# US 10,865,304 B2 · Heat-curable resin composition, heat-curable resin film and semiconductor device > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,865,304 B2 - Document ID: US10865304B2 - Status: Granted - Kind: B2 - Application number: 16/557,467 - Filed: 2019-08-30 - Published: 2020-03-12 - Granted: 2020-12-15 - Earliest claimed: 2018-09-12 - Assignees: Shin-Etsu Chemical Co., Ltd. - Applicants: Shin-Etsu Chemical Co., Ltd. - Inventors: Naoyuki Kushihara; Yuki Kudo; Kazuaki Sumita; Yoshihiro Tsutsumi; Yoshihira Hamamoto - Web page: https://patentgrep.com/patent/US10865304B2 ## CPC - C08L 63/00: Compositions of epoxy resins; Compositions of derivatives of epoxy resins - B01J 31/0247: {Imides, amides or imidates (R-C=NR(OR))} - C08G 59/14: Polycondensates modified by chemical after-treatment - C08G 59/68: characterised by the catalysts used - C08G 59/686: {containing nitrogen} - C08J 5/18: Manufacture of films or sheets - C08K 5/14: Peroxides - C08K 5/3445: Five-membered rings - C08L 79/085: {Unsaturated polyimide precursors} - C09D 183/06: containing silicon bound to oxygen-containing groups (C09D183/12 takes precedence) - C08J 2363/04: Epoxynovolacs - C08J 2383/10: Block- or graft-copolymers containing polysiloxane sequences - C08J 2463/00: Characterised by the use of epoxy resins; Derivatives of epoxy resins - C08K 5/3415: Five-membered rings - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29) - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) - 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 Provided is a heat-curable resin composition exhibiting a superior handling property and workability in the form of a film, having a high adhesion to a base material, and capable of yielding a cured product with a low elasticity. The heat-curable resin composition contains: (A) 90 to 10 parts by mass of a silicone-modified epoxy resin; (B) 10 to 90 parts by mass of a maleimide compound having a weight-average molecular weight (Mw) of 2,500 to 50,000; and (C) a curing catalyst, provided that a total of the components (A) and (B) is 100 parts by mass. ## Claims ### Claim 1 A heat-curable resin composition comprising: (A) 90 to 10 parts by mass of a silicone-modified epoxy resin; (B) 10 to 90 parts by mass of a maleimide compound having a weight-average molecular weight (Mw) of 2,500 to 50,000; and (C) a curing catalyst, provided that a total of the components (A) and (B) is 100 parts by mass. ### Claim 2 (depends on 1) The heat-curable resin composition according to claim 1, further comprising: (A′) an epoxy resin other than the silicone-modified epoxy resin (A). ### Claim 3 (depends on 1) The heat-curable resin composition according to claim 1, wherein the silicone-modified epoxy resin (A) is at least one of silicone-modified epoxy resins represented by the following formulae (8) and (9): wherein each X independently represents a hydrogen atom, a substituted or unsubstituted monovalent hydrocarbon group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted alkoxyalkyl group; R3 represents a substituted or unsubstituted monovalent hydrocarbon group having no aliphatic unsaturated groups; R4 represents a glycidyl group; R5 represents a substituted or unsubstituted divalent hydrocarbon group that may have an oxygen atom(s); each R6 independently represents a hydrogen atom, a methyl group or a trifluoromethyl group; k represents an integer of not smaller than 8; p represents an integer of not smaller than 0. ### Claim 4 (depends on 1) The heat-curable resin composition according to claim 1, wherein the maleimide compound (B) is a bismaleimide compound represented by the following formula (1): wherein n represents an integer of 1 to 50, R1 independently represents one or more divalent groups selected from: a linear or branched alkylene group having 1 to 40 carbon atoms; a divalent cyclic hydrocarbon group that has 3 to 20 carbon atoms and may have a hetero atom(s); —O—; —NH—; —S—; and —SO2—. ### Claim 5 (depends on 1) The heat-curable resin composition according to claim 1, wherein the maleimide compound (B) is represented by the following general formula (2): wherein each A independently represents a tetravalent organic group having an aromatic or aliphatic ring; B represents an alkylene chain having 6 to 18 carbon atoms and a divalent aliphatic ring that may contain a hetero atom; each Q independently represents a linear alkylene group having not less than 6 carbon atoms; each R independently represents a linear or branched alkyl group having not less than 6 carbon atoms; n′ represents an integer of 1 to 10; m represents an integer of 0 to 10. ### Claim 6 (depends on 5) The heat-curable resin composition according to claim 5, wherein A in the general formula (2) has any one of the following structures: wherein bonds in the above structural formulae that are yet unbonded to substituent groups are to be bonded to carbonyl carbons forming cyclic imide structures in the general formula (2). ### Claim 7 (depends on 1) The heat-curable resin composition according to claim 1, wherein the curing catalyst (C) is at least one selected from (C1) a curing agent for epoxy resin, (C2) a curing accelerator and (C3) a polymerization initiator. ### Claim 8 (depends on 1) The heat-curable resin composition according to claim 1, wherein the curing catalyst (C) is an imidazole compound. ### Claim 9 (depends on 1) A heat-curable resin film containing the heat-curable resin composition according to claim 1. ### Claim 10 (depends on 9) A semiconductor device encapsulated by the heat-curable resin film according to claim 9.