WO2022181419A1 - Composition de résine photosensible, objet durci, dispositif d'affichage, dispositif d'affichage électroluminescent organique, et dispositif à semi-conducteurs - Google Patents

Composition de résine photosensible, objet durci, dispositif d'affichage, dispositif d'affichage électroluminescent organique, et dispositif à semi-conducteurs Download PDF

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WO2022181419A1
WO2022181419A1 PCT/JP2022/006162 JP2022006162W WO2022181419A1 WO 2022181419 A1 WO2022181419 A1 WO 2022181419A1 JP 2022006162 W JP2022006162 W JP 2022006162W WO 2022181419 A1 WO2022181419 A1 WO 2022181419A1
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resin composition
photosensitive resin
weight
compound
acid
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PCT/JP2022/006162
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English (en)
Japanese (ja)
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福島航
首藤勇太
原田早葵
亀本聡
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東レ株式会社
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Priority to JP2022510944A priority Critical patent/JPWO2022181419A1/ja
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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
    • 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
    • G03F7/022—Quinonediazides
    • 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
    • G03F7/22—Exposing sequentially with the same light pattern different positions of the same surface
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/10—OLED displays
    • H10K59/12—Active-matrix OLED [AMOLED] displays
    • H10K59/122—Pixel-defining structures or layers, e.g. banks

Definitions

  • the present invention relates to a photosensitive resin composition containing specific ratios and contents of two types of photoacid generators.
  • TFTs thin film transistors
  • a photosensitive resin composition suitable for use as a flattening film for a substrate, a wiring protection insulating film for a circuit board, a flattening film for a solid-state image pickup device, and the like.
  • Photosensitive resin compositions containing polyimide are widely used for surface protective films, interlayer insulating films, planarizing films, etc. of semiconductor elements, and recently, for example, insulating films of organic EL elements, planarizing films of TFT substrates, etc. used for
  • 1,2-naphthoquinone-2-diazide-4-sulfone is disclosed in Patent Documents 1 to 4 as a technique for increasing the sensitivity, increasing the resolution, and rectangularizing the cross section of a positive photosensitive resin composition using a photoacid generator. It is described that the acid ester compound and the 1,2-naphthoquinone-2-diazide-5-sulfonic acid ester compound are mixed in a specific ratio and that the coating film is adjusted to have a specific absorbance.
  • the present invention relates to a positive photosensitive resin composition that uses a photoacid generator, and achieves high sensitivity in broadband exposure including i-line (365 nm), h-line (405 nm) and g-line (436 nm). is the subject.
  • the present invention provides a photosensitive resin composition containing (A) an alkali-soluble resin and (B) a photoacid generator, (B) the photoacid generator comprises (B-1) 1,2-naphthoquinone-2-diazide-4-sulfonic acid ester compound and (B-2) 1,2-naphthoquinone-2-diazide-5-sulfone containing an acid ester compound,
  • the content of compound (B-1) is B1 (weight)
  • the content of compound (B-2) is B2 (weight)
  • the weight ratio B1/B2 is 1.0 ⁇ B1/B2 ⁇ 4.
  • the photosensitive resin composition contains 32 to 55 parts by weight of a photoacid generator (B) with respect to 100 parts by weight of the alkali-soluble resin (A) in the photosensitive resin composition so that the film thickness is 4.0 ⁇ m.
  • a photosensitive resin composition having a transmittance of 30% or more at 436 nm when a coated film of a material is formed.
  • a highly sensitive photosensitive resin composition can be obtained.
  • the photosensitive resin composition of the present invention is a photosensitive resin composition containing (A) an alkali-soluble resin and (B) a photoacid generator, (B) the photoacid generator comprises (B-1) 1,2-naphthoquinone-2-diazide-4-sulfonic acid ester compound and (B-2) 1,2-naphthoquinone-2-diazide-5-sulfone containing an acid ester compound,
  • the content of compound (B-1) is B1 (weight)
  • the content of compound (B-2) is B2 (weight)
  • the weight ratio B1/B2 is 1.0 ⁇ B1/B2 ⁇ 4.
  • the photosensitive resin composition of the present invention contains (A) an alkali-soluble resin (hereinafter sometimes referred to as component (A)).
  • component (A) an alkali-soluble resin
  • the alkali-soluble resin is preferably contained in an amount of 30 to 60% by weight in the photosensitive resin composition from the viewpoint of workability.
  • Alkali solubility means that a solution obtained by dissolving a resin in ⁇ -butyrolactone is coated on a silicon wafer and prebaked at 120° C. for 4 minutes to form a prebaked film having a film thickness of 10 ⁇ m ⁇ 0.5 ⁇ m. It refers to a dissolution rate of 50 nm/min or more, which is obtained from the decrease in film thickness when the film is immersed in a 2.38% by weight tetramethylammonium hydroxide aqueous solution at ⁇ 1° C. for 1 minute and then rinsed with pure water.
  • Component (A) includes polyimides, polyimide precursors, polybenzoxazoles, polybenzoxazole precursors, polyaminoamides, polyamides, polymers obtained from radically polymerizable monomers having alkali-soluble groups, cardo resins, phenolic resins, cyclic Known alkali-soluble resins such as olefin polymers and siloxane resins can be used, but are not limited to these. Two or more of these resins may be contained.
  • the component (A) preferably contains one or more selected from the group consisting of polyimides, polyimide precursors, polybenzoxazoles, polybenzoxazole precursors and copolymers thereof.
  • the component (A) preferably has an acidic group such as a carboxyl group, a phenolic hydroxyl group, or a sulfonic acid group in the structural unit of the component (A) and/or at the main chain end thereof in order to impart alkali solubility. . Further, it preferably contains a fluorine atom, and when developing with an alkaline aqueous solution, it can impart water repellency to the interface between the film and the substrate and suppress the penetration of the alkaline aqueous solution into the interface.
