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1.
Two luminescent materials based on indolo[3,2-b]carbazole have been designed and synthesized. They were highly fluorescent both in solution and in the solid state. High-performance electroluminescent devices with indolo[3,2-b]carbazole luminescent derivatives as the emissive materials were fabricated for the first time with low turn-on voltage of 2.65 V, high luminescence efficiency of 7.92 lm W?1, and high brightness of 68729 cd m?2. The results demonstrated that indolo[3,2-b]carbazole has great potentials as promising building block for highly efficient electroluminescent materials.  相似文献   

2.
A novel indolo[3,2-b]carbazole derivative containing B(Mes)2 groups, 5,11-dibutyl-2,8-bis(dimesitylboryl) indolo[3,2-b]carbazole (DBDMBICZ), was synthesized and structurally characterized by elemental analysis, NMR, MS. The thermal, electrochemical and photophysical properties of DBDMBICZ were characterized by thermogravimetric analysis, electrochemical methods, UV–vis absorption spectroscopy and fluorescence spectroscopy. DBDMBICZ exhibited high fluorescence quantum yields (Φmax = 0.76) in solution and excellent thermal stability (Td = 290 °C, Tg = 170 °C) and electrochemical stability. The multi-layered OLEDs devices with the configuration of ITO/NPB/CBP/light-emitting layer/Bphen/LiF/Al are fabricated by using DBDMBICZ as light-emitting layer. The devices show the same pure blue emissions at different voltages and relative good electroluminescent performances. The results indicate that DBDMBICZ has potential applications as an excellent optoelectronic material in optical field.  相似文献   

3.
Three 2,2-dicyanovinyl (DCV) end-capped A-π-D-π-A type oligothiophenes (DCV-OTs) containing dithieno[3,2-b:2′,3′-d]silole (DTSi), cyclopenta[1,2-b:3,4-b′]dithiophene (DTCP) or dithieno[3,2-b:2′,3′-d]pyrrole (DTPy) unit as the central donor part, mono-thiophene as the π-conjugation bridge were synthesized. The absorption spectroscopies, cyclic voltammetry of these compounds were characterized. Results showed that all these compounds have intensive absorption band over 500–680 nm with a LUMO energy level around −3.80 eV, which is slightly higher than that of [6,6]phenyl-C61-butyric acid methyl ester (PC61BM, ELUMO = −4.01 eV), but lower than that of poly(3-hexylthiophene) (P3HT, ELUMO = −2.91 eV). Solution processed bulk heterojunction “all-thiophene” solar cells using P3HT as electron donor and the above mentioned oligothiophenes as electron acceptor were fabricated and tested. The highest power conversion efficiency (PCE) of 1.31% was achieved for DTSi-cored compound DTSi(THDCV)2, whereas PTB7:DTSi(THDCV)2 based device showed slightly higher PCE of 1.56%. Electron mobilities of these three compounds were measured to be around 10−5 cm2 V−1 s−1 by space charge limited current method, which is much lower than that of PC61BM, and was considered as one of the reason for the low photovoltaic performance.  相似文献   

4.
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.  相似文献   

5.
We synthesized solution-processable iridium complexes having bulky carbazole dendrons, fac-tris[2-{3-(3,5-bis(3,6-di-n-butylcarbazol-9-yl)phenyl)Phenyl)pyridine]iridium (III) (mCP)3Ir and fac-bis[2-{3-(3,5-bis(3,6-di-n-butylcarbazol-9-yl)phenyl)phenyl}pyridine][2-{3-(3,5-di(4-pyridyl)phenyl)phenyl}pyridine]iridium (III) (mCP)2(bpp)Ir. Photoluminescence quantum efficiencies (PLQEs) of (mCP)3Ir and (mCP)2(bpp)Ir in their diluted solutions were 91% and 84%, respectively. They showed high PLQEs of 49% for (mCP)3Ir and 29% for (mCP)2(bpp)Ir even in a neat film. The triplet exciton energy level of the dendronized ligand (2.8 eV), 2-[3-{3,5-bis(3,6-di-n-butylcarbazol-9-yl)phenyl}]pyridine 10, and the dendron (2.9 eV), 3,5-bis(3,6-di-n-butylcarbazol-9-yl)benzene 7, are enough higher than that of the core complex Ir(ppy)3 (2.6 eV). External quantum efficiency (EQE) of single layer light-emitting device with (mCP)2(bpp)Ir was much higher than that of (mCP)3Ir because of better affinity of (mCP)2(bpp)Ir to cathode metal. When an electron transporting and hole-blocking material was used, the EQEs of double layer devices were dramatically improved to 8.3% for (mCP)3Ir and 5.4% for (mCP)2(bpp)Ir at 100 cd/m2.  相似文献   

