WO2022234774A1 - Composé - Google Patents

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WO2022234774A1
WO2022234774A1 PCT/JP2022/018223 JP2022018223W WO2022234774A1 WO 2022234774 A1 WO2022234774 A1 WO 2022234774A1 JP 2022018223 W JP2022018223 W JP 2022018223W WO 2022234774 A1 WO2022234774 A1 WO 2022234774A1
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group
formula
compound
parts
meth
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PCT/JP2022/018223
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English (en)
Japanese (ja)
Inventor
弘毅 大垣
廷烋 朴
祐規 石堂
佳亮 井上
裕史 濱木
Original Assignee
住友化学株式会社
東友ファインケム株式会社
住華科技股▲ふん▼有限公司
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Application filed by 住友化学株式会社, 東友ファインケム株式会社, 住華科技股▲ふん▼有限公司 filed Critical 住友化学株式会社
Priority to KR1020237033551A priority Critical patent/KR20240007901A/ko
Priority to CN202280032231.3A priority patent/CN117396563A/zh
Priority to JP2023518661A priority patent/JPWO2022234774A1/ja
Publication of WO2022234774A1 publication Critical patent/WO2022234774A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
    • C07C251/30—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having nitrogen atoms of imino groups quaternised
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • 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
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
    • C09B11/16—Preparation from diarylketones or diarylcarbinols, e.g. benzhydrol
    • 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
    • C09B67/006—Preparation of organic pigments
    • 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
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
    • Y10S430/1055—Radiation sensitive composition or product or process of making
    • Y10S430/114—Initiator containing

Definitions

  • the present invention relates to compounds, colored resin compositions, color filters and display 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 manufactured from colored resin compositions.
  • Various colorants are used as the colored resin composition for forming the color filter, and examples of using compounds represented by the following formula (x1) and formula (x2) as the colorant are known. (Patent Document 1).
  • an object of the present invention is to provide a compound capable of forming a color filter having excellent brightness.
  • R 1 to R 4 and R 13 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent.
  • R 5 to R 12 each independently represent a hydrogen atom, a halogen atom or a hydrocarbon group having 1 to 5 carbon atoms which may have a substituent.
  • T 1 represents an optionally substituted divalent aromatic hydrocarbon group.
  • T 2 represents an optionally substituted divalent aromatic hydrocarbon group or an optionally substituted divalent aromatic heterocyclic group.
  • L 1 represents an optionally substituted C 1-12 a-valent aliphatic hydrocarbon group or a group represented by formula (i).
  • T 3 represents an optionally substituted a-valent aromatic hydrocarbon group or an optionally substituted a-valent aromatic heterocyclic group.
  • L 2 represents an optionally substituted C 1-5 divalent aliphatic hydrocarbon group. * represents a bond with T2.
  • R 1 and R 3 represent an optionally substituted phenyl group
  • R 2 and R 4 represent a hydrocarbon group having 2 to 10 carbon atoms, [1], wherein the phenyl groups of R 1 and R 3 have an alkyl group of 1 to 4 carbon atoms in at least one of the two bonding positions ortho to the N bonding to the phenyl group.
  • Compound. [3] A colored resin composition containing a coloring agent and a resin, wherein the coloring agent contains the compound according to [1] or [2]. [4] The colored resin composition according to [3], further comprising a polymerizable compound and a polymerization initiator.
  • [5] A color filter formed from the colored resin composition according to [3] or [4].
  • [6] A display device including the color filter of [5].
  • the compound of the present invention is a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)).
  • compound (I) The present invention will be described in detail below using formula (I), and compound (I) also includes tautomers of formula (I).
  • R 1 to R 4 and R 13 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent.
  • R 5 to R 12 each independently represent a hydrogen atom, a halogen atom or a hydrocarbon group having 1 to 5 carbon atoms which may have a substituent.
  • T 1 represents an optionally substituted divalent aromatic hydrocarbon group.
  • T 2 represents an optionally substituted divalent aromatic hydrocarbon group or an optionally substituted divalent aromatic heterocyclic group.
  • L 1 represents an optionally substituted C 1-12 a-valent aliphatic hydrocarbon group or a group represented by formula (i).
  • a represents an integer of 2 or more.
  • b and c independently represent an integer of 1 or more.
  • T 3 represents an optionally substituted a-valent aromatic hydrocarbon group or an optionally substituted a-valent aromatic heterocyclic group.
  • L 2 represents an optionally substituted C 1-5 divalent aliphatic hydrocarbon group. a has the same meaning as above. * represents a bond with T2. ]
  • the hydrocarbon groups having 1 to 10 carbon atoms represented by R 1 to R 4 and R 13 include aliphatic hydrocarbon groups and aromatic hydrocarbon groups.
  • Aliphatic hydrocarbon groups may be saturated or unsaturated and may be linear or alicyclic.
  • saturated or unsaturated chain hydrocarbon groups include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n - nonyl group, linear alkyl group such as n-decyl group; isopropyl group, (1-ethyl) propyl group, isobutyl group, sec-butyl group, tert-butyl group, (1-ethyl) butyl group, (2 -ethyl) butyl group, (1-propyl) butyl group, isopentyl group, neopentyl group, tert-pentyl group, (2-methyl) pentyl group, (1-ethyl) pentyl group, (3-ethyl) pentyl group, ( 1-propyl)pentyl group, (1
  • saturated or unsaturated alicyclic hydrocarbon groups include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups; cyclohexenyl groups (eg, cyclohex-2-ene , cyclohex-3-ene), cycloheptenyl group and cyclooctenyl group; norbornyl group, adamantyl group, bicyclo[2.2.2]octyl group and the like.
  • cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups
  • cyclohexenyl groups eg, cyclohex-2-ene , cyclohex-3-ene
  • Aromatic hydrocarbon groups include aryl groups such as phenyl, 1-naphthyl and 2-naphthyl groups; o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl and 3-ethylphenyl group, 4-ethylphenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3, 5-dimethylphenyl group, 2,4,6-trimethylphenyl group, 2-methyl-6-ethylphenyl group, 2,6-diethylphenyl group, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl Alkylaryl groups such as groups, 2-methyl-6-isopropylphenyl groups, 4-butylphenyl
  • the hydrocarbon group having 1 to 10 carbon atoms is a combination of two or more chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups listed above, as long as the upper limit of the carbon number is 10.
  • groups include, for example, aralkyl groups such as a benzyl group, a phenethyl group and a 1-methyl-1-phenylethyl group; arylalkenyl groups such as a phenylethenyl group (phenylvinyl group); and arylalkynyl groups such as a phenylethynyl group.
  • Examples of the substituent that the hydrocarbon group having 1 to 10 carbon atoms may have include a halogen atom, a hydroxy group, an alkoxy group, a formyl group, a substituted or unsubstituted and at least one selected from the group consisting of an amino group, a nitro group, a cyano group, --SO 3 ⁇ , and --SO 3 M, where M represents a hydrogen atom or an alkali metal atom.
  • the halogen atom includes a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • alkoxy group include alkoxy groups having 1 to 4 carbon atoms such as methoxy, ethoxy, propoxy and butoxy.
  • substituted amino group include amino groups having one or two hydrocarbon groups, and examples of the hydrocarbon group include the groups exemplified above as the hydrocarbon groups having 1 to 10 carbon atoms.
  • substituted amino groups include N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N,N-dipropylamino group, N-isopropylamino group, N,N-diisopropylamino group, N-phenylamino group, N,N-diphenylamino group, N,N-ethylmethylamino group, N,N-methylphenylamino group, N,N- An ethylphenylamino group and the like can be mentioned.
  • alkali metal atoms examples include sodium and potassium.
  • Halogen atoms represented by R 5 to R 12 include fluorine, chlorine, bromine and iodine atoms.
  • Examples of the hydrocarbon groups having 1 to 5 carbon atoms represented by R 5 to R 12 include aliphatic hydrocarbon groups having 1 to 5 carbon atoms.
  • groups having 1 to 5 carbon atoms can be mentioned.
  • Examples of the substituent that the hydrocarbon group having 1 to 5 carbon atoms may have include the groups exemplified as the substituent A.
  • the divalent aromatic hydrocarbon group represented by T 1 and T 2 is a group in which two hydrogen atoms directly bonded to carbon atoms constituting the ring are substituted for 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, for example, a benzene ring, a naphthalene ring, an anthracene ring, and at least one structure in which one hydrogen atom is replaced with a hydrocarbon group.
