WO2012102399A1 - Composition de pigments du type dicétopyrrolopyrrole pour filtres couleur, composition colorée pour filtres couleur et filtre couleur - Google Patents

Composition de pigments du type dicétopyrrolopyrrole pour filtres couleur, composition colorée pour filtres couleur et filtre couleur Download PDF

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Publication number
WO2012102399A1
WO2012102399A1 PCT/JP2012/051888 JP2012051888W WO2012102399A1 WO 2012102399 A1 WO2012102399 A1 WO 2012102399A1 JP 2012051888 W JP2012051888 W JP 2012051888W WO 2012102399 A1 WO2012102399 A1 WO 2012102399A1
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Prior art keywords
pigment
formula
composition
parts
diketopyrrolopyrrole
Prior art date
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PCT/JP2012/051888
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English (en)
Japanese (ja)
Inventor
裕介 飯田
雅之 藤木
安藤　宗徳
山本　裕一
和久　寿男
悠太 阿部
久満 荒川
香苗 笹木
Original Assignee
東洋インキＳｃホールディングス株式会社
トーヨーケム株式会社
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Priority claimed from JP2011015874A external-priority patent/JP5659823B2/ja
Priority claimed from JP2011076928A external-priority patent/JP5724537B2/ja
Priority claimed from JP2011076929A external-priority patent/JP5760596B2/ja
Application filed by 東洋インキＳｃホールディングス株式会社, トーヨーケム株式会社 filed Critical 東洋インキＳｃホールディングス株式会社
Priority to KR1020137020929A priority Critical patent/KR101920285B1/ko
Priority to KR1020187020266A priority patent/KR101942407B1/ko
Priority to CN201280006727.XA priority patent/CN103339536B/zh
Priority to KR1020187035854A priority patent/KR101971251B1/ko
Publication of WO2012102399A1 publication Critical patent/WO2012102399A1/fr

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    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
    • C—CHEMISTRY; METALLURGY
    • 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
    • C09B57/004—Diketopyrrolopyrrole 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
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0002—Grinding; Milling with solid grinding or milling assistants
    • 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
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0022—Wet grinding of pigments
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0034—Mixtures of two or more pigments or dyes of the same type
    • C09B67/0039—Mixtures of diketopyrrolopyrroles
    • 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
    • C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/031—Organic compounds not covered by group G03F7/029
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers

Definitions

  • the present invention relates to a diketopyrrolopyrrole pigment composition for a color filter, a coloring composition for a color filter, and a color filter formed using the same.
  • a liquid crystal layer sandwiched between two polarizing plates controls the amount of light passing through the first polarizing plate by controlling the degree of polarization of light passing through the first polarizing plate.
  • the type using twisted nematic (TN) type liquid crystal is the mainstream.
  • a color filter is a surface of a transparent substrate such as glass, in which two or more kinds of fine band (striped) filter segments of different hues are arranged in parallel or crossing each other, or fine filter segments are arranged vertically and horizontally. It is made up of those arranged in In general, it is often formed from filter segments of three colors of red, green, and blue. Each of these segments is as fine as, for example, several microns to several hundreds of microns, and is arranged neatly in a predetermined arrangement for each hue. Has been.
  • a transparent electrode for driving a liquid crystal is formed on a color filter by vapor deposition or sputtering, and an alignment film for aligning the liquid crystal in a certain direction is further formed thereon.
  • high-temperature treatment is generally performed at 200 ° C. or higher, preferably 230 ° C. or higher in the manufacturing process for forming the color filter.
  • the color filter manufacturing method is mainly a method called a pigment dispersion method using a pigment having excellent light resistance and heat resistance as a colorant.
  • a pigment having excellent light resistance and heat resistance such as a diketopyrrolopyrrole pigment, an anthraquinone pigment, a perylene pigment or a disazo pigment, may be used alone or in combination for the red filter segment. It is common.
  • C.I. I. Pigment Red 254 is a pigment that is particularly excellent in brightness, but further improvement in brightness is desired.
  • C.I. I. Pigment Red 254 is a pigment that is particularly excellent in brightness, but further improvement in brightness is desired.
  • the diketopyrrolopyrrole pigments that have been refined have the property of being easy to grow crystals due to their intermolecular hydrogen bonds, crystallization occurs in the heating process when forming the color filter, and foreign matter is generated. Is a problem.
  • the diketopyrrolopyrrole pigment can be obtained by the production method disclosed in Patent Document 1 and Patent Document 2 (hereinafter referred to as “succinic acid ester synthesis method”).
  • Patent Document 3 discloses a method of obtaining a mixture of at least two structurally different diketopyrrolopyrrole pigments using a plurality of nitrile compounds as raw materials in a succinate synthesis method.
  • Patent Document 4 a mixture of at least two structurally different diketopyrrolopyrrole pigments obtained by a succinate synthesis method using a nitrile compound having a plurality of specific structural formulas as a raw material is used for a color filter. It is described to do.
  • Patent Document 5 a diketopyrrolopyrrole pigment (mainly CI Pigment Red 254), a diaryl diketopyrrolopyrrole compound having at least one specific structural formula, and a pigment derivative are combined.
  • Patent Document 7 discloses a coloring composition for a color filter using a brominated diketopyrrolopyrrole pigment.
  • Patent Document 8 describes that a brominated diketopyrrolopyrrole pigment composition is used for a color filter.
  • JP 58-210084 A Japanese Patent Application Laid-Open No. 07-90189 JP-A-61-120861 Special table 2007-514798 gazette WO2009 / 081930 pamphlet JP 2009-149707 A JP 1999-231516 A WO2009 / 144115 pamphlet
  • a diketopyrrolopyrrole pigment composition for a color filter which has good brightness and contrast, and is less likely to cause crystal precipitation of a diketopyrrolopyrrole pigment even in a heating process, for a color filter It is in providing a coloring composition and a color filter using the same.
  • a first embodiment of the present invention is a diketopyrrolopyrrole pigment represented by formula (1) and a diketopyrrolopyrrole pigment for color filters containing the diketopyrrolopyrrole pigment represented by formula (A-2)
  • the content of the diketopyrrolopyrrole pigment represented by the formula (A-2) is 1% by mass to 15% by mass based on the total mass of the diketopyrrolopyrrole pigment.
  • the present invention relates to a characteristic diketopyrrolopyrrole pigment composition for color filters.
  • a and B are each independently a hydrogen atom, a fluorine atom, an iodine atom, a cyano group, an alkyl group having 1 to 12 carbon atoms, an optionally substituted phenyl group, —CF 3 , —OR 1 , —SR 2 , —N (R 3 ) R 4 , —COOR 5 , —CONH 2 , —CONHR 6 , —CON (R 7 ) R 8 , —SO 2 NH 2 , —SO 2 NHR 9 , or —SO 2 N (R 10 ) R 11 , R 1 to R 11 are each independently an alkyl group having 1 to 12 carbon atoms, a phenyl group which may have a substituent, or an aralkyl group which may have a substituent.
  • a and B are not hydrogen atoms at the same time.
  • the diketopyrrolopyrrole pigment represented by the formula (A-2) is represented by the formula (A-2-1), the formula (A-2-2), the formula (A-2). -3) or the formula (A-2-4), the diketopyrrolopyrrole pigment composition for color filters.
  • R 6 to R 8 are each independently an alkyl group having 1 to 12 carbon atoms or an optionally substituted phenyl group.
  • the first embodiment further includes C.I. as a diketopyrrolopyrrole pigment.
  • C.I. as a diketopyrrolopyrrole pigment.
  • the present invention relates to the above-mentioned diketopyrrolopyrrole pigment composition for color filters, which contains CI Pigment Red 254.
  • the first embodiment is based on the total mass of the diketopyrrolopyrrole pigment, and the diketopyrrolopyrrole pigment represented by the formula (1) and C.I. I.
  • the first embodiment includes a diketopyrrolopyrrole pigment represented by the formula (1) and C.I. I.
  • the present invention relates to the above diketopyrrolopyrrole pigment composition for color filters, wherein the mass ratio of Pigment Red 254 is 20:80 to 99: 1.
  • the first embodiment further relates to the above-mentioned diketopyrrolopyrrole pigment composition for color filters, which further contains a dye derivative.
  • the second embodiment of the present invention is a diketopyrrolopyrrole pigment represented by formula (1) and a diketopyrrolopyrrole pigment for color filters containing the diketopyrrolopyrrole pigment represented by formula (B-2).
  • the present invention relates to a diketopyrrolopyrrole pigment composition for color filters, wherein the mass ratio of the formula (1) to the formula (B-2) is 97: 3 to 85:15.
  • a and B are each independently a hydrogen atom, a fluorine atom, a chlorine atom, an iodine atom, a cyano group, an alkyl group having 1 to 12 carbon atoms, an optionally substituted phenyl group, —CF 3 , — OR 1 , —SR 2 , —N (R 3 ) R 4 , —COOR 5 , —CONH 2 , —CONHR 6 , —CON (R 7 ) R 8 , —SO 2 NH 2 , —SO 2 NHR 9 , or , —SO 2 N (R 10 ) R 11 , R 1 to R 11 are each independently an alkyl group having 1 to 12 carbon atoms, a phenyl group which may have a substituent, or an aralkyl group which may have a substituent.
  • a and B are not hydrogen atoms at the same time.
  • the above formula (B-2) is represented by formula (B-2-1), formula (B-2-2), formula (B-2-3), formula (B-2). -4), the formula (B-2-5), the formula (B-2-6), or the formula (B-2-7), wherein the diketopyrrolopyrrole system for color filters
  • the present invention relates to a pigment composition.
  • R 12 to R 15 are each independently an alkyl group having 1 to 12 carbon atoms or an optionally substituted phenyl group.
  • the second embodiment further relates to the above-mentioned diketopyrrolopyrrole pigment composition for color filters, which further contains a dye derivative.
  • a third embodiment of the present invention is a coloring composition containing a colorant, a binder resin, and an organic solvent, wherein the colorant contains the diketopyrrolopyrrole pigment composition of the first embodiment.
  • the present invention relates to a colored composition for a color filter.
  • the third embodiment further relates to the above color filter coloring composition, further comprising a photopolymerizable monomer and / or a photopolymerization initiator.
  • a fourth embodiment of the present invention is a coloring composition containing a colorant, a binder resin, and an organic solvent, wherein the colorant contains the diketopyrrolopyrrole pigment composition of the second embodiment.
  • the present invention relates to a colored composition for a color filter.
  • the fourth embodiment further relates to the above color filter coloring composition, further comprising a photopolymerizable monomer and / or a photopolymerization initiator.
  • a fifth embodiment of the present invention is a color filter coloring composition
  • a color filter coloring composition comprising a pigment (A), a binder resin (CB), and a solvent, wherein the pigment (A) is represented by the formula (1):
  • the present invention relates to a coloring composition for a color filter, which comprises the pigment (A1) shown, and the binder resin (CB) contains an alkali-soluble photosensitive resin (C-B1).
  • the pigment (A) is a diketopyrrolopyrrole pigment other than the pigment (A1), an azo pigment, an anthraquinone pigment, a perylene pigment, a quinacridone pigment, or a benzimidazolone pigment. And at least one selected from the group consisting of quinoline pigments.
  • the fifth embodiment further includes at least one photopolymerization initiator (CD) selected from the group consisting of acetophenone compounds, phosphine compounds, imidazole compounds, and oxime ester compounds. And a coloring composition for a color filter.
  • CD photopolymerization initiator
  • a sixth embodiment of the present invention is a color filter coloring composition
  • a color filter coloring composition comprising a pigment (A), a binder resin (DB), and a solvent, wherein the pigment (A) is represented by the formula (1):
  • a coloring composition for a color filter characterized in that the binder resin (DB) contains a resin (D-B1) having structural units (D-b1) to (D-b3).
  • R represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms which may have a benzene ring.
  • the broken line in formula (D-3) represents a cyclic structure containing one or more saturated or unsaturated heterocycles which may have a substituent, adjacent to the benzene ring.
  • the pigment (A) is a diketopyrrolopyrrole pigment other than the pigment (A1), an azo pigment, an anthraquinone pigment, a perylene pigment, a quinacridone pigment, or a benzimidazolone pigment. And at least one selected from the group consisting of quinoline pigments.
  • the sixth embodiment further includes at least one photopolymerization initiator (DD) selected from the group consisting of acetophenone compounds, phosphine compounds, imidazole compounds, and oxime ester compounds. And a coloring composition for a color filter.
  • DD photopolymerization initiator
  • a seventh embodiment of the present invention relates to a color filter comprising a filter segment formed from the color filter coloring composition.
  • CI means a color index (CI).
  • CI color index
  • (meth) acrylate when expressed as “(meth) acrylate”, “(meth) acrylic acid”, or “(meth) acrylamide”, “acrylate and / or methacrylate”, “acrylic acid”, respectively, unless otherwise specified.
  • a first embodiment includes a diketopyrrolopyrrole pigment represented by the following formula (1) and a diketo for color filter containing a specific heterodiketopyrrolopyrrole pigment represented by the following formula (A-2):
  • a pyrrolopyrrole pigment composition wherein the content of the specific heterodiketopyrrolopyrrole pigment represented by the following formula (A-2) is 1% by mass to 15% based on the total mass of the diketopyrrolopyrrole pigment. It is a diketopyrrolopyrrole pigment composition for color filters that is mass%.
  • C.I. I It has been found that the brightness is improved by applying a brominated diketopyrrolopyrrole pigment (formula (1)) to a color filter as compared with CI Pigment Red 254 (chlorinated diketopyrrolopyrrole pigment). Further, a diketopyrrolopyrrole pigment containing a diketopyrrolopyrrole pigment (formula (A-2) (hereinafter referred to as “specific heterodiketopyrrolopyrrole pigment A”) having a specific structure and an asymmetric substituent introduced.
  • the composition a color filter having not only high brightness but also high contrast and crystal precipitation caused by a heating process can be obtained.
  • the specific hetero diketopyrrolopyrrole pigment A selected here is Since the interaction with the resin component is small, the active surface of the brominated diketopyrrolopyrrole pigment can be efficiently covered, and the thermal aggregation of the pigment due to the heating process is suppressed, so the contrast is increased with a small amount of content, In addition, the specific heterodiketopyrrolopyrrole pigment A has better color characteristics than the known crystal precipitation inhibitors.
  • the addition amount can be reduced, the excellent brightness improvement effect of the brominated diketopyrrolopyrrole pigment is not impaired, and the diketopyrrolopyrrole pigment composition contains the specific hetero diketopyrrolopyrrole pigment A. Therefore, it is excellent in viscosity stability.
  • the diketopyrrolopyrrole color filter for color filters has good brightness and contrast, does not cause crystal precipitation of the diketopyrrolopyrrole pigment even in the heating step, and has excellent viscosity stability.
  • a pigment composition can be provided.
  • a and B are each independently a hydrogen atom, a fluorine atom, an iodine atom, a cyano group, an alkyl group having 1 to 12 carbon atoms, an optionally substituted phenyl group, —CF 3 , —OR 1 , —SR 2 , —N (R 3 ) R 4 , —COOR 5 , —CONH 2 , —CONHR 6 , —CON (R 7 ) R 8 , —SO 2 NH 2 , —SO 2 NHR 9 , or —SO 2 N (R 10 ) R 11 , R 1 to R 11 are each independently an alkyl group having 1 to 12 carbon atoms, a phenyl group which may have a substituent, or an aralkyl group which may have a substituent.
  • a and B are not hydrogen atoms at the same time.
  • the alkyl group having 1 to 12 carbon atoms may be linear or branched, and specifically includes methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl.
  • Examples of the phenyl group which may have a substituent include an alkyl group having 1 to 4 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. And a phenyl group having a substituent such as a group. The phenyl group may have one or more of these substituents.
  • phenyl group More specifically, 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 thereof include, but are not limited to, a phenyl group.
  • Examples of the aralkyl group which may have a substituent include an alkyl group having 1 to 4 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. And an aralkyl group having a substituent such as a group. The aralkyl group may have one or more of these substituents.
  • benzyl group 4-methylbenzyl group, 4-tert-butylbenzyl group, 4-methoxybenzyl group, 4-nitrobenzyl group, 2,4-dichlorobenzyl group and the like can be mentioned. It is not limited.
  • the formulas (A-2-1) and (A-2-2) ), Formula (A-2-3), and Formula (A-2-4) are preferable from the viewpoints of brightness, contrast, and crystal precipitation suppression effect.
  • R 6 to R 8 in the formulas (A-2-3) and (A-2-4) are an alkyl group having 4 or more carbon atoms, or a phenyl group which may have a substituent. It is preferable from the point of the crystal precipitation inhibitory effect.
  • the reason for these being effective in increasing contrast and suppressing crystal precipitation is because of steric hindrance due to bulky substituents such as carboamide groups (carbamoyl groups), phenyl groups, and t-butyl groups having an alkyl group having 4 or more carbon atoms. It is considered that the aggregation of the pigment is suppressed by the effect.
  • the specific hetero diketopyrrolopyrrole pigment A having a carboamide group (carbamoyl group), a phenyl group, and a t-butyl group has excellent color characteristics, so that the excellent lightness of the brominated diketopyrrolopyrrole pigment is impaired. There is nothing.
  • R 6 to R 8 are each independently an alkyl group having 1 to 12 carbon atoms or an optionally substituted phenyl group.
  • the content of the specific heterodiketopyrrolopyrrole pigment A represented by the formula (A-2) is in the range of 1% by mass to 15% by mass based on the total weight of the diketopyrrolopyrrole pigment. It is characterized by being. Preferably, it is in the range of 3% by mass to 10% by mass.
  • the ratio of the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2) exceeds 15% by mass, an effect of suppressing crystal precipitation can be obtained, but the brominated diketopyrrolopyrrole pigment of the formula (1) is excellent. Lightness will be impaired.
  • the ratio of the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2) is less than 1% by mass, the effects of increasing the contrast and suppressing the crystal precipitation are not sufficient.
  • the crystal precipitation suppressing effect is not sufficient, light scattering occurs due to the crystalline foreign matter deposited on the surface of the coating film in the heating step, causing a decrease in brightness and contrast ratio. Therefore, by using the diketopyrrolopyrrole pigment composition containing the specific heterodiketopyrrolopyrrole pigment A in the above-mentioned ratio, high brightness and high contrast are achieved, and the diketopyrrolopyrrole pigment is also heated by the heating process. Crystal precipitation can be suppressed. Furthermore, excellent viscosity stability can be obtained.
  • the pigment composition contains a diketopyrrolopyrrole pigment of the formula (1) and a diketopyrrolopyrrole pigment other than the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2) as long as the effect is not impaired. You may use together.
  • examples thereof include, but are not limited to, diketopyrrolopyrrole pigments such as CI Pigment Orange 71, 73, or 81.
  • Examples of diketopyrrolopyrrole pigments that can be used in combination include C.I. I. Pigment Red 254 is preferred.
  • Pigment Red 254 is preferred because it is usually contained when the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2) is produced by the succinic acid diester synthesis method, and the diketo of the formula (1) This is because the excellent lightness of the pyrrolopyrrole pigment is hardly affected.
  • the pigment composition is C.I. I.
  • the total content of CI Pigment Red 254 is preferably 85% by mass to 99% by mass.
  • the total content with Pigment Red 254 is less than 85% by mass, the effect of improving brightness may be reduced.
  • the total content is more than 99% by mass, the content of the specific heterodiketopyrrolopyrrole pigment A is small. The contrast ratio and the effect of suppressing crystal precipitation may not be sufficiently obtained.
  • diketopyrrolopyrrole pigment represented by the formula (1) and C.I. I The mass ratio of Pigment Red 254 is preferably 20:80 to 99: 1. More preferably, it is 50:50 to 99: 1.
  • a diketopyrrolopyrrole pigment represented by formula (1) and C.I. I. When the content of the diketopyrrolopyrrole pigment represented by the formula (1) in the total of the pigment red 254 is 20% by mass or more, it is preferable because the effect of improving the brightness is increased.
  • the mass ratio of the diketopyrrolopyrrole pigment of formula (1) and the specific heterodiketopyrrolopyrrole pigment B of formula (B-2) is preferably 97: 3 to 85:15.
  • the diketopyrrolopyrrole pigment represented by the formula (1) can be obtained by using a known method described in International Publication No. 2009/144115 pamphlet or the like.
  • the diketopyrrolopyrrole pigment represented by the formula (1) can be produced by a succinic acid diester synthesis method. That is, 2 mol of 4-bromobenzonitrile per 1 mol of 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 at a high temperature of 80 to 110 ° C. A condensation reaction is performed to produce an alkali metal salt of a diketopyrrolopyrrole compound.
  • a brominated diketopyrrolopyrrole pigment can be obtained by protonating the alkali metal salt of the diketopyrrolopyrrole compound with water, alcohol, acid or the like.
  • the size of the primary particle diameter obtained can be controlled by the temperature in protonation, the type, ratio and amount of water, alcohol or acid.
  • the manufacturing method of the diketopyrrolopyrrole pigment represented by Formula (1) is not limited to this method.
  • Specific heterodiketopyrrolopyrrole pigment A of the formula (A-2) is described in, for example, the document Synth. Commun. 1988, 18, 1213 and Tetrahedron, 58 (2002) 5547-5565.
  • the method for producing the specific heterodiketopyrrolopyrrole pigment A is not limited to this method.
  • the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2) is C.I. I. It can also be synthesized as a mixture with Pigment Red 254. This can be achieved by using a method using at least two structurally different benzonitrile compounds in the succinic acid diester synthesis method (hereinafter referred to as “succinic acid diester co-synthesis method”). Specifically, in the method described in the pamphlet of WO2009 / 081930, a plurality of benzonitrile compounds to be used are selected from 4-chlorobenzonitrile and a benzonitrile compound represented by the following formula (A-3).
  • the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2) I. It can be manufactured as a mixture with Pigment Red 254.
  • a and B are each independently a hydrogen atom, a fluorine atom, an iodine atom, a cyano group, an alkyl group having 1 to 12 carbon atoms, an optionally substituted phenyl group, —CF 3 , —OR 1 , —SR 2 , —N (R 3 ) R 4 , —COOR 5 , —CONH 2 , —CONHR 6 , —CON (R 7 ) R 8 , —SO 2 NH 2 , —SO 2 NHR 9 , or —SO 2 N (R 10 ) R 11 , R 1 to R 11 are each independently an alkyl group having 1 to 12 carbon atoms, a phenyl group which may have a substituent, or an aralkyl group which may have a substituent.
  • a and B are not hydrogen atoms at the same time.
  • the alkyl group having 1 to 12 carbon atoms, the phenyl group which may have a substituent, or the aralkyl group which may have a substituent are the same as those in the above formula (A-2).
  • the pigment composition can be used by mixing the diketopyrrolopyrrole pigment represented by the formula (1) and the specific hetero diketopyrrolopyrrole pigment A separately. Further, specific hetero diketopyrrolopyrrole pigments A and C. synthesized by a succinic acid diester cosynthesis method. I. A mixture of CI Pigment Red 254 may be further mixed with a diketopyrrolopyrrole pigment represented by the formula (1). In these cases, the pigment may be simply mixed before being dispersed in the pigment carrier, or may be pulverized and mixed by a salt milling process.
  • a diketopyrrolopyrrole pigment represented by the formula (1) a specific heterodiketopyrrolopyrrole pigment A of the formula (A-2), and C.I. I.
  • the mass ratio of Pigment Red 254 can be analyzed using TOF-MASS, FD-MASS, LC-MASS, or NMR.
  • a diketopyrrolopyrrole pigment composition is obtained by stirring at room temperature with di-tert-butyl dicarbonate and 4-dimethylaminopyridine in tetrahydrofuran.
  • analysis using NMR, MASS, LC-MASS or the like may be performed.
  • the above analysis may be performed after the hydrogen of the NH group of the pyrrolopyrrole ring is substituted with an alkyl group using an alkyl halide or the like and converted to a soluble diketopyrrolopyrrole.
  • a pigment derivative can be used in the pigment composition for the purpose of suppressing pigment crystal growth and improving pigment dispersibility.
  • the dye derivative used in the pigment composition include a diketopyrrolopyrrole derivative, a benzoisoindole derivative, an anthraquinone derivative, a dianthraquinone derivative, a thiazine indigo derivative, an azo dye derivative, a quinophthalone derivative, and a quinacridone derivative.
  • Examples of the structure of the dye derivative include, but are not limited to, the dye derivative represented by the following formula (4).
  • P is a diketopyrrolopyrrole residue, a benzoisoindole residue, an anthraquinone residue, a dianthraquinone residue, a thiazine indigo residue, an azo dye residue, a quinophthalone residue, or a quinacridone residue;
  • m is an integer of 1 to 4
  • L is independently —OH; —SO 3 H, —COOH, monovalent to trivalent metal salts or alkylammonium salts of these acidic groups; phthalimidomethyl group which may have a substituent; A group represented by (a), (b), (c), (d), (e), or (f);
  • X is, -SO 2 -, - CO - , - CH 2 -, - CH 2 NHCOCH 2 -, - CH 2 NHSO 2 CH 2 -, or a direct bond
  • Y is —NH—, —O—,
  • R 16 and R 17 may be combined to form a heterocyclic ring which may have a substituent, and further contains a nitrogen, oxygen or sulfur atom, if necessary, R 18 , R 19 , R 20 , R 21 and R 22 are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted carbon.
