) acrylate, β-ethyl ring (meth) acrylate, propylene propylene vinyl ether, hydrazine-vinyl benzyl propyl ether, m-vinyl benzyl ring Oxypropyl propyl ether, ρ-vinylbenzyl ether, α-methyl-hydrazine-ethyl benzyl epoxypropyl ether, α-methyl benzyl epoxypropyl ether, α-methyl -ρ-vinylbenzyloxypropane 2,3-bis(glycidoxymethyl)styrene, 2,4-bis(epoxymethyl)styrene, 2,5-bis(epoxypropyl) Oxymethyl) phenylethyl bis(glycidoxymethyl)styrene, 2,3,4-cis (epoxypropyl) Ethylene, 2,3,5-glycol (glycidoxymethyl)styrene, ginseng (glycidoxymethyl)styrene, 3,4,5-glycol(epoxypropyl)styrene 2,4,6-glycol (glycidoxymethyl)styrene, a compound described in JP-A-7-248625, etc. Examples of (b-12) include ethylene cyclohexene monooxide and oxygen. 4-vinylcyclohexane (for example, celloxide 2000; manufactured by Dicel Co., Ltd.), 3,4-epoxycyclohexyl methacrylate Cyclomer A40®; Dice 1 Chemical Industry Co., Ltd., 3, 4 - when called with ethylene.12)" olefinic group b-12) oxypropyl acrylate epoxy propylene m-ethyl ether, propoxy ί ' 2,6- oxymethyl 2,3 , 6-oxymethyl, special 1,2-ring chemical (for example, epoxy-13-201232174 cyclohexylmethyl methacrylate (such as CyclomerM100; Dicel Chemical Industry Co., Ltd.), formula (I) The compound shown, the compound represented by the formula (II), and the like.

(I) (Π) [In the formulae (I) and (II), R1 and R2 are independently of each other and 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 by a hydroxyl group. . X1 and X2 are independent of each other, and represent a single bond, -R3-, *-R3-0-, and R3-S-'*-R3-NH- ο R3 represents an alkanediyl group having 1 to 6 carbon atoms. * indicates a bond with 0]. Specific examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl 'n-propyl group, an isopropyl group, an η-butyl group, a second butyl group, and a third butyl group. Examples of the hydroxyalkyl group include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, and a 1-hydroxy-1-methyl group. Ethyl, 2-hydroxy-1-methylethyl, 1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl, 4-hydroxybutyl, and the like. The R1 and R2 are preferably a hydrogen atom, a methyl group, a hydroxymethyl 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 methyl 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-1,5 group. · Diyl, hexane-1,6.diyl and the like. -14- 201232174 As χ1 and χ2, a single bond, a methyl group, an ethyl group, a *-CH2-0- (* represents a bond to a ruthenium) group, and a *-CH2CH2-0- group are preferable. More preferably, a single bond, *-CH2CH2-0- group can be mentioned. The compound represented by the formula (I) may, for example, be a compound represented by the formula (1-1) to the formula (b 15). Preferably, the formula (1-1), the formula (Ι·3), the formula (1-5), the formula (1-7), the formula (1-9), the formula (1-11) to the formula (1_) 15). More preferably, it is a formula (1-1), a formula (1-7), a formula (1-9), a formula H^C=CH a b-0-CH2 H2C=CH-C-O-C2H4 H2〇=CH- C—o-c2h4-〇ch3o Η 2〇C—Ο ch3 ο I II Η 2C =CC—O —"CH2

H2c=ch )—C2H4 CH30 h2c ο —C-Ο—C2H4—s

CH3〇 =c—c —〇—C2H4—N H2〇=C

(I-10) ^OH 〇 H2C=C-C—O o .II H2C=CH-C-0 -C2H4-N H CH30 I II Λ · HjC—C—Ο—O *—02^4—5

〇2Η4ΟΗ o I II h2c=c—c—o C—Ο—〇2Η4·^〇 (M3)

(1-15)

The compound represented by the formula (II) may, for example, be a compound represented by the formula (II-1) to the formula 11 -1 5 ). Preferably, the formula (11-1), the formula (!J -15-201232174), the formula (II-5), the formula (II-7), the formula (II-9), and the formula (11-11) are exemplified. Formula (11-15). More preferably, it is a formula (II-1), a formula (II-7), a formula (II-9), and a formula (11-15).

,(ΙΓ-14) ch3〇 I: II C—O—CjH^O'

