BN-embedded nonacene, tridecacene,
and heptadecacene
frameworks
were constructed using one-shot quadruple, sextuple, and octuple borylation
reactions, respectively. The key to success is the judicious choice
of borylating reagents and long-chain alkyl-substituted carbazolyl
groups as boron-trapping groups, which suppressed the decrease in
HOMO energy and insolubilization associated with borylation. Based
on the product yields, each electrophilic C–H borylation proceeded
in >99% yield, which is the best efficiency reported so far for
C–H
borylation reactions. Owing to the multiple resonance effects of boron
and nitrogen, the prepared acenes exhibited ultra-narrowband green
thermally activated delayed fluorescence with full-width at half-maximum
of 12–16 nm; moreover, their k
RISC values were in the order of 105 s–1. We fabricated an organic light-emitting diode by employing the
nonacene as an emitter, which exhibited high external quantum efficiency
(EQE) of 28.7%. The device also showed a minimum efficiency roll-off
with an EQE of 25.8% at 1000 cd m–2.