Efficient red-emitting phosphorescent iridium(III) complexes of fluorinated 2,4-diphenylquinolines

Ir(β) complexes of fluorinated dpqs(dpq-3-F, dpq-4-CF₃) as a cyclometallated ligand were prepared and their photonic properties were investigated, where dpq-3-F and dpq-4-CF₃ represent 2-(3-fluoro-phenyl)-4-phenylquinoline and 4-phenyl-2-(4-trifluoromethylphenyl)quinoline, respectively. Fluorinated dpq derivatives were introduced to the iridium complexes to increase the efficiency compared to Ir(dpq)₂(acac) which was recently reported to have emission wavelength of 614 nm with quantum efficiency of 0.14. These fluorinated ligands and their Ir(III) complexes were computationally calculated by ab initio methods to support our experimental results. It was found that the Ir complex containing dpq-3-F ligands exhibits the largest emission efficiency with maximum emission peak at 593.5 nm. The result of ab initio calculation using the time-dependent density functional theory (TD-DFT) showed that the strong ³MLCT transition of the complex occurs due to the strong coupling between the 5d orbital of the Ir atom and the highest occupied molecular orbitals (HOMOs) of these ligands.     

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.     

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.     

Strong ligand field effects of blue phosphorescent mono-cyclometalated iridium(III) complexes

A series of mono-cyclometalated blue phosphorescent iridium(III) complexes with two phosphines trans to each other and two cis-ancillary ligands, such as Ir(F₂Meppy)(PPhMe₂)₂(H)(Cl), [Ir(F₂Meppy)(PPhMe₂)₂(H)(NCMe)]⁺ and Ir(F₂Meppy)(PPhMe₂)₂-(H)(CN), [F₂Meppy = 2-(2′,4′-difluorophenyl)-4-methyl-pyridine] were synthesized and studied to tune the phosphorescence wavelength to the deep blue region and to enhance the luminescence efficiencies. We investigate the electron-withdrawing capabilities of ancillary ligands using the DFT and TD-DFT calculations on the ground and excited states of the three complexes to gain insight into the factors responsible for the emission color change and the different luminescence efficiency. Reducing the molecular weight of phosphine ligand with PPhMe₂ leads to a strategy of the efficient deep blue organic light-emitting devices (OLED) by thermal processing instead of the solution processing. The electron-withdrawing difluoro group substituted on the phenyl ring and the cyano strong field ancillary ligand in the trans position to the carbon atom of phenyl ring increased HOMO-LUMO gap and achieved the hypsochromic shift in emission color. As a result, the maximum emission spectra of Ir(F₂Meppy)(PPhMe₂)₂(H)(Cl), [Ir(F₂Meppy)(PPhMe₂)₂(H)-(NCMe)]⁺ and Ir(F₂Meppy)(PPh-Me₂)₂ (H)(CN) were in the ranges of 446, 440, 439 nm, respectively.     

Synthesis and photo physical study of iridium complex of new pentafluorophenyl-substituted ligands

New iridium complexes, [Ir(dpq)₂(acac), Ir(PF-dpq)₂(acac) and Ir(PF-dpq-5F)₂(acac)] (dpq = 2,4-diphenylquinoline, dpq-5F = 2-(3′-fluorophenyl)-4-phenylquinoline), PF-dpq-5F = 2-(3-fluoro-phenyl)-6-pentafluorophenyl-4-phenylquinoline and acac = acetylacetonate) have been synthesized and characterized for efficient red organic light-emitting diodes (OLEDs). In order to improve the luminescence efficiency by preventing self-quenching and to tune photoluminescence (PL) and electroluminescence (EL) spectra to a longer wavelength, dpq ligand was fluorinated by -PF and -F moieties. However, the iridium complex of PF-dpq-5F underwent a weak MLCT transition because of the weak coupling between the 5d orbital of the iridium atom and HOMO of the substituted ligand. Thus, the maximum luminous efficiencies of the device using Ir(dpq)2(acac), Ir(PF-dpq)₂(acac) and Ir(PF-dpq-5F)₂(acac) are 4.36 cd/A, 6.04 cd/A and 4.35 cd/A, respectively.     