The compound of the formula (I) and the compound of the formula (II) can each be used singly. Also, these can be mixed at any ratio. When mixing, when the mixing ratio is expressed by molar ratio, it is preferably Formula (I): Formula (II) is 5: 95 to 95: 5, preferably 10: 90 to 90: 10, more preferably 20: 80 to 80: 20 〇 As (b-2), a monomer having an oxycyclobutane group and a (meth) acrylonitrile-16-201232174 oxy group is preferred. Examples of (b-2) include 3-methyl-3-(methyl)propenyloxymethyloxycyclobutane and 3-ethyl-3-(methyl)propenyloxymethyl group. Oxycyclobutane, 3-methyl-3-(methyl)propenyloxyethyloxycyclobutane and 3-ethyl-3-(methyl)propenyloxyethyloxetane as (b-3), a monomer having a tetrahydrofuranyl group and a (meth)acrylenyloxy group is preferred. Specific examples of (b-3) include tetrahydrofurfuryl acrylate (e.g., Biskot V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like. Examples of (c) include methyl (meth) acrylate, ethyl (meth) acrylate, η-butyl (meth) acrylate, and second butyl (meth) acrylate. (meth)acrylic acid alkyl esters such as tributyl (meth) acrylate; cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, tricyclo [5. 2. 1.  〇2,6]decane-8-yl(meth)acrylate (in the technical field, as a customary name is dicyclopentyl (meth) acrylate), dicyclopentyloxyethyl (methyl) (meth)acrylic acid cyclic alkyl esters such as acrylate and isodecyl (meth) acrylate; (meth) acrylate such as phenyl (meth) acrylate or benzyl (meth) acrylate Or arylalkyl esters; dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, diethyl itaconate; 2-hydroxyethyl (meth) acrylate, 2-hydroxyl Hydroxyalkyl esters such as propyl (meth) acrylate; -17- 201232174 联环 [2. 2. 1] Hept-2-ene, 5-methyl linked ring [2. 2. 1] Hept-2-ene, 5-ethylbicyclo[2. 2. 1] Hept-2-ene, 5-hydroxybicyclo[2. 2. 1] Hept-2-ene, 5-hydroxymethyl linked ring [2. 2. 1] Hept-2-ene, 5-(2,-hydroxyethyl)-linked ring [2. 2. 1] Hept-2-ene, 5-methoxy-linked ring [2. 2. 1] Hept-2-ene, 5-ethoxyl linkage [2. 2. 1] Hept-2-ene, 5,6-dihydroxybicyclo[2. 2. 1] Hept-2-ene, 5,6-di(hydroxymethyl)-linked ring [2. 2. 1] Hept-2-ene, 5,6-di(2,-hydroxyethyl) linked ring [2. 2. 1] Hept-2-ene, 5,6-dimethoxy linked ring [2. 2. 1] Hept-2-ene, 5,6-diethoxybicyclo [2. 2. 1] Hept-2-ene, 5-hydroxy-5-methyl linked ring [2. 2. 1] Geng-2_ene, 5-hydroxy-5-ethylbicyclo[2. 2. 1] Hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2. 2. 1] G-8-ene, 5-tributoxycarbonyl linkage _ [2. 2. 1] Hept-2-ene, 5-cyclohexyloxycarbonyl linked ring [2. 2. 1] Hept-2-ene, 5-phenoxycarbonyl ring [2. 2. 1] Hept-2-ene, 5,6-bis(t-butoxycarbonyl)-linked ring [2. 2. 1] Hept-2-ene, 5,6-bis(cyclohexyloxycarbonyl) linked ring [2. 2. 1] Heterocyclic unsaturated compounds such as hept-2-ene; N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-amber Imine-3-maleimide benzoate, N-succinimide-4-maleimide butyrate, N-succinimide-6-maleimide caproate a derivative of dicarbonylimine such as N-succinimide-3-maleimide propionate or N-(9-acridinyl)maleimide; styrene, α-methylbenzene Ethylene, m-methylstyrene, p-methylstyrene, vinyl toluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, ethylene chloride, vinylidene chloride, acrylamide, methyl Acrylamide, vinyl acetate, 1,3-butadiene, isoprene and 2,3-dimethyl-1,3-butadiene-18-201232174, and the like. Among them, styrene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, hydrazine [2. 2. 1] Hept-2-ene or the like is preferred from the viewpoints of copolymerization reactivity and alkali solubility. In the resin (B1-1), the ratio of the structural unit derived from each monomer to the total number of structural units constituting the resin (B1-1) is preferably in the following range. Structural unit from (a); 5 to 6 〇 mol% (more preferably 1 〇 to 5 〇 mol%) Structural unit from (b); 40 to 95 mol% (more preferably 50 to 9 0 When the ratio of the structural unit of the resin (B 1 -1 ) is within the above range, storage stability, developing property, solvent resistance, heat resistance, and mechanical strength tend to be good. The resin (B 1 -1 ) is preferably a resin of (b) (b-1), and more preferably (b-1) is a resin of (b-1 2 ). The resin (B1-1) can be referred to, for example, the method described in the "Experimental Method for Polymer Synthesis" (Otsuka Ryokan, Institute of Chemicals, 1st Edition, 1st Brush, March 1, 1972) and the literature. Manufactured from the cited references. Specifically, a method in which the quantitative amount, polymerization initiator, solvent, and the like of (a) and (b) are charged into a reaction vessel, deoxidized by replacing nitrogen with oxygen, and stirred, heated, and kept warm is exemplified. Further, the polymerization initiator, solvent and the like used therein are not particularly limited, and any of those generally used in the field of -19-201232174 can be used. Examples of the polymerization initiator include an azo compound (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic The oxide (such as benzhydryl peroxide) may be used as a solvent to dissolve the monomer. The solvent to be used as the coloring photosensitive resin composition may be a solvent or the like described later. Further, the obtained copolymer may be used as it is, or a concentrated or diluted solution may be used, or may be taken out as a solid (powder) by reprecipitation or the like. In particular, when a solvent similar to the solvent (E) described below is used as the solvent in the polymerization, the reaction solution can be directly used, and the production step can be simplified. In the resin (B1-2), the ratio of the structural unit derived from each monomer is preferably in the range of the total number of moles of the total structural unit constituting the resin (B1-2). Structural unit from (a); 2 to 40 mol% (more preferably 5 to 35 mol%) from (b) structural unit; 2 to 95 mol% (more preferably 5 to 80 mol%) The structural unit derived from (c); 1 to 65 mol% (more preferably i~60 mol%). If the ratio of the structural unit of the resin (B 1 - 2 ) is within the above range, it has preservation stability and Image, solvent resistance, heat resistance and mechanical strength tend to be good. The resin (B 1 - 2 ) is preferably a resin of (b) (b -1 ), and the resin (b) is (b-12). -20- 201232174 The resin (B1-2) can be produced in the same manner as the resin (B1-1). The polystyrene-equivalent weight average molecular weight (Mw) of the resin (B1) is preferably from 3,000 to 100,0 Torr, more preferably from 5,000 to 50,000. When the weight average molecular weight of the resin (B1) is in the above range, the coating property tends to be good, and the film-reducing phenomenon is unlikely to occur at the time of development, and the non-pixel portion is excellent in the release property at the time of development. tendency. The molecular weight distribution (weight average molecular weight (Mw) / number average molecular weight (?η)) of the resin (B1) is preferably 1. 5~6. 0, more preferably 1. 8~4. 0. When the molecular weight distribution of the resin (Β1) is within the above range, the image forming property tends to be excellent. The acid value of the resin (Β1) is from 20 to 150 mg-KOH/g, preferably from 30 to 135 mg-KOH/g, more preferably from 40 to 125 mg-KOH/g. The oxime measured as a necessary amount (mg) of potassium hydroxide when the acid value is 1 g of the neutralizing resin (B 1 ) can be determined by titration with an aqueous potassium hydroxide solution. The content of the resin (B1) is preferably from 10 to 95% by mass, more preferably from 10 to 85% by mass, based on the total amount of the resin (B1) and the resin (B2), particularly preferably from 10 to 80% by mass. . When the content of the resin (B 1 ) is within the above range, the developing property, the adhesion, the solvent resistance, and the mechanical properties tend to be good. The resin (B) contained in the colored photosensitive resin composition of the present invention further contains a resin (B2). The resin (B2) may be a resin having an ethylenically unsaturated bond in a side chain, and a copolymer obtained by copolymerizing (a) and (c) may be further reacted with (b) to obtain a resin (B2-l) or The copolymer obtained by copolymerizing (b) and (c) is further reacted with (a) to obtain a resin (B2-2) of 21 - 201232174, and the like. Among them, the resin (B2) is preferably a resin (B2-1). (a), (b), and (c) of the constituting resin (B2) are the same as those of the above-mentioned resin (B1), but (c) specifically has a skeleton selected from a tricyclodecane skeleton and At least the group formed by the tricyclic terpene skeleton! A compound (c 1 ) having a skeleton and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(cl)") is preferred. (c) When (cl), it is possible to suppress the pattern-reduction film β by development. The so-called "three-ring brothel skeleton" and "three-ring scorpion skeleton" in the present specification are each of the following structures (each arbitrary carbon atom) To have a binding bond). 〇〇0〇 tricyclodecane skeleton tricyclic terpene skeleton as (cl), specifically dicyclopentyl (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentyloxy Ethyl ethyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate. These may be used alone or in combination of two or more. The resin (B2-1) and the resin (B2-2) can be produced, for example, by a two-stage step. In this case, please refer to the above-mentioned document "Experimental method for polymer synthesis" (the method described in the issue of the 1st edition of the 1st edition of the Otsuka Ryokan, Ltd.). Manufactured by the method described in Japanese Laid-Open Patent Publication No. Hei No. 89-533533. The resin (B 2 -1 ) is obtained as a first step, and a copolymer of (a) and (c) is obtained in the same manner as in the production method of the above resin (B 1 - 1 ). In this case, as in the above, the obtained copolymer may be directly used as a solution after the reaction, -22 to 201232174, or may be taken out as a solid (powder) by reprecipitation or the like using a concentrated or diluted solution. The ratio of (a) and the structural unit derived from (c) is preferably in the range of the total number of moles constituting the entire structural unit of the above-mentioned copolymer. Structural unit from (a); 5 to 5 0 mol% (more preferably 1 〇 ~ 4 5 mol %) Structural unit from (c); 50 to 95 mol% (more preferably 55 to 9 0 Mohr %) Next, as a second stage, a part of the carboxylic acid and the carboxylic anhydride of (a) from the obtained copolymer is reacted with the cyclic ether of (b). Since the cyclic ether has high reactivity and does not easily remain unreacted (b), it is preferable that (b) is (b-Ι), and (b-1 1 ) is more preferable. Specifically, in order to continue the above, the environment inside the beaker is replaced by nitrogen, and the reaction catalyst for the (15) molar number of (a) is 5 to 80 mol%, and the carboxyl group and the cyclic ether are reacted (for example, Methylaminomethyl phenol) is a total of 0 for (a), (b) and (c). 001 to 5 mass%, and the total amount of the polymerization inhibitor (for example, hydroquinone) for (a), (b), and (c) is 0. 