JP2011227454A - 窒素含有化合物を含むフォトレジスト - Google Patents
窒素含有化合物を含むフォトレジスト Download PDFInfo
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- JP2011227454A JP2011227454A JP2011012499A JP2011012499A JP2011227454A JP 2011227454 A JP2011227454 A JP 2011227454A JP 2011012499 A JP2011012499 A JP 2011012499A JP 2011012499 A JP2011012499 A JP 2011012499A JP 2011227454 A JP2011227454 A JP 2011227454A
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- Prior art keywords
- photoresist
- nitrogen
- groups
- photoresist composition
- photoacid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- -1 nitrogen-containing compound Chemical class 0.000 title claims abstract description 41
- 239000000203 mixture Substances 0.000 claims abstract description 48
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 26
- 229920002120 photoresistant polymer Polymers 0.000 claims description 98
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000010410 layer Substances 0.000 claims description 26
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 24
- 229920005989 resin Polymers 0.000 claims description 24
- 239000011347 resin Substances 0.000 claims description 24
- 229920000642 polymer Polymers 0.000 claims description 19
- 239000000758 substrate Substances 0.000 claims description 17
- 239000011247 coating layer Substances 0.000 claims description 14
- 230000005855 radiation Effects 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000004036 acetal group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 230000003213 activating effect Effects 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 3
- 230000000052 comparative effect Effects 0.000 description 17
- 125000003118 aryl group Chemical group 0.000 description 14
- 238000001878 scanning electron micrograph Methods 0.000 description 12
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 12
- 239000011230 binding agent Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 125000004122 cyclic group Chemical group 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 125000003342 alkenyl group Chemical group 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 8
- 238000003384 imaging method Methods 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
- 229910052710 silicon Inorganic materials 0.000 description 7
- 239000010703 silicon Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical group OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 125000005250 alkyl acrylate group Chemical group 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 125000002015 acyclic group Chemical group 0.000 description 4
- 230000003667 anti-reflective effect Effects 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229940116333 ethyl lactate Drugs 0.000 description 4
- 238000007654 immersion Methods 0.000 description 4
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- GQRTVVANIGOXRF-UHFFFAOYSA-N (2-methyl-1-adamantyl) prop-2-enoate Chemical compound C1C(C2)CC3CC1C(C)C2(OC(=O)C=C)C3 GQRTVVANIGOXRF-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229920003270 Cymel® Polymers 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- ODCCJTMPMUFERV-UHFFFAOYSA-N ditert-butyl carbonate Chemical compound CC(C)(C)OC(=O)OC(C)(C)C ODCCJTMPMUFERV-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000004377 microelectronic Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920001568 phenolic resin Polymers 0.000 description 3
