WO2023167026A1 - Pigment de dicétopyrrolopyrrole, composition de pigment, composition colorée, filtre de couleur et capteur - Google Patents

Pigment de dicétopyrrolopyrrole, composition de pigment, composition colorée, filtre de couleur et capteur Download PDF

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WO2023167026A1
WO2023167026A1 PCT/JP2023/005890 JP2023005890W WO2023167026A1 WO 2023167026 A1 WO2023167026 A1 WO 2023167026A1 JP 2023005890 W JP2023005890 W JP 2023005890W WO 2023167026 A1 WO2023167026 A1 WO 2023167026A1
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pigment
coloring composition
meth
acrylate
group
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PCT/JP2023/005890
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English (en)
Japanese (ja)
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直也 立石
太郎 室星
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東洋インキＳｃホールディングス株式会社
東洋ビジュアルソリューションズ株式会社
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Publication of WO2023167026A1 publication Critical patent/WO2023167026A1/fr

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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
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/08—Naphthalimide dyes; Phthalimide 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/006—Preparation of organic pigments
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters

Definitions

  • the present invention relates to diketopyrrolopyrrole pigments, pigment compositions, coloring compositions, color filters and sensors.
  • image sensors such as C-MOS (Complementary Metal Oxide Semiconductor) and CCD (Charge Coupled Device) has grown significantly. ing. These image sensors generally perform color separation by arranging color filters each having filter segments of additive primary colors of B (blue), G (green), and R (red) on the light receiving elements. is.
  • Color filters for image sensors are required to have thinner films, improved color resolution, and improved color reproducibility. Needed.
  • the concentration of the coloring agent is increased, the coloring agent having a high coloring strength is used, and the like.
  • C.I. I. Pigment Red 254 has been used, but its tinting strength is not sufficient to meet the recent strong demand for thinner films.
  • C.I. I. Pigment Red 272 and the use of diketopyrrolopyrrole pigments such as described in Patent Document 3 have been studied, but there are problems such as poor stability of the dispersion when the concentration is increased and low transmittance at 600 nm or more. there were.
  • An object of the present invention is to provide a diketopyrrolopyrrole pigment, as a red colorant, which has both high tinting strength and high transmittance and has excellent dispersion stability.
  • Another object of the present invention is to provide a pigment composition, a coloring composition, a color filter, and a sensor using the pigment.
  • the present inventors have achieved both high tinting strength and high transmittance by using a specific diketopyrrolopyrrole pigment as a red colorant, and have excellent dispersion stability.
  • the present invention relates to a diketopyrrolopyrrole pigment characterized by being represented by the following general formula (1).
  • a 1 and A 2 each independently represent a five-membered or six-membered ring which may have a substituent, and the atoms forming the rings each independently A carbon atom, an oxygen atom, or a sulfur atom.
  • R 1 and R 2 each independently represent a hydrogen atom, an optionally substituted alkyl group having 1 to 10 carbon atoms, or a halogen atom.
  • the present invention also relates to a diketopyrrolopyrrole pigment characterized by being represented by the following general formula (2).
  • R 3 and R 4 each independently represent a hydrogen atom, an optionally substituted alkyl group having 1 to 10 carbon atoms, or a halogen atom;
  • R 5 and R 6 each independently It represents a hydrogen atom, an optionally substituted alkyl group having 1 to 10 carbon atoms, or an optionally substituted phenyl group.
  • the present invention also relates to a pigment composition characterized by containing the diketopyrrolopyrrole pigment and a dye derivative.
  • the present invention also relates to a coloring composition characterized by containing the diketopyrrolopyrrole pigment or the pigment composition and an organic solvent.
  • the present invention also relates to a coloring composition characterized by further containing a photopolymerizable monomer and/or a photopolymerizable initiator.
  • the present invention also relates to a color filter having a film formed from the coloring composition on a substrate.
  • the present invention also relates to a sensor having the color filter.
  • a diketopyrrolopyrrole pigment that achieves both high tinting strength and high transmittance and has excellent dispersion stability.
  • a pigment composition, a coloring composition, a color filter, and a sensor using the pigment can be provided.
  • the present invention is a diketopyrrolopyrrole pigment represented by the following general formula (1).
  • a 1 and A 2 each independently represent a five-membered or six-membered ring which may have a substituent, and the atoms forming the rings each independently A carbon atom, an oxygen atom, or a sulfur atom.
  • R 1 and R 2 each independently represent a hydrogen atom, an optionally substituted alkyl group having 1 to 10 carbon atoms, or a halogen atom.
  • R 7 to R 9 are five-membered or six-membered ring substituents, and are each an alkyl group having 1 to 10 carbon atoms, a trifluoromethyl group, a halogen atom, a nitro group, a cyano group, a carbamoyl group, a sulfamoyl group, or a carbon Examples include alkoxyl groups of numbers 1 to 4, but are not limited to these.
  • alkyl group of the alkyl group having 1 to 10 carbon atoms which may have a substituent may be linear or branched, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, n-hexyl group, heptyl group, octyl group, decyl group, 1,5-dimethylhexyl group, 1,6-dimethylheptyl group, 2-ethylhexyl group etc.
  • Alkyl group having a substituent includes, for example, trichloromethyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, 2,2-dibromoethyl group, 2,2,3,3-tetrafluoro propyl group, 2-ethoxyethyl group, 2-butoxyethyl group, 2-nitropropyl group, benzyl group, 4-methylbenzyl group, 4-tert-butylbenzyl group, 4-methoxybenzyl group and the like, but these include It is not limited.
  • phenyl group which may have a substituent examples include an alkyl group having 1 to 10 carbon atoms, a trifluoromethyl group, a halogen atom, a nitro group, a cyano group, a carbamoyl group, a sulfamoyl group, and an alkoxyl group having 1 to 4 carbon atoms. phenyl groups having substituents such as groups.
  • phenyl group p-methylphenyl group, 4-tert-butylphenyl group, p-nitrophenyl group, p-methoxyphenyl group, p-chlorophenyl group, 2,4-dichlorophenyl group, 3-carbamoyl
  • phenyl group p-methylphenyl group, 4-tert-butylphenyl group, p-nitrophenyl group, p-methoxyphenyl group, p-chlorophenyl group, 2,4-dichlorophenyl group, 3-carbamoyl Examples include, but are not limited to, a phenyl group and the like.
  • At least one of the atoms forming the five-membered ring or six-membered ring is preferably an oxygen atom or a sulfur atom, and the divalent compound represented by the following general formula (1a) Ketopyrrolopyrrole pigments are more preferred.
  • a 1 and a 2 each independently represent a five-membered or six-membered ring which may have a substituent, and the atoms forming the ring each independently A carbon atom, an oxygen atom, or a sulfur atom.
  • Y 1 and Y 2 each independently represent an oxygen atom or a sulfur atom.
  • R 1 and R 2 each independently represent a hydrogen atom, an optionally substituted alkyl group having 1 to 10 carbon atoms, or a halogen atom.
  • the diketopyrrolopyrrole pigment in the present invention preferably has general formula (2) from the viewpoint of coloring power and transmittance.
  • R 3 and R 4 each independently represent a hydrogen atom, an optionally substituted alkyl group having 1 to 10 carbon atoms, or a halogen atom;
  • R 5 and R 6 each independently It represents a hydrogen atom, an optionally substituted alkyl group having 1 to 10 carbon atoms, or an optionally substituted phenyl group.
  • at least one of X 1 to X 6 is preferably an oxygen atom or a sulfur atom
  • X 3 and X 6 are an oxygen atom or a sulfur atom. is more preferable.
  • diketopyrrolopyrrole pigment of the present invention are listed below, but are not limited to these.
  • diketopyrrolopyrrole pigments (1-1 to 21) are preferred, and (1-6 to 21) are preferred, and (1-6 , 9-16, 19-21) are particularly preferred.
  • the method for producing the diketopyrrolopyrrole pigment of the present invention is not particularly limited, it can be produced most conveniently by a succinic acid diester synthesis method. That is, 2 mol of a benzonitrile compound represented by the following general formula (4) is added to 1 mol of a succinic acid diester in an inert organic solvent such as tert-amyl alcohol in the presence of an alkali metal or an alkali metal alkoxide. , a condensation reaction is performed at a high temperature of 80 to 110° C. to produce an alkali metal salt of the diketopyrrolopyrrole compound, and then water, alcohol, acid, etc.
  • a succinic acid diester synthesis method That is, 2 mol of a benzonitrile compound represented by the following general formula (4) is added to 1 mol of a succinic acid diester in an inert organic solvent such as tert-amyl alcohol in the presence of an alkali metal or an alkali metal
  • diketopyrrolopyrrole compound Various diketopyrrolopyrrole pigments can be obtained by protonating with At this time, the primary particle size obtained can be controlled by the temperature in protonation, the type, ratio and amount of water, alcohol or acid.
