An N-phenylbenzimidazole constrained in a coplanar fashion with a methylene tether (IMAC) was designed and used to prepare a series of emitters exhibiting thermally activated delayed fluorescence (TADF). Four novel TADF emitters using 9,9-dimethylacridine, phenoxazine, phenothiazine, and bis­(di-p-tolylamino)­carbazole as the donor group were designed and synthesized using IMAC as the acceptor. Additionally, two deep-blue fluorescent emitters were prepared with carbazole and tercarbazole as the donor moieties. The twisted conformation between donor and acceptor in these molecules resulted in effective spatial separation of the HOMO and LUMO and small singlet–triplet energy gaps. Crystallographic properties, electronic structures, thermal stabilities, photophysical properties, and energy levels were studied systematically. Ultimately, these findings provide a promising opportunity for the design and synthesis of highly efficient TADF materials based on IMAC derivatives.

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