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1.
A series of thiophene‐containing photoactive copolymers consisting of alternating conjugated and nonconjugated segments were synthesized. The 1H NMR spectra corroborated the well‐defined structures, and the copolymers not only were soluble in common organic solvents but also had high glass‐transition temperatures (ca. 130 °C) and good thermal stability up to 390 °C. Introducing aliphatic functional groups, such as alkyl or alkoxyl, into chromophores of the copolymers redshifted the photoluminescence spectra and lowered the optical bandgaps. The electrochemical bandgaps calculated from cyclic voltammetry agreed with the optical bandgaps and thus indicated that electroluminescence and photoluminescence originated from the same excited state. The energy levels (highest occupied molecular orbital and lowest unoccupied molecular orbital) of all the copolymers were lower than those of poly[2‐methoxy‐5‐(2′‐ethylhexyloxy)‐1.4‐phenylenevinylene] MEH–PPV, indicating balanced hole and electron injection, which led to improved performance in both single‐layer and double‐layer polymeric‐light‐emitting‐diode devices fabricated with these copolymers. All the copolymers emitted bluish‐green or green light above the threshold bias of 5.0 V under ambient conditions. At the maximum bias of 10 V, the electroluminescence of a device made of poly(2‐{4‐[2‐(3‐ethoxy phenyl)ethylene]phenyl}‐5‐{4‐[2‐(3‐ethoxy,4‐1,8‐octanedioxy phenyl)ethylene]phenyl}thiophene) was 5836 cd/m2. The external electroluminescence efficiency decreased with the lifetime as the polymer degraded. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 3954–3966, 2004  相似文献   

2.
We report on photocrosslinkable hole‐transport polymers and their use as photodefinable hole‐transport layers in organic light‐emitting diodes. The polymers were obtained by copolymerization of bis(diarylamino)biphenyl‐based acrylate monomers with cinnamate‐functionalized acrylate moieties. Polymers with a range of redox potentials were obtained by varying the substitution patterns of the bis(diarylamino)biphenyl units. The 2 + 2 cycloaddition of the cinnamate moieties following UV irradiation renders the material insoluble. This allows for patterning of the polymer and simultaneously enables the fabrication of multilayer structures from solution. Hole mobilities were measured in these copolymers with the time‐of‐flight technique. Their performance as hole‐transport layers in light‐emitting diodes, with tris(8‐hydroxyquinolinato)aluminum as the emitter and electron‐transport layer, is evaluated. Electroluminescent devices with multiple hole‐transport layers having different ionization potentials were fabricated from solution, and the quantum efficiency of these devices was greater than that for devices based on a single hole‐transport layer. © 2003 Wiley Periodicals, Inc. J Polym Sci Part B: Polym Phys 41: 2726–2732, 2003  相似文献   

3.
In this study, we set out the steps to efficiently synthesize boron subphthalocyanine (BsubPc)‐containing polymers while circumventing the formation of a known side product. The synthesis was achieved using the post‐polymerization coupling reaction of a carboxylic acid functional prepolymer with bromo‐BsubPc. We have earlier shown that when copolymerizing styrene and acrylic acid (AA) a significant amount of an undesired side product is formed. In this study, we have determined that this side product persisted when styrene was copolymerized with AA or n‐butyl acrylate but could be avoided when styrene was copolymerized with methacrylic acid (MAA), methyl methacrylate, or acrylonitrile. Therefore, MAA/styrene copolymer, synthesized by nitroxide‐mediated polymerization was chosen to be coupled to BsubPc. The resulting BsubPc polymer was found to have similar electrochemical properties, solution state absorption and photoluminescence characteristics when compared against a small molecule model compound although the solid‐state PL emission of the polymer was found to be excitation wavelength dependent. Finally, preliminary organic light‐emitting diodes (OLEDs) were fabricated to assess the potential role(s) of the BsubPc polymer in organic electronic devices. These OLEDs represent the first‐solution processed organic electronic devices containing BsubPc polymers as a functional material. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2015 , 53, 1996–2006  相似文献   

