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Journal of Luminescence

Volume 129, Issue 10, October 2009, Pages 1207-1214

Synthesis and electroluminescence properties of


benzothiazole derivatives
Hui-ying Fua, Xin-dong Gaob, Gao-yu Zhonga, Zhi-yang Zhonga, Fei Xiaoa, , and Bing-xian Shaoa
a
Department of Materials Science, Fudan University, Shanghai 200433, China
b
State Key Laboratory of Applied Surface Physics, Fudan University, Shanghai 200433, China
Received 29 May 2008;
revised 18 February 2009;
accepted 3 June 2009.
Available online 8 June 2009.

Abstract
Benzothiazole-based blue fluorescent materials N-(4-(benzo[d]thiazol-2-yl)phenyl)-N-phenylbenzenamine
(BPPA) and N-(4-(benzo[d]thiazol-2-yl)phenyl)-N-phenylnaphthalen-1-amine (BPNA) were synthesized for
use in organic light-emitting diodes (OLEDs). Electroluminescent device with a configuration of
ITO/NPB/BPPA/BCP/Alq3/LiF/Al showed a maximum brightness of 3760 cd/m2 at 14.4 V with the CIE
coordinates of (0.16, 0.16). A current efficiency of 3.01 cd/A and an external quantum efficiency of 2.37% at
20 mA/cm2 were obtained from this device. Molecules derived from BPPA and BPNA with incorporated
dicyanomethylidene, which is a functional group for most red fluorescent molecules, were designed,
synthesized and characterized to study the red fluorescence properties of the benzothiazole derivatives.

Keywords: Benzothiazole; Organic light-emitting diodes; Electroluminescence

PACS classification codes: 78.60.Fi; 78.55.Kz

Article Outline

1.
Introduction

2.
Experimental section
2.1. General information
2.2. Materials
2.3. N-(4-(benzo[d]thiazol-2-yl)phenyl)-N-phenylaniline (BPPA)
2.4. N-(4-(benzo[d]thiazol-2-yl)phenyl)-N-phenyl-1-naphthylamine (BPNA)
2.5. N-(4-benzo[d]thiazol-2-ylphenyl)-N-(4-formylphenyl)aniline (BPPAF)
2.6. N-(4-benzo[d]thiazol-2-ylphenyl)-N-(4-formylphenyl)-1-naphthylamine (BPNAF)
2.7. N-(4-(benzo[d]thiazol-2-yl)phenyl)N-(4-(2-(3-dicyanomethylidene-5,5-dimethylcyclohexenyl)
vinyl)phenyl)aniline (BPPA-2CN)
2.8. N-(4-(benzo[d]thiazol-2-yl)phenyl)N-(4-(2-(3-dicyanomethylidene-5,5-dimethylcyclohexenyl)
vinyl)phenyl)-1-naphthylamine (BPNA-2CN)
2.9. Fabrication and characterization of OLEDs

3.
Results and discussion
3.1. Synthesis and characterization
3.2. Optical and electrochemical properties
3.3. Blue OLEDs based on BPPA and BPNA
3.4. Red OLEDs based on BPPA-2CN and BPNA-2CN

4.
Conclusion
Acknowledgements
References

Scheme 1. Molecular structures of BPPA, BPNA, BPPA-2CN and BPNA-2CN.

Scheme 2. Synthetic route of the benzothiazole derivatives.

Fig. 1. STM topographies: (A) BPNA; (B) BPPA-2CN; (C) BPPA-2CN;


and (D) BPNA-2CN.

Fig. 2. Normalized absorption and PL spectra of the benzothiazole


derivatives.

Fig. 3. Cyclic voltammogram of BPPA and BPNA, collected at a scan


rate=200 mV/s.

Fig. 4. EL spectra of the BPPA-based devices.


Fig. 5. PL spectrum of the BPNA film and EL spectrum of the BPNA-
based device.

Fig. 6. Luminance–voltage and current density–voltage diagrams of


Device 1–3.

Fig. 7. Current efficiency–current density characteristics of Device 1–3.

Fig. 8. PL and EL spectra of the red emitters: (A) BPPA-2CN and (B)
BPNA-2CN.

Fig. 9. Luminance–voltage diagrams of BPPA-2CN based devices.

Table 1.

Physical data for the compounds.

a
Obtained from cyclic voltammetric methods. ELUMO (or
EHOMO)=4.75+e·Vreduction (or Voxidation).
b
Electrochemical band gap: EHOMO−ELUMO.
c
Optical bandwidth, obtained from the optical absorption edge.
d
na: not observed.
Table 2.

Device structures and performance of OLEDs based on BPPA and


BPNA.

a
Turn-on voltage.
b
Measured at 20 mA/cm2.

