WO2022181158A1 - 着色組成物、膜、カラーフィルタおよび固体撮像素子 - Google Patents
着色組成物、膜、カラーフィルタおよび固体撮像素子 Download PDFInfo
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- WO2022181158A1 WO2022181158A1 PCT/JP2022/002606 JP2022002606W WO2022181158A1 WO 2022181158 A1 WO2022181158 A1 WO 2022181158A1 JP 2022002606 W JP2022002606 W JP 2022002606W WO 2022181158 A1 WO2022181158 A1 WO 2022181158A1
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- KVFVBPYVNUCWJX-UHFFFAOYSA-M ethyl(trimethyl)azanium;hydroxide Chemical compound [OH-].CC[N+](C)(C)C KVFVBPYVNUCWJX-UHFFFAOYSA-M 0.000 description 1
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- 229910021645 metal ion Inorganic materials 0.000 description 1
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- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- UJRDRFZCRQNLJM-UHFFFAOYSA-N methyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OC)=CC(N2N=C3C=CC=CC3=N2)=C1O UJRDRFZCRQNLJM-UHFFFAOYSA-N 0.000 description 1
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- INJVFBCDVXYHGQ-UHFFFAOYSA-N n'-(3-triethoxysilylpropyl)ethane-1,2-diamine Chemical compound CCO[Si](OCC)(OCC)CCCNCCN INJVFBCDVXYHGQ-UHFFFAOYSA-N 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
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- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
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- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
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- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
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- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- HTSABYAWKQAHBT-UHFFFAOYSA-N trans 3-methylcyclohexanol Natural products CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 description 1
- OVTCUIZCVUGJHS-VQHVLOKHSA-N trans-dipyrrin Chemical compound C=1C=CNC=1/C=C1\C=CC=N1 OVTCUIZCVUGJHS-VQHVLOKHSA-N 0.000 description 1
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- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
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- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- ORHBXUUXSCNDEV-UHFFFAOYSA-N umbelliferone Chemical compound C1=CC(=O)OC2=CC(O)=CC=C21 ORHBXUUXSCNDEV-UHFFFAOYSA-N 0.000 description 1
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- 238000007740 vapor deposition Methods 0.000 description 1
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Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
- C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
-
- 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
- C08K5/0091—Complexes with metal-heteroatom-bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/0075—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of an heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
- C09B47/10—Obtaining compounds having halogen atoms directly bound to the phthalocyanine skeleton
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0034—Mixtures of two or more pigments or dyes of the same type
- C09B67/0035—Mixtures of phthalocyanines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/006—Preparation of organic pigments
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
- C09B67/0085—Non common dispersing agents
- C09B67/009—Non common dispersing agents polymeric dispersing agent
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- C09B67/0097—Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/20—Diluents or solvents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/41—Organic pigments; Organic dyes
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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
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- 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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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—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
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
- Y10S430/111—Polymer of unsaturated acid or ester
Definitions
- the present invention relates to a coloring composition containing a coloring agent.
- the present invention also relates to a film, a color filter and a solid-state imaging device using the coloring composition.
- CCD charge-coupled device
- Patent Document 1 discloses a phthalocyanine blue pigment containing either or both of Color Index Pigment Blue 15:3 and Color Index Pigment Blue 15:4, a phthalocyanine green pigment containing Color Index Pigment Green 7, and a resin. , a cyan coloring composition for color filters containing a polymerizable compound and a photopolymerization initiator.
- the composition layer formed by applying the coloring composition on a support When forming pixels by photolithography using a coloring composition containing a coloring agent, a polymerizable compound and a photopolymerization initiator, the composition layer formed by applying the coloring composition on a support , exposed through a mask having a pattern, and developing and removing the unexposed portions to form pixels.
- pixels may be formed using a coloring composition that has been stored for a long period of time at a low temperature. If the sensitivity of the coloring composition decreases during storage, even if pixels are formed under the same exposure conditions as the coloring composition before storage, the line width of the obtained pixels tends to differ. For this reason, it is desired that the coloring composition is excellent in stability of sensitivity over time.
- an object of the present invention is to provide a coloring composition in which the line width of the obtained pixel has a small illuminance dependence and excellent sensitivity stability over time.
- Another object of the present invention is to provide a film, a color filter and a solid-state imaging device.
- the present invention provides the following.
- a coloring composition containing a coloring agent, a resin, a polymerizable compound, a photopolymerization initiator, an ultraviolet absorber, and a solvent
- the colorant includes an unsubstituted copper phthalocyanine pigment and a halogenated copper phthalocyanine pigment
- a coloring composition wherein the content of the unsubstituted copper phthalocyanine pigment is 10% by mass or more and the content of the halogenated copper phthalocyanine pigment is 40% by mass or more in the total mass of the colorant.
- the unsubstituted copper phthalocyanine pigment contains Color Index Pigment Blue 15:4, The coloring composition according to ⁇ 1>, wherein the halogenated copper phthalocyanine pigment contains Color Index Pigment Green 7.
- the composition according to ⁇ 1> or ⁇ 2>, wherein the total content of the unsubstituted copper phthalocyanine pigment and the halogenated copper phthalocyanine pigment in the total weight of the colorant is 70 to 100% by mass.
- coloring composition. ⁇ 4> When a film having a thickness of 0.6 ⁇ m is formed using the coloring composition, the average transmittance of light in the wavelength range of 400 to 450 nm in the thickness direction of the film is 75% or more.
- the average value of the transmittance of light in the wavelength range of 650 to 700 nm in the thickness direction of the film is 30% or less, and the wavelength exhibiting the transmittance of 50% exists in the wavelength range of 560 to 590 nm, ⁇ 1>
- a coloring composition containing a coloring agent, a resin, a polymerizable compound, a photopolymerization initiator, an ultraviolet absorber, and a solvent,
- the average value of the transmittance of light in the wavelength range of 400 to 450 nm in the thickness direction of the film is 75% or more
- the film The average value of the transmittance of light in the wavelength range of 650 to 700 nm in the thickness direction is 30% or less, and the wavelength at which the transmittance is 50% is present in the wavelength range of 560 to 590 nm.
- ⁇ 6> The colored composition according to any one of ⁇ 1> to ⁇ 5>, wherein the content of the ultraviolet absorber in the total solid content of the colored composition is 0.5% by mass or more.
- ⁇ 7> The coloring according to any one of ⁇ 1> to ⁇ 6>, wherein the ultraviolet absorber has a ratio of absorbance A2 at a wavelength of 410 nm to absorbance A1 at a wavelength of 365 nm of 0.06 or less.
- Composition. ⁇ 8> The colored composition according to any one of ⁇ 1> to ⁇ 7>, wherein the ultraviolet absorber is at least one selected from conjugated diene compounds, benzotriazole compounds, dibenzoyl compounds and triazine compounds.
- the colored composition according to any one of ⁇ 1> to ⁇ 8> containing 100 to 350 parts by mass of the resin with respect to 100 parts by mass of the colorant.
- the resin includes a resin having at least one repeating unit selected from repeating units represented by formula (1) and repeating units represented by formula (2), ⁇ 1> to ⁇ 9>
- ⁇ 11> The content of Color Index Pigment Blue 15:4 in the total mass of the coloring agent is 10 to 50% by mass, The content of the photopolymerization initiator in the total solid content of the coloring composition is 3 to 10% by mass, The coloring composition according to any one of ⁇ 1> to ⁇ 10>, wherein the content of the ultraviolet absorber in the total solid content of the coloring composition is 1 to 10% by mass.
- ⁇ 12> A film obtained from the colored composition according to any one of ⁇ 1> to ⁇ 11>.
- ⁇ 13> A color filter having the film according to ⁇ 12>.
- ⁇ 14> A solid-state imaging device having the film according to ⁇ 12>.
- the present invention it is possible to provide a coloring composition in which the line width of the resulting pixel has a small illuminance dependence and excellent sensitivity stability over time. Moreover, the present invention can provide a film, a color filter, and a solid-state imaging device using the coloring composition.
- ⁇ is used to include the numerical values before and after it as lower and upper limits.
- a description that does not describe substitution or unsubstituted includes a group (atomic group) having no substituent as well as a group (atomic group) having a substituent.
- an "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).
- exposure includes not only exposure using light but also drawing using particle beams such as electron beams and ion beams, unless otherwise specified.
- Light used for exposure includes actinic rays or radiation such as emission line spectra of mercury lamps, far ultraviolet rays represented by excimer lasers, extreme ultraviolet rays (EUV light), X-rays, and electron beams.
- EUV light extreme ultraviolet rays
- (meth)acrylate” represents both or either acrylate and methacrylate
- (meth)acryl represents both or either acrylic and methacrylic
- (meth) ) acryloyl refers to acryloyl and/or methacryloyl.
- Me in the structural formulas 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 number average molecular weight are polystyrene equivalent values measured by GPC (gel permeation chromatography).
- total solid content refers to the total mass of all components of the composition excluding the solvent.
- a pigment means a coloring agent that is difficult to dissolve in a solvent.
- the term "process” includes not only an independent process, but also when the intended action of the process is achieved even if it cannot be clearly distinguished from other processes. .
- a first aspect of the coloring composition of the present invention is a coloring composition containing a coloring agent, a resin, a polymerizable compound, a photopolymerization initiator, an ultraviolet absorber and a solvent, wherein the coloring agent contains an unsubstituted copper phthalocyanine pigment and a halogenated copper phthalocyanine pigment, the content of the unsubstituted copper phthalocyanine pigment in the total weight of the coloring agent is 10% by mass or more, and the halogenated copper phthalocyanine pigment The content is 40% by mass or more.
- the coloring composition of the first aspect has an average transmittance of 75 for light in the wavelength range of 400 to 450 nm in the thickness direction of the film when a film having a thickness of 0.6 ⁇ m is formed from the coloring composition. % or more, the average transmittance of light in the wavelength range of 650 to 700 nm in the thickness direction of the film is 30% or less, and the wavelength at which the transmittance is 50% exists in the wavelength range of 560 to 590 nm. is preferred.
- a second aspect of the coloring composition of the present invention is a coloring composition containing a coloring agent, a resin, a polymerizable compound, a photopolymerization initiator, an ultraviolet absorber and a solvent, wherein the coloring
- the average value of the transmittance of light in the wavelength range of 400 to 450 nm in the thickness direction of the film is 75% or more.
- the average transmittance of light in the wavelength range of 650 to 700 nm is 30% or less, and the wavelength exhibiting the transmittance of 50% exists in the wavelength range of 560 to 590 nm.
- the coloring composition of the first aspect and the coloring composition of the second aspect are collectively referred to as the coloring composition of the present invention.
- the coloring composition of the present invention when pixels are formed by photolithography using the coloring composition, the line width of the obtained pixels has a small illuminance dependence, so that the illuminance conditions during exposure are varied. It is also possible to suppress variations in the line width of the obtained pixels.
- the coloring composition of the present invention is excellent in stability of sensitivity over time, and even when pixels are formed using the coloring composition after storage, variations in line width can be suppressed.
- the average transmittance of light in the wavelength range of 400 to 450 nm in the thickness direction of the film is 80% or more. Preferably, it is 85% or more.
- the average value of the transmittance of light in the wavelength range of 650 to 700 nm in the thickness direction of the film is 25% or less. preferably 20% or less.
- the wavelength at which the transmittance is 50% is preferably in the wavelength range of 565 to 585 nm, preferably 570 to 580 nm. More preferably in the range of A coloring composition having such spectral properties is preferably used as a coloring composition for forming cyan pixels.
- the coloring composition of the present invention is preferably used as a coloring composition for forming color filters. More specifically, it can be preferably used as a coloring composition for forming pixels of a color filter, and more preferably used as a coloring composition for forming cyan pixels of a color filter. Moreover, the coloring composition of the present invention is preferably used as a coloring composition for forming a color filter used in a solid-state imaging device. Each component used in the coloring composition of the present invention is described below.
- the coloring composition of the present invention contains a coloring agent.
- the coloring agent contained in the coloring composition of the present invention preferably contains an unsubstituted copper phthalocyanine pigment and a halogenated copper phthalocyanine pigment.
- a copper phthalocyanine pigment is a phthalocyanine pigment having a copper atom as a central metal. That is, a copper phthalocyanine pigment is a pigment having a structure in which a copper atom, which is a central metal, is coordinated with a phthalocyanine compound, which is a ligand.
- An unsubstituted copper phthalocyanine pigment is a pigment in which the phthalocyanine compound as a ligand is an unsubstituted phthalocyanine compound, that is, phthalocyanine.
- a halogenated copper phthalocyanine pigment is a pigment having a structure in which a phthalocyanine compound as a ligand is a phthalocyanine compound having a halogen atom as a substituent.
- Examples of unsubstituted copper phthalocyanine pigments include compounds represented by the following formula (Pc-1). Further, examples of halogenated copper phthalocyanine pigments include compounds represented by the following formula (Pc-2).
- X 1 to X 16 each represent a hydrogen atom or a halogen atom, and at least one of X 1 to X 16 represents a halogen atom.
- Halogen atoms represented by X 1 to X 16 include fluorine, chlorine, bromine and iodine atoms, preferably chlorine and bromine atoms.
- 4 to 16 of X 1 to X 16 are preferably halogen atoms, more preferably 8 to 16 are halogen atoms, still more preferably 12 to 16 are halogen atoms, and X 1 to X 16 are halogen atoms. It is particularly preferred that all of X 16 are halogen atoms.
- unsubstituted copper phthalocyanine pigments include Color Index (C.I.) Pigment Blue 15, 15:1, 15:2, 15:3, 15:4 and 15:6.
- the unsubstituted copper phthalocyanine pigment is C.I. I.
- Pigment Blue 15:4 is preferred. Only one kind of unsubstituted copper phthalocyanine pigment may be used, or two or more kinds thereof may be used in combination.
- the content of Pigment Blue 15:4 is preferably 90 to 100% by mass, more preferably 95 to 100% by mass, even more preferably 99 to 100% by mass.
- An unsubstituted copper phthalocyanine pigment is C.I. I. Especially preferred is Pigment Blue 15:4 only.
- halogenated copper phthalocyanine pigments include C.I. I. Pigment Green 7, 36 and the like.
- the copper phthalocyanine halide pigment is C.I. I. Pigment Green 7 is preferably included.
- Halogenated copper phthalocyanine pigments may be used alone or in combination of two or more.
- Preferred embodiments of the halogenated copper phthalocyanine pigment include the following embodiments 1 and 2. In the case of Mode 1, pixels having better spectral characteristics can be formed. In the case of aspect 2, the light resistance of the resulting film can be further improved.
- Aspect 1 Halogenated copper phthalocyanine pigment is C.I. I. Pigment Green 7 only
- Aspect 2 Halogenated copper phthalocyanine pigment is C.I. I. Pigment Green 7 and C.I. I. Pigment Green 36
- C.I. I. Pigment Green 7 and C.I. I. Pigment Green 36 and C.I. I. C.I. to 100 parts by mass of Pigment Green 7 I. Pigment Green 36 is preferably 10 to 50 parts by mass.
- the upper limit is preferably 45 parts by mass or less, more preferably 40 parts by mass or less.
- the lower limit is preferably 15 parts by mass or more, more preferably 20 parts by mass or more.
- the total content with Pigment Green 36 is preferably 90 to 100% by mass, more preferably 95 to 100% by mass, even more preferably 99 to 100% by mass.
- the coloring composition of the present invention may contain coloring agents other than unsubstituted copper phthalocyanine pigments and halogenated copper phthalocyanine pigments (hereinafter also referred to as other coloring agents).
- the content of other colorants in the colorant is preferably 20% by mass or less, more preferably 10% by mass or less, and even more preferably 5% by mass or less, from the viewpoint of color separation. It is particularly preferred to be substantially free of other colorants.
- the case where the coloring agent used in the coloring composition of the present invention does not substantially contain other coloring agents means that the content of other coloring agents in the coloring agent is less than 0.5% by mass. It means that it is preferably less than 0.1% by mass, and more preferably does not contain other coloring agents.
- coloring agents include chromatic coloring agents such as yellow coloring agents, green coloring agents, red coloring agents, blue coloring agents, purple coloring agents, and orange coloring agents.
- Other colorants may be pigments or dyes. A pigment and a dye may be used in combination. Examples of pigments include those shown below.
- the content of the coloring agent in the total solid content of the coloring composition is preferably 20 to 70% by mass.
- the upper limit is preferably 67% by mass or less, more preferably 64% by mass or less.
- the lower limit is preferably 22% by mass or more, more preferably 25% by mass or more.
- the content of the unsubstituted copper phthalocyanine pigment in the total mass of the colorant is preferably 10% by mass or more, more preferably 12% by mass or more, and even more preferably 15% by mass or more. .
- the upper limit is preferably 60% by mass or less, more preferably 55% by mass or less, and even more preferably 50% by mass or less.
- the content of the halogenated copper phthalocyanine pigment in the total mass of the colorant is preferably 40% by mass or more, more preferably 45% by mass or more, and even more preferably 50% by mass or more.
- the upper limit is preferably 85% by mass or less, more preferably 75% by mass or less, and even more preferably 65% by mass or less.
- the total content of the unsubstituted copper phthalocyanine pigment and the halogenated copper phthalocyanine pigment in the total weight of the colorant is preferably 70 to 100% by mass, more preferably 80 to 100% by mass. , more preferably 85 to 100% by mass.
- the ratio of the unsubstituted copper phthalocyanine pigment and the halogenated copper phthalocyanine pigment in the colorant is 120 to 600 parts by mass of the halogenated copper phthalocyanine pigment per 100 parts by mass of the unsubstituted copper phthalocyanine pigment. is preferred, 140 to 400 parts by weight is more preferred, and 160 to 200 parts by weight is even more preferred.
- the content of Pigment Blue 15:4 is preferably 10% by mass or more, more preferably 12% by mass or more, and even more preferably 15% by mass or more.
- the upper limit is preferably 60% by mass or less, more preferably 55% by mass or less, and even more preferably 50% by mass or less.
- the content of Pigment Green 7 is preferably 40% by mass or more, more preferably 45% by mass or more, and even more preferably 50% by mass or more.
- the upper limit is preferably 80% by mass or less, more preferably 70% by mass or less, and even more preferably 62% by mass or less.
- the total content with Pigment Green 7 is preferably 75 to 100% by mass, more preferably 80 to 100% by mass, even more preferably 85 to 100% by mass.
- C.I. I. Pigment Blue 15:4 and C.I. I. Pigment Green 7 and C.I. I. Pigment Blue 15:4 for 100 parts by weight of C.I. I. Pigment Green 7 is preferably 120 to 500 parts by mass, more preferably 140 to 400 parts by mass, even more preferably 160 to 300 parts by mass.
- the content of the unsubstituted copper phthalocyanine pigment in the total solid content of the coloring composition is preferably 10 to 50% by mass.
- the upper limit is preferably 45% by mass or less, more preferably 40% by mass or less, and even more preferably 35% by mass or less.
- the lower limit is preferably 12% by mass or more, more preferably 14% by mass or more, and even more preferably 16% by mass or more.
- the content of Pigment Blue 15:4 is preferably 10 to 50% by mass.
- the upper limit is preferably 45% by mass or less, more preferably 40% by mass or less, and even more preferably 35% by mass or less.
- the lower limit is preferably 12% by mass or more, more preferably 14% by mass or more, and even more preferably 16% by mass or more.
- the coloring composition of the present invention contains a resin.
- the resin is blended, for example, for dispersing a pigment or the like in a coloring composition or as a binder.
- a resin mainly used for dispersing a pigment or the like in a coloring composition is also called a dispersant.
- such uses of the resin are only examples, and the resin can be used for purposes other than such uses.
- the weight average molecular weight (Mw) of the resin is preferably 3,000 to 2,000,000.
- the upper limit is preferably 1,000,000 or less, more preferably 500,000 or less.
- the lower limit is preferably 4000 or more, more preferably 5000 or more.
- resins examples include (meth)acrylic resins, epoxy resins, (meth)acrylamide resins, ene-thiol resins, polycarbonate resins, polyether resins, polyarylate resins, polysulfone resins, polyethersulfone resins, polyphenylene resins, and polyarylene resins.
- ether phosphine oxide resins polyimide resins, polyamideimide resins, polyolefin resins, cyclic olefin resins, polyester resins, styrene resins, siloxane resins and the like.
- the resin described in the examples of International Publication No.
- the resin it is preferable to use a resin having an acid group.
- acid groups include carboxy groups, phosphoric acid groups, sulfo groups, and phenolic hydroxy groups.
- the acid value of the resin having acid groups is preferably 30-500 mgKOH/g.
- the lower limit is more preferably 40 mgKOH/g or more, particularly preferably 50 mgKOH/g or more.
- the upper limit is more preferably 400 mgKOH/g or less, still more preferably 300 mgKOH/g or less, and particularly preferably 200 mgKOH/g or less.
- the weight average molecular weight (Mw) of the acid group-containing resin is preferably 5,000 to 100,000, more preferably 5,000 to 50,000.
- the number average molecular weight (Mn) of the resin having an acid group is preferably 1,000 to 20,000.
- the acid group-containing resin preferably contains an acid group-containing repeating unit, and more preferably contains 5 to 70 mol % of the acid group-containing repeating unit in the total repeating units of the resin.
- the upper limit of the content of repeating units having an acid group is preferably 50 mol % or less, more preferably 30 mol % or less.
- the lower limit of the content of repeating units having an acid group is preferably 10 mol % or more, more preferably 20 mol % or more.
- resin having an acid group JP 2012-208494, paragraph numbers 0558 to 0571 (corresponding US Patent Application Publication No. 2012/0235099, paragraph numbers 0685 to 0700), JP 2012-198408
- the descriptions in paragraphs 0076 to 0099 of the publication can be referred to, and the contents thereof are incorporated herein.
- resin which has an acid group can also use a commercial item.
- the method for introducing the acid group into the resin is not particularly limited, but includes, for example, the method described in Japanese Patent No. 6349629 .
- a method for introducing an acid group into a resin a method of reacting an acid anhydride with a hydroxy group generated by a ring-opening reaction of an epoxy group to introduce an acid group can also be mentioned.
- the coloring composition of the present invention also preferably contains a resin having a basic group.
- the resin having a basic group is preferably a resin containing a repeating unit having a basic group in its side chain. It is more preferably a polymer, and more preferably a block copolymer having a repeating unit having a basic group on its side chain and a repeating unit containing no basic group. Resins having basic groups can also be used as dispersants.
- the amine value of the resin having basic groups is preferably 5-300 mgKOH/g.
- the lower limit is preferably 10 mgKOH/g or more, more preferably 20 mgKOH/g or more.
- the upper limit is preferably 200 mgKOH/g or less, more preferably 100 mgKOH/g or less.
- resins having basic groups include DISPERBYK-161, 162, 163, 164, 166, 167, 168, 174, 182, 183, 184, 185, 2000, 2001, 2050, 2150, 2163, 2164, BYK-LPN6919 (manufactured by BYK-Chemie), Solsperse 11200, 13240, 13650, 13940, 24000, 26000, 28000, 32000, 32500, 32550, 32600, 33000, 34750, 35100, 35200, 37500, 33090500, 39090500, 390500 56000, 7100 (manufactured by Nippon Lubrizol), Efka PX 4300, 4330, 4046, 4060, 4080 (manufactured by BASF) and the like.
- the resin having a basic group is a block copolymer (B) described in paragraph numbers 0063 to 0112 of JP-A-2014-219665, and described in paragraph numbers 0046-0076 of JP-A-2018-156021. It is also possible to use the block copolymer A1 described above and vinyl resins having basic groups described in paragraphs 0150 to 0153 of JP-A-2019-184763, the contents of which are incorporated herein.
- the coloring composition of the present invention preferably contains a resin having an acid group and a resin having a basic group. According to this aspect, the storage stability of the coloring composition can be further improved.
- a resin having an acid group and a resin having a basic group are used in combination, the content of the resin having a basic group is 20 to 500 parts by mass with respect to 100 parts by mass of the resin having an acid group. It is preferably from 30 to 300 parts by mass, and even more preferably from 50 to 200 parts by mass.
- the resin is derived from a monomer component containing a compound represented by the following formula (ED1) and/or a compound represented by the following formula (ED2) (hereinafter, these compounds may be referred to as an "ether dimer"). It is also preferable to use a resin containing a repeating unit that
- R 1 and R 2 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 25 carbon atoms which may have a substituent.
