WO2022230940A1 - シリコン含有レジスト下層膜形成用組成物 - Google Patents
シリコン含有レジスト下層膜形成用組成物 Download PDFInfo
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- WO2022230940A1 WO2022230940A1 PCT/JP2022/019102 JP2022019102W WO2022230940A1 WO 2022230940 A1 WO2022230940 A1 WO 2022230940A1 JP 2022019102 W JP2022019102 W JP 2022019102W WO 2022230940 A1 WO2022230940 A1 WO 2022230940A1
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- underlayer film
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- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- LTWFAYWMPMMDGT-UHFFFAOYSA-N tert-butyl 3-oxohexaneperoxoate;titanium Chemical compound [Ti].CCCC(=O)CC(=O)OOC(C)(C)C.CCCC(=O)CC(=O)OOC(C)(C)C LTWFAYWMPMMDGT-UHFFFAOYSA-N 0.000 description 1
- NVQCTSGVFRPZCZ-UHFFFAOYSA-N tert-butyl 3-oxohexaneperoxoate;zirconium Chemical compound [Zr].CCCC(=O)CC(=O)OOC(C)(C)C.CCCC(=O)CC(=O)OOC(C)(C)C NVQCTSGVFRPZCZ-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003866 tertiary ammonium salts Chemical class 0.000 description 1
- 238000012360 testing method Methods 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
- DFQPZDGUFQJANM-UHFFFAOYSA-M tetrabutylphosphanium;hydroxide Chemical compound [OH-].CCCC[P+](CCCC)(CCCC)CCCC DFQPZDGUFQJANM-UHFFFAOYSA-M 0.000 description 1
- BRGJIIMZXMWMCC-UHFFFAOYSA-N tetradecan-2-ol Chemical compound CCCCCCCCCCCCC(C)O BRGJIIMZXMWMCC-UHFFFAOYSA-N 0.000 description 1
- 229940072958 tetrahydrofurfuryl oleate Drugs 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
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- ZEMGGZBWXRYJHK-UHFFFAOYSA-N thiouracil Chemical compound O=C1C=CNC(=S)N1 ZEMGGZBWXRYJHK-UHFFFAOYSA-N 0.000 description 1
- 229950000329 thiouracil Drugs 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- YZVRVDPMGYFCGL-UHFFFAOYSA-N triacetyloxysilyl acetate Chemical compound CC(=O)O[Si](OC(C)=O)(OC(C)=O)OC(C)=O YZVRVDPMGYFCGL-UHFFFAOYSA-N 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
- FMYXZXAKZWIOHO-UHFFFAOYSA-N trichloro(2-phenylethyl)silane Chemical compound Cl[Si](Cl)(Cl)CCC1=CC=CC=C1 FMYXZXAKZWIOHO-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
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- HKFSBKQQYCMCKO-UHFFFAOYSA-N trichloro(prop-2-enyl)silane Chemical compound Cl[Si](Cl)(Cl)CC=C HKFSBKQQYCMCKO-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
- 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
- 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
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
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- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
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- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-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
- 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
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- UBMUZYGBAGFCDF-UHFFFAOYSA-N trimethoxy(2-phenylethyl)silane Chemical compound CO[Si](OC)(OC)CCC1=CC=CC=C1 UBMUZYGBAGFCDF-UHFFFAOYSA-N 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
- HGCVEHIYVPDFMS-UHFFFAOYSA-N trimethoxy(7-oxabicyclo[4.1.0]heptan-4-ylmethyl)silane Chemical compound C1C(C[Si](OC)(OC)OC)CCC2OC21 HGCVEHIYVPDFMS-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
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-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
- 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
- ZQPNGHDNBNMPON-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CO[Si](OC)(OC)CCC(C)OCC1CO1 ZQPNGHDNBNMPON-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
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- HADKRTWCOYPCPH-UHFFFAOYSA-M trimethylphenylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C1=CC=CC=C1 HADKRTWCOYPCPH-UHFFFAOYSA-M 0.000 description 1
- MDTPTXSNPBAUHX-UHFFFAOYSA-M trimethylsulfanium;hydroxide Chemical compound [OH-].C[S+](C)C MDTPTXSNPBAUHX-UHFFFAOYSA-M 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- XZZGCKRBJSPNEF-UHFFFAOYSA-M triphenylsulfanium;acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 XZZGCKRBJSPNEF-UHFFFAOYSA-M 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- MKZVNKSVBFCDLB-UHFFFAOYSA-M tris(2-tert-butylphenyl)sulfanium;hydroxide Chemical compound [OH-].CC(C)(C)C1=CC=CC=C1[S+](C=1C(=CC=CC=1)C(C)(C)C)C1=CC=CC=C1C(C)(C)C MKZVNKSVBFCDLB-UHFFFAOYSA-M 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- XMUJIPOFTAHSOK-UHFFFAOYSA-N undecan-2-ol Chemical compound CCCCCCCCCC(C)O XMUJIPOFTAHSOK-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- G03F7/09—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
-
- 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
-
- 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
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
- H01L21/306—Chemical or electrical treatment, e.g. electrolytic etching
-
- 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
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
- H01L21/306—Chemical or electrical treatment, e.g. electrolytic etching
- H01L21/30604—Chemical etching
-
- 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
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
- H01L21/306—Chemical or electrical treatment, e.g. electrolytic etching
- H01L21/3065—Plasma etching; Reactive-ion etching
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- 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
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
- H01L21/306—Chemical or electrical treatment, e.g. electrolytic etching
- H01L21/308—Chemical or electrical treatment, e.g. electrolytic etching using masks
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
Definitions
- the present invention relates to a composition for forming a silicon-containing resist underlayer film.
- Microfabrication by lithography using a photoresist has been conventionally performed in the manufacture of semiconductor devices.
- Microfabrication involves forming a thin film of photoresist on a semiconductor substrate such as a silicon wafer, irradiating it with actinic rays such as ultraviolet rays through a mask pattern on which a semiconductor device pattern is drawn, and developing it.
- actinic rays such as ultraviolet rays
- This is a processing method in which fine unevenness corresponding to the pattern is formed on the surface of the substrate by etching the substrate using a photoresist pattern as a protective film.
- a film known as a hard mask containing metal elements such as silicon and titanium is used as an underlayer film between the semiconductor substrate and the photoresist.
- the resist and the hard mask have large differences in their constituent components, their removal rate by dry etching greatly depends on the type of gas used for dry etching. By appropriately selecting the gas species, the hard mask can be removed by dry etching without significantly reducing the film thickness of the photoresist.
- a resist underlayer film has been placed between the semiconductor substrate and the photoresist in order to achieve various effects including an antireflection effect.
- compositions for resist underlayer films have been studied so far, the development of new materials for resist underlayer films is desired due to the diversity of required properties.
- coating-type BPSG (boron phosphorous glass) film-forming composition containing a structure having a specific silicic acid skeleton Patent Document 1
- Patent Document 2 A composition for forming a silicon-containing resist underlayer film containing a carbonyl structure (Patent Document 2) is disclosed for the purpose of removing a chemical solution.
- the present invention has been made in view of such circumstances, and removes not only the conventional dry etching method but also the wet etching method using a chemical solution (wet method) in the process of processing a semiconductor substrate or the like.
- a composition for forming a silicon-containing resist underlayer film for forming a resist underlayer film capable of forming a resist underlayer film capable of forming a resist underlayer film particularly silicon for forming a resist underlayer film having excellent lithography properties and realizing a high etching rate in wet etching.
- An object of the present invention is to provide a composition for forming an underlayer film containing
- the present invention includes the following.
- the mass ratio of the [D] component to the [B] component ([D]:[B]) is 0.1:1.0 to 1.0:0.1
- [6] The silicon-containing resist underlayer according to any one of [1] to [5], wherein the component [A] contains a modified polysiloxane in which at least part of the silanol groups are alcohol-modified or acetal-protected. Film-forming composition.
- component [C] contains propylene glycol monoalkyl ether.
- Component [E] The composition for forming a silicon-containing resist underlayer film according to any one of [1] to [8], further containing nitric acid.
- Component [F] The composition for forming a silicon-containing resist underlayer film according to any one of [1] to [9], further containing at least one selected from amines and hydroxides.
- a semiconductor processing substrate comprising a semiconductor substrate and the resist underlayer film according to [13].
- [15] forming an organic underlayer film on a substrate; forming a resist underlayer film on the organic underlayer film using the composition for forming a silicon-containing resist underlayer film according to any one of [1] to [12]; forming a resist film on the resist underlayer film;
- a method of manufacturing a semiconductor device comprising: [16] In the step of forming the resist underlayer film, a composition for forming a silicon-containing resist underlayer film that has been filtered through a nylon filter is used. [15] The method for manufacturing a semiconductor device according to [15].
- [17] forming an organic underlayer film on a semiconductor substrate; a step of applying the silicon-containing resist underlayer film-forming composition according to any one of [1] to [12] onto the organic underlayer film and baking the composition to form a resist underlayer film; a step of applying a composition for forming a resist film on the resist underlayer film to form a resist film; exposing and developing the resist film to obtain a resist pattern; Etching the resist underlayer film using the resist pattern as a mask; using the patterned resist underlayer film as a mask to etch the organic underlayer film; A method of forming a pattern, comprising: [18] removing the silicon-containing resist underlayer film by a wet method using a chemical after the step of etching the organic underlayer film; The pattern forming method according to [17], further comprising
- silicon can be removed not only by a conventional dry etching method but also by a wet etching method using a chemical solution, a high wet etching rate can be achieved, and an underlayer film having excellent lithography properties can be formed. It is possible to provide a composition for forming a containing resist underlayer film. Further, according to the present invention, it is possible to provide a composition for forming a silicon-containing resist underlayer film that can be suitably used in a lithography process that requires further miniaturization.
- composition for forming a silicon-containing resist underlayer of the present invention comprises at least polysiloxane as component [A], a sulfonic acid compound as component [B], and an acid having a pKa of ⁇ 15.0 to 1.2. 1 and a solvent as component [C], and if necessary, other components.
- the present inventors added at least one compound selected from a sulfonic acid compound as the component [B] and an acid having a pKa of ⁇ 15.0 to 1.2 in a composition for forming a silicon-containing resist underlayer containing polysiloxane.
- a species for example, at least one selected from sulfuric acid and a sulfonic acid compound
- it can be removed by a wet etching method using a chemical solution, a high wet etching rate can be achieved, and lithography properties are also improved.
- a species for example, at least one selected from sulfuric acid and a sulfonic acid compound
- the present inventors have found that even when using a sulfonic acid compound and an acid with a pKa of -15.0 to 1.2 (for example, sulfuric acid or a sulfonic acid compound), it can be removed by wet etching using a chemical solution. In addition, it was found that a high wet etching rate can be realized and a resist underlayer film having excellent lithography properties can be formed.
- a sulfonic acid compound and an acid with a pKa of -15.0 to 1.2 for example, sulfuric acid or a sulfonic acid compound
- Polysiloxane as the [A] component is not particularly limited as long as it is a polymer having a siloxane bond.
- the polysiloxane may include a modified polysiloxane in which a portion of the silanol groups are modified, such as a modified polysiloxane in which a portion of the silanol groups are alcohol-modified or acetal-protected.
- the polysiloxane may also include, for example, a hydrolytic condensate of a hydrolyzable silane, and a modified polysiloxane in which at least part of the silanol groups of the hydrolytic condensate are alcohol-modified or acetal-protected.
- the hydrolyzable silane associated with the hydrolytic condensate can contain one or more hydrolyzable silanes.
- the polysiloxane may have any structure having a cage, ladder, linear or branched main chain. Furthermore, commercially available polysiloxane can be used as polysiloxane.
- the "hydrolytic condensate" of the hydrolyzable silane that is, the product of hydrolytic condensation, includes not only the polyorganosiloxane polymer, which is a condensate in which the condensation has been completely completed, but also Also included are polyorganosiloxane polymers that are incomplete partial hydrolytic condensates.
- Such a partially hydrolyzed condensate is also a polymer obtained by hydrolysis and condensation of a hydrolyzable silane, similar to a condensate in which the condensation is completely completed, but stops at partial hydrolysis and condenses. There are no Si--OH groups remaining.
- the silicon-containing resist underlayer film-forming composition contains uncondensed hydrolysates (complete hydrolysates, partial hydrolysates) and monomers (hydrolyzable silane).
- hydrolyzable silane may be simply referred to as "silane compound”.
- polysiloxane examples include hydrolytic condensates of hydrolyzable silanes containing at least one hydrolyzable silane represented by the following formula (1).
- R 1 is a group bonded to a silicon atom and independently of each other, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted aralkyl optionally substituted halogenated alkyl group, optionally substituted halogenated aryl group, optionally substituted halogenated aralkyl group, optionally substituted alkoxyalkyl group, optionally substituted an alkoxyaryl group, an optionally substituted alkoxyaralkyl group, or an optionally substituted alkenyl group, or an organic group having an epoxy group, an organic group having an acryloyl group, or an organic group having a methacryloyl group; It represents an organic group having a mercapto group, an organic group having an amino group, an organic group having an alkoxy group, an organic group having a sulfonyl group, an organic group having a cyano group, or a combination of two or more thereof.
- R 2 is a group
- the alkyl group may be linear, branched, or cyclic, and the number of carbon atoms thereof is not particularly limited, but is preferably 40 or less, more preferably 30 or less, and still more preferably 20 or less. , more preferably 10 or less.
- alkyl group specific examples of linear or branched alkyl groups include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group, n-pentyl group, 1-methyl-n-butyl group, 2-methyl-n-butyl group, 3-methyl-n-butyl group, 1,1-dimethyl-n-propyl group, 1,2-dimethyl-n-propyl group, 2,2-dimethyl-n-propyl group, 1-ethyl-n-propyl group, n-hexyl group, 1-methyl-n-pentyl group, 2-methyl-n -pentyl group, 3-methyl-n-pentyl group, 4-methyl-n-pentyl group, 1,1-dimethyl-n-butyl group, 1,2-dimethyl-n-butyl group, 1,3-
- cyclic alkyl groups include cyclopropyl, cyclobutyl, 1-methyl-cyclopropyl, 2-methyl-cyclopropyl, cyclopentyl, 1-methyl-cyclobutyl, 2-methyl-cyclobutyl, 3 -methyl-cyclobutyl, 1,2-dimethyl-cyclopropyl, 2,3-dimethyl-cyclopropyl, 1-ethyl-cyclopropyl, 2-ethyl-cyclopropyl, cyclohexyl, 1-methyl-cyclopentyl group, 2-methyl-cyclopentyl group, 3-methyl-cyclopentyl group, 1-ethyl-cyclobutyl group, 2-ethyl-cyclobutyl group, 3-ethyl-cyclobutyl group, 1,2-dimethyl-cyclobutyl group, 1,3- dimethyl-cyclobutyl group, 2,2-dimethyl-cyclobutyl group, 2,3-dimethyl-cyclobutyl group
- the aryl group includes a phenyl group, a monovalent group derived by removing one hydrogen atom from a condensed ring aromatic hydrocarbon compound, and 1 derived by removing one hydrogen atom from a ring-linked aromatic hydrocarbon compound.
- the number of carbon atoms is not particularly limited, but is preferably 40 or less, more preferably 30 or less, and still more preferably 20 or less.
- the aryl group includes an aryl group having 6 to 20 carbon atoms, examples of which include a phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1- phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 5-naphthacenyl group, 2-chrysenyl group, 1-pyrenyl group, 2- pyrenyl group, pentacenyl group, benzopyrenyl group, triphenylenyl group; biphenyl-2-yl group (o-biphenylyl group), biphenyl-3-yl group (m-biphenylyl group), biphenyl-4-yl group (p-biphenylyl group;
- An aralkyl group is an alkyl group substituted with an aryl group, and specific examples of such an aryl group and an alkyl group are the same as those described above.
- the number of carbon atoms in the aralkyl group is not particularly limited, it is preferably 40 or less, more preferably 30 or less, and still more preferably 20 or less.
- aralkyl groups include phenylmethyl group (benzyl group), 2-phenylethylene group, 3-phenyl-n-propyl group, 4-phenyl-n-butyl group, 5-phenyl-n-pentyl group, 6 -phenyl-n-hexyl group, 7-phenyl-n-heptyl group, 8-phenyl-n-octyl group, 9-phenyl-n-nonyl group, 10-phenyl-n-decyl group, etc., and these is not limited to
- Halogenated alkyl groups, halogenated aryl groups, and halogenated aralkyl groups are alkyl groups, aryl groups, and aralkyl groups, respectively, substituted with one or more halogen atoms, and such alkyl groups, aryl groups, and aralkyl Specific examples of the groups are the same as those mentioned above.
- Halogen atoms include fluorine, chlorine, bromine, and iodine atoms.
- halogenated alkyl groups include monofluoromethyl group, difluoromethyl group, trifluoromethyl group, bromodifluoromethyl group, 2-chloroethyl group, 2-bromoethyl group, 1,1-difluoroethyl group, 2,2 ,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group, 2-chloro-1,1,2-trifluoroethyl group, pentafluoroethyl group, 3-bromopropyl group, 2,2 , 3,3-tetrafluoropropyl group, 1,1,2,3,3,3-hexafluoropropyl group, 1,1,1,3,3,3-hexafluoropropan-2-yl
- halogenated aryl groups include 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group and 2,5-difluorophenyl group, 2,6-difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 2,3,4-trifluorophenyl group, 2,3,5-trifluorophenyl group, 2, 3,6-trifluorophenyl group, 2,4,5-trifluorophenyl group, 2,4,6-trifluorophenyl group, 3,4,5-trifluorophenyl group, 2,3,4,5- tetrafluorophenyl group, 2,
- halogenated aralkyl group is not particularly limited, it is preferably 40 or less, more preferably 30 or less, and still more preferably 20 or less.
- Specific examples of halogenated aralkyl groups include 2-fluorobenzyl, 3-fluorobenzyl, 4-fluorobenzyl, 2,3-difluorobenzyl, 2,4-difluorobenzyl and 2,5-difluorobenzyl.
- fluorine atom (fluoro group) in these groups is arbitrarily substituted with a chlorine atom (chloro group), a bromine atom (bromo group), or an iodine atom (iodo group), but is not limited thereto.
- Alkoxyalkyl, alkoxyaryl, and alkoxyaralkyl groups are alkyl, aryl, and aralkyl groups, respectively, substituted with one or more alkoxy groups, and specific examples of such alkyl, aryl, and aralkyl groups are Examples are the same as those mentioned above.
- alkoxy groups as substituents include alkoxy groups having at least one of linear, branched and cyclic alkyl moieties having 1 to 20 carbon atoms.
- linear or branched alkoxy groups include methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy and t-butoxy groups.
- n-pentyloxy group 1-methyl-n-butoxy group, 2-methyl-n-butoxy group, 3-methyl-n-butoxy group, 1,1-dimethyl-n-propoxy group, 1,2-dimethyl- n-propoxy group, 2,2-dimethyl-n-propoxy group, 1-ethyl-n-propoxy group, n-hexyloxy group, 1-methyl-n-pentyloxy group, 2-methyl-n-pentyloxy group, 3- methyl-n-pentyloxy group, 4-methyl-n-pentyloxy group, 1,1-dimethyl-n-butoxy group, 1,2-dimethyl-n-butoxy group, 1,3-dimethyl-n-butoxy group, 2 , 2-dimethyl-n-butoxy group, 2,3-dimethyl-n-butoxy group, 3,3-dimethyl-n-butoxy group, 1-ethyl-n-butoxy group, 2-ethyl-n-butoxy group, 1,1,2-trimethyl
- cyclic alkoxy groups include cyclopropoxy, cyclobutoxy, 1-methyl-cyclopropoxy, 2-methyl-cyclopropoxy, cyclopentyloxy, 1-methyl-cyclobutoxy, 2-methyl- cyclobutoxy, 3-methyl-cyclobutoxy, 1,2-dimethyl-cyclopropoxy, 2,3-dimethyl-cyclopropoxy, 1-ethyl-cyclopropoxy, 2-ethyl-cyclopropoxy, cyclohexyloxy group, 1-methyl-cyclopentyloxy group, 2-methyl-cyclopentyloxy group, 3-methyl-cyclopentyloxy group, 1-ethyl-cyclobutoxy group, 2-ethyl-cyclobutoxy group, 3-ethyl-cyclo butoxy group, 1,2-dimethyl-cyclobutoxy group, 1,3-dimethyl-cyclobutoxy group, 2,2-dimethyl-cyclobutoxy group, 2,3-dimethyl-cyclobutoxy group, 2,4-dimethyl-cyclobut
- alkoxyalkyl groups include lower (about 5 or less carbon atoms) alkyloxy lower (about 5 or less carbon atoms) groups such as methoxymethyl group, ethoxymethyl group, 1-ethoxyethyl group, 2-ethoxyethyl group and ethoxymethyl group. degree) alkyl groups and the like, but are not limited to these.
- alkoxyaryl groups include 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-(1-ethoxy)phenyl, 3-(1-ethoxy)phenyl, 4-( 1-ethoxy)phenyl group, 2-(2-ethoxy)phenyl group, 3-(2-ethoxy)phenyl group, 4-(2-ethoxy)phenyl group, 2-methoxynaphthalen-1-yl group, 3-methoxy naphthalene-1-yl group, 4-methoxynaphthalene-1-yl group, 5-methoxynaphthalene-1-yl group, 6-methoxynaphthalene-1-yl group, 7-methoxynaphthalene-1-yl group and the like. but not limited to these.
- Specific examples of the alkoxyaralkyl group include, but are not limited to, 3-(methoxyphenyl)benzyl group, 4-(methoxyphenyl)benzyl group and the
- the alkenyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 40 or less, more preferably 30 or less, still more preferably 20 or less, and further preferably 20 or less. It is preferably 10 or less.
- alkenyl groups include ethenyl (vinyl), 1-propenyl, 2-propenyl, 1-methyl-1-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2 -methyl-1-propenyl group, 2-methyl-2-propenyl group, 1-ethylethenyl group, 1-methyl-1-propenyl group, 1-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-n-propylethenyl group, 1-methyl-1-butenyl group, 1-methyl-2-butenyl group, 1-methyl-3-butenyl group, 2-ethyl- 2-propenyl group, 2-methyl-1-butenyl group, 2-methyl-2-butenyl group, 2-methyl-3-butenyl group, 3-methyl-1-butenyl group, 3-methyl-2-butenyl group, 3-methyl-3-butenyl group, 1,
- substituents for the alkyl group, aryl group, aralkyl group, halogenated alkyl group, halogenated aryl group, halogenated aralkyl group, alkoxyalkyl group, alkoxyaryl group, alkoxyaralkyl group, and alkenyl group described above include , alkyl group, aryl group, aralkyl group, halogenated alkyl group, halogenated aryl group, halogenated aralkyl group, alkoxyalkyl group, aryloxy group, alkoxyaryl group, alkoxyaralkyl group, alkenyl group, alkoxy group, aralkyloxy group etc., and specific examples thereof and suitable carbon numbers thereof are the same as those described above or below.
- the aryloxy group mentioned in the substituent group is a group to which an aryl group is bonded through an oxygen atom (--O--), and specific examples of such an aryl group are the same as those mentioned above.
- the number of carbon atoms in the aryloxy group is not particularly limited, it is preferably 40 or less, more preferably 30 or less, and still more preferably 20 or less.
- Specific examples thereof include a phenoxy group, naphthalene-2- Examples include, but are not limited to, an yloxy group and the like.
- the substituents may be combined to form a ring.
- the organic group having an epoxy group includes glycidoxymethyl group, glycidoxyethyl group, glycidoxypropyl group, glycidoxybutyl group, epoxycyclohexyl group and the like.
- the organic group having an acryloyl group includes an acryloylmethyl group, an acryloylethyl group, an acryloylpropyl group and the like.
- Examples of organic groups having a methacryloyl group include methacryloylmethyl, methacryloylethyl, and methacryloylpropyl groups.
- Organic groups having a mercapto group include mercaptoethyl, mercaptobutyl, mercaptohexyl, mercaptooctyl, and mercaptophenyl groups.
- the organic group having an amino group includes, but is not limited to, an amino group, an aminomethyl group, an aminoethyl group, an aminophenyl group, a dimethylaminoethyl group, a dimethylaminopropyl group, and the like. Further details of the organic group having an amino group will be described later.
- Examples of the organic group having an alkoxy group include, but are not limited to, methoxymethyl group and methoxyethyl group.
- organic groups having a sulfonyl group include, but are not limited to, sulfonylalkyl groups and sulfonylaryl groups.
- the organic group having a cyano group includes cyanoethyl group, cyanopropyl group, cyanophenyl group, thiocyanate group and the like.
- the organic group having an amino group includes an organic group having at least one of a primary amino group, a secondary amino group, and a tertiary amino group.
- a hydrolytic condensate obtained by hydrolyzing a hydrolyzable silane having a tertiary amino group with a strong acid to form a counter cation having a tertiary ammonium group can be preferably used.
- the organic group can contain a heteroatom such as an oxygen atom or a sulfur atom in addition to the nitrogen atom constituting the amino group.
- a preferable example of the organic group having an amino group is a group represented by the following formula (A1).
- R 101 and R 102 each independently represent a hydrogen atom or a hydrocarbon group
- L each independently represents an optionally substituted alkylene group. * represents a bond.
- Hydrocarbon groups include, but are not limited to, alkyl groups, alkenyl groups, aryl groups, and the like. Specific examples of these alkyl groups, alkenyl groups and aryl groups are the same as those described above for R 1 .
- the alkylene group may be linear or branched, and usually has 1 to 10 carbon atoms, preferably 1 to 5 carbon atoms.
- Examples thereof include linear alkylene groups such as methylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, nonamethylene and decamethylene.
- the organic group having an amino group includes, but is not limited to, an amino group, an aminomethyl group, an aminoethyl group, an aminophenyl group, a dimethylaminoethyl group, a dimethylaminopropyl group, and the like.
- R 2 examples include the alkoxy groups exemplified for R 1 .
- examples of the halogen atom for R 2 include the halogen atoms exemplified for R 1 .
- the aralkyloxy group is a monovalent group derived by removing a hydrogen atom from the hydroxy group of aralkyl alcohol, and specific examples of the aralkyl group in the aralkyloxy group are the same as those described above.
- the number of carbon atoms in the aralkyloxy group is not particularly limited, it can be, for example, 40 or less, preferably 30 or less, more preferably 20 or less.
- Specific examples of aralkyloxy groups include phenylmethyloxy group (benzyloxy group), 2-phenylethyleneoxy group, 3-phenyl-n-propyloxy group, 4-phenyl-n-butyloxy group and 5-phenyl-n.
- -pentyloxy group 6-phenyl-n-hexyloxy group, 7-phenyl-n-heptyloxy group, 8-phenyl-n-octyloxy group, 9-phenyl-n-nonyloxy group, 10-phenyl-n- Examples include, but are not limited to, a decyloxy group and the like.
- the acyloxy group is a monovalent group derived by removing a hydrogen atom from the carboxyl group (—COOH) of a carboxylic acid compound, typically from the carboxyl group of an alkylcarboxylic acid, an arylcarboxylic acid or an aralkylcarboxylic acid.
- Examples include, but are not limited to, alkylcarbonyloxy groups, arylcarbonyloxy groups, or aralkylcarbonyloxy groups derived by removing a hydrogen atom.
- Specific examples of the alkyl group, aryl group and aralkyl group in such alkylcarboxylic acid, arylcarboxylic acid and aralkylcarboxylic acid are the same as those mentioned above.
