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Thioxanthene and dioxothioxanthene dihydroindeno[2,1-b]fluorenes: synthesis, properties and applications in green and sky blue phosphorescent OLEDs

Abstract : We report herein the synthesis, and structural, electrochem. and photophys. properties of new dihydroindeno[2,1-b]fluorene-based semi-conductors, i.e. dispiro[thioxanthene-9,5'-indeno[2,1-b]fluorene-7',9''-thioxanthene] 2 and dispiro-[dioxothioxanthene-9,5'-indeno[2,1-b]fluorene-7',9''-thioxanthene] 3. These properties will be compared to those of the pure hydrocarbon deriv. dispiro[fluorene-9,5'-indeno[2,1-b]fluorene-7',9''-fluorene] 1 previously described. The incorporation of the sulfur atom within the bridged units allows tuning the HOMO and LUMO energy levels, nevertheless retaining the high ET of the dihydroindeno[2,1-b]fluorenyl core ([2,1-b]IF), the key feature of further device applications. This control of the properties has allowed incorporating 3 as the host material in blue and green phosphorescent OLEDs (PhOLEDs) with an EQE of 12.8% (at 1 mA cm-2 with the corresponding CE and PE of 48.6 cd A-1 and 29.5 lm W-1) for the green device and an EQE of 4.8% (at 1 mA cm-2 with the corresponding CE and PE of 14.8 cd A-1 and 8.2 lm W-1) for the sky-blue device. To the best of our knowledge, this work is the second example of incorporation of a dihydroindeno[2,1-b]fluorene based semi-conductor in a blue PhOLED and highlights the potential of this fragment in org. electronics.
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01274109
Contributor : Laurent Jonchère <>
Submitted on : Monday, February 15, 2016 - 2:07:12 PM
Last modification on : Thursday, July 30, 2020 - 3:07:40 AM

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Maxime Romain, Cassandre Quinton, Denis Tondelier, Bernard Geffroy, Olivier Jeannin, et al.. Thioxanthene and dioxothioxanthene dihydroindeno[2,1-b]fluorenes: synthesis, properties and applications in green and sky blue phosphorescent OLEDs. Journal of Materials Chemistry C, Royal Society of Chemistry, 2016, 4 (8), pp.1692-1703. ⟨10.1039/C5TC04039F⟩. ⟨hal-01274109⟩

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