WO2014196661A1 - Composition de résine colorante durcissable - Google Patents

Composition de résine colorante durcissable Download PDF

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Publication number
WO2014196661A1
WO2014196661A1 PCT/JP2014/065523 JP2014065523W WO2014196661A1 WO 2014196661 A1 WO2014196661 A1 WO 2014196661A1 JP 2014065523 W JP2014065523 W JP 2014065523W WO 2014196661 A1 WO2014196661 A1 WO 2014196661A1
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Prior art keywords
group
carbon atoms
resin composition
formula
curable resin
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PCT/JP2014/065523
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English (en)
Japanese (ja)
Inventor
鈴木　智也
芦田　徹
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住友化学株式会社
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Application filed by 住友化学株式会社 filed Critical 住友化学株式会社
Priority to CN201480032415.5A priority Critical patent/CN105264442B/zh
Priority to JP2015521519A priority patent/JP6454273B2/ja
Priority to KR1020157033624A priority patent/KR102284012B1/ko
Publication of WO2014196661A1 publication Critical patent/WO2014196661A1/fr

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    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0084—Dispersions of dyes
    • C09B67/0085—Non common dispersing agents
    • C09B67/009—Non common dispersing agents polymeric dispersing agent
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/322—Pigment inks
    • 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
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • 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 colored cured product having better brightness and contrast and a color filter including the same.
  • the present invention provides the following [1] to [9].
  • a colorant (A), a resin (B), a photopolymerizable compound (C), a photopolymerization initiator (D), and a solvent (E) and the colorant (A) comprises (i) and ( A colored curable resin composition which is a colorant comprising at least one selected from the group consisting of ii) and (iii).
  • R 21 to R 24 each independently represents a hydrogen atom, an aliphatic hydrocarbon group having 1 to 8 carbon atoms or a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms, The hydrogen atom contained in the aliphatic hydrocarbon group and the aromatic hydrocarbon group may be substituted with a hydroxy group, —OR 33, or a halogen atom.
  • R 33 represents a monovalent aliphatic hydrocarbon group having 1 to 8 carbon atoms.
  • R 25 and R 26 each independently represents a hydrogen atom or a methyl group.
  • R 27 represents an ethylene group, propane-1,3-diyl or propane-1,2-diyl group.
  • R 28 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • n represents an integer of 1 to 4. When n is an integer greater than or equal to 2, several R ⁇ 27 > may mutually be same or different.
  • (Ii) Compound represented by formula (A1) [In Formula (A1), 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.
  • Colorant (A) is a colorant comprising (i), (ii), and (iii) The colored curable resin composition according to [1].
  • [3] The colored curable resin composition according to [1], wherein the colorant (A) is a colorant containing (i) and (ii).
  • 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.
  • F boron complex
  • G zinc complex
  • the colored curable resin composition according to [1] to [6] wherein M 1 is Cr.
  • a display device including the color filter according to [8].
  • 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). Includes (i) and at least one selected from the group consisting of (ii) and (iii).
  • (I) Compound represented by formula (A2) (hereinafter sometimes referred to as “compound (A2)”)
  • R 21 ⁇ R 24 Each independently represents a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 10 carbon atoms or a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms, and the aliphatic hydrocarbon group and the aromatic Hydrogen atom contained in the group hydrocarbon group is a hydroxy group, -OR 33 Alternatively, it may be substituted with a halogen atom.
  • R 33 Represents a monovalent aliphatic hydrocarbon group having 1 to 8 carbon atoms.
  • R 25 And R 26 Each independently represents a hydrogen atom or a methyl group.
  • R 27 Represents an ethylene group, a propane-1,3-diyl group or a propane-1,2-diyl group.
  • R 28 Represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • n represents an integer of 1 to 4. When n is an integer of 2 or more, a plurality of R 27 May be the same as or different from each other.
  • Compound represented by formula (A1) (hereinafter sometimes referred to as “compound (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.
  • 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.
  • 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
  • examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group.
  • the divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms includes 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 Etc.
  • examples of the cyclohexyl group which may be substituted with an alkyl group having 1 to 4 carbon atoms include 2-methylcyclohexyl group, 2-ethylcyclohexyl group, 2-propylcyclohexyl group, 2-isopropylcyclohexyl group, Examples include 2-butylcyclohexyl group, 4-methylcyclohexyl group, 4-ethylcyclohexyl group, 4-propylcyclohexyl group, 4-isopropylcyclohexyl group, 4-butylcyclohexyl group and the like.
