WO2019132328A1 - Composition de résine durcissable rouge, filtre coloré, et dispositif d'affichage - Google Patents
Composition de résine durcissable rouge, filtre coloré, et dispositif d'affichage Download PDFInfo
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- WO2019132328A1 WO2019132328A1 PCT/KR2018/015769 KR2018015769W WO2019132328A1 WO 2019132328 A1 WO2019132328 A1 WO 2019132328A1 KR 2018015769 W KR2018015769 W KR 2018015769W WO 2019132328 A1 WO2019132328 A1 WO 2019132328A1
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- JDJICLDFLREZAY-UHFFFAOYSA-N CC(C)(C)C(C(NC1=N)=N)=C1c(cccc1)c1F Chemical compound CC(C)(C)C(C(NC1=N)=N)=C1c(cccc1)c1F JDJICLDFLREZAY-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D17/00—Pigment pastes, e.g. for mixing in paints
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
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- G—PHYSICS
- 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
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- 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
- G02F1/133509—Filters, e.g. light shielding masks
- G02F1/133514—Colour filters
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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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
- G03F7/0005—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
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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
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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
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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
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
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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
- G03F7/09—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
Definitions
- the present invention relates to a red-curable resin composition, a color filter, and a display device.
- Display devices such as liquid crystal display devices, electroluminescence display devices, and plasma displays, and color filters used in solid-state image pickup devices such as CCDs and CMOS sensors are made of a colored curable resin composition.
- a color-curable resin composition a composition containing C. I. Pigment Red 177 as a colorant is known (Patent Document 1: JP-A-2004-341245).
- a colorant comprising a colorant, a resin, a polymerizable compound and a polymerization initiator
- the coloring agent comprises a tetraazaporphyrin compound and a red dye.
- a display device comprising the color filter according to [2].
- the red curable resin composition of the present invention it is possible to form a color filter having a high color (high chroma) and a thin film.
- the red curable resin composition of the present invention is a red curable resin composition comprising a colorant (hereinafter sometimes referred to as a colorant (A)), a resin (hereinafter sometimes referred to as a resin (B) )), And a polymerization initiator (hereinafter sometimes referred to as a polymerization initiator (D)).
- a colorant hereinafter sometimes referred to as a colorant (A)
- a resin hereinafter sometimes referred to as a resin (B)
- D polymerization initiator
- the red curable resin composition of the present invention preferably further contains a solvent (hereinafter, sometimes referred to as a solvent (E)).
- a solvent hereinafter, sometimes referred to as a solvent (E)
- the red curable resin composition of the present invention may further contain a leveling agent.
- the colorant (A) includes a tetraazaporphyrin compound and a red pigment.
- the tetraazaporphyrin compound is a compound having a tetraaza porphyrin skeleton in the molecule.
- the tetraazaporphyrin compound is a salt, it may form a salt with an optional cation or anion.
- a compound represented by the formula (1) (hereinafter sometimes referred to as a compound (1)) is preferable.
- R 1a to R 1d and R 2a to R 2d each independently represent a saturated hydrocarbon group which may have a substituent or an aryl group which may have a substituent.
- x 1 or 2;
- M1 represents a divalent metal atom, a substituted metal atom or a metal oxide metal.
- M1 represents a hydrogen atom or a monovalent metal atom.
- R 1a to R 1d and R 2a to R 2d are groups bonded to the tetraazaporphyrin skeleton.
- R 1a to R 1d may be the same or different and are preferably the same and R 2a to R 2d may be the same or different and are preferably the same. It is more preferable that R 1a to R 1d are the same and R 2a to R 2d are the same.
- Examples of the saturated hydrocarbon group represented by R 1a to R 1d and R 2a to R 2d include a methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n- A straight chain alkyl group such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a n-butyl group, a n-butyl group, Butyl group, 2-methylbutyl group, 1-methylbutyl group, neopentyl group, 1,2-dimethylpropyl group, 1,1-dimethylpropyl group, 4-methylpentyl group Methylpentyl, 1-methylpentyl, 3,3-dimethylbutyl, 2,3-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl Dimethylbutyl group, a 1-ethylbutyl group
- the number of carbon atoms in the saturated hydrocarbon group is preferably from 1 to 20, more preferably from 1 to 15, still more preferably from 1 to 10, still more preferably from 1 to 5.