4.
Two PPV‐based bipolar polymers containing 1,3,4‐oxadiazole pendant groups were synthesized via the Gilch polymerization reaction for use in light‐emitting diodes (LEDs). The resulting polymers were characterized using 1H and 13C NMR, elemental analysis, DSC, and TGA. These polymers were found to be soluble in common organic solvents and are easily spin‐coated onto glass substrates, producing high optical quality thin films without defects. The electro‐optical properties of ITO/PEDOT/polymer/Al devices based on these polymers were investigated using UV‐visible, PL, and EL spectroscopy. The turn‐on voltages of the OC1Oxa‐PPV and OC10Oxa‐PPV devices were found to be 8.0 V. The maximum brightness and luminescence efficiency of the OC1Oxa‐PPV device were found to be 544 cd/m2 at 19 V and 0.15 cd/A, respectively. © 2007 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 1098–1110, 2008  相似文献   

5.
We synthesized new polynorbornene dicarboximide (PCaNI) functionalized with hole‐transporting carbazole moieties and its copolymer (PCaNA) by ring‐opening metathesis polymerization (ROMP), where the PCaNA was further reacted with 3‐amino‐triethoxysilane to prepare PCaNI/silica hybrid. We also investigated the feasibility of PCaNI and PCaNI/silica hybrid (PCaSi) as a hole‐transporting material for hybrid organic light emitting devices (HOLEDs). To improve the performance of the PCaNI‐based HOLEDs, N,N′‐diphenyl‐N,N′‐(3‐methylphenyl)‐[1,1′‐biphenyl]‐4‐4′‐diamine (TPD) was also introduced into the PCaNI matrix. Results showed that PCaNI exhibited high glass transition temperature (~260 °C) and high optical transparency in the visible region. The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) of PCaNI were measured as 5.6 and 2.2 eV, while the TPD‐doped PCaNI showed 5.7 eV (HOMO) and 2.6 eV (LUMO). The PCaNI/silica hybrid nanolayers showed excellent solvent resistance due to the formation of covalent bonds between ITO and PCaNI. The HOLEDs with PCaNI/TPD or PCaSi/TPD hybrid nanolayers exhibited relatively higher luminance (~10,000 cd/m2), lower operating voltage (~6.5 V at 300 cd/m2), and higher current efficiency (~2.7 cd/A). © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2010  相似文献   

6.
A novel oligothiophene derivative containing the triphenylamine moiety with high glass transition temperature (Tg; 135 °C), 5,5′‐{bis[4‐di(4‐thiophenyl)amino]phenyl}‐2,2′‐bithiophene (TTPA‐dimer) was synthesized by the dimerization of tris[4‐(2‐thienyl)phenyl]amine (TTPA) with a palladium catalysis. Some types of electroluminescent (EL) devices that use the amorphous material for a hole‐ and an electron‐transporting with an emitting layer were fabricated. These devices emitted a bright green‐yellowish light (λemi; around 510 nm) with a small full width at half maximum (FWHM) rather than that of Alq3. The single layer EL device showed a maximum luminance of 221 cd/m2 at 8 V (0.06 lm/W at 100 cd/m2). On the other hand, the double layer (TTPA‐dimer/Alq3) EL device that used Alq3 as the electron transport material was increased up to 10830 cd/m2 at 12 V (0.89 lm/W at 300 cd/m2) and with a lower turn‐on voltage (3.2 V at 0.1 cd/m2) than other types of EL devices. Copyright © 2003 John Wiley & Sons, Ltd.  相似文献   

