WO2017164127A1 - 着色樹脂組成物、カラーフィルタ基板、および液晶表示装置 - Google Patents
着色樹脂組成物、カラーフィルタ基板、および液晶表示装置 Download PDFInfo
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- WO2017164127A1 WO2017164127A1 PCT/JP2017/010964 JP2017010964W WO2017164127A1 WO 2017164127 A1 WO2017164127 A1 WO 2017164127A1 JP 2017010964 W JP2017010964 W JP 2017010964W WO 2017164127 A1 WO2017164127 A1 WO 2017164127A1
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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
- G03F7/031—Organic compounds not covered by group G03F7/029
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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
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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
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
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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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/24—Electrically-conducting paints
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
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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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
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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
- 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
- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
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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
- G02F2202/00—Materials and properties
- G02F2202/02—Materials and properties organic material
- G02F2202/022—Materials and properties organic material polymeric
- G02F2202/023—Materials and properties organic material polymeric curable
- G02F2202/025—Materials and properties organic material polymeric curable thermocurable
Definitions
- the present invention relates to a colored resin composition, a color filter substrate, and a liquid crystal display device.
- Liquid crystal display devices are used in various applications such as televisions, notebook computers, personal digital assistants, smartphones, digital cameras, etc., taking advantage of their characteristics such as light weight, thinness, and low power consumption.
- Liquid crystal display devices are required to display optimal colors of 3 to 6 primary colors depending on the application. Searching for an optimal color material as a colorant composition used for a pixel of a color filter substrate responsible for the color performance of a liquid crystal display device.
- green pigments having a phthalocyanine skeleton include C.I. I. Pigment green 36 (brominated copper phthalocyanine), C.I. I. A polyhalogenated copper phthalocyanine such as CI Pigment Green 7 (odor chlorinated copper phthalocyanine); I. Pigment green 58 (brominated zinc phthalocyanine), C.I. I. There are polyhalogenated zinc phthalocyanines such as CI Pigment Green 59 (odor chlorinated zinc phthalocyanine).
- a yellow pigment such as CI Pigment Yellow 139 is used in combination.
- it is also common to use a plurality of yellow pigments in combination as yellow pigments (Patent Documents 2 and 3).
- the combination of Pigment Yellow 138 is preferred because it has a high initial transmittance (Patent Documents 2 and 3).
- Non-Patent Document 1 discloses that this phenomenon can be alleviated by modifying the phthalocyanine skeleton with a substituent.
- a technique of adding a light stabilizer such as hindered amine in order to improve the light resistance of the color filter is known (Patent Document 4).
- JP, 2014-41341 A Japanese Patent Laid-Open No. 2015-169880 JP 2012-141368 A JP 2011-102833
- an object of this invention is to provide the colored resin composition with a high transmittance
- the present invention contains polyhalogenated zinc phthalocyanine, a yellow pigment, a binder resin and a compound of the following general formula (1).
- R 1 is H, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, carbon Selected from an arylalkyl group having 7 to 30 atoms, an arylalkyloxy group having 7 to 30 carbon atoms, a heterocyclic group having 2 to 20 carbon atoms, CN, a halogen atom and a group represented by the general formula (2) Represents a group.
- R 4 represents a group selected from an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and an arylalkyl group having 7 to 30 carbon atoms, and R 4 represents an adjacent benzene ring And may form a ring.
- R 5 and R 6 are each independently an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an aryloxy group having 6 to 30 carbon atoms.
- a and b are each independently 0 to 3;
- R 2 is selected from an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, a heterocyclic group having 2 to 20 carbon atoms, and CN.
- R 21 , R 22 and R 23 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or the number of carbon atoms It represents a 7-30 arylalkyl group or a heterocyclic group having 2-20 carbon atoms.
- R 3 is an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, or 7 to 7 carbon atoms.
- the alkyl group may have a straight chain or a branched side chain, and may be a cyclic alkyl, and an unsaturated bond, ether bond, thioether bond, ester bond, thioester bond, amide bond and It may contain 1 to 5 bonds selected from urethane bonds.
- the present invention is a color filter substrate having pixels formed using the above colored resin composition.
- the present invention also relates to a liquid crystal display device in which a color filter substrate and a counter substrate are bonded, a liquid crystal compound is filled between the two and a backlight is attached, and the color filter substrate is polyhalogenated. It has a pixel containing zinc phthalocyanine, a yellow pigment, a binder resin and a compound represented by the above general formula (1).
- the liquid crystal display device is at least one selected from the group consisting of CI Pigment Yellow 185, and the backlight has a luminance of 8000 to 100,000 cd / m 2 .
- the inventors have conducted intensive studies on the above-described transmittance reduction phenomenon.
- This phenomenon occurs in phthalocyanine-based green pigments, and is particularly remarkable in polyhalogenated zinc phthalocyanine (for example, CI Pigment Green 58). I found out.
- polyhalogenated zinc phthalocyanine and a specific yellow pigment for example, CI Pigment Yellow 138
- this transmittance reduction phenomenon occurs when light is irradiated in an oxygen-blocked state, and after the light irradiation is completed, the transmittance is recovered when it is opened to the atmosphere and exposed to an atmosphere containing oxygen. I found out.
- this transmittance reduction phenomenon is presumed to be a phenomenon caused by excitation of the phthalocyanine pigment, and as a result of intensive studies on a deactivator that eliminates the excited state, it is represented by the following general formula (1). It has been found that a compound having a nitrocarbazole skeleton has a particularly high effect as a deactivator.
- the excited state of the polyhalogenated zinc phthalocyanine is deactivated, and the decrease in transmittance due to light irradiation at the time of blocking oxygen is prevented. Can do.
- R 1 is H, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, carbon Arylalkyl group having 7 to 30 atoms, arylalkyl group having 7 to 30 carbon atoms, arylalkyloxy group having 7 to 30 carbon atoms, heterocyclic group having 2 to 20 carbon atoms, CN, halogen atom and the like
- the group selected from the group represented by Formula (2) is represented.
- R 4 represents a group selected from an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and an arylalkyl group having 7 to 30 carbon atoms, and R 4 represents an adjacent benzene ring And may form a ring together.
- R 5 and R 6 are each independently an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an aryloxy group having 6 to 30 carbon atoms.
- R 2 is selected from an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, a heterocyclic group having 2 to 20 carbon atoms, and CN.
- R 21 , R 22 and R 23 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or the number of carbon atoms It represents a 7-30 arylalkyl group or a heterocyclic group having 2-20 carbon atoms.
- R 3 is an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, or 7 to 7 carbon atoms.
- the alkyl group may have a straight chain or a branched side chain, and may be a cyclic alkyl, and an unsaturated bond, ether bond, thioether bond, ester bond, thioester bond, amide bond and It may contain 1 to 5 bonds selected from urethane bonds.
- the compound represented by the general formula (1) is a nitrocarbazole compound in which a nitro group is substituted on one benzene ring of the carbazole skeleton.
- the other benzene ring of the carbazole skeleton may be unsubstituted or may be substituted with the substituent exemplified above. Examples of such compounds include the following 9-ethyl-3-nitrocarbazole.
- R 1 when R 1 is a group represented by the general formula (2), it not only functions as a deactivator but also functions as a photopolymerization initiator.
- this compound itself is well-known, and is described in patent 4223071 publication, The manufacturing method is also described in this gazette. Commercial products may be used.
- this compound When this compound is used as a photopolymerization initiator, sufficient photocuring is possible not only with i-line (365 nm) but also with long-wavelength exposure such as h-line (405 nm). It is possible to correspond to an amount of exposure method.
- the content of the compound represented by the general formula (1) is preferably 0.1 to 50% by mass, more preferably 2 to 20% by mass in the solid component.
- the content is 0.1% by mass or less, the effect of improving the transmittance retention rate is lowered.
- membrane may become weak.
- the “solid component” refers to the sum of components other than the solvent among the components contained in the colored resin composition.
- the colored resin composition of the present invention contains a colorant, a binder resin, and a compound of the above general formula (1).
- C. I. Pigment yellow 138 and C.I. I pigment yellow 185 has a high initial transmittance.
