Molecular engineering of locked alkyl aryl carbonyl-based thermally activated delayed fluorescence emitters via a cascade C-H activation process

• Published in: Chemical science (Cambridge) 2023-05, Vol.14 (19), p.5125-5131
• Main Authors: Zhang, Yunxi, Huang, Zhengmei, Yang, Yudong, Liu, Jiahui, Tian, Yang, Bin, Zhengyang, You, Jingsong
• Format: Article
• Language: English
• Subjects: Activated carbon; Aromatic compounds; Carbonyls; Catalysis; Chemistry; Emitters; Fluorescence; Ketones; Organic light emitting diodes; Power efficiency; Quantum efficiency; Rhodium
• ISSN: 2041-6520; 2041-6539
• DOI: 10.1039/d3sc01298k

While diaryl ketones have drawn tremendous attention for the assembly of carbonyl-based thermally activated delayed fluorescence (TADF) emitters, alkyl aryl ketones are almost ignored. In this work, an efficient rhodium-catalyzed cascade C-H activation process of alkyl aryl ketones with phenylboronic acids has been developed for the concise construction of the α,α-dialkyl/aryl phenanthrone skeleton, which unlocks an opportunity to rapidly assemble a library of structurally nontraditional locked alkyl aryl carbonyl-based TADF emitters. Molecular engineering indicates that the introduction of a donor on the A ring enables the emitters to exhibit better TADF properties than those with a donor on the B ring. 2,6-Bis(9,9-dimethylacridin-10(9 )-yl)-10,10-diphenylphenanthren-9(10 )-one (2,6-DMAC-DPPO) with two donors on the A and B rings gives rise to superior organic light-emitting diode (OLED) performance with maximum external quantum efficiency and power efficiency as high as 32.6% and 123.5 lm W , respectively.