Synthesis and Application of Thiadiazoloquinoxaline-Containing Chromophores as Dopants for Efficient Near-Infrared Organic Light-Emitting Diodes

series of a donor-acceptor-donor type of near-infrared (NIR) fluorescent chromophores based on [1,2,5]thiadiazolo[3,4-g]quinoxaline (TQ) as an electron acceptor and triphenylamine as an electron donor are synthesized and characterized. By introducing pendent phenyl groups or changing the pi-conjugation length in the TQ core, we tuned tile energy levels of these chromophores, resulting in the NIR emission in a range from 784 to 868 nm. High thermal stability and glass transition temperatures allow these chromophores to be used as dopant emitters, which can be processed by vapor deposition for the fabrication of organic light-emitting diodes (OLEDs) having the multilayered structure of ITO/MoO3/NPB/Alq(3):dopant emitter/BCP/Alq(3)/LiF/Al. The electroluminescence spectra of the devices based on these new chromophores cover a range from 748 to 870 nm. With 2 wt % of dopant 1, the LED device shows an exclusive NIR emission at 752 nm with the external quantum efficiency (EQE) as high as 1.12% over a wide range of current density (e.g., around 200 mA cm(-2)).

Bridged triphenylamines as novel host materials for highly efficient blue and green phosphorescent OLEDs

Two bridged triphenylamine-triphenylsilane (BTPASi) hybrids have been designed as host materials for phosphorescent OLEDs; devices with the novel host materials achieve maximum external quantum efficiencies as high as 15.4% for blue and 19.7% for green electrophosphorescence.

Novel Oligo-9,9 '-spirobifluorenes through ortho-Linkage as Full Hydrocarbon Host for Highly Efficient Phosphorescent OLEDs

4-Bromo-9,9'-spirobifluorene is facilely synthesized, and from this precursor, two ortho-linked oligo-9,9'-spirobifluorenes, 44BSF and 24TSF, are constructed. Devices with 24TSF as the full-hydrocarbon host material and Ir(ppy)(3) or (ppq)(2)Ir(acac) as the triplet emitter show maximum external quantum efficiencies of 12.6 and 10.5% for green and red electrophosphorescence, respectively.

A Fully Diarylmethylene-Bridged Triphenylamine Derivative as Novel Host for Highly Efficient Green Phosphorescent OLEDs

A fully diarylmethylene-bridged triphenylamine derivative is efficiently synthesized. It has an almost planar triphenylamine (TPA) skeleton and exhibits excellent thermal and morphological stability. Devices with the novel TPA derivative as host material and Ir(ppy)(3) as triplet emitter show a maximum current efficiency of 83.5 cd/A and a maximum power efficiency of 71.4 Im/W for green electrophosphorescence.

Diarylmethylene-bridged 4,4 '-(bis(9-carbazolyl))biphenyl: morphological stable host material for highly efficient electrophosphorescence

novel compound (BCBP) based on the modification of a well-known host material 4,4'-(bis(9-carbazolyl))biphenyl (CBP) through arylmethylene bridge linkage was synthesized, and fully characterized. Its thermal, electrochemical, electronic absorption and photoluminescent properties were studied. A high glass transition temperature (T-g) of 173 degrees C is observed for BCBP due to the introduction of the bridged structure, remarkably contrasting with a low T-g of 62 degrees C for CBP. Furthermore, the bridged structure enhances the conjugation and raises the HOMO energy, thus facilitating hole-injection and leading to a low turn-on voltage in an electroluminescent device. With the device structure of ITO/MoO3/NPB/Ir complex: BCBP/BCP/Alq(3)/LiF/Al, maximum power efficiencies of 41.3 lm/W and 6.3 lm/W for green- and blue-emitting OLED were achieved, respectively.

