WO2018182135A1 - Composition de résine photosensible bleue, filtre coloré produit à l'aide de celle-ci et dispositif d'affichage d'image - Google Patents
Composition de résine photosensible bleue, filtre coloré produit à l'aide de celle-ci et dispositif d'affichage d'image Download PDFInfo
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- WO2018182135A1 WO2018182135A1 PCT/KR2017/013933 KR2017013933W WO2018182135A1 WO 2018182135 A1 WO2018182135 A1 WO 2018182135A1 KR 2017013933 W KR2017013933 W KR 2017013933W WO 2018182135 A1 WO2018182135 A1 WO 2018182135A1
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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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
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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 blue photosensitive resin composition, a color filter manufactured using the same, and an image display device.
- the color filter is a thin film type optical component that extracts three colors of red, green, and blue from white light and makes them possible in fine pixel units.
- the size of one pixel is about tens to hundreds of micrometers.
- Such a color filter includes a black matrix layer formed in a predetermined pattern on a transparent substrate to shield the boundary between each pixel, and a plurality of colors (typically red (R), green (G) and The pixel units in which the three primary colors of blue (B) are arranged in a predetermined order are stacked in this order.
- Korean Patent Publication No. 2007-0094679 suggests that color reproducibility can be improved by having a color filter layer formed of quantum dots, and Korean Patent Publication No. 2009-0036373 uses a conventional color filter as a quantum dot phosphor. It is proposed that the display quality can be improved by improving the luminous efficiency by replacing the light emitting layer.
- the photosensitive resin composition developed to manufacture a color filter has not sufficiently satisfied the requirements such as development speed control, fine pattern formation, excellent optical efficiency and viewing angle to be sufficiently used in the process.
- the present invention is to control the development speed, to solve the problem caused by the process residue by eliminating the residue of the fine pattern, to improve the poor display, to implement a color filter, especially a self-luminous color filter to ensure excellent light efficiency and viewing angle It is an object of the present invention to provide a blue photosensitive resin composition capable of this, a color filter and an image display device manufactured using the same.
- the present invention provides a blue photosensitive resin composition comprising a scattering particle, a blue colorant, a binder resin, a cardo-based binder resin, a photoinitiator, a photopolymerizable compound, a thermosetting agent and a solvent, wherein the photopolymerizable compound comprises an alkylene oxide. It provides a blue photosensitive resin composition characterized by including a compound.
- the present invention also provides a color filter comprising a blue pattern layer made of the above-described blue photosensitive resin composition.
- the present invention is the color filter; And a light source emitting blue light.
- the present invention includes a photopolymerizable compound containing alkylene oxide in the blue photosensitive resin composition, to control the development speed, solve the problem caused by the process residue by eliminating the residue of the pattern, and poor display problems are improved
- the present invention provides a color filter in which the problem of resist non-developing is improved.
- it is possible to provide a high-quality self-luminous color filter having an excellent viewing angle by adjusting the taper.
- the blue photosensitive resin composition of the present invention may include a cardo-based binder resin, a photoinitiator, a photopolymerizable compound and a solvent as scattering particles, a blue colorant, and a binder resin, and in particular, the photopolymerizable compound may include ethylene oxide or propylene oxide.
- the color filter including the blue pattern layer prepared by using the blue photosensitive resin composition of the present invention can solve the problem caused by the residue on the process by controlling the development speed and eliminating the residue of the pattern. .
- a color filter in particular, a self-luminous color filter, in which a problem of poor display is improved and an issue of resist non-developing is improved.
- the scattering particles of the present invention may be a metal oxide having an average particle diameter of 10 to 1000 nm, more preferably when the average particle diameter is in the range of 30 to 500 nm. In this case, when the average particle diameter is less than the above range, sufficient scattering effect of the incident light cannot be expected, and when the average particle diameter is above the above range, the surface of the self-luminous layer of uniform quality cannot be obtained.
- the metal oxide is Li, Be, B, Na, Mg, Al, Si, K, Ca, Sc, V, Cr, Mn, Fe, Ni, Cu, Zn, Ga, Ge, Rb, Sr, Y, Mo, Cs, Ba, La, Hf, W, Tl, Pb, Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Ti, Sb, Sn, Zr, Nb, It may be an oxide including one metal selected from the group consisting of Ce, Ta, In, and combinations thereof.
- the scattering particles may be appropriately adjusted as necessary to the average particle diameter and the content in the entire composition to sufficiently improve the light emission intensity of the color filter.
