WO2014196660A1 - Composition de résine durcissable colorée - Google Patents

Composition de résine durcissable colorée Download PDF

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Publication number
WO2014196660A1
WO2014196660A1 PCT/JP2014/065522 JP2014065522W WO2014196660A1 WO 2014196660 A1 WO2014196660 A1 WO 2014196660A1 JP 2014065522 W JP2014065522 W JP 2014065522W WO 2014196660 A1 WO2014196660 A1 WO 2014196660A1
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Prior art keywords
group
formula
carbon atoms
pigment
compound
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PCT/JP2014/065522
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English (en)
Japanese (ja)
Inventor
鈴木　智也
龍虎 呉
哲郎 赤坂
芦田　徹
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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Priority to JP2015521518A priority Critical patent/JP6493880B2/ja
Priority to CN201480032399.XA priority patent/CN105263968B/zh
Priority to KR1020157035561A priority patent/KR102224883B1/ko
Publication of WO2014196660A1 publication Critical patent/WO2014196660A1/fr
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/24—Disazo or polyazo compounds
    • C09B45/26—Disazo or polyazo compounds containing chromium
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/24—Disazo or polyazo compounds
    • C09B45/30—Disazo or polyazo compounds containing cobalt
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C09B69/103—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing a diaryl- or triarylmethane dye
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C09B69/106—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an azo dye
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments

Definitions

  • the present invention relates to a colored curable resin composition.
  • Colored curable resin compositions are used for the production of color filters used in display devices such as liquid crystal display panels, electroluminescence panels, and plasma display panels.
  • this colored curable resin composition it is known to use a pigment or a dye as a colorant (Non-Patent Document 1).
  • An object of the present invention is to provide a colored curable resin composition capable of obtaining a color filter having better brightness and contrast.
  • the colored curable resin composition which is a coloring agent containing the compound and the compound represented by Formula (A2).
  • R 1 to R 18 each independently represents a hydrogen atom, a halogen atom, a monovalent aliphatic hydrocarbon group having 1 to 10 carbon atoms, a nitro group, or —SO 2 R 29 .
  • R 29 represents —OH, —NHR 30 or —R 32 .
  • R 30 represents a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 10 carbon atoms, a cyclohexyl group optionally substituted with an alkyl group having 1 to 4 carbon atoms, -R 31 -O-R 32 ,- R 31 —CO—O—R 32 , —R 31 —O—CO—R 32 , or an aralkyl group having 7 to 10 carbon atoms is represented.
  • R 31 represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms.
  • R 32 represents a monovalent aliphatic hydrocarbon group having 1 to 8 carbon atoms.
  • R 19 and R 20 each independently represents a hydrogen atom, a methyl group, an ethyl group or an amino group.
  • M 1 represents Cr or Co.
  • Y represents Na or K.
  • R 21 to R 24 each independently represents a hydrogen atom, —R 26, or an aromatic hydrocarbon group having 6 to 10 carbon atoms.
  • the hydrogen atom contained in the aromatic hydrocarbon group having 6 to 10 carbon atoms is a halogen atom, —R 26 , —OH, —OR 26 , —SO 3 — , —SO 3 Na, —CO 2 H, —CO 2 R 26, SO 3 H, optionally substituted by -SO 3 R 26 or -SO 2 NHR 28.
  • R 25 represents —SO 3 — , —SO 3 Na, —CO 2 H, —CO 2 R 26 , —SO 3 H or SO 2 NHR 28 .
  • R 2a represents an alkyl group having 1 to 3 carbon atoms.
  • R 28 represents a hydrogen atom, —R 26 , —CO 2 R 26 or an aromatic hydrocarbon group having 6 to 10 carbon atoms, and the hydrogen atom contained in the aromatic hydrocarbon group having 6 to 10 carbon atoms is it may be substituted by -R 26 or -OR 26.
  • m represents an integer of 0 to 5. When m is an integer of 2 or more, the plurality of R 25 may be the same or different.
  • X represents a halogen atom.
  • a represents an integer of 0 or 1.
  • [2] The colored curable resin composition according to [1], wherein the colorant (A) is a colorant further comprising at least one pigment selected from the group consisting of a yellow pigment, an orange pigment, and a red pigment.
  • R 55 represents —SO 3 — or —SO 2 NHR 28 .
  • R 26 , R 28 , X and a represent the same meaning as described above.
  • the pigment is C.I. I. Pigment yellow 138, C.I. I. Pigment yellow 139, C.I. I. Pigment yellow 150, C.I. I. Pigment red 177, C.I. I. Pigment red 242 and C.I. I.
  • the colored curable resin composition of the present invention According to the colored curable resin composition of the present invention, a color filter excellent in brightness and contrast can be obtained.
  • the colored curable resin composition of the present invention includes a colorant (A), a resin (B), a photopolymerizable compound (C), a photopolymerization initiator (D), and a solvent (E), and the colorant (A).
  • a colorant (A) Is a compound represented by the following formula (A1) (hereinafter sometimes referred to as “compound (A1)”) and a compound represented by the following formula (A2) (hereinafter sometimes referred to as “compound (A2)”).
  • [In formula (A1), R 1 ⁇ R 18 Each independently represents a hydrogen atom, a halogen atom, a monovalent aliphatic hydrocarbon group having 1 to 10 carbon atoms, a nitro group, or -SO. 2 R 29 Represents.
  • R 29 Are —OH, —NHR 30 Or -R 32 Represents.
  • R 30 Is a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 10 carbon atoms, a cyclohexyl group optionally substituted with an alkyl group having 1 to 4 carbon atoms, -R 31 -O-R 32 , -R 31 -CO-O-R 32 , -R 31 -O-CO-R 32 Or an aralkyl group having 7 to 10 carbon atoms.
  • R 31 represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms.
  • R 32 Represents a monovalent aliphatic hydrocarbon group having 1 to 8 carbon atoms.
  • R 19 And R 20 Each independently represents a hydrogen atom, a methyl group, an ethyl group or an amino group.
  • M 1 Represents Cr or Co.
  • Y represents Na or K.
  • [In formula (A2), R 21 ⁇ R 24 Each independently represents a hydrogen atom, -R 26 Alternatively, it represents an aromatic hydrocarbon group having 6 to 10 carbon atoms.
  • the hydrogen atom contained in the aromatic hydrocarbon group having 6 to 10 carbon atoms is a halogen atom, -R 26 , -OH, -OR 26 , -SO 3 ⁇ , -SO 3 Na, -CO 2 H, -CO 2 R 26 , -SO 3 H, -SO 3 R 26 Or -SO 2 NHR 28 May be substituted.
  • R 25 Is -SO 3 ⁇ , -SO 3 Na, -CO 2 H, -CO 2 R 26 , -SO 3 H or SO 2 NHR 28 Represents.
  • R 26 Represents a saturated hydrocarbon group having 1 to 20 carbon atoms.
  • R b Represents an alkyl group having 1 to 3 carbon atoms.
  • R 28 Is a hydrogen atom, -R 26 , -CO 2 R 26 Or an aromatic hydrocarbon group having 6 to 10 carbon atoms, and the hydrogen atom contained in the aromatic hydrocarbon group having 6 to 10 carbon atoms is -R 26 Or -OR 26 May be substituted.
