INVESTIGATION OF NEW TADF MATERIALS DERIVATIVE OF THE 1,3,5-TRIAZINE MOLECULE

Eyad Al Souki1, 2, Ikbal Marghad2, Mathieu Sauthier1

1 Univ. Lille, CNRS, Centrale Lille, Univ. Artois, UMR 8181, UCCS, Unité de Catalyse et Chimie du Solide, F-59000, Lille, France.

2 LABKICOSMOS, École Centrale de Lille, 1 Av. Paul Langevin, 59650 Villeneuve-d'Ascq, France.

[email protected]

Thermally activated delayed fluorescence (TADF) properties, which enable the harvesting of light from both singlet and triplet excitons without the use of any noble heavy metals, are of interest for a wide range of applications. These materials are now considered the third generation of OLED materials [1]. Among such emitters, the 1,3,5-triazine TADF derivatives can be synthesized using the 2,4,6-tris (4-fluorophenyl)-1,3,5-triazine a cost-effective intermediate developed by the company «LABKICOSMOS». Through tri-substitution of the fluoride, the 1,3,5-triazine moiety is decorated with carbazole, phenothiazine, phenoxazine, diphenylamine, and 3-methyl indole donors, yielding donor-acceptor type compounds with the TADF effect [2, 3]. Our second goal was to create a new series of molecules derived from 1,3,5-triazine. To the best of our knowledge, the mono- and di-substitution of the 2,4,6-tris (4-fluorophenyl)-1,3,5-triazine intermediate has never been investigated. This work is focused on a new series of 1,3,5-triazine TADF derivatives through the mono- and di-substitution of our intermediate. The study of the TADF effect and the efficiency of this new series is still in progress.

The presentation describes the synthesis of the tri-substituted derivatives as well as the first results concerning the selective synthesis of mono- and di-substituted derivatives.

Figure 1
Fig. 1. Synthetic route to new triazine derivatives from the intermediate molecule.

[1] Uoyama, H., Goushi, K., Shizu, K. et al. Highly efficient organic light-emitting diodes from delayed fluorescence. Nature 492, 234–238 (2012).

[2] Marghad, I; Bencheikh, F; Wang, C; Manolikakes, S; Rérat, A; Gosmini, C; Kim, D.H; Ribierre, J-C; Adachi, C. RSC Adv., 2019, 9, 4336-4343.

[3] Marghad, I; Kim, D. H; Tian, X; Mathevet, F; Gosmini, C; Ribierre, J-C; Adachi, C. ACS Omega, 2018, 3, 2254-2260.