  • hydrocarbon group examples include the groups exemplified as the hydrocarbon groups having 1 to 10 carbon atoms represented by R 1 to R 4 and R 13 described above, preferably saturated chain hydrocarbon groups, aryl groups, or an alkylaryl group, more preferably a saturated chain hydrocarbon group having 1 to 4 carbon atoms.
  • the number of hydrocarbon groups bonded to the aromatic hydrocarbon ring is preferably 0-4, more preferably 0-3.
  • divalent aromatic hydrocarbon group include groups represented by the following formulas (Ta-1) to (Ta-8).
  • the divalent aromatic heterocyclic group represented by T 2 is a group in which two hydrogen atoms directly bonded to the atoms constituting the ring in the aromatic heterocyclic ring are replaced with bonds.
  • the aromatic heterocyclic ring constituting the divalent aromatic heterocyclic group may be either a monocyclic ring or a condensed ring, such as pyrrole ring, oxazole ring, pyrazole ring, imidazole ring, thiazole ring, furan ring, thiophene ring, Pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, indole ring, benzimidazole ring, benzothiazole ring, quinoline ring, benzofuran ring, and structures in which at least one hydrogen atom of these aromatic heterocycles is replaced with a hydrocarbon group etc.
  • hydrocarbon group examples include the groups exemplified as the hydrocarbon groups having 1 to 10 carbon atoms represented by R 1 to R 4 and R 13 described above, preferably saturated chain hydrocarbon groups, aryl groups, or an alkylaryl group.
  • the number of hydrocarbon groups bonded to the aromatic heterocycle is preferably 0-4, more preferably 0-3.
  • Examples of the substituent that the divalent aromatic hydrocarbon group and the divalent aromatic heterocyclic group may have include the groups exemplified as the substituent A.
  • the a-valent aliphatic hydrocarbon group having 1 to 12 carbon atoms represented by L 1 is a group in which a hydrogen atoms constituting an aliphatic hydrocarbon are replaced with bonds. The a bonds are preferably present on different carbon atoms.
  • the a-valent aliphatic hydrocarbon group includes an a-valent chain hydrocarbon group, an a-valent alicyclic hydrocarbon group, and an a-valent group obtained by combining a chain hydrocarbon group and an alicyclic hydrocarbon group. etc.
  • the a-valent chain hydrocarbon group may be saturated or unsaturated, but is preferably an a-valent saturated chain hydrocarbon group.
  • a-valent saturated chain hydrocarbon groups include methylene group, ethylene group, propane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5 -alkanediyl groups such as diyl group and hexane-1,6-diyl group; alkanetriyl groups such as groups represented by formulas (a-1) to (a-2) below; formula (a-3) below An alkanetetrayl group such as a group represented by;
  • the a-valent chain hydrocarbon group preferably has 1 to 8 carbon atoms, more preferably 1 to 6 carbon atoms.
  • the a-valent alicyclic hydrocarbon group may be saturated or unsaturated, but is preferably an a-valent saturated alicyclic hydrocarbon group.
  • the a-valent saturated alicyclic hydrocarbon group includes divalent saturated alicyclic hydrocarbons such as cyclohexyl-1,2-diyl group, cyclohexyl-1,4-diyl group and norbornane-2,5-diyl group. group; trivalent saturated alicyclic hydrocarbon group such as cyclohexyl-1,3,5-triyl group; tetravalent saturated alicyclic hydrocarbon group such as cyclohexyl-1,2,4,5-tetrayl group; etc.
  • the a-valent alicyclic hydrocarbon group preferably has 3 to 10 carbon atoms, more preferably 3 to 6 carbon atoms.
  • the a-valent group in which a chain hydrocarbon group and an alicyclic hydrocarbon group are combined is an a-valent group in which at least one chain hydrocarbon group and at least one saturated alicyclic hydrocarbon group are combined. and examples thereof include groups represented by the following formulas (a-4) to (a-7).
  • Examples of the substituent that the a-valent aliphatic hydrocarbon group having 1 to 12 carbon atoms may have include the groups exemplified as the substituent A.
  • L 1 may be a group represented by formula (i).
  • the a-valent aromatic hydrocarbon group represented by T 3 is an aromatic hydrocarbon ring in which a hydrogen atoms directly bonded to carbon atoms constituting the ring are replaced with bonds. It is a base.
  • the aromatic hydrocarbon ring constituting the a-valent aromatic hydrocarbon group include the structures explained as the aromatic hydrocarbon ring constituting the above-mentioned divalent aromatic hydrocarbon group.
  • the a-valent aromatic heterocyclic group represented by T 3 is an aromatic heterocyclic group in which a hydrogen atoms directly bonded to atoms constituting the ring are replaced with bonds. is.
  • the aromatic heterocyclic ring that constitutes the a-valent aromatic heterocyclic group include the structures described as the aromatic heterocyclic ring that constitutes the above-mentioned divalent aromatic heterocyclic group.
  • Examples of the substituent that the a-valent aromatic hydrocarbon group and the a-valent aromatic heterocyclic group may have include the groups exemplified as the substituent A.
  • the divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by L 2 includes a divalent chain hydrocarbon group having 1 to 5 carbon atoms, a chain hydrocarbon group having 1 to 5 carbon atoms, Divalent alicyclic hydrocarbon groups are mentioned.
  • the divalent chain hydrocarbon group may be saturated or unsaturated, but is preferably a bivalent saturated chain hydrocarbon group.
  • Divalent saturated chain hydrocarbon groups include methylene group, ethylene group, propane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5 alkanediyl groups such as -diyl group.
  • the divalent alicyclic hydrocarbon group may be saturated or unsaturated, but is preferably a divalent saturated alicyclic hydrocarbon group.
  • divalent saturated alicyclic hydrocarbon groups include cyclopropyl-1,2-diyl group and cyclobutyl-1,3-diyl group.
  • Examples of the substituent that the divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms may have include the groups exemplified as the substituent A.
  • L i1 to L i5 each independently represent a divalent saturated chain hydrocarbon group having 1 to 5 carbon atoms.
  • L i1 and L i2 and L i3 to L i5 may be the same or different, but are preferably the same.
  • the c-valent anion represented by X c- includes known anions, specifically, fluoride ion, chloride ion, bromide ion, halide ion such as iodide ion, boron-containing anion, Examples include aluminum-containing anions, fluorine-containing anions, and anions containing at least one element selected from the group consisting of tungsten, molybdenum, silicon and phosphorus and oxygen as essential elements.
  • Examples of boron-containing anions and aluminum-containing anions include anions represented by the following formula (4).
  • W 1 and W 2 each independently represent a group having two substituents formed by releasing protons from a monovalent proton-donating substituent.
  • M represents boron or aluminum.
  • the group having two substituents formed by releasing protons from a monovalent proton-donating substituent includes compounds having at least two monovalent proton-donating substituents (e.g., hydroxy group, carboxylic acid group, etc.). groups in which protons are released from each of two proton-donating substituents.
  • Examples of the compound include catechol optionally having substituents, 2,3-dihydroxynaphthalene optionally having substituents, 2,2'-biphenol optionally having substituents, substituents 3-hydroxy-2-naphthoic acid optionally having a substituent, 2-hydroxy-1-naphthoic acid optionally having a substituent, 1-hydroxy-2-naphthoic acid optionally having a substituent Acid, binaphthol optionally having substituents, salicylic acid optionally having substituents, benzilic acid optionally having substituents or mandelic acid optionally having substituents is preferred.
  • substituents include saturated hydrocarbon groups (eg, alkyl groups, cycloalkyl groups, etc.), halogen atoms, haloalkyl groups, hydroxy groups, amino groups, nitro groups, alkoxy groups, and the like.
  • Salicylic acids which may have a substituent include salicylic acid, 3-methylsalicylic acid, 3-tert-butylsalicylic acid, 3-methoxysalicylic acid, 3-nitrosalicylic acid, 4-trifluoromethylsalicylic acid, 3,5-di- Monoaminosalicylic acids such as tert-butylsalicylic acid, 3-aminosalicylic acid, 4-aminosalicylic acid, 5-aminosalicylic acid, 6-aminosalicylic acid; 3-hydroxysalicylic acid (2,3-dihydroxybenzoic acid), 4-hydroxysalicylic acid (2 monohydroxysalicylic acids such as 5-hydroxysalicylic acid (2,5-dihydroxybenzoic acid), 6-hydroxysalicylic acid (2,6-dihydroxybenzoic acid); 4,5-dihydroxysalicylic acid, 4, dihydroxysalicylic acid such as 6-dihydroxysalicylic acid; monohalosalicylic acid; dihalosalicylic acid such as 3,5-dich
  • Preferred anions among the anions represented by formula (4) include anions represented by the following formula, which have substituents listed in Table 1: anions (BC-1) to anions (BC-24); and anions (BC-25) to anions (BC-28) represented by formulas (BC-25), (BC-26), (BC-27) and (BC-28), respectively, and the like. .