- an alkyl group having 1 to 10 carbon atoms is preferable, and an alkyl group having 1 to 5 carbon atoms is more preferable.
- a halogen atom is preferable.
- the saturated hydrocarbon group having a halogen atom include a chloromethyl group, a dichloromethyl group, a fluoromethyl group, a trifluoromethyl group, a pentafluoroethyl group, a nonafluorobutyl group, a perfluorocyclobutyl group, a perfluorocyclopentyl group, .
- Examples of the aryl group represented by R 1a to R 1d and R 2a to R 2d include a phenyl group, a methylphenyl group, a dimethylphenyl group, a trimethylphenyl group, a naphthyl group and a methylnaphthyl group.
- Examples of the substituent which the aryl group may have include a nitro group, a cyano group, a halogen atom (preferably a fluorine atom, a chlorine atom or a bromine atom), a hydroxyl group, a carboxyl group, an alkoxy group having 1 to 8 carbon atoms, And an amino group which may be substituted with an alkyl group of 1 to 20 carbon atoms.
- Examples of the aryl group having a substituent include a fluorophenyl group, a difluorophenyl group, a trifluorophenyl group, a tetrafluorophenyl group, a pentafluorophenyl group, a chlorophenyl group, a dichlorophenyl group, a trichlorophenyl group, a tetrachlorophenyl group, And examples thereof include a triphenylmethyl group, a triphenylmethyl group, a triphenylmethylphenyl group, a triphenylmethylphenyl group, a triphenylmethylphenyl group, a triphenylmethylphenyl group, a triphenylmethylphenyl group, a triphenylmethylphenyl group, a triphenylmethylphenyl group, a triphenylmethylphenyl group, a triphenylmethylphenyl group, a triphenylmethyl
- the carbon number of the aryl group is, for example, 6 to 20, preferably 6 to 18, more preferably 6 to 15, and still more preferably 6 to 10.
- aryl group which may have a substituent, an unsubstituted aryl group or an aryl group substituted with a halogen atom is preferable.
- Each of R & lt ; 1a > to R < 1d > is preferably a saturated hydrocarbon group having 1 to 10 carbon atoms, which may have a substituent, and more preferably each independently a group having 1 to 10 carbon atoms, Chain or branched-chain alkyl group, more preferably each independently, a straight or branched alkyl group having 1 to 5 carbon atoms which may have a substituent. It is particularly preferable that each of R 1a to R 1d is a tert-butyl group.
- Each of R 2a to R 2d is preferably an aryl group having 6 to 20 carbon atoms, which may have a substituent, and more preferably each independently, an aryl group having 6 to 20 carbon atoms and having a substituent, More preferably, each independently is an aryl group having 6 to 20 carbon atoms substituted with a halogen atom, and particularly preferably an aryl group having 6 to 20 carbon atoms substituted with a fluorine atom. It is particularly preferable that R 2a to R 2d are 2-fluorophenyl groups.
- Examples of the monovalent metal atom represented by M1 when x is 2 include alkali metal atoms such as Na, K and Li. In this case,> N- and -N ⁇ in the formula (1) are bonded to each monovalent metal atom without intermediate connection.
- Examples of the divalent metal atom showing M1 when x is 1 include Cu, Zn, Fe, Co, Ni, Ru, Rh, Pd, Pt, Mn, Mg, Ti, Be, Ca, Ba, Cd, Hg, Pb And Sn.
- a compound wherein x is 1 and M 1 is a divalent metal atom or a metal oxide atom is preferable.
- Specific examples of the compound (1) include compounds represented by the formulas (2-1) to (2-38).
- the compound (1) is a compound which normally absorbs light having an orange color near 590 nm and has an absorption maximum wavelength (? Max) of 570 nm or more and 620 nm or less, more preferably 575 nm or more and 615 nm or less.
- the colorant (A) includes a red coloring matter.
- examples of the red dye include red pigment and red dye.
