WO2014021328A1 - 着色組成物、カラーフィルタ及び表示素子 - Google Patents

着色組成物、カラーフィルタ及び表示素子 Download PDF

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WO2014021328A1
WO2014021328A1 PCT/JP2013/070626 JP2013070626W WO2014021328A1 WO 2014021328 A1 WO2014021328 A1 WO 2014021328A1 JP 2013070626 W JP2013070626 W JP 2013070626W WO 2014021328 A1 WO2014021328 A1 WO 2014021328A1
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meth
acrylate
acid
pigment
group
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PCT/JP2013/070626
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English (en)
French (fr)
Japanese (ja)
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裕之 小松
翔 松本
佐藤　佳弘
龍　恭一郎
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Jsr株式会社
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Priority to KR20147031878A priority Critical patent/KR20150037741A/ko
Priority to JP2014528174A priority patent/JP6160618B2/ja
Publication of WO2014021328A1 publication Critical patent/WO2014021328A1/ja

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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F20/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
    • C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • 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
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/105—Esters of polyhydric alcohols or polyhydric phenols of pentaalcohols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/106—Esters of polycondensation macromers
    • 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

Definitions

  • the present invention relates to a colored composition, a color filter, and a display element. More specifically, the present invention is useful for a color filter used for a transmissive or reflective color liquid crystal display element, a solid-state imaging element, an organic EL display element, electronic paper, and the like.
  • the present invention relates to a colored composition used for forming a colored layer, a color filter including a colored layer formed using the colored composition, and a display element including the color filter.
  • a pigment-dispersed colored radiation-sensitive composition is applied on a substrate and dried, and then the dried coating film is irradiated with radiation in a desired pattern shape.
  • a method of obtaining pixels of each color by irradiation (hereinafter referred to as “exposure”) and development is known (see, for example, Patent Documents 1 and 2).
  • a method of forming a black matrix using a photopolymerizable composition in which carbon black is dispersed is also known.
  • a method for obtaining pixels of each color by an inkjet method using a pigment-dispersed colored resin composition is also known (see, for example, Patent Document 4).
  • Patent Document 5 proposes the use of a xanthene-based acid dye
  • Patent Document 6 proposes the use of a lake pigment.
  • the subject of this invention is providing the coloring composition containing dye or a lake pigment suitable for formation of the colored layer which can make heat resistance and light resistance compatible.
  • the subject of this invention is providing the display element which comprises the color filter provided with the colored layer formed using the said coloring composition, and the said color filter.
  • the present inventors have conducted intensive research and have used a colorant containing at least one selected from the group consisting of a dye and a lake pigment together with a polyfunctional (meth) acrylate having a specific structure.
  • a colorant containing at least one selected from the group consisting of a dye and a lake pigment together with a polyfunctional (meth) acrylate having a specific structure.
  • the present invention is a colored composition containing (A) a colorant, (B) a binder resin, and (C) a polymerizable compound, and (A) the colorant is selected from the group consisting of a dye and a lake pigment.
  • the present invention provides a coloring composition comprising at least one kind and (C) a polyfunctional (meth) acrylate having a ring structure as a polymerizable compound.
  • the present invention provides a color filter comprising a colored layer formed using the colored composition, and a display element comprising the color filter.
  • the “colored layer” means each color pixel, black matrix, black spacer, etc. used in the color filter.
  • the colored layer formed using the colored composition of the present invention has an excellent balance between heat resistance and light resistance. Surprisingly, it has been found that the colored layer formed using the colored composition of the present invention is also excellent in voltage holding ratio. Therefore, the colored composition of the present invention is used for various color filters including color filters for color liquid crystal display elements, color filters for color separation of solid-state imaging elements, color filters for organic EL display elements, and color filters for electronic paper. It can be used very suitably for production.
  • Coloring composition will be described components of the colored composition of the present invention.
  • the coloring composition of this invention contains at least 1 sort (s) chosen from the group which consists of dye and a lake pigment as a coloring agent.
  • the dye any of acidic dyes, basic dyes and nonionic dyes can be suitably used. These can be used alone or in combination of two or more, and can be arbitrarily combined when two or more are used in combination.
  • the “acidic dye” means an ionic dye in which the anion part becomes a chromophore, and the ionic dye forming a salt with the anion part is also an acid dye.
  • the “basic dye” means an ionic dye having a cation moiety as a chromophore, and an ionic dye forming a salt with the cation moiety is also a basic dye.
  • “Nonionic dye” means a dye other than an acid dye and a basic dye.
  • acid dyes examples include azo acid dyes, triarylmethane acid dyes, anthraquinone acid dyes, xanthene acid dyes, quinoline acid dyes, nitro acid dyes, and cyanine acid dyes. These can be used alone or in combination of two or more, and can be arbitrarily combined when two or more are used in combination.
  • azo acid dye examples include C.I. I. Acid Yellow 11, C.I. I. Acid Orange 7, C.I. I. Acid Red 37, C.I. I. Acid Red 180, C.I. I. Acid Blue 29, C.I. I. Direct Red 28, C.I. I. Direct Red 83, C.I. I. Direct Yellow 12, C.I. I. Direct Orange 26, C.I. I. Direct Green 59, C.I. I. Reactive Yellow 2, C.I. I. Reactive Red 17, C.I. I. Reactive Red 120, C.I. I. Reactive Black 5, C.I. I. Molded Red 7, C.I. I. Moldant Yellow 5, C.I. I. Moldant Black 7, C.I. I. Direct green 28 etc. can be mentioned.
  • triarylmethane acid dyes include C.I. I. Acid Blue 9 etc. can be mentioned.
  • anthraquinone acid dyes include C.I. I. Acid Blue 40, C.I. I. Acid Green 25, C.I. I. Reactive Blue 19, C.I. I. And reactive blue 49.
  • Specific examples of xanthene acid dyes include C.I. I. Acid Red 52, C.I. I. Acid Red 87, C.I. I. Acid Red 92, C.I. I. Acid Red 289, C.I. I. In addition to Acid Red 388, Synthesis Examples 1 to 3 in JP 2010-32999 A and dyes disclosed in JP 2011-138094 A can be given.
  • quinoline acid dyes include C.I. I. Acid Yellow 3 etc. can be mentioned.
  • nitro acid dye include C.I. I. Acid Yellow 1, C.I. I. Acid Orange 3 etc.
  • cyanine acid dyes include C.I. I. Reactive yellow 1 etc. can be mentioned.
  • Examples of basic dyes include azo basic dyes, triarylmethane basic dyes, xanthene basic dyes, quinoneimine basic dyes, and cyanine basic dyes. These can be used alone or in combination of two or more, and can be arbitrarily combined when two or more are used in combination.
  • azo basic dye examples include C.I. I. Basic Blue 41, C.I. I. In addition to Basic Red 18, the dyes described in JP-A-2011-145540 can be exemplified.
  • triarylmethane basic dye examples include C.I. I. In addition to Basic Blue 7, the dyes described in International Publication No. 10/123071, Pamphlet, JP-A 2011-116803, JP-A 2011-117995, and JP-A 2011-133844 can be exemplified.
  • Specific examples of the xanthene-based basic dye include C.I. I. Basic violet 11 and the like can be mentioned.