- C.I. I. Pigment Green 58 and C.I. I. In the present invention, there was a problem that the transmittance was significantly lowered when Pigment Yellow 138 was used in combination.
- the transmittance was increased. The problem of degradation can be solved.
- the preferable range of the content of the colorant is 1 to 65% by mass in the solid component, more preferably 10 to 55% by mass, and further preferably 10 to 50% by mass. When it is lower than 1% by mass, the coloring performance is lowered. Moreover, when it exceeds 65 mass%, a film
- Polyhalogenated zinc phthalocyanine includes C.I. I. Pigment green 58 and C.I. I. One or more selected from CI Pigment Green 59 are preferred.
- the polyhalogenated zinc phthalocyanine when the total content of the colorant in the colored resin composition is 100% by mass is 10 to 99 in the total colorant. It is preferable to be contained by mass%.
- the ratio of the polyhalogenated zinc phthalocyanine is more preferably 15% by mass or more, and further preferably 72% by mass or more. The ratio is more preferably 95% by mass or less. The higher the ratio of the polyhalogenated phthalocyanine, the lower the colorant concentration, and the higher the resin component, the higher the reliability of the color filter obtained.
- the yellow pigment is preferably contained in an amount of 1 to 90% by mass, more preferably 5 to 85% by mass, based on the whole colorant.
- C.I. I. Pigment Yellow 150 is also preferable.
- pigments selected from CI Pigment Yellow 185 C.I. I.
- Pigment Yellow 150 By further including Pigment Yellow 150, it is possible to further improve the transmittance retention rate in the weather resistance test under oxygen interruption without significantly reducing the initial transmittance.
- the total content of CI Pigment Yellow 185 is in the range of 20 to 85% by mass, more preferably in the range of 20 to 80% by mass, which is particularly excellent in terms of both initial transmittance and transmittance retention.
- the ratio of CI Pigment Yellow 150 is C.I. I.
- the pigment yellow 150 content is preferably in the range of 20 to 80% by mass.
- C.I. I. When CI Pigment Yellow 138 is used, polyhalogenated zinc phthalocyanine, C.I. I. Pigment Yellow 138 and binder resin, reactive monomer, and dispersant as a total of 100% by mass, polyhalogenated zinc phthalocyanine and C.I. I. A total content of CI Pigment Yellow 138 of 43 to 55% by mass is preferable because the luminance is easily increased.
- pigments may be contained as long as the properties are not impaired.
- C.I. I. Pigment Green 1, 2, 4, 7, 8, 10, 13, 14, 15, 17, 18, 19, 26, 36, 45, 48, 50, 51, 54, 55 C.I. I. Pigment Yellow 1, 1: 1, 2, 3, 4, 5, 6, 9, 10, 12, 13, 14, 16, 17, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 41, 42, 43, 48, 53, 55, 61, 62, 62: 1, 63, 65, 73, 74, 75, 81, 83, 87, 93, 94, 95, 97, 100, 101, 104, 105, 108, 109, 110, 111, 116, 117, 119, 120, 126, 127, 127: 1, 128, 129, 133, 134, 136, 139, 142, 147, 148, 151, 153, 154, 155, 157, 158, 159, 160, 161, 162,
- the binder resin is not particularly limited, but acrylic resin, epoxy resin, polyimide resin, urethane resin, urea resin, polyvinyl alcohol resin, melamine resin, polyamide resin, polyamideimide resin, polyester resin, polyolefin resin, and the like are preferable. .
- An acrylic resin is particularly preferably used from the viewpoint of stability.
- the acrylic resin is not particularly limited, but a copolymer of an unsaturated carboxylic acid and an ethylenically unsaturated compound can be preferably used.
- unsaturated carboxylic acid include acrylic acid, methacrylic acid, itaconic acid, crotonic acid, maleic acid, fumaric acid, vinyl acetic acid, and acid anhydrides.
- copolymerizable ethylenically unsaturated compounds examples include methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, n-propyl acrylate, isopropyl acrylate, n-propyl methacrylate, and methacrylic acid.
- an acrylic resin having an ethylenically unsaturated group added to the side chain when used as a photosensitive resin composition, the sensitivity at the time of processing is improved, so that it can be preferably used.
- the ethylenically unsaturated group include a vinyl group, an allyl group, an acrylic group, and a methacryl group.
- a method of adding such a side chain to an acrylic (co) polymer when the acrylic resin has a carboxyl group or a hydroxyl group, an ethylenically unsaturated compound having an epoxy group, acrylic acid chloride, A method of addition reaction of methacrylic acid chloride or the like is common.
- a compound having an ethylenically unsaturated group can be added using isocyanate.
- the acrylic resin having an unsaturated group in the side chain produced by such a method can be further purified by an ion exchange method or reprecipitation.
- the reprecipitation method include a method of precipitating the binder resin solution by mixing it with water or various organic solvents to obtain a powder.
- acrylic resin having an ethylenically unsaturated group in the side chain for example, a commercially available acrylic resin, Cyclomer (registered trademark) P (Daicel Chemical Industries, Ltd.) or an alkali-soluble cardo resin can be used.
- the mass average molecular weight Mw of the binder resin is preferably 3,000 to 200,000, more preferably 9000 to 100,000.
- the mass average molecular weight is less than 3,000, the strength of the obtained cured film is lowered.
- the mass average molecular weight Mw is a value measured by gel permeation chromatography and converted using a calibration curve of standard polystyrene.
- the preferable content of the binder resin is 1 to 99% by mass, more preferably 5 to 95% by mass in the solid component from the viewpoint of the balance between developability and color characteristics.
- the resin composition of the present invention may contain other additives.
- other additives include organic solvents, adhesion improvers, surfactants, and the like.
- organic solvent when an acrylic resin is used as the binder resin examples include diethylene glycol monobutyl ether acetate (boiling point 247 ° C.), benzyl acetate (boiling point 214 ° C.), ethyl benzoate (boiling point 213 ° C.), methyl benzoate (boiling point 200 ° C.).
- solvents examples include ethylene glycol monomethyl ether (boiling point 124 ° C.), ethylene glycol monoethyl ether (boiling point 135 ° C.), propylene glycol monoethyl ether (boiling point 133 ° C.), diethylene glycol monomethyl ether (boiling point 193 ° C.).
- the preferable range of the content of the organic solvent is 40 to 95% by mass, more preferably 50 to 90% by mass, based on the total amount of the colored resin composition.
- the adhesion improving agent can be preferably added for the purpose of improving the adhesion of the coating film to the substrate.
- the preferable range of the content of the adhesion improving agent is 10% by mass or less, more preferably 5% by mass or less in the solid component.
- Surfactant can be added for the purpose of improving the coating property of the resin composition and the uniformity of the surface of the layer.
- anionic surfactants such as ammonium lauryl sulfate and polyoxyethylene alkyl ether sulfate triethanolamine
- cationic surfactants such as stearylamine acetate and lauryltrimethylammonium chloride, lauryldimethylamine oxide, laurylcarboxymethylhydroxy
- amphoteric surfactants such as ethylimidazolium betaine
- nonionic surfactants such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, and sorbitan monostearate
- fluorine-based surfactants and silicon-based surfactants.
- the amount of the surfactant added is preferably 0.001 to 10% by mass with respect to the total amount. If the addition amount is less than this range, the effect of improving the coating property and the uniformity of the film surface is small, and if it is too large, the coating property is undesirably poor.
- the colored resin composition of the present invention can be used as a photosensitive resin composition or a non-photosensitive resin composition.
- a photosensitive resin composition it is preferable to further contain a reactive monomer and a photopolymerization initiator.
- the reactive monomer is not particularly limited, but polyfunctional (meth) acrylate is preferably used.
- polyfunctional (meth) acrylate is preferably used.
- R 1 is a group represented by the general formula (2) as a compound represented by the general formula (1), it only acts as a deactivator. And functions as a photopolymerization initiator.
- the photopolymerization initiator represented by the general formula (1) include Adeka Arkles (registered trademark) NCI-831 manufactured by ADEKA Corporation.
- photoinitiators other than the compound represented by General formula (1) can also be added.