- 239000005011 phenolic resin Substances 0.000 description 3
- 230000010287 polarization Effects 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- FDYDISGSYGFRJM-UHFFFAOYSA-N (2-methyl-2-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC1C(OC(=O)C(=C)C)(C)C2C3 FDYDISGSYGFRJM-UHFFFAOYSA-N 0.000 description 2
- IUFNOTXKUYSLPO-UHFFFAOYSA-N (3-cyano-4-bicyclo[2.2.1]heptanyl) 2-methylprop-2-enoate Chemical compound C1CC2CC(C#N)C1(OC(=O)C(=C)C)C2 IUFNOTXKUYSLPO-UHFFFAOYSA-N 0.000 description 2
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 2
- GAAFCTNQAOVBMF-UHFFFAOYSA-N CC(=C)C(O)=O.OC1COC(=O)C1 Chemical compound CC(=C)C(O)=O.OC1COC(=O)C1 GAAFCTNQAOVBMF-UHFFFAOYSA-N 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-O Htris Chemical compound OCC([NH3+])(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-O 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000001459 lithography Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000003518 norbornenyl group Chemical class C12(C=CC(CC1)C2)* 0.000 description 2
- JSGZKHJWRITPII-UHFFFAOYSA-N oxoniumylideneazanide Chemical compound O[N] JSGZKHJWRITPII-UHFFFAOYSA-N 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical group COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 229920001897 terpolymer Polymers 0.000 description 2
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 2
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 2
- GCIYMCNGLUNWNR-UHFFFAOYSA-N (2,4-dinitrophenyl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O GCIYMCNGLUNWNR-UHFFFAOYSA-N 0.000 description 1
- MCJPJAJHPRCILL-UHFFFAOYSA-N (2,6-dinitrophenyl)methyl 4-methylbenzenesulfonate Chemical class C1=CC(C)=CC=C1S(=O)(=O)OCC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O MCJPJAJHPRCILL-UHFFFAOYSA-N 0.000 description 1
- MCVVDMSWCQUKEV-UHFFFAOYSA-N (2-nitrophenyl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1=CC=CC=C1[N+]([O-])=O MCVVDMSWCQUKEV-UHFFFAOYSA-N 0.000 description 1
- LJHFIVQEAFAURQ-ZPUQHVIOSA-N (NE)-N-[(2E)-2-hydroxyiminoethylidene]hydroxylamine Chemical class O\N=C\C=N\O LJHFIVQEAFAURQ-ZPUQHVIOSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical group C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- JGTNAGYHADQMCM-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-M 0.000 description 1
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
- GYQQFWWMZYBCIB-UHFFFAOYSA-N 1-[diazo-(4-methylphenyl)sulfonylmethyl]sulfonyl-4-methylbenzene Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1=CC=C(C)C=C1 GYQQFWWMZYBCIB-UHFFFAOYSA-N 0.000 description 1
- FFKFRQVYUILJCW-UHFFFAOYSA-N 1-hydroxypyrrolidine-2,5-dione;methanesulfonic acid Chemical compound CS(O)(=O)=O.ON1C(=O)CCC1=O FFKFRQVYUILJCW-UHFFFAOYSA-N 0.000 description 1
- QPAWHGVDCJWYRJ-UHFFFAOYSA-N 1-hydroxypyrrolidine-2,5-dione;trifluoromethanesulfonic acid Chemical compound ON1C(=O)CCC1=O.OS(=O)(=O)C(F)(F)F QPAWHGVDCJWYRJ-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- FVNIIPIYHHEXQA-UHFFFAOYSA-N 2-(4-methoxynaphthalen-1-yl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C12=CC=CC=C2C(OC)=CC=C1C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 FVNIIPIYHHEXQA-UHFFFAOYSA-N 0.000 description 1
