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WO2023140048A1 - Composition colorante - Google Patents

Composition colorante Download PDF

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Publication number
WO2023140048A1
WO2023140048A1 PCT/JP2022/047618 JP2022047618W WO2023140048A1 WO 2023140048 A1 WO2023140048 A1 WO 2023140048A1 JP 2022047618 W JP2022047618 W JP 2022047618W WO 2023140048 A1 WO2023140048 A1 WO 2023140048A1
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Prior art keywords
group
compound
formula
carbon atoms
hydrocarbon group
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PCT/JP2022/047618
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English (en)
Japanese (ja)
Inventor
拓磨 青木
智博 中山
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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Priority to CN202280089195.4A priority Critical patent/CN118715290A/zh
Priority to KR1020247026799A priority patent/KR20240135797A/ko
Publication of WO2023140048A1 publication Critical patent/WO2023140048A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
    • C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
    • C08F290/12—Polymers provided for in subclasses C08C or C08F
    • C08F290/126—Polymers of unsaturated carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/10—Acylation
    • 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
    • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • C09B47/10—Obtaining compounds having halogen atoms directly bound to the phthalocyanine skeleton
    • 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
    • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • C09B47/12—Obtaining compounds having alkyl radicals, or alkyl radicals substituted by hetero atoms, bound to the phthalocyanine skeleton
    • 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
    • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • C09B47/18—Obtaining compounds having oxygen atoms directly bound to the phthalocyanine skeleton
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/006—Preparation of organic pigments
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0084—Dispersions of dyes
    • C09B67/0085—Non common dispersing agents
    • C09B67/009—Non common dispersing agents polymeric dispersing agent
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10F—INORGANIC SEMICONDUCTOR DEVICES SENSITIVE TO INFRARED RADIATION, LIGHT, ELECTROMAGNETIC RADIATION OF SHORTER WAVELENGTH OR CORPUSCULAR RADIATION
    • H10F39/00—Integrated devices, or assemblies of multiple devices, comprising at least one element covered by group H10F30/00, e.g. radiation detectors comprising photodiode arrays
    • H10F39/80—Constructional details of image sensors
    • H10F39/805—Coatings
    • H10F39/8053—Colour filters
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/30—Devices specially adapted for multicolour light emission
    • H10K59/38—Devices specially adapted for multicolour light emission comprising colour filters or colour changing media [CCM]

Definitions

  • the present invention relates to a coloring composition, a color filter formed from the coloring composition, and a display device including the color filter.
  • 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 compositions.
  • Phthalocyanine pigments such as aluminum phthalocyanine pigments are known as colorants for such colored compositions (Patent Document 1).
  • an object of the present invention is to provide a coloring composition having good filterability.
  • the present invention includes the following inventions. [1] containing a coloring agent, a compound represented by formula (PI), a binder resin, and an organic solvent, the coloring agent comprises a phthalocyanine pigment, A coloring composition in which the compound represented by the formula (PI) has a molecular weight of 100 to 700.
  • Z p1 and Z p2 each independently represent a single bond or an oxygen atom.
  • R p1 represents an optionally substituted aliphatic unsaturated hydrocarbon group having 2 to 20 carbon atoms.
  • R p2 represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 20 carbon atoms, or a single bond connecting Z p2 and R p1 .
  • R a1 to R a5 and R a13 to R a14 each independently represent a hydrogen atom, a hydroxy group, an optionally substituted hydrocarbon group having 1 to 20 carbon atoms, or an optionally substituted heterocyclic group having 1 to 20 carbon atoms, and 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 , a halogen atom or a nitro group.
  • R x4 represents an optionally substituted hydrocarbon group having 1 to 20 carbon atoms, and when the hydrocarbon group has 2 to 20 carbon atoms and the hydrocarbon group has —CH 2 —, 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 heterocyclic group having 1 to 20 carbon atoms, 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 the hydrocarbon group has --CH.sub.2-- , the --CH.sub.2-- may be replaced with --O--, --S-- or --CO--.
  • 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 , a halogen atom or a nitro group.
  • R x5 represents an optionally substituted hydrocarbon group having 1 to 20 carbon atoms, and when the hydrocarbon group has 2 to 20 carbon atoms and the hydrocarbon group has —CH 2 —, 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; ]
  • [6] A color filter formed from the colored composition according to any one of [1] to [5].
  • [7] A display device including the color filter of [6].
  • a coloring composition with good filterability can be provided.
  • the present invention includes a coloring composition containing a coloring agent (hereinafter sometimes referred to as coloring agent (A)), a compound represented by formula (PI) (hereinafter sometimes referred to as compound (PI)), a binder resin (hereinafter sometimes referred to as binder resin (B)), and an organic solvent (hereinafter sometimes referred to as organic solvent (E)), wherein the coloring agent (A) contains a phthalocyanine pigment, and the compound (PI) has a molecular weight of 100 to 700.
  • coloring agent (A) a coloring agent
  • PI compound represented by formula
  • binder resin hereinafter sometimes referred to as binder resin (B)
  • organic solvent (E) organic solvent
  • the coloring composition of the present invention may contain a polymerizable compound (hereinafter sometimes referred to as a polymerizable compound (C)) and a polymerization initiator (hereinafter sometimes referred to as a polymerization initiator (D)).
  • the coloring composition of the present invention may contain a leveling agent (hereinafter sometimes referred to as leveling agent (F)).
  • leveling agent hereinafter sometimes referred to as leveling agent (F)
  • the compounds exemplified as each component can be used singly or in combination unless otherwise specified.
  • the coloring composition according to the present invention contains a phthalocyanine pigment as a coloring agent.
  • a phthalocyanine pigment include compounds represented by the following formulas (X1) to (X3).
  • the present invention will be described more specifically with partial structures of the compounds represented by formulas (X1) to (X3). Definitions common to Formula (Xa), Formula (Xb), Formula (X0), Formula (XI), Formula (XII), Formula (YI) or Formula (YII) will be described later.
  • 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 , a halogen atom or a nitro group.
  • R x4 represents an optionally substituted hydrocarbon group having 1 to 20 carbon atoms, and when the hydrocarbon group has 2 to 20 carbon atoms and the hydrocarbon group has —CH 2 —, 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;
  • M 1 represents a metal atom, a metal oxide, a metal hydroxide, a metal halide, a phosphorus-containing group-bonded metal, a silicon-containing group-bonded metal, an oxycarbonyl-containing group-bonded metal, or an oxysulfonyl-containing group-bonded metal.
  • X x1 to X x4 and nx1 to nx4 are the same as above.
  • M 2 and M 3 each independently represent a metal atom, metal oxide, metal hydroxide, or metal halide.
  • 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 heterocyclic group having 1 to 20 carbon atoms, 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.
  • 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 , a halogen atom or a nitro group.
  • R x5 represents an optionally substituted hydrocarbon group having 1 to 20 carbon atoms, and when the hydrocarbon group has 2 to 20 carbon atoms and the hydrocarbon group has —CH 2 —, the —CH 2 — may be replaced with —O—, —S— or —CO—.
  • Q + represents + N(R X17 ) 4 or an alkali metal ion, and 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; ]
  • M 1 to M 3 As a metal atom represented by M 1 to M 3 , specifically, Li, NA, K, TI, ZR, V, V, TA, TA, CR, MO, W, MN, MN, FE, CO, NI, RU, RU, Ru, RU, PD, PT, PT, CU, ZN, ZN, Zn CD, HG, AL, GA, IN, SI, GE, SN, PB, SB, BI, etc. are listed. Among them, Cu, Ni, Zn, or Al is particularly preferable.
  • metal oxides represented by M 1 to M 3 specifically, VO, GeO and the like are preferably mentioned.
  • Specific preferred metal hydroxides represented by M 1 to M 3 include AlOH, Si(OH) 2 , Cr(OH) 2 and Sn(OH) 2 .
  • metal halides represented by M 1 to M 3 include AlCl, SiCl 2 , VCl, VCl 2 , VOCl, FeCl, GaCl and ZrCl.
  • the phosphorus-containing group-bonded metal represented by M 1 has a structure in which a group containing a phosphorus atom is bonded to a metal atom, and the metal atom to which the phosphorus-containing group is bonded includes those described as the metal atoms represented by M 1 to M 3 above.
  • the silicon-containing group-bonded metal represented by M 1 has a structure in which a silicon-containing group is bonded to a metal atom, and examples of the metal atom to which the silicon-containing group is bonded include those described as the metal atoms represented by M 1 to M 3 above.
  • the silicon-containing group is preferably a group represented by --O--SiR a3 R a4 R a5 .
  • the oxysulfonyl-containing group-bonded metal represented by M 1 has a structure in which an oxysulfonyl-containing group is bonded to a metal atom, and examples of the metal atom to which the oxysulfonyl-containing group is bonded include those described as the metal atoms represented by M 1 to M 3 above.
  • M 1 is Cu, Ni, Zn or Al; oxides thereof; hydroxides thereof; halides thereof; structures in which phosphorus-containing groups are bonded; structures in which silicon-containing groups are bonded; Cu ; Ni ; Zn ; Al ; AlOH ; AlCl; ZrCl ; is more preferable.
  • M 2 and M 3 may be the same or different, but are preferably the same.
  • M 2 and M 3 are each independently preferably Cu, Ni, Zn or Al; oxides thereof; hydroxides thereof; halides thereof; More preferably, they are Cu, Ni, Zn or Al each independently.
  • the phthalocyanine pigment contained as the coloring agent of the present invention is preferably an aluminum phthalocyanine pigment, specifically a compound represented by formula (Xa) or formula (Xb).
