- Method for synthesizing 1-bromocarbazole by taking carbazole as raw material
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The invention discloses a method for synthesizing 1-bromocarbazole by taking carbazole as a raw material. The method comprises the following steps: mixing carbazole as a raw material with an acylation reagent, a catalyst and a reaction solvent, and carrying out acylation reaction to obtain an N-H substituted carbazole intermediate; forming a reaction system by using the carbazole intermediate obtained in the step (1) and a reaction solvent, dropwise adding a lithiation reagent to perform a lithium substitution reaction, and dropwise adding a bromination reagent to perform a bromination reaction after the reaction is completed to obtain a carbazole N-substituted 1-position bromination product; and (3) carrying out hydrolysis deprotection reaction on the carbazole N-substituted 1-position brominated product obtained in the step (2) to obtain a 1-bromocarbazole product. According to the method, phosphorus-containing compounds with serious pollution do not need to be used, the adopted raw material carbazole is easy to obtain and low in cost, post-treatment operation is simple and easy, the post-treatment cost is low, the problems that existing 1-bromocarbazole is high in production cost, complex in synthesis technological process, more in three wastes and heavy in pollution can be solved, the purity of the obtained 1-bromocarbazole is 99.5% or above, the obtained 1-bromocarbazole is high in purity, and the yield can reach more than 80%.
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Paragraph 0055; 0058-0061; 0062; 0065; 0066; 0069; 0070; ...
(2021/11/03)
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- Halogenated method of aromatic compound
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The invention belongs to the field of organic synthesis, and particularly relates to synthesis of aromatic halogens, in particular to arylamine. The invention discloses a synthesis method of a corresponding ortho-halogenated product from aromatic compounds such as carbazole and phenol. The method comprises the following steps: adding a metal sulfonate salt catalyst, aromatic amine, carbazole, phenol and other hydrogen - heteroatom-containing aromatic compound reaction substrates, a halogenation reagent and a reaction solvent at a specific reaction temperature. After the drying agent is dried, the yield of the reaction product and the nuclear magnetic characterization determining structure are determined by column chromatography. The reaction product yield is determined by gas chromatography. By adopting the method, under the cheap metal salt catalyst, a plurality of ortho-substituted brominated and chloro products can be obtained with moderate to excellent yield.
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Paragraph 0091-0094; 0186-0188; 0195-0197
(2021/11/10)
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- ORGANOMETALLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME
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An organometallic compound represented by Formula 1: wherein, in Formula 1, groups and variables are the same as described in the specification.
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Paragraph 0257-0259
(2017/02/24)
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- 1-bromo carbazole preparation method
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The invention discloses a 1-bromo carbazole preparation method, and belongs to the field of organic chemical synthesis. The preparation method specifically comprises: carrying out an Ullmann coupling reaction on raw materials such as o-bromoaniline and o-
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Paragraph 0057; 0058; 0063; 0064; 0068; 0069; 0073; 0074
(2017/11/29)
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- Visible-Light-Induced Synthesis of Carbazoles by in Situ Formation of Photosensitizing Intermediate
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A visible-light-induced synthesis of N-H carbazoles from easily accessible 2,2′-diaminobiaryls in the absence of any external photosensitizer is reported. The process only requires tBuONO and natural resources, visible light, and molecular oxygen for the synthesis of N-H carbazoles. Experimental and computational studies support that the in situ formation of a visible-light-absorbing photosensitizing intermediate, benzocinnoline N-imide, is responsible for the activation of triplet molecular oxygen to singlet oxygen that, in turn, promotes the synthesis of carbazole.
