JP5304648B2 - Radiation sensitive compositions and compounds - Google Patents
Radiation sensitive compositions and compounds Download PDFInfo
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- JP5304648B2 JP5304648B2 JP2009529061A JP2009529061A JP5304648B2 JP 5304648 B2 JP5304648 B2 JP 5304648B2 JP 2009529061 A JP2009529061 A JP 2009529061A JP 2009529061 A JP2009529061 A JP 2009529061A JP 5304648 B2 JP5304648 B2 JP 5304648B2
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 84
- 230000005855 radiation Effects 0.000 title claims description 71
- 239000000203 mixture Substances 0.000 title claims description 61
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
- -1 2-methyl-2-adamantyl group Chemical group 0.000 claims description 80
- 239000002253 acid Substances 0.000 claims description 61
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 238000009792 diffusion process Methods 0.000 claims description 16
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 abstract description 16
- 239000002904 solvent Substances 0.000 description 32
- 230000035945 sensitivity Effects 0.000 description 20
- 239000010408 film Substances 0.000 description 18
- 238000010894 electron beam technology Methods 0.000 description 16
- 239000000654 additive Substances 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000005530 etching Methods 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000002723 alicyclic group Chemical group 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 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 8
- SMEROWZSTRWXGI-UHFFFAOYSA-N Lithocholsaeure Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 SMEROWZSTRWXGI-UHFFFAOYSA-N 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- 239000002243 precursor Substances 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000007514 bases Chemical class 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 6
- 229960003964 deoxycholic acid Drugs 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000001459 lithography Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 5
- VTJUKNSKBAOEHE-UHFFFAOYSA-N calixarene Chemical compound COC(=O)COC1=C(CC=2C(=C(CC=3C(=C(C4)C=C(C=3)C(C)(C)C)OCC(=O)OC)C=C(C=2)C(C)(C)C)OCC(=O)OC)C=C(C(C)(C)C)C=C1CC1=C(OCC(=O)OC)C4=CC(C(C)(C)C)=C1 VTJUKNSKBAOEHE-UHFFFAOYSA-N 0.000 description 5
- 238000013329 compounding Methods 0.000 description 5
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- 239000002274 desiccant Substances 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 230000018109 developmental process Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910003472 fullerene Inorganic materials 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 238000001226 reprecipitation Methods 0.000 description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- 239000012953 triphenylsulfonium Substances 0.000 description 4
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical class C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- YCMDNBGUNDHOOD-UHFFFAOYSA-N n -((trifluoromethylsulfonyl)oxy)-5-norbornene-2,3-dicarboximide Chemical compound C1=CC2CC1C1C2C(=O)N(OS(=O)(=O)C(F)(F)F)C1=O YCMDNBGUNDHOOD-UHFFFAOYSA-N 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 238000005406 washing Methods 0.000 description 3
- JYVXNLLUYHCIIH-UHFFFAOYSA-N (+/-)-mevalonolactone Natural products CC1(O)CCOC(=O)C1 JYVXNLLUYHCIIH-UHFFFAOYSA-N 0.000 description 2
- SGYQZOQILXLBIB-UHFFFAOYSA-M (4-fluorophenyl)-diphenylsulfanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(F)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 SGYQZOQILXLBIB-UHFFFAOYSA-M 0.000 description 2
- RPLQAZMQMJTROY-UHFFFAOYSA-M (4-fluorophenyl)-phenyliodanium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound C1=CC(F)=CC=C1[I+]C1=CC=CC=C1.[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RPLQAZMQMJTROY-UHFFFAOYSA-M 0.000 description 2
- JHIGBMVXTRJDTO-UHFFFAOYSA-N (4-hydroxyphenyl)-diphenylsulfanium;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.C1=CC(O)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 JHIGBMVXTRJDTO-UHFFFAOYSA-N 0.000 description 2
- ADOBQGXDCURFNZ-UHFFFAOYSA-N (4-hydroxyphenyl)-diphenylsulfanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(O)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 ADOBQGXDCURFNZ-UHFFFAOYSA-N 0.000 description 2
- YTQJRXUPPRAIEP-UHFFFAOYSA-M (7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonate;(4-fluorophenyl)-phenyliodanium Chemical compound C1=CC(F)=CC=C1[I+]C1=CC=CC=C1.C1CC2(CS([O-])(=O)=O)C(=O)CC1C2(C)C YTQJRXUPPRAIEP-UHFFFAOYSA-M 0.000 description 2
- HHYVKZVPYXHHCG-UHFFFAOYSA-M (7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonate;diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1.C1CC2(CS([O-])(=O)=O)C(=O)CC1C2(C)C HHYVKZVPYXHHCG-UHFFFAOYSA-M 0.000 description 2
- FJALTVCJBKZXKY-UHFFFAOYSA-M (7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonate;triphenylsulfanium Chemical compound C1CC2(CS([O-])(=O)=O)C(=O)CC1C2(C)C.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FJALTVCJBKZXKY-UHFFFAOYSA-M 0.000 description 2
- VLLPVDKADBYKLM-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate;triphenylsulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 VLLPVDKADBYKLM-UHFFFAOYSA-M 0.000 description 2
- CEOJVJLIGTZVND-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate;tris(4-methoxyphenyl)sulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F.C1=CC(OC)=CC=C1[S+](C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 CEOJVJLIGTZVND-UHFFFAOYSA-M 0.000 description 2
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 2
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
- DMFAHCVITRDZQB-UHFFFAOYSA-N 1-propoxypropan-2-yl acetate Chemical compound CCCOCC(C)OC(C)=O DMFAHCVITRDZQB-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- IKMBXKGUMLSBOT-UHFFFAOYSA-N 2,3,4,5,6-pentafluorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=C(F)C(F)=C(F)C(F)=C1F IKMBXKGUMLSBOT-UHFFFAOYSA-N 0.000 description 2
- ZCIVTTVWBMTBTH-UHFFFAOYSA-M 2,4-difluorobenzenesulfonate;diphenyl-(2,4,6-trimethylphenyl)sulfanium Chemical compound [O-]S(=O)(=O)C1=CC=C(F)C=C1F.CC1=CC(C)=CC(C)=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 ZCIVTTVWBMTBTH-UHFFFAOYSA-M 0.000 description 2
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 2
- AILVYPLQKCQNJC-UHFFFAOYSA-N 2,6-dimethylcyclohexan-1-one Chemical compound CC1CCCC(C)C1=O AILVYPLQKCQNJC-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- VLSXSDQKIHYGKU-UHFFFAOYSA-N 2-[5-(2,5-dioxopyrrolidin-1-yl)oxysulfonyl-2-methyl-2-bicyclo[2.2.1]heptanyl]acetic acid Chemical compound OC(=O)CC1(C)CC2CC1CC2S(=O)(=O)ON1C(=O)CCC1=O VLSXSDQKIHYGKU-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- JFUOAGBSDGCVES-UHFFFAOYSA-N 3-but-2-enyl-4-methylpyrrolidine-2,5-dione Chemical compound CC=CCC1C(C)C(=O)NC1=O JFUOAGBSDGCVES-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- AOKRXIIIYJGNNU-UHFFFAOYSA-N 3-methylcyclopentan-1-one Chemical compound CC1CCC(=O)C1 AOKRXIIIYJGNNU-UHFFFAOYSA-N 0.000 description 2
- JVZRCNQLWOELDU-UHFFFAOYSA-N 4-Phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 2
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
- VIQXDCYEJAOMDP-UHFFFAOYSA-N piperazine pyrazine Chemical compound C1CNCCN1.C1=CN=CC=N1 VIQXDCYEJAOMDP-UHFFFAOYSA-N 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 229920000083 poly(allylamine) Polymers 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- PMZDQRJGMBOQBF-UHFFFAOYSA-N quinolin-4-ol Chemical compound C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical compound C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229940081623 rose bengal Drugs 0.000 description 1
- 229930187593 rose bengal Natural products 0.000 description 1
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000005469 synchrotron radiation Effects 0.000 description 1
- 229940066769 systemic antihistamines substituted alkylamines Drugs 0.000 description 1
- BFFLLBPMZCIGRM-MRVPVSSYSA-N tert-butyl (2r)-2-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@@H]1CO BFFLLBPMZCIGRM-MRVPVSSYSA-N 0.000 description 1
- BFFLLBPMZCIGRM-QMMMGPOBSA-N tert-butyl (2s)-2-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1CO BFFLLBPMZCIGRM-QMMMGPOBSA-N 0.000 description 1
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
- VKUZRUNYENZANE-UHFFFAOYSA-N tert-butyl n-(1-adamantyl)-n-[(2-methylpropan-2-yl)oxycarbonyl]carbamate Chemical compound C1C(C2)CC3CC2CC1(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C3 VKUZRUNYENZANE-UHFFFAOYSA-N 0.000 description 1
- WFLZPBIWJSIELX-UHFFFAOYSA-N tert-butyl n-[10-[(2-methylpropan-2-yl)oxycarbonylamino]decyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCCCCCCCCNC(=O)OC(C)(C)C WFLZPBIWJSIELX-UHFFFAOYSA-N 0.000 description 1
- HXINNZFJKZMJJJ-UHFFFAOYSA-N tert-butyl n-[12-[(2-methylpropan-2-yl)oxycarbonylamino]dodecyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCCCCCCCCCCNC(=O)OC(C)(C)C HXINNZFJKZMJJJ-UHFFFAOYSA-N 0.000 description 1
- VDSMPNIBLRKWEG-UHFFFAOYSA-N tert-butyl n-[6-[(2-methylpropan-2-yl)oxycarbonylamino]hexyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCCCCNC(=O)OC(C)(C)C VDSMPNIBLRKWEG-UHFFFAOYSA-N 0.000 description 1
- NMEQKHOJGXGOIL-UHFFFAOYSA-N tert-butyl n-[7-[(2-methylpropan-2-yl)oxycarbonylamino]heptyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCCCCCNC(=O)OC(C)(C)C NMEQKHOJGXGOIL-UHFFFAOYSA-N 0.000 description 1
- YLKUQZHLQVRJEV-UHFFFAOYSA-N tert-butyl n-[8-[(2-methylpropan-2-yl)oxycarbonylamino]octyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCCCCCCNC(=O)OC(C)(C)C YLKUQZHLQVRJEV-UHFFFAOYSA-N 0.000 description 1
- XSIWKTQGPJNJBV-UHFFFAOYSA-N tert-butyl n-[9-[(2-methylpropan-2-yl)oxycarbonylamino]nonyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCCCCCCCNC(=O)OC(C)(C)C XSIWKTQGPJNJBV-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- IZBIRHQNPWSIET-UHFFFAOYSA-M trifluoromethanesulfonate;tris(4-fluorophenyl)sulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(F)=CC=C1[S+](C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 IZBIRHQNPWSIET-UHFFFAOYSA-M 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- WUKMCKCDYKBLBG-UHFFFAOYSA-N tris(4-methoxyphenyl)sulfanium Chemical compound C1=CC(OC)=CC=C1[S+](C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 WUKMCKCDYKBLBG-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
-
- 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/92—Systems containing at least three condensed rings with a condensed ring system consisting of at least two mutually uncondensed aromatic ring systems, linked by an annular structure formed by carbon chains on non-adjacent positions of the aromatic system, e.g. cyclophanes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Materials For Photolithography (AREA)
Abstract
Description
本発明は、感放射線性組成物および化合物に関し、更に詳しくは、特に電子線(以下、「EB」と記す場合がある)または極紫外線(以下、「EUV」と記す場合がある)による微細パターン形成に好適なポジ型の感放射線性組成物および当該感放射線性組成物を得ることができる化合物に関する。 The present invention relates to a radiation-sensitive composition and a compound, and more particularly, a fine pattern by an electron beam (hereinafter sometimes referred to as “EB”) or extreme ultraviolet rays (hereinafter sometimes referred to as “EUV”). The present invention relates to a positive-type radiation-sensitive composition suitable for formation and a compound capable of obtaining the radiation-sensitive composition.
集積回路素子の製造に代表される微細加工の分野においては、集積回路のより高い集積度を得るために、リソグラフィーにおけるデザインルールの微細化が急速に進行しており、微細加工を安定して行うことができるリソグラフィープロセスの開発が強く推し進められている。 In the field of microfabrication represented by the manufacture of integrated circuit elements, in order to obtain a higher degree of integration of integrated circuits, miniaturization of design rules in lithography is progressing rapidly, and microfabrication is performed stably. The development of lithographic processes that can do this is strongly promoted.
しかし、従来使用されてきた、例えば、KrF、ArFエキシマレーザーを用いたリソグラフィープロセスでは、微細パターンを高精度に形成することが困難になってきている。そこで、最近では、微細加工を達成するために、KrF、ArFエキシマレーザーに代えて、電子線を使用するリソグラフィープロセスが提案されている。 However, it has become difficult to form a fine pattern with high accuracy by a lithography process using a KrF or ArF excimer laser, for example, which has been conventionally used. Therefore, recently, in order to achieve microfabrication, a lithography process using an electron beam instead of KrF or ArF excimer laser has been proposed.
この電子線を使用したリソグラフィープロセスに用いられる電子線レジスト材料として、例えば、(1)PMMA(ポリメチルメタクリレート)等のメタクリル系主鎖切断型ポジレジスト(例えば、特許文献1,2参照)、(2)酸解離性基で部分的に保護されたポリヒドロキシスチレン系樹脂(KrFエキシマ用樹脂)及びノボラック(i線用樹脂)と酸発生剤とを有する化学増幅型ポジレジスト(例えば、非特許文献1参照)、(3)カリックスアレーン、フラーレン等の薄膜形成能を有する(アモルファス性)有機低分子含有ポジ及びネガ型レジスト(例えば、特許文献3〜11参照)、多価フェノール化合物を用いたレジスト(例えば、特許文献12〜13参照)などが提案されている。また、カリックスアレーン、フラーレン以外の薄膜形成能を有する有機低分子として、1,3,5−トリス[4−(2−t−ブトキシカルボニルオキシ)フェニル]ベンゼンを含有する化学増幅型レジストが提案されている(例えば、非特許文献2参照)。 As an electron beam resist material used in a lithography process using this electron beam, for example, (1) a methacrylic main chain-cut positive resist such as PMMA (polymethyl methacrylate) (see, for example, Patent Documents 1 and 2), ( 2) A chemically amplified positive resist (for example, non-patent document) having a polyhydroxystyrene-based resin (resin for KrF excimer) and a novolak (resin for i-line) partially protected with an acid-dissociable group and an acid generator. 1), (3) (amorphous) organic low-molecule-containing positive and negative resists having a thin film-forming ability such as calixarene and fullerene (for example, see Patent Documents 3 to 11), resists using polyhydric phenol compounds (For example, refer to Patent Documents 12 to 13). In addition, a chemically amplified resist containing 1,3,5-tris [4- (2-t-butoxycarbonyloxy) phenyl] benzene has been proposed as an organic small molecule having a thin film forming ability other than calixarene and fullerene. (For example, refer nonpatent literature 2).
しかしながら、上記電子線レジスト材料のうち、(1)のポジ型レジストはエッチング耐性、感度に問題があり実用化は困難である。例えば、感度を向上させるため、ポリt−ブチルα−クロロメチルスチレンを用いたものや、樹脂末端に電子線により切断され易い原子(N、O、S)を導入したものが提案されているが(特許文献1,2)、感度の一定の改良は認められるが、感度、エッチング耐性ともに実用レベルには至っていない。また、(2)の化学増幅型ポジレジスト(例えば、非特許文献1)は、感度は高いが、樹脂を用いているため、微細なパターン形成時にはナノエッジラフネスが問題となる。ここで、ナノエッジラフネスとは、レジストのパターンと基板界面のエッジが、レジストの特性に起因して、ライン方向と垂直な方向に不規則に変動するために、パターンを真上から見たときにエッジが凹凸に見えることをいう。レジストをマスクとするエッチング工程によりこの凹凸が転写されてしまうために、電気特性が劣化してしまい、歩留りの低下が生ずる。特に、0.15μm以下の超微細領域におけるナノエッジラフネスの改良は、極めて重要な課題となっている。(3)のレジストの中で、カリックスアレーンを用いたレジスト(例えば、特許文献3〜5)は、エッチング耐性に優れるが、構造的に分子間の相互作用が非常に強く、現像液に対する溶解性が悪いため満足なパターンを得ることができない。また、カリックスアレーン誘導体を用いた化合物についての報告(例えば、特許文献6参照)はあるが、ナノエッジラフネスに関する性能は明らかでない。 However, among the electron beam resist materials, the positive resist (1) has problems in etching resistance and sensitivity and is difficult to put into practical use. For example, in order to improve sensitivity, those using poly-t-butyl α-chloromethylstyrene and those having atoms (N, O, S) that are easily cleaved by an electron beam at the resin end have been proposed. (Patent Documents 1 and 2), a certain improvement in sensitivity is recognized, but neither sensitivity nor etching resistance has reached a practical level. Further, the chemical amplification type positive resist (2) (for example, Non-Patent Document 1) has high sensitivity, but uses a resin, so that nano edge roughness becomes a problem when a fine pattern is formed. Here, nano edge roughness means that when the pattern is viewed from directly above, the resist pattern and the edge of the substrate interface vary irregularly in the direction perpendicular to the line direction due to the resist characteristics. It means that the edge looks uneven. Since the unevenness is transferred by the etching process using the resist as a mask, the electrical characteristics are deteriorated and the yield is reduced. In particular, improvement of nano edge roughness in an ultrafine region of 0.15 μm or less is an extremely important issue. Among the resists of (3), resists using calixarene (for example, Patent Documents 3 to 5) are excellent in etching resistance but structurally have very strong intermolecular interaction and solubility in a developer. However, a satisfactory pattern cannot be obtained. In addition, there are reports on compounds using calixarene derivatives (see, for example, Patent Document 6), but performance regarding nanoedge roughness is not clear.