- acyloxy groups include acyloxy groups having 2 to 20 carbon atoms, such as methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, i-propylcarbonyloxy, n-butylcarbonyloxy, group, i-butylcarbonyloxy group, s-butylcarbonyloxy group, t-butylcarbonyloxy group, n-pentylcarbonyloxy group, 1-methyl-n-butylcarbonyloxy group, 2-methyl-n-butylcarbonyloxy group, 3-methyl-n-butylcarbonyloxy group, 1,1-dimethyl-n-propylcarbonyloxy group, 1,2-dimethyl-n-propylcarbonyloxy group, 2,2-dimethyl-n-propylcarbonyloxy group group, 1-ethyl-n-propylcarbonyloxy group, n-hexylcarbonyloxy group, 1-methyl-n-n
- hydrolyzable silane represented by Formula (1) includes tetramethoxysilane, tetrachlorosilane, tetraacetoxysilane, tetraethoxysilane, tetra-n-propoxysilane, tetra-i-propoxysilane, tetra-n -butoxysilane, methyltrimethoxysilane, methyltrichlorosilane, methyltriacetoxysilane, methyltriethoxysilane, methyltripropoxysilane, methyltributoxysilane, methyltriamyloxysilane, methyltriphenoxysilane, methyltribenzyloxysilane, methyltriphenethyloxysilane, glycidoxymethyltrimethoxysilane, glycidoxymethyltriethoxysilane, ⁇ -glycid
- each T independently represents an alkoxy group, an acyloxy group, or a halogen group, for example, preferably a methoxy group or an ethoxy group.
- hydrolyzed silane represented by the following formula (2) Hydrolytic condensates of hydrolyzable silanes, including hydrolysable silanes, may be mentioned.
- R 3 is a group bonded to a silicon atom and independently of each other, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted aralkyl optionally substituted halogenated alkyl group, optionally substituted halogenated aryl group, optionally substituted halogenated aralkyl group, optionally substituted alkoxyalkyl group, optionally substituted an alkoxyaryl group, an optionally substituted alkoxyaralkyl group, or an optionally substituted alkenyl group, or an organic group having an epoxy group, an organic group having an acryloyl group, or an organic group having a methacryloyl group; It represents an organic group having a mercapto group, an organic group having an amino group, an organic group having an alkoxy group, an organic group having a sulfonyl group, an organic group having a cyano group, or a combination of two or more thereof.
- R 4 is a group or atom bonded to a silicon atom and independently represents an alkoxy group, an aralkyloxy group, an acyloxy group, or a halogen atom.
- R 5 is a group bonded to a silicon atom and independently represents an alkylene group or an arylene group. b represents 0 or 1, c represents 0 or 1;
- each group in R 3 and preferred carbon numbers thereof include the groups and carbon numbers described above for R 1 .
- Specific examples of each group and atom in R 4 and their preferred carbon numbers include the groups and atoms and carbon numbers described above for R 2 .
- Specific examples of the alkylene group for R 5 include linear groups such as methylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, nonamethylene and decamethylene groups.
- alkylene group 1-methyltrimethylene group, 2-methyltrimethylene group, 1,1-dimethylethylene group, 1-methyltetramethylene group, 2-methyltetramethylene group, 1,1-dimethyltrimethylene group, 1, 2-dimethyltrimethylene group, 2,2-dimethyltrimethylene group, alkylene group such as branched alkylene group such as 1-ethyltrimethylene group, methanetriyl group, ethane-1,1,2-triyl group, ethane- 1,2,2-triyl group, ethane-2,2,2-triyl group, propane-1,1,1-triyl group, propane-1,1,2-triyl group, propane-1,2,3- triyl group, propane-1,2,2-triyl group, propane-1,1,3-triyl group, butane-1,1,1-triyl group, butane-1,1,2-triyl group, butane-1 , 1,3-triyl group, butane-1,2,3-triyl group, but
- arylene group for R 5 examples include 1,2-phenylene group, 1,3-phenylene group, 1,4-phenylene group; 1,5-naphthalenediyl group, 1,8-naphthalenediyl group, 2, 6-naphthalenediyl group, 2,7-naphthalenediyl group, 1,2-anthracenediyl group, 1,3-anthracenediyl group, 1,4-anthracenediyl group, 1,5-anthracenediyl group, 1,6- anthracenediyl group, 1,7-anthracenediyl group, 1,8-anthracenediyl group, 2,3-anthracenediyl group, 2,6-anthracenediyl group, 2,7-anthracenediyl group, 2,9-anthracenediyl A group derived by removing two hydrogen atoms on the aromatic ring of a condensed ring aromatic hydrocarbon compound such as a 2,10-an
- hydrolyzable silanes represented by formula (2) include methylenebistrimethoxysilane, methylenebistrichlorosilane, methylenebistriacetoxysilane, ethylenebistriethoxysilane, ethylenebistrichlorosilane, ethylenebistriacetoxysilane, and propylenebistriethoxysilane.
- hydrolyzable silane represented by the formula (1) and/or a hydrolyzable silane represented by the formula (2), as well as other hydrolyzable silanes listed below Hydrolytic condensates of decomposable silanes may be mentioned.
- Other hydrolyzable silanes include silane compounds having an onium group in the molecule, silane compounds having a sulfone group, silane compounds having a sulfonamide group, and silane compounds having a cyclic urea skeleton in the molecule. is not limited to
- silane compound having an onium group in the molecule hydrolyzable organosilane
- a silane compound having an onium group in its molecule is expected to effectively and efficiently promote the cross-linking reaction of hydrolyzable silane.
- a preferred example of a silane compound having an onium group in its molecule is represented by formula (3).
- R 11 is a group bonded to a silicon atom and represents an onium group or an organic group having the same.
- R 12 is a group that binds to a silicon atom and is independently of each other an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted aralkyl group, a substituted optionally substituted halogenated alkyl group, optionally substituted halogenated aryl group, optionally substituted halogenated aralkyl group, optionally substituted alkoxyalkyl group, optionally substituted alkoxyaryl group, substituted represents an optionally substituted alkoxyaralkyl group or an optionally substituted alkenyl group, or an organic group having an epoxy group, an organic group having an acryloyl group, an organic group having a methacryloyl group, or an organic group having a mercapto group , an amino group-containing organic group, or a cyano group-containing organic group, or a combination of
- R 13 is a silicon-bonded group or atom and independently represents an alkoxy group, an aralkyloxy group, an acyloxy group, or a halogen atom.
- f represents 1 or 2
- g represents 0 or 1
- the number of carbon atoms the number of carbon atoms mentioned above for R 1 can be mentioned for R 12
- the number of carbon atoms mentioned above for R 2 can be mentioned for R 13 .
- the onium group include a cyclic ammonium group and a chain ammonium group, preferably a tertiary ammonium group or a quaternary ammonium group. That is, preferred specific examples of the onium group or an organic group having it include a cyclic ammonium group or a chain ammonium group, or an organic group having at least one of these, a tertiary ammonium group or a quaternary ammonium group Or an organic group having at least one of these is preferred.
- the onium group is a cyclic ammonium group
- the nitrogen atoms constituting the ammonium group also serve as atoms constituting the ring. In this case, the nitrogen atom and the silicon atom constituting the ring are bonded directly or via a divalent linking group, and the carbon atom and the silicon atom constituting the ring are directly or via a divalent linking group.
- the silicon-bonded group R 11 is a heteroaromatic cyclic ammonium group represented by the following formula (S1).
- a 1 , A 2 , A 3 and A 4 each independently represent a group represented by any one of the following formulas (J1) to (J3), and A 1 to A At least one of 4 is a group represented by the following formula (J2), and depending on which of A 1 to A 4 the silicon atom in formula (3) bonds to, the ring formed is aromatic It is determined whether the bond between each of A 1 to A 4 and the atoms adjacent to each of them and forming a ring together is a single bond or a double bond, so as to indicate the family property.
- * represents a bond.
- each R 10 is independently a single bond, a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, a halogenated alkyl group, a halogenated aryl group, a halogenated aralkyl group, or Representing an alkenyl group, specific examples of an alkyl group, an aryl group, an aralkyl group, a halogenated alkyl group, a halogenated aryl group, a halogenated aralkyl group and an alkenyl group and their preferred carbon numbers are the same as those described above. be done.
- * represents a bond.
- R 14 independently represents an alkyl group, an aryl group, an aralkyl group, a halogenated alkyl group, a halogenated aryl group, a halogenated aralkyl group, an alkenyl group or a hydroxy group, and R 14 is
- the two R 14 may be bonded to each other to form a ring, and the ring formed by the two R 14 may be a bridged ring structure.
- the cyclic ammonium group has an adamantane ring, a norbornene ring, a spiro ring and the like.
- alkyl groups aryl groups, aralkyl groups, halogenated alkyl groups, halogenated aryl groups, halogenated aralkyl groups and alkenyl groups and their preferred carbon numbers are the same as those mentioned above.
- n 1 is an integer of 1 to 8
- m 1 is 0 or 1
- m 2 is a positive number from 0 or 1 to the maximum number of monocyclic or polycyclic substitutable is an integer of When m 1 is 0, a (4+n 1 ) membered ring containing A 1 to A 4 is constructed.
- a 5-membered ring when n1 is 1 a 6-membered ring when n1 is 2 , a 7-membered ring when n1 is 3 , an 8-membered ring when n1 is 4 ,
- n1 is 5
- it is a 9-membered ring
- n1 is 6
- it is a 10-membered ring
- n1 is 7
- it is an 11-membered ring
- n1 is 8 it is a 12-membered ring.
- a condensed ring is formed by condensing a (4+n 1 )-membered ring containing A 1 to A 3 with a 6-membered ring containing A 4 .
- a 1 to A 4 may or may not have a hydrogen atom on a ring-constituting atom, depending on which of the formulas (J1) to (J3), but A When 1 to A 4 have a hydrogen atom on a ring-constituting atom, the hydrogen atom may be substituted with R 14 .
- ring-constituting atoms other than the ring-constituting atoms in A 1 to A 4 may be substituted with R 14 .
- m2 is selected from integers from 0 or 1 to the maximum number of monocyclic or polycyclic substitutable numbers.
- the bond of the heteroaromatic cyclic ammonium group represented by formula (S1) is present at any carbon atom or nitrogen atom present in such a monocyclic or condensed ring and is directly bonded to a silicon atom, or A linking group is combined to form an organic group having a cyclic ammonium, which is bonded to a silicon atom.
- Such linking groups include, but are not limited to, alkylene groups, arylene groups, alkenylene groups, and the like. Specific examples of the alkylene group and arylene group and their preferred carbon numbers are the same as those described above.
- An alkenylene group is a divalent group derived by removing one more hydrogen atom from an alkenyl group, and specific examples of such alkenyl groups are the same as those described above.
- the number of carbon atoms in the alkenylene group is not particularly limited, it is preferably 40 or less, more preferably 30 or less, and still more preferably 20 or less. Specific examples thereof include, but are not limited to, vinylene, 1-methylvinylene, propenylene, 1-butenylene, 2-butenylene, 1-pentenylene, 2-pentenylene groups and the like.
- silane compound (hydrolyzable organosilane) represented by formula (3) having a heteroaromatic cyclic ammonium group represented by formula (S1) include the following formulas (I-1) to (I-50 ), but not limited thereto.
- the silicon-bonded group R 11 in formula (3) can be a heteroaliphatic cyclic ammonium group represented by the following formula (S2).
- a 5 , A 6 , A 7 and A 8 each independently represent a group represented by any one of the following formulas (J4) to (J6), and A 5 to A At least one of 8 is a group represented by the following formula (J5).
- Each of A 5 to A 8 and each adjacent It is determined whether the bond between the atoms forming the ring together is a single bond or a double bond. * represents a bond.
- each R 10 is independently a single bond, a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, a halogenated alkyl group, a halogenated aryl group, a halogenated aralkyl group, or Representing an alkenyl group, specific examples of an alkyl group, an aryl group, an aralkyl group, a halogenated alkyl group, a halogenated aryl group, a halogenated aralkyl group and an alkenyl group, and their preferred carbon numbers are the same as those described above. are mentioned.
- * represents a bond.
- R 15 independently represents an alkyl group, an aryl group, an aralkyl group, a halogenated alkyl group, a halogenated aryl group, a halogenated aralkyl group, an alkenyl group or a hydroxy group, and R 15 is When two or more R 15 are present, the two R 15 may be bonded to each other to form a ring, and the ring formed by the two R 15 may be a bridged ring structure. , the cyclic ammonium group has an adamantane ring, a norbornene ring, a spiro ring and the like.
- alkyl group aryl group, aralkyl group, halogenated alkyl group, halogenated aryl group, halogenated aralkyl group and alkenyl group and their preferred carbon numbers are the same as those mentioned above.
- n 2 is an integer of 1 to 8
- m 3 is 0 or 1
- m 4 is a positive number from 0 or 1 to the maximum number of monocyclic or polycyclic substitutable is an integer of When m 3 is 0, a (4+n 2 ) membered ring containing A 5 to A 8 is constructed.
- n2 is 5
- n2 is 6 it is a 10-membered ring
- n2 is 7 it is an 11-membered ring
- n2 is 8 it is a 12-membered ring.
- m 3 1, a condensed ring is formed by condensing a (4+n 2 )-membered ring containing A 5 to A 7 with a 6-membered ring containing A 8 .
- a 5 to A 8 may or may not have a hydrogen atom on a ring-constituting atom, but A When 5 to A 8 have a hydrogen atom on a ring-constituting atom, the hydrogen atom may be substituted with R 15 . In addition, ring-constituting atoms other than the ring-constituting atoms in A 5 to A 8 may be substituted with R 15 . Under these circumstances, as described above, m4 is selected from integers from 0 or 1 to the maximum number of monocyclic or polycyclic substitutable numbers.
- the bond of the heteroaliphatic cyclic ammonium group represented by formula (S2) is present at any carbon atom or nitrogen atom present in such a monocyclic or condensed ring and is directly bonded to the silicon atom, or A linking group is combined to form an organic group having a cyclic ammonium, which is bonded to a silicon atom.
- Examples of such a linking group include an alkylene group, an arylene group and an alkenylene group, and specific examples of the alkylene group, arylene group and alkenylene group and their preferred carbon numbers are the same as those described above.
- silane compound (hydrolyzable organosilane) represented by the formula (3) having a heteroaliphatic cyclic ammonium group represented by the formula (S2) include the following formulas (II-1) to (II- 30), but not limited thereto.
- R 11 which is a silicon-bonded group in formula (3), can be a chain ammonium group represented by formula (S3) below.
- R 10 each independently represents a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, a halogenated alkyl group, a halogenated aryl group, a halogenated aralkyl group or an alkenyl group, an alkyl group, Specific examples of the aryl group, aralkyl group, halogenated alkyl group, halogenated aryl group, halogenated aralkyl group and alkenyl group and their preferred carbon numbers are the same as those mentioned above. * represents a bond.
- the chain ammonium group represented by formula (S3) is directly bonded to a silicon atom, or is bonded to a linking group to form an organic group having a chain ammonium group, which is bonded to a silicon atom.
- a linking group include an alkylene group, an arylene group and an alkenylene group, and specific examples of the alkylene group, arylene group and alkenylene group are the same as those described above.
- silane compound (hydrolyzable organosilane) represented by formula (3) having a chain ammonium group represented by formula (S3) include the following formulas (III-1) to (III-28). Examples include, but are not limited to, silanes represented by.
- silane compound having sulfone group or sulfonamide group hydrolyzable organosilane
- examples of the silane compound having a sulfone group and the silane compound having a sulfonamide group include, but are not limited to, compounds represented by the following formulas (B-1) to (B-36). In the formula below, Me represents a methyl group, and Et represents an ethyl group.
- Hydrolyzable organosilanes having a cyclic urea skeleton in the molecule include, for example, hydrolyzable organosilanes represented by the following formula (4-1).
- R 401 is a group bonded to a silicon atom and independently represents a group represented by formula (4-2) below.
- R 402 is a group bonded to a silicon atom, optionally substituted alkyl group, optionally substituted aryl group, optionally substituted aralkyl group, optionally substituted halogenated alkyl group , optionally substituted halogenated aryl group, optionally substituted halogenated aralkyl group, optionally substituted alkoxyalkyl group, optionally substituted alkoxyaryl group, optionally substituted alkoxy represents an aralkyl group or an optionally substituted alkenyl group, or an organic group having an epoxy group, an organic group having an acryloyl group, an organic group having a methacryloyl group, an organic group having a mercapto group, or an organic group having a cyano group group, or a combination of two or more thereof.
- R 403 is a group or atom bonded to a silicon atom and independently represents an alkoxy group, an aralkyloxy group, an acyloxy group or a halogen atom.
- x is 1 or 2
- y is 0 or 1, and satisfies x+y ⁇ 2.
- R 402 alkyl group, aryl group, aralkyl group, halogenated alkyl group, halogenated aryl group, halogenated aralkyl group, alkoxyalkyl group, alkoxyaryl group, alkoxyaralkyl group, alkenyl group, and an organic group having an epoxy group , an organic group having an acryloyl group, an organic group having a methacryloyl group, an organic group having a mercapto group, an organic group having a cyano group, and an alkoxy group, an aralkyloxy group, an acyloxy group and a halogen atom of R 403 , and these Specific examples of substituents, preferred number of carbon atoms, etc. are the same as those described above for R 1 and R 2 .
- R 404 each independently has a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, or an organic group having an epoxy group or a sulfonyl group Representing an organic group
- R 405 is independently an alkylene group, a hydroxyalkylene group, a sulfide bond (-S-), an ether bond (-O-) or an ester bond (-CO-O- or -O-CO -).
- * represents a bond.
- Specific examples of the optionally substituted alkyl group, optionally substituted alkenyl group, and epoxy group-containing organic group for R 404 and the preferred number of carbon atoms are the same as those described above for R 1 .
- the optionally substituted alkyl group for R 404 is preferably an alkyl group having a terminal hydrogen atom substituted with a vinyl group, and specific examples thereof include allyl group, 2-vinylethyl group, 3-vinylpropyl group, 4-vinylbutyl group and the like.
- the organic group having a sulfonyl group is not particularly limited as long as it contains a sulfonyl group, optionally substituted alkylsulfonyl group, optionally substituted arylsulfonyl group, optionally substituted aralkylsulfonyl group.
- optionally substituted halogenated alkylsulfonyl group optionally substituted halogenated arylsulfonyl group, optionally substituted halogenated aralkylsulfonyl group, optionally substituted alkoxyalkylsulfonyl group, substituted optionally substituted alkoxyarylsulfonyl group, optionally substituted alkoxyaralkylsulfonyl group, optionally substituted alkenylsulfonyl group, and the like.
- Specific examples and preferred number of carbon atoms are the same as those described above for R 1 .
- the alkylene group is a divalent group derived by removing one more hydrogen atom from an alkyl group, and may be linear, branched, or cyclic. Specific examples of such an alkylene group include , the same as those described above. Although the number of carbon atoms in the alkylene group is not particularly limited, it is preferably 40 or less, more preferably 30 or less, even more preferably 20 or less, still more preferably 10 or less.
- the alkylene group of R 405 may have one or more selected from a sulfide bond, an ether bond and an ester bond at the terminal or in the middle, preferably in the middle.
- the alkylene group include linear alkylene groups such as methylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, nonamethylene, and decamethylene, methylethylene group, 1-methyltrimethylene group, 2-methyltrimethylene group, 1,1-dimethylethylene group, 1-methyltetramethylene group, 2-methyltetramethylene group, 1,1-dimethyltrimethylene group, 1 , 2-dimethyltrimethylene group, 2,2-dimethyltrimethylene group, branched alkylene groups such as 1-ethyltrimethylene group, 1,2-cyclopropanediyl group, 1,2-cyclobutanediyl group, 1, Cyclic alkylenes such as 3-cyclobutylene group
- the hydroxyalkylene group is obtained by replacing at least one of the hydrogen atoms of the alkylene group described above with a hydroxy group.
- a hydroxymethylene group a 1-hydroxyethylene group, a 2-hydroxyethylene group, 2-dihydroxyethylene group, 1-hydroxytrimethylene group, 2-hydroxytrimethylene group, 3-hydroxytrimethylene group, 1-hydroxytetramethylene group, 2-hydroxytetramethylene group, 3-hydroxytetramethylene group, 4- hydroxytetramethylene group, 1,2-dihydroxytetramethylene group, 1,3-dihydroxytetramethylene group, 1,4-dihydroxytetramethylene group, 2,3-dihydroxytetramethylene group, 2,4-dihydroxytetramethylene group, Examples include, but are not limited to, 4,4-dihydroxytetramethylene group.
- X 401 independently represents any one of the groups represented by the following formulas (4-3) to (4-5), and the following formula (4-4) and the carbon atom of the ketone group in formula (4-5) is bonded to the nitrogen atom to which R 405 in formula (4-2) is bonded.
- R 406 to R 410 are each independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, or an epoxy represents an organic group having a group or a sulfonyl group.
- Specific examples of an optionally substituted alkyl group, an optionally substituted alkenyl group, an epoxy group, or an organic group having a sulfonyl group, and preferred number of carbon atoms are the same as those described above for R 1 .
- specific examples of the organic group having a sulfonyl group and preferred number of carbon atoms are the same as those described above for R 404 .
- * represents a bond.
- X 401 is preferably a group represented by formula (4-5) from the viewpoint of realizing excellent lithography properties with good reproducibility.
- At least one of R 404 and R 406 to R 410 is preferably an alkyl group having a terminal hydrogen atom substituted with a vinyl group.
- a commercially available product may be used for the hydrolyzable organosilane represented by formula (4-1), or it may be synthesized by a known method described in International Publication No. 2011/102470 or the like.
- hydrolyzable organosilane represented by the formula (4-1) include silanes represented by the following formulas (4-1-1) to (4-1-29). , but not limited to.
- Polysiloxane can be a hydrolytic condensate of a hydrolyzable silane containing a silane compound other than those exemplified above as long as it does not impair the effects of the present invention.
- modified polysiloxane in which at least part of the silanol groups have been modified can be used as [A] polysiloxane.
- a modified polysiloxane in which some of the silanol groups are alcohol-modified or an acetal-protected polysiloxane modified product can be used.
- the modified polysiloxane is a reaction product obtained by reacting at least part of the silanol groups of the condensate with the hydroxy groups of the alcohol in the hydrolytic condensate of the hydrolyzable silane described above. Examples include a dehydration reaction product of a compound and an alcohol, and a modified product obtained by protecting at least part of the silanol groups of the condensate with an acetal group.
- Monohydric alcohols can be used as alcohols such as methanol, ethanol, 2-propanol, 1-butanol, 2-butanol, isobutyl alcohol, tert-butyl alcohol, 1-pentanol, 2-pentanol, 3- Pentanol, 1-heptanol, 2-heptanol, tert-amyl alcohol, neopentyl alcohol, 2-methyl-1-propanol, 2-methyl-1-butanol, 3-methyl-1-butanol, 3-methyl-3- pentanol, cyclopentanol, 1-hexanol, 2-hexanol, 3-hexanol, 2,3-dimethyl-2-butanol, 3,3-dimethyl-1-butanol, 3,3-dimethyl-2-butanol, 2 -diethyl-1-butanol, 2-methyl-1-pentanol, 2-methyl-2-pentanol, 2-methyl-3-pentano
- 3-methoxybutanol ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether (1-methoxy-2-propanol), propylene glycol monoethyl ether (1-ethoxy -2-propanol), propylene glycol monobutyl ether (1-butoxy-2-propanol) and other alkoxy group-containing alcohols can be used.
- the reaction between the silanol group of the condensate and the hydroxy group of the alcohol is carried out by contacting the polysiloxane with the alcohol and reacting at a temperature of 40 to 160° C., for example, 60° C., for 0.1 to 48 hours, for example, 24 hours.
- a modified polysiloxane with capped silanol groups is obtained.
- the alcohol of the capping agent can be used as a solvent in the composition containing polysiloxane.
- a dehydration reaction product of alcohol and polysiloxane which is a hydrolytic condensate of hydrolyzable silane, is prepared by reacting polysiloxane with alcohol in the presence of an acid as a catalyst, capping the silanol groups with alcohol, and dehydrating. It can be produced by removing the generated water out of the reaction system.
- an organic acid having an acid dissociation constant (pka) of -1 to 5, preferably 4 to 5 can be used as the acid.
- the acid can be trifluoroacetic acid, maleic acid, benzoic acid, isobutyric acid, acetic acid, etc. Among them, benzoic acid, isobutyric acid, acetic acid, etc. can be exemplified.
- an acid having a boiling point of 70 to 160° C. can be used, and examples thereof include trifluoroacetic acid, isobutyric acid, acetic acid, nitric acid and the like.
- the acid preferably has either an acid dissociation constant (pka) of 4 to 5 or a boiling point of 70 to 160°C. That is, one with weak acidity or one with strong acidity but low boiling point can be used.
- pka acid dissociation constant
- the acid it is possible to use any of the properties of the acid dissociation constant and the boiling point.
- the silanol group of the condensate can be acetal-protected using a vinyl ether, for example, a vinyl ether represented by the following formula (5). can be introduced into
- R 1a , R 2a and R 3a each represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms
- R 4a represents an alkyl group having 1 to 10 carbon atoms
- R 2a and R 4a may combine with each other to form a ring.
- Examples of the alkyl group can be exemplified above.
- R 1 ', R 2 ', and R 3 ' each represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms
- R 4 ' represents an alkyl group having 1 to 10 carbon atoms
- R 2 ' and R 4 ' may combine with each other to form a ring.
- * indicates a bond with an adjacent atom. Adjacent atoms include, for example, oxygen atoms in siloxane bonds, oxygen atoms in silanol groups, and carbon atoms derived from R 1 in formula (1). Examples of the alkyl group can be exemplified above.
- Examples of the vinyl ether represented by formula (5) include aliphatic vinyl ether compounds such as methyl vinyl ether, ethyl vinyl ether, isopropyl vinyl ether, normal butyl vinyl ether, 2-ethylhexyl vinyl ether, tert-butyl vinyl ether, and cyclohexyl vinyl ether; -dihydrofuran, 4-methyl-2,3-dihydrofuran, and 3,4-dihydro-2H-pyran can be used.
- ethyl vinyl ether propyl vinyl ether, butyl vinyl ether, ethylhexyl vinyl ether, cyclohexyl vinyl ether, 3,4-dihydro-2H-pyran, or 2,3-dihydrofuran can be preferably used.
- Acetal protection of silanol groups can be achieved by using polysiloxane, vinyl ether, and an aprotic solvent such as propylene glycol monomethyl ether acetate, ethyl acetate, dimethylformamide, tetrahydrofuran, or 1,4-dioxane as a solvent, pyridium paratoluenesulfonic acid. , trifluoromethanesulfonic acid, p-toluenesulfonic acid, methanesulfonic acid, hydrochloric acid, sulfuric acid and the like.
- an aprotic solvent such as propylene glycol monomethyl ether acetate, ethyl acetate, dimethylformamide, tetrahydrofuran, or 1,4-dioxane
- pyridium paratoluenesulfonic acid pyridium paratoluenesulfonic acid.
- trifluoromethanesulfonic acid
- the capping of the silanol group with an alcohol and the acetal protection may be performed simultaneously with the hydrolysis and condensation of the hydrolyzable silane, which will be described later.
- [A] polysiloxane is a hydrolyzable silane represented by formula (1), optionally a hydrolyzable silane represented by formula (2), and other hydrolyzable at least one of hydrolytic condensates of hydrolyzable silanes and modified products thereof, including silanes.
- [A] polysiloxane contains a dehydration reaction product of a hydrolytic condensate and an alcohol.
- the hydrolytic condensate (which may also include modified products) of hydrolyzable silane can have a weight average molecular weight of, for example, 500 to 1,000,000.
- the weight average molecular weight is preferably 500,000 or less, more preferably 250,000 or less, and still more preferably 100,000 or less. It is preferably 700 or more, more preferably 1,000 or more, from the viewpoint of compatibility between storage stability and coatability.
- a weight average molecular weight is a molecular weight obtained by polystyrene conversion by GPC analysis.
- GPC analysis for example, GPC apparatus (trade name HLC-8220GPC, manufactured by Tosoh Corporation), GPC column (trade name Shodex (registered trademark) KF803L, KF802, KF801, manufactured by Showa Denko Co., Ltd.), the column temperature is 40 ° C., Tetrahydrofuran can be used as an eluent (elution solvent), the flow rate (flow rate) can be set to 1.0 mL/min, and polystyrene (Shodex (registered trademark) manufactured by Showa Denko KK) can be used as a standard sample.
- GPC apparatus trade name HLC-8220GPC, manufactured by Tosoh Corporation
- GPC column trade name Shodex (registered trademark) KF803L, KF802, KF801, manufactured by Showa Denko Co., Ltd.
