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Polymers 2014, 6(2), 565-582; https://doi.org/10.3390/polym6020565

Synthesis of Narrow Molecular Weight Distribution Norbornene-Lactone Functionalized Polymers by Nitroxide-Mediated Polymerization: Candidates for 193-nm Photoresist Materials

1
Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany
2
Department of Chemical Engineering, McGill Institute of Advanced Materials (MIAM), Centre for Self-Assembled Chemical Structures (CSACS), McGill University, 3610 University Street, Montreal, QC H3A 0C5, Canada
*
Author to whom correspondence should be addressed.
Received: 16 January 2014 / Revised: 10 February 2014 / Accepted: 17 February 2014 / Published: 21 February 2014
(This article belongs to the Special Issue Controlled/Living Radical Polymerization)
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Abstract

One hundred ninety three-nanometer candidate photoresist materials were synthesized by nitroxide-mediated polymerization (NMP). Statistical copolymerizations of 5-methacryloyloxy-2,6-norboranecarbolactone (NLAM) with 5–10 mol% of controlling co-monomers (which are necessary for controlled polymerizations of methacrylates by NMP with the initiator used) in the feed, such as styrene (ST), p-acetoxystyrene (AcOST), 2-vinyl naphthalene (VN) and pentafluorostyrene (PFS), using the unimolecular BlocBuilder® initiator in 35 wt% dioxane solution at 90 °C were performed. As little as 5 mol% controlling comonomer in the feed was demonstrated to be sufficient to lead to linear evolution of number average molecular weight with respect to conversion up to 50%, and the resulting copolymers had dispersities of ~1.3 in most cases, an attractive feature for reducing line width roughness (LWR) in photoresists. The copolymers generally showed relatively low absorbance at 193 nm, comparable to other 193-nm candidate photoresists reported previously, despite the inclusion of a small amount of the styrenic co-monomers in the copolymer. View Full-Text
Keywords: nitroxide-mediated polymerization; copolymerization; 193-nm photoresists nitroxide-mediated polymerization; copolymerization; 193-nm photoresists
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Wang, Z.J.; Maric, M. Synthesis of Narrow Molecular Weight Distribution Norbornene-Lactone Functionalized Polymers by Nitroxide-Mediated Polymerization: Candidates for 193-nm Photoresist Materials. Polymers 2014, 6, 565-582.

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