WO2023037790A1 - 着色硬化性樹脂組成物、カラーフィルタ、表示装置、及び固体撮像素子 - Google Patents

着色硬化性樹脂組成物、カラーフィルタ、表示装置、及び固体撮像素子 Download PDF

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WO2023037790A1
WO2023037790A1 PCT/JP2022/029290 JP2022029290W WO2023037790A1 WO 2023037790 A1 WO2023037790 A1 WO 2023037790A1 JP 2022029290 W JP2022029290 W JP 2022029290W WO 2023037790 A1 WO2023037790 A1 WO 2023037790A1
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meth
acrylate
mass
group
structural unit
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PCT/JP2022/029290
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English (en)
French (fr)
Japanese (ja)
Inventor
真由子 松本
中山 萌黄 宮澤
勝治 井上
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住友化学株式会社
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Priority to KR1020247010525A priority Critical patent/KR20240054332A/ko
Priority to CN202280060427.3A priority patent/CN117916665A/zh
Publication of WO2023037790A1 publication Critical patent/WO2023037790A1/ja

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    • 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
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/04—Acids; Metal salts or ammonium salts thereof
    • C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1807—C7-(meth)acrylate, e.g. heptyl (meth)acrylate or benzyl (meth)acrylate
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • 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
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/14—Esterification
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • 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
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • 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
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
    • 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
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
    • H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
    • H01L27/144—Devices controlled by radiation
    • H01L27/146—Imager structures
    • H01L27/14601—Structural or functional details thereof
    • H01L27/1462—Coatings
    • H01L27/14621—Colour filter arrangements
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
    • H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
    • H01L27/144—Devices controlled by radiation
    • H01L27/146—Imager structures
    • H01L27/14643—Photodiode arrays; MOS imagers
    • H01L27/14645—Colour imagers

Definitions

  • the present invention relates to colored curable resin compositions, color filters, display devices, and solid-state imaging devices.
  • Color filters used in display devices such as liquid crystal display devices, electroluminescence display devices and plasma displays, and solid-state imaging devices such as CCD and CMOS sensors are produced from colored curable resin compositions.
  • a colored curable resin composition includes, as a resin, acrylic acid and 3,4-epoxytricyclo[5.2.1.0 2,6 ]decane-8 and/or 9-yl acrylate.
  • a colored curable resin composition containing a polymer is known (Patent Document 1).
  • an object of the present invention is to provide a colored curable resin composition capable of forming a color filter having excellent adhesion.
  • the gist of the present invention is as follows. [1] A colored curable resin composition containing a coloring agent, an alkali-soluble resin, a polymerizable compound, and a polymerization initiator, The colored curable resin composition, wherein the alkali-soluble resin contains an alkali-soluble resin containing a structural unit represented by formula (I).
  • R 1 represents a hydrogen atom or a methyl group.
  • R 2 represents an optionally substituted C 1-10 divalent aliphatic hydrocarbon group.
  • T 1 represents an optionally substituted C 6-20 divalent aromatic hydrocarbon group.
  • X represents -O-, -S- or -NR 3 -.
  • R 3 represents a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms.
  • T 2 represents an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms.
  • a display device including the color filter described in [2].
  • [4] A solid-state imaging device including the color filter according to [2].
  • the colored curable resin composition of the present invention includes a coloring agent (hereinafter sometimes referred to as a coloring agent (A)), an alkali-soluble resin (hereinafter sometimes referred to as an alkali-soluble resin (B)), a polymerizable compound (hereinafter sometimes referred to as , may be referred to as a polymerizable compound (C)), and a polymerization initiator (hereinafter, may be referred to as a polymerization initiator (D)).
  • the colored curable resin composition of the present invention may further contain a solvent (hereinafter sometimes referred to as solvent (E)).
  • the colored curable resin composition of the present invention may further contain a polymerization initiation aid (hereinafter sometimes referred to as polymerization initiation aid (D1)).
  • the colored curable resin composition of the present invention may further contain a thiol compound (hereinafter sometimes referred to as thiol compound (T)).
  • the colored curable resin composition of the present invention may further contain a leveling agent (hereinafter sometimes referred to as leveling agent (F)).
  • leveling agent hereinafter sometimes referred to as leveling agent (F)
  • coloring agent (A) examples include dyes (A1) and pigments (A2), with pigments (A2) being preferred. These may be used alone or in combination of two or more.
  • the dye (A1) is not particularly limited, and known dyes can be used, such as solvent dyes, acid dyes, direct dyes, and mordant dyes.
  • Dyes include, for example, compounds classified as dyes in the Color Index (published by The Society of Dyers and Colorists) and known dyes described in Dye Note (Shikisensha).
  • azo dyes cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinolines Dyes, nitro dyes, phthalocyanine dyes, perylene dyes, quinophthalone dyes, isoindoline dyes and the like.
  • organic solvent-soluble dyes are preferred.
  • C.I. Color Index
  • C.I. Color Index
  • Solvent Orange 2 7, 11, 15, 26, 41, 54, 56, 77, 86, 99; C. I. solvent violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; C. I. solvent blue 4, 5, 14, 18, 35, 36, 37, 38, 44, 45, 58, 59, 59: 1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; C. I. Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35; I. solvent dyes, C. I.
  • Basic Green 1 I. basic dye, C. I. Reactive Yellow 2, 76, 116; C. I. Reactive Orange 16; C. I. C.I. Reactive Red 36; I. reactive dyes, C. I. Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; C. I. Modern Tread 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38 , 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95; C. I.
  • These dyes may be appropriately selected according to the desired spectral spectrum of the color filter.
  • pigments classified as pigments in the Color Index can be used, for example, pigments classified as pigments in the Color Index (published by The Society of Dyers and Colorists). According to the chemical structure, azo pigments, cyanine pigments, triphenylmethane pigments, xanthene pigments, diketopyrrolopyrrole pigments, anthraquinone pigments, dioxazine pigments, naphthoquinone pigments, quinoneimine pigments, methine pigments, azomethine pigments, squarylium pigments, acridine pigments, styryl pigments, coumarin pigments, quinoline pigments, nitro pigments, phthalocyanine pigments, perylene pigments, quinophthalone pigments, isoindoline pigments, etc.
  • azo-based pigments diketopyrrolopyrrole-based pigments, dioxane-based pigments, azomethine-based pigments, phthalocyanine-based pigments, quinophthalone-based pigments, isoindoline-based pigments, and the like are preferred.
  • Pigments classified as pigments include C.I. I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, yellow pigments such as 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, 231; C. I. Orange pigments such as Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73; C. I.
  • These pigments may be appropriately selected according to the spectral spectrum of the desired color filter.
  • the colorant (A) When preparing a green colored curable resin composition, the colorant (A) includes yellow dyes and yellow pigments (hereinafter collectively referred to as “yellow colorants”), green dyes and green pigments. (these may be collectively referred to as “green coloring agents” hereinafter), and more preferably contains a yellow pigment and/or a green pigment.
  • yellow dyes include dyes classified as yellow in hue among the above dyes
  • examples of yellow pigments include pigments classified as yellow in hue among the above pigments.
  • yellow pigments quinophthalone-based pigments, azomethine-based pigments (especially metal-containing azomethine-based pigments), and isoindoline-based pigments are preferred.
  • I. Pigment Yellow 129, 138, 139, 150 and 185 are more preferred, and C.I. I. Pigment Yellow 138, 139, 150 and 185 are more preferred.
  • green dyes include dyes classified as green in hue among the above dyes
  • examples of green pigments include pigments classified as green in hue among the above pigments.
  • phthalocyanine pigments are preferred, and at least one selected from the group consisting of halogenated copper phthalocyanine pigments and halogenated zinc phthalocyanine pigments is more preferred.
  • I. Pigment Green 7, 36, 58, 59 are more preferred.
  • the colorant (A) is, in 100% by mass of all colorants, a total of a yellow colorant and/or a green colorant, for example, 50% by mass or more, preferably It preferably contains 70% by mass or more, more preferably 90% by mass or more, and particularly preferably 100% by mass.
  • it is preferable to contain both a yellow coloring agent and a green coloring agent and when both a yellow coloring agent and a green coloring agent are contained, the content of the green coloring agent is 100% by mass in total of the yellow coloring agent and the green coloring agent.
  • Medium for example, 30% by mass or more and 95% by mass or less, preferably 50% by mass or more and 90% by mass or less, and more preferably 60% by mass or more and 85% by mass or less.
  • the colorant (A) When preparing a red colored curable resin composition, the colorant (A) includes a yellow colorant, a red dye and a red pigment (hereinafter collectively referred to as "red colorant"). It preferably contains at least one selected from the group, and more preferably contains a yellow pigment and/or a red pigment.
  • yellow colorant examples include the same examples as in the case of preparing a green colored curable resin composition, and preferred embodiments are also the same.
  • red dyes include dyes classified as red in hue among the above dyes
  • examples of red pigments include pigments classified as red in hue among the above pigments.
  • red pigments C.I. I. Pigment Red 149, 176, 177, 242, 254, 255, 264, 269, 291 are preferred.
  • red pigments azo pigments and diketopyrrolopyrrole pigments are preferred, and C.I. I. Pigment Red 176, 242, 254, 255, 264, 269 and 291 are more preferred, and C.I. I. Pigment Red 242, 254, 269, 291 are more preferred.
  • the colorant (A) is a yellow colorant and/or a red colorant in total in 100% by mass of all colorants, for example, 50% by mass or more, preferably It preferably contains 70% by mass or more, more preferably 90% by mass or more, and particularly preferably 100% by mass. It also preferably contains both a yellow colorant and a red colorant.
  • the content of the red coloring agent is, for example, 30% by mass or more and 95% by mass or less in the total 100% by mass of the yellow coloring agent and the red coloring agent, and 50% by mass % or more and 90 mass % or less, and more preferably 60 mass % or more and 85 mass % or less.
