High efficiency green phosphorescent organic light emitting device with (TCTA/TCTA0.5TPBi0.5/TPBi): Ir(ppy)3 emission layer

A new high efficiency green light emitting phosphorescent device with an emission layer consisting of {4,4',4'-tris(N-carbazolyl)-triphenylamine[TCTA]/TCTA_0.5TPBi_0.5/1,3,5-tris(N-phenylbenzimiazole-2-yl)benzene[TPBi]}:tris(2-phenylpyridine)iridium(III)[Ir(ppy)₃] was fabricated and its electroluminescence characteristics were evaluated in comparison with those of devices with emission layers made of (TCTA_0.5TPBi_0.5):Ir(ppy)₃ and (TCTA/ TPBi):Ir(ppy)₃.The device with the emission layer consisting of (TCTA/TCTA_0.5TPBi_0.5/TPBi):Ir(ppy)₃ showed a luminance of 11,000 cd/m² at an applied voltage of 8 V and maximum current efficiency of 63 cd/A under a luminance of 500 cd/m². The peak wavelength in the electroluminescent spectral and color coordinate on the Commission Internationale de I'Eclairage(CIE) chart were 513 nm and (0.31, 0.62) in this device, respectively. Under a luminance of 10000 cd/m², the current efficiency of this device was 55 cd/A, which is 1.4 and 1.1 times better than those of the devices with the emission layers made of (TCTA_0.5TPBi_0.5):Ir(ppy)₃ and (TCTA/TPBi):Ir(ppy)₃, respectively.     

Experimental study of the organic light emitting diode with a p-type silicon anode

We have fabricated and studied an organic light emitting diode (OLED) with a p-type silicon anode and a SiO₂ buffer layer between the anode and the organic layers which emits light from a semitransparent top Yb/Au cathode. The luminance of the OLED is up to 5600 cd/m² at 17 V and 1800 mA/cm², the current efficiency is 0.31 cd/A. Both its luminance and current efficiency are much higher than those of the OLEDs with silicon as the anodes reported previously. The enhancement of the luminance and efficiency can be attributed to an improved balance between the hole- and electron-injection through two efficient ways: 1) restraining the hole-injection by inserting an ultra-thin SiO₂ buffer layer between the Si anode and the organic layers; and 2) enhancing the electron-injection by using a low work function, low optical reflectance and absorption semitransparent Yb/Au cathode.     

Properties of flexible phosphorescence polymer light emitting diodes coated on polyethylenenaphthalate plastic substrates

Flexible phosphorescence polymer light emitting diodes (PhPLEDs) with PEN/ITO/PEDOT:PSS/ PVK:Ir(ppy)3/TPBI/LiF/Al structure were fabricated to investigate the effects of Ir(ppy)3 doping concentrations on the optical and electrical properties of the devices. PVK and Ir(ppy)3 conjugated polymers as host and guest materials in the emission layer were spun coated at various concentrations of Ir(ppy)3 ranging from 2.0 to 8.0 vol%. As the concentration of Ir(ppy)3 increased from 2.0 to 6.0 vol%, the electrical and optical properties of the flexible PhPLEDs were improved clearly. Maximum luminance and current density were obtained for a PhPLED with an Ir(ppy)3 concentration of 6.0 vol%, with 6815 cd/m2 and 393 mA/cm2 at 9 V. The current efficiency tends to increase with the Ir(ppy)3 concentration, because of the formation of the excitons required to emit light.     