- photopolymerization initiators examples include inorganic compounds such as benzophenone compounds, acetophenone compounds, imidazole compounds, benzothiazole compounds, benzoxazole compounds, oxime ester compounds, triazine compounds, phosphorus compounds, and titanates.
- inorganic compounds such as benzophenone compounds, acetophenone compounds, imidazole compounds, benzothiazole compounds, benzoxazole compounds, oxime ester compounds, triazine compounds, phosphorus compounds, and titanates.
- a photoinitiator is mentioned.
- benzophenone N, N′-tetraethyl-4,4′-diaminobenzophenone, 4-methoxy-4′-dimethylaminobenzophenone, 2,2-diethoxyacetophenone
- benzoin benzoin methyl ether
- Benzoin isobutyl ether benzyldimethyl ketal
- ⁇ -hydroxyisobutylphenone 1-hydroxycyclohexyl phenyl ketone
- 2-methyl-1- [4- (methylthio) phenyl] -2-morpholino-1-propane 2-methyl-1- [4- (methylthio) phenyl] -2-morpholino-1-propane
- Irgacure (registered trademark) 369 (2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone
- 379 (2- (dimethylamino) -2-[(4-methylphenyl) methyl]
- Chain transfer agents include thioglycolic acid, thiomalic acid, thiosalicylic acid, 2-mercaptopropionic acid, 3-mercaptopropionic acid, 3-mercaptobutyric acid, N- (2-mercaptopropionyl) glycine, 2-mercaptonicotinic acid, 3 -[N- (2-mercaptoethyl) carbamoyl] propionic acid, 3- [N- (2-mercaptoethyl) amino] propionic acid, N- (3-mercaptopropionyl) alanine, 2-mercaptoethanesulfonic acid, 3- Mercaptopropanesulfonic acid, 4-mercaptobutanesulfonic acid, dodecyl (4-methylthio) phenyl ether, 2-mercaptoethanol, 3-mercapto-1,2-propanediol, 1-
- the preferred range of the content of the chain transfer agent is 0.01 to 10% by mass, more preferably 0.1 to 3% by mass in the solid component. It is.
- sensitizer examples include thioxanthone sensitizers, aromatic or aliphatic tertiary amines, and the like. More specifically, for example, thioxanthone, 2-chlorothioxanthone, DETX-S (2,4-diethylthioxanthen-9-one) and the like can be mentioned.
- sensitizers can also be used in combination of two or more.
- the addition amount of the sensitizer is not particularly limited, but is preferably 2 to 30% by mass, more preferably 5 to 25% by mass with respect to the total solid components of the photosensitive composition.
- a polymerization inhibitor may be added.
- the polymerization inhibitor is not particularly limited.
- the preferred range of the content of the polymerization inhibitor is 0.0001 to 1% by mass in the solid component, more preferably 0.005 to 0.5% by mass. %.
- the colored resin composition is preferably produced by adding the other components after preparing a pigment dispersion by dispersing the pigment, binder resin and solvent with a disperser.
- a disperser include a sand mill, a ball mill, a bead mill, a three roll mill, and an attritor.
- a bead mill excellent in dispersion efficiency is preferred.
- the dispersed beads used in the bead mill include zirconia beads, alumina beads, and glass beads, but zirconia beads are preferable.
- a dispersant in order to improve the dispersion stability of the pigment.
- a pigment derivative a polymer dispersant, or the like can be used.
- the pigment derivative include a modified alkylamine of a pigment skeleton, a carboxylic acid derivative, and a sulfonic acid derivative.
- the pigment derivative is effective as a synergist to wet the pigment and stabilize the fine pigment.
- sulfonic acid derivatives of organic pigments are highly effective for stabilizing fine pigments and are preferably used.
- the polymer dispersant is not particularly limited as long as it is used for color filters, and polymers such as polyester, polyalkylamine, polyallylamine, polyimine, polyamide, polyurethane, polyacrylate, polyimide, polyamideimide, etc. These can be used alone or in combination.
- polymer dispersants those having an amine value and an acid value are preferable.
- those having an amine value in terms of solid content of 5 to 200 and an acid value of 1 to 100 are preferable.
- Use of these dispersants is preferably used because the storage stability of the pigment dispersion and thus the colored resin composition is improved.
- a colored resin composition can be obtained by mixing with a liquid.
- the color filter substrate of the present invention needs to form at least one color pixel using the colored resin composition of the present invention.
- the configuration of the other color filters is not particularly limited.
- a color filter in which red, green, and blue pixels are formed after a resin black matrix is formed on a transparent substrate is preferably used.
- the pigment used for the resin black matrix is not particularly limited as long as it plays a role as a light shielding agent.
- Pigment black 7, carbon black, graphite, iron oxide, manganese oxide, titanium black and the like, which are organic pigments, are used as a light shielding agent. It is also preferable to subject the pigment to a surface treatment. If necessary, a mixture of a plurality of light-shielding agents can be used, or pigments of other colors can be added.
- the pigment used for the red pixel is not particularly limited as long as it plays a role.
- red pigments include Pigment Red 9, 48, 97, 122, 123, 144, 149, 166, 168, 177, 179, 180, 192, 209, 215, 216, 217, 220, 223, 224, and 226. 227, 228, 240, 254, etc. are used.
- yellow pigments include Pigment Yellow 12, 13, 17, 20, 24, 83, 86, 93, 95, 109, 110, 117, 125, 129, 137, 138, 139, 147, 148, 150, 153. 154, 166, 168, 185, etc. are used.
- orange pigments include pigment oranges 13, 36, 38, 43, 51, 55, 59, 61, 64, 65, 71, and the like.
- the pigment used for the blue pixel is not particularly limited as long as it plays a role.
- examples of blue pigments include pigment blue 15, 15: 3, 15: 4, 15: 6, 22, 60, 64, and the like. Pigment Violet 19, 23, 29, 30, 32, 37, 40, 50, etc. are used.
- the colored resin composition of the present invention is preferably used.
- a colored resin composition is applied on a substrate.
- a coating method a method of applying a colored resin composition to a substrate using a spin coater, a bar coater, a blade coater, a roll coater, a die coater, an ink jet printing method, a screen printing method, etc., the substrate in the colored resin composition
- Various methods such as a dipping method and spraying a colored resin composition onto a substrate can be used.
- a transparent substrate such as soda glass, non-alkali glass, borosilicate glass, or quartz glass is preferably used.
- a coating film of the colored resin composition is formed by air drying, heat drying, vacuum drying or the like.
- a mask is set on the coating film of the colored resin composition, and exposure is selectively performed with ultraviolet rays using an ultrahigh pressure mercury lamp, a chemical lamp, a high pressure mercury lamp, or the like.
- the exposure machine can be used regardless of proximity, mirror projection, lens scanning and the like.
- the lens scanning method is preferable from the viewpoint of accuracy.
- alkaline developer examples include inorganic alkalis such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium silicate, sodium metasilicate, aqueous ammonia, ethylamine, n-propylamine and the like.
- Secondary amines such as tertiary amines, diethylamine and di-n-propylamine; tertiary amines such as triethylamine and methyldiethylamine; and organic alkalis such as tetramethylammonium hydroxide.
- the obtained coating film pattern is heat-treated to form a color filter substrate on which pixels are patterned.
- the heat treatment is usually continuous or stepwise for 0.5 to 5 hours at a temperature of 150 to 350 ° C., preferably 180 to 250 ° C. in the air, in a nitrogen atmosphere, or in a vacuum. To be done. By this heating step, curing of the resin component of the photosensitive colorant composition proceeds.
- the patterning process is sequentially performed for each pixel of the black matrix and 3 to 6 primary colors.
- An overcoat film may be formed thereon if necessary.
- the overcoat film include an epoxy film, an acrylic epoxy film, an acrylic film, a siloxane polymer film, a polyimide film, a silicon-containing polyimide film, and a polyimidesiloxane film.
- a transparent conductive film may be further formed on the overcoat film.
- the transparent conductive film examples include a metal oxide thin film such as ITO having a thickness of about 0.1 ⁇ m.
- Examples of the method for producing the ITO film include a sputtering method and a vacuum evaporation method.