  • R a1 to R a5 and R a13 to R a14 each independently represent a hydrogen atom, a hydroxy group, an optionally substituted hydrocarbon group having 1 to 20 carbon atoms, or an optionally substituted heterocyclic group having 1 to 20 carbon atoms, and any two of R a1 and R a2 or R a3 to R a5 may combine with each other to form a ring.
  • 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). Moreover, the compound represented by the formula (Xb) is preferably a compound represented by the formula (XII).
  • R x1 represents an optionally substituted C 2-20 aliphatic unsaturated hydrocarbon group or an optionally substituted C 6-20 aromatic hydrocarbon group.
  • 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 pigment is also preferably a compound 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.
  • Xy1 to Xy4 each independently represent -Ry4 , -ORy4 , -SRy4 , -SO3H , -SO3 - M + , -SO3Ry10 , -SO2NRy11Ry12 , a halogen 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.
  • Xy5 to Xy12 each independently represent -Ry5 , -ORy5 , -SRy5 , -SO3H , -SO3 - W + , -SO3Ry14 , -SO2NRy15Ry16 , a halogen 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 having an equilibrium relationship represented by formula (YIb), and the compound represented by formula (YII) includes a compound having a resonance structure represented by formula (YIIa) or a compound having an equilibrium relationship represented by formula (YIIb).
  • 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 number of carbon atoms in the aliphatic unsaturated hydrocarbon group represented by R x1 and R x3 is 2 to 20, more preferably 2 to 15, still more preferably 2 to 10, still more preferably 2 to 7, 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 a 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 a 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
  • 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 have substituents, heterocyclic groups which may have substituents, halogen atoms, nitro groups, cyano groups, —OR xa1 , —CO 2 R xa1 , —SR xa1 , —SO 3 R xa1 and —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.
  • R xa1 and R xa2 are the same as the hydrocarbon groups having 1 to 20 carbon atoms represented by R b1 to R b3 , R x2 , R x4 , R x5 and R y1 to R y5 described later.
  • R xa1 and R xa2 are each independently preferably a hydrogen atom, a linear or branched alkyl group having 1 to 10 carbon atoms, or an aromatic hydrocarbon group having 6 to 15 carbon atoms.
  • 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 15 carbon atoms, more preferably 6 to 10 carbon atoms, and still more preferably 6 to 8 carbon atoms.
  • the aromatic hydrocarbon group may have a substituent, and examples of the substituent include halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom and an iodine 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 (with the proviso that R xa1 and R xa2 are the same as above).
  • the heterocyclic group used as a substituent of the aliphatic unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by R x1 and R x3 may be monocyclic or polycyclic, and is preferably a heterocyclic ring containing a heteroatom as a ring constituent. Heteroatoms include nitrogen, oxygen and sulfur atoms.
  • Heterocyclic rings containing only a nitrogen atom as a heteroatom include monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine and piperazine; 5-membered ring unsaturated heterocycles such as pyrrole, pyrazole, imidazole, 1,2,3-triazole and 1,2,4-triazole; 6-membered ring unsaturated heterocycles such as pyridine, pyridazine, pyrimidine, pyrazine and 1,3,5-triazine; condensed bicyclic heterocycles such as sol, indoline, isoindoline, isoindoline-1,3-dione, indole, indolizine, benzimidazole, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole,
  • Heterocyclic rings containing a nitrogen atom and an oxygen atom as heteroatoms include monocyclic saturated heterocycles such as morpholine, 2-pyrrolidone and 2-piperidone; monocyclic unsaturated heterocycles such as oxazole and isoxazole; condensed bicyclic heterocycles such as benzoxazole, benzisoxazole, benzoxazine, benzodioxane and benzimidazoline; condensed tricyclic heterocycles such as phenoxazine; Heterocyclic rings containing a nitrogen atom and a sulfur atom as heteroatoms include monocyclic heterocyclic rings such as thiazole; condensed bicyclic heterocyclic rings such as benzothiazole; condensed tricyclic heterocyclic rings such as phenothiazine;
  • 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 15 carbon atoms, more preferably 6 to 10 carbon atoms, and still more preferably 6 to 8 carbon atoms.
  • Examples of the aromatic hydrocarbon group represented by R x1 and R x3 include the aromatic hydrocarbon groups exemplified as the aromatic hydrocarbon group having 6 to 20 carbon atoms used as a substituent for the aliphatic unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by R x1 and R x3 .
  • 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 atom, chlorine atom, bromine atom and iodine atom, 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 and the like. (provided that R xa1 and R xa2 are the same as above).
  • the hydrocarbon groups represented by R a1 to R a14 , 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 have 1 to 20 carbon atoms, more preferably 1 to 15 carbon atoms.
  • the hydrocarbon groups having 1 to 20 carbon atoms represented by R a1 to R a14 , 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 may be aliphatic hydrocarbon groups and aromatic hydrocarbon groups.
  • the aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or cyclic (alicyclic hydrocarbon group).
  • saturated or unsaturated chain hydrocarbon groups include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group and n-o.
  • linear alkyl groups such as a ktadecyl group, n-nonadecyl group, and n-icosyl 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-ethylpropyl 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-ethylhe
  • the number of carbon atoms in the saturated chain hydrocarbon group is preferably 1 to 15, more preferably 1 to 10, still more preferably 1 to 7, and particularly preferably 1 to 5.
  • the number of carbon atoms in the unsaturated chain hydrocarbon group is preferably 2 to 15, more preferably 2 to 10, still more preferably 2 to 7, and particularly preferably 2 to 5.
  • the saturated or unsaturated alicyclic hydrocarbon group includes a 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 and 2,3-dimethylcyclohexyl group.
  • xyl group 2,4-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4-dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group, 2,2-dimethylcyclohexyl group, 3,3-dimethylcyclohexyl group, 4,4-dimethylcyclohexyl group, cyclooctyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6,6-tetramethylcyclohexyl group Cycloalkyl groups such as a hexyl group, a 3,3,5,5-tetramethylcyclohexyl group, a 4-pentylcyclohexyl group, a 4-octylcyclohexyl group and a 4-cyclohexylcyclohexyl group; Cycloalkenyl groups such as a cyclohe
  • the aromatic hydrocarbon group examples include the aromatic hydrocarbon groups exemplified as the aromatic hydrocarbon group 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 .
  • the aromatic hydrocarbon group preferably has 6 to 20 carbon atoms, more preferably 6 to 15 carbon atoms, still more preferably 6 to 10 carbon atoms, and particularly preferably 6 to 8 carbon atoms.
  • the hydrocarbon groups represented by R a1 to R a14 , 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 are the above-mentioned hydrocarbon groups (e.g., aromatic hydrocarbon groups, aromatic hydrocarbon groups, chain at least one of a hydrocarbon group and an alicyclic hydrocarbon group) may be a combination of 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)phen
  • the —CH 2 — may be replaced with —O—, —S— or —CO—.
  • adjacent —CH 2 — are not simultaneously replaced with —O— and/or —S—, and —CH 2 — at the end of the compound is not replaced with —O—, —S— or —CO—.
  • *-O-CH 2 -CH 2 -CH 3 group is a group in which -CH 2 - in a hydrocarbon group having 4 carbon atoms (*-CH 2 -CH 2 -CH 2 -CH 3 ) is replaced with -O-.
  • —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 (*--CH 2 --CH 2 --CH 2 --CH 3 ) can be replaced with --O-- to form *--O--CH 2 --O--CH 3 .
  • a group such as *-O-CH 2 -O-CH 3 in which two or more -CH 2 - are replaced with -O-, -S- or -CO- is also included in "a group in which -CH 2 - in an optionally substituted hydrocarbon group having 1 to 20 carbon atoms is replaced with -O-, -S- or -CO-".
  • the substituents of the hydrocarbon groups having 1 to 20 carbon atoms represented by R a1 to R a14 , R b1 to R b3 , R x2 , R x4 , R x5 , R x11 , R x12 , R x15 , R x16 , R y1 to R y5 , R y11 , R y12 , R y15 and R y16 optionally have a hetero substituent.
  • the heterocyclic group used as a substituent of the hydrocarbon group having 1 to 20 carbon atoms represented by R a1 to R a14 , R b1 to R b3 , R x2 , R x4 , R x5 , R x11 , R x12 , R x15 , R x16 , R y1 to R y5 , R y11 , R y12 , R y15 and R y16 is monocyclic. It may be polycyclic, preferably a heterocyclic ring containing a heteroatom as a ring constituent. 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 atoms used as substituents of hydrocarbon groups having 1 to 20 carbon atoms represented by R a1 to R a14 , R b1 to R b3 , R x2 , R x4 , R x5 , R x11 , R x12 , R x15 , R x16 , R y1 to R y5 , R y11 , R y12 , R y15 and R y16 are fluorine atom, chlorine Atom, bromine atom, iodine atom and the like are exemplified.
  • 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 x11 to R x13 , R x15 to R x17 , R y1 to R y5 , R y11 to R y13 and R
  • the hydrocarbon groups represented by y15 to Ry17 the groups exemplified as linear alkyl groups, branched alkyl groups, cycloalkyl groups and saturated polycyclic hydrocarbon groups can be mentioned.
  • the heterocyclic groups having 1 to 20 carbon atoms represented by R a1 to R a14 may be monocyclic or polycyclic, and are preferably heterocyclic rings containing heteroatoms as ring constituents. 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 , —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 same).
  • the bonding position of the heterocyclic ring is a portion from which any hydrogen atom contained in each ring is eliminated.
  • a covalent bond corresponds to a single bond represented by R x2 .
  • R x1 is an optionally substituted aliphatic unsaturated hydrocarbon group having 2 to 20 carbon atoms
  • a ring formed by part or all of R x1 together with *—Z x2 —P( O)—Z x1 —* (* represents a bond)
  • an unsaturated bond may be formed between carbon atoms that are members of the ring
  • an unsaturated bond may be formed between a carbon atom that is a member of the ring and a carbon atom that is not a member of the ring
  • the ring Unsaturated bonds may be formed between carbon atoms that are not members of .