Efficient red electrophosphorescent organic light-emitting diodes based on the new sensitized heteroleptic tris-cyclometalated Ir(III) complexes

Organic light-emitting device (OLED) was fabricated using the novel red phosphorescent heteroleptic tris-cyclometalated iridium complex, bis(2-phenylpyridine)iridium(III)[2(5′-methylphenyl)-4-diphenylquinoline] [Ir(ppy)₂(dpq-5CH₃)], based on 2-phenylpyridine (ppy) and 2(5′-methylphenyl)-4-diphenylquinoline (dpq-5CH₃) ligand. Generally, the ppy ligand in heteroleptic iridium complexes plays an important role as “sensitizer” in the efficient energy transfer from the host (CBP; 4,4,N,N′-dicarbazolebiphenyl) to the luminescent ligand (dpq-5CH₃). We demonstrated that high efficiency through the “sensitizer” can be obtained, when the T₁ of the emitting ligand is close to T₁ of the sensitizing ligand. The device containing Ir(ppy)₂(dpq-5CH₃) produced red light emission of 614 nm with maximum luminescence efficiency and power efficiency of 8.29 cd/A (at 0.09 mA/cm²) and 5.79 lm/W (at 0.09 mA/cm²), respectively.     

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 blue-green organic light-emitting diodes based on heteroleptic tris-cyclometalated iridium(III) complexes

The blue-green organic light-emitting diodes based on heteroleptic tris-cyclometalated iridium(III) complexes containing the F₂-ppy (2,4-difluorophenylpyridine) and ppy (2-phenylpyridine) ligands were fabricated. Ir(ppy)₃ has been known to have a high phosphorescence efficiency in electroluminescence owing to its strong metal-to-ligand-charge transfer (MLCT) excited state, whereas the luminous efficiency of Ir(F₂-ppy)₃ was found to be low due to weak MLCT. Herein, we report two heteroleptic phosphorescent blue-green emitters, Ir(ppy)₂(F₂-ppy) and Ir(ppy)(F₂-ppy)₂, that exhibit emission peaks at 502 nm and 495 nm, respectively. The maximum luminous efficiencies of the devices with Ir(ppy)₂(F₂-ppy) and Ir(ppy)(F₂-ppy)₂ were 8.93 cd/A and 13.80 cd/A, respectively. The quantum efficiency of the device containing Ir(ppy)(F₂-ppy)₂ was 3.63% at J = 10 mA/cm².     

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.     

Solution-processed high-efficiency organic phosphorescent devices utilizing a blue Ir(III) complex

We report high-efficiency blue phosphorescence organic light-emitting devices by solution process utilizing a blue Ir(III) complex [(F2ppy)2Ir(ph-imz)CN] (F2ppy = 2',6' -difluoro-2-phenyl pyridine and ph-imz = N-phenyl imidazole) blended with the host mCP (N, N'-dicarbazolyl-3,5-benzene), and the inert polymers polystyrene (PS) and polymethylmethacrylate (PMMA). The effects of the dopant confinement in the PS and PMMA matrix on the device performance are studied by field emission transmission electron microscopy (FE-TEM) and atomic force microscopy (AFM). The complex shows photoluminescence peaked at 458 nm with CIE color coordinates (0.14, 0.21) in solution and (0.14, 0.18) in doped PMMA film. The PS based device showed better device performance than the PMMA based device with a maximum luminous efficiency of (etaL) 5.11 cd/A with CIE color coordinates (0.17, 0.29) (at 10 mA/cm2) and a maximum luminance of 9765 cd/m2.     

Electric field tunable light emitting diodes containing europium β-diketonates with [2.2]paracyclophane moiety

The synthesis and electroluminescent (EL) properties of two europium complexes with unsymmetrical β-diketonates and 1,10-phenanthroline are reported. The molecules are substituted by functional groups with different donor–acceptor properties and contain [2.2]paracyclophane moiety. They were used to fabricate the organic light emitting diodes (OLEDs). A large emission wavelength tunability by the applied electric field is observed for OLED containing europium β-diketonate substituted by phenyl group, with the maximum of luminance of 8 cd/m². Such tunability disappears for OLED based on europium β-diketonate substituted by CH₃ group, for which the luminance decreases to ca 2.5 cd/m². Also in that case an emission band in UV disappears. The OLED stability is lower in the latter case too, showing the importance of the substitution on the OLED operation. It shows also a high potential for the electroluminescent properties control and improvement of these Eu based macromolecules through a simple β-diketonate ligand chemical structure modification.     

