33255-13-9

Usage

Chemical Properties

White crystalline powder

InChI:InChI=1/C14H11Br2N/c1-2-17-13-5-3-9(15)7-11(13)12-8-10(16)4-6-14(12)17/h3-8H,2H2,1H3

Upstream product

• 64-67-5 diethyl sulfate 
• 86-28-2 N-ethylcarbazole 
• 6825-20-3 3,6-dibromo-9H-carbazole 
• 57102-97-3 3-bromo-9-ethyl-9H-carbazole 
• 86-74-8 9H-carbazole 
• 75-03-6 ethyl iodide 
• 74-96-4 ethyl bromide 
• 106-94-5 propyl bromide 

Downstream Products

• 18782-45-1 3,6,9-triethyl-carbazole 
• 51545-42-7 9-ethyl-3,6-dimethyl-9H-carbazole 
• 1592-64-9 9-Ethyl-3,6-divinyl-9H-carbazole 
• 106176-05-0 9-Ethyl-9H-carbazole-3,6-dicarboxylic acid dibutyl ester 
• 1483-97-2 1,1′-(9-ethyl-9H-carbazole-3,6-diyl)diethanone 
• 797057-70-6 3,6-di-(9-carbazolyl)-9-ethylcarbazole 
• 1026991-04-7 3,6-di(2-naphthyl)-9-ethylcarbazole 
• 1026991-02-5 3,6-di(1-naphthyl)-9-ethylcarbazole 
• 1207729-81-4 N-ethyl-carbazole-3,6-diboronic acid 
• 1245648-53-6 3-bromo-6-(4-(diphenylamino)phenyl)-9-ethylcarbazole 
• 1245644-28-3 5-(3-(4-(diphenylamino)phenyl)-9-ethylcarbazole-6-yl)-3-hexylthiophene-2-carbaldehyde 
• 1245652-43-0 3-(5-(3-(4-(diphenylamino)phenyl)-9-ethylcarbazole-6-yl)-3-hexylthiophene-2-yl)-2-cyanoacrylic acid 
• 1519104-43-8 C₁₈H₁₄BrNS 
• 1039452-36-2 C₄₀H₃₀N₂S₃ 

Relevant academic research and scientific papers

New multi-phenylated carbazole derivatives for OLED through Diels-Alder reaction

We synthesized multi-phenylated carbazole derivatives such as 3,6-Bis[(2,3,4,5-tetraphenyl)phenyl]-9-ethylcarbazole(BTPEC) and 3,6-Bis(7,10-diphenyl-fluoranthene)-9-ethlycarbazole(BDPEC), through Diels-Alder reaction. These products were identified by NMR, Fab-Mass analysis. Electro-optical properties of these materials were characterized by cyclic voltammetry (CV) and, UV-visible and photoluminescence (PL) spectra. The maximum absorbance of BTPEC appeared at 307 nm and BDPEC showed maximum absorbance of 307 nm and 388 nm. And two compounds also exhibited PL peaks at 389 nm and 483 nm. When we used these two materials as hole injection layer(HIL) and hole transport layer(HTL) in OLED device, the devices showed about 3 cd/A and 2 cd/A, respectively.

Pyridination of hole transporting material in perovskite solar cells questions the long-term stability

In this work, for the first time, reactive radical-cation species present in hole-transporting materials were shown to react with tert-butylpyridine additive, routinely used in hole transporting layer composition. As a result, new pyridinated products were isolated and characterized by NMR and MS analysis. Additionally, their optical and photophysical properties (i.e., solid-state ionization potentials (Ip), cyclic voltammetry (CV), UV/vis characteristics, and conductivities) were determined. Formation of the pyridinated products was confirmed in the aged perovskite solar cells by means of mass spectrometry, and shown to have negative influence on the overall device performance. We believe that these findings will help improve the stability of perovskite devices by either molecular engineering of hole-transporting materials or utilization of less-reactive or sterically hindered pyridine derivatives.