- R represents a hydrogen atom or an organic group having 1 to 30 carbon atoms.
- 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 0-15.
- the number of carbon atoms in the alkylene group represented by R 21 and R 22 is preferably 1 to 10, more preferably 1 to 5, even more preferably 1 to 3, particularly 2 or 3.
- 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 formula (X) include ethylene oxide- or propylene oxide-modified (meth)acrylate of paracumylphenol.
- Commercially available products include Aronix M-110 (manufactured by Toagosei Co., Ltd.).
- crosslinkable groups include ethylenically unsaturated bond-containing groups and cyclic ether groups.
- Examples of ethylenically unsaturated bond-containing groups include vinyl groups, styrene groups, (meth)allyl groups, and (meth)acryloyl groups.
- Examples of the cyclic ether group include an epoxy group and an oxetanyl group, with the epoxy group being preferred.
- the epoxy group may be a cycloaliphatic epoxy group.
- the alicyclic epoxy group means a monovalent functional group having a cyclic structure in which an epoxy ring and a saturated hydrocarbon ring are condensed.
- the cyclic ether group is preferably at least one selected from the group represented by the formula (e-1) and the group represented by the formula (e-2), and the group represented by the formula (e-2) It is more preferable that the group is When n in formula (e-1) is 0, the group represented by formula (e-1) is an epoxy group, and when n is 1, it is represented by formula (e-1) The group is an oxetanyl group. Also, the group represented by formula (e-2) is an alicyclic epoxy group.
- R E1 represents a hydrogen atom or an alkyl group, n represents 0 or 1, * represents a bond; in formula (e-2), ring A E1 represents an aliphatic hydrocarbon represents a ring, and * represents a bond.
- the number of carbon atoms in the alkyl group represented by R E1 is preferably 1 to 20, more preferably 1 to 10, still more preferably 1 to 5, and particularly preferably 1 to 3.
- the alkyl group represented by R E1 is preferably linear or branched, more preferably linear.
- R E1 is preferably a hydrogen atom.
- R 1 E1 is preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
- formula (e-1) is represented by formula (e-1a) below.
- the aliphatic hydrocarbon ring represented by ring A E1 in formula (e-2) may be a monocyclic aliphatic hydrocarbon ring or a condensed aliphatic hydrocarbon ring.
- the aliphatic hydrocarbon ring represented by Ring A E1 may have a crosslinked structure.
- a condensed aliphatic hydrocarbon ring is preferable because a film having excellent light resistance can be easily formed, and a condensed aliphatic hydrocarbon ring having a crosslinked structure is preferable.
- aliphatic hydrocarbon ring represented by ring A E1 include groups represented by formulas (e-2-1) to (e-2-4) shown below, and formula (e-2 -3) and the group represented by formula (e-2-4) are preferred.
- the groups represented by formulas (e-2-1) to (e-2-4) may further have a substituent.
- * represents a bond.
- repeating units having a cyclic ether group include repeating units represented by formula (A1).
- X a1 represents a trivalent linking group
- L a1 represents a single bond or a divalent linking group
- Z a1 represents a cyclic ether group.
- Examples of the trivalent linking group represented by X a1 in the formula (A1) include a poly(meth)acrylic linking group, a polyalkyleneimine linking group, a polyester linking group, a polyurethane linking group, a polyurea linking group, and a polyamide linking group.
- Linking groups, polyether-based linking groups, polystyrene-based linking groups, bisphenol-based linking groups, novolac-based linking groups, etc. poly(meth)acrylic-based linking groups, polyether-based linking groups, polyester-based linking groups, bisphenol-based linking groups, etc.
- a linking group and a novolac linking group are preferred, a polyether linking group, a novolac linking group and a poly(meth)acrylic linking group are more preferred, and a poly(meth)acrylic linking group is even more preferred.
- the divalent linking group represented by L a1 in formula (A1) includes an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms), —NH— , --SO--, --SO 2 --, --CO--, --O--, --COO--, --OCO--, --S-- and groups formed by combining two or more of these.
- the alkylene group may be linear, branched or cyclic, preferably linear or branched. Moreover, the alkylene group may have a substituent or may be unsubstituted. A hydroxy group, an alkoxy group, etc. are mentioned as a substituent.
- the cyclic ether group represented by Z a1 in formula (A1) includes an epoxy group and an oxetanyl group, preferably an epoxy group. Further, the cyclic ether group represented by Z a1 is preferably a group represented by formula (e-1) or a group represented by formula (e-2), and a group represented by formula (e-2) It is more preferable that the group is
- the resin having a cyclic ether group is preferably a resin having at least one repeating unit selected from repeating units represented by formula (1) and repeating units represented by formula (2).
- the resin may contain only one of the repeating units represented by the formula (1) and the repeating unit represented by the formula (2), and is represented by the formula (1)
- Each of repeating units and repeating units represented by formula (2) may be included.
- the ratio of the repeating unit represented by the formula (1) to the repeating unit represented by the formula (2) is the molar ratio of the repeating unit represented by the formula (1): the formula
- the repeating unit represented by (2) is preferably from 5:95 to 95:5, more preferably from 10:90 to 90:10, even more preferably from 20:80 to 80:20. .
- L1 represents a single bond or a divalent linking group
- R1 represents a hydrogen atom or a substituent.
- the substituent represented by R 1 includes an alkyl group and an aryl group, preferably an alkyl group.
- the number of carbon atoms in the alkyl group is preferably 1-10, more preferably 1-5, more preferably 1-3.
- R 1 is preferably a hydrogen atom or a methyl group.
- the divalent linking group represented by L 1 includes an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms), -NH-, -SO-, -SO 2 -, -CO-, -O-, -COO-, -OCO-, -S- and groups formed by combining two or more of these.
- the alkylene group may be linear, branched or cyclic, preferably linear or branched.
- the alkylene group may have a substituent or may be unsubstituted. A hydroxy group, an alkoxy group, etc. are mentioned as a substituent.
- the content of repeating units having a cyclic ether group in the resin having a cyclic ether group is preferably 1 to 100 mol% of the total repeating units of the resin having a cyclic ether group.
- the upper limit is preferably 90 mol % or less, more preferably 80 mol % or less.
- the lower limit is preferably 2 mol % or more, more preferably 3 mol % or more.
- the resin having a cyclic ether group may have other repeating units in addition to the repeating unit having a cyclic ether group.
- Other repeating units include a repeating unit having an acid group (hereinafter also referred to as repeating unit B-1) and a repeating unit having a group in which the acid group is protected with a protecting group (hereinafter also referred to as repeating unit B-2). , a repeating unit having an ethylenically unsaturated bond-containing group (hereinafter also referred to as repeating unit B-3).
- Examples of the acid group of the repeating unit B-1 and the acid group protected by the protecting group of the repeating unit B-2 include a phenolic hydroxy group, a carboxy group, a sulfo group, and a phosphoric acid group. , phenolic hydroxy group or carboxy group, more preferably carboxy group.
- Examples of the protective group for protecting the acid group in the repeating unit B-2 include groups that are decomposed and eliminated by the action of an acid or base.
- the protecting group is preferably a group represented by any one of formulas (Y1) to (Y5), and is a group represented by formula (Y3) or formula (Y5) because it is easy to deprotect. is more preferred.
- R Y1 to R Y3 each independently represent an alkyl group, and two of R Y1 to R Y3 may combine to form a ring;
- R Y4 to R Y6 each independently represent an alkyl group, and two of R Y4 to R Y6 may combine to form a ring;
- R Y7 and R Y8 each independently represent a hydrogen atom, an alkyl group or an aryl group, at least one of R Y7 and R Y8 is an alkyl group or an aryl group, and R Y9 is an alkyl represents a group or an aryl group, and R Y7 or R Y8 and R Y9 may combine to form a ring;
- Ar Y1 represents an aryl group
- R Y10 represents an alkyl group or an aryl group;
- R Y11 represents an alkyl group or an aryl group.
- the number of carbon atoms in the alkyl groups represented by R Y1 to R Y3 in formula (Y1) is preferably 1 to 12, more preferably 1 to 6, even more preferably 1 to 4.
- the alkyl group may be linear, branched, or cyclic, but preferably linear or branched.
- two of R Y1 to R Y3 may combine to form a ring.
- Examples of the ring formed by combining two of R Y1 to R Y3 include monocyclic cycloalkyl groups such as cyclopentyl group and cyclohexyl group, norbornyl group, tetracyclodecanyl group, tetracyclododecanyl group, and adamantyl.
- a monocyclic cycloalkyl group having 5 to 6 carbon atoms is preferred.
- one of the ring-constituting methylene groups may be replaced with a heteroatom such as an oxygen atom or a heteroatom-containing group such as a carbonyl group.
- the number of carbon atoms in the alkyl groups represented by R Y4 to R Y6 in formula (Y2) is preferably 1-12, more preferably 1-6, and even more preferably 1-4.
- the alkyl group may be linear, branched, or cyclic, but preferably linear or branched. At least two of R Y4 to R Y6 in formula (Y2) are preferably methyl groups. In formula (Y2), two of R Y4 to R Y6 may combine to form a ring.
- the ring to be formed includes the ring described in formula (Y1).
- R Y7 and R Y8 each independently represent a hydrogen atom, an alkyl group or an aryl group, at least one of R Y7 and R Y8 is an alkyl group or an aryl group, and R Y9 is an alkyl represents a group or an aryl group, and R Y7 or R Y8 and R Y9 may combine to form a ring.
- Alkyl groups may be linear, branched, or cyclic.
- the number of carbon atoms in the alkyl group is preferably 1-12, more preferably 1-6, even more preferably 1-4.
- the aryl group preferably has 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms.
- Examples of the ring formed by combining R Y7 or R Y8 with R Y9 include a tetrahydrofuranyl group and a tetrahydropyranyl group.
- R Y7 or R Y8 and R Y9 preferably combine to form a ring.
- one of R Y7 and R Y8 is preferably a hydrogen atom.
- Ar Y1 represents an aryl group
- R Y10 represents an alkyl group or an aryl group
- Ar Y1 and R Y10 may combine with each other to form a ring.
- the number of carbon atoms in the alkyl group is preferably 1-12, more preferably 1-6, even more preferably 1-4.
- the aryl group preferably has 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms.
- R Y10 is preferably an alkyl group.
- R Y11 represents an alkyl group or an aryl group, preferably an alkyl group.
- the number of carbon atoms in the alkyl group is preferably 1-12, more preferably 1-6, even more preferably 1-4.
- the aryl group preferably has 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms.
- the molecular weight of the protective group is preferably 40-200, more preferably 40-150, even more preferably 40-120. If the molecular weight of the protecting group is within the above range, a colored composition having excellent storage stability and excellent curability at low temperatures can be obtained.
- protecting groups include 1-methoxyethyl group, 1-ethoxyethyl group, 1-n-propoxyethyl group, 1-n-butoxyethyl group, 1-t-butoxyethyl group and 1-cyclopentyloxyethyl group.
- Examples of the ethylenically unsaturated bond-containing group possessed by the repeating unit B-3 include a vinyl group, a styrene group, a (meth)allyl group, and a (meth)acryloyl group.
- repeating unit B-1 examples include repeating units represented by the following formula (B1). Further, repeating units B-2 include repeating units represented by the following formula (B2). Further, the repeating unit B-3 includes a repeating unit represented by the following formula (B3).
- X b1 represents a trivalent linking group
- L b1 represents a single bond or a divalent linking group
- Z b1 represents an acid group.
- X b2 represents a trivalent linking group
- L b2 represents a single bond or a divalent linking group
- Z b2 represents a group in which an acid group is protected with a protecting group.
- X b3 represents a trivalent linking group
- L b3 represents a single bond or a divalent linking group
- Z b3 represents an ethylenically unsaturated bond-containing group.
- the trivalent linking group represented by X b1 in formula (B1), the trivalent linking group represented by X b2 in formula (B2) and the trivalent linking group represented by X b3 in formula (B3) are not particularly limited. do not have.
- poly(meth)acrylic linking group, polyalkyleneimine linking group, polyester linking group, polyurethane linking group, polyurea linking group, polyamide linking group, polyether linking group, polystyrene linking group, bisphenol -based linking group, novolak-based linking group, etc. preferably poly(meth)acrylic-based linking group, polyether-based linking group, polyester-based linking group, bisphenol-based linking group and novolak-based linking group, poly(meth)acrylic System linking groups are more preferred.
- the divalent linking group represented by L b1 in formula (B1), the divalent linking group represented by L b2 in formula (B2) and the divalent linking group represented by L b3 in formula (B3) include an alkylene group ( alkylene group preferably having 1 to 12 carbon atoms), arylene group (preferably arylene group having 6 to 20 carbon atoms), -NH-, -SO-, -SO 2 -, -CO-, -O-, -COO -, -OCO-, -S- and groups formed by combining two or more of these.
- the alkylene group may be linear, branched or cyclic, preferably linear or branched.
- the alkylene group may have a substituent or may be unsubstituted. A hydroxy group, an alkoxy group, etc. are mentioned as a substituent.
- the acid group represented by Z b1 in formula (B1) includes a phenolic hydroxy group, a carboxy group, a sulfo group, and a phosphoric acid group, preferably a phenolic hydroxy group or a carboxy group, and a carboxy group. is more preferred.
- Examples of the group in which the acid group represented by Z b2 of the formula (B2) is protected by a protecting group include groups in which the acid group is protected by a group represented by any one of the formulas (Y1) to (Y5) described above. It is preferable that the acid group is a group protected by a group represented by formula (Y3) or formula (Y5).
- Examples of the acid group include a phenolic hydroxy group, a carboxyl group, a sulfo group and a phosphoric acid group, preferably a phenolic hydroxy group or a carboxyl group, more preferably a carboxyl group.
- Examples of the ethylenically unsaturated bond-containing group represented by Zb3 in formula (B3) include a vinyl group, a styrene group, a (meth)allyl group, and a (meth)acryloyl group.
- the content of the unit B-1 in the resin having a cyclic ether group is 5 to 85 mol% of the total repeating units of the resin having a cyclic ether group.
- the upper limit is preferably 60 mol % or less, more preferably 40 mol % or less.
- the lower limit is preferably 8 mol% or more, more preferably 10 mol% or more.
- the content of the unit B-2 in the resin having a cyclic ether group is 1 to 65 mol% of the total repeating units of the resin having a cyclic ether group.
- the upper limit is preferably 45 mol % or less, more preferably 30 mol % or less.
- the lower limit is preferably 2 mol % or more, more preferably 3 mol % or more.
- the resin having a cyclic ether group contains each of the repeating unit B-1 and the repeating unit B-2, the resin having a cyclic ether group contains 0 repeating units B-2 per 1 mol of the repeating units B-1. It preferably contains 4 to 3.2 mol, more preferably 0.8 to 2.8 mol, even more preferably 1.2 to 2.4 mol.
- the content of the unit B-3 in the resin having a cyclic ether group is 1 to 65 mol% of the total repeating units of the resin having a cyclic ether group.
- the upper limit is preferably 45 mol % or less, more preferably 30 mol % or less.
- the lower limit is preferably 2 mol % or more, more preferably 3 mol % or more.
- a resin having a cyclic ether group preferably further contains a repeating unit having an aromatic hydrocarbon ring.
- the aromatic hydrocarbon ring is preferably a benzene ring or a naphthalene ring, more preferably a benzene ring.
- the aromatic hydrocarbon ring may have a substituent.
- An alkyl group etc. are mentioned as a substituent.
- the content of the repeating unit having an aromatic hydrocarbon ring is 1 to 65 in all repeating units of the resin having a cyclic ether group.
- Mole % is preferred.
- the upper limit is preferably 45 mol % or less, more preferably 30 mol % or less.
- the lower limit is preferably 2 mol % or more, more preferably 3 mol % or more.
- Repeating units having an aromatic hydrocarbon ring include repeating units derived from monofunctional polymerizable compounds having an aromatic hydrocarbon ring, such as vinyl toluene and benzyl (meth)acrylate.
- resins having a cyclic ether group include, for example, naphthalene-modified epoxy resins such as EPICLON HP5000 and EPICLON HP4032D (manufactured by DIC Corporation).
- naphthalene-modified epoxy resins such as EPICLON HP5000 and EPICLON HP4032D (manufactured by DIC Corporation).
- alkyldiphenol-type epoxy resins include EPICLON 820 (manufactured by DIC Corporation).
- jER825, jER827, jER828, jER834, jER1001, jER1002, jER1003, jER1055, jER1007, jER1009, jER1010 (manufactured by Mitsubishi Chemical Corporation), EPICLON860, EPICLON1050, EPICLON1051, EPICLON1055 (and Co., Ltd.) and the like.
- Phenol novolac type epoxy resins include jER152, jER154, jER157S70, jER157S65 (manufactured by Mitsubishi Chemical Corporation), EPICLON N-740, EPICLON N-770, EPICLON N-775 (manufactured by DIC Corporation), and the like. mentioned.
- EPICLON N-660, EPICLON N-665, EPICLON N-670, EPICLON N-673, EPICLON N-680, EPICLON N-690, EPICLON N-695 (manufactured by DIC Corporation) as cresol novolak type epoxy resins , and EOCN-1020 (manufactured by Nippon Kayaku Co., Ltd.).
- ADEKA RESIN EP-4080S, EP-4085S, EP-4088S manufactured by ADEKA Corporation
- Celoxide 2021P Celoxide 2081, Celoxide 2083, Celoxide 2085, EHPE3150, EPOLEAD PB 3600, EPOLEAD PB 4700 (manufactured by Daicel Corporation), Denacol EX-212L, EX-214L, EX-216L, EX-321L, EX-850L (manufactured by Nagase ChemteX Corporation) and the like.
- resin Ac a resin having an aromatic carboxy group
- the aromatic carboxy group may be contained in the main chain of the repeating unit or may be contained in the side chain of the repeating unit.
- the aromatic carboxy group is preferably contained in the main chain of the repeating unit.
- an aromatic carboxy group is a group having a structure in which one or more carboxy groups are bonded to an aromatic ring.
- the number of carboxy groups bonded to the aromatic ring is preferably 1-4, more preferably 1-2.
- Resin Ac is preferably a resin containing at least one repeating unit selected from repeating units represented by formula (Ac-1) and repeating units represented by formula (Ac-2).
- Ar 1 represents a group containing an aromatic carboxyl group
- L 1 represents -COO- or -CONH-
- L 2 represents a divalent linking group
- Ar 10 represents a group containing an aromatic carboxyl group
- L 11 represents -COO- or -CONH-
- L 12 represents a trivalent linking group
- P 10 represents a polymer represents a chain.
- aromatic carboxy group-containing group represented by Ar 1 in formula (Ac-1) examples include structures derived from aromatic tricarboxylic acid anhydrides, structures derived from aromatic tetracarboxylic acid anhydrides, and the like.
- Aromatic tricarboxylic anhydrides and aromatic tetracarboxylic anhydrides include compounds having the following structures.
- Q 1 is a single bond, -O-, -CO-, -COOCH 2 CH 2 OCO-, -SO 2 -, -C(CF 3 ) 2 -, represented by the following formula (Q-1) or a group represented by the following formula (Q-2).
- the group containing an aromatic carboxyl group represented by Ar 1 may have a crosslinkable group.
- the crosslinkable group is preferably an ethylenically unsaturated bond-containing group and a cyclic ether group, more preferably an ethylenically unsaturated bond-containing group.
- Specific examples of the group containing an aromatic carboxy group represented by Ar 1 include a group represented by formula (Ar-11), a group represented by formula (Ar-12), and a group represented by formula (Ar-13). and the like.
- n1 represents an integer of 1 to 4, preferably 1 or 2, more preferably 2.
- n2 represents an integer of 1 to 8, preferably an integer of 1 to 4, more preferably 1 or 2, and still more preferably 2.
- n3 and n4 each independently represent an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 1 or 2, preferably 1 More preferred. However, at least one of n3 and n4 is an integer of 1 or more.
- Q 1 is a single bond, -O-, -CO-, -COOCH 2 CH 2 OCO-, -SO 2 -, -C(CF 3 ) 2 -, the above formula (Q- 1) or a group represented by the above formula (Q-2).
- * 1 represents the bonding position with L1.
- L 1 represents -COO- or -CONH-, preferably -COO-.
- the divalent linking group represented by L 2 in formula (Ac-1) includes an alkylene group, an arylene group, -O-, -CO-, -COO-, -OCO-, -NH-, -S- and these A group obtained by combining two or more of The number of carbon atoms in the alkylene group is preferably 1-30, more preferably 1-20, even more preferably 1-15.
- 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.
- An alkylene group and an arylene group may have a substituent. A hydroxy group etc.
- the divalent linking group represented by L 2 is preferably a group represented by -L 2a -O-.
- L 2a is an alkylene group; an arylene group; a combination of an alkylene group and an arylene group; at least one selected from an alkylene group and an arylene group; Examples include groups in which at least one selected from —NH— and —S— are combined, and alkylene groups are preferred.
- the number of carbon atoms in the alkylene group is preferably 1-30, more preferably 1-20, even more preferably 1-15.
- the alkylene group may be linear, branched or cyclic. An alkylene group and an arylene group may have a substituent. A hydroxy group etc. are mentioned as a substituent.
- the group containing an aromatic carboxy group represented by Ar 10 in formula (Ac-2) has the same meaning as Ar 1 in formula (Ac-1), and the preferred range is also the same.
- L 11 represents -COO- or -CONH-, preferably -COO-.
- the trivalent linking group represented by L 12 in formula (Ac-2) includes a hydrocarbon group, -O-, -CO-, -COO-, -OCO-, -NH-, -S- and 2 of these Groups in which more than one species are combined are included.
- Hydrocarbon groups include aliphatic hydrocarbon groups and aromatic hydrocarbon groups. The number of carbon atoms in the aliphatic hydrocarbon group is preferably 1-30, more preferably 1-20, even more preferably 1-15.
- the aliphatic hydrocarbon group may be linear, branched or cyclic. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6-30, more preferably 6-20, even more preferably 6-10.
- the hydrocarbon group may have a substituent. A hydroxy group etc. are mentioned as a substituent.
- the trivalent linking group represented by L 12 is preferably a group represented by formula (L12-1), more preferably a group represented by formula (L12-2).
- L 12b represents a trivalent linking group
- X 1 represents S
- *1 represents the bonding position with L 11 of formula (Ac-2)
- *2 represents formula ( The binding position of Ac- 2 ) with P10 is shown.
- the trivalent linking group represented by L 12b includes a hydrocarbon group; and at least one selected from -O-, -CO-, -COO-, -OCO-, -NH- and -S- and the like, and a hydrocarbon group or a group of a combination of a hydrocarbon group and —O— is preferred.
- L 12c represents a trivalent linking group
- X 1 represents S
- *1 represents the bonding position with L 11 of formula (Ac-2)
- *2 represents formula ( The binding position of Ac- 2 ) with P10 is shown.
- the trivalent linking group represented by L 12c includes a hydrocarbon group; and at least one selected from -O-, -CO-, -COO-, -OCO-, -NH- and -S- and the like, preferably a hydrocarbon group.
- P 10 in formula (Ac-2) represents a polymer chain.
- the polymer chain represented by P10 preferably has at least one repeating unit selected from poly(meth)acrylic repeating units, polyether repeating units, polyester repeating units and polyol repeating units.
- the weight average molecular weight of the polymer chain P10 is preferably 500-20,000 .
- the lower limit is preferably 1000 or more.
- the upper limit is preferably 10,000 or less, more preferably 5,000 or less, and even more preferably 3,000 or less. If the weight average molecular weight of P10 is within the above range, the dispersibility of the pigment in the composition is good.
- the resin having an aromatic carboxyl group is a resin having repeating units represented by formula (Ac-2), this resin is preferably used as a dispersant.
- the polymer chain represented by P10 may contain crosslinkable groups.
- Crosslinkable groups include ethylenically unsaturated bond-containing groups and cyclic ether groups.
- the coloring composition of the present invention preferably contains a resin as a dispersant.
- Dispersants include acidic dispersants (acidic resins) and basic dispersants (basic resins).
- the acidic dispersant (acidic resin) represents a resin in which the amount of acid groups is greater 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 possessed by the acidic dispersant (acidic resin) is preferably a carboxy group.
