TW200937116A - Colored photosensitive resin composition - Google Patents

Abstract

The present invention provides a colored photosensitive resin composition comprising colorant (A), binder resin (B), photopolymerizable compound (C), photopolymerization initiator (D) and solvent (F), wherein colorant (A) is a colorant containing a compound represented by formula (A-I): [in formula (A-I), R1 to R18 each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a straight or branched alkyl group having 1 to 5 carbon atoms, a nitro group, a phenyl group, -SO2NHR21 or -COOR21; R21 represents a hydrogen atom, an aliphatic hydrocarbon group having 1 to 8 carbon atoms, a cyclohexyl group, an alkylcyclohexyl group wherein the alkyl moiety has 1 to 4 carbon atoms, an alkoxyalkyl group having 2 to 15 carbon atoms, -R31-CO-O-R32, -R31-O-CO-R32, or an aralkyl group having 7 to 10 carbon atoms; R31 represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms, R32 represents a monovalent aliphatic hydrocarbon group having 1 to 8 carbon atoms; R19 and R20 each independently represents a hydrogen atom, a methyl group, an ethyl group or an amino group; M represents Cr or Co; D represents a hydrogen atom, a monovalent metal cation or a monovalent cation of a compound having a xanthene skeleton].

Description

200937116 VI. Description of the Invention: [Technical Field of the Invention] The present invention relates to a coloring photosensitive resin composition and the like. · [Prior Art]

As a coloring agent in the coloring photosensitive resin composition, it is known to use a dye for the contrast of the color filter and the light sheet of the Tyran. For example, in Patent Document 1 to be described later, a colored photosensitive resin composition containing VALIF AST Red 1308 or VALIFAST Red 1306 as a dye is disclosed. [Patent Document 1] JP-A-2003-295427 [Summary of the Invention] However, it is known that there is room for improvement in contrast in color filters formed using a colored photosensitive resin composition containing a conventional dye. . The inventors of the present invention have found that the color-sensitive photosensitive resin composition containing a certain compound can be provided with a color filter having a high contrast ratio in order to find a color-sensitive photosensitive resin composition which can solve the above-mentioned problems. That is, the present invention is a color-sensitive photosensitive resin composition containing a toner (A), a binder resin (B), a photopolymerizable compound (C), and a photopolymerization initiator (D). And a solvent, wherein the colorant is a coloring agent containing a compound represented by the formula (A-Ι): 6 320834 200937116

典 L ΛΛ ΛΛ i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i Base, 2, _21 or -C00R'· burnt base, lining hydrocarbon group of Wei 1 to 8, cyclohexyl group, aryl group; c〇m—, or carbon number 7 to 1 (❹ to up to 8) An aliphatic hydrocarbon group, R32 represents a monovalent aliphatic hydrocarbon group having a carbon number of 1 罾 to 8; 咴1 1 R and R 2 ° are each independently represented by chlorine, Μ represents dC〇; Μ ethyl or amine group; D represents a hydrogen atom, a monovalent metal cation or a valence cation of a compound having a xanthene backbone. The X' of the colored photosensitive resin composition resin (B) of the present invention is a resin having a polymerizable unsaturated bond in a side chain. In the above-mentioned colored photosensitive resin composition of the present invention, a cross-linking enhancer (E) is further provided in the coloring photosensitive resin composition of the present invention. Is a compound containing an epoxy group. Further, the present invention is a color filter containing the above colored photosensitive resin Further, the present invention is a use of the above colored photosensitive resin composition for producing a color filter. Further, the present invention is a formula (A-Ι). The use of the compound to produce a colored photosensitive resin composition:

The formula [H (H), the middle of 'R1 to R18) are independent, and represent a hydrogen atom, a fluorine atom, a gas atom, an atom, a linear or branched carbon group having 1 to 5 carbon atoms, an exact group, a phenyl group. (10) r21; represents a hydrogen atom, an aliphatic hydrocarbon group having 1 to 8 carbon atoms, a cyclohexyl group, a decylcyclohexyl group having 1 to 4 carbon atoms, a KCch)_r32 having a carbon number of 2 to 15, and a R31_〇_c 〇_R32, or a quaternary alkyl group having 7 to 1 fluorene; 'R32 represents a carbon number 1 R represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms to a monovalent aliphatic hydrocarbon group of 8; 320834 8 200937116 * R and _ only 2° are independent, representing a hydrogen atom, a methyl group, an ethyl group or an amine group; Μ represents Cr or Co; ^ D represents a hydrogen atom, a monovalent metal cation or a compound having a compound of a xanthene backbone. Valence cation]. [Embodiment] The coloring photosensitive resin composition of the present invention contains a coloring agent (A), and the coloring agent (4) is composed of a compound represented by (A-Ι). The colored photosensitive resin composition is used to produce a color filter, and the compound represented by the formula ρ-ι) is used to produce a colored photosensitive resin composition. R19 R4. 3 Π one

