JP6158754B2 - レジスト下層膜形成用組成物、及びパターン形成方法 - Google Patents
レジスト下層膜形成用組成物、及びパターン形成方法 Download PDFInfo
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- JP6158754B2 JP6158754B2 JP2014115506A JP2014115506A JP6158754B2 JP 6158754 B2 JP6158754 B2 JP 6158754B2 JP 2014115506 A JP2014115506 A JP 2014115506A JP 2014115506 A JP2014115506 A JP 2014115506A JP 6158754 B2 JP6158754 B2 JP 6158754B2
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- SZNYYWIUQFZLLT-UHFFFAOYSA-N isopropylmethyl ether Natural products CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 1
- RVPVRDXYQKGNMQ-UHFFFAOYSA-N lead(2+) Chemical compound [Pb+2] RVPVRDXYQKGNMQ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- ZEIWWVGGEOHESL-UHFFFAOYSA-N methanol;titanium Chemical compound [Ti].OC.OC.OC.OC ZEIWWVGGEOHESL-UHFFFAOYSA-N 0.000 description 1
- WVLGTKBIJRAYME-UHFFFAOYSA-N methanolate;yttrium(3+) Chemical compound [Y+3].[O-]C.[O-]C.[O-]C WVLGTKBIJRAYME-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- POPACFLNWGUDSR-UHFFFAOYSA-N methoxy(trimethyl)silane Chemical compound CO[Si](C)(C)C POPACFLNWGUDSR-UHFFFAOYSA-N 0.000 description 1
- YLALLIMOALRHHM-UHFFFAOYSA-N methoxy-dimethyl-(2-phenylethyl)silane Chemical compound CO[Si](C)(C)CCC1=CC=CC=C1 YLALLIMOALRHHM-UHFFFAOYSA-N 0.000 description 1
- REQXNMOSXYEQLM-UHFFFAOYSA-N methoxy-dimethyl-phenylsilane Chemical compound CO[Si](C)(C)C1=CC=CC=C1 REQXNMOSXYEQLM-UHFFFAOYSA-N 0.000 description 1
- HLHZMRQHTSYSST-UHFFFAOYSA-N methoxyantimony Chemical compound CO[Sb] HLHZMRQHTSYSST-UHFFFAOYSA-N 0.000 description 1
- GHAMDDWKPOYZGV-UHFFFAOYSA-N methoxyarsenic Chemical compound CO[As] GHAMDDWKPOYZGV-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- QDIOCYAAOUVXIR-UHFFFAOYSA-N methoxybismuth Chemical compound CO[Bi] QDIOCYAAOUVXIR-UHFFFAOYSA-N 0.000 description 1
- QQKLEWWGQDVDND-UHFFFAOYSA-N methoxytin Chemical compound CO[Sn] QQKLEWWGQDVDND-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- OLXYLDUSSBULGU-UHFFFAOYSA-N methyl pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1 OLXYLDUSSBULGU-UHFFFAOYSA-N 0.000 description 1
- RJMRIDVWCWSWFR-UHFFFAOYSA-N methyl(tripropoxy)silane Chemical compound CCCO[Si](C)(OCCC)OCCC RJMRIDVWCWSWFR-UHFFFAOYSA-N 0.000 description 1
- HLXDKGBELJJMHR-UHFFFAOYSA-N methyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](C)(OC(C)C)OC(C)C HLXDKGBELJJMHR-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- ZIYVHBGGAOATLY-UHFFFAOYSA-N methylmalonic acid Chemical compound OC(=O)C(C)C(O)=O ZIYVHBGGAOATLY-UHFFFAOYSA-N 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 238000001127 nanoimprint lithography Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 229940006477 nitrate ion Drugs 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- VFPUUAVBTSROEQ-UHFFFAOYSA-N