  • -R 31 -O-R 32 As methoxymethyl group, ethoxymethyl group, propoxymethyl group, methoxyethyl group, ethoxyethyl group, propoxyethyl group, methoxypropyl group, ethoxypropyl group, propoxypropyl group, 2-oxo-4-methoxybutyl group, octyl Examples thereof include an oxypropyl group, a 3-ethoxypropyl group, and a 3- (2-ethylhexyloxy) propyl group.
  • -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 31 -O-CO-R 32 As acetyloxymethyl group, acetyloxyethyl group, ethylcarbonyloxymethyl group, ethylcarbonyloxyethyl group, propylcarbonyloxymethyl group, propylcarbonyloxyethyl group, butylcarbonyloxymethyl group, butylcarbonyloxyethyl group, etc. Can be mentioned.
  • —SO 2 R 29 As 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) sulfamo
  • —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-tetramethylhexyl
  • R 1 ⁇ R 5 At least one of R and R 6 ⁇ R 10 At least one of which is -SO 2 R 29 It is preferable that -SO 2 R 29 A plurality of R, a plurality of R 29 May be the same as or different from each other.
  • -SO 2 R 29 Is -SO 3 H, -SO 2 NHR 30 Or -SO 2 R 32 And preferably -SO 2 R 32 It is.
  • 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 formulas (1-b1) to (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.
  • Preferable 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 between the diazonium salt (1d) 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
  • it is preferable to produce the compound by reacting with the amine (1a) having a sulfo group and then sulfonamidating the sulfo group.
  • an azo compound having a sulfo group in compound (1d) (hereinafter referred to as “compound (1s)”) is synthesized, and the sulfo group (—SO 3 H) 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.
  • compound (1s) an azo compound having a sulfo group in compound (1d)
  • halogenated thionyl compound examples 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). When water is brought into the reaction system, it is preferable to use an excessive amount of the thionyl halide compound.
  • the sulfonyl halide is carried out in a solvent.
  • the solvent examples 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.
  • compound (1s) and N, N-dialkylformamide are mixed in advance in a solvent and then a thionyl halide compound is added, heat generation can be suppressed.
  • the reaction temperature in the sulfonyl halide formation is, for example, 0 ° C. or higher, preferably 30 ° C.
  • 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 and then amine (R 30 NH 2 In the reaction mixture without isolation. 30 NH 2 ). In the case of isolation, for example, 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.
  • sulfonyl halide compounds and amines (R 30 NH 2 ) Is preferably carried out in the presence of a basic catalyst.
  • 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 ) 1.1 mol or more and 6 mol or less, preferably 1.1 mol or more and 5 mol or less with respect to 1 mol.
  • Amines (R) to sulfonyl halide compounds 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.
  • 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 techniques 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.
  • reaction mixture is added to the acid aqueous solution, it is preferably further stirred at the above temperature for about 0.5 to 2 hours.
  • the crystal collected by filtration is preferably washed with water or the like and then dried.
  • examples of the aliphatic hydrocarbon group having 1 to 8 carbon atoms include 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 and the like.
  • Examples of the monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms in the formula (A2) include a phenyl group, a toluyl group, a xylyl group, a mesityl group, a propylphenyl group, and a butylphenyl group.
  • R 33 Is preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group or an ethyl group, and still more preferably a methyl group.
  • R 21 ⁇ R 24 Is preferably a hydrogen atom or a monovalent aliphatic hydrocarbon group having 1 to 8 carbon atoms which may have a substituent, and more preferably a hydrogen atom or an ethyl group.
  • R 25 And R 26 Each independently represents a hydrogen atom or a methyl group. Of these, a hydrogen atom is preferable.
  • R 27 As an ethylene group and a propane-1,2-diyl group, an ethylene group is more preferable.
  • R 28 Is preferably a hydrogen atom.
  • n is an integer of 1 to 4, preferably an integer of 2 to 4, and more preferably 3 or 4.
  • 2- (2-hydroxyethoxy) ethyl group and 2- [2- (2-hydroxyethoxy) ethoxy] ethyl group are A 2- [2- (2-hydroxyethoxy) ethoxy] ethyl group is more preferable.
  • the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • preferred examples of the cation derived from the xanthene compound include cations represented by formulas (1-c1) to (1-c48).
  • Compound (A2) can be synthesized using a commercially available xanthene dye (for example, “Rhodamin 6G” manufactured by Taoka Chemical 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.
  • the colorant (A) (Ii) Instead of compound (A1) or together with compound (A1), (Iii) It contains at least one pigment selected from the group consisting of yellow pigments, orange pigments and red pigments.
  • yellow pigments include C.I. 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 and the like.
  • orange pigments include C.I. I.
  • 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 , 71, 73, and the like.
  • red pigments include C.I. 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.
  • C.I. I. Pigment yellow 138, 139, 150 C.I. I.
  • the colorant (A) may contain organic pigments other than yellow pigments, orange pigments and red pigments. Examples of such other pigments include C.I. I. And violet color pigments such as CI Pigment Violet 1 (hereinafter, CI Pigment Violet is omitted and only numbers are described), 19, 23, 29, 32, 36, and 38.
