- Synthesis and properties of carbazole-containing poly(aryleneethynylenes) and poly(aryleneimines)
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Novel poly(aryleneethynylenes) and poly(aryleneimines) containing carbazole units in the main chain were synthesized by polycondensation of diethynylcarbazoles with dihaloarenes, or diformylcarbazole with phenylenediamines, and their general properties we
- Takihana, Yoshihiro,Shiotsuki, Masashi,Sanda, Fumio,Masuda, Toshio
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- Architectural design of new conjugated systems carrying donor-π-acceptor groups (carbazole-CF3): Characterizations, optical, photophysical properties and DSSC's applications
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In this study, two new organic dyes containing substituted N-octyl carbazole as electron donor and -CF3 units as electron acceptor group were designed and synthesized for ZnO-based dye sensitized solar cells (DSSCs). The synthesized carbazole derivatized compounds 3,6-bis(3,5-bis(trifluoromethyl)phenyl)-9-octyl-9H-carbazole (IVa) and 3,6-bis(4-(trifluoromethyl)phenyl)-9-octyl-9H-carbazole (IVb) were characterized by FT-IR, 1H NMR, 13C NMR, HMBC and CHN analyses. The spectroscopic (UV–Vis and FL) and thermal properties (TGA-DTA) of these compounds were also investigated. The produced (IVa and IVb) ZnO films were used as photoanodes in all DSSCs. Microwave-assisted hydrothermal method was used to synthesize ZnO nanopowders with different morphologies which are used as photoanodes in DSSCs. The structural and morphological properties of ZnO nanopowders were investigated using X-ray diffraction (XRD) and field emission scanning electron microscopy (FESEM). ZnO-DSSCs were produced through coating ZnO nanopowders on transparent conductive fluorine-doped tin oxide (FTO) coated glass substrate using the Doctor Blade method. Current-voltage measurements of all produced DSSCs were carried out under a solar simulator with AM 1.5 G filter having an irradiance of 100 mW/cm2. Solar cell performances of all DSSCs such as; open-circuit voltage (Voc), short circuit current (Jsc), fill factor (FF) and power conversion efficiency (PCE) were analyzed.
- Caglar, Mujdat,Caglar, Yasemin,Derince, Betul,Gorgun, Kamuran
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- Effect of mono- and di-anchoring dyes based on o,m-difluoro substituted phenylene spacer in liquid and solid state dye sensitized solar cells
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Novel mono- and di-anchoring organic dyes have been designed and synthesized with o,m-difluoro substituted phenylene spacer and were tested for DSSCs in presence of solid-state (SJE-4) as well as liquid (BMII) electrolytes. The new and simple structures o
- Raju, Telugu Bhim,Vaghasiya, Jayraj V.,Afroz, Mohammad Adil,Soni, Saurabh S.,Iyer, Parameswar Krishnan
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- Structural controlled pure metallo-triangular assembly through bisterpyridinyl Dibenzo[b,d]thiophene, Dibenzo[b,d]furan and Dibenzo[b,d]carbazole
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A novel family of metallocycles was constructed by a one-pot self-assembly of three analogous bis(terpyridine) ligand monomers L1-L3, having different bent angles, with metal ions (Zn2+ or Cd2+). The dibenzo[b,d]thiophene-containing ligand L3 assembled with the metal ions to form a single trimer, whereas the dibenzo[b,d]furan-containing ligand L2 and dibenzo[b,d]carbazole-containing ligand L1 formed a mixture of trimers and tetramers. Heteroatoms (N, O, S) significantly contributed to the molecular size of the assemblies, owing to the bent angle of the bis-terpyridines ligands.
