JP3851476B2 - 有機反射防止重合体およびその製造方法 - Google Patents
有機反射防止重合体およびその製造方法 Download PDFInfo
- Publication number
- JP3851476B2 JP3851476B2 JP35449399A JP35449399A JP3851476B2 JP 3851476 B2 JP3851476 B2 JP 3851476B2 JP 35449399 A JP35449399 A JP 35449399A JP 35449399 A JP35449399 A JP 35449399A JP 3851476 B2 JP3851476 B2 JP 3851476B2
- Authority
- JP
- Japan
- Prior art keywords
- anthracene
- formula
- derivative
- composition
- iii
- 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.)
- Expired - Fee Related
Links
- 229920000642 polymer Polymers 0.000 title claims description 47
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 37
- -1 hydroxy, methoxycarbonyl Chemical group 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 21
- 239000006117 anti-reflective coating Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 150000001454 anthracenes Chemical class 0.000 claims description 10
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 8
- 150000001983 dialkylethers Chemical class 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- JCJNNHDZTLRSGN-UHFFFAOYSA-N anthracen-9-ylmethanol Chemical compound C1=CC=C2C(CO)=C(C=CC=C3)C3=CC2=C1 JCJNNHDZTLRSGN-UHFFFAOYSA-N 0.000 claims description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 230000003667 anti-reflective effect Effects 0.000 claims description 5
- 239000004065 semiconductor Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 4
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 claims description 3
- ASDLSKCKYGVMAI-UHFFFAOYSA-N 9,10-dioxoanthracene-2-carboxylic acid Chemical compound C1=CC=C2C(=O)C3=CC(C(=O)O)=CC=C3C(=O)C2=C1 ASDLSKCKYGVMAI-UHFFFAOYSA-N 0.000 claims 8
- XGWFJBFNAQHLEF-UHFFFAOYSA-N 9-anthroic acid Chemical compound C1=CC=C2C(C(=O)O)=C(C=CC=C3)C3=CC2=C1 XGWFJBFNAQHLEF-UHFFFAOYSA-N 0.000 claims 8
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims 4
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical compound C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 claims 4
- CCFAKBRKTKVJPO-UHFFFAOYSA-N 1-anthroic acid Chemical class C1=CC=C2C=C3C(C(=O)O)=CC=CC3=CC2=C1 CCFAKBRKTKVJPO-UHFFFAOYSA-N 0.000 claims 4
- YVXRKDVOSYFSPJ-UHFFFAOYSA-N 2-amino-7-methyl-5-oxochromeno[2,3-b]pyridine-3-carbonitrile Chemical compound NC1=C(C#N)C=C2C(=O)C3=CC(C)=CC=C3OC2=N1 YVXRKDVOSYFSPJ-UHFFFAOYSA-N 0.000 claims 4
- AUKRYONWZHRJRE-UHFFFAOYSA-N 9-anthrol Chemical compound C1=CC=C2C(O)=C(C=CC=C3)C3=CC2=C1 AUKRYONWZHRJRE-UHFFFAOYSA-N 0.000 claims 4
- YMNKUHIVVMFOFO-UHFFFAOYSA-N anthracene-9-carbaldehyde Chemical compound C1=CC=C2C(C=O)=C(C=CC=C3)C3=CC2=C1 YMNKUHIVVMFOFO-UHFFFAOYSA-N 0.000 claims 4
- KEQZHLAEKAVZLY-UHFFFAOYSA-N anthracene-9-carbonitrile Chemical compound C1=CC=C2C(C#N)=C(C=CC=C3)C3=CC2=C1 KEQZHLAEKAVZLY-UHFFFAOYSA-N 0.000 claims 4
- APAJFZPFBHMFQR-UHFFFAOYSA-N anthraflavic acid Chemical compound OC1=CC=C2C(=O)C3=CC(O)=CC=C3C(=O)C2=C1 APAJFZPFBHMFQR-UHFFFAOYSA-N 0.000 claims 4
- NUZWLKWWNNJHPT-UHFFFAOYSA-N anthralin Chemical compound C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O NUZWLKWWNNJHPT-UHFFFAOYSA-N 0.000 claims 4
- JPICKYUTICNNNJ-UHFFFAOYSA-N anthrarufin Chemical compound O=C1C2=C(O)C=CC=C2C(=O)C2=C1C=CC=C2O JPICKYUTICNNNJ-UHFFFAOYSA-N 0.000 claims 4