6.
《Organic Electronics》2014,15(6):1184-1188
Single-crystalline organic transistors of 3,11-didecyl-dinaphtho[2,3-d:2′,3′-d′]benzo[1,2-b:4,5-b′]dithiophene (C10-DNBDT-NW) and 2,9-didecyl-dinaphtho[2,3-b:2′,3′-f]thieno[3,2-b]thiophene (C10-DNTT) were fabricated by solution processes on top of the patterned hybrid ultrathin gate dielectrics consisting of 3.6 nm-thick aluminum oxide and self-assembled monolayers (SAMs). Due to the excellent crystallinity of the channel films, bottom-gate and top-contact field-effect transistors exhibited the average field-effect mobility of 3.7 cm2/V s and 4.3 cm2/V s for C10-DNBDT-NW and C10-DNTT, respectively. These are the first successful devices of solution-processed single-crystalline transistors on ultrathin gate dielectrics with the mobility above 1 cm2/V s, opening the way to develop low-power-consumption and high-performance printed circuits.  相似文献   

7.
Three new metal-free organic dyes FD13 with a planar dithieno[3,2-b:2′,3′-d]pyrrole unit as linker were synthesized and used for dye-sensitized solar cells with high molar extinction coefficients. In this work, dithieno[3,2-b:2′,3′-d]pyrrole was employed as π-conjugated bridge to construct A–π–d–π–A organic dyes, where 9,9-dihexyl-9H-fluorene was used as a donor, and cyanoacrylic acid as an electron acceptor. For a typical device, a solar energy conversion efficiency (η) of 6.36% based on FD2 was achieved under simulated AM 1.5 solar irradiation (100 mW cm?2) with a short-circuit photocurrent density (Jsc) of 13.76 mA cm?2, an open-circuit voltage (Voc) of 669 mV, a fill factor (ff) of 0.691. The results suggest that the organic dye with a functionalized dithienopyrrole unit is a promising candidate for DSSCs due to its high molar extinction coefficients.  相似文献   

8.
The photophysical and electrical properties of copolymers based on 2,6-polyphenylquinolines containing a bridging oxygen or phenylamine group between quinoline rings and octyl- or dodecylcarbazole or dioctylindolo[3,2-b]carbazole fragments in the aromatic radical are studied. It is shown that the introduction of carbazole and indolo[3,2-b]carbazole fragments emitting in the visible spectral range into the aromatic radical of a copolymer makes it possible to obtain white luminescence. The intensity of this luminescence exceeds, for copolymers in a photoinert matrix, that of the initial homopolymers. This circumstance, combined with rather high carrier mobilities on the order of 5 × 10?6 cm2 V?1 s?1, makes the copolymers promising for the development of electroluminescent devices on their basis.  相似文献   

9.
Efficient deep-blue fluorescent emitters are of particular significance in organic light-emitting devices (OLEDs). An ambipolar deep-blue emitter, 4,4′-bis(4-(1-(4-(tert-butyl)phenyl)-1H-phenanthro[9,10-d]imidazol-2-yl)phenyl)-1,1′-binaphthalene (2NBTPI), was designed, synthesized and applied in a high-efficiency deep-blue emitting OLED. By modifying with binaphthyl, 2NBTPI exhibits a high thermal stability, deep blue emission as well as spatially separated HOMO and LUMO orbits. Comparing with its mononaphthyl counterpart 1,4-bis(4-(1-(4-(tert-butyl)phenyl)-1H-phenanthro[9,10-d]imidazol-2-yl)phenyl)naphthalene (NBTPI), 2NBTPI shows more balanced charge transport properties, better color purity (color index: (0.15, 0.09) versus (0.15, 0.11)), higher external quantum efficiency (EQE) (5.95% versus 5.73%) and slower efficiency roll-off (EQE roll-off at 100 mA cm−2: 13.1% versus 27.6%). To the best of our knowledge, OLED performances of 2NBTPI are comparable to the best reported non-doped deep-blue emitters.  相似文献   

