JP5928347B2 - パターン形成方法 - Google Patents
パターン形成方法 Download PDFInfo
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- JP5928347B2 JP5928347B2 JP2012555828A JP2012555828A JP5928347B2 JP 5928347 B2 JP5928347 B2 JP 5928347B2 JP 2012555828 A JP2012555828 A JP 2012555828A JP 2012555828 A JP2012555828 A JP 2012555828A JP 5928347 B2 JP5928347 B2 JP 5928347B2
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- 238000000034 method Methods 0.000 title claims description 63
- 230000007261 regionalization Effects 0.000 title claims description 8
- 229920000642 polymer Polymers 0.000 claims description 90
- -1 norbornanediyl group Chemical group 0.000 claims description 71
- 239000000203 mixture Substances 0.000 claims description 69
- 229920002120 photoresistant polymer Polymers 0.000 claims description 65
- 229910052731 fluorine Inorganic materials 0.000 claims description 60
- 239000002253 acid Substances 0.000 claims description 50
- 125000001153 fluoro group Chemical group F* 0.000 claims description 50
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 33
- 239000003960 organic solvent Substances 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
- 239000000758 substrate Substances 0.000 claims description 18
- 125000002723 alicyclic group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000003367 polycyclic group Chemical group 0.000 claims description 10
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 229920005601 base polymer Polymers 0.000 claims description 6
- 125000005647 linker group Chemical group 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 5
- 239000000178 monomer Substances 0.000 description 33
- 239000002904 solvent Substances 0.000 description 31
- 239000000243 solution Substances 0.000 description 24
- 238000007654 immersion Methods 0.000 description 20
- 238000006116 polymerization reaction Methods 0.000 description 20
- 238000011161 development Methods 0.000 description 18
- 230000018109 developmental process Effects 0.000 description 18
- 229920002313 fluoropolymer Polymers 0.000 description 18
- 239000004811 fluoropolymer Substances 0.000 description 18
- 239000007788 liquid Substances 0.000 description 17
- 239000011737 fluorine Substances 0.000 description 16
- 150000002430 hydrocarbons Chemical group 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 14
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 14
