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 M.J. Fréchet; Qinghuang Lin; David R. Medeiros; C. Grant Willson; Jeffrey D. Byers

doi:10.1021/cm980603y

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 M.J. Fréchet^*, Qinghuang Lin, David R. Medeiros, C. Grant Willson, Jeffrey D. Byers

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

41 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 language	English (US)
Pages (from-to)	719-725
Number of pages	7
Journal	Chemistry of Materials
Volume	11
Issue number	3
DOIs	https://doi.org/10.1021/cm980603y
State	Published - 1999
Externally published	Yes

ASJC Scopus subject areas

General Chemistry
General Chemical Engineering
Materials Chemistry

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

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.",

author = "Havard, {Jennifer M.} and Shim, {Sang Yeon} and Fr{\'e}chet, {Jean M.J.} and Qinghuang Lin and Medeiros, {David R.} and {Grant Willson}, C. and Byers, {Jeffrey D.}",

year = "1999",

doi = "10.1021/cm980603y",

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AU - Havard, Jennifer M.

AU - Shim, Sang Yeon

AU - Fréchet, Jean M.J.

AU - Lin, Qinghuang

AU - Medeiros, David R.

AU - Grant Willson, C.

AU - Byers, Jeffrey D.

PY - 1999

Y1 - 1999

N2 - 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.

AB - 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.

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JF - Chemistry of Materials

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

Abstract

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