JP3712218B2 - 化学増幅型ホトレジスト組成物 - Google Patents
化学増幅型ホトレジスト組成物 Download PDFInfo
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- JP3712218B2 JP3712218B2 JP01158197A JP1158197A JP3712218B2 JP 3712218 B2 JP3712218 B2 JP 3712218B2 JP 01158197 A JP01158197 A JP 01158197A JP 1158197 A JP1158197 A JP 1158197A JP 3712218 B2 JP3712218 B2 JP 3712218B2
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- Prior art keywords
- acid
- group
- chemically amplified
- photoresist composition
- methacrylic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000203 mixture Substances 0.000 title claims description 20
- 229920002120 photoresistant polymer Polymers 0.000 title claims description 18
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 25
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 24
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 16
- 229920001577 copolymer Polymers 0.000 claims description 15
- 239000004925 Acrylic resin Substances 0.000 claims description 11
- 229920000178 Acrylic resin Polymers 0.000 claims description 11
- 239000003513 alkali Substances 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000000470 constituent Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- -1 acrylate ester Chemical class 0.000 description 31
- 239000000178 monomer Substances 0.000 description 18
- 238000001312 dry etching Methods 0.000 description 13
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- QHGUPRQTQITEPO-UHFFFAOYSA-N oxan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCO1 QHGUPRQTQITEPO-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
- 230000035945 sensitivity Effects 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 3
- DLDWUFCUUXXYTB-UHFFFAOYSA-N (2-oxo-1,2-diphenylethyl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 DLDWUFCUUXXYTB-UHFFFAOYSA-N 0.000 description 2
- MZVABYGYVXBZDP-UHFFFAOYSA-N 1-adamantyl 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC2CC1(OC(=O)C(=C)C)C3 MZVABYGYVXBZDP-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- XVQNGICOIZBDTJ-UHFFFAOYSA-N 3-hydroxy-3-methyloxolan-2-one Chemical compound CC1(O)CCOC1=O XVQNGICOIZBDTJ-UHFFFAOYSA-N 0.000 description 2
- VOYDEHILKLSVNN-UHFFFAOYSA-N 3-methoxy-2h-furan-5-one Chemical compound COC1=CC(=O)OC1 VOYDEHILKLSVNN-UHFFFAOYSA-N 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 2
- 125000005396 acrylic acid ester group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- VGZKCAUAQHHGDK-UHFFFAOYSA-M bis(4-tert-butylphenyl)iodanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(C(C)(C)C)=CC=C1[I+]C1=CC=C(C(C)(C)C)C=C1 VGZKCAUAQHHGDK-UHFFFAOYSA-M 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004440 column chromatography 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
- 238000005530 etching Methods 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000002887 hydroxy group Chemical class [H]O* 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229940079877 pyrogallol Drugs 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- CVBASHMCALKFME-UHFFFAOYSA-N (4-methoxyphenyl)-diphenylsulfanium Chemical compound C1=CC(OC)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 CVBASHMCALKFME-UHFFFAOYSA-N 0.000 description 1
- YXSLFXLNXREQFW-UHFFFAOYSA-M (4-methoxyphenyl)-phenyliodanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(OC)=CC=C1[I+]C1=CC=CC=C1 YXSLFXLNXREQFW-UHFFFAOYSA-M 0.000 description 1