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 11
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 230000035945 sensitivity Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 238000001459 lithography Methods 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 7
- 239000005456 alcohol based solvent Substances 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- YFSUTJLHUFNCNZ-UHFFFAOYSA-N perfluorooctane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YFSUTJLHUFNCNZ-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000003709 fluoroalkyl group Chemical group 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- CETWDUZRCINIHU-UHFFFAOYSA-N 2-heptanol Chemical compound CCCCCC(C)O CETWDUZRCINIHU-UHFFFAOYSA-N 0.000 description 5
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 5
- 230000001771 impaired effect Effects 0.000 description 5
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- RZKSECIXORKHQS-UHFFFAOYSA-N Heptan-3-ol Chemical compound CCCCC(O)CC RZKSECIXORKHQS-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 4
- 239000003759 ester based solvent Substances 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000001226 reprecipitation Methods 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- VNBVGNOFNYFYIO-UHFFFAOYSA-N 3-fluoroprop-2-enoic acid Chemical class OC(=O)C=CF VNBVGNOFNYFYIO-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 3
- DNFSNYQTQMVTOK-UHFFFAOYSA-N bis(4-tert-butylphenyl)iodanium Chemical compound C1=CC(C(C)(C)C)=CC=C1[I+]C1=CC=C(C(C)(C)C)C=C1 DNFSNYQTQMVTOK-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 150000005676 cyclic carbonates Chemical group 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 3
- 239000004210 ether based solvent Substances 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- GJRQTCIYDGXPES-UHFFFAOYSA-N isobutyl acetate Chemical compound CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 150000002596 lactones Chemical group 0.000 description 3
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000002360 preparation method Methods 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
- 239000005871 repellent Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 150000008053 sultones Chemical group 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- UFADEYDBOXASBQ-UHFFFAOYSA-M (4-cyclohexylphenyl)-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.C1CCCCC1C1=CC=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 UFADEYDBOXASBQ-UHFFFAOYSA-M 0.000 description 2
