Highly efficient iridium(III) complexes with diphenylquinoline ligands for organic light-emitting diodes: Synthesis and effect of fluorinated substitutes on electrochemistry, photophysics and electroluminescence

A series of novel cyclometalated iridium(III) complexes bearing 2,4-diphenylquinoline ligands with fluorinated substituent were prepared and characterized by elemental analysis, NMR and mass spectroscopy. The cyclic voltammetry, absorption, emission and electroluminescent properties of these complexes were systematically investigated. Electrochemical studies showed that the oxidation of the fluorinated complexes occurred at more positive potentials (in the range 0.57-0.69 V) than the unfluorinated complex 1 (0.42 V). In view of the energy level, the lowering of the LUMO by fluorination is significantly less than that of the HOMO. The weak and low energies absorption bands in the range of 300-600 nm are well resolved, likely associated with MLCT and (3)pi-pi* transitions. These complexes show strong orange red emission both in the solution and solid state. The emission maxima of the fluorinated complexes showed blue shift by 9, 24 and 15 nm for 2, 3 and 4, respectively, with respect to the unfluorinated analogous 1. Multilayered organic light-emitting diodes (OLEDs) were fabricated by using the complexes as dopant materials. Significantly higher performance and lower turn-on voltage were achieved using the fluorinated complexes as the emitter than that using the unfluorinated counterpart 1 under the same doping level.

Effect of dye-doped concentration on the charge carrier recombination in molecularly doped organic light-emitting devices

The effect of the concentration of 4-(dicyanomethylene)-2-t-butyl-6(1,1,7,7-tetramethyljulolidyl- 9-enyl)-4H-pyran(DCJTB) as dopant in tris(8-hydroxyquinoline) aluminium (Alq(3)) on the charge carrier recombination was studied by transient electroluminescence (EL). The electron-hole recombination coefficient (gamma) was determined from the long-time component of the temporal decay of the EL intensity after a rectangular voltage pulse was turned off. It was found that the coefficient monotonically decreased with an increase in the DCJTB-doping concentration. The monotonic decrease is attributed to concentration quenching on the excitons and coincided well with the reduction of the EL efficiency.

High-efficiency spin-coated organic light-emitting diodes based on a europium complex

An organic light-emitting diode fabricated by doping a europium, complex tris(dibiphenoylmethane)-mono (phenanthroline)-europium (Eu(DBPM)(3) (Phen)) into polymer poly(2-methoxy-5-(2-ethyl-hexyloxy)-1,4-phenylene) and poly(N-carbazole) was realized by spin coating. Comparison with other europium complexes, due to the existence of a larger spectral overlap between Eu(DBPM)(3)(Phen) and poly(2-methoxy-5-(2-ethyl-hexyloxy)-1,4phenylene), a high efficiency red emission was achieved. The device showed a turn-on voltage of 5.2 V The maximum efficiency reached 0.47 cd/A at luminance of 50 cd/m(2). The maximum luminance can reach 150 cd/m(2) at 95 mA/cm(2). To the best of our knowledge, this is one of the best results based on europium complexes by spin-casting method.

Microcavity effects on emissive color and electroluminescent performance in organic light-emitting diodes

Microcavity organic light-emitting diodes having a top metal mirror and a bottom dielectric mirror, which was distributed Bragg reflectors (DBR) fabricated by using TiO2-SiO2 alternative dielectric multilayer with a central stop-band and two sub-stop-bands, were fabricated. In the devices, the active layers consisted of a hole-transporting layer N,N'-di(naphthalene-1-yl)-N,N'-diphenylbenzidine (NPB) and an electron- transporting/emitting layer tris(8-hydroxy-quinoline) aluminum (Alq(3)). The relationship of the electroluminescent (EL) spectrum and efficiency with the thickness of the active layer and metal layer was studied. It was found that the EL emissive color did not strongly depend on the thickness of the organic layer and metal layer, which was attributed to the excellent photon confinement role of the narrow stop-band of the used dielectric mirror. Thus, high efficiency microcavity organic light-emitting diodes were achieved, and the peak wavelength and color purity were not obviously changed, via optimizing the thickness of organic layer and metal electrode.

Highly efficient red electroluminescence from stacked organic light-emitting devices based on a europium complex

Stacked organic light-emitting devices (OLEDs) based on a europium complex Eu(TTA)(3) (Tmphen) (TTA = thenoyltrifluoroacetone,Tmphen = 3,4,7,8-tetramethyl-1,10-phenanthroline) were fabricated. In this stacked OLEDs, Li:BCP/V2O5 was used the intermediate charge generation layer sandwiched between two identical emissive units consisting of TPD/CBP:DCJTB:Eu(TTA)(3)(Tmphen)/BCP. As expected, the brightness and electroluminescent (EL) current efficiency were approximately enhanced by double times that of conventional single-unit devices. The stacked OLEDs showed the maximum luminance up to 3000 cd/m(2) at a current density of 190 mA/cm(2) and a current efficiency of 14.5 cd/A at a current density of 0.08 mA/cm(2). At the brightness of 100 cd/m(2), the current efficiency reached 10 cd/A at a current density of 1.6 mA/cm2.

