Organic Light-Emitting Diodes Based on Silandiol-Bay-Bridged Perylene Bisimides

被引:12
作者
Brust, Felix [1 ]
Nagler, Oliver [1 ]
Shoyama, Kazutaka [1 ,2 ]
Stolte, Matthias [1 ,2 ]
Wuerthner, Frank [1 ,2 ]
机构
[1] Univ Wurzburg, Ctr Nanosyst Chem CNC, Theodor Boveri Weg, D-97074 Wurzburg, Germany
[2] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
关键词
organic light emitting diodes; perylene bisimide dyes; rigidification; solid-state emission; vacuum processable; SOLID-STATE FLUORESCENCE; SOLAR CONCENTRATORS; DYE; PERFORMANCE; EMITTERS; LASERS; RED;
D O I
10.1002/adom.202202676
中图分类号
T [工业技术];
学科分类号
08 ;
摘要
Perylene bisimides (PBIs) are among the best fluorophores but have to be enwrapped for optoelectronic applications by large and heavy substituents to prevent their pi-pi-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 pi-core whose, via O-Si-O-bridges, 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 (EQE(max)) values of up to 3.1% for the doubly silicon-bridged PBI.
引用
收藏
页数:8
相关论文
共 52 条
[31]  
REISFELD R, 1990, CHIMIA, V44, P295
[32]   Substituent-dependent absorption and fluorescence properties of perylene bisimide radical anions and dianions [J].
Renner, Rebecca ;
Stolte, Matthias ;
Heitmueller, Julia ;
Brixner, Tobias ;
Lambert, Christoph ;
Wuerthner, Frank .
MATERIALS HORIZONS, 2022, 9 (01) :350-359
[33]   Molecularly isolated perylene diimides enable both strong exciton-photon coupling and high photoluminescence quantum yield [J].
Sabatini, Randy P. ;
Zhang, Bolong ;
Gupta, Akhil ;
Leoni, Julien ;
Wong, Wallace W. H. ;
Lakhwani, Girish .
JOURNAL OF MATERIALS CHEMISTRY C, 2019, 7 (10) :2954-2960
[34]  
Schmidt D., 2019, ANGEW CHEM, V131, P13519
[35]   Protein-like Enwrapped Perylene Bisimide Chromophore as a Bright Microcrystalline Emitter Material [J].
Schmidt, David ;
Stolte, Matthias ;
Suess, Jasmin ;
Liess, Andreas ;
Stepanenko, Vladimir ;
Wuerthner, Frank .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (38) :13385-13389
[36]   Reactions of complex ligands, part 101.: Novel [6]- and [7]helicene-like quinones via mono- and bidirectional chromium-templated benzannulation of bridged binaphthyl carbene complexes [J].
Schneider, JF ;
Nieger, M ;
Nättinen, K ;
Lewall, B ;
Niecke, E ;
Dötz, KH .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (08) :1541-1560
[37]   NEW PERYLENE AND VIOLANTHRONE DYESTUFFS FOR FLUORESCENT COLLECTORS [J].
SEYBOLD, G ;
WAGENBLAST, G .
DYES AND PIGMENTS, 1989, 11 (04) :303-317
[38]  
Sol J. A., 2018, ANGEW CHEM, V130, P1042
[39]   Temperature-Responsive Luminescent Solar Concentrators: Tuning Energy Transfer in a Liquid Crystalline Matrix [J].
Sol, Jeroen A. H. P. ;
Dehm, Volker ;
Hecht, Reinhard ;
Wuerthner, Frank ;
Schenning, Albertus P. H. J. ;
Debije, Michael G. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (04) :1030-1033
[40]   Spectroscopic Demonstration of Exciton Dynamics and Excimer Formation in a Sterically Controlled Perylene Bisimide Dimer Aggregate [J].
Son, Minjung ;
Park, Kyu Hyung ;
Shao, Changzhun ;
Wuerthner, Frank ;
Kim, Dongho .
JOURNAL OF PHYSICAL CHEMISTRY LETTERS, 2014, 5 (20) :3601-3607