Birhodanines and their sulfur analogues for air-stable n-channel organic transistors

Abstract

International audienceA series of thin-film n-channel organic field-effect transistors based on various birhodanines, 3,3'-dialkyl-5,5'-bithiazolidinylidene-2,2'-dione-4,4'-dithiones (OS-R) and their sulfur analogues, 3,3'-dialkyl-5,5'-bithiazolidinylidene-2,4,2',4'-tetrathiones (SS-R) are studied. The SS-R compounds have tilted stacking crystal structures, whereas the OS-R compounds show basically herringbone structures. The alkyl chain R length and the intermolecular S-S interactions influence the molecular packing to realize excellent long-term air stability in the thin-film transistors

Temperature-dependent characteristics of n-channel transistors based on 5,5′-bithiazolidinylidene-2,4,2′,4′-tetrathiones

“…Elecrtochemical properties SS-R (R = Pr, Pen, and Hex) were prepared according to the method reported in Ref. 2…”

“…Crystal data of SS-Pen and SS-Hex are listed in Table 2 together with those of SS-Pr. 2 SS-Pen and SS-Hex are isostructural, but the structure is different from SS-Pr. SS-Pr makes a stacking structure (//a), in which the molecules are displaced along the molecular short axis ( Fig.…”

“…[1][2][3] These materials are obtained as a side-product of single-component organic metals, 4,5 but seemingly a very stable compound, 6 and show a strong acceptor ability, whose lowest unoccupied molecular orbitals (LUMO) are located around −4.2 eV. 2 We have first found the excellently air-stable n-channel transistor properties mainly in the single-crystal transistors of the ethyl compound (SS-Et), 1 but later found similar performance and air stability in the evaporated films of the n-propyl compound (SS-Pr). 2 The alkyl chain length has been increased up to n-butyl, but the performance decreases, 2 though the 2-phenylethyl compound shows a comparatively high mobility of 0.27 cm 2 V -1 s -1 .…”

“…2 We have first found the excellently air-stable n-channel transistor properties mainly in the single-crystal transistors of the ethyl compound (SS-Et), 1 but later found similar performance and air stability in the evaporated films of the n-propyl compound (SS-Pr). 2 The alkyl chain length has been increased up to n-butyl, but the performance decreases, 2 though the 2-phenylethyl compound shows a comparatively high mobility of 0.27 cm 2 V -1 s -1 . 3 Besides these tetrathione derivatives, the 2,2'-dione-4,4'dithione derivatives (OS-R), regarded as a dimer of rhodanine, 2,7 show similar transistor properties, though the performance and air stability are slightly reduced.…”

“…2 The alkyl chain length has been increased up to n-butyl, but the performance decreases, 2 though the 2-phenylethyl compound shows a comparatively high mobility of 0.27 cm 2 V -1 s -1 . 3 Besides these tetrathione derivatives, the 2,2'-dione-4,4'dithione derivatives (OS-R), regarded as a dimer of rhodanine, 2,7 show similar transistor properties, though the performance and air stability are slightly reduced. In the present work, we have focused on SS-R, and investigated the temperature dependence of the transistor properties.…”