Stimuli-Responsive Aggregation-Induced Delayed Fluorescence Emitters Featuring the Asymmetric D–A Structure with a Novel Diarylketone Acceptor Toward Efficient OLEDs with Negligible Efficiency Roll-Off

Multifunctional luminescent materials with aggregation-induced delayed fluorescence (AIDF) are capable of suppressing concentration-caused emission quenching and exciton annihilation when used as organic light-emitting diode (OLED) emitters. In this contribution, three stimuli-responsive AIDF luminogens, pipd-BZ-PXZ, pipd-BZ-PTZ, and pipd-BZ-DMAC, featuring a D–A asymmetric framework based on a fused N-heterocycle diarylketone acceptor (imid-azo­[1,2-a]­pyridin-2-yl­(phenyl)­methanone pipd) are designed and synthesized. Interestingly, pipd-BZ-PTZ forms two different kinds of crystals (G-crystal and O-crystal) with distinct intermolecular interactions between pipd moieties. The G-crystal with a looser packing mode presents significant morphology-dependent stimuli-responsive behavior with a shifted emission wavelength of 56 nm. Generated by a strong intramolecular charge transfer effect, pipd-BZ-PXZ and pipd-BZ-PTZ exhibit orange to red emission in solution and neat films. Both nondoped and doped devices are fabricated for comparison. Nondoped devices present moderate performance with external quantum efficiencies and current efficiency that reach 7.04% and 19.86 cd A–1, respectively, and the corresponding efficiency roll off at 1000 cd m–2 is as small as 2.3%, which is among the best records of AIDF-OLEDs with an emission wavelength over 570 nm. Doped devices show better performance with corresponding efficiencies of up to 55.41 cd A–1 and 15.77%.