KR100778635B1 - 염기성 화합물, 레지스트 재료 및 패턴 형성 방법 - Google Patents
염기성 화합물, 레지스트 재료 및 패턴 형성 방법 Download PDFInfo
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- KR100778635B1 KR100778635B1 KR1020040035956A KR20040035956A KR100778635B1 KR 100778635 B1 KR100778635 B1 KR 100778635B1 KR 1020040035956 A KR1020040035956 A KR 1020040035956A KR 20040035956 A KR20040035956 A KR 20040035956A KR 100778635 B1 KR100778635 B1 KR 100778635B1
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- 150000007514 bases Chemical class 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title claims description 25
- 230000008569 process Effects 0.000 title claims description 5
- 239000000203 mixture Substances 0.000 title description 12
- 238000000059 patterning Methods 0.000 title 1
- 125000006165 cyclic alkyl group Chemical group 0.000 claims abstract description 44
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 41
- 239000000463 material Substances 0.000 claims abstract description 41
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 34
- 125000000524 functional group Chemical group 0.000 claims abstract description 31
- 125000001033 ether group Chemical group 0.000 claims abstract description 30
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 28
- 125000004036 acetal group Chemical group 0.000 claims abstract description 27
- 125000004185 ester group Chemical group 0.000 claims abstract description 26
- 125000000101 thioether group Chemical group 0.000 claims abstract description 23
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 22
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 22
- 125000005587 carbonate group Chemical group 0.000 claims abstract description 17
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims abstract description 15
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims abstract description 11
- 238000010894 electron beam technology Methods 0.000 claims abstract description 6
- -1 cyclic acetals Chemical class 0.000 claims description 352
- 125000004432 carbon atom Chemical group C* 0.000 claims description 81
- 239000002253 acid Substances 0.000 claims description 50
- 125000002947 alkylene group Chemical group 0.000 claims description 24
- 239000002585 base Substances 0.000 claims description 24
- 229920005989 resin Polymers 0.000 claims description 20
- 239000011347 resin Substances 0.000 claims description 20
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
- 239000000758 substrate Substances 0.000 claims description 13
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 239000003431 cross linking reagent Substances 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 150000005676 cyclic carbonates Chemical class 0.000 claims description 7
- 238000004090 dissolution Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 238000004132 cross linking Methods 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 230000000694 effects Effects 0.000 abstract description 10
- 238000013329 compounding Methods 0.000 abstract description 8
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 238000002156 mixing Methods 0.000 abstract description 2
- 150000001412 amines Chemical class 0.000 description 46
- 230000015572 biosynthetic process Effects 0.000 description 33
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 33
- 238000003786 synthesis reaction Methods 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
- 239000007983 Tris buffer Substances 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 22
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- KZJRKRQSDZGHEC-UHFFFAOYSA-N 2,2,2-trifluoro-1-phenylethanone Chemical compound FC(F)(F)C(=O)C1=CC=CC=C1 KZJRKRQSDZGHEC-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- 0 C*(*[n]1c2ccccc2nc1*)S Chemical compound C*(*[n]1c2ccccc2nc1*)S 0.000 description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 150000002430 hydrocarbons Chemical group 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- WNXNUPJZWYOKMW-UHFFFAOYSA-M 5-bromopentanoate Chemical compound [O-]C(=O)CCCCBr WNXNUPJZWYOKMW-UHFFFAOYSA-M 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 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 7
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- 229940017219 methyl propionate Drugs 0.000 description 7
- 125000001624 naphthyl group Chemical group 0.000 description 7
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- NCJZVRPXSSYDBG-UHFFFAOYSA-N 2,2,2-trifluoro-1-(4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(=O)C(F)(F)F)C=C1 NCJZVRPXSSYDBG-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- KYXIHKXHBSORRJ-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)-2,2,2-trifluoroethanone Chemical compound CC1=CC=C(C(=O)C(F)(F)F)C(C)=C1 KYXIHKXHBSORRJ-UHFFFAOYSA-N 0.000 description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 5
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 5
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 5
- 125000004864 4-thiomethylphenyl group Chemical group 0.000 description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
- 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 5
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 5
- 238000010626 work up procedure Methods 0.000 description 5
- LJHFIVQEAFAURQ-ZPUQHVIOSA-N (NE)-N-[(2E)-2-hydroxyiminoethylidene]hydroxylamine Chemical class O\N=C\C=N\O LJHFIVQEAFAURQ-ZPUQHVIOSA-N 0.000 description 4
- VINRTVDNUHIWCB-UHFFFAOYSA-N 2,2,2-trifluoro-1-(2,4,6-trimethylphenyl)ethanone Chemical compound CC1=CC(C)=C(C(=O)C(F)(F)F)C(C)=C1 VINRTVDNUHIWCB-UHFFFAOYSA-N 0.000 description 4