Nonconjugated Carbazoles: A Series of Novel Host Materials for Highly Efficient Blue Electrophosphorescent OLEDs

A series of carbazole derivatives was synthesized and their electrical and photophysical properties were investigated. It is shown that the triplet energy levels of these hosts are higher than that of the most popular blue phosphorescent material iridium(III) bis[(4,6-difluorophenyl)pyridinato-N,C-2'] picolinate (FIrpic) and the most extensively used phosphorescent host material 4,4'-N,N'-dicarbazole-biphenyl (CBP). These new host materials also showed good thermal stability and high glass transition temperatures (T-g) ranging from 78 to 115 degrees C as the linkage group between the carbazoles was altered. Photophysical measurements indicate that the energy transfer between these new hosts and FIrpic is more efficient than that between CBP and FIrpic. Devices incorporating these novel carbazole derivatives as the host material doped with FIrpic were fabricated with the configurations of ITO/NPB (40 nm)/host:FIrpic (30 nm)/BCP (15 nm)/AlQ (30 nm)/LiF (1 nm)/Al (150 nm). High efficiencies (up to 13.4 cd/A) have been obtained when 1,4-bis (4-(9H-carbazol-9-yl)phenyl)cyclohexane (CBPCH) and bis(4-(9H-carbazol-9-yl)phenyl) ether (CBPE) were used as the host, respectively.

Tuning the Energy Level of Organic Sensitizers for High-Performance Dye-Sensitized Solar Cells

Cost-effective organic sensitizers will play a pivotal role in the future large-scale production and application of dye-sensitized solar cells. Here we report two new organic D-pi-A dyes featuring electron-rich 3,4-ethylenedioxythiophene- and 2,2'-bis(3,4-ethylenedioxythiophene)-conjugated linkers, showing a remarkable red-shifting of photocurrent action spectra compared with their thiophene and bithiophene counterparts. On the basis of the 3-f{5'-[N,N-bis(9,9-dimethylfluorene-2-yl)phenyl]-2,2'-bis(3,4-ethylenedioxythiophene)-5-yl}2-cyanoacrylic acid dye, we have set a new efficiency record of 7.6% for solvent-free dye-sensitized solar cells based on metal-free organic sensitizers. Importantly, the cell exhibits an excellent stability, keeping over 92% of its initial efficiency after 1000 h accelerated tests under full sunlight soaking at 60 degrees C. This achievement will considerably encourage further design and exploration of metal-free organic dyes for higher performance dye-sensitized solar cells.

Novel, highly efficient blue-emitting heteroleptic iridium(III) complexes based on fluorinated 1,3,4-oxadiazole: tuning to blue by dithiolate ancillary ligands

Novel blue-emitting phosphorescent iridium(III) complexes with fluorinated 1,3,4-oxadiazole derivatives as cyclometalated ligands and dithiolates as ancillary ligands have been synthesized and fully characterized; highly efficient OLEDs have been achieved using these complexes in the light-blue to blueemitting region.

Molecular design on highly efficient white electroluminescence from a single-polymer system with simultaneous blue, green, and red emission

A highly efficient white electroluminescent polymer with simultaneous blue, green, and red emission is reported, developed using a dopant/host strategy by covalently attaching both a green- and a red-light-emitting dopant to the side chain of a blue-light-emitting polymer host (see figure). In a single-layer device a maximum luminance efficiency of 7.3 cd A(-1) with CIE coordinates of (0.31,0.32) is achieved.

Highly efficient green-emitting phosphorescent iridium dendrimers based on carbazole dendrons

Green-emitting iridium dendrimers with rigid hole-transporting carbazole dendrons are designed, synthesized, and investigated. With second-generation dendrons, the photoluminescence quantum yield of the dendrimers is up to 87% in solution and 45% in a film. High-quality films of the dendrimers are fabricated by spin-coating, producing highly efficient. non-doped electrophosphorescent organic light-ernitting diodes (OLEDs). With a device structure of indium tin oxide/poly(3,4-ethylenedioxythiopheiie):poly(styrene sulfonic acid)/neat dendrimer/1,3,5-tris(2-N-phenylbenzimidazolyl)benzene/LiF/Al, a maximum external quantum efficiency (EQE) of 10.3% and a maximum luminous efficiency of 34.7 cd A(-1) are realized. By doping the dendrimers into a carbazole-based host, the maximum EQE can be further increased to 16.6%. The integration of rigid hole-transporting dendrons and phosphorescent complexes provides a new route to design highly efficient solution-processable dendrimers for OLED applications.

