Classifications

• • 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
  • C09B19/00—Oxazine dyes
  • C09B19/02—Bisoxazines prepared from aminoquinones
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B69/00—Dyes not provided for by a single group of this subclass
  • C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
  • C09B69/04—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds
• • G—PHYSICS
  • G02—OPTICS
  • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
  • G02B5/00—Optical elements other than lenses
  • G02B5/20—Filters
• • 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
  • 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
  • G03F7/0005—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
  • G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
• • 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

Definitions

• the present invention relates to a colorant, a coloring composition, a color filter, and a display element. More specifically, the present invention relates to a color filter such as a transmissive or reflective color liquid crystal display element, solid-state imaging element, organic EL display element, and electronic paper. The present invention relates to a colorant suitably used for formation, a color composition containing the colorant, a color filter including a color layer containing the colorant, and a display element including the color filter.
• a color filter such as a transmissive or reflective color liquid crystal display element, solid-state imaging element, organic EL display element, and electronic paper.
• the present invention relates to a colorant suitably used for formation, a color composition containing the colorant, a color filter including a color layer containing the colorant, 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 Patent Documents 1 and 2 in which pixels of each color are obtained by irradiation (hereinafter referred to as “exposure”) and development.
• Exposure A method of forming a black matrix using a photopolymerizable composition in which carbon black is dispersed (Patent Document 3) is also known.
• a method of obtaining pixels of each color by an ink jet method using a pigment-dispersed colored resin composition is also known (Patent Document 4).
• Patent Document 4 proposes the use of a dye in which a sulfonic acid group directly bonded to a dye mother nucleus is in the form of an amine salt or a dye having a sulfonamide group introduced into a dye.
• an object of the present invention is to provide a novel colorant that is highly soluble in organic solvents, excellent in heat resistance, and useful for forming color filters and the like. Furthermore, the subject of this invention is providing the color composition containing the said coloring agent, the color filter provided with the colored layer containing the said coloring agent, and the display element which comprises the said color filter.
• the present invention provides a colorant represented by the following formula (1) (hereinafter also referred to as “the present colorant”).
• D represents a colorant matrix
• R represents a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkenylene group, a substituted or unsubstituted divalent alicyclic hydrocarbon group, or a substituted Alternatively, it represents an unsubstituted arylene group
• X + represents an organic ammonium ion
• m represents an integer of 1 or more.
• the present invention also provides a method for producing the present colorant comprising a step of reacting a dye compound having active hydrogen with a compound represented by the following formula (5) in the presence of a base.
• the present invention is a coloring composition containing (A) a coloring agent, (B) a binder resin and (C) a crosslinking agent, and (A) a coloring composition containing the above coloring agent as a coloring agent,
• the present invention provides a color filter comprising a colored layer containing the colorant 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 colorant of the present invention has high solubility in organic solvents and excellent heat resistance. And if the coloring composition containing the coloring agent of this invention is used, the color filter which has each color pixel with a high contrast can be obtained.
• the colorant of the present invention includes various color filters including, for example, a color filter for a color liquid crystal display element, a color filter for color separation of a solid-state image sensor, a color filter for an organic EL display element, and a color filter for electronic paper. Can be used very suitably. Further, the colorant of the present invention can be suitably used for an electrophoretic display element. Furthermore, the colorant of the present invention can also be used as a pigment derivative type pigment dispersant.
• the alkylene group may be linear or branched, and examples thereof include an alkylene group having 2 to 20 carbon atoms. Specifically, ethylene group, propylene group, trimethylene group, tetramethylene group, butane-1,3-diyl group, pentamethylene group, pentane-1,3-diyl group, pentane-1,4-diyl group, hexane -1,4-diyl group, hexane-1,5-diyl group, 4,4-dimethylpentane-1,3-diyl group, dodecane-1,4-diyl group and the like.
• the alkylene group may have a substituent, and examples of the substituent include a halo group, and among them, a fluoro group is preferable.
• the alkenylene group may be linear or branched, and examples thereof include an alkenylene group having 3 to 6 carbon atoms. Specifically, 1-propene-1,3-diyl group, but-1-ene-1,3-diyl group, penta-1-ene-1,3-diyl group, hexa-1-ene-1, 3-diyl group and the like can be mentioned.
• the alkenylene group may have a substituent, and examples of the substituent include a halo group.