001 to 5 mass% were placed in a beaker, and the reaction was carried out at 60 to 130 ° C for 1 to 1 hour, to obtain a resin (B 2 -1 ). Further, in the same manner as in the polymerization conditions, the charging method or the reaction temperature can be appropriately adjusted in consideration of the heat generation amount due to the production equipment or the polymerization. Further, the number of moles in the case (b) at this time is preferably from 10 to 7 mol%, more preferably from 5 to 7 mol%, to the number of moles of (a). When the number of motes of (b) is in this range, the balance between stability, solvent resistance and heat resistance is maintained. -23- 201232174 tends to be good. As a specific example of the resin (B2-1), a copolymer of (meth)acrylic acid/dicyclopentyl (meth)acrylate is reacted with a resin of a glycidyl (meth)acrylate, and (meth)acrylic acid / Benzyl (meth) acrylate copolymer in the reaction of epoxy propyl (meth) acrylate resin, (meth) acrylate / cyclohexyl (meth) acrylate copolymer in the reaction of propylene (meth)acrylate resin, (meth)acrylic acid/styrene copolymer in the reaction of epoxy propyl (meth) acrylate resin, (meth)acrylic acid / (meth)acrylic acid methyl group a resin for reacting a glycidyl (meth) acrylate in a copolymer of a copolymer of a reactive propylene group (meth) acrylate, a copolymer of (meth)acrylic acid/N-cyclohexylmaleimide; a resin reactive with epoxypropyl (meth) acrylate in a copolymer of crotonic acid/dicyclopentyl (meth) acrylate; a reactive epoxy in a copolymer of crotonic acid/benzyl (meth) acrylate Propyl (meth) acrylate resin, crotonic acid / cyclohexyl (Resin for reacting epoxy propyl (meth) acrylate in a copolymer of (meth) acrylate, a resin reactive with epoxy propyl (meth) acrylate in a copolymer of crotonic acid / styrene, crotonic acid / Reaction of epoxypropyl (meth) acrylate in a copolymer of reactive propyl propyl (meth) acrylate and a copolymer of crotonic acid / N-cyclohexyl maleimide in a copolymer of crotonic acid methyl Resin ♦ copolymer of maleic acid/dicyclopentyl (meth) acrylate copolymer of epoxy propyl (meth) acrylate, copolymer of maleic acid / benzyl (meth) acrylate Reaction of epoxy propyl (meth) acrylate-24- 201232174 resin, copolymer of maleic acid/cyclohexyl (meth) acrylate, reaction of epoxy propyl (meth) acrylate resin, horse a resin for reacting a glycidyl (meth) acrylate in a copolymer of a reactive propylene group (meth) acrylate and a copolymer of maleic acid / methyl maleate in a copolymer of acid/styrene; Reaction of epoxy propylene in copolymer of maleic acid/N-cyclohexylmaleimide (meth)acrylate resin; (meth)acrylic acid / maleic anhydride / dicyclopentyl (meth) acrylate copolymer in the reaction of epoxy propyl (meth) acrylate resin, (methyl) Resin reactive propyl (meth) acrylate resin, (meth) acrylate / maleic anhydride / cyclohexyl (meth) acrylate in a copolymer of acrylic acid / maleic anhydride / benzyl (meth) acrylate a resin for reacting a glycidyl (meth) acrylate in a copolymer of an ester, and a resin reactive with a propylene propyl (meth) acrylate in a copolymer of (meth)acrylic acid/maleic anhydride/styrene; (meth)acrylic acid/maleic anhydride/N-cyclohexylmalay reacted with a copolymer of methyl methacrylate/maleic anhydride/methyl (meth) acrylate in a copolymer of epoxy propyl (meth) acrylate a resin reactive with epoxypropyl (meth) acrylate in a copolymer of decylamine; a 3,4-epoxy ring in a copolymer of (meth)acrylic acid/dicyclopentyl (meth) acrylate Hexylmethyl methacrylate resin, (meth)acrylic acid / benzyl group In the copolymer of (meth) acrylate, the reaction of 3,4-epoxycyclohexylmethyl methacrylate resin and (meth)acrylic acid/cyclohexyl (meth) acrylate copolymer 3, Resin of 4-epoxycyclohexylmethyl methacrylate resin and (meth)acrylic acid/styrene copolymer 3,4-epoxycyclohexylmethyl methacrylate-25-201232174 a resin of 3,4-epoxycyclohexylmethyl methacrylate in a copolymer of (meth)acrylic acid / methyl methacrylate, (meth)acrylic acid / N-cyclohexylmala Resin for the reaction of 3,4-epoxycyclohexylmethyl methacrylate in a copolymer of decylamine; 3,4-epoxy group in a copolymer of crotonic acid/dicyclopentyl (meth) acrylate a resin for reacting 3,4-epoxycyclohexylmethyl methacrylate with a resin of cyclohexylmethyl methacrylate or a copolymer of crotonic acid/benzyl (meth) acrylate, crotonic acid/ring a tree for reacting 3,4-epoxycyclohexylmethyl methacrylate in a copolymer of hexyl (meth) acrylate 3,4-epoxycyclohexyl group in a copolymer of crotonic acid/styrene in a copolymer of 3,4-epoxycyclohexylmethyl methacrylate and a copolymer of crotonic acid/methyl crotonate a resin for reacting 3,4-epoxycyclohexylmethyl methacrylate in a copolymer of methyl methacrylate or a copolymer of crotonic acid/N-cyclohexylmaleimide; maleic acid/bicyclic ring Reaction of a copolymer of pentyl (meth) acrylate in a copolymer of 3,4 _epoxycyclohexylmethyl methacrylate and a copolymer of maleic acid/benzyl (meth) acrylate 3 , a copolymer of 4-epoxycyclohexylmethyl methacrylate, a copolymer of maleic acid/cyclohexyl (meth) acrylate, reacted with 3,4-epoxycyclohexylmethyl methacrylate 3,4-ring reaction in a copolymer of resin, maleic acid/styrene in a resin of 3,4-epoxycyclohexylmethyl methacrylate and a copolymer of maleic acid/maleic acid methyl Reaction of 3,4-epoxycyclohexylmethyl group in a copolymer of oxycyclohexylmethyl methacrylate and a copolymer of maleic acid/N-cyclohexylmaleimide Acrylate resin; -26- 201232174 Reaction of 3,4-epoxycyclohexylmethyl methacrylate in a copolymer of (meth)acrylic acid/maleic anhydride/dicyclopentyl (meth) acrylate a resin for reacting 3,4-epoxycyclohexylmethyl methacrylate in a copolymer of (meth)acrylic acid/maleic anhydride/benzyl (methyl)propionate, (methyl) Resin for the reaction of 3,4-epoxycyclohexylmethyl methacrylate in a copolymer of acrylic acid/maleic anhydride/cyclohexyl (meth) acrylate, (meth)acrylic acid/maleic anhydride/styrene a copolymer of 3,4-epoxycyclohexylmethyl methacrylate, a copolymer of (meth)acrylic acid/maleic anhydride/methyl (meth)acrylic acid in a copolymer, 3,4-ring 3,4-Epoxycyclohexylmethylmethyl group in a copolymer of oxycyclohexylmethyl methacrylate and a copolymer of (meth)acrylic acid/maleic anhydride/N-cyclohexylmaleimide Acrylate resin, etc. As the resin (B2-1), in the copolymer obtained by (c) other than (a), (cl) and (cl), the resin obtained in the reaction (b) is preferred. When the resin (B2-1) is in the above-described configuration, the resulting pattern and the substrate have a tendency to be excellent in adhesion and solvent resistance. (a) The copolymer of (c) is composed of (c) other than (a), (cl) and (cl), and the structure derived from (c) other than (c 1 ) and (c 1 ) The ratio of units is preferably 1 0 : 9 0 to 6 0 : 4 0 , preferably 1 0 : 9 0 to 40: 60, and 10: 90 to 30: 70 is better. The resin obtained by the reaction (b) in the copolymer obtained by copolymerizing (c) other than (a), (cl) and (cl), specifically (meth)acrylic acid / dicyclopentyl (A) Resin for the reaction of epoxypropyl (meth) acrylate in a copolymer of acrylate/benzyl (meth) acrylate -27- 201232174 , (meth)acrylic acid / dicyclopentyl (methyl) Reaction of epoxy propyl (molecular resin, (meth)acrylic acid / dicyclopentyl (reactive epoxypropyl (meth) propyl in copolymer of methyl styrene) Reaction of epoxy (meth) acrylate, (meth) acrylate / dicyclopentyl (methyl) acrylate in a copolymer of (meth)acrylic acid / dicyclopentyl (meth) acrylate methacrylate , a copolymer of hexylmalamine decylamine in the reaction of epoxy propyl (methyl ester resin; crotonic acid / dicyclopentyl (meth) acrylate / benzo acrylate copolymer in the reaction of epoxy propyl ( a copolymer of methyl) propyl ester, crotonic acid/dicyclopentyl (meth) acrylate/cyclohexyl acrylate Epoxypropyl (meth) propyl ester, crotonic acid / dicyclopentyl (meth) acrylate / phenyl ethyl epoxide reactive propyl propyl (meth) acrylate resin, [ pentyl (methyl) Acrylate/crotonic acid methyl copolymer propyl (meth) acrylate resin, crotonic acid / bicyclo) acrylate / N-cyclohexyl maleimide copolymer medium (meth) acrylate Resin; maleic acid / dicyclopentyl (meth) acrylate / benzo acrylate copolymer in the reaction of epoxy propyl (methyl) propyl ester 'maleic acid / dicyclopentyl (methyl) Reaction of epoxy acrylate (meth) propyl ester, maleic acid / dicyclopentyl (meth) acrylate / phenethyl ester / cyclohexyl (meth) acrylate in the copolymer of acrylate / cyclohexyl acrylate Acrylate / acrylate ester resin vinegar / (meth) acrylate diester / oxime - ring) acrylate (meth) enoate tree (meth) enoate copolymerization of alkene Compound 3 in the stucic acid/bicyclic reaction of epoxypentyl (methyl-reactive epoxypropyl (meth) enoate tree (meth) enoate tree Epene copolymer -28- 201232174 Reactive epoxy propylene (meth) acrylate resin, maleic acid / dicyclopentyl (meth) acrylate / maleic acid methyl copolymer copolymer epoxy Reaction of epoxypropyl (meth) acrylate in a copolymer of propyl (meth) acrylate, copolymer of maleic acid / dicyclopentyl (meth) acrylate / N-cyclohexylmaleimide Resin; (meth)acrylic acid / maleic anhydride / dicyclopentyl (meth) acrylate / benzyl (meth) acrylate copolymer in the reaction of epoxy propyl (meth) acrylate resin a resin for reacting epoxypropyl (meth) acrylate in a copolymer of (meth)acrylic acid/maleic anhydride/dicyclopentyl (meth) acrylate/cyclohexyl (meth) acrylate, (a) (meth)acrylic acid/maleic anhydride/dimer in the copolymer of acrylic acid/maleic anhydride/dicyclopentyl (meth)acrylate/styrene in the copolymer of epoxypropyl (meth)acrylate Reaction of epoxy propyl group in a copolymer of cyclopentyl (meth) acrylate / methyl (meth) acrylate Reaction of a methyl acrylate resin, a copolymer of (meth)acrylic acid/maleic anhydride/dicyclopentyl (meth) acrylate/N-cyclohexylmaleimide, a glycidyl group (methyl group) Acrylate resin; 3,4-epoxycyclohexylmethylmethyl group in a copolymer of (meth)acrylic acid/dicyclopentyl (meth) acrylate/benzyl (meth) acrylate Reaction of 3,4-epoxycyclohexylmethyl methacrylate in an acrylate resin, a copolymer of (meth)acrylic acid/dicyclopentyl (meth) acrylate/cyclohexyl (meth) acrylate Resin, (meth)acrylic acid / dicyclopentyl (meth) acrylate / styrene copolymer in the reaction of 3,4-epoxycyclohexylmethyl methacrylate resin, (meth) propyl -29- 201232174 Resin for the reaction of 夂4-epoxycyclohexylmethyl methacrylate in a copolymer of enoic acid/dicyclopentyl (meth) acrylate / methyl (meth) acrylate, (methyl Reaction of 3,4-ring in a copolymer of acrylic acid/dicyclopentyl, (meth) acrylate/N-cyclohexylmaleimide Resin of cyclohexylmethyl methacrylate; reaction of crotonic acid/dicyclopentyl (meth) acrylate/benzyl (meth) acrylate in 3,4-epoxycyclohexyl Reaction of 3,4-epoxycyclohexylmethyl methacrylate in a methacrylate resin, a copolymer of crotonic acid/dicyclopentyl (meth) acrylate/cyclohexyl (meth) acrylate Resin, a copolymer of crotonic acid/dicyclopentyl (meth) acrylate/styrene, a resin for reacting 3,4-epoxycyclohexylmethyl methacrylate, crotonic acid/dicyclopentyl ( Resin for the reaction of 3,4-epoxycyclohexylmethyl methacrylate in a copolymer of methyl acrylate/crotonate methyl, crotonic acid/dicyclopentyl (meth) acrylate/N-ring Resin for the reaction of 3,4-epoxycyclohexylmethyl methacrylate in a copolymer of hexylmalamine amide; maleic acid/dicyclopentyl (meth) acrylate/benzyl (methyl) Resin for the reaction of 3,4·epoxycyclohexylmethyl methacrylate in an acrylate copolymer, maleic acid/dicyclopentyl (A) a resin for reacting 3,4-epoxycyclohexylmethylmethyl citrate in a copolymer of acrylate/cyclohexyl (meth) acrylate, maleic acid/dicyclopentyl (methyl) propyl Resin for the reaction of 3,4-epoxycyclohexylmethyl methacrylate in copolymer of acrylate/styrene, maleic acid/dicyclopentyl (meth) acrylate/methyl maleate Resin 3,4-epoxycyclohexylmethyl methacrylate-30- 201232174 ester resin, maleic acid / dicyclopentyl (meth) acrylate / N-cyclohexylmalay yttrium Resin for the reaction of 3,4-epoxycyclohexylmethyl methacrylate in a copolymer of amine; (meth)acrylic acid/maleic anhydride/dicyclopentyl (meth) acrylate/benzyl (a) Resin for the reaction of 3,4-epoxycyclohexylmethyl methacrylate in a copolymer of acrylate, (meth)acrylic acid/maleic anhydride/dicyclopentyl (meth) acrylate/cyclohexyl Resin (meth)acrylic acid/maleic anhydride/dicyclopentane which reacts 3,4-epoxycyclohexylmethyl methacrylate in a copolymer of (meth) acrylate Resin for the reaction of 3,4-epoxycyclohexylmethyl methacrylate in a copolymer of methacrylate/styrene, (meth)acrylic acid/maleic anhydride/dicyclopentyl (methyl) a resin for reacting 3,4-epoxycyclohexylmethyl methacrylate in a copolymer of acrylate / methyl (meth) acrylate, (meth)acrylic acid / maleic anhydride / dicyclopentyl (A) A resin of 3,4-epoxycyclohexylmethyl methacrylate or the like is reacted in a copolymer of acrylate/N-cyclohexylmaleimide. The resin (B2-2) is obtained as a first stage, and a copolymer of (b) and (c) is obtained in the same manner as in the production method of the above resin (B1-1). At this time, as in the above, the obtained copolymer may be used as it is as a solid (powder) by directly using the solution after the reaction, or by using a concentrated or diluted solution by reprecipitation or the like. The ratio of (b) and the structural unit derived from (c) is preferably in the following range for the total number of moles constituting the entire structural unit of the above copolymer. Structural unit from (b); 5 to 95 mol% (more preferably 1〇~90 -31 - 201232174 mol%) Structural unit from (c); 5~9 5 mol% (better 1 In the same manner as in the production method of the resin (Β2-1), the cyclic ether of (b) from the copolymer of (b) and (c) has a reaction (a). The carboxylic acid or carboxylic anhydride obtained. The hydroxyl group produced by the reaction of a cyclic ether with a carboxylic acid or a carboxylic acid anhydride can be further reacted with a carboxylic acid anhydride. The amount of (a) used for the reaction of the copolymer described above is preferably from 5 to 80 mol% based on the number of moles of (b). The