CN101482698A - 抗蚀剂组合物 - Google Patents
抗蚀剂组合物 Download PDFInfo
- Publication number
- CN101482698A CN101482698A CNA2008100022560A CN200810002256A CN101482698A CN 101482698 A CN101482698 A CN 101482698A CN A2008100022560 A CNA2008100022560 A CN A2008100022560A CN 200810002256 A CN200810002256 A CN 200810002256A CN 101482698 A CN101482698 A CN 101482698A
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- China
- Prior art keywords
- acid
- group
- ester
- acetoxyl group
- organic solvent
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 43
- -1 ester compound Chemical group 0.000 claims abstract description 253
- 239000003960 organic solvent Substances 0.000 claims abstract description 45
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 42
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 39
- 150000002148 esters Chemical class 0.000 claims abstract description 27
- 239000002253 acid Substances 0.000 claims description 36
- 150000001875 compounds Chemical group 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 14
- 125000005587 carbonate group Chemical group 0.000 claims description 11
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 7
- 125000005907 alkyl ester group Chemical group 0.000 claims description 4
- 235000011090 malic acid Nutrition 0.000 claims description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 4
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical group 0.000 abstract description 14
- 238000002360 preparation method Methods 0.000 abstract description 7
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 33
- 229920005989 resin Polymers 0.000 description 29
- 239000011347 resin Substances 0.000 description 29
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 29
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 19
- 238000000576 coating method Methods 0.000 description 17
- 229940070710 valerate Drugs 0.000 description 16
- 239000003513 alkali Substances 0.000 description 15
- 239000011248 coating agent Substances 0.000 description 15
- ROBFUDYVXSDBQM-UHFFFAOYSA-N Hydroxypropanedioic acid Natural products OC(=O)C(O)C(O)=O ROBFUDYVXSDBQM-UHFFFAOYSA-N 0.000 description 13
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 229960003328 benzoyl peroxide Drugs 0.000 description 10
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 10
- TZRXHJWUDPFEEY-UHFFFAOYSA-N Pentaerythritol Tetranitrate Chemical compound [O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O TZRXHJWUDPFEEY-UHFFFAOYSA-N 0.000 description 9
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 8
- OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 8
- 239000012530 fluid Substances 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 8
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 229940017219 methyl propionate Drugs 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 229940100539 dibutyl adipate Drugs 0.000 description 6
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 6