• examples of the divalent alicyclic hydrocarbon group include a bicyclo [2.2.1] heptane-2,6-diyl group.
• the divalent alicyclic hydrocarbon group may have a substituent, and examples of the substituent include a hydroxyl group.
• examples of the arylene group include a naphthalene-1,8-diyl group.
• the arylene group may have a substituent, and examples of the substituent include an alkoxy group, a halo group, a nitro group, a cyano group, and a trifluoromethyl group.
• R is preferably an alkylene group, a fluorinated alkylene group or an alkenylene group, and more preferably an alkylene group having 2 to 5 carbon atoms, a fluorinated alkylene group having 2 to 5 carbon atoms or an alkenylene group having 3 to 6 carbon atoms. preferable.
• D represents a colorant matrix. From the viewpoint of ease of production of the present colorant, D represents —NHCO—, —CONHCO—, —OH, —NH 2 , —NH—, —COCH 2 CO—, It is preferably a residue obtained by removing one or more active hydrogens from a dye compound having a group having active hydrogens such as —COOH and —SH.
• m can be appropriately selected according to the type of the present colorant as long as it is an integer of 1 or more, but is preferably an integer of 1 to 6 from the viewpoint of ease of production of the present colorant. An integer of 4 is more preferable.
• Examples of the dye compound having a group having active hydrogen include a compound represented by the following formula (6), a compound represented by the following formula (7), a compound represented by the following formula (8), and the following compound: Mention may be made of the compounds shown in groups ak.
• R 1 to R 4 each independently represent a hydrogen atom, a halo group, an alkyl group, an alkoxy group, an alkyl-substituted amino group, a trifluoromethyl group, or a nitro group.
• R 1 to R 2 each independently represent a hydrogen atom, a halo group, an alkyl group, an alkoxy group, an alkyl-substituted amino group, a trifluoromethyl group, or a nitro group.
• a hydrogen atom and an alkyl group are preferable, and a hydrogen atom is particularly preferable.
• R 3 to R 4 each independently represent a hydrogen atom, a halo group, an alkyl group, an alkoxy group, an alkyl-substituted amino group, a trifluoromethyl group or a nitro group. Of these, a halo group is preferred.
• halo group examples include fluorine, chlorine, bromine and iodine. Among them, chlorine is preferable.
• the number of carbon atoms of the alkyl group constituting R 1 to R 4 and the alkyl group constituting the alkyl-substituted amino group is preferably 1-20, and more preferably 1-12.
• the alkyl-substituted amino group may be mono-substituted or di-substituted.
• the number of carbon atoms of the alkoxy group in R 1 to R 4 is preferably 1 to 8, and more preferably 1 to 4.
• the alkyl group and alkoxy group may be linear or branched.
• D is a residue obtained by removing one or more active hydrogens from a dye compound having —NHCO—, —CONHCO—, particularly —NHCO—, from the viewpoint of solubility in organic solvents and heat resistance. It is preferable. That is, as this coloring agent, what has a structure represented by following formula (4) is preferable.
• R and X + are synonymous with R and X + in Formula (1) above, and “*” indicates a bond. ]
• X + is not particularly limited as long as it is an organic ammonium ion, but is preferably represented by the following formula (2) or the following formula (3) from the viewpoint of solubility in an organic solvent and heat resistance.
• Q 1 to Q 5 each independently represent a hydrogen atom, a substituted or unsubstituted hydrocarbon group, a phenacyl group or a heterocyclic group
• Q 6 represents a hydrogen atom
• An atom, a halo group, a substituted or unsubstituted hydrocarbon group, an alkoxycarbonyl group, a carbamoyl group, or a benzyloxy group is shown.
• at least one of Q 1 to Q 4 represents a substituted or unsubstituted hydrocarbon group.
• the hydrocarbon group includes, for example, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, carbon Examples thereof include an aralkyl group of 7 to 20.
• Examples of the aliphatic hydrocarbon group having 1 to 20 carbon atoms include an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, and an alkynyl group having 2 to 20 carbon atoms.
• Examples of the alicyclic hydrocarbon group having 3 to 20 carbon atoms include a cycloalkyl group having 3 to 8 carbon atoms and a cycloalkenyl group having 3 to 8 carbon atoms.
• the alkyl group, alkenyl group and alkynyl group may be linear or branched, and the alkenyl group and alkynyl group may have an unsaturated bond in the molecule or at the terminal.
