# US 11,441,053 B2 · Composition for forming adhesive film for imprinting, adhesive film, laminate, method for producing cured product pattern, and method for manufacturing circuit substrate > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,441,053 B2 - Document ID: US11441053B2 - Status: Granted - Kind: B2 - Application number: 16/546,996 - Filed: 2019-08-21 - Published: 2019-12-19 - Granted: 2022-09-13 - Earliest claimed: 2017-02-28 - Assignees: FUJIFILM Corporation - Applicants: FUJIFILM Corporation - Inventors: Naoya Shimoju; Akinori Shibuya; Yuichiro Goto - Web page: https://patentgrep.com/patent/US11441053B2 ## CPC - C09J 7/30: characterised by the adhesive composition - B32B 3/263: {characterised by a layer having non-uniform thickness} - B32B 7/12: using interposed adhesives or interposed materials with bonding properties - B32B 9/005: {comprising one layer of ceramic material, e.g. porcelain, ceramic tile (layered products with at least two ceramic layers composed mainly of ceramic B32B18/00)} - B32B 9/045: {of synthetic resin} - B32B 27/308: {comprising acrylic (co)polymers} - B32B 37/12: characterised by using adhesives - B32B 37/1207: {Heat-activated adhesive (B32B37/04 takes precedence)} - B32B 37/15: with at least one layer being manufactured and immediately laminated before reaching its stable state, e.g. in which a layer is extruded and laminated while in semi-molten state - B32B 38/0008: {Electrical discharge treatment, e.g. corona, plasma treatment; wave energy or particle radiation (heat treatment B32B38/0036)} - B32B 38/06: Embossing - C08F 2/48: by ultraviolet or visible light - C08L 33/04: Homopolymers or copolymers of esters {(C08L43/04 takes precedence)} - C08L 33/14: of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen - C09J 5/00: Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers - C09J 133/04: Homopolymers or copolymers of esters {(C09J143/04 takes precedence)} - C09J 133/14: of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen - H10P 76/20: of masks comprising organic materials - B29C 59/02: by mechanical means, e.g. pressing {(B29C59/007 takes precedence; embossing expanded porous articles B29C44/5627)} - B29K 2105/0097: {Glues or adhesives, e.g. hot melts or thermofusible adhesives} - B32B 2038/0076: {Curing, vulcanising, cross-linking} - B32B 2250/02: 2 layers - B32B 2255/26: Polymeric coating - B32B 2305/72: Cured, e.g. vulcanised, cross-linked - B32B 2310/0806: using electromagnetic radiation - B32B 2315/02: Ceramics - B32B 2333/08: Polymers of acrylic acid esters, e.g. PMA, i.e. polymethylacrylate - B32B 2457/08: PCBs, i.e. printed circuit boards - C08K 5/06: Ethers; Acetals; Ketals; Ortho-esters - C09J 2203/318: for the production of liquid crystal displays - C09J 2203/326: for bonding electronic components such as wafers, chips or semiconductors - C09J 2301/204: the adhesive coating being discontinuous - C09J 2301/408: additives as essential feature of the adhesive layer - C09J 2301/416: use of irradiation - C09J 2301/502: process for debonding adherents - C09J 2433/00: Presence of (meth)acrylic polymer - G03F 7/0002: {Lithographic processes using patterning methods other than those involving the exposure to radiation, e.g. by stamping} - C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H) - B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - H10P: GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10 - B29C: SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING (making preforms B29B11/00; making laminated products by combining previously unconnected layers which become one product whose layers will remain together B32B37/00 - B32B41/00) - B29K: INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR {MOULDS, } REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) - 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 There are provided a composition for forming an adhesive film for imprinting having excellent adhesiveness and wettability, an adhesive film, a laminate, a method for producing a cured product pattern, and a method for manufacturing a circuit substrate. A composition for forming an adhesive film for imprinting contains a resin having a polymerizable group; and a solvent, in which the resin has at least one kind of a repeating unit derived from a polymerizable compound having a C log P value less than or equal to 0, and solubility of the resin in water at 25° C. is greater than or equal to 1 mass %, provided that the C log P value is a coefficient showing affinity of an organic compound with respect to water and 1-octanol. ## Claims ### Claim 1 A composition for forming an adhesive film for imprinting, the composition comprising: a resin (A) having a polymerizable group, said resin (A) having at least one kind of a repeating unit derived from a polymerizable compound having a ClogP value less than or equal to 0; at least one of a resin (B) which has a polymerizable group and does not have a repeating unit derived from a polymerizable compound having a ClogP value less than or equal to 0, and a resin (C) which does not have a polymerizable group and has a repeating unit derived from a polymerizable compound having a ClogP value less than or equal to 0; and a solvent, wherein solubility of the resin (A) in water at 25° C. is