- a fixed spacer may be formed on the color filter substrate.
- the fixed spacer refers to a spacer that is fixed at a specific location on the color filter substrate and contacts the counter substrate when a liquid crystal display device is manufactured. As a result, a certain gap is maintained between the color filter substrate and the counter substrate, and the liquid crystal compound is filled in the gap.
- a liquid crystal display device can be manufactured by laminating a color filter substrate and a counter substrate and filling a gap between them with a liquid crystal compound.
- a counter substrate for example, a counter substrate in which a liquid crystal alignment film subjected to a rubbing process for liquid crystal alignment is provided on a driving element substrate having a thin film diode (TFD) element, a scanning line, a signal line, and a transparent electrode Can be used.
- TFD thin film diode
- the color filter substrate was also rubbed for liquid crystal alignment.
- the counter substrate and the color filter substrate are opposed to each other and bonded together using a sealing material.
- the injection port is sealed, a backlight is attached, and an IC driver or the like is mounted to complete a liquid crystal display device.
- a white LED made of a blue LED and a YAG phosphor can be used.
- the color filter substrate has a pixel containing a polyhalogenated zinc phthalocyanine, a yellow pigment, a binder resin and a compound represented by the general formula (1).
- I. Pigment yellow 150, C.I. I. Pigment yellow 138 and C.I. I. At least one selected from the group consisting of CI Pigment Yellow 185.
- the luminance of the backlight is preferably 8000 to 100,000 cd / m 2 , more preferably 10,000 to 50,000 cd / m 2 , and further preferably 15,000 to 30,000 cd / m 2 .
- a higher backlight intensity is preferable because the visibility of the liquid crystal display device is improved.
- the transmittance reduction phenomenon which is a problem of the prior art, is proportional to the luminance. When the luminance of the backlight is 8000 cd / m 2 or more, the transmittance is significantly reduced.
- the colored resin composition of the present invention is used, so that this transmittance reduction phenomenon can be prevented, so that the visibility of the liquid crystal display device can be improved by setting the luminance of the backlight to 8000 cd / m 2 or more. . From the viewpoint of the visibility of the liquid crystal display device, the higher the luminance of the backlight, the better. However, when the function exceeds 100,000 cd / m 2 , the cooling cost of the panel increases.
- the colored resin composition is applied on a substrate, dried, and then analyzed by the following analysis method.
- the analysis of the pigment can be carried out using laser Raman (for example, Ramanor T-64000 manufactured by HOLIBA Jobin Yvon). Analysis of the quenching agent, chain transfer agent, sensitizer and the like can be measured using FT-IR (for example, FT-IR MICROSCOPE manufactured by SPECTR-TECH).
- detection can be performed with high accuracy by combining a collection method such as centrifugation, filtration, GPC fractionation, or the like, or a plurality of analysis methods as necessary.
- the transparent electrode layer and the protective film layer of the color filter substrate are removed by surface polishing, the colored resin composition is exposed, and an analysis sample is prepared. After collecting the purator, it can be carried out in the same manner as described above.
- Evaluation of the colored resin composition in the examples was performed by the following method.
- the non-photosensitive colored resin composition After apply
- a positive resist was coated and dried by heating at 90 ° C. for 10 minutes. Subsequently, after exposure at 100 mJ / cm 2 through a positive photomask, development was performed with 1.0 mass percent tetramethylammonium solution to form a desired pattern. After the positive resist was peeled off with methyl cellosolve acetate, heat curing was performed at 230 ° C. for 30 minutes.
- the colored resin composition was applied on the substrate and then dried by heating at 90 ° C. for 10 minutes.
- the obtained colored resin composition coating film was exposed to 100 mJ through a negative photomask, and then developed with a 0.3 mass percent tetramethylammonium solution to form a desired pattern. . Subsequently, heat curing was performed at 230 ° C. for 30 minutes.
- a red pixel and a blue pixel were respectively produced on the same substrate using the red resin composition and the blue resin group composition. Thereafter, a transparent electrode was formed to obtain a color filter substrate having green pixels, blue pixels, and red pixels.
- the green pixel of this color filter substrate was measured for transmittance with microscopic light in the same manner as described above (initial transmittance evaluation), and the obtained Y value was defined as Y0.
- An array substrate was produced by forming TFT elements, transparent electrodes and the like on alkali-free glass.
- a polyimide alignment film was formed on each of the color filter substrate prepared in (1) and the array substrate, and a rubbing treatment was performed.
- a sealant kneaded with microrods was printed on the array substrate, and a bead spacer having a thickness of 6 ⁇ m was sprayed, and then the array substrate and the color filter substrate were bonded together.
- nematic liquid crystal (“Rixon” JC-5007LA manufactured by Chisso) from the injection port provided in the seal part
- a polarizing film is bonded to both sides of the liquid crystal cell so that the polarization axis is perpendicular to obtain a liquid crystal panel. It was.
- a white LED backlight composed of a blue LED and a YAG phosphor was attached to this liquid crystal panel, and a TAB module, a printed board, etc. were mounted to produce a liquid crystal display device.
- a white LED backlight with a driving power adjusted and a luminance of 5000 to 20000 cd / m 2 was used.
- the colored resin composition is applied onto a glass substrate, dried at 90 ° C. for 10 minutes, and the exposure amount is 10, 20, 30, 40, 50 in terms of i-line, respectively, through a photomask having a 50 ⁇ m line & space pattern. , 100, 200, 400 mJ / cm 2 , the exposure time was adjusted, and ultraviolet exposure was performed.
- the gap between the substrate and the photomask was 25 ⁇ m.
- the exposed substrate was shower-developed in a 0.2 mass% tetramethylammonium hydroxide aqueous solution at 23 ° C. for 60 seconds, and then washed with pure water. Heating was performed at 230 ° C. for 30 minutes.
- a colored resin composition was applied on a glass substrate under the same conditions as described above, and the entire surface was exposed at 400 mJ / cm 2 in terms of exposure amount i-line, and then heated at 230 ° C. for 30 minutes without development.
- a substrate was prepared.
- the film thickness measurement of a 50 micrometer line pattern was performed.
- the exposure amount at which a film thickness of 90% or more remained was determined.
- the film thickness was measured with “Surface Rough Profile Measuring Machine Surfcom (registered trademark) 1400” manufactured by Tokyo Seimitsu Co., Ltd.
- the minimum exposure amount with a film thickness of 90% or more remaining was defined as sensitivity. Judgment was made according to the following criteria.
- CI Pigment Green 58 (“FASTGEN (registered trademark) Green A110” manufactured by DIC Corporation), 75 g of a polymer dispersant (“BYK-LPN6919” manufactured by BYK Chemie, 60% by mass solution), binder polymer (manufactured by Daicel Chemical, “Cyclo” Mer (registered trademark) P ′′, ACA 250, 45 mass% solution) 100 g and propylene glycol monomethyl ether (PMA) 675 g were mixed to prepare a slurry.
- FASTGEN registered trademark
- BYK-LPN6919 manufactured by BYK Chemie
- binder polymer manufactured by Daicel Chemical, “Cyclo” Mer (registered trademark) P ′′, ACA 250, 45 mass% solution
- PMA propylene glycol monomethyl ether
- the beaker containing the slurry was connected with a dyno mill and a tube, and zirconia beads having a diameter of 0.5 mm were used as media, and dispersion treatment was performed for 8 hours at a peripheral speed of 14 m / s. It was created.
- Pigment Yellow 138 Dispersion (D-2) was made by connecting the beaker containing the slurry with a dyno mill and a tube, using a zirconia bead with a diameter of 0.5 mm as a medium, and dispersing for 8 hours at a peripheral speed of 14 m / s. It was created.
- Pigment Yellow 150 (“Chromofine (registered trademark) Yellow 6266EC” manufactured by Dainichi Seika Co., Ltd.)
- 75 g of a polymer dispersant (“BYK-LPN6919” manufactured by BYK Chemie, 60% by mass solution), binder polymer (manufactured by Daicel Chemical Industries) , “Cyclomer (registered trademark) P”, ACA250, 45 mass% solution) 100 g and propylene glycol monomethyl ether (PMA) 675 g were mixed to prepare a slurry.
