JP2008501779A5 - - Google Patents
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- Publication number
- JP2008501779A5 JP2008501779A5 JP2007526597A JP2007526597A JP2008501779A5 JP 2008501779 A5 JP2008501779 A5 JP 2008501779A5 JP 2007526597 A JP2007526597 A JP 2007526597A JP 2007526597 A JP2007526597 A JP 2007526597A JP 2008501779 A5 JP2008501779 A5 JP 2008501779A5
- Authority
- JP
- Japan
- Prior art keywords
- methacrylate
- adamantyl
- gamma
- poly
- butyrolactone
- 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.)
- Pending
Links
- -1 cyclic olefin Chemical class 0.000 description 22
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- LJZJMIZQMNDARW-UHFFFAOYSA-N decan-3-yl 2-methylprop-2-enoate Chemical compound CCCCCCCC(CC)OC(=O)C(C)=C LJZJMIZQMNDARW-UHFFFAOYSA-N 0.000 description 5
- 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 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- FYGUSUBEMUKACF-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-5-carboxylic acid Chemical compound C1C2C(C(=O)O)CC1C=C2 FYGUSUBEMUKACF-UHFFFAOYSA-N 0.000 description 4
- CIKZJZIPTDPBCW-UHFFFAOYSA-N tert-butyl bicyclo[2.2.1]hept-2-ene-4-carboxylate Chemical compound C1CC2C=CC1(C(=O)OC(C)(C)C)C2 CIKZJZIPTDPBCW-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DCTVCFJTKSQXED-UHFFFAOYSA-N (2-ethyl-2-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC1C(CC)(OC(=O)C(C)=C)C2C3 DCTVCFJTKSQXED-UHFFFAOYSA-N 0.000 description 2
- YRPLSAWATHBYFB-UHFFFAOYSA-N (2-methyl-2-adamantyl) prop-2-enoate Chemical compound C1C(C2)CC3CC1C(C)(OC(=O)C=C)C2C3 YRPLSAWATHBYFB-UHFFFAOYSA-N 0.000 description 2
- DKDKCSYKDZNMMA-UHFFFAOYSA-N (3-hydroxy-1-adamantyl) prop-2-enoate Chemical compound C1C(C2)CC3CC1(O)CC2(OC(=O)C=C)C3 DKDKCSYKDZNMMA-UHFFFAOYSA-N 0.000 description 2
- CEZCTKYAEUCICK-UHFFFAOYSA-N 2-ethylundec-7-enoic acid Chemical compound CCCC=CCCCCC(CC)C(O)=O CEZCTKYAEUCICK-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- JYVXNLLUYHCIIH-UHFFFAOYSA-N (+/-)-mevalonolactone Natural products CC1(O)CCOC(=O)C1 JYVXNLLUYHCIIH-UHFFFAOYSA-N 0.000 description 1
- QSUJHKWXLIQKEY-UHFFFAOYSA-N (2-oxooxolan-3-yl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCOC1=O QSUJHKWXLIQKEY-UHFFFAOYSA-N 0.000 description 1
- HFLCKUMNXPOLSN-UHFFFAOYSA-N (3,5-dihydroxy-1-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3(O)CC2(O)CC1(OC(=O)C(=C)C)C3 HFLCKUMNXPOLSN-UHFFFAOYSA-N 0.000 description 1
- OOIBFPKQHULHSQ-UHFFFAOYSA-N (3-hydroxy-1-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC2(O)CC1(OC(=O)C(=C)C)C3 OOIBFPKQHULHSQ-UHFFFAOYSA-N 0.000 description 1
- MQPLRNXGZXAKDQ-UHFFFAOYSA-N (3-hydroxy-5,7-dimethyl-1-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)(C)CC3(C)CC2(O)CC1(OC(=O)C(=C)C)C3 MQPLRNXGZXAKDQ-UHFFFAOYSA-N 0.000 description 1
- ZROFAXCQYPKWCY-UHFFFAOYSA-N (5-oxooxolan-3-yl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1COC(=O)C1 ZROFAXCQYPKWCY-UHFFFAOYSA-N 0.000 description 1
- DGPNNZGZXFUKKC-UHFFFAOYSA-N 2-cyclopentylpent-2-enoic acid Chemical compound CCC=C(C(O)=O)C1CCCC1 DGPNNZGZXFUKKC-UHFFFAOYSA-N 0.000 description 1
- AKGGHYOWZFPMTM-UHFFFAOYSA-N 4-bicyclo[2.2.1]heptanyl 2-methylprop-2-enoate;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.C1CC2CCC1(OC(=O)C(=C)C)C2 AKGGHYOWZFPMTM-UHFFFAOYSA-N 0.000 description 1
- 101100452478 Arabidopsis thaliana DHAD gene Proteins 0.000 description 1
- JYVXNLLUYHCIIH-ZCFIWIBFSA-N R-mevalonolactone, (-)- Chemical compound C[C@@]1(O)CCOC(=O)C1 JYVXNLLUYHCIIH-ZCFIWIBFSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- VSSAKJGDGOOSHH-UHFFFAOYSA-M lithium 1,1,2,2,3,3,4,4-octafluoro-4-(1,2,2,2-tetrafluoroethoxy)butane-1-sulfonate Chemical compound [Li+].C(C(F)(F)F)(OC(C(C(C(F)(F)S(=O)(=O)[O-])(F)F)(F)F)(F)F)F VSSAKJGDGOOSHH-UHFFFAOYSA-M 0.000 description 1