cyclic ether has high reactivity, and the unreacted (b) is hard to remain. Therefore, (b) is preferably (b-1), more preferably (b-11). Specific examples of the resin (B2-2) include a resin (meth)acrylic acid in which a copolymer of dicyclopentyl (meth)acrylate/epoxypropyl (meth)acrylate is reacted, and benzoic acid. Reactive (meth)acrylic resin, cyclohexyl (meth) acrylate / epoxy propyl (meth) acrylate in a copolymer of a base (meth) acrylate / epoxy propyl (meth) acrylate a copolymer of (meth)acrylic acid, a copolymer of styrene/epoxypropyl (meth)acrylate in a copolymer of (meth)acrylic acid, (meth)acrylic acid methyl/epoxypropyl Reaction of (meth)acrylic acid in a copolymer of (meth)acrylic acid, copolymer of N-cyclohexylmaleimide/epoxypropyl (meth)acrylate in a copolymer of a (meth) acrylate Resin, dicyclopentyl (meth) acrylate / benzyl (meth) acrylate / epoxy propyl (meth) acrylate copolymer (meth) acrylic resin, dicyclopentane (meth)acrylic acid-32- 201232174 ester / cyclohexyl (methyl) propyl Acid ester/epoxypropyl group (resin for reacting (meth)acrylic acid in copolymer of methyl, b) resin for reacting (meth)acrylic acid in acrylate/styrene/epoxypropyl (meth) propylene, ( Dicyclopentyl. Acid ester / methyl (meth)acrylate / epoxy propyl (reactive (meth)acrylic resin in methyl copolymer, bicycloacrylate / N_cyclohexylmaleimide / epoxy propyl ( a resin for reacting (meth)acrylic acid in an ester copolymer; a resin for reacting crotonic acid in a copolymer of dicyclopentyl (meth) acrylate/epoxypropyl acrylate, benzyl ester/epoxy propyl Reaction of croton in a copolymer of a copolymer of a (meth) acrylate, a copolymer of a cyclohexyl (meth) acrylate/epoxy acrylate in a copolymer of a crotonic acid, and a copolymer of a benzene Z (meth) acrylate Resin of copolymer of acid methyl/epoxypropyl (meth) acrylate, N-cyclohexylmaleimide/epoxypropyl (resin for the reaction of crotonic acid in the copolymer of ester, dicyclopentane Acid ester / benzyl (meth) acrylate / epoxy propyl (resin for the reaction of crotonic acid in the copolymer of ester, dicyclopentyrate / cyclohexyl (meth) acrylate / epoxy propyl (Resin for the reaction of crotonic acid in a copolymer of ester, dicyclopentyl acrylate/styrene/epoxypropyl (methyl) Resin of acrylated crotonic acid resin, copolymer of dicyclopentyl (meth) acrylate epoxypropyl (meth) acrylate) acrylate cyclopentyl (copolymer of methyl ester (A Reaction of crotonyl (meth) meth) methacrylate (meth) propylene (meth) propylene in the reaction of crotonic acid (meth) propylene / epoxy propyl resin, crotonic acid in the reaction of crotonic acid Methyl)acrylic (meth)acryloyl-(meth)acrylic (meth)acrylomethyl)acrylic acid (meth) propylene copolymer reaction / crotonic acid methyl / crotonic acid resin -33- 201232174, dicyclopentan a resin for reacting crotonic acid in a copolymer of a base (meth) acrylate/N_cyclohexylmaleimide/epoxypropyl (meth) acrylate; a dicyclopentyl (meth) acrylate/ring a resin for reacting maleic acid in a copolymer of maleic acid and a copolymer of benzyl (meth)acrylate/epoxypropyl (meth)acrylate in a copolymer of oxypropyl (meth)acrylate Cyclohexyl (meth) acrylate / epoxy propyl (A a copolymer of maleic acid, a copolymer of styrene/epoxypropyl (meth)acrylate in a copolymer of acrylate, a maleic acid-reactive resin, a maleic acid methyl/epoxypropyl group (a) a resin of maleic acid in a copolymer of acrylates, a copolymer of N-cyclohexylmaleamide/epoxypropyl (meth) acrylate, a resin of maleic acid, 'dicyclopentyl Resin of maleic acid, dicyclopentyl (meth) acrylate / ring in copolymer of (meth) acrylate / benzyl (meth) acrylate / epoxy propyl (meth) acrylate Resin for the reaction of maleic acid in a copolymer of hexyl (meth) acrylate/epoxypropyl (meth) acrylate, dicyclopentyl (meth) acrylate / styrene / epoxy propyl (methyl Reaction of maleic acid in a copolymer of maleic acid, copolymer of dicyclopentyl (meth) acrylate/maleic acid methyl/epoxypropyl (meth) acrylate in an acrylate copolymer Resin dicyclopentyl (meth) acrylate / N_cyclohexylmaleimide / epoxy propyl (methyl) propyl a resin for reacting maleic acid in a copolymer of an acid ester; a reaction of (meth)acrylic acid and maleic anhydride in a copolymer of a cyclopentyl (meth) acrylate/epoxypropyl (meth) acrylate Resin, benzyl (meth) acrylate / epoxy propyl (meth) acrylate copolymer (meth) acrylic acid and maleic anhydride resin, cyclohexyl-34- 201232174 (meth) acrylate Reaction of a copolymer of (meth)acrylic acid and maleic anhydride with a copolymer of styrene/epoxypropyl (meth) acrylate in a copolymer of ester/glycidyl (meth) acrylate (A Resin (meth)acrylic acid and maleic anhydride resin (N-cyclohexyl) in a copolymer of acrylic acid and maleic anhydride, or a copolymer of methyl (meth)acrylate/methyl acrylate (meth)acrylate Reaction of (meth)acrylic acid and maleic anhydride resin, dicyclopentyl (meth) acrylate / benzyl (methyl) in a copolymer of maleic amine / glycidyl (meth) acrylate Acrylate/epoxypropyl (meth) acrylate copolymer Reaction of (meth)acrylic acid and maleic anhydride resin, copolymer of dicyclopentyl (meth) acrylate / cyclohexyl (meth) acrylate / epoxy propyl (meth) acrylate (A) Resin (meth)acrylic acid and maleic anhydride resin in a copolymer of acrylic acid and maleic anhydride, a copolymer of dicyclopentyl (meth) acrylate/styrene/epoxypropyl (meth) acrylate Resin (meth)acrylic acid and maleic anhydride resin, dicyclopentane in a copolymer of dicyclopentyl (meth) acrylate / methyl (meth) acrylate / epoxy propyl (meth) acrylate Resin (meth)acrylic acid and maleic anhydride resin in copolymer of (meth) acrylate/N-cyclohexylmaleimide/epoxypropyl (meth) acrylate; dicyclopentyl ( Reaction of (meth)acrylic resin, benzyl (meth) acrylate / 3, 4-epoxy in a copolymer of methyl acrylate / 3, 4-epoxycyclohexyl methyl methacrylate Resin (meth)acrylic resin in a copolymer of cyclohexylmethyl methacrylate , a copolymer of cyclohexyl (meth) acrylate / 3,4-epoxycyclohexylmethyl methacrylate -35 - 201232174 Reactive (meth)acrylic resin, styrene / 3,4 - ring a copolymer of (meth)acrylic acid, a copolymer of methyl (meth)acrylate/3,4-epoxycyclohexylmethyl methacrylate in a copolymer of oxycyclohexylmethyl methacrylate Reaction of (meth)acrylic resin, copolymer of N-cyclohexylmaleimide/3,4-epoxycyclohexylmethyl methacrylate, reaction of (meth)acrylic acid resin, dicyclopentane Resin (meth)acrylic resin, dicyclopentyl group in a copolymer of a base (meth) acrylate / benzyl (meth) acrylate / 3, 4-epoxycyclohexyl methyl methacrylate Resin (meth)acrylic resin, dicyclopentyl (a) in a copolymer of (meth) acrylate/cyclohexyl (meth) acrylate / 3,4-epoxycyclohexylmethyl methacrylate Reaction in a copolymer of acrylate/styrene/3,4-epoxycyclohexylmethyl methacrylate Reaction of (meth)acrylic acid in a copolymer of acrylic acid, dicyclopentyl (meth) acrylate / methyl (meth) acrylate / 3, 4-epoxycyclohexyl methyl methacrylate Resin (meth)acrylic resin in a copolymer of dicyclopentyl (meth) acrylate/N-cyclohexylmaleimide/3,4-epoxycyclohexylmethyl methacrylate : a resin for reacting crotonic acid in a copolymer of dicyclopentyl (meth) acrylate/3,4-epoxycyclohexylmethyl methacrylate, benzyl (meth) acrylate / 3, 4 - a copolymer of crotonic acid, a copolymer of cyclohexyl (meth) acrylate / 3,4-epoxycyclohexylmethyl methacrylate in a copolymer of epoxy-cyclohexylmethyl methacrylate a resin for reacting crotonic acid, a copolymer of styrene/3,4-epoxycyclohexylmethyl methacrylate, a crotonic acid-reactive resin, a crotonic acid methyl/3,4-epoxycyclohexylmethyl group Resin for the reaction of crotonic acid in a copolymer of A-36-201232174 acrylate, N-cyclohexylmaleimide/3,4-epoxy ring Resin for the reaction of crotonic acid in a copolymer of methyl methacrylate, dicyclopentyl (meth) acrylate / benzyl (meth) acrylate / 3, 4-epoxycyclohexylmethyl Copolymerization of crotonic acid-reactive resin, dicyclopentyl (meth) acrylate / cyclohexyl (meth) acrylate / 3,4-epoxycyclohexylmethyl methacrylate in a copolymer of acrylate a resin for reacting crotonic acid, a copolymer of dicyclopentyl (meth) acrylate/styrene/3,4-epoxycyclohexylmethyl methacrylate, a resin for reacting crotonic acid, and dicyclopentane Resin for the reaction of crotonic acid, dicyclopentyl (meth) acrylate/N in a copolymer of a base (meth) acrylate / crotonic acid methyl / 3,4-epoxycyclohexylmethyl methacrylate a resin for reacting crotonic acid in a copolymer of cyclohexylmaleimide/3,4-epoxycyclohexylmethyl methacrylate; dicyclopentyl (meth) acrylate/3,4-ring Maleic acid-reactive resin, benzyl (meth) acrylate / 3, 4- in a copolymer of oxycyclohexyl methyl methacrylate a copolymer of maleic acid, a copolymer of cyclohexyl (meth) acrylate / 3,4-epoxycyclohexylmethyl methacrylate in a copolymer of epoxycyclohexylmethyl methacrylate Reaction of maleic acid resin, copolymer of styrene/3,4-epoxycyclohexylmethyl methacrylate, maleic acid resin, maleic acid methyl/3,4-epoxy ring Reaction of maleic acid resin, copolymer of N-cyclohexylmaleimide/3,4-epoxycyclohexylmethyl methacrylate in copolymer of hexylmethyl methacrylate Reaction of acid resin 'dicyclopentyl (meth) acrylate / benzyl (meth) acrylate / 3, 4-epoxycyclohexyl methyl methacrylate - 37 - 201232174 Maleic acid in a copolymer of maleic acid, dicyclopentyl (meth) acrylate / cyclohexyl (meth) acrylate / 3,4-epoxycyclohexylmethyl methacrylate a resin of maleic acid in a copolymer of a resin, dicyclopentyl (meth) acrylate / styrene / 3,4-epoxycyclohexylmethyl methacrylate a resin of maleic acid, dicyclopentyl (A) in a copolymer of dicyclopentyl (meth) acrylate / maleic acid methyl / 3,4-epoxycyclohexylmethyl methacrylate Resin for the reaction of maleic acid in a copolymer of acrylate/N-cyclohexylmaleimide/3,4-epoxycyclohexylmethyl methacrylate; dicyclopentyl (meth)acrylic acid Reaction of (meth)acrylic acid and maleic anhydride resin, benzyl (meth) acrylate / 3, 4- epoxy in copolymer of ester / 3,4-epoxycyclohexylmethyl methacrylate Resin (meth)acrylic acid and maleic anhydride resin, cyclohexyl (meth) acrylate / 3,4-epoxycyclohexylmethyl methacrylate in a copolymer of cyclohexylmethyl methacrylate (meth)acrylic acid and maleic anhydride in a copolymer of (meth)acrylic acid and maleic anhydride resin, styrene/3,4-epoxycyclohexylmethyl methacrylate Reaction of a resin, a copolymer of methyl (meth)acrylate/3,4-epoxycyclohexylmethyl methacrylate (methyl) Resin (meth)acrylic acid and maleic anhydride resin in copolymer of enoic acid and maleic anhydride, copolymer of N-cyclohexylmaleimide/3,4-epoxycyclohexylmethyl methacrylate (Meth)acrylic acid and Malay in a copolymer of dicyclopentyl (meth) acrylate / benzyl (meth) acrylate / 3, 4-epoxycyclohexyl methyl methacrylate Reaction of an anhydride resin, a copolymer of dicyclopentyl (meth) acrylate / cyclohexyl (methyl) propyl - 38 - 201232174 enoate / 3,4-epoxycyclohexylmethyl methacrylate Reaction of (meth)acrylic acid and maleic anhydride resin, copolymer of dicyclopentyl (meth) acrylate / styrene / 3,4-epoxycyclohexylmethyl methacrylate (methyl) Reaction of acrylic acid and maleic anhydride resin, copolymer of dicyclopentyl (meth) acrylate / methyl (meth) acrylate / 3, 4-epoxycyclohexyl methyl methacrylate (methyl Acrylic acid and maleic anhydride resin, dicyclopentyl (meth) acrylate / N · cyclohexyl maleimide / 3, 4 - epoxy Copolymers of methyl hexyl acrylate reaction (meth) acrylic acid and maleic anhydride resins. The polystyrene-equivalent weight average molecular weight (Mw) of the resin (B2) is preferably from 3,000 to 100,000, more preferably from 5,000 to 50,000. When the weight average molecular weight of the resin (B2) is in the above range, the coating property tends to be good, and it is difficult to cause a film-reducing phenomenon when developing, and the non-pixel portion has a good tendency to be removed during development. The molecular weight distribution (weight average molecular weight (Mw) / number average molecular weight (?n)) of the resin (B2) is preferably 1. 5~6. 0, more preferably 1. 8~4. 0. When the molecular weight distribution of the resin (Β2) is within the above range, it tends to be excellent in developability. The acid value of the resin (Β2) is from 20 to 150 mg-KOH/g, preferably from 50 to 135 mg-KOH/g, more preferably from 65 to 135 mg-KOH/g. The acid value is determined by measuring the amount (mg) of potassium hydroxide in the case of 1 g of the resin (B2), and can be determined by titration with an aqueous potassium hydroxide solution. The content of the resin (B 2 ) is preferably from 5 to 90% by mass, more preferably from 15 to 90% by mass based on the total amount of the resin (B 1 ) and the resin (B2 ).

