JPWO2018181989A1 - カルボニル構造を有するシリコン含有レジスト下層膜形成組成物 - Google Patents
カルボニル構造を有するシリコン含有レジスト下層膜形成組成物 Download PDFInfo
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- JPWO2018181989A1 JPWO2018181989A1 JP2019509407A JP2019509407A JPWO2018181989A1 JP WO2018181989 A1 JPWO2018181989 A1 JP WO2018181989A1 JP 2019509407 A JP2019509407 A JP 2019509407A JP 2019509407 A JP2019509407 A JP 2019509407A JP WO2018181989 A1 JPWO2018181989 A1 JP WO2018181989A1
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- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000001589 sorbitan tristearate Substances 0.000 description 1
- 235000011078 sorbitan tristearate Nutrition 0.000 description 1
- 229960004129 sorbitan tristearate Drugs 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- SFZCNBIFKDRMGX-UHFFFAOYSA-N sulfur hexafluoride Chemical compound FS(F)(F)(F)(F)F SFZCNBIFKDRMGX-UHFFFAOYSA-N 0.000 description 1
- 229960000909 sulfur hexafluoride Drugs 0.000 description 1
- 150000003866 tertiary ammonium salts Chemical class 0.000 description 1
- UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 0.000 description 1
- MCZDHTKJGDCTAE-UHFFFAOYSA-M tetrabutylazanium;acetate Chemical compound CC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MCZDHTKJGDCTAE-UHFFFAOYSA-M 0.000 description 1
- BRGJIIMZXMWMCC-UHFFFAOYSA-N tetradecan-2-ol Chemical compound CCCCCCCCCCCCC(C)O BRGJIIMZXMWMCC-UHFFFAOYSA-N 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- MRYQZMHVZZSQRT-UHFFFAOYSA-M tetramethylazanium;acetate Chemical compound CC([O-])=O.C[N+](C)(C)C MRYQZMHVZZSQRT-UHFFFAOYSA-M 0.000 description 1
- ZUEKXCXHTXJYAR-UHFFFAOYSA-N tetrapropan-2-yl silicate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)OC(C)C ZUEKXCXHTXJYAR-UHFFFAOYSA-N 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- GYZQBXUDWTVJDF-UHFFFAOYSA-N tributoxy(methyl)silane Chemical compound CCCCO[Si](C)(OCCCC)OCCCC GYZQBXUDWTVJDF-UHFFFAOYSA-N 0.000 description 1
- OAVPBWLGJVKEGZ-UHFFFAOYSA-N tributoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCCCC)(OCCCC)OCCCC)CCC2OC21 OAVPBWLGJVKEGZ-UHFFFAOYSA-N 0.000 description 1
- FQYWWLSIKWDAEC-UHFFFAOYSA-N tributoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)CCCOCC1CO1 FQYWWLSIKWDAEC-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- VAXCNWCOODGCCT-UHFFFAOYSA-N trichloro-(2-ethoxynaphthalen-1-yl)silane Chemical compound C1=CC=CC2=C([Si](Cl)(Cl)Cl)C(OCC)=CC=C21 VAXCNWCOODGCCT-UHFFFAOYSA-N 0.000 description 1
- QDGORAVIRGNDBW-UHFFFAOYSA-N trichloro-(2-ethoxyphenyl)silane Chemical compound CCOC1=CC=CC=C1[Si](Cl)(Cl)Cl QDGORAVIRGNDBW-UHFFFAOYSA-N 0.000 description 1
- PUOCWUHEMWGXIQ-UHFFFAOYSA-N trichloro-(2-methoxy-2-phenylethyl)silane Chemical compound COC(C[Si](Cl)(Cl)Cl)C1=CC=CC=C1 PUOCWUHEMWGXIQ-UHFFFAOYSA-N 0.000 description 1
- WZLYTTRTHVZCNU-UHFFFAOYSA-N trichloro-(2-methoxynaphthalen-1-yl)silane Chemical compound C1=CC=CC2=C([Si](Cl)(Cl)Cl)C(OC)=CC=C21 WZLYTTRTHVZCNU-UHFFFAOYSA-N 0.000 description 1
