# US 8,465,902 B2 · Underlayer coating composition and processes thereof > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,465,902 B2 - Document ID: US8465902B2 - Status: Granted - Kind: B2 - Application number: 13/023,291 - Filed: 2011-02-08 - Published: 2012-08-09 - Granted: 2013-06-18 - Earliest claimed: 2011-02-08 - Assignees: AZ Electronic Materials USA Corp. - Applicants: Huirong Yao; Zachary Bogusz; Guanyang Lin; Mark Neisser - Inventors: Huirong Yao; Zachary Bogusz; Guanyang Lin; Mark Neisser - Web page: https://patentgrep.com/patent/US8465902B2 ## CPC - G03F 7/091: {characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement} - C09D 161/24: with urea or thiourea - G03F 7/0046: {with perfluoro compounds, e.g. for dry lithography (G03F7/0048 takes precedence)} - G03F 7/11: having cover layers or intermediate layers, e.g. subbing layers {(G03F7/091 - G03F7/093, B41N3/03 take precedence)} - 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) - 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 invention relates to an underlayer coating composition comprising a polymer, where the polymer comprises at least one hydroxyaromatic unit in the backbone of the polymer phenol which has a pendant group comprising a fluoro or iodo moiety, and at least one unit comprising an aminoplast. The invention further relates to a process for forming an image using the composition, especially for EUV. ## Claims ### Claim 1 An underlayer coating composition comprising a polymer, where the polymer comprises at least one hydroxyaromatic unit in the backbone of the polymer comprising a fluoro or iodo moiety, and at least one unit comprising an aminoplast, further where the hydroxyaromatic unit with the fluoro moiety has structure (1), where, R1 is fluoro moiety, R2 is fluoro moiety and R3 is selected from a group consisting of an iodo moiety, a fluoro moiety, hydrogen, hydroxyl, (C1-C4)alkyl, hydroxy(C1-C4)alkyl, OC1-C4alkyl, (C═O)(C1-C4)alkyl, C1-C4alkylO(C1-C4)alkyl, C1-C4alkyl(C═O)(C1-C4)alkyl and C(O)O(C1-C4)alkyl. ### Claim 2 (depends on 1) The composition of claim 1, where the fluoro moiety is selected from F, C1-C4fluoroalkyl, C1-C4 hydroxyfluoroalkyl, OC1-C4fluoroalkyl C(O)(C1-C4)fluoroalkyl, and C(O)O(C1-C4)fluoroalkyl. ### Claim 3 (depends on 1) The composition of claim 1, where the unit comprising an aminoplast is derived from a glycoluril monomer. ### Claim 4 (depends on 1) The composition of claim 1, where the unit comprising an aminoplast is derived from a urea/formaldehyde oligomer. ### Claim 5 (depends on 1) The composition of claim 1, where the polymer further comprises a phenolic unit free of a fluoro or iodo moiety. ### Claim 6 (depends on 1) The composition of claim 1, where the composition further comprises a thermal acid generator. ### Claim 7 (depends on 1) The composition of claim 1, where the composition further comprises a polyester polymer. ### Claim 8 (depends on 1) The composition of claim 1, where the composition further comprises a glycoluril polymer different from the polymer of claim 1. ### Claim 9 (depends on 1) The composition of claim 1, wherein the hydroxyaromatic unit is naphthol. ### Claim 10 (depends on 1) The composition of claim 1 further comprising a solvent. ### Claim 11 (depends on 1) The composition of claim 1 further comprising a secondary polymer. ### Claim 12 (depends on 1) The composition or polymer of claim 1 having a fluoro or iodo content in the range of 1% to 30% by weight. ### Claim 13 (depends on 1) The composition of claim 1, where the hydroxyaromatic unit is derived from ### Claim 14 (depends on 1) The composition of claim 1, where the composition is free of an external crosslinker. ### Claim 15 (depends on 1) A process for manufacturing a microelectronic device, comprising; a) providing a substrate with a layer of an underlayer coating composition from claim 1; b) coating a photoresist layer above the underlayer coating ; c) imagewise exposing the photoresist layer; d) developing the photoresist layer with an aqueous alkaline developing solution. ### Claim 16 (depends on 15) The process of claim 15, where the underlayer coating layer has k value in the range of about 0.05 to about 1.0. ### Claim 17 (depends on 15) The process of claim 15, where the underlayer coating layer has k value in the range of about 0.05 to about 0.5. ### Claim 18 (depends on 15) The process of claim 15, where the photoresist is imageable with radiation from about 260 nm to about 12 nm. ### Claim 19 (depends on 15) The process according to claim 15, where the developing solution is an aqueous solution comprising a hydroxide base. ### Claim 20 (depends on 1) The composition of claim 1, where the hydroxyaromatic unit with the iodo moiety has structure (1), where, R1 is selected from an iodo moiety, R2 and R3 are independently selected from an iodo moiety, a fluoro moiety, hydrogen, hydroxyl, (C1-C4)alkyl, hydroxy(C1-C4)alkyl, OC1-C4alkyl, (C═O)(C1-C4)alkyl, C1-C4alkylO(C1-C4)alkyl, C1-C4alkyl(C═O)(C1-C4)alkyl, C(O)O(C1-C4)alkyl and R2 and R3 are connected to form hydroxyaromatic ring fused to the phenol.