cas 194-59-2, 7H-Dibenzo[c,g]carbazole | Articles data

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Dibenzo[: C, g] indolo[3,2,1- jk] carbazole as a new chromophore for blue organic light-emitting diodes
A novel sky-blue fluorescent emitter was developed from a novel dibenzo[c,g]indolo[3,2,1-jk]carbazole chromophore. A photoluminescence quantum yield of 94.1%, maximum quantum efficiency of 6.2%, high luminance over 80000 cd m-2, and 4.8 times extension of the operational lifetime compared to that of a pyrene derived blue emitter were realized from the fabricated device.
Patil, Vilas Venunath,Lee, Kyung Hyung,Lee, Jun Yeob
p. 14301 - 14305
(2019)
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Acid-catalyzed condensation of 2,2′-diamino-1,1′-biaryls for the synthesis of benzo[c]carbazoles
2,2′-Diamino-1,1′-biaryls were found to undergo ring-closure condensation reaction to afford benzo[c]carbazoles in good to excellent yield. Coupled with the synthesis of 2,2′-biaryldiamines from diaryl hydrazides via [3,3]-sigmatropic rearrangement, it constitutes a new efficient synthetic method for benzo[c]carbazoles and related compounds.
Lim, Byong-Yun,Choi, Min-Kyung,Cho, Cheon-Gyu
p. 6015 - 6017
(2011)
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An electroluminescent compound and an electroluminescent device comprising the same
The present invention relates to a novel organic light emitting compound represented by chemical formula I, which is used as a material of an organic material layer such as a light emitting layer, a hole transport layer, an electron transport layer, an electron blocking layer, and a light efficiency improvement layer in an organic light emitting device, and thus can realize luminous properties such as remarkably excellent luminous efficiency and quantum efficiency. The present invention also relates to the organic light emitting device comprising the novel organic light emitting compound.
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(2021/02/05)

COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
The present invention provides: a novel mixture capable of improving luminous efficiency, stability, and lifespan of an element; an organic electronic element which uses the same; and an electronic device thereof. By using the mixture according to the present invention as a phosphorescent host material, it is possible to achieve high luminous efficiency and low driving voltage of the organic electronic element, and also significantly improve a lifespan of the element.(110) Substrate(120) Anode(130) Hole injection layer(140) Hole transport layer(141) Buffer layer(150) Light emitting auxiliary layer(151) Light emitting layer(160) Electron transport layer(170) Electron injection layer(180) CathodeCOPYRIGHT KIPO 2020
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Paragraph 0525; 0538-0540; 0547-0548; 0572-0574; 0579-0580

(2020/05/26)

COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND A ELECTRONIC DEVICE THEREOF
The present invention relates to a novel compound, an organic electric element using the same, and an electronic device thereof. According to the present invention, a luminous efficiency, a color purity and a lifespan of the element can be improved and a driving voltage can be lowered. The organic electric element comprises: an anode; a cathode; and an organic material layer formed between the anode and the cathode.
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Paragraph 0134; 0140-0143; 0155-0158

(2020/05/30)

COMPOUND AND ORGANIC LIGHT EMITTING ELEMENT COMPRISING SAME
Provided is a compound of Chemical Formula 1: and an organic light emitting device including the same.
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(2020/05/14)

METHOD OF SYNTHESIZING ORGANIC COMPOUND HAVING FUSED CARBAZOLE SKELETON
PROBLEM TO BE SOLVED: To provide a synthesis method that increases the yield of an organic compound having a fused carbazole skeleton. SOLUTION: In synthesis of an organic compound having a fused carbazole skeleton, the chlorine content in a compound having a fused carbazole skeleton used as an ingredient is made 10 ppm or less thereby allowing increase of the yield of the organic compound having the fused carbazole skeleton. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT
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Paragraph 0184; 0192-0214

(2019/09/21)

