WO2012105288A1 - マイクロレンズ形成用感光性樹脂組成物 - Google Patents
マイクロレンズ形成用感光性樹脂組成物 Download PDFInfo
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- WO2012105288A1 WO2012105288A1 PCT/JP2012/050479 JP2012050479W WO2012105288A1 WO 2012105288 A1 WO2012105288 A1 WO 2012105288A1 JP 2012050479 W JP2012050479 W JP 2012050479W WO 2012105288 A1 WO2012105288 A1 WO 2012105288A1
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- photosensitive resin
- resin composition
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- 0 C*(C)C(C(*(C)C)C(N1*)=O)C1=O Chemical compound C*(C)C(C(*(C)C)C(N1*)=O)C1=O 0.000 description 2
Classifications
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F12/00—Homopolymers and 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 aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
- C08F12/22—Oxygen
- C08F12/24—Phenols or alcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—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 aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—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 aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/12—Monomers containing a branched unsaturated aliphatic radical or a ring substituted by an alkyl radical
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—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 aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—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 aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
- C08F212/22—Oxygen
- C08F212/24—Phenols or alcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—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 aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/32—Monomers containing only one unsaturated aliphatic radical containing two or more rings
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F216/00—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 alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F216/12—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 alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
- C08F216/14—Monomers containing only one unsaturated aliphatic radical
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F216/00—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 alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F216/12—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 alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
- C08F216/14—Monomers containing only one unsaturated aliphatic radical
- C08F216/1416—Monomers containing oxygen in addition to the ether oxygen, e.g. allyl glycidyl ether
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F232/08—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having condensed rings
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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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/36—Amides or imides
- C08F222/40—Imides, e.g. cyclic imides
Definitions
- the present invention relates to a photosensitive resin composition for forming a microlens and a microlens formed from the photosensitive resin composition.
- a microlens mounted on an image sensor is manufactured using a photosensitive resin composition.
- such microlenses are formed in a favorable pattern shape, in addition to transparency, heat resistance, and solvent resistance, to suppress coloring due to high-temperature heating to prevent deterioration of transparency (heat resistance discoloration).
- Various characteristics such as the patterning (patterning) are required.
- a photosensitive resin composition used here conventionally, a photosensitive resin composition for forming a microlens containing a hydroxystyrene copolymer or polyhydroxystyrene is known.
- Patent Documents 1 to 4 a photoresist composition containing a maleimide copolymer, an antireflection film-forming composition, a material for forming a resist protective film for immersion lithography, and the like have been proposed (Patent Documents 1 to 4).
- insulating films for display devices such as liquid crystal displays (LCDs) and organic electroluminescence display devices
- alkali-soluble copolymers comprising indene, maleimide and N-substituted maleimide, 1,2-naphthoquinonediazide compounds
- a method for forming an insulating film for a display device, which uses a radiation-sensitive resin composition containing a crosslinking agent has been proposed (Patent Document 5).
- a maleimide copolymer comprising a monomer structural unit derived from styrene, a monomer structural unit derived from styrenes, and a monomer structure derived from (meth) acrylic acid (patent) Reference 6).
- [A] (a1) unsaturated carboxylic acid and / or unsaturated carboxylic anhydride, (a2) epoxy group-containing unsaturated compound, (a3) maleimide monomer and (a4) other olefinically unsaturated compound
- a radiation-sensitive resin composition characterized in that it contains a polymer and a [B] 1,2-quinonediazide compound has been reported (Patent Document 7).
- Patent Document 7 it is explained that the radiation-sensitive resin composition reported in this document can provide a high radiation sensitivity and can easily form a patterned thin film excellent in solvent resistance, heat resistance, transparency, and heat discoloration. However, it does not suggest the specific shape accuracy of the pattern formed from the composition. Further, no unsubstituted maleimide is described as a maleimide monomer.
- a conventional microlens produced using a conventional hydroxystyrene-based copolymer or a photosensitive resin composition for forming a microlens containing polyhydroxystyrene tends to be colored by high-temperature heating, so that the transparency tends to decrease.
- the present invention has been made based on the above circumstances, and the problems to be solved are the transparency of the cured film, the heat resistance, the heat discoloration resistance, the solvent resistance, and the patterning property of the photosensitive resin film. It is providing the photosensitive resin composition for microlens formation which can improve remarkably.
- the present inventors have completed the present invention. That is, it is a photosensitive resin composition for forming a microlens containing the component (A), the component (B), the component (C) and a solvent.
- X represents a hydrocarbon group having 1 to 20 carbon atoms
- Y represents an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, a phenyl group, or a benzyl group
- Z represents a phenyl group, a naphthyl group, an anthracenyl group, a biphenylyl group or an alkoxy group having 1 to 8 carbon atoms, provided that the group represented by X may have an ether bond or a cyclic structure
- part or all of the hydrogen atoms may be substituted with a halogen
- the film formed from the photosensitive resin composition for forming a microlens of the present invention can have excellent transparency, heat resistance, heat discoloration resistance, and solvent resistance. Moreover, the pattern formed from the photosensitive resin composition for microlens formation of this invention can also have the outstanding heat resistance.