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 6
- 230000003014 reinforcing effect Effects 0.000 description 6
- 230000035945 sensitivity Effects 0.000 description 6
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 5
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N beta-hydroxy propionic acid Natural products OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 5
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 229960002097 dibutylsuccinate Drugs 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 5
- HNBDRPTVWVGKBR-UHFFFAOYSA-N n-pentanoic acid methyl ester Natural products CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 5
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 4
- UHOPWFKONJYLCF-UHFFFAOYSA-N 2-(2-sulfanylethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCS)C(=O)C2=C1 UHOPWFKONJYLCF-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 239000001384 succinic acid Substances 0.000 description 4
- QCYFOZWGXKXDJA-UHFFFAOYSA-N 1-butoxyhexane Chemical compound CCCCCCOCCCC QCYFOZWGXKXDJA-UHFFFAOYSA-N 0.000 description 3
- ZXHQLEQLZPJIFG-UHFFFAOYSA-N 1-ethoxyhexane Chemical compound CCCCCCOCC ZXHQLEQLZPJIFG-UHFFFAOYSA-N 0.000 description 3
- HFZLSTDPRQSZCQ-UHFFFAOYSA-N 1-pyrrolidin-3-ylpyrrolidine Chemical compound C1CCCN1C1CNCC1 HFZLSTDPRQSZCQ-UHFFFAOYSA-N 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- ICBJCVRQDSQPGI-UHFFFAOYSA-N Methyl hexyl ether Chemical compound CCCCCCOC ICBJCVRQDSQPGI-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000006226 butoxyethyl group Chemical group 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 3
- 238000010894 electron beam technology Methods 0.000 description 3
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 229940079877 pyrogallol Drugs 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- ZSDQQJHSRVEGTJ-UHFFFAOYSA-N 2-(6-amino-1h-indol-3-yl)acetonitrile Chemical compound NC1=CC=C2C(CC#N)=CNC2=C1 ZSDQQJHSRVEGTJ-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- APWRLAZEMYLHKZ-UHFFFAOYSA-N 2-amino-5,6-dimethyl-1h-pyrimidin-4-one Chemical compound CC=1NC(N)=NC(=O)C=1C APWRLAZEMYLHKZ-UHFFFAOYSA-N 0.000 description 2
- UDLOAJGWSDUKME-UHFFFAOYSA-N 2-butoxybutanedioic acid Chemical compound CCCCOC(C(O)=O)CC(O)=O UDLOAJGWSDUKME-UHFFFAOYSA-N 0.000 description 2
- FJSIWMCYLGDOIV-UHFFFAOYSA-N 2-butoxypentanedioic acid Chemical compound C(CCC)OC(C(=O)O)CCC(=O)O FJSIWMCYLGDOIV-UHFFFAOYSA-N 0.000 description 2
- INBFFHSPRJSUNX-UHFFFAOYSA-N 2-butoxypropanedioic acid Chemical compound C(CCC)OC(C(=O)O)C(=O)O INBFFHSPRJSUNX-UHFFFAOYSA-N 0.000 description 2
- GDXKLPSQGLQURU-UHFFFAOYSA-N 2-ethoxybutanedioic acid Chemical compound CCOC(C(O)=O)CC(O)=O GDXKLPSQGLQURU-UHFFFAOYSA-N 0.000 description 2
- XGJBQTOLANVTEK-UHFFFAOYSA-N 2-ethoxypentanedioic acid Chemical compound CCOC(C(O)=O)CCC(O)=O XGJBQTOLANVTEK-UHFFFAOYSA-N 0.000 description 2
- HWXBTNAVRSUOJR-UHFFFAOYSA-N 2-hydroxyglutaric acid Chemical compound OC(=O)C(O)CCC(O)=O HWXBTNAVRSUOJR-UHFFFAOYSA-N 0.000 description 2