  • the colorant (A) is selected from the group consisting of blue dyes and blue pigments (hereinafter collectively referred to as "blue colorants”). It preferably contains at least one type, and more preferably contains a blue pigment.
  • Blue dyes include dyes classified as blue in hue among the above dyes, and blue pigments include pigments classified as blue in hue among the above pigments.
  • a phthalocyanine pigment is preferable, and C.I. I. Pigment Blue 15, 15:3, 15:4, 15:6, 16 are more preferred.
  • violet colorant When preparing a blue colored curable resin composition, in addition to the blue colorant, violet color dye and violet color pigment (hereinafter collectively referred to as “violet colorant”) may also be contained. preferable.
  • Violet color dyes include dyes whose hue is classified as violet among the above dyes, and violet color pigments include pigments whose hue is classified as violet among the above pigments.
  • violet color pigments are preferred, and among violet color pigments, C.I. I. Pigment Violet 19, 23, 29 are more preferred.
  • the colorant (A) contains a blue colorant in an amount of, for example, 30% by mass or more and 99% by mass or less, preferably 50% by mass or more, based on 100% by mass of all colorants. , more preferably 60% by mass or more.
  • the content of the blue colorant is, for example, 30% by mass or more and 95% by mass or less, and 50% by mass or more in the total 100% by mass of the blue colorant and the violet colorant. 90% by mass or less is preferable, and 60% by mass or more and 85% by mass or less is more preferable.
  • the colorant (A) preferably contains at least one yellow colorant, more preferably contains at least one yellow pigment, and contains two or more yellow pigments. is more preferred.
  • yellow pigments quinophthalone-based pigments, azomethine-based pigments (especially metal-containing azomethine-based pigments), and isoindoline-based pigments are preferred, and C.I. I. Pigment Yellow 129, 138, 139, 150 and 185 are more preferred, and C.I. I. Pigment Yellow 138, 139, 150 and 185 are more preferred.
  • the colorant (A) is a yellow colorant in 100% by mass of the total colorant, for example, 50% by mass or more, preferably 70% by mass or more, more preferably It preferably contains 80% by mass or more, more preferably 90% by mass or more, and particularly preferably 100% by mass.
  • the colored curable resin composition contains the solvent (E)
  • the colored curable resin composition is prepared using the colorant-containing liquid.
  • a resin composition may be prepared.
  • the colorant (A) does not dissolve in the solvent (E)
  • the colorant-containing liquid contains the colorant (A) in the solvent (E). It can be prepared by dispersing and mixing.
  • the colorant-containing liquid may contain part or all of the solvent (E) contained in the colored curable resin composition.
  • the content of solids in the colorant-containing liquid is less than 100% by mass, preferably 0.01% by mass or more and 99.99% by mass or less, more preferably 0.99% by mass or less, with respect to the total amount of the colorant-containing liquid. 1% by mass or more and 99.9% by mass or less, more preferably 0.1% by mass or more and 99% by mass or less, even more preferably 0.5% by mass or more and 90% by mass or less, and particularly preferably 1% by mass or more and 50% by mass or less % by mass or less.
  • the content of the colorant (A) in the colorant-containing liquid is 100% by mass or less, preferably 0.001% by mass or more and 99.999% by mass, relative to the total amount of solids in the colorant-containing liquid. or less, more preferably 0.01% by mass or more and 99% by mass or less, still more preferably 0.1% by mass or more and 95% by mass or less, and even more preferably 0.5% by mass or more and 90% by mass or less and particularly preferably 1.0% by mass or more and 80% by mass or less.
  • the coloring agent (A) may optionally be subjected to rosin treatment, surface treatment using a derivative having an acidic or basic group introduced therein, grafting treatment to the surface of the coloring agent (A) with a polymer compound or the like, sulfuric acid It may be subjected to atomization treatment by an atomization method, salt milling method or the like, washing treatment with an organic solvent or water for removing impurities, removal treatment of ionic impurities by an ion exchange method or the like, and the like. It is preferable that the particle size of the colorant (A) is substantially uniform.
  • the coloring agent (A) can be uniformly dispersed in the solution by adding a dispersing agent and performing a dispersion treatment.
  • a dispersing agent When two or more types are used in combination as the colorant (A), each of them may be subjected to dispersion treatment alone, or a plurality of types may be mixed and subjected to dispersion treatment.
  • Dispersants include, for example, surfactants, and may be cationic, anionic, nonionic or amphoteric surfactants. Specific examples include surfactants such as polyester-based, polyamine-based and acrylic-based surfactants. These 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 registered trademark
  • EFKA registered trademark
  • the amount of the dispersant (solid content) to be used is usually 1 part by mass or more and 10000 parts by mass or less, preferably 100 parts by mass or less per 100 parts by mass of the colorant (A) in the colorant-containing liquid. It is 5 parts by mass or more and 5000 parts by mass or less, more preferably 10 parts by mass or more and 1000 parts by mass or less, and still more preferably 15 parts by mass or more and 800 parts by mass or less.
  • the amount of the dispersant used is within the above range, there is a tendency to obtain a colorant-containing liquid in a more uniformly dispersed state (hereinafter sometimes referred to as a colorant dispersion or a pigment dispersion).
  • a colored curable resin composition is prepared by using a colored curable resin composition after preparing a colored liquid containing a colored agent (A) and a solvent (E) in advance
  • the colored A part or all, preferably a part, of the alkali-soluble resin (B) contained in the curable resin composition may be included in advance.
  • the dispersion stability of the colorant-containing liquid can be further improved.
  • the content of the alkali-soluble resin (B) is, for example, 0.01 with respect to 100 parts by mass of the colorant (A) in the colorant-containing liquid. It is 10000 parts by mass or less, preferably 0.1 part by mass or more and 5000 parts by mass or less, more preferably 1 part by mass or more and 1000 parts by mass or less, and even more preferably 5 parts by mass or more and 500 parts by mass or less.
  • the content of the coloring agent (A) is preferably 1% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 70% by mass or less, based on the total solid content of the colored curable resin composition, It is more preferably 20% by mass or more and 65% by mass or less, and even more preferably 30% by mass or more and 60% by mass or less.
  • the content of the coloring agent (A) is within the above range, the color density of the resulting color filter is sufficient, and the required amount of the alkali-soluble resin (B) can be contained in the composition. It is preferable because a pattern with sufficient mechanical strength can be formed.
  • total amount of solid content in this specification refers to the amount obtained by subtracting the content of the solvent from the total amount of the colored curable resin composition.
  • the total amount of solids and the content of each component relative thereto can be measured by known analytical means such as liquid chromatography or gas chromatography.
  • Alkali-soluble resin (B) contains an alkali-soluble resin (Bi) containing a structural unit represented by formula (I) (hereinafter sometimes referred to as structural unit (I)).
  • Alkali solubility refers to the property of dissolving in a developer that is an aqueous solution of an alkaline compound.
  • the colored curable resin composition of the present invention can improve the adhesion of the formed color filter by containing an alkali-soluble resin having a specific structure. Moreover, according to the colored curable resin composition of the present invention, it is possible to reduce the generation of residues during development, preferably in the production of color filters.
  • Alkali-soluble resin (Bi) is a resin having structural unit (I).
  • R 1 represents a hydrogen atom or a methyl group.
  • R 2 represents an optionally substituted C 1-10 divalent aliphatic hydrocarbon group.
  • T 1 represents an optionally substituted C 6-20 divalent aromatic hydrocarbon group.
  • X represents -O-, -S- or -NR 3 -.
  • R 3 represents a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms.
  • T 2 represents an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms.
  • the divalent aliphatic hydrocarbon group having 1 to 10 carbon atoms represented by R 2 includes a divalent chain hydrocarbon group and a divalent alicyclic hydrocarbon group.
  • the divalent chain hydrocarbon group represented by R 2 may be saturated or unsaturated, but is preferably a divalent saturated chain hydrocarbon group.
  • Divalent saturated chain hydrocarbon groups include methylene group, ethylene group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6 -saturated linear hydrocarbon groups such as a diyl group, a heptane-1,7-diyl group, an octane-1,8-diyl group, a nonane-1,9-diyl group, and a decane-1,10-diyl group; and ethane-1,1-diyl group, propane-1,1-diyl group, propane-1,2-diyl group, propane-2,2-diyl group, butane-1,1-diyl group, butane-1,3 -diyl group, but
  • the divalent alicyclic hydrocarbon group represented by R 2 may be saturated or unsaturated, but is preferably a divalent saturated alicyclic hydrocarbon group.
  • the divalent saturated alicyclic hydrocarbon group includes a cyclopropane-1,2-diyl group, a cyclobutane-1,3-diyl group, a cyclopentane-1,3-diyl group, and a cyclohexane-1,4-diyl group.
  • monocyclic saturated alicyclic hydrocarbon groups such as cyclooctane-1,5-diyl group; and norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl and polycyclic saturated alicyclic hydrocarbon groups such as adamantane-2,6-diyl group.
  • the number of carbon atoms in the divalent alicyclic hydrocarbon group is preferably 3-10, more preferably 3-8, even more preferably 3-5.
  • the divalent aliphatic hydrocarbon group represented by R 2 is a combination of two or more divalent chain hydrocarbon groups and divalent alicyclic hydrocarbon groups, as long as the upper limit of the number of carbon atoms is 10. may be a group.
  • Such groups include, for example, -divalent chain hydrocarbon group-divalent alicyclic hydrocarbon group-, -divalent chain hydrocarbon group-bivalent alicyclic hydrocarbon group-2 valent chain hydrocarbon group - and the like.
  • the carbon number of the divalent chain hydrocarbon group and the group obtained by combining two or more divalent alicyclic hydrocarbon groups is preferably 4-10, more preferably 6-10.