- the film formed from the photosensitive resin composition for forming a microlens of the present invention has a microlens when heat treatment is performed at a high temperature in the formation process or the formation process of peripheral devices such as wiring. The possibility of coloring and deformation of the lens shape can be significantly reduced.
- the electrode and wiring forming process is performed after the microlens is formed, problems such as deformation and peeling of the microlens due to the organic solvent can be significantly reduced. Therefore, the photosensitive resin composition for forming a microlens of the present invention is suitable as a material for forming a microlens.
- the present invention relates to a copolymer comprising a maleimide structural unit as component (A) and a vinyl ether structural unit having a hydroxy group, a photosensitive agent as component (B), a crosslinking agent as component (C), and a solvent. It is a photosensitive resin composition for lens formation.
- the solid content obtained by removing the solvent from the photosensitive resin composition for forming a microlens of the present invention is usually 1% by mass to 50% by mass.
- the copolymer as the component (A) in the composition of the present invention includes a maleimide structural unit represented by the formula (1), a vinyl ether structural unit represented by the formula (2), and the formula (3), It is a copolymer which has at least 1 sort (s) among 3 types of structural units represented by Formula (4) and Formula (5).
- the vinyl ether structural unit represented by the formula (2) as an example in which the X represents a hydrocarbon group having 1 to 20 carbon atoms having an ether bond or a cyclic structure, the following formula (2-1) ) And formula (2-2).
- R 1 and R 2 each independently represent a linear or branched alkylene group having 1 to 7 carbon atoms or a single bond
- R 3 and R 4 each independently represent a linear or branched group. Represents a chain-like alkylene group having 1 to 10 carbon atoms.
- the cyclohexylene group in the formula is directly bonded to an oxygen atom and a hydroxy group.
- Examples of the hydrocarbon group having 1 to 20 carbon atoms which may have an ether bond or a cyclic structure represented by X in the formula (2) include, for example, a methylene group, an ethylene group, a trimethylene group, and a tetramethylene group.
- Examples include a propylene ether group, a methylene propylene ether group, and a diisopropylene ether group.
- the vinyl ether structural unit represented by the formula (2) is characterized by having a hydroxy group as a cross-linking site in the side chain. Therefore, the composition of the present invention containing the copolymer having the structural unit has good crosslinking efficiency and improved curability, and the lens pattern produced by development is excellent in shape maintaining characteristics.
- vinyl ether compound forming the vinyl ether structural unit examples include 2-hydroxyethyl vinyl ether, 3-hydroxypropyl vinyl ether, 4-hydroxybutyl vinyl ether, 5-hydroxypentyl vinyl ether, 6-hydroxyhexyl vinyl ether, 4-hydroxy Examples thereof include cyclohexyl vinyl ether, 1,4-cyclohexanedimethanol monovinyl ether, diethylene glycol monovinyl ether, and dipropylene glycol monovinyl ether. These vinyl ether compounds may be used alone or in combination of two or more.
- the structural unit represented by the formula (1) is 20 mol% to 80 mol% with respect to the sum of the contents of at least one of the three structural units represented by the formula (5), preferably Is 25 mol% to 70 mol%
- the content of the structural unit represented by the formula (2) is 5 mol% to 65 mol%, preferably 10 mol% to 55 mol%, and further the formulas (3) and (4).
- content of at least 1 sort (s) among the structural units represented by Formula (5) is 15 mol%-75 mol%, Preferably it is 20 mol%-65 mol%.
- the weight average molecular weight of the copolymer is, for example, 1000 to 50000, preferably 3000 to 30000.
- the weight average molecular weight is a value obtained by using gel as a standard sample by gel permeation chromatography (GPC).
- the content of the component (A) in the composition of the present invention is usually 1% by mass to 99% by mass, preferably 10% by mass to 95% by mass, based on the content in the solid content of the composition. is there.
- the method for obtaining the component (A) is not particularly limited.
- a monomer mixture containing the monomer species used for obtaining the above-described copolymer is usually 50 ° C. to 110 ° C. in a polymerization solvent. It is obtained by carrying out a polymerization reaction at a temperature of
- the photosensitive agent which is the component (B) in the composition of the present invention is not particularly limited as long as it is a compound that can be used as a photosensitive component, but a 1,2-naphthoquinonediazide compound is preferable.
- the 1,2-naphthoquinonediazide compound is a compound having a hydroxy group, and among these hydroxy groups, 10 mol% to 100 mol%, preferably 20 mol% to 95 mol% is 1,2-naphtho.
- a quinonediazide sulfonate ester compound can be used.