- the scattering particles may be included in 0.1 to 50% by weight relative to the total weight of solids in the blue photosensitive resin, preferably 5 to 35% by weight.
- the scattering particles are in the above preferred range, the effect of increasing the light emission intensity can be obtained, and the stability of the composition can be ensured.
- examples of the blue pigment include compounds classified as pigments in the color index (Published by The society of Dyers and Colourists), and more specifically, the color index (CI) as follows.
- pigment of number is mentioned, It is not necessarily limited to these.
- Blue pigments are specifically described, for example, in C.I. Pigment blue 15: 3, 15: 4, 15: 6, 16, 21, 28, and 76, and the like.
- Pigment Blue 15: 3, Pigment Blue 15: 6, Pigment Blue 16 It is preferable to include at least 1 type selected from the group which consists of.
- the blue colorant of the present invention may further comprise a blue dye, which is a known dye which is described in a compound or dyeing note (color dyed yarn) classified as a dye in the color index (published by The Society of Dyers and Colourists). And dyes.
- a blue dye which is a known dye which is described in a compound or dyeing note (color dyed yarn) classified as a dye in the color index (published by The Society of Dyers and Colourists). And dyes.
- the said blue dye can be used individually or in combination of 2 or more types, respectively.
- the blue colorant of the present invention may further include a purple colorant as an additional colorant.
- the purple coloring agent may comprise at least one of a purple pigment and a purple dye, wherein the purple pigment is specifically C.I. Pigment violet 1, 14, 19, 23, 29, 32, 33, 36, 37 and 38, among which C.I. It is more preferred to include pigment violet 23.
- Purple dyes are specifically, C.I. Solvent violet, C.I. acid violet, C.I. acid violet, C.I. modanto violet, and the like, but are not limited thereto.
- the C.I. Solvent violet is C.I. Solvent violet 8, 9, 13, 14, 36, 37, 47 and 49, and the like. More preferably, solvent violet 13 is included.
- C.I. acid violet includes C.I. Acid violet 6B, 7, 9, 17, 19 and 66, and the like. More preferably, acid violet 66 is included.
- CI direct violet includes CI direct violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103 and 104. .
- the blue colorant may be used in an amount of 0.1 to 50% by weight, preferably 0.5 to 30% by weight, based on the total weight of solids in the blue photosensitive resin.
- content of the blue colorant satisfies the above range, it is possible to suppress the reflection of external light, to effectively exhibit the emission intensity of the color, and to ensure the stability of the viscosity.
- the blue colorant and the scattering particles are included even though the blue quantum dots are not included, thereby reducing the efficiency of the blue pixel of the color filter, particularly the self-luminous color filter.
- the binder resin of this invention contains cardo system binder resin.
- the cardo-based binder resin has reactivity and alkali solubility due to the action of light or heat and acts as a dispersion medium of the coloring material.
- the cardo-based binder resin contained in the blue photosensitive resin composition of the present invention is not limited as long as it is a resin that acts as a binder resin for scattering particles and is soluble in an alkaline developer used in the developing step for producing a color filter.
- the cardo-based binder resin of the present invention may include one or more of the compounds represented by Formulas 1-1 and 1-2.
- R 1 , R 2 , R 3 and R 4 are each independently, Is;
- X is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a hydroxyl group
- R 5 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
- the compound represented by Chemical Formula 1-1 may be synthesized by the compound represented by Chemical Formula 2-1, and the compound represented by Chemical Formula 1-2 may be synthesized using the compound represented by Chemical Formula 2-2. .
- the compound represented by Chemical Formula 1-1 may be synthesized by the compound represented by Chemical Formula 2-1, and the compound represented by Chemical Formula 1-2 may be synthesized using the compound represented by Chemical Formula 2-2. .
- the compound represented by Formula 1-1 is at least one of the compounds represented by Formula 1-1-1 and Formula 1-1-2, and the compound represented by Formula 1-2 is represented by Formula 1-2- 1 and one or more compounds represented by Formula 1-2-2.
- the cardo-based binder resin is 9,9-bis (3-cinnamic diester) fluorene (9,9-bis (3-cinnamic diester) fluorene), 9,9-bis (3- cinnamoyl, 4-hydride Hydroxyphenyl) fluorene (9,9-bis (3-cinnamoil, 4-hydroxyphenyl) fluorene), 9,9-bis (glycidyl methacrylate ether) fluorene (9,9-bis (glycidyl methacrylate ether) fluorene), 9,9-bis (3,4-dihydroxyphenyl) fluorene dinamic ester (9,9-bis (3,4-dihydroxyphenyl) fluorene dicinnamic ester), 3,6-diglycidyl meta Acrylate ether spiro (3,6-diglycidyl methacrylate ether spiro (fluorene-9,9-xantene)), 9,9-bis (3-ally
- It can be prepared by reacting with at least one selected from the group consisting of aromatic polyhydric carboxylic acid anhydrides such as pyromellitic anhydride, benzophenone tetracarboxylic acid dianhydride, biphenyltetracarboxylic acid dianhydride, and bitenyl ether tetracarboxylic acid dianhydride. It is not limited.
