Highly Efficient Blue Light-Emitting Diodes Based on Diarylanthracene/Triphenylsilane Compounds
Park et al.
2. EXPERIMENTAL DETAILS
(75 MHz, CDCl3) [ꢄ ppm]: 154.6, 153.5, 140.8, 138.8,
138.6, 138.0, 137.2, 136.8, 135.8, 134.8, 133.7, 133.3,
133.0, 130.7, 130.5, 130.4, 130.3, 129.9, 128.4, 128.2,
127.4, 126.7, 126.5, 126.1, 125.4, 120.5, 119.9, 47.4, 27.5.
FT-IR [ATR]: ꢅ = 3067, 2969, 1738, 1429, 1110, 819, 766,
746, 701 cm−1. EI-MS (m/z): 754 [M+]; HRMS: [EI+]
calcd for C57H42Si: 754.3056, [M+]. Found: 754.3065.
2.1. Material and Measurements
All reactions were performed under nitrogen. Solvents
were carefully dried and distilled from appropriate drying
agents prior to use. 4ꢀ-[2-(2-Diphenylamino-9,9-diethyl-
9H-fluoren-7-yl)vinyl]-p-terphenyl (PFVtPh) and 3-(N-
phenylcarbazol)vinyl-p-terphenyl (PCVtPh) were prepared
by a method previously reported.13
2.3. Physical Measurements
1H- and 13C-NMR were recorded on a Varian Unity
Inova 300Nb spectrometer. FT-IR spectra were recorded
using a Bruker VERTEX70 FT-IR spectrometer. Low-
resolution mass spectra were measured using a Jeol
JMS-AX505WA spectrometer in the FAB mode or a Jeol
JMS-600 spectrometer in the EI mode.
The UV-Vis absorption and photoluminescence spectra of
these newly designed host materials were measured in
CH2Cl2 (10−5 M) using a Shimadzu UV-1650PC and an
Amincobrowman series 2 luminescence spectrometer. The
fluorescent quantum yields were determined in the CH2Cl2
solution at 293 K against the host (ꢆDPA = 0ꢀ90) as a
reference. The energy levels were measured with a low-
energy photo-electron spectrometer (Riken-Keiki, AC-2).
Thermal properties were measured using thermogravimet-
ric analysis (TGA) (Seiko, TG/DTA 320) under nitrogen
2.2. General Procedure for the Suzuki
Cross-Coupling Reaction
10-(Naphthalen-2-yl)anthracen-9-yl-boronic acid (1.2 mol)
and the corresponding triphenylsilyl bromide derivatives
(1.0 mol), Pd(PPh3ꢂ4 (0.04 mol), aqueous 2.0 M Na2CO3
(10.0 mol), ethanol, and toluene were mixed in a flask. The
mixture was refluxed for 4 h. After the reaction had fin-
ished, the reaction mixture was extracted with ethyl acetate
and washed with water. The organic layer was dried with
ꢁ
at a heating rate of 10 C/min.
2.4. OLED Fabrication and Measurement
For fabricating OLEDs, indium-tin-oxide (ITO) thin
films coated on glass substrates were used, which was
30 ꢇ/square of the sheet resistivity, and 1000 Å of thick-
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anhydrous MgSO4 and filtered with silica gel. The solution
ness. The ITO-coated glass was cleaned in an ultrasonic
IP: 91.242.217.252 On: Sat, 11 Jun 2016 10:14:39
was then evaporated. The crude product was then recrys-
tallized from CH2Cl2/EtOH and then purified further by
train sublimation at the reduced pressure.
Copyright: American Scientific Publishers
bath by the following sequence: acetone, methyl alco-
hol, distilled water, and stored in isopropyl alcohol for
48 h and dried by a N2 gas gun. The substrates were
treated by O2 plasma under 2ꢀ0 × 10−2 torr at 125 W for
2 min.14 All organic materials and metals were deposited
under high vacuum (5×10−7 torr). The OLEDs were fabri-
cated in the following sequence: ITO/N,Nꢀ-diphenyl-N,Nꢀ-
(1-napthyl)-(1,1ꢀ-phenyl)-4,4ꢀ-diamine (NPB) (500 Å)/Blue
host materials (ANPTPS and ANFTPS): Blue dopant mate-
rials (PFVtPh and PCVtPh) (300 Å, 8%)/4,7-diphenyl-
1,10-phenanthroline (Bphen) (300 Å)/lithium quinolate
(Liq) (20 Å)/Al (1000 Å). The devices were fabricated with
the same configurations, except employing 8% PFVtPh
and PCVtPh as a dopant within ANPTPS and ANFTPS
as a host in the emitting layers. The current density (J),
luminance (L), luminous efficiency (LE), and CIE chro-
maticity coordinates of the OLEDs were measured with a
Keithly 2400, Chroma meter CS-1000A. Electroluminance
was measured using a Roper Scientific Pro 300i.
2.2.1. (4-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)
triphenylsilane (ANPTPS)
1
Yield: 70%, H-NMR (300 MHz, CDCl3) [ꢄ ppm]: 8.06
(d, J = 8ꢀ1 Hz, 1H), 8.03–8.00 (m, 1H), 7.98 (s, 1H), 7.92–
7.89 (m, 1H), 7.83 (d, J = 8ꢀ4 Hz, 2H), 7.77–7.71 (m, 9H),
7.62–7.55 (m, 4H), 7.54–7.43 (m, 10H), 7.38–7.27
(m, 5H). 13C-NMR (75 MHz, CDCl3) [ꢄ ppm]: 140.7,
137.3, 137.2, 136.8, 136.7, 134.5, 133.7, 133.6, 133.0,
131.1, 130.5, 130.3, 130.0, 129.9, 129.8, 128.4, 128.3,
128.2, 128.1, 127.3, 126.7, 126.5, 125.4. FT-IR [ATR]:
ꢅ = 3066, 1428, 1109, 818, 766, 745, 702 cm−1. FAB-
MS (m/z): 638 [M+]; HRMS: [EI+] calcd for C48H34Si:
638.2430, [M+]. Found: 638.2438.
2.2.2. 9,9-dimethyl-7-(10-(naphthalen-2-yl)
anthracen-9-yl)-9H-fluoren-2-yl)triphenylsilane
(ANFTPS)
3. RESULTS AND DISCUSSION
1
Yield: 60%, H-NMR (300 MHz, CDCl3) [ꢄ ppm]: 8.08
Scheme 1 shows the Synthesis of the newly designed
host compounds and the structure of dopant compounds.
The host compounds were synthesized via Suzuki Cross-
Coupling reactions with moderate yields. All the obtained
compounds were characterized by 1H- and 13C NMR,
(d, J = 8ꢀ4 Hz, 1H), 8.05–7.97 (m, 3H), 7.94–7.91
(m, 1H), 7.86 (d, J = 7ꢀ2 Hz, 1H), 7.82–7.79 (m, 2H),
7.75–7.71 (m, 3H), 7.66–7.58 (m, 11H), 7.50–7.37
(m, 10H), 7.35–7.30 (m, 4H), 1.53 (s, 6H). 13C-NMR
4358
J. Nanosci. Nanotechnol. 11, 4357–4362, 2011