JP6858689B2 - 処理液及びパターン形成方法 - Google Patents
処理液及びパターン形成方法 Download PDFInfo
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- JP6858689B2 JP6858689B2 JP2017206436A JP2017206436A JP6858689B2 JP 6858689 B2 JP6858689 B2 JP 6858689B2 JP 2017206436 A JP2017206436 A JP 2017206436A JP 2017206436 A JP2017206436 A JP 2017206436A JP 6858689 B2 JP6858689 B2 JP 6858689B2
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- treatment liquid
- acetate
- solvent
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- 238000011282 treatment Methods 0.000 title claims description 293
- 239000007788 liquid Substances 0.000 title claims description 276
- 238000000034 method Methods 0.000 title claims description 157
- 230000007261 regionalization Effects 0.000 title claims description 8
- 239000002904 solvent Substances 0.000 claims description 153
- 239000003960 organic solvent Substances 0.000 claims description 145
- 239000011347 resin Substances 0.000 claims description 121
- 229920005989 resin Polymers 0.000 claims description 121
- 239000012535 impurity Substances 0.000 claims description 110
- 239000000203 mixture Substances 0.000 claims description 90
- 230000005855 radiation Effects 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 61
- 238000001914 filtration Methods 0.000 claims description 60
- 239000002253 acid Substances 0.000 claims description 49
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 claims description 35
- 238000009835 boiling Methods 0.000 claims description 34
- 150000002576 ketones Chemical class 0.000 claims description 29
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 claims description 28
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 27
- 229910052804 chromium Inorganic materials 0.000 claims description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 25
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 claims description 25
- 229910052742 iron Inorganic materials 0.000 claims description 25
- 229910052759 nickel Inorganic materials 0.000 claims description 25
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 24
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 23
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 22
- 238000010438 heat treatment Methods 0.000 claims description 22
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 claims description 22
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 21
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- 238000004519 manufacturing process Methods 0.000 claims description 20
- 230000009471 action Effects 0.000 claims description 18
- 238000004821 distillation Methods 0.000 claims description 17
- 229940117955 isoamyl acetate Drugs 0.000 claims description 16
- 150000001408 amides Chemical class 0.000 claims description 15
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 claims description 14
- NKIZSFXAIKPBCL-UHFFFAOYSA-N 2,5-dichloro-3,6-dimethylpyrazine Chemical compound CC1=NC(Cl)=C(C)N=C1Cl NKIZSFXAIKPBCL-UHFFFAOYSA-N 0.000 claims description 12
- XHIUFYZDQBSEMF-UHFFFAOYSA-N 2-methylbutyl acetate Chemical compound CCC(C)COC(C)=O XHIUFYZDQBSEMF-UHFFFAOYSA-N 0.000 claims description 12
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 12
- GQKZRWSUJHVIPE-UHFFFAOYSA-N sec-amyl acetate Natural products CCCC(C)OC(C)=O GQKZRWSUJHVIPE-UHFFFAOYSA-N 0.000 claims description 12
- 229940072049 amyl acetate Drugs 0.000 claims description 11
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 claims description 11
- BGYICJVBGZQOCY-UHFFFAOYSA-N heptyl propanoate Chemical compound CCCCCCCOC(=O)CC BGYICJVBGZQOCY-UHFFFAOYSA-N 0.000 claims description 11
- TWSRVQVEYJNFKQ-UHFFFAOYSA-N pentyl propanoate Chemical compound CCCCCOC(=O)CC TWSRVQVEYJNFKQ-UHFFFAOYSA-N 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- 239000003759 ester based solvent Substances 0.000 claims description 10
- GOKKOFHHJFGZHW-UHFFFAOYSA-N hexyl propanoate Chemical compound CCCCCCOC(=O)CC GOKKOFHHJFGZHW-UHFFFAOYSA-N 0.000 claims description 10
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 9
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 claims description 8
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 8
- 238000012545 processing Methods 0.000 claims description 8
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 7
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 6
- 229940043232 butyl acetate Drugs 0.000 claims description 4
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 claims description 2
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 claims 8
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 claims 8
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 7
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims 1
- -1 butyl butyl Chemical group 0.000 description 177
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- 125000000217 alkyl group Chemical group 0.000 description 117
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- 125000003118 aryl group Chemical group 0.000 description 61
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- 125000001153 fluoro group Chemical group F* 0.000 description 52
- 238000000746 purification Methods 0.000 description 51
- 229910052731 fluorine Inorganic materials 0.000 description 50
- 125000001424 substituent group Chemical group 0.000 description 50
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 41
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 40
- 238000001179 sorption measurement Methods 0.000 description 40
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- 239000004094 surface-active agent Substances 0.000 description 36
- 238000011161 development Methods 0.000 description 35
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 34
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- 239000000758 substrate Substances 0.000 description 30
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- 229910052757 nitrogen Inorganic materials 0.000 description 29
- 125000005843 halogen group Chemical group 0.000 description 28
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 125000003545 alkoxy group Chemical group 0.000 description 27
- 239000011651 chromium Substances 0.000 description 27
- 235000012431 wafers Nutrition 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 239000002245 particle Substances 0.000 description 25
- 230000002209 hydrophobic effect Effects 0.000 description 24
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 24
- 229910021645 metal ion Inorganic materials 0.000 description 24
- 125000002947 alkylene group Chemical group 0.000 description 23
- 150000007514 bases Chemical class 0.000 description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 22
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 22
- 238000011156 evaluation Methods 0.000 description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 description 21
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 20
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 20
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- 239000012487 rinsing solution Substances 0.000 description 17
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- 238000010894 electron beam technology Methods 0.000 description 16
- 150000002430 hydrocarbons Chemical class 0.000 description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
- 229920001155 polypropylene Polymers 0.000 description 16
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 15
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
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- DXVYLFHTJZWTRF-UHFFFAOYSA-N Ethyl isobutyl ketone Chemical compound CCC(=O)CC(C)C DXVYLFHTJZWTRF-UHFFFAOYSA-N 0.000 description 5
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