- Tetrahydrofuran can be used as an eluent (elution solvent)
- the flow rate (flow rate) can be
- a hydrolytic condensate of hydrolyzable silane is obtained by hydrolyzing and condensing the aforementioned silane compound (hydrolyzable silane).
- the aforementioned silane compounds (hydrolyzable silanes) contain an alkoxy group, an aralkyloxy group, an acyloxy group, or a halogen atom directly bonded to a silicon atom, i.e., an alkoxysilyl group, an aralkyloxysilyl group, an acyloxysilyl group, or a halogen atom.
- silyl groups hereinafter referred to as hydrolyzable groups).
- water is generally used in an amount of 0.1 to 100 mol, for example 0.5 to 100 mol, preferably 1 to 10 mol, per 1 mol of hydrolyzable group.
- a hydrolysis catalyst may be used for the purpose of promoting the reaction, or the hydrolysis and condensation may be performed without using a hydrolysis catalyst.
- a hydrolysis catalyst it can be used in an amount of usually 0.0001 to 10 mol, preferably 0.001 to 1 mol, per 1 mol of hydrolyzable group.
- the reaction temperature for hydrolysis and condensation is generally room temperature or higher and the reflux temperature or lower of the organic solvent that can be used for hydrolysis at normal pressure, for example, 20 to 110°C, or for example, 20 to 80°C.
- the hydrolysis may be complete hydrolysis, ie converting all hydrolyzable groups to silanol groups, or it may be partially hydrolyzed, ie leaving unreacted hydrolyzable groups.
- Hydrolysis catalysts that can be used for hydrolysis and condensation include metal chelate compounds, organic acids, inorganic acids, organic bases, and inorganic bases.
- Metal chelate compounds as hydrolysis catalysts include, for example, triethoxy mono(acetylacetonato)titanium, tri-n-propoxy mono(acetylacetonato)titanium, tri-i-propoxy mono(acetylacetonato)titanium, tri -n-butoxy mono(acetylacetonato)titanium, tri-sec-butoxy mono(acetylacetonato)titanium, tri-t-butoxy mono(acetylacetonato)titanium, diethoxy bis(acetylacetonato)titanium , di-n-propoxy bis (acetylacetonato) titanium, di-i-propoxy bis (acetylacetonato) titanium, di-n-butoxy bis (acetylacetonate) titanium, di-sec-butoxy bis (acetylacetonato)titanium, di-t-butoxy bis(acet
- Organic acids as hydrolysis catalysts are, for example, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, oxalic acid, maleic acid, methylmalonic acid, adipic acid, sebacine.
- Acid gallic acid, butyric acid, mellitic acid, arachidonic acid, 2-ethylhexanoic acid, oleic acid, stearic acid, linoleic acid, linoleic acid, salicylic acid, benzoic acid, p-aminobenzoic acid, p-toluenesulfonic acid, benzenesulfone Acids include, but are not limited to, monochloroacetic acid, dichloroacetic acid, trichloroacetic acid, trifluoroacetic acid, formic acid, malonic acid, sulfonic acid, phthalic acid, fumaric acid, citric acid, tartaric acid, and the like.
- inorganic acids as hydrolysis catalysts include, but are not limited to, hydrochloric acid, nitric acid, sulfuric acid, hydrofluoric acid, and phosphoric acid.
- Organic bases as hydrolysis catalysts include, for example, pyridine, pyrrole, piperazine, pyrrolidine, piperidine, picoline, trimethylamine, triethylamine, monoethanolamine, diethanolamine, dimethylmonoethanolamine, monomethyldiethanolamine, triethanolamine, diazabicyclooctane, dia Zabicyclononane, diazabicycloundecene, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, trimethylphenylammonium hydroxide, benzyltrimethylammonium hydroxide, benzyltriethylammonium hydroxide etc., but not limited to these.
- inorganic bases as hydrolysis catalysts include, but are not limited to, ammonia, sodium hydroxide, potassium hydroxide, barium hydroxide, and calcium hydroxide.
- metal chelate compounds organic acids, and inorganic acids are preferred, and these may be used singly or in combination of two or more.
- nitric acid can be preferably used as the hydrolysis catalyst in the present invention.
- the storage stability of the reaction solution after hydrolysis and condensation can be improved, and in particular, changes in the molecular weight of the hydrolyzed condensate can be suppressed.
- the stability of hydrolytic condensates in liquid depends on the pH of the solution.
- nitric acid can also be used when obtaining a modified hydrolytic condensate, for example, when capping a silanol group with an alcohol. It is also preferable from the viewpoint that it can contribute to both reactions of alcohol capping of substances.
- An organic solvent may be used as a solvent for the hydrolysis and condensation, and specific examples include n-pentane, i-pentane, n-hexane, i-hexane, n-heptane, i-heptane, 2, Aliphatic hydrocarbon solvents such as 2,4-trimethylpentane, n-octane, i-octane, cyclohexane, methylcyclohexane; benzene, toluene, xylene, ethylbenzene, trimethylbenzene, methylethylbenzene, n-propylbenzene, i-propyl Aromatic hydrocarbon solvents such as benzene, diethylbenzene, i-butylbenzene, triethylbenzene, di-i-propylbenzene, n-amylnaphthalene; methanol, ethanol, n-
- reaction solution is diluted or concentrated, neutralized, and treated with an ion-exchange resin to hydrolyze the acids, bases, etc. used in the hydrolysis and condensation.
- Catalyst can be removed.
- by-products such as alcohol and water, and the used hydrolysis catalyst can be removed from the reaction solution by vacuum distillation or the like.
- the hydrolytic condensate (hereinafter also referred to as polysiloxane) thus obtained is obtained in the form of a polysiloxane varnish dissolved in an organic solvent, and this is directly used as a composition for forming a silicon-containing resist underlayer film.
- the reaction solution can be used as it is (or diluted) for the preparation of the composition for forming a silicon-containing resist underlayer film. It may remain in the reaction solution as long as it does not impair the effects of the invention. For example, about 100 ppm to 5,000 ppm of nitric acid used as a hydrolysis catalyst or alcohol capping of silanol groups may remain in the polymer varnish solution.
- the obtained polysiloxane varnish may be subjected to solvent replacement or may be diluted with a solvent as appropriate.
- the resulting polysiloxane varnish may have a film-forming component concentration of 100% by distilling off the organic solvent if the storage stability is not poor.
- the film-forming component refers to a component excluding the solvent component from all components of the composition.
- the organic solvent used for solvent replacement, dilution, etc. of the polysiloxane varnish may be the same as or different from the organic solvent used for the hydrolysis and condensation reaction of the hydrolyzable silane.
- the diluting solvent is not particularly limited, and one or two or more can be arbitrarily selected and used.
- Component [B] is at least one selected from sulfonic acid compounds and acids having a pKa (acid dissociation constant) of -15.0 to 1.2.
- the [B] component is, for example, at least one selected from sulfuric acid (H 2 SO 4 ) and sulfonic acid compounds.
- a sulfonic acid compound in the present invention is a compound having a sulfo group (--SO 3 H).
- the acid dissociation constant (pKa) is an index that quantitatively expresses the strength of an acid (the ease with which hydrogen ions dissociate).
- the acid dissociation constant (pKa) can be determined, for example, by neutralization titration, absorption photometry, capillary electrophoresis, and the like.
- the sulfonic acid compound preferably has a hydroxy group from the viewpoint of sufficiently obtaining the effects of the present invention.
- the number is not particularly limited.
- the number ratio (S:H) of the sulfo group (S) and the hydroxy group (H) in the sulfonic acid compound is not particularly limited, but is, for example, 3:1 to 1: 3.
- the sulfonic acid compound preferably has a halogen atom, more preferably a halogenated hydrocarbon group, from the viewpoint of sufficiently obtaining the effects of the present invention.
- the number of carbon atoms in the halogenated hydrocarbon group is, for example, 1-10.
- the sulfonic acid compound may be a low-molecular-weight compound or a high-molecular-weight compound.
- the sulfonic acid compound may be liquid or solid at 25° C. and 1.01 ⁇ 10 5 Pa.
- the molecular weight of the sulfonic acid compound is not particularly limited, but it is, for example, 96 to 1,000 from the viewpoint of suppressing volatilization during heating and the viewpoint of avoiding precipitation and non-uniformity in the composition. .
- the ratio of sulfo groups (--SO 3 H; molecular weight 81) in the sulfonic acid compound is not particularly limited, but is preferably 50 to 500 in terms of mass of the sulfonic acid compound per 1 mol of sulfo groups.
- sulfonic acid compound examples include, but are not limited to, the compounds represented below.
- These compounds are polysiloxanes.
- R represents an alkyl group, an aralkyl group, or an acyl group.
- X is hydroxide (OH), halogen (F, Cl, Br, I), nitric acid (NO 3 ), carboxylic acid (R'-COO), sulfonic acid (R'-SO 3 ), imide (R' —SO 2 NSO 2 —R′′), or amide (R′—SO 2 N—R′′)
- R′ and R′′ are each independently an optionally substituted alkyl group, substituted optionally substituted aryl group, optionally substituted aralkyl group, optionally substituted halogenated alkyl group, optionally substituted halogenated aryl group, optionally substituted halogenated aralkyl group, represents an optionally substituted alkoxyalkyl group, an optionally substituted alkoxyaryl group, or an optionally substituted alkoxyaralkyl group Specific examples of these groups and their preferred carbon numbers are as follows: The groups and carbon numbers
- Acids with a pKa of -15.0 to 1.2 are not particularly limited. Some sulfonic acid compounds have a pKa of -15.0 to 1.2. Such a sulfonic acid compound with a pKa of -15.0 to 1.2 is both a sulfonic acid compound and an acid with a pKa of -15.0 to 1.2.
- acids with a pKa of -15.0 to 1.2 include perhalogen acids with a pKa of -15.0 to 1.2, phosphoric acids with a pKa of -15.0 to 1.2, Examples thereof include boric acids having a pKa of -15.0 to 1.2 and sulfonimides having a pKa of -15.0 to 1.2.
- perhalic acid having a pKa of -15.0 to 1.2 include perchloric acid and periodic acid.
- Phosphoric acids with a pKa of -15.0 to 1.2 include, for example, hexafluorophosphoric acid.
- boric acids having a pKa of -15.0 to 1.2 include tetrafluoroboric acid.
- Examples of sulfonimides having a pKa of -15.0 to 1.2 include bistrifluoromethanesulfonimide acid.
- the content of component [B] in the composition for forming a silicon-containing resist underlayer film is preferably 0.05 to 20 parts per 100 parts by mass of [A] polysiloxane, from the viewpoint of obtaining the effect of the present invention more sufficiently. Parts by weight, more preferably 0.1 to 15 parts by weight, and even more preferably 0.5 to 10 parts by weight.
- the solvent as the [C] component is particularly a solvent that can dissolve and mix the [A] component, the [B] component, and, if necessary, other components contained in the silicon-containing resist underlayer film-forming composition. Can be used without restrictions.
- the solvent is preferably an alcohol solvent, more preferably an alcohol solvent such as alkylene glycol monoalkyl ether, and still more preferably propylene glycol monoalkyl ether. Since these solvents are also capping agents for the silanol groups of polysiloxane, the composition for forming a silicon-containing resist underlayer film can be extracted from the solution obtained by preparing [A] polysiloxane without the need for solvent substitution. can be prepared.
- Alkylene glycol monoalkyl ethers include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether (1-methoxy-2-propanol), propylene glycol monoethyl ether ( 1-ethoxy-2-propanol), methyl isobutyl carbinol, propylene glycol monobutyl ether and the like.
- [C] solvents include methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol propylene glycol monomethyl ether acetate (1-methoxy-2-propanol monoacetate), propylene glycol monoethyl ether acetate, and propylene glycol monopropyl.
- ether acetate propylene glycol monobutyl ether acetate, toluene, xylene, methyl ethyl ketone, cyclopentanone, cyclohexanone, ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, ethyl ethoxyacetate, ethyl hydroxyacetate, 2-hydroxy -methyl 3-methylbutanoate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, methyl 3-ethoxypropionate, methyl pyruvate, ethyl pyruvate, ethylene glycol monomethyl ether acetate, ethylene Glycol monoethyl ether acetate, ethylene glycol monopropyl ether acetate, ethylene glycol monobutyl ether acetate, diethylene glycol dimethyl ether, diethylene glycol diethyl
- the composition for forming a silicon-containing resist underlayer film of the present invention may contain water as a solvent.
- water When water is contained as a solvent, its content is, for example, 30% by mass or less, preferably 20% by mass or less, and even more preferably 15% by mass or less, relative to the total mass of the solvent contained in the composition. be able to.
- the composition for forming a silicon-containing resist underlayer film may be a composition containing no curing catalyst, but preferably contains a curing catalyst (component [D]).
- component [D] curing catalyst
- Ammonium salts, phosphines, phosphonium salts, sulfonium salts, etc. can be used as curing catalysts.
- the following salts described as examples of curing catalysts may be added in the form of salts, or those that form salts in the composition (when added, they are added as separate compounds and form salts in the system. thing).
- formula (D-1) (In the formula, m a represents an integer of 2 to 11, n a represents an integer of 2 to 3, R 21 represents an alkyl group, an aryl group, or an aralkyl group, and Y - represents an anion.)
- R 22 , R 23 , R 24 and R 25 each independently represent an alkyl group, an aryl group or an aralkyl group; Y — represents an anion; and R 22 , R 23 , R 24 and R 25 are each bound to a nitrogen atom.
- Formula (D-3) (wherein R 26 and R 27 independently represent an alkyl group, an aryl group, or an aralkyl group, and Y- represents an anion), a quaternary ammonium salt having a structure represented by
- Formula (D-5) (Wherein, R 29 and R 30 independently represent an alkyl group, an aryl group, or an aralkyl group, and Y — represents an anion), a quaternary ammonium salt having a structure represented by
- the formula (D-7) (wherein R 31 , R 32 , R 33 and R 34 each independently represent an alkyl group, an aryl group or an aralkyl group, Y- represents an anion, and R 31 , R 32 , Each of R 33 and R 34 is bound to a phosphorus atom.).
- the formula (D-8) (Wherein, R 35 , R 36 and R 37 independently represent an alkyl group, an aryl group or an aralkyl group; Y — represents an anion; and R 35 , R 36 and R 37 are each bonded to a sulfur atom.) can be mentioned.
- the compound of formula (D-1) is a quaternary ammonium salt derived from an amine, where m a represents an integer of 2-11 and n a represents an integer of 2-3.
- R 21 of this quaternary ammonium salt represents, for example, an alkyl group having 1 to 18 carbon atoms, preferably 2 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, or an aralkyl group having 7 to 18 carbon atoms, such as Linear alkyl groups such as ethyl group, propyl group and butyl group, benzyl group, cyclohexyl group, cyclohexylmethyl group, dicyclopentadienyl group and the like can be mentioned.
- the anion (Y ⁇ ) includes halide ions such as chloride ion (Cl ⁇ ), bromide ion (Br ⁇ ), iodine ion (I ⁇ ), carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ), alcoholate (—O ⁇ ) and other acid groups.
- halide ions such as chloride ion (Cl ⁇ ), bromide ion (Br ⁇ ), iodine ion (I ⁇ ), carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ), alcoholate (—O ⁇ ) and other acid groups.
- the compound of formula (D-2) is a quaternary ammonium salt represented by R 22 R 23 R 24 R 25 N + Y - .
- R 22 , R 23 , R 24 and R 25 of this quaternary ammonium salt are, for example, an alkyl group having 1 to 18 carbon atoms such as an ethyl group, a propyl group, a butyl group, a cyclohexyl group and a cyclohexylmethyl group; or an aralkyl group having 7 to 18 carbon atoms such as a benzyl group.
- Anions (Y ⁇ ) include halide ions such as chloride ion (Cl ⁇ ), bromide ion (Br ⁇ ), iodine ion (I ⁇ ), carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ). , alcoholate (—O ⁇ ) and other acid groups.
- the quaternary ammonium salts are commercially available, for example tetramethylammonium acetate, tetrabutylammonium acetate, triethylbenzylammonium chloride, triethylbenzylammonium bromide, trioctylmethylammonium chloride, tributylbenzyl chloride. Ammonium, trimethylbenzylammonium chloride and the like are exemplified.
- the compound of formula (D-3) is a quaternary ammonium salt derived from 1-substituted imidazole, R 26 and R 27 have, for example, 1 to 18 carbon atoms, and R 26 and R 27 The total number of carbon atoms is preferably 7 or more.
- R 26 can be exemplified by alkyl groups such as methyl group, ethyl group and propyl group, aryl groups such as phenyl group, and aralkyl groups such as benzyl group
- R 27 can be exemplified by aralkyl groups such as benzyl group, octyl group
- An alkyl group such as an octadecyl group can be exemplified.
- Anions (Y ⁇ ) include halide ions such as chloride ion (Cl ⁇ ), bromide ion (Br ⁇ ), iodine ion (I ⁇ ), carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ). , alcoholate (—O ⁇ ) and other acid groups.
- this compound can be obtained as a commercial product, for example, imidazole compounds such as 1-methylimidazole and 1-benzylimidazole, aralkyl halides such as benzyl bromide, methyl bromide and benzene bromide, halogenated It can be produced by reacting alkyl and halogenated aryl.
- the compound of formula (D-4) is a quaternary ammonium salt derived from pyridine, and R 28 is, for example, an alkyl group having 1 to 18 carbon atoms, preferably 4 to 18 carbon atoms, or an aralkyl group having 7 to 18 carbon atoms such as a butyl group, an octyl group, a benzyl group and a lauryl group.
- Anions (Y ⁇ ) include halide ions such as chloride ion (Cl ⁇ ), bromide ion (Br ⁇ ), iodine ion (I ⁇ ), carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ).
- This compound can be obtained as a commercial product, and is produced, for example, by reacting pyridine with an alkyl halide such as lauryl chloride, benzyl chloride, benzyl bromide, methyl bromide, octyl bromide, or an aryl halide. can do.
- alkyl halide such as lauryl chloride, benzyl chloride, benzyl bromide, methyl bromide, octyl bromide, or an aryl halide.
- alkyl halide such as lauryl chloride, benzyl chloride, benzyl bromide, methyl bromide, octyl bromide, or an aryl halide.
- alkyl halide such as lauryl chloride, benzyl chloride, benzyl bromide, methyl bromide, octyl bromide, or an aryl halide.
- the compound of formula (D-5) is a quaternary ammonium salt derived from a substituted pyridine typified by picoline and the like, and R 29 is, for example, alkyl having 1 to 18 carbon atoms, preferably 4 to 18 carbon atoms. , an aryl group having 6 to 18 carbon atoms, or an aralkyl group having 7 to 18 carbon atoms, such as a methyl group, an octyl group, a lauryl group, and a benzyl group.
- R 30 is, for example, an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 carbon atoms, or an aralkyl group having 7 to 18 carbon atoms, and for example, the compound represented by formula (D-5) is picoline When it is a quaternary ammonium derived from, R 30 is a methyl group.
- Anions (Y ⁇ ) include halide ions such as chloride ion (Cl ⁇ ), bromide ion (Br ⁇ ), iodine ion (I ⁇ ), carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ). , alcoholate (—O ⁇ ) and other acid groups.
- This compound is also commercially available, and for example, by reacting a substituted pyridine such as picoline with an alkyl halide such as methyl bromide, octyl bromide, lauryl chloride, benzyl chloride, benzyl bromide, or an aryl halide.
- an alkyl halide such as methyl bromide, octyl bromide, lauryl chloride, benzyl chloride, benzyl bromide, or an aryl halide.
- alkyl halide such as methyl bromide, octyl bromide, lauryl chloride, benzyl chloride, benzyl bromide, or an aryl halide.
- the compound of formula (D-6) is a tertiary ammonium salt derived from an amine, where m a represents an integer of 2-11 and n a represents 2 or 3.
- the anion (Y ⁇ ) includes halide ions such as chloride ion (Cl ⁇ ), bromide ion (Br ⁇ ), iodine ion (I ⁇ ), carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ), alcoholate (—O ⁇ ) and other acid groups.
- This compound can be produced by reacting an amine with a weak acid such as a carboxylic acid or phenol.
- Carboxylic acids include formic acid and acetic acid.
- the anion (Y ⁇ ) is (HCOO ⁇ ), and when acetic acid is used, the anion (Y ⁇ ) is (CH 3 COO - ). Also, when phenol is used, the anion (Y ⁇ ) is (C 6 H 5 O ⁇ ).
- the compound of formula (D-7) is a quaternary phosphonium salt having a structure of R 31 R 32 R 33 R 34 P + Y- .
- R 31 , R 32 , R 33 and R 34 are, for example, an alkyl group having 1 to 18 carbon atoms such as ethyl group, propyl group, butyl group and cyclohexylmethyl, and an aryl group having 6 to 18 carbon atoms such as phenyl group.
- an aralkyl group having 7 to 18 carbon atoms such as a benzyl group
- three of the four substituents R 31 to R 34 are an unsubstituted phenyl group or a substituted phenyl group, such as phenyl and tolyl groups, and the remaining one is an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 carbon atoms, or an aralkyl group having 7 to 18 carbon atoms.
- Anions (Y ⁇ ) include halide ions such as chloride ion (Cl ⁇ ), bromide ion (Br ⁇ ), iodine ion (I ⁇ ), carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ), alcoholate (—O ⁇ ) and other acid groups.
- This compound can be obtained as a commercial product, and examples thereof include tetraalkylphosphonium halides such as tetra-n-butylphosphonium halide and tetra-n-propylphosphonium halide, and trialkylbenzyl halides such as triethylbenzylphosphonium halide.
- Phosphonium triphenylmethylphosphonium halide, triphenylmonoalkylphosphonium halide such as triphenylethylphosphonium halide, triphenylbenzylphosphonium halide, tetraphenylphosphonium halide, tritolylmonoarylphosphonium halide, or tritolylmonohalide
- Alkylphosphonium (wherein the halogen atom is a chlorine atom or a bromine atom) can be mentioned.
- triphenylmonoalkylphosphonium halides such as triphenylmethylphosphonium halide and triphenylethylphosphonium halide
- triphenylmonoarylphosphonium halides such as triphenylbenzylphosphonium halide
- halogens such as tritolylmonophenylphosphonium halide
- Tritolylmonoarylphosphonium halides and tritolylmonoalkylphosphonium halides such as tritolylmonomethylphosphonium halides (where the halogen atom is a chlorine atom or a bromine atom) are preferred.
- Phosphines include primary phosphines such as methylphosphine, ethylphosphine, propylphosphine, isopropylphosphine, isobutylphosphine and phenylphosphine, and secondary phosphines such as dimethylphosphine, diethylphosphine, diisopropylphosphine, diisoamylphosphine and diphenylphosphine. , trimethylphosphine, triethylphosphine, triphenylphosphine, methyldiphenylphosphine, dimethylphenylphosphine and the like.
- the compound of formula (D-8) is a tertiary sulfonium salt having a structure of R 35 R 36 R 37 S + Y - .
- R 35 , R 36 and R 37 are, for example, an ethyl group, a propyl group, a butyl group, an alkyl group having 1 to 18 carbon atoms such as cyclohexylmethyl, an aryl group having 6 to 18 carbon atoms such as a phenyl group, or benzyl aralkyl groups having 7 to 18 carbon atoms such as groups, preferably two of the three substituents R 35 to R 37 are unsubstituted phenyl groups or substituted phenyl groups, such as phenyl group and tolyl groups, and the remaining one is an alkyl group with 1 to 18 carbon atoms, an aryl group with 6 to 18 carbon atoms, or an aralkyl group with 7 to 18 carbon atoms.
- the anion (Y ⁇ ) includes halide ions such as chloride ion (Cl ⁇ ), bromide ion (Br ⁇ ), iodine ion (I ⁇ ), carboxylate (—COO ⁇ ), sulfonate (—SO 3 ⁇ ), alcoholate (—O ⁇ ), maleate anion, nitrate anion and the like.
- This compound is commercially available and includes trialkylsulfonium halides such as tri-n-butylsulfonium halide and tri-n-propylsulfonium halide, and dialkylbenzylsulfonium halides such as diethylbenzylsulfonium halide.
- triphenylsulfonium halides halogen atoms are chlorine atoms or bromine atoms
- tri-n-butylsulfonium carboxylate tri-n- trialkylsulfonium carboxylates such as propylsulfonium carboxylate
- dialkylbenzylsulfonium carboxylates such as diethylbenzylsulfonium carboxylate
- diphenylmethylsulfonium carboxylate are mentioned.
- triphenylsulfonium halide and triphenylsulfonium carboxylate can be preferably used.
- Nitrogen-containing silane compounds include imidazole ring-containing silane compounds such as N-(3-triethoxysilipropyl)-4,5-dihydroimidazole.
- the content of the [D] curing catalyst in the silicon-containing resist underlayer film-forming composition is preferably from 0.1 to 0.1 with respect to 100 parts by mass of [A] polysiloxane, from the viewpoint of sufficiently obtaining the effects of the present invention. 30 parts by mass, more preferably 0.5 to 25 parts by mass, and even more preferably 1 to 20 parts by mass.
- the mass ratio ([D]:[B]) of the curing catalyst ([D] component) and [B] component in the silicon-containing resist underlayer film-forming composition is determined from the viewpoint of obtaining the effect of the present invention more sufficiently. , preferably 0.1:1.0 to 1.0:0.1, more preferably 0.2:1.0 to 1.0:0.1, even more preferably 0.5:1.0 to It can be 1.0:0.15.
- the composition for forming a silicon-containing resist underlayer film preferably contains [E] nitric acid.
- [B] Nitric acid may be added during the preparation of the composition for forming a silicon-containing resist underlayer film. What remains in the varnish can also be treated as [E] nitric acid.
- the amount of nitric acid is, for example, 0.0001% by mass to 1% by mass, or 0.001% by mass to 0.001% by mass, based on the total mass of the composition for forming a silicon-containing resist underlayer film. It can be 1 wt%, or 0.005 wt% to 0.05 wt%.
- the silicon-containing resist underlayer film-forming composition preferably contains at least one selected from [F] amines and hydroxides from the viewpoint of sufficiently obtaining the effects of the present invention.
- Amines include ammonia; primary amines such as monomethanolamine, monoethanolamine, monopropanolamine, methylamine, ethylamine, propylamine and butylamine; secondary amines such as dimethylamine, ethylmethylamine and diethylamine; tertiary amines such as , triethylamine, tripropylamine, dimethylethylamine, methyldiisopropylamine, diisopropylethylamine, diethylethanolamine and triethanolamine; amines such as ethylenediamine and tetramethylethylenediamine; cyclic amines such as pyridine and morpholine; be done.
- primary amines such as monomethanolamine, monoethanolamine, monopropanolamine, methylamine, ethylamine, propylamine and butylamine
- secondary amines such as dimethylamine, ethylmethylamine and diethylamine
- Hydroxides include inorganic alkali hydroxides and organic alkali hydroxides.
- inorganic alkali hydroxides include sodium hydroxide and potassium hydroxide.
- organic alkali hydroxides include tetraalkylammonium hydroxide, triarylsulfonium hydroxide, diaryliodonium hydroxide and the like.
- tetraalkylammonium hydroxides include tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrabutylammonium hydroxide and the like.
- triarylsulfonium hydroxide examples include triphenylsulfonium hydroxide and tris(t-butylphenyl)sulfonium hydroxide.
- diaryliodonium hydroxides examples include diphenyliodonium hydroxide and bis(t-butylphenyl)iodonium hydroxide.
- the content of the [F] component in the silicon-containing resist underlayer film-forming composition is preferably 0.05 to 20 parts by mass, more preferably 0.1 to 15 parts by mass, relative to 100 parts by mass of [A] polysiloxane. parts, more preferably 0.5 to 10 parts by weight.
- additives can be added to the composition for forming a silicon-containing resist underlayer film depending on the application of the composition.
- additives include cross-linking agents, cross-linking catalysts, stabilizers (organic acids, water, alcohols, etc.), organic polymers, acid generators, surfactants (nonionic surfactants, anionic surfactants, cationic surfactants, silicon surfactants, fluorine surfactants, UV curable surfactants, etc.), pH adjusters, metal oxides, rheology adjusters, adhesion aids, etc., resist underlayer films, anti-reflection
- Known additives blended in materials (compositions) for forming various films that can be used in the manufacture of semiconductor devices, such as films and films for pattern reversal can be mentioned. Although various additives are exemplified below, they are not limited to these.