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 229960002311 dithranol Drugs 0.000 claims 4
- HLGMTCSSRBPNOQ-MHWRWJLKSA-N (ne)-n-(anthracen-9-ylmethylidene)hydroxylamine Chemical compound C1=CC=C2C(/C=N/O)=C(C=CC=C3)C3=CC2=C1 HLGMTCSSRBPNOQ-MHWRWJLKSA-N 0.000 claims 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 82
- 239000010408 film Substances 0.000 description 41
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 41
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- 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 32
- 238000006243 chemical reaction Methods 0.000 description 31
- 239000002904 solvent Substances 0.000 description 29
- 239000000178 monomer Substances 0.000 description 27
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 26
- 239000011347 resin Substances 0.000 description 26
- 229920005989 resin Polymers 0.000 description 26
- 230000015572 biosynthetic process Effects 0.000 description 25
- 239000000126 substance Substances 0.000 description 25
- 238000003786 synthesis reaction Methods 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000012299 nitrogen atmosphere Substances 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- MJYSISMEPNOHEG-UHFFFAOYSA-N anthracen-9-ylmethyl 2-methylprop-2-enoate Chemical compound C1=CC=C2C(COC(=O)C(=C)C)=C(C=CC=C3)C3=CC2=C1 MJYSISMEPNOHEG-UHFFFAOYSA-N 0.000 description 12
- 229920001577 copolymer Polymers 0.000 description 12
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 8
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 8
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 8
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000005530 etching Methods 0.000 description 8
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 8
- NBKFKDJHUNQQKY-UHFFFAOYSA-N (4-formylphenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=C(C=O)C=C1 NBKFKDJHUNQQKY-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229920002120 photoresistant polymer Polymers 0.000 description 6
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 6
- 229920001897 terpolymer Polymers 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 230000007261 regionalization Effects 0.000 description 5
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000001459 lithography Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- QPQYEWCOENRVAM-UHFFFAOYSA-N OCCC(C(=O)O)=C.C(C=C)(=O)OCC Chemical compound OCCC(C(=O)O)=C.C(C=C)(=O)OCC QPQYEWCOENRVAM-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- VFLDPWHFBUODDF-FCXRPNKRSA-N curcumin Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-FCXRPNKRSA-N 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000010884 ion-beam technique Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- NIBFJPXGNVPNHK-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-4-carbaldehyde Chemical group C1=CC(C=O)=C2OC(F)(F)OC2=C1 NIBFJPXGNVPNHK-UHFFFAOYSA-N 0.000 description 1
- KLNMQYHQWUWCPG-UHFFFAOYSA-N 2-anthracen-9-ylethanol Chemical compound C1=CC=C2C(CCO)=C(C=CC=C3)C3=CC2=C1 KLNMQYHQWUWCPG-UHFFFAOYSA-N 0.000 description 1
- BPTKLSBRRJFNHJ-UHFFFAOYSA-N 4-phenyldiazenylbenzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1N=NC1=CC=CC=C1 BPTKLSBRRJFNHJ-UHFFFAOYSA-N 0.000 description 1
