WO2022202204A1 - 着色組成物、膜、光学フィルタ、固体撮像素子および画像表示装置 - Google Patents
着色組成物、膜、光学フィルタ、固体撮像素子および画像表示装置 Download PDFInfo
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- WO2022202204A1 WO2022202204A1 PCT/JP2022/009249 JP2022009249W WO2022202204A1 WO 2022202204 A1 WO2022202204 A1 WO 2022202204A1 JP 2022009249 W JP2022009249 W JP 2022009249W WO 2022202204 A1 WO2022202204 A1 WO 2022202204A1
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Classifications
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- 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
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- 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
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- 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
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
- C08K5/23—Azo-compounds
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
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- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/22—Dyes with unsubstituted amino groups
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- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
- C09B11/20—Preparation from other triarylmethane derivatives, e.g. by substitution, by replacement of substituents
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- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/26—Triarylmethane dyes in which at least one of the aromatic nuclei is heterocyclic
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- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/28—Pyronines ; Xanthon, thioxanthon, selenoxanthan, telluroxanthon dyes
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- C09B19/02—Bisoxazines prepared from aminoquinones
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- C09B25/00—Quinophthalones
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- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
- C09B33/153—Disazo dyes in which the coupling component is a bis-(aceto-acetyl amide) or a bis-(benzoyl-acetylamide)
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- 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
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- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B55/00—Azomethine dyes
-
- 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
- C09B57/00—Other synthetic dyes of known constitution
-
- 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/04—Isoindoline dyes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/004—Mixtures of two or more reactive dyes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/006—Preparation of organic pigments
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- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
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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
- 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
Definitions
- the present invention relates to coloring compositions.
- the present invention also relates to a film, an optical filter, a solid-state imaging device, and an image display device using the colored composition.
- Optical filters such as color filters are manufactured using a coloring composition containing a coloring agent and a resin.
- Example 2 of Patent Document 1 and Example 6 of Patent Document 2 a coloring composition containing Color Index Pigment Green 36 and Color Index Pigment Yellow 155 is used to form a green pixel of a color filter. Have been described.
- the colorant concentration in the total solid content of the coloring composition increases, the ratio of components other than the colorant relatively decreases. Therefore, as the colorant concentration in the total solid content of the coloring composition increases, the moisture resistance of the obtained film tends to decrease, and when the film is exposed to a high humidity environment, There was a tendency for the colorant to agglomerate, etc., to easily generate foreign matter.
- an object of the present invention is to provide a coloring composition capable of forming a film with excellent moisture resistance.
- Another object of the present invention is to provide a film, an optical filter, a solid-state imaging device, and an image display device which are excellent in moisture resistance.
- the present invention provides the following.
- a coloring composition containing a coloring agent and a resin, the colorant comprises Color Index Pigment Yellow 155; A coloring composition, wherein the content of Color Index Pigment Yellow 155 in the total solid content of the coloring composition is 16% by mass or more.
- the coloring agent includes a yellow coloring agent other than Color Index Pigment Yellow 155.
- the yellow colorant other than Color Index Pigment Yellow 155 is at least one selected from Color Index Pigment Yellow 129 and Color Index Pigment Yellow 150.
- ⁇ 4> The coloring composition according to any one of ⁇ 1> to ⁇ 3>, wherein the content of Color Index Pigment Yellow 155 in the coloring agent is 40% by mass or more.
- R 1 to R 6 each independently represent a substituent
- R 11 to R 22 each independently represent a hydrogen atom or a substituent.
- ⁇ 6> The coloring composition according to any one of ⁇ 1> to ⁇ 5>, wherein the coloring agent contains at least one selected from a green coloring agent and a red coloring agent.
- ⁇ 11> The colored composition according to any one of ⁇ 1> to ⁇ 10>, wherein the resin includes a resin having a cyclic ether group.
- ⁇ 12> The colored composition according to any one of ⁇ 1> to ⁇ 11>, further comprising a polymerizable compound and a photopolymerization initiator.
- ⁇ 13> The colored composition according to any one of ⁇ 1> to ⁇ 12>, which is used for color filters.
- ⁇ 14> A film obtained from the colored composition according to any one of ⁇ 1> to ⁇ 13>.
- An optical filter comprising the film according to ⁇ 14>.
- ⁇ 16> A solid-state imaging device having the film according to ⁇ 14>.
- ⁇ 17> An image display device comprising the film according to ⁇ 14>.
- the present invention it is possible to provide a coloring composition capable of forming a film with excellent moisture resistance.
- the present invention can provide films, optical filters, solid-state imaging devices, and image display devices that are excellent in moisture resistance.
- ⁇ 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 and a resin, the colorant comprises Color Index Pigment Yellow 155; The content of Color Index Pigment Yellow 155 in the total solid content of the coloring composition is 16% by mass or more.
- the second aspect of the coloring composition of the present invention is A coloring composition containing a coloring agent and a resin,
- the coloring agent contains a compound represented by formula (1),
- the content of the compound represented by formula (1) in the total solid content of the coloring composition is 16% by mass or more.
- R 1 to R 6 each independently represent a substituent
- R 11 to R 22 each independently represent a hydrogen atom or a substituent.
- the coloring composition of the present invention a film with excellent moisture resistance can be formed.
- the content of Color Index Pigment Yellow 155 in the total solid content of the coloring composition or the compound represented by the above formula (1) is 16% by mass. It is presumed that due to this, it was possible to form a strong film that is difficult for moisture to penetrate into the film and movement of materials in the film, and as a result, a film with excellent moisture resistance was formed. presumed to have been able to
- the coloring composition of the present invention Even if the content of the colorant in the total solid content of the product is high (for example, 16% by mass or more), a film with excellent moisture resistance can be formed. Therefore, when the content of the coloring agent in the total solid content of the coloring composition is high (preferably, when the content of the coloring agent in the total solid content of the coloring composition is 45% by mass or more), the present The effects of the invention are remarkably exhibited.
- the coloring composition of the present invention contains Color Index Pigment Yellow 155 or a coloring agent containing the compound represented by the above formula (1), it has excellent storage stability. Although the detailed reason why such an effect is obtained is unknown, it is presumed that Color Index Pigment Yellow 155 or the compound represented by the above formula (1) is excellent in dispersion stability. .
- the coloring composition of the present invention is preferably used as a coloring composition for optical filters.
- optical filters include color filters and infrared transmission filters, and color filters are preferred. That is, the coloring composition of the present invention is preferably used as a coloring composition for color filters. More specifically, it can be preferably used as a coloring composition for forming pixels of a color filter. Pixel types include red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, and yellow pixels. Red pixels, green pixels, and yellow pixels are preferred. More preferably, it is a green pixel.
- the maximum transmittance in the wavelength range of 400 to 640 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum transmittance in the wavelength range of 1100 to 1300 nm.
- Filters satisfying spectral characteristics with a value of 70% or more are preferred.
- the infrared transmission filter is preferably a filter that satisfies any one of the following spectral characteristics (1) to (5).
- the maximum transmittance in the wavelength range of 400 to 640 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum transmittance in the wavelength range of 800 to 1500 nm is A filter that is 70% or more (preferably 75% or more, more preferably 80% or more).
- the maximum transmittance in the wavelength range of 400 to 750 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum transmittance in the wavelength range of 900 to 1500 nm is A filter that is 70% or more (preferably 75% or more, more preferably 80% or more).
- the maximum transmittance in the wavelength range of 400 to 830 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum transmittance in the wavelength range of 1000 to 1500 nm is A filter that is 70% or more (preferably 75% or more, more preferably 80% or more).
- the maximum transmittance in the wavelength range of 400 to 950 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum transmittance in the wavelength range of 1100 to 1500 nm is A filter that is 70% or more (preferably 75% or more, more preferably 80% or more).
- the maximum transmittance in the wavelength range of 400 to 1050 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum transmittance in the wavelength range of 1200 to 1500 nm is A filter that is 70% or more (preferably 75% or more, more preferably 80% or more).
- the colored composition of the present invention is preferably used for solid-state imaging devices. More specifically, it is preferably used as a coloring composition for optical filters used for solid-state imaging devices, and more preferably used as a coloring composition for color filters used for solid-state imaging devices.
- the solid content concentration of the coloring composition of the present invention is preferably 5 to 30% by mass.
- the lower limit is more preferably 7.5% by mass or more, and even more preferably 10% by mass or more.
- the upper limit is more preferably 25% by mass or less, and even more preferably 20% by mass or less.
- the coloring composition of the present invention contains a coloring agent.
- C.I. I. Color Index
- Pigment Yellow 155 or one containing the compound represented by formula (1) is used.
- C.I. I. Pigment Yellow 155 and the compound represented by formula (1) are collectively referred to as a specific colorant.
- R 1 to R 6 each independently represent a substituent
- R 11 to R 22 each independently represent a hydrogen atom or a substituent.
- substituents represented by R 1 to R 6 in formula (1) include alkyl groups, alkenyl groups, alkynyl groups, and aryl groups, with alkyl groups being preferred.
- the number of carbon atoms in the alkyl group is preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 10, even more preferably 1 to 5, and particularly preferably 1 to 3.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear.
- the alkenyl group preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, still more preferably 2 to 10 carbon atoms, even more preferably 2 to 5 carbon atoms, and particularly preferably 2 or 3 carbon atoms.
- the alkenyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear.
- the alkynyl group preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, still more preferably 2 to 10 carbon atoms, even more preferably 2 to 5 carbon atoms, and particularly preferably 2 or 3 carbon atoms.
- the alkynyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear.
- the number of carbon atoms in the aryl group is preferably 6-30, more preferably 6-20, even more preferably 6-12.
- Alkyl groups, alkenyl groups, alkynyl groups and aryl groups may have substituents.
- a halogen atom etc. are mentioned as a substituent.
- R 1 to R 6 in formula (1) are particularly preferably methyl groups.
- R 11 to R 22 in formula (1) each independently represent a hydrogen atom or a substituent.
- substituents include halogen atoms, alkyl groups, alkenyl groups, alkynyl groups, and aryl groups.
- R 11 to R 22 in formula (1) are preferably hydrogen atoms.
- the compound represented by Formula (1) is preferably a compound represented by Formula (1-1) below.
- the compound represented by formula (1-1) is C.I. I. Pigment Yellow 155.
- the specific coloring agent is preferably a yellow coloring agent.
- the coloring agent contained in the coloring composition of the present invention can further contain a coloring agent (another coloring agent) other than the specific coloring agent.
- a coloring agent another coloring agent
- Other colorants used in combination include green colorants, red colorants, yellow colorants, purple colorants, blue colorants, cyan colorants, orange colorants, and the like.
- the other coloring agent is preferably at least one selected from a yellow coloring agent, a green coloring agent and a red coloring agent, more preferably at least one selected from a green coloring agent and a red coloring agent. Colorants are more preferred.
- Other coloring agents may be pigments or dyes, but are preferably pigments.
- green colorants examples include phthalocyanine compounds and squarylium compounds, and phthalocyanine compounds are preferred.
- the green colorant is preferably a pigment, more preferably a phthalocyanine pigment.
- the phthalocyanine pigment is preferably a phthalocyanine pigment having a central metal (also referred to as a metal phthalocyanine pigment).
- Metal phthalocyanine pigments include copper phthalocyanine pigments, zinc phthalocyanine pigments, aluminum phthalocyanine pigments, and the like. Copper phthalocyanine pigments and zinc phthalocyanine pigments are preferred because they can form films with more excellent moisture resistance. Zinc phthalocyanine pigments are more preferred.
- the metal phthalocyanine pigment is preferably a halogenated phthalocyanine pigment, more preferably a halogenated copper phthalocyanine pigment or a halogenated zinc phthalocyanine pigment, and even more preferably a halogenated zinc phthalocyanine pigment.
