Organic light-Emitting diode based on bis(10-phenylanthracen-9-yl)benzene derivatives with a stable white emission
Graphical abstract
Introduction
Organic light-emitting diodes (OLEDs) have been developed since the pioneering research of Tang and VanSlyke [1] due to the considerable potential regarding to the realization of full-color display and solid-state lighting [2], [3], [4]. The search for efficient white OLEDs has been regarded as one of the especially important issue because they are fundamental components in the realization of both full-color displays and solid-state lighting [5]. A number of examples of the realization of white emission OLEDs exist, whereby two (sky blue and orange emitters) or three (red, green, and blue) emitters are used with proper combination of fluorescent or phosphorescent materials in emitting layer [6]. Recently, many groups report the white OLEDs using a single emitter which could emit a white color using a combination of monomer sky blue and orange emissions from bimolecular recombination states such as excimer, exciplex, electroplex, and electromer [7], [8], [9].
Numerous building blocks such as anthracene [10], [11], [12], fluorene [13], carbazole [14], and pyrene [15] are research subjects in the preparation of different kinds of OLED materials; in particular, anthracene and its derivatives have been extensively studied for their excellent characteristics such as unusual photoluminescent properties, a sound electroluminescent performance, and an easier modification capability. The modifications at the 9- and 10-positions of the anthracene are especially easy, and numerous studies on this concept exist [16].
As part of the continuing efforts in the development of the efficient white OLED emitters, we synthesized two fluorescent materials, 1,3-bis(10-phenylanthracen-9-yl)benzene (1) and 2,6-bis(10-phenylanthracen-9-yl)pyridine (2). Both of these materials consist of two phenylanthracene that are connected through different central moieties such as benzene and pyridine at the 9-position of anthracene. The white emission could be obtained from the device using 1 or 2 as the single emitting material, if the monomeric blue emission of either 1 or 2 could be combined with the orange emission from the bimolecular recombination states (excimer, exciplex, electroplex, and electromer) of 1 or 2. In this paper, we present a device using 1 as an emitting material shows a stable white emission.
Section snippets
Synthesis and characterization
The Suzuki cross-coupling reaction in this study comprised of the following general procedure: 9-Phenylanthracen-10-yl-boronic acid (2.4 mol) and the corresponding aryl bromides such as 1,3-dibromobenzene and 2,6-dibromopyridine (1.0 mol); Pd(PPh3)4 (0.04 mol); aqueous 2.0 M Na2CO3 (10.0 mol); ethanol; and toluene were mixed in a flask and the mixture was refluxed for 4 h. Water was then added to the mixture to quench the reaction upon its completion. After cooling, the crude solid was collected by
Results and discussion
The chemical structures and synthetic routes of 1 and 2 are outlined in Scheme 1. These materials were synthesized using Pd-catalyzed Suzuki cross-coupling reactions between 9-Phenylanthracen-10-yl-boronic acid and the corresponding aryl bromides with moderate yields. All the compounds were characterized by 1H NMR, IR, mass spectroscopy, and Element analysis. High-performance liquid chromatography was performed to check the purity of the materials, revealing that their purity was at least above
Conclusion
In conclusion, we used the Suzuki cross-coupling reaction to successfully synthesize two fluorescent materials based on bis(10-phenylanthracen-9-yl)benzene. An OLED device using 1,3-bis(10-phenylanthracen-9-yl)benzene (1) showed a stable white emission at 7 V with CIE coordinates of (0.31, 0.44). This device showed the luminous, power, and external quantum efficiency values of 1.95 cd/A, 0.97 lm/W, and 0.93% at 20 mA/cm2, respectively; furthermore, this device exhibited the stable white emission
Acknowledgments
This research was supported by the Samsung Display and Basic Science Research Program through the NRF funded by the Ministry of Education, Science and Technology, South Kores (NRF-2013R1A1A2A10008105).
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