Novel class of highly selective divanillin-based PACs

Arturo N. Medina; Lawrence Ferreira; Sobhy P. Tadros; Joseph J. Sizensky; M. Fregeolle; Andrew J. Blakeney; Medhat A. Toukhy

doi:10.1117/12.241843

14 June 1996 Novel class of highly selective divanillin-based PACs

Arturo N. Medina, Lawrence Ferreira, Sobhy P. Tadros, Joseph J. Sizensky, M. Fregeolle, Andrew J. Blakeney, Medhat A. Toukhy

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Proceedings Volume 2724, Advances in Resist Technology and Processing XIII; (1996) https://doi.org/10.1117/12.241843
Event: SPIE's 1996 International Symposium on Microlithography, 1996, Santa Clara, CA, United States

Abstract

A new class of diazonaphthoquinone (DNQ) photoactive compounds (PACs) based on the divanillin core is introduced in this paper. The general structure of these PAC backbones is shown in Formula 1. The divanillin structure possesses unique electronic characteristics which influence its DNQ-SO₂Cl esterification reactions to be highly selective. The most reactive site for esterification in Formula 1 is one of the divanillin hydroxyls despite the typically higher steric hindrance. Surprisingly, the esterification product is then significantly deactivated towards esterification at the other previously equivalent divanillin OH. The result of using 3 equivalents of DNQ-SO₂Cl to esterify tetraphenolic species is the formation of high percentages of the specific triester in which the second divanillyl OH remains unesterified. The deactivation of the second divanillin OH after the initial esterification indicates some interaction between the two o,o-biphenol rings despite its inability to be coplanar for conjugation of (pi) electrons because of steric hindrance. Possible explanations for this interaction are explored using molecular simulation tools. Diverse members of the divanillin PAC family have been prepared from phenols of varying structure and hydrophobicities. These PACs were tested lithographically and the results correlated with PAC backbone structure. The characteristic dissolution rate behavior of the resist formulations based on triesterified PACs, measured as a function of exposure dose, generally show high discrimination and strong inhibition, even with the more hydrophilic PACs. These formulations typically exhibited high resolution, wide focus latitude, and exposure margins greater than 2.0 in lithographic screening.

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Arturo N. Medina, Lawrence Ferreira, Sobhy P. Tadros, Joseph J. Sizensky, M. Fregeolle, Andrew J. Blakeney, and Medhat A. Toukhy "Novel class of highly selective divanillin-based PACs", Proc. SPIE 2724, Advances in Resist Technology and Processing XIII, (14 June 1996); https://doi.org/10.1117/12.241843

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KEYWORDS

Picture Archiving and Communication System

Lithography

Hydrogen

Electrons

Antimony

Carbon

Chlorine

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