TWI749094B

TWI749094B - 處理液及圖案形成方法

處理液及圖案形成方法 Download PDF

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Publication number: TWI749094B
Authority: TW; Taiwan
Prior art keywords: group; treatment liquid; aforementioned; film; mass
Prior art date: 2016-11-07

Application number

TW106137910A

Other languages

English (en)

Chinese (zh)

Other versions

TW201821605A (zh

Inventor

上村哲也

白川三千紘

大松禎

Original Assignee

日商富士軟片股份有限公司

Priority date

2016-11-07

Filing date

2017-11-02

Publication date

2021-12-11

2017-11-02 Application filed by 日商富士軟片股份有限公司 filed Critical 日商富士軟片股份有限公司

2018-06-16 Publication of TW201821605A publication Critical patent/TW201821605A/zh

2021-12-11 Application granted granted Critical

2021-12-11 Publication of TWI749094B publication Critical patent/TWI749094B/zh

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239000007788 liquid Substances 0.000 title claims abstract description 279
238000011282 treatment Methods 0.000 title claims abstract description 245
238000000034 method Methods 0.000 title claims abstract description 236
230000008569 process Effects 0.000 claims abstract description 118
239000002904 solvent Substances 0.000 claims abstract description 118
239000000203 mixture Substances 0.000 claims abstract description 105
230000005855 radiation Effects 0.000 claims abstract description 103
239000003960 organic solvent Substances 0.000 claims abstract description 99
238000009835 boiling Methods 0.000 claims abstract description 64
238000011161 development Methods 0.000 claims abstract description 56
230000001235 sensitizing effect Effects 0.000 claims abstract description 40
-1 alkylene carbonate Chemical compound 0.000 claims description 199
239000011347 resin Substances 0.000 claims description 125
229920005989 resin Polymers 0.000 claims description 125
239000012535 impurity Substances 0.000 claims description 115
150000001875 compounds Chemical class 0.000 claims description 65
238000001914 filtration Methods 0.000 claims description 54
239000002253 acid Substances 0.000 claims description 49
238000012545 processing Methods 0.000 claims description 37
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 28
239000003759 ester based solvent Substances 0.000 claims description 28
CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 claims description 28
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
238000010438 heat treatment Methods 0.000 claims description 26
239000012528 membrane Substances 0.000 claims description 24
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 23
MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 claims description 23
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 22
229910052804 chromium Inorganic materials 0.000 claims description 20
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 19
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 19
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 19
238000004821 distillation Methods 0.000 claims description 18
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 16
229910052742 iron Inorganic materials 0.000 claims description 16
239000005453 ketone based solvent Substances 0.000 claims description 16
229910052759 nickel Inorganic materials 0.000 claims description 16
230000009471 action Effects 0.000 claims description 15
238000005406 washing Methods 0.000 claims description 14
FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 claims description 12
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 12
229910052745 lead Inorganic materials 0.000 claims description 12
JSLCOZYBKYHZNL-UHFFFAOYSA-N butylisobutyrate Chemical compound CCCCOC(=O)C(C)C JSLCOZYBKYHZNL-UHFFFAOYSA-N 0.000 claims description 11
XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 claims description 10
AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 claims description 10
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150000002576 ketones Chemical class 0.000 claims description 9
RGFNRWTWDWVHDD-UHFFFAOYSA-N sec-butyl ester of butyric acid Natural products CCCC(=O)OCC(C)C RGFNRWTWDWVHDD-UHFFFAOYSA-N 0.000 claims description 7
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 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
150000001408 amides Chemical class 0.000 claims description 5
BGYICJVBGZQOCY-UHFFFAOYSA-N heptyl propanoate Chemical compound CCCCCCCOC(=O)CC BGYICJVBGZQOCY-UHFFFAOYSA-N 0.000 claims description 5
GOKKOFHHJFGZHW-UHFFFAOYSA-N hexyl propanoate Chemical compound CCCCCCOC(=O)CC GOKKOFHHJFGZHW-UHFFFAOYSA-N 0.000 claims description 5
TWSRVQVEYJNFKQ-UHFFFAOYSA-N pentyl propanoate Chemical compound CCCCCOC(=O)CC TWSRVQVEYJNFKQ-UHFFFAOYSA-N 0.000 claims description 5
GQKZRWSUJHVIPE-UHFFFAOYSA-N sec-amyl acetate Natural products CCCC(C)OC(C)=O GQKZRWSUJHVIPE-UHFFFAOYSA-N 0.000 claims description 5
XHIUFYZDQBSEMF-UHFFFAOYSA-N 2-methylbutyl acetate Chemical compound CCC(C)COC(C)=O XHIUFYZDQBSEMF-UHFFFAOYSA-N 0.000 claims description 4
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RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 4
VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 claims 1
230000007547 defect Effects 0.000 abstract description 55
125000000217 alkyl group Chemical group 0.000 description 121
239000000126 substance Substances 0.000 description 72
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 70
229910052799 carbon Inorganic materials 0.000 description 67
