Z-shaped polycyclic aromatic hydrocarbons with embedded five-membered rings and their application in organic thin-film transistors†‡

Sven M. Elbert , Evelin Bolgert , Owen T. A. Paine , Farhad Ghalami , Wen-Shan Zhang , Ute Zschieschang , Frank Rominger , Dennis Popp , Hagen Klauk , Marcus Elstner , Michael Mastalerz
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Abstract

Z-shaped polycyclic hydrocarbons with embedded five-membered rings as well as their diaza-analogues have been synthesized. Soluble congeners were obtained by the introduction of mesityl substituents and studied by cyclo- as well as differential pulse voltammetry revealing an amphoteric redox behavior. Unsubstituted congeners showed close π-stacking in single crystal X-ray diffraction analyses and thus promising characteristics for the application as semiconducting materials in p-channel thin-film transistors (TFTs). The hole transport characteristics of the corresponding devices were investigated by GIWAXS.

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具有嵌入式五元环的 Z 形多环芳烃及其在有机薄膜晶体管中的应用
我们合成了内嵌五元环的 Z 型多环烃及其重氮类似物。通过引入间苯二酚取代基获得了可溶性同系物,并通过环伏安法和差分脉冲伏安法进行了研究,结果显示了两性氧化还原行为。未取代的同系物在单晶 X 射线衍射分析中显示出紧密的 π 堆积,因此具有在 p 沟道薄膜晶体管(TFT)中用作半导体材料的良好特性。通过 GIWAXS 研究了相应器件的空穴传输特性。
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