C -39- 201232174 % Exceptional is 20 to 90% by mass. When the content of the resin (B 1 ) is within the above range, the developing property, the adhesion, the solvent resistance, and the mechanical properties tend to be good. The colored photosensitive resin composition of the present invention may contain a resin (BX) different from the resin (B1) and the resin (B2) as the resin (B). Examples of the resin (BX) include copolymers of (a) and (c). The content of the resin (BX) is preferably 5% to 5% by mass based on the total mass of the resin (B), and preferably 0 to 30% by mass. The total mass of the resin (B) contained in the colored photosensitive resin composition of the present invention is preferably 20 to 70% by mass, and preferably 25 to 50% by mass, based on the solid content of the colored photosensitive resin composition. good. In addition, the total amount of the resin (B) is preferably 20 to 80% by mass, and preferably 40 to 60% by mass, based on the total amount of the resin (B) and the polymerizable compound (C). The colored photosensitive resin composition of the present invention contains a polymerizable compound (C). The polymerizable compound (C) is a compound obtained by polymerizing an active radical derived from a polymerization initiator (D), an acid or the like, and examples thereof include a compound having an ethylenically unsaturated bond, and preferably a compound. A (meth) acrylate compound is mentioned. The polymerizable compound (C) having one ethylenically unsaturated bond may, for example, be the same compound as mentioned in the above (a), (b) and (c), wherein (meth)acrylate is preferred. . The polymerizable compound (c) -40 - 201232174 having two ethylenically unsaturated bonds can be exemplified as 1,3-butanediol di(meth)acrylate, hydrazine, 3-butanediol (methyl) Acrylate, 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, neopentyl glycol di(a) Acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, polyethylene glycol diacrylate, bisphenol A bis(acryloxyethyl) Ether, ethoxylated bisphenol A di(meth) acrylate, propoxylated neopentyl glycol di(meth) acrylate, ethoxylated neopentyl glycol di(meth) acrylate, 3 -methylpentanediol di(meth)acrylate or the like. Examples of the polymerizable compound (C) having three or more ethylenically unsaturated bonds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, and bis(2·hydroxyl). Trimeric isocyanate tri(meth)acrylate, ethoxylated trimethylolpropane tri(meth)acrylate, propoxylated trimethylolpropane tri(meth)acrylate, pentaerythritol tetra ( Methyl) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tripentaerythritol tetra (meth) acrylate, tripentaerythritol penta (meth) acrylate, tripentaerythritol hexa a reaction of a methyl acrylate, a tripentaerythritol hepta (meth) acrylate, a tripentaerythritol octa (meth) acrylate, a pentaerythritol tri C meth acrylate with an acid anhydride, dipentaerythritol penta (meth) acrylate and Anhydride reactant, tripentaerythritol hepta (meth) acrylate and anhydride caprolactone denatured trimethylolpropane tri(methyl) acrylate vinegar, caprolactone denatured pentaerythritol (Meth) acrylate, caprolactone denatured ginseng (2-hydroxyethyl) trimer isocyanate tri(meth) acrylate, hexa-41 - 201232174 vinegar denatured pentaerythritol tetra(meth) acrylate 'caprolactone Denatured dipentaerythritol penta (meth) acrylate, caprolactone denatured dipentaerythritol hexa(methyl) acrylate vinegar, caprolactone denatured tripentaerythritol tetrakis(methyl) propionate, caprolactone denatured pentaerythritol (Meth) acrylate, caprolactone denatured tripentaerythritol hexa(meth) acrylate, caprolactone denatured tripentaerythritol hepta (methyl) propionate, caprolactone denatured tripentaerythritol octa (meth) acrylate a reaction of caprolactone-denatured pentaerythritol tri(meth)acrylate with an acid anhydride, a reaction of caprolactone-denatured dipentaerythritol penta(meth)acrylate with an acid anhydride, and caprolactone-denatured tripentaerythritol hepta(meth)acrylic acid a reactant of an ester and an acid anhydride, and the like. Among them, a trifunctional or higher monomer is preferred, and dipentaerythritol hexa(meth)acrylate is preferred. The content of the polymerizable compound (C) is preferably 5 to 50% by mass, and preferably 10 to 45% by mass, based on the amount of the solid content of the colored photosensitive resin composition. Further, the total amount of the resin (b) and the polymerizable compound (c) is preferably 20 to 80% by mass, more preferably 40 to 60% by mass. When the content of the polymerizable compound (C) is in the above range, the sensitivity, the strength, the smoothness, and the reliability of the pattern tend to be improved.