- the acid value of the acidic dispersant (acidic resin) is preferably 10-105 mgKOH/g.
- a basic dispersant represents a resin in which the amount of basic groups is greater than the amount of acid groups.
- a resin containing more than 50 mol % of basic groups is preferable when the total amount of acid groups and basic groups is 100 mol %.
- the basic group possessed by the basic dispersant is preferably an amino group.
- the resin used as the dispersant is also preferably a graft resin.
- graft resin for details of the graft resin, reference can be made to paragraphs 0025 to 0094 of JP-A-2012-255128, the contents of which are incorporated herein.
- the resin used as the dispersant is also preferably a polyimine-based dispersant containing nitrogen atoms in at least one of its main chain and side chains.
- the polyimine-based dispersant has a main chain having a partial structure having a functional group with a pKa of 14 or less and a side chain having 40 to 10,000 atoms, and at least one of the main chain and the side chain has a basic nitrogen atom.
- a resin having The basic nitrogen atom is not particularly limited as long as it is a nitrogen atom exhibiting basicity.
- the description in paragraphs 0102 to 0166 of JP-A-2012-255128 can be referred to, and the contents thereof are incorporated herein.
- the resin used as the dispersant is also preferably a resin having a structure in which a plurality of polymer chains are bonded to the core.
- resins include, for example, dendrimers (including star polymers). Further, specific examples of dendrimers include polymer compounds C-1 to C-31 described in paragraphs 0196 to 0209 of JP-A-2013-043962.
- the resin used as the dispersant is also preferably a resin containing a repeating unit having an ethylenically unsaturated bond-containing group in its side chain.
- the content of repeating units having an ethylenically unsaturated bond-containing group in the side chain is preferably 10 mol% or more, more preferably 10 to 80 mol%, more preferably 20 to 70, of the total repeating units of the resin. More preferably, it is mol %.
- resins described in JP-A-2018-087939, block copolymers (EB-1) to (EB-9) described in paragraphs 0219 to 0221 of Japanese Patent No. 6432077, Polyethyleneimine having a polyester side chain described in International Publication No. 2016/104803, a block copolymer described in International Publication No. 2019/125940, a block polymer having an acrylamide structural unit described in JP-A-2020-066687 , a block polymer having an acrylamide structural unit described in JP-A-2020-066688, a dispersant described in WO 2016/104803, and the like can also be used.
- Dispersants are also available as commercial products, and specific examples thereof include Disperbyk series manufactured by BYK-Chemie (e.g., Disperbyk-111, 161, 2001, etc.), Solsperse manufactured by Nippon Lubrizol Co., Ltd. series (for example, Solsperse 20000, 76500, etc.), Ajinomoto Fine-Techno Co., Inc. Ajisper series, and the like.
- Dispersants are also available as commercial products, and specific examples thereof include Disperbyk series manufactured by BYK-Chemie (e.g., Disperbyk-111, 161, 2001, etc.), Solsperse manufactured by Nippon Lubrizol Co., Ltd. series (for example, Solsperse 20000, 76500, etc.), Ajinomoto Fine-Techno Co., Inc. Ajisper series, and the like.
- the resin content in the total solid content of the coloring composition is preferably 10 to 60% by mass.
- the upper limit is preferably 55% by mass or less, more preferably 50% by mass or less.
- the lower limit is preferably 15% by mass or more, more preferably 20% by mass or more.
- the coloring composition of the present invention preferably contains 100 to 350 parts by mass of resin, more preferably 120 to 300 parts by mass of resin, with respect to 100 parts by mass of the colorant, and 140 to 250 parts by mass of resin. It is more preferable to include parts by mass.
- the content of the resin having at least one repeating unit selected from the repeating units represented by the above formula (1) and the repeating unit represented by the formula (2) in the resin is 10% by mass or more.
- the coloring composition of the present invention may contain only one resin, or may contain two or more resins. When two or more resins are included, the total amount thereof is preferably within the above range.
- the coloring composition of the present invention contains a polymerizable compound.
- the polymerizable compound include compounds having an ethylenically unsaturated bond-containing group.
- examples of ethylenically unsaturated bond-containing groups include vinyl groups, (meth)allyl groups, and (meth)acryloyl groups.
- 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 monomer, prepolymer, oligomer, etc., but monomer is preferred.
- the molecular weight of the polymerizable compound is preferably 100-3000.
- the upper limit is preferably 2000 or less, more preferably 1500 or less.
- the lower limit is preferably 150 or more, more preferably 250 or more.
- the lower limit is preferably 3 mmol/g or more, more preferably 4 mmol/g or more, and even more preferably 5 mmol/g or more.
- the upper limit is preferably 12 mmol/g or less, more preferably 10 mmol/g or less, and even more preferably 8 mmol/g or less.
- the polymerizable compound is preferably a compound containing 3 or more ethylenically unsaturated bond-containing groups, more preferably a compound containing 4 or more ethylenically unsaturated bond-containing groups.
- the upper limit of the ethylenically unsaturated bond-containing groups is preferably 15 or less, more preferably 10 or less, even more preferably 6 or less, from the viewpoint of the stability of the colored composition over time.
- the polymerizable compound is preferably a tri- or more functional (meth) acrylate compound, more preferably a 3- to 15-functional (meth) acrylate compound, and a 3- to 10-functional (meth) acrylate compound. is more preferred, and tri- to hexa-functional (meth)acrylate compounds are particularly preferred.
- polymerizable compounds examples include dipentaerythritol tri(meth)acrylate, dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, and modified products of these compounds. mentioned.
- Modified compounds include compounds having a structure in which the (meth)acryloyl groups of the above compounds are bonded via an alkyleneoxy group, such as ethoxylated dipentaerythritol hexa(meth)acrylate. Specific examples include compounds represented by formula (Z-4) and compounds represented by formula (Z-5).
- E is each independently -((CH 2 ) y CH 2 O)- or -((CH 2 ) y CH(CH 3 )O)- , y each independently represents an integer of 0 to 10, and each X independently represents a (meth)acryloyl group, a hydrogen atom, or a carboxy group.
- the total number of (meth)acryloyl groups is 3 or 4
- the sum of m is an integer of 0 to 40.
- the total number of (meth)acryloyl groups is 5 or 6
- each n independently represents an integer of 0-10, and the sum of each n is an integer of 0-60.
- m is preferably an integer of 0-6, more preferably an integer of 0-4.
- the sum of m is preferably an integer of 2 to 40, more preferably an integer of 2 to 16, and particularly preferably an integer of 4 to 8.
- n is preferably an integer of 0-6, more preferably an integer of 0-4.
- the sum of n is preferably an integer of 3-60, more preferably an integer of 3-24, and particularly preferably an integer of 6-12.
- E in formula (Z-4) or formula (Z-5), that is, -((CH 2 ) y CH 2 O)- or -((CH 2 ) y CH(CH 3 )O)- is A form in which the end on the oxygen atom side is bonded to X is preferred.
- Polypentaerythritol poly(meth)acrylate represented by the following formula (Z-6) can also be used as the polymerizable compound.
- X 1 to X 6 each independently represent a hydrogen atom or a (meth)acryloyl group, and n represents an integer of 1-10. However, at least one of X 1 to X 6 is a (meth)acryloyl group.
- the polymerizable compound used in the present invention is at least one selected from the group consisting of dipentaerythritol hexa(meth)acrylate, dipentaerythritol penta(meth)acrylate, polypentaerythritol poly(meth)acrylate and modified products thereof. Seeds are preferred.
- Commercially available products include KAYARAD D-310, DPHA, DPEA-12 (manufactured by Nippon Kayaku Co., Ltd.), NK Ester A-DPH-12E, TPOA-50 (manufactured by Shin-Nakamura Chemical Co., Ltd.), etc. mentioned.
- diglycerin EO ethylene oxide modified (meth) acrylate
- pentaerythritol tetra (meth) acrylate manufactured by Shin-Nakamura Chemical Co., Ltd., NK ester A-TMMT
- 1,6-hexanediol diacrylate manufactured by Nippon Kayaku Co., Ltd., KAYARAD HDDA
- RP-1040 manufactured by Nippon Kayaku Co., Ltd.
- Aronix TO-2349 Toagosei Co., Ltd.
- NK Oligo UA-7200 (manufactured by Shin-Nakamura Chemical Co., Ltd.), 8UH-1006, 8UH-1012 (manufactured by Taisei Fine Chemical Co., Ltd.), Light acrylate POB-A0 (manufactured by Kyoeisha Chemical Co., Ltd.), EBECRYL80 (manufactured by Daicel Allnex, amine-containing tetrafunctional acrylate) and the like can also be used.
- trimethylolpropane tri(meth)acrylate trimethylolpropane propyleneoxy-modified tri(meth)acrylate
- trimethylolpropane ethyleneoxy-modified tri(meth)acrylate trimethylolpropane ethyleneoxy-modified tri(meth)acrylate
- ethyleneoxy isocyanurate-modified tri(meth) It is also preferable to use trifunctional (meth)acrylate compounds such as acrylates and pentaerythritol tri(meth)acrylates.
- Commercial products of 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 such as a carboxy group, a sulfo group, or a phosphoric acid group can be used as the polymerizable compound.
- Commercially available products of such compounds include Aronix M-305, M-510, M-520 and Aronix TO-2349 (manufactured by Toagosei Co., Ltd.).
- a compound having a caprolactone structure can also be used as the polymerizable compound.
- the descriptions in paragraphs 0042 to 0045 of JP-A-2013-253224 can be referred to, the contents of which are incorporated herein.
- Compounds having a caprolactone structure include, for example, DPCA-20, DPCA-30, DPCA-60, DPCA-120, etc., which are commercially available as KAYARAD DPCA series from Nippon Kayaku Co., Ltd.
- a polymerizable compound having a fluorene skeleton can also be used.
- Commercially available products include Ogsol EA-0200 and EA-0300 (manufactured by Osaka Gas Chemicals Co., Ltd., (meth)acrylate monomer having a fluorene skeleton).
- the polymerizable compound it is also preferable to use a compound such as toluene that does not substantially contain environmentally regulated substances.
- a compound such as toluene that does not substantially contain environmentally regulated substances.
- Commercially available products of such compounds include KAYARAD DPHA LT and KAYARAD DPEA-12 LT (manufactured by Nippon Kayaku Co., Ltd.).
- urethane acrylates such as those described in Japanese Patent Publication No. 48-041708, Japanese Patent Publication No. 51-037193, Japanese Patent Publication No. 02-032293, and Japanese Patent Publication No. 02-016765
- urethane compounds having an ethylene oxide skeleton described in JP-B-58-049860, JP-B-56-017654, JP-B-62-039417 and JP-B-62-039418.
- the polymerizable compound includes UA-7200 (manufactured by Shin-Nakamura Chemical Co., Ltd.), DPHA-40H (manufactured by Nippon Kayaku Co., Ltd.), UA-306H, UA-306T, UA-306I, AH-600, Commercially available products such as T-600, AI-600, LINC-202UA (manufactured by Kyoeisha Chemical Co., Ltd.) can also be used.
- the content of the polymerizable compound in the total solid content of the coloring composition is preferably 5 to 50% by mass.
- the upper limit is preferably 40% by mass or less, more preferably 30% by mass or less.
- the lower limit is preferably 7% by mass or more, more preferably 10% by mass or more.
- the coloring composition preferably contains 20 to 200 parts by mass of the polymerizable compound with respect to 100 parts by mass of the resin.
- the upper limit is preferably 150 parts by mass or less, more preferably 100 parts by mass or less.
- the lower limit is preferably 30 parts by mass or more, more preferably 40 parts by mass or more.
- the coloring composition of the present invention may contain only one polymerizable compound, or may contain two or more polymerizable compounds. When two or more polymerizable compounds are included, the total amount thereof is preferably within the above range.
- the coloring composition of the present invention contains a photopolymerization initiator.
- the photopolymerization initiator is not particularly limited and can be appropriately selected from known photopolymerization initiators. For example, compounds having photosensitivity to light in the ultraviolet range to the visible range are preferred.
- the photopolymerization initiator is preferably a photoradical polymerization initiator.
- photopolymerization initiators include halogenated hydrocarbon derivatives (e.g., compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazole compounds, oxime compounds, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds and the like.
- halogenated hydrocarbon derivatives e.g., compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.
- acylphosphine compounds e.g., acylphosphine compounds, hexaarylbiimidazole compounds, oxime compounds, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds and the like.
- photopolymerization initiators include trihalomethyltriazine compounds, benzyldimethylketal compounds, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds, acylphosphine compounds, phosphine oxide compounds, metallocene compounds, oxime compounds, hexaarylbi imidazole compounds, onium compounds, benzothiazole compounds, benzophenone compounds, acetophenone compounds, cyclopentadiene-benzene-iron complexes, halomethyloxadiazole compounds and 3-aryl-substituted coumarin compounds, oxime compounds, ⁇ -hydroxyketones compounds, ⁇ -aminoketone compounds, and acylphosphine compounds, more preferably oxime compounds.
- hexaarylbiimidazole compounds include 2,2′,4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-diphenyl-1,1′-biimidazole, etc. is mentioned.
- ⁇ -hydroxyketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (manufactured by IGM Resins B.V.), Irgacure 184, Irgacure 1173, Irgacure 2959, Irgacure 127 (above company) and the like.
- ⁇ -aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (manufactured by IGM Resins B.V.), Irgacure 907, Irgacure 369, Irgacure 369E, Irgacure 379EG (manufactured by Irgacure 369E, Irgacure 379EG). made), etc.
- acylphosphine compounds include Omnirad 819, Omnirad TPO (manufactured by IGM Resins B.V.), Irgacure 819 and Irgacure TPO (manufactured by BASF).
- Examples of oxime compounds include compounds described in JP-A-2001-233842, compounds described in JP-A-2000-080068, compounds described in JP-A-2006-342166, J. Am. C. S. Compounds described in Perkin II (1979, pp.1653-1660); C. S. Compounds described in Perkin II (1979, pp.156-162), compounds described in Journal of Photopolymer Science and Technology (1995, pp.202-232), compounds described in JP-A-2000-066385, Compounds described in JP-A-2004-534797, compounds described in JP-A-2017-019766, compounds described in Patent No.
- oxime compounds include 3-benzoyloxyiminobutane-2-one, 3-acetoxyiminobutane-2-one, 3-propionyloxyiminobutane-2-one, 2-acetoxyiminopentane-3-one, 2-acetoxyimino-1-phenylpropan-1-one, 2-benzoyloxyimino-1-phenylpropan-1-one, 3-(4-toluenesulfonyloxy)iminobutan-2-one, 2-ethoxycarbonyloxyimino -1-phenylpropane-1-one, 1-[4-(phenylthio)phenyl]-3-cyclohexyl-propane-1,2-dione-2-(O-acetyloxime) and the like.
- An oxime compound having a fluorene ring can also be used as the photopolymerization initiator.
- Specific examples of the oxime compound having a fluorene ring include compounds described in JP-A-2014-137466, compounds described in Japanese Patent No. 6636081, and compounds described in Korean Patent Publication No. 10-2016-0109444. mentioned.
- 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 oxime compounds include compounds described in WO2013/083505.
- 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 include compounds described in JP-A-2010-262028, compounds 24, 36 to 40 described in JP-A-2014-500852, and JP-A-2013-164471. and the compound (C-3) of.
- 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 paragraph numbers 0031 to 0047 of JP-A-2013-114249 and paragraph numbers 0008-0012 and 0070-0079 of JP-A-2014-137466; Compounds described in paragraphs 0007 to 0025 of Japanese Patent No. 4223071 and ADEKA Arkles NCI-831 (manufactured by ADEKA Corporation) can be mentioned.
- An oxime compound having a benzofuran skeleton can also be used as the photopolymerization initiator.
- Specific examples include OE-01 to OE-75 described in WO 2015/036910.
- an oxime compound in which a substituent having a hydroxyl 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 2 OX1 in which an electron-withdrawing group is introduced into the aromatic ring (hereinafter also referred to as oxime compound OX) can be used.
- the electron-withdrawing group possessed by 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.
- a benzoyl group may have a substituent.
- substituents include halogen atoms, cyano groups, nitro groups, hydroxy groups, alkyl groups, alkoxy groups, aryl groups, aryloxy groups, heterocyclic groups, heterocyclicoxy groups, alkenyl groups, alkylsulfanyl groups, arylsulfanyl groups, It is preferably 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.
- a sulfanyl group or an amino group is more preferred.
- the oxime compound OX is preferably at least one selected from the compounds represented by the formula (OX1) and the compounds represented by the formula (OX2), more preferably the compound represented by the formula (OX2). preferable.
- R X1 is an alkyl group, alkenyl group, alkoxy group, aryl group, aryloxy group, heterocyclic group, heterocyclicoxy group, alkylsulfanyl group, arylsulfanyl group, alkylsulfinyl group, arylsulfinyl group, alkylsulfonyl arylsulfonyl group, acyl group, acyloxy group, amino group, phosphinoyl group, carbamoyl group or sulfamoyl group.
- R X2 is an alkyl group, alkenyl group, alkoxy group, aryl group, aryloxy group, heterocyclic group, heterocyclicoxy group, alkylsulfanyl group, arylsulfanyl group, alkylsulfinyl group, arylsulfinyl group, alkylsulfonyl group, aryl represents a sulfonyl group, an acyloxy group or an amino group;
- R X3 to R X14 each independently represent a hydrogen atom or a substituent. However, at least one of R X10 to R X14 is an electron-withdrawing group.
- electron-withdrawing groups include acyl groups, nitro groups, trifluoromethyl groups, alkylsulfinyl groups, arylsulfinyl groups, alkylsulfonyl groups, arylsulfonyl groups, and cyano groups, with acyl groups and nitro groups being preferred.
- An acyl group is more preferred, and a benzoyl group is even more preferred, because a film having excellent properties can be easily formed.
- R X12 is an electron-withdrawing group
- R X10 , R X11 , R X13 and R X14 are preferably hydrogen atoms.
- oxime compound OX examples include compounds described in paragraphs 0083 to 0105 of Japanese Patent No. 4600600.
- oxime compounds preferably used in the present invention are shown below, but the present invention is not limited to these.
- the oxime compound is preferably a compound having a maximum absorption wavelength in the wavelength range of 350 to 500 nm, 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 from the viewpoint of sensitivity, more preferably 1000 to 300000, further preferably 2000 to 300000, even more preferably 5000 to 200000. It is particularly preferred to have
- the molar extinction coefficient of a compound can be measured using known methods. For example, it is preferably measured at a concentration of 0.01 g/L using an ethyl acetate solvent 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 B.V.
- a bifunctional or trifunctional or higher functional photoradical polymerization initiator may be used as the photopolymerization initiator.
- a radical photopolymerization initiator two or more radicals are generated from one molecule of the radical photopolymerization initiator, so good sensitivity can be obtained.
- the crystallinity is reduced, the solubility in a solvent or the like is improved, the precipitation becomes difficult over time, and the stability over time of the colored composition can be improved.
- Specific examples of bifunctional or trifunctional or higher photoradical polymerization initiators include Japanese Patent Publication No. 2010-527339, Japanese Patent Publication No. 2011-524436, International Publication No.
- the content of the photopolymerization initiator in the total solid content of the coloring composition is preferably 0.1 to 20% by mass, more preferably 1 to 10% by mass.
- the lower limit is preferably 1.5% by mass or more, more preferably 2% by mass or more, and even more preferably 2.5% by mass or more.
- the upper limit is preferably 9% by mass or less, more preferably 8% by mass or less, and even more preferably 5% by mass or less.
- the coloring composition preferably contains 15 to 100 parts by mass of a photopolymerization initiator with respect to 100 parts by mass of the polymerizable compound.
- the upper limit is preferably 80 parts by mass or less, more preferably 70 parts by mass or less.
- the lower limit is preferably 25 parts by mass or more, more preferably 33 parts by mass or more.
- only one type of photopolymerization initiator may be used, or two or more types may be used. When two or more are used, the total amount thereof is preferably within the above range.
- the coloring composition of the present invention contains an ultraviolet absorber.
- ultraviolet absorber refers to an organic compound having a function of absorbing ultraviolet rays, and means a compound different from a photopolymerization initiator that efficiently generates active species such as radicals upon irradiation with ultraviolet rays. do.
- the ultraviolet absorber is preferably a compound that absorbs ultraviolet rays, converts them into heat energy, and emits it.
- the ultraviolet absorber is preferably a compound that is stable against ultraviolet rays. That is, the ultraviolet absorber is preferably a compound that is resistant to molecular breakage due to reactions such as decomposition, oxidation, and reduction when irradiated with ultraviolet rays.
- the ultraviolet absorber is preferably a compound having a maximum absorption wavelength in the wavelength range of 340 to 420 nm, more preferably a compound having a maximum absorption wavelength in the wavelength range of 345 to 400 nm, and a wavelength of 350 to 390 nm. It is more preferable that the compound has a maximum absorption wavelength in the range of .
- the maximum value of the molar extinction coefficient in the wavelength range of 340 to 420 nm of the ultraviolet absorber is preferably 5000 L mol -1 cm -1 or more, and is preferably 10000 L mol -1 cm -1 or more. More preferably, it is 13000 L ⁇ mol ⁇ 1 ⁇ cm ⁇ 1 or more.
- the upper limit is preferably, for example, 100000 L ⁇ mol ⁇ 1 ⁇ cm ⁇ 1 or less.
- the UV absorber preferably has a ratio of absorbance A2 at a wavelength of 410 nm to absorbance A1 at a wavelength of 365 nm of 0.06 or less, more preferably 0.04 or less, and 0.02 or less. is more preferable.
- UV absorbers include conjugated diene compounds, benzotriazole compounds, dibenzoyl compounds, triazine compounds, benzophenone compounds, salicylate compounds, coumarin compounds, acrylonitrile compounds, benzodithiazole compounds, cinnamic acid compounds, ⁇ - ⁇ unsaturated ketones, carbohydrates, Examples include styryl compounds and merocyanine compounds, and benzotriazole compounds, dibenzoyl compounds and triazine compounds are preferable because they can achieve both improvement in sensitivity dependence on illumination and stability over time of the coloring composition at a high level. .
- the conjugated diene compound is preferably a compound represented by the following formula (UV-1).
- R 1 and R 2 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms, and R 1 and R 2 are They may be the same or different. At least one of R 1 and R 2 is an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms. R 1 and R 2 may form a cyclic amino group together with the nitrogen atom to which R 1 and R 2 are bonded.
- the cyclic amino group includes, for example, a piperidino group, a morpholino group, a pyrrolidino group, a hexahydroazepino group, a piperazino group and the like.
- R 1 and R 2 are each independently preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, and still more preferably an alkyl group having 1 to 5 carbon atoms.
- R 3 and R 4 each independently represent an electron-withdrawing group.
- R 3 and R 4 are each independently an acyl group, a carbamoyl group, an alkyloxycarbonyl group, an aryloxycarbonyl group, a cyano group, a nitro group, an alkylsulfonyl group, an arylsulfonyl group, a sulfonyloxy group, or a sulfamoyl group; and more preferably an acyl group, a carbamoyl group, an alkyloxycarbonyl group, an aryloxycarbonyl group, a cyano group, an alkylsulfonyl group, an arylsulfonyl group, a sulfonyloxy group or a sulfamoyl group.
- R 3 and R 4 may combine with each other to form a cyclic electron-withdrawing group.
- Examples of the cyclic electron-withdrawing group formed by combining R 3 and R 4 include a 6-membered ring containing two carbonyl groups.
- At least one of R 1 , R 2 , R 3 and R 4 of formula (UV-1) may be in the form of a polymer derived from a monomer linked to a vinyl group via a linking group. Alternatively, it may be a copolymer with other monomers.
- UV-1 the descriptions in paragraphs 0024 to 0033 of JP-A-2009-265642 can be referred to, the contents of which are incorporated herein.
- Specific examples of the ultraviolet absorber represented by formula (UV-1) include compounds having the following structures, compounds described in paragraphs 0034 to 0036 of JP-A-2009-265642, and the like.
- Commercially available UV absorbers represented by formula (UV-1) include UV-503 (manufactured by Daito Kagaku Co., Ltd.).
- the dibenzoyl compound is preferably a compound represented by the following formula (UV-2).
