JP6637548B2 - オーバーコートされたフォトレジストと共に用いるためのコーティング組成物 - Google Patents
オーバーコートされたフォトレジストと共に用いるためのコーティング組成物 Download PDFInfo
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- JP6637548B2 JP6637548B2 JP2018103790A JP2018103790A JP6637548B2 JP 6637548 B2 JP6637548 B2 JP 6637548B2 JP 2018103790 A JP2018103790 A JP 2018103790A JP 2018103790 A JP2018103790 A JP 2018103790A JP 6637548 B2 JP6637548 B2 JP 6637548B2
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- 229920002120 photoresistant polymer Polymers 0.000 title claims description 82
- 239000008199 coating composition Substances 0.000 title claims description 59
- 239000000203 mixture Substances 0.000 claims description 65
- 229920005989 resin Polymers 0.000 claims description 52
- 239000011347 resin Substances 0.000 claims description 52
- 239000000758 substrate Substances 0.000 claims description 35
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical group O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 27
- 239000003153 chemical reaction reagent Substances 0.000 claims description 18
- 125000001142 dicarboxylic acid group Chemical group 0.000 claims description 15
- 230000003667 anti-reflective effect Effects 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 239000006117 anti-reflective coating Substances 0.000 claims description 10
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 230000000379 polymerizing effect Effects 0.000 claims description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- 239000003431 cross linking reagent Substances 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 229940035893 uracil Drugs 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 239000002253 acid Substances 0.000 description 40
- 229920000642 polymer Polymers 0.000 description 37
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- 125000000217 alkyl group Chemical group 0.000 description 24
- 239000000243 solution Substances 0.000 description 20
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- -1 alkyl aldehyde Chemical class 0.000 description 18
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- 229910052739 hydrogen Inorganic materials 0.000 description 17
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- 229910052731 fluorine Inorganic materials 0.000 description 11
- 235000012431 wafers Nutrition 0.000 description 11
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
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- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 8
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- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
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- 239000004971 Cross linker Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
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- 230000003213 activating effect Effects 0.000 description 6
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- 229910052736 halogen Chemical group 0.000 description 6
