TWI538902B - 鎓化合物及其合成方法 - Google Patents
鎓化合物及其合成方法 Download PDFInfo
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- TWI538902B TWI538902B TW102133124A TW102133124A TWI538902B TW I538902 B TWI538902 B TW I538902B TW 102133124 A TW102133124 A TW 102133124A TW 102133124 A TW102133124 A TW 102133124A TW I538902 B TWI538902 B TW I538902B
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- 238000000034 method Methods 0.000 title claims description 35
- 150000004010 onium ions Chemical class 0.000 title claims description 4
- 230000015572 biosynthetic process Effects 0.000 title description 9
- 238000003786 synthesis reaction Methods 0.000 title description 8
- -1 phosphonium salt compound Chemical class 0.000 claims description 105
- 229920002120 photoresistant polymer Polymers 0.000 claims description 79
- 239000000203 mixture Substances 0.000 claims description 42
- 229920000642 polymer Polymers 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 22
- 239000010410 layer Substances 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 230000005855 radiation Effects 0.000 claims description 18
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 18
- 239000000758 substrate Substances 0.000 claims description 16
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 150000003304 ruthenium compounds Chemical class 0.000 claims description 9
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- 230000003213 activating effect Effects 0.000 claims description 5
- 150000004714 phosphonium salts Chemical class 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000011247 coating layer Substances 0.000 claims description 3
- 239000012530 fluid Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000005647 linker group Chemical group 0.000 claims description 2
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 150000001622 bismuth compounds Chemical class 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 238000000206 photolithography Methods 0.000 claims 1
- 239000002253 acid Substances 0.000 description 35
- 239000000178 monomer Substances 0.000 description 24
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 22
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- 238000003384 imaging method Methods 0.000 description 6
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 6
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- 125000003367 polycyclic group Chemical group 0.000 description 4
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- 229910052715 tantalum Inorganic materials 0.000 description 3
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-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
- 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
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- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
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- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 2
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- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials For Photolithography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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| US201261701612P | 2012-09-15 | 2012-09-15 |
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| TW201418199A TW201418199A (zh) | 2014-05-16 |
| TWI538902B true TWI538902B (zh) | 2016-06-21 |
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| TW102133124A TWI538902B (zh) | 2012-09-15 | 2013-09-13 | 鎓化合物及其合成方法 |
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| JP (3) | JP6144164B2 (OSRAM) |