- the halogenated phthalocyanine pigment is a phthalocyanine pigment having a halogen atom as a substituent.
- a copper phthalocyanine pigment is a phthalocyanine pigment having a copper atom as a central metal.
- a zinc phthalocyanine pigment is a phthalocyanine pigment having a zinc atom as a central metal.
- An aluminum phthalocyanine pigment is a phthalocyanine pigment having an aluminum atom as a central metal.
- green colorants include C.I. I. Green pigments such as Pigment Green 7, 10, 36, 37, 58, 59, 62, 63, 64, 65 and 66 are included. Further, as a green colorant, a halogenated zinc phthalocyanine having an average number of halogen atoms of 10 to 14, an average number of bromine atoms of 8 to 12, and an average number of chlorine atoms of 2 to 5 per molecule. Pigments can also be used. Specific examples include compounds described in International Publication No. 2015/118720. In addition, as a green colorant, the compound described in Chinese Patent Application No.
- 106909027 the phthalocyanine compound having a phosphoric acid ester as a ligand described in WO 2012/102395, described in JP 2019-008014.
- the phthalocyanine compound, the phthalocyanine compound described in JP-A-2018-180023, the compound described in JP-A-2019-038958, the aluminum phthalocyanine compound described in JP-A-2020-070426, JP-A-2020-076995 Core-shell type dyes described in, diarylmethane compounds described in JP-A-2020-504758, and the like can also be used.
- the green coloring agent is C.I. I. Pigment Green 7, 36, 58, 59, 62 and 63 are preferred, C.I. I. Pigment Green 7, 58, and 59 are more preferred, and C.I. I. Pigment Greens 58 and 59 are more preferred, and C.I. I. Pigment Green 58 is particularly preferred.
- red colorants examples include diketopyrrolopyrrole compounds, anthraquinone compounds, azo compounds, naphthol compounds, azomethine compounds, xanthene compounds, quinacridone compounds, perylene compounds, and thioindigo compounds.
- the red colorant is preferably a pigment, more preferably a diketopyrrolopyrrole pigment, anthraquinone pigment, azo pigment, naphthol pigment, azomethine pigment, xanthene pigment, quinacridone pigment, perylene pigment or thioindigo pigment.
- Ketopyrrolopyrrole pigments are more preferred.
- red colorants include C.I. I. (Color Index) Pigment Red 1, 2, 3, 4, 5, 6, 7, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48: 1, 48: 2, 48: 3, 48:4, 49, 49:1, 49:2, 52:1, 52:2, 53:1, 57:1, 60:1, 63:1, 66, 67, 81:1, 81:2, 81: 3, 83, 88, 90, 105, 112, 119, 122, 123, 144, 146, 149, 150, 155, 166, 168, 169, 170, 171, 172, 175, 176, 177, 178, 179, 184, 185, 187, 188, 190, 200, 202, 206, 207, 208, 209, 210, 216, 220, 224, 226, 242, 246, 254, 255, 264, 269, 270, 272, 279, 291, 294, 295, 296, 297 and other red pigments.
- a red colorant a diketopyrrolopyrrole compound in which at least one bromine atom is substituted in the structure described in JP-A-2017-201384, a diketopyrrolopyrrole described in paragraphs 0016 to 0022 of Japanese Patent No.
- 10-2019-0140741 anthraquinone compounds described in Korean Patent Publication No. 10-2019-0140744, JP 2020 -Perylene compounds described in JP-A-079396, perylene compounds described in JP-A-2020-083982, xanthene compounds described in JP-A-2018-035345, paragraph numbers 0025 to 0041 of JP-A-2020-066702
- the described diketopyrrolopyrrole compounds and the like can also be used.
- red colorant a compound having a structure in which an aromatic ring group in which a group having an oxygen atom, a sulfur atom or a nitrogen atom is bonded to an aromatic ring is bonded to a diketopyrrolopyrrole skeleton is used.
- Lumogen F Orange 240 manufactured by BASF, red pigment, perylene pigment
- red colorant can also be used as a red colorant.
- C.I. I. Pigment Red 122, 177, 179, 254, 255, 264, 269, 272 and 291 are preferred, and C.I. I. Pigment Red 254, 264, 272 are more preferred.
- yellow colorants examples include azo compounds, azomethine compounds, isoindoline compounds, pteridine compounds, quinophthalone compounds and perylene compounds.
- the yellow colorant is preferably a pigment, more preferably an azo pigment, an azomethine pigment, an isoindoline pigment, a pteridine pigment, a quinophthalone pigment or a perylene pigment, because the storage stability of the colored composition can be further improved. Therefore, it is more preferably an azo pigment or an azomethine pigment.
- Specific examples of yellow colorants include C.I. I.
- an azobarbiturate nickel complex having the following structure can also be used.
- X 1 to X 16 each independently represent a hydrogen atom or a halogen atom, and Z 1 represents an alkylene group having 1 to 3 carbon atoms.
- Specific examples of the compound represented by formula (QP1) include compounds described in paragraph number 0016 of Japanese Patent No. 6443711 .
- Y 1 to Y 3 each independently represent a halogen atom.
- n and m are integers of 0 to 6; p is an integer of 0 to 5; (n+m) is 1 or more.
- Specific examples of the compound represented by formula (QP2) include compounds described in paragraphs 0047 to 0048 of Japanese Patent No. 6432077.
- C.I. I. Pigment Yellow 129, 138, 139, 150 and 185 are preferred, and C.I. I. Pigment Yellow 129,150 is more preferred.
- C.I. I. Pigment Orange 2 5, 13, 16, 17: 1, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 71, 73, etc. of orange pigments.
- C.I. I. Purple pigments such as Pigment Violet 1, 19, 23, 27, 32, 37, 42, 60, 61 are included.
- C.I. I. pigment blue 1, 2, 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 22, 29, 60, 64, 66, 79, 80, 87, 88, etc. be done.
- An aluminum phthalocyanine compound having a phosphorus atom can also be used as a blue colorant. Specific examples include compounds described in paragraph numbers 0022 to 0030 of JP-A-2012-247591 and paragraph number 0047 of JP-A-2011-157478.
- the diketopyrrolopyrrole pigment has a crystallite size of 140 ⁇ or less in the plane direction corresponding to the maximum peak in the X-ray diffraction pattern among the eight planes ( ⁇ 1 ⁇ 1 ⁇ 1) of the crystal lattice planes. It is also preferred to use one.
- the physical properties of the diketopyrrolopyrrole pigment are preferably set as described in paragraphs 0028 to 0073 of JP-A-2020-097744.
- the pigment it is also preferable to use a halogenated zinc phthalocyanine pigment having a Raman spectrum described in Japanese Patent No. 6744002 from the viewpoint of enhancing spectral characteristics.
- the organic pigment it is also preferable to use a dioxazine pigment with a controlled contact angle described in WO 2019/107166 from the viewpoint of viscosity adjustment.
- Dyes can also be used as other coloring agents.
- the dye is not particularly limited, and known dyes can be used.
- Pigment multimers can also be used for other coloring agents.
- the dye multimer is preferably a dye dissolved in a solvent and used. Further, the dye multimer may form particles. When the dye multimer is particles, it is usually used in a state of being dispersed in a solvent.
- the particulate dye multimer can be obtained, for example, by emulsion polymerization, and specific examples include the compounds and production methods described in JP-A-2015-214682.
- a dye multimer has two or more dye structures in one molecule, and preferably has three or more dye structures. The upper limit is not particularly limited, but may be 100 or less.
- a plurality of dye structures in one molecule may be the same dye structure or different dye structures.
- the weight average molecular weight (Mw) of the dye multimer is preferably 2,000 to 50,000.
- the lower limit is more preferably 3000 or more, and even more preferably 6000 or more.
- the upper limit is more preferably 30,000 or less, and even more preferably 20,000 or less.
- Dye multimers, JP-A-2011-213925, JP-A-2013-041097, JP-A-2015-028144, JP-A-2015-030742, JP-A-2016-102191, International Publication No. 2016/ Compounds described in No. 031442, etc., triarylmethane dye polymers described in Korean Patent Publication No. 10-2020-0028160, triarylmethane dye polymers described in JP-A-2019-139240, etc. can also be used.
- colorants include thiazole compounds described in JP-A-2012-158649, azo compounds described in JP-A-2011-184493, azo compounds described in JP-A-2011-145540, JP-A-2020- 117638, the xanthene compound described in JP-A-2020-079397, the perylene dye described in JP-A-2020-084169, the xanthene dye described in JP-A-2019-053303, the JP-A Tetraazaporphyrin dyes described in JP-A-2019-116544, triarylmethane compounds described in JP-A-2019-152852, squarylium dyes described in JP-A-2020-021063, JP-A-2020-128494 squarylium dye, the squarylium dye described in JP-A-2020-183509, the phthalocyanine compound described in WO2020/174991, the isoindoline compound described in JP-A-2020-160279, or
- the coloring composition of the present invention further contains a green coloring agent in addition to the specific coloring agent described above, it is preferably used as a coloring composition for forming green pixels of color filters.
- the coloring composition of the present invention further contains a red coloring agent in addition to the specific coloring agent described above, it is preferably used as a coloring composition for forming red pixels of a color filter.
- the coloring agent contained in the coloring composition may include two or more chromatic coloring agents, and a combination of the two or more chromatic coloring agents may form a black color.
- a colored composition is preferably used as a colored composition for forming an infrared transmission filter.
- the combination of chromatic colorants includes the following.
- the yellow colorant may be only the specific colorant described above, or may further contain a colorant other than the specific colorant.
- An embodiment containing a yellow colorant, a green colorant, a purple colorant and a red colorant (2) An embodiment containing a yellow colorant, a green colorant, a purple colorant and a red colorant. (3) An embodiment containing a yellow colorant, a cyan colorant, a purple colorant and a red colorant. (4) An embodiment containing a yellow colorant, a blue colorant and a red colorant. (5) An embodiment containing a yellow colorant, a green colorant and a red colorant. (6) An embodiment containing a yellow colorant, a cyan colorant and a red colorant. (7) An embodiment containing a yellow colorant, a purple colorant and a red colorant.
- the content of the coloring agent in the total solid content of the coloring composition is preferably 45% by mass or more, more preferably 50% by mass or more, and even more preferably 55% by mass or more.
- the upper limit is preferably 65% by mass or less, more preferably 60% by mass or less.
- the content of the specific coloring agent in the total solid content of the coloring composition is 16% by mass or more, preferably 20% by mass or more, and more preferably 25% by mass or more.
- the upper limit is preferably 65% by mass or less, more preferably 60% by mass or less.
- the content of the specific coloring agent in the coloring agent is preferably 25% by mass or more, more preferably 28% by mass or more, further preferably 35% by mass or more, and 40% by mass. It is particularly preferable that it is above.
- the content of Pigment Yellow 155 is 16% by mass or more, preferably 20% by mass or more, and more preferably 25% by mass or more.
- the upper limit is preferably 65% by mass or less, more preferably 60% by mass or less.
- the content of Pigment Yellow 155 is preferably 25% by mass or more, more preferably 28% by mass or more, still more preferably 35% by mass or more, and particularly preferably 40% by mass or more.
- the content of the yellow colorant other than the specific colorant in the colorant is preferably 1 to 50% by mass.
- the upper limit is more preferably 40% by mass or less, and even more preferably 30% by mass or less.
- the lower limit is more preferably 5% by mass or more, and even more preferably 10% by mass or more.
- the content of the yellow colorant other than the specific colorant is preferably 1 to 100 parts by mass with respect to 100 parts by mass of the specific colorant.
- the upper limit is more preferably 90 parts by mass or less, and even more preferably 80 parts by mass or less.
- the lower limit is more preferably 10 parts by mass or more, and even more preferably 50 parts by mass or more.