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- GRCVHLCFMAVQCF-UHFFFAOYSA-M 2-(1-adamantyl)-1,1-difluoroethanesulfonate;triphenylsulfanium Chemical compound C1C(C2)CC3CC2CC1(CC(F)(F)S(=O)(=O)[O-])C3.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 GRCVHLCFMAVQCF-UHFFFAOYSA-M 0.000 description 2
- QNVRIHYSUZMSGM-LURJTMIESA-N 2-Hexanol Natural products CCCC[C@H](C)O QNVRIHYSUZMSGM-LURJTMIESA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- KKLIEUWPBXKNFS-UHFFFAOYSA-M 2-carboxyphenolate;triphenylsulfanium Chemical compound OC1=CC=CC=C1C([O-])=O.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 KKLIEUWPBXKNFS-UHFFFAOYSA-M 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- TYCFGHUTYSLISP-UHFFFAOYSA-N 2-fluoroprop-2-enoic acid Chemical class OC(=O)C(F)=C TYCFGHUTYSLISP-UHFFFAOYSA-N 0.000 description 2
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 2
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Natural products CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-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
- QZBAYURFHCTXOJ-UHFFFAOYSA-N 4,4,4-trifluorobut-2-enoic acid Chemical group OC(=O)C=CC(F)(F)F QZBAYURFHCTXOJ-UHFFFAOYSA-N 0.000 description 2
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- SZZCAIFFTWMNTK-UHFFFAOYSA-N C1CC[SH+]C1.[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F Chemical compound C1CC[SH+]C1.[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SZZCAIFFTWMNTK-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
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- KOFQUBYAUWJFIT-UHFFFAOYSA-M triphenylsulfanium;hydroxide Chemical compound [OH-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 KOFQUBYAUWJFIT-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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- 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
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
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- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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Description
有機溶媒現像用フォトレジスト組成物であって、
[A]酸解離性基を有する構造単位(a1)を含むベース重合体(以下、「[A]重合体」ともいう)、
[B]酸解離性基を有する構造単位(b1)を含み、フッ素原子含有率が[A]重合体より高い重合体(以下、「[B]含フッ素重合体」ともいう)、及び
[C]酸発生体
を含有し、
上記構造単位(b1)が下記式(1)又は式(2)で表されるフォトレジスト組成物である。
