An Efficient Pure Blue Organic Light-Emitting Device with Low Driving Voltages

A series of 2,8‐disubstituted dibenzothiophene and 2,8‐disubstituted dibenzothiophene‐S,S‐dioxide derivatives containing quinoxaline and pyrazine moieties are synthesized via three key steps: i) palladium‐catalyzed Sonogashira coupling reaction to form dialkynes; ii) conversion of the dialkynes to diones; and iii) condensation of the diones with diamines. Single‐crystal characterization of 2,8‐di(6,7‐dimethyl‐3‐phenyl‐2‐quinoxalinyl)‐5H‐5λ6‐dibenzo[b,d]thiophene‐5,5‐dione indicates a triclinic crystal structure with space group P1 and a non‐coplanar structure. These new materials are amorphous, with glass‐transition temperatures ranging from 132 to 194 °C. The compounds (Cpd) exhibit high electron mobilities and serve as effective electron‐transport materials for organic light‐emitting devices. Double‐layer devices are fabricated with the structure indium tin oxide (ITO)/Qn/Cpd/LiF/Al, where yellow‐emitting 2,3‐bis[4‐(N‐phenyl‐9‐ethyl‐3‐carbazolylamino)phenyl]quinoxaline (Qn) serves as the emitting layer. An external quantum efficiency of 1.41 %, a power efficiency of 4.94 lm W–1, and a current efficiency of 1.62 cd A–1 are achieved at a current density of 100 mA cm–2.

Section: Charge-transport Propertiessupporting

confidence: 86%

Dibenzothiophene/Oxide and Quinoxaline/Pyrazine Derivatives Serving as Electron‐Transport Materials

Huang

Whang

Shen

et al. 2006

“…10 -3 cm 2 V -1 s -1 ). [21] The relatively high electron mobilities observed for 2,7-disubstituted carbazoles (7, ca. 10 -4 cm 2 V -1 s -1 ; 9, ca.…”

Section: Charge-transport Propertiesmentioning

confidence: 99%

Ambipolar Conductive 2,7‐Carbazole Derivatives for Electroluminescent Devices

Shen

Yang

Huang

et al. 2007

A series of 2,7‐disubstituted carbazole (2,7‐carb) derivatives incorporating arylamines at the 2 and 7 positions are synthesized via palladium‐catalyzed C–N or C–C bond formation. These compounds possess glass transition temperatures ranging from 87 to 217 °C and exhibit good thermal stabilities, with thermal decomposition temperatures ranging from 388 to 480 °C. They are fluorescent and emit in the purple‐blue to orange region. Two types of organic light emitting diodes (OLEDs) were constructed from these compounds: (I) indium tin oxide (ITO)/2,7‐carb (40 nm)/1,3,5‐tris(N‐phenylbenzimidazol‐2‐yl)benzene (TPBI, 40 nm)/Mg:Ag; and (II) ITO/2,7‐carb (40 nm)/tris(8‐hydroxyquinoline) aluminum (Alq3, 40 nm)/Mg:Ag. In type I devices, the 2,7‐disubstituted carbazoles function as both hole‐transporting and emitting material. In type II devices, light is emitted from either the 2,7‐disubstituted carbazole layer or Alq3. The devices appear to have a better performance compared to devices fabricated with their 3,6‐disubstituted carbazole congeners. Some of the new compounds exhibit ambipolar conductive behavior, with hole and electron mobilities up to 10–4 cm2 V–1 s–1.

“…On the other hand, the migration of electrons from TPBI to the LUMO of 4 and to ITO is expected to proceed smoothly in view of the high LUMO and the great electron-injection ability of the TPBI layer [31] and the low LUMO of 4. As a result, electron leaking from 4 to the ITO layer is high and the probability of trapping both electron and hole in the layer of compound 4 is low resulting in a poor efficiency of device A.…”

Section: Full Papermentioning

confidence: 99%

Luminescence Properties of Aminobenzanthrones and Their Application as Host Emitters in Organic Light‐Emitting Devices

Chang

Lin

et al. 2007

A series of aminobenzanthrone derivatives, possessing a keto and an amino group on the aromatic ring, are synthesized and their photoluminescence (PL) and electroluminescence (EL) properties are studied in detail. These compounds emit strongly in solution and in the solid state, with the emission maxima in the range of 528–668 nm resulting from charge‐transfer transitions from the amino group to the keto moiety. The emission wavelength depends greatly on the polarity of the solvent. A red shift of nearly 100 nm is observed from n‐hexane to dichloromethane for each of these compounds. The PL quantum yields of these molecules also depend tremendously on the solvent. The values are between 88 and 70 % in n‐hexane and decrease as the polarity of the solvent increases. The single‐crystal X‐ray diffraction data reveal that the aminobenzanthrone planes of these molecules stack in the crystals in an antiparallel head‐to‐tail fashion. This strong dipole–dipole interaction accounts for the observed red‐shifted emissions of the aminobenzanthrone molecules in powders and in films relative to those in nonpolar solvents. Electroluminescent devices using aminobenzanthrone derivatives as the host emitters or dopants emit orange to red light in the range 590–645 nm. High brightness, current efficiency, and power efficiency are observed for some of these devices. For example, the device using N‐(4‐t‐butylphenyl)‐N‐biphenyl‐3‐benzanthronylamine as the emitter gives saturated red light with a current efficiency of 1.82 cd A–1, brightness of 11 253 cd m–2, and Commission Internationale de l'Éclairage (CIE) coordinates of (0.64,0.36); the device using N‐(2‐naphthyl)‐N‐phenyl‐3‐benzanthronylamine as the emitter gives orange–red light with a current efficiency of 3.52 cd A–1, brightness of 25 000 cd m–2, and CIE coordinates of (0.61,0.38).