greater than or equal to 1 mass %, provided that the ClogP value is a coefficient showing affinity of an organic compound with respect to water and 1-octanol, the polymerizable compound has an -alkylene group-oxygen atom-structure, in which the alkylene group has 1 to 6 carbon atoms, and the number of repeating units of the -alkylene group-oxygen atom-structure is 2 to 90. ### Claim 2 (depends on 1) The composition for forming an adhesive film for imprinting according to claim 1, wherein the solvent is contained in the composition for forming an adhesive film for imprinting in a proportion of 85.0 to 99.9 mass %. ### Claim 3 (depends on 1) The composition for forming an adhesive film for imprinting according to claim 1, wherein the polymerizable group is a (meth)acrylic group. ### Claim 4 (depends on 1) The composition for forming an adhesive film for imprinting according to claim 1, further comprising: a non-polymerizable alkylene glycol compound. ### Claim 5 (depends on 1) The composition for forming an adhesive film for imprinting according to claim 1, wherein the solvent contains water. ### Claim 6 (depends on 1) The composition for forming an adhesive film for imprinting according to claim 1, wherein the solvent contains an organic solvent. ### Claim 7 (depends on 1) The composition for forming an adhesive film for imprinting according to claim 1, wherein the resin (A) is a (meth)acrylic resin. ### Claim 8 (depends on 1) The composition for forming an adhesive film for imprinting according to claim 1, wherein the alkylene group of the -alkylene group-oxygen atom-structure is an ethylene group. ### Claim 9 (depends on 1) The composition for forming an adhesive film for imprinting according to claim 1, wherein the number of repeating units of the -alkylene group-oxygen atom-structure is 4.5 to 90. ### Claim 10 (depends on 1) The composition for forming an adhesive film for imprinting according to claim 1, wherein the repeating unit derived from the polymerizable compound having a ClogP value less than or equal to 0 is represented by Formula (II) or Formula (III): wherein in Formulae (II) to (III), each R independently represents a hydrogen atom, a methyl group, or a hydroxymethyl group, each T independently represents a single bond, *—C(═O)O—, or *—C(═O)NH—, bonding to a main chain is carried out on a * side, each L independently represents a single bond or a divalent linking group, P represents a polymerizable group, and Q is a divalent linking group or a monovalent linking group, both containing the -alkylene group-oxygen atom-structure. ### Claim 11 (depends on 1) The composition for forming an adhesive film for imprinting according to claim 1, wherein the repeating unit derived from the polymerizable compound having a ClogP value less than or equal to 0 is any of the following: wherein in the first repeating unit above n represents 4.5, in the second repeating unit above n represents 90, in the third repeating unit above n represents 13.2, in the fourth and fifth repeating units above n represents 10, and in the sixth repeating unit above n represents 8. ### Claim 12 (depends on 1) An adhesive film formed from the composition for forming an adhesive film for imprinting according to claim 1. ### Claim 13 (depends on 12) The adhesive film according to claim 12, wherein a critical surface tension of the adhesive film is greater than or equal to 45 mN/m. ### Claim 14 (depends on 12) A laminate comprising: a substrate; and an adhesive film positioned on a surface of the substrate, wherein the adhesive film is the adhesive film according to claim 12. ### Claim 15 (depends on 14) The laminate according to claim 14, wherein the adhesive film interacts with the substrate by at least one selected from the group consisting of a covalent bond, an ionic bond, and a hydrogen bond. ### Claim 16 (depends on 14) The laminate according to claim 14, further comprising: a layer formed from a curable composition for imprinting on a surface of the adhesive film in order of the substrate, the adhesive film, and the layer formed from the curable composition for imprinting. ### Claim 17 (depends on 14) The laminate according to claim 14, further comprising: a cured product pattern formed from a curable composition for imprinting on a surface of the adhesive film in order of the substrate, the adhesive film, and the cured product pattern. ### Claim 18 (depends on 1) A method for producing a cured product pattern, the method comprising: an adhesive film formation step of forming an adhesive film by applying the composition for forming an adhesive film for imprinting according to claim 1 onto a substrate; an application step of applying a curable composition for imprinting onto a surface of the adhesive film; a mold contact step of bringing the curable composition for imprinting into contact with a mold having a pattern for transferring a pattern shape; a light irradiation step of irradiating the curable composition for imprinting with light to obtain a cured product; and a release step of separating the cured product from the mold. ### Claim 19 (depends on 18) A method for manufacturing a circuit substrate, the method comprising: a step of obtaining a cured product pattern through the production method according to claim 18.