7.
8.
Fabrication of polymer light‐emitting diodes based on emission from the phosphorescent molecule fac‐tris(2‐phenylpyridine) iridium doped into a poly(N‐vinyl carbazole) host are reported. For single‐layered devices with magnesium‐silver cathodes, the luminance efficiency at 20 mA/cm2 was measured as 8.7 cd/A. This efficiency could be increased by over a factor of two by incorporation of evaporated small‐molecule layers into the device structure. Significant increases in device efficiency were also obtained without these evaporated layers by modification of the electrodes. Incorporation of 3,4‐poly(ethylene dioxythiophene):poly(styrene sulfonate) at the anode improved the device efficiency but had little impact on drive voltage. Insertion of lithium fluoride at the cathode resulted in no improvement in performance for magnesium‐silver and aluminum cathodes, but a significant improvement was realized in efficiency and drive voltage for calcium‐aluminum cathodes. Excellent device performance was observed for all three cathode metals used in conjunction with cesium fluoride. Through optimization of the electrodes and emitter‐layer thickness, devices exhibiting efficiencies as high as 37.3 cd/A are realized. © 2003 Wiley Periodicals, Inc. J Polym Sci Part B: Polym Phys 41: 2715–2725, 2003  相似文献   

9.
Summary: Modern multilayer organic light‐emitting devices (OLED) are fabricated easily and at low cost by spin‐coating with subsequent crosslinking of the layers. For this purpose, a low‐molecular‐weight hole‐transport material based on triphenyl amines bearing crosslinkable oxetane groups was synthesized. Crosslinking of the spin‐coated layer was initiated with UV irradiation using an iodonium‐salt photoinitiator and was observed using realtime FT‐IR spectroscopy. Standard photolithography techniques can be used for structuring the material on the micrometre scale.

An AFM image of the photopatterned bis‐oxetane‐functionalized low‐molecular‐weight hole‐transport material based on triphenyl amines synthesized here.  相似文献   


10.
We describe a facile fabrication of white light‐emitting cadmium sulfide (CdS)‐poly(HEA‐co‐NVK) nanocomposites [2‐hydroxyethyl acrylate (HEA) and N‐vinylcarbazole (NVK)] via plasma‐ignited frontal polymerization (PIFP), a novel and rapid reaction mode of converting monomers into polymers in minutes. Frontal polymerization was initiated by igniting the upper side of the reactant with plasma. Once initiated, no additional energy was required for the polymerization to occur. The chemical functional groups of the as‐prepared nanocomposites were thoroughly investigated using Fourier transform infrared spectra. The dependence of the front velocity and front temperature on the initiator concentration and weight ratios of HEA/NVK was also investigated in detail. Perhaps more interestingly, the white light‐emitting materials synthesized by ingeniously incorporating the compensating colors of yellow emitting from 3‐(trimethoxysilyl)‐1‐propanethiol‐capped CdS nanocrystals and blue emitting from carbazole‐containing polymer were conveniently applied onto a commercial UV light‐emitting diode (LED) to generate white LEDs. The subtle change in the weight ratios of CdS/NVK can significantly impact the color hue. The white light becomes gradually colder with the increase of NVK, but becomes gradually warmer with the increase concentration of CdS nanocrystals. In a broad perspective, these white light‐emitting materials designed by PIFP approach will open a new pathway to develop “QD‐polymer nanocomposite down‐conversion LED” in a fast and efficient way. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012  相似文献   