  • quinoneimine basic dye include C.I. I. Basic Blue 3, C.I. I.
  • Basic Blue 9 etc. can be mentioned.
  • Specific examples of the cyanine basic dye include C.I. I. Basic Red 12, C.I. I. Basic Red 13, C.I. I. Basic Red 14, C.I. I. Basic Violet 7, C.I. I. Basic Violet 16, C.I. I. Basic Yellow 1, C.I. I. Basic Yellow 11, C.I. I. Basic Yellow 13, C.I. I. Basic Yellow 21, C.I. I. Basic Yellow 28, C.I. I. Basic yellow 51 etc. can be mentioned.
  • various basic dyes described in JP-T-2007-503477 can be exemplified.
  • nonionic dyes examples include azo nonionic dyes, anthraquinone nonionic dyes, phthalocyanine nonionic dyes, quinoline nonionic dyes, nitro nonionic dyes, and methine nonionic dyes. Etc. These can be used alone or in combination of two or more, and can be arbitrarily combined when two or more are used in combination.
  • azo nonionic dye examples include C.I. I. Disperse Orange 5, C.I. I. Disperse thread 58, C.I. I. In addition to Disperse Blue 165, dyes described in JP 2010-170073 A, JP 2010-170074 A, JP 2010-275531 A, and JP 2010-275533 A may be mentioned.
  • Specific examples of the anthraquinone nonionic dye include C.I. I. Bat Blue 4, C.I. I. Disperse thread 60, C.I. I. Disperse Blue 56, C.I. I. Disperse Blue 60 etc. can be mentioned.
  • Specific examples of the phthalocyanine-based nonionic dye include C.I. I. Pad blue 5 etc. can be mentioned.
  • quinoline-based nonionic dyes include C.I. I. Solvent Yellow 33, C.I. I. Disperse Yellow 64 and the like.
  • Specific examples of the nitro nonionic dye include C.I. I. Disperse Yellow 42 etc. can be mentioned.
  • Specific examples of the methine nonionic dye include C.I. I. Solvent Yellow 179, Disperse Yellow 201, etc. can be mentioned.
  • various nonionic dyes described in claim 3 or claim 4 of JP2010-168531A can be mentioned.
  • these dyes can be appropriately selected and used, among which acidic dyes and basic dyes are preferable.
  • acidic dyes and basic dyes are preferable.
  • triarylmethane dyes, xanthene dyes, azo dyes, methine dyes, and cyanine dyes are preferable.
  • xanthene acid dyes, triarylmethane acid dyes, triarylmethane basic dyes, and cyanine basic dyes are particularly preferable.
  • lake pigment refers to a soluble dye made into an insoluble pigment by a precipitating agent.
  • the precipitating agent for rake formation include barium chloride, calcium chloride, ammonium sulfate, aluminum chloride, aluminum acetate, lead acetate, tannic acid, katanol, tamol, isopolyacid, heteropolyacid, and the like.
  • the isopolyacid include isopolytungstic acid, isopolyvanadic acid, and isopolymolybdic acid.
  • the heteropolyacid include phosphotungstic acid, phosphomolybdic acid, phosphotungsten molybdic acid, and the like.
  • lake pigments that have been laked using isopolyacid or heteropolyacid as a precipitating agent are preferred, and lake pigments that have been laked using heteropolyacid as a precipitating agent are particularly preferred.
  • a lake pigment raked with an isopolyacid or heteropolyacid as a precipitating agent can be produced, for example, by the method described in JP2011-186043A.
  • the lake pigment is not particularly limited, and examples thereof include xanthene lake pigments, triarylmethane lake pigments, azo lake pigments, and phthalocyanine lake pigments. These can be used alone or in combination of two or more, and can be arbitrarily combined when two or more are used in combination.
  • lake pigments include those with the following color index (CI) names.
  • Pigment red 58 1, C.I. I. Pigment red 58: 2, C.I. I. Pigment red 58: 3, C.I. I. Pigment red 58: 4, C.I. I. Pigment red 60: 1, C.I. I. Pigment red 63, C.I. I. Pigment red 63: 1, C.I. I. Pigment red 63: 2, C.I. I. Pigment red 63: 3, C.I. I. Pigment yellow 61, C.I. I. Pigment yellow 61: 1, C.I. I. Pigment yellow 62, C.I. I. Pigment red 64: 1, C.I. I. Pigment red 68, C.I. I. Pigment red 247, C.I. I.
  • Pigment red 200 C.I. I. Pigment yellow 100, C.I. I. Pigment yellow 104, C.I. I. Pigment yellow 133, C.I. I. Pigment yellow 168, C.I. I. Pigment yellow 169, C.I. I. Pigment yellow 183, C.I. I. Pigment yellow 191, C.I. I. Azo lake pigments such as CI Pigment Yellow 191: 1; C. I. Phthalocyanine lake pigments such as CI Pigment Blue 17: 1.
  • these lake pigments can be appropriately selected and used, among which triarylmethane lake pigments and xanthene lake pigments are preferable, and triarylmethane lake pigments are particularly preferable.
  • the coloring composition of this invention can contain another coloring agent with at least 1 sort (s) chosen from the group which consists of dye and a lake pigment as a coloring agent.
  • Other colorants are not particularly limited, and colors and materials can be appropriately selected according to the application.
  • the other colorant any of pigments other than lake pigments and natural pigments can be used, but organic pigments other than lake pigments are preferred in terms of obtaining pixels having high luminance and color purity.
  • other colorants can be used singly or in combination of two or more, and when two or more are used in combination, they can be arbitrarily combined.
  • organic pigments other than the above-mentioned lake pigments include the color index (CI) name, C.I. I. Pigment red 166, C.I. I. Pigment red 177, C.I. I. Pigment red 224, C.I. I. Pigment red 242, C.I. I. Pigment red 254, C.I. I. Pigment green 7, C.I. I. Pigment green 36, C.I. I. Pigment green 58, C.I. I. Pigment blue 15: 6, C.I. I. Pigment blue 80, C.I. I. Pigment yellow 83, C.I. I. Pigment yellow 138, C.I. I. Pigment yellow 139, C.I. I. Pigment yellow 150, C.I. I. Pigment yellow 180, C.I. I. Pigment yellow 211, C.I. I. Pigment orange 38, C.I. I. And CI Pigment Violet 23.
  • CI color index
  • the pigment when a pigment is used as another colorant, the pigment may be used after being purified by a recrystallization method, a reprecipitation method, a solvent washing method, a sublimation method, a vacuum heating method, or a combination thereof.
  • the pigment surface may be used by modifying the particle surface with a resin if desired.
  • the resin that modifies the pigment particle surface include a vehicle resin described in JP-A No. 2001-108817, or various commercially available resins for dispersing pigments.
  • a resin coating method on the carbon black surface for example, methods described in JP-A-9-71733, JP-A-9-95625, JP-A-9-124969, and the like can be employed.
  • the organic pigment may be used after the primary particles are refined by so-called salt milling.
  • a salt milling method for example, a method disclosed in Japanese Patent Laid-Open No. 8-179111 can be employed.
  • a known dispersant and dispersion aid can be further added.
