# US 7,611,819 B2 · Resist composition, method for forming resist pattern, and semiconductor device and method for manufacturing the same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 7,611,819 B2 - Document ID: US7611819B2 - Status: Granted - Kind: B2 - Application number: 11/476,172 - Filed: 2006-06-28 - Published: 2007-09-27 - Granted: 2009-11-03 - Earliest claimed: 2006-03-24 - Assignees: Fujitsu Limited - Inventors: Koji Nozaki; Miwa Kozawa - Web page: https://patentgrep.com/patent/US7611819B2 ## CPC - H10P 76/204: {of organic photoresist masks} - G03F 7/40: Treatment after imagewise removal, e.g. baking - H10P 50/71: {using masks for conductive or resistive materials} - H10P 50/73: {using masks for insulating materials} - H10P 76/4088: {Processes for improving the resolution of the masks} - Y10S 430/106: Binder containing - Y10S 430/114: Initiator containing - H10P: GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10 - 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) - Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS ## Abstract The present invention provides a resist composition which enables uniformly thickening a resist pattern with a resist pattern thickening material, regardless of the direction, spacing variations of the resist pattern, and the components of the resist pattern thickening material and enables forming a fine space pattern of resist, exceeding exposure limits of light sources of exposure devices at low cost, easily, and efficiently. The resist composition contains an alicyclic compound (melting point: 90° C. to 150° C.), and a resin. The method for manufacturing a semiconductor device includes forming a resist pattern on a surface of a workpiece to be processed by using a resist composition and applying a resist pattern thickening material on the surface of the workpiece so as to cover the surface of the resist pattern to thicken the resist pattern; and patterning the surface of the workpiece by etching thereof using the thickened resist pattern as a mask. ## Claims ### Claim 1 A resist composition comprising: an alicyclic compound; and a resin wherein the alicyclic compound is at least any one of adamantane compounds and norbornane compounds, wherein the adamantane compounds are represented by the following Structural Formulae (1) to (5), and the norbornane compounds are represented by the following Structural Formulae (6) to (8), and wherein the resist composition does not comprise water ### Claim 2 (depends on 1) The resist composition according to claim 1, wherein the resin is at least one selected from acrylic resists, cycloolefin-maleic acid anhydride resists and cycloolefin resists. ### Claim 3 (depends on 1) The resist composition according to claim 1, wherein the content of the alicyclic compound is 0.01% by mass to 5% by mass relative to the mass of the resin. ### Claim 4 (depends on 1) The resist composition according to claim 1, wherein the resist composition is exposed with at least one selected from the group consisting of g-rays, i-rays, KrF excimer laser light, ArF excimer laser light, F2 excimer laser light, EUV light, electron beams, and x-rays. ### Claim 5 A method for forming a resist pattern comprising: forming a resist pattern on a surface of a workpiece to be processed by using a resist composition; and applying a resist pattern thickening material on the surface of the workpiece so as to cover the surface of the resist pattern, wherein the resist composition comprises at least an alicyclic compound and a resin, wherein the alicyclic compound is at least any one of adamantane compounds and norbornane compounds, wherein the adamantane compounds are represented by the following Structural Formulae (1) to (5), and the norbornane compounds are represented by the following Structural Formulae (6) to (8), and wherein the resist composition does not comprise water ### Claim 6 (depends on 5) The method for forming a resist pattern according to claim 5, wherein the resist pattern thickening material is water-soluble or alkali-soluble. ### Claim 7 (depends on 6) The method for forming a resist pattern according to claim 6, wherein the resist pattern thickening material comprises any one of a water-soluble resin and an alkali-soluble resin, and the resin is at least one selected from the group consisting of polyvinyl alcohols, polyvinyl acetals, polyvinyl acetates, and tannins. ### Claim 8 (depends on 5) The method for forming a resist pattern according to claim 5, wherein the resist pattern thickening material comprises a crosslinker, and the crosslinker is at least one selected from the group consisting of melamine derivatives, urea