  • a 3 represents a five-membered or six-membered ring which may have a substituent, and the atoms forming the ring are each independently a carbon atom, an oxygen atom or a sulfur atom is.
  • R 10 represents a hydrogen atom, an optionally substituted alkyl group having 1 to 10 carbon atoms, or a halogen atom.
  • the pigment composition of the present invention contains the diketopyrrolopyrrole pigment and dye derivative of the present invention.
  • a dye derivative is a compound having an acidic group, a basic group, a neutral group, or the like in an organic dye residue.
  • Dye derivatives include, for example, compounds having acidic substituents such as sulfo, carboxy, or phosphate groups, and amine salts thereof, sulfonamide groups, or terminally basic substituents such as tertiary amino groups. compounds, and compounds having neutral substituents such as phenyl groups and phthalimidoalkyl groups.
  • Organic dyes include, for example, diketopyrrolopyrrole pigments, anthraquinone pigments, quinacridone pigments, dioxazine pigments, perinone pigments, perylene pigments, thiazineindigo pigments, triazine pigments, benzimidazolone pigments, benzoiso Indole pigments such as indole, isoindoline pigments, isoindolinone pigments, quinophthalone pigments, naphthol pigments, threne pigments, metal complex pigments, azo pigments such as azo, disazo and polyazo.
  • diketopyrrolopyrrole pigments such as indole, isoindoline pigments, isoindolinone pigments, quinophthalone pigments, naphthol pigments, threne pigments, metal complex pigments, azo pigments such as azo, disazo and polyazo.
  • diketopyrrolopyrrole-based dye derivatives JP 2001-220520, WO2009/081930, WO2011/052617, WO2012/102399, JP 2017-156397, phthalocyanine Dye derivatives, JP-A-2007-226161, WO2016/163351 pamphlet, JP-A-2017-165820, Japanese Patent No.
  • dye derivative contained in the pigment composition of the present invention those derived from diketopyrrolopyrrole-based pigments, anthraquinone-based pigments, quinophthalone-based pigments, and azo-based pigments as organic dye residues have coloring power, refining efficiency, and dispersion. It is preferable from the viewpoint of stability.
  • the pigment derivative contained in the pigment composition of the present invention is preferably added in an amount of 0 to 30 parts by mass, more preferably 1 to 20 parts by mass, per 100 parts by mass of the diketopyrrolopyrrole pigment.
  • the pigment composition of the present invention may be prepared by simply mixing a diketopyrrolopyrrole pigment powder and a pigment derivative powder, but may be prepared by mixing a dissolver, high speed mixer, homomixer, kneader, roll mill, attritor, sand mill, A method of mechanically mixing pigment powder and pigment derivative powder using various grinders, a method of adding a solution containing a pigment derivative to a water or organic solvent suspension system of the pigment, and depositing the pigment derivative on the surface of the pigment.
  • the pigment composition may be obtained by co-dissolving the organic pigment and the dye derivative in a solvent having a strong dissolving power such as sulfuric acid, followed by co-precipitation with a poor solvent such as water.
  • the diketopyrrolopyrrole pigment used in the pigment composition of the present invention is preferably finely divided.
  • the method of refining is not particularly limited, and for example, any of wet grinding, dry grinding, and dissolution precipitation method can be used. etc., and can be miniaturized.
  • the salt milling process is performed by subjecting a mixture of a pigment, a water-soluble inorganic salt, and a water-soluble organic solvent to a kneader, two-roll mill, three-roll mill, ball mill, attritor, sand mill, planetary mixer, or the like in batch or continuous mode.
  • the mixture is mechanically kneaded while being heated using a kneader, and then washed with water to remove the water-soluble inorganic salt and the water-soluble organic solvent.
  • the water-soluble inorganic salt functions as a crushing aid, and the high hardness of the inorganic salt is used to crush the pigment during salt milling.
  • water-soluble inorganic salt sodium chloride, potassium chloride, sodium sulfate, etc. can be used, but it is preferable to use sodium chloride (salt) from the viewpoint of price.
  • the water-soluble inorganic salt is preferably used in an amount of 50 to 2,000 parts by mass, most preferably 300 to 1,000 parts by mass, based on 100 parts by mass of the pigment, from the viewpoint of both processing efficiency and production efficiency.
  • the water-soluble organic solvent has the function of moistening the pigment and the water-soluble inorganic salt, and is not particularly limited as long as it dissolves (mixes) in water and does not substantially dissolve the inorganic salt used.
  • a high boiling point solvent having a boiling point of 120° C. or higher is preferable from the viewpoint of safety.
  • the water-soluble organic solvent is preferably used in an amount of 5 to 1,000 parts by mass, most preferably 50 to 500 parts by mass, per 100 parts by mass of the pigment.
  • a pigment derivative may be added, which is very effective in refining and regulating pigments.
  • the amount of the pigment derivative to be used is preferably in the range of not affecting the color tone, that is, in the range of 0.5 to 40% by weight with respect to 100% by weight of the pigment.
  • resin may be added as necessary during the salt milling process.
  • the type of resin used is not particularly limited, and natural resins, modified natural resins, synthetic resins, synthetic resins modified with natural resins, and the like can be used.
  • the resins used are preferably solid at room temperature, water-insoluble, and more preferably partially soluble in the above organic solvents.
  • the amount of the resin used is preferably in the range of 5 to 200 parts by weight per 100 parts by weight of the pigment.
  • the diketopyrrolopyrrole pigment By subjecting the diketopyrrolopyrrole pigment to a salt milling process, it can be made more uniformly fine, and the coloring power, transmittance, and stability of the dispersion can be improved in a well-balanced manner.
  • the average primary particle size of the diketopyrrolopyrrole pigment of the present invention is preferably in the range of 30 to 200 nm. If the average primary particle size is 200 nm or more, the coloring power is high, but the transmittance is low. If the average primary particle size is less than 30 nm, the transmittance is improved, but the resistance is lowered. In addition, when the specific surface area of the coloring agent increases, the cohesive force increases, and the dispersibility and storage stability of the coloring composition deteriorate.
  • the average primary particle size was measured using a transmission electron microscope (TEM) H-7650 manufactured by Hitachi High-Technologies Co., Ltd. by directly measuring the size of the primary particles from an electron micrograph. Specifically, the minor axis diameter and the major axis diameter of the primary particles of each pigment were measured, and the average was used as the particle diameter of the primary pigment particles. Next, for 100 or more pigment particles, the volume (weight) of each particle was obtained by approximating a cube with the obtained particle size, and the volume average particle size was taken as the average primary particle size.
  • TEM transmission electron microscope
  • the diketopyrrolopyrrole pigment or pigment composition of the present invention can be used as a coloring composition by using it in combination with an organic solvent.
  • a binder resin, a resin-type dispersant, and other colorants may be included as necessary.
  • the pigment derivative is adsorbed on the surface of the pigment, and the surface of the pigment becomes polar, and the resin-type dispersant is adsorbed.
  • the compatibility with pigments, dye derivatives, resin type dispersants, organic solvents, and other additives is improved, and the dispersion stability and viscosity stability over time of the colored composition are improved.
  • the coating film has excellent stability over time when the coloring composition is applied to a glass substrate or the like, and the waiting time (PCD: Post Coating Delay) from the application of the coloring composition to exposure and the exposure
  • PCD Post Coating Delay
  • PED Post Exposure Delay
  • the surface of the pigment is adsorbed and coated with the pigment derivative and the resin-type dispersant, it is possible to suppress the precipitation of crystals due to aggregation and sublimation of the pigment when the coating film is heated and baked. Further, variation in development time and development residue are suppressed.
  • the binder resin is a resin having a transmittance of 80% or more in the entire wavelength range of 400-700 nm. Note that the transmittance is preferably 95% or more.
  • binder resins include, for example, thermoplastic resins, thermosetting resins, active energy ray-curable resins, and the like.
  • the active energy ray-curable resin may have an active energy ray-reactive functional group in a thermoplastic resin or a thermosetting resin.
  • binder resins include alkali-soluble resins and the like. Alkali-solubility is for imparting development solubility in the alkali development step during production of a color filter, which will be described later, and requires an acidic group.
  • the binder resin can be used alone or in combination of two or more.
  • binder resin that can be used in the coloring composition of the present invention will be described in detail.
  • Thermoplastic resins include, for example, acrylic resin, butyral resin, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, polyurethane resin, polyester resin, vinyl resin, alkyd Resins, polystyrene resins, polyamide resins, rubber resins, cyclized rubber resins, celluloses, polyethylene (HDPE, LDPE), polybutadiene, polyimide resins, and the like.
  • Alkali-soluble thermoplastic resins include, for example, resins having acidic groups such as carboxyl groups and sulfone groups.
  • Alkali-soluble thermoplastic resins include, for example, acrylic resins having acidic groups, styrene/styrenesulfonic acid copolymers, ethylene/(meth)acrylic acid copolymers, and the like.
