JP2011028270A5 - - Google Patents
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- Publication number
- JP2011028270A5 JP2011028270A5 JP2010163887A JP2010163887A JP2011028270A5 JP 2011028270 A5 JP2011028270 A5 JP 2011028270A5 JP 2010163887 A JP2010163887 A JP 2010163887A JP 2010163887 A JP2010163887 A JP 2010163887A JP 2011028270 A5 JP2011028270 A5 JP 2011028270A5
- Authority
- JP
- Japan
- Prior art keywords
- calix
- resorcinarene
- unprotected
- fully protected
- alkyl
- 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
- 239000000203 mixture Substances 0.000 claims description 22
- 229920002120 photoresistant polymer Polymers 0.000 claims description 21
- -1 sensitizers Substances 0.000 claims description 21
- 238000004090 dissolution Methods 0.000 claims description 9
- YVGKLVZOQWYWTI-UHFFFAOYSA-N calixresorc[4]arene Chemical compound C1C(C(=CC=2O)O)=CC=2CC(C(=CC=2O)O)=CC=2CC(=C2)C(O)=CC(O)=C2CC2=CC1=C(O)C=C2O YVGKLVZOQWYWTI-UHFFFAOYSA-N 0.000 claims 30
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 238000000034 method Methods 0.000 claims 11
- 239000002253 acid Substances 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- 239000011248 coating agent Substances 0.000 claims 3
- 238000000576 coating method Methods 0.000 claims 3
- 230000001012 protector Effects 0.000 claims 3
- 230000005855 radiation Effects 0.000 claims 3
- 239000002318 adhesion promoter Substances 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 150000007942 carboxylates Chemical class 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 238000009792 diffusion process Methods 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 150000002367 halogens Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- 239000003607 modifier Substances 0.000 claims 2
- 239000000049 pigment Substances 0.000 claims 2
- 239000004014 plasticizer Substances 0.000 claims 2
- 239000003755 preservative agent Substances 0.000 claims 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 239000000758 substrate Substances 0.000 claims 2
- 238000010894 electron beam technology Methods 0.000 claims 1
- 230000002335 preservative effect Effects 0.000 claims 1
- 239000011521 glass Substances 0.000 description 24
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 20
- 238000001878 scanning electron micrograph Methods 0.000 description 8
- VTJUKNSKBAOEHE-UHFFFAOYSA-N calixarene Chemical compound COC(=O)COC1=C(CC=2C(=C(CC=3C(=C(C4)C=C(C=3)C(C)(C)C)OCC(=O)OC)C=C(C=2)C(C)(C)C)OCC(=O)OC)C=C(C(C)(C)C)C=C1CC1=C(OCC(=O)OC)C4=CC(C(C)(C)C)=C1 VTJUKNSKBAOEHE-UHFFFAOYSA-N 0.000 description 6
- 238000005286 illumination Methods 0.000 description 3
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/507,968 US7993812B2 (en) | 2009-07-23 | 2009-07-23 | Calixarene blended molecular glass photoresists and processes of use |
| US12/507968 | 2009-07-23 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011028270A JP2011028270A (ja) | 2011-02-10 |
| JP2011028270A5 true JP2011028270A5 (enExample) | 2013-10-10 |
| JP5385870B2 JP5385870B2 (ja) | 2014-01-08 |
Family
ID=43497606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010163887A Expired - Fee Related JP5385870B2 (ja) | 2009-07-23 | 2010-07-21 | カリックスアレーン・ブレンド分子ガラス・フォトレジスト及び使用のプロセス |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US7993812B2 (enExample) |
| JP (1) | JP5385870B2 (enExample) |
| KR (1) | KR20110010056A (enExample) |
| CN (1) | CN101963758B (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102597034A (zh) * | 2009-08-31 | 2012-07-18 | 三菱瓦斯化学株式会社 | 环状化合物、其制造方法、辐射敏感组合物及抗蚀图案形成方法 |
| CN102596874A (zh) * | 2009-09-09 | 2012-07-18 | 三菱瓦斯化学株式会社 | 环状化合物、其制造方法、辐射敏感组合物及抗蚀图案形成方法 |
| EP2487148B1 (en) * | 2009-10-06 | 2014-12-31 | Mitsubishi Gas Chemical Company, Inc. | Cyclic compound, method for producing same, radiation sensitive composition, and method for forming resist pattern |
| CN102666461B (zh) * | 2009-11-27 | 2015-09-30 | 三菱瓦斯化学株式会社 | 环状化合物、其生产方法、放射线敏感性组合物和抗蚀图案形成方法 |
| JP5692090B2 (ja) * | 2009-12-07 | 2015-04-01 | 三菱瓦斯化学株式会社 | 低分子量ポジ型感放射線性組成物及びレジストパターン形成方法 |
