CN101329420A - Thermosetting resin composition for preparing color filter and color filter as well as sensor - Google Patents
Thermosetting resin composition for preparing color filter and color filter as well as sensor Download PDFInfo
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- CN101329420A CN101329420A CNA2008100848091A CN200810084809A CN101329420A CN 101329420 A CN101329420 A CN 101329420A CN A2008100848091 A CNA2008100848091 A CN A2008100848091A CN 200810084809 A CN200810084809 A CN 200810084809A CN 101329420 A CN101329420 A CN 101329420A
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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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L31/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid; Compositions of derivatives of such polymers
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- 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
- G03F7/20—Exposure; Apparatus 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
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
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Abstract
A thermosetting resin composition for producing a color filter for a CMOS image sensor is provided. The thermosetting resin composition comprises an organic solvent and a self-curing copolymer having structural units represented by Formulae 1, 2, 3 and 4, which are described in the specification.
Description
The cross reference of related application
This non-provisional application requires the right of priority of the korean patent application No.10-2007-0059842 of submission on June 19th, 2007, and this application is incorporated herein by reference in full at this.
Technical field
The present invention relates to a kind of compositions of thermosetting resin of CMOS (complementary metal oxide semiconductor (CMOS)) imageing sensor that be used to prepare, comprise the color filter of the hyaline membrane that uses said composition formation, and use the cmos image sensor of this color filter with color filter.
Background technology
The color filter that is used for imageing sensor can comprise and is formed on the color filter surface or subsurface hyaline membrane, to improve flatness and protection color filter.Described hyaline membrane must be optical clear at visible area, must have high film strength and present subsequent technique such as heating, cleaning, development and etched thermotolerance and the chemical resistance that is enough to bear after forming hyaline membrane.Especially, presentation manager should be able to suppress the ultraviolet reflection of irradiation with patterning chromatic photoresist (color resist) with the bottom hyaline membrane of color filter, and therefore prevents to produce pattern defect by various negative factors such as halation (halation) and standing wave on color filter.
Japanese kokai publication hei 1-134306, spy open clear 62-163016 and the clear 63-131103 of Te Kai discloses the composition that is used for color filter usefulness hyaline membrane, and said composition contains glycidyl methacrylate, polyimide, reaches the potpourri of melamine resin and epoxy resin respectively as principal ingredient.
Composition epoxy resin can be used to prepare the color filter diaphragm with reliable bond strength, thermotolerance, chemical resistance and water tolerance.For example, Japanese kokai publication hei 08-050289 discloses a kind of curable resin composition that contains glycidyl methacrylate polymkeric substance and phenol hardening agent (phenolic curing agent).And Japanese kokai publication hei 08-201617 discloses a kind of resin combination that contains epoxy resin, hardening agent and organic solvent that is used for hyaline membrane, and wherein, described hardening agent is the reaction product of styrene-maleic anhydride copolymer and amine.
Usually since with the rapid reaction of hardening agent, epoxy resin is mixing before being about to use with hardening agent (being called as " two-component composition ").Known, epoxy resin also is not suitable for the preparation single-component composition.But two-component composition is handled complicated, is not suitable for the industrial scale preparation.
The all unexposed single-component composition that contains epoxy resin and satisfy transparency, film strength, thermotolerance, acid resistance and alkali-proof requirement simultaneously of above-mentioned art methods.And, the also untapped color filter hyaline membrane that goes out can absorb ultraviolet light.
Summary of the invention
According to an aspect of the present invention, provide a kind of compositions of thermosetting resin that is used to prepare color filter.Compositions of thermosetting resin of the present invention has excellent adhesion strength, transparency, film strength, thermotolerance, acid resistance, alkali resistance and long term storage stability and can absorb the ultraviolet light of specific wavelength.
Compositions of thermosetting resin of the present invention contains organic solvent and contains the self-curing multipolymer of the structural unit shown in formula 1, formula 2, formula 3 and the formula 4:
Wherein, R
1Be hydrogen atom or methyl, n is 1 to 10 integer;
Wherein, R
2Be hydrogen atom or methyl, m is 1 to 10 integer;
Wherein, R
3Be hydrogen atom or methyl; With
Wherein, R
4Be hydrogen atom or methyl, Z is selected from following group:
Described self-curing multipolymer can contain the structural unit of the formula 1 of the 5-90mol% that has an appointment, the structural unit of the formula 2 of about 1-30mol%, the structural unit of the formula 3 of about 1-30mol%, and the structural unit of the formula 4 of about 0.5-20mol%.
Described self-curing multipolymer can also contain the structural unit of 6 formulas of formula:
Wherein, X is selected from
O is 1 to 4 integer, and p is 4 to 12 integer, and Y is selected from hydrogen atom, C
1-C
4Low alkyl group and C
1-C
4Lower alkoxy.
The structural unit of formula 6 can exist with the amount of about 0.5-20mol%.
Described self-curing multipolymer can have the weight-average molecular weight of about 1000-1000000.
Compositions of thermosetting resin of the present invention can also contain epoxy compound.
Compositions of thermosetting resin of the present invention can contain the self-curing multipolymer of the 1-45 weight % that has an appointment, the epoxy compound of about 1-45 weight % and the organic solvent of surplus.
Described epoxy compound can be selected from the group of being made up of the epoxy compound of bisphenol type epoxy compound, Bisphenol F type epoxy compound, novolac-type epoxy compound, cresols line style phenolic epoxy compound and replacement.These epoxy compounds can use separately or use with their form of mixtures.
