JP5229337B2 - 含窒素有機化合物 - Google Patents
含窒素有機化合物 Download PDFInfo
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- JP5229337B2 JP5229337B2 JP2011028107A JP2011028107A JP5229337B2 JP 5229337 B2 JP5229337 B2 JP 5229337B2 JP 2011028107 A JP2011028107 A JP 2011028107A JP 2011028107 A JP2011028107 A JP 2011028107A JP 5229337 B2 JP5229337 B2 JP 5229337B2
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- sulfonate
- nitrogen
- carbon atoms
- bis
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- -1 Nitrogen-containing organic compounds Chemical class 0.000 title claims description 249
- 125000004432 carbon atom Chemical group C* 0.000 claims description 71
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 27
- 125000001033 ether group Chemical group 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000004185 ester group Chemical group 0.000 claims description 20
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 125000004434 sulfur atom Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000004036 acetal group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000002345 steroid group Chemical group 0.000 claims 3
- 239000002253 acid Substances 0.000 description 59
- 239000000463 material Substances 0.000 description 56
- 150000002923 oximes Chemical class 0.000 description 52
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 48
- 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 43
- 239000012953 triphenylsulfonium Substances 0.000 description 43
- 150000001875 compounds Chemical class 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 28
- 238000000034 method Methods 0.000 description 25
- MFNBODQBPMDPPQ-UHFFFAOYSA-N (4-tert-butylphenyl)-diphenylsulfanium Chemical compound C1=CC(C(C)(C)C)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 MFNBODQBPMDPPQ-UHFFFAOYSA-N 0.000 description 23
- 239000002585 base Substances 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- 239000011347 resin Substances 0.000 description 16
- 229920005989 resin Polymers 0.000 description 16
- ADBIXYANGWRBQE-UHFFFAOYSA-N adamantane methoxycarbonyl difluoromethanesulfonate Chemical compound FC(S(=O)(=O)OC(=O)OC)F.C12CC3CC(CC(C1)C3)C2 ADBIXYANGWRBQE-UHFFFAOYSA-N 0.000 description 15
- BCDRHEQJJURKAJ-UHFFFAOYSA-N methoxycarbonyl difluoromethanesulfonate Chemical compound COC(=O)OS(=O)(=O)C(F)F BCDRHEQJJURKAJ-UHFFFAOYSA-N 0.000 description 15
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 15
- 150000003839 salts Chemical class 0.000 description 14
- RSERVFRSDPESLG-UHFFFAOYSA-N 1,1,3,3,3-pentafluoro-2-(naphthalene-2-carbonyloxy)propane-1-sulfonic acid Chemical compound C1=CC=CC2=CC(C(=O)OC(C(F)(F)S(=O)(=O)O)C(F)(F)F)=CC=C21 RSERVFRSDPESLG-UHFFFAOYSA-N 0.000 description 13
- PUKFLHPSERHMCY-UHFFFAOYSA-N 1,1,3,3,3-pentafluoro-2-hydroxypropane-1-sulfonic acid Chemical compound FC(F)(F)C(O)C(F)(F)S(O)(=O)=O PUKFLHPSERHMCY-UHFFFAOYSA-N 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 13