- the yellow colorant other than the specific colorant is C.I. I. Pigment Yellow 129 and C.I. I. Pigment Yellow 150, when it contains at least one selected from C.I. I. Pigment Yellow 129 and C.I. I.
- the content of Pigment Yellow 150 is preferably 1 to 100 parts by mass with respect to 100 parts by mass of the specific colorant.
- the upper limit is more preferably 90 parts by mass or less, and even more preferably 80 parts by mass or less.
- the lower limit is more preferably 10 parts by mass or more, and even more preferably 50 parts by mass or more.
- the coloring composition of the present invention is used as a coloring composition for forming green pixels of a color filter, it is preferable to use a coloring agent containing a yellow coloring agent and a green coloring agent.
- the yellow colorant preferably contains a specific colorant.
- the content of the specific coloring agent in the yellow coloring agent is preferably 30% by mass or more, more preferably 50% by mass or more.
- the content of the specific colorant is preferably 30 to 100 parts by mass with respect to 100 parts by mass of the green colorant.
- the lower limit is more preferably 40 parts by mass or more, and even more preferably 50 parts by mass or more.
- the upper limit is more preferably 90 parts by mass or less, and even more preferably 80 parts by mass or less.
- the coloring composition of the present invention is used as a coloring composition for forming red pixels of a color filter, it is preferable to use a coloring agent containing a yellow coloring agent and a red coloring agent.
- the yellow colorant preferably contains a specific colorant.
- the content of the specific coloring agent in the yellow coloring agent is preferably 50% by mass or more, more preferably 60% by mass or more.
- the content of the specific coloring agent is preferably 20 to 90 parts by weight with respect to 100 parts by weight of the red coloring agent.
- the lower limit is more preferably 30 parts by mass or more, and even more preferably 40 parts by mass or more.
- the upper limit is more preferably 80 parts by mass or less, and even more preferably 70 parts by mass or less.
- the content of the yellow coloring agent in the coloring agent is preferably 80% by mass or more, and is 90% by mass or more. is more preferable, and 95% by mass or more is even more preferable.
- the specific coloring agent is preferably a yellow coloring agent.
- the content of the specific coloring agent in the yellow coloring agent is preferably 30% by mass or more, more preferably 40% by mass or more, and even more preferably 50% by mass or more.
- the upper limit can be 100% by mass, 95% by mass or less, or 90% by mass or less.
- 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 more preferably 1,000,000 or less, and even more preferably 500,000 or less.
- the lower limit is more preferably 4000 or more, and even 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 resin having an acid group preferably contains a repeating unit having an acid group on its side chain, and more preferably contains 5 to 70 mol % of repeating units having an acid group on its side chain in all repeating units of the resin.
- the upper limit of the content of repeating units having an acid group in a side chain is more preferably 50 mol % or less, and even more preferably 30 mol % or less.
- the lower limit of the content of repeating units having an acid group in a side chain is more preferably 10 mol % or more, and even 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 more preferably 10 mgKOH/g or more, still more preferably 20 mgKOH/g or more.
- the upper limit is more preferably 200 mgKOH/g or less, still 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.).
- a resin having an ethylenically unsaturated bond-containing group As the resin, it is also preferable to use a resin having an ethylenically unsaturated bond-containing group.
- ethylenically unsaturated bond-containing groups include vinyl groups, styrene groups, (meth)allyl groups, and (meth)acryloyl groups.
- the resin it is also preferable to use a resin having a cyclic ether group.
- a film having better moisture resistance can be formed.
- the cyclic ether group include an epoxy group and an oxetanyl group, with the epoxy group being preferred.
- the epoxy group is preferably an alicyclic epoxy group because it facilitates the formation of a film having excellent moisture resistance.
- 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 a group 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 moisture 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 (A1-1) and repeating units represented by formula (A1-2). .
- the resin may contain only one of the repeating units represented by the formula (A1-1) and the repeating unit represented by the formula (A1-2).
- a repeating unit represented by 1) and a repeating unit represented by formula (A1-2) may be included.
- the ratio of the repeating unit represented by the formula (A1-1) to the repeating unit represented by the formula (A1-2) is the molar ratio represented by the formula (A1-1)
- Repeating unit: repeating unit represented by formula (A1-2) preferably 5:95 to 95:5, more preferably 10:90 to 90:10, 20:80 to 80 :20 is more preferred.
- L A1 represents a single bond or a divalent linking group
- R A1 represents a hydrogen atom or a substituent.
- the substituent represented by R A1 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, and even more preferably 1-3.
- R A1 is preferably a hydrogen atom or a methyl group.
- the divalent linking group represented by L 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.
- 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 more preferably 90 mol % or less, and even more preferably 80 mol % or less.
- the lower limit is more preferably 2 mol % or more, still 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. In formula (Y1), 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 a monocyclic cycloalkyl group such as a cyclopentyl group and a cyclohexyl group, a norbornyl group, a tetracyclodecanyl group, a 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 for 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). In addition, repeating units B-3 include repeating units 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.
- Formula (B3) In, X b3 represents a trivalent linking group, L b3 represents a single bond or a divalent linking group, and 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 A system linking group is 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 carboxy group, a sulfo group, and a phosphoric acid group, preferably a phenolic hydroxy group or a carboxy group, more preferably a carboxy 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 more preferably 60 mol % or less, even more preferably 40 mol % or less.
- the lower limit is more preferably 8 mol % or more, still 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 more preferably 45 mol % or less, even more preferably 30 mol % or less.
- the lower limit is more preferably 2 mol % or more, still 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 more preferably 45 mol % or less, even more preferably 30 mol % or less.
- the lower limit is more preferably 2 mol % or more, still 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 more preferably 45 mol % or less, even more preferably 30 mol % or less.
- the lower limit is more preferably 2 mol % or more, still 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 having a cyclic ether group As the resin having a cyclic ether group, jER1031S (manufactured by Mitsubishi Chemical Corporation), BATG (manufactured by Showa Denko K.K.) and the like can also be used. Further, as the resin having a cyclic ether group, resins described in paragraphs 0034 to 0036 of JP-A-2013-011869, resins described in paragraphs 0147-0156 of JP-A-2014-043556, in particular Resins described in paragraph numbers 0085 to 0092 of JP-A-2014-089408, resins described in JP-A-2017-179172, paragraph numbers 0027-0055 and 0096 of JP-A-2018-180081 Resins, resins described in Paragraph Nos. 0117 to 0120 of JP-T-2020-515680, and resins described in Paragraph No. 0084 of International Publication No. 2020/175011 can also be used.
- 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- is preferably a hydrocarbon group or a group of a combination of a hydrocarbon group and —O—.
- 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 more preferably 1000 or more.
- the upper limit is more preferably 10,000 or less, even 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 content of the resin in the total solid content of the coloring composition is preferably 5-40% by mass.
- the upper limit is more preferably 35% by mass or less, and even more preferably 30% by mass or less.
- the lower limit is more preferably 8% by mass or more, and even more preferably 10% by mass or more.
- the content of the resin having a cyclic ether group in the total solid content of the coloring composition is preferably 1 to 30% by mass.
- the upper limit is more preferably 20% by mass or less, and even more preferably 10% by mass or less.
- the lower limit is more preferably 2% by mass or more, and even more preferably 3% by mass or more.
- the content of the resin having a cyclic ether group in the resin is preferably 5 to 100% by mass, more preferably 10 to 100% by mass, and even more preferably 20 to 100% by mass.
- the coloring composition of the present invention may contain only one type of resin, or may contain two or more types. When two or more resins are included, the total amount thereof is preferably within the above range.
- the coloring composition of the present invention preferably contains a polymerizable compound.
- the polymerizable compound include compounds having an ethylenically unsaturated bond-containing group.
- 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 more preferably 2000 or less, and even more preferably 1500 or less.
- the lower limit is more preferably 150 or more, even more preferably 250 or more.
- the lower limit is more preferably 3 mmol/g or more, still more preferably 4 mmol/g or more, and even more preferably 5 mmol/g or more.
- the upper limit is more preferably 12 mmol/g or less, even 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
- M-460 manufactured by Toagosei Co., Ltd.
- pentaerythritol tetra (meth) acrylate Shin-Nakamura Chemical Co., Ltd.
- NK Ester A-TMMT 1,6-hexanediol diacrylate
- KAYARAD HDDA 1,6-hexanediol diacrylate
- RP-1040 manufactured by Nippon Kayaku Co., Ltd.
- Aronix TO-2349 Toa Synthetic Co., Ltd.
- NK Oligo UA-7200 Shin-Nakamura Chemical Co., Ltd.
- 8UH-1006 8UH-1012 (Taisei Fine Chemical Co., Ltd.)
- Light acrylate POB-A0 Koreanoeisha Chemical Co., Ltd.
- EBECRYL80 manufactured by Daicel Allnex, tetrafunctional acrylate containing amine
- 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 as the polymerizable compound.
- the polymerizable compound having a fluorene skeleton is preferably a bifunctional polymerizable compound.
- Polymerizable compounds having a fluorene skeleton include compounds having a partial structure represented by the following formula (Fr).
- a wavy line represents a bond
- R f1 and R f2 each independently represent a substituent
- m and n each independently represent an integer of 0 to 5.
- m R f1 may be the same or different, and two R f1 out of m R f1 are bonded to form a ring; good too.
- n R f2 may be the same or different, and two R f2 out of n R f2 are bonded to form a ring; good too.
- Substituents represented by R f1 and R f2 include a halogen atom, a cyano group, a nitro group, an alkyl group, an aryl group, a heteroaryl group, —OR f11 , —COR f12 , —COOR f13 , —OCOR f14 and —NR f15 .
- R f16 —NHCOR f17 , —CONR f18 R f19 , —NHCONR f20 R f21 , —NHCOOR f22 , —SR f23 , —SO 2 R f24 , —SO 2 OR f25 , —NHSO 2 R f26 or —SO 2 NR f27 and R f28 .
- R f11 to R f28 each independently represent a hydrogen atom, an alkyl group, an aryl group or a heteroaryl group.
- polymerizable compounds having a fluorene skeleton include compounds having the following structures.
- Commercially available polymerizable compounds having a fluorene skeleton include Ogsol EA-0200 and EA-0300 (manufactured by Osaka Gas Chemicals Co., Ltd., (meth)acrylate monomers 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 1 to 35% by mass.
- the upper limit is more preferably 30% by mass or less, and even more preferably 25% by mass or less.
- the lower limit is more preferably 2% by mass or more, and even more preferably 5% 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 preferably 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-phenylpropan-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 of the aromatic ring group Ar OX1 include an acyl group, a nitro group, a trifluoromethyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, and a cyano group.
- 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 a group, an arylsulfonyl group, an acyl group, an acyloxy group, an amino group, a phosphinoyl group, a carbamoyl group or a sulfamoyl group
- R X2 is an alkyl group, alkenyl group, alkoxy group, aryl group, aryloxy group, heterocyclic 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.
- the lower limit is more preferably 0.5% by mass or more, and even more preferably 1% by mass or more.
- the upper limit is more preferably 15% by mass or less, and even more preferably 10% by mass or less.
- only one type of photopolymerization initiator may be used, or two or more types may be used. When two or more kinds are used, it is preferable that the total amount thereof is within the above range.
- the coloring composition of the present invention preferably 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 off a small amount of environmentally regulated substances it is also useful to azeotrope with a solvent having a boiling point equivalent to that of the solvent in order to increase the efficiency.
- a polymerization inhibitor or the like is added and distilled off under reduced pressure in order to suppress the radical polymerization reaction from progressing during the vacuum distillation and the intermolecular cross-linking.
- These distillation methods are the raw material stage, the reaction product of the raw materials (for example, the resin solution or polyfunctional monomer solution after polymerization), or the colored composition stage produced by mixing these compounds. It is possible at any stage such as
- the coloring composition of the present invention contains a compound (hereinafter also referred to as a specific amine compound) having 3 or more basic groups in one molecule, an amine value of 2.7 mmol/g or more, and a molecular weight of 100 or more.
