A Steady Operation of n-Type Organic Thin-Film Transistors with Cyano-Substituted Distyrylbenzene Derivative

Abstract

A novel n-type organic semiconductor, cyano-substituted distyrylbenzene derivative, 1,4-bis{2-[4-(trifluoromethyl)phenyl]acrylonitorile}benzene, was synthesized by Knoevenagel condensation with aldehyde and acetonitrile derivatives. Fabricated thin-film transistors (TFTs) exhibited high electron field-effect mobility of 10 À2 -10 À1 cm 2 V À1 s À1 , on/off current ratio of 6 Â 10 5 . Hysteresis-free n-type transport characteristics observed in this device promises a steady operation of organic logic circuit. Almost same TFT characteristic was observed even after 1 month storage in ambient condition. The findings indicate that the material has a good resistance to atmospheric oxidants.

Molecular Structure and Crystal Packing of n-Type Semiconducting Material 3′,3′-(1,4-Phenylene)bis{2′-(4′′-trifluoromethyl)phenyl}acrylonitrile

“…In this reason electron carrier mobility between the molecules seems to be not good compared with the nearly perfect planar compound. Nevertheless, the n-type semiconducting property was very good that we previously reported [9,10]. Crystal packing of the compound was shown in Figure 2.…”

“…Since thin-film transistor (TFT) is the most fundamental electronic device in electronic circuit, improvement of OTFT performance is desired [1][2][3]. Although there are many reports of new candidate organic semiconductor having high mobility, only few reports mentioned drifting characteristics of on-current in OTFTs at onstate [4,5].…”

“…Recently, we reported excellent n-type transport characteristics of p-phenylenevinylene derivative of 3 ,3 -(1,4-phenylene)bis{2 -(4 -trifluoromethyl)phenyl}acrylonitorile having two cyano (CN) and two trifluoromethyl (CF 3 ) substituents [9]. We also reported the detailed synthetic methods of the compound and its analogues as Japan, Europe, and US patents [10].…”

Synthesis of Two Novels-Shaped Dibenzo[c,l] Chrysene Derivatives, Crystal Structure, and the Evaluation of their Photophysical Properties

“…We employed the typical Wittig and iodine-assisted photocyclization strategy for the synthesis of these molecules [17,18]. Earlier, we reported the synthesis of various kinds of polyaromatic compounds and evaluated their organic photoelectronic properties [19][20][21][22]. We believe that this study may be helpful to the material chemists in designing new materials with a view to achieve desired performance in devices and circuits.…”

“…The dihedral angle between the planes of the end phenyl rings was quite large (66.33°). Six phenyl ring planes, A (defined by C1,C2,C3,C4,C17,C18), B (defined by C5,C6,C17,C18,C19,C20), C (defined by C7,C8,C19,C20,C21,C22), D (defined by C15,C16,C21,C22,C23,C24), E (defined by C13,C14,C23,C24,C25,C26), and F (defined by C9,C10,C11,C12,C25,C26) were slightly leaned ( Figure 2), and the plane angles between the six phenyl rings are 14.10° for A-B, 25.59° for A-C, 11.54° for B-C, 19.90° for C-D, 31.34° for C-E, 42.52° for C-F, 28.89°, 27.83° for B-E, and 66.33° for A-E, respectively. The dihedral angles between the planes of the rings suggest that the shape of the molecule 4b seems to be planar, but it is a strained one.…”