また、フラーレンを用いたレジスト(例えば、特許文献7〜11)は、エッチング耐性については良好であるが、塗布性及び感度が実用レベルに至っていない。また、カリックスアレーン、フラーレン以外の薄膜形成能を有する有機低分子として、1,3,5−トリス[4−(2−t−ブトキシカルボニルオキシ)フェニル]ベンゼンを含有する化学増幅型レジスト(例えば、非特許文献2)は、塗布性、基板との接着性、及び感度において十分ではなく、実用レベルには達していない。更に、多価フェノール化合物を用いたレジスト(例えば、特許文献12〜13)は、解像度については良好であるが、感度は実用レベルに至っていない。 Moreover, although the resist (for example, patent documents 7-11) using fullerene is favorable about etching tolerance, the applicability | paintability and sensitivity have not reached the practical use level. In addition, a chemically amplified resist containing 1,3,5-tris [4- (2-t-butoxycarbonyloxy) phenyl] benzene as an organic small molecule having a thin film forming ability other than calixarene and fullerene (for example, Non-patent document 2) is not sufficient in applicability, adhesion to a substrate, and sensitivity, and has not reached a practical level. Furthermore, resists using polyhydric phenol compounds (for example, Patent Documents 12 to 13) have good resolution, but have not reached a practical level.
本発明は、このような従来技術の有する問題点に鑑みてなされたものであり、その課題とするところは、電子線または極紫外線に有効に感応し、ナノエッジラフネス、エッチング耐性、感度に優れ、微細パターンを高精度にかつ安定して形成することが可能な化学増幅型ポジ型レジスト膜を成膜可能な感放射線性組成物、及びこの感放射線性組成物を得ることができる化合物を提供する。 The present invention has been made in view of such problems of the prior art, and the problem is that it effectively responds to electron beams or extreme ultraviolet rays, and is excellent in nano edge roughness, etching resistance, and sensitivity. Provided are a radiation-sensitive composition capable of forming a chemically amplified positive resist film capable of forming a fine pattern with high accuracy and stability, and a compound capable of obtaining this radiation-sensitive composition To do.
本発明者らは上記課題を達成すべく鋭意検討した結果、所定の構造を有する化合物及びこの化合物と感放射線性酸発生剤とを含有する感放射線性組成物によって、上記課題を達成することが可能であることを見出し、本発明を完成するに至った。 As a result of intensive studies to achieve the above-mentioned problems, the present inventors can achieve the above-described problems with a compound having a predetermined structure and a radiation-sensitive composition containing this compound and a radiation-sensitive acid generator. The inventors have found that this is possible and have completed the present invention.
即ち、本発明によれば、以下に示す、化合物及び感放射線性組成物が提供される。 That is, according to the present invention, the following compounds and radiation-sensitive compositions are provided.
[1] (a)下記一般式(2)で表される化合物と、(b)放射線が照射されることにより酸を発生する感放射線性酸発生剤とを含有する感放射線性組成物。 [1] A radiation-sensitive composition comprising (a) a compound represented by the following general formula ( 2 ) and (b) a radiation-sensitive acid generator that generates an acid when irradiated with radiation.
(一般式(2)において、Rは、それぞれ独立に、水素原子または下記一般式(3−1)で表される基である。ただし、Rの少なくとも一つは下記一般式(3−1)で表される基である。nは0〜30の整数である。)
[2] 前記一般式(3−1)中のR1が、tert−ブチル、2−メチル−2−アダマンチル基、2−エチル−2−アダマンチル基、1−エチルシクロペンチル基、または1−メチルシクロペンチル基でありかつ、mが0または1である上記[1]に記載の感放射線性組成物。 [ 2 ] R 1 in the general formula (3-1) is tert-butyl, 2-methyl-2-adamantyl group, 2-ethyl-2-adamantyl group, 1-ethylcyclopentyl group, or 1-methylcyclopentyl. The radiation-sensitive composition according to [ 1 ], which is a group and m is 0 or 1 .
[3] 前記(b)感放射線性酸発生剤が、オニウム塩、ジアゾメタン化合物、およびスルホンイミド化合物よりなる群から選択される少なくとも一種である上記[2]に記載の感放射線性組成物。 [ 3 ] The radiation-sensitive composition according to [ 2 ], wherein the (b) radiation-sensitive acid generator is at least one selected from the group consisting of an onium salt, a diazomethane compound, and a sulfonimide compound.
[4] (c)酸拡散制御剤を更に含有する上記[1]〜[3]のいずれかに記載の感放射線性組成物。 [ 4 ] The radiation-sensitive composition according to any one of [1] to [ 3 ], further comprising (c) an acid diffusion controller.
[5] 下記一般式(2)で表される化合物。 [ 5 ] A compound represented by the following general formula ( 2 ).
(一般式(2)において、Rは、それぞれ独立に、水素原子または下記一般式(3−1)で表される基である。ただし、Rの少なくとも一つは下記一般式(3−1)で表される基である。nは0〜30の整数である。)
本発明の感放射線性組成物は、電子線または極紫外線に有効に感応し、ナノエッジラフネス、エッチング耐性、感度に優れ、微細パターンを高精度にかつ安定して形成可能な化学増幅型ポジ型レジスト膜を製膜できるという効果を奏するものである。 The radiation-sensitive composition of the present invention is a chemically amplified positive type that is sensitive to electron beams or extreme ultraviolet rays, has excellent nano edge roughness, etching resistance and sensitivity, and can form fine patterns with high accuracy and stability. This produces an effect that a resist film can be formed.
本発明の化合物は、電子線または極紫外線に有効に感応し、ナノエッジラフネス、エッチング耐性、感度に優れ、微細パターンを高精度にかつ安定して形成可能な化学増幅型ポジ型レジスト膜を製膜できる感放射線性組成物を得ることができるという効果を奏するものである。 The compound of the present invention produces a chemically amplified positive resist film that is sensitive to electron beams or extreme ultraviolet rays, has excellent nano edge roughness, etching resistance and sensitivity, and can form fine patterns with high precision and stability. The effect is that a radiation-sensitive composition that can be formed into a film can be obtained.
以下、本発明の実施の最良の形態について説明するが、本発明は以下の実施の形態に限定されるものではなく、本発明の趣旨を逸脱しない範囲で、当業者の通常の知識に基づいて、以下の実施の形態に対し適宜変更、改良等が加えられたものも本発明の範囲に入ることが理解されるべきである。 BEST MODE FOR CARRYING OUT THE INVENTION The best mode for carrying out the present invention will be described below, but the present invention is not limited to the following embodiment, and is based on the ordinary knowledge of those skilled in the art without departing from the gist of the present invention. It should be understood that modifications and improvements as appropriate to the following embodiments also fall within the scope of the present invention.
[1]化合物:
本発明の化合物は、下記一般式(1)で表されるもの(以下「(a)化合物」と記す場合がある)である。この(a)化合物は、ベンゼン環に結合した複数のヒドロキシル基を有し、そのヒドロキシル基の中の少なくとも一つが酸解離性基によって保護された構造を有する酸解離性基含有(修飾)化合物である。従って、(a)化合物は、その酸解離性基が酸により解離し、上記酸解離性基が脱離した後は、アルカリ可溶性となるものである。[1] Compound:
The compound of the present invention is represented by the following general formula (1) (hereinafter sometimes referred to as “(a) compound”). This compound (a) is an acid-dissociable group-containing (modified) compound having a structure in which a plurality of hydroxyl groups bonded to a benzene ring have a structure in which at least one of the hydroxyl groups is protected by an acid-dissociable group. is there. Accordingly, the compound (a) is alkali-soluble after the acid dissociable group is dissociated by the acid and the acid dissociable group is eliminated.
一般式(1)において、Rは、それぞれ独立に、水素原子または1価の酸解離性基である。ただし、Rの少なくとも一つは1価の酸解離性基である。Yは相互に独立に炭素数1〜10の置換もしくは非置換のアルキル基、炭素数2〜10の置換もしくは非置換のアルケニル基、炭素数2〜10の置換もしくは非置換のアルキニル基、炭素数7〜10の置換もしくは非置換のアラルキル基、炭素数1〜10の置換もしくは非置換のアルコキシ基、または置換もしくは非置換のフェノキシ基である。qは相互に独立に0または1である。nは0以上の整数であり、好ましくは0〜30である。 In the general formula (1), each R is independently a hydrogen atom or a monovalent acid dissociable group. However, at least one of R is a monovalent acid dissociable group. Y is independently substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, carbon number A substituted or unsubstituted aralkyl group having 7 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, or a substituted or unsubstituted phenoxy group. q is 0 or 1 independently of each other. n is an integer of 0 or more, preferably 0-30.
その中でも下記一般式(2)で表される構造が好ましい。 Among these, the structure represented by the following general formula (2) is preferable.
一般式(2)において、Rは、それぞれ独立に、水素原子または1価の酸解離性基である。ただし、Rの少なくとも一つは1価の酸解離性基である。nは0以上の整数である。 In the general formula (2), each R is independently a hydrogen atom or a monovalent acid dissociable group. However, at least one of R is a monovalent acid dissociable group. n is an integer of 0 or more.
上記(a)化合物は、例えば、下記方法により製造される前駆体を得た後、この前駆体に、酸解離性基を少なくとも一つ導入することにより得ることができる。 The compound (a) can be obtained, for example, by obtaining a precursor produced by the following method and then introducing at least one acid-dissociable group into the precursor.
まず、上記(a)化合物を製造するための前駆体は、例えば、下記一般式(4)で表される化合物と下記式(5)で表される化合物を溶媒中、触媒の存在下で反応時間12時間〜50時間、反応温度60℃〜90℃の条件で脱水縮合させることにより得ることができる。上記触媒としては、例えば、酸触媒等を挙げることができる。触媒としては、例えば塩酸などを用いることができる。触媒の使用量は、例えばレゾルシノール20mmolと1,4−ブタンジアール6mmolとの反応系において12規定の濃塩酸2.0ミリリットルである。 First, the precursor for producing the compound (a) is, for example, a reaction between a compound represented by the following general formula (4) and a compound represented by the following formula (5) in a solvent in the presence of a catalyst. It can be obtained by dehydrating and condensing at a reaction temperature of 60 ° C. to 90 ° C. for 12 hours to 50 hours. As said catalyst, an acid catalyst etc. can be mentioned, for example. For example, hydrochloric acid or the like can be used as the catalyst. The amount of the catalyst used is, for example, 2.0 ml of 12 N concentrated hydrochloric acid in a reaction system of 20 mmol of resorcinol and 6 mmol of 1,4-butane dial.
なお、上記式(5)で表される化合物は、例えば、下記式(5−1)で表される化合物と水及び酸触媒とを混合することによって得ることができる。そのため、上記(a)化合物は、一般式(4)で表される化合物と下記式(5−1)で表される化合物とを、水及び酸触媒の存在下、60〜90℃で12〜48時間脱水縮合させることにより得ることもできる。 In addition, the compound represented by the said Formula (5) can be obtained by mixing the compound represented by the following formula (5-1), water, and an acid catalyst, for example. Therefore, the compound (a) is a compound represented by the general formula (4) and a compound represented by the following formula (5-1) in the presence of water and an acid catalyst at 60 to 90 ° C. It can also be obtained by dehydration condensation for 48 hours.
なお、上記一般式(4)で表される化合物(以下、「化合物(4)」と記す場合がある)と、上記式(5)で表される化合物(以下、「化合物(5)」と記す場合がある)の混合比に特に制限はないが、収率の観点から、化合物(5)1molに対して、化合物(4)が、20.00〜1.00molの範囲であることが好ましく、15.00〜1.50molの範囲であることが更に好ましく、13.00〜2.00molの範囲であることが特に好ましい。化合物(4)が1.00mol未満であると、目的の化合物の収率が低下するおそれがある。一方、20.00mol超であると、目的の化合物の収率が低下するおそれがある。 The compound represented by the above general formula (4) (hereinafter sometimes referred to as “compound (4)”) and the compound represented by the above formula (5) (hereinafter referred to as “compound (5)”) The mixing ratio is not particularly limited, but from the viewpoint of yield, the compound (4) is preferably in the range of 20.00 to 1.00 mol with respect to 1 mol of the compound (5). The range of 15.00 to 1.50 mol is more preferable, and the range of 13.0 to 2.00 mol is particularly preferable. There exists a possibility that the yield of the target compound may fall that a compound (4) is less than 1.00 mol. On the other hand, if it exceeds 20.00 mol, the yield of the target compound may be reduced.
また、反応溶液中の基質濃度(化合物(4)と化合物(5)の合計の濃度)に特に制限はないが、収率の観点から、0.01mol/L以上であることが好ましく、0.2mol/L以上であることが特に好ましい。モノマー濃度が、0.01mol/L未満であると、目的の化合物の収率が低下するおそれがある。溶媒としては、例えばエタノール、イソプロパノール、n−プロパノールなどを用いることができ、これらの中では、高い収率が得られることから、エタノールが好ましい。 Further, the substrate concentration in the reaction solution (the total concentration of the compound (4) and the compound (5)) is not particularly limited, but is preferably 0.01 mol / L or more from the viewpoint of yield. It is particularly preferably 2 mol / L or more. There exists a possibility that the yield of the target compound may fall that a monomer concentration is less than 0.01 mol / L. As the solvent, for example, ethanol, isopropanol, n-propanol, and the like can be used. Among these, ethanol is preferable because a high yield can be obtained.
溶媒の使用量は、例えばレゾルシノール20mmol、1,4−ブタンジアール6mmolとの反応系において2.0ミリリットルである。 The amount of the solvent used is, for example, 2.0 ml in a reaction system with 20 mmol of resorcinol and 6 mmol of 1,4-butane dial.
次に、上記(a)化合物は、上記前駆体と、例えば、後述する一般式(3−1)または一般式(3−2)で表される基を有する化合物を溶媒中、酸または塩基の存在下で反応時間1時間〜20時間、反応温度−20℃〜100℃の条件で反応させることにより得ることができる。 Next, the compound (a) is obtained by mixing the compound having the precursor and a group represented by the general formula (3-1) or the general formula (3-2) described below with an acid or a base in a solvent. It can be obtained by reacting in the presence of a reaction time of 1 hour to 20 hours and a reaction temperature of -20 ° C to 100 ° C.
なお、上記前駆体と一般式(3−1)または一般式(3−2)で表される基を有する化合物との混合比には特に制限はないが、収率の観点から、上記前駆体のフェノール性水酸基1molに対して、上記一般式(3−1)または一般式(3−2)で表される基を有する化合物が、0.01mol以上であることが好ましく、0.05〜0.80molであることが更に好ましい。上記一般式(3−1)または一般式(3−2)で表される基を有する化合物が0.01mol未満であると、目的の化合物の収率が低下するおそれがある。一方、上記前駆体の水酸基が全て保護されているとナノエッジラフネスが悪化するおそれがある。 The mixing ratio between the precursor and the compound having a group represented by the general formula (3-1) or the general formula (3-2) is not particularly limited, but from the viewpoint of yield, the precursor is used. It is preferable that the compound which has group represented by the said General formula (3-1) or General formula (3-2) with respect to 1 mol of phenolic hydroxyl groups of 0.01 mol or more is 0.05-0. More preferably, it is 80 mol. There exists a possibility that the yield of the target compound may fall that the compound which has group represented by the said general formula (3-1) or general formula (3-2) is less than 0.01 mol. On the other hand, if all the hydroxyl groups of the precursor are protected, the nano edge roughness may be deteriorated.
