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Effect of the electron-accepting centre and solubilising substituents on the redox, spectroscopic and electroluminescent properties of four oxadiazoles and a triazole disubstituted with bithiophene

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Abstract

Five and six heterocycle ring assemblies, comprising triazole or oxadiazole acceptor (A) units and thiophene or alkylthiophene donor (D) units in a DDADD and DDAADD arrangement, have been synthesised and characterised by spectroscopic and electrochemical means. It is demonstrated that the replacement of a weaker acceptor (triazole) by a stronger one (oxadiazole) in DDADD compounds results in lowering of the frontier molecular energy gap by 70 meV from 2.94 to 2.87 eV. For oxadiazole-centred compounds these gaps can be further lowered by increasing the number of A units and alkyl solubilising substituents, down to 2.76 eV for the DDAADD compound containing four alkyl pendants. The photoluminescence quantum yield exceeds 50 % for DDADD compounds and reaches 78 % for DDAADD ones. All compounds, when dispersed in a blend consisting of 70 % poly(vinylcarbazole) (PVK) and 30 % of 2-tert-butylphenyl-5-biphenyl-1,3,4-oxadiazole (PBD) (host–guest configuration), demonstrate light-emitting diode behaviour, affording blue, tuneable emission with luminances reaching 120 cd m−2 and luminous efficiencies of 0.12 cd A−1 for non-optimised devices.

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Acknowledgements

A. S. Fisyuk and A. S. Kostuchenko acknowledge partial financial support from the Russian Foundation for Basic Research (15-43-04313-Sibiria-a) and the Ministry of Education and Science of the Russian Federation (Project 2596). M. Zagorska and A. Pron acknowledge partial financial support from Warsaw University of Technology. G. Wiosna-Salyga acknowledges the financial support of the Polish National Science Centre Grant No 2012/04/S/ST4/00128. A. Kurowska and W. Domagala acknowledge the support of Polish National Science Centre Grant No 2011/03/D/ST5/06042. R. Grykien thanks for financial support of his research by Polish National Science Centre grant awarded by Decision No DEC-2011/03/D/ST5/06074 and Master/Mistrz subsidy from the Foundation for Polish Science (9./2013).

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    Authors and Affiliations

    1. Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira av. 55A, Omsk, Russian Federation, 644077

      Anastasia S. Kostyuchenko & Alexander S. Fisyuk

    2. Laboratory of New Organic Materials, Omsk State Technical University, Mira av. 11, Omsk, Russian Federation, 644050

      Anastasia S. Kostyuchenko & Alexander S. Fisyuk

    3. Department of Molecular Physics, Technical University of Lodz, Zeromskiego 116, 90-924, Lodz, Poland

      Gabriela Wiosna-Salyga, Beata Luszczynska, Remigiusz Grykien & Ireneusz Glowacki

    4. Department of Physical Chemistry and Technology of Polymers, Silesian University of Technology, Marcina Strzody 9, 44-100, Gliwice, Poland

      Aleksandra Kurowska & Wojciech Domagala

    5. Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664, Warsaw, Poland

      Malgorzata Zagorska & Adam Pron

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    1. Anastasia S. Kostyuchenko
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    Correspondence to Alexander S. Fisyuk, Wojciech Domagala or Adam Pron.

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    Anastasia S. Kostyuchenko and Gabriela Wiosna-Salyga contributed equally to this article.

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    Kostyuchenko, A.S., Wiosna-Salyga, G., Kurowska, A. et al. Effect of the electron-accepting centre and solubilising substituents on the redox, spectroscopic and electroluminescent properties of four oxadiazoles and a triazole disubstituted with bithiophene. J Mater Sci 51, 2274–2282 (2016). https://doi.org/10.1007/s10853-015-9529-4

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