Electron deficient dicyanovinylene-ladder-type pentaphenylene derivative for n-type Organic Field Effect Transistors

Emmanuel Jacques (1) , Maxime Romain (2) , Ali Yassin (2) , Sarah Bebiche (1) , Maxime Harnois (1) , Tayeb Mohammed-Brahim (1) , Joëlle Rault-Berthelot (2) , Cyril Poriel (2)

1 IETR - Institut d'Électronique et des Technologies du numéRique
2 ISCR - Institut des Sciences Chimiques de Rennes

A bridged pentaphenylene derivative functionalized with dicyanovinylene units LPP([double bond, length as m-dash]C(CN)2)2 has been designed, synthesized and characterized. The optical and electrochemical properties have been carefully studied through a combined experimental and theoretical approach and compared with those of two pentaphenylene derivatives bearing methylenes (LPP) or carbonyl (LPP([double bond, length as m-dash]O)2) on the bridgeheads. LPP([double bond, length as m-dash]C(CN)2)2 which possesses a very low LUMO level, ca. −4.02 eV, has been successfully used as an active layer in n-channel OFETs using the epoxy based photoresist SU-8 as a gate insulator. LPP([double bond, length as m-dash]C(CN)2)2 based n-channel OFETs show low voltage functioning (low gate-source and drain-source voltages), high ratio between the on and the off currents (2 × 105), interesting subthreshold swing (S = 1) and excellent stability under electrical stress and in a nitrogen atmosphere. More importantly, we have also shown that LPP([double bond, length as m-dash]C(CN)2)2 based n-channel OFETs present an excellent environmental stability. This work is to the best of our knowledge the first report on bridged pentaphenylene-based semiconductors in n-type OFETs and highlights the potential of such type of material to provide air stable OFETs.

Domaines: Matériaux

Emmanuel Jacques, Maxime Romain, Ali Yassin, Sarah Bebiche, Maxime Harnois, et al.. Electron deficient dicyanovinylene-ladder-type pentaphenylene derivative for n-type Organic Field Effect Transistors. Journal of Materials Chemistry C, 2014, 2 (17), pp.3292-3302. ⟨10.1039/C3TC31925C⟩. ⟨hal-01066947⟩