Issue 5, 2018

6,6′-Diaryl-substituted biazulene diimides for solution-processable high-performance n-type organic semiconductors

Abstract

Azulene, a non-benzenoid aromatic hydrocarbon, is a promising building block for constructing organic optoelectronic materials. Herein, a series of 6,6′-diaryl-substituted biazulene diimides (1–5) are designed and synthesized for solution-processable organic semiconductors. These compounds exhibited excellent electron transport properties with fine-tuned molecular energy levels (HOMO: −5.68 to −6.04 eV; LUMO: −3.63 to −3.73 eV). Bottom-gate-top-contact organic field effect transistors (OFETs) based on compounds 1–3 and 5 displayed unipolar n-type semiconducting properties with optimized average electron mobilities of 0.12–0.45 cm2 V−1 s−1, of which the devices based on 2 demonstrated an electron mobility of up to 0.52 cm2 V−1 s−1, the highest electron mobilities for azulene-based organic semiconductors and also among the highest values for solution-processable n-channel OFETs. Devices based on 4 showed ambipolar FET performance with electron and hole mobilities of 0.31 cm2 V−1 s−1 and 0.029 cm2 V−1 s−1, respectively. The ambipolar charge transport behavior of 4 is due to its higher HOMO energy level (−5.68 eV) than the others (−5.78 to −6.04 eV). The excellent electron transport ability of compounds 1–5 might be attributed to the dense molecular packing induced by the dipolar moment of the azulene units as revealed by single crystal analysis. Besides, compounds 2 and 5 were used as electron acceptors for organic photovoltaic devices, and an average power conversion efficiency of about 1.3% was obtained for their respective blend thin films with electron donor PTB7-Th. The results demonstrate that 6,6′-diaryl-substituted biazulene diimides are promising solution-processable n-type organic semiconductors, and the azulene unit has great potential for constructing excellent organic optoelectronic materials.

Graphical abstract: 6,6′-Diaryl-substituted biazulene diimides for solution-processable high-performance n-type organic semiconductors

Supplementary files

Article information

Article type
Research Article
Submitted
28 Jan 2018
Accepted
06 Mar 2018
First published
07 Mar 2018

Mater. Chem. Front., 2018,2, 975-985

6,6′-Diaryl-substituted biazulene diimides for solution-processable high-performance n-type organic semiconductors

H. Xin, J. Li, C. Ge, X. Yang, T. Xue and X. Gao, Mater. Chem. Front., 2018, 2, 975 DOI: 10.1039/C8QM00047F

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements