TWI327751B - Photoresist stripping agent - Google Patents
Photoresist stripping agent Download PDFInfo
- Publication number
- TWI327751B TWI327751B TW093100399A TW93100399A TWI327751B TW I327751 B TWI327751 B TW I327751B TW 093100399 A TW093100399 A TW 093100399A TW 93100399 A TW93100399 A TW 93100399A TW I327751 B TWI327751 B TW I327751B
- Authority
- TW
- Taiwan
- Prior art keywords
- photoresist
- formaldehyde
- release agent
- alkanolamine
- group
- Prior art date
Links
- 229920002120 photoresistant polymer Polymers 0.000 title claims description 100
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 61
- 239000007795 chemical reaction product Substances 0.000 claims description 52
- 239000003795 chemical substances by application Substances 0.000 claims description 43
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 23
- -1 aromatic thiol compound Chemical class 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 229940102253 isopropanolamine Drugs 0.000 claims description 10
- ANYPUYLKMDXVRK-UHFFFAOYSA-N 2-aminoethanol;formaldehyde Chemical compound O=C.NCCO ANYPUYLKMDXVRK-UHFFFAOYSA-N 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 238000012360 testing method Methods 0.000 claims description 7
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims description 6
- 150000003973 alkyl amines Chemical class 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 claims description 5
- 238000000227 grinding Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 claims description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 claims description 3
- LJDSTRZHPWMDPG-UHFFFAOYSA-N 2-(butylamino)ethanol Chemical compound CCCCNCCO LJDSTRZHPWMDPG-UHFFFAOYSA-N 0.000 claims description 3
- BCLSJHWBDUYDTR-UHFFFAOYSA-N 2-(propylamino)ethanol Chemical compound CCCNCCO BCLSJHWBDUYDTR-UHFFFAOYSA-N 0.000 claims description 3
- 239000002738 chelating agent Substances 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 229920000768 polyamine Polymers 0.000 claims description 3
- 150000005846 sugar alcohols Chemical class 0.000 claims description 3
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 2
- PXWASTUQOKUFKY-UHFFFAOYSA-N 2-(methylamino)propan-1-ol Chemical compound CNC(C)CO PXWASTUQOKUFKY-UHFFFAOYSA-N 0.000 claims description 2
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 claims description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
- 239000012298 atmosphere Substances 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- SGBGCXQCQVUHNE-UHFFFAOYSA-N 2-(ethylamino)propan-1-ol Chemical compound CCNC(C)CO SGBGCXQCQVUHNE-UHFFFAOYSA-N 0.000 claims 1
- 239000003759 ester based solvent Substances 0.000 claims 1