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- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical group FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical class CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- YXZXRYDYTRYFAF-UHFFFAOYSA-M 4-methylbenzenesulfonate;triphenylsulfanium Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 YXZXRYDYTRYFAF-UHFFFAOYSA-M 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
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- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
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- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical class C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
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- 238000010504 bond cleavage reaction Methods 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
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- 229940126214 compound 3 Drugs 0.000 description 1
- 239000000994 contrast dye Substances 0.000 description 1
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- 238000004132 cross linking Methods 0.000 description 1
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- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
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- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- ZHUXMBYIONRQQX-UHFFFAOYSA-N hydroxidodioxidocarbon(.) Chemical group [O]C(O)=O ZHUXMBYIONRQQX-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003903 lactic acid esters Chemical class 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000001020 plasma etching Methods 0.000 description 1
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- 229920005862 polyol Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- CYFLXLSBHQBMFT-UHFFFAOYSA-N sulfamoxole Chemical group O1C(C)=C(C)N=C1NS(=O)(=O)C1=CC=C(N)C=C1 CYFLXLSBHQBMFT-UHFFFAOYSA-N 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- TUODWSVQODNTSU-UHFFFAOYSA-M trifluoromethanesulfonate;tris[4-[(2-methylpropan-2-yl)oxy]phenyl]sulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(OC(C)(C)C)=CC=C1[S+](C=1C=CC(OC(C)(C)C)=CC=1)C1=CC=C(OC(C)(C)C)C=C1 TUODWSVQODNTSU-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- 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 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Abstract
【解決手段】複数のヒドロキシル部分を含む新規の窒素含有化合物、およびこの窒素含有化合物を含むフォトレジスト組成物。好ましい窒素含有化合物は複数(すなわち2以上)のヒドロキシル置換基、および1以上の光酸不安定基を含む。
【選択図】図1A
Description
機能的特性の性能を向上させるために、フォトレジスト組成物の構成を変更する様々な試みがなされてきた。とりわけ、フォトレジスト組成物において使用するための様々な塩基性化合物が報告されてきた。例えば、米国特許第6607870号および第7379548号を参照。
フォトレジストに使用するための本発明の好ましい窒素含有化合物は、1)2以上のヒドロキシル置換基、および2)1以上の光酸不安定基を含むことができる。典型的な光酸不安定基は、フォトレジストのリソグラフィックプロセス中(例えば、フォトレジスト層の露光後ベーキング中など)にフォトレジスト層中で露光発生酸の存在下で結合開裂を受ける。
理論に拘束されないが、本明細書において開示される窒素含有化合物はフォトレジスト中でクエンチャー成分として機能することができ、(ポジ型レジストの場合には)露光領域から未露光領域への光発生酸の移動(拡散)(この移動はレジスト層にパターン形成された像の解像度を悪化させる場合があった)を制限することができる。
Xは光酸不安定基、例えば、光酸不安定エステルもしくはアセタール基を含む。
1)248nmでの像形成に特に好適な化学増幅ポジ型レジストを提供できる酸不安定基を含むフェノール系樹脂。この種の特に好ましい樹脂には以下のものが挙げられる:i)ビニルフェノールおよびアクリル酸アルキルの重合単位を含むポリマーであって、重合されたアクリル酸アルキル単位が光酸の存在下でデブロッキング反応を受けうるポリマー。光酸誘起デブロッキング反応を受けうる代表的なアクリル酸アルキルには、例えば、アクリル酸t−ブチル、メタクリル酸t−ブチル、アクリル酸メチルアダマンチル、メタクリル酸メチルアダマンチル、および光酸誘起反応を受けうる他の非環式アルキルおよび脂環式アクリラートが挙げられ、例えば、米国特許第6,042,997号および第5,492,793号(参照により本明細書に組み込まれる)におけるポリマーが挙げられる;ii)ヒドロキシまたはカルボキシ環置換基を含まない、場合によって置換されたビニルフェニル(例えば、スチレン)、ビニルフェノール、および上記ポリマーi)について記載されるデブロッキング基のようなアクリル酸アルキルの重合単位を含むポリマー、例えば、米国特許第6,042,997号(参照により本明細書に組み込まれる)に記載されるポリマー;並びに、iii)光酸と反応できるアセタールまたはケタール部分を含む繰り返し単位を含み、および場合によってフェニルまたはフェノール性基のような芳香族繰り返し単位を含むポリマー;
