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WO2013187493A1 - Composition de résine photosensible colorée - Google Patents

Composition de résine photosensible colorée Download PDF

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Publication number
WO2013187493A1
WO2013187493A1 PCT/JP2013/066414 JP2013066414W WO2013187493A1 WO 2013187493 A1 WO2013187493 A1 WO 2013187493A1 JP 2013066414 W JP2013066414 W JP 2013066414W WO 2013187493 A1 WO2013187493 A1 WO 2013187493A1
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WO
WIPO (PCT)
Prior art keywords
group
carbon atoms
formula
alkyl group
substituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2013/066414
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English (en)
Japanese (ja)
Inventor
拓麻 藤田
象同 金
龍虎 呉
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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Filing date
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Priority to CN201380030406.8A priority Critical patent/CN104350422B/zh
Priority to KR1020147035805A priority patent/KR101995094B1/ko
Publication of WO2013187493A1 publication Critical patent/WO2013187493A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B55/00—Azomethine dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B55/00—Azomethine dyes
    • C09B55/009—Azomethine dyes, the C-atom of the group -C=N- being part of a ring (Image)
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0084—Dispersions of dyes
    • C09B67/0085—Non common dispersing agents
    • C09B67/009—Non common dispersing agents polymeric dispersing agent
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • 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
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • 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
    • G03F7/09—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

Definitions

  • the present invention relates to a colored photosensitive resin composition.
  • the colored photosensitive resin composition is used for producing color filters such as liquid crystal display devices and solid-state imaging devices.
  • a colored photosensitive resin composition a colored photosensitive resin composition containing a thiazole dye as a colorant and an alkali-soluble resin having a phenolic hydroxyl group as a binder resin is known (JP 2008-242325). A).
  • a color filter obtained from the conventionally known colored photosensitive resin composition has not always been sufficiently satisfactory in lightness.
  • the present invention includes the following. [1] A colorant (A), an alkali-soluble resin (B), a polymerizable compound (C), a polymerization initiator (D) and a solvent (E) are contained, and the colorant (A) is represented by the formula (AI And the alkali-soluble resin (B) is derived from at least one monomer (a) selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride.
  • a colored photosensitive resin composition which is a copolymer containing units.
  • X represents a nitrogen atom or CH
  • R 41 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms
  • R 42 represents a hydrogen atom, a cyano group, a carbamoyl group, A carboxyl group or an alkoxycarbonyl group having 1 to 4 carbon atoms
  • R 43 represents an oxygen atom
  • C (CN) 2 C
  • L 1 represents a carbon number 1 to 8 alkyl groups
  • L 1 has a methylene unit, one or two of the methylene units may be substituted with an oxygen atom
  • R 44 to R 46 are each independently ,
  • Alkyl group having an oxygen atom is
  • the colored photosensitive resin composition according to [1] which is a copolymer containing a structural unit derived from the monomer (b) having a cyclic ether structure and an ethylenically unsaturated bond.
  • the monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond is composed of a compound represented by the formula (II) and a compound represented by the formula (III).
  • the colored photosensitive resin composition according to any one of [1] to [3], which is at least one compound selected from the group.
  • R b1 and R b2 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 b1 and X b2 represents a single bond, -R b3 -, * - R b3 -O -, * - R b3 -S- or * -R b3 -NH- the stands, R b3 represents an alkanediyl group having 1 to 6 carbon atoms, * Represents a bond with O.
  • [5] A color filter formed from the colored photosensitive resin composition according to any one of [1] to [4].
  • a display device including the color filter according to [5].
  • R 41 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • R 42 represents a hydrogen atom, a cyano group, a carbamoyl group, a carboxyl group or an alkoxycarbonyl group having 1 to 4 carbon atoms.
  • R 43 represents an oxygen atom, C (CN) 2 , C (CN) COOL 1 or C (COOL 1 ) 2 , and L 1 represents an alkyl group having 1 to 8 carbon atoms. However, when L 1 has a methylene unit, one or two of the methylene units may be substituted with an oxygen atom.
  • R 61 is a hydrogen atom, an amino group, or an alkyl group having 1 to 20 carbon atoms and an alkyl group having 1 to 20 carbon atoms which may be substituted with a halogen atom, and between the methylene groups constituting the alkyl group. It represents an alkyl group having an oxygen atom inserted therein or an aryl group which may be substituted.
  • R 62 represents a hydrogen atom, an amino group, or an alkyl group having 1 to 20 carbon atoms that may be substituted with a halogen atom, an amino group that may be substituted, or an aryl group that may be substituted.
  • R 63 represents an aryl group having 6 to 20 carbon atoms having one or more halogen atoms.
  • R 63 is a group represented by the formula (A-III).
  • R 64 represents a halogen atom.
  • R 65 to R 67 each independently represents a hydrogen atom, a halogen atom, an amino group, or an alkyl group having 1 to 20 carbon atoms that may be substituted with a halogen atom, an amino group that may be substituted, or the number of carbon atoms 1 to 20 alkyl groups each representing an alkyl group having an oxygen atom inserted between methylene groups constituting the alkyl group, an optionally substituted aryl group, or a hydroxyl group.
  • R 68 represents a hydrogen atom or a halogen atom.
  • the colored photosensitive resin composition of the present invention contains a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), and a solvent (E).
  • the colorant (A) includes a compound represented by the formula (AI).
  • the colored photosensitive resin composition of the present invention preferably further contains a leveling agent (F).
  • the colored photosensitive resin composition of the present invention preferably further contains a polymerization initiation assistant (D1).
  • the compound illustrated as each component can be used individually or in combination of multiple types.
  • a thiazole dye represented by the formula (AI) (hereinafter sometimes referred to as “dye (AI)”) may be used alone, or another dye (A1). , Pigment (P), or a mixture thereof.
  • preferred X is a nitrogen atom.
  • Examples of the alkyl group having 1 to 4 carbon atoms represented by R 41 include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, and a t-butyl group.
  • R 41 is preferably an alkyl group having 1 to 3 carbon atoms, more preferably a methyl group.
  • the alkoxycarbonyl group having 1 to 4 carbon atoms represented by R 42 a methoxycarbonyl group, an ethoxycarbonyl group, propoxycarbonyl group, isopropoxycarbonyl group, butoxycarbonyl group, isobutoxycarbonyl group, such as t- butoxycarbonyl group Can be mentioned.
  • Preferred R 42 is a cyano group.
  • L 1 examples include groups represented by the following formulas.
  • * represents a bond.
  • R 43 is an oxygen atom.
  • alkyl group having 1 to 20 carbon atoms which may be substituted with an amino group represented by R 44 to R 46 or a halogen atom include groups represented by the following formulae.
  • * represents a bond.
  • Examples of the optionally substituted amino group represented by R 44 to R 46 include an amino group and a group represented by the following formula.
  • * represents a bond.
  • Examples of the alkyl group having 1 to 20 carbon atoms represented by R 44 to R 46 and having an oxygen atom inserted between methylene groups constituting the alkyl group include groups represented by the following formulae: It is done. In the following formula, * represents a bond.
  • Examples of the optionally substituted aryl group represented by R 44 to R 46 include groups represented by the following formulae. In the following formula, * represents a bond.
  • Preferred R 44 is a methyl group, an ethyl group, or a dialkylmethyl group having 3 to 20 carbon atoms (preferably 4 to 10 carbon atoms) (particularly a di-linear alkylmethyl group).
  • Preferred R 45 is an amino group substituted with two alkyl groups having 1 to 10 carbon atoms (more preferably an alkyl group having 3 to 6 carbon atoms), particularly N-diisopropylamino group, N, N-di- an n-butylamino group, an N, N-di-n-pentylamino group, and an N, N-di-n-hexylamino group.
  • Preferred R 46 is a hydrogen atom, a linear or branched alkyl group having 1 to 8 carbon atoms, a naphthyl group, a phenyl group, one or more halogen atoms (preferably a fluorine atom, a chlorine atom, etc.). And more preferably a hydrogen atom, a branched alkyl group having 3 to 4 carbon atoms (preferably isopropyl group, isopentyl group, tert-butyl group), phenyl group or chlorophenyl group.
