Thermally stable carboline derivative as a host material for blue phosphorescent organic light-emitting diodes

A α-carboline based high triplet energy material, 9,9′-(5′-(carbazol-9-yl)-[1,1′:3′,1″-terphenyl]-3,3″-diyl)di-α-carboline (2CbCzT), was designed and synthesized as the thermally stable host material for blue phosphorescent organic light-emitting diodes (PHOLEDs). The 2CbCzT host showed high glass transition temperature of 149 °C and high decomposition temperature of 518 °C at 5% weight loss. In addition, the 2CbCzT exhibited bipolar charge transport properties due to hole transport type carbazole and electron transport type α-carboline units. Blue PHOLEDs were developed using the high triplet energy 2CbCzT host material and a high quantum efficiency of 22.1% was obtained.     

High triplet energy Al complex as a host material for blue phosphorescent organic light-emitting diodes

An Al complex, tris((2-(pyrazol-1-yl)pyridin-3-yl)oxy)aluminum (Al(pypy)₃), was synthesized as a high triplet energy host material for blue phosphorescent organic light-emitting diodes. A high triplet energy ligand, 2-(1H-pyrazol-1-yl)pyridin-3-ol, was coordinated to the Al to develop the high triplet energy host material derived from Al. The Al(pypy)₃ host showed a high triplet energy of 2.86 eV for efficient energy transfer to blue triplet emitter. A maximum quantum efficiency of 20.5% was achieved in blue device using the Al(pypy)₃ host material.     

Acridine derived stable host material for long lifetime blue phosphorescent organic light-emitting diodes

A host material having acridine as a hole transport moiety, 10-(3′-(9H-carbazol-9-yl)-[1,1′-biphenyl]-3-yl)-9,9-dimethyl-9,10-dihydroacridine (CZBPAC), was explored as the host material of phenylimidazole type Ir triplet emitter to realize both high quantum efficiency and stable operational lifetime. The acridine containing CZBPAC was superior to carbazole based host material with the same backbone structure in that it can improve driving voltage, quantum efficiency and lifetime of the blue phosphorescent organic light-emitting diodes simultaneously.     

Silicon-based carbazole and oxadiazole hybrid as a bipolar host material for phosphorescent organic light-emitting diodes

A silicon-based bipolar compound, 2-(4-((4-(9H-carbazol-9-yl)phenyl)dimethylsilyl)phenyl)-5-phenyl-1,3,4-oxadiazole (COHS), was designed and prepared as a host material for phosphorescent organic light-emitting diodes (OLEDs). The conjugated analogue of COHS, 2-(4′-(9H-carbazol-9-yl)biphenyl-4-yl)-5-phenyl-1,3,4-oxadiazole (COH), was also prepared to investigate their structure–property relationships. Thermal-, photophysical- and electrochemical properties as well as their single-crystal X-ray structures were studied for COHS and COH. The central silicon atom in COHS successfully disconnected the electronic communication between the carbazole and oxadiazole groups, resulting in relatively high triplet energy of ca. 2.71 eV, which were capable of hosting green phosphorescent emitters. DFT calculations were conducted to investigate the electronic structures of COHS and COH, and the results showed good correlation to experimental results. Finally, COHS and COH were used as a bipolar host material for a green phosphorescence organic light-emitting diode (PHOLED) devices with Ir(ppy)₃ (tris[2-phenylpyridinato-C²,N]iridium(III)) as a dopant. The resulting device with COHS (device I) showed higher performance than the device with COH (device II), exhibiting high efficiencies and low-efficiency roll-off. Device I achieved maximum external quantum efficiencies (EQE) of 15.8%, whereas device II exhibited a relatively lower EQE of 13.0%.     