  • R 23 is a substituent represented by formula (a) or formula (b)
  • R 24 is a chlorine atom, —OH, an alkoxyl group, a substituent represented by the formula (a) or the formula (b)
  • Z is —CONH—, —NHCO—, —SO 2 NH—, or —NHSO 2 —
  • R 25 is a hydrogen atom, —NH 2 , —NHCOCH 3 , —NHR 26 , or a substituent represented by the formula (c), wherein R 26 has 1 to carbon atoms that may have a substituent.
  • Examples of monovalent to trivalent metals include sodium, potassium, magnesium, calcium, iron, and aluminum.
  • Examples of the alkylammonium salt include ammonium salts of long-chain monoalkylamines such as octylamine, laurylamine, and stearylamine, or palmityltrimethylammonium salt, dilauryldimethylammonium salt, and distearyldimethylammonium salt. A quaternary alkyl ammonium salt is mentioned.
  • the alkyl group which may have a substituent As the phthalimidomethyl group which may have a substituent, the alkyl group which may have a substituent, the alkenyl group which may have a substituent, or the heterocyclic substituent which may have a substituent, A halogen atom, a nitro group, a cyano group, a carbamoyl group, an N-substituted carbamoyl group, a sulfamoyl group, an N-substituted sulfamoyl group, an alkoxyl group having 1 to 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, and the like. However, it is not limited to these.
  • the dye derivative is a sulfonation reaction by heating in sulfuric acid or fuming sulfuric acid, a phthalimide methylation reaction in which dehydration condensation is performed with N-hydroxymethylphthalimide in sulfuric acid, and chlorosulfonated using chlorosulfonic acid and thionyl chloride. It is synthesized by a known production method such as sulfonamidation reaction in which an amine component such as dimethylaminopropylamine is reacted.
  • Examples of the amine component used for forming the substituent represented by the above formula (a), formula (b), and formula (c) include dimethylamine, diethylamine, methylethylamine, N, N-ethyl. Isopropylamine, N, N-ethylpropylamine, N, N-methylbutylamine, N, N-methylisobutylamine, N, N-butylethylamine, N, N-tert-butylethylamine, diisopropylamine, dipropylamine, N , N-sec-butylpropylamine, dibutylamine, di-sec-butylamine, diisobutylamine, N, N-isobutyl-sec-butylamine, diamylamine, diisoamylamine, dihexylamine, dicyclohexylamine, di (2-ethylhexyl) ) Amine, dioctylamine, N,
  • the azo dye derivative can be produced by introducing the substituent into a diazo component or a coupling component in advance and then performing a coupling reaction.
  • the method of using the pigment derivative is not limited to the method of mixing in water or an organic solvent during the production of the pigment or the salt.
  • the method of adding at the time of a milling process is mentioned.
  • the method of mixing the pigment derivative in water or an organic solvent at the time of pigment production or the method of adding it at the time of salt milling exhibits the effect of suppressing the crystal growth of the diketopyrrolopyrrole pigment, but the effect of suppressing the crystal growth In order to exhibit the above, it is desired that the dye derivative is efficiently adsorbed on the surface of the diketopyrrolopyrrole pigment and is not easily desorbed.
  • the structure of the pigment derivative is often considered to have a partial chemical structure similar to the pigment used.
  • a dye derivative having a diketopyrrolopyrrole structure, a thiazineindigo structure, a benzoisoindole structure, or a quinacridone structure is generally effective. It is.
  • a dye derivative when using a dye derivative, it is desired that the color tone of the diketopyrrolopyrrole pigment composition is not impaired as much as possible. From the viewpoint of hue, it is preferable to use diketopyrrolopyrrole derivatives, benzoisoindole derivatives, thiazineindigo derivatives, azo dye derivatives, or quinophthalone derivatives that exhibit yellow and orange colors.
  • the amount of the pigment derivative is preferably in the range of 0.5 to 40 parts by mass with respect to 100 parts by mass of the diketopyrrolopyrrole pigment composition. More preferably, it is in the range of 3 to 35 parts by mass with respect to 100 parts by mass of the diketopyrrolopyrrole pigment composition. When the amount is less than 0.5 part by mass, the crystal growth suppressing effect may not be sufficient, and when the amount is more than 40 parts by mass, the good color tone of the diketopyrrolopyrrole pigment may be impaired.
  • diketopyrrolopyrrole derivatives specifically, a compound represented by the following formula (5) or formula (6) can be used, but is not limited thereto.
  • benzoisoindole derivatives As the benzoisoindole derivative, specifically, a compound represented by the following formula (7) can be used, but is not limited thereto.
  • anthraquinone derivative Specifically as an anthraquinone derivative, the compound represented by following formula (8) can be used, However, It is not limited to these.
  • dianthraquinone derivatives specifically, a compound represented by the following formula (9) can be used, but is not limited thereto.
  • thiazine indigo derivatives specifically, a compound represented by the following formula (10) can be used, but is not limited thereto.
  • azo dye derivatives specifically, a compound represented by the following formula (11), formula (12), or formula (13) can be used, but is not limited thereto.
  • quinophthalone derivatives specifically, compounds represented by the following formulas (14-1) to (14-13) can be used, but are not limited thereto.
  • quinacridone derivatives As the quinacridone derivative, specifically, a compound represented by the following formula (15) can be used, but is not limited thereto.
  • the pigment composition of the first embodiment preferably has a very fine primary particle diameter, a narrow distribution width, and a sharp particle size distribution.
  • the average primary particle diameter (volume average particle diameter) determined by TEM (transmission electron microscope) of the pigment composition of the first embodiment is preferably in the range of 5 to 70 nm. If it is smaller than 5 nm, dispersion in an organic solvent may become difficult. On the other hand, if it exceeds 70 nm, a sufficient contrast ratio may not be obtained. For these reasons, a more preferable range is 10 to 40 nm.
  • the average primary particle size is in the above range at the stage of preparing a pigment composition by synthesizing and mixing the pigment, it may be used as it is, but if not, the pigment is refined by salt milling or the like It is desirable to perform sizing.
  • the pigment containing the diketopyrrolopyrrole pigment composition of the first embodiment is preferably used after being refined, and a salt milling process is preferred as the refinement method.
  • Salt milling is a process of heating a mixture of pigment, water-soluble inorganic salt and water-soluble organic solvent using a kneader such as a kneader, trimix, two-roll mill, three-roll mill, ball mill, attritor or sand mill. Then, after mechanically kneading, the water-soluble inorganic salt and the water-soluble organic solvent are removed by washing with water.
  • the water-soluble inorganic salt works as a crushing aid, and it is thought that the pigment is crushed using the high hardness of the inorganic salt during salt milling, thereby generating an active surface and causing crystal growth. Yes. Therefore, the crushing of the pigment and the crystal growth occur simultaneously during the kneading, and the primary particle diameter of the pigment obtained varies depending on the kneading conditions.
  • the heating temperature is preferably 35 to 150 ° C.
  • the kneading time for the salt milling treatment is preferably 2 to 24 hours from the viewpoint of the balance between the particle size distribution of the primary particles of the obtained pigment and the cost required for the salt milling treatment.
  • water-soluble inorganic salt used for the salt milling treatment sodium chloride, barium chloride, potassium chloride, sodium sulfate and the like can be used, but sodium chloride (salt) is preferably used from the viewpoint of price.
  • the water-soluble inorganic salt is preferably used in an amount of 50 to 2000 parts by mass, and most preferably 300 to 1200 parts by mass with respect to 100 parts by mass of the pigment from both the processing efficiency and production efficiency.
  • the water-soluble organic solvent is not particularly limited as long as it functions to wet the pigment and the water-soluble inorganic salt and dissolves (mixes) in water and does not substantially dissolve the inorganic salt to be used.
  • a high boiling point solvent having a boiling point of 120 ° C. or higher is preferable from the viewpoint of safety because the temperature rises during salt milling and the solvent is easily evaporated.
  • the water-soluble organic solvent is preferably used in an amount of 5 to 1000 parts by weight, and most preferably 50 to 500 parts by weight, based on 100 parts by weight of the pigment.
  • a pigment derivative When performing the salt milling treatment, a pigment derivative may be used in combination to improve kneading efficiency, which is very effective for making the pigment finer and sized.
  • a pigment derivative In making the diketopyrrolopyrrole pigment composition fine, it is preferable to use the above-mentioned dye derivative, but the invention is not limited thereto.
  • the amount of the dye derivative used is preferably such that it does not affect the color tone, that is, in the range of 0.5 to 40 parts by mass with respect to 100 parts by mass of the pigment.
  • a resin when performing the salt milling treatment, a resin may be added as necessary.
  • 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 resin used is solid at room temperature, preferably insoluble in water, and more preferably partially soluble in the organic solvent.
  • the amount of the resin used is preferably in the range of 5 to 200 parts by mass with respect to 100 parts by mass of the pigment.
  • a second embodiment is a diketopyrrolopyrrole pigment composition for a color filter, comprising a brominated diketopyrrolopyrrole pigment of the following formula (1) and a specific hetero diketopyrrolopyrrole pigment of the following formula (B-2):
  • C.I. I It has been found that the brightness is improved by applying a brominated diketopyrrolopyrrole pigment (formula (1)) to the color filter instead of Pigment Red 254 (chlorinated diketopyrrolopyrrole pigment). Further, this brominated diketopyrrolopyrrole pigment and a diketopyrrolopyrrole pigment having a substituent introduced asymmetrically (formula (B-2) (hereinafter referred to as “specific hetero diketopyrrolopyrrole pigment B”) are specified. It has been found that by using a pigment composition contained in a ratio, a color filter with high brightness, high contrast, and suppressed crystal precipitation due to a heating process can be obtained.
  • a pigment composition contained in a ratio a color filter with high brightness, high contrast, and suppressed crystal precipitation due to a heating process can be obtained.
  • the second embodiment it is possible to provide a pigment composition for a color filter that has high brightness and high contrast and does not cause crystal precipitation of a diketopyrrolopyrrole pigment even in the heating step.
  • a and B are each independently a hydrogen atom, a fluorine atom, a chlorine atom, an iodine atom, a cyano group, an alkyl group having 1 to 12 carbon atoms, an optionally substituted phenyl group, —CF 3 , — OR 1 , —SR 2 , —N (R 3 ) R 4 , —COOR 5 , —CONH 2 , —CONHR 6 , —CON (R 7 ) R 8 , —SO 2 NH 2 , —SO 2 NHR 9 , or , —SO 2 N (R 10 ) R 11 , R 1 to R 11 are each independently an alkyl group having 1 to 12 carbon atoms, a phenyl group which may have a substituent, or an aralkyl group which may have a substituent.
  • a and B are not hydrogen atoms at the same time.
  • the alkyl group having 1 to 12 carbon atoms may be linear or branched, and specifically includes methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl.
  • Examples of the phenyl group which may have a substituent include an alkyl group having 1 to 4 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. And a phenyl group having a substituent such as a group. The phenyl group may have one or more of these substituents.
  • phenyl group More specifically, 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 thereof include, but are not limited to, a phenyl group.
  • Examples of the aralkyl group which may have a substituent include an alkyl group having 1 to 4 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. And an aralkyl group having a substituent such as a group. The aralkyl group may have one or more of these substituents.
  • benzyl group 4-methylbenzyl group, 4-tert-butylbenzyl group, 4-methoxybenzyl group, 4-nitrobenzyl group, 2,4-dichlorobenzyl group and the like can be mentioned. It is not limited.
  • the formula (B-2) used for the pigment composition the formula (B-2-1), the formula (B-2-2), the formula (B-2-4a), the formula (B-2-6b), Formula (B-2-7) and the like are preferable from the viewpoints of hue, contrast, and crystal precipitation suppression effect.
  • the ratio of the formula (1) and the formula (B-2) in the pigment composition is in the range of 97: 3 to 85:15 by mass ratio.
  • the ratio of the formula (B-2) exceeds 15% by mass, the crystal precipitation suppressing effect can be obtained, but the excellent color tone of the formula (1) is impaired. This is due to the fact that the brominated diketopyrrolopyrrole pigment of the formula (1) is superior in color tone to the specific hetero diketopyrrolopyrrole pigment B of the formula (B-2).
  • the ratio of the formula (B-2) is less than 3% by mass, the effects of increasing the contrast and suppressing crystal precipitation are not sufficient.
  • the crystal precipitation suppressing effect is not sufficient, light scattering occurs due to the crystalline foreign matter deposited on the surface of the coating film in the heating step, causing a decrease in brightness and contrast ratio. Therefore, by using the diketopyrrolopyrrole pigment composition in the above mass ratio range, high brightness and high contrast can be achieved, and crystal precipitation of the diketopyrrolopyrrole pigment can be suppressed even by the heating step.
  • the pigment composition contains a diketopyrrolopyrrole pigment of the formula (1) and a diketopyrrolopyrrole pigment other than the specific heterodiketopyrrolopyrrole pigment B of the formula (B-2) as long as the effect is not impaired. You may use together.
  • the above-mentioned formula (A-2) is specified. It is also possible to use heterodiketopyrrolopyrrole pigments. At this time, the content of the specific heterodiketopyrrolopyrrole pigment represented by the formula (A-2) is preferably 1% by mass to 15% by mass based on the total mass of the diketopyrrolopyrrole pigment.
  • the brominated diketopyrrolopyrrole pigment of the formula (1) can be produced by a method similar to the method in the first embodiment.
  • Specific heterodiketopyrrolopyrrole pigment B of the formula (B-2) is described in, for example, the document Synth. Commun. 1988, 18, 1213 and Tetrahedron, 58 (2002) 5547-5565.
  • the method for producing the specific heterodiketopyrrolopyrrole pigment B is not limited to this method.
  • the brominated diketopyrrolopyrrole pigment of the formula (1) and the specific hetero diketopyrrolopyrrole pigment B of the formula (B-2) can be simultaneously produced as a fine pigment composition.
  • This can be achieved by using a method using at least two structurally different benzonitrile compounds in the succinic acid diester synthesis method (hereinafter referred to as “succinic acid diester co-synthesis method”).
  • succinic acid diester co-synthesis method a method using at least two structurally different benzonitrile compounds in the succinic acid diester synthesis method.
  • succinic acid diester co-synthesis method a method using at least two structurally different benzonitrile compounds in the succinic acid diester synthesis method.
  • a plurality of benzonitrile compounds to be used are selected from 4-bromobenzonitrile and a benzonitrile compound represented by the following formula (B-3).
  • a and B are each independently a hydrogen atom, a fluorine atom, a chlorine atom, an iodine atom, a cyano group, an alkyl group having 1 to 12 carbon atoms, an optionally substituted phenyl group, —CF 3 , — OR 1 , —SR 2 , —N (R 3 ) R 4 , —COOR 5 , —CONH 2 , —CONHR 6 , —CON (R 7 ) R 8 , —SO 2 NH 2 , —SO 2 NHR 9 , or , —SO 2 N (R 10 ) R 11 , R 1 to R 11 are each independently an alkyl group having 1 to 12 carbon atoms, a phenyl group which may have a substituent, or an aralkyl group which may have a substituent.
  • a and B are not hydrogen atoms at the same time.
  • the alkyl group having 1 to 12 carbon atoms, the phenyl group which may have a substituent, or the aralkyl group which may have a substituent are the same as those in the above formula (B-2).
  • the pigment composition may be prepared by separately mixing a brominated diketopyrrolopyrrole pigment and a specific hetero diketopyrrolopyrrole pigment B.
  • the pigment composition is simultaneously prepared by a succinic acid diester cosynthesis method. It is desirable to produce a composition. When using what was manufactured separately, you may mix simply before disperse
  • the mixing ratio (molar ratio) of B-3) is about 80:20 to 98: 2 It becomes the range.
  • a diketopyrrolopyrrole pigment obtained by reacting 2 moles of the benzonitrile compound of the formula (B-3) with 1 mole of the succinic acid diester (that is, diketopyrrolopyrrole containing no bromine atom). Pigment) may be produced, but there is almost no effect because the amount is very small.
  • the reaction ratio of succinic acid diester and benzonitrile compound is basically 2 mol of benzonitrile compound to 1 mol of succinic acid diester, but the amount of succinic acid diester is the amount of benzonitrile compound. If used in excess of about 25 mol%, the yield is effective.
  • the mass ratio of the brominated diketopyrrolopyrrole pigment and the specific hetero diketopyrrolopyrrole pigment B is the same as the mass ratio analysis method in the first embodiment. Can be analyzed.
  • a pigment derivative in the pigment composition of the second embodiment, can be used for the purpose of suppressing pigment crystal growth and improving pigment dispersibility.
  • the dye derivative include the same dye derivatives as the dye derivative of the first embodiment.
  • the preferred amount of the dye derivative used is also the same as in the first embodiment.
  • the diketopyrrolopyrrole pigment composition of the second embodiment preferably has a very fine primary particle diameter, a narrow distribution width, and a sharp particle size distribution.
  • the average primary particle size (number average particle size) determined by TEM (transmission electron microscope) of the diketopyrrolopyrrole pigment composition of the second embodiment is preferably in the range of 5 to 70 nm. If it is smaller than 5 nm, dispersion in an organic solvent may become difficult. On the other hand, if it exceeds 70 nm, a sufficient contrast ratio may not be obtained. For these reasons, a more preferable range is 10 to 40 nm.
  • the average primary particle diameter is in the above range at the stage when the diketopyrrolopyrrole pigment composition is produced by the above synthesis method, it may be used as it is. It is desirable to perform sizing and sizing.
  • the pigment containing the diketopyrrolopyrrole pigment composition of the second embodiment is preferably used after being refined, and a salt milling treatment is preferred as the refinement method.
  • the salt milling process can be performed in the same manner as in the first embodiment.
  • Coloring composition for color filter Next, the coloring composition for color filters which is an embodiment of the present invention will be described.
  • the coloring composition for a color filter according to the third embodiment contains the diketopyrrolopyrrole pigment composition according to the first embodiment.
  • the diketopyrrolopyrrole pigment composition of the first embodiment can be used as a colored composition by being used in combination with a binder resin and an organic solvent. Further, a colorant other than the diketopyrrolopyrrole pigment composition of the first embodiment may be used in combination. For example, the diketopyrrolopyrrole pigment composition of the second embodiment can be used.
  • a pigment or dye other than the diketopyrrolopyrrole pigment composition of the first embodiment is used alone or in a range that does not impair the effect, for example, for adjusting chromaticity. Two or more types may be used in combination.
  • the diketopyrrolopyrrole pigment composition of the first embodiment is 30% by mass to 100% by mass in the total amount of the colorant (100% by mass). A range is preferable. More preferably, it is in the range of 50% by mass to 100% by mass. When the diketopyrrolopyrrole pigment composition of the first embodiment is less than 30% by mass, the effect of excellent brightness may not be sufficiently exhibited.
  • binder resin examples of the binder resin contained in the coloring composition include conventionally known thermoplastic resins and thermosetting resins.
  • the binder resin (CB) containing the alkali-soluble photosensitive resin (C-B1) in the fifth embodiment may be used as the binder resin.
  • the structural unit (Db1) in the sixth embodiment may be used. It is also possible to use a binder resin (DB) containing a resin (DB1) having (Db3).
  • thermoplastic resin examples include acrylic resin, butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, polyurethane resin Polyester resins, vinyl resins, alkyd resins, polystyrene resins, polyamide resins, rubber resins, cyclized rubber resins, celluloses, polyethylene (HDPE, LDPE), polybutadiene, polyimide resins, and the like.
  • a resin having a spectral transmittance of preferably 80% or more, more preferably 95% or more in the entire wavelength region of 400 to 700 nm in the visible light region is preferable.
  • the alkali-soluble vinyl resin which copolymerized the acidic group containing ethylenically unsaturated monomer it is preferable to use the alkali-soluble vinyl resin which copolymerized the acidic group containing ethylenically unsaturated monomer.
  • an energy ray curable resin having an ethylenically unsaturated active double bond can also be used.
  • alkali-soluble vinyl resin obtained by copolymerizing an acidic group-containing ethylenically unsaturated monomer examples include resins having an acidic group such as a carboxyl group or a sulfone group.
  • Specific examples of the alkali-soluble resin include an acrylic resin having an acidic group, an ⁇ -olefin / (anhydrous) maleic acid copolymer, a styrene / styrene sulfonic acid copolymer, an ethylene / (meth) acrylic acid copolymer, or Examples include isobutylene / (anhydrous) maleic acid copolymer.
  • At least one resin selected from an acrylic resin having an acidic group and a styrene / styrene sulfonic acid copolymer, particularly an acrylic resin having an acidic group, is preferably used because of its high heat resistance and transparency.
  • Energy ray curable resins having ethylenically unsaturated active double bonds include reactive substitution of isocyanate groups, aldehyde groups, epoxy groups, etc. on polymers having reactive substituents such as hydroxyl groups, carboxyl groups, amino groups, etc.
  • a resin in which a photo-crosslinkable group such as a (meth) acryloyl group or a styryl group is introduced into the polymer by reacting a (meth) acrylic compound having a group or cinnamic acid is used.
  • polymers containing acid anhydrides such as styrene-maleic anhydride copolymer and ⁇ -olefin-maleic anhydride copolymer are half-esterified with a (meth) acrylic compound having a hydroxyl group such as hydroxyalkyl (meth) acrylate.
  • a modified version is also used.
  • thermoplastic resin having both alkali-soluble performance and energy ray curing performance is also preferable as the photosensitive coloring composition for color filters.
  • Examples of the monomer constituting the thermoplastic resin 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, phenoxyethyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, methoxypol
  • thermosetting resin examples include epoxy resin, benzoguanamine resin, rosin-modified maleic acid resin, rosin-modified fumaric acid resin, melamine resin, urea resin, and phenol resin.
  • an epoxy resin and a melamine resin are used more suitably from a viewpoint of heat resistance improvement.
  • the mass average molecular weight (Mw) of the binder resin is preferably in the range of 5,000 to 80,000, more preferably in the range of 7,000 to 50,000 in order to disperse the colorant preferably.
  • the number average molecular weight (Mn) is preferably in the range of 2,500 to 40,000, and the value of Mw / Mn is preferably 10 or less.
  • the mass average molecular weight (Mw) and the number average molecular weight (Mn) were determined by connecting four separation columns in series in the gel permeation chromatography “HLC-8120GPC” manufactured by Tosoh Corporation.
  • the molecular weight in terms of polystyrene measured using “TSK-GEL SUPER H5000”, “H4000”, “H3000”, and “H2000” manufactured by the company and using tetrahydrofuran as the mobile phase.
  • the binder resin When the binder resin is used as a coloring composition for a color filter, an aliphatic group and an aromatic group which act as an affinity group for a pigment adsorbing group and an alkali-soluble group during development, a pigment carrier and a solvent. It is desirable to consider the balance. From the viewpoint of pigment dispersibility, developability, and durability, it is preferable to use a resin having an acid value of 20 to 300 mgKOH / g. When the acid value is less than 20 mgKOH / g, the solubility in a developing solution is low, and it may be difficult to form a fine pattern. If it exceeds 300 mgKOH / g, a fine pattern may not remain by development.
  • the binder resin can be used in an amount of 20 to 500 parts by mass with respect to 100 parts by mass of the colorant. If the amount is less than 20 parts by mass, the film formability and various resistances may be insufficient. If the amount is more than 500 parts by mass, the pigment concentration may be low and color characteristics may not be exhibited.
  • the coloring agent is sufficiently dispersed and permeated in the coloring agent carrier, and is applied onto a substrate such as a glass substrate so as to have a dry film thickness of 0.2 to 5 ⁇ m to form a filter segment.
  • an organic solvent is included. The organic solvent is selected in consideration of good applicability of the coloring composition, solubility of each component of the coloring composition, and safety.
  • the organic solvent is preferably used in an amount of 500 to 4000 parts by weight with respect to 100 parts by weight of the colorant, because the colored composition can be adjusted to an appropriate viscosity and a filter segment having a desired uniform film thickness can be formed. .
  • the coloring composition comprises the above-mentioned diketopyrrolopyrrole pigment composition in a kneader carrier comprising the binder resin and an organic solvent, a kneader, a two-roll mill, a three-roll mill, a ball mill, a horizontal sand mill, and a vertical sand mill. It can be produced by finely dispersing using various dispersing means such as an annular type bead mill or an attritor. Moreover, the coloring composition may disperse the diketopyrrolopyrrole pigment composition and other coloring agents simultaneously in the coloring agent carrier, or may mix them separately in the coloring material carrier.
  • a dispersion aid such as a pigment derivative, a resin-type dispersant, or a surfactant may be appropriately contained. Since the dispersion aid has a great effect of preventing re-aggregation of the colorant after dispersion, the color composition obtained by dispersing the colorant in the colorant carrier using the dispersion aid has contrast and viscosity stability. Become good.
  • the amount is preferably 0.1 to 55 parts by mass, more preferably 0.1 to 45 parts by mass with respect to 100 parts by mass of the colorant.
  • the blending amount of the resin-type dispersant and the surfactant is less than 0.1 part by mass, it is difficult to obtain the added effect. May have an effect.
  • the coloring composition may further contain, for example, the following components in addition to the dispersion aid as an optional component. Specific examples of the optional component are as described below.
  • the coloring composition can be used as a photosensitive coloring composition by further adding a photopolymerizable monomer and / or a photopolymerization initiator.
  • the photopolymerizable monomer used in the photosensitive coloring composition includes a monomer or an oligomer that is cured by ultraviolet rays or heat to generate a transparent resin. These may be used alone or in combination of two or more. Can be used.