• Examples of the aryl group having 6 to 20 carbon atoms include a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, and a biphenylene group.
• Examples of the aralkyl group having 7 to 20 carbon atoms include benzyl group, phenethyl group, trityl group, alkylene (preferably C 1-6 alkylene) -phenylene-alkylene (preferably C 1-6 alkylene) group, alkylene (preferably C And 1-6 alkylene) -biphenylene-alkylene (preferably C 1-6 alkylene) group.
• C 1-6 in the present specification means having 1 to 6 carbon atoms.
• These hydrocarbon groups may have a substituent.
• substituents include a hydroxyl group, an alkoxy group, a halo group, a nitro group, a cyano group, an amide group, a sulfonic acid group, and an alkyl (preferably C 1-6 alkyl) -carbonyl group, aryl (preferably C 6-14 aryl) -carbonyl group and the like can be mentioned.
• the position and number of these substituents are arbitrary, and when they have two or more substituents, the substituents may be the same or different.
• C 6-14 in this specification means that the number of carbon atoms is 6-14 .
• the heterocyclic group is a monocycle formed by combining a carbon atom and at least one atom selected from a nitrogen atom, an oxygen atom and a sulfur atom (preferably 3 to And groups derived from an 8-membered ring, more preferably a 5- to 6-membered ring.
• alicyclic heterocyclic groups such as pyrrolidinyl group, imidazolidinyl group, pyrazolidinyl group, piperidyl group, piperidino group, piperazinyl group, homopyrerazinyl group, morpholinyl group, theomorpholinyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl Group, quinolyl group, isoquinolyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, thienyl group, furyl group, pyranyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, triazoyl group, tetrazolyl group, thiazolyl group, oxazolyl group, indolyl group, Aromatic heterocyclic groups such as indazolyl group, benzoimidazolyl group, and
• a hydrogen atom or a substituted or unsubstituted hydrocarbon group is preferable.
• the hydrocarbon group an aliphatic hydrocarbon group having 1 to 20 carbon atoms and an alicyclic hydrocarbon group having 3 to 20 carbon atoms are preferable, an alkyl group having 1 to 20 carbon atoms, and a cyclohexane having 3 to 8 carbon atoms.
• An alkyl group is more preferable, and an alkyl group having 1 to 20 carbon atoms is particularly preferable.
• Q 1 to Q 4 represents a substituted or unsubstituted hydrocarbon group
• examples of the hydrocarbon group include aliphatic hydrocarbon groups having 1 to 20 carbon atoms, and 3 to 20 carbon atoms.
• the alicyclic hydrocarbon group is preferably an alkyl group having 1 to 20 carbon atoms, more preferably a cycloalkyl group having 3 to 8 carbon atoms, and particularly preferably an alkyl group having 1 to 20 carbon atoms.
• alkoxy in the alkoxycarbonyl group may be linear or branched, but preferably has 1 to 6 carbon atoms.
• Q 6 is preferably a hydrogen atom or a substituted or unsubstituted hydrocarbon group, particularly preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
• X + represented by the above formula (2) is preferably a mono-, di-, tri- or tetraalkylammonium ion, particularly preferably a tetraalkylammonium ion.
• X + represented by the above formula (3) includes, for example, pyridinium ion, alkyl-substituted pyridinium ion, 1-alkylpyridinium ion, 1-alkyl-halo-substituted pyridinium ion, 1-alkyl-alkoxycarbonyl-substituted pyridinium ion, Examples thereof include 1-phenacylpyridinium ion, 1-alkyl-carbamoyl-substituted pyridinium ion, and 1-alkyl-benzyloxy-substituted pyridinium ion.
• the colorant includes, for example, a step of reacting a dye compound having active hydrogen with a compound represented by the following formula (5) in the presence of a base (hereinafter also referred to as “step 1”), and the resulting dye.
• the compound can be produced by subjecting the sulfonate salt of the compound to a salt exchange reaction with an organic quaternary ammonium salt (hereinafter also referred to as “step 2”).
• the dye compound having active hydrogen used in Step 1 may be synthesized by a known method or may be a commercially available product.
• a commercially available product for example, in the compound represented by the above formula (6), Z is an ethoxy group and R 1 and R 2 are hydrogen atoms (CI Pigment Violet 37), and the above formula ( The compound represented by 7) wherein R 3 and R 4 are chlorine atoms (CI Pigment Red 254) can be obtained from Ciba Specialty Chemicals.