- YTWFIHFZPSAMFV-UHFFFAOYSA-N trichloro-(2-methoxyphenyl)silane Chemical compound COC1=CC=CC=C1[Si](Cl)(Cl)Cl YTWFIHFZPSAMFV-UHFFFAOYSA-N 0.000 description 1
- SBNVEGJDYHYOSA-UHFFFAOYSA-N trichloro-(2-propan-2-yloxyphenyl)silane Chemical compound CC(C)OC1=CC=CC=C1[Si](Cl)(Cl)Cl SBNVEGJDYHYOSA-UHFFFAOYSA-N 0.000 description 1
- BXYASSFFTRSIGT-UHFFFAOYSA-N trichloro-[(2-methylpropan-2-yl)oxy-phenylmethyl]silane Chemical compound CC(C)(C)OC([Si](Cl)(Cl)Cl)C1=CC=CC=C1 BXYASSFFTRSIGT-UHFFFAOYSA-N 0.000 description 1
- OUMAYXXJSADQBQ-UHFFFAOYSA-N trichloro-[2-[(2-methylpropan-2-yl)oxy]phenyl]silane Chemical compound CC(C)(C)OC1=CC=CC=C1[Si](Cl)(Cl)Cl OUMAYXXJSADQBQ-UHFFFAOYSA-N 0.000 description 1
- ZZARCDHCAFJWJC-UHFFFAOYSA-N trichloro-[ethoxy(phenyl)methyl]silane Chemical compound CCOC([Si](Cl)(Cl)Cl)C1=CC=CC=C1 ZZARCDHCAFJWJC-UHFFFAOYSA-N 0.000 description 1
- SMGOKIYLLQQVJE-UHFFFAOYSA-N trichloro-[methoxy(phenyl)methyl]silane Chemical compound COC([Si](Cl)(Cl)Cl)C1=CC=CC=C1 SMGOKIYLLQQVJE-UHFFFAOYSA-N 0.000 description 1
- UEUXEIHYBASMLX-UHFFFAOYSA-N trichloro-[phenyl(propan-2-yloxy)methyl]silane Chemical compound CC(C)OC([Si](Cl)(Cl)Cl)C1=CC=CC=C1 UEUXEIHYBASMLX-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- UNKMHLWJZHLPPM-UHFFFAOYSA-N triethoxy(oxiran-2-ylmethoxymethyl)silane Chemical compound CCO[Si](OCC)(OCC)COCC1CO1 UNKMHLWJZHLPPM-UHFFFAOYSA-N 0.000 description 1
- OHKFEBYBHZXHMM-UHFFFAOYSA-N triethoxy-[1-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCO[Si](OCC)(OCC)C(CCC)OCC1CO1 OHKFEBYBHZXHMM-UHFFFAOYSA-N 0.000 description 1
- SJQPASOTJGFOMU-UHFFFAOYSA-N triethoxy-[1-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CCO[Si](OCC)(OCC)C(C)OCC1CO1 SJQPASOTJGFOMU-UHFFFAOYSA-N 0.000 description 1
- NFRRMEMOPXUROM-UHFFFAOYSA-N triethoxy-[1-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)C(CC)OCC1CO1 NFRRMEMOPXUROM-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- FVMMYGUCXRZVPJ-UHFFFAOYSA-N triethoxy-[2-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCO[Si](OCC)(OCC)CC(CC)OCC1CO1 FVMMYGUCXRZVPJ-UHFFFAOYSA-N 0.000 description 1
- RWJUTPORTOUFDY-UHFFFAOYSA-N triethoxy-[2-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CCO[Si](OCC)(OCC)CCOCC1CO1 RWJUTPORTOUFDY-UHFFFAOYSA-N 0.000 description 1
- CFUDQABJYSJIQY-UHFFFAOYSA-N triethoxy-[2-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CC(C)OCC1CO1 CFUDQABJYSJIQY-UHFFFAOYSA-N 0.000 description 1
- NLKPPXKQMJDBFO-UHFFFAOYSA-N triethoxy-[3-(7-oxabicyclo[4.1.0]heptan-4-yl)propyl]silane Chemical compound C1C(CCC[Si](OCC)(OCC)OCC)CCC2OC21 NLKPPXKQMJDBFO-UHFFFAOYSA-N 0.000 description 1
- KPNCYSTUWLXFOE-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCO[Si](OCC)(OCC)CCC(C)OCC1CO1 KPNCYSTUWLXFOE-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- PSUKBUSXHYKMLU-UHFFFAOYSA-N triethoxy-[4-(7-oxabicyclo[4.1.0]heptan-4-yl)butyl]silane Chemical compound C1C(CCCC[Si](OCC)(OCC)OCC)CCC2OC21 PSUKBUSXHYKMLU-UHFFFAOYSA-N 0.000 description 1