Corresponding author. Tel.: +86 21 6564 2110; fax: +86 21 651 03056.
Geometric and Excited-State Properties of 1,4-
Bis(benzothiazolylvinyl)benzene Interacting with 2,2‘,2‘ ‘-(1,3,5-
phenylene)tris[1-phenyl-1H-benzimidazole] Studied by a Density-
Functional Tight-Binding Method
• Abstract
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• Figures
• Citing Articles
C. S. Lin, R. Q. Zhang,* and C. S. Lee
Center of Super-Diamond and Advanced Films (COSDAF) and Department of Physics and Materials
Science, City University of Hong Kong, Hong Kong SAR, China
T. A. Niehaus and Th. Frauenheim
Bremen Center for Computational Material Science, University Bremen, 28334 Bremen, Germany
J. Phys. Chem. B, 2006, 110 (42), pp 20847–20851
DOI: 10.1021/jp061864v
Publication Date (Web): September 27, 2006
Copyright © 2006 American Chemical Society

Sonogashira Coupling on an Extended Gold Surface in Vacuo: Reaction of


Phenylacetylene with Iodobenzene on Au(111)
• Abstract
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• Supporting Info
• Figures
• Citing Articles
Vijay K. Kanuru, Georgios Kyriakou, Simon K. Beaumont, Anthoula C.
Papageorgiou, David J. Watson† and Richard M. Lambert*
Department of Chemistry, University of Cambridge, Cambridge CB2 1EW, United
Kingdom
J. Am. Chem. Soc., 2010, 132 (23), pp 8081–8086
DOI: 10.1021/ja1011542
Publication Date (Web): May 21, 2010
Copyright © 2010 American Chemical Society
rml1@cam.ac.uk, †
Present address: Department of Chemistry, University of Reading, Whiteknights,
Reading RG6 6AD, United Kingdom.
Abstract

Temperature-programmed reaction measurements supported by scanning tunneling


microscopy have shown that phenylacetylene and iodobenzene react on smooth Au(111)
under vacuum conditions to yield biphenyl and diphenyldiacetylene, the result of
homocoupling of the reactant molecules. They also produce diphenylacetylene, the result
of Sonogashira cross-coupling, prototypical of a class of reactions that are of paramount
importance in synthetic organic chemistry and whose mechanism remains controversial.
Roughened Au(111) is completely inert toward all three reactions, indicating that the
availability of crystallographically well-defined adsorption sites is crucially important.
High-resolution X-ray photoelectron spectroscopy and near-edge X-ray absorption fine
structure spectroscopy show that the reactants are initially present as intact, essentially
flat-lying molecules and that the temperature threshold for Sonogashira coupling
coincides with that for C−I bond scission in the iodobenzene reactant. The fractional-
order kinetics and low temperature associated with desorption of the Sonogashira product
suggest that the reaction occurs at the boundaries of islands of adsorbed reactants and that
its appearance in the gas phase is rate-limited by the surface reaction. These findings
demonstrate unambiguously and for the first time that this heterogeneous cross-coupling
chemistry is an intrinsic property of extended, metallic pure gold surfaces: no other
species, including solvent molecules, basic or charged (ionic) species are necessary to
mediate the process

Tetrahedron Letters
Volume 16, Issue 50, 1975, Pages 4467-4470

doi:10.1016/S0040-4039(00)91094-3 | How to Cite or Link Using DOI


Copyright © 1975 Published by Elsevier Science Ltd. All rights reserved. Permissions
& Reprints
A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen
with bromoalkenes, iodoarenes and bromopyridines
Kenkichi Sonogashira, Yasuo Tohda and Nobue Hagihara
Scientific and Industrial Research, Osaka University, Yamadakami, Suita, Osaka 565,
Japan
Received 4 October 1975.
Available online 11 May 2001.

The Sonogashira Reaction: A Booming Methodology in Synthetic Organic


Chemistry†
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Rafael Chinchilla* and Carmen Nájera*
Departamento de Química Orgánica and Instituto de Síntesis Orgánica (ISO),
Universidad de Alicante, Facultad de Ciencias, Apartado 99, 03080 Alicante, Spain
Chem. Rev., 2007, 107 (3), pp 874–922
DOI: 10.1021/cr050992x
Publication Date (Web): February 17, 2007
Copyright © 2007 American Chemical Society

Table of Contents
• 1. Introduction
• 2. Mechanistic Considerations
• 3. Catalysts and Reaction Conditions
o 3.1. Palladium−Phosphorus Complexes3.1.1. Unsupported
Palladium−Phosphorus Complexes
• 3.1.2. Supported Palladium−Phosphorus Complexes

o 3.2. Palladium−Nitrogen Complexes3.2.1. Unsupported
Palladium−Nitrogen Complexes
• 3.2.2. Supported Palladium−Nitrogen Complexes

o 3.3. Palladium−P,N- and Palladium−P,O Complexes

o 3.4. N-Heterocyclic Carbene (NHC) Palladium Complexes3.4.1.
Unsupported NHC Palladium Complexes
• 3.4.2. Supported NHC Palladium Complexes

o 3.5. Palladacycle Catalysts3.5.1. Unsupported Palladacycles
• 3.5.2. Supported Palladacycles

o 3.6. Ligand-Free Palladium Catalysts3.6.1. Unsupported Ligand-Free
Palladium Catalysts
• 3.6.2. Solid-Supported Ligand-Free Palladium Catalysts

o 3.7. Palladium Nanoparticles as Catalysts

o 3.8. Other Transition-Metal Complexes

o 3.9. Transition-Metal-Free Reactions
• 4. Applications
o 4.1. Alkynylation of Arenes

o 4.2. Alkynylation of Heterocycles

o 4.3. Synthesis of Enynes and Enediynes

o 4.4. Synthesis of Ynones

o 4.5. Synthesis of Carbocyclic Systems

o 4.6. Synthesis of Heterocyclic Systems

o 4.7. Synthesis of Natural Products

o 4.8. Synthesis of Electronic and Electrooptical Molecules

o 4.9. Synthesis of Molecules for Nanostructures
• 5. Conclusions
• 6. Acknowledgments

• Solar Energy
Volume 80, Issue 2, February 2006, Pages 209-214
Solar Cells and Solar Energy Materials 2004

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