High triplet energy n-type dopants for high efficiency in phosphorescent organic light-emitting diodes

High triplet energy n-type dopants, lithium 2-(oxazol-2-yl)phenolate (LiOx) and lithium 2-(1-methyl-imidazol-2-yl)phenolate (LiIm), were synthesized as n-type doping materials for phosphorescent organic light-emitting diodes and the effect of the n-type doping materials on the electron mobility and device performances of the phosphorescent organic light-emitting diodes was investigated. The LiOx and LiIm n-type dopants were effective to increase the electron mobility of electron transport materials and improve the quantum efficiency of green and blue phosphorescent organic light-emitting diodes.     

High triplet energy electron transport type exciton blocking materials for stable blue phosphorescent organic light-emitting diodes

High triplet energy electron transport materials with dibenzothiophene and dibenzofuran cores modified with a diphenyltriazine unit were investigated as electron transport type exciton blocking materials for stable blue phosphorescent organic light-emitting diodes. The two exciton blocking materials showed high triplet energy above 2.80 eV and enhanced quantum efficiency of the blue phosphorescent devices by more than 40% while maintaining stability of the pristine blue devices without the high triplet energy exciton blocking layer.     

High external quantum efficiency in yellow and white phosphorescent organic light-emitting diodes using an indoloacridinefluorene type host material

High efficiency yellow phosphorescent organic light-emitting diodes were developed using spiro[fluorene-9,8′-indolo[3,2,1-de]acridine]-2,7-dicarbonitrile (ACDCN) as the host material for yellow emitting iridium(III) bis(4-phenylthieno[3,2-c]pyridinato-N,C²′)acetylacetonate (PO-01). The ACDCN host showed bipolar charge transport properties and efficient energy transfer to PO-01 dopant. Maximum external quantum efficiency of 25.7% and external quantum efficiency of 21.9% at 1000 cd/m² were obtained using ACDCN as the host material. In addition, high external quantum efficiency of 20.9% was achieved in the two color white phosphorescent organic light-emitting diodes with the PO-01 and iridium(III) bis[(4,6-difluorophenyl)-pyridinato-N,C²]picolinate doped ACDCN emitting layer.     

Orthogonally substituted aryl derivatives as bipolar hosts for blue phosphorescent organic light-emitting diodes

Four novel bipolar hosts, namely 9,9′-(2-(4,6-diphenylpyrimidin-2-yl)-1,3-phenylene)bis(9H-carbazole) (2CzPm), 9,9′-(2-(4,6-diphenylpyrimidin-2-yl)-1,3-phenylene)bis(3,6-di-tert-butyl-9H-carbazole) (2TCzPm), 5,5′-(2-(4,6-diphenylpyrimidin-2-yl)-1,3-phenylene)bis(5H-benzofuro[3,2-c]carbazole) (2BFCzPm) and 5,5′-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)-1,3-phenylene)bis(5H-benzofuro[3,2-c]carbazole) (2BFCzTrz) were designed and synthesized with diphenylpyrimidine and diphenyltriazine as electron-transporting units and carbazole derivatives as hole-transporting motifs for the application in blue phosphorescent organic light-emitting diodes (PHOLEDs). These electron-accepting and -donating functional groups were attached to the central phenylene bridge in an ortho-substituted fashion, which led to high triplet energies (2.97–3.00 eV) and wide bandgap (3.43–3.55 eV). The effect of modulation of electron-accepting and donating groups on the photophysical properties, frontier orbital energy levels, charge carrier transport properties and device performance of these four hosts has been investigated. 2BFCzPm and 2BFCzTrz featured with large conjugation system exhibited high thermal stability as compared to 2CzPm and 2TCzPm. The bis[2-(4,6-difluorophenyl)-pyridinato-C2,N](picolinato)iridium(III) (FIrpic) based blue PHOLEDs hosted by 2BFCzPm exhibited excellent electroluminescence performance with a peak current efficiency of 38.2 cd/A and a maximum external quantum efficiency of 19.0%, which could be ascribed to the enhanced thermal stability, high triplet energy and good bipolar charge transport properties of the host material.     