  • an acidic group such as a carboxyl group, a phenolic hydroxyl group, or a sulfonic acid group in the structural unit of the component (A) and/or at the main chain end thereof in order to impart alkali solubility.
  • it preferably contains a fluorine atom, and when developing with an alkaline aqueous solution, it can impart water repellency to the interface between the film and the substrate and suppress the penetration of the alkaline
  • the fluorine atom content with respect to 100 parts by weight of the alkali-soluble resin is preferably 5 parts by weight or more from the viewpoint of the effect of preventing penetration of the alkaline aqueous solution into the interface, and preferably 20 parts by weight or less from the viewpoint of solubility in the alkaline aqueous solution.
  • the polyimide described above has a structural unit represented by formula (9), the polybenzoxazole has a structural unit represented by formula (10), and the polyimide precursor and polybenzoxazole precursor are represented by formula (11) It is preferable to have a structural unit represented by
  • R 25 represents a tetravalent to decavalent organic group having 5 to 60 carbon atoms
  • R 26 represents a divalent to octavalent organic group having 5 to 60 carbon atoms
  • R 27 and R 28 each represent a carboxyl group or a hydroxyl group, each of which may be a single group or a mixture of different groups.
  • p and q represent an integer of 0-6;
  • R 29 represents a di- to octavalent organic group having 5 to 60 carbon atoms
  • R 30 represents a di- to octavalent organic group having 5 to 60 carbon atoms
  • Each R31 independently represents COOR33 .
  • Each R 32 independently represents a hydroxyl group or COOR 33
  • R 33 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms.
  • r and s each independently represent an integer of 0 to 6, where r+s>0.
  • formula (11) represents a structural unit of a polyimide precursor
  • at least two of R 31 are COOR 33 and are present at positions forming an imide ring with an amide bond that bonds to R 29 , and r ⁇ 2 is.
  • formula (11) represents a structural unit of a polybenzoxazole precursor
  • at least two of R 32 are hydroxyl groups, and the hydroxyl groups are present at positions forming an oxazole ring with an amide bond bonding to R 30 , and s ⁇ 2.
  • the component (A) preferably has 5 to 100,000 structural units of one or more types selected from the group consisting of formulas (9) to (11). In addition to the structural units represented by formulas (9) to (11), it may have other structural units. In this case, component (A) preferably contains structural units represented by formulas (9) to (11) in an amount of 50 mol% or more out of 100 mol% of all structural units in component (A).
  • R 25 -(R 27 ) p represents an acid dianhydride residue.
  • R 25 -(R 27 ) p represents a dicarboxylic acid residue.
  • R 25 is a tetravalent to 10-valent organic group having 5 to 60 carbon atoms, preferably an organic group having 5 to 40 carbon atoms and containing an aromatic ring or a cycloaliphatic group.
  • acid dianhydrides include pyromellitic dianhydride, 3,3′,4,4′-biphenyltetracarboxylic dianhydride, and 2,3,3′,4′-biphenyltetracarboxylic acid.
  • R34 represents an oxygen atom, C( CF3 ) 2 , or C( CH3 ) 2 .
  • R35 and R36 represent a hydrogen atom or a hydroxyl group.
  • dicarboxylic acids include terephthalic acid, isophthalic acid, diphenyletherdicarboxylic acid, bis(carboxyphenyl)hexafluoropropane, biphenyldicarboxylic acid, benzophenonedicarboxylic acid, and triphenyldicarboxylic acid. acid, trimesic acid, diphenyl ether tricarboxylic acid, biphenyl tricarboxylic acid, and the like. You may use 2 or more types of these.
  • R 29 -(R 31 ) r represents an acid residue.
  • R 29 is a divalent to octavalent organic group having 5 to 60 carbon atoms, preferably an organic group having 5 to 40 carbon atoms and containing an aromatic ring or a cycloaliphatic group.
  • acid components include dicarboxylic acids such as terephthalic acid, isophthalic acid, diphenyletherdicarboxylic acid, bis(carboxyphenyl)hexafluoropropane, biphenyldicarboxylic acid, benzophenonedicarboxylic acid, and triphenyldicarboxylic acid, and tricarboxylic acids such as trimellit. acid, trimesic acid, diphenyl ether tricarboxylic acid, biphenyltricarboxylic acid, etc.
  • dicarboxylic acids such as terephthalic acid, isophthalic acid, diphenyletherdicarboxylic acid, bis(carboxyphenyl)hexafluoropropane, biphenyldicarboxylic acid, benzophenonedicarboxylic acid, and triphenyldicarboxylic acid
  • tricarboxylic acids such as trimellit. acid, trimesic acid, diphenyl ether
  • tetracarboxylic acids are pyromellitic acid, 3,3′,4,4′-biphenyltetracarboxylic acid, 2,3,3′,4′-biphenyl Tetracarboxylic acid, 2,2',3,3'-biphenyltetracarboxylic acid, 3,3',4,4'-benzophenonetetracarboxylic acid, 2,2',3,3'-benzophenonetetracarboxylic acid, 2 , 2-bis(3,4-dicarboxyphenyl)hexafluoropropane, 2,2-bis(2,3-dicarboxyphenyl)hexafluoropropane, 1,1-bis(3,4-dicarboxyphenyl)ethane , 1,1-bis(2,3-dicarboxyphenyl)ethane, bis(3,4-dicarboxyphenyphenyl)methane, bis(2,3-dicarboxyphenyl)methane,
  • R34 represents an oxygen atom, C( CF3 ) 2 , or C( CH3 ) 2 .
