Modular Nitrogen-Doped Concave Polycyclic Aromatic Hydrocarbons for High-Performance Organic Light-Emitting Diodes with Tunable Emission Mechanisms

Although bowl-shaped N-pyrrolic polycyclic aromatic hydrocarbons (PAHs) can achieve excellent electron-donating ability, their application for optoelectronics is hampered by typically low photoluminescence quantum yields (PLQYs). To address this issue, we report the synthesis and characterization of a series of curved and fully conjugated nitrogen-doped PAHs. Through structural modifications to the electron-accepting moiety, we are able to switch the mechanism of luminescence between thermally activated delayed fluorescence (TADF) and room-temperature phosphorescence (RTP), and to tune the overall PLQY in the range from 9 % to 86 %. As a proof of concept, we constructed solid-state organic light-emitting diode (OLED) devices, which has not been explored to date in the context of concave N-doped systems being TADF/RTP emitters. The best-performing dye, possessing a peripheral trifluoromethyl group adjacent to the phenazine acceptor, exhibits yellow to orange emission with a maximum external quantum efficiency (EQE) of 12 %, which is the highest EQE in a curved D-A embedded N-PAH to date.

Automated summary

In this study, the synthesis and characterization of curved and fully conjugated nitrogen-doped PAHs were reported. By modifying the structure of the electron-accepting moiety, the luminescence mechanism was switched between TADF and RTP, and the overall PLQY was tuned in the range of 9% to 86%. Solid-state OLED devices were constructed, achieving a high external quantum efficiency.