- 229940057061 mevalonolactone Drugs 0.000 description 1
- KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/863,042 US20050271974A1 (en) | 2004-06-08 | 2004-06-08 | Photoactive compounds |
| PCT/IB2005/001923 WO2005121894A2 (en) | 2004-06-08 | 2005-06-08 | Photoactive compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008501779A JP2008501779A (ja) | 2008-01-24 |
| JP2008501779A5 true JP2008501779A5 (enExample) | 2008-06-19 |
Family
ID=35044987
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007526597A Pending JP2008501779A (ja) | 2004-06-08 | 2005-06-08 | 光活性化合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20050271974A1 (enExample) |
| EP (1) | EP1766474A2 (enExample) |
| JP (1) | JP2008501779A (enExample) |
| KR (1) | KR20070030200A (enExample) |
| CN (1) | CN1961260A (enExample) |
| TW (1) | TW200613256A (enExample) |
| WO (1) | WO2005121894A2 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050214674A1 (en) | 2004-03-25 | 2005-09-29 | Yu Sui | Positive-working photoimageable bottom antireflective coating |
| US7255970B2 (en) * | 2005-07-12 | 2007-08-14 | Az Electronic Materials Usa Corp. | Photoresist composition for imaging thick films |
| JP4695941B2 (ja) * | 2005-08-19 | 2011-06-08 | 富士フイルム株式会社 | 液浸露光用ポジ型レジスト組成物及びそれを用いたパターン形成方法 |
| US20070105040A1 (en) * | 2005-11-10 | 2007-05-10 | Toukhy Medhat A | Developable undercoating composition for thick photoresist layers |
| US7601482B2 (en) * | 2006-03-28 | 2009-10-13 | Az Electronic Materials Usa Corp. | Negative photoresist compositions |
| JP4881692B2 (ja) * | 2006-10-23 | 2012-02-22 | 富士フイルム株式会社 | 感光性組成物、該感光性組成物に用いられる化合物及び該感光性組成物を用いたパターン形成方法 |
| US20080171270A1 (en) * | 2007-01-16 | 2008-07-17 | Munirathna Padmanaban | Polymers Useful in Photoresist Compositions and Compositions Thereof |
| JP5364256B2 (ja) * | 2007-06-13 | 2013-12-11 | 東京応化工業株式会社 | 化合物、酸発生剤、レジスト組成物およびレジストパターン形成方法 |
| CN101778818B (zh) * | 2007-08-07 | 2014-01-08 | 株式会社Adeka | 芳香族硫鎓盐化合物 |
| US8252503B2 (en) * | 2007-08-24 | 2012-08-28 | Az Electronic Materials Usa Corp. | Photoresist compositions |
| US8088548B2 (en) * | 2007-10-23 | 2012-01-03 | Az Electronic Materials Usa Corp. | Bottom antireflective coating compositions |
| US8455176B2 (en) | 2008-11-12 | 2013-06-04 | Az Electronic Materials Usa Corp. | Coating composition |
| US8632948B2 (en) | 2009-09-30 | 2014-01-21 | Az Electronic Materials Usa Corp. | Positive-working photoimageable bottom antireflective coating |
| US20110086312A1 (en) * | 2009-10-09 | 2011-04-14 | Dammel Ralph R | Positive-Working Photoimageable Bottom Antireflective Coating |
| US9012126B2 (en) | 2012-06-15 | 2015-04-21 | Az Electronic Materials (Luxembourg) S.A.R.L. | Positive photosensitive material |
| US8906594B2 (en) | 2012-06-15 | 2014-12-09 | Az Electronic Materials (Luxembourg) S.A.R.L. | Negative-working thick film photoresist |
| JP5830503B2 (ja) * | 2012-09-15 | 2015-12-09 | 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 | 酸発生剤化合物およびそれを含むフォトレジスト |
| WO2014175275A1 (ja) * | 2013-04-23 | 2014-10-30 | 三菱瓦斯化学株式会社 | 新規脂環式エステル化合物、（メタ）アクリル共重合体およびそれを含む感光性樹脂組成物 |
| JP6442271B2 (ja) * | 2014-12-22 | 2018-12-19 | デクセリアルズ株式会社 | 化合物、熱硬化性樹脂組成物、及び熱硬化性シート |
| TWI731961B (zh) | 2016-04-19 | 2021-07-01 | 德商馬克專利公司 | 正向感光材料及形成正向凸紋影像之方法 |
| JP6782569B2 (ja) * | 2016-06-28 | 2020-11-11 | 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 |
| KR102261808B1 (ko) | 2016-08-09 | 2021-06-07 | 리지필드 액퀴지션 | 환경적으로 안정한 후막성 화학증폭형 레지스트 |