- GSUGNQKJVLXBHC-UHFFFAOYSA-N triethoxy-[4-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCCOCC1CO1 GSUGNQKJVLXBHC-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- JOHWNGGYGAVMGU-UHFFFAOYSA-N trifluorochlorine Chemical compound FCl(F)F JOHWNGGYGAVMGU-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 description 1
- LFBULLRGNLZJAF-UHFFFAOYSA-N trimethoxy(oxiran-2-ylmethoxymethyl)silane Chemical compound CO[Si](OC)(OC)COCC1CO1 LFBULLRGNLZJAF-UHFFFAOYSA-N 0.000 description 1
- FFJVMNHOSKMOSA-UHFFFAOYSA-N trimethoxy-[1-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCCC([Si](OC)(OC)OC)OCC1CO1 FFJVMNHOSKMOSA-UHFFFAOYSA-N 0.000 description 1
- DAVVOFDYOGMLNQ-UHFFFAOYSA-N trimethoxy-[1-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CO[Si](OC)(OC)C(C)OCC1CO1 DAVVOFDYOGMLNQ-UHFFFAOYSA-N 0.000 description 1
- FNBIAJGPJUOAPB-UHFFFAOYSA-N trimethoxy-[1-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)C(CC)OCC1CO1 FNBIAJGPJUOAPB-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- ZNXDCSVNCSSUNB-UHFFFAOYSA-N trimethoxy-[2-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CO[Si](OC)(OC)CCOCC1CO1 ZNXDCSVNCSSUNB-UHFFFAOYSA-N 0.000 description 1
- HTVULPNMIHOVRU-UHFFFAOYSA-N trimethoxy-[2-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CC(C)OCC1CO1 HTVULPNMIHOVRU-UHFFFAOYSA-N 0.000 description 1
- DBUFXGVMAMMWSD-UHFFFAOYSA-N trimethoxy-[3-(7-oxabicyclo[4.1.0]heptan-4-yl)propyl]silane Chemical compound C1C(CCC[Si](OC)(OC)OC)CCC2OC21 DBUFXGVMAMMWSD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- ZOWVSEMGATXETK-UHFFFAOYSA-N trimethoxy-[4-(7-oxabicyclo[4.1.0]heptan-4-yl)butyl]silane Chemical compound C1C(CCCC[Si](OC)(OC)OC)CCC2OC21 ZOWVSEMGATXETK-UHFFFAOYSA-N 0.000 description 1
- GUKYSRVOOIKHHB-UHFFFAOYSA-N trimethoxy-[4-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CO[Si](OC)(OC)CCCCOCC1CO1 GUKYSRVOOIKHHB-UHFFFAOYSA-N 0.000 description 1
- NBNZEBUNZGWIRJ-UHFFFAOYSA-N triphenylsulfanium;nitrate Chemical compound [O-][N+]([O-])=O.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 NBNZEBUNZGWIRJ-UHFFFAOYSA-N 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- XMUJIPOFTAHSOK-UHFFFAOYSA-N undecan-2-ol Chemical compound CCCCCCCCCC(C)O XMUJIPOFTAHSOK-UHFFFAOYSA-N 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
Classifications
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- 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
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
- G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
- H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
- H01L21/0274—Photolithographic processes
- H01L21/0276—Photolithographic processes using an anti-reflective coating
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- 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