  • examples of these dyes (AI) include dyes represented by the formulas (AI-1) to (AI-6).
  • Dye (AI) can be produced, for example, by the method described in JP2839675-B.
  • the dye (AI) is prepared by reacting the compound represented by the formula (BI) with the compound represented by the formula (CI) in the presence of an organic solvent or without a solvent. ) Can be manufactured.
  • R 41 to R 46 each have the same meaning as described above.
  • the dye (AI) can also be obtained by reacting the compound represented by the formula (B-II) with the compound represented by the formula (C-II) in the presence of an organic solvent or without a solvent. It can also be manufactured.
  • R 41 to R 46 each represent the same meaning as described above.
  • the dye (A-I) can also be obtained by reacting the compound represented by the formula (B-III) with the compound represented by the formula (C-II) in the presence of an organic solvent or without a solvent. It can also be manufactured.
  • R 45 to R 46 each represent the same meaning as described above.
  • the dye (AI) can also be obtained by reacting the compound represented by the formula (BI) with the compound represented by the formula (C-III) in the presence of an organic solvent or without a solvent. It can also be manufactured.
  • R 41 to R 44 each represent the same meaning as described above.
  • the amount of the compound represented by the formula (CI) used in the reaction between the compound represented by the formula (BI) and the compound represented by the formula (CI) is represented by the formula (BI).
  • they are 0.5 mol or more and 8 mol or less with respect to 1 mol of compounds represented, More preferably, they are 1 mol or more and 3 mol or less.
  • the amount of the compound represented by the formula (C-II) used in the reaction between the compound represented by the formula (B-II) and the compound represented by the formula (C-II) is represented by the formula (B-II).
  • they are 0.5 mol or more and 8 mol or less with respect to 1 mol of compounds represented, More preferably, they are 1 mol or more and 3 mol or less.
  • the amount of the compound represented by the formula (C-II) used in the reaction between the compound represented by the formula (B-III) and the compound represented by the formula (C-II) is represented by the formula (B-III).
  • they are 0.5 mol or more and 8 mol or less with respect to 1 mol of compounds represented, More preferably, they are 1 mol or more and 3 mol or less.
  • the amount of the compound represented by the formula (C-III) used in the reaction between the compound represented by the formula (BI) and the compound represented by the formula (C-III) is represented by the formula (BI).
  • they are 0.5 mol or more and 8 mol or less with respect to 1 mol of compounds represented, More preferably, they are 1 mol or more and 3 mol or less.
  • Organic solvents include hydrocarbon solvents such as toluene and xylene; halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene and chloroform; alcohol solvents such as methanol, ethanol, isopropanol and butanol; nitrated hydrocarbon solvents such as nitrobenzene; methyl Ketone solvents such as isobutyl ketone; amide solvents such as 1-methyl-2-pyrrolidone; and the like.
  • hydrocarbon solvents such as toluene and xylene
  • halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene and chloroform
  • alcohol solvents such as methanol, ethanol, isopropanol and butanol
  • nitrated hydrocarbon solvents such as nitrobenzene
  • methyl Ketone solvents such as isobutyl ketone
  • amide solvents such as 1-methyl-2-pyrrolidone
  • the amount of the organic solvent used is preferably 1 part or more and 20 parts or less, more preferably 1 part or less with respect to 1 part of the compound represented by the formula (BI), (B-II) or (B-III). 2 parts or more and 10 parts or less.
  • the reaction temperature of each reaction is preferably 30 ° C. to 180 ° C., more preferably 80 ° C. to 130 ° C.
  • the reaction time is preferably 1 hour to 12 hours, more preferably 3 hours to 8 hours.
  • the reaction it is preferable to carry out the reaction in the presence of a condensing agent.
  • the condensing agent include phosphoric acid, polyphosphoric acid, phosphorus oxychloride, sulfuric acid, thionyl chloride and the like.
  • the amount of the condensing agent to be used is preferably 0.1 part or more and 20 parts or less with respect to 1 part of the compound represented by the formula (BI), (B-II) or (B-III). Preferably they are 0.2 part or more and 5 parts or less.
  • the dye (AI) can be taken out by mixing the reaction mixture with an alcohol (for example, methanol or the like) and collecting the precipitated crystals by filtration. It is preferred to add the reaction mixture to the alcohol.
  • the temperature at which the reaction mixture is added is preferably ⁇ 100 ° C. or higher and 50 ° C. or lower, more preferably ⁇ 80 ° C. or higher and 0 ° C. or lower.
  • the crystals collected by filtration are preferably washed with water and then dried.
  • the compounds represented by the formulas (B-I), (B-II) and (B-III) are produced by a known method such as the method described in West German Patent Application P3928243.0, for example. Can do.
  • the compounds represented by the formulas (C-I), (C-II) and (C-III) should be prepared by a known method such as the method described in West German Patent Application P3926770.9. Can do.
  • Dye (AI) has excellent spectral characteristics and can be used alone as a blue pigment in the blue filter layer.
  • a compound represented by the following formula (A-II) is novel, and the compound represented by the formula (A-II) has good heat resistance.
  • the colored photosensitive resin composition containing the compound represented by the formula (A-II) is excellent in heat resistance.
  • X represents a nitrogen atom or CH.
  • R 41 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • R 42 represents a hydrogen atom, a cyano group, a carbamoyl group, a carboxyl group or an alkoxycarbonyl group having 1 to 4 carbon atoms.
  • R 43 represents an oxygen atom, C (CN) 2 , C (CN) COOL 1 or C (COOL 1 ) 2
  • L 1 represents an alkyl group having 1 to 8 carbon atoms.
  • R 61 is a hydrogen atom, an amino group, or an alkyl group having 1 to 20 carbon atoms and an alkyl group having 1 to 20 carbon atoms which may be substituted with a halogen atom, and between the methylene groups constituting the alkyl group. It represents an alkyl group having an oxygen atom inserted therein or an aryl group which may be substituted.
  • R 62 represents a hydrogen atom, an amino group, or an alkyl group having 1 to 20 carbon atoms that may be substituted with a halogen atom, an amino group that may be substituted, or an aryl group that may be substituted.
  • R 63 represents an aryl group having 6 to 20 carbon atoms having one or more halogen atoms.
  • a compound represented by the formula (A-II) in which R 63 is a group represented by the formula (A-III) is preferable, and specifically, the compound is represented by the above formula (AI-6). Pigments.
  • R 64 represents a halogen atom.
  • R 65 to R 67 each independently represents a hydrogen atom, a halogen atom, an amino group, or an alkyl group having 1 to 20 carbon atoms that may be substituted with a halogen atom, an amino group that may be substituted, or the number of carbon atoms 1 to 20 alkyl groups each representing an alkyl group having an oxygen atom inserted between methylene groups constituting the alkyl group, an optionally substituted aryl group, or a hydroxyl group.
  • R 68 represents a hydrogen atom or a halogen atom.
  • Examples of the dye (A1) include oil-soluble dyes, acid dyes, basic dyes, direct dyes, mordant dyes, amine salts of acid dyes, sulfonamide derivatives of acid dyes, and the like, for example, Color Index (The Society). of Dyers and Colorists), and known dyes described in dyeing notes (color dyeing company).
  • azo dye cyanine dye, triphenylmethane dye, xanthene dye, phthalocyanine dye, naphthoquinone dye, quinoneimine dye, methine dye, azomethine dye, squarylium dye, acridine dye, styryl dye, coumarin dye, quinoline And dyes and nitro dyes.
  • organic solvent-soluble dyes are preferably used.
  • C.I. I. Solvent Yellow 4 (hereinafter, the description of CI Solvent Yellow is omitted, and only the number is described), 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99. 162; C. I. Solvent Red 45, 49, 125, 130, 218; C. I. Solvent Orange 2, 7, 11, 15, 26, 56; C. I. Solvent Blue 4, 5, 37, 67, 70, 90; C. I. Solvent Green 1, 4, 5, 7, 34, 35, etc. I. Solvent dyes, C. I.