High quantum efficiency in blue phosphorescent organic light emitting diodes using ortho-substituted high triplet energy host materials

A high triplet energy material derived from carbazole and ortho terphenyl, 3,3′′-di(9H-carbazole-9-yl)-1,1′:2′,1′′-terphenyl (33DCTP), was synthesized as the host material for blue phosphorescent organic light-emitting diodes (PHOLEDs). The 33DCTP host showed high glass transition temperature of 110 °C, high triplet energy of 2.77 eV, the highest occupied molecular orbital of ?6.12 eV and the lowest unoccupied molecular orbital of ?2.52 eV. High efficiency blue PHOLEDs were developed using the 33DCTP host and bis((3,5-difluorophenyl)pyridine) iridium picolinate dopant material, and high quantum efficiency of 23.7% was achieved with a color coordinate of (0.14, 0.28).     

Novel spiro-based host materials for application in blue and white phosphorescent organic light-emitting diodes

Two novel spiro-based host materials, namely 3-(9,9′-spirobi[fluoren]-6-yl)-9-phenyl-9H-carbazole (SF3Cz1) and 9-(3-(9,9′-spirobi[fluoren]-6-yl)phenyl)-9H-carbazole (SF3Cz2) were designed and synthesized. Due to the meta-linkage of spirobifluorene backbone, both SF3Cz1 and SF3Cz2 possess triplet energies over 2.70 eV, indicating they could serve as suitable hosts for blue and even white phosphorescent organic light-emitting diodes (PHOLEDs). The fabricated bis(4,6-(difluorophenyl)-pyridinato -N,C′)picolinate (FIrpic) based PHOLEDs hosted by SF3Cz1 and SF3Cz2 exhibited excellent performance with maximum external quantum efficiencies (EQEs) of 18.1% and 19.7%, respectively. Two-color warm white PHOLEDs fabricated by utilizing SF3Cz1 and SF3Cz2 as hosts also achieved high EQEs and low efficiency roll-offs. The results demonstrate that SF3Cz1 and SF3Cz2 are promising hosts for blue and white PHOLEDs.     

Design of bicarbazole type host materials for long-term stability in blue phosphorescent organic light-emitting diodes

Two bicarbazole type host materials, 9-(dibenzo [b,d]thiophen-4-yl)-9ʹ-phenyl-9H,9′H-3,3ʹ-bicarbazole (DBTBCz) and 9,9ʹ-bis(dibenzo [b,d]thiophen-4-yl)-9H,9′H-3,3ʹ-bicarbazole (DDBTBCz), were developed as lifetime enhancing host materials for blue phosphorescent organic light-emitting diodes (PhOLEDs). The DBTBCz and DDBTBCz host materials were prepared by substituting one or two dibenzothiophene units to a 3,3ʹ-bicarbazole backbone structure for the purpose of improving thermal stability and rigidity of the host materials for stable operational lifetime. Device characterization of the host materials revealed that the dibenzothiophene modification via 4- position is better than that via 2- position for improved lifetime of blue PhOLEDs.     

Triphenyl phosphine oxide-bridged bipolar host materials for green and red phosphorescent organic light-emitting diodes