| JP2011180579A (ja) * | 2010-02-04 | 2011-09-15 | Sumitomo Chemical Co Ltd | レジスト組成物 |
| JPWO2012032790A1 (ja) * | 2010-09-10 | 2014-01-20 | 出光興産株式会社 | 酸解離性溶解抑止基を有する組成物 |
| JP2013067612A (ja) * | 2011-09-23 | 2013-04-18 | Rohm & Haas Electronic Materials Llc | カリックスアレーン化合物およびこれを含むフォトレジスト組成物 |
| JP2013079230A (ja) * | 2011-09-23 | 2013-05-02 | Rohm & Haas Electronic Materials Llc | カリックスアレーンおよびこれを含むフォトレジスト組成物 |
| CN102557930B (zh) * | 2012-01-05 | 2014-01-29 | 南京航空航天大学 | 联苯型分子玻璃及其制备方法 |
| JP5798964B2 (ja) * | 2012-03-27 | 2015-10-21 | 富士フイルム株式会社 | パターン形成方法、及び、これらを用いる電子デバイスの製造方法 |
| GB2501681A (en) * | 2012-04-30 | 2013-11-06 | Ibm | Nanoimprint lithographic methods |
| JP6268677B2 (ja) | 2012-10-17 | 2018-01-31 | 三菱瓦斯化学株式会社 | レジスト組成物 |
| US9063420B2 (en) * | 2013-07-16 | 2015-06-23 | Rohm And Haas Electronic Materials Llc | Photoresist composition, coated substrate, and method of forming electronic device |
| CN103752208A (zh) * | 2014-01-28 | 2014-04-30 | 扬州大学 | 一种起泡剂和稳泡剂及其合成方法 |
| CN108897192B (zh) * | 2018-04-19 | 2022-04-05 | 中科院广州化学有限公司南雄材料生产基地 | 一种巯基-烯纳米压印光刻胶及其使用方法 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5143784A (en) | 1990-05-10 | 1992-09-01 | Nec Corporation | Soluble calixarene derivative and films thereof |
| JP3443466B2 (ja) * | 1993-10-28 | 2003-09-02 | シップレーカンパニー エル エル シー | 感光性樹脂組成物 |
| JP3116751B2 (ja) | 1993-12-03 | 2000-12-11 | ジェイエスアール株式会社 | 感放射線性樹脂組成物 |
| JP3486341B2 (ja) | 1997-09-18 | 2004-01-13 | 株式会社東芝 | 感光性組成物およびそれを用いたパターン形成法 |
| US6093517A (en) * | 1998-07-31 | 2000-07-25 | International Business Machines Corporation | Calixarenes for use as dissolution inhibitors in lithographic photoresist compositions |
| US7037638B1 (en) | 2000-05-31 | 2006-05-02 | International Business Machines Corporation | High sensitivity crosslinkable photoresist composition, based on soluble, film forming dendrimeric calix[4] arene compositions method and for use thereof |
| US6713225B2 (en) | 2002-03-15 | 2004-03-30 | Toyo Gosei Kogyo Co., Ltd. | 1,2-Naphthoquinone-2-diazidesulfonate ester photosensitive agent, method for producing the photosensitive agent, and photoresist composition |
| JP4076789B2 (ja) * | 2002-05-09 | 2008-04-16 | Ｊｓｒ株式会社 | カリックスレゾルシンアレーン誘導体および感放射線性樹脂組成物 |
| CN1688939A (zh) * | 2002-10-15 | 2005-10-26 | 出光兴产株式会社 | 光致抗蚀剂基材及其精制方法、和光致抗蚀剂组合物 |
| US7141692B2 (en) | 2003-11-24 | 2006-11-28 | International Business Machines Corporation | Molecular photoresists containing nonpolymeric silsesquioxanes |
| TWI342873B (en) | 2004-02-04 | 2011-06-01 | Univ Kanagawa | Calixarene compound, method for menufacturing same, intermediate of same, and composition containing same |
| CN101650531A (zh) * | 2004-04-05 | 2010-02-17 | 出光兴产株式会社 | 间苯二酚杯芳烃化合物、光致抗蚀剂基材及其组合物 |
| JPWO2005097725A1 (ja) | 2004-04-05 | 2008-02-28 | 出光興産株式会社 | カリックスレゾルシナレン化合物、フォトレジスト基材及びその組成物 |
| JP5092238B2 (ja) * | 2004-12-24 | 2012-12-05 | 三菱瓦斯化学株式会社 | レジスト用化合物および感放射線性組成物 |
| JP4434985B2 (ja) | 2005-02-18 | 2010-03-17 | 信越化学工業株式会社 | レジスト材料並びにこれを用いたパターン形成方法 |
| CN101218202A (zh) * | 2005-06-01 | 2008-07-09 | 木下博雄 | 杯间苯二酚芳烃化合物以及由其构成的光致抗蚀剂基材及其组合物 |
| KR100707163B1 (ko) * | 2005-10-12 | 2007-04-13 | 삼성에스디아이 주식회사 | 고체산, 이를 포함하는 고분자 전해질막 및 이를 채용한연료전지 |
| US20070122734A1 (en) | 2005-11-14 | 2007-05-31 | Roberts Jeanette M | Molecular photoresist |
| US8092976B2 (en) | 2006-09-28 | 2012-01-10 | Fujifilm Corporation | Resist composition and pattern forming method using the same |
| WO2008136372A1 (ja) * | 2007-04-27 | 2008-11-13 | Idemitsu Kosan Co., Ltd. | フォトレジスト基材、及びそれを含んでなるフォトレジスト組成物 |
| JP5435995B2 (ja) * | 2009-01-30 | 2014-03-05 | 出光興産株式会社 | 環状化合物の製造方法 |
-
2009
- 2009-07-23 US US12/507,968 patent/US7993812B2/en not_active Expired - Fee Related
-
2010
- 2010-07-08 KR KR1020100065657A patent/KR20110010056A/ko not_active Ceased
- 2010-07-21 JP JP2010163887A patent/JP5385870B2/ja not_active Expired - Fee Related
- 2010-07-23 CN CN2010102378473A patent/CN101963758B/zh not_active Expired - Fee Related
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