New photoresist materials for 157-nm lithography. Poly[vinylsulfonyl fluoride-co-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropyl)-styrene] partially protected with tert-butoxycarbonyl

Tsuyohiko Fujigaya, Yuji Sibasaki, Shinji Ando, Shinji Kishimura, Masayoshi Endo, Masaru Sasago, Mitsuru Ueda

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Our molecular orbital calculations predicted excellent transparencies of molecules having sulfonyl fluoride groups in the vacuum ultraviolet (VUV) region. An optical density (OD) measurement of poly(vinylsulfonyl fluoride) [poly(VSF)] prepared by free radical polymerization of VSF clearly supported this calculation (OD = 2.1μm-1 at 157 nm). A new copolymer, poly [(VSF)40-co-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropyl)styrene (HFISt)60] [poly(VSF40-co-HFISt60)] prepared by free radical copolymerization of VSF and HFIST showed good transparency (OD = 2.4μm-1) as well. Poly(VSF40-co-HFISt22-co-tert-butoxycarbonyl HFISt38) (OD = 2.8μm-1) was prepared from poly(VSF40-co-HFISt60) and di-tert-butyl dicarbonate in the presence of 4-(dimethylamino)pyridine (DMAP). A resist film consisting of poly(VSF40-co-HFISt22-co-tert-Boc HFISt38) and 5 wt % triphenylsulfonium triflate showed a sensitivity of 7.2 mJ cm-2 and a contrast of 3.1 when a 150-nm-thick film prebaked at 100 °C for 1 min was exposed to 157-nm laser, postbaked at 130 °C for 1 min, and developed with a 2.38 wt % tetramethylammonium hydroxide (TMAH) aqueous solution.

Original languageEnglish
Pages (from-to)1512-1517
Number of pages6
JournalChemistry of Materials
Volume15
Issue number7
DOIs
Publication statusPublished - Apr 8 2003
Externally publishedYes

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Styrene
Density (optical)
Photoresists
Fluorides
Lithography
Transparency
Orbital calculations
Molecular orbitals
Free radical polymerization
Free radicals
Thick films
Pyridine
Copolymerization
Free Radicals
Copolymers
Vacuum
Molecules
Lasers

All Science Journal Classification (ASJC) codes

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

Cite this

New photoresist materials for 157-nm lithography. Poly[vinylsulfonyl fluoride-co-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropyl)-styrene] partially protected with tert-butoxycarbonyl. / Fujigaya, Tsuyohiko; Sibasaki, Yuji; Ando, Shinji; Kishimura, Shinji; Endo, Masayoshi; Sasago, Masaru; Ueda, Mitsuru.

In: Chemistry of Materials, Vol. 15, No. 7, 08.04.2003, p. 1512-1517.

Research output: Contribution to journalArticle

Fujigaya, Tsuyohiko ; Sibasaki, Yuji ; Ando, Shinji ; Kishimura, Shinji ; Endo, Masayoshi ; Sasago, Masaru ; Ueda, Mitsuru. / New photoresist materials for 157-nm lithography. Poly[vinylsulfonyl fluoride-co-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropyl)-styrene] partially protected with tert-butoxycarbonyl. In: Chemistry of Materials. 2003 ; Vol. 15, No. 7. pp. 1512-1517.
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abstract = "Our molecular orbital calculations predicted excellent transparencies of molecules having sulfonyl fluoride groups in the vacuum ultraviolet (VUV) region. An optical density (OD) measurement of poly(vinylsulfonyl fluoride) [poly(VSF)] prepared by free radical polymerization of VSF clearly supported this calculation (OD = 2.1μm-1 at 157 nm). A new copolymer, poly [(VSF)40-co-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropyl)styrene (HFISt)60] [poly(VSF40-co-HFISt60)] prepared by free radical copolymerization of VSF and HFIST showed good transparency (OD = 2.4μm-1) as well. Poly(VSF40-co-HFISt22-co-tert-butoxycarbonyl HFISt38) (OD = 2.8μm-1) was prepared from poly(VSF40-co-HFISt60) and di-tert-butyl dicarbonate in the presence of 4-(dimethylamino)pyridine (DMAP). A resist film consisting of poly(VSF40-co-HFISt22-co-tert-Boc HFISt38) and 5 wt {\%} triphenylsulfonium triflate showed a sensitivity of 7.2 mJ cm-2 and a contrast of 3.1 when a 150-nm-thick film prebaked at 100 °C for 1 min was exposed to 157-nm laser, postbaked at 130 °C for 1 min, and developed with a 2.38 wt {\%} tetramethylammonium hydroxide (TMAH) aqueous solution.",
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T1 - New photoresist materials for 157-nm lithography. Poly[vinylsulfonyl fluoride-co-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropyl)-styrene] partially protected with tert-butoxycarbonyl

