p-Toluenesulfonate Ester Derivatives of Benzendiol as Novel Acid Amplifiers

새로운 산증식제로 벤젠다이올의 p-톨루엔술폰산 에스터 유도체에 관한 연구

  • 강지은 (부경대학교 공과대학 화상정보공학부) ;
  • 홍경일 (한국화학연구원 복합기능환경소재팀) ;
  • 임권택 (부경대학교 공과대학 화상정보공학부) ;
  • 정연태 (부경대학교 공과대학 화상정보공학부)
  • Received : 2005.04.12
  • Accepted : 2005.08.01
  • Published : 2005.10.10

Abstract

Aiming the development of novel acid amplifiers, 2-hydroxyphenyl-4-methylbenzenesulfonate (1), 3-hydroxyphenyl-4-methylbenzene sulfonate (2), 4-hydroxyphenyl-4-methylbenzenesulfonate (3) were synthesized as the aromatic acid amplifiers with good thermal stability. They were autocatalytically generated p-toluenesulfonic acid in the presence of small amount of acid evolved from a photoacid generator. These aromatic sulfonates showed excellent thermal stability in PtBMA film and were proven to be the first aromatic acid amplifier to act as a photosensitivity enhancer. When these compounds were coupled with a chemically amplified photoresist system, photosensitivity was enhanced up to 3~6 folds.

References

  1. S. Kaur, J. V. Crivello, and N. Pascuzzi, J. Polym. Sci., 37, 199 (1999) https://doi.org/10.1002/pol.1959.1203713115
  2. S. J. Bukofsky, G. D. Feke, Q. Wu, R. D. Grober, P. M. Dentinger, and J. W. Taylor, Appl. Phys. Lett., 73, 408 (1998) https://doi.org/10.1063/1.121850
  3. S. W. Park, K. Arimitsu, S. G. Lee, and K. lchimura, Chem. Lett., 1036 (2000)
  4. H. Ito, Proc. SPIE., 3678, 2 (1999)
  5. H. Ito, K. Arimitsu, and K. lchimura, Macromol, Chem. Phys., 201, 132 (2000)
  6. W. S. Huang, R. E. Kwong, and W. Moreau, Proc. SPIE, 591, 3999 (2000)
  7. A. R. Pawloski, Christian, and P. F. Nealey, J. Am. Chem. Soc., 13, 4154 (2001)
  8. E. J. Lee, J. Y. Park, and Y. T. Jeong, J. Kor. Soc. Imaging Sci. Technol., 7, 110 (2001)
  9. E. J. Lee, K. A. Kuen, and Y. T. Jeong, J. Kor. Printing. Soc., 20, 91 (2002)
  10. E. J. Lee, K. I. Hong, K. T. Lim, Y. S . Jeoung, S. S. Hong, and Y. T. Jeong, J. Kor. Chem. Soc., 46, 437 (2002) https://doi.org/10.5012/jkcs.2002.46.5.437
  11. K. I. Hong, E. J. Lee, K. T. Lim, Y. S. Jeong, and Y. T. Jeong, J. Kor. Ind. Eng. Chem., 14, 605 (2003)
  12. K. I. Hong, Y. S. Jeong, K. T. Lim, S. J. Choi, and Y. T. Jeong, J. Ind. Eng. Chem., 10, 864 (2004)