  • acrylic resins having an acidic group and a styrene/styrenesulfonic acid copolymer are preferred from the standpoint of improving developability, heat resistance and transparency.
  • the active energy ray-curable alkali-soluble resin preferably has an ethylenically unsaturated double bond. Ethylenically unsaturated double bonds can be introduced, for example, by methods (i) and (ii) shown below.
  • the resin is three-dimensionally crosslinked by the effect of the active energy ray, thereby increasing the crosslink density and improving chemical resistance.
  • Method (i) is, for example, a copolymer obtained by copolymerizing an ethylenically unsaturated monomer having an epoxy group with another monomer, and adding an ethylenically unsaturated divalent A carboxyl group of unsaturated monobasic acid having a double bond is subjected to an addition reaction. Then, the produced hydroxyl group is reacted with a polybasic acid anhydride to introduce an ethylenically unsaturated double bond and a carboxyl group.
  • Ethylenically unsaturated monomers having an epoxy group include, for example, glycidyl (meth)acrylate, methylglycidyl (meth)acrylate, 2-glycidoxyethyl (meth)acrylate, 3,4-epoxybutyl (meth)acrylate, and 3,4-epoxycyclohexyl (meth)acrylate.
  • glycidyl (meth)acrylate is preferred from the viewpoint of reactivity with unsaturated monobasic acid.
  • Unsaturated monobasic acids include (meth)acrylic acid, crotonic acid, o-, m-, p-vinylbenzoic acid, and ⁇ -position haloalkyl, alkoxyl, halogen, nitro, and cyano substituted products of (meth)acrylic acid.
  • Carboxylic acid etc. are mentioned.
  • Polybasic acid anhydrides include tetrahydrophthalic anhydride, phthalic anhydride, hexahydrophthalic anhydride, succinic anhydride, and maleic anhydride. If necessary, such as increasing the number of carboxyl groups, using a tricarboxylic anhydride such as trimellitic anhydride or using a tetracarboxylic dianhydride such as pyromellitic dianhydride, the remaining It is also possible to hydrolyze the anhydride group.
  • monomers include the following. For example, methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, cyclohexyl (meth)acrylate, stearyl (meth)acrylate, lauryl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, isobornyl (meth)acrylate, phenyl (meth)acrylate, benzyl (meth)acrylate (meth)acrylates such as acrylate, phenoxyethyl (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, methoxypolypropylene glycol (meth)acrylate, or
  • an ethylenically unsaturated monomer having a carboxyl group and a part of the side chain carboxyl group of a copolymer obtained by copolymerizing another monomer 2 is a method of subjecting an ethylenically unsaturated monomer having an epoxy group to an addition reaction to introduce an ethylenically unsaturated double bond and a carboxyl group.
  • Method (ii) is obtained by copolymerizing an ethylenically unsaturated monomer having a hydroxyl group with another monomer, and adding an ethylenically unsaturated monomer having an isocyanate group to the side chain hydroxyl group of the copolymer. This is a method of reacting the isocyanate group of the monomer.
  • Ethylenically unsaturated monomers having a hydroxyl group are, for example, 2-hydroxyethyl (meth)acrylate, 2- or 3-hydroxypropyl (meth)acrylate, 2- or 3- or 4-hydroxybutyl (meth)acrylate, Hydroxyalkyl methacrylates such as glycerol mono(meth)acrylate or cyclohexanedimethanol mono(meth)acrylate can be mentioned.
  • polyether mono(meth)acrylate obtained by addition polymerization of ethylene oxide, propylene oxide, and/or butylene oxide to hydroxyalkyl (meth)acrylate, poly ⁇ -valerolactone, poly ⁇ -caprolactone, and/or poly Polyester mono(meth)acrylates to which 12-hydroxystearic acid or the like is added are also included.
  • 2-Hydroxyethyl methacrylate or glycerol mono(meth)acrylate is preferred from the viewpoint of suppressing foreign matter on the coating film, and from the viewpoint of sensitivity, it is preferable to use one having 2 to 6 hydroxyl groups. is preferred, and glycerol mono(meth)acrylate is more preferred.
  • Examples of ethylenically unsaturated monomers having an isocyanate group include 2-(meth)acryloylethyl isocyanate, 2-(meth)acryloyloxyethyl isocyanate, 1,1-bis[methacryloyloxy]ethyl isocyanate, and the like. be done.
  • alkali-soluble resin examples include, in addition to the other ethylenically unsaturated monomers already described, N-substituted maleimides, alkyleneoxy group-containing monomers, and phosphate ester group-containing ethylenically unsaturated monomers. monomers, carboxyl group-containing ethylenically unsaturated monomers, and the like.
  • N-substituted maleimides include, for example, cyclohexylmaleimide, phenylmaleimide, methylmaleimide, ethylmaleimide, 1,2-bismaleimidoethane, 1,6-bismaleimidohexane, 3-maleimidopropionic acid, 6,7-methylenedioxy- 4-methyl-3-maleimidocoumarin, 4,4′-bismaleimidodiphenylmethane, bis(3-ethyl-5-methyl-4-maleimidophenyl)methane, N,N′-1,3-phenylenedimaleimide, N, N'-1,4-phenylenedimaleimide, N-(1-pyrenyl)maleimide, N-(2,4,6-trichlorophenyl)maleimide, N-(4-aminophenyl)maleimide, N-(4-nitro phenyl)maleimide, N-benzylmaleimide, N-brom
  • alkyleneoxy group-containing monomers examples include EO-modified cresol acrylate, n-nonylphenoxy polyethylene glycol acrylate, phenoxyethyl acrylate, ethoxylated phenyl acrylate, ethylene oxide (EO)-modified (meth)acrylate of phenol, and paracumylphenol.
  • examples include EO- or propylene oxide (PO)-modified (meth)acrylates, nonylphenol EO-modified (meth)acrylates, nonylphenol PO-modified (meth)acrylates, and the like.
  • the carboxyl group-containing ethylenically unsaturated monomer the monomers already described can be used.
  • the phosphate ester group-containing ethylenically unsaturated monomer is, for example, a compound obtained by reacting the hydroxyl group of the hydroxyl group-containing ethylenically unsaturated monomer with a phosphorylating agent such as phosphorus pentoxide or polyphosphoric acid. be.
  • the coloring composition herein can contain an alkali-soluble resin having no ethylenically unsaturated double bonds in order to adjust the degree of cure of the coating.
  • the weight average molecular weight (Mw) of the alkali-soluble resin in the present invention is 2,000 or more and 40,000 or less, preferably 3,000 or more and 30,000 or less, and 4,000, in order to impart alkali developing solubility. More than 20,000 or less is more preferable. Also, the value of Mw/Mn is preferably 10 or less. If the weight-average molecular weight (Mw) is less than 2,000, the adhesiveness to the substrate is lowered and the exposure pattern is less likely to remain. If it exceeds 40,000, the solubility in alkali development will be lowered, and a residue will be generated to deteriorate the linearity of the pattern.
  • the acid value of the alkali-soluble resin in the present invention is from 50 to 200 (KOHmg/g) in order to impart solubility in alkali development, preferably from 70 to 180, more preferably from 90 to 170. is. If the acid value is less than 50, the solubility in alkali development is lowered, and residues are generated, resulting in poor pattern linearity. If it exceeds 200, the adhesion to the substrate will be lowered, and the exposure pattern will be difficult to remain.
  • Each raw material used to synthesize the binder resin can be used alone or in combination of two or more.
  • thermosetting compound in the present invention, a thermosetting compound can be used in combination with the thermoplastic resin as the binder resin.
  • a thermosetting compound reacts during baking of the filter segment and increases the crosslink density of the coating film, so that the heat resistance of the filter segment is improved. Pigment agglomeration during baking of the filter segment is suppressed, and the effect of improving the contrast ratio can be obtained.
  • thermosetting compound may be a low-molecular-weight compound or a high-molecular-weight compound such as a resin.
  • thermosetting compounds include epoxy compounds, oxetane compounds, benzoguanamine compounds, melamine compounds, urea compounds, and phenolic compounds, but the present invention is not limited thereto. Epoxy compounds and oxetane compounds are preferably used in the coloring composition of the present invention.
  • the content of the binder resin used when producing the colored composition is preferably 20 to 400 parts by mass, more preferably 50 to 250 parts by mass, with respect to 100 parts by mass of the coloring agent. When contained in an appropriate amount, a film can be easily formed, and good color characteristics can be easily obtained.
  • the coloring composition of the present invention can contain a resin type dispersant.
  • the dispersant has a colorant-affinity site that has the property of adsorbing to the added colorant and a site that is compatible with the colorant carrier, and adsorbs to the added colorant to stabilize dispersion on the colorant carrier. It works to transform.