  • R35 and R36 represent a hydrogen atom or a hydroxyl group.
  • one or two carboxyl groups correspond to the R 31 group in formula (11). More preferably, 1 to 4 hydrogen atoms of the above-exemplified dicarboxylic acids, tricarboxylic acids, and tetracarboxylic acids are substituted with R 31 groups, preferably hydroxyl groups, in the formula (11). These acids can be used as they are or as acid anhydrides or active esters.
  • R 26 -(R 28 ) q in formulas (9) and (10) and R 30 -(R 32 ) s in formula (11) represent diamine residues.
  • R 26 and R 30 are divalent to octavalent organic groups having 5 to 60 carbon atoms, and organic groups having 5 to 40 carbon atoms containing an aromatic ring or a cycloaliphatic group are particularly preferred.
  • diamines include 3,4′-diaminodiphenyl ether, 4,4′-diaminodiphenyl ether, 3,4′-diaminodiphenylmethane, 4,4′-diaminodiphenylmethane, 1,4-bis(4-amino phenoxy)benzene, benzidine, m-phenylenediamine, p-phenylenediamine, 1,5-naphthalenediamine, 2,6-naphthalenediamine, bis(4-aminophenoxy)biphenyl, bis ⁇ 4-(4-aminophenoxy)phenyl ⁇ ether, 1,4-bis(4-aminophenoxy)benzene, 2,2′-dimethyl-4,4′-diaminobiphenyl, 2,2′-diethyl-4,4′-diaminobiphenyl, 3,3′ -dimethyl-4,4'-diaminobiphenyl, 3,3
  • R34 represents an oxygen atom, C( CF3 ) 2 , or C( CH3 ) 2 .
  • R 35 to R 38 each independently represent a hydrogen atom or a hydroxyl group.
  • the diamine preferably has a diamine residue represented by formula (8).
  • R 19 to R 22 are each independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a phenyl group, or It represents an alkyl-substituted phenyl group in which at least one hydrogen atom of a phenyl group is substituted with an alkyl group having 1 to 10 carbon atoms.
  • a plurality of R 23 and R 24 may be the same or different.
  • R 23 and R 24 each independently represent an alkylene group having 1 to 5 carbon atoms.
  • m represents an integer of 1-3.
  • the diamine residue represented by formula (8) has a siloxane structure, it can impart high adhesiveness particularly to inorganic materials such as SiN, SiO 2 , Ti, and ITO. From the viewpoint of adhesiveness, it is preferably at least 1 mol % of all diamine residues contained in component (A), and from the viewpoint of photosensitivity, it is preferably at most 20 mol %.
  • alkali-soluble resins by blocking the terminal of these alkali-soluble resins with a monoamine, acid anhydride, acid chloride, or monocarboxylic acid having an acidic group, an alkali-soluble resin having an acidic group at the main chain terminal can be obtained.
  • Preferred examples of such monoamines include 5-amino-8-hydroxyquinoline, 2-aminobenzoic acid, 3-aminobenzoic acid, 4-aminobenzoic acid, 4-aminosalicylic acid, 5-aminosalicylic acid, 6-amino salicylic acid, 3-amino-4,6-dihydroxypyrimidine, 2-aminophenol, 3-aminophenol, 4-aminophenol, 2-aminothiophenol, and the like. You may use 2 or more types of these.
  • acid anhydrides examples include acids such as phthalic anhydride, maleic anhydride, nadic anhydride, cyclohexanedicarboxylic anhydride and 3-hydroxyphthalic anhydride.
  • Monocarboxylic acids such as anhydrides, 3-carboxyphenol and 4-carboxyphenol, monoacid chloride compounds in which the carboxyl groups of these are acid chlorides, dicarboxylic acids such as terephthalic acid, phthalic acid, maleic acid and cyclohexanedicarboxylic acid
  • the content of the terminal blocking agent such as monoamine, acid anhydride, acid chloride, and monocarboxylic acid is 2 to 25 mol% with respect to 100 mol% of the total acid and amine components constituting the alkali-soluble resin. preferable.
  • the component (A) component is synthesized by a known method.
  • the production method includes, for example, a method of reacting a tetracarboxylic dianhydride and a diamine compound at a low temperature, a method of reacting a tetracarboxylic dianhydride and A method of obtaining a diester with an alcohol and then reacting it with an amine in the presence of a condensing agent, a method of obtaining a diester with a tetracarboxylic dianhydride and an alcohol, then converting the remaining dicarboxylic acid into an acid chloride and reacting it with an amine, etc. can be synthesized with
  • the component (A) is a polyhydroxyamide, which is a polybenzoxazole precursor, it can be obtained by a condensation reaction between a bisaminophenol compound and a dicarboxylic acid.
  • a solution of dichloride is added dropwise.
  • the component (A) is a polyimide
  • it can be obtained by dehydrating and ring-closing the polyamic acid or polyamic acid ester obtained by the above method by heating or chemical treatment with an acid or base.
  • polybenzoxazole it can be obtained by dehydrating and ring-closing the polybenzoxazole precursor (polyhydroxyamide) obtained by the above method by heating or chemical treatment with an acid or base.
  • a polymer obtained from a radically polymerizable monomer having an alkali-soluble group uses a radically polymerizable monomer having a phenolic hydroxyl group or a carboxyl group in order to impart alkali solubility.
  • Radical polymerizable monomers having a phenolic hydroxyl group or carboxyl group include, for example, o-hydroxystyrene, m-hydroxystyrene and p-hydroxystyrene, and alkyl, alkoxy, halogen, haloalkyl, nitro, cyano, amide and ester thereof.
