Thermal, spectroscopic, electrochemical, and electroluminescent characterization of malononitrile derivatives with triphenylamine structure

Danuta Sęk; Sonia Kotowicz; Sławomir Kula; Mariola Siwy; Agata Szłapa-Kula; Jan Grzegorz Małecki; Sebastian Maćkowski; Ewa Schab-Balcerzak

doi:10.1016/j.saa.2018.11.025

Thermal, spectroscopic, electrochemical, and electroluminescent characterization of malononitrile derivatives with triphenylamine structure

Spectrochim Acta A Mol Biomol Spectrosc. 2019 Mar 5:210:136-147. doi: 10.1016/j.saa.2018.11.025. Epub 2018 Nov 13.

Authors

Danuta Sęk¹, Sonia Kotowicz², Sławomir Kula², Mariola Siwy¹, Agata Szłapa-Kula², Jan Grzegorz Małecki², Sebastian Maćkowski³, Ewa Schab-Balcerzak⁴

Affiliations

¹ Centre of Polymer and Carbon Materials, Polish Academy of Sciences, 34 M. Curie-Sklodowska Str., 41-819 Zabrze, Poland.
² Institute of Chemistry, University of Silesia, 9 Szkolna Str., 40-006 Katowice, Poland.
³ Institute of Physics, Faculty of Physics, Astronomy and Informatics, Nicolaus Copernicus University, 5 Grudziadzka Str., 87-100 Torun, Poland.
⁴ Centre of Polymer and Carbon Materials, Polish Academy of Sciences, 34 M. Curie-Sklodowska Str., 41-819 Zabrze, Poland; Institute of Chemistry, University of Silesia, 9 Szkolna Str., 40-006 Katowice, Poland. Electronic address: ewa.schab-balcerzak@us.edu.pl.

PMID: 30453189
DOI: 10.1016/j.saa.2018.11.025

Abstract

Three push-pull molecules with linear, quadrupolar and tripodal arrangements, consisting of triphenylamine (electro-donor) substituted with malononitrile groups (electro-acceptor), were synthesized with high yield by a simple procedure. Impact of the number of malononitrile substituents on optoelectronic properties was investigated with cyclic voltammetry, absorption and emission spectroscopy, as well as density functional theory calculation. The derivatives formed amorphous materials and exhibited low energy band gaps ranging from 2.06 to 2.49 eV. UV-Vis absorption and photoluminescence emission spectra were investigated in solutions (CHCl₃, NMP) and in solid-state as thin films and two kinds of blends (with PMMA and PVK:PBD). Quantum yield of photoluminescence was dependent on the molecule structure, solvent, and solid-state layer formulation. The compounds exhibited high photoluminescence quantum yield in the range of 15-42% and 12-59% in solid-state as film and blend with PMMA (1 wt%), respectively, being promising for applications in light emitting diodes. The diodes with active layer consisting of neat derivatives and compounds molecularly dispersed in PVK:PBD (50:50 wt%) matrix showed orange and green electroluminescence.

Keywords: Electrochemistry; Electroluminescence; Malononitrile; Photoluminescence; Triphenylamine.