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Journal of Materials Chemistry C
Page 10 of 12
DOI: 10.1039/C5TC03749B
ARTICLE
Journal Name
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Synthesis of 6,12-bis[4-(diphenylamino)phenyl]chrysene,
TPA-C-TPA [13]
Compound [5] (1.13 g, 3.9 mmol), Pd(PPh3)4 (0.12g, 0.11
mmol) were added to 200 mL of dry toluene solution. Then,
6,12-dibromo-chrysene (0.5g, 1.3 mmol) and 2M K2CO3
solution (10 mL), which was dissolved in H2O, was added to the
reaction mixture. The reaction mixture was heated to 110°C
for 7h under nitrogen. After the reaction was finished, diethyl
ether and water were extracted. The organic layer was dried
with anhydrous MgSO4 and filtered. The solvent was
evaporated. The product was isolated by silica gel column
chromatography using CHCl3: hexane (1 : 2) eluent to afford a
white solid. (Yield 56%) 1H NMR (300MHz, [D8]THF 25°C, TMS):
δ=9.00 (d, 2H), 8.77 (s, 2H), 8.13 (d, 2H), 7.69 (t, 2H), 7.54 (m,
6H), 7.30 (m, 10H), 7.21 (m, 10H), 7.04 ppm (t, 4H). EI+-Mass:
714, Anal. calcd for C84H38N2: C 90.72, H 5.36, N 3.92; found: C
90.67, H 5.33, N 3.97%.
Jing and F. Wang, J. Mater. Chem. C, 2015,
S. Wang, S. Shao, J. Ding, L. Wang, X. Jing and F. Wang, J.
Mater. Chem. C, 2015, , 8859.
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Conclusions
The chrysene group, with its large band gap, was selected as
a central core structure for designing new molecules that emit
ultra-deep-blue light with high efficiency. The effects of
different side groups on the intrinsic properties of the
chrysene core were systematically investigated. As a result, the
oscillator strength of the chrysene core molecule was
increased by selecting an appropriate side group, and an
improved PLQY value was obtained. Also, the substitution of
electron-donating side groups into the chrysene core was
shown to affect the optical and physical properties of the
molecule. The synthesized materials were applied as EMLs in
non-doped devices, and the TP-C-TPB device afforded efficient
ultra-deep-blue emission below the HDTV standard blue (CIE y
0.06), with an EQE of 4.02% and excellent color coordinates of
3
4
5
6
CIE x,y (0.151, 0.042). In addition, TPA-C-TPA
, which
introduced triphenylamine with hole-transporting properties,
exhibited a low operating voltage and an excellent EQE of
4.83%, while showing color coordinates of CIE x,y (0.147,
0.077), below NTSC blue (CIE y 0.08). Such results for
molecules based on the chrysene core with its large band gap
are expected to help the development of materials that can
maintain a highly efficient emission of deep-blue light.
The conclusions section should come in this section at the end
of the article, before the acknowledgements.
7
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Acknowledgements
Development Program for Strategic Core Materials funded by
the Ministry of Trade, Industry & Energy, Republic of Korea
(Project No. 10047758).
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Notes and references
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Funct. Mater., 2011, 21, 699.
10 | J. Name., 2012, 00, 1-3
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