CN1517803A - 光致抗蚀剂脱除剂 - Google Patents
光致抗蚀剂脱除剂 Download PDFInfo
- Publication number
- CN1517803A CN1517803A CNA2004100020764A CN200410002076A CN1517803A CN 1517803 A CN1517803 A CN 1517803A CN A2004100020764 A CNA2004100020764 A CN A2004100020764A CN 200410002076 A CN200410002076 A CN 200410002076A CN 1517803 A CN1517803 A CN 1517803A
- Authority
- CN
- China
- Prior art keywords
- photoresist
- formaldehyde
- agent
- alkanolamine
- removes
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920002120 photoresistant polymer Polymers 0.000 claims abstract description 114
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 68
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 57
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 52
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- -1 isopropyl hydramine Chemical compound 0.000 claims description 32
- 229940102253 isopropanolamine Drugs 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical group NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 13
- 239000003513 alkali Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- ANYPUYLKMDXVRK-UHFFFAOYSA-N 2-aminoethanol;formaldehyde Chemical group O=C.NCCO ANYPUYLKMDXVRK-UHFFFAOYSA-N 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 10
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 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
- 239000007859 condensation product Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 238000003756 stirring Methods 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
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 claims description 4
- 150000003973 alkyl amines Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 4
- 150000003462 sulfoxides Chemical class 0.000 claims description 4
- LJDSTRZHPWMDPG-UHFFFAOYSA-N 2-(butylamino)ethanol Chemical compound CCCCNCCO LJDSTRZHPWMDPG-UHFFFAOYSA-N 0.000 claims description 3
- 239000013522 chelant Substances 0.000 claims description 3
- 229920000768 polyamine Polymers 0.000 claims description 3
- 150000005846 sugar alcohols Chemical class 0.000 claims description 3
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 239000004210 ether based solvent Substances 0.000 claims description 2