- 150000002443 hydroxylamines Chemical class 0.000 claims 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
- 239000000758 substrate Substances 0.000 description 15
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000004065 semiconductor Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 7
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 239000001569 carbon dioxide Substances 0.000 description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 description 6
- 238000005530 etching Methods 0.000 description 6
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 5
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 4
- 229930040373 Paraformaldehyde Natural products 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229910021417 amorphous silicon Inorganic materials 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910052732 germanium Inorganic materials 0.000 description 3
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 3
- VIDOWPWTFHJVID-UHFFFAOYSA-N 2,3,5-trimethyl-1h-pyrrole Chemical compound CC1=CC(C)=C(C)N1 VIDOWPWTFHJVID-UHFFFAOYSA-N 0.000 description 2
- UIAFKZKHHVMJGS-UHFFFAOYSA-N 2,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- BKMMTJMQCTUHRP-UHFFFAOYSA-N 2-aminopropan-1-ol Chemical compound CC(N)CO BKMMTJMQCTUHRP-UHFFFAOYSA-N 0.000 description 2
- YQUVCSBJEUQKSH-UHFFFAOYSA-N 3,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 description 2
- UYEMGAFJOZZIFP-UHFFFAOYSA-N 3,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC(O)=C1 UYEMGAFJOZZIFP-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 241000208340 Araliaceae Species 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 2
- QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 2
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- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 2
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 2
- 235000003140 Panax quinquefolius Nutrition 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 2
- 235000005487 catechin Nutrition 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 229950001002 cianidanol Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 2
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 229940074391 gallic acid Drugs 0.000 description 2
- 235000004515 gallic acid Nutrition 0.000 description 2
- 235000008434 ginseng Nutrition 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XHFGWHUWQXTGAT-UHFFFAOYSA-N n-methylpropan-2-amine Chemical compound CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 2
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
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- 241000894007 species Species 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
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- 235000012431 wafers Nutrition 0.000 description 2
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 2
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- SQGSVBHTFQOZDL-UHFFFAOYSA-N (2-Methylpropyl)(propyl)amine Chemical compound CCCNCC(C)C SQGSVBHTFQOZDL-UHFFFAOYSA-N 0.000 description 1
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- CUVLMZNMSPJDON-UHFFFAOYSA-N 1-(1-butoxypropan-2-yloxy)propan-2-ol Chemical compound CCCCOCC(C)OCC(C)O CUVLMZNMSPJDON-UHFFFAOYSA-N 0.000 description 1
- QWOZZTWBWQMEPD-UHFFFAOYSA-N 1-(2-ethoxypropoxy)propan-2-ol Chemical compound CCOC(C)COCC(C)O QWOZZTWBWQMEPD-UHFFFAOYSA-N 0.000 description 1
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- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- SERLAGPUMNYUCK-DCUALPFSSA-N 1-O-alpha-D-glucopyranosyl-D-mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O SERLAGPUMNYUCK-DCUALPFSSA-N 0.000 description 1
- HRMRQBJUFWFQLX-UHFFFAOYSA-N 1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-3-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1CCC(C(O)=O)C1 HRMRQBJUFWFQLX-UHFFFAOYSA-N 0.000 description 1
- LXQMHOKEXZETKB-UHFFFAOYSA-N 1-amino-2-methylpropan-2-ol Chemical compound CC(C)(O)CN LXQMHOKEXZETKB-UHFFFAOYSA-N 0.000 description 1
- KODLUXHSIZOKTG-UHFFFAOYSA-N 1-aminobutan-2-ol Chemical compound CCC(O)CN KODLUXHSIZOKTG-UHFFFAOYSA-N 0.000 description 1
- JPZYXGPCHFZBHO-UHFFFAOYSA-N 1-aminopentadecane Chemical compound CCCCCCCCCCCCCCCN JPZYXGPCHFZBHO-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-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
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 1
- AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical compound C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 description 1
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- AXKVOSSFZLZIDC-UHFFFAOYSA-N n,n-diaminoaniline Chemical compound NN(N)C1=CC=CC=C1 AXKVOSSFZLZIDC-UHFFFAOYSA-N 0.000 description 1
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- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 1
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- KFYKZKISJBGVMR-UHFFFAOYSA-N n-ethylbutan-2-amine Chemical compound CCNC(C)CC KFYKZKISJBGVMR-UHFFFAOYSA-N 0.000 description 1
- KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 description 1
- VDUIPQNXOQMTBF-UHFFFAOYSA-N n-ethylhydroxylamine Chemical compound CCNO VDUIPQNXOQMTBF-UHFFFAOYSA-N 0.000 description 1
