High triplet energy host material with a 1,3,5-oxadiazine core from a one-step interrupted Fischer indolization

IF 5.9 2区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY
Charlotte Riley, Hwan-Hee Cho, Alexander C. Brannan, Nguyen Le Phuoc, Mikko Linnolahti, Neil C. Greenham, Alexander S. Romanov
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Abstract

Energy-efficient and deep-blue organic light-emitting diode (OLED) with long operating stability remains a key challenge to enable a disruptive change in OLED display and lighting technology. Part of the challenge is associated with a very narrow choice of the robust host materials having over 3 eV triplet energy level to facilitate efficient deep-blue emission and deliver excellent performance in the OLED device. Here we show the molecular design of new 1,3,5-oxadiazines (NON)-host materials with high triplet energy over 3.2 eV, enabling deep-blue OLED devices with a peak external quantum efficiency of 21%. A series of NON-host materials are prepared by the condensation of substituted arylhydrazines and cyclohexylcarbaldehyde in a 2:3 ratio. This straightforward “one-pot” procedure enables the formation of indoline-containing derivatives with three fused heterocyclic rings and two stereogenic centres. All materials emit UV-fluorescence in the range of 315–338 nm while possessing highly desirable characteristics for application in deep-blue OLED devices: good thermal stability, a wide energy gap (3.9 eV), a high triplet energy level of (3.3 eV), and excellent volatility during sublimation. Diluting phosphorescent and thermally activated delayed fluorescence emitter molecules in solid-state host matrices has proven to be a useful strategy to hinder self-quenching mechanisms, but host materials must meet several criteria to enable energy efficient and stable OLEDs. Here, the authors report the synthesis of a series of 1,3,5-oxadiazines from a one-pot interrupted Fischer indolization, and demonstrate that they possess highly desirable characteristics as host materials in deep-blue OLED devices.

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来源期刊
Communications Chemistry
Communications Chemistry Chemistry-General Chemistry
CiteScore
7.70
自引率
1.70%
发文量
146
审稿时长
13 weeks
期刊介绍: Communications Chemistry is an open access journal from Nature Research publishing high-quality research, reviews and commentary in all areas of the chemical sciences. Research papers published by the journal represent significant advances bringing new chemical insight to a specialized area of research. We also aim to provide a community forum for issues of importance to all chemists, regardless of sub-discipline.
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