上記一般式(2)中のRは、それぞれ独立に、水素原子または1価の酸解離性基である。但し、Rは、その少なくとも一つが1価の酸解離性基であることが好ましい。上記酸解離性基はその構造には特に制限はないが、例えば、下記一般式(3−1)または(3−2)で表される基であることが好ましい。なお、上記一般式(2)中のRが複数の酸解離性基によって置換されている場合、Rは、それぞれ独立に下記一般式(3−1)または(3−2)で表される基とすることができる。 R in the general formula (2) is each independently a hydrogen atom or a monovalent acid dissociable group. However, at least one of R is preferably a monovalent acid dissociable group. Although the structure of the acid dissociable group is not particularly limited, for example, a group represented by the following general formula (3-1) or (3-2) is preferable. In addition, when R in the general formula (2) is substituted with a plurality of acid dissociable groups, each R is independently a group represented by the following general formula (3-1) or (3-2) It can be.
一般式(3−1)において、R1は、ヘテロ原子を含んでも良い置換基で置換された、または非置換の炭素数1〜40の、直鎖状、分岐状または環状構造を有するアルキル基であり、mは0〜3の整数である。また、一般式(3−2)において、R2は、ヘテロ原子を含んでも良い置換基で置換された、または非置換の炭素数1〜40の、直鎖状、分岐状または環状構造を有するアルキル基であり、R3は水素原子または炭素数1〜5のアルキル基である。In General Formula (3-1), R 1 is an alkyl group having a linear, branched, or cyclic structure having 1 to 40 carbon atoms that is substituted or unsubstituted with a substituent that may include a hetero atom. And m is an integer of 0-3. In General Formula (3-2), R 2 has a linear, branched, or cyclic structure having 1 to 40 carbon atoms that is substituted or unsubstituted with a substituent that may include a hetero atom. An alkyl group, and R 3 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
上記一般式(3−1)で表される基としては、例えば、下記一般式(6−1)〜(6−9)で表される基などを挙げることができる。 Examples of the group represented by the general formula (3-1) include groups represented by the following general formulas (6-1) to (6-9).
(上記一般式(6−1)〜(6−9)において、R4は炭素数1〜5のアルキル基であり、mは1〜3の整数である)(In the above general formulas (6-1) to (6-9), R 4 is an alkyl group having 1 to 5 carbon atoms, and m is an integer of 1 to 3)
なお、上記一般式(6−1)〜(6−9)で表される基の中でも、一般式(6−1)、(6−8)または(6−9)で表される基が好ましい。 Of the groups represented by the general formulas (6-1) to (6-9), groups represented by the general formula (6-1), (6-8), or (6-9) are preferable. .
上記一般式(6−1)〜(6−9)中のR4は、低級アルキル基(炭素数1〜5のアルキル基)であり、具体的には、メチル基、エチル基、プロピル基、イソプロピル基、n−ブチル基、イソブチル基、tert−ブチル基、ペンチル基、イソペンチル基、ネオペンチル基などの低級の直鎖状または分岐状のアルキル基を挙げることができる。これらのうち、メチル基またはエチル基が好ましく、メチル基であることが更に好ましい。R 4 in the general formulas (6-1) to (6-9) is a lower alkyl group (an alkyl group having 1 to 5 carbon atoms), specifically, a methyl group, an ethyl group, a propyl group, Examples include lower linear or branched alkyl groups such as isopropyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, isopentyl group, and neopentyl group. Of these, a methyl group or an ethyl group is preferable, and a methyl group is more preferable.
なお、上記一般式(3−1)中のR1は、具体的には、2−メチル−2−アダマンチル基、2−エチル−2−アダマンチル基、1−エチルシクロペンチル基、または1−メチルシクロペンチル基、tert−ブチル基であることが好ましい。In addition, R 1 in the general formula (3-1) is specifically 2-methyl-2-adamantyl group, 2-ethyl-2-adamantyl group, 1-ethylcyclopentyl group, or 1-methylcyclopentyl. And a tert-butyl group.
また、上記一般式(3−1)で表される基としては、具体的には、2−メチル−2−アダマンチルオキシカルボニルメチル基、2−エチル−2−アダマンチルオキシカルボニルメチル基、1−エチルシクロペンチルオキシカルボニルメチル基、1−メチルシクロペンチルオキシカルボニルメチル基、tert−ブトキシカルボニルメチル基、tert−ブトキシカルボニル基であることが好ましい。 Specific examples of the group represented by the general formula (3-1) include 2-methyl-2-adamantyloxycarbonylmethyl group, 2-ethyl-2-adamantyloxycarbonylmethyl group, and 1-ethyl. A cyclopentyloxycarbonylmethyl group, a 1-methylcyclopentyloxycarbonylmethyl group, a tert-butoxycarbonylmethyl group, and a tert-butoxycarbonyl group are preferable.
上記一般式(3−2)で表される基としては、例えば、下記一般式(7−1)〜(7−14)で表される基などを挙げることができる。 Examples of the group represented by the general formula (3-2) include groups represented by the following general formulas (7-1) to (7-14).
上記一般式(7−1)〜(7−14)において、R3およびR5は、水素原子または炭素数1〜5のアルキル基である。炭素数1〜5のアルキル基としては、例えば、メチル基、エチル基、プロピル基、イソプロピル基、n−ブチル基、イソブチル基、tert−ブチル基、ペンチル基、イソペンチル基、ネオペンチル基等の低級の直鎖状または分岐状のアルキル基を挙げることができる。また、上記一般式(7−1)〜(7−10)において、Lは0〜2の整数であり、0または1であることが好ましい。In the above general formulas (7-1) to (7-14), R 3 and R 5 are a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. Examples of the alkyl group having 1 to 5 carbon atoms include lower groups such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, isopentyl, and neopentyl. A linear or branched alkyl group can be mentioned. Moreover, in the said General Formula (7-1)-(7-10), L is an integer of 0-2, and it is preferable that it is 0 or 1.
上記一般式(3−2)で表される基としては、具体的には、2−アダマンチルオキシメチル基、下記一般式(8)下記一般式(9)または下記一般式(10)で表される基が好ましい。 Specifically, the group represented by the general formula (3-2) is represented by a 2-adamantyloxymethyl group, the following general formula (8), the following general formula (9), or the following general formula (10). Are preferred.
[2]感放射線性組成物:
本発明の感放射線性組成物は、上述した(a)化合物と、(b)放射線が照射されることにより酸を発生する感放射線性酸発生剤と、を含有するものである。本発明の感放射線性組成物は、(a)化合物を含有することにより、ベンゼン環骨格を有する化合物を含有することになるためエッチング耐性に優れる。また、本発明の感放射線性組成物は、含有する(a)化合物が、樹脂ではなく低分子の化合物であるため、樹脂に起因する凝集が生じることがなく、ナノエッジラフネスに優れる。更に、本発明の感放射線性組成物は、化学増幅型レジストと同様に酸解離性基を導入しているため、感度に優れる。そして、リソグラフィープロセスにおいて、電子線または極紫外線に有効に感応し、ナノエッジラフネス、エッチング耐性、感度に優れ、微細パターンを高精度に、かつ、安定して形成することができるものである。[2] Radiation sensitive composition:
The radiation-sensitive composition of the present invention contains the above-described compound (a) and (b) a radiation-sensitive acid generator that generates an acid when irradiated with radiation. The radiation-sensitive composition of the present invention is excellent in etching resistance because it contains a compound having a benzene ring skeleton by containing the compound (a). In addition, since the compound (a) contained in the radiation-sensitive composition of the present invention is not a resin but a low-molecular compound, aggregation due to the resin does not occur, and the nano edge roughness is excellent. Furthermore, the radiation-sensitive composition of the present invention is excellent in sensitivity because an acid-dissociable group is introduced in the same manner as a chemically amplified resist. In the lithography process, it effectively responds to an electron beam or extreme ultraviolet rays, is excellent in nano edge roughness, etching resistance, and sensitivity, and can form a fine pattern with high accuracy and stability.
[2−1]感放射線性酸発生剤:
上記(b)感放射線性酸発生剤は、リソグラフィープロセスにおいて、感放射線性組成物に電子線等を照射したときに、感放射線性組成物内で酸を発生する物質であり、この発生した酸の作用によって既に上述した(a)化合物の酸解離性基を解離させることができる。[2-1] Radiation sensitive acid generator:
The (b) radiation-sensitive acid generator is a substance that generates an acid in the radiation-sensitive composition when the radiation-sensitive composition is irradiated with an electron beam or the like in a lithography process. By the action, the acid dissociable group of the compound (a) already described above can be dissociated.
(b)感放射線性酸発生剤としては、酸発生効率、耐熱性などが良好である観点から、例えば、オニウム塩、ジアゾメタン化合物、及びスルホンイミド化合物よりなる群から選択される少なくとも一種であることが好ましい。なお、これらは、単独でまたは複数を組み合わせて使用することができる。 (B) The radiation sensitive acid generator is, for example, at least one selected from the group consisting of onium salts, diazomethane compounds, and sulfonimide compounds from the viewpoint of good acid generation efficiency, heat resistance, and the like. Is preferred. In addition, these can be used individually or in combination of multiple.
オニウム塩としては、例えば、ヨードニウム塩、スルホニウム塩、ホスホニウム塩、ジアゾニウム塩、ピリジニウム塩等を挙げることができる。ここで、オニウム塩の具体例としては、トリフェニルスルホニウムトリフルオロメタンスルホネート、トリフェニルスルホニウムノナフルオロ−n−ブタンスルホネート、トリフェニルスルホニウムベンゼンスルホネート、トリフェニルスルホニウム10−カンファースルホネート、トリフェニルスルホニウムn−オクタンスルホネート、トリフェニルスルホニウム4−トリフルオロメチルベンゼンスルホネート、トリフェニルスルホニウムナフタレンスルホネート、トリフェニルスルホニウムパーフルオロベンゼンスルホネート、トリフェニルスルホニウム1,1,2,2−テトラフルオロ−2−(テトラシクロ[4.4.0.12,5.17,10]ドデカン−8−イル)エタンスルホネート、トリフェニルスルホニウム1,1−ジフルオロ−2−(ビシクロ[2.2.1]ヘプタン−2−イル)エタンスルホネート;Examples of onium salts include iodonium salts, sulfonium salts, phosphonium salts, diazonium salts, pyridinium salts, and the like. Here, specific examples of the onium salt include triphenylsulfonium trifluoromethanesulfonate, triphenylsulfonium nonafluoro-n-butanesulfonate, triphenylsulfoniumbenzenesulfonate, triphenylsulfonium 10-camphorsulfonate, and triphenylsulfonium n-octanesulfonate. , Triphenylsulfonium 4-trifluoromethylbenzenesulfonate, triphenylsulfonium naphthalenesulfonate, triphenylsulfonium perfluorobenzenesulfonate, triphenylsulfonium 1,1,2,2-tetrafluoro-2- (tetracyclo [4.4.0 .1 2,5 .1 7,10] dodecane-8-yl) ethanesulfonate, triphenylsulfonium 1,1-difluoro - - (bicyclo [2.2.1] heptan-2-yl) ethanesulfonate;
(4−t−ブトキシフェニル)ジフェニルスルホニウムトリフルオロメタンスルホネート、(4−t−ブトキシフェニル)ジフェニルスルホニウムノナフルオロ−n−ブタンスルホネート、(4−t−ブトキシフェニル)ジフェニルスルホニウムパーフルオロ−n−オクタンスルホネート、 (4-t-butoxyphenyl) diphenylsulfonium trifluoromethanesulfonate, (4-t-butoxyphenyl) diphenylsulfonium nonafluoro-n-butanesulfonate, (4-t-butoxyphenyl) diphenylsulfonium perfluoro-n-octanesulfonate,
(4−ヒドロキシフェニル)ジフェニルスルホニウムトリフルオロメタンスルホネート、(4−ヒドロキシフェニル)ジフェニルスルホニウムノナフルオロ−n−ブタンスルホネート、(4−ヒドロキシフェニル)ジフェニルスルホニウムパーフルオロ−n−オクタンスルホネート、(4−ヒドロキシフェニル)ジフェニルスルホニウム10−カンファースルホネート、(4−ヒドロキシフェニル)ジフェニルスルホニウムn−オクタンスルホネート、 (4-hydroxyphenyl) diphenylsulfonium trifluoromethanesulfonate, (4-hydroxyphenyl) diphenylsulfonium nonafluoro-n-butanesulfonate, (4-hydroxyphenyl) diphenylsulfonium perfluoro-n-octanesulfonate, (4-hydroxyphenyl) Diphenylsulfonium 10-camphorsulfonate, (4-hydroxyphenyl) diphenylsulfonium n-octanesulfonate,
トリス(4−メトキシフェニル)スルホニウムトリフルオロメタンスルホネート、トリス(4−メトキシフェニル)スルホニウムノナフルオロ−n−ブタンスルホネート、トリス(4−メトキシフェニル)スルホニウムパーフルオロ−n−オクタンスルホネート、トリス(4−メトキシフェニル)スルホニウム10−カンファースルホネート、 Tris (4-methoxyphenyl) sulfonium trifluoromethanesulfonate, tris (4-methoxyphenyl) sulfonium nonafluoro-n-butanesulfonate, tris (4-methoxyphenyl) sulfonium perfluoro-n-octanesulfonate, tris (4-methoxyphenyl) ) Sulfonium 10-camphorsulfonate,
(4−フルオロフェニル)ジフェニルスルホニウムトリフルオロメタンスルホネート、(4−フルオロフェニル)ジフェニルスルホニウムノナフルオロ−n−ブタンスルホネート、(4−フルオロフェニル)ジフェニルスルホニウム10−カンファースルホネート; (4-fluorophenyl) diphenylsulfonium trifluoromethanesulfonate, (4-fluorophenyl) diphenylsulfonium nonafluoro-n-butanesulfonate, (4-fluorophenyl) diphenylsulfonium 10-camphorsulfonate;
トリス(4−フルオロフェニル)スルホニウムトリフルオロメタンスルホネート、トリス(4−フルオロフェニル)スルホニウムノナフルオロ−n−ブタンスルホネート、トリス(4−フルオロフェニル)スルホニウム10−カンファースルホネート、トリス(4−フルオロフェニル)スルホニウムp−トルエンスルホネート、トリス(4−トリフルオロメチルフェニル)スルホニウムトリフルオロメタンスルホネート; Tris (4-fluorophenyl) sulfonium trifluoromethanesulfonate, tris (4-fluorophenyl) sulfonium nonafluoro-n-butanesulfonate, tris (4-fluorophenyl) sulfonium 10-camphorsulfonate, tris (4-fluorophenyl) sulfonium p -Toluenesulfonate, tris (4-trifluoromethylphenyl) sulfonium trifluoromethanesulfonate;
2,4,6−トリメチルフェニルジフェニルスルホニウムトリフルオロメタンスルホネート、2,4,6−トリメチルフェニルジフェニルスルホニウム2,4−ジフルオロベンゼンスルホネート、2,4,6−トリメチルフェニルジフェニルスルホニウム4−トリフルオロメチルベンゼンスルホネート; 2,4,6-trimethylphenyldiphenylsulfonium trifluoromethanesulfonate, 2,4,6-trimethylphenyldiphenylsulfonium 2,4-difluorobenzenesulfonate, 2,4,6-trimethylphenyldiphenylsulfonium 4-trifluoromethylbenzenesulfonate;
