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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| Main Authors: | , , , , , , , , , , |
|---|---|
| Format: | Article (Journal) |
| Language: | English |
| Published: |
June 4, 2018
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| In: |
Chemistry of materials
Year: 2018, Volume: 30, Issue: 12, Pages: 4157-4167 |
| ISSN: | 1520-5002 |
| DOI: | 10.1021/acs.chemmater.8b01703 |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/acs.chemmater.8b01703
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| Author Notes: | 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 |
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| 520 | |a 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. | ||
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