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- YPFJVAAXNOANAU-UHFFFAOYSA-N 2-benzoyloxy-1,1,3,3,3-pentafluoropropane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(C(F)(F)F)OC(=O)C1=CC=CC=C1 YPFJVAAXNOANAU-UHFFFAOYSA-N 0.000 description 11
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 11
- QQMYPHGEZLNMAJ-UHFFFAOYSA-N 2-(cyclohexanecarbonyloxy)-1,1,3,3,3-pentafluoropropane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(C(F)(F)F)OC(=O)C1CCCCC1 QQMYPHGEZLNMAJ-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 10
- 229940077388 benzenesulfonate Drugs 0.000 description 10
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 10
- 238000007654 immersion Methods 0.000 description 10
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- 238000010626 work up procedure Methods 0.000 description 10
- VTMIXGAMEHRTRP-UHFFFAOYSA-N 1,1,1,3,3-pentafluoropropan-2-yl 4-phenylbenzoate Chemical compound C1=CC(C(=O)OC(C(F)F)C(F)(F)F)=CC=C1C1=CC=CC=C1 VTMIXGAMEHRTRP-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 125000005636 nonafluorobutanesulfonate group Chemical group 0.000 description 9
- SEEJHICDPXGSRQ-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6-undecafluoro-6-(1,1,2,2,2-pentafluoroethyl)cyclohexane Chemical compound FC(F)(F)C(F)(F)C1(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F SEEJHICDPXGSRQ-UHFFFAOYSA-N 0.000 description 8
- GGNTZQPZZSOHAN-UHFFFAOYSA-N 1,1,3,3,3-pentafluoro-2-(4-methylphenyl)sulfonyloxypropane-1-sulfonic acid Chemical compound CC1=CC=C(S(=O)(=O)OC(C(F)(F)F)C(F)(F)S(O)(=O)=O)C=C1 GGNTZQPZZSOHAN-UHFFFAOYSA-N 0.000 description 8
- ZVIQVQCAOSPBFT-UHFFFAOYSA-N 1,1-difluoro-2-(4-methylphenyl)sulfonyloxyethanesulfonic acid Chemical compound CC1=CC=C(S(=O)(=O)OCC(F)(F)S(O)(=O)=O)C=C1 ZVIQVQCAOSPBFT-UHFFFAOYSA-N 0.000 description 8
- FJJHRCLHBNAGQE-UHFFFAOYSA-N 1,1-difluoro-2-oxo-2-[(4-oxo-1-adamantyl)oxy]ethanesulfonic acid Chemical compound C1C(C2)CC3CC1(OC(=O)C(F)(F)S(=O)(=O)O)CC2C3=O FJJHRCLHBNAGQE-UHFFFAOYSA-N 0.000 description 8
- JIQGDNAHBPBBMZ-UHFFFAOYSA-N 2-(4-tert-butylbenzoyl)oxy-1,1,3,3,3-pentafluoropropane-1-sulfonic acid Chemical compound CC(C)(C)C1=CC=C(C(=O)OC(C(F)(F)F)C(F)(F)S(O)(=O)=O)C=C1 JIQGDNAHBPBBMZ-UHFFFAOYSA-N 0.000 description 8
- YDOPMIAANRCTID-UHFFFAOYSA-N 2-(adamantane-1-carbonyloxy)-1,1,3,3,3-pentafluoropropane-1-sulfonic acid Chemical compound C1C(C2)CC3CC2CC1(C(=O)OC(C(F)(F)S(=O)(=O)O)C(F)(F)F)C3 YDOPMIAANRCTID-UHFFFAOYSA-N 0.000 description 8
- XZMDYFDOWYDDGM-UHFFFAOYSA-N 2-acetyloxy-1,1,3,3,3-pentafluoropropane-1-sulfonic acid Chemical compound CC(=O)OC(C(F)(F)F)C(F)(F)S(O)(=O)=O XZMDYFDOWYDDGM-UHFFFAOYSA-N 0.000 description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 8
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 8
- 150000003431 steroids Chemical group 0.000 description 8