- aromatic polyhydric carboxylic acid anhydrides such as pyromellitic anhydride, benzophenone tetracarboxylic acid dianhydride, biphenyltetracarboxylic acid dianhydride, and bitenyl ether tetracarboxylic acid dianhydride. It is not limited.
- the present invention may further include an acrylic alkali-soluble resin as a binder resin.
- the acrylic alkali-soluble resin include a carboxyl group-containing monomer and a copolymer with another monomer copolymerizable with the monomer.
- a carboxyl group-containing monomer unsaturated carboxylic acids, such as unsaturated monocarboxylic acid, unsaturated polycarboxylic acid, such as unsaturated polyhydric carboxylic acid which has one or more carboxyl groups in molecules, such as unsaturated dicarboxylic acid and unsaturated tricarboxylic acid, are mentioned, for example. have.
- unsaturated monocarboxylic acid acrylic acid, methacrylic acid, crotonic acid, (alpha)-chloroacrylic acid, cinnamic acid etc. are mentioned, for example.
- unsaturated dicarboxylic acid a maleic acid, a fumaric acid, itaconic acid, a citraconic acid, a mesaconic acid, etc. are mentioned, for example.
- the unsaturated polyhydric carboxylic acid may be an acid anhydride, and specific examples thereof include maleic anhydride, itaconic anhydride and citraconic anhydride.
- the unsaturated polyhydric carboxylic acid may be mono (2-methacrylyloxyalkyl) ester thereof, for example, succinic mono (2-acryloyloxyethyl), succinic acid mono (2-methacryloyloxyethyl) And phthalic acid mono (2-acryloyloxyethyl), phthalic acid mono (2-methacryloyloxyethyl) and the like.
- the unsaturated polyhydric carboxylic acid may be mono (meth) acrylate of the sock end dicarboxy polymer, and examples thereof include? -Carboxypolycaprolactone monoacrylate and? -Carboxypolycaprolactone monomethacrylate. .
- carboxyl group-containing monomers can be used individually or in mixture of 2 or more types, respectively.
- styrene (alpha) -methylstyrene, o-vinyl toluene, m-vinyl toluene, p-vinyl toluene, p-chloro styrene, o-methoxy styrene, m-meth Oxy styrene, p-methoxy styrene, o-vinyl benzyl methyl ether, m-vinyl benzyl methyl ether, p-vinyl benzyl methyl ether, o-vinyl benzyl glycidyl ether, m-vinyl benzyl glycidyl ether, p- Aromatic vinyl compounds such as vinyl benzyl
- Unsaturated carboxylic acid esters 2-aminoethyl acrylate, 2-aminoethyl methacrylate, 2-dimethylaminoethyl acrylate, 2-dimethylaminoethyl methacrylate, 2-aminopropyl acrylate, 2-aminopropyl methacrylate, 2-dimethyl Unsaturated carboxyl such as aminopropyl acrylate, 2-dimethylaminopropyl methacrylate, 3-aminopropyl acrylate, 3-aminopropyl methacrylate, 3-dimethylaminopropyl acrylate and 3-dimethylaminopropyl methacrylate Acid aminoalkyl esters; Unsaturated carboxylic acid glycidyl esters such as glycidyl acrylate and glycidyl methacrylate; Carboxylic acid vinyl esters such as vinyl acetate, vinyl propionate, vinyl butyrate and vinyl benzoate; Un
- Unsaturated imides such as N-cyclohexylmaleimide; Aliphatic conjugated dienes such as 1,3-butadiene, isoprene and chloroprene; And monoacryloyl or monomethacryloyl groups at the terminal of the polymer molecular chain of polystyrene, polymethylacrylate, polymethylmethacrylate, poly-n-butylacrylate, poly-n-butylmethacrylate, polysiloxane. And macromonomers to have. These monomers can be used individually or in mixture of 2 or more types, respectively.
- bulky monomers such as monomers having a norbornyl skeleton, monomers having an adamantane skeleton, and monomers having a rosin skeleton as the other monomers copolymerizable with the carboxyl group-containing monomer are preferable because they tend to lower the dielectric constant.
