WO2022009526A1 - 着色組成物、膜、光学フィルタ、固体撮像素子、画像表示装置及び化合物 - Google Patents
着色組成物、膜、光学フィルタ、固体撮像素子、画像表示装置及び化合物 Download PDFInfo
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- WO2022009526A1 WO2022009526A1 PCT/JP2021/018694 JP2021018694W WO2022009526A1 WO 2022009526 A1 WO2022009526 A1 WO 2022009526A1 JP 2021018694 W JP2021018694 W JP 2021018694W WO 2022009526 A1 WO2022009526 A1 WO 2022009526A1
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- pigment
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/70—Microphotolithographic exposure; Apparatus therefor
- G03F7/708—Construction of apparatus, e.g. environment aspects, hygiene aspects or materials
- G03F7/7095—Materials, e.g. materials for housing, stage or other support having particular properties, e.g. weight, strength, conductivity, thermal expansion coefficient
- G03F7/70958—Optical materials or coatings, e.g. with particular transmittance, reflectance or anti-reflection properties
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/76—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/06—Zinc compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/10—Homopolymers or copolymers of methacrylic acid esters
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/08—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
- C08L67/025—Polyesters derived from dicarboxylic acids and dihydroxy compounds containing polyether sequences
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B55/00—Azomethine dyes
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- 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
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0042—Photosensitive materials with inorganic or organometallic light-sensitive compounds not otherwise provided for, e.g. inorganic resists
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0048—Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
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- 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
- H10F39/10—Integrated devices
- H10F39/12—Image sensors
- H10F39/15—Charge-coupled device [CCD] image sensors
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- 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
- H10F39/10—Integrated devices
- H10F39/12—Image sensors
- H10F39/18—Complementary metal-oxide-semiconductor [CMOS] image sensors; Photodiode array image sensors
Definitions
- the present invention relates to a coloring composition containing a pigment.
- the present invention also relates to a film using a coloring composition, an optical filter, a solid-state image sensor, an image display device, and a compound.
- color filters are used as key devices for displays and optical elements.
- a color filter usually includes pixels of the three primary colors of red, green, and blue, and plays a role of decomposing transmitted light into the three primary colors.
- Patent Document 1 describes a color using a pigment containing an azomethine metal complex pigment, a pigment derivative in which two sulfonic acid groups are introduced into the azomethine metal complex pigment, a resin, and a coloring composition containing a solvent. It is described to form the pixels of the filter.
- an object of the present invention is to provide a coloring composition capable of forming pixels having excellent developer resistance. Another object of the present invention is to provide a film, an optical filter, a solid-state image pickup device, an image display device, and a compound using a coloring composition.
- the resin P is a graft resin P-1 having a graft chain containing at least one structure selected from a polyester structure, a polyether structure and a poly (meth) acrylic structure.
- Coloring composition In formula (1), R 1 represents a hydrogen atom, an alkyl group or an aryl group, R 2 to R 9 independently represent a hydrogen atom or a substituent, and two adjacent groups of R 2 to R 9 are adjacent to each other.
- any one of R 2 to R 9 contains a group represented by the formula (R-1); -W 1- (X 1 ) n ... (R-1)
- W 1 represents a single bond or an n + 1 valent linking group
- X 1 represents an acid group or a basic group
- n represents an integer of 1-5; where W 1 is simply.
- n is 1.
- the acid group represented by X 1 in the above formula (R-1) is a carboxy group, a sulfo group, a phosphoric acid group, a group represented by ⁇ SO 2 NHSO 2 Rf 1 , or a salt thereof, and Rf.
- W 1 of the formula (R-1) is a single bond, X 1 is an acid group, and n is 1.
- M 1 represents a metal atom to which the ligand may be coordinated; where any one of R 2 to R 9 is the above formula (R-). Includes the group represented by 1).
- M 1 in the above formula (1a) is a copper atom to which the ligand may be coordinated or a zinc atom to which the ligand may be coordinated.
- ⁇ 8> The coloring composition according to any one of ⁇ 1> to ⁇ 7>, wherein the pigment contains at least one selected from a yellow pigment, a green pigment and a red pigment.
- ⁇ 9> The coloring composition according to any one of ⁇ 1> to ⁇ 8>, wherein the pigment contains a pigment having a metal atom.
- the pigment having a metal atom contains an azomethine metal complex.
- the azomethine metal complex contains at least one selected from an azomethine copper complex and an azomethine zinc complex.
- ⁇ 13> The coloring composition according to any one of ⁇ 1> to ⁇ 12>, further comprising a polymerizable compound and a photopolymerization initiator.
- ⁇ 14> The coloring composition according to any one of ⁇ 1> to ⁇ 13>, which is for a color filter or an infrared transmission filter.
- ⁇ 15> The coloring composition according to any one of ⁇ 1> to ⁇ 14>, which is for a solid-state image sensor.
- ⁇ 16> A film obtained from the coloring composition according to any one of ⁇ 1> to ⁇ 15>.
- ⁇ 17> An optical filter having the film according to ⁇ 16>.
- ⁇ 18> A solid-state image sensor having the film according to ⁇ 16>.
- R 2a ⁇ R 9a are each independently hydrogen atom, a salt of a carboxyl group, a salt of sulfo group, salts of the phosphate group, the group represented by -SO 2 NHSO 2 Rf 1, in -SO 2 NHSO 2 Rf 1 Salts of represented groups, halogen atoms, alkyl groups, alkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, cyano groups, hydroxy groups, nitro groups, alkoxy groups, aryloxy groups, silyloxy groups, heterocyclic oxy groups, Acyloxy group, carbamoyloxy group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, alkylsulfonylamino group, arylsulfonylamino group, mercapto group, alkylthio group, arylthi
- M 1a represents a metal atom to which the ligand may be coordinated; However, any one of R 2a ⁇ R 9a, salts of sulfo group, a group represented by -SO 2 NHSO 2 Rf 1, or is the salt of a group represented by -SO 2 NHSO 2 Rf 1;
- R 21a represents a hydrogen atom, an alkyl group or an aryl group.
- R 22a ⁇ R 31a are each independently hydrogen atom, a salt of a carboxyl group, a salt of sulfo group, salts of the phosphate group, the group represented by -SO 2 NHSO 2 Rf 1, in -SO 2 NHSO 2 Rf 1 Salts of represented groups, halogen atoms, alkyl groups, alkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, cyano groups, hydroxy groups, nitro groups, alkoxy groups, aryloxy groups, silyloxy groups, heterocyclic oxy groups, Acyloxy group, carbamoyloxy group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, alkylsulfonylamino group, arylsulfonylamino group, mercapto group, alkylthio group, arylthi
- M 2a represents a metal atom to which the ligand may be coordinated; However, any one of R 22a ⁇ R 31a, salts of sulfo group, a group represented by -SO 2 NHSO 2 Rf 1, or a salt of the group represented by -SO 2 NHSO 2 Rf 1.
- a coloring composition capable of forming pixels having excellent developer resistance, a film using the coloring composition, an optical filter, a solid-state image sensor, an image display device, and a compound.
- the contents of the present invention will be described in detail.
- "to” is used to mean that the numerical values described before and after it are included as the lower limit value and the upper limit value.
- the notation not describing substitution and non-substituent also includes a group having a substituent (atomic group) as well as a group having no substituent (atomic group).
- the "alkyl group” includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
- the term "exposure” includes not only exposure using light but also drawing using particle beams such as electron beams and ion beams, unless otherwise specified.
- Examples of the light used for exposure include the emission line spectrum of a mercury lamp, far ultraviolet rays typified by an excimer laser, extreme ultraviolet rays (EUV light), X-rays, active rays such as electron beams, or radiation.
- EUV light extreme ultraviolet rays
- (meth) acrylate” represents both acrylate and methacrylate, or either
- “(meth) acrylic” represents both acrylic and methacrylic, or either.
- Acryloyl "represents both acryloyl and / or methacryloyl.
- Me in the structural formula represents a methyl group
- Et represents an ethyl group
- Bu represents a butyl group
- Ph represents a phenyl group.
- the weight average molecular weight and the number average molecular weight are polystyrene-equivalent values measured by a GPC (gel permeation chromatography) method.
- the total solid content means the total mass of all the components of the composition excluding the solvent.
- the term pigment means a compound that is difficult to dissolve in a solvent.
- the term "process” is included in this term not only as an independent process but also as long as the intended action of the process is achieved even if it cannot be clearly distinguished from other processes. ..
- the symbol (for example, S) added before or after the name is a term used to distinguish the components, and the type of the component, the number of the components, and the structure are used. It does not limit the superiority or inferiority of the elements.
- the coloring composition of the present invention comprises at least one compound S selected from the compound S-1 represented by the formula (1) and the compound S-2 in which the compound S-1 is coordinated to a metal atom.
- the resin P is a graft resin P-1 having a graft chain containing at least one structure selected from a polyester structure, a polyether structure and a poly (meth) acrylic structure.
- the graft resin P-1 and the block copolymer P-2 and the resin P-3 are collectively referred to as a specific resin.
- the coloring composition of the present invention it is possible to form pixels having excellent developer resistance, in which the occurrence of pixel chipping due to the developer is suppressed.
- a pattern is formed by a photolithography method using a coloring composition to form pixels, it is possible to suppress the occurrence of pixel chipping due to a developing solution during development.
- an optical filter having pixels of a plurality of colors by sequentially forming pixels of each color using a coloring composition of a plurality of colors, when forming the pixels of the second and subsequent colors, in the step before that.
- the formed pixels are also exposed to the developing liquid, but by using the coloring composition of the present invention, it is possible to form pixels having excellent developer resistance, and therefore, before that, when forming the second and subsequent color pixels. It is possible to suppress damage caused by the developing solution of the pixels formed in the above, and it is possible to suppress the occurrence of chipping and the like. According to the coloring composition of the present invention, even when pixels having a fine line width of 1.0 ⁇ m or less (preferably 0.9 ⁇ m or less) are formed, pixels having excellent developer resistance are formed. Therefore, it is effective in forming pixels having a fine line width of 1.0 ⁇ m or less (preferably 0.9 ⁇ m or less).
- the coloring composition of the present invention also has a wide exposure latitude. Therefore, when a pattern is formed by a photolithography method using the coloring composition of the present invention, the allowable range of the exposure amount when forming pixels having a desired line width is wide, and therefore the photolithography is excellent. ..
- Compound S-1 has an aromatic ring and an azomethine structure, and it is presumed that compound S can form a strong intermolecular bond with the pigment. Further, by having a group represented by 1 Exemplary ethynylphenylbiadamantane derivatives (R-1) of the Compound S-1 R 2 ⁇ R 9 in the formula (1) representing the compound S Strong molecules and specific resin It is speculated that an intermolecular bond can be formed. As a result, it is presumed that a strong network of the pigment, the compound S and the above-mentioned specific resin is formed in the film.
- the compound S easily interacts with a pigment having a metal atom, and when a pigment having a metal atom is used, it is possible to form a pixel having more excellent developer resistance.
- a pigment having a metal atom when used, it is possible to form a pixel having more excellent developer resistance.
- an azomethine metal complex or a phthalocyanine metal complex is used as the pigment, a more excellent effect is exhibited.
- the coloring composition of the present invention is preferably used as a coloring composition for a color filter or an infrared transmission filter. More specifically, it can be preferably used as a coloring composition for forming pixels of a color filter or a coloring composition for forming an infrared transmission filter, and more preferably used as a coloring composition for forming pixels of a color filter. Further, the coloring composition of the present invention is preferably used for a solid-state image sensor. More specifically, it is preferably used as a coloring composition for forming pixels of a color filter used in a solid-state image sensor, or as a coloring composition for forming an infrared transmission filter.
- the wavelength at which the light transmittance of the film is 50% exists in the wavelength range of 470 to 520 nm to 475 to 725. It is more preferably present in the wavelength range of 520 nm, and even more preferably in the wavelength range of 480 to 520 nm. Above all, it is preferable that the wavelength at which the light transmittance is 50% exists in each of the wavelength range of 470 to 520 nm and the wavelength range of 575 to 625 nm.
- the wavelength on the short wavelength side where the light transmittance is 50% preferably exists in the wavelength range of 475 to 520 nm, and more preferably exists in the wavelength range of 480 to 520 nm. Further, the wavelength on the long wavelength side where the light transmittance is 50% preferably exists in the wavelength range of 580 to 620 nm, and more preferably exists in the wavelength range of 585 to 615 nm.
- a coloring composition capable of forming a film having such spectral characteristics is preferably used as a coloring composition for forming green pixels of a color filter.
- the coloring composition of the present invention contains a pigment.
- the average primary particle size of the pigment is preferably 1 to 200 nm.
- the lower limit is preferably 5 nm or more, more preferably 10 nm or more.
- the upper limit is preferably 180 nm or less, more preferably 150 nm or less, still more preferably 100 nm or less.
- the primary particle size of the pigment can be obtained from a photograph obtained by observing the primary particles of the pigment with a transmission electron microscope.
- the projected area of the primary particles of the pigment is obtained, and the corresponding circle-equivalent diameter is calculated as the primary particle diameter of the pigment.
- the average primary particle size in the present invention is an arithmetic average value of the primary particle size for the primary particles of 400 pigments.
- the primary particles of the pigment refer to independent particles without aggregation.
- the pigment examples include chromatic pigments and black pigments, and chromatic pigments are preferable.
- the pigment may be either an inorganic pigment or an organic pigment, but is preferably an organic pigment from the viewpoint of many color variations, ease of dispersion, safety and the like.
- the pigment is preferably a pigment having a metal atom, more preferably an organic pigment having a metal atom, and an azomethine metal complex, an azo metal complex and the like, because it is possible to form a pixel having better developer resistance. It is more preferably a phthalocyanine metal complex, further preferably an azomethine metal complex and a phthalocyanine metal complex, and particularly preferably an azomethine metal complex.
- the azomethine metal complex is preferably a yellow pigment. Further, the azomethin metal complex preferably contains at least one selected from the azomethin copper complex and the azomethin zinc complex, and more preferably contains the azomethin copper complex. Further, a dinuclear complex may be used as the azomethine metal complex.
- the azomethine metal complex may be used alone or in combination of two or more. When two or more kinds of azomethine metal complexes are used in combination, two or more kinds of azomethine metal complexes may form a mixed crystal (solid solution).
- C.I. I. Pigment Yellow 117, 129 and the like C. I. Pigment Yellow 117 is a compound represented by the following formula (ACu-2), and C.I. I. Pigment Yellow 129 is a compound represented by the following formula (ACu-1).
- the nitrogen atom is coordinated to the copper (Cu) atom, but the nitrogen atom may not be coordinated to the copper atom.
- a dinuclear complex may be used as the azomethin copper complex.
- Examples of the binuclear complex of the azomethin copper complex include a complex having a structure in which a quadrangle is formed by Cu—O and Cu—O.
- Examples of the azomethin zinc complex include a compound represented by the formula (AZn-1), a compound represented by the formula (AZn-2), and the like.
- the nitrogen atom is coordinated to the zinc (Zn) atom, but the nitrogen atom may not be coordinated to the zinc atom.
- X 1 and X 2 independently represent a hydrogen atom, a halogen atom or an alkoxy group, respectively.
- Examples of the halogen atom represented by X 1 and X 2 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a chlorine atom or a bromine atom is preferable, and a chlorine atom is more preferable.
- Examples of the alkoxy groups represented by X 1 and X 2 include methoxy group, ethoxy group, propyloxy group, i-propyloxy group, butyloxy group, i-butyloxy group, s-butyloxy group, t-butyloxy group and pentyloxy group.
- AZn-2 Specific examples of the compound represented by the formula (AZn-2) include compounds having the following structures.
- the nitrogen atom is coordinated to the zinc (Zn) atom, but the nitrogen atom may not be coordinated to the zinc atom.
- azo metal complex C.I. I. Pigment Yellow 150 and the like.
- a nickel azobarbiturate complex having the following structure can also be used.
- azo metal complex at least one anion selected from an azo compound represented by the following formula (Az1) and an azo compound having a telecommunication structure thereof, two or more kinds of metal ions, and a melamine compound are used.
- Azo metal complex Az containing the azo metal complex Az can also be used.
- R 1 and R 2 are independently -OH or -NR 5 R 6
- R 5 to R 7 are respectively.
- the number of carbon atoms of the alkyl group represented by R 5 to R 7 is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear.
- the alkyl group may have a substituent.
- the substituent is preferably a halogen atom, a hydroxy group, an alkoxy group, a cyano group and an amino group.
- the azo metal complex Az comprises at least one anion selected from the azo compound represented by the above formula (Az1) and an azo compound having a tautomeric structure thereof, a metal ion containing at least Zn 2+ and Cu 2+, and melamine. It is preferably a pigment containing a compound.
- No. 0011 to 0062, 0139 to 0190, paragraphs 0010 to 0065, 0142 to 0222 of JP-A-2017-171915 can be referred to, and the contents thereof are incorporated in the present specification.
- the phthalocyanine metal complex examples include a phthalocyanine metal complex (metal phthalocyanine pigment) having copper, zinc, aluminum, iron, cobalt, vanadium, titanium or magnesium as a central metal.
- a phthalocyanine metal complex metal phthalocyanine pigment
- Specific examples of the phthalocyanine metal complex include green pigments such as Color Index (CI) Pigment Green 7, 36, 58, 59, 62, 63, and C.I. I. Examples thereof include blue pigments such as Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6.
- Color pigment examples of the chromatic pigment include pigments having a maximum absorption wavelength in the wavelength range of 400 to 700 nm. For example, yellow pigments, orange pigments, red pigments, green pigments, purple pigments, blue pigments and the like can be mentioned.
- the pigment used in the coloring composition of the present invention preferably contains at least one selected from a yellow pigment, a green pigment and a red pigment, and more preferably contains a yellow pigment.
- yellow pigment examples include an azomethine compound, an azo compound, an isoindrin compound, a pteridine compound, and a quinophthalone compound, preferably an azomethine compound and an azo compound, and more preferably an azomethine metal complex and an azo metal complex.
- the azomethine metal complex is preferable because it can form pixels having better resistance to the developing solution. Examples of the azomethine metal complex and the azometal complex include those described above.
- azomethine metal complex and the yellow pigment other than the azometal complex include C.I. I. Pigment Yellow 1,2,3,4,5,6,10,11,12,13,14,15,16,17,18,20,24,31,32,34,35,35: 1,36, 36: 1,37,37: 1,40,42,43,53,55,60,61,62,63,65,73,74,77,81,83,86,93,94,95,97, 98,100,101,104,106,108,109,110,113,114,115,116,118,119,120,123,125,126,127,128,137,138,139,147,148, 151,152,153,154,155,156,161,162,164,166,167,168,169,170,171,172,173,174,175,176,177,179,180,181,1822 185,187,188,193,194,199,213,214,215,228,231,232 (methine type
- yellow pigment examples include the quinophthalone compounds described in paragraphs 0011 to 0034 of JP2013-054339, the quinophthalone compounds described in paragraphs 0013 to 0058 of JP-A-2014-026228, and JP-A-2018-0626444.
- quinophthalone compounds described in JP2012-226110A Compounds, quinophthalone compounds described in JP-A-2008-074987, quinophthalone compounds described in JP-A-2008-081565, and quinophthalone compounds described in JP-A-2008-074986.
- the quinophthalone compound described in JP-A-2019-008014, and the quinophthalone compound described in Patent No. 6607427 can also be used. Further, a multimerized version of these compounds is also preferably used from the viewpoint of improving the color value.