  • M represents an integer of 0 to 5.
  • m is an integer of 2 or more, a plurality of R 25 May be the same or different.
  • X represents a halogen atom.
  • a represents an integer of 0 or 1.
  • the monovalent aliphatic hydrocarbon group having 1 to 10 carbon atoms includes methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, n- Pentyl group, n-hexyl group, n-heptyl group, n-octyl group, decyl group, 1-methylbutyl group, 1,1,3,3-tetramethylbutyl group, 1,5-dimethylhexyl group, 1,6 -A dimethylheptyl group, 2-ethylhexyl group, 1,1,5,5-tetramethylhexyl group etc.
  • R in formula (A1) 30 examples of the alkyl group having 1 to 4 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, and tert-butyl group.
  • R in formula (A1) 31 As the divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms, methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl Group, butane-1,3-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group and the like. .
  • the cyclohexyl group which may be substituted with an alkyl group having 1 to 4 carbon atoms includes 2-methylcyclohexyl group, 2-ethylcyclohexyl group, 2-propylcyclohexyl group, 2-isopropylcyclohexyl group and 2-butylcyclohexyl.
  • R in formula (A1) 30 -R 31 -O-R 32
  • methoxymethyl group ethoxymethyl group, propoxymethyl group, methoxyethyl group, ethoxyethyl group, propoxyethyl group, methoxypropyl group, ethoxypropyl group, propoxypropyl group, 2-oxo-4-methoxybutyl group, octyl
  • An oxypropyl group, a 3-ethoxypropyl group, a 3- (2-ethylhexyloxy) propyl group, etc. are mentioned.
  • R in formula (A1) 30 -R 31 -CO-O-R 32 examples thereof include methoxycarbonylmethyl group, methoxycarbonylethyl group, ethoxycarbonylmethyl group, ethoxycarbonylethyl group, propoxycarbonylmethyl group, propoxycarbonylethyl group, butoxycarbonylmethyl group, butoxycarbonylethyl group and the like.
  • R in formula (A1) 30 -R 31 -O-CO-R 32
  • acetyloxymethyl group acetyloxyethyl group, ethylcarbonyloxymethyl group, ethylcarbonyloxyethyl group, propylcarbonyloxymethyl group, propylcarbonyloxyethyl group, butylcarbonyloxymethyl group, butylcarbonyloxyethyl group, etc.
  • acetyloxymethyl group acetyloxyethyl group, ethylcarbonyloxymethyl group, ethylcarbonyloxyethyl group, propylcarbonyloxymethyl group, propylcarbonyloxyethyl group, butylcarbonyloxymethyl group, butylcarbonyloxyethyl group, etc.
  • R in formula (A1) 1 ⁇ R 18 -SO 2 R 29
  • a sulfo group a sulfamoyl group; N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N- sec-butylsulfamoyl group, N-tert-butylsulfamoyl group, N-pentylsulfamoyl group, N- (1-ethylpropyl) sulfamoyl group, N- (1,1-dimethylpropyl) sulfamoyl group, N- (1,2-dimethylpropyl) sulfamoyl group, N- (2,2-dimethylpropyl)
  • -SO 2 R 32 As methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, isopropylsulfonyl group, n-butylsulfonyl group, sec-butylsulfonyl group, tert-butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, heptylsulfonyl group, octyl Sulfonyl group, 1-methylbutylsulfonyl group, 1,1,3,3-tetramethylbutylsulfonyl group, 1,5-dimethylhexylsulfonyl group, 1,6-dimethylheptylsulfonyl group, 2-ethylhexylsulfonyl group and 1, Examples include 1,5,5-tetramethylhexyls
  • the compound of the present invention is -SO 2 R 32 R 11 ⁇ R 14 At least one of R and R 15 ⁇ R 18 At least one of which is -SO 2 R 32 It is preferable that -SO 2 R 32 A plurality of R, a plurality of R 32 May be the same as or different from each other.
  • Preferred examples of the anion moiety of the compound (A1) include anions represented by formula (1-b1) to formula (1-b60).
  • Compound (A1) can be produced by reacting a compound represented by formula (1d) (hereinafter sometimes referred to as “compound (1d)”) with a chromium compound or a cobalt compound in an organic solvent. .
  • R 1 ⁇ R 5 , R 11 ⁇ R 14 And R 19 Represents the same meaning as described above.
  • the chromium compound include chromium formate, chromium acetate, chromium chloride, chromium fluoride and the like, preferably chromium formate and chromium acetate.
  • the cobalt compound include cobalt formate and cobalt acetate.
  • the organic solvent used in the reaction include dichloromethane, chloroform, tetrahydrofuran, toluene, acetonitrile and the like, and the amount used is not limited.
  • the reaction temperature is usually 70 to 100 ° C.
  • the amount of compound (1d) to be used is generally 2-4 mol with respect to 1 mol of the chromium compound or cobalt compound.
  • Preferred examples of compound (1d) include compounds represented by formula (1-a1) to formula (1-a64).
  • the compound (1d) includes a diazonium salt represented by the formula (1b) (hereinafter sometimes referred to as “diazonium salt (1b)”) and a pyrazole compound represented by the formula (1c) (hereinafter referred to as “pyrazole compound (1c)”).
  • the diazonium salt (1b) is obtained, for example, by diazotizing an amine represented by the formula (1a) (hereinafter sometimes referred to as “amine (1a)”) with nitrous acid, nitrite or nitrite. .
  • amine (1a) represented by the formula (1a)
  • R 11 ⁇ R 14 Represents the same meaning as described above.
  • a 1- Represents an inorganic or organic anion.
  • the inorganic anion include fluoride ion, chloride ion, bromide ion, iodide ion, perchlorate ion, hypochlorite ion, and the like.
  • Examples of the organic anion include CH.
  • the reaction of the diazonium salt (1b) and the pyrazole compound (1c) is usually carried out in an aqueous solvent, and examples of the aqueous solvent include N-methylpyrrolidone.
  • the reaction temperature is preferably -5 ° C to 60 ° C, more preferably 0 ° C to 30 ° C.
  • the reaction time is preferably 1 to 12 hours, more preferably 1 to 4 hours.
  • Compound (1d) is -SO 2 R 29 -SO 2 R 29 -SO 2 NHR 30 -SO 2 NHR 30
  • an azo compound having a sulfo group in the compound (1d) (hereinafter referred to as “compound (1s)”) is synthesized, and the sulfo group (—SO 2) is synthesized with a halogenated thionyl compound.
  • sulfonyl halide (-SO) 2 X;
  • X is a halogen atom) to obtain a sulfonyl halide compound, and then a sulfonyl halide compound and an amine (R 30 NH 2 ) To form a compound (1s) by sulfonamidation of the sulfo group.
  • the halogenated thionyl compound include thionyl fluoride, thionyl chloride, thionyl bromide, thionyl iodide and the like, preferably thionyl chloride and thionyl bromide, and particularly preferably thionyl chloride.
  • the amount of thionyl halide to be used is preferably 1 to 10 mol per 1 mol of compound (1s).
  • the sulfonyl halide is performed in a solvent.
  • the solvent include ethers such as 1,4-dioxane (particularly preferably cyclic ethers); chloroform, methylene chloride, carbon tetrachloride, 1,2-dichloroethane, dichloroethylene, trichloroethylene, perchloroethylene, dichloropropane, Halogenated hydrocarbons such as amyl chloride and 1,2-dibromoethane can be used.
