WO2023037996A1 - 着色硬化性組成物 - Google Patents

着色硬化性組成物 Download PDF

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WO2023037996A1
WO2023037996A1 PCT/JP2022/033228 JP2022033228W WO2023037996A1 WO 2023037996 A1 WO2023037996 A1 WO 2023037996A1 JP 2022033228 W JP2022033228 W JP 2022033228W WO 2023037996 A1 WO2023037996 A1 WO 2023037996A1
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group
formula
carbon atoms
hydrocarbon group
optionally substituted
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PCT/JP2022/033228
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English (en)
French (fr)
Japanese (ja)
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智博 中山
拓磨 青木
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住友化学株式会社
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Priority to CN202280060135.XA priority Critical patent/CN117916327A/zh
Priority to KR1020247005200A priority patent/KR20240055731A/ko
Publication of WO2023037996A1 publication Critical patent/WO2023037996A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3415—Five-membered rings
    • C08K5/3417—Five-membered rings condensed with carbocyclic rings
    • 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
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • 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
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
    • C09B47/067—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
    • 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
    • G03F7/004—Photosensitive materials
    • 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
    • G03F7/031—Organic compounds not covered by group G03F7/029

Definitions

  • the present invention relates to a colored curable composition.
  • 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 curable compositions.
  • Colored curable compositions contain various colorants, and for example, colored curable compositions containing an aluminum phthalocyanine compound are known (Patent Documents 1 and 2).
  • the present invention provides a colored curable composition in which the line width change rate of the pattern obtained is small even when the colored curable composition after storage is used, that is, even after storage
  • An object of the present invention is to provide a colored curable composition with good pattern stability.
  • the present invention includes the following inventions.
  • [1] containing a coloring agent, a resin, a polymerizable compound, a polymerization initiator, and a latent antioxidant
  • the coloring agent contains an aluminum phthalocyanine compound
  • the colored curable composition, wherein the polymerization initiator contains an oxime compound.
  • the latent antioxidant is a compound in which the phenolic hydroxyl group of the phenolic antioxidant is protected with a protecting group.
  • the colored curable composition according to [1] or [2], wherein the aluminum phthalocyanine compound is a compound represented by Formula (Xa) or Formula (Xb).
  • R a1 to R a5 and R a13 to R a14 each independently have a hydrogen atom, a hydroxy group, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or a substituent. any two of R a1 and R a2 or R a3 to R a5 may combine with each other to form a ring.
  • X x1 to X x4 each independently represent -R x4 , -OR x4 , -SR x4 , -SO 3 H, -SO 3 - T + , -SO 3 R x10 , -SO 2 NR x11 R x12 , halogen represents an atom or a nitro group.
  • R x4 represents an optionally substituted hydrocarbon group having 1 to 20 carbon atoms, the hydrocarbon group having 2 to 20 carbon atoms and having —CH 2 — In some cases, the --CH 2 -- may be replaced with --O--, --S-- or --CO--.
  • T + represents + N(R X13 ) 4 or an alkali metal ion, and each R X13 independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms.
  • R X10 represents a saturated hydrocarbon group having 1 to 20 carbon atoms.
  • R X11 and R X12 each independently represent a hydrogen atom or an optionally substituted hydrocarbon group having 1 to 20 carbon atoms.
  • nx1 to nx4 each independently represent an integer of 0 to 4;
  • R a6 to R a12 each independently represent a hydrogen atom, a hydroxy group, an optionally substituted hydrocarbon group having 1 to 20 carbon atoms, or an optionally substituted C 1 to represents 20 heterocyclic groups, and R a6 and R a7 , R a8 and R a9 , or R a10 and R a11 may combine with each other to form a ring;
  • the hydrocarbon group has 2 to 20 carbon atoms and has —CH 2 —
  • the —CH 2 — may be replaced with —O—, —S— or —CO—. good.
  • X x5 to X x12 each independently represent -R x5 , -OR x5 , -SR x5 , -SO 3 H, -SO 3 - Q + , -SO 3 R x14 , -SO 2 NR x15 R x16 , halogen represents an atom or a nitro group.
  • R x5 represents an optionally substituted hydrocarbon group having 1 to 20 carbon atoms, the hydrocarbon group having 2 to 20 carbon atoms, and the hydrocarbon group having —CH 2 — In some cases, the --CH 2 -- may be replaced with --O--, --S-- or --CO--.
  • Q + represents + N(R X17 ) 4 or an alkali metal ion
  • each R X17 independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms.
  • R X14 represents a saturated hydrocarbon group having 1 to 20 carbon atoms.
  • R X15 and R X16 each independently represent a hydrogen atom or an optionally substituted hydrocarbon group having 1 to 20 carbon atoms.
  • nx5 to nx12 each independently represent an integer of 0 to 4; ] [4]
  • the compound represented by formula (Xa) is a compound represented by formula (X0) or formula (XI)
  • the compound represented by formula (Xb) is a compound represented by formula (XII)
  • R x1 represents an optionally substituted aliphatic unsaturated hydrocarbon group having 2 to 20 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms
  • R x2 represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 20 carbon atoms, or a single bond connecting Z x2 and R x1 .
  • Z x1 and Z x2 each independently represent a single bond or an oxygen atom.
  • X x1 to X x4 and nx1 to nx4 are the same as above.
  • R x3 represents an optionally substituted C 2-20 aliphatic unsaturated hydrocarbon group or an optionally substituted C 6-20 aromatic hydrocarbon group.
  • Z x3 represents a single bond or an oxygen atom.
  • X x5 to X x12 and nx5 to nx12 are the same as above.
  • [5] The colored curable composition according to [3] or [4], wherein nx1 to nx12 are 0.
  • a display device including the color filter of [6].
  • a solid-state imaging device including the color filter according to [6].
  • the present invention includes a coloring agent (hereinafter sometimes referred to as a coloring agent (A)), a resin (hereinafter sometimes referred to as a resin (B)), a polymerizable compound (hereinafter sometimes referred to as a polymerizable compound (C) ), a polymerization initiator (hereinafter sometimes referred to as a polymerization initiator (D)), and a latent antioxidant (hereinafter sometimes referred to as a latent antioxidant (E)), and the colorant ( A) includes an aluminum phthalocyanine compound, and the polymerization initiator (D) includes an oxime compound.
  • a coloring agent hereinafter sometimes referred to as a coloring agent (A)
  • a resin hereinafter sometimes referred to as a resin (B)
  • a polymerizable compound hereinafter sometimes referred to as a polymerizable compound (C)
  • a polymerization initiator hereinafter sometimes referred to as a polymerization initiator (D)
  • the colored curable composition of the present invention may contain a leveling agent (hereinafter sometimes referred to as leveling agent (F)).
  • the colored curable composition of the present invention may contain a solvent (hereinafter sometimes referred to as solvent (G)).
  • solvent hereinafter sometimes referred to as solvent (G)
  • the compounds exemplified as each component can be used singly or in combination unless otherwise specified.
  • the colored curable composition according to the present invention contains an aluminum phthalocyanine compound as a coloring agent.
  • the aluminum phthalocyanine compound specifically refers to a compound having a phthalocyanine skeleton and forming a complex between the phthalocyanine skeleton and aluminum.
  • the aluminum phthalocyanine compound is preferably a compound represented by formula (Xa) or formula (Xb).
  • formula (Xa) or formula (Xb) the present invention will be described more specifically with partial structures of the compounds represented by Formula (Xa) or Formula (Xb). Definitions common to formula (X0), formula (XI), or formula (XII) will be described later.
  • R a1 to R a5 and R a13 to R a14 each independently have a hydrogen atom, a hydroxy group, an optionally substituted hydrocarbon group having 1 to 20 carbon atoms, or a substituent; any two of R a1 and R a2 or R a3 to R a5 may combine to form a ring.
  • X x1 to X x4 each independently represent -R x4 , -OR x4 , -SR x4 , -SO 3 H, -SO 3 - T + , -SO 3 R x10 , -SO 2 NR x11 R x12 , halogen represents an atom or a nitro group.
  • R x4 represents an optionally substituted hydrocarbon group having 1 to 20 carbon atoms, the hydrocarbon group having 2 to 20 carbon atoms and having —CH 2 — In some cases, the --CH 2 -- may be replaced with --O--, --S-- or --CO--.
  • T + represents + N(R X13 ) 4 or an alkali metal ion, and each R X13 independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms.
  • R X10 represents a saturated hydrocarbon group having 1 to 20 carbon atoms.
  • R X11 and R X12 each independently represent a hydrogen atom or an optionally substituted hydrocarbon group having 1 to 20 carbon atoms.
  • nx1 to nx4 each independently represent an integer of 0 to 4;
  • R a6 to R a12 each independently represent a hydrogen atom, a hydroxy group, an optionally substituted hydrocarbon group having 1 to 20 carbon atoms, or an optionally substituted C 1 to represents 20 heterocyclic groups, and R a6 and R a7 , R a8 and R a9 , or R a10 and R a11 may combine with each other to form a ring;
  • the hydrocarbon group has 2 to 20 carbon atoms and has —CH 2 —
  • the —CH 2 — may be replaced with —O—, —S— or —CO—. good.
  • X x5 to X x12 each independently represent -R x5 , -OR x5 , -SR x5 , -SO 3 H, -SO 3 - Q + , -SO 3 R x14 , -SO 2 NR x15 R x16 , halogen represents an atom or a nitro group.
  • R x5 represents an optionally substituted hydrocarbon group having 1 to 20 carbon atoms, the hydrocarbon group having 2 to 20 carbon atoms, and the hydrocarbon group having —CH 2 — In some cases, the --CH 2 -- may be replaced with --O--, --S-- or --CO--.
  • Q + represents + N(R X17 ) 4 or an alkali metal ion
  • each R X17 independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms.
  • R X14 represents a saturated hydrocarbon group having 1 to 20 carbon atoms.
  • R X15 and R X16 each independently represent a hydrogen atom or an optionally substituted hydrocarbon group having 1 to 20 carbon atoms.
  • nx5 to nx12 each independently represent an integer of 0 to 4; ]
  • R a1 is preferably -R b1 , -OR b1 , -SR b1 or -CO-R b1 .
  • R a2 is preferably -R b2 , -OR b2 , -SR b2 or -CO-R b2 .
  • R b1 and R b2 represent optionally substituted hydrocarbon groups having 1 to 20 carbon atoms, and R b1 and R b2 may combine with each other to form a ring.
  • R a12 is preferably -R b3 , -OR b3 , -SR b3 or -CO-R b3 .
  • R b3 represents an optionally substituted hydrocarbon group having 1 to 20 carbon atoms.
  • the compound represented by formula (Xa) is preferably a compound represented by formula (X0) or formula (XI).
  • the compound represented by the formula (Xb) is preferably a compound represented by the formula (XII).
  • the present invention will be described more specifically with partial structures of the compounds represented by formula (X0), formula (XI), or formula (XII).
  • R x1 represents an optionally substituted aliphatic unsaturated hydrocarbon group having 2 to 20 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms
  • R x2 represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 20 carbon atoms, or a single bond connecting Z x2 and R x1 .
  • Z x1 and Z x2 each independently represent a single bond or an oxygen atom.
  • X x1 to X x4 and nx1 to nx4 are the same as above.
  • R x3 represents an optionally substituted C 2-20 aliphatic unsaturated hydrocarbon group or an optionally substituted C 6-20 aromatic hydrocarbon group.
  • Z x3 represents a single bond or an oxygen atom.
  • X x5 to X x12 and nx5 to nx12 are the same as above. ]
  • the aluminum phthalocyanine compound is also preferably a compound represented by formula (YI) or formula (YII).
  • YI formula represented by formula (YI) or formula (YII).
  • the present invention will be described more specifically with partial structures of the compounds represented by formula (YI) or formula (YII).
  • R y1 represents a hydrogen atom or an optionally substituted hydrocarbon group having 1 to 20 carbon atoms.
  • R y2 represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 20 carbon atoms, or a single bond connecting Z y3 and R y1 .
  • Y 1 and Z y1 each independently represent an oxygen atom or a sulfur atom.
  • Zy2 and Zy3 each independently represent a single bond, an oxygen atom or a sulfur atom. However, at least one of Y1 , Zy1 , Zy2 and Zy3 represents a sulfur atom.
  • X y1 to X y4 each independently represent -R y4 , -OR y4 , -SR y4 , -SO 3 H, -SO 3 - M + , -SO 3 R y10 , -SO 2 NR y11 R y12 , halogen represents an atom or a nitro group.
  • R y4 represents an optionally substituted hydrocarbon group having 1 to 20 carbon atoms.
  • M + represents + N(R y13 ) 4 or an alkali metal ion, and each R y13 independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms.
  • R y10 represents a saturated hydrocarbon group having 1 to 20 carbon atoms.
  • R y11 and R y12 each independently represent a hydrogen atom or an optionally substituted hydrocarbon group having 1 to 20 carbon atoms.
  • ny1 to ny4 each independently represent an integer of 0 to 4;
  • R y3 represents a hydrogen atom or an optionally substituted hydrocarbon group having 1 to 20 carbon atoms.