- IFTJXHRRFDACTJ-UHFFFAOYSA-N 5-hydroxy-2-methylidenepentanoic acid methyl 2-methylprop-2-enoate Chemical compound COC(=O)C(C)=C.OCCCC(=C)C(O)=O IFTJXHRRFDACTJ-UHFFFAOYSA-N 0.000 description 1
- JMKQXTOGJDFAPJ-UHFFFAOYSA-N 5-hydroxy-2-methylidenepentanoic acid methyl prop-2-enoate Chemical compound COC(=O)C=C.OCCCC(=C)C(O)=O JMKQXTOGJDFAPJ-UHFFFAOYSA-N 0.000 description 1
- RAFGELQLHMBRHD-VFYVRILKSA-N Bixin Natural products COC(=O)C=CC(=C/C=C/C(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C(=O)O)/C)C RAFGELQLHMBRHD-VFYVRILKSA-N 0.000 description 1
- OWEKOVJMTXNOFS-UPRRUGRUSA-N CCC(C(C)(C)CC(C)(C)C(C(C=O)O)C(C)(C)CC(C)(C)C(C)[C@H](O)OCc1c(cccc2)c2cc2c1cccc2)C(OC(O)I)=O Chemical compound CCC(C(C)(C)CC(C)(C)C(C(C=O)O)C(C)(C)CC(C)(C)C(C)[C@H](O)OCc1c(cccc2)c2cc2c1cccc2)C(OC(O)I)=O OWEKOVJMTXNOFS-UPRRUGRUSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- RAFGELQLHMBRHD-UHFFFAOYSA-N alpha-Fuc-(1-2)-beta-Gal-(1-3)-(beta-GlcNAc-(1-6))-GalNAc-ol Natural products COC(=O)C=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC(O)=O RAFGELQLHMBRHD-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910003481 amorphous carbon Inorganic materials 0.000 description 1
- 239000001670 anatto Substances 0.000 description 1
- 235000012665 annatto Nutrition 0.000 description 1
- RAFGELQLHMBRHD-SLEZCNMESA-N bixin Chemical compound COC(=O)\C=C\C(\C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C(O)=O RAFGELQLHMBRHD-SLEZCNMESA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004148 curcumin Substances 0.000 description 1
- 235000012754 curcumin Nutrition 0.000 description 1
- 229940109262 curcumin Drugs 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- VFLDPWHFBUODDF-UHFFFAOYSA-N diferuloylmethane Natural products C1=C(O)C(OC)=CC(C=CC(=O)CC(=O)C=CC=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 229920005575 poly(amic acid) Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- MLVYOYVMOZFHIU-UHFFFAOYSA-M sodium;4-[(4-anilinophenyl)diazenyl]benzenesulfonate Chemical compound [Na+].C1=CC(S(=O)(=O)[O-])=CC=C1N=NC(C=C1)=CC=C1NC1=CC=CC=C1 MLVYOYVMOZFHIU-UHFFFAOYSA-M 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
- C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F20/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/017—Esters of hydroxy compounds having the esterified hydroxy group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR14763/1999 | 1999-04-23 | ||
| KR10-1999-0014763A KR100395904B1 (ko) | 1999-04-23 | 1999-04-23 | 유기 반사방지 중합체 및 그의 제조방법 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2001098024A JP2001098024A (ja) | 2001-04-10 |
| JP3851476B2 true JP3851476B2 (ja) | 2006-11-29 |
Family
ID=19582078
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP35449399A Expired - Fee Related JP3851476B2 (ja) | 1999-04-23 | 1999-12-14 | 有機反射防止重合体およびその製造方法 |
Country Status (10)
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6528235B2 (en) | 1991-11-15 | 2003-03-04 | Shipley Company, L.L.C. | Antihalation compositions |
| US6773864B1 (en) * | 1991-11-15 | 2004-08-10 | Shipley Company, L.L.C. | Antihalation compositions |