- DYILUJUELMWXAL-UHFFFAOYSA-N 2,2,2-trifluoro-1-(4-methylphenyl)ethanone Chemical compound CC1=CC=C(C(=O)C(F)(F)F)C=C1 DYILUJUELMWXAL-UHFFFAOYSA-N 0.000 description 4
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical class C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 4
- 125000000732 arylene group Chemical group 0.000 description 4
- 229920005601 base polymer Polymers 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 4
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 4
- 230000007261 regionalization Effects 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 4
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- JHQDBQYFKARISA-UHFFFAOYSA-N 2,2,2-trifluoro-1-(2-methylphenyl)ethanone Chemical compound CC1=CC=CC=C1C(=O)C(F)(F)F JHQDBQYFKARISA-UHFFFAOYSA-N 0.000 description 3
- DJRLXHBFATVHJX-UHFFFAOYSA-N 2-(benzimidazol-1-yl)ethanol Chemical compound C1=CC=C2N(CCO)C=NC2=C1 DJRLXHBFATVHJX-UHFFFAOYSA-N 0.000 description 3
- KJXSTIJHXKFZKV-UHFFFAOYSA-N 2-(cyclohexylmethylsulfanyl)cyclohexan-1-one;trifluoromethanesulfonic acid Chemical compound [O-]S(=O)(=O)C(F)(F)F.O=C1CCCCC1[SH+]CC1CCCCC1 KJXSTIJHXKFZKV-UHFFFAOYSA-N 0.000 description 3
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- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- XULQYKHYHOXCJI-UHFFFAOYSA-N tert-butyl 2-piperidin-1-ylethyl carbonate Chemical compound CC(C)(C)OC(=O)OCCN1CCCCC1 XULQYKHYHOXCJI-UHFFFAOYSA-N 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
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 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
- 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 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 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
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 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
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
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- B60Q1/00—Arrangement of optical signalling or lighting devices, the mounting or supporting thereof or circuits therefor
- B60Q1/26—Arrangement of optical signalling or lighting devices, the mounting or supporting thereof or circuits therefor the devices being primarily intended to indicate the vehicle, or parts thereof, or to give signals, to other traffic
- B60Q1/34—Arrangement of optical signalling or lighting devices, the mounting or supporting thereof or circuits therefor the devices being primarily intended to indicate the vehicle, or parts thereof, or to give signals, to other traffic for indicating change of drive direction
- B60Q1/343—Manually actuated switching arrangements therefor
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60Q—ARRANGEMENT OF SIGNALLING OR LIGHTING DEVICES, THE MOUNTING OR SUPPORTING THEREOF OR CIRCUITS THEREFOR, FOR VEHICLES IN GENERAL
- B60Q1/00—Arrangement of optical signalling or lighting devices, the mounting or supporting thereof or circuits therefor
- B60Q1/26—Arrangement of optical signalling or lighting devices, the mounting or supporting thereof or circuits therefor the devices being primarily intended to indicate the vehicle, or parts thereof, or to give signals, to other traffic
- B60Q1/32—Arrangement of optical signalling or lighting devices, the mounting or supporting thereof or circuits therefor the devices being primarily intended to indicate the vehicle, or parts thereof, or to give signals, to other traffic for indicating vehicle sides, e.g. clearance lights
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60Q—ARRANGEMENT OF SIGNALLING OR LIGHTING DEVICES, THE MOUNTING OR SUPPORTING THEREOF OR CIRCUITS THEREFOR, FOR VEHICLES IN GENERAL
- B60Q1/00—Arrangement of optical signalling or lighting devices, the mounting or supporting thereof or circuits therefor
- B60Q1/26—Arrangement of optical signalling or lighting devices, the mounting or supporting thereof or circuits therefor the devices being primarily intended to indicate the vehicle, or parts thereof, or to give signals, to other traffic
- B60Q1/44—Arrangement of optical signalling or lighting devices, the mounting or supporting thereof or circuits therefor the devices being primarily intended to indicate the vehicle, or parts thereof, or to give signals, to other traffic for indicating braking action or preparation for braking, e.g. by detection of the foot approaching the brake pedal
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
-
- 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
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- 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
- Y10S362/00—Illumination
- Y10S362/80—Light emitting diode
-
- 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
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- 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
- Y10S430/111—Polymer of unsaturated acid or ester
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Materials For Photolithography (AREA)
- Plural Heterocyclic Compounds (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Abstract
Description
Claims (12)
- 하기 화학식 1로 표시되는 벤즈이미다졸 골격 및 극성 관능기를 갖는 염기성 화합물 중 1종 또는 2종 이상을 함유하는 것을 특징으로 하는 레지스트 재료.<화학식 1>식 중, R1은 수소 원자, 탄소수 1 내지 10의 직쇄상, 분지상 또는 환상 알킬기, 탄소수 6 내지 10의 아릴기 또는 탄소수 7 내지 10의 아랄킬기이고, R2는 탄소수 1 내지 20의 직쇄상, 분지상 또는 환상의 극성 관능기를 갖는 알킬기이고, 극성 관능기로서 에스테르기, 아세탈기 또는 시아노기를 하나 이상 포함하고, 그 밖에 수산기, 카르보닐기, 에테르기, 술피드기 또는 카르보네이트기를 하나 이상 포함할 수도 있다.