  • the pigment can be atomized by rosin treatment, surface treatment using a pigment derivative having an acidic group or basic group introduced, graft treatment on the pigment surface with a polymer compound, sulfuric acid atomization method, etc.
  • a treatment, a cleaning treatment with an organic solvent or water for removing impurities, a removal treatment with an ion exchange method of ionic impurities, or the like may be performed.
  • the pigment preferably has a uniform particle size.
  • the colored curable resin composition of the present invention contains a pigment as the colorant (A), it may contain a pigment dispersant.
  • 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 (Techno Co., Ltd.
  • Disperbyk Bic Chemie
  • the amount used is preferably 100 parts by mass, more preferably 5 parts by mass or more and 50 parts by mass or less, with respect to 100 parts by mass of 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 colorant (A) may contain both a dye different from the compound (A1) and the compound (A2).
  • the dye include oil-soluble dyes, acid dyes, amine salts of acid dyes, and sulfonamides of acid dyes, and are classified as dyes by, for example, the Color Index (published by The Society of Dyers 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.
  • the colored curable resin composition of the present invention may further contain a boron complex (F).
  • a boron complex (F) the anion represented by following formula (4) is mentioned, for example.
  • [W in Formula (4) 1 , W 2 Each independently represents a group formed by releasing protons from two monovalent proton-donating substituents.
  • Examples of the group formed by releasing two protons from the monovalent proton-donating substituent in the formula (4) include catechol which may have a substituent and 2,3-optionally substituted 2,3- Dihydroxynaphthalene, 2,2′-biphenol optionally having substituent, 3-hydroxy-2-naphthoic acid optionally having substituent, 2-hydroxy- optionally having substituent 1-naphthoic acid, 1-hydroxy-2-naphthoic acid optionally having substituent, binaphthol optionally having substituent, salicylic acid optionally having substituent, having substituent It is preferably benzyl acid which may be substituted or mandelic acid which 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-described substituent include, for example, Etc.
  • Examples of the mandelic acid optionally having 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-28), and formula (BC-25) to formula ( Anion (BC-25) to anion (BC-28) represented by 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 further contain a zinc complex (G).
  • a zinc complex (G) the zinc complex represented, for example by Formula (5) is mentioned.
  • 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. Among these, (5) -18 is preferable from the viewpoint of improving heat resistance.
  • the content of the zinc complex (G) is preferably 0.1 parts by mass or more and 30 parts by mass or less, and more preferably 0.5 parts by mass or more and 15 parts by mass or less with respect to 100 parts by mass of the colorant (A).
  • 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)”).
  • (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 Each independently represents 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 each independently 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 a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a 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 formula (I) include compounds represented by formula (I-1) to 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) in that the reliability of the resulting colored pattern, such as heat resistance and chemical resistance, can be further increased.
  • (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].
  • the resin [K1] is, for example, a method described in the document “Experimental Method for Polymer Synthesis” (Takayuki Otsu, published by Kagaku Dojin Co., Ltd., First Edition, First Edition, issued 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 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 within the following range among all the structural units constituting the resin [K2].
  • the ratio of the structural unit 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 described for the production method of resin [K1].
  • the resin [K4] is obtained by obtaining a copolymer of (b) and (c) and adding the carboxy group of (b) to the cyclic ether having 2 to 4 carbon atoms of (a). Can do.
  • a copolymer of (b) and (c) is produced in the same manner as the method described as the production method of [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.) 0.001 to 5 parts by mass with respect to 100 parts by mass of the total amount of (a) to (c), and a polymerization inhibitor (for example, hydroquinone etc.) etc. to a total amount of 100 parts by mass of (a) to (c).
  • the resin [K4] can be obtained by placing 0.001 to 5 parts by mass in a flask and reacting at 60 to 130 ° C. for 1 to 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 from 5 to 80 mol%, more preferably from 10 to 75 mol%, more preferably from 15 to 70 mol%, based on (b). 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
  • the resin [K1] and the resin [K2] are preferable, the 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, 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.
  • Examples thereof include 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one and 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutan-1-one. It is done.