- a compound hereinafter also referred to as a specific amine compound having 3 or more basic groups in one molecule, an amine value of 2.7 mmol/g or more, and a molecular weight of 100 or more.
- the molecular weight of the specific amine compound 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 value of the molecular weight of the specific amine compound when the molecular weight can be calculated from the structural formula, the molecular weight of the specific amine compound is the value calculated from the structural formula.
- 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 specific amine compound is preferably 5 mmol/g or more, more preferably 10 mmol/g or more, and even more preferably 15 mmol/g or more.
- the number of basic groups contained in the specific amine compound is preferably 4 or more, more preferably 6 or more, and even more preferably 10 or more.
- the basic group possessed by the specific amine compound is preferably an amino group.
- the specific amine compound is preferably a compound having a primary amino group, more preferably a compound containing a primary amino group and a tertiary amino group, respectively. Further preferred are compounds each containing a group and a tertiary amino group.
- the amino group possessed by the specific amine compound may be a cyclic amino group.
- the cyclic amino group may be an aliphatic cyclic amino group such as a piperidino group or an aromatic cyclic amino group such as a pyridyl group.
- the cyclic amino group is preferably a cyclic amino group having a 5- or 6-membered ring structure, more preferably a cyclic amino group having a 6-membered ring structure, and an aliphatic cyclic amino group having a 6-membered ring structure. more preferably a group.
- the cyclic amino group preferably has a hindered amine structure, particularly preferably a 6-membered ring hindered amine structure.
- the hindered amine structure preferably has a substituent such as an alkyl group on two carbon atoms in the ring structure adjacent to the nitrogen atom of the cyclic amino group.
- Cyclic amino groups having a hindered amine structure include, for example, 1,2,2,6,6-pentamethylpiperidyl group, 2,2,6,6-tetramethylpiperidyl group and 1,2,6,6-trimethylpiperidyl group, 2,6-dimethylpiperidyl group, 1-methyl-2,6-di(t-butyl)piperidyl group, 2,6-di(t-butyl)piperidyl group, 1,2,2,5,5- Pentamethylpyrrolidyl group, 2,2,5,5-tetramethylpyrrolidyl group, and the like.
- a 1,2,2,6,6-pentamethylpiperidyl group or a 2,2,6,6-tetramethylpiperidyl group is preferable, and a 1,2,2,6,6-pentamethylpiperidyl group is more preferred.
- the specific amine compound is preferably a polyalkyleneimine because it can further improve the storage stability of the colored composition.
- a polyalkyleneimine is a polymer obtained by ring-opening polymerization of an alkyleneimine and has at least a secondary amino group.
- the polyalkyleneimine may contain a primary amino group or a tertiary amino group in addition to the secondary amino group.
- the polyalkyleneimine is preferably 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.
- 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.).
- a compound having a cyclic amino group can also be used as the specific amine compound.
- examples of such compounds include compounds having the structures shown below.
- Commercially available products include ADEKA STAB LA-52, LA-57, LA-63P, and LA-68 (manufactured by ADEKA Corporation).
- the content of the specific amine compound in the total solid content of the coloring composition is preferably 0.1 to 5% by mass.
- the lower limit is more preferably 0.2% by mass or more, still more preferably 0.5% by mass or more, and even more preferably 1% by mass or more.
- the upper limit is more preferably 4.5% by mass or less, even more preferably 4% by mass or less, and even more preferably 3% by mass or less.
- the content of the specific amine compound is preferably 0.5 to 20 parts by mass with respect to 100 parts by mass of the pigment.
- the lower limit is more preferably 0.6 parts by mass or more, still more preferably 1 part by mass or more, and even more preferably 2 parts by mass or more.
- the upper limit is more preferably 10 parts by mass or less, and even more preferably 8 parts by mass or less. Only one type of specific amine compound may be used, or two or more types 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 further contain an infrared absorbing agent.
- an infrared absorbing agent for example, in the case of forming an infrared transmission filter using the coloring composition of the present invention, the wavelength of light transmitted through the film obtained by containing an infrared absorbing agent in the coloring composition is shifted to a longer wavelength side.
- the infrared absorbing agent is preferably a compound having a maximum absorption wavelength on the longer wavelength side than the wavelength of 700 nm.
- the infrared absorbing agent is preferably a compound having a maximum absorption wavelength in the range of 700 nm to 1800 nm.
- the ratio A 1 /A 2 between the absorbance A 1 at a wavelength of 500 nm and the absorbance A 2 at the maximum absorption wavelength of the infrared absorbent is preferably 0.08 or less, more preferably 0.04 or less.
- infrared absorbers examples include pyrrolopyrrole compounds, cyanine compounds, squarylium compounds, phthalocyanine compounds, naphthalocyanine compounds, quaterrylene compounds, merocyanine compounds, croconium compounds, oxonol compounds, iminium compounds, dithiol compounds, triarylmethane compounds, pyrromethene compounds, and azomethine. compounds, anthraquinone compounds, dibenzofuranone compounds, dithiolene metal complexes, metal oxides, metal borides, and the like.
- pyrrolopyrrole compound compounds described in paragraph numbers 0016 to 0058 of JP-A-2009-263614, compounds described in paragraph numbers 0037-0052 of JP-A-2011-068731, WO 2015/166873 Compounds described in Paragraph Nos. 0010 to 0033 and the like.
- examples of the squarylium compound include compounds described in paragraph numbers 0044 to 0049 of JP-A-2011-208101, compounds described in paragraph numbers 0060 to 0061 of Japanese Patent No. 6065169, and paragraph number 0040 of WO 2016/181987.
- Examples of croconium compounds include compounds described in JP-A-2017-082029.
- As the iminium compound for example, compounds described in JP-A-2008-528706, compounds described in JP-A-2012-012399, compounds described in JP-A-2007-092060, International Publication No. 2018/043564 and the compounds described in paragraphs 0048 to 0063 of.
- Examples of the phthalocyanine compound include compounds described in paragraph number 0093 of JP-A-2012-077153, oxytitanium phthalocyanine described in JP-A-2006-343631, and paragraph numbers 0013 to 0029 of JP-A-2013-195480. compounds, vanadium phthalocyanine compounds described in Japanese Patent No. 6081771, vanadium phthalocyanine compounds described in International Publication No. 2020/071486, and phthalocyanine compounds described in International Publication No. 2020/071470. Examples of naphthalocyanine compounds include compounds described in paragraph number 0093 of JP-A-2012-077153. Dithiolene metal complexes include compounds described in Japanese Patent No. 5733804.
- metal oxides include indium tin oxide, antimony tin oxide, zinc oxide, Al-doped zinc oxide, fluorine-doped tin dioxide, niobium-doped titanium dioxide, and tungsten oxide.
- metal borides include lanthanum boride.
- Commercially available lanthanum boride products include LaB 6 -F (manufactured by Nippon New Metal Co., Ltd.).
- a metal boride the compound as described in international publication 2017/119394 can also be used.
- commercially available products of indium tin oxide include F-ITO (manufactured by DOWA Hitech Co., Ltd.).
- the infrared absorbing agent the squarylium compound described in JP-A-2017-197437, the squarylium compound described in JP-A-2017-025311, the squarylium compound described in WO 2016/154782, and the patent No. 5884953. No. 6036689, squarylium compounds described in Japanese Patent No. 5810604, squarylium compounds described in paragraphs 0090 to 0107 of International Publication No.
- the content of the infrared absorbing agent in the total solid content of the coloring composition is preferably 1 to 40% by mass.
- the lower limit is more preferably 2% by mass or more, still more preferably 5% by mass or more, and even more preferably 10% by mass or more.
- the upper limit is more preferably 30% by mass or less, and even more preferably 25% by mass or less.
- the coloring composition of the present invention may contain only one type of infrared absorbing agent, or may contain two or more types thereof. When two or more kinds of infrared absorbing agents are included, the total amount thereof is preferably within the above range.
- the coloring composition of the present invention can contain an ultraviolet absorber.
- ultraviolet absorbers include conjugated diene compounds, aminodiene compounds, salicylate compounds, benzophenone compounds, benzotriazole compounds, acrylonitrile compounds, hydroxyphenyltriazine compounds, indole compounds, and triazine compounds. Specific examples of such compounds include paragraph numbers 0038 to 0052 of JP-A-2009-217221, paragraph numbers 0052-0072 of JP-A-2012-208374, and paragraph numbers 0317-0317 of JP-A-2013-068814.
- UV absorber examples include compounds having the following structures.
- examples of commercially available UV absorbers include UV-503 (manufactured by Daito Chemical Co., Ltd.), Tinuvin series and Uvinul series manufactured by BASF, and Sumisorb series manufactured by Sumika Chemtex Co., Ltd. .
- Benzotriazole compounds include the MYUA series manufactured by Miyoshi Oil (Kagaku Kogyo Nippo, February 1, 2016).
- the ultraviolet absorber is a compound described in paragraph numbers 0049 to 0059 of Japanese Patent No.
- the content of the ultraviolet absorber in the total solid content of the coloring composition is preferably 0.01 to 10% by mass, more preferably 0.01 to 5% by mass. Only one type of ultraviolet absorber may be used, or two or more types may be used. When two or more kinds are used, it is preferable that the total amount thereof is within the above range.
- the coloring composition of the present invention can contain a 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 kind of polymerization inhibitor 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 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 thereof is preferably within the above range.
- the coloring composition of the present invention can contain a surfactant.
- a surfactant various surfactants such as fluorine-based 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 a surfactant.
- m represents 1 or 2
- n represents an integer of 1 to 4
- a represents 1 or 2
- X a + is a valent metal ion, primary ammonium ion, Represents secondary ammonium ion, tertiary ammonium ion, quaternary ammonium ion or NH4 + .
- 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 thereof 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, it is preferable that the total amount thereof is 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, for example, described in JP 2012-003225, paragraph number 0183 and later (corresponding US Patent Application Publication No. 2013/0034812, paragraph number 0237), JP 2008-250074 paragraph The descriptions of numbers 0101 to 0104, 0107 to 0109, etc. can be referred to, and the contents thereof are incorporated herein.
- 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 with 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 coloring composition, and if necessary, each component may be appropriately mixed as 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 optical filters such as color filters and infrared transmission filters. Specifically, it can be preferably used as a colored pixel of a color filter. Examples of colored pixels include red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, and yellow pixels. Red pixels, green pixels, and yellow pixels are preferred, and red pixels or green pixels are preferred. is more preferable, and green pixels are even more preferable.
- the film thickness of the film of the present invention can be appropriately adjusted according to the purpose, but is preferably 0.1 to 20 ⁇ m.
- the upper limit of the film thickness is more preferably 10 ⁇ m or less, still more preferably 5 ⁇ m or less, even more preferably 3 ⁇ m or less, and particularly preferably 1.5 ⁇ m or less.
- the lower limit of the film thickness is more preferably 0.2 ⁇ m or more, still more preferably 0.3 ⁇ m or more.
- the film of the invention can be produced through a step of applying the coloring composition of the invention onto a support.
- the film manufacturing method further includes a step of forming a pattern (pixels).
- a method for forming the pattern (pixels) includes a photolithography method and a dry etching method, and the photolithography method is preferable.
- Pattern formation by photolithography includes the steps of forming a colored composition layer on a support using the colored composition of the present invention, a step of patternwise exposing the colored composition layer, and a step of exposing the colored composition layer. forming a pattern (pixels) by developing and removing the exposed portion. If necessary, a step of baking the coloring composition layer (pre-baking step) and a step of baking the developed pattern (pixels) (post-baking step) may be provided.
- the colored composition layer of the present invention is used to form the colored composition layer on 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.
- CCD charge-coupled device
- CMOS complementary metal oxide semiconductor
- 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 light source with a long wavelength of 300 nm or longer 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.