a chlorine atom, a bromine atom, a linear or branched alkyl group having a carbon number of i to 5, a thiol group, a phenyl group, -S02NHR21 or -C00R21; R represents a hydrogen atom, an aliphatic hydrocarbon group having 1 to 8 carbon atoms, a cyclohexyl group, An alkane having a carbon number of 2 to 15 or an alkylcyclohexyl group having a carbon number of 7 to 1 alkyl group of 1 to 4; an oxyalkyl group, -R31-C〇-〇-r32, - R31-〇-c〇-R32, an aralkyl group; R32 represents a carbon number of 1 R31 represents a carbon number of 1 to 8 divalent aliphatic hydrocarbon group 320834 9 200937116 to 8 of a monovalent aliphatic hydrocarbon group; R and ^R2° Each is independent, and means that a hydrogen atom, a methyl group, an ethyl group or an amine group Cr represents Cr or Co; a hydrogen atom, a metal cation of one member, or a monovalent cation having a dielectric complex of a whistling backbone]. As the above aliphatic hydrocarbon group having 1 to 8 carbon atoms, specifically, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, tert-butyl, n-pentyl , n-hexyl, n-heptyl, n-decyl, decyl, methyl butyl, 1,1,3,3-tetramethylbutyl, dimethylhexyl, 16-dimethylheptyl, 2-ethyl Hke and! , 15 5_tetramethylhexyl. As the alkyl group having 1 to 4 carbon atoms as a calcining moiety, a cyclohexyl group, a 2' ethylcyclohexyl group, a 2-n-propylcyclohexyl group, a cyclohexyl group, a 2-n-butylene ring may be mentioned. Hexyl, "cyclohexyl, 4-ethylcyclohexyl, etc.. The alkyl group-based alkoxy group can be exemplified by methoxy group: methoxyethyl group, n-oxy n-propyl group, Methoxy-n-butyl, benzyl-n-pentyl, 1-ethoxy-n-propyl, 2-ethoxypropyl, ethoxypropyl, 2-ethoxyisopropyl, Oxy-n-propyl, ^isopropyl = propyl-propyl, isopropoxy isopropyl, 2-isopropyloxy, propyl-propyl, 3-ethoxy-n-propyl, 3, earth,虱 虱 以 ethoxylated n-propyl, octyloxy-n-hexyl, 3, and 3-(2-ethylhexyloxy) propyl, etc. are preferably propyl, mR32 and n (tetra) 32 (r31 represents carbon number i 320834 10 200937116. A valence aliphatic hydrocarbon group, R32 represents a monovalent aliphatic hydrocarbon group having a carbon number of from 2 to 9 having a carboxyl group, and is dehydrated and has an aliphatic nicotine group of / to 8 The base carbon number is 1. to 1G base, or it has the carbon number of the county. Carbon number 4 has several groups of carbon number 2 to 9 -= === base with ester bond. -R3i-co-(H^& ρ3Ι n butyl dehydration. And waiter 10 is better. (4) The carbon number is 脂肪 / 乍 as the aliphatic hydrocarbon with a carbon number of 2 to 9 in the (10) group, and examples thereof include acetamidine, propionic acid, butyric acid, isobutyric acid, valeric acid, isovaleric acid and caproic acid. , enanthic acid, caprylic acid, t acid, etc., and propionic acid, butyric acid is preferred.% (10) ((4) Qingxin as the aforementioned aliphatic cigarette with a rebellious number 2 to 9 In the base, Kexian is one of the above-mentioned aliphatic hydrocarbons having a carbon number of 2 to 9 to remove i hydrogen atoms. ❿ As an aliphatic hydrocarbon having a carbon number of 1 to 8, it can be enumerated. Methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, second butanol, tert-butanol, n-pentanol, 1-mercapto-n-butanol, 2~甲美正二3乙: Base n-butanol, n-hexanol, n-heptanol, n-octanol, etc. =: B-, n-propanol, isopropanol, n-butanol, isobutanol, second butane tributanol. The number of carbons having a few bases; the month to 8 is an aliphatic hydrocarbon group, Lexon is made up of the above-mentioned aliphatic fumes having a carbon number of 1 to 8 of the radical. The aliphatic hydrocarbon group of the halogen atom is bonded to the aliphatic hydrocarbon group having a carbon number of 1 to 8 of the former 320834 11 200937116 Examples of the carbon number of 4 to 10 having an ester bond obtained by dehydration condensation include, for example, propyl acetate group, butyl acetate group, amyl acetate group, hexyl acetate group, heptyl acetate group, and butyric acid B. Ester group, isopropyl butyrate, butyl butyrate, amyl butyrate, hexyl butyrate, heptyl butyrate, octyl butyrate, decyl valerate, ethyl valerate Base, isopropyl valerate, isobutyl valerate, amyl valerate, hexyl valerate, heptyl valerate, decyl hexanoate, ethyl hexanoate, propyl hexanoate Base, butyl hexanoate, hexyl hexanoate, methyl heptanoate, ethyl heptanoate, isopropyl heptanoate, isobutyl heptanoate, amyl heptanoate, methyl octylate , ethyl octanoate, propyl octyl, isopropyl octyl, butyl octyl, isobutyl octoate, decyl decanoate, ethyl decanoate, propyl citrate, isopropyl citrate ester Etc., with propyl acetate, butyl acetate, ethyl butyrate, butyl butyrate, amyl butyrate, hexyl acetate, methyl valerate, ethyl valerate, pentane The acid isopropyl ester group and the isobutyl valerate group are preferred. Further, in the above aliphatic hydrocarbon group having 2 to 9 carbon atoms of a carboxyl group or an aliphatic hydrocarbon having 2 to 9 carbon atoms having a carboxyl group, the carboxyl group may be substituted with a -C0-C1 group and have a hydroxyl group. The aliphatic hydrocarbon having 1 to 9 carbon atoms or the aliphatic hydrocarbon group having 1 to 9 carbon atoms having a hydroxyl group is subjected to dehydrochlorination condensation to obtain a group having 4 to 10 carbon atoms having an ester bond. Examples of the aralkyl group having 7 to 10 carbon atoms include a benzyl group, a phenethyl group, and a 1-methyl-3-phenylpropyl group. Examples of the monovalent metal cation represented by D include lithium, sodium, and unloading. 12 320834 200937116 As the monovalent cation of the compound having a xanthene skeleton represented by D, a cation represented by the formula (A-II) can be mentioned.

[In the formula (A-II), R22 to R26 are each independently, and represent a halogen atom, an aliphatic hydrocarbon group having 1 to 6 carbon atoms or a substituted aromatic hydrocarbon group having 6 to 10 carbon atoms]. Examples of the aliphatic hydrocarbon group having 1 to 6 carbon atoms include mercapto group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, second butyl group, tert-butyl group, and n-pentyl group. Base, 2-methyl-n-butyl, 3-mercapto-n-butyl, 2,2-dimercaptopropyl, n-hexyl, 2-methyl-n-pentyl, 3-mercapto-n-pentyl, 4- Methyl-n-pentyl, 1,1-didecyl-n-butyl, 1,2-didecyl-n-butyl, 1,3-indenyl-n-butyl, 2,2-didecyl-n-butyl 2,3_Dimercapto-n-butyl, 3,3-dimethyl-n-butyl, 1-ethyl-n-butyl, 2-ethyl-n-butyl, 3-ethyl-n-butyl, 1,1 , 2-trimethyl-n-propyl, 1,2,2-trimethyl-n-propyl, etc., and fluorenyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second Butyl, tert-butyl, n-pentyl and n-hexyl are preferred. Examples of the substituted aromatic hydrocarbon group having 6 to 10 carbon atoms include a phenyl group, an o-nonylphenyl group, a m-nonylphenyl group, a p-tolyl group, a naphthyl group and the like. In the formula (A-Π), R22 to R26 may be arbitrarily combined, and preferred examples thereof include a combination of R22 and R24 being a hydrogen atom, R23 and R25 being an ethyl group, and R26 being a fluorenyl group; 13 320834 200937116 r22 and R24 is a combination of a hydrogen atom, an ethyl group, and an ethyl group. The above-mentioned respective substituents and the like may be arbitrarily blended to form a dye of the formula, but among the dyes represented by the formula (H), preferred ones may be those listed.

320834 14 200937116

15 320834 200937116

The content of the colorant (A) is preferably from 25 to 60% by mass, preferably from 27 to 55% by mass, more preferably 30%, based on the mass fraction of the coloring photosensitive resin composition. Up to 50 mass 〇 / 0. When the content of the coloring agent (A) is within the above range, the color density as a color light-passing sheet is sufficient, and since the composition can contain a necessary amount of the binder resin (B), it can be formed into a sufficient mechanical A pattern of strength is preferred. The solid content in the V-color photosensitive resin composition refers to the total amount of the components obtained by removing the solvent contained in the colored photosensitive resin composition. The content of the compound represented by the formula (A-1) in the toner (A) is preferably from 1 〇 to 1 〇〇 by mass, based on the mass fraction (A), preferably 320834. 16 200937116 is 15 to 100% by mass, more preferably 20 to 100% by mass. The colored photosensitive resin composition of the present invention contains a binder resin ^ (B). The above binder resin (B) preferably contains a constituent unit derived from (meth)acrylic acid. Here, (meth)acrylic acid means acrylic acid and/or methacrylic acid. The content of the constituent unit derived from (mercapto)acrylic acid is based on the molar fraction when the total number of moles of the constituent units constituting the binder resin (B) is regarded as 100 mol%. It is preferably 16 to 40 mol%, preferably 18 to 38 mol%. When the content of the structure derived from (meth)acrylic acid is within the above range, the solubility in the non-paraffin portion is good at the time of development, and the residue in the non-paraffin portion after development There is a tendency to not easily remain, so it is better. Examples of the other monomer derived from the constituent unit of the binder resin other than the constituent unit derived from (fluorenyl)acrylic acid include aromatic vinyl compounds, unsaturated acid esters, and unsaturated acid amines. Base alkyl esters, unsaturated carboxylic acid glycidyl esters, vinyl carboxylates, unsaturated oxime ethers, vinyl cyanide compounds, unsaturated guanamines, unsaturated quinones, aliphatic conjugates An alkene, a macromonomer having a monoacryloyl group or a monomethyl propyl group at the terminal of a polymer molecular bond, a compound capable of introducing a polymerizable unsaturated bond in a side chain, or the like. Examples of the compound which can introduce a polymerizable unsaturated bond to the side chain include a compound of the unit represented by the formula (B-I), a compound of the unit of the formula (B-III), and the like. 17 320834 200937116