  • Known dispersants include, for example, urethane dispersants, polyethylene imine dispersants, polyoxyethylene alkyl ether dispersants, polyoxyethylene alkyl phenyl ether dispersants, polyethylene glycol diester dispersants, sorbitan fatty acid ester dispersants.
  • Dispersants, polyester dispersants, acrylic dispersants and the like can be mentioned, and examples of the dispersion aid include pigment derivatives.
  • Such dispersants are commercially available.
  • acrylic dispersants such as Disperbyk-2000, Disperbyk-2001, BYK-LPN6919, BYK-LPN21116, BYK-LPN21324 (above, BYK Corporation (BYK) Etc.) as a urethane-based dispersant, Disperbyk-161, Disperbyk-162, Disperbyk-165, Disperbyk-167, Disperbyk-170, Disperbyk-182, DISPERBYK-2164 (above, manufactured by BYK SPARS) 76500 (manufactured by Lubrizol) as a polyethyleneimine-based dispersant, Solsperse 24000 (manufactured by Lubrizol), etc., polyester-based dispersion As, Ajisper PB821, Ajisper PB822, Ajisper PB880, Ajisper PB881 (above, manufactured by Ajinomoto Fine-Techno Co.,
  • pigment derivative examples include copper phthalocyanine, diketopyrrolopyrrole, and sulfonic acid derivatives of quinophthalone.
  • the coloring composition of the present invention is preferably used for forming a blue pixel or a red pixel when a triarylmethane dye or lake pigment, or a xanthene dye or lake pigment is used as the colorant (A).
  • the colorant is used in combination with at least one selected from the group consisting of purple organic pigments and blue organic pigments, together with the dyes and lake pigments described above. Is preferable from the viewpoint of chromaticity characteristics. I. Pigment blue 15: 6 and C.I. I. It is preferable to use in combination with at least one selected from the group consisting of CI Pigment Violet 23.
  • the colorant is used in combination with at least one selected from the group consisting of a red organic pigment and a purple organic pigment together with the above-mentioned dye and lake pigment.
  • a red organic pigment and a purple organic pigment together with the above-mentioned dye and lake pigment.
  • the content of the colorant (A) is usually 5 to 70% by mass, preferably 5 to 70% by mass in the solid content of the coloring composition from the viewpoint of forming a pixel having high luminance and excellent color purity, or a black matrix having excellent light shielding properties. 10 to 60% by mass. Solid content here is components other than the solvent mentioned later. Further, the total content of at least one selected from the group consisting of dyes and lake pigments is appropriately determined according to the required chromaticity, but is preferably 30% by mass or more in all colorants. Preferably it is 60 mass% or more. By setting it as such an aspect, the colored layer excellent in heat resistance can be formed.
  • Binder resin Although it does not specifically limit as (B) binder resin in this invention, it is resin which has acidic functional groups, such as a carboxyl group and a phenolic hydroxyl group. Among them, a polymer having a carboxyl group (hereinafter also referred to as “carboxyl group-containing polymer”) is preferable. For example, an ethylenically unsaturated monomer having one or more carboxyl groups (hereinafter referred to as “unsaturated monomer”). And a copolymer of another copolymerizable ethylenically unsaturated monomer (hereinafter also referred to as “unsaturated monomer (b2)”). .
  • unsaturated monomer (b1) examples include (meth) acrylic acid, maleic acid, maleic anhydride, succinic acid mono [2- (meth) acryloyloxyethyl], ⁇ -carboxypolycaprolactone mono (meta ) Acrylate, p-vinylbenzoic acid and the like. These unsaturated monomers (b1) can be used alone or in admixture of two or more.
  • unsaturated monomer (b2) for example, N-substituted maleimides such as N-phenylmaleimide and N-cyclohexylmaleimide; Aromatic vinyl compounds such as styrene, ⁇ -methylstyrene, p-hydroxystyrene, p-hydroxy- ⁇ -methylstyrene, p-vinylbenzylglycidyl ether, acenaphthylene;
  • N-substituted maleimides such as N-phenylmaleimide and N-cyclohexylmaleimide
  • Aromatic vinyl compounds such as styrene, ⁇ -methylstyrene, p-hydroxystyrene, p-hydroxy- ⁇ -methylstyrene, p-vinylbenzylglycidyl ether, acenaphthylene;
  • Vinyl ethers such as cyclohexyl vinyl ether, isobornyl vinyl ether, tricyclo [5.2.1.0 2,6 ] decan-8-yl vinyl ether, pentacyclopentadecanyl vinyl ether, 3- (vinyloxymethyl) -3-ethyloxetane ;
  • Examples thereof include a macromonomer having a mono (meth) acryloyl group at the end of a polymer molecular chain such as polystyrene, polymethyl (meth) acrylate, poly-n-butyl (meth) acrylate and polysiloxane.
  • These unsaturated monomers (b2) can be used alone or in admixture of two or more.
  • the copolymerization ratio of the unsaturated monomer (b1) in the copolymer is preferably 5 to 50% by mass. More preferably, it is 10 to 40% by mass.
  • copolymer of the unsaturated monomer (b1) and the unsaturated monomer (b2) include, for example, JP-A-7-140654, JP-A-8-259876, and JP-A-10-31308. No. 10, JP-A-10-300902, JP-A-11-174224, JP-A-11-258415, JP-A-2000-56118, JP-A-2004-101728, etc. Coalescence can be mentioned.
  • a carboxyl group-containing polymer having a polymerizable unsaturated bond such as a (meth) acryloyl group in the side chain can also be used as a binder resin.
  • the binder resin in the present invention has a polystyrene-reduced weight average molecular weight (Mw) measured by gel permeation chromatography (hereinafter abbreviated as GPC) (elution solvent: tetrahydrofuran), usually 1,000 to 100,000, preferably Is 3,000 to 50,000. If Mw is too small, the remaining film rate of the resulting film may be reduced, pattern shape, heat resistance, etc. may be impaired, and electrical characteristics may be deteriorated. On the other hand, if Mw is too large, resolution may be reduced. In addition, the pattern shape may be damaged, and dry foreign matter may be easily generated during application by the slit nozzle method.
  • Mw polystyrene-reduced weight average molecular weight measured by gel permeation chromatography
  • the ratio (Mw / Mn) of the weight average molecular weight (Mw) to the number average molecular weight (Mn) of the binder resin in the present invention is preferably 1.0 to 5.0, more preferably 1.0 to 3. .0.
  • Mn here says the number average molecular weight of polystyrene conversion measured by GPC (elution solvent: tetrahydrofuran).
  • the binder resin in the present invention can be produced by a known method. For example, it is disclosed in Japanese Patent Application Laid-Open No. 2003-222717, Japanese Patent Application Laid-Open No. 2006-259680, International Publication No. 07/029871, etc.
  • the structure, Mw, and Mw / Mn can be controlled by the method.
  • the binder resins can be used alone or in admixture of two or more.
  • the content of the binder resin is usually 10 to 1,000 parts by weight, preferably 20 to 500 parts by weight with respect to 100 parts by weight of the colorant (A). If the content of the binder resin is too small, for example, the alkali developability may be decreased, or the storage stability of the resulting colored composition may be decreased. On the other hand, if the content is too large, the colorant concentration is relatively high. Therefore, it may be difficult to achieve the target color density as a thin film.