  • the usage-amount of a solvent is 3 mass parts or more (preferably 5 mass parts or more) with respect to 1 mass part of compound (1s), and is 10 mass parts or less (preferably 8 mass parts or less).
  • N, N-dialkylformamide for example, N, N-dimethylformamide, N, N-diethylformamide, etc.
  • the amount used is, for example, 0.05 to 1 mol with respect to 1 mol of the thionyl halide compound.
  • reaction temperature in the sulfonyl halide formation is, for example, 0 ° C. or higher, preferably 30 ° C. or higher and 70 ° C. or lower, more preferably 30 ° C. or higher and 60 ° C. or lower.
  • the reaction time is, for example, 0.5 hours or more, preferably 3 hours or more and 8 hours or less, more preferably 3 hours or more and 5 hours or less.
  • the sulfonyl halide compound prepared as described above is isolated from the amine (R 30 NH 2 In the reaction mixture without isolation.
  • the reaction mixture and water may be mixed, and the precipitated crystals may be collected by filtration.
  • the crystals of the obtained sulfonyl halide compound are amine (R 30 NH 2 You may wash with water and dry as needed before reaction with).
  • Amine (R 30 NH 2 ) Include n-propylamine, n-butylamine, n-hexylamine, dimethylhexylamine (1,5-dimethylhexylamine, etc.), tetramethylbutylamine (1,1,3,3-tetramethylbutylamine, etc.), Examples include ethylhexylamine (such as 2-ethylhexylamine), aminophenylbutane (such as 3-amino-1-phenylbutane), and isopropoxypropylamine.
  • Amine (R 30 NH 2 ) Is used in an amount of 2 mol or more and 10 mol or less, preferably 2 mol or more and 7 mol or less with respect to 1 mol of the sulfonyl halide compound.
  • Sulfonyl halide compounds and amines (R 30 NH 2 ) The order of addition to sulfonyl halide compound is not particularly limited, but amine (R 30 NH 2 ) Is preferably added (dropped).
  • sulfonyl halide compounds and amines (R 30 NH 2 ) Is preferably carried out in a solvent.
  • the solvent the same solvent as that used for preparing the sulfonyl halide compound can be used.
  • basic catalysts include tertiary amines (aliphatic tertiary amines such as triethylamine and triethanolamine; aromatic tertiary amines such as pyridine), and secondary amines (aliphatic secondary amines such as diethylamine; piperidine, etc. And cycloaliphatic secondary amines).
  • tertiary amines particularly aliphatic tertiary amines such as triethylamine are preferable.
  • the amount of basic catalyst used is amine (R 30 NH 2 ) To 1.1 mol to 6 mol, preferably 1.1 mol to 5 mol.
  • Sulfonyl halide compound with amine (R 30 NH 2 ) And a basic catalyst are added, the timing of addition of the basic catalyst is not particularly limited, and amine (R 30 NH 2 ) Before or after the addition of amine (R 30 NH 2 ) May be added at the same timing. Further, it may be added after mixing with a reactive amine in advance. 30 NH 2 ) May be added separately.
  • Sulfonyl halide compounds and amines (R 30 NH 2 ) Is, for example, 0 ° C. or higher and 50 ° C.
  • the reaction time is 1 to 5 hours.
  • the method for obtaining the target compound (1d) from the reaction mixture is not particularly limited, and various known methods can be employed.
  • the reaction mixture is preferably mixed with an acid (for example, acetic acid and the like) and water, and the precipitated crystals are collected by filtration.
  • the acid is preferably prepared by preparing an aqueous solution of the acid in advance, and then adding the reaction mixture to the aqueous solution.
  • the temperature at which the reaction mixture is added is preferably 10 ° C. or higher and 50 ° C. or lower, more preferably 20 ° C. or higher and 50 ° C. or lower, and further preferably 20 ° C.
  • R of formula (A2) 26 Examples of the saturated hydrocarbon group having 1 to 20 carbon atoms in are methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, and n-octyl.
  • n-octyl group n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group
  • a linear alkyl group such as a group, n-octadecyl group, n-nonadecyl group, n-icosyl group; Isopropyl group, isobutyl group, sec-butyl group, isopentyl group, 1-methylpentyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylpentyl group, 1-ethylbutyl group, 2-ethylbutyl group, 1- Methylhexyl group, 2-methylhexyl group, 3-methylhe
  • R 2a Represents an alkyl group having 1 to 3 carbon atoms.
  • -CO of formula (A2) 2 R 26 examples thereof include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, a hexyloxycarbonyl group, and an icosyloxycarbonyl group.
  • -SO of formula (A2) 3 R 26 examples thereof include methanesulfonyl, ethanesulfonyl, hexanesulfonyl, decanesulfonyl and the like.
  • -SO of formula (A2) 2 NHR 28 As sulfamoyl, methanesulfamoyl, ethanesulfamoyl, propanesulfamoyl, isopropanesulfamoyl, butanesulfamoyl, isobutanesulfamoyl, pentansulfamoyl, isopentansulfamoyl, neopentansulfamoyl , Cyclopentanesulfamoyl, hexanesulfamoyl, cyclohexanesulfamoyl, heptanesulfamoyl, cycloheptanesulfamoyl, octanessulfamoyl, 2-ethylhexanesulfamoyl, 1,5-dimethylhexanesulfamoyl , Cyclooctanesulfamoyl, nonanesulfam
  • the compound represented by the formula (A2) is a compound represented by the formula (A2-1).
  • R 45 Is -SO 3 ⁇ Or -SO 2 NHR 28 Represents.
  • R 46 Is a hydrogen atom, -SO 3 ⁇ Or -SO 2 NHR 28 Represents.
  • R 26 , R 28 , X and a represent the same meaning as described above.
  • the compound represented by the formula (A2) is a compound represented by the formula (A2-2).
  • R 55 Is -SO 3 ⁇ Or -SO 2 NHR 28 Represents.
  • R 26 , R 28 , X and a represent the same meaning as described above.
  • Examples of the compound (A2) include formula (1-1) to formula (1-10), formula (1-3) to formula (1-15), formula (1-17) to formula (1-46).
  • R 40 represents a saturated hydrocarbon group having 1 to 20 carbon atoms, preferably a branched alkyl group having 6 to 12 carbon atoms, more preferably a 2-ethylhexyl group.
  • a commercially available xanthene dye for example, “Chugai Aminol Fast Pin RH / C” manufactured by Chugai Kasei Co., Ltd., “Rhodamin 6G” manufactured by Taoka Chemical Industry Co., Ltd.
  • xanthene dye for example, “Chugai Aminol Fast Pin RH / C” manufactured by Chugai Kasei Co., Ltd., “Rhodamin 6G” manufactured by Taoka Chemical Industry Co., Ltd.
  • the total content of the compound (A1) and the compound (A2) is preferably 1% by mass or more and 99% by mass or less, more preferably 1% by mass or more and 80% by mass or less in the colorant (A), and 3% by mass or more. 70 mass% or less is more preferable.
  • the mass ratio of the compound (A1) to the compound (A2) is preferably 1: 9 to 9: 1, and more preferably 3: 7 to 7: 3.
