KR19990007372A - 레지스트 재료 - Google Patents
레지스트 재료 Download PDFInfo
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- KR19990007372A KR19990007372A KR1019980024358A KR19980024358A KR19990007372A KR 19990007372 A KR19990007372 A KR 19990007372A KR 1019980024358 A KR1019980024358 A KR 1019980024358A KR 19980024358 A KR19980024358 A KR 19980024358A KR 19990007372 A KR19990007372 A KR 19990007372A
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- South Korea
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- 239000000463 material Substances 0.000 title claims abstract description 46
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 84
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 47
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 44
- 150000007514 bases Chemical class 0.000 claims abstract description 28
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 22
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 10
- 125000003277 amino group Chemical group 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims description 62
- 229920005989 resin Polymers 0.000 claims description 48
- 239000011347 resin Substances 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 19
- 239000002585 base Substances 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 239000003960 organic solvent Substances 0.000 claims description 16
- 238000004090 dissolution Methods 0.000 claims description 13
- 239000003513 alkali Substances 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 238000004132 cross linking Methods 0.000 claims description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 8
- 230000009471 action Effects 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000005188 oxoalkyl group Chemical group 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- 230000000694 effects Effects 0.000 abstract description 18
- 230000009467 reduction Effects 0.000 abstract description 7
- 238000002955 isolation Methods 0.000 abstract description 3
- -1 pyridine compound Chemical class 0.000 description 97
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 77
- 150000001412 amines Chemical class 0.000 description 26
- 239000000203 mixture Substances 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 14
- 239000000758 substrate Substances 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 150000002430 hydrocarbons Chemical group 0.000 description 9
- 125000003710 aryl alkyl group Chemical group 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
- 239000004593 Epoxy Substances 0.000 description 6
- 229920000877 Melamine resin Polymers 0.000 description 6
