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DOI: 10.1055/s-0036-1590824
meta- and para-Functionalized Thermally Crosslinkable OLED-Materials through Selective Transition-Metal-Catalyzed Cross-Coupling Reactions
Publication History
Received: 03 April 2017
Accepted after revision: 06 June 2017
Publication Date:
26 July 2017 (online)
Abstract
Herein, a synthetic approach using selective transition-metal-catalyzed cross-coupling reactions to thermally crosslinkable OLED materials based on vinyl-functionalized arylamines is reported. In a modular approach, 9,9-dialkyl-2,7-diiodo-9H-fluorene underwent a selective Ullmann cross-coupling reaction with bromo-substituted-diphenylamines to give 9,9-dialkyl-2,7-bis(bromo-substituted-diphenylamino)-9H-fluorenes that underwent end-functionalization by the Suzuki–Miyaura reaction using potassium vinyltrifluoroborate to give the corresponding 9,9-dialkyl-2,7-bis(vinyl-substituted-diphenylamino)-9H-fluorenes. Novel meta-functionalized materials were synthesized, which are difficult to prepare by traditional synthetic pathways. The thermal behavior of the compounds was investigated by DSC measurements, indicating a lower thermal sensitivity of the meta-substituted materials than their para-functionalized analogues.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590824.
- Supporting Information
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