10.
Charge mobility characteristics of a newly synthesised 2,6-bis[2-(9,9-dihexyl-9H-fluorene)]-N-(4-hexylphenyl)-dithieno[3,2-b:2′,3′-d]pyrrole oligomer (DTP-FLU) was studied as a function of electric field and temperature using time-of-flight photoconductivity measurement. It is found that the DTP-FLU oligomer is a hole transporting material with a hole mobility of 7.7 × 10?6 cm2/Vs at an applied electric field of 2.9 × 105 V/cm at 298 K. The dependence of hole mobility with applied electric field and temperature is studied in detail by analyzing the experimental results using the Bassler’s Gaussian disorder model and Correlated disorder model. The energetic disorder parameter (σ) = 100 meV, mobility pre-factor (μ) = 6.1 × 10?4 cm2/Vs and positional disorder parameter (Σ) = 2.4 were extracted using Gaussian disorder model. The film morphology and photophysical properties of this new oligomer are also studied in detail.  相似文献   

11.
A series of derivatives based on annelated β-oligothiophenes were synthesized and characterized as active layer in organic field-effect transistors (OFETs). Highest field-effect mobility of 0.52 V?1 s?1 for 2,5-dibiphenyl-dithieno[2,3-b:3′,2′-d]thiophene (DBP-DTT), 2.2 cm2 V?1 s?1 for 2,5-distyryl-dithieno[2,3-b:3′,2′-d]thiophene (DEP-DTT), and 0.16 cm2 V?1 s?1 for 1,4-di[2-dithieno[2,3-b:3′,2′-d] thiophen-2-yl-vinyl]benzene (DDTT-EP) were obtained, while 2,5-diphenyl-dithieno [2,3-b:3′,2′-d]thiophene (DP-DTT) presents no field-effect behaviors. Their thermal, optical and electrochemical properties, topographical and X-ray diffraction patterns of films, and the single crystal structures were also investigated. With the end-capping groups changing in these materials, the intermolecular interactions could transform from S–S in DP-DTT to S–C in DBP-DTT, to S–π in DEP-DTT, and to the coexisting of S–S and S–π in DDTT-EP. According to the device performances and the results of transfer integral calculations, it was revealed that S–π intermolecular interaction benefits not only improving the mobility but also reducing the threshold voltage (VT), while S–S intermolecular interaction is not favorable for promoting the mobility.  相似文献   

12.
In this study, we synthesized three anthracene derivatives featuring carbazole moieties as side groups - 2-tert-butyl-9,10-bis[4-(9-carbazolyl)phenyl]anthracene (Cz9PhAnt), 2-tert-butyl-9,10-bis{4-[3,6-di-tert-butyl-(9-carbazolyl)]phenyl}anthracene (tCz9PhAnt), and 2-tert-butyl-9,10-bis{4′-[3,6-di-tert-butyl-(9-carbazolyl)]biphenyl-4-yl}anthracene (tCz9Ph2Ant) - for use in blue organic light emitting devices (OLEDs). The anthracene derivatives presenting rigid and bulky tert-butyl-substituted carbazole units possessed high glass-transition temperatures (220 °C). Moreover, the three anthracene derivatives exhibited strong blue emissions in solution, with high quantum efficiencies (91%). We studied the electroluminescence (EL) properties of non-doped OLEDs incorporating these anthracene derivatives, with and without a hole-transporting layer (HTL). OLEDs incorporating an HTL provided superior EL performance than did those lacking the HTL. The highest brightness (6821 cd/m2) was that for the tCz9PhAnt-based device; the greatest current efficiency (2.1 cd/A) was that for the tCz9Ph2Ant-based device. The devices based on these carbazole-substituted anthracene derivatives also exhibited high color purity.  相似文献   

13.
The synthesis and properties of a glass-forming carbazole compound 9-(ethyl)-3,6-bis(4,4′-dimethoxydiphenylaminyl)-carbazole are reported. The thermal, optical and electrochemical properties of the hole-transporting molecule were studied by differential scanning calorimetry, thermogravimetric analysis, UV/Vis spectroscopy and cyclic voltammetry. The molecular glass exhibits a thermal stability as high as 370 °C and a glass transition temperature of 68 °C. The synthesized coumpound absorbs in the 250–400 nm range and possesses an optical band gap of 2.76 eV, avoiding any screening effect with the dye. The solid state ionization potential (IPss) of the molecule, estimated by cyclic voltammetry is around 4.77 eV, higher than the standard spiro-OMeTAD hole-transporting material. The compound was finally assessed as hole-transporting material in the solid state dye-sensitized solar cells with (5-(1,2,3,3 a,4,8b-hexahydro-4-[4-(2,2-diphenylvinyl)phenyl]-cyclopenta[b]indole-7-ylmethylene)-4-oxo-2-thioxo-thiazolidin-3-yl)acetic acid (D102) as sensitizer. The effect of the purity of the glassy molecule on photovoltaic performances is discussed and showed a two-fold increase of the power conversion efficiency after purification by sublimation, going from 0.82% to 1.62% under standard AM 1.5 G solar irradiation (100 mW/cm2).  相似文献   