Described self-curing multipolymer can also contain at least a in the group of being made up of following structural unit: (methyl) esters of acrylic acid comprises (methyl) methyl acrylate, (methyl) ethyl acrylate, (methyl) propyl acrylate, (methyl) isopropyl acrylate, (methyl) butyl acrylate and (methyl) acrylic acid benzene methyl; Acrylic amide, comprise N methacrylamide, N-ethyl acrylamide, N-N-isopropylacrylamide, N hydroxymethyl acrylamide, N-methyl acrylamide, N-ethyl-methyl acrylamide, N-isopropyl methyl acrylamide, N-methylol methacrylamide, N, N-DMAA, N, N-diethyl acrylamide, N, N-dimethylmethacryl amide and N, N-diethylmethyl acrylamide; Phenylethylene comprises styrene, α-Jia Jibenyixi, reaches hydroxy styrenes; The N-vinyl pyrrolidone; The N-vinyl formamide; The N-vinylamide; And N-vinyl imidazole.
Composition of the present invention can also contain at least a polymkeric substance that is selected from polymethacrylate, nylon, polyester, polyimide and polysiloxane (polysilicon).With the described self-curing multipolymer of 100 weight portions is benchmark, and the amount of described polymkeric substance is about 50 weight portions or still less.
According to another aspect of the present invention, provide a kind of color filter that comprises the hyaline membrane that uses described composition formation.
According to a further aspect of the invention, also provide a kind of imageing sensor that uses described color filter.
Description of drawings
Fig. 1 is the synoptic diagram of the structure of explanation cmos image sensor.
Fig. 2 produces the synoptic diagram of the mechanism of pattern defect owing to the light reflection for explanation.
Fig. 3 has shown by the chromatic photoresist that will be used for cmos image sensor and is applied to hyaline membrane that Comparative Examples 1 forms, makes the chromatic photoresist exposure and the shape of the resulting pattern of chromatic photoresist that exposed of developing.
Fig. 4 has shown by the chromatic photoresist that will be used for cmos image sensor and is applied to hyaline membrane that embodiment 1 forms, makes the chromatic photoresist exposure and the shape of the resulting pattern of chromatic photoresist that exposed of developing.
Embodiment
To describe the present invention in more detail hereinafter, wherein, describe part of the present invention but non-whole embodiment.In fact, can realize the present invention, and should not be construed as and be limited to given embodiment herein by many different modes; On the contrary, providing these embodiments is in order to make the disclosure satisfy the legal provisions that are suitable for.
The invention provides a kind of compositions of thermosetting resin of cmos image sensor that can be used for preparing with color filter.Particularly, compositions of thermosetting resin of the present invention contain organic solvent and have the UVA group from the solidity multipolymer.
Described have by the structural unit shown in formula 1, formula 2, formula 3 and the formula 4 from the solidity multipolymer:
Wherein, R
1Be hydrogen atom or methyl, n is 1 to 10 integer;
Wherein, R
2Be hydrogen atom or methyl, m is 1 to 10 integer;
Wherein, R
3Be hydrogen atom or methyl; With
Wherein, R
4Be hydrogen atom or methyl, Z is selected from following group:
Because the structural unit of formula 1 and the structural unit heat cross-linking of formula 2, formula 3 and formula 4, therefore described self-curing multipolymer has the thermosetting performance.Have formula 1 to the self-curing multipolymer of the structural unit of formula 4 and can be any kind such as random copolymers, alternating copolymer, segmented copolymer or graft copolymer.
The self-curing multipolymer can contain the structural unit of the formula 1 of the 5-90mol% that has an appointment, the structural unit of the formula 2 of about 1-30mol%, the structural unit of the formula 3 of about 1-30mol%, and the structural unit of the formula 4 of about 0.5-20mol%.
Especially, the structural unit of formula 4 has UVA group (Z).The existence of group (Z) has stoped because the generation of the pattern defect due to the various negative factors.For example, with reference to mechanism shown in Figure 2, when chromatic photoresist was exposed, the unexposed portion of chromatic photoresist was not reflected by the ultraviolet light of following substrate again and solidifies.
Described self-curing multipolymer can also optionally contain the structural unit of formula 6, and its existence can improve the bin stability and the film hardness of described composition:
Wherein, wherein, X is selected from
O is 1 to 4 integer, and p is 4 to 12 integer, and Y is selected from hydrogen atom, C
1-C
4Low alkyl group and C
1-C
4Lower alkoxy.
The amount of the structural unit of formula 6 can be about 0.5-20mol%.
The weight-average molecular weight of described self-curing multipolymer can be about 1000 to about 1000000.When the weight-average molecular weight of described self-curing multipolymer less than about 1000 the time, the self-curing multipolymer can fully not solidify.Simultaneously, when the weight-average molecular weight of self-curing multipolymer greater than about 1000000 the time, described multipolymer can have the solubleness that reduces or be difficult to described composition is coated on the substrate.General assembly (TW) with composition is a benchmark, and the amount that described self-curing multipolymer is present in the compositions of thermosetting resin is about 1-45 weight %.
The kind that is used for the organic solvent of composition of the present invention is not particularly limited.Being used for representative examples of organic of the present invention includes but not limited to: glycols comprises ethylene glycol and diethylene glycol; Glycol ethers comprises glycol monoethyl ether, diethylene glycol monomethyl ether, ethylene glycol diethyl ether, reaches diethylene glycol dimethyl ether; The glycol ethers acetate esters comprises ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetic acid esters and butyl carbitol acetate; Propandiols; The propylene glycol ethers comprises propylene glycol monomethyl ether, dihydroxypropane single-ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, Propylene Glycol Dimethyl Ether, dipropylene glycol dimethyl ether, propylene glycol diethyl ether and dipropylene glycol diethyl ether; The propylene glycol acetate esters comprises propylene glycol methyl ether acetate and dipropylene glycol monoethyl ether acetate; Amide-type comprises N-Methyl pyrrolidone, dimethyl formamide and dimethyl acetamide; Ketone comprises methyl ethyl ketone (MEK), methyl isobutyl ketone (MIBK) and cyclohexanone; The white spirit class comprises toluene, dimethylbenzene and solvent naphtha; The ester class comprises ethyl acetate, butyl acetate and ethyl lactate; And their potpourri.
