Red Phosphorescent Bis-Cyclometalated Iridium Complexes with Fluorine-, Phenyl-, and Fluorophenyl-Substituted 2-Arylquinoline Ligands.

Red phosphorescent iridium(III) complexes based on fluorine-, phenyl-, and fluorophenyl-substituted 2-arylquinoline ligands were designed and synthesized. To investigate their electrophosphorescent properties, devices were fabricated with the following structure: indium tin oxide (ITO)/4,4',4''-tris[2-naphthyl(phenyl)amino]triphenylamine (2-TNATA)/4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB)/4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP): 8% iridium (III) complexes/bathocuproine (BCP)/tris(8-hydroxyquinolinato)aluminum (Alq3)/8-hydroxyquinoline lithium (Liq)/Al. All devices, which use these materials showed efficient red emissions. In particular, a device exhibited a saturated red emission with a maximum luminance, external quantum efficiency, and luminous efficiency of 14200 cd m(-2), 8.44%, and 6.58 cd A(-1) at 20 mA cm(-2), respectively. The CIE (x, y) coordinates of this device are (0.67, 0.33) at 12.0 V.

Red fluorescent materials based on julolidine/chromene with the bulky tert-butyl and trimethylsilyl substituents for organic light-emitting diodes.

In this work, we designed and synthesized two red emitters 2-(6,8-di-tert-butyl-2-(2-(1,1-dimethyl-7-(trimethylsilyl)-7-((trimethylsilyl)methyl)-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolin-9-yl)vinyl)-4H-chromen-4-ylidene)malononitrile (Red 1) and 2-(6,8-di-tert-butyl-2-(2-(1,1,7-trimethyl-7-t-butyl)-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolin-9-yl)vinyl)-4H-chromen-4-ylidene)malononitrile (Red 2). To explore the electro-luminescence properties of these materials, multilayered OLEDs using these materials as dopants in a Alq3 host were fabricated. Particularly, by using Red 1 as a dopant in emitting layer, device 1 showed the luminous and power efficiencies of 0.81 cd/A and 0.43 lm/W at 20 mA/cm2, respectively. The CIE coordinates of this device was (0.65, 0.34) at 7.0 V, which is close to the NTSC standard CIE coordinates of (0.67,0.32) for red emission.

Blue organic light-emitting diodes based on new bipolar anthracene derivatives containing pyridine.

A series of bipolar anthracene derivatives containing pyridine as an electron withdrawing group and cabazole, triphenylamine and indole as electron donating groups were synthesized and characterized. Particularly, Device E, 9-(4'-(10-(pyridin-2-yl)anthracen-9-yl)biphenyl-4-yl)-9H-carbazol exhibits a high-efficient deep-blue EL emission with the luminous efficiency (LE) of 2.31 cd/A, power efficiency (PE) of 1.39 lm/W and quantum efficiency (QE) of 1.94% at 500 nit. This compound shows the maximum wavelength of the electroluminescence (EL) at 467 nm and the CIE x, y coordinates of (0.16,0.14) at 6 V.

Triphenylamine substituted anthracene derivatives for blue organic light-emitting diodes.

A series of bipolar anthracene derivatives containing triphenylamine as an electron donating group and pyridine, quinoline, isoquinoline and benzothiazole as electron withdrawing groups were synthesized and characterized. Particularly, a material, 9-quinolinyl-10-triphenylamin anthracene (3) exhibits a highly efficient sky-blue EL emission with the luminous efficiency (LE) of 9.36 cd/A, power efficiency (PE) of 5.94 lm/W and quantum efficiency (QE) of 4.23% at 500 nit. This material shows the maximum wavelength of the electroluminescence (EL) at 486 nm and the CIE x, y coordinates of (0.17, 0.36) at 6 V.

Undoped blue organic light-emitting diodes using 2-diphenylaminofluoren-7-ylstyryl derivatives.