- C.I. I. Pigment Yellow 117, 129, 138, 139, 150, 185 are preferred, and C.I. I. Pigment Yellow 117,129 is more preferred, and C.I. I. Pigment Yellow 129 is even more preferred.
- red pigment examples include diketopyrrolopyrrole compounds, anthraquinone compounds, azo compounds, naphthol compounds, azomethine compounds, xanthene compounds, quinacridone compounds, perylene compounds and thioindigo compounds, which can form pixels having more excellent developer resistance. For this reason, a diketopyrrolopyrrole compound and a quinacridone compound are preferable, and a diketopyrrolopyrrole compound is more preferable.
- red pigments include C.I. I. Pigment Red 1,2,3,4,5,6,7,9,10,14,17,22,23,31,38,41,48:1,48: 2,48:3,48:4 49,49: 1,49: 2,52: 1,52: 2,53: 1,57: 1,60: 1,63: 1,66,67,81: 1,81: 2,81: 3, 83,88,90,105,112,119,122,123,144,146,149,150,155,166,168,169,170,171,172,175,176,177,178,179,184 185,187,188,190,200,202,206,207,208,209,210,216,220,224,226,242,246,254,255,264,269,270,272,279,291 294, 295, 296, 297 and the like can be mentioned.
- red pigment a diketopyrrolopyrrole compound in which at least one bromine atom is substituted in the structure described in JP-A-2017-201384, diketopyrrolopyrrole described in paragraphs 0016 to 0022 of Patent No. 6248838.
- the red pigment described in Japanese Patent No. 6516119, the red pigment described in Japanese Patent No. 6525101, and the like can also be used.
- red pigment a compound having a structure in which an aromatic ring group in which a group in which an oxygen atom, a sulfur atom or a nitrogen atom is bonded to an aromatic ring is bonded to a diketopyrrolopyrrole skeleton can also be used. ..
- C.I. I. Pigment Red 122,177,254,255,264,269,272 is preferred.
- I. Pigment Red 254,255,264,272 is more preferred.
- green pigment examples include phthalocyanine compounds and squarylium compounds, and phthalocyanine compounds are preferable, and phthalocyanine metal complexes are more preferable, because pixels having better developer resistance can be formed.
- the green pigment examples include C.I. I. Pigment Green 7, 10, 36, 37, 58, 59, 62, 63, 64, 65, 66 and the like. Further, as a green pigment, a halogenated zinc phthalocyanine pigment having an average of 10 to 14 halogen atoms in one molecule, an average of 8 to 12 bromine atoms, and an average of 2 to 5 chlorine atoms. Can also be used. Specific examples include the compounds described in International Publication No. 2015/118720. Further, as a green pigment, a compound described in Chinese Patent Application No. 106900927, a phthalocyanine compound having a phosphate ester as a ligand according to International Publication No.
- Phthalocyanine compounds, phthalocyanine compounds described in JP-A-2018-180023, compounds described in JP-A-2019-038958, squarylium compounds described in paragraph numbers 0141 to 0151 of International Publication No. 2019/167589, etc. Can be used.
- examples of the green pigment include C.I. I. Pigment greens 7, 36, 58, 59, 62, 63 are preferred.
- C.I. I. Pigment Violet 1 19, 23, 27, 32, 37, 42, 60, 61 and the like.
- the coloring composition may contain two or more kinds of chromatic pigments.
- a coloring composition containing a yellow pigment and a green pigment can be preferably used as a coloring composition for forming green pixels of a color filter.
- the yellow pigment in this case preferably contains an azomethine metal complex.
- the green pigment preferably contains a phthalocyanine metal complex.
- a coloring composition containing a yellow pigment and a red pigment can be preferably used as a coloring composition for forming red pixels of a color filter.
- the yellow pigment in this case preferably contains an azomethine metal complex.
- the red pigment preferably contains a diketopyrrolopyrrole compound.
- the coloring composition may contain two or more kinds of chromatic pigments, and a combination of two or more kinds of chromatic pigments may form black.
- a coloring composition is preferably used as a coloring composition for forming an infrared transmission filter.
- the following are examples of combinations of chromatic pigments when black is formed by a combination of two or more chromatic pigments.
- A1 An embodiment containing a red pigment, a blue pigment, and a yellow pigment.
- A2 An embodiment containing a red pigment, a blue pigment, a yellow pigment, and a purple pigment.
- A3 An embodiment containing a red pigment, a blue pigment, a yellow pigment, a purple pigment, and a green pigment.
- A5 An embodiment containing a yellow pigment and a purple pigment.
- the black pigment is not particularly limited, and known ones can be used.
- inorganic pigments such as carbon black, titanium black, and graphite are mentioned, and carbon black and titanium black are preferable, and titanium black is more preferable.
- Titanium black is black particles containing a titanium atom, and low-order titanium oxide or titanium oxynitride is preferable. Titanium black can modify the surface as needed for the purpose of improving dispersibility and suppressing cohesion.
- Titanium black preferably has a small primary particle size and an average primary particle size of each particle. Specifically, it is preferable that the average primary particle size is 10 to 45 nm. Titanium black can also be used as a dispersion. For example, a dispersion containing titanium black particles and silica particles and having a content ratio of Si atoms and Ti atoms in the dispersion adjusted to be in the range of 0.20 to 0.50 can be mentioned. Regarding the above dispersion, the description in paragraphs 0020 to 0105 of JP2012-169556A can be referred to, and the contents thereof are incorporated in the present specification.
- titanium black products examples include titanium black 10S, 12S, 13R, 13M, 13M-C, 13RN, 13M-T (trade name: manufactured by Mitsubishi Materials Corporation), Tilac D (Tilack) D (trade name: manufactured by Mitsubishi Materials Corporation). Product name: Ako Kasei Co., Ltd.) and the like.
- the content of the pigment in the total solid content of the coloring composition is preferably 20% by mass or more, more preferably 30% by mass or more, further preferably 40% by mass or more, and 50% by mass. It is particularly preferable to exceed 55% by mass, and most preferably 55% by mass or more.
- the upper limit is preferably 80% by mass or less, more preferably 75% by mass or less, and further preferably 70% by mass or less.
- the content of the pigment having a metal atom in the pigment contained in the coloring composition is preferably 15% by mass or more, more preferably 15.5% by mass or more, and preferably 16% by mass or more. More preferred.
- the upper limit can be 100% by mass, 95% by mass or less, or 90% by mass or less.
- the content of the azomethine metal complex in the pigment contained in the coloring composition is preferably 15% by mass or more, more preferably 15.5% by mass or more, still more preferably 16% by mass or more. ..
- the upper limit can be 100% by mass, 95% by mass or less, or 90% by mass or less.
- the content of the yellow pigment in the pigment contained in the coloring composition is preferably 30% by mass or more, more preferably 33% by mass or more, and further preferably 35% by mass or more.
- the upper limit can be 100% by mass, 95% by mass or less, or 90% by mass or less.
- the content of the yellow pigment in the pigment is preferably 90% by mass or more, more preferably 95% by mass or more. It is preferably 99% by mass or more, and more preferably 99% by mass or more.
- the coloring composition of the present invention is used as a coloring composition for forming green pixels of a color filter, it is preferable to use a pigment containing a yellow pigment and a green pigment.
- the content of the azomethine metal complex is preferably 3 parts by mass or more, more preferably 5 parts by mass or more, and further preferably 10 parts by mass or more with respect to 100 parts by mass of the green pigment. ..
- the coloring composition of the present invention is used as a coloring composition for forming red pixels of a color filter, it is preferable to use a pigment containing a yellow pigment and a red pigment.
- the content of the azomethine metal complex is preferably 3 parts by mass or more, more preferably 5 parts by mass or more, and further preferably 10 parts by mass or more with respect to 100 parts by mass of the red pigment. ..
- the coloring composition of the present invention can contain a dye.
- the dye is not particularly limited, and known dyes can be used. Examples of the dye include chromatic dyes and black dyes.
- the chromatic dyes include pyrazole azo compound, anilino azo compound, triarylmethane compound, anthraquinone compound, anthrapyridone compound, benzylidene compound, oxonol compound, pyrazolotriazole azo compound, pyridone azo compound, cyanine compound, phenothiazine compound and pyrrolopyrazole azomethine compound.
- Xanthene compound phthalocyanine compound
- benzopyran compound indigo compound
- pyrromethene compound pyrromethene compound
- black dye examples include a bisbenzofuranone compound, an azomethine compound, a perylene compound, and an azo compound.
- the content of the dye is preferably 100 parts by mass or less, more preferably 50 parts by mass or less, further preferably 30 parts by mass or less, and 10 parts by mass or less with respect to 100 parts by mass of the pigment. Is particularly preferable.
- the coloring composition of the present invention may be substantially free of dyes. When the coloring composition of the present invention contains substantially no dye, the content of the dye in the total solid content of the coloring composition of the present invention is preferably 0.1% by mass or less, preferably 0.05% by mass. The following is more preferable, and it is particularly preferable that the content is not contained.
- the coloring composition of the present invention is at least one compound selected from the compound S-1 represented by the formula (1) and the compound S-2 in which the above-mentioned compound S-1 is coordinated to a metal atom.
- R 1 represents a hydrogen atom, an alkyl group or an aryl group
- R 2 to R 9 independently represent a hydrogen atom or a substituent
- two adjacent groups of R 2 to R 9 are adjacent to each other. May combine to form a ring; however, any one of R 2 to R 9 contains a group represented by the formula (R-1); -W 1- (X 1 ) n ...
- W 1 represents a single bond or an n + 1 valent linking group
- X 1 represents an acid group or a basic group
- n represents an integer of 1-5; where W 1 is simply. In the case of binding, n is 1.
- the number of carbon atoms of the alkyl group represented by R 1 in the formula (1) is preferably 1 to 30, more preferably 1 to 15, and even more preferably 1 to 8.
- the alkyl group may be linear, branched or cyclic, but is preferably linear or branched, more preferably linear.
- the alkyl group may have a substituent. Examples of the substituent include the substituent T described later.
- the aryl group represented by R 1 in the formula (1) preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and even more preferably 6 to 12 carbon atoms.
- the aryl group may have a substituent. Examples of the substituent include the substituent T described later.
- R 1 of the formula (1) is preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.
- R 2 to R 9 independently represent a hydrogen atom or a substituent.
- the substituent include a substituent T described later and a group represented by the formula (R-1).
- the substituent other than the group represented by the formula (R-1) include a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, a cyano group, a hydroxy group, a nitro group, an alkoxy group and an aryl.
- Halogen atom, aryl group, cyano group or nitro group is particularly preferable.
- R 3 , R 7 or R 8 contains a group represented by the formula (R-1), and R 7 or R 8 contains a group represented by the formula (R-1). It is more preferable to include, and it is further preferable that R 7 or R 8 is a group represented by the formula (R-1). Further, R 8 is a group represented by the formula (R-1), and R 6 , R 7 and R 9 are hydrogen atoms, respectively, or R 7 is a group represented by the formula (R-1). It is preferable that R 6 , R 8 and R 9 are hydrogen atoms, respectively.
- Two neighboring groups of R 2 ⁇ R 9 may form a ring.
- the ring formed is preferably an aromatic ring.
- R 2 and R 3 are bonded to form an aromatic ring (preferably a benzene ring).
- W 1 represents a single bond or an n + 1 valent linking group.
- the n + 1 valent linking group represented by W 1 includes an aliphatic hydrocarbon group, an aromatic hydrocarbon group, a heterocyclic group, -O-, -S-, -CO-, -COO-, -OCO-, and -SO. 2 -, - NR W -, - NR W CO -, - CONR W -, - NR W SO 2 -, - SO 2 NR W - and include a group formed by combination of these groups, R W is a hydrogen atom, an alkyl Represents a group or aryl group.
- the number of carbon atoms of the aliphatic hydrocarbon group is preferably 1 to 20, more preferably 2 to 20, further preferably 2 to 10, and particularly preferably 2 to 5.
- the aliphatic hydrocarbon group may be linear, branched or cyclic. Further, the cyclic aliphatic hydrocarbon group may be either monocyclic or polycyclic.
- the number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 18, more preferably 6 to 14, and even more preferably 6 to 10.
- the aromatic hydrocarbon group is preferably a monocyclic or an aromatic hydrocarbon group having a condensed ring having 2 to 4 condensation numbers.
- the aromatic hydrocarbon group is preferably a benzene ring group.
- the heterocyclic group is preferably a single ring or a fused ring having 2 to 4 condensation numbers.
- the number of heteroatoms constituting the ring of the heterocyclic group is preferably 1 to 3.
- the hetero atom constituting the ring of the heterocyclic group is preferably a nitrogen atom, an oxygen atom or a sulfur atom.
- the number of carbon atoms constituting the ring of the heterocyclic group is preferably 3 to 30, more preferably 3 to 18, and even more preferably 3 to 12.
- the heterocyclic group is preferably a triazine ring group.
- Aliphatic hydrocarbon groups, aromatic hydrocarbon groups and heterocyclic groups may have substituents. Examples of the substituent include the groups listed in Substituent T described later.
- the number of carbon atoms of the alkyl group represented by R W is preferably 1-20, more preferably 1-15, 1-8 is more preferable.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched, and more preferably linear.
- Alkyl group R W represents may further have a substituent. Examples of the substituent include the substituent T described later.
- the number of carbon atoms of the aryl group R W represents is preferably 6 to 30, more preferably 6 to 20, more preferably 6 to 12.
- Aryl groups R W represents may further have a substituent. Examples of the substituent include the substituent T described later.
- X 1 represents an acid group or a basic group, and is preferably an acid group. Further, when X 1 of the formula (R-1) is a basic group, W 1 is preferably an n + 1 valent linking group.
- Examples of the acid group represented by X 1 include a carboxy group, a sulfo group, a phosphoric acid group, a group represented by -SO 2 NHSO 2 Rf 1 , or a salt thereof.
- Rf 1 in the group represented by -SO 2 NHSO 2 Rf 1 represents a group containing a fluorine atom.
- Examples of the group containing a fluorine atom represented by Rf 1 include a fluorine atom, an alkyl group containing a fluorine atom, and an aryl group containing a fluorine atom, and an alkyl group containing a fluorine atom is preferable.
- the number of carbon atoms of the alkyl group containing a fluorine atom is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3.
- the aryl group containing a fluorine atom preferably has 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms, and even more preferably 6.
- Examples of the atoms or atomic groups constituting the salt include alkali metal ions (Li + , Na + , K +, etc.), alkaline earth metal ions (Ca 2+ , Mg 2+, etc.), ammonium cations, and nitrogen-containing heterocycles. Ammonium ion containing is preferable, and pyridinium ion is more preferable.
- the acid group represented by X 1 is preferably a sulfo group, a phosphoric acid group, a group represented by -SO 2 NHSO 2 Rf 1 , or a salt thereof, and a sulfo group, -SO 2 NHSO 2 Rf 1 . or a group represented by,, more preferably a salt thereof, sulfo group salt, a group represented by -SO 2 NHSO 2 Rf 1 or a group represented by -SO 2 NHSO 2 Rf 1 It is more preferably a salt.
- Examples of the basic group represented by X 1 include an amino group, a salt of an ammonium group, and a phthalimidemethyl group, preferably a salt of an amino group and an ammonium group, and more preferably an amino group.
- Examples of the atom or atomic group constituting the salt in the salt of the ammonium group include hydroxide ion, halogen ion, carboxylic acid ion, sulfonic acid ion, phenoxide ion and the like.
- Examples of the amino group include a group represented by ⁇ NRx 1 Rx 2 and a cyclic amino group.
- Rx 1 and Rx 2 independently represent a hydrogen atom, an alkyl group and an aryl group, and are preferably alkyl groups.
- the number of carbon atoms of the alkyl group is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3.
- the alkyl group may be linear, branched or cyclic, but linear or branched is preferable, and linear is more preferable.
- the alkyl group may have a substituent. Examples of the substituent include the substituent T described later.
- the aryl group preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and even more preferably 6 to 12 carbon atoms.
- the aryl group may have a substituent. Examples of the substituent include the substituent T described later.
- Examples of the cyclic amino group include a pyrrolidine group, a piperidine group, a piperazine group, a morpholine group and the like. These groups may further have a substituent. Examples of the substituent include the substituent T described later. Specific examples of the substituent include an alkyl group and an aryl group.
- n is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.
- One preferred embodiment of the group represented by the formula (R-1) is an embodiment in which W 1 is a single bond, X 1 is an acid group, and n is 1. Further, as one of the other preferable embodiments of the group represented by the formula (R-1), an embodiment which is a group represented by the following formula (R-11) can be mentioned. -W 11 -W 12 - (W 13 -X 1) n ⁇ (R-11)
- W 11 of the formula (R-11) is a single bond, -O-, -S-, -CO-, -COO-, -OCO-, -OCO 2- , -NR W- , -SO 2 -,- NR W CO -, - CONR W -, - NR W CO 2 -, - OCONR W -, - NR W SO 2 - or -SO 2 NR W - Arawashi a, R W is a hydrogen atom, an alkyl group or an aryl group show. Number of carbon atoms of the alkyl group R W represents preferably 1 to 20, more preferably from 1 to 15, 1 to 8 are more preferred.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched, and more preferably linear.
- Alkyl group R W represents may further have a substituent. Examples of the substituent include the substituent T described later.
- the number of carbon atoms of the aryl group R W represents is preferably 6 to 30, more preferably 6 to 20, more preferably 6 to 12.
- Aryl groups R W represents may further have a substituent. Examples of the substituent include the substituent T described later.
- R W may form a ring with X 1. For example, if a group X 1 is represented by -NRx 1 Rx 2, R W may form a ring with Rx 1 or Rx 2.
- the ring formed is preferably a 5-membered ring or a 6-membered ring.
- W 12 of the formula (R-11) represents a single bond or a (n + 1) -valent linking group. However, when n is 1, W 12 is a single bond or a divalent linking group, and when n is 2 or more, W 12 is an n + 1 valent linking group.
- W 12 an aliphatic hydrocarbon group, an aromatic hydrocarbon group, a heterocyclic group, -O-, -S-, -CO-, -COO-, -OCO-, -SO 2- , -NR W -, - N ⁇ , - NR W CO -, - CONR W -, - NR W SO 2 -, - SO 2 NR W - and include groups in which a combination of these.
- R W are as defined above R w.
- W 12 is preferably a group containing at least one selected from an aliphatic hydrocarbon group, an aromatic hydrocarbon group and a heterocyclic group.
- Examples of the aliphatic hydrocarbon group, the aromatic hydrocarbon group and the heterocyclic group include those described above.
- Specific examples of the linking group represented by W 12 include at least one selected from an aliphatic hydrocarbon group; an aromatic hydrocarbon group; a heterocyclic group; an aliphatic hydrocarbon group, an aromatic hydrocarbon group and a heterocyclic group. , -O-, -S-, -CO-, -COO-, -OCO-, -SO 2- , -NR W- , -N ⁇ , -NR W CO-, -CONR W- , -NR W SO 2 - and -SO 2 NR W - such as a group formed by combining at least one selected from the like.
- a preferred embodiment of W 12 is a group containing at least one selected from an aromatic hydrocarbon group and a heterocyclic group.
- Examples of the group containing at least one selected from the aromatic hydrocarbon group and the heterocyclic group include groups represented by the following formulas (W12-1) to (W12-6).
- a 1 in the formula (W12-1) represents O or NR W12.
- R W12 has the same meaning as defined above R w.
- n 1 represents an integer of 1 to 4.
- a 2 and n 2 in the formula (W12-2) are synonymous with A 1 and n 1.