  • the divalent aromatic hydrocarbon group represented by T 1 is a group in which two hydrogen atoms directly bonded to carbon atoms constituting the ring are replaced with bonds in an aromatic hydrocarbon ring.
  • the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group may be either a monocyclic ring or a condensed ring, such as benzene ring, naphthalene ring, anthracene ring, cyclobutadibenzene ring, phenanthrene ring, and Structures in which at least one hydrogen atom of an aromatic hydrocarbon ring is replaced with a hydrocarbon group, and the like.
  • hydrocarbon group examples include the groups exemplified as the hydrocarbon group having 1 to 6 carbon atoms represented by R 3 described later, preferably a saturated chain hydrocarbon group or an aromatic hydrocarbon group. , a saturated chain hydrocarbon group having 1 to 3 carbon atoms, or a phenyl group.
  • the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group is preferably a monocyclic ring, more preferably a monocyclic ring having a structure in which the hydrogen atoms of the aromatic hydrocarbon ring are not replaced by hydrocarbon groups.
  • the number of carbon atoms in the divalent aromatic hydrocarbon group is preferably 6-18, more preferably 6-14, even more preferably 6-10.
  • Specific examples of the divalent aromatic hydrocarbon group include groups represented by the following formulas (Ta-1) to (Ta-8). In the formula, * represents a bond.
  • the hydrocarbon group having 1 to 6 carbon atoms represented by R 3 includes an aliphatic hydrocarbon group and an aromatic hydrocarbon group.
  • Aliphatic hydrocarbon groups may be saturated or unsaturated and may be linear or alicyclic.
  • Saturated or unsaturated chain hydrocarbon groups represented by R 3 include linear alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group and hexyl group; isopropyl group, (1-ethyl ) propyl group, isobutyl group, sec-butyl group, tert-butyl group, (1-methyl)butyl group, (1-ethyl)butyl group, (2-ethyl)butyl group, isopentyl group, neopentyl group, tert-pentyl branched alkyl groups such as group, (2-methyl)pentyl group, isohexyl group; vinyl group, 1-propenyl group, 2-propenyl group (allyl group), (1-methyl)ethenyl group, 2-butenyl group, 3 -butenyl group, 1,3-butadienyl group, (1-(2-propenyl)
  • Saturated or unsaturated alicyclic hydrocarbon groups represented by R 3 include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl; cyclohexenyl (eg cyclohex-2-ene, cyclohexa- cycloalkenyl groups such as 3-ene); and the like.
  • the saturated or unsaturated alicyclic hydrocarbon group preferably has 3 to 6 carbon atoms.
  • the aromatic hydrocarbon group represented by R 3 includes a phenyl group.
  • the hydrocarbon group represented by R 3 may be a combination of two or more chain hydrocarbon groups and alicyclic hydrocarbon groups.
  • groups include, for example, 1-methylcyclopropyl group, 2-methylcyclopentyl group, alicyclic hydrocarbon group bonded with one or more alkyl groups such as 3-methylcyclopentyl group; cyclopropylmethyl group, cyclopropyl alkyl group to which one or more alicyclic hydrocarbon groups such as ethyl group, cyclobutylmethyl group, cyclobutylethyl group, cyclopentylmethyl group are bonded, 2-methylcyclopropylmethyl group, 2-methylcyclobutylmethyl group, 3 - an alkyl group to which an alicyclic hydrocarbon group to which one or more alkyl groups such as a methylcyclobutylmethyl group are bonded;
  • R 3 — represented by X specifically includes groups represented by the following formulas (Na-1) to (Na-9). In the formula, * represents a bond.
  • Aromatic hydrocarbon groups include, for example, aryl groups such as phenyl, 1-naphthyl, 2-naphthyl and biphenyl; o-tolyl, m-tolyl, p-tolyl and 2-ethylphenyl , 3-ethylphenyl group, 4-ethylphenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethyl phenyl group, 3,5-dimethylphenyl group, 2-methyl-6-ethylphenyl group, 2,6-diethylphenyl group, o-isopropylphenyl group
  • Substituents that each group represented by R 2 , T 1 and T 2 may have include a halogen atom, a nitro group, a cyano group, —OR a1 , —CO 2 R a1 , —SR a1 , — SO 2 R a1 , —SO 3 R a1 , —SO 3 M, —SO 2 NR a1 R a2 and —NR a1 R a2 and the like.
  • R a1 and R a2 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms
  • M represents a hydrogen atom or an alkali metal atom.
  • Examples of the hydrocarbon group having 1 to 6 carbon atoms represented by R a1 and R a2 include the groups exemplified as the hydrocarbon group having 1 to 6 carbon atoms represented by R 3 above.
  • the halogen atom includes a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • Examples of the alkali metal atom include sodium and potassium.
  • R a1 in —OR a1 is preferably a hydrogen atom, a saturated chain hydrocarbon group, or an aromatic hydrocarbon group, more preferably a hydrogen atom, a saturated chain hydrocarbon group having 1 to 3 carbon atoms, or an aromatic hydrocarbon group.
  • a hydrogen atom and a phenyl group are more preferred.
  • the divalent aliphatic hydrocarbon group represented by R 2 is preferably a divalent saturated chain hydrocarbon group, more preferably a divalent saturated chain hydrocarbon group having 1 to 8 carbon atoms. , more preferably a divalent saturated chain hydrocarbon group having 1 to 5 carbon atoms, more preferably a divalent saturated chain hydrocarbon group having 1 to 3 carbon atoms, and particularly preferably a methylene group.
  • the divalent aliphatic hydrocarbon group represented by R 2 may have a substituent, but preferably has no substituent.
  • the divalent aromatic hydrocarbon group represented by T 1 is preferably a group represented by the above formulas (Ta-1) to (Ta-8), and the groups represented by formulas (Ta-1) to (Ta- 3), groups represented by formulas (Ta-6) to (Ta-8) are more preferred, groups represented by formulas (Ta-1) to (Ta-3) are more preferred, and formula (Ta -2) and a group represented by the formula (Ta-3) are more preferred.
  • the divalent aliphatic hydrocarbon group represented by T 1 may have a substituent, but preferably has no substituent.
  • X is preferably -O-, -S-, or a group represented by the above formulas (Na-1) to (Na-9), and more preferably -O-.
  • the aromatic hydrocarbon group represented by T 2 is preferably an aryl group or an alkylaryl group, more preferably a phenyl group or a phenyl group to which an alkyl group having 1 to 6 carbon atoms is bonded, a phenyl group or a phenyl group having 1 to 6 carbon atoms.
  • a phenyl group to which 3 alkyl groups are bonded is more preferable, and a phenyl group, an o-tolyl group, an m-tolyl group and a p-tolyl group are even more preferable.
  • the number of substituents possessed by the aromatic hydrocarbon group represented by T 2 is preferably 0-3, more preferably 0-2, even more preferably 0-1.
  • structural units (I) include structural units (I-1) to (I-1) to which the combination of R 1 , R 2 , T 1 , T 2 and X is any one of Tables 1 to 6 below.
  • Structural unit (I-180) can be mentioned.
  • H is a hydrogen atom
  • Ta-1 to Ta-3 are groups represented by the above formulas (Ta-1) to (Ta-3)
  • Na-1 is the above formula (Na-1 )
  • La-1 to La10 mean groups represented by the following formulas (La-1) to (La-10).
  • structural unit (I) is preferably structural unit (I-1) to structural unit (I-60), more preferably structural unit (I-21) to structural unit (I-60), and structural unit ( I-21) to structural unit (I-40) are more preferred.
  • Structural unit (I) can be derived, for example, from a monomer represented by formula (Ii) below (hereinafter sometimes referred to as monomer "(Ii)").
  • R 1 , R 2 , X, T 1 and T 2 in the monomer represented by formula (Ii) are the same as those in structural unit (I).
  • alkali-soluble resin (Bi) examples include resins [Ki1] to [Ki8] having structural units shown in Table 7 below as essential units.
  • structural unit (I) and structural units (a) to (e) respectively mean the following structural units.
  • Structural unit (I) Same as structural unit (I) above Structural unit (a): At least one monomer selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter “monomer structural unit (b): a monomer having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter referred to as "monomer (b) Structural unit derived from structural unit (c): monomer (a) and copolymerizable monomer (however, monomer (a), monomer (b) and structural unit Structural unit derived from (hereinafter sometimes referred to as “monomer (c)”) (different from the monomer that induces (I)) Structural unit (d1): Structural unit (a) and monomer (b ) Structural unit (d2): Structural unit obtained by adding the monomer (a) to the structural unit (b
  • the total amount of essential structural units in the resins [Ki1] to [Ki8] shown in Table 7 is, for example, 80% by mass or more, preferably 90% by mass or more, more preferably 100% by mass, out of 100% by mass of all structural units. % by mass.
  • the monomer (a) 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-vinyl phthalic acid, 4-vinyl phthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyl Unsaturated dicarboxylic acids such as tetrahydrophthalic acid and 1,4-cyclohexenedicarboxylic 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-e, 5-
  • the monomer (b) is, for example, a cyclic ether structure having 2 to 4 carbon atoms (eg, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring) and an ethylenically unsaturated bond. compound.
  • Monomer (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.
  • the monomer (b) for example, a monomer having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “monomer (b1)”), an oxetanyl group and an ethylenically unsaturated bond, (hereinafter sometimes referred to as “monomer (b2)”), a monomer having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “monomer (b3)” ) and the like.
  • the monomer (b1) for example, a monomer having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as “monomer (b1-1)” some), and a monomer having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as “monomer (b1-2)”).
  • Examples of the monomer (b1-1) include glycidyl (meth)acrylate, ⁇ -methylglycidyl (meth)acrylate, ⁇ -ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether and m-vinylbenzyl glycidyl.
  • Examples of the monomer (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (eg, Celoxide 2000; manufactured by Daicel Corporation), and 3,4-epoxycyclohexylmethyl (meth)acrylate.
