A new photoresist material for 157 nm lithography-2

T. Fujigaya, S. Ando, Y. Shibasaki, S. Kishimura, M. Endo, M. Sasago, M. Ueda

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Time-dependent density functional theory (TD-DFT) calculations using the B3LYP hybrid functional suggested that sulfonic acid esters are transparent at around 157 nm region. Based on these findings, poly(methyl vinyl sulfonate) [poly(VSO3Me)] was prepared and found to have an extremely low absorbance (Abs.) of 2.2 μm-1 at 157 nm. Various alkyl vinyl sulfonates (VSO3R)s were prepared from 2-chloroethanesulfonyl chloride and alcohol components in the presence of pyridine, and their radical polymerizations were conducted in bulk using 2,2′-azobis(isobutyronitrile) as an initiator. Polymerizations of primary and secondary VSO3Rs bearing small alkyl substituents gave homopolymers with high molecular weights. Among them, the Abs. of poly(2,2,2-trifluoroethyl vinyl sulfonate) reached to 1.3 μm-1. Various copolymers from alkyl vinyl sulfonates and 4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropyl)styrene (HFISt) were also prepared and the Abs. of poly(1,1,1,3,3,3-hexafluoroisopropyl vinyl sulfonate40-co-HFISt60) [poly(VSO3iPr6F40-co-HFISt60)] was found to be 2.4 μm-1 at 157 nm. The photoresist consisting of partially t-BOC-protected poly(VSO3iPr6F40-co-HFISt28-co-t-BOCHFISt32) (Abs. 2.6) and an photoacid generator showed the contrast and sensitivity of 10.3 and 5.0 mJ cm-2, respectively.

Original languageEnglish
Pages (from-to)643-654
Number of pages12
JournalJournal of Photopolymer Science and Technology
Volume15
Issue number4
DOIs
Publication statusPublished - Jan 1 2002

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Bearings (structural)
Styrene
Sulfonic Acids
Photoresists
Free radical polymerization
Homopolymerization
Pyridine
Lithography
Density functional theory
Chlorides
Esters
Alcohols
Copolymers
Molecular weight
Polymerization
Acids
2,2-azobis(isobutyronitrile)
pyridine

All Science Journal Classification (ASJC) codes

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

Cite this

Fujigaya, T., Ando, S., Shibasaki, Y., Kishimura, S., Endo, M., Sasago, M., & Ueda, M. (2002). A new photoresist material for 157 nm lithography-2. Journal of Photopolymer Science and Technology, 15(4), 643-654. https://doi.org/10.2494/photopolymer.15.643

A new photoresist material for 157 nm lithography-2. / Fujigaya, T.; Ando, S.; Shibasaki, Y.; Kishimura, S.; Endo, M.; Sasago, M.; Ueda, M.

In: Journal of Photopolymer Science and Technology, Vol. 15, No. 4, 01.01.2002, p. 643-654.

Research output: Contribution to journalArticle

Fujigaya, T, Ando, S, Shibasaki, Y, Kishimura, S, Endo, M, Sasago, M & Ueda, M 2002, 'A new photoresist material for 157 nm lithography-2', Journal of Photopolymer Science and Technology, vol. 15, no. 4, pp. 643-654. https://doi.org/10.2494/photopolymer.15.643
Fujigaya, T. ; Ando, S. ; Shibasaki, Y. ; Kishimura, S. ; Endo, M. ; Sasago, M. ; Ueda, M. / A new photoresist material for 157 nm lithography-2. In: Journal of Photopolymer Science and Technology. 2002 ; Vol. 15, No. 4. pp. 643-654.
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AB - Time-dependent density functional theory (TD-DFT) calculations using the B3LYP hybrid functional suggested that sulfonic acid esters are transparent at around 157 nm region. Based on these findings, poly(methyl vinyl sulfonate) [poly(VSO3Me)] was prepared and found to have an extremely low absorbance (Abs.) of 2.2 μm-1 at 157 nm. Various alkyl vinyl sulfonates (VSO3R)s were prepared from 2-chloroethanesulfonyl chloride and alcohol components in the presence of pyridine, and their radical polymerizations were conducted in bulk using 2,2′-azobis(isobutyronitrile) as an initiator. Polymerizations of primary and secondary VSO3Rs bearing small alkyl substituents gave homopolymers with high molecular weights. Among them, the Abs. of poly(2,2,2-trifluoroethyl vinyl sulfonate) reached to 1.3 μm-1. Various copolymers from alkyl vinyl sulfonates and 4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropyl)styrene (HFISt) were also prepared and the Abs. of poly(1,1,1,3,3,3-hexafluoroisopropyl vinyl sulfonate40-co-HFISt60) [poly(VSO3iPr6F40-co-HFISt60)] was found to be 2.4 μm-1 at 157 nm. The photoresist consisting of partially t-BOC-protected poly(VSO3iPr6F40-co-HFISt28-co-t-BOCHFISt32) (Abs. 2.6) and an photoacid generator showed the contrast and sensitivity of 10.3 and 5.0 mJ cm-2, respectively.

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