- GTWJUDXIBMRDNK-UHFFFAOYSA-N 2-methoxybutanedioic acid Chemical compound COC(C(O)=O)CC(O)=O GTWJUDXIBMRDNK-UHFFFAOYSA-N 0.000 description 2
- WTTQDTBVPMPXRL-UHFFFAOYSA-N 2-methoxypentanedioic acid Chemical compound COC(C(O)=O)CCC(O)=O WTTQDTBVPMPXRL-UHFFFAOYSA-N 0.000 description 2
- FUZLRTGGPPIBJQ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n-tetramethylpyrimidine-2,4-diamine Chemical compound CN(C)C1=CC=NC(N(C)C)=N1 FUZLRTGGPPIBJQ-UHFFFAOYSA-N 0.000 description 2
- LIRDIZPKBSSVBK-UHFFFAOYSA-N 3-o-ethyl 1-o-methyl propanedioate Chemical compound CCOC(=O)CC(=O)OC LIRDIZPKBSSVBK-UHFFFAOYSA-N 0.000 description 2
- YHRUNAIXGSNSTP-UHFFFAOYSA-N 5-o-ethyl 1-o-methyl pentanedioate Chemical compound CCOC(=O)CCCC(=O)OC YHRUNAIXGSNSTP-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OKJADYKTJJGKDX-UHFFFAOYSA-N Butyl pentanoate Chemical compound CCCCOC(=O)CCCC OKJADYKTJJGKDX-UHFFFAOYSA-N 0.000 description 2
- XTJFFFGAUHQWII-UHFFFAOYSA-N Dibutyl adipate Chemical compound CCCCOC(=O)CCCCC(=O)OCCCC XTJFFFGAUHQWII-UHFFFAOYSA-N 0.000 description 2
- YUXIBTJKHLUKBD-UHFFFAOYSA-N Dibutyl succinate Chemical compound CCCCOC(=O)CCC(=O)OCCCC YUXIBTJKHLUKBD-UHFFFAOYSA-N 0.000 description 2
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 2
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- HXXRQBBSGZDQNP-UHFFFAOYSA-N Ethyl methyl_succinate Chemical compound CCOC(=O)CCC(=O)OC HXXRQBBSGZDQNP-UHFFFAOYSA-N 0.000 description 2
- ICMAFTSLXCXHRK-UHFFFAOYSA-N Ethyl pentanoate Chemical compound CCCCC(=O)OCC ICMAFTSLXCXHRK-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- ROJKPKOYARNFNB-UHFFFAOYSA-N Propyl pentanoate Chemical compound CCCCC(=O)OCCC ROJKPKOYARNFNB-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- UDLOAJGWSDUKME-LURJTMIESA-N alpha-Butoxy-succinic-acid Natural products CCCCO[C@@H](CC(O)=O)C(O)=O UDLOAJGWSDUKME-LURJTMIESA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 150000001733 carboxylic acid esters Chemical group 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- ISXDVFNOXYQPIA-UHFFFAOYSA-N dibutyl pentanedioate Chemical compound CCCCOC(=O)CCCC(=O)OCCCC ISXDVFNOXYQPIA-UHFFFAOYSA-N 0.000 description 2
- NFKGQHYUYGYHIS-UHFFFAOYSA-N dibutyl propanedioate Chemical compound CCCCOC(=O)CC(=O)OCCCC NFKGQHYUYGYHIS-UHFFFAOYSA-N 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- OUWSNHWQZPEFEX-UHFFFAOYSA-N diethyl glutarate Chemical compound CCOC(=O)CCCC(=O)OCC OUWSNHWQZPEFEX-UHFFFAOYSA-N 0.000 description 2
- YSEKNCXYRGKTBJ-UHFFFAOYSA-N dimethyl 2-hydroxybutanedioate Chemical compound COC(=O)CC(O)C(=O)OC YSEKNCXYRGKTBJ-UHFFFAOYSA-N 0.000 description 2
- XTDYIOOONNVFMA-UHFFFAOYSA-N dimethyl pentanedioate Chemical compound COC(=O)CCCC(=O)OC XTDYIOOONNVFMA-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- LWIWFCDNJNZEKB-UHFFFAOYSA-N dipropyl propanedioate Chemical compound CCCOC(=O)CC(=O)OCCC LWIWFCDNJNZEKB-UHFFFAOYSA-N 0.000 description 2