| KR (2) | KR20140036118A (OSRAM) |
| CN (2) | CN103664870B (OSRAM) |
| TW (1) | TWI538902B (OSRAM) |
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| JP6144164B2 (ja) * | 2012-09-15 | 2017-06-07 | ローム アンド ハース エレクトロニック マテリアルズ エルエルシーRohm and Haas Electronic Materials LLC | オニウム化合物およびその合成方法 |
| JP5790631B2 (ja) * | 2012-12-10 | 2015-10-07 | 信越化学工業株式会社 | スルホニウム塩及び高分子化合物、レジスト材料及びパターン形成方法、並びに該高分子化合物の製造方法 |
| US10179778B2 (en) | 2013-09-27 | 2019-01-15 | Rohm And Haas Electronic Materials Llc | Substituted aryl onium materials |
| IL296766A (en) * | 2020-03-30 | 2022-11-01 | Fujifilm Corp | Actinic beam-sensitive or radiation-sensitive resin composition, method for creating a pattern, resistant layer and method for manufacturing an electronic device |
| JP7719654B2 (ja) * | 2020-08-05 | 2025-08-06 | 住友化学株式会社 | 塩、酸発生剤、レジスト組成物及びレジストパターンの製造方法 |
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| DE60230679D1 (de) | 2002-03-04 | 2009-02-12 | Wako Pure Chem Ind Ltd | Heterocyclustragende oniumsalze |
| US7160669B2 (en) * | 2002-10-16 | 2007-01-09 | Sumitomo Chemical Company, Limited | Chemical amplification type resist composition |
| US7217492B2 (en) | 2002-12-25 | 2007-05-15 | Jsr Corporation | Onium salt compound and radiation-sensitive resin composition |
| TWI412888B (zh) * | 2006-08-18 | 2013-10-21 | Sumitomo Chemical Co | 適合作為酸產生劑之鹽及含有該鹽之化學放大型正光阻組成物 |
| JP5116311B2 (ja) * | 2007-02-05 | 2013-01-09 | 東洋合成工業株式会社 | スルホニウム塩 |
| JP5453834B2 (ja) * | 2008-02-22 | 2014-03-26 | 住友化学株式会社 | エステル化合物及びその製造方法 |
| JP5208573B2 (ja) * | 2008-05-06 | 2013-06-12 | サンアプロ株式会社 | スルホニウム塩、光酸発生剤、光硬化性組成物及びこの硬化体 |
| JP5481046B2 (ja) * | 2008-08-13 | 2014-04-23 | 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、新規な化合物および酸発生剤 |
| JP5201363B2 (ja) * | 2008-08-28 | 2013-06-05 | 信越化学工業株式会社 | 重合性アニオンを有するスルホニウム塩及び高分子化合物、レジスト材料及びパターン形成方法 |
| JP5469920B2 (ja) * | 2009-05-29 | 2014-04-16 | 東京応化工業株式会社 | レジスト組成物及びレジストパターン形成方法 |
| JP5635526B2 (ja) * | 2009-10-26 | 2014-12-03 | 株式会社Adeka | 芳香族スルホニウム塩化合物 |
| KR101761434B1 (ko) * | 2009-12-08 | 2017-07-25 | 제이에스알 가부시끼가이샤 | 감방사선성 수지 조성물, 중합체, 단량체 및 감방사선성 수지 조성물의 제조 방법 |
| WO2011093471A1 (ja) * | 2010-01-29 | 2011-08-04 | タカノ株式会社 | ネオポンコラノール類の製造方法 |
| JP5763433B2 (ja) * | 2010-06-29 | 2015-08-12 | 住友化学株式会社 | 塩、酸発生剤、レジスト組成物及びレジストパターンの製造方法 |
| JP5517811B2 (ja) * | 2010-07-26 | 2014-06-11 | サンアプロ株式会社 | 化学増幅型ネガ型フォトレジスト組成物 |
| JP5960991B2 (ja) | 2011-01-28 | 2016-08-02 | 住友化学株式会社 | 塩、レジスト組成物及びレジストパターンの製造方法 |
| JP5906787B2 (ja) | 2011-03-08 | 2016-04-20 | 住友化学株式会社 | 塩、レジスト組成物及びレジストパターンの製造方法 |
| PT105584B (pt) * | 2011-03-28 | 2013-08-30 | Hovione Farmaciencia S A | Reagentes electrofílicos de alquilação, a sua preparação e usos |
| TWI545118B (zh) | 2012-09-15 | 2016-08-11 | 羅門哈斯電子材料有限公司 | 酸產生劑化合物及包含該化合物之光阻劑 |
| JP6144164B2 (ja) * | 2012-09-15 | 2017-06-07 | ローム アンド ハース エレクトロニック マテリアルズ エルエルシーRohm and Haas Electronic Materials LLC | オニウム化合物およびその合成方法 |
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| JP6144164B2 (ja) | 2017-06-07 |
| US20180052390A1 (en) | 2018-02-22 |
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| JP6343270B2 (ja) | 2018-06-13 |
| KR20160032074A (ko) | 2016-03-23 |
| TW201418199A (zh) | 2014-05-16 |
| US20140080056A1 (en) | 2014-03-20 |
| KR102012203B1 (ko) | 2019-08-20 |
| JP2016106073A (ja) | 2016-06-16 |
| CN103664870A (zh) | 2014-03-26 |
| JP2017105803A (ja) | 2017-06-15 |
| KR20140036118A (ko) | 2014-03-25 |
| CN107266415A (zh) | 2017-10-20 |
| JP2014097969A (ja) | 2014-05-29 |
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