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

Hundemer, Fabian; Reventlow, Lorenz Graf von; Leonhardt, Céline; Polamo, Mika; Nieger, Martin; Seifermann, Stefan M.; Colsmann, Alexander; Bräse, Stefan

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 temperaturedependent 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 cdm⁻², respectively.

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Verlagsausgabe §
DOI: 10.5445/IR/1000105978
Veröffentlicht am 20.02.2020
Originalveröffentlichung
DOI: 10.1002/open.201900141
Scopus
Zitationen: 1
Web of Science
Zitationen: 1
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Lichttechnisches Institut (LTI)
Materialwissenschaftliches Zentrum für Energiesysteme (MZE)
Institut für Toxikologie und Genetik (ITG)
Publikationstyp Zeitschriftenaufsatz
Publikationsmonat/-jahr 12.2019
Sprache Englisch
Identifikator ISSN: 2191-1363, 2191-1363
KITopen-ID: 1000105978
HGF-Programm 47.01.01 (POF III, LK 01)
Biol.Netzwerke u.Synth.Regulat. ITG+ITC
Erschienen in ChemistryOpen
Band 8
Heft 12
Seiten 1413–1420
Vorab online veröffentlicht am 13.12.2019
Nachgewiesen in Scopus
Web of Science
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