14.
Four new host/hole-transporting materials, namely 4,4′,4″,4‴-(adamantane-1,3,5,7-tetrayl)tetrakis(N,N-diphenylaniline) (4TPA-Ad, 1),4,4′,4″,4‴-(adamantane-1,3,5,7-tetrayl)tetrakis(N,N-di-p-tolylaniline) (4MTPA-Ad, 2), 1,3,5,7-tetrakis(4-(9H-carbazol-9-yl)phenyl)adamantane (4Cz-Ad, 3) and 1,3,5,7-tetrakis(4-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)adamantane (4tBuCz-Ad, 4), were designed and synthesized by incorporating four electron-donating arylamine units into the rigid adamantane skeleton via a simple C–N coupling reaction. Their thermal, photophysical and electrochemical properties were investigated. The molecular design endows the materials with high triplet energies of ∼3.0 eV, good solution processability, high thermal stability and appropriate HOMO levels. Two types of electroluminescent devices using 14 as hole-transporting or host materials were fabricated. The device based on 2 as solution-processed hole-transporting material and tris(quinolin-8-yloxy)aluminum as an emitter revealed a maximum current efficiency of 4.2 cd A−1, which was comparable with the TAPC-based control device. The sky-blue device employing 2 as solution-processed host material and 4,6-(difluorophenyl)pyridine-N,C2′)picolinate (FIrpic) as an emitter showed a maximum current efficiency of 16.6 cd A−1 with Commission Internationale de I’Eclairage (CIE) coordinates of (0.16, 0.32).  相似文献   

15.
We fabricated organic thin film transistors (OTFTs) using soluble 5,5′-(2,6-Bis((4-hexylphenyl)ethynyl)anthracene-9,10-diyl)bis(ethyne-2,1-diyl)bis(2-hexylthieno[3,2-b]thiophene (HTT-ant-THB) as an active layer. We studied the photo-responsive and the gate field-dependent charge transport characteristics of the HTT-ant-THB-based OTFTs. When light (λex = 505 nm) was irradiated on the OTFTs, negative differential resistance (NDR) behavior (i.e., negative slope of the current versus voltage curve) was observed in the reverse bias region of the source-drain current versus voltage characteristics. The NDR effect observed in this study is unique and is controlled by the wavelength and power of the incident light. The current hysteresis and NDR characteristics can be explained in terms of the trapping and releasing mechanism of the mobile charges at the interface between the electrodes and the organic layer. In addition, the NDR effect in the device disappeared on applying negative gate bias.  相似文献   

16.
A facile strategy for the introduction of tert-butyl and hexyl chains to the indolo[3,2,1-jk]carbazole scaffold is presented. With these building blocks six materials based on three different 4,4′-bis(N-carbazolyl)-1,1-biphenyl derivatives with varying degree of planarization were prepared. Characterization of the materials showed that the alkyl chains have only minor effects on the photophysical properties of the compounds. In contrast, thermal robustness towards decomposition and electrochemical stability are increased by the introduced alkyl chains. Detailed investigation of the solubility in five different solvents revealed that the incorporation of the alkyl chains increases the solubility significantly. The increased solubility of the materials allowed the application as host materials in red, green and sky-blue solution processed phosphorescent organic light emitting diodes. Hence, this work presents the first solution processed light emitting devices based on the indolo[3,2,1-jk]carbazole scaffold.  相似文献   

17.
We report on a new p-type organic semiconductor single crystal, 5,10,15-trimethyl-10,15-dihydro-5H-diindolo[3,2-a:3’,2’-c]carbazole (N-trimethyltriindole). This molecule crystallizes forming a highly ordered columnar structure in which stacked molecules are situated at two alternating distances (3.53 Å and 3.68 Å) along the column as determined by single crystal X-ray diffraction analysis. These short intermolecular distances between adjacent units, make this system an ideal candidate for charge-transport processes along the stacks.Relevant parameters for transport (i.e. internal reorganization energies, transfer integral) have been estimated by DFT calculations at a 6-311G(d,p)/B3LYP level of theory. As a double check for the transfer integral, the electronic band structure of a one-dimensional stack of molecules has been computed. The electronic properties of this material have been studied both theoretically and experimentally. Its HOMO value is found to coincide with Au work function (ΦAu = 5.1 eV), thus low barriers are expected for hole injection from gold electrodes. The hole mobility of this material has been predicted theoretically considering a hopping-type mechanism for the charge-transport and determined experimentally at the space charge limited current (SCLC) regime of the current–voltage measurements. Both theoretical and experimental values are in good agreement. The high hole mobility (μmin = 0.4 cm2 V?1 s?1) of this material points towards its useful application in the organic electronics arena. N-Trimethyltriindole single crystals constitute an essential model to study transport properties of triindole-based materials and to design new derivatives with improved electronic performance.  相似文献   