11.
Two novel organic–inorganic hybrid polyfluorene derivatives, poly{(9,9′‐dioctyl‐2,7‐fluorene)‐co‐(9,9′‐di‐POSS‐2,7‐fluorene)‐co‐[2,5‐bis(octyloxy)‐1,4‐phenylene]} (PFDOPPOSS) and poly{(9,9′‐dioctyl‐2,7‐fluorene)‐co‐(9,9′‐di‐POSS‐2,7‐fluorene)‐co‐bithiophene} (PFT2POSS), were synthesized by the Pd‐catalyzed Suzuki reaction of polyhedral oligomeric silsesquioxane (POSS) appended fluorene, dioctyl phenylene, and bithiophene moieties. The synthesized polymers were characterized with 1H NMR spectroscopy and elemental analysis. Photoluminescence (PL) studies showed that the incorporation of the POSS pendant into the polyfluorene derivatives significantly enhanced the fluorescence quantum yields of the polymer films, likely via a reduction in the degree of interchain interaction as well as keto formation. Additionally, the blue‐light‐emitting polyfluorene derivative PFDOPPOSS showed high thermal color stability in PL. Moreover, single‐layer light‐emitting diode devices of an indium tin oxide/poly(3,4‐ethylene dioxythiophene):poly(styrene sulfonate)/polymer/Ca/Al configuration fabricated with PFDOPPOSS and PFT2POSS showed much improved brightness, maximum luminescence intensity, and quantum efficiency in comparison with devices fabricated with the corresponding pristine polymers PFDOP and PFT2. In particular, the maximum external quantum efficiency of PFT2POSS was 0.13%, which was twice that of PFT2 (0.06%), and the maximum current efficiency of PFT2POSS was 0.38 cd/A, which again was twice that of PFT2 (0.19 cd/A). © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 2943–2954, 2006  相似文献   

12.
Rigid polymer backbones have often been considered to be detrimental to the packing of mesogenic pendants, and polyacetylenes have generally been regarded as unpromising materials for light‐emitting applications. Our group, however, has succeeded in creating a series of liquid‐crystalline polyacetylenes with rigid backbones and a variety of light‐emitting polyacetylenes with luminescent chromophores. Here we demonstrate that the rigid polyacetylene skeleton can play a constructive role in guiding the alignments of mesogenic pendants and prove that polyacetylenes can be highly emissive with photoluminescence quantum yields of up to 98% and electroluminescence performances comparable or superior to those of the best blue‐light‐emitting polymers. © 2003 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 41: 2607–2629, 2003  相似文献   

13.
A series of novel styrene derived monomers with triphenylamine‐based units, and their polymers have been synthesized and compared with the well‐known structure of polymer of N,N′‐bis(3‐methylphenyl)‐N,N′‐diphenylbenzidine with respect to their hole‐transporting behavior in phosphorescent polymer light‐emitting diodes (PLEDs). A vinyltriphenylamine structure was selected as a basic unit, functionalized at the para positions with the following side groups: diphenylamine, 3‐methylphenyl‐aniline, 1‐ and 2‐naphthylamine, carbazole, and phenothiazine. The polymers are used in PLEDs as host polymers for blend systems with the following device configuration: glass/indium–tin–oxide/PEDOT:PSS/polymer‐blend/CsF/Ca/Ag. In addition to the hole‐transporting host polymer, the polymer blend includes a phosphorescent dopant [Ir(Me‐ppy)3] and an electron‐transporting molecule (2‐(4‐biphenyl)‐5‐(4‐tert‐butylphenyl)‐1,3,4‐oxadiazole). We demonstrate that two polymers are excellent hole‐transporting matrix materials for these blend systems because of their good overall electroluminescent performances and their comparatively high glass transition temperatures. For the carbazole‐substituted polymer (Tg = 246 °C), a luminous efficiency of 35 cd A?1 and a brightness of 6700 cd m?2 at 10 V is accessible. The phenothiazine‐functionalized polymer (Tg = 220 °C) shows nearly the same outstanding PLED behavior. Hence, both these polymers outperform the well‐known polymer of N,N′‐bis(3‐methylphenyl)‐N,N′‐diphenylbenzidine, showing only a luminous efficiency of 7.9 cd A?1 and a brightness of 2500 cd m?2 (10 V). © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 3417–3430, 2010  相似文献   