  • the anions represented by formula (4) include anion (BC-1), anion (BC-2), anion (BC-3), anion (BC-25), Anion (BC-26), anion (BC-27) are preferred, anion (BC-1), anion (BC-2), anion (BC-25) are more preferred, anion (BC-1), anion (BC -2) is more preferred.
  • fluorine-containing anions examples include groups represented by the following formulas (6), (7), (8), and (9).
  • W 3 and W 4 each independently represent a fluorine atom or a fluorinated alkyl group having 1 to 4 carbon atoms, or W 3 and W 4 together represents a fluorinated alkanediyl group of ⁇ 4.
  • W 5 to W 7 each independently represent a fluorine atom or a fluorinated alkyl group having 1 to 4 carbon atoms.
  • Y 1 represents an alkanediyl fluoride group having 1 to 4 carbon atoms.
  • Y 2 represents a fluorinated alkyl group having 1 to 4 carbon atoms.
  • a perfluoroalkyl group is preferable as the fluorinated alkyl group having 1 to 4 carbon atoms.
  • the perfluoroalkyl groups include -CF 3 , -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CF(CF 3 ) 2 , -CF 2 CF 2 CF 2 CF 3 , -CF 2 CF(CF 3 ) 2 , -C(CF 3 ) 3 and the like.
  • a perfluoroalkanediyl group is preferable as the alkanediyl fluoride group having 1 to 4 carbon atoms.
  • the perfluoroalkanediyl groups include -CF 2 -, -CF 2 CF 2 -, -CF 2 CF 2 CF 2 -, -C(CF 3 ) 2 -, -CF 2 CF 2 CF 2 CF 2 -, and the like. mentioned.
  • anion represented by formula (6) includes anions represented by formulas (6-1) to (6-6) (hereinafter, “anion (6 -1)” to “anion (6-6)”).
  • anion (7) examples include anion (7-1) represented by the following formula.
  • anion represented by formula (8) includes anions represented by formulas (8-1) to (8-4) (hereinafter “anion (8- 1)” to “anion (8-4)”).
  • anion represented by formula (9) includes anions represented by formulas (9-1) to (9-4) (hereinafter “anion (9- 1)” to “anion (9-4)”).
  • the c-valent anion represented by X c- is at least one anion (that is, a fluorine-containing anion) selected from the group consisting of anion (6), anion (7), anion (8) and anion (9).
  • anion (6-1), the anion (6-2) and the anion (7-1) are preferred, and the anion (6-2) is particularly preferred.
  • Examples of c-valent anions represented by X c- include anions containing at least one element selected from the group consisting of tungsten, molybdenum, silicon and phosphorus, and oxygen as essential elements, and tungsten as an essential element.
  • Anions of contained heteropolyacids or isopolyacids are preferred, and anions of phosphotungstic acids, silicotungstic acids and tungsten isopolyacids are more preferred.
  • Examples of such anions of heteropolyacids or isopolyacids containing tungsten as an essential element include Keggin-type phosphotungstate ion ⁇ -[PW 12 O 40 ] 3 ⁇ and Dawson-type phosphotungstate ion ⁇ -[P 2 .
  • anions other than the anions of heteropolyacids or isopolyacids containing tungsten as an essential element anions consisting of at least one element selected from the group consisting of silicon and phosphorus and oxygen are preferred.
  • Such anions composed of oxygen and at least one element selected from the group consisting of silicon and phosphorus include SiO 3 2- and PO 4 3- .
  • heteropolyanions such as Keggin-type phosphotungstate ions, Dawson-type phosphotungstate ions, and Keggin-type silicotungstate ions, and isopolyanions such as [W 10 O 32 ] 4- are preferred because of their ease of synthesis and post-treatment. preferable.
  • a plurality of R 1 to R 13 , T 1 , T 2 and L 1 may be the same or different, but are preferably the same.
  • R 1 to R 4 are each independently an optionally substituted saturated chain hydrocarbon group having 1 to 10 carbon atoms, an optionally substituted aryl having 6 to 10 carbon atoms or an optionally substituted alkylaryl group having 7 to 10 carbon atoms.
  • R 1 and R 3 are each independently an optionally substituted C 6-10 aryl group or an optionally substituted C 7-10 alkylaryl and R 2 and R 4 are each independently a saturated chain hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, preferably R 1 and R 3 are each independently an optionally substituted phenyl group, and R 2 and R 4 are each independently an optionally substituted carbon It is more preferably a saturated chain hydrocarbon group of number 1 to 10, R 1 and R 3 are each independently a phenyl group that may have a substituent, and at least one of the two bonding positions ortho to the N bonded to the phenyl group is a group having an alkyl group having 1 to 4 carbon atoms, and R 2 and R 4 are each independently a saturated chain hydrocarbon group having 1 to 6 carbon atoms and optionally having a substituent; It is even more preferable to have R 1 and R 3 are each independently a phenyl group that may have a substituent, and at least one of
  • a group having up to 3 alkyl groups, and R 2 and R 4 are each independently a saturated chain hydrocarbon group having 2 to 6 carbon atoms, which may have a substituent.
  • the substituents that the phenyl group may have include an alkyl group having 1 to 4 carbon atoms, a halogen atom, a hydroxy group, an alkoxy group, a formyl group, a substituted or unsubstituted amino group, a nitro group, at least one or more selected from the group consisting of cyano group, —SO 3 ⁇ , and —SO 3 M (where M is the same as above), among which alkyl groups having 1 to 4 carbon atoms, halogen atoms, and alkoxy groups; , and --SO 3 -- , and at least one selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and --SO 3 -- .
  • the phenyl group does not have a substituent, or as a substituent, an alkyl group having 1 to 4 carbon atoms, a halogen atom, a hydroxy group, a formyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, - At least one or more substituents selected from the group consisting of SO 3 ⁇ and —SO 3 M (preferably at least one or more substituents selected from the group consisting of an alkyl group having 1 to 4 carbon atoms and —SO 3 — only substituents), the brightness of the resulting color filter can be further enhanced.
  • the light resistance can be improved.
  • the substitution position of the alkoxy group (preferably methoxy group) is not particularly limited, but the effect of improving the light resistance can be further enhanced by bonding to the position para to N bonded to the phenyl group.
  • each of R 1 and R 3 independently represents any one of the groups represented by formulas (r1) to (r3).
  • One or more hydrogen atoms of the groups represented by formulas (r1) to (r3) may be substituted with --SO 3 -- .
  • R r1 to R r4 each independently represent an alkyl group having 1 to 4 carbon atoms. * indicates a bond.
  • R r1 to R r4 are preferably methyl groups.
  • R 5 to R 12 are preferably hydrogen atoms.
  • R 13 is preferably a hydrogen atom or an optionally substituted hydrocarbon group having 1 to 6 carbon atoms, more preferably a hydrogen atom or an optionally substituted carbon atom of 1 to 6 saturated chain hydrocarbon groups, more preferably a hydrogen atom, a methyl group, an ethyl group, an n-propyl group or an isopropyl group.
  • the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group represented by T 1 includes a benzene ring, a naphthalene ring, or at least one hydrogen atom of these rings having 1 to 10 carbon atoms (preferably A structure in which the saturated chain hydrocarbon group of 1 to 4) is substituted is preferable.
  • T 1 is more preferably any one of the groups represented by the above formulas (Ta-1) to (Ta-8), and particularly preferably the group represented by the above formula (Ta-8).
  • T 2 is preferably a divalent aromatic hydrocarbon group which may have a substituent
  • the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group includes a benzene ring, A naphthalene ring or a structure in which at least one hydrogen atom of these rings is replaced with a saturated chain hydrocarbon group having 1 to 10 carbon atoms (preferably 1 to 4) is preferable, and a benzene ring or a benzene ring has A structure in which at least one hydrogen atom is replaced with a saturated chain hydrocarbon group having 1 to 4 carbon atoms is more preferable.
  • T 2 is more preferably any one of the groups represented by the following formulas (Tb-1) to (Tb-10), and the following formulas (Tb-3), (Tb-5), (Tb- 6), (Tb-9), and (Tb-10), more preferably any one of the groups represented by the following formulas (Tb-5), (Tb-6), (Tb-9), Any group represented by (Tb-10) is particularly preferred.