- R 101 and R 102 each independently represent a substituent
- m1 and m2 each independently represent an integer of 0-4.
- Substituents represented by R 101 and R 102 include halogen atoms, cyano groups, nitro groups, alkyl groups, aryl groups, heteroaryl groups, alkoxy groups, aryloxy groups, heteroaryloxy groups, alkylthio groups, arylthio groups, heteroaryl a luthio group, -NR U1 R U2 , -COR U3 , -COOR U4 , -OCOR U5 , -NHCOR U6 , -CONR U7 R U8 , -NHCONR U9 R U10 , -NHCOOR U11 , -SO 2 R U12 , -SO 2 OR U13 , —NHSO 2 R U14 and —SO 2 NR U15 R U16 .
- R U1 to R U16 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or an aryl group.
- the substituents represented by R 101 and R 102 are preferably each independently an alkyl group or an alkoxy group.
- the number of carbon atoms in the alkyl group is preferably 1-20, more preferably 1-10.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched, more preferably branched.
- the number of carbon atoms in the alkoxy group is preferably 1-20, more preferably 1-10.
- the alkoxy group is preferably linear or branched, more preferably branched.
- UV-2 a combination in which one of R 101 and R 102 is an alkyl group and the other is an alkoxy group is preferred.
- n1 and m2 each independently represent an integer of 0 to 4.
- m1 and m2 are each independently preferably 0 to 2, more preferably 0 to 1, and particularly preferably 1.
- dibenzoyl compounds include avobenzone.
- Commercially available dibenzoyl compounds include Neo Heliopan 357 (manufactured by Symrise).
- the triazine compound is preferably a compound represented by formula (UV-3-1), formula (UV-3-2) or formula (UV-3-3) below.
- each R d1 is independently a hydrogen atom, an alkyl group having 1 to 15 carbon atoms, an alkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 18 carbon atoms, an alkylaryl group having 7 to 18 carbon atoms, or It represents an arylalkyl group having 7 to 18 carbon atoms.
- Alkyl groups, alkenyl groups, aryl groups, alkylaryl groups and arylalkyl groups may have substituents. Examples of the substituent include the groups described for the substituent Ti shown below.
- R d2 to R d9 are each independently a hydrogen atom, a halogen atom, a hydroxy group, an alkyl group having 1 to 15 carbon atoms, an alkenyl group having 3 to 8 carbon atoms or an aryl group having 6 to 18 carbon atoms, carbon It represents an alkylaryl group having 7 to 18 carbon atoms or an arylalkyl group having 7 to 18 carbon atoms.
- Alkyl groups, alkenyl groups, aryl groups, alkylaryl groups and arylalkyl groups may have substituents. Examples of the substituent include the groups described for the substituent Ti shown below.
- the substituent Ti includes a halogen atom, a cyano group, a nitro group, a hydrocarbon group, a heterocyclic group, -ORti 1 , -CORti 1 , -COORti 1 , -OCORti 1 , -NRti 1 Rti 2 , -NHCORti 1 , - CONRti 1 Rti 2 , -NHCONRti 1 Rti 2 , -NHCOORti 1 , -SRti 1 , -SO 2 Rti 1 , -SO 2 ORti 1 , -NHSO 2 Rti 1 or -SO 2 NRti 1 Rti 2 .
- Rti 1 and Rti 2 each independently represent a hydrogen atom, a hydrocarbon group or a heterocyclic group.
- Rti 1 and Rti 2 may combine to form a ring.
- Halogen atoms include fluorine, chlorine, bromine and iodine atoms.
- Hydrocarbon groups include alkyl groups, alkenyl groups, alkynyl groups, and aryl groups. The number of carbon atoms in the alkyl group is preferably 1-30, more preferably 1-15, even more preferably 1-8.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched, more preferably branched.
- the alkenyl group preferably has 2 to 30 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 8 carbon atoms.
- the alkenyl group may be linear, branched or cyclic, preferably linear or branched.
- the alkynyl group preferably has 2 to 30 carbon atoms, more preferably 2 to 25 carbon atoms.
- the alkynyl group may be linear, branched or cyclic, preferably linear or branched.
- the number of carbon atoms in the aryl group is preferably 6-30, more preferably 6-20, even more preferably 6-12.
- the heterocyclic group may be monocyclic or condensed.
- the heterocyclic group is preferably a monocyclic ring or a condensed ring having 2 to 4 condensed rings.
- the number of heteroatoms constituting the ring of the heterocyclic group is preferably 1-3.
- a heteroatom 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 3-30, more preferably 3-18, and more preferably 3-12.
- a hydrocarbon group and a heterocyclic group may have a substituent or may be unsubstituted. Examples of the substituent include the substituents described for the substituent Ti described above.
- triazine compounds include 2-[4-[(2-hydroxy-3-dodecyloxypropyl)oxy]-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1, 3,5-triazine, 2-[4-[(2-hydroxy-3-tridecyloxypropyl)oxy]-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3 ,5-triazine, 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine; -bis(2-hydroxy-4-propyloxyphenyl)-6-(2,4-dimethylphenyl)-1,3,5-triazine, 2,4-bis(2-hydroxy-3-methyl-4-propyl oxyphenyl)-6-(4-methylphenyl)-1,3,5-triazine, 2,4-bis(2-hydroxy-3-methyl-4-propyl oxyphen
- triazine compounds include TINUVIN 400, TINUVIN 405, TINUVIN 460, TINUVIN 477, TINUVIN 479 (manufactured by BASF), and KEMISORB 102 (manufactured by Chemipro Kasei Co., Ltd.).
- the benzotriazole compound is preferably a compound represented by formula (UV-4) below.
- R e1 to R e3 are each independently a hydrogen atom, a halogen atom, a hydroxy group, an alkyl group having 1 to 9 carbon atoms, an alkoxy group having 1 to 9 carbon atoms, an alkylaryl group having 7 to 18 carbon atoms, or It represents an arylalkyl group having 7 to 18 carbon atoms.
- Alkyl groups, alkylaryl groups and arylalkyl groups may have a substituent. Examples of the substituent include the groups described for the substituent Ti described above, and an alkoxycarbonyl group having 1 to 9 carbon atoms is preferred.
- benzotriazole compounds include 2-(2'-hydroxy-3',5'-di-tert-butylphenyl)-5-chlorobenzotriazole, 2-(2'-hydroxy-3'-tert- Butyl-5'-methylphenyl)-5-chlorobenzotriazole, 2-(2'-hydroxy-3'-tert-amyl-5'-isobutylphenyl)-5-chlorobenzotriazole, 2-(2'-hydroxy -3'-isobutyl-5'-methylphenyl)-5-chlorobenzotriazole, 2-(2'-hydroxy-3'-isobutyl-5'-propylphenyl)-5-chlorobenzotriazole, 2-(2' -hydroxy-3′,5′-di-tert-butylphenyl)benzotriazole, 2-(2′-hydroxy-5′-methylphenyl)benzotriazole, 2-[2′-hydroxy-5′-(1, 1,3,3-t)benz
- TINUVIN P TINUVIN PS
- TINUVIN 99-2 TINUVIN 109
- TINUVIN 326 TINUVIN 326
- TINUVIN 328 TINUVIN 384-2
- TINUVIN 900 TINUVIN 928, TINUVIN 171, TINUVIN 1130
- Sumisorb 200 Sumisorb 250, Sumisorb 300, Sumisorb 340, Sumisorb 350 (manufactured by Sumika Chemtex Co., Ltd.)
- KEMISORB 71, KEMISOLB 73, KEMISOLB 74, KEMISOLB 79, KEMISOLB 279 manufactured by Chemipro Kasei Co., Ltd.
- benzotriazole compound the MYUA series manufactured by Miyoshi Oil and Fat may be used.
- Benzophenone compounds include 2,2′-dihydroxy-4-methoxybenzophenone, 2,2′-dihydroxy-4,4′-dimethoxybenzophenone, 2,2′,4,4′-tetrahydroxybenzophenone, 2-hydroxy- 4-methoxybenzophenone, 2,4-dihydroxybenzophenone, 2-hydroxy-4-octoxybenzophenone and the like.
- benzophenone compounds include UvinulA, Uvinul049, Uvinul3050 (manufactured by BASF), Sumisorb 130 (manufactured by Sumika Chemtex Co., Ltd.), KEMISOLB 10, KEMISOLB 11, KEMISOLB 11S, KEMISOLB 12, and KEMISOLB 111 (all (manufactured by Chemipro Kasei Co., Ltd.) and the like.
- salicylate compounds include phenyl salicylate, p-octylphenyl salicylate, and pt-butylphenyl salicylate.
- Coumarin compounds include, for example, coumarin-4, 4-hydroxycoumarin, and 7-hydroxycoumarin.
- Acrylonitrile compounds include ethyl 2-cyano-3,3-diphenylacrylate and 2-ethylhexyl 2-cyano-3,3-diphenylacrylate.
- the ultraviolet absorber paragraph numbers 0038 to 0052 of JP-A-2009-217221, paragraph numbers 0052-0072 of JP-A-2012-208374, paragraph numbers 0317-0334 of JP-A-2013-068814,
- the compounds described in paragraph numbers 0061 to 0080 of JP 2016-162946, paragraph numbers 0049 to 0059 of Japanese Patent No. 6268967, and paragraph numbers 0059 to 0076 of WO 2016/181987 can also be used.
- the content of the ultraviolet absorber in the total solid form of the coloring composition is preferably 0.1% by mass or more, more preferably 0.3% by mass or more, and 0.5% by mass or more is more preferable, 1% by mass or more is even more preferable, and 1 to 10% by mass is particularly preferable.
- the upper limit of the content of the ultraviolet absorber is preferably 8% by mass or less, more preferably 5% by mass or less.
- the coloring composition preferably contains 10 to 100 parts by mass of the ultraviolet absorber with respect to 100 parts by mass of the photopolymerization initiator.
- the upper limit is preferably 90 parts by mass or less, more preferably 80 parts by mass or less.
- the lower limit is preferably 20 parts by mass or more, more preferably 30 parts by mass or more.
- the coloring composition preferably contains 5 to 50 parts by mass of an ultraviolet absorber with respect to 100 parts by mass of the polymerizable compound.
- the upper limit is preferably 40 parts by mass or less, more preferably 30 parts by mass or less.
- the lower limit is preferably 7 parts by mass or more, more preferably 10 parts by mass or more. If the ratio of the ultraviolet absorber and the polymerizable compound is within the above range, it is effective in improving the illuminance dependence of line width sensitivity.
- One type of ultraviolet absorber may be used alone, or two or more types may be used in combination. When two or more are used in combination, the total of them is within the above range.
- the coloring composition of the present invention contains a solvent.
- An organic solvent is mentioned as a solvent.
- the type of solvent is basically not particularly limited as long as it satisfies the solubility of each component and the coatability of the composition.
- Organic solvents include ester-based solvents, ketone-based solvents, alcohol-based solvents, amide-based solvents, ether-based solvents, and hydrocarbon-based solvents. For these details, reference can be made to paragraph 0223 of WO2015/166779, the content of which is incorporated herein. Ester-based solvents substituted with cyclic alkyl groups and ketone-based solvents substituted with cyclic alkyl groups can also be preferably used.
- organic solvents 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, 2-pentanone, 3-pentanone, 4-heptanone, cyclohexanone, 2-methylcyclohexanone, 3-methylcyclohexanone, 4-methylcyclohexanone, cycloheptanone, cyclooctanone, cyclohexyl acetate, cyclopentanone, ethylcarbitol Acetate, butyl carbitol acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 3-methoxy-N,N-dimethylpropanamide, 3-butoxy-N
- aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) as organic solvents may be better reduced for environmental reasons (e.g., 50 mass ppm (parts per million), 10 mass ppm or less, or 1 mass ppm or less).
- an organic solvent with a low metal content it is preferable to use an organic solvent with a low metal content.
- the metal content of the organic solvent is preferably, for example, 10 mass ppb (parts per billion) or less. If necessary, an organic solvent at a mass ppt (parts per trillion) level may be used, and such an organic solvent is provided, for example, by Toyo Gosei Co., Ltd. (Chemical Daily, November 13, 2015). .
- Examples of methods for removing impurities such as metals from organic solvents include distillation (molecular distillation, thin film distillation, etc.) and filtration using a filter.
- the filter pore size 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 material of the filter is preferably polytetrafluoroethylene, polyethylene or nylon.
- the organic solvent may contain isomers (compounds with the same number of atoms but different structures). Moreover, only one isomer may be contained, or a plurality of isomers 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 10-95% by mass, more preferably 20-90% by mass, and even more preferably 30-90% by mass.
- the colored composition of the present invention does not substantially contain environmentally regulated substances.
- substantially free of environmentally regulated substances means that the content of environmentally regulated substances in the colored composition is 50 ppm by mass or less, preferably 30 ppm by mass or less. , is more preferably 10 mass ppm or less, and particularly preferably 1 mass ppm or less.
- Environmental control substances include, for example, benzene; alkylbenzenes such as toluene and xylene; and halogenated benzenes such as chlorobenzene.
- distillation methods are the stage of raw materials, the stage of reacting raw materials (e.g., resin solution or polyfunctional monomer solution after polymerization), or the stage of colored compositions 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.
- Pigment derivatives are used, for example, as dispersing aids.
- Pigment derivatives include compounds having a structure in which an acid group or a basic group is bonded to a pigment skeleton.
- Dye skeletons constituting pigment derivatives include quinoline dye skeletons, benzimidazolone dye skeletons, benzoisoindole dye skeletons, benzothiazole dye skeletons, iminium dye skeletons, squarylium dye skeletons, croconium dye skeletons, oxonol dye skeletons, and pyrrolopyrrole dye skeletons.
- diketopyrrolopyrrole dye skeleton azo dye skeleton, azomethine dye skeleton, phthalocyanine dye skeleton, naphthalocyanine dye skeleton, anthraquinone dye skeleton, quinacridone dye skeleton, dioxazine dye skeleton, perinone dye skeleton, perylene dye skeleton, thioindigo dye skeleton, Isoindoline dye skeletons, isoindolinone dye skeletons, quinophthalone dye skeletons, iminium dye skeletons, dithiol dye skeletons, triarylmethane dye skeletons, pyrromethene dye skeletons, and the like can be mentioned.
- the acid group includes a carboxy group, a sulfo group, a phosphoric acid group, a boronic acid group, a carboxylic acid amide group, a sulfonic acid amide group, an imidic acid group and salts thereof.
- 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 ions, imidazolium ions, pyridinium ions, phosphonium ion and the like.
- the carboxylic acid amide group a group represented by —NHCOR X1 is preferable.
- sulfonic acid amide group a group represented by —NHSO 2 R X2 is preferable.
- the imidic acid group is preferably a group represented by —SO 2 NHSO 2 R X3 , —CONHSO 2 R X4 , —CONHCOR X5 or —SO 2 NHCOR X6 , more preferably —SO 2 NHSO 2 R X3 .
- R X1 to R X6 each independently represent an alkyl group or an aryl group.
- the alkyl groups and aryl groups represented by R X1 to R X6 may have substituents.
- the substituent is preferably a halogen atom, more preferably a fluorine atom.
- Basic groups include amino groups, pyridinyl groups and salts thereof, salts of ammonium groups, and phthalimidomethyl groups.
- Atoms or atomic groups constituting salts include hydroxide ions, halogen ions, carboxylate ions, sulfonate ions, and phenoxide ions.
- a pigment derivative having excellent visible transparency (hereinafter also referred to as a transparent pigment derivative) can also be used as the pigment derivative.
- the maximum value ( ⁇ max) of the molar extinction coefficient of the transparent pigment derivative in the wavelength region of 400 to 700 nm is preferably 3000 L ⁇ mol ⁇ 1 ⁇ cm ⁇ 1 or less, and 1000 L ⁇ mol ⁇ 1 ⁇ cm ⁇ 1 or less. is more preferable, and 100 L ⁇ mol ⁇ 1 ⁇ cm ⁇ 1 or less is even more 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 the examples described later, JP-A-56-118462, JP-A-63-264674, JP-A-01-217077, and JP-A-03-009961. , JP-A-03-026767, JP-A-03-153780, JP-A-03-045662, JP-A-04-285669, JP-A-06-145546, JP-A-06-212088, Patent JP-A-06-240158, JP-A-10-030063, JP-A-10-195326, paragraph numbers 0086 to 0098 of WO 2011/024896, paragraph numbers 0063 to 0094 of WO 2012/102399 , Paragraph No.
- the content of the pigment derivative is preferably 1 to 30 parts by mass, more preferably 2 to 15 parts by mass, and even more preferably 4 to 10 parts by mass with respect to 100 parts by mass of the pigment. Only one pigment derivative may be used, or two or more pigment derivatives may be used in combination. When two or more are used in combination, the total amount thereof is preferably within the above range.
- the coloring composition of the present invention can also contain a polyalkyleneimine.
- Polyalkyleneimines are used, for example, as dispersing aids for pigments.
- a dispersing aid is a material for enhancing dispersibility of a pigment in a coloring composition.
- Polyalkyleneimine is a polymer obtained by ring-opening polymerization of alkyleneimine.
- a polyalkyleneimine is a polymer having a branched structure each containing a primary amino group, a secondary amino group, and a tertiary amino group.
- the alkyleneimine preferably has 2 to 6 carbon atoms, more preferably 2 to 4 carbon atoms, still more preferably 2 or 3 carbon atoms, and particularly preferably 2 carbon atoms.
- the molecular weight of the polyalkyleneimine is preferably 200 or more, more preferably 250 or more.
- the upper limit is preferably 100,000 or less, more preferably 50,000 or less, even more preferably 10,000 or less, and particularly preferably 2,000 or less.
- the molecular weight of the polyalkyleneimine when the molecular weight can be calculated from the structural formula, the molecular weight of the polyalkyleneimine is the value calculated from the structural formula.
- the molecular weight of the specific amine compound cannot be calculated from the structural formula or is difficult to calculate, the value of the number average molecular weight measured by the boiling point elevation method is used.
- the value of the number average molecular weight measured by the viscosity method is used.
- the value of the number average molecular weight in terms of polystyrene measured by the GPC (gel permeation chromatography) method is used.
- the amine value of the polyalkyleneimine is preferably 5 mmol/g or more, more preferably 10 mmol/g or more, and even more preferably 15 mmol/g or more.
- alkyleneimine examples include ethyleneimine, propyleneimine, 1,2-butyleneimine, 2,3-butyleneimine and the like, preferably ethyleneimine or propyleneimine, more preferably ethyleneimine. preferable. It is particularly preferred that the polyalkyleneimine is polyethyleneimine. In addition, the polyethyleneimine preferably contains 10 mol% or more, more preferably 20 mol% or more, of the primary amino group with respect to the total of the primary amino group, the secondary amino group and the tertiary amino group. , more preferably 30 mol % or more.
- Commercial products of polyethyleneimine include Epomin SP-003, SP-006, SP-012, SP-018, SP-200, P-1000 (manufactured by Nippon Shokubai Co., Ltd.).
- the content of polyalkyleneimine in the total solid content of the coloring composition is preferably 0.1 to 5% by mass.
- the lower limit is preferably 0.2% by mass or more, more preferably 0.5% by mass or more, and even more preferably 1% by mass or more.
- the upper limit is preferably 4.5% by mass or less, more preferably 4% by mass or less, and even more preferably 3% by mass or less.
- the content of the polyalkyleneimine is preferably 0.5 to 20 parts by mass with respect to 100 parts by mass of the pigment.
- the lower limit is preferably 0.6 parts by mass or more, more preferably 1 part by mass or more, and even more preferably 2 parts by mass or more.
- the upper limit is preferably 10 parts by mass or less, more preferably 8 parts by mass or less. Only one kind of polyalkyleneimine may be used, or two or more kinds thereof may be used. When two or more types are used, the total amount thereof is preferably within the above range.
- the coloring composition of the present invention can contain a curing accelerator.
- Curing accelerators include thiol compounds, methylol compounds, amine compounds, phosphonium salt compounds, amidine salt compounds, amide compounds, base generators, isocyanate compounds, alkoxysilane compounds, onium salt compounds and the like.
- the curing accelerator include compounds described in paragraph numbers 0094 to 0097 of WO 2018/056189, compounds described in paragraph numbers 0246 to 0253 of JP 2015-034963, JP 2013-041165 Compounds described in paragraph numbers 0186 to 0251 of the publication, ionic compounds described in JP 2014-055114, compounds described in paragraph numbers 0071 to 0080 of JP 2012-150180, JP 2011-253054 Alkoxysilane compounds having an epoxy group described in JP-A-2005-200157, compounds described in paragraphs 0085 to 0092 of Japanese Patent No. 5765059, and carboxy group-containing epoxy curing agents described in JP-A-2017-036379.
- the content of the curing accelerator in the total solid content of the coloring composition is preferably 0.3 to 8.9% by mass, more preferably 0.8 to 6.4% by mass.
- the coloring composition of the present invention can contain a polymerization inhibitor.
- Polymerization inhibitors include hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4′-thiobis(3-methyl-6-tert-butylphenol), 2,2′-methylenebis(4-methyl-6-t-butylphenol), N-nitrosophenylhydroxyamine salts (ammonium salts, cerous salts, etc.). Among them, p-methoxyphenol is preferred.
- the content of the polymerization inhibitor in the total solid content of the coloring composition is preferably 0.0001 to 5% by mass. Only one type of polymerization inhibitor may be used, or two or more types may be used. When two or more types are used, the total amount is preferably within the above range.
- the coloring composition of the present invention can contain a silane coupling agent.
- a 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 bonded to a silicon atom and capable of forming a siloxane bond by at least one of hydrolysis reaction and condensation reaction.
- Hydrolyzable groups include, for example, halogen atoms, alkoxy groups, acyloxy groups and the like, with alkoxy groups being preferred. That is, the silane coupling agent is preferably a compound having an alkoxysilyl group.
- Examples of functional groups other than hydrolyzable groups include vinyl group, (meth)allyl group, (meth)acryloyl group, mercapto group, epoxy group, oxetanyl group, amino group, ureido group, sulfide group and isocyanate group. , phenyl group, etc., and amino group, (meth)acryloyl group and epoxy group are preferred.
- 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 KBM
- silane coupling agent examples include compounds described in paragraph numbers 0018 to 0036 of JP-A-2009-288703 and compounds described in paragraph numbers 0056-0066 of JP-A-2009-242604. , the contents of which 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. Only one kind of silane coupling agent may be used, or two or more kinds thereof may be used. When two or more types are used, the total amount is preferably within the above range.
- the coloring composition of the present invention can contain a surfactant.
- a surfactant various surfactants such as fluorine surfactants, nonionic surfactants, cationic surfactants, anionic surfactants, and silicone surfactants can be used.
- the surfactant is preferably a silicone-based surfactant or a fluorine-based surfactant.
- surfactants reference can be made to surfactants described in paragraphs 0238-0245 of WO2015/166779, the contents of which are incorporated herein.
- the fluorine content in the fluorine-based surfactant is preferably 3-40% by mass, more preferably 5-30% by mass, and particularly preferably 7-25% by mass.
- a fluorosurfactant having a fluorine content within this range is effective in terms of uniformity of the thickness of the coating film and saving liquid, and has good solubility in the coloring composition.
- JP 2014-041318 Paragraph Nos. 0060 to 0064 (corresponding International Publication No. 2014/017669 Paragraph Nos. 0060 to 0064) surfactants described in, JP 2011- Examples include surfactants described in paragraphs 0117 to 0132 of JP-A-132503 and surfactants described in JP-A-2020-008634, the contents of which are incorporated herein.
- Commercially available fluorosurfactants include Megafac F-171, F-172, F-173, F-176, F-177, F-141, F-142, F-143 and F-144.
- the fluorosurfactant has a molecular structure with a functional group containing a fluorine atom, and an acrylic compound in which the functional group containing a fluorine atom is cleaved and the fluorine atom volatilizes when heat is applied is also suitable.
- fluorine-based surfactants include MegaFac DS series manufactured by DIC Corporation (Chemical Daily (February 22, 2016), Nikkei Sangyo Shimbun (February 23, 2016)), for example, Mega Fac DS-21.
- fluorosurfactant 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 as the fluorosurfactant.
- fluorosurfactants include fluorosurfactants described in JP-A-2016-216602, the contents of which are incorporated herein.