- the acid value is preferably in the range of 20 to 200 (KOH mg / g). If the acid value is in the above range, the solubility in the developing solution is improved, so that the non-exposed part is easily dissolved and the sensitivity is increased, and as a result, the pattern of the exposed part remains at the time of development to improve the film remaining ratio.
- the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the acrylic polymer, and can usually be obtained by titration using an aqueous potassium hydroxide solution.
- the polystyrene reduced weight average molecular weight (hereinafter, simply referred to as 'weight average molecular weight') measured by gel permeation chromatography (GPC; tetrahydrofuran as an eluting solvent) is 2,000 to 200,000, preferably 3,000 to 100,000.
- GPC gel permeation chromatography
- Cardo binder resin or acrylic alkali-soluble resin is preferable.
- the molecular weight is in the above range, the hardness of the coating film is improved, the residual film ratio is high, the solubility of the non-exposed portion in the developer is excellent and the resolution tends to be improved, which is preferable.
- the molecular weight distribution [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the cardo-based binder resin and / or the acrylic alkali-soluble resin is preferably 1.0 to 6.0, and more preferably 1.5 to 6.0. If molecular weight distribution [weight average molecular weight (Mw) / number average molecular weight (Mn)] is 1.5-6.0, since developability is excellent, it is preferable.
- the binder resin of the present invention may use 5 to 85% by weight, preferably 5 to 60% by weight based on the total weight of solids in the blue photosensitive resin.
- the solubility in the developing solution is sufficient, and development residues are less likely to occur on the substrate of the non-pixel portion. It is preferable because this tends to be good.
- the photopolymerizable compound included in the blue photosensitive resin composition of the present invention is a compound that can be polymerized by the action of light and a photopolymerization initiator described below, and specifically, a photopolymerizable compound containing alkylene oxide, preferably ethylene oxide and / or propylene oxide. And a photopolymerizable compound containing a.
- a photopolymerizable compound added with ethylene oxide and / or propylene oxide is included, various problems that may occur due to process residues can be solved by controlling the development speed, eliminating the residues of the pattern, and improving display defects. It is possible to eliminate the resist non-development, and to adjust the taper, to form an excellent viewing angle, it is possible to manufacture a device of high quality image quality.
- the alkylene oxide modified pentaerythritol (meth) acrylate compound As a photopolymerizable compound containing the said alkylene oxide, the alkylene oxide modified pentaerythritol (meth) acrylate compound, the alkylene oxide modified dipentaerythritol (meth) acrylate compound, and the alkylene oxide modified trimetholpropane ( Meta) acrylate compounds, and alkylene oxide modified glycerin (meth) acrylate compounds, and more specifically, ethylene oxide modified trimetholpropane triacrylate, ethylene oxide modified dipentaerythritol hexaacrylate, and ethylene oxide.
- the alkylene oxide modified pentaerythritol (meth) acrylate compound As a photopolymerizable compound containing the said alkylene oxide, the alkylene oxide modified pentaerythritol (meth) acrylate compound, the alkylene oxide modified dipentaery
- Modified pentaerythritol tetraacrylate ethylene oxide modified pentaerythritol tetraacrylate, propylene oxide modified pentaerythritol tetraacrylate, ethoxylated pentaerythritol tetraacrylate, ethoxylated dipentaerythritol hex Oh, and the like Cri rate, propoxy federated pentaerythritol polyacrylate, propoxy federated dipentaerythritol hexa acridine rate, ethoxy federated glycerol triacrylate.
- the blue photosensitive resin composition of this invention may further contain the conventional photopolymerizable compound which does not contain an alkylene oxide.
- the photopolymerizable compound using the monofunctional monomer, bifunctional monomer, and other polyfunctional monomer which do not contain ethylene oxide and a propylene oxide is mentioned.
- the monofunctional monomers include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate and N-vinylpyrroli Money, etc.
- Specific examples of the bifunctional monomer include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, Bis (acryloyloxyethyl) ether of bisphenol A, 3-methylpentanediol di (meth) acrylate, etc. are mentioned.
- polyfunctional monomers include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, di Pentaerythritol hexa (meth) acrylate etc. are mentioned. Of these, bifunctional or higher polyfunctional monomers are preferably used.
- the photopolymerizable compound may be used in an amount of 5 to 50% by weight, preferably 5 to 30% by weight, based on the total weight of solids in the blue photosensitive resin. If the photopolymerizable compound is within the above range, there is no reduction in photosensitivity, sufficient strength of the film, no loss of pattern during development, good pattern construction even in the fine pattern portion, and tendency of smoothness of the resist. desirable.