AU - Fujigaya, Tsuyohiko

AU - Sibasaki, Yuji

AU - Ando, Shinji

AU - Kishimura, Shinji

AU - Endo, Masayoshi

AU - Sasago, Masaru

AU - Ueda, Mitsuru

PY - 2003/4/8

Y1 - 2003/4/8

N2 - Our molecular orbital calculations predicted excellent transparencies of molecules having sulfonyl fluoride groups in the vacuum ultraviolet (VUV) region. An optical density (OD) measurement of poly(vinylsulfonyl fluoride) [poly(VSF)] prepared by free radical polymerization of VSF clearly supported this calculation (OD = 2.1μm-1 at 157 nm). A new copolymer, poly [(VSF)40-co-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropyl)styrene (HFISt)60] [poly(VSF40-co-HFISt60)] prepared by free radical copolymerization of VSF and HFIST showed good transparency (OD = 2.4μm-1) as well. Poly(VSF40-co-HFISt22-co-tert-butoxycarbonyl HFISt38) (OD = 2.8μm-1) was prepared from poly(VSF40-co-HFISt60) and di-tert-butyl dicarbonate in the presence of 4-(dimethylamino)pyridine (DMAP). A resist film consisting of poly(VSF40-co-HFISt22-co-tert-Boc HFISt38) and 5 wt % triphenylsulfonium triflate showed a sensitivity of 7.2 mJ cm-2 and a contrast of 3.1 when a 150-nm-thick film prebaked at 100 °C for 1 min was exposed to 157-nm laser, postbaked at 130 °C for 1 min, and developed with a 2.38 wt % tetramethylammonium hydroxide (TMAH) aqueous solution.

AB - Our molecular orbital calculations predicted excellent transparencies of molecules having sulfonyl fluoride groups in the vacuum ultraviolet (VUV) region. An optical density (OD) measurement of poly(vinylsulfonyl fluoride) [poly(VSF)] prepared by free radical polymerization of VSF clearly supported this calculation (OD = 2.1μm-1 at 157 nm). A new copolymer, poly [(VSF)40-co-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropyl)styrene (HFISt)60] [poly(VSF40-co-HFISt60)] prepared by free radical copolymerization of VSF and HFIST showed good transparency (OD = 2.4μm-1) as well. Poly(VSF40-co-HFISt22-co-tert-butoxycarbonyl HFISt38) (OD = 2.8μm-1) was prepared from poly(VSF40-co-HFISt60) and di-tert-butyl dicarbonate in the presence of 4-(dimethylamino)pyridine (DMAP). A resist film consisting of poly(VSF40-co-HFISt22-co-tert-Boc HFISt38) and 5 wt % triphenylsulfonium triflate showed a sensitivity of 7.2 mJ cm-2 and a contrast of 3.1 when a 150-nm-thick film prebaked at 100 °C for 1 min was exposed to 157-nm laser, postbaked at 130 °C for 1 min, and developed with a 2.38 wt % tetramethylammonium hydroxide (TMAH) aqueous solution.

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