- 238000001312 dry etching Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- XHEDLZYGAQSNTR-UHFFFAOYSA-N ethene;hexanedioic acid Chemical compound C=C.C=C.OC(=O)CCCCC(O)=O XHEDLZYGAQSNTR-UHFFFAOYSA-N 0.000 description 2
- 125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- 125000003800 germyl group Chemical group [H][Ge]([H])([H])[*] 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
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- 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
- G03F7/004—Photosensitive materials
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- G—PHYSICS
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0047—Photosensitive materials characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing
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- 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
- G03F7/20—Exposure; Apparatus therefor
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- 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
- G03F7/20—Exposure; Apparatus therefor
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- G03F7/2004—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light
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- Spectroscopy & Molecular Physics (AREA)
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Abstract
本发明提供一种不仅使抗蚀剂制备时的溶解性、显影时抗蚀膜粘附性的特性提高,还使抗蚀剂稳定性提高,且安全性优异的抗蚀剂组合物。该抗蚀剂组合物含有抗蚀剂成分和有机溶剂,所述有机溶剂含有选自(a)由羧酸部分的碳原子数为2~6的羟基多元羧酸酯构成的羟基多元羧酸酯化合物组、(b)由羧酸部分的碳原子数为2~6的乙酰氧基羧酸酯构成的乙酰氧基羧酸酯化合物组以及(c)由羧酸部分的碳原子数为2~6的烷氧基羧酸酯构成的烷氧基羧酸酯化合物组之中的至少1种有机溶剂。
Description
技术领域
背景技术
在集成电路、滤色器、液晶元件等的制造中要求微细加工,为了满足此要求,一直以来利用抗蚀剂。一般抗蚀剂有正型(ポジ)和负型(ネガ),通常,都是溶解在溶剂中制成溶液状态的抗蚀剂组合物。
该抗蚀剂组合物,通过旋涂、辊涂、缝涂、喷墨等公知的涂布方法在硅基板、玻璃基板等基板上涂布后,经预烘烤形成抗蚀膜,然后,对应于抗蚀剂的感光波长区域,利用紫外线、远紫外线、X射线、电子束等的粒子射线等进行曝光,显影后,根据需要实施干法蚀刻,形成所期望的抗蚀图形。
作为在上述抗蚀剂组合物中使用的溶剂,一直以来使用各种各样的溶剂,考虑溶解性、涂布性、灵敏度、显影性、形成的图案特性等来进行选择使用。例如,作为上述溶解性、涂布性、抗蚀剂形成特性等各特性均优异的溶剂,已知有乙二醇单乙基醚乙酸酯,但近年来,被指出对人体存在安全性的问题,因此渴望安全性高且树脂溶解性、引发剂溶解性优异的抗蚀剂形成特性等性能得以改善的溶剂。
作为上述问题的解决对策,示出用丙二醇单甲基醚乙酸酯等来代替乙二醇单乙基醚乙酸酯(例如专利文献1)。但是,这些与乙二醇单乙基醚乙酸酯相比安全性高的溶剂,存在抗蚀剂形成特性以及溶解性等特性不够的问题。例如丙二醇单甲基醚乙酸酯,由于抗蚀剂在基板上涂布后的膜中残留溶剂量少,导致膜厚分布异常,线宽均匀性、显影时抗蚀膜的粘附性(密性)等降低。
另外,已公开了使用β型丙二醇单甲基醚乙酸酯来改善树脂溶解性、引发剂溶解性的技术,但在树脂溶解性、引发剂溶解性方面还存在不足(例如专利文献2)。
专利文献1特开平3-1659号公报
专利文献2特公开6-324483号公报
发明内容
本发明的目的在于提供一种不仅使抗蚀剂制备时的溶解性、显影时抗蚀膜粘附性的特性提高,还使抗蚀剂稳定性提高,且安全性优异的抗蚀剂组合物。
本发明者进行了潜心研究,结果发现:通过使用特定的有机溶剂,可以达到上述目的,于是完成了本发明。
即,本发明提供一种抗蚀剂组合物,其含有抗蚀剂成分和有机溶剂,所述有机溶剂含有选自(a)由羧酸部分的碳原子数为2~6的羟基多元羧酸酯构成的羟基多元羧酸酯化合物组、(b)由羧酸部分的碳原子数为2~6的乙酰氧基羧酸酯构成的乙酰氧基羧酸酯化合物组、以及(c)由羧酸部分的碳原子数为2~6的烷氧基羧酸酯构成的烷氧基羧酸酯化合物组之中的至少1种有机溶剂。
在该抗蚀剂组合物中可以组合2种以上的有机溶剂。上述抗蚀剂组合物中,所述有机溶剂可以含有从(a′)由羧酸部分的碳原子数为2~6的羟基羧酸酯构成的羟基羧酸酯化合物组、(b)由羧酸部分的碳原子数为2~6的乙酰氧基羧酸酯构成的乙酰氧基羧酸酯化合物组、以及(c)由羧酸部分的碳原子数为2~6的烷氧基羧酸酯构成的烷氧基羧酸酯化合物组这三组化合物组中的至少两组化合物组中分别选择1种以上的多种有机溶剂。
另外,上述抗蚀剂组合物中,所述机溶剂也可以含有从由2-羟基琥珀酸二烷基酯构成的羟基多元羧酸酯化合物组、由2-乙酰氧基琥珀酸二烷基酯和2-乙酰氧基丙酸烷基酯构成的乙酰氧基羧酸酯化合物组、以及由2-甲氧基琥珀酸二烷基酯和2-甲氧基丙酸烷基酯构成的烷氧基羧酸酯化合物组这三组化合物组中的至少两组化合物组中分别选择1种以上的多种有机溶剂。
上述抗蚀剂组合物中,所述有机溶剂还可以进一步含有选自羧酸烷基酯类以及脂肪族酮类之中的至少1种溶剂。