| US6472128B2 (en) * | 1996-04-30 | 2002-10-29 | Shipley Company, L.L.C. | Antihalation compositions |
| US6165697A (en) * | 1991-11-15 | 2000-12-26 | Shipley Company, L.L.C. | Antihalation compositions |
| KR100465864B1 (ko) * | 1999-03-15 | 2005-01-24 | 주식회사 하이닉스반도체 | 유기 난반사방지 중합체 및 그의 제조방법 |
| US6890448B2 (en) * | 1999-06-11 | 2005-05-10 | Shipley Company, L.L.C. | Antireflective hard mask compositions |
| KR100310252B1 (ko) * | 1999-06-22 | 2001-11-14 | 박종섭 | 유기 반사방지 중합체 및 그의 제조방법 |
| KR100427440B1 (ko) * | 1999-12-23 | 2004-04-17 | 주식회사 하이닉스반도체 | 유기 반사방지 화합물 및 그의 제조방법 |
| KR100355604B1 (ko) * | 1999-12-23 | 2002-10-12 | 주식회사 하이닉스반도체 | 난반사 방지막용 중합체와 그 제조방법 |
| KR100549574B1 (ko) * | 1999-12-30 | 2006-02-08 | 주식회사 하이닉스반도체 | 유기 반사 방지막용 중합체 및 그의 제조방법 |
| US6686124B1 (en) * | 2000-03-14 | 2004-02-03 | International Business Machines Corporation | Multifunctional polymeric materials and use thereof |
| KR100687851B1 (ko) * | 2000-06-30 | 2007-02-27 | 주식회사 하이닉스반도체 | 유기반사방지막 조성물 및 그의 제조방법 |
| KR100721181B1 (ko) * | 2000-06-30 | 2007-05-23 | 주식회사 하이닉스반도체 | 유기반사방지막 조성물 및 그의 제조방법 |
| KR100687850B1 (ko) * | 2000-06-30 | 2007-02-27 | 주식회사 하이닉스반도체 | 유기반사방지막 조성물 및 그의 제조방법 |
| KR100721182B1 (ko) * | 2000-06-30 | 2007-05-23 | 주식회사 하이닉스반도체 | 유기반사방지막 조성물 및 그의 제조방법 |
| KR100574486B1 (ko) * | 2000-06-30 | 2006-04-27 | 주식회사 하이닉스반도체 | 유기반사방지막 조성물 및 그의 제조방법 |
| TW576949B (en) | 2000-08-17 | 2004-02-21 | Shipley Co Llc | Antireflective coatings with increased etch rates |
| KR100734249B1 (ko) * | 2000-09-07 | 2007-07-02 | 삼성전자주식회사 | 축합환의 방향족 환을 포함하는 보호기를 가지는 감광성폴리머 및 이를 포함하는 레지스트 조성물 |
| US6605394B2 (en) | 2001-05-03 | 2003-08-12 | Applied Materials, Inc. | Organic bottom antireflective coating for high performance mask making using optical imaging |
| KR20020090489A (ko) * | 2001-05-28 | 2002-12-05 | 금호석유화학 주식회사 | 화학증폭형 레지스트용 중합체 및 이를 함유한 화학증폭형레지스트 조성물 |
| KR100351459B1 (ko) * | 2001-05-30 | 2002-09-05 | 주식회사 하이닉스반도체 | 유기 반사방지 중합체 및 그의 제조방법 |
| KR100351458B1 (ko) * | 2001-05-30 | 2002-09-05 | 주식회사 하이닉스반도체 | 유기 반사방지 중합체 및 그의 제조방법 |
| US6703169B2 (en) | 2001-07-23 | 2004-03-09 | Applied Materials, Inc. | Method of preparing optically imaged high performance photomasks |
| JP2004206082A (ja) * | 2002-11-20 | 2004-07-22 | Rohm & Haas Electronic Materials Llc | 多層フォトレジスト系 |
| EP1422566A1 (en) * | 2002-11-20 | 2004-05-26 | Shipley Company, L.L.C. | Multilayer photoresist systems |
| US7361447B2 (en) | 2003-07-30 | 2008-04-22 | Hynix Semiconductor Inc. | Photoresist polymer and photoresist composition containing the same |
| KR100636938B1 (ko) * | 2003-09-29 | 2006-10-19 | 주식회사 하이닉스반도체 | 포토레지스트 조성물 |
| JP2005314453A (ja) * | 2004-04-27 | 2005-11-10 | Sumitomo Chemical Co Ltd | アクリル樹脂及び該樹脂を含有する粘着剤 |
| KR101156973B1 (ko) * | 2005-03-02 | 2012-06-20 | 주식회사 동진쎄미켐 | 유기 반사방지막 형성용 유기 중합체 및 이를 포함하는 유기 조성물 |
| EP1762895B1 (en) * | 2005-08-29 | 2016-02-24 | Rohm and Haas Electronic Materials, L.L.C. | Antireflective Hard Mask Compositions |
| KR100703007B1 (ko) | 2005-11-17 | 2007-04-06 | 삼성전자주식회사 | 감광성 유기 반사 방지막 형성용 조성물 및 이를 이용한패턴 형성 방법 |
| KR100871770B1 (ko) * | 2007-09-12 | 2008-12-05 | 주식회사 효성 | 안트라세닐 벤질기 발색단을 포함하는 공중합체, 상기공중합체의 제조방법, 상기 공중합체를 포함하는유기반사방지막 조성물 및 상기 조성물을 포함하는유기반사방지막 |