  • the blending amount of the monomer is preferably 5 to 400 parts by mass with respect to 100 parts by mass of the colorant, and more preferably 10 to 300 parts by mass from the viewpoint of photocurability and developability.
  • a photopolymerization initiator is added in the form of a solvent development type or alkali development type colored resist material.
  • the photopolymerization initiator is preferably 2 to 200 parts by mass with respect to 100 parts by mass of the colorant in the photosensitive coloring composition, and 3 to 150 parts by mass from the viewpoint of photocurability and developability. More preferred.
  • the photosensitive coloring composition can contain a sensitizer.
  • the blending amount when using the sensitizer is preferably 3 to 60 parts by mass with respect to 100 parts by mass of the photopolymerization initiator contained in the photosensitive coloring composition. From the viewpoint of photocurability and developability. From 5 to 50 parts by mass is more preferable.
  • the photosensitive coloring composition can contain a polyfunctional thiol that functions as a chain transfer agent.
  • the polyfunctional thiol is preferably a compound having two or more thiol groups.
  • the content of the polyfunctional thiol is preferably 0.1 to 30% by mass, more preferably 1 to 20% by mass, based on the mass (100% by mass) of the total solid content of the photosensitive coloring composition. If the content of the polyfunctional thiol is less than 0.1% by mass, the effect of adding the polyfunctional thiol may not be sufficiently obtained. If the content exceeds 30% by mass, the sensitivity may be too high and the resolution may decrease. .
  • the coloring composition can contain an antioxidant.
  • the antioxidant increases the transmittance of the coating film in order to prevent the photopolymerization initiator and thermosetting compound contained in the colored composition from being oxidized and yellowing due to a thermal process during thermal curing or ITO annealing. be able to. Therefore, by including an antioxidant, yellowing due to oxidation during the heating step can be prevented, and high coating film transmittance can be obtained.
  • the content of the antioxidant is more preferably 0.5 to 5.0% by mass on the basis of the solid content mass of the coloring composition (100% by mass) because the brightness and sensitivity are good.
  • the coloring composition can contain an amine compound that functions to reduce dissolved oxygen.
  • Leveling agent In order to improve the leveling property of the composition on the transparent substrate, it is preferable to add a leveling agent to the coloring composition.
  • the leveling agent content is preferably 0.003 to 0.5% by mass based on the total mass of the coloring composition (100% by mass).
  • the coloring composition may contain a curing agent, a curing accelerator, and the like as necessary.
  • the content of the curing accelerator is preferably 0.01 to 15 parts by mass with respect to 100 parts by mass of the thermosetting resin.
  • the coloring composition can contain a storage stabilizer in order to stabilize the viscosity with time. Moreover, in order to improve adhesiveness with a transparent substrate, adhesion improving agents, such as a silane coupling agent, can also be contained.
  • the storage stabilizer can be used in an amount of 0.1 to 10% by mass based on the total amount of the colorant (100% by mass).
  • the adhesion improver can be used in an amount of 0.01 to 10% by mass, preferably 0.05 to 5% by mass, based on the total amount of the colorant in the coloring composition (100% by mass).
  • the coloring composition is obtained by means of centrifugation, filtration with a sintered filter or a membrane filter, etc., coarse particles of 5 ⁇ m or more, preferably coarse particles of 1 ⁇ m or more, more preferably coarse particles of 0.5 ⁇ m or more and mixed dust Is preferably removed.
  • a coloring composition does not contain a particle
  • the coloring composition for a color filter of the fourth embodiment contains the diketopyrrolopyrrole pigment composition of the second embodiment.
  • the diketopyrrolopyrrole pigment composition of the second embodiment can be used as a colored composition when used in combination with a binder resin and an organic solvent. Further, a colorant other than the diketopyrrolopyrrole pigment composition of the second embodiment may be used in combination. For example, the diketopyrrolopyrrole pigment composition of the first embodiment can be used.
  • the coloring composition is a pigment or dye other than the diketopyrrolopyrrole pigment composition of the second embodiment as long as the effect is not impaired. Also good.
  • the diketopyrrolopyrrole pigment composition of the second embodiment is 40% by mass to 100% by mass in the total amount of the colorant (100% by mass). A range is preferable. More preferably, it is in the range of 60% by mass to 100% by mass. When the diketopyrrolopyrrole pigment composition of the second embodiment is 40% by mass or less, the effect of excellent brightness and contrast ratio may not be exhibited sufficiently.
  • binder resin examples of the binder resin contained in the coloring composition include conventionally known thermoplastic resins and thermosetting resins. Examples of the binder resin include the same binder resin as the binder resin in the third embodiment. The preferred amount of binder resin used is also the same as in the third embodiment.
  • the coloring agent is sufficiently dispersed and permeated in the coloring agent carrier, and is applied onto a substrate such as a glass substrate so as to have a dry film thickness of 0.2 to 5 ⁇ m to form a filter segment.
  • an organic solvent is included.
  • the organic solvent can be selected in the same manner as the selection method in the third embodiment.
  • the preferred amount of organic solvent used is also the same as in the third embodiment.
  • the colored composition of the fourth embodiment can be produced by the same production method as the colored composition of the third embodiment.
  • the coloring composition of the fourth embodiment includes a dispersion aid, a photopolymerizable monomer and / or a photopolymerization initiator, a sensitizer, a polyfunctional thiol, an antioxidant, an amine compound, a leveling agent, and a curing agent.
  • Optional components such as an agent, a curing accelerator, and other additives can be contained. Specific examples of these optional components are the same as in the third embodiment. Further, preferred examples, preferred use amounts, and the like are the same as in the third embodiment.
  • the colored composition of the fourth embodiment preferably removes coarse particles in the same manner as the colored composition of the third embodiment.
  • the coloring composition for a color filter according to the fifth embodiment includes a pigment (A), a binder resin (CB), and a solvent, and the pigment (A) is a pigment (A1) represented by the formula (1). And the binder resin (CB) contains an alkali-soluble photosensitive resin (C-B1).
  • the color filter coloring composition of the fifth embodiment can be used as a photosensitive coloring composition.
  • C.I. I By using a coloring composition containing a brominated diketopyrrolopyrrole pigment (formula (1)) and an alkali-soluble photosensitive resin instead of Pigment Red 254 (chlorinated diketopyrrolopyrrole pigment), high brightness, high It has been found that a color filter having a high-definition filter segment with a contrast ratio and suppressed crystal precipitation due to the heating process can be obtained.
  • the filter has a high brightness and a high contrast ratio and does not cause crystal precipitation of the diketopyrrolopyrrole pigment by the heating process, but also has good filter segments such as sensitivity and linearity.
  • the coloring composition for color filters which is excellent in the balance of performance required when forming can be provided.
  • the pigment (A) includes the pigment (A1) represented by the formula (1). ⁇ Pigment (A1) >>
  • the brominated diketopyrrolopyrrole pigment which is the pigment (A1) represented by the formula (1), can be produced by a method similar to the method in the first embodiment.
  • the pigment (A1) represented by the formula (1) it is possible to obtain a red coloring composition having higher brightness and higher contrast ratio than before.
  • the pigment (A) it is possible to use the diketopyrrolopyrrole pigment composition in the first embodiment or the diketopyrrolopyrrole pigment composition in the second embodiment.
  • the coloring composition may be used in combination with a pigment other than the pigment (A1), and as such a pigment, an organic or inorganic pigment may be used alone or in combination of two or more.
  • a pigment other than the pigment (A1) an organic or inorganic pigment may be used alone or in combination of two or more.
  • organic pigments pigments having high color developability and high heat resistance are preferable, and organic pigments are usually used.
  • organic pigments examples include diketopyrrolopyrrole pigments other than pigment (A1); azo pigments such as azo, disazo, polyazo; phthalocyanine types such as copper phthalocyanine, halogenated copper phthalocyanine, and metal-free phthalocyanine
  • Anthraquinone pigments such as aminoanthraquinone, diaminodianthraquinone, anthrapyrimidine, flavantron, anthanthrone, indanthrone, pyrantrone, violanthrone; quinacridone pigments; dioxazine pigments; perinone pigments; perylene pigments; thiaindigo pigments; Examples thereof include isoindoline pigments; isoindolinone pigments; quinophthalone pigments; selenium pigments; metal complex pigments.
  • pigments from the group consisting of diketopyrrolopyrrole pigments other than pigment (A1), azo pigments, anthraquinone pigments, perylene pigments, quinacridone pigments, benzimidazolone pigments, and quinoline pigments. It is preferable to include at least one or more selected. Like the pigment (A1), these are red pigments, which facilitate color adjustment by adjusting the blending ratio, and are preferable because they are excellent in light resistance and heat resistance.
  • Inorganic pigments include barium sulfate, zinc white, lead sulfate, yellow lead, zinc yellow, red bean (red iron (III) oxide), cadmium red, ultramarine, bitumen, chromium oxide green, cobalt green, amber, titanium black.
  • examples thereof include metal oxide powders such as synthetic iron black, titanium oxide, and iron tetroxide, metal sulfide powders, and metal powders.
  • Inorganic pigments are used in combination with organic pigments in order to ensure good coatability, sensitivity, developability and the like while maintaining a balance between saturation and lightness.
  • the content of the pigment (A1) represented by the formula (1) is 40 to 100% by weight, preferably 50 to 100% by weight, out of the total 100% by weight of the pigment (A). More preferably, it is 60 to 100% by weight. This content range is preferable in that the color characteristics of the pigment (A1) represented by the formula (1) can be sufficiently expressed.
  • the content of the pigment (A) component is preferably 10% by weight or more, more preferably 15% by weight or more from the viewpoint of obtaining sufficient color reproducibility in 100% by weight of the total nonvolatile components of the coloring composition, Preferably it is 20 weight% or more. Further, since the stability of the coloring composition is improved, the content of the preferred pigment (A) component is 90% by weight or less, more preferably 80% by weight or less, and most preferably 70% by weight or less. is there.
  • the photosensitive coloring composition may further contain a dye for the purpose of color matching within a range that does not decrease the heat resistance.
  • the pigment (A1) and other pigments are preferably used after being refined.
  • the primary particle size of the refined pigment is preferably 20 nm or more because of good dispersion in the colorant carrier. Moreover, since it can form a filter segment with high contrast ratio, it is preferable that it is 100 nm or less. A particularly preferred range is from 25 to 85 nm.
  • the primary particle diameter of the pigment can be measured by directly measuring the size of the primary particle from an electron micrograph of the pigment using a TEM (transmission electron microscope). Specifically, the minor axis diameter and major axis diameter of the primary particles of each pigment are measured, and the average is taken as the particle diameter of the pigment particles. Next, for 100 or more pigment particles, the volume of each particle is approximated to a cube having the obtained particle diameter to obtain an average volume, and the length of one side of the cube having this average volume is determined as the average primary The particle size.
  • TEM transmission electron microscope
  • the specific surface area of these finely divided pigments by the BET method is preferably 60 m 2 / g to 130 m 2 / g.
  • the specific surface area of the pigment (A) is smaller than the lower limit value, the luminance and contrast ratio of the color filter may be lowered.
  • the specific surface area is larger than the upper limit, it may be difficult to disperse the pigment, and it may be difficult to maintain the stability as the coloring composition and ensure the fluidity. As a result, the luminance and contrast ratio characteristics of the color filter tend to deteriorate.
  • a method of controlling the specific surface area of the pigment As a means for controlling the specific surface area of the pigment, a method of controlling the specific surface area by mechanically pulverizing the pigment (referred to as a grinding method), a solution dissolved in a good solvent is introduced into a poor solvent, and a desired specific surface area of the pigment is controlled.
  • a method of precipitating a pigment referred to as a precipitation method
  • a method of producing a pigment having a desired specific surface area at the time of synthesis referred to as a synthetic precipitation method
  • an appropriate method can be selected for each pigment. Any of the above methods may be used as a method for controlling the specific surface area of the pigment contained in the coloring composition.
  • the pigment used in the fifth embodiment is preferably refined by a salt milling process among the grinding methods, and a filter segment having a higher contrast ratio can be formed by using such a pigment.
  • the salt milling treatment can be performed in the same manner as in the diketopyrrolopyrrole pigment composition.
  • Binder resin (CB) The binder resin (CB) disperses the pigment (A) and contains an alkali-soluble photosensitive resin (C-B1).
  • Alkali-soluble photosensitive resin (C-B1) Examples of the alkali-soluble photosensitive resin (C-B1) include resins having an ethylenically unsaturated double bond introduced by the following methods (Ci) and (C-ii).
  • Examples of the method (Ci) include a side chain epoxy of a copolymer obtained by copolymerizing an ethylenically unsaturated monomer having an epoxy group and one or more other monomers. Then, the carboxyl group of the unsaturated monobasic acid having an ethylenically unsaturated double bond is added to the group, and the resulting hydroxyl group is reacted with a polybasic acid anhydride to introduce an ethylenically unsaturated double bond. There is a method of introducing a carboxyl group having the function of a photosensitive resin and having an alkali-soluble function.
  • Examples of the ethylenically unsaturated monomer having an epoxy group include glycidyl (meth) acrylate, methyl glycidyl (meth) acrylate, 2-glycidoxyethyl (meth) acrylate, and 3,4-epoxybutyl (meth) acrylate. And 3,4-epoxycyclohexyl (meth) acrylate, and these may be used alone or in combination of two or more. From the viewpoint of reactivity with the unsaturated monobasic acid in the next step, glycidyl (meth) acrylate is preferred.
  • unsaturated monobasic acids include (meth) acrylic acid, crotonic acid, o-, m-, p-vinylbenzoic acid, ⁇ -haloalkyl of (meth) acrylic acid, alkoxyl, halogen, nitro, cyano-substituted products, etc.
  • Monocarboxylic acid etc. are mentioned, These may be used independently or may use 2 or more types together.
  • polybasic acid anhydrides examples include tetrahydrophthalic anhydride, phthalic anhydride, hexahydrophthalic anhydride, succinic anhydride, maleic anhydride, and the like. These may be used alone or in combination of two or more. It doesn't matter. If necessary, use a tricarboxylic anhydride such as trimellitic anhydride or a tetracarboxylic dianhydride such as pyromellitic dianhydride to increase the number of carboxyl groups. The group can be hydrolyzed.
  • the ethylenically unsaturated double bond can be further increased.
  • a copolymer obtained by copolymerizing an ethylenically unsaturated monomer having a carboxyl group and one or more other monomers is used.
  • an ethylenically unsaturated monomer having an epoxy group is added to a part of the side chain carboxyl group to introduce an ethylenically unsaturated double bond and a carboxyl group.
  • Method (C-ii)> As the method (C-ii), an ethylenically unsaturated monomer having a hydroxyl group is used, and an unsaturated monobasic acid monomer having another carboxyl group or another monomer is copolymerized. There is a method in which the isocyanate group of an ethylenically unsaturated monomer having an isocyanate group is reacted with the side chain hydroxyl group of the copolymer obtained.
  • Examples of the ethylenically unsaturated monomer having a hydroxyl group include 2-hydroxyethyl (meth) acrylate, 2- or 3-hydroxypropyl (meth) acrylate, 2- or 3- or 4-hydroxybutyl (meth) acrylate, glycerol
  • Examples thereof include hydroxyalkyl (meth) acrylates such as (meth) acrylate or cyclohexanedimethanol mono (meth) acrylate, and these may be used alone or in combination of two or more.
  • polyether mono (meth) acrylate obtained by addition polymerization of ethylene oxide, propylene oxide, and / or butylene oxide to the above hydroxyalkyl (meth) acrylate, (poly) ⁇ -valerolactone, (poly) ⁇ -caprolactone And / or (poly) ester mono (meth) acrylate added with (poly) 12-hydroxystearic acid or the like can also be used.
  • 2-hydroxyethyl (meth) acrylate or glycerol (meth) acrylate is preferred.
  • Examples of the ethylenically unsaturated monomer having an isocyanate group include 2- (meth) acryloyloxyethyl isocyanate, 1,1-bis [(meth) acryloyloxy] ethyl isocyanate, and the like. In addition, two or more types can be used in combination.
  • alkali-soluble photosensitive resin (C-B1) examples include unsaturated monocarboxylic acids such as (meth) acrylic acid, crotonic acid, or ⁇ -chloroacrylic acid, or unsaturated dicarboxylic acids such as maleic acid or fumaric acid. And a resin obtained by using a monomer having a carboxyl group and having an ethylenically unsaturated double bond.
  • ethylenically unsaturated monomers that are precursors of the alkali-soluble photosensitive resin (C-B1) include methyl (meth) methacrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl ( (Meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, s-butyl (meth) acrylate, t-butyl (meth) acrylate, pentyl (meth) acrylate, isopentyl acrylate, neopentyl (meth) acrylate, t- Pentyl (meth) acrylate, 1-methylbutyl (meth) acrylate, hexyl (meth) acrylate, hepta (meth) acrylate, octyl (meth) acrylate, 2-ethylhexyl (meth) acryl
  • the weight average molecular weight (Mw) of the alkali-soluble photosensitive resin (C-B1) is preferably in the range of 5,000 to 100,000, more preferably in the range of 5,000 to 80,000, still more preferably It is in the range of 5,000 to 30,000.
  • the number average molecular weight (Mn) is preferably in the range of 5,000 to 50,000, and the value of Mw / Mn is preferably 10 or less.
  • the weight average molecular weight (Mw) of the alkali-soluble photosensitive resin (C-B1) exceeds 100,000, the interaction between the resins becomes strong and the viscosity of the coloring composition for the color filter becomes high, which makes handling difficult. May be. Further, when the weight average molecular weight (Mw) is less than 5,000, developability and adhesion to a substrate such as glass may be deteriorated.
  • the acid value of the alkali-soluble photosensitive resin (C-B1) is preferably an acid value of 20 to 300 KOH-mg / g from the viewpoints of dispersibility, penetrability, developability and resistance of the pigment.
  • the acid value is less than 20 KOH-mg / g, the solubility in a developing solution is low, and it may be difficult to form a fine pattern. If it exceeds 300 KOH-mg / g, a fine pattern may not remain.
  • the content of the alkali-soluble photosensitive resin (CB1) is preferably 10 to 100% by weight, more preferably 20 to 100% by weight, more preferably 40%, out of the total 100% by weight of the binder resin (CB). ⁇ 100% by weight. If the content of the alkali-soluble photosensitive resin (C-B1) in the binder resin (CB) is 10% by weight or more, the effects of high brightness and high contrast ratio of the colored composition can be easily obtained. It is preferable.
  • the binder resin (CB) can also contain other resins other than the alkali-soluble photosensitive resin (C-B1).
  • the other resin is preferably a resin having a transmittance of preferably 80% or more, more preferably 95% or more in the entire wavelength region of 400 to 700 nm in the visible light region.
  • a thermoplastic resin and a thermosetting resin there are a thermoplastic resin and a thermosetting resin, and these can be used alone or in combination of two or more.
  • thermoplastic resin examples include butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, polyurethane resin, and polyester resin. , Acrylic resins, alkyd resins, polystyrene, polyamide resins, rubber resins, cyclized rubber resins, celluloses, polyethylene, polybutadiene, polyimide resins, and the like.
  • thermosetting resin examples include epoxy resins, benzoguanamine resins, rosin-modified maleic acid resins, rosin-modified fumaric acid resins, melamine resins, urea resins, and phenol resins.
  • thermosetting resin examples include benzoguanamine resin, rosin-modified maleic acid resin, rosin-modified fumaric acid resin, melamine resin, urea resin, and phenol resin.
  • an alkali-soluble resin obtained by copolymerizing an acidic group-containing ethylenically unsaturated monomer can be used in combination.
  • alkali-soluble resins include resins having acidic groups such as carboxyl groups and sulfone groups.
  • Specific examples of the alkali-soluble resin include an acrylic resin having an acidic group, an ⁇ -olefin / (anhydrous) maleic acid copolymer, a styrene / styrene sulfonic acid copolymer, an ethylene / (meth) acrylic acid copolymer, or Examples include isobutylene / (anhydrous) maleic acid copolymer.
  • At least one resin selected from an acrylic resin having an acidic group and a styrene / styrene sulfonic acid copolymer, particularly an acrylic resin having an acidic group, is preferably used because of its high heat resistance and transparency.
  • the binder resin (CB) can be used in an amount of 20 to 400 parts by weight, preferably 50 to 250 parts by weight with respect to 100 parts by weight of the pigment (A) in the coloring composition.
  • the solvent is a filter in which the pigment (A) is sufficiently dispersed in the binder resin (CB), and the colored composition is applied on a substrate such as a glass substrate so that the dry film thickness is 0.2 to 5 ⁇ m. Used to facilitate the formation of segments.
  • the solvent an organic solvent is preferable.
  • the solvent is used in an amount of 800 to 4000 parts by weight with respect to 100 parts by weight of the pigment (A). It is preferable because it can be formed.
  • the photosensitive coloring composition comprises a three-roll mill, a two-roll mill, a sand mill, a kneader, an atom, and a pigment (A) in a dye carrier such as a binder resin (CB) and a solvent, preferably together with a pigment dispersant.
  • a pigment dispersion is produced by finely dispersing using various dispersing means such as a lighter.
  • the pigment dispersion contains a photopolymerization initiator (CD), a binder resin (CB), a photopolymerizable compound, Can be produced by mixing and stirring the sensitizer (CE), polyfunctional thiol, ultraviolet absorber, polymerization inhibitor, storage stabilizer, and other components.
  • a coloring composition containing two or more pigments is prepared by mixing each pigment dispersion separately in a dye carrier and / or solvent, and further mixing a photopolymerization initiator (CD) or light.
  • CD photopolymerization initiator
  • a polymerizable compound or the like can be produced by mixing and stirring.
  • Pigment dispersant (CC) When the pigment (A) is dispersed in the binder resin (CB) and / or solvent, it appropriately contains a pigment dispersant (CC) such as a resin-type pigment dispersant, a dye derivative, and a surfactant. Can be made.
  • the pigment dispersant (CC) is excellent in pigment dispersion and has a great effect of preventing re-aggregation of the pigment after dispersion. Therefore, the pigment dispersant (CC) is used to bind the pigment to the binder resin (CB). ) And / or when a colored composition dispersed in a solvent is used, a color filter having excellent transparency can be obtained.
  • the coloring composition contains an acidic resin type pigment dispersant, particularly from the viewpoint of the stability of the coloring composition. Furthermore, by using an acidic resin-type pigment dispersant and a basic dye derivative in combination, not only the fluidity and stability of the colored composition, but also a filter segment with excellent brightness and high contrast ratio can be obtained. It is preferable.
  • the pigment dispersant (CC) can be used in an amount of 0.1 to 40 parts by weight, preferably 0.1 to 30 parts by weight with respect to 100 parts by weight of the pigment (A).
  • the dye derivative examples include a compound obtained by introducing a basic substituent, an acidic substituent, or a phthalimidomethyl group which may have a substituent into an organic pigment, anthraquinone, acridone, or triazine.
  • the structure is, for example, a compound represented by the following formula (50), and among them, a pigment derivative is preferable.
  • P-Lm formula (50) [In the formula (50), P: organic pigment residue, anthraquinone residue, acridone residue or triazine residue L: basic substituent, acidic substituent, or optionally substituted phthalimidomethyl group m: an integer of 1 to 4 is there]
  • Examples of the dye derivative are described in JP-A-63-305173, JP-B-57-15620, JP-B-59-40172, JP-B-63-17102, or JP-B-5-9469. What is currently used can be used, These can be used individually or in mixture of 2 or more types.
  • examples of the organic pigment constituting the organic pigment residue of P include the following.
  • examples of the organic pigment constituting the organic pigment residue of P include, for example, diketopyrrolopyrrole pigments; azo pigments such as azo, disazo and polyazo; copper phthalocyanine, halogenated copper phthalocyanine, zinc phthalocyanine, halogenated zinc phthalocyanine, Phthalocyanine pigments such as metal-free phthalocyanine; Anthraquinone pigments such as aminoanthraquinone, diaminodianthraquinone, anthrapyrimidine, flavantron, anthanthrone, indanthrone, pyranthrone, violanthrone; quinacridone pigment; dioxazine pigment; perinone pigment; Thioindigo pigments; isoindoline pigments; isoindolinone pigments; selenium pigments; quinophthalone pigments; dioxazine
  • a dye derivative having a basic substituent in which L in the formula (50) is a basic substituent
  • L in the formula (50) is a basic substituent
  • a dye derivative having a basic substituent By including a dye derivative having a basic substituent, a pigment composition having excellent dispersibility, fluidity, and storage stability can be obtained even in the case of a pigment that is difficult to disperse without a dye derivative having a basic substituent. This is preferable.
  • the pigment can be effectively dispersed by the synergistic effect of the acidic resin type dispersant and the dye derivative having a basic substituent, and a pigment composition having excellent fluidity and storage stability can be obtained.
  • L is preferably a substituent selected from the group represented by formulas (51), (52), and (53).
  • X is, -SO 2 -, - CO - , - CH 2 -, - CH 2 NHCOCH 2 -, - CH 2 NHSO 2 CH 2 -, or a direct bond
  • Y is —NH—, —O—, or a direct bond
  • k is an integer from 1 to 10
  • Y 1 is —NH—, —NR 58 —Z—NR 59 —, or a direct bond
  • R 58 and R 59 are each independently a hydrogen bond, an alkyl group having 1 to 36 carbon atoms which may have a substituent, an alkenyl group having 2 to 36 carbon atoms which may have a substituent, or A phenyl group which may have a substituent
  • Z is an alkylene group which may have a substituent, or an arylene group which may have
  • R 56 is a hydrogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, an optionally substituted alkenyl group having 2 to 20 carbon atoms
  • R 57 is a substituent represented by the above formula (51) or a substituent represented by the above formula (52)
  • Q is a hydroxyl group, an alkoxyl group, a substituent represented by the above formula (51), or a substituent represented by the above formula (52).