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 6
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 4
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 4
- 125000005011 alkyl ether group Chemical group 0.000 description 4
- 238000013329 compounding Methods 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000005011 phenolic resin Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 229960004418 trolamine Drugs 0.000 description 4
- LJHFIVQEAFAURQ-ZPUQHVIOSA-N (NE)-N-[(2E)-2-hydroxyiminoethylidene]hydroxylamine Chemical class O\N=C\C=N\O LJHFIVQEAFAURQ-ZPUQHVIOSA-N 0.000 description 3
- UVCUTACRFCJVPW-UHFFFAOYSA-N 1-(chloromethoxymethoxy)-2-methoxyethane Chemical compound COCCOCOCCl UVCUTACRFCJVPW-UHFFFAOYSA-N 0.000 description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 3
- 239000004971 Cross linker Substances 0.000 description 3
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical class C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000004640 Melamine resin Substances 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
- 229920001807 Urea-formaldehyde Polymers 0.000 description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 description 3
- 229940061627 chloromethyl methyl ether Drugs 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229940116333 ethyl lactate Drugs 0.000 description 3
- 238000001459 lithography Methods 0.000 description 3
- 235000012054 meals Nutrition 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 3
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 230000007261 regionalization Effects 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- WNQSKPOIYILBMI-UHFFFAOYSA-N 1-[butylsulfonyl(diazo)methyl]sulfonylbutane Chemical compound CCCCS(=O)(=O)C(=[N+]=[N-])S(=O)(=O)CCCC WNQSKPOIYILBMI-UHFFFAOYSA-N 0.000 description 2
- GLYOFBNLYMTEPS-UHFFFAOYSA-N 1-[diazo(2-methylpropylsulfonyl)methyl]sulfonyl-2-methylpropane Chemical compound CC(C)CS(=O)(=O)C(=[N+]=[N-])S(=O)(=O)CC(C)C GLYOFBNLYMTEPS-UHFFFAOYSA-N 0.000 description 2
- WUYAQJZXAJBVFT-UHFFFAOYSA-N 1-[diazo(propylsulfonyl)methyl]sulfonylpropane Chemical compound CCCS(=O)(=O)C(=[N+]=[N-])S(=O)(=O)CCC WUYAQJZXAJBVFT-UHFFFAOYSA-N 0.000 description 2
- GYQQFWWMZYBCIB-UHFFFAOYSA-N 1-[diazo-(4-methylphenyl)sulfonylmethyl]sulfonyl-4-methylbenzene Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1=CC=C(C)C=C1 GYQQFWWMZYBCIB-UHFFFAOYSA-N 0.000 description 2