  • vinylcyclohexene monoxide 1,2-epoxy-4-vinylcyclohexane
  • Celoxide 2000 manufactured by Daicel Corporation
  • 3,4-epoxycyclohexylmethyl (meth)acrylate for example, Cychromer A400; manufactured by Daicel Corporation
  • Cychromer M100 for example, Cychromer M100; manufactured by Daicel Corporation
  • the compound represented by the formula (BI) and the formula Compounds represented by (BII) and the like can be mentioned.
  • R e and R f represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group is substituted with a hydroxy group.
  • X e and X f represent a single bond, *-R g -, *-R g -O-, *-R g -S- or *-R g -NH-.
  • R g represents an alkanediyl group having 1 to 6 carbon atoms. * represents a bond with O.
  • alkyl groups 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.
  • Alkyl groups in which hydrogen atoms are substituted with hydroxy include hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 1-hydroxy -1-methylethyl group, 2-hydroxy-1-methylethyl group, 1-hydroxybutyl group, 2-hydroxybutyl group, 3-hydroxybutyl group, 4-hydroxybutyl group and the like.
  • R e and R f are preferably a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group and a 2-hydroxyethyl group, more preferably a hydrogen atom and a methyl group.
  • alkanediyl groups include methylene, ethylene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane- A 1,6-diyl group and the like can be mentioned.
  • X e and X f are preferably a single bond, a methylene group, an ethylene group, *--CH 2 --O-- and *--CH 2 CH 2 --O--, more preferably a single bond and *--CH 2 CH 2 --O-- (* represents a bond with O).
  • Examples of the compound represented by formula (BI) include compounds represented by any one of formulas (BI-1) to (BI-15). Among them, formula (BI-1), formula (BI-3), formula (BII-5), formula (BI-7), formula (BI-9) or formula (BI-11) to formula (BI-15) A compound represented by is preferable, and a compound represented by formula (BI-1), formula (BI-7), formula (BI-9) or formula (BI-15) is more preferable.
  • Examples of the compound represented by formula (BII) include compounds represented by any one of formulas (BII-1) to (BII-15). Among them, formula (BII-1), formula (BII-3), formula (BII-5), formula (BII-7), formula (BII-9) or formula (BII-11) to formula (BII-15) A compound represented by is preferable, and a compound represented by formula (BII-1), formula (BII-7), formula (BII-9) or formula (BII-15) is more preferable.
  • the compound represented by formula (BI) and the compound represented by formula (BII) may be used alone or in combination of two or more.
  • the content ratio of these is On a molar basis, it is preferably 5:95 to 95:5, more preferably 10:90 to 90:10, still more preferably 20:80 to 80:20.
  • a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferable as the monomer (b2).
  • Examples of the monomer (b2) include 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3-acryloyl Oxymethyloxetane, 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3-methacryloyloxyethyloxetane, 3-ethyl-3-acryloyloxyethyloxetane and the like. be done.
  • a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferable as the monomer (b3).
  • Specific examples of the monomer (b3) include tetrahydrofurfuryl acrylate (eg, Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like.
  • the monomer (b) is preferably the monomer (b1) from the viewpoint of reducing residues during development in the production of color filters.
  • Examples of the monomer (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.
  • the structural unit (d1) of the structural unit (d) is a structural unit obtained by adding the monomer (b) to the structural unit (a), and the structural unit (a) that is the base of the structural unit (d1).
  • Preferred are structural units derived from unsaturated monocarboxylic acids such as acrylic acid and methacrylic acid.
  • a cyclic ether is highly reactive, and unreacted monomer (b) is less likely to remain.
  • a monomer (b1) having a bond is preferable, and a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized is more preferable, and glycidyl (meta) Acrylates are more preferred.
  • the structural unit (d2) includes a structural unit obtained by adding the monomer (a) to the structural unit (b) and does not overlap with the structural unit (d1).
  • the structural unit (d) preferably includes the following structural units.
  • Structural unit (e) is a structural unit obtained by adding a polyvalent carboxylic acid and/or carboxylic acid anhydride to the structural unit (d), more precisely, a hydroxy group and a polyvalent It is a structural unit in which a carboxylic acid and/or a carboxylic acid anhydride are ester-bonded.
  • Polyvalent carboxylic acids include oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, glutaric acid, tricarbanilic acid and the like.
  • Carboxylic anhydrides include succinic anhydride, maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinyl phthalic anhydride, 4-vinyl phthalic anhydride, and 3,4,5,6-tetrahydrophthalic acid. anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride and the like. Among these examples, those having no ethylenic double bond are preferred as polyvalent carboxylic acids and carboxylic acid anhydrides.
  • the structural unit (e) preferably includes the following structural units.
  • the ratio of each structural unit having as an essential unit is: Structural unit (I); 40 to 98 mol% Structural unit (a); 2 to 60 mol% is preferably Structural unit (I); 45 to 90 mol% Structural unit (a); 10 to 55 mol% is more preferable.
  • the resin [Ki1] is, for example, the method described in the document "Experimental Methods for Polymer Synthesis” (written by Takayuki Otsu, Published by Kagaku Dojin, 1st Edition, 1st Edition, March 1, 1972) and the document It can be manufactured with reference to the cited document described in .
  • predetermined amounts of monomer (Ii) and monomer (a), a polymerization initiator, a solvent, and the like are placed in a reaction vessel, and, for example, by replacing oxygen with nitrogen, a deoxygenated atmosphere is obtained. and heating and keeping warm while stirring.
  • the polymerization initiator, solvent, and the like used here are not particularly limited, and those commonly used in the relevant field can be used.
  • polymerization initiators include azo compounds (2,2′-azobisisobutyronitrile, 2,2′-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, t -Butyl peroxy-2-ethylhexanoate, etc.), and the solvent may be one that dissolves each monomer, and the solvent (E) of the colored curable resin composition of the present invention is described later. and the like.
  • the obtained copolymer may be used as a solution after the reaction as it is, may be used as a concentrated or diluted solution, or may be taken out as a solid (powder) by a method such as reprecipitation. You can use things.
  • the solvent contained in the colored curable resin composition of the present invention as a solvent in this polymerization, the solution after the reaction can be used as it is for the preparation of the colored curable resin composition of the present invention. Therefore, the manufacturing process of the colored curable resin composition of the present invention can be simplified.
  • the ratio of each structural unit having as an essential unit is Structural unit (I); 2 to 85 mol% Structural unit (a); 2 to 55 mol% Structural unit (b); 2 to 85 mol% is preferably Structural unit (I); 5 to 75 mol% Structural unit (a); 5 to 50 mol% Structural unit (b); 5 to 60 mol% is more preferable.
  • the ratio of the structural units of the resin [Ki2] is within the above range, the residue during development in the production of color filters can be further reduced, and preferably, the storage stability of the colored curable resin composition and the colored pattern can be improved. Excellent developability during formation and excellent solvent resistance of the resulting color filter.
  • the resin [Ki2] can be produced, for example, by the method described as the method for producing the resin [Ki1].
  • the ratio of each structural unit having as an essential unit is Structural unit (I); 2 to 85 mol% Structural unit (a); 2 to 55 mol% Structural unit (b); 2 to 85 mol% Structural unit (c); 1 to 50 mol% is preferably Structural unit (I); 5 to 75 mol% Structural unit (a); 5 to 50 mol% Structural unit (b); 5 to 60 mol% Structural unit (c); 2 to 40 mol% is more preferable.
  • the ratio of the structural units of the resin [Ki3] is within the above range, the residue during development in the production of color filters can be further reduced, and preferably, the storage stability of the colored curable resin composition and the colored pattern can be improved. Excellent developability during formation and excellent solvent resistance of the resulting color filter.
  • the resin [Ki3] can be produced, for example, in the same manner as the method for producing the resin [Ki1].
  • the ratio of each structural unit having as an essential unit is: Structural unit (I); 2 to 85 mol% Structural unit (a); 2 to 55 mol% Structural unit (c); 1 to 50 mol% is preferably Structural unit (I); 5 to 75 mol% Structural unit (a); 5 to 50 mol% Structural unit (c); 2 to 40 mol% is more preferable.
  • Resin [Ki4] can be produced, for example, in the same manner as described as the method for producing resin [Ki1].
  • the ratio of each structural unit having as an essential unit is Structural unit (I); 1 to 55 mol% Structural unit (a); 1 to 55 mol% Structural unit (d); 1 to 95 mol% is preferably Structural unit (I); 2 to 50 mol% Structural unit (a); 2 to 50 mol% Structural unit (d); 2 to 90 mol% is more preferable.
  • the resin [Ki5] is obtained by obtaining a copolymer of the monomer (Ii) and the monomer (a), and obtaining the carboxylic acid and/or carboxylic anhydride of the structural unit (a) in the copolymer.
  • a part of the monomer (b) is added with a cyclic ether having 2 to 4 carbon atoms, or the monomer (Ii) and the monomer (a) and the monomer (b)
  • the copolymer of the monomer (Ii) and the monomer (a), and the copolymer of the monomer (Ii), the monomer (a) and the monomer (b) are resins It can be produced by the same method as described as the production method of [Ki1].
  • the ratio of structural units derived from each monomer is Structural unit (I); 1 to 55 mol% Structural unit (a); 45 to 99 mol% is preferably Structural unit (I); 2 to 50 mol% Structural unit (a); 50 to 98 mol% is more preferable.
  • the ratio of the structural units derived from each monomer constitutes the copolymer Among all structural units, Structural unit (I); 1 to 55 mol% Structural unit (a); 1 to 55 mol% Structural unit (b); 1 to 95 mol% is preferably Structural unit (I); 2 to 50 mol% Structural unit (a); 2 to 50 mol% Structural unit (b); 2 to 90 mol% is more preferable.