• Examples of the base used in Step 1 include potassium carbonate, sodium bicarbonate, sodium hydroxide, potassium hydroxide, sodium methylate, potassium t-butoxide, triethylamine, DBU, sodium hydride and the like. .
• R is preferably an alkylene group, a fluorinated alkylene group or an alkenylene group.
• Examples of such a compound include compounds represented by the following formula (5-1). .
• R a represents a methylene group or alkylene group which may have a halo group, or an alkenylene group
• R b represents a hydrogen atom or an alkyl group which may have a halo group.
• R c represents a hydrogen atom or a halo group.
• the alkylene group preferably has a carbon number of 2-4 in the R a, alkenylene group in R a is preferably from 2 carbon atoms, the alkyl group in R b is preferably having a carbon number of 1-3.
• the total carbon number of R a and R b is preferably 1 to 5.
• Specific examples of the compound represented by the above formula (5) include 1,2-ethane sultone, 1,3-propane sultone, 1,4-butane sultone, 2,4-butane sultone, 1,5-pentane sultone, , 5-pentane sultone, 3,5-pentane sultone, 3,6-hexane sultone, 2,6-hexane sultone, 2,2-dimethyl-3,5-pentane sultone, 9,12-dodecane sultone, 1,3 -Propene sultone, perfluoro-1,2-ethane sultone, perfluoro-2,3-propane sultone, perfluoro-3,4-butane sultone, 1,8-naphtho sultone, 5-hydroxy-2,6-bicyclo [2. 2.1] heptane sultone (5-hydroxy-3-oxa-2-Chiatori
• the compound represented by the above formula (5) can be produced by a known method, for example, a method described in JP-A-5-43572, JP-A-2007-31355, etc. May be used.
• Step 1 is preferably performed in a solvent.
• the solvent include amides such as N, N-dimethylformamide and N, N-dimethylacetamide, pyrrolidones such as N-methylpyrrolidone, N, N
• amides such as N, N-dimethylformamide and N, N-dimethylacetamide
• pyrrolidones such as N-methylpyrrolidone
• N N
• imidazolidinone such as' -dimethylimidazolidinone
• nitrile such as acetonitrile
• ether such as tetrahydrofuran.
• the reaction temperature is, for example, 20 to 150 ° C.
• the reaction time is, for example, 30 minutes to 48 hours.
• Examples of the organic quaternary ammonium salt used in Step 2 include tetraethylammonium halide, tetrabutylammonium halide, dimethyl (dioctadecyl) ammonium halide, tetrahexylammonium halide, tributyl (methyl) ammonium halide, tetradodecylammonium halide, tetra Octyl ammonium halide, trimethyl (hexadecyl) ammonium halide, trioctyl (methyl) ammonium halide, tetraisopentyl ammonium halide, 1-butyl-3-methylpyridinium halide, 1-butyl-4-methylpyridinium halide, 1-butylpyridinium halide, 1-dodecylpyridinium halide, 1-ethyl-3- (hydroxymethyl) pyridinium ethyl
• the above step 2 is also preferably carried out in a solvent.
• the solvent include amides such as N, N-dimethylformamide and N, N-dimethylacetamide, pyrrolidones such as N-methylpyrrolidone, N, N′— Examples thereof include imidazolidinone such as dimethylimidazolidinone, nitrile such as acetonitrile, ether such as tetrahydrofuran, alcohol such as methanol and ethanol, and ketone such as acetone. These solvents may be used alone or in admixture of two or more.
• the reaction temperature is, for example, 20 to 70 ° C.
• the reaction time is, for example, 30 minutes to 12 hours.
• the reaction system can be used by appropriately combining ordinary purification means such as filtration, washing, drying, concentration, reprecipitation, centrifugation, extraction with various solvents, and chromatography.
• the compound can be isolated.
• finish of the process 1 you may use for a process 2 without isolating a target compound.
• a compound in which a sulfonic acid group is introduced into the dye compound via an alkylene group or a compound in which a sulfonimide group is introduced into the dye compound via an alkylene group can also be produced.
• the compound thus obtained can also be used as a colorant.