- Chatterjee, Tanmay,Roh, Geum-Bee,Shoaib, Mahbubul Alam,Suhl, Chang-Heon,Kim, Jun Soo,Cho, Cheon-Gyu,Cho, Eun Jin
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p. 1906 - 1909
(2017/04/11)
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- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
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Disclosed is a compound represented by chemical formula 1. Also, disclosed is an organic electronic element comprising a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, wherein the organic layer includes the compound represented by chemical formula 1. If the compound represented by chemical formula 1 is included in the organic layer, light emitting efficiency, stability, engineering life, etc. can be improved.(110) Substrate(120) Positive electrode(130) Hole-injection layer(140) Hole transport layer(141) Buffer layer(150) Light emitting layer(151) Light-emitting assisting layer(160) Electron transport layer(170) Electron injection layer(180) Negative electrodeCOPYRIGHT KIPO 2016
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Paragraph 0217; 0220; 0221
(2016/10/07)
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- NEW DIBENZOFURANS AND DIBENZOTHIOPHENES
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The present invention relates to compounds of formula (I) which are characterized in that they are substituted by at least one nitrile substituted carbazolyl group and their use in electronic devices, especially electroluminescent devices. When used as el
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- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
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The present invention provides a novel compound to improve light emission efficiency and stability of an element and to extend lifespan of the element, an organic electronic element using the same, and an electronic device thereof. The compound is represented by chemical formula 1, wherein m is a constant in the range of zero and four, and n is a constant in the range of zero and three.(140) Hole transfer layer(141) Buffer layer(150) Light emitting layer(151) Light-emitting assisting layer(160) Electron transfer layer(170) Electron injection layer(180) Negative electrode(130) Hole injection layer(120) Positive electrode(110) SubstrateCOPYRIGHT KIPO 2015
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Paragraph 0135-0139; 0147; 0148; 0222-0226; 0229; 0230
(2016/10/08)
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- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
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Provided in the present invention are a novel compound which can improve light emitting efficiency, stability, and life, an organic electronic element using the same, and an electronic device thereof. The organic electronic element is characterized by comprising a first electrode; a second electrode; and an organic substance layer located between the first electrode and the second electrode, wherein the compound is contained in the organic substance layer. The organic electronic element is characterized by having the compound contained in at least one layer among a hole injection layer, a hole transfer layer, an light emitting auxiliary layer, or a light emitting layer of an organic substance layer.(140) Hole transfer layer(141) Buffer layer(150) Light emitting layer(151) Auxiliary light emitting layer(160) Electron transfer layer(170) Electron injection layer(180) Negative electrode(130) Hole injection layer(120) Positive electrode(110) SubstrateCOPYRIGHT KIPO 2015
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- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
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The present invention provides a novel compound which can improve light emitting efficiency, stability, and durability of an element, an organic electronic element, and an electronic device thereof. The organic electronic element comprises: a first electrode; a second electrode; and an organic layer located between the first electrode and the second electrode, wherein the compound is included in the organic layer.(110) Substrate(120) Positive electrode(130) Hole injection layer(140) Hole transfer layer(141) Buffer layer(150) Light emitting layer(151) Light-emitting assisting layer(160) Electron transfer layer(170) Electron injection layer(180) Negative electrodeCOPYRIGHT KIPO 2015
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Paragraph 0140-0141; 0144-0145
(2016/10/09)
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- FLUORSCENT DYES WITH LARGE STOKES SHIFTS
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Herein are disclosed fluorescent dyes based around a framework for a ligand comprising a pyridyl group linked to a diaryl anilido unit. A variety of ligands based on this framework are disclosed. The ligands chelate to a BF2 center to produce the fluorescent dye. The disclosed dyes combine longer Stokes shifts (approximately 100 nm) with increased quantum yields. They are also photostable in aqueous and organic solutions for several hours. These dyes may be used in the labeling of biomolecules for bioimaging and assays. Also disclosed are methods for the synthesis of these dyes.
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Paragraph 0081-0084
(2014/08/06)
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- Transition-metal-free direct arylation: Synthesis of halogenated 2-amino-2′-hydroxy-1,1′-biaryls and mechanism by DFT calculations
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A transition-metal-free, regioselective direct aryl-aryl bond-forming process for the synthesis of halogenated 2-amino-2′-hydroxy-1,1′- biaryls that are currently either inaccessible or challenging to prepare using conventional methods is disclosed. The addition of ArMgX to an o-halonitrobenzene at low temperature generates a transient N,O- biarylhydroxylamine that rapidly undergoes either [3,3]- or [5,5]-sigmatropic rearrangement in one-pot to form a 2-amino-2′-hydroxy-1,1′-biaryl or 1-amino-1′-hydroxy-4,4′-biaryl, respectively. The periselectivity is controlled by the choice of solvent and temperature. This direct arylation process is also readily scalable (1-10 mmol). DFT calculations suggest that from the N,O-biarylhydroxylamine intermediate there is a low-energy stepwise pathway that involves initial Mg-mediated N-O bond cleavage followed by pathway branching toward either [3,3]- or [5,5]-rearrangement products via C-C bond formation and rearomatization.