- Examples of the compound having a hydroxy group include phenol, o-cresol, m-cresol, p-cresol, hydroquinone, resorcinol, catechol, methyl gallate, ethyl gallate, 1,3,3-tris (4-hydroxy Phenyl) butane, 4,4′-isopropylidene diphenol, 1,1-bis (4-hydroxyphenyl) cyclohexane, 4,4′-dihydroxydiphenyl sulfone, 4,4 ′-(hexafluoroisopropylidene) diphenol, 4,4 ′, 4 ′′ -trishydroxyphenylethane, 1,1,1-trishydroxyphenylethane, 4,4 ′-[1- [4- [1- (4-hydroxyphenyl) -1-methylethyl ] Phenyl] ethylidene] bisphenol, 2,4-dihydroxybenzo Phenone, 2,3,4-trihydroxybenzophenone, 2,2
- These photosensitizers can be used alone or in combination of two or more.
- the content of the component (B) in the composition of the present invention is usually 1% by mass to 50% by mass based on the content in the solid content of the composition.
- the cross-linking agent as component (C) in the composition of the present invention is a compound that forms a bond with a compounded composition such as a resin or photosensitizer or other cross-linking agent molecules by the action of heat or acid.
- a compounded composition such as a resin or photosensitizer or other cross-linking agent molecules by the action of heat or acid.
- the crosslinking agent include a hydroxymethyl group-substituted phenol compound, a compound having an alkoxyalkylated amino group, and an epoxy compound. These crosslinking agents can be used alone or in combination of two or more.
- hydroxymethyl group-substituted phenol compound examples include 2-hydroxymethyl-4,6-dimethylphenol, 1,3,5-trihydroxymethylbenzene, 3,5-dihydroxymethyl-4-methoxytoluene [2,6 -Bis (hydroxymethyl) -p-cresol].
- Examples of the compound having an alkoxyalkylated amino group include (poly) methylolated melamine, (poly) methylolated glycoluril, (poly) methylolated benzoguanamine, (poly) methylolated urea, And a nitrogen-containing compound having a plurality of active methylol groups, wherein at least one hydrogen atom of the hydroxy group in the methylol group is substituted with an alkyl group such as a methyl group or a butyl group.
- the alkoxyalkylated amino group-containing compound may be a mixture in which a plurality of substituted compounds are mixed, and there is a mixture containing an oligomer component that is partially self-condensed, and such a mixture is also used. be able to. More specifically, for example, hexamethoxymethyl melamine (manufactured by Nippon Cytec Industries, Ltd., CYMEL (registered trademark) 303), tetrabutoxymethyl glycoluril (manufactured by Nippon Cytec Industries, Ltd., CYMEL (registered trademark) 1170).
- CYMEL series products such as tetramethoxymethylbenzoguanamine (CYCEL (registered trademark) 1123, manufactured by Nippon Cytec Industries Co., Ltd.), methylated melamine resin (manufactured by Sanwa Chemical Co., Ltd., Nicalac (registered trademark) MW-30HM, MW-390, MW-100LM, MX-750LM), methylated urea resin (manufactured by Sanwa Chemical Co., Ltd., Nicalac (registered trademark) MX-270, MX-280, MX-290), etc. List the products of the Nicarak series It can be.
- CYCEL registered trademark
- methylated melamine resin manufactured by Sanwa Chemical Co., Ltd., Nicalac (registered trademark) MW-30HM, MW-390, MW-100LM, MX-750LM
- methylated urea resin manufactured by Sanwa Chemical Co., Ltd., Nicalac (registered trademark
- epoxy compound examples include the following commercial products, but are not limited to these examples.
- examples of the bisphenol A type epoxy resin include jER (registered trademark) 828, 834, 1001, and 1004 (above, manufactured by Mitsubishi Chemical Corporation), EPICLON (registered trademark) 850, 860, and 4055 (or more). DIC Corporation).
- examples of the bisphenol F type epoxy resin include jER (registered trademark) 807 (manufactured by Mitsubishi Chemical Corporation) and EPICLON (registered trademark) 830 (manufactured by DIC Corporation).
- phenol novolac type epoxy resins examples include EPICLON (registered trademark) N-740, N ⁇ -770, N-775 (manufactured by DIC Corporation), jER (registered trademark) 152, 154 (and above, Mitsubishi). Chemical Co., Ltd.).
- cresol novolak type epoxy resin examples include EPICLON (registered trademark) N-660, N-665, N-670, N-673, N-680, N-695, and N-665-EXP. N-672-EXP (above, manufactured by DIC Corporation).
- Examples of the glycidylamine type epoxy resin include EPICLON (registered trademark) 430, 430-L (above, manufactured by DIC Corporation), TETRAD (registered trademark) -C, TETRAD (registered trademark) -X (above, Mitsubishi). Gas Chemical Co., Ltd.), jER (registered trademark) 604, 630 (above, manufactured by Mitsubishi Chemical Corporation), Sumiepoxy (registered trademark) ELM120, ELM100, ELM434, ELM434HV (above, Sumitomo Chemical Co., Ltd.) And Epototo (registered trademark) YH-434, YH-434L (above, manufactured by Tohto Kasei Co., Ltd.).