  • L 1 is an a-valent aliphatic hydrocarbon group having 1 to 8 carbon atoms which may have a substituent, or in the group represented by formula (i), T 3 has a substituent is an a-valent aromatic hydrocarbon group which may be substituted, preferably a group in which L 2 is a divalent saturated chain hydrocarbon group having 1 to 5 carbon atoms, optionally having a substituent an alkanediyl group having a number of 1 to 6, an optionally substituted divalent saturated alicyclic hydrocarbon group having 3 to 10 carbon atoms, or a group represented by the above formula (i1) or (i2) is more preferably an optionally substituted C 1-6 alkanediyl group, an optionally substituted C 3-10 divalent saturated alicyclic hydrocarbon or groups represented by the following formulas (i-1) to (i-4).
  • the c-valent anion represented by X c- is a halide ion or an anion containing at least one element selected from the group consisting of tungsten, molybdenum, silicon and phosphorus and oxygen as essential elements. is preferably a halide ion, or an anion of a heteropolyacid or isopolyacid containing tungsten as an essential element, more preferably a halide ion, a Keggin-type phosphotungstate ion, or a Dawson-type phosphotungstate ion .
  • the substituent (ie, substituent A) possessed by compound (I) is selected from the group consisting of a halogen atom, a hydroxy group, an alkoxy group, a substituted or unsubstituted amino group, —SO 3 ⁇ , and —SO 3 M. and more preferably at least one selected from the group consisting of a halogen atom, an alkoxy group, —SO 3 ⁇ , and —SO 3 M.
  • a is preferably an integer of 2 or more and 6 or less, more preferably an integer of 2 or more and 4 or less, and still more preferably 2 or 3.
  • c is usually 1 to 14, preferably 1 to 12, more preferably 1 to 10, even more preferably 1 to 6, and particularly preferably 1 to 4.
  • e is an integer of 0 or more, preferably 0 or more and (a+1) or less, more preferably 0 or more and a or less, still more preferably 0 or a.
  • d is 1 or more
  • X c- is an anion containing at least one element selected from the group consisting of tungsten, molybdenum, silicon and phosphorus and oxygen as essential elements, and d is 1. above and e is 0 is preferred.
  • Compound (I) is preferably a compound represented by formula (I-1) or formula (I-2).
  • R 101 and R 103 are each independently an optionally substituted phenyl group
  • R 102 and R 104 are each independently a saturated chain hydrocarbon group having 1 to 10 carbon atoms which may have a substituent
  • R 105 to R 112 are hydrogen atoms
  • R 113 is a hydrogen atom or an optionally substituted saturated chain hydrocarbon group having 1 to 6 carbon atoms
  • T 101 and T 102 are optionally substituted divalent aromatic hydrocarbon groups, wherein the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group is a benzene ring, A naphthalene ring, or a structure in which at least one hydrogen atom of these rings is replaced with a saturated chain hydrocarbon group having 1 to 4 carbon atoms
  • L 101 is an a101-valent aliphatic hydrocarbon group having 1 to 8 carbon atoms which may have a substituent, or in the group represented by formula (i), T 3 has a substituent is a monovalent aromatic hydrocarbon group which may be a
  • R 201 and R 203 are each independently a phenyl group which may have a substituent;
  • R 202 and R 204 are each independently a saturated chain hydrocarbon group having 1 to 10 carbon atoms which may have a substituent;
  • R 205 to R 212 are hydrogen atoms,
  • R 213 is a hydrogen atom or an optionally substituted saturated chain hydrocarbon group having 1 to 6 carbon atoms,
  • T 201 and T 202 are optionally substituted divalent aromatic hydrocarbon groups, wherein the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group is a benzene ring, A naphthalene ring, or a structure in which at least one hydrogen atom of these rings is replaced with a saturated chain hydrocarbon group having 1 to 4 carbon atoms,
  • L 201 is an a201-valent aliphatic hydrocarbon group having 1 to 8 carbon atoms which may have a substituent, or in the group represented by formula (i),
  • T 3 has a substituent a
  • substituents that the phenyl group represented by R 101 , R 103 , R 201 and R 203 may have include alkyl groups having 1 to 4 carbon atoms, halogen atoms, hydroxy groups, alkoxy groups, formyl groups, at least one or more selected from the group consisting of substituted or unsubstituted amino group, nitro group, cyano group, and —SO 3 M (M is a hydrogen atom or an alkali metal atom); is preferably at least one selected from the group consisting of an alkyl group and an alkoxy group having 1 to 4 carbon atoms.
  • the halogen atom, alkoxy group, substituted amino group, and alkali metal atom are the same as those described for the substituent A.
  • R 101 , R 103 , R 201 and R 203 are optionally substituted phenyl groups, at least one of the two bonding positions ortho to the N bonded to the phenyl group; A group having an alkyl group having 1 to 4 carbon atoms on (preferably both) is preferred.
  • R 101 , R 103 , R 201 and R 203 are each independently preferably any of the groups represented by the above formulas (r1) to (r3), from the viewpoint of improving brightness. is more preferably a group represented by the above formula (r1) or (r2), and more preferably a group represented by the above formula (r3) from the viewpoint of improving light resistance.
  • R 102 , R 104 , R 202 and R 204 are preferably an optionally substituted saturated chain hydrocarbon group having 1 to 6 carbon atoms, and a saturated chain hydrocarbon group having 2 to 6 carbon atoms.
  • a hydrogen group is more preferable.
  • Substituents that the saturated chain hydrocarbon groups represented by R 102 , R 104 , R 202 and R 204 may have include halogen atoms, hydroxy groups, alkoxy groups, formyl group, substituted or unsubstituted amino group, nitro group, cyano group, and --SO 3 M (M is a hydrogen atom or an alkali metal atom).
  • the halogen atom, alkoxy group, substituted amino group, and alkali metal atom are the same as those described for the substituent A.
  • Examples of the substituent which the saturated chain hydrocarbon group having 1 to 6 carbon atoms represented by R 113 and R 213 may have include the groups described as the substituent B.
  • T 101 and T 201 examples of the substituent that the divalent aromatic hydrocarbon group represented by T 101 and T 201 may have include the groups described as the substituent B.
  • T 101 and T 201 are preferably any of the groups represented by the above formulas (Ta-1) to (Ta-8), and are preferably groups represented by the formula (Ta-8). more preferred.
  • substituents that the divalent aromatic hydrocarbon group represented by T 102 and T 202 may have include the groups described as the substituent B, among which a group consisting of a halogen atom and an alkoxy group. At least one or more selected from is preferable.
  • T 102 and T 202 are optionally substituted divalent aromatic hydrocarbon groups, wherein the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group is a benzene ring Or it is preferably a structure in which at least one hydrogen atom of the benzene ring is replaced with a saturated chain hydrocarbon group having 1 to 4 carbon atoms, represented by the above formulas (Tb-1) to (Tb-10) Any of the groups is more preferred, and any of the groups represented by the formulas (Tb-5), (Tb-6), (Tb-9) and (Tb-10) is particularly preferred.
  • an a-valent saturated chain hydrocarbon group having 1 to 8 carbon atoms represented by L 101 and L 201 and an a-valent aromatic group represented by T 3
  • the hydrocarbon group and the substituent that L 2 in formula (i) may have include the groups described as the substituent B.
  • L 101 and L 201 are an optionally substituted C 1-6 alkanediyl group, an optionally substituted C 3-10 divalent saturated alicyclic carbonized It is preferably a hydrogen group or a group represented by the above formula (i1) or (i2).
  • a201 and e201 are preferably the same.
  • the compounds represented by formulas (I-1) and (I-2) preferably have zero charge.
  • the compound represented by formula (I-1) is preferable.
  • Examples of compound (I) include compounds (I-1a-1) to (I-108a-1) and compounds (I-1a-2) to (I- 108a-2), and compounds (I-1b) to (I-108b) represented by the following formula (Ib).
  • the compound represented by formula (Ib) is a compound in which b is 1 and d is 0 among compounds (I).
  • any e2 hydrogen atoms of R 1b to R 13b , T 1b , T 2b and L 1b are substituted with —SO 3 — .
  • H is a hydrogen atom
  • Et is an ethyl group
  • Pr is an n-propyl group
  • r-1 to r-3 are represented by the following formulas (r-1) to (r-3).
  • Ta-8 represents a group represented by the following formula (Ta-8)
  • Tb-5 to Tb-6 and Tb-9 to Tb-10 are represented by the following formulas (Tb-5) to (Tb- 6) and groups represented by (Tb-9) to (Tb-10)
  • l-1 represents a group represented by the following formula (l-1)
  • i-2 and i-4 are represented by the following Groups represented by formulas (i-2) and (i-4) are shown.