  • polyhydroxyvinylphenols such as vinylhydroquinone, 5-vinylpyrogallol, 6-vinylpyrogallol, 1-vinylphlologlycinol; o-vinylbenzoic acid, m-vinylbenzoic acid, and p-vinyl Benzoic acid and alkyl, alkoxy, halogen, nitro, cyano, amide, ester-substituted versions thereof, methacrylic acid and acrylic acid, and haloalkyl, alkoxy, halogen, nitro, cyano-substituted versions thereof in ⁇ -position; maleic acid, Divalent unsaturated carboxylic acids such as maleic anhydride, fumaric acid, fumaric anhydride, citraconic acid, mesaconic acid, itaconic acid and 1,4-cyclohexenedicarboxylic acid, and their methyl, ethyl, propyl,
  • polyhydroxyvinylphenols such as
  • o-hydroxystyrene, m-hydroxystyrene and p-hydroxystyrene, and their alkyl- and alkoxy-substituted products have excellent sensitivity and resolution during patterning, film retention rate after development, heat distortion resistance, solvent resistance, It is preferably used from the viewpoint of adhesion to the substrate, storage stability of the solution, and the like. These can be used together with one or two or more monomers.
  • radically polymerizable monomers can be used for the polymer obtained from the radically polymerizable monomer having an alkali-soluble group.
  • Other radically polymerizable monomers are, for example, styrene and ⁇ -, o-, m- or p-position alkyl, alkoxy, halogen, haloalkyl, nitro, cyano, amide, ester substituents of styrene; , isoprene, chloroprene, etc.; methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, ter-butyl, pentyl, neopentyl, isoamylhexyl, cyclohexyl, adamantyl of methacrylic acid or acrylic acid , allyl, propargyl, phenyl, naphthyl, anthracenyl, anth
  • the preferred proportion of the other radically polymerizable monomer is the radically polymerizable monomer having a phenolic hydroxyl group and the other radically polymerizable monomer. It is preferably 40 parts by weight or less, particularly preferably 5 to 30 parts by weight, based on 100 parts by weight of the radically polymerizable monomers.
  • the preferred proportion of the other radically polymerizable monomer is the radically polymerizable monomer having a carboxyl group and the other radically polymerizable monomer. It is preferably 90 parts by weight or less, particularly preferably 10 to 80 parts by weight, based on 100 parts by weight of the radically polymerizable monomers. Alkaline development is facilitated when the proportion of these other radically polymerizable monomers is within the range described above with respect to the radically polymerizable monomer having a phenolic hydroxyl group or a carboxyl group, which is preferable.
  • Solvents used in the production of polymers obtained from radically polymerizable monomers having an alkali-soluble group include, for example, alcohols such as methanol and ethanol; ethers such as tetrahydrofuran; glycols such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether.
  • ethylene glycol alkyl ether acetates such as methyl cellosolve acetate and ethyl cellosolve acetate
  • diethylene glycols such as diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether and diethylene glycol ethyl methyl ether
  • propylene glycol monomethyl ether, propylene propylene glycol monoalkyl ethers such as glycol monoethyl ether
  • propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, propylene glycol propyl ether acetate, propylene glycol butyl ether acetate
  • Propylene glycol alkyl ether propionates such as pionate, propylene glycol e
  • Polymerization initiators used for producing polymers obtained from radically polymerizable monomers having an alkali-soluble group include, for example, 2,2′-azobisisobutyronitrile, 2,2′-azobis-(2,4-dimethyl valeronitrile), azo compounds such as 2,2'-azobis-(4-methoxy-2,4-dimethylvaleronitrile); benzoyl peroxide, lauroyl peroxide, t-butyl peroxypivalate, 1,1'-bis- organic peroxides such as (t-butylperoxy)cyclohexane; and hydrogen peroxide.
  • the peroxide may be used together with a reducing agent as a redox initiator.
  • a preferred weight average molecular weight of the polymer obtained from the radically polymerizable monomer having an alkali-soluble group is preferably 2000 to 100000, more preferably 3000 to 50000, particularly preferably 5000 to 5000, in terms of polystyrene using gel permeation chromatography. 30000. If the weight-average molecular weight exceeds 100,000, the developability and sensitivity tend to deteriorate, and if it is less than 2,000, the pattern shape, resolution, developability, and heat resistance tend to deteriorate.
  • the polymers obtained from radically polymerizable monomers having these alkali-soluble groups may be used alone or in combination of two or more.
  • an alkali-soluble resin may be synthesized by a method of introducing a protecting group into a carboxyl group or a phenolic hydroxyl group before polymerization and deprotecting it after polymerization to impart alkali solubility. Further, the transparency and softening point in visible light may be changed by hydrogenation treatment or the like.
  • alkali-soluble resins known ones such as cardo resin, phenol resin, cyclic olefin polymer, and siloxane resin can be used.
  • the photosensitive resin composition of the present invention contains (B) a photoacid generator.
  • (B) a photoacid generator By containing a photoacid generator, an acid is generated in the light-irradiated area and the solubility of the light-irradiated area in an alkaline aqueous solution increases, so that a positive relief pattern in which the light-irradiated area dissolves can be obtained. can.
  • (B) by containing a photoacid generator and an epoxy compound or a thermal cross-linking agent described later the acid generated in the light-irradiated portion accelerates the cross-linking reaction of the epoxy compound and the thermal cross-linking agent, and the light-irradiated portion becomes insoluble. A negative relief pattern can be obtained.
  • Photoacid generators include quinonediazide compounds, sulfonium salts, phosphonium salts, diazonium salts, and iodonium salts.
  • a wavelength in the wavelength range of 350 nm to 450 nm, particularly a broadband including g-line (436 nm), h-line (405 nm) and i-line (365 nm) is mainly used. Broadband may also include other wavelengths.
