Improved efficiency by doping blue iridium (III) complex in europium complex-based light-emitting diodes

We demonstrated high-efficiency red organic light-emitting diodes (OLEDs) employing a europium complex, Eu (III) tris( thenoyltrifluoroacetone) 3,4,7,8-tetramethyl-1,10-phenanthroline (Eu(TTA)(3)(Tmphen)), as an emitter and a blue electrophosphorescent complex, Iridium ( III) bis[4,6-di-fluorophenyl-pyridinato-N,C-2] picolinate (FIrpic), as an assistant dopant codoped into 4,4-N, N-dicarbazole-biphenyl (CBP) host as an emissive layer. A pure red electroluminescence (EL) only from Eu3+ ions at 612 nm with a full width at half maximum of 3 nm was observed and the EL efficiency was significantly enhanced. The maximum EL efficiency reached 7.9 cd A(-1) at 0.01 mA cm(-2) current density, which is enhanced by 2.8 times compared with electrophosphorescence-undoped devices. The large improvements are attributed to energy transfer assistance effects of FIrpic, indicating a promising method for obtaining efficient red OLEDs based on rare-earth complexes.

High efficiency tandem organic light-emitting devices with Al/WO3/Au interconnecting layer

An interconnecting layer of Al (2 nm)/WO3 (3 nm)/Au (16 nm) was studied for application in tandem organic light-emitting devices. It can be seen that the Al/WO3/Au structure plays the role of an excellent interconnecting layer. The introduction of WO3 in the connection unit significantly improves the device efficiency as compared to the case of Al/Au. Thus, the current efficiency of the two-unit tandem devices is enhanced by two factors with respect to the one-unit devices. The green two-unit tandem device of indium tin oxide/MoO3/4,4(')-N,N-'-bis[N-(1-naphthyl)-N-phenyl-amino]biphenyl(NPB)/tris(8-hydroxylquinoline) aluminum (Alq(3)):10-(2-benzothiazolyl)-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolizin-11-one (C545T)/Alq(3)/LiF/Al/WO3/Au/MoO3/NPB/Alq(3):C545T/Alq(3)/LiF/Al showed a maximum current efficiency of 33.9 cd/A and a power efficiency of 12.0 lm/W.

One-pot synthesis of polyimides via Ni-catalyzed coupling of bis(chlorophthalimide)s

A one-pot synthesis method for the preparation of polyimides containing biphenyl units was developed via nickel-catalyzed coupling reaction of bis(chlorophthalimide)s which were prepared from chloroplithalic anhydrides and diamines in xylene. The resulting polyimides had inherent viscosities of above 0.60dL g(-1). In the meantime, the copolymerizations from a mixture of three isomeric bis(chlorophthalimide)s gave the polymers with inherent viscosities of 0.36-0.55 gdL(-1). The solubility and film formability of the copolymers were better than those of homopolymers from bis(4-chlorophthalimide). The 10% weight loss of these polyimides was between 470 and 531 degrees C.

Isomeric polyimides

This review deals with polyimides based on isomeric dianhydrides and diamines, and with chiral polyimides. First, however, a summary is presented of recent work on the synthesis of isomeric dianhydrides, the reaction of mellophanic dianhydride with diamines, and the tendency toward cyclization in reactions of some dianhydrides and diamines. Then turning to polymers, the discussion covers solubility, thermal and dielectric properties, permeability and permselectivity for gas separation, and rheology of isomeric polyimides. Several useful general rules have been found: i.e. the glass transition temperature of polyimides based on isomeric dianhydrides with a given diamine decreases in the order 3,3'- > 3,4'- > 4,4-dianhydride if the polymers are of comparable molecular weight, whereas the thermal stability and the T-beta/T-g ratio (in absolute temperatures) increase in the order of 3,3'- < 3,4'- < 4,4'-dianhydride. Polyimides from 3,3'- or 3,4'-dianhydride have higher solubility than those from 4,4'-dianhydride. Polyimides from 3,4'-dianhydrides exhibit much lower melt viscosity than those from the other isomeric anhydrides. The dielectric constants of polyimides derived from m,m'-diamines are lower than those from p,p'-diamines. Polyimides based on 3,3'- or 3,4'-dianhydrides have higher permeability and slightly lower permselectivity than polyimides based on 4,4'-dianhydrides.