  • R 1a , R 3a , R 1b and R 3b are represented by the formula (r-1) or (r-2) are preferable from the viewpoint of improving brightness, and from the viewpoint of improving light resistance.
  • Compounds in which R 1a , R 3a , R 1b , and R 3b are represented by the formula (r-3) are preferred.
  • compounds (I-1a-2) to (I-108a-2) are preferred, and compounds (I-1a-2) to (I-18a-2) and compounds (I-55a-2) to (I-72a-2) are more preferred.
  • Compound (I) can be produced, for example, by the following methods (1) to (3).
  • Compound (I') is represented by, for example, formula (BI) can be produced by reacting a compound represented by Formula (C-I) with a compound represented by Formula (C-I).
  • T 1B represents a group in which a bond different from the bond bonding to the nitrogen atom in T 1 is replaced with a hydrogen atom.
  • the amount of the compound represented by formula (C-I) to be used is preferably 0.5 mol or more and 10 mol or less, more preferably 1 mol, per 1 mol of the compound represented by formula (BI). It is mol or more and 4 mol or less.
  • the reaction temperature 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 1 hour to 8 hours.
  • the above reaction may be carried out in the presence of an organic solvent or in the absence of a solvent, but from the standpoint of yield, it is preferably carried out in an organic solvent.
  • 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; nitrohydrocarbon solvents such as nitrobenzene; ketone solvents such as ketones; amide solvents such as 1-methyl-2-pyrrolidone;
  • the amount of the organic solvent used is preferably 1 part by mass or more and 20 parts by mass or less, more preferably 2 parts by mass or more and 10 parts by mass or less, relative to 1 part by mass of the compound represented by formula (BI). be.
  • Condensing agents include phosphoric acid, polyphosphoric acid, phosphorus oxyhalides such as phosphorus oxychloride, sulfuric acid, and thionyl halides such as thionyl chloride.
  • phosphorus oxyhalide, thionyl halide, or the like is used as a condensing agent and the relationship of formula (z1) is satisfied, compound (I′) in which X c ⁇ is a halide ion can be obtained.
  • a ⁇ be>0 (z1) [In the above formula, a and b have the same meanings as a and b in formula (I).
  • the amount of the condensing agent used is preferably 0.1 parts by mass or more and 20 parts by mass or less, more preferably 0.2 parts by mass or more and 10 parts by mass with respect to 1 part by mass of the compound represented by formula (BI). Part by mass or less.
  • the method for obtaining compound (I') from the reaction mixture is not particularly limited, and various known techniques can be employed. After taking out, the resulting residue may be purified by column chromatography, recrystallization, or the like.
  • compound (I) (hereinafter sometimes referred to as compound (I'')) wherein X c- is an anion other than a halide ion (hereinafter, anion X 1 )
  • compound (I'') can be produced by mixing compound (I′) with an alkali metal salt or protonic acid of anion X 1 .
  • Alkali metals include lithium, sodium and potassium.
  • the amount of the alkali metal salt or protonic acid of the anion X1 to the compound ( I ') is preferably added in a stoichiometric ratio such that the cation in the compound ( I ') and the charge of the anion X1 are balanced.
  • it is preferably 0.5 mol or more and 8 mol or less, more preferably 1 mol or more and 3 mol or less, relative to 1 mol of (I').
  • the compound ( I ') and an alkali metal salt or protonic acid of anion X1 may be mixed either by dissolving them in the following solvent or without dissolving them.
  • Solvents include N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethylsulfoxide, acetonitrile, ethyl acetate, toluene, methanol, ethanol, isopropanol, acetone, tetrahydrofuran, dioxane, water and chloroform. be done.
  • at least one selected from the group consisting of N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethylsulfoxide, methanol, ethanol, isopropanol and water Solvents are preferred.
  • the amount of the solvent to be used is preferably 1 part by mass or more and 30 parts by mass or less, more preferably 2 parts by mass or more and 20 parts by mass or less, relative to 1 part by mass of compound (I').
  • an acid such as acetic acid or hydrochloric acid may be added.
  • the temperature for mixing compound ( I ') and an alkali metal salt or protonic acid of anion X1 is preferably 0°C to 150°C, more preferably 10°C to 120°C, still more preferably 20°C to 100°C.
  • the mixing time is preferably 1 hour to 72 hours, more preferably 2 hours to 24 hours, even more preferably 3 hours to 12 hours.
  • compound (I'') can be obtained by mixing the solutions, optionally stirring for 1 to 3 hours, and then removing the solvent. . If necessary, the obtained compound (I'') may be washed with ion-exchanged water, methanol, or the like.
  • the reaction mixture is mixed with ion-exchanged water, stirred for 1 to 3 hours if necessary, and then the organic layer is obtained by liquid separation to obtain the compound ( I'') can be obtained. If necessary, the solution may be washed with deionized water.
  • Compound (I'') can be obtained by removing the solvent from a solution containing compound (I'').
  • the amount of sulfuric acid used relative to compound (I') should be such that the cation in compound (I') and the charge of --SO 3 -- are balanced. is, for example, 0.5 mol or more and 8 mol or less, preferably 1 mol or more and 3 mol or less.
  • the sulfuric acid may be used as a reaction solvent, and when sulfuric acid is used as a solvent, the amount of sulfuric acid used is, for example, 20 mol or more, preferably 25 mol or more, relative to 1 mol of compound (I'). be.
  • the upper limit of the amount of sulfuric acid to be used is not particularly limited.
  • the mixing temperature of compound (I') and sulfuric acid is preferably 0°C to 150°C, more preferably 10°C to 120°C, even more preferably 20°C to 100°C.
  • the mixing time is preferably 1 hour to 72 hours, more preferably 2 hours to 24 hours, even more preferably 3 hours to 12 hours.
  • a mixture obtained by mixing compound (I') and sulfuric acid can be added to ice water to form a suspension, and then filtered to obtain compound (I'''). Further, if necessary, it may be further purified by a known technique such as recrystallization or fractionation by chromatography.
  • the colored resin composition of the present invention contains a coloring agent (hereinafter sometimes referred to as coloring agent (A)) and a resin (hereinafter sometimes referred to as resin (B)), and the coloring agent is a compound Including (I).
  • the colored resin composition of the present invention further contains a polymerizable compound (hereinafter sometimes referred to as a polymerizable compound (C)) and a polymerization initiator (hereinafter sometimes referred to as a polymerization initiator (D).) is preferred.
  • the colored resin composition of the present invention preferably further contains a solvent (hereinafter sometimes referred to as solvent (E)).
  • the colored resin composition of the present invention may further contain a leveling agent (hereinafter sometimes referred to as leveling agent (F)).
  • the compounds exemplified as each component can be used singly or in combination unless otherwise specified.
  • Colorant (A) contains compound (I).
  • the brightness of the color filter to be obtained is improved, and preferably the thickness of the color filter to be obtained can be reduced.
  • Examples of the compound (I) include the compound (I) described above, and preferred embodiments thereof are also the same.
  • the coloring agent (A) contains a dye other than compound (I) (hereinafter sometimes referred to as dye (A1-1)) and/or a pigment (hereinafter sometimes referred to as pigment (A1-2)). good too.
  • dye (A1-1) a dye other than compound (I)
  • pigment (A1-2) a pigment
  • colorant (A1) the combination of dye (A1-1) and pigment (A1-2) may be referred to as colorant (A1). These may be used alone or in combination of two or more.
  • the dye (A1-1) is not particularly limited as long as it does not include the compound (I), and known dyes can be used. Examples include solvent dyes, acid dyes, direct dyes, mordant dyes, and the like. Dyes include, for example, compounds classified as dyes in the Color Index (published by The Society of Dyers and Colourists) 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, and the like.
  • organic solvent-soluble dyes are preferred.
  • 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.
  • the pigment (A1-2) is not particularly limited as long as it does not include the compound (I), and known pigments can be used.
  • pigments. Pigments classified as pigments include, for example, 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.
  • C. I. Blue pigments such as Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60;
  • C. I. Violet color pigments such as Pigment Violet 1, 19, 23, 32, 36, 38;
  • Green pigments such as Pigment Green 7, 36, 58, 59, 62, 63;
  • C. I. Brown pigments such as Pigment Brown 23 and 25;
  • C. I. black pigments such as Pigment Black 1 and 7;
  • the coloring agent (A1) is preferably a yellow, red or green dye and/or pigment.