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- YUPMMGJCVITSQO-UHFFFAOYSA-N 2-(2-methoxyethoxymethoxy)-n,n-bis[2-(2-methoxyethoxymethoxy)ethyl]ethanamine Chemical compound COCCOCOCCN(CCOCOCCOC)CCOCOCCOC YUPMMGJCVITSQO-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- NRTKFSQKHCMEMO-UHFFFAOYSA-N 2-(methoxymethoxy)-n,n-bis[2-(methoxymethoxy)ethyl]ethanamine Chemical compound COCOCCN(CCOCOC)CCOCOC NRTKFSQKHCMEMO-UHFFFAOYSA-N 0.000 description 2
- KKOOSMDBEULUDH-UHFFFAOYSA-N 2-[butan-2-ylsulfonyl(diazo)methyl]sulfonylbutane Chemical compound CCC(C)S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C(C)CC KKOOSMDBEULUDH-UHFFFAOYSA-N 0.000 description 2
- DRYBUHKBBRHEAE-UHFFFAOYSA-N 2-[diazo(propan-2-ylsulfonyl)methyl]sulfonylpropane Chemical compound CC(C)S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C(C)C DRYBUHKBBRHEAE-UHFFFAOYSA-N 0.000 description 2
- AOMKYCIOFLWFBM-UHFFFAOYSA-M 4-methylbenzenesulfonate;[4-[(2-methylpropan-2-yl)oxy]phenyl]-diphenylsulfanium Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1=CC(OC(C)(C)C)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 AOMKYCIOFLWFBM-UHFFFAOYSA-M 0.000 description 2
- MJGQMEJOQAULGB-UHFFFAOYSA-M 4-methylbenzenesulfonate;tris[4-[(2-methylpropan-2-yl)oxy]phenyl]sulfanium Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1=CC(OC(C)(C)C)=CC=C1[S+](C=1C=CC(OC(C)(C)C)=CC=1)C1=CC=C(OC(C)(C)C)C=C1 MJGQMEJOQAULGB-UHFFFAOYSA-M 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- OUHCZCFQVONTOC-UHFFFAOYSA-N [3-acetyloxy-2,2-bis(acetyloxymethyl)propyl] acetate Chemical compound CC(=O)OCC(COC(C)=O)(COC(C)=O)COC(C)=O OUHCZCFQVONTOC-UHFFFAOYSA-N 0.000 description 2
- QFKJMDYQKVPGNM-UHFFFAOYSA-N [benzenesulfonyl(diazo)methyl]sulfonylbenzene Chemical compound C=1C=CC=CC=1S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1=CC=CC=C1 QFKJMDYQKVPGNM-UHFFFAOYSA-N 0.000 description 2
- GLGXSTXZLFQYKJ-UHFFFAOYSA-N [cyclohexylsulfonyl(diazo)methyl]sulfonylcyclohexane Chemical compound C1CCCCC1S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1CCCCC1 GLGXSTXZLFQYKJ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 229940106691 bisphenol a Drugs 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000001312 dry etching Methods 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 150000003459 sulfonic acid esters Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- TUODWSVQODNTSU-UHFFFAOYSA-M trifluoromethanesulfonate;tris[4-[(2-methylpropan-2-yl)oxy]phenyl]sulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(OC(C)(C)C)=CC=C1[S+](C=1C=CC(OC(C)(C)C)=CC=1)C1=CC=C(OC(C)(C)C)C=C1 TUODWSVQODNTSU-UHFFFAOYSA-M 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 2
- 238000000233 ultraviolet lithography Methods 0.000 description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