- 하기 화학식 2 내지 7로 표시되는 벤즈이미다졸 골격 및 극성 관능기를 갖는 염기성 화합물 중 1종 또는 2종 이상을 함유하는 것을 특징으로 하는 레지스트 재료.<화학식 2><화학식 3><화학식 4><화학식 5><화학식 6><화학식 7>식 중, R1은 수소 원자, 탄소수 1 내지 10의 직쇄상, 분지상 또는 환상 알킬기, 탄소수 6 내지 10의 아릴기 또는 탄소수 7 내지 10의 아랄킬기이고, R3, R5, R9, R12, R14는 탄소수 1 내지 10의 직쇄상, 분지상 또는 환상 알킬렌기이고, R4는 수소 원자 또는 탄소수 1 내지 15의 알킬기이고, 수산기, 카르보닐기, 에스테르기, 에테르기, 술피드기, 카르보네이트기, 시아노기 또는 아세탈기를 1개 또는 복수개 포함할 수도 있고, R6은 탄소수 1 내지 15의 알킬기이고, 수산기, 카르보닐기, 에스테르기, 에테르기, 술피드기, 카르보네이트기, 시아노기 또는 아세탈기를 1개 또는 복수개 포함할 수도 있고, R7은 탄소수 2 내지 10의 직쇄상, 분지상 또는 환상의 3가의 탄화수소기이고, R8은 각각 동일하거나 상이할 수도 있는 탄소수 1 내지 10의 아실기로서, 에스테르기 또는 에테르기를 1개 또는 복수개 포함할 수도 있거나, 또는 2개의 R8끼리 결합하여 환상 카르보네이트 또는 환상 아세탈을 형성하고, R10은 수소 원자 또는 탄소수 1 내지 10의 직쇄상, 분지상 또는 환상 알킬기이고, R11은 탄소수 1 내지 10의 직쇄상, 분지상 또는 환상 알킬기로서, 에테르기, 술피드기 또 는 아세탈기를 1개 또는 복수개 포함할 수도 있거나, 또는 R10과 R11이 결합하여 환을 형성할 수도 있고, R13은 탄소수 1 내지 10의 직쇄상, 분지상 또는 환상 알킬기이고, R13끼리 결합하여 환을 형성할 수도 있다.
- (A) 제1항 또는 제2항에 기재된 염기성 화합물,(B) 유기 용제,(C) 산불안정기로 보호된 산성 관능기를 갖는 알칼리 불용성 또는 난용성의 수지로서, 상기 산불안정기가 이탈하였을 때에 알칼리 가용성이 되는 기재 수지, 및(D) 산 발생제를 함유하는 것을 특징으로 하는 포지티브형 레지스트 재료.
- 제3항에 있어서, (E) 용해 저지제를 더 함유하는 것을 특징으로 하는 포지티브형 레지스트 재료.
- (A) 제1항 또는 제2항에 기재된 염기성 화합물,(B) 유기 용제,(C') 알칼리 가용성 수지로서, 가교제에 의한 가교에 의해서 알칼리 난용성이 되는 기재 수지,(D) 산 발생제, 및(F) 산에 의해서 가교하는 가교제를 함유하는 것을 특징으로 하는 네가티브형 레지스트 재료.