| SG11202100517VA (en) | 2018-09-05 | 2021-02-25 | Merck Patent Gmbh | Positive working photosensitive material |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5021197A (en) * | 1988-06-16 | 1991-06-04 | Mitsubishi Gas Chemical Company, Inc. | Process for production of sulfonium compounds |
| DE3902114A1 (de) * | 1989-01-25 | 1990-08-02 | Basf Ag | Strahlungsempfindliche, ethylenisch ungesaettigte, copolymerisierbare sulfoniumsalze und verfahren zu deren herstellung |
| US5075476A (en) * | 1989-06-07 | 1991-12-24 | Mitsubishi Gas Chemical Company, Inc. | Process for production of sulfonium compounds and novel methylthiphenol derivatives |
| US5252436A (en) * | 1989-12-15 | 1993-10-12 | Basf Aktiengesellschaft | Process for developing a positive-working photoresist containing poly(p-hydroxystyrene) and sulfonium salt with an aqueous developer containing basic organic compounds |
| US5274148A (en) * | 1992-08-10 | 1993-12-28 | Isp Investments, Inc. | Dialky alkoxy phenyl sulfonium salt cationic initiators |
| EP0751124B1 (en) * | 1994-03-09 | 2000-12-13 | Nippon Soda Co., Ltd. | Sulfonium salt compound and polymerization initiator |
| JP2770740B2 (ja) * | 1994-07-14 | 1998-07-02 | 日本電気株式会社 | 橋かけ環式アルキル基を有するスルホニウム塩化合物および光酸発生剤 |
| DE846681T1 (de) * | 1995-08-22 | 1998-11-19 | Nippon Soda Co. Ltd., Tokio/Tokyo | Neue sulfoniumsalzverbindungen, polymerisierungsinitiator, härtbare zusammensetzung und stärkungsverfahren |
| JP3587325B2 (ja) * | 1996-03-08 | 2004-11-10 | 富士写真フイルム株式会社 | ポジ型感光性組成物 |
| US5693903A (en) * | 1996-04-04 | 1997-12-02 | Coda Music Technology, Inc. | Apparatus and method for analyzing vocal audio data to provide accompaniment to a vocalist |
| JP4226803B2 (ja) * | 2000-08-08 | 2009-02-18 | 富士フイルム株式会社 | ポジ型感光性組成物 |
| EP1179750B1 (en) * | 2000-08-08 | 2012-07-25 | FUJIFILM Corporation | Positive photosensitive composition and method for producing a precision integrated circuit element using the same |
| 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 |
| US6749987B2 (en) * | 2000-10-20 | 2004-06-15 | Fuji Photo Film Co., Ltd. | Positive photosensitive composition |
| JP2004519520A (ja) * | 2001-04-05 | 2004-07-02 | アーチ・スペシャルティ・ケミカルズ・インコーポレイテッド | フォトレジストのためのパーフルオロアルキルスルフォン酸化合物 |
| JP4054978B2 (ja) * | 2001-08-24 | 2008-03-05 | 信越化学工業株式会社 | レジスト材料及びパターン形成方法 |
| US7105267B2 (en) * | 2001-08-24 | 2006-09-12 | Shin-Etsu Chemical Co., Ltd. | Resist compositions and patterning process |
| JP2003228167A (ja) * | 2002-02-01 | 2003-08-15 | Fuji Photo Film Co Ltd | ネガ型レジスト組成物 |
| JP3841399B2 (ja) * | 2002-02-21 | 2006-11-01 | 富士写真フイルム株式会社 | ポジ型レジスト組成物 |
| US7214467B2 (en) * | 2002-06-07 | 2007-05-08 | Fujifilm Corporation | Photosensitive resin composition |
| US20030235775A1 (en) * | 2002-06-13 | 2003-12-25 | Munirathna Padmanaban | Photoresist composition for deep ultraviolet lithography comprising a mixture of photoactive compounds |
| US6841333B2 (en) * | 2002-11-01 | 2005-01-11 | 3M Innovative Properties Company | Ionic photoacid generators with segmented hydrocarbon-fluorocarbon sulfonate anions |
| US7358408B2 (en) * | 2003-05-16 | 2008-04-15 | Az Electronic Materials Usa Corp. | Photoactive compounds |
-
2004
- 2004-06-08 US US10/863,042 patent/US20050271974A1/en not_active Abandoned
-
2005
- 2005-05-26 TW TW094117283A patent/TW200613256A/zh unknown
- 2005-06-08 KR KR1020067024474A patent/KR20070030200A/ko not_active Withdrawn
- 2005-06-08 JP JP2007526597A patent/JP2008501779A/ja active Pending
- 2005-06-08 CN CNA2005800173866A patent/CN1961260A/zh active Pending
- 2005-06-08 WO PCT/IB2005/001923 patent/WO2005121894A2/en not_active Ceased
- 2005-06-08 EP EP05756699A patent/EP1766474A2/en not_active Withdrawn
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