Synthesis of N-Alkyl and N-H-Carbazoles through SNAr-Based Aminations of Dibenzothiophene Dioxides
Alkyl amines have become available for the synthesis of diverse N-alkyl carbazoles through twofold SNAr aminations of dibenzothiophene dioxides by using alkali metal bases. Of particular importance is the choice of counter cations on alkali metal bases, that is, i) the use of Li base for the efficient intermolecular reaction and ii) the sequential addition of heavier alkali metal bases (Na, K, or Cs) to promote intramolecular cyclization in a one-pot manner. This protocol also enables the cascade synthesis of N-H-carbazoles by using 2-phenylethylamine by removal of the 2-phenethyl group from N-(2-phenethyl) carbazoles in a single operation.
Kaga, Atsushi,Nogi, Keisuke,Yorimitsu, Hideki
supporting information
p. 14780 - 14784
(2019/11/13)

CARBAZOLE DERIVATIVE AND BIPHENYL DERIVATIVE PRODUCTION METHOD AND NOVEL BIPHENYL DERIVATIVE
PROBLEM TO BE SOLVED: To provide a method for high-yield mass production of a carbazole derivative by a simple process using inexpensive materials. SOLUTION: A method for producing a carbazole derivative represented by general formula (3) comprises reacting an aminating agent with a 2,2'-dihydroxybiphenyl derivative represented by general formula (1). SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT
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Paragraph 0048-0053; 0061

(2019/05/21)

An intermolecular C-H oxidizing strategy to access highly fused carbazole skeletons from simple naphthylamines
Highly π-extended hetero-cyclic/aromatic skeletons are of great importance as they can be utilized in many organic material based technologies. Therefore, developing efficient, pre-activation-free, synthetic procedures for the rapid build-up of these complex structures remains a high priority objective. The herein presented approach delivers highly fused carbazole skeletons from simple naphthylamine derivatives.
Rank, Christian K.,Jones, Alexander W.,Wall, Tatjana,Di Martino-Fumo, Patrick,Schr?ck, Sarah,Gerhards, Markus,Patureau, Frederic W.
supporting information
p. 13749 - 13752
(2019/11/19)

Derivative containing azaanthracene structure, preparation method of derivative and organic light-emitting device comprising derivative
The invention provides a derivative containing azaanthracene structure, a preparation method of the derivative and an organic light-emitting device comprising the derivative and belongs to the technical field of organic photoelectric materials. The derivative has a structure shown in formula (I). luminous performance of the derivative is improved by adjusting R3 and R4 on the azaanthracene structure and adjusting benzene ring group in benzocarbazole structure and by other means, so that the derivative prepared allows easy dispersion and migration of charge and has good stability, high glass transition temperature and good film-forming performance. The organic light-emitting device prepared using the derivative containing azaanthracene structure provided herein has high luminous efficiencyand low drive voltage, as a main material in the organic light-emitting device, the derivative can effectively improve luminous efficiency of an OLED device; the organic light-emitting device is better than existing common OLED devices.
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(2018/05/01)

Organic electroluminescent material and organic light emitting device
The invention provides an organic electroluminescent material and an organic light emitting device and belongs to the technical field of organic photoelectric materials. The structure of the organic electroluminescent material contains a structure similar to carbazole; and by linking more conjugated groups, a glass transition temperature of the organic electroluminescent material can be effectively raised, the possible crystallization in use is reduced, and the ability of transporting holes is stronger. Compared with the prior art, the organic electroluminescent material is applied to the organic light emitting device and has relatively high light emitting efficiency and longer service life when being particularly used as a light emitting material.
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(2018/03/25)

Dibenzcarbazole type compound and organic luminescent device thereof
The invention provides a dibenzcarbazole type compound and an organic luminescent device thereof, and relates to the technical field of organic photoelectric materials. A carbazole type structure hasa higher oxidation-reduction potential value and has good stability under an air or illumination condition, and a condensed ring type rigid and dense structure is introduced, so that the thermal stability of the obtained compound is improved. The dibenzcarbazole type compound is used for preparing the organic luminescent device; especially, when the dibenzcarbazole type compound serves as a main material of the organic luminescent device, a carbazole type main material with a rigid structure has higher glass transition temperature, thereby being favorable for prolonging the service life of theorganic luminescent device; and the dibenzcarbazole type compound has the advantages of being high in efficiency and not liable to crystallize and is superior to an existing common OLED (Organic Light Emitting Diode) device.
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(2018/06/15)