ジフェニルヨードニウムトリフルオロメタンスルホネート、ジフェニルヨードニウムノナフルオロ−n−ブタンスルホネート、ジフェニルヨードニウムパーフルオロ−n−オクタンスルホネート、ジフェニルヨードニウム10−カンファースルホネート、ジフェニルヨードニウムn−オクタンスルホネート、 Diphenyliodonium trifluoromethanesulfonate, diphenyliodonium nonafluoro-n-butanesulfonate, diphenyliodonium perfluoro-n-octanesulfonate, diphenyliodonium 10-camphorsulfonate, diphenyliodonium n-octanesulfonate,
ビス(4−t−ブチルフェニル)ヨードニウムトリフルオロメタンスルホネート、ビス(4−t−ブチルフェニル)ヨードニウムノナフルオロ−n−ブタンスルホネート、ビス(4−t−ブチルフェニル)ヨードニウムパーフルオロ−n−オクタンスルホネート、ビス(4−t−ブチルフェニル)ヨードニウム10−カンファースルホネート、ビス(4−t−ブチルフェニル)ヨードニウムn−オクタンスルホネート、 Bis (4-t-butylphenyl) iodonium trifluoromethanesulfonate, bis (4-t-butylphenyl) iodonium nonafluoro-n-butanesulfonate, bis (4-t-butylphenyl) iodonium perfluoro-n-octanesulfonate, Bis (4-t-butylphenyl) iodonium 10-camphorsulfonate, bis (4-t-butylphenyl) iodonium n-octanesulfonate,
(4−メトキシフェニル)フェニルヨードニウムトリフルオロメタンスルホネート、(4−メトキシフェニル)フェニルヨードニウムノナフルオロ−n−ブタンスルホネート、(4−メトキシフェニル)フェニルヨードニウムパーフルオロ−n−オクタンスルホネート、 (4-methoxyphenyl) phenyliodonium trifluoromethanesulfonate, (4-methoxyphenyl) phenyliodonium nonafluoro-n-butanesulfonate, (4-methoxyphenyl) phenyliodonium perfluoro-n-octanesulfonate,
(4−フルオロフェニル)フェニルヨードニウムトリフルオロメタンスルホネート、(4−フルオロフェニル)フェニルヨードニウムノナフルオロ−n−ブタンスルホネート、(4−フルオロフェニル)フェニルヨードニウム10−カンファースルホネート; (4-fluorophenyl) phenyliodonium trifluoromethanesulfonate, (4-fluorophenyl) phenyliodonium nonafluoro-n-butanesulfonate, (4-fluorophenyl) phenyliodonium 10-camphorsulfonate;
ビス(4−フルオロフェニル)ヨードニウムトリフルオロメタンスルホネート、ビス(4−フルオロフェニル)ヨードニウムノナフルオロ−n−ブタンスルホネート、ビス(4−フルオロフェニル)ヨードニウム10−カンファースルホネート; Bis (4-fluorophenyl) iodonium trifluoromethanesulfonate, bis (4-fluorophenyl) iodonium nonafluoro-n-butanesulfonate, bis (4-fluorophenyl) iodonium 10-camphorsulfonate;
ビス(4−クロロフェニル)ヨードニウムトリフルオロメタンスルホネート、ビス(4−クロロフェニル)ヨードニウムノナフルオロ−n−ブタンスルホネート、ビス(4−クロロフェニル)ヨードニウムパーフルオロ−n−オクタンスルホネート、ビス(4−クロロフェニル)ヨードニウム10−カンファースルホネート、ビス(4−クロロフェニル)ヨードニウムn−オクタンスルホネート、ビス(4−クロロフェニル)ヨードニウム4−トリフルオロメチルベンゼンスルホネート、ビス(4−クロロフェニル)ヨードニウムパーフルオロベンゼンスルホネート; Bis (4-chlorophenyl) iodonium trifluoromethanesulfonate, bis (4-chlorophenyl) iodonium nonafluoro-n-butanesulfonate, bis (4-chlorophenyl) iodonium perfluoro-n-octanesulfonate, bis (4-chlorophenyl) iodonium 10- Camphorsulfonate, bis (4-chlorophenyl) iodonium n-octanesulfonate, bis (4-chlorophenyl) iodonium 4-trifluoromethylbenzenesulfonate, bis (4-chlorophenyl) iodonium perfluorobenzenesulfonate;
ビス(4−トリフルオロメチルフェニル)ヨードニウムトリフルオロメタンスルホネート、ビス(4−トリフルオロメチルフェニル)ヨードニウムノナフルオロ−n−ブタンスルホネート、ビス(4−トリフルオロメチルフェニル)ヨードニウムパーフルオロ−n−オクタンスルホネート、ビス(4−トリフルオロメチルフェニル)ヨードニウムn−ドデシルベンゼンスルホネート、ビス(4−トリフルオロメチルフェニル)ヨードニウムp−トルエンスルホネート、ビス(4−トリフルオロメチルフェニル)ヨードニウムベンゼンスルホネート、ビス(4−トリフルオロメチルフェニル)ヨードニウム10−カンファースルホネート、ビス(4−トリフルオロメチルフェニル)ヨードニウムn−オクタンスルホネート、ビス(4−トリフルオロメチルフェニル)ヨードニウム4−トリフルオロメチルベンゼンスルホネート、ビス(4−トリフルオロメチルフェニル)ヨードニウムパーフルオロベンゼンスルホネート; Bis (4-trifluoromethylphenyl) iodonium trifluoromethanesulfonate, bis (4-trifluoromethylphenyl) iodonium nonafluoro-n-butanesulfonate, bis (4-trifluoromethylphenyl) iodonium perfluoro-n-octanesulfonate, Bis (4-trifluoromethylphenyl) iodonium n-dodecylbenzenesulfonate, bis (4-trifluoromethylphenyl) iodonium p-toluenesulfonate, bis (4-trifluoromethylphenyl) iodoniumbenzenesulfonate, bis (4-trifluoro Methylphenyl) iodonium 10-camphorsulfonate, bis (4-trifluoromethylphenyl) iodonium n-octanesulfonate, bis (4-trifluoro) B methylphenyl) iodonium 4-trifluoromethyl benzenesulfonate, bis (4-trifluoromethylphenyl) iodonium perfluoro sulfonate;
これらの中では、トリフェニルスルホニウムトリフルオロメタンスルホネート、トリフェニルスルホニウムノナフルオロ−n−ブタンスルホネート、トリフェニルスルホニウム10−カンファースルホネート、(4−ヒドロキシフェニル)ジフェニルスルホニウムトリフルオロメタンスルホネート、(4−ヒドロキシフェニル)ジフェニルスルホニウムノナフルオロ−n−ブタンスルホネート、トリス(4−メトキシフェニル)スルホニウムトリフルオロメタンスルホネート、トリス(4−メトキシフェニル)スルホニウムノナフルオロ−n−ブタンスルホネート、(4−フルオロフェニル)ジフェニルスルホニウムトリフルオロメタンスルホネート、(4−フルオロフェニル)ジフェニルスルホニウムノナフルオロ−n−ブタンスルホネート、2,4,6−トリメチルフェニルジフェニルスルホニウムトリフルオロメタンスルホネート、2,4,6−トリメチルフェニルジフェニルスルホニウム2,4−ジフルオロベンゼンスルホネート、2,4,6−トリメチルフェニルジフェニルスルホニウム4−トリフルオロメチルベンゼンスルホネート、ジフェニルヨードニウムトリフルオロメタンスルホネート、ジフェニルヨードニウムノナフルオロ−n−ブタンスルホネート、ジフェニルヨードニウム10−カンファースルホネート、ビス(4−t−ブチルフェニル)ヨードニウムトリフルオロメタンスルホネート、ビス(4−t−ブチルフェニル)ヨードニウムノナフルオロ−n−ブタンスルホネート、ビス(4−t−ブチルフェニル)ヨードニウム10−カンファースルホネート、(4−フルオロフェニル)フェニルヨードニウムトリフルオロメタンスルホネート、(4−フルオロフェニル)フェニルヨードニウムノナフルオロ−n−ブタンスルホネート、(4−フルオロフェニル)フェニルヨードニウム10−カンファースルホネート、ビス(4−フルオロフェニル)ヨードニウムトリフルオロメタンスルホネート、ビス(4−フルオロフェニル)ヨードニウムノナフルオロ−n−ブタンスルホネート、ビス(4−フルオロフェニル)ヨードニウム10−カンファースルホネート、トリス(4−トリフルオロメチルフェニル)スルホニウムトリフルオロメタンスルホネートが好ましい。これらは、単独で、または複数を組み合わせて使用することができる。 Among these, triphenylsulfonium trifluoromethanesulfonate, triphenylsulfonium nonafluoro-n-butanesulfonate, triphenylsulfonium 10-camphorsulfonate, (4-hydroxyphenyl) diphenylsulfonium trifluoromethanesulfonate, (4-hydroxyphenyl) diphenyl Sulfonium nonafluoro-n-butanesulfonate, tris (4-methoxyphenyl) sulfonium trifluoromethanesulfonate, tris (4-methoxyphenyl) sulfonium nonafluoro-n-butanesulfonate, (4-fluorophenyl) diphenylsulfonium trifluoromethanesulfonate, 4-Fluorophenyl) diphenylsulfonium nonafluoro-n-butanesulfonate 2,4,6-trimethylphenyldiphenylsulfonium trifluoromethanesulfonate, 2,4,6-trimethylphenyldiphenylsulfonium 2,4-difluorobenzenesulfonate, 2,4,6-trimethylphenyldiphenylsulfonium 4-trifluoromethylbenzenesulfonate Diphenyliodonium trifluoromethanesulfonate, diphenyliodonium nonafluoro-n-butanesulfonate, diphenyliodonium 10-camphorsulfonate, bis (4-t-butylphenyl) iodonium trifluoromethanesulfonate, bis (4-t-butylphenyl) iodonium nonafluoro -N-butanesulfonate, bis (4-t-butylphenyl) iodonium 10-camphorsulfonate (4-fluorophenyl) phenyliodonium trifluoromethanesulfonate, (4-fluorophenyl) phenyliodonium nonafluoro-n-butanesulfonate, (4-fluorophenyl) phenyliodonium 10-camphorsulfonate, bis (4-fluorophenyl) iodonium trifluoro Lomethanesulfonate, bis (4-fluorophenyl) iodonium nonafluoro-n-butanesulfonate, bis (4-fluorophenyl) iodonium 10-camphorsulfonate, and tris (4-trifluoromethylphenyl) sulfonium trifluoromethanesulfonate are preferred. These can be used alone or in combination.
ジアゾメタン化合物としては、例えば、ビス(トリフルオロメタンスルホニル)ジアゾメタン、ビス(シクロヘキシルスルホニル)ジアゾメタン、ビス(3,3−ジメチル−1,5−ジオキサスピロ[5.5]ドデカン−8−スルホニル)ジアゾメタン、ビス(1,4−ジオキサスピロ[4.5]デカン−7−スルホニル)ジアゾメタン、ビス(t−ブチルスルホニル)ジアゾメタン等を挙げることができる。 Examples of the diazomethane compound include bis (trifluoromethanesulfonyl) diazomethane, bis (cyclohexylsulfonyl) diazomethane, bis (3,3-dimethyl-1,5-dioxaspiro [5.5] dodecane-8-sulfonyl) diazomethane, bis ( 1,4-dioxaspiro [4.5] decane-7-sulfonyl) diazomethane, bis (t-butylsulfonyl) diazomethane, and the like can be given.
これらの中では、ビス(シクロヘキシルスルホニル)ジアゾメタン、ビス(3,3−ジメチル−1,5−ジオキサスピロ[5.5]ドデカン−8−スルホニル)ジアゾメタン、ビス(1,4−ジオキサスピロ[4.5]デカン−7−スルホニル)ジアゾメタンが好ましい。これらは、単独で、または複数を組み合わせて使用することができる。 Among these, bis (cyclohexylsulfonyl) diazomethane, bis (3,3-dimethyl-1,5-dioxaspiro [5.5] dodecane-8-sulfonyl) diazomethane, bis (1,4-dioxaspiro [4.5] Decane-7-sulfonyl) diazomethane is preferred. These can be used alone or in combination.
スルホンイミド化合物としては、例えば、N−(トリフルオロメチルスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(トリフルオロメチルスルホニルオキシ)−7−オキサビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(トリフルオロメチルスルホニルオキシ)ビシクロ[2.2.1]ヘプタン−5,6−オキシ−2,3−ジカルボキシイミド、 Examples of the sulfonimide compound include N- (trifluoromethylsulfonyloxy) bicyclo [2.2.1] hept-5-ene-2,3-dicarboximide, N- (trifluoromethylsulfonyloxy) -7. -Oxabicyclo [2.2.1] hept-5-ene-2,3-dicarboximide, N- (trifluoromethylsulfonyloxy) bicyclo [2.2.1] heptane-5,6-oxy-2 , 3-dicarboximide,
N−(10−カンファースルホニルオキシ)スクシンイミド、N−(10−カンファースルホニルオキシ)フタルイミド、N−(10−カンファースルホニルオキシ)−7−オキサビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(10−カンファースルホニルオキシ)ビシクロ[2.2.1]ヘプタン−5,6−オキシ−2,3−ジカルボキシイミド、N−(10−カンファースルホニルオキシ)ナフチルイミド、N−〔(5−メチル−5−カルボキシメチルビシクロ[2.2.1]ヘプタン−2−イル)スルホニルオキシ〕スクシンイミド; N- (10-camphorsulfonyloxy) succinimide, N- (10-camphorsulfonyloxy) phthalimide, N- (10-camphorsulfonyloxy) -7-oxabicyclo [2.2.1] hept-5-ene-2 , 3-dicarboximide, N- (10-camphorsulfonyloxy) bicyclo [2.2.1] heptane-5,6-oxy-2,3-dicarboximide, N- (10-camphorsulfonyloxy) naphthyl Imido, N-[(5-methyl-5-carboxymethylbicyclo [2.2.1] heptan-2-yl) sulfonyloxy] succinimide;
N−(n−オクチルスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(n−オクチルスルホニルオキシ)ビシクロ[2.2.1]ヘプタン−5,6−オキシ−2,3−ジカルボキシイミド、 N- (n-octylsulfonyloxy) bicyclo [2.2.1] hept-5-ene-2,3-dicarboximide, N- (n-octylsulfonyloxy) bicyclo [2.2.1] heptane- 5,6-oxy-2,3-dicarboximide,
N−(パーフルオロフェニルスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(パーフルオロフェニルスルホニルオキシ)−7−オキサビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(パーフルオロフェニルスルホニルオキシ)ビシクロ[2.2.1]ヘプタン−5,6−オキシ−2,3−ジカルボキシイミド、 N- (perfluorophenylsulfonyloxy) bicyclo [2.2.1] hept-5-ene-2,3-dicarboximide, N- (perfluorophenylsulfonyloxy) -7-oxabicyclo [2.2. 1] hept-5-ene-2,3-dicarboximide, N- (perfluorophenylsulfonyloxy) bicyclo [2.2.1] heptane-5,6-oxy-2,3-dicarboximide,
N−(ノナフルオロ−n−ブチルスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(ノナフルオロ−n−ブチルスルホニルオキシ)−7−オキサビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(ノナフルオロ−n−ブチルスルホニルオキシ)ビシクロ[2.2.1]ヘプタン−5,6−オキシ−2,3−ジカルボキシイミド、 N- (nonafluoro-n-butylsulfonyloxy) bicyclo [2.2.1] hept-5-ene-2,3-dicarboximide, N- (nonafluoro-n-butylsulfonyloxy) -7-oxabicyclo [ 2.2.1] Hept-5-ene-2,3-dicarboximide, N- (nonafluoro-n-butylsulfonyloxy) bicyclo [2.2.1] heptane-5,6-oxy-2,3 -Dicarboximide,
N−(パーフルオロ−n−オクチルスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(パーフルオロ−n−オクチルスルホニルオキシ)−7−オキサビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(パーフルオロ−n−オクチルスルホニルオキシ)ビシクロ[2.2.1]ヘプタン−5,6−オキシ−2,3−ジカルボキシイミド、 N- (perfluoro-n-octylsulfonyloxy) bicyclo [2.2.1] hept-5-ene-2,3-dicarboximide, N- (perfluoro-n-octylsulfonyloxy) -7-oxa Bicyclo [2.2.1] hept-5-ene-2,3-dicarboximide, N- (perfluoro-n-octylsulfonyloxy) bicyclo [2.2.1] heptane-5,6-oxy- 2,3-dicarboximide,
これらの中では、N−(トリフルオロメチルスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(10−カンファースルホニルオキシ)スクシンイミド、N−〔(5−メチル−5−カルボキシメチルビシクロ[2.2.1]ヘプタン−2−イル)スルホニルオキシ〕スクシンイミドが好ましい。これらは、単独で、または複数を組み合わせて使用することができる。 Among these, N- (trifluoromethylsulfonyloxy) bicyclo [2.2.1] hept-5-ene-2,3-dicarboximide, N- (10-camphorsulfonyloxy) succinimide, N- [ (5-Methyl-5-carboxymethylbicyclo [2.2.1] heptan-2-yl) sulfonyloxy] succinimide is preferred. These can be used alone or in combination.
(b)感放射線性酸発生剤の使用量は、(a)化合物100質量部に対して、0.1〜30質量部であることが好ましく、0.5〜25質量部であることが更に好ましい。(b)感放射線性酸発生剤の使用量が0.1質量部未満であると、感度及び現像性が低下するおそれがある。一方、30質量部超であると、放射線に対する透明性、パターン形状、耐熱性等が低下するおそれがある。 The amount of the (b) radiation sensitive acid generator used is preferably 0.1 to 30 parts by mass, and more preferably 0.5 to 25 parts by mass with respect to 100 parts by mass of the compound (a). preferable. (B) There exists a possibility that a sensitivity and developability may fall that the usage-amount of a radiation sensitive acid generator is less than 0.1 mass part. On the other hand, if it exceeds 30 parts by mass, transparency to radiation, pattern shape, heat resistance and the like may be reduced.