  • resin-type dispersants include polyurethanes, polycarboxylic acid esters such as polyacrylates, unsaturated polyamides, polycarboxylic acids, polycarboxylic acid (partial) amine salts, polycarboxylic acid ammonium salts, and polycarboxylic acid alkylamine salts.
  • Oily dispersants such as (meth)acrylic acid-styrene copolymer, (meth)acrylic acid-(meth)acrylic acid ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol, water-soluble such as polyvinylpyrrolidone Resins, water-soluble polymer compounds, polyesters, modified polyacrylates, ethylene oxide/propylene oxide addition compounds, phosphoric acid esters, etc. are used, and these can be used alone or in combination of two or more. It is not necessarily limited to these.
  • a resin-type dispersant When a resin-type dispersant is used in combination in the present invention, one having an acidic substituent is preferred, and among these, one having an aromatic carboxyl group is particularly preferred because it has a particularly large effect of preventing reaggregation of the colorant after dispersion.
  • a resin-type dispersant having an aromatic carboxyl group WO2008/007776, JP-A-2008-029901, JP-A-2009-155406, JP-A-2009-155406, JP-A-2010-185934 , but not limited to those described in JP-A-2011-157416.
  • the resin-type dispersant is preferably used in an amount of about 5 to 200 parts by mass with respect to the total amount of the coloring agent, and more preferably in an amount of about 5 to 100 parts by mass from the viewpoint of film-forming properties.
  • the colored composition of the present invention can contain other colorants as necessary within a range that does not impair the effects of the present invention.
  • Other colorants may be pigments or dyes, and may be used alone or in combination of two or more. Specific examples of other colorants are shown below, but are not limited thereto.
  • red pigment for example, C.I. I. Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 37, 38, 41, 47, 48, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 50:1, 52:1, 52:2, 53, 53:1, 53:2, 53: 3, 57, 57:1, 57:2, 58:4, 60, 63, 63:1, 63:2, 64, 64:1, 68, 69, 81, 81:1, 81:2, 81: 3, 81:4, 83, 88, 90:1, 101, 101:1, 104, 108, 108:1, 109, 112, 113, 114, 122, 123, 144, 146, 147, 149, 151, 166, 168, 169, 170, 172, 173, 174, 175, 176, 177, 178, 179, 181, 184, 185, 187, 188, 190, 193,
  • C.I. I. Pigment Red 48 1, 122, 177, 224, 242, 254, 269, 272, 291, 295, 296, the pigment described in JP-A-2014-134712, the pigment described in Japanese Patent No. 6368844 Yes, more preferably C.I. I. Pigment Red 177, 254, 269, 272, 291, 295, 296, pigments described in JP-A-2014-134712, and pigments described in Japanese Patent No. 6368844.
  • red dyes examples include xanthene-based, azo-based (pyridone-based, barbituric acid-based, metal complex-based, etc.), disazo-based, and anthraquinone-based dyes. Specifically, C.I. I. Acid Red 52, 87, 92, 289, 338 and the like salt-forming compounds of xanthene acid dyes.
  • C.I. I. Pigment Orange 71 and 73 Preferably C.I. I. Pigment Orange 71 and 73.
  • orange dyes and/or yellow dyes examples include quinoline-based, azo-based (pyridone-based, barbituric acid-based, metal complex-based, etc.), disazo-based, and methine-based dyes.
  • C.I. I. Pigment Violet 1 1:1, 2, 2:2, 3, 3:1, 3:3, 5, 5:1, 14, 15, 16, 19, 23, 25, 27, 29, 31, 32, 37, 39, 42, 44, 47, 49, 50 and the like.
  • C.I. I. Pigment Violet 19 or 23 more preferably C.I. I. Pigment Violet 23.
  • the coloring composition of the present invention contains an organic solvent. This facilitates adjustment of the viscosity of the composition.
  • Organic solvents include, for example, ethyl lactate, butyl lactate, benzyl alcohol, 1,2,3-trichloropropane, 1,3-butanediol, 1,3-butylene glycol, 1,3-butylene glycol diacetate, 1, 4-dioxane, 2-heptanone, 2-methyl-1,3-propanediol, 3,5,5-trimethyl-2-cyclohexen-1-one, 3,3,5-trimethylcyclohexanone, ethyl 3-ethoxypropionate , 3-methyl-1,3-butanediol, 3-methoxy-3-methyl-1-butanol, 3-methoxy-3-methylbutyl acetate, 3-methoxybutanol, 3-methoxybutyl acetate, 4-heptanone, m -xylene, m-diethylbenzene, m-dichlorobenzene, N,N-dimethylacetamide,
  • organic solvents in the case of coating applications, it is preferable to include an organic solvent having a boiling point of 120°C or higher and 180°C or lower at 1 atm from the viewpoint of coating properties and drying properties.
  • organic solvent having a boiling point of 120°C or higher and 180°C or lower at 1 atm from the viewpoint of coating properties and drying properties.
  • the coloring composition of the present invention can further contain a photopolymerizable monomer and/or a photopolymerizable initiator. Thereby, it can be used as a photosensitive coloring composition.
  • the photopolymerizable monomers contained in the coloring composition of the present invention include monomers or oligomers that are cured by ultraviolet light to form transparent resins.
  • Photopolymerizable monomers include, for example, methyl (meth)acrylate, ethyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, cyclohexyl (meth)acrylate, ⁇ -carboxyethyl (Meth)acrylate, polyethylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, triethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate , phenoxytetraethylene glycol (meth)acrylate, phenoxyhexaethyleneglycol (meth)acrylate, trimethylolpropane PO-modified tri(meth)acrylate, trimethylolpropane EO-modified tri(meth)acrylate, isocyanuric acid EO-modified di(meth)acrylate
  • the photopolymerizable monomers can contain photopolymerizable monomers having acid groups.
  • acid groups include sulfonic acid groups, carboxyl groups, and phosphoric acid groups.
  • Photopolymerizable monomers having an acid group include, for example, polyhydric alcohols and (meth)acrylic acid esters of free hydroxyl group-containing poly(meth)acrylates and dicarboxylic acids; Examples thereof include esterified products with hydroxyalkyl (meth)acrylates. Specific examples include monohydroxyoligoacrylates or monohydroxyoligomethacrylates such as trimethylolpropane diacrylate, trimethylolpropane dimethacrylate, pentaerythritol triacrylate, pentaerythritol trimethacrylate, dipentaerythritol pentaacrylate, and dipentaerythritol pentamethacrylate.
  • monohydroxyoligoacrylates or monohydroxyoligomethacrylates such as trimethylolpropane diacrylate, trimethylolpropane dimethacrylate, pentaerythritol triacrylate, pentaerythritol trimethacrylate, dipenta
  • the photopolymerizable monomer can contain a monomer having an ethylenically unsaturated bond and a urethane bond.
  • the monomer is, for example, a polyfunctional urethane acrylate obtained by reacting a polyfunctional isocyanate with a (meth)acrylate having a hydroxyl group, or reacting a polyfunctional isocyanate with an alcohol and further reacting a (meth)acrylate having a hydroxyl group. and polyfunctional urethane acrylates obtained by
  • (Meth)acrylates having a hydroxyl group include 2-hydroxyethyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, trimethylolpropane di(meth)acrylate, pentaerythritol tri(meth)acrylate, ditrimethylolpropane tri(meth)acrylate, ) acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol ethylene oxide-modified penta(meth)acrylate, dipentaerythritol propylene oxide-modified penta(meth)acrylate, dipentaerythritol caprolactone-modified penta(meth)acrylate, glycerol acrylate methacrylate , glycerol dimethacrylate, 2-hydroxy-3-acryloylpropyl methacrylate, a reaction product of an epoxy group-containing compound and carboxy(meth)acrylate, hydroxyl
  • polyfunctional isocyanates include tolylene diisocyanate, hexamethylene diisocyanate, diphenylmethylene diisocyanate, isophorone diisocyanate, polyisocyanate, and the like.
  • the photopolymerizable monomers can be used alone or in combination of two or more.
  • the blending amount of the photopolymerizable monomer is preferably 1 to 50% by mass, more preferably 2 to 40% by mass, based on 100% by mass of the non-volatile matter of the coloring composition. Curability and developability are further improved when blended in an appropriate amount.
  • Photopolymerization initiators are, for example, 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexylphenyl ketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-(dimethylamino)-1-[4-(4-morpholino)phenyl ]-2-(phenylmethyl)-1-butanone, or 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone, etc.
  • acetophenone compounds benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, or benzyl dimethyl ketal; benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated Benzophenone compounds such as benzophenone, 4-benzoyl-4'-methyldiphenylsulfide, or 3,3',4,4'-tetra(t-butylperoxycarbonyl)benzophenone; thioxanthone, 2-chlorothioxanthone, 2-methyl Thioxanthone compounds such as thioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone, or 2,4-diethylthioxanthone; 2,4,6-trichloro-s-triazine, 2-phen
  • the photopolymerization initiator can be used alone or in combination of two or more.