- Pattern formation by a dry etching method is a step of forming a colored composition layer on a support using the colored composition of the present invention, and curing the entire colored composition layer to form a cured product layer; a step of forming a photoresist layer on the cured layer; a step of patternwise exposing the photoresist layer and then developing it to form a resist pattern; and etching the cured layer using the resist pattern as a mask. and dry etching using a gas.
- a mode in which heat treatment after exposure and heat treatment (post-baking treatment) after development are performed is desirable.
- pattern formation by a dry etching method descriptions in paragraphs 0010 to 0067 of JP-A-2013-064993 can be referred to, and the contents thereof are incorporated herein.
- optical filter of the present invention has the film of the present invention as described above.
- Types of optical filters include color filters and infrared transmission filters, and color filters are preferred.
- a color filter preferably has the film of the present invention as its colored pixels.
- the film thickness of the film of the present invention can be appropriately adjusted according to the purpose.
- the film thickness is preferably 20 ⁇ m or less, more preferably 10 ⁇ m or less, even more preferably 5 ⁇ m or less.
- the lower limit of the film thickness is preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more, and even more preferably 0.3 ⁇ m or more.
- the width of pixels included in the optical filter is preferably 0.4 to 10.0 ⁇ m.
- the lower limit is preferably 0.4 ⁇ m or more, more preferably 0.5 ⁇ m or more, and even more preferably 0.6 ⁇ m or more.
- the upper limit is more preferably 5.0 ⁇ m or less, still more preferably 2.0 ⁇ m or less, even more preferably 1.0 ⁇ m or less, and even more preferably 0.8 ⁇ m or less.
- the Young's modulus of the pixel is preferably 0.5 to 20 GPa, more preferably 2.5 to 15 GPa.
- Each pixel included in the optical filter preferably has high flatness.
- the pixel surface roughness Ra is preferably 100 nm or less, more preferably 40 nm or less, and even more preferably 15 nm or less. Although the lower limit is not specified, it is preferably 0.1 nm or more, for example.
- the surface roughness of a pixel can be measured using, for example, AFM (Atomic Force Microscope) Dimension 3100 manufactured by Veeco.
- the contact angle of water on the pixel can be appropriately set to a preferable value, but is typically in the range of 50 to 110°. The contact angle can be measured using, for example, a contact angle meter CV-DT-A type (manufactured by Kyowa Interface Science Co., Ltd.).
- the volume resistance value of the pixel is high.
- the volume resistance value of the pixel is preferably 10 9 ⁇ cm or more, more preferably 10 11 ⁇ cm or more.
- the upper limit is not specified, it is preferably 10 14 ⁇ cm or less, for example.
- the volume resistance value of the pixel can be measured using an ultra-high resistance meter 5410 (manufactured by Advantest).
- a protective layer may be provided on the surface of the film of the present invention.
- the 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 of forming the protective layer include a method of applying a protective layer-forming composition, a chemical vapor deposition method, and a method of adhering 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.
- 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 optical filter may have a structure in which each pixel is embedded in a space partitioned by partition walls, for example, in a grid pattern.
- the solid-state imaging device of the present invention includes the film of the present invention described above.
- the configuration of the solid-state imaging device is not particularly limited as long as it functions as a solid-state imaging device.
- a plurality of photodiodes and transfer electrodes made of polysilicon or the like are provided on the substrate, forming the light-receiving area of a solid-state imaging device (CCD (charge-coupled device) image sensor, CMOS (complementary metal-oxide semiconductor) image sensor, etc.). and a device protective film made of silicon nitride or the like formed on the light shielding film so as to cover the entire surface of the light shielding film and the photodiode light receiving portion. and a color filter on the device protective film.
- CCD charge-coupled device
- CMOS complementary metal-oxide semiconductor
- the color filter may have a structure in which each 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 image display device of the present invention includes the film of the present invention described above.
- 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), etc.
- 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)".
- the present invention can be applied to liquid crystal display devices of various systems described in the above-mentioned "next generation liquid crystal display technology".
- the weight average molecular weight (Mw) of the resin was calculated by GPC (Gel permeation chromatography) measurement under the following measurement conditions.
- Column type Column connecting TOSOH TSKgel Super HZM-H, TOSOH TSKgel Super HZ4000, and TOSOH TSKgel Super HZ2000 Developing solvent: Tetrahydrofuran
- Apparatus name HLC-8220GPC manufactured by Tosoh Corporation Detector: Differential refractometer (RI detector)
- dispersion liquid A mixture of 12.95 parts by mass of a coloring agent, 1.05 parts by mass of a dispersing aid, 24.5 parts by mass of a dispersant, and 61.5 parts by mass of a solvent was passed through a bead mill (0.5 parts by mass of zirconia beads). 1 mm diameter) was used to mix and disperse for 3 hours. Thereafter, using a high-pressure disperser NANO-3000-10 (manufactured by Nippon BEE Co., Ltd.) equipped with a decompression mechanism, dispersion treatment was carried out under conditions of a pressure of 2000 kg/cm 2 and a flow rate of 500 g/min. This dispersing treatment was repeated up to 10 times to obtain a dispersion. Materials shown in the table below were used for each material.
- P-1 C.I. I. Pigment Green 7 (green pigment, copper phthalocyanine pigment)
- P-2 C.I. I. Pigment Green 36 (green pigment, copper phthalocyanine pigment)
- P-3 C.I. I. Pigment Green 58 (green pigment, zinc phthalocyanine pigment)
- P-4 C.I. I. Pigment Green 59 (green pigment, zinc phthalocyanine pigment)
- P-5 C.I. I. Pigment Green 63 (green pigment, aluminum phthalocyanine pigment)
- P-6 C.I. I. Pigment Red 177 (red pigment, anthraquinone pigment)
- P-7 C.I. I.
- Pigment Red 254 (red pigment, diketopyrrolopyrrole pigment)
- P-8 C.I. I. Pigment Red 264 (red pigment, diketopyrrolopyrrole pigment)
- P-9 C.I. I. Pigment Red 272 (red pigment, diketopyrrolopyrrole pigment)
- P-10 C.I. I. Pigment Red 291 (red pigment, diketopyrrolopyrrole pigment)
- P-11 compounds having the following structures (red dyes, perylene dyes)
- P-12 Compounds with the following structures (red dyes, perylene dyes)
- P-13 Compounds with the following structures (red dyes, xanthene dyes)
- P-14 compounds with the following structures (red dyes, xanthene dyes)
- P-15 Compound having the following structure (red dye, tetraazaporphyrin dye)
- P-16 Compounds with the following structures (red pigments, perylene pigments)
- P-17 Lumogen F Orange 240 (manufactured by BASF, red pigment, perylene pigment)
- P-18 C.I. I. Pigment Red 179 (red pigment, perylene pigment)
- P-20 compounds with the following structures (red pigments, xanthene pigments)
- P-21 C.I. I. Pigment Red 81:4 (red pigment, xanthene pigment)
- P-22 C.I. I. Pigment Blue 15:4 (blue pigment, phthalocyanine pigment)
- P-23 C.I. I. Pigment Blue 15:6 (blue pigment, phthalocyanine pigment)
- P-24 C.I. I. Pigment Blue 16 (blue pigment, phthalocyanine pigment)
- P-25 Compound with the following structure (cyan dye, squarylium dye)
- P-26 A compound having the following structure (cyan pigment, triarylmethane pigment)
- P-27 Copolymer (cyan dye) of 40 parts by mass of a compound having the following structure, 25 parts by mass of benzyl methacrylate, 20 parts by mass of methacrylic acid, and N-benzylmaleimide
- P-28 Compound with the following structure (cyan dye, squarylium dye)
- P-29 A compound having the following structure (cyan dye, weight average molecular weight 85000, acid value 1.0 mmol/g). The compound having the structure below was synthesized with reference to JP-A-2016-102191 and WO2019/167589.
- P-30 C.I. I. Pigment Violet 23 (purple pigment, dioxazine pigment)
- P-31 C.I. I. Pigment Yellow 129 (yellow pigment, azomethine pigment)
- P-32 C.I. I. Pigment Yellow 138 (yellow pigment, quinophthalone pigment)
- P-33 C.I. I. Pigment Yellow 139 (yellow pigment, isoindoline pigment)
- P-34 C.I. I. Pigment Yellow 150 (yellow pigment, azo pigment)
- P-35 C.I. I. Pigment Yellow 155 (yellow pigment, azo pigment)
- P-36 C.I. I.
- Pigment Yellow 185 (yellow pigment, isoindoline pigment)
- P-37 C.I. I. Pigment Yellow 215 (yellow pigment, pteridine pigment)
- P-38 C.I. I. Pigment Yellow 231 (yellow pigment)
- P-39 C.I. I. Pigment Yellow 233 (yellow pigment)
- P-40 compound with the following structure (yellow pigment, isoindoline pigment)
- (dispersion aid) Syn-1 a compound having the following structure (pigment derivative) Syn-2: a compound having the following structure (pigment derivative) Syn-3: a compound having the following structure (pigment derivative) Syn-4: a compound having the following structure (pigment derivative) Syn-5: a compound having the following structure (pigment derivative) Syn-6: a compound having the following structure (pigment derivative) Syn-7: polyethyleneimine (Epomin SP-006, manufactured by Nippon Shokubai Co., Ltd.) Syn-8: ADEKA STAB LA-52 (manufactured by ADEKA Co., Ltd.)
- (dispersant) B-1 A 20% by mass propylene glycol monomethyl ether acetate (PGMEA) solution of resin B-1 synthesized by the following method. 108 parts by mass of 1-thioglycerol, 174 parts by mass of pyromellitic anhydride, 650 parts by mass of propylene glycol monomethyl ether acetate (PGMEA), and 0.2 parts by mass of monobutyltin oxide as a catalyst were charged into a reaction vessel, and the atmospheric gas was nitrogen gas. and then reacted at 120° C. for 5 hours (first step). It was confirmed by acid value measurement that 95% or more of the acid anhydride was half-esterified.
- PGMEA propylene glycol monomethyl ether acetate
- a 20% by mass PGMEA solution of resin B-2 synthesized by the following method 50 parts by mass of methyl methacrylate, 30 parts by mass of n-butyl methacrylate, 20 parts by mass of (3-ethyloxetan-3-yl)methyl methacrylate, and 45.4 parts by mass of propylene glycol monomethyl ether acetate (PGMEA) were charged into a reaction vessel, and the atmosphere was The gas was replaced with nitrogen gas. Heat the inside of the reaction vessel to 70° C., add 6 parts by mass of 3-mercapto-1,2-propanediol, add 0.12 parts by mass of AIBN (azobisisobutyronitrile), and react for 12 hours.
- PGMEA propylene glycol monomethyl ether acetate
- Resin B-2 having the following structure with an acid value of 43 mgKOH/g and a weight average molecular weight of 9,000.
- B-3 20% by mass of a 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 16000, acid value 67 mgKOH/g) PGMEA solution.
- B-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 24000, acid value 58.4 mgKOH / g) of 20 mass % PGMEA solution.
- B-5 20% by mass of a 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, acid value 77 mgKOH/g) PGMEA solution.
- Dispersions G-1 to G-27 Dispersions G-1 to G-27 as described above
- Dispersions R-1 to R-36 Dispersions R-1 to R-36 as described above
- Dispersions IR-1 to IR-9 Dispersions IR-1 to IR-9 as described above
- Dispersions Y-1 to Y-10 Dispersions Y-1 to Y-10 described above
- Dispersion cR-1 Dispersion cR-1 described above
- M-1 a compound having the following structure
- M-2 a compound having the following structure
- M-3 KAYARAD DPHA (manufactured by Nippon Kayaku Co., Ltd.)