125000003118 aryl group Chemical group 0.000 description 63
229910052751 metal Inorganic materials 0.000 description 60
239000000243 solution Substances 0.000 description 58
238000000746 purification Methods 0.000 description 57
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125000000753 cycloalkyl group Chemical group 0.000 description 56
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125000001424 substituent group Chemical group 0.000 description 44
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239000000758 substrate Substances 0.000 description 39
239000011148 porous material Substances 0.000 description 38
239000004094 surface-active agent Substances 0.000 description 36
235000012431 wafers Nutrition 0.000 description 36
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 35
125000005843 halogen group Chemical group 0.000 description 28
239000000463 material Substances 0.000 description 28
239000002245 particle Substances 0.000 description 28
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238000000576 coating method Methods 0.000 description 25
230000000694 effects Effects 0.000 description 25
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125000002947 alkylene group Chemical group 0.000 description 23
238000011156 evaluation Methods 0.000 description 23
238000004519 manufacturing process Methods 0.000 description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 23
229910052710 silicon Inorganic materials 0.000 description 23
150000007514 bases Chemical class 0.000 description 22
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 22
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LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 22
229910052757 nitrogen Inorganic materials 0.000 description 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
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ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 20
239000011651 chromium Substances 0.000 description 20
230000007246 mechanism Effects 0.000 description 20
239000007769 metal material Substances 0.000 description 20
125000004093 cyano group Chemical group *C#N 0.000 description 19
239000004210 ether based solvent Substances 0.000 description 19
238000007654 immersion Methods 0.000 description 19
239000004065 semiconductor Substances 0.000 description 18
208000005156 Dehydration Diseases 0.000 description 17
230000018044 dehydration Effects 0.000 description 17
238000006297 dehydration reaction Methods 0.000 description 17
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 17
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150000001450 anions Chemical class 0.000 description 16
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125000005647 linker group Chemical group 0.000 description 15
239000007787 solid Substances 0.000 description 15
239000004215 Carbon black (E152) Substances 0.000 description 14
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ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
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239000004677 Nylon Substances 0.000 description 11
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238000006243 chemical reaction Methods 0.000 description 11
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239000003999 initiator Substances 0.000 description 9
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238000004090 dissolution Methods 0.000 description 8
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125000003277 amino group Chemical group 0.000 description 7
150000008378 aryl ethers Chemical class 0.000 description 7
BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 7
230000008859 change Effects 0.000 description 7
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
230000006866 deterioration Effects 0.000 description 7
239000011737 fluorine Substances 0.000 description 7
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
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229910052717 sulfur Inorganic materials 0.000 description 7
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 6
QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 6
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230000003078 antioxidant effect Effects 0.000 description 6
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230000000052 comparative effect Effects 0.000 description 6
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BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 6
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125000003396 thiol group Chemical group [H]S* 0.000 description 6
RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
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VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 5
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 5
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 5
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
150000005215 alkyl ethers Chemical class 0.000 description 5
229910052782 aluminium Inorganic materials 0.000 description 5
239000003945 anionic surfactant Substances 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
239000004020 conductor Substances 0.000 description 5
229910052802 copper Inorganic materials 0.000 description 5
239000010949 copper Substances 0.000 description 5
DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 5
238000010828 elution Methods 0.000 description 5
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