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Novel D–A chromophores with condensed 1,2,4-triazine system simultaneously display thermally activated delayed fluorescence and crystallization-induced phosphorescence

Maggiore, Antonio; Tan, Xiaofeng; Brosseau, Arnaud; Danos, Andrew; Miomandre, Fabien; Monkman, Andrew P.; Audebert, Pierre; Clavier, Gilles

Novel D–A chromophores with condensed 1,2,4-triazine system simultaneously display thermally activated delayed fluorescence and crystallization-induced phosphorescence Thumbnail


Authors

Antonio Maggiore

Xiaofeng Tan

Arnaud Brosseau

Fabien Miomandre

Pierre Audebert

Gilles Clavier



Abstract

Control of photophysical properties is crucial for the continued development of electroluminescent devices and luminescent materials. Preparation and study of original molecules uncovers design rules towards efficient materials and devices. Here we have prepared 7 new compounds based on the popular donor–acceptor design used in thermally activated delayed fluorescence emitters. We introduce for the first time benzofuro[3,2-e]-1,2,4-triazine and benzothieno[3,2-e]-1,2,4-triazine acceptors which were connected to several common donors: phenoxazine, phenothiazine, carbazole and 3,6-di-tert-butylcarbazole. DFT calculations, and steady-state and time-resolved photophysical studies were conducted in solution and in solid states. While derivatives with azine moieties are non-emissive in any form, the compounds comprising 3,6-di-tert-butylcarbazole display TADF in all cases. More interestingly, the two derivatives substituted with a carbazole donor are TADF active when dispersed in a polymer matrix and phosphorescent at room temperature in neat films (microcrystalline form).

Citation

Maggiore, A., Tan, X., Brosseau, A., Danos, A., Miomandre, F., Monkman, A. P., …Clavier, G. (2022). Novel D–A chromophores with condensed 1,2,4-triazine system simultaneously display thermally activated delayed fluorescence and crystallization-induced phosphorescence. Physical Chemistry Chemical Physics, 24(29), 17770-17781. https://doi.org/10.1039/d2cp00777k

Journal Article Type Article
Acceptance Date Jun 21, 2022
Online Publication Date Jul 4, 2022
Publication Date Aug 7, 2022
Deposit Date Aug 16, 2022
Publicly Available Date Jul 4, 2023
Journal Physical Chemistry Chemical Physics
Print ISSN 1463-9076
Electronic ISSN 1463-9084
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 24
Issue 29
Pages 17770-17781
DOI https://doi.org/10.1039/d2cp00777k

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