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- NJWMENBYMFZACG-UHFFFAOYSA-N n-heptylheptan-1-amine Chemical compound CCCCCCCNCCCCCCC NJWMENBYMFZACG-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- CPQCSJYYDADLCZ-UHFFFAOYSA-N n-methylhydroxylamine Chemical compound CNO CPQCSJYYDADLCZ-UHFFFAOYSA-N 0.000 description 1
- UOIWOHLIGKIYFE-UHFFFAOYSA-N n-methylpentan-1-amine Chemical compound CCCCCNC UOIWOHLIGKIYFE-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- CATWEXRJGNBIJD-UHFFFAOYSA-N n-tert-butyl-2-methylpropan-2-amine Chemical compound CC(C)(C)NC(C)(C)C CATWEXRJGNBIJD-UHFFFAOYSA-N 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
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- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- LPGZAWSMGCIBOF-UHFFFAOYSA-N pentane-1,2-diamine Chemical compound CCCC(N)CN LPGZAWSMGCIBOF-UHFFFAOYSA-N 0.000 description 1
- WTSXICLFTPPDTL-UHFFFAOYSA-N pentane-1,3-diamine Chemical compound CCC(N)CCN WTSXICLFTPPDTL-UHFFFAOYSA-N 0.000 description 1
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- 229940100684 pentylamine Drugs 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- PZZICILSCNDOKK-UHFFFAOYSA-N propane-1,2,3-triamine Chemical compound NCC(N)CN PZZICILSCNDOKK-UHFFFAOYSA-N 0.000 description 1
- GGOZGYRTNQBSSA-UHFFFAOYSA-N pyridine-2,3-diol Chemical compound OC1=CC=CN=C1O GGOZGYRTNQBSSA-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 150000003304 ruthenium compounds Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical compound C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- ZERJNAGZUCPHNB-UHFFFAOYSA-N tetrazane Chemical compound NNNN ZERJNAGZUCPHNB-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- MAKDTFFYCIMFQP-UHFFFAOYSA-N titanium tungsten Chemical compound [Ti].[W] MAKDTFFYCIMFQP-UHFFFAOYSA-N 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- QFKMMXYLAPZKIB-UHFFFAOYSA-N undecan-1-amine Chemical compound CCCCCCCCCCCN QFKMMXYLAPZKIB-UHFFFAOYSA-N 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
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- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- E—FIXED CONSTRUCTIONS
- E03—WATER SUPPLY; SEWERAGE
- E03D—WATER-CLOSETS OR URINALS WITH FLUSHING DEVICES; FLUSHING VALVES THEREFOR
- E03D9/00—Sanitary or other accessories for lavatories ; Devices for cleaning or disinfecting the toilet room or the toilet bowl; Devices for eliminating smells
- E03D9/08—Devices in the bowl producing upwardly-directed sprays; Modifications of the bowl for use with such devices ; Bidets; Combinations of bowls with urinals or bidets; Hot-air or other devices mounted in or on the bowl, urinal or bidet for cleaning or disinfecting
-
- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/42—Stripping or agents therefor
- G03F7/422—Stripping or agents therefor using liquids only
