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. 2021 Dec 15;26(24):7596.
doi: 10.3390/molecules26247596.

New Unsymmetrically Substituted Benzothiadiazole-Based Luminophores: Synthesis, Optical, Electrochemical Studies, Charge Transport, and Electroluminescent Characteristics

Pavel S Gribanov  1 , Dmitry A Loginov  1 , Dmitry A Lypenko  2 , Artem V Dmitriev  2 , Sergey I Pozin  2 , Alexey E Aleksandrov  2 , Alexey R Tameev  2 , Igor L Martynov  3 , Andrey Yu Chernyadyev  2 , Sergey N Osipov  1
Affiliations

New Unsymmetrically Substituted Benzothiadiazole-Based Luminophores: Synthesis, Optical, Electrochemical Studies, Charge Transport, and Electroluminescent Characteristics

Pavel S Gribanov et al. Molecules. .

Abstract

Three new benzothiadiazole (BTD)-containing luminophores with different configurations of aryl linkers have been prepared via Pd-catalyzed cross-coupling Suzuki and Buchwald-Hartwig reactions. Photophysical and electroluminescent properties of the compounds were investigated to estimate their potential for optoelectronic applications. All synthesized structures have sufficiently high quantum yields in film. The BTD with aryl bridged carbazole unit demonstrated the highest electrons and holes mobility in a series. OLED with light-emitting layer (EML) based on this compound exhibited the highest brightness, as well as current and luminous efficiency. The synthesized compounds are not only luminophores with a high photoluminescence quantum yield, but also active transport centers for charge carriers in EML of OLED devices.

Keywords: OLED; benzothiadiazole; cross-coupling; luminescence; luminophore; phosphorescence.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structures of the BTD Dyes D1, D2, D3.
Scheme 1
Scheme 1
Synthesis of dyes D1, D2, D3.
Figure 2
Figure 2
Optical spectra of D1, D2, D3 in m-xylene (concentration 10−5 M, optical length 1 cm, λex = 375–400 nm). (I) Absorption and photoluminescence at room temperature; (II) photoluminescence and phosphorescence (delay 1 ms) at 77 K.
Figure 2
Figure 2
Optical spectra of D1, D2, D3 in m-xylene (concentration 10−5 M, optical length 1 cm, λex = 375–400 nm). (I) Absorption and photoluminescence at room temperature; (II) photoluminescence and phosphorescence (delay 1 ms) at 77 K.
Figure 3
Figure 3
Photoluminescence decay curves of D1, D2, D3 in semilogarithmic scale. λex = 355 nm, λem = 550 nm.
Figure 4
Figure 4
(a) OLED based on EML with the D3 (10 wt %)/mCP composite; (b) the CIE chromaticity diagram recorded at 8 V.
Figure 5
Figure 5
EL spectra of the studied OLEDs.
Figure 6
Figure 6
Energy band diagram of OLED structure ITO/TAPC (60 nm)/D3 (10 wt %): mCP (25 nm)/TPYMB(30 nm)/LiF (1 nm)/Al.
Figure 7
Figure 7
(a) Voltage-current density and (b) voltage-brightness characteristics of the OLEDs based on EML with the D1–3/mCP composites.
See this image and copyright information in PMC

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