| KR100920886B1 (ko) * | 2007-12-13 | 2009-10-09 | 주식회사 효성 | 현상 가능한 유기 반사방지막 형성용 조성물 및 이로부터형성된 유기 반사방지막 |
| KR100952465B1 (ko) * | 2007-12-18 | 2010-04-13 | 제일모직주식회사 | 방향족 (메타)아크릴레이트 화합물 및 감광성 고분자, 및레지스트 조성물 |
| KR101585992B1 (ko) * | 2007-12-20 | 2016-01-19 | 삼성전자주식회사 | 반사방지 코팅용 고분자, 반사방지 코팅용 조성물 및 이를 이용한 반도체 장치의 패턴 형성 방법 |
| KR100975913B1 (ko) * | 2008-10-31 | 2010-08-13 | 한국전자통신연구원 | 유기 박막 트랜지스터용 조성물, 이를 이용하여 형성된 유기 박막 트랜지스터 및 그 형성방법 |
| CN105732883B (zh) * | 2016-03-01 | 2018-07-03 | 中国科学技术大学 | 一种发射室温磷光的水性聚丙烯酸酯的制备方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2415823A1 (fr) * | 1978-01-27 | 1979-08-24 | Eastman Kodak Co | Composition photoreticulable contenant un polymere a groupe carbonyle, produit photosensible obtenu a partir de cette composition et procede de formation d'image qui utilise ce produit |
| DE2848967A1 (de) * | 1978-11-11 | 1980-05-22 | Basf Ag | Aromatische aldehydgruppen enthaltende polymerisate |
| US4822718A (en) | 1982-09-30 | 1989-04-18 | Brewer Science, Inc. | Light absorbing coating |
| US5674648A (en) | 1984-08-06 | 1997-10-07 | Brewer Science, Inc. | Anti-reflective coating |
| DE3528930A1 (de) * | 1985-08-13 | 1987-02-26 | Hoechst Ag | Polymere verbindungen und diese enthaltendes strahlungsempfindliches gemisch |
| AU633624B2 (en) * | 1989-09-22 | 1993-02-04 | National Starch And Chemical Investment Holding Corporation | Monomers and polymers containing acetal and aldehyde groups |
| US5258477A (en) * | 1989-09-22 | 1993-11-02 | National Starch And Chemical Investment Holding Corporation | Monomers and polymers containing acetal and aldehyde groups |
| 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 |
| EP0659781A3 (de) * | 1993-12-21 | 1995-09-27 | Ciba Geigy Ag | Maleinimidcopolymere, insbesonder für Photoresists. |
| JP3579946B2 (ja) * | 1995-02-13 | 2004-10-20 | Ｊｓｒ株式会社 | 化学増幅型感放射線性樹脂組成物 |
| FR2736061B1 (fr) * | 1995-06-27 | 1997-08-08 | Thomson Csf | Materiau electroluminescent a base de polymere, procede de fabrication et diode electroluminescente utilisant ce materiau |
| CA2205099A1 (en) * | 1996-05-24 | 1997-11-24 | Patricia Marie Lesko | Fluorescent polymers and coating compositions |
| US5886102A (en) * | 1996-06-11 | 1999-03-23 | Shipley Company, L.L.C. | Antireflective coating compositions |
| US7147983B1 (en) * | 1996-10-07 | 2006-12-12 | Shipley Company, L.L.C. | Dyed photoresists and methods and articles of manufacture comprising same |
| US5981145A (en) * | 1997-04-30 | 1999-11-09 | Clariant Finance (Bvi) Limited | Light absorbing polymers |
| TW457403B (en) * | 1998-07-03 | 2001-10-01 | Clariant Int Ltd | Composition for forming a radiation absorbing coating containing blocked isocyanate compound and anti-reflective coating formed therefrom |
| KR100465864B1 (ko) * | 1999-03-15 | 2005-01-24 | 주식회사 하이닉스반도체 | 유기 난반사방지 중합체 및 그의 제조방법 |
-
1999
- 1999-04-23 KR KR10-1999-0014763A patent/KR100395904B1/ko not_active IP Right Cessation
- 1999-11-17 TW TW088120015A patent/TW546318B/zh not_active IP Right Cessation
- 1999-11-26 GB GB9927833A patent/GB2349148B/en not_active Expired - Fee Related
- 1999-12-14 JP JP35449399A patent/JP3851476B2/ja not_active Expired - Fee Related