The colored photosensitive resin composition of the present invention contains a polymerization initiator (D) ° as a polymerization initiator (D), which generates active radicals and acids by light action, and is a starting polymerizable compound (C). The compound to be polymerized is not particularly limited, and a known polymerization initiator can be used. As the polymerization initiator (D), a diimidazole compound [alkyl phenone compound, triazine compound, mercaptophosphine oxide compound, hydrazine compound -42-201232174 is preferably used. Further, a photocationic polymerization initiator (for example, a composition derived from a gun cation and an anion of Lewis acid) described in JP-A-2008-1 8 1 087 can be used. Among them, the ruthenium compound is preferred from the viewpoint of sensitivity. Examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, and 2,2'-bis(2,3- Dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (for example, JP-A-6-7 5372 and JP-A-6-75 3 73), 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, Japanese Patent Publication No. Sho 48-3 8403 and JP-A-62- Japanese Patent Publication No. 174204 refers to an imidazole compound in which a phenyl group at the 4,4'5,5'-position is substituted with an alkoxycarbonyl group (for example, JP-A-7-10913). Preferred is 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)- 4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,4-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole. Examples of the alkylphenone compound include diethoxyacetophenone and 2-methyl-2-morpholino-1-(4-methylsulfonylphenyl)propan-1-one. 2-Dimethylamino-1-(4-morpholinophenyl)-2-benzylidenebutan-1-one, 2-dimethylamino-1-(4-morpholinophenyl) )-2-(4-methylphenylmethyl)butan-1-one, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethylketal, 2 -hydroxy-2-methyl-1-[4-(2.hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1- (4-iso-43-201232174 acryloylphenyl)propane-ι·ketone oligomer, etc., preferably ΐ 2-morpholino-1-(4-methylsulfonylphenyl)propane-n 1-(4-morpholinophenyl)-2-benzylbutan-1-one Irgacure 369, 907 (above, BASF Japan 5) As the triazine compound, 2,4-bis ( (4. methoxyphenyl)-1,3,5-triazine, 2,4-bis(tris4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis ( Trichloro-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-yl)-1,3,5-triazine, 2,4-bis(trichloromethane) -6-(an-2-yl) Vinyl]-1,3,5-triazine, 2,4-bis(tris-2-(furan-2-yl)vinyl]·1,3,5-triazine, 2,4 )-6-[ 2. (4-Diethylamino-2-methylphenyl) oxazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dienyl)- 1,3,5-triazine, etc. As the starting agent of the mercaptophosphine oxide, a benzamidine diphenylphosphine oxide or the like can be used. A commercially available product such as Irgacu Japan Co., Ltd. can be used. , which may be N-benzylidenesulfonylphenyl)butan-1-one-2-imine, N-phenyltolylsulfonylphenyl)octane-1-one-2-imine , N-ethyl-6-(2-methylbenzhydryl)-9H-carbazolyl-3-yl, N-acetoxy-1-[9-ethyl-6-{2-methyl- 4 (3, dioxocyclopentylmethoxy)benzimidyl}-9H-carbazole 3 2- 2-methyl-seeking, 2-dimethylamine, etc. Tractor trichloromethyl)-6-chloromethyl)-6-(methyl)-6-piperidine-methoxystyrene 2-(5-methylfurochloromethyl)-6-[ • double ( Trichloromethyl ketone-1,3,5-trimethoxyphenyl)ethyl 2,4,6-trimethyl re 819 (Ciba. oxy-1 - (4-benzoquinone) Base-1 - (4-acid-1-[9-ethane]ethane-1-imine, 3-dimethyl-2,4-S-3-yl]ethane--44 - 201232174 1- Imine and the like. Commercial products such as Irgacure OXE-Ol, ΟΧΕ-02 (above, manufactured by BASF Japan), and N-1919 (made by ADEKA) can be used. Further, as the polymerization initiator (D), benzoin such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether or benzoin isobutyl ether may be mentioned. a compound; benzophenone, methyl benzoyl benzoyl benzoate, 4-phenyl benzophenone, 4-benzylidene-4'-methyldiphenyl sulfide, 3,3', a benzophenone compound such as 4,4'-tetra(t-butylperoxycarbonyl)benzophenone or 2,4,6-trimethylbenzophenone; 9,10-phenanthrenequinone, 2-B Anthraquinone compounds such as guanidine and camphor; 10 _ butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, titanocene compound, and the like. These may be preferably used in combination with a polymerization initiation aid (D 1 ) (particularly an amine) described later. It may also contain a polymerization initiation aid (D1). The polymerization initiation aid (D1) can be used in combination with the polymerization initiator (D), which is a compound or a sensitizer used to promote polymerization of a polymerizable compound which starts polymerization by a polymerization initiator. Examples of the polymerization initiation assistant (D1) include an amine compound, a thiazolium compound, an alkoxyfluorene compound, a thioxanthone compound, and a carboxylic acid compound, and examples thereof include an amine compound, and triethanolamine and methyldiethanolamine are mentioned. , triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethyl benzoate Aminoethyl, 4-dimethylaminobenzoic acid 2-ethylhexyl, N,N-dimethyl-p-aniline, 4,4'-bis(dimethylamino)benzophenone, - 45- 201232174 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(ethylmethylamino)benzophenone, etc., of which 4,4'-double (Diethylamino)benzophenone is preferred. It is also possible to use EAB-F (Buddha Valley Chemical Industry Co., Ltd.) and other sales items. The thiazoline compound may, for example, be a compound represented by the formula (ΠΙ-1) to the formula (III-3).