  • the photoacid generator includes (B-1) 1,2-naphthoquinone-2-diazide-4-sulfonic acid ester compound and (B-2) 1,2-naphthoquinone-2-diazide- A 5-sulfonic acid ester compound is contained, and when the content of compound (B-1) is B1 (weight) and the content of compound (B-2) is B2 (weight), the weight ratio B1/B2 is 1.0 ⁇ B1/B2 ⁇ 4.0, and 32 to 55 parts by weight of (B) photoacid generator per 100 parts by weight of (A) alkali-soluble resin in the photosensitive resin composition is required.
  • (B-2) 1,2-naphthoquinone-2-diazide-5-sulfonic acid ester compound reacts with the g-line, so when the compounds (B-1) and (B-2) are used alone, Efficient photosensitivity was not possible with broadband exposure covering all regions of g-line, h-line and i-line.
  • (B-1) 1,2-naphthoquinone-2-diazide-4-sulfonic acid ester compound is colored when reacted with i-line, so that light does not pass to the bottom, and the solubility in alkaline aqueous solution of the light-irradiated part did not increase.
  • the present inventors focused on the absorbance at each wavelength of the photo-acid generator, and (B-2) 1,2-naphthoquinone-2-diazide-5-sulfonic acid ester compound was irradiated with g-rays and reacted, the photobleaching effect increased the transmittance of the i-rays. Then, by setting each of the (B-1) compound and the (B-2) compound to a specific mixing ratio, the (B-1) 1,2-naphthoquinone-2-diazide-4-sulfonic acid ester compound reaches the bottom. In response, the present inventors were able to achieve higher sensitivity than expected.
  • (B-2) 1,2-naphthoquinone-2-diazide-5-sulfonic acid ester compound is also reacted to the bottom, and the photobleaching effect increases i-line transmittance.
  • the transmittance at 436 nm when a coating film of the photosensitive resin composition is formed on the substrate is 30% or more, and particularly preferably 99% or less.
  • 1,2-naphthoquinone-2-diazide-4-sulfonic acid which has a low transmittance at 436 nm, is required to increase the transmittance at 436 nm to 30% or more in a coated film of a photosensitive resin composition having a thickness of 4.0 ⁇ m.
  • the transmittance at 436 nm can be improved.
  • component (B) it is preferable to adjust the 1,2-naphthoquinone-2-diazide-4-sulfonic acid ester compound in the range of less than 80% by weight.
  • the content of the 1,2-naphthoquinone-2-diazide-4-sulfonic acid ester compound is less than 50% by weight, the sensitivity also decreases. It is preferable to adjust the amount in the range of 80% by weight or more.
  • the compound (B-1) preferably contains a compound represented by formula (1), and the compound (B-2) contains a compound represented by formula (2).
  • the compound (B-1) contains a compound represented by the formula (1), and the compound (B-2) contains a compound represented by the formula (2).
  • the photosensitizer generates an acid upon exposure to light, increases its dissolution rate in an alkaline aqueous solution, and makes the system alkali-soluble, thereby effectively improving sensitivity.
  • the (B-1) compound is a mixture of ester substituents and -OH substituents. If the esterification rate is high, there is a problem that the solubility in an alkaline aqueous solution does not increase. On the other hand, when the ester ratio is low, the amount of acid generated when exposed to light is small, and the dissolution rate in an alkaline aqueous solution is insufficient, making it impossible to efficiently improve the sensitivity. Therefore, it is preferable that the compound (B-1) contains the compound represented by the formula (1) and the esterification rate of the compound represented by the formula (1) is 65 mol % to 85 mol %.
  • Specific examples of the compound represented by formula (1) include 4CPA-15, 4CPA-20, 4CAPA-80 (trade names, manufactured by Daito Chemix Co., Ltd.) TP4-250, HA4-170 (trade names, Toyo Gosei Co., Ltd.) and the like.
  • specific examples of the compound represented by formula (2) include TP5-250, TP5-280, and HA5-170 (all trade names, manufactured by Toyo Gosei Co., Ltd.) STP-525 and STP-528 (all trade names). (manufactured by Sambo Kagaku Kenkyusho Co., Ltd.).
  • the photosensitive resin composition of the present invention preferably contains a low-molecular-weight phenol compound.
  • (C) a low-molecular-weight phenol compound the alkali developability of the photosensitive resin composition can be supplemented, and the sensitivity can be improved.
  • the dissolution accelerator is preferably a compound having a phenolic hydroxyl group.
  • the content of the low-molecular-weight phenol compound is preferably 20 to 30 parts by weight with respect to 100 parts by weight of the (A) alkali-soluble resin.
  • the (C) low-molecular-weight phenol compound is contained in an amount of 20 parts by weight or more relative to 100 parts by weight of the alkali-soluble resin (A), the alkali developability can be improved, and the sensitivity can be improved.
  • the (C) low-molecular-weight phenolic compound is contained in an amount of 30 parts by weight or less per 100 parts by weight of the alkali-soluble resin (A), the adhesion between the phenol group and the underlying substrate during development does not become excessive, and the film should be removed. Sensitivity can be improved by being able to remove the film in place.
  • the photosensitive resin composition of the present invention preferably contains (D) a solvent. Thereby, the photosensitive resin composition can be made into a varnish state, and the coatability can be improved.
  • Solvents include polar aprotic solvents such as ⁇ -butyrolactone, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, Diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n- Propyl ether, propylene glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol mono-n-butyl ether, diprop
  • the content of (D) the solvent is not particularly limited, but is preferably 100 to 3000 parts by weight, more preferably 300 to 2000 parts by weight, relative to 100 parts by weight of the alkali-soluble resin (A).