- Gao, Hongyin,Ess, Daniel H.,Yousufuddin, Muhammed,Kuerti, Laszlo
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p. 7086 - 7089
(2013/06/26)
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- A versatile route to benzocanthinones
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Benzocanthinone (1) and five analogs (10, 12-15) were prepared by radical-induced cyclizations of halo N-aroyl derivatives of β-carboline and carbazole.
- Markgraf, J. Hodge,Dowst, Adrian A.,Hensley, Laurel A.,Jakobsche, Charles E.,Kaltner, Cindy J.,Webb, Peter J.,Zimmerman, Patrick W.
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p. 9102 - 9110
(2007/10/03)
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- Preparation of polyfunctional arylmagnesium reagents bearing a triazene moiety. A new carbazole synthesis
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(Chemical Equation Presented) The reaction of iodo- or bromo-substituted aryltriazenes with i-PrMgCl·LiCl generates the corresponding magnesiated derivatives which react with various electrophiles (acid chlorides, 3-iodoenones, allylic halides, aldehydes)
- Liu, Ching-Yuan,Knochel, Paul
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p. 2543 - 2546
(2007/10/03)
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- Synthesis of carbazoles from N-(N,N-diarylamino)phthalimides with aluminum chloride via diarylnitrenium ions
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Generation of diarylnitrenium ions from N-(N,N-diarylamino)phthalimides by treatment with AlCl3 in benzene or in 1,2-dichloroethane leads to formation of carbazoles by intramolecular C-C bond formation. The reaction proceeds in synthetically useful yields.
- Kikugawa,Aoki,Sakamoto
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p. 8612 - 8615
(2007/10/03)
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- Outer-sphere electron transfer from carbazoles to halomethanes. Reduction potentials of halomethanes measured by fluorescence quenching experiments.
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Kinetic studies on the photoinduced electron transfer reduction of a variety of halomethanes in acetonitrile and ethanol at 298 K are reported in terms of the quenching rate constants (kq) with a series of reductants (carbazoles and anthracenes) whose one-electron oxidation potentials (Eox) have been measured again in the present work vs. SCE and independently vs. ferrocene. The Rehm-Weller Gibbs energy relationship is applied to determine the fundamental parameters for the one-electron reduction, i.e., the one-electron reduction potentials (ERX/RX) of the halomethanes and the intrinsic barrier for the electron transfer reduction (ΔG?o). The ERX/RX- values obtained were related to the concerted electron transfer-bond breaking reduction potentials (ERX/R·+x-) and the standard free enthalpies of dissociation of RX- (ΔGo,dissRX-) were estimated in each solvent. Additionally, the one-electron reduction potential (ERX/RX-) values estimated in acetonitrile were also related to different thermodynamic parameters such as electron affinity (EA), LUMO-HOMO energy differences (ΔE) and the bond dissociation energy (DRX). Optimized geometry, EA and ΔE for halomethanes were calculated by an ab initio method at the B3LYP level using 3-21G, 6-31 + G(d,p) and G-311 + G(3df,2pd) basis sets. In all these cases good linear correlations were obtained. The ΔG?o values obtained are compared with those calculated using the equation ΔG?o = λ/4 with λ = λi + λo where the solvent reorganization energy (λo) and the inner-sphere reorganization energies (λi) associated with the structural change upon the electron-transfer process were calculated, the former by using the Marcus-Hush model and the latter by using semiempirical and ab initio molecular modeling and QSAR properties. Results obtained from the preparative irradiation of carbazoles in the presence of halomethanes, which are consistent with a photoinduced electron transfer mechanism are also discussed.
- Bonesi, Sergio M.,Erra-Balsells, Rosa
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p. 1583 - 1595
(2007/10/03)
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