- Pigment Yellow 150 Dispersion (D-3) was made by connecting the beaker containing the slurry with a dyno mill and a tube, and using a zirconia bead with a diameter of 0.5 mm as the medium and dispersing at a peripheral speed of 14 m / s for 8 hours. It was created.
- Pigment Yellow 185 (BASF “Paliotol (registered trademark) Yellow D1155”)
- 75 g of a polymer dispersant BYK-LPN6919, manufactured by BYK Chemie, 60% by mass solution
- binder polymer manufactured by Daicel Chemical, “Cyclomer (registered) (Trademark) P ′′, ACA250, 45 mass% solution) 100 g and propylene glycol monomethyl ether (PMA) 675 g were mixed to prepare a slurry.
- PMA propylene glycol monomethyl ether
- Pigment Yellow 185 Dispersion (D-5) was made by connecting the beaker containing the slurry with a dyno mill and a tube, and using a zirconia bead with a diameter of 0.5 mm as a medium and dispersing at a peripheral speed of 14 m / s for 8 hours. It was created.
- Example 1 (Creation of colored resin composition) 36.84 g of D-1 above, 24.56 g of D-2 above, Cyclomer (registered trademark) P1.51 g, DPHA (dipentaerythritol hexaacrylate) reactive monomer (“Kayarad (registered trademark) DPHA” manufactured by Nippon Kayaku Co., Ltd.) ) 4.59 g, quencher (“9-ethyl-3-nitrocarbazole” (purity 98%) manufactured by Sigma-Aldrich) 0.29 g and PMA 32.21 g were added.
- a colored resin composition of Pigment Yellow 138 60/40 was produced.
- the obtained colored resin composition was evaluated according to the above evaluation method at a backlight luminance of 10,000 cd / m 2 .
- the initial transmittance was good at 51.0.
- the transmittance retention was as good as 84%.
- Example 2 A colored resin composition was prepared in exactly the same manner as in Example 1, except that the quencher 9-ethyl-3-nitrocarbazole in Example 1 was replaced with a nitrocarbazole-based initiator of the following formula (3). .
- the initial transmittance of the obtained colored resin composition was 51.0, which was good.
- the transmittance retention was a good value of 84%.
- the required exposure amount showed 40 mJ / cm ⁇ 2 > and the favorable characteristic. From this, it can be said that the initiator having a nitrocarbazole moiety has both an effect of a quencher and an effect as a photopolymerization initiator.
- Comparative Example 1 A colored resin composition was prepared in exactly the same manner as in Example 1 except that no deactivator was added. Although the initial transmittance of the obtained colored resin composition was good at 51.0, the transmittance retention after the weather resistance evaluation at a backlight luminance of 10,000 cd / m 2 was 74%, which was insufficient. It was.
- Comparative Example 2 A colored resin composition was prepared in exactly the same manner as in Example 1, except that 9-ethyl-3-nitrocarbazole was replaced with a hindered amine light stabilizer (“TINUVIN® 770DF” manufactured by BASF). Although the initial transmittance of the obtained colored resin composition is good at 51.0, the luminance retention after the weather resistance evaluation at a backlight luminance of 10,000 cd / m 2 is 77%, which is relative to that of Comparative Example 1. Although there was a slight improvement effect, it was insufficient.
- TINUVIN® 770DF hindered amine light stabilizer
- Comparative Example 3 A colored resin composition was prepared in exactly the same manner as in Example 1 except that 9-ethyl-3-nitrocarbazole was replaced with carbazole of the following formula. Although the initial transmittance of the obtained colored resin composition was good at 51.0, the transmittance retention after the weather resistance evaluation was 74%, which was insufficient. That is, it can be said that carbazole to which a nitro group is not added does not exhibit an effect as a deactivator.
- Example 4 Except that the deactivator 9-ethyl-3-nitrocarbazole in Example 1 was replaced with a carbazole-based initiator of the following formula having no nitro group (“OXE02” manufactured by BASF), exactly the same as Example 1.
- a colored resin composition was prepared. The initial transmittance of the obtained colored resin composition was good at 51.0. When the weather resistance was evaluated at a backlight luminance of 10,000 cd / m 2 , the transmittance retention was 74%, which was insufficient. Therefore, it can be said that a carbazole initiator having no nitro group has no effect of a quencher.
- Example 5 Except that the deactivator 9-ethyl-3-nitrocarbazole in Example 1 was replaced with a carbazole-based initiator of the following formula having no nitro group (“N1919” manufactured by ADEKA), it was exactly the same as Example 1.
- a colored resin composition was prepared. The initial transmittance of the obtained colored resin composition was good at 51.0. Further, the transmittance retention ratio at a backlight luminance of 10,000 cd / m 2 was 74%, which was an insufficient value. Therefore, it can be said that a carbazole initiator having no nitro group has no effect of a quencher.
- Example 3 In Example 2, instead of Pigment Green 58, Pigment Green 59 of the same polyhalogenated zinc phthalocyanine was used, except that the ratio of Pigment Green 59 and Pigment Yellow 138 was as shown in Table 2. A colored resin composition was prepared and evaluated in exactly the same manner. The initial transmittance was a good value of 50.5. Moreover, when the transmittance
- Example 4 A colored resin composition was prepared in exactly the same manner as in Example 2 except that Pigment Yellow 185 was used instead of Pigment Yellow 138 in Example 2 and the compounding ratio was as shown in Table 2, and the backlight luminance was 10,000 cd. It was evaluated in / m 2 (example 4).
- a colored resin composition was prepared and evaluated in exactly the same manner as in Example 3 except that Pigment Yellow 185 was used instead of Pigment Yellow 138 in Example 3 and the blending ratio was as shown in Table 2.
- Example 5 The initial transmittance was 52.0 (Example 4) and 51.4 (Example 5), which were very good values.
- Example 2 a colored resin composition was prepared and evaluated in exactly the same manner as in Example 2 except that Pigment Yellow 150 was further blended and the blending ratio was as shown in Table 2. As the ratio of Pigment Yellow 138 decreased, the initial transmittance was 50.5 (Example 6), 50.0 (Example 7), and 49.5 (Example 8). It was within the range. Moreover, when the transmittance
- luminance was 10000 cd / m ⁇ 2 >, 90% (Example 6), 92% (Example 7), and 96% (Example 8) showed a very favorable value. It was. Further, when the photosensitive properties were evaluated, all had sufficient sensitivity of 40 mJ / cm 2 .
- polyhalogenated zinc phthalocyanine and C.I. I. When the total content of pigment yellow 138 and the initial transmittance were compared, polyhalogenated zinc phthalocyanine and C.I. I. It can be said that the initial transmittance is high when the total content of Pigment Yellow 138 is 43% by mass or more.
- Examples 9, 10 In addition to the quencher of the general formula (3), a chain transfer agent (Karenz (registered trademark) MT PE-1 manufactured by Showa Denko KK (pentaerythritol tetrakis (3-mercaptopropionate): Example 9), (Showa Denko Co., Ltd. Karenz (registered trademark) MT NR-1 (1,3,5 tris (3-mercaptobutyloxyethyl) -1,3,5-triazine-2,4,6 (1H, 3H, 5H) -trione)): A colored resin composition was prepared and evaluated in the same manner as in Example 2 except that Example 10) was added.
- Karenz (registered trademark) MT NR-1 (1,3,5 tris (3-mercaptobutyloxyethy
- Example 11 In addition to the quencher of general formula (3), a sensitizer (DETX-S (2,4-diethylthioxanthen-9-one) manufactured by Nippon Kayaku Co., Ltd.) was added, and Example 2 A colored resin composition was prepared and evaluated in exactly the same manner, and the initial transmittance and the backlight retention at 10,000 cd / m 2 were good, and the sensitivity was very high and good. Therefore, it can be said that the sensitizer can improve only the sensitivity without impairing other properties.
- a sensitizer DETX-S (2,4-diethylthioxanthen-9-one manufactured by Nippon Kayaku Co., Ltd.
