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

Noria derivatives with pendant methoxy and adamantyl ester moieties (noriaMP-ADn) were synthesized by the substitution reaction of noria analogues with 12 methoxy groups (noriaMP) and 2-bromoacetyloxy-2-methyladamantane (BMA), and their degrees of introduction of adamantyl ester moieties (DI) could be controlled by the feed ratios of noriaMP and BMA. The physical properties such as solubility, film-forming ability, and thermal stability of noriaMP-ADn were also examined to assess the suitability for application as extreme ultraviolet (EUV)-resist materials. The patterning property of noriaMP-AD18 (DI = 18) and noriaMP-AD54 (DI = 54) was investigated in an EUV-resist system, and noriaMP-AD18 yielded higher resolution than noriaMP-AD54, 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/cm2.

► Noria derivatives with pendant methoxy and adamantate moieties were synthesized. ► The physical properties were differences in the values of adamantyl ester moieties. ► The sensitivity was efficient in extreme ultraviolet resist system. ► Resist pattern of 32 nm could be obtained in extreme ultraviolet resist system.