14.
A comprehensive numerical device simulation of the electrical and optical characteristics accompanied with experimental measurements of a new highly efficient system for polymer‐based light‐emitting diodes doped with phosphorescent dyes is presented. The system under investigation comprises an electron transporter attached to a polymer backbone blended with an electronically inert small molecule and an iridium‐based green phosphorescent dye which serves as both emitter and hole transporter. The device simulation combines an electrical and an optical model. Based on the known highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) levels of all components as well as the measured electrical and optical characteristics of the devices, we model the emissive layer as an effective medium using the dye's HOMO as hole transport level and the polymer LUMO as electron transport level. By fine‐tuning the injection barriers at the electron and hole‐injecting contact, respectively, in simulated devices, unipolar device characteristics were fitted to the experimental data. Simulations using the so‐obtained set of parameters yielded very good agreement to the measured current–voltage, luminance–voltage characteristics, and the emission profile of entire bipolar light‐emitting diodes, without additional fitting parameters. The simulation was used to gain insight into the physical processes and the mechanisms governing the efficiency of the organic light‐emitting diode, including the position and extent of the recombination zone, carrier concentration profiles, and field distribution inside the device. The simulations show that the device is severely limited by hole injection, and that a reduction of the hole‐injection barrier would improve the device efficiency by almost 50%. © 2012 Wiley Periodicals, Inc. J Polym Sci Part B: Polym Phys, 2012  相似文献   

15.
A new aromatic host polymer poly{[1,4‐bis(9‐decylcarbazole‐3‐yl)‐2,3,5,6‐tetrafluorobenzene‐3,3′‐diyl]‐alt‐[N‐methylisatin‐2‐one‐3,3‐diyl]} (PICzFB) containing carbazole–tetrafluorinebeneze–carbazole moiety in the π‐conjugated interrupted polymer backbone was synthesized by superacid‐catalyzed metal‐free polyhydroxyalkylation. The resulted copolymer PICzFB showed a comparatively wide band gap up to 3.32 eV and high triplet energy (ET) of 2.73 eV due to confined conjugation by the δ? C bond interrupted polymer backbone. Blue and green light‐emitting devices with PICzFB as host, FIrpic and Ir(mppy)3 as phosphorescent dopants showed the maximum luminous efficiencies of 5.0 and 27.6 cd/A, respectively. The results suggested that the strategy of incorporating bipolar unit into the π‐conjugated interrupted polymer backbone can be a promising approach to obtain host polymer with high triplet level for solution‐processed blue and green phosphorescent polymer light‐emitting diodes. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014 , 52, 1037–1046  相似文献   

16.
A new series of highly phenyl‐substituted polyfluorene derivatives were synthesized and characterized. The resulting polymers were amorphous and showed excellent solubility in common organic solvents, such as chloroform, tetrahydrofuran, xylene, toluene, chlorobenzene, and so forth. All possessed satisfied thermal stability with glass‐transition temperatures (Tg's) in the range of 79–115 °C. They emitted blue light with photoluminescent (PL) maximum peaks at about 408–412 nm in thin films. The PL efficiencies of the polymer films were measured around 30–33%. The highly phenylated pendants improved the Tg of polyfluorene without forming defects in the polymers and reduced their tendency to form aggregate/excimers. Polymer light‐emitting diodes were fabricated from these polymers with the configuration of indium tin oxide/polyethylenedioxythiophene:polystyrene sulfonic acid/polymer/Ba/Al, which emitted bright blue light with maximum peaks at 418–420 nm. The maximum external quantum efficiencies of these devices were 0.41–0.6%. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 2985–2993, 2004  相似文献   