One-pot heterocyclic ring closure of 1,1′-bi-2-naphthol to 7H-dibenzo[c,g]carbazole
An operationally simple ring closure of racemic 1,1′-bi-2-naphthol (BINOL) yielded the heterocyclic aromatic compound 7H-dibenzo[c,g]carbazole (DBC). This one-pot method gave a good conversion and is suitable for gram-scale synthesis. DBC derivatives have high thermal durability, amorphous and crystalline structures with unique morphological properties, and semi-conducting behavior with potential applications in organic electronics.
Hassan, Fathy,Kawamoto, Masuki,Salikolimi, Krishnachary,Hashizume, Daisuke,Hirose, Takuji,Ito, Yoshihiro
supporting information
p. 99 - 102
(2017/12/28)

Visible-Light-Induced Synthesis of Carbazoles by in Situ Formation of Photosensitizing Intermediate
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
supporting information
p. 1906 - 1909
(2017/04/11)

COMPOUND FOR ORGANIC ELECTRIC ELEMENT, ORGANIC ELECTRIC ELEMENT COMPRISING THE SAME AND ELECTRONIC DEVICE THEREOF
In the present invention, provided is a compound represented by chemical formula 1. In addition, provided is an organic electric element which comprises a first electrode, a second electrode, and an organic matter layer. The organic matter layer is embedded between the first electrode and the second electrode, and includes a compound represented by chemical formula 1. If the organic matter layer of an organic electric element comprises the compound represented by chemical formula 1, driving voltage of the organic electric device can be reduced and luminous efficiency, color purity, and lifetime of the organic electric device can be enhanced.(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 0134; 0143; 0146; 0147

(2016/10/08)

Light-emitting element, light-emitting device, electronic device, and lighting device
Provided is a light-emitting element which has high emission efficiency and a long lifetime and is driven at low voltage. The light-emitting element includes an EL layer between a pair of electrodes. The EL layer includes a compound which gives a first peak at a m/z of around 266.10 in a mass spectrum.
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(2016/03/06)

AROMATIC COMPOUNDS AND ORGANIC ELECTRONIC DEVICE USING THE SAME
The present invention relates to an organic electronic device wherein an organic substance layer has a novel compound which improves the service life, efficiency, driving voltage reduction, and stability of the organic electronic device. More specifically, in the present invention, the organic electronic device is an electrode using holes and/or electrons and a device which needs the exchange of electric charges between organic substances. The organic electronic device is divided largely into two devices by an operation principle.
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Paragraph 0384; 0391; 0392

(2017/01/09)

Easily oxidizable triarylamine materials with naphthalene and binaphthalene core: structure–properties relationship
We devised and synthesized a series of electron-rich compounds featuring diphenylamine, carbazole or dibenzo[c,g]carbazole connected via phenylacetylene linkers to an aromatic central unit. The key synthetic step was a high yielding cross coupling reaction between halogenated (bi)naphthalene and organometallic reagents prepared in situ from terminal alkynes (side-arms). By masking one of the iodo functions with a diethyltriazenyl group in the side-arm precursors, we efficiently circumvented the formation of doubly aminated by-products. Although one step longer, this approach led to higher yields of terminal alkynes than the direct coupling route. Spectroscopic and electrochemical measurements supported by computational evidence revealed that conjugation in the 1,4-disubstituted naphthalene backbone is superior to the 1,5 or 2,6 substituted cores. The diphenylamine derivative gets oxidized more readily when compared to its carbazole analogs. Expanding the core to binaphthalene did not alter electronic properties, but influenced the physical characteristics significantly.
Kerner, Luká?,Gmucová, Katarína,Ko?í?ek, Jozef,Pet?í?ek, Václav,Putala, Martin
supporting information
p. 7081 - 7092
(2016/10/14)

COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
The present invention provides a novel compound capable of improving light-emitting efficiency, stability, and lifespan of an element, an organic electronic element using same and an electronic device thereof.(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 2016
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Paragraph 0152; 0153; 0154

(2016/10/07)

