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Issue 8, 2016
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Thioxanthene and dioxothioxanthene dihydroindeno[2,1-b]fluorenes: synthesis, properties and applications in green and sky blue phosphorescent OLEDs

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Abstract

We report herein the synthesis, and structural, electrochemical and photophysical 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 derivative 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 organic electronics.

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

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Publication details

The article was received on 30 Nov 2015, accepted on 23 Jan 2016 and first published on 25 Jan 2016


Article type: Paper
DOI: 10.1039/C5TC04039F
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Citation: J. Mater. Chem. C, 2016,4, 1692-1703

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

    M. Romain, C. Quinton, D. Tondelier, B. Geffroy, O. Jeannin, J. Rault-Berthelot and C. Poriel, J. Mater. Chem. C, 2016, 4, 1692
    DOI: 10.1039/C5TC04039F

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