[2−2](c)酸拡散制御剤:
本発明の感放射線性組成物は、(c)酸拡散制御剤を更に含有することが好ましい。(c)酸拡散制御剤は、露光により(b)感放射線性酸発生剤から生じる酸のレジスト被膜中における拡散現象を制御し、非露光領域における好ましくない化学反応を抑制する作用を有する成分である。このような(c)酸拡散制御剤を配合することにより、得られる感放射線性組成物の貯蔵安定性が向上し、また、レジストとしての解像度が更に向上するとともに、露光から露光後の加熱処理までの引き置き時間(PED)の変動によるレジストパターンの線幅変化を抑えることができ、プロセス安定性に極めて優れた感放射線性組成物が得られる。[2-2] (c) Acid diffusion controller:
The radiation-sensitive composition of the present invention preferably further contains (c) an acid diffusion controller. (C) The acid diffusion control agent is a component having an action of controlling the diffusion phenomenon in the resist film of the acid generated from the (b) radiation sensitive acid generator by exposure and suppressing undesirable chemical reaction in the non-exposed region. is there. By blending such an acid diffusion control agent (c), the storage stability of the resulting radiation-sensitive composition is improved, the resolution as a resist is further improved, and the heat treatment from exposure to exposure is performed. The change of the line width of the resist pattern due to the fluctuation of the holding time (PED) until the time can be suppressed, and a radiation-sensitive composition having extremely excellent process stability can be obtained.
(c)酸拡散制御剤としては、例えば、含窒素有機化合物または感光性塩基性化合物が好ましい。上記含窒素有機化合物としては、例えば、下記一般式(11)で表される化合物(以下、「含窒素化合物(i)」という)、同一分子内に窒素原子を2個有する化合物(以下、「含窒素化合物(ii)」という)、窒素原子を3個以上有するポリアミノ化合物や重合体(以下、これらをまとめて「含窒素化合物(iii)」という)、アミド基含有化合物、ウレア化合物、含窒素複素環化合物等を挙げることができる。 (C) As an acid diffusion controlling agent, for example, a nitrogen-containing organic compound or a photosensitive basic compound is preferable. Examples of the nitrogen-containing organic compound include a compound represented by the following general formula (11) (hereinafter referred to as “nitrogen-containing compound (i)”), a compound having two nitrogen atoms in the same molecule (hereinafter referred to as “ Nitrogen-containing compound (ii) ”), polyamino compounds and polymers having three or more nitrogen atoms (hereinafter collectively referred to as“ nitrogen-containing compound (iii) ”), amide group-containing compounds, urea compounds, nitrogen-containing compounds Examples include heterocyclic compounds.
(前記一般式(11)において、各R6は相互に独立に水素原子、置換されていてもよい、直鎖状、分岐状若しくは環状アルキル基、置換されていてもよいアリール基、または置換されていてもよいアラルキル基である)(In the general formula (11), each R 6 is independently a hydrogen atom, an optionally substituted linear, branched or cyclic alkyl group, an optionally substituted aryl group, or a substituted group. It is an aralkyl group that may be
含窒素化合物(i)としては、例えば、n−ヘキシルアミン、n−ヘプチルアミン、n−オクチルアミン、n−ノニルアミン、n−デシルアミン、シクロヘキシルアミン等のモノ(シクロ)アルキルアミン類;ジ−n−ブチルアミン、ジ−n−ペンチルアミン、ジ−n−ヘキシルアミン、ジ−n−ヘプチルアミン、ジ−n−オクチルアミン、ジ−n−ノニルアミン、ジ−n−デシルアミン、シクロヘキシルメチルアミン、ジシクロヘキシルアミン等のジ(シクロ)アルキルアミン類;トリエチルアミン、トリ−n−プロピルアミン、トリ−n−ブチルアミン、トリ−n−ペンチルアミン、トリ−n−ヘキシルアミン、トリ−n−ヘプチルアミン、トリ−n−オクチルアミン、トリ−n−ノニルアミン、トリ−n−デシルアミン、シクロヘキシルジメチルアミン、メチルジシクロヘキシルアミン、トリシクロヘキシルアミン等のトリ(シクロ)アルキルアミン類;トリエタノールアミン等の置換アルキルアミン;アニリン、N−メチルアニリン、N,N−ジメチルアニリン、2−メチルアニリン、3−メチルアニリン、4−メチルアニリン、4−ニトロアニリン、ジフェニルアミン、トリフェニルアミン、ナフチルアミン、2,4,6−トリ−tert−ブチル−N−メチルアニリン、N−フェニルジエタノールアミン、2,6−ジイソプロピルアニリン等の芳香族アミン類が好ましい。 Examples of the nitrogen-containing compound (i) include mono (cyclo) alkylamines such as n-hexylamine, n-heptylamine, n-octylamine, n-nonylamine, n-decylamine, cyclohexylamine; di-n- Butylamine, di-n-pentylamine, di-n-hexylamine, di-n-heptylamine, di-n-octylamine, di-n-nonylamine, di-n-decylamine, cyclohexylmethylamine, dicyclohexylamine, etc. Di (cyclo) alkylamines; triethylamine, tri-n-propylamine, tri-n-butylamine, tri-n-pentylamine, tri-n-hexylamine, tri-n-heptylamine, tri-n-octylamine , Tri-n-nonylamine, tri-n-decylamine, cyclohexyl Tri (cyclo) alkylamines such as dimethylamine, methyldicyclohexylamine, tricyclohexylamine; substituted alkylamines such as triethanolamine; aniline, N-methylaniline, N, N-dimethylaniline, 2-methylaniline, 3- Methylaniline, 4-methylaniline, 4-nitroaniline, diphenylamine, triphenylamine, naphthylamine, 2,4,6-tri-tert-butyl-N-methylaniline, N-phenyldiethanolamine, 2,6-diisopropylaniline, etc. Aromatic amines are preferred.
含窒素化合物(ii)としては、例えば、エチレンジアミン、N,N,N’,N’−テトラメチルエチレンジアミン、テトラメチレンジアミン、ヘキサメチレンジアミン、4,4’−ジアミノジフェニルメタン、4,4’−ジアミノジフェニルエーテル、4,4’−ジアミノベンゾフェノン、4,4’−ジアミノジフェニルアミン、2,2−ビス(4−アミノフェニル)プロパン、2−(3−アミノフェニル)−2−(4−アミノフェニル)プロパン、2−(4−アミノフェニル)−2−(3−ヒドロキシフェニル)プロパン、2−(4−アミノフェニル)−2−(4−ヒドロキシフェニル)プロパン、1,4−ビス〔1−(4−アミノフェニル)−1−メチルエチル〕ベンゼン、1,3−ビス〔1−(4−アミノフェニル)−1−メチルエチル〕ベンゼン、ビス(2−ジメチルアミノエチル)エーテル、ビス(2−ジエチルアミノエチル)エーテル、1−(2−ヒドロキシエチル)−2−イミダゾリジノン、2−キノキサリノール、N,N,N’,N’−テトラキス(2−ヒドロキシプロピル)エチレンジアミン、N,N,N’,N”,N”−ペンタメチルジエチレントリアミン等が好ましい。 Examples of the nitrogen-containing compound (ii) include ethylenediamine, N, N, N ′, N′-tetramethylethylenediamine, tetramethylenediamine, hexamethylenediamine, 4,4′-diaminodiphenylmethane, and 4,4′-diaminodiphenylether. 4,4′-diaminobenzophenone, 4,4′-diaminodiphenylamine, 2,2-bis (4-aminophenyl) propane, 2- (3-aminophenyl) -2- (4-aminophenyl) propane, 2, -(4-aminophenyl) -2- (3-hydroxyphenyl) propane, 2- (4-aminophenyl) -2- (4-hydroxyphenyl) propane, 1,4-bis [1- (4-aminophenyl) ) -1-methylethyl] benzene, 1,3-bis [1- (4-aminophenyl) -1-methyl ester Benzene], bis (2-dimethylaminoethyl) ether, bis (2-diethylaminoethyl) ether, 1- (2-hydroxyethyl) -2-imidazolidinone, 2-quinoxalinol, N, N, N ′ , N′-tetrakis (2-hydroxypropyl) ethylenediamine, N, N, N ′, N ″, N ″ -pentamethyldiethylenetriamine and the like are preferable.
含窒素化合物(iii)としては、例えば、ポリエチレンイミン、ポリアリルアミン、2−ジメチルアミノエチルアクリルアミドの重合体等が好ましい。 As the nitrogen-containing compound (iii), for example, polyethyleneimine, polyallylamine, 2-dimethylaminoethylacrylamide polymer and the like are preferable.
上記アミド基含有化合物としては、例えば、N−t−ブトキシカルボニルジ−n−オクチルアミン、N−t−ブトキシカルボニルジ−n−ノニルアミン、N−t−ブトキシカルボニルジ−n−デシルアミン、N−t−ブトキシカルボニルジシクロヘキシルアミン、N−t−ブトキシカルボニル−1−アダマンチルアミン、N−t−ブトキシカルボニル−2−アダマンチルアミン、N−t−ブトキシカルボニル−N−メチル−1−アダマンチルアミン、(S)−(−)−1−(t−ブトキシカルボニル)−2−ピロリジンメタノール、(R)−(+)−1−(t−ブトキシカルボニル)−2−ピロリジンメタノール、N−t−ブトキシカルボニル−4−ヒドロキシピペリジン、N−t−ブトキシカルボニルピロリジン、N−t−ブトキシカルボニルピペラジン、N,N−ジ−t−ブトキシカルボニル−1−アダマンチルアミン、N,N−ジ−t−ブトキシカルボニル−N−メチル−1−アダマンチルアミン、N−t−ブトキシカルボニル−4,4’−ジアミノジフェニルメタン、N,N’−ジ−t−ブトキシカルボニルヘキサメチレンジアミン、N,N,N’N’−テトラ−t−ブトキシカルボニルヘキサメチレンジアミン、N,N’−ジ−t−ブトキシカルボニル−1,7−ジアミノヘプタン、N,N’−ジ−t−ブトキシカルボニル−1,8−ジアミノオクタン、N,N’−ジ−t−ブトキシカルボニル−1,9−ジアミノノナン、N,N’−ジ−t−ブトキシカルボニル−1,10−ジアミノデカン、N,N’−ジ−t−ブトキシカルボニル−1,12−ジアミノドデカン、N,N’−ジ−t−ブトキシカルボニル−4,4’−ジアミノジフェニルメタン、N−t−ブトキシカルボニルベンズイミダゾール、N−t−ブトキシカルボニル−2−メチルベンズイミダゾール、N−t−ブトキシカルボニル−2−フェニルベンズイミダゾール等のN−t−ブトキシカルボニル基含有アミノ化合物のほか、ホルムアミド、N−メチルホルムアミド、N,N−ジメチルホルムアミド、アセトアミド、N−メチルアセトアミド、N,N−ジメチルアセトアミド、プロピオンアミド、ベンズアミド、ピロリドン、N−メチルピロリドン、N−アセチル−1−アダマンチルアミン、イソシアヌル酸トリス(2−ヒドロキシエチル)等が好ましい。 Examples of the amide group-containing compound include Nt-butoxycarbonyldi-n-octylamine, Nt-butoxycarbonyldi-n-nonylamine, Nt-butoxycarbonyldi-n-decylamine, and Nt. -Butoxycarbonyldicyclohexylamine, Nt-butoxycarbonyl-1-adamantylamine, Nt-butoxycarbonyl-2-adamantylamine, Nt-butoxycarbonyl-N-methyl-1-adamantylamine, (S)- (-)-1- (t-butoxycarbonyl) -2-pyrrolidinemethanol, (R)-(+)-1- (t-butoxycarbonyl) -2-pyrrolidinemethanol, Nt-butoxycarbonyl-4-hydroxy Piperidine, Nt-butoxycarbonylpyrrolidine, Nt-butoxycarbo Rupiperazine, N, N-di-t-butoxycarbonyl-1-adamantylamine, N, N-di-t-butoxycarbonyl-N-methyl-1-adamantylamine, Nt-butoxycarbonyl-4,4′- Diaminodiphenylmethane, N, N′-di-t-butoxycarbonylhexamethylenediamine, N, N, N′N′-tetra-t-butoxycarbonylhexamethylenediamine, N, N′-di-t-butoxycarbonyl-1 , 7-diaminoheptane, N, N′-di-t-butoxycarbonyl-1,8-diaminooctane, N, N′-di-t-butoxycarbonyl-1,9-diaminononane, N, N′-di- t-butoxycarbonyl-1,10-diaminodecane, N, N′-di-t-butoxycarbonyl-1,12-diaminododecane, N N'-di-t-butoxycarbonyl-4,4'-diaminodiphenylmethane, Nt-butoxycarbonylbenzimidazole, Nt-butoxycarbonyl-2-methylbenzimidazole, Nt-butoxycarbonyl-2-phenyl In addition to Nt-butoxycarbonyl group-containing amino compounds such as benzimidazole, formamide, N-methylformamide, N, N-dimethylformamide, acetamide, N-methylacetamide, N, N-dimethylacetamide, propionamide, benzamide, Pyrrolidone, N-methylpyrrolidone, N-acetyl-1-adamantylamine, isocyanuric acid tris (2-hydroxyethyl) and the like are preferable.
上記ウレア化合物としては、例えば、尿素、メチルウレア、1,1−ジメチルウレア、1,3−ジメチルウレア、1,1,3,3−テトラメチルウレア、1,3−ジフェニルウレア、トリ−n−ブチルチオウレア等が好ましい。 Examples of the urea compound include urea, methylurea, 1,1-dimethylurea, 1,3-dimethylurea, 1,1,3,3-tetramethylurea, 1,3-diphenylurea, and tri-n-butyl. Thiourea and the like are preferable.
上記含窒素複素環化合物としては、例えば、イミダゾール、4−メチルイミダゾール、4−メチル−2−フェニルイミダゾール、ベンズイミダゾール、2−フェニルベンズイミダゾール、1−ベンジル−2−メチルイミダゾール、1−ベンジル−2−メチル−1H−イミダゾール等のイミダゾール類;ピリジン、2−メチルピリジン、4−メチルピリジン、2−エチルピリジン、4−エチルピリジン、2−フェニルピリジン、4−フェニルピリジン、2−メチル−4−フェニルピリジン、ニコチン、ニコチン酸、ニコチン酸アミド、キノリン、4−ヒドロキシキノリン、8−オキシキノリン、アクリジン、2,2’:6’,2”−ターピリジン等のピリジン類;ピペラジン、1−(2−ヒドロキシエチル)ピペラジン等のピペラジン類のほか、ピラジン、ピラゾール、ピリダジン、キノザリン、プリン、ピロリジン、ピペリジン、ピペリジンエタノール、3−ピペリジノ−1,2−プロパンジオール、モルホリン、4−メチルモルホリン、1−(4−モルホリニル)エタノール、4−アセチルモルホリン、3−(N−モルホリノ)−1,2−プロパンジオール、1,4−ジメチルピペラジン、1,4−ジアザビシクロ[2.2.2]オクタン等が好ましい。 Examples of the nitrogen-containing heterocyclic compound include imidazole, 4-methylimidazole, 4-methyl-2-phenylimidazole, benzimidazole, 2-phenylbenzimidazole, 1-benzyl-2-methylimidazole, 1-benzyl-2. -Imidazoles such as methyl-1H-imidazole; pyridine, 2-methylpyridine, 4-methylpyridine, 2-ethylpyridine, 4-ethylpyridine, 2-phenylpyridine, 4-phenylpyridine, 2-methyl-4-phenyl Pyridines such as pyridine, nicotine, nicotinic acid, nicotinamide, quinoline, 4-hydroxyquinoline, 8-oxyquinoline, acridine, 2,2 ′: 6 ′, 2 ″ -terpyridine; piperazine, 1- (2-hydroxy In addition to piperazines such as ethyl) piperazine Pyrazine, pyrazole, pyridazine, quinosaline, purine, pyrrolidine, piperidine, piperidine ethanol, 3-piperidino-1,2-propanediol, morpholine, 4-methylmorpholine, 1- (4-morpholinyl) ethanol, 4-acetylmorpholine, 3 -(N-morpholino) -1,2-propanediol, 1,4-dimethylpiperazine, 1,4-diazabicyclo [2.2.2] octane and the like are preferable.
また、上記感光性塩基性化合物は、露光領域では対応する中性の断片に効率よく分解し、未露光部では分解せずにそのまま残る成分である。このような感光性塩基性化合物は、非感光性の塩基性化合物に比べて、露光部(露光領域)に発生する酸を有効活用することができるため、感度を向上させることができる。 The photosensitive basic compound is a component that efficiently decomposes into the corresponding neutral fragment in the exposed region and remains as it is without being decomposed in the unexposed portion. Such a photosensitive basic compound can improve the sensitivity because it can effectively use the acid generated in the exposed portion (exposed region) as compared with the non-photosensitive basic compound.
