# US 10,504,739 B2 · Curable composition for optical imprinting and pattern forming method > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,504,739 B2 - Document ID: US10504739B2 - Status: Granted - Kind: B2 - Application number: 15/083,352 - Filed: 2016-03-29 - Published: 2016-07-21 - Granted: 2019-12-10 - Earliest claimed: 2013-09-30 - Assignees: FUJIFILM Corporation - Applicants: FUJIFILM Corporation - Inventors: Hirotaka Kitagawa; Yuichiro Goto - Web page: https://patentgrep.com/patent/US10504739B2 ## CPC - H10P 50/692: {characterised by their composition, e.g. multilayer masks or materials} - C09D 4/06: {Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond} in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00 - C09D 11/101: Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing - C09D 11/30: Inkjet printing inks - G03F 7/0002: {Lithographic processes using patterning methods other than those involving the exposure to radiation, e.g. by stamping} - G03F 7/027: Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds (G03F7/075 takes precedence) - 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 7/0388: {with ethylenic or acetylenic bands in the side chains of the photopolymer} - H10P 14/6346: {using printing, e.g. ink-jet printing} - H10P 14/6536: {by exposure to radiation, e.g. visible light} - H10P 14/683: {carbon-based polymeric organic materials, e.g. polyimides, poly cyclobutene or PVC} - H10P 50/695: {characterised by the process involved to create the mask, e.g. lift-off masks or sidewalls or to modify the mask} - Y10T 428/24802: Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.] - H10P: GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10 - 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) - 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) - Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION ## Abstract A curable composition for optical imprinting which is excellent in ink jet adequacy and releasability, a pattern forming method, a fine pattern, and a method for manufacturing a semiconductor device are provided. The curable composition for optical imprinting contains a polymerizable compound (A), a photopolymerization initiator (B), and a compound (C) expressed by General Formula (I); in General Formula (I), A represents a dihydric to hexahydric polyhydric alcohol residue. p represents 0 to 2, l q represents 1 to 6, p+q represents an integer of 2 to 6, each of m and n independently represents 0 to 20. r expressed by Formula (1) is 6 to 20. Each R independently represents an alkyl group having 1 to 10 carbon atoms, an aryl group, or an acyl group. ## Claims ### Claim 1 A curable composition for optical imprinting, comprising: a polymerizable compound (A); a photopolymerization initiator (B); and a compound (C) expressed by General Formula (I), wherein, in General Formula (I), A represents a trihydric to hexahydric polyhydric alcohol residue, p represents 0 to 2, q represents 1 to 6, p+q represents an integer of 2 to 6, m represents an average number of addition of ethyleneoxide, n represents an average number of addition of propyleneoxide, each of m and n independently represents 0 to 20, r expressed by Formula (1) is 6 to 20; r=(sum of m)+(sum of n) (1) and each R independently represents an alkyl group having 1 to 10 carbon atoms, an aryl group, an acetyl group, a propionyl group or a benzoyl group, wherein, when each of m and n are 2 or greater, the distribution thereof is random or blocked. ### Claim 2 (depends on 1) The curable composition for optical imprinting according to claim 1, wherein the content of the compound (C) expressed by General Formula (I) is 3 mass % to 15 mass % with respect to the total mass of the composition except for solvent. ### Claim 3 (depends on 1) The curable composition for optical imprinting according to claim 1, wherein the viscosity of the curable composition for optical imprinting at 23° C. is 15 mPa·s or less, and the surface tension thereof is 25 mN/m to 35 mN/m. ### Claim 4 (depends on 1) The curable composition for optical imprinting according to claim 1, wherein, in General Formula (I), R is an alkyl group having 1 to 4 carbon atoms. ### Claim 5 (depends on 1) The curable composition for optical imprinting according to claim 1, wherein, in General Formula (I), p is 0. ### Claim 6 (depends on 1) The curable composition for optical imprinting according to claim 1, wherein, in General Formula (I), m is 0. ### Claim 7 (depends on 1) The curable composition for optical imprinting according to claim 1, wherein the polyhydric alcohol residue has 2 to 10 carbon atoms. ### Claim 8 (depends on 1) The curable composition for optical imprinting according to claim 1, wherein, in General Formula (I), n is 0. ### Claim 9 (depends on 1) The curable composition for optical imprinting according to claim 1, wherein the polymerizable compound (A) is a (meth)acrylate compound. ### Claim 10 (depends on 1) The curable composition for optical imprinting according to claim 1, wherein the polymerizable compound (A) is a compound having an aromatic group. ### Claim 11 (depends on 1) The curable composition for optical imprinting according to claim 1, wherein the content of a solvent is 5 mass % or less with respect to the total composition. ### Claim 12 (depends on 1) The curable composition for optical imprinting according to claim 1, wherein, in General Formula (I), p is 0, and the content of a solvent is 5 mass % or less with respect to the total composition. ### Claim 13 (depends on 1) The curable composition for optical imprinting according to claim 1, in General Formula (I), m is 0, and the content of a solvent is 5 mass % or less with respect to the total composition. ### Claim 14 (depends on 1) A pattern forming method, comprising: applying the curable composition for optical imprinting according to claim 1 on a base material or a mold having a fine pattern; and performing photoirradiation in a state in which the curable composition for optical imprinting is interposed between the mold and the base material. ### Claim 15 (depends on 14) The pattern forming method according to claim 14, wherein the method of applying the curable composition for optical imprinting on the base material or the mold having the fine pattern is an ink jet method. ### Claim 16 (depends on 14) A fine pattern obtained by the pattern forming method according to claim 14. ### Claim 17 (depends on 16) A method for manufacturing a semiconductor device using the pattern according to claim 16 as an etching mask.