  • Colorant (A) may contain both a dye different from compound (A1) and compound (A2). Examples of the dye include oil-soluble dyes, acid dyes, dyes such as amine salts of acid dyes and sulfonamides of acid dyes.
  • the dyes are classified as dyes in the Color Index (published by The Society of Dyer's and Colorists). And known dyes described in Dyeing Notes (Color Dyeing). Specifically, C.I. I. Solvent Yellow 4 (hereinafter, description of CI Solvent Yellow is omitted, and only the number is described), 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99 162; C. I. Solvent Red 45 (hereinafter, the description of CI Solvent Red is omitted, and only the number is described), 49, 125, 130; C. I. Solvent Orange 2 (hereinafter, CI Solvent Orange is omitted, and only numbers are described), 7, 11, 15, 26, 56; I.
  • Solvent dyes C. I. Acid Yellow 1 (hereinafter, CI Acid Yellow is omitted, and only numbers are described) 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221 228, 230, 232, 235, 238, 240, 242, 243, 251; C.
  • Acid Red 1 (hereinafter, CI Acid Red is omitted, and only the number is described) 4, 8, 14, 17, 18, 26, 27, 29, 31, 34, 35, 37 , 42, 44, 50, 51, 52, 57, 66, 73, 80, 87, 88, 91, 92, 94, 97, 103, 111, 114, 129, 133, 134, 138, 143, 145, 150 151, 158, 176, 182, 183, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280 281, 195, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 394, 401, 412, 417, 41 , 422, 426; C.
  • Acid Orange 6 (hereinafter, CI Acid Orange is omitted, and only the number is described), 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64 74, 75, 94, 95, 107, 108, 169, 173; C.
  • Acid Violet 6B (hereinafter, CI Acid Violet is omitted and only the number is described), 7, 9, 17, 19; I. Acid dyes, C. I.
  • Direct Yellow 2 (hereinafter, description of CI Direct Yellow is omitted, and only the number is described), 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141; C. I.
  • Direct Red 79 (hereinafter, the description of CI Direct Red is omitted and only the number is described), 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250; C.
  • Direct Orange 34 (hereinafter, the description of CI Direct Orange is omitted, and only the number is described), 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70 96, 97, 106, 107; C.
  • I. Direct Violet 47 (hereinafter, the description of CI Direct Violet is omitted and only the number is described), 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89 , 90, 93, 95, 96, 103, 104;
  • Direct dyes C. I. Modern Yellow 5 (hereinafter, description of CI Modern Yellow is omitted, and only the number is described), 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45 56, 61, 62, 65; C. I.
  • Modern Tread 1 (hereinafter, CI Modern Tread is omitted, and only numbers are described) 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22 23, 24, 25, 26, 30, 32, 33, 36, 37, 38, 39, 41, 43, 45, 46, 48, 53, 56, 63, 71, 74, 85, 86, 88, 90 94, 95; C.
  • Modern Orange 3 (hereinafter, CI Modern Orange is omitted, and only the number is described) 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; C. I.
  • Modern Violet 1 (hereinafter, description of CI Modern Violet is omitted, and only the number is described) 2, 4, 5, 7, 14, 22, 24, 30, 31, 32, 37 , 40, 41, 44, 45, 47, 48, 53, 58; I.
  • Examples include modern dyes.
  • the colorant (A) may further contain a pigment.
  • pigments include organic pigments such as C.I. I. Violet color pigments such as CI Pigment Violet 1 (hereinafter, CI Pigment Violet is omitted and only the number is described), 19, 23, 29, 32, 36, 38, etc .; I.
  • Pigment Yellow 1 (hereinafter, CI Pigment Yellow is omitted and only the number is described) 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83 86, 93, 94, 109, 110, 117, 125, 128, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 194, 214, etc .;
  • Pigment Orange 13 (hereinafter, CI Pigment Orange is omitted and only the number is described), 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65 Orange pigments such as 71, 73; I.
  • Pigment Red 9 (hereinafter, CI Pigment Red is omitted and only the number is described), 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192 , 209, 215, 216, 224, 242, 254, 255, 264, 265, and the like.
  • the pigments C.I. I. Pigment yellow 138, 139, 150, C.I. I. It is preferable to contain at least one selected from CI Pigment Red 177, 242, and 254.
  • the transmission spectrum can be easily optimized and the chemical resistance is improved.
  • These pigments may be used alone or in combination of two or more.
  • the organic pigment is finely divided by rosin treatment, surface treatment using a pigment derivative having an acidic group or basic group introduced, graft treatment to the pigment surface with a polymer compound, sulfuric acid atomization method, etc. Or a cleaning process using an organic solvent or water for removing impurities, an ionic impurity removing process using an ion exchange method, or the like may be performed.
  • the organic pigment preferably has a uniform particle size.
  • a pigment dispersant may be included in the colored curable resin composition of the present invention.
  • pigment dispersant examples include cationic, anionic, nonionic, amphoteric, polyester, polyamine, and acrylic surfactants. These pigment dispersants may be used alone or in combination of two or more.
  • KP manufactured by Shin-Etsu Chemical Co., Ltd.
  • Floren manufactured by Kyoeisha Chemical Co., Ltd.
  • Solsperse manufactured by Geneca Co., Ltd.
  • EFKA manufactured by BASF
  • Ajispur Ajinomoto Fine
  • Disperbyk Bic Chemie
  • the amount used is preferably 100% by mass, more preferably 5% by mass or more and 50% by mass or less, based on the pigment.
  • the content of the colorant (A) is preferably 5 to 60% by mass, more preferably 8 to 55% by mass, and further preferably 10 to 10% by mass with respect to the solid content in the colored curable resin composition. 50% by mass.
  • solid content means the sum total of the component except a solvent in colored curable resin composition.
  • the colored curable resin composition of the present invention may further contain a boron complex (F).
  • a boron complex (F) include an anion represented by the following formula (4). [W in Formula (4) 1 , W 2 Each independently represents a group formed by releasing protons from two monovalent proton-donating substituents. ] In the anion represented by the formula (4), the two monovalent proton-donating substituents from which protons are released may be catechol which may have a substituent or may have a substituent.
  • 3-nitrosalicylic acid 4-trifluoromethylsalicylic acid, 3,5-di-tert-butylsalicylic acid, 3,5-dibromosalicylic acid, 3,5-dichlorosalicylic acid, 3,5,6-trichlorosalicylic acid, 3-hydroxy Salicylic acid (2,3-dihydroxybenzoic acid), 4-hydroxysalicylic acid (2,4-dihydroxybenzoic acid), 5-hydroxysalicylic acid (2,5-dihydroxybenzoic acid), 6-hydroxysalicylic acid (2,6-dihydroxybenzoic acid) Acid) and the like.
  • the benzylic acid that may have the above substituent include: Etc.
  • Examples of the mandelic acid which may have the above substituent include, for example, Etc.
  • Examples of the anion represented by the formula (4) include anions represented by the following formula (A) such as anion (BC-1) to anion (BC-24), and anions (BC-25) to anion (BC -28).
  • the anion (BC-1) to anion (BC-24) are R 61 , R 62 , R 63 And R 64 As having the substituents shown in Table 1.