  • the halogen atoms represented by X x1 to X x12 and X y1 to X y12 include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably at least one selected from the group consisting of a fluorine atom, a chlorine atom and a bromine atom, more preferably a fluorine atom.
  • —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 and —R y5 represented by X y5 to X y12 are preferably aliphatic hydrocarbon groups having 1 to 20 carbon atoms, more preferably saturated chain hydrocarbon groups having 1 to 20 carbon atoms, more preferably saturated chain hydrocarbon groups having 1 to 10 carbon atoms.
  • a linear or branched alkyl group having numbers 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 more preferably a hydrogen atom or a saturated chain hydrocarbon group having 1 to 20 carbon atoms, more preferably a hydrogen atom or a saturated chain hydrocarbon group having 1 to 10 carbon atoms, and even more preferably a hydrogen atom or a saturated chain hydrocarbon group having 1 to 5 carbon atoms.
  • 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, more preferably a linear alkyl group having 1 to 10 carbon atoms.
  • R x11 , R x12 , R x15 , R x16 , R y11 , R y12 , R y15 and R y16 are each independently more preferably a hydrogen atom or a saturated chain hydrocarbon group having 1 to 20 carbon atoms, more preferably a hydrogen atom or a saturated chain hydrocarbon group having 1 to 10 carbon atoms, and even more preferably a hydrogen atom or a saturated chain hydrocarbon group having 1 to 5 carbon atoms.
  • R x1 is An optionally substituted unsaturated chain hydrocarbon group having 2 to 15 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 15 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 10 carbon atoms is more preferable, A phenyl group optionally having substituents, an ethenyl group optionally having substituents, a propenyl group optionally having substituents, a butenyl group optionally having substituents, a 3-methyl-2-butenyl group optionally having substituents, a 3-methyl-1,2-butadienyl group optionally having substituents, a heptenyl group optionally having substituents, an ethynyl group optionally having substituents, a propynyl group optionally having substituents , optionally substituted butynyl group, optionally substituted pent
  • R x1 is a substituted aliphatic unsaturated hydrocarbon group having 2 to 20 carbon atoms
  • the substituent is preferably an optionally substituted aromatic hydrocarbon group having 6 to 10 carbon atoms, more preferably a phenyl group.
  • Rx2 is A hydrogen atom, an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms, an optionally substituted unsaturated chain hydrocarbon group having 2 to 20 carbon atoms, an optionally substituted arylalkenyl group having 8 to 20 carbon atoms, an arylalkynyl group having an optionally substituted carbon number of 8 to 20, or a single bond connecting Z x2 and R x1 are preferred,
  • a hydrogen atom, an optionally substituted C6-10 aromatic hydrocarbon group, an optionally substituted C2-10 unsaturated chain hydrocarbon group, an optionally substituted C8-12 arylalkenyl group, an optionally substituted C8-12 arylalkynyl group, or a single bond connecting Z x2 and R x1 is more preferred,
  • X x1 to X x4 are each independently preferably -R x4 or a halogen atom, more preferably a saturated chain hydrocarbon group having 1 to 10 carbon atoms or a halogen atom, and particularly preferably a linear or branched alkyl group having 1 to 5 carbon atoms, a fluorine atom, a chlorine atom, or a bromine atom.
  • nx1 to nx4 are each independently preferably 0 to 2, more preferably 0 to 1, still more preferably 0.
  • R x3 is An unsaturated chain hydrocarbon group having 2 to 15 carbon atoms which may have a substituent is preferred, An unsaturated chain hydrocarbon group having 2 to 10 carbon atoms which may have a substituent is more preferable, An ethenyl group optionally having substituents, a propenyl group optionally having substituents, a butenyl group optionally having substituents, an ethynyl group optionally having substituents, a propynyl group optionally having substituents, or a butynyl group optionally having substituents are particularly preferable.
  • R x3 is a substituted aliphatic unsaturated hydrocarbon group having 2 to 20 carbon atoms
  • the substituent is preferably an optionally substituted 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 saturated chain hydrocarbon group having 1 to 10 carbon atoms or a halogen atom, and particularly preferably a linear or branched alkyl group having 1 to 5 carbon atoms, a fluorine atom, a chlorine atom, or a bromine atom.
  • nx5 to nx12 are each independently preferably 0 to 2, more preferably 0 to 1, still more preferably 0.
  • the phthalocyanine pigment contained as the coloring agent of the present invention is It is preferably at least one selected from the group consisting of a compound represented by formula (X1), a compound represented by formula (X2) and a compound represented by formula (X3), C. a compound represented by formula (Xa), a compound represented by formula (Xb), a compound represented by formula (YI), a compound represented by formula (YII); I. Pigment Blue 15, C.I. I. Pigment Blue 15:1, C.I. I. Pigment Blue 15:2, C.I. I. Pigment Blue 15:3, C.I. I. Pigment Blue 15:4, C.I. I. Pigment Blue 15:6, C.I. I. Pigment Blue 16, C.I. I.
  • Pigment Green 7 C.I. I. Pigment Green 36, C.I. I. Pigment Green 58, C.I. I. Pigment Green 59, C.I. I. Pigment Green 62, and C.I. I. It is more preferably at least one selected from the group consisting of Pigment Green 63, It is more preferably at least one selected from the group consisting of the compound represented by formula (X0), the compound represented by formula (XI), and the compound represented by formula (XII).
  • Compounds represented by formula (XIA) include, for example, Nos. Compounds having groups shown in 1-274 can be mentioned.
  • formula (XIA) No. Compounds having groups shown in 1 to 274 are respectively referred to as compounds (XIA-1) to (XIA-274).
  • Examples of compounds represented by formula (XIB) include No. Compounds having groups shown in 1-274 can be mentioned.
  • formula (XIB) No. Compounds having groups shown in 1 to 274 are referred to as compound (XIB-1) to compound (XIB-274), respectively.
  • Examples of compounds represented by the formula (XIC) include No. Compounds having groups shown in 1-274 can be mentioned.
  • Examples of compounds represented by the formula (XIF) include No. Compounds having groups shown in 1-274 can be mentioned.
  • No. Compounds having groups shown in 1 to 274 are referred to as compound (XIF-1) to compound (XIF-274), respectively.
  • the symbols described in the “R x1 ” and “R x2 ” columns in Tables 1 to 3 and 5 correspond to groups represented by formulas (xi-1) to (xi-22) and formulas (xii-1) to (xii-2), respectively.
  • R x1 and R x2 column in Table 4 correspond to the groups represented by formulas (xca-1) to (xca-2), formula (xcb-1), and formula (xcc-1), respectively.
  • R x6 and R x7 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 8) which may have a substituent
  • the hydrocarbon groups 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 .
  • Compound (XIA-1) ⁇ Compound (XIA-12), Compound (XIA-91) ⁇ Compound (XIA-102), Compound (XIA-103) ⁇ Compound (XIA-108), Compound (XIA-115) ⁇ Compound (XIA-119), Compound (XIA-126) ⁇ Compound (XIA-129), Compound (XIA-136) ⁇ Compound (XIA A-138), compound (XIA-145) to compound (XIA-146), compound (XIA-153), compound (IA-166), compound (XIA-181) to compound (XIA-200), compound (XIA-211) to compound (XIA-272) are preferred, Compound (XIA-1) ⁇ Compound (XIA-12), Compound (XIA-96), Compound (XIA-103) ⁇ Compound (XIA-105), Compound (XIA-115) ⁇ Compound (XIA-
  • Compound (XIC-1) ⁇ Compound (XIC-12), Compound (XIC-91) ⁇ Compound (XIC-102), Compound (XIC-103) ⁇ Compound (XIC-108), Compound (XIC-115) ⁇ Compound (XIC-119), Compound (XIC-126) ⁇ Compound (XIC-129), Compound (XIC-136) ⁇ Compound (XIC-138), Compound (XIC- 145) ⁇ Compound (XIC-146), Compound (XIC-153), Compound (XIC-181) ⁇ Compound (XIC-200), Compound (XIC-211) ⁇ Compound (XIC-272) are preferred, Compound (XIC-1) to compound (XIC-12), compound (XIC-103) to compound (XIC-105), compound (XIC-115) to compound (XIC-116), and compound (XIC-126) are more preferred.
  • Compounds represented by formula (XIIA) include, for example, No. Compounds having groups shown in 1 to 18 can be mentioned.
  • formula (XIIA) No. Compounds having groups shown in 1 to 18 are referred to as compound (XIIA-1) to compound (XIIA-18), respectively.
  • Compounds represented by formula (XIIB) include, for example, No. Compounds having groups shown in 1 to 18 can be mentioned.
  • formula (XIIB) No. Compounds having groups shown in 1 to 18 are referred to as compound (XIIB-1) to compound (XIIB-18), respectively.
  • Compounds represented by formula (XIIC) include, for example, No.
  • Compounds having groups shown in 1 to 18 are referred to as compound (XIIE-1) to compound (XIIE-18), respectively.
  • Compounds represented by formula (XIIF) include, for example, No. Compounds having groups shown in 1 to 18 can be mentioned.
  • formula (XIIF) No. Compounds having groups shown in 1 to 18 are referred to as compound (XIIF-1) to compound (XIIF-18), respectively.
  • the symbols described in the “R x3 ” column in Table 6 correspond to the groups represented by formulas (xiii-1) to (xiii-9). * represents a bond.
  • compound (XIIA-1) to compound (XIIA-6) and compound (XIIA-10) to compound (XIIA-15) are preferred.