  • oxime ester compound In oxime ester-based compounds, the absorption of ultraviolet light causes cleavage of the NO bond of the oxime to produce iminyl radicals and alkyloxy radicals. Since these radicals are further decomposed to generate highly active radicals, a pattern can be formed with a small amount of exposure.
  • the colorant concentration of the coloring composition is high, the ultraviolet transmittance of the coating film may be low and the degree of curing of the coating film may be low.
  • Oxime ester compounds are oximes described in JP-A-2007-210991, JP-A-2009-179619, JP-A-2010-037223, JP-A-2010-215575, JP-A-2011-020998, etc. Ester-based photopolymerization initiators can be mentioned.
  • the content of the photopolymerization initiator is preferably 2 to 50 parts by mass, more preferably 2 to 30 parts by mass, based on 100 parts by mass of the colorant. When blended in an appropriate amount, the photocurability and developability are further improved.
  • the coloring composition of the present invention can contain a sensitizer.
  • Sensitizers include chalcone derivatives, unsaturated ketones such as dibenzalacetone, 1,2-diketone derivatives such as benzyl and camphorquinone, benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, and anthraquinone derivatives.
  • xanthene derivatives thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, polymethine dyes such as oxonol derivatives, acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indoline derivatives, Azulene derivatives, azulenium derivatives, squarylium derivatives, porphyrin derivatives, tetraphenylporphyrin derivatives, triarylmethane derivatives, tetrabenzoporphyrin derivatives, tetrapyrazinoporphyrazine derivatives, phthalocyanine derivatives, tetraazaporphyrazine derivatives, tetraquinoxalyloporphyrazine derivatives , naphthalocyanine derivatives, subphthalo
  • sensitizers that are particularly suitable for sensitization. More specifically, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 2,4-dichlorothioxanthone, 2-isopropylthioxanthone, 4-isopropylthioxanthone, 1-chloro-4-propoxythioxanthone, 4,4′-bis (Dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(ethylmethylamino)benzophenone, N-ethylcarbazole, 3-benzoyl-N-ethylcarbazole, 3,6-dibenzoyl- N-ethylcarbazole or the like is used.
  • the sensitizer can be used alone or in combination of two or more.
  • the content of the sensitizer is preferably 3 to 60 parts by mass, more preferably 5 to 50 parts by mass, relative to 100 parts by mass of the photopolymerization initiator. When contained in an appropriate amount, curability and developability are further improved.
  • the coloring composition of the present invention preferably contains a thiol chain transfer agent as a chain transfer agent.
  • a thiol chain transfer agent By using a thiol together with a photopolymerization initiator, in the radical polymerization process after light irradiation, it acts as a chain transfer agent and generates thiyl radicals that are less susceptible to polymerization inhibition by oxygen, so the resulting colored composition has high sensitivity. Become.
  • polyfunctional aliphatic thiols bonded to aliphatic groups such as methylene and ethylene groups having two or more thiol groups are preferred. More preferred are polyfunctional aliphatic thiols having 4 or more thiol groups.
  • Polyfunctional thiols include, for example, hexanedithiol, decanedithiol, 1,4-butanediol bisthiopropionate, 1,4-butanediol bisthioglycolate, ethylene glycol bisthioglycolate, ethylene glycol bisthiopropio trimethylolpropane tristhioglycolate, trimethylolpropane tristhiopropionate, trimethylolpropane tris(3-mercaptobutyrate), pentaerythritol tetrakisthioglycolate, pentaerythritol tetrakisthiopropionate, trimercaptopropionic acid tris(2-hydroxyethyl)isocyanurate, 1,4-dimethylmercaptobenzene, 2,4,6-trimercapto-s-triazine, 2-(N,N-dibutylamino)-4,6-dimer
  • the thiol-based chain transfer agent can be used alone or in combination of two or more.
  • the content of the thiol-based chain transfer agent is preferably 0.1 to 10% by mass, more preferably 0.1 to 3% by mass, based on 100% by mass of the non-volatile matter of the coloring composition.
  • the photosensitivity and tapered shape are improved, and wrinkles are less likely to occur on the coating surface.
  • the coloring composition of the present invention can contain a polymerization inhibitor. This makes it possible to suppress exposure due to diffracted light from the mask during photolithographic exposure, making it easier to obtain a pattern of a desired shape.
  • polymerization inhibitors examples include catechol, resorcinol, 1,4-hydroquinone, 2-methylcatechol, 3-methylcatechol, 4-methylcatechol, 2-ethylcatechol, 3-ethylcatechol, 4-ethylcatechol, 2- Propylcatechol, 3-propylcatechol, 4-propylcatechol, 2-n-butylcatechol, 3-n-butylcatechol, 4-n-butylcatechol, 2-tert-butylcatechol, 3-tert-butylcatechol, 4- Alkylcatechol compounds such as tert-butylcatechol and 3,5-di-tert-butylcatechol, 2-methylresorcinol, 4-methylresorcinol, 2-ethylresorcinol, 4-ethylresorcinol, 2-propylresorcinol, 4-propyl Alkylresorcinol compounds such as resorcinol, 2-n-butylresorcinol, 4-n-butyl
  • the content of the polymerization inhibitor is preferably 0.01 to 0.4% by mass based on 100% by mass of the non-volatile content of the coloring composition. Within this range, the effect of the polymerization inhibitor is increased, and the straightness of the taper, the wrinkles of the coating film, the pattern resolution, etc. are improved.
  • the coloring composition of the present invention may contain an ultraviolet absorber.
  • the ultraviolet absorber in the present invention is an organic compound having an ultraviolet absorption function, and includes benzotriazole-based compounds, triazine-based compounds, benzophenone-based compounds, salicylic acid ester-based compounds, cyanoacrylate-based compounds, and salicylate-based compounds. .
  • the content of the ultraviolet absorber is preferably 5 to 70% by mass based on the total 100% by mass of the photopolymerization initiator and the ultraviolet absorber. When contained in an appropriate amount, the resolution after development is further improved.
  • the total content of the photopolymerization initiator and the ultraviolet absorber is preferably 1 to 20% by mass based on 100% by mass of the non-volatile content of the coloring composition.
  • the adhesion between the substrate and the film is further improved, and good resolution can be obtained.
  • Benzotriazole compounds include 2-(5-methyl-2-hydroxyphenyl)benzotriazole, 2-(2-hydroxy-5-t-butylphenyl)-2H-benzotriazole, 2-[2-hydroxy-3,5 -bis( ⁇ , ⁇ -dimethylbenzyl)phenyl]-2H-benzotriazole, 2-(3-tbutyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole, 2-(2'-hydroxy- 5′-t-octylphenyl)benzotriazole, 5% 2-methoxy-1-methylethyl acetate and 95% benzenepropanoic acid, 3-(2H-benzotriazol-2-yl)-(1,1-dimethyl ethyl)-4-hydroxy, a mixture of C7-9 side chain and linear alkyl esters, 2-(2H-benzotriazol-2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol,
  • Triazine compounds include 2,4-bis(2,4-dimethylphenyl)-6-(2-hydroxy-4-n-octyloxyphenyl)-1,3,5-triazine, 2-[4,6 -bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-[3-(dodecyloxy)-2-hydroxypropoxy]phenol, 2-(2,4-dihydroxyphenyl )-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine and (2-ethylhexyl)-glycidate ester reaction product, 2,4-bis "2-hydroxy-4- butoxyphenyl"-6-(2,4-dibutoxyphenyl)-1,3,5-triazine, 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-(hexyl oxy)phenol, 2-(4,6-diphenyl-1,3,5-triazin-2
  • Benzophenone compounds include 2,4-di-hydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-n-octoxybenzophenone, 2,2′-di-hydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 4-dodecyloxy-2-hydroxybenzophenone, 2-hydroxy-4-octadecyloxybenzophenone, 2,2'dihydroxy-4,4'-dimethoxybenzophenone, 2 , 2′,4,4′-tetrahydroxybenzophenone, 2-hydroxy-4-methoxy-2′-carboxybenzophenone and the like.
  • oligomer type and polymer type compounds having a benzophenone structure can also be used.
  • salicylate compounds include phenyl salicylate, p-octylphenyl salicylate, and p-tertbutylphenyl salicylate.
  • oligomer type and polymer type compounds having a salicylic acid ester structure can also be used.
  • the coloring composition of the present invention can contain an antioxidant.
  • Antioxidants prevent the photopolymerization initiators and thermosetting compounds contained in the coloring composition from oxidizing and yellowing due to the heat process during thermal curing and ITO annealing, and improve the transmittance of the coating film. can.