  • the carbon of the monomer (b) is part of the carboxylic acid and/or carboxylic anhydride of the structural unit (a) in the copolymer of the monomer (Ii) and the monomer (a)
  • a reaction to add a cyclic ether having a number of 2 to 4, and a structural unit (b) in a copolymer of the monomer (Ii), the monomer (a) and the monomer (b) has 2 carbon atoms
  • the reaction of adding the carboxylic acid and/or carboxylic anhydride possessed by the monomer (a) to the cyclic ether of 1 to 4 includes a copolymer of the monomer (Ii) and the monomer (a), Alternatively, following the production of the copolymer of the monomer (Ii), the monomer (a) and the monomer (b), the atmosphere in the flask is replaced from nitrogen to air, and the monomer (b) or the monomer Polymer (a), a reaction catalyst (e.g., tris
  • the amount of the monomer (b) used in the reaction for adding the monomer (b) to the structural unit (a) is preferably 5 to 80 mol, more preferably 100 mol of the monomer (a). is 10-75 mol.
  • the amount of the monomer (a) used in the reaction for adding the monomer (a) to the structural unit (b) is preferably 5 to 100 mol per 100 mol of the monomer (b).
  • the amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass with respect to 100 parts by mass of the total amount of the monomers (a) and (b).
  • the amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of the monomers (a) and (b).
  • Reaction conditions such as the charging method, reaction temperature and time can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by polymerization, and the like.
  • 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 ratio of each structural unit having as an essential unit is Structural unit (I); 1 to 55 mol% Structural unit (a); 1 to 55 mol% Structural unit (c); 1 to 50 mol% Structural unit (d); 1 to 95 mol% is preferably Structural unit (I); 2 to 50 mol% Structural unit (a); 2 to 50 mol% Structural unit (c); 2 to 40 mol% Structural unit (d); 2 to 90 mol% is more preferable.
  • the resin [Ki6] can be produced, for example, by the method described as the method for producing the resin [Ki5].
  • the ratio of each structural unit having as an essential unit is Structural unit (I); 1 to 55 mol% Structural unit (d); 1 to 95 mol% Structural unit (e); 1 to 60 mol% is preferably Structural unit (I); 2 to 50 mol% Structural unit (d); 2 to 90 mol% Structural unit (e); 2 to 50 mol% is more preferable.
  • the ratio of the structural units of the resin [Ki7] is within the above range, it is possible to further reduce the residue during development in the production of color filters, and preferably, it is possible to reduce film loss in the exposed areas during development.
  • the resin [Ki7] is obtained by obtaining a copolymer of the monomer (Ii) and the monomer (a), and obtaining the carboxylic acid and/or carboxylic anhydride of the structural unit (a) in the copolymer.
  • a structural unit (d1) is formed by adding a cyclic ether having 2 to 4 carbon atoms possessed by the monomer (b), and a part of the hydroxy group possessed by the structural unit (d1) is a polycarboxylic acid and/or by adding a carboxylic acid anhydride.
  • the resin [Ki7] is obtained by obtaining a copolymer of the monomer (Ii) and the monomer (b), and obtaining a cyclic ether having 2 to 4 carbon atoms in the structural unit (b) in the copolymer. to form a structural unit (d2) by adding a carboxylic acid and/or a carboxylic anhydride possessed by the monomer (a), and a part of the hydroxy groups possessed by the structural unit (d2) is a polyvalent carboxylic acid It can also be produced by adding an acid and/or a carboxylic acid anhydride.
  • a copolymer of the monomer (Ii) and the monomer (a) and a copolymer of the monomer (Ii) and the monomer (b) are prepared as a method for producing the resin [Ki1]. It can be manufactured in a manner similar to that described.
  • the ratio of the structural units derived from each monomer is the monomer ( It is the same as the ratio in the copolymer of Ii) and the monomer (a), and is derived from each monomer in the copolymer of the monomer (Ii) and the monomer (b) Regarding the ratio of the structural units, the monomer (a) in the copolymer of the monomer (Ii) and the monomer (a) in the description of the production method of the resin [Ki5] is replaced with the monomer (b). It is the same as the ratio after reading.
  • the monomer (b) has 2 to 2 carbon atoms. 4, and a cyclic ether having 2 to 4 carbon atoms in the structural unit (b) in the copolymer of the monomer (Ii) and the monomer (b).
  • the reaction for adding the carboxylic acid and/or carboxylic anhydride of (a) the same addition reaction as described in the method for producing the resin [Ki5] can be mentioned.
  • the amount of the monomer (b) used in the reaction for adding the monomer (b) to the structural unit (a) is preferably 5 to 100 mol per 100 mol of the monomer (a).
  • the amount of the monomer (a) used in the reaction for adding the monomer (a) to the structural unit (b) is preferably 5 to 100 mol per 100 mol of the monomer (b).
  • the amount of the polyvalent carboxylic acid and/or carboxylic anhydride used in the reaction of adding the polyvalent carboxylic acid and/or carboxylic anhydride to the structural unit (d) in the copolymer is 100 of the structural unit (d). It is preferably 5 to 80 mol, more preferably 10 to 50 mol per mol.
  • the ratio of each structural unit having as an essential unit is Structural unit (I); 1 to 55 mol% Structural unit (c); 1 to 50 mol% Structural unit (d); 1 to 95 mol% Structural unit (e); 1 to 60 mol% is preferably Structural unit (I); 2 to 50 mol% Structural unit (c); 2 to 40 mol% Structural unit (d); 2 to 90 mol% Structural unit (e); 2 to 50 mol% is more preferable.
  • the ratio of the structural units of the resin [Ki8] is within the above range, it is possible to further reduce the residue during development in the production of color filters, and preferably, it is possible to reduce film loss in the exposed areas during development.
  • the resin [Ki8] can be produced, for example, by the method described as the production method of the resin [Ki7].
  • alkali-soluble resin (Bi) examples include phenoxybenzyl (meth)acrylate/(meth)acrylic acid copolymer, tolyloxybenzyl (meth)acrylate/(meth)acrylic acid copolymer, hydroxyphenoxybenzyl ( Resin [Ki1] such as meth)acrylate/(meth)acrylic acid copolymer, phenoxyphenoxybenzyl (meth)acrylate/(meth)acrylic acid copolymer; 3,4-epoxycyclohexylmethyl (meth)acrylate/(meth)acrylic acid/phenoxybenzyl (meth)acrylate copolymer, 3,4-epoxycyclohexylmethyl (meth)acrylate/(meth)acrylic acid/tolyloxybenzyl ( meth)acrylate copolymer, 3,4-epoxycyclohexylmethyl (meth)acrylate/(meth)acrylic acid/hydroxyphenoxybenzyl (meth)acryl
  • Hydroxyphenoxybenzyl (meth)acrylate/tricyclodecyl resin obtained by reacting succinic acid to resin obtained by adding glycidyl (meth)acrylate to acrylate/tricyclodecyl (meth)acrylate/(meth)acrylic acid copolymer (Meth)acrylate/(meth)acrylic acid copolymer to which glycidyl (meth)acrylate is added and succinic acid is further reacted, phenoxyphenoxybenzyl (meth)acrylate/tricyclodecyl (meth)acrylate/ Resin obtained by further reacting succinic acid to resin obtained by adding glycidyl (meth)acrylate to (meth)acrylic acid copolymer, phenoxybenzyl (meth)acrylate / tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate A copolymer of tolyloxybenzyl (meth)acrylate/tri
  • (Meth)acrylic acid-reacted resin, succinic acid-reacted resin, copolymer of hydroxyphenoxybenzyl (meth)acrylate/tricyclodecyl (meth)acrylate/glycidyl (meth)acrylate A resin obtained by reacting an acid-reacted resin with succinic acid, a copolymer of phenoxyphenoxybenzyl (meth)acrylate/tricyclodecyl (meth)acrylate/glycidyl (meth)acrylate and reacted with (meth)acrylic acid.
  • a resin obtained by reacting succinic acid with a resin obtained by reacting succinic acid and a resin obtained by reacting a copolymer of phenoxybenzyl (meth)acrylate/tricyclodecyl (meth)acrylate/styrene/glycidyl (meth)acrylate with (meth)acrylic acid.
  • the alkali-soluble resin (Bi) is preferably resin [Ki1], resin [Ki2], resin [Ki3], resin [Ki7], resin [Ki8], resin [Ki1], resin [Ki2], resin [ Ki7] is more preferred.
  • the polystyrene equivalent weight average molecular weight (Mw) of the alkali-soluble resin (Bi) is preferably 3,000 or more and 100,000 or less, more preferably 4,000 or more and 50,000 or less, and still more preferably 5,000 or less. 000 or more and 30,000 or less.
  • Mw polystyrene equivalent weight average molecular weight
  • the dispersion degree [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the alkali-soluble resin (Bi) is preferably 1.1 or more and 6 or less, more preferably 1.2 or more and 4 or less.
  • the acid value of the alkali-soluble resin (Bi) is preferably 10 mg-KOH/g or more and 300 mg-KOH/g or less, more preferably 20 mg-KOH/g or more and 250 mg-KOH/g or less, in terms of solid content. , More preferably 25 mg-KOH/g or more and 200 mg-KOH/g or less, still more preferably 30 mg-KOH/g or more and 150 mg-KOH/g or less, particularly preferably 30 mg-KOH/g or more and 130 mg-KOH / g or less.
  • the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the alkali-soluble resin (Bi), and can be obtained, for example, by titration using an aqueous potassium hydroxide solution. can be done.
  • the alkali-soluble resin (B) may contain an alkali-soluble resin that does not contain the structural unit (I) (hereinafter sometimes referred to as an alkali-soluble resin (Bii)).
  • Alkali-soluble resin (Bii) may be used alone or in combination of two or more.
  • alkali-soluble resin (Bii) examples include resins [K1] to [K7] having structural units shown in Table 8 below as essential units.