  • Y2 and Zy4 each independently represent an oxygen atom or a sulfur atom.
  • Zy5 represents a single bond, an oxygen atom or a sulfur atom. However, at least one of Y2 , Zy4 and Zy5 represents a sulfur atom.
  • X y5 to X y12 are each independently -R y5 , -OR y5 , -SR y5 , -SO 3 H, -SO 3 - W + , -SO 3 R y14 , -SO 2 NR y15 R y16 , halogen represents an atom or a nitro group.
  • R y5 represents an optionally substituted hydrocarbon group having 1 to 20 carbon atoms.
  • W + represents + N(R y17 ) 4 or an alkali metal ion, and each R y17 independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms.
  • R y14 represents a saturated hydrocarbon group having 1 to 20 carbon atoms.
  • R y15 and R y16 each independently represent a hydrogen atom or an optionally substituted hydrocarbon group having 1 to 20 carbon atoms.
  • ny5 to ny12 each independently represent an integer of 0 to 4; ]
  • the compound represented by formula (YI) includes a compound having a resonance structure represented by formula (YIa) or a compound represented by formula (YIb) in equilibrium, and formula (YII)
  • the compound represented by includes a compound having a resonance structure represented by formula (YIIa) or a compound represented by formula (YIIb) having an equilibrium relationship.
  • R y1 , R y2 , Y 1 , Z y1 , Z y2 , Z y3 , X y1 to X y4 and ny1 to ny4 are the same as above.
  • R y3 , Y 2 , Z y4 , Z y5 , X y5 to X y12 and ny5 to ny12 are the same as above.
  • the aliphatic unsaturated hydrocarbon group represented by R x1 and R x3 has 2 to 20 carbon atoms, more preferably 2 to 10 carbon atoms, still more preferably 2 to 7 carbon atoms, and particularly preferably 2 to 5.
  • the aliphatic unsaturated hydrocarbon groups represented by R x1 and R x3 may be chain or cyclic (alicyclic hydrocarbon groups).
  • the unsaturated chain hydrocarbon groups represented by R x1 and R x3 may be linear or branched, and specifically: Ethenyl group (vinyl group), propenyl group (e.g., 1-propenyl group, 2-propenyl group (allyl group)), 1-methylethenyl group, butenyl group (e.g., 1-butenyl group, 2-butenyl group, 3-butenyl group), 3-methyl-1-butenyl group, 1-methyl-1-butenyl group, 3-methyl-2-butenyl group, 1,3-butadienyl group, 3-methyl-1,2-butadienyl group, 1- (2-propenyl) ethenyl group, 1-(1-methylethenyl) ethenyl group, 1,1-dimethyl-2-propenyl group, 1,2-dimethyl-1-propenyl group, 1-ethyl-2-propenyl group, pentenyl group (e.g., 1-pen
  • Examples of unsaturated alicyclic hydrocarbon groups represented by R x1 and R x3 include: Cycloalkenyl groups such as cyclohexenyl group (e.g., cyclohex-1-en-1-yl group, cyclohex-2-en-1-yl group, cyclohex-3-en-1-yl group), cycloheptenyl group and cyclooctenyl group ; unsaturated polycyclic hydrocarbon groups such as norbornenyl groups; etc.
  • Cycloalkenyl groups such as cyclohexenyl group (e.g., cyclohex-1-en-1-yl group, cyclohex-2-en-1-yl group, cyclohex-3-en-1-yl group), cycloheptenyl group and cyclooctenyl group ; unsaturated polycyclic hydrocarbon groups such as norbornenyl groups; etc.
  • the aliphatic unsaturated hydrocarbon groups having 2 to 20 carbon atoms represented by R x1 and R x3 may have a substituent.
  • Substituents for the aliphatic unsaturated hydrocarbon groups having 2 to 20 carbon atoms represented by R x1 and R x3 include aromatic hydrocarbon groups having 6 to 20 carbon atoms which may be substituted, substituted a heterocyclic group optionally having a group, a halogen atom, a nitro group, a cyano group, —OR xa1 , —CO 2 R xa1 , —SR xa1 , —SO 3 R xa1 , —SO 2 NR xa1 R xa2 and — NR xa1 R xa2 and the like.
  • R xa1 and R xa2 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms.
  • the hydrocarbon groups having 1 to 20 carbon atoms represented by R xa1 and R xa2 are 1 carbon atoms represented by R b1 to R b3 , R x2 , R x4 , R x5 and R y1 to R y5 described later. ⁇ 20 hydrocarbon groups.
  • the aliphatic unsaturated hydrocarbon group has an aromatic hydrocarbon group as a substituent
  • the total carbon number of the aliphatic unsaturated hydrocarbon group and the aromatic hydrocarbon group as a substituent is 20. It is preferable that:
  • the aromatic hydrocarbon group having 6 to 20 carbon atoms used as a substituent for the unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms represented by R x1 and R x3 includes: phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2-ethylphenyl group, 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, 4-vinylphenyl group, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group,
  • the aromatic hydrocarbon group preferably has 6 to 10 carbon atoms, more preferably 6 to 8 carbon atoms.
  • the aromatic hydrocarbon group may have a substituent, and examples of the substituent include a halogen atom, a nitro group, a cyano group, —OR xa1 , —CO 2 R xa1 , —SR xa1 and —SO 3 R xa1 . , —SO 2 NR xa1 R xa2 and —NR xa1 R xa2 (provided that R xa1 and R xa2 are the same as above).
  • the heterocyclic group used as a substituent of the unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms represented by R x1 and R x3 may be monocyclic or polycyclic, preferably is a heterocyclic ring containing a heteroatom as a ring member. Heteroatoms include nitrogen, oxygen and sulfur atoms.
  • Heterocyclic rings containing only nitrogen atoms as heteroatoms include monocyclic saturated heterocyclic rings such as aziridine, azetidine, pyrrolidine, piperidine and piperazine; pyrrole, pyrazole, imidazole, 1,2,3-triazole, 1,2,4 - Monocyclic unsaturated heterocycles such as 5-membered unsaturated heterocycles such as triazole, 6-membered unsaturated heterocycles such as pyridine, pyridazine, pyrimidine, pyrazine, 1,3,5-triazine; Condensed bicyclic rings such as indoline, isoindoline, isoindoline-1,3-dione, indole, indolizine, benzimidazole, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazo
  • heterocycles condensed tricyclic heterocycles such as carbazole, acridine, and phenazine;
  • Heterocyclic rings containing only oxygen atoms as heteroatoms include monocyclic saturated heterocyclic rings such as oxirane, oxetane, tetrahydrofuran, tetrahydropyran, 1,3-dioxane and 1,4-dioxane; 1,4-dioxaspiro [4.
  • Bicyclic saturated heterocycles such as decane and 1,4-dioxaspiro[4.5]nonane; Lactone heterocycles such as ⁇ -acetolactone, ⁇ -propiolactone, ⁇ -butyrolactone and ⁇ -valerolactone; monocyclic unsaturated heterocycles such as 5-membered unsaturated heterocyclic rings such as furan, 2H-pyran, 6-membered unsaturated heterocyclic rings such as 4H-pyran; 1-benzofuran, benzopyran, benzodioxole, condensed bicyclic heterocycles such as chroman and isochroman; condensed tricyclic heterocycles such as xanthene and dibenzofuran; and the like.
  • Lactone heterocycles such as ⁇ -acetolactone, ⁇ -propiolactone, ⁇ -butyrolactone and ⁇ -valerolactone
  • monocyclic unsaturated heterocycles such as 5-membered unsaturated
  • the heterocyclic ring containing only a sulfur atom as a heteroatom includes a 5-membered saturated heterocyclic ring such as dithiolane, a monocyclic saturated heterocyclic ring such as a 6-membered saturated heterocyclic ring such as thiane and 1,3-dithiane; monocyclic unsaturated heterocycles such as 5-membered unsaturated heterocycles such as 4H-thiopyran; benzothiopyrans such as benzotetrahydrothiopyran; condensed bicyclic systems such as benzothiophene heterocycles; condensed tricyclic heterocycles such as thianthrene and dibenzothiophene; Heterocyclic rings containing a nitrogen atom and an oxygen atom as heteroatoms include monocyclic saturated heterocyclic rings such as morpholine, 2-pyrrolidone and 2-piperidone; monocyclic unsaturated heterocyclic rings such as oxazole and isoxazole; Condensed bicyclic
  • Heterocyclic rings containing a nitrogen atom and a sulfur atom as heteroatoms include monocyclic unsaturated heterocyclic rings such as thiazole; condensed bicyclic heterocyclic rings such as benzothiazole; condensed tricyclic heterocyclic rings such as phenothiazine; be done.
  • the heterocyclic group preferably has 2 to 30 carbon atoms, more preferably 3 to 22 carbon atoms, and still more preferably 3 to 20 carbon atoms.
  • the heterocyclic group may have a substituent, and examples of the substituent include a halogen atom, a nitro group, a cyano group, —OR xa1 , —CO 2 R xa1 , —SR xa1 , —SO 3 R xa1 , — SO 2 NR xa1 R xa2 and -NR xa1 R xa2 (provided that R xa1 and R xa2 are the same as above).
  • the bonding position of the heterocyclic ring is a portion from which any hydrogen atom contained in each ring is eliminated.
  • Halogen atoms used as substituents of the aliphatic unsaturated hydrocarbon groups having 2 to 20 carbon atoms represented by R x1 and R x3 are exemplified by fluorine, chlorine, bromine and iodine atoms.
  • the aromatic hydrocarbon group represented by R x1 and R x3 has 6 to 20 carbon atoms, preferably 6 to 10 carbon atoms, still more preferably 6 to 8 carbon atoms, and particularly preferably 6 carbon atoms.
  • the aromatic hydrocarbon group represented by R x1 and R x3 includes 6 to 20 carbon atoms used as substituents for the aliphatic unsaturated hydrocarbon groups of 2 to 20 carbon atoms represented by R x1 and R x3 . and the aromatic hydrocarbon groups exemplified as the aromatic hydrocarbon groups of .
  • the aromatic hydrocarbon groups having 6 to 20 carbon atoms represented by R x1 and R x3 may have a substituent.
  • substituents of the aromatic hydrocarbon group having 6 to 20 carbon atoms represented by R x1 and R x3 include halogen atoms such as fluorine, chlorine, bromine and iodine atoms, nitro group, cyano group, -OR xa1 , —CO 2 R xa1 , —SR xa1 , —SO 3 R xa1 , —SO 2 NR xa1 R xa2 and —NR xa1 R xa2 (provided that R xa1 and R xa2 are the same as above).
  • the number of carbon atoms in the hydrocarbon group represented by is 1 to 20, preferably 1 to 15.
  • the hydrocarbon group having 1 to 20 carbon atoms represented by may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, and the aliphatic hydrocarbon group is saturated or unsaturated. may be linear or cyclic (alicyclic hydrocarbon group).
  • the saturated or unsaturated chain hydrocarbon group represented by 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, n-decyl group, n-undecyl group , n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group,
  • alkyl group shaped alkyl group; isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, 2-ethylbutyl group, 3,3-dimethylbutyl group, 1,1,3,3-tetramethylbutyl group, 1-methylbutyl group, 1-ethyl propyl group, 3-methylbutyl group, neopentyl group, 1,1-dimethylpropyl group, 1,1,2-trimethylpropyl group, 2-methylpentyl group, 3-ethylpentyl group, 1,3-dimethylbutyl group, 2 -propylpentyl group, 1-ethyl-1,2-dimethylpropyl group, 1-methylpentyl group, 4-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, 2-ethylhexyl group, 1-methylhexyl group, 1-ethylpentyl group, 1-propyl
  • the number of carbon atoms in the saturated chain hydrocarbon group represented by is preferably 1 to 10, more preferably 1 to 7, and still more preferably 1 to 5.
  • the number of carbon atoms in the unsaturated chain hydrocarbon group represented by is preferably 2 to 10, more preferably 2 to 7, and still more preferably 2 to 5.
  • saturated or unsaturated alicyclic hydrocarbon group represented by cyclopropyl group, 1-methylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1, 2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4-dimethylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,
  • the number of carbon atoms in the saturated or unsaturated alicyclic hydrocarbon group represented by is preferably 3-10.
  • the aromatic hydrocarbon group represented by is an aromatic hydrocarbon having 6 to 20 carbon atoms used as a substituent for the aliphatic unsaturated hydrocarbon groups having 2 to 20 carbon atoms represented by R x1 and R x3 Examples of the group include the aromatic hydrocarbon groups exemplified.
  • the number of carbon atoms in the aromatic hydrocarbon group represented by is preferably 6-20, more preferably 6-10, still more preferably 6-8.