- G03F7/425—Stripping or agents therefor using liquids only containing mineral alkaline compounds; containing organic basic compounds, e.g. quaternary ammonium compounds; containing heterocyclic basic compounds containing nitrogen
-
- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/42—Stripping or agents therefor
- G03F7/422—Stripping or agents therefor using liquids only
- G03F7/426—Stripping or agents therefor using liquids only containing organic halogen compounds; containing organic sulfonic acids or salts thereof; containing sulfoxides
Description
1327751 玖、發明說明: (一) 發明所屬之技術領域 光阻已用於以微影製造範圍廣泛之裝 路(如LC與LSI )、顯示裝置(如LCD |5 刷電路板、微機械、DNA晶片、及顯微移 地關於用於自各種負載光阻之基板去除光 劑。 (二) 先前技術 在習知技術中,光阻係藉鹼剝離劑去 鹼剝離劑之光阻剝離力對半導體裝置與液 中近來發展之精密程序及短期處理不足。 一步改良剝離力。已提議含羥基胺之光阻 ,羥基胺易於分解。爲了解決以上之問題 甲基胺結構之化合物之光阻體剝離劑(例 請案公開第2000-250230號)。然而,仍 阻剝離力之需求。 各種材料已用於近來半導體積體電路 之半導體製造。因此,需要發展一種不腐 種基板之光阻體剝離劑。 此外,已知光阻體剝離劑之光阻剝離 因爲吸收空氣中之二氧化碳氣體而降低。 (三) 發明內容 本發明之目的爲解決以上已知光阻體 及提供一種在低溫於短時間內可易於去除 置,包括積體電 ! EL裝置)、印 除。本發明特別 阻之光阻體剝離 除。然而,已知 晶顯示面板製造 因此,已要求進 體剝離劑。然而 ,已提議含具羥 如,曰本專利申 有進一步改良光 與液晶顯示裝置 蝕這些材料與各 力在長期使用時 剝離劑之問題, 塗佈於基板上之 -5 - 1327751 光阻層、在蝕刻後殘留之光阻層、及蝕刻除灰後之光阻殘 渣之光阻體剝離劑。本發明之另一個目的爲提供一種可去 除光阻層與光阻殘渣而不腐蝕基板、絕緣層、線路材料等 ,因而造成精密處理及製造高精確電路之光阻體剝離劑。 本發明之另一個目的爲提供一種使用此光阻體剝離組成物 去除光阻之方法。本發明之另一個目的爲提供一種其光阻 剝離力因吸收空氣中之二氧氧化碳降低極小之光阻體剝離 劑。 廣泛硏究之結果,發明人已發現一種光阻體剝離劑, 其含由莫耳比例(甲醛/烷醇胺)爲0.8或更小之甲醛與烷 醇胺之反應製造之反應產物。此光阻體剝離劑在低溫於短 時間內易於去除塗佈於基板上之光阻層、在蝕刻後殘留之 光阻層、及蝕刻除灰後之光阻殘渣。此光阻體剝離劑亦去 除光阻層及光阻殘渣而不腐蝕基板線路材料、絕緣層等, 而造成精密處理及提供高精確電路。 (四)實施方式 本發明之光阻體剝離劑含至少一種甲醛-烷醇胺反應產 物’其爲甲醛與烷醇胺間反應之產物。至於胺與醛之反應 產物之實例,在此技藝已知羥甲基胺。本發明之光阻體剝 離齊I含一種羥甲基胺以外之甲醛-烷醇胺反應產物作爲有效 成分。此甲醛-烷醇胺反應產物之化學結構尙未完全得知。 例如’以下之化學結構敘述於Chemical Review,第126卷 0939)第297-338頁,美國專利第5,4 86,605號,日本專利 公告第46-26903號,及蘇聯專利第1 534029號: 1327751
其中R1與R3爲衍生自胺之取代基,r2爲衍生自醛之取代 基。 此甲醛-烷醇胺反應產物係藉甲醛與烷醇胺之反應製造 °可使用福馬林與多聚甲醛作爲甲醛。烷醇胺之實例包括 乙醇胺、N·甲基乙醇胺、N-乙基乙醇胺、N-丙基乙醇胺、N-丁基乙醇胺、二乙醇胺、異丙醇胺、N-甲基異丙醇胺、N-乙基異丙醇胺、N-丙基異丙醇胺、2-胺基丙-1-醇、N-甲基-2-胺基丙-1·醇、與N-乙基-2·胺基丙-1-醇,以乙醇胺、N_ 甲基乙醇胺、與異丙醇胺特佳。 爲了製造此甲醛-烷醇胺反應產物.,烷醇胺可單獨或以 二或更多種之組合使用。此外,此甲醛-烷醇胺反應產物可 以無機酸或有機酸之鹽之形式使用。 此甲醛-烷醇胺反應產物之較佳實例包括甲醛-單乙醇 胺縮合物與甲醛-異丙醇胺縮合物。 此甲醛-烷醇胺反應產物之光阻剝離力因鹼化合物之共 存而增強。鹼化合物之實例包括烷胺、烷醇胺、多胺、環 形胺、四級銨化合物、與羥基胺化合物。 烷胺之實例包括一級烷胺,如甲胺、乙胺、正丙胺、 異丙胺、正丁胺、二級丁胺、異丁胺、三級丁胺、戊胺、2-胺基戊胺、3-胺基戊胺、1-胺基-2-甲基丁胺、2-胺基-2-甲 -7- 1327751 基丁胺' 3-胺基-2-甲基丁胺' 4-胺基-2-甲基丁胺、己胺、 · 5-胺基-2-甲基戊胺、庚胺、辛胺、壬胺、癸胺、十一碳胺 . 、十二碳胺、十三碳胺、十四碳胺、十五碳胺、十六碳胺 、十七碳胺、與十八碳胺;二級烷胺,如二甲胺、二乙胺 、二丙胺、二異丙胺、二丁胺、二異丁胺、二-二級丁胺、 二-三級丁胺、二戊胺、二己胺、二庚胺、二辛胺、二壬胺 、二癸胺、甲乙胺、甲丙胺、甲基異丙基胺、甲丁胺、甲 基異丁基胺、甲基二級丁基胺、甲基三級丁基胺、甲戊胺 、甲基異戊基胺、乙丙胺、乙基異丙基胺、乙丁胺、乙基 Φ 異丁基胺、乙基二級丁基胺、乙胺、乙基異戊基胺、丙丁 胺、與丙基異丁基胺;三級烷胺,如三甲胺、三乙胺、三 丙胺、三丁胺、三戊胺、二甲基乙基胺、甲基二乙基胺、 - 與甲基二丙基胺。 - 烷醇胺之實例包括乙醇胺、N-甲基乙醇胺、N-乙基乙 醇胺、N-丙基乙醇胺、N-丁基乙醇胺 '二乙醇胺、異丙醇 胺、N-甲基異丙醇胺、N-乙基異丙醇胺、N-丙基異丙醇胺 、2-胺基丙-1-醇、N-甲基-2-胺基丙-1-醇、N-乙基-2-胺基 β 丙-1-醇、1-胺基丙-3-醇、Ν-甲基-卜胺基丙-3-醇、Ν-乙基-1-胺基丙-3-醇、1-胺基丁 -2-醇、Ν-甲基-卜胺基丁 -2-醇、Ν-乙基-1-胺基丁 -2-醇、2-胺基丁 -1-醇、Ν-甲基-2-胺基丁 -1-醇、Ν-乙基-2-胺基丁 -1-醇、3-胺基丁 -1-醇、Ν-甲基-3-胺 基丁 -1-醇、Ν-乙基-3-胺基丁 -1-醇、1-胺基丁 -4-醇、Ν-甲 基-1-胺基丁 -4-醇、Ν-乙基-1-胺基丁 -4-醇、1-胺基-2-甲基 丙-2-醇、2-胺基-2-甲基丙-1-醇、1-胺基戊-4-醇、2-胺基-4- -8- 1327751 甲基戊-1-醇、2-胺基己-1-醇、3-胺基庚_4·醇、胺基辛-2-醇、5-胺基辛-4-醇、卜胺基丙-2,3-二醇、2-胺基丙-1,3-二 醇、参(氧甲基)胺基甲烷、1,2-二胺基丙-3-醇、1,3-二胺 基丙-2-醇、與2-(2-胺基乙氧基)乙醇。 多胺之實例包括乙二胺' 丙二胺、伸丙二胺、伸丁二 胺、1,3-二胺基丁烷、2,3-二胺基丁烷、伸戊二胺、2,4-二 胺基戊烷、伸己二胺、伸庚二胺、伸辛二胺、伸壬二胺、N-甲基乙二胺、N,N-二甲基乙二胺、三甲基乙二胺' N_乙基 乙二胺、N,N-二乙基乙二胺、三乙基乙二胺、1,2,3-三胺基 丙烷、肼、参(2 -胺基乙基)胺、四(胺基甲基)甲烷、 二伸乙三胺、三伸乙四胺、四乙基五胺、七伸乙八胺、九 伸乙十胺、與二氮雙環十一碳烯。 羥基胺化合物之實例包括羥基胺、N-甲基羥基胺、N-乙基羥基胺、N,N-二乙基羥基胺 '與〇-甲基羥基胺。 環形胺之實例包括吡咯、2-甲基吡咯、3-甲基吡咯、2-乙基吡咯、3-乙基吡咯、2,3-二甲基吡咯、2,4-二甲基吡咯 、3,4-二甲基吡咯、2,3,4-三甲基吡咯、2,3,5-三甲基吡咯 、2 -吡咯啉、3 -吡咯啉、吡咯啶、2 -甲基吡咯啶、3 -甲基吡 咯啶 '吡唑、咪唑、1,2,3-三唑' 1,2,3,4-四唑、哌啶、2-哌可啉、3 -哌可啉、4 -哌可啉、2,4 -二甲基哌啶、2,6-二甲 基哌啶、3,5 -二甲基哌啶、哌嗪、2 -甲基哌嗪、2,5 -二甲基 哌嗪、2,6·二甲基哌嗪、與嗎啉。 四級銨化合物之實例包括氫氧化四甲銨、氫氧化四乙 -9- 1327751 銨、氫氧化四丙銨、氫氧化四丁銨、膽鹼氫氧化物、與乙 醯膽鹼氫氧化物。 甲醛-烷醇胺反應產物本質亦可作爲鹼化合物,因爲其 爲鹼性化合物。 除了上列之鹼化合物,其他化合物可用於本發明而無 任何限制,只要其顯示鹼性本性。 以上之鹼化合物中,較佳爲甲胺、乙胺 '丙胺、丁胺 、乙醇胺、N-甲基乙醇胺、N-乙基乙醇胺、二乙醇胺、異 丙醇胺、2-(2 -胺基乙氧基)乙醇、乙二胺、丙二胺、丁 二胺、二伸乙三胺、六氫吡哄、與嗎啉。 鹼化合物可單獨或以二或更多種之組合使用。 爲了增強光阻剝離力,本發明之光阻體剝離劑可含有 機溶劑。有機溶劑並未特別地限制,只要其與烷醇胺-甲醛 反應產物互溶。溶於水中之有機溶劑較佳。其實例包括醚 溶劑,如乙二醇、乙二醇單乙醚、乙二醇單丁醚、二乙二 醇單甲醚 '二乙二醇單乙醚、二乙二醇單丁醚、丙二醇單 甲醚 '丙二醇單乙醚、丙二醇單丁醚 '二丙二醇單甲醚、 二丙二醇單乙醚、二丙二醇單丁醚、乙二醇二甲醚、與二 丙二醇二甲醚;醯胺溶劑,如甲醯胺、單甲基甲醯胺、二 甲基甲醯胺、單乙基甲醯胺、二乙基甲醯胺、乙醯胺、單 甲基乙醯胺、二甲基乙醯胺、單乙基乙醯胺、二乙基乙醯 胺、N-甲基吡咯啶酮、與N_乙基吡咯啶酮;醇溶劑,如甲 醇、乙醇、異丙醇、乙二醇 '與丙二醇;亞碾溶劑,如二 甲基亞碾;碾溶劑,如二甲楓、二乙碾、貳(2-羥基碾)、 -10- 1327751 與伸丁楓;咪唑啶酮溶劑,如1,3-二甲基_2_咪唑啶酮' ι,3- . 二乙基-咪唑啶酮、與丨,3·二異丙基-2-咪唑啶酮:及內酯 溶劑,如γ-丁內醋與δ-戊內醋。 以上之溶劑中’較佳爲一甲基亞碾、Ν,Ν_二甲基甲醯 胺、Ν,Ν -—甲基乙酿胺、Ν -甲基卩比略陡酮、二乙二醇單甲 醚、二乙一醇單丁酸、一丙二醇單甲酸、二丙二醇單丁酸 、與丙二醇’因爲這些溶劑易得且因其高沸點而易於處理 〇 本發明之光阻體剝離劑可含抗腐触劑,如芳族經基化 0 合物 '糖醇、三唑化合物 '與螯合劑。 芳族羥基化合物之實例包括酚、甲苯酌、二甲苯、兒 茶酣 '三級丁基兒茶酣、間苯二酌 '氫醒、五倍子酸、1,2,4_ - 苯并三唑、柳醇、對羥基苄醇、鄰羥基苄醇、對經基苯乙 _ 醇、對胺基酣、間胺基酹、二胺基酣、胺基間苯二酣、對 羥基苯甲酸、鄰羥基苯甲酸、2,4 -二羥基苯甲酸、2,5-二經 基苯甲酸、3,4_二羥基苯甲酸、3,5_二羥基苯甲酸、與五倍 子酸。糖醇之實例包括葡萄糖醇 '木糖醇、與palatinit。 φ 三唑化合物之實例包括苯并三唑 '胺基三唑、與胺基四哇 。螯合劑之實例包括磷酸爲主化合物,如1,2 -丙二胺伸丁 基磷酸與羥基乙烷磷酸;羧酸爲主化合物,如乙二胺四乙 酸、二羥乙基甘胺酸、亞硝基三乙酸、草酸 '檸檬酸、丙 二酸、與酒石酸;胺化合物,如二吡啶 '四苯基卟啉 '啡 啉 '與2,3 -吡啶二醇;肟化合物,如二甲基乙二醒二肟、 與二苯基乙二醛二肟;及乙炔化合物,如苯基乙炔與2,5_ -11- 1327751 二甲基-3·己炔-2,5-二醇。這些化合物可單獨或以二或更多 , 種之組合使用》 光阻體剝離劑中甲醛-烷醇胺反應產物之含量較佳爲 0.001至100重量%,而且更佳爲0.01至50重量%。驗化 合物之含量較佳爲光阻體剝離劑之〇至99.999重量%,更 佳爲10至99.99重量%。由於甲醛-烷醇胺反應產物亦可作 爲鹼化合物,僅含甲醛-烷醇胺反應產物之光阻體剝離劑具 有足以用於光阻剝離之效果。 有機溶劑之含量可依照光阻體剝離劑之黏度與比重, φ 及蝕刻與除灰程序之條件選擇,而未特別地限制。以光阻 體剝離劑重量計,較佳爲此含量爲0至9 9重量%,而且更 佳爲1 〇至9 9重量%。 - 抗腐蝕劑之含量並未特別地限制。如果使用,則以光 - 阻體剝離劑重量計,抗腐蝕劑之含量較佳爲0.1至30重量 %,而且更佳爲1至15重量%。 在本發明中使用水並不重要,而且其含量可依照飩刻 與除灰程序之條件等決定。如果使用,則以光阻體剝離劑 ® 重量計,水之含量較佳爲1至50重量%,而且更佳爲5至 4 0重量%。 羥甲基胺通常在胺與甲醛間反應中如等莫耳反應產物 而得。