18.
Two new conjugated D–A polymers P3 (PBTT-d-BTT) and P4 (PBTT-d-TPD) based on same benzo[1,2-b:3,4-b′:6,5-b″] trithiophene (BTT) donor and different acceptors monomers 5,8-dibromo-2-dodecanoylbenzo[1,2-b:3,4-b′:6,5-b″] trithiophene (d-BTT), and 1,3-dibromo-5-(2-ethylhexyl)thieno[3,4]pyrrol-4,6-dione (d-TPD) respectively, were synthesized by Stille cross-coupling reaction and characterized by gel permeation chromatography (GPC), 1H NMR, UV–Vis absorption, thermal analysis and electrochemical cyclic voltammetry (CV) tests. Photovoltaic properties of the polymers were studied by using the polymers as donor and PC71BM as acceptor with a weight ratio of polymer:PC71BM 1:1, 1:2 and 1:2.5. The optimized photovoltaic device was fabricated with an active layer of a blend P3:PC71BM and P4:PC71BM with a blend ratio of 1:2 showed PCE 3.16% and 2.42%, respectively under illumination of AM 1.5 at 100 mW/cm2 with solar simulator. The PCE of the device based on P3:PC71BM processed with DIO/o-DCB has been further improved up to 4.64% with Jsc of 10.52 mA/cm2 and FF of 0.58 attributed to the increase in crystalline nature of active layer and more balanced charge transport in the device, induced by DIO additive.  相似文献   

19.
There is an increasing need to develop stable, high-intensity, efficient OLEDs in the deep blue and UV. Applications include blue pixels for displays and tunable narrow solid-state UV sources for sensing, diagnostics, and development of a wide band spectrometer-on-a-chip. With the aim of developing such OLEDs we demonstrate an array of deep blue to near UV tunable microcavity (μc) OLEDs (λ ∼373–469 nm) using, in a unique approach, a mixed emitting layer (EML) of poly(N-vinyl carbazole) (PVK) and 4,4′-bis(9-carbazolyl)-biphenyl (CBP), whose ITO-based devices show a broad electroluminescence (EL) in the wavelength range of interest. This 373–469 nm band expands the 493–640 nm range previously attained with μcOLEDs into the desired deep blue-to-near UV range. Moreover, the current work highlights interesting characteristics of the complexity of mixed EML emission in combinatorial 2-d μcOLED arrays of the structure 40 nm Ag/x  nm MoOx/∼30 nm PVK:CBP (3:1 weight ratio)/y  nm 4,7-diphenyl-1,10-phenanthroline (BPhen)/1 nm LiF/100 nm Al, where x = 5, 10, 15, and 20 nm and y = 10, 15, 20, and 30 nm. In the short wavelength μc devices, only CBP emission was observed, while in the long wavelength μc devices the emission from both PVK and CBP was evident. To understand this behavior simulations based on the scattering matrix method, were performed. The source profile of the EML was extracted from the measured EL of ITO-based devices. The calculated μc spectra indeed indicated that in the thinner, short wavelength devices the emission is primarily from CBP; in the thicker devices both CBP and PVK contribute to the EL. This situation is due to the effect of the optical cavity length on the relative contributions of PVK and CBP EL through a change in the wavelength-dependent emission rate, which was not suggested previously. Structural analysis of the EML and the preceding MoOx layer complemented the data analysis.  相似文献   

20.
Photoconductivity and birefringence are two important factors that affect performances of photorefractive devices. Here, the optical properties of this composite based on copoly[6,6′-bis(9-(2-ethylhexyl)carbazole-3-yl)/thieno-(2,5-b)thiophenylidenevinylene] as photoconducting material, 2-[3-[(E)-2(piperidine)-1-ethenyl]-5,5-dimethyl]-2-cyclohexenyliden]malononitrile as nonlinear optical chromophore, butyl benzyl phthalate as plasticizer and C60 as photosensitizer, has been compared to those of the corresponding non-π-conjugated polymer composite. The 50-μm thick photorefractive composite showed a diffraction efficiency 37.2% at 50 V/μm, which corresponded to a Δn of 2.62 × 10?3. When we compare the speeds of the current and the non-conjugated analogue composites, the current composite has about a factor of seven larger speeds due to the π-conjugated polymer backbone. We also discuss and present simple explanation of the observed effect.  相似文献   

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