式(2)中、R2は、水素原子、フッ素原子、メチル基又はトリフルオロメチル基である。R3は、炭素数5〜20の脂環式炭化水素基である。)
式(4)中、R6は、水素原子、フッ素原子、メチル基又はトリフルオロメチル基である。R7は、炭素数2〜5のアルキル基である。Z2は、炭素数5又は6の2価の単環式炭化水素基又は炭素数7〜15の2価の多環式炭化水素基である。)
本発明のフォトレジスト組成物は、有機溶媒現像用フォトレジスト組成物であって、[A]重合体、[B]含フッ素重合体及び[C]酸発生体を含有する。なお、本発明の効果を損なわない限り、さらにその他の任意成分を含有してもよい。以下、各成分について詳述する。
[A]重合体は、酸解離性基を有する構造単位(a1)を含むベース重合体である。ここで、「ベース重合体」とは、フォトレジスト組成物から形成されるレジストパターンを構成する重合体の主成分となる重合体をいい、好ましくは、レジストパターンを構成する全重合体に対して50質量%以上を占める重合体をいう。また、「酸解離性基」とは、カルボキシル基等の極性官能基中の水素原子を置換する基であって、露光により[C]酸発生体から発生した酸の作用により解離する基を意味する。
構造単位(a1)は、上記式(3)又は(4)で表される構造単位であることが好ましい。
R4としては、水素原子及びメチル基が好ましい。
nとしては、1が好ましい。
R6としては、水素原子及びメチル基が好ましい。
[A]重合体は、ラクトン構造、スルトン構造又は環状カーボネート構造を有する構造単位(a2)を含んでいてもよい。[A]重合体が、構造単位(a2)を有することで、当該フォトレジスト組成物からなるレジスト膜の基板等に対する密着性が向上する。
[A]重合体は、構造単位(a1)及び後述する構造単位(b1)以外に、本願の効果を阻害しない範囲で、その他の酸解離性基を有する構造単位を含むことができる。
[A]重合体は、ラジカル重合等の常法に従って合成できる。例えば、
単量体及びラジカル開始剤を含有する溶液を、反応溶媒又は単量体を含有する溶液に滴下して重合反応させる方法;
単量体を含有する溶液と、ラジカル開始剤を含有する溶液とを各別に、反応溶媒又は単量体を含有する溶液に滴下して重合反応させる方法;
各々の単量体を含有する複数種の溶液と、ラジカル開始剤を含有する溶液とを各別に、反応溶媒又は単量体を含有する溶液に滴下して重合反応させる方法等の方法で合成することが好ましい。
n−ペンタン、n−ヘキサン、n−ヘプタン、n−オクタン、n−ノナン、n−デカン等のアルカン類;
シクロヘキサン、シクロヘプタン、シクロオクタン、デカリン、ノルボルナン等のシクロアルカン類;
ベンゼン、トルエン、キシレン、エチルベンゼン、クメン等の芳香族炭化水素類;
クロロブタン類、ブロモヘキサン類、ジクロロエタン類、ヘキサメチレンジブロミド、クロロベンゼン等のハロゲン化炭化水素類;
酢酸エチル、酢酸n−ブチル、酢酸i−ブチル、プロピオン酸メチル等の飽和カルボン酸エステル類;
アセトン、2−ブタノン、4−メチル−2−ペンタノン、2−ヘプタノン等のケトン類;
テトラヒドロフラン、ジメトキシエタン類、ジエトキシエタン類等のエーテル類;
メタノール、エタノール、1−プロパノール、2−プロパノール、4−メチル−2−ペンタノール等のアルコール類等が挙げられる。これらの溶媒は、単独で使用してもよく2種以上を併用してもよい。
当該フォトレジスト組成物は、上記式(1)又は(2)で表される酸解離性基を有する構造単位(b1)を含み、フッ素原子含有率が[A]重合体より高い[B]含フッ素重合体を含有する。当該フォトレジスト組成物が[B]含フッ素重合体を含有することで、レジスト膜を形成した際に、膜中の[B]含フッ素重合体の撥水性的特徴により、その分布がレジスト膜表面近傍で偏在化する傾向がある。その結果、当該フォトレジスト組成物は、液浸露光時に酸発生剤や酸拡散制御剤等が液浸媒体に溶出することを抑制できる。また、この[B]含フッ素重合体の撥水性的特徴により、レジスト膜と液浸媒体との前進接触角が所望の範囲に制御でき、バブル欠陥の発生を抑制できる。さらに、レジスト膜と液浸媒体との後退接触角が高くなり、水滴が残らずに高速スキャン露光が可能となる。このように当該フォトレジスト組成物は、[B]含フッ素重合体を含有することにより、液浸露光法に好適なレジスト塗膜を形成することができる。さらに、このような[B]含フッ素重合体が、酸により比較的解離し難い上記特定構造の酸解離性基を有する構造単位(b1)を含むことで、当該フォトレジスト組成物は、有機溶媒を含有する現像液に対する溶解性が適度に制御され、現像後のミッシングコンタクトホール及び露光部表面のラフネスの発生を抑制することができる。また、解像性、円形性等のリソグラフィー特性にも優れる。
構造単位(b1)は上記式(1)又は式(2)で表される。
本発明における[B]含フッ素重合体は、フッ素原子含有率が[A]重合体より高い重合体であり、フッ素原子を構造中に含む単量体を1種類以上重合することにより形成される。
[B]含フッ素重合体は、例えば所定の各構造単位に対応する単量体を、ラジカル重合開始剤を使用し、適当な溶媒中で重合することにより合成できる。
上記重合に使用されるラジカル重合開始剤及び溶媒としては、例えば[A]重合体の合成方法で挙げたものと同様のものが挙げられる。