• the colorant thus obtained is soluble in various organic solvents such as ketones such as cyclohexanone as shown in Examples below, and has a 5% mass reduction temperature in TG-DTA analysis. Can have excellent heat resistance of 300 ° C. or higher.
• colored composition the components of the colored composition of the present invention (hereinafter also simply referred to as “colored composition”) will be described.
• the coloring composition of this invention contains this coloring agent as (A) coloring agent.
• This coloring agent can be used individually or in mixture of 2 or more types.
• a colorant other than the present colorant can also be contained as the colorant (A).
• Such a colorant is not particularly limited as long as it has colorability, and colors and materials can be appropriately selected according to the use of the color filter.
• any of pigments, dyes and natural pigments can be used. However, since color filters are required to have high color purity, brightness, contrast, etc., A dye is preferred.
• the pigment may be either an organic pigment or an inorganic pigment, and examples of the organic pigment include compounds classified as pigments in the color index (CI; issued by The Society of Dyer's and Colorists). . Specific examples include those with the following color index (CI) names.
• CI color index
• the inorganic pigment examples include, for example, titanium oxide, barium sulfate, calcium carbonate, zinc white, lead sulfate, yellow lead, zinc yellow, red bean (red iron (III) oxide), cadmium red, ultramarine blue, bitumen, and chromium oxide.
• examples include green, cobalt green, amber, titanium black, synthetic iron black, and carbon black.
• 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 is preferably used by refining primary particles by so-called salt milling.
• a salt milling method for example, a method disclosed in Japanese Patent Application Laid-Open No. 08-179111 can be employed.
• the dye can be appropriately selected from various oil-soluble dyes, direct dyes, acid dyes, metal complex dyes, and the like.
• CI color index
• colorants can be used alone or in admixture of two or more.
• 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. 5 to 60% by mass. Solid content here is components other than the solvent mentioned later.
• a pigment when used as another colorant, it can be used together with a dispersant and a dispersion aid as desired.
• a dispersing agent for example, an appropriate dispersing agent such as a cationic type, an anionic type, or a nonionic type can be used, and a polymer dispersing agent is preferable.
• Such dispersants are commercially available.
• acrylic dispersants such as Disperbyk-2000, Disperbyk-2001, BYK-LPN6919, BYK-LPN21116, BYK-LPN21324 (above, BYK Corporation (BYK) And the like as urethane dispersants such as Disperbyk-161, Disperbyk-162, Disperbyk-165, Disperbyk-167, Disperbyk-170, Disperbyk-182 (above, manufactured by BYK Chemy (BYK)), Solsperse 76500 (Lubrisol) Etc.) as a polyethyleneimine-based dispersant, Solsperse 24000 (manufactured by Lubrizol Co., Ltd.), etc.
• the dispersion aid include pigment derivatives, and specific examples include copper phthalocyanine, diketopyrrolopyrrole, and sulfonic acid derivatives of quinophthalone.
• the contents of the dispersant and the dispersion aid can be appropriately determined within a range that does not impair the object of the present invention.
• the coloring composition of the present invention contains (B) a binder resin.
• a binder resin is not particularly limited, but is preferably a resin having an acidic functional group such as a carboxyl group or a phenolic hydroxyl group.
• a polymer having a carboxyl group hereinafter referred to as “carboxyl group-containing polymer”.
• carboxyl group-containing polymer an ethylenically unsaturated monomer having one or more carboxyl groups (hereinafter referred to as “unsaturated monomer”).
• (B1) ) and other copolymerizable ethylenically unsaturated monomers hereinafter 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-equivalent weight average molecular weight (hereinafter also referred to as “Mw”) measured by GPC (elution solvent: tetrahydrofuran), usually 1,000 to 100,000, preferably 3,000. ⁇ 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-equivalent weight average molecular weight measured by GPC (elution solvent: tetrahydrofuran)
• the ratio (Mw / Mn) between the Mw of the binder resin in the present invention and the number average molecular weight in terms of polystyrene (hereinafter also referred to as “Mn”) measured by GPC (elution solvent: tetrahydrofuran) is preferably 1. 0.0 to 5.0, more preferably 1.0 to 3.0.
• 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 mass, preferably 20 to 500 parts by mass with respect to 100 parts by mass of the (A) colorant. 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.
• (C) a crosslinking agent refers to a compound having two or more polymerizable groups.
• the polymerizable group include an ethylenically unsaturated group, an oxiranyl group, an oxetanyl group, and an N-alkoxymethylamino group.