derivatives, and uril derivatives. ### Claim 9 (depends on 5) The method for forming a resist pattern according to claim 5, wherein the resist pattern thickening material comprises a compound represented by the following General Formula (1): where X represents a functional group represented by the following General Formula (2); Y represents at least one selected from the group consisting of hydroxyl groups, amino groups, amino groups substituted with alkyl groups, alkoxy groups, alkoxy-carbonyl groups, and alkyl groups; the number of substitutions is an integer of 0 to 3; “m” is an integer of 1 or more, and “n” is an integer of 0 or more where R1 and R2 may be the same to each other or different from each other, and respectively represent hydrogen or a substituent group; Z represents at least one selected from the group consisting of hydroxyl groups, amino groups, amino groups substituted with alkyl groups, and alkoxy groups; and the number of substitutions is an integer of 0 to 3. ### Claim 10 (depends on 9) The method for forming a resist pattern according to claim 9, wherein in the General Formula (1), “m” is an integer of 1. ### Claim 11 (depends on 5) The method for forming a resist pattern according to claim 5, wherein the resist pattern thickening material comprises a surfactant, and the surfactant is at least one selected from the group consisting of polyoxyethylene-polyoxypropylene condensation compounds, polyoxy alkylene alkyl ether compounds, polyoxyethylene alkyl ether compounds, polyoxyethylene derivative compounds, sorbitan fatty acid ester compounds, glycerine fatty acid ester compounds, primary alcohol ethoxylate compounds, phenol ethoxylate compounds, nonyl phenol ethoxylate compounds, octyl phenol ethoxylate compounds, lauryl alcohol ethoxylate compounds, oleyl alcohol ethoxylate compounds, fatty acid ester compounds, amide compounds, natural alcohol compounds, ethylenediamine compounds, secondary alcohol ethoxylate compounds, alkyl cationic compounds, amide quaternary cationic compounds, ester quaternary cationic compounds, amine oxide compounds, and betaine compounds. ### Claim 12 (depends on 5) The method for forming a resist pattern according to claim 5, further comprising heating the surface of the resist pattern with the resist pattern thickening material applied thereon. ### Claim 13 (depends on 12) The method for forming a resist pattern according to claim 12, wherein the resist pattern is heated at a temperature near the melting point of the alicyclic compound in the resist composition. ### Claim 14 (depends on 13) The method for forming a resist pattern according to claim 13, wherein the heating temperature is the melting temperature of the alicyclic compound or more. ### Claim 15 (depends on 5) The method for forming a resist pattern according to claim 5, further comprising subjecting the surface of the resist pattern with the resist pattern thickening material applied thereon to a developing treatment. ### Claim 16 (depends on 15) The method for forming a resist pattern according to claim 15, wherein the developing treatment is performed using at least water. ### Claim 17 A method for manufacturing a semiconductor device comprising: forming a resist pattern on a surface of a workpiece to be processed by using a resist composition, and by applying a resist pattern thickening material over the surface of the workpiece so as to cover the surface of the resist pattern to thereby thicken the resist pattern; and patterning the surface of the workpiece by etching the surface of the workpiece using the thickened resist pattern as a mask, wherein the resist composition comprises an alicyclic compound and a resin, wherein the alicyclic compound is at least any one of adamantane compounds and norbornane compounds, wherein the adamantane compounds are represented by the following Structural Formulae (1) to (5), and the norbornane compounds are represented by the following Structural Formulae (6) to (8),and wherein the resist composition does not comprise water ### Claim 18 (depends on 17) The method for manufacturing a semiconductor device according to claim 17, further comprising applying a nonionic surfactant over a surface of the resist pattern before forming the thickened resist pattern, wherein the nonionic surfactant is at least one selected from the group consisting of polyoxyethylene-polyoxypropylene condensation compounds, polyoxy alkylene alkyl ether compounds, polyoxyethylene alkyl ether compounds, polyoxyethylene derivative compounds, sorbitan fatty acid ester compounds, glycerine fatty acid ester compounds, primary alcohol ethoxylate compounds, and phenol ethoxylate compounds.