  • compound (XIIB-1) to compound (XIIB-6) and compound (XIIB-10) to compound (XIIB-15) are preferred.
  • compound (XIIC-1) to compound (XIIC-6) and compound (XIIC-10) to compound (XIIC-15) are preferred.
  • compound (XIID-1) to compound (XIID-6) and compound (XIID-10) to compound (XIID-15) are preferred.
  • compound (XIIE-1) to compound (XIIE-6) and compound (XIIE-10) to compound (XIIE-15) are preferred.
  • compound (XIIF-1) to compound (XIIF-6) and compound (XIIF-10) to compound (XIIF-15) are preferred.
  • 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 produced, for example, by appropriately reacting a compound represented by formula (XIII-1), a compound represented by formula (XIII-2), 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 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.
  • ny1 to ny4 are each independently 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.
  • At least one of Y 1 , Z y1 , Z y2 and Z y3 represents a sulfur atom, and preferably satisfies at least one aspect among the aspect in which Y 1 is a sulfur atom and Z y1 is an oxygen atom, the aspect in which Y 1 is an oxygen atom and Z y1 is a sulfur atom, and the aspect in which Z y2 and Z y3 are sulfur atoms.
  • R y2 is an unsaturated aliphatic hydrocarbon group
  • Z y2 and Z y3 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 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 saturated chain hydrocarbon group having 1 to 10 carbon atoms or a halogen atom, and particularly preferably a straight or branched chain alkyl group having 1 to 5 carbon atoms, a fluorine atom, a chlorine atom or a bromine atom. 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 compounds represented by formula (YIA) include No. Compounds having groups shown in 1 to 24 can be mentioned.
  • the formula (YIA) No. Compounds having groups shown in 1 to 24 are respectively referred to as compound (YIA-1) to compound (YIA-24).
  • Examples of compounds represented by the formula (YIB) include No. Compounds having groups shown in 1 to 24 can be mentioned.
  • the formula (YIB) No. Compounds having groups shown in 1 to 24 are respectively referred to as compound (YIB-1) to compound (YIB-24).
  • Compounds represented by the formula (YIC) include, for example, No. Compounds having groups shown in 1 to 24 can be mentioned.
  • the formula (YIC) No.
  • Compound (YIA-1) ⁇ compound (YIA-6), compound (YIA-13) ⁇ compound (YIA-18), compound (YIA-21), compound (YIA-22) ⁇ compound (YIA-24) are preferred, Compound (YIA-1), compound (YIA-13), compound (YIA-21), compound (YIA-23) and compound (YIA-24) are more preferred.
  • Compound (YIB-1) ⁇ compound (YIB-6), compound (YIB-13) ⁇ compound (YIB-18), compound (YIB-21), compound (YIB-22) ⁇ compound (YIB-24) are preferred, Compound (YIB-1), compound (YIB-13), compound (YIB-21), compound (YIB-23) and compound (YIB-24) are more preferred.
  • Compound (YIC-1) ⁇ compound (YIC-6), compound (YIC-13) ⁇ compound (YIC-18), compound (YIC-21), compound (YIC-22) ⁇ compound (YIC-24) are preferred, Compound (YIC-1), compound (YIC-13), compound (YIC-21), compound (YIC-23) and compound (YIC-24) are more preferred.
  • Compound (YID-1) ⁇ compound (YID-6), compound (YID-13) ⁇ compound (YID-18), compound (YID-21), compound (YID-22) ⁇ compound (YID-24) are preferred, Compound (YID-1), compound (YID-13), compound (YID-21), compound (YID-23) and compound (YID-24) are more preferred.
  • Compound (YIE-1) ⁇ compound (YIE-6), compound (YIE-13) ⁇ compound (YIE-18), compound (YIE-21), compound (YIE-22) ⁇ compound (YIE-24) are preferred, Compound (YIE-1), compound (YIE-13), compound (YIE-21), compound (YIE-23) and compound (YIE-24) are more preferred.
  • Compounds represented by formula (YII) include compounds represented by formulas (YIIA) to (YIIE).
  • Examples of compounds represented by the formula (YIIA) include No. Compounds having groups shown in 1 to 13 can be mentioned.
  • the formula (YIIA) No. Compounds having groups shown in 1 to 13 are respectively referred to as compound (YIIA-1) to compound (YIIA-13).
  • Examples of compounds represented by the formula (YIIB) include No. Compounds having groups shown in 1 to 13 can be mentioned.
  • formula (YIIB) No. Compounds having groups shown in 1 to 13 are respectively referred to as compound (YIIB-1) to compound (YIIB-13).
  • Examples of compounds represented by the formula (YIIC) include No. Compounds having groups shown in 1 to 13 can be mentioned.
  • Compound (YIIA-1), compound (YIIA-2), compound (YIIA-8), compound (YIIA-9), compound (YIIA-12), compound (YIIA-13) are preferred, Compound (YIIA-1), compound (YIIA-8), compound (YIIA-12) and compound (YIIA-13) are more preferred.
  • Compound (YIIB-1), compound (YIIB-2), compound (YIIB-8), compound (YIIB-9), compound (YIIB-12), compound (YIIB-13) are preferred, Compound (YIIB-1), compound (YIIB-8), compound (YIIB-12) and compound (YIIB-13) are more preferred.
  • Compound (YIIC) As the compound represented by the formula (YIIC), Compound (YIIC-1), Compound (YIIC-2), Compound (YIIC-8), Compound (YIIC-9), Compound (YIIC-12), Compound (YIIC-13) are preferred, Compound (YIIC-1), compound (YIIC-8), compound (YIIC-12) and compound (YIIC-13) are more preferable.
  • Compound (YIID-1), compound (YIID-2), compound (YIID-8), compound (YIID-9), compound (YIID-12), compound (YIID-13) are preferred, Compound (YIID-1), compound (YIID-8), compound (YIID-12) and compound (YIID-13) are more preferred.
  • Compound (YIIE) As the compound represented by the formula (YIIE), Compound (YIIE-1), Compound (YIIE-2), Compound (YIIE-8), Compound (YIIE-9), Compound (YIIE-12), Compound (YIIE-13) are preferred, Compound (YIIE-1), compound (YIIE-8), compound (YIIE-12) and compound (YIIE-13) are more preferable.
  • 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 content of the phthalocyanine pigment is preferably 20% by mass or more, more preferably 50% by mass or more, and still more preferably 70% by mass or more, and may be 100% by mass or 90% by mass or less in the total amount of the colorant (A).
  • the content of the aluminum phthalocyanine pigment is preferably 20 to 100% by mass, more preferably 30 to 100% by mass, and still more preferably 40 to 100% by mass in the total amount of the phthalocyanine pigment.
  • the coloring agent (A) may further contain a coloring agent different from the phthalocyanine pigment (hereinafter sometimes referred to as coloring agent (A2)).
  • the coloring agent (A2) may be either a dye or a pigment.
  • 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 Dye Note (Shikisensha). Xanthene dyes are particularly preferred.
  • a xanthene dye is a dye that contains a compound with a xanthene skeleton in its molecule.
  • xanthene dyes include C.I. I. Acid Red 51 (hereinafter, the description of CI Acid Red is omitted and only the number is described. The same applies to others.), 52, 87, 92, 94, 289, 388, C.I. I. Acid Violet 9, 30, 102, C.I. I. Basic Red 1 (Rhodamine 6G), 2, 3, 4, 8, 10, 11, C.I. I. Basic Violet 10 (Rhodamine B), 11, C.I. I. Solvent Red 218, C.I. I. Mordan Tread 27, C.I. I.
  • Reactive Red 36 (Rose Bengal B), sulforhodamine G, xanthene dyes described in JP-A-2010-32999 and xanthene dyes described in Japanese Patent No. 4492760, and the like. Those soluble in organic solvents are preferred.
  • xanthene dyes commercially available xanthene dyes (for example, "Chugai Aminol Fast Pink R-H/C” manufactured by Chugai Kasei Co., Ltd., “Rhodamin 6G” manufactured by Taoka Chemical Co., Ltd.) can be used. Moreover, it is also possible to synthesize a commercially available xanthene dye as a starting material with reference to JP-A-2010-32999.
  • dyes that may be used include azo dyes, cyanine dyes, triphenylmethane dyes, thiazole dyes, oxazine dyes, phthalocyanine dyes, quinophthalone dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, and nitro dyes.
  • Specific examples of such dyes include C.I. I. Solvent Yellow 4 (hereinafter, the description of C.I. Solvent Yellow is omitted and only the number is described.
  • Solvent Blue 4 5, 14, 18, 35, 36, 37, 45, 58, 59, 59: 1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; C. I. C.I. I. solvent dyes, C. I.
  • pigments examples include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists), and the following pigments can be exemplified.
  • 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.
  • Purple pigment C.I. I. Pigment Violet 1, 19, 23, 29, 32, 36, 38, etc.
  • one kind of pigment or a plurality of pigments may be used for each color, and pigments of each color may be combined.
  • the pigment may be subjected, if necessary, to rosin treatment, surface treatment using a pigment derivative into which an acidic group or basic group is introduced, graft treatment on the pigment surface with a polymer compound, etc., atomization treatment by a sulfuric acid atomization method or the like, washing treatment with an organic solvent or water to remove impurities, removal treatment by an ion exchange method for ionic impurities, or the like. It is preferable that the particle size of the pigment is substantially uniform.
  • the pigment can be dispersed uniformly in the pigment dispersant solution by adding a pigment dispersant to the pigment and dispersing the pigment.
  • the pigments may be dispersed individually, or may be mixed and dispersed.
  • 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 pigment dispersants may be used alone or in combination of two or more.