octyl(dipropoxy)silane Chemical compound C(CCCCCCC)[SiH](OCCC)OCCC VFPUUAVBTSROEQ-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- IFFPHDYFQRRKPZ-UHFFFAOYSA-N phenol;titanium Chemical compound [Ti].OC1=CC=CC=C1.OC1=CC=CC=C1.OC1=CC=CC=C1.OC1=CC=CC=C1 IFFPHDYFQRRKPZ-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- ZCCUMCLOSRETFE-UHFFFAOYSA-M phenoxyantimony Chemical compound [Sb]OC1=CC=CC=C1 ZCCUMCLOSRETFE-UHFFFAOYSA-M 0.000 description 1
- AVKUWNUBPFREQI-UHFFFAOYSA-N phenoxyarsenic Chemical compound [As]OC1=CC=CC=C1 AVKUWNUBPFREQI-UHFFFAOYSA-N 0.000 description 1
- OXYGVVKTGSCLGP-UHFFFAOYSA-M phenoxybismuth Chemical compound [Bi]OC1=CC=CC=C1 OXYGVVKTGSCLGP-UHFFFAOYSA-M 0.000 description 1
- CSRCVZZUZZRSEH-UHFFFAOYSA-M phenoxytin Chemical compound [Sn]OC1=CC=CC=C1 CSRCVZZUZZRSEH-UHFFFAOYSA-M 0.000 description 1
- FABOKLHQXVRECE-UHFFFAOYSA-N phenyl(tripropoxy)silane Chemical compound CCCO[Si](OCCC)(OCCC)C1=CC=CC=C1 FABOKLHQXVRECE-UHFFFAOYSA-N 0.000 description 1
- VPLNCHFJAOKWBT-UHFFFAOYSA-N phenyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)C1=CC=CC=C1 VPLNCHFJAOKWBT-UHFFFAOYSA-N 0.000 description 1
- 125000005496 phosphonium group Chemical group 0.000 description 1
- 229960004838 phosphoric acid Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- IKNCGYCHMGNBCP-UHFFFAOYSA-N propan-1-olate Chemical compound CCC[O-] IKNCGYCHMGNBCP-UHFFFAOYSA-N 0.000 description 1
- WUBJXWWQGDPUCE-UHFFFAOYSA-N propan-1-olate yttrium(3+) Chemical compound [Y+3].CCC[O-].CCC[O-].CCC[O-] WUBJXWWQGDPUCE-UHFFFAOYSA-N 0.000 description 1
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- NCLVBCYENVSYCE-UHFFFAOYSA-N propoxyantimony Chemical compound CCCO[Sb] NCLVBCYENVSYCE-UHFFFAOYSA-N 0.000 description 1
- PLZKKYRVPOUZSL-UHFFFAOYSA-N propoxybismuth Chemical compound CCCO[Bi] PLZKKYRVPOUZSL-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000001846 repelling effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 125000000123 silicon containing inorganic group Chemical group 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- ASEHKQZNVUOPRW-UHFFFAOYSA-N tert-butyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C(C)(C)C ASEHKQZNVUOPRW-UHFFFAOYSA-N 0.000 description 1
- HXLWJGIPGJFBEZ-UHFFFAOYSA-N tert-butyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C(C)(C)C HXLWJGIPGJFBEZ-UHFFFAOYSA-N 0.000 description 1
- UTIRVQGNGQSJNF-UHFFFAOYSA-N tert-butyl(tripropoxy)silane Chemical compound CCCO[Si](OCCC)(OCCC)C(C)(C)C UTIRVQGNGQSJNF-UHFFFAOYSA-N 0.000 description 1
- HVEXJEOBOQONBC-UHFFFAOYSA-N tert-butyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)C(C)(C)C HVEXJEOBOQONBC-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- GXMNGLIMQIPFEB-UHFFFAOYSA-N tetraethoxygermane Chemical compound CCO[Ge](OCC)(OCC)OCC GXMNGLIMQIPFEB-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- 230000003685 thermal hair damage Effects 0.000 description 1