  • the coloring agent (A1) may be subjected, if necessary, to rosin treatment, surface treatment using a derivative into which an acidic group or a basic group is introduced, or the like, graft treatment to the surface of the coloring agent (A1) with a polymer compound or the like, sulfuric acid Atomization treatment by an atomization method or the like, washing treatment with an organic solvent, water, or the like for removing impurities, removal treatment by an ion exchange method or the like for ionic impurities, or the like may be performed.
  • the particle size of the colorant (A1) is preferably substantially uniform.
  • the content of the compound (I) is, for example, 1% by mass or more, preferably 2% by mass, relative to the total amount of the colorant (A). or more, more preferably 10% by mass or more, still more preferably 25% by mass or more, and particularly preferably 50% by mass or more.
  • the content of the compound (I) is, for example, less than 100% by mass with respect to the total amount of the colorant (A).
  • the colored resin composition contains the solvent (E)
  • the colored resin composition is prepared using the colorant-containing liquid. may be prepared.
  • the colorant (A) does not dissolve in the solvent (E)
  • the colorant-containing liquid contains the colorant (A) and the solvent (E ) can be prepared by dispersing and mixing.
  • the colorant-containing liquid may contain part or all of the solvent (E) contained in the colored resin composition.
  • the content of solids in the colorant-containing liquid is preferably 0.01% by mass or more and 99.99% by mass or less, more preferably 0.1% by mass or more and 99.9% by mass, relative to the total amount of the colorant-containing liquid. % 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.
  • the coloring agent (A) may be dispersed uniformly in the solution by incorporating 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
  • a resin (B) described later may be used as a dispersant.
  • the amount of the dispersant (solid content) used is usually 1 part by mass or more and 10000 parts by mass or less, preferably 5 parts by mass or more and 5000 parts by mass, relative to 100 parts by mass of the colorant (A). 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.
  • the content of the coloring agent (A) is preferably 0.1% by mass or more and 50% by mass or less, more preferably 0.5% by mass or more and 40% by mass, based on the total solid content of the colored resin composition. or less, more preferably 1% by mass or more and 30% by mass or less.
  • the content of the coloring agent (A) is within the above range, the color density of the color filter is sufficient, and the necessary amount of the resin (B) can be contained in the composition. It is preferable because a pattern with sufficient strength can be formed.
  • the "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 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.
  • Resin [K1] a structural unit derived from at least one monomer (a) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter sometimes referred to as "(a)”); , a copolymer having structural units derived from a monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b)”); Resin [K2]; a structural unit derived from (a), a structural unit derived from (b), and a monomer (c) copolymerizable with (a) (where (a) and (b) are different.) (hereinafter sometimes referred to as "(c)”) and
  • Examples of monomer (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid and o-, m-, 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-6-methylbicy
  • the monomer (b) has 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 (oxolane ring)) and an ethylenically unsaturated bond.
  • a polymerizable compound having 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 referred to as "monomer (b3)” in some cases), etc.
  • the monomer (b1) for example, a monomer having a structure obtained by epoxidizing an unsaturated aliphatic hydrocarbon (hereinafter sometimes referred to as "monomer (b1-1)"), unsaturated alicyclic Examples thereof include monomers having a structure obtained by epoxidizing a hydrocarbon of the formula (hereinafter sometimes referred to as “monomer (b1-2)").
  • the monomer (b1-1) a monomer having a glycidyl group and an ethylenically unsaturated bond is preferred.
  • Specific examples of the monomer (b1-1) include 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
  • Examples of the monomer (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (eg, Celloxide (registered trademark) 2000; manufactured by Daicel Corporation), and 3,4-epoxycyclohexylmethyl.
  • (Meth)acrylate eg, Cychromer (registered trademark) A400; manufactured by Daicel Corporation
  • 3,4-epoxycyclohexylmethyl (meth)acrylate eg, Cychromer (registered trademark) M100; manufactured by Daicel Corporation
  • a compound represented by the formula (BI) a compound represented by the formula (BII), and the like.
  • R a and R b each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group is a hydroxy group. may be substituted with X a and X b each independently represent a single bond, *-R c -, *-R c -O-, *-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 groups having 1 to 4 carbon atoms examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group and tert-butyl group.
  • Alkyl groups in which a hydrogen atom is substituted with hydroxy include, for example, 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 a and R b preferably include 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 group, ethylene group, propane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, A hexane-1,6-diyl group and the like can be mentioned.
  • X a and X b are preferably a single bond, a methylene group, an ethylene group, a *—CH 2 —O— (* represents a bond with O) group, or a *—CH 2 CH 2 —O— group. more preferably a single bond or *--CH 2 CH 2 --O-- group (* 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 (BI-5), formula (BI-7), formula (BI-9) and formula (BI-11) to formula (BI-15) Compounds represented by Formula (BI-1), Formula (BI-7), Formula (BI-9) and Formula (BI-15) are more preferable.
  • Examples of the compound represented by formula (BII) include compounds represented by any one of formulas (BII-1) to (BII-15), and among them, formula (BII-1), formula (BII -3), formula (BII-5), formula (BII-7), formula (BII-9) and formulas (BII-11) to formula (BII-15) are preferred compounds represented by formula (BII- 1), Formula (BII-7), Formula (BII-9) and Formula (BII-15) are more preferred.
  • the compound represented by the formula (BI) and the compound represented by the formula (BII) may be used alone, or the compound represented by the formula (BI) and the compound represented by the formula (BII) may be used in combination. You may When these are used in combination, the content ratio of the compound represented by formula (BI) and the compound represented by formula (BII) is preferably 5:95 to 95:5, more preferably 10: on a molar basis. 90 to 90:10, more preferably 20:80 to 80:20.
  • the monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferable.
  • the monomer (b2) include 3-methyl-3-(meth)acryloyloxymethyloxetane, 3-ethyl-3-(meth)acryloyloxymethyloxetane, 3-methyl-3-(meth)acryloyl oxyethyloxetane, 3-ethyl-3-(meth)acryloyloxyethyloxetane and the like.
  • the monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferable.
  • the monomer (b3) include tetrahydrofurfuryl acrylate (eg, Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like.
  • 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.
  • vinyl group-containing amides such as (meth)acrylamide; esters such as vinyl acetate; dienes such as 1,3-butadiene, isoprene and 2,3-dimethyl-1,3-butadiene; .
  • the ratio of the structural units derived from each of the total structural units constituting the resin [K1] is Structural unit derived from (a); 2 to 60 mol% Structural unit derived from (b); 40 to 98 mol% is preferably Structural unit derived from (a); 10 to 50 mol% Structural unit derived from (b); 50 to 90 mol% is more preferable.
  • the ratio of the structural units of the resin [K1] is within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance of the resulting color filter tend to be excellent. be.
  • the resin [K1] 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 .
  • a polymerization initiator e.g., 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 created, and while stirring, A method of heating and keeping warm can be mentioned.
  • 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, etc.).
  • the solvent any solvent can be used as long as it dissolves each monomer, and examples thereof include the solvents described later as the solvent (E) for the colored resin composition of the present invention.
  • 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 resin composition of the present invention as a solvent during this polymerization, the solution after the reaction can be used as it is for the preparation of the colored resin composition of the present invention.
  • the manufacturing process of the colored resin composition of the present invention can be simplified.
  • the ratio of the structural units derived from each of the total structural units constituting the resin [K2] is Structural unit derived from (a); 2 to 45 mol% Structural units derived from (b): 2 to 95 mol% Structural units derived from (c): 1 to 65 mol% is preferably Structural unit derived from (a); 5 to 40 mol% Structural unit derived from (b); 5 to 80 mol% Structural unit derived from (c); 5 to 60 mol% is more preferable.
  • the ratio of the structural units of the resin [K2] is in the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance and heat resistance of the resulting color filter are improved. And tend to be excellent in mechanical strength.
  • the resin [K2] can be produced, for example, in the same manner as the method for producing the resin [K1].
  • the ratio of the structural units derived from each of the total structural units constituting the resin [K3] is Structural unit derived from (a); 2 to 60 mol% Structural unit derived from (c); 40 to 98 mol% is preferably Structural unit derived from (a); 10 to 50 mol% Structural unit derived from (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 [K1].
  • Resin [K4] is a carboxylic acid and/or carboxylic acid anhydride obtained by obtaining a copolymer of (a) and (c), and having (a) a cyclic ether having 2 to 4 carbon atoms possessed by (b). It can be produced by adding to First, a copolymer of (a) and (c) is produced in the same manner as the method for producing resin [K1]. In this case, the ratio of structural units derived from each is preferably the same ratio as mentioned for resin [K3].
  • part of the carboxylic acid and/or carboxylic anhydride derived from (a) in the copolymer is reacted with the cyclic ether having 2 to 4 carbon atoms of (b).