  • pigment dispersants examples include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA (registered trademark) (manufactured by BASF), Ajisper (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark), and BYK (registered trademark) (manufactured by BYK-Chemie). .
  • 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 20 parts by mass or more and 160 parts by mass or less, relative to 100 parts by mass of the pigment.
  • the amount of the pigment dispersant used is within the above range, there is a tendency to obtain a pigment dispersion in a more uniformly dispersed state when two or more pigments are used.
  • the content of the colorant (A2) is preferably 1 to 80% by mass, more preferably 1 to 50% by mass, and still more preferably 1 to 30% by mass, based on the total amount of the colorant (A).
  • the content of the coloring agent (A) in the coloring composition is preferably 0.5 to 80% by mass, more preferably 1 to 70% by mass, more preferably 2 to 55% by mass, particularly preferably 8 to 50% by mass, based on the total amount of solids.
  • the term "total amount of solids” refers to the total amount of components of the coloring 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 coloring composition according to the present invention contains compound (PI). By containing the compound (PI), filterability is improved.
  • Z p1 and Z p2 each independently represent a single bond or an oxygen atom.
  • R p1 represents an optionally substituted aliphatic unsaturated hydrocarbon group having 2 to 20 carbon atoms.
  • R p2 represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 20 carbon atoms, or a single bond connecting Z p2 and R p1 .
  • Examples of the unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms represented by R p1 include the groups described in the unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms represented by R x1 and R x3 , that is, unsaturated chain hydrocarbon groups such as alkenyl groups and alkynyl groups, cycloalkenyl groups, and unsaturated alicyclic hydrocarbon groups such as unsaturated polycyclic hydrocarbon groups.
  • the aliphatic unsaturated hydrocarbon group preferably has 2 to 15 carbon atoms, more preferably 2 to 10 carbon atoms, still more preferably 2 to 7 carbon atoms, and particularly preferably 2 to 5 carbon atoms.
  • Examples of the hydrocarbon group having 1 to 20 carbon atoms represented by R p2 include the same groups as the hydrocarbon groups having 1 to 20 carbon atoms represented by R a1 . That is, the hydrocarbon group having 1 to 20 carbon atoms represented by R p2 includes chain hydrocarbon groups such as linear or branched alkyl groups, alkenyl groups and alkynyl groups; alicyclic hydrocarbon groups such as cycloalkyl groups, cycloalkenyl groups and saturated or unsaturated polycyclic hydrocarbon groups; aromatic hydrocarbon groups; a group in which a group and an alicyclic hydrocarbon group are combined; and the like. Moreover, in each group, the preferred embodiment of each carbon number is also the same.
  • Substituents which the unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms represented by R p1 may have include an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, 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 , etc. (provided that R xa1 and R xa2 are the same as above).
  • substituents which the hydrocarbon group having 1 to 20 carbon atoms represented by R p2 may have include heterocyclic groups which may have substituents, halogen atoms, nitro groups, cyano groups, —OR a1 , —CO 2 R xa1 , —SR xa1 , —SO 2 R xa1 , —SO 3 R xa1 , —SO 2 NR xa1 R xa2 and —NR xa1 R xa. 2 , etc. (provided that R xa1 and R xa2 are the same as above).
  • Examples of the aromatic hydrocarbon group used as a substituent of the unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms represented by R p1 include the aromatic hydrocarbon groups exemplified as the aromatic hydrocarbon groups having 6 to 20 carbon atoms which are used as a substituent of the aliphatic unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by R x1 and R x3 .
  • 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 , —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 the substituent of the aliphatic unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by R p1 and the substituent of the hydrocarbon group having 1 to 20 carbon atoms represented by R p2 may be monocyclic or polycyclic, and is preferably a heterocyclic ring containing a heteroatom as a ring constituent.
  • 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 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 2 R xa1 , —SO 3 R xa1 , —SO 2 NR xa1 R xa2 and —NR xa1 R xa2 (provided that R xa1 and R xa2 are same as ).
  • the bonding position of the heterocyclic ring is a portion from which any hydrogen atom contained in each ring is eliminated.
  • the halogen atom used as a substituent of the aliphatic unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by R p1 and a substituent of the hydrocarbon group having 1 to 20 carbon atoms represented by R p2 is exemplified by fluorine atom, chlorine atom, bromine atom and iodine atom.
  • R p2 may be a single bond connecting Z p2 and R p1 .
  • R p2 is a single bond connecting Z p2 and R p1 , part or all of R p1 is combined with *—Z p2 —P( ⁇ O)—Z p1 —* (* represents a bond) to form a ring. That is, when R p2 is a single bond connecting Z p2 and R p1 , a bond formed by sharing a pair of electrons between any carbon atom in the optionally substituted aliphatic unsaturated hydrocarbon group having 2 to 20 carbon atoms represented by R p1 and Z p2 corresponds to the single bond represented by R p2 .
  • an unsaturated bond may be formed between carbon atoms that are members of the ring, an unsaturated bond may be formed between a carbon atom that is a member of the ring and a carbon atom that is not a member of the ring, or an unsaturated bond may be formed between carbon atoms that are not members of the ring.
  • An unsaturated chain hydrocarbon group having 2 to 10 carbon atoms which may have a substituent is preferred, Ethenyl group optionally having substituents, propenyl group optionally having substituents, butenyl group optionally having substituents, 3-methyl-2-butenyl group optionally having substituents, 3-methyl-1,2-butadienyl group optionally having substituents, heptenyl group optionally having substituents, ethynyl group optionally having substituents, propynyl group optionally having substituents, butynyl group optionally having substituents Nyl group, optionally substituted pentynyl group, optionally substituted 1-methyl-3-butynyl group, optionally substituted 1,1-dimethyl-2-propynyl group, optionally substituted hexynyl group, optionally substituted 1-ethyl-3-butynyl group, optionally substituted heptynyl group, optionally substituted
  • the substituent is preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, more preferably a phenyl group.
  • a hydrogen atom, an optionally substituted C6-C20 aromatic hydrocarbon group, an optionally substituted C2-C20 aliphatic unsaturated hydrocarbon group, an optionally substituted C8-C20 arylalkenyl group, an optionally substituted C8-C20 arylalkynyl group, or a single bond connecting Z p2 and R p1 is preferred,
  • a hydrogen atom, an optionally substituted C6-10 aromatic hydrocarbon group, an optionally substituted C2-10 unsaturated chain hydrocarbon group, an optionally substituted C8-15 arylalkenyl group, an optionally substituted C8-15 arylalkynyl group, or a single bond connecting Z p2 and R p1 is more preferred,
  • the molecular weight of the compound (PI) is 100 or more and 700 or less, preferably 120 or more, more preferably 140 or more, and preferably 500 or less, more preferably 300 or less. When the molecular weight of the compound (PI) is within the above range, it becomes easier to obtain a colored composition with good filterability.
  • the content of the compound (PI) is, for example, 1 part by mass or more, preferably 3 parts by mass or more, more preferably 5 parts by mass or more, still more preferably 10 parts by mass or more, and preferably 30 parts by mass or less, more preferably 25 parts by mass or less, and still more preferably 20 parts by mass or less, relative to 100 parts by mass of the phthalocyanine pigment.
  • the content of the compound (PI) is preferably 0.5% by mass or more, more preferably 1.0% by mass or more, still more preferably 2.0% by mass or more, and preferably 5.0% by mass or less, more preferably 4.0% by mass or less, and still more preferably 3.0% by mass or less, relative to the total amount of solids.
  • the binder resin (B) is not particularly limited, it is preferably an alkali-soluble resin.
  • the binder resin (B) include the following resins [K1] to [K6].
  • Resin [K1] a copolymer of 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 monomer (b) having a cyclic ether structure with 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b)”);
  • 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; Unsaturated dicarboxylic acids such as 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, dimethyltetrahydrophthalic acid, 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-ethylbic
  • (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 (b2) (hereinafter sometimes referred to as “(b2)”), and a monomer having a tetrahydrofuryl group and an ethylenically unsaturated bond (b3) (hereinafter sometimes referred to as "(b3)").
  • a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond hereinafter sometimes referred to as "(b1)
  • b2 monomer having an oxetanyl group and an ethylenically unsaturated bond
  • (b3) a monomer having a tetrahydrofuryl group and an ethylenically unsaturated bond
  • (b1) includes, for example, a monomer (b1-1) having a structure in which a linear or branched unsaturated aliphatic hydrocarbon is epoxidized (hereinafter sometimes 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(glycidyl 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)sty
  • (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), and 3,4-epoxytricyclohexane.
  • [5.2.1.0 2,6 ]decyl (meth)acrylate compounds represented by formula (R1), compounds represented by formula (R2), and the like.
  • 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 may be 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 a hydrogen atom is substituted with hydroxy include a 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.
  • alkanediyl group examples include methylene group, ethylene group, propane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group and the like.
  • X ra and X rb preferably include 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, compounds represented by formula (R1-1), formula (R1-3), formula (R1-5), formula (R1-7), formula (R1-9) or formulas (R1-11) to formula (R1-15) are preferred, and compounds represented by formula (R1-1), formula (R1-7), formula (R1-9) or formula (R1-15) are more preferred.
  • Examples of the compound represented by formula (R2) include compounds represented by any one of formulas (R2-1) to (R2-15). Among them, compounds represented by formula (R2-1), formula (R2-3), formula (R2-5), formula (R2-7), formula (R2-9) or formulas (R2-11) to formula (R2-15) are preferred, and compounds represented by formula (R2-1), formula (R2-7), formula (R2-9) or formula (R2-15) are more preferred.
  • (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, and 3-ethyl-3-methacryloyloxyethyl oxetane, 3-ethyl-3-acryloyloxyethyl oxetane and the like.
