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Issue 2, 2014
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Design and synthesis of novel anthracene derivatives as n-type emitters for electroluminescent devices: a combined experimental and DFT study

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Abstract

Six novel anthracene-oxadiazole derivatives, 4a (2-(4-(anthracen-9-yl)phenyl)-5-p-tolyl-1,3,4-oxadiazole), 4b (2-(4-(anthracen-9-yl)phenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole), 4c (2-(4-(anthracen-9-yl)phenyl)-5-(4-methoxyphenyl)-1,3,4-oxadiazole), 8a (2-(4-(anthracen-9-yl)phenyl)-5-m-tolyl-1,3,4-oxadiazole), 8b (2-(3-(anthracen-9-yl)phenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole) and 8c (2-(3-(anthracen-9-yl)phenyl)-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole) have been synthesized and characterized for use as emitters in organic light emitting devices (OLEDs). They show good thermal stability (Td, 297–364 °C) and glass transition temperatures (Tg) in the range of 82–98 °C, as seen from the thermo gravimetric analysis and differential scanning calorimetric studies. The solvatochromism phenomenon and electrochemical properties have been studied in detail using UV-Vis absorption, fluorescence spectroscopy and cyclic voltammetry. TD-DFT calculations have been carried out to understand the electrochemical and photophysical properties. The spatial structures of 4b and 8c are further confirmed by X-ray diffraction analysis. Un-optimized non-doped electroluminescent devices were fabricated using these anthracene derivatives as emitters with the following device configuration: ITO (120 nm)/α-NPD (30 nm)/4a–4c or 8a–8c (35 nm)/BCP (6 nm)/Alq3 (28 nm)/LiF (1 nm)/Al (150 nm). Among all the six compounds, 8a displays the maximum brightness of 1728 cd m−2 and current efficiency 0.89 cd A−1. Furthermore, as an electron transporter, 8a exhibited superior performance (current efficiency is 11.7 cd A−1) than the device using standard Alq3 (current efficiency is 8.69 cd A−1), demonstrating its high potential for employment in OLEDs. These results indicate that the new anthracene-oxadiazole derivatives could play an important role in the development of OLEDs.

Graphical abstract: Design and synthesis of novel anthracene derivatives as n-type emitters for electroluminescent devices: a combined experimental and DFT study

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The article was received on 16 Aug 2013, accepted on 24 Oct 2013 and first published on 25 Oct 2013


Article type: Paper
DOI: 10.1039/C3PP50284H
Photochem. Photobiol. Sci., 2014,13, 342-357

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    Design and synthesis of novel anthracene derivatives as n-type emitters for electroluminescent devices: a combined experimental and DFT study

    G. Mallesham, S. Balaiah, M. A. Reddy, B. Sridhar, P. Singh, R. Srivastava, K. Bhanuprakash and V. J. Rao, Photochem. Photobiol. Sci., 2014, 13, 342
    DOI: 10.1039/C3PP50284H

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