  • Acid Blue 1 7, 9, 15, 18, 22, 29, 42, 59, 60, 62, 70, 72, 74, 82, 83, 86, 87, 90, 92, 93, 100, 102, 103, 104, 113, 117, 120, 126, 130, 131, 142, 147, 151, 154, 158, 161, 166, 167, 168, 170, 171, 184, 187, 192, 199, 210, 229, 234, 236, 242, 243, 256, 259, 267, 285, 296, 315, 335; C.
  • Acid Green 1 3, 5, 9, 16, 50, 58, 63, 65, 80, 104, 105, 106, 109, etc.
  • Acid dyes 1, 3, 5, 9, 16, 50, 58, 63, 65, 80, 104, 105, 106, 109, etc.
  • Direct dyes C. I. C. such as Disperse Yellow 54, 76
  • Disperse dyes C. I. Basic Red 1, 10; C. I. Basic Blue 1, 3, 5, 7, 9, 19, 24, 25, 26, 28, 29, 40, 41, 54, 58, 59, 64, 65, 66, 67, 68; C. I. C. such as Basic Green 1;
  • R ⁇ 1 > and R ⁇ 2 > represents the phenyl group which may have a substituent each independently.
  • R 3 and R 4 each independently represents a monovalent saturated hydrocarbon group having 1 to 10 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom, —CH 2 — contained in the hydrocarbon group may be replaced by —O—, —CO— or —NR 11 —.
  • R 1 and R 3 may be combined with an adjacent nitrogen atom to form a ring containing a nitrogen atom
  • R 2 and R 4 may be combined with an adjacent nitrogen atom to form a ring containing a nitrogen atom. It may be formed.
  • R 5 is, -OH, -SO 3 H, -SO 3 - Z +, -CO 2 H, -CO 2 - Z +, -CO 2 R 8, -SO 3 R 8 or -SO 2 NR 9 R 10
  • R 6 and R 7 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • m represents an integer of 0 to 4. When m is an integer of 2 or more, the plurality of R 5 may be the same or different.
  • R 8 represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom.
  • Z + represents + N (R 11 ) 4 , Na + or K + .
  • R 9 and R 10 each independently represents a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, and R 9 and R 10 are bonded to each other to form a 3 to 10 member together with a nitrogen atom.
  • a nitrogen-containing heterocycle may be formed.
  • R 11 each independently represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or an aralkyl group having 7 to 10 carbon atoms. ]
  • Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms representing R 8 , R 9 , R 10 and R 11 include, for example, methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl Group, octyl group, nonyl group, decyl group, dodecyl group, hexadecyl group, icosyl group, etc., linear alkyl group having 1 to 20 carbon atoms; isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, isopentyl A branched alkyl group having 3 to 20 carbon atoms such as a group, neopentyl group, 2-ethylhexyl group; 3 carbon atoms such as cyclopropyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group,
  • Examples of —OR 8 include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a 2-ethylhexyloxy group, and an icosyloxy group.
  • Examples of —CO 2 R 8 include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, a hexyloxycarbonyl group, and an icosyloxycarbonyl group.
  • Examples of —SR 8 include a methylsulfanyl group, an ethylsulfanyl group, a butylsulfanyl group, a hexylsulfanyl group, a decylsulfanyl group, and an icosylsulfanyl group.
  • Examples of —SO 2 R 8 include a methylsulfonyl group, an ethylsulfonyl group, a butylsulfonyl group, a hexylsulfonyl group, a decylsulfonyl group, and an icosylsulfonyl group.
  • Examples of —SO 3 R 8 include a methoxysulfonyl group, an ethoxysulfonyl group, a propoxysulfonyl group, a tert-butoxysulfonyl group, a hexyloxysulfonyl group, and an icosyloxysulfonyl group.
  • —SO 2 NR 9 R 10 includes, for example, a sulfamoyl group; N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N- sec-butylsulfamoyl group, N-tert-butylsulfamoyl group, N-pentylsulfamoyl group, N- (1-ethylpropyl) sulfamoyl group, N- (1,1-dimethylpropyl) sulfamoyl group, N- (1,2-dimethylpropyl) sulfamoyl group, N- (2,2-dimethylpropyl) sulfamoyl group, N- (1-
  • R 9 and R 10 may be bonded to each other to form a 3- to 10-membered nitrogen-containing heterocycle together with the nitrogen atom.
  • Examples of the heterocyclic ring include the following.
  • Examples of the monovalent saturated hydrocarbon group having 1 to 10 carbon atoms representing R 3 and R 4 include those having 1 to 10 carbon atoms.
  • the hydrogen atom contained in the monovalent saturated hydrocarbon group having 1 to 10 carbon atoms representing R 3 and R 4 may be substituted with a halogen atom, and —CH 2 — contained in the saturated hydrocarbon group is -O -, - CO- or -NR 11 - may be replaced by.
  • halogen atom a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom are mentioned, for example.
  • saturated hydrocarbon group substituted with a halogen atom include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a perfluoroethyl group, a chlorobutyl group, and the like.
  • alkyl group having 1 to 6 carbon atoms representing R 6 and R 7 examples include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, isopropyl group, isobutyl group, sec-butyl group, tert. -A butyl group, an isopentyl group, a neopentyl group, etc. are mentioned.
  • Examples of the aralkyl group having 7 to 10 carbon atoms representing R 11 include a benzyl group, a phenylethyl group, and a phenylbutyl group.
  • Z + is + N (R 11 ) 4 , Na + or K + , preferably + N (R 11 ) 4 .
  • the + N (R 11 ) 4 at least two of the four R 11 are preferably monovalent saturated hydrocarbon groups having 5 to 20 carbon atoms. Further, the total carbon number of the four R 11 is preferably 20 to 80, more preferably 20 to 60.
  • the phenyl group representing R 1 and R 2 may have a substituent.
  • substituents include a halogen atom, -R 8, -OH, -OR 8 , -SO 3 H, -SO 3 - Z +, -CO 2 H, -CO 2 R 8, -SR 8, -SO 2 R 8 , —SO 3 R 8 and —SO 2 NR 9 R 10 may be mentioned.
  • —R 8 is preferable, and a monovalent saturated hydrocarbon group having 1 to 10 carbon atoms is more preferable.
  • -SO 3 in this case - Z + The, -SO 3 - + N (R 11) 4 are preferred.
  • an unsubstituted monovalent saturated hydrocarbon group having 1 to 10 carbon atoms is preferable, a monovalent saturated hydrocarbon group having 1 to 4 carbon atoms is more preferable, and a methyl group and an ethyl group are preferable. Further preferred.
  • R 1 and R 3 may be combined with an adjacent nitrogen atom to form a ring containing a nitrogen atom
  • R 2 and R 4 may be combined with an adjacent nitrogen atom to form a ring containing a nitrogen atom. It may be formed.
  • the ring containing a nitrogen atom include the following.
  • R 5 -SO 3 H, -SO 3 - Z + and -SO 2 NR 9 R 10 are preferred.
  • R 6 and R 7 are preferably a hydrogen atom, a methyl group and an ethyl group, and more preferably a hydrogen atom.
  • m is preferably an integer of 0 to 2, and more preferably 0 or 1.
  • R 21 , R 22 , R 23 and R 24 each independently represents an alkyl group having 1 to 4 carbon atoms.
  • p and q each independently represents an integer of 0 to 5.
  • p is 2 or more, the plurality of R 23 may be the same or different, and when q is 2 or more, the plurality of R 24 may be the same or different.
  • Examples of the alkyl group having 1 to 4 carbon atoms representing R 21 , R 22 , R 23 and R 24 include a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. Groups and the like.
  • R 21 and R 22 are preferably each independently a methyl group or an ethyl group.
  • R 23 and R 24 are preferably methyl groups.
  • m and n are preferably integers of 0 to 2, and preferably 0 or 1.
  • R 31 and R 32 each independently represents an alkyl group having 1 to 4 carbon atoms.
  • R 33 and R 34 each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • Examples of the alkyl group having 1 to 4 carbon atoms representing R 31 , R 32 , R 33 and R 34 are the same as those described above.
