Design of photoresists with reduced environmental impact. 1. Water-soluble resists based on photo-cross-linking of poly(vinyl alcohol)

Jennifer M. Havard, Sang Yeon Shim, Jean Frechet*, Qinghuang Lin, David R. Medeiros, C. Grant Willson, Jeffrey D. Byers

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

34 Scopus citations

Abstract

The feasibility of a chemically amplified fully water-soluble negative-tone resist based upon the cross-linking of a poly(vinyl alcohol) (PVA) matrix resin has been demonstrated. Two-component resists incorporating PVA and (2,4-dihydroxyphenyl)dimethylsulfonium triflate as a water-soluble photoacid generator were formulated in deionized water and spincoated onto bare silicon wafers. Negative-tone images were obtained upon irradiation at 254 nm, postbaking, and subsequent development in pure water. The two-component resist suffered from swelling during development, but improved performance was obtained through the addition of a cross-linking agent, hexamethoxymethylmelamine (HMMM). The resulting three-component, water-soluble resist was able to resolve micron-sized images using a 248 nm stepper, at a dose of ca. 200 mJ/cm2. Model studies conducted using 13C NMR monitoring with 2,4-pentanediol as a model for PVA showed that under acidic catalysis HMMM reacts to form active electrophilic species that add to the diol, affording ether linkages with concomitant liberation of methanol.

Original languageEnglish (US)
Pages (from-to)719-725
Number of pages7
JournalChemistry of Materials
Volume11
Issue number3
DOIs
StatePublished - Jan 1 1999

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Materials Chemistry

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