然而,本發明之指定特點在於使用羥甲基胺以外之 甲醛·烷醇胺反應產物。日本專利申請案公開第200〇-25〇35〇 號教示羥甲基胺增強光阻剝離力。儘管此教示,發明人已 發現光阻剝離力可藉羥甲基胺以外之甲醛-烷醇胺反應產物 -12- 1327751 進一步增強而完成本發明。然而應注意,本發明不排除使 - 用羥甲基胺組合甲醛-烷醇胺反應產物。 對於光阻剝離特別有效爲一種甲醛與過量烷醇胺間反 應製造之甲醛-烷醇胺反應產物。甲醛/烷醇胺之莫耳比例較 佳爲0.8或更小,更佳爲0.001至0.8,而且仍更佳爲〇.〇1 至 0.5。 在本發明中,甲醛-烷醇胺反應產物係以以下方式製造 。將甲醛緩慢地加入預定量之烷醇胺中,以將甲醛/烷醇胺 莫耳比例調節至以上範圍內。甲醛加入較佳爲在攪拌下經3 0 φ 至1200分鐘完成,同時將反應溶液之溫度維持在70 °C,較 佳爲30至60°C。在完成甲醛加入後,較佳爲持續攪拌30 至1200分鐘,同時將反應溶液之溫度維持在7(TC,較佳爲 -30至60°C,因而完成反應。此反應較佳爲在惰氣大氣中進 -行,例如,在氮氣流中。此外,此反應可在無溶劑下進行 ,或可在上述有機溶劑存在下進行。最終反應溶液可作爲 光阻體剝離劑而無需分離甲醛-烷醇胺反應產物。 以上方式製造之甲醛-烷醇胺反應產物(特別是甲醛-® 乙醇胺反應產物)之化學結構特徵爲13C-NMR (DMSO-d6) 光譜中至少45至50、61至62、與64至70 ppm之峰。 甲醛-烷醇胺反應產物因以下方式而視爲具光阻剝離效 果。在使光阻體剝離劑接觸光阻時,其中之甲醛-烷醇胺反 應產物鍵結至光阻而增加光阻之溶解度,如此利於光阻去 除。Mannich反應產物視爲可助於光阻剝離。光阻之分解 與溶解因鹼化合物之共存而促成,如此增強光阻剝離力。 -13- 1327751 本發明之光阻體剝離劑在半導體裝置製造中之光阻去 _ 除通常在室溫至1 5 0 °c進行。由於本發明之光阻體剝離劑可 在低至70 °C或更低之溫度去除光阻,其可有效地防止不欲 之半導體材料之侵蝕。 本發明之光阻體剝離劑可應用於由各種材料製造之半 導體裝置製造中之光阻去除。此材料之實例包括矽、非晶 矽、多晶矽、氧化矽、氮化矽、銅、銅合金、鋁、鋁合金 '金、鉑、銀、鈦、鈦-鎢、氮化鈦、鎢、鉬、鉅化合物、 鉻、氧化鉻、鉻合金、半導體線路材料(如氧化銦錫(ιτο) φ )、複合半導體(如鎵-砷、鎵-磷、與銦-磷)、介電材料 (如緦-鉍-鉅)、及LCD基板用玻璃》 在半導體裝置製造中使用本發明之光阻體剝離劑之光 - 阻去除係藉’例如,以下之方式進行。將光阻組成物塗佈 . 於形成於基板上之導電層上而形成光阻層,然後藉曝光及 顯影將其圖樣化。使用圖樣化光阻層之作爲光罩而蝕刻導 電層之未遮蔽區域。然後使經蝕刻基板接觸光阻體剝離劑 而去除殘留之光阻層。如果需要,殘留之光阻層可在蝕刻 Φ 程序後接受除灰處理,然後使用光阻體剝離劑去除光阻殘 渣。在去除光阻層或光阻殘渣後,可將基板以有機溶劑( 如醇)或水淸洗。 本發明參考以下之實例而更詳細地解釋,其不應視爲 限制本發明之範圍。 合成例1 甲醛-單乙醇胺縮合物(醛/胺=0.5草百比)之製浩 -14- 1327751 將15克之三聚甲醛在攪拌下緩慢地加入61.0克之單 乙醇胺中,同時將溶液冷卻以將溫度維持在70。(:或更低, 因而得到溶液形式之反應產物A。所有之步驟係在氮氣流 中進行。反應產物A之13C-NMR光譜(DMSO-d6)之圖表示 於第1圖。在第1圖中’EA爲單乙醇胺,mlEA爲羥甲基 乙醇胺,及FEA爲甲醛-單乙醇胺反應產物。 合成例2 甲醛-單乙醇胺縮合物(醛/胺=0.8草耳bh)夕製浩 將24克之三聚甲醛在攪拌下緩慢地加入61.0克之單 φ 乙醇胺中,同時將溶液冷卻以將溫度維持在70 °C或更低, 因而得到溶液形式之反應產物A。所有之步驟係在氮氣流 中進行。 · 實例1 - 5及比較例1 - 2 - 將預先以矽化合物表面處理之6吋矽晶圓以光阻劑 PFR-7900旋塗。藉由在160°C烘烤,製備載有1〇,〇〇〇埃 厚光阻層之基板。 將如此製備之基板在1 5 0 °C浸於表1所列之各光阻體 鲁 剝離劑。在預定之時間間隔後,自光阻體剝離劑取出各基 板,以水淸洗,以氮氣吹風乾燥,然後在光學顯微鏡下觀 察以測定去除光阻層所需之時間。結果示於表1。 1327751 表1 烷醇胺 甲醛-烷醇胺反應產物 溶劑A 光阻去除所需時間 種類 重量% 種類 雷量% 麵 重量% 實例 1 EA 65 反應產物A 5 DMSO 30 20秒 2 EA 65 反應產物A 5 DMAC 30 20秒 3 EA 65 反應產物B 5 DMSO 30 30秒 4 EA 66.5 反應產物B 3.5 DMSO 30 40秒 5 EA 69 反應產物A 1 DMSO 30 60秒 比較例 1 EA 70 - - DMSO 30 180秒 2 EA 69 mlEA 1 DMSO 30 120秒 EA :單 D M A C · DMSO : m 1 E A : 乙醇胺 二甲基乙醯胺 二甲基亞碾 羥甲基乙醇胺 實例6 -9及比較例 3-4 使 二氧 化碳 氣 ,體流入6 8 · 5 克之單乙醇胺與 30克之 DMSO 之混合溶液中而溶解 1.5 克之二氧化碳, 所得液體 稱爲「 二氧化碳退化剝離液體」。 在將表 2所示之各添加
劑加入二氧化碳退化剝離液體後,以如實例1 - 5之相同方 式進行光阻剝離測試。結果示於表2。 1327751 表2 添加劑 光阻去除所需時間 種類 重量% 實例 6 反應產物A 5 30秒 7 反應產物A 2.5 60秒 8 反應產物A 1.25 90秒 9 反應產物A 檸檬酸 5 30秒 1 比較例 3 - - 240秒 4 檸檬酸 1 240秒 實例10