  • R 31 and R 32 are preferably each independently a methyl group or an ethyl group.
  • R 33 and R 34 are preferably each independently a hydrogen atom or a methyl group.
  • Examples of compound (1) include compounds represented by formula (1-1) to formula (1-7), respectively. Especially, the compound represented by Formula (1-1) is preferable at the point which is excellent in the solubility to an organic solvent.
  • Formula (1a) A compound represented by formula (1b) and a compound represented by formula (1c) [In Formula (1b) and Formula (1c), R 1 to R 4 each represent the same meaning as described above. ] And in the presence of an organic solvent or without solvent. From the viewpoint of yield, it is preferable to carry out the reaction without solvent.
  • the reaction temperature is preferably 30 to 180 ° C, more preferably 80 to 130 ° C.
  • the reaction time is preferably 1 hour to 12 hours, more preferably 3 hours to 8 hours.
  • organic solvent examples include hydrocarbon solvents such as toluene and xylene; halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene and chloroform; alcohol solvents such as methanol, ethanol and butanol; nitrated hydrocarbon solvents such as nitrobenzene; methyl isobutyl Ketone solvents such as ketones; amide solvents such as 1-methyl-2-pyrrolidone; and the like.
  • hydrocarbon solvents such as toluene and xylene
  • halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene and chloroform
  • alcohol solvents such as methanol, ethanol and butanol
  • nitrated hydrocarbon solvents such as nitrobenzene
  • methyl isobutyl Ketone solvents such as ketones
  • amide solvents such as 1-methyl-2-pyrrolidone; and the like.
  • the amount of the compound represented by the formula (1b) and the compound represented by the formula (1c) is preferably 1 mol or more and 8 mol or less with respect to 1 mol of the compound represented by the formula (1a). More preferably, it is 1 mol or more and 5 mol or less. You may make it react in steps, respectively, and you may make it react simultaneously.
  • the compound represented by the formula (1b) and the compound represented by the formula (1c) are preferably the same compound in that the production of the compound (1) is easy.
  • the method for obtaining the target compound (1) from the reaction mixture is not particularly limited, and various known methods can be employed.
  • the reaction mixture can be mixed with an acid (for example, acetic acid and the like), and the precipitated crystals can be collected by filtration.
  • the acid is preferably prepared by preparing an aqueous solution of the acid in advance, and then adding the reaction mixture to the aqueous solution.
  • the temperature at which the reaction mixture is added is preferably 10 ° C. or higher and 50 ° C. or lower. Thereafter, it is preferable to stir at the same temperature for about 0.5 to 2 hours.
  • the crystals collected by filtration are preferably washed with water and then dried. Moreover, you may refine
  • the pigment (P) is not particularly limited, and a known pigment can be used. Examples thereof include pigments classified as pigments according to a color index (published by The Society of Dyers and Colorists). Examples of the pigment 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, 137, 138, 139, Yellow pigments such as 147, 148, 150, 153, 154, 166, 173, 194, 214; C. I. Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73; C. I.
  • Red pigments such as CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265; C. I. Blue pigments such as CI Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60; I. Violet color pigments such as CI Pigment Violet 1, 19, 23, 29, 32, 36, 38; C. I. Green pigments such as CI Pigment Green 7, 36, 58; C. I. Brown pigments such as CI Pigment Brown 23 and 25; C. I. And black pigments such as CI Pigment Black 1 and 7.
  • the pigment (P) is preferably a phthalocyanine pigment or a dioxazine pigment, more preferably C.I. I. At least one selected from the group consisting of CI Pigment Blue 15: 6 and CI Pigment Violet 23.
  • the transmission spectrum can be easily optimized, and the light resistance and chemical resistance of the color filter are improved.
  • the pigment is atomized by rosin treatment, surface treatment using a pigment derivative having an acidic group or basic group introduced, graft treatment to the pigment surface with a polymer compound, sulfuric acid atomization method, etc.
  • a treatment, a cleaning treatment with an organic solvent or water for removing impurities, a removal treatment by an ion exchange method of ionic impurities, or the like may be performed.
  • the pigments preferably have a uniform particle size.
  • the pigment can be made into a pigment dispersion in a state of being uniformly dispersed in the pigment dispersant solution by carrying out a dispersion treatment by containing a pigment dispersant. Each pigment may be subjected to a dispersion treatment alone, or a plurality of types may be mixed and dispersed.
  • pigment dispersant examples include cationic, anionic, nonionic, amphoteric, polyester, polyamine, and acrylic pigment dispersants. These pigment dispersants may be used alone or in combination of two or more.
  • pigment dispersant examples include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (manufactured by Geneca Co., Ltd.), EFKA (manufactured by BASF), and Ajispur (Ajinomoto Fine). (Techno Co., Ltd.), Disperbyk (Bic Chemie) and the like.
  • the amount used is preferably 100 parts by mass or less, more preferably 5 parts by mass or more and 50 parts by mass or less with respect to 100 parts by mass of the pigment.
  • the amount of the pigment dispersant used is in the above range, there is a tendency that a pigment dispersion in a uniform dispersion state is obtained.
  • the content of the dye (AI) is preferably 1% by mass or more and 100% by mass or less, and more preferably 10% by mass or more and 100% by mass or less, with respect to the total amount of the colorant (A).
  • the content thereof is preferably 0.5% by mass or more and 80% by mass or less, more preferably 40% by mass or more and 90% by mass or less, with respect to the total amount of the colorant (A). It is.
  • the pigment (P) is included, the content is preferably 35% by mass or more and 99% by mass or less, and more preferably 1% by mass or more and 70% by mass or less with respect to the total amount of the colorant (A). More preferably, it is 1 mass% or more and 50 mass% or less.
  • the content of the colorant (A) is preferably 5% by mass or more and 70% by mass or less, more preferably 5% by mass or more and 60% by mass or less, and further preferably 5% by mass with respect to the total amount of the solid content. % To 50% by mass. When the content of the colorant (A) is within the above range, a desired spectrum and color density can be obtained.
  • total amount of solids refers to the total amount of components obtained by removing the solvent (E) from the colored photosensitive resin composition of the present invention.
  • 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, for example.
  • the alkali-soluble resin (B) (hereinafter sometimes referred to as “resin (B)”) is derived from at least one monomer (a) selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride. A copolymer containing structural units. Examples of such a resin (B) include the following resins [K1] to [K6].
  • Resin [K1] At least one monomer (a) selected from the group consisting of unsaturated carboxylic acid and unsaturated carboxylic acid anhydride (hereinafter sometimes referred to as “(a)”), and having 2 to 4 carbon atoms A copolymer of a monomer (b) having a cyclic ether structure and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b)”); Resin [K2] (a) and (b), monomer (c) copolymerizable with (a) (however, different from (a) and (b)) (hereinafter referred to as “(c)”) In some cases) Resin [K3] Copolymer of (a) and (c); Resin [K4] A resin obtained by reacting (b) with a copolymer of (a) and (c); Resin [K5] A resin obtained by reacting (a) with a copolymer of (b) and (c); Resin [K
  • (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-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyl Unsaturated dicarboxylic acids such as tetrahydrophthalic acid and 1,4-cyclohexene dicarboxylic acid; Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo [2.2.1] hept-2-ene, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene, 5-carboxy-5-methylbicyclo [2.2.1] hept-2-ene, 5-carboxy-5-methylbic
  • (B) is, for example, a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring) and an ethylenically unsaturated bond.
  • (B) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth) acryloyloxy group.
  • (meth) acrylic acid represents at least one selected from the group consisting of acrylic acid and methacrylic acid. Notations such as “(meth) acryloyl” and “(meth) acrylate” have the same meaning.
  • Examples of (b) include a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b1)”), and a single monomer having an oxetanyl group and an ethylenically unsaturated bond.
  • Monomer (b2) (hereinafter sometimes referred to as “(b2)”), monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b3)”), etc. Can be mentioned.
  • (b1) for example, a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter referred to as “(b1-1)”) And a monomer (b1-2) having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as “(b1-2)”).
