High‐Mobility Regioisomeric Thieno[f,f′]bis[1]benzothiophenes: Remarkable Effect of Syn/Anti Thiophene Configuration on Optoelectronic Properties, Self‐Organization, and Charge‐Transport Functions in Organic Transistors,Advanced Electronic Materials

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High‐Mobility Regioisomeric Thieno[f,f′]bis[1]benzothiophenes: Remarkable Effect of Syn/Anti Thiophene Configuration on Optoelectronic Properties, Self‐Organization, and Charge‐Transport Functions in Organic Transistors
Advanced Electronic Materials ( IF 5.3 ) Pub Date : 2017-12-04 , DOI: 10.1002/aelm.201700390
Tatsuya Oyama _{1,

2} , Tatsuya Mori _{1,

2} , Tomohiro Hashimoto ₃ , Muneaki Kamiya _{3,

4} , Takahiro Ichikawa ₅ , Hideaki Komiyama ₁ , Yu Seok Yang ₁ , Takuma Yasuda _{1,

2}

Affiliation

π‐Conjugated thienoacene‐based organic semiconductors with high charge carrier mobility and processability have been intensively pursued for electronic device applications, including organic field‐effect transistors (OFETs). Their charge carrier mobility is an important figure of merit, and is influenced not only by the intrinsic electronic structure at molecular level, but also by the molecular packing arrangement and crystallinity in the solid state. In this work, the focus is on a unique regioisomeric thienoacene system involving dialkyl‐thieno[f,f′]bis[1]benzothiophene isomers having different syn/anti thiophene configurations (syn‐ and anti‐TBBT‐8). The effects of these regioisomeric structures on the physicochemical properties, self‐organization behavior, and charge‐transport functions are systematically investigated using experimental and theoretical analyses. The structural analyses indicate that the syn‐ and anti‐TBBT‐8 isomers self‐organize into completely different packing arrangements, in the form of solution‐crystallized microribbons and thin films. The resulting charge‐transport properties are strongly dependent on the syn/anti thiophene configurations. Remarkably, solution‐processed OFETs using the syn‐TBBT‐8 isomer show high hole mobilities of up to 10.1 cm² V⁻¹ s⁻¹, which are more than one order of magnitude higher than those of the anti‐TBBT‐8 isomer. This work highlights the importance of the regioisomeric molecular configuration of thienoacene‐based organic semiconductors for developing high‐performance electronic devices.

中文翻译：

高迁移性区域异构噻吩并[f，f'] bis [1]苯并噻吩：顺/反噻吩构型对有机晶体管中光电性能，自组织和电荷传输功能的显着影响

具有高电荷载流子迁移率和可加工性的π共轭噻吩并噻吩基有机半导体已被广泛用于电子设备应用，包括有机场效应晶体管（OFET）。它们的电荷载流子迁移率是重要的品质因数，不仅受分子水平上固有的电子结构的影响，而且还受分子堆积结构和固态结晶度的影响。在这项工作中，重点是独特的区域异构硫杂并苯体系，该体系涉及具有不同顺/反噻吩构型（顺-和反-噻吩构型的二烷基-噻吩并[ f，f '] bis [1]苯并噻吩异构体-TBBT-8）。使用实验和理论分析系统地研究了这些区域异构结构对理化性质，自组织行为和电荷传输功能的影响。结构分析表明，顺式和反式TBBT-8异构体以溶液结晶微带和薄膜的形式自组织成完全不同的堆积方式。产生的电荷传输性质在很大程度上取决于顺/反噻吩的构型。值得注意的是，使用syn ‐TBBT-8异构体进行固溶处理的OFETs具有高达10.1 cm ² V ^-1 s ^-1的高空穴迁移率，比抗TBBT-8异构体高一个数量级。这项工作突出了基于噻吩并苯的有机半导体的区域异构分子构型对于开发高性能电子设备的重要性。

更新日期：2017-12-04

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