Title Effect of substituents with the different electron-donating abilities on optoelectronic properties of bipolar thioxanthone derivatives /
Authors Macionis, Simas ; Gudeika, Dalius ; Volyniuk, Dmytro ; Mahmoudi, Malek ; Simokaitiene, Jurate ; Andruleviciene, Viktorija ; Najafov, Murad ; Sadzeviciene, Rita ; Stoncius, Sigitas ; Grazulevicius, Juozas V
DOI 10.1021/acsaelm.3c00092
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Is Part of ACS applied electronic materials.. Washington, DC : American chemical society. 2023, vol. 5, iss. 4, p. 2227-2238.. ISSN 2637-6113
Keywords [eng] acridane ; carbazole ; electroluminescence ; organic light-emitting diode ; phenothiazine ; solid-state luminescence enhancement ; thermally activated delayed fluorescence ; thioxanthone
Abstract [eng] The synthesis and optoelectronic properties of four simple-structure thioxanthone derivatives employing thioxanthone as an acceptor unit, coupled with moieties having very different electron-donating abilities such as phenoxazine, 3,6-di-tert-butylcarbazole, 3,7-di-tert-butylphenothiazine, or 2,7-di-tert-butyl-9,9-dimethylacridane, are reported. The compounds form molecular glasses with glass transition temperatures reaching 116 °C. Ionization potentials of the compounds estimated by photoelectron emission method range from 5.42 to 5.74 eV. Thioxanthone derivatives containing 3,6-tert-butylcarbazole or 2,7-di-tert-butyl-9,9-dimethylacridane moieties with weak electron-donating strengths were characterized by bipolar charge transport with relatively close hole and electron mobility values of 6.8 × 10-5/2.4 × 10-5 and 3.1 × 10-5/4.6 × 10-6 cm2/(V s) recorded at 3.6 × 105 V/cm. The other compounds demonstrated hole-transporting properties. The films of thioxanthones containing phenoxazine or 2,7-di-tert-butyl-9,9-dimethylacridane moieties showed efficient thermally activated delayed fluorescence with a photoluminescence quantum yield of up to 50% due to the solid-state luminescence enhancement. Organic-light-emitting diodes containing the synthesized compounds as emitters showed very different external quantum efficiencies (0.9-10.3%) and blue, sky blue, green, or yellow electroluminescence colors, thus reflecting the effects of donor substituents.
Published Washington, DC : American chemical society
Type Journal article
Language English
Publication date 2023
CC license CC license description