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Proceedings Paper

Development of optically transparent cyclic olefin photoresist binder resins
Author(s): Larry F. Rhodes; Chun Chang; Cheryl Burns; Dennis A. Barnes; Brian Bennett; Larry Seger; Xiaoming Wu; Andy Sobek; Mike Mishak; Craig Peterson; Leah Langsdorf; Hideo Hada; Hiroaki Shimizu; Kazuhito Sasaki
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Paper Abstract

Of all candidate 193 nm photoresist binder resins, transition metal catalyzed vinyl addition cyclic olefin (i.e., norbornene) polymers (PCO) hold the promise of high transparency and excellent etch resistance. In order to access lower molecular weight polymers, which are typically used in photoresists, α-olefin chain transfer agents (CTAs) are used in synthesizing vinyl addition poly(norbornenes). For example, HFANB (α,α-bis(trifluoromethyl)bicyclo [2.2.1]hept-5-ene-2-ethanol) homopolymers (p(HFANB)) with molecular weights (Mn) less than 5000 have been synthesized using such chain transfer agents. However, the optical density (OD) at 193 nm of these materials was found to rise as their molecular weights decreased consistent with a polymer end group effect. Extensive NMR and MS analysis of these polymers revealed that olefinic end groups derived from the chain transfer agent were responsible for the deleterious rise in OD. Chemical modification of these end groups by epoxidation, hydrogenation, hydrosilation, etc. lowers the OD of the polymer by removing the olefinic chromophore, however, it does require a second synthetic step. Thus a new class of non-olefinic chain transfer agents has been developed at Promerus that allow for excellent control of vinyl addition cyclic olefin polymer molecular weight and low optical density without the need of a post-polymerization chemical modification. Low molecular weight homopolymers of HFANB have been synthesized using these chain transfer agents that exhibit ODs ≤ 0.07 absorbance units per micron. This molecular weight control technology has been applied to both positive tone and negative tone vinyl addition cyclic olefin binder resins. Lithographic and etch performance of positive tone photoresists based on these binder resins will be presented.

Paper Details

Date Published: 4 May 2005
PDF: 13 pages
Proc. SPIE 5753, Advances in Resist Technology and Processing XXII, (4 May 2005); doi: 10.1117/12.600051
Show Author Affiliations
Larry F. Rhodes, Promerus LLC (United States)
Chun Chang, Promerus LLC (United States)
Cheryl Burns, Promerus LLC (United States)
Dennis A. Barnes, Promerus LLC (United States)
Brian Bennett, Promerus LLC (United States)
Larry Seger, Promerus LLC (United States)
Xiaoming Wu, Promerus LLC (United States)
Andy Sobek, Promerus LLC (United States)
Mike Mishak, Promerus LLC (United States)
Craig Peterson, Promerus LLC (United States)
Leah Langsdorf, Promerus LLC (United States)
Hideo Hada, Tokyo Ohka Kogyo Co., Ltd. (Japan)
Hiroaki Shimizu, Tokyo Ohka Kogyo Co., Ltd. (Japan)
Kazuhito Sasaki, Tokyo Ohka Kogyo Co., Ltd. (Japan)

Published in SPIE Proceedings Vol. 5753:
Advances in Resist Technology and Processing XXII
John L. Sturtevant, Editor(s)

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