Organic Letters
Letter
Table 2. Electroluminescent (EL) Device Performance
CIE
voltage (V) luminescence, L (cd/m2) luminous efficiency, ηc (cd/A) power efficiency, ηp (lm/W) external quantum efficiency, EQE (%)
x
y
2.8
4.0
7.0
8.0
0.64
47.88
2678.00
8095.00
0.90
1.16
1.32
1.10
1.01
0.91
0.59
0.43
0.43
0.59
0.56
0.49
0.24
0.21
0.22
0.22
0.42
0.40
0.42
0.42
Notes
of such types of molecule, has excellent stability, even under a
higher working voltage, thereby delivering a relatively high
fluorescent brightness (Table 2). The maximum external
quantum efficiency of 0.59% is still much lower than the
theoretically evaluated value of ∼5% for an organic emitting
material with singlet excitation used, which might be further
improved by the rational molecular modification and
optimization of device fabrication.
In conclusion, we have constructed a highly efficient alkyne
benzannulation access to prepare the amino-substituted
dibenze[a,j]anthracence derivatives upon the activation of
Brønsted acid. These derivatives were concisely transformed to
new types of NBN-embedded PAHs through a nitrogen-
directed electrophilic borylation. The fully zigzag-edged
structure for such types of molecules was essentially confirmed
by single-crystal X-ray analysis. Their strong photolumines-
cence and highly reversible oxidation processes were also
clearly manifested. The blue−green electroluminescent device
using 5b as a dopant, exhibits a low relative low turn-on
voltage of 2.8 V, and a strong luminescence up to 8095 cd/m2,
demonstrating its excellent semiconducting characters. The
reported successive annulation might be widely suitable for the
formation of many complex PAHs with promising properties.
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
We thank Shanghai Committee of Science and Technology for
financial support within Project No. 16JC1400703. Further-
more, this work was financially supported by National Natural
Science Foundation of China (Nos. 21574080, 21774072,
21720102002). Open Project Program of the State Key
Laboratory of Inorganic Synthesis and Preparative Chemistry
(No. 2019-01, Jilin University). We acknowledge the
Instrumental Analysis Center of SJTU for the NMR, single-
crystal, and HRMS measurements.
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ASSOCIATED CONTENT
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S
* Supporting Information
The Supporting Information is available free of charge on the
Spectroscopic data for new compounds, experimental
and computational details, crystal structural data (PDF)
Accession Codes
CCDC 1912074 contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge
bridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: + 44 1223 336033.
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AUTHOR INFORMATION
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Corresponding Authors
Zhu).
Zhang).
ORCID
Author Contributions
‡These authors contributed equally to this work.
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