Perylene bisimides (PBIs) are among the best fluorophores but have to be enwrapped for optoelectronic applications by large and heavy substituents to prevent their ππ-stacking, which is known to accelerate non-radiative decay processes in the solid state. Here, light-weight di-tert-butylsilyl groups are introduced to bridge 1,12-dihydroxy and 1,6,7,12-tetrahydroxy PBIs to afford sublimable dyes for vacuum-processed optoelectronic devices. For both new compounds, this substitution provides a twisted and shielded perylene π-core whose, via OSiObridges, rigid structure affords well-resolved absorption and emission spectra with strong fluorescence in solution, as well as in the solid state. The usefulness of these dyes for vacuum-processed optoelectronic devices is demonstrated in organic light-emitting diodes (OLEDs) that show monomer-like emission spectra and high maximum external quantum efficiency (EQEmax) values of up to 3.1% for the doubly silicon-bridged PBI.
%0 Journal Article
%1 Brust_2022
%A Brust, Felix
%A Nagler, Oliver
%A Shoyama, Kazutaka
%A Stolte, Matthias
%A Würthner, Frank
%D 2022
%I Wiley
%J Adv. Optical Mater.
%K myown
%N 5
%R 10.1002/adom.202202676
%T Organic Light-Emitting Diodes Based on Silandiol-Bay-Bridged Perylene Bisimides
%U https://doi.org/10.1002%2Fadom.202202676
%V 11
%X Perylene bisimides (PBIs) are among the best fluorophores but have to be enwrapped for optoelectronic applications by large and heavy substituents to prevent their ππ-stacking, which is known to accelerate non-radiative decay processes in the solid state. Here, light-weight di-tert-butylsilyl groups are introduced to bridge 1,12-dihydroxy and 1,6,7,12-tetrahydroxy PBIs to afford sublimable dyes for vacuum-processed optoelectronic devices. For both new compounds, this substitution provides a twisted and shielded perylene π-core whose, via OSiObridges, rigid structure affords well-resolved absorption and emission spectra with strong fluorescence in solution, as well as in the solid state. The usefulness of these dyes for vacuum-processed optoelectronic devices is demonstrated in organic light-emitting diodes (OLEDs) that show monomer-like emission spectra and high maximum external quantum efficiency (EQEmax) values of up to 3.1% for the doubly silicon-bridged PBI.
@article{Brust_2022,
abstract = {Perylene bisimides (PBIs) are among the best fluorophores but have to be enwrapped for optoelectronic applications by large and heavy substituents to prevent their ππ-stacking, which is known to accelerate non-radiative decay processes in the solid state. Here, light-weight di-tert-butylsilyl groups are introduced to bridge 1,12-dihydroxy and 1,6,7,12-tetrahydroxy PBIs to afford sublimable dyes for vacuum-processed optoelectronic devices. For both new compounds, this substitution provides a twisted and shielded perylene π-core whose, via OSiObridges, rigid structure affords well-resolved absorption and emission spectra with strong fluorescence in solution, as well as in the solid state. The usefulness of these dyes for vacuum-processed optoelectronic devices is demonstrated in organic light-emitting diodes (OLEDs) that show monomer-like emission spectra and high maximum external quantum efficiency (EQEmax) values of up to 3.1% for the doubly silicon-bridged PBI.},
added-at = {2023-04-18T10:42:50.000+0200},
author = {Brust, Felix and Nagler, Oliver and Shoyama, Kazutaka and Stolte, Matthias and Würthner, Frank},
biburl = {https://www.bibsonomy.org/bibtex/2c9eb016a6fa227edf084ddcc8da6344f/wuerthner_group},
doi = {10.1002/adom.202202676},
interhash = {1ff716bce17e8794e37307e47eb6f0fc},
intrahash = {c9eb016a6fa227edf084ddcc8da6344f},
journal = {Adv. Optical Mater.},
keywords = {myown},
month = dec,
number = 5,
publisher = {Wiley},
timestamp = {2023-04-18T10:42:50.000+0200},
title = {Organic Light-Emitting Diodes Based on Silandiol-Bay-Bridged Perylene Bisimides},
url = {https://doi.org/10.1002%2Fadom.202202676},
volume = 11,
year = 2022
}