- the photoinitiator used in the present invention initiates a radical reaction of the photosensitive resin composition, causes curing, improves sensitivity, and preferably contains an acetophenone-based compound.
- an acetophenone type compound for example, diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyl dimethyl ketal, 2-hydroxy-1- [4- (2 -Hydroxyethoxy) phenyl] -2-methylpropane-1-one, 1-hydroxycyclohexylphenyl ketone, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropane-1- On, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one, 2-hydroxy-2-methyl [4- (1-methylvinyl) phenyl] propane-1- Oligomers, etc.
- photoinitiators other than the said acetophenone series can be used in combination.
- Photopolymerization initiators other than the acetophenone series include active radical generators, sensitizers, and acid generators that generate active radicals by irradiation with light.
- an active radical generating agent a benzoin compound, a benzophenone type compound, a thioxanthone type compound, a triazine type compound, etc. are mentioned, for example.
- benzoin type compound benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoisobutyl ether, etc. are mentioned, for example.
- benzophenone type compound for example, benzophenone, methyl o-benzoyl benzoate, 4-phenylzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3 ', 4,4'- tetra ( t-butylperoxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone, etc. are mentioned.
- thioxanthone type compound 2-isopropyl thioxanthone, 4-isopropyl thioxanthone, 2, 4- diethyl thioxanthone, 2, 4- dichloro thioxanthone, 1-chloro-, for example 4-propoxy city oxanthone etc. are mentioned.
- Examples of the active radical generator include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,2, -bis (o-chlorophenyl) -4,4 ', 5,5'-tetra Phenyl-1,2'-biimidazole, 10-butyl-2-chloroacridone, 2-ethylanthraquinone, benzyl, 9,10-phenanthrenequinone, camphorquinone, methyl phenylglyoxylate, titanocene Compounds and the like can be used.
- Examples of the acid generator include 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate and 4-acetoxyphenyldimethylsulfonium p-toluenesulfo.
- a triazine photopolymerization initiator is also used as an acid generator.
- the photoinitiator may be included 0.1 to 30% by weight, preferably 0.3 to 20% by weight relative to the total weight of solids in the blue photosensitive resin. If it exists in the said range, since the blue photosensitive resin composition becomes highly sensitive and the intensity
- photoinitiator start adjuvant can be used.
- a photoinitiator adjuvant may be used in combination with a photoinitiator, and is a compound used in order to accelerate superposition
- photopolymerization start adjuvant an amine compound, an alkoxy anthracene type compound, a thioxanthone type compound, etc. are mentioned.
- Examples of the amine compound include triethanolamine, methyl diethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, and 2-dimethylamino benzoic acid.
- Ethyl, 2-ethylhexyl 4-dimethylaminobenzoic acid, N, N-dimethylparatoluidine, 4,4'-bis (dimethylamino) benzphenone (commonly known as Michler's ketone), 4,4'-bis (diethyl Amino) benzophenone, 4, 4'-bis (ethylmethylamino) benzophenone, etc. are mentioned, Among these, 4,4'-bis (diethylamino) benzophenone is preferable.
- an alkoxy anthracene type compound 9,10- dimethoxy anthracene, 2-ethyl-9,10- dimethoxy anthracene, 9,10- diethoxy anthracene, 2-ethyl-9, 10- diethoxy anthracene, for example.
- Etc. can be mentioned.
- a thioxanthone type compound 2-isopropyl thioxanthone, 4-isopropyl thioxanthone, 2, 4- diethyl thioxanthone, 2, 4- dichloro thioxanthone, 1-chloro- 4-propoxy city oxanthone etc. are mentioned.
- photoinitiators (D) may be used alone or in combination of a plurality thereof.
- a commercially available thing can be used as a photoinitiator starter,
- brand name "EAB-F” manufactured by Hodogaya Chemical Co., Ltd.
- EAB-F manufactured by Hodogaya Chemical Co., Ltd.
- the amount thereof is usually 10 mol or less, preferably 0.01 to 5 mol, per mol of the photopolymerization initiator.
- the sensitivity of a blue photosensitive resin composition becomes higher and the productivity of the color filter formed using this composition tends to improve, it is preferable.
- the solvent contained in the blue photosensitive resin composition of this invention is not specifically limited, Various organic solvents used in the field of a blue photosensitive resin composition can be used. Specific examples thereof include ethylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, and diethylene.
- ethylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, and diethylene.