Red organic light emitting devices with reduced efficiency roll-off behavior by using hybrid fluorescent/phosphorescent emission structure

Organic light emitting device (OLED) with a fluorescence-interlayer-phosphorescence emissive structure (FIP EML) is proposed to solve efficiency roll-off issue effectively. By doping fluorescent emitter of 4-(dicyanomethylene)-2-t-butyl-6-(1,1,7,7-tetramethyljulolidyl-9-enyl)-4H-pyran (DCJTB) and phosphorescent emitter of tris(1-phenylisoquinolinolato-C2,N)iridium(III) (Ir(piq)₃) into the different regions of emission zone to form FIP EML in red OLED, an improvement of more than 20% in luminance efficiency roll-off compared with that of typical phosphorescent OLED with single EML in 10-500 mA/cm² range has been obtained. Detailed mechanisms have been studied. Such improvement should be attributed to the distinct roles of the two emitters, where DCJTB mainly used to influence the carrier transport leading to an improved balance of charge carriers while Ir(piq)₃ functions as the radiative decay sites for most generated excitons. Meanwhile, with the help of the formation of FIP EML, the redistribution of excitons in recombination zone, the suppression of non-radiative exciton quenching processes and the elimination of energy transfer loss also contribute to the enhancement of efficiency roll-off. The method proposed here may provide a route to develop efficient OLED for high luminance applications.     

High performance inkjet printed phosphorescent organic light emitting diodes based on small molecules commonly used in vacuum processes

High efficiency phosphorescent organic light emitting diodes (OLEDs) are realized by inkjet printing based on small molecules commonly used in vacuum processes in spite of the limitation of the limited solubility. The OLEDs used the inkjet printed 5 wt.% tris(2-phenylpyridine)iridium(III) (Ir(ppy)₃) doped in 4,4′-Bis(carbazol-9-yl)biphenyl (CBP) as the light emitting layer on various small molecule based hole transporting layers, which are widely used in the fabrication of OLEDs by vacuum processes. The OLEDs resulted in the high power and the external quantum efficiencies of 29.9 lm/W and 11.7%, respectively, by inkjet printing the CBP:Ir(ppy)₃ on a 40 nm thick 4,4′,4″-tris(carbazol-9-yl)triphenylamine layer. The performance was very close to a vacuum deposited device with a similar structure.     

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.     

Iridium-based light-emitting electrochemical cells containing ionic liquids in the luminous layer

To fabricate transition metal complex-based LECs (light-emitting electrochemical cells), ([Ir(ppy)₂(5,6-dime-1,10-phenthroline)]PF₆ was synthesized and used as a luminous material and ILs (ionic liquids) were incorporated into a luminous layer, in which two types of ionic liquid were used; 1-butyl-3-methylimidazolium hexafluorophosphate (BMIMPF₆) and 1-butyl-3-methylimidazolium tetrafluoroborate (BMIMBF₄). ILs were added to a [Ir(ppy)₂(5,6-dime-1,10-phenthroline)]PF₆ luminous layer to improve ionic conductivity and light intensity. Both ILs significantly increased the current density and luminance. Due to the small molecule of BF₄^?, turn-on time was reduced and ionic conductivity was increased. However, the device stability was sacrificed. High current efficiency of 34.5 cd/A was investigated at 7 V of BMIMPF₆-doped luminous layer. The LECs based on [Ir(ppy)₂(5,6-dime-1,10-phenthroline)]PF₆ gave yellow emission color when ILs were added into light-emitting layer, and no significant change of color has been found in this study.     