[In the formula (Β-I) and the formula (Β-III), Ql and (iv) are each independently and represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; ❹

As the binder resin, specifically, for example, mercaptoacrylic acid/methacrylic acid benzyl acetate eupolymer, methyl acrylic acid/methyl acrylic acid benzyl acetate/styrene copolymer, A Propylene methacrylate, methacrylic acid, benzyl acetate, methyl methacrylate, isobornyl vinegar, methacrylic acid/styrene/benzyl methacrylate/N-phenyl malayan Amine copolymer, methacrylic acid / a component represented by formula (BI) (herein, in the formula, Q1 represents a sulfhydryl group, Q2 represents a hydrogen atom) 〆 methacrylate methacrylate copolymer, formula (BI ) a constituent component (herein, in the formula (b_i), y represents a methyl group, Q2 represents a hydrogen atom) / benzyl methacrylate copolymer, methacrylic acid / represented by the formula (B-III) The constituent component (herein, in the formula (Β_ΠΙ), Q1 represents a methyl group, and Q2 represents a hydrogen atom styrene copolymer/tricyclodecyl methacrylate copolymer, etc., preferably: methacrylic acid/ a constituent represented by the formula (Β-Ι) (here, in the formula, Q1 represents a methyl group, Q2 represents a hydrogen atom) / benzyl methacrylate copolymer The constituents represented by the formula (β_Ι;) (here, in the formula (Β-Ι), q represents a methyl group, y represents a ruthenium atom) / methacrylic acid benzyl ester copolymer, methyl propyl Diluted acid / formula (β-ΙΙΙ) shown in the composition (only 'here, in the formula (B - Hj;), q! represents a 320834 18 200937116 base, Q2 represents a hydrogen atom) / styrene copolymer / A When a resin having a polymerizable unsaturated bond is used as the side bond, the obtained coating film tends to have a high solvent property, and therefore it is preferable. The binder resin (B) The acid value is usually from 50 to 150, preferably from 60 to 135, more preferably from 70 to 135. If the acid value is in the above range, the solubility in the developing solution is improved, and the unexposed portion is easily dissolved. In addition, when the image is developed with high sensitivity, the pattern of the exposed portion remains, and the residual film ratio tends to increase, which is preferable. Here, the acid value is required to neutralize the acrylic polymer lg. The measured value of the amount of potassium hydroxide (mg) is usually determined by titration with an aqueous solution of potassium hydroxide. The content of (B) is usually 10 to 35 mass%, preferably 12 to 33 mass%, more preferably 13 to 32 mass%, based on the mass fraction of the solid content of the coloring photosensitive resin composition. When the content of the binder resin (B) is within the above range, a pattern can be formed, and the resolution and the residual film ratio tend to be improved, so that the binder resin having the constituent component represented by the formula (I) is, for example, a constituent component represented by a mercaptoacrylic acid/formula (B-Ι) (herein, in the formula (B-Ι), Q1 represents a sulfhydryl group, Q2 represents a hydrogen atom) / a benzyl methacrylate copolymer, By polymerizing methacrylic acid with benzyl methacrylate to obtain a two-component polymer, and then obtaining the obtained two-component polymer and the compound of the formula (B-Π) (however, here, In B-Π), Q2 represents a ruthenium atom and can be obtained by carrying out a reaction. 19 320834 200937116

构成 methacrylic acid / constitutive component of the formula (Β-ΙΙΙ) (here, in the formula (Β-ΠΙ), Q1 represents a methyl group, Q2 represents a hydrogen atom) / styrene copolymer / methacrylic acid three The cyclic oxime ester copolymer can be obtained by reacting glycidyl methacrylate in a monodecyl acrylate copolymer of benzyl methacrylate, methacrylic acid or tricyclodecane backbone. It. The polystyrene-equivalent weight average molecular weight of the binder resin is usually from 5,000 to 35,000, and preferably from 6,000 to 30,000, more preferably from 7,000 to 28,000. When the weight average molecular weight of the polystyrene is within the above range, the hardness of the coating film is increased, the residual film ratio is also high, and the solubility of the unexposed portion to the developing solution is good, and the resolution tends to be improved. The colored photosensitive resin composition of the present invention contains a photopolymerizable compound (C). The photopolymerizable compound (C) is a compound which can be polymerized by photo-irradiation of the photopolymerization initiator (D) to produce an active radical, an acid or the like, for example, as a polymerizable carbon-carbon unsaturated bond. Compounds and the like. The photopolymerizable compound (C) is preferably a photopolymerizable compound having three or more functional groups. Examples of the trifunctional or higher photopolymerizable compound include pentaerythritol tetraacrylic acid, pentaerythritol tetramethacrylate, dipentaerythritol pentaacrylate, dipentaerythritol pentamethacrylate, dipentaerythritol hexaacrylate, and dipentaerythritol. Mercapto acrylate and the like. The photopolymerizable compound (C) may be used singly or in combination of two or more. 20 320834 200937116 The content of the photopolymerizable compound (c) is preferably from 5 to 90% by mass, preferably from 10 to 80% by mass, based on the mass fraction of the coloring photosensitive resin composition. It is 20 to 70% by mass. When the content of the photopolymerizable compound (C) is within the above range, the coating film is sufficiently cured, the film thickness ratio before and after development is improved, and undercut is less likely to occur in the pattern, and the adhesion tends to be good. Therefore, it is better. The colored photosensitive resin composition of the present invention contains a photopolymerization initiator (D). Examples of the photopolymerization initiator (D) include an acetophenone-based compound, an active radical generator, and an acid generator. Examples of the acetophenone-based compound include diethoxyacetophenone and 2-methyl-2-(N-morpholinyl)-1-(4-methylthiophenyl)propane-1. -ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldidecyl ketal, 2-hydroxy-2-mercapto-1-(4-(2-hydroxyethyl) Oxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-l-[4-(l-methylvinyl)phenyl]propane-1- a ketone oligomer or the like, and 2-methyl-2-(N-indolyl-1-(4-methylthiophenyl)propan-1-one or the like is preferred. The generating agent generates active radicals by light irradiation. Examples of the active radical generating agent include a benzoin-based compound, a benzophenone-based compound, and a Thioxanthone-based compound. A triterpenoid compound, a compound, etc. Examples of the benzoin-based compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzene. Occasionally, isobutyl ether, etc. As the benzophenone compound, for example, benzophenone, 21 320834 200937116 O-Benzene benzoate methyl benzoate, stupid - "η ^ Benxi - Ben _, 4-Benzyl fluorenyl 4-methyl-based sulphide ^": Seven hearts - four ^ flute:: : 丁甘.^. Diphenyl fluorenone, 2, u-trimethyl: benzoyl g^e ^ aryl) As the aforementioned 嗟-based compound, for example, side, 4-isopropyl ketone, 2 s diethyl ketone, & 2 gasified thioxanthone, 1-chloro-4-propoxy thioxanthene, etc. As the above-mentioned triterpenoid compound, for example, 2,4-triazole Methyl)+(4-methoxyphenylindole, .-trione, 2 bis (trimethyl) 〇-6-(4-methoxynaphthyl)- bromo, 2, 4 One pair (tris(4-methoxyphenylethylene)+[2_(5~methylfuran-2-yl)vinyl]-three tillage, 2,4-bis(trichloromethyl)-6-[ 2-(furan-2-yl)vinyl]-1,3,5-triazine, 2,4_bis(tris:base)~6-[2_(4-diethylamino-2-) Ethyl group η, 3, 哄2, 4-bis(dichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1, 3, 5 - Sancha and so on.