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/16—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers in which all the silicon atoms are connected by linkages other than oxygen atoms
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- 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
- G03F1/00—Originals for photomechanical production of textured or patterned surfaces, e.g., masks, photo-masks, reticles; Mask blanks or pellicles therefor; Containers specially adapted therefor; Preparation thereof
- G03F1/68—Preparation processes not covered by groups G03F1/20 - G03F1/50
- G03F1/80—Etching
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- 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
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0042—Photosensitive materials with inorganic or organometallic light-sensitive compounds not otherwise provided for, e.g. inorganic resists
- G03F7/0043—Chalcogenides; Silicon, germanium, arsenic or derivatives thereof; Metals, oxides or alloys thereof
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- 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
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- 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
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
- G03F7/0752—Silicon-containing compounds in non photosensitive layers or as additives, e.g. for dry lithography
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
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Abstract
Description
第2観点として、カルボニル基含有官能基を含む単位構造が、環状酸無水物基、環状ジエステル基、又はジエステル基を含む単位構造である第1観点に記載のシリコン含有レジスト下層膜形成組成物、
第3観点として、上記ポリシロキサンが、下記式(1)で表されるシランを含む加水分解性シランの加水分解縮合物である第1観点に記載のシリコン含有レジスト下層膜形成組成物、
式(1):
式(1)中R2はアルキル基、アリール基、ハロゲン化アルキル基、ハロゲン化アリール基、アルケニル基、又はエポキシ基、アクリロイル基、メタクリロイル基、メルカプト基、アミノ基、もしくはシアノ基を有する有機基で且つSi−C結合によりケイ素原子と結合しているものである。
式(1)中R3はアルコキシ基、アシルオキシ基、又はハロゲン原子を示す。aは1の整数を示し、bは0又は1の整数を示し、a+bは1又は2の整数を示す。]
第4観点として、上記ポリシロキサンが、更にアミド基含有有機基を含む単位構造を含む第1観点又は第2観点に記載のシリコン含有レジスト下層膜形成組成物、
第5観点として、アミド基が、スルホンアミド基、又はジアリルイソシアヌレート基である第4観点に記載のシリコン含有レジスト下層膜形成組成物、
第6観点として、上記ポリシロキサンが、上記式(1)で表されるシラン及び下記式(2)で表されるシランを含む加水分解性シランの共加水分解縮合物である第1観点に記載のシリコン含有レジスト下層膜形成組成物、
式(2):
式(2)中R5はアルキル基、アリール基、ハロゲン化アルキル基、ハロゲン化アリール基、アルケニル基、又はエポキシ基、アクリロイル基、メタクリロイル基、メルカプト基、アミノ基、もしくはシアノ基を有する有機基で且つSi−C結合によりケイ素原子と結合しているものである。
式(2)中R6はアルコキシ基、アシルオキシ基、又はハロゲン原子を示す。aは1の整数を示し、bは0又は1の整数を示し、a+bは1又は2の整数を示す。※は直接または連結基を通じてシリコン原子との結合部位である。]、
第7観点として、上記ポリシロキサンが、上記式(1)で表されるシランと上記式(2)で表されるシランとその他のシランを含む加水分解性シランの共加水分解縮合物であり、その他のシランが式(3)で表されるシラン及び式(4)で表されるシランからなる群より選ばれた少なくとも1種のシランである請求項1に記載のシリコン含有レジスト下層膜形成組成物、
第8観点として、更に光酸発生剤を含む第1観点乃至第7観点のいずれか一つに記載のシリコン含有レジスト下層膜形成組成物、
第9観点として、更に金属酸化物を含む第1観点乃至第8観点のいずれか一つに記載のシリコン含有レジスト下層膜形成組成物、
第10観点として、上記過酸化水素を含む薬液が、アンモニアと過酸化水素を含む水溶液、塩酸と過酸化水素を含む水溶液、硫酸と過酸化水素を含む水溶液、又は弗酸と過酸化水素を含む水溶液である第1観点乃至第9観点のいずれか一つに記載のシリコン含有レジスト下層膜形成組成物、
第11観点として、第1観点乃至第10観点のいずれか一つに記載のレジスト下層膜形成組成物を半導体基板上に塗布し焼成することによって得られるレジスト下層膜の製造方法、