Triplet to singlet transition induced low efficiency roll-off in green phosphorescent organic light-emitting diodes

Phosphorescent organic light-emitting diodes (PHOLEDs) with an emitting layer of 4,4′-N,N′-dicarbazole-biphenyl codoped with phosphor fac-tri(phenylpyridine)iridium(III) [Ir(ppy)₃] and fluorophore N,N’-dimethy-quinacridone (DMQA) are investigated. Predominant emission from DMQA due to the efficient energy transfer from Ir(ppy)₃ to DMQA is observed. Such an energy transfer results in the transition of Ir(ppy)₃ triplet to DMQA singlet, which reduces the Ir(ppy)₃ exciton lifetime and hence suppresses the triplet-triplet annihilation and triplet-polaron annihilation of Ir(ppy)₃ excitons, leading to dramatical reduction of the efficiency roll-off of the PHOLEDs. This transition of triplet to singlet strategy provides a method to improve the efficiency roll-off of the PHOLEDs.     

High-efficiency white organic light-emitting devices with a non-doped yellow phosphorescent emissive layer

Highly efficient phosphorescent white organic light-emitting devices (PHWOLEDs) with a simple structure of ITO/TAPC (40 nm)/mCP:FIrpic (20 nm, x wt.%)/bis[2-(4-tertbutylphenyl)benzothiazolato-N,C²′] iridium (acetylacetonate) (tbt)₂Ir(acac) (y nm)/Bphen (30 nm)/Mg:Ag (200 nm) have been developed, by inserting a thin layer of non-doped yellow phosphorescent (tbt)₂Ir(acac) between doped blue emitting layer (EML) and electron transporting layer. By changing the doping concentration of the blue EML and the thickness of the non-doped yellow EML, a PHWOLED comprised of higher blue doping concentration and thinner yellow EML achieves a high current efficiency of 31.7 cd/A and Commission Internationale de l'Eclairage coordinates of (0.33, 0.41) at a luminance of 3000 cd/m² could be observed.     

Organic light emitting diodes based on dipyridamole drug

The dipyridamole drug [DIP: 2,6-bis(diethanolamino)-4,8-dipiperidinopyrimido(5,4-d)pyrimidine] is widely used in treatment of coronary heart disease for its antiplatelet and vasodilating activities, and its high intensity photoluminescence (PL) has been widely reported. In this work, the fabrication and the characterization of a new OLED using the DIP molecule as an emitting layer is reported. The devices were assembled using a heterojunction between three organic molecular materials: the N,N′-bis(naphthalen-1-yl)-N,N′-bis(phenyl)benzidine (NPB) or the 1-(3-methylphenyl)-1,2,3,4-tetrahydroquinoline-6-carboxyaldehyde-1,1′-diphenylhydrazone (MTCD) as hole-transporting layer, the DIP layer as an emitting layer and the tris(8-hydroxyquinoline aluminum) (Alq₃) as the electron transporting layer. All the organic layers were sequentially deposited in a high vacuum by thermal evaporation onto indium tin oxide substrates and without breaking vacuum. Continuous electroluminescence emission was obtained in all configurations upon varying the applied bias voltage from 4 to 30 V, the observed wide emission band was centered at 493 nm. The luminance of the devices was about 1500 (cd)/m² with 4.5 cd/A of efficiency for the best device. The charge transport behavior in the OLED is also discussed as a function of different carrier injection levels.     

Pyridine/isoquinoline-carbazole containing bipolar host materials for green phosphorescent organic light-emitting diodes

We demonstrated the electroluminescent properties of bipolar host materials such as 9-(3-(6-methylpyridin-2-yl)phenyl)-9H-carbazole (Czpmpy), 9-(6-phenylpyridin-2-yl)-9H-carbazole (Czppy), and 9-(3-(isoquinolin-1-yl)phenyl)-9H-carbazole (Czpiq). Particularly, by using host (Czpiq) and dopant (bis[2-(1,1',2',1"-terphen-3-yl)pyridinato-C,N]iridium(III) (tphpy),2Ir(acac)) as the emitting layer, a green phosphorescent OLED was fabricated, showing a maximum luminance of 12780 cd/m2 at 10 V, maximum luminous efficiency of 45.0 cd/A, power efficiency of 47.1 Im/W, maximum external quantum efficiency of 12.3%, and CIE x, y coordinates of (0.34, 0.58) at 8 V.     

