Highly efficient red phosphorescent Ir(III) complexes for organic light- emitting diodes based on aryl(6-arylpyridin-3-yl)methanone ligands

A series of phosphorescent Ir(III) complexes 1-4 were synthesized based on aryl(6-arylpyridin-3-yl)methanone ligands, and their photophysical and electroluminescent properties were characterized. Multilayer devices with the configuration, Indium tin oxide/4,4′,4″-tris(N-(naphthalene-2-yl)-N-phenyl-amino)triphenylamine (60 nm)/4,4′-bis(N-(1-naphthyl)-N-phenylamino)biphenyl (20 nm)/Ir(III) complexes doped in N,N′-dicarbazolyl-4,4′-biphenyl (30 nm, 8%)/2,9-dimethyl-4,7-diphenyl-phenathroline (10 nm)/tris(8-hydroxyquinoline)-aluminum (20 nm)/lithium quinolate (2 nm)/ Al (100 nm), were fabricated. Among these, the device employing complex 2 as a dopant exhibited efficient red emission with a maximum luminance, luminous efficiency, power efficiency and quantum efficiency of 16200 cd/m² at 14.0 V, 12.20 cd/A at 20 mA/cm², 4.26 lm/W and 9.26% at 20 mA/cm², respectively, with Commission Internationale de l'Énclairage coordinates of (0.63, 0.37) at 12.0 V.     

Synthesis and electroluminescent properties of blue emitting materials based on arylamine-substituted diphenylvinylbiphenyl derivatives for organic light-emitting diodes

This paper reports the synthesis and electroluminescent properties of a series of blue emitting materials with arylamine and diphenylvinylbiphenyl groups for applications to efficient blue organic light-emitting diodes (OLEDs). All devices exhibited blue electroluminescence with electroluminescent properties that were quite sensitive to the structural features of the dopants in the emitting layers. In particular, the device using dopant 4 exhibited sky-blue emission with a maximum luminance, luminance efficiency, power efficiency, external quantum efficiency and CIE coordinates of 39,000 cd/m², 12.3 cd/A, 7.45 lm/W, 7.71% at 20 mA/cm² and (x = 0.17, y = 0.31) at 8 V, respectively. In addition, a blue OLED using dopant 2 with CIE coordinates (x = 0.16, y = 0.18) at 8 V exhibited a luminous efficiency, power efficiency and external quantum efficiency of 4.39 cd/A, 2.46 lm/W and 2.97% at 20 mA/cm², respectively.     

Red-phosphorescent OLEDs employing iridium (III) complexes based on 5-benzoyl-2-phenylpyridine derivatives

A series of red-phosphorescent iridium (III) complexes 1-4 based on 5-benzoyl-2-phenylpyridine derivatives was synthesized. Their photophysical and electrophosphorescent properties were investigated. Multilayered OLEDs were fabricated with a device structure ITO/4,4′,4″-tris(N-(naphtalen-2-yl)-N-phenyl-amino)triphenylamine (60 nm)/4,4′-bis(N-naphtylphenylamino)biphenyl (20 nm)/Ir(III) complexes (8%) doped in 4,4′-N,N′-dicarbazolebiphenyl (30 nm)/2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline (10 nm)/tris(8-hydroxyquinolinyl)aluminum(III) (20 nm)/Liq (2 nm)/Al (100 nm). All devices exhibited efficient red emissions. Among those, in a device containing iridium complex 1 dopant, the maximum luminance was 14200 cd/m² at 14.0 V. Also, its luminous, power, and quantum efficiency were 10.40 cd/A, 3.44 lm/W and 9.21% at 20 mA/cm², respectively. The peak wavelength of the electroluminescence was 607 nm, with CIE coordinates of (0.615, 0.383) at 12.0 V, and the device also showed a stable color chromaticity with various voltages.     

