Modular Nitrogen‐Doped Concave Polycyclic Aromatic Hydrocarbons for High‐Performance Organic Light‐Emitting Diodes with Tunable Emission Mechanisms. Issue 27 (5th May 2022)

• Record Type: Journal Article
• Authors: Wagner, Jakub; Zimmermann Crocomo, Paola; Kochman, Michał Andrzej; Kubas, Adam; Data, Przemysław; Lindner, Marcin
• Is Part Of: Angewandte Chemie international edition. Volume 61:Issue 27(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-05-05
• Subjects: Nitrogen Doping -- Organic Light-Emitting Diodes -- Polycyclic Aromatic Hydrocarbons -- Room-Temperature Phosphorescence -- Thermally Activated Delayed Fluorescence; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.202202232
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: 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. Abstract : Curved and fully conjugated N‐pyrrolic polycyclic aromatic hydrocarbons (N‐PAHs) were utilized as efficient emitters in thermally activated delayed fluorescence organic light‐emitting diode (TADF/OLED) devices. The curvature increases the spatial separation between the highest occupied and lowest unoccupied molecular orbitals, leading to low singlet–triplet gaps, which are essential for high reverse intersystem crossing rates. The overall photoluminescence quantum yield (PLQY) is up to 86 %.