- B 2 is a single bond, -O-, -S-, -CO-, -COO-, -OCO-, -SO 2- , -NR W- , -NR W CO-, -CONR W- , -NR W Represents SO 2- or -SO 2 NR W-.
- R W12 has the same meaning as defined above R w.
- T 3 in the formula (W12-3) represents the substituent T described later.
- a 3 is synonymous with A 1.
- T 4 , A 4 , and B 4 in the formula (W12-4) are synonymous with T 3 , A 1 , and B 2.
- a 5 in the formula (W12-5) is synonymous with A 1.
- a 6 and B 6 in the formula (W12-6) are synonymous with A 1 and B 2.
- the T 3 and T 4 are preferably a hydroxy group, an amino group, an alkoxy group, an aryloxy group, a thioalkyl group, a thioaryl group or a halogen atom, and more preferably a hydroxy group or an amino group.
- the amino group is preferably an alkylamino group or an arylamino group, more preferably an arylamino group.
- W 13 of the formula (R-11) represents an alkylene group.
- the alkylene group preferably has 2 to 10 carbon atoms, more preferably 2 to 8 carbon atoms, and even more preferably 2 to 5 carbon atoms.
- X 1 in the formula (R-11) represents an acid group or a basic group.
- X 1 of formula (R-11) has the same meaning as X 1 in formula (R-1).
- N in the formula (R-11) represents an integer of 1 to 5, preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.
- substituent T examples include the following groups.
- Halogen atom eg, fluorine atom, chlorine atom, bromine atom, iodine atom
- alkyl group preferably an alkyl group having 1 to 30 carbon atoms
- alkenyl group preferably an alkenyl group having 2 to 30 carbon atoms
- alkynyl group Preferably an alkynyl group having 2 to 30 carbon atoms
- an aryl group preferably an aryl group having 6 to 30 carbon atoms
- a heteroaryl group preferably a heteroaryl group having 1 to 30 carbon atoms
- an alkoxy group preferably an alkoxy group having 1 to 30 carbon atoms.
- an acyl group having 2 to 30 carbon atoms an alkoxycarbonyl group (preferably an alkoxycarbonyl group having 2 to 30 carbon atoms), an aryloxycarbonyl group (preferably an aryloxycarbonyl group having 7 to 30 carbon atoms), and a heteroaryloxy.
- a carbonyl group (preferably a heteroaryloxycarbonyl group having 2 to 30 carbon atoms), an acyloxy group (preferably an acyloxy group having 2 to 30 carbon atoms), an acylamino group (preferably an acylamino group having 2 to 30 carbon atoms), an aminocarbonyl Amino group (preferably aminocarbonylamino group having 2 to 30 carbon atoms), alkoxycarbonylamino group (preferably alkoxycarbonylamino group having 2 to 30 carbon atoms), aryloxycarbonylamino group (preferably 7 to 30 carbon atoms) Aryloxycarbonylamino group), sulfamoyl group (preferably sulfamoyl group having 0 to 30 carbon atoms), sulfamoylamino group (preferably sulfamoylamino group having 0 to 30 carbon atoms), carbamoyl group (preferably having 0 to 30 carbon atoms).
- alkylthio groups preferably alkylthio groups having 1 to 30 carbon atoms
- arylthio groups preferably arylthio groups having 6 to 30 carbon atoms
- heteroarylthio groups preferably 1 to 30 carbon atoms.
- alkylsulfonyl group preferably an alkylsulfonyl group having 1 to 30 carbon atoms
- alkylsulfonylamino group preferably an alkylsulfonylamino group having 1 to 30 carbon atoms
- arylsulfonyl group preferably carbon
- arylsulfinyl groups 6 to 30 arylsulfinyl groups), heteroarylsulfinyl groups (preferably heteroarylsulfinyl groups with 1 to 30 carbon atoms), ureido groups (preferably ureido groups with 1 to 30 carbon atoms), hydroxy groups, nitro groups, imides.
- substituent include the group described in the above-mentioned Substituent T.
- Compound S-1 is preferably a compound represented by the formula (11).
- R 21 represents a hydrogen atom, an alkyl group or an aryl group
- R 22 to R 31 each independently represent a hydrogen atom or a substituent; however, any one of R 22 to R 31 is used. It is a group represented by the formula (R-1).
- R 21 of the formula (11) has the same meaning as R 1 of the formula (1), and the preferable range is also the same.
- substituent represented by R 22 to R 31 of the formula (11) include a substituent T and a group represented by the formula (R-1).
- substituent other than the group represented by the formula (R-1) include a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, a cyano group, a hydroxy group, a nitro group, an alkoxy group and an aryl.
- Halogen atom, aryl group, cyano group or nitro group is particularly preferable.
- R 24 , R 29 or R 30 is preferably a group represented by the formula (R-1), and R 29 or R 30 is a group represented by the formula (R-1). It is more preferable that R 30 is a group represented by the formula (R-1). Moreover, it is preferable that the remaining group is a hydrogen atom.
- compound S-2 is a compound having a structure in which the above-mentioned compound S-1 is coordinated to a metal atom.
- the metal atom include copper, zinc, iron, titanium, aluminum, tin, magnesium and chromium, with copper and zinc being preferred.
- one compound S-1 may be coordinated to these metal atoms, or two or more compounds may be coordinated.
- a ligand other than the compound S-1 may be further coordinated to the metal atom.
- the ligands include heterocyclic compounds (eg, pyridine, pyrimidine, imidazole, pyrazole, triazole, tetrazole, quinoline, 1,10-phenanthroline, etc.), protonic compounds (eg, water, methanol, ethanol, etc.), amine compounds (eg, water, methanol, ethanol, etc.).
- heterocyclic compounds eg, pyridine, pyrimidine, imidazole, pyrazole, triazole, tetrazole, quinoline, 1,10-phenanthroline, etc.
- protonic compounds eg, water, methanol, ethanol, etc.
- amine compounds eg, water, methanol, ethanol, etc.
- a dinuclear complex may be used for compound S-2.
- the compound S-2 is preferably a compound represented by the formula (1a), and more preferably a compound represented by the formula (11a).
- the nitrogen atom is coordinated to the metal atom (M 1 or M 2 ), but depending on the state of the metal atom, the nitrogen atom is coordinated to the metal atom (M 1 or M 2). It may not be.
- R 1 represents a hydrogen atom, an alkyl group or an aryl group
- R 2 to R 9 independently represent a hydrogen atom or a substituent
- two adjacent groups of R 2 to R 9 are adjacent to each other. May be bonded to form a ring, where M 1 represents a metal atom to which the ligand may be coordinated; however, any one of R 2 to R 9 may be of the formula (R-1). ) Is included.
- R 21 represents a hydrogen atom, an alkyl group or an aryl group
- R 22 to R 31 independently represent a hydrogen atom or a substituent
- M 2 is coordinated with a ligand.
- R 1 ⁇ R 9 of formula (1a) has the same meaning as R 1 ⁇ R 9 of formula (1), and preferred ranges are also the same.
- R 21 ⁇ R 31 of formula (11a) has the same meaning as R 21 ⁇ R 31 of formula (11), and preferred ranges are also the same.
- the M 1 and good metal atom ligand is be coordinated to M 2 represents the formula (11a) of the formula (1a), copper, zinc, iron, titanium, aluminum, tin, magnesium and chromium mentioned Copper and zinc are preferred.
- Examples of the ligand that may be coordinated to these metal atoms include the ligands mentioned in the ligands other than the compound S-1. Further, the compound represented by the formula (1) may be further coordinated.
- the compound S is preferably a compound represented by the formula (1-1), the formula (1a-1), the formula (11-1) or the formula (11a-1). These compounds are also the compounds of the present invention.
- the nitrogen atom is coordinated to the metal atom (M 1a or M 2a ), but the nitrogen atom is coordinated to the metal atom (M 1a or M 2a ) depending on the state of the metal atom. It may not be.
- R 1a represents a hydrogen atom, an alkyl group or an aryl group.
- R 2a ⁇ R 9a are each independently hydrogen atom, a salt of a carboxyl group, a salt of sulfo group, salts of the phosphate group, the group represented by -SO 2 NHSO 2 Rf 1, in -SO 2 NHSO 2 Rf 1 Salts of groups represented, halogen atoms, alkyl groups, alkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, cyano groups, hydroxy groups, nitro groups, alkoxy groups, aryloxy groups, silyloxy groups, heterocyclic oxy groups, Acyloxy group, carbamoyloxy group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, alkylsulfonylamino
- M 1a represents a metal atom to which the ligand may be coordinated; However, any one of R 2a ⁇ R 9a, salts of sulfo group, a group represented by -SO 2 NHSO 2 Rf 1, or a salt of the group represented by -SO 2 NHSO 2 Rf 1.
- R 21a represents a hydrogen atom, an alkyl group or an aryl group.
- R 22a ⁇ R 31a are each independently hydrogen atom, a salt of a carboxyl group, a salt of sulfo group, salts of the phosphate group, the group represented by -SO 2 NHSO 2 Rf 1, in -SO 2 NHSO 2 Rf 1 Salts of groups represented, halogen atoms, alkyl groups, alkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, cyano groups, hydroxy groups, nitro groups, alkoxy groups, aryloxy groups, silyloxy groups, heterocyclic oxy groups, Acyloxy group, carbamoyloxy group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, alkylsulfonyla
- M 2a represents a metal atom to which the ligand may be coordinated; However, any one of R 22a ⁇ R 31a, salts of sulfo group, a group represented by -SO 2 NHSO 2 Rf 1, or a salt of the group represented by -SO 2 NHSO 2 Rf 1.
- R 3a , R 7a or R 8a is a salt of a sulfo group, a group represented by -SO 2 NHSO 2 Rf 1 , or -SO 2 NHSO 2.
- R 7a or R 8a are, salts of sulfo group, a group represented by -SO 2 NHSO 2 Rf 1, or, in -SO 2 NHSO 2 Rf 1 more preferably salts of radicals represented
- R 8a are, sulfo group salt, a group represented by -SO 2 NHSO 2 Rf 1 or a group represented by -SO 2 NHSO 2 Rf 1 It is more preferably salt.
- R 24a , R 29a or R 30a is a salt of a sulfo group, a group represented by -SO 2 NHSO 2 Rf 1 , or -SO 2 NHSO 2.
- R 29a or R 30a is, salts sulfo group, a group represented by -SO 2 NHSO 2 Rf 1, or, in -SO 2 NHSO 2 Rf 1 more preferably salts of radicals represented
- R 30a is, sulfo group salt, a group represented by -SO 2 NHSO 2 Rf 1 or a group represented by -SO 2 NHSO 2 Rf 1 It is more preferably salt.
- the M 1a and Formula (11a-1) optionally a metal atom with which ligand is coordinated represented by M 2a of the formula (1a-1), copper, zinc, iron, titanium, aluminum, tin, magnesium And chromium, with copper and zinc being preferred.
- the ligand that may be coordinated to these metal atoms include the ligands mentioned in the ligands other than the compound S-1. Further, the compound represented by the formula (1-1) or the compound represented by (11-1) may be further coordinated.
- compound S examples include compounds (S-1) to (S-20) described in Examples described later.
- Examples of the method for synthesizing the compound S include the methods shown below.
- the reaction can be carried out by simultaneously mixing a hydroxy-substituted arylaldehyde or a hydroxy-substituted aniline with a metal source, or the hydroxy-substituted arylaldehyde and the hydroxy-substituted aniline are first reacted and then reacted. It can also be reacted with a metal source.
- a metal source for example, an acidic compound (for example, acetic acid, sulfuric acid, etc.) and a basic compound (for example, triethylamine, pyridine, etc.) may be added.
- a known solvent can be selected, and an alcohol solvent (for example, methanol, ethanol, isopropanol, propylene glycol monomethyl ether, etc.) and an amide solvent (for example, N, N-dimethylacetamide, N, N-dimethylformamide, N-) can be selected.
- an alcohol solvent for example, methanol, ethanol, isopropanol, propylene glycol monomethyl ether, etc.
- an amide solvent for example, N, N-dimethylacetamide, N, N-dimethylformamide, N-
- Any metal source used for synthesizing Pigment Yellow 129 type compound can be used without particular limitation, and examples thereof include acetates, halide salts, and sulfonates. Further, a ligand such as 8-hydroxyquinoline may be mixed and reacted.
- Hydroxy-substituted arylaldehydes and hydroxy-substituted anilines having an acid group or a base in the synthesis method of (i) are described in, for example, Japanese Patent Publication No. 2013-510156 and Chemistry-A European Journal, 2009, vol. 15, sha-pu 33, p. It can be synthesized with reference to 8283-8295, etc.
- the content of compound S in the total solid content of the coloring composition is preferably 0.1 to 30% by mass.
- the lower limit is preferably 0.5% by mass or more, and more preferably 1% by mass or more.
- the upper limit is preferably 20% by mass or less, and more preferably 15% by mass or less.
- the content of the compound S is preferably 1 to 50 parts by mass with respect to 100 parts by mass of the pigment.
- the lower limit is preferably 3 parts by mass or more, more preferably 5 parts by mass or more, and further preferably 10 parts by mass or more.
- the upper limit is preferably 40 parts by mass or less, and more preferably 30 parts by mass or less.
- the compound S may be only one kind or may contain two or more kinds. When two or more kinds are contained, the total amount thereof is preferably in the above range. Further, the compound S may contain a structural isomer, but the ratio of the structural isomer in the compound S is preferably 50% by mass or less, more preferably 30% by mass or less, and 10% by mass. % Or less, and particularly preferably free of structural isomers.
- the coloring composition of the present invention contains a resin P (hereinafter, also referred to as a resin).
- the resin is blended, for example, for the purpose of dispersing a pigment or the like in a coloring composition or for the purpose of a binder.
- a resin mainly used for dispersing a pigment or the like in a coloring composition is also referred to as a dispersant.
- such an application of the resin is an example, and the resin can be used for purposes other than such an application.
- the resin contained in the coloring composition of the present invention is a graft resin P-1 having a graft chain containing at least one structure selected from a polyester structure, a polyether structure and a poly (meth) acrylic structure (hereinafter, graft resin P).
- graft resin P a graft chain containing at least one structure selected from a polyester structure, a polyether structure and a poly (meth) acrylic structure
- Block copolymer P-2 containing at least one structure selected from polyester structure, polyether structure and poly (meth) acrylic structure
- resin P-3 hereinafter, resin P-3 in which at least one end of a polymer chain containing at least one structure selected from a polyester structure, a polyether structure and a poly (meth) acrylic structure is sealed with an acid group. Includes at least one selected from 3).
- the graft resin P-1, the block copolymer P-2, and the resin P-3 are collectively referred to as a specific resin.
- the graft resin P-1 When the graft resin P-1 is used as the specific resin, the strength of the film obtained by using the coloring composition becomes stronger due to the network structure, and pixels having excellent scratch resistance can be formed. Further, when the block copolymer P-2 is used as the specific resin, the coatability of the colored composition can be improved. Further, when the resin P-3 is used as the specific resin, the resin P-3 has a relatively high adsorption rate to the pigment, so that the pigment is dispersed in the composition in a shorter time during the production of the coloring composition. Can be made to.
- Only one type of specific resin may be used, or two or more types may be used in combination.
- two types of specific resins are used in combination, two or more types of graft resin P-1 may be used in combination, two or more types of block copolymer P-2 may be used in combination, and two types of resin P-3 may be used in combination.
- the above may be used in combination, or one or more of the graft resin P-1 and one or more of the block copolymer P-2 may be used in combination, and one or more of the graft resin P-1 and the resin P-3 may be used in combination.
- one or more of the graft resin P-1, one or more of the block copolymer P-2, and one or more of the resin P-3 may be used in combination.
- the graft resin P-1 has a graft chain containing at least one structure selected from a polyester structure, a polyether structure and a poly (meth) acrylic structure.
- Examples of the polyester structure include structures represented by the following formula (G-1), formula (G-4) or formula (G-5).
- Examples of the polyether structure include a structure represented by the following formula (G-2).
- Examples of the poly (meth) acrylic structure include a structure represented by the following formula (G-3).
- RG1 and RG2 each represent an alkylene group.
- RG3 represents a hydrogen atom or a methyl group.
- LG1 represents a single bond or a divalent linking group.
- the divalent linking group includes an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an alkyleneoxy group (preferably an alkyleneoxy group having 1 to 12 carbon atoms), and an oxyalkylenecarbonyl group (preferably 1 to 12 carbon atoms).
- alkylene group preferably an alkylene group having 1 to 12 carbon atoms
- alkyleneoxy group preferably an alkyleneoxy group having 1 to 12 carbon atoms
- an oxyalkylenecarbonyl group preferably 1 to 12 carbon atoms.
- arylene group preferably arylene group having 6 to 20 carbon atoms
- RG4 represents a hydrogen atom or a substituent.
- the substituents include an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylthioether group, an arylthioether group, a heteroarylthioether group, an ethylenically unsaturated bond-containing group, and a cyclic ether.
- Examples include groups and blocked isocyanate groups.
- Examples of the ethylenically unsaturated bond-containing group include a vinyl group, a (meth) allyl group, and a (meth) acryloyl group.
- the cyclic ether group include an epoxy group and an oxetanyl group.
- the terminal structure of the graft chain is not particularly limited. It may be a hydrogen atom or a substituent.
- substituents include an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylthioether group, an arylthioether group, a heteroarylthioether group and the like.
- a group having a steric repulsion effect is preferable, and an alkyl group or an alkoxy group having 5 to 30 carbon atoms is preferable, from the viewpoint of improving the dispersibility of the pigment.
- the alkyl group and the alkoxy group may be linear, branched, or cyclic, and are preferably linear or branched.
- the graft chain means a molecular chain branched from the main chain. Further, the main chain means a molecular chain having the most branch points.
- the weight average molecular weight of the graft chain of the graft resin P-1 is preferably 500 to 30,000, more preferably 1,000 to 20,000, and even more preferably 2,000 to 10,000.
- the graft resin P-1 is preferably a resin containing a repeating unit represented by the formula (P-1-1).
- X 1 represents a trivalent linking group
- L 1 represents a single bond or a divalent linking group
- W 1 represents a polyester structure, a polyether structure and a poly (meth) acrylic. Represents a graft chain containing at least one structure selected from the structures.
- the trivalent linking group represented by X 1 includes a poly (meth) acrylic linking group, a polyalkyleneimine-based linking group, a polyester-based linking group, a polyurethane-based linking group, a polyurea-based linking group, a polyamide-based linking group, and a polyether.
- a poly (meth) acrylic linking group, a polyalkyleneimine-based linking group, a polyester-based linking group examples thereof include a system-based linking group and a polystyrene-based linking group, and a poly (meth) acrylic-based linking group, a polyalkyleneimine-based linking group and a polyester-based linking group are preferable, and a poly (meth) acrylic-based linking group is more preferable.
- an alkylene group, an arylene group, -O-, -CO-, -COO-, -OCO-, -NH-, -S-, and two or more of these are combined.
- the group is mentioned.
- the alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and even more preferably 1 to 15 carbon atoms.
- the alkylene group may be linear, branched or cyclic.
- the arylene group preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and even more preferably 6 to 10 carbon atoms.
- the alkylene group and the arylene group may have a substituent.
- Examples of the graft chain represented by W 1 include those described above, and the preferred range is also the same.
- the main chain of the graft resin P-1 preferably contains a repeating unit having at least one selected from an acid group, a basic group, or a pigment-like skeleton from the viewpoint of adsorption with a pigment.
- the acid group include a carboxy group, a sulfo group and a phosphoric acid group, and a carboxy group is preferable.
