Extreme Ultraviolet (EUV)-Resist Materials of Noria (Water Wheel-Like Cyclic Oligomer) Derivatives containing Acetal Moieties

Abstract

The synthesis and properties of noria derivatives (noria-CHVE's) with pendant acetal moieties were examined for application as extreme ultraviolet (EUV)-resist materials. The reaction of noria and cyclohexyl vinyl ether was carried out in the presence of pyridinium p-toluenesulfonate as a catalyst, to give the corresponding noria-CHVE's with various degrees of introduction (DI) of cyclohexyl acetal moieties by adjusting the feed ratio of reactant and reaction time. The physical properties (solubility, thermal stability, and film-forming ability) of noria-CHVE's were consistent with the differences in DI values. The patterning properties of noria-CHVE50 (DI = 50) and noria-CHVE59 (DI = 59) were investigated in an EUV-resist system, and it was found that noria-CHVE50 gave higher resolution than noria-CHVE59, providing a clear line and space pattern with a resolution of 37.9 nm and a line-edge roughness (LER) of 7.2 nm.