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1.
Front Chem ; 7: 254, 2019.
Article in English | MEDLINE | ID: mdl-31069215

ABSTRACT

The pyridinecarbonitrile derivative is well known as an acceptor unit in fluorescent materials. However, its use in thermally activated delayed fluorescent (TADF) emitters is very limited compared with its benzenecarbonitrile counterparts. Very recently, we developed a series of 4-pyridinecarbonitrile, so-called isonicotinonitrile derivatives, as a highly efficient sky blue-to-green TADF emitters realizing low-drive-voltage organic light-emitting devices (OLEDs). In this work, we contributed new design and development for three 3-pyridinecarbonitrile-based TADF emitters named 2AcNN, 2PXZNN, and 5PXZNN. Among these emitters, a sky blue emitter, 2AcNN, showed a maximum external quantum efficiency (η ext,max) of 12% with CIE (0.19, 0.36). While green emitters, 5PXZNN and 2PXZNN, realized highly efficient TADF OLEDs with a η ext,max of 16-20%. Introduction of electron-donor moiety into the 2-position of 3-pyridinecarbonitrile contributes a larger overlapping of frontier molecular orbitals (FMOs) and stronger intramolecular charge transfer (ICT) interaction generating efficient TADF emitters.

2.
Chemistry ; 25(30): 7308-7314, 2019 May 28.
Article in English | MEDLINE | ID: mdl-30741443

ABSTRACT

Deep-red to near-infrared (NIR) OLEDs, which yield emission peak wavelengths beyond λ=660 nm, are applicable as unique light sources in plant growth or health monitoring systems. Compared with other visible-spectrum OLEDs, however, research in the field of deep-red OLEDs is not as advanced. In this work, three new types of dibenzofuran-based host materials are developed as n-type exciplex host partners. Combining these with the deep-red iridium complex bis(2,3-diphenylquinoxaline)iridium(dipivaloylmethane) ([(DPQ)2 Ir(dpm)]) and N,N'-di(naphalene-1-yl)-N,N'-diphenylbenzidine (α-NPD) as a p-type exciplex host partner, a highly efficient deep-red OLED can be realized with a maximum external quantum efficiency (ηext,max ) of over 16 % with Comission Internationale de l'Éclairge (CIE) coordinates of (0.71, 0.28). In addition, the effect of the doping concentration and the p/n ratio of the exciplex host on the efficiency and the lifetime of the OLEDs are investigated. Consequently, the optimized device exhibits a ηext,max of over 15 % and a six-time longer lifetime operating at high brightness of 100 cd m-2 compared with other state-of-the-art deep-red OLEDs.

3.
Chem Asian J ; 12(17): 2299-2303, 2017 Sep 05.
Article in English | MEDLINE | ID: mdl-28703482

ABSTRACT

Aromatic difluoroboronated ß-diketone (BF2 DK) derivatives are a widely known class of luminescent organic materials that exhibit high photoluminescent quantum efficiency and unique aggregation-dependent fluorescence behavior. However, there have been only a few reports on their use in solid-state electronic devices, such as organic light-emitting devices (OLEDs). Herein, we investigated the solid-state properties and OLED performance of a series of π-extended BF2 DK derivatives that have previously been shown to exhibit intense fluorescence in the solution state. The BF2 DK derivatives formed exciplexes with a carbazole derivative and exhibited thermally activated delayed fluorescence (TADF) behavior to give orange electroluminescence with a peak external quantum efficiency of 10 % that apparently exceeds the theoretical efficiency limit of conventional fluorescent OLEDs (7.5 %), assuming a light out-coupling factor of 30 %.

4.
Chem Asian J ; 12(6): 648-654, 2017 Mar 16.
Article in English | MEDLINE | ID: mdl-28029223

ABSTRACT

Herein, 9,10-dihydro-9,9-dimethylacridine (Ac) or phenoxazine (PXZ)-substituted isonicotinonitrile (INN) derivatives, denoted as 2AcINN, 26AcINN, and 26PXZINN, were developed as a series of thermally activated delayed fluorescence (TADF) emitters. These emitters showed reasonably high photoluminescence quantum yields of 71-79 % in the host films and high power efficiency organic light-emitting diodes (OLEDs). Sky-blue emitter 26AcINN exhibited a low turn-on voltage of 2.9 V, a high external quantum efficiency (ηext ) of 22 %, and a high power efficiency (ηp ) of 66 lm W-1 with Commission Internationale de l'Eclairage (CIE) chromaticity coordinates of (0.22, 0.45), whereas green emitter 26PXZINN exhibited a low turn-on voltage of 2.2 V, a high ηext of 22 %, and a high ηp of 99 lm W-1 with CIE chromaticity coordinates of (0.37, 0.58). These performances are among the best for TADF OLEDs to date.

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