  • Structural units (a) to (e) in Table 8 have the same meanings as the structural units (a) to (e) described above, and preferred embodiments are also the same.
  • the total amount of the essential structural units in the resins [K1] to [K7] shown in Table 8 is, for example, 80% by mass or more, preferably 90% by mass or more, more preferably 100% by mass, out of 100% by mass of all structural units. % by mass.
  • the ratio of each structural unit having as an essential unit is Structural unit (a); 2 to 60 mol% Structural unit (b); 40 to 98 mol% is preferably Structural unit (a); 10 to 50 mol% Structural unit (b); 50 to 90 mol% is more preferable.
  • the resin [K1] can be produced, for example, in the same manner as the method for producing the resin [Ki1].
  • the ratio of each structural unit having as an essential unit is Structural unit (a); 2 to 45 mol% Structural unit (b); 2 to 95 mol% Structural unit (c); 1 to 65 mol% is preferably Structural unit (a); 5 to 40 mol% Structural unit (b); 5 to 80 mol% Structural unit (c); 5 to 60 mol% is more preferable.
  • the resin [K2] can be produced, for example, in the same manner as the method for producing the resin [Ki1].
  • the ratio of each structural unit having as an essential unit is: Structural unit (a); 2 to 60 mol% Structural unit (c); 40 to 98 mol% is preferably Structural unit (a); 10 to 50 mol% Structural unit (c); 50 to 90 mol% is more preferable.
  • Resin [K3] can be produced, for example, in the same manner as the method for producing resin [Ki1].
  • the ratio of each structural unit having as an essential unit is Structural unit (a); 5 to 90 mol% Structural unit (d); 10 to 95 mol% is preferably Structural unit (a); 10 to 80 mol% Structural unit (d); 20 to 90 mol% is more preferable.
  • Resin [K4] is obtained by obtaining a polymer from monomer (a), and adding monomer (b ) is added with a cyclic ether having 2 to 4 carbon atoms, or a copolymer of the monomer (a) and the monomer (b) is obtained, and the structural unit (b) in the copolymer can be produced by adding a carboxylic acid and/or a carboxylic acid anhydride possessed by the monomer (a) to a cyclic ether having 2 to 4 carbon atoms.
  • the ratio of the structural units derived from each monomer is preferably the same as the ratio mentioned for the resin [K1]. .
  • the formation reaction of the structural unit (d) can be carried out under the same conditions as the formation reaction of the structural unit (d) in the method for producing the resin [Ki5].
  • the ratio of each structural unit having as an essential unit is Structural unit (a); 1 to 55 mol% Structural unit (c); 1 to 50 mol% Structural unit (d); 1 to 95 mol% is preferably Structural unit (a); 2 to 50 mol% Structural unit (c); 2 to 40 mol% Structural unit (d); 2 to 90 mol% is more preferable.
  • the resin [K5] can be produced, for example, by the method described as the method for producing the resin [Ki5].
  • the ratio of each structural unit having as an essential unit is Structural unit (d); 5 to 98 mol% Structural unit (e); 2 to 95 mol% is preferably Structural unit (d); 8 to 95 mol% Structural unit (e); 5 to 92 mol% is more preferable.
  • the resin [K6] can be produced, for example, in the same manner as the method for producing the resin [Ki7].
  • the ratio of each structural unit having as an essential unit is: Structural unit (c); 1 to 50 mol% Structural unit (d); 1 to 95 mol% Structural unit (e); 1 to 60 mol% is preferably Structural unit (c); 2 to 40 mol% Structural unit (d); 2 to 90 mol% Structural unit (e); 2 to 50 mol% is more preferable.
  • the resin [K7] can be produced, for example, in the same manner as the method for producing the resin [Ki7].
  • alkali-soluble resin (Bii) examples include 3,4-epoxycyclohexylmethyl (meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2 ,6 ] resin [K1] such as decyl acrylate/(meth)acrylic acid copolymer; glycidyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer, glycidyl (meth)acrylate/styrene/ (Meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylate/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, 3,4-epoxy tricyclo[5.2.1.0 2,6 ]decyl acrylate/(meth)acrylic acid/N-cyclohexylmaleimide/2-
  • Resin [K6] such as reacted resin; resin obtained by further reacting tetrahydrophthalic anhydride with a resin obtained by adding glycidyl (meth)acrylate to benzyl (meth)acrylate/(meth)acrylic acid copolymer; Resin obtained by adding glycidyl (meth)acrylate to cyclodecyl (meth)acrylate/styrene/(meth)acrylic acid copolymer and further reacting it with tetrahydrophthalic anhydride, tricyclodecyl (meth)acrylate/benzyl (Meth)acrylic acid/tricyclodecyl (meth)acrylate resin obtained by further reacting tetrahydrophthalic anhydride with resin obtained by adding glycidyl (meth)acrylate to (meth)acrylate/(meth)acrylic acid copolymer / Resin obtained by reacting a copolymer of glycidyl (me
  • resin [K1] and resin [K2] are preferable, and resin [K2] is more preferable.
  • the polystyrene equivalent weight average molecular weight (Mw) of the alkali-soluble resin (Bii) is preferably 3,000 or more and 100,000 or less, more preferably 4,000 or more and 50,000 or less, and still more preferably 5, 000 or more and 30,000 or less.
  • Mw polystyrene equivalent weight average molecular weight
  • the weight-average molecular weight is within the above range, the unexposed area tends to have high solubility in a developer, and the resulting colored pattern tends to have a high residual film rate and hardness.
  • the dispersion degree [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the alkali-soluble resin (Bii) is preferably 1.1 or more and 6 or less, more preferably 1.2 or more and 4 or less.
  • the acid value of the alkali-soluble resin (Bii) is preferably 10 mg-KOH/g or more and 300 mg-KOH/g or less, more preferably 20 mg-KOH/g or more and 250 mg-KOH/g or less, in terms of solid content. , More preferably 25 mg-KOH/g or more and 200 mg-KOH/g or less, still more preferably 30 mg-KOH/g or more and 150 mg-KOH/g or less, particularly preferably 30 mg-KOH/g or more and 130 mg-KOH / g or less.
  • the content of the alkali-soluble resin (B) is preferably 5% by mass or more and 65% by mass or less, more preferably 10% by mass or more and 60% by mass or less, relative to the total solid content of the colored curable resin composition. , more preferably 15% by mass or more and 55% by mass or less, and even more preferably 18% by mass or more and 50% by mass or less.
  • a colored pattern can be formed, and the adhesion of the color filter is more excellent, and more preferably, the residue during development in the production of the color filter is further reduced. can.
  • the content of the alkali-soluble resin (Bi) may be 100% by mass, preferably 5% by mass or more and 99% by mass or less, more preferably 10% by mass in the total solid content of the alkali-soluble resin (B). % or more and 98 mass % or less, more preferably 15 mass % or more and 97 mass % or less, and even more preferably 20 mass % or more and 85 mass % or less.
  • the content of the alkali-soluble resin (Bi) is preferably 1 % by mass or more and 65% by mass or less, more preferably 1% by mass or more and 55% by mass or less, relative to the total amount of solids in the colored curable resin composition. , more preferably 2 to 45 mass %, still more preferably 2 to 40 mass %, and particularly preferably 3 to 35 mass %.
  • the content of the alkali-soluble resin (Bii) is preferably 1% by mass or more and 95% by mass or less in the total solid content of the alkali-soluble resin (B). , more preferably 5% by mass or more and 90% by mass or less, still more preferably 10% by mass or more and 80% by mass or less, and even more preferably 15% by mass or more and 70% by mass or less.
  • the polymerizable compound (C) is a compound that can be polymerized by an active radical and/or an acid generated from the polymerization initiator (D). is a (meth)acrylic acid ester compound.
  • polymerizable compounds having one ethylenically unsaturated bond examples include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, and N-vinylpyrrolidone. etc., and the monomers (a), (b) and (c) described above.
  • Polymerizable compounds having two ethylenically unsaturated bonds include, for example, 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, (meth)acrylate, bis(acryloyloxyethyl)ether of bisphenol A, 3-methylpentanediol di(meth)acrylate and the like.
  • the polymerizable compound (C) is preferably a polymerizable compound having 3 or more ethylenically unsaturated bonds.
  • examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa( meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tris(2-(meth)acryloyloxyethyl ) isocyanurate, ethylene glycol-modified pent
  • the weight average molecular weight of the polymerizable compound (C) is preferably 50 or more and 4,000 or less, more preferably 70 or more and 3,500 or less, still more preferably 100 or more and 3,000 or less, and still more preferably is 150 or more and 2,900 or less, and particularly preferably 250 or more and 1,500 or less.
  • the content of the polymerizable compound (C) may be, for example, 1% by mass or more and 99% by mass or less, preferably 5% by mass or more and 90% by mass or less, relative to the total solid content of the colored curable resin composition. , more preferably 8% by mass or more and 80% by mass or less, and still more preferably 10% by mass or more and 70% by mass or less.
  • the polymerization initiator (D) is not particularly limited as long as it is a compound capable of initiating polymerization by generating active radicals, acids, etc. by the action of light or heat, and known polymerization initiators can be used.
  • Examples of the polymerization initiator (D) include O-acyloxime compounds, alkylphenone compounds, biimidazole compounds, triazine compounds and acylphosphine oxide compounds.
  • the O-acyloxime compound is a compound having a partial structure represented by formula (d-1).
  • * represents a bond.
  • O-acyloxime compounds examples include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane, -1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6- (2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6- ⁇ 2-methyl-4-(3,3-dimethyl-2, 4-dioxacyclopentanylmethyloxy)benzoyl ⁇ -9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl
  • Irgacure OXE01 N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine
  • Irgacure OXE02 N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl) -9H-carbazol-3-yl]ethan-1-imine) (manufactured by BASF)
  • PBG-327 N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one- 2-imine; manufactured by Changzhou Strong Electronic New Materials Co., Ltd.