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- WOZZOSDBXABUFO-UHFFFAOYSA-N tri(butan-2-yloxy)alumane Chemical compound [Al+3].CCC(C)[O-].CCC(C)[O-].CCC(C)[O-] WOZZOSDBXABUFO-UHFFFAOYSA-N 0.000 description 1
- MQVCTPXBBSKLFS-UHFFFAOYSA-N tri(propan-2-yloxy)-propylsilane Chemical compound CCC[Si](OC(C)C)(OC(C)C)OC(C)C MQVCTPXBBSKLFS-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-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
- VBSUMMHIJNZMRM-UHFFFAOYSA-N triethoxy(2-phenylethyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC1=CC=CC=C1 VBSUMMHIJNZMRM-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- BJDLPDPRMYAOCM-UHFFFAOYSA-N triethoxy(propan-2-yl)silane Chemical compound CCO[Si](OCC)(OCC)C(C)C BJDLPDPRMYAOCM-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- USLHPQORLCHMOC-UHFFFAOYSA-N triethoxygallane Chemical compound CCO[Ga](OCC)OCC USLHPQORLCHMOC-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- QFCVQKSWGFVMTB-UHFFFAOYSA-N trihexoxyalumane Chemical compound [Al+3].CCCCCC[O-].CCCCCC[O-].CCCCCC[O-] QFCVQKSWGFVMTB-UHFFFAOYSA-N 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
- LGROXJWYRXANBB-UHFFFAOYSA-N trimethoxy(propan-2-yl)silane Chemical compound CO[Si](OC)(OC)C(C)C LGROXJWYRXANBB-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- UAEJRRZPRZCUBE-UHFFFAOYSA-N trimethoxyalumane Chemical compound [Al+3].[O-]C.[O-]C.[O-]C UAEJRRZPRZCUBE-UHFFFAOYSA-N 0.000 description 1
- XIYWAPJTMIWONS-UHFFFAOYSA-N trimethoxygallane Chemical compound [Ga+3].[O-]C.[O-]C.[O-]C XIYWAPJTMIWONS-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical compound [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- VUWVDNLZJXLQPT-UHFFFAOYSA-N tripropoxy(propyl)silane Chemical compound CCCO[Si](CCC)(OCCC)OCCC VUWVDNLZJXLQPT-UHFFFAOYSA-N 0.000 description 1
- OBROYCQXICMORW-UHFFFAOYSA-N tripropoxyalumane Chemical compound [Al+3].CCC[O-].CCC[O-].CCC[O-] OBROYCQXICMORW-UHFFFAOYSA-N 0.000 description 1
- OZWKZRFXJPGDFM-UHFFFAOYSA-N tripropoxysilane Chemical compound CCCO[SiH](OCCC)OCCC OZWKZRFXJPGDFM-UHFFFAOYSA-N 0.000 description 1
- LTEHWCSSIHAVOQ-UHFFFAOYSA-N tripropyl borate Chemical compound CCCOB(OCCC)OCCC LTEHWCSSIHAVOQ-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- YWIUPWSLDVUCDT-UHFFFAOYSA-N tris(1-methoxyethoxy)alumane Chemical compound [Al+3].COC(C)[O-].COC(C)[O-].COC(C)[O-] YWIUPWSLDVUCDT-UHFFFAOYSA-N 0.000 description 1
- IYGPXXORQKFXCZ-UHFFFAOYSA-N tris(2-methoxyethyl) borate Chemical compound COCCOB(OCCOC)OCCOC IYGPXXORQKFXCZ-UHFFFAOYSA-N 0.000 description 1