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 abstract description 12
- 238000005530 etching Methods 0.000 abstract description 10
- 239000000463 material Substances 0.000 abstract description 9
- 238000012545 processing Methods 0.000 abstract description 2
- 239000000758 substrate Substances 0.000 abstract 2
- 238000004380 ashing Methods 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 34
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 14
- 239000011159 matrix material Substances 0.000 description 12
- 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000001569 carbon dioxide Substances 0.000 description 7
- 229910002092 carbon dioxide Inorganic materials 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 229910021417 amorphous silicon Inorganic materials 0.000 description 5
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 5
- 229920002866 paraformaldehyde Polymers 0.000 description 5
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000002169 ethanolamines Chemical class 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
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-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
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000015165 citric acid Nutrition 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 3
- 238000005498 polishing Methods 0.000 description 3
- CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical compound OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 3
- CUVLMZNMSPJDON-UHFFFAOYSA-N 1-(1-butoxypropan-2-yloxy)propan-2-ol Chemical compound CCCCOCC(C)OCC(C)O CUVLMZNMSPJDON-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
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 2
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-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
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 2
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical group NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical group 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
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-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
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- PYFSCIWXNSXGNS-UHFFFAOYSA-N N-methylbutan-2-amine Chemical compound CCC(C)NC PYFSCIWXNSXGNS-UHFFFAOYSA-N 0.000 description 2
- QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- 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
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- GGNQRNBDZQJCCN-UHFFFAOYSA-N benzene-1,2,4-triol Chemical compound OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 2
- 229940113088 dimethylacetamide Drugs 0.000 description 2
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 2
- CPQCSJYYDADLCZ-UHFFFAOYSA-N n-methylhydroxylamine Chemical compound CNO CPQCSJYYDADLCZ-UHFFFAOYSA-N 0.000 description 2
- GVWISOJSERXQBM-UHFFFAOYSA-N n-methylpropan-1-amine Chemical compound CCCNC GVWISOJSERXQBM-UHFFFAOYSA-N 0.000 description 2
- XHFGWHUWQXTGAT-UHFFFAOYSA-N n-methylpropan-2-amine Chemical compound CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 2
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 2
- BVJSUAQZOZWCKN-UHFFFAOYSA-N p-hydroxybenzyl alcohol Chemical compound OCC1=CC=C(O)C=C1 BVJSUAQZOZWCKN-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- GGHDAUPFEBTORZ-UHFFFAOYSA-N propane-1,1-diamine Chemical compound CCC(N)N GGHDAUPFEBTORZ-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- 229910052715 tantalum Inorganic materials 0.000 description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 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
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 2
- KFYKZKISJBGVMR-ZCFIWIBFSA-N (2r)-n-ethylbutan-2-amine Chemical compound CCN[C@H](C)CC KFYKZKISJBGVMR-ZCFIWIBFSA-N 0.000 description 1
- JJZONEUCDUQVGR-WXUKJITCSA-N (NE)-N-[(2E)-2-hydroxyimino-1,2-diphenylethylidene]hydroxylamine Chemical compound c1ccccc1\C(=N/O)\C(=N\O)\c1ccccc1 JJZONEUCDUQVGR-WXUKJITCSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- QESSFIPIJPVTLG-UHFFFAOYSA-N 1,3-di(propan-2-yl)imidazol-2-one Chemical compound CC(C)N1C=CN(C(C)C)C1=O QESSFIPIJPVTLG-UHFFFAOYSA-N 0.000 description 1
- NLLZIERPOVNIIA-UHFFFAOYSA-N 1,3-diethylimidazol-2-one Chemical compound CCN1C=CN(CC)C1=O NLLZIERPOVNIIA-UHFFFAOYSA-N 0.000 description 1
- CFQPVBJOKYSPKG-UHFFFAOYSA-N 1,3-dimethylimidazol-2-one Chemical compound CN1C=CN(C)C1=O CFQPVBJOKYSPKG-UHFFFAOYSA-N 0.000 description 1
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 1