• the (C) crosslinking agent is preferably a compound having two or more (meth) acryloyl groups or a compound having two or more N-alkoxymethylamino groups.
• the compound having two or more (meth) acryloyl groups include a polyfunctional (meth) acrylate obtained by reacting an aliphatic polyhydroxy compound and (meth) acrylic acid, a caprolactone-modified polyfunctional ( (Meth) acrylate, alkylene oxide-modified polyfunctional (meth) acrylate, hydroxyl-functional (meth) acrylate and polyfunctional isocyanate obtained by reacting with polyfunctional isocyanate, hydroxyl-functional (meth) acrylate and acid
• the polyfunctional (meth) acrylate which has a carboxyl group obtained by making an anhydride react can be mentioned.
• 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.
• Examples of the hydroxyl group-containing (meth) acrylate include 2-hydroxyethyl (meth) acrylate, trimethylolpropane di (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, and glycerol diester. A methacrylate etc. can be mentioned.
• Examples of the polyfunctional isocyanate include tolylene diisocyanate, hexamethylene diisocyanate, diphenylmethylene diisocyanate, and isophorone diisocyanate.
• acid anhydrides examples include succinic anhydride, maleic anhydride, glutaric anhydride, itaconic anhydride, phthalic anhydride, dibasic acid anhydrides such as hexahydrophthalic anhydride, pyromellitic anhydride, biphenyltetracarboxylic acid.
• acid anhydrides include succinic anhydride, maleic anhydride, glutaric anhydride, itaconic anhydride, phthalic anhydride, dibasic acid anhydrides such as hexahydrophthalic anhydride, pyromellitic anhydride, biphenyltetracarboxylic acid.
• dianhydrides and tetrabasic acid dianhydrides such as benzophenone tetracarboxylic dianhydride.
• 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 alkylene oxide-modified polyfunctional (meth) acrylate include ethylene oxide of bisphenol A and / or propylene oxide modified di (meth) acrylate, ethylene oxide of isocyanuric acid and / or propylene oxide modified tri (meth) acrylate, tri Ethylene oxide and / or propylene oxide modified tri (meth) acrylate of methylolpropane, ethylene oxide and / or propylene oxide modified tri (meth) acrylate of pentaerythritol, ethylene oxide and / or propylene oxide modified tetra (meth) acrylate of pentaerythritol Dipentaerythritol ethylene oxide and / or propylene oxide modified penta (meth) acrylate, di It can be
• 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.
• N-alkoxymethylamino groups include N, N, N ′, N ′, N ′′, N ′′ -hexa (alkoxymethyl) melamine, N, N, N ′, N Examples include '-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, Polyfunctional urethane (meth) acrylate, polyfunctional (meth) acrylate having a 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, pentaerythritol triacrylate, dipentaerythritol pentaacrylate, dipenta Erythritol hexaacrylate is a compound obtained by reacting pentaerythritol triacrylate and succinic anhydride, among polyfunctional (meth) acrylates having a carboxyl group, and obtained by reacting dipentaerythritol pentaacrylate and succinic anhydride.
• the compound is particularly preferable in that the strength of the colored layer is high, the surface smoothness of the colored layer is excellent, and background stains and film residues are hardly generated on the unexposed substrate and the light shielding layer.
• (C) the crosslinking agent can be used alone or in admixture of two or more.
• the content of the (C) crosslinking agent is preferably 10 to 1,000 parts by mass, particularly preferably 20 to 500 parts by mass, with respect to 100 parts by mass of the (A) colorant.
• the content of the polyfunctional monomer is too small, sufficient curability may not be obtained.
• the content of the polyfunctional monomer is too large, when the color composition of the present invention is imparted with alkali developability, the alkali developability is lowered, and on the unexposed portion of the substrate or the light shielding layer. There is a tendency that dirt, film residue, etc. are likely to occur.
• the coloring composition of the present invention can contain (D) a photopolymerization initiator. Thereby, radiation sensitivity can be provided to a coloring composition.
• the (D) photopolymerization initiator used in the present invention generates an active species capable of initiating the polymerization of the above (C) crosslinking agent by exposure to radiation such as visible light, ultraviolet light, far ultraviolet light, electron beam, and X-ray. A compound.
• 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 and the like.
• the photopolymerization initiators can be used alone or in admixture of two or more.
