Bis(fluoroalcohol) Monomers and Polymers: Improved Transparency Fluoropolymer Photoresists for Semiconductor Photolithography at 157 nm
Novel norbornene and [4.2.1.02,5]tricyclononene monomers bearing two hexafluoro-2-propanol substituents are polymerized with tetrafluoroethylene in solution, giving amorphous, largely alternating copolymers. The norbornene copolymer shows excellent transparency at 157 nm and a dissolution rate in aq...
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| Veröffentlicht in: | Macromolecules 2006-02, Vol.39 (4), p.1443-1448 |
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| container_title | Macromolecules |
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| creator | Feiring, Andrew E Crawford, Michael K Farnham, William B French, Roger H Leffew, Kenneth W Petrov, Viacheslav A Schadt, Frank L Tran, Hoang V Zumsteg, Fredrick C |
| description | Novel norbornene and [4.2.1.02,5]tricyclononene monomers bearing two hexafluoro-2-propanol substituents are polymerized with tetrafluoroethylene in solution, giving amorphous, largely alternating copolymers. The norbornene copolymer shows excellent transparency at 157 nm and a dissolution rate in aqueous tetramethylammonium hydroxide that is 100 000 times faster than the corresponding polymer with a single hexafluoro-2-propanol substituent on the norbornene ring. Intermediate dissolution rates are readily obtained using mixtures of the mono- and disubstituted norbornenes. The tricyclononene copolymer is obtained in higher conversion and molecular weight but has a higher absorbance at 157 nm and a slower dissolution rate. Partial protection of the fluoroalcohol groups as their methoxymethyl derivatives gives photoresist polymers with absorbance of 1.0 μm-1 or less which can be imaged at 157 nm using a photoacid generator. |
| doi_str_mv | 10.1021/ma051984l |
| format | Article |
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The norbornene copolymer shows excellent transparency at 157 nm and a dissolution rate in aqueous tetramethylammonium hydroxide that is 100 000 times faster than the corresponding polymer with a single hexafluoro-2-propanol substituent on the norbornene ring. Intermediate dissolution rates are readily obtained using mixtures of the mono- and disubstituted norbornenes. The tricyclononene copolymer is obtained in higher conversion and molecular weight but has a higher absorbance at 157 nm and a slower dissolution rate. Partial protection of the fluoroalcohol groups as their methoxymethyl derivatives gives photoresist polymers with absorbance of 1.0 μm-1 or less which can be imaged at 157 nm using a photoacid generator.</description><identifier>ISSN: 0024-9297</identifier><identifier>EISSN: 1520-5835</identifier><identifier>DOI: 10.1021/ma051984l</identifier><identifier>CODEN: MAMOBX</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Applied sciences ; Exact sciences and technology ; Organic polymers ; Physicochemistry of polymers ; Polymers with particular properties ; Preparation, kinetics, thermodynamics, mechanism and catalysts</subject><ispartof>Macromolecules, 2006-02, Vol.39 (4), p.1443-1448</ispartof><rights>Copyright © 2006 American Chemical Society</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a289t-2084d5e3e1e4148deb8037db5ff5ac91f167f981fb147baabee48acf37beb8483</citedby><cites>FETCH-LOGICAL-a289t-2084d5e3e1e4148deb8037db5ff5ac91f167f981fb147baabee48acf37beb8483</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ma051984l$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ma051984l$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56716,56766</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17727628$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Feiring, Andrew E</creatorcontrib><creatorcontrib>Crawford, Michael K</creatorcontrib><creatorcontrib>Farnham, William B</creatorcontrib><creatorcontrib>French, Roger H</creatorcontrib><creatorcontrib>Leffew, Kenneth W</creatorcontrib><creatorcontrib>Petrov, Viacheslav A</creatorcontrib><creatorcontrib>Schadt, Frank L</creatorcontrib><creatorcontrib>Tran, Hoang V</creatorcontrib><creatorcontrib>Zumsteg, Fredrick C</creatorcontrib><title>Bis(fluoroalcohol) Monomers and Polymers: Improved Transparency Fluoropolymer Photoresists for Semiconductor Photolithography at 157 nm</title><title>Macromolecules</title><addtitle>Macromolecules</addtitle><description>Novel norbornene and [4.2.1.02,5]tricyclononene monomers bearing two hexafluoro-2-propanol substituents are polymerized with tetrafluoroethylene in solution, giving amorphous, largely alternating copolymers. The norbornene copolymer shows excellent transparency at 157 nm and a dissolution rate in aqueous tetramethylammonium hydroxide that is 100 000 times faster than the corresponding polymer with a single hexafluoro-2-propanol substituent on the norbornene ring. Intermediate dissolution rates are readily obtained using mixtures of the mono- and disubstituted norbornenes. The tricyclononene copolymer is obtained in higher conversion and molecular weight but has a higher absorbance at 157 nm and a slower dissolution rate. Partial protection of the fluoroalcohol groups as their methoxymethyl derivatives gives photoresist polymers with absorbance of 1.0 μm-1 or less which can be imaged at 157 nm using a photoacid generator.