Unlocking Structurally Nontraditional Naphthyridine-Based Electron-Transporting Materials with C-H Activation-Annulation.

Abstract

The inherent benefits of C-H activation have given rise to innovative approaches in designing organic optoelectronic molecules that depart from conventional methods. While theoretical calculations have suggested the suitability of the 2,6-naphthyridine scaffold for electron transport materials (ETMs) in organic light-emitting diodes (OLEDs), the existing synthetic methodologies have proven to be insufficient for the construction of multiple arylated and fully aryl-substituted molecules. Herein, we present a solution for the synthesis of 2,6-naphthyridine derivatives, with the rhodium-catalyzed consecutive C-H activation-annulation process of fumaric acid with alkynes standing as the pivotal step within this strategy. The ETMs, purposefully designed and synthesized based on the 2,6-naphthyridine framework, exhibit an impressively high glass-transition temperature (Tg) of 282 °C and high electron mobility (μe), setting a new benchmark for ETMs in OLEDs with a μe exceeding 10-2 cm2 V-1 s-1. These materials prove to be versatile ETM candidates suitable for red, green, and blue phosphorescent OLED devices.