- the basic group include a group represented by the formula (a-1) and a group represented by the formula (a-2).
- pigment-like skeleton examples include aromatic rings (eg, phenyl, naphthyl) and heterocycles (eg, phenylmaleimide, naphthalimide, benzimidazole, benzimidazolone, anthraquinone, etc.).
- aromatic rings eg, phenyl, naphthyl
- heterocycles eg, phenylmaleimide, naphthalimide, benzimidazole, benzimidazolone, anthraquinone, etc.
- Ra 1 and Ra 2 each independently represent a hydrogen atom, an alkyl group or an aryl group, and Ra 1 and Ra 2 may be bonded to each other to form a ring;
- Ra 11 represents a hydrogen atom, a hydroxy group, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an acyl group or an oxyradic, and Ra 12 to Ra 19 are independent of each other.
- Hydrogen atom, alkyl group or aryl group Hydrogen atom, alkyl group or aryl group.
- the number of carbon atoms of the alkyl group represented by Ra 1 , Ra 2 , Ra 11 to Ra 19 is preferably 1 to 30, more preferably 1 to 15, further preferably 1 to 8, and particularly preferably 1 to 5.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched, and more preferably linear.
- the alkyl group may have a substituent.
- the aryl group represented by Ra 1 , Ra 2 , and Ra 11 to Ra 19 preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and even more preferably 6 to 12 carbon atoms.
- the aryl group may have a substituent.
- the number of carbon atoms of the alkoxy group represented by Ra 11 is preferably 1 to 30, more preferably 1 to 15, further preferably 1 to 8, and particularly preferably 1 to 5.
- the alkoxy group may have a substituent.
- the aryloxy group represented by Ra 11 preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and even more preferably 6 to 12 carbon atoms.
- the aryloxy group may have a substituent.
- the number of carbon atoms of the acyl group represented by Ra 11 is preferably 2 to 30, more preferably 2 to 20, and even more preferably 2 to 12.
- the acyl group may have a substituent.
- the main chain of the graft resin P-1 contains a repeating unit having a polymerizable group.
- the polymerizable group include an ethylenically unsaturated bond-containing group such as a vinyl group, a (meth) allyl group, and a (meth) acryloyl group.
- the weight average molecular weight of the graft resin P-1 is preferably 2000 to 50000, more preferably 3000 to 45000, and even more preferably 4000 to 40,000.
- the acid value of the graft resin P-1 is preferably 10 to 200 mgKOH / g, more preferably 20 to 150 mgKOH / g, still more preferably 30 to 120 mgKOH / g.
- the amine value of the graft resin P-1 is preferably 10 to 200 mgKOH / g, more preferably 20 to 150 mgKOH / g, still more preferably 30 to 120 mgKOH / g.
- graft resin P-1 examples include the dispersants B-1, B-2, B-3, B-4, B-6, B-7, B-8, and B- described in Examples described later. 9, B-10 and the like can be mentioned. Further, the resins described in paragraph numbers 0025 to 0094 of JP2012-255128, paragraphs 0022 to 0097 of JP2009-203462, and paragraph numbers 0102 to 0166 of JP2012-255128 are also mentioned. Be done.
- the block copolymer P-2 contains at least one structure selected from a polyester structure, a polyether structure and a poly (meth) acrylic structure.
- the polyester structure include structures represented by the above-mentioned formula (G-1), formula (G-4) or formula (G-5).
- the polyether structure include a structure represented by the above-mentioned formula (G-2).
- the poly (meth) acrylic structure include the structure represented by the above-mentioned formula (G-3).
- the block copolymer means a copolymer having a block of a plurality of polymers.
- the block copolymer P-2 is a polymer having a block of a polymer having a repeating unit containing an acid group or a basic group (hereinafter, also referred to as block A) and a polymer having a repeating unit not containing an acid group and a basic group. It is preferably a block copolymer with the block (hereinafter, also referred to as block B).
- block A a polymer having a repeating unit containing an acid group or a basic group
- block B a block copolymer with the block
- the acid group and the basic group those described in the above-mentioned graft resin P-1 can be mentioned, and the preferred range is also the same.
- At least one of the block A and the block B preferably contains at least one structure selected from a polyester structure, a polyether structure and a poly (meth) acrylic structure, and both the block A and the block B are a polyester structure and a poly. It is more preferable to include at least one structure selected from an ether structure and a poly (meth) acrylic structure, and it is further preferable that both block A and block B contain a poly (meth) acrylic structure.
- block A is preferably a block of a polymer having a repeating unit containing a basic group.
- At least one of block A and block B may contain a polymerizable group.
- the weight average molecular weight of the block copolymer P-2 is preferably 2000 to 50000, more preferably 3000 to 45000, and even more preferably 4000 to 40,000.
- the acid value of the block copolymer P-2 is preferably 10 to 200 mgKOH / g, more preferably 20 to 150 mgKOH / g, still more preferably 30 to 120 mgKOH / g. ..
- the amine value of the block copolymer P-2 is preferably 10 to 200 mgKOH / g, more preferably 20 to 150 mgKOH / g, and further preferably 30 to 120 mgKOH / g. preferable.
- block copolymer P-2 examples include the dispersant B-5 described in Examples described later.
- the block copolymer P-2 is described in the block copolymer (B) described in paragraphs 0063 to 0112 of JP2014-219665A and paragraphs 0046 to 0076 of JP-A-2018-156021.
- the block copolymer A1 which has been prepared can also be used, and the contents thereof are incorporated in the present specification.
- Resin P-3 is a resin having a structure in which at least one end of a polymer chain containing at least one structure selected from a polyester structure, a polyether structure and a poly (meth) acrylic structure is sealed with an acid group.
- the polyether structure include a structure represented by the above-mentioned formula (G-2).
- the poly (meth) acrylic structure include the structure represented by the above-mentioned formula (G-3).
- examples of the acid group that seals the end of the polymer chain include a carboxy group, a sulfo group, and a phosphoric acid group, and a phosphoric acid group is preferable.
- the resin P-3 is preferably a resin having a structure represented by the formula P-3-1.
- Rp 1 represents an alkylene group
- Rp 2 represents a hydrogen atom or a substituent
- n represents a number of 10 to 1000
- y represents a number of 1 to 2.
- the carbon number of the alkylene group represented by Rp 1 is preferably 1 to 10, more preferably 1 to 5, and even more preferably 2 or 3.
- Rp 1 is preferably an ethylene group.
- Examples of the substituent represented by Rp 2 include an alkyl group, an aryl group, a heteroaryl group and the like, and an alkyl group is preferable.
- the alkyl group preferably has 5 to 30 carbon atoms.
- the alkyl group may be linear, branched, or cyclic, preferably linear or branched, and more preferably branched.
- the weight average molecular weight of the resin P-3 is preferably 2000 to 50000, more preferably 3000 to 45000, and even more preferably 4000 to 40,000.
- the acid value of the resin P-3 is preferably 10 to 200 mgKOH / g, more preferably 20 to 150 mgKOH / g, and even more preferably 30 to 120 mgKOH / g.
- resin P-3 examples include dispersants B-11, B-12, B-13 and the like described in Examples described later.
- the coloring composition of the present invention can contain a resin other than the above-mentioned specific resin (hereinafter, also referred to as another resin).
- resins include (meth) acrylic resin, epoxy resin, en-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, and polyimide.
- resins include resins, polyamideimide resins, polyimine resins, polyolefin resins, cyclic olefin resins, polyester resins, styrene resins and the like.
- One of these resins may be used alone, or two or more thereof may be mixed and used.
- the weight average molecular weight (Mw) of the other resin is preferably 2000 to 2000000.
- the upper limit is preferably 1,000,000 or less, more preferably 500,000 or less.
- the lower limit is preferably 3000 or more, and more preferably 5000 or more.
- Alkali-soluble resin can be used as the other resin.
- the alkali-soluble resin include resins having an acid group.
- the type of acid group include a carboxy group, a phosphoric acid group, a sulfo group, and a phenolic hydroxy group.
- the resin having an acid group a resin in which an acid anhydride is reacted with a hydroxy group generated by epoxy ring opening and an acid group is introduced may be used. Examples of such a resin include the resin described in Japanese Patent No. 6349629.
- the resin having an acid group can also be used as a dispersant.
- the alkali-soluble resin the alkali-soluble resin described in JP-A-2017-173787 can also be used.
- the acid value of the alkali-soluble resin is preferably 30 to 500 mgKOH / g.
- the lower limit is preferably 50 mgKOH / g or more, and more preferably 70 mgKOH / g or more.
- the upper limit is preferably 400 mgKOH / g or less, more preferably 200 mgKOH / g or less, further preferably 150 mgKOH / g or less, and most preferably 120 mgKOH / g or less.
- the other resin contains a repeating unit derived from a compound represented by the formula (ED1) and / or a compound represented by the following formula (ED2) (hereinafter, these compounds may be referred to as "ether dimer"). Resin can be used.
- R 1 and R 2 each independently represent a hydrocarbon group having 1 to 25 carbon atoms which may have a hydrogen atom or a substituent.
- R represents a hydrogen atom or an organic group having 1 to 30 carbon atoms.
- the description in JP-A-2010-168539 can be referred to.
- paragraph number 0317 of JP2013-209760A can be referred to, and this content is incorporated in the present specification.
- a resin containing a repeating unit having a polymerizable group can be used as the other resin.
- R 1 represents a hydrogen atom or a methyl group
- R 21 and R 22 each independently represent an alkylene group
- n represents an integer of 0 to 15.
- the alkylene group represented by R 21 and R 22 preferably has 1 to 10 carbon atoms, more preferably 1 to 5 carbon atoms, further preferably 1 to 3 carbon atoms, and particularly preferably 2 or 3 carbon atoms.
- n represents an integer of 0 to 15, preferably an integer of 0 to 5, more preferably an integer of 0 to 4, and even more preferably an integer of 0 to 3.
- Examples of the compound represented by the formula (X) include ethylene oxide of paracumylphenol or propylene oxide-modified (meth) acrylate.
- Examples of commercially available products include Aronix M-110 (manufactured by Toagosei Co., Ltd.).
- a resin as a dispersant can also be used.
- the dispersant include an acidic dispersant (acidic resin) and a basic dispersant (basic resin).
- the acidic dispersant (acidic resin) represents a resin in which the amount of acid groups is larger than the amount of basic groups.
- the acidic dispersant (acidic resin) a resin having an acid group content of 70 mol% or more is preferable when the total amount of the acid group and the basic group is 100 mol%.
- the acid group of the acidic dispersant (acidic resin) is preferably a carboxy group.
- the acid value of the acidic dispersant (acidic resin) is preferably 10 to 105 mgKOH / g.
- the basic dispersant represents a resin in which the amount of basic groups is larger than the amount of acid groups.
- a resin in which the amount of basic groups exceeds 50 mol% is preferable when the total amount of the amount of acid groups and the amount of basic groups is 100 mol%.
- the basic group contained in the basic dispersant is preferably an amino group.
- the resin used as the dispersant it is also preferable that the resin has a structure in which a plurality of polymer chains are bonded to the core portion.
- examples of such resins include dendrimers (including radial polymers).
- Specific examples of the dendrimer include the polymer compounds C-1 to C-31 described in paragraphs 0196 to 0209 of JP2013-043962.
- the resin used as the dispersant is also preferably a resin containing a repeating unit having an ethylenically unsaturated bond-containing group in the side chain.
- the content of the repeating unit having an ethylenically unsaturated bond-containing group in the side chain is preferably 10 mol% or more, more preferably 10 to 80 mol%, and 20 to 70 in all the repeating units of the resin. It is more preferably mol%.
- the resin described in JP-A-2018-087939 can also be used as the dispersant.
- the content of the resin in the total solid content of the coloring composition is preferably 1 to 60% by mass.
- the lower limit is preferably 5% by mass or more, more preferably 10% by mass or more, further preferably 15% by mass or more, and particularly preferably 20% by mass or more.
- the upper limit is preferably 50% by mass or less, more preferably 40% by mass or less.
- the content of the specific resin in the total solid content of the coloring composition is preferably 1 to 60% by mass.
- the lower limit is preferably 5% by mass or more, more preferably 10% by mass or more, further preferably 15% by mass or more, and particularly preferably 20% by mass or more.
- the upper limit is preferably 50% by mass or less, more preferably 40% by mass or less.
- the content of the specific resin in the resin contained in the coloring composition is preferably 10% by mass or more, more preferably 20% by mass or more, and the content is 30% by mass or more. Is even more preferable.
- the content of the specific resin is preferably 10 to 100 parts by mass with respect to 100 parts by mass of the pigment.
- the lower limit is preferably 15 parts by mass or more, more preferably 20 parts by mass or more, and further preferably 25 parts by mass or more.
- the upper limit is preferably 60 parts by mass or less, more preferably 45 parts by mass or less, and further preferably 40 parts by mass or less.
- the coloring composition of the present invention may contain only one kind of resin, or may contain two or more kinds of resins. When two or more kinds of resins are contained, it is preferable that the total amount thereof is within the above range.
- the coloring composition of the present invention contains a solvent.
- the solvent is preferably an organic solvent.
- the organic solvent include ester-based solvents, ketone-based solvents, alcohol-based solvents, amide-based solvents, ether-based solvents, hydrocarbon-based solvents and the like.
- paragraph No. 0223 of International Publication No. 2015/166779 can be referred to, the contents of which are incorporated herein by reference.
- an ester solvent substituted with a cyclic alkyl group and a ketone solvent substituted with a cyclic alkyl group can also be preferably used.
- organic solvent examples include polyethylene glycol monomethyl ether, dichloromethane, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2 -Heptanone, 3-pentanone, 4-heptanone, cyclohexanone, 2-methylcyclohexanone, 3-methylcyclohexanone, 4-methylcyclohexanone, cycloheptanone, cyclooctanone, cyclohexyl acetate, cyclopentanone, ethylcarbitol acetate, butylcarbi Tall acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 3-methoxy-N, N-dimethylpropanamide, 3-butoxy-N, N-di
- aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) as organic solvents may need to be reduced for environmental reasons (for example, 50 parts by mass (parts) with respect to the total amount of organic solvent. Per millision) or less, 10 mass ppm or less, or 1 mass ppm or less).
- an organic solvent having a low metal content it is preferable to use an organic solvent having a low metal content, and the metal content of the organic solvent is preferably, for example, 10 mass ppb (parts per parts) or less. If necessary, an organic solvent at the mass ppt (parts per trillion) level may be used, and such an organic solvent is provided by, for example, Toyo Synthetic Co., Ltd. (The Chemical Daily, November 13, 2015). ..
- Examples of the method for removing impurities such as metals from the organic solvent include distillation (molecular distillation, thin film distillation, etc.) and filtration using a filter.
- the filter pore diameter of the filter used for filtration is preferably 10 ⁇ m or less, more preferably 5 ⁇ m or less, and even more preferably 3 ⁇ m or less.
- the filter material is preferably polytetrafluoroethylene, polyethylene or nylon.
- the organic solvent may contain isomers (compounds having the same number of atoms but different structures). Further, only one kind of isomer may be contained, or a plurality of kinds may be contained.
- the content of peroxide in the organic solvent is preferably 0.8 mmol / L or less, and more preferably substantially free of peroxide.
- the content of the solvent in the coloring composition is preferably 10 to 95% by mass, more preferably 20 to 90% by mass, and even more preferably 30 to 90% by mass.
- the coloring composition of the present invention does not substantially contain an environmentally regulated substance from the viewpoint of environmental regulations.
- substantially free of the environmentally regulated substance means that the content of the environmentally regulated substance in the coloring composition is 50 mass ppm or less, and preferably 30 mass ppm or less. It is more preferably 10 mass ppm or less, and particularly preferably 1 mass ppm or less.
- the environmentally regulated substance include benzene; alkylbenzenes such as toluene and xylene; and halogenated benzenes such as chlorobenzene.
- REACH Registration Evolution Analysis and Restriction of Chemicals
- PRTR Policy Release and Transfer Register
- VOC Volatile and Transfer Registor
- VOC Volatile Organic Compounds
- VOC Volatile Organic Compounds
- VOC Volatile Organic Compounds
- VOC Volatile Organic Compounds
- a method for reducing the environmentally regulated substance there is a method of heating or depressurizing the inside of the system to raise the boiling point of the environmentally regulated substance or higher and distilling off the environmentally regulated substance from the system to reduce the amount. Further, when distilling off a small amount of an environmentally regulated substance, it is also useful to azeotrope with a solvent having a boiling point equivalent to that of the corresponding solvent in order to improve efficiency.
- a polymerization inhibitor or the like is added and the mixture is distilled off under reduced pressure in order to prevent the radical polymerization reaction from proceeding and cross-linking between molecules during distillation under reduced pressure. May be.
- distillation methods are a stage of a raw material, a stage of a product obtained by reacting the raw materials (for example, a resin solution after polymerization or a polyfunctional monomer solution), or a stage of a coloring composition prepared by mixing these compounds. It is possible at any stage such as.
- the coloring composition of the present invention can contain a pigment derivative other than the above-mentioned compound S (hereinafter, also referred to as another pigment derivative).
- examples of other pigment derivatives include compounds having a structure in which an acid group or a basic group is bonded to a pigment skeleton.
- the pigment skeletons constituting the pigment derivatives include quinoline pigment skeleton, benzoimidazolone pigment skeleton, benzoisoindole pigment skeleton, benzothiazole pigment skeleton, inimium pigment skeleton, squarylium pigment skeleton, croconium pigment skeleton, oxonol pigment skeleton, and pyrolopyrrole pigment.
- Examples of the acid group include a sulfo group, a carboxy group, a phosphoric acid group and salts thereof.
- alkali metal ions Li + , Na + , K +, etc.
- alkaline earth metal ions Ca 2+ , Mg 2+, etc.
- ammonium ions imidazolium ions, pyridinium ions, etc.
- Examples include phosphonium ion.
- Examples of the basic group include an amino group, a salt of an ammonium group, and a phthalimidemethyl group.
- Examples of the atom or atomic group constituting the salt include hydroxide ion, halogen ion, carboxylic acid ion, sulfonic acid ion, and phenoxide ion.
- a pigment derivative having excellent visible transparency (hereinafter, also referred to as a transparent pigment derivative) can be contained.
- the maximum value of the molar extinction coefficient in the wavelength region of 400 ⁇ 700 nm of the transparent pigment derivative (.epsilon.max) is that it is preferable, 1000L ⁇ mol -1 ⁇ cm -1 or less is not more than 3000L ⁇ mol -1 ⁇ cm -1 Is more preferable, and 100 L ⁇ mol -1 ⁇ cm -1 or less is further preferable.
- the lower limit of ⁇ max is, for example, 1 L ⁇ mol -1 ⁇ cm -1 or more, and may be 10 L ⁇ mol -1 ⁇ cm -1 or more.
- pigment derivatives include the compounds described in Examples described later, JP-A-56-118462, JP-A-63-246674, JP-A-01-217777, JP-A-03-009961.
- Japanese Patent Application Laid-Open No. 03-026767 Japanese Patent Application Laid-Open No. 03-153780
- Japanese Patent Application Laid-Open No. 03-045662 Japanese Patent Application Laid-Open No. 04-285669
- Japanese Patent Application Laid-Open No. 06-145546 Japanese Patent Application Laid-Open No. 06-21288
- Japanese Patent Application Laid-Open No. 06-240158 Japanese Patent Application Laid-Open No. 10-030063
- the content of the other pigment derivative is preferably 30 parts by mass or less, more preferably 20 parts by mass or less, still more preferably 15 parts by mass or less, and 10 parts by mass with respect to 100 parts by mass of the pigment. It is particularly preferable that the amount is less than or equal to a part.
