Fluorinated dibenzo[a,c]-phenazine-based green to red thermally activated delayed fluorescent OLED emitters

Purely organic thermally activated delayed fluorescence (TADF) emitting materials for organic light-emitting diodes (OLEDs) enable a facile method to modulate the emission color through judicious choice of donor and acceptor units. Amongst purely organic TADF emitters, the development of TADF molecules that emit at longer wavelengths and produce high-efficiency devices that show low efficiency roll-off remains a challenge. We report a modular synthesis route that delivers three structurally related fluorinated dibenzo[a,c]-phenazine-based TADF molecules, each bearing two donor moieties with different electron-donating strengths, namely 3,6-bis(3,6-di-tert-butyl-9H-carbazol-9-yl)-10-fluorodibenzo[a,c]phenazine (2DTCz-BP-F), 3,6-bis(9,9-dimethylacridin-10(9H)-yl)-10-fluorodibenzo[a,c]phenazine (2DMAC-BP-F) and 10,10'-(10-fluorodibenzo[a,c]phenazine-3,6-diyl)bis(10H-phenoxazine) (2PXZ-BP-F). They exhibit donor strength-controlled color-tuning over a wide color range from green to deep-red with photoluminescence maxima, λ_PL, of 505 nm, 589 nm, and 674 nm in toluene solution. OLED devices using these TADF materials showed excellent to moderate performance with an EQE_max of 21.8% in the case of 2DMAC-BP-F, 12.4% for 2PXZ-BP-F and 2.1% with 2DTCZ-BP-F, and associated electroluminescence (EL) emission maxima, λ_EL, of 585 nm, 605 nm and 518 nm in an mCBP host, respectively.