  • an anion represented by Formula (4) an anion (BC-1), an anion (BC-2), an anion (BC-3), an anion (BC-25), an anion (BC-26), an anion (BC-27) is preferable, an anion (BC-1), an anion (BC-2), and an anion (BC-25) are more preferable, and an anion (BC-1) and an anion (BC-2) are more preferable.
  • an anion (BC-1), an anion (BC-2), and an anion (BC-25) are more preferable
  • an anion (BC-1) and an anion (BC-2) are more preferable.
  • the content of the boron complex (F) is preferably 0.1 parts by mass or more and 20 parts by mass or less, and more preferably 0.5 parts by mass or more and 10 parts by mass or less with respect to 100 parts by mass of the colorant (A).
  • ⁇ Zinc complex (G)> The colored curable resin composition of the present invention may contain a zinc complex (G).
  • Examples of the zinc complex (G) include a zinc complex represented by the formula (5). [In formula (5), R 71 ⁇ R 74 Each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a hydroxyl group.
  • R in formula (5) 71 ⁇ R 74 examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, and tert-butyl group.
  • Specific examples of the zinc complex represented by the formula (5) include complexes having the substituents shown in Table 2.
  • (5) -18 is preferable from the viewpoint of improving heat resistance. 0.1 mass% or more and 30 mass% or less are preferable with respect to a coloring agent (A), and, as for content of a zinc complex (G), 0.5 mass% or more and 15 mass% or less are more preferable.
  • the colored curable resin composition of the present invention contains a resin (B). Although it does not specifically limit as resin (B), It is preferable that it is alkali-soluble resin.
  • the resin (B) include the following resins [K1] to [K4].
  • [K1] a monomer (a) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(a)”), an unsaturated carboxylic acid and an unsaturated carboxylic acid A copolymer with at least one (b) selected from the group consisting of anhydrides (hereinafter sometimes referred to as “(b)”).
  • the resin (B) contains a structural unit derived from (a)
  • the reliability of the resulting colored pattern such as heat resistance and chemical resistance, can be further increased.
  • (A) has, for example, a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring (oxolane ring)) and an ethylenically unsaturated bond. It refers to a polymerizable compound.
  • (A) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth) acryloyloxy group.
  • (meth) acrylic acid represents at least one selected from the group consisting of acrylic acid and methacrylic acid.
  • (a) examples include a monomer (a1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(a1)”), and a single monomer having an oxetanyl group and an ethylenically unsaturated bond.
  • Monomer (a2) hereinafter sometimes referred to as “(a2)”
  • monomer (a3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(a3)”), and the like Can be mentioned.
  • (A1) has, for example, a monomer (a1-1) having a structure obtained by epoxidizing a chain olefin (hereinafter sometimes referred to as “(a1-1)”), and a structure obtained by epoxidizing a cyclic olefin.
  • monomer (a1-2) hereinafter may be referred to as “(a1-2)”.
  • glycidyl (meth) acrylate ⁇ -methylglycidyl (meth) acrylate, ⁇ -ethylglycidyl (meth) acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p -Vinylbenzyl glycidyl ether, ⁇ -methyl-o-vinylbenzyl glycidyl ether, ⁇ -methyl-m-vinylbenzyl glycidyl ether, ⁇ -methyl-p-vinylbenzyl glycidyl ether, 2,3-bis (glycidyloxymethyl) styrene 2,4-bis (glycidyloxymethyl) styrene, 2,5-bis (glycidyloxymethyl) styrene, 2,6-bis (glycidyl vinyl g
  • Examples of (a1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celoxide 2000; manufactured by Daicel Chemical Industries, Ltd.), 3,4-epoxycyclohexylmethyl (meth) acrylate (for example, Cyclomer A400 (manufactured by Daicel Chemical Industries, Ltd.), 3,4-epoxycyclohexylmethyl (meth) acrylate (for example, Cyclomer M100; manufactured by Daicel Chemical Industries, Ltd.), represented by formula (I) Examples thereof include compounds and compounds represented by formula (II).
  • R a And R b Independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxy group.
  • X 1 And X 2 are independently of each other a single bond, -R c -, * -R c -O-, * -R c -S-, * -R c -NH- is represented.
  • R c Represents an alkanediyl group having 1 to 6 carbon atoms. * Represents a bond with O.
  • Examples of the alkyl group having 1 to 4 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, and tert-butyl group.
  • Examples of the alkyl group in which a hydrogen atom is substituted with hydroxy include hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 1-hydroxy Examples include a -1-methylethyl group, a 2-hydroxy-1-methylethyl group, a 1-hydroxybutyl group, a 2-hydroxybutyl group, a 3-hydroxybutyl group, and a 4-hydroxybutyl group.
  • R a And R b As for, Preferably a hydrogen atom, a methyl group, a hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group is mentioned, More preferably, a hydrogen atom and a methyl group are mentioned.
  • Examples of the alkanediyl group include methylene group, ethylene group, propane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane- Examples include 1,6-diyl group.
  • X 1 And X 2 Are preferably a single bond, a methylene group, an ethylene group, or * -CH.
  • Examples of the compound represented by the formula (I) include compounds represented by the formula (I-1) to the formula (I-15).
  • Examples of the compound represented by the formula (II) include compounds represented by the formula (II-1) to the formula (II-15).
  • Formula (II-1), Formula (II-3), Formula (II-5), Formula (II-7), Formula (II-9), Formula (II-11) to Formula (II-15) Is mentioned. More preferably, Formula (II-1), Formula (II-7), Formula (II-9), and Formula (II-15) are mentioned.
  • the compound represented by the formula (I) and the compound represented by the formula (II) can be used alone. They can also be mixed in any ratio. In the case of mixing, the mixing ratio is a molar ratio, preferably 5:95 to 95: 5, more preferably 10:90 to 90:10, particularly preferably 20:80 in the formula (I): formula (II). ⁇ 80: 20.
  • the monomer (a2) having an oxetanyl group and an ethylenically unsaturated bond a monomer having an oxetanyl group and a (meth) acryloyloxy group is more preferable.
  • (a2) 3-methyl-3-methacryloyloxymethyl oxetane, 3-methyl-3-acryloyloxymethyl oxetane, 3-ethyl-3-methacryloyloxymethyl oxetane, 3-ethyl-3-acryloyloxymethyl oxetane , 3-methyl-3-methacryloyloxyethyl oxetane, 3-methyl-3-acryloyloxyethyl oxetane, 3-ethyl-3-methacryloyloxyethyl oxetane, 3-ethyl-3-acryloyloxyethyl oxetane, and the like.
  • the monomer (a3) having a tetrahydrofuryl group and an ethylenically unsaturated bond a monomer having a tetrahydrofuryl group and a (meth) acryloyloxy group is more preferable.
  • Specific examples of (a3) include tetrahydrofurfuryl acrylate (for example, Biscoat V # 150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like.
  • (A) is preferably (a1) from the viewpoint that the reliability of the resulting colored pattern, such as heat resistance and chemical resistance, can be further increased. Furthermore, (a1-2) is more preferable in that the storage stability of the colored curable resin composition is excellent.
  • (b) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid; Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyl Unsaturated dicarboxylic acids such as tetrahydrophthalic acid and 1,4-cyclohexene dicarboxylic acid; Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo [2.2.1] hept-2-ene, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene, 5-carboxy-5-methylbicyclo [2.2.1] hept-2-ene, 5-carboxy-5-methylbic
  • acrylic acid, methacrylic acid, maleic anhydride and the like are preferable from the viewpoint of copolymerization reactivity and solubility in an aqueous alkali solution.