- the content of the other pigment derivative is preferably 0.01 to 100 parts by mass, more preferably 0.1 to 10 parts by mass, and 0.2 by mass with respect to 1 part by mass of the compound S. It is more preferably 5 parts by mass or less.
- the total content of the other pigment derivative and the above-mentioned compound S is preferably 1 to 30 parts by mass with respect to 100 parts by mass of the pigment.
- the lower limit is preferably 2 parts by mass or more, and more preferably 3 parts by mass or more.
- the upper limit is preferably 20 parts by mass or less, and more preferably 15 parts by mass or less. Only one kind of other pigment derivative may be used, or two or more kinds may be used in combination. When two or more types are used in combination, the total amount thereof is preferably in the above range.
- the coloring composition of the present invention can contain an infrared absorber.
- the infrared absorber is preferably a compound having a maximum absorption wavelength on the longer wavelength side than the wavelength of 700 nm.
- the infrared absorber is preferably a compound having a maximum absorption wavelength in the range of more than 700 nm and 1800 nm or less.
- the ratio A 1 / A 2 between the absorbance A 2 in the absorbance A 1 and the maximum absorption wavelength in the wavelength 500nm of the infrared absorbing agent is preferably 0.08 or less, and more preferably 0.04 or less ..
- Examples of the infrared absorber include pyrrolopyrrole compounds, cyanine compounds, squarylium compounds, phthalocyanine compounds, naphthalocyanine compounds, quaterylene compounds, merocyanine compounds, croconium compounds, oxonol compounds, iminium compounds, dithiol compounds, triarylmethane compounds, pyrromethene compounds and azomethine.
- Examples thereof include compounds, anthraquinone compounds, dibenzofuranone compounds, dithiolene metal complexes, metal oxides, metal boroides and the like.
- Examples of the pyrrolopyrrole compound include the compounds described in paragraphs 0016 to 0058 of JP2009-263614, the compounds described in paragraphs 0037-0052 of JP2011-066731A, and International Publication No. 2015/166783. Examples thereof include the compounds described in paragraphs 0010 to 0033.
- Examples of the squarylium compound include the compounds described in paragraphs 0044 to 0049 of JP2011-208101A, the compounds described in paragraphs 0060 to 0061 of Patent No. 6065169, and paragraph numbers 0040 of International Publication No. 2016/181987. , The compound described in JP-A-2015-176046, the compound described in paragraph No. 0072 of International Publication No.
- JP2012-077153 the oxytitanium phthalocyanine described in JP2006-343631, and paragraphs 0013 to 0029 of JP2013-195480.
- Examples of the naphthalocyanine compound include the compounds described in paragraph No. 0093 of JP2012-07715A.
- Examples of the dithiolene metal complex include the compounds described in Japanese Patent No. 5733804.
- the metal oxide include indium tin oxide, antimonthine oxide, zinc oxide, Al-doped zinc oxide, fluorine-doped tin dioxide, niobium-doped titanium dioxide, tungsten oxide and the like.
- tungsten oxide paragraph number 0080 of JP-A-2016-006476 can be referred to, and the contents thereof are incorporated in the present specification.
- the metal boride include lanthanum hexaboride.
- examples of commercially available lanthanum hexaboride products include LaB 6- F (manufactured by Nippon Shinkinzoku Co., Ltd.).
- the compound described in International Publication No. 2017/11394 can also be used.
- examples of commercially available indium tin oxide products include F-ITO (manufactured by DOWA Hi-Tech Co., Ltd.).
- Examples of the infrared absorber include a squarylium compound described in JP-A-2017-197437, a squarylium compound described in JP-A-2017-025311, a squarylium compound described in International Publication No. 2016/154782, and Patent No. 5884953.
- Squarylium compound described in Japanese Patent Publication No. 6036689 Squalylium compound described in Japanese Patent No. 581604, Squalylium compound described in International Publication No. 2017/213047, Squarylium compound described in paragraphs 0090 to 0107 of International Publication No. 2017/213047, The pyrrole ring-containing compound described in paragraphs 0019 to 0075 of Japanese Patent Application Laid-Open No.
- Concatenated squalylium compound compound having a pyrrolbis-type squalylium skeleton or croconium skeleton described in JP-A-2017-141215, dihydrocarbazole-type squarylium compound described in JP-A-2017-082029, JP-A-2017-066120
- the asymmetric compound described in paragraphs 0027 to 0114 of Japanese Patent Application Laid-Open No. 2017-067963, the pyrrol ring-containing compound (carbazole type) described in Japanese Patent Application Laid-Open No. 2017-067963, the phthalocyanine compound described in Japanese Patent No. 6251530, and the like are used. You can also do it.
- the content of the infrared absorber in the total solid content of the coloring composition is preferably 1 to 40% by mass.
- the lower limit is preferably 2% by mass or more, more preferably 5% by mass or more, and further preferably 10% by mass or more.
- the upper limit is preferably 30% by mass or less, more preferably 25% by mass or less.
- the coloring composition of the present invention may contain only one kind of infrared absorber, or may contain two or more kinds of infrared absorbers. When two or more kinds of infrared absorbers are contained, it is preferable that the total amount thereof is within the above range.
- the coloring composition of the present invention can contain a polymerizable compound.
- a polymerizable compound a known compound that can be crosslinked by radicals, acids or heat can be used.
- the polymerizable compound is preferably, for example, a compound having an ethylenically unsaturated bond-containing group.
- the ethylenically unsaturated bond-containing group include a vinyl group, a (meth) allyl group, and a (meth) acryloyl group.
- the polymerizable compound used in the present invention is preferably a radically polymerizable compound.
- the polymerizable compound may be in any chemical form such as a monomer, a prepolymer or an oligomer, but a monomer is preferable.
- the molecular weight of the polymerizable compound is preferably 100 to 3000.
- the upper limit is more preferably 2000 or less, and even more preferably 1500 or less.
- the lower limit is more preferably 150 or more, and even more preferably 250 or more.
- the polymerizable compound is preferably a compound containing 3 or more ethylenically unsaturated bond-containing groups, more preferably a compound containing 3 to 15 ethylenically unsaturated bond-containing groups, and more preferably an ethylenically unsaturated bond. It is more preferable that the compound contains 3 to 6 containing groups. Further, the polymerizable compound is preferably a (meth) acrylate compound having 3 to 15 functionalities, and more preferably a (meth) acrylate compound having 3 to 6 functionalities.
- polymerizable compound examples include paragraph numbers 0995 to 0108 of JP2009-288705, paragraphs 0227 of JP2013-029760, paragraphs 0254 to 0257 of JP2008-292970, and JP-A.
- the compounds described in paragraph numbers 0034 to 0038 of Japanese Patent Application Laid-Open No. 2013-253224, paragraph numbers 0477 of Japanese Patent Application Laid-Open No. 2012-208494, Japanese Patent Application Laid-Open No. 2017-048637, Japanese Patent No. 6057891 and Japanese Patent Application Laid-Open No. 6031807 are These contents are incorporated herein by reference.
- Examples of the polymerizable compound include dipentaerythritol triacrylate (commercially available KAYARAD D-330; manufactured by Nippon Kayaku Co., Ltd.) and dipentaerythritol tetraacrylate (commercially available KAYARAD D-320; Nihon Kayaku Co., Ltd.).
- diglycerin EO ethylene oxide modified (meth) acrylate
- pentaerythritol tetraacrylate manufactured by Shin-Nakamura Chemical Industry Co., Ltd., NK ester A
- 1,6-hexanediol diacrylate manufactured by Nippon Kayaku Co., Ltd., KAYARAD HDDA
- RP-1040 manufactured by Nippon Kayaku Co., Ltd.
- Aronix TO-2349 manufactured by Toa Synthetic Co., Ltd.
- NK Oligo UA-7200 manufactured by Shin-Nakamura Chemical Industry Co., Ltd.
- DPHA-40H manufactured by Nippon Kayaku Co., Ltd.
- the polymerizable compounds include trimethylolpropane tri (meth) acrylate, trimethylolpropane propyleneoxy-modified tri (meth) acrylate, trimethylolpropane ethyleneoxy-modified tri (meth) acrylate, and isocyanuric acid ethyleneoxy-modified tri (meth).
- Trifunctional (meth) acrylate compounds such as acrylate and pentaerythritol tri (meth) acrylate can also be used.
- Commercially available trifunctional (meth) acrylate compounds include Aronix M-309, M-310, M-321, M-350, M-360, M-313, M-315, M-306, and M-305.
- M-303, M-452, M-450 manufactured by Toagosei Co., Ltd.
- a compound having an acid group can also be used as the polymerizable compound.
- the polymerizable compound having an acid group By using a polymerizable compound having an acid group, the polymerizable compound in the unexposed portion can be easily removed during development, and the generation of development residue can be suppressed.
- the acid group include a carboxy group, a sulfo group, a phosphoric acid group and the like, and a carboxy group is preferable.
- the polymerizable compound having an acid group include succinic acid-modified dipentaerythritol penta (meth) acrylate.
- Examples of commercially available products of the polymerizable compound having an acid group include Aronix M-510, M-520, and Aronix TO-2349 (manufactured by Toagosei Co., Ltd.).
- the preferable acid value of the polymerizable compound having an acid group is 0.1 to 40 mgKOH / g, and more preferably 5 to 30 mgKOH / g.
- the acid value of the polymerizable compound is 0.1 mgKOH / g or more, the solubility in a developing solution is good, and when the acid value is 40 mgKOH / g or less, it is advantageous in production and handling.
- a compound having a caprolactone structure can also be used.
- examples of commercially available products of the polymerizable compound having a caprolactone structure include KAYARAD DPCA-20, DPCA-30, DPCA-60, DPCA-120 (all manufactured by Nippon Kayaku Co., Ltd.) and the like.
- a polymerizable compound having an alkyleneoxy group can also be used.
- a polymerizable compound having an ethyleneoxy group and / or a propyleneoxy group is preferable, a polymerizable compound having an ethyleneoxy group is more preferable, and 3 to 3 having 4 to 20 ethyleneoxy groups.
- a hexafunctional (meth) acrylate compound is more preferred.
- Commercially available products of the polymerizable compound having an alkyleneoxy group include SR-494, which is a tetrafunctional (meth) acrylate having four ethyleneoxy groups manufactured by Sartmer, and a trifunctional (meth) having three isobutyleneoxy groups. ) KAYARAD TPA-330, which is an acrylate, and the like.
- a polymerizable compound having a fluorene skeleton can also be used.
- examples of commercially available products of the polymerizable compound having a fluorene skeleton include Ogsol EA-0200 and EA-0300 (manufactured by Osaka Gas Chemical Co., Ltd., a (meth) acrylate monomer having a fluorene skeleton).
- the polymerizable compound it is also preferable to use a compound that does not substantially contain an environmentally regulatory substance such as toluene.
- an environmentally regulatory substance such as toluene.
- commercially available products of such compounds include KAYARAD DPHA LT and KAYARAD DPEA-12 LT (manufactured by Nippon Kayaku Co., Ltd.).
- the content of the polymerizable compound in the total solid content of the coloring composition is preferably 0.1 to 50% by mass.
- the lower limit is more preferably 0.5% by mass or more, further preferably 1% by mass or more.
- the upper limit is more preferably 45% by mass or less, further preferably 40% by mass or less.
- the polymerizable compound may be used alone or in combination of two or more. When two or more types are used in combination, it is preferable that the total of them is within the above range.
- the coloring composition of the present invention can contain a polymerization initiator.
- the polymerization initiator include a photopolymerization initiator, a thermal polymerization initiator and the like, and a photopolymerization initiator is preferable. Further, the polymerization initiator is preferably a radical polymerization initiator.
- thermal polymerization initiator examples include 2,2'-azobisisobutyronitrile (AIBN), 3-carboxypropionitrile, azobismalononitrile, and dimethyl- (2,2') -azobis (2-methyl).
- AIBN 2,2'-azobisisobutyronitrile
- 3-carboxypropionitrile examples include azo compounds such as propionate), tert-butylperoxybenzoate, benzoyl peroxide, lauroyl peroxide, and organic peroxides such as potassium persulfate.
- photopolymerization initiator examples include halogenated hydrocarbon derivatives (for example, compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazoles, oxime compounds, organic peroxides, and thio compounds. , Ketone compounds, aromatic onium salts, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds and the like.
- the photopolymerization initiator is a trihalomethyltriazine compound, a benzyldimethylketal compound, an ⁇ -hydroxyketone compound, an ⁇ -aminoketone compound, an acylphosphine compound, a phosphine oxide compound, a metallocene compound, an oxime compound, or a triarylimidazole.
- It is preferably a dimer, an onium compound, a benzothiazole compound, a benzophenone compound, an acetophenone compound, a cyclopentadiene-benzene-iron complex, a halomethyloxadiazole compound and a 3-aryl substituted coumarin compound, preferably an oxime compound and an ⁇ -hydroxyketone compound.
- ⁇ -Aminoketone compound, and a compound selected from an acylphosphine compound are more preferable, and an oxime compound is further preferable.
- photopolymerization initiator the compound described in paragraphs 0065 to 0111 of JP-A-2014-130173 and JP-A-6301489, MATERIAL STAGE 37-60p, vol. 19, No. 3, 2019 Peroxide-based Photopolymerization Initiator, International Publication No. 2018/221177, Photopolymerization Initiator, International Publication No. 2018/110179, Photopolymerization Initiator, JP-A-2019-043864. Examples thereof include the photopolymerization initiator described in JP-A-2019-044030, and the contents thereof are incorporated in the present specification.
- ⁇ -hydroxyketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (above, IGM Resins B.V.), Irgacure 184, Irgacure 1173, Irgacure27, Irgacure29. (Manufactured by the company) and the like.
- Commercially available ⁇ -aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (above, IGM Resins BV), Irgacure 907, Irgacure 369, Irgacure 369, Irger Made) and so on.
- acylphosphine compounds examples include Omnirad 819, Omnirad TPO (above, manufactured by IGM Resins BV), Irgacure 819, and Irgacure TPO (above, manufactured by BASF).
- Examples of the oxime compound include the compound described in JP-A-2001-233842, the compound described in JP-A-2000-080068, the compound described in JP-A-2006-342166, and J. Am. C. S. The compound according to Perkin II (1979, pp. 1653-1660), J. Mol. C. S. The compound described in Perkin II (1979, pp. 156-162), the compound described in Journal of Photopolisr Science and Technology (1995, pp. 202-232), the compound described in JP-A-2000-066385, the compound described in JP-A-2000-066385. Compounds described in JP-A-2004-534797, compounds described in JP-A-2017-109766, compounds described in Japanese Patent No.
- oxime compound examples include 3-benzoyloxyiminobutane-2-one, 3-acetoxyiminovtan-2-one, 3-propionyloxyiminobutane-2-one, 2-acetoxyiminopentane-3-one, and the like.
- 2-acetoxyimino-1-phenylpropane-1-one 2-benzoyloxyimino-1-phenylpropane-1-one, 3- (4-toluenesulfonyloxy) iminobutane-2-one, and 2-ethoxycarbonyloxy Examples thereof include imino-1-phenylpropane-1-one.
- an oxime compound having a fluorene ring can also be used.
- Specific examples of the oxime compound having a fluorene ring include the compounds described in JP-A-2014-137466.
- an oxime compound having a skeleton in which at least one benzene ring of the carbazole ring is a naphthalene ring can also be used.
- Specific examples of such an oxime compound include the compounds described in International Publication No. 2013/083505.
- an oxime compound having a fluorine atom can also be used as the photopolymerization initiator.
- Specific examples of the oxime compound having a fluorine atom are described in the compounds described in JP-A-2010-262028, compounds 24, 36-40 described in JP-A-2014-500852, and JP-A-2013-164471.
- Compound (C-3) and the like can be mentioned.
- an oxime compound having a nitro group can be used as the photopolymerization initiator.
- the oxime compound having a nitro group is also preferably a dimer.
- Specific examples of the oxime compound having a nitro group include the compounds described in paragraphs 0031 to 0047 of JP2013-114249A and paragraphs 0008-0012 and 0070-0079 of JP-A-2014-137466. Examples thereof include the compound described in paragraphs 0007 to 0025 of Japanese Patent No. 4223071, ADEKA ARCULDS NCI-831 (manufactured by ADEKA Corporation).
- an oxime compound having a benzofuran skeleton can also be used.
- Specific examples include OE-01 to OE-75 described in International Publication No. 2015/036910.
- an oxime compound in which a substituent having a hydroxy group is bonded to the carbazole skeleton can also be used.
- Examples of such a photopolymerization initiator include the compounds described in International Publication No. 2019/088055.
- an oxime compound having an aromatic ring group Ar OX1 having an electron-attracting group introduced into the aromatic ring (hereinafter, also referred to as oxime compound OX) can also be used.
- the electron-attracting group of the aromatic ring group Ar OX1 include an acyl group, a nitro group, a trifluoromethyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group and a cyano group.
- the benzoyl group may have a substituent.
- the substituent include a halogen atom, a cyano group, a nitro group, a hydroxy group, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a heterocyclic group, a heterocyclic oxy group, an alkenyl group, an alkylsulfanyl group and an arylsulfanyl group.
- an acyl group or an amino group more preferably an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a heterocyclic oxy group, an alkylsulfanyl group, an arylsulfanyl group or an amino group, and more preferably an alkoxy group or an alkyl group. It is more preferably a sulfanyl group or an amino group.
- the oxime compound OX is preferably at least one selected from the compound represented by the formula (OX1) and the compound represented by the formula (OX2), and more preferably the compound represented by the formula (OX2). preferable.
- RX1 is an alkyl group, an alkenyl group, an alkoxy group, an aryl group, an aryloxy group, a heterocyclic group, a heterocyclic oxy group, an alkylsulfanyl group, an arylsulfanyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group.
- RX2 contains an alkyl group, an alkenyl group, an alkoxy group, an aryl group, an aryloxy group, a heterocyclic group, a heterocyclic oxy group, an alkylsulfanyl group, an arylsulfanyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group and an aryl.
- R X3 ⁇ R X14 represents a hydrogen atom or a substituent independently; Provided that at least one of R X10 ⁇ R X14 is an electron withdrawing group.
- R X12 is an electron withdrawing group, it is preferred that R X10, R X11, R X13 , R X14 is a hydrogen atom.
- oxime compound OX include the compounds described in paragraphs 0083 to 0105 of Japanese Patent No. 4600600.
- the oxime compound is preferably a compound having a maximum absorption wavelength in the wavelength range of 350 to 500 nm, and more preferably a compound having a maximum absorption wavelength in the wavelength range of 360 to 480 nm.
- the molar extinction coefficient of the oxime compound at a wavelength of 365 nm or a wavelength of 405 nm is preferably high, more preferably 1000 to 300,000, still more preferably 2000 to 300,000, and more preferably 5000 to 200,000. It is particularly preferable to have.
- the molar extinction coefficient of a compound can be measured using a known method. For example, it is preferable to measure at a concentration of 0.01 g / L using ethyl acetate with a spectrophotometer (Cary-5 spectrophotometer manufactured by Varian).
- Irgacure OXE01 manufactured by BASF
- Irgacure OXE02 manufactured by BASF
- Omnirad 2959 manufactured by IGM Resins BV
- a bifunctional or trifunctional or higher photoradical polymerization initiator may be used as the photopolymerization initiator.
- two or more radicals are generated from one molecule of the photoradical polymerization initiator, so that good sensitivity can be obtained.