Remove the content of self-curing multipolymer and other composition, organic solvent has been supplied remaining percentage by weight in the composition.General assembly (TW) with composition is a benchmark, and composition of the present invention can contain have an appointment 30-99 weight %, the organic solvent of 70-98 weight % according to appointment.If composition contains the organic solvent less than about 30 weight %, then be difficult to described composition is coated on the substrate.Simultaneously, if described composition contains the organic solvent greater than about 99 weight %, then be difficult to form enough thick diaphragm.
For improving elching resistant and alkali resistance and adjusting flowability, the present composition also optionally contains epoxy compound.Described epoxy compound can be for being selected from the epoxy compound in the group that epoxy compound by bisphenol type epoxy compound, Bisphenol F type epoxy compound, novolac-type epoxy compound, cresols novolac-type epoxy compound and replacement etc. forms.These epoxy compounds can use separately or use with their form of mixtures.The weight-average molecular weight of described epoxy compound can be about 50-10000.General assembly (TW) with composition is a benchmark, and the content of the epoxy compound in the compositions of thermosetting resin can be about 1-45 weight %, 5-30 weight % according to appointment.The amount of epoxy compound is during less than about 1 weight %, can cause using the dimensional stability of the hyaline membrane that described composition forms to reduce.Simultaneously, the amount of epoxy compound can be difficult to described composition is coated on the substrate during greater than about 45 weight %.
For improving or giving the present composition other performance, as ease for use, film hardness with to the affinity of last film with following film, described self-curing multipolymer also optionally contains and is selected from least a in the group of being made up of following repetitive: (methyl) esters of acrylic acid comprises (methyl) methyl acrylate, (methyl) ethyl acrylate, (methyl) propyl acrylate, (methyl) isopropyl acrylate, (methyl) butyl acrylate and (methyl) acrylic acid benzene methyl; Acrylic amide, comprise N methacrylamide, N-ethyl acrylamide, N-N-isopropylacrylamide, N hydroxymethyl acrylamide, N-methyl acrylamide, N-ethyl-methyl acrylamide, N-isopropyl methyl acrylamide, N-methylol methacrylamide, N, N-DMAA, N, N-diethyl acrylamide, N, N-dimethylmethacryl amide and N, N-diethylmethyl acrylamide; Phenylethylene comprises styrene, α-Jia Jibenyixi, reaches hydroxy styrenes; The N-vinyl pyrrolidone; The N-vinyl formamide; The N-vinylamide; With the N-vinyl imidazole etc., and their potpourri.
Can use any suitable method known in the art to synthesize the self-curing multipolymer.As nonrestrictive example, can with the used identical organic solvent of compositions of thermosetting resin of the present invention in use radical polymerization initiator to synthesize described self-curing multipolymer.
Be used for synthetic described organic solvent and be not particularly limited with self-curing multipolymer of ultraviolet absorption group, and can be identical with the used solvent of compositions of thermosetting resin of the present invention.On the other hand, can control the amount of the used organic solvent of polyreaction, feasible weight with the solution of self-curing multipolymer in organic solvent is benchmark, and the amount that described self-curing multipolymer exists is about 3-50 weight %, according to appointment 5-30 weight %.When the concentration of self-curing multipolymer in the solution during less than about 3 weight %, polymerization rate can reduce, and therefore some monomers can be residual and unreacted.Simultaneously, when the concentration of self-curing multipolymer in the solution surpassed 50 weight %, solution can be too sticking and can't handle and can not control reaction rate.
Can use any known polymerization initiator to synthesize described self-curing multipolymer, this initiating agent comprises: thermal polymerization, Photoepolymerizationinitiater initiater, and redox initiator.Because be easy to handle and be easy to control reaction rate and molecular weight, the present invention can use peroxide type and azo-type radical polymerization initiator.
The example that can be used for peroxide type polymerization initiator of the present invention comprises: methyl ethyl ketone peroxide; cyclohexanone peroxide; the peroxidating methyl cyclohexanone; the acetyl peroxide benzylacetone; 1; 1-bis(t-butylperoxy)-3; 3; the 5-trimethyl-cyclohexane; 1; the 1-bis(t-butylperoxy) cyclohexane; 1; two (the uncle's hexyl peroxies)-3 of 1-; 3; the 5-trimethyl-cyclohexane; 1; two (the uncle's hexyl peroxy) cyclohexanes of 1-; 1; 1-bis(t-butylperoxy) cyclododecane; isobutyl peroxide (isobutyl peroxide); lauroyl peroxide; succinic acid peroxide; peroxidating 3; 3; the 5-trimethyl acetyl; benzoyl peroxide; the peroxidating decoyl; stearoyl; di-isopropyl peroxydicarbonate; the peroxy dicarbonate di-n-propyl ester; di; di; two (the 2-methoxyl butyl) esters of peroxide two carbonic acid; two (4-tert-butylcyclohexyl) esters of peroxide two carbonic acid; (α; α-two new caprinoyl peroxies) diisopropyl benzene ((α; the diisopropylbenzene of α-bis-neodecanoylperoxy)); peroxidating neodecanoic acid isopropyl benzene ester; peroxidating neodecanoic acid monooctyl ester; the own ester of peroxidating neodecanoic acid; new peroxide tert-butyl caprate; the own ester of peroxidating neopentanoic acid uncle; the peroxidating neopentanoic acid tert-butyl ester; 2; 5-dimethyl-2; two (peroxidating of the 2-ethyl hexanoyl base) hexanes of 5-; 1; 1; 3; 3-tetramethyl butyl peroxidating-2 ethyl hexanoic acid ester; peroxidating-2-ethyl-uncle's hexyl capronate; peroxidating-2-ethyl-tert-butyl group capronate; peroxidating-2-ethyl-tert-butyl group capronate; peroxidating-3-methyl-tert-butyl group propionic ester; the peroxidating lauric acid tert-butyl ester; tert-butyl hydroperoxide-3; 5; 5-tri-methyl hexanoic acid ester; uncle's hexyl peroxy isopropyl base one carbonic ester; BPIC (t butyl peroxy isopropyl carbonate); 2; 5-dimethyl-2; 5-two (benzoyl peroxide) hexane; t-butyl peroxy-acetate; the own ester of benzylhydroperoxide uncle; t-butyl perbenzoate etc., and their potpourri.The combination of peroxide type polymerization initiator and reductive agent can be used as redox initiator and uses.