- MYVMVYSRGHVWED-UHFFFAOYSA-N (5-oxo-4-oxatricyclo[4.2.1.03,7]nonan-2-yl)oxycarbonyl difluoromethanesulfonate Chemical compound O=C1OC2C(OC(=O)OS(=O)(=O)C(F)F)C3CC1C2C3 MYVMVYSRGHVWED-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 229920005601 base polymer Polymers 0.000 description 7
- 238000011161 development Methods 0.000 description 7
- 230000018109 developmental process Effects 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 150000002148 esters Chemical group 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 150000003949 imides Chemical class 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- YFSUTJLHUFNCNZ-UHFFFAOYSA-N perfluorooctane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YFSUTJLHUFNCNZ-UHFFFAOYSA-N 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- XBWQFDNGNOOMDZ-UHFFFAOYSA-N 1,1,2,2,3,3,3-heptafluoropropane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)F XBWQFDNGNOOMDZ-UHFFFAOYSA-N 0.000 description 6
- VMMIZNKPCLNGSS-UHFFFAOYSA-N 1-(2-oxo-2-phenylethyl)tetrahydrothiophenium Chemical compound C=1C=CC=CC=1C(=O)C[S+]1CCCC1 VMMIZNKPCLNGSS-UHFFFAOYSA-N 0.000 description 6
- KZJRKRQSDZGHEC-UHFFFAOYSA-N 2,2,2-trifluoro-1-phenylethanone Chemical compound FC(F)(F)C(=O)C1=CC=CC=C1 KZJRKRQSDZGHEC-UHFFFAOYSA-N 0.000 description 6
- IKMBXKGUMLSBOT-UHFFFAOYSA-M 2,3,4,5,6-pentafluorobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=C(F)C(F)=C(F)C(F)=C1F IKMBXKGUMLSBOT-UHFFFAOYSA-M 0.000 description 6
- FRAXPMHQXQQWOE-UHFFFAOYSA-N 2-(2,2-dimethylpropanoyloxy)-1,1,3,3,3-pentafluoropropane-1-sulfonic acid Chemical compound CC(C)(C)C(=O)OC(C(F)(F)F)C(F)(F)S(O)(=O)=O FRAXPMHQXQQWOE-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 150000007514 bases Chemical class 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000003431 cross linking reagent Substances 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 238000009792 diffusion process Methods 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- GKNWQHIXXANPTN-UHFFFAOYSA-M 1,1,2,2,2-pentafluoroethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)F GKNWQHIXXANPTN-UHFFFAOYSA-M 0.000 description 5
- JGTNAGYHADQMCM-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-M 0.000 description 5
- ZSXYJNYYDJTZPB-UHFFFAOYSA-N 1-(1,1-difluoro-2h-naphthalen-2-yl)ethanesulfonic acid Chemical compound C1=CC=C2C(F)(F)C(C(C)S(O)(=O)=O)C=CC2=C1 ZSXYJNYYDJTZPB-UHFFFAOYSA-N 0.000 description 5
- NCJZVRPXSSYDBG-UHFFFAOYSA-N 2,2,2-trifluoro-1-(4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(=O)C(F)(F)F)C=C1 NCJZVRPXSSYDBG-UHFFFAOYSA-N 0.000 description 5
- YHGKEORTCHVBQH-UHFFFAOYSA-M 2,4,6-tri(propan-2-yl)benzenesulfonate Chemical compound CC(C)C1=CC(C(C)C)=C(S([O-])(=O)=O)C(C(C)C)=C1 YHGKEORTCHVBQH-UHFFFAOYSA-M 0.000 description 5
- LXFQSRIDYRFTJW-UHFFFAOYSA-M 2,4,6-trimethylbenzenesulfonate Chemical compound CC1=CC(C)=C(S([O-])(=O)=O)C(C)=C1 LXFQSRIDYRFTJW-UHFFFAOYSA-M 0.000 description 5
