Facile Synthesis of Bis‐pentafluoroarylated Anthracene Derivatives for N‐type Organic‐Field‐Effect Transistor Applications
Ryota Sato, Takeshi Yasuda, Takanobu Hiroto, Takaki Kanbara, Junpei Kuwabara
Abstract
Abstract Diphenylanthracene (DPA) and its derivatives are promising semiconducting materials for p‐type organic‐field‐effect transistors (OFETs). In this study, to develop n‐type semiconducting materials with an anthracene core, pentafluorobenzene was introduced into anthracene by C−H direct arylation, enabling the synthesis of various bis(pentafluorophenyl)anthracene (DPA−F) derivatives. The high reactivity of the pentafluorobenzene C−H bond allows direct arylation for synthesizing DPA−F derivatives in a single step. The introduction of strong electron‐withdrawing pentafluorophenyl groups provides the anthracene derivatives with n‐type semiconducting properties, in contrast to the p‐type properties of the parent DPAs. Among the synthesized compounds, 2,6‐bis(pentafluorophenyl)anthracene shows a high electron mobility of 0.12±0.02 cm 2 /Vs and an on/off ratio>10 6 in OFETs. The high crystallinity results in the smooth electron transport. This study provides a facile synthetic method for n‐type semiconducting materials and insights into the molecular design of the positional effects of aromatic substituents on anthracene.