  • (b3) is more preferably a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group.
  • Specific examples of (b3) include tetrahydrofurfuryl acrylate (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 terms of excellent storage stability of the coloring composition.
  • (c) is preferably 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, etc. 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 coloring composition, the developability when forming a colored pattern, and the solvent resistance of the resulting color filter tend to be excellent.
  • the resin [K1] can be produced, for example, by referring to the method described in the document "Experimental Methods for Polymer Synthesis” (written by Takayuki Otsu, Published by Kagaku Dojin, 1st Edition, 1st Edition, published on March 1, 1972) and the references cited therein.
  • a method of putting predetermined amounts of (a) and (b), a polymerization initiator, a solvent, etc. into a reaction vessel and, for example, replacing oxygen with nitrogen to create a deoxygenated atmosphere and heating and keeping the temperature while stirring is not particularly limited, and those commonly used in the relevant field can be used.
  • the polymerization initiator includes azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.).
  • the obtained copolymer may be used as a solution after the reaction, as a concentrated or diluted solution, or as a solid (powder) taken out by a method such as reprecipitation.
  • a solution after the reaction as a concentrated or diluted solution, or as a solid (powder) taken out by a method such as reprecipitation.
  • an organic solvent contained in the coloring composition as a solvent during the polymerization, the solution after the reaction can be used as it is for the preparation of the coloring composition, so that the manufacturing process of the coloring composition 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 ratio of the structural units of the resin [K2] is within the above range, the storage stability of the colored composition, the developability when forming a colored pattern, and the solvent resistance, heat resistance, and mechanical strength of the obtained color filter tend to be excellent.
  • 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] can be produced by obtaining a copolymer of (a) and (c) and adding a cyclic ether having 2 to 4 carbon atoms of (b) to the carboxylic acid and/or carboxylic anhydride of (a).
  • a copolymer of (a) and (c) is produced in the same manner as the method for producing resin [K1].
  • 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, (b), a reaction catalyst (e.g., tris(dimethylaminomethyl)phenol, triphenylphosphine, etc.) and a polymerization inhibitor (e.g., hydroquinone, methoquinone, etc.) between a carboxylic acid or a carboxylic acid anhydride and a cyclic ether are placed in the flask and reacted at, for example, 60 to 130° C.
  • a reaction catalyst e.g., tris(dimethylaminomethyl)phenol, triphenylphosphine, etc.
  • a polymerization inhibitor e.g., hydroquinone, methoquinone, etc.
  • the amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, per 100 mol of (a). Within this range, the storage stability of the coloring composition, the developability when forming a pattern, and the solvent resistance, heat resistance, mechanical strength and sensitivity balance of the resulting pattern tend to be good. Since the cyclic ether has high reactivity and unreacted (b) hardly remains, (b1) is preferable as the (b) used for the resin [K4], and (b1-1) is more preferable.
  • the amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass 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 it is after the reaction, may be used as a concentrated or diluted solution, or may be taken out as a solid (powder) by a method such as reprecipitation.
  • 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.
  • resin [K5] can be obtained by reacting the cyclic ether derived from (b) in the copolymer of (b) and (c) with the carboxylic acid or carboxylic anhydride of (a) under the same conditions as in the method for producing resin [K4].
  • 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, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride and the like.
  • the amount of carboxylic acid anhydride to be used is preferably 0.1 to 1 mol per 1 mol of (a).
  • the polystyrene-equivalent weight average molecular weight of the binder 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 binder resin (B) is preferably 1.1-6, more preferably 1.2-4.
  • the acid value of the binder resin (B) is preferably 10 to 170 mg-KOH/g, more preferably 20 to 150 mg-KOH/g, still more preferably 30 to 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 binder resin (B), and can be determined, for example, by titration using an aqueous potassium hydroxide solution.
  • the content of the binder 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 17 to 55% by mass, relative to the total solid content.
  • the content of the binder resin (B) is within the above range, a colored pattern can be formed, and the resolution and residual film rate of the colored pattern 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). Examples thereof include compounds having a polymerizable ethylenically unsaturated bond, preferably (meth)acrylic acid ester compounds.
  • the polymerizable compound (C) is preferably a polymerizable compound having 3 or more ethylenically unsaturated bonds.
  • examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tris (2-(Meth)acryloyloxyethyl)isocyanurate, ethylene glycol-modified (also
  • Pentaerythritol tetra(meth)acrylate ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified (also referred to as propylene oxide-modified. Same below.) Pentaerythritol tetra(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, caprolactone-modified dipenta erythritol hexa(meth)acrylate and the like.
  • the number of moles of EO added to the ethylene oxide modified product and the number of moles of PO added to the propylene oxide modified product are preferably 5 to 30.
  • the trimethylol props (meta) acrylate (meta) acrylate (meta) acrylate (meta) acrylate, dipenta lithritol hexa (meta) acrylate, ethylene oxide degenerative gypaine lythol hexa (meta) Acrylate (meta) Acrylate is preferable.
  • 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 13 to 60% by mass, and still more preferably 17 to 55% by mass, relative to the total amount of solids.
  • 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 not particularly limited as long as it is a compound capable of initiating polymerization by generating active radicals, acids, etc. by the action of light or heat, and known polymerization initiators can be used.
  • Examples of polymerization initiators that generate active radicals include alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds and biimidazole compounds.
  • the O-acyloxime compound is a compound having a partial structure represented by formula (d1). Below, * represents a bond.
  • O-acyloxime compounds examples include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6 -(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6- ⁇ 2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl ⁇ -9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)
  • O-acyloxime compounds include N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine and N-benzoyloxy-1-(4-phenylsulfanylphenyl )-3-cyclopentylpropan-1-one-2-imine is preferred, and N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexy
  • the alkylphenone compound is preferably 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, and the like.
  • Commercially available products such as Irgacure 369, 907 and 379 (manufactured by BASF) may also be used.
  • Examples of compounds having a partial structure represented by formula (d3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexylphenylketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, ⁇ , ⁇ -diethoxyacetophenone, and benzyldimethylketal. etc.
  • the alkylphenone compound is preferably a compound having a partial structure represented by formula (d2).
  • triazine compounds 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-methoxystyryl)-1, 3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-tri
  • 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(dialkoxy
  • JP-B-48-38403, JP-A-62-174204, etc. biimidazole compounds in which the phenyl group at the 4,4'5,5'-position is substituted with a carboalkoxy group (see, for example, JP-A-7-10913).
  • the polymerization initiator (D) includes benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone;9, quinone compounds such as 10-phenanthrenequinone, 2-ethylanthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, titanocene compounds and the like. These are preferably used in combination with a polymerization initiation aid (D1) (especially a
  • polymerization initiators that generate acids include onium salts such as 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetoxyphenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, and diphenyliodonium hexafluoroantimonate, nitrobenzyl tosylates, benzoin tosylates and the like.
  • onium salts such as 4-hydroxyphenyldimethylsulfonium p-
  • a polymerization initiator containing at least one selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound and a biimidazole compound is preferred, and a polymerization initiator containing an O-acyloxime compound is more preferred.
  • 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 binder resin (B) and the polymerizable compound (C).
  • 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 compounds examples include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl paratoluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis ( diethylamino)benzophenone, 4,4'-bis(ethylmethylamino)benzophenone and the like, with 4,4'-bis(diethylamino)benzophenone being preferred.
  • 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-dibutoxyanthracene, and 2-ethyl-9,10-dibutoxyanthracene.
  • thioxanthone compounds examples include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.
  • carboxylic acid compound examples include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid, and the like.
  • the content thereof is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass with respect to the total amount of 100 parts by mass of the binder resin (B) and the polymerizable compound (C).
  • 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.
  • Organic solvent (E) is not particularly limited, and solvents commonly used in this field can be used.
  • solvents commonly used in this field can be used.
  • ester solvents solvents containing -COO- in the molecule and not containing -O-
  • ether solvents solvents containing -O- in the molecule but not containing -COO-
  • ether ester solvents solvents containing -COO- and -O- in the molecule
  • ketone solvents solvents containing -CO- in the molecule and not containing -COO-
  • alcohol solvents solvents containing OH in the molecule and not containing -O-, -CO- and -COO-
  • aromatic hydrocarbons solvents, amide solvents, dimethyl sulfoxide and the like can be mentioned.
  • 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, 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, and diethylene glycol diethyl. ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetol and methylanisole.
  • Ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, 2 methyl-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 monoethyl
  • Ketone solvents include 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone and isophorone.
  • Alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol and glycerin.
  • Aromatic hydrocarbon solvents include benzene, toluene, xylene and mesitylene.
  • Amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidone.
  • the organic solvent (E) is preferably one or more selected from the group consisting of ether solvents, ether ester solvents, ketone solvents and amide solvents, and more preferably contains one or more selected from the group consisting of diethylene glycol methyl ethyl ether, propylene glycol monomethyl ether acetate, diacetone alcohol, and N-methylpyrrolidone. Among them, it preferably contains an ether solvent and/or an ether ester solvent (especially an ether ester solvent), and more preferably contains an ether solvent/or an ether ester solvent and a ketone solvent.
  • the mass ratio (ether solvent/ether ester solvent) is, for example, 5/95 to 50/50, preferably 10/90 to 30/70.
  • the content of the ketone solvent is, for example, 0.1 to 15 parts by mass, preferably 1 to 10 parts by mass, with respect to the total of 100 parts by mass of the ether solvent and the ether ester solvent.
  • the content of the organic solvent (E) is preferably 70-95% by mass, more preferably 75-92% by mass, relative to the total amount of the coloring composition.
  • the solids content of the coloring composition is preferably 5-30% by weight, more preferably 8-25% by weight.
