Synthesis and property of noria (water-wheel like macrocycle) derivatives with pendant alkoxyl and adamantyl ester groups, and their application for extreme ultraviolet resist

Abstract Noria derivatives with pendant methoxy and adamantyl ester moieties (noria MP -AD n ) were synthesized by the substitution reaction of noria analogues with 12 methoxy groups (noria MP ) and 2-bromoacetyloxy-2-methyladamantane (BMA), and their degrees of introduction of adamantyl ester moieties (DI) could be controlled by the feed ratios of noria MP and BMA. The physical properties such as solubility, film-forming ability, and thermal stability of noria MP -AD n were also examined to assess the suitability for application as extreme ultraviolet (EUV)-resist materials. The patterning property of noria MP -AD 18 (DI = 18) and noria MP -AD 54 (DI = 54) was investigated in an EUV-resist system, and noria MP -AD 18 yielded higher resolution than noria MP -AD 54 , providing a clear line and space pattern with a resolution of 32 nm and a line-width roughness of 10.5 nm by exposure dose of 9.0 mJ/cm 2 .