Avoiding Energy Loss on TADF Emitters: Controlling the Dual Conformations of D–A Structure Molecules Based on the Pseudoplanar Segments

Abstract

The recent introduction of thermally activated delayed fluorescence (TADF) emitters is regarded as an important breakthrough for the development of high efficiency organic light-emitting devices (OLEDs). The planar D and A groups are generally used to construct TADF emitters for their rigid structure and large steric hindrance. In this work, it is shown that many frequently used nonaromatic (noncontinuous conjugation or without satisfying Hückel's rule) planar segments, such as 9,9-dimethyl-9,10-dihydroacridine, are actually pseudoplanar segments and have two possible conformations–a planar form and a crooked form. Molecules constructed from pseudoplanar segments can thus have two corresponding conformations. Their existence can have significant impact on the performance of many TADF emitters. Two design strategies are presented for addressing the problem by either (1) increasing the rigidity of these groups to suppress its crooked form or (2) increasing the steric hindrance of the linked group to minimize energy of the emitters with the highly twisted form. Following these strategies, two new emitters are synthesized accordingly and successfully applied in OLEDs demonstrating high external quantum efficiencies (20.2% and 18.3%).

A schematic energy level diagram of (2-(9,9-dimethylacridin-10(9H)-yl) thianthrene-5,5,10,10-tetraoxide) shows that molecules constructed from pseudoplanar segments can have two corresponding conformations, which have significant impact on the performance of many thermally activated delayed fluorescence emitters. By either increasing the rigidity of these groups, or by increasing the steric hindrance of the linked group, the problem can be addressed.

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