  • the colorant concentration of the coloring composition is high, the amount of the coating film cross-linking component is reduced, so measures such as using a highly sensitive cross-linking component and increasing the amount of the photopolymerization initiator are taken, resulting in strong yellowing in the thermal process. phenomena can be seen. Therefore, by including an antioxidant, it is possible to prevent yellowing due to oxidation during the heating process and to obtain a high transmittance of the coating film.
  • Antioxidants include, for example, hindered phenol-based, hindered amine-based, phosphorus-based, sulfur-based, and hydroxylamine-based compounds.
  • the antioxidant is preferably a compound containing no halogen atom.
  • hindered phenol-based antioxidants hindered phenol-based antioxidants, hindered amine-based antioxidants, phosphorus-based antioxidants, and sulfur-based antioxidants are preferable from the viewpoint of achieving both transmittance and sensitivity of the coating film.
  • the antioxidants can be used alone or in combination of two or more.
  • the content of the antioxidant is more preferably 0.5 to 5.0% by mass based on 100% by mass of the solid content of the coloring composition, because the transmittance, spectral characteristics, and sensitivity are good.
  • a leveling agent is preferably added to the colored composition of the present invention for the purpose of improving the coating properties of the composition on a transparent substrate and the drying properties of the colored film.
  • Various surfactants such as silicone surfactants, fluorine surfactants, nonionic surfactants, cationic surfactants and anionic surfactants can be used as the leveling agent.
  • the amount of the surfactant added is preferably 0.001 to 2.0% by mass with respect to the total solid content of the coloring composition of the present invention, and more It is preferably 0.005 to 1.0% by mass. Within this range, the coating properties of the coloring composition, the pattern adhesion, and the transmittance are well balanced.
  • the coloring composition of the present invention may contain only one type of surfactant, or may contain two or more types of surfactants. When two or more types are included, the total amount is preferably within the above range.
  • the coloring composition of the present invention may contain a storage stabilizer in order to stabilize the viscosity of the composition over time.
  • Storage stabilizers include, for example, benzyltrimethyl chloride, quaternary ammonium chloride such as diethylhydroxyamine, organic acids such as lactic acid and oxalic acid and their methyl ethers, t-butylpyrocatechol, tetraethylphosphine, tetraphenylphosphine and the like. organic phosphines, phosphites, and the like.
  • the storage stabilizer can be used in an amount of 0.1 to 10% by mass based on the total amount of the coloring agent (100% by mass).
  • the coloring composition of the present invention may contain an adhesion improver such as a silane coupling agent in order to improve adhesion to the substrate.
  • an adhesion improver such as a silane coupling agent in order to improve adhesion to the substrate.
  • adhesion improvers include vinylsilanes such as vinyltrimethoxysilane and vinyltriethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3- (Meth)acrylsilanes such as methacryloxypropyltriethoxysilane and 3-acryloxypropyltrimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3 -epoxysilanes such as glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane
  • the adhesion improver can be used in an amount of 0.01 to 10 parts by weight, preferably 0.05 to 5 parts by weight, per 100 parts by weight of the colorant in the coloring composition. Within this range, the effect is enhanced and the balance between adhesion, resolution and sensitivity is good, which is more preferable.
  • the coloring composition of the present invention contains a coloring agent, a dispersing agent, a coloring agent carrier such as a binder resin, and/or a solvent, preferably together with a dispersing aid (pigment derivative or surfactant), kneader, two kneaders. It can be produced by finely dispersing using various dispersing means such as a roll mill, three-roll mill, ball mill, horizontal sand mill, vertical sand mill, annular bead mill, or attritor (colorant dispersion). At this time, two or more kinds of colorants and the like may be simultaneously dispersed in the colorant carrier, or separately dispersed in the colorant carrier may be mixed. If the colorant such as dye has high solubility, specifically, if it has high solubility in the solvent to be used, and if it is dissolved by stirring and no foreign matter is confirmed, it is manufactured by finely dispersing as described above. No need.
  • a photosensitive coloring composition when used as a photosensitive coloring composition (resist material), it can be prepared as a solvent-developing or alkali-developing coloring composition.
  • the solvent-developable or alkali-developable colored composition comprises the above-mentioned colorant dispersion, a photopolymerizable monomer and/or a photopolymerizable initiator, and optionally a solvent, other dispersing aids, and additives. It can be adjusted by mixing agents and the like.
  • the photopolymerization initiator may be added at the stage of preparing the coloring composition, or may be added later to the prepared coloring composition.
  • the colored composition of the present invention is separated from coarse particles of 5 ⁇ m or more, preferably 1 ⁇ m or more, more preferably 0.1 ⁇ m or more, by means of centrifugation at a gravitational acceleration of 3000 to 25000 G, filtration with a sintered filter or a membrane filter, or the like. It is preferable to remove coarse particles of 5 ⁇ m or more and mixed dust.
  • the coloring composition preferably does not substantially contain particles of 0.5 ⁇ m or larger. More preferably, it is 0.3 ⁇ m or less.
  • the coloring composition of the present invention preferably has a water content of 0.1 to 2.0% by mass or less relative to the total amount of the coloring composition.
  • the water content is more preferably 0.1 to 1.8% by mass or less, more preferably 0.1 to 1.6% by mass or less, relative to the total amount of the coloring composition. If the content of water is sufficiently small within this range, problems with dispersion stability and sensitivity are less likely to occur even after long-term storage.
  • the method of controlling the water content there are no particular restrictions on the method of controlling the water content, and known methods can be used. Examples thereof include a method of producing a colored composition while blowing in a dry inert gas, and a method of adding molecular sieves and dehydrating after production. Among them, the method of manufacturing while blowing dry inert gas is preferable.
  • the water content can be measured by a known method such as the Karl Fischer method.
  • the coloring composition of the present invention contains metal components containing a small amount of Li, Na, K, Cs, Mg, Ca, Fe, Cr, and Zr (hereinafter also referred to as specific metal atoms) in addition to the constituent components of the colorant. sometimes. If there are many metal components containing these specific metal atoms, storage stability may be inhibited, heat resistance may be lowered, and sensitivity may be lowered when prepared in the form of the above-mentioned photosensitive coloring composition. be. In addition, a color filter prepared using a colored composition containing a large amount of metal components containing such specific metal atoms may generate foreign matter, and as a result, tends to cause a decrease in transmittance.
  • the total content of specific metal atoms in the metal component contained in the coloring composition of the present invention is preferably 1 to 1000 mass ppm with respect to the entire coloring composition.
  • the total amount of specific metal atoms contained in the coloring composition of the present invention is more preferably 300 mass ppm or less, particularly preferably 200 mass ppm or less, relative to the entire coloring composition.
  • the lower limit of the total amount of specific metal atoms is not particularly limited, but is preferably 1 ppm by mass or more, more preferably 5 ppm by mass or more, relative to the entire coloring composition. If it is within the above range, it is possible to obtain a colored composition capable of suppressing costs, excellent in storage stability, and capable of forming a color filter with little generation of foreign matter and reduction in transmittance.
  • the content of each specific metal atom contained in the coloring composition of the present invention is preferably 100 ppm by mass or less, more preferably 50 ppm by mass or less, relative to the entire coloring composition.
  • metal atoms such as Ni, Zn, Cu, Al, Fe, Pt, and Co are included in part of the colorant structure, these metal atoms not forming part of the colorant structure are present. sometimes. The smaller the number of such metal atoms, the better, and they can be removed in the same manner as the specific metal atoms by the following method. Furthermore, it is preferable that the concentration of Mn, Cs, Ti, Si, Pd, and the like mixed in with materials (for example, catalysts) used in the manufacturing process of various raw materials of the coloring composition is low.
  • Various raw materials contained in the coloring composition or methods for removing metal atoms mixed from the apparatus during the manufacturing process include JP 2010-83997, JP 2018-36521, JP 7-198928, JP JP-A-8-333521, JP-A-2009-7432, a method of washing with water, etc., and the method of removing magnetic foreign matter with a magnet described in JP-A-2011-48736, etc., and a single method or a plurality of methods can be used as appropriate. use.
  • the content of specific metal atoms can be measured by inductively coupled plasma emission spectroscopy (ICP).
  • ICP inductively coupled plasma emission spectroscopy
  • the coloring composition of the present invention may contain toluene, and when it contains toluene, the toluene content is preferably 0.1 to 10 mass ppm.
  • the upper limit of the toluene content is preferably 9 mass ppm or less, more preferably 8 mass ppm or less, and even more preferably 7 mass ppm or less.
  • the lower limit is preferably 0.2 ppm by mass or more, more preferably 0.3 ppm by mass or more, and even more preferably 0.4 ppm by mass or more.
  • the color filter of the present invention comprises a red filter segment, a green filter segment and a blue filter segment. Also, the color filter may further comprise a magenta color filter segment, a cyan color filter segment, and a yellow color filter segment.