The example that can be used for azo-type polymerization initiator of the present invention comprises: 1,1-azo two (cyclohexane-1-nitrile), 2,2 '-azo two (2-methylbutyronitrile), 2,2 '-azo dibutyronitrile, 2,2 '-azo two (2, the 4-methyl pentane nitrile), 2,2 '-azo two (2,4-dimethyl-4-methoxyl valeronitrile), 2,2 '-azo two (2-amidine propane) hydrochloride, 2,2 '-azo two [2-(5-methyl-2-imidazoline-2-yl) propane] hydrochloride, 2,2 '-azo two [2-(2-imidazoline-2-yl) propane] hydrochloride, 2,2 '-azo two [2-(5-methyl-2-imidazoline-2-yl) propane], 2,2 '-azo two [2-methyl-N-(1, two (2-the methylol)-2-hydroxyethyls of 1-) propionamide, 2,2 '-azo two [2-methyl-N-(2-hydroxyethyl) propionamide], 2,2 '-azo two (2-methyl-propionamide) dihydrate, 4,4 '-azo two (4-cyanopentanoic acid), 2,2 '-azo two (2-methylol propionitrile), 2,2 '-azo two (2 Methylpropionic acid) dimethyl ester (dimethyl-2,2 '-azo two (2 Methylpropionic acid ester)), cyano group-2-propyl group azodicarbonamide etc., and their potpourri.
Except that these peroxide type and azo-type polymerization initiator, in the building-up process of self-curing multipolymer, also can add at least a known molecular weight regulator such as chain-transferring agent, chain terminating agent or polymerization accelerant, so that the molecular weight of described self-curing multipolymer is adjusted to scope as defined above.Suitable molecular weight regulator can be to dredge basic propionic acid, thin basic propionic ester, sulphur glycol (thioglycol), thioglycerin, lauryl mercaptan, α-Jia Jibenyixierjuwu etc., and their potpourri.
Except being used to prepare the organic solvent of multipolymer, can add one or more solvents to reach dissolving of after polymerization, assisting constituent and the purpose of controlling levelability and rate of drying.
In addition, described multipolymer can by unconfined known technology such as spray drying, film drying, splash in the poor solvent and again dipping be extracted into solid-state form and change for purifying, storage and solvent.
In order to improve elching resistant and alkali resistance, and influence liquidity, with the described self-curing multipolymer of 100 weight portions is benchmark, and composition of the present invention can also contain at least a polymkeric substance in have an appointment 50 weight portions or still less poly-(methyl) acrylate, nylon, polyester, polyimide or the polysiloxane.
Can also add thermal curing catalyst in the compositions of thermosetting resin of the present invention.The example that can be used for thermal curing catalyst of the present invention comprises: amines, phosphorus compound, boron compound, antimonial, carboxylic acid compound, organic sulfonic acid compound etc., and their potpourri.For obtaining good storage-stable, be benchmark with the described self-curing polymer of 100 weight portions, the addition of described thermal curing catalyst can be for about 10 weight portions or still less.
As needs, compositions of thermosetting resin of the present invention can also oneself be known the reagent blend with other, as antioxidant, ultra-violet stabilizer, plastifier, levelling agent, filler etc., and their potpourri.
Use known technology,, compositions of thermosetting resin of the present invention can be coated on the substrate to form film as serigraphy, curtain coating, blade coating, spin coating, spraying, dip-coating, flow coat (flow coating), roller coating or slot coated.After follow-up drying, the film of Xing Chenging can have about 0.1-3.0 μ m, the thickness of 0.2-1.5 μ m according to appointment like this.If the thickness of described film can't reach the enough flatnesses with respect to ladder height (step height) less than about 0.1 μ m.Simultaneously, if the thickness of film greater than about 3.0 μ m, its transmittance can reduce, and also needs quite long drying and set time, and has reduced yield-power.
Can be dry and the substrate that applies with compositions of thermosetting resin of the present invention of heat curing with evaporating solvent, and solidify to form sufficiently rigid film by crosslinked.Drying and heat curing operation can be carried out at the same time or separately.Preferably carry out drying and heat curing operation respectively, this is because Fast Heating can cause forming foam and crackle in film.
The example that can be used for the equipment of described drying process includes, but not limited to hot-air drier, far-infrared dryer and electric hot plate.Described drying process can carry out in about 50-150 ℃ temperature range.Can change drying time according to capacity, air-flow, temperature and the film thickness of used exsiccator.Be about 1-10 minute exemplary drying time.
The example that is used for the equipment of described heat curing operation includes, but not limited to hot-air oven, far infrared baking oven and electric hot plate.Described heat curing operation can be carried out in about 150-250 ℃ temperature range.Can not meet the requirements about curing below 150 ℃.Simultaneously, more than 250 ℃ depolymerizing and carbonization of polymkeric substance can be taken place about, and can destroy the performance of telolemma.
The film that forms with compositions of thermosetting resin of the present invention can be applied to the color filter that imageing sensor is used.
Further describe the present invention below with reference to embodiment and Comparative Examples.But these embodiment only are used for illustrative purposes and are not limited to the present invention.