  • the atmosphere in the flask is replaced from nitrogen to air, and (b) a reaction catalyst (e.g., tris ( dimethylaminomethyl)phenol, etc.) and a polymerization inhibitor (e.g., hydroquinone, etc.) are placed in a flask and reacted at, for example, 60 to 130° C. for 1 to 10 hours to produce resin [K4].
  • a reaction catalyst e.g., tris ( dimethylaminomethyl)phenol, etc.
  • a polymerization inhibitor e.g., 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 setting this range, the storage stability of the colored resin composition, the developability when forming a pattern, and the solvent resistance, heat resistance, mechanical strength and sensitivity balance of the resulting pattern tend to be good. be. Since the cyclic ether has high reactivity and unreacted (b) does not easily remain, (b1) is preferable as (b) used in resin [K4], and (b1-1) is more preferable.
  • the amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b) and (c).
  • the amount of the polymerization inhibitor to be used is preferably 0.001 to 5 parts by weight per 100 parts by weight of the total amount of (a), (b) and (c).
  • 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.
  • a copolymer of (b) and (c) is obtained in the same manner as in the method for producing resin [K1] described above.
  • 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 converted into a solid (powder) by a method such as reprecipitation. You may use what was taken out as.
  • the ratio of structural units derived from (b) and (c) to the total number of moles of all structural units constituting the copolymer is, respectively, Structural unit derived from (b); 5 to 95 mol% Structural unit derived from (c); 5 to 95 mol% is preferably Structural unit derived from (b); 10 to 90 mol% Structural unit derived from (c); 10 to 90 mol% is more preferable.
  • the cyclic ether derived from (b) in the copolymer of (b) and (c) is added to the carboxylic acid or carboxylic anhydride of (a).
  • Resin [K5] can be obtained by reacting substances.
  • the amount of (a) to be reacted with the copolymer is preferably 5 to 80 mol per 100 mol of (b). Since the cyclic ether has high reactivity and unreacted (b) does not easily remain, (b1) is preferable as (b) used in resin [K5], and (b1-1) is more preferable.
  • Resin [K6] is a resin obtained by reacting resin [K5] with a carboxylic acid anhydride. The hydroxy group generated by the reaction of the cyclic ether with the carboxylic acid or carboxylic anhydride is reacted with the carboxylic anhydride.
  • Carboxylic anhydrides include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinyl phthalic anhydride, 4-vinyl phthalic 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 carboxylic acid anhydride to be used is preferably 0.5 to 1 mol per 1 mol of (a).
  • Specific resins (B) 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-epoxytricyclo[ 5.2.1.0 2,6 ]decyl acrylate/(meth)acrylic acid/N-cyclohexylmaleimide/2-hydroxyethyl (meth)
  • the resin (B) is more preferably at least one selected from the group consisting of resin [K1] and resin [K2], and particularly preferably resin [K2].
  • the polystyrene equivalent weight average molecular weight (Mw) of the resin (B) is preferably 1,000 or more and 100,000 or less, more preferably 2,000 or more and 50,000 or less, and still more preferably 3,000 or more. 30,000 or less.
  • the dispersion degree [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the resin (B) is preferably 1 or more and 6 or less, more preferably 1.001 or more and 4 or less, and still more preferably 1.001 or more. 01 or more and 4 or less.
  • the acid value (solid content conversion value) of the resin (B) 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, 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 60 mg-KOH/g or more and 135 mg-KOH/g g or less.
  • the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin, and can be determined by titration with an aqueous potassium hydroxide solution, for example.
  • the content of the resin (B) is preferably 5 to 50% by mass, more preferably 10 to 40% by mass, and still more preferably 15 to 30% by mass in 100% by mass of the solid content of the colored resin composition. is. When the content of the resin (B) is within the above range, the solubility of the unexposed area in the developer tends to be high.
  • 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., as well as 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 even 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 resin composition. , more preferably 10% by mass or more and 80% by mass or less, and still more preferably 12% 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.
  • O-acyloxime compounds 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-(4-phenylsulfanylphenyl)- 3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl -6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethy
  • O-acyl oxime compounds Irgacure (registered trademark) OXE01, OXE02 (manufactured by BASF), N-1919 (manufactured by ADEKA Co., Ltd.), and TR-PBG327 (manufactured by Changzhou Power Electronics New Materials Co., Ltd.), etc. may be used.
  • Irgacure registered trademark
  • OXE01, OXE02 manufactured by BASF
  • N-1919 manufactured by ADEKA Co., Ltd.
  • TR-PBG327 manufactured by Changzhou Power Electronics New Materials Co., Ltd.
  • O-acyloxime compounds 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, and TR-PBG327 (N-acetoxy-1-(4- phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine), N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one- At least one selected from the group consisting of 2-imine and TR-PBG327 (N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclohexyl
  • Alkylphenone compounds include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutane-1- and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one and the like.
  • Commercially available products such as Irgacure (registered trademark) 369, 907, 379 (manufactured by BASF) may be used as the alkylphenone compound.
  • alkylphenone compounds include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, Also included are 1-hydroxycyclohexylphenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, ⁇ , ⁇ -diethoxyacetophenone and benzyl dimethyl ketal.
  • Biimidazole compounds include, for example, 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'-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(trialkoxyphenyl)biimidazole (see, for example, JP-B-48-38403, JP-A
  • Triazine compounds include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine and 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-methoxystyryl)- 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]-1,3,5
  • Acylphosphine oxide compounds include 2,4,6-trimethylbenzoyldiphenylphosphine oxide and the like.
  • Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) may also be used.
  • 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 and 2,4,6-trimethylbenzophenone; 9,10-phenanthrenequinone, 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 aid (D1) (particularly an amine),
  • 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, more preferably It is a polymerization initiator containing an O-acyl oxime compound.
  • the content of the polymerization initiator (D) is preferably 0.1 parts by mass or more and 30 parts by mass with respect to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C) contained in the colored resin composition. or less, more preferably 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 color filter.
  • the colored resin composition of the present invention may contain a polymerization initiation aid (D1).
  • 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 preferably 0.5 parts per 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C) contained in the colored resin composition. It is 1 part by mass or more and 30 parts by mass or less, more preferably 1 part by mass or more and 20 parts by mass or less.
  • 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 (diacetone alcohol), acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone non, cyclohexanone, isophorone, and the like.
  • 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.
  • the solvent (E) is preferably a solvent containing at least one selected from propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, diacetone alcohol and cyclohexanone.
  • 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, more preferably 50% by mass or more and 95% by mass, relative to the total amount of the colored resin composition. % by mass or less, more preferably 70% by mass or more and 95% by mass or less, and even more preferably 75% by mass or more and 90% by mass or less.
  • the total solid content of the colored resin composition is usually 0.01% by mass or more, preferably 1% by mass or more and 60% by mass or less, more preferably 5% by mass or more and 50% by mass or less. , more preferably 5% by mass or more and 30% by mass or less, and still more preferably 10% by mass or more and 25% by mass or less.
  • 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 0.0005% by mass or more and 1% by mass or less, relative to the total amount of the colored resin composition. 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 dispersant described above. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.
  • the colored resin composition if necessary, contains additives known in the art such as fillers, other polymer compounds, adhesion promoters, quenchers, antioxidants, light stabilizers, chain transfer agents, etc. It's okay.
  • the colored resin composition contains a colorant (A), a resin (B), and optionally a polymerizable compound (C), a polymerization initiator (D), a polymerization initiation aid (D1), and a solvent (E). , 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 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 resin (B) may be blended.
  • the coloring agent (A) may be used as a coloring agent-containing liquid obtained by previously dissolving it in part or all of the solvent (E).
  • the desired colored resin composition can be prepared by mixing the colorant-containing liquid thus obtained with the remaining components so as to have a predetermined concentration.
  • a color filter which may be a color conversion layer, can be formed from the colored resin composition of the present invention.
  • a photolithography method, an inkjet method, a printing method, and the like can be used as a method for forming a colored pattern.
  • the photolithographic method is preferred.
  • the photolithographic method is a method in which the colored resin composition is applied to a substrate, dried to form a colored resin composition layer, exposed through a photomask, and developed.
  • a colored coating film which is a cured product of the colored resin 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. It is more preferably 0.5 ⁇ m or more and 6 ⁇ m or less, and still more preferably 0.8 ⁇ m or more and 4.5 ⁇ m or less.
  • 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.
  • 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 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 resin 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 thickness of the colored resin composition layer is not particularly limited, and may be appropriately selected according to the desired thickness of the color filter.