Blue fluorescent materials based on diphenylaminofluorenylstyryl derivatives connected with the various end-capping aromatic groups were synthesized and characterized. An OLED, using (E)-9,9-diethyl-7-(4-(4-fluoronaphthalen-1-yl)styryl)-N,N-diphenyl-9 H-fluoren-2-amine(5) in emitting layer, was fabricated. This device showed the highly efficient blue emission with the maximum luminance of 5138 cd/m2, the luminous efficiency of 3.92 cd/A, the power efficiency of 3.17 lm/W, the external quantum efficiency of 2.90% at 20 mA/cm2 and CIE x, y coordinates of (0.14, 0.17).

N,N-(diphenylamino)fluorenylstyrene derivatives with the various heteroatom-containing moieties for blue organic light-emitting diodes.

A series of blue fluorescent materials 1-6 based on N, N-diphenyl aminofluorene styryl derivatives with six heteroatoms (PhOPh, PhSPh, PhSePh, PhPPh2, thiophene and dibenzothiophene), were synthesized and multilayer devices were fabricated. Interestingly, the EL efficiencies were very sensitive to the structural features of dopants in the emitting layers. Particularly, by using 1 as a dopant in emitting layer, a high-efficiency blue OLED was fabricated, showing the maximum luminance of 10420 cd/m2 at 11 V, the luminous efficiency of 8.6 cd/A at 20 mA/cm2, the power efficiency of 3.4 Im/W at 20 mA/cm2 and had a blue color with the CIE coordinates of (0.147, 0.156) at 8.0 V.

Red fluorescent emitting materials based on di-tert-butyl chromene derivatives for organic light-emitting diodes.

In this paper are described two di-tert-butyl chromene-containing red fluorescent materials (Red 1 and Red 2). To explore the electroluminescence properties of these materials, multilayered OLEDs using these materials as dopants in a Alq3 host were fabricated. In particular, a device using Red 2 as the dopant material showed maximum luminous efficiencies and power efficiencies of 1.14 cd/A and 0.58 Im/W, respectively. The CIEx,y coordinates of this device were (0.67, 0.32) at 7.0 V.

Phosphorescence white organic light-emitting diodes with single emitting layer based on isoquinolinefluorene-carbazole containing host.

We have demonstrated a stable phosphorescent white organic light-emitting diodes (WOLEDs) using an orange emitter, Bis(5-benzoyl-2-(4-fluorophenyl)pyridinato-C,N) iridium(III)acetylacetonate [(Bz4Fppy)2Ir(III)acac] doped into a newly synthesized blue host material, 2-(carbazol-9-yl)-7-(isoquinolin-1-yl)-9,9-diethylfluorene (CzFliq). When 1 wt.% (Bz4Fppy)2Ir(III)acac was doped into emitting layer, it was realized an improved EL performance and a pure white color in the OLED. The optimum WOLED showed maximum values as a luminous efficiency of 10.14 cd/A, a power efficiency of 10.24 Im/W, a peak external quantum efficiency 4.07%, and Commission Internationale de L'Eclairage coordinates of (0.34, 0.39) at 8 V.

Efficient green phosphorescent organic light-emitting diodes depending on concentration of lithium quinolate in electron transport layer.

Systematic studies on carrier injection and transport are very important for achieving high efficiency in OLEDs. We demonstrate excellent green phosphorescent organic light-emitting diodes (OLED) with lithium quinolate (Liq) doped in 1,3,5-tris(N-phenylbenzimidazole-2-yl) benzene (TPBi) as the electron transport layer (ETL). The doping concentration of Liq was varied from 0% to 10%. The optimized green phosphorescent OLED with 5% Liq in the ETL showed the best efficiencies, which were maximum luminous efficiency, power efficiency, and quantum efficiency of 65.76 cd/A, 57.39 Im/W, and 20.03%, respectively. Moreover, high triplet energy states of TCTA and TPBi as a triplet exciton-blocking layer (TEBL) played a role in efficient exciton confinement.