  • the coloring composition of the present invention contains a polyfunctional (meth) acrylate having a ring structure as a polymerizable compound.
  • the polyfunctional (meth) acrylate having a ring structure is not particularly limited as long as it has one or more ring structures and two or more (meth) acryloyl groups in the molecule.
  • Examples of the ring structure include alicyclic hydrocarbon rings, aromatic hydrocarbon rings, and heterocyclic rings.
  • the alicyclic hydrocarbon ring is preferably an alicyclic hydrocarbon ring having 4 to 30 carbon atoms, more preferably 4 to 18 carbon atoms, and still more preferably 4 to 10 carbon atoms.
  • the alicyclic hydrocarbon ring includes cycloalkane, cycloalkene, condensed polycyclic hydrocarbon, bridged ring hydrocarbon, spiro hydrocarbon, cyclic terpene hydrocarbon and the like.
  • These alicyclic hydrocarbon rings may further have an alkyl group, a halogen atom, a carboxyl group, a carbonyl group or the like as a substituent.
  • alkyl group include methyl group, ethyl group, propyl group, isopropyl group, butyl group, s-butyl group, t-butyl group, pentyl group, isopentyl group, and hexyl group. Of these, an alkyl group having 1 to 4 carbon atoms is preferable.
  • the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • the aromatic hydrocarbon ring is preferably an aromatic hydrocarbon ring having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and further 6 to 10 carbon atoms.
  • a benzene ring, naphthalene ring, anthracene ring, phenanthrene is preferred.
  • Aromatic hydrocarbon rings such as a ring, a pyrene ring, a biphenyl ring and a perylene ring can be exemplified. These aromatic hydrocarbon rings can further have a substituent, and examples of the substituent include the same as in the case of the alicyclic hydrocarbon ring. Also, two or more of these aromatic hydrocarbon ring, an alkanediyl group, -O -, - CO -, - COO -, - OCO -, - OSO 2 -, - SO 2 -, - OSO 2 NR'-, It can also be linked via at least one divalent group selected from the group consisting of —NR′CO— and —CONR′—.
  • R ′ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • aromatic hydrocarbon rings benzene rings, aromatic hydrocarbon rings in which two benzene rings such as diphenyl ether are connected by —O—, and aromatics in which two benzene rings such as benzophenone are connected by —CO—.
  • a group hydrocarbon ring is preferred.
  • the heterocyclic ring is preferably a heterocyclic ring having 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, and further 3 to 10 carbon atoms.
  • Alicyclic heterocycles such as chromane, pyridine, pyrazine, pyrimidine, pyridazine, pyrrole, imidazole, pyrazole, quinoline, isoquinoline, phthalazine, naphthyridine, quinoxaline, furan, pyran, thiazoline, oxazole, indole, indazole, thiophene, purine,
  • Aromatic heterocycles such as carbazole, xanthene, acridine, phenazine, thianthrene, phenothiazine, phenoxazine, and phenanthroline can be given.
  • heterocyclic rings can further have a substituent, and examples of the substituent include the same as those in the case of the alicyclic hydrocarbon ring.
  • aromatic heterocycles are preferable, and pyridine, pyrazine, pyrimidine, pyrazole, quinoline, and carbazole are particularly preferable.
  • the polyfunctional (meth) acrylate having a ring structure of the present invention may have a ring structure at an arbitrary position in the molecule.
  • the polyfunctional (meth) acrylate having a ring structure of the present invention preferably further has a carboxyl group from the viewpoint that the effects of the present invention are remarkably enhanced.
  • the said carboxyl group can have in the arbitrary positions in the molecule
  • a polyfunctional (meth) acrylate having such a ring structure can be obtained, for example, by subjecting a polyfunctional (meth) acrylate having a hydroxyl group to a condensation reaction with an acid anhydride having a ring structure.
  • a crude condensate obtained by removing a solvent, an acid anhydride, or the like from the product may be used, or a purified condensate isolated from the reaction product may be used.
  • a well-known method is employable for a condensation reaction.
  • Examples of the polyfunctional (meth) acrylate having a hydroxyl group include trimethylolpropane di (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, and glycerol dimethacrylate. .
  • pentaerythritol tri (meth) acrylate and dipentaerythritol penta (meth) acrylate are preferable.
  • the acid anhydride having a ring structure is preferably a polybasic acid anhydride having a ring structure, specifically, tetrahydrophthalic acid anhydride, methyltetrahydrophthalic acid anhydride, hexahydrophthalic acid anhydride.
  • Dibasic acid anhydrides having an aromatic hydrocarbon ring Tribasic acid monoanhydrides having aromatic hydrocarbon rings such as trimellitic anhydride, py
  • dibasic acid anhydrides having an alicyclic hydrocarbon ring or aromatic hydrocarbon ring dibasic acid anhydrides having an alicyclic hydrocarbon ring or aromatic hydrocarbon ring
  • polybasic acid dianhydrides having a tetrabasic acid or higher having an alicyclic hydrocarbon ring or aromatic hydrocarbon ring are included.
  • a dibasic acid anhydride having an alicyclic hydrocarbon ring or an aromatic hydrocarbon ring is more preferable.
  • the polyfunctional (meth) acrylate having a ring structure preferably contains a compound represented by the following formula (1) or a compound represented by the following formula (2).
  • R 1 represents a hydrogen atom or a methyl group
  • X represents a substituted or unsubstituted divalent alicyclic hydrocarbon group or a substituted or unsubstituted divalent aromatic hydrocarbon group
  • m represents an integer of 0 to 4.
  • R 1 represents a hydrogen atom or a methyl group
  • Y represents a substituted or unsubstituted tetravalent alicyclic hydrocarbon group or a substituted or unsubstituted tetravalent aromatic hydrocarbon group
  • n1 and n2 each independently represent an integer of 0 to 4.
  • X represents a substituted or unsubstituted divalent alicyclic hydrocarbon group or a substituted or unsubstituted divalent aromatic hydrocarbon group.
  • alicyclic hydrocarbon group and aromatic hydrocarbon group And residues obtained by removing two hydrogen atoms from the aforementioned alicyclic hydrocarbon ring and aromatic hydrocarbon ring.
  • m represents an integer of 0 to 4, preferably an integer of 0 to 2, and more preferably 0 or 1.
  • Y represents a substituted or unsubstituted tetravalent alicyclic hydrocarbon group or a substituted or unsubstituted tetravalent aromatic hydrocarbon group.
  • the alicyclic hydrocarbon group and aromatic hydrocarbon group include And residues obtained by removing four hydrogen atoms from the aforementioned alicyclic hydrocarbon ring and aromatic hydrocarbon ring.
  • n1 and n2 each independently represent an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 0 or 1.
  • Polyfunctional (meth) acrylates having such a ring structure include, for example, pentaerythritol triacrylate modified with phthalic anhydride, pentaerythritol triacrylate modified with tetrahydrophthalic anhydride, pentaerythritol triacrylate with hexahydrophthalic anhydride Modified products, hydrated anhydride modified products of pentaerythritol triacrylate, trifunctional (meth) acrylates containing carboxyl groups, such as methyl-hexahydrophthalic anhydride modified products of pentaerythritol triacrylate, phthalic anhydride modified products of dipentaerythritol pentaacrylate , Tetrahydrophthalic anhydride modified dipentaerythritol pentaacrylate, hexahydrophthalic anhydride modified dipentaerythritol pentaacrylate, di Examples thereof include a carboxyl group-containing pen
  • the acid value of the polyfunctional (meth) acrylate having a ring structure is preferably 10 to 250 mgKOH / g, more preferably 20 to 200 mgKOH / g, further 40 to 170 mgKOH / g, and further 55 to 130 mgKOH / g. Further, it is preferably 60 to 100 mgKOH / g.