  • examples of (c) include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, and 2-ethylhexyl (meth).
  • the ratio of the structural units derived from each is preferably in the following range among all the structural units constituting the resin [K1].
  • Resin [K1] is, for example, a method described in the document “Experimental Methods for Polymer Synthesis” (Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st edition, published on March 1, 1972) and the document Can be produced with reference to the cited references described in 1.
  • oxygen is substituted with nitrogen, thereby deoxidizing, stirring, heating, and keeping warm.
  • the polymerization initiator, the solvent, and the like used here are not particularly limited, and any of those usually used in the field can be used.
  • azo compounds (2,2′-azobisisobutyronitrile, 2,2′-azobis (2,4-dimethylvaleronitrile), etc.
  • organic peroxides benzoyl peroxide, etc.
  • Any solvent may be used as long as it dissolves each monomer, and a solvent described later can be used as a solvent for the colored curable resin composition.
  • the obtained copolymer may use the solution after reaction as it is, a concentrated or diluted solution may be used, and it took out as solid (powder) by methods, such as reprecipitation. Things may be used.
  • the solution after the reaction can be used as it is, and the manufacturing process can be simplified.
  • the ratio of the structural units derived from each is preferably in the following range among all the structural units constituting the resin [K2].
  • the ratio of the structural units derived from each is preferably in the following range among all the structural units constituting the resin [K3].
  • Resin [K3] can be produced, for example, in the same manner as the method described for producing resin [K1].
  • the resin [K4] is obtained by obtaining a copolymer of (b) and (c) and adding the carboxy group of (c) to the cyclic ether having 2 to 4 carbon atoms of (a). Can do. First, a copolymer of (b) and (c) is produced in the same manner as described in [K1].
  • the ratio of the structural units derived from each is preferably in the following range among all the structural units constituting the copolymer of (b) and (c).
  • the carboxy group and / or part of the carboxylic acid anhydride contained in the structural unit derived from (b) in the copolymer is reacted with a cyclic ether having 2 to 4 carbon atoms which (a) has. .
  • the atmosphere in the flask is replaced by nitrogen to air, and (a) a reaction catalyst of a carboxy group and a cyclic ether (for example, tris (dimethylaminomethyl) phenol Etc.) to 0.001 to 5% by mass with respect to the total amount of (a) to (c), and a polymerization inhibitor (for example, hydroquinone etc.) to the total amount of (a) to (c).
  • Resin [K4] can be obtained by placing 001-5 mass% in a flask and reacting at 60-130 ° C. for 1-10 hours, for example.
  • the reaction conditions such as the charging method, reaction temperature, and time can be appropriately adjusted in consideration of the production equipment and the amount of heat generated by polymerization.
  • the charging method and the reaction temperature can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, and the like.
  • the amount of (a) used is preferably 0.05 to 0.8 mol, more preferably 0.1 to 0.75 mol, and still more preferably 0. 15 to 0.7 mol. By setting it as this range, there exists a tendency for the balance of storage stability, developability, solvent resistance, heat resistance, mechanical strength, and sensitivity to become favorable.
  • the resin (B) include 3,4-epoxycyclohexylmethyl (meth) acrylate / (meth) acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0. 2.6 ] Resin such as decyl acrylate / (meth) acrylic acid copolymer [K1]; glycidyl (meth) acrylate / benzyl (meth) acrylate / (meth) acrylic acid copolymer, glycidyl (meth) acrylate / styrene / (meta ) Acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 2.6 ] Resin [K2] such as decyl acrylate / (meth) acrylic acid / N-cyclohexylmaleimide copolymer, 3-methyl-3- (meth) acryloyloxymethyloxetane / (meth) acrylic acid / sty
  • resin [K1] and resin [K2] are preferable, resin [K1] is more preferable, and 3,4-epoxytricyclo [5.2.1.0].
  • 2.6 A decyl acrylate / (meth) acrylic acid copolymer is more preferable.
  • the polystyrene equivalent weight average molecular weight of the resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and further preferably 5,000 to 35,000. Particularly preferred is 6,000 to 30,000, and particularly preferred is 7,000 to 28,000. When the molecular weight is in the above range, the coating film hardness is improved, the residual film ratio is high, the solubility of the unexposed portion in the developer is good, and the resolution tends to be improved.
  • the molecular weight distribution [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (B) is preferably 1.1 to 6, and more preferably 1.2 to 4.
  • the acid value of the resin (B) is preferably 50 to 150 mg-KOH / g, more preferably 60 to 135 mg-KOH / g, and still more preferably 70 to 135 mg-KOH / g.
  • the acid value is a value measured as the amount (mg) of potassium hydroxide necessary to neutralize 1 g of the resin (B), and can be determined by titration with an aqueous potassium hydroxide solution, for example.
  • the content of the resin (B) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and further preferably 17 to 55% by mass with respect to the solid content of the colored curable resin composition. %.
  • the content of the resin (B) is in the above range, a pattern can be formed and the resolution and the remaining film rate tend to be improved.
  • the photopolymerizable compound (C) is a compound that can be polymerized by an active radical, an acid, or the like generated from the photopolymerization initiator (D) when irradiated with light, and for example, a polymerizable ethylenically unsaturated bond
  • the compound etc. which have these are mentioned, Preferably a (meth) acrylic acid ester compound is mentioned.
  • the photopolymerizable compound (C) is preferably a photopolymerizable compound having three or more ethylenically unsaturated bonds.
  • Examples of such a photopolymerizable compound include pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, dipentaerythritol pentaacrylate, dipentaerythritol pentamethacrylate, dipentaerythritol hexaacrylate, dipentaerythritol hexamethacrylate, and the like.
  • the photopolymerizable compound (C) may be used alone or in combination of two or more.
  • the content of the photopolymerizable compound (C) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and still more preferably based on the solid content of the colored curable resin composition.
  • the colored curable resin composition of the present invention contains a photopolymerization initiator (D).
  • a photopolymerization initiator (D) if it is a compound which generate
  • the photopolymerization initiator (D) is preferably a compound that generates an active radical by the action of light, and is at least one selected from the group consisting of alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, oxime compounds, and biimidazole compounds. Is more preferable, and a photopolymerization initiator containing an oxime compound is more preferable.
  • alkylphenone compound include diethoxyacetophenone, 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one, 2-dimethylamino-1- (4-morpholinophenyl) -2-benzyl.
  • 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one, 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutan-1-one, etc. can be mentioned.
  • Commercial products such as Irgacure 369, 907 (above, manufactured by BASF) may be used.
  • acylphosphine oxide compound examples include 2,4,6-trimethylbenzoyldiphenylphosphine oxide.
  • Commercial products such as Irgacure 819 (manufactured by BASF) may be used.
  • oxime compounds include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2.
  • biimidazole compound examples include 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetraphenylbiimidazole and 2,2′-bis (2,3-dichlorophenyl) -4,4.
  • Examples thereof include imidazole compounds (for example, see JP-A-7-10913).