  • 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 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 (Shin-Etsu Chemical Co., Ltd. Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (manufactured by Momentive Performance Materials Japan LLC).
  • fluorine-based surfactants examples include surfactants having a fluorocarbon chain in the molecule.
  • Florado registered trademark
  • FC430 Florado (registered trademark) FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megafac (registered trademark) F142D, Florado (registered trademark) F171, Florado F172, Florado F173, Flora F177, Flora F183, Flora F554, Flora R30, Flora de RS-718-K (manufactured by DIC Corporation), Ftop (registered trademark) EF301 and EF303 , EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, S382, SC101, SC105 (AGC Co., Ltd. (former Asahi Glass Co., Ltd.)) and E5844 (manufactured by Daikin Fine Chemical
  • 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, and still more preferably 0.005 to 0.05% by mass, relative to the total amount of the coloring composition. This content does not include the content of the pigment dispersant.
  • the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.
  • the coloring composition may optionally contain additives known in the art such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents, and the like.
  • the coloring composition can be prepared by, for example, mixing a coloring agent (A) containing a phthalocyanine pigment, a compound (PI), a binder resin (B), an organic solvent (E), and optionally a polymerizable compound (C), a polymerization initiator (D), a leveling agent (F), a polymerization initiation aid (D1) and other components.
  • a coloring agent (A) containing a phthalocyanine pigment a compound (PI), a binder resin (B), an organic solvent (E), and optionally a polymerizable compound (C), a polymerization initiator (D), a leveling agent (F), a polymerization initiation aid (D1) and other components.
  • the phthalocyanine pigment may be included in the pigment dispersion in advance.
  • the pigment dispersion liquid preferably contains a part or all of the phthalocyanine pigment, the compound (PI), the binder resin (B), and the organic solvent (E).
  • the pigment dispersion contains a phthalocyanine pigment, compound (PI), binder resin (B), and organic solvent (E)
  • the pigment dispersion is also included in the coloring composition of the present invention.
  • a desired colored composition can also be prepared by mixing such a pigment dispersion with the remaining components so as to have a predetermined concentration.
  • the content of the phthalocyanine pigment is preferably 15% by mass or more, more preferably 20% by mass or more, still more preferably 30% by mass or more, and preferably 90% by mass or less, more preferably 80% by mass or less, and still more preferably 70% by mass or less, relative to the total solid content of the pigment dispersion.
  • the content of the compound (PI) is preferably 1.0% by mass or more, more preferably 2.0% by mass or more, still more preferably 3.0% by mass or more, and preferably 30% by mass or less, more preferably 20% by mass or less, and still more preferably 10% by mass or less, relative to the total solid content of the pigment dispersion.
  • the content of the binder resin (B) is preferably 7.0% by mass or more, more preferably 13% by mass or more, still more preferably 17% by mass or more, and preferably 65% by mass or less, more preferably 60% by mass or less, and still more preferably 55% by mass or less, relative to the total solid content of the pigment dispersion.
  • the content of the organic solvent (E) in the pigment dispersion is preferably 70% by mass or more, more preferably 75% by mass or more, and is preferably 95% by mass or less, more preferably 92% by mass or less.
  • the dye may be dissolved in part or all of the organic solvent (E) 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.
  • Examples of the method for producing a colored pattern of a color filter from the colored composition of the present invention include a photolithography method, an inkjet method, a printing method and the like.
  • the photolithographic method is preferred.
  • the photolithographic method is a method in which the coloring composition is applied to a substrate, dried to form a composition layer, exposed through a photomask, and developed.
  • 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 film thickness of the color filter (cured 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, particularly preferably 0.5 ⁇ m or less, preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more, and even more preferably 0.3 ⁇ m or more.
  • a glass plate such as quartz glass, borosilicate glass, alumina silicate glass, soda lime glass whose surface is coated with silica, a resin plate such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, silicon, or a substrate having aluminum, silver, or silver/copper/palladium alloy thin film formed thereon is used.
  • a resin plate such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, silicon, or a substrate having aluminum, silver, or silver/copper/palladium alloy thin film formed thereon is used.
  • Other color filter layers, resin layers, transistors, circuits, and the like may be formed on these substrates.
  • 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 device and conditions. For example, it can be produced as follows. First, the coloring 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 may be cut using a filter that cuts this wavelength range, or light near 436 nm, 408 nm, and 365 nm may be selectively extracted using a band-pass filter that extracts these wavelength ranges.
  • mercury lamps, light-emitting diodes, metal halide lamps, halogen lamps and the like can be used.
  • a reduction projection exposure apparatus such as a mask aligner and a stepper or a proximity exposure apparatus because it is possible to uniformly irradiate the entire exposure surface with parallel rays and to perform accurate alignment between the photomask and the substrate.
  • 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 color filters, and the color filters are useful as color filters used in display devices (e.g., liquid crystal display devices, organic EL devices, etc.), electronic paper, solid-state imaging devices, and the like.
  • the structure of the compound was confirmed by mass spectrometry (MALDI-TOF MS; JEOL JMS-S3000).
  • Synthesis example 1 1.0 parts of the compound represented by the formula (1) (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.32 parts of the compound represented by the formula (2) (“API-9” manufactured by Katayama Chemical Industries, Ltd.), and N-methylpyrrolidone (hereinafter also referred to as NMP) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) 10.0 parts were mixed at room temperature, heated to 120 ° C. and stirred for 6 hours. After cooling the reaction solution to room temperature, 50 parts of ion-exchanged water was added. The resulting precipitate was collected as a residue of suction filtration, washed with 50 parts of methanol, and dried under reduced pressure while heating at 60° C. to obtain 0.98 parts of the compound represented by formula (3).
  • NMP N-methylpyrrolidone
  • Synthesis example 2 A compound represented by formula (4) was obtained by the synthesis method described in Supporting Information of Ryan B. Snitynsky et al "Synthesis of Nitrogen-Containing Furanose Sugar Nucleotides for Use as Enzymatic Probes" (Org. Lett. 2014, 16, 1, 212-215).
  • Synthesis example 3 In the synthesis method of the compound represented by Formula (4) in Synthesis Example 2, allyl alcohol was changed to 3-buten-1-ol to obtain a compound represented by Formula (6).
  • Synthesis example 4 A compound represented by Formula (8) was obtained by changing allyl alcohol to 3-butyn-1-ol in the method for synthesizing the compound represented by Formula (4) in Synthesis Example 2.
  • Synthesis example 5 To 1.8 parts of cis-2-butene-1,4-diol (manufactured by Tokyo Chemical Industry Co., Ltd.), 6.1 parts of triethylamine, and 200 parts of toluene (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), 6.1 parts of phosphoryl chloride was added dropwise at 0°C. After dropping, the mixture was heated to room temperature and stirred for 4.5 hours. After removing the triethylamine hydrochloride by filtering the reaction solution, the solvent was removed by a rotary evaporator.
  • Synthesis example 6 1.5 parts of aluminum chloride (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.), 6.2 parts of 4-tert-butyl phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.), 5.1 parts of 1,8-diazabicyclo[5.4.0]-7-undecene (manufactured by Tokyo Chemical Industry Co., Ltd.), and 11 parts of 1-pentanol (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.) are mixed at room temperature and heated to 160 ° C. Stirred for 13 hours. After cooling the reaction solution to room temperature, 63 parts of ethyl acetate was added. The resulting precipitate was collected as a residue of suction filtration, washed with 89 parts of ion-exchanged water, and dried at 60° C. under reduced pressure to obtain 3.4 parts of the compound represented by formula (12).
  • Synthesis example 7 A compound represented by formula (14) was synthesized according to [0071] to [0072] of PCT National Publication No. 2012-507743.
  • Synthesis example 8 1.6 parts of the compound represented by formula (14), 0.47 parts of the compound represented by formula (4), and 7.8 parts of NMP were mixed at room temperature, heated to 120°C, and stirred for 8 hours. After cooling the reaction solution to room temperature, 39 parts of ion-exchanged water was added. The resulting precipitate was collected as a residue of suction filtration and dried under reduced pressure at 60°C to obtain 1.9 parts of the compound represented by formula (16).
  • Synthesis example 9 A compound represented by formula (17) was synthesized in the same manner except that 4-fluorophthalonitrile of [0071] to [0072] was changed to 4,5-difluorophthalonitrile in PCT National Publication No. 2012-507743.
  • Synthesis example 10 A compound represented by formula (19) was synthesized according to the experimental section on page 651 of Tamara V. Basova et al “Molecular organization in the thin films of chloroaluminium hexadecafluorophthalocyanine revealed by polarized Raman spectroscopy” (Thin Solid Films, 2013, Volume 548, 650-656).
  • Synthesis Example 11 1.4 parts of the compound represented by the formula (19), 0.32 parts of the compound represented by the formula (4), and 14 parts of NMP were mixed at room temperature, heated to 120°C, and stirred for 7 hours. After cooling the reaction solution to room temperature, 70 parts of ion-exchanged water was added. The resulting precipitate was collected as a residue of suction filtration and dried under reduced pressure at 60° C. to obtain 1.5 parts of the compound represented by formula (21).
  • Synthesis Example 12 In the method for synthesizing the compound represented by formula (4) in Synthesis Example 2, allyl alcohol was changed to 2-propyn-1-ol to obtain a compound represented by formula (23).
  • Synthesis Example 13 A mixed solution of 2.10 parts of 3-butyn-1-ol (manufactured by Tokyo Chemical Industry Co., Ltd.) and 11.1 parts of tetrahydrofuran was dropped into 6.65 parts of phenyl dichlorophosphate (manufactured by Tokyo Chemical Industry Co., Ltd.) and 11.1 parts of tetrahydrofuran (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.). Subsequently, a mixed solution of 7.59 parts of triethylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) and 11.1 parts of tetrahydrofuran was added dropwise at 0°C.