- WVSYONICNIDYBE-UHFFFAOYSA-M 4-fluorobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(F)C=C1 WVSYONICNIDYBE-UHFFFAOYSA-M 0.000 description 5
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- BCRYCJCLIOZGKK-UHFFFAOYSA-N [[1-(9h-fluoren-2-yl)-2,2,3,3,4,4,5,5,6,6-decafluorohexylidene]amino] 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound C1=CC=C2C3=CC=C(C(=NOS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)F)C=C3CC2=C1 BCRYCJCLIOZGKK-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- QDHFHIQKOVNCNC-UHFFFAOYSA-M butane-1-sulfonate Chemical compound CCCCS([O-])(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-M 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000010894 electron beam technology Methods 0.000 description 5
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000000671 immersion lithography Methods 0.000 description 5
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 5
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 5
- WLGDAKIJYPIYLR-UHFFFAOYSA-M octane-1-sulfonate Chemical compound CCCCCCCCS([O-])(=O)=O WLGDAKIJYPIYLR-UHFFFAOYSA-M 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 5
- WMGVPDQNPUQRND-UHFFFAOYSA-N (2-methylphenyl)acetonitrile Chemical compound CC1=CC=CC=C1CC#N WMGVPDQNPUQRND-UHFFFAOYSA-N 0.000 description 4
- DOYSIZKQWJYULQ-UHFFFAOYSA-N 1,1,2,2,2-pentafluoro-n-(1,1,2,2,2-pentafluoroethylsulfonyl)ethanesulfonamide Chemical compound FC(F)(F)C(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)C(F)(F)F DOYSIZKQWJYULQ-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- XGMDYIYCKWMWLY-UHFFFAOYSA-N 2,2,2-trifluoroethanesulfonic acid Chemical compound OS(=O)(=O)CC(F)(F)F XGMDYIYCKWMWLY-UHFFFAOYSA-N 0.000 description 4
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 4
- MRYVOZKBWHWSRJ-UHFFFAOYSA-N 4-(1-adamantyl)-1,1-difluoro-3,4-dioxo-2-(trifluoromethyl)butane-1-sulfonic acid Chemical compound C1C2CC3CC1CC(C2)(C3)C(=O)C(=O)C(C(F)(F)F)C(F)(F)S(=O)(=O)O MRYVOZKBWHWSRJ-UHFFFAOYSA-N 0.000 description 4
- RLTPXEAFDJVHSN-UHFFFAOYSA-M 4-(trifluoromethyl)benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 RLTPXEAFDJVHSN-UHFFFAOYSA-M 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 125000004864 4-thiomethylphenyl group Chemical group 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 235000021357 Behenic acid Nutrition 0.000 description 4
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- UODMSBYDFUPQHC-UHFFFAOYSA-M magnesium;di(propan-2-yl)azanide;bromide Chemical compound CC(C)N([Mg]Br)C(C)C UODMSBYDFUPQHC-UHFFFAOYSA-M 0.000 description 1
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- JXPBRQHHMIKAPW-UHFFFAOYSA-N tris[4-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]phenyl]sulfanium Chemical compound C1=CC(OCC(=O)OC(C)(C)C)=CC=C1[S+](C=1C=CC(OCC(=O)OC(C)(C)C)=CC=1)C1=CC=C(OCC(=O)OC(C)(C)C)C=C1 JXPBRQHHMIKAPW-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Steroid Compounds (AREA)