- Examples of the alicyclic epoxy resin include Denacol (registered trademark) EX-252 (manufactured by Nagase Chemmutex Co., Ltd.), EPICLON (registered trademark) 200, 400 (manufactured by DIC Corporation), and jER (registered). Trademarks) 871 and 872 (above, manufactured by Mitsubishi Chemical Corporation).
- Epoxy resins having a cyclohexene oxide structure include, for example, Epolide (registered trademark) GT-401, GT-403, GT-301, GT-302, Celoxide (registered trademark) 2021, 3000 (above, Daicel Chemical). Kogyo Co., Ltd.).
- a compound having an alkoxyalkylated amino group is preferable.
- the content of the component (C) in the composition of the present invention is usually 1% by mass to 50% by mass based on the content in the solid content of the composition.
- the method for preparing the composition of the present invention is not particularly limited.
- the copolymer (A) is dissolved in a solvent, and the solution is the photosensitive agent (B) and the component (C).
- the solution is the photosensitive agent (B) and the component (C).
- a crosslinking agent is mixed at a predetermined ratio to obtain a uniform solution.
- other additives are further added and mixed as necessary.
- the solvent is not particularly limited as long as it dissolves the component (A), the component (B), and the component (C).
- solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate.
- solvents can be used alone or in combination of two or more.
- propylene glycol monomethyl ether propylene glycol monomethyl ether acetate, 2-heptanone, ethyl lactate, butyl lactate and cyclohexanone are preferable from the viewpoint of improving the leveling property of the coating film.
- the composition of the present invention may contain a surfactant for the purpose of improving the coating property.
- the surfactant include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene alkyl ethers such as polyoxyethylene oleyl ether, polyoxyethylene octylphenol ether, polyoxyethylene Polyoxyethylene alkyl aryl ethers such as nonylphenol ether, polyoxyethylene / polyoxypropylene block copolymers, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, sorbitan tristearate Sorbitan fatty acid esters such as rate, polyoxyethylene sorbitan monolaurate, polyoxyethylene Non-ionic surfactants such as polyoxyethylene sorbitan fatty acid esters such as sorbitan monopalmitate, polyoxyethylene sorbitan monostearate,
- the surfactants can be used alone or in combination of two or more.
- the content in the composition of this invention is 3 mass% or less based on content in the solid content of the said composition, Preferably it is 1 mass% or less. More preferably, it is 0.5 mass% or less.
- composition of the present invention may contain additives such as curing aids, ultraviolet absorbers, sensitizers, plasticizers, antioxidants, adhesion aids and the like as long as the effects of the present invention are not impaired. Can be included.
- Substrate for example, a semiconductor substrate such as silicon covered with a silicon oxide film, a semiconductor substrate such as silicon covered with a silicon nitride film or a silicon oxynitride film, a silicon nitride substrate, a quartz substrate, a glass substrate (non-alkali glass, low A glass substrate on which an ITO film is formed ⁇ , and the composition of the present invention is applied by an appropriate application method such as a spinner or a coater, and then a heating means such as a hot plate is applied. By using and prebaking, a coating film is formed.
- the pre-baking conditions are appropriately selected from a baking temperature of 80 ° C. to 250 ° C. and a baking time of 0.3 minutes to 60 minutes, preferably at a baking temperature of 80 ° C. to 150 ° C. and a baking time of 0.5 minutes to 5 minutes. is there.
- the film thickness of the film formed from the composition of the present invention is 0.005 ⁇ m to 5.0 ⁇ m, preferably 0.01 ⁇ m to 3.0 ⁇ m.
- a mask for forming a predetermined pattern.
- ultraviolet rays such as g-line and i-line, and far-infrared rays such as KrF excimer laser can be used.
- post-exposure heating Post Exposure Bake
- the conditions for the post-exposure heating are appropriately selected from heating temperatures of 80 ° C. to 150 ° C. and heating times of 0.3 minutes to 60 minutes. Then, it is developed with an alkaline developer.
- alkaline developer examples include aqueous solutions of alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, aqueous solutions of quaternary ammonium hydroxides such as tetramethylammonium hydroxide, tetraethylammonium hydroxide and choline, and ethanolamine. And alkaline aqueous solutions such as amine aqueous solutions such as propylamine and ethylenediamine. Further, a surfactant can be added to these developers.
- alkali metal hydroxides such as potassium hydroxide and sodium hydroxide
- quaternary ammonium hydroxides such as tetramethylammonium hydroxide, tetraethylammonium hydroxide and choline
- alkaline aqueous solutions such as amine aqueous solutions such as propylamine and ethylenediamine.
- a surfactant can be added to these developers.
- the development conditions are appropriately selected from a development temperature of 5 ° C. to 50 ° C. and a development time of 10 seconds to 300 seconds.
