Abstract
A novel concept of acid proliferation to improve the photosensitivity of chemically amplified photoresist materials is described by presenting the autocatalytic fragmentation of acetoacetates having a (sulfonyloxy)methyl residue to liberate the corresponding sulfonic acid. 2-Methyl-2-((methane- or p-toluenesulfonyloxy)methyl)acetoacetates were designed to be subjected to the acid-catalyzed fragmentation through the corresponding acetoacetic acids which are readily decarboxylated and undergo the subsequent β-elimination to give a sulfonic acid which can act as the autocatalyst to lead to the increment of acid concentration in geometric progression. Among the acetoacetates tested, tert-butyl 2-methyl-2-((p-toluenesulfonyloxy)methyl)acetoacetate was the most suitable reagent for the present purpose because of its reasonable thermal stability. A nonlinear generation of the sulfonic acid was confirmed in the acidolytic transformation of the acetoacetate in nonpolar solvents and in a film of poly[4-((tert-butox...
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