  • the hydrocarbon group represented by is a combination of the above-listed hydrocarbon groups (e.g., an aromatic hydrocarbon group and at least one of an aromatic hydrocarbon group, a chain hydrocarbon group and an alicyclic hydrocarbon group) may be a base, benzyl group, (2-methylphenyl) methyl group, (3-methylphenyl) methyl group, (4-methylphenyl) methyl group, (2-ethylphenyl) methyl group, (3-ethylphenyl) methyl group, (4 -ethylphenyl)methyl group, (2-(tert-butyl)phenyl)methyl group, (3-(tert-butyl)phenyl)methyl group, (3-(tert-butyl)phenyl)methyl group, (3-(tert-butyl)phenyl)methyl group, (3-(tert-butyl)phenyl)methyl group, (3-(tert-butyl)phenyl)methyl group, (3-(tert-butyl
  • the group represented by is a combination of the above-mentioned hydrocarbon groups (e.g., a chain hydrocarbon group and an alicyclic hydrocarbon group), such as a cyclopropylmethyl group, a cyclopropylethyl group, a cyclobutylmethyl cyclobutylethyl group, cyclopentylmethyl group, cyclopentylethyl group, cyclohexylmethyl group, (2-methylcyclohexyl)methyl group, cyclohexylethyl group, adamantylmethyl group, etc. It may be an alkyl group.
  • R x4 and R x5 When the hydrocarbon group represented by R a1 to R a14 , R x4 and R x5 has 2 to 20 carbon atoms and the hydrocarbon group has —CH 2 —, the —CH 2 — is —O -, -S- or -CO- may be substituted. However, in the hydrocarbon group having 2 to 20 carbon atoms, adjacent —CH 2 — are not simultaneously substituted with —O— and/or —S—, and the terminal —CH 2 — is —O—, -S- or -CO- is never substituted.
  • a plurality of —CH 2 — substitutable hydrocarbon groups having 1 to 20 carbon atoms exist, the number of substitutions is not necessarily limited to one.
  • two —CH 2 — in a hydrocarbon group having 4 carbon atoms are replaced with —O— to give *—O—CH 2 —O—
  • a group in which -CH 2 - in a hydrocarbon group having 1 to 20 carbon atoms which may be substituted with -O-, -S- or -CO-.
  • the hydrocarbon group having 1 to 20 carbon atoms represented by may have a substituent.
  • Substituents for the hydrocarbon group having 1 to 20 carbon atoms represented by may be optionally substituted heterocyclic groups, halogen atoms, nitro groups, cyano groups, —OR xa1 , —CO 2 R xa1 , -SR xa1 , -SO 3 R xa1 , -SO 2 NR xa1 R xa2 and -NR xa1 R xa2 (provided that R xa1 and R xa2 are the same as above).
  • the heterocyclic group used as a substituent of the hydrocarbon group having 1 to 20 carbon atoms represented by may be monocyclic or polycyclic, preferably a heteroatom as a ring constituent is a heterocyclic ring containing Heteroatoms include nitrogen, oxygen and sulfur atoms.
  • heterocyclic ring examples include the same heterocyclic groups used as substituents of aliphatic unsaturated hydrocarbon groups having 2 to 20 carbon atoms represented by R x1 and R x3 .
  • the heterocyclic group preferably has 2 to 30 carbon atoms, more preferably 3 to 22 carbon atoms, and still more preferably 3 to 20 carbon atoms.
  • the heterocyclic group may have a substituent, and examples of the substituent include a halogen atom, a nitro group, a cyano group, —OR xa1 , —CO 2 R xa1 , —SR xa1 , —SO 3 R xa1 , — SO 2 NR xa1 R xa2 and -NR xa1 R xa2 (provided that R xa1 and R xa2 are the same as above).
  • the bonding position of the heterocyclic ring is a portion from which any hydrogen atom contained in each ring is eliminated.
  • halogen atom used as a substituent of the hydrocarbon group having 1 to 20 carbon atoms represented by is exemplified by a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • the saturated hydrocarbon groups having 1 to 20 carbon atoms represented by R x10 , R x14 , R y10 and X y14 include R a1 to R a14 , R b1 to R b3 , R x2 , R x4 , R x5 , R Of the hydrocarbon groups represented by x11 to R x13 , R x15 to R x17 , R y1 to R y5 , R y11 to R y13 and R y15 to R y17 , straight-chain alkyl groups and branched-chain alkyl groups , the cycloalkyl group, and the groups exemplified as the saturated polycyclic hydrocarbon group.
  • the heterocyclic group having 1 to 20 carbon atoms represented by R a1 to R a14 may be monocyclic or polycyclic, and is preferably a heterocyclic ring containing a heteroatom as a ring constituent. be. Heteroatoms include nitrogen, oxygen and sulfur atoms. Examples of the heterocyclic ring include the same heterocyclic groups used as substituents of aliphatic unsaturated hydrocarbon groups having 2 to 20 carbon atoms represented by R x1 and R x3 . The heterocyclic group preferably has 3 to 20 carbon atoms.
  • the heterocyclic group may have a substituent, and examples of the substituent include a halogen atom, a nitro group, a cyano group, an alkyl group having 1 to 10 carbon atoms, —OR xa1 , —CO 2 R xa1 and —SR. xa1 , -SO 3 R xa1 , -SO 2 NR xa1 R xa2 and -NR xa1 R xa2 (provided that R xa1 and R xa2 are the same as above).
  • the bonding position of the heterocyclic ring is a portion from which any hydrogen atom contained in each ring is eliminated.
  • R x1 is an optionally substituted aliphatic unsaturated hydrocarbon group having 2 to 20 carbon atoms
  • an unsaturated bond may be formed between the carbon atoms that are members of the ring, and is a member of the ring
  • An unsaturated bond may be formed between a carbon atom and a carbon atom that is not a member of the ring, and an unsaturated bond may be formed between carbon atoms that are not a member of the ring.
  • R y2 is a single bond connecting Z y3 and R y1
  • a ring is formed. That is, when R y2 is a single bond connecting Z y3 and R y1 , any carbon atom in the optionally substituted hydrocarbon group having 1 to 20 carbon atoms represented by R y1 A bond formed by sharing a pair of electrons with Z y3 corresponds to a single bond represented by R y2 .
  • nx1 to nx12 and ny1 to ny12 each independently represent an integer of 0 to 4; nx1 to nx4 may be the same or different, but are preferably the same; nx5 to nx12 may be the same or different, but are preferably the same; ny4 may be the same or different but is preferably the same, and ny5 to ny12 may be the same or different but are preferably the same.
  • nx1 represents an integer of 2 or more
  • multiple X x1 may be the same or different. The same applies to a plurality of X x2 to X x12 and X y1 to X y12 when nx2 to nx12 and ny1 to ny12 represent integers of 2 or more.
  • substitution position of X x1 is not particularly limited, but when nx1 is 1, it is preferably at the 2nd or 3rd position in the following partial structural formula, position is preferred. The same applies to the substitution positions of X x2 to X x12 and X y1 to X y12 .
  • * indicates a bond.
  • halogen atoms represented by X x1 to X x12 and X y1 to X y12 include fluorine, chlorine, bromine and iodine atoms, preferably fluorine.
  • -R x4 represented by X x1 to X x4 , -R x5 represented by X x5 to X x12 , -R y4 represented by X y1 to X y4 or -R represented by X y5 to X y12 y5 is preferably an aliphatic hydrocarbon group having 1 to 20 carbon atoms, more preferably a saturated chain hydrocarbon group having 1 to 20 carbon atoms, still more preferably a saturated chain hydrocarbon group having 1 to 10 carbon atoms, A branched alkyl group having a number of 1 to 5 is more preferred, and a tert-butyl group is particularly preferred.
  • R X13 , R X17 , R y13 and R y17 are each independently preferably a hydrogen atom or a saturated chain hydrocarbon group having 1 to 20 carbon atoms, and a hydrogen atom or a saturated chain hydrocarbon group having 1 to 10 carbon atoms. is more preferred, and a hydrogen atom or a saturated chain hydrocarbon group having 1 to 5 carbon atoms is even more preferred.
  • Alkali metal ions represented by T + , Q + , M + , and W + are each independently preferably lithium ion, sodium ion, or potassium ion.
  • the saturated hydrocarbon group having 1 to 20 carbon atoms represented by R x10 , R x14 , R y10 and R y14 is preferably a linear or branched alkyl group having 1 to 20 carbon atoms. ⁇ 10 linear alkyl groups are more preferred.
  • R x11 , R x12 , R x15 , R x16 , R y11 , R y12 , R y15 and R y16 are each independently preferably a hydrogen atom or a saturated chain hydrocarbon group having 1 to 20 carbon atoms, and a hydrogen atom Alternatively, a saturated chain hydrocarbon group having 1 to 10 carbon atoms is more preferable, and a hydrogen atom or a saturated chain hydrocarbon group having 1 to 5 carbon atoms is more preferable.
  • R x1 is An optionally substituted unsaturated chain hydrocarbon group having 2 to 20 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 10 carbon atoms is preferred, An optionally substituted unsaturated chain hydrocarbon group having 2 to 10 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 8 carbon atoms is more preferable, An optionally substituted unsaturated chain hydrocarbon group having 2 to 7 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 7 carbon atoms is more preferable, optionally substituted ethenyl group, optionally substituted propenyl group, optionally substituted butenyl group, optionally substituted 3-methyl-2 -butenyl group, optionally substituted 3-methyl-1,2-butadienyl group, optionally substituted heptenyl group, optionally substituted ethynyl group, substituent A propynyl group optionally having , a butynyl group optionally having a substitu
  • Rx1 When the aliphatic unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by R x1 has a substituent, the substituent is preferably a phenyl group.
  • Rx2 is An optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms or an optionally substituted aliphatic unsaturated hydrocarbon group having 2 to 20 carbon atoms is preferred.
  • examples of the aliphatic unsaturated hydrocarbon group having 2 to 20 carbon atoms include the groups described above as the alkenyl group, alkynyl group and unsaturated alicyclic hydrocarbon group.
  • substituents that the C2-C20 aliphatic unsaturated hydrocarbon group may have include C2-C20 aliphatic unsaturated hydrocarbon groups represented by R x1 and R x3 .
  • the groups described as the optional substituents can be mentioned.
  • the total carbon number of the aliphatic unsaturated hydrocarbon group and the aromatic hydrocarbon group as a substituent is 20. It is below.
  • Specific examples of the aliphatic unsaturated hydrocarbon group having an aromatic hydrocarbon group as a substituent include groups exemplified as arylalkenyl groups and arylalkynyl groups.
  • R x2 is An optionally substituted aromatic hydrocarbon group having 6 to 10 carbon atoms or an unsaturated chain hydrocarbon group having 2 to 20 carbon atoms which may have a substituent (i.e. alkenyl group, alkynyl group) is more preferred, An optionally substituted aromatic hydrocarbon group having 6 to 8 carbon atoms or an optionally substituted unsaturated chain hydrocarbon group having 2 to 7 carbon atoms is more preferable, phenyl group optionally having substituent(s), ethenyl group optionally having substituent(s), propenyl group optionally having substituent(s), butenyl group optionally having substituent(s), substituent 3-methyl-2-butenyl group optionally having a substituent, 3-methyl-1,2-butadienyl group optionally having a substituent, a heptenyl group optionally having a substituent, a substituent An optionally substituted ethynyl group, an optionally substituted propynyl group,
  • the substituent is preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms, more preferably a phenyl group.
  • X x1 to X x4 are each independently preferably —R x4 or a halogen atom, more preferably a linear or branched alkyl group having 1 to 10 carbon atoms, or a halogen atom, and 1 to 5 carbon atoms. is more preferred, and a tert-butyl group, a fluorine atom, a chlorine atom, or a bromine atom is particularly preferred.
  • nx1 to nx4 are each independently, for example, 0 to 2 or 4, preferably 0 to 2, more preferably 0 to 1, still more preferably 0.
  • R x3 is An optionally substituted unsaturated chain hydrocarbon group having 2 to 20 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 10 carbon atoms is preferred, An optionally substituted unsaturated chain hydrocarbon group having 2 to 10 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 8 carbon atoms is more preferable, An optionally substituted unsaturated chain hydrocarbon group having 2 to 5 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 7 carbon atoms is more preferable, optionally substituted ethenyl group, optionally substituted propenyl group, optionally substituted butenyl group, optionally substituted ethynyl group, substituent A propynyl group optionally having , a butynyl group optionally having a substituent, or a phenyl group optionally having a substituent are particularly preferable.
  • the substituent is preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms, more preferably a phenyl group.
  • X x5 to X x12 are each independently preferably —R x5 or a halogen atom, more preferably a linear or branched alkyl group having 1 to 10 carbon atoms, or a halogen atom, and 1 to 5 carbon atoms. is more preferred, and a tert-butyl group, a fluorine atom, a chlorine atom, or a bromine atom is particularly preferred.
  • nx5 to nx12 are each independently, for example, 0 to 2 or 4, preferably 0 to 2, more preferably 0 to 1, still more preferably 0.
  • R x1 , R x2 , Z x1 and Z x2 are the same as above. ]
  • Examples of compounds represented by formula (XIA) include compounds represented by formulas (XIA-1) to (XIA-190) shown in Tables 1 to 4.
  • Examples of compounds represented by formula (XIB) include compounds represented by formulas (XIB-1) to (XIB-190) shown in Tables 5 to 8.
  • Examples of compounds represented by formula (XIC) include compounds represented by formulas (XIC-1) to (XIC-190) shown in Tables 9 to 12.
  • Examples of compounds represented by formula (XID) include compounds represented by formulas (XID-1) to (XID-190) shown in Tables 13 to 16.
