Soluble Flavanthrone Derivatives: Synthesis, Characterization, and Application to Organic Light-Emitting Diodes

Kotwica, Kamil; Bujak, Piotr; Data, Przemyslaw; Krzywiec, Wojciech; Wamil, Damian; Gunka, Piotr A.; Skorka, Lukasz; Jaroch, Tomasz; Nowakowski, Robert; Pron, Adam; Monkman, Andrew

Abstract

Simple modification of benzo[h]benz[5,6]acridino[2,1,9,8-klmna]acridine-8,16-dione, an old and almost-forgotten vat dye, by reduction of its carbonyl groups and subsequent O-alkylation, yields solution-processable, electroactive, conjugated compounds of the periazaacene type, suitable for the use in organic electronics. Their electrochemically determined ionization potential and electron affinity of about 5.2 and −3.2 eV, respectively, are essentially independent of the length of the alkoxyl substituent and in good agreement with DFT calculations. The crystal structure of 8,16-dioctyloxybenzo[h]benz[5,6]acridino[2,1,9,8-klmna]acridine (FC-8), the most promising compound, was solved. It crystallizes in space group Pmath formula and forms π-stacked columns held together in the 3D structure by dispersion forces, mainly between interdigitated alkyl chains. Molecules of FC-8 have a strong tendency to self-organize in monolayers deposited on a highly oriented pyrolytic graphite surface, as observed by STM. 8,16-Dialkoxybenzo[h]benz[5,6]acridino[2,1,9,8-klmna]acridines are highly luminescent, and all have photoluminescence quantum yields of about 80 %. They show efficient electroluminescence, and can be used as guest molecules with a 4,4′-bis(N-carbazolyl)-1,1′-biphenyl host in guest/host-type organic light-emitting diodes. The best fabricated diodes showed a luminance of about 1900 cd m−12, a luminance efficiency of about 3 cd A−1, and external quantum efficiencies exceeding 0.9 %.

Citation

Kotwica, K., Bujak, P., Data, P., Krzywiec, W., Wamil, D., Gunka, P. A., …Monkman, A. (2016). Soluble Flavanthrone Derivatives: Synthesis, Characterization, and Application to Organic Light-Emitting Diodes. Chemistry - A European Journal, 22(23), 7978-7986. https://doi.org/10.1002/chem.201600513

• Journal Article Type: Article
• Acceptance Date: Feb 3, 2016
• Online Publication Date: Apr 23, 2016
• Publication Date: Jun 1, 2016
• Deposit Date: Aug 8, 2017
• Publicly Available Date: Jan 3, 2024
• Journal: Chemistry - A European Journal
• Print ISSN: 0947-6539
• Electronic ISSN: 1521-3765
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 22
• Issue: 23
• Pages: 7978-7986
• DOI: https://doi.org/10.1002/chem.201600513
• Public URL: https://durham-repository.worktribe.com/output/1379607