New blue phosphorescent iridium complexes containing phenylpyridine and triazole ligands: synthesis and luminescence studies

The synthesis and luminescence of iridium(III) complexes containing new phenylpyridine (C(see test for symbol)N) ligands, 4-Me-4'-F-ppy, 4-Me-4'-CF3-ppy and 4-OMe-4'-CF3-ppy, were studied. These ligands were designed for development of the blue light-emitting iridium complexes by introducing the electron-withdrawing group (F, CF3) and the electron-donating group (Me, OMe) at the para positions of the phenyl and pyridine ligand rings, respectively. As an ancillary ligand, trzl-CMe3 was employed where trzl-CMe3 represents 2-(5-tert-butyl-2H-1,2,4-triazol-3-yl)pyridine. The resulting iridium complexes, Ir(4-Me-4'-F-ppy)2(trzl-CMe3), Ir(4-OMe-4'-CF3-ppy)2 (trzl-CMe3) and Ir(4-Me-4'-CF3-ppy)2(trzl-CMe3) exhibited the blue emission at 472, 484 and 494 nm in CH2Cl2 solution, respectively. Ir(4-Me-4'-F-ppy)2(trzl-CMe3) showed the most hypsochromic shift in photoluminescence (PL) among the complexes prepared herein. In the electroluminescence (EL) spectra, Ir(4-Me-4'-F-ppy)2(trzl-CMe3) and Ir(4-Me-4'-CF3-ppy)2(trzI-CMe3) exhibited the luminescence peak at 437 nm and 496 nm, respectively. In the aspect of blue emission color purity, Ir(4-Me-4'-F-ppy)2(trzl-CMe3) had the CIE coordinates of (0.176, 0.143), very close to the saturated standard blue emission.     

Synthesis and red electrophosphorescence of a novel cyclometalated iridium complex in polymer light-emitting diodes

The preparation and characterization of a new cyclometalated iridium complex with 2-(1-naphthalene) pyridine ligand were reported. An electrophosphorescent device was fabricated by using this new iridium complex as guest and poly-(cyano-paraphenylene) as host. Red electrophosphorescence was observed with an emission peak at approximately 600 nm. An external quantum efficiency of 1.3% was achieved in this electrophosphorescent polymer light-emitting devices.     

Synthesis and optoelectronic properties of oxadiazole-functionalized iridium complexes in the poly(vinylcarbazole)-hosted devices

A class of oxadiazole-functionalized iridium complexes was used as phosphor emitters in poly (vinylcarbazole)-hosted devices. Efficient green electrophosphorescences were achieved in the devices with a maximum luminance efficiency of 9.3 cd/A at 10.6 mA/cm² and brightness of 3882 cd/m² at 92.1 mA/cm². More importantly, the iridium complexes-doped devices exhibited a low turn-on voltage of 7.0 V and an applied voltage of 9.2 V at 500 cd/m². The good optoelectronic properties of the complexes were attributed to the enhanced electron-injection and transport properties resulting from the effect of oxadiazole ligands in the complexes.     

Effect of the ligand on the properties of emitting materials: Pentacoordinated 8-hydroxyquinoline aluminum complexes

Two series of pentacoordinated complexes, AlMq₂q′ and Alq₂q′ (q is 8-hydroxyquinoline, Mq is 2-methyl-8-hydroxyquinoline and q′ is phenolato ligand), were synthesized, and assessed as potential emitting materials in thin film (photoluminescence, PL) and electroluminescent (EL) device. EL devices with a configuration of ITO/NPB(50 nm)/Complex(50 nm)/Mg/Ag(10:1) were fabricated. Strong blue and green emission were observed from thin solid film and EL device of AlMq₂q′ and Alq₂q′, respectively. The results revealed that the PL and EL emission wavelengths of these materials are primarily determined by Mq and q (first ligand), whereas phenolato ligand (second ligand) has little effect on the emission wavelength but remarkable influence on EL efficiency.