  • glycidyl (meth) acrylate ⁇ -methylglycidyl (meth) acrylate, ⁇ -ethylglycidyl (meth) acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p -Vinylbenzyl glycidyl ether, ⁇ -methyl-o-vinylbenzyl glycidyl ether, ⁇ -methyl-m-vinylbenzyl glycidyl ether, ⁇ -methyl-p-vinylbenzyl glycidyl ether, 2,3-bis (glycidyloxymethyl) styrene 2,4-bis (glycidyloxymethyl) styrene, 2,5-bis (glycidyloxymethyl) styrene, 2,6-bis (glycidyl (meth
  • Examples of (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celoxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth) acrylate (for example, Cyclomer A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth) acrylate (for example, Cyclomer M100; manufactured by Daicel Corporation), a compound represented by Formula (II), and Formula (III) The compound etc. which are represented by these are mentioned.
  • R a and R b 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. May be.
  • X a and X b is a single bond, -R c -, * - R c -O -, * - represents the R c -S- or * -R c -NH-.
  • R c represents an alkanediyl group having 1 to 6 carbon atoms. * Represents a bond with O.
  • alkyl group having 1 to 4 carbon atoms examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group.
  • Examples of the alkyl group in which a hydrogen atom is substituted with hydroxy include hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 1-hydroxy Examples include a -1-methylethyl group, a 2-hydroxy-1-methylethyl group, a 1-hydroxybutyl group, a 2-hydroxybutyl group, a 3-hydroxybutyl group, and a 4-hydroxybutyl group.
  • R a and R b 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 group examples include methylene group, ethylene group, propane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane- Examples include 1,6-diyl group.
  • X a and X b 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, * —CH 2. CH 2 —O— (* represents a bond with O).
  • Examples of the compound represented by the formula (II) include compounds represented by any one of the formulas (II-1) to (II-15). Among them, formula (II-1), formula (II-3), formula (II-5), formula (II-7), formula (II-9) or formula (II-11) to formula (II-15) A compound represented by formula (II-1), formula (II-7), formula (II-9) or formula (II-15) is more preferred.
  • Examples of the compound represented by the formula (III) include compounds represented by any one of the formulas (III-1) to (III-15). Among them, formula (III-1), formula (III-3), formula (III-5), formula (III-7), formula (III-9) or formula (III-11) to formula (III-15) A compound represented by formula (III-1), formula (III-7), formula (III-9) or formula (III-15) is more preferred.
  • the compound represented by the formula (II) and the compound represented by the formula (III) may be used alone or in combination with the compound represented by the formula (II) and the compound represented by the formula (III). May be.
  • the content ratio of the compound represented by formula (II) and the compound represented by formula (III) is preferably 5:95 to 95: 5, more preferably 10:90 to 5 on a molar basis. 90:10, more preferably 20:80 to 80:20.
  • (B2) is more preferably a monomer having an oxetanyl group and a (meth) acryloyloxy group.
  • (B2) includes 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3-acryloyloxymethyloxetane , 3-methyl-3-methacryloyloxyethyl oxetane, 3-methyl-3-acryloyloxyethyl oxetane, 3-ethyl-3-methacryloyloxyethyl oxetane, 3-ethyl-3-acryloyloxyethyl oxetane, and the like.
  • (B3) is more preferably a monomer having a tetrahydrofuryl group and a (meth) acryloyloxy group.
  • Specific examples of (b3) include tetrahydrofurfuryl acrylate (for example, Biscoat V # 150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like.
  • (B) is preferably (b1) in that the color filter obtained can have higher reliability such as heat resistance and chemical resistance. Furthermore, (b1-2) is more preferable in that the storage stability of the colored photosensitive resin composition is excellent.
  • Examples of (c) include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, and 2-ethylhexyl (meth).
  • (Meth) acrylic acid esters of Hydroxy group-containing (meth) acrylic acid esters such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate; Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, diethyl itaconate; Bicyclo [2.2.1] hept-2-ene, 5-methylbicyclo [2.2.1] hept-2-ene, 5-ethylbicyclo [2.2.1] hept-2-ene, 5- Hydroxybicyclo [2.2.1] hept-2-ene, 5-hydroxymethylbicyclo [2.2.1] hept-2-ene, 5- (2′-hydroxyethyl) bicyclo [2.2.1] Hept-2-ene, 5-methoxybicyclo [2.2.1] hept-2-ene, 5-ethoxybicyclo [2.2.1] hept-2-ene, 5,6-dihydroxybicyclo [2.2 .1] Hept-2
  • styrene vinyltoluene
  • benzyl (meth) acrylate tricyclo [5.2.1.0 2,6 ] decan-8-yl (meth) acrylate
  • N from the viewpoint of copolymerization reactivity and heat resistance.
  • -Phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo [2.2.1] hept-2-ene and the like are preferable.
  • the ratio of the structural unit derived from each is the total structural unit constituting the resin [K1] Structural unit derived from (a); 2 to 60 mol% Structural unit derived from (b); 40 to 98 mol% It is preferable that Structural unit derived from (a); 10 to 50 mol% Structural unit derived from (b); 50 to 90 mol% It is more preferable that When the ratio of the structural unit of the resin [K1] is in the above range, the storage stability of the colored photosensitive resin composition, the developability when forming the colored patterned coating film, and the solvent resistance of the resulting color filter There is a tendency to be superior.
  • Resin [K1] is, for example, a method described in the document “Experimental Methods for Polymer Synthesis” (Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st edition, published on March 1, 1972) and the document Can be produced with reference to the cited references described in 1.
  • a predetermined amount of (a) and (b), a polymerization initiator, a solvent, and the like are placed in a reaction vessel, for example, by substituting oxygen with nitrogen to create a deoxygenated atmosphere, with stirring, The method of heating and heat retention is mentioned.
  • the polymerization initiator, the solvent, and the like used here are not particularly limited, and those usually used in the field can be used.
  • polymerization initiators azo compounds (2,2′-azobisisobutyronitrile, 2,2′-azobis (2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.) Any solvent may be used as long as it dissolves each monomer.
  • the solvent (E) for the colored photosensitive resin composition of the present invention include the solvents described later.
  • the obtained copolymer may use the solution after reaction as it is, a concentrated or diluted solution may be used, and it took out as solid (powder) by methods, such as reprecipitation. Things may be used.
  • a concentrated or diluted solution may be used, and it took out as solid (powder) by methods, such as reprecipitation. Things may be used.
  • the solvent contained in the colored photosensitive resin composition of the present invention as a solvent during the polymerization, the solution after the reaction is used as it is for the preparation of the colored photosensitive resin composition of the present invention. Therefore, the manufacturing process of the colored photosensitive resin composition of the present invention can be simplified.
  • Resin [K2] can be produced, for example, in the same manner as the method described as the production method of resin [K1].
  • Resin [K4] obtains a copolymer of (a) and (c), and (b) has a carboxylic acid and / or carboxylic acid anhydride having (a) a cyclic ether having 2 to 4 carbon atoms. It can manufacture by adding to. First, a copolymer of (a) and (c) is produced in the same manner as described in the method for producing resin [K1]. In this case, it is preferable that the ratio of the structural units derived from each is the same as that described for the resin [K3].
  • the carboxylic acid and / or carboxylic anhydride derived from (a) in the copolymer is reacted with a cyclic ether having 2 to 4 carbon atoms which (b) has.
  • the atmosphere in the flask is replaced from nitrogen to air, and (b) a reaction catalyst of carboxylic acid or carboxylic anhydride and cyclic ether (for example, tris ( Dimethylaminomethyl) phenol, etc.) and a polymerization inhibitor (eg, hydroquinone, etc.) are placed in a flask and reacted, for example, at 60-130 ° C. for 1-10 hours to produce resin [K4].
  • a reaction catalyst of carboxylic acid or carboxylic anhydride and cyclic ether for example, tris ( Dimethylaminomethyl) phenol, etc.
  • a polymerization inhibitor eg, hydroquinone, etc.