- Diethylene glycol dialkyl ethers such as glycol dipropyl ether and diethylene glycol dibutyl ether, ethylene glycol alkyl ether acetates such as methyl cellosolve acetate and ethyl cellosolve acetate, propylene glycol monomethyl ether acetate, and propylene glycol Alkylene glycol alkyl ether acetates such as monoethyl ether acetate, propylene glycol monopropyl ether acetate, methoxybutyl acetate and methoxypentyl acetate, aromatic hydrocarbons such as benzene, toluene, xylene and mesitylene, methyl Ketones such as methyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone, cyclohexanone, ethanol, propanol, butanol, hexanol, cyclohexanol, alcohol
- organic solvents having a boiling point of 100 to 200 are preferable in the solvents in terms of applicability and dryness, and more preferably alkylene glycol alkyl ether acetates, ketones and ethyl 3-ethoxypropionate.
- esters such as methyl 3-methoxypropionate, and more preferably propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, ethyl 3-ethoxypropionate, and 3-methoxy Methyl propionate etc. are mentioned.
- These solvents can be used individually or in mixture of 2 or more types, respectively.
- Content of the solvent in the blue photosensitive resin composition of this invention can be contained 60-90 mass%, Preferably it is 60-85 mass% with respect to the whole blue photosensitive resin composition containing it.
- content of a solvent is the said range, since applicability
- the blue pattern layer blue photosensitive resin composition which concerns on this invention is a filler, another high molecular compound, a pigment dispersant as needed.
- Additives such as an adhesion promoter, antioxidant, a ultraviolet absorber, and an aggregation inhibitor, can be further included.
- the other polymer compound examples include curable resins such as epoxy resins and maleimide resins, thermoplastic resins such as polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ethers, polyfluoroalkyl acrylates, polyesters, polyurethanes, and the like. Can be.
- surfactants can be used as the pigment dispersant, and examples thereof include surfactants such as silicone, fluorine, ester, cationic, anionic, nonionic and amphoteric. These can be used individually or in combination of 2 types or more, respectively.
- polyoxyethylene alkyl ether For example, polyoxyethylene alkyl ether, polyoxyethylene alkyl peer ether, polyethyleneglycol diester, sorbitan fatty acid ester, fatty acid modified polyester, tertiary amine modified polyurethane , Polyethylenimine, etc.
- trade names include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), POLYFLOW (manufactured by Kyoeisha Chemical Co., Ltd.), EFTOP (manufactured by Tochem Products), MEGAFAC (manufactured by Dainippon Ink Chemical Industries, Ltd.), Florard (manufactured by Sumitomo 3M), Asahi guard, Surflon (above, manufactured by Asahi Glass), Sol SLSPERSE (made by Genka Corporation), EFKA (made by EFKA Chemicals), PB 821 (made by Ajinomoto Co., Ltd.), etc. are mentioned.
- adhesion promoter for example, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, 3-aminoprotriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2 -(3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercaptopropyl Trimethoxysilane etc. are mentioned. Specific examples of the antioxidant include 2,2'-
- ultraviolet absorber examples include 2- (3-tert-butyl-2-hydroxy-5-methylphenyl) -5-chlorobenzothiazole, alkoxybenzophenone and the like.
- aggregation inhibitor examples include sodium polyacrylate and the like.
- the additives can be used by those skilled in the art as appropriate without departing from the effect of the present invention.
- the additive may be used in an amount of 0.05 to 10 parts by weight, preferably 0.1 to 10 parts by weight, more preferably 0.1 to 5 parts by weight, based on 100 parts by weight of the total blue photosensitive resin composition, but is not limited thereto.
- the blue photosensitive resin composition which concerns on this invention can be manufactured, for example by the following method.
- the scattering particles are mixed with the solvent in advance and dispersed using a bead mill or the like until the average particle diameter becomes 30 to 500 nm.
- a dispersing agent can be further used as needed, and some or all of binder resin may be mix
- the remaining dispersion of the binder resin, the photopolymerizable compound, the photopolymerization initiator, other components used as necessary, and additional solvents as necessary, are further added to the obtained dispersion (hereinafter sometimes referred to as a mill base) to a predetermined concentration.
- a desired blue photosensitive resin composition can be obtained.
- Another aspect of the present invention relates to a color filter comprising a blue pattern layer containing a cured product of the blue photosensitive resin composition for forming a blue pattern layer described above.
- the color filter according to the present invention is made of the blue photosensitive resin composition for forming the blue pattern layer instead of the blue quantum dots, the manufacturing cost can be lowered and an excellent viewing angle can be obtained.