- the crystallinity is lowered, the solubility in a solvent or the like is improved, the precipitation is less likely to occur with time, and the stability of the colored composition with time can be improved.
- Specific examples of the bifunctional or trifunctional or higher functional photo-radical polymerization initiators include Japanese Patent Publication No. 2010-527339, Japanese Patent Publication No. 2011-524436, International Publication No.
- the content of the polymerization initiator in the total solid content of the coloring composition is preferably 0.1 to 30% by mass.
- the lower limit is preferably 0.5% by mass or more, more preferably 1% by mass or more.
- the upper limit is preferably 20% by mass or less, more preferably 15% by mass or less.
- only one type of polymerization initiator may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount thereof is within the above range.
- the coloring composition of the present invention can contain a compound having a cyclic ether group.
- the cyclic ether group include an epoxy group and an oxetanyl group.
- the compound having a cyclic ether group is preferably a compound having an epoxy group (hereinafter, also referred to as an epoxy compound). Examples of the epoxy compound are described in paragraphs 0034 to 0036 of JP2013-011869, paragraph numbers 0147 to 0156 of JP2014-043556, and paragraph numbers 0083 to 0092 of JP2014-089408. Compounds, compounds described in JP-A-2017-179172 can also be used. These contents are incorporated herein.
- the epoxy compound may be a low molecular weight compound (for example, a molecular weight of less than 2000, further, a molecular weight of less than 1000), or a polymer compound (for example, a molecular weight of 1000 or more, and in the case of a polymer, a weight average molecular weight of 1000 or more). It may be any of.
- the weight average molecular weight of the epoxy compound is preferably 200 to 100,000, more preferably 500 to 50,000.
- the upper limit of the weight average molecular weight is preferably 10,000 or less, more preferably 5000 or less, and even more preferably 3000 or less.
- an epoxy resin can be preferably used as the epoxy compound.
- the epoxy resin include an epoxy resin which is a glycidyl etherified product of a phenol compound, an epoxy resin which is a glycidyl etherified product of various novolak resins, an alicyclic epoxy resin, an aliphatic epoxy resin, a heterocyclic epoxy resin, and a glycidyl ester.
- Examples thereof include a copolymer with another polymerizable unsaturated compound.
- the epoxy equivalent of the epoxy resin is preferably 310 to 3300 g / eq, more preferably 310 to 1700 g / eq, and even more preferably 310 to 1000 g / eq.
- EHPE3150 manufactured by Daicel Corporation
- EPICLON N-695 manufactured by DIC Corporation
- Marproof G-0150M G-0105SA, G-0130SP, G. -0250SP, G-1005S, G-1005SA, G-1010S, G-2050M, G-01100, G-01758 (all manufactured by NOF CORPORATION, epoxy group-containing polymer) and the like can be mentioned.
- the content of the compound having a cyclic ether group in the total solid content of the coloring composition is preferably 0.1 to 20% by mass.
- the lower limit is, for example, preferably 0.5% by mass or more, and more preferably 1% by mass or more.
- the upper limit is, for example, preferably 15% by mass or less, and more preferably 10% by mass or less.
- the compound having a cyclic ether group may be only one kind or two or more kinds. In the case of two or more types, it is preferable that the total amount thereof is within the above range.
- the coloring composition of the present invention may contain a curing accelerator.
- the curing accelerator include thiol compounds, methylol compounds, amine compounds, phosphonium salt compounds, amidin salt compounds, amide compounds, base generators, isocyanate compounds, alkoxysilane compounds, onium salt compounds and the like.
- Specific examples of the curing accelerator include the compound described in paragraph Nos. 0094 to 0097 of International Publication No. 2018/056189, the compound described in paragraph numbers 0246 to 0253 of JP-A-2015-034963, and JP-A-2013-041165.
- the coloring composition of the present invention can contain an ultraviolet absorber.
- an ultraviolet absorber a conjugated diene compound, an aminodiene compound, a salicylate compound, a benzophenone compound, a benzotriazole compound, an acrylonitrile compound, a hydroxyphenyltriazine compound, an indole compound, a triazine compound and the like can be used. Examples of such compounds include paragraph numbers 0038 to 0052 of JP2009-217221A, paragraph numbers 0052 to 0072 of JP2012-208374A, and paragraph numbers 0317 to 0334 of JP2013-066814.
- UV absorbers include UV-503 (conjugated diene compound manufactured by Daito Kagaku Co., Ltd.), TINUVIN 400, TINUVIN 405, TINUVIN 460, TINUVIN 477, TINUVIN 479 (above, triazine compound manufactured by BASF), etc.
- TINUVIN PS TINUVIN 99-2, TINUVIN 109, TINUVIN 326, TINUVIN 328, TINUVIN 384-2, TINUVIN 900, TINUVIN 928, TINUVIN 171, TINUVIN 1130 (above, BASF, benzotriazole compound), Adecastab Examples thereof include ADEKA Co., Ltd., benzotriazole compound), Ubinal A, Ubinal 3049, Ubinal 3050 (above, BASF Co., Ltd., benzophenone compound), Sumisorb130 (Suika Chemtex Co., Ltd., benzophenone compound) and the like.
- benzotriazole compound examples include the MYUA series made of Miyoshi Oil & Fat (The Chemical Daily, February 1, 2016). Further, as the ultraviolet absorber, the compounds described in paragraphs 0049 to 0059 of Japanese Patent No. 6268967 can also be used.
- the content of the ultraviolet absorber in the total solid content of the coloring composition is preferably 0.01 to 10% by mass, more preferably 0.01 to 5% by mass.
- only one kind of ultraviolet absorber may be used, or two or more kinds may be used.
- the total amount is preferably in the above range.
- the coloring composition of the present invention can contain a polymerization inhibitor.
- the polymerization inhibitor include hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4'-thiobis (3-methyl-6-tert-butylphenol), and the like.
- examples thereof include 2,2'-methylenebis (4-methyl-6-t-butylphenol) and N-nitrosophenylhydroxyamine salts (ammonium salt, first cerium salt, etc.). Of these, p-methoxyphenol is preferable.
- the content of the polymerization inhibitor in the total solid content of the coloring composition is preferably 0.0001 to 5% by mass.
- the polymerization inhibitor may be only one kind or two or more kinds. In the case of two or more types, it is preferable that the total amount is within the above range.
- the coloring composition of the present invention can contain a silane coupling agent.
- the silane coupling agent means a silane compound having a hydrolyzable group and other functional groups.
- the hydrolyzable group refers to a substituent that is directly linked to a silicon atom and can form a siloxane bond by at least one of a hydrolysis reaction and a condensation reaction.
- the hydrolyzable group include a halogen atom, an alkoxy group, an acyloxy group and the like, and an alkoxy group is preferable. That is, the silane coupling agent is preferably a compound having an alkoxysilyl group.
- Examples of the functional group other than the hydrolyzable group include a vinyl group, a (meth) allyl group, a (meth) acryloyl group, a mercapto group, an epoxy group, an oxetanyl group, an amino group, a ureido group, a sulfide group and an isocyanate group.
- a phenyl group and the like preferably an amino group, a (meth) acryloyl group and an epoxy group.
- silane coupling agent examples include N- ⁇ -aminoethyl- ⁇ -aminopropylmethyldimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-602), N- ⁇ -aminoethyl- ⁇ -amino.
- Propyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-603), N- ⁇ -aminoethyl- ⁇ -aminopropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBE-602), ⁇ -Aminopropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-903), ⁇ -aminopropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBE-903), 3-methacryloxy There are propylmethyldimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-502), 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co
- silane coupling agent examples include the compounds described in paragraphs 0018 to 0036 of JP2009-288703 and the compounds described in paragraphs 0056 to 0066 of JP2009-242604A. , These contents are incorporated herein.
- the content of the silane coupling agent in the total solid content of the coloring composition is preferably 0.01 to 15.0% by mass, more preferably 0.05 to 10.0% by mass.
- the silane coupling agent may be only one kind or two or more kinds. In the case of two or more types, it is preferable that the total amount is within the above range.
- the coloring composition of the present invention can contain a surfactant.
- a surfactant various surfactants such as a fluorine-based surfactant, a nonionic surfactant, a cationic surfactant, an anionic surfactant, and a silicone-based surfactant can be used.
- the surfactant described in paragraph Nos. 0238 to 0245 of International Publication No. 2015/166779 is mentioned, and the content thereof is incorporated in the present specification.
- the surfactant is preferably a fluorine-based surfactant.
- a fluorine-based surfactant in the coloring composition, the liquid characteristics (particularly, fluidity) can be further improved, and the liquid saving property can be further improved. It is also possible to form a film having a small thickness unevenness.
- the fluorine content in the fluorine-based surfactant is preferably 3 to 40% by mass, more preferably 5 to 30% by mass, and particularly preferably 7 to 25% by mass.
- a fluorine-based surfactant having a fluorine content within this range is effective in terms of uniformity in the thickness of the coating film and liquid saving, and has good solubility in a coloring composition.
- fluorine-based surfactant examples include the surfactants described in paragraphs 0060 to 0064 of Japanese Patent Laid-Open No. 2014-041318 (paragraphs 0060 to 0064 of International Publication No. 2014/017669) and the like, Japanese Patent Application Laid-Open No. 2011-.
- the surfactants described in paragraphs 0117 to 0132 of Japanese Patent Application Laid-Open No. 132503 and the surfactants described in JP-A-2020-008634 are mentioned, and the contents thereof are incorporated in the present specification.
- fluorine-based surfactants include, for example, Megafax F-171, F-172, F-173, F-176, F-177, F-141, F-142, F-143, F-144. , F-437, F-475, F-477, F-479, F-482, F-554, F-555-A, F-556, F-557, F-558, F-559, F-560.
- the fluorine-based surfactant has a molecular structure having a functional group containing a fluorine atom, and an acrylic compound in which a portion of the functional group containing a fluorine atom is cut off and the fluorine atom volatilizes when heat is applied.
- a fluorine-based surfactant include the Megafuck DS series manufactured by DIC Corporation (The Chemical Daily (February 22, 2016), Nikkei Sangyo Shimbun (February 23, 2016)), for example, Mega. Fuck DS-21 can be mentioned.
- fluorine-based surfactant it is also preferable to use a polymer of a fluorine atom-containing vinyl ether compound having a fluorinated alkyl group or a fluorinated alkylene ether group and a hydrophilic vinyl ether compound.
- a fluorine-based surfactant include the fluorine-based surfactants described in JP-A-2016-216602, the contents of which are incorporated in the present specification.
- the fluorine-based surfactant a block polymer can also be used.
- the fluorine-based surfactant has a repeating unit derived from a (meth) acrylate compound having a fluorine atom and 2 or more (preferably 5 or more) alkyleneoxy groups (preferably ethyleneoxy groups and propyleneoxy groups) (meth).
- a fluorine-containing polymer compound containing a repeating unit derived from an acrylate compound can also be preferably used.
- the fluorine-containing surfactants described in paragraphs 0016 to 0037 of JP-A-2010-032698 and the following compounds are also exemplified as the fluorine-based surfactants used in the present invention.
- the weight average molecular weight of the above compounds is preferably 3000 to 50,000, for example 14000.
- % indicating the ratio of the repeating unit is mol%.
- a fluorine-based surfactant a fluorine-containing polymer having an ethylenically unsaturated bond-containing group in the side chain can also be used. Specific examples thereof include the compounds described in paragraphs 0050 to 0090 and 0289 to 0295 of JP2010-164965, Megafuck RS-101, RS-102, RS-718K, manufactured by DIC Corporation. RS-72-K and the like can be mentioned. Further, as the fluorine-based surfactant, the compounds described in paragraphs 0015 to 0158 of JP-A-2015-117327 can also be used.
- Nonionic surfactants include glycerol, trimethylolpropane, trimethylolethane and their ethoxylates and propoxylates (eg, glycerol propoxylate, glycerol ethoxylate, etc.), polyoxyethylene lauryl ethers, polyoxyethylene stearyl ethers, etc.
- silicone-based surfactant examples include Torre Silicone DC3PA, Torre Silicone SH7PA, Torre Silicone DC11PA, Torre Silicone SH21PA, Torre Silicone SH28PA, Torre Silicone SH29PA, Torre Silicone SH30PA, Torre Silicone SH8400 (all, Toray Dow Corning Co., Ltd.). ), TSF-4440, TSF-4300, TSF-4445, TSF-4460, TSF-4452 (above, manufactured by Momentive Performance Materials), KP-341, KF-6001, KF-6002 (above, (Shinetsu Silicone Co., Ltd.), BYK307, BYK323, BYK330 (all manufactured by Big Chemie) and the like.
- the content of the surfactant in the total solid content of the coloring composition is preferably 0.001% by mass to 5.0% by mass, more preferably 0.005 to 3.0% by mass.
- the surfactant may be only one kind or two or more kinds. In the case of two or more types, it is preferable that the total amount is within the above range.
- the coloring composition of the present invention can contain an antioxidant.
- the antioxidant include a phenol compound, a phosphite ester compound, a thioether compound and the like.
- the phenol compound any phenol compound known as a phenolic antioxidant can be used.
- Preferred phenolic compounds include hindered phenolic compounds.
- a compound having a substituent at a site (ortho position) adjacent to the phenolic hydroxy group is preferable.
- a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms is preferable.
- the antioxidant a compound having a phenol group and a phosphite ester group in the same molecule is also preferable. Further, as the antioxidant, a phosphorus-based antioxidant can also be preferably used. Further, as the antioxidant, the compound described in Korean Patent Publication No. 10-2019-0059371 can also be used.
- the content of the antioxidant in the total solid content of the coloring composition is preferably 0.01 to 20% by mass, more preferably 0.3 to 15% by mass. Only one kind of antioxidant may be used, or two or more kinds may be used. When two or more types are used, the total amount is preferably in the above range.
- the coloring composition of the present invention may be used as a sensitizer, a curing accelerator, a filler, a thermosetting accelerator, a plasticizer and other auxiliary agents (for example, conductive particles, a filler, a defoaming agent, etc.), if necessary. It may contain a flame retardant, a leveling agent, a peeling accelerator, a fragrance, a surface tension adjusting agent, a chain transfer agent, etc.). By appropriately containing these components, properties such as film physical characteristics can be adjusted. These components are described in, for example, paragraph No. 0183 or later of JP2012-003225A (paragraph number 0237 of the corresponding US Patent Application Publication No. 2013/0034812), paragraph 2008-250074.
- the coloring composition of the present invention may contain a latent antioxidant, if necessary.
- the latent antioxidant is a compound in which the site that functions as an antioxidant is protected by a protecting group, and is heated at 100 to 250 ° C. or at 80 to 200 ° C. in the presence of an acid / base catalyst. This includes compounds in which the protecting group is desorbed and functions as an antioxidant.
- Examples of the latent antioxidant include compounds described in International Publication No. 2014/021023, International Publication No. 2017/030005, and JP-A-2017-008219.
- Examples of commercially available products of latent antioxidants include ADEKA ARKULS GPA-5001 (manufactured by ADEKA Corporation) and the like.
- the coloring composition of the present invention may contain a metal oxide in order to adjust the refractive index of the obtained film.
- the metal oxide include TiO 2 , ZrO 2 , Al 2 O 3 , SiO 2 and the like.
- the primary particle size of the metal oxide is preferably 1 to 100 nm, more preferably 3 to 70 nm, still more preferably 5 to 50 nm.
- the metal oxide may have a core-shell structure. Further, in this case, the core portion may be hollow.
- the coloring composition of the present invention may contain a light resistance improving agent.
- the light resistance improving agent include the compounds described in paragraphs 0036 to 0037 of JP-A-2017-198787, the compounds described in paragraphs 0029 to 0034 of JP-A-2017-146350, and JP-A-2017-129774.
- the use of perfluoroalkyl sulfonic acid and its salt, and perfluoroalkyl carboxylic acid and its salt may be restricted.
- the perfluoroalkyl sulfonic acid particularly the perfluoroalkyl sulfonic acid having 6 to 8 carbon atoms in the perfluoroalkyl group
- a salt thereof and a par
- the content of the fluoroalkylcarboxylic acid (particularly the perfluoroalkylcarboxylic acid having 6 to 8 carbon atoms in the perfluoroalkyl group) and its salt is 0.01 ppb to 1,000 ppb with respect to the total solid content of the coloring composition.
- the coloring composition of the present invention may be substantially free of perfluoroalkyl sulfonic acid and salts thereof, as well as perfluoroalkyl carboxylic acid and salts thereof.
- perfluoroalkyl sulfonic acid and its salt by using a compound that can substitute for perfluoroalkyl sulfonic acid and its salt, and a compound that can substitute for perfluoroalkyl carboxylic acid and its salt, perfluoroalkyl sulfonic acid and its salt, and perfluoroalkyl carboxylic acid can be used.
- a coloring composition that is substantially free of salts thereof may be selected.
- Examples of compounds that can substitute for the regulated compound include compounds excluded from the regulation due to the difference in the number of carbon atoms of the perfluoroalkyl group. However, the above-mentioned contents do not prevent the use of perfluoroalkyl sulfonic acid and its salt, and perfluoroalkyl carboxylic acid and its salt.
- the coloring composition of the present invention may contain a perfluoroalkyl sulfonic acid and a salt thereof, and a perfluoroalkyl carboxylic acid and a salt thereof within the maximum allowable range.
- the coloring composition of the present invention does not substantially contain terephthalic acid ester.
- substantially free means that the content of the terephthalic acid ester is 1000 mass ppb or less in the total amount of the coloring composition, and more preferably 100 mass ppb or less. Zero is particularly preferred.
- the water content of the coloring composition of the present invention is usually 3% by mass or less, preferably 0.01 to 1.5% by mass, and more preferably 0.1 to 1.0% by mass.
- the water content can be measured by the Karl Fischer method.
- the coloring composition of the present invention can be used by adjusting the viscosity for the purpose of adjusting the film surface (flatness, etc.), adjusting the film thickness, and the like.
- the viscosity value can be appropriately selected as needed, but for example, at 25 ° C., 0.3 mPa ⁇ s to 50 mPa ⁇ s is preferable, and 0.5 mPa ⁇ s to 20 mPa ⁇ s is more preferable.
- a method for measuring the viscosity for example, a cone plate type viscometer can be used, and the viscosity can be measured in a state where the temperature is adjusted to 25 ° C.
- the container for containing the coloring composition is not particularly limited, and a known container can be used.
- a storage container for the purpose of suppressing impurities from being mixed into raw materials and coloring compositions, a multi-layer bottle having a container inner wall made of 6 types and 6 layers of resin and a bottle having 6 types of resin having a 7-layer structure. It is also preferable to use. Examples of such a container include the container described in JP-A-2015-123351.
- the inner wall of the container is preferably made of glass or stainless steel for the purpose of preventing metal elution from the inner wall of the container, enhancing the storage stability of the coloring composition, and suppressing the deterioration of the components.
- the coloring composition of the present invention can be prepared by mixing the above-mentioned components. In preparing the coloring composition, all the components may be dissolved and / or dispersed in a solvent at the same time to prepare the coloring composition, or each component may be appropriately used as two or more solutions or dispersions, if necessary. Then, these may be mixed at the time of use (at the time of application) to prepare a coloring composition.
- the mechanical force used for dispersing the pigment includes compression, squeezing, impact, shearing, cavitation and the like.
- Specific examples of these processes include bead mills, sand mills, roll mills, ball mills, paint shakers, microfluidizers, high speed impellers, sand grinders, flow jet mixers, high pressure wet atomization, ultrasonic dispersion and the like.