Description
(式中、R4はそれぞれ独立に水素原子、炭素数1〜10の直鎖状、分岐状又は環状のアルキル基、炭素数6〜15のアリール基、又は炭素数7〜15のアラルキル基を表す。R5は水素原子又はメチル基を表す。R6は炭素数21〜49の水酸基、カルボニル基、エステル基、エーテル基、シアノ基又はアセタール基を含んでもよいアルキル基を表す。R7は単結合、又はメチレン基、酸素原子又は硫黄原子を表す。R8は炭素数1〜9の直鎖状又は分岐状のアルキレン基を表す。R9は炭素数22〜50の水酸基、カルボニル基、エステル基、エーテル基又はシアノ基を含んでもよいアルキル基を表す。)
更に、本発明は、下記一般式(2’)〜(10’)で表される含窒素へテロ環及びステロイド骨格を有する含窒素有機化合物を提供する。
(式中、R4はそれぞれ独立に水素原子、炭素数1〜10の直鎖状、分岐状又は環状のアルキル基、炭素数6〜15のアリール基、又は炭素数7〜15のアラルキル基を表す。R5は水素原子又はメチル基を表す。R6'はステロイド骨格を有する炭素数21〜49の水酸基、カルボニル基、エステル基、エーテル基、シアノ基又はアセタール基を含んでもよいアルキル基を表す。R7は単結合、又はメチレン基、酸素原子又は硫黄原子を表す。R8は炭素数1〜9の直鎖状又は分岐状のアルキレン基を表す。R9'はステロイド骨格を有する炭素数22〜50の水酸基、カルボニル基、エステル基、エーテル基又はシアノ基を含んでもよいアルキル基を表す。)
本発明者らは、化学増幅型レジスト材料への配合により、高い解像性と良好なマスク被覆率依存性を与える化合物について鋭意検討を重ねた。その結果、下記一般式(1)で表される含窒素へテロ環を有する分子量380以上の含窒素有機化合物、好ましくは、下記一般式(2)〜(10)で表される含窒素へテロ環を有する分子量430以上の含窒素有機化合物、更により好ましくは、下記一般式(2’)〜(10’)で表される含窒素へテロ環を有する分子量430以上のステロイド骨格を有する含窒素有機化合物を配合して用いれば、高い解像性と良好なマスク被覆率依存性を与える化学増幅型フォトレジスト材料が得られることを見出し、本発明を完成させたものである。更に本発明のレジスト材料は、水液浸時の水へのアミン化合物の溶出が少ないため、液浸露光にも好適に用いることができる。
(式中、R4はそれぞれ独立に水素原子、炭素数1〜10の直鎖状、分岐状又は環状のアルキル基、炭素数6〜15のアリール基、又は炭素数7〜15のアラルキル基を表す。R5は水素原子又はメチル基を表す。R6は炭素数21〜49の水酸基、カルボニル基、エステル基、エーテル基、シアノ基又はアセタール基を含んでもよいアルキル基を表す。R7は単結合、又はメチレン基、酸素原子又は硫黄原子を表す。R8は炭素数1〜9の直鎖状又は分岐状のアルキレン基を表す。R9は炭素数22〜50の水酸基、カルボニル基、エステル基、エーテル基又はシアノ基を含んでもよいアルキル基を表す。)
一般式(2)〜(7)中、R6は炭素数21〜49の水酸基、カルボニル基、エステル基、エーテル基、シアノ基又はアセタール基を含んでもよいアルキル基を表し、具体的には、後述のR6'の具体例に加え、下記のものを例示できる。下記式中、破線は結合位置を示し、以下同様である。
(式中、R4はそれぞれ独立に水素原子、炭素数1〜10の直鎖状、分岐状又は環状のアルキル基、炭素数6〜15のアリール基、又は炭素数7〜15のアラルキル基を表す。R5は水素原子又はメチル基を表す。R6'はステロイド骨格を有する炭素数21〜49の水酸基、カルボニル基、エステル基、エーテル基、シアノ基又はアセタール基を含んでもよいアルキル基を表す。R7は単結合、又はメチレン基、酸素原子又は硫黄原子を表す。R8は炭素数1〜9の直鎖状又は分岐状のアルキレン基を表す。R9'はステロイド骨格を有する炭素数22〜50の水酸基、カルボニル基、エステル基、エーテル基又はシアノ基を含んでもよいアルキル基を表す。)
一般式(2’)〜(7’)中、R6'はステロイド骨格を有する炭素数21〜49の水酸基、カルボニル基、エステル基、エーテル基、シアノ基又はアセタール基を含んでもよいアルキル基を表し、具体的には下記の構造を例示できるが、これらに限定されない。下記式中、Acはアセチル基を示し、以下同様である。
(式中、R1は両端で結合する窒素原子と共に含窒素へテロ脂肪族環又は含窒素ヘテロ芳香族環を形成する炭素数2〜20の直鎖状、分岐状又は環状の2価の置換基を表し、酸素原子、窒素原子、硫黄原子又はハロゲン原子を含んでもよい。R2は炭素数2〜10のカルボニル基を含んでもよい直鎖状又は分岐状のアルキレン基を表す。R3は炭素数22〜50の水酸基、カルボニル基、エステル基、エーテル基又はシアノ基を含んでもよいアルキル基又はアシル基を表す。Xはハロゲン原子、p−トルエンスルホニルオキシ基、メタンスルホニルオキシ基、トリフルオロメタンスルホニルオキシ基、水酸基などの脱離基を表す。)
(式中、R1は両端で結合する窒素原子と共に含窒素へテロ脂肪族環又は含窒素ヘテロ芳香族環を形成する炭素数2〜20の直鎖状、分岐状又は環状の2価の置換基を表し、酸素原子、窒素原子、硫黄原子又はハロゲン原子を含んでもよい。R2は炭素数2〜10のカルボニル基を含んでもよい直鎖状又は分岐状のアルキレン基を表す。R3は炭素数22〜50の水酸基、カルボニル基、エステル基、エーテル基又はシアノ基を含んでもよいアルキル基又はアシル基を表す。Yはハロゲン原子、アルキル又はアリールスルホニルオキシ基、水酸基、アシルオキシ基、フェノキシ基、アルコキシ基などの脱離基を表す。)
(A)上記式(1)〜(10)及び(2’)〜(10’)で示される含窒素有機化合物、
(B)有機溶剤、
(C)酸不安定基で保護された酸性官能基を有するアルカリ不溶性又は難溶性の樹脂であって、該酸不安定基が脱保護されたときにアルカリ可溶性となるベース樹脂、
(D)酸発生剤
更に、必要に応じて
(E)溶解制御剤
を含有する。