Trimethylsilane-containing donor-acceptor-donor type material for red fluorescent organic light-emitting diodes.

In this paper, we described a donor-acceptor-donor type red fluorescence material, which have the bulky trimethylsilane groups in the donor moieties. To explore the electroluminescence properties of these materials, multilayered OLEDs were fabricated with a device structure of ITO/2-TNATA (60 nm)/NPB (40 nm)/Red 1 (2%):rubrene (50%):Alq3 (30 nm)/Alq3 (60 nm)/Liq (3 nm)/Al (100 nm). A device using Red 1 as the dopant material showed a maximum luminance of 5138 cd/m2 at 12.0 V, maximum luminous efficiencies of 1.62 cd/A, and maximum power efficiencies of 1.04 lm/W. The Commission Internationale de L'Eclairage coordinates of this device was (0.67, 0.33) at 7.0 V, which indicated stable color chromaticity at various voltages.

Diphenylamino-fluorenylethylene derivatives for highly efficient blue organic light-emitting diodes.

Highly efficient blue organic light-emitting diodes (OLEDs) were developed using diphenylamino-fluorenylethylene derivatives. In particular, OLEDs using compound 3 as a dopant in the emitting layer showed a maximum luminance of 12940 cd/m2 at 10 V; a luminous efficiency of 12.68 cd/A at 20 mA/cm2; a power efficiency of 5.24 Im/W at 20 mA/cm2, and CIE(x,y) coordinates of 0.181, 0.295 at 10 V. Furthermore, a deep blue OLED using dopant 2 with CIE coordinates of (0.154, 0.129) exhibited a maximum luminance of 5315 cd/m2 at 10 V; a luminous efficiency of 4.11 cd/A at 20 mA/cm2, and a power efficiency of 1.66 Im/W at 20 mA/cm2.

Efficient triplet exciton confinement of blue- and white-organic light emitting diodes using a new host material.

We have demonstrated lower driving voltage and efficient blue phosphorescent organic light emitting diodes (PHOLEDs) using iridium(III) bis[(4,6-di-fluoropheny)-pyridinato-N,C2] picolinate (Flrpic) doped in new host material 9-(4-(triphenylsilyl)phenyl)-9H-carbazole (SPC) and 2,2',2"-(1,3,5-benzenetryl)tris(1-phenyl)-1H-benzimidazol (TPBi) as double-emitting layer (D-EML) system. The D-EML was employed to have good electron transportability and exciton confinement. Additionally, we fabricated white organic light-emitting diode (WOLED) using a phosphorescent red emitter; bis(2-phenylquinolinato)-acetylacetonate iridium III (Ir(pq)2acac) doped in SPC and TPBi as D-EML. The properties of white device exhibited a maximum luminous efficiency of 19.03 cd/A, a maximum external quantum efficiency of 9.91%, and a maximum power efficiency of 12.30 lm/W. It also showed white emission with CIE(x,y) coordinates of (x = 0.38, y = 0.37) at 8 V.

White organic light-emitting diodes for emotion solid-state lighting.

The authors have demonstrated white organic light-emitting diodes for emotion solid-state lighting (ESSL) by using hole modulating layer (HML), N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine and N,N'-bis-(1-naphyl)-N,N'-diphenyl-1,1'-biphenyl-4, 4'-diamine, and mixed spacer (MS), 4,4',4"-tris(N-carbazolyl)-triphenylamine and {9,9-dimethyl-7-[10-(naphthalen-2-yl)anthracen-9-yl]-9H-fluoren-2-yl}triphenylsilane, respectively. The HML and MS were used for unbalance of holes and electrons. The ESSL showed various white light chromaticities of Commission Internationale de l'Eclairage coordinates from (0.46,0.42) as warm white emission to (0.29, 0.36) as cold white emission.

Orange-red phosphorescent OLEDs using iridium(III) complexes with benzoylphenylpyridine ligands containing fluorine and trifluoromethyl groups.