Structure and liquid crystalline properties of 5-[(4 '-heptoxy-4-biphenylyl)carbonyloxy]-1-pentyne

The crystal structure and liquid crystalline properties of a biphenyl-containing acetylene, [5-[(4'-heptoxy-4- biphenylyl) carbonyloxy]-1-pentyne (A3EO7) were investigated by electron crystallography, X-ray diffraction, polarizing optical microscopy, differential scanning calorimetry, transmission electron microscopy, and atomic force microscopy. A3EO7 crystals obtained from a toluene solution adopts a monoclinic P112/m space group with unit cell parameters of a = 6.25 Angstrom, b = 7.82 Angstrom, c = 46.70 Angstrom and gamma = 96.7degrees, as determined using electron diffraction. Upon cooling from the isotropic phase, A3EO7 exhibits a smectic A phase in the temperature range 72.4 - 53.6degreesC. Further lowering of the temperature results in the formation of a smectic C phase which exhibits a strong tendency towards crystallization.

Modeling of organic light-emitting diodes with graded concentration in the emissive multilayer

We model the electrical behavior of organic light-emitting diodes whose emissive multilayer is formed by blends of an electron transporting material, tris-(8-hydroxyquinoline) aluminum (Alq(3)) and a hole transporting material, N,N-'-diphenyl-N,N-'-bis(1,1(')-biphenyl)-4,4-diamine. The multilayer is composed of layers of different concentration. The Alq(3) concentration gradually decreases from the cathode to the anode. We demonstrate that these graded devices have higher efficiency and operate at lower applied voltages than devices whose emissive layer is made of nominally homogeneous blends. Our results show an important advantage of graded devices, namely, the low values of the recombination rate distribution near the cathode and the anode, so that electrode quenching is expected to be significantly suppressed in these devices.

Novel hole-transporting materials based on 1,4-bis(carbazolyl)benzene for organic light-emitting devices

Novel hole-transporting molecules containing 1,4-bis(carbazolyl)benzene as a central unit and different numbers of diphenylamine moieties as the peripheral groups have been synthesized and characterized. These compounds are thermally stable with high glass transition temperatures of 141-157 degreesC and exhibit chemically reversible redox processes. Their amorphous state stability and hole transport properties can be significantly improved by increasing the number of diphenylamine moieties in the outer part and by controlling the symmetry of the carbazole-based molecules. These compounds can be used as good hole-tran sporting materials for organic electroluminescent (EL) devices. The device performance based on tri- and tetra-substituted carbazole derivatives is comparable to that of a typical 4,4'-bis[N-(1-naphthyl)-N-phenylamino] biphenyl (NPB)-based device.

Synthesis and properties of soluble polyimides based on isomeric ditrifluoromethyl substituted 1,4-bis(4-aminophenoxy)benzene

A new fluorinated diamine monomer, [1,4-bis(4-amino-3-trifluoromethylphenoxy)benzene (2)], and a known isomeric analog 1,4-bis(4-amino-2-trifluoromethylphenoxy)benzene (3) were synthesized. A series of organosoluble polyimides Ia-d and IIa were prepared from the diamines (2, 3) and dianhydrides (a-d) by a high-temperature one-step method. The effects of the trifluoromethyl substituents on the properties of polyimides were evaluated through the study of their soluble, thermal, optical, and gas permeability properties. Polyimides (Ia-d) had glass transition temperatures between 229 and 279 degrees C, and the temperatures at 5% weight loss ranged from 510 to 533 degrees C under nitrogen. These polyimides could be cast into flexible and tough membranes from DMAc solutions. The membranes had tensile strengths in the range of 137-169 MPa, tensile modulus in the range of 1.6-2.2 GPa and elongations at break from 11% to 14%. The polyimide la with trifluoromethyl groups ortho to the imide nitrogen exhibited enhanced gas permeability, solubility, transparency, and thermal stability compared with the isomeric polyimide IIa with the CF3 group meta to the imide nitrogen.