  • Examples of the amine component used for forming the substituents represented by the formulas (51) to (53) include the same amine component as the amine component in the first embodiment.
  • a dye derivative having a basic substituent can be synthesized by various synthetic routes. For example, after introducing a substituent represented by formulas (54) to (57) into an organic pigment, the amine component reacts with the substituent to form a substituent represented by formulas (51) to (53), For example, N, N-dimethylaminopropylamine, N-methylpiperazine, diethylamine, or 4- [4-hydroxy-6- [3- (dibutylamino) propylamino] -1,3,5-triazin-2-ylamino It can be obtained by reacting aniline or the like.
  • the substituents of formulas (54) to (56) are hydrolyzed and chlorine is substituted with a hydroxyl group. It may be.
  • the formula (54) and the formula (55) are a sulfonic acid group and a carboxylic acid group, respectively, but any of them may be a free acid, or a monovalent to trivalent metal or the above monoamine. Or a salt thereof.
  • the organic pigment is an azo pigment
  • the substituent represented by the formulas (51) to (53) is introduced into the diazo component or the coupling component in advance, and then a coupling reaction is performed, thereby performing the azo pigment derivative.
  • Triazine derivatives having a basic substituent can be synthesized by various synthetic routes.
  • an amine component starting from cyanuric chloride and forming a substituent represented by formulas (51) to (53) on at least one chlorine of cyanuric chloride, such as N, N-dimethylaminopropylamine or N-methyl It is obtained by reacting piperazine or the like and then reacting the remaining chlorine of cyanuric chloride with various amines or alcohols.
  • the colored composition of the fifth embodiment may further contain, for example, the following components in addition to the pigment dispersant as an optional component. Specific examples of the optional component are as described below.
  • photopolymerization initiator (CD) In the photosensitive coloring composition, an alkali development type photosensitive coloring composition is added by adding a photopolymerization initiator (CD) in order to cure the composition by ultraviolet irradiation and form a filter segment by a photolithography method. It can be prepared in the form of
  • the content of the photopolymerization initiator (CD) is preferably 5 to 200 parts by weight with respect to 100 parts by weight of the pigment (A), and 10 to 150 parts by weight from the viewpoint of photocurability and developability. More preferably.
  • the photosensitive coloring composition can contain a sensitizer.
  • the content of the sensitizer is preferably 3 to 60 parts by weight with respect to 100 parts by weight of the photopolymerization initiator (CD) contained in the photosensitive coloring composition, and is photocurable and developable. From the viewpoint, it is more preferably 5 to 50 parts by weight.
  • the photosensitive coloring composition can contain a photopolymerizable compound.
  • the photopolymerizable compound includes a monomer or an oligomer that is cured by ultraviolet rays or heat to generate a resin.
  • the content of the photopolymerizable monomer (CC) is preferably 10 to 300 parts by weight with respect to 100 parts by weight of the pigment (A), and 10 to 200 parts by weight from the viewpoint of photocurability and developability. More preferably, it is a part.
  • the photosensitive coloring composition can contain a polyfunctional thiol (C—F).
  • a polyfunctional thiol is a compound having two or more thiol (SH) groups.
  • CD photopolymerization initiator
  • a thiyl radical that acts as a chain transfer agent and is less susceptible to polymerization inhibition by oxygen is generated in the radical polymerization process after light irradiation.
  • the photosensitive coloring composition obtained has high sensitivity.
  • a polyfunctional aliphatic thiol in which an SH group is bonded to an aliphatic group such as methylene or ethylene group is preferable.
  • the content of the polyfunctional thiol is preferably 0.05 to 100 parts by weight, more preferably 1.0 to 50.0 parts by weight with respect to 100 parts by weight of the pigment (A).
  • the content of the polyfunctional thiol is preferably 0.05 to 100 parts by weight, more preferably 1.0 to 50.0 parts by weight with respect to 100 parts by weight of the pigment (A).
  • polyfunctional thiol By using 0.05 part by weight or more of polyfunctional thiol, better development resistance can be obtained.
  • a monofunctional thiol having one thiol (SH) group is used, such an improvement in development resistance cannot be obtained.
  • the photosensitive coloring composition can contain an ultraviolet absorber. By containing the ultraviolet absorber, the shape and resolution of the pattern can be controlled.
  • the ultraviolet absorber can be used in an amount of 0.01 to 20 parts by weight, preferably 0.05 to 10 parts by weight with respect to 100 parts by weight of the pigment (A). By using 0.01 part by weight or more of the ultraviolet absorber, better resolution can be obtained.
  • the photosensitive coloring composition can contain a polymerization inhibitor. By containing a polymerization inhibitor, the shape and resolution of the pattern can be controlled.
  • the content of the polymerization inhibitor can be used in an amount of 0.01 to 20 parts by weight, preferably 0.05 to 10 parts by weight with respect to 100 parts by weight of the pigment (A). Better resolution can be obtained by using 0.01 parts by weight or more of the polymerization inhibitor.
  • the photosensitive coloring composition can contain a storage stabilizer. By containing a storage stabilizer, the viscosity with time of the composition can be stabilized.
  • the storage stabilizer can be used in an amount of 0.01 to 20 parts by weight, preferably 0.05 to 10 parts by weight with respect to 100 parts by weight of the pigment (A). By using 0.01 part by weight or more of the storage stabilizer, the temporal stability of the coloring composition is improved.
  • the photosensitive coloring composition may contain an adhesion improver such as a silane coupling agent or an amine compound that functions to reduce dissolved oxygen in order to improve the adhesion to the transparent substrate.
  • 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 with respect to 100 parts by weight of the pigment (A).
  • the colored composition of the fifth embodiment preferably removes coarse particles in the same manner as the colored composition of the third embodiment.
  • the coloring composition for a color filter of the sixth embodiment is a coloring composition for a color filter containing a pigment (A), a binder resin (DB), and a solvent, and the pigment (A) is represented by the formula
  • the pigment (A1) shown in (1) is included, and the binder resin (DB) contains a resin (DB1) having the following structural units (Db1) to (Db3).
  • the coloring composition for color filters of the sixth embodiment can be used as a photosensitive coloring composition.
  • C.I. I By using a coloring composition containing a brominated diketopyrrolopyrrole pigment and a binder resin having a specific structure instead of Pigment Red 254 (chlorinated diketopyrrolopyrrole pigment), high brightness, high contrast, and heating process It has been found that a color filter having a high-definition filter segment in which crystal precipitation is suppressed can be obtained.
  • the sixth embodiment when it is used as a photosensitive coloring composition, it has a high brightness and a high contrast ratio and does not cause crystal precipitation of the diketopyrrolopyrrole pigment by the heating process.
  • the pigment (A) is the same pigment as the pigment (A) in the fifth embodiment, and can be obtained by the same method as the production method in the fifth embodiment.
  • the coloring composition of the sixth embodiment may be used in combination with other pigments together with the pigment (A1), and the pigment (A1) and other pigments may It is preferable to use it after miniaturization.
  • the binder resin (DB) contained in the color filter coloring composition contains a resin (DB1) having the following structural units (Db1) to (Db3).
  • R represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms which may have a benzene ring.
  • the broken line in formula (D-3) represents a cyclic structure containing one or more saturated or unsaturated heterocycles which may have a substituent, adjacent to the benzene ring. ]
  • each structural unit is the weight% of the precursor that provides each structural unit to the resin (Db1).
  • the structural unit (Db1) has a carboxyl group and functions as an alkali-soluble site during development. Based on the weight of all the structural units of the binder resin (D-B1), the structural unit (D-b1) is 2 to 60% by weight from the viewpoints of developability and dispersion stability. If it is less than 2% by weight, the removability of the unexposed part by the alkaline developer becomes insufficient, and the dispersion stability is deteriorated. On the other hand, if it exceeds 60% by weight, the dissolution rate in the alkali developer is increased, and the exposed portion is dissolved.
  • Examples of the precursor of the structural unit (Db1) having a carboxyl group include unsaturated monocarboxylic acids such as (meth) acrylic acid, crotonic acid, or ⁇ -chloroacrylic acid, and unsaturated acids such as maleic acid or fumaric acid. Examples thereof include compounds having a carboxyl group such as saturated dicarboxylic acid and having an ethylenically unsaturated double bond. Moreover, what half-esterified the anhydride of unsaturated dicarboxylic acid, such as maleic anhydride, with the (meth) acrylic compound which has hydroxyl groups, such as hydroxyalkyl (meth) acrylate, can also be used. Among these, (meth) acrylic acid is more preferable, and methacrylic acid is most preferable from the viewpoint of polymerizability (ease of control of molecular weight and the like). These can be used alone or in combination of two or more.
  • the structural unit (Db2) has a cyclic structure with an aromatic ring group represented by the formula (D-2) or (D-3), and has an affinity for a pigment or a pigment composition comprising a pigment and a dispersant, etc. Functions as a site.
  • the structural unit (Db2) is 20 to 80% by weight from the viewpoints of developability and filter segment quality. If it is less than 20% by weight, there is a problem that a high-quality color filter cannot be obtained and the resistance of the filter segment is deteriorated due to insufficient affinity sites for the pigment or the pigment composition comprising the pigment and the dispersant. On the other hand, if it exceeds 80% by weight, the dissolution rate in an alkaline developer becomes slow, and the development time is long and the productivity of the color filter is deteriorated.
  • the bromine atom contained in the structure of the pigment (A1) represented by the formula (1) has a higher polarizability than the chlorine atom. Therefore, the structural unit (Db2) containing an aromatic ring group has a stronger interaction such as affinity than that of its ⁇ -electron system to a chlorinated diketopyrrolopyrrole pigment (CI Pigment Red 254). I can expect that.
  • R represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms which may have a benzene ring.
  • the broken line in formula (D-3) represents a cyclic structure containing one or more saturated or unsaturated heterocycles which may have a substituent, adjacent to the benzene ring.
  • Examples of the precursor of the structural unit (Db2) include styrene, ⁇ -methylstyrene, divinylbenzene, indene, acetyl naphthene, benzyl acrylate, benzyl methacrylate, bisphenol A diglycidyl ether di (meth) acrylate, and methylolated melamine ( Examples thereof include monomers and oligomers such as (meth) acrylic acid esters, and ethylenically unsaturated monomers represented by the formula (D-6).
  • R 1 is a hydrogen atom or a methyl group
  • R 2 is an alkylene group having 2 or 3 carbon atoms
  • R 3 may have a benzene ring.
  • n is an integer of 1 to 15.
  • the alkyl group of R 3 has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms.
  • the alkyl group includes not only a linear alkyl group but also a branched alkyl group and an alkyl group having a benzene ring as a substituent.
  • the alkyl group of R 3 becomes an obstacle and suppresses the approach between the resins and promotes the adsorption / orientation of the resin to the pigment, but when the carbon number exceeds 10, The steric hindrance effect of the group becomes high, and it tends to prevent even the adsorption / orientation of the benzene ring to the pigment. This tendency becomes more prominent as the carbon chain length of the alkyl group of R 3 becomes longer. When the carbon number exceeds 20, the adsorption / orientation of the benzene ring is extremely reduced.
  • Examples of the alkyl group having a benzene ring represented by R 3 include a benzyl group and a 2-phenyl (iso) propyl group.
  • n is preferably an integer of 1 to 15.
  • n is particularly preferably 1 to 4.
  • the precursor of the structural unit (D-b2) styrene, ⁇ -methylstyrene, benzyl acrylate, benzyl methacrylate, or a compound represented by the formula (D) from the viewpoints of copolymerization with other precursors and pigment dispersibility.
  • the ethylenically unsaturated monomer represented by -6) is preferred.
  • the side chain benzene ring is oriented to the pigment, thereby promoting the resin adsorption to the pigment and further suppressing the aggregation of the pigment.
  • benzyl acrylate and / or benzyl methacrylate are most preferred from the viewpoints of developability and dispersion stability.
  • the structural unit (Db3) has a cyclic structure with an aliphatic ring group represented by the following formulas (D-4) and (D-5), and is a pigment or a pigment composition comprising a pigment and a dispersant. It functions as an affinity site and as a hydrophobic site for an alkaline developer. Based on the weight of all the structural units of the resin (D-B1), the structural unit (Db3) is 2 to 60% by weight from the viewpoints of developability, filter segment quality and dispersion stability.
  • the affinity part for the pigment or the pigment composition composed of the pigment and the dispersant is insufficient, and a high-quality color filter cannot be obtained, and the storage stability of the color filter coloring composition is low.
  • the problem of worsening occurs, and the hydrophobicity at the time of development is insufficient, resulting in the problem of pattern peeling or chipping in the pixel portion.
  • it exceeds 60% by weight the dissolution rate in an alkaline developer will be slow, the development time will be long, and the productivity of the color filter will deteriorate.
  • the dicyclopentane moiety in the structure of the structural unit (Db3) is expected to give a steric hindrance to the mutual aggregation state of the molecules in the filter segment without the ring having a planar structure. it can.
  • Examples of the precursor of the structural unit (Db3) include an ethylenically unsaturated monomer represented by the following formula (D-7) or an ethylenically unsaturated monomer represented by the following formula (D-8). It is done.
  • R 1 is a hydrogen atom or a methyl group
  • R 2 is an alkylene group having 2 or 3 carbon atoms
  • m is 0 to It is an integer of 2.
  • ethylenically unsaturated monomer represented by the formula (D-8) for example, FANCLIL manufactured by Hitachi Chemical Co., Ltd.
  • the other structural units are structural units other than the structural unit (Db1), the structural unit (Db2), and the structural unit (Db3).
  • Examples of other structural unit precursors include: Methyl (meth) methacrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, s-butyl (meth) acrylate, t-butyl (Meth) acrylate, pentyl (meth) acrylate, isopentyl acrylate, neopentyl (meth) acrylate, t-pentyl (meth) acrylate, 1-methylbutyl (meth) acrylate, hexyl (meth) acrylate, hepta (meth) acrylate, octyl (Meth) acrylate, 2-ethylhexyl (meth) acrylate, lauryl (meth) acrylate, cetyl (meth) acryl
  • Examples of other ethylenically unsaturated monomers include: (Meth) acrylates having a heterocyclic substituent such as tetrahydrofurfuryl (meth) acrylate or 3-methyloxetanyl (meth) acrylate; Alkoxypolyalkylene glycol (meth) acrylates such as methoxypolypropylene glycol (meth) acrylate or ethoxypolyethylene glycol (meth) acrylate; or (Meth) acrylamide, N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, N-isopropyl (meth) acrylamide, diacetone (meth) acrylamide, acryloylmorpholine, N-hydroxymethyl (meth) Examples include (meth) acrylamides such as acrylamide and N-vinylformamide, and acrylonitrile.
  • Vinyl ethers such as ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, isobutyl vinyl ether, hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol trivinyl ether; or Examples include vinyl acetate, and fatty acid vinyls such as vinyl propionate.
  • the structural unit other than the acrylic structural unit may be used in combination with the acrylic structural unit.
  • an ethylenically unsaturated monomer having an epoxy group or an ethylenic group having a hydroxyl group can also be used. These may become structural units other than other structural units depending on the modification, so that the final structural unit (Db1), structural unit (Db2), and structural unit (Db3) It is desirable to consider the weight ratio.
  • Examples of the method (Di) include a copolymer obtained by copolymerizing an ethylenically unsaturated monomer having an epoxy group and one or more other ethylenically unsaturated monomers.
  • the side chain epoxy group is allowed to undergo an addition reaction with an unsaturated monobasic acid carboxyl group having an ethylenically unsaturated double bond.
  • the carboxyl group of the unsaturated monobasic acid used in this step forms an ester bond after the addition reaction to the epoxy group, it does not fall under the structural unit (D-b1) of the resin (D-B1). Since the polybasic acid anhydride forms a carboxyl group after reaction with a hydroxyl group, it corresponds to the structural unit (Db1) of the resin (D-B1).
  • Examples of ethylenically unsaturated monomers having an epoxy group, unsaturated monobasic acids, and polybasic acid anhydrides include ethylenically unsaturated monomers, unsaturated monobasic acids in the fifth embodiment, and Examples thereof include ethylenically unsaturated monomers, unsaturated monobasic acids, and polybasic acid anhydrides similar to those of polybasic acid anhydrides.
  • Examples of the ethylenically unsaturated monomer having a hydroxyl group and the ethylenically unsaturated monomer having an isocyanate group include an ethylenically unsaturated monomer having a hydroxyl group and an ethylenic group having an isocyanate group in the fifth embodiment. Examples thereof include an ethylenically unsaturated monomer having a hydroxyl group similar to the unsaturated monomer and an ethylenically unsaturated monomer having an isocyanate group.
  • the weight average molecular weight (Mw) of the resin (D-B1) is preferably in the range of 5,000 to 100,000, more preferably 5,000 to 80,000, and still more preferably 5,000 to 30. , 000.
  • the number average molecular weight (Mn) is preferably in the range of 5,000 to 50,000, and the value of Mw / Mn is preferably 10 or less.
  • the resin (D-B1) content is preferably 30 parts by weight or more with respect to 100 parts by weight of the pigment (A1) represented by the formula (1) because the film-forming property and various resistances are good. Since the colorant concentration is high and good color characteristics can be expressed, it is preferably used in an amount of 500 parts by weight or less. More preferably, it is used in an amount of 50 to 250 parts by weight.
  • the coloring composition may further contain other resins other than the resin (D-B1).
  • the other resin is preferably a resin having a transmittance of preferably 80% or more, more preferably 95% or more in the entire wavelength region of 400 to 700 nm in the visible light region.
  • Other resins include thermoplastic resins, thermosetting resins, and photosensitive resins, and these can be used alone or in admixture of two or more. Examples of the resin include the same resins as those in the fifth embodiment.
  • the photosensitive resin examples include (meth) acrylic compounds having a reactive substituent such as an isocyanate group, an aldehyde group, and an epoxy group on a linear polymer having a reactive substituent such as a hydroxyl group, a carboxyl group, or an amino group, A resin obtained by reacting an acid and introducing a photocrosslinkable group such as a (meth) acryloyl group or a styryl group into the linear polymer is used.
  • a reactive substituent such as an isocyanate group, an aldehyde group, and an epoxy group on a linear polymer having a reactive substituent such as a hydroxyl group, a carboxyl group, or an amino group
  • a resin obtained by reacting an acid and introducing a photocrosslinkable group such as a (meth) acryloyl group or a styryl group into the linear polymer is used.
  • a linear polymer containing an acid anhydride such as a styrene-maleic anhydride copolymer or an ⁇ -olefin-maleic anhydride copolymer is converted into a (meth) acrylic compound having a hydroxyl group such as hydroxyalkyl (meth) acrylate.
  • Half-esterified products are also used.
  • the solvent is a filter in which the pigment (A) is sufficiently dispersed in the binder resin (DB), and the colored composition is applied on a substrate such as a glass substrate so that the dry film thickness is 0.2 to 5 ⁇ m. Used to facilitate the formation of segments.
  • the solvent an organic solvent is preferable. The preferred amount of solvent used is the same as in the fifth embodiment.
  • the colored composition of the sixth embodiment can be produced by the same production method as the colored composition of the fifth embodiment.
  • the coloring composition of the sixth embodiment includes a pigment dispersant (DC), a photopolymerization initiator (DD), a sensitizer, a photopolymerizable compound, a polyfunctional thiol, an ultraviolet absorber, and a polymerization prohibition.
  • Optional components such as an agent, a storage stabilizer, and other additives can be contained. Specific examples of these optional components are the same as in the fifth embodiment. Moreover, a preferable example, preferable usage-amount, etc. are the same as that of the 5th embodiment.
  • the colored composition according to the sixth embodiment preferably removes coarse particles in the same manner as the colored composition according to the third embodiment.
  • colorants other pigments
  • other colorants other pigments
  • red dyes examples include xanthene, monoazo (pyridone, barbituric acid, metal complex, etc.), disazo, and anthraquinone.
  • xanthene examples include xanthene, monoazo (pyridone, barbituric acid, metal complex, etc.), disazo, and anthraquinone.
  • C.I. I. And salt forming compounds of xanthene acid dyes such as Acid Red 52, 87, 92, 289 and 338. These can be used alone or in admixture of two or more.
  • preferred colorants to be used in combination include anthraquinone pigments, monoazo pigments, disazo pigments, xanthene dyes, and the like.
  • organic solvent examples include ethyl lactate, benzyl alcohol, 1,2,3-trichloropropane, 1,3-butanediol, 1,3-butylene glycol, and 1,3-butylene glycol.
  • the dispersibility of the coloring agent, the penetrability, and the coating property of the coloring composition are good, so that alkyl lactates such as ethyl lactate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate It is preferable to use glycol acetates such as ethylene glycol monoethyl ether acetate, alcohols such as benzyl alcohol and diacetone alcohol, and ketones such as cyclohexanone.
  • alkyl lactates such as ethyl lactate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate
  • glycol acetates such as ethylene glycol monoethyl ether acetate
  • alcohols such as benzyl alcohol and diacetone alcohol
  • ketones such as cyclohexanone.
  • the resin-type dispersant has a pigment-affinity part having the property of adsorbing to the colorant and a part compatible with the colorant carrier, and adsorbs to the colorant to disperse the colorant to the colorant carrier. It works to stabilize.
  • resin-type dispersants include polycarboxylic acid esters such as polyurethane and polyacrylate, unsaturated polyamides, polycarboxylic acids, polycarboxylic acid (partial) amine salts, polycarboxylic acid ammonium salts, and polycarboxylic acid alkylamine salts.
  • Oil-soluble dispersants such as (meth) acrylic acid-styrene copolymer, (meth) acrylic acid- (meth) acrylic ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol, polyvinylpyrrolidone, etc.
  • Resin water-soluble polymer, polyester, modified poly Acrylate-based, ethylene oxide / propylene oxide addition compound, phosphate ester-based or the like is used. These can be used alone or in admixture of two or more, but are not necessarily limited thereto.
  • resin-type dispersants include Disperbyk-101, 103, 107, 108, 110, 111, 112, 116, 130, 140, 142, 154, 161, 162, 163, 164, 165 manufactured by Big Chemie Japan.
  • SOLSPERSE-3000 9000, 13000, 13240, 13650, 13940, 16000, 17000, 18000, 20000, 21000, 24000, 26000, 27000, 28000, 31845, 32000, 32500, 32550, 33500, 32600, 34750, 35100, 36600, 38500, 41000, 41090, 53095, 55000, 56000, 76500, etc., EFKA-46, 47, 48, 452, 4008, 4009, 4010, 4015, 4020, 4047, 4050 manufactured by Ciba Japan 4055, 4060, 4080, 4400, 4401, 4402, 4403, 4406, 4408, 4300, 4310, 4320, 433 , 4340, 450, 451, 453, 4540, 4550, 4560, 4800, 5010, 5065, 5066, 5070, 7500, 7554, 1101, 120, 150, 1501, 1502, 1503, etc.
  • DISPARLON 3600N DISPARLON 1850 manufactured by Enomoto Kasei Co., Ltd.
  • These can be used alone or in admixture of two or more.
  • a resin-type pigment dispersant having an acidic functional group Disperbyk-108, 110, 111, 112, 116, 142, 180, 2000, 2001 or Nippon Lubrizol, manufactured by Big Chemie Japan SOLSPERSE-3000, 21000, 26000, 36600, 41000 manufactured by Ciba Japan Co., Ltd., DEFKA-4401, 4550 manufactured by Ciba Japan, DISPARLON 3600N, DISPARLON 1850 manufactured by Enomoto Kasei Co., Ltd.
  • Surfactants include sodium lauryl sulfate, polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium stearate, sodium alkyl naphthalene sulfonate, sodium alkyl diphenyl ether disulfonate
  • Anionic surfactants such as lauryl sulfate monoethanolamine, lauryl sulfate triethanolamine, ammonium lauryl sulfate, monoethanolamine stearate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate ester; Polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene Nonionic surfactants such as alkyl ether phosphates, polyoxyethylene sorbitan monostea
  • Photopolymerizable monomer photopolymerizable compound
  • Monomers and oligomers that are cured by ultraviolet rays or heat to produce transparent resins 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, tripropylene glycol di ( (Meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, 1,6-hexaned
  • photopolymerization initiator examples include 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1- Hydroxycyclohexyl phenyl ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1
  • Acetophenone compounds such as [4- (4-morpholinyl) phenyl] -1-butanone or 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one; benzoin, benzoin Methyl ether, benzoin ethyl ether, benzoin isopropyl ether, Or a benzoin
  • the photopolymerization initiator preferably includes at least one photopolymerization initiator selected from the group consisting of acetophenone compounds, phosphine compounds, imidazole compounds, and oxime ester compounds.
  • the photopolymerization initiator By including these photopolymerization initiators, the pattern shape and linearity of the filter segment become better.