上記感光性塩基性化合物の種類は、上記性質を有する限り、特に制限されるものではないが、例えば、下記一般式(12−1)、一般式(12−2)で表される化合物を好適に用いることができる。 The kind of the photosensitive basic compound is not particularly limited as long as it has the above-mentioned properties. For example, compounds represented by the following general formula (12-1) and general formula (12-2) are preferable. Can be used.
(前記一般式(12−1)及び一般式(12−2)において、R7〜R11はそれぞれ水素原子、ハロゲン原子、置換基を有してもよい炭素数1〜10のアルキル基、または置換基を有してもよい脂環式炭化水素基を表し、X−はOH−、R12OH−、R12COO−を表し、このX−のR12は1価の有機基を表す)(In General Formula (12-1) and General Formula (12-2), R 7 to R 11 are each a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms that may have a substituent, or substituted represents also good alicyclic hydrocarbon group, X - is OH -, R 12 OH -, R 12 COO - represents, the X - R 12 of a monovalent organic group)
R7〜R11の置換基を有してもよい炭素数1〜10のアルキル基としては、例えば、メチル基、エチル基、n−ブチル基、tert−ブチル基、トリフルオロメチル基、フッ素原子、メトキシ基、t−ブトキシ基、t−ブトキシカルボニルメチルオキシ基等を挙げることができる。なお、R7〜R11は、水素原子、tert−ブチル基であることが好ましい。Examples of the alkyl group having 1 to 10 carbon atoms that may have a substituent of R 7 to R 11 include, for example, a methyl group, an ethyl group, an n-butyl group, a tert-butyl group, a trifluoromethyl group, and a fluorine atom. Methoxy group, t-butoxy group, t-butoxycarbonylmethyloxy group and the like. R 7 to R 11 are preferably a hydrogen atom or a tert-butyl group.
また、X−のR12の1価の有機基としては、例えば、置換基を有してもよいアルキル基、置換基を有してもよいアリール基を挙げることができる。Further, X - as the monovalent organic group R 12, for example, may be mentioned an optionally substituted alkyl group, an aryl group which may have a substituent.
なお、上記X−は、OH−、CH3COO−、以下の式で表される化合物を好適に用いることができる。The above X - is, OH -, CH 3 COO - , can be suitably used a compound represented by the following formula.
上記感光性塩基性化合物の具体例としては、トリフェニルスルホニウム化合物(上記一般式(12−1)で表される化合物)であって、そのアニオン部(X−)がOH−、CH3COO−、または以下の式で表される化合物を好適例として挙げることができる。Specific examples of the photosensitive basic compound include a triphenylsulfonium compound (a compound represented by the above general formula (12-1)), in which an anion portion (X − ) is OH − , CH 3 COO −. Or a compound represented by the following formula can be cited as a preferred example.
なお、上記(c)酸拡散制御剤は、単独でまたは2種以上を混合して使用することができる。 In addition, the said (c) acid diffusion controlling agent can be used individually or in mixture of 2 or more types.
(c)酸拡散制御剤の配合量は、(a)化合物100質量部に対して、15質量部以下であることが好ましく、0.001〜10質量部であることが更に好ましく、0.005〜5質量部であることが特に好ましい。(c)酸拡散制御剤の配合量が15質量部超であると、レジストとしての感度や露光部の現像性が低下するおそれがある。なお、(c)酸拡散制御剤の配合量が0.001質部未満であると、プロセス条件によっては、レジストとしてのパターン形状や寸法忠実度が低下するおそれがある。 (C) The compounding amount of the acid diffusion controller is preferably 15 parts by mass or less, more preferably 0.001 to 10 parts by mass with respect to 100 parts by mass of the compound (a), and 0.005. It is especially preferable that it is -5 mass parts. (C) If the blending amount of the acid diffusion controller is more than 15 parts by mass, the sensitivity as a resist and the developability of the exposed part may be lowered. Note that if the amount of the (c) acid diffusion controller is less than 0.001 parts by mass, the pattern shape and dimensional fidelity as a resist may be lowered depending on the process conditions.
[2−3]その他の成分:
本発明の感放射線性組成物は、上記(a)化合物、(b)感放射線性酸発生剤、及び(c)酸拡散制御剤を、溶剤に溶解させたものであることが好ましい。すなわち、その他の成分として溶剤を含有することが好ましい。また、本発明の感放射線性組成物には、必要に応じて、その他の成分として、界面活性剤、増感剤、脂肪族添加剤等の各種の添加剤を配合することができる。[2-3] Other components:
The radiation sensitive composition of the present invention is preferably prepared by dissolving the compound (a), (b) a radiation sensitive acid generator, and (c) an acid diffusion controller in a solvent. That is, it is preferable to contain a solvent as another component. Moreover, various additives, such as surfactant, a sensitizer, and an aliphatic additive, can be mix | blended with the radiation sensitive composition of this invention as other components as needed.
上記溶剤としては、プロピレングリコールモノメチルエーテルアセテート、2−ヘプタノン及びシクロヘキサノンの群から選ばれる少なくとも1種(以下、「溶剤1」という)が好ましい。溶剤としては上記の溶剤1以外の溶剤(以下、「他の溶剤」という)を使用することもできる。なお、溶剤1と他の溶剤を混合して用いることもできる。 The solvent is preferably at least one selected from the group of propylene glycol monomethyl ether acetate, 2-heptanone and cyclohexanone (hereinafter referred to as “solvent 1”). As the solvent, a solvent other than the above-described solvent 1 (hereinafter referred to as “other solvent”) can also be used. In addition, the solvent 1 and another solvent can also be mixed and used.
他の溶剤としては、例えば、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−n−プロピルエーテルアセテート、プロピレングリコールモノ−i−プロピルエーテルアセテート、プロピレングリコールモノ−n−ブチルエーテルアセテート、プロピレングリコールモノ−i−ブチルエーテルアセテート、プロピレングリコールモノ−sec−ブチルエーテルアセテート、プロピレングリコールモノ−t−ブチルエーテルアセテート等のプロピレングリコールモノアルキルエーテルアセテート類; Examples of other solvents include propylene glycol monoethyl ether acetate, propylene glycol mono-n-propyl ether acetate, propylene glycol mono-i-propyl ether acetate, propylene glycol mono-n-butyl ether acetate, propylene glycol mono-i- Propylene glycol monoalkyl ether acetates such as butyl ether acetate, propylene glycol mono-sec-butyl ether acetate, propylene glycol mono-t-butyl ether acetate;
2−ブタノン、2−ペンタノン、3−メチル−2−ブタノン、2−ヘキサノン、4−メチル−2−ペンタノン、3−メチル−2−ペンタノン、3,3−ジメチル−2−ブタノン、2−オクタノン等の直鎖状若しくは分岐状のケトン類;シクロペンタノン、3−メチルシクロペンタノン、2−メチルシクロヘキサノン、2,6−ジメチルシクロヘキサノン、イソホロン等の環状のケトン類;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、2−ヒドロキシプロピオン酸n−プロピル、2−ヒドロキシプロピオン酸i−プロピル、2−ヒドロキシプロピオン酸n−ブチル、2−ヒドロキシプロピオン酸i−ブチル、2−ヒドロキシプロピオン酸sec−ブチル、2−ヒドロキシプロピオン酸t−ブチル等の2−ヒドロキシプロピオン酸アルキル類;3−メトキシプロピオン酸メチル、3−メトキシプロピオン酸エチル、3−エ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等の3−アルコキシプロピオン酸アルキル類のほか、 2-butanone, 2-pentanone, 3-methyl-2-butanone, 2-hexanone, 4-methyl-2-pentanone, 3-methyl-2-pentanone, 3,3-dimethyl-2-butanone, 2-octanone, etc. Linear or branched ketones; cyclic ketones such as cyclopentanone, 3-methylcyclopentanone, 2-methylcyclohexanone, 2,6-dimethylcyclohexanone, isophorone; methyl 2-hydroxypropionate, 2 -Ethyl hydroxypropionate, n-propyl 2-hydroxypropionate, i-propyl 2-hydroxypropionate, n-butyl 2-hydroxypropionate, i-butyl 2-hydroxypropionate, sec-butyl 2-hydroxypropionate 2-hydroxypropionate t-butyl 2-hydroxy Propionate alkyls; methyl 3-methoxy propionate, 3-methoxy ethyl propionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate and the like of 3-alkoxy propionic acid alkyl ethers other,
n−プロピルアルコール、i−プロピルアルコール、n−ブチルアルコール、t−ブチルアルコール、シクロヘキサノール、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、エチレングリコールモノ−n−プロピルエーテル、エチレングリコールモノ−n−ブチルエーテル、ジエチ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エチルエーテル、ジエチレングリコールジ−n−プロピルエーテル、ジエチレングリコールジ−n−ブチルエーテル、エチ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−n−プロピルエーテルアセテート、プロピレングリコールモノメチルエーテル、プロピ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−n−プロピルエーテル、 n-propyl alcohol, i-propyl alcohol, n-butyl alcohol, t-butyl alcohol, cyclohexanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether , Diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol di-n-propyl ether, diethylene glycol di-n-butyl ether, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol mono-n-propyl ether acetate, propylene glycol monomethyl ether , Propylene glycol monoethyl Ether, propylene glycol mono -n- propyl ether,
トルエン、キシレン、2−ヒドロキシ−2−メチルプロピオン酸エチル、エトキシ酢酸エチル、ヒドロキシ酢酸エチル、2−ヒドロキシ−3−メチル酪酸メチル、3−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−メチル−3−メトキシブチルプロピオネート、3−メチル−3−メトキシブチルブチレート、酢酸エチル、酢酸n−プロピル、酢酸n−ブチル、アセト酢酸メチル、アセト酢酸エチル、ピルビン酸メチル、ピルビン酸エチル、N−メチルピロリドン、N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド、ベンジルエチルエーテル、ジ−n−ヘキシルエーテル、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、カプロン酸、カプリル酸、1−オクタノール、1−ノナノール、ベンジルアルコール、酢酸ベンジル、安息香酸エチル、しゅう酸ジエチル、マレイン酸ジエチル、γ−ブチロラクトン、炭酸エチレン、炭酸プロピレン等を挙げることができる。 Toluene, xylene, ethyl 2-hydroxy-2-methylpropionate, ethyl ethoxyacetate, ethyl hydroxyacetate, methyl 2-hydroxy-3-methylbutyrate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, 3 -Methyl-3-methoxybutyl propionate, 3-methyl-3-methoxybutyl butyrate, ethyl acetate, n-propyl acetate, n-butyl acetate, methyl acetoacetate, ethyl acetoacetate, methyl pyruvate, ethyl pyruvate N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, benzyl ethyl ether, di-n-hexyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, caproic acid, caprylic acid, 1-o Pentanol, 1-nonanol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethyl oxalate, diethyl maleate, .gamma.-butyrolactone, ethylene carbonate, and propylene carbonate.
これらの他の溶剤のうち、直鎖状若しくは分岐状のケトン類、環状のケトン類、プロピレングリコールモノアルキルエーテルアセテート類、2−ヒドロキシプロピオン酸アルキル類、3−アルコキシプロピオン酸アルキル類、γ−ブチロラクトン等が好ましい。上記他の溶剤は、単独でまたは2種以上を混合して使用することができる。 Among these other solvents, linear or branched ketones, cyclic ketones, propylene glycol monoalkyl ether acetates, alkyl 2-hydroxypropionate, alkyl 3-alkoxypropionate, γ-butyrolactone Etc. are preferred. These other solvents can be used alone or in admixture of two or more.
溶剤として、溶剤1と他の溶剤との混合溶剤を使用する場合、他の溶剤の割合は、全溶剤に対して、50質量%以下であることが好ましく、40質量%以下であることが更に好ましく、30質量%以下であることが特に好ましい。 When using the mixed solvent of the solvent 1 and another solvent as a solvent, it is preferable that the ratio of another solvent is 50 mass% or less with respect to all the solvents, and it is further 40 mass% or less. It is preferably 30% by mass or less.
本発明の感放射線性組成物は、普通、その使用に際して、全固形分濃度が、1〜50質量%であることが好ましく、1〜25質量%であることが更に好ましい。そして、(a)化合物、(b)感放射線性酸発生剤、(c)酸拡散制御剤、及び、必要によりその他の添加物(溶剤を除く)を、上記全固形分濃度となるように、溶剤に溶解して均一溶液とした後、好ましくは、例えば孔径0.2μm程度のフィルターでろ過して感放射線性組成物からなる組成物溶液を得ることができる。 In general, the radiation-sensitive composition of the present invention preferably has a total solid content of 1 to 50% by mass, and more preferably 1 to 25% by mass. And (a) a compound, (b) a radiation sensitive acid generator, (c) an acid diffusion control agent, and other additives (excluding the solvent) as necessary, so that the total solid content concentration is obtained. After dissolving in a solvent to obtain a uniform solution, it is preferable to obtain a composition solution composed of a radiation-sensitive composition by, for example, filtering with a filter having a pore size of about 0.2 μm.
なお、その他の成分として含有される界面活性剤は、塗布性、ストリエーション、現像性等を改良する作用を示す成分である。このような界面活性剤としては、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オレイルエーテル、ポリオキシエチレンn−オクチルフェニルエーテル、ポリオキシエチレンn−ノニルフェニルエーテル、ポリエチレングリコールジラウレート、ポリエチレングリコールジステアレート等のノニオン系界面活性剤のほか、以下商品名で、KP341(信越化学工業社製)、ポリフローNo.75,同No.95(共栄社化学社製)、エフトップEF301,同EF303,同EF352(トーケムプロダクツ社製)、メガファックスF171,同F173(大日本インキ化学工業社製)、フロラードFC430,同FC431(住友スリーエム社製)、アサヒガードAG710,サーフロンS−382,同SC−101,同SC−102,同SC−103,同SC−104,同SC−105,同SC−106(旭硝子社製)等を挙げることができる。これらの界面活性剤は、一種単独でもまたは2種以上を混合しても使用することができる。 In addition, the surfactant contained as other components is a component having an effect of improving coatability, striation, developability and the like. Examples of such surfactants include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene n-octylphenyl ether, polyoxyethylene n-nonylphenyl ether, and polyethylene glycol dilaurate. In addition to nonionic surfactants such as polyethylene glycol distearate, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), Polyflow No. 75, no. 95 (manufactured by Kyoeisha Chemical Co., Ltd.), F-top EF301, EF303, EF352 (manufactured by Tochem Products), Megafax F171, F173 (manufactured by Dainippon Ink & Chemicals), Florard FC430, FC431 (Sumitomo 3M) Asahi Guard AG710, Surflon S-382, SC-101, SC-102, SC-103, SC-104, SC-105, SC-106 (Asahi Glass Co., Ltd.), etc. Can do. These surfactants can be used singly or in combination of two or more.
界面活性剤は、単独でまたは2種以上を混合して使用することができる。界面活性剤の配合量は、(a)化合物100質量部に対して、0.001〜2質量部であることが好ましい。 Surfactant can be used individually or in mixture of 2 or more types. It is preferable that the compounding quantity of surfactant is 0.001-2 mass parts with respect to 100 mass parts of (a) compounds.
上記増感剤は、放射線のエネルギーを吸収して、そのエネルギーを(b)感放射線性酸発生剤に伝達し、それにより酸の生成量を増加する作用を示すもので、感放射線性組成物のみかけの感度を向上させる効果を有する。このような増感剤としては、カルバゾール類、アセトフェノン類、ベンゾフェノン類、ナフタレン類、フェノール類、ビアセチル、エオシン、ローズベンガル、ピレン類、アントラセン類、フェノチアジン類等を挙げることができる。なお、これらの増感剤は、単独でまたは2種以上を混合して使用することができる。増感剤の配合量は、(a)化合物100質量部に対して、0.1〜10質量部であることが好ましい。 The sensitizer absorbs radiation energy and transmits the energy to (b) the radiation-sensitive acid generator, thereby increasing the amount of acid produced. The radiation-sensitive composition It has the effect of improving the apparent sensitivity. Examples of such sensitizers include carbazoles, acetophenones, benzophenones, naphthalenes, phenols, biacetyl, eosin, rose bengal, pyrenes, anthracenes, phenothiazines, and the like. In addition, these sensitizers can be used individually or in mixture of 2 or more types. It is preferable that the compounding quantity of a sensitizer is 0.1-10 mass parts with respect to 100 mass parts of (a) compounds.