  • the amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, per 100 mol of (a). By making it in this range, the storage stability of the colored photosensitive resin composition, the developability when forming the patterned coating film, and the solvent resistance, heat resistance, mechanical strength and sensitivity of the resulting patterned coating film are obtained. The balance tends to be good. Since the reactivity of the cyclic ether is high and unreacted (b) hardly remains, (b1) is preferable as (b) used for the resin [K4], and (b1-1) is more preferable.
  • 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 (a), (b) and (c).
  • the amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass with respect to 100 parts by mass of the total amount of (a), (b) and (c).
  • the reaction conditions such as the charging method, reaction temperature, and time can be appropriately adjusted in consideration of the production equipment and the amount of heat generated by polymerization. Similar to the polymerization conditions, the charging method and the reaction temperature can be adjusted as appropriate in consideration of the production equipment, the amount of heat generated by the polymerization, and the like.
  • Resin [K5] obtains a copolymer of (b) and (c) as a first step in the same manner as in the method for producing resin [K1] described above.
  • the obtained copolymer may be used as it is after the reaction, or may be a concentrated or diluted solution, or may be solid (powder) by a method such as reprecipitation. You may use what was taken out as.
  • the ratio of the structural units derived from (b) and (c) is the total number of moles of all the structural units constituting the copolymer, respectively.
  • the cyclic ether derived from (b) of the copolymer of (b) and (c) is added to the carboxylic acid or carboxylic acid anhydride of (a).
  • Resin [K5] can be obtained by reacting the product.
  • the amount of (a) to be reacted with the copolymer is preferably 5 to 80 mol per 100 mol of (b). Since the reactivity of the cyclic ether is high and unreacted (b) hardly remains, (b1) is preferable as (b) used for the resin [K5], and (b1-1) is more preferable.
  • Resin [K6] is a resin obtained by further reacting carboxylic acid anhydride with resin [K5].
  • Carboxylic anhydride is reacted with a hydroxy group generated by reaction of cyclic ether with carboxylic acid or carboxylic anhydride.
  • Carboxylic anhydrides include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1 2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene anhydride, and the like.
  • the amount of the carboxylic acid anhydride used is preferably 0.5 to 1 mole per 1 mole of the amount (a) used.
  • the resin (B) include 3,4-epoxycyclohexylmethyl (meth) acrylate / (meth) acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 2.6. ] Resin such as decyl (meth) acrylate / (meth) acrylic acid copolymer [K1]; 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 (meth) acrylate / (meth) acrylic acid / N-cyclohexylmaleimide copolymer, 3 , 4-epoxytricyclo [5.2.1.0 2.6] decyl (meth) acrylate / (meth) acrylic acid /
  • the resin (B) is preferably a kind selected from the group consisting of a resin [K1], a resin [K2] and a resin [K3], and more preferably from a group consisting of a resin [K2] and a resin [K3]. It is the kind chosen. With these resins, the colored photosensitive resin composition is excellent in developability. From the viewpoint of adhesion between the colored patterned coating film and the substrate, the resin [K2] is more preferable.
  • the polystyrene equivalent weight average molecular weight of the resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and further preferably 5,000 to 30,000. .
  • the molecular weight distribution [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (B) is preferably 1.1 to 6, and more preferably 1.2 to 4.
  • the acid value of the resin (B) is preferably 50 to 170 mg-KOH / g, more preferably 60 to 150 mg-KOH / g, and still more preferably 70 to 135 mg-KOH / g.
  • the acid value is a value measured as the amount (mg) of potassium hydroxide necessary to neutralize 1 g of the resin (B), and can be determined by titration with an aqueous potassium hydroxide solution, for example.
  • the content of the resin (B) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and further preferably 17 to 55% by mass with respect to the total amount of the solid content.
  • the content of the resin (B) is in the above range, a colored patterned coating film can be formed, and the resolution and remaining film ratio of the colored patterned coating film tend to be improved.
  • 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), and examples thereof include a compound having a polymerizable ethylenically unsaturated bond. Is a (meth) acrylic acid ester compound.
  • Examples of the polymerizable compound having one ethylenically unsaturated bond include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, and N-vinylpyrrolidone. And the above-mentioned (a), (b) and (c).
  • Examples of the polymerizable compound having two ethylenically unsaturated bonds include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, and triethylene glycol di (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 three 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) ) Is
  • the weight average molecular weight of the polymerizable compound (C) is preferably from 150 to 2,900, more preferably from 250 to 1,500.
  • the content of the polymerizable compound (C) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and still more preferably 17 to 55% by mass with respect to the total amount of the solid content. is there.
  • the content ratio of the resin (B) to the polymerizable compound (C) [resin (B): polymerizable compound (C)] is on a mass basis, preferably 20:80 to 80:20, more preferably. Is 35:65 to 80:20.
  • the polymerization initiator (D) is not particularly limited as long as it is a compound capable of generating an active radical, an acid, or the like by the action of light or heat and starting polymerization, and a known polymerization initiator 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 the formula (d1). Hereinafter, * represents a bond.
  • Examples of the O-acyloxime compound include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane.
  • O-acyloxime compounds include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1 At least one selected from the group consisting of -on-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropane-1-one-2-imine is preferred, and N-benzoyloxy -1- (4-Phenylsulfanylphenyl) octane-1-one-2-imine is more preferred.
  • the alkylphenone compound is a compound having a partial structure represented by the formula (d2) or a partial structure represented by the formula (d3).
  • the benzene ring may have a substituent.
  • Examples of the compound having a partial structure represented by the formula (d2) 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] butan-1-one Etc.
  • Commercial products such as Irgacure 369, 907, 379 (above, manufactured by BASF) may be used.
  • Examples of the compound having a partial structure represented by the formula (d3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1- [4- (2 -Hydroxyethoxy) phenyl] propan-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomer of 2-hydroxy-2-methyl-1- (4-isopropenylphenyl) propan-1-one, ⁇ , ⁇ -diethoxy Examples include acetophenone and benzyl dimethyl ketal.
  • the alkylphenone compound is preferably a compound having a partial structure represented by the formula (d2).
  • the biimidazole compound is, for example, a compound represented by the formula (d5).
  • R 53 to R 58 represent an aryl group having 6 to 10 carbon atoms which may have a substituent. ]
  • Examples of the aryl group having 6 to 10 carbon atoms include a phenyl group, a toluyl group, a xylyl group, an ethylphenyl group, a naphthyl group, and the like, and a phenyl group is preferable.
  • Examples of the substituent include a halogen atom and an alkoxy group having 1 to 4 carbon atoms.
  • a halogen atom a fluorine atom, a chlorine atom, a bromine atom, an iodine atom etc. are mentioned, for example, Preferably it is a chlorine atom.
  • Examples of the alkoxy group having 1 to 4 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, and a butoxy group, and a methoxy group is preferable.
  • biimidazole compound examples include 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetraphenylbiimidazole and 2,2′-bis (2,3-dichlorophenyl) -4.
  • 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- (4-diethylamin
  • acylphosphine oxide compound examples include 2,4,6-trimethylbenzoyldiphenylphosphine oxide.
  • benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether; benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl- Benzophenone compounds such as 4′-methyldiphenyl sulfide, 3,3 ′, 4,4′-tetra (tert-butylperoxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone; 9,10-phenanthrenequinone, Examples include quinone compounds such as 2-ethylanthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds. These are preferably used in combination with a polymerization initiation assistant (D1) (particularly
  • the polymerization initiator (D) is preferably 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, and more preferably. Is a polymerization initiator containing an O-acyloxime compound.
  • the content of the polymerization initiator (D) is preferably 0.1 to 40 parts by mass, more preferably 1 to 30 parts per 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). Part by mass.
  • the polymerization initiation assistant (D1) is a compound or a sensitizer used for accelerating the polymerization of the polymerizable compound that has been polymerized by the polymerization initiator. When the polymerization initiation assistant (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.
  • Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 4 2-dimethylhexyl dimethylaminobenzoate, N, N-dimethylparatoluidine, 4,4′-bis (dimethylamino) benzophenone (commonly known as Michler's ketone), 4,4′-bis (diethylamino) benzophenone, 4,4′-bis (Ethylmethylamino) benzophenone and the like can be mentioned, among which 4,4′-bis (diethylamino) benzophenone is preferable.