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-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
- 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
- MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical compound CCS(=O)(=O)CC MBDUIEKYVPVZJH-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
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- WTMJHBZSSSDBFQ-UHFFFAOYSA-N 2,3,4-trimethyl-1h-pyrrole Chemical class CC1=CNC(C)=C1C WTMJHBZSSSDBFQ-UHFFFAOYSA-N 0.000 description 1
- VIDOWPWTFHJVID-UHFFFAOYSA-N 2,3,5-trimethyl-1h-pyrrole Chemical class CC1=CC(C)=C(C)N1 VIDOWPWTFHJVID-UHFFFAOYSA-N 0.000 description 1
- PCAXITAPTVOLGL-UHFFFAOYSA-N 2,3-diaminophenol Chemical group NC1=CC=CC(O)=C1N PCAXITAPTVOLGL-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明的光致抗蚀剂脱除剂包含由摩尔比为0.8或0.8以下的甲醛与烷醇胺进行反应而得到的反应产物。该光致抗蚀剂脱除剂能在低温下,在短时间内迅速除去涂敷在各种基体上的光致抗蚀剂层、经蚀刻后留下的光致抗蚀剂层以及经蚀刻磨光后的光致抗蚀剂残留物。该光致抗蚀剂脱除剂在除去光致抗蚀剂层和光致抗蚀剂残留物时不会对基体、导线材料、绝缘层等产生腐蚀作用,因而能实施精细加工和制成高精密电路。
Description
技术领域
光致抗蚀剂已广泛应用于多种器件的平版印制过程中,其中包括集成电路(如IC和LSI),显示器(如LCD和EL器件),印制板、微机、DNA芯片以及微型设备。本发明尤其涉及从各种带有光致抗蚀剂的基体上除去光致抗蚀剂的光致抗蚀剂脱除剂。
背景技术
对于常规技术来说,光致抗蚀剂是借助碱性脱除剂除去的。然而,已知的碱性脱除剂对光致抗蚀剂的脱除效能不能满足于近来研发的用于制造半导体器件和液晶显示板的精细加工和快速处理的要求。因此,需要进一步提高脱除效能。已经提出了一种含羟胺的抗蚀剂脱除剂。然而,羟胺容易分解。为了解决上述问题,已经研制了一种含具有羟甲胺结构化合物的抗蚀剂脱除剂(例如日本专利申请公开No.2000-250230)。然而,仍需要进一步提高脱除抗蚀剂的效能。
由于制造半导体器件的半导体集成电路和液晶显示器件时采用了多种材料,因此,需要研制一种对这些材料和各种基体没有腐蚀性的光致抗蚀剂脱除剂。
此外,已知的光致抗蚀剂脱除剂在长时间使用过程中会因吸收空气中二氧化碳而降低脱除光致抗蚀剂的效能。
发明内容
本发明的一个目的是解决已知光致抗蚀剂脱除剂存在的上述问题,以及提供一种能在低温下、在较短时间内迅速除去涂敷在各种基体上的光致抗蚀剂层,经蚀刻后留下的光致抗蚀剂层以及经蚀刻磨光后的光致抗蚀剂残留物的光致抗蚀剂脱除剂。本发明的另一个目的是提供一种不会对基体、绝缘层、导线材料等产生腐蚀作用的,能除去光致抗蚀剂层和光致抗蚀剂残留物的光致抗蚀剂脱除剂,从而能实施精细加工和制造高精密电路。本发明的再一个目的是提供一种采用光致抗蚀剂脱除组合物来脱除光致抗蚀剂的方法。本发明的还有一个目的是提供一种在吸收了空气中二氧化碳后几乎不会降低其脱除光致抗蚀剂效能的光致抗蚀剂脱除剂。
由于进行了广泛的研究,本发明者已发现了含有由摩尔比(甲醛/烷醇胺)为0.8或低于0.8的甲醛与烷醇胺进行反应所得的反应产物的光致抗蚀剂脱除剂。这种光致抗蚀剂脱除剂能在低温下、在短时间内迅速除去涂敷在各种基体上的光致抗蚀剂层、经蚀刻后留下的光致抗蚀剂层以及经蚀刻磨光后的光致抗蚀剂残留物。该光致抗蚀剂脱除剂在除去光致抗蚀剂层和光致抗蚀剂残留物时不会对基体、导线材料和绝缘层产生腐蚀作用,因而能实施精细加工和提供高精密电路。
附图说明
图1是甲醛与单乙醇胺(醛/胺摩尔比=0.5)反应液体的13C-NMR谱图。甲醛-单乙醇胺在反应液体中的反应产物的化学位移峰分别出现在49.31、61.19、64.72和68.75ppm。
具体实施方式
本发明的光致抗蚀剂脱除剂包含至少一种甲醛-烷醇胺反应产物。作为胺与醛反应产物的实例,甲醇胺在技术上是已知的。本发明的光致抗蚀剂脱除剂包含除羟甲基胺外的、作为有效成分的甲醛-烷醇胺的反应产物。甲醛-烷醇胺反应产物的化学结构尚未完全清楚。例如,Chemical Review(Vol.126(1939),P297-338)、美国专利NO.5486605、日本专利公报NO.46-26903和前苏联专利NO.1534029给出了下列化学结构:
式中R1和R3为由胺衍生的取代基基团,R2为由醛衍生的取代基基团。
甲醛-烷醇胺反应产物是通过甲醛与乙醇胺反应而制得的。福尔马林与多聚甲醛都可用作原料甲醛。烷醇胺的实例包括乙醇胺、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、异丙醇胺、N-甲基异丙醇胺、N-乙基异丙醇胺、N-丙基异丙醇胺、2-氨基丙烷-1-醇、N-甲基-2-氨基-丙烷-1-醇以及N-乙基-2-氨基-丙烷-1-醇,而乙醇胺、N-甲基乙醇胺和异丙醇胺是特别优选的。
为了制备甲醛-烷醇胺反应产物,可采用单一的烷醇胺或两种或两种以上烷醇胺的混合物。此外,甲醛-烷醇胺反应产物也可以与无机酸或有机酸的盐的形态使用。
甲醛-烷醇胺反应产物的优选实例包括甲醛-单乙醇胺缩合物和甲醛-异丙醇胺缩合物。
甲醛-烷醇胺反应产物通过与碱化合物共存而提高了脱除光致抗蚀剂的效能。碱化合物的实例包括烷基胺、烷醇胺、多胺、环胺、季铵化合物和羟胺化合物。
烷基胺的实例包括烷基伯胺如甲胺、乙胺、正丙胺、异丙胺、正丁胺、仲丁胺、异丁胺、叔丁胺、戊胺、2-氨基戊烷、3-氨基戊烷、1-氨基-2-甲基丁烷、2-氨基-2-甲基丁烷、3-氨基-2-甲基丁烷、4-氨基-2-甲基丁烷、己胺、5-氨基-2-甲基戊烷、庚胺、辛胺、壬胺、癸胺、十一烷基胺、十二烷基胺、十三烷基胺、十四烷基胺、十五烷基胺、十六烷基胺、十七烷基胺和十八烷基胺,烷基仲胺如二甲胺、二乙胺、二丙胺、二异丙胺、二丁胺、二异丁胺、二仲丁胺、二叔丁胺、二戊胺、二己胺、二庚胺、二辛胺、二壬胺、二癸胺、甲乙胺、甲基丙胺、甲基异丙胺、甲基丁胺、甲基异丁胺、甲基仲丁胺、甲基叔丁胺、甲基戊胺、甲基异戊胺、乙基丙胺、乙基异丙胺、乙基丁胺、乙基异丁胺、乙基仲丁胺、乙胺、乙基异戊胺、丙基丁胺和丙基异丁胺;烷基叔胺如三甲胺、三乙胺、三丙胺、三丁胺、三戊胺、二甲基乙胺、甲基二乙胺和甲基二丙胺。
烷醇胺的实例包括乙醇胺、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、异丙醇胺、N-甲基异丙醇胺、N-乙基异丙醇胺、N-丙基异丙醇胺、2-氨基丙烷-1-醇、N-甲基-2-氨基丙烷-1-醇、N-乙基-2-氨基丙烷-1-醇、1-氨基丙烷-3-醇、N-甲基-1-氨基丙烷-3-醇、N-乙基-1-氨基丙烷-3-醇、1-氨基丁烷-2-醇、N-甲基-1-氨基丁烷-2-醇、N-乙基-1-氨基丁烷-2-醇、2-氨基丁烷-1-醇、N-甲基-2-氨基丁烷-1-醇、N-乙基-2-氨基丁烷-1-醇、3-氨基丁烷-1-醇、N-甲基-3-氨基丁烷-1-醇、N-乙基-3-氨基丁烷-1-醇、1-氨基丁烷-4-醇、N-甲基-1-氨基丁烷-4-醇、N-乙基-1-氨基丁烷-4-醇、1-氨基-2-甲基丙烷-2-醇、2-氨基-2-甲基丙烷-1-醇、1-氨基戊烷-4-醇、2-氨基-4-甲基戊烷-1-醇、2-氨基己烷-1-醇、3-氨基庚烷-4-醇、1-氨基辛烷-2-醇、5-氨基辛烷-4-醇、1-氨基丙烷-2,3-二醇、2-氨基丙烷-1,3-二醇、三(甲氧基)氨基甲烷、1,2-二氨基丙烷-3-醇、1,3-二氨基丙烷-2-醇以及2-(2-氨基乙氧基)乙醇。
多胺的实例包括乙二胺、丙二胺、三亚甲基二胺、四亚甲基二胺、1,3-二氨基丁烷、2,3-二氨基丁烷、五亚甲基二胺、2,4-二氨基戊烷、六亚甲基二胺、七亚甲基二胺、八亚甲基二胺、九亚甲基二胺、N-甲基亚乙基二胺、N,N-二甲基亚乙基二胺、三甲基亚乙基二胺、N-乙基亚乙基二胺、N,N-二乙基亚乙基二胺、三乙基亚乙基二胺、1,2,3-三氨基丙烷、肼、三(2-氨基乙基)胺、四(氨基甲基)甲烷、二亚乙基三胺、三亚乙基四胺、四乙基五胺、七亚乙基八胺、九亚乙基十胺以及二氮杂双环十一烯。
羟胺化合物的实例包括羟胺、N-甲基羟胺、N-乙基羟胺、N,N-二乙基羟胺以及O-甲基羟胺。
环胺的实例包括吡咯、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、吡咯烷、2-甲基吡咯烷、3-甲基吡咯烷、吡唑、咪唑、1,2,3-三唑、1,2,3,4-四唑、哌啶、2-甲基哌啶、3-甲基哌啶、4-甲基哌啶,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-甲基哌嗪和吗啉。
季铵化合物的实例包括氢氧化四甲铵、氢氧化四乙铵、氢氧化四丙铵、氢氧化四丁铵、氢氧化胆碱和氢氧化乙酰胆碱。
由于甲醛-烷醇胺反应产物也是碱性化合物,因而其本身也能作为碱化合物。
除上述碱化合物外,其它化合物也可用于本发明中,只要化合物呈碱性,不受任何特定的限制。
上述碱化合物中优选的是甲胺、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、异丙醇胺、2-(2-氨基乙氧基)乙醇、乙二胺、丙二胺、丁二胺、二亚乙基三胺、哌嗪和吗啉。
碱化合物可单独使用或以两种或两种以上相结合使用。