Functionalised carbazole as a cathode for high voltage non-aqueous organic redox flow batteries

Prospective high reduction potential cathode materials have been proposed that can be used in non-aqueous redox flow battery applications. A new class of material, 3,6-dibromo-9-(p-tolyl)-9H-carbazole(3)incorporating a carbazole core, showing a very good reversibility is employed as the cathode material and dissolved oxygen in the solvent mixture is used as the anolyte material. Labile positions of the carbazole have been substituted with electron withdrawing groups, which increases the reduction potential of the redox couple. Apart from substituting the labile positions, we have also explored the possible structural modification responsible for stabilizing the cation radical of the carbazole moiety and obtained the reversible behavior thereafter. From this, it is evident that a free radical is stabilized upon delocalization of the charge in the molecule. The mass-transport and redox parameters, diffusion coefficient and heterogeneous electron transfer rate coefficient values are high enough to realize good battery performance. A solvent mixture of acetonitrile and dichloromethane (4?:?1) has been used in this work in order to increase the solubility of electroactive materials in the medium.

A side-chain engineering strategy for constructing fluorescent dyes with direct and ultrafast self-delivery to living cells

Organic fluorescent dyes with excellent self-delivery to living cells are always difficult to find due to the limitation of the plasma membrane having rigorous selectivity. Herein, in order to improve the permeability of dyes, we utilize a side-chain engineering strategy (SCES): adjusting the side-chain length of dyes to fine-tune the adsorption and desorption processes on the membrane-aqueous phase interfaces of the outer and inner leaflets of the plasma membrane. For this, a family of fluorescent derivatives (SPs) was prepared by functionalizing a styryl-pyridinium fluorophore with alkyl side-chains containing a different carbon number from 1 to 22. Systematic experimental investigations and simulated calculations demonstrate that the self-delivery rate of SPs with a suitable length side-chain is about 22-fold higher in SiHa cells and 76-fold higher in mesenchymal stem cells than that of unmodified SP-1, enabling cell-imaging at an ultralow loading concentration of 1 nM and deep penetration in turbid tissue and in vivo. Moreover, the SCES can even endow a membrane-impermeable fluorescent scaffold with good permeability. Further, quantitative research on the relationship between Clog?P and cell permeability shows that when Clog?P is in the range of 1.3-2.5, dyes possess optimal permeability. Therefore, this work not only systematically reports the effect of side-chain length on dye delivery for the first time, but also provides some ideal fluorescent probes. At the same time, it gives a suitable Clog?P range for efficient cellular delivery, which can serve as a guide for designing cell-permeant dyes. In a word, all the results reveal that the SCES is an effective strategy to dramatically improve dye permeability.

Pigment additives, method of manufacturing the same and pigment dispersion compositions containing the same

The present invention refers to novel pigment additive, manufacturing method thereof and relates to a pigment dispersion composition including, using additives pigment of the present invention optical properties surface, dispersibility and excelling in dispersion stability and have a color property, a pigment dispersion composition provides. (by machine translation)

NEW COMPOUNDS AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME

PURPOSE: A novel compound and an organic light emitting element containing the compound are provided to enhance lifetime, efficiency, electrochemical stability, and thermal stability of the element. CONSTITUTION: A compound used in an organic light emitting device is denoted by chemical formula 1. An organic light emitting element comprises: a first electrode; a second electrode facing the first electrode; and one or more organic layers between the first and second electrodes. The organic layers contain the compound of chemical formula 1. The organic layer comprises a light emitting layer. The organic layer further comprises a hole transport layer, a hole blocking layer, an electron blocking layer, an electron transport layer, or an electron injection layer. A method for manufacturing the organic light emitting element comprises: a step of preparing the first electrode on a substrate; a step of forming the organic layer containing the compound; and a step of forming the second electrode on the organic layer.

