JP2010235600A5 - - Google Patents
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- JP2010235600A5 JP2010235600A5 JP2010054088A JP2010054088A JP2010235600A5 JP 2010235600 A5 JP2010235600 A5 JP 2010235600A5 JP 2010054088 A JP2010054088 A JP 2010054088A JP 2010054088 A JP2010054088 A JP 2010054088A JP 2010235600 A5 JP2010235600 A5 JP 2010235600A5
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- Prior art keywords
- ion
- group
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- general formula
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- 239000002253 acid Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- -1 polycyclic lactone Chemical class 0.000 description 34
- 125000000962 organic group Chemical group 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 125000002723 alicyclic group Chemical group 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 3
- 238000004293 19F NMR spectroscopy Methods 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 2
- 239000012953 triphenylsulfonium Substances 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- QWMFKVNJIYNWII-UHFFFAOYSA-N 5-bromo-2-(2,5-dimethylpyrrol-1-yl)pyridine Chemical compound CC1=CC=C(C)N1C1=CC=C(Br)C=N1 QWMFKVNJIYNWII-UHFFFAOYSA-N 0.000 description 1
- HICVVACJRYCFNX-UHFFFAOYSA-N 6-(cyclohexanecarbonyloxy)-1,1,2,2-tetrafluorohexane-1-sulfinic acid Chemical compound OS(=O)C(F)(F)C(F)(F)CCCCOC(=O)C1CCCCC1 HICVVACJRYCFNX-UHFFFAOYSA-N 0.000 description 1
- MYGITFWAQZLDQZ-UHFFFAOYSA-N 6-benzoyloxy-1,1,2,2-tetrafluorohexane-1-sulfonic acid N,N-diethylethanamine Chemical compound CCN(CC)CC.OS(=O)(=O)C(F)(F)C(F)(F)CCCCOC(=O)c1ccccc1 MYGITFWAQZLDQZ-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- SRLHDBRENZFCIN-UHFFFAOYSA-N n,n-di(butan-2-yl)butan-2-amine Chemical compound CCC(C)N(C(C)CC)C(C)CC SRLHDBRENZFCIN-UHFFFAOYSA-N 0.000 description 1
- CYQYCASVINMDFD-UHFFFAOYSA-N n,n-ditert-butyl-2-methylpropan-2-amine Chemical compound CC(C)(C)N(C(C)(C)C)C(C)(C)C CYQYCASVINMDFD-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- SUIWNNGQFUXAJL-UHFFFAOYSA-M sodium;6-(cyclohexanecarbonyloxy)-1,1,2,2-tetrafluorohexane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C(F)(F)C(F)(F)CCCCOC(=O)C1CCCCC1 SUIWNNGQFUXAJL-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-O tributylazanium Chemical compound CCCC[NH+](CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-O 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010054088A JP5549288B2 (ja) | 2009-03-12 | 2010-03-11 | フルオロアルカンスルホン酸アンモニウム塩類およびその製造方法 |
| KR1020117023367A KR20110123798A (ko) | 2009-03-12 | 2010-03-12 | 플루오로알칸술폰산암모늄염류 및 그 제조 방법 |
| PCT/JP2010/054245 WO2010104177A1 (ja) | 2009-03-12 | 2010-03-12 | フルオロアルカンスルホン酸アンモニウム塩類およびその製造方法 |
| US13/254,708 US8877960B2 (en) | 2009-03-12 | 2010-03-12 | Fluoroalkanesulfonic acid ammonium salts and method for producing same |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009058844 | 2009-03-12 | ||
| JP2009058844 | 2009-03-12 | ||
| JP2010054088A JP5549288B2 (ja) | 2009-03-12 | 2010-03-11 | フルオロアルカンスルホン酸アンモニウム塩類およびその製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010235600A JP2010235600A (ja) | 2010-10-21 |
| JP2010235600A5 true JP2010235600A5 (enExample) | 2011-11-24 |
