Diversity-Oriented Synthesis of Diaza-Polycyclic Aromatic Hydrocarbons Coupled with Virtual Screening for OLED Applications

The development of organic light-emitting diode (OLED) materials requires precisely engineered molecular architectures with tailored optoelectronic properties. Here, we present a strategy that synergistically integrates diversity-oriented synthesis (DOS) with virtual screening to systematically explore the chemical space of diaza-polycyclic aromatic hydrocarbons (diaza-PAHs) for OLED applications. DOS, originally developed for drug discovery, serves as a powerful tool to generate structurally diverse molecular libraries, granting access to previously unexplored diaza-PAHs with potential OLED functionality. Complementing this synthetic approach, virtual screening enables the rapid identification of optimal candidates from an extensive library of computationally generated structures, thereby streamlining the material discovery process. In this work, we introduce a rhodium-catalyzed method that combines sequential C-H activation and annulation, offering a modular synthetic protocol for diaza-PAH scaffolds with tunable electronic properties. By computationally screening 1,061 core structures, we identified two lead frameworks─2,6-diazaanthracene and 2,8-dipyridylthiophene─as potential prototypes for OLED applications. Guided by these computational insights, we synthesized four diaza-PAH derivatives, which exhibited exceptional performance as electron-transporting and host materials in high-efficiency phosphorescent OLEDs. This integrated experimental and computational approach not only accelerates the identification of functional materials but also significantly reduces experimental time and resource consumption. This paradigm shift underscores the potential of merging synthetic diversity with data-driven molecular discovery to advance optoelectronic materials research.