# US 8,771,917 B2 · Monomers, polymers, photoresist compositions and methods of forming photolithographic patterns > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,771,917 B2 - Document ID: US8771917B2 - Status: Granted - Kind: B2 - Application number: 13/341,931 - Filed: 2011-12-31 - Published: 2013-01-10 - Granted: 2014-07-08 - Earliest claimed: 2010-12-31 - Assignees: Rohm and Haas Electronics Materials LLC; Dow Global Technologies LLC - Applicants: Matthias S. Ober; Young Cheol Bae; Yi Liu; Seung-Hyun Lee; Jong Keun Park - Inventors: Matthias S. Ober; Young Cheol Bae; Yi Liu; Seung-Hyun Lee; Jong Keun Park - Web page: https://patentgrep.com/patent/US8771917B2 ## CPC - C08F 220/20: of polyhydric alcohols or phenols {, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate} - C07D 307/93: condensed with a ring other than six-membered - C07D 317/24: esterified - C08F 24/00: Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a heterocyclic ring containing oxygen (cyclic esters of polyfunctional acids C08F18/00; cyclic anhydrides of unsaturated acids C08F20/00, C08F22/00) - G03F 7/0382: {the macromolecular compound being present in a chemically amplified negative photoresist composition} - G03F 7/0397: {the macromolecular compound having an alicyclic moiety in a side chain} - G06F 7/38: Methods or arrangements for performing computations using exclusively denominational number representation, e.g. using binary, ternary, decimal representation - Y10S 430/111: Polymer of unsaturated acid or ester - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - 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) - G06F: ELECTRIC DIGITAL DATA PROCESSING (computer systems based on specific computational models G06N) - Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS ## Abstract Provided are (meth)acrylate monomers containing acetal moieties, polymers containing a unit formed from such a monomer and photoresist compositions containing such a polymer. The monomers, polymers and photoresist compositions are useful in forming photolithographic patterns. Also provided are substrates coated with the photoresist compositions, methods of forming photolithographic patterns and electronic devices. The compositions, methods and coated substrates find particular applicability in the manufacture of semiconductor devices. ## Claims ### Claim 1 A polymer, comprising: a first unit formed from a monomer of the following general formula (I): wherein: L represents a single bond or a C1 to C10 organic group; R1 represents hydrogen or a C1 to C3 alkyl group; R2 each independently represents a hydrogen atom or a C1 to C10 organic group; R3 each independently represents a hydrogen atom or a C1 to C10 organic group, those bonded to a common carbon atom together optionally forming a ring; and R4 each independently represents a C1 to Cto organic group, those bonded to a common carbon atom together optionally forming a ring; and a second unit comprising a lactone moiety. ### Claim 2 A photoresist composition, comprising: a polymer, comprising: a unit formed from a monomer of the following general formula (I): wherein: L represents a single bond or a C1 to C10 organic group; R1 represents hydrogen or a C1 to C3 alkyl group; R2 each independently represents a hydrogen atom or a C1 to C10 organic group; R3 each independently represents a hydrogen atom or a C1 to C10 organic group, those bonded to a common carbon atom together optionally forming a ring; and R4 each independently represents a C1 to C10 organic group, those bonded to a common carbon atom together optionally forming a ring; and a photoacid generator. ### Claim 3 (depends on 2) The photoresist composition of claim 2, wherein the polymer further comprises a second unit comprising a lactone moiety. ### Claim 4 (depends on 3) The photoresist composition of claim 3, wherein the polymer further comprises a third unit comprising an ether, an ester, a polar group or an acid labile moiety, wherein the third unit is different from the first unit and the second unit. ### Claim 5 (depends on 2) The photoresist composition of claim 2, wherein the polymer further comprises a second unit formed from a monomer which is an acid-labile alkyl or alkyloxy (meth)acrylate. ### Claim 6 A coated substrate, comprising a substrate and a layer of a photoresist composition over a surface of the substrate; wherein the photoresist composition comprises: a polymer, comprising: a unit formed from a monomer of the following general formula (I): wherein: L represents a single bond or a C1 to C10 organic group; R1 represents hydrogen or a C1 to C3 alkyl group; R2 each independently represents a hydrogen atom or a C1 to C10 organic group; R3 each independently represents a hydrogen atom or a C1 to C10 organic group, those bonded to a common carbon atom together optionally forming a ring; and R4 each independently represents a C1 to C10 organic group, those bonded to a common carbon atom together optionally forming a ring; and a photoacid generator. ### Claim 7 A method of forming a photolithographic pattern, comprising: (a) providing a substrate comprising one or more layer to be patterned over a surface of the substrate; (b) applying a layer of a photoresist composition of over the one or more layer to be patterned; (c) patternwise exposing the photoresist composition layer to actinic radiation; (d) heating the exposed photoresist composition layer in a post-exposure bake process; and (e) applying a developer to the photoresist composition layer to remove a portion of the photoresist layer, thereby forming a photoresist pattern; wherein the photoresist composition comprises: a polymer, comprising: a unit formed from a monomer of the following general formula (I): wherein: L represents a single bond or a C1 to C10 organic group; R1 represents hydrogen or a C1 to C3 alkyl group; R2 each independently represents a hydrogen atom or a C1 to C10 organic group; R3 each independently represents a hydrogen atom or a C1 to C10 organic group, those bonded to a common carbon atom together optionally forming a ring; and R4 each independently represents a C1 to C10 organic group, those bonded to a common carbon atom together optionally forming a ring; and a photoacid generator. ### Claim 8 (depends on 7) The method of claim 7, wherein unexposed regions of the photoresist layer are removed by the developer to form the photoresist pattern. ### Claim 9 (depends on 8) The method of claim 8, wherein the developer is 2-heptanone. ### Claim 10 (depends on 8) The method of claim 8, wherein the polymer further comprises a second unit formed from a monomer which is an acid-labile alkyl or alkyloxy (meth)acrylate. ### Claim 11 (depends on 8) The method of claim 8, wherein the polymer further comprises a second unit comprising a lactone moiety. ### Claim 12 (depends on 11) The method of claim 11, wherein the polymer further comprises a third unit comprising an ether, wherein the third unit is different from the first unit and the second unit. ### Claim 13 (depends on 11) The method of claim 11, wherein the polymer further comprises a third unit comprising an ester, wherein the third unit is different from the first unit and the second unit. ### Claim 14 (depends on 11) The method of claim 11, wherein the polymer further comprises a third unit comprising a polar group, wherein the third unit is different from the first unit and the second unit. ### Claim 15 (depends on 11) The method of claim 11, wherein the polymer further comprises a third unit comprising an acid labile moiety, wherein the third unit is different from the first unit and the second unit. ### Claim 16 (depends on 4) The photoresist composition of claim 4, wherein the third unit comprises an ether, wherein the third unit is different from the first unit and the second unit. ### Claim 17 (depends on 4) The photoresist composition of claim 4, wherein the third unit comprises an ester, wherein the third unit is different from the first unit and the second unit. ### Claim 18 (depends on 4) The photoresist composition of claim 4, wherein the third unit comprises a polar group, wherein the third unit is different from the first unit and the second unit. ### Claim 19 (depends on 4) The photoresist composition of claim 4, wherein the third unit comprises an acid labile moiety, wherein the third unit is different from the first unit and the second unit. ### Claim 20 (depends on 6) The coated substrate of claim 6, wherein the polymer further comprises a second unit comprising a lactone moiety.