  • 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.
  • 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 phenylsulfanyl acetic acid, methylphenylsulfanyl acetic acid, ethylphenylsulfanyl acetic acid, methylethylphenylsulfanyl acetic acid, dimethylphenylsulfanyl acetic acid, methoxyphenylsulfanyl acetic acid, dimethoxyphenylsulfanyl acetic acid, chlorophenylsulfanyl acetic acid, dichlorophenylsulfanyl acetic acid -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 polymerizable 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).
  • a solvent (E) is not specifically limited, The solvent normally used in the said field
  • ester solvents solvents containing —COO—
  • ether solvents other than ester solvents solvents containing —O—
  • ether ester solvents solvents containing —COO— and —O—
  • 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, diethyl Glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, methyl anisole, and the
  • 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 ether Acetate, propylene glycol monopropyl ether acetate,
  • 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 the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, glycerin and the like.
  • the aromatic hydrocarbon solvent 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. Among the above-mentioned solvents, an organic solvent having a boiling point at 1 atm of 120 ° C. or higher and 180 ° C. or lower is 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 surfactant examples include a surfactant having a siloxane bond.
  • fluorine-based surfactant include surfactants having a fluorocarbon chain.
  • Florard trade name
  • FC430 Fluorescence (trade name) FC430, FC431 (Sumitomo 3M Co., Ltd.), MegaFuck (trade name) F142D, F171, F172, F173, F177, F183, F183, R30, RS-718-K (manufactured by DIC Corporation), EFtop (trade name) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals), Surflon (tradename) S381, S382, SC101, SC105 (Asahi Glass Co., Ltd.), E5844 (Daikin Fine Chemical Laboratory Co., Ltd.) and the like.
  • 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 And a method using an inkjet apparatus that does not require a photolithographic 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, and the like. .
  • Examples of the application 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 the solvent removal / drying include natural drying, ventilation drying, vacuum 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.
  • the light source used for exposure is preferably a light source that generates light having a wavelength of 250 to 450 nm.
  • 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 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. Furthermore, you may post-bake as needed. 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, a coating film, a pattern, and a high-quality color filter having good heat resistance and light resistance can be obtained.
  • 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 weight average molecular weight (Mw) and the number average molecular weight (Mn) of the resin obtained in the synthesis example were measured using the GPC method under the following conditions. Apparatus; K2479 (manufactured by Shimadzu Corporation) Column; SHIMADZU Shim-pack GPC-80M Column temperature: 40 ° C Solvent; THF (tetrahydrofuran) Flow rate: 1.0 mL / min Detector; Standard material for RI calibration; TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)
  • the polystyrene-converted weight average molecular weight and number average molecular weight ratio (Mw / Mn) obtained above was defined as molecular weight distribution.
  • each component was mixed so that it might become a composition shown in Table 3, and the colored curable resin composition was obtained.
  • the pigment was mixed with a pigment dispersant and propylene glycol monomethyl ether acetate in the amount described in the column E-12 ) and dispersed in advance.
  • E-1 2) represents the total propylene glycol monomethyl ether acetate content.
  • each component represents the following.
  • resin (B) showed the mass part of solid content conversion.
  • Compound (A2) Compound represented by formula (1-c23)
  • Compound A1 Compound represented by formula (z-2)
  • Compound (A3) Pigment: C.I. I.
  • 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.
  • Light was irradiated with an exposure amount of 2 (based on 365 nm).
  • a photomask a mask on which a 100 ⁇ m line and space pattern was formed was used. After the 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.
  • a color filter excellent in brightness and contrast can be produced.

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Abstract

La présente invention concerne une composition de résine colorante durcissable contenant (A) un agent colorant, (B) une résine, (C) un composé photopolymérisable, (D) un agent d'amorçage de la photopolymérisation, et (E) un solvant, l'agent colorant (A) contenant au moins une substance sélectionnée dans le groupe constitué des substances suivantes (i), (ii) et (iii): (i) un composé répondant à la formule (A2), (ii) un composé répondant à la formule (A1), (iii) au moins un pigment sélectionné dans le groupe constitué de pigments jaunes, de pigments orange et de pigments rouges.
PCT/JP2014/065523 2013-06-07 2014-06-05 Composition de résine colorante durcissable WO2014196661A1 (fr)

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CN107057402A (zh) * 2017-06-15 2017-08-18 杭州荣彩实业有限公司 一种复合型颜料红rrr
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

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