Soluble flavanthrone derivatives: synthesis, characterization, and application to organic light-emitting diodes

Kamil Kotwica , Piotr Bujak , Przemysław Data , Wojciech Krzywiec , Damian Wamil , Piotr Guńka , Łukasz Skórka , Tomasz Jaroch , Robert Nowakowski , Adam Proń , Andrew Monkman

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 sub-sequent 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 P1 and forms pi-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%. Copyright John Wiley Publishing
Author Kamil Kotwica KChTP
Kamil Kotwica,,
- Chair Of Polymer Chemistry And Technology
, Piotr Bujak KChTP
Piotr Bujak,,
- Chair Of Polymer Chemistry And Technology
, Przemysław Data - [University of Durham (UK)]
Przemysław Data,,
-
- University of Durham
, Wojciech Krzywiec KChTP
Wojciech Krzywiec,,
- Chair Of Polymer Chemistry And Technology
, Damian Wamil KChTP
Damian Wamil,,
- Chair Of Polymer Chemistry And Technology
, Piotr Guńka KChNTCS
Piotr Guńka,,
- Chair Of Inorganic Chemistry And Solid State Technology
, Łukasz Skórka KChTP
Łukasz Skórka,,
- Chair Of Polymer Chemistry And Technology
, Tomasz Jaroch - [Institute of Physical Chemistry Polish Academy of Sciences (IChF PAN)]
Tomasz Jaroch,,
-
- Instytut Chemii Fizycznej Polskiej Akademii Nauk
, Robert Nowakowski - [Institute of Physical Chemistry Polish Academy of Sciences (IChF PAN)]
Robert Nowakowski,,
-
- Instytut Chemii Fizycznej Polskiej Akademii Nauk
, Adam Proń KChTP
Adam Proń,,
- Chair Of Polymer Chemistry And Technology
et al.`
Journal seriesChemistry-A European Journal, ISSN 0947-6539
Issue year2016
Vol22
No23
Pages7978-7986
Publication size in sheets0.5
Keywords in Englishsoluble flavanthrone derivatives, synthesis, characterization, application, organic light-emitting diodes
DOIDOI:10.1002/chem.201600513
URL http://onlinelibrary.wiley.com/doi/10.1002/chem.201600513/abstract
Languageen angielski
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Kotwica_et_al-2016-Chemistry_-_A_European_Journal.pdf 1.29 MB
Score (nominal)40
ScoreMinisterial score = 40.0, 28-11-2017, ArticleFromJournal
Ministerial score (2013-2016) = 40.0, 28-11-2017, ArticleFromJournal
Publication indicators WoS Impact Factor: 2016 = 5.317 (2) - 2016=5.184 (5)
Citation count*4 (2018-07-17)
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* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.
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