  • Examples of compounds represented by formula (XIE) include compounds represented by formulas (XIE-1) to (XIE-190) shown in Tables 17 to 20.
  • R x6 and R x7 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent
  • Examples of the hydrocarbon group having 1 to 20 carbon atoms which may have a substituent include substituents represented by R b1 to R b3 , R x2 , R x4 , R x5 and R y1 to R y5 .
  • R x6 and R x7 are each independently preferably a hydrogen atom or a linear or branched alkyl group having 1 to 10 carbon atoms. * represents a bond.
  • Formula (XIA-1) ⁇ Formula (XIA-12), Formula (XIA-91) ⁇ Formula (XIA-102), Formula (XIA-103) ⁇ Formula (XIA-108), Formula (XIA-115) ⁇ Formula (XIA-119), Formula (XIA-126) ⁇ Formula (XIA-129), Formula (XIA-136) ⁇ Formula (XIA-138), Formula (XIA-145) ⁇ Formula (XIA-146), Formula ( XIA-153), compounds represented by formulas (XIA-181) to (XIA-190) are preferred, Formula (XIA-1) ⁇ Formula (XIA-12), Formula (XIA-103) ⁇ Formula (XIA-105), Formula (XIA-115) ⁇ Formula (XIA-116), Formula (XIA-126), Formula (XIA-136) ⁇ formula (XIA-138), formula (XIA-145) ⁇ formula (XIA-146), formula (
  • Formula (XIC-1) As the compound represented by the formula (XIC), Formula (XIC-1) ⁇ Formula (XIC-12), Formula (XIC-91) ⁇ Formula (XIC-102), Formula (XIC-103) ⁇ Formula (XIC-108), Formula (XIC-115) ⁇ Formula (XIC-119), Formula (XIC-126) ⁇ Formula (XIC-129), Formula (XIC-136) ⁇ Formula (XIC-138), Formula (XIC-145) ⁇ Formula (XIC-146), Formula ( XIC-153), compounds represented by formulas (XIC-181) to (XIC-190) are preferred, Formula (XIC-1) ⁇ Formula (XIC-12), Formula (XIC-103) ⁇ Formula (XIC-105), Formula (XIC-115) ⁇ Formula (XIC-116), Formula (XIC-126) is more preferred, Compounds represented by formula (XIC-1) and formula (XIC-115) are more preferred.
  • Formula (XIE-1) As the compound represented by the formula (XIE), Formula (XIE-1) ⁇ Formula (XIE-12), Formula (XIE-91) ⁇ Formula (XIE-102), Formula (XIE-103) ⁇ Formula (XIE-108), Formula (XIE-115) ⁇ Formula (XIE-119), Formula (XIE-126) ⁇ Formula (XIE-129), Formula (XIE-136) ⁇ Formula (XIE-138), Formula (XIE-145) ⁇ Formula (XIE-146), Formula ( XIE-153), compounds represented by formulas (XIE-181) to (XIE-190) are preferred, Formula (XIE-1) ⁇ Formula (XIE-12), Formula (XIE-103) ⁇ Formula (XIE-105), Formula (XIE-115) ⁇ Formula (XIE-116), Formula (XIE-126) is more preferred, Compounds represented by Formula (XIE-1) and Formula (XIE-115) are more preferred.
  • Examples of compounds represented by formula (XIIA) include compounds represented by formulas (XIIA-1) to (XIIA-18) shown in Table 21.
  • Examples of compounds represented by formula (XIIB) include compounds represented by formulas (XIIB-1) to (XIIB-18) shown in Table 22.
  • Examples of compounds represented by formula (XIIC) include compounds represented by formulas (XIIC-1) to (XIIC-18) shown in Table 23.
  • Examples of compounds represented by formula (XIID) include compounds represented by formulas (XIID-1) to (XIID-18) shown in Table 24.
  • Examples of compounds represented by formula (XIIE) include compounds represented by formulas (XIIE-1) to (XIIE-18) shown in Table 25.
  • the symbols described in the “R x3 ” columns in Tables 21 to 25 correspond to groups represented by formulas (xiii-1) to (xiii-9). * represents a bond.
  • the compound represented by formula (X0) can be produced, for example, by appropriately reacting the compound represented by formula (XIII) with concentrated sulfuric acid.
  • a compound represented by formula (XI) can be produced, for example, by appropriately reacting a compound represented by formula (XIII) with a compound represented by formula (XIV).
  • the compound represented by formula (XII) can be obtained, for example, by appropriately reacting a compound represented by formula (XIIIa), a compound represented by formula (XIIIb), and a compound represented by formula (XV).
  • R x1 , R x2 , Z x1 , Z x2 , X x1 to X x4 and nx1 to nx4 are the same as above.
  • R y1 is An aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent is preferred, more preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, more preferably an aromatic hydrocarbon group having 6 to 8 carbon atoms which may have a substituent, An optionally substituted phenyl group is particularly preferred.
  • Ry2 is An optionally substituted aliphatic unsaturated hydrocarbon group having 2 to 20 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms is preferred.
  • the aliphatic unsaturated hydrocarbon group having 2 to 20 carbon atoms in preferred embodiments of R y2 and R y3 described later includes the groups described as the alkenyl group, alkynyl group, and unsaturated alicyclic hydrocarbon group described above. is mentioned.
  • substituents that the unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms may have include unsaturated aliphatic hydrocarbon groups having 2 to 20 carbon atoms represented by R x1 and R x3 .
  • the groups described as the optional substituents can be mentioned.
  • the total carbon number of the aliphatic unsaturated hydrocarbon group and the aromatic hydrocarbon group as a substituent is 20. It is below.
  • Specific examples of the aliphatic unsaturated hydrocarbon group having an aromatic hydrocarbon group as a substituent include groups exemplified as arylalkenyl groups and arylalkynyl groups.
  • R y2 is Unsaturated chain hydrocarbon groups of 2 to 10 carbon atoms which may have substituents (that is, alkenyl groups and alkynyl groups) or aromatic carbon atoms of 6 to 10 carbon atoms which may have substituents more preferably a hydrogen group
  • substituents that is, alkenyl groups and alkynyl groups
  • aromatic carbon atoms of 6 to 10 carbon atoms which may have substituents more preferably a hydrogen group
  • An optionally substituted unsaturated chain hydrocarbon group having 2 to 7 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 8 carbon atoms is more preferable
  • An optionally substituted alkenyl group having 2 to 7 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 8 carbon atoms is more preferable
  • An optionally substituted ethenyl group or an optionally substituted phenyl group is particularly preferred.
  • ny1 to ny4 are each independently, for example, 0 to 2 or 4, preferably 0 to 2, more preferably 0 to 1, still more preferably 0.
  • X y1 to X y4 are each independently preferably -R y4 or a halogen atom, more preferably a linear or branched alkyl group having 1 to 10 carbon atoms, or a halogen atom, and 1 to 5 carbon atoms. is more preferred, and a tert-butyl group, a fluorine atom, a chlorine atom, or a bromine atom is particularly preferred.
  • At least one of Y 1 , Z y1 , Z y2 and Z y3 represents a sulfur atom, Y 1 is a sulfur atom and Z y1 is an oxygen atom, Y 1 is an oxygen atom and Z y1 is a sulfur atom and Z y2 and Z y3 are sulfur atoms.
  • Zy2 and Zy3 are preferably single bonds.
  • Ry3 is An optionally substituted aliphatic unsaturated hydrocarbon group having 2 to 20 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms is preferable, An optionally substituted unsaturated chain hydrocarbon group having 2 to 10 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 10 carbon atoms is more preferable, An optionally substituted unsaturated chain hydrocarbon group having 2 to 7 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 8 carbon atoms is more preferable, An optionally substituted alkenyl group having 2 to 7 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 8 carbon atoms is more preferable, An optionally substituted ethenyl group or an optionally substituted phenyl group is particularly preferred.
  • ny5 to ny12 are each independently, for example, 0 to 2 or 4, preferably 0 to 2, more preferably 0 to 1, still more preferably 0.
  • X y5 to X y12 are each independently preferably -R y5 or a halogen atom, more preferably a linear or branched alkyl group having 1 to 10 carbon atoms, or a halogen atom, and 1 to 5 carbon atoms. is more preferred, and a tert-butyl group, a fluorine atom, a chlorine atom, or a bromine atom is particularly preferred.
  • At least one of Y2 , Zy4 and Zy5 represents a sulfur atom. However, when R y3 is an unsaturated aliphatic hydrocarbon group, Z y5 is preferably a single bond.
  • Compounds represented by formula (YI) include compounds represented by formulas (YIA) to (YIE).
  • Examples of the compound represented by formula (YIA) include compounds represented by formulas (YIA-1) to (YIA-24) shown in Table 26.
  • Examples of the compound represented by formula (YIB) include compounds represented by formulas (YIB-1) to (YIB-24) shown in Table 27.
  • Examples of the compound represented by formula (YIC) include compounds represented by formulas (YIC-1) to (YIC-24) shown in Table 28.
  • Examples of the compound represented by formula (YID) include compounds represented by formulas (YID-1) to (YID-24) shown in Table 29.
  • Examples of the compound represented by formula (YIE) include compounds represented by formulas (YIE-1) to (YIE-24) shown in Table 30. In Tables 26 to 30, "yi-1" represents a phenyl group, and "yi-2" represents an ethenyl group.
  • Formula (YIA) As the compound represented by the formula (YIA), Formula (YIA-1) ⁇ Formula (YIA-6), Formula (YIA-13) ⁇ Formula (YIA-18), Formula (YIA-21), Formula (YIA-22) ⁇ Formula (YIA-24) are preferred, Compounds represented by formula (YIA-1), formula (YIA-13), formula (YIA-21), formula (YIA-23) and formula (YIA-24) are more preferred.
  • Formula (YIB) As the compound represented by the formula (YIB), Formula (YIB-1) ⁇ Formula (YIB-6), Formula (YIB-13) ⁇ Formula (YIB-18), Formula (YIB-21), Formula (YIB-22) ⁇ Formula (YIB-24) are preferred, Compounds represented by formula (YIB-1), formula (YIB-13), formula (YIB-21), formula (YIB-23) and formula (YIB-24) are more preferred.
  • Formula (YIC-1) ⁇ Formula (YIC-6), Formula (YIC-13) ⁇ Formula (YIC-18), Formula (YIC-21), Formula (YIC-22) ⁇ Formula (YIC-24) are preferred, Compounds represented by formula (YIC-1), formula (YIC-13), formula (YIC-21), formula (YIC-23) and formula (YIC-24) are more preferred.
  • Formula (YID-1) ⁇ Formula (YID-6), Formula (YID-13) ⁇ Formula (YID-18), Formula (YID-21), Formula (YID-22) ⁇ Formula (YID-24) are preferred, Compounds represented by formula (YID-1), formula (YID-13), formula (YID-21), formula (YID-23) and formula (YID-24) are more preferred.
  • Formula (YIE-1) ⁇ Formula (YIE-6), Formula (YIE-13) ⁇ Formula (YIE-18), Formula (YIE-21), Formula (YIE-22) ⁇ Formula (YIE-24) are preferred, Compounds represented by Formula (YIE-1), Formula (YIE-13), Formula (YIE-21), Formula (YIE-23) and Formula (YIE-24) are more preferred.
  • Compounds represented by formula (YII) include compounds represented by formulas (YIIA) to (YIIE).
  • Compounds represented by formula (YIIA) include, for example, formula (YIIA-1) shown in Table 31 to the compound represented by the formula (YIIA-13).
  • Examples of the compound represented by formula (YIIB) include compounds represented by formulas (YIIB-1) to (YIIB-13) shown in Table 32.
  • Examples of the compound represented by formula (YIIC) include compounds represented by formulas (YIIC-1) to (YIIC-13) shown in Table 33.
  • Examples of the compound represented by the formula (YIID) include compounds represented by the formulas (YIID-1) to (YIID-13) shown in Table 34.
  • Examples of the compound represented by formula (YIIE) include compounds represented by formulas (YIIE-1) to (YIIE-13) shown in Table 35. In Tables 31 to 35, "yi-1" represents a phenyl group and "yi-2" represents an ethenyl group.
  • the compound represented by formula (YI) can be produced, for example, by appropriately reacting a compound represented by formula (YIII) with a compound represented by formula (YIV). Further, the compound represented by the formula (YII) can be produced, for example, by appropriately reacting the compounds represented by the formulas (YIIIa) and (YIIIb) with the compound represented by the formula (YV).
  • R y1 , R y2 , Y 1 , Z y1 , Z y2 , Z y3 , X y1 to X y4 and ny1 to ny4 are the same as above.
  • the aluminum phthalocyanine compound can be dispersed uniformly in the dispersant solution by adding a dispersant and performing a dispersion treatment.
  • the aluminum phthalocyanine compound may be subjected to dispersion treatment alone, or may be mixed with a plurality of types and subjected to dispersion treatment.
  • the same as the pigment dispersant described later can be used.