- Example 12 A colored resin composition was prepared and evaluated in exactly the same manner as in Example 2 except that the colorant was as shown in Table 2. When the transmittance retention was evaluated at a backlight luminance of 10,000 cd / m 2 , it was 100% and sufficient.
- Comparative Example 6 A colored resin composition was prepared and evaluated in exactly the same manner as in Comparative Example 1 except that the backlight luminance was 20000 cd / m 2 . As the backlight luminance increased, the luminance retention rate further decreased to 70%.
- Example 13 A colored resin composition was prepared and evaluated in exactly the same manner as in Example 2 except that the backlight luminance was 20000 cd / m 2 .
- the luminance retention rate was slightly reduced to 80%, but it was a value that could be used practically.
- Example 14 A colored resin composition was prepared and evaluated in exactly the same manner as in Example 12 except that the backlight luminance was 20000 cd / m 2 . Although there was a slight decrease in luminance retention, it was a very good value.
- Comparative Examples 7 and 8 A colored resin composition was prepared and evaluated in exactly the same manner as in Example 14, except that the initiator was replaced with initiators OXE02 (Comparative Example 7) and N1919 (Comparative Example 8) having no nitro group. The luminance retention rate was significantly lowered and was insufficient.
- Reference Examples 1-5 Reference Examples 1 to 5 were carried out in the same manner as Example 14, Example 2, Example 4, Comparative Example 7 and Comparative Example 8 except that the backlight luminance was set to 5000 cd / m 2 . Since the backlight luminance was low, the luminance retention rate was high. From this, it can be said that when the backlight luminance is low, the luminance is hardly lowered in the first place.
- Y138, Y185 / yellow pigment represents C.I. I.
- the total content of Pigment Yellow 138 and Pigment Yellow 185 is shown.
- “Colorant concentration” indicates the total content of polyhalogenated zinc phthalocyanine and yellow pigment, with the total content of polyhalogenated zinc phthalocyanine, yellow pigment, binder resin, reactive monomer and dispersant being 100% by mass.
- Green pigment, Y138 / resin is a polyhalogenated zinc phthalocyanine, C.I. I. Pigment Yellow 138, Binder Resin, Reactive Monomer and Dispersant in a total content of 100% by mass, polyhalogenated zinc phthalocyanine and C.I. I. The total content of Pigment Yellow 138 was shown.
- the colored resin composition of the present invention can be suitably used as a colored resin composition for forming pixels of a color filter substrate used in a liquid crystal display device.
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Abstract
Description
アルキル基、アリール基、アリールアルキル基および複素環基は、さらにOR21、COR21、SR21、NR22R23、-NCOR22-OCOR23、CN、ハロゲン原子、-CR21=CR22R23または-CO-CR21=CR22R23で置換されていてもよい。
アルキル基、アリール基、アリールアルキル基および複素環基は、さらにOR21、COR21、SR21、NR22R23、-NCOR22-OCOR23、CN、ハロゲン原子、-CR21=CR22R23または-CO-CR21=CR22R23で置換されていてもよい。
(初期透過率評価)
着色樹脂組成物をガラス基板上に塗布し、90℃10分間乾燥し、露光量i線40mJ/cm2で全面露光した後、230℃30分間加熱を行った。下記の各実施例、比較例において形成した緑色画素の膜厚は表2に示した。得られた着色樹脂組成物塗膜を、大塚電子製顕微分光測定器”LCF-100MA“を用いてC光源で測定を行い、CIE1931規格に基づくxy色度空間でのy-Yプロットにおいて、x=0.265、y=0.629の時のY値を求め、初期透過率とした。次の基準で評価を行った。
A:初期透過率が51以上
B:初期透過率が49を超え、51未満
C:初期透過率が49以下。
(1)カラーフィルタ作製
ブラックマトリックスを作製したガラス基板上に、以下のようにして、本発明の着色樹脂組成物を用いて緑色画素を形成した。
無アルカリガラス上にTFT素子、透明電極等を形成させてアレイ基板を作製した。(1)で作成したカラーフィルタ基板と該アレイ基板に、それぞれポリイミド配向膜を形成し、ラビング処理を行った。アレイ基板にマイクロロッドを練り込んだシール剤を印刷し、6μmの厚さのビーズスペーサーを散布した後、アレイ基板とカラーフィルタ基板を貼り合わせた。シール部に設けられた注入口からネマティック液晶(チッソ製“リクソン”JC-5007LA)を注入した後、液晶セルの両面に偏光フィルムを偏光軸が垂直になるようにして貼り合わせ、液晶パネルを得た。この液晶パネルに、青色LEDとYAG蛍光体からなる白色LEDバックライトを取り付け、TABモジュール、プリント基板等を実装し液晶表示装置を作製した。白色LEDバックライトは、駆動電力を調整し、輝度を5000~20000cd/m2のものを用いた。
液晶表示装置をバックライト点等状態で60℃60%の恒温高湿槽に100時間投入した。その後、パネルを解体し、緑色画素を前記と同様にして顕微分光で測定し、得られたY値をY1とした。Y1/Y0を透過率保持率とし次の基準で評価を行った。
A:透過率保持率が90%以上
B:透過率保持率が80%以上~90%未満
C:透過率保持率が80%未満。
着色樹脂組成物をガラス基板上に塗布し、90℃10分間乾燥し、50μmのライン&スペースパターンを持つフォトマスクを介して、露光量がそれぞれi線換算で10、20、30、40、50、100、200、400mJ/cm2となるように、露光時間を調整し、紫外線露光を行った。基板とフォトマスクのギャップは25μmとした。
A:感度が30mJ/cm2以下
B:感度が30mJ/cm2より大きく400mJ/cm2以下
C:感度が400mJ/cm2より大きい
非感光:評価なし
(着色剤分散液の作成)