Examples of the lanthanoid compound include a ruthenium-based ruthenium-based compound, and specific examples thereof include 1-(4-phenylthio-phenyl)-butane _12_dioxan-2-indole- - benzoate, ι_(4_phenylthio-phenyl)__octane^, diketone 2-indole-quinone-benzoate, ι_(4-phenylthio-phenyl) _ octane-buprole is used in vinegar acetate, 1-(4-phenylthio-phenyl)-butan-1-one oxime-indole-acetic acid. Commercially available products include 〇饨_01 (made by Ciba Specialty Chemicals Co., Ltd.). As the living radical generator other than the above-exemplified ones, for example, 2,4,6-trimethylphenylnonyldiphenylphosphine oxide, 2,2,-bis(o-gas-based) can be used. 4, 4,5,5'-tetraphenyl-1,2,-biimidazole, 10-butyl-2-chloro 22 320834 2〇〇937116 • °Peptone, 2-ethyl hydrazine, hydrazine Benzil, 9, 1 〇 phenanthrenequinone, 樟 know ^, base ketone 1 acid vinegar, titanium titanium (ti tanosene) compounds. * As the above-mentioned acid generator, for example, 4-hydroxy-based dimethyl mirror of p-toluenesulfonic acid, 4-pyridyl phenyl dimethyl hexahydrate, p-benzoquinone 4- Ethyl phenyl dimethyl hydrazine, hexafluoroantimonic acid 4 ethyl phenyl ketone methyl benzyl sulfonate, triphenyl sulfonium p-toluene sulfonate, triphenyl sulfonium hexafluoroantimonate Styrene sulfonic acid diphenyl sulfonium, hexafluoroantimonic acid diphenyl lock and other rust salts, or formazan nitrobenzoate, benzoin toluene ester acid ester. Further, 'the above-mentioned compound as a living radical generating agent' also has a compound which simultaneously generates an acid and an active radical, for example, a triterpenoid photopolymerization initiator, and can also be used as an acid generator. The content of the photopolymerization initiator (D) is preferably from 1.1 to 20% by mass based on the total amount of the binder resin (B) and the photopolymerizable compound (C). It is preferably from 1 to 15% by mass. When the content of the photopolymerization initiator is within the above range, the exposure time can be shortened and productivity can be improved due to high sensitivity, and on the other hand, there is a minimum line width which does not resolve the pattern of the line and the gap due to the sensitivity being too high. It is better to make the line width too thick. The colored photosensitive resin composition of the present invention may also contain photopolymerization starting: masonry (G). The photopolymerization initiation aid (G) is usually a compound which is used in combination with the photopolymerization initiator (D) to promote polymerization of the photocompound (6) which starts polymerization by a photopolymerization initiator. Examples of the alkoxy group of the starting aid (6) include an amine compound, a di% compound, a xanthone compound, and the like. Examples of the amine compound described above include triethanolamine, and A 23 320834 200937116: makeup, diisopropanolamine, methyl 4-di-f-aminobenzoate, and trr-amino-aminobenzoic acid. 4-Dimethylamino benzoic acid isoindole benzoic acid 2-dimethylaminoethyl ester, 4-dimethylamino benzoic acid ketone S|, N'N-dimethyl-p-toluidine , 4,4'-bis (di-f-amino) a stupid (commonly known as michlerone (^^ also 1 dozen, 3^1: 〇)), 4, 4, a double y-ethyl Amino)benzophenone, 4,4, mono-(ethylmethylamino)benzophenone, etc., of which 4, 4,-bis(diethylamino)benzophenone is preferred . Examples of the alkoxy ruthenium compound to be described include, for example, monomethoxy hydrazine, 2-ethyl-9,10-dimethoxy fluorene, 9,1 fluorene diethoxy fluorene, 2-ethyl-9, 10-diethoxyanthracene, and the like. Examples of the thioxanthone-based compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, and 2,4-dichloropyrene. Mocking _, 1-chloro-4-propoxy oxime ketone and the like. The photopolymerization initiation aid (G) may be used singly or in combination of two or more. In the meantime, the commercially available photopolymerization initiation aid (G) may be, for example, a commercial name of rEAB-F (manufactured by Hodogaya Chemical Co., Ltd.). In the colored photosensitive resin composition of the present invention, as a combination of a photopolymerization initiator. 0 and a photopolymerization initiator (G), for example, diethyl acetophenone / 4 may be mentioned. 4'-bis(diethylamino)benzophenone, 2-methyl-2-(2)-(4-methylthiophenyl)propanone-ι__/4, 4' - bis(diethylamino) benzophenone, 2-hydroxy-2-mercapto-1-phenylpropane one! Monoketone/4,4,bis(diethylamino)benzophenone, benzyldimethylketal/4,4,'-bis(diethylamino)benzophenone, 2 -hydroxy-2-methyl-i-[4-(2-hydroxyethyl 320834 24 200937116 oxy)phenyl]propane- ketone/4,4'-bis(diethylamino)benzophenone, 1-hydroxycyclohexyl phenyl ketone / 4, 4,-bis(diethylamino)benzophenone, 2 _ yl-2-yl yl yl yl) phenyl] propyl hydride + _ Oligomer/4,4'-bis(diethylamino)benzophenone, 2-benzyl-2-dimethylamino 1 (4-(N-)-based) ) butyl ketone ketone bis(diethylamino) dimercapto ketone, etc., and 2-mercapto-2-(N-morpholinylmethylthiophenyl)-propane- 1 -one / 4 4,-bis(diethylamino)dibenzophenone is preferred.至至1. 01至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至δ Mo ears. In the present invention, the coloring resin composition of the moon color contains a crosslinking accelerator (preferably, when the crosslinking agent is contained, the chemical resistance of the obtained coating film tends to be good.) ❹ Crosslinking as described above Examples of the enhancer (8) include a ring compound, a melamine derivative, and the like, and an epoxy compound is preferred. ', c As the above-mentioned Wei compound, it can be solved as: (4) A type resin, hydrogenation double test A type ring Oxygen resin, double powder double-preferred F-type epoxy resin North =, system = epoxy resin; alicyclic _ glyceride type resin, shrinking water, a latex resin, shrinking oxygen tree, the purpose of cutting, the production of nine cooked, etc. Resin; the above-mentioned humiliation 320834 25 200937116, (mercapto) propylene glycol vinegar (co) glycerin (co) methacrylate, isocyanuric acid triglyceride, and bisphenol A epoxy resin, aromatic An epoxy resin, an alicyclic epoxy resin, or a heterocyclic epoxy resin is preferred. In the colored photosensitive resin composition of the present invention, the content of the crosslinking enhancer (E) is relative to the binder resin (B) and 100 parts by mass of the total amount of the photopolymerizable compound (C) is usually 2 parts by mass or more. It is preferably 4 parts by mass or more, more preferably 10 parts by mass or more, particularly preferably 20 parts by mass or more, and usually 40 parts by mass or less, and preferably 35 parts by mass or less. The colored photosensitive resin of the present invention. The composition contains a solvent (F). Examples of the solvent (F) include ethers, aromatic hydrocarbons, ketones, alcohols, esters, guanamines, methylpyrrolidone, and dimercaptosulfoxide. Examples of the ethers include tetrahydroanthracene, tetrahydroσ-pyran, 1,4-dioxane, ethylene glycol monodecyl ether, ethylene glycol monoethyl ether, and ethylene glycol single. Propyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol didecyl ether, diethyl Glycol diethyl ether, diethylene glycol dipropyl light, diethylene glycol dibutyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate Ester, methyl cel losolve acetate, ethyl cellosolve acetate, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol Ethyl ether acetate, methoxybutyl acetate, r methoxy pentyl acetate, anisole, phenetole, decyl phenyl hydrazine, etc. as the aforementioned aromatic Examples of the hydrocarbons include benzene, toluene, diphenylbenzene, mesitylene, etc. 26 320834 200937116 9 . Examples of the above-mentioned class include acetone, 2-butanone, and 2-heptanone. , 3 g of hydrazine, 4 heptanone, 4-methyl-2-pentanone, cyclopentate, cyclohexyl, etc. * As the aforementioned alcohols, for example, decyl alcohol, ethanol, propanol, butanol, Examples of the ester include, for example, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, and butyl acrylate. Ester, isopropyl butyrate, ethyl butyrate, butyl butyrate, alkyl esters, methyl lactate, bismuth lactate, methyl mercaptoacetate, ethyl acetate, butyl vinegar Methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, ethoxyethyl acetate, ethoxyacetic acid ethyl acetate, 3-hydroxypropionic acid methyl vinegar, 3-jing Propionic acid Vinegar, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-hydroxypropionate, 2_ethyl hydroxypropionate, propyl 2-hydroxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, 2-ethoxyl Methyl vinegar propionate, 2-ethoxypropionic acid ethyl ketone, 2-carbyl-2-methylpropionic acid methyl vinegar, 2-hydroxy-2-methoxypropionic acid ethyl ester, 2-methoxy- Methyl 2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, methy 1 pyruvate, propyl ketone acetate, propyl pyruvate, acetamidine acetate Methyl ester, ethyl acetate ethyl acetate, methyl 2-ketobutyrate, ethyl 2-ketobutyrate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl Acetate, vinegar, etc. Examples of the above-mentioned amines include N,N-dimethyl decylamine and N,N-dimethylacetamide. Among these, propylene glycol monomethyl ether acetate or ethyl 3-ethoxypropionate is preferred, and it is more preferred to use them in combination. 320834 27 200937116 Further, the above solvents may be used singly or in combination of two or more types. The content of the solvent (F) in the coloring photosensitive resin composition is preferably from 70 to 95% by mass, more preferably from 75 to 90% by mass, based on the mass fraction of the photosensitive resin composition. When the content of the solvent (F) is within the above range, the flatness at the time of coating becomes good, and when the color filter is formed, the density is not insufficient, so that the display property tends to be good, which is preferable. The colored photosensitive resin composition of the present invention may further contain a surfactant (H). Examples of the surfactant (H) include a surfactant selected from the group consisting of a Si 1 i cone surfactant, a fluorine-based surfactant, and a polyoxo-based interface having a fluorine atom. At least one of the groups of the agents. The above-mentioned polyoxo-based surfactant may, for example, be a surfactant having a oxy-oxygen bond. Specifically, for example, Toray

