Novel water-developable negative resists were designed to induce both cross-linking and polarity change upon exposure and bake. The matrix polymers were synthesized by copolymerization of glyceryl methacrylate and methacrolein. The acid-catalyzed acetalization of the polymer induced cross-linking, polarity change, and increase in dry-etch resistance. The resist formulated with this polymer and cast in a water-ethanol mixture, showed 0.7 μm line and space patterns using a mercury-xenone lamp in a contact printing mode and pure water as a developer.
We have examined a novel class of ketal based deep UV photoresist. 1,4-Dioxaspiro(4,4)nonane-2-methyl methacrylate was synthesized and polymerized. A ketal group of poly(1,4- dioxaspiro(4,4)nonane-2-methyl methacrylate) hydrolyzes under acid catalysis to give two alcohol functionalities and a cyclopentanone molecule. The ketal polymer is insoluble in an aqueous developer, while the hydrolyzed products are soluble.It was found the cyclopentanone product affects diffusion of acid in the resist. As a result, the generated cyclopentanone increases mobility of the acid significantly.
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