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- 238000006467 substitution reaction Methods 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000004032 superbase Substances 0.000 description 1
- 150000007525 superbases Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- AANIRNIRVXARSN-UHFFFAOYSA-M trifluoromethanesulfonate;trimethylsulfanium Chemical compound C[S+](C)C.[O-]S(=O)(=O)C(F)(F)F AANIRNIRVXARSN-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Materials For Photolithography (AREA)
Abstract
Description
실시예 | 레지스트 조성 (괄호내: 조성비 (단위: 중량부)) | 포커스 마진 (㎛) | |||||
기본 수지 | 산 발생제 | 용해 방지제 | 염기성 화합물 | 용매 | 0.18㎛ 고립 라인 | ||
구조 | 구조 | ||||||
1 | Polym.1(60) | Polym.4(20) | PAG.1(2) | - | 아민 1(0.3) | PGMEA(300) | 1.0 |
2 | Polym.1(60) | Polym.4(20) | PAG.1(2) | - | 아민 2(0.3) | PGMEA(300) | 1.0 |
3 | Polym.1(60) | Polym.4(20) | PAG.1(2) | - | 아민 3(0.3) | PGMEA(300) | 1.0 |
4 | Polym.1(60) | Polym.4(20) | PAG.1(2) | - | 아민 4(0.3) | PGMEA(300) | 1.0 |
5 | Polym.1(60) | Polym.4(20) | PAG.1(2) | - | 아민 5(0.2) | PGMEA(300) | 1.0 |
6 | Polym.1(60) | Polym.4(20) | PAG.1(2) | - | 아민 6(0.2) | PGMEA(300) | 1.0 |
7 | Polym.1(60) | Polym.4(20) | PAG.1(2) | - | 아민 7(0.4) | PGMEA(300) | 1.0 |
8 | Polym.1(60) | Polym.4(20) | PAG.1(2) | - | 아민 8(0.4) | PGMEA(300) | 0.9 |
9 | Polym.1(60) | - | PAG.1(2) | - | 아민 4(0.3) | PGMEA(300) | 0.9 |
10 | Polym.3(60) | Polym.4(20) | PAG.1(2) | - | 아민 4(0.4) | PGMEA(300) | 1.1 |
11 | Polym.1(60) | Polym.4(20) | PAG.2(2) | - | 아민 1(0.3) | PGMEA(300) | 0.9 |
12 | Polym.1(60) | Polym.4(20) | PAG.3(2) | - | 아민 1(0.3) | PGMEA(300) | 0.9 |
13 | Polym.1(60) | Polym.4(20) | PAG.1(2) | DRI.1(16) | 아민 1(0.3) | PGMEA(300) | 0.9 |
14 | Polym.1(60) | Polym.4(20) | PAG.1(2) | DRI.2(16) | 아민 1(0.3) | PGMEA(300) | 0.9 |
PGMEA: 프로필렌글리콜모노메틸에테르아세테이트 |
실시예 | 레지스트 조성 (괄호내: 조성비 (단위: 중량부)) | 포커스 마진 (㎛) | |||||
기본 수지 | 산 발생제 | 가교제 | 염기성 화합물 | 용매 | 0.18㎛ 고립 라인 | ||
구조 | 구조 | ||||||
15 | Polym.2(60) | Polym.4(20) | PAG.2(2) | - | 아민 4(0.3) | MMP(300) | 1.0 |
16 | Polym.2(60) | Polym.4(20) | PAG.2(2) | - | 아민 4(0.3) | PGMEA(210)/EL (90) | 1.0 |
17 | Polym.2(60) | Polym.4(20) | PAG.2(2) | - | 아민 4(0.3) | EL(300) | 1.0 |
18 | Polym.3(80) | - | PAG.1(2) | - | 아민 4(0.3) | PGMEA(300) | 0.8 |
19 | Polym.1(60) | Polym.4(20) | PAG.4(2) | - | 아민 4(0.3) | PGMEA(300) | 0.9 |
20 | Polym.5(80) | - | PAG.1(2) | 가교결합제 1(15) | 아민 4(0.3) | PGMEA(300) | 1.0 |
PGMEA: 프로필렌글리콜모노메틸에테르아세테이트EL: 락트산 에틸MMP: 3-메톡시프로피온산 메틸 |
실시예 | 레지스트 조성 (괄호내: 조성비 (단위: 중량부)) | 포커스 마진 (㎛) | |||||
기본 수지 | 산 발생제 | 용해 방지제 | 염기성 화합물 | 용매 | 0.18㎛ 고립 라인 | ||
구조 | 구조 | ||||||
1 | Polym.1(60) | Polym.4(20) | PAG.1(2) | - | 아민 9(0.2) | PGMEA(300) | 0.6 |