2)フェニル基を実質的にまたは完全に含まず、サブ200nmの波長、例えば、193nmでの像形成に特に好適な化学増幅ポジ型レジストを提供できる樹脂。特に好ましいこの種の樹脂には次のものが挙げられる:i)非芳香族環式オレフィン(環内二重結合)、例えば、場合によって置換されたノルボルネンの重合単位を含むポリマー、例えば、米国特許第5,843,624号(参照により本明細書に組み込まれる)に記載されたポリマー;ii)アクリル酸アルキル単位、例えば、アクリル酸t−ブチル、メタクリル酸t−ブチル、アクリル酸メチルアダマンチル、メタクリル酸メチルアダマンチル、および他の非環式アルキルおよび脂環式アクリラートを含むポリマー;このようなポリマーは米国特許第6,057,083号に記載されている。この種のポリマーは、好ましい形態においては、ヒドロキシナフチルのような特定の芳香族基を含むことができる。
以下の非限定的な実施例は本発明の例示である。
2−アミノ−2−メチル−プロパン−1,3−ジオール(5部)およびドデカナール(8.5部)が90/10塩化メチレン(20部)および(15部)にそれぞれ溶解された。ドデカナール溶液が2−アミノ−2−メチル−プロパン−1,3−ジオール溶液に室温で攪拌しつつ添加された。この混合物が室温で一晩攪拌され、精製することなく次の工程で使用された。
上記混合物を氷浴中で冷却した。水素化ホウ素ナトリウム(3.8部)を50/50塩化メチレン/メタノール(20部)に溶解し、上記混合物にゆっくりと添加した。得られた混合物を室温で3時間攪拌した。化合物3を通常の水系ワークアップで単離し、次いで溶媒を除去した。
9.3部の化合物(3)および9.7部のジ−tert−ブチルカルボナートを40部の酢酸エチルに溶解し、これを6.8部のトリエタノール窒素含有で処理した。この混合物を室温で4時間攪拌した。酢酸エチルを移動相として使用するシリカゲルクロマトグラフィーで化合物4が単離された。
5部の2−アミノ−2−ヒドロキシメチル−プロパン−1,3−ジオールを70部の1:1メタノール/tert−ブタノール混合溶媒に溶解する。6.4部のジ−tert−ブチルカルボナートを50部の溶融tert−ブタノールに溶解する。ジ−tert−ブチルカルボナート/tert−ブタノール溶液を、2−アミノ−2−ヒドロキシメチル−プロパン−1,3−ジオール/1:1メタノール/tert−ブタノール溶液にゆっくりと室温で添加し、攪拌しつつ一晩維持する。溶媒を除去する。酢酸エチルから再結晶させる。
レジスト組成物の全重量を基準にした重量パーセントで表された量で以下の成分を混合することにより本発明のフォトレジストが製造される。
配合されたレジスト組成物はHMDS蒸気処理された4インチシリコンウェハ上にスピンコートされ、真空ホットプレートで90℃で60秒間ソフトベークされる。レジスト塗膜層はフォトマスクを通して193nmで露光され、次いで、露光された塗膜層が110℃で露光後ベークされる。コーティングされたウェハは次いで、0.26Nテトラメチルアンモニウムヒドロキシド水溶液で処理され、像形成されたレジスト層を現像する。
レジスト組成物の全重量を基準にした重量パーセントで表された量で以下の成分を混合することにより本発明のフォトレジストが製造される。
配合されたレジスト組成物はHMDS蒸気処理された4インチシリコンウェハ上にスピンコートされ、真空ホットプレートで90℃で60秒間ソフトベークされる。レジスト塗膜層はフォトマスクを通して193nmで露光され、次いで、露光された塗膜層が110℃で露光後ベークされる。コーティングされたウェハは次いで、0.26Nテトラメチルアンモニウムヒドロキシド水溶液で処理され、像形成されたレジスト層を現像する。
300mmシリコンウェハ上にコーティングされた有機ボトム反射防止層上に、実施例3の配合物に対応するフォトレジスト(フォトレジスト1)がスピンコートされた。このフォトレジスト1の層はソフトベークされて乾燥層厚を提供した。次いで、このフォトレジスト上に有機トップコートが適用された。フォトレジスト1の層は、次いで、193nm ASML 1900i;1.3NA CQUAD 40°0.98/0/78σXY偏光)でパターン形成するように(patternwise)液浸露光された。露光に続いて、像形成されたフォトレジスト1の層は0.26Nテトラメチルアンモニウムヒドロキシド水性現像剤で現像された。得られた現像されたフォトレジスト1の走査型電子顕微鏡写真(SEM)が図1Aに示される。
300mmシリコンウェハ上にコーティングされた有機ボトム反射防止層上に、実施例4の配合物に対応するフォトレジスト(フォトレジスト2)がスピンコートされた。このフォトレジスト2の層はソフトベークされて乾燥層厚を提供した。次いで、このフォトレジスト上に有機トップコートが適用された。フォトレジスト2の層は、次いで、193nm ASML 1900i;1.3NA CQUAD 40°0.98/0/78σXY偏光)でパターン形成するように液浸露光された。露光に続いて、像形成されたフォトレジスト2の層は0.26Nテトラメチルアンモニウムヒドロキシド水性現像剤で現像された。得られた現像されたフォトレジスト2の走査型電子顕微鏡写真(SEM)が図2Aに示される。
Claims (9)
- (a)1種以上の樹脂;
(b)1種以上の光酸発生剤化合物;並びに
(c)1種以上の窒素含有化合物であって、それぞれが1)2以上のヒドロキシル置換基、および2)1以上の光酸不安定基を含む窒素含有化合物;
を含むフォトレジスト組成物。 - 1以上の光酸不安定基が光酸不安定エステル基および/または光酸不安定アセタール基である、請求項1に記載のフォトレジスト組成物。
- 1種以上の窒素含有化合物がポリマーからなる、請求項1または2に記載のフォトレジスト組成物。
- 1種以上の窒素含有化合物が非ポリマーである、請求項1または2に記載のフォトレジスト組成物。
- 1種以上の窒素含有化合物が2000未満の分子量を有する、請求項1〜4のいずれか1項に記載のフォトレジスト組成物。
- (a)請求項1〜7のいずれか1項に記載のフォトレジスト組成物の塗膜層を基体に適用し;
(b)前記フォトレジスト塗膜層をパターン化された活性化放射線に露光し、そして露光されたフォトレジスト層を現像してレリーフ像を提供する;
ことを含む、フォトレジストレリーフ像を形成する方法。
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US8927190B2 (en) | 2015-01-06 |
US20150353482A1 (en) | 2015-12-10 |
KR20110087238A (ko) | 2011-08-02 |
CN102207678A (zh) | 2011-10-05 |
CN102207678B (zh) | 2015-05-20 |
CN104698749B (zh) | 2019-11-19 |
JP2015172057A (ja) | 2015-10-01 |
EP2348360B1 (en) | 2017-09-27 |
CN104698749A (zh) | 2015-06-10 |
TWI507462B (zh) | 2015-11-11 |
EP2348360A1 (en) | 2011-07-27 |
KR101831685B1 (ko) | 2018-02-23 |
US20110223535A1 (en) | 2011-09-15 |
US9475763B2 (en) | 2016-10-25 |
TW201137011A (en) | 2011-11-01 |
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