  • Commercial products such as EAB-F (Hodogaya Chemical Co., Ltd.) may be used.
  • alkoxyanthracene compound examples include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-di.
  • Examples include butoxyanthracene and 2-ethyl-9,10-dibutoxyanthracene.
  • thioxanthone compound examples include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone and the like.
  • carboxylic acid compound examples include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid and the like can be mentioned.
  • the content thereof is preferably 0.1 to 30 parts by mass with respect to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C).
  • the amount is preferably 1 to 20 parts by mass.
  • a solvent (E) is not specifically limited, The solvent normally used in the said field
  • an ester solvent a solvent containing —COO— in the molecule and not containing —O—
  • an ether solvent a solvent containing —O— in the molecule and not containing —COO—
  • an ether ester solvent intramolecular Solvent containing -COO- and -O-
  • ketone solvent solvent containing -CO- in the molecule and not containing -COO-
  • alcohol solvent containing OH in the molecule, -O-,- A solvent not containing CO- and -COO-
  • an aromatic hydrocarbon solvent an amide solvent, dimethyl sulfoxide and the like.
  • ester solvents methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate , Methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, ⁇ -butyrolactone and the like.
  • Ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether , Propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, die Glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, methyl anisole, and the like.
  • ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3-ethoxy Ethyl propionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, Ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl acetate Le acetate, propylene glycol monopropyl ether
  • ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone. Etc.
  • Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.
  • Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, mesitylene and the like.
  • Examples of the amide solvent include N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and the like.
  • solvents may be used alone or in combination of two or more.
  • propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 3-methoxybutyl acetate, 3- Methoxy-1-butanol, 4-hydroxy-4-methyl-2-pentanone, N, N-dimethylformamide, N-methylpyrrolidone and the like are preferable, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethylene glycol monobutyl ether, di Propylene glycol methyl ether acetate, ethyl lactate, 3-methoxy Chill acetate, 3-methoxy-1-butanol, ethyl 3-ethoxypropionate, N-
  • the content of the solvent (E) is preferably 70 to 95% by mass, more preferably 75 to 92% by mass, based on the total amount of the colored photosensitive resin composition.
  • the solid content of the colored photosensitive resin composition is preferably 5 to 30% by mass, more preferably 8 to 25% by mass.
  • Leveling agent (F) examples include silicone surfactants, fluorine surfactants, and silicone surfactants having a fluorine atom. These may have a polymerizable group in the side chain.
  • silicone surfactant examples include a surfactant having a siloxane bond in the molecule.
  • Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade name: manufactured by Toray Dow Corning 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 (made by Momentive Performance Materials Japan GK) .
  • fluorosurfactant examples include surfactants having a fluorocarbon chain in the molecule.
  • Florard (registered trademark) FC430, FC431 manufactured by Sumitomo 3M Co., Ltd.
  • MegaFac (registered trademark) F142D, F171, F172, F173, F177, F183, F183, F554, R30, RS-718-K manufactured by DIC Corporation
  • Ftop registered trademark
  • EF303 EF351, EF352
  • Surflon registered trademark
  • SC101 SC105
  • SC105 Asahi Glass Co., Ltd.
  • E5844 Daikin Fine Chemical Laboratory Co., Ltd.
  • silicone surfactant having a fluorine atom examples include surfactants having a siloxane bond and a fluorocarbon chain in the molecule.
  • Megafac (registered trademark) R08, BL20, F475, F477, F443 (manufactured by DIC Corporation) and the like can be mentioned.
  • the content thereof is preferably 0.001% by mass or more and 0.2% by mass or less, more preferably 0.002%, based on the total amount of the colored photosensitive resin composition. It is not less than 0.1% by mass and more preferably not more than 0.005% by mass and not more than 0.07% by mass.
  • the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.
  • the colored photosensitive resin composition of the present invention includes additives known in the art, such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents, etc., if necessary. May be included.
  • the colored photosensitive resin composition of the present invention is used, for example, as necessary, as a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), and a solvent (E). , A leveling agent (F), a polymerization initiation assistant (D1), and other components can be mixed.
  • the pigment in the case of containing the pigment (P) is preferably mixed with a part or all of the solvent (E) in advance and dispersed using a bead mill or the like until the average particle diameter of the pigment is about 0.2 ⁇ m or less. .
  • the desired colored photosensitive resin composition can be prepared by mixing the remaining components in the pigment dispersion thus obtained so as to have a predetermined concentration.
  • the compound (AI) is preferably prepared in advance by dissolving it in part or all of the solvent solvent (E).
  • the solution is preferably filtered through a filter having a pore size of about 0.01 to 1 ⁇ m.
  • the colored photosensitive resin composition after mixing is preferably filtered with a filter having a pore size of about 0.01 to 10 ⁇ m.
  • Examples of the method for producing a colored patterned coating film from the colored photosensitive resin composition of the present invention include a photolithographic method, an inkjet method, and a printing method. Of these, the photolithographic method is preferable.
  • the photolithographic method is a method in which the colored photosensitive resin composition is applied to a substrate, dried to form a colored composition layer, and the colored composition layer is exposed through a photomask and developed.
  • a colored coating film that is a cured product of the colored composition layer can be formed by not using a photomask and / or not developing during exposure.
  • the colored patterned coating film and the colored coating film thus formed are 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. ⁇ 6 ⁇ m.
  • resin plate such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, silicon
  • aluminum, silver, or a silver / copper / palladium alloy thin film is used.
  • another color filter layer, a resin layer, a transistor, a circuit, and the like may be formed.
  • each color pixel by the photolithographic method can be performed by a known or commonly used apparatus and conditions. For example, it can be produced as follows. First, a colored photosensitive resin composition is applied onto a substrate, dried by heating (pre-baking) and / or drying under reduced pressure to remove volatile components such as a solvent and drying to obtain a smooth colored composition layer. Examples of the coating method include spin coating, slit coating, and slit and spin coating.
  • the temperature at which the heat drying is performed is preferably 30 to 120 ° C, more preferably 50 to 110 ° C.
  • the heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes.
  • drying under reduced pressure it is preferably performed at a temperature of 20 to 25 ° C. under a pressure of 50 to 150 Pa.
  • the film thickness of the colored composition layer is not particularly limited, and may be appropriately selected according to the film thickness of the target color filter.
  • the colored composition layer is exposed through a photomask for forming a desired colored patterned coating film.
  • the pattern on the photomask is not particularly limited, and a pattern according to the intended use is used.
  • the light source used for exposure is preferably a light source that generates light having a wavelength of 250 to 450 nm. For example, light less than 350 nm can be cut using a filter that cuts this wavelength range, and light near 436 nm, 408 nm, and 365 nm can be selectively extracted using a bandpass filter that extracts these wavelength ranges. Or you may. Specific examples include mercury lamps, light emitting diodes, metal halide lamps, halogen lamps, and the like.
  • Use an exposure device such as a mask aligner or a stepper because it can irradiate the entire exposure surface with uniform parallel rays and can accurately align the photomask with the substrate on which the colored composition layer is formed. Is preferred.
  • a colored patterned coating film is formed on the substrate.
  • the unexposed portion of the colored composition layer is dissolved in the developer and removed.
  • the developer for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, tetramethylammonium hydroxide is preferable.
  • concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass.
  • the developer may contain a surfactant.
  • the developing method may be any of paddle method, dipping method, spray method and the like.
  • the substrate may be tilted at an arbitrary angle during development. After development, it is preferable to wash with water.
  • the post-bake temperature is preferably 150 to 250 ° C, more preferably 160 to 235 ° C.
  • the post-bake time is preferably 1 to 120 minutes, more preferably 10 to 60 minutes.
  • a color filter with particularly high brightness can be produced.
  • 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.) and solid-state image sensors.