| JP5549288B2 JP5549288B2 (ja) | 2014-07-16 |
Family
ID=42728462
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010054088A Active JP5549288B2 (ja) | 2009-03-12 | 2010-03-11 | フルオロアルカンスルホン酸アンモニウム塩類およびその製造方法 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US8877960B2 (enExample) |
| JP (1) | JP5549288B2 (enExample) |
| KR (1) | KR20110123798A (enExample) |
| WO (1) | WO2010104177A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG187076A1 (en) | 2010-07-30 | 2013-02-28 | Coopervision Int Holding Co Lp | Silicone hydrogel ophthalmic devices molded in vinyl alcohol copolymer molds and related methods |
| JP2012136507A (ja) * | 2010-11-15 | 2012-07-19 | Rohm & Haas Electronic Materials Llc | 塩基反応性光酸発生剤およびこれを含むフォトレジスト |
| EP2472322A2 (en) * | 2010-12-31 | 2012-07-04 | Rohm and Haas Electronic Materials LLC | Photoacid generating monomer and precursor thereof |
| US10831100B2 (en) | 2017-11-20 | 2020-11-10 | Rohm And Haas Electronic Materials, Llc | Iodine-containing photoacid generators and compositions comprising the same |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6749987B2 (en) | 2000-10-20 | 2004-06-15 | Fuji Photo Film Co., Ltd. | Positive photosensitive composition |
| JP4150509B2 (ja) | 2000-11-20 | 2008-09-17 | 富士フイルム株式会社 | ポジ型感光性組成物 |
| JP2004004561A (ja) | 2002-02-19 | 2004-01-08 | Sumitomo Chem Co Ltd | ポジ型レジスト組成物 |
| US6893792B2 (en) | 2002-02-19 | 2005-05-17 | Sumitomo Chemical Company, Limited | Positive resist composition |
| JP4103523B2 (ja) | 2002-09-27 | 2008-06-18 | Ｊｓｒ株式会社 | レジスト組成物 |
| TWI332122B (en) | 2005-04-06 | 2010-10-21 | Shinetsu Chemical Co | Novel sulfonate salts and derivatives, photoacid generators, resist compositions and patterning process |
| JP4816921B2 (ja) | 2005-04-06 | 2011-11-16 | 信越化学工業株式会社 | 新規スルホン酸塩及びその誘導体、光酸発生剤並びにこれを用いたレジスト材料及びパターン形成方法 |
| JP5124805B2 (ja) * | 2006-06-27 | 2013-01-23 | 信越化学工業株式会社 | 光酸発生剤並びにこれを用いたレジスト材料及びパターン形成方法 |
| JP5124806B2 (ja) * | 2006-06-27 | 2013-01-23 | 信越化学工業株式会社 | 光酸発生剤並びにこれを用いたレジスト材料及びパターン形成方法 |
| KR101442860B1 (ko) | 2006-09-08 | 2014-09-22 | 제이에스알 가부시끼가이샤 | 감방사선성 조성물 및 이것에 사용되는 저분자량 화합물의 제조 방법 |
| WO2008056795A1 (en) | 2006-11-10 | 2008-05-15 | Jsr Corporation | Polymerizable sulfonic acid onium salt and resin |
| DE102008006913A1 (de) * | 2007-01-25 | 2008-08-07 | Samsung Electronics Co., Ltd., Suwon | Photosäuregenerator, Photoresistzusammensetzung mit selbigem und Musterbildungsverfahren mit selbiger |
| CN101687781B (zh) | 2007-02-15 | 2015-08-12 | 中央硝子株式会社 | 光产酸剂用化合物以及使用它的抗蚀剂组合物、图案形成方法 |
| WO2009037981A1 (ja) | 2007-09-18 | 2009-03-26 | Central Glass Company, Limited | ２－（アルキルカルボニルオキシ）－１，１－ジフルオロエタンスルホン酸塩類およびその製造方法 |
| WO2009037980A1 (ja) | 2007-09-18 | 2009-03-26 | Central Glass Company, Limited | ２－ブロモ－２，２－ジフルオロエタノール及び２－（アルキルカルボニルオキシ）－１，１－ジフルオロエタンスルホン酸塩類の製造方法 |
-
2010
- 2010-03-11 JP JP2010054088A patent/JP5549288B2/ja active Active
- 2010-03-12 KR KR1020117023367A patent/KR20110123798A/ko not_active Ceased
- 2010-03-12 WO PCT/JP2010/054245 patent/WO2010104177A1/ja not_active Ceased
- 2010-03-12 US US13/254,708 patent/US8877960B2/en not_active Expired - Fee Related
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