Two wide band gap functional compounds of phenylbis(4-(spiro [fluorene-9,9'-xanthen]-2-yl)phenyl)phosphine oxide (2SFOPO) and (4-(9-ethyl-9H- carbazol-3-yl)phenyl)(phenyl)(4-(spiro[fluorene-9,9′-xanthen]-2-yl)phenyl)phosphine oxide (SFOPO-CZ) were designed, synthesized and characterized. Their thermal, photophysical, electrochemical properties and device applications were further investigated to correlate the chemical structure of bipolar host materials with the electroluminescent performance for phosphorescent organic light-emitting diodes (PhOLEDs). Both of them show high thermal stability with glass transition temperatures in a range of 105–122 °C and thermal decomposition temperatures at 5% weight loss in a range of 406–494 °C. The optical band gaps of compound 2SFOPO and SFOPO-CZ in CH₂Cl₂ solution are 3.46 and 3.35 eV, and their triplet energy levels are 2.51 eV and 2.52 eV, respectively. The high photoluminescent quantum efficiency of emissive layer of doped green device up to 50% is obtained. Employing the developed materials, efficient green and red PhOLED in simple device configurations have been demonstrated. As a result, the green PhOLEDs of compound SFOPO-CZ doped with tris(2-phenylpyridine) iridium shows electroluminescent performance with a maximum current efficiency (CE_max) of 52.83 cd A⁻¹, maximum luminance of 34,604 cd/m², maximum power efficiency (PE_max) of 39.50 lm W⁻¹ and maximum external quantum efficiency (EQE_max) of 14.1%. The red PhOLED hosted by compound 2SFOPO with bis(2-phenylpyridine)(acetylacetonato) iridium(III) as the guest exhibits a CE_max of 20.99 cd A⁻¹, maximum luminance of 33,032 cd/m², PE_max of 20.72 lm W⁻¹ and EQE_max of 14.0%. Compound SFOPO-CZ exhibits better green device performance, while compound 2SFOPO shows better red device performance in PhOLEDs.     

Dibenzofuran derivative as high triplet energy host material for high efficiency in deep blue phosphorescent organic light-emitting diodes

A high efficiency deep blue phosphorescent organic light-emitting diodes was developed using an weak electron transport type high triplet energy host material with dibenzofuran and phosphine oxide units. The host material showed a high triplet energy of 3.01 eV and was effective as the host material for deep blue phosphorescent organic light-emitting diodes. The device performances could be optimized by managing the doping concentration of phosphorescent dopants and a high quantum efficiency of 25.9% with a color coordinate of (0.14, 0.22) was achieved.     

Spiro-fused N-phenylcarbazole-based host materials for blue phosphorescent organic light-emitting diodes

Two host materials, SFCA and SFCC, consist of a diphenylamine or carbazole unit linking to spiro-fused phenyl carbazole (SFC) backbone, were designed and synthesized. By choosing the meta linkage way between diphenylamine/carbazole units and SFC ring, higher triplet energies could be easily achieved for the two new materials, which mean that they could be used as effective host material for popular blue phosphorescent material Iridium(III) bis[(4,6-difluorophenyl)pyridinato-N,C^2′] picolinate (FIrpic, E_T = 2.65). Besides that, the steric SFC structure could guarantee their good thermal stabilities. Their thermal, photophysical and electroluminescent properties were systematically investigated. The blue phosphorescent OLEDs with the two materials as hosts and FIrpic as a dopant exhibited excellent performance with maximum current efficiencies of 33.9 and 40.8 cd/A, respectively.     

Deep blue phosphorescent organic light-emitting diodes with excellent external quantum efficiency

Highly efficient deep blue phosphorescent organic light-emitting diodes (PHOLEDs) using two heteroleptic iridium compounds, (dfpypy)₂Ir(acac) and (dfpypy)₂Ir(dpm), as a dopant and 9-(3-(9H-carbazol-9-yl)phenyl)-9H-carbazol-3-yl)diphenylphosphine oxide as a host material have been developed. The electroluminescent device of (dfpypy)₂Ir(dpm) at the doping level of 3 wt% shows the best performance with external quantum efficiency of 18.5–20.4% at the brightness of 100–1000 cd/m² and the color coordinate of (0.14, 0.18) at 1000 cd/m².     

High efficiency deep blue phosphorescent organic light-emitting diodes

Deep blue phosphorescent organic light-emitting diodes have been developed by using tris((3,5-difluoro-4-cyanophenyl)pyridine) iridium (FCNIr) as a blue phosphorescent dopant. The FCNIr showed a wide triplet bandgap of 2.8 eV for deep blue emission due to a strong electron withdrawing CN substituent in addition to F unit. Doping of the FCNIr in N,N’-dicarbazolyl-3,5-benzene gave a high quantum efficiency of 9.2% with a CIE color coordinate of (0.15, 0.16).     

