# US 12,601,970 B2 · Photosensitive resin composition, method for manufacturing patterned cured product, cured product, interlayer insulating film, cover coat layer, surface protective film, and electronic component > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,601,970 B2 - Document ID: US12601970B2 - Status: Granted - Kind: B2 - Application number: 17/282,457 - Filed: 2019-06-17 - Published: 2021-12-09 - Granted: 2026-04-14 - Earliest claimed: 2018-10-03 - Assignees: Hd Microsystems, Ltd. - Applicants: Hd Microsystems, Ltd. - Inventors: Hiroko Yotsuyanagi; Daisaku Matsukawa; Noriyuki Yamazaki - Web page: https://patentgrep.com/patent/US12601970B2 ## CPC - G03F 7/037: the binders being polyamides or polyimides - G03F 7/027: Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds (G03F7/075 takes precedence) - G03F 7/031: Organic compounds not covered by group G03F7/029 - G03F 7/40: Treatment after imagewise removal, e.g. baking - 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; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G) ## Abstract A photosensitive resin composition comprising (A) a polyimide precursor having a polymerizable unsaturated bond; (B) a polymerizable monomer; (C) a photopolymerization initiator; and (D) an ultraviolet absorber. ## Claims ### Claim 1 A photosensitive resin composition comprising: (A) a polyimide precursor having a structural unit represented by the following formula (1); (B) a polymerizable monomer having two or more groups comprising a polymerizable unsaturated double bond; (C) a photopolymerization initiator; and (D) one or more selected from the group consisting of 2,2′,4,4′-tetrahydroxybenzophenone, 2,2′-dihydroxy-4,4′-dimethoxybenzophenone, 4-[ethyl (2-hydroxyethyl)amino]-4′-nitroazobenzene, (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione, and 1,7-bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione: wherein in the formula (1), X1 is a tetravalent group having one or more aromatic groups; a —COOR1 group and a —CONH— group are on the ortho-position to each other; a —COOR2 group and a —CO— group are on the ortho-position to each other; Y1 is a divalent group having one or more aromatic groups; R1 and R2 are independently a hydrogen atom, a group represented by the following formula (2), or an aliphatic hydrocarbon group including 1 to 4 carbon atoms; provided that at least one of R1 and R2 is the group represented by the formula (2): wherein in the formula (2), R3 to R5 are independently a hydrogen atom or an aliphatic hydrocarbon group including 1 to 3 carbon atoms; and m is an integer of 1 to 10. ### Claim 2 (depends on 1) The photosensitive resin composition according to claim 1, wherein the polymerizable monomer has an aliphatic cyclic skeleton. ### Claim 3 (depends on 1) The photosensitive resin composition according to claim 1, wherein the component (B) comprises a polymerizable monomer represented by the following formula (3): wherein in the formula (3), R6 and R7 are independently an aliphatic hydrocarbon group including 1 to 4 carbon atoms, or a group represented by the following formula (4); n1 is 0 or 1; n2 is an integer of 0 to 2; provided that n1+n2 is 1 or more; and at least one of the n1 R6's and the n2 R7's is a group represented by the following formula (4): wherein in the formula (4), R9 to R11 are independently a hydrogen atom, or an aliphatic hydrocarbon group including 1 to 3 carbon atoms; and I is an integer of 0 to 10. ### Claim 4 (depends on 3) The photosensitive resin composition according to claim 3, wherein n1+n2 is 2 or 3. ### Claim 5 (depends on 1) The photosensitive resin composition according to claim 1, wherein the component (B) comprises a polymerizable monomer represented by the following formula (5): ### Claim 6 (depends on 1) The photosensitive resin composition according to claim 1, further comprising (I) a thermal polymerization initiator. ### Claim 7 (depends on 1) The photosensitive resin composition according to claim 1, wherein the component (D) comprises at least (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione. ### Claim 8 (depends on 1) The photosensitive resin composition according to claim 1, wherein Y1 is a divalent group represented by the following formula (7): wherein in the formula (7), R12 to R19 are independently a hydrogen atom, a monovalent aliphatic hydrocarbon group, or a monovalent organic group having a halogen atom. ### Claim 9 (depends on 8) The photosensitive resin composition according to claim 8, wherein R12 to R19 are independently a hydrogen atom, or a monovalent aliphatic hydrocarbon group. ### Claim 10 (depends on 1) The photosensitive resin composition according to claim 1, further comprising (E) a polymerization inhibitor. ### Claim 11 (depends on 1) The photosensitive resin composition according to claim 1, further comprising (H) a sensitizer. ### Claim 12 A photosensitive resin composition comprising: (A) a polyimide precursor having a polymerizable unsaturated bond; (B) a polymerizable monomer; (C) a photopolymerization initiator; and (D) 4-[ethyl (2-hydroxyethyl)amino]-4′-nitroazobenzene. ### Claim 13 A photosensitive resin composition comprising: (A) a polyimide precursor having a polymerizable unsaturated bond; (B) a polymerizable monomer; (C) a photopolymerization initiator; and (D) 1,7-bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione. ### Claim 14 (depends on 1) A method for producing a patterned cured product comprising: applying the photosensitive resin composition according to claim 1 on a substrate, followed by drying to form a photosensitive resin film; pattern-exposing the photosensitive resin film to obtain a resin film; developing the resin film having undergone the pattern exposure using an organic solvent to obtain a patterned resin film; and heat-treating the patterned resin film. ### Claim 15 (depends on 14) The method for producing the patterned cured product according to claim 14, wherein a temperature of the heat treatment is 200° C. or lower. ### Claim 16 (depends on 1) A cured product obtained by curing the photosensitive resin composition according to claim 1. ### Claim 17 (depends on 16) The cured product according to claim 16, which is a patterned cured product. ### Claim 18 (depends on 16) An interlayer insulating film, a cover coat layer, or a surface protective film manufactured by using the cured product according to claim 16. ### Claim 19 (depends on 18) An electronic component comprising the interlayer insulating film, the cover coat layer, or the surface protective film according to claim 18.