The objective of research presented in this thesis is to design a novel 193 nm photoresist system based on the photo-Fries rearrangement of a formyloxyphenyl functional group. In pursuit of this goal, the synthesis of acrylic and norbornenyl-based polymer systems was carried out. In addition, studies of contrast curves, sensitivity, and developed images were conducted. In this research, 4-hydroxystyrene, formyloxystyrene, poly(formyloxystyrene-co-methylmethacrylate/methacrylic acid), poly(norbornene-co-hexafluoromethylisopropyl alcohol), norbornenylphenylacetate and norbornenylphenylformate were synthesized. The formyloxystyrene (FOxS) functional group absorbs strongly at 193 nm. However, by limiting the amount of FOxS in an acrylic or norbornenyl copolymer, resist systems with sufficient transparency at 193 nm can possibly be realized. Methylmethacrylate (MMA) and methacrylic acid (MAA) are well known as transparent resist components in base-developable, 193 nm, acrylic systems. In acrylic systems, MAA can bring the resist to the threshold for base solubility; and MMA or other acrylic monomers such as admantylmethacrylate serve as the transparent polar component of the resist. The latter monomer, adamantylmethacrylate, can increase the etch resistance of the resist system. Imaging results show that the acrylic system with formyloxystyrene functional groups has the potential to be the basis for a non-chemically amplified 193 nm photoresist. Today, chemically amplified resist systems derived from norbornenyl hexafluoromethylisopropyl alcohol are the benchmark materials for etch-resistance and transparency at 193 nm. In the present research, attempts were made to design and synthesize etch-resistant norbornene/norbornenylhexafluoromethylisopropyl alcohol/norbornenylphenylformate copolymers in which norbornenylphenylformate is the photo-sensitive resist component, and norbornenyl hexafluoromethylisopropyl alcohol is used to set the threshold for base solubility.
Library of Congress Subject Headings
Photoresists--Materials; Copolymers; Polymerization
Department, Program, or Center
School of Chemistry and Materials Science (COS)
Yin, Ran, "Synthesis of non-chemically amplified 193nm photo-resists based on copolymers containing formyloxybenzene functional groups" (2010). Thesis. Rochester Institute of Technology. Accessed from
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