2 | Polym.1(60) | Polym.4(20) | PAG.1(2) | - | 아민 10(0.15) | PGMEA(300) | 0.6 |
3 | Polym.1(60) | Polym.4(20) | PAG.1(2) | - | 아민 11(0.15) | PGMEA(300) | 0.4 |
4 | Polym.1(60) | Polym.4(20) | PAG.1(2) | - | 아민 12(0.15) | PGMEA(300) | 0.4 |
5 | Polym.1(60) | Polym.4(20) | PAG.1(2) | - | 아민 13(0.2) | PGMEA(300) | 0.4 |
6 | Polym.1(60) | Polym.4(20) | PAG.1(2) | - | 아민 14(0.3) | PGMEA(300) | 0 |
7 | Polym.2(80) | - | PAG.1(2) | - | 아민 11(0.15) | PGMEA(300) | 0.4 |
8 | Polym.3(60) | Polym.4(20) | PAG.1(2) | - | 아민 11(0.15) | PGMEA(300) | 0.5 |
9 | Polym.1(60) | Polym.4(20) | PAG.2(2) | - | 아민 11(0.15) | PGMEA(300) | 0.4 |
10 | Polym.1(60) | Polym.4(20) | PAG.3(2) | - | 아민 11(0.15) | PGMEA(300) | 0.4 |
11 | Polym.1(60) | Polym.4(20) | PAG.1(2) | DRI.1(16) | 아민 11(0.15) | PGMEA(300) | 0.3 |
12 | Polym.1(60) | Polym.4(20) | PAG.1(2) | DRI.2(16) | 아민 11(0.15) | PGMEA(300) | 0.3 |
PGMEA: 프로필렌글리콜모노메틸에테르아세테이트 |
실시예 | 레지스트 조성 (괄호내: 조성비 (단위: 중량부)) | 포커스 마진 (㎛) | |||||
기본 수지 | 산 발생제 | 용해 방지제 또는 가교제 | 염기성 화합물 | 용매 | 0.18㎛ 고립 라인 | ||
구조 | 구조 | ||||||
13 | Polym.1(60) | Polym.4(20) | PAG.1(2) | DRI.2(16) | 아민 12(0.15) | MMP(300) | 0.4 |
14 | Polym.1(60) | Polym.4(20) | PAG.1(2) | DRI.2(16) | 아민 12(0.15) | PGMEA(210)/EL (90) | 0.4 |
15 | Polym.1(60) | Polym.4(20) | PAG.1(2) | DRI.2(16) | 아민 12(0.15) | EL(300) | 0.4 |
16 | Polym.3(80) | - | PAG.1(2) | - | 아민 11(0.15) | PGMEA(300) | 0.3 |
17 | Polym.1(60) | Polym.4(20) | PAG.4(2) | - | 아민 11(0.15) | PGMEA(300) | 0.4 |
18 | Polym.5(80) | - | PAG.1(2) | 가교결합제 1(15) | 아민 4(0.3) | PGMEA(300) | 0.4 |
PGMEA: 프로필렌글리콜모노메틸에테르아세테이트EL: 락트산 에틸MMP: 3-메톡시프로피온산 메틸 |
Claims (7)
- 하기 화학식 1 및 2로 표시되는 염기성 화합물의 1종 또는 2종 이상을 함유하는 것을 특징으로 하는 레지스트 재료.화학식 1화학식 2식 중,R1, R2, R3, R7및 R8은 각각 독립적으로 직쇄상, 분지상 또는 환상의 탄소수 1 내지 20개의 알킬렌기를 나타내고,R4, R5, R6, R9및 R10은 수소 원자, 탄소수 1 내지 20개의 알킬기 또는 아미노기를 나타내며,R4와 R5, R5와 R6, R4와 R6, R4와 R5와 R6및 R9와 R10은 각각 결합하여 환을 형성할 수도 있고,k, m 및 n은 각각 0 내지 20의 정수이나,단, k, m, n=0일 때, R4, R5, R6, R9및 R10은 수소 원자를 포함하지 않는다.
- (A) 제1항 기재의 염기성 화합물,(B) 유기 용제,(C) 산 불안정기로 보호된 산성 관능기를 갖는 알칼리 불용성 또는 난용성의 수지로서, 상기 산 불안정기가 탈리했을 때에 알칼리 가용성이 되는 기본 수지, 및(D) 산 발생제를 함유하는 것을 특징으로 하는 레지스트 재료.
- 제2항에 있어서, (C) 성분인 수지의 산 불안정기가 하기 화학식 3으로 표시되는 기, 하기 화학식 4로 표시되는 기, 탄소수 4 내지 20개의 3급 알킬기, 각 알킬기가 각각 탄소수 1 내지 6개의 트리알킬실릴기, 및 탄소수 4 내지 20개의 옥소알킬기로부터 선택되는 1종 또는 2종 이상인 레지스트 재료.화학식 3화학식 4식 중,R11및 R12는 수소 원자 또는 탄소수 1 내지 18개의 직쇄상, 분지상 또는 환상의 알킬기를 나타내고,R13은 탄소수 1 내지 18개의 헤테로 원자를 가질 수도 있는 1가의 탄화수소기를 나타내며,R11과 R12, R11과 R13및 R12와 R13은 환을 형성할 수도 있고, 환을 형성할 경우, R11, R12및 R13은 각각 탄소수 1 내지 18개의 직쇄상 또는 분지상의 알킬렌기를 나타내고,R14는 탄소수 4 내지 12개의 3급 알킬기, 각 알킬기가 각각 탄소수 1 내지 6개의 트리알킬실릴기, 탄소수 4 내지 20개의 옥소알킬기 또는 상기 화학식 3으로 표시되는 기를 나타내며,z는 0 내지 6의 정수이다.