为了提高对光致抗蚀剂的脱除效能,本发明的光致抗蚀剂脱除剂可包含有机溶剂。对该有机溶剂没有特别的限制,只要能与烷醇胺-甲醛反应产物混溶。可溶于水的有机溶剂是优选的。这类有机溶剂的实例包括醚溶剂如乙二醇、乙二醇单乙醚、乙二醇单丁醚、二甘醇单甲醚、二甘醇单乙醚、二甘醇单丁醚、丙二醇单甲醚、丙二醇单乙醚、丙二醇单丁醚、一缩二丙二醇单甲醚、一缩二丙二醇单乙醚、一缩二丙二醇单丁醚、乙二醇二甲醚和一缩二丙二醇二甲醚;酰胺溶剂如甲酰胺、一甲基甲酰胺、二甲基甲酰胺、一乙基甲酰胺、二乙基甲酰胺、乙酰胺、一甲基乙酰胺、二甲基乙酰胺、一乙基乙酰胺、二乙基乙酰胺、N-甲基吡咯烷酮和N-乙基吡咯烷酮;醇溶剂如甲醇、乙醇、异丙醇、乙二醇和丙二醇;亚砜溶剂如二甲亚砜;砜溶剂如二甲砜、二乙砜、双(2-羟基砜)和四亚甲基砜;咪唑啉酮溶剂如1,3-二甲基-2-咪唑啉酮、1,3-二乙基-2-咪唑啉酮和1,3-二异丙基-2-咪唑啉酮;以及内酯溶剂如γ-丁内酯和6-戊内酯。
上述溶剂中优选的是二甲亚砜、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基吡咯烷酮、二甘醇单甲醚、二甘醇单丁醚、一缩二丙二醇单甲醚、一缩二丙二醇单丁醚和丙二醇,这些溶剂是容易购得的,并由于沸点高也是容易处理的。
本发明的光致抗蚀剂脱除剂可含防腐蚀剂如芳族羟基化合物、糖醇、三唑化合物及螯合化合物。
芳族羟基化合物的实例包括苯酚、甲酚、二甲酚、邻苯二酚、叔丁基邻苯二酚、间苯二酚、氢醌、连酚三酚、1,2,4-苯三酚、水杨醇、对羟基苄醇、邻羟基苄醇、对羟基苯乙醇、对氨基酚、间氨基酚、二氨基酚、氨基间苯二酚、对羟基苯甲酸、邻羟基苯甲酸、2,4-二羟基苯甲酸、2,5-二羟基苯甲酸、3,4-二羟基苯甲酸、3,5-二羟基苯甲酸和鞣酸。糖醇的实例包括山梨醇、木糖醇和异构麦芽糖。三唑化合物的实例包括苯并三唑、氨基三唑和氨基四唑。螯合化合物的实例包括磷酸基化合物如1,2-丙烷二胺四亚甲基膦酸和羟乙烷膦酸;羟酸基化合物如亚乙基二胺四乙酸、二羟乙基氨基乙酸、氮川三乙酸、草酸、柠檬酸、苹果酸和酒石酸;胺化合物如联吡啶、四苯基卟啉、菲咯啉和2,3-吡啶二醇;肟化合物如二甲基乙二肟和二苯基乙二肟以及乙炔化合物如苯基乙炔和2,5-二甲基-3-己炔-2,5-二醇。这些化合物可单独使用,也可以两种或两种以上结合使用。
光致抗蚀剂脱除剂中甲醛-烷醇胺反应产物的含量优选为0.001-100重量%,更优选为0.01-50重量%。碱化合物含量优选为0-99.999重量%,更优选为10-99.99重量%(以光致抗蚀剂脱除剂的重量计)。由于甲醛-烷醇胺反应产物也能起碱化合物作用,因此,只含甲醛-烷醇胺反应产物的光致抗蚀剂脱除剂也具有足够的脱除光致抗蚀剂的作用。
有机溶剂的含量可根据光致抗蚀剂脱除剂的粘度和比重以及蚀刻条件和磨光工艺进行选择,不受特定的限制。优选的含量为0-99重量%,更优选为10-99重量%(以光致抗蚀剂脱除剂重量计)。
对防腐蚀剂的用量没有特别的限制。根据需要,防腐蚀剂的用量优选为0.1-30重量%,更优选为1-15重量%(以光致抗蚀剂脱除剂重量计)。
在本发明中水的使用并不是关键,其用量可根据蚀刻条件和磨光工艺来确定。根据需要,水的用量优选为1-50重量%,更优选为5-40重量%(以光致抗蚀剂脱除剂重量计)。
一般来说,甲醇胺是以胺与甲醛间进行反应得到的等摩尔反应产物。然而,本发明特定特征在于采用不同于羟甲基胺的甲醛-烷醇胺的反应产物。日本专利申请公开No.2000-250350介绍了羟甲基胺能提高光致抗蚀剂的脱除效能。针对这项结果,本发明者发现,脱除光致抗蚀剂的效能可通过不同于羟甲基胺的甲醛-烷醇胺反应产物而得到进一步的提高,从而达到了本发明的目的。然而,应该指出,本发明中不排除羟甲基胺与甲醛-烷醇胺反应产物的结合使用。
特别有效的脱除光致抗蚀剂成分是由甲醛与过量烷醇胺进行反应制得的甲醛-烷醇胺反应产物。甲醛/烷醇胺的摩尔比优选为0.8或0.8以下,更优选为0.001-0.8,再更优选为0.01-0.5。
在本发明中,甲醛-烷醇胺反应产物是按下述方法制得的:缓慢地将甲醛添加到预定量的烷醇胺中,以使甲醛/烷醇胺的摩尔比调整到上述范围内,甲醛的添加最好在反应溶液的温度为70℃(优选为30-60℃)下借助搅拌、在30-1200分钟内完成;甲醛加毕后,最好在反应溶液的温度为70℃(优选30-60°)下再搅拌30-1200分钟,以使反应完全;该反应优选在惰性气氛例如氮气流中进行。此外,该反应可在没有溶剂的条件下,或者在上述有机溶剂中进行。最后的反应溶液无需分离甲醛-烷醇胺反应产物,就可用作光致抗蚀剂脱除剂。
按上述方法制得的甲醛-烷醇胺反应产物,特别是甲醛-乙醇胺反应产物的化学结构的特征在于:13C-NMR(DMSO-d6)谱图中至少出现45-50、61-62和64-70ppm化学位移峰。
可以认为甲醛-烷醇胺反应产物是基于下述方式呈现光致抗蚀剂脱除效能的。当光致抗蚀剂脱除剂与光致抗蚀剂接触时,其中甲醛-烷醇胺反应产物就会与光致抗蚀剂相结合,提高了光致抗蚀剂的溶解度,从而有助于脱除光致抗蚀剂。据认为,Mannich反应产物可能有助于光致抗蚀剂的脱除。由于共存有碱化合物促进了光致抗蚀剂的分解和溶解,因而提高了对光致抗蚀剂的脱除效能。
在制造半导体器件时,通常是在室温至150℃下采用本发明光致抗蚀剂脱除剂实施光致抗蚀剂的脱除的。由于本发明光致抗蚀剂脱除剂可在低至70℃或70℃以下的温度下脱除光致抗蚀剂,因而可有效地避免对半导体材料的不利影响。