- Liu, Qianqian,Yang, Xiaoyu,Wang, Meng,Liu, Die,Chen, Mingzhao,Wu, Tun,Jiang, Zhiyuan,Wang, Pingshan
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supporting information
p. 2400 - 2405
(2019/03/14)
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- Phenyl-bridged and carboxyl-terminated A1-pi-A-D-A-pi-A1 type BT derivative and preparation method thereof
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The invention discloses a phenyl-bridged and carboxyl-terminated A1-pi-A-D-A-pi-A1 type BT derivative and a preparation method thereof. The preparation method of the phenyl-bridged and carboxyl-terminated A1-pi-A-D-A-pi-A1 type BT derivative comprises the
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Paragraph 0064; 0067; 0069
(2018/10/02)
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- Dialkyl-substituted naphtho-dioxodibenzothiophene monomer and preparation method thereof and polymer containing dialkyl-substituted naphtho-dioxodibenzothiophene unit and application of polymer
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The invention discloses a dialkyl-substituted naphtho-dioxodibenzothiophene monomer and a preparation method thereof and a polymer containing a dialkyl-substituted naphtho-dioxodibenzothiophene unit and the application of the polymer. A high-absorption electron unit -SO2- exists in the dialkyl-substituted naphtho-dioxodibenzothiophene monomer, and thus the electron affinity of a molecule can be improved. Through introducing of an unsymmetrical substituting condensed ring structure and an alkyl group, the electron affinity of the monomer can be lowered, and meanwhile, solubleness of the monomer in organic solvent is improved greatly. The dialkyl-substituted naphtho-dioxodibenzothiophene monomer obtains a homopolymer or a copolymer containing the dialkyl-substituted naphtho-dioxodibenzothiophene unit through Suzuki or Stille or Yamamoto polymerization reaction, and the obtained polymer has good solubleness in the organic solvent, is suitable for solution processing, and has wide application prospects in preparation of electroluminescent devices, organic solar cells and organic field effect transistors.
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- Novel dual BODIPY-carbazole conjugates with various linkers
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Four dual BODIPY-carbazole conjugates (BDPa-d, BODIPY is 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene), with various π bridges, including none, phenyl, thiophene, and furan, were designed and synthesized. The results suggest that the π bridges have significant effect on the thermal, photophysical, and electrochemical properties of the conjugates. BDPc and BDPd, with a five-membered heterocycle as a π bridge possessing more coplanar molecular geometry, exhibit broader and red-shifted absorption with an obvious charge transfer shoulder peak, as well as red-shifted emission. UV-visible absorption spectroscopy and cyclic voltammetry results show that the extension of the π-conjugated system leads to a reduction in the optical gap with a decrease of the LUMO level. All conjugates display remarkable Stokes shifts (107-216 nm) and low fluorescence quantum yields. BDPc and BDPd, which essentially possess broad and intense absorption, and suitable HOMO-LUMO energy levels, are potential candidates for light-harvesting and photovoltaic applications.
- Zong, Qiao,Zhao, Hongbin,Zhou, Weinan,Zhang, Wentao,Liao, Junxu,Yang, Nianfa
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p. 806 - 815
(2017/07/07)
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- Synthesis and characterization of 1,3,5-triphenylamine derivatives with star-shaped architecture
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In this work we report the synthesis, electrochemical and optical properties of five new, star shaped compounds containing both carbazole and triphenylamine moieties, further endcapped with thiophene or 3,4-ethylenedioxythiophene units. Electrochemical, UV-visible spectroscopy and fluorescence methods were employed to study the properties of these compounds as well as their electropolymers. The basic characteristics such as the band gaps, HOMO and LUMO values, absorption and emission maximum wavelengths of the monomers and the polymers are reported and discussed.
- Brzeczek, Alina,Karon, Krzysztof,Higginbotham, Heather,J?drysiak, Rafa? G.,Lapkowski, Mieczyslaw,Walczak, Krzysztof,Golba, Sylwia
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- Carbazole/fluorene based conjugated small molecules: Synthesis and comparative studies on the optical, thermal and electrochemical properties
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A series of new molecular materials with varying carbazole and fluorene contents were prepared employing Suzuki coupling and their properties were compared. A variation of the core nucleus from fluorene to carbazole was a key point to study its effect on the thermal, optical and electrochemical properties. The materials were characterized by FTIR, 1H-, 13C-NMR, APCI-MS and elemental microanalyses. The synthesized materials exhibit slightly bathochromic shifted UV/Vis spectra in dilute solution and emission maxima in the blue region along with good thermal stability. The dyes with a fluorene core are electrochemically and spectrally stable with high lying HOMO levels, in contrast to the carbazole only materials, having potential as light emitting and hole transporting materials in organic light emitting diodes.