このような有機溶剤としては、例えば、シクロヘキサノン、メチルアミルケトン等のケトン類、3−メトキシブタノール、3−メチル−3−メトキシブタノール、1−メトキシ−2−プロパノール、1−エトキシ−2−プロパノール等のアルコール類、プロピ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メチルエーテル、プロピ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エチルエーテル、プロピレングリコールジメチルエーテル、ジエチレングリコールジメチルエーテル等のエーテル類、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、乳酸エチル、ピルビン酸エチル、酢酸ブチル、3−メトキシプロピオン酸メチル、3−エトキシプロピオン酸エチル、酢酸tert−ブチル、プロピオン酸tert−ブチル、プロピレングリコールモノtert−ブチルエーテルアセテート等のエステル類、γ−ブチロラクトン等のラクトン類が挙げられ、これらの1種を単独で又は2種以上を混合して使用することができるが、これらに限定されるものではない。本発明では、これらの有機溶剤の中でもレジスト成分中の酸発生剤の溶解性が最も優れているジエチレングリコールジメチルエーテルや1−エトキシ−2−プロパノール、プロピレングリコールモノメチルエーテルアセテート及びその混合溶剤が好ましく使用される。有機溶剤の使用量は、ベース樹脂100部に対して200〜1,000部、特に400〜800部が好適である。
(上記式中、R401は置換又は非置換の炭素数1〜10のハロアルキルスルホニル又はハロベンゼンスルホニル基を表す。R402は炭素数1〜11のハロアルキル基を表す。Ar401は置換又は非置換の芳香族基又はヘテロ芳香族基を表す。)
(但し、式中R201、R202はそれぞれ水素原子、又は炭素数1〜8の直鎖状又は分岐状のアルキル基又はアルケニル基を示す。R203は水素原子、又は炭素数1〜8の直鎖状又は分岐状のアルキル基又はアルケニル基、あるいは−(R207)hCOOHを示す。R204は−(CH2)i−(i=2〜10)、炭素数6〜10のアリーレン基、カルボニル基、スルホニル基、酸素原子又は硫黄原子を示す。R205は炭素数1〜10のアルキレン基、炭素数6〜10のアリーレン基、カルボニル基、スルホニル基、酸素原子又は硫黄原子を示す。R206は水素原子、炭素数1〜8の直鎖状又は分岐状のアルキル基、アルケニル基又はそれぞれ水酸基で置換されたフェニル基又はナフチル基を示す。R207は炭素数1〜10の直鎖状又は分岐状のアルキレン基を示す。R208は水素原子又は水酸基を示す。jは0〜5の整数である。u、hは0又は1である。s、t、s’、t’、s’’、t’’はそれぞれs+t=8、s’+t’=5、s’’+t’’=4を満足し、かつ各フェニル骨格中に少なくとも1つの水酸基を有するような数である。αは式(D8)、(D9)の化合物の分子量を100〜1,000とする数である。
(A)上記式(1)〜(10)及び(2’)〜(10’)で示される含窒素有機化合物、
(B)有機溶剤、
(C’)アルカリ可溶性樹脂であって、架橋剤による架橋によってアルカリ難溶性となるベース樹脂、
(D)酸発生剤、
(F)酸によって架橋する架橋剤
を含有する。
本発明の含窒素有機化合物を以下に示す方法で合成した。
[合成例1]ベヘン酸[2−(1H−イミダゾール−1−イル)−1−メチルエチル](quencher 1)の合成
1−(1H−イミダゾール−1−イル)−2−プロパノール(15)12.6g、ジメチルホルムアミド50gの混合物に氷冷、撹拌下、ベヘン酸クロリド(16)35.9gを添加し、その後、室温で2時間撹拌した。トルエン添加、中和に続き、通常の水系後処理(aqueous work−up)を行った後、カラムクロマトグラフィーにより精製を行い、41.3gのベヘン酸[2−(1H−イミダゾール−1−イル)−1−メチルエチル](quencher 1)を得た(収率92%)。
ベヘン酸メチル35.5g(18)、2−モルホリノエタノール19.7g(17)、ナトリウムメトキシド270mg、トルエン150gの混合物を、反応により生成するメタノールを留去しながら6時間加熱還流した。冷却後、通常の水系後処理(aqueous work−up)を行った後、トルエンを留去し、ベヘン酸(2−モルホリノエチル)(quencher 2)41.3gを得た(収率91%)。
IR(KBr):ν=2917,2850,1739,1467,1172,1116cm-1
1H−NMR(600MHz in CDCl3):δ=0.85(3H,t,J=7.1Hz),1.20−1.35(36H,m),1.59(2H,tt,J=7.6,7.3Hz),2.28(2H,t,J=7.6),2.50(4H,m),2.61(2H,br.t,J=5.9Hz),3.69(4H,br.t,J=4.5Hz),4.19(2H,br.t,J=5.9Hz).
2−(1H−ベンズイミダゾール−1−イル)エタノール(19)16.2gとジメチルホルムアミド100gの混合物に、氷冷、撹拌下、デヒドロコール酸クロリド(20)42.1gを加え、その後、室温で2時間撹拌した。酢酸エチルを加えて通常の水系後処理(aqueous work−up)を行った後、カラムクロマトグラフィーにより精製を行い、46.5gのデヒドロコール酸[2−(1H−ベンズイミダゾール−1−イル)エチル](quencher 3)を得た(収率85%)。
コール酸トリホルマート(22)49.3g、シュウ酸クロリド12.7g、トルエン500gの混合物を50℃で3時間撹拌後、氷冷し、2−モルホリノエタノール(21)28.9gを滴下、その後、室温で3時間撹拌した。通常の水系後処理(aqueous work−up)の後、シリカゲルカラムクロマトグラフィーにより精製を行い、コール酸トリホルマート(2−モルホリノエチル)エステル(quencher 4)43.0gを得た(収率71%)。
IR(KBr):ν=2954,2869,2811,1718,1467,1452,1380,1299,1180,1116cm-1
1H−NMR(600MHz in CDCl3):δ=0.74(3H,s),0.83(3H,d,J=6.9Hz),0.93(3H,s),1.05−1.15(2H,m),1.20−1.50(5H,m),1.50−1.60(2H,m),1.60−1.80(9H,m),1.80−1.95(2H,m),2.01(1H,m),2.05−2.15(2H,m),2.20(1H,ddd,J=15.8,9.3,6.5Hz),2.48(4H,m),2.60(2H,t,J=5.9Hz),3.69(4H,br.t,J=4.7Hz),4.18(2H,t,J=5.9Hz),4.70(1H,m),5.06(1H,m),5.23(1H,m),8.01(1H,s),8.09(1H,s),8.15(1H,s).