Surface-appropriate lipophobicity - Application in isobutene oligomerization over Teflon-modified silica-supported 12-silicotungstic acid

A series of silica-supported 12-silicotungstic acid catalysts (H4SiW12O40, abbreviated as HSiW), modified with various loadings of Teflon (HSiW/SiO2-Teflon), were prepared by an impregnation method. The surface properties of the catalysts were studied by means of X-ray diffraction (XRD), scanning electron microscopy (SEM), BET, infrared (IR) spectroscopy, NH3-TPD and the Drop Shape Analysis (DSA). SEM results combined with energy-dispersive X-ray (EDX) measurements of HSiW/SiO2-Teflon revealed that F-compound (Teflon) is effectively coated on the catalyst surface. The contact angles for water and oil of 50 wt% HSiW/SiO2 and HSiW/SiO2-Teflon indicate that HSiW/SiO2-Teflon catalyst enhances not only the surface hydrophobicity but also the surface lipophobicity by means of the addition of Teflon. Silica-supported 12-silicotungstic acid modified with Teflon exhibits higher C-8(=) selectivity and longer lifetime than that of silica-supported 12-silicotungstic acid in isobutene oligomerization. Thus, surface-appropriate lipophobicity of catalysts may be effective for decreasing the interaction between coke precursors and the catalyst surface and for removing deposited coke more easily.

Improved performance and stability by an Al/Ni bilayer cathode in organic light-emitting diodes

Al/Ni bilayer cathode was used to improve the electroluminescent (EL) efficiency and stability in N,N'-bis(1-naphthyl)-N,N'-diphenyl-1,1' biphenyl 4,4'-dimaine (NPB)/tris-(8-hydroxyquinoline) aluminum (Alq(3))-based organic light-emitting diodes. The device with LiF/Al/Ni cathode achieved a maximum power efficiency of 2.8 lm/W at current density of 1.2 mA/cm(2), which is 1.4 times the efficiency of device with the state-of-the-art LiF/Al cathode. Importantly, the device stability was significantly enhanced due to the utilization of LiF/Al/Ni cathode. The lifetime at 30% decay in luminance for LiF/Al/Ni cathode was extrapolated to 400 It at an initial luminance of 100 cd/m(2), which is 10 times better than the LiF/Al cathode.

NaCl/Ca/Al as an efficient cathode in organic light-emitting devices

An efficient cathode NaCl/Ca/Al used to improve the performance of organic light-emitting devices (OLEDs) was reported. Standard NM-bis(1-naphthyl)-NAP-diphenyl-1,1' biphenyl 4,4'-dimaine (NPB)/tris-(8-hydroxyquinoline) aluminum (Alq(3)) devices with NaCl/Ca/Al cathode showed dramatically enhanced electroluminescent (EL) efficiency. A power efficiency of 4.6 lm/W was obtained for OLEDs with 2 nm of NaCl and 10 nm of Ca, which is much higher than 2.0 lm/W, 3.1 lm/W, 2.1 lm/ W and 3.6 lm/W in devices using, respectively, the LiF (1 nm)/Al, LiF (1 nm)/Ca (10 nm)/Al, Ca (10 nm)/Al and NaCl (2 nm)/ Al cathodes. The investigation of the electron injection in electron-only devices indicates that the utilization of the NaCl/Ca/Al cathode substantially enhances the electron injection current, which in case of OLEDs leads to the improvement of the brightness and efficiency.

High efficiency white organic light-emitting diodes based on double recombination zones

A multilayer white organic light-emitting diode (OLED) with high efficiency was present. The luminescent layer was composed of a red dye 4-(dicyanomethylene)-2-t-butyle-6-(1,1,7,7-tetra-methyljulolidyl-9-enyl)-4H-pyran (DCJTB) doped into NN-bis-(1-naphthyl)-N,N-diphenyl-1,1-biphenyl-4-4-diamine (NPB) layer and a blue-emitting 9,10-bis-(beta-naphthyl)-anthrene (DNA) layer. Red and blue emission, respectively, from DCJTB:NPB and DNA can be obtained by effectively controlling the thicknesses of DCJTB:NPB and DNA layers, thus a stable white light emission was achieved. The device turned on at 3.5 V, and the maximum luminance reached 16000 cd/m(2) at 21 V. The maximum current efficiency and power efficiency were 13.6 cd/A and 5.5 lm/W, respectively.