- M-4 a compound having the following structure
- I-1 Irgacure OXE02 (manufactured by BASF, oxime compound)
- I-2 to I-6 compounds having the following structures
- binder B-6 20% 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: 11,000; acid value: 69.2 mgKOH/g)
- B-7 A 20% 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: 21000)
- B-10 A 20% by mass PGMEA solution of a resin synthesized by the following method An appropriate amount of nitrogen is flowed into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to create a nitrogen atmosphere, and 280 parts by mass of PGMEA is added and stirred. Heat to 80°C. Next, 38 parts by mass of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.
- a solution prepared by dissolving 289 parts by mass of a mixture of 1.0 2,6 ]decane-9-yl acrylate (content ratio is 1:1) in 125 parts by mass of PGMEA was added dropwise over about 5 hours using a dropping pump.
- a solution prepared by dissolving 33 parts by mass of 2,2-azobis(2,4-dimethylvaleronitrile) as a polymerization initiator in 235 parts by mass of PGMEA was dropped into the flask over about 6 hours using another dropping pump. After completion of dropping, the mixture was kept at the same temperature for 4 hours and then cooled to room temperature to synthesize a resin having the following structure (weight average molecular weight: 9200, dispersity: 2.08, acid value: 77 mgKOH/g).
- B-11 Solution obtained by adding PGMEA to EPICLON N-695 (manufactured by DIC Corporation, a resin having an epoxy group) to adjust the solid content concentration to 20% by mass
- B-12 EHPE3150 (manufactured by Daicel Co., Ltd., 2 ,2'-Bis(hydroxymethyl)-1-butanol 1,2-epoxy-4-(2-oxiranyl)cyclohexane adduct) and PGMEA added to adjust the solid content concentration to 20% by mass
- B-13 A solution obtained by adding PGMEA to jER1031S (manufactured by Mitsubishi Chemical Corporation, a resin having an epoxy group) to adjust the solid content concentration to 20% by mass
- B-14 BATG (manufactured by Showa Denko Co., Ltd., a resin having an epoxy group ) in which PGMEA was added to adjust the solid content concentration to 20% by mass
- B-15 20 wt% PGMEA solution of a resin having the following structure (numerical values attached to the main chain are molar ratios; weight average molecular weight: 11,000)
- Ad-2 Sumisorb 200 (manufactured by Sumika Chemtex Co., Ltd., 2-(2-hydroxy-5-methylphenyl)benzotriazole, UV absorber)
- Ad-3 a compound having the following structure (ultraviolet absorber)
- Ad-4 Sumisorb 130 (manufactured by Sumika Chemtex Co., Ltd., 2-hydroxy-4-n-octoxybenzophenone, UV absorber)
- Ad-5 EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd., 4,4'-bis(diethylamino)benzophenone, sensitizer)
- Viscosity fluctuation rate (%)
- the underlayer composition was applied by spin coating, then heated at 100° C. for 2 minutes using a hot plate, and then heated to 230° C. using a hot plate. C. for 2 minutes to form an underlayer having a thickness of 10 nm.
- the details of the underlayer composition will be described later.
- the coloring compositions of Examples and Comparative Examples are applied by a spin coating method so that the film thickness after forming the film is 0.5 ⁇ m, and then a hot plate is applied. and heated at 100° C. for 2 minutes.
- i-line stepper exposure apparatus FPA-3000i5+ manufactured by Canon Inc.
- exposure was performed at an exposure amount of 200 mJ/cm 2 through a mask having an island pattern of 1.0 ⁇ m.
- the silicon wafer was stored for 30 minutes in an environment with a temperature of 23° C. and a humidity of 50%, and then puddle development was performed at 23° C. for 60 seconds using a 0.3 mass % aqueous solution of tetramethylammonium hydroxide (TMAH). .
- TMAH tetramethylammonium hydroxide
- the substrate was rinsed with a spin shower, washed with pure water, and then heated at 220° C. for 5 minutes using a hot plate to form island pattern pixels.
- the underlayer composition was produced by mixing the following raw materials.
- Resin A 0.7 parts by mass
- Surfactant A 0.8 parts by mass
- Propylene glycol monomethyl ether acetate (PGMEA) 98.5 parts by mass
- Surfactant A 0.2% by mass PGMEA solution of a compound having the following structure (weight average molecular weight: 14,000; % values indicating the ratio of repeating units are mol %; fluorosurfactant)
- the colored compositions of the examples had good storage stability and were able to form films with excellent moisture resistance.
- a coloring agent C.I. I. Pigment Yellow 155 and C.I. I. Pigment Yellow 129 or C.I. I.
- Pigment Yellow 150 was used in combination, storage stability could be further improved.
- Example 1 the same results as in Example 1 are obtained even when the surfactant is omitted. Moreover, even when the polymerization inhibitor is omitted in Example 1, the same results as in Example 1 are obtained.
- optical filters By using the films obtained from the colored compositions of Examples, optical filters, solid-state imaging devices, and image display devices with excellent moisture resistance can be obtained.
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Abstract
Description
上記着色剤はカラーインデックスピグメントイエロー155を含み、
上記着色組成物の全固形分中におけるカラーインデックスピグメントイエロー155の含有量が16質量%以上である、着色組成物。
<2> 上記着色剤は、カラーインデックスピグメントイエロー155以外の黄色着色剤を含む、<1>に記載の着色組成物。
<3> 上記カラーインデックスピグメントイエロー155以外の黄色着色剤は、カラーインデックスピグメントイエロー129、カラーインデックスピグメントイエロー150から選ばれる少なくとも1種である、<2>に記載の着色組成物。
<4> 上記着色剤中におけるカラーインデックスピグメントイエロー155の含有量が40質量%以上である、<1>~<3>のいずれか1つに記載の着色組成物。
<5> 着色剤と、樹脂とを含む着色組成物であって、
上記着色剤は式(1)で表される化合物を含み、
上記着色組成物の全固形分中における式(1)で表される化合物の含有量が16質量%以上である、着色組成物;
<6> 上記着色剤は、緑色着色剤および赤色着色剤から選ばれる少なくとも1種を含む、<1>~<5>のいずれか1つに記載の着色組成物。
<7> 上記緑色着色剤は、フタロシアニン顔料を含む、<6>に記載の着色組成物。
<8> 上記緑色着色剤は、亜鉛フタロシアニン顔料を含む、<6>に記載の着色組成物。
<9> 上記緑色着色剤は、カラーインデックスピグメントグリーン7、カラーインデックスピグメントグリーン58およびカラーインデックスピグメントグリーン59から選ばれる少なくとも1種を含む、<6>に記載の着色組成物。
<10> 上記着色組成物の全固形分中における上記着色剤の含有量が45質量%以上である、<1>~<9>のいずれか1つに記載の着色組成物。
<11> 上記樹脂は、環状エーテル基を有する樹脂を含む、<1>~<10>のいずれか1つに記載の着色組成物。
<12> 更に、重合性化合物と、光重合開始剤とを含む、<1>~<11>のいずれか1つに記載の着色組成物。
<13> カラーフィルタ用である、<1>~<12>のいずれか1つに記載の着色組成物。
<14> <1>~<13>のいずれか1つに記載の着色組成物から得られる膜。
<15> <14>に記載の膜を有する光学フィルタ。
<16> <14>に記載の膜を有する固体撮像素子。
<17> <14>に記載の膜を有する画像表示装置。
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、樹脂とを含む着色組成物であって、
上記着色剤はカラーインデックスピグメントイエロー155を含み、
上記着色組成物の全固形分中におけるカラーインデックスピグメントイエロー155の含有量が16質量%以上であることを特徴とする。
着色剤と、樹脂とを含む着色組成物であって、
上記着色剤は式(1)で表される化合物を含み、
上記着色組成物の全固形分中における式(1)で表される化合物の含有量が16質量%以上であることを特徴とする。
(1):波長400~640nmの範囲における透過率の最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)であり、波長800~1500nmの範囲における透過率の最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)であるフィルタ。
(2):波長400~750nmの範囲における透過率の最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)であり、波長900~1500nmの範囲における透過率の最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)であるフィルタ。
(3):波長400~830nmの範囲における透過率の最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)であり、波長1000~1500nmの範囲における透過率の最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)であるフィルタ。
(4):波長400~950nmの範囲における透過率の最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)であり、波長1100~1500nmの範囲における透過率の最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)であるフィルタ。
