Blue OLEDs Containing Anthracene
175
potassium iodide (2.77 g, 16.69 mmol), sodium hypophosphite monohydrtate (2.77 g,
1.53 mmol), and acetic acid (22 mL), and the mixture was heated under reflux for 3 h.
3
After cooling, the precipitate was collected, washed with plenty of distilled water, and dried.
Concentration of the CH2Cl2 solution, followed by column chromatography on silica gel
1
with CH2Cl2/hexane, afforded 2 (1.58g, 89.0%). H-NMR (300 MHz, CDCl3) [δ ppm]:
7
2
1
3
3
.71–7.67 (m, 3H), 7.64–7.54 (m, 7H), 7.50–7.45 (m, 4H), 7.42 (s, 1H), 7.32–7.28 (m,
H), 1.26 (s, 9H). 13C-NMR (75 MHz, CDCl3) [δ ppm]: 147.5, 139.5, 137.1, 136.9, 131.6,
30.3, 129.8, 128.7, 128.6, 128.5, 127.6, 127.2, 126.9, 125.1, 124.9, 124.8, 121.4, 35.2,
−1
+
1.0. FT-IR [ATR]: ν 3709, 3680, 2981, 2971, 1738, 1365, 1055, 700 cm MS(EI ) m/z
+
86 (M ). Anal. calcd for C30H26: C 93.22, H 6.78; found: C 92.67, H 7.03.
ꢀ
ꢀ
ꢀ
ꢀ
1
0,10 -Diphenyl-9,9 -bianthryl (3): 10,10 -dibromo-9,9 -bianthryl (1.2 g, 2.34 mmol)
and phenyl boronic acid (0.85 g, 7.02 mmol), Pd(PPh3)4 (0.41 g, 0.35 mmol), aqueous
.0 M Na2CO3 (2.48 g, 22.8 mmol), and toluene (24 ml) were mixed in a flask. The mixture
2
was refluxed for 4 h. When the reaction was completed, water was added to quench the
reaction. After cooling, the crude solid was collected by filtration, washed with water, and
ethanol. The product was recrystallized from CH2Cl2/EtOH, afforded 3 (0.8 g, 67.8%).
1
H-NMR (300 MHz, CDCl3) [δ ppm]: 7.82 (d, J = 8.7 Hz, 4H), 7.69–7.59 (m, 10H),
13
7
.32 (td, J = 1.2, 7.7 Hz, 4H), 7.25 (d, J = 8.4 Hz, 4H), 7.17–7.12 (m, 4H). C-NMR
(75 MHz, CDCl3) [δ ppm]: 139.3, 138.1, 133.7, 131.7, 131.6, 130.4, 128.7, 127.8, 127.5,
−1
+
1
5
27.4, 125.8, 125.5. FT-IR [ATR]: ν 3062, 1739, 1441, 1363, 768, 706 cm MS(EI ) m/z
+
06 (M ). Anal. calcd for C40H26: C 94.83, H 5.17; found: C 93.40, H 5.30.
1
,4-Bis(10-phenylanthracen-9-yl)benzene (4): 1,4dibromobenzene (1 g, 4.23 mmol)
and 10-phenylanthracen-9-yl boronic acid (2.7 g, 9.32 mmol), Pd(PPh3)4 (0.20 g,
.17 mmol), aqueous 2.0 M Na2CO3 (4.49 g, 42.39 mmol), ethanol (21 ml) and toluene
42 ml) were mixed in a flask. The mixture was refluxed for 3 h. When the reaction was
0
(
completed, water was added to quench the reaction. After cooling, the crude solid was
collected by filtration, washed with water, and ethanol. The product was recrystallized
1
from CH2Cl2/EtOH, afforded 4 (2.1 g, 85.4%). H-NMR (300 MHz, CDCl3) [δ ppm]: 7.99
(
d, J = 8.7 Hz, 4H), 7.76 (t, J = 8.7 Hz, 2H), 7.74 (s, 4H), 7.68–7.59 (m, 8H), 7.55 (dd,
J = 1.5, 8.0 Hz, 4H), 7.50–7.48 (m, 4H), 7.44–7.39 (m, 4H). FT-IR [ATR]: ν 3061, 2360,
−1
+
+
+
2
341, 1736, 1440, 1368, 764, 702 cm MS(EI ) m/z 582 (M ). HRMS-TOF (M +H)
Anal. calcd for C48H32N 583.242576: found: 583.23936. Anal. calcd for C46H30: C 94.81,
H 5.19; found: C 93.58, H 5.29.
Fabrication of OLED
−6
OLEDs using red-light-emitting molecules were fabricated by vacuum (10 torr) thermal
evaporation onto pre-cleaned ITO coated glass substrates. All processes were carefully pro-
duced. The indium tin oxide (ITO) was first cleaned with acetone, methyl alcohol, distilled
water, and kept in isopropyl alcohol for 48 h and dried by N2 gas. The substrates were
−
2
treated by O2 plasma under 2.0 × 10 torr at 125 W for 2 min [18]. All organic materials
−7
and metals were deposited under high vacuum (5 × 10 torr). The OLEDs were fabricated
ꢀ
in the following sequence: ITO/4,4 -Bis(N-(1-naphthyl)-N-phenylamino)biphenyl (NPB)
(
(
50 nm)/Blue emitting materials (1–4) (30 nm)/4,7-Diphenyl-1,10-phenanthroline (Bphen)
30 nm)/Lithium quinolate (Liq) (2 nm)/Al (100 nm), NPB as the hole-transporting layer,
Bphen as the electron-transporting layer, and Liq:Al as the composite cathode. The current
density (J), luminance (L), luminous efficiency (LE), and CIE chromaticity coordinates of