本发明光致抗蚀剂脱除剂适用于制造由各种材料构成的半导体器件时脱除光致抗蚀剂。这类材料的实例包括硅、无定形硅、多晶硅、氧化硅、四氮化三硅、铜、铜合金、铝、铝合金、金、铂、银、钛、钛-钨、氮化钛、钨、钽、钽化物、铬、氧化铬、铬合金、半导体线材(如铟-锡-氧化物(ITO))、化合物半导体(如镓-砷、镓-磷和铟-磷)、介电材料(如锶-铋-钽)以及用于LCD基体的玻璃。
在制造半导体器件时采用本发明光致抗蚀剂脱除剂脱除光致抗蚀剂是按下述方法实施的。将光致抗蚀剂组合物涂敷在形成于基体上的导电层上以形成光致抗蚀剂层,并通过曝光和显影构图。然后,以经构图后的光致抗蚀剂层为掩膜对导电层中非掩蔽区域进行蚀刻。其后,使经蚀刻的基体与光致抗蚀剂脱除剂相接触,以除去剩下的光致抗蚀剂层。根据需要,经蚀刻后的剩下的光致抗蚀剂层可经受磨光处理,然后,采用光致抗蚀剂脱除剂去除光致抗蚀剂残留物。去除光致抗蚀剂层或光致抗蚀剂残留物后,可用有机溶剂如乙醇或水对基体进行漂洗。
下面将参照下列实施例对本发明作更详细的说明,但不应认为这些实施例是对本发明范围的限制。
合成实施例1
甲醛-单乙醇胺缩合物的制备
(醛/胺=0.5摩尔比)
在溶液温度为70℃或低于70℃的条件下,借助搅拌,缓慢地将15克多聚甲醛添加到61.0克单乙醇胺中,由此制得呈溶液状态的反应产物A。所有反应步骤都在氮气流中进行。反应产物A的13C-NMR谱图(DMSO-d6)图示于图1中。在图1中,EA表示单乙醇胺,mlEA表示羟甲基乙醇胺,FEA表示甲醛-单乙醇胺反应产物。
合成实施例2
甲醛-单乙醇胺缩合物的制备
(醛/胺=0.8摩尔比)
在溶液温度为70℃或低于70℃的条件下,借助搅拌,缓慢地将24克多聚甲醛添加到61.0克单乙醇胺中,由此制得呈溶液状态的反应产物A。所有反应步骤都在氮气流中进行。
实施例1-5和对照实施例1-2
用光致抗蚀剂PFR-7900对表面预先经硅化合物处理过的6英寸硅晶片进行旋涂。经160℃烘烤,制得光致抗蚀剂涂层厚度为10000埃的基体。
将上述制得的基体分别浸入表1所列的50℃下的光致抗蚀剂脱除剂中。经预先设定的时间后,取出各基体,用水漂洗,用氮气吹干,然后在光学显微镜下观察,以确定除去光致抗蚀剂层所需时间。结果列于表1中。
表1
烷醇胺 甲醛-烷醇胺反应产物 溶剂 除去光致抗蚀
种类 wt% 种类 wt% 种类 wt% 剂所需时间
实施例
1 EA 65 反应产物A 5 DMSO 30 20s
2 EA 65 反应产物A 5 DMAC 30 20s
3 EA 65 反应产物B 5 DMSO 30 30s
4 EA 66.5 反应产物B 3.5 DMSO 30 40s
5 EA 69 反应产物A 1 DMSO 30 60s
对照实施例
1 EA 70 - - DMSO 30 180s
2 EA 69 mlEA 1 DMSO 30 120s
EA:单乙醇胺
DMAC:二甲基乙酰胺
DMSO:二甲亚砜
mlEA:羟甲基乙醇胺
实施例6-9和对照实施例3-4
将二氧化碳气体通入68.5克单乙醇胺与30克DMSO的混合溶液中以溶入1.5克二氧化碳,所得液体称为“二氧化碳劣化脱除液”。将表2所列的每种添加剂添加到二氧化碳劣化脱除液中后,按与实施例1-5相同的方法进行脱除光致抗蚀剂试验。试验结果列于表2中。
表2
添加剂 除去光致抗蚀剂所需时间
种类 wt%
实施例
6 反应产物A 5 30s
7 反应产物A 2.5 60s
8 反应产物A 1.25 90s
9 反应产物A 5 30s
柠檬酸 1
对照实施例
3 - - 240s
4 柠檬酸 1 240s
买施例10
除了将多聚甲醛换成32%福尔马林外,其余重复合成实施例1的制备步骤制备甲醛-单乙醇胺反应产物。按与实施例1相同的方法,采用由此制备的甲醛-单乙醇胺反应产物进行光致抗蚀剂脱除试验。在浸入20秒钟后,光致抗蚀剂层被完全除去。
实施例11
除了将单乙醇胺换成异丙醇胺外,其余重复合成实施例1的制备步骤制备甲醛-异丙醇胺反应产物。按与实施例1相同的方法,采用由此制备的甲醛-单乙醇胺反应产物进行光致抗蚀剂脱除试验。在浸入20秒钟后,光致抗蚀剂层被完全除去。
实施例12
在30克二甲基亚砜中,使1克多聚甲醛与69克单乙醇胺(醛/胺=0.03摩尔比)进行反应,以制备含甲醛-单乙醇胺反应产物的溶液。按与实施例1相同的方法,采用由此制备的溶液进行光致抗蚀剂脱除试验。在浸入30秒钟后,光致抗蚀剂层被完全除去。
实施例13
腐蚀试验
将覆有铝层的无定形硅(a-Si)基体浸入实施例3-7的、温度为70℃的光致抗蚀剂脱除剂中,持续30分钟后,分别采用光学厚度计和萤光X射线测定a-Si和Al的浸蚀速率。结果显示,a-Si和Al的浸蚀速率都是5埃/分钟或以下。
本发明的光致抗蚀剂脱除剂能在短时间内除去光致抗蚀剂层和光致抗蚀剂残留物而不会对基体、导线材料等产生腐蚀作用。此外,本发明光致抗蚀剂脱除剂不会因吸收二氧化碳气体而损害脱除光致抗蚀剂的效能。
Claims (13)
1.一种光致抗蚀剂脱除剂,该脱除剂包含由摩尔比为0.8或低于0.8的甲醛与烷醇胺进行反应得到的反应产物。
2.根据权利要求1的光致抗蚀剂脱除剂,其中烷醇胺是至少一种选自乙醇胺、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、异丙醇胺、N-甲基异丙醇胺、N-乙基异丙醇胺、N-丙基异丙醇胺、2-氨基丙烷-1-醇、N-甲基-2-氨基丙烷-1-醇和N-乙基-2-氨基丙烷-1-醇的化合物。