Si 1 icone DC3PA, Toray Si 1 icone SH7PA, Toray Si 1 icone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Si 1 icone SH29PA, Toray Si 1 icone SH30PA, q Polyether modified oyster sauce SH8400C trade name: Toray Silicone System, KP321, KP322, KP323, KP324, KP326, KP340, KP34K, Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, TSF4460 (GE Toshiba Polyoxo Co., Ltd.) Wait. The fluorine-based surfactant may, for example, be an surfactant having a fluorocarbon chain. Specifically, for example, Fluorad (trade name) FC430, Fluorad FC431C Sumitomo 3M Company, Megaface (trade name) 28 320834 200937116 i F142D, Megaface F171, Megaface F172, Megaface F173, Megaface F177, Megaface FI83, Megaface R30 (Daily Oil* manufactured by Mok Chemical Industry Co., Ltd.), FTOP (trade name) EF3 (H, FTOP EF303, FTOP EF 351, FTOP EF352 (manufactured by New Akita Chemical Co., Ltd.), Surf Ion (trade name) S38, and Surf Ion S382. Surflon SC1 (H, Surf Ion SC105 (made by Asahi Glass Co., Ltd.), E5844 (made by Daikin Seika Co., Ltd.), BM-1000, BM-1100 (all are trade names: BM Chemie), etc. The surfactant having a gas atom, such as a surfactant having a siloxane chain and a fluorocarbon chain, may be exemplified by Megaface (registered trademark) R08, Megaface BL20, and the like. Megaface F475, Megaface F477, Megaface F443 (manufactured by Dainippon Ink Chemical Industry Co., Ltd.), etc. These surfactants may be used singly or in combination of two or more types. The content of surfactant (H) 'relative' The composition of the coloring photosensitive resin is preferably 0.0005 to 0.6% by mass, more preferably 0. 001 to 0.5% by mass, based on the mass fraction. The content of the surfactant (H) is as described above. When the coloring photosensitive resin composition is applied in the range, the flatness of the obtained coating film tends to be good, and it is preferable to form the pattern of the color filter using the colored photosensitive resin composition of the present invention. For example, the coloring photosensitive resin composition of the present invention is applied onto a substrate or another resin layer (for example, another photosensitive resin composition layer formed on the substrate), and the solvent is removed. a photolithography method in which a volatile layer is formed to form a colored layer, and the colored layer is exposed through a photomask, and after being imaged, hardened by at least one of heating or exposure by 320834 29 200937116; or A method in which a coloring photosensitive resin' composition is applied onto a substrate or another resin layer by an inkjet device to remove a volatile component such as a solvent to form a colored layer, and then heated or exposed at least one of them. Hardening Ink jet method, etc. - Examples of the coating device include a spin coater, a slit coater, a curtain coater, a cast coater, an inkjet device, and the like. . In order to remove a volatile component such as a solvent, for example, it can be heated by heating at a point above the point of use of the solvent, or can be reduced by depressurization and heated at a temperature below the point of removal to remove it. In the reticle, a light-shielding portion and a non-light-shielding portion are formed in accordance with the shape of the desired pattern. ° Exposure is performed using a light source such as a g-line, an h-line, or an i-line, using a device such as a stepper (StepPer/) or a mask alignment machine (Mask Aligner). The exposed color layer is subjected to development processing to form a pattern. The image forming process S is carried out using a developing device, usually by dipping in an experimental solution or by spraying an organic solution on the colored layer. After the image is developed, the rinsing process is often carried out to remove the test solution in the colored layer. After the rinsing treatment, a drying means such as a dryer is usually used to dry the colored layer after drying of the colored layer, and it is hardened by heating or exposure to a pattern. The resulting pattern is such that a red layer of color filters can be formed. For example, a green layer, a blue layer can be additionally formed and combined as a color filter 320834 30 200937116 * sheet. Further, the formation of the red layer may be different from the layer of other colors in the order in which they are formed. The resulting color filter can be used, for example, as a color filter for an image sensor or display device. According to the present invention, a color filter having a high contrast can be formed. (Embodiment) Hereinafter, the present invention will be described in more detail based on examples, but the present invention is not limited to these examples. Synthesis Example 1 <Synthesis of a binder resin (B1)> 333 g of propylene glycol monodecyl ether acetate was introduced into a 1 L flask equipped with a stirrer, a thermometer, a reflux cooling tube, a dropping funnel, and a glass introduction tube. Thereafter, nitrogen gas was introduced into the flask through a glass introduction tube, and the ambient gas in the flask was replaced with nitrogen. After that, the solution in the flask was heated to 100 φ ° C, and the N-benzoquinone maleimide was used in an amount of 2,7 g (0.10 mol), phenyl decyl acrylate. 7 g (0.40 摩尔), methacrylic acid 51.7 g (0.6 m), methyl methacrylate 90. 0 g (0. 9 m), azobisisobutyronitrile 5. 2 g A mixture of 182 g of propylene glycol monodecyl ether acetate was added dropwise, and after completion of the reaction, stirring was continued for 5 hours at 1 °C. After the stirring was terminated, the air was introduced into the flask through a glass introduction tube, and the ambient gas in the flask was replaced with air, and then glycidyl methacrylate was 28. 5 g [0.2 mol (relative to the thiol acrylic acid used in the reaction). , with 31 320834 200937116 mole fraction, 33 mole %)], ginseng (didecylamino fluorenyl) phenol 1. 3 g and argon argon 0.1 g into the flask, continued at 110 ° C After reacting for 6 hours, a resin B1 having a solid content of 31.3% and an acid value of 80 mg KOH/g was obtained. Here, the acid value refers to a measured value of the amount (mg) of potassium hydroxide required to neutralize 1 g of a polymer having an acid group such as a carboxylic acid, and is usually titrated by using an aqueous potassium hydroxide solution having a known concentration. Seek. The polystyrene-equivalent weight average molecular weight of the obtained binder resin (B1) as measured by the GPC method of the following conditions was 16,000.