  • Sensitizers include chalcone derivatives, unsaturated ketones such as dibenzalacetone, 1,2-diketone derivatives such as benzyl and camphorquinone, benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, anthraquinone derivatives , Xanthene derivatives, thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, oxonol derivatives and other polymethine dyes, acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indoline derivatives, Azulene derivatives, azurenium derivatives, squarylium derivatives, porphyrin derivatives, tetraphenylporphyrin derivatives, triarylmethane
  • Multifunctional thiol examples include hexanedithiol, decanedithiol, 1,4-butanediol bisthiopropionate, 1,4-butanediol bisthioglycolate, ethylene glycol bisthioglycolate, ethylene glycol bisthiopropionate , Trimethylolpropane tristhioglycolate, trimethylolpropane tristhiopropionate, trimethylolethane tris (3-mercaptobutyrate), trimethylolpropane tris (3-mercaptobutyrate), trimethylolpropane tris (3-mercapto) Propionate), pentaerythritol tetrakisthioglycolate, pentaerythritol tetrakisthiopropionate, pentaerythritol tetrakis (3-mercaptopropionate) Dipentaerythrito
  • UV absorber examples include 2- [4-[(2-hydroxy-3- (dodecyl and tridecyl) oxypropyl) oxy] -2-hydroxyphenyl] -4,6-bis (2,4-dimethylphenyl). -1,3,5-triazine, 2- (2-hydroxy-4- [1-octyloxycarbonylethoxy] phenyl) -4,6-bis (4-phenylphenyl) -1,3,5-triazine, etc.
  • polymerization inhibitor examples include hydroquinone such as methyl hydroquinone, t-butyl hydroquinone, 2,5-di-t-butyl hydroquinone, 4-benzoquinone, 4-methoxyphenol, 4-methoxy-1-naphthol and t-butylcatechol.
  • hydroquinone such as methyl hydroquinone, t-butyl hydroquinone, 2,5-di-t-butyl hydroquinone, 4-benzoquinone, 4-methoxyphenol, 4-methoxy-1-naphthol and t-butylcatechol.
  • phenolic compounds such as phenothiazine, bis- (1-dimethylbenzyl) phenothiazine, 3,7-dioctylphenothiazine, copper dibutyldithiocarbamate, copper diethyldithiocarbamate, manganese diethyldithiocarbamate, manganese diphenyldithiocarbamate, etc.
  • manganese salt compounds 4-nitrosophenol, N-nitrosodiphenylamine, N-nitrosocyclohexylhydroxylamine, N-nitrosophenylhydroxylamine Nitroso compounds and their ammonium salts or aluminum salts and the like. These polymerization inhibitors can be used singly or in combination of two or more at any ratio as required.
  • the “antioxidant” may be a compound having an ultraviolet absorbing function, a radical scavenging function, or a peroxide decomposing function.
  • an antioxidant hindered phenols, hindered amines, phosphorus-based compounds are used.
  • Sulfur-based, benzotriazole-based, benzophenone-based, hydroxylamine-based, salicylate-based, and triazine-based compounds, and known ultraviolet absorbers, antioxidants, and the like can be used. These antioxidants can be used singly or as a mixture of two or more at any ratio as required.
  • a hindered phenol antioxidant a hindered amine antioxidant, a phosphorus antioxidant, or a sulfur antioxidant is preferable from the viewpoint of achieving both transmittance and sensitivity of the coating film.
  • Agents More preferably, they are hindered phenolic antioxidants, hindered amine antioxidants, or phosphorus antioxidants.
  • amine compounds examples include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 4 And 2-ethylhexyl dimethylaminobenzoate and N, N-dimethylparatoluidine. These amine compounds can be used singly or in combination of two or more at any ratio as required.
  • dimethylsiloxane having a polyether structure or a polyester structure in the main chain is preferable.
  • dimethylsiloxane having a polyether structure in the main chain include FZ-2122 manufactured by Toray Dow Corning, BYK-333 manufactured by BYK Chemie.
  • dimethylsiloxane having a polyester structure in the main chain include BYK-310 and BYK-370 manufactured by BYK Chemie.
  • Dimethylsiloxane having a polyether structure in the main chain and dimethylsiloxane having a polyester structure in the main chain can be used in combination.
  • a leveling agent is a kind of so-called surfactant having a hydrophobic group and a hydrophilic group in the molecule, having a hydrophilic group but low solubility in water, and when added to a coloring composition, It has the characteristics of low surface tension reduction ability, and it is useful to have good wettability to the glass plate despite its low surface tension reduction ability. Those that can sufficiently suppress the chargeability can be preferably used.
  • dimethylpolysiloxane having a polyalkylene oxide unit can be preferably used.
  • the polyalkylene oxide unit include a polyethylene oxide unit and a polypropylene oxide unit, and dimethylpolysiloxane may have both a polyethylene oxide unit and a polypropylene oxide unit.
  • the bonding form of the polyalkylene oxide unit with dimethylpolysiloxane includes a pendant type in which the polyalkylene oxide unit is bonded in the repeating unit of dimethylpolysiloxane, a terminal-modified type in which the end of dimethylpolysiloxane is bonded, and dimethylpolysiloxane. Any of linear block copolymer types in which they are alternately and repeatedly bonded may be used.
  • Dimethylpolysiloxanes having polyalkylene oxide units are commercially available from Toray Dow Corning Co., Ltd., for example, FZ-2110, FZ-2122, FZ-2130, FZ-2166, FZ-2191, FZ-2203, FZ -2207, but is not limited thereto.
  • a leveling agent can be used individually by 1 type or in mixture of 2 or more types by arbitrary ratios as needed.
  • ⁇ Anionic, cationic, nonionic or amphoteric surfactants can be supplementarily added to the leveling agent. Two or more kinds of surfactants may be mixed and used.
  • Anionic surfactants added to the leveling agent as auxiliary agents include polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium alkyl naphthalene sulfonate, alkyl diphenyl ether disulfonic acid Sodium, lauryl sulfate monoethanolamine, lauryl sulfate triethanolamine, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate Examples include esters.
  • Nonionic surfactants added to the leveling agent as auxiliary agents include polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate ester, polyoxyethylene sorbitan monostearate And amphoteric surfactants such as alkyl dimethylamino acetic acid betaine and alkylimidazolines, and fluorine-based and silicone-based surfactants.
  • the curing agent phenolic resins, amine compounds, acid anhydrides, active esters, carboxylic acid compounds, sulfonic acid compounds and the like are effective, but are not particularly limited to these, and thermosetting resins. Any curing agent may be used as long as it can react with the. Of these, compounds having two or more phenolic hydroxyl groups in one molecule and amine curing agents are preferred.
  • the curing accelerator include amine compounds (for example, dicyandiamide, benzyldimethylamine, 4- (dimethylamino) -N, N-dimethylbenzylamine, 4-methoxy-N, N-dimethylbenzylamine, 4-methyl).
  • Storage stabilizer examples include 2,6-bis (1,1-dimethylethyl) -4-methylphenol, pentaerystyryl-tetrakis [3- (3,5-di-t-butyl-4-hydroxyphenyl).
  • Propionate hindered phenols such as 2,4-bis- (n-octylthio) -6- (4-hydroxy-3,5-di-t-butylanilino) 1,3,5-triazine, t-butylpyrocatechol
  • Organic phosphines such as tetraethylphosphine, triphenylphosphine and tetraphenylphosphine, phosphites such as zinc dimethyldithiophosphate, zinc dipropyldithiophosphate and molybdenum dibutyldithiophosphate, sulfur such as dodecyl sulfide and benzothiophene System, benzyltrimethyl chloride, diethylhydroxyamine, etc. Quaternary ammonium chloride, lactate, and the like organic acids and methyl ethers such as oxalic acid.
  • These storage stabilizers can be used singly or as a mixture of two or more at any
  • adhesion improver examples include vinyl silanes such as vinyltris ( ⁇ -methoxyethoxy) silane, vinylethoxysilane, vinyltrimethoxysilane, (meth) acrylsilanes such as ⁇ -methacryloxypropyltrimethoxysilane, ⁇ - (3 , 4-epoxycyclohexyl) ethyltrimethoxysilane, ⁇ - (3,4-epoxycyclohexyl) methyltrimethoxysilane, ⁇ - (3,4-epoxycyclohexyl) ethyltriethoxysilane, ⁇ - (3,4-epoxycyclohexyl) ) Epoxysilanes such as methyltriethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropyltriethoxysilane, N- ⁇ (aminoethoxyethoxy)
  • the color filter of the seventh embodiment is formed using the above color filter coloring composition. According to the seventh embodiment, it is possible to provide a high-definition color filter excellent in brightness and contrast ratio.
  • the color filter of the seventh embodiment can be used for a color liquid crystal display device, a color image pickup tube element, and the like.
  • the color filter includes a red filter segment, a green filter segment, and a blue filter segment, and the red filter segment therein is formed from the above colored composition.
  • the color filter may further include a magenta filter segment, a cyan filter segment, and a yellow filter segment.
  • a color filter generally includes the above filter segment on a transparent substrate.
  • a transparent substrate glass plates such as soda lime glass, low alkali borosilicate glass and non-alkali alumino borosilicate glass, and resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate are used.
  • a transparent electrode made of indium oxide, tin oxide, or the like may be formed on the surface of the glass plate or the resin plate in order to drive the liquid crystal after forming the panel.
  • the dry film thickness of the filter segment is preferably 0.2 to 10 ⁇ m, more preferably 0.2 to 5 ⁇ m.
  • a vacuum dryer, a convection oven, an IR oven, a hot plate, or the like may be used.
  • the green filter segment can be formed using a normal green coloring composition containing a green pigment and a colorant carrier.
  • a green pigment examples include C.I. I. Pigment Green 7, 10, 36, 37, 58, etc. are used.
  • a yellow pigment or a yellow dye can be used in combination with the green coloring composition.
  • yellow pigments that can be used in combination include C.I. I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177,
  • the blue filter segment can be formed using a normal blue coloring composition containing a blue pigment and a colorant carrier.
  • blue pigments include C.I. I. Pigment Blue Agate 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 22, 60, 64, etc. are used.
  • a purple pigment can be used in combination with the blue coloring composition.
  • purple pigments that can be used in combination include C.I. I. And violet pigments such as CI Pigment Violet V1,19,23,27,29,30,32,37,40,42,50.
  • a basic dye or a salt-forming compound of an acid dye exhibiting blue or purple can be used.
  • a xanthene dye is preferable in terms of heat resistance and lightness.
  • the color filter can be manufactured by a printing method or a photolithography method.
  • the formation of the filter segment by the printing method allows patterning by simply repeating the printing and drying of the coloring composition prepared as a printing ink, and therefore, as a method for producing a color filter, it is low in cost and excellent in mass productivity. Furthermore, it is possible to print a fine pattern having high dimensional accuracy and smoothness by the development of printing technology. In order to perform printing, it is preferable that the ink does not dry and solidify on the printing plate or on the blanket. It is also desirable to control the fluidity of the ink on the printing press, and the ink viscosity can be adjusted with a dispersant or extender pigment.
  • the colored composition prepared as a solvent developing type or alkali developing type colored resist material is applied on a transparent substrate by spray coating, spin coating, slit coating, roll coating or the like. Depending on the method, coating is performed so that the dry film thickness is 0.2 to 10 ⁇ m, preferably 0.2 to 5 ⁇ m. If necessary, the dried film is exposed to ultraviolet light through a mask having a predetermined pattern provided in contact with or non-contact with the film. Then, after immersing in a solvent or alkali developer or spraying the developer by spraying or the like to remove the uncured portion to form a desired pattern, the same operation is repeated for other colors to produce a color filter. be able to. Furthermore, in order to accelerate the polymerization of the colored resist material, heating can be performed as necessary. According to the photolithography method, a color filter with higher accuracy than the above printing method can be manufactured.
  • the filter segment can be formed by immersing in a solvent or an alkaline developer, or spraying the developer with a spray or the like to remove an uncured portion to form a desired pattern. Furthermore, in order to accelerate the polymerization of the filter segment formed by development, heating can be performed as necessary. According to the photolithography method, a filter segment with higher accuracy than the printing method can be formed.
  • an aqueous solution such as sodium carbonate or sodium hydroxide is used as an alkali developer, and an organic alkali such as dimethylbenzylamine or triethanolamine can also be used.
  • an antifoamer and surfactant can also be added to a developing solution.
  • a development processing method a shower development method, a spray development method, a dip (immersion) development method, a paddle (liquid accumulation) development method, or the like can be applied.
  • a water-soluble or alkaline water-soluble resin such as polyvinyl alcohol or a water-soluble acrylic resin is applied and dried to form a film that prevents polymerization inhibition by oxygen. Thereafter, ultraviolet exposure can also be performed.
  • the color filter can be produced by an electrodeposition method, a transfer method, or the like in addition to the above method, but the above-described colored composition or photosensitive colored composition can be used in any method.
  • the electrodeposition method is a method for producing a color filter by using a transparent conductive film formed on a substrate and forming each color filter segment on the transparent conductive film by electrophoresis of colloidal particles.
  • the transfer method is a method in which a filter segment is formed in advance on the surface of a peelable transfer base sheet, and this filter segment is transferred to a desired substrate.
  • coloring composition can be used in any method, but the coloring compositions of the fifth and sixth embodiments are particularly suitable for the photolithography method.
  • a black matrix can be formed in advance before forming each color filter segment on a transparent substrate or a reflective substrate.
  • a chromium, chromium / chromium oxide multilayer film, an inorganic film such as titanium nitride, or a resin film in which a light-shielding agent is dispersed is used, but is not limited thereto.
  • a thin film transistor (TFT) may be formed in advance on the transparent substrate or the reflective substrate, and then each color filter segment may be formed.
  • An overcoat film, a transparent conductive film, a columnar spacer, a liquid crystal alignment film, and the like are formed on the color filter as necessary.
  • the color filter is bonded to the counter substrate using a sealant, and after injecting liquid crystal from the injection port provided in the seal part, the injection port is sealed, and if necessary, a polarizing film or a retardation film is placed outside the substrate.
  • a liquid crystal display panel is manufactured by bonding.
  • Such liquid crystal display panels include twisted nematic (TN), super twisted nematic (STN), in-plane switching (IPS), vertical alignment (VA), and optically convented bend (OCB). It can be used in a liquid crystal display mode in which colorization is performed using a color filter such as the above.
  • the average primary particle diameter of the produced pigment composition was measured (calculated) by the following method.
  • the average primary particle diameter of the pigment was measured by a method of directly measuring the size of primary particles from an electron micrograph using a transmission (TEM) electron microscope. Specifically, the minor axis diameter and major axis diameter of the primary particles of each pigment were measured, and the average was taken as the particle diameter of the primary pigment particles.
  • the volume (weight) of each particle was obtained by approximating the obtained particle size cube, and the volume average particle size was defined as the average primary particle size.
  • the mass average molecular weight of the acrylic resin was measured by the following method.
  • the mass average molecular weight (Mw) of the acrylic resin was measured using a TSKgel column (manufactured by Tosoh Corporation) and GPC equipped with an RI detector (manufactured by Tosoh Corporation, HLC-8120GPC) using THF as a developing solvent.
  • the solution was added in small portions. At this time, the rate of addition of the alkali metal salt of the diketopyrrolopyrrole compound at 75 ° C. while cooling so that the temperature of the mixture of methanol, acetic acid and water is always kept at ⁇ 5 ° C. or lower. was added in small portions over approximately 120 minutes. After addition of the alkali metal salt, red crystals were precipitated to form a red suspension. Subsequently, the obtained red suspension was washed with an ultrafiltration device at 5 ° C. and then filtered to obtain a red paste. This paste was re-dispersed in 3500 parts of methanol cooled to 0 ° C.
  • ⁇ Method for producing diketopyrrolopyrrole pigment composition> (Specific hetero diketopyrrolopyrrole pigment mixture 1 (RC-1))
  • RC-1 Specific hetero diketopyrrolopyrrole pigment mixture 1
  • a stainless steel reaction vessel equipped with a reflux tube 200 parts of tert-amyl alcohol dehydrated with molecular sieves and 140 parts of sodium tert-amyl alkoxide are added in a nitrogen atmosphere, and heated to 100 ° C. with stirring to obtain an alcoholate solution.
  • 88 parts of diisopropyl succinate, 104.5 parts of 4-chlorobenzonitrile and 15.1 parts of 4-cyanobiphenyl are added to a glass flask and heated to 90 ° C. with stirring to dissolve them. A solution of was prepared.
  • the solution was added in small portions. At this time, the rate of addition of the alkali metal salt of the diketopyrrolopyrrole compound at 75 ° C. while cooling so that the temperature of the mixture of methanol, acetic acid and water is always kept at ⁇ 5 ° C. or lower. was added in small portions over approximately 120 minutes. After addition of the alkali metal salt, red crystals were precipitated to form a red suspension. Subsequently, the obtained red suspension was washed with an ultrafiltration device at 5 ° C. and then filtered to obtain a red paste. This paste was re-dispersed in 3500 parts of methanol cooled to 0 ° C.
  • Green photosensitive coloring composition 1 (GR-1)) The following mixture was stirred and mixed so as to be uniform, then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) using zirconia beads having a diameter of 0.5 mm, and then 5.0 ⁇ m.
  • the green colored composition 1 (GP-1) was produced by filtration using a filter.
  • Green pigment (CI Pigment Green 36) 6.8 parts Yellow pigment (CI Pigment Yellow 150) 5.2 parts
  • Resin-type dispersant (“EFKA4300” manufactured by Ciba Japan) 1.0 parts Acrylic resin Solution 1 35.0 parts Propylene glycol monomethyl ether acetate 52.0 parts
  • Green coloring composition 1 (GP-1) 42.0 parts Acrylic resin solution 2 13.2 parts Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 2.8 parts Photopolymerization initiator (Ciba Japan) "Irgacure 907" manufactured by the company) 2.0 parts Sensitizer ("EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts 39.6 parts ethylene glycol monomethyl ether acetate
  • blue photosensitive coloring composition 1 (BR-1).
  • Blue coloring composition 1 (BP-1) 34.0 parts Acrylic resin solution 2 15.2 parts Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 3.3 parts Photopolymerization initiator (Ciba Japan) "Irgacure 907” manufactured by the company) 2.0 parts Sensitizer ("EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts 45.1 parts ethylene glycol monomethyl ether acetate
  • Example 1 (Production of Pigment Composition 1 (R-1)) 99.0 parts of a brominated diketopyrrolopyrrole pigment of formula (1), 1.0 part of a specific hetero diketopyrrolopyrrole pigment A of formula (A-2-1), 1000 parts of sodium chloride, and 120 parts of diethylene glycol are mixed with stainless steel. It was charged in a 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 10 hours. Next, the kneaded mixture is put into warm water, stirred for 1 hour while heating to about 80 ° C.
  • a 1 gallon kneader manufactured by Inoue Seisakusho
  • Example 2 (Production of Pigment Composition 2 (R-2)) 99.0 parts of brominated diketopyrrolopyrrole pigment of formula (1) and 1.0 part of specific hetero diketopyrrolopyrrole pigment A of formula (A-2-1) are mixed with brominated diketopyrrolopyrrole of formula (1).
  • the diketo was prepared in the same manner as in the production of pigment composition 1 (R-1) except that 97.0 parts of pigment and 3.0 parts of the specific heterodiketopyrrolopyrrole pigment A of formula (A-2-1) were changed. 96.5 parts of pyrrolopyrrole pigment composition 2 (R-2) were obtained.
  • the average primary particle size was 36.8 nm.
  • Example 3 (Production of Pigment Composition 3 (R-3)) 99.0 parts of brominated diketopyrrolopyrrole pigment of formula (1) and 1.0 part of specific hetero diketopyrrolopyrrole pigment A of formula (A-2-1) are mixed with brominated diketopyrrolopyrrole pigment of formula (1)
  • the diketo was prepared in the same manner as in the production of pigment composition 1 (R-1) except that 95.0 parts of pigment and 5.0 parts of the specific heterodiketopyrrolopyrrole pigment A of formula (A-2-1) were changed. 97.2 parts of pyrrolopyrrole pigment composition 3 (R-3) were obtained.
  • the average primary particle size was 30.5 nm.
  • Example 4 (Production of Pigment Composition 4 (R-4)) 99.0 parts of brominated diketopyrrolopyrrole pigment of formula (1) and 1.0 part of specific hetero diketopyrrolopyrrole pigment A of formula (A-2-1) are mixed with brominated diketopyrrolopyrrole of formula (1).
  • the diketo was prepared in the same manner as in the production of pigment composition 1 (R-1) except that 90.0 parts of pigment and 10.0 parts of the specific heterodiketopyrrolopyrrole pigment A of formula (A-2-1) were changed. 96.9 parts of pyrrolopyrrole pigment composition 4 (R-4) were obtained.
  • the average primary particle size was 28.5 nm.
  • Example 5 (Production of Pigment Composition 5 (R-5)) 99.0 parts of brominated diketopyrrolopyrrole pigment of formula (1) and 1.0 part of specific hetero diketopyrrolopyrrole pigment A of formula (A-2-1) are mixed with brominated diketopyrrolopyrrole pigment of formula (1)
  • the diketo was prepared in the same manner as in the production of pigment composition 1 (R-1) except that 85.0 parts of pigment and 15.0 parts of the specific heterodiketopyrrolopyrrole pigment A of formula (A-2-1) were changed. 97.3 parts of pyrrolopyrrole pigment composition 5 (R-5) were obtained.
  • the average primary particle size was 29.5 nm.
  • Example 6 (Production of Pigment Composition 6 (R-6)) Pigment composition 3 (R-3) except that the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2-1) was changed to the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2-2) ) To obtain 98.1 parts of diketopyrrolopyrrole pigment composition 6 (R-6).
  • the average primary particle size was 29.9 nm.
  • Example 7 (Production of Pigment Composition 7 (R-7)) Pigment composition 3 (R-3) except that the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2-1) was changed to the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2-3a) ) To give 98.0 parts of diketopyrrolopyrrole pigment composition 7 (R-7). The average primary particle size was 30.7 nm.
  • Example 8 (Production of Pigment Composition 8 (R-8)) Pigment composition 3 (R-3) except that the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2-1) was changed to the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2-3b) ) To obtain 98.4 parts of diketopyrrolopyrrole pigment composition 8 (R-8).
  • the average primary particle size was 31.2 nm.
  • Example 9 (Production of Pigment Composition 9 (R-9)) Pigment composition 3 (R-3) except that the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2-1) was changed to the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2-4a) ) To obtain 97.5 parts of diketopyrrolopyrrole pigment composition 9 (R-9). The average primary particle size was 35.4 nm.
  • Example 10 (Production of Pigment Composition 10 (R-10)) Pigment composition 3 (R-3) except that the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2-1) was changed to the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2-4b) ) To obtain 96.6 parts of diketopyrrolopyrrole pigment composition 10 (R-10).
  • the average primary particle size was 35.8 nm.
  • Example 11 (Production of Pigment Composition 11 (R-11)) Pigment composition 3 (R-3) except that the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2-1) was changed to the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2-9a) ) To obtain 93.9 parts of a diketopyrrolopyrrole pigment composition 11 (R-11).
  • the average primary particle size was 32.4 nm.
  • Example 12 (Production of Pigment Composition 12 (R-12)) Pigment composition 3 (R-3) except that the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2-1) was changed to the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2-8) ) To obtain 95.7 parts of diketopyrrolopyrrole pigment composition 12 (R-12).
  • the average primary particle size was 29.8 nm.
  • Example 13 (Production of Pigment Composition 13 (R-13)) 98.0 parts of brominated diketopyrrolopyrrole pigment of formula (1), commercially available C.I. I. 1.0 part of Pigment Red 254 (“Irgafoa Red B-CF” manufactured by Ciba Specialty Chemicals), 1.0 part of the specific heterodiketopyrrolopyrrole pigment A of formula (A-2-1), 1000 parts of sodium chloride, and 120 parts of diethylene glycol was charged into a stainless gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 10 hours.
  • the kneaded mixture is put into warm water, stirred for 1 hour while heating to about 80 ° C. to form a slurry, filtered and washed with water to remove salt and diethylene glycol, and then dried at 80 ° C. for one day and pulverized.
  • 96.7 parts of diketopyrrolopyrrole pigment composition 13 (R-13) was obtained.
  • the average primary particle size was 33.2 nm.
  • Example 14 (Production of Pigment Composition 14 (R-14)) 98.0 parts of brominated diketopyrrolopyrrole pigment of formula (1), commercially available C.I. I. 1.0 part of Pigment Red 254 (“Irgafore Red B-CF” manufactured by Ciba Specialty Chemicals), 1.0 part of the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2-1) Brominated diketopyrrolopyrrole pigment 80.0 parts, commercially available C.I. I.
  • Pigment Red 254 (“Irgafoa Red B-CF” manufactured by Ciba Specialty Chemicals) 18.0 parts, pigment composition other than changed to 2.0 parts of specific heterodiketopyrrolopyrrole pigment A of formula (A-2-1)
  • 98.3 parts of diketopyrrolopyrrole pigment composition 14 (R-14) was obtained.
  • the average primary particle size was 30.2 nm.
  • Example 15 (Production of Pigment Composition 15 (R-15)) 98.0 parts of brominated diketopyrrolopyrrole pigment of formula (1), commercially available C.I. I. 1.0 part of Pigment Red 254 (“Irgafoa Red B-CF” manufactured by Ciba Specialty Chemicals), 1.0 part of the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2-1) 50.0 parts of brominated diketopyrrolopyrrole pigment, commercially available C.I. I.
  • Pigment Red 254 (“Irgafore Red B-CF” manufactured by Ciba Specialty Chemicals) 45.0 parts, pigment composition except for specific heterodiketopyrrolopyrrole pigment A5.0 parts of formula (A-2-1)
  • 97.0 parts of diketopyrrolopyrrole pigment composition 15 (R-15) was obtained.
