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Metal-Catalyzed Addition Polymers for 157 nm Resist Applications. Synthesis and Polymerization of Partially Fluorinated, Ester-Functionalized Tricyclo[4.2.1.0_(2,5)]non-7-enes

Sanders, Daniel P. and Connor, Eric F. and Grubbs, Robert H. and Hung, Raymond J. and Osborn, Brian P. and Chiba, Takashi and MacDonald, Scott A. and Willson, C. Grant and Conley, Will (2003) Metal-Catalyzed Addition Polymers for 157 nm Resist Applications. Synthesis and Polymerization of Partially Fluorinated, Ester-Functionalized Tricyclo[4.2.1.0_(2,5)]non-7-enes. Macromolecules, 36 (5). pp. 1534-1542. ISSN 0024-9297. https://resolver.caltech.edu/CaltechAUTHORS:20170720-073409305

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Abstract

Fluorinated tricyclo[4.2.1.0^(2,5)]non-7-ene-3-carboxylic acid esters are shown to undergo metal-catalyzed addition polymerization. The resulting homopolymers are transparent at 157 nm and demonstrate the utility of these monomers in development of photoresists for 157 nm lithography. Fluorinated tricyclononene (TCN) structures with ester substituents exhibit up to 3 orders of magnitude more transparency at 157 nm than conventional ester-functionalized norbornene structures as determined by gas-phase vacuum-ultraviolet spectroscopy and variable angle spectroscopic ellipsometry. Unlike their fluorinated norbornene counterparts, the fluorinated, ester-functionalized TCN monomers successfully undergo transition-metal-catalyzed addition polymerization to produce polymers with high glass transition temperatures and the etch resistance required for photolithographic resist materials applications. The potential use of fluorinated TCN structures for 157 nm photoresists is demonstrated through the synthesis and characterization of TCN monomers and polymers.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ma021131iDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ma021131iPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ma021131iPublisherSupporting Information
ORCID:
AuthorORCID
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 2003 American Chemical Society. Received 16 July 2002. Published online 11 February 2003. Published in print 1 March 2003. The authors gratefully acknowledge the generous funding of the International SEMATECH and its member companies. D.P.S. especially acknowledges Dr. Todd R. Younkin, Dr. John P. Morgan, and Dr. Hoang V. Tran for helpful discussions. SEMATECH employee Danny Miller is acknowledged for help with the VASE measurements.
Funders:
Funding AgencyGrant Number
Sematech, Inc.UNSPECIFIED
Issue or Number:5
Record Number:CaltechAUTHORS:20170720-073409305
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170720-073409305
Official Citation:Metal-Catalyzed Addition Polymers for 157 nm Resist Applications. Synthesis and Polymerization of Partially Fluorinated, Ester-Functionalized Tricyclo[4.2.1.02,5]non-7-enes Daniel P. Sanders, Eric F. Connor, Robert H. Grubbs, Raymond J. Hung, Brian P. Osborn,T akashi Chiba, Scott A. MacDonald, C. Grant Willson, and Will Conley Macromolecules 2003 36 (5), 1534-1542 DOI: 10.1021/ma021131i
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:79229
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:20 Jul 2017 18:43
Last Modified:03 Oct 2019 18:17

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