Thionation Enhances the Electron Mobility of Perylene Diimide for High Performance n-Channel Organic Field Effect Transistors

Tilley Andrew J.; Guo Chang; Miltenburg Mark B.; Schon Tyler B.; Yan Han; Li Yuning; Seferos Dwight S.

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Thionation Enhances the Electron Mobility of Perylene Diimide for High Performance n-Channel Organic Field Effect Transistors

机译：硫离子化可提高高性能n沟道有机场效应晶体管的Per二酰亚胺的电子迁移率

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Perylene diimides (PDIs) are one of the most widely studied n-type materials, showing great promise as electron acceptors in organic photovoltaic devices and as electron transport materials in n-channel organic field effect transistors. Amongst the well-established chemical modification strategies for increasing the electron mobility of PDI, substitution of the imide oxygen atoms with sulfur, known as thionation, has remained largely unexplored. In this work, it is demonstrated that thionation is a highly effective means of enhancing the electron mobility of a bis-N-alkylated PDI derivative. Successive oxygen-sulfur substitution increases the electron mobility such that the fully thionated derivative (S4) has an average mobility of 0.16 cm(2) V-1 s(-1). This is two orders of magnitude larger than the nonthionated parent compound (P), and is achieved by solution deposition and without thermal or solvent vapor annealing. A combination of atomic force microscopy and 2D wide angle X-ray scattering experiments, together with theoretical modeling of charge transport efficiency, is used to explain the strong positive correlation observed between electron mobility and degree of thionation. This work establishes thionation as a highly effective means of enhancing the electron mobility of PDI, and provides motivation for the development of thionated PDI derivatives for organic electronics applications.

机译：ylene二酰亚胺（PDI）是研究最广泛的n型材料之一，作为有机光伏器件中的电子受体和n通道有机场效应晶体管中的电子传输材料，具有广阔的前景。在提高PDI的电子迁移率的成熟化学修饰策略中，酰亚胺硫原子被硫取代（称为硫磺化）在很大程度上尚未得到开发。在这项工作中，证明了硫磺化是增强双-N-烷基化PDI衍生物的电子迁移率的高效手段。连续的氧硫取代增加了电子迁移率，因此完全亚硫酰化的衍生物（S4）的平均迁移率为0.16 cm（2）V-1 s（-1）。这比非亚硫酰化的母体化合物（P）大两个数量级，并且是通过溶液沉积而无需热退火或溶剂蒸汽退火来实现的。结合使用原子力显微镜和2D广角X射线散射实验以及电荷传输效率的理论模型，可以解释观察到的电子迁移率和硫化程度之间的强正相关性。这项工作将硫磺化确立为增强PDI电子迁移率的高效手段，并为开发用于有机电子应用的亚硫代PDI衍生物提供了动力。

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来源
《Advanced Functional Materials》 |2015年第22期|3321-3329|共9页
作者
Tilley Andrew J.; Guo Chang; Miltenburg Mark B.; Schon Tyler B.; Yan Han; Li Yuning; Seferos Dwight S.;
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作者单位

Univ Toronto, Dept Chem, Lash Miller Chem Labs, Toronto, ON M5S 3H6, Canada;

Univ Waterloo, Dept Chem Engn, Waterloo, ON N2L 3G1, Canada|Univ Waterloo, Waterloo Inst Nanotechnol WIN, Waterloo, ON N2L 3G1, Canada;

Univ Toronto, Dept Chem, Lash Miller Chem Labs, Toronto, ON M5S 3H6, Canada;

Univ Toronto, Dept Chem, Lash Miller Chem Labs, Toronto, ON M5S 3H6, Canada;

Univ Toronto, Dept Chem, Lash Miller Chem Labs, Toronto, ON M5S 3H6, Canada;

Univ Waterloo, Dept Chem Engn, Waterloo, ON N2L 3G1, Canada|Univ Waterloo, Waterloo Inst Nanotechnol WIN, Waterloo, ON N2L 3G1, Canada;

Univ Toronto, Dept Chem, Lash Miller Chem Labs, Toronto, ON M5S 3H6, Canada;

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正文语种 eng
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electron mobility; organic field effect transistors; perylene diimide; thionation;

机译：电子迁移率有机场效应晶体管di二酰亚胺硫化;

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专利

1. Publisher's Note: "Air-stable n-channel organic thin-film transistors with high field-effect mobility based on N, N' -bis(heptafluorobutyl)-3,4:9,10-perylene diimide" [Appl. Phys. Lett. 91, 212107 (2007)] [J] . Joon Hak Oh, Shuhong Liu, Zhenan Bao, Applied Physics Letters . 2008,第4期

机译：出版者的注释：“基于N，N′-双（七氟丁基）-3，4：9，10-per二酰亚胺的具有高场效应迁移率的空气稳定的n沟道有机薄膜晶体管” [Appl。物理来吧91，212107（2007）]
2. Air-stable n-channel organic thin-film transistors with high field-effect mobility based on N,N'-bis(heptafluorobutyl)-3,4:9,10-perylene diimide [J] . Joon Hak Oh, Shuhong Liu, Zhenan Bao, Applied Physics Letters . 2007,第21期

机译：基于N，N'-双（七氟丁基）-3,4：9,10-per二酰亚胺的具有高场效应迁移率的空气稳定型n沟道有机薄膜晶体管
3. Novel self-assembled phosphonic acids monolayers applied in N-channel perylene diimide (PDI) organic field effect transistors [J] . Cheng Heng, Huai Jinyue, Cao Li, Applied Surface Science . 2016,第auga15期

机译：N沟道per二酰亚胺（PDI）有机场效应晶体管中应用的新型自组装膦酸单层
4. HIGH-tf DIELECTRIC PROCESS DEVELOPMENT FOR ENHANCED ELECTRON MOBILITY IN HIGH PERFORMANCE FIELD EFFECT TRANSISTORS [C] . P.D. Kirsch, J. Peterson, J.Gutt, International Conference on Semiconductor Technology . 2005

机译：高性能场效应晶体管中增强电子迁移率的高TF电介质工艺开发
5. New platforms for electronic devices: N-channel organic field-effect transistors, complementary circuits, and nanowire transistors. [D] . Yoo, Byungwook. 2007

机译：电子设备的新平台：N沟道有机场效应晶体管，互补电路和纳米线晶体管。
6. Tailoring the Dielectric Layer Structure for Enhanced Performance of Organic Field-Effect Transistors: The Use of a Sandwiched Polar Dielectric Layer [O] . Shijiao Han, Xin Yang, Xinming Zhuang, 2016

机译：量身定制介电层结构以增强有机场效应晶体管的性能：夹层极性介电层的使用
7. High-Mobility Naphthalene Diimide and Selenophene-Vinylene-Selenophene-Based Conjugated Polymer: n-Channel Organic Field-Effect Transistors and Structure-Property Relationship [O] . Sung Min Jae, Luzio Alessandro, Park Won-Tae, 2016

机译：高迁移率的萘二酰亚胺和硒基-亚乙烯基-硒基的共轭聚合物：n沟道有机场效应晶体管及其结构-性能关系

Thionation Enhances the Electron Mobility of Perylene Diimide for High Performance n-Channel Organic Field Effect Transistors

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