- red pigment known pigments can be used, and among the pigments classified as pigments in the color index (The Society of Dyers and Colourists), red pigments can be cited. Two or more species may be used in combination. However, the compound (1) is excluded.
- red pigments anthraquinone pigments, azo pigments, quinacridone pigments, perylene pigments and diketopyrrolopyrrole pigments are preferable, and C.I. Pigment Red 177, 179, 202, 208, 242, 254, 269, brominated diketopyrrolopyrrole pigments are preferred, and C.I. Pigment Red 177, 254, and a diketopyrrolopyrrole bromide pigment are more preferable.
- red dye examples include dyes such as oil-soluble dyes, acid dyes, basic dyes, direct dyes, mordant dyes, amine salts of acid dyes and sulfonamide derivatives of acid dyes. and Colourists), compounds classified as other than pigments, or known dyes described in dyeing notes (coloring yarn).
- dyes such as oil-soluble dyes, acid dyes, basic dyes, direct dyes, mordant dyes, amine salts of acid dyes and sulfonamide derivatives of acid dyes. and Colourists
- compounds classified as other than pigments or known dyes described in dyeing notes (coloring yarn).
- azo dyes, anthraquinone dyes, xanthine dyes, cyanine dyes, naphthoquinone dyes, quinone imine dyes, methine dyes, azomethine dyes and acridine dyes can be cited.
- organic solvent-soluble dyes are preferred. These dyes may be used in combination
- the red curable resin composition of the present invention may contain, as the colorant (A), a colorant other than the compound (1) (hereinafter sometimes referred to as a colorant (A1)) together with the compound (1) .
- a colorant (A1) a colorant other than the compound (1)
- the colorant (A1) may be a dye or a pigment.
- the dyes include known dyes (except for red dyes) described in Color Index (published by The Society of Dyers and Colourists) and dyeing notes (Colored Yarn).
- organic solvent-soluble dyes are preferred. These dyes may be used in combination of two or more.
- dyes having the following color index (CI) numbers can be mentioned.
- a known pigment can be used, and for example, a pigment classified as pigment in the color index (The Society of Dyers and Colourists) can be mentioned. Two or more species may be used in combination.
- Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73;
- C.I. Violet pigments such as Pigment Violet 1, 19, 23, 29, 32, 36, 38;
- the colorant (A1) is preferably one or both of a yellow coloring matter and an orange coloring matter, more preferably a yellow coloring matter. That is, it is more preferable that the colorant (A) further contains a yellow colorant in addition to the tetraazaporphyrin compound and the red colorant.
- yellow pigments and / or orange pigments are preferable, and yellow pigments are more preferable.
- the red pigment and the pigment may be subjected to a surface treatment using a rosin treatment, a coloring agent derivative into which an acidic group or a basic group has been introduced, A graft treatment to the surface of the substrate, an atomization treatment using a sulfuric acid atomization method, a cleaning treatment with an organic solvent or water to remove impurities, a removal treatment with an ion exchange method of ionic impurities, or the like.
- the particle diameters of the pigment and the like are preferably substantially uniform.
- the pigment is dispersed uniformly in the dispersion by carrying out dispersion treatment with a dispersant.
- a surfactant and the like can be mentioned, and any surfactant of cationic, anionic, nonionic or amphoteric type may be used. Specific examples thereof include surfactants such as polyester-based, polyamine-based, and acrylic-based surfactants.
- a resin (B) described below may be used. These dispersants may be used alone or in combination of two or more.
- dispersing agent examples include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), fluorene (manufactured by Kyowa Chemical Industry Co., Ltd.), Solsperse (manufactured by Zeneca), EFKA (registered trademark) (Manufactured by BASF), Ajisper (registered trademark) (manufactured by Ajinomoto Fine Techno Co., Ltd.) and Disperbyk (registered trademark) (manufactured by BICKEMISA), and BYK (registered trademark) (manufactured by BICKEMISA).
- the amount of the dispersing agent to be used is preferably 100 parts by mass or less, more preferably 5 parts by mass or more and 50 parts by mass or less based on 100 parts by mass of the pigment.
- the amount of the dispersing agent used is within the above range, there is a tendency that a more uniformly dispersed pigment dispersion is obtained.