(5):波長400~1050nmの範囲における透過率の最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)であり、波長1200~1500nmの範囲における透過率の最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)であるフィルタ。
(特定着色剤)
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おいて、着色剤にはC.I.(カラーインデックス)ピグメントイエロー155、または、式(1)で表される化合物を含むものが用いられる。以下、C.I.ピグメントイエロー155と式(1)で表される化合物とを合わせて、特定着色剤ともいう。
アルケニル基の炭素数は、2~30が好ましく、2~20がより好ましく、2~10が更に好ましく、2~5がより一層好ましく、2または3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いが、直鎖または分岐であることが好ましく、直鎖であることがより好ましい。
アルキニル基の炭素数は、2~30が好ましく、2~20がより好ましく、2~10が更に好ましく、2~5がより一層好ましく、2または3が特に好ましい。アルキニル基は、直鎖、分岐、環状のいずれでもよいが、直鎖または分岐であることが好ましく、直鎖であることがより好ましい。
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。
本発明の着色組成物に含まれる着色剤は、上記特定着色剤以外の着色剤(他の着色剤)をさらに含有することができる。併用する他の着色剤としては、緑色着色剤、赤色着色剤、黄色着色剤、紫色着色剤、青色着色剤、シアン色着色剤、オレンジ色着色剤などが挙げられる。他の着色剤は、黄色着色剤、緑色着色剤および赤色着色剤から選ばれる少なくとも1種であることが好ましく、緑色着色剤および赤色着色剤から選ばれる少なくとも1種であることがより好ましく、緑色着色剤であることが更に好ましい。他の着色剤は、顔料であってもよく、染料であってもよいが、顔料であることが好ましい。
(1)黄色着色剤、青色着色剤、紫色着色剤および赤色着色剤を含有する態様。
(2)黄色着色剤、緑色着色剤、紫色着色剤および赤色着色剤を含有する態様。
(3)黄色着色剤、シアン色着色剤、紫色着色剤および赤色着色剤を含有する態様。
(4)黄色着色剤、青色着色剤および赤色着色剤を含有する態様。
(5)黄色着色剤、緑色着色剤および赤色着色剤を含有する態様。
(6)黄色着色剤、シアン色着色剤および赤色着色剤を含有する態様。
(7)黄色着色剤、紫色着色剤および赤色着色剤を含有する態様。
また、特定着色剤以外の黄色着色剤の含有量は特定着色剤の100質量部に対して1~100質量部であることが好ましい。上限は90質量部以下であることがより好ましく、80質量部以下であることが更に好ましい。下限は10質量部以上であることがより好ましく、50質量部以上であることが更に好ましい。
また、特定着色剤以外の黄色着色剤がC.I.ピグメントイエロー129およびC.I.ピグメントイエロー150から選ばれる少なくとも1種を含む場合、C.I.ピグメントイエロー129とC.I.ピグメントイエロー150の含有量は特定着色剤の100質量部に対して1~100質量部であることが好ましい。上限は90質量部以下であることがより好ましく、80質量部以下であることが更に好ましい。下限は10質量部以上であることがより好ましく、50質量部以上であることが更に好ましい。
黄色着色剤と緑色着色剤との質量比は、黄色着色剤:緑色着色剤=10:90~70:30であることが好ましく、20:80~60:40であることがより好ましく、30:70~50:50であることが更に好ましい。
特定着色剤の含有量は、緑色着色剤の100質量部に対して30~100質量部であることが好ましい。下限は、40質量部以上であることがより好ましく、50質量部以上であることが更に好ましい。上限は、90質量部以下であることがより好ましく、80質量部以下であることが更に好ましい。
黄色着色剤と赤色着色剤との質量比は、黄色着色剤:赤色着色剤=70:30~10:90であることが好ましく、60:40~20:80であることがより好ましく、50:50~30:70であることが更に好ましい。
また、特定着色剤の含有量は、赤色着色剤の100質量部に対して20~90質量部であることが好ましい。下限は、30質量部以上であることがより好ましく、40質量部以上であることが更に好ましい。上限は、80質量部以下であることがより好ましく、70質量部以下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有する。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。
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。
本発明の着色組成物は、重合性化合物を含有することが好ましい。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。
本発明の着色組成物は光重合開始剤を含有することが好ましい。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し、
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。
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、溶剤を含有することが好ましい。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、1分子中に塩基性基を3個以上含み、アミン価が2.7mmol/g以上で、分子量が100以上の化合物(以下特定アミン化合物ともいう)を含有することもできる。
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、赤外線吸収剤をさらに含有することができる。例えば、本発明の着色組成物を用いて赤外線透過フィルタを形成する場合においては、着色組成物中に赤外線吸収剤を含有させることで得られる膜について透過させる光の波長をより長波長側にシフトさせることができる。赤外線吸収剤は、極大吸収波長を波長700nmよりも長波長側に有する化合物であることが好ましい。赤外線吸収剤は波長700nmを超え1800nm以下の範囲に極大吸収波長を有する化合物であることが好ましい。また、赤外線吸収剤の波長500nmにおける吸光度A1と極大吸収波長における吸光度A2との比率A1/A2は、0.08以下であることが好ましく、0.04以下であることがより好ましい。
本発明の着色組成物は、紫外線吸収剤を含有することができる。紫外線吸収剤としては、共役ジエン化合物、アミノジエン化合物、サリシレート化合物、ベンゾフェノン化合物、ベンゾトリアゾール化合物、アクリロニトリル化合物、ヒドロキシフェニルトリアジン化合物、インドール化合物、トリアジン化合物などが挙げられる。このような化合物の具体例としては、特開2009-217221号公報の段落番号0038~0052、特開2012-208374号公報の段落番号0052~0072、特開2013-068814号公報の段落番号0317~0334、特開2016-162946号公報の段落番号0061~0080に記載された化合物が挙げられ、これらの内容は本明細書に組み込まれる。紫外線吸収剤の具体例としては、下記構造の化合物などが挙げられる。紫外線吸収剤の市販品としては、例えば、UV-503(大東化学(株)製)、BASF社製のTinuvinシリーズ、Uvinul(ユビナール)シリーズ、住化ケムテックス(株)製のSumisorbシリーズなどが挙げられる。また、ベンゾトリアゾール化合物としては、ミヨシ油脂製のMYUAシリーズ(化学工業日報、2016年2月1日)が挙げられる。また、紫外線吸収剤は、特許第6268967号公報の段落番号0049~0059に記載された化合物、国際公開第2016/181987号の段落番号0059~0076に記載された化合物、国際公開第2020/137819号に記載されたチオアリール基置換ベンゾトリアゾール型紫外線吸収剤を用いることもできる。
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、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、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、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、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、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、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、カラーフィルタや赤外線透過フィルタなどの光学フィルタなどに用いることができる。特に具体的には、カラーフィルタの着色画素として好ましく用いることができる。着色画素としては、赤色画素、緑色画素、青色画素、マゼンタ色画素、シアン色画素、黄色画素などが挙げられ、赤色画素、緑色画素および黄色画素であることが好ましく、赤色画素または緑色画素であることがより好ましく、緑色画素であることが更に好ましい。
本発明の膜は、本発明の着色組成物を支持体に塗布する工程を経て製造できる。膜の製造方法においては、更にパターン(画素)を形成する工程を含むことが好ましい。パターン(画素)の形成方法としては、フォトリソグラフィ法、ドライエッチング法が挙げられ、フォトリソグラフィ法が好ましい。
本発明の光学フィルタは、上述した本発明の膜を有する。光学フィルタの種類としては、カラーフィルタおよび赤外線透過フィルタなどが挙げられ、カラーフィルタであることが好ましい。カラーフィルタは、その着色画素として本発明の膜を有することが好ましい。
本発明の固体撮像素子は、上述した本発明の膜を含む。固体撮像素子の構成としては、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。
本発明の画像表示装置は、上述した本発明の膜を含む。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。
樹脂の重量平均分子量(Mw)は、下記測定条件の下、GPC(Gel permeation chromatography)測定により算出した。
カラムの種類:TOSOH TSKgel Super HZM-Hと、TOSOH TSKgel Super HZ4000と、TOSOH TSKgel Super HZ2000とを連結したカラム
展開溶媒:テトラヒドロフラン
カラム温度:40℃
流量(サンプル注入量):1.0μL(サンプル濃度0.1質量%)
装置名:東ソー(株)製 HLC-8220GPC
検出器:示差屈折計(RI検出器)
着色剤を12.95質量部と、分散助剤を1.05質量部と、分散剤を24.5質量部と、溶剤を61.5質量部との混合液を、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。その後、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/cm2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回まで繰り返して、分散液を得た。各素材はそれぞれ下記表に示す素材を用いた。
P-1: C.I.ピグメントグリーン7(緑色顔料、銅フタロシアニン顔料)
P-2: C.I.ピグメントグリーン36(緑色顔料、銅フタロシアニン顔料)
P-3: C.I.ピグメントグリーン58(緑色顔料、亜鉛フタロシアニン顔料)
P-4: C.I.ピグメントグリーン59(緑色顔料、亜鉛フタロシアニン顔料)
P-5: C.I.ピグメントグリーン63(緑色顔料、アルミニウムフタロシアニン顔料)
P-6: C.I.ピグメントレッド177(赤色顔料、アントラキノン顔料)
P-7: C.I.ピグメントレッド254(赤色顔料、ジケトピロロピロール顔料)
P-8: C.I.ピグメントレッド264(赤色顔料、ジケトピロロピロール顔料)
P-9: C.I.ピグメントレッド272(赤色顔料、ジケトピロロピロール顔料)
P-10: C.I.ピグメントレッド291(赤色顔料、ジケトピロロピロール顔料)
P-18: C.I.ピグメントレッド179(赤色顔料、ペリレン顔料)
P-22: C.I.ピグメントブルー15:4(青色顔料、フタロシアニン顔料)
P-23: C.I.ピグメントブルー15:6(青色顔料、フタロシアニン顔料)
P-24: C.I.ピグメントブルー16(青色顔料、フタロシアニン顔料)
P-31: C.I.ピグメントイエロー129(黄色顔料、アゾメチン顔料)
P-32: C.I.ピグメントイエロー138(黄色顔料、キノフタロン顔料)
P-33: C.I.ピグメントイエロー139(黄色顔料、イソインドリン顔料)
P-34: C.I.ピグメントイエロー150(黄色顔料、アゾ顔料)
P-35: C.I.ピグメントイエロー155(黄色顔料、アゾ顔料)
P-36: C.I.ピグメントイエロー185(黄色顔料、イソインドリン顔料)
P-37: C.I.ピグメントイエロー215(黄色顔料、プテリジン顔料)
P-38: C.I.ピグメントイエロー231(黄色顔料)
P-39: C.I.ピグメントイエロー233(黄色顔料)
Syn-1:下記構造の化合物(顔料誘導体)
Syn-8:アデカスタブLA-52((株)ADEKA製)
B-1:以下の方法で合成した樹脂B-1の20質量%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)溶液。
1-チオグリセロール108質量部、ピロメリット酸無水物174質量部、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)650質量部、触媒としてモノブチルスズオキシド0.2質量部を反応容器に仕込み、雰囲気ガスを窒素ガスで置換した後、120℃で5時間反応させた(第一工程)。酸価の測定で95%以上の酸無水物がハーフエステル化していることを確認した。次に、第一工程で得られた化合物を固形分換算で160質量部、2-ヒドロキシプロピルメタクリレート200質量部、エチルアクリレート200質量部、t-ブチルアクリレート150質量部、2-メトキシエチルアクリレート200質量部、メチルアクリレート200質量部、メタクリル酸50質量部、PGMEA663質量部を反応容器に仕込み、反応容器内を80℃に加熱して、2,2’-アゾビス(2,4-ジメチルバレロニトリル)1.2質量部を添加し、12時間反応させた(第二工程)。固形分測定により95%が反応したことを確認した。最後に、第二工程で得られた化合物の50質量%PGMEA溶液500質量部、2-メタクリロイルオキシエチルイソシアネート(MOI)27.0質量部、ヒドロキノン0.1質量部を反応容器に仕込み、イソシアネート基に基づく2270cm-1のピークの消失を確認するまで反応を行った(第三工程)。ピーク消失の確認後、反応溶液を冷却して、酸価68mgKOH/g、エチレン性不飽和結合基価0.62mmol/g、重量平均分子量13000の下記構造の樹脂B-1(酸基を有する樹脂)を得た。
メチルメタクリレート50質量部、n-ブチルメタクリレート30質量部、(3-エチルオキセタン-3-イル)メチルメタクリレート20質量部、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)45.4質量部を反応容器に仕込み、雰囲気ガスを窒素ガスで置換した。反応容器内を70℃に加熱して、3-メルカプト-1,2-プロパンジオール6質量部を添加して、さらにAIBN(アゾビスイソブチロニトリル)0.12質量部を加え、12時間反応させた。固形分測定により95%が反応したことを確認した。次に、ピロメリット酸無水物9.7質量部、PGMEA70.3質量部、触媒としてDBU(1,8-ジアザビシクロ-[5.4.0]-7-ウンデセン)0.20質量部を追加し、120℃で7時間反応させた。酸価の測定で98%以上の酸無水物がハーフエステル化していることを確認して反応を終了させ、酸価43mgKOH/g、重量平均分子量9000の下記構造の樹脂B-2を得た。