  • the amount used is preferably 10 parts by mass or more and 200 parts by mass or less, more preferably 15 parts by mass or more and 180 parts by mass or less, relative to 100 parts by mass of the aluminum phthalocyanine compound in the dispersion. It is preferably 20 parts by mass or more and 160 parts by mass or less. When the amount of the dispersant used is within the above range, there is a tendency to obtain a more uniformly dispersed liquid dispersion.
  • the content of the aluminum phthalocyanine compound is preferably 0.5 to 70% by mass, more preferably 1 to 55% by mass, still more preferably 2 to 50% by mass, based on the total solid content of the colored curable composition. Also, the content of the aluminum phthalocyanine compound may be 0.5 to 20% by mass based on the total solid content of the colored curable composition.
  • total amount of solids refers to the total amount of components of the colored curable composition of the present invention excluding the solvent. The total amount of solids and the content of each component relative thereto can be measured by known analysis means such as liquid chromatography and gas chromatography.
  • the content of the aluminum phthalocyanine compound is preferably 1 to 100% by mass, more preferably 3 to 80% by mass, still more preferably 5 to 70% by mass, based on the total amount of the colorant (A), Even more preferably, it is 5 to 60% by mass.
  • the coloring agent (A) may further contain a coloring agent different from the aluminum phthalocyanine compound (hereinafter sometimes referred to as coloring agent (A2)).
  • the coloring agent (A2) may be either a dye or a pigment, or a mixture thereof.
  • Dyes include, for example, compounds classified as having hues other than pigments in the Color Index (published by The Society of Dyers and Colourists), and known dyes listed in Stain Note (Shikisensha). be done.
  • dyes examples include azo dyes, cyanine dyes, triphenylmethane dyes, thiazole dyes, oxazine dyes, quinophthalone dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, Coumarin dyes, quinoline dyes, nitro dyes, and the like may be used, and known dyes are used.
  • dyes include C.I. I. Solvent Yellow 4 (hereinafter, the description of C.I. Solvent Yellow is omitted and only the number is described. The same applies to others.), 14, 15, 23, 24, 38, 62, 63, 68, 82 , 94, 99, 117, 162, 163, 167, 189; C. I. Solvent Red 111, 125, 130, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 222, 227, 230, 245, 247; C. I. Solvent Orange 2, 7, 11, 15, 26, 56, 77, 86; C. I.
  • C. I. C.I. I. solvent dyes C. I.
  • I. direct dye C. I. Disperse Yellow 51, 54, 76; C. I. Disperse Violet 26, 27; C. I. C.I. I. disperse dyes, C. I. basic blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89; C. I. basic violet 2; C. I. basic red 9; C. I. Basic Green 1; I. basic dye, C. I.
  • pigments examples include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colorists), and the following pigments can be exemplified.
  • Green pigment C.I. I. Pigment Green 7, 36, 58, 59, etc.
  • Yellow pigment 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, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, etc.
  • Orange pigment C.I. I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, etc.
  • Red pigment C.I. I.
  • one type of pigment or a plurality of pigments may be used for each color, and pigments of each color may be combined.
  • the pigment is subjected to rosin treatment, surface treatment using a pigment derivative into which an acidic or basic group has been introduced, graft treatment to the pigment surface with a polymer compound, etc., atomization by a sulfuric acid atomization method, etc. Treatment, washing treatment with an organic solvent or water for removing impurities, removal treatment by an ion exchange method for ionic impurities, or the like may be performed. It is preferable that the particle size of the pigment is substantially uniform.
  • the pigment can be dispersed uniformly in the dispersant solution by adding a pigment dispersant and performing a dispersion treatment.
  • the pigments may be subjected to dispersion treatment alone, or may be dispersed by mixing plural kinds of pigments.
  • pigment dispersants examples include surfactants, which may be cationic, anionic, nonionic or amphoteric surfactants. Specific examples include surfactants such as polyester-based, polyamine-based and acrylic-based surfactants. These dispersants may be used alone or in combination of two or more.
  • KP manufactured by Shin-Etsu Chemical Co., Ltd.
  • Floren manufactured by Kyoeisha Chemical Co., Ltd.
  • Solsperse registered trademark
  • EFKA registered trademark
  • the amount used is preferably 10 parts by mass or more and 200 parts by mass or less, more preferably 15 parts by mass or more and 180 parts by mass or less, and still more preferably 100 parts by mass of the pigment in the dispersion. is 20 parts by mass or more and 160 parts by mass or less.
  • the amount of the pigment dispersant used is within the above range, there is a tendency to obtain a dispersion with a more uniform dispersion state.
  • the content of the coloring agent (A2) is preferably 1 to 99% by mass, more preferably 1 to 97% by mass, based on the total amount of the coloring agent (A). , more preferably 20 to 95% by mass. Further, the content of the colorant (A2) may be 20 to 97% by mass, 30 to 95% by mass, or 40 to 95% by mass in the total amount of the colorant (A). may
  • the content of the coloring agent (A) in the colored curable composition is preferably 0.5 to 80% by mass, more preferably 5 to 70% by mass, more preferably 10 to 55% by mass, based on the total amount of solids. % by mass.
  • the content of the coloring agent (A) is within the above range, it becomes easier to obtain the desired spectrum and color density.
  • the resin (B) is not particularly limited, it is preferably an alkali-soluble resin.
  • the resin (B) include the following resins [K1] to [K6].
  • Resin [K1] at least one (a) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter sometimes referred to as "(a)"), and a cyclic ether having 2 to 4 carbon atoms
  • a copolymer with a monomer (b) having a structure and an ethylenically unsaturated bond hereinafter sometimes referred to as "(b)”
  • Resin [K2]; (a) and (b), and monomer (c) copolymerizable with (a) (but different from (a) and (b)) hereinafter “(c)” may be called) and a copolymer
  • Resin [K3] copolymer of (a) and (c)
  • (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid; Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinyl phthalic acid, 4-vinyl phthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyl Unsaturated dicarboxylic acids such as tetrahydrophthalic acid and 1,4-cyclohexenedicarboxylic acid; methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethyl
  • (b) is, for example, a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (eg, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring) and an ethylenically unsaturated bond.
  • (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.
  • (meth)acrylic acid represents at least one selected from the group consisting of acrylic acid and methacrylic acid. Notations such as "(meth)acryloyl" and "(meth)acrylate” have the same meaning.
  • Examples of (b) include a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)”), a monomer having an oxetanyl group and an ethylenically unsaturated bond, a monomer (b2) (hereinafter sometimes referred to as “(b2)”), a monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)”), etc. mentioned.
  • a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond hereinafter sometimes referred to as "(b1)
  • a monomer having an oxetanyl group and an ethylenically unsaturated bond hereinafter sometimes referred to as "(b2)
  • (b3) monomer having a tetrahydrofuryl group and an
  • (b1) for example, a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter referred to as "(b1-1)” ), and a monomer (b1-2) having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as “(b1-2)”).
  • (b1-1) includes glycidyl (meth)acrylate, ⁇ -methylglycidyl (meth)acrylate, ⁇ -ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p -vinylbenzyl glycidyl ether, ⁇ -methyl-o-vinylbenzyl glycidyl ether, ⁇ -methyl-m-vinylbenzyl glycidyl ether, ⁇ -methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyloxymethyl)styrene , 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxy
  • (b1-2) includes vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (eg, Celoxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (eg, Cychromer A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (eg, Cychromer M100; manufactured by Daicel Corporation), 3,4-epoxytricyclo [5.2.1. 0 2,6 ]decyl (meth)acrylate, a compound represented by formula (R1), a compound represented by formula (R2), and the like.
  • vinylcyclohexene monoxide eg, 1,2-epoxy-4-vinylcyclohexane (eg, Celoxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (eg, Cychromer A400; manufactured by Da
  • R ra and R rb represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group is substituted with a hydroxy group.
  • X ra and X rb represent a single bond, *-R rc -, *-R rc -O-, *-R rc -S- or *-R rc -NH-.
  • R rc represents an alkanediyl group having 1 to 6 carbon atoms. * represents a bond with O.
  • alkyl groups having 1 to 4 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group and tert-butyl group.
  • Alkyl groups in which hydrogen atoms are substituted with hydroxy include hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 1-hydroxy -1-methylethyl group, 2-hydroxy-1-methylethyl group, 1-hydroxybutyl group, 2-hydroxybutyl group, 3-hydroxybutyl group, 4-hydroxybutyl group and the like.
  • R ra and R rb 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.
  • the alkanediyl group includes methylene, ethylene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane- A 1,6-diyl group and the like can be mentioned.
  • X ra and X rb are preferably a single bond, a methylene group, an ethylene group, *--CH 2 --O-- and *--CH 2 CH 2 --O--, more preferably a single bond and *--CH 2 CH 2 --O-- (* represents a bond with O).
  • Examples of the compound represented by formula (R1) include compounds represented by any one of formulas (R1-1) to (R1-15). Among them, formula (R1-1), formula (R1-3), formula (R1-5), formula (R1-7), formula (R1-9) or formula (R1-11) to formula (R1-15) A compound represented by is preferable, and a compound represented by formula (R1-1), formula (R1-7), formula (R1-9) or formula (R1-15) is more preferable.
  • Examples of the compound represented by formula (R2) include compounds represented by any one of formulas (R2-1) to (R2-15). Among them, formula (R2-1), formula (R2-3), formula (R2-5), formula (R2-7), formula (R2-9) or formula (R2-11) to formula (R2-15) A compound represented by is preferable, and a compound represented by formula (R2-1), formula (R2-7), formula (R2-9) or formula (R2-15) is more preferable.
  • (b2) is more preferably a monomer having an oxetanyl group and a (meth)acryloyloxy group.
  • (b2) includes 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3-acryloyloxymethyloxetane , 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3-methacryloyloxyethyloxetane, 3-ethyl-3-acryloyloxyethyloxetane and the like.
  • (b3) is more preferably a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group.
  • Specific examples of (b3) include tetrahydrofurfuryl acrylate (eg, Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like.
  • (b) is preferably (b1) in that the heat resistance, chemical resistance, etc. of the obtained color filter can be made more reliable. Furthermore, (b1-2) is more preferable in that the storage stability of the colored curable composition is more excellent.
  • (c) includes, for example, 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[5.2.1.0 2,6 ]Decan-8-yl (meth)acrylate (in the technical field, it is commonly referred to as “dicyclopentanyl (meth)acrylate”.
  • tricyclodecyl (meth)acrylate tricyclo[5.2.1.0 2,6 ]decen-8-yl (meth)acrylate (in the art, it is commonly called “dicyclopentenyl (meth)acrylate”.
  • dicyclopentanyloxyethyl (meth)acrylate dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, benzyl (meth) acrylic acid esters such as (meth) acrylate; Hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate; bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5- Hydr
  • (c) includes 2-ethylhexyl (meth)acrylate, dicyclopentanyl (meth)acrylate, benzyl (meth)acrylate, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo [2.2.1] Hept-2-ene and the like are preferred, and from the viewpoint of copolymerization reactivity and heat resistance, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2 .2.1]hept-2-ene and the like are more preferred.
  • 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 curable composition, the developability when forming a colored pattern, and the solvent resistance of the resulting color filter tend to be excellent.
  • 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 of the solvent (G) include the solvents described later.
  • the obtained copolymer may be used as a solution after the reaction as it is, may be used as a concentrated or diluted solution, or may be taken out as a solid (powder) by a method such as reprecipitation. You can use things.
  • the solvent contained in the colored curable composition as a solvent during this polymerization, the solution after the reaction can be used as it is for the preparation of the colored curable composition, so that the colored curable composition
  • the manufacturing process of things 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 unit derived from (b); 2 to 95 mol% Structural unit 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 storage stability of the colored curable composition When the ratio of the structural units of the resin [K2] is within the above range, the storage stability of the colored curable composition, developability when forming a colored pattern, and the solvent resistance and heat resistance of the resulting color filter are improved. It tends to have excellent toughness and 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, triphenylphosphine, etc.) and a polymerization inhibitor (e.g., hydroquinone, metoquinone, etc.) are placed in a flask and reacted at, for example, 60 to 130 ° C. for 1 to 10 hours to obtain a resin [K4 ] can be manufactured.
  • a reaction catalyst e.g., tris ( Dimethylaminomethyl)phenol, triphenylphosphine, etc.
  • a polymerization inhibitor e.g., hydroquinone, metoquinone, 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 it to this range, the storage stability of the colored curable composition, the developability when forming a pattern, and the solvent resistance, heat resistance, mechanical strength and sensitivity of the resulting pattern tend to have a good balance.
  • (b1) is preferable as the (b) used in the resin [K4], and (b1-1) is more preferable.
  • the amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass 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 100 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 succinic anhydride, maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinyl phthalic anhydride, 4-vinyl phthalic anhydride, and 3,4,5,6-tetrahydrophthalic acid.
  • carboxylic acid anhydride is preferably 0.1 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; 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylate/benzyl (meth)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-epoxytricycl
  • Resin [K6] such as a resin obtained by further reacting a resin obtained by reacting acrylic acid with succinic anhydride.
  • resin (B) a structural unit derived from at least one selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides, a cyclic ether structure having 2 to 4 carbon atoms and ethylenically unsaturated A copolymer containing a structural unit having a bond (resin [K1] or resin [K2]) or resin [K6] is preferred.