  • the average primary particle size was 26.7 nm.
  • Example 16 (Production of Pigment Composition 16 (R-16)) 98.0 parts of brominated diketopyrrolopyrrole pigment of formula (1), commercially available C.I. I. 1.0 part of Pigment Red 254 (“Irgafore Red B-CF” manufactured by Ciba Specialty Chemicals), 1.0 part of the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2-1) 20.0 parts of brominated diketopyrrolopyrrole pigment, commercially available C.I. I.
  • Pigment Red 254 (“Irgafore Red B-CF” manufactured by Ciba Specialty Chemicals) 72.0 parts, pigment composition other than the specific heterodiketopyrrolopyrrole pigment A 8.0 parts of the formula (A-2-1)
  • 94.8 parts of diketopyrrolopyrrole pigment composition 16 (R-16) were obtained.
  • the average primary particle size was 28.0 nm.
  • Example 17 (Production of Pigment Composition 17 (R-17)) 98.0 parts of brominated diketopyrrolopyrrole pigment of formula (1), commercially available C.I. I. 1.0 part of Pigment Red 254 (“Irgafore Red B-CF” manufactured by Ciba Specialty Chemicals), 1.0 part of the specific heterodiketopyrrolopyrrole pigment A of the formula (A-2-1) 20.0 parts of brominated diketopyrrolopyrrole pigment, commercially available C.I. I.
  • Pigment Red 254 (“Irgafore Red B-CF” manufactured by Ciba Specialty Chemicals) 65.0 parts, pigment composition except for specific heterodiketopyrrolopyrrole pigment A 15.0 parts of formula (A-2-1)
  • 96.2 parts of diketopyrrolopyrrole pigment composition 17 (R-17) was obtained.
  • the average primary particle size was 29.3 nm.
  • Example 18 (Production of Pigment Composition 18 (R-18)) 80.0 parts of brominated diketopyrrolopyrrole pigment of formula (1), 20.0 parts of specific hetero diketopyrrolopyrrole pigment mixture 1 (RC-1), 1000 parts of sodium chloride, and 120 parts of diethylene glycol are made of stainless steel. It was charged in a 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 10 hours. Next, the kneaded mixture is put into warm water, stirred for 1 hour while heating to about 80 ° C.
  • a 1 gallon kneader manufactured by Inoue Seisakusho
  • Example 19 (Production of Pigment Composition 19 (R-19))
  • the specific hetero diketopyrrolopyrrole pigment mixture 1 (RC-1) was changed to the specific hetero diketopyrrolopyrrole pigment mixture 2 (RC-2) in the same manner as in the production of the pigment composition 18 (R-18).
  • 96.1 parts of diketopyrrolopyrrole pigment composition 19 (R-19) was obtained.
  • the average primary particle size was 30.5 nm.
  • Example 20 (Production of Pigment Composition 20 (R-20))
  • the specific hetero diketopyrrolopyrrole pigment mixture 1 (RC-1) was changed to the specific hetero diketopyrrolopyrrole pigment mixture 3 (RC-3) in the same manner as in the production of the pigment composition 18 (R-18).
  • 95.4 parts of diketopyrrolopyrrole pigment composition 20 (R-20) was obtained.
  • the average primary particle size was 31.1 nm.
  • Example 21 (Production of Pigment Composition 21 (R-21)) 95.0 parts of a brominated diketopyrrolopyrrole pigment of formula (1), 5.0 parts of a specific hetero diketopyrrolopyrrole pigment A of formula (A-2-1), 5.0 of a dye derivative of formula (7-1) Parts, 1000 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 10 hours. Next, the kneaded mixture is put into warm water, stirred for 1 hour while heating to about 80 ° C.
  • a 1 gallon kneader manufactured by Inoue Seisakusho
  • Example 22 (Production of Pigment Composition 22 (R-22)) 80.0 parts of brominated diketopyrrolopyrrole pigment of formula (1), commercially available C.I. I. Pigment Red 254 (“Irgafore Red B-CF” manufactured by Ciba Specialty Chemicals) 18.0 parts, specific heterodiketopyrrolopyrrole pigment A 2.0 parts of formula (A-2-1), formula (7-1) A pigment derivative of 5.0 parts, 1000 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 10 hours.
  • C.I. I. Pigment Red 254 (“Irgafore Red B-CF” manufactured by Ciba Specialty Chemicals) 18.0 parts
  • specific heterodiketopyrrolopyrrole pigment A 2.0 parts of formula (A-2-1), formula (7-1) A pigment derivative of 5.0 parts, 1000 parts of sodium
  • the kneaded mixture is put into warm water, stirred for 1 hour while heating to about 80 ° C. to form a slurry, filtered and washed with water to remove salt and diethylene glycol, and then dried at 80 ° C. for one day and pulverized.
  • 91.3 parts of diketopyrrolopyrrole pigment composition 22 (R-22) was obtained.
  • the average primary particle size was 29.1 nm.
  • Pigment Red 254 (“Irgafoa Red B-CF” manufactured by Ciba Specialty Chemicals) 65.0 parts, pigment composition other than the specific heterodiketopyrrolopyrrole pigment A 20.0 parts of the formula (A-2-1) 95.1 parts of diketopyrrolopyrrole pigment composition 26 (R-26) was obtained in the same manner as in Preparation of Compound 13 (R-13). The average primary particle size was 29.5 nm.
  • Example 23 (Preparation of colored composition 1 (RP-1)) The following mixture was stirred and mixed so as to be uniform, then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) using zirconia beads having a diameter of 0.5 mm, and then 5.0 ⁇ m. Then, colored composition 1 (RP-1) was produced.
  • Diketopyrrolopyrrole pigment composition 1 (R-1) 11.0 parts
  • Dye derivative Formula (14-1) 1.0 part Acrylic resin solution 1 40.0 parts Propylene glycol monomethyl ether acetate 48.0 parts
  • Example 45 (Preparation of colored composition 23 (RP-23)) The following mixture was stirred and mixed so as to be uniform, then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) using zirconia beads having a diameter of 0.5 mm, and then 5.0 ⁇ m. Then, a colored composition 23 (RP-23) was produced.
  • Diketopyrrolopyrrole pigment composition 2 (R-2) 11.0 parts
  • Dye derivative Formula (6-3) 1.0 part Resin-type dispersant 6.0 parts (“BYK161" (30% solution) manufactured by Big Chemie) ) Acrylic resin solution 1 31.0 parts Propylene glycol monomethyl ether acetate 51.0 parts
  • Example 46 (Preparation of colored composition 24 (RP-24)) The following mixture was stirred and mixed so as to be uniform, then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) using zirconia beads having a diameter of 0.5 mm, and then 5.0 ⁇ m. A colored composition 24 (RP-24) was produced by filtration using a filter. Diketopyrrolopyrrole pigment composition 2 (R-2) 12.0 parts Resin-type dispersant 3.6 parts (Ajinomoto Fine Techno Co., Ltd. “Ajisper PB821”) Acrylic resin solution 1 23.0 parts Propylene glycol monomethyl ether acetate 61.4 parts
  • the light emitted from the backlight unit for liquid crystal display is polarized through the polarizing plate, passes through the dried coating film of the colored composition applied on the glass substrate, and reaches the polarizing plate. If the polarizing planes of the polarizing plate and the polarizing plate are parallel, light is transmitted through the polarizing plate, but if the polarizing plane is perpendicular, the light is blocked by the polarizing plate.
  • a color luminance meter (“BM-5A” manufactured by Topcon Corporation) was used as the luminance meter, and a polarizing plate (“NPF-G1220DUN” manufactured by Nitto Denko Corporation) was used as the polarizing plate.
  • NPF-G1220DUN manufactured by Nitto Denko Corporation
  • a black mask with a 1 cm square hole was applied to the measurement portion in order to block unnecessary light.
  • ⁇ Viscosity stability evaluation> Measurement of initial viscosity and viscosity increase with time
  • the viscosity stability was evaluated based on the viscosity increase rate with time. If the thickening ratio with time is 80% or more and less than 120%, it can be practically endured. When the viscosity is reduced or increased beyond this range, when the colored composition is applied to the glass substrate, it cannot be applied under the same application conditions, resulting in a problem in productivity. More preferably, it is 90% or more and less than 110%.
  • ⁇ Thickening rate over time 90% or more and less than 110%
  • ⁇ Thickening rate over time 80% or more and less than 90%, or 110% or more and less than 120%
  • ⁇ Thickening rate over time or less than 80% or 120% or more
  • Example 48 to 72 (Preparation of photosensitive coloring compositions 2 to 24 (RR-2 to 24)) Coloring composition 1 (RP-1) was changed to coloring compositions 2 to 24 (RP-2 to 24), and coloring compositions 2 to 24 (RP-2) were used so as to have the same chromaticity as Example 47. To 24) and the colored composition 32 (RP-32), except that the ratio of the colored composition 32 (RP-32) was adjusted to prepare photosensitive colored compositions 2 to 24 (RP-2 to 24).
  • the photosensitive coloring composition was applied to the substrate, dried, and then irradiated with 300 mJ / cm 2 of ultraviolet rays using an ultrahigh pressure mercury lamp. Subsequently, heat treatment was performed at 230 ° C. for 60 minutes, and then heat treatment at 240 ° C. for 60 minutes was repeated twice.
  • the coating film surface of the substrate after the heat treatment was observed with an optical microscope, and the presence or absence of crystal precipitation was determined according to the following criteria.
  • the specific heterodiketopyrrolopyrrole pigment A examples using diketopyrrolopyrrole pigment compositions having a content of 1 to 15% by mass based on the total mass of the diketopyrrolopyrrole pigment are particularly excellent in lightness and high It had a contrast, and it was possible to suppress crystal precipitation of the diketopyrrolopyrrole pigment due to the heating process.
  • a colored coating was formed.
  • the film was irradiated with ultraviolet rays of 300 mJ / cm 2 using a super high pressure mercury lamp through a photomask.
  • spray development was performed with an alkaline developer composed of a 0.2% by weight aqueous sodium carbonate solution to remove unexposed portions, followed by washing with ion-exchanged water. Formed.
  • the average primary particle diameter of the produced pigment composition was measured (calculated) by the following method. Propylene glycol monomethyl ether acetate was added to the powder of the pigment composition, and a small amount of Disperbyk-161 was added as a resin-type dispersant, followed by treatment with ultrasonic waves for 1 minute to prepare a measurement sample. This sample was taken with a transmission (TEM) electron microscope and three photographs (for 3 fields of view) showing the primary particles of 100 or more pigments were taken, and the size of 100 primary particles was measured in order from the upper left. did.
  • TEM transmission
  • the short axis diameter and the long axis diameter of the primary particles of each pigment are measured in nm units, the average is the primary particle diameter of the pigment particles, and a total of 300 distributions are created in increments of 5 nm.
  • a median value in increments of 5 nm was approximated as the particle diameter of those particles, and the number average particle diameter was calculated by calculating based on each particle diameter and the number thereof.
  • Example 1 (Production of Pigment Composition 1 (R-1)) To a stainless steel reaction vessel equipped with a reflux tube, 200 parts of tert-amyl alcohol dehydrated with molecular sieves and 140 parts of sodium tert-amyl alkoxide are added in a nitrogen atmosphere, and heated to 100 ° C. with stirring to obtain an alcoholate solution. Prepared. On the other hand, 88 parts of diisopropyl succinate and 153.6 parts of 4-bromobenzonitrile were added to a glass flask and dissolved by heating to 90 ° C. with stirring to prepare a solution of these mixtures.
  • the solution was added in small portions. At this time, the rate of addition of the alkali metal salt of the diketopyrrolopyrrole compound at 75 ° C. while cooling so that the temperature of the mixture of methanol, acetic acid and water is always kept at ⁇ 5 ° C. or lower. was added in small portions over approximately 120 minutes. After addition of the alkali metal salt, red crystals were precipitated to form a red suspension. Subsequently, the obtained red suspension was washed with an ultrafiltration device at 5 ° C. and then filtered to obtain a red paste. This paste was re-dispersed in 3500 parts of methanol cooled to 0 ° C.
  • the diketopyrrolopyrrole compound aqueous paste obtained by filtering with an ultrafiltration machine was dried at 80 ° C. for 24 hours and pulverized to thereby bromine the diketopyrrolopyrrole of formula (1). 150.8 parts of pigment were obtained.
  • Example 2 (Production of Pigment Composition 2 (R-2)) 95.0 parts of a brominated diketopyrrolopyrrole pigment of formula (1), 5.0 parts of a specific hetero diketopyrrolopyrrole pigment B of formula (B-2-1) obtained during the production of pigment composition 1, sodium chloride 1000 parts and 120 parts of diethylene glycol were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 10 hours. Next, the kneaded mixture is put into warm water, stirred for 1 hour while heating to about 80 ° C.
  • pigment composition 2 which is a diketopyrrolopyrrole pigment composition.
  • the average primary particle size was 30.5 nm.
  • Example 3 (Production of Pigment Composition 3 (R-3)) 95.0 parts of a brominated diketopyrrolopyrrole pigment of the formula (1) and 5.0 parts of a specific hetero diketopyrrolopyrrole pigment B of the formula (B-2-1) are converted into a brominated diketopyrrolopyrrole of the formula (1)
  • the diketo was prepared in the same manner as in the preparation of pigment composition 2 (R-2) except that 90.0 parts of pigment and 10.0 parts of the specific heterodiketopyrrolopyrrole pigment B of formula (B-2-1) were changed.
  • 96.9 parts of pigment composition 3 (R-3) which is a pyrrolopyrrole pigment composition was obtained.
  • the average primary particle size was 26.5 nm.
  • Example 4 (Production of Pigment Composition 4 (R-4)) 95.0 parts of a brominated diketopyrrolopyrrole pigment of the formula (1) and 5.0 parts of a specific hetero diketopyrrolopyrrole pigment B of the formula (B-2-1) are converted into a brominated diketopyrrolopyrrole of the formula (1)
  • the diketo was prepared in the same manner as in the preparation of pigment composition 2 (R-2) except that 85.0 parts of pigment and 15.0 parts of the specific heterodiketopyrrolopyrrole pigment B of formula (B-2-1) were changed.
  • 97.1 parts of pigment composition 4 (R-4), which is a pyrrolopyrrole pigment composition was obtained.
  • the average primary particle size was 28.5 nm.
  • Example 5 (Production of Pigment Composition 5 (R-5)) In pigment composition 1 (R-1), except that 60.2 parts of the benzonitrile compound of the formula (B-3-1) were changed to 54.2 parts of the benzonitrile compound of the formula (B-3-2). In the same manner as in the production of the specific hetero diketopyrrolopyrrole pigment B carried out in Step 8, 85.2 parts of the specific hetero diketopyrrolopyrrole pigment B represented by the formula (B-2-2) was obtained.
  • Example 6 (Production of Pigment Composition 6 (R-6)) First, except that 60.2 parts of the benzonitrile compound of the formula (B-3-1) were changed to 58.2 parts of the benzonitrile compound of the formula (B-3-3), the pigment composition 1 (R-1) In the same manner as in the production of the specific hetero diketopyrrolopyrrole pigment B carried out in the above, 82.2 parts of the specific hetero diketopyrrolopyrrole pigment B represented by the formula (B-2-3) was obtained.
  • Example 7 (Production of Pigment Composition 7 (R-7))
  • the pigment composition 1 (R-1) except that 60.2 parts of the benzonitrile compound of the formula (B-3-1) was changed to 84.1 parts of the benzonitrile compound of the formula (B-3-4a).
  • 94.1 parts of the specific hetero diketopyrrolopyrrole pigment B represented by the formula (B-2-4a) was obtained.
  • Example 8 (Production of Pigment Composition 8 (R-8)) 95.0 parts of the brominated diketopyrrolopyrrole pigment of the formula (1) and 5.0 parts of the specific hetero diketopyrrolopyrrole pigment B of the formula (B-2-4a) are mixed with the brominated diketopyrrolopyrrole of the formula (1) Diketopyrrolo was prepared in the same manner as in the production of Pigment Composition 7 (R-7) except that 85.0 parts of pigment and 15.0 parts of the specific hetero diketopyrrolopyrrole pigment B of formula (B-2-4a) were changed. 96.1 parts of pigment composition 8 (R-8), which is a pyrrole pigment composition, was obtained. The average primary particle size was 25.5 nm.
  • Example 9 (Production of Pigment Composition 9 (R-9)) In pigment composition 1 (R-1), except that 60.2 parts of the benzonitrile compound of the formula (B-3-1) were changed to 71.8 parts of the benzonitrile compound of the formula (B-3-4b) In the same manner as in the production of the specific hetero diketopyrrolopyrrole pigment B carried out in Step 1, 79.1 parts of the specific hetero diketopyrrolopyrrole pigment B represented by the formula (B-2-4b) was obtained.
  • Example 10 (Production of Pigment Composition 10 (R-10)) In pigment composition 1 (R-1), except that 60.2 parts of the benzonitrile compound of the formula (B-3-1) was changed to 49.7 of the benzonitrile compound of the formula (B-3-5) It carried out similarly to manufacture of the specific hetero diketo pyrrolo pyrrole pigment B implemented, and obtained 66.9 parts of specific hetero diketo pyrrolo pyrrole pigment B represented by a formula (B-2-5).
  • Example 11 (Production of Pigment Composition 11 (R-11))
  • pigment composition 1 (R-1) except that 60.2 parts of the benzonitrile compound of the formula (B-3-1) were changed to 106.9 parts of the benzonitrile compound of the formula (B-3-6b) 90.7 parts of the specific hetero diketopyrrolopyrrole pigment B represented by the formula (B-2-6b) was obtained in the same manner as in the production of the specific hetero diketopyrrolopyrrole pigment B performed in the above.
  • Example 12 (Production of Pigment Composition 12 (R-12))
  • the pigment composition 1 (R-1) except that 60.2 parts of the benzonitrile compound of the formula (B-3-1) was changed to 75.6 parts of the benzonitrile compound of the formula (B-3-6c).
  • 100.8 parts of the specific hetero diketopyrrolopyrrole pigment B represented by the formula (B-2-6c) was obtained in the same manner as in the production of the specific hetero diketopyrrolopyrrole pigment B performed in the above.
  • Example 13 (Production of Pigment Composition 13 (R-13))
  • the pigment composition 1 (R-1) except that 60.2 parts of the benzonitrile compound of the formula (B-3-1) was changed to 87.8 parts of the benzonitrile compound of the formula (B-3-7).
  • 85.2 parts of the specific hetero diketopyrrolopyrrole pigment B represented by the formula (B-2-7) was obtained.
  • Example 14 (Production of Pigment Composition 14 (R-14)) 95.0 parts of the brominated diketopyrrolopyrrole pigment of the formula (1) and 5.0 parts of the specific hetero diketopyrrolopyrrole pigment B of the formula (B-2-7) are converted into the brominated diketopyrrolopyrrole of the formula (1) Diketopyrrolo was prepared in the same manner as in the production of pigment composition 13 (R-13) except that 85.0 parts of pigment and 15.0 parts of the specific hetero diketopyrrolopyrrole pigment B of formula (B-2-7) were changed. 95.1 parts of pigment composition 14 (R-14), which is a pyrrole pigment composition, was obtained. The average primary particle size was 26.5 nm.
  • Example 15 (Production of Pigment Composition 15 (R-15))
  • pigment composition 1 (R-1) except that 60.2 parts of the benzonitrile compound of the formula (B-3-1) were changed to 50.0 parts of the benzonitrile compound of the formula (B-3-8).
  • 64.5 parts of the specific hetero diketopyrrolopyrrole pigment B represented by the formula (B-2-8) was obtained.
  • Example 16 (Production of Pigment Composition 16 (R-16)) To a stainless steel reaction vessel equipped with a reflux tube, 200 parts of tert-amyl alcohol dehydrated with molecular sieves and 140 parts of sodium tert-amyl alkoxide are added in a nitrogen atmosphere, and heated to 100 ° C. with stirring to obtain an alcoholate solution. Prepared. Meanwhile, 88 parts of diisopropyl succinate, 146.0 parts of 4-bromobenzonitrile and 7.6 parts of a benzonitrile compound of the formula (B-3-1) are added to a glass flask and heated to 90 ° C. with stirring. And dissolved to prepare solutions of these mixtures.
  • the solution was added in small portions. At this time, the rate of addition of the alkali metal salt of the diketopyrrolopyrrole compound at 75 ° C. while cooling so that the temperature of the mixture of methanol, acetic acid and water is always kept at ⁇ 5 ° C. or lower. was added in small portions over approximately 120 minutes. After addition of the alkali metal salt, red crystals were precipitated to form a red suspension. Subsequently, the obtained red suspension was washed with an ultrafiltration device at 5 ° C. and then filtered to obtain a red paste. This paste was re-dispersed in 3500 parts of methanol cooled to 0 ° C.
  • the diketopyrrolopyrrole compound aqueous paste obtained by filtering off with an ultrafiltration machine was dried at 80 ° C. for 24 hours and pulverized to obtain a diketopyrrolopyrrole pigment composition 145.8. Got a part.
  • the calibration curve necessary for quantification is the brominated diketopyrrolopyrrole pigment of the formula (1) synthesized in the production of the pigment composition 1 (R-1) and the specific heterodiyl of the formula (B-2-1). It was prepared using ketopyrrolopyrrole pigment B.
  • Apparatus JASCO Gulliver series detector; JASCO UV-970 detector column; Waters Symmetry C18 (5 ⁇ m, 2.1 mm ⁇ ⁇ 150 mm) Mobile phase A solution; dimethylformamide / water (1: 1) Mobile phase solution B: dimethylformamide / water (97.5: 2.5) Gladiendo (Liquid B): 47% ⁇ (15min) ⁇ 47% ⁇ (5min) ⁇ 100% ⁇ (25min) ⁇ 100% Wavelength: 510nm Column temperature: 35 ° C Flow rate: 0.3 mL / min Sample injection volume: 5 ⁇ L (dissolved in N-methylpyrrolidone / 28% CH 3 ONa methanol solution) Formula (1) holding time; 11.9 to 12.9 min Formula (B-2-1) retention time; 13.2 to 14.1 min
  • Example 17 (Production of Pigment Composition 17 (R-17)) To a stainless steel reaction vessel equipped with a reflux tube, 200 parts of tert-amyl alcohol dehydrated with molecular sieves and 140 parts of sodium tert-amyl alkoxide are added in a nitrogen atmosphere, and heated to 100 ° C. with stirring to obtain an alcoholate solution. Prepared. Meanwhile, 88 parts of diisopropyl succinate, 146.0 parts of 4-bromobenzonitrile and 7.6 parts of a benzonitrile compound of the formula (B-3-1) are added to a glass flask and heated to 90 ° C. with stirring. And dissolved to prepare solutions of these mixtures.
  • the solution was added in small portions. At this time, the rate of addition of the alkali metal salt of the diketopyrrolopyrrole compound at 75 ° C. while cooling so that the temperature of the mixture of methanol, acetic acid and water is always kept at ⁇ 5 ° C. or lower. was added in small portions over approximately 120 minutes. After addition of the alkali metal salt, red crystals were precipitated to form a red suspension. Subsequently, the obtained red suspension was washed with an ultrafiltration device at 5 ° C. and then filtered to obtain a red paste. This paste was re-dispersed in 3500 parts of methanol cooled to 0 ° C.
  • red paste of a diketopyrrolopyrrole compound was redispersed in 3000 ml of water, and then a pigment derivative slurry in which 5.5 parts of a pigment derivative of a benzoisoindole derivative represented by the formula (7-1) was added to 100 parts of water with stirring. The mixture was added and stirred at 10 ° C. or lower for 1 hour, and then washed by filtration to obtain an aqueous paste of diketopyrrolopyrrole compound. This water paste was dried at 80 ° C. for 24 hours and pulverized to obtain 154.8 parts of a diketopyrrolopyrrole pigment composition.
  • the content of the specific hetero diketopyrrolopyrrole pigment B represented by the formula (1) was quantitatively analyzed using HPLC.
  • the mass ratio of the specific heterodiketopyrrolopyrrole pigment B represented by the formula (9) was 94.8: 5.2.
  • Example 18 (Production of Pigment Composition 18 (R-18)) To a stainless steel reaction vessel equipped with a reflux tube, 200 parts of tert-amyl alcohol dehydrated with molecular sieves and 140 parts of sodium tert-amyl alkoxide are added in a nitrogen atmosphere, and heated to 100 ° C. with stirring to obtain an alcoholate solution. Prepared. Meanwhile, 88 parts of diisopropyl succinate, 146.0 parts of 4-bromobenzonitrile and 7.6 parts of a benzonitrile compound of the formula (B-3-1) are added to a glass flask and heated to 90 ° C. with stirring. And dissolved to prepare solutions of these mixtures.
  • the solution was added in small portions. At this time, the rate of addition of the alkali metal salt of the diketopyrrolopyrrole compound at 75 ° C. while cooling so that the temperature of the mixture of methanol, acetic acid and water is always kept at ⁇ 5 ° C. or lower. was added in small portions over approximately 120 minutes. After addition of the alkali metal salt, red crystals were precipitated to form a red suspension. Subsequently, the obtained red suspension was washed with an ultrafiltration device at 5 ° C. and then filtered to obtain a red paste. This paste was re-dispersed in 3500 parts of methanol cooled to 0 ° C.
  • the diketopyrrolopyrrole compound aqueous paste obtained by filtering off with an ultrafiltration machine was dried at 80 ° C. for 24 hours and pulverized to obtain a diketopyrrolopyrrole pigment composition 145.8. Got a part.
