Journal of the Korean Applied Science and Technology (한국응용과학기술학회지)

The Korean Society of Applied Science and Technology (한국응용과학기술학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis of novolac resins by condensation of phenolic compounds with formaldehyde

폐놀계 화합물과 포름알데히드의 축합반응으로부터 노볼락 레진의 합성

  • Lee, Jong-Dae (Department of Chemical Engineering, Chungbuk National University) ;
  • Lee, Tae-Jun (Department of Chemical Engineering, Chungbuk National University) ;
  • Lee, Chang-Hoon (Department of Chemical Engineering, Hanyang University) ;
  • Cho, Kyung-Tae (Department of Chemical Engineering, Chungbuk National University)
  • 이종대 (충북대학교 공과대학 화학공학과) ;
  • 이태준 (충북대학교 공과대학 화학공학과) ;
  • 이창훈 (한양대학교 화학공학과) ;
  • 조경태 (충북대학교 공과대학 화학공학과)
  • Published : 2007.09.30
Download PDF
⟨ Previous Next ⟩

Abstract

Novolac is widely used as the primary solid component of most photoresists in semiconductor and microelectronic devices. In this study, novolac resins were prepared by condensation of 35% formaldehyde with phenolic compounds such as m-/p-cresol, 2,5-dimethylphenol and bisphenol A in the presence of oxalic acid as catalyst. The average molecular weight $(M_w)$ of these novolac resins has been varied on the changing of mixing ratio of m-/p-cresol/2,5-dimethylphenol/bisphenol A or formaldehyde/phenolic compound. Also, thermal properties of novolac were observed by TGA.

Keywords

References

  1. A. Knop and L.A. Pilato, 'Phenolic Resin', p. 1, Spinger-Verlag, Berlin (1986)
  2. A. Furuta, M. Hanabata and Y. Uemura, High Performance Positive Photoresists, J. Vac. Sci. Technol. B, 4, 430 (1986) https://doi.org/10.1116/1.583349
  3. S. Miloshev, P. Novakov, V. Dimitrov and I. Gitsov, Synthesis of Novolac Resins: 2. Influence of The Reaction Medium on The Properties of the Novolac Oligomers, Polymer, 32, 3067 (1991) https://doi.org/10.1016/0032-3861(91)90211-Z
  4. L. E. Bogan, Determination of Cresol Novolak Copolymer Composition and Branch Density Using Carbon-13 NMR Spectroscopy, Macromolecules, 24, 4807 (1991) https://doi.org/10.1021/ma00017a012
  5. E. Bogan, The Novolak Synthesis Reaction: A Description Based on Reactivities, Macromolecules, 25, 1966 (1992) https://doi.org/10.1021/ma00033a021
  6. T. F. Yeh, H. Y. Shih and A. Reiser, Percolation View of Novolak Dissolution and Dissolution Inhibition, Macromolecules, 25, 5345 (1992) https://doi.org/10.1021/ma00046a037
  7. R. Yang, S. A. Soper and W. Wang, A New UV Lithography Photoresist Based on Composite of EPON Resins 165 and 154 for Fabrication of High-Aspect-Ratio Microstructures, Sens. Actuators A: Phys. 135, 625 (2007) https://doi.org/10.1016/j.sna.2006.09.009
  8. C. M. Berger and C. L. Henderson, The Effect of Humidity on Water Sorption in Photoresist Polymer Thin Films, Polymer, 44, 2101 (2003) https://doi.org/10.1016/S0032-3861(03)00079-X
  9. D. Roy, A. Gandhi, P. K. Basu, P. Raghunathan and S. V. Eswaran, Optimization of Monomer Content and Degree of Linearity in Lithographically Interesting Novolac Copolymers using NMR Spectroscopy, Microelectronic Ens., 70, 58 (2003) https://doi.org/10.1016/S0167-9317(03)00391-5
  10. P. J. de Bruyn, L. M. Foo, A. S. C. Lim, M. G. Looney and D. H. Solomon, The Chemistry of Novolac Resins. Part 4. The Strategic Synthesis of Model Compounds, Tetrahedron, 53, 13915 (1997) https://doi.org/10.1016/S0040-4020(97)00903-4
  11. M. Kobayashi, F. Sanda and T. Endo, Application of Phosphonium Ylides to Latent Catalysts for Polyaddition of Bisphenol A Diglycidyl Ether with Bisphenol A: Model System of Epoxy-Novolac Resin, Macromolecules, 32, 4751 (1999) https://doi.org/10.1021/ma990149z
  12. Z. Anthony, U. S. Patent 5,130,410 (1992)
  13. S. K. Lee and H. Lee, Synthesis and Properties of Mixed meta-and para-Cresol/Formaldehyde Novolak Resins, Polymer (Korea), 16, 662 (1992)
  14. U. Westerwelle, G. Bahr, G. Grutzner and F. Reuther, Partially Carboxymethylated Novolaks for Photoresist Systems: New Photoresists for Development under Mildly Alkaline Conditions, Microelectronic Eng., 41/42, 343 (1998) https://doi.org/10.1016/S0167-9317(98)00079-3
  15. U. Yasunori, M. Hiroshi, and T. Yoshiyuki, U. S. Patent 6,815,140 (2004)