- Irfan, Madiha,Belfield, Kevin D.,Saeed, Aamer
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p. 48760 - 48768
(2015/06/16)
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- Ni(COD)2 coupling of 3,6-dibromocarbazoles as a route to all-carbazole shape persistent macrocycles
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The number of applications for carbon-based materials has experienced tremendous growth over the last decade arising from their low toxicity, straight-forward chemical modification, and interesting electronic properties. Among these materials, self-assembled structures based on shape persistent macrocycles are perhaps the most exciting as they offer a means to prepare a wide range of morphologies through reversible assembly of these molecular precursors. In this letter, we report on the preparation of a novel family of all-carbazole shape persistent macrocycles through the simple single-step reaction of the corresponding 3,6-dibromocarbazoles over Ni(COD)2. The resultant macrocycles display optical properties characteristic of the parent N-alkyl polycarbazoles, with quantum yields ranging from 11% up to 21% suggesting that certain substituents induce the formation of highly emissive aggregates, which could potentially provide a mechanism for the preparation of functional self-assembled nanomaterials.
- Coumont, Leah S.,Veinot, Jonathan G.C.
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supporting information
p. 5595 - 5598
(2015/09/21)
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- Boron ketoiminate-based conjugated polymers with tunable AIE behaviours and their applications for cell imaging
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Three new boron ketoiminate-based conjugated polymers P1, P2, and P3 were designed and synthesized through the Sonogashira coupling reaction of 4,6-bis(4-bromophenyl)-2,2-difluoro-3-phenyl-2H-1,3,2-oxazaborinin-3-ium-2-uide (M1) with 1,4-diethynyl-2,5-bis
- Dai, Chunhui,Yang, Dongliang,Zhang, Wenjie,Fu, Xiao,Chen, Qingmin,Zhu, Chengjian,Cheng, Yixiang,Wang, Lianhui
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supporting information
p. 7030 - 7036
(2015/09/07)
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- Influence of polyhedral oligomeric silsesquioxanes (POSS) on blue light-emitting materials for OLED
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By using Heck polycondensation, we have synthesized carbazole-based alt-copolymers tethered with polyhedral oligomeric silsesquioxanes (POSS), which had well-defined architectures, similar polymerization degrees and the different contents of POSS. The effect of POSS content and the length of the side chain containing POSS on the electroluminescence properties of these polymers were investigated. POSS particles in these alt-copolymers showed excellent dispersity and prevented the interchain aggregation of polymers in film state well. Besides, POSS benefited charge balance by increasing the electron current density, which led to a higher luminance and current efficiency, as well as purer blue light-emitting.
- Zhang, Tianfu,Wang, Jinze,Zhou, Manxi,Ma, Li,Yin, Guangzhong,Chen, Guangxin,Li, Qifang
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p. 2478 - 2486
(2014/04/03)
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- Synthesis and characterization of thermally crosslinkable hole-transporting polymers for PLEDs
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Two new thermally crosslinkable hole-transporting polymers, X-PTPA and X-PCz, were synthesized via Yamamoto coupling reactions. The number-averaged molecular weights (Mn) of X-PTPA and X-PCz were found to be 45,000 and 48,000, respectively, and therewith, polydispersity indices were of 1.8 and 1.7, respectively. Thermally crosslinked X-PTPA and X-PCz exhibit excellent solvent resistance and stable optoelectronic properties. The UV-visible maximum absorption peaks of X-PTPA and X-PCz in the thin film state are at 389 and 322 nm, respectively. The HOMO levels of X-PTPA and X-PCz are estimated to be -5.27 and -5.39 eV, respectively. Multilayered devices (ITO/crosslinked X-PTPA or X-PCz/SY-PPV/LiF/Al) were fabricated with SY (SuperYellow) as the emitting layer. The maximum efficiency of the multilayered device with a crosslinked X-PTPA layer is approximately three times higher than that of the device without a crosslinked X-PTPA layer and much higher than that of the crosslinked X-PCz device. This result can be explained by the observations that crosslinked X-PTPA produces increased electron accumulation within the emitter, SY, and also efficient exciton formation due to improved charge balance. Copyright
- Park, Sang-Mi,Yook, Kyoung-Soo,Lee, Woo-Hyung,Hong, Yongtaek,Lee, Jun-Yeob,Kang, In-Nam
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p. 5111 - 5117
(2013/11/06)