The alkoxy ruthenium compound may, for example, be 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene or 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, and 1- Chloro-4-propoxythioxanthone and the like. Examples of the carboxylic acid compound include phenylsulfonyl acetic acid, methylphenylsulfonyl acetic acid, ethyl phenylsulfonyl acetic acid, methyl ethyl phenylsulfonyl-46 - 201232174 acetic acid, and dimethyl Phenyl sulfonyl acetic acid, methoxyphenylsulfonyl acetic acid, dimethoxyphenylsulfonyl acetic acid, chlorophenylsulfonyl acetic acid, dichlorophenylsulfonyl acetic acid, N-phenyl Glycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthyloxyacetic acid, and the like. The content of the polymerization initiator (D) is preferably from 0.1 to 40 parts by mass, more preferably from 1 to 30 parts by mass, per 100 parts by mass of the total of the resin (B) and the polymerizable compound (C). When the content of the polymerization initiator (D) is within this range, the pattern can be formed with high sensitivity, and the chemical resistance, mechanical strength, and surface smoothness of the pattern tend to be improved. When the polymerization start-up aid (D1) is used, the amount of the resin (B) and the polymerizable compound (C) is preferably 0.01 to 50 parts by mass, more preferably 0.1 part by mass. ~40 parts by mass. Further, each polymerization initiator (D) is 1 mole, preferably 〇.〇1 to 1 〇mol, more preferably 0.01 to 5 moles. When the amount of the polymerization initiation aid (D1) is within this range, the pattern can be further formed under high sensitivity, and the pattern productivity tends to be improved. Further, the colored photosensitive resin composition of the present invention may further contain a polyfunctional thiol compound (T). The polyfunctional thiol compound (T) is a compound having two or more sulfonyl groups in the molecule. Further, when a compound having two or more sulfonyl groups adjacent to an aliphatic hydrocarbon group is used, a pattern can be formed with high sensitivity, which is preferable. , 3 diethanol oxime ethyl thio bis, styrene diol sulfonate diester 3- hexane acid { 丁 乙 参 、 基 基 基 基 基 基 基 基 基 & & & & & & & & & & & & & 羟 羟 羟 羟 羟 羟 羟 羟Expanded di-tribasic alcohol, methylenedi-C alkyl ester bis-butyric acid sulfur 4-, acetamidine, A mesh 1 N1/base, ester oxime polyol acid is expanded to thiopropyl 3- as a dibasic { Alkane bis- sulfonate-47- 201232174 acid ester), butanediol bis(3-sulfonylpropionate), trimethylolpropane ginseng (3-sulfonylpropionate), trishydroxyl Propane ginseng (3-sulfonyl acetate), pentaerythritol bismuth (3-sulfonyl propionate), pentaerythritol bismuth (3-sulfonyl acetate), hydroxyethyl ginseng (3-sulfonate) Propionate), pentaerythritol oxime (3-sulfonylbutyrate), 1,4-bis(3-sulfonylbutoxy)butane, and the like. The content of the polyfunctional 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 polyfunctional thiol compound (T) is within this range, the sensitivity tends to be high, and the developability tends to be good. The solvent (E) is not particularly limited, and a solvent generally used in the field can be used. For example, an ether solvent (solvent containing -COO- in the molecule, a solvent not containing ruthenium), an ether solvent other than the ester solvent (a solvent containing -〇-, not containing -COO· in the molecule), or an ether ester solvent can be used ( a solvent containing -COO- and -〇- in the molecule), a ketone solvent other than an ester solvent (a solvent containing -CO- in the molecule, a solvent not containing -coo-), an alcohol solvent, an aromatic hydrocarbon solvent, a guanamine solvent, and Methyl Yafeng. These solvents may be used alone or in combination of two or more kinds. Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl acetate, 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. -48- 201232174 Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, and diethylene glycol monomethyl. Ether, diethylene 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-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, two Ethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenethyl ether, methyl anisole, and the like. Examples of the ether ester solvent include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, and 3-methoxypropionic acid. Methyl ester, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, 2-methoxypropionic acid Ethyl ester, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, 2- Ethyl ethoxy-2-methylpropionate, 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, 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-pentyl Ketone, cyclopentanone, cyclohexanone, isophorone and the like. Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin. -49- 201232174 Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, and mesitylene. The guanamine solvent may, for example, be N,N-dimethylformamide, N,N-dimethylacetamide or N-methylpyrrolidone. Among the above solvents, from the viewpoint of coatability and drying properties, an organic solvent having a boiling point of from 1 m ° C to 180 ° C or less is preferred. Among them, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, and the like are preferred. The content of the solvent (E) is preferably from 60 to 95% by mass, more preferably from 70 to 90% by mass, based on the total amount of the photosensitive resin composition. In other words, the solid content of the colored photosensitive resin composition is preferably from 5 to 40% by mass, more preferably from 1 to 30% by mass. When the content of the solvent (E) is within the above range, the flatness at the time of coating tends to be good. The colored photosensitive resin composition of the present invention preferably contains a surfactant (F). The surfactant may, for example, be a polyfluorene-based surfactant, a fluorine-based surfactant, or a polyfluorene-based surfactant having a fluorine atom. When the surfactant is contained, the flatness at the time of coating tends to be good. 〇 As the polyoxynene surfactant, an interface having a decane bond can be mentioned. Specific examples thereof include Toray polyoxygen DC3PA, same SH7PA, same DC11PA, same SH21PA, same SH28PA, same SH29PA, same SH30PA, and polyether modified polyoxyxene SH8400 (trade name: Toray. Dow Corning). KP321, KP322, KP323, KP324, KP326, KP340, KP341 (Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, -50- 201232174 TSF4445, TSF-4446, TSF4452, TSF4460 (Momentive Performance Materials 'Japan contract company system) and so on. The fluorine-based surfactant is a surfactant having a fluorocarbon chain. Specifically, Furorina (registered trademark) FC430, FC431 (Sumitomo 3M (share) system), megafac (registered trademark) F142D, F171, F172, F173, F177, F183, R30 (DIC) )), f-top (registered trademark) EF301, EF3 03, EF351, EF 3 5 2 (Mitssubishi Materials Corporation), Surflon (registered trademark) S381, same as S382, same as SC101 It is the same as SC105 (Asahi Glass Co., Ltd.) and E5 84 4 (manufactured by Daikin Fine Chemical Research Institute). Examples of the polyfluorene-based surfactant having a fluorine atom include a surfactant having a siloxane chain and a fluorocarbon chain. Specific examples include megafac (registered trademark) R〇8, the same BL20, the same F475, the same F477, and the same F443 (DIC system). Preferably, the megafac (registered trademark) F475 ° surfactant (F) is 0.001% by mass or more and more preferably 0.02% by mass or more based on the total amount of the colored photosensitive resin composition of the present invention. · 1% by mass or less, more preferably 0.01% by mass or more and 0.05% by mass or less. When the surfactant is contained in this range, the flatness of the coating film can be improved. The colored photosensitive resin composition of the present invention may contain various additives such as a chelating agent, other polymer compound, adhesion promoter, antioxidant, ultraviolet absorber, light stabilizer, and chain shifting agent as necessary. -51 - 201232174 The colored photosensitive resin composition of the present invention ' can be prepared, for example, as follows. First, the pigment of the colorant (A) is mixed with the solvent (E) until the average particle diameter of the pigment is 0. 2 μm or less, and is dispersed by using a bead mill or the like. At this time, a part or all of the pigment dispersant and the resin (B) may be added as necessary. In the obtained pigment dispersion liquid, 'addition of the resin (B), the polymerizable compound (C), the polymerization initiator (D), and other components used as necessary, and further adding the necessary additional solvent to the predetermined concentration, A colored photosensitive resin composition for the purpose can be obtained. The colored photosensitive resin composition of the present invention is processed in a color filter by, for example, the steps shown in the following (1) to (4). (1) a step of applying a colored photosensitive resin composition of the present invention to a substrate to obtain a coating film (2) a step of exposing the coating film to a coating film after exposure to a coating film (3) After the exposure, the coating film is imaged in an alkali developing solution to obtain a pattern (4). The step of obtaining a hardened pattern by baking the pattern is used as a method for obtaining a pattern, and light can be cited. Etching method, spraying method, printing method, and the like. Among them, photolithography is also preferred. The photolithography method is a method in which the colored photosensitive resin composition is applied onto a substrate, dried, and exposed by a photomask to obtain a pattern by development. Examples of the substrate include glass, metal, and plastic, and may be in the form of a plate or a film. -52- 201232174 Examples of the plastic material include polyolefins such as polyethylene, polypropylene, and decene-based polymers, polyvinyl alcohol, polyethylene terephthalate, polyethylene naphthalate, and poly (Meth) acrylate, cellulose ester, polycarbonate, polyfluorene, polyether maple, polyether ketone, polyphenylene sulfide, and polyphenylene oxide. The (meth)acrylic acid is at least one selected from the group consisting of acrylic acid and methacrylic acid. A structure such as a color filter, various insulating or conductive films, and a driver circuit can be formed on these substrates. The colored photosensitive resin composition of the present invention is particularly useful in forming a pattern on a plastic substrate because it can be formed in a pattern which is hardened at a low temperature. Examples of the method of applying the substrate include an extrusion coating method, a twin roll coating method, a reverse gravure coating coating method, a CAP coating method, and a slit coating method. Further, an impregnation coater, a roll coater, a bar coater, a spin coater, a slit & spin coater, a slit coater (sometimes referred to as a slit coater, a shower curtain) may be used. Coating is performed by a coating device such as a coater or a spin coater or a spray. Among them, coating by a slit coating, a spin coater, roll coating or the like is also preferred. Examples of the film drying method applied to the substrate include a method of heat drying, natural drying, air drying, and reduced pressure drying. It can also be carried out by combining a plurality of methods. As the drying temperature, it is preferably -120 ° C or more preferably 25 to 100 ° C. Further, as the heating time, it is preferably from 1 sec to 60 minutes, and preferably from 30 seconds to 30 minutes. It is preferred to carry out the drying under reduced pressure to a pressure of 50 to 150 Pa at a temperature of 20 to 25 °C. -53- 201232174 The film thickness of the coating film after drying is not particularly limited, and can be appropriately adjusted by materials, applications, etc., and is generally 〇"~20 μιη, 1~6 μηι 〇 dried coating film Light exposure used to form the target pattern. At this time, the shape of the pattern on the photomask is not particularly limited, and a pattern shape for the purpose of use is used. As the light source used for the exposure, a light source that generates light of 250 to 450 nm is preferable. For example, light of less than 350 nm may be blocked by a filter of a wavelength region, or light of a vicinity of 436 nm, near 3 65 nm may be selectively extracted by using a wavelength filter. . Specific examples thereof include a mercury lamp, a light-emitting device, a metal halide lamp, and a halogen lamp. Preferably, the entire surface of the exposure surface is uniformly irradiated with parallel light, or the correct position of the substrate is to be adjusted, and a mask is used for exposure to expose the aligner, and a lithography machine or the like is preferred. After the exposure, the coating film is brought into contact with the developing solution to dissolve the predetermined portion of the unexposed portion, and a pattern can be obtained by developing the image. As the development, an organic solvent can be used, and the exposed portion of the coating film is swollen in the developing solution to swell, and a pattern having a good shape cannot be obtained, and an alkali compound solution is preferably used. The development method may be either a Pudling process or an immersion fog method. It is preferable to tilt the substrate to an arbitrary angle during development and then perform water washing. Preferably, the shield is used to cooperate with a wavelength blocking the 4 0 8 nm band-pass diode photomask (Mask, for example, a solution, although the water method or the spray of the difficult matter can be -54-201232174 as the alkali Examples of the compound include sodium hydroxide, potassium hydroxide, disodium hydrogen citrate, sodium dihydrogen citrate, diammonium hydrogen citrate, ammonium dihydrogen citrate, potassium dihydrogen citrate, sodium citrate, potassium citrate, sodium carbonate, An inorganic basic compound such as potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, sodium borate, potassium borate or ammonia; and tetramethylammonium hydroxide, 2-hydroxyethyltrimethylammonium hydroxide, monomethylamine, An organic basic compound such as dimethylamine, trimethylamine, monoethylamine, diethylamine, triethylamine, monoisopropylamine, diisopropylamine or ethanolamine. The basic compound is potassium hydroxide, sodium hydrogencarbonate and tetramethyl. The concentration of the basic compound in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass. The aqueous solution of the basic compound may also contain a surfactant. Polyethylene oxide alkane Ether, polyethylene oxide aryl ether, polyethylene oxide alkyl aryl ether, other polyethylene oxide derivatives, oxy-ethyl/oxypropanyl chimeric copolymer, sorbitan fat Acid ester, polyethylene oxide sorbitan fatty acid ester 'polyethylene oxide sorbitol fatty acid ester, glycerin fatty acid ester, polyethylene oxide fatty acid ester, polyethylene oxide alkylamine, etc. Ionic surfactant; sodium lauryl sulfate, sodium oleyl sulfate, sodium lauryl sulfate, ammonium lauryl sulfate, sodium dodecylbenzenesulfonate, sodium dodecyl naphthylsulfonate, etc. a surfactant; and a cationic surfactant such as stearylamine hydrochloride or lauryl trimethylammonium chloride. The concentration of the surfactant in the aqueous solution of the basic compound is preferably 0.01 to 10% by mass. More preferably, it is 5 to 8 mass%, and particularly preferably 〇1 to 5 mass%. -55- 201232174 After further grilling the pattern obtained as described above, a hardened pattern can be obtained. The temperature is 2 5 ° C or more and 2 3 0 ° C or less, preferably 2 5 ° C or more and 200 ° C or less, more preferably 2 5 ° C or more I 60 ° C or less, more preferably 25 ° C or more and 120 ° C or less. The baking time is 1 to 300 minutes, preferably 1 to 180 minutes, more preferably 1 to 60 minutes. In the colored photosensitive resin composition of the invention, a color filter can be produced by repeating the pattern modulation by the above method. The obtained color filter can be provided as a part of the constituent parts on the display device, for example, The liquid crystal display device, the organic EL device, the solid-state imaging device, the electronic paper, and the like are connected to the color image by a known method. [Embodiment] [Embodiment] Hereinafter, the present invention will be described in more detail by way of examples. "%" and "parts" unless otherwise marked, mean % by mass and parts by mass. Synthesis Example 1 An appropriate amount of nitrogen gas was introduced into a beaker having a reflux condenser, a titration funnel, and a stirrer to form a nitrogen atmosphere, and 100 parts of propylene glycol monomethyl ether acetate was placed and heated to 85 °C while stirring. Next, 19 parts of dissolved methacrylic acid and 3,4-epoxytricyclo[5.2.1.02.6]decyl acrylate (the compound represented by the formula (I-1) and the formula (Π) were dropped into the beaker. -1) The compound shown in a molar ratio of 50:50 was mixed with 171 parts of a solution of 40 parts of propylene glycol monomethyl ether acetate, which was dropped over about 5 hours using a drip pump. -56- 201232174 On the other hand, a solution of 26 parts of 2,2'-azobis(2,4-dimethylvaleronitrile) 2 parts of propylene glycol monomethyl ether acetate dissolved in a polymerization initiator was used. Another drop into the pump was dropped into the beaker for about 5 hours. After the completion of the dropwise addition of the polymerization initiator, the mixture was kept at the same temperature for about 3 hours, and then cooled to room temperature to obtain a resin solution Ba having a solid content of 43.5% and an acid value of 53 mgKOH/g (in terms of solid content). The obtained resin Ba had a weight average molecular weight Mw of 8,000 and a molecular weight distribution (Mw/Mn) of 1.98. Synthesis Example 2 In a beaker equipped with a stirrer, a thermometer, a reflux cooling tube, a titration funnel, and a nitrogen introduction tube, 123 g of propylene glycol monomethyl ether acetate was introduced, and the atmosphere inside the beaker was changed from nitrogen to nitrogen, and then the temperature was raised to 100 ° C. After that, it will be 72.6 g (0.41 mol) of benzyl methacrylate, 42. g of methacrylic acid (0.49 mol), and a monomethacrylate of tricyclodecane skeleton (manufactured by Hitachi Chemical Co., Ltd.). FA-513M) A solution of 3.6 g of azobisisobutyronitrile was added to a mixture of 23.0 g (0.10 mol) and propylene glycol monomethyl ether acetate (137 g), and the mixture was dropped into a beaker for 2 hours from a titration funnel. In 丨〇 (Γ (: continue for 5 hours of stirring. Secondly, change the environment inside the beaker from nitrogen to air, epoxy methacrylate 21.3g [0.15 mol, (for the methyl group used in this reaction) The carboxyl group of acrylic acid was 31 mol%), 0.9 g of trimethylaminomethylphenol and 0_145 g of hydroquinone were placed in a beaker, and the reaction was continued at Π ° C for 6 hours to obtain a solid component of 38.3%, @胃120.1 MgKOH/g (solid content conversion) resin solution Bb. The weight average molecular weight in terms of ethylene was 1 〇, 5 〇〇, and the sub-57-201232174 sub-quantity distribution (Mw/Mn) was 2.1. Synthesis Example 3 was equipped with a stirrer, a thermometer, a reflux cooling tube, a titration funnel, and a nitrogen introduction tube. In the beaker, 125.lg of propylene glycol monomethyl ether acetate was introduced, and the atmosphere in the beaker was changed from nitrogen to nitrogen. After heating to 100 ° C, 96.0 g (0.55 m) of benzyl methacrylate was added. 30.6 g (0.36 mol) of methacrylic acid, monomethacrylate of tricyclodecane skeleton (FA-513M manufactured by Hitachi Chemical Co., Ltd.) 22.0 g (0.10 mol) and propylene glycol monomethyl ether acetate 149 g of the resulting mixture was added with a solution of 3.6 g of azobisisobutyronitrile, and the mixture was dropped into a beaker over 2 hours from the titration funnel, and further stirred at 5 °C for 5 hours. Next, the atmosphere in the beaker was changed from nitrogen to air. Epoxypropyl methacrylate 21.3 g [0.15 mol, (42 mol% for the carboxyl group of methacrylic acid used in the present reaction)], dimethylaminomethylphenol quinone. 9 g and hydrogen醌 0.145g was placed in a beaker, and the reaction was continued at 1 l ° C for 6 hours to obtain a solid. A resin solution Be of 37.8% and an acid value of 67.7 mgKOH/g (in terms of solid content). The polystyrene-equivalent weight average molecular weight measured by GPC was 9,400, and the molecular weight distribution (Mw/Mn) was 2.0. Nitrogen was introduced into a nitrogen atmosphere at a flow rate of 0.02 L/min in a beaker equipped with a reflux condenser, a titration funnel, and a stirrer, and 200 parts of 3-methoxy-1-butanol and 3-methoxybutylacetic acid were placed. 100 parts of the ester, while stirring, heated from -58 to 201232174 to 70 °C. Next, '54 parts of methacrylic acid, 3,4-epoxytricyclo [5.2.1.02 6] mercapto acrylate (the compound represented by the formula (1-1) and the compound represented by the formula (II-1)) 180 parts of molar ratio of 50:50) 180 parts and 67 parts of N-cyclohexylmaleimide dissolved in 140 parts of 3-methoxy-1-butanol to prepare a solution, and the solution was dropped into it. The pump was dropped into a beaker at 70 ° C for 4 hours. On the other hand, 20 parts of the polymerization initiator 2,2'-azobis(2,4-dimethylvaleronitrile) was dissolved in a solution of 240 parts of 3-methoxybutyl acetate, and another solution was used. Drop into the pump and drip into the beaker over 4 hours. The solution of the polymerization initiator was kept at 70 ° C for 4 hours after the completion of the dropwise addition, and then cooled to room temperature to obtain a solution of a resin component Bd having a solid content of 32.6% and a solution acid value of 34.3 mg-KOH/g. The obtained resin Bd had a weight average molecular weight Mw of 9000 and a molecular weight distribution (Mw/Mn) of