C.I.ピグメントグリーン58(DIC(株)製 “FASTGEN(登録商標)Green A110”)150g、高分子分散剤(ビックケミー製“BYK-LPN6919”、60質量%溶液)75g、バインダーポリマー(ダイセル化学製、“サイクロマー(登録商標)P”、ACA250、45質量%溶液)100g、プロピレングリコールモノメチルエーテル(PMA)675gを混合してスラリーを作製した。スラリーを入れたビーカーをダイノーミルとチューブでつなぎ、メディアとして直径0.5mmのジルコニアビーズを使用して、周速14m/sで8時間の分散処理を行い、ピグメントグリーン58分散液(D-1)を作成した。
(着色樹脂組成物の作成)
上記D-1 36.84g、上記D-2 24.56g、サイクロマー(登録商標)P1.51g、DPHA(ジペンタエリスリトールヘキサアクリレート)反応性モノマー(日本化薬製 “カヤラッド(登録商標)DPHA”)4.59g、失活剤(シグマアルドリッチ製“9-エチル-3-ニトロカルバゾール”(純度98%)) 0.29g、PMA32.21gを添加し、C.I.ピグメントグリーン58/C.I.ピグメントイエロー138=60/40の着色樹脂組成物を作製した。
実施例1中の失活剤9-エチル-3-ニトロカルバゾールを下式(3)のニトロカルバゾール系開始剤に代えたこと以外は、実施例1と全く同様にして着色樹脂組成物を作成した。得られた着色樹脂組成物の初期透過率は51.0で良好であった。またバックライト輝度が10000cd/m2で耐候性評価を行った結果、透過率保持率は84%と良好な値を示した。さらに感光性評価を行ったところ、必要露光量が40mJ/cm2と良好な特性を示した。このことからニトロカルバゾール部位を持つ開始剤は、失活剤の効果と光重合開始剤としての効果を併せ持っているといえる。
失活剤を添加しない以外は実施例1と全く同様にして、着色樹脂組成物を作成した。得られた着色樹脂組成物の初期透過率は51.0で良好であるものの、バックライト輝度が10000cd/m2での耐候性評価後の透過率保持率は74%と不十分なものであった。
9-エチル-3-ニトロカルバゾールをヒンダートアミン光安定剤(BASF製 “TINUVIN(登録商標)770DF”)に代えた以外は、実施例1と全く同様にして、着色樹脂組成物を作成した。得られた着色樹脂組成物の初期透過率は51.0で良好であるものの、バックライト輝度が10000cd/m2での耐候性評価後の輝度保持率は77%と、比較例1に対してわずかな改良効果はあるものの不十分であった。
9-エチル-3-ニトロカルバゾールを下式のカルバゾールに代えた以外は、実施例1と全く同様にして、着色樹脂組成物を作成した。得られた着色樹脂組成物の初期透過率は51.0で良好であるものの、耐候性評価後の透過率保持率は74%と不十分なものであった。すなわちニトロ基が付加されていないカルバゾールは失活剤として効果を発揮しないといえる。
実施例1中の失活剤9-エチル-3-ニトロカルバゾールをニトロ基を持たない下式のカルバゾール系開始剤(BASF製“OXE02”)に代えたこと以外は、実施例1と全く同様にして着色樹脂組成物を作成した。得られた着色樹脂組成物の初期透過率は51.0で良好あった。またバックライト輝度が10000cd/m2での耐候性評価を行ったところ透過率保持率は74%と不十分な値を示した。このことからニトロ基を持たないカルバゾール開始剤は、失活剤の効果がないといえる。
実施例1中の失活剤9-エチル-3-ニトロカルバゾールをニトロ基を持たない下式のカルバゾール系開始剤(ADEKA製“N1919”)に代えたこと以外は、実施例1と全く同様にして着色樹脂組成物を作成した。得られた着色樹脂組成物の初期透過率は51.0で良好あった。またバックライト輝度が10000cd/m2での透過率保持率は74%と不十分な値を示した。このことからニトロ基を持たないカルバゾール開始剤は、失活剤の効果がないといえる。
実施例2において、ピグメントグリーン58の代わりに、同じくポリハロゲン化亜鉛フタロシアニンのピグメントグリーン59を用い、ピグメントグリーン59およびピグメントイエロー138の比率を、表2に示すようにした以外は、実施例2と全く同様にして着色樹脂組成物を作成し、評価した。初期透過率が50.5と良好な値を示した。またバックライト輝度が10000cd/m2での透過率保持率を評価したところ89%と実用上十分な特性を有していた。このことからポリハロゲン化亜鉛フタロシアニンとピグメントイエロー138と一般式(1)の化合物の組み合わせは、初期透過率が極めて良好であり、透過率保持率が良好であるといえる。
実施例2においてピグメントイエロー138の代わりにピグメントイエロー185を用い、配合比を表2に示すようにした以外は、実施例2と全く同様にして着色樹脂組成物を作成し、バックライト輝度が10000cd/m2で評価した(実施例4)。また実施例3においてピグメントイエロー138の代わりにピグメントイエロー185を用い、配合比を表2に示すようにした以外は、実施例3と全く同様にして着色樹脂組成物を作成し、評価した(実施例5)。初期透過率が52.0(実施例4)、51.4(実施例5)と極めて良好な値を示した。またバックライト輝度が10000cd/m2での透過率保持率を評価したところ、93%(実施例4)、93%(実施例5)と極めて良好な値をしめした。このことからポリハロゲン化亜鉛フタロシアニンとピグメントイエロー185と一般式(1)の化合物の組み合わせは、初期透過率と透過率保持率が極めて良好であるといえる。
実施例2において、ピグメントイエロー150をさらに配合し、配合比を、表2に示すようにした以外は、実施例2と全く同様にして着色樹脂組成物を作成し、評価した。ピグメントイエロー138の比率が低下するに従い、初期透過率が50.5(実施例6)、50.0(実施例7)、49.5(実施例8)と低下の傾向が見られたが実用範囲内であった。またバックライト輝度が10000cd/m2での透過率保持率を評価したところ、90%(実施例6)、92%(実施例7)、96%(実施例8)と極めて良好な値を示した。さらに感光特性を評価したところ、いずれも40mJ/cm2と十分な感度を有していた。
一般式(3)の失活剤に加えて、連鎖移動剤(昭和電工(株)製カレンズ(登録商標)MT PE-1 (ペンタエリスリトールテトラキス(3-メルカプトプロピオネート):実施例9)、(昭和電工(株)製カレンズ(登録商標)MT NR-1(1,3,5トリス(3-メルカプトブチルオキシエチル)-1,3,5-トリアジン-2,4,6(1H,3H,5H)-トリオン)):実施例10)をそれぞれ添加した以外は、実施例2と全く同様にして着色樹脂組成物を作成し、評価した。いずれも初期透過率とバックライト輝度が10000cd/m2での透過率保持率が良好であり、かつ感度が極めて高く良好であった。このことから連鎖移動剤は他の特性を損なわずに感度のみ向上させることができるといえる。
一般式(3)の失活剤に加えて、増感剤(日本化薬(株)製DETX-S (2,4-ジエチルチオキサンテン-9-オン)を添加した以外は、実施例2と全く同様にして着色樹脂組成物を作成し、評価した。初期透過率とバックライト輝度が10000cd/m2での透過率保持率が良好であり、かつ感度が極めて高く良好であった。このことから増感剤は他の特性を損なわずに感度のみ向上させることができるといえる。
着色剤を表2に示すようにした以外は、実施例2と全く同様にして着色樹脂組成物を作成し、評価した。バックライト輝度が10000cd/m2での透過率保持率を評価したところ、100%と充分なものであった。
バックライト輝度を20000cd/m2とした以外は比較例1と全く同様にして着色樹脂組成物を作成し、評価した。バックライト輝度の増大に応じて、輝度保持率は70%とさらに低下していた。
バックライト輝度を20000cd/m2とした以外は実施例2と全く同様にして着色樹脂組成物を作成し、評価した。輝度保持率は80%と、やや低下したが、実用上充分に使用できる値であった。
バックライト輝度を20000cd/m2とした以外は実施例12と全く同様にして着色樹脂組成物を作成し、評価した。若干の輝度保持率の低下がみられたが,非常に良好な値であった。
開始剤をニトロ基を持たない開始剤OXE02(比較例7)、N1919(比較例8)にそれぞれ代えた以外は、実施例14と全く同様にして着色樹脂組成物を作成し、評価した。輝度保持率が大幅に低下し、不十分な値であった。
バックライト輝度を5000cd/m2とした以外は、実施例14、実施例2、実施例4、比較例7および比較例8と同様にして、参考例1~5を実施した。バックライト輝度が低いことにより、輝度保持率が高くなった。このことからバックライト輝度が低い場合には、そもそも輝度低下が起こりにくいと言える。
Claims (15)
- ポリハロゲン化亜鉛フタロシアニン、黄色顔料、バインダー樹脂および下記一般式(1)で表される化合物を含有し、該黄色顔料がC.I.ピグメントイエロー138およびC.I.ピグメントイエロー185から選ばれた顔料である着色樹脂組成物;
R4は、炭素原子数1~20のアルキル基、炭素原子数6~30のアリール基または炭素原子数7~30のアリールアルキル基を表し、R4は、隣接するベンゼン環とともに環を形成していてもよい;
R5およびR6は、それぞれ独立に、炭素原子数1~20のアルキル基、炭素原子数1~20のアルコキシ基、炭素原子数6~30のアリール基、炭素原子数6~30のアリールオキシ基、炭素原子数7~30のアリールアルキル基、炭素原子数7~30のアリールアルキルオキシ基、炭素原子数2~20の複素環基、CNまたはハロゲン原子を表し、aおよびbは、それぞれ独立に、0~3である;