Device: HLC-8120 GPC (manufactured by Tosoh Corporation) Column: TSK-GEL G2000 HXL Column temperature: 40 ° C Solvent: THF Flow rate: 1. 0 mL / min The solid concentration of the test liquid: 0. 001 to 0 . 01% by mass

Injection amount: 5 0 // L Detector: Standard material for RI calibration: TSK Standard polystyrene F-40, F-4, Fl, A-2500, A-500 (manufactured by Tosoh Corporation) Synthesis Example 2 <Adhesive Synthesis of Resin (B2)> 333 g of propylene glycol monothiol acetate was introduced into a 1 L flask equipped with a stirrer, a thermometer, a reflux cooling tube, a dropping funnel, and a glass introduction tube. Thereafter, nitrogen gas was introduced into the flask through a glass introduction tube, and the ambient gas in the flask was replaced with nitrogen. After that, the solution in the flask was heated to 1 〇〇32 320834 200937116 ° C, and then a dicyclopentanyl methacrylate (FA-513M; manufactured by 曰立化成公司) was used in a dropping funnel for 2 hours. g (0. 10 mol), methyl benzoate benzoate 88.0 g (0.50 mol), methacrylic acid 34.5 g (0.40 mol), azobisisobutyronitrile 3.3 g and A mixture of 164 g of propylene glycol monodecyl ether acetate was added dropwise, and after the completion of the dropwise addition, the mixture was further stirred at 100 ° C for 5 hours. After the stirring was terminated, air was introduced into the flask through a glass introduction tube, and the ambient gas in the flask was replaced with air, and then glycidyl methacrylate ester 21.5 g [0.15 mol (relative to the methacrylic acid used in the reaction) , in a molar fraction, 27 mole %)], ginseng (didecylaminomethyl) phenol 0. 9 g and hydroquinone 0. 145 g into the flask, continuous reaction at 110 ° C for 6 hours , the solid content is 28.7%, and the acid value is 8〇11^1 (011/boiled resin ugly 2. The obtained binder resin (B 2 ) is converted into polystyrene by the GPC method of the same conditions as above. The weight average molecular weight was 25,000. Synthesis Example 3 ❹ <Synthesis of a binder resin (B3)> In a 1 L flask equipped with a stirrer, a thermometer, a reflux cooling tube, a dropping funnel, and a glass introduction tube, propylene glycol monomethyl group was introduced. 333 g of ethyl ether acetate. Then, nitrogen gas was introduced into the flask through a glass introduction tube, and the atmosphere in the flask was replaced with nitrogen gas. Thereafter, the solution in the flask was heated to 100 ° C, and then a dropping funnel was used. Within the hour will be dicyclopentyl methacrylate (FA-513 Μ ; 2 g (0. 10 m), benzyl methacrylate 79.5 g (0.45 m), methacrylic acid 38.5 g (0.45 m), azo double Isobutyronitrile 3.3 g and propylene glycol monomethyl ether acetate 164 33 320834 200937116 g The mixture was dropped, and after the completion of the dropwise addition, the mixture was further stirred at 100 ° C for 5 hours. After the stirring was terminated, the glass was introduced through the tube. After introducing air into the flask and replacing the ambient gas in the flask with air, 21.5 g of glycidyl methacrylate [0.15 mol (relative to the mercaptoacrylic acid used in the reaction, in terms of molar fraction) 30 mol%)], ginseng (didecylaminomethyl) phenol 0.9 g and 氲醌0. 145 g were charged into the flask, and the reaction was continued at 110 ° C for 6 hours to obtain a solid fraction of 28.6% and an acid value of 105 mg KOH / g resin B3.

The polystyrene-equivalent weight average molecular weight of the obtained binder resin (B3) measured by the GPC method under the same conditions as above was 30,000. The components used in the present embodiment are as follows, and hereinafter, the description is omitted. (A-1) Colorant · Compound represented by formula (3) (Orasol Red 3GL; manufactured by Ciba Specialty Chemicals Co., Ltd.)

(A-2) Colorant: a compound represented by the formula (4) (Orasol Red G; manufactured by Ciba Specialty Chemicals Co., Ltd.) 34 320834 200937116

(A-3) Colorant: Compound represented by formula (5) (Valifast Red 3312; manufactured by Orient Chemical Industry Co., Ltd.)