根据本发明,可以提供使抗蚀剂制备时的溶解性提高、使抗蚀剂稳定性显著提高且在涂布抗蚀剂时通过保持抗蚀膜中的残留溶剂量来调节干燥速度、使膜厚均匀性、线宽均匀性、显影时抗蚀膜粘附性等的特性提高、且安全性高的抗蚀剂组合物。
附图说明
图1表示在截面形状评价试验中在玻璃基板与抗蚀图形的接触部分出现咬边(アンダ—カツト)现象(评价:×)的模式图。
符号说明
1 玻璃基板
2 抗蚀图形
3 咬边部
具体实施方式
在本发明中,作为有机溶剂,使用选自(a)由羧酸部分的碳原子数为2~6的羟基多元羧酸酯构成的羟基多元羧酸酯化合物组、(b)由羧酸部分的碳原子数为2~6的乙酰氧基羧酸酯构成的乙酰氧基羧酸酯化合物组、以及(c)由羧酸部分的碳原子数为2~6的烷氧基羧酸酯构成的烷氧基羧酸酯化合物组之中的至少1种有机溶剂。
这些有机溶剂除各单独使用外,还可以考虑树脂的溶解性等,将2种以上的有机溶剂混合使用。另外,也可以与上述以外的其他有机溶剂并用。作为使用2种以上的有机溶剂时的优选方式,可列举使用从(a′)由羧酸部分的碳原子数为2~6的羟基羧酸酯构成的羟基羧酸酯化合物组、(b)由羧酸部分的碳原子数为2~6的乙酰氧基羧酸酯构成的乙酰氧基羧酸酯化合物组、以及(c)由羧酸部分的碳原子数为2~6的烷氧基羧酸酯构成的烷氧基羧酸酯化合物组这3组化合物组中的至少2组化合物组中分别选择1种以上的多种有机溶剂。其中,优选上述烷氧基羧酸酯化合物组中含有的有机溶剂和乙酰氧基羧酸酯化合物组中含有的有机溶剂的混合体系。
在上述(a′)、(b)、(c)中,“羧酸部分的碳原子数为2~6的羟基羧酸酯”指碳原子数2~6的羧酸的酯中在羧酸部分的碳原子上连有1个或2个以上(优选1个)羟基的化合物,“羧酸部分的碳原子数为2~6的乙酰氧基羧酸酯”指碳原子数2~6的羧酸的酯中在羧酸部分的碳原子上连有1个或2个以上(优选1个)乙酰氧基的化合物,“羧酸部分的碳原子数为2~6的烷氧基羧酸酯”指碳原子数2~6的羧酸的酯中在羧酸部分的碳原子上连有1个或2个以上(优选1个)烷氧基的化合物。作为上述(a′)、(b)、(c)中的“羧酸”,优选脂肪族羧酸或脂环式羧酸,其中,优选脂肪族羧酸(特别是脂肪族饱和羧酸)。“羧酸”可以是单羧酸,也可以是二羧酸、三羧酸等多元羧酸。作为上述(a′)、(b)、(c)中的“酯”,优选烷基酯,其中优选甲酯、乙酯、丙酯、丁酯等碳原子数1~4的烷基酯。羧酸的羧基优选全部酯化。作为上述(c)中的“烷氧基”,优选碳原子数1~6的烷氧基,其中,优选甲氧基、乙氧基、丙氧基、丁氧基等碳原子数1~4的烷氧基。上述(a)中“羧酸部分的碳原子数为2~6的羟基多元羧酸酯”是(a′)的“羧酸部分的碳原子数为2~6的羟基羧酸酯”中羧酸部分为多元羧酸的化合物。
作为(a)中的羧酸部分的碳原子数为2~6的羟基多元羧酸酯,可列举例如羟基丙二酸二甲酯、羟基丙二酸二乙酯、羟基丙二酸二丙酯、羟基丙二酸二丁酯、羟基丙二酸甲乙酯、羟基丙二酸甲丙酯、羟基丙二酸甲丁酯等羟基丙二酸二酯;羟基琥珀酸二甲酯、羟基琥珀酸二乙酯、羟基琥珀酸二丙酯、羟基琥珀酸二丁酯、羟基琥珀酸甲乙酯、羟基琥珀酸甲丙酯、羟基琥珀酸甲丁酯等羟基琥珀酸二酯;羟基戊二酸二甲酯、羟基戊二酸二乙酯、羟基戊二酸二丙酯、羟基戊二酸二丁酯、羟基戊二酸甲乙酯、羟基戊二酸甲丙酯、羟基戊二酸甲丁酯等羟基戊二酸二酯(2-羟基戊二酸二酯、3-羟基戊二酸二酯);羟基己二酸二甲酯、羟基己二酸二乙酯、羟基己二酸二丙酯、羟基己二酸二丁酯、羟基己二酸甲乙酯、羟基己二酸甲丙酯、羟基己二酸甲丁酯等羟基己二酸二酯(2-羟基己二酸二酯、3-羟基己二酸二酯、4-羟基己二酸二酯);2-羟基-1,2,3-丙三羧酸三甲酯、2-羟基-1,2,3-丙三羧酸三乙酯、2-羟基-1,2,3-丙三羧酸三丙酯、2-羟基-1,2,3-丙三羧酸三丁酯、2-羟基-1,2,3-丙三羧酸二甲基乙基酯、2-羟基-1,2,3-丙三羧酸二甲基丙基酯、2-羟基-1,2,3-丙三羧酸二甲基丁基酯、2-羟基-1,2,3-丙三羧酸甲基乙基丙基酯、2-羟基-1,2,3-丙三羧酸甲基乙基丁基酯等2-羟基-1,2,3-丙三羧酸三酯等。其中,特别优选2-羟基琥珀酸二甲酯等2-羟基琥珀酸二烷基酯等羟基多元羧酸烷基酯。
作为(a′)中的羧酸部分的碳原子数为2~6的羟基羧酸酯,除上述羧酸部分的碳原子数为2~6的羟基多元羧酸酯外,还可以列举羟基乙酸甲酯、羟基乙酸乙酯、羟基乙酸丙酯、羟基乙酸丁酯等羟基乙酸酯;羟基丙酸甲酯、羟基丙酸乙酯、羟基丙酸丙酯、羟基丙酸丁酯等羟基丙酸酯(2-羟基丙酸酯、3-羟基丙酸酯);羟基丁酸甲酯、羟基丁酸乙酯、羟基丁酸丙酯、羟基丁酸丁酯等羟基丁酸酯(2-羟基丁酸酯、3-羟基丁酸酯、4-羟基丁酸酯);羟基戊酸甲酯、羟基戊酸乙酯、羟基戊酸丙酯、羟基戊酸丁酯等羟基戊酸酯(2-羟基戊酸酯、3-羟基戊酸酯、4-羟基戊酸酯、5-羟基戊酸酯)等羟基单羧酸酯(羟基单羧酸烷基酯)。
作为(b)中的羧酸部分的碳原子数为2~6的乙酰氧基羧酸酯,可列举例如乙酰氧基乙酸甲酯、乙酰氧基乙酸乙酯、乙酰氧基乙酸丙酯、乙酰氧基乙酸丁酯等乙酰氧基乙酸酯;乙酰氧基丙酸甲酯、乙酰氧基丙酸乙酯、乙酰氧基丙酸丙酯、乙酰氧基丙酸丁酯等乙酰氧基丙酸酯(2-乙酰氧基丙酸酯、3-乙酰氧基丙酸酯);乙酰氧基丁酸甲酯、乙酰氧基丁酸乙酯、乙酰氧基丁酸丙酯、乙酰氧基丁酸丁酯等乙酰氧基丁酸酯(2-乙酰氧基丁酸酯、3-乙酰氧基丁酸酯、4-乙酰氧基丁酸酯);乙酰氧基戊酸甲酯、乙酰氧基戊酸乙酯、乙酰氧基戊酸丙酯、乙酰氧基戊酸丁酯等乙酰氧基戊酸酯(2-乙酰氧基戊酸酯、3-乙酰氧基戊酸酯、4-乙酰氧基戊酸酯、5-乙酰氧基戊酸酯);乙酰氧基丙二酸二甲酯、乙酰氧基丙二酸二乙酯、乙酰氧基丙二酸二丙酯、乙酰氧基丙二酸二丁酯、乙酰氧基丙二酸甲乙酯、乙酰氧基丙二酸甲丙酯、乙酰氧基丙二酸甲丁酯等乙酰氧基丙二酸二酯;乙酰氧基琥珀酸二甲酯、乙酰氧基琥珀酸二乙酯、乙酰氧基琥珀酸二丙酯、乙酰氧基琥珀酸二丁酯、乙酰氧基琥珀酸甲乙酯、乙酰氧基琥珀酸甲丙酯、乙酰氧基琥珀酸甲丁酯等乙酰氧基琥珀酸二酯;乙酰氧基戊二酸二甲酯、乙酰氧基戊二酸二乙酯、乙酰氧基戊二酸二丙酯、乙酰氧基戊二酸二丁酯、乙酰氧基戊二酸甲乙酯、乙酰氧基戊二酸甲丙酯、乙酰氧基戊二酸甲丁酯等乙酰氧基戊二酸二酯(2-乙酰氧基戊二酸二酯、3-乙酰氧基戊二酸二酯);乙酰氧基己二酸二甲酯、乙酰氧基己二酸二乙酯、乙酰氧基己二酸二丙酯、乙酰氧基己二酸二丁酯、乙酰氧基己二酸甲乙酯、乙酰氧基己二酸甲丙酯、乙酰氧基己二酸甲丁酯等乙酰氧基己二酸二酯(2-乙酰氧基己二酸二酯、3-乙酰氧基己二酸二酯、4-乙酰氧基己二酸二酯);2-乙酰氧基-1,2,3-丙三羧酸三甲酯、2-乙酰氧基-1,2,3-丙三羧酸三乙酯、2-乙酰氧基-1,2,3-丙三羧酸三丙酯、2-乙酰氧基-1,2,3-丙三羧酸三丁酯、2-乙酰氧基-1,2,3-丙三羧酸二甲基乙基酯、2-乙酰氧基-1,2,3-丙三羧酸二甲基丙基酯、2-乙酰氧基-1,2,3-丙三羧酸二甲基丁基酯、2-乙酰氧基-1,2,3-丙三羧酸甲基乙基丙基酯、2-乙酰氧基-1,2,3-丙三羧酸甲基乙基丁基酯等2-乙酰氧基-1,2,3-丙三羧酸三酯等。其中,特别优选2-乙酰氧基丙酸甲酯等2-乙酰氧基丙酸烷基酯、2-乙酰氧基琥珀酸二甲酯等2-乙酰氧基琥珀酸二烷基酯。