- the film formed from the composition of the present invention can be easily developed at room temperature using an aqueous tetramethylammonium hydroxide solution. After development, for example, rinsing is performed using ultrapure water.
- the entire surface of the substrate is exposed using a g-line, i-line, or KrF excimer laser. Thereafter, post-baking is performed using a heating means such as a hot plate.
- the post-bake conditions are appropriately selected from, for example, a baking temperature of 100 ° C. to 250 ° C. and a baking time of 0.5 minutes to 60 minutes.
- the reaction solution was cooled to room temperature and then poured into diethyl ether to reprecipitate the polymer and dried under reduced pressure to obtain a polymer (copolymer) having a structural unit represented by the following formula (5).
- the weight average molecular weight Mw of the obtained polymer was 9,000 (polystyrene conversion).
- the reaction solution was cooled to room temperature and then poured into diethyl ether to reprecipitate the polymer and dried under reduced pressure to obtain a polymer (copolymer) having a structural unit represented by the following formula (6).
- the weight average molecular weight Mw of the obtained polymer was 4,500 (in terms of polystyrene).
- the reaction solution was cooled to room temperature and then poured into acetonitrile to reprecipitate the polymer and dried under reduced pressure to obtain a polymer (copolymer) having a structural unit represented by the following formula (7).
- the weight average molecular weight Mw of the obtained polymer was 28,000 (polystyrene conversion).
- the reaction solution was cooled to room temperature and then poured into diethyl ether to reprecipitate the polymer and dried under reduced pressure to obtain a polymer (copolymer) having a structural unit represented by the following formula (8).
- the weight average molecular weight Mw of the obtained polymer was 8,000 (polystyrene conversion).
- Example 1 4.0 g of the polymer as component (A) obtained in Synthesis Example 1, 1.2 g of P-200 (manufactured by Toyo Gosei Co., Ltd.) as the photosensitive agent as component (B), and crosslinking as component (C) MX-750LM (manufactured by Sanwa Chemical Co., Ltd.) 1.2 g as the agent, Megafac (registered trademark) R-30 (manufactured by DIC Corporation) 0.02 g as the surfactant, 28.0 g of propylene glycol monomethyl ether and A solution was prepared by dissolving in 12.0 g of ethyl lactate. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and prepared the photosensitive resin composition for microlens formation.
- Example 2 A microlens-forming photosensitive resin composition was prepared under the same conditions as in Example 1 except that 4.0 g of the polymer obtained in Synthesis Example 2 was used as the component (A).
- Example 3 A photosensitive resin composition for forming a microlens was prepared under the same conditions as in Example 1 except that 4.0 g of the polymer obtained in Synthesis Example 3 was used as the component (A).
- Example 4 A microlens-forming photosensitive resin composition was prepared under the same conditions as in Example 1 except that 4.0 g of the polymer obtained in Synthesis Example 4 was used as the component (A).
- the transmittance of this film at a wavelength of 400 nm was measured using an ultraviolet-visible spectrophotometer UV-2550 (manufactured by Shimadzu Corporation). Furthermore, after heating this film
- the film formed from the photosensitive resin composition for forming a microlens of the present invention had high heat resistance and was hardly colored even after being heated at 260 ° C.
- the film formed from the photosensitive resin composition prepared in Comparative Example 1 had a film transmittance of 95% after post-baking at 200 ° C. for 5 minutes, but was further heated at 260 ° C. for 5 minutes. Then, the transmittance
- the transmittance of the film is usually required to be 90% or more, and it is desirable that the transmittance hardly changes even after heating, but Comparative Example 1 did not satisfy this requirement.
- each pattern was observed after development, rinsing and drying, after the post-baking, and after heating at 260 ° C.
- the pattern shape after post-baking and after heating at 260 ° C. is a shape that maintains the lens pattern shape after development, rinsing, and drying. It was confirmed that.