重複合成例1之製造,除了將多聚甲醛改成32%福馬 林而製備甲醛-單乙醇胺反應產物。使用如此製備之甲醛-單乙醇胺反應產物,以如實例1之相同方式進行光阻剝離 測試。光阻層在浸漬20秒後完全去除。 實例1 1 重複合成例1之製造,除了將單乙醇胺改成異丙醇胺 而製備甲醛·單乙醇胺反應產物。使用如此製備之甲醛-單 乙醇胺反應產物,以如實例1之相同方式進行光阻剝離測 試。光阻層在浸漬20秒後完全去除。 實例1 2 在30克之二甲基亞碾中,使1克之多聚甲醛與69克 之單乙醇胺(醛/胺=0.03莫耳比)反應而製造含甲醛-單 -17- 1327751 乙醇胺反應產物之溶液。使用如此得到之溶液,以如實例 .. 1之相同方式進行光阻剝離測試。光阻層在浸漬3 0秒後 . 完全去除。 實例1 3 腐鈾測試 將載有鋁層之非晶矽(a-Si)基板在70 °C浸於實例3-7 之各光阻體剝離劑,對a-Si使用光學厚度計及對A1使用 螢光X射線而測定a-Si與A1之蝕刻速率。對a-Si與A1 之蝕刻速率均爲5埃/分鐘或更小。 φ 本發明之光阻體剝離劑可在短時間內去除光阻層與光 阻殘渣而不腐蝕基板、線路材料等。此外,本發明之光阻 體剝離劑抗因吸收二氧化碳氣體造成之光阻剝離力退化。 - (五)圖式簡單說明 . 第1圖爲顯示甲醛與單乙醇胺之反應液體(醛/胺=0.5 莫耳比)之"C-NMR光譜之圖表。在49.31、61.19、64.72 、與6 8.7 5 ppm發現歸因於反應液體中甲醛-單乙醇胺反應 產物之峰化學偏移。 ♦
Claims (1)
1327751 ,.晶五f舻搬頁I 第93 1 003 99號「光阻體剝離劑」專利案 (2009年12月18日修正) - 拾、申請專利範圍: 1. —種光阻體剝離劑,其包括一種由莫耳比例爲0.8或更小 之甲醛與烷醇胺之反應所產生之反應產物,其中烷醇胺爲 至少一種選自由乙醇胺、N -甲基乙醇胺、N-乙基乙醇胺、 N-丙基乙醇胺、N-丁基乙醇胺、二乙醇胺 '異丙醇胺、N-甲基異丙醇胺、N -乙基異丙醇胺、N-丙基異丙醇胺、2-胺 基丙-1-醇、N -甲基-2-胺基丙-1-醇、與N -乙基-2-胺基丙-1-醇所組群組之化合物。 2. 如申請專利範圍第1項之光阻體剝離劑,其進一步包括驗 化合物。 - 3. 如申請專利範圍第2項之光阻體剝離劑,其中鹼化合物爲 · 至少一種選自由烷胺、烷醇胺、多胺、環形胺、四級銨鹽 、與羥基胺化合物所組群組之化合物。 4. 如申請專利範圍第1項之光阻體剝離劑,其進一步包括有 機溶劑。 ® 5. 如申請專利範圍第4項之光阻體剝離劑,其中有機溶劑爲 至少一種選自由醚溶劑、醯胺溶劑、醇溶劑、亞碾溶劑、 碾溶劑、咪嗖啶酮溶劑、與內酯溶劑所組群組之溶劑。 6. 如申請專利範圍第1項之光阻體剝離劑,其進一步包括抗 腐蝕劑。 7. 如申請專利範圍第6項之光阻體剝離劑,其中抗腐蝕劑爲 至少一種選自由芳族經基化合物、糖醇、三哩化合物、與 -1 - 1327751 年月日 I rrQQ 19.- \ 8 tj ^-SL ..-J 螯合劑所組群組之化合物。 ’ 8 ·如申請專利範圍第1項之光阻體剝離劑,其進一步包括水 · 〇 9 ·如申請專利範圍第1至8項中任一項之光阻體剝離劑,其 包括0.001至100重量%之甲醛與烷醇胺之反應產物,及 至少一種選自由〇至99.999重量%之鹼化合物、0至99重 量%之有機溶劑、0.1至30重量%之抗腐蝕劑、與1至50 重量%之水所組群組之選用成分,各百分比係由各範圍選 擇使得其總和達1 〇〇重量%。 φ 1 0 ·如申請專利範圍第1至8項中任一項之光阻體剝離劑,其 中甲醛與烷醇胺之反應產物爲甲醛-單乙醇胺縮合物或甲 醛-異丙醇胺縮合物。 ^ Π.如申請專利範圍第1至8項中任一項之光阻體剝離劑,其 · 中甲醛與烷醇胺之反應產物係藉包括以下之方法製造: 將甲醛在攪拌下經30至1 20 0分鐘緩慢地加入預定量之 烷醇胺中,同時將反應溶液之溫度維持在7〇°C或更低之步 驟;及 β 進一步將反應溶液攪拌30至120 0分鐘,同時將反應 溶液之溫度維持在7〇 °C或更低之選用步驟’ 各步驟係在鈍氣大氣中進行。 12.如申請專利範圍第1至8項中任一項之光阻體剝離劑’其 中在以13C-NMR(DMSO-d6)測量時,甲醛與烷醇胺之反應 產物至少在45至50、61至62、與64至70 ppm顯示峰。
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-
2003
- 2003-01-09 JP JP2003003700A patent/JP4085262B2/ja not_active Expired - Lifetime
-
2004
- 2004-01-05 SG SG200400024-6A patent/SG135013A1/en unknown
- 2004-01-05 US US10/750,822 patent/US20040137379A1/en not_active Abandoned
- 2004-01-08 TW TW093100399A patent/TWI327751B/zh not_active IP Right Cessation
- 2004-01-09 CN CNB2004100020764A patent/CN100472331C/zh not_active Expired - Lifetime
- 2004-01-09 KR KR1020040001351A patent/KR101085255B1/ko active IP Right Grant
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- 2006-08-02 US US11/497,251 patent/US20060270574A1/en not_active Abandoned
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CN1517803A (zh) | 2004-08-04 |
TW200416864A (en) | 2004-09-01 |
JP2004219486A (ja) | 2004-08-05 |
KR20040064234A (ko) | 2004-07-16 |
KR101085255B1 (ko) | 2011-11-22 |
US20060270574A1 (en) | 2006-11-30 |
SG135013A1 (en) | 2007-09-28 |
CN100472331C (zh) | 2009-03-25 |
US20040137379A1 (en) | 2004-07-15 |
JP4085262B2 (ja) | 2008-05-14 |
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