- RQNVJDSEWRGEQR-UHFFFAOYSA-N tris(prop-2-enyl) borate Chemical compound C=CCOB(OCC=C)OCC=C RQNVJDSEWRGEQR-UHFFFAOYSA-N 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- HODZVVUWYZMUHG-UHFFFAOYSA-K yttrium(3+) triphenoxide Chemical compound [Y+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 HODZVVUWYZMUHG-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- 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
- H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
- H01L21/3205—Deposition of non-insulating-, e.g. conductive- or resistive-, layers on insulating layers; After-treatment of these layers
- H01L21/321—After treatment
- H01L21/3213—Physical or chemical etching of the layers, e.g. to produce a patterned layer from a pre-deposited extensive layer
- H01L21/32133—Physical or chemical etching of the layers, e.g. to produce a patterned layer from a pre-deposited extensive layer by chemical means only
- H01L21/32135—Physical or chemical etching of the layers, e.g. to produce a patterned layer from a pre-deposited extensive layer by chemical means only by vapour etching only
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/62—Quaternary ammonium compounds
- C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C219/14—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/26—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C219/28—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton having amino groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/12—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of acyclic carbon skeletons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Description
R1B B1R2B B2R3B B3Si(OR0B)(4−B1−B2−B3) (B−1)
(式中、R0Bは炭素数1〜6の炭化水素基であり、R1B、R2B、R3Bは水素原子又は1価の有機基である。また、B1、B2、B3は0又は1であり、0≦B1+B2+B3≦3である。)
なお、本明細書中、Meはメチル基、Etはエチル基、Phはフェニル基を示す。
本発明の4級アンモニウム塩化合物は、下記一般式(A−1)で示される、アントラセン構造を有する4級アンモニウム塩化合物であり、熱架橋促進剤として用いることができる。
具体的にはメチル基、エチル基、ブチル基、イソプロピル基、シクロヘキシル基、アリル基、2−オキソプロピル基、2−オキソ−3−ブテニル基、フェニル基、ナフチル基、アントラセニル基、トリル基、アニシル基、ベンジル基、メトキシベンジル基、ナフチルメチル基、フェネチル基、3−フェニル−2−オキソプロピル基、2−メトキシエチル基、2−[2−メトキシエトキシ]エトキシ基、トリフルオロエチル基、2−ヒドロキシエチル基、2−ヒドロキシプロピル基等を例示できる。
具体的には単結合、メチレン基、エチレン基、プロピレン基、シクロヘキサンジイル基、プロペン−1,3−ジイル基、2−ブテン−1,4−ジイル基、2−オキソプロパン−1,3−ジイル基、1−オキソ−2−プロペン−1,3−ジイル基等を例示できる。更に、ベンゼン、ナフタレン、アントラセン、トルエン、キシレン、トリメチルベンゼン、エチルベンゼン、ベンズアルデヒド、アセトフェノン、エチルメチルエーテル、ジエチルエーテル、ジプロピルエーテル、イソプロピルメチルエーテル、2,2−ジフルオロプロパン、1,1,1−トリフルオロエタン、アニソール、フルオロベンゼン、ギ酸エチル、酢酸メチル、酢酸エチル、酢酸プロピル、酢酸ブチル、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、ブタン酸エチル、安息香酸メチル、安息香酸エチル、安息香酸プロピル、安息香酸トリル、アセトアミド、N−メチルホルムアミド、N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド、N−メチルアセトアミド等から2個の水素原子を除いてできる2価の有機基を例示できる。