Oxidative skeletal rearrangement of 1,1′-binaphthalene-2,2′- diamines (BINAMs) via C-C bond cleavage and nitrogen migration: A versatile synthesis of U-shaped azaacenes
An oxidative skeletal rearrangement of 1,1′-binaphthalene-2,2′- diamines (BINAMs) that involves the cleavage of a strong C-C single bond of the binaphthalene unit and the nitrogen migration has been discovered. The unprecedented rearrangement enables access to a series of U-shaped azaacenes otherwise difficult to prepare in a selective manner by classical methods. Moreover, physicochemical properties of the unique azaacenes have been comprehensively investigated. This journal is the Partner Organisations 2014.
Takeda, Youhei,Okazaki, Masato,Minakata, Satoshi
supporting information
p. 10291 - 10294
(2014/08/18)

An efficient and practical synthesis of BINAM derivatives by diastereoselective [3,3]-rearrangement
This work describes an efficient, practical, and diastereoselective synthesis of enantiomerically pure BINAM derivatives by utilizing the acid-catalyzed [3,3]-sigmatropic rearrangement of readily accessible N-(-)-menthoxycarbonyl-diaryl hydrazines as a key step. The yield of the rearrangement is very high and two diastereomers thus obtained are easily separable.
Li, Bing,Zhang, Shengyong,Chen, Weiping
p. 1002 - 1007
(2014/08/18)

DIBENZO[c,g]CARBAZOLE COMPOUND, LIGHT-EMITTING ELEMENT, LIGHT-EMITTING DEVICE, DISPLAY DEVICE, LIGHTING DEVICE AND ELECTRONIC DEVICE
Provided is a novel compound which can be used for a transport layer or as a host material or a light-emitting material in a light-emitting element and with which a high-performance light-emitting element can be manufactured. A dibenzo[c,g]carbazole compound in which an aryl group having 14 to 30 carbon atoms and including at least anthracene is bonded to nitrogen of a dibenzo[c,g]carbazole derivative is synthesized. By use of the dibenzo[c,g]carbazole compound, a light-emitting element having very good characteristics can be obtained.
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Paragraph 0227; 0228

(2013/03/26)

Organocatalytic aryl-aryl bond formation: An atroposelective [3,3]-rearrangement approach to BINAM derivatives
Herein we disclose an organocatalytic aryl-aryl bond-forming process for the regio- and atroposelective synthesis of 2,2′-diamino-1,1′- binaphthalenes (BINAMs). In the presence of catalytic amounts of axially chiral phosphoric acids, achiral N,N′-binaphthyl hydrazines undergo a facile [3,3]-sigmatropic rearrangement to afford enantiomerically enriched BINAM derivatives in good to excellent yield. This transformation represents the first example of a metal-free, catalytic C(sp2)-C(sp2) bond formation between two aromatic rings with concomitant de novo atroposelective installation of an axis of chirality. Density functional calculations reveal that, in the transition state for C-C bond formation, the phosphoric acid proton of the catalyst is fully transferred to one of the N-atoms of the substrate, and the resulting phosphate acts as a chiral counterion.
Li, Gong-Qiang,Gao, Hongyin,Keene, Craig,Devonas, Michael,Ess, Daniel H.,Kürti, László
supporting information
p. 7414 - 7417
(2013/06/27)

Acid-catalyzed [3,3] sigmatropic rearrangement of N-Cbz-diaryl hydrazide for the synthesis of mono-N-Cbz-1,1′-biaryl-2,2′-diamine
N-Cbz-Diaryl hydrazides undergo acid-catalyzed [3,3] sigmatropic rearrangement to afford N-Cbz-1,1′-biaryl-2,2′-diamines. The resultant products can be versatile synthetic platforms for a wide variety of C2- and/or nonsymmetric axially chiral ligands and organocatalysts. N-Cbz-Diaryl hydrazides bearing either a neutral or electron-donating group underwent highly efficient acid-catalyzed [3,3] sigmatropic rearrangement to afford N-Cbz-1,1′-biaryl-2,2′-diamines. The resultant products allow elaboration of various new C2- and/or nonsymmetric axially chiral ligands or organocatalysts.
Suh, Sung-Eun,Park, In-Keol,Lim, Byeong-Yun,Cho, Cheon-Gyu
p. 455 - 457
(2011/03/22)

Synthesis of primary aryl amines through a copper-assisted aromatic substitution reaction with sodium azide
(Figure Presented) A method is presented by which aryl halides and azides are converted to the corresponding primary aryl amines with copper(I) and sodium azide.
Markiewicz, John T.,Wiest, Olaf,Helquist, Paul
supporting information; experimental part
p. 4887 - 4890
(2010/10/19)