2−(1H−イミダゾール−1−イル)エタノール(23)11.2g、t−ブトキシカリウム11.2g、テトラヒドロフラン100gの混合物に、氷冷下、クロロメチルコレスタニルエーテル(24)43.7gを加え、その後室温で10時間撹拌した。通常の水系後処理(aqueous work−up)の後、シリカゲルカラムクロマトグラフィーにより精製を行い、1−[2−(コレスタニルオキシメトキシ)エチル]イミダゾール(quencher 5)38.5gを得た(収率75%)。
2−フェニルベンズイミダゾール(25)19.4gとクロロ酢酸コレステリル(26)46.3g、ジメチルホルムアミド200gの混合物を100℃で10時間加熱撹拌した。冷却、中和に続き、通常の水系後処理(aqueous work−up)を行った後、シリカゲルカラムクロマトグラフィーにより精製を行い、2−(2−フェニル−1H−ベンズイミダゾール−1−イル)酢酸コレステリルエステル(quencher 6)51.1gを得た(収率82%)。
サルササポゲニンアクリラート(28)47.1gとテトラヒドロフラン200gの混合物にチオモルホリン(27)10.3gを滴下し、室温で3時間撹拌した。テトラヒドロフランを留去後、シリカゲルカラムクロマトグラフィーにより精製し、サルササポゲニン[3−(チオモルホリノ)プロピオナート](quencher 7)56.2gを得た(収率98%)。
本発明の含窒素有機化合物を配合したレジスト材料を調製し、次いで本発明のパターン形成方法を実施し、その解像性、マスク被覆率依存性、及びパターン上異物の評価を行った。
なお、下記実施例及び比較例で使用したベースポリマー、酸発生剤、クエンチャーの構造式を以下に示す。下記例でMw、Mnはゲル浸透クロマトグラフィー(GPC)により測定したポリスチレン換算の値である。
合成例1で得られた含窒素有機化合物(quencher 1)を用いて、以下に示す組成で混合した後、孔径0.2μmのテフロン(登録商標)フィルターを用いて濾過し、レジスト材料を調製した。
(A)ベースポリマー(Polymer 1)100質量部
(B)酸発生剤(PAG 1)2.0質量部
(C)溶剤としてプロピレングリコールモノメチルエーテルアセテート280質量部及び乳酸エチル120質量部
(D)クエンチャー(quencher 1)0.13質量部
実施例1に準じて、合成例2〜7で合成した含窒素有機化合物(quencher 2〜7)及び比較となる含窒素有機化合物(quencher 8〜10)について、それぞれこれらをクエンチャーとして配合したレジスト材料を調製し(該実施例及び比較例のアミンについて、quencher 1の0.13質量部と等モルを配合)、パターン形成を行った。
(1)解像性評価
現像済みウエハーを上空SEM(走査型電子顕微鏡)により観察し、明領域(bright field、低マスク被覆率の領域)にて、180nmの1:1密集ライン・アンド・スペース・パターンを解像する露光量(最適露光量)において、150nmの1:1密集ライン・アンド・スペース・パターンを剥がれなく分離解像しているかどうかを解像性の指標とした。
(2)マスク被覆率依存性の評価
現像済みウエハーを上空SEM(走査型電子顕微鏡)により観察して、明領域(bright field、低マスク被覆率の領域)にて、180nmの1:1密集ライン・アンド・スペース・パターンを解像する露光量(最適露光量)において、暗領域(dark field、高マスク被覆率の領域)での、180nmの1:1密集ライン・アンド・スペース・パターンのパターン形状を断面SEM(走査型電子顕微鏡)により観察し、マスク被覆率依存性の指標(矩形であれば良好、T−トップならば不良)とした。
(3)パターン上異物の評価
現像済みウエハーを上空SEM(走査型電子顕微鏡)により観察し、目視でのパターン上異物の有無を評価した。
実施例1〜7及び比較例1〜3のレジスト材料について、上記解像性、マスク被覆率依存性、及びパターン上異物の評価を行った。
上記評価結果をもとに、1:1ライン・アンド・スペース・パターンにおける150nm解像性、マスク被覆率依存性(暗領域パターン形状)、及びパターン上異物について下記の表1にまとめた。
合成例1で得られた含窒素有機化合物を用いて、以下に示す組成で混合した後、孔径0.2μmのテフロン(登録商標)フィルターを用いて濾過し、レジスト材料を調製した。
(A)ベースポリマー(Polymer 2)80質量部
(B)酸発生剤(PAG 2)2.0質量部