- a block polymer can also be used as the fluorosurfactant.
- the fluorosurfactant has 2 or more (preferably 5 or more) repeating units derived from a (meth)acrylate compound having a fluorine atom and an alkyleneoxy group (preferably an ethyleneoxy group or a propyleneoxy group) (meta).
- 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 fluorine-based surfactants used in the present invention.
- the weight average molecular weight of the above compound is preferably 3000-50000, for example 14000. In the above compounds, % indicating the ratio of repeating units is mol%.
- a fluoropolymer having an ethylenically unsaturated bond-containing group in a side chain can also be used as the fluorosurfactant.
- Specific examples include compounds described in paragraph numbers 0050 to 0090 and paragraph numbers 0289 to 0295 of JP-A-2010-164965, MEGAFACE RS-101, RS-102 and RS-718K manufactured by DIC Corporation, and RS-72-K.
- compounds described in paragraphs 0015 to 0158 of JP-A-2015-117327 can also be used.
- a fluorine-containing imide salt compound represented by formula (fi-1) is also preferable to use as a surfactant.
- m represents 1 or 2
- n represents an integer of 1 to 4
- a represents 1 or 2
- X a+ is an a-valent metal ion, primary ammonium ion, Represents secondary ammonium ion, tertiary ammonium ion, quaternary ammonium ion or NH 4 + .
- Nonionic surfactants include glycerol, trimethylolpropane, trimethylolethane and their ethoxylates and propoxylates (e.g., glycerol propoxylate, glycerol ethoxylate, etc.), polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, Polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene nonylphenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, sorbitan fatty acid ester, Pluronic L10, L31, L61, L62, 10R5, 17R2, 25R2 (BASF company), Tetronic 304, 701, 704, 901, 904, 150R1 (manufactured by BASF), Solsperse 20000 (manufactured by Nippon Lubrizol Co., Ltd.), NCW-101, NCW-1001, NCW-1002 (Fuji
- Silicone surfactants include DOWSIL SH8400, SH8400 FLUID, FZ-2122, 67 Additive, 74 Additive, M Additive, SF 8419 OIL (manufactured by Dow Toray Industries, Inc.), TSF-4300, TSF-4445, TSF-4460, TSF-4452 (manufactured by Momentive Performance Materials), KP-341, KF-6000, KF-6001, KF-6002, KF-6003 (manufactured by Shin-Etsu Chemical Co., Ltd.) , BYK-307, BYK-322, BYK-323, BYK-330, BYK-333, BYK-3760, BYK-UV3510 (manufactured by BYK-Chemie) and the like.
- a compound having the following structure can also be used as the silicone-based surfactant.
- 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% by mass to 3.0% by mass. Only one type of surfactant may be used, or two or more types may be used. When two or more types are used, the total amount is preferably within the above range.
- the coloring composition of the present invention can contain an antioxidant.
- Antioxidants include phenol compounds, phosphite ester compounds, thioether compounds and the like. Any phenolic compound known as a phenolic antioxidant can be used as the phenolic compound. Preferred phenolic compounds include hindered phenolic compounds. A compound having a substituent at a site adjacent to the phenolic hydroxy group (ortho position) is preferred. As the aforementioned substituent, a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms is preferred.
- the antioxidant is also preferably a compound having a phenol group and a phosphite ester group in the same molecule.
- Phosphorus-based antioxidants can also be suitably used as antioxidants.
- a phosphorus antioxidant tris[2-[[2,4,8,10-tetrakis(1,1-dimethylethyl)dibenzo[d,f][1,3,2]dioxaphosphepin-6 -yl]oxy]ethyl]amine, tris[2-[(4,6,9,11-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphepin-2-yl ) oxy]ethyl]amine, ethyl bis(2,4-di-tert-butyl-6-methylphenyl) phosphite, and the like.
- antioxidants examples include Adekastab AO-20, Adekastab AO-30, Adekastab AO-40, Adekastab AO-50, Adekastab AO-50F, Adekastab AO-60, Adekastab AO-60G, Adekastab AO-80. , ADEKA STAB AO-330 (manufactured by ADEKA Corporation) and the like.
- antioxidants are compounds described in paragraph numbers 0023 to 0048 of Japanese Patent No. 6268967, compounds described in WO 2017/006600, compounds described in WO 2017/164024, Compounds 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 thereof may be used. When two or more kinds are used, the total amount is preferably within the above range.
- the coloring composition of the present invention may optionally contain sensitizers, curing accelerators, fillers, thermosetting accelerators, plasticizers and other auxiliaries (e.g., conductive particles, antifoaming agents, flame retardants, leveling agents, release accelerators, fragrances, surface tension modifiers, chain transfer agents, etc.). Properties such as film physical properties can be adjusted by appropriately containing these components. These components are described, for example, from paragraph number 0183 of JP-A-2012-003225 (paragraph number 0237 of corresponding US Patent Application Publication No. 2013/0034812), paragraph of JP-A-2008-250074 The descriptions of numbers 0101 to 0104, 0107 to 0109, etc.
- auxiliaries e.g., conductive particles, antifoaming agents, flame retardants, leveling agents, release accelerators, fragrances, surface tension modifiers, chain transfer agents, etc.
- the coloring composition of the present invention may contain a latent antioxidant, if desired.
- the latent antioxidant is a compound in which the site functioning as an antioxidant is protected by a protective group, and is heated at 100 to 250°C, or heated at 80 to 200°C in the presence of an acid/base catalyst.
- a compound that functions as an antioxidant by removing the protective group by the reaction is exemplified.
- Examples of latent antioxidants include compounds described in International Publication No. 2014/021023, International Publication No. 2017/030005, and JP-A-2017-008219.
- Commercially available latent antioxidants include ADEKA Arkles GPA-5001 (manufactured by ADEKA Co., Ltd.).
- the coloring composition of the present invention may contain a metal oxide in order to adjust the refractive index of the resulting film.
- metal oxides include TiO 2 , ZrO 2 , Al 2 O 3 and SiO 2 .
- the primary particle size of the metal oxide is preferably 1 to 100 nm, more preferably 3 to 70 nm, even more preferably 5 to 50 nm.
- Metal oxides may have a core-shell structure. Moreover, in this case, the core portion may be hollow.
- the coloring composition of the present invention may contain a light resistance improver.
- a light resistance improver compounds described in paragraph numbers 0036 to 0037 of JP-A-2017-198787, compounds described in paragraph numbers 0029-0034 of JP-A-2017-146350, JP-A-2017-129774 Compounds described in paragraph numbers 0036 to 0037, 0049 to 0052 of JP 2017-129674 JP 2017-129674 paragraph numbers 0031 to 0034, 0058 to 0059 compounds described in JP 2017-122803 paragraph numbers 0036 to 0037 , compounds described in 0051 to 0054, compounds described in paragraph numbers 0025 to 0039 of WO 2017/164127, compounds described in paragraph numbers 0034 to 0047 of JP 2017-186546, JP 2015-025116 Compounds described in paragraph numbers 0019 to 0041 of JP-A-2012-145604, compounds described in paragraph numbers 0101-0125 of JP-A-2012-103475, compounds
- the coloring composition of the present invention preferably does not substantially contain terephthalic acid ester.
- substantially free means that the content of 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.
- perfluoroalkylsulfonic acid and its salts may be regulated.
- perfluoroalkylsulfonic acid especially perfluoroalkylsulfonic acid having 6 to 8 carbon atoms in the perfluoroalkyl group
- fluoroalkylcarboxylic acid especially perfluoroalkylcarboxylic acid having 6 to 8 carbon atoms in the perfluoroalkyl group
- its salt is 0.01ppb to 1,000ppb with respect to the total solid content of the coloring composition.
- the coloring composition of the present invention may be substantially free of perfluoroalkylsulfonic acid and its salts and perfluoroalkylcarboxylic acid and its salts.
- a compound that can substitute for perfluoroalkylsulfonic acid and its salt and a compound that can substitute for perfluoroalkylcarboxylic acid and its salt, perfluoroalkylsulfonic acid and its salt, and perfluoroalkylcarboxylic acid and salts thereof may be selected.
- Examples of compounds that can substitute for regulated compounds include compounds that are excluded from the scope of regulation due to differences in the number of carbon atoms in perfluoroalkyl groups. However, the above content does not prevent the use of perfluoroalkylsulfonic acid and its salts, and perfluoroalkylcarboxylic acid and its salts.
- the coloring composition of the present invention may contain perfluoroalkylsulfonic acid and its salts and perfluoroalkylcarboxylic acid and its salts within the maximum permissible range.
- 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, 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 state (flatness, etc.) and adjusting the film thickness.
- the viscosity value can be appropriately selected as necessary, and is preferably, for example, 0.3 mPa ⁇ s to 50 mPa ⁇ s, more preferably 0.5 mPa ⁇ s to 20 mPa ⁇ s at 25°C.
- 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 the coloring composition is not particularly limited, and known containers can be used.
- a storage container a multi-layer bottle whose inner wall is composed of 6 types and 6 layers of resins and a bottle with a 7-layer structure of 6 types of resins for the purpose of suppressing the contamination of raw materials and coloring compositions. It is also preferred 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 deterioration of components.
- the coloring composition of the present invention can be prepared by mixing the aforementioned ingredients.
- all components may be simultaneously dissolved and / or dispersed in a solvent to prepare a colored composition, and if necessary, each component may be appropriately mixed into two or more solutions or dispersions. , these may be mixed at the time of use (at the time of coating) to prepare a colored composition.
- a process of dispersing the pigment when preparing the coloring composition.
- mechanical forces used for dispersing pigments include 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.
- 2015-157893 can be suitably used.
- the particles may be made finer in the salt milling process.
- Materials, equipment, processing conditions, etc. used in the salt milling step can be referred to, for example, Japanese Patent Application Laid-Open Nos. 2015-194521 and 2012-046629.
- 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) (including high-density, ultra-high-molecular-weight polyolefin resin) and other materials.
- PP polypropylene
- nylon including high density polypropylene
- nylon including high density polypropylene
- the pore size of the filter is preferably 0.01-7.0 ⁇ m, more preferably 0.01-3.0 ⁇ m, and even more preferably 0.05-0.5 ⁇ m. If the pore diameter of the filter is within the above range, fine foreign matter can be removed more reliably.
- the pore size value of the filter reference can be made to the filter manufacturer's nominal value.
- Various filters provided by Nihon Pall Co., Ltd. (DFA4201NIEY, DFA4201NAEY, DFA4201J006P, etc.), Advantech Toyo Co., Ltd., Nippon Entegris Co., Ltd. (former Japan Microlith Co., Ltd.), Kitz Micro Filter Co., Ltd., etc. can be used as the filter. .
- fibrous filter media include polypropylene fibers, nylon fibers, and glass fibers.
- 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.
- filters When using filters, different filters (eg, a first filter and a second filter, etc.) may be combined. At that time, filtration with each filter may be performed only once, or may be performed twice or more. Also, filters with different pore sizes within the range described above may be combined. Further, the filtration with the first filter may be performed only on the dispersion liquid, and after mixing other components, the filtration with the second filter may be performed. In addition, the filter can be appropriately selected according to the hydrophilicity/hydrophobicity of the composition.
- the film of the present invention is a film obtained from the colored composition of the present invention described above.
- the film of the present invention can be used for color filters and the like. Specifically, it can be preferably used as a colored layer (pixel) of a color filter, and more preferably used as a cyan pixel.
- the film thickness of the film of the present invention can be appropriately adjusted depending on the purpose, but is preferably 0.1 to 20 ⁇ m.
- the upper limit of the film thickness is preferably 10 ⁇ m or less, more preferably 5 ⁇ m or less, still more preferably 3 ⁇ m or less, and particularly preferably 1.5 ⁇ m or less.
- the lower limit of the film thickness is preferably 0.2 ⁇ m or more, more preferably 0.3 ⁇ m or more.
- the film of the present invention preferably has an average transmittance of 75% or more, more preferably 80% or more, and even more preferably 85% or more in the wavelength range of 400 to 450 nm.
- the upper limit can be 100% or less.
- the film of the present invention preferably has an average transmittance of 30% or less, more preferably 25% or less, and further preferably 20% or less for light in the wavelength range of 650 to 700 nm. preferable.
- the lower limit can be 0% or more.
- the wavelength of light exhibiting a transmittance of 50% preferably exists in the wavelength range of 560 to 590 nm, more preferably in the wavelength range of 565 to 585 nm. More preferably it is in the range of 580 nm.
- a method for forming pixels includes a step of applying a coloring composition onto a support to form a coloring composition layer, a step of exposing the coloring composition layer in a pattern, and developing the coloring composition layer after exposure. and a step of performing.
- the colored composition layer is formed by applying the colored composition onto the support.
- the support is not particularly limited and can be appropriately selected depending on the application. Examples thereof include glass substrates and silicon substrates, and silicon substrates are preferred. Also, 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.
- the silicon substrate is formed with a black matrix that isolates each pixel.
- the silicon substrate may be provided with an underlying layer for improving adhesion with the upper layer, preventing diffusion of substances, or flattening the substrate surface.
- the underlayer may be formed using a composition obtained by removing the coloring agent from the colored composition described herein, or a composition containing the resin, polymerizable compound, surfactant, etc. described herein. good.
- the surface contact angle of the underlayer is preferably 20 to 70° when measured with diiodomethane. Further, it is preferably 30 to 80° when measured with water.
- a known method can be used as a method for applying the coloring composition.
- dropping method drop cast
- slit coating method spray method
- roll coating method spin coating
- methods described in publications inkjet
- ejection system printing ejection system printing such as nozzle jet, flexographic printing, screen printing, gravure printing, reverse offset printing, metal mask printing, etc. various printing methods; a transfer method using a mold or the like; and a nanoimprint method.
- the application method for inkjet is not particularly limited.
- the colored composition layer formed on the support may be dried (pre-baked). Pre-baking may not be performed when the film is manufactured by a low-temperature process.
- the pre-baking temperature is preferably 150° C. or lower, more preferably 120° C. or lower, and even more preferably 110° C. or lower.
- the lower limit can be, for example, 50° C. or higher, and can also be 80° C. or higher.
- the pre-bake time is preferably 10 to 300 seconds, more preferably 40 to 250 seconds, even more preferably 80 to 220 seconds. Pre-baking can be performed using 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 through a mask having a predetermined mask pattern using a stepper exposure machine, a scanner exposure machine, or the like. Thereby, the exposed portion can be cured.
- Radiation (light) that can be used for exposure includes g-line, i-line, and the like.
- Light with a wavelength of 300 nm or less (preferably light with a wavelength of 180 to 300 nm) can also be used.
- Light having a wavelength of 300 nm or less includes KrF rays (wavelength: 248 nm), ArF rays (wavelength: 193 nm), etc., and KrF rays (wavelength: 248 nm) are preferred.
- a long-wave light source of 300 nm or more can also be used.
- the light when exposing, the light may be continuously irradiated and exposed, or may be irradiated and exposed in pulses (pulse exposure).
- pulse exposure is an exposure method in which exposure is performed by repeating light irradiation and rest in short-time (for example, millisecond level or less) cycles.
- the dose is, for example, preferably 0.03 to 2.5 J/cm 2 , more preferably 0.05 to 1.0 J/cm 2 .
- the oxygen concentration at the time of exposure can be selected as appropriate.
- the exposure may be in an oxygen-free atmosphere, or in a high-oxygen atmosphere with an oxygen concentration exceeding 21% by volume (for example, 22% by volume, 30% by volume, or 50% by volume).
- the exposure illuminance can be set as appropriate, and is usually selected from the range of 1000 W/m 2 to 100000 W/m 2 (eg, 5000 W/m 2 , 15000 W/m 2 or 35000 W/m 2 ). can be done.
- the oxygen concentration and exposure illuminance may be appropriately combined.
- the illuminance may be 10000 W/m 2 at an oxygen concentration of 10% by volume and 20000 W/m 2 at an oxygen concentration of 35% by volume.
- the unexposed areas of the colored composition layer are removed by development to form a pattern (pixels).
- the development and removal of the unexposed portion of the colored composition layer can be performed using a developer.
- the unexposed portion of the colored composition layer in the exposure step is eluted into the developer, leaving only the photocured portion.
- the temperature of the developer is preferably 20 to 30° C., for example.
- the development time is preferably 20 to 180 seconds. Further, in order to improve the residue removability, the step of shaking off the developer every 60 seconds and then supplying new developer may be repeated several times.
- the developer includes an organic solvent, an alkaline developer, etc., and an alkaline developer is preferably used.
- an alkaline developer an alkaline aqueous solution (alkali developer) obtained by diluting an alkaline agent with pure water is preferable.
- alkaline agents include ammonia, ethylamine, diethylamine, dimethylethanolamine, diglycolamine, diethanolamine, hydroxylamine, 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
- examples include organic alkaline compounds and inorganic alkaline compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogen carbonate, sodium silicate and sodium metasilicate.
- a compound having a large molecular weight is preferable for the alkaline agent from the standpoint 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 transportation and storage convenience, the developer may be produced once as a concentrated solution and then diluted to the required concentration when used. Although the dilution ratio is not particularly limited, it can be set, for example, in the range of 1.5 to 100 times. It is also preferable to wash (rinse) with pure water after development. Rinsing is preferably carried out by supplying a rinsing solution to the developed colored composition layer while rotating the support on which the developed colored composition layer is formed.
- the nozzle for discharging the rinsing liquid from the central portion of the support to the peripheral portion of the support.
- the moving speed of the nozzle may be gradually decreased.
- Additional exposure processing and post-baking are post-development curing treatments for complete curing.
- the heating temperature in post-baking is, for example, preferably 100 to 240.degree. C., more preferably 200 to 240.degree.
- Post-baking can be performed continuously or batchwise using a heating means such as a hot plate, a convection oven (hot air circulating dryer), or a high-frequency heater so that the developed film satisfies the above conditions. .
- the light used for exposure preferably has a wavelength of 400 nm or less.
- the additional exposure process may be performed by the method described in Korean Patent Publication No. 10-2017-0122130.
- the color filter of the invention has the film of the invention described above. Preferably, it has the film of the invention as a colored pixel, more preferably as a cyan pixel, of a color filter.
- the color filter of the present invention can be used for solid-state imaging devices, image display devices, and the like.
- the color filter of the present invention preferably has colored pixels of other hues in addition to the pixels of the film of the present invention. Colored pixels of other hues include blue pixels, red pixels, yellow pixels and magenta pixels.
- a preferred embodiment of the color filter of the present invention includes a mode having cyan pixels, yellow pixels, and magenta pixels, which are composed of the film of the present invention.
- the color filter may have a structure in which each color pixel is embedded in a space partitioned by partition walls, for example, in a grid pattern. In this case, the partition wall preferably has a lower refractive index than each color pixel. Moreover, the partition may be formed with the configuration described in US Patent Application Publication No. 2018/0040656.
- the color filter may have a protective layer provided on the surface of the film of the present invention.
- a protective layer By providing the protective layer, it is possible to impart various functions such as blocking oxygen, reducing reflection, making the film hydrophilic and hydrophobic, and blocking light of a specific wavelength (ultraviolet rays, near-infrared rays, etc.).
- the thickness of the protective layer is preferably 0.01-10 ⁇ m, more preferably 0.1-5 ⁇ m.
- Examples of the method for forming the protective layer include a method of applying a resin composition dissolved in an organic solvent, a chemical vapor deposition method, and a method of bonding a molded resin with an adhesive.
- Components constituting the protective layer include (meth)acrylic resins, ene-thiol resins, polycarbonate resins, polyether resins, polyarylate resins, polysulfone resins, polyethersulfone resins, polyphenylene resins, polyarylene ether phosphine oxide resins, and polyimides.
- the protective layer preferably contains a polyol resin, SiO 2 and Si 2 N 4 .
- the protective layer preferably contains a (meth)acrylic resin and a fluororesin.
- a resin composition When a resin composition is applied to form a protective layer, known methods such as spin coating, casting, screen printing, and ink-jetting can be used as methods for applying the resin composition.
- Known organic solvents eg, propylene glycol 1-monomethyl ether 2-acetate, cyclopentanone, ethyl lactate, etc.
- the protective layer is formed by a chemical vapor deposition method
- the chemical vapor deposition method includes known chemical vapor deposition methods (thermal chemical vapor deposition method, plasma chemical vapor deposition method, photochemical vapor deposition method). can be used.
- the protective layer contains organic/inorganic fine particles, absorbers for light of specific wavelengths (e.g., ultraviolet rays, near-infrared rays, etc.), refractive index modifiers, antioxidants, adhesion agents, additives such as surfactants. may contain.
- organic/inorganic fine particles include polymeric fine particles (eg, 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 for light of a specific wavelength.
- the content of these additives can be appropriately adjusted, 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 layers described in paragraphs 0073 to 0092 of JP-A-2017-151176 can also be used.
- the solid-state imaging device of the present invention has the film of the present invention described above.
- the configuration of the solid-state imaging device is not particularly limited as long as it has the film of the present invention and functions as a solid-state imaging device.
- Transfer electrodes made of polysilicon or the like, and a plurality of photodiodes forming the light-receiving area of a solid-state imaging device (such as a CCD (charge-coupled device) image sensor, a CMOS (complementary metal-oxide semiconductor) image sensor, etc.) on a substrate.
- a light-shielding film is provided on the photodiode and the transfer electrode so that only the light-receiving portion of the photodiode is opened. It has a device protective film with a thickness of 1.5 mm, and has a color filter on the device protective film.
- the color filter may have a structure in which each color pixel is embedded in a space partitioned by partition walls, for example, in a grid pattern.
- the partition wall preferably has a lower refractive index than each color pixel. Examples of imaging devices having such a structure include devices described in JP-A-2012-227478, JP-A-2014-179577, and International Publication No. 2018/043654.
- an ultraviolet absorption layer may be provided in the structure of the solid-state imaging device to improve light resistance.
- An imaging device equipped with the solid-state imaging device of the present invention can be used not only for digital cameras and electronic devices having an imaging function (mobile phones, etc.), but also for vehicle-mounted cameras and monitoring cameras.
- the film of the present invention can also be used in image display devices.
- image display devices include liquid crystal display devices and organic electroluminescence display devices.
- electroluminescence display devices For a definition of an image display device and details of each image display device, see, for example, “Electronic Display Device (by Akio Sasaki, Industrial Research Institute, 1990)", “Display Device (by Junsho Ibuki, Sangyo Tosho ( Co., Ltd.) issued in 1989).
- Liquid crystal display devices are described, for example, in “Next Generation Liquid Crystal Display Technology (edited by Tatsuo Uchida, published by Kogyo Choukai Co., Ltd., 1994)". There is no particular limitation on the liquid crystal display device to which the present invention can be applied.
- dispersion liquid A mixed liquid obtained by mixing the materials shown in the table below was mixed and dispersed for 3 hours using a bead mill (zirconia beads with a diameter of 0.1 mm). Then, dispersion treatment was carried out using a high-pressure disperser NANO-3000-10 (manufactured by Nippon BEE Co., Ltd.) with a pressure reduction mechanism under conditions of a pressure of 2000 kg/cm 3 and a flow rate of 500 g/min. This dispersing treatment was repeated 10 times to obtain a dispersion.
- NANO-3000-10 manufactured by Nippon BEE Co., Ltd.
- PG7 C.I. I. Pigment Green 36 (halogenated copper phthalocyanine pigment)
- PG36 C.I. I. Pigment Green 36 (halogenated copper phthalocyanine pigment)
- PB15:4 C.I. I. Pigment Blue 15:4 (unsubstituted copper phthalocyanine pigment)
- PB15:6 C.I. I. Pigment Blue 15:6 (unsubstituted copper phthalocyanine pigment)
- (dispersant) A-1 Resin having the following structure (numerical values attached to the main chain are molar ratios; weight average molecular weight: 11,000)
- A-2 Resin having the following structure (The numerical value attached to the main chain is the molar ratio, and the numerical value attached to the side chain is the number of repeating units. Weight average molecular weight 24000)
- A-3 Resin synthesized by the following method An appropriate amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel and a stirrer, the atmosphere was replaced with nitrogen, and 340 parts by mass of propylene glycol monomethyl ether acetate (PGMEA) was added. and heated to 80° C. with stirring.