- the process and disperser for dispersing pigments are "Dispersion Technology Complete Works, Published by Information Organization Co., Ltd., July 15, 2005" and "Dispersion technology centered on suspension (solid / liquid dispersion system) and industrial”. Practical application The process and disperser described in Paragraph No.
- JP-A-2015-157893 "Comprehensive Data Collection, Published by Management Development Center Publishing Department, October 10, 1978" can be preferably used.
- the particles may be miniaturized in the salt milling step.
- the materials, equipment, processing conditions, and the like used in the salt milling step for example, the descriptions in JP-A-2015-194521 and JP-A-2012-046629 can be referred to.
- any filter that has been conventionally used for filtration or the like can be used without particular limitation.
- fluororesins such as polytetrafluoroethylene (PTFE) and polyvinylidene fluoride (PVDF)
- polyamide resins such as nylon (eg, nylon-6, nylon-6,6)
- polyolefin resins such as polyethylene and polypropylene (PP)
- PP polypropylene
- a filter using a material such as (including a high-density, ultra-high molecular weight polyethylene resin) and the like can be mentioned.
- polypropylene (including high-density polypropylene) and nylon are preferable.
- the pore diameter of the filter is preferably 0.01 to 7.0 ⁇ m, more preferably 0.01 to 3.0 ⁇ m, and even more preferably 0.05 to 0.5 ⁇ m. If the pore diameter of the filter is within the above range, fine foreign matter can be removed more reliably.
- the nominal value of the filter manufacturer can be referred to.
- various filters provided by Nippon Pole Co., Ltd. DFA4201NIEY, DFA4201NAEY, DFA4201J006P, etc.
- Advantech Toyo Co., Ltd., Nippon Entegris Co., Ltd. (formerly Nippon Microlith Co., Ltd.), Kitts Microfilter Co., Ltd., etc. can be used. ..
- a fiber-like filter medium As the filter.
- the fiber-like filter medium include polypropylene fiber, nylon fiber, glass fiber and the like.
- examples of commercially available products include SBP type series (SBP008, etc.), TPR type series (TPR002, TPR005, etc.) and SHPX type series (SHPX003, etc.) manufactured by Roki Techno Co., Ltd.
- filters different filters (eg, first filter and second filter, etc.) may be combined. At that time, the filtration with each filter may be performed only once or twice or more. Further, filters having different pore diameters may be combined within the above-mentioned range. Further, the filtration with the first filter may be performed only on the dispersion liquid, and after mixing the other components, the filtration may be performed with the second filter. Further, the filter can be appropriately selected according to the hydrophobicity of the coloring composition.
- the film of the present invention is a film obtained from the above-mentioned coloring composition of the present invention.
- the film of the present invention can be used for an optical filter such as a color filter or an infrared transmission filter.
- the film thickness of the film of the present invention can be appropriately adjusted according to the purpose.
- the film thickness is preferably 20 ⁇ m or less, more preferably 10 ⁇ m or less, and even more preferably 5 ⁇ m or less.
- the lower limit of the film thickness is preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more, still more preferably 0.3 ⁇ m or more.
- the film of the present invention When the film of the present invention is used as a color filter, the film of the present invention preferably has a hue of green, red, blue, cyan, magenta or yellow, and more preferably has a hue of green, red or yellow. preferable. Further, the film of the present invention can be preferably used as a colored pixel of a color filter. Examples of the colored pixels include red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, yellow pixels, and the like, preferably red pixels, green pixels, and yellow pixels, and are red pixels or green pixels. It is more preferable, and it is further preferable that it is a green pixel.
- the wavelength at which the light transmittance is 50% is preferably present in the wavelength range of 470 to 520 nm, more preferably in the wavelength range of 475 to 520 nm, and 480 to 520 nm. It is more preferred to be in the wavelength range. Above all, it is preferable that the wavelength at which the light transmittance is 50% exists in each of the wavelength range of 470 to 520 nm and the wavelength range of 575 to 625 nm. In this embodiment, the wavelength on the short wavelength side where the light transmittance is 50% preferably exists in the wavelength range of 475 to 520 nm, and more preferably exists in the wavelength range of 480 to 520 nm.
- the wavelength on the long wavelength side where the light transmittance is 50% preferably exists in the wavelength range of 580 to 620 nm, and more preferably exists in the wavelength range of 585 to 615 nm.
- a film having such spectral characteristics is preferably used as a green pixel.
- the film of the present invention preferably has, for example, any of the following spectral characteristics (1) to (4).
- the maximum value of the light transmittance in the film thickness direction in the wavelength range of 400 to 640 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the light transmittance in the film thickness direction.
- the minimum value of the rate in the wavelength range of 800 to 1300 nm is 70% or more (preferably 75% or more, more preferably 80% or more).
- a film having such spectral characteristics can block light in the wavelength range of 400 to 640 nm and transmit light having a wavelength of more than 700 nm.
- the maximum value of the light transmittance in the film thickness direction in the wavelength range of 400 to 750 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the light transmittance in the film thickness direction.
- a film having such spectral characteristics can block light in the wavelength range of 400 to 750 nm and transmit light having a wavelength of more than 850 nm.
- the maximum value of the light transmittance in the film thickness direction in the wavelength range of 400 to 830 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the light transmittance in the film thickness direction.
- a film having such spectral characteristics can block light in the wavelength range of 400 to 830 nm and transmit light having a wavelength exceeding 940 nm.
- the maximum value of the light transmittance in the film thickness direction in the wavelength range of 400 to 950 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the light transmittance in the film thickness direction.
- a film having such spectral characteristics can block light in the wavelength range of 400 to 950 nm and transmit light having a wavelength of more than 1040 nm.
- the film of the present invention can be produced through a step of applying the coloring composition of the present invention.
- the film manufacturing method preferably further includes a step of forming a pattern (pixel).
- Examples of the method for forming a pattern (pixel) include a photolithography method and a dry etching method. Since the coloring composition of the present invention has an excellent exposure latitude, the pattern is formed by the photolithography method. Especially excellent in.
- the pattern formation by the photolithography method includes a step of forming a colored composition layer on a support using the colored composition of the present invention, a step of exposing the colored composition layer in a pattern, and a step of exposing the colored composition layer into a pattern, and the coloring composition layer is not yet formed. It is preferable to include a step of developing and removing the exposed portion to form a pattern (pixel). If necessary, a step of baking the colored composition layer (pre-baking step) and a step of baking the developed pattern (pixels) (post-baking step) may be provided.
- the coloring composition layer of the present invention is used to form the coloring composition layer on the support.
- the support is not particularly limited and may be appropriately selected depending on the intended use. Examples thereof include a glass substrate and a silicon substrate, and a silicon substrate is preferable. Further, a charge-coupled device (CCD), a complementary metal oxide semiconductor (CMOS), a transparent conductive film, or the like may be formed on the silicon substrate. Further, a black matrix that separates each pixel may be formed on the silicon substrate. Further, the silicon substrate may be provided with a base layer for improving the adhesion with the upper layer, preventing the diffusion of substances, or flattening the surface of the substrate.
- the underlayer may be formed by using a composition obtained by removing a coloring agent from the coloring composition described in the present specification, a composition containing a curable compound, a surfactant and the like described in the present specification, and the like.
- the surface contact angle of the base layer is preferably 20 to 70 ° when measured with diiodomethane. Further, it is preferably 30 to 80 ° when measured with water. When the surface contact angle of the base layer is within the above range, the coating property of the coloring composition is good.
- the surface contact angle of the base layer can be adjusted by, for example, adding a surfactant.
- a known method can be used as a method for applying the coloring composition.
- a drop method drop cast
- a slit coat method for example, a spray method; a roll coat method; a rotary coating method (spin coating); a cast coating method; a slit and spin method; a pre-wet method (for example, JP-A-2009-145395).
- Methods described in the publication Inkjet (for example, on-demand method, piezo method, thermal method), ejection system printing such as nozzle jet, flexographic printing, screen printing, gravure printing, reverse offset printing, metal mask printing method, etc.
- Various printing methods; transfer method using a mold or the like; nanoinprint method and the like can be mentioned.
- the method of application in inkjet is not particularly limited, and is, for example, the method shown in "Expandable / usable inkjet-infinite possibilities seen in patents-, published in February 2005, Sumi Betechno Research" (especially from page 115). Page 133), JP-A-2003-262716, JP-A-2003-185831, JP-A-2003-261827, JP-A-2012-126830, JP-A-2006-169325, and the like. Can be mentioned. Further, regarding the method of applying the coloring composition, the description of International Publication No. 2017/030174 and International Publication No. 2017/018419 can be referred to, and these contents are incorporated in the present specification.
- the colored composition layer formed on the support may be dried (prebaked).
- prebaking may not be performed.
- the prebake temperature is preferably 150 ° C. or lower, more preferably 120 ° C. or lower, still more preferably 110 ° C. or lower.
- the lower limit can be, for example, 50 ° C. or higher, or 80 ° C. or higher.
- the prebake time is preferably 10 to 300 seconds, more preferably 40 to 250 seconds, still more preferably 80 to 220 seconds. Pre-baking can be performed on a hot plate, an oven, or the like.
- the colored composition layer is exposed in a pattern (exposure step).
- the colored composition layer can be exposed in a pattern by exposing the colored composition layer through a mask having a predetermined mask pattern using a stepper exposure machine, a scanner exposure machine, or the like. As a result, the exposed portion can be cured.
- Examples of radiation (light) that can be used for exposure include g-line and i-line. Further, light having a wavelength of 300 nm or less (preferably light having a wavelength of 180 to 300 nm) can also be used. Examples of the light having a wavelength of 300 nm or less include KrF line (wavelength 248 nm), ArF line (wavelength 193 nm) and the like, and KrF line (wavelength 248 nm) is preferable. Further, a long wave light source having a diameter of 300 nm or more can also be used.
- pulse exposure is an exposure method of a method in which light irradiation and pause are repeated in a cycle of a short time (for example, a millisecond level or less).
- Irradiation dose for example, preferably 0.03 ⁇ 2.5J / cm 2, more preferably 0.05 ⁇ 1.0J / cm 2.
- the oxygen concentration at the time of exposure can be appropriately selected, and in addition to the oxygen concentration performed in the atmosphere, for example, in a low oxygen atmosphere having an oxygen concentration of 19% by volume or less (for example, 15% by volume, 5% by volume, or substantially). It may be exposed in an oxygen-free environment (for example, 22% by volume, 30% by volume, or 50% by volume) in a high oxygen atmosphere having an oxygen concentration of more than 21% by volume.
- the exposure illuminance can be set as appropriate, and is usually selected from the range of 1000 W / m 2 to 100,000 W / m 2 (for example, 5000 W / m 2 , 15,000 W / m 2 , or 35,000 W / m 2). Can be done.
- the oxygen concentration and the exposure illuminance may be appropriately combined with each other.
- the oxygen concentration may be 10% by volume and the illuminance may be 10,000 W / m 2
- the oxygen concentration may be 35% by volume and the illuminance may be 20000 W / m 2 .
- the unexposed portion of the coloring composition layer is developed and removed to form a pattern (pixel).
- the development and removal of the unexposed portion of the coloring composition layer can be performed using a developing solution.
- the colored composition layer of the unexposed portion in the exposure step is eluted in the developing solution, and only the photocured portion remains.
- the temperature of the developer is preferably, for example, 20 to 30 ° C.
- the development time is preferably 20 to 180 seconds. Further, in order to improve the residue removability, the steps of shaking off the developer every 60 seconds and supplying a new developer may be repeated several times.
- Examples of the developing solution include organic solvents and alkaline developing solutions, and alkaline developing solutions are preferably used.
- the alkaline developer an alkaline aqueous solution (alkaline developer) obtained by diluting an alkaline agent with pure water is preferable.
- the alkaline agent include ammonia, ethylamine, diethylamine, dimethylethanolamine, diglycolamine, diethanolamine, hydroxyamine, ethylenediamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, and tetrabutylammonium hydroxide.
- Ethyltrimethylammonium hydroxide Ethyltrimethylammonium hydroxide, benzyltrimethylammonium hydroxide, dimethylbis (2-hydroxyethyl) ammonium hydroxide, choline, pyrrole, piperidine, 1,8-diazabicyclo- [5.4.0] -7-undecene, etc.
- examples thereof include organic alkaline compounds and inorganic alkaline compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogencarbonate, sodium silicate and sodium metasilicate.
- the alkaline agent a compound having a large molecular weight is preferable in terms of environment and safety.
- the concentration of the alkaline agent in the alkaline aqueous solution is preferably 0.001 to 10% by mass, more preferably 0.01 to 1% by mass.
- the developer may further contain a surfactant. From the viewpoint of convenience of transfer and storage, the developer may be once produced as a concentrated solution and diluted to a concentration required for use.
- the dilution ratio is not particularly limited, but can be set in the range of, for example, 1.5 to 100 times. It is also preferable to wash (rinse) with pure water after development. Further, it is preferable that the rinsing is performed by supplying the rinsing liquid to the developed colored composition layer while rotating the support on which the developed colored composition layer is formed.
- the nozzle for discharging the rinse liquid from the central portion of the support it is also preferable to move the nozzle for discharging the rinse liquid from the central portion of the support to the peripheral edge of the support.
- the nozzle may be moved while gradually reducing the moving speed. By rinsing in this way, in-plane variation of the rinse can be suppressed. Further, the same effect can be obtained by gradually reducing the rotation speed of the support while moving the nozzle from the central portion of the support to the peripheral portion.
- Additional exposure processing and post-baking are post-development curing treatments to complete the curing.
- the heating temperature in the post-bake is, for example, preferably 100 to 240 ° C, more preferably 200 to 240 ° C.
- Post-baking can be performed on the developed film in a continuous or batch manner using a heating means such as a hot plate, a convection oven (hot air circulation type dryer), or a high frequency heater so as to meet the above conditions. ..
- the light used for the exposure is preferably light having a wavelength of 400 nm or less. Further, the additional exposure process may be performed by the method described in Korean Patent Publication No. 10-2017-0122130.
- the pattern formation by the dry etching method includes a step of forming a colored composition layer on a support using the colored composition of the present invention and curing the entire colored composition layer to form a cured product layer.
- the optical filter of the present invention has the above-mentioned film of the present invention.
- Examples of the type of the optical filter include a color filter and an infrared transmission filter, and a color filter is preferable.
- As the color filter it is preferable to have the film of the present invention as the colored pixels of the color filter.
- the film thickness of the film of the present invention can be appropriately adjusted according to the purpose.
- the film thickness is preferably 5 ⁇ m or less, more preferably 1 ⁇ m or less, and even more preferably 0.6 ⁇ m or less.
- the lower limit of the film thickness is preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more, still more preferably 0.3 ⁇ m or more.
- the line width of the pixels included in the optical filter is preferably 0.4 to 10.0 ⁇ m.
- the lower limit is preferably 0.4 ⁇ m or more, more preferably 0.5 ⁇ m or more, and further preferably 0.6 ⁇ m or more.
- the upper limit is preferably 5.0 ⁇ m or less, more preferably 2.0 ⁇ m or less, further preferably 1.0 ⁇ m or less, further preferably 0.9 ⁇ m or less, and even more preferably 0.8 ⁇ m. The following is particularly preferable.
- the Young's modulus of the pixel is preferably 0.5 to 20 GPa, more preferably 2.5 to 15 GPa.
- each pixel included in the optical filter has high flatness.
- the surface roughness Ra of the pixel is preferably 100 nm or less, more preferably 40 nm or less, and further preferably 15 nm or less.
- the lower limit is not specified, but it is preferably 0.1 nm or more, for example.
- the surface roughness of the pixel can be measured using, for example, an AFM (atomic force microscope) Measurement 3100 manufactured by Veeco.
- the contact angle of water on the pixel can be appropriately set to a preferable value, but is typically in the range of 50 to 110 °.
- the contact angle can be measured using, for example, a contact angle meter CV-DT ⁇ A type (manufactured by Kyowa Interface Science Co., Ltd.). Further, it is preferable that the volume resistance value of the pixel is high. Specifically, it is preferred that the volume resistivity value of the pixel is 10 9 ⁇ ⁇ cm or more, and more preferably 10 11 ⁇ ⁇ cm or more. The upper limit is not specified, but it is preferably 10 14 ⁇ ⁇ cm or less, for example.
- the volume resistance value of the pixel can be measured using an ultra-high resistance meter 5410 (manufactured by Advantest).
- a protective layer may be provided on the surface of the film of the present invention.
- various functions such as oxygen blocking, low reflection, prohydrophobicization, and shielding of light of a specific wavelength (ultraviolet rays, near infrared rays, etc.) can be imparted.
- the thickness of the protective layer is preferably 0.01 to 10 ⁇ m, more preferably 0.1 to 5 ⁇ m.
- Examples of the method for forming the protective layer include a method of applying a resin composition dissolved in an organic solvent to form the protective layer, a chemical vapor deposition method, and a method of attaching a molded resin with an adhesive.
- the components constituting the protective layer include (meth) acrylic resin, en-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, and polyimide.
- Resin polyamideimide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, polyol resin, polyvinylidene chloride resin, melamine resin, urethane resin, aramid resin, polyamide resin, alkyd resin, epoxy resin, modified silicone resin, fluorine Examples thereof include resins, polycarbonate resins, polyacrylonitrile resins, cellulose resins, Si, C, W, Al 2 O 3 , Mo, SiO 2 , Si 2 N 4, and the like, and two or more of these components may be contained.
- the protective layer for the purpose of blocking oxygen, it is preferable that the protective layer contains a polyol resin, SiO 2 , and Si 2 N 4. Further, in the case of a protective layer for the purpose of reducing reflection, it is preferable that the protective layer contains a (meth) acrylic resin and a fluororesin.
- a known method such as a spin coating method, a casting method, a screen printing method, or an inkjet method can be used as the application method of the resin composition.
- a known organic solvent for example, propylene glycol 1-monomethyl ether 2-acetate, cyclopentanone, ethyl lactate, etc.
- the protective layer is formed by the chemical vapor deposition method
- the known chemical vapor deposition method thermochemical vapor deposition method, plasma chemical vapor deposition method, photochemical vapor deposition method
- the chemical vapor deposition method is used as the chemical vapor deposition method. Can be used.
- the protective layer may be an additive such as organic / inorganic fine particles, an absorber for light of a specific wavelength (for example, ultraviolet rays, near infrared rays, etc.), a refractive index adjusting agent, an antioxidant, an adhesive, and a surfactant, if necessary. May be contained.
- organic / inorganic fine particles include polymer fine particles (for example, silicone resin fine particles, polystyrene fine particles, melamine resin fine particles), titanium oxide, zinc oxide, zirconium oxide, indium oxide, aluminum oxide, titanium nitride, and titanium oxynitride. , Magnesium fluoride, hollow silica, silica, calcium carbonate, barium sulfate and the like.
- a known absorber can be used as the absorber of light having a specific wavelength.
- the content of these additives can be adjusted as appropriate, but is preferably 0.1 to 70% by mass, more preferably 1 to 60% by mass, based on the total mass of the protective layer.
- the protective layer the protective layer described in paragraphs 0073 to 0092 of JP-A-2017-151176 can also be used.
- the optical filter may have a structure in which each pixel is embedded in a space partitioned by a partition wall, for example, in a grid pattern.
- the solid-state image sensor of the present invention has the above-mentioned film of the present invention.
- the configuration of the solid-state image sensor is not particularly limited as long as it includes the film of the present invention and functions as a solid-state image sensor, and examples thereof include the following configurations.