Highly efficient blue OLEDs based on diphenylaminofluorenylstyrenes end-capped with heterocyclic aromatics

In this paper, we have designed four diphenylaminofluorenylstyrene derivatives end-capped with heterocyclic aromatic groups, such as 9-phenylcabazole, 4-dibenzofuran, 2-benzoxazole, 2-quinoxaline, respectively. These materials showed blue to red fluorescence with maximum emission wavelengths of 476–611 nm, respectively, which were dependent on the structural and electronic nature of end-capping groups. To explore the electroluminescent properties of these materials, multilayer OLEDs were fabricated in the following sequence: ITO/DNTPD (40 nm)/NPB (20 nm)/2% doped in MADN (20 nm)/Alq₃ (40 nm)/Liq. (1 nm)/Al. Among those, a device exhibited a highly efficient blue emission with the maximum luminance of 14,480 cd/m² at 9 V, the luminous efficiency of 5.38 cd/A at 20 mA/cm², power efficiency of 2.77 lm/W at 20 mA/cm², and CIE_x,y coordinates of (0.147, 0.152) at 8 V, respectively.     

Single dopant white electrophosphorescent light emitting diodes using heteroleptic tris-cyclometalated Iridium(III) complexes

We report single dopant single emissive layer white organic electroluminescent (EL) device based on the heteroleptic tris-cyclometalated iridium(III) complex, Ir(dfppy)₂(pq), as the guest, where dfppy and pq are 2-(2,4-difluorophenyl) pyridine and 2-phenylquinoline, respectively, and 1,4-phenylenesis(triphenylsilane) (UGH2) as the host. The maximum luminous and power efficiencies of the device were 11.00 cd/A (J = 0.05 mA/cm²) and 5.60 lm/W (J = 0.001 mA/cm²), respectively. The CIE coordinates of the device with Ir(dfppy)₂(pq) are (0.443, 0.473) and the EL spectrum of device shows emission band at 473 and 544 nm, at the applied voltage of 12 V. The similar phosphorescent decay rate of two ligands can lead to emit luminescence in two ligands at the same time.     

t-Butyl group-substituted triphenylamine-containing orange-red fluorescent emitters for organic light-emitting diodes

Efficient orange-red fluorescent compounds, 4-(dicyanomethylene)-2-adamantyl-6-(4-(N-(4-tert-butylphenyl)-N-(3,5-di-tert-butylphenyl)amino)benzene)vinyl-4H-pyran (DCATP) and 2,6-bis[4-(N-(4-tert-butylphenyl)-N-(3,5-di-tert-butylphenyl)amino)benzene]vinyl-4-(dicyanomethylene)-4H-pyran (BDCTP) containing the tert-butylated triphenylamine in donor moieties, were synthesized and characterized. In these red emitters, bulky groups, such as t-butyl group and adamantane were introduced to increase the steric hindrance between the red emitters. In particular, an efficient orange-red device containing the emitter DCATP as a dopant showed a luminous and power efficiency of 6.87 cd/A and 2.70 lm/W, respectively, at 20 mA/cm² with the CIE coordinates of (0.48, 0.50) at 7.0 V. In addition, an efficient red organic light-emitting diode using BDCTP as a dopant exhibited a luminous and power efficiency of 2.30 cd/A and 1.31 lm/W, respectively, at 20 mA/cm² and CIE coordinates of (0.61, 0.39).     

Synthesis and electrophosphorescent properties of iridium complexes based on 2-fluorenylquinoline derivatives

A series of cyclometalated iridium complexes with 2-fluorenylquinoline derivative ligands were synthesized and their photophysical and electroluminescent properties examined using multilayered, organic light-emitting diodes fabricated with the complexes as dopant materials. In the device containing the complex 3 dopant, the maximum luminance was 20,200 cd/m² at 14 V, the luminous and power efficiencies were 14.1 cd/A and 11.0 lm/W, respectively, and the CIE coordinates were (0.65, 0.35) which were close to saturated red emission.     