  • the polystyrene-equivalent weight average molecular weight of the resin (B) is preferably 500 to 100,000, more preferably 600 to 50,000, still more preferably 700 to 30,000.
  • the molecular weight is within the above range, the hardness of the color filter is improved, the residual film rate is high, the solubility of the unexposed portion in the developing solution is good, and the resolution of the colored pattern tends to be improved.
  • the dispersion degree [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the resin (B) is preferably 1.1-6, more preferably 1.2-4.
  • the acid value of the resin (B) is preferably 10-170 mg-KOH/g, more preferably 20-150 mg-KOH/g, still more preferably 30-135 mg-KOH/g, in terms of solid content.
  • the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be determined, for example, by titration using an aqueous potassium hydroxide solution. .
  • the content of the resin (B) is preferably 7 to 80% by mass, more preferably 13 to 75% by mass, still more preferably 17 to 70% by mass, and even more preferably, relative to the total solid content. is 17 to 55% by mass.
  • the content of the resin (B) is within the above range, a colored pattern can be formed, and the resolution of the colored pattern and the residual film rate tend to be improved.
  • the polymerizable compound (C) is a compound that can be polymerized by an active radical and/or an acid generated from the polymerization initiator (D). is a (meth)acrylic acid ester compound.
  • 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 oxide-modified pent
  • At least one selected from the group consisting of trimethylolpropane tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, and ethylene oxide-modified dipentaerythritol hexa(meth)acrylate is preferred.
  • the weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, more preferably 250 or more and 1,500 or less.
  • the content of the polymerizable compound (C) is preferably 7 to 65% by mass, more preferably 10 to 60% by mass, still more preferably 12 to 55% by mass, based on the total solid content. be.
  • the content of the polymerizable compound (C) is within the above range, there is a tendency that the residual film ratio at the time of forming the colored pattern and the chemical resistance of the color filter are improved.
  • the polymerization initiator (D) is a compound capable of initiating polymerization by generating active radicals, acids, etc. by the action of light or heat.
  • the colored curable composition of the present invention contains an oxime compound as a polymerization initiator (D).
  • the oxime compound is preferably an O-acyl oxime compound having a partial structure represented by formula (d1). Below, * represents a bond.
  • Examples of the oxime compound include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1- On-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2- methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6- ⁇ 2-methyl-4-(3,3-dimethyl-2,4-di Oxacyclopentanylmethyloxy)benzoyl ⁇ -9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)
  • Irgacure OXE01, OXE02, OXE03 (manufactured by BASF), N-1919 (manufactured by ADEKA), PBG-314, PBG-317, PBG-326, PBG-327, PBG-329 (manufactured by Changzhou Power Electronics New Materials Co., Ltd.) ) may be used.
  • oxime compounds include N-acetyloxy-1-[4-(2-hydroxyethyloxy)phenylsulfanylphenyl]propan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl )-3-cyclohexylpropan-1-one-2-imine, 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propan-1-one, N-benzoyloxy -1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine and N-benzoyloxy-1 At least one selected from the group consisting of -(4-phenylsulfanylphenyl)-3-cyclopentylprop
  • the colored curable composition of the present invention may contain a polymerization initiator other than the oxime compound as the polymerization initiator (D).
  • a polymerization initiator other than the oxime compound as the polymerization initiator (D).
  • examples of other polymerization initiators include alkylphenone compounds and triazines.
  • polymerization initiators that generate active radicals such as compounds, acylphosphine oxide compounds and biimidazole compounds.
  • the alkylphenone compound is a compound having a partial structure represented by formula (d2) or a partial structure represented by formula (d3).
  • the benzene ring may have a substituent.
  • Examples of compounds having a partial structure represented by formula (d2) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4 -morpholinophenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one etc.
  • Commercially available products such as Irgacure 369, 907 and 379 (manufactured by BASF) may also be used.
  • Examples of compounds having a partial structure represented by formula (d3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2 -hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexylphenyl ketone, oligomer of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, ⁇ , ⁇ -diethoxy Acetophenone, benzyl dimethyl ketal and the like can be mentioned.
  • the alkylphenone compound is preferably a compound having a partial structure represented by formula (d2).
  • triazine compound examples include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4- methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxy styryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4 -bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,
  • acylphosphine oxide compound examples include 2,4,6-trimethylbenzoyldiphenylphosphine oxide.
  • Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) may also be used.
  • biimidazole compound examples include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)- 4,4',5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372 and JP-A-6-75373), 2,2'-bis(2-chlorophenyl)-4 ,4′,5,5′-tetraphenylbiimidazole, 2,2′-bis(2-chlorophenyl)-4,4′,5,5′-tetra(alkoxyphenyl)biimidazole, 2,2′-bis (2-chlorophenyl)-4,4′,5,5′-tetra(dialkoxyphenyl)biimidazole, 2,2′-bis(2-chlorophenyl)-4,4′,5,5′-tetra(triphen
  • Further polymerization initiators include 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-4; Benzophenone compounds such as '-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, 2,4,6-trimethylbenzophenone; 9,10-phenanthrenequinone, 2 -quinone compounds such as ethylanthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, titanocene compounds and the like. These are preferably used in combination with a polymerization initiation aid (D1) (particularly
  • polymerization initiators include, for example, 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetoxyphenyl Onium salts such as methylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, diphenyliodonium hexafluoroantimonate, and nitrobenzyl tosylates , acid-generating polymerization initiators such as benzoin tosylate.
  • the content of the oxime compound in the polymerization initiator (D) is preferably 50% by mass or more, more preferably 80% by mass or more, still more preferably 90% by mass or more, still more preferably 95% by mass or more, and particularly preferably It is 98% by mass or more, and may be 100% by mass.
  • the content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, with respect to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). part by mass.
  • 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 polymerization initiation aid (D1) is a compound or a sensitizer used to accelerate the polymerization of the polymerizable compound whose polymerization has been initiated by the polymerization initiator. When 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 compound examples include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 4 -2-ethylhexyl dimethylaminobenzoate, N,N-dimethyl p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, 4,4'-bis (Ethylmethylamino)benzophenone and the like can be mentioned, and 4,4′-bis(diethylamino)benzophenone is particularly preferable.
  • 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-di butoxyanthracene, 2-ethyl-9,10-dibutoxyanthracene and the like.
  • thioxanthone compounds examples 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, naphthoxyacetic acid and the like.
  • the content is preferably 0.1 to 30 parts by mass, with respect to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). It is preferably 1 to 20 parts by mass.
  • the amount of the polymerization initiation aid (D1) is within this range, a colored pattern can be formed with higher sensitivity, and the productivity of color filters tends to improve.
  • the latent antioxidant (E) is a compound in which the active group of the antioxidant is protected with a protective group.
  • the latent antioxidant (E) is preferably a compound in which the phenolic hydroxyl group of the phenolic antioxidant is protected by a protective group, and the phenolic hydroxyl group of the hindered phenolic antioxidant is a protective group. It is more preferable that it is a compound protected with.
  • Examples of the protecting group for protecting the phenolic hydroxyl group include ether-based protecting groups, acetal-based protecting groups, acyl-based protecting groups, carbonate-based protecting groups, and silyl-based protecting groups. Among them, carbonate-based protecting groups are preferred. .
  • the ether-based protecting group is —OR p1 (O represents an oxygen atom constituting a phenolic hydroxyl group.
  • R p1 represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. ) is preferably a group represented by —R p1 .
  • Hydrocarbon groups having 1 to 20 carbon atoms represented by R p1 include R b1 to R b3 , R x2 , R x4 , R x5 , R x11 to R x13 , R x15 to R x17 , R y1 to R y5 , R y11 to R y13 and R y15 to R y17 , the hydrocarbon groups having 1 to 20 carbon atoms are exemplified, and saturated chain alkyl groups such as straight-chain alkyl groups and branched-chain alkyl groups are mentioned.
  • the hydrocarbon group having 1 to 20 carbon atoms represented by R p1 may have a substituent, and the substituent includes a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a nitro group. , a cyano group, —OR xa1 , —CO 2 R xa1 , —SR xa1 , —SO 2 R xa1 , —SO 3 R xa1 , —SO 2 NR xa1 R xa2 and —NR xa1 R xa2 (with the proviso that R xa1 and R xa2 are the same as above).
  • a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom
  • a cyano group —OR xa1 , —CO 2 R xa1
  • R p1 is an optionally substituted linear or branched C 1-20 alkyl group, an optionally substituted C 6-20 aromatic hydrocarbon It is preferably a hydrogen group or an aralkyl group having 7 to 20 carbon atoms which may have a substituent, and a linear or branched chain having 1 to 10 carbon atoms which may have a substituent. , an optionally substituted aromatic hydrocarbon group having 6 to 10 carbon atoms, or an optionally substituted aralkyl group having 7 to 10 carbon atoms, A methyl group, an ethyl group, a tert-butyl group, a phenyl group, a benzyl group, or a p-methoxybenzyl group are more preferred.
  • the acetal protecting group is -O 1 -L p2 -O 2 -R p2 (O 1 represents an oxygen atom constituting a phenolic hydroxyl group, O 2 represents an oxygen atom constituting a protecting group, L p2 represents a carbon represents an alkylene group of number 1 to 10, and R p2 represents a hydrocarbon group optionally having a substituent of 1 to 20 carbon atoms, and L p2 and R p2 may combine with each other to form a ring; It is preferably a group represented by -L p2 -O 2 -R p2 in ).
  • L p2 is preferably a linear alkylene group having 1 to 10 carbon atoms, more preferably a linear alkylene group having 1 to 5 carbon atoms, and is a methylene group, ethylene group, or propylene group. It is even more preferable to have
  • the optionally substituted hydrocarbon group represented by R p2 having 1 to 20 carbon atoms is an optionally substituted hydrocarbon group represented by R p1 having 1 to 20 carbon atoms.
  • the group explained as the group can be mentioned.
  • R p2 is an optionally substituted linear or branched C 1-20 alkyl group, an optionally substituted C 6-20 aromatic hydrocarbon It is preferably a hydrogen group or an aralkyl group having 7 to 20 carbon atoms which may have a substituent, and a linear or branched chain having 1 to 10 carbon atoms which may have a substituent. or an optionally substituted aralkyl group having 7 to 10 carbon atoms, a methyl group, an ethyl group, a propyl group, a butyl group, a benzyl group, a methoxymethyl group, 2- A methoxyethyl group, an ethoxymethyl group, or an ethoxyethyl group is more preferred.
  • acetal protective groups include methoxymethyl group, ethoxymethyl group, propoxymethyl group, butoxyethyl group, benzyloxyethyl group, methoxymethoxyethyl group, 2-methoxyethoxymethyl group, ethoxymethoxyethyl group, ethoxy ethoxyethyl group, 2-tetrahydropyranyl group and the like.
  • the optionally substituted hydrocarbon group represented by R p3 having 1 to 20 carbon atoms is a hydrocarbon group having 1 to 20 carbon atoms optionally having substituent(s) represented by R p1 .
  • the group explained as the group can be mentioned.
  • R p3 is a hydrogen atom, an optionally substituted C 1-20 saturated or unsaturated chain hydrocarbon group, an optionally substituted C 6-20 aromatic It is preferably a hydrocarbon group or an optionally substituted aralkyl group having 7 to 20 carbon atoms, a hydrogen atom, or a saturated or unsaturated group having 1 to 10 carbon atoms which may have a substituent. It is more preferably a chain hydrocarbon group or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, such as a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, and an isopropyl group. , n-butyl group, isobutyl group, tert-butyl group, vinyl group, 1-methylethenyl group, propenyl group or phenyl group are more preferable.
  • acyl-based protective groups include formyl, acetyl, propionyl, butyryl, pivaloyl, acryloyl, methacryloyl, crotonoyl, and benzoyl groups.
  • the optionally substituted hydrocarbon group represented by R p4 having 1 to 20 carbon atoms is a hydrocarbon group having 1 to 20 carbon atoms optionally having substituent(s) represented by R p1 .
  • the group explained as the group can be mentioned.
  • R p4 is an optionally substituted C 1-20 saturated or unsaturated chain hydrocarbon group, an optionally substituted C 6-20 aromatic hydrocarbon group. , or preferably an aralkyl group having 7 to 20 carbon atoms which may have a substituent, a saturated or unsaturated chain hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, or an optionally substituted aralkyl group having 7 to 15 carbon atoms, a methyl group optionally having a halogen atom, an ethyl group optionally having a halogen atom, a halogen A tert-butyl group, an allyl group, a benzyl group, or a 9-fluorenylmethyl group, which may have atoms, are more preferred.
  • carbonate-based protective groups include a tert-butyloxycarbonyl group, 2,2,2-trichloroethyloxycarbonyl group, allyloxycarbonyl group, benzyloxycarbonyl group, 9-fluorenylmethyloxycarbonyl group, and the like. is mentioned.
  • the silyl protecting group is —O—Si(R p5 ) 3 (O represents an oxygen atom constituting a phenolic hydroxyl group, R p5 is a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent A plurality of R p5 may be the same or different), and is preferably a group represented by —Si(R p5 ) 3 .