- PGMEA propylene glycol monomethyl ether acetate
- the obtained resin had a weight average molecular weight of 9400, a dispersity of 1.89 and an acid value of 114 mgKOH/g.
- A-4 Resin having the following structure (the numerical value attached to the main chain is the molar ratio, and the numerical value attached to the side chain is the number of repeating units. Weight average molecular weight: 20,000)
- A-5 Resin having the following structure (the numerical value attached to the main chain is the molar ratio, and the numerical value attached to the side chain is the number of repeating units. Weight average molecular weight: 16,000)
- A-6 Resin having the following structure (the numerical value attached to the main chain is the molar ratio, and the numerical value attached to the side chain is the number of repeating units. Weight average molecular weight 20000)
- A-7 Resin having the following structure (The numerical value attached to the main chain is the molar ratio, and the numerical value attached to the side chain is the number of repeating units. Weight average molecular weight 7000)
- a coloring composition was produced by mixing the raw materials shown in the table below.
- the unit of the numerical value described in the column of compounding amount is parts by mass.
- Dispersions 1-9 Dispersions 1-9 as described above
- binder B-1 A 40% by mass PGMEA solution of a resin having the following structure (numerical values attached to the main chain are molar ratios; weight average molecular weight: 11000)
- B-2 A 40% by mass propylene glycol monomethyl ether acetate (PGMEA) solution of a resin synthesized by the following method: A flask equipped with a reflux condenser, a dropping funnel and a stirrer is filled with an appropriate amount of nitrogen to replace the nitrogen atmosphere, and PGMEA is added. 371 parts by mass was added and heated to 85° C. while stirring. Next, 54 parts by mass of acrylic acid, 225 parts by mass of a mixture of 3,4-epoxytricyclo[5.2.1.02,6]decane-8 and 9-yl acrylate, and vinyl toluene (isomer mixture). A mixed solution of 81 parts by mass and 80 parts by mass of PGMEA was added dropwise over 4 hours.
- PGMEA propylene glycol monomethyl ether acetate
- a solution prepared by dissolving 30 parts by mass of 2,2-azobis(2,4-dimethylvaleronitrile) as a polymerization initiator in 160 parts by mass of PGMEA was added dropwise over 5 hours. After the completion of dropping the initiator solution, the temperature was kept at 85° C. for 4 hours, and then cooled to room temperature to synthesize a resin.
- the obtained resin had a weight average molecular weight of 10,600, a dispersity of 2.01, and an acid value of 43 mgKOH/g.
- PGMEA was added to adjust the solid content concentration to 40% by mass to obtain Binder B-2.
- B-3 A 40% by mass PGMEA solution of a resin having the following structure (numerical values attached to the main chain are molar ratios; weight average molecular weight: 30,000)
- B-4 A 40% by mass PGMEA solution of a resin having the following structure (values attached to the main chain are mass ratios; weight average molecular weight: 14,600)
- C-1 to C-4 compounds having the following structure C-5: 2,2′,4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-diphenyl-1,1 '-Biimidazole
- D-1 A mixture of compounds having the following structure (a mixture in which the molar ratio of the left compound (hexafunctional (meth)acrylate compound) and the right compound (pentafunctional (meth)acrylate compound) is 7:3)
- D-2 A compound having the following structure
- D-3 A compound having the following structure
- D-4 Trimethylolpropane ethyleneoxy-modified triacrylate (manufactured by Toagosei Co., Ltd., Aronix M-350)
- D-5 EBECRYL80 (manufactured by Daicel Allnex, amine-containing tetrafunctional acrylate)
- D-6 ethoxylated dipentaerythritol hexamethacrylate
- E-1 A compound having the following structure (conjugated diene compound)
- E-2 Neo Heliopan 357 (manufactured by Symrise, Avobenzone)
- E-3 Tinuvin 477 (manufactured by BASF, triazine compound)
- E-4 Tinuvin P (manufactured by BASF, benzotriazole compound)
- E-5 KEMISORB 10 (manufactured by Chemipro Kasei Co., Ltd., benzophenone compound)
- E-6 Sumisorb 200 (manufactured by Sumika Chemtex Co., Ltd., benzotriazole compound)
- F-1 A compound having the following structure (silicone surfactant, hydroxyl value 62 mgKOH/g).
- F-2 A compound having the following structure (weight average molecular weight: 14,000). In the following formulas, % indicating the ratio of repeating units is mol %.
- F-3 Futergent 208G (manufactured by NEOS, fluorosurfactant)
- H-1 compound having the following structure (compound having an epoxy group, weight average molecular weight: 3500)
- H-2 EHPE3150 (manufactured by Daicel Corporation, 1,2-epoxy-4-(2-oxiranyl)cyclohexane adduct of 2,2′-bis(hydroxymethyl)-1-butanol)
- H-3 compound having the following structure (silane coupling agent)
- H-4 3-methacryloxypropyltrimethoxysilane (KBM-503, manufactured by Shin-Etsu Chemical Co., Ltd., silane coupling agent)
- H-5 Adekastab AO-80 (manufactured by ADEKA Corporation, antioxidant)
- the following table shows the ratio (mass ratio) of the unsubstituted copper phthalocyanine pigment in the coloring agent contained in each coloring composition, the C.I. I. Pigment Green 7 (PG7) ratio (mass ratio) and the halogenated copper phthalocyanine pigment C.I. I.
- the ratio (mass ratio) of Pigment Green 36 (PG36) is described.
- the ratio of the content of the resin to the content of the colorant (resin/colorant) is shown in the column of the resin/colorant ratio in the table below.
- the content of the ultraviolet absorbent in the total solid content of the coloring composition is described in the column of the content of the ultraviolet absorbent.
- the content of the photopolymerization initiator in the total solid content of the coloring composition is described in the column of the content of the photopolymerization initiator.
- the coloring composition is applied onto a glass substrate by spin coating, then heat-treated (pre-baked) at 100° C. for 120 seconds using a hot plate, then exposed to i-line at an exposure dose of 1000 mJ/cm 2 , and then , and 200° C. for 5 minutes to form a film with a thickness of 0.6 ⁇ m.
- a spectrometer manufactured by Otsuka Electronics Co., Ltd., MCPD-3000
- the light transmittance (transmittance) in the wavelength range of 400 to 700 nm was measured.
- the average value of transmittance (T1), the average value of transmittance (T2) of light in the wavelength range of 650 to 700 nm, and the wavelength ( ⁇ 50) at which the transmittance is 50% are obtained, respectively, and the spectral characteristics are determined according to the following criteria. evaluated.
- T1 -Average value (T1) of light transmittance in the wavelength range of 400 to 450 nm-
- T2 -Average value (T2) of light transmittance in the wavelength range of 650 to 700 nm-
- ⁇ 50 exists in the wavelength range of 570 nm or more and 580 nm or less.
- B ⁇ 50 exists in the wavelength range of 565 nm or more and less than 570 nm, or in the wavelength range of more than 580 nm and 585 nm or less.
- C ⁇ 50 exists in the wavelength range of 560 nm or more and less than 565 nm, or in the wavelength range of more than 585 nm and 590 nm or less.
- D ⁇ 50 exists in the wavelength range of less than 560 nm or in the wavelength range of more than 590 nm.
- the coloring composition was applied onto a silicon wafer by spin coating, and then heat-treated (pre-baked) at 100° C. for 120 seconds using a hot plate to form a composition layer having a thickness of 0.6 ⁇ m. Then, the composition layer was passed through a mask in which square non-mask portions of 1.0 ⁇ m on a side were arranged in an area of 4 mm ⁇ 3 mm, and an i-line stepper exposure apparatus FPA-3000i5+ (manufactured by Canon Inc.).
- the silicon wafer on which the composition layer after exposure is formed is placed on a horizontal rotating table of a spin shower developing machine (DW-30 type, manufactured by Chemitronics Co., Ltd.), and a developing solution (CD- 2000, Fuji Film Electronic Materials Co., Ltd.), puddle development was performed at 23° C. for 60 seconds.
- DW-30 type manufactured by Chemitronics Co., Ltd.
- CD- 2000 Fuji Film Electronic Materials Co., Ltd.
- Pixels were formed in the same manner as described above, except that the exposure illuminance during exposure was changed to 10000 W/m 2 , 20000 W/m 2 or 30000 W/m 2 to produce substrates with pixels. Pixels on each substrate were divided, cross-sectional SEM images were obtained in the same manner as described above, five pixels were extracted from each cross-sectional SEM image, and the average line width of the five pixels was obtained.
- the substrate with pixels prepared by exposure under the condition of exposure illuminance of 6000 W/m 2 is exposed to A1
- the substrate with pixels prepared by exposure under the condition of exposure illuminance of 10000 W/m 2 is exposed to A2
- the exposure illuminance of 20000 W/m 2 is exposed.
- A3 be the substrate with pixels prepared in this way
- A4 be the substrate with pixels prepared by exposing under the condition of exposure illuminance of 30000 W/m 2 .
- the standard deviation ⁇ of the average value of the line widths of pixels A1 to A4 was obtained, and the illuminance dependence of the line width was evaluated according to the following criteria.
- C The standard deviation ⁇ is 0.5 ⁇ m or more and less than 0.7 ⁇ m.
- D The standard deviation ⁇ is 0.7 ⁇ m or more.
- the coloring composition was applied onto a silicon wafer by spin coating, and then heat-treated (pre-baked) at 100° C. for 120 seconds using a hot plate to form a composition layer having a thickness of 0.6 ⁇ m.
- the coloring composition immediately after manufacture or the coloring composition after storage for 12 months in a constant temperature bath at 5° C. was used as the coloring composition.
- each coloring composition was used after adjusting the temperature to 23°C.
- composition layer was passed through a mask in which square non-mask portions of 1.0 ⁇ m on a side were arranged in an area of 4 mm ⁇ 3 mm, and an i-line stepper exposure apparatus FPA-3000i5+ (manufactured by Canon Inc.). ) was used to irradiate light with a wavelength of 365 nm at an exposure intensity of 10,000 W/m 2 and an exposure dose of 500 mJ/cm 2 .
- FPA-3000i5+ manufactured by Canon Inc.
- the silicon wafer on which the composition layer after exposure is formed is placed on a horizontal rotating table of a spin shower developing machine (DW-30 type, manufactured by Chemitronics Co., Ltd.), and a developing solution (CD- 2000, Fuji Film Electronic Materials Co., Ltd.), puddle development was performed at 23° C. for 60 seconds.
- a spin shower developing machine DW-30 type, manufactured by Chemitronics Co., Ltd.
- a developing solution CD- 2000, Fuji Film Electronic Materials Co., Ltd.
- pure water is supplied from above the center of rotation in a shower from a jetting nozzle to perform a rinsing treatment. manufactured.
- a cross-sectional SEM image was obtained using a scanning electron microscope (manufactured by Hitachi High-Tech Co., Ltd.).
- Rate of change in line width (%) ((average line width 2/average line width 1) - 1) x 100
- the average value 1 of the line width is the average value of the line width of the pixels formed using the coloring composition immediately after production, and the average value 2 of the line width is the coloration after storage for 12 months in a constant temperature bath at 5 ° C. It is the average value of the line width of the pixels formed using the composition.
- B Line width change rate is 5.0% or more and less than 7.5%
- C Line width change rate is 7.5% or more and less than 10.0%
- D Line width change rate is 10.0% or more
- the coloring composition is applied onto a glass substrate by spin coating, then heat-treated (pre-baked) at 100° C. for 120 seconds using a hot plate, then exposed to i-line at an exposure dose of 1000 mJ/cm 2 , and then , and 200° C. for 5 minutes to form a film with a thickness of 0.6 ⁇ m.
- a spectroscope manufactured by Otsuka Electronics Co., Ltd., MCPD-3000
- the obtained film was measured for light transmittance (transmittance) in a wavelength range of 400 to 700 nm.
- the film prepared above was irradiated with light of 100,000 Lux for 2,000 hours using a light resistance tester (super xenon weather meter SX75, manufactured by Suga Test Instruments Co., Ltd.) (total irradiation amount: 200 million Lux hr. ).
- the transmittance of the film after light irradiation was measured, and the light resistance was evaluated according to the following criteria.
- B The integrated value of the transmittance of the film at a wavelength of 400 to 700 nm after light irradiation is 94% or more and less than 98% of the integrated value of the transmittance of the film at a wavelength of 400 to 700 nm before light irradiation.
- C The integrated transmittance of the film at a wavelength of 400 to 700 nm after light irradiation is 90% or more and less than 94% of the integrated transmittance of the film at a wavelength of 400 to 700 nm before light irradiation.
- the integrated value of the transmittance of the film at a wavelength of 400 to 700 nm after light irradiation is less than 90% of the integrated value of the transmittance of the film at a wavelength of 400 to 700 nm before light irradiation.
- the coloring compositions of the examples have evaluation results of A to C for both the illuminance dependence of the line width and the sensitivity over time stability, and the illuminance dependence of the line width is small. Excellent sensitivity stability over time. Also, by using the colored composition of the example, a film having excellent light resistance could be formed. Similar results were obtained when no surfactant was added in Example 1. Similar results were obtained when no polymerization inhibitor was added in Example 1.
- Example 1001 The coloring composition of Example 1 was applied onto a silicon wafer by a spin coating method so that the film thickness after forming the film was 0.6 ⁇ m. Then, using a hot plate, it was heated at 100° C. for 2 minutes. Then, using an i-line stepper exposure apparatus FPA-3000i5+ (manufactured by Canon Inc.), exposure was performed at an exposure amount of 1000 mJ/cm 2 through a 1 ⁇ m square dot pattern mask. Then, using a 0.3 mass % aqueous solution of tetramethylammonium hydroxide (TMAH), puddle development was performed at 23° C. for 60 seconds. After that, it was rinsed with a spin shower and then washed with pure water.
- TMAH tetramethylammonium hydroxide
- the colored composition was patterned by heating at 200° C. for 5 minutes to form cyan pixels.
- the red colored composition and the yellow colored composition were patterned in the same process to sequentially form red pixels and yellow pixels to form a color filter having cyan pixels, red pixels and yellow-isolated pixels.
- a red coloring composition and a yellow coloring composition are mentioned later.
- yellow pixels are formed in a Bayer pattern, and red pixels and cyan pixels are formed in an island pattern in adjacent regions.
- the obtained color filter was incorporated into a solid-state imaging device according to a known method. This solid-state imaging device had a favorable image recognition ability.
- Red colored composition After mixing and stirring the following components, the mixture was filtered through a nylon filter having a pore size of 0.45 ⁇ m (manufactured by Nippon Pall Co., Ltd.) to prepare a red colored composition.
- Red pigment dispersion liquid ... 51.7 parts by mass Resin 101 ... 0.6 parts by mass Polymerizable compound (NK Ester A-DPH-12E, manufactured by Shin-Nakamura Chemical Co., Ltd.) ... 0.6 parts by mass Photopolymerization initiator (Irgacure OXE01, manufactured by BASF) ... 0.4 parts by mass Surfactant 101 ... 4.2 parts by mass Ultraviolet absorber (UV-503, manufactured by Daito Kagaku Co., Ltd.) ... 0.3 parts by mass PGMEA ... 42.6 parts by mass
- the materials used for the red colored composition and the yellow colored composition are as follows.
- Surfactant 101 1% by mass PGMEA solution of a compound having the following structure (weight average molecular weight: 14,000). In the following formulas, % indicating the ratio of repeating units is mol %.
- Example 1002 A color filter was formed in the same manner as in Example 1001 except that the red colored composition of Example 1001 was changed to the following magenta colored composition to form magenta pixels.
- the obtained color filter was incorporated into a solid-state imaging device according to a known method. This solid-state imaging device had a favorable image recognition ability.
- magenta colored composition After mixing and stirring the following components, the mixture was filtered through a nylon filter (manufactured by Nippon Pall Co., Ltd.) having a pore size of 0.45 ⁇ m to prepare a magenta colored composition.
- Magenta pigment dispersion ...44.9 parts by mass Resin 101...2.1 parts by mass Polymerizable compound (KAYARAD DPHA, manufactured by Nippon Kayaku Co., Ltd.)...1.5 parts by mass Polymerizable compound ( NK Ester A-DPH-12E, manufactured by Shin-Nakamura Chemical Co., Ltd.) ... 0.7 parts by mass Photopolymerization initiator (Irgacure OXE01, manufactured by BASF) ... 0.8 parts by mass Surfactant 101 ⁇ 4.2 parts by mass Ultraviolet absorber (UV-503, manufactured by Daito Kagaku Co., Ltd.) 0.3 parts by mass PGMEA 45.8 parts by mass
- ⁇ Magenta color pigment dispersion liquid 1 C I. Pigment Red 122 of 12.1 parts by mass, a dispersing agent (Disperbyk-161, manufactured by BYK-Chemie) of 5.5 parts by mass, and PGMEA of 82.4 parts by mass. ) for 3 hours to prepare a pigment dispersion.
- a high-pressure disperser NANO-3000-10 manufactured by Nippon BEE Co., Ltd.
- dispersion treatment was carried out under a pressure of 2000 kg/cm 3 and a flow rate of 500 g/min. This dispersion treatment was repeated 10 times to obtain a magenta pigment dispersion.