当該フォトレジスト組成物は[C]酸発生体を含有する。[C]酸発生体は、パターン形成工程における露光により酸を発生することができる。その酸により[A]重合体及び[B]含フッ素重合体中に存在する酸解離性基を解離させ、その結果、露光部が有機溶媒を含有する現像液に難溶性となる。なお、当該フォトレジスト組成物における[C]酸発生体の含有形態は、遊離の化合物の形態(以下、「[C]酸発生剤」ともいう)でも、重合体の一部として組み込まれた形態でも、これらの両方の形態でもよい。
当該フォトレジスト組成物は、[D]含窒素化合物をさらに含んでいることが好ましい。[D]含窒素化合物は、露光により[C]酸発生体から生じる酸のレジスト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効果を奏し、レジストとしての解像度がより向上するとともに、得られるフォトレジスト組成物の貯蔵安定性が向上する。[D]含窒素化合物の当該フォトレジスト組成物における含有形態としては、遊離の化合物の形態でも、重合体の一部として組み込まれた形態でも、これらの両方の形態でもよい。
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、シクロヘキシルジメチルアミン、ジシクロヘキシルメチルアミン、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;
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、2,6−ジメチルアニリン、2,6−ジイソプロピルアニリン等の芳香族アミン類;
トリエタノールアミン、N,N−ジ(ヒドロキシエチル)アニリン等のアルカノールアミン類;
N,N,N’,N’−テトラメチルエチレンジアミン、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、1,3−ビス[1−(4−アミノフェニル)−1−メチルエチル]ベンゼンテトラメチレンジアミン、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)エーテル等が挙げられる。これらのうち、アルカノールアミン類が好ましく、トリエタノールアミンがより好ましい。
また、Anb−は、OH−、R22−COO−、R22−SO3 −(但し、R22は、それぞれ独立して、アルキル基、アリール基、又はアルカノール基である。)、又は下記式(7)で表されるアニオンである。
当該フォトレジスト組成物は、通常、[E]溶媒を含有する。[E]溶媒としては、例えばアルコール系溶媒、ケトン系溶媒、アミド系溶媒、エーテル系溶媒、エステル系溶媒及びその混合溶媒等が挙げられる。
メタノール、エタノール、n−プロパノール、iso−プロパノール、n−ブタノール、iso−ブタノール、sec−ブタノール、tert−ブタノール、n−ペンタノール、iso−ペンタノール、2−メチルブタノール、sec−ペンタノール、tert−ペンタノール、3−メトキシブタノール、n−ヘキサノール、2−メチルペンタノール、sec−ヘキサノール、2−エチルブタノール、sec−ヘプタノール、3−ヘプタノール、n−オクタノール、2−エチルヘキサノール、sec−オクタノール、n−ノニルアルコール、2,6−ジメチル−4−ヘプタノール、n−デカノール、sec−ウンデシルアルコール、トリメチルノニルアルコール、sec−テトラデシルアルコール、sec−ヘプタデシルアルコール、フルフリルアルコール、フェノール、シクロヘキサノール、メチルシクロヘキサノール、3,3,5−トリメチルシクロヘキサノール、ベンジルアルコール、ジアセトンアルコール等のモノアルコール系溶媒;
エチレングリコール、1,2−プロピレングリコール、1,3−ブチレングリコール、2,4−ペンタンジオール、2−メチル−2,4−ペンタンジオール、2,5−ヘキサンジオール、2,4−ヘプタンジオール、2−エチル−1,3−ヘキサンジオール、ジエチレングリコール、ジプロピレングリコール、トリエチレングリコール、トリプロピレングリコール等の多価アルコール系溶媒;
エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノプロピルエーテル、エチレングリコールモノブチルエーテル、エチレングリコールモノヘキシルエーテル、エチレングリコールモノフェニルエーテル、エチレングリコールモノ−2−エチルブチルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノプロピルエーテル、ジエチレングリコールモノブチルエーテル、ジエチレングリコールモノヘキシルエーテル、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プロピルエーテル、プロピレングリコールモノブチルエーテル、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、ジプロピレングリコールモノプロピルエーテル等の多価アルコール部分エーテル系溶媒等が挙げられる。
n−ペンタン、iso−ペンタン、n−ヘキサン、iso−ヘキサン、n−ヘプタン、iso−ヘプタン、2,2,4−トリメチルペンタン、n−オクタン、iso−オクタン、シクロヘキサン、メチルシクロヘキサン等の脂肪族炭化水素系溶媒;
ベンゼン、トルエン、キシレン、メシチレン、エチルベンゼン、トリメチルベンゼン、メチルエチルベンゼン、n−プロピルベンゼン、iso−プロピルベンゼン、ジエチルベンゼン、iso−ブチルベンゼン、トリエチルベンゼン、ジ−iso−プロピルベンセン、アニソール、n−アミルナフタレン等の芳香族炭化水素系溶媒;