- (A) 제1항 기재의 염기성 화합물,(B) 유기 용제,(C) 페놀성 수산기의 수소 원자 10 몰% 이상이 하기 화학식 3으로 표시되는 산 불안정기에 의해 치환되고, 또한 나머지 폐놀성 수산기의 수소 원자 0 몰%를 초과하는 비율로 하기 화학식 5a 또는 5b로 표시되는 C-O-C기를 갖는 가교기에 의해 분자내 및/또는 분자간에 가교되어 있는 중량 평균 분자량 5,000 내지 100,000의 기본 수지, 및(D) 산 발생제를 함유하는 것을 특징으로 하는 레지스트 재료.화학식 3화학식 5a화학식 5b식 중,R11및 R12는 각각 독립적으로 수소 원자 또는 탄소수 1 내지 18개의 직쇄상, 분지상 또는 환상의 알킬기를 나타내고,R13은 탄소수 1 내지 18개의 헤테로 원자를 가질 수도 있는 1가의 탄화수소기를 나타내며,R11과 R12, R11과 R13및 R12와 R13은 환을 형성할 수도 있고, 환을 형성할 경우, R11, R12및 R13은 각각 탄소수 1 내지 18개의 직쇄상 또는 분지상의 알킬렌기를 나타내고,R21및 R22는 수소 원자 또는 탄소수 1 내지 8개의 직쇄상, 분지상 또는 환상의 알킬기를 나타내거나, 또는R21과 R22는 함께 환을 형성할 수도 있고, 환을 형성할 경우, R21및 R22는 탄소수 1 내지 8개의 직쇄상 또는 분지상의 알킬렌기를 나타내고,R23은 탄소수 1 내지 10개의 직쇄상, 분지상 또는 환상의 알킬렌기를 나타내며,b는 0 또는 1 내지 10의 정수이고,A는 a가의 탄소수 1 내지 50개의 지방족 또는 지환식 포화 탄화수소기, 방향족 탄화수소기 또는 헤테로환기를 나타내며, 이들 기는 헤테로 원자를 개재할 수도 있고, 또한 그의 탄소 원자에 결합하는 수소 원자의 일부가 수산기, 카르복실기, 카르보닐기 또는 불소 원자에 의해 치환될 수도 있고,B는 -CO-O-, -NHCO-O- 또는 -NHCONH-를 나타내며,a는 2 내지 8의 정수이고,a'는 1 내지 7의 정수이다.
- (A) 제1항 기재의 염기성 화합물,(B) 유기 용제,(C) 제2, 3 또는 4항 기재의 기본 수지,(D) 산 발생제 및(E) 하기 화학식 6a로 표시되는 반복 단위를 갖는 중량 평균 분자량이 3,000 내지 300,000인 고분자 화합물을 함유하는 것을 특징으로 하는 레지스트 재료.화학식 6a식 중,R31은 수소 원자 또는 메틸기를 나타내고,R32는 수소 원자 또는 탄소수 1 내지 8개의 직쇄상, 분지상 또는 환상의 알킬기를 나타내며,R33은 -CR11R12OR13과는 상이한 산 불안정기이고,c 및 e는 0 또는 양수이며,d는 양수이나,단, c+d+e=1이고, 0.5≤d/(c+d+e)≤1.0이다.
- 제2항에 있어서, (F) 산 불안정기를 갖는 용해 저지제를 더 함유하는 것을 특징으로 하는 레지스트 재료.
- (A) 제1항 기재의 염기성 화합물,(B) 유기 용제,(G) 알칼리 가용성 수지,(D) 산 발생제, 및(H) 산의 작용에 의해 가교하는 화합물을 함유하는 것을 특징으로 하는 레지스트 재료.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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JP18581497 | 1997-06-26 | ||
JP97-185814 | 1997-06-26 |
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KR19990007372A true KR19990007372A (ko) | 1999-01-25 |
KR100539641B1 KR100539641B1 (ko) | 2006-04-21 |
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KR1019980024358A KR100539641B1 (ko) | 1997-06-26 | 1998-06-26 | 레지스트재료 |
Country Status (5)
Country | Link |
---|---|
US (1) | US6274286B1 (ko) |
EP (1) | EP0887705B1 (ko) |
KR (1) | KR100539641B1 (ko) |
DE (1) | DE69807602T2 (ko) |
TW (1) | TW526390B (ko) |
Families Citing this family (30)
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US6852466B2 (en) | 1998-12-23 | 2005-02-08 | Shipley Company, L.L.C. | Photoresist compositions particularly suitable for short wavelength imaging |
US6638684B2 (en) * | 1999-08-31 | 2003-10-28 | Tokyo Ohka Kogyo Co., Ltd. | Photosensitive laminate, process for forming resist pattern using same and positive resist composition |
US6673511B1 (en) * | 1999-10-29 | 2004-01-06 | Shin-Etsu Chemical Co., Ltd. | Resist composition |