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- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 6
- 125000002950 monocyclic group Chemical group 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 229920000877 Melamine resin Polymers 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
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- 238000012545 processing Methods 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 description 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 4
- 150000004767 nitrides Chemical class 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 4
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 description 3
- XGQJGMGAMHFMAO-UHFFFAOYSA-N 1,3,4,6-tetrakis(methoxymethyl)-3a,6a-dihydroimidazo[4,5-d]imidazole-2,5-dione Chemical compound COCN1C(=O)N(COC)C2C1N(COC)C(=O)N2COC XGQJGMGAMHFMAO-UHFFFAOYSA-N 0.000 description 3
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-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
- 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229920003270 Cymel® Polymers 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000004699 Ultra-high molecular weight polyethylene Substances 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 125000005157 alkyl carboxy group Chemical group 0.000 description 3
- 125000005233 alkylalcohol group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 230000008033 biological extinction Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
- 150000007942 carboxylates Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 238000000671 immersion lithography Methods 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 238000004377 microelectronic Methods 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 125000006413 ring segment Chemical group 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 229920000785 ultra high molecular weight polyethylene Polymers 0.000 description 3
- 238000001039 wet etching Methods 0.000 description 3
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 2
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 2
- HENCHDCLZDQGIQ-UHFFFAOYSA-N 3-[3,5-bis(2-carboxyethyl)-2,4,6-trioxo-1,3,5-triazinan-1-yl]propanoic acid Chemical compound OC(=O)CCN1C(=O)N(CCC(O)=O)C(=O)N(CCC(O)=O)C1=O HENCHDCLZDQGIQ-UHFFFAOYSA-N 0.000 description 2
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- XYVQFUJDGOBPQI-UHFFFAOYSA-N Methyl-2-hydoxyisobutyric acid Chemical compound COC(=O)C(C)(C)O XYVQFUJDGOBPQI-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- FLJPGEWQYJVDPF-UHFFFAOYSA-L caesium sulfate Chemical compound [Cs+].[Cs+].[O-]S([O-])(=O)=O FLJPGEWQYJVDPF-UHFFFAOYSA-L 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000002993 cycloalkylene group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001312 dry etching Methods 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 229940116333 ethyl lactate Drugs 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 150000002466 imines Chemical class 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229920005596 polymer binder Polymers 0.000 description 2