- RLAWXWSZTKMPQQ-UHFFFAOYSA-M (4-tert-butylphenyl)-diphenylsulfanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(C(C)(C)C)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 RLAWXWSZTKMPQQ-UHFFFAOYSA-M 0.000 description 1
- NZUPFZNVGSWLQC-UHFFFAOYSA-N 1,3,5-tris(2,3-dibromopropyl)-1,3,5-triazinane-2,4,6-trione Chemical compound BrCC(Br)CN1C(=O)N(CC(Br)CBr)C(=O)N(CC(Br)CBr)C1=O NZUPFZNVGSWLQC-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LAVARTIQQDZFNT-UHFFFAOYSA-N 1-(1-methoxypropan-2-yloxy)propan-2-yl acetate Chemical compound COCC(C)OCC(C)OC(C)=O LAVARTIQQDZFNT-UHFFFAOYSA-N 0.000 description 1
- OESYNCIYSBWEQV-UHFFFAOYSA-N 1-[diazo-(2,4-dimethylphenyl)sulfonylmethyl]sulfonyl-2,4-dimethylbenzene Chemical compound CC1=CC(C)=CC=C1S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1=CC=C(C)C=C1C OESYNCIYSBWEQV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- DBZKLCIHFPDWMJ-UHFFFAOYSA-N 1-ethoxyethyl prop-2-enoate Chemical compound CCOC(C)OC(=O)C=C DBZKLCIHFPDWMJ-UHFFFAOYSA-N 0.000 description 1
- RDGGDLYJSYBBID-UHFFFAOYSA-N 1-methoxypropyl prop-2-enoate Chemical compound CCC(OC)OC(=O)C=C RDGGDLYJSYBBID-UHFFFAOYSA-N 0.000 description 1
- BVBUVHZVGAXBJX-UHFFFAOYSA-N 2,4,6-tris(2,3-dibromopropyl)-1,3,5-triazine Chemical compound BrCC(Br)CC1=NC(CC(Br)CBr)=NC(CC(Br)CBr)=N1 BVBUVHZVGAXBJX-UHFFFAOYSA-N 0.000 description 1
- BFQFFNWLTHFJOZ-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(C=2C=C3OCOC3=CC=2)=N1 BFQFFNWLTHFJOZ-UHFFFAOYSA-N 0.000 description 1
- XXXFZKQPYACQLD-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl acetate Chemical compound CC(=O)OCCOCCO XXXFZKQPYACQLD-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- ZJRNXDIVAGHETA-UHFFFAOYSA-N 2-[2-(3,4-dimethoxyphenyl)ethenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C1=C(OC)C(OC)=CC=C1C=CC1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 ZJRNXDIVAGHETA-UHFFFAOYSA-N 0.000 description 1
- XCIXLYIKKUQVST-UHFFFAOYSA-N 2-[2-(3,5-dimethoxyphenyl)ethenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound COC1=CC(OC)=CC(C=CC=2N=C(N=C(N=2)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl)=C1 XCIXLYIKKUQVST-UHFFFAOYSA-N 0.000 description 1
- XOPKKHCDIAYUSK-UHFFFAOYSA-N 2-[2-(5-methylfuran-2-yl)ethenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound O1C(C)=CC=C1C=CC1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 XOPKKHCDIAYUSK-UHFFFAOYSA-N 0.000 description 1
- SAFWZKVQMVOANB-UHFFFAOYSA-N 2-[tert-butylsulfonyl(diazo)methyl]sulfonyl-2-methylpropane Chemical compound CC(C)(C)S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C(C)(C)C SAFWZKVQMVOANB-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- GGXVWQGJAWFVRI-UHFFFAOYSA-N 2-hydroxy-1,2-diphenylpropan-1-one;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.C=1C=CC=CC=1C(O)(C)C(=O)C1=CC=CC=C1 GGXVWQGJAWFVRI-UHFFFAOYSA-N 0.000 description 1
- HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 description 1
- PPPFYBPQAPISCT-UHFFFAOYSA-N 2-hydroxypropyl acetate Chemical compound CC(O)COC(C)=O PPPFYBPQAPISCT-UHFFFAOYSA-N 0.000 description 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- GFPAFTLIWBGZMF-UHFFFAOYSA-N 3-hydroxy-4-methyloxolan-2-one Chemical compound CC1COC(=O)C1O GFPAFTLIWBGZMF-UHFFFAOYSA-N 0.000 description 1