US7192681B2 (en) | 2001-07-05 | 2007-03-20 | Fuji Photo Film Co., Ltd. | Positive photosensitive composition |
US6645696B1 (en) * | 2001-11-30 | 2003-11-11 | Euv Llc. | Photoimageable composition |
US20040166434A1 (en) | 2003-02-21 | 2004-08-26 | Dammel Ralph R. | Photoresist composition for deep ultraviolet lithography |
JP4235466B2 (ja) * | 2003-02-24 | 2009-03-11 | Azエレクトロニックマテリアルズ株式会社 | 水溶性樹脂組成物、パターン形成方法及びレジストパターンの検査方法 |
US20060154171A1 (en) * | 2003-02-25 | 2006-07-13 | Taku Hirayama | Photoresist composition and method of forming resist pattern |
JP4012480B2 (ja) * | 2003-03-28 | 2007-11-21 | Azエレクトロニックマテリアルズ株式会社 | 微細パターン形成補助剤及びその製造法 |
JP2004334060A (ja) * | 2003-05-12 | 2004-11-25 | Shin Etsu Chem Co Ltd | 化学増幅型レジスト用光酸発生剤及びそれを含有するレジスト材料並びにパターン形成方法 |
US7189491B2 (en) * | 2003-12-11 | 2007-03-13 | Az Electronic Materials Usa Corp. | Photoresist composition for deep UV and process thereof |
US7595141B2 (en) * | 2004-10-26 | 2009-09-29 | Az Electronic Materials Usa Corp. | Composition for coating over a photoresist pattern |
US7537879B2 (en) | 2004-11-22 | 2009-05-26 | Az Electronic Materials Usa Corp. | Photoresist composition for deep UV and process thereof |
JP5203575B2 (ja) * | 2005-05-04 | 2013-06-05 | ローム・アンド・ハース・エレクトロニック・マテリアルズ,エル.エル.シー. | コーティング組成物 |
US7255970B2 (en) * | 2005-07-12 | 2007-08-14 | Az Electronic Materials Usa Corp. | Photoresist composition for imaging thick films |
US20070105040A1 (en) * | 2005-11-10 | 2007-05-10 | Toukhy Medhat A | Developable undercoating composition for thick photoresist layers |
JP4857138B2 (ja) | 2006-03-23 | 2012-01-18 | 富士フイルム株式会社 | レジスト組成物及びそれを用いたパターン形成方法 |
US7923200B2 (en) * | 2007-04-09 | 2011-04-12 | Az Electronic Materials Usa Corp. | Composition for coating over a photoresist pattern comprising a lactam |
JP5069494B2 (ja) * | 2007-05-01 | 2012-11-07 | AzエレクトロニックマテリアルズIp株式会社 | 微細化パターン形成用水溶性樹脂組成物およびこれを用いた微細パターン形成方法 |
US20090042148A1 (en) * | 2007-08-06 | 2009-02-12 | Munirathna Padmanaban | Photoresist Composition for Deep UV and Process Thereof |
JP5071658B2 (ja) * | 2008-02-14 | 2012-11-14 | 信越化学工業株式会社 | レジスト材料、レジスト保護膜材料、及びパターン形成方法 |
JP4703674B2 (ja) * | 2008-03-14 | 2011-06-15 | 富士フイルム株式会社 | レジスト組成物及びそれを用いたパターン形成方法 |
US7745077B2 (en) * | 2008-06-18 | 2010-06-29 | Az Electronic Materials Usa Corp. | Composition for coating over a photoresist pattern |
US8168367B2 (en) | 2008-07-11 | 2012-05-01 | Shin-Etsu Chemical Co., Ltd. | Resist composition and patterning process |
US20100081085A1 (en) * | 2008-09-29 | 2010-04-01 | Sumitomo Chemical Company, Limited | Polymer and Resist Composition Comprising the Same |
