# US 2021/0278765 A1 · Resist composition and method for producing resist pattern, and method for producing plated molded article > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2021/0278765 A1 - Document ID: US20210278765A1 - Status: Published application - Kind: A1 - Application number: 17/178,794 - Filed: 2021-02-18 - Published: 2021-09-09 - Earliest claimed: 2020-02-21 - Assignees: Sumitomo Chemical Company, Limited - Applicants: Sumitomo Chemical Company, Limited - Inventors: Masako SUGIHARA; Takashi NISHIMURA; Junji NAKANISHI - Web page: https://patentgrep.com/patent/US20210278765A1 ## CPC - G03F 7/0233: {characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides} - C08F 212/22: {Oxygen} - C08F 212/24: {Phenols or alcohols} - C09D 125/18: Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen - G03F 7/022: Quinonediazides (G03F7/075 takes precedence) - G03F 7/0236: {Condensation products of carbonyl compounds and phenolic compounds, e.g. novolak resins} - G03F 7/038: Macromolecular compounds which are rendered insoluble or differentially wettable (G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021) - G03F 7/039: Macromolecular compounds which are photodegradable, e.g. positive electron resists (G03F7/075 takes precedence; macromolecular quinonediazides G03F7/023) - G03F 7/0392: {the macromolecular compound being present in a chemically amplified positive photoresist composition} - G03F 7/0397: {the macromolecular compound having an alicyclic moiety in a side chain} - G03F 7/30: Imagewise removal using liquid means - 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) - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D) ## Abstract The present invention provides a resist composition which has sufficient resistant to a plating treatment and is capable of forming a resist pattern with high accuracy. The present invention also provides a method for producing a resist pattern using the resist composition, and a method for producing a plated molded article using the resist pattern. The present invention relates to a resist composition comprising a compound (I) having a quinone diazide sulfonyl group, a resin comprising a structural unit having an acid-labile group (A1), an alkali-soluble resin (A2) and an acid generator (B); a method for producing a resist pattern using the resist composition; and a method for producing a plated molded article using the resist pattern. ## Claims ### Claim 1 A resist composition comprising a compound (I) having a quinone diazide sulfonyl group, a resin comprising a structural unit having an acid-labile group (A1), an alkali-soluble resin (A2) and an acid generator (B). ### Claim 2 (depends on 1) The resist composition according to claim 1, wherein the compound (I) having a quinone diazide sulfonyl group is a compound having a group represented by formula (a), a group represented by formula (b) or a group represented by formula (c): wherein, in formula (a) and formula (b), * represents a bond: wherein, in formula (c), * represents a bond. ### Claim 3 (depends on 2) The resist composition according to claim 2, wherein the compound (I) having a quinone diazide sulfonyl group is at least one selected from the group consisting of a compound represented by formula (II), a compound represented by formula (III), a compound represented by formula (IV) and a compound represented by formula (V): wherein, in formula (II), R11 to R14 each independently represent a hydrogen atom, a hydroxy group, a hydrocarbon group having 1 to 18 carbon atoms, a group represented by formula (a), a group represented by formula (b) or a group represented by formula (c), and a methylene group included in the hydrocarbon group having 1 to 18 carbon atoms may be replaced by an oxygen atom, a carbonyl group or —NRd1—, Rd1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R15 to R30 each independently represent a hydrogen atom, a hydroxy group, a group represented by formula (a), a group represented by formula (b) or a group represented by formula (c), and at least one of R11 to R30 is a group represented by formula (a), a group represented by formula (b) or a group represented by formula (c): wherein, in formula (III), R31 to R39 each independently represent a hydrogen atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, a group represented by formula (a), a group represented by formula (b) or a group represented by formula (c), and at least one of R31 to R39 is a group represented by formula (a), a group represented by formula (b) or a group represented by formula (c), P1 to P5 each independently represent a hydrogen atom, a hydrocarbon group having 1 to 18 carbon atoms, a methylene group included in the hydrocarbon group having 1 to 18 carbon atoms may be replaced by an oxygen atom, a carbonyl group or —NRd2—, and P1 and P2 may be bonded to each other to form a ring together with two carbon atoms to which P1 and P2 are bonded, and P4 and P3 may be bonded to each other to form a ring together with carbon atoms to which P4 and P3 are bonded, and Rd2 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms: wherein, in formula (IV), R40 to R53 each independently represent a hydrogen atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, a group represented by formula (a), a group represented by formula (b) or a group represented by formula (c), and at least one of R40 to R53 is a group represented by formula (a), a group represented by formula (b) or a group represented by formula (c), and na represents an integer of 1 to 5, and when na is an integer of 2 or more, a plurality of R49 to R52 may be the same or different from each other: wherein, in formula (V), Rf1, Rf2 and Rg1 to Rg8 each independently represent a hydrogen atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, a group represented by formula (a), a group represented by formula (b) or a group represented by formula (c), and at least one of Rf1, Rf2 and Rg1 to Rg8 is a group represented by formula (a), a group represented by formula (b) or a group represented by formula (c), P6 represents a monovalent aromatic hydrocarbon group having 6 to 12 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 12 carbon atoms, and the aromatic hydrocarbon group may be substituted with at least one selected from the group consisting of a hydroxy group and an alkyl group having 1 to 6 carbon atoms, P7 represents a hydrogen atom or a hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, a methylene group included in the hydrocarbon group having 1 to 18 carbon atoms may be replaced by an oxygen atom, a carbonyl group or —NRd3-, and P6 and P7 may be bonded to each other to form a ring, nv represents 1 or 2, and Rd3 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. ### Claim 4 (depends on 1) The resist composition according to claim 1, wherein the resin comprising a structural unit having an acid-labile group (A1) is a resin comprising a structural unit having a group represented by formula (10) or a group represented by formula (20): wherein, in formula (10), Ra1, Ra2 and Ra3 each independently represent an alkyl group having 1 to 8 carbon atoms or an alicyclic hydrocarbon group having 3 to 20 carbon atoms, or Ra1 and Ra2 are bonded to each other to form a ring having 3 to 20 carbon atoms together with carbon atoms to which Ra1 and Ra2 are bonded, and Ra3 represents an alkyl group having 1 to 8 carbon atoms or an alicyclic hydrocarbon group having 3 to 20 carbon atoms, ma and na each independently represent 0 or 1, at least one of ma and na represents 1, and * represents a bond: wherein, in formula (20), Ra1′ and Ra2′ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, Ra3′ represents a hydrocarbon group having 1 to 20 carbon atoms, or Ra1′ represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and Ra2′ and Ra3′ are bonded to each other to form an heterocyclic ring having 3 to 20 carbon atoms together with carbon atoms and X to which Ra2′ and Ra3′ are bonded, a methylene group included in the hydrocarbon group having 1 to 20 carbon atoms and the heterocyclic ring having 3 to 20 carbon atoms may be replaced by an oxygen atom or a sulfur atom, X represents an oxygen atom or a sulfur atom, na′ represents 0 or 1, and * represents a bond. ### Claim 5 (depends on 1) The resist composition according to claim 1, wherein the resin comprising a structural unit having an acid-labile group (A1) is a resin comprising a structural unit represented by formula (a1-1) or a structural unit represented by formula (a1-2): wherein, in formula (a1-1), Ra1, Ra2 and Ra3 each independently represent an alkyl group having 1 to 8 carbon atoms or an alicyclic hydrocarbon group having 3 to 20 carbon atoms, or Ra1 and Ra2 are bonded to each other to form a ring having 3 to 20 carbon atoms together with carbon atoms to which Ra1 and Ra2 are bonded, and Ra3 represents an alkyl group having 1 to 8 carbon atoms or an alicyclic hydrocarbon group having 3 to 20 carbon atoms, and Ra4 represents a hydrogen atom or a methyl group: wherein, in formula (a1-2), Ra1′ and Ra2′ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, Ra3′ represents a hydrocarbon group having 1 to 20 carbon atoms, or Ra1′ represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and Ra2′ and Ra3′ are bonded to each other to form an heterocyclic ring having 3 to 20 carbon atoms together with carbon atoms and oxygen atoms to which Ra2′ and Ra3′ are bonded, and a methylene group included in the hydrocarbon group having 1 to 20 carbon atoms and the heterocyclic ring having 3 to 20 carbon atoms may be replaced by an oxygen atom or a sulfur atom, Ra5 represents a hydrogen atom or a methyl group, Ra6 represents an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, and m represents an integer of 0 to 4, and when m is 2 or more, a plurality of Ra6 may be the same or different from each other. ### Claim 6 (depends on 1) The resist composition according to claim 1, wherein the resin comprising a structural unit having an acid-labile group (A1) is a resin comprising a structural unit represented by formula (a3A) or a structural unit represented by formula (a3B): wherein, in formula (a3A), Ra1, Ra2 and Ra3 each independently represent an alkyl group having 1 to 8 carbon atoms or an alicyclic hydrocarbon group having 3 to 20 carbon atoms, or Ra1 and Ra2 are bonded to each other to form a ring having 3 to 20 carbon atoms together with carbon atoms to which Ra1 and Ra2 are bonded, and Ra3 represents an alkyl group having 1 to 8 carbon atoms or an alicyclic hydrocarbon group having 3 to 20 carbon atoms, Rab represents a hydroxy group, an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, and p represents 0, 1, 2 or 3, and when p is 2 or 3, Rab may be the same or different: wherein, in formula (a3B), Ra1′ and Ra2′ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, Ra3′ represents a hydrocarbon group having 1 to 20 carbon atoms, or Ra1′ represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and Ra2′ and Ra3′ are bonded to each other to form an heterocyclic ring having 3 to 20 carbon atoms together with carbon atoms and oxygen atoms to which Ra2′ and Ra3′ are bonded, a methylene group included in the hydrocarbon group having 1 to 20 carbon atoms and the heterocyclic ring having 3 to 20 carbon atoms may be replaced by an oxygen atom or a sulfur atom, Rab represents a hydroxy group, an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, and p represents 0, 1, 2 or 3, and when p is 2 or 3, Rab may be the same or different. ### Claim 7 (depends on 1) The resist composition according to claim 1, wherein the alkali-soluble resin (A2) is a resin which comprises a structural unit having a carboxy group or a hydroxy group and does not comprise a structural unit having an acid-labile group. ### Claim 8 (depends on 1) The resist composition according to claim 1, further comprising a quencher (C). ### Claim 9 (depends on 1) A method for producing a resist pattern, which comprises: (1) a step of applying the resist composition according to claim 1 on a metal surface of a substrate having the metal surface, (2) a step of drying the applied composition to form a composition layer, (3) a step of exposing the composition layer, and (4) a step of developing the exposed composition layer. ### Claim 10 (depends on 1) A method for producing a plated molded article, which comprises: (1) a step of applying the resist composition according to claim 1 on a metal surface of a substrate having the metal surface, (2) a step of drying the applied composition to form a composition layer, (3) a step of exposing the composition layer, (4) a step of developing the exposed composition layer, (5) a step of forming a plated molded article using the resist pattern thus obtained as a mold, and (6) a step of stripping the resist pattern.