- the content of the compound (1) is preferably 0.2 mass% or more and 20 mass% or less, more preferably 0.5 mass% or more and 15 mass% or less, and further preferably 1 mass% or more and 12 mass% or less, with respect to the entire solid content .
- the content of the red pigment is preferably 45 to 80 mass%, more preferably 47 to 75 mass%, and even more preferably 50 to 70 mass%, in 100 mass% of the colorant.
- the content of the red pigment is preferably 1% by mass or more and 50% by mass or less, more preferably 5% by mass or more and 45% by mass or less, and still more preferably 10% by mass or more and 40% by mass or less with respect to the entire solid content.
- the content of the compound (1) is preferably 0.1 part by mass or more and 200 parts by mass or less, more preferably 1 part by mass or more and 100 parts by mass or less, more preferably 1 part by mass or more and 70 parts by mass or less, Is more preferable.
- the content of the colorant (A1) (preferably yellow pigment) is usually 0 mass% or more and 50 mass% or less, preferably 0 mass% or more and 40 mass% or less, and more preferably 0 mass % Or more and 30 mass% or less.
- the content of the red pigment and the yellow pigment in the colorant is preferably 65 mass% or more and 97 mass% or less, more preferably 70 mass% or more and 95 mass% or less, more preferably 75 mass% or more and 93 mass% By mass or less.
- the content of the colorant (A) is preferably 5 mass% or more and 60 mass% or less, more preferably 8 mass% or more and 55 mass% or less, and further preferably 10 mass% or more and 50 mass% or less, based on the entire solid content .
- the term " total solid content " in this specification refers to the amount excluding the solvent content from the total amount of the red curable resin composition.
- the total solid content and the content of each component in the solid content can be measured by known analytical means such as liquid chromatography or gas chromatography.
- the resin (B) is not particularly limited, but is preferably an alkali-soluble resin, and at least one kind (a) (hereinafter referred to as "(a)") selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride ) Is more preferable.
- the resin (B) may further contain a structural unit derived from a monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter also referred to as "(b)") (Hereinafter sometimes referred to as " (c) ") which is copolymerizable with the monomer (c) (provided that (a) and (b) are different), and a structural unit derived from an ethylenically unsaturated bond Having at least one kind of structural unit selected from the group consisting of structural units having the above-mentioned structural units.
- a structural unit derived from a monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond hereinafter also referred to as "(b)"
- " ethylenically unsaturated bond
- (meth) acrylic acid means at least one kind selected from the group consisting of acrylic acid and methacrylic acid.
- the expressions such as “(meth) acryloyl” and “(meth) acrylate” have the same meaning.
- (b) is a monomer having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of oxirane rings, oxetane rings and tetrahydrofuran rings) and a monomer having a (meth) acryloyloxy group .
- (meth) acrylate vinylbenzyl glycidyl ether, 3,4-epoxy tricyclo [5.2.1.0 2,6 ] decyl (meth) acrylate, 3-ethyl (Meth) acryloyloxymethylthioxetane, tetrahydrofurfuryl (meth) acrylate and the like, and preferred examples thereof include glycidyl (meth) acrylate, 3,4-epoxy tricyclo [ 5.2.1.0 2,6 ] decyl (meth) acrylate, 3-ethyl-3- (meth) acryloyloxymethyloxetane.
- the resin having a structural unit having an ethylenically unsaturated bond in the side chain may be obtained by adding (b) to the copolymer of (a) and (c), or by adding (a) to the copolymer of (b) .
- the resin may be a resin obtained by adding (a) to a copolymer of (b) and (c) and further reacting with a carbonic anhydride.
- the weight average molecular weight of the resin (B) in terms of polystyrene is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and still more preferably 5,000 to 30,000.
- the molecular weight distribution (weight average molecular weight (Mw) / number average molecular weight (Mn)) of the resin (B) is preferably 1.1 to 6, and more preferably 1.2 to 4.
- the acid value of the resin (B) is preferably 50 to 170 mg-KOH / g, more preferably 60 to 150 mg-KOH / g, and still more preferably 70 to 135 mg-KOH / g in terms of solid content.