第12観点として、第1観点乃至第10観点のいずれか一つに記載のレジスト下層膜形成組成物を半導体基板上に塗布し、焼成しレジスト下層膜を形成する工程、前記下層膜の上にレジスト用組成物を塗布しレジスト膜を形成する工程、前記レジスト膜を露光する工程、露光後にレジストを現像しレジストパターンを得る工程、レジストパターンによりレジスト下層膜をエッチングする工程、及びパターン化されたレジストとレジスト下層膜により半導体基板を加工する工程、マスク層を過酸化水素を含む薬液で除去する工程を含む半導体装置の製造方法、
第13観点として、半導体基板上に有機下層膜を形成する工程、その上に第1観点乃至第10観点のいずれか一つに記載のレジスト下層膜形成組成物を塗布し焼成しレジスト下層膜を形成する工程、前記レジスト下層膜の上にレジスト用組成物を塗布しレジスト層を形成する工程、前記レジスト膜を露光する工程、露光後にレジストを現像しレジストパターンを得る工程、レジストパターンによりレジスト下層膜をエッチングする工程、パターン化されたレジスト下層膜により有機下層膜をエッチングする工程、及びパターン化された有機下層膜により半導体基板を加工する工程、マスク層を過酸化水素を含む薬液で除去する工程を含む半導体装置の製造方法、
第14観点として、上記基板の加工が、エッチング、又はイオン注入である第12観点又は第13観点に記載の半導体装置の製造方法、及び
第15観点として、マスク層が、レジスト又はレジスト下層膜を含む有機下層膜である第12観点乃至第13観点のいずれか一つに記載の半導体装置の製造方法である。
加水分解縮合物を得る際に加水分解が完全に完了しない部分加水分解物やシラン化合物が加水分解縮合物に混合されて、その混合物を用いることもできる。この縮合物はポリシロキサン構造を有するポリマーである。
式中R1は上記式(1−1)、式(1−2)、式(1−3)、式(1−4)、式(1−5)、又は式(1−6)を含む有機基であり、且つSi−C結合によりケイ素原子と結合しているものである。
式(1−4)、式(1−5)、式(1−6)中で、T11、T15、及びT18はアルキレン基、環状アルキレン基、アルケニレン基、アリーレン基、イオウ原子、酸素原子、オキシカルボニル基、アミド基、2級アミノ基、又はそれらの組み合わせであり、T12、T13、T14、T16、T17、T19及びT20はそれぞれ水素原子又はアルキル基であり、T21はアルキレン基である。
またこれらのフッ素、塩素、臭素、又はヨウ素等のハロゲン原子が置換した有機基が挙げられる。
加水分解し縮合させる際に触媒を用いることができる。
式(D−3):
式(D−4):
式(D−5):
式(D−6):
また、ホスホニウム塩としては、式(D−7):
また、スルホニウム塩としては、式(D−8):
酸発生剤としては、熱酸発生剤や光酸発生剤が挙げられる。
光酸発生剤は、レジストの露光時に酸を生ずる。そのため、下層膜の酸性度の調整ができる。これは、下層膜の酸性度を上層のレジストとの酸性度に合わせるための一方法である。また、下層膜の酸性度の調整によって、上層に形成されるレジストのパターン形状の調整ができる。
基板の加工後にマスク層が過酸化水素を含む薬液で除去する工程を経て半導体装置が製造される。マスク層はレジスト又はレジスト下層膜を含む有機下層膜である。
テトラエトキシシラン20.0g、フェニルトリメトキシシラン1.5g、5−(トリエトキシシリル)ヘキサヒドロ−4,7−メタノイソベンゾフラン−1,3−ジオン14.6g、アセトン54.2gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01M塩酸水溶液9.7gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、240分間、還流させた。その後、プロピレングリコールモノメチルエーテルアセテート72gを加え、アセトン、メタノール、エタノール、水を減圧留去し、濃縮して加水分解縮合物(ポリマー)水溶液を得た。さらにプロピレングリコールモノエチルエーテルを加え、プロピレングリコールモノエチルエーテル80%プロピレングリコールモノメチルエーテルアセテート20%の溶媒比率として140℃における固形残物換算で13質量パーセントとなるように調整した。得られたポリマーは式(3−1)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1500であった。
テトラエトキシシラン20.0g、フェニルトリメトキシシラン1.5g、5−(トリエトキシシリル)ヘキサヒドロ−4,7−メタノイソベンゾフラン−1,3−ジオン14.6g、アセトン54.2gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01M塩酸水溶液9.7gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、240分間、還流させた。その後、プロピレングリコールモノメチルエーテルアセテート72gを加え、アセトン、メタノール、エタノール、水を減圧留去し、濃縮して加水分解縮合物(ポリマー)水溶液を得た。さらにプロピレングリコールモノメチルエーテルを加え、140℃における固形残物換算で13質量パーセントとなるように調整した。得られたポリマーは式(3−1)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1500であった。
テトラエトキシシラン19.3g、フェニルトリメトキシシラン1.4g、2,2,5−トリメチル−5−(3−(トリエトキシシリル)プロピル)−1,3−ジオキサン−4,6−ジオン15.5g、アセトン54.4gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01M塩酸水溶液9.4gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、240分間、還流させた。その後、プロピレングリコールモノメチルエーテルアセテート72gを加え、アセトン、メタノール、エタノール、水を減圧留去し、濃縮して加水分解縮合物(ポリマー)水溶液を得た。さらにプロピレングリコールモノエチルエーテルアセテートを加え、プロピレングリコールモノエチルエーテル80%プロピレングリコールモノメチルエーテルアセテート20%の溶媒比率として140℃における固形残物換算で13質量パーセントとなるように調整した。得られたポリマーは式(3−2)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1500であった。