  • the solid content concentration of the photosensitive resin composition is preferably 5% or more and less than 30%, more preferably less than 20%.
  • solid content refers to the entire components of the photosensitive resin composition excluding the organic solvent.
  • the photosensitive resin composition of the present invention can further contain a thermal cross-linking agent.
  • a thermal cross-linking agent refers to a compound having at least two thermally reactive functional groups such as an alkoxymethyl group, a methylol group, an epoxy group, and an oxetanyl group in the molecule.
  • the thermal cross-linking agent cross-links (A) the alkali-soluble resin or other additive components, and can enhance the heat resistance, chemical resistance and hardness of the film after thermal curing.
  • Preferred examples of compounds having at least two alkoxymethyl groups or methylol groups include DML-PC, DML-PEP, DMO-PC, TriML-P, TriML-35XL, TML-HQ, TML-BP, TML- pp-BPF, TML-BPE, TMOM-BP, TMOM-BPE, TMOM-BPA, TMOM-BPAF, TMOM-BPAP, HML-TPPHBA, HML-TPHAP, HMOM-TPPHBA, HMOM-TPHAP (product names, Honshu Chemical Industry Co., Ltd.), NIKALAC (registered trademark) MX-290, NIKALAC MX-280, NIKALAC MX-270, NIKALAC MW-100LM, NIKALAC MX-750LM (product names, manufactured by Sanwa Chemical Co., Ltd.) are available from each of the companies mentioned above.
  • those having two epoxy groups in one molecule include “Epikote” (registered trademark) 807, “Epicote” 828, “Epikote” 1002, “Epicote” 1750, and “Epicote”.
  • VG3101L (trade name, manufactured by Printec Co., Ltd.), “Tepic” (registered trademark) S, “Tepic” G, “Tepic” P (trade names, Nissan Chemical Kogyo Co., Ltd.), "Epiclone” N660, “Epiclone” N695, HP7200 (trade names, manufactured by Dainippon Ink and Chemicals Co., Ltd.), “Denacol” EX-321L (trade name, Nagase ChemteX Corporation) ), NC6000, EPPN502H, NC3000 (trade names, manufactured by Nippon Kayaku Co., Ltd.), “Epotato” (registered trademark) YH-434L (trade name, manufactured by Tohto Kasei Co., Ltd.), EHPE-3150 (trade name , manufactured by Daicel Co., Ltd.), and compounds having two or more oxetanyl groups include OXT-121, OXT-221,
  • the content of the thermal cross-linking agent is preferably 5 parts by weight or more with respect to 100 parts by weight of the (A) alkali-soluble resin, since the cross-linking density is increased and the chemical resistance is improved. Furthermore, when it is 10 parts by weight or more, higher mechanical properties can be obtained. On the other hand, from the viewpoint of the storage stability and mechanical strength of the composition, it is preferably 50 parts by weight or less, more preferably 40 parts by weight or less, and even more preferably 30 parts by weight or less.
  • the photosensitive resin composition of the present invention may contain an adhesion improver, which can assist adhesion after development and improve adhesion after curing.
  • Adhesion improvers include vinyltrimethoxysilane, vinyltriethoxysilane, epoxycyclohexylethyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, p-styryltrimethoxysilane, Silane coupling agents such as 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, titanium chelating agents, aluminum chelating agents, aromatic amine compounds and alkoxy group-containing Examples thereof include compounds obtained by reacting silicon compounds. You may contain 2 or more types of these.
  • the photosensitive resin composition of the present invention may contain a surfactant to improve wettability with the substrate.
  • Surfactants include Florard (trade name, manufactured by Sumitomo 3M Co., Ltd.), “Megafac” (registered trademark) (trade name, manufactured by DIC Corporation), and “Surflon” (trade name, AGC). Seimi Chemical Co., Ltd.), KP341 (trade name, Shin-Etsu Chemical Co., Ltd.), DBE (trade name, Chisso Co., Ltd.), Granol (trade name, Kyoeisha Chemical Co., Ltd.) ), organic siloxane surfactants such as BYK (manufactured by BYK Chemie Co., Ltd.), acrylic polymer surfactants such as Polyflow (trade name, manufactured by Kyoeisha Chemical Co., Ltd.), and the like.
  • ⁇ Coating film coated with photosensitive resin composition> A coating film coated with the photosensitive resin composition of the present invention will be described.
  • the coating film refers to a state in which the photosensitive resin composition is applied and part of the solvent is removed. It is preferable to remove 99% by weight or more of the solvent contained in the photosensitive resin composition.
  • Examples of methods for applying the photosensitive resin composition to the substrate include known methods such as spin coating, slit coating, dip coating, spray coating, and printing.
  • the substrate is not particularly limited as long as a coating film of a photosensitive resin composition can be formed so as to have a thickness of 4.0 ⁇ m and the transmittance at 436 nm can be measured. etc. is preferably used.
  • Methods for removing the solvent include known methods such as vacuum drying and heat drying. In the case of vacuum drying, it is preferable to remove the solvent until the final ultimate pressure reaches 10 Pa to 100 Pa. When drying by heating, the heating temperature is preferably 80°C to 130°C, more preferably 90°C to 120°C. The heating time may be adjusted in the range of 1 minute to several hours.
  • Heat drying and vacuum drying may be used in combination.
  • the heating is preferably from 25°C to 100°C, more preferably from 25°C to 70°C, and the solvent is preferably removed until the final ultimate pressure reaches 10Pa to 100Pa.
  • the coated film of the photosensitive resin composition is used as it is.
  • the cured product of the present invention is a cured product obtained by curing the photosensitive resin composition of the present invention.
  • the cured product can be obtained by curing the photosensitive resin composition by a known heat treatment method or the like.