Blue electroluminescent materials based on 2,7-distyrylfluorene for organic light-emitting diodes

A series of blue fluorescent 9,9-diethyl-2,7-distyryl-9H-fluorene derivatives with various capping moieties such as diphenylamino; diphenylphosphino; triphenylsilyl; phenoxy; phenylmercapto; phenylselenoxy; and triphenymethyl groups were synthesized using the Honor-Emmons reaction. The highest occupied molecular orbital-lowest unoccupied molecular orbital energy levels were characterized with a photoelectron spectrometer and rationalized with quantum mechanical density functional theory calculations. The electroluminescent properties were explored through the fabrication of multilayer devices with a structure of Indium-tin-oxide/N,N′-diphenyl-N,N′-(1-napthyl)-(1,1′-phenyl)-4,4′-diamine/2-methyl-9,10-di(2-naphthyl)anthracene:blue dopants (5-15 wt.%)/4,7-diphenyl-1,10-phenanthroline/lithium quinolate/Al. All devices, except that using NPh₂, exhibited a Commission Internationale de I'Eclairage (CIE) y value less than 0.19. The best luminous efficiency of 3.87 cd/A and external quantum efficiency of 2.65% at 20 mA/cm² were obtained in a device comprising the 4-phenylsulfanyl capped 9,9-diethyl-2,7-distyrylfluorene derivative with CIE coordinates (0.16, 0.18).     

Highly efficient blue light-emitting materials based on arylamine substituted DPVBi derivatives

A series of arylamine substituted DPVBi derivatives (1-4) were synthesized via the Horner-Wadsworth-Emmons reaction. Their electroluminescent properties were examined by fabricating a multilayer OLED device with the following structure: ITO/DNTPD (40 nm)/NPB (20 nm)/2% DPVBi derivatives (1-4) doped in MADN (20 nm)/Alq3 (40 nm)/Liq (1.0 nm)/Al. All devices showed efficient blue emission. In particular, a high efficiency blue OLED was fabricated using compound 1 as a dopant in the emitting layer. The maximum luminance, luminous efficiency, power efficiency and CIE coordinates of the blue OLED using compound 1 as a dopant were 16110 cd/m2 at 10 V, 10.1 cd/A at 20 mA/cm2, 4.37 Im/W at 20 mA/cm2, and (x = 0.197, y = 0.358) at 8 V, respectively. Moreover, a device using compound 4 as the dopant exhibited efficient deep blue emission with a luminance, luminous efficiency, power efficiency and CIE coordinates of 7005 cd/m2 at 10 V, 6.25 cd/A at 20 mA/cm2, 2.50 Im/W at 20 mA/cm2 and (x = 0.151, y = 0.143) at 8 V, respectively.     

Efficient fluorescence from 9,10-bis(m-tolylphenylamino)anthracene doped into a blue matrix in Si-based top-emitting organic light-emitting diode

We demonstrate an efficient Si-based top-emitting organic light-emitting diode using a fluorescent emitting system composed of a green dye of 9,10-bis(m-tolylphenylamino)anthracene (TPA) doped into a blue matrix of 9,9′,10,10′-tetraphenyl-2,2′-bianthracene (TPBA). The device shows green emission with a maximum luminous efficiency of 3.3 cd/A and a power efficiency of 2.3 lm/W. The maximum luminance reaches 1.3 × 10⁴ cd/m² at a driving voltage of 12 V. The excellent performances partially resulted from effective energy transfer in the emitting system of [TPBA: 2 wt.% TPA]. In addition, the emission spectra exhibit negligible variation with increasing viewing angles, indicating a weak microcavity effect because of low reflectance of Si anode.     

Modified 4-(dicyanomethylene)-2-tert-butyl-6-(1,1,7,7-tetra-methyljulolidyl-9-enyl)-4H-pyran-containing red fluorescent emitters for efficient organic light-emitting diodes

Efficient red fluorescent compounds Red 1 and Red 2 based on bulky bicyclo[2,2,2]octane groups in the pyran moiety and tert-butyl or isopropyl group in the julolidine moiety of the 4-(dicyanomethylene)-2-tert-butyl-6-(1,1,7,7-tetra-methyljulolidyl-9-enyl)-4H-pyran (DCJTB) skeleton were synthesized and characterized. As red-emitting dopants in an Alq₃ single-host emitting system, Red 1 and Red 2 exhibited improved color purity and enhanced luminous efficiency compared to DCJTB. Moreover, a device using Red 1 as a dopant in a rubrene-Alq₃ co-host emitting system exhibited improved electroluminescence performance with a luminous efficiency and power efficiency of 6.89 cd/A and 3.09 lm/W at 20 mA/cm², respectively, and CIE x,y coordinates of (x = 0.64,y = 0.36) at 7.0 V, approaching saturated red emission.     