G (A-4) colorant: a compound represented by the formula (6) (Valifast Red 3320; manufactured by Orient Chemical Industries, Ltd.) 35 320834 200937116

θ (A-5) colorant: a compound represented by the formula (7) (Val i fast Red ❹ 1308; manufactured by Orient Chemical Industry Co., Ltd.)

HO

HOOC (A-6) colorant: a compound represented by the formula (8) (Valifast Red 1360; manufactured by Orient Chemical Industry Co., Ltd.)

(B-1) Resin B1 obtained in Synthesis Example 1 (B-2) Resin B2 obtained in Synthesis Example 2 (B-3) Resin B3 obtained in Synthesis Example 3 36 320834 200937116 Λ (C-1) Photopolymerizable Compound: Dipentaerythritol hexaacrylate (Nippon Chemical Co., Ltd.) (C-2) Photopolymerizable compound: Trimethylolpentane tripropionate (manufactured by Nippon Kayaku Co., Ltd.) * (D-1) Photopolymerization Starting agent: 2-mercapto-2-(N-morpholinyl)-1-(4-methylthiophenyl)propan-1-one (D-2) photopolymerization initiator: 2, 4- Bis(trichloromethyl)-6-mallowyl-1,3,5-trin (D-3) photopolymerization initiator: 0χΕ-〇1 (lanthanide compound; Ciba Specialty Chemicals Co., Ltd.) G-1) Photopolymerization start-up aid: 4, 4'-bis(diethylamino)benzophenone (G-2) photopolymerization starter: 2, 4-diethylthioketidine (E-1) Epoxy compound: 邠 shot is like ^ 跎 (3) - 丨 乩 乩 - 别 ^ Sumitomo Chemical Co., Ltd.) (F-1) > gluten. propylene glycol monothiol linkage acetate (hereinafter, slightly PM(F) solvent: propylene glycol monodecyl ether (hereinafter, abbreviated as pGME) (F-3) solvent: ethyl lactate (F-4) solvent: 3-ethoxypropionic acid Ester (H-1) leveling agent: Megaface F475 (product name, manufactured by Dainippon Ink Chemicals Co., Ltd.) Example 1 [Preparation of coloring photosensitive resin composition 1] The following compound 'mixed' can be used to obtain a coloring resin composition (A~l) 9·500 Parts by mass 320834 37 200937116 (Bl) (Cl) (Dl) (D-2) (Gl) (Fl) (F-2) (Hl) 3 · 189 parts by mass 4. 784 parts by mass 0.718 parts by mass 〇 558 mass 239 parts by mass of 27. 540 mass 伶 53. 460 parts by mass of 0.012 parts by mass on the glass substrate [#Π37; manufactured by Corning Co., Ltd.], the obtained colored photosensitive resin composition 1 was coated by spin coating At 1Q (re dry for 3 minutes, the volatile component is volatilized to form a colored photosensitive resin composition layer. After cooling, the colored photosensitive resin composition layer is irradiated with an I-line [wavelength 365 nm] via a photomask. The light source of the I-line is an ultrahigh-pressure mercury lamp, and the amount of light is 150 mJ/cm2. After the exposure, heat treatment is performed at 220 ° C for 20 minutes to obtain a glass substrate on which a coating film is formed. The color of the coating film on the obtained glass substrate was measured using a color measuring machine (0SP-SP-200; OLYMPU) The measurement was carried out, and Rx and contrast as color characteristics were measured using a contrast meter (color-color difference meter BM-5A; manufactured by Topcon Corporation). The results are shown in Tables 1 and 2. The coating film on the obtained glass substrate was immersed in PGMEA maintained at 23 ° C for a large excess with respect to the coating film, and left for 30 minutes, and then the color was measured using a color measuring machine to obtain a pre-impregnation. The color difference of chromaticity. In addition, in addition to 38 320834 200937116, the impregnation liquid was changed to PGME 祌 ♦ from the 4 μ tube generation, the same operation as described above was performed to obtain the color difference. These results are shown in Table 1 as pgmea tolerance and brain tolerance. When the color difference is 5 or less, the solvent resistance of the coating film is good, and at 5 o'clock, the coating film has no problem in terms of money, and when it exceeds 10, the solvent resistance of the coating film is poor. Example 2 [Preparation of coloring photosensitive resin composition 2] 着色 mixing the following compound 'a coloring sensitizing resin composition 2, (A-2) (B-1) (C-1) (D-1) (D-2) (G-1) (F-1) (F-2) (H-1) 9. 500 parts by mass 3. 189 parts by mass 4. 784 parts by mass 0.718 parts by mass 0.558 parts by mass 0. 23 Θ mass ❹ 27. 540 parts by mass 53. 460 parts by mass of 0. 012 parts of the rest and the actual 1 (four) operation surface evaluation, the results are shown in the table. Example 3 [Preparation of coloring photosensitive resin composition 3] The following compound ' was mixed to obtain a coloring photosensitive resin composition (A-1). 9.500 parts by mass 320834 39 200937116 (Bl) (Cl) (El) ( Dl) (D-2) (Gl) (Fl) (F-3) (Hl) 2. 547 parts by mass 3. 821 parts by mass 1. 910 parts by mass 0. 573 parts by mass 0. 446 parts by mass of 0. 191 mass 40 parts, 500 parts by mass, 40.500 parts by mass, 0. 012 parts by mass, the same operation as in Example 1 and evaluation, and the results are shown in Table 1. Example 4 [Modulation of coloring photosensitive resin composition 4] The colored photosensitive resin composition 4 was obtained by the following compound '. (A-2) 9. 500 parts by mass (B-1) 2.547 parts by mass (C-1) 3.821 parts by mass (E-1) 1.910 parts by mass (D-1) 0.573 parts by mass (D-2) 0.446 parts by mass (G-1) 0.191 parts by mass (F-1) 40.500 parts by mass (F-3) 40.500 parts by mass (H-1) 0.012 parts by mass 40 320834 200937116 The rest of the same operation as in Example 1 was carried out, and the results were expressed in in FIG. 1. Example 5 [Preparation of colored photosensitive resin composition 5] The following compound was mixed to obtain a colored photosensitive resin composition 5. (A-3) 9. 500 parts by mass (B-1) 3. 189 parts by mass (C-1) 4. 784 parts by mass (D-1) 0.718 parts by mass (D-2) 0. 558 parts by mass (G) -1) 0.239 parts by mass (F-1) 27. 540 parts by mass (F-2) 53. 460 parts by mass (H-1) 0. 012 parts by mass Only the contrast was evaluated in the same manner as in Example 1. The results are shown in Table 2. Example Θ [Preparation of Colored Photosensitive Resin Composition 6] The following compound was mixed to obtain a colored photosensitive resin composition 6. (A-4) 9. 500 parts by mass (B-1) 3. 189 parts by mass (C-1) 4. 784 parts by mass (D-1) 0. 718 parts by mass (D-2) 0.558 parts by mass 41 320834 200937116 (G-1) 0. 239 parts by mass (F-1) 27. 540 parts by mass (F-2) 53. 460 parts by mass (H-1) 0. 012 parts by mass only the contrast is the same as in the first embodiment The evaluation was performed by operation, and the results are shown in Table 2. Example 7 [Preparation of Colored Photosensitive Resin Composition 7] The following compound was mixed to obtain a colored photosensitive resin composition 7. (A-3) 9. 500 parts by mass (B-1) 3. 189 parts by mass (C-1) 4. 784 parts by mass (E-1) 1. 910 parts by mass (D-1) 0. 718 parts by mass (D-2) 0. 558 parts by mass (G-1) 0. 239 parts by mass (F-1) 27. 540 parts by mass (F-2) 53. 460 parts by mass (H-1) 0.012 parts by mass only contrast The evaluation was carried out in the same manner as in Example 1, and the results are shown in Table 2. Example 8 [Preparation of colored photosensitive resin composition 8] The following compound was mixed to obtain a colored photosensitive resin composition 8. 42 320834 200937116 (A-4) 9. 500 parts by mass (B-1) 3. 189 parts by mass (C-1) 4. 784 parts by mass (E-1) 1. 910 parts by mass (D-1) 0. 718 parts by mass (D-2) 0.558 parts by mass (G-1) 0. 239 parts by mass (F-1) 27. 540 parts by mass (F-2) 53. 460 parts by mass (H-1) 0. 012 by mass Only the contrast was evaluated in the same manner as in Example 1, and the results are shown in Table 2. Comparative Example 1 [Preparation of Comparative Colored Photosensitive Resin Composition 1] A comparatively colored photosensitive resin composition 1 was obtained by mixing the following compounds. (A-5) 9.500 parts by mass (B-1) 2.547 parts by mass (C-1) 3.821 parts by mass (E-1) 1.910 parts by mass (D-1) 0.573 parts by mass (D-2) 0. 446 parts by mass (G-1) 0. 191 parts by mass (F-1) 40. 500 parts by mass (F-2) 40.500 parts by mass 43 320834 200937116 (Hl) _ Q· The mass of the sample is evaluated and the result is only contrast It is shown in Table 2 with the examples. Comparative Example 2 [Comparison of Comparison of Colored Photosensitive Resin Composition 2] The following compounds were mixed to obtain Comparative 2. Composition of photosensitive resin 9.5 parts by mass 2. 547 parts by mass 3. 821 parts by mass 1. 910 parts by mass 0· 573 parts by mass 0· 446 parts by mass 0· 191 parts by mass 40. 500 parts by mass 40 5〇〇质量份0. 012 parts by mass (A-6) (B-1) (C-1) (E-1) (D-1) (D-2) (G-1) (F-1 (F-3) (H-1) The results of the same operation as in Example 1 are shown in Table 2 only for the contrast of the beta shell. The term 320834 200937116 [Table 1]