We have designed and synthesized four orange-red phosphorescent Ir(III) complexes based on the benzoylphenylpyridine ligand with fluorine and trifluoromethyl substitution. Multilayered OLEDs were fabricated using these complexes as dopant materials. Particularly, by using 1 as a dopant in the emitting layer, a highly efficient orange-red OLED was fabricated, showing a maximum luminance of 10410 cd/m2 at 10 V, a luminous efficiency of 17.47 cd/A, a power efficiency of 7.19 Im/W, an external quantum efficiency of 6.27% at 20 mA/cm2, respectively, and CIE(x,y) coordinates of (0.51, 0.48) at 10 V. Furthermore, a red OLED using dopant 2, with CIE(x,y) coordinates of (0.61, 0.39), exhibited a maximum luminance of 5797 cd/m2 at 10 V, a luminous efficiency of 11.43 cd/A at, a power efficiency of 4.12 Im/W, and an external quantum efficiency of 6.62% at 20 mA/cm2, respectively.

Efficient deep-blue organic light-emitting diodes using double-emitting layer.

Efficient deep-blue organic light-emitting diodes were demonstrated using 1,4-tetranaphthalene doped in double-emitting layers (D-EMLs) consisting of 2-methyl-9,10-di(2-naphthyl)anthracene and 4'-(dinaphthalen-2-yl)-1,1'-binaphthyl as blue hosts. The device with D-EML exhibits good confinement of holes and electrons, as well as a broad recombination zone. The optimized device showed a peak current efficiency of 3.67 cd/A, a peak external quantum efficiency of 3.97%, and Commission Internationale de L'Eclairage coordinates of (0.16, 0.10).

Highly efficient red phosphorescent organic light-emitting devices using iridium(III) complexes based on 2-(biphenyl-3-yl)quinoline derived ligands.

Red phosphorescent emitters were synthesized based on Ir(III) phenylquinoline complexes for applications to OLEDs. Ir(III) complexes 1-3 were based on 2-(biphenyl-3-yl)-quinoline units connected to various phenyl groups such as 5-phenyl, 5-(4-fluorophenyl), and 6-phenyl groups. The EL efficiencies were quite sensitive to the structural features of the dopants in the emitting layers. In particular, a high-efficiency red OLED was fabricated using complex 1 as the dopant in the emitting layer. This OLED showed a maximum luminance, luminous efficiency, power efficiency, external quantum efficiency and CIE(x,y) coordinates of 21,600 cd/m2 at 16 V, 11.80 cd/A at 20 mA/cm2, 3.57 Im/W at 20 mA/cm2, 10.90% at 20 mA/cm2, and (x = 0.63, y = 0.32) at 12 V, respectively.

Red phosphorescent organic light-emitting diodes based on the simple structure.

We demonstrated that the simple layered red phosphorescent organic light-emitting diodes (OLEDs) are possible to have high efficiency, low driving voltage, stable roll-off efficiency, and pure emission color without hole injection and transport layers. We fabricated the OLEDs with a structure of ITO/CBP doped with Ir(pq)2(acac)/BPhen/Liq/Al, where the doping concentration of red dopant, Ir(pq)2(acac), was varied from 4% to 20%. As a result, the quantum efficiencies of 13.4, 11.2, 16.7, 10.8 and 9.8% were observed in devices with doping concentrations of 4, 8, 12, 16 and 20%, respectively. Despite of absence of the hole injection and transport layers, these efficiencies are superior to efficiencies of device with hole transporting layer due to direct hole injection from anode to dopant in emission layer.

Enhancing Horizontal Ratio of Transition Dipole Moment in Homoleptic Ir Complexes for High Outcoupling Efficiency of Organic Light-Emitting Diodes.