  • 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetraphenylbiimidazole, 2,2′-bis (2,3-dichlorophenyl) -4,4 ′, 5 Examples include 5'-tetraphenylbiimidazole and 2,2'-bis (2,4-dichlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole.
  • Examples of the acid generator that generates an acid by light include 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4 -Onium salts such as acetoxyphenyl methyl benzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, diphenyliodonium hexafluoroantimonate, Examples thereof include nitrobenzyl tosylate and benzoin tosylate.
  • the photopolymerization initiator (D) may be a compound that simultaneously generates an active radical and an acid by light, such as a triazine compound.
  • benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether; benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl Benzophenone compounds such as -4'-methyldiphenyl sulfide, 3,3 ', 4,4'-tetra (tert-butylperoxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone; 9,10-phenanthrenequinone Quinone compounds such as 2-ethylanthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl ether, benzoin ethyl
  • the content of the photopolymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 with respect to 100 parts by mass of the total amount of the resin (B) and the photopolymerizable compound (C). ⁇ 20 parts by mass.
  • the content of the photopolymerization initiator is within the above range, the sensitivity is increased, the exposure time is shortened, and the productivity is improved.
  • the photopolymerization initiation assistant (D1) is usually used in combination with the photopolymerization initiator (D), and is a compound used for accelerating the polymerization of the photopolymerizable compound initiated by the photopolymerization initiator, Or it is a sensitizer.
  • Examples of the photopolymerization initiation assistant (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.
  • amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 4- 2-ethylhexyl dimethylaminobenzoate, N, N-dimethylparatoluidine, 4,4′-bis (dimethylamino) benzophenone (commonly known as Michler's ketone), 4,4′-bis (diethylamino) benzophenone, 4,4′-bis ( Ethylmethylamino) benzophenone and the like, and 4,4′-bis (diethylamino) benzophenone is preferred.
  • EAB-F Hodogaya Chemical Co., Ltd.
  • alkoxyanthracene compound examples include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, and 9,10-dibutoxy.
  • Anthracene, 2-ethyl-9,10-dibutoxyanthracene, etc. are mentioned.
  • thioxanthone compound examples include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone and the like.
  • Carboxylic acid compounds include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N -Phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid and the like.
  • the photopolymerization initiation assistant (D1) may be used alone or in combination of two or more.
  • the amount used is preferably 0.01 to 50 parts by mass with respect to 100 parts by mass of the total amount of the resin (B) and the photopolymerizable compound (C). More preferably, it is 0.1 to 40 parts by mass.
  • the amount is preferably 0.01 to 10 mol, more preferably 0.01 to 5 mol, per 1 mol of the photopolymerization initiator (D).
  • the amount of the polymerization initiation assistant (D1) is within this range, the pattern can be formed with higher sensitivity, and the productivity of the pattern tends to be improved.
  • the colored curable resin composition of the present invention contains a solvent (E).
  • Solvent (E) is not particularly limited, and a solvent usually used in this field can be used.
  • ester solvents solvents containing —COO—
  • ether solvents other than ester solvents solvents containing —O—
  • ether ester solvents solvents containing —COO— and —O—
  • ketones other than ester solvents A solvent (solvent containing —CO—), an alcohol solvent, an aromatic hydrocarbon solvent, an amide solvent, dimethyl sulfoxide, or the like can be selected and used.
  • ester solvents methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate , Methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, ⁇ -butyrolactone and the like.
  • Ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, 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, die Glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, methyl anisole, and the like.
  • ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3-ethoxy Ethyl propionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, Ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl acetate Le acetate, propylene glycol monopropyl ether
  • ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.
  • Etc. examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.
  • aromatic hydrocarbon solvents include benzene, toluene, xylene, mesitylene and the like.
  • amide solvent examples include N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and the like. These solvents may be used alone or in combination of two or more. Of the above solvents, organic solvents having a boiling point of 120 ° C. or more and 180 ° C. or less at 1 atm are preferable from the viewpoints of coating properties and drying properties.
  • propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone, N , N-dimethylformamide, N-methylpyrrolidone and the like are preferable, and propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, ethyl lactate, ethyl 3-ethoxypropionate and the like are more preferable.
  • these solvents are included, the flatness during application is excellent.
  • the content of the solvent (E) in the colored curable resin composition is preferably 70 to 95% by mass, more preferably 75 to 92% by mass with respect to the colored curable resin composition.
  • the solid content of the colored curable resin composition is preferably 5 to 30% by mass, more preferably 8 to 25% by mass.
  • surfactant (H) examples include silicone surfactants, fluorine surfactants, and silicone surfactants having a fluorine atom. These may have a polymerizable group in the side chain.
  • silicone surfactants include surfactants having a siloxane bond.
  • fluorosurfactant examples include surfactants having a fluorocarbon chain. Specifically, Florard (trade name) FC430, FC431 (Sumitomo 3M Co., Ltd.), MegaFuck (trade name) F142D, F171, F172, F173, F177, F183, F183, R30, the same RS-718-K (manufactured by DIC Corporation), EFtop (trade name) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronics Chemical), Surflon (tradename) S381, S382, SC101, SC105 (Asahi Glass Co., Ltd.), E5844 (Daikin Fine Chemical Laboratory Co., Ltd.) and the like.
  • Florard trade name
  • FC430 Fluorocarbon chain
  • FC431 Suditomo 3M Co., Ltd.
  • MegaFuck trade name
  • F142D F171, F172, F173, F177, F183, F183, R30
  • silicone-based surfactant having a fluorine atom examples include surfactants having a siloxane bond and a fluorocarbon chain. Specifically, Megafac (registered trademark) R08, BL20, F475, F477, F443 (manufactured by DIC Corporation) and the like can be mentioned. These surfactants may be used alone or in combination of two or more.
  • the content of the surfactant (H) is preferably 0.001% by mass or more and 0.2% by mass or less, preferably 0.002% by mass or more and 0.1% by mass with respect to the colored curable resin composition. Hereinafter, it is more preferably 0.01% by mass or more and 0.05% by mass or less.
  • the colored curable resin composition of the present invention comprises a colorant (A), an alkali-soluble resin (B), a photopolymerizable compound (C), a photopolymerization initiator (D), a solvent (E), and a surfactant (H ), A colored pattern having excellent coatability and excellent solvent resistance and spectroscopy can be obtained.
  • the colored curable resin composition of the present invention includes various additives such as fillers, other polymer compounds, adhesion promoters, antioxidants, ultraviolet absorbers, light stabilizers, chain transfer agents, and the like as necessary. May be included.
  • the colored curable resin composition of the present invention is first formed on a substrate or another resin layer (for example, on the substrate). Applied to another colored curable resin composition layer, etc.), removing / drying volatile components such as a solvent to form a colored layer, exposing the colored layer through a photomask, and developing Examples thereof include a photolithographic method and an inkjet method.
  • the film thickness of the coating film in this case is not particularly limited and can be appropriately adjusted depending on the material used, application, etc., and is, for example, 0.1 to 30 ⁇ m, preferably 1 to 20 ⁇ m, more preferably 1 to 6 ⁇ m. .
  • Examples of the coating method of the colored curable resin composition include an extrusion coating method, a direct gravure coating method, a reverse gravure coating method, a CAP coating method, and a die coating method.
