Spectroscopic characterization of molecular interactions between DNQ-PACs and phenolic resins using selectively nitrogen-15 labeled DNQs

Marie Borzo; Joseph J. Rafalko; Monica Joe; Ralph R. Dammel; M. Dalil Rahman; Martine A. Ziliox

doi:10.1117/12.210350

9 June 1995 Spectroscopic characterization of molecular interactions between DNQ-PACs and phenolic resins using selectively nitrogen-15 labeled DNQs

Marie Borzo, Joseph J. Rafalko, Monica Joe, Ralph R. Dammel, M. Dalil Rahman, Martine A. Ziliox

Author Affiliations +

Proceedings Volume 2438, Advances in Resist Technology and Processing XII; (1995) https://doi.org/10.1117/12.210350
Event: SPIE's 1995 Symposium on Microlithography, 1995, Santa Clara, CA, United States

Abstract

Interactions between diazonaphthoquinone (DNQ)-photoactive compounds (PACs) and phenolic resins with different degrees of ortho, ortho-bonding have been investigated using solid state nitrogen-15 nuclear magnetic resonance (NMR) and vibrational (infrared and Raman) spectroscopic techniques. A specifically nitrogen-15 labeled PAC was synthesized to facilitate solid state nitrogen-15 NMR experimentation, and to resolve ambiguities in vibrational spectra. Comparison of vibrational spectra of the ¹⁵N-labeled PAC and its natural abundance ¹⁴N analog showed conclusively that Fermi resonance as well as hydrogen-boding resin-PAC interactions influence changes in the out-of-phase diazo stretching region near 2100 cm^-1. Solid state nitrogen-15 NMR of the ¹⁵N-labeled PAC in poly(p-hydroxystyrene), in a m-cresol 3,5-xylenol novolak, and in a mainly m,p- cresol novolak showed the binding situation in the resins to be diffuse, but quite similar. Although the three resins examined are lithographically very different, the observed nitrogen- 15 shifts were small compared to the broadening of the resonances, and did not show major differences due to ortho, ortho-bonding effects.

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Marie Borzo, Joseph J. Rafalko, Monica Joe, Ralph R. Dammel, M. Dalil Rahman, and Martine A. Ziliox "Spectroscopic characterization of molecular interactions between DNQ-PACs and phenolic resins using selectively nitrogen-15 labeled DNQs", Proc. SPIE 2438, Advances in Resist Technology and Processing XII, (9 June 1995); https://doi.org/10.1117/12.210350

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