High efficiency red organic light-emitting diodes based on microcavity structure

We demonstrate high efficiency red organic light-emitting diodes (OLEDs) based on a planar microcavity comprised of a dielectric mirror and a metal Mirror. The microcavity devices emitted red light at a peak wavelength of 610 nm with a full width at half maximum (FWHM) of 25 nm in the forward direction, and an enhancement of about 1.3 factor in electroluminescent (EL) efficiency has been experimentally achieved with respect to the conventional noncavity devices. For microcavity devices with the structure of distributed Bragg reflectors (DBR)/indium-tin-oxide(ITO)/V2O5/N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine(NPB)/4-(dicy-anome-thylene)-2-t-butyl-6(1,1,7,7-tetrame-thyljulolidyl-9-enyl)-4H-pyran(DCJTB):tris(8-hydroxyquinoline) aluminium (Alq(3))/Alq(3)/LiF/Al, the maximum brightness arrived at 37000 cd/m(2) at a current density of 460.0 mA/cm(2), and the current efficiency and power efficiency reach 13.7 cd/A at a current density of 0.23 mA/cm(2) and 13.3 lm/W respectively.

Improved performance and stability by an Al/Ni bilayer cathode in organic light-emitting diodes

Al/Ni bilayer cathode was used to improve the electroluminescent (EL) efficiency and stability in N,N'-bis(1-naphthyl)-N,N'-diphenyl-1,1' biphenyl 4,4'-dimaine (NPB)/tris-(8-hydroxyquinoline) aluminum (Alq(3))-based organic light-emitting diodes. The device with LiF/Al/Ni cathode achieved a maximum power efficiency of 2.8 lm/W at current density of 1.2 mA/cm(2), which is 1.4 times the efficiency of device with the state-of-the-art LiF/Al cathode. Importantly, the device stability was significantly enhanced due to the utilization of LiF/Al/Ni cathode. The lifetime at 30% decay in luminance for LiF/Al/Ni cathode was extrapolated to 400 It at an initial luminance of 100 cd/m(2), which is 10 times better than the LiF/Al cathode.

NaCl/Ca/Al as an efficient cathode in organic light-emitting devices

An efficient cathode NaCl/Ca/Al used to improve the performance of organic light-emitting devices (OLEDs) was reported. Standard NM-bis(1-naphthyl)-NAP-diphenyl-1,1' biphenyl 4,4'-dimaine (NPB)/tris-(8-hydroxyquinoline) aluminum (Alq(3)) devices with NaCl/Ca/Al cathode showed dramatically enhanced electroluminescent (EL) efficiency. A power efficiency of 4.6 lm/W was obtained for OLEDs with 2 nm of NaCl and 10 nm of Ca, which is much higher than 2.0 lm/W, 3.1 lm/W, 2.1 lm/ W and 3.6 lm/W in devices using, respectively, the LiF (1 nm)/Al, LiF (1 nm)/Ca (10 nm)/Al, Ca (10 nm)/Al and NaCl (2 nm)/ Al cathodes. The investigation of the electron injection in electron-only devices indicates that the utilization of the NaCl/Ca/Al cathode substantially enhances the electron injection current, which in case of OLEDs leads to the improvement of the brightness and efficiency.

Organic white-light-emitting devices based on a multimode resonant microcavity

Organic white-light-emitting devices ( OLEDs) based on a multimode resonant microcavity defined by a pair of dielectric mirrors and metal mirrors were presented. By selective effects of the quarter-wave dielectric stack mirror on mode, white light emission containing three individual narrow peaks of red, green and blue was achieved, and showed weak dependence on the viewing angle. The Commission Internationale De L'Eclairage ( CIE) chromaticity coordinates changed from ( 0.29, 0.37) at 0 degrees to ( 0.31, 0.33) at 40 degrees. Furthermore, the brightness and electroluminescence efficiency of the microcavity OLEDs were enhanced compared with noncavity OLEDs. The maximum brightness reached 1940 cd m(-2) at a current density of 200 mA cm(-2), and the maximum current efficiency and power efficiency are 1.6 cd A(-1) at a current density of 12 mA cm(-2) and 0.41 1m W-1 at a current density of 1.6 mA cm(-2), which are over 1.6 times higher than that of a noncavity OLED.