  • the other polymerizable compound in the present invention refers to a compound having two or more polymerizable groups.
  • the polymerizable group include an ethylenically unsaturated group, a ⁇ -butyrolactone group, an oxiranyl group, an oxetanyl group, and an N-alkoxymethylamino group.
  • the other polymerizable compound includes a compound having two or more (meth) acryloyloxy groups (excluding the polyfunctional (meth) acrylate having the ring structure), or two or more N-alkoxy.
  • a compound having a methylamino group is preferred.
  • Specific examples of the compound having two or more (meth) acryloyloxy groups include a reaction between an aliphatic polyhydroxy compound and (meth) acrylic acid. Obtained by reacting a polyfunctional (meth) acrylate, a caprolactone-modified polyfunctional (meth) acrylate, an alkylene oxide-modified polyfunctional (meth) acrylate, a hydroxyl-containing (meth) acrylate and a polyfunctional isocyanate. Examples thereof include polyfunctional urethane (meth) acrylates, polyfunctional (meth) acrylates having a carboxyl group obtained by reacting (meth) acrylates having a hydroxyl group with acid anhydrides having no ring structure.
  • examples of the aliphatic polyhydroxy compound include divalent aliphatic polyhydroxy compounds such as ethylene glycol, propylene glycol, polyethylene glycol, and polypropylene glycol, glycerin, trimethylolpropane, pentaerythritol, and dipentaerythritol. Mention may be made of trivalent or higher aliphatic polyhydroxy compounds.
  • Specific examples of the (meth) acrylate having a hydroxyl group include those similar to the above-mentioned polyfunctional (meth) acrylate having a hydroxyl group in addition to 2-hydroxyethyl (meth) acrylate.
  • polyfunctional isocyanate examples include tolylene diisocyanate, hexamethylene diisocyanate, diphenylmethylene diisocyanate, and isophorone diisocyanate.
  • acid anhydride having no ring structure examples include aliphatic dibasic acid anhydrides such as succinic anhydride, maleic anhydride, glutaric anhydride, and itaconic anhydride.
  • Examples of the caprolactone-modified polyfunctional (meth) acrylate include the compounds described in paragraphs [0015] to [0018] of JP-A No. 11-44955.
  • Examples of the polyfunctional (meth) acrylate modified with alkylene oxide include di (meth) acrylate modified with at least one selected from ethylene oxide adduct of bisphenol A and propylene oxide adduct of bisphenol A, ethylene of isocyanuric acid At least one selected from tri (meth) acrylate modified with at least one selected from an oxide adduct and a propylene oxide adduct of isocyanuric acid, an ethylene oxide adduct of trimethylolpropane and a propylene oxide adduct of trimethylolpropane Selected from tri (meth) acrylates modified with, ethylene oxide adduct of pentaerythritol and propylene oxide adduct of pentaerythritol Of tetra (me
  • Examples of the compound having two or more N-alkoxymethylamino groups include compounds having a melamine structure, a benzoguanamine structure, and a urea structure.
  • the melamine structure and the benzoguanamine structure refer to a chemical structure having one or more triazine rings or phenyl-substituted triazine rings as a basic skeleton, and is a concept including melamine, benzoguanamine or a condensate thereof.
  • Specific examples of the compound having two or more N-alkoxymethylamino groups include N, N, N ′, N ′, N ′′, N ′′ -hexa (alkoxymethyl) melamine, N, N, N ′. , N′-tetra (alkoxymethyl) benzoguanamine, N, N, N ′, N′-tetra (alkoxymethyl) glycoluril, and the like.
  • polyfunctional (meth) acrylates obtained by reacting trivalent or higher aliphatic polyhydroxy compounds with (meth) acrylic acid, polyfunctional (meth) acrylates modified with caprolactone, Functional urethane (meth) acrylate, polyfunctional (meth) acrylate having carboxyl group, N, N, N ′, N ′, N ′′, N ′′ -hexa (alkoxymethyl) melamine, N, N, N ′, N′-tetra (alkoxymethyl) benzoguanamine is preferred.
  • polyfunctional (meth) acrylates obtained by reacting trivalent or higher aliphatic polyhydroxy compounds with (meth) acrylic acid, trimethylolpropane triacrylate and dipentaerythritol hexaacrylate are polyfunctional having a carboxyl group.
  • (meth) acrylates compounds obtained by reacting pentaerythritol triacrylate and succinic anhydride, and compounds obtained by reacting dipentaerythritol pentaacrylate and succinic anhydride have high strength of the colored layer and are colored. It is particularly preferable in that the layer has excellent surface smoothness and hardly causes scumming or film residue on the unexposed portion of the substrate and the light shielding layer.
  • another polymeric compound can be used individually or in mixture of 2 or more types.
  • the total content of the polymerizable compound (C) in the present invention is usually 5 to 500 parts by weight, preferably 20 to 300 parts by weight with respect to 100 parts by weight of the (B) alkali-soluble resin.
  • the content ratio of the polyfunctional (meth) acrylate having a ring structure in the polymerizable compound (C) is 25 to It is preferably 95% by mass, more preferably 35 to 90% by mass, and further preferably 50 to 80% by mass.
  • the content ratio of the polyfunctional (meth) acrylate having a ring structure in the polymerizable compound (C) is such that the acid value of the polymerizable compound (C) is 1 to 150 mgKOH / g, further 10 to 10 mgKOH / g, Further, it is preferable to appropriately select 20 to 90 mgKOH / g, further 30 to 80 mgKOH / g, and further 40 to 60 mgKOH / g. By setting it as such an aspect, since the desired effect of this invention is acquired more notably, it is preferable.
  • the coloring composition of the present invention can contain a photopolymerization initiator. Thereby, radiation sensitivity can be provided to a coloring composition.
  • the photopolymerization initiator used in the present invention is a polyfunctional (meth) acrylate having a ring structure and other polymerizable compounds optionally added by exposure to radiation such as visible light, ultraviolet light, far ultraviolet light, electron beam, and X-ray. Is a compound that generates active species capable of initiating polymerization.
  • photopolymerization initiators examples include thioxanthone compounds, acetophenone compounds, biimidazole compounds, triazine compounds, O-acyloxime compounds, onium salt compounds, benzoin compounds, benzophenone compounds, ⁇ -Diketone compounds, polynuclear quinone compounds, diazo compounds, imide sulfonate compounds, onium salt compounds, and the like.
  • the photopolymerization initiators can be used alone or in admixture of two or more.
  • the photopolymerization initiator preferably contains at least one selected from the group consisting of thioxanthone compounds, acetophenone compounds, biimidazole compounds, triazine compounds, and O-acyloxime compounds.
  • thioxanthone compounds include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-dichlorothioxanthone, 2 , 4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone and the like.
