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Phosphonate functionalized oxadiazole derivative as an efficient electron transporting material for solution-processed blue electrophosphorescent devices

Jianhong Lü, Zhihua Ma, Bin Meng, Dan Sui, Baohua Zhang, Zhiyuan Xie, Xiabin Jing, Fosong Wang, Junqiao Ding, and Lixiang Wang

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Abstract

An efficient electron transporting material, P-OXD (1,3-bis[(4-(4-diethylphosphoryl-butyl-phenyl))-1,3,4-oxidiazol-2-yl]phenylene), has been synthesized and thoroughly characterized. Due to its alcohol-soluble nature, P-OXD can be spin-coated atop the light emitting layer to form high quality film without dissolving the underlying layer. As a consequence, the double-layer blue electrophosphorescent device has been successfully fabricated, giving a peak luminous efficiency of 10.5 cd/A, and a maximum brightness of 8200 cd/m2 with the Commission Internationale de L’Eclairage (CIE) coordinates of (0.16, 0.33). The promising results indicate that P-OXD has a potential application in solution-processed multilayer polymer light-emitting diodes.

©2011 Optical Society of America

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Figures (5)
Fig. 1
Fig. 1 Design strategy of alcohol-soluble electron transporting material P-OXD.

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Fig. 2
Fig. 2 , Synthesis of the alcohol-soluble electron transporting material P-OXD. Reagents and conditions: i) Mg/I2, THF, 70 °C, 2h; B(OCH3)3, −78 °C; HCl (aq.) ii) Methyl 4-bromobenzoate, Pd(dppf)Cl2·CH2Cl2, K2CO3, Ag2O, THF, 70 °C, 16h; iii) NH2NH2·H2O, 120 °C, 24h; iv) Isophthaloyl dichloride, Et3N, NMP, 35 °C, 5h; v) POCl3, 120 °C, 18h; vi) BBr3, DCM, 0 °C→r.t., 24h; vii) P(OEt)3, 180 °C, 16h.

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Fig. 3
Fig. 3 The comparison of absorption (10−5M in DCM) and fluorescent (10−5M in Toluene) spectra at room temperature as well as phosphorescent spectra (in Toluene) at 77K between OXD-7 and P-OXD.

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Fig. 4
Fig. 4 The electrochemical curves of P-OXD and OXD-7 measured in THF (Scan rate: 100 mV s−1).

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Fig. 5
Fig. 5 The current density-voltage (a) brightness–voltage (b), and luminous efficiency versus current density (c) characteristics for device A (solid squares), device B (empty circles), device C (empty squares) and device D (solid circles). d) The EL spectrum for device D. Inset: The AFM height image of the P-OXD film spin-coated on top of the emitting layer.

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Tables (1)

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Table 1 The EL Properties of the Devices

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