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Abstract
Description
上記着色剤は、無置換の銅フタロシアニン顔料と、ハロゲン化銅フタロシアニン顔料とを含み、
上記着色剤の全質量中における上記無置換の銅フタロシアニン顔料の含有量が10質量%以上であり、上記ハロゲン化銅フタロシアニン顔料の含有量が40質量%以上である、着色組成物。
<2> 上記無置換の銅フタロシアニン顔料は、カラーインデックスピグメントブルー15:4を含み、
上記ハロゲン化銅フタロシアニン顔料は、カラーインデックスピグメントグリーン7を含む、<1>に記載の着色組成物。
<3> 上記着色剤の全質量中における上記無置換の銅フタロシアニン顔料と上記ハロゲン化銅フタロシアニン顔料との合計の含有量が70~100質量%である、<1>または<2>に記載の着色組成物。
<4> 上記着色組成物を用いて膜厚が0.6μmの膜を形成した際に、上記膜の厚み方向における波長400~450nmの範囲の光の透過率の平均値が75%以上であり、上記膜の厚み方向における波長650~700nmの範囲の光の透過率の平均値が30%以下であり、透過率が50%を示す波長が波長560~590nmの範囲に存在する、<1>~<3>のいずれか1つに記載の着色組成物。
<5> 着色剤と、樹脂と、重合性化合物と、光重合開始剤と、紫外線吸収剤と、溶剤とを含む着色組成物であって、
上記着色組成物を用いて膜厚が0.6μmの膜を形成した際に、上記膜の厚み方向における波長400~450nmの範囲の光の透過率の平均値が75%以上であり、上記膜の厚み方向における波長650~700nmの範囲の光の透過率の平均値が30%以下であり、透過率が50%を示す波長が波長560~590nmの範囲に存在する、着色組成物。
<6> 上記着色組成物の全固形分中における上記紫外線吸収剤の含有量が0.5質量%以上である、<1>~<5>のいずれか1つに記載の着色組成物。
<7> 上記紫外線吸収剤は、波長365nmにおける吸光度A1に対する波長410nmにおける吸光度A2の比の値が0.06以下である、<1>~<6>のいずれか1つに記載の着色組成物。
<8> 上記紫外線吸収剤は、共役ジエン化合物、ベンゾトリアゾール化合物、ジベンゾイル化合物およびトリアジン化合物から選ばれる少なくとも1種である、<1>~<7>のいずれか1つに記載の着色組成物。
<9> 上記着色剤の100質量部に対して、上記樹脂を100~350質量部含む、<1>~<8>のいずれか1つに記載の着色組成物。
<10> 上記樹脂は、式(1)で表される繰り返し単位および式(2)で表される繰り返し単位から選ばれる少なくとも1種の繰り返し単位を有する樹脂を含む、<1>~<9>のいずれか1つに記載の着色組成物;
<11> 上記着色剤の全質量中におけるカラーインデックスピグメントブルー15:4の含有量が10~50質量%であり、
上記着色組成物の全固形分中における上記光重合開始剤の含有量が3~10質量%であり、
上記着色組成物の全固形分中における上記紫外線吸収剤の含有量が1~10質量%である、<1>~<10>のいずれか1つに記載の着色組成物。
<12> <1>~<11>のいずれか1つに記載の着色組成物から得られる膜。
<13> <12>に記載の膜を有するカラーフィルタ。
<14> <12>に記載の膜を有する固体撮像素子。
本明細書において、「~」とはその前後に記載される数値を下限値および上限値として含む意味で使用される。
本明細書における基(原子団)の表記において、置換および無置換を記していない表記は、置換基を有さない基(原子団)と共に置換基を有する基(原子団)をも包含する。例えば、「アルキル基」とは、置換基を有さないアルキル基(無置換アルキル基)のみならず、置換基を有するアルキル基(置換アルキル基)をも包含する。
本明細書において「露光」とは、特に断らない限り、光を用いた露光のみならず、電子線、イオンビーム等の粒子線を用いた描画も露光に含める。また、露光に用いられる光としては、水銀灯の輝線スペクトル、エキシマレーザに代表される遠紫外線、極紫外線(EUV光)、X線、電子線等の活性光線または放射線が挙げられる。
本明細書において、「(メタ)アクリレート」は、アクリレートおよびメタクリレートの双方、または、いずれかを表し、「(メタ)アクリル」は、アクリルおよびメタクリルの双方、または、いずれかを表し、「(メタ)アクリロイル」は、アクリロイルおよびメタクリロイルの双方、または、いずれかを表す。
本明細書において、構造式中のMeはメチル基を表し、Etはエチル基を表し、Buはブチル基を表し、Phはフェニル基を表す。
本明細書において、重量平均分子量および数平均分子量は、GPC(ゲルパーミエーションクロマトグラフィ)法により測定したポリスチレン換算値である。
本明細書において、全固形分とは、組成物の全成分から溶剤を除いた成分の総質量をいう。
本明細書において、顔料とは、溶剤に対して溶解しにくい着色剤を意味する。
本明細書において「工程」との語は、独立した工程だけではなく、他の工程と明確に区別できない場合であってもその工程の所期の作用が達成されれば、本用語に含まれる。
本発明の着色組成物の第1の態様は、着色剤と、樹脂と、重合性化合物と、光重合開始剤と、紫外線吸収剤と、溶剤とを含む着色組成物であって、上記着色剤は、無置換の銅フタロシアニン顔料と、ハロゲン化銅フタロシアニン顔料とを含み、上記着色剤の全質量中における無置換の銅フタロシアニン顔料の含有量が10質量%以上であり、ハロゲン化銅フタロシアニン顔料の含有量が40質量%以上であることを特徴とする。
また、本発明の着色組成物を用いて膜厚が0.6μmの膜を形成した際に、膜の厚み方向における波長650~700nmの範囲の光の透過率の平均値が25%以下であることが好ましく、20%以下であることがより好ましい。
また、本発明の着色組成物を用いて膜厚が0.6μmの膜を形成した際に、透過率が50%を示す波長が波長565~585nmの範囲に存在することが好ましく、570~580nmの範囲に存在することがより好ましい。
このような分光特性を有する着色組成物は、シアン色の画素形成用の着色組成物として好ましく用いられる。
本発明の着色組成物は着色剤を含有する。本発明の着色組成物に含まれる着色剤は、無置換の銅フタロシアニン顔料と、ハロゲン化銅フタロシアニン顔料とを含むものであることが好ましい。
態様1:ハロゲン化銅フタロシアニン顔料がC.I.ピグメントグリーン7のみである態様
態様2:ハロゲン化銅フタロシアニン顔料がC.I.ピグメントグリーン7とC.I.ピグメントグリーン36とを含む態様
C.I.ピグメントオレンジ2,5,13,16,17:1,31,34,36,38,43,46,48,49,51,52,55,59,60,61,62,64,71,73等(以上、オレンジ色顔料)、
C.I.ピグメントレッド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等(以上、赤色顔料)、
C.I.ピグメントグリーン58,59,62,63,64,65,66等(以上、緑色顔料)、
C.I.ピグメントバイオレット1,19,23,27,32,37,42,60,61等(以上、紫色顔料)、
C.I.ピグメントブルー1,2,16,22,29,60,64,66,79,80,87,88等(以上、青色顔料)。
また、着色剤の全質量中におけるハロゲン化銅フタロシアニン顔料の含有量は40質量%以上であることが好ましく、45質量%以上であることがより好ましく、50質量%以上であることが更に好ましい。上限は、85質量%以下であることが好ましく、75質量%以下であることがより好ましく、65質量%以下であることが更に好ましい。
また、着色剤の全質量中における無置換の銅フタロシアニン顔料とハロゲン化銅フタロシアニン顔料との合計の含有量は70~100質量%であることが好ましく、80~100質量%であることがより好ましく、85~100質量%であることが更に好ましい。
また、着色剤中における無置換の銅フタロシアニン顔料とハロゲン化銅フタロシアニン顔料との割合は、無置換の銅フタロシアニン顔料100質量部に対して、ハロゲン化銅フタロシアニン顔料が120~600質量部であることが好ましく、140~400質量部であることがより好ましく、160~200質量部であることが更に好ましい。
また、着色剤の全質量中におけるC.I.ピグメントグリーン7の含有量は40質量%以上であることが好ましく、45質量%以上であることがより好ましく、50質量%以上であることが更に好ましい。上限は、80質量%以下であることが好ましく、70質量%以下であることがより好ましく、62質量%以下であることが更に好ましい。
また、着色剤の全質量中におけるC.I.ピグメントブルー15:4とC.I.ピグメントグリーン7との合計の含有量は75~100質量%であることが好ましく、80~100質量%であることがより好ましく、85~100質量%であることが更に好ましい。
また、着色剤中におけるC.I.ピグメントブルー15:4とC.I.ピグメントグリーン7との割合は、C.I.ピグメントブルー15:4の100質量部に対して、C.I.ピグメントグリーン7が120~500質量部であることが好ましく、140~400質量部であることがより好ましく、160~300質量部であることが更に好ましい。
本発明の着色組成物は樹脂を含む。樹脂は、例えば、顔料などを着色組成物中で分散させる用途や、バインダーの用途で配合される。なお、主に顔料などを着色組成物中で分散させるために用いられる樹脂を分散剤ともいう。ただし、樹脂のこのような用途は一例であって、このような用途以外を目的として樹脂を使用することもできる。
両方の繰り返し単位を含む場合、式(1)で表される繰り返し単位と式(2)で表される繰り返し単位との比率は、モル比で、式(1)で表される繰り返し単位:式(2)で表される繰り返し単位=5:95~95:5であることが好ましく、10:90~90:10であることがより好ましく、20:80~80:20であることが更に好ましい。
式(Y2):-C(=O)OC(RY4)(RY5)(RY6)
式(Y3):-C(RY7)(RY8)(ORY9)
式(Y4):-C(RY10)(H)(ArY1)
式(Y5):-C(=O)(RY11)
式(Y2)中、RY4~RY6は、各々独立にアルキル基を表し、RY4~RY6のうちの2つが結合して環を形成していてもよい;
式(Y3)中、RY7およびRY8は、各々独立に、水素原子、アルキル基またはアリール基を表し、RY7およびRY8の少なくとも一方がアルキル基またはアリール基であり、RY9は、アルキル基またはアリール基を表し、RY7またはRY8と、RY9とが結合して環を形成していてもよい;
式(Y4)中、ArY1は、アリール基を表し、RY10は、アルキル基またはアリール基を表す;
式(Y5)中、RY11は、アルキル基またはアリール基を表す。
アルキル基は、直鎖状、分岐状、環状のいずれでもよい。アルキル基の炭素数は1~12であることが好ましく、1~6であることがより好ましく、1~4であることがさらに好ましい。アリール基の炭素数は6~20が好ましく、6~12がより好ましい。RY7またはRY8と、RY9とが結合して形成される環としては、テトラヒドロフラニル基、テトラヒドロピラニル基等が挙げられる。式(Y3)において、RY7またはRY8と、RY9とが結合して環を形成していることが好ましい。また、RY7およびRY8の一方は水素原子であることが好ましい。
式(B2)において、Xb2は3価の連結基を表し、Lb2は単結合または2価の連結基を表し、Zb2は酸基が保護基で保護された基を表す。
式(B3)において、Xb3は3価の連結基を表し、Lb3は単結合または2価の連結基を表し、Zb3はエチレン性不飽和結合含有基を表す。
式(Ac-2)中、Ar10は芳香族カルボキシ基を含む基を表し、L11は、-COO-または-CONH-を表し、L12は3価の連結基を表し、P10はポリマー鎖を表す。
式(Ar-12)中、n2は1~8の整数を表し、1~4の整数であることが好ましく、1または2であることがより好ましく、2であることが更に好ましい。
式(Ar-13)中、n3およびn4はそれぞれ独立して0~4の整数を表し、0~2の整数であることが好ましく、1または2であることがより好ましく、1であることが更に好ましい。ただし、n3およびn4の少なくとも一方は1以上の整数である。
式(Ar-13)中、Q1は、単結合、-O-、-CO-、-COOCH2CH2OCO-、-SO2-、-C(CF3)2-、上記式(Q-1)で表される基または上記式(Q-2)で表される基を表す。
式(Ar-11)~(Ar-13)中、*1はL1との結合位置を表す。
また、本発明の着色組成物は、着色剤の100質量部に対して、樹脂を100~350質量部含むことが好ましく、樹脂を120~300質量部含むことがより好ましく、樹脂を140~250質量部含むことが更に好ましい。
また、樹脂中における上述した式(1)で表される繰り返し単位および式(2)で表される繰り返し単位から選ばれる少なくとも1種の繰り返し単位を有する樹脂の含有量は、10質量%以上であることが好ましく、20質量%以上であることがより好ましく、30質量%以上であることが更に好ましい。上限は100質量%以下であってもよく、90質量%以下であってもよく、80質量%以下であってもよい。
本発明の着色組成物は、樹脂を1種のみ含んでいてもよいし、2種以上含んでいてもよい。樹脂を2種以上含む場合は、それらの合計量が上記範囲となることが好ましい。
本発明の着色組成物は、重合性化合物を含有する。重合性化合物としては、エチレン性不飽和結合含有基を有する化合物などが挙げられる。エチレン性不飽和結合含有基としては、ビニル基、(メタ)アリル基、(メタ)アクリロイル基などが挙げられる。本発明で用いられる重合性化合物は、ラジカル重合性化合物であることが好ましい。
式(Z-5)中、nは、0~6の整数が好ましく、0~4の整数がより好ましい。また、各nの合計は、3~60の整数が好ましく、3~24の整数がより好ましく、6~12の整数が特に好ましい。
また、式(Z-4)又は式(Z-5)中のE、すなわち-((CH2)yCH2O)-又は-((CH2)yCH(CH3)O)-は、酸素原子側の末端がXに結合する形態が好ましい。
また、着色組成物は樹脂100質量部に対して重合性化合物を20~200質量部含有することが好ましい。上限は、150質量部以下であることが好ましく、100質量部以下であることがより好ましい。下限は、30質量部以上であることが好ましく、40質量部以上であることがより好ましい。
本発明の着色組成物は、重合性化合物を、1種のみ含んでいてもよいし、2種以上含んでいてもよい。重合性化合物を2種以上含む場合は、それらの合計量が上記範囲となることが好ましい。
本発明の着色組成物は光重合開始剤を含有する。光重合開始剤としては、特に制限はなく、公知の光重合開始剤の中から適宜選択することができる。例えば、紫外線領域から可視領域の光線に対して感光性を有する化合物が好ましい。光重合開始剤は、光ラジカル重合開始剤であることが好ましい。
RX2は、アルキル基、アルケニル基、アルコキシ基、アリール基、アリールオキシ基、ヘテロ環基、ヘテロ環オキシ基、アルキルスルファニル基、アリールスルファニル基、アルキルスルフィニル基、アリールスルフィニル基、アルキルスルホニル基、アリールスルホニル基、アシルオキシ基またはアミノ基を表す。
RX3~RX14は、それぞれ独立して水素原子または置換基を表す。ただし、RX10~RX14のうち少なくとも一つは、電子求引性基である。
また、着色組成物は、重合性化合物100質量部に対して光重合開始剤を15~100質量部含有することが好ましい。上限は、80質量部以下であることが好ましく、70質量部以下であることがより好ましい。下限は、25質量部以上であることが好ましく、33質量部以上であることがより好ましい。
本発明の着色組成物において、光重合開始剤は1種のみを用いてもよく、2種以上を用いてもよい。2種以上を用いる場合は、それらの合計量が上記範囲となることが好ましい。
本発明の着色組成物は、紫外線吸収剤を含有する。本明細書における紫外線吸収剤とは、紫外線吸収機能を有する有機化合物のことであって、紫外線の照射により効率的にラジカルなどの活性種を発生する光重合開始剤とは異なる化合物のことを意味する。紫外線吸収剤は、紫外線を吸収し、熱エネルギ-などに変換して発散する作用を有する化合物であることが好ましい。また、紫外線吸収剤は、紫外線に対して安定な化合物であることが好ましい。すなわち、紫外線吸収剤は、紫外線照射によって、分解、酸化、還元などの反応による分子の破断がされにくい化合物であることが好ましい。
式中、Rd2~Rd9は、それぞれ独立に水素原子、ハロゲン原子、ヒドロキシ基、炭素数1~15のアルキル基、炭素数3~8のアルケニル基又は炭素数6~18のアリール基、炭素数7~18のアルキルアリール基または炭素数7~18のアリールアルキル基を表す。アルキル基、アルケニル基、アリール基、アルキルアリール基およびアリールアルキル基は、置換基を有していてもよい。置換基としては、以下に示す置換基Tiで説明した基が挙げられる。
炭化水素基としては、アルキル基、アルケニル基、アルキニル基、アリール基が挙げられる。アルキル基の炭素数は、1~30が好ましく、1~15がより好ましく、1~8が更に好ましい。アルキル基は、直鎖、分岐、環状のいずれでもよく、直鎖または分岐が好ましく、分岐がより好ましい。
アルケニル基の炭素数は、2~30が好ましく、2~12がより好ましく、2~8が特に好ましい。アルケニル基は直鎖、分岐、環状のいずれでもよく、直鎖または分岐が好ましい。
アルキニル基の炭素数は、2~30が好ましく、2~25がより好ましい。アルキニル基は直鎖、分岐、環状のいずれでもよく、直鎖または分岐が好ましい。
アリール基の炭素数は、6~30が好ましく、6~20がより好ましく、6~12が更に好ましい。
複素環基は、単環であってもよく、縮合環であってもよい。複素環基は、単環または縮合数が2~4の縮合環が好ましい。複素環基の環を構成するヘテロ原子の数は1~3が好ましい。複素環基の環を構成するヘテロ原子は、窒素原子、酸素原子または硫黄原子が好ましい。複素環基の環を構成する炭素原子の数は3~30が好ましく、3~18がより好ましく、3~12がより好ましい。
炭化水素基および複素環基は、置換基を有していてもよく、無置換であってもよい。置換基としては、上述した置換基Tiで説明した置換基が挙げられる。
また、着色組成物は、光重合開始剤の100質量部に対して、紫外線吸収剤を10~100質量部含有することが好ましい。上限は、90質量部以下であることが好ましく、80質量部以下であることがより好ましい。下限は、20質量部以上であることが好ましく、30質量部以上であることがより好ましい。紫外線吸収剤と光重合開始剤との割合が上記範囲であれば、線幅感度の照度依存性の改善と着色組成物の経時安定性を高い水準で両立できる。
また、着色組成物は、重合性化合物の100質量部に対して、紫外線吸収剤を5~50質量部含有することが好ましい。上限は、40質量部以下であることが好ましく、30質量部以下であることがより好ましい。下限は、7質量部以上であることが好ましく、10質量部以上であることがより好ましい。紫外線吸収剤と重合性化合物との割合が上記範囲であれば、線幅感度の照度依存性の改善に効果的である。
紫外線吸収剤は1種単独であってもよいし、2種以上を併用してもよい。2種以上を併用する場合は、それらの合計が上記範囲である。
本発明の着色組成物は、溶剤を含有する。溶剤としては、有機溶剤が挙げられる。溶剤の種類は、各成分の溶解性や組成物の塗布性を満足すれば基本的には特に制限はない。有機溶剤としては、エステル系溶剤、ケトン系溶剤、アルコール系溶剤、アミド系溶剤、エーテル系溶剤、炭化水素系溶剤などが挙げられる。これらの詳細については、国際公開第2015/166779号の段落番号0223を参酌でき、この内容は本明細書に組み込まれる。また、環状アルキル基が置換したエステル系溶剤、環状アルキル基が置換したケトン系溶剤も好ましく用いることもできる。有機溶剤の具体例としては、ポリエチレングリコールモノメチルエーテル、ジクロロメタン、3-エトキシプロピオン酸メチル、3-エトキシプロピオン酸エチル、エチルセロソルブアセテート、乳酸エチル、ジエチレングリコールジメチルエーテル、酢酸ブチル、3-メトキシプロピオン酸メチル、2-ヘプタノン、2-ペンタノン、3-ペンタノン、4-ヘプタノン、シクロヘキサノン、2-メチルシクロヘキサノン、3-メチルシクロヘキサノン、4-メチルシクロヘキサノン、シクロヘプタノン、シクロオクタノン、酢酸シクロヘキシル、シクロペンタノン、エチルカルビトールアセテート、ブチルカルビトールアセテート、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、3-メトキシ-N,N-ジメチルプロパンアミド、3-ブトキシ-N,N-ジメチルプロパンアミド、プロピレングリコールジアセテート、3-メトキシブタノール、メチルエチルケトン、ガンマブチロラクトン、スルホラン、アニソール、1,4-ジアセトキシブタン、ジエチレングリコールモノエチルエーテルアセタート、二酢酸ブタン-1,3-ジイル、ジプロピレングリコールメチルエーテルアセタート、ジアセトンアルコール(別名としてダイアセトンアルコール、4-ヒドロキシ-4-メチル-2-ペンタノン)、2-メトキシプロピルアセテート、2-メトキシ-1-プロパノール、イソプロピルアルコールなどが挙げられる。ただし有機溶剤としての芳香族炭化水素類(ベンゼン、トルエン、キシレン、エチルベンゼン等)は、環境面等の理由により低減したほうがよい場合がある(例えば、有機溶剤全量に対して、50質量ppm(parts per million)以下とすることもでき、10質量ppm以下とすることもでき、1質量ppm以下とすることもできる)。
本発明の着色組成物は、顔料誘導体を含有することができる。顔料誘導体は例えば分散助剤として用いられる。顔料誘導体としては、色素骨格に酸基または塩基性基が結合した構造を有する化合物が挙げられる。
本発明の着色組成物は、ポリアルキレンイミンを含有することもできる。ポリアルキレンイミンは例えば顔料の分散助剤として用いられる。分散助剤とは、着色組成物中において顔料の分散性を高めるための素材のことである。ポリアルキレンイミンとは、アルキレンイミンを開環重合したポリマーのことである。ポリアルキレンイミンは、1級アミノ基と、2級アミノ基と、3級アミノ基とをそれぞれ含む分岐構造を有するポリマーである。アルキレンイミンの炭素数は2~6が好ましく、2~4がより好ましく、2または3であることが更に好ましく、2であることが特に好ましい。
本発明の着色組成物は、硬化促進剤を含有することができる。硬化促進剤としては、チオール化合物、メチロール化合物、アミン化合物、ホスホニウム塩化合物、アミジン塩化合物、アミド化合物、塩基発生剤、イソシアネート化合物、アルコキシシラン化合物、オニウム塩化合物などが挙げられる。硬化促進剤の具体例としては、国際公開第2018/056189号の段落番号0094~0097に記載の化合物、特開2015-034963号公報の段落番号0246~0253に記載の化合物、特開2013-041165号公報の段落番号0186~0251に記載の化合物、特開2014-055114号公報に記載のイオン性化合物、特開2012-150180号公報の段落番号0071~0080に記載の化合物、特開2011-253054号公報に記載のエポキシ基を有するアルコキシシラン化合物、特許第5765059号公報の段落番号0085~0092に記載の化合物、特開2017-036379号公報に記載のカルボキシ基含有エポキシ硬化剤などが挙げられる。着色組成物の全固形分中における硬化促進剤の含有量は0.3~8.9質量%であることが好ましく、0.8~6.4質量%であることがより好ましい。
本発明の着色組成物は、重合禁止剤を含有することができる。重合禁止剤としては、ハイドロキノン、p-メトキシフェノール、ジ-tert-ブチル-p-クレゾール、ピロガロール、tert-ブチルカテコール、ベンゾキノン、4,4’-チオビス(3-メチル-6-tert-ブチルフェノール)、2,2’-メチレンビス(4-メチル-6-t-ブチルフェノール)、N-ニトロソフェニルヒドロキシアミン塩(アンモニウム塩、第一セリウム塩等)が挙げられる。中でも、p-メトキシフェノールが好ましい。着色組成物の全固形分中における重合禁止剤の含有量は、0.0001~5質量%であることが好ましい。重合禁止剤は、1種類のみでもよく、2種類以上でもよい。2種類以上の場合は、合計量が上記範囲となることが好ましい。
本発明の着色組成物は、シランカップリング剤を含有することができる。本発明において、シランカップリング剤は、加水分解性基とそれ以外の官能基とを有するシラン化合物を意味する。また、加水分解性基とは、ケイ素原子に直結し、加水分解反応及び縮合反応の少なくともいずれかによってシロキサン結合を生じ得る置換基をいう。加水分解性基としては、例えば、ハロゲン原子、アルコキシ基、アシルオキシ基などが挙げられ、アルコキシ基が好ましい。すなわち、シランカップリング剤は、アルコキシシリル基を有する化合物が好ましい。また、加水分解性基以外の官能基としては、例えば、ビニル基、(メタ)アリル基、(メタ)アクリロイル基、メルカプト基、エポキシ基、オキセタニル基、アミノ基、ウレイド基、スルフィド基、イソシアネート基、フェニル基などが挙げられ、アミノ基、(メタ)アクリロイル基およびエポキシ基が好ましい。シランカップリング剤の具体例としては、N-β-アミノエチル-γ-アミノプロピルメチルジメトキシシラン(信越化学工業(株)製、商品名 KBM-602)、N-β-アミノエチル-γ-アミノプロピルトリメトキシシラン(信越化学工業(株)製、商品名 KBM-603)、N-β-アミノエチル-γ-アミノプロピルトリエトキシシラン(信越化学工業(株)製、商品名 KBE-602)、γ-アミノプロピルトリメトキシシラン(信越化学工業(株)製、商品名 KBM-903)、γ-アミノプロピルトリエトキシシラン(信越化学工業(株)製、商品名 KBE-903)、3-メタクリロキシプロピルメチルジメトキシシラン(信越化学工業(株)製、商品名 KBM-502)、3-メタクリロキシプロピルトリメトキシシラン(信越化学工業(株)製、商品名 KBM-503)等がある。また、シランカップリング剤の具体例については、特開2009-288703号公報の段落番号0018~0036に記載の化合物、特開2009-242604号公報の段落番号0056~0066に記載の化合物が挙げられ、これらの内容は本明細書に組み込まれる。着色組成物の全固形分中におけるシランカップリング剤の含有量は、0.01~15.0質量%であることが好ましく、0.05~10.0質量%であることがより好ましい。シランカップリング剤は、1種類のみでもよく、2種類以上でもよい。2種類以上の場合は、合計量が上記範囲となることが好ましい。
本発明の着色組成物は、界面活性剤を含有することができる。界面活性剤としては、フッ素系界面活性剤、ノニオン系界面活性剤、カチオン系界面活性剤、アニオン系界面活性剤、シリコーン系界面活性剤などの各種界面活性剤を使用することができる。界面活性剤はシリコーン系界面活性剤またはフッ素系界面活性剤であることが好ましい。界面活性剤については、国際公開第2015/166779号の段落番号0238~0245に記載された界面活性剤を参照することができ、この内容は本明細書に組み込まれる。