  • acetophenone compound examples include 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4 -Morpholinophenyl) butan-1-one, 2- (4-methylbenzyl) -2- (dimethylamino) -1- (4-morpholinophenyl) butan-1-one, and the like.
  • biimidazole compound examples include 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetraphenyl-1,2′-biimidazole, 2,2 ′.
  • -Bis (2,4-dichlorophenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis (2,4,6-trichlorophenyl) -4, 4 ′, 5,5′-tetraphenyl-1,2′-biimidazole and the like can be mentioned.
  • a hydrogen donor in terms of improving sensitivity.
  • the “hydrogen donor” as used herein means a compound that can donate a hydrogen atom to a radical generated from a biimidazole compound by exposure.
  • the hydrogen donor include mercaptan-based hydrogen donors such as 2-mercaptobenzothiazole and 2-mercaptobenzoxazole; 4,4′-bis (dimethylamino) benzophenone, 4,4′-bis (diethylamino) benzophenone, etc.
  • an amine-based hydrogen donor can be used alone or in admixture of two or more. However, one or more mercaptan hydrogen donors and one or more amine hydrogen donors are used in combination. It is preferable that the sensitivity can be further improved.
  • triazine compound examples include 2,4,6-tris (trichloromethyl) -s-triazine, 2-methyl-4,6-bis (trichloromethyl) -s-triazine, 2- [2 -(5-Methylfuran-2-yl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- [2- (furan-2-yl) ethenyl] -4,6-bis (trichloro Methyl) -s-triazine, 2- [2- (4-diethylamino-2-methylphenyl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- [2- (3,4-dimethoxy) Phenyl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- (4-methoxyphenyl) -4,6-bis (t
  • O-acyloxime compounds include 1,2-octanedione, 1- [4- (phenylthio) phenyl]-, 2- (O-benzoyloxime), ethanone, 1- [9-ethyl.
  • a sensitizer when using a photopolymerization initiator other than a biimidazole compound such as an acetophenone compound, a sensitizer can be used in combination.
  • a sensitizer include 4,4′-bis (dimethylamino) benzophenone, 4,4′-bis (diethylamino) benzophenone, 4-diethylaminoacetophenone, 4-dimethylaminopropiophenone, and 4-dimethyl.
  • the sensitivity of a coloring composition can be improved by including the polyfunctional thiol which acts as a chain transfer agent.
  • chain transfer agents examples include trimethylolpropane tris (3-mercaptopropionate), pentaerythritol tetrakis (3-mercaptopropionate), 2,4,6-trimercapto-s-triazine, 2 -(N, N-dibutylamino) -4,6-dimercapto-s-triazine and the like can be mentioned.
  • the content of the photopolymerization initiator is preferably 0.01 to 120 parts by weight, more preferably 1 to 100 parts by weight, with respect to 100 parts by weight of the total amount of the polymerizable compound (C). Part by mass is more preferable, and 5 to 30 parts by mass is further preferable. In this case, if the content of the photopolymerization initiator is too small, curing by exposure may be insufficient. On the other hand, if the content is too large, the formed colored layer tends to be detached from the substrate during development.
  • the colored composition of the present invention contains the above components (A) to (C) and other components optionally added, but is usually prepared as a liquid composition by blending a solvent.
  • a solvent As the solvent, as long as the components (A) to (C) and other components constituting the colored composition are dispersed or dissolved and do not react with these components and have appropriate volatility, the solvent is appropriately used. You can choose to use.
  • Ethylene glycol monomethyl ether Ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol mono-n- Butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, di Propylene glycol mono Chirueteru, dipropylene glycol mono -n- propyl ether, dipropylene glycol mono -n- butyl ether, tripropylene glycol monomethyl ether,
  • Lactic acid alkyl esters such as methyl lactate and ethyl lactate; (Cyclo) alkyl alcohols such as methanol, ethanol, propanol, butanol, isopropanol, isobutanol, t-butanol, octanol, 2-ethylhexanol, cyclohexanol; Keto alcohols such as diacetone alcohol;
  • Diacetates such as propylene glycol diacetate, 1,3-butylene glycol diacetate, and 1,6-hexanediol diacetate; Alkoxycarboxylic esters such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl ethoxyacetate, 3-methyl-3-methoxybutylpropionate ; Ethyl acetate, n-propyl acetate, i-propyl acetate, n-butyl acetate, i-butyl acetate, n-amyl formate, i-amyl acetate, n-butyl propionate, ethyl butyrate, n-propyl butyrate, i-butyric acid Other esters such as -propyl, n-butyl butyrate, methyl pyr
  • the solvents can be used alone or in admixture of two or more.
  • propylene glycol mono C 1-4 alkyl ethers such as propylene glycol monomethyl ether and propylene glycol monoethyl ether; ethylene glycol monomethyl ether acetate, propylene glycol from the viewpoints of solubility, pigment dispersibility, coatability, etc.
  • C 2-4 alkylene glycol mono C 1-4 alkyl ether acetate such as monomethyl ether acetate and propylene glycol monoethyl ether acetate; diethylene glycol di C 1-4 alkyl ether such as diethylene glycol dimethyl ether and diethylene glycol methyl ethyl ether; cyclohexanone, 2-heptanone 3-heptanone, 1,3-butylene glycol diacetate, 1,6-hexanediol diacetate, ethyl lactate, Ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, 3-methyl-3-methoxybutylpropionate, n-butyl acetate, i-butyl acetate, n-amyl formate, acetic acid Preferred are i-amyl, n-butyl propionate, ethyl butyrate, i-propy
  • the content of the solvent is not particularly limited, but the total concentration of each component excluding the solvent of the coloring composition is preferably 5 to 50% by mass, and preferably 10 to 40% by mass. More preferred.
  • the coloring composition of this invention can also contain a various additive as needed.
  • additives include fillers such as glass and alumina; polymer compounds such as polyvinyl alcohol and poly (fluoroalkyl acrylates); surfactants such as fluorosurfactants and silicon surfactants; vinyl Trimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxy Silane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-chloropropylmethyl Dimeth
  • the color filter of the present invention includes a colored layer formed using the colored composition of the present invention.
  • a light shielding layer black matrix
  • pre-baking is performed to evaporate the solvent, thereby forming a coating film.
  • post-baking is performed to form a pixel array in which blue pixel patterns are arranged in a predetermined arrangement.
  • each radiation sensitive coloring composition of green or red application of each radiation sensitive coloring composition, pre-baking, exposure, development, and post-baking are performed in the same manner as described above to obtain a green pixel array and red color.
  • a color filter in which pixel arrays of the three primary colors of red, green and blue are arranged on the substrate is obtained.
  • the order of forming pixels of each color is not limited to the above.
  • any one or more of the red, green, and blue pixel arrays may be a colored layer formed using the colored composition of the present invention.
  • a black matrix can be formed by forming a metal thin film such as chromium formed by sputtering or vapor deposition into a desired pattern using a photolithography method, but a black colorant is dispersed together with a lake pigment.
  • a metal thin film such as chromium formed by sputtering or vapor deposition into a desired pattern using a photolithography method
  • a black colorant is dispersed together with a lake pigment.
  • the radiation-sensitive colored composition thus formed, it can be formed in the same manner as in the case of forming the pixel.