作为(c)中的羧酸部分的碳原子数为2~6的烷氧基羧酸酯,可列举例如甲氧基乙酸甲酯、乙氧基乙酸甲酯、丙氧基乙酸甲酯、丁氧基乙酸甲酯、甲氧基乙酸乙酯、乙氧基乙酸乙酯、丙氧基乙酸乙酯、丁氧基乙酸乙酯、甲氧基乙酸丙酯、乙氧基乙酸丙酯、丙氧基乙酸丙酯、丁氧基乙酸丙酯、甲氧基乙酸丁酯、乙氧基乙酸丁酯、丙氧基乙酸丁酯、丁氧基乙酸丁酯等烷氧基乙酸酯;甲氧基丙酸甲酯、乙氧基丙酸甲酯、丙氧基丙酸甲酯、丁氧基丙酸甲酯、甲氧基丙酸乙酯、乙氧基丙酸乙酯、丙氧基丙酸乙酯、丁氧基丙酸乙酯、甲氧基丙酸丙酯、乙氧基丙酸丙酯、丙氧基丙酸丙酯、丁氧基丙酸丙酯、甲氧基丙酸丁酯、乙氧基丙酸丁酯、丙氧基丙酸丁酯、丁氧基丙酸丁酯等烷氧基丙酸酯;甲氧基丁酸甲酯、乙氧基丁酸甲酯、丙氧基丁酸甲酯、丁氧基丁酸甲酯、甲氧基丁酸乙酯、乙氧基丁酸乙酯、丙氧基丁酸乙酯、丁氧基丁酸乙酯、甲氧基丁酸丙酯、乙氧基丁酸丙酯、丙氧基丁酸丙酯、丁氧基丁酸丙酯、甲氧基丁酸丁酯、乙氧基丁酸丁酯、丙氧基丁酸丁酯、丁氧基丁酸丁酯等烷氧基丁酸酯;甲氧基戊酸甲酯、乙氧基戊酸甲酯、丙氧基戊酸甲酯、丁氧基戊酸甲酯、甲氧基戊酸乙酯、乙氧基戊酸乙酯、丙氧基戊酸乙酯、丁氧基戊酸乙酯、甲氧基戊酸丙酯、乙氧基戊酸丙酯、丙氧基戊酸丙酯、丁氧基戊酸丙酯、甲氧基戊酸丁酯、乙氧基戊酸丁酯、丙氧基戊酸丁酯、丁氧基戊酸丁酯等烷氧基戊酸酯;甲氧基丙二酸二甲酯、乙氧基丙二酸二甲酯、丙氧基丙二酸二甲酯、丁氧基丙二酸二甲酯、甲氧基丙二酸二乙酯、乙氧基丙二酸二乙酯、丙氧基丙二酸二乙酯、丁氧基丙二酸二乙酯、甲氧基丙二酸二丙酯、乙氧基丙二酸二丙酯、丙氧基丙二酸二丙酯、丁氧基丙二酸二丙酯、甲氧基丙二酸二丁酯、乙氧基丙二酸二丁酯、丙氧基丙二酸二丁酯、丁氧基丙二酸二丁酯、甲氧基丙二酸甲乙酯、乙氧基丙二酸甲乙酯、丙氧基丙二酸甲乙酯、丁氧基丙二酸甲乙酯、甲氧基丙二酸甲丙酯、乙氧基丙二酸甲丙酯、丙氧丙二酸甲丙酯、丁氧基丙二酸甲丙酯、甲氧基丙二酸甲丁酯、乙氧基丙二酸甲丁酯、丙氧基丙二酸甲丁酯、丁氧基丙二酸甲丁酯等烷氧基丙二酸二酯;甲氧基琥珀酸二甲酯、乙氧基琥珀酸二甲酯、丙氧基琥珀酸二甲酯、丁氧基琥珀酸二甲酯、甲氧基琥珀酸二乙酯、乙氧基琥珀酸二乙酯、丙氧基琥珀酸二乙酯、丁氧基琥珀酸二乙酯、甲氧基琥珀酸二丙酯、乙氧基琥珀酸二丙酯、丙氧基琥珀酸二丙酯、丁氧基琥珀酸二丙酯、甲氧基琥珀酸二丁酯、乙氧基琥珀酸二丁酯、丙氧基琥珀酸二丁酯、丁氧基琥珀酸二丁酯、甲氧基琥珀酸甲乙酯、乙氧基琥珀酸甲乙酯、丙氧基琥珀酸甲乙酯、丁氧基琥珀酸甲乙酯、甲氧基琥珀酸甲丙酯、乙氧基琥珀酸甲丙酯、丙氧基琥珀酸甲丙酯、丁氧基琥珀酸甲丙酯、甲氧基琥珀酸甲丁酯、乙氧基琥珀酸甲丁酯、丙氧基琥珀酸甲丁酯、丁氧基琥珀酸甲丁酯等烷氧基琥珀酸二酯;甲氧基戊二酸二甲酯、乙氧基戊二酸二甲酯、丙氧基戊二酸二甲酯、丁氧基戊二酸二甲酯、甲氧基戊二酸二乙酯、乙氧基戊二酸二乙酯、丙氧基戊二酸二乙酯、丁氧基戊二酸二乙酯、甲氧基戊二酸二丙酯、乙氧基戊二酸二丙酯、丙氧基戊二酸二丙酯、丁氧基戊二酸二丙酯、甲氧基戊二酸二丁酯、乙氧基戊二酸二丁酯、丙氧基戊二酸二丁酯、丁氧基戊二酸二丁酯、甲氧基戊二酸甲乙酯、乙氧基戊二酸甲乙酯、丙氧基戊二酸甲乙酯、丁氧基戊二酸甲乙酯、甲氧基戊二酸甲丙酯、乙氧基戊二酸甲丙酯、丙氧基戊二酸甲丙酯、丁氧基戊二酸甲丙酯、甲氧基戊二酸甲丁酯、乙氧基戊二酸甲丁酯、丙氧基戊二酸甲丁酯、丁氧基戊二酸甲丁酯等烷氧基戊二酸二酯(2-烷氧基戊二酸二酯、3-烷氧基戊二酸二酯);甲氧基己二酸二甲酯、乙氧基己二酸二甲酯、丙氧基己二酸二甲酯、丁氧基己二酸二甲酯、甲氧基己二酸二乙酯、乙氧基己二酸二乙酯、丙氧基己二酸二乙酯、丁氧基己二酸二乙酯、甲氧基己二酸二丙酯、乙氧基己二酸二丙酯、丙氧基己二酸二丙酯、丁氧基己二酸二丙酯、甲氧基己二酸二丁酯、乙氧基己二酸二丁酯、丙氧基己二酸二丁酯、丁氧基己二酸二丁酯、甲氧基己二酸甲乙酯、乙氧基己二酸甲乙酯、丙氧基己二酸甲乙酯、丁氧基己二酸甲乙酯、甲氧基己二酸甲丙酯、乙氧基己二酸甲丙酯、丙氧基己二酸甲丙酯、丁氧基己二酸甲丙酯、甲氧基己二酸甲丁酯、乙氧基己二酸甲丁酯、丙氧基己二酸甲丁酯、丁氧基己二酸甲丁酯等烷氧基己二酸二酯(2-烷氧基己二酸二酯、3-烷氧基己二酸二酯、4-烷氧基己二酸二酯);2-甲氧基-1,2,3-丙三羧酸三甲酯、2-甲氧基-1,2,3-丙三羧酸三乙酯、2-甲氧基-1,2,3-丙三羧酸三丙酯、2-甲氧基-1,2,3-丙三羧酸三丁酯、2-甲氧基-1,2,3-丙三羧酸二甲基乙基酯、2-甲氧基-1,2,3-丙三羧酸二甲基丙基酯、2-甲氧基-1,2,3-丙三羧酸二甲基丁基酯、2-甲氧基-1,2,3-丙三羧酸甲基乙基丙基酯、2-甲氧基-1,2,3-丙三羧酸甲基乙基丁基酯、2-乙氧基-1,2,3-丙三羧酸三甲酯、2-乙氧基-1,2,3-丙三羧酸三乙酯、2-乙氧基-1,2,3-丙三羧酸三丙酯、2-乙氧基-1,2,3-丙三羧酸三丁酯、2-乙氧基-1,2,3-丙三羧酸二甲基乙基酯、2-乙氧基-1,2,3-丙三羧酸二甲基丙基酯、2-乙氧基-1,2,3-丙三羧酸二甲基丁基酯、2-乙氧基-1,2,3-丙三羧酸甲基乙基丙基酯、2-乙氧基-1,2,3-丙三羧酸甲基乙基丁基酯、2-丙氧基-1,2,3-丙三羧酸三甲酯、2-丙氧基-1,2,3-丙三羧酸三乙酯、2-丙氧基-1,2,3-丙三羧酸三丙酯、2-丙氧基-1,2,3-丙三羧酸三丁酯、2-丙氧基-1,2,3-丙三羧酸二甲基乙基酯、2-丙氧基-1,2,3-丙三羧酸二甲基丙基酯、2-丙氧基-1,2,3-丙三羧酸二甲基丁基酯、2-丙氧基-1,2,3-丙三羧酸甲基乙基丙基酯、2-丙氧基-1,2,3-丙三羧酸甲基乙基丁基酯、2-丁氧基-1,2,3-丙三羧酸三甲酯、2-丁氧基-1,2,3-丙三羧酸三乙酯、2-丁氧基-1,2,3-丙三羧酸三丙酯、2-丁氧基-1,2,3-丙三羧酸三丁酯、2-丁氧基-1,2,3-丙三羧酸二甲基乙基酯、2-丁氧基-1,2,3-丙三羧酸二甲基丙基酯、2-丁氧基-1,2,3-丙三羧酸二甲基丁基酯、2-丁氧基-1,2,3-丙三羧酸甲基乙基丙基酯、2-丁氧基-1,2,3-丙三羧酸甲基乙基丁基酯等。其中,特别优选2-甲氧基丙酸甲酯等2-烷氧基丙酸烷基酯、2-甲氧基琥珀酸二甲酯等2-烷氧基琥珀酸二烷基酯。
将2种有机溶剂组合使用时,两者的比例根据溶剂的种类和目的适当选择。例如,将上述烷氧基羧酸酯化合物组中含有的有机溶剂与乙酰氧基羧酸酯化合物组中含有的有机溶剂组合使用时,两者的比例为前者/后者(重量比)=1/99~99/1,优选5/95~95/5,进一步优选10/90~90/10左右。将羟基羧酸酯化合物组中含有的有机溶剂与烷氧基羧酸酯化合物组中含有的有机溶剂组合使用,或将羟基羧酸酯化合物组中含有的有机溶剂与乙酰氧基羧酸酯化合物组中含有的有机溶剂组合使用时,优选采用与上述相同的比例。