  • the optionally substituted hydrocarbon group represented by R p5 having 1 to 20 carbon atoms is an optionally substituted hydrocarbon group represented by R p1 having 1 to 20 carbon atoms.
  • the group explained as the group can be mentioned.
  • Each R p5 is independently an optionally substituted linear or branched C 1-20 alkyl group, an optionally substituted C 6-20 or an aralkyl group having 7 to 20 carbon atoms which may have a substituent, each independently having 1 to 10 carbon atoms which may have a substituent It is more preferably a linear or branched alkyl group, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, each independently methyl group, ethyl group, More preferred are n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, or phenyl groups.
  • silyl-based protecting groups include trimethylsilyl group, triethylsilyl group, tert-butyldimethylsilyl group, triisopropylsilyl group, tert-butyldiphenylsilyl group and the like.
  • the latent antioxidant (E) is more preferably a compound represented by formula (E-1).
  • X a represents an n-valent organic group.
  • n represents an integer of 1-4.
  • X 0 represents a phenolic hydroxyl-protecting group.
  • m represents an integer of 1 to 4;
  • X 4 represents an optionally substituted hydrocarbon group having 1 to 20 carbon atoms, and when m is 2 or more, multiple X 4s may be the same or different.
  • n-valent organic group represented by X a is not particularly limited, the following aspects (a) to (d) are preferred.
  • X a is preferably a hydrocarbon group having 1 to 20 carbon atoms.
  • the hydrocarbon group has 2 to 20 carbon atoms and the hydrocarbon group has --CH 2 --, the --CH 2 -- is --O--, --CO--, --O--CO-- or --- CO--O-- may be substituted.
  • adjacent --CH 2 -- are not substituted at the same time, and terminal --CH 2 -- is never substituted.
  • the hydrocarbon groups having 1 to 20 carbon atoms are R b1 to R b3 , R x2 , R x4 , R x5 , R x11 to R x13 , R x15 to R x17 , R y1 to R y5 , R y11 to R y13 and groups exemplified as hydrocarbon groups having 1 to 20 carbon atoms represented by R y15 to R y17 , saturated chain hydrocarbon groups such as linear alkyl groups and branched alkyl groups, alkenyl groups , unsaturated chain hydrocarbon groups such as alkynyl groups, saturated alicyclic hydrocarbon groups such as cycloalkyl groups, unsaturated alicyclic hydrocarbon groups such as cycloalkenyl groups, and saturated or unsaturated polycyclic hydrocarbon groups aromatic hydrocarbon groups; and groups combining the above hydrocarbon groups, such as aralkyl groups, arylalkenyl groups, and phenyl groups to which one or
  • X a is a linear or branched alkyl group having 1 to 8 carbon atoms, wherein at least one of —CH 2 — constituting the alkyl group is —O—CO - or a group optionally substituted with -CO-O-, a cycloalkyl group having 3 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms, wherein -CH 2 - constituting the aralkyl group A group in which at least one of which may be replaced with -O-CO- or -CO-O- is preferred.
  • X a is preferably a group represented by formula (e-2).
  • Z 1 and Z 2 are each independently a single bond or an alkylene group having 1 to 20 carbon atoms, and at least one of —CH 2 — constituting the alkylene group is —O—, —CO—, — It may be replaced by O—CO— or —CO—O—. However, adjacent --CH 2 -- are not substituted at the same time.
  • Y e2 represents a divalent hydrocarbon group having 1 to 30 (preferably 1 to 20) carbon atoms. When the hydrocarbon group has -CH 2 -, at least one of -CH 2 - is replaced with -O-, -S-, -CO-, -O-CO- or -CO-O-. may However, adjacent --CH 2 -- are not substituted at the same time. * indicates a bond.
  • the divalent hydrocarbon group having 1 to 20 carbon atoms represented by Y e2 is R b1 to R b3 , R x2 , R x4 , R x5 , R x11 to R x13 , R x15 to R x17 , R y1 to Examples include groups in which one of the hydrogen atoms of the groups exemplified as the hydrocarbon groups represented by R y5 , R y11 to R y13 and R y15 to R y17 is replaced with a bond.
  • the group represented by formula (e-2) is preferably any one of the groups represented by formulas (eb-1) to (eb-20).
  • Z 1 and Z 2 are the same as above.
  • p represents an integer of 1-19
  • q represents an integer of 1-3
  • r represents an integer of 0-3. * indicates a bond.
  • X a is preferably a group represented by formula (e-3).
  • Z 3 to Z 5 are each independently a single bond or an alkylene group having 1 to 20 carbon atoms, and at least one of —CH 2 — constituting the alkylene group is —O—, —CO—, — It may be replaced by O—CO— or —CO—O—. However, adjacent --CH 2 -- are not substituted at the same time.
  • Y e3 represents a trivalent hydrocarbon group having 1 to 20 carbon atoms or a trivalent heterocyclic group having 1 to 20 carbon atoms. When the hydrocarbon group and heterocyclic group have -CH 2 -, at least one of -CH 2 - is replaced with -O-, -CO-, -O-CO- or -CO-O-. may However, adjacent --CH 2 -- are not substituted at the same time. * indicates a bond.
  • the trivalent hydrocarbon group having 1 to 20 carbon atoms represented by Y e3 is R b1 to R b3 , R x2 , R x4 , R x5 , R x11 to R x13 , R x15 to R x17 , R y1 to Examples include groups in which two of the hydrogen atoms of the groups exemplified as the hydrocarbon groups represented by R y5 , R y11 to R y13 and R y15 to R y17 are replaced with bonds.
  • heterocyclic ring constituting the trivalent heterocyclic group having 1 to 20 carbon atoms represented by Y e3
  • Examples include the heterocyclic rings described for the heterocyclic group used as the group.
  • the group represented by formula (e-3) is preferably any one of the groups represented by formulas (ec-1) to (ec-15).
  • Z 3 to Z 5 are the same as above.
  • R ec1 to R ec3 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms.
  • p and r are the same as above. * indicates a bond.
  • X a is preferably a group represented by formula (e-4).
  • Z 6 to Z 9 are each independently a single bond or an alkylene group having 1 to 20 carbon atoms, and at least one of —CH 2 — constituting the alkylene group is —O—, —CO—, — It may be replaced by O—CO— or —CO—O—. However, adjacent --CH 2 -- are not substituted at the same time.
  • Y e4 represents a tetravalent hydrocarbon group having 1 to 20 carbon atoms. When the hydrocarbon group and -CH 2 - are present, at least one of -CH 2 - may be replaced with -O-, -CO-, -O-CO- or -CO-O-. . However, adjacent --CH 2 -- are not substituted at the same time. * indicates a bond.
  • the tetravalent hydrocarbon group having 1 to 20 carbon atoms represented by Y e4 is R b1 to R b3 , R x2 , R x4 , R x5 , R x11 to R x13 , R x15 to R x17 , R y1 to Examples thereof include groups in which three of the hydrogen atoms of the groups exemplified as the hydrocarbon groups represented by R y5 , R y11 to R y13 and R y15 to R y17 are replaced with bonds.
  • the group represented by formula (e-4) is preferably any one of the groups represented by formulas (ed-1) to (ed-5).
  • Z 6 to Z 9 are the same as above.
  • Z represents an alkylene group having 1 to 10 carbon atoms, and at least one of -CH 2 - constituting the alkylene group is -O-, -CO-, -O-CO- or -CO-O- may be replaced. However, adjacent --CH 2 -- are not substituted at the same time.
  • R ed1 and R ed2 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. * indicates a bond.
  • the alkylene groups represented by Z 1 to Z 9 and Z may be linear or branched.
  • the alkylene groups represented by Z 1 to Z 9 and Z are each independently preferably an alkylene group having 1 to 8 carbon atoms such as a methylene group, ethylene group, propylene group and butylene group.
  • Z 1 to Z 9 are each independently a single bond or an alkylene group having 1 to 8 carbon atoms, wherein at least one of —CH 2 — constituting the alkylene group is —O—, —CO -, -O-CO- or -CO-O- is preferably a group optionally substituted, each independently a single bond or an alkylene group having 1 to 8 carbon atoms, wherein at least one of —CH 2 — constituting the alkylene group is replaced with —O—CO— or —CO—O— is more preferably a group that may be Z 1 to Z 9 may be the same or different, but Z 1 and Z 2 are preferably the same, Z 3 to Z 5 are preferably the same, and Z 6 to Z 9 are preferably identical.
  • Z is preferably an alkylene group having 1 to 8 carbon atoms.
  • the hydrocarbon groups having 1 to 20 carbon atoms represented by R ec1 to R ec3 , R ed1 and R ed2 are R b1 to R b3 , R x2 , R x4 , R x5 , R x11 to R x13 , R x15 to
  • Examples of hydrocarbon groups represented by R x17 , R y1 to R y5 , R y11 to R y13 and R y15 to R y17 include saturated hydrocarbon groups such as straight-chain alkyl groups and branched-chain alkyl groups.
  • Chain hydrocarbon groups alkenyl groups, unsaturated chain hydrocarbon groups such as alkynyl groups, saturated alicyclic hydrocarbon groups such as cycloalkyl groups, unsaturated alicyclic hydrocarbon groups such as cycloalkenyl groups, and saturated or an aliphatic hydrocarbon group such as an unsaturated polycyclic hydrocarbon group; or any other group.
  • the number of carbon atoms in the hydrocarbon groups represented by R ec1 to R ec3 , R ed1 and R ed2 is preferably 1-10, more preferably 1-8, even more preferably 1-4.
  • R ec1 to R ec3 , R ed1 and R ed2 each independently represents a hydrogen atom, a linear or branched alkyl group having 1 to 8 carbon atoms (preferably 1 to 4), or 3 to 4 carbon atoms.
  • a cycloalkyl group of 8 is preferred.
  • X a is preferably any one of the groups represented by formulas (ec-1) to (ec-15) and formulas (ed-1) to (ed-5), and the formula (ed- 1) to (ed-5), and more preferably a group represented by formula (ed-1).
  • the bonding position of X a is not particularly limited, but it is preferably bonded at the para-position with respect to the oxygen atom bonding position.
  • Examples of X 0 include the groups described above as protective groups for protecting phenolic hydroxyl groups, and preferred embodiments are also the same.
  • m is preferably 1 or 2.
  • Hydrocarbon groups having 1 to 20 carbon atoms represented by X 4 include R b1 to R b3 , R x2 , R x4 , R x5 , R x11 to R x13 , R x15 to R x17 , R y1 to R y5 , R y11 to R y13 and R y15 to R y17 include saturated chain hydrocarbon groups such as straight-chain alkyl groups and branched-chain alkyl groups, alkenyl groups , unsaturated chain hydrocarbon groups such as alkynyl groups, saturated alicyclic hydrocarbon groups such as cycloalkyl groups, unsaturated alicyclic hydrocarbon groups such as cycloalkenyl groups, and saturated or unsaturated polycyclic hydrocarbon groups aromatic hydrocarbon groups; and groups combining the above hydrocarbon groups, such as aralkyl groups, arylalkenyl groups, and phenyl groups to which one or more phenyl groups are attached. good too.
  • the hydrocarbon group having 1 to 20 carbon atoms represented by X 4 may have a substituent, and examples of the substituent include a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a nitro group.
  • a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a nitro group.
  • X 4 is preferably a linear or branched alkyl group having 1 to 20 carbon atoms which may have a substituent, and a linear or branched chain having 1 to 10 carbon atoms.
  • a linear alkyl group is more preferable, and a straight-chain or branched-chain alkyl group having 1 to 4 carbon atoms is more preferable.
  • at least one of m X 4 is preferably a tertiary alkyl group having 4 to 10 carbon atoms, and at least one of m X 4 is a tert-butyl group or a tert-pentyl group. is particularly preferred.
  • substitution position of X 4 is not particularly limited, it is preferable that X 4 is bonded to at least one ortho position with respect to the position to which the oxygen atom is bonded, and X 4 is bonded to two ortho positions. is more preferable.
  • the latent antioxidant (E) is more preferably a compound represented by formula (E-2).
  • X 1 , X 2 and X 3 each independently represent a hydrocarbon group having 1 to 10 carbon atoms.
  • X a , n, X 4 and m are the same as above.
  • Hydrocarbon groups having 1 to 10 carbon atoms represented by X 1 to X 3 include R b1 to R b3 , R x2 , R x4 , R x5 , R x11 to R x13 , R x15 to R x17 , R y1 -R y5 , R y11 -R y13 and R y15 -R y17
  • groups having 1 to 10 carbon atoms can be mentioned, linear alkyl groups, branched Saturated chain hydrocarbon groups such as chain alkyl groups, unsaturated chain hydrocarbon groups such as alkenyl groups and alkynyl groups, saturated alicyclic hydrocarbon groups such as cycloalkyl groups, unsaturated alicyclic groups such as cycloalkenyl groups and aliphatic hydrocarbon groups such as saturated or unsaturated polycyclic hydrocarbon groups; aromatic hydrocarbon groups; and
  • X 1 to X 3 are each independently preferably a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent, and each independently 1 to 4 linear alkyl groups are more preferable, and each independently a methyl group or an ethyl group is more preferable.
  • the latent antioxidant (E) is particularly preferably a compound represented by formula (E-3).