  • the coloring composition of the present invention can also be suitably used for forming such a black matrix.
  • the substrate used when forming the color filter examples include glass, silicon, polycarbonate, polyester, aromatic polyamide, polyamideimide, and polyimide.
  • these substrates may be subjected to appropriate pretreatment such as chemical treatment with a silane coupling agent or the like, plasma treatment, ion plating, sputtering, gas phase reaction method, vacuum deposition, etc., if desired.
  • an appropriate coating method such as a spray method, a roll coating method, a spin coating method (spin coating method), a slit die coating method, or a bar coating method may be employed.
  • a spin coating method or a slit die coating method it is preferable to employ a spin coating method or a slit die coating method.
  • Pre-baking is usually performed by a combination of vacuum drying and heat drying.
  • the drying under reduced pressure is usually performed until reaching 50 to 200 Pa.
  • the conditions for heat drying are usually about 70 to 110 ° C. and about 1 to 10 minutes.
  • the coating thickness is usually 0.6 to 8 ⁇ m, preferably 1.2 to 5 ⁇ m, as the film thickness after drying.
  • Examples of radiation light sources used in forming pixels and / or black matrices include xenon lamps, halogen lamps, tungsten lamps, high pressure mercury lamps, ultrahigh pressure mercury lamps, metal halide lamps, medium pressure mercury lamps, and low pressure mercury lamps. Examples thereof include a light source, a laser light source such as an argon ion laser, a YAG laser, a XeCl excimer laser, and a nitrogen laser. An ultraviolet LED can also be used as the exposure light source. Radiation having a wavelength in the range of 190 to 450 nm is preferred.
  • the exposure dose of radiation is preferably 10 to 10,000 J / m 2 .
  • the alkali developer include sodium carbonate, sodium hydroxide, potassium hydroxide, tetramethylammonium hydroxide, choline, 1,8-diazabicyclo- [5.4.0] -7-undecene, 1, An aqueous solution of 5-diazabicyclo- [4.3.0] -5-nonene or the like is preferable.
  • a water-soluble organic solvent such as methanol or ethanol, a surfactant or the like
  • a shower development method a spray development method, a dip (immersion) development method, a paddle (liquid accumulation) development method, or the like
  • the development conditions are preferably 5 to 300 seconds at room temperature.
  • the post-baking conditions are usually 180 to 280 ° C. for about 10 to 60 minutes, but from the viewpoint of the heat resistance of the present colorant, the post-baking temperature is preferably 240 ° C. or less, more preferably 230 ° C. or less. More preferably, it is 200 degrees C or less.
  • the film thickness of the pixel thus formed is usually 0.5 to 5 ⁇ m, preferably 1 to 3 ⁇ m.
  • a method for obtaining pixels of each color by an ink jet method disclosed in Japanese Patent Laid-Open Nos. 7-318723 and 2000-310706 can be employed.
  • a partition having a light shielding function is formed on the surface of the substrate.
  • the liquid composition of the blue thermosetting coloring composition of the present invention is discharged into the formed partition wall by an inkjet apparatus, and then prebaked to evaporate the solvent.
  • the coating film is exposed as necessary, and then cured by post-baking to form a blue pixel pattern.
  • any one or more of the red, green, and blue pixel arrays may be a colored layer formed using the colored composition of the present invention.
  • the partition has not only a light shielding function but also a function for preventing the color composition of each color discharged in the section from being mixed, so that the film is a film compared to the black matrix used in the first method described above. Thick. Therefore, a partition is normally formed using a black radiation sensitive composition.
  • the substrate used when forming the color filter, the light source of radiation, and the pre-baking and post-baking methods and conditions are the same as in the first method described above. In this way, the film thickness of the pixel formed by the ink jet method is approximately the same as the height of the partition wall.
  • a protective film is formed on the pixel pattern thus obtained as necessary, and then a transparent conductive film is formed by sputtering.
  • a spacer can be further formed to form a color filter.
  • the spacer is usually formed using a radiation-sensitive composition, but may be a light-shielding spacer (black spacer).
  • a radiation-sensitive colored composition in which a black colorant is dispersed is used, but the colored composition of the present invention can also be suitably used for forming such a black spacer. Since the color filter of the present invention thus obtained has extremely high luminance and color purity, it is extremely useful for color liquid crystal display elements, color image pickup tube elements, color sensors, organic EL display elements, electronic paper, and the like.
  • the display element of the present invention comprises the color filter of the present invention.
  • the display element include a color liquid crystal display element, an organic EL display element, and electronic paper.
  • the color liquid crystal display element provided with the color filter of the present invention may be a transmissive type or a reflective type, and can have an appropriate structure.
  • the color filter is formed on a substrate different from the driving substrate on which the thin film transistor (TFT) is arranged, and the driving substrate and the substrate on which the color filter is formed are opposed to each other with a liquid crystal layer interposed therebetween.
  • TFT thin film transistor
  • a substrate in which a color filter is formed on the surface of a driving substrate on which a thin film transistor (TFT) is disposed, and a substrate in which an ITO (indium oxide doped with tin) electrode is formed are a liquid crystal layer. It is also possible to adopt a structure that is opposed to each other. The latter structure has the advantage that the aperture ratio can be remarkably improved, and a bright and high-definition liquid crystal display element can be obtained.
  • the color liquid crystal display device including the color filter of the present invention can include a cold cathode fluorescent tube (CCFL: Cold Cathode Fluorescent Lamp) and a backlight unit using a white LED as a light source.
  • a white LED for example, a white LED that obtains white light by color mixing by combining a red LED, a green LED, and a blue LED, a white LED that obtains white light by color mixing by combining a blue LED, a red LED, and a green phosphor, and a blue LED White LED that obtains white light by mixing colors, red LED and green light emitting phosphor, white LED that obtains white light by mixing colors of blue LED and YAG phosphor, blue LED, orange light emitting phosphor and green light emitting fluorescence
  • the color liquid crystal display device having the color filter of the present invention includes a TN (Twisted Nematic) type, an STN (Super Twisted Nematic) type, an IPS (In-Planes Switching) type, a VA (Vertical Alignment) type, and an OCB (Optic Optical).
  • TN Transmission Nematic
  • STN Super Twisted Nematic
  • IPS In-Planes Switching
  • VA Very Alignment
  • OCB Optic Optical
  • An appropriate liquid crystal mode such as a birefringence type can be applied.
  • the organic EL display device having the color filter of the present invention can have an appropriate structure, for example, the structure disclosed in Japanese Patent Application Laid-Open No. 11-307242.
  • the electronic paper including the color filter of the present invention can have an appropriate structure, for example, the structure disclosed in Japanese Patent Application Laid-Open No. 2007-41169.
  • Synthesis example 1 A flask equipped with a condenser and a stirrer was charged with 100 parts by mass of propylene glycol monomethyl ether acetate and purged with nitrogen. Heat to 80 ° C., and at the same temperature, 50 parts by mass of propylene glycol monomethyl ether acetate, 15 parts by mass of methacrylic acid, 12.5 parts by mass of 2-methacryloyloxy succinate, 10 parts by mass of styrene, 2-hydroxyethyl 2 mixed solutions of 12.5 parts by weight of methacrylate, 13 parts by weight of methyl methacrylate, 12 parts by weight of N-phenylmaleimide, 25 parts by weight of cyclohexyl methacrylate and 6 parts by weight of 2,2′-azobis (2,4-dimethylvaleronitrile) The solution was added dropwise over a period of time and polymerized for 1 hour while maintaining this temperature.