テトラエトキシシラン18.2g、フェニルトリメトキシシラン1.3g、ジターシャルブチル2−(3−(トリエトキシシリル)プロピル)マロネート16.9g、アセトン54.4gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01M塩酸水溶液8.8gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、240分間、還流させた。その後、プロピレングリコールモノメチルエーテルアセテート72gを加え、アセトン、メタノール、エタノール、水を減圧留去し、濃縮して加水分解縮合物(ポリマー)水溶液を得た。さらにプロピレングリコールモノエチルエーテルを加え、プロピレングリコールモノエチルエーテル80%プロピレングリコールモノメチルエーテルアセテート20%の溶媒比率として140℃における固形残物換算で13質量パーセントとなるように調整した。得られたポリマーは式(3−3)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1500であった。
テトラエトキシシラン20.6g、フェニルトリメトキシシラン1.5g、3−(3−(トリエトキシシリル)プロピル)ジヒドロフラン−2,5−ジオン13.9g、アセトン54.0gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01M塩酸水溶液10.0gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、240分間、還流させた。その後、プロピレングリコールモノメチルエーテルアセテート72gを加え、アセトン、メタノール、エタノール、水を減圧留去し、濃縮して加水分解縮合物(ポリマー)水溶液を得た。さらにプロピレングリコールモノエチルエーテルを加え、プロピレングリコールモノエチルエーテル80%プロピレングリコールモノメチルエーテルアセテート20%の溶媒比率として140℃における固形残物換算で13質量パーセントとなるように調整した。得られたポリマーは式(3−4)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1500であった。
テトラエトキシシラン24.1g、フェニルトリメトキシシラン1.6g、トリエトキシメチルシラン4.42g、5−(トリエトキシシリル)ヘキサヒドロ−4,7−メタノイソベンゾフラン−1,3−ジオン5.4g、アセトン53.4gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01M塩酸水溶液11.0gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、240分間、還流させた。その後、プロピレングリコールモノメチルエーテル72gを加え、アセトン、メタノール、エタノール、水を減圧留去し、濃縮して加水分解縮合物(ポリマー)水溶液を得た。さらにプロピレングリコールモノメチルエーテルを加え、140℃における固形残物換算で13質量パーセントとなるように調整した。得られたポリマーは式(3−5)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1500であった。
テトラエトキシシラン12.1g、フェニルトリメトキシシラン1.3g、2,2,5−トリメチル−5−(3−(トリエトキシシリル)プロピル)−1,3−ジオキサン−4,6−ジオン23.4g、アセトン55.2gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01M塩酸水溶液8.0gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、240分間、還流させた。その後、プロピレングリコールモノメチルエーテル74gを加え、アセトン、メタノール、エタノール、水を減圧留去し、濃縮して加水分解縮合物(ポリマー)水溶液を得た。さらにプロピレングリコールモノメチルエーテルを加え、140℃における固形残物換算で13質量パーセントとなるように調整した。得られたポリマーは式(3−2)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1500であった。
テトラエトキシシラン19.5g、5−(トリエトキシシリル)ヘキサヒドロ−4,7−メタノイソベンゾフラン−1,3−ジオン14.2g、フェニルスルホニルアミドプロピルトリエトキシシラン2.6g、アセトン54.3gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01M塩酸水溶液9.5gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、240分間、還流させた。その後、プロピレングリコールモノメチルエーテル72gを加え、アセトン、メタノール、エタノール、水を減圧留去し、濃縮して加水分解縮合物(ポリマー)水溶液を得た。さらにプロピレングリコールモノメチルエーテルを加え、140℃における固形残物換算で13質量パーセントとなるように調整した。得られたポリマーは式(3−6)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1500であった。
テトラエトキシシラン17.2g、5−(トリエトキシシリル)ヘキサヒドロ−4,7−メタノイソベンゾフラン−1,3−ジオン13.6g、ジアリルイソシアネートプロピルトリエトキシシラン5.7g、アセトン54.7gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01M塩酸水溶液8.9gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、240分間、還流させた。その後、プロピレングリコールモノメチルエーテル72gを加え、アセトン、メタノール、エタノール、水を減圧留去し、濃縮して加水分解縮合物(ポリマー)水溶液を得た。さらにプロピレングリコールモノメチルエーテルを加え、140℃における固形残物換算で13質量パーセントとなるように調整した。得られたポリマーは式(3−7)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1500であった。