  • the content of the specific hetero diketopyrrolopyrrole pigment B represented by the formula (1) was quantitatively analyzed using HPLC.
  • the mass ratio of the specific hetero diketopyrrolopyrrole pigment B represented by the formula was 94.5: 5.5.
  • Example 19 (Production of Pigment Composition 19 (R-19)) To a stainless steel reaction vessel equipped with a reflux tube, 200 parts of tert-amyl alcohol dehydrated with molecular sieves and 140 parts of sodium tert-amyl alkoxide are added in a nitrogen atmosphere, and heated to 100 ° C. with stirring to obtain an alcoholate solution. Prepared. Meanwhile, 88 parts of diisopropyl succinate, 138.3 parts of 4-bromobenzonitrile and 15.1 parts of a benzonitrile compound of the formula (B-3-1) are added to a glass flask and heated to 90 ° C. with stirring. And dissolved to prepare solutions of these mixtures.
  • the solution was added in small portions. At this time, the rate of addition of the alkali metal salt of the diketopyrrolopyrrole compound at 75 ° C. while cooling so that the temperature of the mixture of methanol, acetic acid and water is always kept at ⁇ 5 ° C. or lower. was added in small portions over approximately 120 minutes. After addition of the alkali metal salt, red crystals were precipitated to form a red suspension. Subsequently, the obtained red suspension was washed with an ultrafiltration device at 5 ° C. and then filtered to obtain a red paste. This paste was re-dispersed in 3500 parts of methanol cooled to 0 ° C.
  • the diketopyrrolopyrrole compound aqueous paste obtained by filtering off with an ultrafiltration machine was dried at 80 ° C. for 24 hours and pulverized to obtain a diketopyrrolopyrrole pigment composition 145.8. Got a part.
  • the content of the specific hetero diketopyrrolopyrrole pigment B represented by the formula (1) was quantitatively analyzed using HPLC.
  • the mass ratio of the specific hetero diketopyrrolopyrrole pigment B represented by the formula (8) was 88.9: 11.1.
  • Pigment Composition 20 (R-20) 100.0 parts of brominated diketopyrrolopyrrole pigment of formula (1), 1000 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 10 hours. Next, the kneaded mixture is put into warm water, stirred for 1 hour while heating to about 80 ° C. to form a slurry, filtered and washed with water to remove salt and diethylene glycol, and then dried at 80 ° C. for one day and pulverized. As a result, 96.6 parts of pigment composition 20 (R-20), which is a diketopyrrolopyrrole pigment composition, was obtained. The average primary particle size was 38.9 nm.
  • pigment composition 21 which is a diketopyrrolopyrrole pigment composition.
  • the average primary particle size was 28.4 nm.
  • pigment composition 22 which is a diketopyrrolopyrrole pigment composition.
  • the average primary particle size was 35.4 nm.
  • Pigment Composition 23 (R-23)) 80.0 parts of the specific heterodiketopyrrolopyrrole pigment B of the formula (B-2-1), 1000 parts of sodium chloride, and 110 parts of diethylene glycol are charged into a 1 gallon kneader (manufactured by Inoue Seisakusho) at 10 ° C. Kneaded for hours. Next, the kneaded mixture is put into warm water, stirred for 1 hour while heating to about 80 ° C. to form a slurry, filtered and washed with water to remove salt and diethylene glycol, and then dried at 80 ° C. for one day and pulverized. As a result, 76.8 parts of pigment composition 23 (R-23) which is a diketopyrrolopyrrole pigment composition was obtained. The average primary particle size was 39.4 nm.
  • pigment composition 24 which is a diketopyrrolopyrrole pigment composition.
  • the average primary particle size was 27.3 nm.
  • pigment composition 26 which is a diketopyrrolopyrrole pigment composition.
  • the average primary particle size was 31.4 nm.
  • dianthraquinone pigment 1 (Production of dianthraquinone pigment 1 (PR177-1)) 90 parts of a dianthraquinone pigment (CI Pigment Red177), 900 parts of sodium chloride, and 110 parts of diethylene glycol were charged into a stainless gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 10 hours. Next, the kneaded mixture is put into warm water, stirred for 1 hour while heating to about 80 ° C. to form a slurry, filtered and washed with water to remove salt and diethylene glycol, and then dried at 80 ° C. for one day and pulverized. As a result, 85.0 parts of dianthraquinone pigment 1 (PR177-1) were obtained. The average primary particle size was 38.2 nm.
  • azo pigment 1 (Production of azo pigment 1 (PY150-1)) 90 parts of an azo pigment (CI Pigment Yellow 150), 900 parts of sodium chloride and 110 parts of diethylene glycol were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 10 hours. Next, the kneaded mixture is put into warm water, stirred for 1 hour while heating to about 80 ° C. to form a slurry, filtered and washed with water to remove salt and diethylene glycol, and then dried at 80 ° C. for one day and pulverized. As a result, 85.0 parts of azo pigment 1 (PY150-1) were obtained. The average primary particle size was 26.2 nm.
  • an acrylic resin solution 2 was prepared.
  • the weight average molecular weight (Mw) was 18000.
  • the weight average molecular weight of the acrylic resin is a polystyrene equivalent weight average molecular weight measured by GPC (gel permeation chromatography).
  • Example 20 (Preparation of colored composition 1 (RP-1)) A mixture having the following composition is uniformly stirred and mixed, dispersed with Picomill (manufactured by Asada Tekko Co., Ltd.) for 8 hours using zirconia beads having a diameter of 0.1 mm, filtered through a 5 ⁇ m filter, and colored composition 1 (RP-1) was produced.
  • Diketopyrrolopyrrole pigment composition 1 (R-1) 11.0 parts
  • Dye derivative (14-1) 1.0 part
  • Acrylic resin solution 1 40.0 parts
  • Example 39 (Preparation of colored composition 20 (RP-20)) The mixture having the composition shown below was stirred and mixed uniformly, dispersed with picomil for 8 hours using zirconia beads having a diameter of 0.1 mm, filtered through a 5 ⁇ m filter, and colored composition 20 (RP-20) was obtained.
  • Diketopyrrolopyrrole pigment composition 19 (R-19) 11.0 parts
  • Dye derivative (6-3) 1.0 part
  • Resin type dispersant (“BYK161" (30% solution) manufactured by BYK Chemie) 6.0 parts
  • Example 40 (Preparation of colored composition 21 (RP-21)) The mixture having the composition shown below was uniformly stirred and mixed, dispersed with picomil for 8 hours using zirconia beads having a diameter of 0.1 mm, filtered through a 5 ⁇ m filter, and colored composition 21 (RP-21) was obtained.
  • Diketopyrrolopyrrole pigment composition 19 (R-19) 12.0 parts Resin-type dispersant (“Ajisper PB821” manufactured by Ajinomoto Fine Techno Co., Ltd.) 3.6 parts Acrylic resin solution 1 23.0 parts Propylene glycol monomethyl ether acetate 61.4 parts
  • Coloring composition 1 38.2 parts Coloring composition 29 (RP-29) 3.8 parts Acrylic resin solution 2 13.2 parts Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 2.8 parts Photopolymerization initiator ("Irgacure 907” manufactured by Ciba Japan Co., Ltd.) 2.0 parts Sensitizer (“EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts Ethylene glycol monomethyl ether acetate 39.6 Part
  • Example 42 to 61 (Preparation of photosensitive coloring compositions 2 to 21 (RR-2 to 21)) Coloring composition 1 (RP-1) was changed to coloring compositions 2 to 21 (RP-2 to 21), and coloring compositions 2 to 21 (RP-2 to 21) and coloring composition 29 (RP-29) ) was changed in the same manner as in Example 41 except that the ratio was changed within 42 parts of the total amount of the colored composition.
  • Photosensitive colored compositions 2 to 21 (RP-2 to 21) were prepared.
  • the ratio of composition 29 (RP-29) was changed.
  • Coloring composition 1 was changed to coloring compositions 22-25, 27, 28 (RP-22-25, 27, 28), and further colored compositions 22-25, 27, 28 (RP-22) 25, 27, 28) and the colored composition 29 (RP-29), except that the ratio of the colored composition 29 is changed within 42 parts of the colored composition.
  • 25 27, 28 (RR-22 to 25, 27, 28) were prepared.
  • 25, 27, 28) and the ratio of the colored composition 29 (RP-29) were changed.
  • the light emitted from the backlight unit for liquid crystal display is polarized through the polarizing plate, passes through the dried coating film of the colored composition applied on the glass substrate, and reaches the polarizing plate. If the polarizing planes of the polarizing plate and the polarizing plate are parallel, light is transmitted through the polarizing plate, but if the polarizing plane is perpendicular, the light is blocked by the polarizing plate.
  • a color luminance meter (“BM-5A” manufactured by Topcon Corporation) was used as the luminance meter, and a polarizing plate (“NPF-G1220DUN” manufactured by Nitto Denko Corporation) was used as the polarizing plate.
  • NPF-G1220DUN manufactured by Nitto Denko Corporation
  • a black mask with a 1 cm square hole was applied to the measurement portion in order to block unnecessary light.
  • contrast ratio measurement a red coating film obtained by the same method as that used for color characteristic evaluation was used.
  • Example 43 In the comparison between Example 43 and Reference Example 21, a photosensitive coloring composition using a diketopyrrolopyrrole pigment composition containing a brominated diketopyrrolopyrrole pigment and a specific hetero diketopyrrolopyrrole pigment B is conventionally known.
  • the result was higher brightness and higher contrast than the photosensitive coloring composition containing Pigment Red 254, and no problem with crystal precipitation.
  • the brominated diketopyrrolopyrrole pigment which does not contain the specific hetero diketopyrrolopyrrole pigment B of Reference Example 15 is excellent in lightness, it was found that the contrast was low and crystal precipitation could not be suppressed.
  • Example 42 Examples 45 to 47, and Examples 49 to 53, it was also confirmed that the effect of using the specific hetero diketopyrrolopyrrole pigment B depends on the type. .
  • Example 42 and Example 56 the pigment composition produced by the succinic acid diester co-synthesis method, the brominated diketopyrrolopyrrole pigment and the specific hetero diketopyrrolopyrrole pigment B were synthesized separately and mixed during the salt milling treatment. It was found that the same effect can be obtained with the pigment composition produced in this way. The same effect could be confirmed in the comparison between Example 43 and Example 59.
  • Green coloring composition 1 (GP-1)
  • the mixture having the composition shown below was uniformly stirred and mixed, dispersed with picomil for 8 hours using zirconia beads having a diameter of 0.1 mm, filtered through a 5 ⁇ m filter, and green colored composition 1 (GP-1) was made.
  • Green pigment (CI Pigment Green 36) 6.8 parts
  • Yellow pigment (CI Pigment Yellow 150) 5.2 parts
  • Resin-type dispersant ("EFKA4300" manufactured by Ciba Japan) 1.0 parts
  • Acrylic resin Solution 1 35.0 parts Propylene glycol monomethyl ether acetate 52.0 parts
  • Green coloring composition 1 (GP-1)) A mixture having the following composition was stirred and mixed to be uniform, and then filtered through a 1 ⁇ m filter to prepare green photosensitive coloring composition 1 (GR-1).
  • Green coloring composition 1 (GP-1) 42.0 parts Acrylic resin solution 2 13.2 parts Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 2.8 parts Photopolymerization initiator (Ciba Japan) "Irgacure 907" manufactured by the company) 2.0 parts Sensitizer ("EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts 39.6 parts ethylene glycol monomethyl ether acetate
  • Blue coloring composition 1 (BP-1) 34.0 parts Acrylic resin solution 2 15.2 parts Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 3.3 parts Photopolymerization initiator (Ciba Japan) "Irgacure 907” manufactured by the company) 2.0 parts Sensitizer ("EAB-F” manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts 45.1 parts ethylene glycol monomethyl ether acetate
  • a colored coating was formed.
  • the film was irradiated with ultraviolet rays of 300 mJ / cm 2 using a super high pressure mercury lamp through a photomask.
  • spray development was performed with an alkaline developer composed of a 0.2% by weight aqueous sodium carbonate solution to remove unexposed portions, followed by washing with ion-exchanged water.
  • the substrate was heated at 230 ° C. for 20 minutes to obtain a red filter segment. Formed.
  • Example C In Example C, “parts” and “%” represent “parts by weight” and “% by weight”, respectively.
  • the specific surface area of the pigment, the primary particle diameter of the pigment, the weight average molecular weight (Mw) of the resin, the acid value of the resin, and the contrast ratio (CR) of the coating film are as follows.
  • the specific surface area of the pigment particles was determined by the BET method using nitrogen adsorption.
  • an automatic vapor adsorption amount measuring device (“BELSORP18” manufactured by Nippon Bell Co., Ltd.) was used.
  • the average primary particle diameter of the pigment was measured by a method of directly measuring the primary particle size from an electron micrograph. Specifically, the minor axis diameter and major axis diameter of the primary particles of each pigment were measured, and the average was taken as the particle diameter of the pigment particles. Next, for 100 or more pigment particles, the volume (weight) of each particle was obtained by approximating the obtained particle size cube, and the volume average particle size was defined as the average primary particle size.
  • the electron microscope used was a transmission type (TEM).
  • Weight average molecular weight of resin It is a weight average molecular weight (Mw) in terms of polystyrene measured using a TSKgel column (manufactured by Tosoh Corporation) and using GPC (manufactured by Tosoh Corporation, HLC-8120GPC) equipped with an RI detector using THF as a developing solvent.
  • the light emitted from the backlight unit for liquid crystal display is polarized through the polarizing plate, passes through the dried coating film of the colored composition applied on the glass substrate, and reaches the polarizing plate. If the polarizing planes of the polarizing plate and the polarizing plate are parallel, light is transmitted through the polarizing plate, but if the polarizing plane is perpendicular, the light is blocked by the polarizing plate. However, when the light polarized by the polarizing plate passes through the dried coating film of the colored composition, scattering by the pigment particles occurs, and when a part of the polarization plane is displaced, the polarized light is polarized when the polarizing plate is parallel.
  • the binder resin (B) solutions used in the examples and reference examples the pigment (A1) represented by the formula (1), the refined pigment, and the method for producing the pigment dispersion will be described.
  • ⁇ Method for producing pigment (A1) represented by formula (1)> First, in a stainless steel reaction vessel equipped with a reflux tube, 200 parts of tert-amyl alcohol dehydrated with molecular sieves and 140 parts of sodium tert-amyl alkoxide were added in a nitrogen atmosphere and heated to 100 ° C. with stirring to produce alcoholate. A solution was prepared. On the other hand, 88 parts of diisopropyl succinate and 153.6 parts of 4-bromobenzonitrile were added to a glass flask and dissolved by heating to 90 ° C. with stirring to prepare a solution of these mixtures. A heated solution of this mixture was slowly dropped into the alcoholate solution heated to 100 ° C. at a constant rate over 2 hours with vigorous stirring.
  • the rate of addition of the alkali metal salt of the diketopyrrolopyrrole compound at 75 ° C. while cooling so that the temperature of the mixture of methanol, acetic acid and water is always kept at ⁇ 5 ° C. or lower. was added in small portions over approximately 120 minutes.
  • red crystals were precipitated to form a red suspension.
  • the obtained red suspension was washed with an ultrafiltration device at 5 ° C. and then filtered to obtain a red paste. This paste was re-dispersed in 3500 parts of methanol cooled to 0 ° C. to make a suspension with a methanol concentration of about 90%, and stirred at 5 ° C.
  • the water paste of the diketopyrrolopyrrole compound obtained by filtration with an ultrafiltration machine was dried at 80 ° C. for 24 hours, and pulverized with the pigment (A1) represented by the formula (1). 150.8 parts of a brominated diketopyrrolopyrrole pigment 1 were obtained.
  • Brominated diketopyrrolopyrrole pigment (A1-1) Brominated diketopyrrolopyrrole pigment 1 was charged in 100.0 parts, 1000 parts of sodium chloride, and 120 parts of diethylene glycol, and a 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 2 hours. Next, the kneaded mixture is put into warm water, stirred for 1 hour while heating to about 80 ° C. to form a slurry, filtered and washed with water to remove salt and diethylene glycol, and then dried at 80 ° C. for one day and pulverized.
  • a 1 gallon kneader manufactured by Inoue Seisakusho
  • Brominated diketopyrrolopyrrole pigment (A1-2) Brominated diketopyrrolopyrrole pigment 1 (100.0 parts), sodium chloride (1000 parts) and diethylene glycol (120 parts) were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 4 hours. Next, the kneaded mixture is put into warm water, stirred for 1 hour while heating to about 80 ° C. to form a slurry, filtered and washed with water to remove salt and diethylene glycol, and then dried at 80 ° C. for one day and pulverized. As a result, 96.6 parts of brominated diketopyrrolopyrrole pigment (A1-2) was obtained. The average primary particle diameter was 55 nm, and the specific surface area was 45 m 2 / g.
  • brominated diketopyrrolopyrrole pigment (A1-3) 100.0 parts of brominated diketopyrrolopyrrole pigment 1, 1000 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 8 hours. Next, the kneaded mixture is put into warm water, stirred for 1 hour while heating to about 80 ° C. to form a slurry, filtered and washed with water to remove salt and diethylene glycol, and then dried at 80 ° C. for one day and pulverized. As a result, 96.5 parts of brominated diketopyrrolopyrrole pigment (A1-3) was obtained. The average primary particle diameter was 38 nm, and the specific surface area was 80 m 2 / g.
  • brominated diketopyrrolopyrrole pigment (A1-4) 100.0 parts of brominated diketopyrrolopyrrole pigment 1, 1000 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 12 hours. Next, the kneaded mixture is put into warm water, stirred for 1 hour while heating to about 80 ° C. to form a slurry, filtered and washed with water to remove salt and diethylene glycol, and then dried at 80 ° C. for one day and pulverized. As a result, 96.2 parts of a brominated diketopyrrolopyrrole pigment (A1-4) was obtained. The average primary particle diameter was 30 nm, and the specific surface area was 120 m 2 / g.
  • Brominated diketopyrrolopyrrole pigment (A1-5) Brominated diketopyrrolopyrrole pigment 1 (100.0 parts), sodium chloride (1000 parts) and diethylene glycol (120 parts) were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 24 hours. Next, the kneaded mixture is put into warm water, stirred for 1 hour while heating to about 80 ° C. to form a slurry, filtered and washed with water to remove salt and diethylene glycol, and then dried at 80 ° C. for one day and pulverized. As a result, 96.2 parts of brominated diketopyrrolopyrrole pigment (A1-5) was obtained. The average primary particle diameter was 19 nm, and the specific surface area was 180 m 2 / g.
  • Brominated diketopyrrolopyrrole pigment (A1-6) Brominated diketopyrrolopyrrole pigment 1 (100.0 parts), sodium chloride (1000 parts) and diethylene glycol (120 parts) were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 48 hours. Next, the kneaded mixture is put into warm water, stirred for 1 hour while heating to about 80 ° C. to form a slurry, filtered and washed with water to remove salt and diethylene glycol, and then dried at 80 ° C. for one day and pulverized. As a result, 96.2 parts of brominated diketopyrrolopyrrole pigment (A1-6) was obtained. The average primary particle diameter was 9 nm, and the specific surface area was 270 m 2 / g.
  • Pigment dispersion (P-5) A pigment dispersion (P-5) was prepared in the same manner as the red pigment dispersion (P-1) except that the brominated diketopyrrolopyrrole pigment (A1-1) was changed to a brominated diketopyrrolopyrrole pigment (A1-5). )
  • a red pigment dispersion (P-6) was prepared in the same manner as the red pigment dispersion (P-1) except that the brominated diketopyrrolopyrrole pigment (A1-1) was changed to a brominated diketopyrrolopyrrole pigment (A1-6). 6) was obtained.
  • Pigment dispersion (P-7) Red pigment except that brominated diketopyrrolopyrrole pigment (A1-1) is changed to chlorinated diketopyrrolopyrrole pigment (CI Pigment Red 254; “Irga Four Red B-CF” manufactured by Ciba Japan) A red pigment dispersion (P-7) was obtained in the same manner as dispersion (P-1).
  • Pigment dispersion (P-8) After the mixture having the following composition is uniformly stirred and mixed, it is dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) for 5 hours using zirconia beads having a diameter of 1 mm, and then filtered through a 5 ⁇ m filter. A pigment dispersion (P-8) was obtained.
  • Eiger mill Mini Model M-250 MKII manufactured by Eiger Japan
  • Brominated diketopyrrolopyrrole pigment (A1-3) 6.82 parts Anthraquinone pigment (CI Pigment Red 177) 1.08 parts (Chromotal Red A2B manufactured by Ciba Japan) Nickel azo complex pigment (CI Pigment Yellow 150) 0.88 parts ("E4GN” manufactured by LANXESS) Acid resin type pigment dispersant 1.74 parts (“Solsperse 21000” manufactured by Nippon Lubrizol) Pigment derivative 1 2.05 parts Acrylic resin solution 1 5.83 parts Cyclohexanone 81.60 parts
  • Pigment dispersion (P-9 to 20) The pigment dispersions (P-9 to P-9) were the same as the pigment dispersions (P-8) except that the types and blending amounts of the pigments, pigment derivatives, and resin-type pigment dispersants shown in Table C-2 were changed. 20) was obtained.
  • Example 1 (Red coloring composition (DR-1)) A mixture having the following composition was stirred and mixed uniformly, and then filtered through a 5 ⁇ m filter to obtain a red colored composition (DR-1). Red pigment dispersion (P-1) 40.5 parts Alkali-soluble photosensitive resin (B1-1) 8.6 parts Cyclohexanone 50.9 parts
  • OSP-SP200 microspectrophotometer
  • the substrate obtained by color characteristic and contrast ratio (CR) evaluation was further subjected to heat treatment at 240 ° C. for 60 minutes twice.
  • the coating film surface of the coated substrate after the heat treatment was observed with an optical microscope, and the presence or absence of crystal precipitation was determined according to the following criteria.
  • ⁇ and ⁇ are good without crystal precipitation
  • ⁇ is a level where there is crystal precipitation but no problem in use
  • ⁇ corresponds to a state where it cannot be used due to crystal precipitation.
  • the coloring composition for a color filter containing the pigment (A1) represented by the formula (1) and the alkali-soluble photosensitive resin (B1) has a high brightness and a high contrast ratio, and the diketopyrrolopyrrole can be obtained by the heating process. Good results were obtained that no crystal precipitation of the pigments occurred.
  • Photopolymerization initiator D1 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one (“Irgacure 907” manufactured by Ciba Japan)
  • Photopolymerization initiator D2 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] -1-butanone (“Irgacure 379” manufactured by Ciba Japan) ”)
  • Photopolymerization initiator D3 ethane-1-one, 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl], 1- (O-acetyloxime) (“Irgacure OXE02" manufactured by Ciba Japan)
  • Photopolymerization initiator D4 2,2′-bis (o-
  • Sensitizer E1 2,4-diethylthioxanthone (“Kayacure DETX-S” manufactured by Nippon Kayaku Co., Ltd.)
  • Sensitizer E2 4,4′-bis (diethylamino) benzophenone (“EAB-F” manufactured by Hodogaya Chemical Co., Ltd.)
  • Photopolymerizable compound Dipentaerythritol hexaacrylate (“Aronix M-402” manufactured by Toagosei Co., Ltd.)
  • Multifunctional thiol F1 Trimethylolethane tris (3-mercaptobutyrate) ("TEMB” manufactured by Showa Denko KK)
  • Multifunctional thiol F2 trimethylolpropane tri (3-mercaptobutyrate) ("TPMB” manufactured by Showa Denko KK)
  • Multifunctional thiol F3 pentaerythritol tetrakis (3-mercaptopropionate) (“PEMP” manufactured by Sakai Chemical Industry Co., Ltd.)
  • UV absorber G1 2- [4-[(2-hydroxy-3- (dodecyl and tridecyl) oxypropyl) oxy] -2-hydroxyphenyl] -4,6-bis (2,4-dimethylphenyl) -1 , 3,5-triazine ("TINUVIN400" manufactured by Ciba Japan)
  • UV absorber G2 2- (2H-benzotriazol-2-yl) -4,6-bis (1-methyl-1-phenylethyl) phenol (“TINUVIN900” manufactured by Ciba Japan)
  • Polymerization inhibitor H1 N-nitrosophenylhydroxylamine aluminum salt (“Q-1301” manufactured by Wako Pure Chemical Industries, Ltd.)
  • Polymerization inhibitor H2 Methylhydroquinone (“MH” manufactured by Seiko Chemical Co., Ltd.)
  • Storage stabilizer J1 2,6-bis (1,1-dimethylethyl) -4-methylphenol (“BHT” manufactured by Honshu Chemical Industry Co., Ltd.)
  • Storage stabilizer J2 Triphenylphosphine (“TPP” manufactured by Hokuko Chemical Co., Ltd.)
  • OSP-SP200 microspectrophotometer
  • the substrate obtained by color characteristics and contrast ratio (CR) evaluation was further heated at 260 ° C. for 1 hour and allowed to cool.
  • the coating film surface of the coated substrate after the heat treatment was observed with an optical microscope, and the presence or absence of crystal precipitation was determined according to the following criteria.
  • ⁇ is very good without crystal precipitation
  • ⁇ is a good level with some crystal precipitation
  • ⁇ is a level with no crystal precipitation
  • ⁇ is used by crystal precipitation. It corresponds to a state where it cannot.