• the photopolymerization initiator is preferably 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, and the like.
• 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.
• Ethyl aminobenzoate 2-ethylhexyl 4-dimethylaminobenzoate, 2,5-bis (4-diethylaminobenzal) cyclohexanone, 7-diethylamino-3- (4-diethylaminobenzoyl) coumarin, 4- (diethylamino) chalcone, etc. Can be mentioned.
• the content of the photopolymerization initiator is preferably 0.01 to 120 parts by mass, particularly preferably 1 to 100 parts by mass, with respect to 100 parts by mass of the (C) cross-linking agent.
• the content of the photopolymerization initiator is too small, curing by exposure may be insufficient.
• 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.
• 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
• propylene glycol monomethyl ether propylene glycol monoethyl ether, propylene glycol monomethyl ether acetate, 3-methoxybutyl acetate, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether from the viewpoint of solubility, pigment dispersibility, coatability, etc.
• a solvent can be used individually or in mixture of 2 or more types.
• the content of the solvent is not particularly limited, but the total concentration of each component excluding the solvent of the colored composition is 5 to 50 from the viewpoint of the coating property and stability of the obtained colored composition.
• An amount of mass% is preferable, and an amount of 10 to 40 mass% is particularly preferable.
• 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 Dimethoxysilane, 3-chloropro Adhesion promoters such as rutrime
• the color filter of the present invention comprises a colored layer containing the present colorant.
• a light shielding layer (black matrix) is formed on the surface of the substrate so as to divide a portion where pixels are formed, if necessary.
• pre-baking is performed to evaporate the solvent, thereby forming a coating film.
• post-baking is performed to form a pixel array in which red pixel patterns are arranged in a predetermined arrangement.
• each colored radiation-sensitive composition of green or blue is used, and each colored radiation-sensitive composition is applied, pre-baked, exposed, developed, and post-baked in the same manner as described above, so that the green pixel array and blue Are sequentially formed on the same substrate.
• 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.
• 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. Using the radiation-sensitive composition, it can be formed in the same manner as in the case of forming the pixel.
• Examples of the substrate used when forming the color filter 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, 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 8.0 ⁇ m, preferably 1.2 to 5.0 ⁇ 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 of the light source include a laser light source such as an argon ion laser, a YAG laser, a XeCl excimer laser, and a nitrogen laser. Radiation having a wavelength in the range of 190 to 450 nm is preferable. In general, the exposure dose of radiation is preferably 10 to 10,000 J / m 2 .
• alkali developer examples 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 surfactant or the like can be added to the alkaline developer.
• it is usually washed with water after alkali development.
• a shower development method As the 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.
• the development conditions are preferably 5 to 300 seconds at room temperature.
• the post-baking conditions are usually about 180 to 280 ° C. and about 10 to 60 minutes.
• the film thickness of the pixel thus formed is usually 0.5 to 5.0 ⁇ m, preferably 1.0 to 3.0 ⁇ 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. .
• this method first, a partition having a light shielding function is formed on the surface of the substrate.
• pre-baking is performed to evaporate the solvent.
• this coating film is exposed as necessary and then cured by post-baking to form a red pixel pattern.
• a green pixel pattern and a blue pixel pattern are sequentially formed on the same substrate in the same manner as described above. Thereby, a color filter in which pixel patterns 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.
• 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 for forming the color filter, the light source for radiation, and the pre-baking and post-baking methods and conditions are the same as those 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 as necessary on the pixel pattern thus obtained, 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 colored radiation-sensitive 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.
• 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 imaging 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.
• Examples of the display element include a color liquid crystal display element, an organic EL display element, and electronic paper.
• the color liquid crystal display device having the color filter of the present invention 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.
• 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 mixing red LED, green LED, and blue LED, a white LED that obtains white light by mixing blue LED, red LED, and green light emitting phosphor, blue A white LED that obtains white light by mixing colors, a white LED that obtains white light by mixing colors of a blue LED and YAG phosphor, a blue LED, an orange light emitting phosphor, and green light emission
• a white LED that obtains white light by color mixing by combining phosphors a white LED that obtains white light by color mixing by combining an ultraviolet LED, a red light emitting phosphor, a green light emitting phosphor, and a blue light emitting phosphor can be exemplified.
• 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 An appropriate liquid crystal mode such as a birefringence type can be applied.
• 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.