Syntheses and properties of polyimides derived from diamines containing 2,5-disubstituted pyridine group

A Series of novel homo- and copolyimides containing pyridine units were prepared from the heteroaromatic diamines, 2,5-bis (4-aminophenyl) pyridine and 2-(4aminophenyl)-5-aminopyridine, with pyromelltic dianhydride (PMDA), and 3,3',4,4'-biphenyl tertracarboxylic dianhydride (BPDA) via a conventional two-step thermal imidizaton method. The poly(amic acid) precursors have inherent viscosities of 1.60-9.64 dL/g (c = 0.5 g/dL in DMAC, 30 degrees C) and all of them can be cast and thermally converted into flexible and tough polyimide films. All of the polyimides show excellent thermal stability and mechanical properties. The polyimides have 10% weight loss temperature in the range of 548-598 degrees C in air. The glass transition temperatures of the PMDA-based samples are in the range of 395-438 degrees C, while the BPDA-based polyimides show two glass transition temperatures (T(g)1 and T(g)2), ranging from 268 to 353 degrees C and from 395 to 418 degrees C, respectively. The flexible films possess tensile modulus in the range of 3.42-6.39 GPa, strength in the range of 112-363 MPa and an elongation at break in the range of 1.2-69%. The strong reflection peaks in the wide-angle X-ray diffraction patterns indicate that the polyimides have a high packing density and crystallinity.

Syntheses and properties of novel polyimides derived from 2-(4-aminophenyl)-5-aminopyrimidine

2-(4-Aminophenyl)-5-aminopyrimidine (4) is synthesized via a condensation reaction of vinamidium salts and amidine chloride salts, followed by hydrazine palladium catalyzed reduction. A series of novel homo- and copolyimides containing pyrimidine unit are prepared from the diamine and 1,4-phenylenediamine (PDA) with pyromellitic dianhydride (PMDA) or 3,3',4,4'-biphenyl tertracarboxylic dianhydride (BPDA) via a conventional two-step thermal imidization method. The poly(amic acid) precursors had inherent viscosities of 0.97-4.38 dL/g (c = 0.5 g/dL, in DMAc, 30 degrees C) and all of them could be cast and thermally converted into flexible and tough polyimide films. All of the polyimides showed excellent thermal stability and mechanical properties. The glass transition temperatures of the resulting polyimides are in the range of 307-434 degrees C and the 10% weight loss temperature is in the range of 556-609 degrees C under air. The polyimide films possess strength at break in the range of 185-271 MPa, elongations at break in the range of 6.8-51%, and tensile modulus in the range of 3.5-6.46 GPa. The polymer films are insoluble in common organic solvents, exhibiting high chemical resistance.

Phase structure and transition behavior of a liquid crystal 5-{[(4 '-heptoxy-4-biphenylyl)oxy]carbonyl}-1-pentyne

The phase structures and transition behaviors of a novel liquid crystal compound containing biphenylyl mesogen, 5-{[(4'-heptoxy-4-biphenytyl) oxy]carbonyl}-1-pentyne (A3E'O7), have been investigated by differential scanning calorimetry (DSC), polarizing optical microscopy (POM) and wide angle X-ray diffraction (WAXD). In contrast to the published compound 5- {[(4'-heptoxy-4-biphenyl-yl)carbonyl]oxy}-1-pentyne (A3EO7), in which the ester bridge between the mesogenic core and the flexible spacer has different linkage order, A3E'O7 shows strikingly different phase structure and transition behaviors. Overall, A3E'O7 has better packing order and higher transition temperatures. It undergoes three enantiotropic stable liquid crystalline phases which are associated to smectic A (S-A) phase (100.2-98.2 degrees C), smectic C (S-C) phase (98.2-87.2 degrees C) and highly ordered smectic X (S-X) phase (87.2-63.3 degrees C), respectively, till eventual crystallization takes place upon cooling from isotropic state to room temperature. However, A3EO7 only shows monotropic SA (72.4-53.6 degrees C) phase and the metastable monotropic S-C phase provided that the same thermal treatment is applied.