- RUKHOZSOUYZMQQ-UHFFFAOYSA-N 4,4,6,6-tetramethylbicyclo[3.1.1]heptan-3-one Chemical group C1C2C(C)(C)C1CC(=O)C2(C)C RUKHOZSOUYZMQQ-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- SABBJFPNIAIRGR-UHFFFAOYSA-N NC(CO1)=CC1=O Chemical compound NC(CO1)=CC1=O SABBJFPNIAIRGR-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- LFJLNVUGIWJQCX-UHFFFAOYSA-N [[(4-bromophenyl)-cyanomethylidene]amino] methanesulfonate Chemical compound CS(=O)(=O)ON=C(C#N)C1=CC=C(Br)C=C1 LFJLNVUGIWJQCX-UHFFFAOYSA-N 0.000 description 1
- XDHUWCBFSRIEEC-UHFFFAOYSA-N [[cyano(phenyl)methylidene]amino] methanesulfonate Chemical compound CS(=O)(=O)ON=C(C#N)C1=CC=CC=C1 XDHUWCBFSRIEEC-UHFFFAOYSA-N 0.000 description 1
- PEJLVNJVORRJOP-UHFFFAOYSA-N [[cyano(phenyl)methylidene]amino] trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)ON=C(C#N)C1=CC=CC=C1 PEJLVNJVORRJOP-UHFFFAOYSA-N 0.000 description 1
- UPXATANHGSYTNL-UHFFFAOYSA-N [[cyano-(4-methoxyphenyl)methylidene]amino] ethanesulfonate Chemical compound CCS(=O)(=O)ON=C(C#N)C1=CC=C(OC)C=C1 UPXATANHGSYTNL-UHFFFAOYSA-N 0.000 description 1
- BADIYTSGNBSILF-UHFFFAOYSA-N [[cyano-(4-methoxyphenyl)methylidene]amino] methanesulfonate Chemical compound COC1=CC=C(C(=NOS(C)(=O)=O)C#N)C=C1 BADIYTSGNBSILF-UHFFFAOYSA-N 0.000 description 1
- ZMIGBWNVUSOGIL-UHFFFAOYSA-N [[cyano-(4-methoxyphenyl)methylidene]amino] trifluoromethanesulfonate Chemical compound COC1=CC=C(C(=NOS(=O)(=O)C(F)(F)F)C#N)C=C1 ZMIGBWNVUSOGIL-UHFFFAOYSA-N 0.000 description 1
- WVCAZSUCPKYBCC-UHFFFAOYSA-N [[cyano-(4-methylphenyl)methylidene]amino] propane-1-sulfonate Chemical compound CCCS(=O)(=O)ON=C(C#N)C1=CC=C(C)C=C1 WVCAZSUCPKYBCC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 150000001241 acetals Chemical class 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical class [*:2]C([*:1])=O 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 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 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- XAEHFYRPQZYFQS-UHFFFAOYSA-N dodecyl prop-2-enoate;2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C.CCCCCCCCCCCCOC(=O)C=C XAEHFYRPQZYFQS-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- UHKJHMOIRYZSTH-UHFFFAOYSA-N ethyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OCC UHKJHMOIRYZSTH-UHFFFAOYSA-N 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N methyl 2-hydroxypropionate Chemical group COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- YWTJTYXQYJSKNB-UHFFFAOYSA-N methyl propaneperoxoate Chemical compound CCC(=O)OOC YWTJTYXQYJSKNB-UHFFFAOYSA-N 0.000 description 1
- CWKLZLBVOJRSOM-UHFFFAOYSA-N methyl pyruvate Chemical compound COC(=O)C(C)=O CWKLZLBVOJRSOM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 229940065472 octyl acrylate Drugs 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- FGWRVVZMNXRWDQ-UHFFFAOYSA-N oxan-2-yl prop-2-enoate Chemical group C=CC(=O)OC1CCCCO1 FGWRVVZMNXRWDQ-UHFFFAOYSA-N 0.000 description 1
- FEUIEHHLVZUGPB-UHFFFAOYSA-N oxolan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC1CCCO1 FEUIEHHLVZUGPB-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- 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
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Materials For Photolithography (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP01158197A JP3712218B2 (ja) | 1997-01-24 | 1997-01-24 | 化学増幅型ホトレジスト組成物 |