ジクロロメタン、クロロホルム、フロン、クロロベンゼン、ジクロロベンゼン等の含ハロゲン溶媒等が挙げられる。
当該フォトレジスト組成物は、本発明の効果を損なわない範囲で、偏在化促進剤、脂環式骨格化合物、界面活性剤、増感剤等を含有できる。以下、これらのその他の任意成分について詳述する。これらのその他の任意成分は、単独で又は2種以上を混合して使用することができる。また、その他の任意成分の配合量は、その目的に応じて適宜決定することができる。
当該フォトレジスト組成物は、液浸露光法を使用しレジストパターンを形成する場合等に、偏在化促進剤を配合することができる。偏在化促進剤を配合することで、[D]重合体をさらに表層近傍に偏在化させることができる。偏在化促進剤としては、例えばγ−ブチロラクトン、プロピレンカーボネート等が挙げられる。
脂環式骨格化合物は、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さらに改善する作用を示す成分である。
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。
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[A]化合物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あり、当該フォトレジスト組成物の「みかけの感度」を向上させる効果を有する。
当該フォトレジスト組成物は、例えば上記[E]溶媒中で、上記[A]重合体、[B]含フッ素重合体、[C]酸発生体、必要に応じて加えられる[D]含窒素化合物及びその他の任意成分を所定の割合で混合することにより調製できる。当該フォトレジスト組成物は、通常、その使用に際して、全固形分濃度が1質量%〜50質量%、好ましくは2質量%〜25質量%となるように[E]溶媒に溶解した後、例えば孔径0.2μm程度のフィルターでろ過することによって調製される。
本発明のフォトレジスト組成物は、有機溶媒現像液を用いるパターン形成方法に好適に用いられる。当該フォトレジスト組成物が好適に用いられるパターン形成方法としては、例えば、(1)フォトレジスト組成物を用いて基板上にレジスト膜を形成する工程、(2)上記レジスト膜に露光する工程、及び(3)上記露光されたレジスト膜を、有機溶媒含有率が80質量%以上の現像液で現像する工程を有するパターン形成方法等が挙げられる。以下、各工程を詳述する。なお、上記パターン形成方法の(2)露光する工程における露光方法は、特に限定されるものではないが、当該フォトレジスト組成物は液浸露光に好適に用いられるため、以下に、液浸露光方法を用いる場合の各工程について説明する。
本工程では、当該フォトレジスト組成物を、基板上に直接又は下層膜等を介して塗布し、レジスト膜を形成する。基板としては、例えばシリコンウェハ、アルミニウムで被覆されたウェハ等の従来公知の基板を使用できる。また、例えば特公平6−12452号公報や特開昭59−93448号公報等に開示されている有機系又は無機系の反射防止膜を基板上に形成してもよい。上記下層膜等としては、特に限定されるものではなく、露光後の現像の際に用いられる現像液に対して不溶性であり、かつ従来のエッチング法でエッチング可能な材料であればよい。例えば半導体素子や液晶表示素子の製造において、下地材として一般的に使用されているものを用いることができる。
本工程では、工程(1)で形成したレジスト膜の所望の領域にドットパターンやラインパターンなどの特定パターンを有するマスク及び液浸液を介して縮小投影することにより露光を行う。例えば、所望の領域にアイソラインパターンマスクを介して縮小投影露光を行うことにより、トレンチパターンを形成できる。また、露光は所望のパターンとマスクパターンによって2回以上行ってもよい。2回以上露光を行う場合、露光は連続して行うことが好ましい。複数回露光する場合、例えば所望の領域にラインアンドスペースパターンマスクを介して第1の縮小投影露光を行い、続けて第1の露光を行った露光部に対してラインが交差するように第2の縮小投影露光を行う。第1の露光部と第2の露光部とは直交することが好ましい。直交することにより、露光部で囲まれた未露光部において円状のコンタクトホールパターンが形成しやすくなる。なお、露光の際に用いられる液浸液としては水やフッ素系不活性液体等が挙げられる。液浸液は、露光波長に対して透明であり、かつ膜上に投影される光学像の歪みを最小限に留めるよう屈折率の温度係数ができる限り小さい液体が好ましいが、特に露光光源がArFエキシマレーザー光(波長193nm)である場合、上述の観点に加えて、入手の容易さ、取り扱いのし易さといった点から水を用いるのが好ましい。
本工程は、工程(2)の露光後に有機溶媒を含有するネガ型現像液を用いて現像を行い、トレンチパターン及び/又はホールパターン等のパターンを形成する。ネガ型現像液とは低露光部及び未露光部を選択的に溶解・除去させる現像液のことである。ネガ型現像液が含有する有機溶媒は、アルコール系溶媒、エーテル系溶媒、ケトン系有機溶媒、アミド系溶媒、エステル系有機溶媒及び炭化水素系溶媒からなる群より選択される少なくとも1種であることが好ましい。これらの有機溶媒としては、上記[E]溶媒として挙げた有機溶媒と同様のものを挙げることができる。
カラム温度:40℃
溶出溶媒:テトラヒドロフラン(和光純薬工業社)
流速:1.0mL/分
試料濃度:1.0質量%
試料注入量:100μL