  • Synthesis Example 14 A compound represented by Formula (27) was obtained by changing phenyl dichlorophosphate to phenylphosphonic acid dichloride in the method for synthesizing the compound represented by Formula (25) in Synthesis Example 13.
  • Synthesis example 15 1.0 parts of the compound represented by the formula (12), 0.51 parts of the compound represented by the formula (8), and 5.0 parts of NMP were mixed at room temperature, heated to 120°C, and stirred for 6 hours. After cooling the reaction solution to room temperature, 50 parts of ion-exchanged water was added. The resulting precipitate was collected as a residue of suction filtration and dried under reduced pressure at 60°C to obtain 0.94 parts of the compound represented by formula (29).
  • Synthesis Example 16 2.0 parts of the compound represented by formula (1), 0.75 parts of the compound represented by formula (30) (manufactured by Tokyo Kasei Kogyo Co., Ltd.), and 10.0 parts of NMP were mixed at room temperature, heated to 120° C. and stirred for 6 hours. After cooling the reaction solution to room temperature, 50 parts of ion-exchanged water was added. The resulting precipitate was collected as a residue of suction filtration and dried under reduced pressure at 60° C. to obtain 1.8 parts of a mixture of the compound represented by formula (31-I) and the compound represented by formula (31-II).
  • Synthesis Example 17 In the synthesis method of the compound represented by formula (4) in Synthesis Example 2, allyl alcohol was changed to 4-pentyn-2-ol to obtain a compound represented by formula (32).
  • Synthesis Example 18 A compound represented by Formula (34) was obtained by changing 3-butyn-1-ol to 4-pentyn-2-ol in the method for synthesizing the compound represented by Formula (25) in Synthesis Example 13.
  • Synthesis Example 19 In the method for synthesizing the compound represented by formula (4) in Synthesis Example 2, allyl alcohol was changed to 5-hexyn-3-ol to obtain a compound represented by formula (36).
  • Synthesis example 20 A compound represented by Formula (38) was obtained by changing 3-butyn-1-ol to 5-hexyn-3-ol in the method for synthesizing the compound represented by Formula (25) in Synthesis Example 13.
  • Synthesis example 21 In the synthesis method of the compound represented by Formula (4) in Synthesis Example 2, allyl alcohol was changed to 7-octin-1-ol to obtain a compound represented by Formula (40).
  • Synthesis example 22 In the synthesis method of the compound represented by Formula (4) in Synthesis Example 2, allyl alcohol was changed to 9-decyn-1-ol to obtain a compound represented by Formula (42).
  • Synthesis Example 23 In the synthesis method of the compound represented by formula (4) in Synthesis Example 2, allyl alcohol was changed to 5-heptyn-3-ol to obtain a compound represented by formula (44).
  • Synthesis example 24 In the method for synthesizing the compound represented by Formula (4) in Synthesis Example 2, allyl alcohol was changed to 3-pentyn-1-ol to obtain a compound represented by Formula (46).
  • Synthesis example 25 In the method for synthesizing the compound represented by formula (4) in Synthesis Example 2, allyl alcohol was changed to 5-hexyn-1-ol to obtain a compound represented by formula (48).
  • Synthesis example 26 A compound represented by the formula (50) was obtained by changing the allyl alcohol used to 6-hepsyn-1-ol in the method for synthesizing the compound represented by the formula (4) in Synthesis Example 2.
  • Synthesis Example 27 In the synthesis method of the compound represented by Formula (4) in Synthesis Example 2, allyl alcohol was changed to 2-octin-1-ol to obtain a compound represented by Formula (52).
  • Synthesis Example 28 A compound represented by Formula (54) was obtained by changing allyl alcohol to 3-phenyl-2-propyn-1-ol in the method for synthesizing the compound represented by Formula (4) in Synthesis Example 2.
  • Synthesis Example 29 In the method for synthesizing the compound represented by Formula (19) in Synthesis Example 10, tetrafluorophthalonitrile was changed to 4-bromophthalonitrile to obtain a compound represented by Formula (56).
  • Synthesis example 30 A compound represented by the formula (58) was obtained by the synthesis method described in JP-A-2016-75837.
  • Resin (B-1) has the following structural units.
  • Dispersion 1 4.4 parts of the compound represented by the formula (3) obtained in Synthesis Example 1, 0.65 parts of the compound represented by the formula (2), 4 parts of a dispersing agent (BYKLPN-6919 manufactured by BYK) (in terms of solid content), 4 parts of resin (B-1) (in terms of solid content), and 87 parts of propylene glycol monomethyl ether acetate are mixed, 300 parts of 0.2 ⁇ m zirconia beads are added, and a paint conditioner (LAU) is added. company) and shaken for 1 hour. After that, the zirconia beads were removed by filtration to obtain Dispersion Liquid 1.
  • a dispersing agent BYKLPN-6919 manufactured by BYK
  • resin B-1
  • LAU paint conditioner
  • dispersion liquid 2 (Preparation of dispersion liquid 2) C. I. 12.0 parts of Pigment Blue 15:4, 3.6 parts of dispersant (BYKLPN-6919 manufactured by BYK), 5.4 parts of resin (B-1) (in terms of solid content), 12.0 parts of diacetone alcohol, propylene glycol monomethyl ether acetate 67 parts were mixed, 300 parts of 0.4 mm zirconia beads were added, and the mixture was 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 4 4.4 parts of the compound represented by the formula (58) obtained in Synthesis Example 30, 0.18 parts of diphenyl phosphate (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 4 parts of a dispersant (BYKLPN-6919 manufactured by BYK) (in terms of solid content), 4 parts of resin (B-1) (in terms of solid content), and 87 parts of propylene glycol monomethyl ether acetate are mixed, 300 parts of 0.2 ⁇ m zirconia beads are added, and the mixture is painted. A conditioner (manufactured by LAU) was used and shaken for 1 hour. Thereafter, the zirconia beads were removed by filtration to obtain Dispersion Liquid 4.
  • a conditioner manufactured by LAU
  • Example 3 to 30 (Preparation of colored curable composition) Colored curable compositions 3 to 30 are prepared in the same manner as in Example 1, except that the compound represented by formula (3) used in the preparation of Dispersion 1 is changed to the following compound.
  • Example 3 Colored curable composition 2: Compound represented by formula (5) obtained in Synthesis Example 2
  • Example 4 Colored curable composition 3: Compound represented by Formula (7) obtained in Synthesis Example 3
  • Example 5 Colored curable composition 4: Compound represented by Formula (9) obtained in Synthesis Example 4
  • Example 6 Colored curable composition 5: Compound represented by Formula (11) obtained in Synthesis Example 5
  • Example 8 Colored curable composition 7: Compound represented by the formula (15) obtained in Synthesis Example 7
  • Example 9 Colored curable composition 8: Compound represented by the formula (16) obtained in Synthesis Example 8
  • Example 10 Colored curable composition 9: Compound represented by the formula (18) obtained in Synthesis Example 9
  • Example 12 Colored curable composition 11: Compound represented by formula (21) obtained in Synthesis Example 11
  • Example 13 Colored curable composition 12: Compound represented by formula (24) obtained in Synthesis Example 12

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Abstract

L'objectif de la présente invention est de fournir une composition colorante ayant une bonne filtrabilité. La présente invention concerne une composition colorante contenant un agent colorant, un composé représenté par la formule (PI), une résine liante et un solvant organique, l'agent colorant contenant un pigment phtalocyanine, et le poids moléculaire du composé représenté par la formule (PI) étant de 100 à 700. [Dans la formule (PI), Zp1 et Zp2 représentent chacun indépendamment une liaison simple ou un atome d'oxygène. Rp1 représente un groupe hydrocarboné aliphatique en C2-C20 qui peut avoir un substituant. Rp2 représente un atome d'hydrogène, un groupe hydrocarboné en C1-C10 qui peut avoir un substituant, ou une liaison simple reliant Zp2 et Rp1.]
PCT/JP2022/047618 2022-01-20 2022-12-23 Composition colorante Ceased WO2023140048A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6270454A (ja) * 1985-09-25 1987-03-31 Dainichi Color & Chem Mfg Co Ltd 顔料のフラッシング方法
JPS6354475A (ja) * 1986-04-04 1988-03-08 Toyo Alum Kk 水性塗料用アルミフレ−ク顔料組成物
JP2019105727A (ja) * 2017-12-12 2019-06-27 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剤、着色組成物およびカラーフィルタ
JP2020094121A (ja) * 2018-12-12 2020-06-18 東洋インキＳｃホールディングス株式会社 フタロシアニン顔料、着色組成物およびカラーフィルタ
WO2022024926A1 (fr) * 2020-07-31 2022-02-03 住友化学株式会社 Composés

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4311775A (en) * 1980-10-06 1982-01-19 Eastman Kodak Company Novel phthalocyanine pigments and electrophotographic uses thereof
US4704165A (en) * 1985-05-21 1987-11-03 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Pigment composition
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

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6270454A (ja) * 1985-09-25 1987-03-31 Dainichi Color & Chem Mfg Co Ltd 顔料のフラッシング方法
JPS6354475A (ja) * 1986-04-04 1988-03-08 Toyo Alum Kk 水性塗料用アルミフレ−ク顔料組成物
JP2019105727A (ja) * 2017-12-12 2019-06-27 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剤、着色組成物およびカラーフィルタ
JP2020094121A (ja) * 2018-12-12 2020-06-18 東洋インキＳｃホールディングス株式会社 フタロシアニン顔料、着色組成物およびカラーフィルタ
WO2022024926A1 (fr) * 2020-07-31 2022-02-03 住友化学株式会社 Composés

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