- the acid value is a value measured as an amount (mg) of potassium hydroxide necessary for neutralizing 1 g of the resin (B), and can be obtained by titration using, for example, an aqueous potassium hydroxide solution.
- the content of the resin (B) is preferably from 10 to 70 mass%, more preferably from 15 to 65 mass%, and still more preferably from 20 to 60 mass%, based on the whole solid content.
- the polymerizable compound (C) is a compound which can be polymerized by an active radical and / or an acid generated from the polymerization initiator (D), for example, a compound having a polymerizable ethylenic unsaturated bond, Is a (meth) acrylic acid ester compound.
- the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenic unsaturated bonds.
- examples of such polymerizable compounds include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) , Dipentaerythritol hexa (meth) acrylate, and the like.
- the weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, and more preferably 250 or more and 1,500 or less.
- the content of the polymerizable compound (C) is preferably 3 to 60 mass%, more preferably 5 to 50 mass%, and still more preferably 11 to 40 mass%, based on the entire solid content.
- the polymerization initiator (D) is not particularly limited as far as it is a compound capable of generating an active radical, an acid or the like by the action of light or heat and capable of initiating polymerization, and a known polymerization initiator can be used.
- Examples of the polymerization initiator that generates an active radical include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-benzoyloxy- 2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropan- 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutan-1-one, 1-hydroxycyclohexyl Phenyl ketone 2,4-bis (trichloromethyl) -6-piperonyl-1,3,5-triazine, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,
- the polymerization initiator is preferably a polymerization initiator comprising at least one member selected from the group consisting of a triazine compound, an acylphosphine oxide compound, an alkylphenone compound, an O-acyloxime compound and a nonimidazole compound, and O- A polymerization initiator comprising a compound is more preferable.
- the content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, and more preferably 1 to 20 parts by mass, based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C).
- the content of the polymerization initiator (D) is within the above range, the sensitivity of the color filter tends to be shortened and the exposure time is shortened.
- the content of the O-acyloxime compound is preferably 50% by mass or more, more preferably 80% by mass or more, further preferably 90% by mass or more, and particularly preferably 90% by mass or more based on the total amount of the polymerization initiator (D) By mass is 95% by mass or more.
- the content of the O-acyloxime compound is within the above range, there is a tendency that a color filter having high sensitivity can be produced even when the sensitivity, developability and colorant content in forming a color pattern are high.
- the red curable resin composition of the present invention may contain a polymerization initiator.
- the polymerization initiator (D1) is a compound or a sensitizer used for promoting polymerization of a polymerizable compound initiated by polymerization initiator. When the polymerization initiator (D1) is included, it is usually used in combination with the polymerization initiator (D).
- Examples of the polymerization initiator (D1) include 4,4'-bis (dimethylamino) benzophenone (commonly referred to as Mihiraazuketone), 4,4'-bis (diethylamino) benzophenone, 9,10-dimethoxyanthracene, 2,4-diethyl thioxanthone N-phenylglycine, and the like.
- polymerization initiator (D1) When these polymerization initiator (D1) is used, its content is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, per 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C) Mass part. When the amount of the polymerization initiator (D1) is within this range, it is possible to form a colored pattern with higher sensitivity, and the productivity of the color filter tends to be improved.
- the red curable resin composition of the present invention preferably contains a solvent.
- the solvent (E) is not particularly limited, and a solvent commonly used in the art can be used.
- a solvent commonly used in the art can be used.
- an ester solvent a solvent containing -COO- in the molecule and containing no -O-
- an ether solvent a solvent containing -O- and no -COO- in the molecule
- an ether ester Solvent containing -COO- and -O- in the molecule
- ketone solvent solvent containing -CO- in the molecule and not including -COO-
- alcohol solvent containing OH in the molecule, O-, -CO- and -COO-
- aromatic hydrocarbon solvents amide solvents, dimethylsulfoxide, and the like.