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Abstract
Description
かかるマイクロレンズにあっては、一般に、透明性、耐熱性、耐溶剤性に加え、高温加熱による着色を抑制し透明性の低下を防ぐこと(耐熱変色性)、並びに良好なパターン形状に形成されていること(パターニング性)等の諸特性が要求されている。ここで用いられる感光性樹脂組成物としては、従来、ヒドロキシスチレン系共重合体又はポリヒドロキシスチレンを含有するマイクロレンズ形成用感光性樹脂組成物が知られている。
さらに、多官能(メタ)アクリレートとの相溶性に非常に優れ、また、アルカリ可溶性も良好であり、したがって、このような特徴が要求される各種用途に好適に用いることを目的に、無置換マレイミド由来の単量体構造単位、スチレン類由来の単量体構造単位、(メタ)アクリル酸由来の単量体構造を含有することを特徴とする、マレイミド系共重合体が提案されている(特許文献6)。
しかし、これら従来文献は、マイクロレンズ形成用感光性樹脂組成物としての用途の提供を目的とするものでなく、かつ、無置換マレイミド構造単位、及びビニルエーテル構造単位を有する共重合体のマイクロレンズ形成用感光性樹脂組成物への適用について具体的な手段及び効果は示唆されていない。
本発明は、前記の事情に基づいてなされたものであり、その解決しようとする課題は、硬化膜の透明性、耐熱性、耐熱変色性、及び耐溶剤性、並びに感光性樹脂膜のパターニング性を著しく改善することができるマイクロレンズ形成用感光性樹脂組成物を提供することである。
すなわち、(A)成分、(B)成分、(C)成分及び溶剤を含有するマイクロレンズ形成用感光性樹脂組成物である。
(A)成分:下記式(1)で表されるマレイミド構造単位、下記式(2)で表されるビニルエーテル構造単位、並びに下記式(3)、式(4)及び式(5)で表される構造単位3種のうち少なくとも1種を有する共重合体
(B)成分:感光剤
(C)成分:架橋剤
本発明の他の態様は、前記マイクロレンズ形成用感光性樹脂組成物から得られる硬化膜である。
さらに他の態様は、前記マイクロレンズ形成用感光性樹脂組成物から作製されるマイクロレンズである。
また、本発明のマイクロレンズ形成用感光性樹脂組成物から形成されたパターンも優れた耐熱性を有することが可能である。
以上より、本発明のマイクロレンズ形成用感光性樹脂組成物から形成される膜は、その形成工程、又は配線等の周辺装置の形成工程において、高温での加熱処理が行われる場合にマイクロレンズが着色し、レンズ形状が変形する可能性を著しく減少できる。また、マイクロレンズ形成後に電極、配線形成工程が行われる場合には、有機溶剤によるマイクロレンズの変形、剥離といった問題も著しく減少できる。
したがって、本発明のマイクロレンズ形成用感光性樹脂組成物は、マイクロレンズを形成する材料として好適である。
以下、各成分の詳細を説明する。
本発明のマイクロレンズ形成用感光性樹脂組成物から溶剤を除いた固形分は通常、1質量%乃至50質量%である。
本発明の組成物における(A)成分である共重合体は、前記式(1)で表されるマレイミド構造単位、前記式(2)で表されるビニルエーテル構造単位、並びに前記式(3)、式(4)及び式(5)で表される構造単位3種のうち少なくとも1種を有する共重合体である。
上記式(2-1)において、R1及びR2が単結合を表す場合、式中のシクロヘキシレン基は酸素原子及びヒドロキシ基と直接結合する。
本発明の組成物における(B)成分である感光剤としては、感光成分として使用できる化合物であれば、特に限定されるものでないが、1,2-ナフトキノンジアジド化合物が好ましい。前記1,2-ナフトキノンジアジド化合物としては、ヒドロキシ基を有する化合物であって、これらのヒドロキシ基のうち、10モル%乃至100モル%、好ましくは20モル%乃至95モル%が1,2-ナフトキノンジアジドスルホン酸エステル化された化合物を用いることができる。
〔下記合成例で得られたポリマーの重量平均分子量の測定〕
装置:日本分光(株)製GPCシステム
カラム:Shodex〔登録商標〕KL-804L及び803L
カラムオーブン:40℃
流量:1ml/分
溶離液:テトラヒドロフラン
<合成例1>
マレイミド16.0g、インデン23.9g、2-ヒドロキシエチルビニルエーテル3.6g、及び2,2’-アゾビスイソブチロニトリル1.3gをプロピレングリコールモノメチルエーテル104.7gに溶解させた後、この溶液を、プロピレングリコールモノメチルエーテル30.0gを80℃に保持したフラスコ中に4時間かけて滴下した。滴下終了後、18時間反応させた。この反応溶液を室温に冷却後、ジエチルエーテルに投入してポリマーを再沈殿させ、減圧乾燥して、下記式(5)で表される構造単位を有するポリマー(共重合体)を得た。
得られたポリマーの重量平均分子量Mwは9,000(ポリスチレン換算)であった。
マレイミド8.0g、N-シクロヘキシルマレイミド14.8g、1,4-シクロヘキサンジメタノールモノビニルエーテル18.7g、及び2,2’-アゾビスイソブチロニトリル1.2gをプロピレングリコールモノメチルエーテル99.7gに溶解させた後、この溶液を、プロピレングリコールモノメチルエーテル28.5gを80℃に保持したフラスコ中に4時間かけて滴下した。滴下終了後、18時間反応させた。この反応溶液を室温に冷却後、ジエチルエーテルに投入してポリマーを再沈殿させ、減圧乾燥して、下記式(6)で表される構造単位を有するポリマー(共重合体)を得た。
得られたポリマーの重量平均分子量Mwは4,500(ポリスチレン換算)であった。
