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 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 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).     

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.     

Thermally stable indoloacridine type host material for high efficiency blue phosphorescent organic light-emitting diodes

High triplet energy materials derived from carbazole or α-carboline modified indoloacridine were synthesized and device characteristics of blue triplet emitter doped devices were investigated. The indoloacridine derived host materials showed a high triplet energy above 2.80 eV and a high glass transition temperature over 170 °C due to rigid nature of the molecular structure. The indoloacridine based host materials could approach high external quantum efficiency above 20% in blue phosphorescent organic light-emitting diodes.     

CN decoration of dibenzofuran modified biphenyl for high triplet energy host for blue phosphorescent organic light-emitting diodes

A strongly electron deficient and high triplet energy host for blue emitters was developed by decorating a dibenzofuran modified biphenyl backbone structure with multiple CN units. Two hosts, 6,6′-bis(6-cyanodibenzo[b,d]furan-4-yl)-[1,1′-biphenyl]-3,3′-dicarbonitrile(CNDBF1) and 2,2′-bis(6-cyanodibenzo[b,d]furan-4-yl)-[1,1′-biphenyl]-4,4′-dicarbonitrile(CNDBF2), were derived from the CN decoration strategy for application in blue organic light-emitting diodes requiring high triplet energy host. They showed high triplet energy above 2.79 eV and acted as the electron transport type host based on the strong electron deficiency. The mixture of the CNDBF1 and CNDBF2 hosts with a hole transport type 3,3′-di(9H-carbazol-9-yl)-1,1′-biphenyl host performed as the exciplex host of a blue phosphor and accomplished high external quantum efficiency of 22.7% in the blue phosphorescent organic light-emitting diodes.     

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%.     

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.     

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.     

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.     

9-(Pyridin-3-yl)-9H-carbazole derivatives as host materials for green phosphorescent organic light-emitting diodes

9-(Pyridin-3-yl)-9H-carbazole (PyCz) derivatives were synthesized as bipolar host materials for green phosphorescent organic light-emitting diodes (PHOLEDs) and the device performance was investigated. The PyCz core was modified with carbazole and diphenylamine to prepare the bipolar host materials. Bipolar charge transport properties were observed in the PyCz derivative with the carbazole unit and a high quantum efficiency of 21.3% was obtained in green PHOLEDs.     

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.     

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.     

High quantum efficiency and color stability in white phosphorescent organic light-emitting diodes using carboline derivative as a host material

Highly efficient and color stable phosphorescent white organic light-emitting diodes were developed using a high triplet energy host material, 3,3′-bis(9H-pyrido[2,3-b]indol-9-yl)-1,1′-biphenyl (CbBPCb), derived from carboline. Two color phosphorescent white organic light-emitting diodes were fabricated by co-doping of blue and orange triplet emitters or double emitting layer structure of blue and orange emitting layers. High quantum efficiency above 20% and color stability were achieved in the white device by optimizing the doping concentration and emitting layer thickness.     

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.     

High triplet energy exciton blocking materials based on triphenylamine core for organic light-emitting diodes

A series of novel high triplet energy materials have been designed and synthesized from the simple starting compounds through a simple one-step Friedel–Crafts reaction by using triphenylamine and methoxy, fluoro substituted diphenylmethanoles and triphenylmethanol as the starting materials. The synthesized compounds exhibit the ionization potentials in an interval of 5.4–5.7 eV in the solid state, the wide bang-gaps of 3.6 eV and the high triplet energies of about 3.0 eV. The photophysical properties have been confirmed by DFT. The introduction of a material with the lowest ionization potential as the high triplet energy exciton blocking thin layer of the green organic light-emitting diode doubled the quantum efficiency of the device. The best fabricated green device exhibited the maximum current, power, and external quantum efficiencies of 80.1 Cd A⁻¹ and 31.4 Lm W⁻¹, 23.2%, respectively. The triplet-triplet annihilation and triplet-polaron quenching effects for the devices without and with exciton blocking layer have been analyzed.     

High efficiency pure white organic light-emitting diodes using a diphenylaminofluorene-based blue fluorescent material

High efficiency pure white organic light-emitting diodes (WOLEDs) were developed using a highly efficient diphenylaminofluorene-based deep blue fluorescent material (DAF). A high quantum efficiency of 7.1% with color coordinates of (0.15, 0.18) were obtained from the DAF-doped blue device, which was then combined with phosphorescent red/green devices. A mixed interlayer was used to control the color coordinates and charge balance in the emitting layer of the WOLEDs. The pure white hybrid WOLEDs showed a high quantum efficiency of 12.3%.     

A hole transport material with ortho- linked terphenyl core structure for high power efficiency in blue phosphorescent organic light-emitting diodes

A hole transport material for use in blue phosphorescent organic light-emitting diodes was developed using an ortho linked terphenyl core structure. The ortho linked terphenyl core was modified with ditolylamine to yield the N⁴,N⁴,N^4″,N^4″-tetra-p-tolyl-[1,1′:2′,1″-terphenyl]-4,4″-diamine (TTTDA) hole transport material. TTTDA was compared with common 1,3-bis(N-carbazolyl)benzene (mCP) and showed lower driving voltage and higher power efficiency than mCP. The driving voltage was decreased by as much as 1.5 V and the power efficiency was improved by 25%.     

Interlayer free hybrid white organic light-emitting diodes with red/blue phosphorescent emitters and a green thermally activated delayed fluorescent emitter

Two different hybrid white organic light-emitting diodes (WOLEDs) with red/blue phosphorescent emitters and a green thermally activated delayed fluorescent (TADF) emitter were designed to develop high efficiency hybrid WOLEDs. One hybrid WOLED (type I) had a device structure with a hybrid emitting layer of green TADF and red phosphorescent emitters stacked on a blue phosphorescent emitting layer and the other hybrid WOLED (type II) had a device architecture with the green TADF emitting layer stacked on a red and blue phosphorescent emitting layer. Efficient energy transfer from the green TADF emitter to the red phosphorescent emitter was observed and balanced white emission could be obtained by optimizing the device structure of the hybrid WOLEDs. A quantum efficiency of 16.2% with a color coordinate of (0.45,0.47) and a quantum efficiency of 18.0% with a color coordinate of (0.37,0.47) were achieved in the type I and type II hybrid WOLEDs, respectively.     

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.