S-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)
S-2:プロピレングリコールモノメチルエーテル
S-3:シクロヘキサノン
S-4:シクロペンタノン
S-5:ジアセトンアルコール
S-6:アニソール
各素材を、以下に示す処方で混合し、孔径0.45μmのナイロン製フィルタ(日本ポール(株)製)でろ過して各着色組成物を製造した。下記表において、着色組成物の全固形分中における着色剤の含有量の値を「着色剤濃度」の欄に記載し、着色組成物の全固形分中におけるC.I.ピグメントイエロー155の含有量の値を「PY155濃度」の欄に記載する。
下記表に記載の分散液 ・・・76.4質量部
下記表に記載の重合性化合物 ・・・1.4質量部
下記表に記載のバインダー(20%PGMEA溶液) ・・・5.1質量部
下記表に記載の光重合開始剤 ・・・0.7質量部
下記表に記載の界面活性剤 ・・・0.02質量部
下記表に記載の重合禁止剤 ・・・0.0002質量部
下記表に記載の添加剤 ・・・0.36質量部
下記表に記載の溶剤 ・・・15.9質量部
下記表に記載の分散液 ・・・62.5質量部
下記表に記載の重合性化合物 ・・・1.4質量部
下記表に記載のバインダー(20%PGMEA溶液) ・・・18.2質量部
下記表に記載の光重合開始剤 ・・・0.7質量部
下記表に記載の界面活性剤 ・・・0.02質量部
下記表に記載の重合禁止剤 ・・・0.0002質量部
下記表に記載の添加剤 ・・・0.36質量部
下記表に記載の溶剤 ・・・16.7質量部
下記表に記載の分散液 ・・・48.6質量部
下記表に記載の重合性化合物 ・・・1.4質量部
下記表に記載のバインダー(20%PGMEA溶液) ・・・26.8質量部
下記表に記載の光重合開始剤 ・・・0.7質量部
下記表に記載の界面活性剤 ・・・0.02質量部
下記表に記載の重合禁止剤 ・・・0.0002質量部
下記表に記載の添加剤 ・・・0.36質量部
下記表に記載の溶剤 ・・・22.0質量部
分散液G-1~G-27:上述した分散液G-1~G-27
分散液R-1~R-36:上述した分散液R-1~R-36
分散液IR-1~IR-9:上述した分散液IR-1~IR-9
分散液Y-1~Y-10:上述した分散液Y-1~Y-10
分散液cR-1:上述した分散液cR-1
冷却管と撹拌機を備えたフラスコに、PGMEA100質量部を仕込んで窒素置換した。80℃に加熱して、同温度で、PGMEA100質量部、メタクリル酸15質量部、スチレン15質量部、ベンジルメタクリレート5質量部、2-ヒドロキシエチルメタクリレート15質量部、2-エチルヘキシルメタクリレート23質量部、N-フェニルマレイミド12質量部、こはく酸モノ(2-アクリロイルオキシエチル)15質量部及び2,2’-アゾビス(2,4-ジメチルバレロニトリル)6質量部の混合溶液を1時間かけて滴下し、この温度を保持して2時間重合した。その後、反応溶液の温度を100℃に昇温させ、さらに1時間重合し、樹脂(重量平均分子量12000、酸価137mgKOH/g)を合成した。
冷却管と撹拌機を備えたフラスコに、PGMEA100質量部を仕込んで窒素置換した。80℃に加熱して、同温度で、PGMEA100質量部、メタクリル酸7質量部、スチレン15質量部、ベンジルメタクリレート10質量部、2-ヒドロキシエチルメタクリレート20質量部、2-エチルヘキシルメタクリレート28質量部、N-フェニルマレイミド15質量部、こはく酸モノ(2-アクリロイルオキシエチル)5質量部及び2,2’-アゾビス(2,4-ジメチルバレロニトリル)4質量部の混合溶液を1時間かけて滴下し、この温度を保持して2時間重合した。その後、反応溶液の温度を100℃に昇温させ、さらに1時間重合し、樹脂(重量平均分子量18500、酸価59mgKOH/g)を合成した。
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て窒素雰囲気とし、PGMEA280質量部を入れ、撹拌しながら80℃まで加熱した。次いで、フラスコ内に、アクリル酸38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(含有率は1:1)289質量部をPGMEA125質量部に溶解した溶液を滴下ポンプを用いて約5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)33質量部をPGMEA235質量部に溶解した溶液を別の滴下ポンプを用いて約6時間かけてフラスコ内に滴下した。滴下終了後、4時間同温度で保持した後、室温まで冷却して、下記構造の樹脂(重量平均分子量9200、分散度2.08、酸価77mgKOH/g)を合成した。
B-12:EHPE3150((株)ダイセル製、2,2’-ビス(ヒドロキシメチル)-1-ブタノールの1,2-エポキシ-4-(2-オキシラニル)シクロヘキサン付加物)にPGMEAを加えて固形分濃度を20質量%に調整した溶液
B-13:jER1031S(三菱ケミカル(株)製、エポキシ基を有する樹脂)にPGMEAを加えて固形分濃度を20質量%に調整した溶液
B-14:BATG(昭和電工(株)製、エポキシ基を有する樹脂)にPGMEAを加えて固形分濃度を20質量%に調整した溶液
W-1:KF-6000(信越化学工業(株)製、シリコーン系界面活性剤)
W-2:KF-6001(信越化学工業(株)製、シリコーン系界面活性剤)
W-3:PolyFox PF6320(OMNOVA社製、フッ素系界面活性剤)
W-4:メガファックF-554(DIC(株)製、フッ素系界面活性剤)
W-5:FZ-2122(ダウ・東レ(株)、シリコーン系界面活性剤)
W-6:SH8400(ダウ・東レ(株)、シリコーン系界面活性剤)
Ad-1:p-メトキシフェノール
Ad-2:Sumisorb 200(住化ケムテックス(株)製、2-(2-ヒドロキシ-5-メチルフェニル)ベンゾトリアゾール、紫外線吸収剤)
Ad-3:下記構造の化合物(紫外線吸収剤)
Ad-5:EABーF(保土ヶ谷化学工業(株)製、4,4’ービス(ジエチルアミノ)ベンゾフェノン、増感剤)
S-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)
S-2:プロピレングリコールモノメチルエーテル
S-3:シクロヘキサノン
S-4:シクロペンタノン
S-5:ジアセトンアルコール
S-6:アニソール
製造直後の着色組成物の初期粘度(V0)を、東機産業(株)製「RE-85L」にて測定した。初期粘度(V0)を測定後、着色組成物を5℃の温度にて、9か月静置したのち、静置後の粘度(V1)を測定した。下記式から静置後の着色組成物の粘度変動率(%)を算出し、以下の基準により保存安定性を評価した。着色組成物の粘度は25℃に温度調整を施した状態で測定した。
粘度変動率(%)=|(静置後の粘度(V1)-初期粘度(V0)|/初期粘度(V0))×100
5:粘度変動率が5%以下である
4:粘度変動率が5%を超え10%以下である
3:粘度変動率が10%を超え30%以下である
2:粘度変動率が30%を超え50%以下である
1:粘度変動率が50%を超える
直径8インチ(20.32cm)のシリコンウエハ上に、下地層用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用いて、100℃で2分間加熱し、次いで、ホットプレートを用いて230℃で2分間加熱して膜厚10nmの下地層を形成した。下地層用組成物の詳細については後述する。
次に、下地層を形成したシリコンウエハ上に、実施例および比較例の着色組成物を、製膜後の膜厚が0.5μmになるようにスピンコート法で塗布し、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+(Canon(株)製)を用い、1.0μmのアイランドパターンを有するマスクを介して、200mJ/cm2の露光量で露光した。次いで、シリコンウエハを温度23℃、湿度50%の環境下にて30分間保管した後、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、さらに純水にて水洗した後に、ホットプレートを用いて220℃で5分間加熱してアイランドパターンの画素を形成した。
アイランドパターンの画素が形成されたシリコンウエハについて、温度23℃、湿度50%の環境下にてプロピレングリコールモノメチルエーテルアセテートを5分間パドルした後に、画素上のプロピレングリコールモノメチルエーテルアセテートをスピンドライにより除去し、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秒間パドルした。その後、スピンシャワーにてリンスを行い、さらに純水にて水洗した後に、ホットプレートを用いて220℃で5分間加熱した。
上記処理後のアイランドパターンの画素が形成されたシリコンウエハについて、恒温恒湿試験(温度85℃、湿度95%の環境下で1000時間の保持)を実施し、任意に選択した30個の画素を走査電子顕微鏡(SEM)で観察して画素中の異物の発生の有無を確認し、以下の基準で耐湿性を評価した。
5:30個の画素の全てで異物の発生は見られなかった。
4:異物が発生した画素が1~3個であった。
3:異物が発生した画素が4~10個であった。
2:異物が発生した画素が11~20個であった。
1:異物が発生した画素が21個以上であった。
樹脂A ・・・0.7質量部
界面活性剤A ・・・0.8質量部
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) ・・・98.5質量部
樹脂A:サイクロマーP(ACA)230AA ((株)ダイセル製、酸価=30mgKOH/g、重量平均分子量15000、54質量%PGME溶液)
界面活性剤A:下記構造の化合物(重量平均分子量14000、繰り返し単位の割合を示す%の数値はモル%である。フッ素系界面活性剤)の0.2質量%PGMEA溶液
実施例1において、界面活性剤を除いた場合においても、実施例1と同様の結果が得られる。また、実施例1において、重合禁止剤を除いた場合においても、実施例1と同様の結果が得られる。
Claims (17)
- 着色剤と、樹脂とを含む着色組成物であって、
前記着色剤はカラーインデックスピグメントイエロー155を含み、
前記着色組成物の全固形分中におけるカラーインデックスピグメントイエロー155の含有量が16質量%以上である、着色組成物。 - 前記着色剤は、カラーインデックスピグメントイエロー155以外の黄色着色剤を含む、請求項1に記載の着色組成物。
- 前記カラーインデックスピグメントイエロー155以外の黄色着色剤は、カラーインデックスピグメントイエロー129、カラーインデックスピグメントイエロー150から選ばれる少なくとも1種である、請求項2に記載の着色組成物。
- 前記着色剤中におけるカラーインデックスピグメントイエロー155の含有量が40質量%以上である、請求項1~3のいずれか1項に記載の着色組成物。
- 前記着色剤は、緑色着色剤および赤色着色剤から選ばれる少なくとも1種を含む、請求項1~5のいずれか1項に記載の着色組成物。
- 前記緑色着色剤は、フタロシアニン顔料を含む、請求項6に記載の着色組成物。
- 前記緑色着色剤は、亜鉛フタロシアニン顔料を含む、請求項6に記載の着色組成物。
- 前記緑色着色剤は、カラーインデックスピグメントグリーン7、カラーインデックスピグメントグリーン58およびカラーインデックスピグメントグリーン59から選ばれる少なくとも1種を含む、請求項6に記載の着色組成物。
- 前記着色組成物の全固形分中における前記着色剤の含有量が45質量%以上である、請求項1~9のいずれか1項に記載の着色組成物。
- 前記樹脂は、環状エーテル基を有する樹脂を含む、請求項1~10のいずれか1項に記載の着色組成物。
- 更に、重合性化合物と、光重合開始剤とを含む、請求項1~11のいずれか1項に記載の着色組成物。
- カラーフィルタ用である、請求項1~12のいずれか1項に記載の着色組成物。
- 請求項1~13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14に記載の膜を有する光学フィルタ。
- 請求項14に記載の膜を有する固体撮像素子。
- 請求項14に記載の膜を有する画像表示装置。
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CN115894777A (zh) * | 2022-11-18 | 2023-04-04 | 常州大学 | 一种丙烯酸改性共聚分散剂及其制备方法和应用 |
WO2023120036A1 (ja) * | 2021-12-22 | 2023-06-29 | 富士フイルム株式会社 | 樹脂組成物、膜、光学フィルタ、固体撮像素子および画像表示装置 |
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JP2015031857A (ja) * | 2013-08-05 | 2015-02-16 | 富士フイルム株式会社 | 着色感光性樹脂組成物、硬化膜、カラーフィルタ、カラーフィルタの製造方法、固体撮像素子、および画像表示装置 |
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2022
- 2022-03-03 WO PCT/JP2022/009249 patent/WO2022202204A1/ja active Application Filing
- 2022-03-03 JP JP2023508897A patent/JPWO2022202204A1/ja active Pending
- 2022-03-03 KR KR1020237027262A patent/KR20230130706A/ko unknown
- 2022-03-14 TW TW111109133A patent/TW202248364A/zh unknown
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JPH10260309A (ja) * | 1997-03-19 | 1998-09-29 | Jsr Corp | カラーフィルタ用感放射線性組成物 |
JPH1114825A (ja) * | 1997-04-28 | 1999-01-22 | Sumitomo Chem Co Ltd | カラーフィルター用緑色組成物およびカラーフィルター |
JP2010254842A (ja) * | 2009-04-27 | 2010-11-11 | Canon Inc | 色素化合物、該色素化合物を含有する顔料分散剤、顔料組成物、及び顔料分散体 |
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WO2023120036A1 (ja) * | 2021-12-22 | 2023-06-29 | 富士フイルム株式会社 | 樹脂組成物、膜、光学フィルタ、固体撮像素子および画像表示装置 |
CN115894777A (zh) * | 2022-11-18 | 2023-04-04 | 常州大学 | 一种丙烯酸改性共聚分散剂及其制备方法和应用 |
CN115894777B (zh) * | 2022-11-18 | 2023-09-26 | 常州大学 | 一种丙烯酸改性共聚分散剂及其制备方法和应用 |
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TW202248364A (zh) | 2022-12-16 |
KR20230130706A (ko) | 2023-09-12 |
JPWO2022202204A1 (ja) | 2022-09-29 |
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