(C)溶剤としてプロピレングリコールモノメチルエーテルアセテート640質量部
(D)クエンチャー(quencher 1)0.33質量部
このレジスト材料を、反射防止膜(日産化学工業(株)製ARC29A,78nm)を塗布したシリコンウエハー上へ回転塗布し、120℃で60秒間の熱処理を施して、厚さ300nmのレジスト膜を形成した。これをArFエキシマレーザーステッパー((株)ニコン製、NSR−S305B、NA=0.68、σ=0.85、2/3輪帯照明)を用いて露光し、120℃で60秒間の熱処理を施した後、23℃まで冷却し、2.38質量%のテトラメチルアンモニウムヒドロキシド水溶液を用いて、23℃で60秒間パドル現像を行い、1:1のライン・アンド・スペース・パターンを形成した。現像済ウエハーを上空SEMで観察し、0.12μmのライン・アンド・スペース・パターンを1:1で解像する露光量(最適露光量)において、0.10μmのライン・アンド・スペース・パターンを剥がれなく、分離・解像していた。
実施例8に準じて、合成例2〜7で合成した含窒素有機化合物(quencher 2〜7)及び比較となる含窒素有機化合物(quencher 8〜10)について、それぞれこれらをクエンチャーとして配合したレジスト材料を調製し(該実施例及び比較例のアミンについて、quencher 1の0.33質量部と等モルを配合)、パターン形成を行った。
(1)解像性評価
現像済みウエハーを上空SEM(走査型電子顕微鏡)により観察し、明領域(bright field、低マスク被覆率の領域)にて、120nmの1:1密集ライン・アンド・スペース・パターンを解像する露光量(最適露光量)において、100nmの1:1密集ライン・アンド・スペース・パターンを剥がれなく分離解像しているかどうかを解像性の指標とした。
(2)マスク被覆率依存性の評価
現像済みウエハーを上空SEM(走査型電子顕微鏡)により観察して、明領域(bright field、低マスク被覆率の領域)にて、120nmの1:1密集ライン・アンド・スペース・パターンを解像する露光量(最適露光量)において、暗領域(dark field、高マスク被覆率の領域)での、120nmの1:1密集ライン・アンド・スペース・パターンのパターン形状を断面SEM(走査型電子顕微鏡)により観察し、マスク被覆率依存性の指標(矩形であれば良好、T−トップならば不良)とした。
(3)パターン上異物の評価
現像済みウエハーを上空SEM(走査型電子顕微鏡)により観察し、目視でのパターン上異物の有無を評価した。
実施例8〜14及び比較例4〜6のレジスト材料について、上記解像性、マスク被覆率依存性、及びパターン上異物の評価を行った。
上記評価結果をもとに、1:1ライン・アンド・スペース・パターンにおける100nm解像性、マスク被覆率依存性(暗領域パターン形状)、及びパターン上異物について下記の表2にまとめた。
Claims (2)
- 下記一般式(2)〜(10)で表される含窒素へテロ環を有する含窒素有機化合物。
(式中、R4はそれぞれ独立に水素原子、炭素数1〜10の直鎖状、分岐状又は環状のアルキル基、炭素数6〜15のアリール基、又は炭素数7〜15のアラルキル基を表す。R5は水素原子又はメチル基を表す。R6は炭素数21〜49の水酸基、カルボニル基、エステル基、エーテル基、シアノ基又はアセタール基を含んでもよいアルキル基を表す。R7は単結合、又はメチレン基、酸素原子又は硫黄原子を表す。R8は炭素数1〜9の直鎖状又は分岐状のアルキレン基を表す。R9は炭素数22〜50の水酸基、カルボニル基、エステル基、エーテル基又はシアノ基を含んでもよいアルキル基を表す。) - 下記一般式(2’)〜(10’)で表される含窒素へテロ環及びステロイド骨格を有する含窒素有機化合物。
(式中、R4はそれぞれ独立に水素原子、炭素数1〜10の直鎖状、分岐状又は環状のアルキル基、炭素数6〜15のアリール基、又は炭素数7〜15のアラルキル基を表す。R5は水素原子又はメチル基を表す。R6'はステロイド骨格を有する炭素数21〜49の水酸基、カルボニル基、エステル基、エーテル基、シアノ基又はアセタール基を含んでもよいアルキル基を表す。R7は単結合、又はメチレン基、酸素原子又は硫黄原子を表す。R8は炭素数1〜9の直鎖状又は分岐状のアルキレン基を表す。R9'はステロイド骨格を有する炭素数22〜50の水酸基、カルボニル基、エステル基、エーテル基又はシアノ基を含んでもよいアルキル基を表す。)
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