Acceptor Derivatization of the 4CzIPN TADF System : Color Tuning and Introduction of Functional Groups

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Hundemer , F , von Reventlow , L G , Leonhardt , C , Polamo , M , Nieger , M , Seifermann , S M , Colsmann , A & Bräse , S 2019 , ' Acceptor Derivatization of the 4CzIPN TADF System : Color Tuning and Introduction of Functional Groups ' , Chemistryopen , vol. 8 , no. 12 , pp. 1413-1420 . https://doi.org/10.1002/open.201900141

Title: Acceptor Derivatization of the 4CzIPN TADF System : Color Tuning and Introduction of Functional Groups
Author: Hundemer, Fabian; von Reventlow, Lorenz Graf; Leonhardt, Celine; Polamo, Mika; Nieger, Martin; Seifermann, Stefan M.; Colsmann, Alexander; Bräse, Stefan
Contributor: University of Helsinki, Department of Chemistry
University of Helsinki, Department of Chemistry
Date: 2019-12
Language: eng
Number of pages: 8
Belongs to series: Chemistryopen
ISSN: 2191-1363
URI: http://hdl.handle.net/10138/309989
Abstract: We demonstrate modular modifications of the widely employed emitter 2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile (4CzIPN) by replacing one or both nitrile acceptors with oxadiazole groups via a tetrazole intermediate. This allows the introduction of various functional groups including halides, alkynes, alkenes, nitriles, esters, ethers and a protected amino acid while preserving the thermally activated delayed fluorescence (TADF) properties. The substituents control the emission maximum of the corresponding emitters, ranging between 472-527 nm, and show high solid-state photoluminescence quantum yields up to 85 %. The TADF emission of two compounds, 4CzCNOXDtBu and 4CzdOXDtBu, a mono- and a bis-oxadiazole substituted 4CzIPN is characterized in detail by time- and temperature-dependent photoluminescence. Solution-processed OLEDs comprising 4CzCNOXDtBu and 4CzdOXDtBu show a significant blue-shift of the emission compared to the reference 4CzIPN, with external quantum efficiencies of 16 %, 5.9 % and 17 % at 100 cd m(-2), respectively.
Subject: thermally activated delayed fluorescence
organic light emitting diodes (OLED)
oxadiazoles
color-tuning
functionalization
ACTIVATED DELAYED FLUORESCENCE
LIGHT-EMITTING-DIODES
BIPOLAR HOST
TRIPLET
MOLECULE
MECHANISMS
116 Chemical sciences
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