検出器:示差屈折計
標準物質:単分散ポリスチレン
[A]重合体及び後述する[B]含フッ素重合体の合成に用いた単量体を下記に示す。
化合物(M−1)14.1g(50モル%)及び化合物(M−8)15.9g(50モル%)を60gのメチルエチルケトンに溶解し、AIBN1.2g(5モル%)を添加して単量体溶液を調製した。30gのエチルメチルケトンを入れた500mLの三口フラスコを30分窒素パージした後、撹拌しながら80℃に加熱し、調製した単量体溶液を滴下漏斗にて3時間かけて滴下した。滴下開始を重合反応の開始時間とし、重合反応を6時間実施した。重合反応終了後、重合溶液を水冷して30℃以下に冷却した。600gのメタノール中に冷却した重合溶液を投入し、析出した白色粉末をろ別した。ろ別した白色粉末を120gのメタノールにてスラリー状で2回洗浄した後、ろ別し、50℃で17時間乾燥させて白色粉末状の重合体(A−1)を得た(25.4g、収率84.5%)。得られた重合体(A−1)のMwは6,900であり、Mw/Mnは1.4であった。また、13C−NMR分析の結果、化合物(M−1)由来の構造単位:化合物(M−8)由来の構造単位の含有比率は、47.5:52.5(モル%)であった。
表1に記載の単量体を所定量配合した以外は、合成例1と同様に操作して重合体(A−2)〜(A−10)を得た。また、得られた各重合体のMw、Mw/Mn、収率(%)及び各重合体における各単量体に由来する構造単位の含有率を合わせて表1に示す。
[合成例11]
化合物(M−5)35.8g(70モル%)及び化合物(M−9)14.2g(30モル%)を100gのメチルエチルケトンに溶解し、ジメチル−2,2’−アゾビスイソブチレート2.3gを添加して単量体溶液を調製した。50gの2−ブタノンを入れた500mLの三口フラスコを30分窒素パージした後、撹拌しながら80℃に加熱し、調製した単量体溶液を滴下漏斗にて3時間かけて滴下した。滴下開始を重合反応の開始時間とし、重合反応を6時間実施した。重合反応終了後、重合溶液を水冷して30℃以下に冷却し、825gのメタノール/2−ブタノン/ヘキサン=2/1/8混合溶液で洗浄した後、酢酸プロピレングリコールモノメチルエーテルで溶媒置換し、共重合体(B−1)の溶液を得た。(固形分換算で38.0g、収率76%)。この共重合体(B−1)は、Mwが7,000であり、Mw/Mnが1.40であった。13C−NMR分析の結果、化合物(M−5)由来の構造単位:化合物(M−9)由来の構造単位の含有比率(モル%)は、70.2:29.8(モル%)であった。
表1に記載の単量体を所定量配合した以外は、合成例11と同様に操作して重合体(B−2)〜(B−4)及び(b−1)を得た。また、得られた各重合体のMw、Mw/Mn、収率(%)及び各重合体における各単量体に由来する構造単位の含有率を合わせて表1に示す。
フォトレジスト組成物の調製に用いた[C]酸発生剤、[D]含窒素化合物及び[E]溶媒を以下に示す。
(C−1)〜(C−3):下記式で表される化合物
(D−1)〜(D−3):下記式で表される化合物
(E−1):酢酸プロピレングリコールモノメチルエーテル
(E−2):シクロヘキサノン
(E−3):γ−ブチロラクトン
重合体(A−1)100質量部、重合体(B−1)3質量部、酸発生剤(C−1)9.8質量部、含窒素化合物(D−1)1.8質量部、溶媒(E−1)2,220質量部、(E−2)950質量部及び(E−3)30質量部を混合し、得られた混合溶液を孔径0.2μmのフィルターでろ過して、フォトレジスト組成物を調製した。
表2に示す種類、量の各成分を使用した以外は実施例1と同様に操作して、フォトレジスト組成物を調製した。
膜厚105nmのARC66(BREWER SCIENCE社)の下層反射防止膜を形成したシリコンウェハを用い、実施例1〜25及び比較例1で調製した各フォトレジスト組成物を、それぞれ基板上にクリーントラックACT12(東京エレクトロン社)を用いてスピンコートにより塗布した。ホットプレート上にて80℃で60秒間プレベーク(PB)を行って膜厚0.10μmのレジスト膜を形成した。形成したレジスト膜に、ArF液浸露光装置(S610C、ニコン社、開口数1.30)を用いて、マスクパターン、液浸水を介して縮小投影露光を行った。次いで表3に示す温度で60秒間ポスト・エクスポージャー・ベーク(PEB)を行った後、酢酸ブチルにより23℃で30秒間現像し、4−メチル−2−ペンタノールで10秒間リンス処理を行った後、乾燥してネガ型のレジストパターンを形成した。また、他の現像液としてメチル−n−ペンチルケトン(MAK)及びアニソールを使用し、同様にパターンを形成した。なお、縮小投影後にウエハー上で直径0.055μmのホールサイズになるような露光量を最適露光量とし、この最適露光量を感度(mJ/cm2)とし、現像液として酢酸ブチルを用いた場合を表3に、MAKを用いた場合を表4に、アニソールを用いた場合を表5にそれぞれ示す。
縮小投影露光後のパターンが直径0.055μmになるドットパターンを用いて液浸水を介して縮小投影露光し、露光量を大きくしていった際に得られるホールの最小寸法を測定した。ホールの最小寸法が、0.040μm以下の場合「良好」と判断し、0.040μmを超える場合、「不良」と判断した。