只要不妨碍本发明的效果,在本发明的有机溶剂中还可以添加(并用)其他有机溶剂(d)。作为可添加的其他有机溶剂(d),可列举例如羧酸烷基酯类、脂肪族酮等。上述羧酸酯类中包括例如乙酸烷基酯、丙酸烷基酯等碳原子数1~4左右的脂肪族羧酸的烷基酯(例如C1-6烷基酯等)。
更具体而言,作为乙酸烷基酯,可列举乙酸丙酯、乙酸正丁酯、乙酸正戊酯等乙酸C1-6烷基酯等,作为丙酸烷基酯,可列举丙酸甲酯、丙酸乙酯、丙酸丙酯、丙酸丁酯等丙酸C1-6烷基酯等。另外,作为脂肪族酮,可列举2-丁酮、2-戊酮、2-己酮、2-庚酮等碳原子数3~10左右的脂肪族酮等。
另外,作为可添加的其他有机溶剂(d),除上述以外,还可以列举单丙二醇烷基醚、二丙二醇烷基醚等二醇醚类;单丙二醇烷基醚乙酸酯(丙二醇甲基醚乙酸酯等)等二醇醚乙酸酯类。
其他有机溶剂(d)的量可以在不损害树脂的溶解性、作为抗蚀剂用溶剂的其他特性的范围内适当选择,相对于抗蚀剂组合物中的有机溶剂总量,通常在80重量%以下,优选70重量%以下,进一步优选50重量%以下,特别优选10重量%以下,实质上也可以为0重量%。
本发明的抗蚀剂组合物中的抗蚀剂成分可以是任何以往周知或公知的正型或负型抗蚀剂。列举可以在本发明中使用的抗蚀剂的代表性物质,正型例如醌二叠氮类(キノンジアジド)感光剂和碱可溶性树脂形成的抗蚀剂、化学增强型抗蚀剂等,负型例如含有聚肉桂酸乙烯酯等感光性基团的高分子化合物的抗蚀剂、含有芳香族叠氮化合物的抗蚀剂或含有像环化橡胶和二叠氮化合物形成的叠氮化合物的抗蚀剂、含有重氮树脂的抗蚀剂、含有加成聚合性不饱和化合物的光聚合性组合物、由碱可溶性树脂和交联剂、生酸剂形成的化学增强型负型抗蚀剂等。
在本发明中,作为所使用的抗蚀剂材料的优选物质,可列举由醌二叠氮类感光剂和碱可溶性树脂形成的抗蚀剂。以往已知有多种由醌二叠氮类感光剂和碱可溶性树脂所形成的正型抗蚀剂,在本发明中均可使用,没有特殊限制。
在上述由醌二叠氮类感光剂和碱可溶性树脂所形成的正型抗蚀剂中使用的醌二叠氮类感光剂的例子,例如1,2-苯醌二叠氮-4-磺酸、1,2-萘醌二叠氮-4-磺酸、1,2-萘醌二叠氮-5-磺酸、这些磺酸的酯或酰胺等。磺酸的酯或酰胺化合物,可通过相应的醌二叠氮磺酸或醌二叠氮磺酰氯与具有羟基的化合物或具有氨基的化合物之间的缩合反应来获得。
作为具有羟基的化合物,可列举二羟基二苯甲酮、三羟基二苯甲酮、四羟基二苯甲酮、苯酚、萘酚、对甲氧基苯酚、双酚A、邻苯二酚、邻苯三酚、邻苯三酚甲基醚、没食子酸、α,α′,α″-三(4-羟基苯基)-1,3,5-三异丙基苯、三(羟基苯基)甲烷等,另外,作为具有氨基的化合物,可列举苯胺、对氨基二苯基胺等。这些醌二叠氮类感光剂可以单独或作为2种以上的混合物使用。
另一方面,作为碱可溶性树脂,可列举例如酚醛清漆树脂(ノボラツク樹脂)、聚乙烯基苯酚(ポリビニルフエノ—ル)、聚乙烯醇、丙烯酸或甲基丙烯酸的共聚物等。
作为酚醛清漆树脂,可列举例如苯酚、邻甲酚、间甲酚、对甲酚、二甲酚、三甲基苯酚、叔丁基苯酚、乙基苯酚、2-萘酚、1.3-二羟基萘等酚类中的1种或2种以上与甲醛、多聚甲醛等醛类的缩聚产物。上述酚醛清漆树脂等碱可溶性树脂,根据需要,可以2种以上组合使用,此外,为了改善被膜形成性等,还可以添加其他树脂。另外,作为醌二叠氮磺酸酯,也可以使用酚类和醛类或酮类的缩聚物与醌二叠氮磺酸的酯。
关于上述醌二叠氮类感光剂和碱可溶性树脂的使用比例,根据具体使用的感光剂和碱可溶性树脂的不同而不同,通常按重量比优选为1:1~1:20的范围,但本发明不限于此。
另外,化学增强型抗蚀剂也是可以在本发明中优选使用的正型抗蚀剂。该化学增强型抗蚀剂,通过放射线照射产生酸,在该酸的催化作用下,引起化学变化,从而改变放射线照射部分对显影液的溶解性而形成图形,例如化学增强型抗蚀剂,其包含通过放射线照射产生酸的酸发生化合物和在酸的存在下分解产生酚羟基或羧基这样的碱可溶性基团的含酸感应性基团树脂。
作为上述通过放射线照射而产生酸的酸发生化合物,可列举二(异丙基磺酰基)重氮甲烷这样的二磺酰基重氮甲烷类、甲磺酰基对甲苯磺酰基甲烷这样的二磺酰基甲烷类、环己基磺酰基环己基羰基重氮甲烷这样的磺酰基羰基重氮甲烷类、2-甲基-2-(4-甲基苯基磺酰基)苯丙酮这样的磺酰基羰基烷类、2-硝基苄基对甲苯磺酸酯这样的磺酸硝基苄基酯类、邻苯三酚三甲磺酸酯这样的磺酸烷基或芳基酯类、对甲苯磺酸酯(ベンソイントシレ—ト)这样的苯偶姻磺酸酯类、N-(三氟甲基磺酰氧基)邻苯二甲酰亚胺这样的N-磺酰氧基酰亚胺类、(4-氟-苯磺酰氧基)-3,4,6-三甲基-2-吡啶酮这样的吡咯烷酮类、2,2,2-三氟-1-三氟甲基-1-(3-乙烯基苯基)-乙基4-氯苯磺酸酯这样的磺酸酯类、甲磺酸三苯基锍鎓这样的鎓盐类等,这些化合物可以单独或2种以上混合使用。
另外,在酸的存在下分解产生酚羟基或羧基这样的碱可溶性基团的含酸感应性基团树脂,包括在酸的存在下分解的酸感应性基团和具有碱可溶性基团的碱可溶性树脂部。作为上述酸感应性基团,可列举苄基这样的取代甲基、1-甲氧基乙基、1-苄氧基乙基等1-取代乙基、叔丁基等1-支链烷基、三甲基甲硅烷基等甲硅烷基、三甲基甲锗烷基等甲锗烷基、叔丁氧基羰基等烷氧基羰基、乙酰基等酰基、四氢吡喃基、四氢呋喃基、四氢硫代吡喃基、四氢硫代呋喃基等环式酸分解基团等。这些酸分解性基团中优选苄基、叔丁基、叔丁氧基羰基、四氢吡喃基、四氢呋喃基、四氢硫代吡喃基、四氢硫代呋喃基等。
作为具有酚羟基或羧基这样的碱可溶性基团的碱可溶性树脂,可列举羟基苯乙烯、羟基-α-甲基苯乙烯、羟基甲基苯乙烯、羟基金刚烷基(甲基)丙烯酸酯、羧基金刚烷基(甲基)丙烯酸酯、乙烯基苯甲酸、羧基甲基苯乙烯、羧基甲氧基苯乙烯、丙烯酸、甲基丙烯酸、巴豆酸、马来酸、衣康酸、柠康酸、甲基富马酸、肉桂酸等乙烯基(ビニル)单体形成的聚合物或共聚物、这些单体中的至少1种与其他单体的共聚物、酚醛清漆树脂这样的缩聚树脂。
作为化学增强型抗蚀剂,除上述抗蚀剂外,还已知这样的抗蚀剂,其含有碱可溶性树脂、生酸剂、在酸的存在下分解并使碱可溶性树脂的溶解性控制效果降低或促进碱可溶性树脂溶解性的化合物,这样的抗蚀剂也可以使用。
上述抗蚀剂成分溶解在上述有机溶剂中可形成本发明的抗蚀剂组合物。抗蚀剂成分的比例可根据所使用的抗蚀剂的种类、溶剂的种类来适当设定,通常,相对于抗蚀剂固体成分100重量份,使用50~3000重量份、优选70~2000重量份、更优选100~1000重量份的有机溶剂。特别是当使用100~500重量份的有机溶剂时,多数情况下表现出碱可溶性树脂的高溶解性。
另外,根据使用目的,在上述抗蚀剂组合物中还可以适当配合表面活性剂、增感剂等以往公知的各种添加剂。另外,在水可溶性的情况下,也可以加水使用。
本发明的抗蚀剂组合物可以在半导体器件的制造或液晶显示元件的制造等各种用途中使用,但优选作为半导体制造用或液晶显示元件制造用的光致抗蚀剂组合物使用。关于使用本发明的抗蚀剂组合物的抗蚀图形的形成,例如如下所述那样进行。
