3-Phenyl-3,3-ethylenedioxy-1-propyl Sulfonates as Acid Amplifiers To Enhance the Photosensitivity of Positive-Working Photoresists

Abstract

In the presence of a small amount of acid, 3-phenyl-3,3-ethylenedioxy-1-propyl ptoluenesulfonate autocatalytically decomposed to give p-toluenesulfonic acid both in solution and in a polymer matrix. Such a reaction was successfully applied for the improvement of sensitivity of several positive-working chemical-amplification photoresists. It was revealed that the diffusion of the acid plays the most essential role in the sensitivity enhancement, by determining the addition effect of the acid amplifiers with various arenesulfonates on photosensitivity characteristics.

Sensitivity Enhancement of a Photocuring Material by Base Amplifiers.

“…The non-linear behavior of the base amplifiers is similar to that of acid amplifiers [8][9][10] which had been proposed in our laboratory. The addition of 1,3-bis[ l -(9-fluorenylmethoxycarbonyl)-4-piperidyl]propane (1) as a base amplifier liberating the corresponding secondary amine to an epoxy polymer sensitized with a photobase generator resulted in the enhancement of photoinduced insolubilization of the epoxy polymer to some extent.…”

Fluorinated Acid Amplifiers for EUV Lithography

“…Only two of the AAs produce fluorinated acids; 7 the others are either too difficult or expensive to synthesize, 8 do not decompose autocatalytically, 9 or are unstable under photoresist conditions. 10 Here, we report on the design and kinetics of four AAs and one thermal AA (Figure 1). 11 We compare the relative rates of autocatalyzed and uncatalyzed reactions and show the unprecedented ability of 3b to simultaneously improve resolution, sensitivity, and LER of EUV photoresists.…”

Fluorine-Stabilized Acid Amplifiers for Use in EUV Lithography

“…The undesirable decomposition pathway is uncatalyzed thermal decomposition which results in the formation of an olefin byproduct and an acid. Several acid amplifiers (20-30) were reported in the literature [6][7][8][9][10][11][12][13] prior to the beginning or our research in 2005.…”