Embodiment
Embodiment 1
After in the flask of the 1000ml that is equipped with reflux condenser and stirrer, adding the 600g propylene glycol methyl ether acetate, under agitation temperature is increased to 80 ℃.Under agitation with 1.5-2 hour dropping 25g glycidyl methacrylate, 13g methacrylic acid-2-hydroxy methacrylate, 15g methacrylic acid, 9g methacrylic acid-9-anthracene methyl ester, 4g N-phenylmaleimide, 9g styrene, 100g methyl methacrylate and 20g dimethyl-2 in flask, the potpourri of 2 '-azo two (2 Methylpropionic acid ester), and keep 80 ℃ temperature.The gained potpourri was under agitation reacted 3-4 hour, and keeping temperature of reaction simultaneously is 80 ℃ of solution (a) with the random copolymers that obtains containing formula 7.
Using gel permeation chromatography (GPC), is standard with the polystyrene, and the weight-average molecular weight that records resulting polymers solution is 14500.
In 20g resulting polymers solution (a), add 1g epoxy resin (jER-152, JER), the 0.05g surfactant (R-08, DIC) and the 50g propylene glycol methyl ether acetate.Dissolving gained potpourri under fully stirring, and filtration obtains compositions of thermosetting resin (e).
Use spin coater with compositions of thermosetting resin (e) be coated on the thick glass substrate of 0.7mm (#1737, Corning) on, with exsiccator 80 ℃ dry 3 minutes down, and solidify 30 minutes down to prepare the thick hyaline membrane of 0.5 μ m at 230 ℃.
Embodiment 2
After in the flask of the 1000ml that is equipped with reflux condenser and stirrer, adding the 600g propylene glycol methyl ether acetate, under agitation temperature is increased to 80 ℃.Under agitation with 1.5-2 hour dropping 30g glycidyl methacrylate, 10g methacrylic acid-2-hydroxy methacrylate, 15g methacrylic acid, 5g 2-hydroxy-4-methyl acryloxy benzophenone, 5g N-phenylmaleimide, 10g styrene, 50g methyl methacrylate and 8g dimethyl-2 in flask, the potpourri of 2 '-azo two (2 Methylpropionic acid ester), and keep 80 ℃ temperature.The gained potpourri was under agitation reacted 4-5 hour, and keeping temperature of reaction simultaneously is 80 ℃ of solution (b) with the random copolymers that obtains containing formula 8.
Using gel permeation chromatography (GPC), is standard with the polystyrene, and the weight-average molecular weight that records resulting polymers solution is 11000.
Except that using 40g polymer solution (b) to replace the polymer solution (a), prepare compositions of thermosetting resin (f) by the method identical with embodiment 1.
Except that using compositions of thermosetting resin (f) to replace the compositions of thermosetting resin (e), the step of describing by embodiment 1 prepares the thick hyaline membrane of 0.5 μ m.
Embodiment 3
After in the flask of the 1000ml that is equipped with reflux condenser and stirrer, adding the 600g propylene glycol methyl ether acetate, under agitation temperature is increased to 80 ℃.Under agitation with 1.5-2 hour dropping 30g glycidyl methacrylate, 10g methacrylic acid-2-hydroxy methacrylate, 15g methacrylic acid, 100g methyl methacrylate, 10g 2-(2 '-hydroxyl-5 '-methacryloxy phenyl) benzotriazole, 15g N-phenylmaleimide, 33g styrene and 8g dimethyl-2 in flask, the potpourri of 2 '-azo two (2 Methylpropionic acid ester) keeps 80 ℃ temperature simultaneously.The gained potpourri was under agitation reacted 4-5 hour, and keeping temperature of reaction simultaneously is 80 ℃ of solution (c) with the random copolymers that obtains containing formula 9.
Using gel permeation chromatography (GPC), is standard with the polystyrene, and the weight-average molecular weight that records resulting polymers solution is 9500.
Except that using 40g polymer solution (c) to replace the polymer solution (a), prepare compositions of thermosetting resin (g) by the method identical with embodiment 1.
Except that using compositions of thermosetting resin (g) to replace the compositions of thermosetting resin (e), the step of describing by embodiment 1 prepares the thick hyaline membrane of 0.5 μ m.
Comparative Examples 1
After in the flask of the 1000ml that is equipped with reflux condenser and stirrer, adding the 600g propylene glycol methyl ether acetate, under agitation temperature is increased to 80 ℃.Under agitation with 1.5-2 hour dropping 30g glycidyl methacrylate in flask, 13g methacrylic acid two ring pentyl esters, 12g styrene, 25g methyl methacrylate and 10g dimethyl-2, the potpourri of 2 '-azo two (2 Methylpropionic acid ester), and keep 80 ℃ temperature.The gained potpourri was under agitation reacted 4-5 hour, and keeping temperature of reaction simultaneously is 80 ℃ of solution (d) with the random copolymers that obtains containing formula 10.
Using gel permeation chromatography (GPC), is standard with the polystyrene, and the weight-average molecular weight that records resulting polymers solution is 13000.
Except that using 40g polymer solution (d) to replace the polymer solution (a), prepare compositions of thermosetting resin (h) by the method identical with embodiment 1.
Except that using compositions of thermosetting resin (h) to replace the compositions of thermosetting resin (e), the step of describing by embodiment 1 prepares the thick hyaline membrane of 0.5 μ m.
Physical property evaluation
Estimate flatness, tack, film hardness and the transmittance of the prepared hyaline membrane of embodiment 1-3 and Comparative Examples 1 according to following each step.Chromatic photoresist is applied to each hyaline membrane, forms pattern then.Calculate because the number of the pattern defect that various negative factors such as halation cause.The gained result is as shown in table 1.
