JP2010235601A5 - - Google Patents
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- Publication number
- JP2010235601A5 JP2010235601A5 JP2010054089A JP2010054089A JP2010235601A5 JP 2010235601 A5 JP2010235601 A5 JP 2010235601A5 JP 2010054089 A JP2010054089 A JP 2010054089A JP 2010054089 A JP2010054089 A JP 2010054089A JP 2010235601 A5 JP2010235601 A5 JP 2010235601A5
- Authority
- JP
- Japan
- Prior art keywords
- ion
- tri
- ammonium
- sec
- ammonium ions
- 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.)
- Granted
Links
- -1 ammonium ions Chemical class 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 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
- 239000000203 mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Chemical group 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- NURARYXRRMRHAX-UHFFFAOYSA-N n,n-diethylethanamine;1,1,2,2-tetrafluoro-4-hydroxybutane-1-sulfinic acid Chemical compound CC[NH+](CC)CC.OCCC(F)(F)C(F)(F)S([O-])=O NURARYXRRMRHAX-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000012925 reference material Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 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
- AFMJMJJTECHMQZ-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-4-hydroxybutane-1-sulfonate;triethylazanium Chemical compound CC[NH+](CC)CC.OCCC(F)(F)C(F)(F)S([O-])(=O)=O AFMJMJJTECHMQZ-UHFFFAOYSA-N 0.000 description 1
- BKZVDYBZILBKLF-UHFFFAOYSA-N 1,1-difluoro-2-(2-methylprop-2-enoyloxy)ethanesulfonate;triethylazanium Chemical compound CC[NH+](CC)CC.CC(=C)C(=O)OCC(F)(F)S([O-])(=O)=O BKZVDYBZILBKLF-UHFFFAOYSA-N 0.000 description 1
- 238000004293 19F NMR spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012046 mixed solvent 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
- 230000000704 physical effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000006351 sulfination reaction Methods 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
- VMJFYMAHEGJHFH-UHFFFAOYSA-M triphenylsulfanium;bromide Chemical compound [Br-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 VMJFYMAHEGJHFH-UHFFFAOYSA-M 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010054089A JP5549289B2 (ja) | 2009-03-13 | 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 |
| PCT/JP2010/054246 WO2010104178A1 (ja) | 2009-03-13 | 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 |
| US13/256,101 US9024058B2 (en) | 2009-03-13 | 2010-03-12 | Ammonium fluoroalkanesulfonates and a synthesis method therefor |
| KR1020117023807A KR20110126752A (ko) | 2009-03-13 | 2010-03-12 | 하이드록시플루오로알칸술핀산암모늄염의 제조 방법, 하이드록시플루오로알칸술폰산암모늄염의 제조 방법, 플루오로알칸술폰산오늄염의 제조 방법, 하이드록시플루오로알칸술핀산암모늄염 및 하이드록시플루오로알칸술폰산암모늄염 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009061240 | 2009-03-13 | ||
| JP2009061240 | 2009-03-13 | ||
| JP2010054089A JP5549289B2 (ja) | 2009-03-13 | 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 |
|---|---|
| JP2010235601A JP2010235601A (ja) | 2010-10-21 |
| JP2010235601A5 true JP2010235601A5 (enExample) | 2011-11-24 |
| JP5549289B2 JP5549289B2 (ja) | 2014-07-16 |
Family
ID=42728463
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010054089A Active JP5549289B2 (ja) | 2009-03-13 | 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) | US9024058B2 (enExample) |
| JP (1) | JP5549289B2 (enExample) |
| KR (1) | KR20110126752A (enExample) |
| WO (1) | WO2010104178A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3480508B2 (ja) | 1994-02-03 | 2003-12-22 | 株式会社岡部ロック | 箱製函装置 |
| TWI525066B (zh) * | 2011-04-13 | 2016-03-11 | 住友化學股份有限公司 | 鹽、光阻組成物及製備光阻圖案之方法 |
| JP6019849B2 (ja) * | 2011-09-08 | 2016-11-02 | セントラル硝子株式会社 | 含フッ素スルホン酸塩類、含フッ素スルホン酸塩樹脂、レジスト組成物及びそれを用いたパターン形成方法 |
| JP5615860B2 (ja) * | 2012-03-07 | 2014-10-29 | 信越化学工業株式会社 | 酸発生剤、化学増幅型レジスト材料、及びパターン形成方法 |
| JP6037689B2 (ja) * | 2012-07-10 | 2016-12-07 | 東京応化工業株式会社 | アンモニウム塩化合物の製造方法、及び酸発生剤の製造方法 |
| KR101723012B1 (ko) | 2016-04-29 | 2017-04-04 | 인하대학교 산학협력단 | 셀룰로오스 나노섬유를 포함하는 미세조류 응집제 및 이를 이용한 미세조류 회수 및 지질 함량 증대 방법 |
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 |
| TWI314250B (en) | 2002-02-19 | 2009-09-01 | Sumitomo Chemical Co | Positive resist composition |
| JP4103523B2 (ja) | 2002-09-27 | 2008-06-18 | Ｊｓｒ株式会社 | レジスト組成物 |
| JP4794835B2 (ja) * | 2004-08-03 | 2011-10-19 | 東京応化工業株式会社 | 高分子化合物、酸発生剤、ポジ型レジスト組成物、およびレジストパターン形成方法 |
| 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 |
| TWI332122B (en) | 2005-04-06 | 2010-10-21 | Shinetsu Chemical Co | Novel sulfonate salts and derivatives, photoacid generators, resist compositions and patterning process |
| JP5428159B2 (ja) | 2005-05-11 | 2014-02-26 | Ｊｓｒ株式会社 | 新規化合物および重合体、ならびに感放射線性樹脂組成物 |
| 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 |
| 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 |
| EP2060949A4 (en) * | 2006-09-08 | 2011-05-04 | Jsr Corp | RADIATION-SENSITIVE COMPOSITION AND PROCESS FOR PRODUCING A LOW-MOLECULAR COMPOUND FOR USE THEREIN |
| WO2008056795A1 (en) | 2006-11-10 | 2008-05-15 | Jsr Corporation | Polymerizable sulfonic acid onium salt and resin |
| JP5401800B2 (ja) | 2007-02-15 | 2014-01-29 | セントラル硝子株式会社 | 光酸発生剤用化合物及びそれを用いたレジスト組成物、パターン形成方法 |
| TWI438182B (zh) * | 2007-07-25 | 2014-05-21 | Sumitomo Chemical Co | 適用於酸產生劑之鹽以及含有該鹽之化學放大正型抗蝕劑組成物 |
-
2010
- 2010-03-11 JP JP2010054089A patent/JP5549289B2/ja active Active
- 2010-03-12 WO PCT/JP2010/054246 patent/WO2010104178A1/ja not_active Ceased
- 2010-03-12 KR KR1020117023807A patent/KR20110126752A/ko not_active Ceased
- 2010-03-12 US US13/256,101 patent/US9024058B2/en active Active
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