- the color filter including the blue pattern layer prepared using the blue photosensitive resin composition of the present invention controls the development speed
- the color filter includes a substrate and a blue pattern layer formed on the substrate.
- the substrate may be the substrate of the color filter itself, or may be a portion where the color filter is positioned in a display device or the like, and is not particularly limited.
- the substrate may be glass, silicon (Si), silicon oxide (SiOx), or a polymer substrate, and the polymer substrate may be polyethersulfone (PES) or polycarbonate (PC).
- the blue pattern layer is a layer including the blue photosensitive resin composition of the present invention, and may be a layer formed by applying the blue photosensitive resin composition for forming a blue pattern layer and exposing, developing and thermosetting in a predetermined pattern. Can be formed by carrying out methods commonly known in the art.
- the color filter may further include one or more selected from the group consisting of a red pattern layer and a green pattern layer.
- the red pattern layer or green pattern layer may include a quantum dot and / or scattering particles.
- the color filter according to the present invention may include a red pattern layer including a red quantum dot or a green pattern layer including a green quantum dot, and the red pattern layer or the green pattern layer may include scattering particles.
- the red pattern layer or the green pattern layer may emit red light or blue light, respectively, by a light source emitting blue light, which will be described later.
- the scattering particles included in the red pattern layer or the green pattern layer may include a metal oxide having an average particle diameter of 30 to 500nm, the details of the scattering particles and the metal oxide The content of the scattering particles and the metal oxide contained in the blue photosensitive resin composition according to the invention can be applied.
- the shape, configuration, and content of the quantum dots included in the red pattern layer or the green pattern layer are not limited, and quantum dots commonly used in the art may be applied.
- the color filter including the substrate and the pattern layer may further include a partition formed between each pattern, and may further include a black matrix, but is not limited thereto.
- the color filter may be a self-luminous color filter.
- the above-described color filter And a light source emitting blue light.
- the image display apparatus includes a color filter including a blue pattern layer including a cured product of the above-described blue photosensitive resin composition and a light source emitting blue light.
- the color filter of the present invention can be applied to various image display devices such as electroluminescent display devices, plasma display devices, field emission display devices, as well as ordinary liquid crystal display devices.
- the image display device includes a color filter including a blue pattern layer and the light source according to the present invention
- a color filter including a blue pattern layer and the light source according to the present invention there is an advantage of having excellent light emission intensity or viewing angle.
- the blue pattern layer included in the color filter according to the present invention does not include blue quantum dots, there is an advantage in that an image display device having low manufacturing cost can be manufactured.
- a flask equipped with a stirrer, a thermometer reflux condenser, a dropping lot, and a nitrogen inlet tube was prepared, and as the monomer dropping lot, 74.8 g (0.20 mol) of benzylmaleimide, 43.2 g (0.30 mol) of acrylic acid, and vinyltoluene 118.0 g (0.50 mol), 4 g of t-butylperoxy-2-ethylhexanoate and 40 g of propylene glycol monomethyl ether acetate (PGMEA) were added thereto, followed by stirring and mixing.
- PGMEA propylene glycol monomethyl ether acetate
- n-dodecanethiol 6g and PGMEA24g were added, and the thing mixed with stirring was prepared.
- the temperature was melt
- the temperature was heated to 120 ° C. to completely dissolve it.
- the acid value was measured and stirred until the acid value was less than 1.0 mgKOH / g. It took 11 hours to reach the target (0.8).
- the temperature of the reactor was lowered to room temperature to obtain a colorless transparent compound of formula 1-2-1.
- the temperature was melt
- the temperature was heated to 120 ° C. to completely dissolve it.
- the acid value was measured and stirred until the acid value was less than 1.0 mgKOH / g. It took 11 hours to reach the target (0.8).
- the temperature of the reactor was lowered to room temperature to obtain a colorless transparent compound of formula 1-2-2.
- HLC-8120GPC manufactured by Tosoh Corporation
- the ratio of the weight average molecular weight and number average molecular weight obtained above was made into molecular weight distribution (Mw / Mn).
- Color filters were prepared using the metal oxide photosensitive resin compositions prepared in Examples 1 to 9 and Comparative Examples 1 to 7. That is, each of the photosensitive resin composition was applied on a glass substrate by spin coating, and then placed on a heating plate and maintained at a temperature of 100 ° C. for 3 minutes to form a thin film.
- test photomask having a transmissive pattern of 20 mm x 20 mm square and a line / space pattern of 1 to 100 ⁇ m was placed on the thin film and irradiated with ultraviolet rays at a distance of 100 ⁇ m from the test photomask.