1. flatness evaluation
Difference in height (that is ladder height between pigment, between the center section of the red green pixel of measurement sample color filter.After each hyaline membrane with embodiment 1-3 and Comparative Examples 1 preparation is applied to the sample color filter, measure the ladder height between the color filter pixel.Ratio R by the ladder height (d2) behind ladder height (d1) before following equation (1) the computing application hyaline membrane and the application hyaline membrane:
R＝d2/d1.....(1)
According to following standard, the smooth performance of the compositions of thermosetting resin of embodiment 1-3 and Comparative Examples 1 preparation is divided into 5 grades: R＞0.4 ... 1 grade; 0.4≤R≤0.3 ... 2 grades; 0.3＜R≤0.2 ... 3 grades; 0.2＜R≤0.1 ... 4 grades; R＜0.1 ... 5 grades.
Progression is high more, and smooth performance is good more.
2. tack and chemical resistance test
After engraving stroke lattice of 100 cruciform stripeds on each hyaline membrane of embodiment 1-3 and Comparative Examples 1 preparation, peel off test (grid test) with cellophane tape.The state of peeling off of drawing lattice by visual detection is to estimate the tack of hyaline membrane.When stroke lattice are not stripped from, judge that tack is " qualified ".When one or more strokes of lattice are stripped from, judge that tack is " defective ".
In addition, under 40 ℃, respectively transparent membrane be impregnated in N-N-methyl-2-2-pyrrolidone N-(NMP) as organic solvent, 10% potassium hydroxide alkalescence aqueous solution and acid etching agent solution (LCE-12K, CYANTEK CORPORATION) in 30 minutes, repeats above-mentioned tack testing procedure to estimate chemical resistance.Observe the state of peeling off of drawing lattice.When after flooding each time, do not draw lattice and be stripped from, judge that chemical resistance is " qualified ".When after flooding each time, when one or more strokes of lattice are stripped from, judge that chemical resistance is " defective ".
3. film hardness evaluation
After using the hyaline membrane of 6 kinds of (1H-6H) pencils (Statdler) scraping embodiment 1-3 and Comparative Examples 1 preparation, observe the damage of film.According to damaged condition film strength is divided into 6 grades (1H-6H).
4. pattern defect evaluation (passing through halation)
Cmos image sensor is applied to each hyaline membrane that embodiment 1-3 and Comparative Examples 1 forms with color filter,, and develops to form pattern with rayed.Observe the shape of pattern.Calculating protrudes from the defective number of pattern edge.Pattern defect is because following substrate light reflection ultraviolet causes, as shown in Figure 2.With the shape of the transparent film formed pattern of Comparative Examples 1 and embodiment 1 preparation respectively shown in Fig. 3 and 4.
Table 1
From the result of table 1 as can be seen, the hyaline membrane that uses the compositions of thermosetting resin of logical embodiment 1-3 preparation to make demonstrates in the transmittance of flatness, tack, visible area and the excellent specific property on the film hardness.For example, film is transparent for the irradiation tunnel in the visible region basically, and for example presents that the minimum transmittance of 400nm wavelength radiation of visible light is at least about 98%.In addition, the hyaline membrane of absorption 365nm ultraviolet light helps the remarkable minimizing of pattern defect quantity.For example, film of the present invention can present the 365nm wavelength illumination max transmissive than being about 92%.
From above-mentioned obviously as can be known, compositions of thermosetting resin of the present invention is easy to handle and presents the better chemical resistance of bi-component thermoset resin that is used to prepare color filter than routine.In addition, use the color filter of compositions of thermosetting resin preparation of the present invention to demonstrate excellent flatness, tack, transmittance, film strength and thermotolerance with hyaline membrane.And compositions of thermosetting resin of the present invention has the ability that absorbs ultraviolet light.Therefore, when compositions of thermosetting resin of the present invention is used to prepare imageing sensor and uses color filter, by halation and again the number of the pattern defect that causes of the standing wave of light reflection ultraviolet can reduce.
For a person skilled in the art, benefit from the instruction that presents in the above description of the present invention and can associate a lot of modification of the present invention and other embodiment.Therefore, be appreciated that the present invention is not limited to disclosed specific embodiment, and it is revised and other embodiment should comprise within the scope of the appended claims.Though used particular term in this article, these terms only use with general descriptive meaning, rather than in order to limit the present invention, scope of the present invention is limited in claims.
Claims (20)
1. one kind prepares the compositions of thermosetting resin that color filter is used, and said composition contains organic solvent and contains the self-curing multipolymer of the structural unit of formula 1, formula 2, formula 3 and 4 formulas of formula:
In the formula 1, R
1Be hydrogen atom or methyl, and n is 1 to 10 integer;
In the formula 2, R
2Be hydrogen atom or methyl, and m is 1 to 10 integer;
In the formula 3, R
3Be hydrogen atom or methyl; With
In the formula 4, R
4Be hydrogen atom or methyl, and Z is selected from following group:
2. compositions of thermosetting resin according to claim 1, wherein, described self-curing multipolymer contains the structural unit of the 5-90mol% formula 1 of having an appointment, the structural unit of about 1-30mol% formula 2, the structural unit of the structural unit of about 1-30mol% formula 3 and about 0.5-20mol% formula 4.
3. compositions of thermosetting resin according to claim 1, wherein, described self-curing multipolymer also contains the structural unit of formula 6:
Wherein, X is selected from
O is 1 to 4 integer, and p is 4 to 12 integer, and Y is selected from hydrogen atom, C
1-C
4Low alkyl group and C
1-C
4In the lower alkoxy.
4. compositions of thermosetting resin according to claim 3, wherein, described self-curing multipolymer contains the structural unit of the 0.5-20mol% formula 6 of having an appointment.
5. compositions of thermosetting resin according to claim 1, wherein, the weight-average molecular weight of described self-curing multipolymer is about 1000-1000000.
6. compositions of thermosetting resin according to claim 1, wherein, described composition also contains epoxy compound.
7. compositions of thermosetting resin according to claim 6, wherein, described compositions of thermosetting resin contains the self-curing multipolymer of the 1-45 weight % that has an appointment, the epoxy compound of about 1-45 weight % and the organic solvent of surplus.