  • Adeka Arcles NCI-930 N-acetyloxy-1-(4-(4-(2-hydroxyethoxy)phenylsulfanyl)phenyl)propane-1- On-2-imine
  • Adeka Optomer N-1919 manufactured by ADEKA
  • O-acyloxime compounds include N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl ) butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2 -methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, and N- At least one selected from the group consisting of acetyloxy-1-(4-(4-(2-hydroxyethoxy)phenylsulfanyl)phenyl
  • the alkylphenone compound is a compound having a partial structure represented by formula (d-2) or a partial structure represented by formula (d-3).
  • the benzene ring may have a substituent.
  • * represents a bond.
  • Examples of compounds having a partial structure represented by formula (d-2) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1- (4-morpholinophenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butane-1 -on and the like.
  • Commercially available products such as Irgacure 369, 907 and 379 (manufactured by BASF) may also be used.
  • Examples of compounds having a partial structure represented by formula (d-3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4- (2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexylphenyl ketone, oligomer of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, ⁇ , ⁇ - diethoxyacetophenone, benzyl dimethyl ketal, and the like.
  • the alkylphenone compound is preferably a compound having a partial structure represented by formula (d-2).
  • triazine compound examples include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4- methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxy styryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4 -bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,
  • acylphosphine oxide compound examples include 2,4,6-trimethylbenzoyldiphenylphosphine oxide.
  • Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) may also be used.
  • biimidazole compound examples include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)- 4,4',5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372 and JP-A-6-75373), 2,2'-bis(2-chlorophenyl)-4, 4′,5,5′-tetraphenylbiimidazole, 2,2′-bis(2-chlorophenyl)-4,4′,5,5′-tetra(alkoxyphenyl)biimidazole, 2,2′-bis( 2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trial
  • the polymerization initiator (D) includes benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and 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 phenylglyoxylate, titanocene compounds and the like. These are preferably used in combination with a polymerization initiation aid (D1) (especially
  • Polymerization initiators that generate acids include, for example, 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetoxy Onium salts such as phenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, diphenyliodonium hexafluoroantimonate, and nitrobenzyl tosylate and benzoin tosylate.
  • a polymerization initiator containing at least one selected from the group consisting of alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds and biimidazole compounds is preferred, and O-acyloxy A polymerization initiator containing an amine compound or a biimidazole compound is more preferable, and a polymerization initiator containing an O-acyloxime compound is even more preferable.
  • the content of the polymerization initiator (D) is preferably 0.1 parts by mass or more and 30 parts by mass or less with respect to 100 parts by mass of the total amount of the alkali-soluble resin (B) and the polymerizable compound (C), and more Preferably, it is 1 part by mass or more and 20 parts by mass or less.
  • the content of the polymerization initiator (D) is within the above range, the sensitivity tends to be increased and the exposure time tends to be shortened, thereby improving the productivity of the optical filter.
  • the polymerization initiation aid (D1) is a compound or a sensitizer used to accelerate the polymerization of the polymerizable compound (C) whose polymerization has been initiated by the polymerization initiator (D).
  • the polymerization initiation aid (D1) is included, it is usually used in combination with the polymerization initiator (D).
  • Examples of the polymerization initiation aid (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-dimethylp-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone and 4,4'-bis( ethylmethylamino)benzophenone and the like, preferably 4,4'-bis(diethylamino)benzophenone.
  • EAB-F manufactured by Hodogaya Chemical Industry Co., Ltd.
  • Alkoxyanthracene compounds include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxy and anthracene and 2-ethyl-9,10-dibutoxyanthracene.
  • Thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone and 1-chloro-4-propoxythioxanthone.
  • 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 and naphthoxyacetic acid.
  • the content thereof is based on the total amount of 100 parts by mass of the total amount of the alkali-soluble resin (B) and the polymerizable compound (C) contained in the colored curable resin composition. , preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass.
  • the solvent (E) is not particularly limited, and solvents commonly used in the field can be used.
  • the solvent (E) is, for example, an ester solvent (a solvent containing -COO- in the molecule but not containing -O-), an ether solvent (a solvent containing -O- in the molecule but not containing -COO-), Ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- in the molecule but not containing -COO-), alcohol solvents (containing OH in the molecule , —O—, —CO— and —COO—-free solvents), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide and the like. These solvents may be used in combination of two or more.
  • Ester solvents include 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 and ⁇ -butyrolactone.
  • 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, and 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, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetol, methylanisole 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 ether acetate, propylene glycol monopropyl ether a
  • 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.
  • Alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol and glycerin.
  • Aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.
  • Amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidone.
  • propylene glycol monomethyl ether acetate propylene glycol monomethyl ether, ethyl lactate and cyclohexanone are preferred, and propylene glycol monomethyl ether acetate and propylene glycol monomethyl ether are more preferred.
  • the content of the solvent (E) is usually 99.99% by mass or less, preferably 40% by mass or more and 99% by mass or less, relative to the total amount of the colored curable resin composition. more preferably 50% by mass or more and 97% by mass or less, still more preferably 70% by mass or more and 96% by mass or less, and even more preferably 73% by mass or more and 95% by mass or less.
  • the total solid content of the colored curable resin composition is usually 0.01% by mass or more, preferably 1% by mass or more and 60% by mass or less, more preferably 3% by mass or more and 50% by mass or less.
  • a thiol compound (T) is a compound having a sulfanyl group (--SH) in its molecule.
  • Compounds having one sulfanyl group in the molecule include, for example, 2-sulfanyloxazole, 2-sulfanylthiazole, 2-sulfanylbenzimidazole, 2-sulfanylbenzothiazole, 2-sulfanylbenzoxazole, 2-sulfanylnicotinic acid, 2 -sulfanylpyridine, 2-sulfanylpyridin-3-ol, 2-sulfanylpyridine-N-oxide, 4-amino-6-hydroxy-2-sulfanylpyrimidine, 4-amino-6-hydroxy-2-sulfanylpyrimidine, 4- amino-2-sulfanylpyrimidine, 6-amino-5-nitroso-2-thiouracil, 4,5-diamino-6-hydroxy-2-sulfanylpyrimidine, 4,6-diamino-2-sulfanylpyrimidine, 2,4-diamino -6-sulfanylpyrimidine,
  • Compounds having two or more sulfanyl groups in the molecule include hexanedithiol, decanedithiol, 1,4-bis(methylsulfanyl)benzene, butanediolbis(3-sulfanylpropionate), butanediolbis(3-sulfanyl acetate), ethylene glycol bis(3-sulfanyl acetate), trimethylolpropane tris(3-sulfanyl acetate), butanediol bis(3-sulfanylpropionate), trimethylolpropane tris(3-sulfanylpropionate), tri methylolpropane tris (3-sulfanyl acetate), pentaerythritol tetrakis (3-sulfanyl propionate), pentaerythritol tetrakis (3-sulfanyl acetate), trishydroxyethyl tris
  • the content of the thiol compound (T) is preferably 0.5 to 50 parts by mass, more preferably 5 to 45 parts by mass, and still more preferably 10 to 40 parts by mass with respect to 100 parts by mass of the polymerization initiator (D). part by mass.
  • the content of the thiol compound (T) is within this range, the sensitivity tends to be high and the developability tends to be good.
  • Leveling agent (F) examples include silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants having fluorine atoms. These may have a polymerizable group in the side chain.
  • silicone-based surfactants include surfactants that have siloxane bonds in their molecules.
  • Toray Silicone DC3PA, Toray SH7PA, Toray DC11PA, Toray SH21PA, Toray SH28PA, Toray SH29PA, Toray SH30PA, Toray SH8400 (trade name: Dow Corning Toray Co., Ltd.), KP321, KP322, KP323, KP324 , KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (manufactured by Momentive Performance Materials Japan LLC), etc. .
  • fluorine-based surfactants include surfactants that have a fluorocarbon chain in the molecule.
  • Florard registered trademark
  • FC430 Florard FC431 (manufactured by Sumitomo 3M Co., Ltd.)
  • Megafac registered trademark
  • F142D Florado F171, Flora F172, Flora F173, Flora F177, Flora F183, Flora F554 R30, RS-718-K (manufactured by DIC Corporation), F-top (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, S382, SC101, SC105 (manufactured by AGC Co., Ltd.) and E5844 (manufactured by Daikin Fine Chemicals Laboratory Co., Ltd.).
  • silicone-based surfactants having fluorine atoms include surfactants having siloxane bonds and fluorocarbon chains in the molecule.
  • Megafac registered trademark
  • Megafac BL20 Megafac F475, F477 and F443 (manufactured by DIC Corporation) and the like can be mentioned.
  • the content of the leveling agent (F) is preferably 0.0005% by mass or more and 1% by mass or less, more preferably It is 0.001% by mass or more and 0.5% by mass or less, more preferably 0.005% by mass or more and 0.1% by mass or less. This content does not include the content of the pigment dispersant.
  • the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.
  • the colored curable resin composition may optionally contain additives known in the art such as fillers, other polymer compounds, adhesion promoters, quenchers, antioxidants, light stabilizers, chain transfer agents, etc. may include
  • the colored curable resin composition contains a coloring agent (A), an alkali-soluble resin (B), a polymerizable compound (C), a polymerization initiator (D), and an optional polymerization initiation aid (D1), It can be prepared by mixing a solvent (E), a thiol compound (T), a leveling agent (F) and other ingredients. Mixing can be performed by a known or commonly used device and conditions.
  • the colorant (A) is mixed in advance with part or all of the solvent (E), and then dispersed using a bead mill or the like until the average particle size becomes about 0.2 ⁇ m or less. It may be used, and is preferably used as a colorant-containing liquid.
  • the dispersant and the alkali-soluble resin (B) may be partly or wholly blended.