また、染料または顔料を配合することにより、露光部の潜像を可視化させて、露光時のハレーションの影響を緩和できる。接着助剤を配合することにより、基板との接着性を改善することができる。 Further, by blending a dye or pigment, the latent image in the exposed area can be visualized, and the influence of halation during exposure can be reduced. By blending an adhesion aid, the adhesion to the substrate can be improved.
また、本発明の感放射線性組成物には、酸解離性基を有する脂環族添加剤や酸解離性基を有しない脂環族添加剤を添加することができる。酸解離性基を有する脂環族添加剤や酸解離性基を有しない脂環族添加剤は、ドライエッチング耐性、パターン形状、基板との接着性等を更に改善する作用を有する成分である。 Moreover, the alicyclic additive which has an acid dissociable group, and the alicyclic additive which does not have an acid dissociable group can be added to the radiation sensitive composition of this invention. An alicyclic additive having an acid dissociable group or an alicyclic additive not having an acid dissociable group is a component having an action of further improving dry etching resistance, pattern shape, adhesion to a substrate, and the like.
このような脂環族添加剤としては、例えば、1−アダマンタンカルボン酸、2−アダマンタノン、1−アダマンタンカルボン酸t−ブチル、1−アダマンタンカルボン酸t−ブトキシカルボニルメチル、1−アダマンタンカルボン酸α−ブチロラクトンエステル、1,3−アダマンタンジカルボン酸ジ−t−ブチル、1−アダマンタン酢酸t−ブチル、1−アダマンタン酢酸t−ブトキシカルボニルメチル、1,3−アダマンタンジ酢酸ジ−t−ブチル、2,5−ジメチル−2,5−ジ(アダマンチルカルボニルオキシ)ヘキサン等のアダマンタン誘導体類;デオキシコール酸t−ブチル、デオキシコール酸t−ブトキシカルボニルメチル、デオキシコール酸2−エトキシエチル、デオキシコール酸2−シクロヘキシルオキシエチル、デオキシコール酸3−オキソシクロヘキシル、デオキシコール酸テトラヒドロピラニル、デオキシコール酸メバロノラクトンエステル等のデオキシコール酸エステル類;リトコール酸t−ブチル、リトコール酸t−ブトキシカルボニルメチル、リトコール酸2−エトキシエチル、リトコール酸2−シクロヘキシルオキシエチル、リトコール酸3−オキソシクロヘキシル、リトコール酸テトラヒドロピラニル、リトコール酸メバロノラクトンエステル等のリトコール酸エステル類;アジピン酸ジメチル、アジピン酸ジエチル、アジピン酸ジプロピル、アジピン酸ジn−ブチル、アジピン酸ジt−ブチル等のアルキルカルボン酸エステル類や、3−〔2−ヒドロキシ−2,2−ビス(トリフルオロメチル)エチル〕テトラシクロ[4.4.0.12,5.17,10]ドデカン等を挙げることができる。Examples of such alicyclic additives include 1-adamantanecarboxylic acid, 2-adamantanone, 1-adamantanecarboxylic acid t-butyl, 1-adamantanecarboxylic acid t-butoxycarbonylmethyl, 1-adamantanecarboxylic acid α. -Butyrolactone ester, 1,3-adamantane dicarboxylic acid di-t-butyl, 1-adamantane acetate t-butyl, 1-adamantane acetate t-butoxycarbonylmethyl, 1,3-adamantane diacetate di-t-butyl, 2, Adamantane derivatives such as 5-dimethyl-2,5-di (adamantylcarbonyloxy) hexane; t-butyl deoxycholic acid, t-butoxycarbonylmethyl deoxycholic acid, 2-ethoxyethyl deoxycholic acid, 2-deoxycholic acid 2- Cyclohexyloxyethyl, deoxy Deoxycholic acid esters such as 3-oxocyclohexyl cholic acid, tetrahydropyranyl deoxycholic acid, mevalonolactone ester of deoxycholic acid; t-butyl lithocholic acid, t-butoxycarbonylmethyl lithocholic acid, 2-ethoxyethyl lithocholic acid, Lithocholic acid esters such as 2-cyclohexyloxyethyl lithocholic acid, 3-oxocyclohexyl lithocholic acid, tetrahydropyranyl lithocholic acid, mevalonolactone ester of lithocholic acid; dimethyl adipate, diethyl adipate, dipropyl adipate, din adipate - butyl, alkyl carboxylic acid esters such as adipate t- butyl or 3- [2-hydroxy-2,2-bis (trifluoromethyl) ethyl] tetracyclo [4.4.0.1 2, 5 1 7,10 ] dodecane and the like.
これらの脂環族添加剤は、単独でまたは2種以上を混合して使用できる。脂環族添加剤の配合量は、(a)化合物100質量部に対して、0.5〜20質量部であることが好ましい。脂環族添加剤の配合量が20質量部超であると、レジストとしての耐熱性が低下するおそれがある。 These alicyclic additives can be used alone or in admixture of two or more. It is preferable that the compounding quantity of an alicyclic additive is 0.5-20 mass parts with respect to 100 mass parts of (a) compounds. There exists a possibility that the heat resistance as a resist may fall that the compounding quantity of an alicyclic additive exceeds 20 mass parts.
更に、上記以外の添加剤としては、アルカリ可溶性樹脂、酸解離性の保護基を有する低分子のアルカリ溶解性制御剤、ハレーション防止剤、保存安定化剤、消泡剤等を挙げることができる。 Furthermore, examples of additives other than the above include alkali-soluble resins, low-molecular alkali solubility control agents having an acid-dissociable protecting group, antihalation agents, storage stabilizers, antifoaming agents, and the like.
[3]レジストパターンの形成方法:
本発明の感放射線性組成物は、特に化学増幅型レジストとして有用である。上記化学増幅型レジストにおいては、露光により(b)感放射線性酸発生剤から発生した酸の作用によって、(a)化合物の酸解離性基が脱離して、アルカリ可溶性部位を生じ、その結果、レジストの露光部のアルカリ現像液に対する溶解性が高くなり、この露光部がアルカリ現像液によって溶解、除去され、ポジ型のレジストパターンが得られる。[3] Method for forming resist pattern:
The radiation-sensitive composition of the present invention is particularly useful as a chemically amplified resist. In the above chemically amplified resist, (b) the acid-dissociable group of the compound is eliminated by the action of the acid generated from the radiation-sensitive acid generator by exposure, and an alkali-soluble site is generated. The solubility of the exposed portion of the resist in the alkaline developer is increased, and the exposed portion is dissolved and removed by the alkaline developer to obtain a positive resist pattern.
本発明の感放射線性組成物によりレジストパターンを形成する際には、上述した組成物溶液を、回転塗布、流延塗布、ロール塗布等の適宜の塗布手段によって、例えば、シリコンウエハー、アルミニウムで被覆されたウエハー等の基板上に塗布することにより、レジスト被膜を形成し、場合により予め加熱処理(以下、「PB」という)を行った後、所定のレジストパターンを形成するようにこのレジスト被膜に露光する。その際に使用される放射線としては、例えば、KrFエキシマレーザー(波長248nm)、EUV(極紫外線、波長13nm等)等の遠紫外線、シンクロトロン放射線等のX線、電子線等の荷電粒子線等を適宜選択して使用することができる。また、露光量等の露光条件は、感放射線性組成物の配合組成や添加剤の種類等に応じて適宜選定され、液浸露光でも構わない。 When forming a resist pattern with the radiation-sensitive composition of the present invention, the above-described composition solution is coated with, for example, a silicon wafer or aluminum by an appropriate application means such as spin coating, cast coating or roll coating. A resist film is formed by coating on a substrate such as a wafer, and in some cases, a heat treatment (hereinafter referred to as “PB”) is performed in advance, and then a predetermined resist pattern is formed on the resist film. Exposure. Examples of radiation used at that time include far ultraviolet rays such as KrF excimer laser (wavelength 248 nm), EUV (extreme ultraviolet rays, wavelength 13 nm, etc.), X-rays such as synchrotron radiation, and charged particle beams such as electron beams. Can be appropriately selected and used. Further, the exposure conditions such as the exposure amount are appropriately selected according to the composition of the radiation-sensitive composition, the kind of additive, and the like, and may be immersion exposure.
本発明においては、露光後に加熱処理(以下、「PEB」という)を行うことが好ましい。このPEBにより、(a)化合物の酸解離性基の脱離を円滑に進行させることが可能となる。PEBの加熱条件は、感放射線性組成物の配合組成によって変わるが、30〜200℃であることが好ましく、50〜170℃であることが更に好ましい。 In the present invention, it is preferable to perform heat treatment (hereinafter referred to as “PEB”) after exposure. This PEB makes it possible to smoothly proceed with elimination of the acid dissociable group of the compound (a). The heating conditions for PEB vary depending on the composition of the radiation-sensitive composition, but are preferably 30 to 200 ° C, and more preferably 50 to 170 ° C.
本発明においては、感放射線性組成物の潜在能力を最大限に引き出すため、例えば特公平6−12452号公報等に開示されているように、使用される基板上に有機系あるいは無機系の反射防止膜を形成しておくこともできる。また、環境雰囲気中に含まれる塩基性不純物等の影響を防止するため、例えば特開平5−188598号公報等に開示されているように、レジスト被膜上に保護膜を設けることもできる。または、これらの技術を併用することもできる。 In the present invention, in order to maximize the potential of the radiation-sensitive composition, as disclosed in, for example, Japanese Patent Publication No. 6-12452, an organic or inorganic reflective material is used. A prevention film can also be formed. Further, in order to prevent the influence of basic impurities contained in the environmental atmosphere, a protective film can be provided on the resist film as disclosed in, for example, JP-A-5-188598. Or these techniques can also be used together.
次いで、露光されたレジスト被膜を現像することにより、所定のレジストパターンを形成する。現像に使用される現像液としては、例えば、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、けい酸ナトリウム、メタけい酸ナトリウム、アンモニア水、エチルアミン、n−プロピルアミン、ジエチルアミン、ジ−n−プロピルアミン、トリエチルアミン、メチルジエチルアミン、エチルジメチルアミン、トリエタノールアミン、テトラメチルアンモニウムヒドロキシド、ピロール、ピペリジン、コリン、1,8−ジアザビシクロ−[5.4.0]−7−ウンデセン、1,5−ジアザビシクロ−[4.3.0]−5−ノネン等のアルカリ性化合物の少なくとも一種を溶解したアルカリ性水溶液が好ましい。 Next, the exposed resist film is developed to form a predetermined resist pattern. Examples of the developer used for development include sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, aqueous ammonia, ethylamine, n-propylamine, diethylamine, and di-n-propylamine. , Triethylamine, methyldiethylamine, ethyldimethylamine, triethanolamine, tetramethylammonium hydroxide, pyrrole, piperidine, choline, 1,8-diazabicyclo- [5.4.0] -7-undecene, 1,5-diazabicyclo- An alkaline aqueous solution in which at least one of alkaline compounds such as [4.3.0] -5-nonene is dissolved is preferable.
上記アルカリ性水溶液の濃度は、10質量%以下であることが好ましい。アルカリ性水溶液の濃度が10質量%超であると、非露光部も現像液に溶解するおそれがある。また、現像液は、pH8〜14であることが好ましく、pH9〜14であることが更に好ましい。 The concentration of the alkaline aqueous solution is preferably 10% by mass or less. If the concentration of the alkaline aqueous solution is more than 10% by mass, the unexposed area may be dissolved in the developer. Further, the developer is preferably pH 8 to 14, and more preferably pH 9 to 14.
また、上記アルカリ性水溶液からなる現像液には、例えば有機溶媒を添加することもできる。上記有機溶媒としては、例えば、アセトン、メチルエチルケトン、メチルi−ブチルケトン、シクロペンタノン、シクロヘキサノン、3−メチルシクロペンタノン、2,6−ジメチルシクロヘキサノン等のケトン類;メチルアルコール、エチルアルコール、n−プロピルアルコール、i−プロピルアルコール、n−ブチルアルコール、t−ブチルアルコール、シクロペンタノール、シクロヘキサノール、1,4−ヘキサンジオール、1,4−ヘキサンジメチロール等のアルコール類;テトラヒドロフラン、ジオキサン等のエーテル類;酢酸エチル、酢酸n−ブチル、酢酸i−アミル等のエステル類;トルエン、キシレン等の芳香族炭化水素類や、フェノール、アセトニルアセトン、ジメチルホルムアミド等を挙げることができる。これらの有機溶媒は、単独でまたは2種以上を混合して使用することができる。 Further, for example, an organic solvent can be added to the developer composed of the alkaline aqueous solution. Examples of the organic solvent include ketones such as acetone, methyl ethyl ketone, methyl i-butyl ketone, cyclopentanone, cyclohexanone, 3-methylcyclopentanone, and 2,6-dimethylcyclohexanone; methyl alcohol, ethyl alcohol, and n-propyl. Alcohols such as alcohol, i-propyl alcohol, n-butyl alcohol, t-butyl alcohol, cyclopentanol, cyclohexanol, 1,4-hexanediol, 1,4-hexanedimethylol; ethers such as tetrahydrofuran and dioxane Esters such as ethyl acetate, n-butyl acetate and i-amyl acetate; aromatic hydrocarbons such as toluene and xylene; phenol, acetonylacetone and dimethylformamide. These organic solvents can be used alone or in admixture of two or more.
有機溶媒の使用量は、アルカリ性水溶液100体積部に対して、100体積部以下が好ましい。有機溶媒の使用量が100体積部超であると、現像性が低下して、露光部の現像残りが多くなるおそれがある。また、アルカリ性水溶液からなる現像液には、界面活性剤等を適量添加することもできる。なお、アルカリ性水溶液からなる現像液で現像した後、水で洗浄して乾燥することもできる。 The amount of the organic solvent used is preferably 100 parts by volume or less with respect to 100 parts by volume of the alkaline aqueous solution. If the amount of the organic solvent used is more than 100 parts by volume, the developability is lowered, and there is a possibility that the remaining development in the exposed part increases. In addition, an appropriate amount of a surfactant or the like can be added to the developer composed of an alkaline aqueous solution. In addition, after developing with the developing solution which consists of alkaline aqueous solution, it can also wash with water and can be dried.
以下、本発明を実施例に基づいて具体的に説明するが、本発明はこれらの実施例に限定されるものではない。なお、実施例、比較例中の「部」及び「%」は、特に断らない限り質量基準である。 EXAMPLES Hereinafter, although this invention is demonstrated concretely based on an Example, this invention is not limited to these Examples. In the examples and comparative examples, “parts” and “%” are based on mass unless otherwise specified.
(実施例1)化合物(A−1):
レゾルシノール2.20gと、2,5−ジメトキシテトラヒドロフラン0.79gとを、エタノール6mLに添加し、12Nの塩酸2mlを加え、80℃で24時間加熱した後、反応液をメタノールに注いで固体を得、この固体を約200mlのメタノールで洗浄し、真空下60℃、24時間の条件で乾燥することにより、収率29%で下記構造の淡黄色固体(S)を得た。得られた固体のMnは9500、Mw/Mnは2.1であった。Example 1 Compound (A-1):
2.20 g of resorcinol and 0.79 g of 2,5-dimethoxytetrahydrofuran are added to 6 mL of ethanol, 2 ml of 12N hydrochloric acid is added, and the mixture is heated at 80 ° C. for 24 hours, and then the reaction solution is poured into methanol to obtain a solid. The solid was washed with about 200 ml of methanol and dried under vacuum at 60 ° C. for 24 hours to obtain a light yellow solid (S) having the following structure in a yield of 29%. The obtained solid Mn was 9500, and Mw / Mn was 2.1.
得られた淡黄色固体(S)のMALDI−TOF−MS(型番SHIMAZU/KRATOSマトリックス支援レーザーイオン化飛行時間型質量分析装置 KOMPACT MALDI IV tDE、島津製作所社製)分析の結果から、ポリマー鎖中に環状オリゴマーであるカリックス[4]レゾルシンアレーンの繰り返し単位を有する化合物であると同定された。 From the result of MALDI-TOF-MS (model number SHIMAZU / KRATOS matrix-assisted laser ionization time-of-flight mass spectrometer KOMPACT MALDI IV tDE, manufactured by Shimadzu Corporation) of the obtained pale yellow solid (S), it was cyclic in the polymer chain. It was identified as a compound having a repeating unit of calix [4] resorcinarene which is an oligomer.