  • Synthesis example 1 An appropriate amount of nitrogen was passed through a flask equipped with a reflux condenser, a dropping funnel and a stirrer to create a nitrogen atmosphere, and 100 parts of propylene glycol monomethyl ether acetate was added and heated to 85 ° C. with stirring. Next, 19 parts of methacrylic acid, 3,4-epoxytricyclo [5.2.1.0 2,6 ] decan-8-yl acrylate and 3,4-epoxytricyclo [5.2.
  • the obtained resin (B-1 had a weight average molecular weight of 8,000, a molecular weight distribution of 1.98, and an acid value in terms of solid content of 53 mg-KOH / g.
  • the polystyrene-reduced weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by the GPC method under the following conditions.
  • Apparatus HLC-8120GPC (manufactured by Tosoh Corporation) Column; TSK-GELG2000HXL Column temperature: 40 ° C Solvent: THF Flow rate: 1.0 mL / min Test liquid solid content concentration: 0.001 to 0.01% by mass Injection volume: 50 ⁇ L Detector; RI Reference material for calibration; TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (Manufactured by Tosoh Corporation)
  • the polystyrene-converted weight average molecular weight and number average molecular weight ratio (Mw / Mn) obtained above was defined as molecular weight distribution.
  • Example 1 Colorant (A): 26 parts of a thiazole dye represented by the formula (A-I-1); Alkali-soluble resin (B): 53 parts of resin (B-1) (in terms of solid content); Polymerizable compound (C): Dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 16 parts; Polymerization initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF; O-acyloxime compound) 4 parts; Solvent (E): 120 parts of propylene glycol monomethyl ether acetate; Solvent (E): 480 parts of 4-hydroxy-4-methyl-2-pentanone; In addition, 0.15 part of leveling agent (F): poly
  • Comparative Example 1 A colored photosensitive resin composition was obtained by the method described in Example 1 of Patent Document 1.
  • the colored photosensitive resin composition was applied on a 2-inch square glass substrate (# 1737; manufactured by Corning) by spin coating, and then pre-baked at 100 ° C. for 3 minutes to form a colored composition layer. After cooling, using an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.), exposure was performed in an air atmosphere at an exposure amount of 150 mJ / cm 2 (based on 365 nm). A photomask was not used. The colored composition layer after exposure was post-baked in an oven at 180 ° C. for 20 minutes to produce a color filter (film thickness: 0.7 ⁇ m).
  • Example 2 The following reaction was performed in a nitrogen atmosphere. After putting 29.2 parts of potassium thiocyanate and 160.0 parts of acetone into a flask equipped with a condenser and a stirrer, the mixture was stirred at room temperature for 30 minutes. Subsequently, 50.0 parts of o-chlorobenzoic acid chloride was added dropwise over 10 minutes. After completion of the dropwise addition, the mixture was further stirred at room temperature for 2 hours. Next, after the reaction mass was ice-cooled, 35.1 parts of dibutylamine was added dropwise. After completion of dropping, the mixture was further stirred at room temperature for 30 minutes.
  • reaction mass was ice-cooled, and 27.4 parts of a 30% aqueous sodium hydroxide solution was added dropwise. After completion of dropping, the mixture was further stirred at room temperature for 30 minutes. Then, 28.4 parts of chloroacetic acid was added dropwise at room temperature. After completion of dropping, the mixture was stirred for 7 hours under heating and reflux. Next, after allowing the reaction mass to cool to room temperature, the reaction solution was poured into 120.0 parts of tap water, 200 parts of toluene was added, and the mixture was stirred for 30 minutes. Next, stirring was stopped and the mixture was allowed to stand for 30 minutes, whereby it was separated into an organic layer and an aqueous layer.
  • Example 3 Colorant (A): 26 parts of a compound represented by formula (AI-6); Alkali-soluble resin (B): 53 parts of resin (B-1) (in terms of solid content); Polymerizable compound (C): Dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 16 parts; Polymerization initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF; O-acyloxime compound) 4 parts; Solvent (E): 120 parts of propylene glycol monomethyl ether acetate; Solvent (E): 480 parts of 4-hydroxy-4-methyl-2-pentanone; In addition, 0.15 part of leveling agent (F): polyether-modified
  • the colored photosensitive resin composition was applied on a 2-inch square glass substrate (# 1737; manufactured by Corning) by spin coating, and then pre-baked at 100 ° C. for 3 minutes to form a colored composition layer. After cooling, using an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.), exposure was performed in an air atmosphere at an exposure amount of 150 mJ / cm 2 (based on 365 nm). A photomask was not used. The colored composition layer after exposure was post-baked in an oven at 180 ° C. for 20 minutes to produce a color filter (film thickness: 2.2 ⁇ m).
  • the coating film of the obtained colored photosensitive resin composition was heated at 200 ° C. for 20 minutes, and the color difference ( ⁇ Eab *) before and after heating of the coating film was measured using a colorimeter (OSP-SP-200; manufactured by OLYMPUS). When measured, the color difference ( ⁇ Eab *) was 2.1.
  • the coating film of the colored photosensitive resin composition obtained in Example 1 was heated at 200 ° C. for 20 minutes, and the color difference ( ⁇ Eab *) before and after heating of the coating film was measured by a colorimeter (OSP-SP-200; manufactured by OLYMPUS). ), The color difference ( ⁇ Eab *) was 10.1.

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  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne une composition de résine photosensible colorée comprenant un agent colorant (A), une résine soluble dans les alcalis (B), un composé polymérisable (C), un initiateur de polymérisation (D) et un solvant (E), l'agent colorant (A) comprenant un colorant thiazole (A-I), et la résine soluble dans les alcalis (B) est un copolymère contenant une unité constituante dérivée d'au moins un monomère (a) sélectionné dans le groupe comprenant un acide carboxylique insaturé et un anhydre d'acide carboxylique insaturé. [Dans la formule (A-I), X représente un atome d'azote ou CH; R41 représente un atome d'hydrogène ou un groupe alkyle possédant de 1 à 4 atomes de carbone; R42 représenté un atome d'hydrogène, un groupe cyano, un groupe carbamoyl ou analogue; R43 représente un atome d'oxygène, C(CN)2 ou analogue; et R44 à R46 représentent indépendamment un atome d'hydrogène, un groupe alkyle possédant de 1 à 20 atomes de carbone qui peuvent être substitués par un groupe amino ou un atome d'halogène ou analogue.]
PCT/JP2013/066414 2012-06-11 2013-06-07 Composition de résine photosensible colorée Ceased WO2013187493A1 (fr)

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CN201380030406.8A CN104350422B (zh) 2012-06-11 2013-06-07 着色感光性树脂组合物
KR1020147035805A KR101995094B1 (ko) 2012-06-11 2013-06-07 착색 감광성 수지 조성물

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JP2012-131593 2012-06-11
JP2012131593 2012-06-11

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CN (1) CN104350422B (fr)
TW (1) TWI582174B (fr)
WO (1) WO2013187493A1 (fr)

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WO2020026855A1 (fr) 2018-07-30 2020-02-06 キヤノン株式会社 Composé, encre, composition de réserve pour filtre coloré, feuille d'enregistrement de transfert thermosensible et toner
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US11008537B2 (en) 2016-03-03 2021-05-18 Lg Chem, Ltd. Cleaning composition for liquid crystal alignment layer and manufacturing method of liquid crystal alignment layer using the same

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US11008537B2 (en) 2016-03-03 2021-05-18 Lg Chem, Ltd. Cleaning composition for liquid crystal alignment layer and manufacturing method of liquid crystal alignment layer using the same
WO2019142736A1 (fr) 2018-01-17 2019-07-25 キヤノン株式会社 Composition, encre, composition de réserve pour filtre coloré, feuille d'enregistrement de transfert thermosensible, et toner
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CN111308859B (zh) * 2018-12-12 2023-08-01 三星Sdi株式会社 感光性树脂组成物、使用其的感光性树脂层及彩色滤光片

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JP6167680B2 (ja) 2017-07-26
TWI582174B (zh) 2017-05-11
CN104350422A (zh) 2015-02-11
JP2014015607A (ja) 2014-01-30
CN104350422B (zh) 2019-05-17
KR20150030668A (ko) 2015-03-20
TW201410793A (zh) 2014-03-16

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