首先,本发明的抗蚀剂组合物,通过将抗蚀剂材料溶解在上述溶剂中来制造,该制造的本发明抗蚀剂组合物,根据需要通过过滤器过滤来除去不溶物,利用旋涂法、辊涂法、逆转辊涂法、流延涂布法、刮涂法等以往公知的涂布方法在硅、玻璃等的基板上涂布,使预烘烤(プリベ—ク)后的膜厚例如为0.01~1000μm。
在基板上涂布后的抗蚀剂组合物,例如在热板上进行预烘烤而除去溶剂,形成抗蚀膜。预烘烤温度根据所使用的溶剂或抗蚀剂的种类而不同,但通常在30~200℃、优选50~150℃左右的温度下进行。
抗蚀膜形成后,进行曝光,根据所使用的抗蚀剂的不同,各感光区域也不同,因此采用与抗蚀剂的感光区域对应的曝光光源进行曝光。曝光例如使用高压汞灯、金卤灯、超高压汞灯、KrF准分子激光器、ArF准分子激光器、F2激光器、软X射线照射装置、电子束描绘装置等公知的照射装置,根据需要,通过掩膜,利用紫外线、远紫外线、X射线、电子束等进行规定的图形状的照射。曝光后,为了改善显影性、解像度、图案形状等,根据需要进行后烘烤,然后进行显影。另外,显影后,根据需要,进行气态等离子体(ガスプラズマ)等的干式蚀刻以除去防反射膜等,形成抗蚀图形。
上述抗蚀剂的显影,通常使用显影液,利用曝光区域与未曝光区域对溶剂的溶解性或对碱性溶液的溶解性的差异来进行。作为碱性显影液,使用例如氢氧化钠、氢氧化钾、碳酸钠、硅酸钠等无机碱类、氨、乙胺、二乙胺、三乙胺、二乙醇胺、三乙醇胺、苄胺等胺类、甲酰胺等酰胺类、四甲基氢氧化铵(TMAH)、四乙基氢氧化铵、胆碱等季铵盐类、吡咯、哌嗪等环状胺类等溶解形成的水溶液或水性溶液。
实施例
下面,通过实施例具体说明本发明,但本发明不限于此。
实施例1~10、比较例1~3
将2,4,4,4′-四羟基二苯甲酮1摩尔与萘醌-1,2-二叠氮-5-磺酰氯3摩尔的酯化反应产物2g和甲酚酚醛清漆树脂(クレゾ—ルノボラツク樹脂)8g溶解在表1所示的组成的溶剂(数字为重量比)40g中,制备正型光致抗蚀剂组合物的涂布液。对按上述操作得到的涂布液进行以下(1)~(4)的评价试验。结果如表1所示。
(1)析出物的有无
将制备的涂布液用0.2μm膜滤器过滤后的物质在40℃下静置,调查经过2个月时的涂布液中有无析出物。
(2)灵敏度变化
调查3个月后光致抗蚀剂组合物有无灵敏度变化。即,将制备后立即将涂布液涂布在基材上并使其干燥的情况与制备后经过3个月再将涂布液涂布在基材上并使其干燥的情况下的最小曝光量(灵敏度)进行比较,完全无变化的用“○”表示,灵敏度下降的用“×”表示。
(3)截面形状
将制备的涂布液在玻璃基板上进行缝涂,用热板在90℃下干燥90秒,形成膜厚为1.3μm的抗蚀膜,对于该膜,使用步进曝光装置(ステツパ—),通过规定的掩膜进行曝光,然后在热板上在110℃下加热90秒,然后用2.38重量%的四甲基氢氧化铵水溶液(TMAH)显影,观察30秒水洗·干燥得到的抗蚀图形的截面形状,按以下基准进行评价。
○:玻璃基板与抗蚀图形的接触部分未出现咬边
×:玻璃基板与抗蚀图形的接触部分出现咬边(参照图1)
(4)涂布状态
将制备的涂布液在玻璃基板上进行缝涂,用热板在90℃下干燥90秒,测定形成的膜厚,将能在面内均匀涂布的评价为“良好”,无法在面内均匀涂布的评价为“不良”。
表1
溶剂(混合重量比) | 析出物的有无 | 灵敏度变化 | 截面形状 | 涂布状态 | |
实施例1 | SMH=100 | 无 | ○ | ○ | 良好 |
实施例2 | SMHA=100 | 无 | ○ | ○ | 良好 |
实施例3 | PMHA=100 | 无 | ○ | ○ | 良好 |
实施例4 | SMHM=100 | 无 | ○ | ○ | 良好 |
实施例5 | PMHM=100 | 无 | ○ | ○ | 良好 |
实施例6 | SMH:SMHA=50:50 | 无 | ○ | ○ | 良好 |
实施例7 | SMHA:SMHM=70:30 | 无 | ○ | ○ | 良好 |
实施例8 | PMHM:PMHA=60:40 | 无 | ○ | ○ | 良好 |
实施例9 | SMHA:PGMEA=80:20 | 无 | ○ | ○ | 良好 |
实施例10 | PMHA:PGMEA=40:60 | 无 | ○ | ○ | 良好 |
比较例1 | PGMEA=100 | 有 | ○ | × | 不良 |
比较例2 | 环戊酮=100 | 无 | × | × | 不良 |
比较例3 | EL=100 | 有 | ○ | × | 不良 |
表中的缩写分别如下所述。
SMH:2-羟基琥珀酸二甲酯
SMHA:2-乙酰氧基琥珀酸二甲酯
PMHA:2-乙酰氧基丙酸甲酯
SMHM:2-甲氧基琥珀酸二甲酯
PMHM:2-甲氧基丙酸甲酯
PGMEA:丙二醇甲基醚乙酸酯
EL:乳酸乙酯
实施例11~12、比较例4
使单羟基金刚烷基丙烯酸酯和四氢吡喃基甲基丙烯酸酯共聚,得到单羟基金刚烷基丙烯酸酯单元70mol%和四氢吡喃基甲基丙烯酸酯单元30mol%的重均分子量为8000的共聚物。添加表2所述组成的溶剂,使所得到的树脂中的固体成分为25重量%,在50℃下加热10分钟,观察树脂的溶解速度(溶解性)。结果如表2所示。表中的缩写与上述相同。
○:形成均匀的透明溶液
×:器壁上残留粒状不溶树脂
表2
溶剂(混合重量比) | 树脂溶解性 | |
实施例11 | PMHA=100 | ○ |
实施例12 | SMHA:EL=70:30 | ○ |
比较例4 | PGMEA=100 | × |
本发明的抗蚀剂组合物由于溶剂溶解性优异、对人体安全且稳定性优异,因此可作为半导体器件和液晶显示元件等的制造中使用的光致抗蚀剂组合物有用。
Claims (4)
1.抗蚀剂组合物,其含有抗蚀剂成分和有机溶剂,所述有机溶剂含有选自(a)由羧酸部分的碳原子数为2~6的羟基多元羧酸酯构成的羟基多元羧酸酯化合物组、(b)由羧酸部分的碳原子数为2~6的乙酰氧基羧酸酯构成的乙酰氧基羧酸酯化合物组、以及(c)由羧酸部分的碳原子数为2~6的烷氧基羧酸酯构成的烷氧基羧酸酯化合物组之中的至少1种有机溶剂。
2.权利要求1的抗蚀剂组合物,其中所述有机溶剂含有从(a′)由羧酸部分的碳原子数为2~6的羟基羧酸酯构成的羟基羧酸酯化合物组、(b)由羧酸部分的碳原子数为2~6的乙酰氧基羧酸酯构成的乙酰氧基羧酸酯化合物组、以及(c)由羧酸部分的碳原子数为2~6的烷氧基羧酸酯构成的烷氧基羧酸酯化合物组这三组化合物组中的至少两组化合物组中分别选择1种以上的多种有机溶剂。
3.如权利要求1的抗蚀剂组合物,其中所述有机溶剂含有从由2-羟基琥珀酸二烷基酯构成的羟基多元羧酸酯化合物组、由2-乙酰氧基琥珀酸二烷基酯和2-乙酰氧基丙酸烷基酯构成的乙酰氧基羧酸酯化合物组、以及由2-甲氧基琥珀酸二烷基酯和2-甲氧基丙酸烷基酯构成的烷氧基羧酸酯化合物组这三组化合物组中的至少两组化合物组中分别选择1种以上的多种有机溶剂。
4.如权利要求1~3任一项的抗蚀剂组合物,其中所述有机溶剂进一步含有选自羧酸烷基酯类以及脂肪族酮类之中的至少1种溶剂。
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