Synthesis Example 5 In a beaker equipped with a stirrer, a thermometer, a reflux condenser, a titration funnel, and a gas introduction tube, 250 parts of propylene glycol monomethyl ether acetate was introduced. Thereafter, nitrogen gas was introduced into the beaker using a gas introduction pipe, and the atmosphere inside the beaker was replaced by nitrogen gas. Thereafter, after raising the temperature in the beaker to 100 ° C, 152.6 parts of benzyl methacrylate, 41.7 parts of methacrylic acid, 1.5 parts of azobisisobutyronitrile, and propylene glycol monomethyl ether acetate were added. 150 parts of the resulting mixture was dropped into the beaker using a titration funnel over 2 hours, and after the completion of the dropwise addition, -59-201232174, further at 10 (TC was continued for 2.5 hours, and the weight average molecular weight Mw was 2·3χ104, and the solid content was 34. %, a resin solution of a solution acid value of 47 mg-KOH/g Be. The weight average molecular weight (Mw) and the number average molecular weight (?n) of the resin obtained in the synthesis example were measured by the GPC method under the following conditions; Κ 2479 (( Stock) Shimadzu Manufacturing Co., Ltd.)

Pipe string; SHIMADZU Shim-pack GPC-80M

Column temperature; 40 ° C solvent; THF (tetrahydrofuran) flow rate; 1 · OmL / min detector; Ri The polystyrene-converted ratio of weight average molecular weight and number average molecular weight (Mw / Mn) obtained above as molecular weight distribution . Example 1 [Preparation of coloring photosensitive resin composition 1] Mixed pigment; CI color red 1 7 7 49 parts of polyester-based pigment dispersant 16 parts of resin solution Be 29 parts of propylene glycol monomethyl ether acetate 280 parts, used Bead mill fully disperse pigment pigment dispersion A, mixed -60- 201232174 Pigment: c_l. Pigment red 254 5.9 parts acrylic pigment dispersant 2.2 parts resin solution Be 4.9 parts propylene glycol monomethyl ether acetate 29 parts, use Pigment dispersion liquid B of the pigment which is sufficiently dispersed in the bead mill, mixed resin (B1): 126 parts of resin solution Ba, resin (B2): 72 parts of resin solution Bb, polymerizable compound: dipentaerythritol hexaacrylate (KAYARAD DPHA; Japan Chemicals (stock) system 63 parts, polymerization initiator: N-benzylidene-1-(4-phenylsulfonylphenyl) xinyuan-1-one-2-imine (IrgacureOXE- Ol; BASFJapan Co., Ltd.) 9.4 parts, solvent: 313 parts of propylene glycol monomethyl ether acetate, and surfactant: polyether-denatured polysiloxane (Toray polyoxo SH8400; Toray Dow Corning Co., Ltd.) 0.02 parts, Coloring sensitivity 1 lipid composition. Example 2 [Preparation of coloring photosensitive resin composition 2] Mixed pigment: CI pigment yellow 139 18 parts of polyester-based pigment dispersant 7.2 parts of resin solution Be 13 parts - 61 - 201232174 Propylene glycol monomethyl ether acetate 116 parts , using a bead mill to fully disperse the pigment dispersion A of the pigment, mixed pigment: CI pigment red 1 77 72 parts polyester pigment dispersant 20 parts resin solution Be 61 parts propylene glycol monomethyl ether acetate 310 parts, using beads The pigment dispersion dispersion B of the pigment is sufficiently dispersed in the mill, the mixed resin (B1): resin solution Ba 90 parts, resin (B2): resin solution Be 78 parts, polymerizable compound: dipentaerythritol hexaacrylate (KAYARAD DPHA; Nippon Chemical (Stock) 40 parts, polymerization initiator: N-benzylideneoxy-1-(4-phenylsulfonylphenyl) octane-1-one-2-imine (Irgacure OXE-Ol; 8.1 parts, solvent: propylene glycol monomethyl ether acetate 165 parts, and surfactant: polyether modified polyoxylized oil (Toray polyoxyl SH8400; TorayDowCorning (manufactured by Toray) Co., Ltd.) 0.02 parts, coloring Photosensitive resin composition 2. Example 3 [Preparation of coloring photosensitive resin composition 3] Mixing -62 - 201232174 Pigment: CI coloring red 254 5 1 part of polyester-based pigment dispersing agent 1 part of propylene glycol monomethyl ether acetate 287 parts, using beads After the mill sufficiently disperses the pigment dispersion of the pigment, the resin (B1) is mixed: resin solution Ba 184 parts of resin (B2): resin solution Bb 50 parts of polymerizable compound: dipentaerythritol hexaacrylate (KAYARAD DPHA; Nippon Chemical Co., Ltd. ))) 64 parts of polymerization initiator: N-benzylideneoxy-1-(4-phenylsulfonylphenyl) xinyuan-1-one-2-imine (Irgacure OXE-Ol; manufactured by BASF Japan 13 parts of solvent: propylene glycol monomethyl ether acetate 336 parts of surfactant: polyether-denatured polysiloxane (Toray polyoxyl SH8400; manufactured by Toray Dow Corning Co., Ltd.) 0.02 parts to obtain a colored photosensitive resin composition 3 . Example 4 [Preparation of Colored Photosensitive Resin Composition 4] Mixed Pigment: CI Pigment Green 36 14 parts of polyester-based pigment dispersant 2.7 parts of resin solution Be 4.0 parts of propylene glycol monomethyl ether acetate 56 parts, using bead mill Machine to fully disperse pigment pigment dispersion A, -63- 201232174 Mixed pigment: CI pigment yellow 138 12 parts polyester pigment dispersant 2.5 parts resin solution B e 1.9 parts propylene glycol monomethyl ether acetate 66 parts using bead mill The pigment dispersion liquid B of the pigment is sufficiently dispersed, the mixed resin (B1): 142 parts of the resin solution Ba, the resin (B 2 ): the resin solution B c 4 1 part, the polymerizable compound: dipentaerythritol hexaacrylate (KAYARAD DPHA; Japan Chemical Co., Ltd.) 8 parts, polymerization initiator: N-benzylideneoxy-1-(4-phenylsulfonylphenyl)octane-1-one-2-imine (IrgacureOXE -O 1 ; B ASFJapan Co., Ltd.) 9.6 parts, solvent: propylene glycol monomethyl ether acetate 5 70 parts, and surfactant: polyether denatured polyoxynose oil (Toray polysilica SH8400; TorayDowCorning ) 0.02 parts of 'a colored photosensitive resin composition 4 was obtained. Example 5 [Preparation of coloring photosensitive resin composition 5] Mixed pigment: CI pigment green 58 53 parts Acrylic pigment dispersant 1 1 part - 64 - 201232174 Resin solution Be 62 parts of propylene glycol monomethyl ether acetate 251 parts , using a bead mill to fully disperse the pigment dispersion A of the pigment, mixed pigment: CI·pig yellow 1 3 8 30 parts polyester pigment dispersant 4.4 parts resin solution B e 31 parts propylene glycol monomethyl ether acetate 136 parts The pigment dispersion liquid B of the pigment was sufficiently dispersed using a bead mill, and the mixed resin (B1): resin solution Ba 18 parts, resin (B2): resin solution Bb 147 parts, polymerizable compound: dipentaerythritol hexaacrylate (KAYARAD DPHA; Nippon Chemical Co., Ltd.) 64 parts, polymerization initiator: N-benzylideneoxy-1-(4-phenylsulfonylphenyl) xinyuan-1-one-2-imine (IrgacureOXE -Ol; manufactured by BASF Japan) 13 parts, solvent: propylene glycol monomethyl ether acetate 181 parts, and surfactant: polyether modified polyoxyxide oil (Toray polyoxo SH8400; Toray Dow Corning Co., Ltd.) 0.02 parts The coloring photosensitive resin composition 5 was obtained. Example 6 [Preparation of coloring photosensitive resin composition 6] -65- 201232174 Mixed pigment: cI pigment red 1 77 28 parts of pigment: CI pigment red 254 86 parts of polyester-based pigment dispersant 1 part of resin solution Be 27 parts 403 parts of propylene glycol monomethyl ether acetate, and the pigment dispersion liquid of the pigment is sufficiently dispersed using a bead mill to mix the resin (B1): resin solution Bd 87 parts of resin (B2): resin solution Bb 99 parts of polymerizable compound: dipentaerythritol Hexaacrylate (manufactured by Sakamoto Chemical Co., Ltd.) 3 3 parts polymerization initiator: 2 -methyl-2 - 咐 -1--1-(4-methyl phenylphenyl) propyl -1- Ketone (Irgacure 907; manufactured by BASF Japan) 13 parts of polymerization initiation aid: 4,4'-bis(diethylamino)benzophenone (EAB-F; manufactured by Hodogaya Chemical Industry Co., Ltd.) 7.6 parts solvent : propylene glycol monomethyl ether acetate 294 parts 'to obtain a coloring photosensitive resin composition 6. Comparative Example 1 Preparation of t-colored photosensitive resin composition 7] Mixed pigment: C. I. Pigment red 1 7 7 2 8 parts of pigment: C · I · Pigment red 2 5 4 8 6 parts of polyester-based pigment dispersant 1 -份-66- 201232174 Resin solution B e 2 7 parts of propylene glycol monomethyl ether acetate 404 parts, fully dispersed pigment pigment dispersion using a bead mill, mixed resin: resin solution Bd 169 parts of polymerizable compound: Dipentaerythritol hexaacrylate (manufactured by Sakamoto Chemical Co., Ltd.) 32 parts polymerization initiator: 2-methyl-2-morpholino-1-(4-methylsulfonylphenyl) propyl hospital-1 - 嗣 (Irgacure 907; manufactured by BASF Japan) 12 parts of polymerization initiation aid: 4,4'-bis(diethylamino)benzophenone (EAB-F; manufactured by Hodogaya Chemical Industry Co., Ltd.) 7.4 parts Solvent: propylene glycol monomethyl ether acetate 92 parts of 3-methoxy-1-butanol 67 parts of 3-methoxybutyl acetate 67 parts, and the colored photosensitive resin composition 7 was obtained. <Production of Patterns> A PET film (LUMIRROR 75-T60 manufactured by Toray) was bonded to a square glass plate having a side length of 2 inches to prepare a substrate. The colored photosensitive resin composition was applied onto the PET film side of the substrate by a spin coating method, and preheated at 60 ° C for 2 minutes on a hot plate. After cooling, the substrate coated with the colored photosensitive resin composition was placed at a distance of 150 μm from the mask made of quartz glass, and exposed to 150 mJ/cm 2 in an atmosphere using an exposure machine (TME-150RSK; T0PC0N (manufactured by T0PCN)). The amount (365 nm reference) was irradiated with light. Also, as the photomask, a line of 10 to 100 Km and a pattern of -67 to 201232174 are used. After being irradiated with light, it was immersed in a water-based developing solution containing 0.12% of a nonionic surfactant and potassium hydroxide 〇·0.4% at 40 ° C for immersion, and then washed with pure water. Net formation pattern. The film thickness of the obtained pattern was measured by a film thickness measuring device (DEKTAK3; manufactured by Nippon Vacuum Technology Co., Ltd.) and found to be 2 μm. The pattern formed in the same manner as described above was further heated at 50 ° C for 5 minutes (post-grilling) to obtain a hardened pattern. Further, the pattern formed in the same manner as described above was further heated at 100 ° C for 5 minutes (post-grilling) to obtain a cured pattern. The film thickness of the obtained cured pattern was measured in the same manner as above, and was 2 μm. <Evaluation of Solvent Resistance> On the pattern formed on the substrate, 1 ml of propylene glycol monomethyl ether acetate was dropped, and after standing for 30 seconds, the spin coater was used for 10 seconds at 1000 rpm. Turn to remove the propylene glycol monomethyl ether acetate on the pattern. The film thickness retention ratio was calculated from the film thickness measured before and after the contact with propylene glycol monomethyl ether acetate by the following formula. The higher the film thickness retention rate, the better the hardenability, and the color mixing can be prevented when the color filter is produced. The results are shown in Table 1. (film thickness retention ratio) (%) == (film thickness after contact) / (film thickness before contact) <resolution evaluation> -68- 201232174 The resulting pattern is a laser micromirror (Axio Imager MAT Carl) Observed by Zeiss, the minimum size of the solution is taken as the resolution. The higher the resolution, the finer the color filter can be produced. The results are shown in Table 1. [Table 1] Example 1 Example 2 Example 3 Example 4· Example 5 Example 6 Comparative example baking temperature coloring photosensitive resin composition 1 2 3 4 5 6 7 No resolution ("m) 10 2 0 2 0 2 0 2 0 3 0 4 0 Film thickness retention (%) 9 0 9 0 9 7 9 0 9 8 9 0 8 7 5 03⁄4 Resolution (“ m) 10 2 0 2 0 2 0 2 0 3 0 4〇 Film thickness retention rate (%) 9 2 9 1 9 7 9: 1 9 8 9 0 8 8 10 03⁄4 Resolution (/1 m) 10 2 0 2 0 2 0 2 0 3 0 4 0 Film thickness retention rate ( %) 9 2 9 2 9 7 9 2 9 8 9 1 8 7 The pattern formed using the colored photosensitive resin composition of the example was confirmed to have excellent resolution. Further, even if it was not subjected to a high temperature of more than 200 t In the case of the baking step, it was confirmed that the solvent resistance was excellent. It was found that a high-definition and high-quality color filter can be obtained by using a substrate having low heat resistance. A coloring photosensitive resin composition is used to obtain a pattern with high resolution and a high-quality color filter. -69-

Claims (1)

201232174 VII. Patent application scope: 1 · A coloring photosensitive resin composition characterized by containing (A), (Bl), (B2), (C), (D) and (E), wherein (A) (B1) containing at least one structural unit selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides, monomers derived from cyclic ethers having 2 to 4 carbon atoms, and ethylenically unsaturated bonds a copolymer of structural units (but no ethylenically unsaturated bonds in the side chain); (B2) a resin having an ethylenically unsaturated bond in the side chain; (C) a polymerizable compound; (D) a polymerization initiator (E) solvent. 2. The colored photosensitive resin composition of claim 1, wherein (B2) is a resin obtained by copolymerizing the copolymers obtained in the following (a) and (c) and further reacting with (b), Wherein (a): at least one selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides; (b) : a monomer having a cyclic ether having 2 to 4 carbon atoms and an ethylenically unsaturated bond; ): a monomer having an unsaturated bond capable of copolymerizing (a) and (b). 3. The colored photosensitive resin composition according to item 1 or item 2 of the patent application, wherein the content of (B1) is 1% by mass or more based on the total amount of (B1) and (B2). Below mass%. -70-201232174 4. A pattern 'characterized by a colored photosensitive resin composition as in the first aspect of the patent application. A color filter </ RTI> is characterized by containing a pattern as in item 4 of the patent application. 6. A method of producing a color filter, comprising the steps of (1) to (4) below, (1) by any one of items 1 to 3 of the patent application scope a step of coating a photosensitive resin composition onto a substrate to obtain a coating film; (2) a step of obtaining a film after exposure by exposing the coating film to the mask; (3) a step of developing a post-exposure coating film on an alkali developing solution to obtain a pattern; (4) a step of obtaining a cured pattern by baking the pattern. 7. The method of producing a color filter according to claim 6, wherein the step (4) is a step of baking at a temperature of 25 ° C or more and 1 20 ° C or less. 8. The method of producing a color filter according to claim 6 or 7, wherein the substrate in the step (1) is a plastic substrate. -71 - 201232174 Four designated representatives: (1) The representative representative of the case is: No (2) The symbol of the representative figure is a simple description: No 201232174 If there is a chemical formula in the case, please disclose the chemical formula that best shows the characteristics of the invention: None -4-