- Ester solvents such as ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, n-butyl acetate, ethyl butyrate, butyl butyrate, ethyl pyruvate, methyl acetoacetate, cyclohexanol acetone and? -Butyrolactone;
- Ether solvents such as ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, 3-methoxy-1-butanol, diethylene glycol dimethyl ether and diethylene glycol methyl ethyl ether;
- Ether ester solvents such as methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, 3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate and diethylene glycol monoethyl ether acetate;
- Ketone solvents such as 4-hydroxy-4-methyl-2-pentanone, heptanone, 4-methyl-2-pentanone and cyclohexanone;
- Alcohol solvents such as butanol, cyclohexanol and propylene glycol
- Aromatic hydrocarbon solvents such as toluene and xylene
- Amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidone.
- propylene glycol monomethyl ether acetate propylene glycol monomethyl ether
- ethyl lactate propylene glycol monomethyl ether
- ethyl 3-ethoxypropionate are more preferable.
- the content of the solvent (E) is preferably 70 to 95 mass%, more preferably 75 to 92 mass%, based on the total amount of the red curable resin composition of the present invention.
- the total amount of solids in the red curable resin composition is preferably 5 to 30% by mass, and more preferably 8 to 25% by mass.
- the red curable resin composition of the present invention may contain additives known in the art such as leveling agents, fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, and chain transfer agents, if necessary.
- the red curable resin composition of the present invention can be prepared by mixing a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), a solvent (E) .
- Examples of the method for producing a colored pattern with the red-curable resin composition of the present invention include a photolithographic method, an ink-jet method, and a printing method. Among them, the photolithography method is preferable. In the photolithography method, a colored coating film which is a cured product of the colored resin composition layer can be formed by not using a photomask during exposure and / or not developing it. The coloring pattern or colored coating film thus formed is the color filter of the present invention.
- a color filter of a high color (high chroma) and a thin film can be produced.
- a color filter is useful as a color filter used in a display device (e.g., a liquid crystal display device, an organic EL device, an electronic paper, etc.) and a solid-state image pickup device.
- red curable resin composition of the present invention will be described in more detail by examples.
- "% " and " part " are by mass% and mass part, unless otherwise specified.
- the compound represented by the formula (a-1) represents a compound represented by the formula (a-1-1) to the formula (a-1-4), and the product obtained by the above synthesis method is a mixture of these isomers.
- a compound represented by the formula (S-1) was obtained by the synthesis method described in JP-A-2016-27075.
- a flask equipped with a reflux condenser, a dropping funnel and a stirrer was charged with an appropriate amount of nitrogen and replaced with a nitrogen atmosphere. Then, 141 parts of ethyl lactate and 178 parts of propyleneglycol monomethylether acetate were added and heated to 85 ⁇ with stirring.
- the weight average molecular weight (Mw) and the number average molecular weight (Mn) of the resin in terms of polystyrene were measured by the GPC method under the following conditions.
- HLC-8120 GPC manufactured by Tosoh Corporation
- the ratio (Mw / Mn) of the weight average molecular weight and the number average molecular weight in terms of polystyrene obtained as described above was dispersed.
- Tetraazaporphyrin 17 parts of a compound represented by the formula (a-1)
- Red pigment Dispersion 1 435 parts
- Resin (B) Resin (B-1) (in terms of solid content) 29 parts
- Polymerizable compound (C) 35 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Yakuzaku Co., Ltd.)
- Leveling agent Polyether-modified silicone oil (in terms of solid content) (Toray Silicone SH8400, manufactured by Toray Dow Corning Co., Ltd.) 0.10 part
- a red curable resin composition was obtained in the same manner as in Example 1 except that the compound represented by the formula (a-2) was used instead of the compound represented by the formula (a-1).
- a red curable resin composition was obtained in the same manner as in Example 1 except that the compound represented by the formula (a-3) was used in place of the compound represented by the formula (a-1).
- a red curable resin composition was obtained in the same manner as in Example 1 except that the compound represented by the formula (a-4) was used in place of the compound represented by the formula (a-1).
- a red curable resin composition was obtained in the same manner as in Example 1 except that the compound represented by the formula (a-5) was used in place of the compound represented by the formula (a-1).
- Tetraaza porphyrin 11 parts of the compound represented by the formula (a-1)
- Red dye 16 parts of a compound represented by the formula (S-1)
- Resin (B) Resin (B-1) (in terms of solid content) 35 parts
- Polymerizable compound (C) 35 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Yakuzaku Co., Ltd.)