テトラエトキシシラン24.1g、フェニルトリメトキシシラン1.8g、トリエトキシメチルシラン9.5g、アセトン53.0gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01M塩酸水溶液11.7gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、240分間、還流させた。その後、プロピレングリコールモノメチルエーテル70gを加え、アセトン、メタノール、エタノール、水を減圧留去し、濃縮して加水分解縮合物(ポリマー)水溶液を得た。さらにプロピレングリコールモノメチルエーテルを加え、140℃における固形残物換算で13質量パーセントとなるように調整した。得られたポリマーは式(4−1)に相当し、GPCによる重量平均分子量はポリスチレン換算でMw1400であった。
上記合成例1乃至合成例9、比較合成例1で得られたケイ素含有ポリマー、酸、溶媒を表1に示す割合で混合し、0.1μmのフッ素樹脂製のフィルターで濾過することによって、ポリマー含有塗布液をそれぞれ調製した。表1中のポリマーの添加割合はポリマー溶液の添加量ではなく、ポリマー自体の添加量を示した。
窒素下、100mL四口フラスコにカルバゾール(6.69g、0.040mol、東京化成工業(株)製)、9−フルオレノン(7.28g、0.040mol、東京化成工業(株)製)、パラトルエンスルホン酸一水和物(0.76g、0.0040mol、東京化成工業(株)製)を加え、1,4−ジオキサン(6.69g、関東化学(株)製)を仕込み撹拌し、100℃まで昇温し溶解させ重合を開始した。24時間後60℃まで放冷後、クロロホルム(34g、関東化学(株)製)を加え希釈し、メタノール(168g、関東化学(株)製)へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で80℃、24時間乾燥し、目的とするポリマー(式(5−1)、以下PCzFLと略す)9.37gを得た。
1H−NMR(400MHz,DMSO−d6):δ7.03−7.55(br,12H),δ7.61−8.10(br,4H),δ11.18(br,1H)
PCzFLのGPCによるポリスチレン換算で測定される重量平均分子量Mwは2800、多分散度Mw/Mnは1.77であった。
得られた樹脂20gに、架橋剤としてテトラメトキシメチルグリコールウリル(三井サイテック(株)製、商品名パウダーリンク1174)3.0g、触媒としてピリジニウムパラトルエンスルホネート0.30g、界面活性剤としてメガファックR−30(大日本インキ化学(株)製、商品名)0.06gを混合し、プロピレングリコールモノメチルエーテルアセテート88gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いる有機下層膜(A層)形成組成物の溶液を調製した。
<レジストパターニング評価:アルカリ現像を行うPTD工程を経由した評価>
上記式で得られた有機下層膜(A層)形成組成物をシリコンウエハー上に塗布し、ホットプレート上で240℃、60秒間ベークし、膜厚200nmの有機下層膜(A層)を得た。その上に、実施例3,実施例4,実施例6乃至実施例10、比較例1で得られたSi含有レジスト下層膜(B層)形成組成物を塗布し、ホットプレート上で180℃、60秒間ベークし、Si含有レジスト下層膜(B層)を得た。Si含有レジスト下層膜(B層)の膜厚は40nmであった。
B層の上に市販のArF用レジスト溶液(JSR(株)製、商品名:AR2772JN)をスピナーによりそれぞれ塗布し、ホットプレート上で110℃にて1分間加熱し、膜厚120nmのフォトレジスト膜(C層)を形成した。
(株)ニコン製NSR−S307Eスキャナー(波長193nm、NA、σ:0.85、0.93/0.85)を用い、現像後にフォトレジストのライン幅及びそのライン間の幅が0.062μm、すなわち0.062μmのラインアンドスペース(L/S)=1/1のデンスラインが形成されるように設定されたマスクにそれぞれを通して露光を行った。その後、ホットプレート上100℃で60秒間ベークし、冷却後、2.38%アルカリ水溶液を用いて60秒現像し、レジスト下層膜(B層)上にポジ型のパターンを形成した。得られたフォトレジストパターンについて、大きなパターン剥がれやアンダーカット、ライン底部の太り(フッティング)が発生しないものを良好として評価した。
<レジストパターニング評価:溶剤現像を行うNTD工程を経由した評価>
上記式で得られた有機下層膜(A層)形成組成物をシリコンウエハー上に塗布し、ホットプレート上で240℃で60秒間ベークし、膜厚200nmの有機下層膜(A層)を得た。その上に、実施例1乃至実施例7、比較例1で得られたSi含有レジスト下層膜(B層)形成組成物を塗布し、ホットプレート上で180℃で60秒間ベークし、Si含有レジスト下層膜(B層)を得た。Si含有レジスト下層膜(B層)の膜厚は40nmであった。
B層の上に市販のフォトレジスト溶液(富士フイルム(株)製、商品名FAiRS−9521NT05)をスピナーによりそれぞれ塗布し、ホットプレート上で100℃にて1分間加熱し、膜厚85nmのフォトレジスト膜(C層)を形成した。
(株)ニコン製NSR−S307Eスキャナー(波長193nm、NA、σ:0.85、0.93/0.85)を用い、現像後にフォトレジストのライン幅及びそのライン間の幅が0.062μm、すなわち0.062μmのラインアンドスペース(L/S)=1/1のデンスラインが形成されるように設定されたマスクにそれぞれを通して露光を行った。その後、ホットプレート上100℃で60秒間ベークし、冷却後、2.38%アルカリ水溶液を用いて60秒現像し、レジスト下層膜(B層)上にポジ型のパターンを形成した。得られたフォトレジストパターンについて、大きなパターン剥がれやアンダーカット、ライン底部の太り(フッティング)が発生しないものを良好として評価した。
実施例1乃至実施例10、比較例1で調製したSi含有塗布液をスピナーを用い、シリコンウェハー上に塗布した。ホットプレート上で180℃1分間加熱し、Si含有レジスト下層膜をそれぞれ形成した。その後、60℃に調整したSC−1薬液(28%アンモニア水/33%過酸化水素水/水=1/1/40)をSi含有レジスト下層膜上に3分間塗布、1分間水リンス、さらに30秒スピン乾燥し、溶剤塗布前後での膜厚の変化の有無を評価した。膜厚変化が90%以上のものを「良好」、膜厚変化が90%以下のものを「溶解せず」とした。
実施例1乃至実施例10、比較例1で調製したSi含有塗布液をスピナーを用い、シリコンウェハー上に塗布した。ホットプレート上で180℃1分間加熱し、Si含有レジスト下層膜をそれぞれ形成した。その後、サムコ製ドライエッチャー(RIE-10NR)を用いて、酸素エッチングを5秒行った。その後、60℃に調整したSC−1薬液(28%アンモニア水/33%過酸化水素水/水=1/1/40)をSi含有レジスト下層膜上に3分間塗布、1分間水リンス、さらに30秒スピン乾燥し、溶剤塗布前後での膜厚の変化の有無を評価した。膜厚変化が90%以上のものを「良好」、膜厚変化が90%以下のものを「溶解せず」とした。