  • the heating temperature is preferably from 150°C to 400°C, more preferably from 200°C to 350°C.
  • the time is preferably 30 minutes or more and 90 minutes or less, more preferably 45 minutes or more and 60 minutes.
  • a photosensitive resin composition is applied to a substrate by a spin coating method, a slit coating method, a dip coating method, a spray coating method, a printing method, or the like.
  • Silicon wafers sapphire (Al 2 O 3 ), silicon oxide (SiO 2 ), silicon nitride (SiN), gallium nitride (GaN), silicon carbide (SiC), gallium arsenide (GaAs), indium phosphide ( InP), or aluminum nitride (AlN) wafers, substrates having these formed on the coating surface, and the like are used, but are not limited to these.
  • These substrates may be pretreated in advance with the above-mentioned (c) phosphoric acid compound or adhesion improver.
  • Methods for treating the substrate surface include spin coating, slit die coating, bar coating, dip coating, spray coating, vapor treatment, and the like. After applying the photosensitive resin composition, if necessary, it is subjected to reduced pressure drying treatment, and then, using a hot plate, oven, infrared rays, etc., heat treatment is performed at 50 ° C. to 180 ° C. for 1 minute to several hours. to obtain a coating film.
  • the photosensitive resin coating film is irradiated with actinic rays through a mask having a desired pattern.
  • Actinic rays used for exposure include ultraviolet rays, visible rays, electron beams, X-rays, etc.
  • Developers include tetramethylammonium hydroxide, diethanolamine, diethylaminoethanol, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, triethylamine, diethylamine, methylamine, dimethylamine, dimethylaminoethyl acetate, dimethylaminoethanol, dimethyl
  • alkaline compounds such as aminoethyl methacrylate, cyclohexylamine, ethylenediamine and hexamethylenediamine are preferred.
  • these alkaline aqueous solutions may be added with polar solvents such as N-methyl-2-pyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, ⁇ -butyrolactone, dimethylacrylamide, methanol, ethanol, Alcohols such as isopropanol, esters such as ethyl lactate and propylene glycol monomethyl ether acetate, and ketones such as cyclopentanone, cyclohexanone, isobutyl ketone and methyl isobutyl ketone may be added alone or in combination. good.
  • polar solvents such as N-methyl-2-pyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, ⁇ -butyrolactone, dimethylacrylamide, methanol, ethanol, Alcohols such as isopropanol, esters such as ethyl lactate
  • alcohols such as ethanol and isopropyl alcohol
  • esters such as ethyl lactate and propylene glycol monomethyl ether acetate may be added to the distilled water for rinsing.
  • heat treatment is performed to obtain a cured product.
  • Heat treatment can remove residual solvents and components with low heat resistance, so that heat resistance and chemical resistance can be improved.
  • the photosensitive resin composition contains structural units of polyimide precursors and polybenzoxazole precursors, imide rings and oxazole rings can be formed by heat treatment, so heat resistance and chemical resistance can be improved. can.
  • the heat treatment can promote the reaction of thermal cross-linking, thereby improving the heat resistance and chemical resistance.
  • a certain temperature is selected and the temperature is raised stepwise, or a certain temperature range is selected and the temperature is raised continuously for 5 minutes to 5 hours.
  • heat treatment is performed at 150° C. and 250° C. for 30 minutes each.
  • a method of linearly raising the temperature from room temperature to 300° C. over 2 hours can be used.
  • the heat treatment conditions in the present invention are preferably from 150°C to 400°C, more preferably from 200°C to 350°C.
  • the electronic component of the present invention comprises the cured product of the present invention.
  • the display device of the present invention comprises the cured product of the present invention.
  • electronic parts and display devices specifically, electronic parts provided with a cured film as a surface protective film or interlayer insulating film of semiconductor elements such as LSI (Large Scale Integration), insulating films, pixel division layers, and TFT substrates.
  • a display device such as an organic EL display device containing a cured product as the flattening film can be mentioned.
  • an organic EL display device in which the cured film of the present invention is contained in the pixel dividing layer is preferable.
  • the semiconductor device of the present invention comprises the cured product of the present invention. Specifically, it is a semiconductor device containing the cured product of the present invention in the insulating film and/or protective film in the structure of a known semiconductor device.
  • a cured product obtained by curing the photosensitive resin composition of the present invention is excellent in flattening property and pattern dimensional stability, and is therefore preferable for the above insulating film and/or protective film.
  • each film was exposed in steps of 20 mJ/cm 2 at an exposure amount of 0 to 100 mJ/cm 2 .
  • Line & space (L&S) patterns used for exposure are 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, 30, 50 and 100 ⁇ m.
  • TMAH tetramethylammonium aqueous solution
  • the resulting pattern was observed using an FDP microscope MX61 (manufactured by Olympus Corporation) at a magnification of 20 times, and the minimum exposure dose at which a 20 ⁇ m line & space (L/S) pattern was formed at a ratio of 1:1 was measured. and Sensitivity of 60 mJ/cm 2 or more was rated C, sensitivity of 50 mJ/cm 2 or more to less than 60 mJ/cm 2 was rated B, and sensitivity of less than 50 mJ/cm 2 was rated A.
  • the transmission spectrum at a wavelength of 436 nm was measured using an ultraviolet-visible spectrophotometer MultiSpec-1500 (manufactured by Shimadzu Corporation).
  • the coating film was not 4.0 ⁇ m thick, the light transmittance was converted into the light transmittance when the film thickness was 4.0 ⁇ m using the Beer-Lambert law.