Study on ZnGa2O4:Cr a.c. powder electroluminescent device

An a.c. powder electroluminescent (EL) device using ZnGa₂O₄:Cr³⁺ phosphor was fabricated by the screen printing method. Optical and electrical properties of the device were investigated. The fabricated device shows a red emission at 695 nm driven by the a.c. voltage. The emission is attributed to the energy transfer from hot electrons to Cr³⁺ centers via self-activated Ga-O groups. Luminance (L) versus voltage (V) matches the well-known equation of L = L₀exp(− bV ^− 1 / 2) and luminance increases proportionally with frequency due to the increase of excitation probability of host lattice or Cr³⁺ centers. The diagram of the charge density (Q) versus applied voltage (V) is based on a conventional Sawyer-Tower circuit. At 280 V and 1000 Hz, the luminance and the luminous efficiency of the fabricated powder EL device are about 1.0 cd/m² and 13 lm/W, respectively. And under the high field, the device fabricated with the oxide-based phosphor of ZnGa₂O₄:Cr³⁺ shows excellent stability in comparison with the conventional sulfide powder EL device.     

Efficient orange-red organic light-emitting diodes using 9,10-bis[4-(di-4-tert-butylphenylamino)styryl] anthracene as a fluorescent orange-red emitter

The authors have demonstrated efficient orange-red organic lighting diodes (OLEDs) using a new fluorescent orange-red material, 9,10-bis[4-(di-4-tert-buthylphenylamino)styryl]anthracene (ATBTPA). The optimized orange-red OLED using ATBTPA achieved a maximum external quantum efficiency (EQE) of 3.78%, a current efficiency (CE) of 9.47 cd/A, and Commision Internationale de L'Eclairage (CIE_x,y) coordinates of (0.51, and 0.48) at 1.61 mA/cm² in comparison with orange-red OLED using (5,6,11,12)-tetraphenyl-naphthacene (rubrene) which showed a maximum EQE of 1.65%, CE of 4.94 cd/A, and CIE_x,y coordinates of (0.50, and 0.49) at 0.61 mA/cm², respectively. The optimized orange-red device using ATBTPA showed higher efficiency of two times the orange-red device using rubrene due to the efficient Förster singlet energy transfer from MADN to ATBTPA in comparison with that from MADN to rubrene. This study clearly suggests that ATBTPA is an excellent fluorescent orange-red material for efficient WOLEDs.     

Photo/electroluminescence properties of an europium (III) complex doped in 4,4′-N,N′-dicarbazole-biphenyl matrix

The photoluminescence properties of one europium complex Eu(TFNB)₃Phen (TFNB = 4,4,4-trifluoro-1-(naphthyl)-1,3-butanedione, Phen = 1,10-phenanthroline) doped in a hole-transporting material CBP (4,4′-N,N′-dicarbazole-biphenyl) films were studied. A series of organic light-emitting devices (OLEDs) using Eu(TFNB)₃Phen as the emitter were fabricated with a multilayer structure of indium tin oxide, 250 Ω/square)/TPD (N,N′-diphenyl-N,N′-bis(3-methyllphenyl)-(1,1′-biphenyl)-4,4′-diamine, 50 nm)/Eu(TFNB)₃phen (x): CBP (4,4′-N,N′-dicarbazole-biphenyl, 45 nm)/BCP (2,9-dimethyl-4,7-diphenyl-l,10 phenanthroline, 20 nm)/AlQ (tris(8-hydroxy-quinoline) aluminium, 30 nm)/LiF (1 nm)/Al (100 nm), where x is the weight percentage of Eu(TFNB)₃phen doped in the CBP matrix (1-6%). A red emission at 612 nm with a half bandwidth of 3 nm, characteristic of Eu(III) ion, was observed with all devices. The device with a 3% dopant concentration shows the maximum luminance up to 1169 cd/m² (18 V) and the device with a 5% dopant concentration exhibits a current efficiency of 4.46 cd/A and power efficiency of 2.03 lm/W. The mechanism of the electroluminescence was also discussed.     