- Leveling agent Polyether-modified silicone oil (in terms of solid content) (Toray Silicone SH8400, manufactured by Toray Dow Corning Co., Ltd.) 0.10 part
- Tetraazaporphyrin 17 parts of a compound represented by the formula (a-1)
- Red pigment Dispersion 2 80 parts
- Resin (B) Resin (B-1) (in terms of solid content) 30 parts
- Polymerizable compound (C) 35 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Yakuzaku Co., Ltd.)
- Leveling agent Polyether-modified silicone oil (in terms of solid content) (Toray Silicone SH8400, manufactured by Toray Dow Corning Co., Ltd.) 0.10 part
- Tetraaza porphyrin 19 parts of a compound represented by the formula (a-1)
- Resin (B) Resin (B-1) (in terms of solid content) 9 parts
- Polymerizable compound (C) 35 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Yakuzaku Co., Ltd.)
- Leveling agent Polyether-modified silicone oil (in terms of solid content) (Toray Silicone SH8400, manufactured by Toray Dow Corning Co., Ltd.) 0.10 part
- Resin (B) Resin (B-1) (in terms of solid content) 20 parts
- Polymerizable compound (C) 35 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Yakuzaku Co., Ltd.)
- Leveling agent Polyether-modified silicone oil (in terms of solid content) (Toray Silicone SH8400, manufactured by Toray Dow Corning Co., Ltd.) 0.10 part
- the red curable resin composition was coated on a glass substrate (Eagle 2000; Corning) having a 5 cm edge by spin coating, and then pre-baked at 100 ⁇ ⁇ for 3 minutes to form a colored resin composition layer. After cooling, the substrate was irradiated with light at an exposure dose of 60 mJ / cm 2 (365 nm standard) in an air atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.). Thereafter, post-baking was performed in an oven at 230 DEG C for 20 minutes to obtain a color filter.
- the film thickness was measured using a film thickness measuring device (DEKTAK3; manufactured by Japan Vacuum Technology Co., Ltd.)). The results are shown in Table 1.
- the color filter formed of the red curable resin composition of the present invention can be said to be a color filter having a film thickness of 3 ⁇ or less, a high color (high chroma) and a thin film.
- the color filter formed of the red curable resin composition of the comparative example although it is possible to reproduce a red color having a high color (high chroma), thinning can not be achieved.
- the red curable resin composition of the present invention it is possible to form a color filter having a high color (high chroma) and a thin film.
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- Nonlinear Science (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Architecture (AREA)
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- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Materials For Photolithography (AREA)
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Abstract
Selon la présente invention, l'amincissement de films dans une région très colorée (à saturation élevée) peut parfois être réalisé de manière suffisamment satisfaisante dans un filtre coloré et dans un dispositif d'affichage tous deux constitués d'une composition de résine durcissable rouge traditionnellement connue. La présente invention porte sur une composition de résine durcissable rouge contenant un colorant, une résine, un composé polymérisable et un amorceur de polymérisation, le colorant contenant un composé de tétraazaporphyrine et une couleur rouge, sur un filtre coloré, et sur un dispositif d'affichage.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201880080662.0A CN111512232A (zh) | 2017-12-27 | 2018-12-12 | 红色固化性树脂组合物、滤色器及显示装置 |