  • the colored resin 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.
  • the exposure apparatus such as a mask aligner and a stepper can be used. is preferably used.
  • 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 contacting the exposed colored resin composition layer with a developer for development.
  • a developer for development By development, the unexposed portion of the colored resin composition layer is dissolved in the developer and removed.
  • the developer for example, aqueous solutions of alkaline compounds such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate and tetramethylammonium hydroxide are preferred.
  • 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 150° C. or higher and 250° C. or lower, more preferably 160° C. or higher and 240° C. or lower.
  • the post-baking time is preferably 1 minute or more and 120 minutes or less, more preferably 10 minutes or more and 60 minutes or less.
  • 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 imaging devices.
  • This reaction solution was stirred for 2 hours while being heated to 110° C. in an oil bath. After allowing the reaction solution to cool, it was filtered through celite to obtain a filtrate. 180 parts of ethyl acetate and 180 parts of ion-exchanged water were added thereto and mixed vigorously, followed by liquid separation to obtain an organic layer. The obtained organic layer was dried with 48 parts of sodium sulfate, and the solid was removed by filtration. The obtained organic layer was concentrated to obtain a crude product.
  • the obtained crude product is purified by silica gel column chromatography (solvent: chloroform/methanol 100/1 to 20/1), the obtained fraction is concentrated under reduced pressure, dried under reduced pressure at 60 ° C., and the formula (BI 11.6 parts of the compound represented by -1) were obtained.
  • This reaction solution was stirred for 2 hours while being heated to 80° C. in an oil bath. After cooling the reaction solution in an ice bath, it was filtered to obtain a solid and a filtrate. Let this solid be crude material A1 and let a filtrate be filtrate A1. The obtained crude product A1 was washed with 50 parts of toluene and then washed twice with 250 parts of ion-exchanged water to obtain a solid. Let this solid be rough body B1. Filtrate A1, 50 parts of toluene, 229 parts of ion-exchanged water and 20.8 parts of 35% hydrochloric acid were put into a bottom-exhausted flask, stirred for 1 hour, and separated to obtain an organic layer.
  • the resulting organic layer was separated and washed with a mixed liquid of 238 parts of ion-exchanged water and 12.5 parts of sodium carbonate, dried with 150 parts of magnesium sulfate, and filtered to remove solids.
  • the obtained organic layer was concentrated to obtain a solid. Let this solid be the crude body C1. Crude B1 and C1 were put into a flask equipped with a stirrer, 4 times mass of acetonitrile was added to the total mass of Crude B1 and C1, and the mixture was stirred for 1 hour. The solid obtained by filtering the mixed solution was washed with 1-fold mass of acetonitrile with respect to the total mass of crude B1 and crude C1. The washed solid was dried at 60° C. under reduced pressure to obtain 75.9 parts of the compound represented by the formula (CI-1). Yield 90.6%.
  • the copolymer (resin B-1) solution having a viscosity of 23 mPas and a solid content of 25.6% as measured by a Brookfield viscometer (23° C.) was maintained at 85° C. for 4 hours, then cooled to room temperature. got The resulting copolymer had a weight average molecular weight Mw of 8.0 ⁇ 10 3 , a dispersity of 2.1, and an acid value converted to solid content of 109 mg-KOH/g.
  • Resin B-1 has the following structural units.
  • the weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured using the GPC method under the following conditions. Apparatus; K2479 (manufactured by Shimadzu Corporation) Column; SHIMADZU Shim-pack GPC-80M Column temperature; 40°C Solvent; Tetrahydrofuran (THF) Test solution concentration; 25 mg/mL (solvent; THF) Flow rate; 1.0 mL/min detector; RI Calibration standard material; TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation) The ratio of the polystyrene-equivalent weight-average molecular weight and the number-average molecular weight obtained above was taken as the dispersity (Mw/Mn).
  • Example 1 ⁇ Preparation of colorant dispersion (A-1) containing compound (I-5a-2)> Compound (I-5a-2) 5 parts, acrylic dispersant 3 parts, resin B-1 (solid content conversion) 2 parts, propylene glycol monomethyl ether acetate 79 parts, diacetone alcohol 10 parts, ethyl lactate 1 part, and 0 300 parts of 0.2 mm zirconia beads were mixed and the resulting mixture was shaken for 1 hour using paint conditioner (LAU). After that, the zirconia beads were removed by filtration to obtain a colorant dispersion (A-1).
  • LiAU paint conditioner
  • Example 2-7 Comparative Examples 1-2
  • Colored resin compositions were obtained in the same manner as in Example 1, except that the compound (I-5a-2) was changed to the following compounds.
  • Example 2 Compound (I-5b)
  • Example 3 Compound (I-4a-2)
  • Example 4 Compound (I-4b)
  • Example 5 Compound (I-9a-2)
  • Example 6 Compound (I-56a-2)
  • Example 7 Compound (I-59a-2) Comparative Example 1: Compound (x1) Comparative Example 2: Compound (x2)
  • the CIE chromaticity coordinates and the stimulus value Y were obtained when the colored resin compositions of Examples 1-7 or Comparative Examples 1-2 and the red resin composition of Preparation Example 1 were mixed at the ratio shown in Table 10.
  • Table 10 shows the values of the stimulus value Y. A larger value of Y indicates a higher brightness.

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Abstract

L'invention a pour objet de fournir un composé permettant de former un filtre coloré d'une excellente brillance. À cet effet, l'invention concerne un composé représenté par la formule (I). (I) [Dans la formule (I), Ｔ1 représente un groupe hydrocarbure aromatique divalent possédant de manière facultative un substituant, Ｔ2 représente un groupe hydrocarbure aromatique divalent possédant de manière facultative un substituant ou un groupe hétérocyclique aromatique divalent possédant de manière facultative un substituant, Ｌ1 représente un groupe hydrocarbure aliphatique de valence a de 1 à 12 atomes de carbone possédant de manière facultative un substituant ou un groupe représenté par la formule (i), et a représente un nombre entier supérieur ou égal à 2.] (i) [Dans la formule (i), Ｔ3 représente un groupe hydrocarbure aromatique de valence a possédant de manière facultative un substituant ou un groupe hétérocyclique aromatique de valence a possédant de manière facultative un substituant, et Ｌ2 représente un groupe hydrocarbure aliphatique divalent de 1 à 5 atomes de carbone possédant de manière facultative un substituant.]
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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014108975A (ja) * 2012-11-30 2014-06-12 Dainippon Printing Co Ltd 色材、色材分散液、カラーフィルター用着色樹脂組成物、カラーフィルター、液晶表示装置及び有機発光表示装置
JP2015034966A (ja) * 2013-07-09 2015-02-19 富士フイルム株式会社 着色組成物、硬化膜、カラーフィルタ、カラーフィルタの製造方法、固体撮像素子、および画像表示装置
JP2016088894A (ja) * 2014-11-06 2016-05-23 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. 化合物
JP2017165808A (ja) * 2016-03-14 2017-09-21 富士フイルム株式会社 着色組成物、硬化膜、カラーフィルタ、カラーフィルタの製造方法、固体撮像素子、画像表示装置および化合物
JP2018003013A (ja) * 2016-06-28 2018-01-11 大日本印刷株式会社 色材分散液、着色樹脂組成物、カラーフィルター、液晶表示装置、及び、発光表示装置
JP2018162364A (ja) * 2017-03-24 2018-10-18 三菱ケミカル株式会社 着色樹脂組成物、カラーフィルタ及び画像表示装置

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014108975A (ja) * 2012-11-30 2014-06-12 Dainippon Printing Co Ltd 色材、色材分散液、カラーフィルター用着色樹脂組成物、カラーフィルター、液晶表示装置及び有機発光表示装置
JP2015034966A (ja) * 2013-07-09 2015-02-19 富士フイルム株式会社 着色組成物、硬化膜、カラーフィルタ、カラーフィルタの製造方法、固体撮像素子、および画像表示装置
JP2016088894A (ja) * 2014-11-06 2016-05-23 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. 化合物
JP2017165808A (ja) * 2016-03-14 2017-09-21 富士フイルム株式会社 着色組成物、硬化膜、カラーフィルタ、カラーフィルタの製造方法、固体撮像素子、画像表示装置および化合物
JP2018003013A (ja) * 2016-06-28 2018-01-11 大日本印刷株式会社 色材分散液、着色樹脂組成物、カラーフィルター、液晶表示装置、及び、発光表示装置
JP2018162364A (ja) * 2017-03-24 2018-10-18 三菱ケミカル株式会社 着色樹脂組成物、カラーフィルタ及び画像表示装置

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