具体的には、水酸化物イオン、ギ酸イオン、酢酸イオン、プロピオン酸イオン、ブタン酸イオン、ペンタン酸イオン、ヘキサン酸イオン、ヘプタン酸イオン、オクタン酸イオン、ノナン酸イオン、デカン酸イオン、オレイン酸イオン、ステアリン酸イオン、リノール酸イオン、リノレン酸イオン、安息香酸イオン、p−メチル安息香酸イオン、p−t−ブチル安息香酸イオン、フタル酸イオン、イソフタル酸イオン、テレフタル酸イオン、サリチル酸イオン、トリフルオロ酢酸イオン、ペンタフルオロプロピオン酸イオン、ヘプタフルオロブタン酸イオン、モノクロロ酢酸イオン、ジクロロ酢酸イオン、トリクロロ酢酸イオン、フッ化物イオン、塩化物イオン、臭化物イオン、ヨウ化物イオン、硝酸イオン、塩素酸イオン、過塩素酸イオン、臭素酸イオン、ヨウ素酸イオン、シュウ酸イオン、マロン酸イオン、メチルマロン酸イオン、エチルマロン酸イオン、プロピルマロン酸イオン、ブチルマロン酸イオン、ジメチルマロン酸イオン、ジエチルマロン酸イオン、コハク酸イオン、メチルコハク酸イオン、グルタル酸イオン、アジピン酸イオン、イタコン酸イオン、マレイン酸イオン、フマル酸イオン、シトラコン酸イオン、クエン酸イオン、炭酸イオン、炭酸水素イオン、硫酸水素イオン、p−トルエンスルホン酸イオン、メタンスルホン酸イオン等を例示できる。
最初に、上記A法、即ち、3級アミン化合物の、脱離基を有するアントラセン化合物によるN−アルキル化反応による、上記一般式(A−1a)で表されるアントラセン含有4級アンモニウムカチオンの合成について説明する。
Xは脱離基を示し、具体的には塩素原子、臭素原子、ヨウ素原子などのハロゲン原子;メタンスルホニルオキシ基などのアルキルスルホニルオキシ基;p−トルエンスルホニルオキシ基などのアリールスルホニルオキシ基等を例示できる。
塩基の使用量は、脱離基を有するアントラセン化合物(SA2)1モルに対し、0.3〜10モル、特に0.5〜5モルとすることが望ましい。
触媒を加える場合の添加量は、脱離基を有するアントラセン化合物(SA2)1モルに対し、0.001〜2モル、特に0.005〜0.5モルとすることが望ましい。
次に、上記B法、即ち、材料となる4級アンモニウム塩化合物とアントラセン化合物の縮合反応による上記一般式(A−1a)で表されるアントラセン含有4級アンモニウムカチオンの合成について説明する。
R4A、R4Bは、単結合又は2価の基であり、−R4A−R4B−は−R4−に等しい。例えば、R4がメチレン基である場合、R4AとR4Bは、単結合とメチレン基、又はメチレン基と単結合、の組み合わせである。また例えば、R4がエチレン基である場合、R4AとR4Bは、単結合とエチレン基、メチレン基とメチレン基、又はエチレン基と単結合、の組み合わせである。
また、反応促進のために、反応系中に塩基を添加してもよい。添加する塩基としてはピリジン、トリエチルアミン、ジイソプロピルエチルアミン、4−ジメチルアミノピリジン、イミダゾールなどのアミン類;ナトリウムメトキシド、ナトリウムエトキシド、カリウムt−ブトキシドなどのアルコキシ金属類;炭酸ナトリウム、炭酸カリウム、炭酸セシウムなどの炭酸塩類;水酸化ナトリウム、水酸化カリウム、テトラメチルアンモニウムヒドロキシドなどの水酸化物類;水素化ナトリウム、水素化カリウムなどの金属水素化物類;ブチルリチウム、エチルマグネシウムブロミドなどの有機金属類;リチウムジイソプロピルアミドなどの金属アミド類の中から反応条件により選択して、単独又は2種以上を混合して用いることができる。
塩基の使用量はアントラセン化合物(SA4)1モルに対し、0.3〜10モル、特に0.5〜5モルとすることが望ましい。
触媒を加える場合の添加量は、アントラセン化合物(SA4)1モルに対し、0.001〜2モル、特に0.005〜0.5モルとすることが望ましい。
上記反応により得られるアントラセン構造を有する4級アンモニウムカチオンの対アニオンX−又Z−が、最終目的物である一般式(A−1)で示される本発明の4級アンモニウム塩化合物のアニオン種A−と異なる場合は、追加工程として、下記反応式に示すMm+(A−)mとの反応によるアニオン交換を行うことにより、最終目的物である一般式(A−1)で示される本発明の4級アンモニウム塩化合物を得ることができる。
Mm+はm価の有機カチオン又は無機カチオンを表し、具体的には、ナトリウムイオン、カリウムイオン、リチウムイオン、カルシウムイオン、バリウムイオン、銀イオン、鉛イオン、アンモニウムイオンなどの無機カチオン;テトラメチルアンモニウムイオン、トリエチルアンモニウムイオン、トリフェニルスルホニウムイオン、テトラメチルホスホニウムイオンなどの有機カチオンを例示できる。
反応時間は、液体クロマトグラフィー(LC)や薄層クロマトグラフィー(TLC)により反応を追跡して反応を完結させることが収率の点で望ましいが、通常0.1〜100時間程度である。
また本発明では、上述の本発明の4級アンモニウム塩化合物及びポリシロキサンを含有するレジスト下層膜形成用組成物を提供する。
4級アンモニウム塩化合物の添加量は、ベースポリマー(例えば、後述のポリシロキサン)100質量部に対して、好ましくは0.01〜50質量部、より好ましくは0.1〜40質量部である。
本発明のレジスト下層膜形成用組成物に含有されるポリシロキサンは、下記一般式(B−1)で示される化合物、これの加水分解物、これの縮合物、これの加水分解縮合物のうち1種以上を含有するものであることが好ましい。
R1B B1R2B B2R3B B3Si(OR0B)(4−B1−B2−B3) (B−1)
(式中、R0Bは炭素数1〜6の炭化水素基であり、R1B、R2B、R3Bは水素原子又は1価の有機基である。また、B1、B2、B3は0又は1であり、0≦B1+B2+B3≦3である。)
テトラアルコキシシランとしては、テトラメトキシシラン、テトラエトキシシラン、テトラプロポキシシラン、テトライソプロポキシシラン等を例示できる。
L’(OR4B)B4(OR5B)B5(O)B6 (B−2)
(式中、R4B及びR5Bは水素原子又は炭素数1〜30の有機基であり、B4+B5+B6はL’の種類によって決まる価数であり、B4、B5、B6は0以上の数であり、L’は周期律表のIII族、IV族、又はV族の元素で炭素を除くものである。)
L’がホウ素の場合、一般式(B−2)で示される化合物として、ボロンメトキシド、ボロンエトキシド、ボロンプロポキシド、ボロンブトキシド、ボロンアミロキシド、ボロンヘキシロキシド、ボロンシクロペントキシド、ボロンシクロヘキシロキシド、ボロンアリロキシド、ボロンフェノキシド、ボロンメトキシエトキシド、ホウ酸、酸化ホウ素などを例示できる。