The light-emitting dipole orientation (EDO) of a phosphorescent emitter is a key to improving the external quantum efficiency (EQE) of organic light-emitting diodes (OLEDs) without structural modification of the device. Here, four homoleptic Ir complexes as a phosphorescent emitter are systematically designed based on the molecular structure of tris(2-phenylpyridine)iridium(III) (Ir(ppy)3 ) to control the EDO. Trimethylsilane, methyl, 2-methylpropyl, and cyclopentylmethyl group substituted to pyridine ring of the ligand contribute to the improvement of the EDO from 76.5% for Ir(ppy)3 to 87.5%. A linear relationship between the EDO and the aspect ratio (geometric anisotropy factor) is founded, implying the importance of the effective area for the nonbonding force between host and dopant molecules. Also, it is investigated that the EDO enhancement mainly originates from the vertical alignment of the C3 axis of molecule in the substrate axis rather than the change in the direction of the transition dipole alignment in the molecular axis. The optical simulation reveals that the outcoupling efficiency of phosphorescent OLEDs adopting new dopants reaches 38.4%. The green OLEDs exhibiting 28.3% of EQE, 103.2 cd A-1 of current efficiency, and 98.2 lm W-1 of power efficiency are demonstrated, which is understood to have little electrical loss.

Highly efficient blue organic light-emitting diodes based on 2-(diphenylamino)fluoren-7-ylvinylarene derivatives that bear a tert-butyl group.

Blue fluorescent materials with a 2-(diphenylamino)fluoren-7-ylvinylarene emitting unit and tert-butyl-based blocking units were synthesized. The photophysical properties of these materials, including UV/Vis absorption, photoluminescent properties, and HOMO-LUMO energy levels, were characterized and rationalized with quantum-mechanical DFT calculations. The electroluminescent properties of these molecules were examined through the fabrication of multilayer devices with a structure of indium-tin oxide, 4,4'-bis{N-[4-(N,N-di-m-tolylamino)phenyl]-N-phenylamino}biphenyl, 4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl, and blue materials doped in 2-methyl-9,10-di(2-naphthyl)anthracene/tris(8-quinolinolato)aluminum/LiF/Al. All devices exhibit highly efficient blue electroluminescence with high external quantum efficiency (3.20-7.72 % at 20 mA cm(-2)). A deep-blue device with Commission Internationale de l'Eclairage (CIE) coordinates of (0.15, 0.11) that uses 7-[2-(3',5'-di-tert-butylbiphenyl-4-yl)vinyl]-9,9-diethyl-2-N-(3,5-di-tert-butylphenyl)-2,4-difluorobenzenamino-9H-fluorene as a dopant in the emitting layer showed a luminous efficiency and external quantum efficiency of 3.95 cd A(-1) and 4.23 % at 20 mA cm(-2), respectively. Furthermore, a highly efficient sky-blue device that uses the dopant 7-{2-[2-(3,5-di-tert-butylphenyl)-9,9'-spirobifluorene-7-yl]vinyl}-9,9-diethyl-2-N,N-diphenylamino-9H-fluorene exhibited a luminous efficiency and high quantum efficiency of 10.3 cd A(-1) and 7.7 % at 20 mA cm(-2), respectively, with CIE coordinates of (0.15, 0.20).

5-Isobutyryl-2-phenylpyridine-derived iridium complexes for red phosphorescent light-emitting diodes.

For the development of efficient red materials in organic light emitting diodes, a series of cyclometalated iridium complexes with 5-isobutyryl-2-arylpyridine-derived ligands were synthesized. Complexes 1-4 exhibited red phosphorescence with quantum yields of 0.16-0.48 in degassed CH2Cl2. An OLED device employing iridium complex 3 as a dopant exhibited the best performance with a maximum luminance of 35500 cd/m2 at 14 V and luminance and power efficiencies of 15.5 cd/A and 6.23 Im/W at 20 mA/cm2, respectively. In the device employing complex 2 as the dopant, the maximum luminance was 6300 cd/m2 at 14 V and the maximum luminance efficiency and power efficiencies were 5.23 cd/A and 3.16 Im/W at 5.2 V, respectively, with CIE coordinates of (0.66, 0.32) at 9.0 V, close to the saturated red emission.