Claims (15)
- シリコン含有レジスト下層膜を形成するための組成物であって、該シリコン含有レジスト下層膜は、リソグラフィープロセスでパターンを下層に転写した後に過酸化水素を含む薬液でマスク層の除去を行う工程において該マスク層として使用される膜であり、前記組成物は、カルボニル基含有官能基を含む単位構造を含むポリシロキサンを含むことを特徴とするシリコン含有レジスト下層膜形成組成物。
- カルボニル基含有官能基を含む単位構造が、環状酸無水物基、環状ジエステル基、又はジエステル基を含む単位構造である請求項1に記載のシリコン含有レジスト下層膜形成組成物。
- 前記ポリシロキサンが、下記式(1)で表されるシランを含む加水分解性シランの加水分解縮合物である請求項1に記載のシリコン含有レジスト下層膜形成組成物。
式(1):
式(1)中R2はアルキル基、アリール基、ハロゲン化アルキル基、ハロゲン化アリール基、アルケニル基、又はエポキシ基、アクリロイル基、メタクリロイル基、メルカプト基、アミノ基、もしくはシアノ基を有する有機基で且つSi−C結合によりケイ素原子と結合しているものである。
式(1)中R3はアルコキシ基、アシルオキシ基、又はハロゲン原子を示す。aは1の整数を示し、bは0又は1の整数を示し、a+bは1又は2の整数を示す。] - 前記ポリシロキサンが、更にアミド基含有有機基を含む単位構造を含む請求項1又は請求項2に記載のシリコン含有レジスト下層膜形成組成物。
- アミド基が、スルホンアミド基、又はジアリルイソシアヌレート基である請求項4に記載のシリコン含有レジスト下層膜形成組成物。
- 前記ポリシロキサンが、前記式(1)で表されるシラン及び下記式(2)で表されるシランを含む加水分解性シランの共加水分解縮合物である請求項1に記載のシリコン含有レジスト下層膜形成組成物。
式(2):
式(2)中R5はアルキル基、アリール基、ハロゲン化アルキル基、ハロゲン化アリール基、アルケニル基、又はエポキシ基、アクリロイル基、メタクリロイル基、メルカプト基、アミノ基、もしくはシアノ基を有する有機基で且つSi−C結合によりケイ素原子と結合しているものである。
式(2)中R6はアルコキシ基、アシルオキシ基、又はハロゲン原子を示す。aは1の整数を示し、bは0又は1の整数を示し、a+bは1又は2の整数を示す。※は直接または連結基を通じてシリコン原子との結合部位である。] - 前記ポリシロキサンが、前記式(1)で表されるシランと前記式(2)で表されるシランとその他のシランを含む加水分解性シランの共加水分解縮合物であり、その他のシランが式(3)で表されるシラン及び式(4)で表されるシランからなる群より選ばれた少なくとも1種のシランである請求項1に記載のシリコン含有レジスト下層膜形成組成物。
- 更に光酸発生剤を含む請求項1乃至請求項7のいずれか1項に記載のシリコン含有レジスト下層膜形成組成物。
- 更に金属酸化物を含む請求項1乃至請求項8のいずれか1項に記載のシリコン含有レジスト下層膜形成組成物。
- 前記過酸化水素を含む薬液が、アンモニアと過酸化水素を含む水溶液、塩酸と過酸化水素を含む水溶液、硫酸と過酸化水素を含む水溶液、又は弗酸と過酸化水素を含む水溶液である請求項1乃至請求項9のいずれか1項に記載のシリコン含有レジスト下層膜形成組成物。
- 請求項1乃至請求項10のいずれか1項に記載のレジスト下層膜形成組成物を半導体基板上に塗布し焼成することによって得られるレジスト下層膜の製造方法。
- 請求項1乃至請求項10のいずれか1項に記載のレジスト下層膜形成組成物を半導体基板上に塗布し、焼成しレジスト下層膜を形成する工程、前記下層膜の上にレジスト用組成物を塗布しレジスト膜を形成する工程、前記レジスト膜を露光する工程、露光後にレジストを現像しレジストパターンを得る工程、レジストパターンによりレジスト下層膜をエッチングする工程、及びパターン化されたレジストとレジスト下層膜により半導体基板を加工する工程、マスク層を過酸化水素を含む薬液で除去する工程を含む半導体装置の製造方法。
- 半導体基板上に有機下層膜を形成する工程、その上に請求項1乃至請求項10のいずれか1項に記載のレジスト下層膜形成組成物を塗布し焼成しレジスト下層膜を形成する工程、前記レジスト下層膜の上にレジスト用組成物を塗布しレジスト層を形成する工程、前記レジスト膜を露光する工程、露光後にレジストを現像しレジストパターンを得る工程、レジストパターンによりレジスト下層膜をエッチングする工程、パターン化されたレジスト下層膜により有機下層膜をエッチングする工程、及びパターン化された有機下層膜により半導体基板を加工する工程、マスク層を過酸化水素を含む薬液で除去する工程を含む半導体装置の製造方法。
- 前記基板の加工が、エッチング、又はイオン注入である請求項12又は請求項13に記載の半導体装置の製造方法。
- マスク層が、レジスト又はレジスト下層膜を含む有機下層膜である請求項12乃至請求項13のいずれか1項に記載の半導体装置の製造方法。
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JP7307004B2 (ja) * | 2019-04-26 | 2023-07-11 | 信越化学工業株式会社 | ケイ素含有レジスト下層膜形成用組成物及びパターン形成方法 |
WO2021221171A1 (ja) | 2020-04-30 | 2021-11-04 | 日産化学株式会社 | レジスト下層膜形成用組成物 |
KR20230112660A (ko) | 2020-11-27 | 2023-07-27 | 닛산 가가쿠 가부시키가이샤 | 실리콘 함유 레지스트 하층막 형성용 조성물 |
WO2022210901A1 (ja) * | 2021-03-31 | 2022-10-06 | 日産化学株式会社 | シリコン含有レジスト下層膜形成用組成物 |
US20230012705A1 (en) * | 2021-07-16 | 2023-01-19 | Taiwan Semiconductor Manufacturing Co., Ltd. | Humidity control or aqueous treatment for euv metallic resist |
CN118159910A (zh) * | 2021-10-28 | 2024-06-07 | 日产化学株式会社 | 含添加剂含硅抗蚀剂下层膜形成组合物 |
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