[2.2]Paracyclophane-Substituted Chiral Multiresonant Thermally Activated Delayed Fluorescence Emitters for Efficient Organic Light-Emitting Diodes

We report two pairs of chiral multi-resonant thermally activated delayed fluorescence (MR-TADF) materials PCP-DiKTa and Czp-DiKTa by decorating a known MR-TADF core, DiKTa, with different [2.2]paracyclophane (PCP) based planar chiral groups. PCP-DiKTa shows narrow sky-blue emission with a full width at half maximum (FWHM) of 44 nm, while the emission of Czp-DiKTa is slightly broader with a FWHM of 66 nm and red-shifted. Both emitters show high photoluminescence quantum yields of 93 and 99% for PCP-DiKTa and Czp-DiKTa, respectively. Enantiomerically pure samples of both compounds show chiroptical properties in the ground state while only Czp-DiKTa exhibited chiroptical activity in the excited state, with dissymmetry factors (|gPL|) of 4×10-4. Organic light-emitting diodes (OLEDs) with PCP-DiKTa and Czp-DiKTa showed maximum external quantum efficiencies (EQEmax) of 25.7 and 29.2%, with EL of 489 and 518 nm, and FWHMs of 53 and 69 nm, respectively. These EQEmax values are higher than those of other reported devices employing PCP-based D-A type emitters. Our work demonstrates that the PCP moiety is not only a powerful building block to develop planar chiral emitters but one that is compatible with the fabrication of high efficiency devices.