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- Carbazole-based conjugated polymer with tethered acetylene groups: Synthesis and characterization
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A novel carbazole-based conjugated polymer with tethered acetylenes, poly [(9,9-dioctyl)-2,7-fluorene-(N-octyl-3,6-carbazole)]-co-[(9,9-dioctyl)-2, 7-fluorene-(N-4-phenylacetylene)-3,6-carbazole)] (P-2), was successfully synthesized through the desilylati
- Lei, Yanli,Mi, Hongyu,Nurulla, Ismayil,Shi, Wei,Niu, Qiaoli,Wang, Yongli
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p. 138 - 147,10
(2020/08/20)
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- The synthesis and photovoltaic properties of A-D-A-type small molecules containing diketopyrrolopyrrole terminal units
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A series of novel A-D-A structured small molecule photovoltaic (PV) materials [CZ(TDPP)2, DPA(TDPP)2, PTZ(TDPP)2 and FL(TDPP)2] with diketopyrrolopyrrole (DPP) as an electron-withdrawing group were synthesized and characterized. These small molecular donors exhibit excellent solubility in common organic solvents. The density functional theory (DFT) calculations demonstrated the intramolecular charge transfer (ICT) behavior of the synthesized PV materials and an efficient charge separation was observed by a fluorescence quenching experiment. In addition, their photophysical and electrochemical properties show that they harvest sunlight over the entire visible spectrum range and keep appropriate energy levels to satisfy the requirement of solution-processable OSCs. Therefore, we explored the PV properties of the synthesized donors by fabricating BHJ solar cells with a typical structure of ITO/PEDOT:PSS/Donors: PC61BM/LiF/Al. Among them, CZ(TDPP)2 revealed a promising performance in PV devices with a power conversion efficiency (PCE) of 1.50%, along with an open-circuit voltage (VOC) of 0.66 V, a short-circuit current density (JSC) of 4.12 mA cm-2, and a fill factor (FF) of 0.44, under an illumination of AM 1.5G (80 mW cm-2).
- Zhang, Ling,Zeng, Shaohang,Yin, Lunxiang,Ji, Changyan,Li, Kechang,Li, Yanqin,Wang, Yue
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supporting information
p. 632 - 639
(2013/03/28)
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- Fluorescent pyrene-centered starburst oligocarbazoles with excellent thermal and electrochemical stabilities
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A series of pyrene-centered starburst oligocarbazoles (1-3) have been synthesized and well characterized. Based on photophysical, thermal and electrochemical studies in solutions and as thin films, all starburst molecules reveal a sky blue emission with a high efficiency (ΦF = 0.99 - 0.81) and excellent thermal and electrochemical stabilities. As OLED materials, these superior properties are helpful to enhance device stability and lifetime.
- Ren, Ming-Guang,Guo, Hui-Jun,Qi, Fei,Song, Qin-Hua
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p. 6913 - 6916
(2011/11/04)
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- The tuning of the energy levels of dibenzosilole copolymers and applications in organic electronics
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An understanding of the structure-function relationships of conjugated polymers is an invaluable resource for the successful design of new materials for use in organic electronics. To this end, we report the synthesis, characterisation and optoelectronic properties of a range of new alternating copolymers of dibenzosilole. Suzuki polycondensation reactions were used to afford a series of eight conjugated materials by the respective combination of either a 3,6- or 2,7-linked 9,9-dioctyldibenzosilole with 3,6-linked-N- octylcarbazole, triarylamine, oxadiazole and triazole monomers. The copolymers were fully characterised using 1H, 13C{1H} NMR spectroscopy, size exclusion chromatography (SEC), differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). The photophysical properties were determined using UV-Vis spectroscopy, photoluminescence (PL) measurements, cyclic voltammetry (CV) and photoelectron emission spectroscopy in air (PESA). The spectroscopic and electrochemical measurements were used to determine the materials' HOMO and LUMO energies and the values were correlated with the copolymer composition and structure. A selection of the copolymers (P4, P5 and P8) were evaluated as the active layer within single-layer polymer light emitting diodes (PLEDs), with the configuration: glass/ITO/PEDOT:PSS/emissive layer/Ba/Al, which gave low intensity electroluminescence. The selected copolymers were also evaluated as the organic semiconductor in bottom-gate, bottom-contact organic field effect transistors (OFETs). The best performing devices gave a maximum mobility of 3 × 10-4 cm2 V-1 s-1 and on/off current ratios of 105. The Royal Society of Chemistry 2011.
