[en] Aiming to develop efficient blue-emitting thermally activated delayed fluorescence (TADF) compounds, we have designed and synthesized derivatives of the well-known sky-blue emitter 2CzPN that contain electron-accepting phosphine chalcogenide groups to stabilize the HOMO level relative to the pristine compound, thus increasing the HOMO-LUMO gap and blue-shifting the emission wavelength. By cyclic voltammetry, photophysical data and quantum-chemical calculations, it was found that polar solvents and matrices validated the proposed concept, but these trends were not recovered in non-polar media. The suitability of these 2CzPN derivatives in polar matrices for optoelectronic applications was explored with electrochemiluminescence (ECL) by measuring emission delays, radical stability, emission stabilities, emission efficiencies and emission spectra. Some of the 2CzPN derivatives showed an unprecedented delayed onset of the ECL, and delayed rising time to the ECL maximum, as well as long ECL emission decay. All of these mentioned delay times suggest that these luminophores primarily emit via organic long-persistent electrochemiluminescence (OLECL) mechanisms. The derivatization of the donor groups of the emitters affected both the radical stability and the predominant emission mechanism, providing important insight into their potential as emitters in solid-state electroluminescent devices.
Disciplines :
Chemistry
Author, co-author :
Kumar, Shiv; Organic Semiconductor Centre, University of St Andrews, EaStCHEM School of Chemistry, St Andrews, United Kingdom
Tourneur, Pauline; Laboratory for Chemistry of Novel Materials, University of Mons, Mons, Belgium
Adsetts, Jonathan R.; Department of Chemistry, The University of Western Ontario, London, Canada
Wong, Michael Y. ; Organic Semiconductor Centre, University of St Andrews, EaStCHEM School of Chemistry, St Andrews, United Kingdom
Rajamalli, Pachaiyappan ; Organic Semiconductor Centre, University of St Andrews, EaStCHEM School of Chemistry, St Andrews, United Kingdom
Chen, Dongyang; Organic Semiconductor Centre, University of St Andrews, EaStCHEM School of Chemistry, St Andrews, United Kingdom
Lazzaroni, Roberto ; Université de Mons - UMONS > Faculté des Sciences > Service de Chimie des matériaux nouveaux ; Materia Nova, Materials R&D center, Mons, Belgium
Viville, Pascal ; Université de Mons - UMONS > Unités externes > Materia Nova ASBL ; Materia Nova, Materials R&D center, Mons, Belgium
Cordes, David B. ; Organic Semiconductor Centre, University of St Andrews, EaStCHEM School of Chemistry, St Andrews, United Kingdom
Slawin, Alexandra M. Z. ; Organic Semiconductor Centre, University of St Andrews, EaStCHEM School of Chemistry, St Andrews, United Kingdom
Olivier, Yoann ; Université de Mons - UMONS > Faculté des Sciences > Service de Chimie des matériaux nouveaux ; Unité de Chimie Physique Théorique et Structurale (UCPTS) & Laboratoire de Physique du Solide (LPS), University of Namur, Namur Institute of Structured Matter (NISM), Namur, Belgium
Cornil, Jérôme ; Laboratory for Chemistry of Novel Materials, University of Mons, Mons, Belgium
Ding, Zhifeng ; Department of Chemistry, The University of Western Ontario, London, Canada
Zysman-Colman, Eli ; Organic Semiconductor Centre, University of St Andrews, EaStCHEM School of Chemistry, St Andrews, United Kingdom
R400 - Institut de Recherche en Science et Ingénierie des Matériaux R150 - Institut de Recherche sur les Systèmes Complexes
Funders :
Fonds De La Recherche Scientifique - FNRS H2020 Marie Skłodowska-Curie Actions Royal Society Canada Foundation for Innovation Natural Sciences and Engineering Research Council of Canada Engineering and Physical Sciences Research Council
Funding text :
The authors thank Dr Sai Kiran Rajendran for providing PL and TCSPC data of 2CzPN in neat film. SK acknowledges the financial support from European Union's Horizon 2020 research and innovation programme under Marie Skłodowska Curie Individual Fellowship (MCIF; Agreement No. 748430-THF-OLED). P. R acknowledges support from a Marie Skłodowska-Curie Individual Fellowship (No. 749557). We thank the EPSRC UK National Mass Spectrometry Facility at Swansea University for analytical services. The work has been supported in Mons by European Union through the Interreg V initiative France-Wallonie-Vlaanderen project LUMINOPTEX and the Belgian National Fund for Scientific Research (FRS-FNRS). Computational resources were provided by the Consortium des Équipements de Calcul Intensif (CÉCI) funded by F. R. S.-FNRS under Grant 2.5020.11. J. C. is an FNRS research director. Y. O. acknowledges funding by the Fonds de la Recherche Scientifique-FNRS under Grant no F.4534.21 (MIS-IMAGINE). We acknowledge the research support from Natural Sciences and Engineering Research Council Canada (NSERC, DG RGPIN-2013-201697, DG RGPIN-2018-06556, and SPG STPGP-2016-493924), Canada Foundation of Innovation, Ontario Innovation Trust (CFI/OIT, 9040) and Western University. J. R. A. appreciates the Ontario graduate scholarships (2018–2022). EZ-C is a Royal Society Leverhulme Trust Senior Research fellow (SRF\R1\201089). For the purpose of open access, the authors have applied a Creative Commons Attribution (CC BY) license.The authors thank Dr Sai Kiran Rajendran for providing PL and TCSPC data of 2CzPN in neat film. SK acknowledges the financial support from European Union's Horizon 2020 research and innovation programme under Marie Sk?odowska Curie Individual Fellowship (MCIF; Agreement No. 748430-THF-OLED). P. R acknowledges support from a Marie Sk?odowska-Curie Individual Fellowship (No. 749557). We thank the EPSRC UK National Mass Spectrometry Facility at Swansea University for analytical services. The work has been supported in Mons by European Union through the Interreg V initiative France-Wallonie-Vlaanderen project LUMINOPTEX and the Belgian National Fund for Scientific Research (FRS-FNRS). Computational resources were provided by the Consortium des ?quipements de Calcul Intensif (C?CI) funded by F. R. S.-FNRS under Grant 2.5020.11. J. C. is an FNRS research director. Y. O. acknowledges funding by the Fonds de la Recherche Scientifique-FNRS under Grant no F.4534.21 (MIS-IMAGINE). We acknowledge the research support from Natural Sciences and Engineering Research Council Canada (NSERC, DG RGPIN-2013-201697, DG RGPIN-2018-06556, and SPG STPGP-2016-493924), Canada Foundation of Innovation, Ontario Innovation Trust (CFI/OIT, 9040) and Western University. J. R. A. appreciates the Ontario graduate scholarships (2018-2022). EZ-C is a Royal Society Leverhulme Trust Senior Research fellow (SRF\R1\201089). For the purpose of open access, the authors have applied a Creative Commons Attribution (CC BY) license.
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