  • A The number of crystals is 1 or more and less than 10.
  • ⁇ The number of crystals is 10 or more and less than 100.
  • X The number of crystals is 100 or more.
  • the solvent was removed by heating at 70 ° C. for 20 minutes in a clean oven to form a coating film of about 2 ⁇ m. Obtained.
  • the substrate was cooled to room temperature, and then exposed to ultraviolet rays through a photomask having a stripe pattern of 100 ⁇ m width (pitch 200 ⁇ m) and 25 ⁇ m width (pitch 50 ⁇ m) using an ultrahigh pressure mercury lamp.
  • this substrate was spray-developed using a sodium carbonate aqueous solution at 23 ° C., washed with ion-exchanged water, air-dried, and heated at 230 ° C. for 330 minutes in a clean oven.
  • the spray development was performed in the shortest time during which a pattern can be formed without any development remaining on the coating film of each photosensitive coloring composition, and this was set as an appropriate development time.
  • the film thickness of the coating film was determined using Dektak 3030 (manufactured by Nippon Vacuum Technology Co., Ltd.).
  • Linearity evaluation The pattern in the 100 ⁇ m photomask portion of the filter segment formed by the above method was evaluated by observing with an optical microscope. The rank of evaluation is as follows. ⁇ : Good linearity ⁇ : Partially poor linearity ⁇ : Poor linearity
  • the color filter coloring composition containing the pigment (A1) and the photosensitive resin (B1) represented by the formula (1) obtained high-level evaluation results in all evaluations.
  • the photosensitive coloring composition (RR-1) was coated on a 100 mm ⁇ 100 mm glass substrate with a die coater to a thickness of about 2 ⁇ m, and the solvent was removed and dried in an oven at 70 ° C. for 20 minutes. Subsequently, stripe pattern exposure was performed with ultraviolet rays using an exposure apparatus. The exposure amount was 100 mJ / cm 2 . Furthermore, after spray development with a developer composed of an aqueous sodium carbonate solution to remove unexposed portions, the substrate is washed with ion-exchanged water, and this substrate is heated at 230 ° C. for 30 minutes to form a red filter segment having a line width of about 50 ⁇ m. did. Next, in the same manner, a green filter segment is formed using the green photosensitive coloring composition next to the red filter segment, and then a blue filter segment is formed using the blue photosensitive coloring composition. A color filter comprising a color filter segment was obtained.
  • Example D In Example D, “parts” and “%” represent “parts by weight” and “% by weight”, respectively.
  • the specific surface area of the pigment, the primary particle diameter of the pigment, the weight average molecular weight (Mw) of the resin, the acid value of the resin, and the contrast ratio (CR) of the coating film are as follows.
  • the specific surface area of the pigment particles was determined by the BET method using nitrogen adsorption.
  • an automatic vapor adsorption amount measuring device (“BELSORP18” manufactured by Nippon Bell Co., Ltd.) was used.
  • the average primary particle diameter of the pigment was measured by a method of directly measuring the primary particle size from an electron micrograph. Specifically, the minor axis diameter and major axis diameter of the primary particles of each pigment were measured, and the average was taken as the particle diameter of the pigment particles. Next, for 100 or more pigment particles, the volume (weight) of each particle was obtained by approximating the obtained particle size cube, and the volume average particle size was defined as the average primary particle size.
  • the electron microscope used was a transmission type (TEM).
  • Weight average molecular weight of resin It is a weight average molecular weight (Mw) in terms of polystyrene measured by using TSKgel column (manufactured by Tosoh Corporation) and using GPC (manufactured by Tosoh Corporation, HLC-8120GPC) equipped with an RI detector using THF as a developing solvent.
  • the light emitted from the backlight unit for liquid crystal display is polarized through the polarizing plate, passes through the dried coating film of the colored composition applied on the glass substrate, and reaches the polarizing plate. If the polarizing planes of the polarizing plate and the polarizing plate are parallel, light is transmitted through the polarizing plate, but if the polarizing plane is perpendicular, the light is blocked by the polarizing plate. However, when the light polarized by the polarizing plate passes through the dried coating film of the colored composition, scattering by the pigment particles occurs, and when a part of the polarization plane is displaced, the polarized light is polarized when the polarizing plate is parallel.
  • the binder resin (B) solutions used in the examples and reference examples the pigment (A1) represented by the formula (1), the refined pigment, and the method for producing the pigment dispersion will be described.
  • Step 1 Polymerization of resin main chain
  • PGMAC propylene glycol monomethyl ether acetate
  • Step 2 Polymerization to epoxy group
  • the inside of the flask was purged with air, and 17.0 parts of acrylic acid and 0.3 part of trisdimethylaminomethylphenol and 0.3 part of hydroquinone as the catalyst required for the polymerization of the precursor at this stage were charged at 120 ° C. Reaction was performed for 5 hours, and the resin solution whose weight average molecular weight is about 12000 (measurement by GPC) was obtained.
  • the added acrylic acid is ester-bonded to the end of the epoxy group of the glycidyl methacrylate structural unit, so that no carboxyl group is generated in the resin structure.
  • Step 3 Polymerization to hydroxyl group
  • 30.4 parts of tetrahydrophthalic anhydride and 0.5 parts of triethylamine as a catalyst required for polymerization of the precursor at this stage were added and reacted at 120 ° C. for 4 hours.
  • the added tetrahydrophthalic anhydride one of two carboxyl groups generated by cleavage of the carboxylic anhydride moiety is ester-bonded to a hydroxyl group in the resin structure, and the other produces a carboxyl group terminal.
  • Step 4 Adjustment of nonvolatile content
  • Propylene glycol monomethyl ether acetate was added so that the nonvolatile content was 40% to obtain a resin solution (B1-1).
  • the weight ratio of the structural unit in the resin solution (B1-1) is as follows: tetrahydrophthalic anhydride as the structural unit (Db1); 21.7% by weight; styrene as the structural unit (Db2); 11.6% by weight;
  • the structural unit (Db3) is dicyclopentanyl methacrylate; 29.3% by weight, and the other structural unit is glycidyl methacrylate and the total of acrylic acid ester-bonded to the glycidyl terminal; 37.4% by weight.
  • the reaction was further carried out at 100 ° C. for 3 hours, and then 1.0 part of azobisisobutyronitrile dissolved in 50 parts of cyclohexanone was added, and the reaction was further continued at 100 ° C. for 1 hour.
  • the inside of the container was replaced with air, 0.5 parts of trisdimethylaminophenol and 0.1 part of hydroquinone were added to 9.3 parts of acrylic acid (equivalent of epoxy group), and 6 parts at 120 ° C.
  • the reaction was continued for a period of time, and the reaction was terminated when the acid value of the solid content reached 0.5 to obtain an acrylic resin solution.
  • 19.5 parts of tetrahydrophthalic anhydride (equivalent of generated hydroxyl group) and 0.5 parts of triethylamine were added and reacted at 120 ° C. for 3.5 hours to obtain an acrylic resin solution.
  • the precursors corresponding to the structural units (Db1) to (Db3) and other structural units were replaced according to Table D-1.
  • all the precursors are mixed and only the production steps 1 and 4 are carried out.
  • GMA-AA or GMA-MAA is present in the table and THPA is present, first, GMA and GMA-AA or GMA in the structural units (Db2), (Db3) and other structural units -Precursor excluding MAA is mixed to carry out production stage 1, then GMA epoxy equivalent of AA or MAA is added as precursor to carry out production stage 2 and further THPA is added as precursor.
  • Steps 3 and 4 of the manufacturing are performed.
  • GMA-AA or GMA-MAA is present in the table and THPA is not present
  • GMA, GMA-AA or GMA- in the structural units (Db1) to (Db3) and other structural units are used.
  • Precursor excluding MAA is mixed to carry out stage 1 of production, then epoxy equivalent AA or MAA of GMA is added as a precursor to carry out stage 2 of production, and stage 4 is carried out.
  • the number of catalyst parts required for each stage is mixed in proportion to the total number of precursors mixed in each stage.
  • composition and weight ratio of the obtained resin solutions (B1-1 to 15) and resin solutions (B2-1 to 4) are shown in Table D-1.
  • the value in parentheses represents the weight ratio (% by weight) of the constituent unit in the resin solid content.
  • the solution was added in small portions. At this time, the rate of addition of the alkali metal salt of the diketopyrrolopyrrole compound at 75 ° C. while cooling so that the temperature of the mixture of methanol, acetic acid and water is always kept at ⁇ 5 ° C. or lower. was added in small portions over approximately 120 minutes. After addition of the alkali metal salt, red crystals were precipitated to form a red suspension. Subsequently, the obtained red suspension was washed with an ultrafiltration device at 5 ° C. and then filtered to obtain a red paste. This paste was re-dispersed in 3500 parts of methanol cooled to 0 ° C.
  • the obtained brominated diketopyrrolopyrrole pigment (100.0 parts), sodium chloride (1000 parts), and diethylene glycol (120 parts) were charged into a stainless gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 8 hours.
  • the kneaded mixture is put into warm water, stirred for 1 hour while heating to about 80 ° C. to form a slurry, filtered and washed with water to remove salt and diethylene glycol, and then dried at 80 ° C. for one day and pulverized.
  • A1-1 represented by the formula (1)
  • Pigment dispersion (P-1) After the mixture having the following composition is uniformly stirred and mixed, it is dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) for 5 hours using zirconia beads having a diameter of 1 mm, and then filtered through a 5 ⁇ m filter. A pigment dispersion (P-1) was obtained.
  • Eiger mill Mini Model M-250 MKII manufactured by Eiger Japan
  • a pigment dispersion (P-1) was obtained.
  • Brominated diketopyrrolopyrrole pigment (A1-1) 8.78 parts Acidic resin type pigment dispersant 1.74 parts (BYK-111 manufactured by Big Chemie Japan) Pigment derivative 1 2.05 parts Resin solution (B2-5) 5.83 parts Cyclohexanone 81.60 parts
  • Pigment dispersion (P-2) Pigment dispersion except that brominated diketopyrrolopyrrole pigment (A1-1) was changed to chlorinated diketopyrrolopyrrole pigment (CI Pigment Red 254; “Irga Four Red B-CF” manufactured by Ciba Japan) A pigment dispersion (P-2) was obtained in the same manner as for the body (P-1).
  • Pigment dispersion (P-3) After the mixture having the following composition is uniformly stirred and mixed, it is dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) for 5 hours using zirconia beads having a diameter of 1 mm, and then filtered through a 5 ⁇ m filter. A pigment dispersion (P-3) was obtained.
  • Brominated diketopyrrolopyrrole pigment (A1-1) 6.82 parts Anthraquinone pigment (CI Pigment Red177) 1.08 parts (“Chromotal Red A2B” manufactured by Ciba Japan) Nickel azo complex pigment (CI Pigment Yellow 150) 0.88 parts ("E4GN” manufactured by LANXESS) Acidic resin type pigment dispersant 1.74 parts (Solsperse 21000 by Nippon Lubrizol) Pigment derivative 1 2.05 parts Resin solution (B2-5) 5.83 parts Cyclohexanone 81.60 parts
  • Pigment dispersion (P-4 to 10) The pigment dispersions (P-4 to P-4) were the same as the pigment dispersions (P-3) except that the types and blending amounts of the pigments, pigment derivatives, and resin-type pigment dispersants shown in Table D-2 were changed. 11) was obtained.
  • Example 1 (Red coloring composition (DR-1)) A mixture having the following composition was stirred and mixed uniformly, and then filtered through a 5 ⁇ m filter to obtain a red colored composition (DR-1). Red pigment dispersion (P-R1) 40.5 parts Resin solution (B1-1) 8.6 parts Cyclohexanone 50.9 parts
  • Red coloring composition (DR-2 to 7) Red colored compositions (DR-2 to 7) are obtained in the same manner as the red colored composition (DR-1) except that the resin solution (B1-1) is changed to the resin solution shown in Table D-2. It was.
  • Red coloring composition (DR-8) A red colored composition (DR-8) was obtained in the same manner as the red colored composition (DR-1) except that the red pigment dispersion (P-R1) was changed to a red pigment dispersion (P-R2). It was.
  • OSP-SP200 microspectrophotometer
  • the substrate obtained by color characteristic and contrast ratio (CR) evaluation was further subjected to heat treatment at 240 ° C. for 60 minutes twice.
  • the coating film surface of the coated substrate after the heat treatment was observed with an optical microscope, and the presence or absence of crystal precipitation was determined according to the following criteria.
  • ⁇ and ⁇ are good without crystal precipitation
  • ⁇ is a level where there is crystal precipitation but no problem in use
  • ⁇ corresponds to a state where it cannot be used due to crystal precipitation.
  • the color composition for color filter comprising the pigment (A1) represented by the formula (1) and the resin (DB1) having the structural units (Db1) to (Db3) has high brightness and high contrast.
  • the results show that the diketopyrrolopyrrole pigment does not crystallize even in the heating step.
  • Photopolymerization initiator D1 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one (“Irgacure 907” manufactured by Ciba Japan)
  • Photopolymerization initiator D2 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] -1-butanone (“Irgacure 379” manufactured by Ciba Japan) ”)
  • Photopolymerization initiator D4 2,2′-bis (o-chlorophenyl) -4,5,4 ′, 5′-tetraphenyl-1,2′-biimid
  • Sensitizer E1 2,4-diethylthioxanthone (“Kayacure DETX-S” manufactured by Nippon Kayaku Co., Ltd.)
  • Sensitizer E2 4,4′-bis (diethylamino) benzophenone (“EAB-F” manufactured by Hodogaya Chemical Co., Ltd.)
  • Photopolymerizable compound C1 Dipentaerythritol hexaacrylate (“Aronix M-402” manufactured by Toagosei Co., Ltd.)
  • Multifunctional thiol F1 Trimethylolethane tris (3-mercaptobutyrate) ("TEMB” manufactured by Showa Denko KK)
  • Multifunctional thiol F2 trimethylolpropane tri (3-mercaptobutyrate) ("TPMB” manufactured by Showa Denko KK)
  • Multifunctional thiol F3 pentaerythritol tetrakis (3-mercaptopropionate) (“PEMP” manufactured by Sakai Chemical Industry Co., Ltd.)
  • UV absorber G1 2- [4-[(2-hydroxy-3- (dodecyl and tridecyl) oxypropyl) oxy] -2-hydroxyphenyl] -4,6-bis (2,4-dimethylphenyl) -1 , 3,5-triazine ("TINUVIN400" manufactured by Ciba Japan)
  • UV absorber G2 2- (2H-benzotriazol-2-yl) -4,6-bis (1-methyl-1-phenylethyl) phenol (“TINUVIN900” manufactured by Ciba Japan)
  • Storage stabilizer J1 2,6-bis (1,1-dimethylethyl) -4-methylphenol (“BHT” manufactured by Honshu Chemical Industry Co., Ltd.)
  • Storage stabilizer J2 Triphenylphosphine (“TPP” manufactured by Hokuko Chemical Co., Ltd.)
  • OSP-SP200 microspectrophotometer
  • the substrate obtained by color characteristics and contrast ratio (CR) evaluation was further heated at 260 ° C. for 1 hour and allowed to cool.
  • the coating film surface of the coated substrate after the heat treatment was observed with an optical microscope, and the presence or absence of crystal precipitation was determined according to the following criteria.
  • ⁇ is very good without crystal precipitation
  • ⁇ is a good level with some crystal precipitation
  • ⁇ is a level with no crystal precipitation
  • ⁇ is used by crystal precipitation. It corresponds to a state where it cannot.
  • A The number of crystals is 1 or more and less than 10.
  • ⁇ The number of crystals is 10 or more and less than 100.
  • X The number of crystals is 100 or more.
  • the solvent was removed by heating at 70 ° C. for 20 minutes in a clean oven to form a coating film of about 2 ⁇ m. Obtained.
  • the substrate was cooled to room temperature, and then exposed to ultraviolet rays through a photomask having a stripe pattern of 100 ⁇ m width (pitch 200 ⁇ m) and 25 ⁇ m width (pitch 50 ⁇ m) using an ultrahigh pressure mercury lamp.
  • this substrate was spray-developed using a sodium carbonate aqueous solution at 23 ° C., washed with ion-exchanged water, air-dried, and heated at 230 ° C. for 330 minutes in a clean oven.
  • the spray development was performed in the shortest time during which a pattern can be formed without any development remaining on the coating film of each photosensitive coloring composition, and this was set as an appropriate development time.
  • the film thickness of the coating film was determined using Dektak 3030 (manufactured by Nippon Vacuum Technology Co., Ltd.).
  • Linearity evaluation The pattern in the 100 ⁇ m photomask portion of the filter segment formed by the above method was evaluated by observing with an optical microscope. The rank of evaluation is as follows. ⁇ : Good linearity ⁇ : Partially poor linearity ⁇ : Poor linearity
  • the pattern in the 25 ⁇ m photomask portion of the filter segment formed by the above method was evaluated by observing with an optical microscope.
  • the rank of evaluation is as follows.
  • the poor resolution means that adjacent stripe patterns are connected or chipped.
  • the rank of evaluation is as follows. ⁇ : Good resolution and linearity ⁇ : Slightly inferior in linearity but good resolution ⁇ : Partially poor resolution ⁇ : Poor resolution
  • a coloring composition for a color filter comprising the pigment (A1) represented by the formula (1) and a resin (DB1) having structural units (Db1) to (Db3) Obtained high-level evaluation results in all evaluations.
  • the composition containing a large amount of the structural unit (Db1) of the resin (DB1) improves the contrast and stabilizes the stability over time.
  • the brightness and the chemical resistance are improved.
  • the composition containing a large amount of the structural unit (Db3) the effect of suppressing the crystal precipitation of the pigment and the effect of suppressing the resolution in the heating process tend to be recognized.
  • the structural unit satisfies a specific content ratio, a photosensitive colored composition having high performance can be obtained. By setting an appropriate constitutional unit ratio, it is possible to obtain a color filter segment with high performance and good balance.
  • the photopolymerization initiator (D) is a combination of any one of an acetophenone compound, a phosphine compound, an imidazole compound, and an oxime ester compound, the sensitivity, linearity, and resolution are better.
  • the photopolymerization initiator (D) is ethane-1-one, 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl], 1- (O-acetyloxime).
  • the photosensitive coloring composition was further excellent in development resistance. Furthermore, the photosensitive coloring composition containing polyfunctional thiol was more excellent in development resistance. Further, the photosensitive coloring composition further containing an ultraviolet absorber was superior in resolution. Further, the photosensitive coloring composition further containing a storage stabilizer was superior in stability over time.
  • the photosensitive coloring compositions of Reference Examples 3 to 9 have low brightness and contrast ratios, and all are satisfactory even in the evaluation of filter segments including pigment crystal precipitation and sensitivity in the heating process. There wasn't.
  • the photosensitive coloring composition (RR-1) was coated on a 100 mm ⁇ 100 mm glass substrate with a die coater to a thickness of about 2 ⁇ m, and the solvent was removed and dried in an oven at 70 ° C. for 20 minutes. Subsequently, stripe pattern exposure was performed with ultraviolet rays using an exposure apparatus. The exposure amount was 100 mJ / cm 2 . Furthermore, after spray development with a developer composed of an aqueous sodium carbonate solution to remove unexposed portions, the substrate is washed with ion-exchanged water, and this substrate is heated at 230 ° C. for 30 minutes to form a red filter segment having a line width of about 50 ⁇ m. did. Next, in the same manner, a green filter segment is formed using the green photosensitive coloring composition next to the red filter segment, and then a blue filter segment is formed using the blue photosensitive coloring composition. A color filter comprising a color filter segment was obtained.
  • a pigment composition for a color filter a coloring composition, and a pigment composition for a color filter, which have good brightness and contrast and are less likely to cause crystal precipitation of a diketopyrrolopyrrole pigment even in a heating process, are used.
  • a color filter can be provided.

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Abstract

L'invention concerne une composition de pigments du type dicétopyrrolopyrrole pour filtres couleur, qui comprend un pigment de dicétopyrrolopyrrole représenté par la formule (1), et un pigment de dicéetopyrrolopyrrole représenté par la formule (A-2), et qui est caractérisée en ce que la proportion du pigment de dicétopyrrolopyrrole, représenté par la formule (A-2), est de 1-15% en poids par rapport au poids total des pigments du type dicétopyrrolopyrrole.
PCT/JP2012/051888 2011-01-28 2012-01-27 Composition de pigments du type dicétopyrrolopyrrole pour filtres couleur, composition colorée pour filtres couleur et filtre couleur WO2012102399A1 (fr)

Priority Applications (4)

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KR1020137020929A KR101920285B1 (ko) 2011-01-28 2012-01-27 컬러필터용 디케토피롤로피롤계 안료 조성물, 컬러필터용 착색 조성물 및 컬러필터
KR1020187020266A KR101942407B1 (ko) 2011-01-28 2012-01-27 컬러필터용 디케토피롤로피롤계 안료 조성물, 컬러필터용 착색 조성물 및 컬러필터
CN201280006727.XA CN103339536B (zh) 2011-01-28 2012-01-27 彩色滤光片用吡咯并吡咯二酮系颜料组合物、彩色滤光片用着色组合物及彩色滤光片
KR1020187035854A KR101971251B1 (ko) 2011-01-28 2012-01-27 컬러필터용 디케토피롤로피롤계 안료 조성물, 컬러필터용 착색 조성물 및 컬러필터

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JP2011015874A JP5659823B2 (ja) 2011-01-28 2011-01-28 カラーフィルタ用顔料組成物、着色組成物、およびカラーフィルタ
JP2011-015874 2011-01-28
JP2011076928A JP5724537B2 (ja) 2011-03-31 2011-03-31 カラーフィルタ用着色組成物、およびカラーフィルタ
JP2011-076929 2011-03-31
JP2011076929A JP5760596B2 (ja) 2011-03-31 2011-03-31 カラーフィルタ用着色組成物、およびカラーフィルタ
JP2011-076928 2011-03-31

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JPWO2015008734A1 (ja) * 2013-07-15 2017-03-02 花王株式会社 カラーフィルター用着色組成物
WO2015008734A1 (fr) * 2013-07-15 2015-01-22 花王株式会社 Composition colorante pour filtre couleur
JP2015110726A (ja) * 2013-07-22 2015-06-18 Jsr株式会社 着色組成物、着色硬化膜、並びに表示素子及び固体撮像素子
KR20170036748A (ko) 2014-09-04 2017-04-03 후지필름 가부시키가이샤 조성물, 조성물의 제조 방법, 경화성 조성물, 경화막, 근적외선 차단 필터, 고체 촬상 소자, 적외선 센서 및 카메라 모듈
WO2019054281A1 (fr) 2017-09-15 2019-03-21 富士フイルム株式会社 Composition, film, stratifié, filtre de transmission infrarouge, dispositif d'imagerie à semi-conducteurs et capteur infrarouge
JP7087788B2 (ja) 2018-07-30 2022-06-21 東洋インキＳｃホールディングス株式会社 固体撮像素子用カラーフィルタの感光性着色組成物、カラーフィルタ、およびそれを用いた固体撮像素子
JP2020020851A (ja) * 2018-07-30 2020-02-06 東洋インキＳｃホールディングス株式会社 固体撮像素子用カラーフィルタの感光性着色組成物、カラーフィルタ、およびそれを用いた固体撮像素子
WO2020059509A1 (fr) 2018-09-20 2020-03-26 富士フイルム株式会社 Composition durcissable, film durci, filtre de transmission infrarouge, stratifié, élément d'imagerie à l'état solide, capteur, et procédé de formation de motif
WO2020241535A1 (fr) 2019-05-31 2020-12-03 富士フイルム株式会社 Capteur optique et dispositif de détection
WO2021039205A1 (fr) 2019-08-29 2021-03-04 富士フイルム株式会社 Composition, film, filtre éliminateur d'infrarouge proche, procédé de formation de motif, stratifié, élément d'imagerie à semi-conducteurs, capteur infrarouge, dispositif d'affichage d'image, module de caméra et composé
WO2021039253A1 (fr) 2019-08-30 2021-03-04 富士フイルム株式会社 Composition, film, filtre optique et procédé de production associé, élément d'imagerie à semi-conducteurs, capteur infrarouge et module de capteur
WO2022014635A1 (fr) 2020-07-15 2022-01-20 東洋インキＳｃホールディングス株式会社 Composition de pigments, composition colorante, peinture, encre, ensemble d'encres, article imprimé et matériau d'emballage
WO2022131191A1 (fr) 2020-12-16 2022-06-23 富士フイルム株式会社 Composition, membrane, filtre optique, élément de capture d'image solide, appareil d'affichage d'image et capteur de rayons infrarouges
WO2022130773A1 (fr) 2020-12-17 2022-06-23 富士フイルム株式会社 Composition, film, filtre optique, élément d'imagerie à semi-conducteurs, dispositif d'affichage d'image et capteur infrarouge
WO2023013332A1 (fr) 2021-08-03 2023-02-09 東洋インキＳｃホールディングス株式会社 Composition de pigment, composition de colorant, peinture, encre, ensemble d'encres, article imprimé et matériau d'emballage

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KR101971251B1 (ko) 2019-04-22
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TWI510561B (zh) 2015-12-01
KR20180083965A (ko) 2018-07-23
KR20180135982A (ko) 2018-12-21
KR101920285B1 (ko) 2018-11-21
KR20140037818A (ko) 2014-03-27
CN103339536B (zh) 2015-07-22
CN103339536A (zh) 2013-10-02

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