  • coat using coaters such as a dip coater, a bar coater, a spin coater, a slit & spin coater, and a slit coater (it may also be called a die coater, a curtain flow coater, and a spinless coater).
  • Examples of solvent removal / drying include natural drying, ventilation drying, reduced pressure drying, and heat drying.
  • the specific drying temperature is preferably 10 to 120 ° C, more preferably 25 to 100 ° C.
  • the drying time is preferably 10 seconds to 60 minutes, and more preferably 30 seconds to 30 minutes.
  • the drying under reduced pressure is preferably performed at a temperature of 20 to 25 ° C. under a pressure of 50 to 150 Pa.
  • the dried coating film is exposed through a photomask for forming a target pattern.
  • the pattern shape on the photomask at this time is not particularly limited, and a pattern shape corresponding to the intended application is used.
  • As the light source used for exposure a light source that generates light having a wavelength of 250 to 450 nm is preferable.
  • Specific examples include mercury lamps, light-emitting diodes, metal halide lamps, halogen lamps, etc., which can be cut using a filter that cuts a specific wavelength range, or selectively extracted using a bandpass filter that extracts a specific wavelength range. And may be exposed. It is preferable to use an apparatus such as a mask aligner or a stepper because the entire exposed surface can be irradiated with parallel rays uniformly and accurate alignment between the mask and the substrate can be performed. After exposure, a pattern can be obtained by contacting with a developing solution to dissolve a predetermined portion, for example, an unexposed portion, and developing.
  • the developer examples include aqueous solutions of alkaline compounds (potassium hydroxide, sodium carbonate, tetramethylammonium hydroxide, etc.).
  • the developer may contain a surfactant.
  • the developing method may be any of paddle method, dipping method, spray method and the like. Further, the substrate may be tilted at an arbitrary angle during development. After development, it is preferable to wash with water. Further, post-baking may be performed if necessary. Post baking is preferably in the range of 150 to 230 ° C. and 10 to 240 minutes, for example. According to the colored curable resin composition of the present invention, it is possible to obtain a coating film, a pattern and a high quality color filter having good brightness and contrast.
  • display devices including these color filters or patterns as a part of their components, for example, all known devices related to various colored images, such as liquid crystal display devices, organic EL devices, solid-state imaging devices, etc. It can be utilized in the form of.
  • display devices including these color filters or patterns as a part of their components, for example, all known devices related to various colored images, such as liquid crystal display devices, organic EL devices, solid-state imaging devices, etc. It can be utilized in the form of.
  • “%” and “part” representing the content or amount used are based on mass unless otherwise specified.
  • the structure of the compound was confirmed by mass spectrometry (LC; Agilent 1200 type, MASS; Agilent LC / MSD type).
  • Synthesis Example 1 After adding 65 parts of water to 7.5 parts of 2-amino-4-methylsulfonyl-6-nitrophenol (CAS No.
  • Resin B1 has the structural units shown below.
  • the measurement of the weight average molecular weight (Mw) and the number average molecular weight (Mn) of the resin obtained in the synthesis example was performed using the GPC method under the following conditions.
  • Flow rate 1.0 mL / min
  • Detector RI calibration reference material; TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)
  • the ratio of weight average molecular weight and number average molecular weight (Mw / Mn) in terms of polystyrene obtained above was defined as molecular weight distribution.
  • Example 1 and Comparative Example 1 Each component was mixed so that it might become a composition shown in Table 3, and the red colored curable resin composition was obtained.
  • the pigment is a pigment dispersant and E-1 2) It was mixed with propylene glycol monomethyl ether acetate in the amount indicated in the column and dispersed in advance.
  • E-1 2) Represents the total content of propylene glycol monomethyl ether acetate.
  • each component represents the following.
  • resin (B) showed the mass part of solid content conversion.
  • the distance between the composition layer on the substrate and the quartz glass photomask having a pattern is set to 100 ⁇ m, and an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.) is used in an air atmosphere at 150 mJ / cm. 2 was irradiated with light at an exposure amount (365 nm reference).
  • TME-150RSK an exposure machine
  • a photomask a mask on which a 100 ⁇ m line and space pattern was formed was used. After light irradiation, the coating film was immersed and developed in an aqueous developer containing 0.12% nonionic surfactant and 2% sodium carbonate at 23 ° C.
  • Example 2 and Comparative Example 2 Each component was mixed so that it might become a composition shown in Table 5, and the red colored curable resin composition was obtained.
  • the pigment is a pigment dispersant and E-1 2) It was mixed with propylene glycol monomethyl ether acetate in the amount indicated in the column and dispersed in advance.
  • E-1 2) Represents the total content of propylene glycol monomethyl ether acetate.
  • each component represents the following.
  • resin (B) showed the mass part of solid content conversion.
  • Compound (A3) Compound represented by the following formula
  • Compound (A1) Compound represented by formula (z-2) Pigment: C.I. I.
  • each component represents the following.
  • resin (B) showed the mass part of solid content conversion.
  • Compound (A2) Compound represented by Formula (1-37)
  • Compound (A1) Compound represented by formula (z-2) Pigment (A3): C.I. I. Pigment Red 254 Pigment (A4): C.I. I. Pigment Red 177 Pigment (A5): C.I. I. Pigment Red 242 Pigment (A6): C.I. I.
  • the pigment is a pigment dispersant and E-1 2) It was mixed with propylene glycol monomethyl ether acetate in the amount indicated in the column and dispersed in advance.
  • E-1 2) Represents the total content of propylene glycol monomethyl ether acetate.
  • each component represents the following.
  • resin (B) showed the mass part of solid content conversion.
  • a color filter excellent in brightness and contrast can be produced.

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Abstract

L'invention concerne une composition de résine durcissable colorée qui comprend un colorant (A), une résine (B) un composé photopolymérisable (C), un photo-initiateur de polymérisation (D) et un solvant (E), dans lequel le colorant (A) comprend à la fois un composé représenté par la formule (A1) et un composé représenté par la formule (A2). Cette composition de résine durcissable colorée présente une excellente luminosité et du contraste.
PCT/JP2014/065522 2013-06-07 2014-06-05 Composition de résine durcissable colorée Ceased WO2014196660A1 (fr)

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JP2017120379A (ja) * 2015-12-29 2017-07-06 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. 着色感光性樹脂組成物、カラーフィルター及びこれを具備した画像表示装置
JP2017226814A (ja) * 2016-06-20 2017-12-28 東友ファインケム株式会社Ｄｏｎｇｗｏｏ Ｆｉｎｅ−Ｃｈｅｍ Ｃｏ．， Ｌｔｄ． 化合物及び着色硬化性樹脂組成物
JP2020158761A (ja) * 2019-03-25 2020-10-01 住友化学株式会社 着色硬化性樹脂組成物、カラーフィルタ及び固体撮像素子

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CN108783773B (zh) * 2018-07-19 2021-05-07 浙江伟星实业发展股份有限公司 一种增加塑钢拉链链牙上色牢度的处理工艺及塑钢拉链
TWI817068B (zh) * 2020-12-29 2023-10-01 住華科技股份有限公司 應用著色樹脂組成物之光阻結構、彩色濾光片和顯示裝置

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JP2017120379A (ja) * 2015-12-29 2017-07-06 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. 着色感光性樹脂組成物、カラーフィルター及びこれを具備した画像表示装置
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