マレイミド12.0g、4-tert-ブチルスチレン19.8g、1,4-シクロヘキサンジメタノールモノビニルエーテル10.5g、及び2,2’-アゾビスイソブチロニトリル1.3gをプロピレングリコールモノメチルエーテル101.8gに溶解させた後、この溶液を、プロピレングリコールモノメチルエーテル29.1gを80℃に保持したフラスコ中に4時間かけて滴下した。滴下終了後、18時間反応させた。この反応溶液を室温に冷却後、アセトニトリルに投入してポリマーを再沈殿させ、減圧乾燥して、下記式(7)で表される構造単位を有するポリマー(共重合体)を得た。
得られたポリマーの重量平均分子量Mwは28,000(ポリスチレン換算)であった。
マレイミド13.0g、2-ビニルナフタレン25.8g、ジエチレングリコールモノビニルエーテル4.4g、及び2,2’-アゾビスイソブチロニトリル2.1gをプロピレングリコールモノメチルエーテル106.0gに溶解させた後、この溶液を、プロピレングリコールモノメチルエーテル30.3gを80℃に保持したフラスコ中に4時間かけて滴下した。滴下終了後、18時間反応させた。この反応溶液を室温に冷却後、ジエチルエーテルに投入してポリマーを再沈殿させ、減圧乾燥して、下記式(8)で表される構造単位を有するポリマー(共重合体)を得た。
得られたポリマーの重量平均分子量Mwは8,000(ポリスチレン換算)であった。
<実施例1>
合成例1で得られた(A)成分であるポリマー4.0g、(B)成分である感光剤としてP-200(東洋合成工業(株)製)1.2g、(C)成分である架橋剤としてMX-750LM((株)三和ケミカル製)1.2g、界面活性剤としてメガファック(登録商標)R-30(DIC(株)製)0.02gをプロピレングリコールモノメチルエーテル28.0g及び乳酸エチル12.0gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過してマイクロレンズ形成用感光性樹脂組成物を調製した。
(A)成分として合成例2で得られたポリマー4.0gを用いた以外は上記実施例1と同じ条件で、マイクロレンズ形成用感光性樹脂組成物を調製した。
(A)成分として合成例3で得られたポリマー4.0gを用いた以外は上記実施例1と同じ条件で、マイクロレンズ形成用感光性樹脂組成物を調製した。
(A)成分として合成例4で得られたポリマー4.0gを用いた以外は上記実施例1と同じ条件で、マイクロレンズ形成用感光性樹脂組成物を調製した。
下記式(9)で表される構造単位を有するポリ(4-ビニルフェノール)(シグマアルドリッチジャパン(株)製、重量平均分子量Mw20,000)4.0g、感光剤としてP-200(東洋合成工業(株)製)1.2g、架橋剤としてMX-750LM((株)三和ケミカル製)1.2g、及び界面活性剤としてメガファック(登録商標)R-30(DIC(株)製)0.02gを、プロピレングリコールモノメチルエーテル33.0g及び乳酸エチル14.0gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過してマイクロレンズ形成用感光性樹脂組成物を調製した。
実施例1乃至実施例4及び比較例1で調製した感光性樹脂組成物をそれぞれ、石英基板上にスピンコーターを用いて塗布し、ホットプレート上において100℃で3分間プリベークした。次いで、紫外線照射装置PLA-501(F)(キャノン(株)製)により、365nmにおける照射量が500mJ/cm2の紫外線を全面照射した(フォトブリーチング)。次いで、ホットプレート上において200℃で5分間ポストベークを行い、膜厚600nmの膜を形成した。この膜を紫外線可視分光光度計UV-2550((株)島津製作所製)を用いて波長400nmの透過率を測定した。さらにこの膜を260℃で5分間加熱した後、波長400nmの透過率を測定した。評価の結果を表1に示す。
実施例1乃至実施例4で調製した感光性樹脂組成物をそれぞれ、シリコンウエハー上にスピンコーターを用いて塗布し、ホットプレート上において100℃で90秒間プリベークして、膜厚600nmの感光性樹脂膜を形成した。次いで、i線ステッパーNSR-2205i12D(NA=0.63)((株)ニコン製)を用いて、グレースケールマスクを介して露光した。次いで、ホットプレート上において、100℃で90秒間露光後ベーク(PEB)し、水酸化テトラメチルアンモニウム(TMAH)水溶液(実施例1で調製した感光性樹脂組成物を用いた場合は0.2質量%、実施例2乃至実施例4で調製した感光性樹脂組成物を用いた場合は1.0質量%)で60秒間現像し、超純水で20秒間リンス、乾燥して2.0μm径のレンズパターンを形成した。さらに、前記i線ステッパーを用いて、500mJ/cm2のi線を全面照射し(フォトブリーチング)、ホットプレート上においてポストベーク(まず140℃~160℃で5分間ベーク、その後200℃で5分間ベーク)を行った。さらに、この膜を260℃で5分間加熱した。走査型電子顕微鏡S-4800((株)日立ハイテクノロジーズ製)を用いて、現像・リンス・乾燥後、前記ポストベーク後、及び260℃加熱後それぞれのパターンの観察を行った。実施例1乃至実施例4で調製したいずれの感光性樹脂組成物を用いた場合も、ポストベーク後及び260℃加熱後のパターン形状は、現像・リンス・乾燥後のレンズパターン形状を維持した形状であることを確認した。
実施例1乃至実施例4で調製した感光性樹脂組成物をそれぞれ、シリコンウエハー上にスピンコーターを用いて塗布し、ホットプレート上において100℃で3分間プリベークした。次いで、紫外線照射装置PLA-501(F)(キャノン(株)製)により、365nmにおける照射量が500mJ/cm2の紫外線を全面照射した(フォトブリーチング)。次いで、ホットプレート上において200℃で5分間ポストベークを行い、膜厚600nmの膜を形成した。これらの膜を、アセトン、N-メチルピロリドン、2-プロパノール、及び2-ヘプタノンに、それぞれ23℃にて10分間浸漬した。実施例1乃至実施例4で調製したいずれの感光性樹脂組成物から形成された膜の場合も、上記各溶剤に浸漬前後での膜厚変化が5%以下であることを確認した。