| US09/562,458 US6388101B1 (en) | 1997-01-24 | 2000-05-02 | Chemical-sensitization photoresist composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP01158197A JP3712218B2 (ja) | 1997-01-24 | 1997-01-24 | 化学増幅型ホトレジスト組成物 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003207338A Division JP3719606B2 (ja) | 2003-08-12 | 2003-08-12 | 化学増幅型ホトレジスト組成物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPH10207069A JPH10207069A (ja) | 1998-08-07 |
| JPH10207069A5 JPH10207069A5 (enExample) | 2004-08-26 |
| JP3712218B2 true JP3712218B2 (ja) | 2005-11-02 |
Family
ID=11781884
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP01158197A Expired - Fee Related JP3712218B2 (ja) | 1997-01-24 | 1997-01-24 | 化学増幅型ホトレジスト組成物 |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US6388101B1 (enExample) |
| JP (1) | JP3712218B2 (enExample) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6214517B1 (en) | 1997-02-17 | 2001-04-10 | Fuji Photo Film Co., Ltd. | Positive photoresist composition |
| KR100574574B1 (ko) | 1998-08-26 | 2006-04-28 | 스미또모 가가꾸 가부시키가이샤 | 화학 증폭형 포지티브 내식막 조성물 |
| JP4131062B2 (ja) * | 1998-09-25 | 2008-08-13 | 信越化学工業株式会社 | 新規なラクトン含有化合物、高分子化合物、レジスト材料及びパターン形成方法 |
| WO2001004706A1 (en) * | 1999-07-12 | 2001-01-18 | Mitsubishi Rayon Co., Ltd. | Chemical amplification resist composition |
| US6787283B1 (en) | 1999-07-22 | 2004-09-07 | Fuji Photo Film Co., Ltd. | Positive photoresist composition for far ultraviolet exposure |
| JP2001215704A (ja) | 2000-01-31 | 2001-08-10 | Sumitomo Chem Co Ltd | 化学増幅型ポジ型レジスト組成物 |
| JP4576737B2 (ja) | 2000-06-09 | 2010-11-10 | Ｊｓｒ株式会社 | 感放射線性樹脂組成物 |
| JP4567147B2 (ja) * | 2000-06-21 | 2010-10-20 | 日本曹達株式会社 | ラクトン環を側鎖に有する（メタ）アクリル酸重合体及びその製造方法 |
| WO2002004532A1 (en) * | 2000-07-12 | 2002-01-17 | Mitsubishi Rayon Co., Ltd. | Resins for resists and chemically amplifiable resist compositions |
| US6727039B2 (en) * | 2000-09-25 | 2004-04-27 | Fuji Photo Film Co., Ltd. | Positive photoresist composition |
| JP2002116542A (ja) * | 2000-10-06 | 2002-04-19 | Daicel Chem Ind Ltd | フォトレジスト用高分子化合物及びフォトレジスト用樹脂組成物 |
| KR100832954B1 (ko) | 2000-12-13 | 2008-05-27 | 다이셀 가가꾸 고교 가부시끼가이샤 | 포토레지스트용 고분자 및 포토레지스트용 수지 조성물 |
| KR100688486B1 (ko) * | 2000-12-14 | 2007-03-09 | 삼성전자주식회사 | 프로텍팅 그룹이 있는 감광성 중합체 및 이를 포함하는포토레지스트 조성물 |
| JP4117112B2 (ja) | 2001-03-30 | 2008-07-16 | 富士フイルム株式会社 | ポジ型フォトレジスト組成物 |
| JP4255100B2 (ja) | 2001-04-06 | 2009-04-15 | 富士フイルム株式会社 | ＡｒＦエキシマレ−ザ−露光用ポジ型フォトレジスト組成物及びそれを用いたパタ−ン形成方法 |
| TWI291953B (enExample) | 2001-10-23 | 2008-01-01 | Mitsubishi Rayon Co | |
| TWI366067B (en) | 2003-09-10 | 2012-06-11 | Fujifilm Corp | Photosensitive composition and pattern forming method using the same |
| US7488565B2 (en) * | 2003-10-01 | 2009-02-10 | Chevron U.S.A. Inc. | Photoresist compositions comprising diamondoid derivatives |
| TWI375121B (en) * | 2004-06-28 | 2012-10-21 | Fujifilm Corp | Photosensitive composition and method for forming pattern using the same |
| US7960087B2 (en) | 2005-03-11 | 2011-06-14 | Fujifilm Corporation | Positive photosensitive composition and pattern-forming method using the same |
| JP4731200B2 (ja) | 2005-05-10 | 2011-07-20 | 丸善石油化学株式会社 | 半導体リソグラフィー用共重合体の製造方法 |
| JP4796792B2 (ja) * | 2005-06-28 | 2011-10-19 | 富士フイルム株式会社 | ポジ型感光性組成物及びそれを用いたパターン形成方法 |
| JP5030474B2 (ja) * | 2006-05-18 | 2012-09-19 | 丸善石油化学株式会社 | 半導体リソグラフィー用樹脂組成物 |