- (1) 제3항에 기재된 포지티브형 레지스트 재료를 기판 상에 도포하는 공정과,(2) 계속해서 가열 처리 후, 포토마스크를 통해 파장 300 nm 이하의 고에너지선 또는 전자선으로 노광하는 공정과,(3) 가열 처리한 후, 현상액을 이용하여 현상하는 공정을 포함하는 것을 특징으로 하는 패턴 형성 방법.
- 하기 화학식 5로 표시되는 염기성 화합물.<화학식 5>식 중, R1은 수소 원자, 탄소수 1 내지 10의 직쇄상, 분지상 또는 환상 알킬기, 탄소수 6 내지 10의 아릴기 또는 탄소수 7 내지 10의 아랄킬기이고, R9는 탄소수 1 내지 10의 직쇄상, 분지상 또는 환상의 알킬렌기이고, R10은 수소 원자 또는 탄소수 1 내지 10의 직쇄상, 분지상 또는 환상 알킬기이고, R11은 탄소수 1 내지 10의 직쇄상, 분지상 또는 환상 알킬기로서, 에테르기, 술피드기 또는 아세탈기를 1 개 또는 복수개 포함할 수도 있거나, 또는 R10과 R11이 결합하여 환을 형성할 수도 있다.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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JP2003142853A JP4009852B2 (ja) | 2003-05-21 | 2003-05-21 | 塩基性化合物、レジスト材料及びパターン形成方法 |
JPJP-P-2003-00142853 | 2003-05-21 |
Publications (2)
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KR20040101019A KR20040101019A (ko) | 2004-12-02 |
KR100778635B1 true KR100778635B1 (ko) | 2007-11-27 |
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KR1020040035956A KR100778635B1 (ko) | 2003-05-21 | 2004-05-20 | 염기성 화합물, 레지스트 재료 및 패턴 형성 방법 |
Country Status (4)
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US (1) | US7141352B2 (ko) |
JP (1) | JP4009852B2 (ko) |
KR (1) | KR100778635B1 (ko) |
TW (1) | TWI308994B (ko) |
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JP4029288B2 (ja) * | 2003-05-21 | 2008-01-09 | 信越化学工業株式会社 | レジスト材料及びパターン形成方法 |
JP4420226B2 (ja) | 2005-02-18 | 2010-02-24 | 信越化学工業株式会社 | 化学増幅ポジ型レジスト材料及びパターン形成方法 |
JP4590325B2 (ja) * | 2005-08-01 | 2010-12-01 | 富士フイルム株式会社 | レジスト組成物及び該レジスト組成物を用いたパターン形成方法 |
EP1780199B1 (en) * | 2005-10-31 | 2012-02-01 | Shin-Etsu Chemical Co., Ltd. | Novel fluorohydroxyalkyl sulfonate salts and derivatives, photoacid generators, resist compositions, and patterning process |
EP1780198B1 (en) | 2005-10-31 | 2011-10-05 | Shin-Etsu Chemical Co., Ltd. | Novel fluorosulfonyloxyalkyl sulfonate salts and derivatives, photoacid generators, resist compositions, and patterning process |
JP4803377B2 (ja) * | 2006-10-25 | 2011-10-26 | 信越化学工業株式会社 | レジスト材料及びパターン形成方法 |
TW201106101A (en) * | 2009-06-01 | 2011-02-16 | Fujifilm Electronic Materials | Chemically amplified positive photoresist composition |
JP5900340B2 (ja) * | 2010-09-17 | 2016-04-06 | Jsr株式会社 | 感放射線性樹脂組成物及びレジストパターン形成方法 |
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 |
JP5229337B2 (ja) * | 2011-02-14 | 2013-07-03 | 信越化学工業株式会社 | 含窒素有機化合物 |
JP5789623B2 (ja) | 2012-03-29 | 2015-10-07 | 富士フイルム株式会社 | 感活性光線性又は感放射線性樹脂組成物、並びにそれを用いた感活性光線性又は感放射線性膜及びパターン形成方法 |
WO2016035497A1 (ja) * | 2014-09-02 | 2016-03-10 | 富士フイルム株式会社 | パターン形成方法、電子デバイスの製造方法及び電子デバイス |
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- 2004-05-20 TW TW093114306A patent/TWI308994B/zh not_active IP Right Cessation
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TWI308994B (en) | 2009-04-21 |
TW200502695A (en) | 2005-01-16 |
JP4009852B2 (ja) | 2007-11-21 |
JP2004347738A (ja) | 2004-12-09 |
KR20040101019A (ko) | 2004-12-02 |
US7141352B2 (en) | 2006-11-28 |
US20050008968A1 (en) | 2005-01-13 |
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