R2は、炭素原子数1~20のアルキル基、炭素原子数6~30のアリール基、炭素原子数7~30のアリールアルキル基、炭素原子数2~20の複素環基またはCNを表し、アルキル基、アリール基、アリールアルキル基および複素環基の水素原子の少なくとも一部がOR21、COR21、SR21、NR22R23、-NCOR22-OCOR23、CN、ハロゲン原子、-CR21=CR22R23または-CO-CR21=CR22R23で置換されていてもよい;
R21、R22およびR23は、それぞれ独立に、水素原子、炭素原子数1~20のアルキル基、炭素原子数1~20のアルケニル基、炭素原子数6~30のアリール基、炭素原子数7~30のアリールアルキル基または炭素原子数2~20の複素環基を表す;
R3は、炭素原子数1~20のアルキル基、炭素原子数1~20のアルコキシ基、炭素原子数6~30のアリール基、炭素原子数6~30のアリールオキシ基、炭素原子数7~30のアリールアルキル基、炭素原子数7~30のアリールアルキル基、炭素原子数7~30のアリールアルキルオキシ基または炭素原子数2~20の複素環基を表し、これらの基の水素原子の少なくとも一部は、さらにハロゲン原子で置換されていてもよい;
前記において、アルキル基は直鎖状でも分岐状でも環状でもよく、アルキル鎖中に不飽和結合、エーテル結合、チオエーテル結合、エステル結合、チオエステル結合、アミド結合およびウレタン結合から選ばれた結合を1~5個含んでもよい。 - 前記黄色顔料が、C.I.ピグメントイエロー138を含み、反応性モノマーおよび分散剤をさらに含み、かつ、ポリハロゲン化亜鉛フタロシアニン、C.I.ピグメントイエロー138、バインダー樹脂、反応性モノマーおよび分散剤の合計含有量を100質量%として、ポリハロゲン化亜鉛フタロシアニンおよびC.I.ピグメントイエロー138の合計含有量が43~55質量%である請求項1記載の着色樹脂組成物。
- ポリハロゲン化亜鉛フタロシアニンが、C.I.ピグメントグリーン58およびC.I.ピグメントグリーン59から選ばれた1種以上である請求項1から3のいずれか一項記載の着色樹脂組成物。
- さらに、C.I.ピグメントイエロー150を含み、黄色顔料の合計含有量を100質量%として、C.I.ピグメントイエロー138およびピグメントイエロー185の合計含有量が20~80質量%である請求項1から4のいずれか一項記載の着色樹脂組成物。
- さらに連鎖移動剤を含む、請求項1から5のいずれか一項記載の着色樹脂組成物。
- さらに増感剤を含む、請求項1から6のいずれか一項記載の着色樹脂組成物。
- 請求項1から7のいずれか一項記載の着色樹脂組成物を用いて形成された画素を有する、カラーフィルタ基板。
- カラーフィルタ基板と対向基板とが貼合され、両者の間に液晶化合物が充填され、バックライトが取り付けられた液晶表示装置であって、該カラーフィルタ基板が、ポリハロゲン化亜鉛フタロシアニン、黄色顔料、バインダー樹脂および下記一般式(1)で表される化合物を含有する画素を有し、該黄色顔料がC.I.ピグメントイエロー150、C.I.ピグメントイエロー138およびC.I.ピグメントイエロー185からなる群より選ばれる少なくとも1種であり、かつ、該バックライトの輝度が8000~100000cd/m2である液晶表示装置;
R4は、炭素原子数1~20のアルキル基、炭素原子数6~30のアリール基または炭素原子数7~30のアリールアルキル基を表し、R4は、隣接するベンゼン環とともに環を形成していてもよい;
R5およびR6は、それぞれ独立に、炭素原子数1~20のアルキル基、炭素原子数1~20のアルコキシ基、炭素原子数6~30のアリール基、炭素原子数6~30のアリールオキシ基、炭素原子数7~30のアリールアルキル基、炭素原子数7~30のアリールアルキルオキシ基、炭素原子数2~20の複素環基、CNまたはハロゲン原子を表し、aおよびbは、それぞれ独立に、0~3である;
R2は、炭素原子数1~20のアルキル基、炭素原子数6~30のアリール基、炭素原子数7~30のアリールアルキル基、炭素原子数2~20の複素環基またはCNを表し、アルキル基、アリール基、アリールアルキル基および複素環基の水素原子の少なくとも一部がOR21、COR21、SR21、NR22R23、-NCOR22-OCOR23、CN、ハロゲン原子、-CR21=CR22R23または-CO-CR21=CR22R23で置換されていてもよい;
R21、R22およびR23は、それぞれ独立に、水素原子、炭素原子数1~20のアルキル基、炭素原子数1~20のアルケニル基、炭素原子数6~30のアリール基、炭素原子数7~30のアリールアルキル基または炭素原子数2~20の複素環基を表す;
R3は、炭素原子数1~20のアルキル基、炭素原子数1~20のアルコキシ基、炭素原子数6~30のアリール基、炭素原子数6~30のアリールオキシ基、炭素原子数7~30のアリールアルキル基、炭素原子数7~30のアリールアルキル基、炭素原子数7~30のアリールアルキルオキシ基または炭素原子数2~20の複素環基を表し、これらの基の水素原子の少なくとも一部は、さらにハロゲン原子で置換されていてもよい;
前記において、アルキル基は直鎖状でも分岐状でも環状でもよく、アルキル鎖中に不飽和結合、エーテル結合、チオエーテル結合、エステル結合、チオエステル結合、アミド結合およびウレタン結合から選ばれた結合を1~5個含んでもよい。 - 前記ポリハロゲン化亜鉛フタロシアニンが、C.I.ピグメントグリーン58およびC.I.ピグメントグリーン59から選ばれた1種以上である請求項9または10記載の表示装置。
- 黄色顔料の合計含有量を100質量%として、C.I.ピグメントイエロー138およびピグメントイエロー185の合計含有量が20~80質量%である請求項9から11のいずれか一項記載の表示装置。
- 前記ポリハロゲン化亜鉛フタロシアニンがC.I.ピグメントグリーン59である請求項9から12のいずれか一項記載の表示装置。
- 前記黄色顔料がピグメントイエロー185である請求項13記載の表示装置。
- 前記着色樹脂組成物の着色剤の合計含有量を100質量%として、ポリハロゲン化亜鉛フタロシアニンの含有量が72質量%以上である、請求項9から14いずれか一項記載の表示装置。
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JP2019199491A (ja) * | 2018-05-14 | 2019-11-21 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
JP2020095194A (ja) * | 2018-12-14 | 2020-06-18 | 東洋インキScホールディングス株式会社 | カラーフィルタ用感光性着色組成物及びカラーフィルタ |
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WO2021199748A1 (ja) | 2020-03-30 | 2021-10-07 | 富士フイルム株式会社 | 組成物、膜及び光センサ |
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WO2023032545A1 (ja) | 2021-08-31 | 2023-03-09 | 富士フイルム株式会社 | 硬化物の製造方法、積層体の製造方法、及び、半導体デバイスの製造方法、並びに、処理液 |
WO2023054142A1 (ja) | 2021-09-29 | 2023-04-06 | 富士フイルム株式会社 | 組成物、樹脂、膜および光センサ |
KR20240044426A (ko) | 2021-08-20 | 2024-04-04 | 도레이 카부시키가이샤 | 감광성 조성물, 컬러 필터 기판, 지문 센서 및 표시 장치 |
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WO2022065006A1 (ja) | 2020-09-28 | 2022-03-31 | 富士フイルム株式会社 | 積層体の製造方法、アンテナインパッケージの製造方法、積層体及び組成物 |
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WO2022210175A1 (ja) | 2021-03-29 | 2022-10-06 | 富士フイルム株式会社 | 黒色感光性組成物、黒色感光性組成物の製造方法、硬化膜、カラーフィルタ、遮光膜、光学素子、固体撮像素子、ヘッドライトユニット |
KR20240044426A (ko) | 2021-08-20 | 2024-04-04 | 도레이 카부시키가이샤 | 감광성 조성물, 컬러 필터 기판, 지문 센서 및 표시 장치 |
WO2023032545A1 (ja) | 2021-08-31 | 2023-03-09 | 富士フイルム株式会社 | 硬化物の製造方法、積層体の製造方法、及び、半導体デバイスの製造方法、並びに、処理液 |
WO2023054142A1 (ja) | 2021-09-29 | 2023-04-06 | 富士フイルム株式会社 | 組成物、樹脂、膜および光センサ |
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JPWO2017164127A1 (ja) | 2019-01-31 |
CN108700809B (zh) | 2021-10-08 |
TW201802161A (zh) | 2018-01-16 |
US20190056662A1 (en) | 2019-02-21 |
KR20180124013A (ko) | 2018-11-20 |
JP7006267B2 (ja) | 2022-01-24 |
CN108700809A (zh) | 2018-10-23 |
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