Highly efficient blue light-emitting diodes based on diarylanthracene/triphenylsilane compounds

New host materials have been designed and synthesized, (4-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)triphenylsilane (ANPTPS) and (9,9-dimethyl-7-(10-(naphthalen-2-yl)anthracen-9-yl)-9H-fluoren-2-yl)triphenylsilane (ANFTPS), and photophysical characteristics investigated to determine suitability as candidates for blue light-emitting materials. To explore the electroluminescent properties, multilayered OLEDs were fabricated with the device structure of ITO/NPB/Host (ANPTPS and ANFTPS): 8% Dopant (PFVtPh and PCVtPh)/Bphen/Liq/Al. By using a host (ANPTPS) and a dopant (PFVtPh) as the emitting layer, high-efficiency blue OLEDs were fabricated with a maximum luminance of 3991 cd/cm2 at 8.0 V, a luminous efficiency of 5.99 cd/A at 20 mA/cm2, a power efficiency of 3.11 lm/W at 20 mA/cm2, an external quantum efficiency of 4.13% at 20 mA/cm2, and CIEx, y coordinates of (x = 0.15, y = 0.18) at 8.0 V.     

A new yellow fluorescent dopant for high-efficiency organic light-emitting devices

We describe the design and synthesis of a sterically hindered yellow dopant, tetra(t-butyl)rubrene (TBRb) which, when doped in either 1,4-bis[N-(1-naphthyl)-N′-phenylamino]-biphenyl or aluminum tris(8-hydroxyquinoline) (Alq₃) as emitter, shows nearly 25% increase in luminance efficiency over that of the state-of-the-art rubrene (Rb) device without significantly effecting its corresponding color. At 5% doping in Alq₃ and 20 mA/cm² current drive condition, the electroluminescence efficiency of TBRb reaches 8.5 cd/A and 2.8 lm/W with a yellow color of Commission Internationale de l'Eclairage chromaticity coordinates (CIE_x,y) = [0.52, 0.48], which is among the best ever reported for yellow electrofluorescence in organic light-emitting devices.     

Electroluminescence from single-layer thin-film devices based on three binuclear Ru(II) complexes with different length of flexible bridges

The spectroscopic, electrochemical and electroluminescent properties of three binuclear Ru(II) complexes with different length of flexible bridges were investigated. The single-layer electroluminescent devices with configuration of indium-tin oxide/Ru complex (~ 100 nm)/Ga:In were found to give a turn-on voltages as low as 2.3 V, a maximum luminance up to 310 cd/m² at a bias voltage of 5.8 V, and low delay times less than 2 s.     

Efficient triplet exciton confinement of white organic light-emitting diodes using a heavily doped phosphorescent blue emitter

We demonstrated efficient white electrophosphorescence with a heavily doped phosphorescent blue emitter and a triplet exciton blocking layer (TEBL) inserted between the hole transporting layer (HTL) and the emitting layer (EML). We fabricated white organic light-emitting diodes (WOLEDs) (devices A, B, C, and D) using a phosphorescent red emitter; bis(2-phenylquinolinato)-acetylacetonate iridium III (Ir(pq)₂acac) doped in the host material; N,N′-dicarbazolyl-3,5-benzene (mCP) as the red EML and the phosphorescent blue emitter; bis(3,5-Difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl) iridium III (FIrpic) doped in the host material; p-bis(triphenylsilyly)benzene (UGH2) as the blue EML. The properties of device B, which demonstrate a maximum luminous efficiency and external quantum efficiency of 26.83 cd/A and 14.0%, respectively, were found to be superior to the other WOLED devices. It also showed white emission with CIE_x,y coordinates of (x = 0.35, y = 0.35) at 8 V. Device D, which has a layer of P-type 4,4′,4″-tri(N-carbazolyl)triphenylamine (TCTA) material between the HTL and TEBL, was compared with device A to determine the 430 nm emission peak.     

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.     

Modified DCM-type materials for red fluorescent organic light-emitting diodes

A series of red emitters 1-3 based on modified DCM were synthesized and their electroluminescent properties were investigated. A device employing red emitter 2 as a dopant exhibited efficient red emission with maximum luminous efficiency of 1.87 cd/A, maximum power efficiency of 0.78 lm/W, maximum external quantum efficiency of 1.52%, and CIE coordinates of (0.65, 0.35) at 7.0 V.