High-efficiency Near Infrared Thermally Activated Delayed Fluorescence Based on Phenazine Acceptor
Received date: 2024-10-17
Online published: 2024-12-27
Supported by
National Key R&D Program of China(2020YFA0714604); National Natural Science Foundation of China(22005184); National Natural Science Foundation of China(62375193); International Science and Technology Innovation Cooperation/Hong Kong, Macao and Taiwan Science and Technology Innovation Cooperation Project of Jiangsu Province(BZ2023053)
Two donor-acceptor-donor (D-A-D) type red thermally activated delayed fluorescence (TADF) materials 10,13- bis(4-(diphenylamino)phenyl)dibenzo[a,c]phenazine-3,6-dicarbonitrile (BzPz-TPA) and 10,13-bis(4-(diphenylamino)phenyl)- dipyrido[3,2-a:2',3'-c]phenazine-11,12-dicarbonitrile (PyPz-TPA) were designed and synthesized with dibenzophenazine and dipyridobenzazine as acceptor units and triphenylamine as donor units respectively. Two cyano groups were introduced into BzPz-TPA and PyPz-TPA to enhance the electron-withdrawing capability of the acceptor unit. Strong donor and acceptor units were introduced into the molecular skeletons of BzPz-TPA and PyPz-TPA, and steric hindrance between D and A units led to a twisted D-A configuration, thus achieving relatively small singlet-triplet energy gaps (ΔEST). In addition, the intramolecular hydrogen bonding interaction between donor and acceptor units can modulate the D-A molecular configuration and the overlap between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO). In the BzPz-TPA molecule, the dihedral angle between the donor and acceptor units is 44°, and there is a twisted configuration between D-A, thereby achieving effective separation of HOMO and LUMO. HOMO is mainly located on the donor unit TPA, while LUMO is mainly located on the acceptor unit. In PyPz-TPA molecule, the dihedral angle between the donor and acceptor units is 52°, and the D-A twisted configuration effectively separates the HOMO and LUMO. The HOMO is mainly on the donor unit TPA, and the LUMO is mainly on the acceptor unit. Since BzPz-TPA and PyPz-TPA have the same donor unit, they have similar HOMO energy levels. Due to the rigid skeleton of two molecules and the smaller ΔEST, the BzPz-TPA is doped into the host material 4,4'-bis(9-carbazole)biphenyl (CBP) and resulted in the maximum external quantum efficiency (EQE) of 7.4% for the organic light-emitting diode (OLED) device emitting at 638 nm. When PyPz-TPA is doped into the host material CBP, the OLED device achieved the maximum EQE of 22.6% at 676 nm emission. Besides, the OLED of PyPz-TPA achieved the maximum EQE of 16.58% and near-infrared luminescence at an emission wavelength of 714 nm.
Jinzhu Ma , Yang Li , Shan Gao , Yue Zhao , Lei Ding , Dongying Zhou , Jian Fan . High-efficiency Near Infrared Thermally Activated Delayed Fluorescence Based on Phenazine Acceptor[J]. Acta Chimica Sinica, 2025 , 83(1) : 17 -24 . DOI: 10.6023/A24100310
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