- a stabilizer can be added for the purpose of stabilizing the hydrolysis condensate of the hydrolyzable silane mixture, and specific examples thereof include organic acids, water, alcohols, or combinations thereof.
- organic acids include oxalic acid, malonic acid, methylmalonic acid, succinic acid, maleic acid, malic acid, tartaric acid, phthalic acid, citric acid, glutaric acid, lactic acid and salicylic acid. Among them, oxalic acid and maleic acid are preferred.
- the organic acid is added, the amount of addition is 0.1 to 5.0% by mass based on the mass of the hydrolytic condensate of the hydrolyzable silane mixture.
- These organic acids can also act as pH adjusters.
- the amount added is 1 to 20 parts by mass with respect to 100 parts by mass of the composition for forming a silicon-containing resist underlayer film.
- the amount added can be 1 to 20 parts by mass with respect to 100 parts by mass of the composition for forming a silicon-containing resist underlayer film.
- Organic polymer By adding the organic polymer to the composition for forming a silicon-containing resist underlayer film, the dry etching rate (amount of decrease in film thickness per unit time) of the film (resist underlayer film) formed from the composition, or the attenuation A coefficient, a refractive index, etc. can be adjusted.
- the organic polymer is not particularly limited, and is appropriately selected from various organic polymers (condensation polymer and addition polymer) according to the purpose of addition.
- addition polymerization polymers and condensation polymerization polymers such as polyester, polystyrene, polyimide, acrylic polymer, methacrylic polymer, polyvinyl ether, phenol novolak, naphthol novolak, polyether, polyamide, and polycarbonate.
- organic polymers containing aromatic rings such as benzene rings, naphthalene rings, anthracene rings, triazine rings, quinoline rings, and quinoxaline rings and heteroaromatic rings that function as light-absorbing sites are also used when such functions are required. can be preferably used.
- organic polymers include addition polymerizable monomers such as benzyl acrylate, benzyl methacrylate, phenyl acrylate, naphthyl acrylate, anthryl methacrylate, anthryl methyl methacrylate, styrene, hydroxystyrene, benzyl vinyl ether and N-phenylmaleimide. as its structural units, and condensation polymers such as phenol novolacs and naphthol novolacs, but are not limited thereto.
- the polymer When an addition polymer is used as the organic polymer, the polymer may be either a homopolymer or a copolymer.
- Addition-polymerizable monomers are used in the production of addition-polymerized polymers, and specific examples of such addition-polymerizable monomers include acrylic acid, methacrylic acid, acrylic acid ester compounds, methacrylic acid ester compounds, acrylamide compounds, methacrylic Examples include, but are not limited to, amide compounds, vinyl compounds, styrene compounds, maleimide compounds, maleic anhydride, acrylonitrile, and the like.
- acrylic acid ester compounds include methyl acrylate, ethyl acrylate, normal hexyl acrylate, i-propyl acrylate, cyclohexyl acrylate, benzyl acrylate, phenyl acrylate, anthryl methyl acrylate, 2-hydroxyethyl acrylate, 3-chloro-2 - hydroxypropyl acrylate, 2-hydroxypropyl acrylate, 2,2,2-trifluoroethyl acrylate, 2,2,2-trichloroethyl acrylate, 2-bromoethyl acrylate, 4-hydroxybutyl acrylate, 2-methoxyethyl acrylate, tetrahydrofurfuryl acrylate, 2-methyl-2-adamantyl acrylate, 5-acryloyloxy-6-hydroxynorbornene-2-carboxylic-6-lactone, 3-acryloxypropyltriethoxysilane, glycidyl acrylate, etc
- methacrylate compounds include methyl methacrylate, ethyl methacrylate, normal hexyl methacrylate, i-propyl methacrylate, cyclohexyl methacrylate, benzyl methacrylate, phenyl methacrylate, anthrylmethyl methacrylate, 2-hydroxyethyl methacrylate, and 2-hydroxypropyl methacrylate.
- acrylamide compounds include acrylamide, N-methylacrylamide, N-ethylacrylamide, N-benzylacrylamide, N-phenylacrylamide, N,N-dimethylacrylamide, N-anthrylacrylamide and the like. Not limited.
- methacrylamide compounds include methacrylamide, N-methylmethacrylamide, N-ethylmethacrylamide, N-benzylmethacrylamide, N-phenylmethacrylamide, N,N-dimethylmethacrylamide, and N-anthrylmethacrylamide. etc., but not limited to these.
- vinyl compounds include vinyl alcohol, 2-hydroxyethyl vinyl ether, methyl vinyl ether, ethyl vinyl ether, benzyl vinyl ether, vinyl acetate, vinyltrimethoxysilane, 2-chloroethyl vinyl ether, 2-methoxyethyl vinyl ether, vinyl naphthalene, vinyl Examples include, but are not limited to, anthracene.
- styrene compounds include, but are not limited to, styrene, hydroxystyrene, chlorostyrene, bromostyrene, methoxystyrene, cyanostyrene, and acetylstyrene.
- Maleimide compounds include, but are not limited to, maleimide, N-methylmaleimide, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-hydroxyethylmaleimide, and the like.
- a polycondensation polymer when used as the polymer, such a polymer includes, for example, a polycondensation polymer of a glycol compound and a dicarboxylic acid compound.
- Glycol compounds include diethylene glycol, hexamethylene glycol, butylene glycol and the like.
- Dicarboxylic acid compounds include succinic acid, adipic acid, terephthalic acid, maleic anhydride and the like.
- Further examples include, but are not limited to, polyesters such as polypyromellitimide, poly(p-phenylene terephthalamide), polybutylene terephthalate, and polyethylene terephthalate, polyamides, and polyimides.
- the organic polymer contains a hydroxy group, this hydroxy group can undergo a cross-linking reaction with a hydrolyzed condensate or the like.
- the weight average molecular weight of the organic polymer can typically range from 1,000 to 1,000,000.
- the weight average molecular weight is, for example, 3,000 to 300,000, or 5,000 to 5,000. It can be 300,000, or 10,000-200,000, and so on.
- Such organic polymers may be used singly or in combination of two or more.
- the content thereof is determined as appropriate in consideration of the function of the organic polymer, etc., and therefore cannot be categorically defined.
- it can be in the range of 1 to 200% by mass, and from the viewpoint of suppressing precipitation in the composition, for example, 100% by mass or less, preferably 50% by mass or less, more preferably 30% by mass or less. From the viewpoint of sufficiently obtaining the effect, for example, it can be 5% by mass or more, preferably 10% by mass or more, and more preferably 30% by mass or more.
- acid generators include thermal acid generators and photoacid generators, and photoacid generators can be preferably used.
- Photoacid generators include, but are not limited to, onium salt compounds, sulfonimide compounds, disulfonyldiazomethane compounds, and the like.
- the photoacid generator may also function as a curing catalyst, depending on the type of the onium salt compound, such as carboxylates such as nitrates and maleates, and hydrochlorides, which will be described later.
- thermal acid generators include tetramethylammonium nitrate and the like, but are not limited thereto.
- onium salt compounds include diphenyliodonium hexafluorophosphate, diphenyliodonium trifluoromethanesulfonate, diphenyliodonium nonafluoro-normal butanesulfonate, diphenyliodonium perfluoro-normal octane sulfonate, diphenyliodonium camphorsulfonate, bis(4-t-butylphenyl ) iodonium salt compounds such as iodonium camphorsulfonate, bis(4-t-butylphenyl)iodonium trifluoromethanesulfonate, triphenylsulfonium hexafluoroantimonate, triphenylsulfonium nonafluoron-butanesulfonate, triphenylsulfonium camphorsulfonate, triphenylsulfonium Examples include, but are not limited to,
- sulfonimide compounds include N-(trifluoromethanesulfonyloxy)succinimide, N-(nonafluoro-normalbutanesulfonyloxy)succinimide, N-(camphorsulfonyloxy)succinimide, and N-(trifluoromethanesulfonyloxy)naphthalimide. etc., but not limited to these.
- disulfonyldiazomethane compounds include bis(trifluoromethylsulfonyl)diazomethane, bis(cyclohexylsulfonyl)diazomethane, bis(phenylsulfonyl)diazomethane, bis(p-toluenesulfonyl)diazomethane, and bis(2,4-dimethylbenzene).
- sulfonyl)diazomethane methylsulfonyl-p-toluenesulfonyldiazomethane, and the like, but are not limited thereto.
- the content thereof is determined as appropriate in consideration of the type of the acid generator and the like, and cannot be unconditionally defined. It is in the range of 0.01 to 5% by mass, preferably 3% by mass or less, more preferably 1% by mass or less, from the viewpoint of suppressing precipitation of the acid generator in the composition. , from the viewpoint of sufficiently obtaining the effect, it is preferably 0.1% by mass or more, more preferably 0.5% by mass or more.
- the acid generator may be used singly or in combination of two or more, and a photoacid generator and a thermal acid generator may be used in combination.
- Surfactants are effective in suppressing the occurrence of pinholes, striations, etc. when the silicon-containing resist underlayer film-forming composition is applied to a substrate.
- Examples of surfactants include nonionic surfactants, anionic surfactants, cationic surfactants, silicon surfactants, fluorochemical surfactants, and UV curable surfactants.
- polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene oleyl ether, polyoxyethylene octylphenol ether, polyoxyethylene nonylphenol
- Polyoxyethylene alkylaryl ethers such as ethers, polyoxyethylene/polyoxypropylene block copolymers, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, sorbitan tristearate sorbitan fatty acid esters such as polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan trioleate, polyoxyethylene sorbitan tristearate
- Nonionic surfactants such as sorbitan fatty acid esters, trade name Ftop (registered trademark)
- the content thereof is usually 0.0001 to 5% by mass, preferably 0.001, based on the mass of [A] polysiloxane. to 4 mass %, more preferably 0.01 to 3 mass %.
- the rheology modifier mainly improves the fluidity of the composition for forming the silicon-containing resist underlayer film, and particularly in the baking process, improves the uniformity of the film thickness of the formed film and the filling properties of the composition inside the holes.
- phthalic acid derivatives such as dimethyl phthalate, diethyl phthalate, di-i-butyl phthalate, dihexyl phthalate, butyl i-decyl phthalate, di-n-butyl adipate, di-i-butyl adipate, di-i-octyl adipate, Adipic acid derivatives such as octyldecyl adipate, maleic acid derivatives such as di-n-butyl maleate, diethyl maleate and dinonyl maleate, oleic acid derivatives such as methyl oleate, butyl oleate and tetrahydrofurfuryl oleate, or n-butyl stearate and glyceryl stear Examples include stearic acid derivatives such as rate. When these rheology modifiers are used, the amount added is usually less than 30% by mass based on
- the adhesion aid mainly improves the adhesion between the substrate or the resist and the film (resist underlayer film) formed from the composition for forming a silicon-containing resist underlayer film, and particularly suppresses/prevents peeling of the resist during development. added for a purpose.
- chlorosilanes such as trimethylchlorosilane, dimethylvinylchlorosilane, methyldiphenylchlorosilane, and chloromethyldimethylchlorosilane
- alkoxysilanes such as trimethylmethoxysilane, dimethyldiethoxysilane, methyldimethoxysilane, and dimethylvinylethoxysilane
- Disilazane, N,N'-bis(trimethylsilyl)urea dimethyltrimethylsilylamine, silazanes such as trimethylsilylimidazole, ⁇ -chloropropyltrimethoxysilane, ⁇ -aminopropyltriethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane
- Heterocyclic compounds such as other silanes such as benzotriazole, benzimidazole, indazole, imidazole, 2-mercaptobenzimidazole, 2-
- pH adjuster examples include acids having one or more carboxylic acid groups, such as the organic acids exemplified above as stabilizers.
- the amount added is 0.01 to 20 parts by weight, or 0.01 to 10 parts by weight, or 0.01 to 5 parts by weight, relative to 100 parts by weight of [A] polysiloxane. It can be a ratio of parts by mass.
- metal oxides that can be added to the composition for forming a silicon-containing resist underlayer film include tin (Sn), titanium (Ti), aluminum (Al), zirconium (Zr), zinc (Zn), niobium (Nb ), metals such as tantalum (Ta) and W (tungsten) and semimetals such as boron (B), silicon (Si), germanium (Ge), arsenic (As), antimony (Sb), and tellurium (Te) Of these, oxides of one or a combination of two or more can be mentioned, but are not limited to these.
- the concentration of film-forming components in the composition for forming a silicon-containing resist underlayer film is, for example, 0.1 to 50% by mass, 0.1 to 30% by mass, or 0.1 to 25% by mass with respect to the total mass of the composition. %, 0.5 to 20.0 mass %.
- the content of [A] polysiloxane in the film-forming component is usually 20% by mass to 100% by mass, but from the viewpoint of obtaining the effects of the present invention with good reproducibility, the lower limit is preferably 50% by mass. , More preferably 60% by mass, still more preferably 70% by mass, still more preferably 80% by mass, the upper limit is preferably 99% by mass, and the remainder can be used as an additive described later. can.
- the silicon-containing resist underlayer film-forming composition preferably has a pH of 2-5, more preferably a pH of 3-4.
- the composition for forming a silicon-containing resist underlayer film contains at least one selected from [A] polysiloxane, [B] a sulfonic acid compound, and an acid having a pKa of ⁇ 15.0 to 1.2 (for example, sulfuric acid, at least one selected from sulfonic acid compounds), [C] a solvent, and, if desired, other components, can be mixed with the other components.
- a solution containing [A] polysiloxane is prepared in advance, and this solution is added to [B] at least one selected from a sulfonic acid compound and an acid having a pKa of -15.0 to 1.2 (for example, , sulfuric acid, and at least one selected from sulfonic acid compounds), [C] a solvent, and other components.
- the mixing order is not particularly limited.
- [A] a solution containing polysiloxane, [B] a sulfonic acid compound, and at least one selected from acids having a pKa of -15.0 to 1.2 (e.g., sulfuric acid and a sulfonic acid compound at least one selected from), and [C] a solvent may be added and mixed, and other components may be added to the mixture, [A] a solution containing polysiloxane, [B] a sulfonic acid compound, At least one selected from acids having a pKa of -15.0 to 1.2 (e.g., at least one selected from sulfuric acid and sulfonic acid compounds), [C] a solvent, and other components are mixed simultaneously.
- the [C] solvent may be additionally added at the end, or some components that are relatively soluble in the [C] solvent may be left out of the mixture and added at the end.
- a solution in which [A] polysiloxane is well dissolved is prepared in advance, and the composition is prepared using this. preferably prepared.
- [A] Polysiloxane is at least one selected from [B] a sulfonic acid compound mixed together and an acid having a pKa of -15.0 to 1.2 (for example, sulfuric acid and a sulfonic acid compound At least one selected) and [C] depending on the type and amount of the solvent, and the amount and properties of other components, it should be noted that aggregation or precipitation may occur when these are mixed. Further, when preparing a composition using a solution in which [A] polysiloxane is dissolved, [A] polysiloxane is added so that the desired amount of [A] polysiloxane in the finally obtained composition is Also note that the concentration of the solution and the amount to be used need to be determined. In the preparation of the composition, the composition may be appropriately heated as long as the components do not decompose or deteriorate.
- the composition for forming a silicon-containing resist underlayer film may be filtered using a submicrometer-order filter or the like in the middle of manufacturing the composition or after mixing all the components.
- the material of the filter used at this time is not limited, but for example, a nylon filter, a fluororesin filter, or the like can be used.
- composition for forming a silicon-containing resist underlayer film of the present invention can be suitably used as a composition for forming a resist underlayer film used in a lithography process.
- substrates used in the manufacture of precision integrated circuit elements e.g., semiconductor substrates such as silicon wafers coated with silicon oxide films, silicon nitride films or silicon oxynitride films, silicon nitride substrates, quartz substrates, glass substrates (no Alkali glass, low alkali glass, crystallized glass), glass substrates with ITO (indium tin oxide) or IZO (indium zinc oxide) films, plastic (polyimide, PET, etc.) substrates, low dielectric material (low-k material) coated substrate, flexible substrate, etc.] by a suitable coating method such as a spinner or a coater, the silicon-containing resist underlayer film forming composition of the present invention is applied, and then a hot plate By baking using a heating means such as the above, the composition is cured to form a resist underlayer film.
- semiconductor substrates such as silicon wafers coated with silicon oxide films, silicon nitride films or silicon oxynitride films, silicon nitride substrates
- the resist underlayer film refers to a film formed from the composition for forming a silicon-containing resist underlayer film of the present invention.
- the firing conditions are appropriately selected from a firing temperature of 40° C. to 400° C. or 80° C. to 250° C. and a firing time of 0.3 minutes to 60 minutes.
- the firing temperature is 150° C. to 250° C. and the firing time is 0.5 minutes to 2 minutes.
- the film thickness of the resist underlayer film formed here is, for example, 10 nm to 1,000 nm, 20 nm to 500 nm, 50 nm to 300 nm, 100 nm to 200 nm, or 10 to 150 nm.
- a silicon-containing resist underlayer film-forming composition filtered through a nylon filter can be used as the silicon-containing resist underlayer film-forming composition used for forming the resist underlayer film.
- the silicone-containing resist underlayer film-forming composition filtered through a nylon filter means that the silicone-containing resist underlayer film-forming composition was filtered through a nylon filter in the middle of manufacturing the silicon-containing resist underlayer film-forming composition, or after all the components were mixed. Refers to composition.
- the organic underlayer film is formed on the substrate, and then the resist underlayer film is formed thereon.
- the organic underlayer film used here is not particularly limited, and can be arbitrarily selected from those conventionally used in lithography processes.
- the pattern width of the photoresist film is narrowed, and the photoresist film is used to prevent pattern collapse. Even if the film is thinly coated, the substrate can be processed by selecting an appropriate etching gas, which will be described later.
- the resist underlayer film can be processed by using a fluorine-based gas having a sufficiently high etching rate with respect to the photoresist film as an etching gas, and oxygen gas having a sufficiently high etching rate with respect to the resist underlayer film can be used.
- An organic underlayer film can be processed by using a fluorine-based gas as an etching gas, and a substrate can be processed by using a fluorine-based gas having a sufficiently high etching rate with respect to an organic underlayer film as an etching gas. can.
- the substrate and coating method that can be used at this time are the same as those described above.
- a layer of photoresist material is formed on the resist underlayer film.
- the resist film can be formed by a well-known method, that is, by applying a coating-type resist material (resist film-forming composition) onto the resist underlayer film and baking the composition.
- the film thickness of the resist film is, for example, 10 nm to 10,000 nm, 100 nm to 2,000 nm, 200 nm to 1,000 nm, or 30 nm to 200 nm.
- the photoresist material used for the resist film formed on the resist underlayer film is not particularly limited as long as it is sensitive to the light used for exposure (for example, KrF excimer laser, ArF excimer laser, etc.).
- both negative photoresist materials and positive photoresist materials can be used.
- a positive photoresist material composed of a novolac resin and a 1,2-naphthoquinonediazide sulfonic acid ester a chemically amplified photoresist composed of a binder having a group that decomposes with an acid to increase the alkali dissolution rate
- a photoacid generator for example, a positive photoresist material composed of a novolac resin and a 1,2-naphthoquinonediazide sulfonic acid ester, a chemically amplified photoresist composed of a binder having a group that decomposes with an acid to increase the alkali dissolution rate.
- a chemically amplified photoresist material composed of a low-molecular-weight compound, an alkali-soluble binder, and a photoacid generator that decomposes with an acid to increase the alkali dissolution rate of the photoresist material
- a chemically amplified photoresist material composed of a binder having a group that causes a reaction, a low-molecular-weight compound that is decomposed by an acid to increase the alkali dissolution rate of the photoresist material, and a photoacid generator.
- a resist film for electron beam lithography also referred to as an electron beam resist film
- a resist film for EUV lithography also referred to as an EUV resist film
- the composition for forming a silicon-containing resist underlayer film of the present invention can be used for forming a resist underlayer film for electron beam lithography or for forming a resist underlayer film for EUV lithography. It is particularly suitable as a composition for forming a resist underlayer film for EUV lithography.
- the electron beam resist material for forming the electron beam resist film either a negative material or a positive material can be used.
- Specific examples thereof include a chemically amplified resist material composed of an acid generator and a binder having a group that is decomposed by an acid to change the alkali dissolution rate;
- a chemically amplified resist material composed of a low-molecular-weight compound that changes the dissolution rate, a binder having a group that decomposes with an acid generator and an acid to change the alkali dissolution rate, and a binder that decomposes with the acid to change the alkali dissolution rate of the resist material.
- non-chemically amplified resist materials made of binders Even when these electron beam resist materials are used, a resist film pattern can be formed in the same manner as when a photoresist material is used with an electron beam as the irradiation source.
- the EUV resist material for forming the EUV resist film a methacrylate resin-based resist material can be used as the EUV resist film.
- the resist film formed on the resist underlayer film is exposed through a predetermined mask (reticle).
- KrF excimer laser (wavelength: 248 nm), ArF excimer laser (wavelength: 193 nm), F2 excimer laser ( wavelength: 157 nm), EUV (wavelength: 13.5 nm), electron beam, etc. can be used for exposure.
- a post-exposure bake can be performed, if desired.
- the post-exposure heating is performed under conditions appropriately selected from a heating temperature of 70° C. to 150° C. and a heating time of 0.3 minutes to 10 minutes.
- a developer for example, an alkaline developer
- a developer for example, an alkaline developer
- alkali metal hydroxides such as potassium hydroxide and sodium hydroxide
- alkaline aqueous solutions such as aqueous solutions of amines such as amine, propylamine and ethylenediamine. Further, a surfactant or the like can be added to these developers.
- the development conditions are appropriately selected from a temperature of 5 to 50° C. and a time of 10 to 600 seconds.
- an organic solvent can be used as a developer, and development is performed with the developer (solvent) after exposure.
- the developer solvent
- the photoresist film in the unexposed portions is removed to form a pattern of the photoresist film.
- Examples of the developer (organic solvent) include methyl acetate, butyl acetate, ethyl acetate, isopropyl acetate, amyl acetate, isoamyl acetate, ethyl methoxyacetate, ethyl ethoxyacetate, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, Ethylene glycol monopropyl ether acetate, ethylene glycol monobutyl ether acetate, ethylene glycol monophenyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monopropyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monophenyl ether acetate, diethylene glycol monobutyl ether acetate, diethylene glycol mono Ethyl ether acetate, 2-methoxybutyl acetate, 3-methoxybutyl
- the resist underlayer film (intermediate layer) is removed, and then the patterned photoresist film and patterned resist underlayer film (intermediate layer) are removed.
- the organic underlayer film (lower layer) is removed.
- the substrate is processed using the patterned resist underlayer film (intermediate layer) and the patterned organic underlayer film (lower layer) as protective films.
- the removal (patterning) of the resist underlayer film (intermediate layer), which is performed using the pattern of the resist film (upper layer) as a protective film, is performed by dry etching using tetrafluoromethane (CF 4 ) and perfluorocyclobutane (C 4 F 8 ).
- perfluoropropane ( C3F8 ) trifluoromethane, carbon monoxide, argon, oxygen, nitrogen, sulfur hexafluoride, difluoromethane, nitrogen trifluoride, chlorine trifluoride, chlorine, trichloroborane and dichloroborane, etc. of gas can be used.
- a halogen-based gas for the dry etching of the resist underlayer film.
- a resist film photoresist film
- a resist underlayer film containing a large amount of silicon atoms is rapidly removed by a halogen-based gas. Therefore, reduction in the thickness of the photoresist film due to dry etching of the resist underlayer film can be suppressed. As a result, it becomes possible to use a thin photoresist film. Therefore , the dry etching of the resist underlayer film is preferably performed using a fluorine - based gas. 8 ), trifluoromethane, difluoromethane (CH 2 F 2 ), and the like, but are not limited to these.
- patterned resist film (top layer) and patterned (with patterned resist film (top layer) if remaining) The removal (patterning) of the organic underlayer film (lower layer), which is performed using the resist underlayer film (intermediate layer) as a protective film, is performed using an oxygen-based gas (oxygen gas, oxygen/carbonyl sulfide (COS) mixed gas, etc.) It is preferably performed by dry etching with. This is because the resist underlayer film of the present invention containing a large amount of silicon atoms is difficult to remove by dry etching with an oxygen-based gas.
- oxygen-based gas oxygen gas, oxygen/carbonyl sulfide (COS) mixed gas, etc.
- the (semiconductor) substrate is processed (patterned) using a patterned resist underlayer film (intermediate layer) and, if desired, a patterned organic underlayer film (lower layer) as a protective film. It is preferably done by etching.
- fluorine-based gases include tetrafluoromethane (CF 4 ), perfluorocyclobutane (C 4 F 8 ), perfluoropropane (C 3 F 8 ), trifluoromethane, and difluoromethane (CH 2 F 2 ). mentioned.
- removal of the resist underlayer film may be performed. Removal of the resist underlayer film can be performed by dry etching or wet etching. The dry etching of the resist underlayer film is preferably performed with a fluorine - based gas as mentioned in the patterning. 8 ), trifluoromethane, difluoromethane (CH 2 F 2 ), and the like, but are not limited to these.
- Chemicals used for wet etching of the resist underlayer film include dilute hydrofluoric acid (hydrofluoric acid), buffered hydrofluoric acid (mixed solution of HF and NH 4 F), aqueous solution containing hydrochloric acid and hydrogen peroxide (SC -2 chemical solution), an aqueous solution containing sulfuric acid and hydrogen peroxide (SPM chemical solution), an aqueous solution containing hydrofluoric acid and hydrogen peroxide (FPM chemical solution), and an aqueous solution containing ammonia and hydrogen peroxide (SC-1 chemical solution) and other alkaline solutions.
- hydrofluoric acid hydrofluoric acid
- buffered hydrofluoric acid mixed solution of HF and NH 4 F
- SC -2 chemical solution aqueous solution containing hydrochloric acid and hydrogen peroxide
- SPM chemical solution sulfuric acid and hydrogen peroxide
- FPM chemical solution aqueous solution containing hydrofluoric acid and hydrogen peroxide
- SC-1 chemical solution a
- ammonia hydrogen peroxide solution obtained by mixing ammonia, hydrogen peroxide solution and water, ammonia, tetramethylammonium hydroxide (TMAH), tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, choline hydroxide, benzyltrimethylammonium hydroxide, benzyltriethylammonium hydroxide, DBU (diazabicycloundecene), DBN (diazabicyclononene), hydroxylamine, 1-butyl-1 -methylpyrrolidinium hydroxide, 1-propyl-1-methylpyrrolidinium hydroxide, 1-butyl-1-methylpiperidinium hydroxide, 1-propyl-1-methylpiperidinium hydroxide, mepicquat Mention may be made of aqueous
- an organic antireflection film can be formed on the upper layer of the resist underlayer film before forming the resist film.
- the antireflection coating composition used there is not particularly limited, and can be used by arbitrarily selecting, for example, those conventionally used in lithographic processes. , a spinner, or a coater, and baking to form the antireflection film.
- the substrate to which the silicon-containing resist underlayer film-forming composition is applied may have an organic or inorganic antireflection film formed on its surface by a CVD method or the like.
- An underlayer film can also be formed.
- the resist underlayer film of the present invention is formed thereon after forming an organic underlayer film on the substrate, the substrate to be used has an organic or inorganic antireflection film formed on its surface by a CVD method or the like. may have.
- the resist underlayer film formed from the composition for forming a silicon-containing resist underlayer film may also absorb light. In such a case, it can function as an antireflection film having the effect of preventing reflected light from the substrate. Furthermore, the resist underlayer film is a layer for preventing interaction between the substrate and the resist film (photoresist film, etc.), and prevents adverse effects on the substrate of materials used for the resist film or substances generated when the resist film is exposed to light.
- It is used as a layer having a function to prevent diffusion, a layer having a function to prevent diffusion of substances generated from the substrate during heating and baking into the resist film, and a barrier layer for reducing the poisoning effect of the resist film due to the dielectric layer of the semiconductor substrate. is also possible.