- Keyworth, Colin W.,Chan, Khai Leok,Labram, John G.,Anthopoulos, Thomas D.,Watkins, Scott E.,McKiernan, Mary,White, Andrew J. P.,Holmes, Andrew B.,Williams, Charlotte K.
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supporting information; experimental part
p. 11800 - 11814
(2011/11/07)
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- Molecular recognition of the antiretroviral drug abacavir: Towards the development of a novel carbazole-based fluorosensor
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Due to their optical and electro-conductive attributes, carbazole derivatives are interesting materials for a large range of biosensor applications. In this study, we present the synthesis routes and fluorescence evaluation of newly designed carbazole fluorosensors that, by modification with uracil, have a special affinity for antiretroviral drugs via either Watson-Crick or Hoogsteen base pairing. To an N-octylcarbazole-uracil compound, four different groups were attached, namely thiophene, furane, ethylenedioxythiophene, and another uracil; yielding four different derivatives. Photophysical properties of these newly obtained derivatives are described, as are their interactions with the reverse transcriptase inhibitors such as abacavir, zidovudine, lamivudine and didanosine. The influence of each analyte on biosensor fluorescence was assessed on the basis of the Stern-Volmer equation and represented by Stern-Volmer constants. Consequently we have demonstrated that these structures based on carbazole, with a uracil group, may be successfully incorporated into alternative carbazole derivatives to form biosensors for the molecular recognition of antiretroviral drugs. The Author(s) 2011. This article is published with open access at Springerlink.com.
- Idzik, Krzysztof Ryszard,Cywinski, Piotr J.,Cranfield, Charles G.,Mohr, Gerhard J.,Beckert, Rainer
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experimental part
p. 1195 - 1204
(2012/04/10)
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- ELECTRON DONATING ORGANIC MATERIAL, MATERIAL FOR PHOTOVOLTAIC ELEMENT, AND PHOTOVOLTAIC ELEMENT
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The invention aims at providing a photovoltaic device with high photoelectric conversion efficiency. The aim is attained by an electron donating organic material containing a benzothiadiazole compound in which (a) a benzothiadiazole skeleton and an oligothiophene skeleton are contained, (b) a band gap (Eg) is 1.8 eV or less, and (c) the level of the highest occupied molecular orbital (HOMO) is -4.8 eV or less, wherein said benzothiadiazole compound is formed by covalently combining the benzothiadiazole skeleton and the oligothiophene skeleton alternately, the proportion between the benzothiadiazole skeleton and the oligothiophene skeleton is within a range of 1:1 to 1:2 (however, excluding 1:1), and the number of thiophene rings contained in an oligothiophene skeleton is 3 or more and 12 or less.
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Page/Page column 32-33
(2011/01/12)
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- Carbazole Compounds as Host Materials for Triplet Emitters in Organic Light-Emitting Diodes: Tuning the HOMO Level without Influencing the Triplet Energy in Small Molecules
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A series of novel carbazole compounds was synthesized and tested for their suitability as host for triplet emitters in an organic-light emitting diode (OLED). In these compounds, a carbazole unit is either connected to other carbazole units to form carbazole dimers and trimers or to fluorene and oxadiazole derivatives to form mixed compounds. The HOMO level of carbazole compounds can be tuned by substitution at the 3, 6, and/or 9 positions. Making oligomers by connecting carbazole molecules via their 3 (3′) positions shifts the HOMO level to higher energy, while replacing alkyl groups at the 9 (9′) positions by aryl groups shifts the HOMO level to lower energy. Furthermore, it has been found that the triplet energy of these compounds is determined by the presence of poly(p-phenyl) chains in the molecular structure. By identifying the longest poly(p-phenyl) chain, one can predict whether a compound will be a suitable host for a high-energy triplet emitter. An overview of HOMO levels, singlet and triplet levels, and exchange energies is given for all carbazole compounds synthesized. Finally, OLEDs employing two selected carbazole compounds as host and fac-tris(2-phenylpyridine)-iridium (Ir(ppy) 3) as guest were constructed and characterized electrically.
- Brunner, Klemens,Van Dijken, Addy,Boerner, Herbert,Bastiaansen, Jolanda J. A. M.,Kiggen, Nicole M. M.,Langeveld, Bea M. W.
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p. 6035 - 6042
(2007/10/03)
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