  • X 10 represents a tertiary alkyl group having 4 to 20 carbon atoms.
  • s represents an integer from 0 to 3;
  • X a , n, and X 1 to X 4 are the same as above.
  • X 10 is preferably a tertiary alkyl group having 4 to 10 carbon atoms, more preferably a tert-butyl group or a tert-pentyl group.
  • s is preferably 0 or 1.
  • X 4 is preferably bonded at the ortho-position to the oxygen atom bonding position.
  • X 4 is preferably a tertiary alkyl group having 4 to 10 carbon atoms, more preferably a tert-butyl group or a tert-pentyl group.
  • the content of the latent antioxidant (E) is, for example, 1% by mass or more, preferably 2% by mass or more, more preferably 3% by mass or more, and for example 20% by mass or less, relative to the total amount of solids. , preferably 15% by mass or less, more preferably 10% by mass or less. Further, the content of the latent antioxidant (E) is, for example, 25 parts by mass or more, preferably 100 parts by mass or more, more preferably 150 parts by mass or more, and still more preferably 180 parts by mass with respect to 100 parts by mass of the aluminum phthalocyanine compound. It is at least 350 parts by mass, preferably 300 parts by mass or less, and more preferably 250 parts by mass or less.
  • the content ratio of the latent antioxidant (E) to the polymerization initiator (D) is, for example, 0.5 or more, preferably 1 or more, It is more preferably 2 or more, and is, for example, 10 or less, preferably 8 or less, and more preferably 5 or less.
  • the amount of the latent antioxidant (E) is within the above range, it is possible to provide a colored curable composition with better pattern stability even after storage.
  • 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 having a siloxane bond in the molecule.
  • 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 examples include surfactants having a fluorocarbon chain in the molecule.
  • 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 0.001 to 0.2% by mass, more preferably 0.002 to 0.1% by mass, more preferably 0.002 to 0.1% by mass, based on the total amount of the colored curable composition. is 0.005 to 0.05% by mass. This content does not include the content of the pigment dispersant. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.
  • the solvent (G) is not particularly limited, and solvents commonly used in the field can be used.
  • solvents commonly used in the field can be used.
  • ester solvent solvent containing -COO- in the molecule but not containing -O-
  • ether solvent solvent containing -O- in the molecule but not containing -COO-
  • ether ester solvent solvent containing -COO- in the molecule solvent containing -COO- and -O-
  • ketone solvent solvent containing -CO- in the molecule and not containing -COO-
  • alcohol solvent containing OH in the molecule, -O-, - solvents containing no CO- and -COO-
  • aromatic hydrocarbon solvents amide solvents, dimethyl sulfoxide and the like.
  • 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 and 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 (sometimes referred to as diacetone alcohol), acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2- Pentanone, cyclopentanone, 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.
  • Solvent (G) is preferably one or more selected from the group consisting of ether solvents, ether ester solvents and amide solvents, more preferably includes ether solvents, ether ester solvents and amide solvents, diethylene glycol methyl ethyl More preferred are ethers, propylene glycol monomethyl ether acetate, and N-methylpyrrolidone. Moreover, the solvent (G) preferably contains one or more selected from the group consisting of ether ester solvents and ketone solvents.
  • organic solvents having a boiling point of 120° C. or higher and 180° C. or lower at 1 atm are preferable from the viewpoint of coating properties and drying properties.
  • Such solvents include propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl- It is preferably at least one selected from the group consisting of 2-pentanone and N,N-dimethylformamide, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, ethyl 3-ethoxypropionate, and 4- More preferably, it is at least one selected from the group consisting of hydroxy-4-methyl-2-pentanone.
  • the content of the solvent (G) is preferably 70-95% by mass, more preferably 75-92% by mass, relative to the total amount of the colored curable composition.
  • the solids content of the colored curable composition is preferably 5-30% by weight, more preferably 8-25% by weight.
  • the colored curable composition may optionally contain additives known in the art such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents, etc. .
  • the colored curable composition includes, for example, a colorant (A) containing an aluminum phthalocyanine compound, a resin (B), a polymerizable compound (C), a polymerization initiator (D), and a latent antioxidant (E), and It can be prepared by mixing a polymerization initiation aid (D1), a leveling agent (F), a solvent (G) and other components used as necessary.
  • the aluminum phthalocyanine compound may be included in the dispersion in advance.
  • the pigment may also be included in the dispersion in advance.
  • the aluminum phthalocyanine compound and the pigment may be prepared as one dispersion, or may be prepared as separate dispersions.
  • the desired colored curable composition can be prepared by mixing the remaining components with the dispersion liquid so as to have a predetermined concentration.
  • the dye may be dissolved in part or all of the solvent (G) in advance to prepare a solution. It is preferable to filter the solution through a filter having a pore size of about 0.01 to 1 ⁇ m. It is preferable to filter the colored curable composition after mixing through a filter having a pore size of about 0.01 to 10 ⁇ m.
  • Examples of the method for producing a colored pattern of a color filter from the colored curable composition of the present invention include a photolithography method, an inkjet method, a printing method and the like. Among them, the photolithographic method is preferred. Photolithography is a method in which the colored curable composition is applied to a substrate, dried to form a composition layer, exposed through a photomask, and developed. In the photolithographic method, a colored coating film, which is a cured product of the 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 (colored coating film) is, for example, 30 ⁇ m or less, preferably 20 ⁇ m or less, more preferably 6 ⁇ m or less, even more preferably 3 ⁇ m or less, even more preferably 1.5 ⁇ m or less, and particularly preferably 0.5 ⁇ m or less. , preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more, and still more preferably 0.3 ⁇ m or more.
  • the substrate examples include glass plates such as quartz glass, borosilicate glass, alumina silicate glass, and soda-lime glass whose surface is coated with silica; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate; A thin film of aluminum, silver, silver/copper/palladium alloy, etc. is formed on the substrate. Other color filter layers, resin layers, transistors, circuits, and the like may be formed on these substrates. Alternatively, a substrate obtained by subjecting a silicon substrate to HMDS processing may be used.
  • each color pixel by the photolithographic method can be carried out using a known or commonly used apparatus and conditions. For example, it can be produced as follows. First, a colored curable 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 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 to 120°C, more preferably 50 to 110°C.
  • the heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes.
  • drying under reduced pressure it is preferably carried out at a pressure of 50 to 150 Pa and a temperature of 20 to 25°C.
  • the film thickness of the composition layer is not particularly limited, and may be appropriately selected according to the desired film thickness of the color filter.
  • the composition layer is then 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 light source used for exposure is preferably a light source that emits light with a wavelength of 250 to 450 nm. 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 reduction projection exposure apparatus such as a mask aligner and a stepper, or a proximity exposure apparatus. preferable.
  • a colored pattern is formed on the substrate by developing the exposed composition layer in contact with a developer.
  • a 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 to 10% by mass, more preferably 0.03 to 5% by mass.
  • the developer may contain a surfactant.
  • the developing method may be any of a puddle method, a dipping method, a spray method, and the like.
  • the substrate may be tilted at any angle during development. It is preferable to wash with water after development.
  • the post-baking temperature is preferably 80 to 250°C, more preferably 100 to 245°C.
  • Post-baking time is preferably 1 to 120 minutes, more preferably 2 to 30 minutes.
  • the colored pattern and colored coating film thus obtained are useful as a color filter, and the color filter can be used for display devices (e.g., liquid crystal display devices, organic EL display devices, etc.), electronic paper, solid-state imaging devices, and the like. It is useful as a color filter used for display devices (e.g., liquid crystal display devices, organic EL display devices, etc.), electronic paper, solid-state imaging devices, and the like. It is useful as a color filter used for display devices (e.g., liquid crystal display devices, organic EL display devices, etc.), electronic paper, solid-state imaging devices, and the like. It is useful as a color filter used for
  • Resin (B-1) has the following structural units.
  • the mixture was further stirred at 120° C. for 30 minutes to carry out a copolymerization reaction to produce an addition copolymer. Thereafter, the inside of the flask was replaced with air, and 93.7 parts of acrylic acid, 1.5 parts of triphenylphosphine (catalyst) and 0.8 parts of methoquinone (polymerization inhibitor) were introduced into the above addition copolymer solution.
  • the reaction was continued at 110° C. for 10 hours to cleave the epoxy group and introduce a polymerizable unsaturated bond into the side chain of the polymer at the same time as the reaction between the epoxy group derived from glycidyl methacrylate and acrylic acid.
  • Dispersion 1 (Preparation of Dispersion 1) C. I. Pigment Blue 15: 12.0 parts of 4, 3.6 parts of dispersant (BYKLPN-6919 manufactured by BYK), 5.4 parts of resin (B-1) (solid content conversion), propylene glycol monomethyl ether acetate 79 The parts were mixed and 300 parts of 0.4 mm zirconia beads were added and shaken for 1 hour using paint conditioner (manufactured by LAU). After that, the zirconia beads were removed by filtration to obtain Dispersion Liquid 1.
  • dispersion liquid 2 (Preparation of dispersion liquid 2) 5.0 parts of the compound (x1), 4.0 parts of the dispersant (BYKLPN-6919 manufactured by BYK), 4.0 parts of the resin (B-1) (in terms of solid content), 87 parts of propylene glycol monomethyl ether acetate was mixed, 300 parts of 0.4 mm zirconia beads were added and shaken for 1 hour using a paint conditioner (manufactured by LAU). After that, the zirconia beads were removed by filtration to obtain Dispersion Liquid 2.
  • a paint conditioner manufactured by LAU
  • dispersion liquid 3 5.0 parts of the compound (x2), 4.0 parts of the dispersant (BYKLPN-6919 manufactured by BYK), 4.0 parts of the resin (B-1) (in terms of solid content), 87 parts of propylene glycol monomethyl ether acetate was mixed, 300 parts of 0.4 mm zirconia beads were added and shaken for 1 hour using a paint conditioner (manufactured by LAU). Thereafter, the zirconia beads were removed by filtration to obtain Dispersion Liquid 3.
  • a paint conditioner manufactured by LAU
  • each component is as follows.
  • Latent antioxidant (E-1): GPA-5001 (manufactured by ADEKA, molecular weight 1578) (in terms of solid content)
  • each of the colored curable compositions of Examples and Comparative Examples was applied by spin coating so that the film thickness after post-baking was 0.8 ⁇ m, and then pre-baked at 80° C. for 2 minutes. to obtain a colored composition layer.
  • the substrate on which the colored composition layer was formed was irradiated with light at an exposure amount of 300 mJ/cm 2 (365 nm standard) using an exposure machine (NSR-1755i7A; manufactured by Nikon Corporation). A photomask on which a 2.0 ⁇ m square dot pattern was formed was used.
  • the colored composition layer after light irradiation is immersed in an aqueous developer containing tetramethylammonium hydroxide for 30 seconds at 23 ° C. After washing, the substrate after development (before post-baking) is post-baked at 230 ° C. for 10 minutes. , to obtain a colored pattern I after post-baking. Further, after storing the colored curable compositions of Example 1 and Comparative Example 1 at 40° C. for 3 days, post-baked colored pattern II was obtained in the same manner as described above. After storing the colored curable composition of Example 2 at 40° C. for one day, a post-baked colored pattern II was obtained in the same manner as described above.

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014021023A1 (ja) * 2012-07-31 2014-02-06 株式会社Adeka 潜在性添加剤及び該添加剤を含有する組成物
JP2016075837A (ja) * 2014-10-08 2016-05-12 東洋インキＳｃホールディングス株式会社 カラーフィルタ用着色組成物及びカラーフィルタ
JP2017008219A (ja) * 2015-06-23 2017-01-12 株式会社Adeka 組成物
WO2017030005A1 (ja) * 2015-08-17 2017-02-23 株式会社Adeka 組成物
JP2020052071A (ja) * 2018-09-21 2020-04-02 東洋インキＳｃホールディングス株式会社 カラーフィルタ用感光性着色組成物及びカラーフィルタ
JP2021092614A (ja) * 2019-12-06 2021-06-17 東洋インキＳｃホールディングス株式会社 感光性緑色組成物、カラーフィルタおよび表示装置

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JP2018091916A (ja) 2016-11-30 2018-06-14 東洋インキＳｃホールディングス株式会社 カラーフィルタ用着色組成物及びカラーフィルタ

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014021023A1 (ja) * 2012-07-31 2014-02-06 株式会社Adeka 潜在性添加剤及び該添加剤を含有する組成物
JP2016075837A (ja) * 2014-10-08 2016-05-12 東洋インキＳｃホールディングス株式会社 カラーフィルタ用着色組成物及びカラーフィルタ
JP2017008219A (ja) * 2015-06-23 2017-01-12 株式会社Adeka 組成物
WO2017030005A1 (ja) * 2015-08-17 2017-02-23 株式会社Adeka 組成物
JP2020052071A (ja) * 2018-09-21 2020-04-02 東洋インキＳｃホールディングス株式会社 カラーフィルタ用感光性着色組成物及びカラーフィルタ
JP2021092614A (ja) * 2019-12-06 2021-06-17 東洋インキＳｃホールディングス株式会社 感光性緑色組成物、カラーフィルタおよび表示装置

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