- the resist underlayer film can be applied to a substrate in which via holes used in the dual damascene process are formed, and can be used as a filling material (embedding material) capable of filling the holes without gaps. It can also be used as a planarizing material for planarizing the uneven surface of a semiconductor substrate.
- the resist underlayer film of the present invention as an underlayer film of the EUV resist film, has a function as a hard mask. For example, UV (ultraviolet) light and DUV (deep ultraviolet) light (:ArF light, KrF light) can be prevented from being reflected from the substrate or the interface.
- the composition for forming a silicon-containing resist underlayer film of the present invention can be suitably used for forming an underlayer antireflection film of an EUV resist film. That is, it can efficiently prevent reflection as a lower layer of the EUV resist film.
- the process can be performed in the same manner as for the photoresist underlayer film.
- the semiconductor substrate can be suitably processed. Further, as described above, the step of forming an organic underlayer film, the step of forming a resist underlayer film on the organic underlayer film using the silicon-containing resist underlayer film-forming composition of the present invention, and the step of forming the resist underlayer film According to the method for manufacturing a semiconductor device, which includes the step of forming a resist film on the film, it is possible to process a semiconductor substrate with high accuracy and reproducibility, so that stable manufacture of semiconductor devices can be expected.
- the equipment and conditions used for analyzing the physical properties of the samples are as follows.
- the molecular weight of the polysiloxane used in the present invention is the molecular weight obtained in terms of polystyrene by GPC analysis.
- GPC measurement conditions include, for example, a GPC device (trade name HLC-8220GPC, manufactured by Tosoh Corporation), a GPC column (trade name Shodex (registered trademark) KF803L, KF802, KF801, manufactured by Showa Denko KK), and a column temperature of 40°C.
- the eluent (elution solvent) is tetrahydrofuran
- the flow rate (flow rate) is 1.0 mL/min
- the standard sample is polystyrene (manufactured by Showa Denko KK).
- 1 H-NMR Evaluation was performed using a nuclear magnetic resonance apparatus 1 H-NMR (400 MHz) manufactured by JEOL and d6-acetone as a solvent.
- Amount of residual nitric acid The amount of nitric acid remaining in the system was measured by ion chromatography.
- reaction by-products ethanol, methanol and water, were distilled off under reduced pressure and concentrated to obtain a hydrolyzed condensate (polymer) solution.
- Propylene glycol monoethyl ether was further added to the obtained solution, and the concentration was adjusted so that the solvent ratio of 100% propylene glycol monoethyl ether was 20% by mass in terms of solid residue at 140 ° C., and a nylon filter (pore size 0 .1 ⁇ m).
- the obtained polymer contained polysiloxane having a structure represented by the following formula, and had a weight average molecular weight of 3,000 in terms of polystyrene by GPC. Also, the amount of capping with propylene glycol monoethyl ether was 3 mol % with respect to Si atoms by 1 H-NMR. The amount of residual nitric acid in the polymer solution was 1,200 ppm.
- the obtained polymer contained polysiloxane having a structure represented by the following formula, and had a weight average molecular weight of Mw 2,800 in terms of polystyrene by GPC. Also, the amount of capping with propylene glycol monoethyl ether was 3 mol % with respect to Si atoms by 1 H-NMR. The amount of residual nitric acid in the polymer solution was 1,200 ppm.
- the obtained polymer contained polysiloxane having a structure represented by the following formula, and had a weight average molecular weight of Mw 2,300 in terms of polystyrene by GPC. Also, the amount of capping with propylene glycol monoethyl ether was 2 mol % with respect to Si atoms by 1 H-NMR. The amount of residual nitric acid in the polymer solution was 1,200 ppm.
- the obtained polymer contained polysiloxane having a structure represented by the following formula, and had a weight average molecular weight of Mw 2,600 in terms of polystyrene by GPC. Also, the amount of capping with propylene glycol monoethyl ether was 3 mol % with respect to Si atoms by 1 H-NMR. The amount of residual nitric acid in the polymer solution was 1,200 ppm.
- reaction by-products, ethanol and water were distilled off under reduced pressure and concentrated to obtain a hydrolyzed condensate (polymer) solution.
- Propylene glycol monoethyl ether was further added to the obtained solution, and the concentration was adjusted so that the solvent ratio of 100% propylene glycol monoethyl ether was 20% by mass in terms of solid residue at 140 ° C., and a nylon filter (pore size 0 .1 ⁇ m).
- the resulting polymer contained polysiloxane having a structure represented by the following formula, and had a weight average molecular weight of Mw 3,200 in terms of polystyrene by GPC. Also, the amount of capping with propylene glycol monoethyl ether was 4 mol % with respect to Si atoms by 1 H-NMR. The amount of residual nitric acid in the polymer solution was 1,200 ppm.
- reaction by-products ethanol, methanol and water, were distilled off under reduced pressure and concentrated to obtain a hydrolyzed condensate (polymer) solution.
- Propylene glycol monoethyl ether was further added to the obtained solution, and the concentration was adjusted so that the solvent ratio of 100% propylene glycol monoethyl ether was 20% by mass in terms of solid residue at 140 ° C., and a nylon filter (pore size 0 .1 ⁇ m).
- the resulting polymer contained polysiloxane having a structure represented by the following formula, and had a weight average molecular weight of Mw 3,100 in terms of polystyrene by GPC.
- the amount of capping with propylene glycol monoethyl ether was 3 mol % with respect to Si atoms by 1 H-NMR.
- the amount of residual nitric acid in the polymer solution was 1,200 ppm.
- reaction by-products ethanol, methanol and water, were distilled off under reduced pressure and concentrated to obtain a hydrolyzed condensate (polymer) solution.
- Propylene glycol monoethyl ether was further added to the obtained solution, and the concentration was adjusted so that the solvent ratio of 100% propylene glycol monoethyl ether was 20% by mass in terms of solid residue at 140 ° C., and a nylon filter (pore size 0 .1 ⁇ m).
- the resulting polymer contained polysiloxane having a structure represented by the following formula, and had a weight average molecular weight of Mw 3,000 in terms of polystyrene by GPC. Also, the amount of capping with propylene glycol monoethyl ether was 3 mol % with respect to Si atoms by 1 H-NMR. The amount of residual nitric acid in the polymer solution was 1,200 ppm.
- reaction by-products ethanol, methanol and water, were distilled off under reduced pressure and concentrated to obtain a hydrolyzed condensate (polymer) solution.
- Propylene glycol monomethyl ether was further added to the obtained solution, and the concentration was adjusted so that the solvent ratio of 100% propylene glycol monomethyl ether was 20% by mass in terms of solid residue at 140 ° C., and filtered through a nylon filter (pore size 0.1 ⁇ m). ) was filtered.
- the resulting polymer contained polysiloxane having a structure represented by the following formula, and had a weight average molecular weight of Mw 3,000 in terms of polystyrene by GPC. Also, the amount of capping with propylene glycol monomethyl ether was 4 mol % with respect to Si atoms by 1 H-NMR. The amount of residual nitric acid in the polymer solution was 1,200 ppm.
- composition to be applied to resist pattern Each composition to be applied to a resist pattern was prepared by mixing at the ratios shown in Table 1-2 and filtering through a 0.1 ⁇ m fluororesin filter. Each addition amount in Tables 1-1 and 1-2 is shown in parts by mass.
- the hydrolytic condensate (polymer) is prepared as a solution containing the condensate obtained in Synthesis Example, but the addition ratio of the polymer in Tables 1-1 and 1-2 is that of the polymer solution. The added amount of the polymer itself is shown instead of the added amount.
- DIW ultrapure water
- PGEE propylene glycol monoethyl ether
- PGME propylene glycol monomethyl ether
- TPSNO3 triphenylsulfonium nitrate
- TPSML triphenylsulfonium maleate
- TPSTfAc triphenylsulfonium trifluoroacetate
- IMTEOS triethoxysilylpropyl-4,5-dihydroimidazole
- TPSAc triphenylsulfonium acetate
- BTEAC benzyltriethylammonium chloride salt
- TPSCl triphenylsulfonium chloride salt
- Examples 1-15 and Comparative Example 1 further include nitric acid contained in the polymer solutions prepared in Synthesis Examples 1-8.
- the obtained solution was filtered using a polyethylene microfilter with a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter with a pore size of 0.05 ⁇ m to prepare a composition for forming an organic underlayer film. .
- a resist pattern was formed using each of the compositions obtained in Examples 2 to 9 and Comparative Example 1 in the same procedure.
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Abstract
Description
近年、半導体デバイスの高集積度化が進み、使用される活性光線もKrFエキシマレーザー(248nm)からArFエキシマレーザー(193nm)へと短波長化される傾向にある。活性光線の短波長化に伴い、活性光線の半導体基板からの反射の影響が大きな問題となる中、フォトレジストと被加工基板の間に反射防止膜(Bottom Anti-Reflective Coating、BARC)と呼ばれるレジスト下層膜を設ける方法が広く適用されるようになってきた。
[1] [A]成分:ポリシロキサン
[B]成分:スルホン酸化合物と、pKaが-15.0~1.2の酸とから選ばれる少なくとも1種、及び
[C]成分:溶媒
を含有する、シリコン含有レジスト下層膜形成用組成物。
[2] [B]成分が、硫酸と、スルホン酸化合物とから選ばれる少なくとも1種である、[1]に記載のシリコン含有レジスト下層膜形成用組成物。
[3] [D]成分:硬化触媒を更に含有する、[1]に記載のシリコン含有レジスト下層膜形成用組成物。
[4] 前記[D]成分と前記[B]成分との質量比率([D]:[B])が、0.1:1.0~1.0:0.1である、[3]に記載のシリコン含有レジスト下層膜形成用組成物。
[5] 前記[B]成分が、ヒドロキシ基を有するスルホン酸化合物を含有する、[1]~[4]のいずれかに記載のシリコン含有レジスト下層膜形成用組成物。
[6] 前記[A]成分が、シラノール基の少なくとも一部がアルコール変性された又はアセタール保護されたポリシロキサン変性物を含む、[1]~[5]のいずれかに記載のシリコン含有レジスト下層膜形成用組成物。
[7] 前記[C]成分が、アルコール系溶媒を含有する、[1]~[6]のいずれかに記載のシリコン含有レジスト下層膜形成用組成物。
[8] 前記[C]成分が、プロピレングリコールモノアルキルエーテルを含有する、[7]に記載のシリコン含有レジスト下層膜形成用組成物。
[9] [E]成分:硝酸を更に含有する、[1]~[8]のいずれかに記載のシリコン含有レジスト下層膜形成用組成物。
[10] [F]成分:アミンと水酸化物とから選ばれる少なくとも1種を更に含有する、[1]~[9]のいずれかに記載のシリコン含有レジスト下層膜形成用組成物。
[11] 前記[C]成分が、水を含有する、[1]~[10]のいずれかに記載のシリコン含有レジスト下層膜形成用組成物。
[12] EUVリソグラフィー用レジスト下層膜用である、[1]~[11]のいずれかに記載のシリコン含有レジスト下層膜形成用組成物。
[13] [1]~[12]のいずれかに記載のシリコン含有レジスト下層膜形成用組成物の硬化物である、レジスト下層膜。
[14] 半導体基板と、[13]に記載のレジスト下層膜とを備える半導体加工用基板。
[15] 基板上に、有機下層膜を形成する工程と、
前記有機下層膜の上に、[1]~[12]のいずれかに記載のシリコン含有レジスト下層膜形成用組成物を用いてレジスト下層膜を形成する工程と、
前記レジスト下層膜の上に、レジスト膜を形成する工程と、
を含む、半導体素子の製造方法。
[16] 前記レジスト下層膜を形成する工程において、ナイロンフィルタろ過したシリコン含有レジスト下層膜形成用組成物を使用する、
[15]に記載の半導体素子の製造方法。
[17] 半導体基板上に有機下層膜を形成する工程と、
前記有機下層膜の上に、[1]~[12]のいずれかに記載のシリコン含有レジスト下層膜形成用組成物を塗布し、焼成して、レジスト下層膜を形成する工程と、
前記レジスト下層膜の上に、レジスト膜形成用組成物を塗布し、レジスト膜を形成する工程と、
前記レジスト膜を露光、現像し、レジストパターンを得る工程と、
前記レジストパターンをマスクに用い、前記レジスト下層膜をエッチングする工程と、
パターン化された前記レジスト下層膜をマスクとして用い、前記有機下層膜をエッチングする工程と、
を含む、パターン形成方法。
[18] 前記有機下層膜をエッチングする工程の後に、薬液を用いた湿式法により前記シリコン含有レジスト下層膜を除去する工程、
を更に含む、[17]に記載のパターン形成方法。
そして本発明によれば、さらなる微細化が求められるリソグラフィー工程において好適に用いることができるシリコン含有レジスト下層膜形成用組成物を提供できる。
本発明のシリコン含有レジスト下層形成用組成物は、[A]成分としてのポリシロキサン、[B]成分としてのスルホン酸化合物と、pKaが-15.0~1.2の酸とから選ばれる少なくとも1種、及び[C]成分としての溶媒を含有し、更に必要に応じて、その他の成分を含有する。
本発明者らは、ポリシロキサンを含有するシリコン含有レジスト下層形成用組成物に、[B]成分としてのスルホン酸化合物と、pKaが-15.0~1.2の酸とから選ばれる少なくとも1種(例えば、硫酸と、スルホン酸化合物とから選ばれる少なくとも1種)を含めることで、薬液を用いたウェットエッチングによる方法でも除去可能であり、また高いウェットエッチング速度を実現でき、リソグラフィー特性にも優れるレジスト下層膜を形成できることを見出した。
シリコン含有レジスト下層形成用組成物にスルホン酸塩、スルホン酸エステル、ジフェニルスルホンなどが使用できることは知られていた。その一方で、硫酸やスルホン酸化合物を使用した場合には、エッチング特性が低下することがあった。しかし、本発明者らは、スルホン酸化合物、及びpKaが-15.0~1.2の酸(例えば、硫酸やスルホン酸化合物)を使用する場合でも、薬液を用いたウェットエッチングによる方法でも除去可能であり、また高いウェットエッチング速度を実現でき、リソグラフィー特性にも優れるレジスト下層膜を形成できることを見出した。
[A]成分としてのポリシロキサンは、シロキサン結合を有するポリマーである限り特に限定されない。
またポリシロキサンは、一例として加水分解性シランの加水分解縮合物を含み、加水分解縮合物が有するシラノール基の少なくとも一部がアルコール変性された又はアセタール保護された変性ポリシロキサンを含んでいてもよい。加水分解縮合物に係る加水分解性シランは、一種又は二種以上の加水分解性シランを含むことができる。
またポリシロキサンは、かご型、ラダー型、直鎖型、及び分岐型のいずれの主鎖を有する構造であるものとすることができる。さらにポリシロキサンとして、市販のポリシロキサンを使用することができる。
なお、本明細書において、「加水分解性シラン」を単に「シラン化合物」とも称することがある。
またR2は、ケイ素原子に結合する基又は原子であって、互いに独立して、アルコキシ基、アラルキルオキシ基、アシルオキシ基、又はハロゲン原子を表す。
aは0~3の整数を表す。
アルキル基は、直鎖状、分枝鎖状、環状のいずれでよく、その炭素数は、特に限定されるものではないが、好ましくは40以下、より好ましくは30以下、より一層好ましくは20以下、更に好ましくは10以下である。
アルキル基として、直鎖状の又は分枝鎖状アルキル基の具体例としては、メチル基、エチル基、n-プロピル基、i-プロピル基、n-ブチル基、i-ブチル基、s-ブチル基、t-ブチル基、n-ペンチル基、1-メチル-n-ブチル基、2-メチル-n-ブチル基、3-メチル-n-ブチル基、1,1-ジメチル-n-プロピル基、1,2-ジメチル-n-プロピル基、2,2-ジメチル-n-プロピル基、1-エチル-n-プロピル基、n-ヘキシル基、1-メチル-n-ペンチル基、2-メチル-n-ペンチル基、3-メチル-n-ペンチル基、4-メチル-n-ペンチル基、1,1-ジメチル-n-ブチル基、1,2-ジメチル-n-ブチル基、1,3-ジメチル-n-ブチル基、2,2-ジメチル-n-ブチル基、2,3-ジメチル-n-ブチル基、3,3-ジメチル-n-ブチル基、1-エチル-n-ブチル基、2-エチル-n-ブチル基、1,1,2-トリメチル-n-プロピル基、1,2,2-トリメチル-n-プロピル基、1-エチル-1-メチル-n-プロピル基及び1-エチル-2-メチル-n-プロピル基等が挙げられる。
なお、本明細書において、「i」は「iso」、「s」は「sec」、「t」は「tert」を意味する。
例えばアリ-ル基として炭素数6~20のアリール基が挙げられ、一例としてフェニル基、1-ナフチル基、2-ナフチル基、1-アントリル基、2-アントリル基、9-アントリル基、1-フェナントリル基、2-フェナントリル基、3-フェナントリル基、4-フェナントリル基、9-フェナントリル基、1-ナフタセニル基、2-ナフタセニル基、5-ナフタセニル基、2-クリセニル基、1-ピレニル基、2-ピレニル基、ペンタセニル基、ベンゾピレニル基、トリフェニレニル基;ビフェニル-2-イル基(o-ビフェニリル基)、ビフェニル-3-イル基(m-ビフェニリル基)、ビフェニル-4-イル基(p-ビフェニリル基)、パラテルフェニル-4-イル基、メタテルフェニル-4-イル基、オルトテルフェニル-4-イル基、1,1’-ビナフチル-2-イル基、2,2’-ビナフチル-1-イル基等が挙げられるが、これらに限定されない。
アラルキル基の具体例としては、フェニルメチル基(ベンジル基)、2-フェニルエチレン基、3-フェニル-n-プロピル基、4-フェニル-n-ブチル基、5-フェニル-n-ペンチル基、6-フェニル-n-ヘキシル基、7-フェニル-n-ヘプチル基、8-フェニル-n-オクチル基、9-フェニル-n-ノニル基、10-フェニル-n-デシル基等が挙げられるが、これらに限定されない。
ハロゲン原子としては、フッ素原子、塩素原子、臭素原子、ヨウ素原子等が挙げられる。