その他に酸触媒を除去する方法として、イオン交換樹脂による方法や、エチレンオキサイド、プロピレンオキサイド等のエポキシ化合物で中和したのち除去する方法を挙げることができる。これらの方法は、反応に使用された酸触媒に合わせて適宜選択することができる。
なお、水溶性有機溶剤と水難溶性有機溶剤との混合割合は、酸触媒を除去する際に用いられるものと同様でよい。
また、このときの水洗操作により、ポリシロキサンの一部が水層に逃げ、実質的に分画操作と同等の効果が得られている場合があるため、水洗回数や洗浄水の量は触媒除去効果と分画効果を鑑みて適宜選択すればよい。
また、ポリシロキサン溶液に加える最終的な溶剤も、酸触媒を用いる場合と同様のものを用いることができる。
また、酸触媒を用いる場合と同様、安定剤を添加してもよい。
なお、有機溶剤を使用する場合は、酸触媒を用いる場合と同様のものを用いることができる。
なお、上記重量平均分子量に関するデータは、検出器としてRI、溶離溶剤としてテトラヒドロフランを用いたゲルパーミエーションクロマトグラフィー(GPC)により、標準物質としてポリスチレンを用いて、ポリスチレン換算で分子量を表したものである。
本発明のレジスト下層膜形成用組成物には、安定性を向上させるために、炭素数が1〜30の1価又は2価以上の有機酸を添加することが好ましい。このような有機酸としては、ギ酸、酢酸、プロピオン酸、ブタン酸、ペンタン酸、ヘキサン酸、ヘプタン酸、オクタン酸、ノナン酸、デカン酸、オレイン酸、ステアリン酸、リノール酸、リノレン酸、安息香酸、フタル酸、イソフタル酸、テレフタル酸、サリチル酸、トリフルオロ酢酸、モノクロロ酢酸、ジクロロ酢酸、トリクロロ酢酸、シュウ酸、マロン酸、メチルマロン酸、エチルマロン酸、プロピルマロン酸、ブチルマロン酸、ジメチルマロン酸、ジエチルマロン酸、コハク酸、メチルコハク酸、グルタル酸、アジピン酸、イタコン酸、マレイン酸、フマル酸、シトラコン酸、クエン酸等を例示することができる。特にシュウ酸、マレイン酸、ギ酸、酢酸、プロピオン酸、クエン酸等が好ましい。また、安定性を保つため、2種以上の酸を混合して使用してもよい。添加量は組成物に含まれるポリシロキサン100質量部に対して0.001〜25質量部が好ましく、より好ましくは0.01〜15質量部、更に好ましくは0.1〜5質量部である。
あるいは、上記有機酸を組成物のpHに換算して、好ましくは0≦pH≦7、より好ましくは0.3≦pH≦6.5、更に好ましくは0.5≦pH≦6となるように配合することが好ましい。
水を含む全溶剤の使用量は、ベースポリマー(ポリシロキサン)100質量部に対して100〜100,000質量部が好ましく、より好ましくは200〜50,000質量部である。このような添加量とすることで、リソグラフィー性能を向上させることができ、かつ塗布膜の均一性が悪化しにくいため、はじきの発生を抑えることができる。
本発明では、被加工体上に塗布型有機下層膜材料を用いて有機下層膜を形成し、該有機下層膜の上に上述の本発明の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し、該レジスト下層膜上にレジストパターンを形成し、該レジストパターンをマスクにして前記レジスト下層膜にドライエッチングでパターンを転写し、該パターンが転写されたレジスト下層膜をマスクにして前記有機下層膜にドライエッチングでパターンを転写し、更に該パターンが転写された有機下層膜をマスクにして前記被加工体にドライエッチングでパターンを転写するパターン形成方法を提供する。
なお、ここでいう塗布型有機下層膜材料とは、材料溶液をスピンコーティング法等によって被加工体上に塗布することで有機下層膜を形成できるものを指す。
このような塗布型有機下層膜材料としては、アントラセン骨格を含有するものを用いることが好ましい。アントラセン骨格を含有する有機下層膜上に本発明の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ことで、更に反射を抑えることができる。
一般式(A−1)で示される本発明の4級アンモニウム塩化合物を以下に示す方法で合成した(合成例1−1〜1−8)。
MALDI−TOF−MS(DCTB/CHCl3):(+)191.1、326.2、(−)35.0。
IR(D−ATR):ν=3083、3054、3023、2995、2968、1624、1481、1454、1439、1413、1351、1340、1261、1222、1050、1039、991、982、972、931、893、854、806、769、747、735、708、652、601cm−1。
1H−NMR(500MHz in DMSO−d6):δ=2.81(6H、s)、5.18(2H、t、J=3Hz)、5.98(2H、s)、7.45−7.53(3H、m)、7.59(2H、dd、J=8、7Hz)、7.65−7.72(4H、m)、8.20(2H、d、J=9Hz)、8.90(3H、m)。
13C−NMR(125MHz in DMSO−d6):δ=48.20、59.02、66.55、119.32、125.08、125.33、127.51、128.43、128.77、129.43、130.18、130.99、131.95、133.03、133.36。
MALDI−TOF−MS(DCTB/CHCl3):(+)191.2、326.2、(−)62.0。
IR(D−ATR):ν=3037、1746、1707、1625、1504、1483、1446、1415、1357、1329、1260、1183、1160、1041、989、956、928、895、856、810、769、741、728、709、655、603cm−1。
1H−NMR(500MHz in DMSO−d6):δ=2,78(6H、s)、4.89(2H、s)、5.82(2H、s)、7.45−7.55(3H、m)、7.60−7.65(4H、m)、7.70−7.75(2H、m)、8.23(2H、d、J=8Hz)、8.66(2H、d、J=10Hz)、8.93(1H、s)。
13C−NMR(125MHz in DMSO−d6):δ=48.50、59.26、67.21、119.07、124.54、125.39、127.66、128.09、128.94、129.61、130.36、131.05、132.11、132.96、133.30。
MALDI−TOF−MS(DCTB/CHCl3):(+)364.2、(−)35.0。