| JP2008106084A (ja) | 2006-10-23 | 2008-05-08 | Maruzen Petrochem Co Ltd | 半導体リソグラフィー用共重合体、組成物並びに該共重合体の製造方法 |
| JP4355011B2 (ja) | 2006-11-07 | 2009-10-28 | 丸善石油化学株式会社 | 液浸リソグラフィー用共重合体及び組成物 |
| JP5588095B2 (ja) | 2006-12-06 | 2014-09-10 | 丸善石油化学株式会社 | 半導体リソグラフィー用共重合体とその製造方法 |
| KR101446819B1 (ko) | 2006-12-22 | 2014-10-01 | 마루젠 세끼유가가꾸 가부시키가이샤 | 반도체 리소그래피용 중합체의 제조 방법 |
| JP5077355B2 (ja) * | 2007-10-01 | 2012-11-21 | Ｊｓｒ株式会社 | 感放射線性組成物 |
| JP5177374B2 (ja) * | 2007-10-12 | 2013-04-03 | 三菱レイヨン株式会社 | （メタ）アクリル酸エステルおよびその製造方法 |
| JP5806800B2 (ja) * | 2008-03-28 | 2015-11-10 | 富士フイルム株式会社 | ポジ型レジスト組成物およびそれを用いたパターン形成方法 |
| JP5427447B2 (ja) * | 2008-03-28 | 2014-02-26 | 富士フイルム株式会社 | ポジ型感光性組成物及びそれを用いたパターン形成方法 |
| JP5548406B2 (ja) | 2008-08-22 | 2014-07-16 | 東京応化工業株式会社 | ポジ型レジスト組成物、レジストパターン形成方法、高分子化合物 |
| TWI533082B (zh) | 2008-09-10 | 2016-05-11 | Jsr股份有限公司 | 敏輻射性樹脂組成物 |
| CN102150083B (zh) * | 2008-09-12 | 2013-09-04 | Jsr株式会社 | 放射线敏感性树脂组合物及抗蚀剂图案形成方法 |
| JP5591465B2 (ja) | 2008-10-30 | 2014-09-17 | 丸善石油化学株式会社 | 濃度が均一な半導体リソグラフィー用共重合体溶液の製造方法 |
| JP5232663B2 (ja) | 2009-01-14 | 2013-07-10 | 東京応化工業株式会社 | レジスト組成物、レジストパターン形成方法、高分子化合物及び化合物 |
| JP5264575B2 (ja) | 2009-03-11 | 2013-08-14 | 東京応化工業株式会社 | ポジ型レジスト組成物およびレジストパターン形成方法 |
| JP5481979B2 (ja) * | 2009-07-15 | 2014-04-23 | Ｊｓｒ株式会社 | 感放射線性樹脂組成物及びそれに用いられる重合体 |
| JP5812006B2 (ja) | 2010-09-29 | 2015-11-11 | Jsr株式会社 | 感放射線性樹脂組成物及びパターン形成方法 |
| JP6002378B2 (ja) | 2011-11-24 | 2016-10-05 | 東京応化工業株式会社 | 高分子化合物の製造方法 |
| US8795948B2 (en) | 2012-03-22 | 2014-08-05 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition, method of forming resist pattern and polymeric compound |
| US8795947B2 (en) | 2012-03-22 | 2014-08-05 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition and method of forming resist pattern |
| JP5772760B2 (ja) | 2012-08-13 | 2015-09-02 | 信越化学工業株式会社 | ポジ型レジスト材料並びにこれを用いたパターン形成方法 |
| JP5573924B2 (ja) * | 2012-11-09 | 2014-08-20 | 三菱レイヨン株式会社 | （メタ）アクリル酸エステルおよびその製造方法 |
| WO2014148241A1 (ja) | 2013-03-22 | 2014-09-25 | Jsr株式会社 | 感放射線性樹脂組成物、レジストパターン形成方法、重合体及び化合物の製造方法 |
| JP6323460B2 (ja) | 2013-09-26 | 2018-05-16 | 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 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4276218A (en) * | 1979-08-16 | 1981-06-30 | Bayer Aktiengesellschaft | Preparation of dihalogenovinyl-γ-butyrolactones |
| JPS57141644A (en) | 1981-02-26 | 1982-09-02 | Konishiroku Photo Ind Co Ltd | Photographic element |
| US4882434A (en) * | 1986-10-29 | 1989-11-21 | Takeda Chemical Industries, Ltd. | Gamma-lactonecarboxylic acid derivatives and their use as antibacterial agents or intermediates |
| JP2881969B2 (ja) | 1990-06-05 | 1999-04-12 | 富士通株式会社 | 放射線感光レジストとパターン形成方法 |
| JPH05265212A (ja) | 1992-03-17 | 1993-10-15 | Fujitsu Ltd | レジスト材料およびそれを用いるパターン形成方法 |
| JP3236073B2 (ja) | 1992-06-16 | 2001-12-04 | 富士通株式会社 | レジスト組成物及びそれを用いたパターン形成方法 |
| JP3009320B2 (ja) | 1993-12-24 | 2000-02-14 | 三菱電機株式会社 | 分解性樹脂および感光性樹脂組成物 |
| JP3297272B2 (ja) | 1995-07-14 | 2002-07-02 | 富士通株式会社 | レジスト組成物及びレジストパターンの形成方法 |
-
1997
- 1997-01-24 JP JP01158197A patent/JP3712218B2/ja not_active Expired - Fee Related
-
2000
- 2000-05-02 US US09/562,458 patent/US6388101B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH10207069A (ja) | 1998-08-07 |
| US6388101B1 (en) | 2002-05-14 |
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