A deep-red fluorophore based on naphthothiadiazole as emitter with hybridized local and charge transfer and ambipolar transporting properties for electroluminescent devices

Herein, we report the synthesis and characterization of an efficient ambipolar charge-carrier-transporting deep-red fluorophore (TPECNz) based on a donor–acceptor–donor (D–A–D)-type molecule and its application as a non-doped emitter in an organic light-emitting diode (OLED). The fluorophore TPECNz contains naphtho[2,3-c][1,2,5]thiadiazole (Nz) as a strong acceptor unit symmetrically functionalized with N-(4-(1,2,2-triphenylvinyl)phenyl)carbazole as a donor and aggregation-induced emission (AIE) luminogen. The experimental (solvatochromic and emission in THF/water mixtures studies) and theoretical investigations prove that TPECNz retains cooperative hybridized local and charge transfer (HLCT) and weak AIE features. Thanks to its D–A–D-type structure with a proper twist angle between the D and A units, a strong electron deficiency of the Nz unit, and electron-donating and hole-transporting natures of carbazole, TPECNz exhibits a strong deep red emission (λ_em = 648 nm) with a high fluorescence quantum yield of 96%, outstanding thermal property (T_g = 236 °C), and ambipolar charge-carrier-transporting property with a decent balance of mobility of electrons (1.50 × 10⁻⁵ cm² V⁻¹ s⁻¹) and holes (4.42 × 10⁻⁶ cm² V⁻¹ s⁻¹). TPECNz is successfully employed as a non-doped emitter in an OLED which displays deep red electroluminescent emission peaked at 659 nm with CIE coordinates of (0.664, 0.335)), an EQE_max of 3.32% and exciton utilization efficiency (EUE) of 47%.

Beilstein J. Org. Chem. 2023, 19, 1664–1676. doi:10.3762/bjoc.19.122