• Example 1 Synthesis and evaluation of compound (ix) described in the above specific example
• Sodium hydride 0.3 g, C.I. I. 1.63 g of Pigment Violet 37 (hereinafter referred to as “PV-37”) and 20 mL of dimethylformamide were mixed and stirred at room temperature for 2 hours, and further 1.45 g of 1,4-butane sultone was added and stirred for 12 hours. Thereafter, the reaction solution was filtered through Celite, and the filtrate was reprecipitated with 300 mL of acetone. The obtained solid was washed with acetone to obtain 1.5 g of a blue solid.
• TG-DTA thermogravimetric-differential thermal simultaneous measurement analysis of Compound A
• Example 2 In Example 1, C.I. I. A colorant was synthesized in the same manner as in Example 1 except that CI Pigment Red 254 (a compound in which both R 3 and R 4 in the above formula (7) are chlorine atoms) was used, and 1 H-NMR (solvent: Deuterated chloroform) was confirmed to be the target compound.
• CI Pigment Red 254 a compound in which both R 3 and R 4 in the above formula (7) are chlorine atoms
• 1 H-NMR solvent: Deuterated chloroform
• Example 3 In Example 1, C.I. I. In place of Pigment Violet 37, C.I. I. Pigment Yellow 128 (compound represented by the following formula), 1-ethyl-pyridinium chloride in place of dimethyl dioctadecyl ammonium chloride, except for using each color are synthesized in the same manner as in Example 1, 1 H It was confirmed by NMR (solvent: deuterated chloroform) that the compound was the objective compound.
• the colorants obtained in Examples 2 to 3 were all dissolved in cyclohexanone by 10% by mass or more. Further, the 5% mass reduction temperature based on TG-DTA of the colorants obtained in Examples 2 to 3 was 250 ° C. or more.
• Preparation Example 2 As a coloring agent, C.I. I. Pigment Blue 15: 6 instead of C.I. I. A pigment dispersion (A-2) was prepared in the same manner as in Preparation Example 1, except that CI Pigment Violet 23 was used.
• a dye solution A was prepared by mixing 5 parts by mass of Compound A as a colorant and 95 parts by mass of propylene glycol monomethyl ether acetate as a solvent.
• binder resin (B1) This binder resin is referred to as “binder resin (B1)”.
• Example 4 13.6 parts by mass of pigment dispersion (A-1), 27.2 parts by mass of dye solution A, 16.1 parts by mass of binder resin (B1) solution as a binder resin, and M-402 manufactured by Toagosei Co., Ltd. as a crosslinking agent (Mixture of dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate) 5.5 parts by mass and MW-30 (N, N, N ′, N ′, N ′′, N ′′ -hexa (methoxy) manufactured by Sanwa Chemical Co., Ltd.
• Methyl) melamine as a main component, weight average degree of polymerization 1.3) 2.4 parts by mass, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one as a photopolymerization initiator ( Ciba Specialty Chemicals, trade name IRGACURE 369) 2.2 parts by mass, and propylene glycol monomethyl ether acetate as a solvent Combined with a solid content concentration of 20 mass% of the coloring composition (CR1) was prepared.
• the coloring composition (CR1) was applied on a glass substrate using a spin coater, and then pre-baked on an 80 ° C. hot plate for 10 minutes to form a coating film. Three coating films having different film thicknesses were formed by the same operation while changing the rotation speed of the spin coater. Next, after cooling these substrates to room temperature, a high-pressure mercury lamp is used, and a radiation containing each wavelength of 365 nm, 405 nm, and 436 nm is applied to each coating film without using a photomask at an exposure dose of 2,000 J / m 2 . And exposed.
• 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 230 ° C. for 30 minutes to form a cured film for evaluation.
• the substrate on which the cured film is formed is sandwiched between two deflection plates, and the front side deflection plate is rotated while irradiating with a fluorescent lamp (wavelength range: 380 to 780 nm) from the rear side to obtain a luminance meter LS-100 (Minolta Co.
• the maximum value and the minimum value of the light intensity transmitted through (made by)) were measured.
• the evaluation results are shown in Table 1.
• Comparative Example 2 18.1 parts by mass of the pigment dispersion (A-1), 4.5 parts by mass of the pigment dispersion (A-2), 16.1 parts by mass of the binder resin (B1) solution as the binder resin, and Toagosei Co., Ltd.

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