ハロゲン化アルキル基の具体例としては、モノフルオロメチル基、ジフルオロメチル基、トリフルオロメチル基、ブロモジフルオロメチル基、2-クロロエチル基、2-ブロモエチル基、1,1-ジフルオロエチル基、2,2,2-トリフルオロエチル基、1,1,2,2-テトラフルオロエチル基、2-クロロ-1,1,2-トリフルオロエチル基、ペンタフルオロエチル基、3-ブロモプロピル基、2,2,3,3-テトラフルオロプロピル基、1,1,2,3,3,3-ヘキサフルオロプロピル基、1,1,1,3,3,3-ヘキサフルオロプロパン-2-イル基、3-ブロモ-2-メチルプロピル基、4-ブロモブチル基、パーフルオロペンチル基等が挙げられるが、これらに限定されない。
ハロゲン化アリール基の具体例としては、2-フルオロフェニル基、3-フルオロフェニル基、4-フルオロフェニル基、2,3-ジフルオロフェニル基、2,4-ジフルオロフェニル基、2,5-ジフルオロフェニル基、2,6-ジフルオロフェニル基、3,4-ジフルオロフェニル基、3,5-ジフルオロフェニル基、2,3,4-トリフルオロフェニル基、2,3,5-トリフルオロフェニル基、2,3,6-トリフルオロフェニル基、2,4,5-トリフルオロフェニル基、2,4,6-トリフルオロフェニル基、3,4,5-トリフルオロフェニル基、2,3,4,5-テトラフルオロフェニル基、2,3,4,6-テトラフルオロフェニル基、2,3,5,6-テトラフルオロフェニル基、ペンタフルオロフェニル基、2-フルオロ-1-ナフチル基、3-フルオロ-1-ナフチル基、4-フルオロ-1-ナフチル基、6-フルオロ-1-ナフチル基、7-フルオロ-1-ナフチル基、8-フルオロ-1-ナフチル基、4,5-ジフルオロ-1-ナフチル基、5,7-ジフルオロ-1-ナフチル基、5,8-ジフルオロ-1-ナフチル基、5,6,7,8-テトラフルオロ-1-ナフチル基、ヘプタフルオロ-1-ナフチル基、1-フルオロ-2-ナフチル基、5-フルオロ-2-ナフチル基、6-フルオロ-2-ナフチル基、7-フルオロ-2-ナフチル基、5,7-ジフルオロ-2-ナフチル基、ヘプタフルオロ-2-ナフチル基等が挙げられ、またこれらの基におけるフッ素原子(フルオロ基)が塩素原子(クロロ基)、臭素原子(ブロモ基)、ヨウ素原子(ヨード基)に任意に置換された基が挙げられるが、これらに限定されない。
ハロゲン化アラルキル基の具体例としては、2-フルオロベンジル基、3-フルオロベンジル基、4-フルオロベンジル基、2,3-ジフルオロベンジル基、2,4-ジフルオロベンジル基、2,5-ジフルオロベンジル基、2,6-ジフルオロベンジル基、3,4-ジフルオロベンジル基、3,5-ジフルオロベンジル基、2,3,4-トリフルオロベンジル基、2,3,5-トリフルオロベンジル基、2,3,6-トリフルオロベンジル基、2,4,5-トリフルオロベンジル基、2,4,6-トリフルオロベンジル基、2,3,4,5-テトラフルオロベンジル基、2,3,4,6-テトラフルオロベンジル基、2,3,5,6-テトラフルオロベンジル基、2,3,4,5,6-ペンタフルオロベンジル基等が挙げられ、またこれらの基におけるフッ素原子(フルオロ基)が塩素原子(クロロ基)、臭素原子(ブロモ基)、ヨウ素原子(ヨード基)に任意に置換された基が挙げられるが、これらに限定されない。
直鎖状の又は分枝状のアルコキシ基としては、例えばメトキシ基、エトキシ基、n-プロポキシ基、i-プロポキシ基、n-ブトキシ基、i-ブトキシ基、s-ブトキシ基、t-ブトキシ基、n-ペンチロキシ基、1-メチル-n-ブトキシ基、2-メチル-n-ブトキシ基、3-メチル-n-ブトキシ基、1,1-ジメチル-n-プロポキシ基、1,2-ジメチル-n-プロポキシ基、2,2-ジメチル-n-プロポキシ基、1-エチル-n-プロポキシ基、n-ヘキシロキシ基、1-メチル-n-ペンチロキシ基、2-メチル-n-ペンチロキシ基、3-メチル-n-ペンチロキシ基、4-メチル-n-ペンチロキシ基、1,1-ジメチル-n-ブトキシ基、1,2-ジメチル-n-ブトキシ基、1,3-ジメチル-n-ブトキシ基、2,2-ジメチル-n-ブトキシ基、2,3-ジメチル-n-ブトキシ基、3,3-ジメチル-n-ブトキシ基、1-エチル-n-ブトキシ基、2-エチル-n-ブトキシ基、1,1,2-トリメチル-n-プロポキシ基、1,2,2-トリメチル-n-プロポキシ基、1-エチル-1-メチル-n-プロポキシ基及び1-エチル-2-メチル-n-プロポキシ基等が挙げられる。
また環状のアルコキシ基としては、例えばシクロプロポキシ基、シクロブトキシ基、1-メチル-シクロプロポキシ基、2-メチル-シクロプロポキシ基、シクロペンチロキシ基、1-メチル-シクロブトキシ基、2-メチル-シクロブトキシ基、3-メチル-シクロブトキシ基、1,2-ジメチル-シクロプロポキシ基、2,3-ジメチル-シクロプロポキシ基、1-エチル-シクロプロポキシ基、2-エチル-シクロプロポキシ基、シクロヘキシロキシ基、1-メチル-シクロペンチロキシ基、2-メチル-シクロペンチロキシ基、3-メチル-シクロペンチロキシ基、1-エチル-シクロブトキシ基、2-エチル-シクロブトキシ基、3-エチル-シクロブトキシ基、1,2-ジメチル-シクロブトキシ基、1,3-ジメチル-シクロブトキシ基、2,2-ジメチル-シクロブトキシ基、2,3-ジメチル-シクロブトキシ基、2,4-ジメチル-シクロブトキシ基、3,3-ジメチル-シクロブトキシ基、1-n-プロピル-シクロプロポキシ基、2-n-プロピル-シクロプロポキシ基、1-i-プロピル-シクロプロポキシ基、2-i-プロピル-シクロプロポキシ基、1,2,2-トリメチル-シクロプロポキシ基、1,2,3-トリメチル-シクロプロポキシ基、2,2,3-トリメチル-シクロプロポキシ基、1-エチル-2-メチル-シクロプロポキシ基、2-エチル-1-メチル-シクロプロポキシ基、2-エチル-2-メチル-シクロプロポキシ基及び2-エチル-3-メチル-シクロプロポキシ基等が挙げられる。
アルコキシアリール基の具体例としては、2-メトキシフェニル基、3-メトキシフェニル基、4-メトキシフェニル基、2-(1-エトキシ)フェニル基、3-(1-エトキシ)フェニル基、4-(1-エトキシ)フェニル基、2-(2-エトキシ)フェニル基、3-(2-エトキシ)フェニル基、4-(2-エトキシ)フェニル基、2-メトキシナフタレン-1-イル基、3-メトキシナフタレン-1-イル基、4-メトキシナフタレン-1-イル基、5-メトキシナフタレン-1-イル基、6-メトキシナフタレン-1-イル基、7-メトキシナフタレン-1-イル基等が挙げられるが、これらに限定されない。
アルコキシアラルキル基の具体例としては、3-(メトキシフェニル)ベンジル基、4-(メトキシフェニル)ベンジル基等が挙げられるが、これらに限定されない。
アルケニル基の具体例としては、エテニル基(ビニル基)、1-プロペニル基、2-プロペニル基、1-メチル-1-エテニル基、1-ブテニル基、2-ブテニル基、3-ブテニル基、2-メチル-1-プロペニル基、2-メチル-2-プロペニル基、1-エチルエテニル基、1-メチル-1-プロペニル基、1-メチル-2-プロペニル基、1-ペンテニル基、2-ペンテニル基、3-ペンテニル基、4-ペンテニル基、1-n-プロピルエテニル基、1-メチル-1-ブテニル基、1-メチル-2-ブテニル基、1-メチル-3-ブテニル基、2-エチル-2-プロペニル基、2-メチル-1-ブテニル基、2-メチル-2-ブテニル基、2-メチル-3-ブテニル基、3-メチル-1-ブテニル基、3-メチル-2-ブテニル基、3-メチル-3-ブテニル基、1,1-ジメチル-2-プロペニル基、1-i-プロピルエテニル基、1,2-ジメチル-1-プロペニル基、1,2-ジメチル-2-プロペニル基、1-シクロペンテニル基、2-シクロペンテニル基、3-シクロペンテニル基、1-ヘキセニル基、2-ヘキセニル基、3-ヘキセニル基、4-ヘキセニル基、5-ヘキセニル基、1-メチル-1-ペンテニル基、1-メチル-2-ペンテニル基、1-メチル-3-ペンテニル基、1-メチル-4-ペンテニル基、1-n-ブチルエテニル基、2-メチル-1-ペンテニル基、2-メチル-2-ペンテニル基、2-メチル-3-ペンテニル基、2-メチル-4-ペンテニル基、2-n-プロピル-2-プロペニル基、3-メチル-1-ペンテニル基、3-メチル-2-ペンテニル基、3-メチル-3-ペンテニル基、3-メチル-4-ペンテニル基、3-エチル-3-ブテニル基、4-メチル-1-ペンテニル基、4-メチル-2-ペンテニル基、4-メチル-3-ペンテニル基、4-メチル-4-ペンテニル基、1,1-ジメチル-2-ブテニル基、1,1-ジメチル-3-ブテニル基、1,2-ジメチル-1-ブテニル基、1,2-ジメチル-2-ブテニル基、1,2-ジメチル-3-ブテニル基、1-メチル-2-エチル-2-プロペニル基、1-s-ブチルエテニル基、1,3-ジメチル-1-ブテニル基、1,3-ジメチル-2-ブテニル基、1,3-ジメチル-3-ブテニル基、1-i-ブチルエテニル基、2,2-ジメチル-3-ブテニル基、2,3-ジメチル-1-ブテニル基、2,3-ジメチル-2-ブテニル基、2,3-ジメチル-3-ブテニル基、2-i-プロピル-2-プロペニル基、3,3-ジメチル-1-ブテニル基、1-エチル-1-ブテニル基、1-エチル-2-ブテニル基、1-エチル-3-ブテニル基、1-n-プロピル-1-プロペニル基、1-n-プロピル-2-プロペニル基、2-エチル-1-ブテニル基、2-エチル-2-ブテニル基、2-エチル-3-ブテニル基、1,1,2-トリメチル-2-プロペニル基、1-t-ブチルエテニル基、1-メチル-1-エチル-2-プロペニル基、1-エチル-2-メチル-1-プロペニル基、1-エチル-2-メチル-2-プロペニル基、1-i-プロピル-1-プロペニル基、1-i-プロピル-2-プロペニル基、1-メチル-2-シクロペンテニル基、1-メチル-3-シクロペンテニル基、2-メチル-1-シクロペンテニル基、2-メチル-2-シクロペンテニル基、2-メチル-3-シクロペンテニル基、2-メチル-4-シクロペンテニル基、2-メチル-5-シクロペンテニル基、2-メチレン-シクロペンチル基、3-メチル-1-シクロペンテニル基、3-メチル-2-シクロペンテニル基、3-メチル-3-シクロペンテニル基、3-メチル-4-シクロペンテニル基、3-メチル-5-シクロペンテニル基、3-メチレン-シクロペンチル基、1-シクロヘキセニル基、2-シクロヘキセニル基及び3-シクロヘキセニル基等が挙げられ、またビシクロへプテニル基(ノルボルニル基)等の架橋環式のアルケニル基も挙げることができる。
また置換基において挙げたアリールオキシ基は、アリール基が酸素原子(-O-)を介して結合する基であり、このようなアリール基の具体例としては前述したものと同じものが挙げられる。アリールオキシ基の炭素数は、特に限定されるものではないが、好ましくは40以下、より好ましくは30以下、より一層好ましくは20以下であり、その具体例としては、フェノキシ基、ナフタレン-2-イルオキシ基等が挙げられるが、これらに限定されない。
また、置換基が2以上存在する場合、置換基同士が結合して環を形成してもよい。
アクリロイル基を有する有機基としては、アクリロイルメチル基、アクリロイルエチル基、アクリロイルプロピル基等が挙げられる。
メタクリロイル基を有する有機基としては、メタクリロイルメチル基、メタクリロイルエチル基、メタクリロイルプロピル基等が挙げられる。
メルカプト基を有する有機基としては、メルカプトエチル基、メルカプトブチル基、メルカプトヘキシル基、メルカプトオクチル基、メルカプトフェニル基等が挙げられる。
アミノ基を有する有機基としては、アミノ基、アミノメチル基、アミノエチル基、アミノフェニル基、ジメチルアミノエチル基、ジメチルアミノプロピル基等が挙げられるがこれらに限定されない。アミノ基を有する有機基については、更に詳細について後述する。
アルコキシ基を有する有機基としては、例えばメトキシメチル基、メトキシエチル基が挙げられるがこれらに限定されない。ただし、アルコキシ基が直接ケイ素原子に結合する基は除かれる。
スルホニル基を有する有機基としては、例えばスルホニルアルキル基や、スルホニルアリール基が挙げられるがこれらに限定されない。
シアノ基を有する有機基としては、シアノエチル基、シアノプロピル基、シアノフェニル基、チオシアネート基等が挙げられる。
炭化水素基としては、アルキル基、アルケニル基、アリール基等が挙げられるが、これらに限定されない。これらアルキル基、アルケニル基及びアリール基の具体例としては、R1において前述したものと同じものが挙げられる。
またアルキレン基としては、直鎖状でも分岐鎖状でもいずれでもよく、その炭素数は、通常1~10、好ましくは1~5である。例えば、メチレン基、エチレン基、トリメチレン基、テトラメチレン基、ペンタメチレン基、ヘキサメチレン基、ヘプタメチレン基、オクタメチレン基、ノナメチレン基、デカメチレン基等の直鎖状アルキレン基が挙げられる。
アミノ基を有する有機基としては、アミノ基、アミノメチル基、アミノエチル基、アミノフェニル基、ジメチルアミノエチル基、ジメチルアミノプロピル基等が挙げられるがこれらに限定されない。
R2におけるアルコキシ基としては、例えば、R1の説明で例示したアルコキシ基が挙げられる。
R2におけるハロゲン原子としては、例えば、R1の説明で例示したハロゲン原子が挙げられる。
アラルキルオキシ基の炭素数は特に限定されるものではないが、例えば40以下、好ましくは30以下、より好ましくは20以下とすることができる。
アラルキルオキシ基の具体例としては、フェニルメチルオキシ基(ベンジルオキシ基)、2-フェニルエチレンオキシ基、3-フェニル-n-プロピルオキシ基、4-フェニル-n-ブチルオキシ基、5-フェニル-n-ペンチルオキシ基、6-フェニル-n-ヘキシルオキシ基、7-フェニル-n-ヘプチルオキシ基、8-フェニル-n-オクチルオキシ基、9-フェニル-n-ノニルオキシ基、10-フェニル-n-デシルオキシ基等が挙げられるが、これらに限定されない。
アシルオキシ基の具体例としては、炭素数2~20のアシルオキシ基が挙げられ、例えばメチルカルボニルオキシ基、エチルカルボニルオキシ基、n-プロピルカルボニルオキシ基、i-プロピルカルボニルオキシ基、n-ブチルカルボニルオキシ基、i-ブチルカルボニルオキシ基、s-ブチルカルボニルオキシ基、t-ブチルカルボニルオキシ基、n-ペンチルカルボニルオキシ基、1-メチル-n-ブチルカルボニルオキシ基、2-メチル-n-ブチルカルボニルオキシ基、3-メチル-n-ブチルカルボニルオキシ基、1,1-ジメチル-n-プロピルカルボニルオキシ基、1,2-ジメチル-n-プロピルカルボニルオキシ基、2,2-ジメチル-n-プロピルカルボニルオキシ基、1-エチル-n-プロピルカルボニルオキシ基、n-ヘキシルカルボニルオキシ基、1-メチル-n-ペンチルカルボニルオキシ基、2-メチル-n-ペンチルカルボニルオキシ基、3-メチル-n-ペンチルカルボニルオキシ基、4-メチル-n-ペンチルカルボニルオキシ基、1,1-ジメチル-n-ブチルカルボニルオキシ基、1,2-ジメチル-n-ブチルカルボニルオキシ基、1,3-ジメチル-n-ブチルカルボニルオキシ基、2,2-ジメチル-n-ブチルカルボニルオキシ基、2,3-ジメチル-n-ブチルカルボニルオキシ基、3,3-ジメチル-n-ブチルカルボニルオキシ基、1-エチル-n-ブチルカルボニルオキシ基、2-エチル-n-ブチルカルボニルオキシ基、1,1,2-トリメチル-n-プロピルカルボニルオキシ基、1,2,2-トリメチル-n-プロピルカルボニルオキシ基、1-エチル-1-メチル-n-プロピルカルボニルオキシ基、1-エチル-2-メチル-n-プロピルカルボニルオキシ基、フェニルカルボニルオキシ基、及びトシルカルボニルオキシ基等が挙げられる。
式(1)で表される加水分解性シランの具体例としては、テトラメトキシシラン、テトラクロロシラン、テトラアセトキシシラン、テトラエトキシシラン、テトラ-n-プロポキシシラン、テトラ-i-プロポキシシラン、テトラ-n-ブトキシシラン、メチルトリメトキシシラン、メチルトリクロロシラン、メチルトリアセトキシシラン、メチルトリエトキシシラン、メチルトリプロポキシシラン、メチルトリブトキシシラン、メチルトリアミロキシシラン、メチルトリフェノキシシラン、メチルトリベンジルオキシシラン、メチルトリフェネチルオキシシラン、グリシドキシメチルトリメトキシシラン、グリシドキシメチルトリエトキシシラン、α-グリシドキシエチルトリメトキシシラン、α-グリシドキシエチルトリエトキシシラン、β-グリシドキシエチルトリメトキシシラン、β-グリシドキシエチルトリエトキシシラン、α-グリシドキシプロピルトリメトキシシラン、α-グリシドキシプロピルトリエトキシシラン、β-グリシドキシプロピルトリメトキシシラン、β-グリシドキシプロピルトリエトキシシラン、γ-グリシドキシプロピルトリメトキシシラン、γ-グリシドキシプロピルトリエトキシシラン、γ-グリシドキシプロピルトリプロポキシシラン、γ-グリシドキシプロピルトリブトキシシラン、γ-グリシドキシプロピルトリフェノキシシラン、α-グリシドキシブチルトリメトキシシラン、α-グリシドキシブチルトリエトキシシラン、β-グリシドキシブチルトリエトキシシラン、γ-グリシドキシブチルトリメトキシシラン、γ-グリシドキシブチルトリエトキシシラン、δ-グリシドキシブチルトリメトキシシラン、δ-グリシドキシブチルトリエトキシシラン、(3,4-エポキシシクロヘキシル)メチルトリメトキシシラン、(3,4-エポキシシクロヘキシル)メチルトリエトキシシラン、β-(3,4-エポキシシクロヘキシル)エチルトリメトキシシラン、β-(3,4-エポキシシクロヘキシル)エチルトリエトキシシラン、β-(3,4-エポキシシクロヘキシル)エチルトリプロポキシシラン、β-(3,4-エポキシシクロヘキシル)エチルトリブトキシシラン、β-(3,4-エポキシシクロヘキシル)エチルトリフェノキシシラン、γ-(3,4-エポキシシクロヘキシル)プロピルトリメトキシシラン、γ-(3,4-エポキシシクロヘキシル)プロピルトリエトキシシラン、δ-(3,4-エポキシシクロヘキシル)ブチルトリメトキシシラン、δ-(3,4-エポキシシクロヘキシル)ブチルトリエトキシシラン、グリシドキシメチルメチルジメトキシシラン、グリシドキシメチルメチルジエトキシシラン、α-グリシドキシエチルメチルジメトキシシラン、α-グリシドキシエチルメチルジエトキシシラン、β-グリシドキシエチルメチルジメトキシシラン、β-グリシドキシエチルエチルジメトキシシラン、α-グリシドキシプロピルメチルジメトキシシラン、α-グリシドキシプロピルメチルジエトキシシラン、β-グリシドキシプロピルメチルジメトキシシラン、β-グリシドキシプロピルエチルジメトキシシラン、γ-グリシドキシプロピルメチルジメトキシシラン、γ-グリシドキシプロピルメチルジエトキシシラン、γ-グリシドキシプロピルメチルジプロポキシシラン、γ-グリシドキシプロピルメチルジブトキシシラン、γ-グリシドキシプロピルメチルジフェノキシシラン、γ-グリシドキシプロピルエチルジメトキシシラン、γ-グリシドキシプロピルエチルジエトキシシラン、γ-グリシドキシプロピルビニルジメトキシシラン、γ-グリシドキシプロピルビニルジエトキシシラン、エチルトリメトキシシラン、エチルトリエトキシシラン、ビニルトリメトキシシラン、ビニルトリエトキシシラン、ビニルトリクロロシラン、ビニルトリアセトキシシラン、メチルビニルジメトキシシラン、メチルビニルジエトキシシラン、メチルビニルジクロロシラン、メチルビニルジアセトキシシラン、ジメチルビニルメトキシシラン、ジメチルビニルエトキシシラン、ジメチルビニルクロロシラン、ジメチルビニルアセトキシシラン、ジビニルジメトキシシラン、ジビニルジエトキシシラン、ジビニルジクロロシラン、ジビニルジアセトキシシラン、γ-グリシドキシプロピルビニルジメトキシシラン、γ-グリシドキシプロピルビニルジエトキシシラン、アリルトリメトキシシラン、アリルトリエトキシシラン、アリルトリクロロシラン、アリルトリアセトキシシシラン、アリルメチルジメトキシシラン、アリルメチルジエトキシシラン、アリルメチルジクロロシラン、アリルメチルジアセトキシシラン、アリルジメチルメトキシシラン、アリルジメチルエトキシシラン、アリルジメチルクロロシラン、アリルジメチルアセトキシシラン、ジアリルジメトキシシラン、ジアリルジエトキシシラン、ジアリルジクロロシラン、ジアリルジアセトキシシラン、3-アリルアミノプロピルトリメトキシシラン、3-アリルアミノプロピルトリエトキシシラン、p-スチリルトリメトキシシラン、フェニルトリメトキシシラン、フェニルトリエトキシシラン、フェニルトリクロロシラン、フェニルトリアセトキシシラン、フェニルメチルジメトキシシラン、フェニルメチルジエトキシシラン、フェニルメチルジクロロシラン、フェニルメチルジアセトキシシラン、フェニルジメチルメトキシシラン、フェニルジメチルエトキシシラン、フェニルジメチルクロロシラン、フェニルジメチルアセトキシシラン、ジフェニルメチルメトキシシラン、ジフェニルメチルエトキシシラン、ジフェニルメチルクロロシラン、ジフェニルメチルアセトキシシラン、ジフェニルジメトキシシラン、ジフェニルジエトキシシラン、ジフェニルジクロロシラン、ジフェニルジアセトキシシラン、トリフェニルメトキシシシラン、トリフェニルエトキシシラン、トリフェニルアセトキシシラン、トリフェニルクロロシラン、3-フェニルアミノプロピルトリメトキシシラン、3-フェニルアミノプロピルトリエトキシシラン、ジメトキシメチル-3-(3-フェノキシプロピルチオプロピル)シラン、トリエトキシ((2-メトキシ-4-(メトキシメチル)フェノキシ)メチル)シラン、ベンジルトリメトキシシラン、ベンジルトリエトキシシラン、ベンジルメチルジメトキシシラン、ベンジルメチルジエトキシシラン、ベンジルジメチルメトキシシラン、ベンジルジメチルエトキシシラン、ベンジルジメチルクロロシラン、フェネチルトリメトキシシラン、フェネチルトリエトキシシラン、フェネチルトリクロロシラン、フェネチルトリアセトキシシラン、フェネチルメチルジメトキシシラン、フェネチルメチルジエトキシシラン、フェネチルメチルジクロロシラン、フェネチルメチルジアセトキシシラン、メトキシフェニルトリメトキシシラン、メトキシフェニルトリエトキシシラン、メトキシフェニルトリアセトキシシラン、メトキシフェニルトリクロロシラン、メトキシベンジルトリメトキシシラン、メトキシベンジルトリエトキシシラン、メトキシベンジルトリアセトキシシラン、メトキシベンジルトリクロロシラン、メトキシフェネチルトリメトキシシラン、メトキシフェネチルトリエトキシシラン、メトキシフェネチルトリアセトキシシラン、メトキシフェネチルトリクロロシラン、エトキシフェニルトリメトキシシラン、エトキシフェニルトリエトキシシラン、エトキシフェニルトリアセトキシシラン、エトキシフェニルトリクロロシラン、エトキシベンジルトリメトキシシラン、エトキシベンジルトリエトキシシラン、エトキシベンジルトリアセトキシシラン、エトキシベンジルトリクロロシラン、i-プロポキシフェニルトリメトキシシラン、i-プロポキシフェニルトリエトキシシラン、i-プロポキシフェニルトリアセトキシシラン、i-プロポキシフェニルトリクロロシラン、i-プロポキシベンジルトリメトキシシラン、i-プロポキシベンジルトリエトキシシラン、i-プロポキシベンジルトリアセトキシシラン、i-プロポキシベンジルトリクロロシラン、t-ブトキシフェニルトリメトキシシラン、t-ブトキシフェニルトリエトキシシラン、t-ブトキシフェニルトリアセトキシシラン、t-ブトキシフェニルトリクロロシラン、t-ブトキシベンジルトリメトキシシラン、t-ブトキシベンジルトリエトキシシラン、t-ブトキシベンジルトリアセトキシシラン、t-ブトキシシベンジルトリクロロシラン、メトキシナフチルトリメトキシシラン、メトキシナフチルトリエトキシシラン、メトキシナフチルトリアセトキシシラン、メトキシナフチルトリクロロシラン、エトキシナフチルトリメトキシシラン、エトキシナフチルトリエトキシシラン、エトキシナフチルトリアセトキシシラン、エトキシナフチルトリクロロシラン、γ-クロロプロピルトリメトキシシラン、γ-クロロプロピルトリエトキシシラン、γ-クロロプロピルトリアセトキシシラン、3,3,3-トリフルオロプロピルトリメトキシシラン、γ-メタクリルオキシプロピルトリメトキシシラン、γ-メルカプトプロピルトリメトキシシラン、γ-メルカプトプロピルトリエトキシシラン、β-シアノエチルトリエトキシシラン、チオシアネートプロピルトリエトキシシラン、クロロメチルトリメトキシシラン、クロロメチルトリエトキシシラン、トリエトキシシリルプロピルジアリルイソシアヌレート、ビシクロ[2,2,1]ヘプテニルトリエトキシシラン、ベンゼンスルホニルプロピルトリエトキシシラン、ベンゼンスルホンアミドプロピルトリエトキシシラン、ジメチルアミノプロピルトリメトキシシラン、ジメチルジメトキシシラン、フェニルメチルジメトキシシラン、ジメチルジエトキシシラン、フェニルメチルジエトキシシラン、γ-クロロプロピルメチルジメトキシシラン、γ-クロロプロピルメチルジエトキシシラン、ジメチルジアセトキシシラン、γ-メタクリルオキシプロピルメチルジメトキシシラン、γ-メタクリルオキシプロピルメチルジエトキシシラン、γ-メルカプトプロピルメチルジメトキシシラン、γ-メルカプトメチルジエトキシシラン、メチルビニルジメトキシシラン、メチルビニルジエトキシシランや、下記式(A-1)~(A-41)で表されるシラン、下記式(1-1)~(1-290)で表されるシラン等が挙げられるが、これらに限定されない。
またR4は、ケイ素原子に結合する基又は原子であって、互いに独立して、アルコキシ基、アラルキルオキシ基、アシルオキシ基、又はハロゲン原子を表す。
R5は、ケイ素原子に結合する基であって、互いに独立して、アルキレン基又はアリーレン基を表す。
bは、0又は1を表し、cは、0又は1を表す。
R4における各基及び原子の具体例、及びそれらの好適な炭素数としては、R2について前述した基及び原子並びに炭素数を挙げることができる。
R5におけるアルキレン基の具体例としては、メチレン基、エチレン基、トリメチレン基、テトラメチレン基、ペンタメチレン基、ヘキサメチレン基、ヘプタメチレン基、オクタメチレン基、ノナメチレン基、デカメチレン基等の直鎖状アルキレン基、1-メチルトリメチレン基、2-メチルトリメチレン基、1,1-ジメチルエチレン基、1-メチルテトラメチレン基、2-メチルテトラメチレン基、1,1-ジメチルトリメチレン基、1,2-ジメチルトリメチレン基、2,2-ジメチルトリメチレン基、1-エチルトリメチレン基等の分岐鎖状アルキレン基等のアルキレン基、メタントリイル基、エタン-1,1,2-トリイル基、エタン-1,2,2-トリイル基、エタン-2,2,2-トリイル基、プロパン-1,1,1-トリイル基、プロパン-1,1,2-トリイル基、プロパン-1,2,3-トリイル基、プロパン-1,2,2-トリイル基、プロパン-1,1,3-トリイル基、ブタン-1,1,1-トリイル基、ブタン-1,1,2-トリイル基、ブタン-1,1,3-トリイル基、ブタン-1,2,3-トリイル基、ブタン-1,2,4-トリイル基、ブタン-1,2,2-トリイル基、ブタン-2,2,3-トリイル基、2-メチルプロパン-1,1,1-トリイル基、2-メチルプロパン-1,1,2-トリイル基、2-メチルプロパン-1,1,3-トリイル基のアルカントリイル基等が挙げられるが、これらに限定されない。
R5におけるアリーレン基の具体例としては、1,2-フェニレン基、1,3-フェニレン基、1,4-フェニレン基;1,5-ナフタレンジイル基、1,8-ナフタレンジイル基、2,6-ナフタレンジイル基、2,7-ナフタレンジイル基、1,2-アントラセンジイル基、1,3-アントラセンジイル基、1,4-アントラセンジイル基、1,5-アントラセンジイル基、1,6-アントラセンジイル基、1,7-アントラセンジイル基、1,8-アントラセンジイル基、2,3-アントラセンジイル基、2,6-アントラセンジイル基、2,7-アントラセンジイル基、2,9-アントラセンジイル基、2,10-アントラセンジイル基、9,10-アントラセンジイル基等の縮合環芳香族炭化水素化合物の芳香環上の水素原子を二つ取り除いて誘導される基;4,4’-ビフェニルジイル基、4,4’’-パラテルフェニルジイル基の環連結芳香族炭化水素化合物の芳香環上の水素原子を二つ取り除いて誘導される基等が挙げられるが、これらに限定されない。
bは、好ましく0である。
cは、好ましくは1である。
その他の加水分解性シランとして、オニウム基を分子内に有するシラン化合物、スルホン基を有するシラン化合物、スルホンアミド基を有するシラン化合物、環状尿素骨格を分子内に有するシラン化合物等が挙げられるが、これらに限定されない。
オニウム基を分子内に有するシラン化合物は、加水分解性シランの架橋反応を効果的に且つ効率的に促進できることが期待される。
R12は、ケイ素原子に結合する基であって、互いに独立して、置換されていてもよいアルキル基、置換されていてもよいアリール基、置換されていてもよいアラルキル基、置換されていてもよいハロゲン化アルキル基、置換されていてもよいハロゲン化アリール基、置換されていてもよいハロゲン化アラルキル基、置換されていてもよいアルコキシアルキル基、置換されていてもよいアルコキシアリール基、置換されていてもよいアルコキシアラルキル基、若しくは置換されていてもよいアルケニル基を表すか、又はエポキシ基を有する有機基、アクリロイル基を有する有機基、メタクリロイル基を有する有機基、メルカプト基を有する有機基、アミノ基を有する有機基、若しくはシアノ基を有する有機基、又はそれらの2種以上の組み合わせを表す。
R13は、ケイ素原子に結合する基又は原子であって、互いに独立して、アルコキシ基、アラルキルオキシ基、アシルオキシ基、又はハロゲン原子を表す。
fは1又は2を表し、gは0又は1を表し、1≦f+g≦2を満たす。
すなわち、オニウム基又はそれを有する有機基の好適な具体例としては、環状アンモニウム基若しくは鎖状アンモニウム基又はこれらの少なくとも一方を有する有機基が挙げられ、第3級アンモニウム基若しくは第4級アンモニウム基又はこれらの少なくとも一方を有する有機基が好ましい。
なお、オニウム基が環状アンモニウム基である場合、アンモニウム基を構成する窒素原子が環を構成する原子を兼ねる。この際、環を構成する窒素原子とシリコン原子とが直接又は2価の連結基を介して結合している場合と、環を構成する炭素原子とシリコン原子が直接に又は2価の連結基を介して結合している場合とがある。
このようなアルキル基、アリール基、アラルキル基、ハロゲン化アルキル基、ハロゲン化アリール基、ハロゲン化アラルキル基及びアルケニル基の具体例及びそれらの好適な炭素数としては、前述と同じものが挙げられる。
