Construction of biomass-based AIEgens with dehydroabietic acid triarylamine and tetraphenylethene Moieties for non-doped OLEDs. (27th August 2022)

• Record Type: Journal Article
• Authors: Gao, Yanan; Zhang, Xinwen; Song, Jie; Dou, Liwei; Gao, Hong; Shang, Shibin; Song, Zhanqian
• Is Part Of: Tetrahedron. Volume 121(2022)
• Publication Date: 2022-08-27
• Subjects: Natural rosin -- Dehydroabietic acid triarylamine (DTPA) -- Tetraphenylethene (TPE) -- Aggregation-induced emission luminogens (AIEgens) -- Non-doped organic light-emitting diodes (OLEDs); Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2022.132922
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Dehydroabietic acid triarylamine (DTPA) synthesized from renewable natural rosin is an excellent hole-transporting material but is affected by aggregation-caused quenching in the solid state. Herein, two new biomass-based AIE luminogens (AIEgens), namely DTPA-TPE and 2DTPA-TPE, were synthesized through the attachment of DTPA to tetraphenylethene (TPE). Their aggregates in poor solvents and thin films have a strong emission with a fluorescence quantum yield of up to 67.4%. DTPA AIEgens exhibit superior thermal and morphological stability, showing high thermal degradation ( T 5d up to 412.0 °C) and glass transition ( T g up to 150.8 °C) temperatures. Electroluminescence (EL) devices with compounds used either as emitting layers (EMLs) or as EMLs and hole-transporting layers (HTLs) were constructed. The device with 2DTPA-TPE as the EML exhibits the best performance (turn-on voltage of 2.4 V, maximum luminance of 12, 414 cd m −2, current efficiency of 6.2 cd A −1, and power efficiency of 6.5 lm W −1 ). The devices without the HTL ( N, N ′-di-1-naphthyl- N, N ′-diphenylbenzidine (NPB)) exhibit performances comparable with or better than those of the devices with NPB. These results indicate that these compounds are promising luminescent materials for non-doped organic light-emitting diodes. Graphical abstract: Image 1 Highlights: AIEgens derived from rosin were synthesized by connecting TPE to DTPA via the C–C coupling reaction. The compounds exhibited good optical properties, AIE properties and thermal properties. Their HOMO and LUMO energy levels and electronic structure have been studied through experiments and theoretical calculations. The compounds are promising bifunctional materials for non-doped OLED applications.