Rx Contrast PGMEA Resistant PGME Financial Example 1 0. 658 7044 44. 1 46. 7 Example 2 0. 658 7284 81. 4 93. 5 Example 3 0. 658 6037 0. 3 0. 2 Example 4 0 658 6565 0. 2 2. 7 [Table 2] Rx Contrast Example 5 0. 658 5903 Example 6 0. 658 5974 Example 7 0. 658 4234 Example 8 0. 658 3963 Comparative Example 1 0. 658 1926 Comparative Example 2 0.472 2980 In Examples 1 to 8 and Comparative Examples 1 to 2, the measurement results of the contrast at the same value of ❹ X of CIE 1931 were compared. In Comparative Example 2, since it was impossible to produce a film of the same X value, it was represented by the X value and the comparative value at the same film thickness (2.0/zm). As is apparent from Tables 1 and 2, in the coloring agents used in Examples 1 to 8, the contrast was good, and when these coloring agents were used, a color filter excellent in color forming properties was obtained. As is clear from Table 1, in the color filters formed by using the colored photosensitive resin composition containing a coloring agent and a crosslinking enhancer in Examples 3 and 4, the contrast, PGMEA resistance, and PGME resistance were good. Repeat coating 45 320834 200937116, the colored photosensitive resin composition of the present invention, is shown for use in the production of color filters. [Simple description of the diagram] None. [Main component symbol description] No 0 ❿ ❹ 46 320834

Claims (1)

200937116 · * VII. Patent application scope: 1. A coloring photosensitive resin composition containing: coloring agent (A), adhesive, binder resin (B), photopolymerizable compound (C), photopolymerization a starting agent (D) and a solvent (F); wherein the coloring agent (A) is a coloring agent containing a compound represented by the formula (A-!), Θ 〇 [In the formula (A-Ι), R1 to γ are each independently, and represent a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, a linear or branched alkyl group having 1 to 5 carbon atoms, a nitro group, and a benzene group. a group, -S〇2NHR21 or -C00R21; 〇R21 represents a hydrogen atom, an aliphatic hydrocarbon group having 1 to 8 carbon atoms, a cyclohexyl group, an alkyl group having a carbon number of from 4 to 4, and a carbon number of 2 to 15 alkoxyalkyl, -R3i_c〇_〇_r32, -R31_〇_c〇_r32, or an aralkyl group having 7 to 10 carbon atoms; R represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms , π represents a monovalent aliphatic hydrocarbon group having 1 to 8 carbon atoms; R and R each independently represent a hydrogen atom, a fluorenyl group, and a ethaneamine group; the earth soil 驭Μ represents Cr or Co; 320834 47 200937116 t D a hydrogen atom, a monovalent metal cation or a monovalent cation of a compound having a xanthene backbone]. 2. The colored photosensitive resin composition of claim 1, wherein the binder resin (8) is a resin having a polymerizable unsaturated bond in a side chain. 0. Coloring sensitivity according to claim 1 or 2 A resin composition further comprising a crosslinking enhancer (E). 4. The color-sensitive resin composition according to item 3 of the patent application, wherein the 'crosslinking enhancer (E) is a compound containing an epoxy group. A color light-passing sheet comprising a pattern formed by the color-sensitive photosensitive resin composition of any of the applications of the U 4th item of the patent application. The coloring photosensitive tree of any one of claims 1 to 4 of the patent application is applied to the manufacture of a color filter. The use of the compound of the formula (A-Ι) for the production of a colored photosensitive resin composition: Θ D, [In the formula (A-Ι), RI to R18 +惫® κ are independent of each other, representing a hydrogen atom, a fluorine atom, an atom of Australia, a linear or branched base of carbon numbers 1 to 5, 320834 48 I 200937116 Nitro, phenyl, -S〇2NHR21 or -C00R21 ; R21 represents a hydrogen atom, an aliphatic hydrocarbon group having 1 to 8 carbon atoms, a cyclohexyl group, and an alkylcyclohexyl group having a carbon number of 1 to 4 in the alkyl group. An alkoxyalkyl group having 2 to 15 carbon atoms, _R31_C〇_〇_R32, _r31_〇_c〇_r32, or an aralkyl group having 7 to 1 carbon atoms; R31 represents a carbon number of 1 to 8 a valent aliphatic hydrocarbon group, R32 represents a monovalent aliphatic hydrocarbon group having 1 to 8 carbon atoms; 〇R19 and R2. They are each independently represented by a halogen atom, a methyl group, an ethyl group or an amine group; Μ represents Cr or Co; represents a chlorine atom, a monovalent metal cation or a monovalent cation of a compound having a blunt bone. ❹ 320834 49 200937116 IV. Designated representative map: There is no schema in this case. * (1) The representative representative of the case is: ( ). (2) A brief description of the symbol of the representative figure: ❹ 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: Factory -1H R19 R4 R3 U 5 320834