</description><subject>Applied sciences</subject><subject>Exact sciences and technology</subject><subject>Organic polymers</subject><subject>Physicochemistry of polymers</subject><subject>Polymers with particular properties</subject><subject>Preparation, kinetics, thermodynamics, mechanism and catalysts</subject><issn>0024-9297</issn><issn>1520-5835</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><recordid>eNptkDFPwzAQhS0EEqUw8A-8IMEQsBO7dtigolCpiEqUObo4NkmVxJGdImVjhZ_JLyEliC5Mp7v73pPeQ-iUkktKQnpVAeE0lqzcQyPKQxJwGfF9NCIkZEEcxuIQHXm_JoRSzqIR-rwt_LkpN9ZZKJXNbXmBH21tK-08hjrDS1t22-X66_0Dz6vG2Ted4ZWD2jfgdK06PPuRNwOIl7ltrdO-8K3Hxjr8rKtC2TrbqP4-vMuize2rgybvMLSYcoHr6hgdGCi9PvmdY_Qyu1tNH4LF0_18erMIIJRxG4REsozrSFPNKJOZTiWJRJZyYziomBo6ESaW1KSUiRQg1ZpJUCYSaY8yGY3RxeCrnPXeaZM0rqjAdQklybbE5K_Enj0b2Aa8gtL0sVXhdwIhQjEJ5Y4D5ZO13bi6T_CP3ze-f4K2</recordid><startdate>20060221</startdate><enddate>20060221</enddate><creator>Feiring, Andrew E</creator><creator>Crawford, Michael K</creator><creator>Farnham, William B</creator><creator>French, Roger H</creator><creator>Leffew, Kenneth W</creator><creator>Petrov, Viacheslav A</creator><creator>Schadt, Frank L</creator><creator>Tran, Hoang V</creator><creator>Zumsteg, Fredrick C</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20060221</creationdate><title>Bis(fluoroalcohol) Monomers and Polymers: Improved Transparency Fluoropolymer Photoresists for Semiconductor Photolithography at 157 nm</title><author>Feiring, Andrew E ; Crawford, Michael K ; Farnham, William B ; French, Roger H ; Leffew, Kenneth W ; Petrov, Viacheslav A ; Schadt, Frank L ; Tran, Hoang V ; Zumsteg, Fredrick C</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a289t-2084d5e3e1e4148deb8037db5ff5ac91f167f981fb147baabee48acf37beb8483</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Applied sciences</topic><topic>Exact sciences and technology</topic><topic>Organic polymers</topic><topic>Physicochemistry of polymers</topic><topic>Polymers with particular properties</topic><topic>Preparation, kinetics, thermodynamics, mechanism and catalysts</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Feiring, Andrew E</creatorcontrib><creatorcontrib>Crawford, Michael K</creatorcontrib><creatorcontrib>Farnham, William B</creatorcontrib><creatorcontrib>French, Roger H</creatorcontrib><creatorcontrib>Leffew, Kenneth W</creatorcontrib><creatorcontrib>Petrov, Viacheslav A</creatorcontrib><creatorcontrib>Schadt, Frank L</creatorcontrib><creatorcontrib>Tran, Hoang V</creatorcontrib><creatorcontrib>Zumsteg, Fredrick C</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Macromolecules</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Feiring, Andrew E</au><au>Crawford, Michael K</au><au>Farnham, William B</au><au>French, Roger H</au><au>Leffew, Kenneth W</au><au>Petrov, Viacheslav A</au><au>Schadt, Frank L</au><au>Tran, Hoang V</au><au>Zumsteg, Fredrick C</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Bis(fluoroalcohol) Monomers and Polymers: Improved Transparency Fluoropolymer Photoresists for Semiconductor Photolithography at 157 nm</atitle><jtitle>Macromolecules</jtitle><addtitle>Macromolecules</addtitle><date>2006-02-21</date><risdate>2006</risdate><volume>39</volume><issue>4</issue><spage>1443</spage><epage>1448</epage><pages>1443-1448</pages><issn>0024-9297</issn><eissn>1520-5835</eissn><coden>MAMOBX</coden><abstract>Novel norbornene and [4.2.1.02,5]tricyclononene monomers bearing two hexafluoro-2-propanol substituents are polymerized with tetrafluoroethylene in solution, giving amorphous, largely alternating copolymers. 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| source | American Chemical Society Journals |
| subjects | Applied sciences Exact sciences and technology Organic polymers Physicochemistry of polymers Polymers with particular properties Preparation, kinetics, thermodynamics, mechanism and catalysts |
| title | Bis(fluoroalcohol) Monomers and Polymers: Improved Transparency Fluoropolymer Photoresists for Semiconductor Photolithography at 157 nm |
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