Journal
DYES AND PIGMENTS
Volume 121, Issue -, Pages 138-146Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2015.05.002
Keywords
Synthesis; Photophysical property; Organic light-emitting diodes; Pyrazolo[3,4-b]quinoline; Stokes shift; Structure-property relationship
Funding
- National Natural Science Foundation of China [21302122, 21072127, 21032006, 21172141, 21302121]
- Science and Technology Commission of Shanghai Municipality [13ZR1416600]
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Organic dyes containing trifluoromethylated-pyrazolo[3, 4-b]quinoline were synthesized by using condensation reaction between substituted pyrazolo-4-formaldehyde and aryl amines in moderate yields. Quantum calculation, electrochemical, photophysical, and electroluminescent properties were discussed in detail. Electron-withdrawing groups at 6-position of dyes stabilized the LUMO energy levels significantly resulting in red-shifted absorption/emission spectra. Addition of electron-donating group destabilized the HOMO strongly and the LUMO energy levels slightly resulting in red-shifted absorption maxima, but in blue-shifted emission maxima. Experimental and quantum calculation results are presented here to explain this unusual phenomenon. A linear relationship of dipole moments versus Stokes shifts is obtained for these fluorophores, where the increase of dipole moment is accompanied by a decrease in Stokes shift. Organic light-emitting diodes based on selected dyes showed emission at 456 nm, maximum external quantum efficiency at 1.43%, and current efficiency at 1.95 cd/A. (C) 2015 Elsevier Ltd. All rights reserved.
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