Synthesis and photophysical properties of doubly β-to-β bridged cyclic ZnII porphyrin arrays

A series of doubly β-to-β bridged cyclic ZnII porphyrin arrays were prepared by a stepwise Suzuki-Miyaura coupling reaction of borylated ZnII porphyrin with different bridge groups. The coupling of the building block of β,β′-diboryl ZnII porphyrin with different bridges provided the doubly β-to-β carbazole-bridged ZnII porphyrin array, the fluorene-bridged ZnII porphyrin array, the fluorenone-bridged ZnII porphyrin array, and the three-carbazole-bridged ZnII porphyrin ring. The structural assignment of was confirmed by the X-ray diffraction analysis, which revealed a highly symmetrical and remarkably bent syn-form structure. The incorporation of bridge units with different electronic effects results in different photophysical properties of the cyclic ZnII porphyrin arrays. Comprehensive photophysical studies demonstrate that the electron-withdrawing bridge fluorenone has the largest electronic interaction with the Zn II porphyrin unit among the series, thus resulting in the highest two-photon absorption cross-section values (σ(2)) of 6570±60 GM for. The present work provides a new strategy for developing porphyrin-based optical materials. Do you cross the bridge or do you fade away: Doubly β-to-β bridged cyclic ZnII porphyrin arrays with carbazole, fluorene, and fluorenone as bridges were constructed. The incorporation of bridge units with different electronic effects results in different photophysical properties of the cyclic ZnII porphyrin arrays.

Polymer and organic light emitting device including polymer

A polymer and an organic light-emitting device including the polymer are provided, wherein the polymer comprises a polymeric unit represented by the Formula: In which variables are as defined herein.

Efficient triphenylamine-based dyes featuring dual-role carbazole, fluorene and spirobifluorene moieties

Three triphenylamine-based organic dyes SD6, SD7, and SD8 containing the bulky dual-role moieties (fluorene, carbazole, and spirobifluorene) in the molecular frameworks were synthesized, characterized and applied in dye-sensitized solar cells (DSSCs). The effects of dual-role moieties of organic dyes on their photophysical, electrochemical, and photovoltaic properties have been investigated in detail. These dyes exhibit strong charge transfer absorption bands in the visible region. Their redox potential levels were estimated by cyclic voltammetry and found to suit well to the charge flow in DSSCs. Inserting the dual-role moieties as the secondary donor between the triphenylamine and thiophene units increased the electron density of the donor groups, therefore reduced the HOMO-LUMO band gaps. The combination of ultraviolet-visible (UV-vis) region broad absorption bands with fairly high extinction coefficients and appropriate redox properties observed in these triphenylamine-based dyes make them promising dyes for DSSCs. For a typical solar cell device based on dye SD6, the maximal monochromatic incident photon-to-current conversion efficiency (IPCE) can reach to ～73%, with a short-circuit photocurrent density (Jsc) of 14.25 mA/cm2, an open-circuit photovoltage (Voc) of 0.70 V, and a fill factor (FF) of 0.705, which corresponds to a power conversion efficiency (PCE) of 7.03%.

Highly efficient deep-blue emitting organic light emitting diode based on the multifunctional fluorescent molecule comprising covalently bonded carbazole and anthracene moieties

High performance deep-blue organic light-emitting diodes (OLEDs) have been investigated using new multifunctional blue emitting materials 3-(anthracen-9-yl)-9-ethyl-9H-carbazole (AC), 3,6-di(anthracen-9-yl)-9-ethyl-9H- carbazole (DAC), 3-(anthracen-9-yl-)-9-phenyl-9H-carbazole (P-AC), and 3,6-di(anthracen-9-yl)-9-phenyl-9H-carbazole (P-DAC) which comprise covalently bonded carbazole and anthracene moieties. We also have investigated the thermal, electrochemical, and morphological stability to find suitable molecular structure, consisting of carbazole and anthracene moieties. The non-doping deep-blue OLEDs using P-DAC, which showed the highest thermal, electrochemical, and morphological stability, proved the highest luminance efficiency and external quantum efficiency of 3.14 cd A-1 and 2.75%, with the Commission Internationale de l'Eclairage (CIE) chromaticity coordinates (0.162, 0.136) at 100 mA cm-2. Moreover, the doping devices using P-DAC as the host material showed blue emission, and the high luminance efficiencies and external quantum efficiencies of as high as 7.70 cd A-1 and 4.86% with CIE chromaticity coordinates (0.156, 0.136) and (0.156, 0.217) at 100 mA cm-2. Both the non-doping and doping devices using P-DAC uniquely exhibited high operational stability with virtually negligible efficiency roll-off over the broad current density range.