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yield: 93.5%). 1H NMR spectra of the target compound was not
obtained for its poor solubility in common solvent. HRMS (ESI,
m/z) calculated for C39H24N4O: 565.2028, found [M]+: 565.2050.
Anal. calcd for C39H24N4O: C 82.96, H 4.28, N 9.92. Found: C
82.61, H 3.90, N 9.72.
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6 B. W. D'Andrade and S. R. Forrest, Adv. Mater., 2004, 16,
1585–1595.
3-(Dibenzo[b,d]thiophen-4-yl)-9H-carbazole (5). The title
compound was synthesized according to the similar procedure
to 3, with the addition of dibenzo[b,d]thiophen-4-ylboronic acid
and the title compound was obtained as a white solid (yield:
7 S. Chen, L. Deng, J. Xie, L. Peng, L. Xie, Q. Fan and W. Huang,
Adv. Mater., 2010, 22, 5227–5239.
8 Y. Tao, C. Yang and J. Qin, Chem. Soc. Rev., 2011, 40, 2943–2970.
9 Y. Y. Lyu, J. Kwak, W. S. Jeon, Y. Byun, H. S. Lee, D. Kim,
C. Lee and K. Char, Adv. Funct. Mater., 2009, 19, 420.
1
97.2%). H NMR (400 MHz, CDCl3) d 8.45 (d, J ¼ 1.6 Hz, 1H),
8.24–8.11 (m, 4H), 7.85–7.80 (m, 2H), 7.59 (dd, J ¼ 10.4, 6.4 Hz, 10 P. I. Shih, C. H. Chien, C. Y. Chuang, C. F. Shu, C. H. Yang,
3H), 7.49–7.44 (m, 4H), 7.28 (dd, J ¼ 7.8, 1.6 Hz, 1H).
3-(Dibenzo[b,d]thiophen-4-yl)-9-(4,6-diphenyl-1,3,5-triazin-2- 11 Y. Tao, S. Gong, Q. Wang, C. Zhong, C. Yang, J. Qin and
yl)-9H-carbazole (BTTC). The title compound was synthesized D. Ma, Phys. Chem. Chem. Phys., 2010, 12, 2438.
according to the similar procedure to BFTC, with the addition of 12 F. M. Hsu, C. H. Chien, C. F. Shu, C. H. Lai, C. C. Hsieh,
intermediate 5 and the title compound was achieved as a white K. W. Wang and P. T. Chou, Adv. Funct. Mater., 2009, 19, 2834.
solid (yield: 89.7%). H NMR spectra of the target compound 13 Y. Tao, Q. Wang, C. Yang, J. Qin and D. Ma, ACS Appl. Mater.
was not obtained for its poor solubility in common solvent. Interfaces, 2010, 2, 2813.
J. H. Chen and Y. Chi, J. Mater. Chem., 2007, 17, 1692.
1
HRMS (ESI, m/z) calculated for C39H24N4S: 581.1800, found 14 X. L. Li, X. Ouyang, M. Liu, Z. Ge, J. Peng, Y. Cao and S. J. Su,
[M]+: 581.1796. Anal. calcd for C39H24N4S: C 80.67, H 4.17, N
9.65. Found: C 80.54, H 3.66, N 9.51.
J. Mater. Chem. C, 2015, 3, 9233.
15 K. P. Guo, H. D. Wang, Z. X. Wang, C. F. Si, C. Y. Peng,
G. Chen, J. H. Zhang, G. F. Wang and B. Wei, Chem. Sci.,
2017, DOI: 10.1039/c6sc03008d.
OLEDs fabrication
16 S. Lee, K. H. Kim, D. Limbach, Y. S. Park and J. J. Kim, Adv.
Funct. Mater., 2014, 24, 6074.
17 R. Keruckiene, D. Volyniuk, J. Ostrauskaite, L. Peciulyte,
J. V. Grazulevicius, S. V. Kostjuk and A. Lazauskas, Dyes
Pigm., 2016, 137, 58–68.
18 G. J. Tian, X. Wei, N. Xiang, J. H. Huang, J. Cao, Z. X. Wang,
J. H. Zhang and J. H. Su, RSC Adv., 2016, 6, 51575–51582.
19 Y. Chen, W. Q. Liang, W. H. Choi, J. H. Huang, Q. C. Dong,
F. R. Zhu and J. H. Su, Dyes Pigm., 2015, 123, 196–203.
20 F. Dumur, Org. Electron., 2015, 25, 345–361.
21 D. R. Lee, C. W. Lee and J. Y. Lee, J. Mater. Chem. C, 2014, 2,
7256.
All devices were encapsulated in a N2 purged glove box con-
nected to the evaporator aer the fabrication for device elec-
troluminescence characterization. The ITO/glass substrate was
cleaned sequentially by detergent, de-ionized water and
ethanol. Then the ITO/glass was treated by oxygen (O2) and
polymerized uorocarbon (CFx) plasma before loading into
a 10-source evaporator, with a base pressure of 5.0 ꢂ 10ꢀ4 Pa,
for device fabrication. Organic layers were deposited on the
indium-tin-oxide (ITO)/glass substrate by thermal evaporation.
Conclusion
22 H. F. Chen, S. J. Yang, Z. H. Tsai, W. Y. Huang, T. C. Wang
and K. T. Wong, J. Mater. Chem., 2009, 19, 8112–8118.
23 G. Hughes and M. R. Bryce, J. Mater. Chem., 2005, 15, 94.
24 S. M. Kim, S. Y. Byeon, S. H. Hwang and J. Y. Lee, Chem.
Commun., 2015, 51, 10672–10675.
25 D. Wanger, S. T. Hoffmann, U. Heinemeyer, I. Munster,
A. Kohler and P. Strohriegl, Chem. Mater., 2013, 25, 3758–3765.
26 S. J. Su, C. Cai, J. Takamatsu and J. Kido, Org. Electron., 2012,
13, 1937–1947.
27 C. H. Chang, M. C. Kuo, W. C. Lin, Y. T. Chen, K. T. Wong,
S. H. Chou, E. Mondal, R. C. Kwong, S. Xia, T. Nakagawa
and C. Adachi, J. Mater. Chem., 2012, 22, 3832.
28 J. S. Kang, T. R. Hong, H. J. Kim, Y. H. Son, R. Lampande,
B. Y. Kang, C. Lee, J. K. Bin, B. S. Lee, J. H. Yang,
J. W. Kim, S. Park, M. J. Cho, J. H. Kwon and D. H. Choi, J.
Mater. Chem. C, 2016, 4, 4512.
In summary, two novel bipolar host materials, BFTC and BTTC
are synthesized and characterized, and electroluminescence
performance of green PhOLED based on those two host mate-
rials are investigated. Eventually, BTTC demonstrates its
promising potential as a desirable host material for green
PHOLED with a high Td of 452 ꢁC. The green PhOLEDs based on
those host materials with the structure of ITO/PEDOT:PSS/
TAPC/TCTA/host: Ir(ppy)3 (8 wt%)/TPBi/LiF/Al show superior
electroluminescence performance, with the turn-on voltage of
3.4 V and maximum current, power and external quantum
efficiency of 69.3 cd Aꢀ1, 54.2 lm Wꢀ1 and 21.9%, respectively.
Notes and references
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7292 | RSC Adv., 2017, 7, 7287–7292
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