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- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 150000004072 triols Chemical class 0.000 description 2
- MCJPJAJHPRCILL-UHFFFAOYSA-N (2,6-dinitrophenyl)methyl 4-methylbenzenesulfonate Chemical class C1=CC(C)=CC=C1S(=O)(=O)OCC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O MCJPJAJHPRCILL-UHFFFAOYSA-N 0.000 description 1
- MSLTZKLJPHUCPU-WNQIDUERSA-M (2s)-2-hydroxypropanoate;tetrabutylazanium Chemical compound C[C@H](O)C([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MSLTZKLJPHUCPU-WNQIDUERSA-M 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 1
- LJHFIVQEAFAURQ-ZPUQHVIOSA-N (NE)-N-[(2E)-2-hydroxyiminoethylidene]hydroxylamine Chemical class O\N=C\C=N\O LJHFIVQEAFAURQ-ZPUQHVIOSA-N 0.000 description 1
- VPVXHAANQNHFSF-UHFFFAOYSA-N 1,4-dioxan-2-one Chemical group O=C1COCCO1 VPVXHAANQNHFSF-UHFFFAOYSA-N 0.000 description 1
- CWKVFRNCODQPDB-UHFFFAOYSA-N 1-(2-aminoethylamino)propan-2-ol Chemical compound CC(O)CNCCN CWKVFRNCODQPDB-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
- HMNZROFMBSUMAB-UHFFFAOYSA-N 1-ethoxybutan-1-ol Chemical compound CCCC(O)OCC HMNZROFMBSUMAB-UHFFFAOYSA-N 0.000 description 1
- JLBXCKSMESLGTJ-UHFFFAOYSA-N 1-ethoxypropan-1-ol Chemical compound CCOC(O)CC JLBXCKSMESLGTJ-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 1
- QMBSJPZHUJCMJU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)propanoic acid Chemical compound CCOCCOC(C)C(O)=O QMBSJPZHUJCMJU-UHFFFAOYSA-N 0.000 description 1
- DRLRGHZJOQGQEC-UHFFFAOYSA-N 2-(2-methoxypropoxy)propyl acetate Chemical compound COC(C)COC(C)COC(C)=O DRLRGHZJOQGQEC-UHFFFAOYSA-N 0.000 description 1
- QRHHZFRCJDAUNA-UHFFFAOYSA-N 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C1=CC(OC)=CC=C1C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 QRHHZFRCJDAUNA-UHFFFAOYSA-N 0.000 description 1
- QTUVQQKHBMGYEH-UHFFFAOYSA-N 2-(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC=NC=N1 QTUVQQKHBMGYEH-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- QBPRLLDEHWSITF-UHFFFAOYSA-N 2-methoxyethyl propaneperoxoate Chemical compound COCCOOC(CC)=O QBPRLLDEHWSITF-UHFFFAOYSA-N 0.000 description 1
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical compound OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 description 1
- JSGVZVOGOQILFM-UHFFFAOYSA-N 3-methoxy-1-butanol Chemical compound COC(C)CCO JSGVZVOGOQILFM-UHFFFAOYSA-N 0.000 description 1
- HYKBUMWQWWRXJN-UHFFFAOYSA-N 4-[2-(2-nitrophenyl)ethyl]benzenesulfonic acid Chemical class C1=CC(S(=O)(=O)O)=CC=C1CCC1=CC=CC=C1[N+]([O-])=O HYKBUMWQWWRXJN-UHFFFAOYSA-N 0.000 description 1
- NFGPNZVXBBBZNF-UHFFFAOYSA-N 4-[2-(4-aminophenyl)propan-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(N)C=C1 NFGPNZVXBBBZNF-UHFFFAOYSA-N 0.000 description 1
- MMVUZMIOJNPDME-UHFFFAOYSA-N 4-methylbenzenesulfonate;triethylazanium Chemical compound CC[NH+](CC)CC.CC1=CC=C(S([O-])(=O)=O)C=C1 MMVUZMIOJNPDME-UHFFFAOYSA-N 0.000 description 1
