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Electrophilic Aromatic Functionalization of Phenolic Photoresist Polymers

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Summary

Functionalization of both linear poly(4-hydroxystyrene) (PHS) and branched poly(4-hydroxystyrene) (PHS-B) was accomplished via a Reimer-Tiemann electrophilic aromatic substitution reaction. Linear and branched poly(4-hydroxystyrene-co-5-vinylsalicylaldehyde) (pHS/5VSA and pHS-B/5VSA) copolymers were observed to undergo acid-catalyzed, novolac type self-crosslinking. Both the pHS/5VSA and pHS-B/5VSA copolymer systems possessed a lower deep ultra violet microlithographic sensitivity compared to linear PHS when formulated in negative photoresists. The sluggishness of the negative photoresists containing 5-vinylsalicylaldehyde functionalized copolymers was attributed to a combination of resonance stabilization and steric hindrance effects.

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References

  1. Moreau WM (1987) Semiconductor Lithography: Principles, Practices and Materials. Plenum Press, New York.

  2. Lee SM, Frechet JMJ, Willson CG (1994) Macromolecules 27:5154

    Google Scholar 

  3. Lee SM, Frechet JMJ (1994) Macromolecules 27:5160

    Google Scholar 

  4. Moskala EJ, Varnell DF, Coleman MM (1985) Polymer 26:228

    Google Scholar 

  5. Dai K, Kramer EJ, Frechet JMJ, Wilson PG, Moore RS, Long TE (1994) Macromolecules 27(18):5187 (1994)

    Google Scholar 

  6. Xu Z, Jandt KD, Kramer EJ, Edgecomb BD, Frechet JMJ (1995) J Polym Sci, Polym Phys 33:2351

    Google Scholar 

  7. Sounik J (1996) US Patent 5,554,719

  8. Sounik J (1996) US Patent 5,565,544

  9. Sounik J, Vicari R, Lu PH, Kokinda E, Ficner S, Dammel RR (1996) SPIE Advances in Resist Technology and Processing XIII 2724:196

  10. Smith MB and March J (2004) Advanced Organic Chemistry: Reactions, Mechanisms and Structure 5th Edition. Wiley-Interscience, New York

  11. Wynberg H, Meijer EW (1982) Organic Reactions 28:1

  12. Reiser A, (1989) Photoreactive Polymers: The Science and Technology of Resists. Wiley, New York

  13. Allinger NL (1977) J Am Chem Soc 99:8127

    Google Scholar 

  14. Pruthikul R, Coleman MM, Painter PC, Tan NB (2001) J Polym Sci, Polym Phys 39:1651

    Google Scholar 

  15. Beck B, Allen RD, Tweig RJ, Willson CG, Matuszczak S, Stover NHL, Frechet JMJ (1989) Polym Eng Sci 29(14):960

    Google Scholar 

  16. Frechet JMJ, Matuszczak S, Lee SM, Fahey J, Willson CG, Frechet JMJ (1992) Polym Eng Sci 32(20):1471

    Google Scholar 

  17. Stover HDH, Matuszczak, S, Willson CG, Frechet JMJ (1991) Macromolecules, 24(8):1741

    Google Scholar 

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Authors and Affiliations

  1. Department of Science and Mathematics, Kettering University, 1700 West Third Avenue, Flint, Michigan, 48504, USA

    Carl Lawrence Aronson, Douglas Beloskur, Isaac S. Frampton, Justin McKie & Paul Montbriand

Authors
  1. Carl Lawrence Aronson
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  2. Douglas Beloskur
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  3. Isaac S. Frampton
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  4. Justin McKie
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  5. Paul Montbriand
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Correspondence to Carl Lawrence Aronson.

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Aronson, C., Beloskur, D., Frampton, I. et al. Electrophilic Aromatic Functionalization of Phenolic Photoresist Polymers. Polym. Bull. 52, 409–419 (2004). https://doi.org/10.1007/s00289-004-0305-x

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  • DOI: https://doi.org/10.1007/s00289-004-0305-x

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