Phthalonitrile based charge transfer type host for yellow phosphorescent organic light-emitting diodes

An phthalonitrile based 3,3''-di(9H-carbazol-9-yl)-[1,1':2′,1''-terphenyl]-4′,5′-dicarbonitrile (IPNCz) was explored as a charge transfer type host of a yellow emitting bis(4-phenyl-thieno[3,2-c]pyridinato-C2,N)(acetylacetonato)iridium(III) (PO-01) dopant. The phthalonitrile unit was an electron deficient unit and 9-phenylcarbazole was an electron rich unit of the IPNCz host. The phthalonitrile unit combined with the phenylcarbazole unit allowed strong charge transfer character by the donor-acceptor structure, delivering good thermal stability, bipolar carrier transport and proper triplet energy. Therefore, the IPNCz host assisted low driving voltage and high quantum efficiency close to 25% in the yellow phosphorescent device.     

Stable efficiency roll-off in blue phosphorescent organic light-emitting diodes by host layer engineering

The device characteristics of blue phosphorescent organic light-emitting diodes (PHOLEDs) with mixed host structure were investigated by changing the combination and the composition of host materials in emissive layer. The distributed recombination zone and balanced charge carrier injection within emissive layer were achieved through mixed host optimization with a hole transport-type and an electron transport-type host materials, therefore the device performances were greatly enhanced, with external quantum and power efficiencies of 21.8% and 53 lm/W. Moreover, mixed host blue PHOLEDs exhibited a extremely low stable efficiency roll-off with quantum efficiencies of 20.3% and 18.6% at a luminance of 1000 and 10,000 cd/m².     

meta-Linked spirobifluorene/phosphine oxide hybrids as host materials for deep blue phosphorescent organic light-emitting diodes

This study investigated the use of a novel modification in molecular design to get two new electron-transport host materials, SF3PO and BSF3PO. By linking the phosphine oxide moieties at meta-position of spirobifluorene rings, higher triplet energies could be easily achieved for these two new materials. The steric spirobifluorene structures could guarantee their good thermal stabilities. According to these properties, their applications as host materials for deep blue phosphorescent organic light-emitting diodes (PHOLEDs) were explored. As expected, the deep blue emitting devices with Ir-complex FIr6 as phosphorescent dopants and SF3PO and BSF3PO as hosts had been fabricated and showed high efficiency of 28.5 and 22.0 cd/A, respectively, which were significantly higher than that of the para-linked analogue SPPO1.     

Molecular design of large-bandgap host materials and their application to blue phosphorescent organic light-emitting diodes

New large-bandgap host materials with carbazole and carboline moieties were designed and synthesized for high-performance blue phosphorescent organic light-emitting diodes (PhOLEDs). The two kinds of host materials, 9-(4-(9H-carbazol-9-yl)phenyl)-6-(9H-carbazol-9-yl)-9H-pyrido[2,3-b]indole (pP2CZCB) and 9-(3-(9H-carbazol-9-yl)phenyl)-6-(9H-carbazol-9-yl)-9H-pyrido[2,3-b]indole (mP2CZCB), displayed promisingly high triplet energies of ∼2.92–2.93 eV for enhancing the exothermic energy transfer to bis[2-(4,6-difluorophenyl)pyridinato-C²,N](picolinato)iridium(III) (FIrpic) in PhOLED devices. It was found that the blue PhOLEDs bearing the new host materials and the FIrpic dopant exhibited markedly higher external quantum efficiencies (EQEs) than a device made with 1,3-bis(N-carbazolyl)benzene (mCP) as the host. In particular, the PhOLED device made with 3 wt% FIrpic as the dopant and mP2CZCB as the host material displayed a low driving voltage of 4.13 V and the high EQE of 25.3% at 1000 cd m⁻².