3.根据权利要求1或2的光致抗蚀剂脱除剂,还包含碱化合物。
4.根据权利要求3的光致抗蚀剂脱除剂,其中碱化合物是至少一种选自烷基胺、烷醇胺、多胺、环胺、季铵盐和羟胺化合物的化合物。
5.根据权利要求1-4任一项的光致抗蚀剂脱除剂,还包含有机溶剂。
6.根据权利要求5的光致抗蚀剂脱除剂,其中有机溶剂是至少一种选自醚溶剂、酰胺溶剂、醇溶剂、亚砜溶剂、砜溶剂、咪唑啉酮溶剂和内酯溶剂的溶剂。
7.根据权利要求1-6任一项的光致抗蚀剂脱除剂,还包含防腐蚀剂。
8.根据权利要求7的光致抗蚀剂脱除剂,其中防腐蚀剂是至少一种选自芳族羟基化合物、糖醇、三唑化合物和螯合化合物的化合物。
9.根据权利要求1-8任一项的光致抗蚀剂脱除剂,还包含水。
10.根据权利要求1-9任一项的光致抗蚀剂脱除剂,该脱除剂包含0.001-100重量%甲醛与烷醇胺的反应产物,以及至少一种任选的选自碱化合物0-99.999重量%、有机溶剂0-99重量%、防腐蚀剂0.1-30重量%和水1-50重量%的成分,选自各对应范围的各百分比的总量达100重量%。
11.根据权利要求1-10任一项的光致抗蚀剂脱除剂,其中甲醛与烷醇胺的反应产物是甲醛-单乙醇胺缩合物或甲醛-异丙醇胺缩合物。
12.根据权利要求1-11任一项的光致抗蚀剂脱除剂,其中甲醛与烷醇胺的反应产物是按下述方法制得的,该方法包括:
在反应溶液温度为70℃或低于70℃的条件下,借助搅拌,在30-1200分钟内将甲醛缓慢地添加到预定量的烷醇胺中的步骤;和
在反应溶液温度为70℃或低于70℃下,再搅拌反应溶液30-1200分钟的任选步骤,各步骤都是在惰性气体气氛中进行的。
13.根据权利要求1-12任一项的光致抗蚀剂脱除剂,其中甲醛与烷醇胺的反应产物的13C-NMR(DMSO-d6)谱图显示出至少在45-50、61-62和64-70ppm的峰。
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2004
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- 2004-01-05 SG SG200400024-6A patent/SG135013A1/en unknown
- 2004-01-08 TW TW093100399A patent/TWI327751B/zh not_active IP Right Cessation
- 2004-01-09 KR KR1020040001351A patent/KR101085255B1/ko active IP Right Grant
- 2004-01-09 CN CNB2004100020764A patent/CN100472331C/zh not_active Expired - Lifetime
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2006
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CN103336412A (zh) * | 2013-07-03 | 2013-10-02 | 北京科华微电子材料有限公司 | 一种新型的光刻胶剥离液及其应用工艺 |
CN106997158A (zh) * | 2016-01-22 | 2017-08-01 | 易案爱富科技有限公司 | 光刻胶去除用剥离液组合物 |
WO2018099112A1 (zh) * | 2016-11-29 | 2018-06-07 | 安集微电子科技(上海)股份有限公司 | 一种含氟清洗液 |
CN110383179A (zh) * | 2018-02-14 | 2019-10-25 | 默克专利股份有限公司 | 光刻胶去除剂组合物 |
CN110383179B (zh) * | 2018-02-14 | 2021-10-29 | 默克专利股份有限公司 | 光刻胶去除剂组合物 |
CN115236953A (zh) * | 2021-04-22 | 2022-10-25 | 金�雄 | 用于去除光致抗蚀剂的剥离剂组合物及使用其的光致抗蚀剂的剥离方法 |
Also Published As
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KR20040064234A (ko) | 2004-07-16 |
CN100472331C (zh) | 2009-03-25 |
KR101085255B1 (ko) | 2011-11-22 |
SG135013A1 (en) | 2007-09-28 |
US20040137379A1 (en) | 2004-07-15 |
TW200416864A (en) | 2004-09-01 |
JP4085262B2 (ja) | 2008-05-14 |
TWI327751B (en) | 2010-07-21 |
JP2004219486A (ja) | 2004-08-05 |
US20060270574A1 (en) | 2006-11-30 |
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