8. compositions of thermosetting resin according to claim 6, wherein, described epoxy compound be selected from by the epoxy compound of bisphenol type epoxy compound, Bisphenol F type epoxy compound, novolac-type epoxy compound, cresols line style phenolic epoxy compound, replacement, and the group formed of their potpourri in.
9. compositions of thermosetting resin according to claim 1, wherein, described self-curing multipolymer also contains at least a structural unit that is selected from the group of being made up of (methyl) acrylate, acrylamide, styrene, N-vinyl pyrrolidone, N-vinyl formamide, N-vinylamide and N-vinyl imidazole.
10. compositions of thermosetting resin according to claim 9, wherein, described (methyl) acrylate is selected from the group of being made up of (methyl) methyl acrylate, (methyl) ethyl acrylate, (methyl) propyl acrylate, (methyl) isopropyl acrylate, (methyl) butyl acrylate and methacrylic acid benzene methyl; Described acrylamide is selected from by N methacrylamide, N-ethyl acrylamide, N-N-isopropylacrylamide, N hydroxymethyl acrylamide, N-methyl acrylamide, N-ethyl-methyl acrylamide, N-isopropyl methyl acrylamide, N-methylol methacrylamide, N, N-DMAA, N, N-diethyl acrylamide, N, N-dimethylmethacryl amide and N are in the group that N-diethylmethyl acrylamide is formed; And described styrene is selected from the group of being made up of styrene, α-Jia Jibenyixi and hydroxy styrenes.
11. compositions of thermosetting resin according to claim 1, wherein, said composition also contains at least a polymkeric substance that is selected from poly-(methyl) acrylate, nylon, polyester, polyimide, polysiloxane and their potpourri.
12. compositions of thermosetting resin according to claim 1, wherein, described self-curing multipolymer comprise select the multipolymer shown in free style 7, formula 8 and the formula 9, and the group formed of their potpourri in multipolymer:
13. the film of a substantially transparent, described film derive from the self-curing multipolymer that contains the structural unit shown in formula 1, formula 2, formula 3 and the formula 4:
In the formula 1, R
1Be hydrogen atom or methyl, and n is 1 to 10 integer;
In the formula 2, R
2Be hydrogen atom or methyl, and m is 1 to 10 integer;
In the formula 3, R
3Be hydrogen atom or methyl; With
In the formula 4, R
4Be hydrogen atom or methyl, and Z is selected from following group:
14. film according to claim 13, wherein, the max transmissive of the 365nm wavelength illumination of described film ratio is about 92%.
15. film according to claim 13, wherein, the minimum transmittance of the radiation of visible light of the 400nm wavelength of described film is at least about 98%.
16. film according to claim 13 wherein, uses the swipe pencil hardness of the measured described film of described film of 6 kinds of pencils of 1H-6H to be at least 4H.
17. a color filter, described color filter comprises the film of the substantially transparent that derives from the self-curing multipolymer, and described self-curing multipolymer contains the structural unit shown in formula 1, formula 2, formula 3 and the formula 4:
In the formula 1, R
1Be hydrogen atom or methyl, and n is 1 to 10 integer;
In the formula 2, R
2Be hydrogen atom or methyl, and m is 1 to 10 integer;
In the formula 3, R
3Be hydrogen atom or methyl; With
In the formula 4, R
4Be hydrogen atom or methyl, and Z is selected from following group:
18. a color filter, described color filter comprise the film of the substantially transparent that uses compositions of thermosetting resin formation, described compositions of thermosetting resin contains organic solvent and contains the self-curing multipolymer of the structural unit shown in formula 1, formula 2, formula 3 and the formula 4:
In the formula 1, R
1Be hydrogen atom or methyl, and n is 1 to 10 integer;
In the formula 2, R
2Be hydrogen atom or methyl, and m is 1 to 10 integer;
In the formula 3, R
3Be hydrogen atom or methyl; With
In the formula 4, R
4Be hydrogen atom or methyl, and Z is selected from following group:
19. an imageing sensor that comprises color filter, described color filter comprises the film of the substantially transparent that derives from the self-curing multipolymer, and described self-curing multipolymer contains the structural unit shown in formula 1, formula 2, formula 3 and the formula 4:
In the formula 1, R
1Be hydrogen atom or methyl, and n is 1 to 10 integer;
In the formula 2, R
2Be hydrogen atom or methyl, and m is 1 to 10 integer;
In the formula 3, R
3Be hydrogen atom or methyl; With
In the formula 4, R
4Be hydrogen atom or methyl, and Z is selected from following group:
20. an imageing sensor that comprises color filter, described color filter comprise the film that uses the substantially transparent that compositions of thermosetting resin forms, described compositions of thermosetting resin contain organic solvent and contain formula 1,
The self-curing multipolymer of the structural unit shown in formula 2, formula 3 and the formula 4:
In the formula 1, R
1Be hydrogen atom or methyl, and n is 1 to 10 integer;
In the formula 2, R
2Be hydrogen atom or methyl, and m is 1 to 10 integer;
In the formula 3, R
3Be hydrogen atom or methyl; With
In the formula 4, R
4Be hydrogen atom or methyl, and Z is selected from following group:
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2007-0059842 | 2007-06-19 | ||
| KR1020070059842A KR100835605B1 (en) | 2007-06-19 | 2007-06-19 | Thermosetting resin composition for color filter of cmos image sensor and color filter using the composition, and cmos image sensor using the color filter |
