JP2010002633A - レジスト組成物 - Google Patents
レジスト組成物 Download PDFInfo
- Publication number
- JP2010002633A JP2010002633A JP2008160865A JP2008160865A JP2010002633A JP 2010002633 A JP2010002633 A JP 2010002633A JP 2008160865 A JP2008160865 A JP 2008160865A JP 2008160865 A JP2008160865 A JP 2008160865A JP 2010002633 A JP2010002633 A JP 2010002633A
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- Prior art keywords
- resist composition
- polymer
- acid
- resist
- monomer
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 57
- 229920000642 polymer Polymers 0.000 claims abstract description 56
- 239000002245 particle Substances 0.000 claims abstract description 35
- 239000002253 acid Substances 0.000 claims abstract description 24
- 239000000178 monomer Substances 0.000 claims description 69
- 239000000539 dimer Substances 0.000 claims description 29
- 239000013638 trimer Substances 0.000 claims description 27
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 239000000243 solution Substances 0.000 abstract description 23
- 230000007547 defect Effects 0.000 abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 18
- 238000001459 lithography Methods 0.000 abstract description 10
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- 238000004821 distillation Methods 0.000 description 22
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- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- 239000000654 additive Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
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- 238000002834 transmittance Methods 0.000 description 4
- FDYDISGSYGFRJM-UHFFFAOYSA-N (2-methyl-2-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC1C(OC(=O)C(=C)C)(C)C2C3 FDYDISGSYGFRJM-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 3
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- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- BDFAOUQQXJIZDG-UHFFFAOYSA-N 2-methylpropane-1-thiol Chemical compound CC(C)CS BDFAOUQQXJIZDG-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 2
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
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- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
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- 125000003158 alcohol group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000012986 chain transfer agent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
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- 229920001577 copolymer Polymers 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 238000000609 electron-beam lithography Methods 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
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- 150000002430 hydrocarbons Chemical group 0.000 description 2
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- 125000005647 linker group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
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- JANRUIBBIKVUHU-UHFFFAOYSA-N (4-methyl-2-oxooxan-4-yl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1(C)CCOC(=O)C1 JANRUIBBIKVUHU-UHFFFAOYSA-N 0.000 description 1
- OJEDADOVBFGHOI-UHFFFAOYSA-N (4-methyl-2-oxooxolan-3-yl) 2-methylprop-2-enoate Chemical compound CC1COC(=O)C1OC(=O)C(C)=C OJEDADOVBFGHOI-UHFFFAOYSA-N 0.000 description 1
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- MJEDTBDGYVATPI-UHFFFAOYSA-N 4-hydroxy-TEMPO benzoate Chemical group C1C(C)(C)N([O])C(C)(C)CC1OC(=O)C1=CC=CC=C1 MJEDTBDGYVATPI-UHFFFAOYSA-N 0.000 description 1
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- FFBAOWPGDUCRHT-UHFFFAOYSA-N C(C1=CC=CC=C1)S(=O)(=O)[O-].OC1=C(C=CC=C1)[SH+]CCC1=CC=CC=C1 Chemical compound C(C1=CC=CC=C1)S(=O)(=O)[O-].OC1=C(C=CC=C1)[SH+]CCC1=CC=CC=C1 FFBAOWPGDUCRHT-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical class C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- ASMQGLCHMVWBQR-UHFFFAOYSA-N Diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(O)OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- 101150043805 HADHA gene Proteins 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
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- YSDWRYAKIVBJRH-UHFFFAOYSA-N P(O)(O)=O.COP(OC)=O Chemical class P(O)(O)=O.COP(OC)=O YSDWRYAKIVBJRH-UHFFFAOYSA-N 0.000 description 1
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
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| JP2001192355A (ja) * | 1999-10-27 | 2001-07-17 | Daicel Chem Ind Ltd | 環式骨格を有する（メタ）アクリル酸エステルの製造法 |
| JP2004143281A (ja) * | 2002-10-24 | 2004-05-20 | Maruzen Petrochem Co Ltd | レジスト用ポリマー及び感放射線性レジスト組成物 |
| JP2004323704A (ja) * | 2003-04-25 | 2004-11-18 | Daicel Chem Ind Ltd | フォトレジスト用重合体合成用（メタ）アクリル酸エステルとその製造法 |
| JP2005173252A (ja) * | 2003-12-11 | 2005-06-30 | Maruzen Petrochem Co Ltd | レジスト用ポリマー溶液およびその製造方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2001192355A (ja) * | 1999-10-27 | 2001-07-17 | Daicel Chem Ind Ltd | 環式骨格を有する（メタ）アクリル酸エステルの製造法 |
| JP2004143281A (ja) * | 2002-10-24 | 2004-05-20 | Maruzen Petrochem Co Ltd | レジスト用ポリマー及び感放射線性レジスト組成物 |
| JP2004323704A (ja) * | 2003-04-25 | 2004-11-18 | Daicel Chem Ind Ltd | フォトレジスト用重合体合成用（メタ）アクリル酸エステルとその製造法 |
| JP2005173252A (ja) * | 2003-12-11 | 2005-06-30 | Maruzen Petrochem Co Ltd | レジスト用ポリマー溶液およびその製造方法 |
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| JP2022175368A (ja) * | 2021-05-13 | 2022-11-25 | 信越化学工業株式会社 | 化学増幅型レジスト組成物、フォトマスクブランク、レジストパターンの形成方法、及び高分子化合物の製造方法 |
| JP2025039683A (ja) * | 2021-05-13 | 2025-03-21 | 信越化学工業株式会社 | 重合性単量体、高分子化合物、化学増幅型レジスト組成物、フォトマスクブランク、及びレジストパターンの形成方法 |
| JP7656485B2 (ja) | 2021-05-13 | 2025-04-03 | 信越化学工業株式会社 | 高分子化合物の製造方法 |
| US12429772B2 (en) | 2021-05-13 | 2025-09-30 | Shin-Etsu Chemical Co., Ltd. | Chemically amplified resist composition, photomask blank, method for forming resist pattern, and method for producing polymer compound |
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