- 1999-12-15 IT IT1999TO001099A patent/IT1308674B1/it active
- 1999-12-15 CN CNB991263812A patent/CN1215094C/zh not_active Expired - Fee Related
- 1999-12-23 DE DE19962784A patent/DE19962784A1/de not_active Ceased
- 1999-12-23 DE DE19964382A patent/DE19964382B4/de not_active Expired - Fee Related
-
2000
- 2000-01-13 FR FR0000392A patent/FR2792633B1/fr not_active Expired - Fee Related
- 2000-02-09 US US09/501,049 patent/US6368768B1/en not_active Expired - Fee Related
- 2000-04-20 NL NL1014997A patent/NL1014997C2/nl not_active IP Right Cessation
- 2000-06-13 FR FR0007514A patent/FR2793244A1/fr active Pending
- 2000-06-13 FR FR0007516A patent/FR2793255B1/fr not_active Expired - Fee Related
- 2000-06-13 FR FR0007511A patent/FR2793254B1/fr not_active Expired - Fee Related
-
2002
- 2002-01-22 US US10/054,837 patent/US20020132183A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP2001098024A (ja) | 2001-04-10 |
| ITTO991099A0 (it) | 1999-12-15 |
| US6368768B1 (en) | 2002-04-09 |
| DE19964382B4 (de) | 2008-08-14 |
| FR2793254A1 (fr) | 2000-11-10 |
| ITTO991099A1 (it) | 2001-06-15 |
| US20020132183A1 (en) | 2002-09-19 |
| NL1014997C2 (nl) | 2001-06-26 |
| GB9927833D0 (en) | 2000-01-26 |
| KR100395904B1 (ko) | 2003-08-27 |
| DE19962784A1 (de) | 2000-10-26 |
| IT1308674B1 (it) | 2002-01-09 |
| FR2792633A1 (fr) | 2000-10-27 |
| FR2793254B1 (fr) | 2006-09-22 |
| GB2349148B (en) | 2004-08-04 |
| FR2793244A1 (fr) | 2000-11-10 |
| CN1215094C (zh) | 2005-08-17 |
| GB2349148A (en) | 2000-10-25 |
| TW546318B (en) | 2003-08-11 |
| FR2793255B1 (fr) | 2006-09-22 |
| NL1014997A1 (nl) | 2000-10-24 |
| FR2792633B1 (fr) | 2007-06-08 |
| CN1271720A (zh) | 2000-11-01 |
| FR2793255A1 (fr) | 2000-11-10 |
| KR20000067184A (ko) | 2000-11-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3851476B2 (ja) | 有機反射防止重合体およびその製造方法 | |
| JP4808597B2 (ja) | 有機反射防止重合体およびその製造方法 | |
| JP4121683B2 (ja) | 反射防止膜用組成物、反射防止膜の製造方法、および半導体素子 | |
| JP4253088B2 (ja) | 反射防止膜組成物およびその準備方法、ならびに反射防止膜およびその形成方法 | |
| JP3860411B2 (ja) | 乱反射防止膜用重合体とその製造方法 | |
| JP4463417B2 (ja) | 有機反射防止膜用重合体及びその製造方法 | |
| JP4107937B2 (ja) | 反射防止膜の組成物、反射防止膜の製造方法及び半導体素子 | |
| JP3960750B2 (ja) | 有機反射防止化合物及びその製造方法 | |
| JP3602077B2 (ja) | 有機反射防止膜の組成物及びその製造方法 | |
| JP3848551B2 (ja) | 有機反射防止膜の組成物及びその製造方法 | |
| JP3602075B2 (ja) | 有機反射防止膜の組成物及びその製造方法 | |
| KR100367399B1 (ko) | 유기난반사방지중합체및그의제조방법 | |
| KR100351458B1 (ko) | 유기 반사방지 중합체 및 그의 제조방법 | |
| KR100721181B1 (ko) | 유기반사방지막 조성물 및 그의 제조방법 | |
| KR100400242B1 (ko) | 유기난반사방지중합체및그의제조방법 | |
| KR100351459B1 (ko) | 유기 반사방지 중합체 및 그의 제조방법 | |
| KR100515485B1 (ko) | Ｉ-라인 포토레지스트용 유기반사방지막 조성물 | |
| KR20020059261A (ko) | 유기 반사방지 화합물 및 그의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20050713 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20050726 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20051026 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20051031 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20060126 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20060808 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20060901 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| LAPS | Cancellation because of no payment of annual fees |