Highly efficient pure-white-light-emitting diodes from a single polymer: Polyfluorene with naphthalimide moieties

Light-emitting diodes exhibiting efficient pure-white-light electroluminescence have been successfully developed by using a single polymer: polyfluorene derivatives with 1,8-naphthalimide chromophores chemically doped onto the polyfluorene backbones. By adjusting the emission wavelength of the 1,8-naphthalimide components and optimizing the relative content of 1,8-naphthalimide derivatives in the resulting polymers, white-light electroluminescence from a single polymer, as opposed to a polymer blend, has been obtained in a device with a configuration of indium tin oxide/poly(3,4-ethyleiledioxythiophene)(50 nm)/polymer(80 nm)/Ca(10 nm)/Al(100 nm). The device exhibits Commission Internationale de I'Eclairage coordinates of (0.32,0.36), a maximum brightness of 11900 cd m(-2), a current efficiency of 3.8 cd A(-1), a power efficiency of 2.0 lm W-1. an external quantum efficiency of 1.50 %, and quite stable color coordinates at different driving voltages, even at high luminances of over 5000 cd m(-2).

Poly(aryl ether)s containing ter- and pentafluorene pendants for efficient blue light emission

Four novel thermally stable poly(aryl ether)s, e.g., P3F, P5F, P2A3F, and P2A5K containing ter- or pentafluorene units in the side chains for efficient blue light emission have been designed and synthesized. All the polymers show the optical properties identical to the corresponding monomers and are amorphous with higher glass transition temperature (T-g) than their monomeric Counterparts. The polymer light-emitting diodes (PLEDs) were fabricated with the device structure of ITO/(PEDOT:PSS)/polymer/Ca/Al. The incorporation of diphenylamine group to oligofluorene terminals significantly reduces the hole-injection energy barrier in PLEDs. The devices based on P2A3F and P2A5F show the luminous efficiencies of 1.2 and 2.0 cd/A at a brightness of 300 cd/m(2) with the Commission Internationale de L'Eclairage (CIE) coordinates of (0.15, 0.13) and (0.19, 0.20), respectively. All these indicate that the high-performance light-emitting polymers can be synthesized with the traditional condensation polymerization through careful design of polymer structures.

Highly efficient green light emitting polyfluorene incorporated with 4-diphenylamino-1,8-naphthalimide as green dopant

The dopant/host methodology, which enables efficient tuning of emission color and enhancement of the electroluminescence (EL) efficiency of organic light emitting diodes (OLEDs) based on small molecules, is applied to the design and synthesis of highly efficient green light emitting polymers. Highly efficient green light emitting polymers were obtained by covalently attaching just 0.3-1.0 mol% of a green dopant, 4-(N,N-diphenyl) amino-1,8-naphthaliniide (DPAN), to the pendant chain of polyfluorene (the host). The polymers emit green light and exhibit a high photoluminescence (PL) quantum yield of Lip to 0.96 in solid films, which is attributed to the energy transfer from the polyfluorene host to the DPAN dopant unit. Single layer devices (device configuration: ITO/PEDOT/Polymer/Ca/Al) of the polymers exhibit a turn on voltage of 4.8 V, luminance efficiency of 7.43 cd A(-1), power efficiency of 2.96 lm W-1 and CIE coordinates at (0.26, 0.58). The good device performance can be attributed to the energy transfer and charge trapping from the polyfluorene host to the DPAN dopant unit as well as the molecular dispersion of the dopant in the host.

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.

Highly efficient phosphorescent bis-cyclometalated iridium complexes based on quinoline ligands

The synthesis and electrochemical and photophysical study of a series of bis-cyclometalated iridium(III) complexes based on quinoline ligands have been carried out. These complexes are found to emit red-orange to deep red phosphorescence with high quantum yield and short lifetime. The red organic light-emitting diodes (OLEDs) with the external quantum efficiency up to 11.3% were demonstrated. Slow decay of efficiency with increasing current density was observed. These indicate that quinoline-based iridium complexes are promising candidates for efficient red emitters.