17.
Substituent‐induced electroluminescence polymers—poly[2‐(2‐dimethyldodecylsilylphenyl)‐1,4‐phenylenevinylene] [(o‐R3Si)PhPPV], poly[2‐(3‐dimethyldodecylsilylphenyl)‐1,4‐phenylenevinylene] [(m‐R3Si)PhPPV], and poly[2‐(4‐dimethyldodecylsilylphenyl)‐1,4‐phenylenevinylene] [(p‐R3Si)PhPPV]—were synthesized according to the Gilch polymerization method. The band gap and spectroscopic data were tuned by the dimethyldodecylsilyl substituent being changed from the ortho position to the para position in the phenyl side group along the polymer backbone. The weight‐average molecular weights and polydispersities were 8.0–96 × 104 and 3.0–3.4, respectively. The maximum photoluminescence wavelengths for (o‐R3Si)PhPPV, (m‐R3Si)PhPPV, and (p‐R3Si)PhPPV appeared around 500–530 nm in the green emission region. Double‐layer light‐emitting diodes with an indium tin oxide/poly(3,4‐ethylenedioxythiophene)/polymer/Al configuration were fabricated with these polymers. The turn‐on voltages and the maximum brightness of (o‐R3Si)PhPPV, (m‐R3Si)PhPPV, and (p‐R3Si)PhPPV were 6.5–8.7 V and 1986–5895 cd/m2, respectively. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 2347–2355, 2004  相似文献   

18.
A conjugated poly(p‐CN‐phenylenevinylene) (PCNPV) containing both electron‐donating triphenylamine units and electron‐withdrawing cyano groups was prepared via Knoevenagel condensation in a good yield. Gel permeation chromatography suggested that the soluble polymer had a very high weight‐average molecular weight of 309,000. A bright and saturated red emission was observed under UV excitation in solution and film. Cyclic voltammetry showed that the polymer presented quasi‐reversible oxidation with a relatively low potential because of the triphenylamine unit. A single‐layer indium tin oxide/PCNPV/Mg–Ag device emitted a bright red light (633 nm). © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 3947–3953, 2004  相似文献   

19.
Two series of highly soluble novel nitrogen‐ and sulfur‐containing conjugated polymers were synthesized via an acid‐induced self‐polycondensation of functional monomers with methyl sulfinyl and aromatic groups. The well‐defined structures of synthesized polymers were confirmed by their NMR and IR spectra. The highest occupied molecular orbital energy values for these materials, estimated by cyclic voltammetry, showed a broad range of values from about 5.0 to 5.2 eV used as hole‐transport layers (HTL) in two‐layer light‐emitting diodes ITO/HTL/Alq3/Mg:Ag [ITO = indium tin oxide, and Alq3 = tris(8‐quinolinato) aluminum]. The typical turn‐on voltage of these diodes was about 4–5 V. The maximum brightness of the device was about 3440 cd/m2 at 20 V. The maximum efficiency was estimated to be 0.15 lm/W at 10 V. © 2002 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 40: 1321–1333, 2002  相似文献   

20.
Polyfluorene homopolymer ( P1 ) and its carbazole derivatives ( P2 – P4 ) have been prepared with good yield by Suzuki coupling polymerization. P2 is an alternating copolymer based on fluorene and carbazole; P3 is a hyperbranched polymer with carbazole derivative as the core and polyfluorene as the long arms; P4 is a hyperbranched polymer with carbazole derivative as the core and the alternating fluorene and carbazole as the long arms. These polymers show highly thermal stability, and their structures and physical properties are studied using gel permeation chromatography, 1H NMR, 13C NMR, elemental analysis, Fourier transform infrared spectroscopy, thermogravimetry, UV–vis absorption, photoluminescence, and cyclic voltammetry (CV). The influence of the incorporation of carbazole and the hyperbranched structures on the thermal, electrochemical, and electroluminescent properties has been investigated. Both carbazole addition and the hyperbranched structure increase the thermal and photoluminescent stability. The CV shows an increase of the HOMO energy levels for the derivatives, compared with polyfluorene homopolymer ( P1 ). The EL devices fabricated by these polymers exhibit pure blue‐light‐emitting with negligible low‐energy emission bands, indicating that the hyperbranched structure has a strong effect on the PLED characteristics. The results imply that incorporating carbazole into polyfluorene to form a hyperbranched structure is an efficient way to obtain highly stable blue‐light‐emitting conjugated polymers, and it is possible to adjust the property of light‐emitting polymers by the amount of carbazole derivative incorporated into the polymers. © 2007 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 790–802, 2008  相似文献   

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