Reduced ambient reflection of organic light-emitting diodes by utilizing multilayer low-reflection cathodes

Ambient reflection of organic light-emitting diodes (OLEDs) is reduced by utilizing a multilayer low-reflection cathode. The low-reflection cathode structure consists of a semitransparent cathode layer, a transparent spacing layer and a high reflective layer. Metals with different optical properties, including silver (Ag) and samarium (Sm), are used as the semitransparent cathode layer, tris(8-quinolinolato) aluminium (Alq(3)) and aluminium (Al) are used as the spacing layer and high reflective layer, respectively. The incident ambient light could be reduced by the cathode structure via destructive optical interference. It is found that the Ag/Alq(3)/Al cathode shows a strong wavelength-dependent reflection. However, the Sm/Alq(3)/Al cathode demonstrates a low reflection in the whole visible range, and the resulting OLED shows a reduced luminous reflectance of 2.7% as compared to 81% for a control device with LiF/Al cathode. A further reduction to 0.9% is realized by replacing a multilayer of Alq(3)/Sm/Alq(3) for the single layer of Alq(3).

High efficiency white organic light-emitting diodes based on double recombination zones

A multilayer white organic light-emitting diode (OLED) with high efficiency was present. The luminescent layer was composed of a red dye 4-(dicyanomethylene)-2-t-butyle-6-(1,1,7,7-tetra-methyljulolidyl-9-enyl)-4H-pyran (DCJTB) doped into NN-bis-(1-naphthyl)-N,N-diphenyl-1,1-biphenyl-4-4-diamine (NPB) layer and a blue-emitting 9,10-bis-(beta-naphthyl)-anthrene (DNA) layer. Red and blue emission, respectively, from DCJTB:NPB and DNA can be obtained by effectively controlling the thicknesses of DCJTB:NPB and DNA layers, thus a stable white light emission was achieved. The device turned on at 3.5 V, and the maximum luminance reached 16000 cd/m(2) at 21 V. The maximum current efficiency and power efficiency were 13.6 cd/A and 5.5 lm/W, respectively.

New fluorescent dipolar pyrazine derivatives for non-doped red organic light-emitting diodes

Dipolar fluorescent compounds containing electron-accepting pyrazine-2,3-dicarbonitrile and electron-donating arylamine moiety have been designed and synthesized. The optical and electrochemical properties of these compounds can be adjusted by changing pi-bridge length and the donor (D) strength. Organic light-emitting devices based on these compounds are fabricated. Saturated red emission of (0.67, 0.33) and the external quantum efficiency as high as 1.41% have been demonstrated for one of these compounds.

Dependence of performance of organic light-emitting devices on sheet resistance of indium-tin-oxide anodes

The dependence of the performance of organic light-emitting devices(OLEDs) on the sheet resistance of indium-tin-oxide(ITO) anodes was investigated by measuring the steady state current density brightness voltage characteristics and the electroluminescent spectra. The device with a higher sheet resistance anode shows a lower current density, a lower brightness level, and a higher operation voltage. The electroluminescence(EL) efficiencies of the devices with the same structure but different ITO anodes show more complicated differences. Furthermore, the shift of the light-emitting zone toward the anode was found when an anode with a higher sheet resistance was used. These performance differences are discussed and attributed to the reduction of hole injection and the increase in voltage drop over ITO anode with the increase in sheet resistance.

A wide-bandgap semiconducting polymer for ultraviolet and blue light emitting diodes

A novel wide-bandgap conjugated polymer (PDHFSCHD) consisting of alternating dihexylfluorene and rigidly twisted biphenyl units has been synthesized. The new fluorene-based copolymer composed of rigid twisting segments in the main-chain exhibits an optical bandgap of as high as 3.26 eV, and a highly efficient ultraviolet emission with peaks at 368 nm and 386 nm. An electroluminescence device from PDHFSCHD neat film as an active layer shows UV emission which peaks at 395 nm with a turn on voltage below 8 V By optimizing the device conditions, a peak EL quantum efficiency of 0.054% and brightness of 10 cd.m(-2) was obtained. Furthermore, blending a poly(dihexylfluorene) in the PDHFSCHD host gave pure blue emission peaking at 417 nm, and 440 nm without long wavelength emission from aggregated species. Efficient energy transfer from PDHFSCHD to PDHF was demonstrated in these blended systems. Depressed chain-aggregation of PDHF in the PDHFSCHD host can correspond to pure blue emission behaviors.

Novel PPV-based light-emitting copolymers containing triazole moiety

Two new light-emitting PPV-based copolymers bearing electron-withdrawing triazole unit in the main chain have been synthesized by Wittig reaction between triazole diphosphonium salt and the corresponding dialdehyde monomers, respectively. Their optical and physical properties are characterized by UV-vis, photoluminescence (PL), TGA and DSC. The resulting copolymers are highly soluble in common organic solvents and have high Tg and Td values. They show blue-greenish fluorescence in solution (lambda(max) 502 and 508 nm) and green fluorescence in the solid state (lambda(max) 520 and 526 nm), respectively.