Claims (5)
- (A)成分、(B)成分、(C)成分及び溶剤を含有するマイクロレンズ形成用感光性樹脂組成物。
(A)成分:下記式(1)で表されるマレイミド構造単位、下記式(2)で表されるビニルエーテル構造単位、並びに下記式(3)、式(4)及び式(5)で表される構造単位3種のうち少なくとも1種を有する共重合体
(B)成分:感光剤
(C)成分:架橋剤
- 前記共重合体の重量平均分子量が1000乃至50000である、請求項1又は請求項2に記載のマイクロレンズ形成用感光性樹脂組成物。
- 請求項1乃至請求項3のいずれか一項に記載のマイクロレンズ形成用感光性樹脂組成物から得られる硬化膜。
- 請求項1乃至請求項3のいずれか一項に記載のマイクロレンズ形成用感光性樹脂組成物から作製されるマイクロレンズ。
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US13/982,316 US9052437B2 (en) | 2011-01-31 | 2012-01-12 | Photosensitive resin composition for forming microlens |
JP2012555772A JP5867735B2 (ja) | 2011-01-31 | 2012-01-12 | マイクロレンズ形成用感光性樹脂組成物 |
KR1020137022756A KR101740473B1 (ko) | 2011-01-31 | 2012-01-12 | 마이크로 렌즈 형성용 감광성 수지 조성물 |
CN201280007102.5A CN103339532B (zh) | 2011-01-31 | 2012-01-12 | 微透镜形成用感光性树脂组合物 |
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JP2014189726A (ja) * | 2013-03-28 | 2014-10-06 | Nissan Chem Ind Ltd | レンズ形成用感光性樹脂組成物 |
JP2015132779A (ja) * | 2014-01-15 | 2015-07-23 | 日油株式会社 | 感光性樹脂組成物およびその用途 |
JPWO2015115155A1 (ja) * | 2014-01-30 | 2017-03-23 | 日産化学工業株式会社 | マイクロレンズ形成用樹脂組成物 |
JPWO2015141528A1 (ja) * | 2014-03-20 | 2017-04-06 | 住友ベークライト株式会社 | ポリマー、感光性樹脂組成物および電子装置 |
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KR101987108B1 (ko) * | 2015-03-26 | 2019-06-10 | 동우 화인켐 주식회사 | 착색 감광성 수지 조성물 및 이로부터 제조되는 컬러 필터 |
JP6631871B2 (ja) * | 2015-08-31 | 2020-01-15 | 株式会社リコー | 光加工装置 |
WO2020044918A1 (ja) | 2018-08-30 | 2020-03-05 | 日産化学株式会社 | ネガ型感光性樹脂組成物 |
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- 2012-01-12 WO PCT/JP2012/050479 patent/WO2012105288A1/ja active Application Filing
- 2012-01-12 CN CN201280007102.5A patent/CN103339532B/zh active Active
- 2012-01-12 JP JP2012555772A patent/JP5867735B2/ja active Active
- 2012-01-30 TW TW101102880A patent/TWI557141B/zh active
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JPWO2015141528A1 (ja) * | 2014-03-20 | 2017-04-06 | 住友ベークライト株式会社 | ポリマー、感光性樹脂組成物および電子装置 |
Also Published As
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KR20140006932A (ko) | 2014-01-16 |
US20130310480A1 (en) | 2013-11-21 |
JPWO2012105288A1 (ja) | 2014-07-03 |
US9052437B2 (en) | 2015-06-09 |
TWI557141B (zh) | 2016-11-11 |
KR101740473B1 (ko) | 2017-05-26 |
JP5867735B2 (ja) | 2016-02-24 |
TW201245242A (en) | 2012-11-16 |
CN103339532A (zh) | 2013-10-02 |
CN103339532B (zh) | 2016-06-22 |
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