  • a color filter can be manufactured by a printing method or a photolithography method. Formation of filter segments by a printing method can be patterned simply by repeating printing and drying of a coloring composition prepared as a printing ink, and therefore, as a method for producing color filters, it is low cost and excellent in mass productivity. Furthermore, the development of printing technology has made it possible to print fine patterns with high dimensional accuracy and smoothness. For printing, it is preferable to have a composition that does not allow the ink to dry or solidify on the printing plate or blanket. In addition, it is also important to control the fluidity of the ink on the printing press, and it is also possible to adjust the viscosity of the ink using a dispersant or an extender.
  • the colored composition prepared as the solvent-developable or alkali-developable colored resist material is applied onto the transparent substrate by spray coating, spin coating, slit coating, roll coating, or the like. Depending on the method, the coating is applied so that the dry film thickness is 0.2 to 5 ⁇ m. If necessary, the dried film is exposed (irradiated with radiation) through a mask having a predetermined pattern provided in contact or non-contact with the film. After that, the film is immersed in a solvent or alkaline developer or sprayed with a developer to remove the uncured portion to form a desired pattern, and then the same operation is repeated for other colors to produce a color filter. be able to. Furthermore, in order to promote polymerization of the colored resist material, heating may be applied as necessary. According to the photolithographic method, it is possible to manufacture a color filter with higher accuracy than the printing method.
  • an aqueous solution such as sodium carbonate or sodium hydroxide is used as an alkaline developer, and an organic alkali such as dimethylbenzylamine or triethanolamine can also be used.
  • an antifoaming agent or a surfactant can be added to the developer.
  • a water-soluble or alkaline water-soluble resin such as polyvinyl alcohol or water-soluble acrylic resin is coated and dried to form a film that prevents polymerization inhibition by oxygen. , exposure can also be performed.
  • the color filter of the present invention can be produced by an electrodeposition method, a transfer method, an inkjet method, etc. in addition to the above methods, and the colored composition of the present invention can be used in any method.
  • the electrodeposition method is a method of manufacturing a color filter by using a transparent conductive film formed on a substrate to electrodeposit each color filter segment on the transparent conductive film by electrophoresis of colloidal particles.
  • the transfer method is a method in which filter segments are formed in advance on the surface of a removable transfer base sheet, and the filter segments are transferred to a desired substrate.
  • a black matrix can be formed in advance before forming each color filter segment on the transparent substrate or the reflective substrate.
  • a multilayer film of chromium or chromium/chromium oxide, an inorganic film such as titanium nitride, or a resin film in which a light shielding agent is dispersed can be used, but is not limited to these.
  • thin film transistors (TFTs) may be formed in advance on the transparent substrate or reflective substrate, and then each color filter segment may be formed.
  • An overcoat film, a transparent conductive film, and the like are formed on the color filter of the present invention, if necessary.
  • the color filter of the present invention can also be used for manufacturing color liquid crystal display devices, color solid-state imaging devices, organic EL display devices, quantum dot display devices, electronic paper, and the like.
  • the sensor of the invention comprises the color filter segment of the invention.
  • the configuration of the sensor of the present invention is a configuration provided with the color filter segment of the present invention, and is not particularly limited as long as it functions as a sensor. Examples of the configuration include the following.
  • a plurality of photodiodes constituting a light receiving area of a solid-state imaging device (CCD sensor, CMOS sensor, organic CMOS sensor, etc.) and transfer electrodes made of polysilicon or the like are provided on a substrate, and on the photodiodes and the transfer electrodes, A light shielding film made of tungsten or the like with an opening only in the light receiving portion of the photodiode, 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 light receiving portion of the photodiode, It is a configuration having the color filter of the present invention on the device protective film.
  • the organic CMOS sensor includes a thin panchromatic photosensitive organic photoelectric conversion film as a photoelectric conversion layer and a CMOS signal readout substrate. It is a two-layered hybrid structure in which inorganic materials play the role of extracting signals to the outside, and in principle, it is possible to achieve an aperture ratio of 100% for incident light.
  • the organic photoelectric conversion film is a structure-free continuous film and can be laid on a CMOS signal readout substrate, it does not require an expensive microfabrication process and is suitable for miniaturization of filter segments.
  • Arrangement of the color filters is not particularly limited, and a known method can be used.
  • the acid value of the resin-type dispersant and the binder resin was obtained by potentiometric titration using a 0.1N potassium hydroxide/ethanol solution.
  • the acid value of the resin-type dispersant and binder resin indicates the acid value of the non-volatile matter.
  • Binder resin, weight average molecular weight (Mw) of resin type dispersant The weight average molecular weight (Mw) of the resin is measured using a TSKgel column (manufactured by Tosoh Corporation) and equipped with an RI detector (manufactured by Tosoh Corporation, HLC-8120GPC) using THF as a developing solvent. Weight average molecular weight (Mw).
  • MALDI TOF-MS spectra were used to identify the compounds used in the present invention.
  • the MALDI TOF-MS spectrum was obtained using a MALDI mass spectrometer autoflex III manufactured by Bruker Daltonics, and the obtained compound was identified by matching the molecular ion peak of the mass spectrum obtained in the negative mode with the mass number obtained by calculation. identified.
  • the amount of the specific metal atom in the coloring composition was measured with an ICP emission spectrometer Varian 720-ES manufactured by Agilent Technologies after decomposing the powder obtained by drying the coloring composition at 180° C. with microwaves.
  • resin type dispersant solution 1 10 parts of methacrylic acid, 20 parts of methyl methacrylate, 90 parts of 2-methoxyethyl methacrylate, 40 parts of tert-butyl methacrylate, 20 parts of n-butyl acrylate, tert- 20 parts of butyl acrylate and 50 parts of propylene glycol monomethyl ether acetate were charged, and the atmosphere was purged with nitrogen gas. The inside of the reaction vessel was heated to 50° C. with stirring, and 12 parts of 3-mercapto-1,2-propanediol was added.
  • Example 1 (Production of diketopyrrolopyrrole pigment (1-1)) 200 parts of tert-amyl alcohol dehydrated with molecular sieves and 153.8 parts of sodium-tert-amyl alkoxide are added to a stainless steel reaction vessel equipped with a reflux tube under a nitrogen atmosphere, and heated to 100° C. with stirring to form an alcoholate. A solution was prepared. On the other hand, 100 parts of tert-amyl alcohol dehydrated with molecular sieves, 84.7 parts of diisopropyl succinate, and 100 parts of benzonitrile compound (1) were added to a glass flask and heated to 90°C with stirring to dissolve.
  • a solution of a mixture of A heated solution of this mixture was uniformly added dropwise to the above alcoholate solution heated to 100° C. over 2 hours with vigorous stirring. After the dropwise addition was completed, heating and stirring were continued at 90° C. for 2 hours to obtain an alkali metal salt of a diketopyrrolopyrrole compound. Further, 300 parts of methanol, 1200 parts of water, and 304 parts of acetic acid were added to a glass jacketed reaction vessel and cooled to -10°C. This cooled mixture was cooled to 75° C. while rotating a shear disk with a diameter of 8 cm at 4000 rpm using a high-speed stirring disperser. The solution was added in small portions.
  • the rate of adding the alkali metal salt of the diketopyrrolopyrrole compound at 75 ° C. while cooling so that the temperature of the mixture consisting of methanol, acetic acid, and water is always kept at -5 ° C. or less. was added in portions over approximately 120 minutes, adjusting the .
  • the resulting red suspension was filtered at 5° C. and washed with 500 parts of methanol and 2000 parts of water to obtain a red paste. This paste was redispersed in 1,600 parts of methanol cooled to 0° C. and 1,600 parts of water, and stirred at 5° C. for 3 hours.
  • Examples 2 to 40 (Production of diketopyrrolopyrrole pigments (1-2 to 40))
  • the benzonitrile compound (1) was changed to a benzonitrile compound of the following general formula (5) in which Z 1 is a substituent listed in Table 2, and diisopropyl succinate and sodium -tert-amyl alkoxide were added in the amounts listed in Table 2 below.
  • Diketopyrrolopyrrole pigments (1-2 to 40) were obtained in the same manner as in Example 1, except that the
  • Example 41 (Production of micronized diketopyrrolopyrrole pigment (2-1)) A mixture of 100 parts of diketopyrrolopyrrole pigment (1-1), 1000 parts of sodium chloride and 120 parts of diethylene glycol was kneaded at 60° C. for 6 hours using a stainless steel 1-gallon kneader (Inoue Seisakusho). Next, this kneaded product was put into 5 liters of hot water and stirred for 1 hour while being heated to 70° C. to form a slurry. After filtration, washing with 6 L of water was repeated three times to remove sodium chloride and diethylene glycol, followed by drying and pulverization to obtain 95 parts of finely divided diketopyrrolopyrrole pigment (2-1).