本発明の着色組成物は、酸化防止剤を含有することができる。酸化防止剤としては、フェノール化合物、亜リン酸エステル化合物、チオエーテル化合物などが挙げられる。フェノール化合物としては、フェノール系酸化防止剤として知られる任意のフェノール化合物を使用することができる。好ましいフェノール化合物としては、ヒンダードフェノール化合物が挙げられる。フェノール性ヒドロキシ基に隣接する部位(オルト位)に置換基を有する化合物が好ましい。前述の置換基としては炭素数1~22の置換又は無置換のアルキル基が好ましい。また、酸化防止剤は、同一分子内にフェノール基と亜リン酸エステル基を有する化合物も好ましい。また、酸化防止剤は、リン系酸化防止剤も好適に使用することができる。リン系酸化防止剤としてはトリス[2-[[2,4,8,10-テトラキス(1,1-ジメチルエチル)ジベンゾ[d,f][1,3,2]ジオキサホスフェピン-6-イル]オキシ]エチル]アミン、トリス[2-[(4,6,9,11-テトラ-tert-ブチルジベンゾ[d,f][1,3,2]ジオキサホスフェピン-2-イル)オキシ]エチル]アミン、亜リン酸エチルビス(2,4-ジ-tert-ブチル-6-メチルフェニル)などが挙げられる。酸化防止剤の市販品としては、例えば、アデカスタブ AO-20、アデカスタブ AO-30、アデカスタブ AO-40、アデカスタブ AO-50、アデカスタブ AO-50F、アデカスタブ AO-60、アデカスタブ AO-60G、アデカスタブ AO-80、アデカスタブ AO-330(以上、(株)ADEKA製)などが挙げられる。また、酸化防止剤は、特許第6268967号公報の段落番号0023~0048に記載された化合物、国際公開第2017/006600号に記載された化合物、国際公開第2017/164024号に記載された化合物、韓国公開特許第10-2019-0059371号公報に記載された化合物を使用することもできる。着色組成物の全固形分中における酸化防止剤の含有量は、0.01~20質量%であることが好ましく、0.3~15質量%であることがより好ましい。酸化防止剤は1種のみを用いてもよく、2種以上を用いてもよい。2種以上を用いる場合は、合計量が上記範囲となることが好ましい。
本発明の着色組成物は、必要に応じて、増感剤、硬化促進剤、フィラー、熱硬化促進剤、可塑剤及びその他の助剤類(例えば、導電性粒子、消泡剤、難燃剤、レベリング剤、剥離促進剤、香料、表面張力調整剤、連鎖移動剤など)を含有してもよい。これらの成分を適宜含有させることにより、膜物性などの性質を調整することができる。これらの成分は、例えば、特開2012-003225号公報の段落番号0183以降(対応する米国特許出願公開第2013/0034812号明細書の段落番号0237)の記載、特開2008-250074号公報の段落番号0101~0104、0107~0109等の記載を参酌でき、これらの内容は本明細書に組み込まれる。また、本発明の着色組成物は、必要に応じて、潜在酸化防止剤を含有してもよい。潜在酸化防止剤としては、酸化防止剤として機能する部位が保護基で保護された化合物であって、100~250℃で加熱するか、又は酸/塩基触媒存在下で80~200℃で加熱することにより保護基が脱離して酸化防止剤として機能する化合物が挙げられる。潜在酸化防止剤としては、国際公開第2014/021023号、国際公開第2017/030005号、特開2017-008219号公報に記載された化合物が挙げられる。潜在酸化防止剤の市販品としては、アデカアークルズGPA-5001((株)ADEKA製)等が挙げられる。
着色組成物の収容容器としては、特に限定はなく、公知の収容容器を用いることができる。また、収容容器として、原材料や着色組成物中への不純物混入を抑制することを目的に、容器内壁を6種6層の樹脂で構成する多層ボトルや6種の樹脂を7層構造にしたボトルを使用することも好ましい。このような容器としては例えば特開2015-123351号公報に記載の容器が挙げられる。また、容器内壁は、容器内壁からの金属溶出を防ぎ、着色組成物の保存安定性を高めたり、成分変質を抑制するなど目的で、ガラス製やステンレス製などにすることも好ましい。
本発明の着色組成物は、前述の成分を混合して調製できる。着色組成物の調製に際しては、全成分を同時に溶剤に溶解および/または分散して着色組成物を調製してもよいし、必要に応じて、各成分を適宜2つ以上の溶液または分散液としておいて、使用時(塗布時)にこれらを混合して着色組成物を調製してもよい。
本発明の膜は、上述した本発明の着色組成物から得られる膜である。本発明の膜は、カラーフィルタなどに用いることができる。具体的には、カラーフィルタの着色層(画素)として好ましく用いることができ、シアン色画素としてより好ましく用いられる。本発明の膜の膜厚は、目的に応じて適宜調整できるが、0.1~20μmであることが好ましい。膜厚の上限は10μm以下であることが好ましく、5μm以下であることがより好ましく、3μm以下であることが更に好ましく、1.5μm以下であることが特に好ましい。膜厚の下限は、0.2μm以上が好ましく、0.3μm以上がより好ましい。
また、本発明の膜は、波長650~700nmの範囲の光の透過率の平均値が30%以下であることが好ましく、25%以下であることがより好ましく、20%以下であることが更に好ましい。下限は0%以上とすることができる。
また、本発明の膜は、透過率が50%を示す光の波長が、波長560~590nmの範囲に存在することが好ましく、波長565~585nmの範囲に存在することがより好ましく、波長570~580nmの範囲に存在することが更に好ましい。
画素の形成方法について説明する。本発明の着色組成物を用いることで、例えば、シアン色画素を形成することができる。
本発明のカラーフィルタは、上述した本発明の膜を有する。好ましくは、カラーフィルタの着色画素として、より好ましくはシアン色画素として、本発明の膜を有する。本発明のカラーフィルタは、固体撮像素子や画像表示装置などに用いることができる。
本発明の固体撮像素子は、上述した本発明の膜を有する。固体撮像素子の構成としては、本発明の膜を備え、固体撮像素子として機能する構成であれば特に限定はないが、例えば、以下のような構成が挙げられる。
本発明の膜は画像表示装置に用いることもできる。画像表示装置としては、液晶表示装置や有機エレクトロルミネッセンス表示装置などが挙げられる。画像表示装置の定義や各画像表示装置の詳細については、例えば「電子ディスプレイデバイス(佐々木昭夫著、(株)工業調査会、1990年発行)」、「ディスプレイデバイス(伊吹順章著、産業図書
(株)平成元年発行)」などに記載されている。また、液晶表示装置については、例えば「次世代液晶ディスプレイ技術(内田龍男編集、(株)工業調査会、1994年発行)」に記載されている。本発明が適用できる液晶表示装置に特に制限はなく、例えば、上記の「次世代液晶ディスプレイ技術」に記載されている色々な方式の液晶表示装置に適用できる。
下記表に記載の素材を混合した混合液を、ビーズミル(ジルコニアビーズ0.1mm径)を用いて3時間混合および分散した。次いで、減圧機構付き高圧分散機NANO-3000-10(日本ビーイーイー(株)製)を用いて圧力2000kg/cm3および流量500g/minの条件の下、分散処理を行なった。この分散処理を全10回繰り返して、分散液を得た。なお、以下の表において、配合量の欄に記載の数値の単位は質量部である。
PG7 : C.I.ピグメントグリーン36(ハロゲン化銅フタロシアニン顔料)
PG36 : C.I.ピグメントグリーン36(ハロゲン化銅フタロシアニン顔料)
PB15:4 : C.I.ピグメントブルー15:4(無置換の銅フタロシアニン顔料)
PB15:6 : C.I.ピグメントブルー15:6(無置換の銅フタロシアニン顔料)
還流冷却器、滴下ロート及び撹拌機を備えたフラスコ内に窒素を適量流し、窒素雰囲気に置換し、プロピレングリコールモノメチルエーテルアセテート(PGMEA)の340質量部を入れ、撹拌しながら80℃まで加熱した。次いで、アクリル酸の57質量部、3,4-エポキシトリシクロ[5.2.1.02,6]デカン-8-イルアクリレート及び3,4-エポキシトリシクロ[5.2.1.02,6]デカン-9-イルアクリレートの混合物(含有比はモル比で1:1)の54質量部、ベンジルメタクリレートの239質量部、PGMEAの73質量部の混合溶液を5時間かけて滴下した。次いで、重合開始剤(2,2-アゾビス(2,4-ジメチルバレロニトリル))の40質量部をPGMEAの197質量部に溶解した溶液を6時間かけて滴下した。重合開始剤溶液の滴下終了後、80℃で3時間保持した後、室温まで冷却して下記構造の樹脂を得た。得られた樹脂の重量平均分子量は9400、分散度は1.89、酸価は114mgKOH/gであった。
Z-1:プロピレングリコールモノメチルエーテルアセテート(PGMEA)
下記の表に記載の原料を混合して、着色組成物を製造した。なお、以下の表において、配合量の欄に記載の数値の単位は質量部である。
分散液1~9:上述した分散液1~9
還流冷却器、滴下ロート及び攪拌機を備えたフラスコ内に窒素を適量流し窒素雰囲気に置換し、PGMEAの371質量部を入れ、攪拌しながら85℃まで加熱した。次いで、アクリル酸の54質量部、3,4-エポキシトリシクロ[5.2.1.02,6]デカン-8と9-イルアクリレートの混合物の225質量部、ビニルトルエン(異性体混合物)の81質量部、PGMEAの80質量部の混合溶液を4時間かけて滴下した。一方、重合開始剤2,2-アゾビス(2,4-ジメチルバレロニトリル)の30質量部をPGMEAの160質量部に溶解した溶液を5時間かけて滴下した。開始剤溶液の滴下終了後、4時間85℃で保持した後、室温まで冷却して、樹脂を合成した。得られた樹脂の重量平均分子量は10600、分散度は2.01、酸価は43mgKOH/gであった。次いで、PGMEAを加えて固形分濃度を40質量%に調整し、バインダーB-2を得た。
D-1:下記構造の化合物の混合物(左側化合物(6官能の(メタ)アクリレート化合物)と右側化合物(5官能の(メタ)アクリレート化合物)とのモル比が7:3の混合物)
D-5:EBECRYL80(ダイセル・オルネクス社製、アミン含有4官能アクリレート)
D-6:エトキシ化ジペンタエリスリトールヘキサメタクリレート
E-1:下記構造の化合物(共役ジエン化合物)
E-3:Tinuvin 477(BASF製、トリアジン化合物)
E-4:Tinuvin P(BASF製、ベンゾトリアゾール化合物)
E-5:KEMISORB 10(ケミプロ化成(株)製、ベンゾフェノン化合物)
E-6:Sumisorb 200(住化ケムテックス(株)製、ベンゾトリアゾール化合物)
F-1:下記構造の化合物(シリコーン系界面活性剤、水酸基価62mgKOH/g)。
G-1:p-メトキシフェノール
H-1:下記構造の化合物(エポキシ基を有する化合物、重量平均分子量3500)
H-3:下記構造の化合物(シランカップリング剤)
H-5:アデカスタブ AO-80((株)ADEKA製、酸化防止剤)
Z-1:プロピレングリコールモノメチルエーテルアセテート(PGMEA)
Z-2:プロピレングリコールモノメチルエーテル(PGME)
Z-3:シクロペンタノン
Z-4:シクロヘキサノン
Z-5:アニソール
Z-6:ジアセトンアルコール
Z-7:シクロヘキサノールアセテート
ガラス基板上に着色組成物をスピンコート法で塗布し、次いで、ホットプレートを使用して100℃120秒加熱処理(プリベーク)し、次いでi線で1000mJ/cm2の露光量で露光し、次いで、200℃で5分間加熱を行い、厚さ0.6μmの膜を作製した。得られた膜について、分光器(大塚電子(株)製、MCPD-3000)を用い、波長400~700nmの範囲の光透過率(透過率)を測定し、波長400~450nmの範囲の光の透過率の平均値(T1)、波長650~700nmの範囲の光の透過率の平均値(T2)および、透過率が50%を示す波長(λ50)をそれぞれ求め、以下の基準で分光特性を評価した。
A:T1が85%以上である。
B:T1が80%以上85%未満である。
C:T1が75%以上80%未満である。
D:T1が75%未満である。
A:T2が20%以下である。
B:T2が20%を超え25%以下である。
C:T2が25%を超え30%以下である。
D:T2が30%を超える。
A:λ50が波長570nm以上580nm以下の範囲に存在する。
B:λ50が波長565nm以上570nm未満の範囲、または、波長580nmを超え585nm以下の範囲に存在する。
C:λ50が波長560nm以上565nm未満の範囲、または、波長585nmを超え590nm以下の範囲に存在する。
D:λ50が波長560nm未満の範囲、または、波長590nmを超える範囲に存在する。
シリコンウエハ上に着色組成物をスピンコート法で塗布し、次いで、ホットプレートを使用して100℃120秒加熱処理(プリベーク)し、厚さ0.6μmの組成物層を形成した。次いで、この組成物層に対して、一辺1.0μmの正方形状の非マスク部が4mm×3mmの領域に配列されたマスクを介して、i線ステッパー露光装置FPA-3000i5+(Canon(株)製)を使用して波長365nmの光を6000W/m2の露光照度、500mJ/cm2の露光量で照射して露光した。次いで、露光後の組成物層が形成されているシリコンウエハを、スピン・シャワー現像機(DW-30型、(株)ケミトロニクス製)の水平回転テーブル上に載置し、現像液(CD-2000、富士フイルムエレクトロニクスマテリアルズ(株)製)を用い、23℃で60秒間パドル現像した。次いで、シリコンウエハを回転数50rpmで回転させつつ、その回転中心の上方より純水を噴出ノズルからシャワー状に供給してリンス処理を行ない、その後スプレー乾燥してパターン(画素)を形成し、画素付き基板を製造した。次に、基板上の画素を分割し、断面を白金蒸着した後、走査型電子顕微鏡((株)日立ハイテク製)を用いて断面走査電子顕微鏡(SEM)像を得た。断面SEM像から5個の画素を抽出し、5個の画素の線幅の平均値を求めた。
露光時の露光照度を10000W/m2、20000W/m2または30000W/m2に変更した以外は上記と同様にして画素を形成し、画素付き基板を製造した。各基板上の画素を分割し、上記と同様にして断面SEM像を得て、各断面SEM像から、5個の画素を抽出して、5個の画素の線幅の平均値を求めた。
露光照度6000W/m2の条件で露光して作成した画素付き基板をA1、露光照度10000W/m2の条件で露光して作成した画素付き基板をA2、露光照度20000W/m2の条件で露光して作成した画素付き基板をA3、露光照度30000W/m2の条件で露光して作成した画素付き基板をA4とする。
A1~A4の画素の線幅の平均値の標準偏差σを求め、以下の基準で線幅の照度依存性を評価した。
A:標準偏差σが0.3μm未満である。
B:標準偏差σが0.3μm以上、0.5μm未満である。
C:標準偏差σが0.5μm以上、0.7μm未満である。
D:標準偏差σが0.7μm以上である。
シリコンウエハ上に着色組成物をスピンコート法で塗布し、次いで、ホットプレートを使用して100℃120秒加熱処理(プリベーク)し、厚さ0.6μmの組成物層を形成した。なお、着色組成物には、製造直後の着色組成物、または、5℃の恒温槽で12か月間保管後の着色組成物を用いた。また、各着色組成物は温度を23℃に調整して用いた。
次いで、この組成物層に対して、一辺1.0μmの正方形状の非マスク部が4mm×3mmの領域に配列されたマスクを介して、i線ステッパー露光装置FPA-3000i5+(Canon(株)製)を使用して波長365nmの光を10000W/m2の露光照度、500mJ/cm2の露光量で照射して露光した。次いで、露光後の組成物層が形成されているシリコンウエハを、スピン・シャワー現像機(DW-30型、(株)ケミトロニクス製)の水平回転テーブル上に載置し、現像液(CD-2000、富士フイルムエレクトロニクスマテリアルズ(株)製)を用い、23℃で60秒間パドル現像した。次いで、シリコンウエハを回転数50rpmで回転させつつ、その回転中心の上方より純水を噴出ノズルからシャワー状に供給してリンス処理を行ない、その後スプレー乾燥して画素を形成し、画素付き基板を製造した。次に、基板上の画素を分割し、断面を白金蒸着した後、走査型電子顕微鏡((株)日立ハイテク製)を用いて断面SEM像を得た。断面SEM像から5個の画素を抽出し、5個の画素の線幅の平均値を求めた。
以下の計算式から線幅の変化率を算出し、以下の基準で感度の経時安定性を評価した。
線幅の変化率(%)=((線幅の平均値2/線幅の平均値1)-1)×100
線幅の平均値1は、製造直後の着色組成物を用いて形成した画素の線幅の平均値であり、線幅の平均値2は、5℃の恒温槽で12か月間保管後の着色組成物を用いて形成した画素の線幅の平均値である。
A:線幅の変化率が5.0%未満
B:線幅の変化率が5.0%以上7.5%未満
C:線幅の変化率が7.5%以上10.0%未満
D:線幅の変化率が10.0%以上
ガラス基板上に着色組成物をスピンコート法で塗布し、次いで、ホットプレートを使用して100℃120秒加熱処理(プリベーク)し、次いでi線で1000mJ/cm2の露光量で露光し、次いで、200℃で5分間加熱を行い、厚さ0.6μmの膜を作製した。得られた膜について分光器(大塚電子(株)製、MCPD-3000)を用い、波長400~700nmの範囲の光透過率(透過率)を測定した。次に、上記で作製した膜に対し、耐光試験機(スーパーキセノンウェザーメーターSX75、スガ試験機株式会社製)を用いて100000Luxの光を2000時間かけて照射した(総照射量2億Lux・hr)。光照射後の膜の透過率を測定し、以下の基準にて耐光性を評価した。
A:光照射後の膜の波長400~700nmの透過率の積算値が、光照射前の膜の波長400~700nmの透過率の積算値の98%以上である。
B:光照射後の膜の波長400~700nmの透過率の積算値が、光照射前の膜の波長400~700nmの透過率の積算値の94%以上98%未満である。
C:光照射後の膜の波長400~700nmの透過率の積算値が、光照射前の膜の波長400~700nmの透過率の積算値の90%以上94%未満である。
D:光照射後の膜の波長400~700nmの透過率の積算値が、光照射前の膜の波長400~700nmの透過率の積算値の90%未満である。
シリコンウエハ上に、実施例1の着色組成物を製膜後の膜厚が0.6μmになるようにスピンコート法で塗布した。次いで、ホットプレートを用いて、100℃で2分間加熱した。次いで、i線ステッパー露光装置FPA-3000i5+(キヤノン(株)製)を用い、1000mJ/cm2の露光量で1μm四方のドットパターンのマスクを介して露光した。次いで、水酸化テトラメチルアンモニウム(TMAH)0.3質量%水溶液を用い、23℃で60秒間パドル現像を行った。その後、スピンシャワーにてリンスを行い、更に純水にて水洗した。次いで、ホットプレートを用いて、200℃で5分間加熱することで、着色組成物をパターニングしてシアン色画素を形成した。同様に赤色着色組成物、黄色着色組成物を同様のプロセスでパターニングして、赤色画素、黄色画素を順次形成して、シアン色画素、赤色画素および黄磯画素を有するカラーフィルタを形成した。赤色着色組成物、黄色着色組成物については後述する。このカラーフィルタにおいては、黄色画素がベイヤーパターンで形成されており、その隣接する領域に、赤色画素、シアン色画素がアイランドパターンで形成されている。得られたカラーフィルタを公知の方法に従い固体撮像素子に組み込んだ。この固体撮像素子は好適な画像認識能を有していた。
下記成分を混合し、撹拌した後、孔径0.45μmのナイロン製フィルタ(日本ポール(株)製)でろ過して、赤色着色組成物を調製した。
赤色顔料分散液 ・・51.7質量部
樹脂101 ・・・0.6質量部
重合性化合物(NKエステル A-DPH-12E、新中村化学工業(株)製) ・・・0.6質量部
光重合開始剤(Irgacure OXE01、BASF社製) ・・・0.4質量部
界面活性剤101 ・・・4.2質量部
紫外線吸収剤(UV-503、大東化学(株)製) ・・・0.3質量部
PGMEA ・・・42.6質量部
下記成分を混合し、撹拌した後、孔径0.45μmのナイロン製フィルタ(日本ポール(株)製)でろ過して、青色着色組成物を調製した。
黄色顔料分散液 44.9質量部
樹脂101 ・・・2.1質量部
重合性化合物(KAYARAD DPHA、日本化薬(株)製) ・・・1.5質量部
重合性化合物(NKエステル A-DPH-12E、新中村化学工業(株)製) ・・・0.7質量部
光重合開始剤(Irgacure OXE01、BASF社製) ・・・0.8質量部
界面活性剤101 ・・・4.2質量部
紫外線吸収剤(UV-503、大東化学(株)製) ・・・0.3質量部
PGMEA ・・・45.8質量部
C.I.ピグメントレッド254の9.6質量部、C.I.ピグメントイエロー139の4.3質量部、分散剤(Disperbyk-161、ビックケミー社製)の6.8質量部、PGMEAの79.3質量部とからなる混合液を、ビーズミル(ジルコニアビーズ0.3mm径)により3時間混合および分散して、顔料分散液を調製した。その後さらに、減圧機構付き高圧分散機NANO-3000-10(日本ビーイーイー(株)製)を用いて、2000kg/cm3の圧力下で流量500g/minとして分散処理を行なった。この分散処理を10回繰り返し、赤色顔料分散液を得た。
C.I.ピグメントイエロー150の12.1質量部、分散剤(Disperbyk-161、ビックケミー社製)の5.5質量部、PGMEAの82.4質量部とからなる混合液を、ビーズミル(ジルコニアビーズ0.3mm径)により3時間混合および分散して、顔料分散液を調製した。その後さらに、減圧機構付き高圧分散機NANO-3000-10(日本ビーイーイー(株)製)を用いて、2000kg/cm3の圧力下で流量500g/minとして分散処理を行なった。この分散処理を10回繰り返し、黄色顔料分散液を得た。
実施例1001の赤色着色組成物を下記マゼンタ色着色組成物に変更し、マゼンタ色画素を作成した以外は実施例1001と同様の方法によりカラーフィルタを形成した。得られたカラーフィルタを公知の方法に従い固体撮像素子に組み込んだ。この固体撮像素子は好適な画像認識能を有していた。
下記成分を混合し、撹拌した後、孔径0.45μmのナイロン製フィルタ(日本ポール(株)製)でろ過して、マゼンタ色着色組成物を調製した。
マゼンタ色顔料分散液 ・・・44.9質量部
樹脂101 ・・・2.1質量部
重合性化合物(KAYARAD DPHA、日本化薬(株)製) ・・・1.5質量部
重合性化合物(NKエステル A-DPH-12E、新中村化学工業(株)製) ・・・0.7質量部
光重合開始剤(Irgacure OXE01、BASF社製) ・・・0.8質量部
界面活性剤101 ・・・4.2質量部
紫外線吸収剤(UV-503、大東化学(株)製) ・・・0.3質量部
PGMEA ・・・45.8質量部
C.I.ピグメントレッド122の12.1質量部、分散剤(Disperbyk-161、ビックケミー社製)の5.5質量部、PGMEAの82.4質量部とからなる混合液を、ビーズミル(ジルコニアビーズ0.3mm径)により3時間混合および分散して、顔料分散液を調製した。その後さらに、減圧機構付き高圧分散機NANO-3000-10(日本ビーイーイー(株)製)を用いて、2000kg/cm3の圧力下で流量500g/minとして分散処理を行なった。この分散処理を10回繰り返し、マゼンタ色顔料分散液を得た。
Claims (14)
- 着色剤と、樹脂と、重合性化合物と、光重合開始剤と、紫外線吸収剤と、溶剤とを含む着色組成物であって、
前記着色剤は、無置換の銅フタロシアニン顔料と、ハロゲン化銅フタロシアニン顔料とを含み、
前記着色剤の全質量中における前記無置換の銅フタロシアニン顔料の含有量が10質量%以上であり、前記ハロゲン化銅フタロシアニン顔料の含有量が40質量%以上である、着色組成物。 - 前記無置換の銅フタロシアニン顔料は、カラーインデックスピグメントブルー15:4を含み、
前記ハロゲン化銅フタロシアニン顔料は、カラーインデックスピグメントグリーン7を含む、請求項1に記載の着色組成物。 - 前記着色剤の全質量中における前記無置換の銅フタロシアニン顔料と前記ハロゲン化銅フタロシアニン顔料との合計の含有量が70~100質量%である、請求項1または2に記載の着色組成物。
- 前記着色組成物を用いて膜厚が0.6μmの膜を形成した際に、前記膜の厚み方向における波長400~450nmの範囲の光の透過率の平均値が75%以上であり、前記膜の厚み方向における波長650~700nmの範囲の光の透過率の平均値が30%以下であり、透過率が50%を示す波長が波長560~590nmの範囲に存在する、請求項1~3のいずれか1項に記載の着色組成物。
- 着色剤と、樹脂と、重合性化合物と、光重合開始剤と、紫外線吸収剤と、溶剤とを含む着色組成物であって、
前記着色組成物を用いて膜厚が0.6μmの膜を形成した際に、前記膜の厚み方向における波長400~450nmの範囲の光の透過率の平均値が75%以上であり、前記膜の厚み方向における波長650~700nmの範囲の光の透過率の平均値が30%以下であり、透過率が50%を示す波長が波長560~590nmの範囲に存在する、着色組成物。 - 前記着色組成物の全固形分中における前記紫外線吸収剤の含有量が0.5質量%以上である、請求項1~5のいずれか1項に記載の着色組成物。
- 前記紫外線吸収剤は、波長365nmにおける吸光度A1に対する波長410nmにおける吸光度A2の比の値が0.06以下である、請求項1~6のいずれか1項に記載の着色組成物。
- 前記紫外線吸収剤は、共役ジエン化合物、ベンゾトリアゾール化合物、ジベンゾイル化合物およびトリアジン化合物から選ばれる少なくとも1種である、請求項1~7のいずれか1項に記載の着色組成物。
- 前記着色剤の100質量部に対して、前記樹脂を100~350質量部含む、請求項1~8のいずれか1項に記載の着色組成物。
- 前記着色剤の全質量中におけるカラーインデックスピグメントブルー15:4の含有量が10~50質量%であり、
前記着色組成物の全固形分中における前記光重合開始剤の含有量が3~10質量%であり、
前記着色組成物の全固形分中における前記紫外線吸収剤の含有量が1~10質量%である、請求項1~10のいずれか1項に記載の着色組成物。 - 請求項1~11のいずれか1項に記載の着色組成物から得られる膜。
- 請求項12に記載の膜を有するカラーフィルタ。
- 請求項12に記載の膜を有する固体撮像素子。
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JP2005049791A (ja) * | 2003-07-31 | 2005-02-24 | Fujifilm Arch Co Ltd | Lcd用カラーフィルタ |
JP2006098684A (ja) * | 2004-09-29 | 2006-04-13 | Fujifilm Electronic Materials Co Ltd | カラーフィルタ及び固体撮像素子 |
JP2008052239A (ja) * | 2006-01-13 | 2008-03-06 | Toyo Ink Mfg Co Ltd | カラーフィルタ用着色組成物、カラーフィルタおよび液晶表示装置 |
JP2013068814A (ja) * | 2011-09-22 | 2013-04-18 | Fujifilm Corp | 着色感放射線性組成物、カラーフィルタ及びそのカラーフィルタの製造方法、並びに、固体撮像素子 |
JP2018066992A (ja) * | 2016-10-21 | 2018-04-26 | 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. | 着色感光性樹脂組成物、これを利用して製造されたカラーフィルターおよび画像表示装置 |
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JP2005049791A (ja) * | 2003-07-31 | 2005-02-24 | Fujifilm Arch Co Ltd | Lcd用カラーフィルタ |
JP2006098684A (ja) * | 2004-09-29 | 2006-04-13 | Fujifilm Electronic Materials Co Ltd | カラーフィルタ及び固体撮像素子 |
JP2008052239A (ja) * | 2006-01-13 | 2008-03-06 | Toyo Ink Mfg Co Ltd | カラーフィルタ用着色組成物、カラーフィルタおよび液晶表示装置 |
JP2013068814A (ja) * | 2011-09-22 | 2013-04-18 | Fujifilm Corp | 着色感放射線性組成物、カラーフィルタ及びそのカラーフィルタの製造方法、並びに、固体撮像素子 |
JP2018066992A (ja) * | 2016-10-21 | 2018-04-26 | 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. | 着色感光性樹脂組成物、これを利用して製造されたカラーフィルターおよび画像表示装置 |
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