Highly efficient phosphorescent organic light emitting diodes based on iridium(III) complex with bulky substituent spacers

We developed highly efficient phosphorescent organic light emitting diodes (PHOLEDs) using iridium(III) complex, fac-tris[4-methyl-2-2(4'-trimethylsilylphenyl)pyridine] [Ir(msippy)3]. PHOLEDs based on Ir(msippy)3 complex exhibit the yellowish-green emission with CIE color coordinates of (0.31,0.64). These device performances were compared with those of the green emitting Ir(ppy)3-based devices. The higher external quantum efficiency (EQE) of 25.6% and the current efficiency of 84.4 cd/A were achieved for Ir(msippy)3-based device. The results show that the complete energy and/or charge transfer from the host to Ir(msippy)3 dopant in the emitting layer (EML) of the device resulted in the higher device efficiencies compared with those of Ir(ppy)3-based devices.     

Heteroleptic tris-cyclometalated iridium(III) complexes with phenylpridine and diphenylquinoline derivative ligands

The synthesis and photophysical study of efficient phosphorescent heteroleptic tris-cyclometalated iridium(III) complexes having two different (C^N) ligands are reported. In order to improve the luminescence efficiency by avoiding triplet-triplet (T-T) annihilation, new heteroleptic tris-cyclometalated iridium complexes, Ir(ppy)₂(dpq), Ir(ppy)₂(dpq-3-F) and Ir(ppy)₂(dpq-CF₃), are designed and prepared where ppy, dpq, dpq-3-F and dpq-CF₃ represent 2-phenylpyridine, 2,4-diphenylquinoline, 2-(3-fluorophenyl)-4-phenylquinoline, and 4-phenyl-2-(4-(trifluoromethyl)phenyl)quinoline, respectively. Ppy ligands and dpq derivatives can act as a source of energy supply. When new heteroleptic tris-cyclometalated iridium complex, Ir(ppy)₂(dpq-3-F) is placed in the lowest excited state, the excitation energy is neither quenched nor deactivated but quickly intermolecularly transferred from two ppy ligands to one luminescent dpq-3-F ligand. Such transfer can occur because the triplet energy level of Ir(ppy)₃ is higher than that of Ir(dpq-3-F)₃ and because Ir(dpq-3-F)₃ was known to have a shorter lifetime than that of Ir(ppy)₃. As a result, Ir(ppy)₂(dpq-3-F) shows strong emission band at 620 nm from dpq-3-F ligand in the end. Thus it allows more reddish luminescent color and improves the luminescence by the decrease of quenching or energy deactivation by decreasing the number of the luminescent ligand. To analyze luminescent mechanism, we calculated these complexes theoretically by using computational method.     

Solution-processed small molecule thin films and their light-emitting devices

Thin films of N,N′-bis-(3-Naphthyl)-N,N′-biphenyl-(1,1′-biphenyl)-4,4′-diamine (NPB), tris-(8-hydroxyquinoline)-aluminum (Alq₃) and their blends prepared by spin-coating process were investigated. Experimental results revealed that the NPB films prepared by spin-coating process have smoother surface than that of Alq₃, which was attributed to their different molecular structures. Organic light-emitting devices (OLEDs) with emitting layer prepared by spin-coating the blends of NPB and Alq₃ exhibited a maximum luminance and a current efficiency over 10,000 cd/m² and 3.8 cd/A respectively, and when 10-(2-benzothiazolyl)-2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H,5H,11H-[l]benzopyrano[6,7,8-ij]quinolizin-11-one was doped in, a current efficiency of 8 cd/A can be obtained. Comparative device performance to the vapor-deposited OLEDs suggested that solution-process could be an alternative route for the fabrication of OLEDs based on Alq₃.