Issue 26, 2020

Benzo[4,5]thieno-S,S-dioxide-[3,2-b]benzofurans: synthesis, properties and application in electroluminescent devices

Abstract

The first mixed thieno-S,S-dioxide-furan acenes (BTOBFs) were constructed by simple oxidation of benzo[4,5]thieno-[3,2-b]benzofurans (BTBFs). After oxidation, the absorption and emission peaks of the compounds undergo a significant red shift, and fluorescence quantum yields (Φf = 0.23–0.90) are increased several to several tens of times thanks to the more rigid and more π-extended molecular backbone as well as significant intramolecular charge transfer. F-BTOBF and F,Cl-BTOBF displayed somewhat low device performance with external quantum efficiency (EQE) of 0.72–0.78% yet desirable blue emission. However, when we introduce strong electron-donating groups such as carbazolyl or triphenylamino group into BTOBFs to further tune the electronic properties, the resulting compounds 2-NPhCz-BTOBF and 2-TPA-BTOBF exhibit not only much red shift in absorption and fluorescence, but also significant improvement in hole mobility. As a result, these two compounds displayed much better device performance with respectable EQEs of 5.82–6.49%, low turn-on voltage less than 3 V and lower efficiency roll-off. Therefore, for the first time, this work reports the huge potential of mixed thieno-S,S-dioxide-furan acenes as blue to green emitters for high-performance OLEDs.

Graphical abstract: Benzo[4,5]thieno-S,S-dioxide-[3,2-b]benzofurans: synthesis, properties and application in electroluminescent devices

Supplementary files

Article information

Article type
Paper
Submitted
12 Dec 2019
Accepted
31 May 2020
First published
02 Jun 2020

J. Mater. Chem. C, 2020,8, 8796-8803

Benzo[4,5]thieno-S,S-dioxide-[3,2-b]benzofurans: synthesis, properties and application in electroluminescent devices

W. Ma, G. Liu, L. Zhou, B. Li and Y. Wang, J. Mater. Chem. C, 2020, 8, 8796 DOI: 10.1039/C9TC06790F

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