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Resist materials for 157-nm microlithography: an update

Hung, Raymond J. and Tran, Hoang V. and Trinque, Brian C. and Chiba, Takashi and Yamada, Shintaro and Sanders, Daniel P. and Connor, Eric F. and Grubbs, Robert H. and Klopp, John and Frechet, Jean M. J. and Thomas, Brian H. and Shafer, Gregory J. and DesMarteau, Darryl D. and Conley, Will and Willson, C. Grant (2001) Resist materials for 157-nm microlithography: an update. In: Advances in Resist Technology and Processing XVIII. Proceedings of SPIE. No.4345. Society of Photo-optical Instrumentation Engineers (SPIE) , Bellingham, WA, pp. 385-395. ISBN 9780819440310. https://resolver.caltech.edu/CaltechAUTHORS:20181213-143629856

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Abstract

Fluorocarbon polymers and siloxane-based polymers have been identified as promising resist candidates for 157 nm material design because of their relatively high transparency at this wavelength. This paper reports our recent progress toward developing 157 nm resist materials based on the first of these two polymer systems. In addition to the 2-hydroxyhexafluoropropyl group, (alpha) -trifluoromethyl carboxylic acids have been identified as surprisingly transparent acidic functional groups. Polymers based on these groups have been prepared and preliminary imaging studies at 157 nm are described. 2-Trifluoromethyl-bicyclo[2,2,1] heptane-2-carboxylic acid methyl ester derived from methyl 2-(trifluoromethyl)acrylate was also prepared and gas-phase VUV measurements showed substantially improved transparency over norbornane. This appears to be a general characteristic of norbornane-bearing geminal electron-withdrawing substituents on the 2 carbon bridge. Unfortunately, neither the NiII nor PdII catalysts polymerize these transparent norbornene monomers by vinyl addition. However, several new approaches to incorporating these transparent monomers into functional polymers have been investigated. The first involved the synthesis of tricyclononene (TCN) monomers that move the bulky electron withdrawing groups further away from the site of addition. The hydrogenated geminally substituted TCN monomer still has far better transparency at 157 nm than norbornane. The second approach involved copolymerizing the norbornene monomers with carbon monoxide. The third approach involved free-radical polymerization of norbornene monomers with tetrafluoroethylene and/or other electron-deficient comonomers. All these approaches provided new materials with encouraging absorbance at 157 nm. The lithographic performance of some of these polymers is discussed.


Item Type:Book Section
Related URLs:
URLURL TypeDescription
https://doi.org/10.1117/12.436870DOIArticle
ORCID:
AuthorORCID
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 2001 Society of Photo-Optical Instrumentation Engineers (SPIE). The authors gratefully acknowledge International SEMATECH for financial support of this work. Dr. Ralph Dammel from AZ Clariant and Central Glass Co. are also acknowledged for their generous donation of key monomers. We are indebted to JSR Corporation for support of Mr. Chiba, Shipley Co. for support of Dr. Yamada and ITRI for support of Dr. Vincent Jean. We are also indebted to Danny Miller and DC Owe-Yang from SEMATECH for their imaging work. Matthew Pinnow, Brian Osborn, and Colin Brodsky are gratefully acknowledged for their contributions to monomer synthesis and VUV measurements. Dr. Scott MacDonald is thanked for his helpful insights. Finally, we acknowledge the help of our undergraduates Anthony Vander Heyden and Jennifer Wunderlich.
Funders:
Funding AgencyGrant Number
Sematech, Inc.UNSPECIFIED
JSR CorporationUNSPECIFIED
Shipley Co.UNSPECIFIED
Industrial Technology Research InstituteUNSPECIFIED
Subject Keywords:157 nm lithography, 157 nm resist, 2-(trifluoromethyl)acrylates, fluoronorbornanes, metal-catalyzed addition polymerization, carbon monoxide copolymerization, dissolution inhibitor
Series Name:Proceedings of SPIE
Issue or Number:4345
Record Number:CaltechAUTHORS:20181213-143629856
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20181213-143629856
Official Citation:Raymond Jui-Pu Hung, Hoang Vi Tran, Brian C. Trinque, Takashi Chiba, Shintaro Yamada, Daniel Sanders, Eric F Connor, Robert H. Grubbs, John M. Klopp, Jean M. J. Frechet, Brian H. Thomas, Gregory John Shafer, Darryl D DesMarteau, Will Conley, C. Grant Willson, "Resist materials for 157-nm microlithography: an update," Proc. SPIE 4345, Advances in Resist Technology and Processing XVIII, (24 August 2001); doi: 10.1117/12.436870
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:91785
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:19 Dec 2018 23:00
Last Modified:03 Oct 2019 20:38

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