  • Synthesis Example 2 Synthesis of alkali-soluble resin (A-1) 3,3',4,4'-diphenyl ether tetracarboxylic dianhydride (hereinafter referred to as ODPA) 31.0 g (0.10 mol) was dissolved in 500 g of N-methyl-2-pyrrolidone (hereinafter NMP). 45.35 g (0.08 mol) of the hydroxyl group-containing diamine compound obtained in Synthesis Example 1 was added together with 50 g of NMP, and reacted at 20°C for 1 hour and then at 50°C for 2 hours.
  • A-1 3,3',4,4'-diphenyl ether tetracarboxylic dianhydride
  • NMP N-methyl-2-pyrrolidone
  • Example 1 10.0 g of the alkali-soluble resin (A-1) obtained in Synthesis Example 2, 2.4 g of the quinonediazide compound (b-1) obtained in Synthesis Example 7, and the quinonediazide compound (b-1) obtained in Synthesis Example 8 ( b-2) 0.8 g and 2.5 g of TrisP-HAP (trade name, manufactured by Honshu Kagaku Kogyo Co., Ltd.) were added and dissolved by adding 30.0 g of propylene glycol monomethyl ether and 8.0 g of GBL as solvents.
  • a photosensitive resin composition (varnish) was obtained by filtering through a 2 ⁇ m polytetrafluoroethylene filter (manufactured by Sumitomo Electric Industries, Ltd.). Using this varnish, sensitivity and transmittance were evaluated by the methods described above. An 8-inch silicon wafer with SiN was used as a substrate for evaluating sensitivity. The evaluation results are shown in Table 1.
  • Example 2 A varnish was obtained in the same manner as in Example 1 with the types and amounts of the compounds listed in Table 1. Using this varnish, sensitivity and transmittance were evaluated in the same manner as in Example 1. Table 1 shows the evaluation results.
  • Example 7 Pigment Yellow 150 (also called PY150) (trade name: E4GNGT, manufactured by Lanxess) was used in the same manner as in Example 1 except that 0.15 was used. A varnish was obtained as described. Sensitivity and transmittance were evaluated in the same manner as in Example 1. Table 2 shows the evaluation results.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Theoretical Computer Science (AREA)
  • Materials For Photolithography (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention a pour objet de fournir une composition de résine photosensible présentant une grande sensibilité. Plus précisément, l'invention concerne une composition de résine photosensible qui comprend une résine soluble dans les alcalis (A) et un générateur de photoacide (B). Lequel générateur de photoacide (B) comprend un composé (B-1) ester d'acide sulfonique １，２－naphthoquinone－２－diazido－４－ et un composé (B-2) ester d'acide sulfonique １，２－naphthoquinone－２－diazido－５－. Lorsque la teneur en composé (B-1) est représentée par Ｂ１ (en masse) et la la teneur en composé (B-2) est représentée par Ｂ2 (en masse), alors le rapport massique (Ｂ１／Ｂ２) est tel que １,０≦Ｂ１／Ｂ２≦４,０. La composition de résine photosensible de l'invention comprend ３２ à ５５ parties en masse du générateur de photoacide (B) pour 100 parties en masse de la résine soluble dans les alcalis (A). Dans le cas où un film de revêtement de cette composition de résine photosensible est formé de manière à présenter une épaisseur de film de ４,０μｍ, sa transmittance pour 346nm est supérieure ou égale à 30%.
PCT/JP2022/006162 2021-02-26 2022-02-16 Composition de résine photosensible, objet durci, dispositif d'affichage, dispositif d'affichage électroluminescent organique, et dispositif à semi-conducteurs WO2022181419A1 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024048270A1 (fr) * 2022-09-02 2024-03-07 Jsr株式会社 Procédé de fabrication d'un film conducteur, dispersion liquide, composition de résine sensible au rayonnement et élément électroluminescent

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008268788A (ja) * 2007-04-25 2008-11-06 Toray Ind Inc 感光性樹脂組成物
JP2009020246A (ja) * 2007-07-11 2009-01-29 Toray Ind Inc 感光性樹脂組成物、これを用いた絶縁性樹脂パターンの製造方法および有機電界発光素子
WO2010134207A1 (fr) * 2009-05-20 2010-11-25 住友ベークライト株式会社 Composite de résine photosensible positive, film de durcissement, film protecteur, film d'isolation de couche intermédiaire, dispositif semi-conducteur et élément d'affichage
JP2014500851A (ja) * 2010-09-28 2014-01-16 プロメラス， エルエルシー ノルボルナンベースのｐａｃバラスト、及びｐａｃを含むポジティブ型の感光性樹脂組成物
JP2016158863A (ja) * 2015-03-02 2016-09-05 株式会社日立製作所 医用画像撮像装置及び撮像断面調整方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008268788A (ja) * 2007-04-25 2008-11-06 Toray Ind Inc 感光性樹脂組成物
JP2009020246A (ja) * 2007-07-11 2009-01-29 Toray Ind Inc 感光性樹脂組成物、これを用いた絶縁性樹脂パターンの製造方法および有機電界発光素子
WO2010134207A1 (fr) * 2009-05-20 2010-11-25 住友ベークライト株式会社 Composite de résine photosensible positive, film de durcissement, film protecteur, film d'isolation de couche intermédiaire, dispositif semi-conducteur et élément d'affichage
JP2014500851A (ja) * 2010-09-28 2014-01-16 プロメラス， エルエルシー ノルボルナンベースのｐａｃバラスト、及びｐａｃを含むポジティブ型の感光性樹脂組成物
JP2016158863A (ja) * 2015-03-02 2016-09-05 株式会社日立製作所 医用画像撮像装置及び撮像断面調整方法

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024048270A1 (fr) * 2022-09-02 2024-03-07 Jsr株式会社 Procédé de fabrication d'un film conducteur, dispersion liquide, composition de résine sensible au rayonnement et élément électroluminescent

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