m1が0である場合、A1~A4を含む(4+n1)員環が構成される。すなわち、n1が1であるときは5員環、n1が2であるときは6員環、n1が3であるときは7員環、n1が4であるときは8員環、n1が5であるときは9員環、n1が6であるときは10員環、n1が7であるときは11員環、n1が8であるときは12員環が、それぞれ構成される。
m1が1である場合、A1~A3を含む(4+n1)員環とA4を含む6員環とが縮合した縮合環が形成される。
A1~A4は、式(J1)~式(J3)のいずれであるか次第で、環を構成する原子上に水素原子を有する場合と、水素原子を有さない場合があるが、A1~A4が、環を構成する原子上に水素原子を有する場合、その水素原子は、R14に置き換わっていてもよい。また、A1~A4中の環構成原子以外の環構成原子に、R14が置換していてもよい。このような事情から、前述の通り、m2は、0又は1から単環若しくは多環に置換可能な最大数までの整数から選択される。
このような連結基としては、アルキレン基、アリーレン基、アルケニレン基等が挙げられるが、これらに限定されない。
アルキレン基及びアリーレン基の具体例及びそれらの好適な炭素数としては、前述したものと同じものが挙げられる。
その具体例としては、ビニレン、1-メチルビニレン、プロペニレン、1-ブテニレン、2-ブテニレン、1-ペンテニレン、2-ペンテニレン基等が挙げられるが、これらに限定されない。
アルキル基、アリール基、アラルキル基、ハロゲン化アルキル基、ハロゲン化アリール基、ハロゲン化アラルキル基及びアルケニル基の具体例及びそれらの好適な炭素数としては、前述したものと同じものが挙げられる。
m3が0である場合、A5~A8を含む(4+n2)員環が構成される。すなわち、n2が1であるときは5員環、n2が2であるときは6員環、n2が3であるときは7員環、n2が4であるときは8員環、n2が5であるときは9員環、n2が6であるときは10員環、n2が7であるときは11員環、n2が8であるときは12員環が、それぞれ構成される。
m3が1である場合、A5~A7を含む(4+n2)員環とA8を含む6員環とが縮合した縮合環が形成される。
A5~A8は、式(J4)~式(J6)のいずれであるか次第で、環を構成する原子上に水素原子を有する場合と、水素原子を有さない場合があるが、A5~A8が、環を構成する原子上に水素原子を有する場合、その水素原子は、R15に置き換わっていてもよい。また、A5~A8中の環構成原子以外の環構成原子に、R15が置換していてもよい。
このような事情から、前述の通り、m4は、0又は1から単環若しくは多環に置換可能な最大数までの整数から選択される。
このような連結基としては、アルキレン基、アリーレン基又はアルケニレン基が挙げられ、アルキレン基、アリーレン基及びアルケニレン基の具体例及びそれらの好適な炭素数としては、前述と同じものが挙げられる。
このような連結基としては、アルキレン基、アリーレン基又はアルケニレン基が挙げられ、アルキレン基、アリーレン基及びアルケニレン基の具体例としては、前述と同じものが挙げられる。
スルホン基を有するシラン化合物、及びスルホンアミド基を有するシラン化合物としては、例えば下記式(B-1)~式(B-36)で表される化合物が挙げられるが、これらに限定されない。
下記式中、Meはメチル基を、Etはエチル基をそれぞれ表す。
環状尿素骨格を分子内に有する加水分解性オルガノシランとして、例えば下記式(4-1)で表される加水分解性オルガノシランが挙げられる。
R402は、ケイ素原子に結合する基であり、置換されていてもよいアルキル基、置換されていてもよいアリール基、置換されていてもよいアラルキル基、置換されていてもよいハロゲン化アルキル基、置換されていてもよいハロゲン化アリール基、置換されていてもよいハロゲン化アラルキル基、置換されていてもよいアルコキシアルキル基、置換されていてもよいアルコキシアリール基、置換されていてもよいアルコキシアラルキル基、若しくは置換されていてもよいアルケニル基を表すか、又はエポキシ基を有する有機基、アクリロイル基を有する有機基、メタクリロイル基を有する有機基、メルカプト基を有する有機基若しくはシアノ基を有する有機基、又はそれらの2種以上の組み合わせを表す。
R403は、ケイ素原子に結合する基又は原子であり、互いに独立して、アルコキシ基、アラルキルオキシ基、アシルオキシ基又はハロゲン原子を表す。
xは、1又は2であり、yは、0又は1であり、x+y≦2を満たす。
R402のアルキル基、アリール基、アラルキル基、ハロゲン化アルキル基、ハロゲン化アリール基、ハロゲン化アラルキル基、アルコキシアルキル基、アルコキシアリール基、アルコキシアラルキル基、アルケニル基、及び、エポキシ基を有する有機基、アクリロイル基を有する有機基、メタクリロイル基を有する有機基、メルカプト基を有する有機基及びシアノ基を有する有機基、並びに、R403のアルコキシ基、アラルキルオキシ基、アシルオキシ基及びハロゲン原子、並びにこれらの置換基の具体例、好適な炭素数等は、R1及びR2に関し前述したものと同じものが挙げられる。
なお、R404の置換されていてもよいアルキル基、置換されていてもよいアルケニル基及びエポキシ基を有する有機基の具体例及び好適な炭素数等は、R1に関し前述したものと同じものが挙げられるが、これらの他、R404の置換されていてもよいアルキル基としては、末端の水素原子がビニル基で置換されたアルキル基が好ましく、その具体例としては、アリル基、2-ビニルエチル基、3-ビニルプロピル基、4-ビニルブチル基等が挙げられる。
これらの基におけるアルキル基、アリール基、アラルキル基、ハロゲン化アルキル基、ハロゲン化アリール基、ハロゲン化アラルキル基、アルコキシアルキル基、アルコキシアリール基、アルコキシアラルキル基、及びアルケニル基、並びにそれらの置換基の具体例及び好適な炭素数等は、R1に関し前述したものと同じものが挙げられる。
アルキレン基の具体例としては、メチレン基、エチレン基、トリメチレン基、テトラメチレン基、ペンタメチレン基、ヘキサメチレン基、ヘプタメチレン基、オクタメチレン基、ノナメチレン基、デカメチレン基等の直鎖状アルキレン基、メチルエチレン基、1-メチルトリメチレン基、2-メチルトリメチレン基、1,1-ジメチルエチレン基、1-メチルテトラメチレン基、2-メチルテトラメチレン基、1,1-ジメチルトリメチレン基、1,2-ジメチルトリメチレン基、2,2-ジメチルトリメチレン基、1-エチルトリメチレン基等の分岐鎖状アルキレン基、1,2-シクロプロパンジイル基、1,2-シクロブタンジイル基、1,3-シクロブチタンジイル基、1,2-シクロヘキサンジイル、1,3-シクロヘキサンジイル基等の環状アルキレン等、-CH2OCH2-、-CH2CH2OCH2-、-CH2CH2OCH2CH2-、-CH2CH2CH2OCH2CH2-、-CH2CH2OCH2CH2CH2-、-CH2CH2CH2OCH2CH2CH2-、-CH2SCH2-、-CH2CH2SCH2-、-CH2CH2SCH2CH2-、-CH2CH2CH2SCH2CH2-、-CH2CH2SCH2CH2CH2-、-CH2CH2CH2SCH2CH2CH2-、-CH2OCH2CH2SCH2-等のエーテル基等を含むアルキレン基が挙げられるが、これらに限定されない。
中でも、優れたリソグラフィー特性を再現性よく実現する観点から、X401は式(4-5)で表される基が好ましい。
該変性物であるポリシロキサンは、前述の加水分解性シランの加水分解縮合物において、該縮合物が有するシラノール基の少なくとも一部とアルコールのヒドロキシ基との反応により得られる反応生成物、該縮合物とアルコールとの脱水反応物、また、該縮合物が有するシラノール基の少なくとも一部をアセタール基で保護した変性物等を挙げることができる。
また例えば3-メトキシブタノール、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、プロピレングリコールモノメチルエーテル(1-メトキシ-2-プロパノール)、プロピレングリコールモノエチルエーテル(1-エトキシ-2-プロパノール)、プロピレングリコールモノブチルエーテル(1-ブトキシ-2-プロパノール)等のアルコキシ基含有アルコールを用いることができる。
酸は、酸解離定数(pka)が-1~5、好ましくは4~5である有機酸を用いることができる。例えば、酸は、トリフルオロ酢酸、マレイン酸、安息香酸、イソ酪酸、酢酸等、中でも安息香酸、イソ酪酸、酢酸等を例示することができる。
また、酸は、70~160℃の沸点を有する酸を用いることができ、例えば、トリフルオロ酢酸、イソ酪酸、酢酸、硝酸等が挙げられる。
このように酸としては、酸解離定数(pka)が4~5であるか、又は沸点が70~160℃であるか、いずれかの物性を有するものが好ましい。即ち、酸性度が弱いものか、又は酸性度は強くても沸点が低いものを用いることができる。
そして、酸としては酸解離定数、沸点の性質からいずれの性質を利用することも可能である。
好ましい一態様において、[A]ポリシロキサンは、加水分解縮合物とアルコールとの脱水反応物を含む。
なお、重量平均分子量は、GPC分析によるポリスチレン換算にて得られる分子量である。GPC分析は、例えばGPC装置(商品名HLC-8220GPC、東ソー株式会社製)、GPCカラム(商品名Shodex(登録商標)KF803L、KF802、KF801、昭和電工株式会社製)、カラム温度を40℃とし、溶離液(溶出溶媒)としてテトラヒドロフランを用い、流量(流速)は1.0mL/minとし、標準試料はポリスチレン(昭和電工株式会社製Shodex(登録商標))を用いて行うことができる。
前述のシラン化合物(加水分解性シラン)は、ケイ素原子に直接結合するアルコキシ基、アラルキルオキシ基、アシルオキシ基、又はハロゲン原子を、すなわちアルコキシシリル基、アラルキルオキシシリル基、アシロキシシリル基、又はハロゲン化シリル基(以下、加水分解性基と称する)を含む。
これら加水分解性基の加水分解には、加水分解性基の1モル当たり、通常0.1~100モル、例えば0.5~100モル、好ましくは1~10モルの水を用いる。
加水分解及び縮合の際、反応を促進する目的等で、加水分解触媒を用いてもよいし、用いずに加水分解及び縮合を行ってもよい。加水分解触媒を用いる場合は、加水分解性基の1モル当たり、通常0.0001~10モル、好ましくは0.001~1モルの加水分解触媒を用いることができる。
加水分解と縮合を行う際の反応温度は、通常、室温以上、加水分解に用いられ得る有機溶媒の常圧での還流温度以下の範囲であり、例えば20~110℃、また例えば20~80℃とすることができる。
加水分解は完全に加水分解を行う、すなわち、全ての加水分解性基をシラノール基に変えてもよいし、部分加水分解する、即ち未反応の加水分解基を残してもよい。
加水分解し縮合させる際に使用可能な加水分解触媒としては、金属キレート化合物、有機酸、無機酸、有機塩基、無機塩基を挙げることができる。
また、前述の通り、硝酸は、加水分解縮合物の変性物を得る際、例えばシラノール基のアルコールによるキャッピングの際にも使用し得るため、加水分解性シランの加水分解及び縮合と、加水分解縮合物のアルコールキャッピングの双方の反応に寄与できるものとなり得る観点からも好ましい。
得られたポリシロキサンワニスは溶媒置換してもよいし、また適宜溶媒で希釈してもよい。なお得られたポリシロキサンワニスは、その保存安定性が悪くなければ、有機溶媒を留去し、膜形成成分濃度100%とすることもできる。なお膜形成成分とは、組成物の全成分から溶媒成分を除いた成分を指す。
ポリシロキサンワニスの溶媒置換や希釈等に用いる有機溶媒は、加水分解性シランの加水分解及び縮合反応に用いた有機溶媒と同じでも異なってもよい。この希釈用溶媒は、特に限定されず、1種でも2種以上でも任意に選択して用いることができる。
[B]成分は、スルホン酸化合物と、pKa(酸解離定数)が-15.0~1.2の酸とから選ばれる少なくとも1種である。[B]成分は、例えば、硫酸(H2SO4)と、スルホン酸化合物とから選ばれる少なくとも1種である。
本発明におけるスルホン酸化合物は、スルホ基(-SO3H)を有する化合物である。
スルホン酸化合物がヒドロキシ基を有する場合、スルホン酸化合物におけるスルホ基(S)とヒドロキシ基(H)との個数割合(S:H)としては、特に制限されないが、例えば、3:1~1:3である。
スルホン酸化合物としては、25℃、1.01×105Paで、液体であっても、固体であってもよい。
スルホン酸化合物の分子量としては、特に制限されないが、加熱時の揮発を抑制する観点と組成物中での析出や不均一性を回避する観点等のバランスから、例えば、96~1,000である。
スルホン酸化合物におけるスルホ基(-SO3H;分子量81)の割合としては、特に制限されないが、スルホ基1mol当たりのスルホン酸化合物の質量として、好ましくは50~500である。
スルホン酸化合物の中にはpKaが-15.0~1.2のものもある。そのようなpKaが-15.0~1.2のスルホン酸化合物は、スルホン酸化合物であり、かつpKaが-15.0~1.2の酸でもある。
pKaが-15.0~1.2の酸としては、例えば、pKaが-15.0~1.2の酸の過ハロゲン酸、pKaが-15.0~1.2の酸のリン酸類、pKaが-15.0~1.2の酸のホウ酸類、pKaが-15.0~1.2の酸のスルホンイミド類などが挙げられる。
pKaが-15.0~1.2の過ハロゲン酸としては、例えば、過塩素酸、過ヨウ素酸などが挙げられる。
pKaが-15.0~1.2のリン酸類としては、例えば、ヘキサフルオロリン酸などが挙げられる。
pKaが-15.0~1.2のホウ酸類としては、テトラフルオロホウ酸などが挙げられる。
pKaが-15.0~1.2のスルホンイミド類としては、例えば、ビストリフルオロメタンスルホンイミド酸などが挙げられる。
[C]成分としての溶媒は、[A]成分、及び[B]成分、並びに必要に応じてシリコン含有レジスト下層膜形成用組成物に含有されるその他成分を溶解・混和できる溶媒であれば特に制限なく使用することができる。
アルキレングリコールモノアルキルエーテルとしては、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノプロピルエーテル、エチレングリコールモノブチルエーテル、プロピレングリコールモノメチルエーテル(1-メトキシ-2-プロパノール)、プロピレングリコールモノエチルエーテル(1-エトキシ-2-プロパノール)、メチルイソブチルカルビノール、プロピレングリコールモノブチルエーテル等が挙げられる。
シリコン含有レジスト下層膜形成用組成物は、硬化触媒を含有しない組成物とすることができるが、硬化触媒([D]成分)を含有することが好ましい。
シリコン含有レジスト下層膜形成用組成物が[B]成分と[D]成分との両方を含有することにより、[B]成分を含有することによる本発明の効果をより十分に得ることができる。
シリコン含有レジスト下層膜形成用成組成物は、好ましくは[E]硝酸を含有する。
[B]硝酸は、シリコン含有レジスト下層膜形成用組成物の調製時に添加してもよいが、前述のポリシロキサンの製造において、加水分解触媒としてやシラノール基のアルコールキャッピング時に使用し、これがポリシロキサンワニス中に残存したものを[E]硝酸として扱うこともできる。
シリコン含有レジスト下層膜形成用組成物は、本発明の効果をより十分に得る観点から、好ましくは[F]アミンと水酸化物とから選ばれる少なくとも1種を含有する。
無機アルカリ水酸化物としては、例えば、水酸化ナトリウム、水酸化カリウム等が挙げられる。
有機アルカリ水酸化物としては、例えば、テトラアルキルアンモニウム水酸化物、トリアリールスルホニウム水酸化物、ジアリールヨードニウム水酸化物等が挙げられる。テトラアルキルアンモニウム水酸化物としては、例えば、テトラメチルアンモニウム水酸化物、テトラエチルアンモニウム水酸化物、テトラブチルアンモニウム水酸化物等が挙げられる。トリアリールスルホニウム水酸化物としては、例えば、トリフェニルスルホニウム水酸化物、トリス(t-ブチルフェニル)スルホニウム水酸化物等が挙げられる。ジアリールヨードニウム水酸化物としては、ジフェニルヨードニウム水酸化物、ビス(t-ブチルフェニル)ヨードニウム水酸化物等が挙げられる。
シリコン含有レジスト下層膜形成用組成物には、組成物の用途に応じて種々の添加剤を配合可能である。
添加剤としては、例えば、架橋剤、架橋触媒、安定化剤(有機酸、水、アルコール等)、有機ポリマー、酸発生剤、界面活性剤(ノニオン系界面活性剤、アニオン系界面活性剤、カチオン系界面活性剤、シリコン系界面活性剤、フッ素系界面活性剤、UV硬化型界面活性剤等)、pH調整剤、金属酸化物、レオロジー調整剤、接着補助剤等、レジスト下層膜や、反射防止膜、パターン反転用膜など、半導体装置の製造に使用され得る各種膜を形成する材料(組成物)に配合される公知の添加剤を挙げることができる。
なお以下に各種添加剤を例示するが、これらに限定されるものではない。
安定化剤は、加水分解性シラン混合物の加水分解縮合物の安定化等の目的のために添加され得、その具体例として、有機酸、水、アルコール、又はそれらの組み合わせを添加することができる。
有機酸としては、例えばシュウ酸、マロン酸、メチルマロン酸、コハク酸、マレイン酸、リンゴ酸、酒石酸、フタル酸、クエン酸、グルタル酸、乳酸、サリチル酸等が挙げられる。中でも、シュウ酸、マレイン酸が好ましい。有機酸を添加する場合、その添加量は、加水分解性シラン混合物の加水分解縮合物の質量に対して、0.1~5.0質量%である。これら有機酸はpH調整剤としても働き得る。
水としては、純水、超純水、イオン交換水等を用いることができ、使用する場合、その添加量は、シリコン含有レジスト下層膜形成用組成物100質量部に対して1~20質量部とすることができる。
アルコールとしては塗布後の加熱により飛散しやすいものが好ましく、例えばメタノール、エタノール、プロパノール、i-プロパノール、ブタノール等が挙げられる。アルコールを添加する場合、その添加量は、シリコン含有レジスト下層膜形成用組成物100質量部に対して1~20質量部とすることができる。
有機ポリマーは、シリコン含有レジスト下層膜形成用組成物に添加することにより、組成物から形成される膜(レジスト下層膜)のドライエッチング速度(単位時間当たりの膜厚の減少量)や、また減衰係数や屈折率等を調整することができる。有機ポリマーとしては特に制限はなく、その添加目的に応じて、種々の有機ポリマー(縮重合ポリマー及び付加重合ポリマー)の中から適宜選択される。
その具体例としては、ポリエステル、ポリスチレン、ポリイミド、アクリルポリマー、メタクリルポリマー、ポリビニルエーテル、フェノールノボラック、ナフトールノボラック、ポリエーテル、ポリアミド、ポリカーボネート等の付加重合ポリマー及び縮重合ポリマーが挙げられる。
本発明においては、吸光部位として機能するベンゼン環、ナフタレン環、アントラセン環、トリアジン環、キノリン環、キノキサリン環等の芳香環や複素芳香環を含む有機ポリマーも、そのような機能が必要な場合には、好適に用い得る。そのような有機ポリマーの具体例としては、ベンジルアクリレート、ベンジルメタクリレート、フェニルアクリレート、ナフチルアクリレート、アントリルメタクリレート、アントリルメチルメタクリレート、スチレン、ヒドロキシスチレン、ベンジルビニルエーテル及びN-フェニルマレイミド等の付加重合性モノマーをその構造単位として含む付加重合ポリマーや、フェノールノボラック及びナフトールノボラック等の縮重合ポリマーが挙げられるが、これらに限定されない。
付加重合ポリマーの製造には付加重合性モノマーが使用されるが、そのような付加重合性モノマーの具体例としては、アクリル酸、メタクリル酸、アクリル酸エステル化合物、メタクリル酸エステル化合物、アクリルアミド化合物、メタクリルアミド化合物、ビニル化合物、スチレン化合物、マレイミド化合物、マレイン酸無水物、アクリロニトリル等が挙げられるが、これらに限定されない。
有機ポリマーがヒドロキシ基を含む場合は、このヒドロキシ基は、加水分解縮合物等と架橋反応をし得る。
このような有機ポリマーは、1種単独で使用してもよいし、2種以上組み合わせて用いることができる。
酸発生剤としては、熱酸発生剤や光酸発生剤が挙げられ、光酸発生剤を好ましく用いることができる。
光酸発生剤としては、オニウム塩化合物、スルホンイミド化合物、ジスルホニルジアゾメタン化合物等が挙げられるが、これらに限定されない。なお光酸発生剤は、例えば後述するオニウム塩化合物における硝酸塩やマレイン酸塩などのカルボン酸塩、また塩酸塩など、その種類によっては硬化触媒としても機能し得る。
また熱酸発生剤としては、例えばテトラメチルアンモニウム硝酸塩などが挙げられるが、これに限定されない。
なお酸発生剤は、1種単独で又は2種以上組み合わせて用いることができ、また、光酸発生剤と熱酸発生剤とを併用してもよい。
界面活性剤は、シリコン含有レジスト下層膜形成用組成物を基板に塗布した際に、ピンホール、ストレーション等の発生を抑制するのに有効である。界面活性剤としては、ノニオン系界面活性剤、アニオン系界面活性剤、カチオン系界面活性剤、シリコン系界面活性剤、フッ素系界面活性剤、UV硬化型界面活性剤等が挙げられる。より具体的には、例えば、ポリオキシエチレンラウリルエーテル、ポリオキシエチレンステアリルエーテル、ポリオキシエチレンセチルエーテル、ポリオキシエチレンオレイルエーテル等のポリオキシエチレンアルキルエーテル類、ポリオキシエチレンオクチルフェノールエーテル、ポリオキシエチレンノニルフェノールエーテル等のポリオキシエチレンアルキルアリールエーテル類、ポリオキシエチレン・ポリオキシプロピレンブロックコポリマー類、ソルビタンモノラウレート、ソルビタンモノパルミテート、ソルビタンモノステアレート、ソルビタンモノオレエート、ソルビタントリオレエート、ソルビタントリステアレート等のソルビタン脂肪酸エステル類、ポリオキシエチレンソルビタンモノラウレート、ポリオキシエチレンソルビタンモノパルミテート、ポリオキシエチレンソルビタンモノステアレート、ポリオキシエチレンソルビタントリオレエート、ポリオキシエチレンソルビタントリステアレート等のポリオキシエチレンソルビタン脂肪酸エステル類等のノニオン系界面活性剤、商品名エフトップ(登録商標)EF301、EF303、EF352(三菱マテリアル電子化成(株)(旧(株)トーケムプロダクツ)製)、商品名メガファック(登録商標)F171、F173、R-08、R-30、R-30N、R-40LM(DIC(株)製)、フロラードFC430、FC431(スリーエムジャパン(株)製)、商品名アサヒガード(登録商標)AG710(AGC(株)製)、サーフロン(登録商標)S-382、SC101、SC102、SC103、SC104、SC105、SC106(AGCセイミケミカル(株)製)等のフッ素系界面活性剤、及びオルガノシロキサンポリマ-KP341(信越化学工業(株)製)等を挙げることができるが、これらに限定されない。
界面活性剤は、1種単独で又は2種以上組み合わせて用いることができる。
レオロジー調整剤は、主にシリコン含有レジスト下層膜形成用組成物の流動性を向上させ、特にベーキング工程において、形成される膜の膜厚均一性の向上や、ホール内部への組成物の充填性を高める目的で添加される。具体例としては、ジメチルフタレート、ジエチルフタレート、ジi-ブチルフタレート、ジヘキシルフタレート、ブチルi-デシルフタレート等のフタル酸誘導体、ジノルマルブチルアジペート、ジ-i-ブチルアジペート、ジ-i-オクチルアジペート、オクチルデシルアジペート等のアジピン酸誘導体、ジノルマルブチルマレート、ジエチルマレート、ジノニルマレート等のマレイン酸誘導体、メチルオレート、ブチルオレート、テトラヒドロフルフリルオレート等のオレイン酸誘導体、またはノルマルブチルステアレート、グリセリルステアレート等のステアリン酸誘導体等を挙げることができる。
これらのレオロジー調整剤が使用される場合、その添加量は、シリコン含有レジスト下層膜形成用組成物の全膜形成成分に対して通常30質量%未満である。
接着補助剤は、主に基板あるいはレジストと、シリコン含有レジスト下層膜形成用組成物から形成される膜(レジスト下層膜)との密着性を向上させ、特に現像においてレジストの剥離を抑制・防止する目的で添加される。具体例としては、トリメチルクロロシラン、ジメチルビニルクロロシラン、メチルジフェニルクロロシラン、クロロメチルジメチルクロロシラン等のクロロシラン類、トリメチルメトキシシラン、ジメチルジエトキシシラン、メチルジメトキシシラン、ジメチルビニルエトキシシラン等のアルコキシシラン類、ヘキサメチルジシラザン、N,N’-ビス(トリメチルシリル)ウレア、ジメチルトリメチルシリルアミン、トリメチルシリルイミダゾール等のシラザン類、γ-クロロプロピルトリメトキシシラン、γ-アミノプロピルトリエトキシシラン、γ-グリシドキシプロピルトリメトキシシラン等のその他のシラン類、ベンゾトリアゾール、ベンズイミダゾール、インダゾール、イミダゾール、2-メルカプトベンズイミダゾール、2ーメルカプトベンゾチアゾール、2-メルカプトベンゾオキサゾール、ウラゾール、チオウラシル、メルカプトイミダゾール、メルカプトピリミジン等の複素環式化合物や、1,1-ジメチルウレア、1,3-ジメチルウレア等の尿素、又はチオ尿素化合物を挙げることができる。
これらの接着補助剤が使用される場合、その添加量は、シリコン含有レジスト下層膜形成用組成物の膜形成成分に対して通常5質量%未満、好ましくは2質量%未満である。
また、pH調整剤として、前述の安定化剤として挙げた有機酸などのカルボン酸基を1又は2以上有する酸の他を挙げることができる。pH調整剤が使用される場合のその添加量は、[A]ポリシロキサンの100質量部に対して、0.01~20質量部、又は0.01~10質量部、又は0.01~5質量部の割合とすることができる。
またシリコン含有レジスト下層膜形成用組成物に添加可能な金属酸化物としては、例えば、スズ(Sn)、チタン(Ti)、アルミニウム(Al)、ジルコニウム(Zr)、亜鉛(Zn)、ニオブ(Nb)、タンタル(Ta)及びW(タングステン)等の金属及びホウ素(B)、ケイ素(Si)、ゲルマニウム(Ge)、ヒ素(As)、アンチモン(Sb)、及びテルル(Te)等の半金属のうち1種又は2種以上の組み合わせの酸化物を挙げることができるが、これらに限定されない。
膜形成成分中の[A]ポリシロキサンの含有量は、通常20質量%~100質量%であるが、本発明の効果を再現性よく得る観点等から、その下限値は、好ましくは50質量%、より好ましくは60質量%、より一層好ましくは70質量%、更に好ましくは80質量%であり、その上限値は、好ましくは99質量%であり、その余を、後述の添加剤とすることができる。
また当該シリコン含有レジスト下層膜形成用組成物は、好ましくはpH2~5を有し、より好ましくはpH3~4を有する。
混合順序は特に限定されるものではない。例えば、[A]ポリシロキサンを含有する溶液に、[B]スルホン酸化合物と、pKaが-15.0~1.2の酸とから選ばれる少なくとも1種(例えば、硫酸と、スルホン酸化合物とから選ばれる少なくとも1種)、及び[C]溶媒を加えて混合し、その混合物にその他の成分を加えてもよく、[A]ポリシロキサンを含有する溶液と、[B]スルホン酸化合物と、pKaが-15.0~1.2の酸とから選ばれる少なくとも1種(例えば、硫酸と、スルホン酸化合物とから選ばれる少なくとも1種)と、[C]溶媒と、その他の成分を同時に混合してもよい。
必要であれば、最後に更に[C]溶媒を追加で加えたり、[C]溶媒に比較的溶けやすい一部の成分を混合物中に含めずにおき、最後にそれを加えたりしてもよいが、構成成分の凝集や分離を抑制し、均一性に優れる組成物を再現性よく調製する観点から、[A]ポリシロキサンが良好に溶解した溶液を予め準備し、これを用いて組成物を調製することが好ましい。なお、[A]ポリシロキサンは、共に混ぜられる[B]スルホン酸化合物と、pKaが-15.0~1.2の酸とから選ばれる少なくとも1種(例えば、硫酸と、スルホン酸化合物とから選ばれる少なくとも1種)及び[C]溶媒の種類や量、その他の成分の量や性質等によっては、これらが混ぜられた際に凝集又は沈殿する可能性がある点に留意する。また、[A]ポリシロキサンが溶解した溶液を用いて組成物を調製する場合、最終的に得られる組成物中の[A]ポリシロキサンが所望の量となるように、[A]ポリシロキサンの溶液の濃度やその使用量を決める必要がある点も留意する。
組成物の調製において、成分が分解したり変質したりしない範囲で、適宜加熱してもよい。
以下、本発明の一態様として、本発明のシリコン含有レジスト下層膜形成用組成物を使用したパターン形成方法、並びに、半導体装置の製造方法について説明する。
焼成する条件としては、焼成温度40℃~400℃、又は80℃~250℃、焼成時間0.3分間~60分間の中から適宜選択される。好ましくは、焼成温度150℃~250℃、焼成時間0.5分間~2分間である。
ここで形成されるレジスト下層膜の膜厚としては、例えば、10nm~1,000nmであり、又は20nm~500nmであり、又は50nm~300nmであり、又は100nm~200nm、又は10~150nmである。
なおレジスト下層膜の形成時に使用するシリコン含有レジスト下層膜形成用組成物として、ナイロンフィルタろ過したシリコン含有レジスト下層膜形成用組成物を用いることができる。ここでナイロンフィルタろ過したシリコン含有レジスト下層膜形成用組成物とは、シリコン含有レジスト下層膜形成用組成物を製造する途中の段階において、又は全ての成分を混合した後に、ナイロンフィルタろ過を行った組成物を指す。
ここで使用する有機下層膜としては、特に制限はなく、これまでリソグラフィープロセスにおいて慣用されているものの中から任意に選択して使用することができる。
基板上に、有機下層膜、その上にレジスト下層膜、さらにその上に後述するレジスト膜を設けた態様とすることにより、フォトレジスト膜のパターン幅が狭くなり、パターン倒れを防ぐ為にフォトレジスト膜を薄く被覆した場合でも、後述する適切なエッチングガスを選択することにより基板の加工が可能になる。例えば、フォトレジスト膜に対して十分に早いエッチング速度を有するフッ素系ガスをエッチングガスとして用いて、レジスト下層膜の加工が可能であり、またレジスト下層膜に対して十分に早いエッチング速度を有する酸素系ガスをエッチングガスとして用いて、有機下層膜の加工が可能であり、更に有機下層膜に対して十分に早いエッチング速度を有するフッ素系ガスをエッチングガスとして用いて、基板の加工を行うことができる。
なお、この際に用い得る基板及び塗布方法は、上述したものと同じものが挙げられる。
レジスト膜の膜厚は、例えば10nm~10,000nmであり、又は100nm~2,000nmであり、又は200nm~1,000nmであり、又は30nm~200nmである。