- the ultraviolet light source was irradiated with an exposure amount (365 nm) of 200 mJ / cm 2 under an atmospheric atmosphere using an ultra high pressure mercury lamp (trade name USH-250D) manufactured by Ushio Denki Co., Ltd., and no special optical filter was used.
- an ultra high pressure mercury lamp (trade name USH-250D) manufactured by Ushio Denki Co., Ltd., and no special optical filter was used.
- the thin film irradiated with ultraviolet rays was developed by soaking for 80 seconds in a KOH aqueous solution developing solution of pH 10.5.
- the thin film coated glass plate was washed with distilled water, dried by blowing nitrogen gas, and heated in a heating oven at 150 ° C. for 10 minutes to prepare a color filter pattern.
- the film thickness of the color pattern prepared above was 5.0 ⁇ m.
- the color filters prepared from the blue photosensitive resin compositions of Examples 1 to 5 and Comparative Examples 1 to 3 were evaluated as shown in Table 3 below. Evaluation criteria for each experiment are as follows.
- Sensitivity The degree of formation of a flawless thin film of the sensitivity mask fine pattern (1 to 60) (the lower the value, the better the sensitivity).
- Pattern Stability Pattern error after exposure of pattern mask at low exposure amount (20-100mJ)
- ⁇ , X is the result confirmed by the optical microscope of the three-dimensional surface shaper.
- Tapered line width ( ⁇ m) Post-exposure line width of 100 ⁇ m pattern of pattern mask.
- the developing speed exceeds 60 seconds, it is impossible to manufacture within a given process time, and if it exceeds 30 seconds, the roughness of the pattern surface becomes uneven and uniformity may also be reduced.
- the development speed was less than 30 seconds, and the sensitivity was less than 60, and it was confirmed that the pattern stability and the taper line width had excellent effects.
- Comparative Example 1 the scattering particles are not included, the pattern stability is unstable, causing an imbalance of the pattern.
- Comparative Example 2 when combined with only acrylic resin, the scattering particles and the blue colorant could not be supported as strongly as the cardo-based binder resin, and thus peeled off, and in Comparative Example 3, photopolymerizable without ethylene oxide and propylene oxide In the case of the compound, the development speed was significantly decreased, and the long development speed confirmed that pattern stability and pattern imbalance occurred.
- the size of the pattern obtained through the line / space pattern mask designed to 100 ⁇ m of the color filters manufactured using the metal oxide photosensitive resins prepared in Examples 1 to 5 and Comparative Examples 1 to 3 was obtained by OM equipment (ECLIPSE LV100POL Nikon). G) through the pattern size was measured, the results are shown in Table 4 below.
- the difference between the design value of the line / space pattern mask and the measured value of the obtained fine pattern is 20 ⁇ m or more, it is difficult to implement the fine pixel.
- Diffusion rate (B 70 + B 20 ) / 2 x B 5 x 100
- I means light intensity measured at each angle, and means measured at B 70, B 20, B 5 70 degrees, 20 degrees and 5 degrees.
- Examples 1 to 5 including the photopolymerizable compound added with ethylene oxide and propylene oxide had a diffusion ratio of 85 or more, and it was confirmed that the viewing angle was very excellent.
- Comparative Examples 1 and 3 the diffusion rate was remarkably dropped compared to Examples 1 to 5, and it was confirmed that the diffusion angle could not be measured because the viewing angle was lowered or peeled off.
- the present invention includes a photopolymerizable compound containing alkylene oxide in the blue photosensitive resin composition, to control the development speed, solve the problem caused by the process residue by eliminating the residue of the pattern, and poor display problems are improved
- the present invention provides a color filter in which the problem of resist non-developing is improved.
- it is possible to provide a high-quality self-luminous color filter having an excellent viewing angle by adjusting the taper.
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Abstract
La présente invention concerne une composition de résine photosensible bleue, un filtre coloré produit à l'aide de celle-ci, et un dispositif d'affichage d'image, la composition de résine photosensible bleue comprenant des particules de diffusion, une coloration bleue, une résine liante à base de cardo en tant que résine liante, un photo-initiateur, un composé photopolymérisable et un solvant, le composé photopolymérisable comprenant un composé photopolymérisable comportant un oxyde d'alkylène.
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CN201780088708.9A CN110446975A (zh) | 2017-03-31 | 2017-11-30 | 蓝色感光性树脂组合物、利用它制造的滤色器及图像显示装置 |
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