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Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
Published on: October 24, 2017
Utilization of Multi-Heterodonors in Thermally Activated Delayed Fluorescence Molecules and Their High Performance
Umamahesh Balijapalli1, Masaki Tanaka1, Morgan Auffray1
1Center for Organic Photonics and Electronics Research (OPERA) , Kyushu University , 744 Motooka , Nishi, Fukuoka 819-0395 , Japan.
Abstract:
We report a series of pentacarbazolyl-benzonitrile derivatives such as 2,4,6-tri(9H-carbazol-9-yl)-3,5-bis(3,6-di(pyridin-3-yl)-9H-carbazol-9-yl)benzonitrile (mPyBN), 3,5-bis(3,6-bis(4-(trifluoromethyl)phenyl)-9H-carbazol-9-yl)-2,4,6-tri(9H-carbazol-9-yl)benzonitrile (pCF3BN), 2,4,6-tri(9H-carbazol-9-yl)-3-(3,6-di(pyridin-3-yl)-9H-carbazol-9-yl)-5-(3,6-diphenyl-9H-carbazol-9-yl)benzonitrile (PyPhBN), 3-(3,6-bis(4-(trifluoromethyl)phenyl)-9H-carbazol-9-yl)-2,4,6-tri(9H-carbazol-9-yl)-5-(3,6-di(pyridin-3-yl)-9H-carbazol-9-yl)benzonitrile (PyCF3BN), and 3-(3,6-bis(4-(trifluoromethyl)phenyl)-9H-carbazol-9-yl)-2,6-di(9H-carbazol-9-yl)-5-(3,6-di(pyridin-3-yl)-9H-carbazol-9-yl)-4-(9H-pyrido[3,4-b]indol-9-yl)benzonitrile (CbPyCF3BN) in which some of the carbazoles are substituted with modified 3,5-diphenyl carbazoles, exhibiting thermally activated delayed fluorescence (TADF) properties. These emitters comprised two, three, and four different types of donors, capable of bluish-green emission of around 480 nm with relatively high photoluminescence quantum yields over 90% in solution. Emitters, namely, PyPhBN, PyCF3BN, and CbPyCF3BN, composed of three and four different types of donors endowed a rather short delayed lifetime (τd) of 4.25, 5.01, and 3.65 μs in their film state, respectively. Bluish-green organic light-emitting diodes based on PyPhBN, PyCF3BN, and CbPyCF3BN exhibit a high external quantum efficiency of 20.6, 19.5, and 19.6%, respectively, with unsurpassed efficiency roll-off behavior. These results indicate that the TADF properties of multidonor type molecules can be manipulated by controlling the types and number of electron donor units.
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