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Solubility modulation of polyfluorene emitters by thermally induced (retro)-Diels-Alder cross-linking of cyclopentadienyl substituents

For cost-efficient organic electronic devices, the consecutive deposition of active layers by solution-based processes is a key benefit. We report a synthetic approach enabling solubility reduction of bis(cyclopentadienyl)-substituted polyfluorenes as emissive layers in organic light-emitting diodes...

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Hauptverfasser: Ahrens, Lukas (VerfasserIn) , Schlißke, Stefan (VerfasserIn) , Strunk, Karl-Philipp (VerfasserIn) , Hinkel, Felix Peter (VerfasserIn) , Melzer, Christian (VerfasserIn) , Bunz, Uwe H. F. (VerfasserIn) , Lemmer, Uli (VerfasserIn) , Hernandez-Sosa, Gerardo (VerfasserIn) , Jänsch, Daniel (VerfasserIn) , Freudenberg, Jan (VerfasserIn) , Müllen, Klaus (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: June 4, 2018
In: Chemistry of materials
Year: 2018, Jahrgang: 30, Heft: 12, Pages: 4157-4167
ISSN:1520-5002
DOI:10.1021/acs.chemmater.8b01703
Online-Zugang:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/acs.chemmater.8b01703
Volltext
Verfasserangaben:Lukas Ahrens, Stefan Schlisske, Karl-Philipp Strunk, Felix Hinkel, Christian Melzer, Uwe H.F. Bunz, Uli Lemmer, Gerardo Hernandez-Sosa, Daniel Jänsch, Jan Freudenberg, and Klaus Müllen
Beschreibung
Zusammenfassung:For cost-efficient organic electronic devices, the consecutive deposition of active layers by solution-based processes is a key benefit. We report a synthetic approach enabling solubility reduction of bis(cyclopentadienyl)-substituted polyfluorenes as emissive layers in organic light-emitting diodes (OLEDs). Thermally induced retro-Diels-Alder reaction liberates free cyclopentadiene as “protecting group” and pending cyclopentadienyl units, which cross-link the polymer strands upon cooling via [4+2] cycloadditions. The activation temperature is tuned in the range of 180-250 °C through alkyl, alkoxy, or ester linkages. Ultimately, macrocyclic self-protected bis(cyclopentadienylene) moieties avoid extrusion of volatile cyclopentadiene during activation. The solvent resistance of the emissive layers after cross-linking is examined by absorption spectroscopy and white light scanning interferometry. The influence of the desolubilization procedure on the performance of solution-processed OLEDs is investigated.
Beschreibung:Gesehen am 28.04.2020
Beschreibung:Online Resource
ISSN:1520-5002
DOI:10.1021/acs.chemmater.8b01703

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