  • the desired colored curable resin composition can be prepared by mixing the colorant-containing liquid thus obtained with the remaining components so as to have a predetermined concentration.
  • the dye may be dissolved in advance in part or all of the solvent (E) to prepare a solution. It is preferable to filter the solution through a filter having a pore size of about 0.01 to 1 ⁇ m.
  • a color filter can be formed from the colored curable resin composition of the present invention.
  • methods for producing a colored pattern include a photolithography method, an inkjet method, a printing method, and the like.
  • the photolithographic method is preferred.
  • Photolithography is a method in which the colored curable resin composition is applied to a substrate, dried to form a colored composition layer, exposed through a photomask, and developed.
  • a colored coating film which is a cured product of the colored composition layer, can be formed by not using a photomask during exposure and/or not developing.
  • the colored pattern or colored coating film thus formed is the color filter of the present invention.
  • the film thickness of the color filter to be produced is not particularly limited, and can be appropriately adjusted according to the purpose and application. or less, preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more, further preferably 0.3 ⁇ m or more.
  • the substrate examples include glass plates such as quartz glass, borosilicate glass, alumina silicate glass, and soda-lime glass whose surface is coated with silica; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate; A thin film of aluminum, silver, silver/copper/palladium alloy, etc. is formed on the substrate. Other color filter layers, resin layers, transistors, circuits, and the like may be formed on these substrates. Alternatively, a substrate obtained by subjecting a silicon substrate to HMDS (hexamethyldisilazane) treatment may be used.
  • HMDS hexamethyldisilazane
  • each color pixel by the photolithographic method can be carried out using a known or commonly used apparatus and conditions. For example, it can be produced as follows. First, a colored curable resin composition is applied onto a substrate, dried by heating (pre-baking) and/or dried under reduced pressure to remove volatile components such as solvents, and dried to obtain a smooth colored composition layer. Examples of coating methods include a spin coating method, a slit coating method, a slit and spin coating method, and the like.
  • the temperature for heat drying is preferably 30° C. or higher and 120° C. or lower, more preferably 50° C. or higher and 110° C. or lower.
  • the heating time is preferably 10 seconds or more and 60 minutes or less, more preferably 30 seconds or more and 30 minutes or less.
  • the film thickness of the coloring composition layer is not particularly limited, and may be appropriately selected according to the desired film thickness of the color filter.
  • the colored composition layer is exposed through a photomask to form the desired colored pattern.
  • the pattern on the photomask is not particularly limited, and a pattern suitable for the intended use is used.
  • a mask aligner, a stepper, and other exposure apparatuses are used. It is preferred to use When forming a colored coating film, exposure may be performed without using a photomask.
  • the light source used for exposure is preferably a light source that emits light with a wavelength of 250 nm or more and 450 nm or less. For example, light of less than 350 nm is cut using a filter that cuts this wavelength range, or light near 436 nm, 408 nm, and 365 nm is selectively extracted using a bandpass filter that extracts these wavelength ranges.
  • a filter that cuts this wavelength range
  • light near 436 nm, 408 nm, and 365 nm is selectively extracted using a bandpass filter that extracts these wavelength ranges.
  • a colored pattern is formed on the substrate by developing the exposed colored composition layer in contact with a developer.
  • a developer for example, aqueous solutions of alkaline compounds such as potassium hydroxide, sodium hydrogencarbonate, sodium carbonate, tetramethylammonium hydroxide and the like are preferable.
  • the concentration of these alkaline compounds in the aqueous solution is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.03% by mass or more and 5% by mass or less.
  • the developer may contain a surfactant.
  • the developing method may be any of a puddle method, a dipping method, a spray method, and the like.
  • the substrate may be tilted at any angle during development. The substrate after development is preferably washed with water.
  • the post-baking temperature is preferably 80° C. or higher and 250° C. or lower, more preferably 100° C. or higher and 245° C. or lower.
  • the post-baking time is preferably 1 minute or more and 120 minutes or less, more preferably 2 minutes or more and 30 minutes or less.
  • the colored pattern and colored coating film thus obtained are useful as a color filter.
  • the colored curable resin composition of the present invention it is possible to improve the adhesion of the formed color filter. Further, by using the colored curable resin composition of the present invention, it is possible to preferably reduce the generation of residue during development in the production of color filters.
  • the adhesion is the strength of the adhesion between the color filter and the substrate or the like when the color filter is formed. If the adhesion is low, there is a high possibility that the color filter will be peeled off or chipped.
  • the adhesion of the color filter was evaluated by observing the resulting colored pattern (having a dot pattern) under a microscope and counting the number of dots remaining without being peeled off.
  • the term "residue” refers to foreign matter that does not form a pattern and is observed remaining in an unexposed area when the colored pattern after development is observed using an electron microscope (for example, at a magnification of 25,000). be.
  • the color filter is useful as a color filter used in display devices (for example, liquid crystal display devices, organic EL devices, electronic paper, etc.), solid-state imaging devices, and the like.
  • the resulting copolymer had a weight average molecular weight Mw of 9200, a dispersity of 2.08, and an acid value of 81 mg-KOH/g in terms of solid content.
  • the temperature inside the flask was adjusted to 90 ⁇ 1° C., and an aging reaction was carried out for 6 hours.
  • the reaction solution was cooled to 40° C. or less, and 0.15 parts of a polymerization inhibitor, 42.3 parts of acrylic acid, 2.0 parts of triphenylphosphine, and 68.3 parts of propylene glycol monomethyl ether acetate were added.
  • an addition reaction was carried out at an inside temperature of the flask of 110 ⁇ 1° C. to obtain a resin solution.
  • the polystyrene-equivalent weight average molecular weight Mw and number average molecular weight Mn of the resins obtained in the above synthesis examples were measured using the GPC method under the following conditions. Apparatus; HLC-8120GPC (manufactured by Tosoh Corporation) Column; TSK-GELG2000HXL Column temperature; 40°C Solvent; Tetrahydrofuran Flow rate; 1.0 mL/min Test liquid solid content concentration; 0.001 to 0.01% by mass Injection volume: 50 ⁇ L Detector; RI Standard material for calibration; TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)
  • the ratio (Mw/Mn) of the polystyrene-equivalent weight-average molecular weight and the number-average molecular weight obtained above was defined as the degree of dispersion.
  • pigment dispersion (A-6) C. I. Pigment Blue 15:6 8.4 parts C.I. I. Pigment Violet 23 3.6 parts Acrylic pigment dispersant 3.6 parts Resin B1 4.8 parts Propylene glycol monomethyl ether 0.5 parts Propylene glycol monomethyl ether acetate 79.1 parts were mixed to obtain a pigment dispersion (A-6 ).
  • pigment dispersion (A-7) C. I. Pigment Red 254 8.9 parts C.I. I. Pigment Yellow 139 3.0 parts Acrylic pigment dispersant 2.4 parts Resin B2 1.8 parts Propylene glycol monomethyl ether 5.0 parts Propylene glycol monomethyl ether acetate 78.9 parts were mixed to obtain a pigment dispersion (A-7 ).
  • each component is as follows.
  • Colorant (A-1) Pigment dispersion (A-1) obtained above (in terms of solid content)
  • Colorant (A-2) Pigment dispersion (A-2) obtained above (in terms of solid content)
  • Coloring agent (A-3) Pigment dispersion (A-3) obtained above (in terms of solid content)
  • Colorant (A-4) Pigment dispersion (A-4) obtained above (in terms of solid content)
  • Colorant (A-7) Pigment dispersion (A-7) obtained above (in terms of solid content)
  • Colorant (A-8) Pigment dispersion (A-8) obtained above (in terms of solid content)
  • Colorant (A-9) Pigment dispersion (A-9) obtained above (in terms of solid content)
  • Coloring agent (A-10) Pigment dispersion (
  • Leveling agent F-1): polyether-modified silicone oil (SH8400; manufactured by Dow Corning Toray Co., Ltd.)
  • Solvent E-1): Propylene glycol monomethyl ether acetate
  • Solvent E-2): Propylene glycol monomethyl ether
  • the content of the colorant shown in Tables 9 to 11 is a solid content conversion value that is the total amount of the pigment, the pigment dispersant, and the resin, excluding the solvent content from the pigment dispersion.
  • the content of the alkali-soluble resin shown in Tables 9 to 11 is a solid content conversion value obtained by removing the solvent content from the copolymer (resin) solution.
  • the solvent content shown in Tables 9 to 11 also includes the solvent content derived from the pigment dispersion and the copolymer (resin) solution.
  • HMDS manufactured by Tokyo Chemical Industry Co., Ltd.; hexamethyldisilazane
  • a colored curable resin composition was applied to the HMDS-deposited side of the silicon substrate by spin coating, and then prebaked at 80° C. for 2 minutes to obtain a colored composition layer.
  • the substrate on which the colored composition layer was formed was irradiated with light at an exposure dose of 50 mJ/cm 2 (365 nm standard) using an exposure machine (NSR-2205i11D; manufactured by Nikon Corporation).
  • a photomask (pitch is 1.6 ⁇ m, 2.0 ⁇ m, 4.0 ⁇ m, respectively) for forming a dot pattern of 0.8 ⁇ m, 1.0 ⁇ m, and/or 2.0 ⁇ m square during light irradiation used.
  • the colored composition layer after light irradiation is immersed in an aqueous developer containing 0.1% tetramethylammonium hydroxide at 23 ° C. for 30 seconds and developed, washed with water, and post-baked on a hot plate at 230 ° C. for 10 minutes. A colored pattern after post-baking was obtained.

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JP2014210892A (ja) * 2013-04-22 2014-11-13 昭和電工株式会社 （メタ）アクリレート系ポリマー、該ポリマーを含む組成物及びその用途
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JP2014210892A (ja) * 2013-04-22 2014-11-13 昭和電工株式会社 （メタ）アクリレート系ポリマー、該ポリマーを含む組成物及びその用途
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