Journal of the Korean Institute of Electrical and Electronic Material Engineers (한국전기전자재료학회논문지)

The Korean Institute of Electrical and Electronic Material Engineers (한국전기전자재료학회)
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Effect of Aromatic Acid Amplifier, 2-hydroxy-2'-tosyloxy Biphenyl, on the kind of Resist Resins

방향족 산증식제 2-hydroxy-2'-tosyloxy Biphenyl의 레지스트 레진의 종류에 따른 효과에 관한 연구

  • 강지은 (부경대학교 화상정보공학) ;
  • 정용석 (부경대학교 화상정보공학) ;
  • 정연태 (부경대학교 화상정보공학)
  • Published : 2005.06.01

Abstract

We compared the effects of a representative aromatic acid amplifier, 2-hydroxy-2'-tosylory biphenyl, doped in poly(tort-butyl methacrylate) (PTBMA), poly (tetrahydropyranylmethacrylate) (pTHPMh) or poly[tert-butoxycarbonyloxystyrene) (pTBOCST) resin film as acid labile polymer in view of thermal stability and photosensitivity enhancement. The acid amplifier was stable up to 60 min in pTBMA and pTBOCST film and up to 10 min in pTHPMA film at $120^{\circ}C$. pTBMA and pTHPMA film doped with the acid amplifier showed 9 times and 3 times higher photosensitivity, respectively. But pTBOCST film showed a negligible photosensitivity enhancement. Photosensitivity enhancement and thermal stability of the acid amplifier were found to be affected by the resin.

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References

  1. S. W. Park, K. Arimitsu, S. G. Lee, and K. Ichimura, 'A novel photoresist based on polymeric acid amplifiers', Chem. Lett., Vol. 29, No.9, p. 1036, 2000
  2. W. S. Hwang, R. E. Kwong, and W. Moreau, 'Acid amplifiers-proton transfer or direct acid formation', Proc. SPIE, Vol. 3999, No.1, p. 591, 2000
  3. K. Ichimura, K. Arimitsu, and K. Kudo, 'A novel concept of acid proliferation. autocatalytic fragmentation of an acetoacetate derivative as an acid amplifier', Chem. Lett., Vol. 24, No.6, p. 551, 1995
  4. E. J. Lee, K. A. Kuen, and Y. T. Jeong, '1-Hydroxy-4-tosyloxy cyclohexane and 4-ditosyloxy cyclohexane as acid amplifiers to enhance the photosensitivity of positiveworking photoresists', J. Kor. Printing. Soc., Vol. 20, No.1, p. 91, 2002
  5. E. J. Lee, K. I. Hong, K. T. Lim, Y. S. Jeoung, S. S. Hong, and Y. T. Jeong, 'Preparation and characterzation of pstyrenesulfonates of isoproplidene dicyclohexnol as acid amplifiers to enhance the photosensitivity of positive-working photoresists', J. Kor. Chem. Soc., Vol. 46, No.5, p. 437, 2002.
  6. E. J. Lee, and J. Y. Park, and Y. T. Jeong, 'Synthesis and characterization of a novel acid amplifier(1)', J. Kor. Soc. Imaging Sci. Technol., Vol. 7, No.2, p. 110, 2001
  7. K. I. Hong, Y. S. Jeong, K. T. Lim, S. J. Choi, and Y. T. Jeong, 'p- ToJuenesulfonate esters of 1,2-benzenediol as novel acid amplifers', J. Ind. Eng. Chem., Vol. 10, No.5, p. 864, 2004
  8. G. N Taylor, L. E. Stillwagon, and F. M. Houlihan, 'Positive, chemically-amplified aromatic methacrylate resist employing the tetrahydropyranyl protecting group', Chem. Mater., Vol. 3, No.6, p. 1031, 1991
  9. J. M. J. Frechet, Eva Eichler, H. Ito, and C. G. willson, 'Polytp-tert-butoxycarbonyloxy styrene): a convenient precursor to p-hydroxystyrene resins', Polymer, Vol. 24, No.8, p. 995, 1983
  10. W. Conley, C. Babcock, N. Farrar,H. Y. Liu, B. Peterson, and K. Taira, 'Comparisons of critical parameters for high and low activation energy deep UV photoresists', Proc. SPIE, Vol. 3333, No.1, p. 357, 1998
  11. E. J. Lee, K. I. Hong, Y. S. Jeoung, K. T. Lim, and Y. T. Jeong, 'Effect of phenolic derivatives on thermal decomposition of sulfonate esters', J. Kor. Soc. Imaging Sci. Technol., Vol. 9, No.1, p. 27, 2003
  12. G. G. Barclay, D. R. Medeiros, and R. F. Sinta, 'Thermal stability of sulfonate ester photoacid generators in phenolic matrices', Chem. Mater., Vol. 7, No.7, p. 1315, 1995 https://doi.org/10.1021/cm00059a002
  13. E. Reichmanis, F. M. Houlihan, O. Nalamasu, and T. X. Neenan, 'Chemical amplification mechanisms for microlithography', Chem. Mater., Vol. 3, No.3, p. 394, 1991