Molecular Design Strategy of Thermally Activated Delayed Fluorescent Emitters Using CN‐Substituted Imidazopyrazine as a New Electron‐Accepting Unit

• Published in: Chemistry, an Asian journal an Asian journal, 2020-01, Vol.15 (1), p.122-128
• Main Authors: Kothavale, Shantaram, Lee, Kyung Hyung, Lee, Jun Yeob
• Format: Article
• Language: English
• Subjects: acceptor; Chemistry; Diodes; efficiency; Emitters; Emitters (electron); Energy gap; Energy management; Fluorescence; imidazopyrazine; Molecular orbitals; OLEDs; Organic light emitting diodes; Phosphorescence; Quantum efficiency; Substitutes; TADF
• ISSN: 1861-4728; 1861-471X
• DOI: 10.1002/asia.201901311

Thermally activated delayed fluorescence (TADF)‐based organic light‐emitting diodes (OLEDs) have attracted enormous attention recently due to their capability to replace conventional phosphorescent organic light‐emitting diodes for practical applications. In this work, a newly designed CN‐substituted imidazopyrazine moiety was utilized as an electron‐accepting unit in a TADF emitter. Two TADF emitters, 8‐(3‐cyano‐4‐(9,9‐dimethylacridin‐10(9H)‐yl)phenyl)‐2‐phenylimidazo[1,2‐a]pyrazine‐3‐carbonitrile (Ac‐CNImPyr) and 8‐(3‐cyano‐4‐(10H‐phenoxazin‐10‐yl)phenyl)‐2‐phenylimidazo[1,2‐a]pyrazine‐3‐carbonitrile (PXZ‐CNImPyr), were developed based on the CN‐substituted imidazopyrazine acceptor combined with acridine and phenoxazine donor, respectively. A CN‐substituted phenyl spacer was introduced between the donor and acceptor for a sufficiently small singlet‐triplet energy gap (ΔEST) and molecular orbital management. Small ΔEST of 0.07 eV was achieved for the phenoxazine donor‐based PXZ‐CNImPyr emitter. As a result, an organic light‐emitting diode based on the PXZ‐CNImPyr emitter exhibited a high external quantum efficiency of up to 12.7 %, which surpassed the EQE limit of common fluorescent emitters. Hence, the CN‐modified imidazopyrazine unit can be introduced as a new acceptor for further modifications to develop efficient TADF‐based OLEDs. A molecular design strategy utilizing imidazopyrazine as new electron‐accepting unit for two thermally activated delayed fluorescence (TADF) emitters (Ac‐CNImPyr and PXZ‐CNImPyr) is proposed. Especially, the TADF emitter with a strong phenoxazine donor (PXZ‐CNImPyr) exhibited sufficiently small ΔEST to initiate the RISC process and realize a high external quantum efficiency of up to 12.7 %.