- a transfer electrode formed of a plurality of photodiodes constituting a light receiving area of a solid-state image pickup device (CCD (charge-coupled device) image sensor, CMOS (complementary metal oxide semiconductor) image sensor, etc.) and polycarbonate on a substrate. It has a light-shielding film having only the light-receiving part of the photodiode open on the photodiode and the transfer electrode, and is formed of silicon nitride or the like formed on the light-shielding film so as to cover the entire surface of the light-shielding film and the light-receiving part of the photodiode. It has a device protective film and a color filter on the device protective film.
- CCD charge-coupled device
- CMOS complementary metal oxide semiconductor
- the color filter may have a structure in which each colored pixel is embedded in a space partitioned by a partition wall, for example, in a grid pattern.
- the partition wall preferably has a low refractive index for each colored pixel. Examples of the image pickup apparatus having such a structure include the apparatus described in JP-A-2012-227478, JP-A-2014-179757, and International Publication No. 2018/043654.
- an ultraviolet absorbing layer may be provided in the structure of the solid-state image sensor to improve the light resistance.
- the image pickup device provided with the solid-state image pickup device of the present invention can be used not only for digital cameras and electronic devices having an image pickup function (mobile phones and the like), but also for in-vehicle cameras and surveillance cameras.
- the image display device of the present invention has the above-mentioned film of the present invention.
- the image display device include a liquid crystal display device and an organic electroluminescence display device.
- the liquid crystal display device is described in, for example, “Next Generation Liquid Crystal Display Technology (edited by Tatsuo Uchida, Kogyo Chosakai Co., Ltd., published in 1994)”.
- the liquid crystal display device to which the present invention can be applied is not particularly limited, and can be applied to, for example, various types of liquid crystal display devices described in the above-mentioned "next-generation liquid crystal display technology".
- Compounds (a-1) to (a-11) and compounds (b-1) to (b-7) are compounds having the following structures, respectively.
- the metal salt (m-1) is zinc acetate
- the metal salt (m-2) is copper acetate
- the metal salt (m-3) is iron acetate
- the hydrochloride salt (c-1) is pyridine. It is a hydrochloride
- the hydrochloride (c-2) is an imidazole hydrochloride
- the hydrochloride (c-3) is a trimethylamine hydrochloride.
- Synthesis Example 20 Synthesis of compound (S-20) The same operation as in Synthesis Example 19 was carried out except that the compound (S-1) of the synthesis example 19 was changed to the compound (S-4), and the compound (S-20) was performed. ) was obtained. In the gas chromatography measurement of compound (S-20), it was confirmed that the peak of pyridine corresponding to the pyridinium ion disappeared.
- PY117 C.I. I. Pigment Yellow 117 (azomethine copper complex, yellow pigment)
- PY129 C.I. I. Pigment Yellow 129 (azomethine copper complex, yellow pigment)
- PY138 C.I. I. Pigment Yellow 138 (quinophthalone compound, yellow pigment)
- PY139 C.I. I. Pigment Yellow 139 (isoindoline compound, yellow pigment)
- PY150 C.I. I. Pigment Yellow 150 (azonickel complex, yellow pigment)
- PY185 C.I. I.
- Pigment Yellow 185 (isoindoline compound, yellow pigment)
- Y-1 Compounds with the following structure (quinophthalone compounds, yellow pigments)
- Y-2 Compounds with the following structure (quinophthalone compounds, yellow pigments)
- Y-3 Compound with the following structure (azomethine zinc complex, yellow pigment)
- PG7 C.I. I. Pigment Green 7 (copper phthalocyanine complex, green pigment)
- PG36 C.I. I. Pigment Green 36 (copper phthalocyanine complex, green pigment)
- PG58 C.I. I. Pigment Green 58 (zinc phthalocyanine complex, green pigment)
- PG59 C.I. I.
- Pigment Green 59 (zinc phthalocyanine complex, green pigment)
- PG62 C.I. I. Pigment Green 62 (aluminum phthalocyanine complex, green pigment)
- PG63 C.I. I. Pigment Green 63 (aluminum phthalocyanine complex, green pigment)
- PR254 C.I. I. Pigment Red 254 (diketopyrrolopyrrole compound, red pigment)
- PR264 C.I. I. Pigment Red 264 (diketopyrrolopyrrole compound, red pigment)
- PR272 C.I. I. Pigment Red 272 (diketopyrrolopyrrole compound, red pigment)
- PR122 C.I. I. Pigment Red 122 (quinacridone compound, red pigment)
- (Dispersant) B-1 Resin having the following structure (graft resin having a polyester structure graft chain, the numerical value added to the main chain is the molar ratio, and the numerical value added to the side chain is the number of repeating units. Weight average molecular weight 24000, Acid value 47mgKOH / g)
- B-2 Resin having the following structure (graft resin having a polyester structure graft chain, the numerical value added to the main chain is the molar ratio, and the numerical value added to the side chain is the number of repeating units.
- B-3 Resin having the following structure (graft resin having a graft chain having a poly (meth) acrylic structure, the numerical value added to the main chain is the mass ratio, and the numerical value added to the side chain is the number of repeating units. Average molecular weight 13000, acid value 65 mgKOH / g)
- Resin B-4 synthesized by the following method 50 parts by mass of methyl methacrylate, 30 parts by mass of n-butyl methacrylate, 20 parts by mass of t-butyl methacrylate, and 45.4 parts by mass of PGMEA (propylene glycol monomethyl ether acetate) were charged in a reaction vessel, and the atmosphere gas was replaced with nitrogen gas. The inside of the reaction vessel is heated to 70 ° C., 6 parts by mass of 3-mercapto-1,2-propanediol is added, and 0.12 parts by mass of AIBN (azobisisobutyronitrile) is further added, and the reaction is carried out for 12 hours. I let you. It was confirmed by solid content measurement that 95% had reacted.
- AIBN azobisisobutyronitrile
- B-12 Resin having the following structure (resin in which the end of a polymer chain having a poly (meth) acrylic structure is sealed with an acid group, weight average molecular weight 3,200, acid value 27 mgKOH / g)
- B-13 Resin having the following structure (resin in which the end of a polymer chain having a poly (meth) acrylic structure is sealed with an acid group, weight average molecular weight 3500, acid value 77 mgKOH / g)
- BH-1 Polyamic acid having the following structure (the numerical value added to the repeating unit is the molar ratio. Weight average molecular weight 20000)
- S-1 to S-20 The above-mentioned compounds (S-1) to (S-20) SD-1: Compound with the following structure SD-2: Compound with the following structure SH-1: Compound with the following structure (Compound synthesized by the synthetic method described in paragraph No. 0073 of JP-A-2009-035671)
- Surfactant 1 A 1% by mass PGMEA solution of a compound having the following structure (weight average molecular weight 14000, numerical value indicating the ratio of repeating units is mol%).
- (resin) b1 Resin having the following structure (the numerical value added to the main chain is the molar ratio. Weight average molecular weight 30,000) b2: Resin having the following structure (the numerical value added to the main chain is the molar ratio. Weight average molecular weight 11000) b3: Resin having the structure described in the above-mentioned dispersant b3.
- a transparent substrate (CT-4000L, manufactured by FUJIFILM Electronics Materials Co., Ltd.) is applied on a silicon wafer with a diameter of 8 inches (20.32 cm) so that the dry film thickness is 0.1 ⁇ m, and the wafer is dried.
- heat treatment was performed at 220 ° C. for 5 minutes to obtain a silicon wafer with a base layer.
- each of the colored compositions of Examples and Comparative Examples prepared as described above was applied onto the base layer of the silicon wafer with a base layer to form a colored composition layer (coating film). Then, heat treatment (pre-baking) was performed for 120 seconds using a hot plate at 100 ° C.
- the dry film thickness of the coating film was 0.5 ⁇ m.
- an i-line stepper exposure device FPA-3000i5 + manufactured by Canon Inc.
- light having a wavelength of 365 nm was exposed through a 0.9 ⁇ m square Island pattern mask at various exposure amounts of 50 to 1200 mJ / cm 2. ..
- the silicon wafer on which the irradiated coating film was formed was placed on a horizontal rotary table of a spin shower developer (DW-30 type, manufactured by Chemitronics Co., Ltd.), and a developer (CD-2000, Paddle development was performed at 23 ° C. for 60 seconds using Fujifilm Electronics Materials Co., Ltd.
- DW-30 type manufactured by Chemitronics Co., Ltd.
- the silicon wafer on which the film after paddle development is formed is fixed to a horizontal rotary table by a vacuum chuck method, and while the silicon wafer is rotated at a rotation speed of 50 rpm by a rotating device, pure water is applied from above the rotation center. It was supplied in the form of a shower from a ejection nozzle, rinsed, and then spray-dried. Then, heat treatment (post-baking) was performed at 200 ° C. for 300 seconds using a hot plate to form colored pixels. As described above, a monochromatic color filter having colored pixels formed by the colored composition of the example or the comparative example was produced.
- the line width of the colored pixel was measured using a length measuring SEM "S-9260A” (manufactured by Hitachi High-Technologies Corporation).
- the optimum exposure amount was defined as the exposure amount at which the line width of the colored pixels was 1.2 ⁇ m.
- the colored compositions of Examples 13, 22 and 29 were spin-coated on a glass substrate and prebaked at 90 ° C. for 120 seconds to obtain a coating film having a film thickness of 2.0 ⁇ m.
- a cured film was prepared by irradiating with a high-pressure mercury lamp at an exposure amount of 500 mJ / cm 2 (i-line equivalent) and further baking at 120 ° C. for 60 minutes in an oven.
- the obtained cured film was rubbed 10 times with steel wool # 0000 and a load of 500 g, and was visually evaluated. As a result, no scratches were observed and the scratch resistance was excellent.
- Example 73 For the coloring composition of Example 73, colored pixels having a finer line width were formed using a 0.8 ⁇ m square Island pattern mask, and the exposure latitude and the developer resistance were evaluated. It was found that there were good results.
- Example 101 In the coloring composition of Example 1, the coloring composition of Example 101 was prepared in the same manner as in Example 1 except that the photopolymerization initiator I-1 was changed to a thermal polymerization initiator (tert-butylperoxybenzoate). Manufactured.
- Example 101 The coloring composition of Example 101 was applied onto a glass wafer with a spin coater so as to form a coating film having a film thickness of 0.6 ⁇ m, dried at 100 ° C. for 180 seconds using a hot plate, and then dried at 200 ° C. for 300 ° C. Heat treatment (post-baking) was performed for seconds to form a colored layer. The film thickness of this colored layer was 0.6 ⁇ m. Next, a positive photoresist (FHi622BC, manufactured by FUJIFILM Electronics Materials) was applied onto the colored layer and prebaked to form a photoresist layer having a film thickness of 0.8 ⁇ m.
- FHi622BC manufactured by FUJIFILM Electronics Materials
- the photoresist layer was pattern-exposed with an i-line stepper (manufactured by Canon Inc.) at an exposure amount of 350 mJ / cm 2 , and the temperature of the photoresist layer or the ambient temperature was 90 ° C. for 1 minute. Heat treatment was performed. Then, a developing solution (FHD-5, manufactured by FUJIFILM Electronics Materials Co., Ltd.) was used for 1 minute of development treatment, and then a post-baking treatment at 110 ° C. for 1 minute was carried out to form a resist pattern.
- an i-line stepper manufactured by Canon Inc.
- a developing solution FHD-5, manufactured by FUJIFILM Electronics Materials Co., Ltd.
- This resist pattern is a pattern in which square resist films formed with a side of 0.9 ⁇ m are arranged in a checkered pattern in consideration of the etching conversion difference (reduction of the pattern width due to etching).
- dry etching of the colored layer was performed by the following procedure.
- a photoresist stripping solution (MS230C, manufactured by Fujifilm Electronics Materials Co., Ltd.) was used to perform stripping treatment for 120 seconds to remove the resist pattern, and then cleaning with pure water. Spin drying was performed. Then, a dehydration bake treatment was performed at 100 ° C. for 2 minutes. As a result, a colored pattern in which square-shaped colored pixels having a side of 0.9 ⁇ m (colored pixels having a line width of 0.9 ⁇ m) are arranged in a checkered pattern was obtained.
- the silicon wafer on which the coloring pattern was formed was placed on a horizontal rotary table of a spin shower developer (DW-30 type, manufactured by Chemitronics Co., Ltd.), and a developer (CD-2000, FUJIFILM Electronics Materials) ( (Co., Ltd.) was used to perform paddle development at 23 ° C. for 60 seconds, and the development process was carried out.
- the silicon wafer substrate was fixed to a horizontal rotary table by a vacuum chuck method, and the silicon wafer substrate was rotated at a rotation speed of 50 rpm by a rotary device. Pure water was supplied from above the center of rotation in a shower shape from above the center of rotation to perform a rinsing treatment, and then spray-dried.
- Example 1001 The green coloring composition was applied onto the silicon wafer by a spin coating method so that the film thickness after film formation was 1.0 ⁇ m. Then, using a hot plate, it was heated at 100 ° C. for 2 minutes. Next, using an i-line stepper exposure apparatus FPA-3000i5 + (manufactured by Canon Inc.) , exposure was performed with an exposure amount of 1000 mJ / cm 2 via a mask of a 2 ⁇ m square dot pattern. Then, paddle development was performed at 23 ° C. for 60 seconds using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide (TMAH). Then, it was rinsed with a spin shower and then washed with pure water.
- TMAH tetramethylammonium hydroxide
- the green coloring composition was patterned to form green pixels by heating at 200 ° C. for 5 minutes using a hot plate.
- the red coloring composition and the blue coloring composition were patterned by the same process to sequentially form red pixels and blue pixels to form a color filter having green pixels, red pixels and blue pixels.
- green pixels are formed by a Bayer pattern
- red pixels and blue pixels are formed by an island pattern in an adjacent region thereof.
- the obtained color filter was incorporated into a solid-state image sensor according to a known method. This solid-state image sensor had suitable image recognition ability.
- the green coloring composition the coloring composition of Example 50 was used.
- the red coloring composition the coloring composition of Example 53 was used.
- the blue coloring composition the one produced by the following method was used.
- the raw materials used to prepare the blue coloring composition are as follows.
- a high-pressure disperser with a decompression mechanism NANO-3000-10 manufactured by Nippon BEE Co., Ltd. was used to perform a dispersion treatment under a pressure of 2000 kg / cm 3 at a flow rate of 500 g / min. This dispersion treatment was repeated 10 times to obtain a blue pigment dispersion liquid.
- Polymerizable compound 101 KAYARAD DPHA (manufactured by Nippon Kayaku Co., Ltd.)
- Polymerizable compound 102 A compound having the following structure
- Photopolymerization initiator 101 Irgacure OXE01 (manufactured by BASF)
- Example 1002 A cyan-colored composition was applied onto a silicon wafer by a spin coating method so that the film thickness after film formation was 1.0 ⁇ m. Then, using a hot plate, it was heated at 100 ° C. for 2 minutes. Next, using an i-line stepper exposure apparatus FPA-3000i5 + (manufactured by Canon Inc.) , exposure was performed with an exposure amount of 1000 mJ / cm 2 via a mask of a 2 ⁇ m square dot pattern. Then, paddle development was performed at 23 ° C. for 60 seconds using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide (TMAH). Then, it was rinsed with a spin shower and then washed with pure water.
- TMAH tetramethylammonium hydroxide
- the cyan-colored composition was patterned to form cyan-colored pixels.
- the yellow coloring composition and the magenta coloring composition were patterned by the same process to sequentially form yellow pixels and magenta color pixels to form a color filter having cyan color pixels, yellow pixels and magenta color pixels. ..
- cyan pixels are formed by a Bayer pattern, and yellow pixels and magenta pixels are formed by an island pattern in an adjacent region thereof.
- the obtained color filter was incorporated into a solid-state image sensor according to a known method. This solid-state image sensor had suitable image recognition ability.
- the yellow coloring composition uses the coloring composition of Example 1, the cyan coloring composition uses the coloring composition of Example 40, and the magenta coloring composition uses the coloring composition of Example 49. I used a thing.
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Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202180045956.1A CN115996991B (zh) | 2020-07-08 | 2021-05-18 | 着色组合物、膜、滤光器、固体摄像元件、图像显示装置及化合物 |
| JP2022534927A JP7496873B2 (ja) | 2020-07-08 | 2021-05-18 | 着色組成物、膜、光学フィルタ、固体撮像素子、画像表示装置及び化合物 |
| KR1020227045880A KR102746098B1 (ko) | 2020-07-08 | 2021-05-18 | 착색 조성물, 막, 광학 필터, 고체 촬상 소자, 화상 표시 장치 및 화합물 |
| US18/069,364 US12529969B2 (en) | 2020-07-08 | 2022-12-21 | Coloring composition, film, optical filter, solid-state imaging element, image display device, and compound |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022168742A1 (ja) * | 2021-02-03 | 2022-08-11 | 富士フイルム株式会社 | 着色組成物、膜、光学フィルタ、固体撮像素子、画像表示装置および化合物 |
| WO2022168741A1 (ja) * | 2021-02-03 | 2022-08-11 | 富士フイルム株式会社 | 着色組成物、膜、光学フィルタ、固体撮像素子、画像表示装置および化合物 |
| WO2023181855A1 (ja) * | 2022-03-23 | 2023-09-28 | 三菱ケミカル株式会社 | 感光性組成物及びパターン形成方法 |
| WO2024018910A1 (ja) * | 2022-07-19 | 2024-01-25 | 富士フイルム株式会社 | 着色組成物、膜、光学フィルタ、固体撮像素子、画像表示装置および着色剤 |
| WO2026063235A1 (ja) * | 2024-09-18 | 2026-03-26 | 株式会社日本触媒 | 樹脂組成物 |
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| WO2020022248A1 (ja) * | 2018-07-26 | 2020-01-30 | 富士フイルム株式会社 | 硬化性組成物、膜、カラーフィルタ、カラーフィルタの製造方法、固体撮像素子および画像表示装置 |
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| JP2025144930A (ja) | 2024-03-21 | 2025-10-03 | 愛三工業株式会社 | 固定構造 |
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- 2021-05-18 CN CN202180045956.1A patent/CN115996991B/zh active Active
- 2021-05-18 JP JP2022534927A patent/JP7496873B2/ja active Active
- 2021-05-18 KR KR1020227045880A patent/KR102746098B1/ko active Active
- 2021-05-21 TW TW110118355A patent/TWI890791B/zh active
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| WO2022168742A1 (ja) * | 2021-02-03 | 2022-08-11 | 富士フイルム株式会社 | 着色組成物、膜、光学フィルタ、固体撮像素子、画像表示装置および化合物 |
| WO2022168741A1 (ja) * | 2021-02-03 | 2022-08-11 | 富士フイルム株式会社 | 着色組成物、膜、光学フィルタ、固体撮像素子、画像表示装置および化合物 |
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| WO2026063235A1 (ja) * | 2024-09-18 | 2026-03-26 | 株式会社日本触媒 | 樹脂組成物 |
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| US20230126240A1 (en) | 2023-04-27 |
| TWI890791B (zh) | 2025-07-21 |
| CN115996991A (zh) | 2023-04-21 |
| TW202216913A (zh) | 2022-05-01 |
| US12529969B2 (en) | 2026-01-20 |
| CN115996991B (zh) | 2024-12-31 |
| KR102746098B1 (ko) | 2024-12-26 |
| JPWO2022009526A1 (https=) | 2022-01-13 |
| JP7496873B2 (ja) | 2024-06-07 |
| KR20230017277A (ko) | 2023-02-03 |
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