Issue 22, 2015

The structure–property relationship study of electron-deficient dihydroindeno[2,1-b]fluorene derivatives for n-type organic field effect transistors

Abstract

A bridged syn triphenylene derivative, namely 5,7-dihydroindeno[2,1-b]fluorene, functionalized with dicyanovinylene units (2,1-b)-IF([double bond, length as m-dash]C(CN)2)2 has been designed, synthesized and characterized. Its optical and electrochemical properties have been carefully studied through a combined experimental and theoretical approach and compared to those of three other structurally related dihydro[2,1-b]indenofluorene derivatives bearing methylenes, (2,1-b)-IF, carbonyls, (2,1-b)-IF([double bond, length as m-dash]O)2, or both carbonyl and dicyanovinylene, (2,1-b)-IF([double bond, length as m-dash]O)([double bond, length as m-dash]C(CN)2) on the bridgeheads. (2,1-b)-IF([double bond, length as m-dash]C(CN)2)2, which possesses a very low LUMO level, ca. −3.81 eV, has been successfully used as an active layer in n-channel OFETs using an epoxy based photoresist SU-8 as the gate insulator. (2,1-b)-IF([double bond, length as m-dash]C(CN)2)2 based n-channel OFETs show promising properties such as a low threshold voltage functioning of 7.2 V (low gate–source and drain–source voltages), a high ratio between the on and the off currents (6.3 × 105), interesting subthreshold swing (SS = 2.16) and electron mobility (>10−3 cm2 V−1 s−1) and excellent stability under electrical stress. This electrical stability has allowed the incorporation of (2,1-b)-IF([double bond, length as m-dash]C(CN)2)2 based n-channel OFETs in an integrated circuit. Thus, as a proof of concept, pseudo CMOS inverters made of n-type (2,1-b)-IF([double bond, length as m-dash]C(CN)2)2-based OFETs have been fabricated and characterized highlighting the potential of this new family of materials.

Graphical abstract: The structure–property relationship study of electron-deficient dihydroindeno[2,1-b]fluorene derivatives for n-type organic field effect transistors

Supplementary files

Article information

Article type
Paper
Submitted
06 Feb 2015
Accepted
17 Apr 2015
First published
20 Apr 2015

J. Mater. Chem. C, 2015,3, 5742-5753

Author version available

The structure–property relationship study of electron-deficient dihydroindeno[2,1-b]fluorene derivatives for n-type organic field effect transistors

M. Romain, M. Chevrier, S. Bebiche, T. Mohammed-Brahim, J. Rault-Berthelot, E. Jacques and C. Poriel, J. Mater. Chem. C, 2015, 3, 5742 DOI: 10.1039/C5TC00355E

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