得られた上記淡黄色固体(S)1g、テトラブチルアンモニウムブロミド(TBAB)0.25gにピリジン50gを加え撹拌した後、ジ−tert−ブチルジカーボナート(DiBoc)2.0gをゆっくり滴下し、室温で6時間撹拌した。反応が終了した後、母液をクロロホルムで希釈し、1Nの塩酸によって3回および水で2回洗浄し、有機層を無水硫酸マグネシウムよりなる乾燥剤を用いて乾燥させ、乾燥剤をろ別した後に有機層を濃縮し、良溶媒にクロロホルム、貧溶媒にn−ヘキサンを用いて再沈精製することによって、固体を得た。収率50%であった。なお、1H−NMR分析を行ったところ下記化合物(A−1)における保護率(化合物(1)中のフェノール性水酸基の水素原子がt−ブトキシカルボニル基で置換された割合)は50%であった。After adding 50 g of pyridine to 1 g of the obtained pale yellow solid (S) and 0.25 g of tetrabutylammonium bromide (TBAB) and stirring, 2.0 g of di-tert-butyl dicarbonate (DiBoc) was slowly added dropwise. Stir at room temperature for 6 hours. After completion of the reaction, the mother liquor was diluted with chloroform, washed 3 times with 1N hydrochloric acid and twice with water, the organic layer was dried using a desiccant composed of anhydrous magnesium sulfate, and the desiccant was filtered off. The organic layer was concentrated and purified by reprecipitation using chloroform as a good solvent and n-hexane as a poor solvent to obtain a solid. The yield was 50%. As a result of 1 H-NMR analysis, the protection ratio (ratio in which the hydrogen atom of the phenolic hydroxyl group in compound (1) was substituted with a t-butoxycarbonyl group) in the following compound (A-1) was 50%. there were.
(実施例2)化合物A−2の合成:
得られた上記淡黄色固体(S)1g、テトラブチルアンモニウムブロマイド0.25gを加え、1−メチル−2−ピロリドン10gを加えた後、70℃で1時間攪拌した。その後、炭酸カリウム1.2gを加え、70℃で1時間撹拌した。その後、1−メチル−2−ピロリドン3gに溶かしたブロモ酢酸t−ブチル1.8gを徐々に加え、60℃で6時間攪拌した。室温まで冷却後、水/塩化メチレンで抽出を行い、続いて、3wt%シュウ酸水溶液100mlで2回洗浄した後、100mlで2回洗浄した。水層を廃棄したのち、有機層を硫酸マグネシウムで乾燥させた。乾燥剤をろ別した後に有機層を濃縮し、良溶媒にクロロホルム、貧溶媒にn−ヘキサンを用いて再沈精製することによって、固体を得た。収率55%であった。なお、1H−NMR分析を行ったところ下記化合物(A−2)における保護率(化合物(1)中のフェノール性水酸基の水素原子がtert−ブトキシカルボニルメチル基で置換された割合)は50%であった。Example 2 Synthesis of Compound A-2:
1 g of the obtained pale yellow solid (S) and 0.25 g of tetrabutylammonium bromide were added, 10 g of 1-methyl-2-pyrrolidone was added, and the mixture was stirred at 70 ° C. for 1 hour. Thereafter, 1.2 g of potassium carbonate was added and stirred at 70 ° C. for 1 hour. Thereafter, 1.8 g of t-butyl bromoacetate dissolved in 3 g of 1-methyl-2-pyrrolidone was gradually added and stirred at 60 ° C. for 6 hours. After cooling to room temperature, extraction with water / methylene chloride was performed, followed by washing twice with 100 ml of a 3 wt% oxalic acid aqueous solution and then twice with 100 ml. After discarding the aqueous layer, the organic layer was dried over magnesium sulfate. After filtering off the desiccant, the organic layer was concentrated and purified by reprecipitation using chloroform as a good solvent and n-hexane as a poor solvent to obtain a solid. The yield was 55%. As a result of 1 H-NMR analysis, the following compound (A-2) had a protection rate of 50% (the ratio in which the hydrogen atom of the phenolic hydroxyl group in compound (1) was replaced with a tert-butoxycarbonylmethyl group). Met.
(実施例3)化合物A−3の合成:
得られた上記淡黄色固体(S)1g、テトラブチルアンモニウムブロマイド0.25gを加え、1−メチル−2−ピロリドン10gを加えた後、70℃で1時間攪拌した。その後、炭酸カリウム1.2gを加え、70℃で1時間撹拌した。その後、1−メチル−2−ピロリドン3gに溶かしたブロモ酢酸2−メチル−2−アダマンチル2.6gを徐々に加え、60℃で6時間攪拌した。室温まで冷却後、水/塩化メチレンで抽出を行い、続いて、3wt%シュウ酸水溶液100mlで2回洗浄した後、100mlで2回洗浄した。水層を廃棄したのち、有機層を硫酸マグネシウムで乾燥させた。乾燥剤をろ別した後に有機層を濃縮し、良溶媒にクロロホルム、貧溶媒にn−ヘキサンを用いて再沈精製することによって、固体を得た。収率55%であった。なお、1H−NMR分析を行ったところ下記化合物(A−2)における保護率(化合物(1)中のフェノール性水酸基の水素原子が2−メチル−2−アダマンチルオキシカルボニルメチル基で置換された割合)は50%であった。Example 3 Synthesis of Compound A-3:
1 g of the obtained pale yellow solid (S) and 0.25 g of tetrabutylammonium bromide were added, 10 g of 1-methyl-2-pyrrolidone was added, and the mixture was stirred at 70 ° C. for 1 hour. Thereafter, 1.2 g of potassium carbonate was added and stirred at 70 ° C. for 1 hour. Thereafter, 2.6 g of 2-methyl-2-adamantyl bromoacetate dissolved in 3 g of 1-methyl-2-pyrrolidone was gradually added and stirred at 60 ° C. for 6 hours. After cooling to room temperature, extraction with water / methylene chloride was performed, followed by washing twice with 100 ml of a 3 wt% oxalic acid aqueous solution and then twice with 100 ml. After discarding the aqueous layer, the organic layer was dried over magnesium sulfate. After filtering off the desiccant, the organic layer was concentrated and purified by reprecipitation using chloroform as a good solvent and n-hexane as a poor solvent to obtain a solid. The yield was 55%. As a result of 1 H-NMR analysis, the protection rate in the following compound (A-2) (the hydrogen atom of the phenolic hydroxyl group in compound (1) was substituted with a 2-methyl-2-adamantyloxycarbonylmethyl group) The ratio) was 50%.
比較合成例1 酸解離性基含有樹脂(A−4):
ポリヒドロキシスチレン(VP8000、日本曹達社製(Mw9000、Mw/Mn=1.1)10gの酢酸ブチル20%溶液に、ジ−t−ブチル−ジ−カーボナート5.50g、トリエチルアミン2.80gをゆっくり滴下し、この反応液を60℃で7時間攪拌した。その後、上記反応液に多量の水を加え、再沈精製を繰り返した。続いて、減圧乾燥を行い、ヒドロキシ基が30%t−ブトキシカルボニルで保護されたポリヒドロキシスチレン(A−4)12.0gを得た。Comparative Synthesis Example 1 Acid-dissociable group-containing resin (A-4):
Polyhydroxystyrene (VP8000, Nippon Soda Co., Ltd. (Mw9000, Mw / Mn = 1.1) 10 g of butyl acetate in 20% solution was slowly added dropwise with di-t-butyl-di-carbonate 5.50 g and triethylamine 2.80 g. The reaction solution was stirred for 7 hours at 60 ° C. Thereafter, a large amount of water was added to the reaction solution, and reprecipitation purification was repeated, followed by drying under reduced pressure, whereby the hydroxy group was 30% t-butoxycarbonyl. 12.0 g of polyhydroxystyrene (A-4) protected with 1 was obtained.
(実施例4)
化合物(A−1)100部、(b)感放射線性酸発生剤としてトリフェニルスルホニウムトリフルオロメタンスルホネート(表1中、「B−1」と示す)9部、(c)酸拡散制御剤としてトリ−n−オクチルアミン(表1中、「C−1」と示す)0.3部、溶剤として乳酸エチル(表1中、「D−1」と示す)600部、及びプロピレングリコールモノメチルエーテルアセテート(表1中、「D−3」と示す)1500部を混合し、この混合液を孔径200nmのメンブランフィルターでろ過して組成物溶液(感放射線性組成物)を得た。Example 4
100 parts of compound (A-1), (b) 9 parts of triphenylsulfonium trifluoromethanesulfonate (shown as “B-1” in Table 1) as a radiation sensitive acid generator, and (c) trimethyl as an acid diffusion controller. -N-octylamine (shown as "C-1" in Table 1) 0.3 part, ethyl lactate (shown as "D-1" in Table 1) 600 parts as a solvent, and propylene glycol monomethyl ether acetate ( 1500 parts (shown as “D-3” in Table 1) were mixed, and this mixed solution was filtered through a membrane filter having a pore size of 200 nm to obtain a composition solution (radiation sensitive composition).
次いで、東京エレクトロン社製のクリーントラックACT−8内で、シリコンウエハー上に上記組成物溶液をスピンコートした後、90℃で90秒間PB(加熱処理)を行い、膜厚100nmのレジスト(感放射線性組成物)被膜を形成した。その後、簡易型の電子線描画装置(日立製作所社製、型式「HL800D」、出力;50KeV、電流密度;5.0アンペア/cm2)を用いてレジスト被膜に電子線を照射した。電子線の照射後、90℃で90秒間PEBを行った。その後、2.38%テトラメチルアンモニウムヒドロキシド水溶液を用い、23℃で1分間、パドル法により現像した後、純水で水洗し、乾燥して、レジストパターンを形成した。このようにして形成したレジストについて下記の要領で評価を実施した。Next, in the clean track ACT-8 manufactured by Tokyo Electron Co., Ltd., the above composition solution was spin-coated on a silicon wafer, followed by PB (heat treatment) at 90 ° C. for 90 seconds to form a resist having a film thickness of 100 nm (radiation sensitive). Composition) A film was formed. Thereafter, the resist film was irradiated with an electron beam using a simple electron beam drawing apparatus (manufactured by Hitachi, Ltd., model “HL800D”, output: 50 KeV, current density: 5.0 amperes / cm 2 ). After the electron beam irradiation, PEB was performed at 90 ° C. for 90 seconds. Thereafter, using a 2.38% tetramethylammonium hydroxide aqueous solution, development was carried out at 23 ° C. for 1 minute by the paddle method, followed by washing with pure water and drying to form a resist pattern. The resist thus formed was evaluated in the following manner.
(1)感度(L/S):
シリコンウエハー上に形成したレジスト被膜に露光して、直ちにPEBを行い、その後アルカリ現像し、水洗し、乾燥して、レジストパターンを形成した。このとき、線幅150nmのライン・アンド・スペースパターン(1L1S)を1対1の線幅に形成する露光量を最適露光量とし、この最適露光量により感度を評価した。(1) Sensitivity (L / S):
The resist film formed on the silicon wafer was exposed to light, immediately subjected to PEB, then developed with alkali, washed with water, and dried to form a resist pattern. At this time, the exposure amount for forming a line-and-space pattern (1L1S) having a line width of 150 nm in a one-to-one line width was set as the optimum exposure amount, and the sensitivity was evaluated based on the optimum exposure amount.
(2)解像度(L/S):
ライン・アンド・スペースパターン(1L1S)について、最適露光量により解像されるラインパターンの最小線幅(nm)を解像度とした。(2) Resolution (L / S):
For the line-and-space pattern (1L1S), the minimum line width (nm) of the line pattern resolved with the optimum exposure dose was taken as the resolution.
(3)膜面荒れ:
設計寸法150nmのライン・アンド・スペースパターン(1L1S)について、走査型電子顕微鏡によりラインパターンの断面寸法を測定し、最小寸法をLin、最大寸法をLoutとし、(Lout−Lin)をLdとして、Ldの値により、下記基準で評価した。
Ldが0.01μm未満:良好
Ldが0.01μm以上:不良(3) Surface roughness:
For a line-and-space pattern (1L1S) having a design dimension of 150 nm, the cross-sectional dimension of the line pattern is measured by a scanning electron microscope, the minimum dimension is Lin, the maximum dimension is Lout, and (Lout−Lin) is Ld. The following criteria were evaluated according to the value of:
Ld is less than 0.01 μm: good Ld is 0.01 μm or more: poor
本実施例の各評価結果は、感度が25.0μC/cm2であり、解像度が90nmであり、膜面荒れは良好であった。In each evaluation result of this example, the sensitivity was 25.0 μC / cm 2 , the resolution was 90 nm, and the film surface roughness was good.
(実施例5〜11、比較例1)
表1に示す各成分を表1に示した量で混合して均一溶液として、表2に示す条件で処理した以外は実施例4と同様にして組成物溶液(感放射線性組成物)を調製した。その後、調整した感放射線性組成物によってレジストパターンを形成し、形成したレジストについて上記各評価を行った。その評価結果を表2に示す。(Examples 5 to 11, Comparative Example 1)
A composition solution (radiation-sensitive composition) was prepared in the same manner as in Example 4 except that the components shown in Table 1 were mixed in the amounts shown in Table 1 to form a uniform solution and treated under the conditions shown in Table 2. did. Thereafter, a resist pattern was formed using the prepared radiation-sensitive composition, and each of the above evaluations was performed on the formed resist. The evaluation results are shown in Table 2.
なお、実施例4〜11及び比較例1に用いた材料を以下に示す。 In addition, the material used for Examples 4-11 and the comparative example 1 is shown below.
(b)感放射線性酸発生剤:
B−1:トリフェニルスルホニウムトリフルオロメタンスルホネート
B−2:N−(トリフルオロメチルスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド(B) Radiation sensitive acid generator:
B-1: Triphenylsulfonium trifluoromethanesulfonate B-2: N- (trifluoromethylsulfonyloxy) bicyclo [2.2.1] hept-5-ene-2,3-dicarboximide
(c)酸拡散制御剤:
C−1:トリ−n−オクチルアミン
C−2:トリフェニルスルホニウムサリチレート
C−3:N−t−ブトキシカルボニルジシクロヘキシルアミン(C) Acid diffusion control agent:
C-1: Tri-n-octylamine C-2: Triphenylsulfonium salicylate C-3: Nt-butoxycarbonyldicyclohexylamine
溶剤:
D−1:乳酸エチル
D−2:プロピレングリコールモノメチルエーテルアセテートsolvent:
D-1: Ethyl lactate D-2: Propylene glycol monomethyl ether acetate
表2から明らかなように、実施例1〜3の化合物のいずれかを含有する実施例4〜11の感放射線性組成物は、比較合成例1の樹脂を含有する比較例1の感放射線性組成物に比べて、電子線または極紫外線に有効に感応し、ラフネス、エッチング耐性、感度に優れ、微細パターンを高精度にかつ安定して形成することが可能な化学増幅型ポジ型レジスト膜を成膜できることが確認できた。 As is clear from Table 2, the radiation sensitive compositions of Examples 4 to 11 containing any of the compounds of Examples 1 to 3 were the radiation sensitive of Comparative Example 1 containing the resin of Comparative Synthesis Example 1. A chemically amplified positive resist film that is more sensitive to electron beams or extreme ultraviolet light than compositions, has excellent roughness, etching resistance, and sensitivity, and can form fine patterns with high accuracy and stability. It was confirmed that the film could be formed.
本発明の感放射線性組成物は、パターン形成時におけるライン・アンド・スペースパターンの解像度に優れるだけでなく、かつ、ラフネスに優れるので、EB、EUV、X線による微細パターン形成に有用である。従って、本発明の感放射線性組成物は、今後更に微細化が進行すると予想される半導体デバイス製造用の化学増幅型レジストを形成可能なものとして極めて有用である。 The radiation-sensitive composition of the present invention is not only excellent in the resolution of the line and space pattern at the time of pattern formation, but also excellent in roughness, and thus is useful for fine pattern formation by EB, EUV, and X-rays. Therefore, the radiation-sensitive composition of the present invention is extremely useful as a material capable of forming a chemically amplified resist for manufacturing semiconductor devices, which is expected to be further miniaturized in the future.
Claims (5)
(b)放射線が照射されることにより酸を発生する感放射線性酸発生剤とを含有する感放射線性組成物。
(B) A radiation-sensitive composition containing a radiation-sensitive acid generator that generates an acid when irradiated with radiation.
オニウム塩、ジアゾメタン化合物、およびスルホンイミド化合物よりなる群から選択される少なくとも一種である請求項2に記載の感放射線性組成物。 The radiation sensitive acid generator (b) is
The radiation-sensitive composition according to claim 2 , which is at least one selected from the group consisting of an onium salt, a diazomethane compound, and a sulfonimide compound.
(一般式(3−1)において、R 1 は、非置換の炭素数1〜40の、直鎖状、分岐状または環状のアルキル基であり、mは0〜3の整数である。) Following general formula (2) represented Ru of compounds.
(In General Formula (3-1), R 1 is an unsubstituted, linear, branched or cyclic alkyl group having 1 to 40 carbon atoms, and m is an integer of 0 to 3.)
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