EP2478414B1 (en) | 2009-09-16 | 2014-12-31 | FUJIFILM Corporation | Actinic-ray- or radiation-sensitive resin composition and method of forming a pattern using the same |
US8852848B2 (en) | 2010-07-28 | 2014-10-07 | Z Electronic Materials USA Corp. | Composition for coating over a photoresist pattern |
JP5527236B2 (ja) | 2011-01-31 | 2014-06-18 | 信越化学工業株式会社 | ポジ型化学増幅レジスト材料、パターン形成方法及び酸分解性ケトエステル化合物 |
US8871425B2 (en) | 2012-02-09 | 2014-10-28 | Az Electronic Materials (Luxembourg) S.A.R.L. | Low dielectric photoimageable compositions and electronic devices made therefrom |
CN109844641B (zh) | 2016-08-09 | 2022-10-11 | 默克专利有限公司 | 环境稳定的厚膜的化学放大抗蚀剂 |
Family Cites Families (13)
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JPS63149640A (ja) | 1986-12-12 | 1988-06-22 | Konica Corp | 感光性組成物および感光性平版印刷版 |
CA2000855A1 (en) | 1988-11-17 | 1990-05-17 | Mohammad Z. Ali | Triazine photoinitiators in a ternary system for addition polymerization |
JP3010607B2 (ja) | 1992-02-25 | 2000-02-21 | ジェイエスアール株式会社 | 感放射線性樹脂組成物 |
JPH05289322A (ja) | 1992-04-10 | 1993-11-05 | Hitachi Ltd | パタン形成材料及びそれを用いたパタン形成方法 |
JP3293940B2 (ja) | 1993-03-12 | 2002-06-17 | 株式会社東芝 | 感光性組成物及びそれを用いたパターン形成方法 |
JPH0792678A (ja) | 1993-06-29 | 1995-04-07 | Nippon Zeon Co Ltd | レジスト組成物 |
JPH07120929A (ja) | 1993-09-01 | 1995-05-12 | Toshiba Corp | 感光性組成物 |
JP3297199B2 (ja) | 1993-09-14 | 2002-07-02 | 株式会社東芝 | レジスト組成物 |
JPH07128859A (ja) | 1993-11-04 | 1995-05-19 | Wako Pure Chem Ind Ltd | レジスト組成物 |
JP3203995B2 (ja) * | 1993-12-24 | 2001-09-04 | ジェイエスアール株式会社 | 感放射線性樹脂組成物 |
EP0780732B1 (en) * | 1995-12-21 | 2003-07-09 | Wako Pure Chemical Industries Ltd | Polymer composition and resist material |
TW574629B (en) * | 1997-02-28 | 2004-02-01 | Shinetsu Chemical Co | Polystyrene derivative chemically amplified positive resist compositions, and patterning method |
US6048661A (en) * | 1997-03-05 | 2000-04-11 | Shin-Etsu Chemical Co., Ltd. | Polymeric compounds, chemically amplified positive type resist materials and process for pattern formation |
-
1998
- 1998-06-25 TW TW087110416A patent/TW526390B/zh active
- 1998-06-26 KR KR1019980024358A patent/KR100539641B1/ko not_active IP Right Cessation
- 1998-06-26 US US09/105,003 patent/US6274286B1/en not_active Expired - Lifetime
- 1998-06-26 EP EP98305072A patent/EP0887705B1/en not_active Expired - Lifetime
- 1998-06-26 DE DE69807602T patent/DE69807602T2/de not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
EP0887705A1 (en) | 1998-12-30 |
DE69807602T2 (de) | 2003-06-05 |
KR100539641B1 (ko) | 2006-04-21 |
US6274286B1 (en) | 2001-08-14 |
TW526390B (en) | 2003-04-01 |
DE69807602D1 (de) | 2002-10-10 |
EP0887705B1 (en) | 2002-09-04 |
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