- YXZXRYDYTRYFAF-UHFFFAOYSA-M 4-methylbenzenesulfonate;triphenylsulfanium Chemical class CC1=CC=C(S([O-])(=O)=O)C=C1.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 YXZXRYDYTRYFAF-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
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- C08G18/092—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture oligomerisation to isocyanurate groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/166—Catalysts not provided for in the groups C08G18/18 - C08G18/26
- C08G18/168—Organic compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
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- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
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- C09D201/025—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
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- C09D201/08—Carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
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- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
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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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
-
- 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
- G03F7/16—Coating processes; Apparatus therefor
- G03F7/162—Coating on a rotating support, e.g. using a whirler or a spinner
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/20—Exposure; Apparatus therefor
-
- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
Description
R1は、水素、−C(O)R、−C(O)OR、置換もしくは非置換C1−C12アルキル(例えば、非置換C1−C12アルキル及びC1−C12ハロアルキル)、置換もしくは非置換2〜5員ヘテロアルキル(例えば、置換もしくは非置換C1−C12アルキルアルコール、置換もしくは非置換C1−C12アルキルカルボキシ、置換もしくは非置換C1−C12アルキルエステル、置換もしくは非置換C1−C12アルキルアミン、または置換もしくは非置換C1−C12アルキルアルデヒド)、置換もしくは非置換C3−C6シクロアルキル、置換もしくは非置換5〜6員ヘテロシクロアルキル、置換もしくは非置換フェニル、または置換もしくは非置換5〜6員ヘテロアリールであり得る。
n1及びn2は、独立して、0〜100の整数であり得、
Q1は、独立した結合、−O−、−S−、−NHR−、または−CRR´−であり得、
A1、A2、A3、及びA4は、独立して、水素、脂肪族基(例えば、C1−C12アルキル)、または置換もしくは非置換C1−C12ヘテロアルキル(例えば、C1−C12アルキルアルコール)であり得、
R及びR´は、本明細書で記載される。
様々な樹脂が下地コーティング組成物の樹脂成分として作用し得る。
下地コーティング組成物と共に使用するためのフォトレジストは典型的にポリマーと1つ以上の酸発生剤とを含む。一般的に好ましいのはポジ型レジストであり、レジストポリマーはレジスト組成物にアルカリ性の水溶解性を与える官能基を有する。例えば、好まれるのは、ヒドロキシルまたはカルボキシレート等の極性官能基、またはリソグラフィ加工のときにかかる極性部分を遊離させることができる酸不安定基を含む、ポリマーである。好ましくは、ポリマーは、水性アルカリ溶液で現像可能なレジストを行うのに十分な量でレジスト組成物に用いられる。
使用において、本発明のコーティング組成物は、スピンコーティング等の多種多様の方法の任意のものによって、コーティング層として基板に塗布される。一般的なコーティング組成物は、基板上に、約0.02〜0.5μmの乾燥層厚さ、好ましくは約0.04〜0.20μmの乾燥層厚さで塗布される。基板は好適に、フォトレジストを伴う処理に用いられる任意の基板である。例えば、基板は、ケイ素、二酸化ケイ素、またはアルミニウム−酸化アルミニウムマイクロ電子ウェハであり得る。また、ガリウムヒ素、炭化ケイ素、セラミック、石英、または銅基板を使用してもよい。液晶ディスプレイまたは他のフラットパネルディスプレイ用途のための基板、例えばガラス基板、インジウムスズ酸化物でコーティングされた基板等も、好適に使用される。光学及び光学電子デバイス(例えば、導波管)のための基板もまた、使用可能である。
比較用ポリマー実施例1
250mlの三つ口丸底フラスコを、14.6gのトリス(2−ヒドロキシエチル)イソシアヌレート、5.4gの5−ニトロウラシル、9.4gのジグリコール酸、10.6gの1,2−プロパンジオール、触媒としての0.53gのパラ−トルエンスルホン酸モノ−ハイドレート、溶剤としての40gのアニソールで満たした。それを設定温度(150℃)まで攪拌しながら加熱した。反応混合物を9時間熱したあと、次いで溶液を室温に冷却した。未加工の溶液を単離のためTHF(80g)で希釈した。反応混合物をイソプロピルアルコール(x10超の反応混合物)で析出し、次いでろ過し、40℃で24時間真空乾燥させた。完全乾燥粉末を15重量%に希釈した。第2の単離ステップは、第1のステップと同じである。