1H−NMR(600MHz in DMSO−d6):δ=1.11(9H、t、J=7Hz)、2.20(2H、m)、3.26(6H、q、J=7Hz)、3.32(2H、m)、4.69(2H、t、J=6Hz)、7.59(2H、br.t、J=8Hz)、7.65(2H、br.t、J=9Hz)、8.04(2H、br.d、8Hz)、8.17(2H、br.d、9Hz)、8.80(1H、s)。
13C−NMR(150MHz in DMSO−d6):δ=7.11、21.01、52.10、53.25、54.93、124.58、125.79、127.21、127.48、127.52、128.66、129.42、130.38、168.45。
MALDI−TOF−MS(DCTB/CHCl3):(+)364.2、(−)62.0。
IR(D−ATR): ν=2987、1721、1625、1523、1448、1397、1341、1264、1206、1174、1153、1039、1015、862、826、796、746cm−1。
1H−NMR(500MHz in DMSO−d6):δ=1.10(9H、br.t、J=7Hz)、2.19(2H、m)、3.21−3.31(8H、m)、4.67(2H、br.t、J=6Hz)、7.59(2H、m)、7.65(2H、m)、8.04(2H、br.d、9Hz)、8.17(2H、br.d、9Hz)、8.80(1H、s)。
13C−NMR(125MHz in DMSO−d6):δ=7.07、20.97、52.08、53.24、62.75、124.63、125.86、127.24、127.53、127.56、128.71、129.47、130.43、168.51。
MALDI−TOF−MS(DCTB/CHCl3):(+)308.2、(−)35.0。
IR(D−ATR): ν=3016、2952、1742、1719、1625、1482、1463、1403、1259、1196、1143、1121、1046、1014、998、958、931、882、867、742、733、702、638、600cm−1。
1H−NMR(600MHz in DMSO−d6):δ=3.27(9H、s)、4.57(2H、s)、6.29(2H、s)、7.57(2H、m)、7.65(2H,m)、8.15(2H、d、J=8Hz)、8.40(2H、d、J=8Hz)、8.74(1H、s)。
13C−NMR(150MHz in DMSO−d6):δ=53.01、60.09、62.42、123.09、124.99、125.35、126.99、129.02、129.45、130.56、130.83、164.99。
IR(D−ATR):ν=3034、2981、1748、1625、1492、1478、1463、1407、1359、1326、1269、1258、1192、1182、1163、1135、1055、1040、1007、997、958、932、906、894、885、868、790、765、733、702cm−1。
1H−NMR(600MHz in DMSO−d6):δ=3.24(9H、s)、4.45(2H、s)、6.30(2H、s)、7.57(2H、m)、7.65(2H,m)、8.15(2H、d、J=9Hz)、8.40(2H、dd、J=9、1Hz)、8.74(1H、s)。
13C−NMR(150MHz in DMSO−d6):δ=53.16、60.12、62.56、123.90、124.96、125.36、126.99、129.02、129.46、130.57、130.84、164.88。
安息香酸1.47g、アセトニトリル16gの混合物に、酸化銀(I)1.39gを加えた後、塩化(9−アントラセニルメチル)トリメチルアンモニウム3.43gを加え、室温で20時間攪拌した。メタノールを加え、不溶分を濾別後、減圧濃縮した。ジイソプロピルエーテルを加えて、析出した結晶を濾取、減圧乾燥し、安息香酸(9−アントラセニルメチル)トリメチルアンモニウム4.26gを得た。
LC−MS(ESI):(+)250、(−)121。
IR(D−ATR):ν=3017、1622、1605、1564、1492、1460、1449、1364、1261、1188、1162、1064、1049、1021、972、946、900、876、868、825、797、750、735、719、670、634、602cm−1。
1H−NMR(500MHz in DMSO−d6):δ=3.13(9H、s)、5.78(2H、s)、7.23(3H、m)、7.58(2H、dd、J=9、7Hz)、7.65(2H、m)、7.87(2H、m)、8.19(2H、d、J=9Hz)、8.81(2H、d、J=9Hz)、8.88(1H、s)。
13C−NMR(125MHz in DMSO−d6):δ=52.70、58.76、119.85、124.96、125.35、126.89、127.46、128.01、128.93、129.40、130.97、131.74、132.82、141.78、168.31。
LC−MS(ESI):(+)250、(−)113。
IR(D−ATR):ν=3032、1682、1667、1626、1526、1507、1496、1481、1450、1413、1120、1167、1119、976、947、924、878、823、802、754、736、715、648、636、602cm−1。
1H−NMR(500MHz in DMSO−d6):δ=3.09(9H、s)、5.69(2H、s)、7.60(2H、dd、J=8、7Hz)、7.70(2H、m)、8.21(2H、d、J=9Hz)、8.72(2H、d、J=9Hz)、8.90(1H、s)。
13C−NMR(125MHz in DMSO−d6):δ=52.73、58.83、117.48(q、J=300Hz)、119.62、124.74、125.35、127.49、129.45、130.96、131.80、132.77、157.91(q、J=30Hz)。
19F−NMR(470MHz in DMSO−d6):δ=−74.79(3F、s)。
一般式(B−1)で示されるポリシロキサンを以下に示す方法で合成した(合成例2−1〜2−3)。
(合成例2−1)ポリシロキサン1の合成