  • Example 42 to 80 (Production of finely divided diketopyrrolopyrrole pigments (2-2 to 40)) Fine diketopyrrolopyrrole pigments (2-2 to 40) were obtained in the same manner as in Example 41, except that the diketopyrrolopyrrole pigment (1-1) was changed to (1-2 to 40). .
  • Example 82 (Preparation of finely divided pigment composition (P-2)) A finely divided pigment composition (P-2) was obtained in the same manner as in Example 81, except that the dye derivative A was changed to the dye derivative B.
  • Example 83 (Preparation of finely divided pigment composition (P-3)) A finely divided pigment composition (P-3) was obtained in the same manner as in Example 81, except that dye derivative A was changed to dye derivative C.
  • Micronized diketopyrrolopyrrole pigment (2-1) 12.6 parts Dye derivative A 0.7 parts Dye derivative B 0.7 parts Resin type dispersant solution 1 12.0 parts Binder resin solution 1 6.0 parts Propylene glycol Monomethyl ether acetate 68.0 parts With respect to the entire coloring composition (RP-1), the water content was 1.1%, and the total content of specific metal atoms was 190 ppm.
  • Example 145 (Preparation of coloring composition (RP-45)) After stirring and mixing the following mixture uniformly, using zirconia beads with a diameter of 0.5 mm, after dispersing for 5 hours with an Eiger mill (manufactured by Eiger Japan Co., Ltd. "Mini Model M-250 MKII"), 5.0 ⁇ m to prepare a coloring composition (RP-45).
  • Micronized diketopyrrolopyrrole pigment (2-9) 12.6 parts Dye derivative A 0.7 parts Dye derivative B 0.7 parts Resin type dispersant solution 1 12.0 parts Binder resin solution 1 6.0 parts Propylene glycol Monomethyl ether acetate 67.0 parts Ion-exchanged water 1.0 parts With respect to the entire coloring composition (RP-45), the water content was 2.4%, and the total amount of specific metal atoms was 190 ppm.
  • Example 146 (Preparation of coloring composition (RP-46)) A molecular sieve was added to the coloring composition (RP-9), and the mixture was allowed to stand for 24 hours and filtered to obtain a coloring composition (RP-46). The water content was 0.4% and the total amount of specific metal atoms was 170 ppm with respect to the entire coloring composition (RP-46).
  • micronized diketopyrrolopyrrole pigment (2-9) (Purification 2 of micronized diketopyrrolopyrrole pigment (2-9)) In the production of micronized diketopyrrolopyrrole pigment (2-9), the same operation as in Example 1 was performed, except that washing with 6 L of water three times was changed to washing with 6 L of deionized water three times.
  • Example 147 (Preparation of coloring composition (RP-47)) Same as the coloring composition (RP-9), except that the micronized diketopyrrolopyrrole pigment (2-9) was changed to the compound obtained in Purification 1 of the micronized diketopyrrolopyrrole pigment (2-9) to obtain a coloring composition (RP-47).
  • the water content was 1.5% and the total amount of specific metal atoms was 1030 ppm with respect to the entire coloring composition (RP-47).
  • Example 148 (Preparation of coloring composition (RP-48)) Same as the coloring composition (RP-9), except that the micronized diketopyrrolopyrrole pigment (2-9) was changed to the compound obtained in Purification 2 of the micronized diketopyrrolopyrrole pigment (2-9) to obtain a coloring composition (RP-48).
  • the water content was 1.0% and the total amount of specific metal atoms was 60 ppm with respect to the entire coloring composition (RP-48).
  • the coloring composition using the diketopyrrolopyrrole pigment of the present invention exhibits excellent dispersion stability.
  • Example 201 (Preparation of photosensitive coloring composition (RR-1)) The following mixture was uniformly stirred and mixed, and then filtered through a 1 ⁇ m filter to prepare a photosensitive coloring composition (RR-1). The mixing ratio of the coloring composition (RP-1) and the coloring composition (YP-1) was adjusted so that the transmittance at 530 nm of the coating film was 5% when the transmittance at 400 nm was 5%.
  • Coloring composition (RP-1) and coloring composition (YP-1) total 72.86 parts binder resin solution 1 1.40 parts photopolymerizable monomer (manufactured by Toagosei Co., Ltd. "Aronix M-402”) 1 .70 parts Photopolymerization initiator (manufactured by BASF "IRGACURE OXE-02”) 0.17 parts Propylene glycol monomethyl ether acetate 23.87 parts
  • Example 202 to 248, Comparative Examples 201 to 203 (Preparation of photosensitive coloring composition (RR-2 to 51))
  • the coloring composition (RP-1) was changed to the coloring composition shown in Table 5, and the coloring composition (YP- 1) to prepare a photosensitive coloring composition (RR-2 to 51) in the same manner as in Example 201, except that the mixing ratio was changed.
  • ⁇ Dispersion stability evaluation> The dispersion stability of the resulting photosensitive coloring composition was measured in the same manner as for the dispersion stability of the coloring composition, and evaluated in three stages according to the following criteria.
  • the resulting photosensitive coloring composition was coated on a 6-inch glass wafer with a flattening film resist solution (HL-18s: manufactured by Nippon Steel Chemical Co., Ltd.) by spin coating, and pre-baked at 100 ° C. hot.
  • the plate was heat treated for 6 minutes. Further, the coated film was cured in an oven at 230° C. for 1 hour to form a 1.0 ⁇ m flattening film to obtain a wafer with a flattening film.
  • the resulting resist material was applied onto a flattening film-attached glass wafer by a spin coater, and pre-baked by heat treatment on a hot plate at 100° C. for 1 minute.
  • ⁇ film thickness is less than 0.55 ⁇ m ⁇ : film thickness is 0.55 ⁇ m or more and less than 0.60 ⁇ m ⁇ : film thickness is 0.60 ⁇ m or more
  • Transmittance evaluation> The transmittance of the previous coating film was evaluated in three grades according to the following criteria. ⁇ : Transmittance at 600 nm is 90% or more ⁇ : Transmittance at 600 nm is 85% or more and less than 90% ⁇ : Transmittance at 600 nm is less than 85%
  • Table 5 shows the evaluation results of the photosensitive coloring composition.
  • the diketopyrrolopyrrole pigment of the present invention makes it possible to obtain a photosensitive coloring composition exhibiting excellent coloring power, transmittance and dispersion stability.

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Abstract

La présente invention a pour but de procurer un pigment de dicétopyrrolopyrrole présentant à la fois un pouvoir colorant élevé et une transmittance élevée en tant que colorant rouge, et présentant en outre une excellente stabilité de dispersion. En outre, la présente invention a pour but de procurer une composition pigmentaire utilisant ledit pigment, une composition colorée, un filtre de couleur et un capteur. La solution selon l'invention consiste en un pigment de dicétopyrrolopyrrole de formule générale (1). <sp /> <sp />[Dans la formule générale (1), un 1 et un 2 sont chacun indépendants et représentent un cycle à cinq ou six chaînons qui peut avoir un groupe substitué, et les atomes formant le cycle sont chacun indépendants et peuvent être des atomes de carbone, des atomes d'oxygène ou des atomes de soufre. <sp /> <sp />R1 et R2 sont chacun indépendants et représentent des atomes d'hydrogène, un groupe alkyle ayant de 1 à 10 atomes de carbone qui peut avoir un groupe substitué, ou des atomes d'halogène.]
PCT/JP2023/005890 2022-03-02 2023-02-20 Pigment de dicétopyrrolopyrrole, composition de pigment, composition colorée, filtre de couleur et capteur WO2023167026A1 (fr)

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JP2022031825A JP2023127878A (ja) 2022-03-02 2022-03-02 ジケトピロロピロール顔料、顔料組成物、着色組成物、カラーフィルタおよびセンサ

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08245897A (ja) * 1994-11-04 1996-09-24 Ciba Geigy Ag 黄色ジケトピロロピロール顔料
JP2001097975A (ja) * 1999-09-27 2001-04-10 Ciba Specialty Chem Holding Inc 蛍光ジケトピロロピロール
JP2011046851A (ja) * 2009-08-28 2011-03-10 Toyo Ink Mfg Co Ltd 低分子塗布型有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子用インキ組成物、および、有機エレクトロルミネッセンス素子
JP2016510052A (ja) * 2013-03-06 2016-04-04 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 新規な複素環式蛍光染料及びその製造方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08245897A (ja) * 1994-11-04 1996-09-24 Ciba Geigy Ag 黄色ジケトピロロピロール顔料
JP2001097975A (ja) * 1999-09-27 2001-04-10 Ciba Specialty Chem Holding Inc 蛍光ジケトピロロピロール
JP2011046851A (ja) * 2009-08-28 2011-03-10 Toyo Ink Mfg Co Ltd 低分子塗布型有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子用インキ組成物、および、有機エレクトロルミネッセンス素子
JP2016510052A (ja) * 2013-03-06 2016-04-04 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 新規な複素環式蛍光染料及びその製造方法

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