比較用BARC実施例1
3.198gの比較用ポリマー1、架橋剤としての0.570gのテトラメトキシメチルグリコルリル、0.030gのアンモニウムp−トルエンスルホン酸塩、及びレベリング剤としての0.002gのポリフォックス656を、96.2gの混合物溶媒(HBM/GBL90/10重量/重量)に溶解して、溶液を得た。調製されたすべての溶液を、超高分子量ポリエチレン膜フィルタを通して濾過した。スピナーを使用するシリコンウェハ上に溶液をコーティングし、ウェハをホットプレート上で205℃で1分間加熱して、反射防止コーティングを形成した。分光エリプソメータによる反射防止コーティングの測定は、193nmで1.89の屈折率n及び0.29の光学消衰係数kを示した。
5.583gの比較用ポリマー2、架橋剤としての0.297gのテトラメトキシメチルグリコルリル、0.047gのトライ−エチルアンモニウムp−トルエンスルホン酸塩、及びレベリング剤としての0.003gのポリフォックス656を、94.07gのHBM溶媒に溶解して、溶液を得た。調製されたすべての溶液を、超高分子量ポリエチレン膜フィルタを通して濾過した。スピナーを使用するシリコンウェハ上に溶液をコーティングし、ウェハをホットプレート上で205℃で1分間加熱して、反射防止コーティングを形成した。分光エリプソメータによる反射防止コーティングの測定は、193nmで1.96の屈折率n及び0.29の光学消衰係数kを示した。
3.407gのポリマー1、架橋剤としての0.611gのテトラメトキシメチルグリコルリル、0.05gの2,4,6−トライメチルピリジニウムp−トルエンスルホン酸塩、及びレベリング剤としての0.002gのポリフォックス656を、95.93gのHBM溶媒に溶解して、溶液を得た。調製されたすべての溶液を、超高分子量ポリエチレン膜フィルタを通して濾過した。スピナーを使用するシリコンウェハ上に溶液をコーティングし、ウェハをホットプレート上で205℃で1分間加熱して、反射防止コーティングを形成した。分光エリプソメータによる反射防止コーティングの測定は、193nmで1.83の屈折率n及び0.20の光学消衰係数kを示した。
H2/N2を用いたエッチングレートは、以下の条件を使用してCCP型エッチング装置で決定した:12秒間のガス流れ400H2/700N2、20mTRF電力、温度:20℃。2つのウェハをBARCでコーティングし、1500rpmでスピンし、205℃でベークした。フィルムの厚さを測定した。次いで、BARCコーティングされたウェハを、12秒間エッチングした。各BARCのフィルムの厚さを再度測定した。組成物のポリマーの大西パラメータ値も計測された。結果は、図1及び以下の表1に示される。
Claims (14)
- コーティングされた基板であって、
(a)基板上のコーティング組成物の層であって、前記コーティング組成物が、1つ以上の置換ウラシル部分及び1つ以上の反応済みジカルボン酸基を含む樹脂を含み、前記樹脂が、1)1つ以上の置換ウラシル部分を含む第1の試薬、及び2)1つ以上の脂肪族ジカルボン酸基を含む第2の試薬を重合することによって得ることができる、コーティング組成物の層と、
(b)前記コーティング組成物の層上のフォトレジスト層と、を含む、基板。 - 前記樹脂が、1つ以上のイソシアヌレート部分をさらに含む、請求項1に記載の基板。
- ウラシル部分が、ハロまたはニトロ基で置換されている、請求項1または2に記載の基板。
- コーティングされた基板であって、
(a)基板上のコーティング組成物の層であって、前記コーティング組成物が、1つ以上の置換ウラシル部分及び1つ以上の反応済みジカルボン酸基を含む樹脂を含み、前記樹脂が、1)1つ以上の置換ウラシル部分を含む第1の試薬、2)1つ以上のジカルボン酸基を含む第2の試薬、及び3)1つ以上のイソシアヌレート部分を含む第3の試薬を重合することによって得ることができる、コーティング組成物の層と、
(b)前記コーティング組成物の層上のフォトレジスト層と、を含む、請求項1〜3のいずれか一項に記載の基板。 - ウラシル部分が、ハロまたはニトロ基で置換されている、請求項4に記載の基板。
- 前記樹脂が、樹脂の全重量に基づいて20〜70重量パーセントの量で前記ウラシル及び反応済みジカルボン酸の成分を含む、請求項1〜5のいずれか一項に記載の基板。
- 前記樹脂が、ポリエステル結合を含む、請求項1〜6のいずれか一項に記載の基板。
- フォトレジストレリーフ像を形成する方法であって、
(a)1つ以上の置換ウラシル部分及び1つ以上の反応済みジカルボン酸基を含む樹脂を含み、前記樹脂が、1)1つ以上の置換ウラシル部分を含む第1の試薬、及び2)1つ以上の脂肪族ジカルボン酸基を含む第2の試薬を重合することによって得ることができるコーティング組成物を、基板上に塗布することと、
(b)フォトレジスト組成物を前記コーティング組成物の層上に塗布することと、
(c)前記フォトレジスト層を露光及び現像して、レジストレリーフ像を提供することと、を含む、方法。 - フォトレジストレリーフ像を形成する方法であって、
(a)1つ以上の置換ウラシル部分及び1つ以上の反応済みジカルボン酸基を含む樹脂を含み、前記樹脂が、1)1つ以上の置換ウラシル部分を含む第1の試薬、2)1つ以上のジカルボン酸基を含む第2の試薬、及び3)1つ以上のイソシアヌレート部分を含む第3の試薬を重合することによって得ることができるコーティング組成物を、基板上に塗布することと、
(b)フォトレジスト組成物を前記コーティング組成物の層上に塗布することと、
(c)前記フォトレジスト層を露光及び現像して、レジストレリーフ像を提供することと、を含む、方法。 - オーバーコートされたフォトレジスト組成物と共に用いるための反射防止組成物であって、1つ以上の置換ウラシル部分及び1つ以上の反応済みジカルボン酸基を含む樹脂を含み、
前記樹脂が、1)1つ以上の置換ウラシル部分を含む第1の試薬、及び2)1つ以上の脂肪族ジカルボン酸基を含む第2の試薬を重合することによって得ることができる、反射防止組成物。 - 前記樹脂が、1つ以上のイソシアヌレート部分をさらに含む、請求項10に記載の反射防止組成物。
- オーバーコートされたフォトレジスト組成物と共に用いるための反射防止組成物であって、1つ以上の置換ウラシル部分及び1つ以上の反応済みジカルボン酸基を含む樹脂を含み、
前記樹脂が、1)1つ以上の置換ウラシル部分を含む第1の試薬、2)1つ以上のジカルボン酸基を含む第2の試薬、及び3)1つ以上のイソシアヌレート部分を含む第3の試薬を重合することによって得ることができる、反射防止組成物。 - 前記樹脂が、ポリエステル結合を含む、請求項10〜12のいずれか一項に記載の反射防止組成物。
- 前記組成物が、架橋剤成分を含む、請求項10〜13のいずれか一項に記載の反射防止組成物。
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