上記パターン形成方法に記載の方法に従って形成したレジスト膜に、ArF液浸露光装置(S610C、ニコン社、開口数1.30)を用いて、表3〜5に記載の各最適露光量(感度)で全面露光し、表3〜5に示される各ベーク温度で60秒間PEBを行った後、酢酸ブチル、MAK又はアニソールにより23℃で30秒間現像し、4−メチル−2−ペンタノールで10秒間リンス処理を行い、乾燥してレジスト膜を形成した。本レジスト膜上の表面ラフネスを、原子間力顕微鏡(Digital Instrument社製 Nano Scope IIIa)にて測定領域40×40μmの条件下で測定した。ラフネスを測定しRMSにより算出した値が10nm未満の場合を「良好」と判断、10nm以上の場合を「不良」と判断した。
上記パターン形成方法に記載の方法に従って形成したレジスト膜に、ArF液浸露光装置(S610C、ニコン社、開口数1.30)を用いて、表3〜5に記載の各最適露光量(感度)で形成された0.055μmのホールパターンを、測長SEM(日立製作所社社、CG4000)を用いて観察し、画面上の9点のホールについて全てのパターン開口が見られれば「良好」と評価し、1つ以上のパターン閉口が見られれば「不良」と評価した。
上記パターン形成方法に記載の方法に従って形成したレジスト膜に、ArF液浸露光装置(S610C、ニコン社、開口数1.30)を用いて、表3〜5に記載の各最適露光量(感度)で形成された0.055μmのホールパターンを、測長SEM(日立ハイテクノロジーズ社、CG4000)を用いてパターン上部から観察した。ホール直径を任意の24ポイントで測定し、その測定ばらつきを3σで評価し、0.002μm以下である場合を「良好」と判断し、0.002μmを超える場合を「不良」と判断した。
上記パターン形成方法に記載の方法に従って形成したレジスト膜に、ArF液浸露光装置(S610C、ニコン社、開口数1.30)を用いて、表3〜5に記載の各最適露光量(感度)で形成された0.055μmのホールパターンの断面形状を観察し(日立ハイテクノロジーズ社、S−4800)、レジストパターンの中間での線幅Lbと膜の上部での線幅Laを測り、0.9≦(La/Lb)≦1.1の範囲内である場合を「良好」と評価し、範囲外である場合を「不良」と評価した。
Claims (4)
- フォトレジスト組成物を用いて基板上にレジスト膜を形成する工程、
上記レジスト膜に露光する工程、並びに
上記露光されたレジスト膜を有機溶媒含有率が80質量%以上の現像液で現像する工程を有し、
上記フォトレジスト組成物が、
[A]酸解離性基を有し、下記式(3)又は(4)で表される構造単位(a1)を含むベース重合体、
[B]酸解離性基を有する構造単位(b1)と、下記式(5)で表される構造単位(b2)とを含み、フッ素原子含有率が[A]重合体より高い重合体、及び
[C]酸発生体
を含有し、
上記構造単位(b1)が下記式(1)又は式(2)で表され、
上記[B]重合体の含有率が、[A]重合体100質量部に対して0.5質量部以上10質量部以下であるパターン形成方法。
式(4)中、R 6 は、水素原子、フッ素原子、メチル基又はトリフルオロメチル基である。R 7 は、炭素数2〜5のアルキル基である。Z 2 は、炭素数5又は6の2価の単環式炭化水素基又は炭素数7〜15の2価の多環式炭化水素基である。)
式(2)中、R2は、水素原子、フッ素原子、メチル基又はトリフルオロメチル基である。R3は、炭素数5〜20の脂環式炭化水素基である。)
- 上記構造単位(b1)が上記式(1)で表され、
上記式(1)のZ1の炭素数7〜10の2価の多環式炭化水素基が、ノルボルナンジイル基又はノルボルネンジイル基である請求項1に記載のパターン形成方法。 - 上記構造単位(b1)が上記式(2)で表される請求項1に記載のパターン形成方法。
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JP5900066B2 (ja) * | 2011-08-18 | 2016-04-06 | Jsr株式会社 | レジストパターン形成方法 |
JP5866180B2 (ja) * | 2011-11-14 | 2016-02-17 | 東京応化工業株式会社 | レジスト組成物及びレジストパターン形成方法 |
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JP5933249B2 (ja) * | 2011-12-16 | 2016-06-08 | 東京応化工業株式会社 | レジストパターン形成方法及びレジスト組成物 |
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JP6075980B2 (ja) * | 2012-06-27 | 2017-02-08 | 富士フイルム株式会社 | パターン形成方法及び該方法に使用するための感活性光線性又は感放射線性樹脂組成物 |
JP5737242B2 (ja) * | 2012-08-10 | 2015-06-17 | 信越化学工業株式会社 | 単量体、高分子化合物、レジスト組成物及びパターン形成方法 |
JP6148907B2 (ja) * | 2013-06-10 | 2017-06-14 | 東京応化工業株式会社 | 溶剤現像ネガ型レジスト組成物、レジストパターン形成方法 |
JPWO2016052313A1 (ja) * | 2014-09-29 | 2017-05-25 | 富士フイルム株式会社 | ネガ型のパターン形成方法、電子デバイスの製造方法、及び、感活性光線性又は感放射線性樹脂組成物 |
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