エタノール260g、メタンスルホン酸0.2g、及び脱イオン水260gの混合物にメチルトリメトキシシラン34.1g及びテトラエトキシシラン52.2gの混合物を添加し、12時間、40℃に保持し、加水分解縮合させた。反応終了後、プロピレングリコールエチルエーテル(PGEE)300gを加え、副生アルコール及び過剰の水分を減圧留去し、ポリシロキサン1のPGEE溶液260g(化合物濃度11.2%)を得た。ポリシロキサン1のポリスチレン換算分子量を測定したところMw=2,300であった。
エタノール260g、メタンスルホン酸0.2g、及び脱イオン水260gの混合物にフェニルトリメトキシシラン5.0g及びテトラエトキシシラン99.2gの混合物を添加し、12時間、40℃に保持し、加水分解縮合させた。反応終了後、プロピレングリコールエチルエーテル(PGEE)300gを加え、副生アルコール及び過剰の水分を減圧留去し、ポリシロキサン2のPGEE溶液290g(化合物濃度10.1%)を得た。ポリシロキサン2のポリスチレン換算分子量を測定したところMw=1,900であった。
エタノール260g、メタンスルホン酸0.2g、及び脱イオン水260gの混合物にメチルトリメトキシシラン68.1gを添加し、12時間、40℃に保持し、加水分解縮合させた。反応終了後、プロピレングリコールエチルエーテル(PGEE)300gを加え、副生アルコール及び過剰の水分を減圧留去し、ポリシロキサン3のPGEE溶液310g(化合物濃度10.1%)を得た。ポリシロキサン3のポリスチレン換算分子量を測定したところMw=2,200であった。
上記の合成例2−1〜2−3で得られたポリシロキサン1〜3、熱架橋促進剤として合成例1−1〜1−8で得られた4級アンモニウム塩化合物(S1〜S8)、溶剤、添加物(H2O)を表1に示す割合で混合し、0.1μmのフッ素樹脂製のフィルターで濾過することによって、レジスト下層膜形成用組成物溶液をそれぞれ調製し、それぞれSol.1〜19とした。
Sol.1〜19を回転塗布し、200℃で60秒間加熱して、膜厚80nmのポリシロキサン含有膜(Film1〜19とする)を形成し、J.A.ウーラム社の入射角度可変の分光エリプソメーター(VUV−VASE)で波長248nmにおけるFilm1〜19の光学定数(屈折率n、消衰係数k、反射)を求めた結果を表2に示す。
シリコンウエハー上に、信越化学工業(株)製スピンオンカーボン膜形成用組成物ODL−69(カーボン含有量86質量%)を膜厚2.0μmで塗布し、300℃で60秒間加熱して有機下層膜を形成した。その上にレジスト下層膜形成用組成物として上述のSol.1〜19を塗布し、200℃で60秒間加熱して膜厚80nmのレジスト下層膜としてFilm1〜19を形成した。
次いで、これらをKrF液浸露光装置((株)ニコン製;NSR−S206D(NA=0.68)で露光し、110℃で60秒間ベーク(PEB)し、2.38質量%テトラメチルアンモニウムヒドロキシド(TMAH)水溶液で現像して、130nmのラインアンドスペースパターンを得た。このウエハーの断面形状を(株)日立製作所製電子顕微鏡(S−9380)で測定した結果を表4に示す。
分散度(Mw/Mn)=1.98
PAG2(酸発生剤):ビス(シクロヘキシルスルホニル)ジアゾメタン
Base(塩基性化合物):トリス(2−メトキシエチル)アミン
界面活性剤:FC−4430(住友スリーエム(株)製)
溶剤A:プロピレングリコールメチルエーテルアセテート(PGMEA)
溶剤B:乳酸エチル
Claims (7)
- 下記一般式(A−1)で示される4級アンモニウム塩化合物及びポリシロキサンを含有するものであることを特徴とするレジスト下層膜形成用組成物。
- 前記ポリシロキサンが下記一般式(B−1)で示される化合物、これの加水分解物、これの縮合物、これの加水分解縮合物のうち1種以上を含有するものであることを特徴とする請求項1に記載のレジスト下層膜形成用組成物。
R1B B1R2B B2R3B B3Si(OR0B)(4−B1−B2−B3) (B−1)
(式中、R0Bは炭素数1〜6の炭化水素基であり、R1B、R2B、R3Bは水素原子又は1価の有機基である。また、B1、B2、B3は0又は1であり、0≦B1+B2+B3≦3である。) - 被加工体上に塗布型有機下層膜材料を用いて有機下層膜を形成し、該有機下層膜の上に請求項1又は請求項2に記載の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し、該レジスト下層膜上にレジストパターンを形成し、該レジストパターンをマスクにして前記レジスト下層膜にドライエッチングでパターンを転写し、該パターンが転写されたレジスト下層膜をマスクにして前記有機下層膜にドライエッチングでパターンを転写し、更に該パターンが転写された有機下層膜をマスクにして前記被加工体にドライエッチングでパターンを転写することを特徴とするパターン形成方法。
- 前記塗布型有機下層膜材料として、アントラセン骨格を含有するものを用いることを特徴とする請求項3に記載のパターン形成方法。
- 被加工体上に炭素を主成分とする有機ハードマスクをCVD法で形成し、該有機ハードマスクの上に請求項1又は請求項2に記載の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し、該レジスト下層膜上にレジストパターンを形成し、該レジストパターンをマスクにして前記レジスト下層膜にドライエッチングでパターンを転写し、該パターンが転写されたレジスト下層膜をマスクにして前記有機ハードマスクにドライエッチングでパターンを転写し、更に該パターンが転写された有機ハードマスクをマスクにして前記被加工体にドライエッチングでパターンを転写することを特徴とするパターン形成方法。
- 前記被加工体として、半導体装置基板、又は該半導体装置基板に金属膜、金属炭化膜、金属酸化膜、金属窒化膜、金属酸化炭化膜、及び金属酸化窒化膜のいずれかが成膜されたものを用いることを特徴とする請求項3から請求項5のいずれか一項に記載のパターン形成方法。
- 前記被加工体を構成する金属が、ケイ素、チタン、タングステン、ハフニウム、ジルコニウム、クロム、ゲルマニウム、銅、アルミニウム、インジウム、ガリウム、ヒ素、パラジウム、鉄、タンタル、イリジウム、モリブデン、又はこれらの合金を含むことを特徴とする請求項6に記載のパターン形成方法。
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