| KR1020070059842 | 2007-06-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101329420A true CN101329420A (en) | 2008-12-24 |
| CN101329420B CN101329420B (en) | 2010-10-13 |
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| CN2008100848091A Expired - Fee Related CN101329420B (en) | 2007-06-19 | 2008-03-18 | Thermosetting resin composition for preparing color filter and color filter as well as sensor |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP4726917B2 (en) |
| KR (1) | KR100835605B1 (en) |
| CN (1) | CN101329420B (en) |
| TW (1) | TWI378321B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107356998A (en) * | 2016-05-10 | 2017-11-17 | 住友化学株式会社 | Optical film and the flexible apparatus using the optical film |
| CN112708019A (en) * | 2019-10-25 | 2021-04-27 | 乐凯化学材料有限公司 | Water-soluble color stabilizer for color photographic paper and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5526817B2 (en) * | 2010-01-29 | 2014-06-18 | 凸版印刷株式会社 | Color filter substrate manufacturing method and liquid crystal display device |
| JP5736691B2 (en) * | 2010-08-31 | 2015-06-17 | 大日本印刷株式会社 | Color filter for liquid crystal display |
| KR101466147B1 (en) | 2011-12-05 | 2014-11-27 | 제일모직 주식회사 | Photosensitive resin composition for color filter and color filter using the same |
| TWI579330B (en) * | 2012-05-23 | 2017-04-21 | Sumitomo Chemical Co | Curable resin composition |
| KR101618685B1 (en) | 2012-10-11 | 2016-05-09 | 제일모직 주식회사 | Photosensitive resin composition for color filter and color filter using the same |
| KR101618689B1 (en) | 2012-12-24 | 2016-05-09 | 제일모직 주식회사 | Photosensitive resin composition for color filter and color filter using the same |
| WO2014157214A1 (en) | 2013-03-29 | 2014-10-02 | 新日鉄住金化学株式会社 | Polyfunctional (meth)acrylic acid ester copolymer, and curable resin composition and cured product thereof |
| JP6578775B2 (en) * | 2015-07-16 | 2019-09-25 | 東洋インキＳｃホールディングス株式会社 | Coloring composition for color filter, and color filter |
| KR101603565B1 (en) * | 2015-09-10 | 2016-03-16 | 영창케미칼 주식회사 | Developer Composition For Color Filter Image Sensor |
| KR102247290B1 (en) * | 2018-07-27 | 2021-04-30 | 주식회사 엘지화학 | Binder resin, photosensitive resin composition, pothoresist, color filter and display device |
| KR102216766B1 (en) * | 2018-11-23 | 2021-02-16 | 주식회사 엘지화학 | Photosensitive resin composition, photoresist, color filter and display device |
| KR102679740B1 (en) | 2022-01-25 | 2024-06-28 | 케이피엑스케미칼 주식회사 | One-component thermosetting resin composition and function membrane comprising the same |
| WO2024029204A1 (en) * | 2022-08-03 | 2024-02-08 | 住友化学株式会社 | Colored curable resin composition, color filter, display device, and solid-state image pickup element |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5919601A (en) | 1996-11-12 | 1999-07-06 | Kodak Polychrome Graphics, Llc | Radiation-sensitive compositions and printing plates |
| KR100493961B1 (en) * | 1999-08-17 | 2005-06-10 | 주식회사 엘지화학 | Photosensitive resin composition |
| KR100442865B1 (en) | 2001-11-07 | 2004-08-02 | 삼성전자주식회사 | Photosensitive polymer having fluorinated ethylene glycol group and chemically amplified resist composition comprising the same |
| KR100574956B1 (en) * | 2003-11-20 | 2006-04-28 | 삼성전자주식회사 | Voltage reference clock generating circuit capable of generating voltage reference clock synchronized with system clock and method thereof |
| JP4864375B2 (en) * | 2004-08-09 | 2012-02-01 | ドンジン セミケム カンパニー リミテッド | Photosensitive resin composition for spacer, spacer and liquid crystal display element |
| KR100642446B1 (en) * | 2004-10-15 | 2006-11-02 | 제일모직주식회사 | Thermosetting One-Solution Type Composition For Protective Film Of Color Filter And Color Filter By Using The Same |
| WO2006134740A1 (en) * | 2005-06-17 | 2006-12-21 | Toppan Printing Co., Ltd. | Imaging element |
| KR100805688B1 (en) * | 2005-09-15 | 2008-02-21 | 제일모직주식회사 | Thermosetting One-Solution type Composition for Protective Film of Color Filter and Color Filter by using the Same |
| JP2007090782A (en) * | 2005-09-29 | 2007-04-12 | Dainippon Printing Co Ltd | Protective layer transfer sheet, and printed object |
| JP4421566B2 (en) * | 2005-12-26 | 2010-02-24 | チェイル インダストリーズ インコーポレイテッド | Hard mask composition for photoresist underlayer film and method of manufacturing semiconductor integrated circuit device using the same |
| KR100758879B1 (en) * | 2006-07-13 | 2007-09-14 | 제일모직주식회사 | One-solution type thermosetting composition for protective film of color filter |
-
2007
- 2007-06-19 KR KR1020070059842A patent/KR100835605B1/en active IP Right Grant
-
2008
- 2008-01-31 JP JP2008021344A patent/JP4726917B2/en active Active
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107356998A (en) * | 2016-05-10 | 2017-11-17 | 住友化学株式会社 | Optical film and the flexible apparatus using the optical film |
| CN112708019A (en) * | 2019-10-25 | 2021-04-27 | 乐凯化学材料有限公司 | Water-soluble color stabilizer for color photographic paper and preparation method thereof |
| CN112708019B (en) * | 2019-10-25 | 2024-04-30 | 乐凯化学材料有限公司 | Water-soluble color stabilizer for color photographic paper and preparation method thereof |
Also Published As
| Publication number | Publication date |
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| KR100835605B1 (en) | 2008-06-09 |
| JP2009001770A (en) | 2009-01-08 |
| CN101329420B (en) | 2010-10-13 |
| TW200900855A (en) | 2009-01-01 |
| TWI378321B (en) | 2012-12-01 |
| JP4726917B2 (en) | 2011-07-20 |
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