  • binder resin (B1) This binder resin is referred to as “binder resin (B1)”.
  • Example 1 Preparation of Coloring Composition 40.2 parts by mass of the colorant dispersion (A-1) as the colorant, (B) 9.9 parts by mass of the binder resin (B1) solution as the binder resin, (C) dipenta as the polymerizable compound A mixture of erythritol pentaacrylate modified with phthalic anhydride, dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd., trade name CBZ-1FC), 2 parts by weight as a photopolymerization initiator Methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one (manufactured by BASF, trade name IRGACURE907) 0.8 parts by mass, 2,4-diethylthioxanthone (manufactured by Nippon Kayaku Co.,
  • the colored composition (S-1) was applied on a soda glass substrate on which a SiO 2 film for preventing elution of sodium ions was formed using a spin coater, and then a hot plate at 90 ° C. Was pre-baked for 2 minutes to form a coating film having a thickness of 2.5 ⁇ m. Next, after cooling the substrate to room temperature, each coating film was exposed to radiation containing wavelengths of 365 nm, 405 nm, and 436 nm at an exposure amount of 400 J / m 2 through a photomask using a high-pressure mercury lamp.
  • shower development was performed for 90 seconds on these substrates by discharging a developer composed of a 0.04 mass% potassium hydroxide aqueous solution at 23 ° C. at a development pressure of 1 kgf / cm 2 (nozzle diameter: 1 mm). . Thereafter, this substrate was washed with ultrapure water, air-dried, and then post-baked in a clean oven at 200 ° C. for 30 minutes to form a dot pattern on the substrate.
  • the light resistance test coloring composition (S-1) was applied on a soda glass substrate on which a SiO 2 film for preventing elution of sodium ions was formed using a spin coater, and then applied on a hot plate at 90 ° C. Pre-baking was performed for 2 minutes to form a coating film having a thickness of 2.5 ⁇ m. Next, after cooling the substrate to room temperature, each coating film was exposed to radiation containing wavelengths of 365 nm, 405 nm, and 436 nm at an exposure amount of 400 J / m 2 through a photomask using a high-pressure mercury lamp.
  • shower development was performed for 90 seconds on these substrates by discharging a developer composed of a 0.04 mass% potassium hydroxide aqueous solution at 23 ° C. at a development pressure of 1 kgf / cm 2 (nozzle diameter: 1 mm). . Thereafter, this substrate was washed with ultrapure water, air-dried, and then post-baked in a clean oven at 200 ° C. for 30 minutes to form a dot pattern on the substrate. The obtained substrate was irradiated with a white LED showing the emission spectrum of FIG. 1 for 1000 hours. The substrate before and after the irradiation, the spectral characteristics were measured using a color analyzer (Otsuka Electronics Co., Ltd.
  • the colored composition (S-1) is a soda in which a SiO 2 film for preventing elution of sodium ions is formed on the surface, and an ITO (indium-tin oxide alloy) electrode is deposited in a predetermined shape.
  • pre-baking was performed in a clean oven at 90 ° C. for 10 minutes to form a coating film having a thickness of 2.5 ⁇ m.
  • the coating film was exposed to radiation containing wavelengths of 365 nm, 405 nm, and 436 nm at an exposure amount of 600 J / m 2 without using a photomask.
  • the substrate is immersed in a developer composed of a 0.04 mass% sodium carbonate aqueous solution at 23 ° C. for 1 minute, developed, washed with ultrapure water, air-dried, and further post-baked at 200 ° C. for 30 minutes.
  • the coating was cured to form pixels on the substrate.
  • the substrate on which this pixel is formed and the substrate on which the ITO electrode is simply deposited in a predetermined shape are bonded together with a sealing agent mixed with 0.018 mm glass beads, and then a liquid crystal MLC6608 (trade name) manufactured by Merck is used.
  • the liquid crystal cell was manufactured by pouring.
  • the liquid crystal cell was placed in a constant temperature layer at 60 ° C., and the voltage holding ratio of the liquid crystal cell was measured with a liquid crystal voltage holding ratio measuring system VHR-1A (trade name) manufactured by Toyo Technica.
  • the applied voltage at this time is a square wave of 5.0 V, and the measurement frequency is 60 Hz.
  • the voltage holding ratio is a value of (liquid crystal cell potential difference after 16.7 milliseconds / voltage immediately after application).
  • the evaluation results are shown in Table 1.
  • Examples 2 to 9 and Comparative Examples 1 to 3 Colored compositions (S-2) to (S-12) were prepared in the same manner as in Example 1 except that the colorant dispersion of the colored composition and the type of component (C) were changed as shown in Table 1. did. The obtained colored compositions (S-2) to (S-12) were evaluated in the same manner as in Example 1. The results are shown in Table 1.
  • each component is as follows, and the acid value of each (C) component was measured by the method of postscript.
  • C-1 A mixture of dipentaerythritol pentaacrylate modified with phthalic anhydride, dipentaerythritol pentaacrylate, and dipentaerythritol hexaacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd., trade name NK ester CBZ-1FC, acid value 47 mgKOH / g)
  • C-2 A mixture of dipentaerythritol pentaacrylate modified with tetrahydrophthalic anhydride, dipentaerythritol pentaacrylate, and dipentaerythritol hexaacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd., trade name NK ester CBZ-2FC, acid value 48 mgKOH) / G)
  • C-3 A mixture of hexahydrophthalate modified
  • the acid value of the component (C) was measured as follows.
  • (C) 0.5 g of component was precisely weighed to a unit of 1 mg and separated into a glass container. After diluting to 50 mL with propylene glycol monomethyl ether acetate, phenolphthalein was added, titrated with a 0.1 N ethanolic potassium hydroxide aqueous solution, and colored pink. Similarly, a blank test was performed. The acid value (unit: mgKOH / g) was calculated from the amount of component (C) and 0.1N ethanolic potassium hydroxide aqueous solution dropped in the blank test.

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JP2012103324A (ja) * 2010-11-08 2012-05-31 Toppan Printing Co Ltd 青色感光性組成物及びそれを用いたカラーフィルタ、液晶ディスプレイ及び有機ｅｌディスプレイ

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JP5251329B2 (ja) * 2008-07-22 2013-07-31 東洋インキＳｃホールディングス株式会社 カラーフィルタ用青色着色組成物、カラーフィルタおよびカラー表示装置
JP5725357B2 (ja) * 2010-09-24 2015-05-27 Dic株式会社 化合物及びカラーフィルタ

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JP2010249869A (ja) * 2009-04-10 2010-11-04 Toyo Ink Mfg Co Ltd カラーフィルタ用青色着色組成物、カラーフィルタおよびカラー表示装置
JP2012103324A (ja) * 2010-11-08 2012-05-31 Toppan Printing Co Ltd 青色感光性組成物及びそれを用いたカラーフィルタ、液晶ディスプレイ及び有機ｅｌディスプレイ
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