Structure of dinaphtho[2,1-b:1,2'-d]-five-membered ring aromatic heterocycles
A comparison between the X-ray structures of a series of binaphthyl-substituted five-membered aromatic heterocycles la-e, comprising pyrrole, furan, phosphole, thiophene and others, enlightens the effect of the heteroatom on the distortion of the molecules and the differences with the fully aromatic helicene, If (dibenzophenanth'ene). The X-ray data were either taken from the literature (le, le and If) or from compounds prepared in the course of the present study (la and Id). The furan Ib has also been prepared by new methods but its crystals were not suitable for X-ray analysis. The X-ray structures of the tetrahydro-substituted nitrogen and oxygen heterocycles 2a and 2b are also reported. The energy barrier to racemization has been determ ned by line-shape analysis of VT-NMR spectra for those.molecules where the presence of a substituent at the heteroatom and a high pyramidal inversion barrier render the naphthyl protons at the 1 and 13 position non equivalent (i.e. in le, Id', and Id").
Fabbri, Davide,Dore, Antonio,Gladiali, Serafino,De Lucchi, Ottorino,Valle, Giovanni
p. 11 - 18
(2007/10/03)

Selective Cross-Coupling of 2-Naphthol and 2-Naphthylamine Derivatives. A Facile Synthesis of 2,2',3-Trisubstituted and 2,2',3,3'-Tetrasubstituted 1,1'-Binaphthyls
The novel 1,1'-binaphthyls with OH and/or NHR (R = H or Ph) groups in the 2,2'-positions and with additional methoxycarbonyl group(s) in the 3- or 3,3'-positions (13-18) have been synthesized from their respective precursors 1-5 by the CuCl2/t-BuNH2-mediated oxidative cross-coupling.In most cases, the chemoselectivity was good, and the cross-coupled products 11-18 were obtained in fair to excellent yields.Binaphthyls 6-10, resulting from the selfcoupling, and carbazoles 19-23 have been identified as byproducts.Ab initio calculations and electrochemical measurements have been employed to account for the observrd selectivity.
Smrcina, Martin,Vyskocil, Stepan,Maca, Bohumil,Polasek, Miroslav,Claxton, Thomas A.,et al.
p. 2156 - 2163
(2007/10/02)

The Synthesis of some Alkylbenzocarbazoles
The preparation is described of five known and eight novel carbazole derivatives, the latter including compounds with alkyl side-chains.
Katrizky, Alan R.,Wang, Zuoquan
p. 671 - 675
(2007/10/02)

Heavy-Atom Kinetic Isotope Effects in the Acid-Catalysed and Thermal Rearrangements of 2,2'-Hydrazonaphthalene. Transition-State Differences in their Concerted Rearrangements
Acid-catalyzed (70percent aqueous dioxane at 0 deg C) and thermal rearrangement (95percent ethanol at 80 deg C) of 2,2'-hydrazonaphthalene (1) into 2,2'-diamino-1,1'-binaphthyl (2) have been shown to be concerted, -sigmatropic shifts.This was accomplished by measuring the nitrogen and carbon kinetic isotope effects (KIE), for which purpose mixtures of 1 with 1 and 1 were used.KIE were calculated from whole-molecule mass ratios, measured by multiscan mass spectrometry, in the bis(trifluoroacetyl) derivative of product 2, isolated after low and high conversions.The results (averaged) were, for two isotopic atoms, k(14N)/k(15N') = 1.0904, k(12C)/k(13C) = 1.0086 in the one-proton, acid-catalyzed rearrangement and 1.0611 and 1.0182, respectively, in the neutral, thermal rearrangement.These results indicate that although the rearrangements are concerted processes, the breaking of the N-N bond and the forming of the C-C bond proceed to different extents in the transition states.Furthermore, the differences in the timing of these events is greater in the acid-catalyzed than in the thermal rearrangement, a difference which may be attributable to earlier C-C bonding in the polar transition state of the former.
Shine, Henry J.,Gruszecka, Ewa,Subotkowski, Witold,Brownawell, Marilyn,Filippo, Joseph San, Jr.
p. 3218 - 3223
(2007/10/02)