市販品として入手可能な具体例としては、シプレー社製商品名APEX-E、住友化学(株)製商品名PAR710、JSR(株)製;商品名AR2772JN、及び信越化学工業(株)製商品名SEPR430等が挙げられるが、これらに限定されない。また、例えば、Proc.SPIE,Vol.3999,330-334(2000)、Proc.SPIE,Vol.3999,357-364(2000)、やProc.SPIE,Vol.3999,365-374(2000)に記載されているような、含フッ素原子ポリマー系フォトレジスト材料を挙げることができる。
電子線レジスト膜を形成するための電子線レジスト材料としては、ネガ型材料、ポジ型材料いずれも使用できる。その具体例としては、酸発生剤と酸により分解してアルカリ溶解速度を変化させる基を有するバインダーからなる化学増幅型レジスト材料、アルカリ可溶性バインダーと酸発生剤と酸により分解してレジスト材料のアルカリ溶解速度を変化させる低分子化合物からなる化学増幅型レジスト材料、酸発生剤と酸により分解してアルカリ溶解速度を変化させる基を有するバインダーと酸により分解してレジスト材料のアルカリ溶解速度を変化させる低分子化合物からなる化学増幅型レジスト材料、電子線によって分解してアルカリ溶解速度を変化させる基を有するバインダーからなる非化学増幅型レジスト材料、電子線によって切断されアルカリ溶解速度を変化させる部位を有するバインダーからなる非化学増幅型レジスト材料などがある。これらの電子線レジスト材料を用いた場合も、照射源を電子線としてフォトレジスト材料を用いた場合と同様にレジスト膜のパターンを形成することができる。
またEUVレジスト膜を形成するためのEUVレジスト材料としては、メタクリレート樹脂系レジスト材料を用いることができる。
露光後、必要に応じて露光後加熱(post exposure bake)を行うこともできる。露光後加熱は、加熱温度70℃~150℃、加熱時間0.3分間~10分間から適宜選択された条件で行われる。
現像液(アルカリ現像液)としては、水酸化カリウム、水酸化ナトリウムなどのアルカリ金属水酸化物の水溶液、水酸化テトラメチルアンモニウム、水酸化テトラエチルアンモニウム、コリンなどの水酸化四級アンモニウムの水溶液、エタノールアミン、プロピルアミン、エチレンジアミンなどのアミン水溶液等のアルカリ性水溶液(アルカリ現像液)等を例として挙げることができる。さらに、これらの現像液に界面活性剤などを加えることもできる。現像の条件としては、温度5~50℃、時間10秒~600秒から適宜選択される。
現像液(有機溶剤)としては、例えば、酢酸メチル、酢酸ブチル、酢酸エチル、酢酸イソプロピル、酢酸アミル、酢酸イソアミル、メトキシ酢酸エチル、エトキシ酢酸エチル、プロピレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート、エチレングリコールモノプロピルエーテルアセテート、エチレングリコールモノブチルエーテルアセテート、エチレングリコールモノフェニルエーテルアセテート、ジエチレングリコールモノメチルエーテルアセテート、ジエチレングリコールモノプロピルエーテルアセテート、ジエチレングリコールモノエチルエーテルアセテート、ジエチレングリコールモノフェニルエーテルアセテート、ジエチレングリコールモノブチルエーテルアセテート、ジエチレングリコールモノエチルエーテルアセテート、2-メトキシブチルアセテート、3-メトキシブチルアセテート、4-メトキシブチルアセテート、3-メチル-3-メトキシブチルアセテート、3-エチル-3-メトキシブチルアセテート、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、プロピレングリコールモノプロピルエーテルアセテート、2-エトキシブチルアセテート、4-エトキシブチルアセテート、4-プロポキシブチルアセテート、2-メトキシペンチルアセテート、3-メトキシペンチルアセテート、4-メトキシペンチルアセテート、2-メチル-3-メトキシペンチルアセテート、3-メチル-3-メトキシペンチルアセテート、3-メチル-4-メトキシペンチルアセテート、4-メチル-4-メトキシペンチルアセテート、プロピレングリコールジアセテート、ギ酸メチル、ギ酸エチル、ギ酸ブチル、ギ酸プロピル、乳酸エチル、乳酸ブチル、乳酸プロピル、炭酸エチル、炭酸プロピル、炭酸ブチル、ピルビン酸メチル、ピルビン酸エチル、ピルビン酸プロピル、ピルビン酸ブチル、アセト酢酸メチル、アセト酢酸エチル、プロピオン酸メチル、プロピオン酸エチル、プロピオン酸プロピル、プロピオン酸イソプロピル、2-ヒドロキシプロピオン酸メチル、2-ヒドロキシプロピオン酸エチル、メチル-3-メトキシプロピオネート、エチル-3-メトキシプロピオネート、エチル-3-エトキシプロピオネート、プロピル-3-メトキシプロピオネート等を例として挙げることができる。さらに、これらの現像液に界面活性剤などを加えることもできる。現像の条件としては、温度は5℃~50℃、時間は10秒~600秒から適宜選択される。
なおレジスト下層膜のドライエッチングには、ハロゲン系ガスを使用することが好ましい。ハロゲン系ガスによるドライエッチングでは、基本的に有機物質からなるレジスト膜(フォトレジスト膜)は除去されにくい。それに対し、ケイ素原子を多く含むレジスト下層膜はハロゲン系ガスによって速やかに除去される。そのため、該レジスト下層膜のドライエッチングに伴うフォトレジスト膜の膜厚の減少を抑えることができる。そして、その結果、フォトレジスト膜を薄膜で使用することが可能となる。従って、レジスト下層膜のドライエッチングはフッ素系ガスによることが好ましく、フッ素系ガスとしては、例えば、テトラフルオロメタン(CF4)、パーフルオロシクロブタン(C4F8)、パーフルオロプロパン(C3F8)、トリフルオロメタン、ジフルオロメタン(CH2F2)等が挙げられるが、これらに限定されない。
フッ素系ガスとしては、例えば、テトラフルオロメタン(CF4)、パーフルオロシクロブタン(C4F8)、パーフルオロプロパン(C3F8)、トリフルオロメタン、及びジフルオロメタン(CH2F2)等が挙げられる。
レジスト下層膜のドライエッチングは、パターン化において挙げたようにフッ素系ガスによることが好ましく、例えば、テトラフルオロメタン(CF4)、パーフルオロシクロブタン(C4F8)、パーフルオロプロパン(C3F8)、トリフルオロメタン、ジフルオロメタン(CH2F2)等が挙げられるが、これらに限定されない。
本発明にあっては、[B]スルホン酸化合物と、pKaが-15.0~1.2の酸とから選ばれる少なくとも1種(例えば、硫酸と、スルホン酸化合物とから選ばれる少なくとも1種)をシリコン含有レジスト下層膜形成用組成物に配合することにより、該組成物から形成した膜の湿式法による除去性を高めることができる。
レジスト下層膜のウェットエッチングに使用される薬液としては、希フッ酸(フッ化水素酸)、バッファードフッ酸(HFとNH4Fの混合溶液)、塩酸と過酸化水素を含有する水溶液(SC-2薬液)、硫酸と過酸化水素を含有する水溶液(SPM薬液)、弗酸と過酸化水素を含有する水溶液(FPM薬液)や、アンモニアと過酸化水素を含有する水溶液(SC-1薬液)等のアルカリ性溶液が挙げられる。またアルカリ性溶液としては、前述のアンモニアと過酸化水素水と水の混合によるアンモニア過水(SC-1薬液)のほか、アンモニア、テトラメチルアンモニウムヒドロキシド(TMAH)、テトラエチルアンモニウムヒドロキシド、テトラプロピルアンモニウムヒドロキシド、テトラブチルアンモニウムヒドロキシド、コリンヒドロキシド、ベンジルトリメチルアンモニウムヒドロキシド、ベンジルトリエチルアンモニウムヒドロキシド、DBU(ジアザビシクロウンデセン)、DBN(ジアザビシクロノネン)、ヒドロキシルアミン、1-ブチル-1-メチルピロリジニウムヒドロキシド、1-プロピル-1-メチルピロリジニウムヒドロキシド、1-ブチル-1-メチルピペリジニウムヒドロキシド、1-プロピル-1-メチルピペリジニウムヒドロキシド、メピクアトヒドロキシド、トリメチルスルホニウムヒドロキシド、ヒドラジン類、エチレンジアミン類、又はグアニジンを1~99質量%含有する水溶液を挙げることができる。これら薬液は混合して用いることもできる。
さらにレジスト下層膜は、基板とレジスト膜(フォトレジスト膜等)との相互作用を防止するための層、レジスト膜に用いられる材料又はレジスト膜への露光時に生成する物質の基板への悪作用を防ぐ機能を有する層、加熱焼成時に基板から生成する物質のレジスト膜への拡散を防ぐ機能を有する層、及び半導体基板誘電体層によるレジスト膜のポイズニング効果を減少させるためのバリア層等として使用することも可能である。
また本発明のレジスト下層膜は、EUVレジスト膜の下層膜として、ハードマスクとしての機能以外にも、例えばEUVレジスト膜とインターミキシングすることなく、EUV露光(波長13.5nm)に際して好ましくない露光光、例えばUV(紫外)光やDUV(深紫外)光(:ArF光、KrF光)の基板又は界面からの反射を防止することができる。従って、EUVレジスト膜の下層反射防止膜を形成するために、本発明のシリコン含有レジスト下層膜形成用組成物を好適に用いることができる。すなわちEUVレジスト膜の下層として効率的に反射を防止することができる。EUVレジスト下層膜として用いた場合は、そのプロセスはフォトレジスト用下層膜と同様に行うことができる。
また、上述した通りの、有機下層膜を形成する工程と、該有機下層膜上に、本発明のシリコン含有レジスト下層膜形成用組成物を用いてレジスト下層膜を形成する工程と、当該シレジスト下層膜上に、レジスト膜を形成する工程とを含む、半導体素子の製造方法によれば、精度の高い半導体基板の加工を再現性よく実現できるため、半導体素子の安定的な製造を期待できる。
(1)分子量測定
本発明で用いるポリシロキサンの分子量は、GPC分析によるポリスチレン換算で得られる分子量である。
GPCの測定条件は、例えばGPC装置(商品名HLC-8220GPC、東ソー株式会社製)、GPCカラム(商品名Shodex(登録商標)KF803L、KF802、KF801、昭和電工株式会社製)、カラム温度は40℃、溶離液(溶出溶媒)はテトラヒドロフラン、流量(流速)は1.0mL/min、標準試料はポリスチレン(昭和電工株式会社製)を用いて行うことができる。
(2)1H-NMR
JEOL製核磁気共鳴装置1H-NMR(400MHz)、溶媒はd6-Acetoneを用いて評価した。
(3)残硝酸量
イオンクロマトグラフィー評価にて系内に残存する硝酸量を測定した。
(合成例1)
テトラエトキシシラン23.26g、メチルトリエトキシシラン7.11g、フェニルトリメトキシシラン1.58g及びプロピレングリコールモノエチルエーテル47.93gを300mLのフラスコに入れ、得られた混合溶液をマグネチックスターラーにて撹拌しながら0.1M硝酸水溶液20.12gを滴下した。
滴下後、60℃に調整されたオイルバスにフラスコを移し、20時間還流させた。その後、反応副生物である、エタノール、メタノール、及び水を減圧留去し、濃縮して加水分解縮合物(ポリマー)溶液を得た。
得られた溶液に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100%の溶媒比率として140℃における固形残物換算で20質量パーセントとなるように濃度調整し、ナイロン製フィルタ(孔径0.1μm)にてろ過を行った。
得られたポリマーは下記式で表される構造を含むポリシロキサンを含み、その重量平均分子量は、GPCによるポリスチレン換算で3,000であった。また、1H-NMRよりプロピレングリコールモノエチルエーテルによりキャッピングされている量はSi原子に対して3mol%であった。またポリマー溶液中の残硝酸量は1,200ppmであった。
テトラエトキシシラン23.0g、メチルトリエトキシシラン7.0g、ビシクロ[2.2.1]ヘプト-5-エン-2-イルトリエトキシシラン2.02g及びプロピレングリコールモノエチルエーテル48.1gを300mLのフラスコに入れ、得られた混合溶液をマグネチックスターラーにて撹拌しながら硝酸水溶液(0.1mol/L)19.9gを滴下した。
滴下後、60℃に調整されたオイルバスにフラスコを移し、20時間還流させた。その後、反応副生物である、エタノール、及び水を減圧留去し、濃縮して加水分解縮合物(ポリマー)溶液を得た。
得らえた溶液に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100%の溶媒比率として140℃における固形残物換算で20質量パーセントとなるように濃度調整し、ナイロン製フィルタ(孔径0.1μm)にてろ過を行った。
得られたポリマーは下記式で表される構造を含むポリシロキサンを含み、その重量平均分子量は、GPCによるポリスチレン換算でMw2,800であった。また、1H-NMRよりプロピレングリコールモノエチルエーテルによりキャッピングされている量はSi原子に対して3mol%であった。またポリマー溶液中の残硝酸量は1,200ppmであった。
テトラエトキシシラン22.3g、メチルトリエトキシシラン6.82g、ジアリルイソシアヌレートプロピルトリエトキシシラン3.16g及びプロピレングリコールモノエチルエーテル48.4gを300mLのフラスコに入れ、得られた混合溶液をマグネチックスターラーにて撹拌しながら硝酸水溶液(0.1mol/L)19.3gを滴下した。
滴下後、60℃に調整されたオイルバスにフラスコを移し、20時間還流させた。その後、反応副生物である、エタノール、及び水を減圧留去し、濃縮して加水分解縮合物(ポリマー)溶液を得た。
得られた溶液に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100%の溶媒比率として140℃における固形残物換算で20質量パーセントとなるように濃度調整し、ナイロン製フィルタ(孔径0.1μm)にてろ過を行った。
得られたポリマーは下記式で表される構造を含むポリシロキサンを含み、その重量平均分子量は、GPCによるポリスチレン換算でMw2,300であった。また、1H-NMRよりプロピレングリコールモノエチルエーテルによりキャッピングされている量はSi原子に対して2mol%であった。またポリマー溶液中の残硝酸量は1,200ppmであった。
テトラエトキシシラン23.0g、メチルトリエトキシシラン7.02g、チオシアネートプロピルトリエトキシシラン2.07g及びプロピレングリコールモノエチルエーテル48.0gを300mLのフラスコに入れ、得られた混合溶液をマグネチックスターラーにて撹拌しながら硝酸水溶液(0.1mol/L)19.9gを滴下した。
滴下後、60℃に調整されたオイルバスにフラスコを移し、20時間還流させた。その後、反応副生物である、エタノール、及び水を減圧留去し、濃縮して加水分解縮合物(ポリマー)溶液を得た。
該溶液に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100%の溶媒比率として140℃における固形残物換算で20質量パーセントとなるように濃度調整し、ナイロン製フィルタ(孔径0.1μm)にてろ過を行った。
得られたポリマーは下記式で表される構造を含むポリシロキサンを含み、その重量平均分子量は、GPCによるポリスチレン換算でMw2,600であった。また、1H-NMRよりプロピレングリコールモノエチルエーテルによりキャッピングされている量はSi原子に対して3mol%であった。またポリマー溶液中の残硝酸量は1,200ppmであった。
テトラエトキシシラン22.6g、メチルトリエトキシシラン6.62g、トリエトキシ((2-メトキシ-4-(メトキシメチル)フェノキシ)メチル)シラン2.66g及びプロピレングリコールモノエチルエーテル48.3gを300mLのフラスコに入れ、得られた混合溶液をマグネチックスターラーにて撹拌しながら硝酸水溶液(0.1mol/L)19.5gを滴下した。
滴下後、60℃に調整されたオイルバスにフラスコを移し、20時間還流させた。その後、反応副生物である、エタノール、及び水を減圧留去し、濃縮して加水分解縮合物(ポリマー)溶液を得た。
得られた溶液に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100%の溶媒比率として140℃における固形残物換算で20質量パーセントとなるように濃度調整し、ナイロン製フィルタ(孔径0.1μm)にてろ過を行った。
得られたポリマーは下記式で表される構造を含むポリシロキサンを含み、その重量平均分子量は、GPCによるポリスチレン換算でMw3,200であった。また、1H-NMRよりプロピレングリコールモノエチルエーテルによりキャッピングされている量はSi原子に対して4mol%であった。またポリマー溶液中の残硝酸量は1,200ppmであった。
テトラエトキシシラン23.0g、メチルトリエトキシシラン7.04g、エポキシシクロヘキシルエチルトリメトキシシラン1.95g及びプロピレングリコールモノエチルエーテル48.0gを300mLのフラスコに入れ、得られた混合溶液をマグネチックスターラーにて撹拌しながら硝酸水溶液(0.1mol/L)19.9gを滴下した。
滴下後、60℃に調整されたオイルバスにフラスコを移し、20時間還流させた。その後、反応副生物である、エタノール、メタノール、及び水を減圧留去し、濃縮して加水分解縮合物(ポリマー)溶液を得た。
得らえた溶液に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100%の溶媒比率として140℃における固形残物換算で20質量パーセントとなるように濃度調整し、ナイロン製フィルタ(孔径0.1μm)にてろ過を行った。
得られたポリマーは下記式で表される構造を含むポリシロキサンを含み、その重量平均分子量は、GPCによるポリスチレン換算でMw3,100であった。また、1H-NMRよりプロピレングリコールモノエチルエーテルによりキャッピングされている量はSi原子に対して3mol%であった。またポリマー溶液中の残硝酸量は1,200ppmであった。
テトラエトキシシラン23.1g、メチルトリエトキシシラン7.06g、グリシドキシプロピルトリメトキシシラン1.87g及びプロピレングリコールモノエチルエーテル48.0gを300mLのフラスコに入れ、得られた混合溶液をマグネチックスターラーにて撹拌しながら硝酸水溶液(0.1mol/L)20.0gを滴下した。
滴下後、60℃に調整されたオイルバスにフラスコを移し、20時間還流させた。その後、反応副生物である、エタノール、メタノール、及び水を減圧留去し、濃縮して加水分解縮合物(ポリマー)溶液を得た。
得られた溶液に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100%の溶媒比率として140℃における固形残物換算で20質量パーセントとなるように濃度調整し、ナイロン製フィルタ(孔径0.1μm)にてろ過を行った。
得られたポリマーは下記式で表される構造を含むポリシロキサンを含み、その重量平均分子量は、GPCによるポリスチレン換算でMw3,000であった。また、1H-NMRよりプロピレングリコールモノエチルエーテルによりキャッピングされている量はSi原子に対して3mol%であった。またポリマー溶液中の残硝酸量は1,200ppmであった。
テトラエトキシシラン23.3g、メチルトリエトキシシラン6.9g、フェニルトリメトキシシラン1.6g及びプロピレングリコールモノメチルエーテル47.9gを300mLのフラスコに入れ、得られた混合溶液をマグネチックスターラーにて撹拌しながらジメチルアミノプロピルトリメトキシシラン0.29gと硝酸水溶液(0.2mol/L)20.2gを滴下した。
滴下後、60℃に調整されたオイルバスにフラスコを移し、20時間還流させた。その後、反応副生物である、エタノール、メタノール、及び水を減圧留去し、濃縮して加水分解縮合物(ポリマー)溶液を得た。
得られた溶液に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、プロピレングリコールモノメチルエーテル100%の溶媒比率として140℃における固形残物換算で20質量パーセントとなるように濃度調整し、ナイロン製フィルタ(孔径0.1μm)にてろ過を行った。
得られたポリマーは下記式で表される構造を含むポリシロキサンを含み、その重量平均分子量は、GPCによるポリスチレン換算でMw3,000であった。また、1H-NMRよりプロピレングリコールモノメチルエーテルによりキャッピングされている量はSi原子に対して4mol%であった。またポリマー溶液中の残硝酸量は1,200ppmであった。
合成例で得られたポリシロキサン(ポリマー)、酸(添加剤1)、光酸発生剤(添加剤2)、及び溶媒を表1-1又は表1-2に示す割合で混合し、0.1μmのフッ素樹脂製のフィルタでろ過することによって、レジストパターンに塗布される組成物をそれぞれ調製した。表1-1及び表1-2中の各添加量は質量部で示した。
なお、加水分解縮合物(ポリマー)は合成例で得た該縮合物を含む溶液として組成物を調製しているが、表1-1及び表1-2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。
DIW:超純水
PGEE:プロピレングリコールモノエチルエーテル
PGME:プロピレングリコールモノメチルエーテル
MA:マレイン酸
TPSNO3:トリフェニルスルホニウム硝酸塩
TPSML:トリフェニルスルホニウムマレイン酸塩
TPSTfAc:トリフェニルスルホニウムトリフルオロ酢酸塩
IMTEOS:トリエトキシシリルプロピル-4,5-ジヒドロイミダゾール
TPSAc:トリフェニルスルホニウム酢酸塩
BTEAC:ベンジルトリエチルアンモニウムクロライド塩
TPSCl:トリフェニルスルホニウムクロライド塩
5SSA:5-スルホサリチル酸
PSA:4-フェノールスルホン酸
CSA:10-カンファースルホン酸
Tf:トリフルオロメタンスルホン酸
SCA:4-スルホ[4]カリックスアレーン(4量体)
HPS:3-ヒドロキシプロパンスルホン酸
PyS:ピリジン-3-スルホン酸
SPTHOS:3-(トリヒドロキシシリル)-1-プロパンスルホン酸
SA:硫酸
MS:メタンスルホン酸
TFBA:テトラフルオロホウ酸
HFPA:ヘキサフルオロリン酸
PCA:過塩素酸
PIA:過ヨウ素酸
TFSI:ビストリフルオロメタンスルホンイミド酸(Bis(trifluoromethanesulfonyl)imide、CAS RN: 82113-65-3)
上記酸の中でも最も高いpKa(低い酸性度)を有する酸は、10-カンファースルホン酸でありpKa=1.2である。上記の酸の中でも最も低いpKa(高い酸性度)を有する酸は、ビストリフルオロメタンスルホンイミド酸であり、pKa=-15.0である。
Py:ピリジン
TPSOH:トリフェニルスルホニウム水酸化物
TBAOH:テトラブチルアンモニウム水酸化物
TBPOH:テトラブチルホスホニウム水酸化物
DPIOH:ジフェニルヨードニウム水酸化物
窒素下、100mlの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)、及び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℃まで放冷した。
冷却した反応混合物に、クロロホルム(34g、関東化学(株)製)を加えて希釈し、希釈した混合物をメタノール(168g、関東化学(株)製)に添加して沈殿させた。
得られた沈殿物をろ過して回収し、回収した固体を減圧乾燥機で80℃、24時間乾燥し、目的とする式(X)で表されるポリマー(以下PCzFLと略す)9.37gを得た。
なお、PCzFLの1H-NMRの測定結果は以下の通りであった。
1H-NMR(400MHz,DMSO-d6):δ7.03-7.55(br,12H),δ7.61-8.10(br,4H),δ11.18(br,1H)
また、PCzFLの重量平均分子量Mwは、GPCによるポリスチレン換算では2,800、多分散度Mw/Mnは1.77であった。
実施例1~15及び比較例1で調製した組成物を、スピナーを用いてシリコンウエハ上にそれぞれ塗布した。ホットプレート上で215℃1分間加熱し、Si含有レジスト下層膜をそれぞれ形成し、得られた下層膜の膜厚を計測した。
その後、各Si含有レジスト下層膜上に、プロピレングリコールモノメチルエーテル/プロピレングリコールモノメチルエーテルアセテートの混合溶媒(7/3(V/V))を塗布してスピン乾燥した。塗布後の下層膜の膜厚を計測し、混合溶媒塗布前の膜厚を基準(100%)として、混合溶媒塗布後の膜厚の変化の割合(%)を算出した。混合溶媒塗布前後での膜厚変化が1%以下のものを「良好」、膜厚変化が1%超のものを「硬化せず」と評価した。
また同様の方法でシリコンウエハ上に作製した各Si含有レジスト下層膜上に、アルカリ現像液(水酸化テトラメチルアンモニウム(TMAH)2.38%水溶液)を塗布してスピン乾燥し、塗布後の下層膜の膜厚を計測し、現像液塗布前の膜厚を基準(100%)として、現像液塗布後の膜厚の変化の割合(%)を算出した。現像液塗布前後での膜厚変化が1%以下のものを「良好」、膜厚変化が1%超のものを「硬化せず」とした。
得られた結果を表2-1及び表2-2に示す
ウェットエッチング速度の測定では、以下のエッチング薬液を用いた。
TMAH/HF(1:1(質量/質量)) 1質量%混合水溶液
実施例1~15及び比較例1で得られた組成物を、スピナーを用いてシリコンウエハ上にそれぞれ塗布し、ホットプレート上で215℃1分間加熱し、Si含有レジスト下層膜(膜厚0.02μm)をそれぞれ形成した。
得られた各Si含有レジスト下層膜付きシリコンウエハを用い、ウェットエッチング薬液として上述のTMAH/HF混合水溶液を使用して、ウェットエッチング速度を測定した。ウェットエッチレートが5nm/min以上であるものを「良好」、5nm/min未満であるもの「不良」と評価した。得られた結果を表3-1及び表3-2に示す。
シリコンウェハー上に、上記有機下層膜形成用組成物をスピンコートし、ホットプレート上で215℃で1分間加熱することで、有機下層膜(A層)(膜厚90nm)を形成した。
その上に、実施例1で得られた組成物をスピンコートし、ホットプレート上で215℃で1分間加熱することにより、レジスト下層膜(B層)(20nm)を形成した。
更にその上に、EUV用レジスト溶液(メタクリレート樹脂系レジスト)をスピンコートし、110℃で1分間加熱することにより、EUVレジスト膜(C層)を形成し、その後、ASML製EUV露光装置(NXE3300B)を用い、NA=0.33、σ=0.54/0.90、Quadropoleの条件で露光した。
露光後、露光後加熱(PEB、105℃1分間)を行い、クーリングプレート上で室温まで冷却し、TMAH2.38%現像液を用いて30秒現像し、リンス処理をし、レジストパターンを形成した。
パターン形状の観察において、フッティングからアンダーカットの間の形状であり、かつスペース部に著しい残渣がないという状態を「良好」、レジストパターンの下部同士が接触しているという好ましくない状態を「ブリッジ」と評価した。得られた結果を表4に示す。
Claims (18)
- [A]成分:ポリシロキサン
[B]成分:スルホン酸化合物と、pKaが-15.0~1.2の酸とから選ばれる少なくとも1種、及び
[C]成分:溶媒
を含有する、シリコン含有レジスト下層膜形成用組成物。 - [B]成分が、硫酸と、スルホン酸化合物とから選ばれる少なくとも1種である、請求項1に記載のシリコン含有レジスト下層膜形成用組成物。
- [D]成分:硬化触媒を更に含有する、請求項1に記載のシリコン含有レジスト下層膜形成用組成物。
- 前記[D]成分と前記[B]成分との質量比率([D]:[B])が、0.1:1.0~1.0:0.1である、請求項3に記載のシリコン含有レジスト下層膜形成用組成物。
- 前記[B]成分が、ヒドロキシ基を有するスルホン酸化合物を含有する、請求項1に記載のシリコン含有レジスト下層膜形成用組成物。
- 前記[A]成分が、シラノール基の少なくとも一部がアルコール変性された又はアセタール保護されたポリシロキサン変性物を含む、請求項1に記載のシリコン含有レジスト下層膜形成用組成物。
- 前記[C]成分が、アルコール系溶媒を含有する、請求項1に記載のシリコン含有レジスト下層膜形成用組成物。
- 前記[C]成分が、プロピレングリコールモノアルキルエーテルを含有する、請求項7に記載のシリコン含有レジスト下層膜形成用組成物。
- [E]成分:硝酸を更に含有する、請求項1に記載のシリコン含有レジスト下層膜形成用組成物。
- [F]成分:アミンと水酸化物とから選ばれる少なくとも1種を更に含有する、請求項1に記載のシリコン含有レジスト下層膜形成用組成物。
- 前記[C]成分が、水を含有する、請求項1に記載のシリコン含有レジスト下層膜形成用組成物。
- EUVリソグラフィー用レジスト下層膜用である、請求項1に記載のシリコン含有レジスト下層膜形成用組成物。
- 請求項1~12のいずれかに記載のシリコン含有レジスト下層膜形成用組成物の硬化物である、レジスト下層膜。
- 半導体基板と、請求項13に記載のレジスト下層膜とを備える半導体加工用基板。
- 基板上に、有機下層膜を形成する工程と、
前記有機下層膜の上に、請求項1~12のいずれかに記載のシリコン含有レジスト下層膜形成用組成物を用いてレジスト下層膜を形成する工程と、
前記レジスト下層膜の上に、レジスト膜を形成する工程と、
を含む、半導体素子の製造方法。 - 前記レジスト下層膜を形成する工程において、ナイロンフィルタろ過したシリコン含有レジスト下層膜形成用組成物を使用する、
請求項15に記載の半導体素子の製造方法。 - 半導体基板上に有機下層膜を形成する工程と、
前記有機下層膜の上に、請求項1~12のいずれかに記載のシリコン含有レジスト下層膜形成用組成物を塗布し、焼成して、レジスト下層膜を形成する工程と、
前記レジスト下層膜の上に、レジスト膜形成用組成物を塗布し、レジスト膜を形成する工程と、
前記レジスト膜を露光、現像し、レジストパターンを得る工程と、
前記レジストパターンをマスクに用い、前記レジスト下層膜をエッチングする工程と、
パターン化された前記レジスト下層膜をマスクとして用い、前記有機下層膜をエッチングする工程と、
を含む、パターン形成方法。 - 前記有機下層膜をエッチングする工程の後に、薬液を用いた湿式法により前記レジスト下層膜を除去する工程、
を更に含む、請求項17に記載のパターン形成方法。
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