| KR1020207010450A KR102508777B1 (ko) | 2017-12-27 | 2018-12-12 | 적색 경화성 수지 조성물, 컬러 필터 및 표시 장치 |
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| Application Number | Priority Date | Filing Date | Title |
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| JP2017-250683 | 2017-12-27 | ||
| JP2017250683A JP7077012B2 (ja) | 2017-12-27 | 2017-12-27 | 赤色硬化性樹脂組成物、カラーフィルタ、及び表示装置 |
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|---|---|
| WO2019132328A1 true WO2019132328A1 (fr) | 2019-07-04 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/KR2018/015769 Ceased WO2019132328A1 (fr) | 2017-12-27 | 2018-12-12 | Composition de résine durcissable rouge, filtre coloré, et dispositif d'affichage |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP7077012B2 (fr) |
| KR (1) | KR102508777B1 (fr) |
| CN (1) | CN111512232A (fr) |
| TW (1) | TWI734946B (fr) |
| WO (1) | WO2019132328A1 (fr) |
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| JP7626600B2 (ja) | 2019-12-09 | 2025-02-04 | 東友ファインケム株式会社 | 着色硬化性樹脂組成物、カラーフィルタ、及び表示装置 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003506526A (ja) * | 1999-07-30 | 2003-02-18 | ディーエスエム エヌ.ブイ. | 硬化中の同時的色形成を伴う照射硬化性組成物 |
| KR20130133675A (ko) * | 2012-05-29 | 2013-12-09 | 스미또모 가가꾸 가부시키가이샤 | 착색 경화성 수지 조성물 |
| KR20160056294A (ko) * | 2014-11-11 | 2016-05-19 | 스미또모 가가꾸 가부시키가이샤 | 착색 경화성 수지 조성물 |
| KR20170003378A (ko) * | 2015-06-30 | 2017-01-09 | 동우 화인켐 주식회사 | 착색 경화성 수지 조성물, 컬러 필터 및 액정표시장치 |
| KR20170110380A (ko) * | 2016-03-23 | 2017-10-11 | 동우 화인켐 주식회사 | 착색 경화성 수지 조성물 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2011178942A (ja) | 2010-03-03 | 2011-09-15 | Konica Minolta Business Technologies Inc | 着色剤、着色剤組成物、電子写真用トナー、カラーフィルター及びディスプレイ用前面フィルター |
| JP5775482B2 (ja) * | 2011-09-30 | 2015-09-09 | 富士フイルム株式会社 | 着色硬化性組成物、カラーフィルタ、カラーフィルタの製造方法、及び表示装置 |
| JP5770672B2 (ja) * | 2012-03-30 | 2015-08-26 | 富士フイルム株式会社 | 着色硬化性組成物、カラーフィルタ、カラーフィルタの製造方法、および表示装置 |
| CN105319848B (zh) * | 2014-07-29 | 2021-03-26 | 住友化学株式会社 | 着色固化性树脂组合物 |
| JP6852971B2 (ja) * | 2016-02-24 | 2021-03-31 | 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. | 着色硬化性樹脂組成物、カラーフィルタ及び液晶表示装置 |
-
2017
- 2017-12-27 JP JP2017250683A patent/JP7077012B2/ja active Active
-
2018
- 2018-12-12 CN CN201880080662.0A patent/CN111512232A/zh active Pending
- 2018-12-12 KR KR1020207010450A patent/KR102508777B1/ko active Active
- 2018-12-12 WO PCT/KR2018/015769 patent/WO2019132328A1/fr not_active Ceased
- 2018-12-22 TW TW107146637A patent/TWI734946B/zh active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003506526A (ja) * | 1999-07-30 | 2003-02-18 | ディーエスエム エヌ.ブイ. | 硬化中の同時的色形成を伴う照射硬化性組成物 |
| KR20130133675A (ko) * | 2012-05-29 | 2013-12-09 | 스미또모 가가꾸 가부시키가이샤 | 착색 경화성 수지 조성물 |
| KR20160056294A (ko) * | 2014-11-11 | 2016-05-19 | 스미또모 가가꾸 가부시키가이샤 | 착색 경화성 수지 조성물 |
| KR20170003378A (ko) * | 2015-06-30 | 2017-01-09 | 동우 화인켐 주식회사 | 착색 경화성 수지 조성물, 컬러 필터 및 액정표시장치 |
| KR20170110380A (ko) * | 2016-03-23 | 2017-10-11 | 동우 화인켐 주식회사 | 착색 경화성 수지 조성물 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2019116544A (ja) | 2019-07-18 |
| KR20200093524A (ko) | 2020-08-05 |
| JP7077012B2 (ja) | 2022-05-30 |
| TW201927917A (zh) | 2019-07-16 |
| KR102508777B1 (ko) | 2023-03-10 |
| TWI734946B (zh) | 2021-08-01 |
| CN111512232A (zh) | 2020-08-07 |
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