- Palladium-catalyzed synthesis of triarylamines from aryl halides and diarylamines
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Various triarylamines can be readily prepared in excellent yields by palladium-catalyzed cross-coupling reaction of aryl halides and diarylamines. The amination reaction takes place rapidly by using the catalyst combination of Pd(OAc)2 and a bulky and electron-rich ligands, P(t-Bu)3.
- Yamamoto, Toshihide,Nishiyama, Masakazu,Koie, Yasuyuki
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- Organic amorphous material N,N,N,N′-tetraaryl(Ar12Ar2 2)-1,1′-biphenyl-4,4′-diamine
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A series of N,N,N,N′-tetraaryl(Ar12Ar2 2)-1,1′-biphenyl-4,4′-diamine were synthesized by the Pd(0) catalyzed C-N bond formation methodology. The physical properties, including glass transition temperature (Tg), melting point (Mp) and oxidation potential were measured. For Ar1 = 2-naphthyl and Ar2 = 3-toly (4f) and Ar2 = 3-ethylphenyl(4h), the DSC charts indicate that they have Tg, but no observable Mp. These two compounds are amorphous in solid state. The X-ray powder diffraction pattern of 4f further confirmed that it is truly amorphous throughout the temperature range in which it is solid. Therefore, we have demonstrated that a low molecular weight organic solid can be amorphous. This is an important aspect in the preparation of morphologically stable amorphous thin film. Other compounds with Ar1 = Ph, 1-naphthyl while Ar2 = 3-toly or 3-ethylphenyl are normal compounds with both Tg and Mp when prepared in their glassy state by rapid cooling of their melt. The oxidation potentials for compounds with Ar1 = 1-naphthyl and 2-naphthyl and identical Ar2 are exactly the same. The molecular structural features must be important factors for an organic solid to be in the amorphous state.
- Maiti,Wang,Cheng,Huang,Chao
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- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND A ELECTRONIC DEVICE THEREOF
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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 0335-0337
(2020/05/30)
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- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING SAME, AND ELECTRONIC DEVICE COMPRISING SAME
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The present invention provides a novel compound capable of improving the luminous efficiency, stability and life of an element, an organic electronic element using the same, and an electronic device comprising same.
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Paragraph 0125; 0167-0168
(2019/08/20)
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- ORGANIC MIXTURE, COMPOSITION, AND ORGANIC ELECTRONIC COMPONENT
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Disclosed in the present application is an organic mixture. The organic mixture comprises two organic compounds H1 and H2. The organic compound H1 has electron transmission performance, and the organic compound H1 satisfies: Δ((LUMO+1)?LUMO)≥0.1 eV, and min((LUMO(H1)?HOMO(H2), LUMO(H2)?HOMO(H1))≤min(ET(H1), ET(H2)). The organic compound H1 and the organic compound H2 are easy to form exciplexes and have balanced electron transmission properties, the organic compound Hi has high stability of electron transmission, and accordingly the efficiency and the service life of related electronic components can be effectively improved, and a feasible solution for improving overall performance of the electronic components is provided.
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Paragraph 0208-0209
(2020/01/03)
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- Compound, organic electric element using the same, and an electronic device thereof
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A compound represented by Formula 1. An organic electric element includes a first electrode, a second electrode, and an organic material layer including the compound of Formula 1. The organic material layer include a light emitting layer, a hole transport layer including a compound represented by Formula 2, and an emission-auxiliary layer including the compound represented by Formula 1. When the organic electric element includes the compound in the organic material layer, luminous efficiency, color purity, and life span can be improved.
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Page/Page column 242; 243; 277; 280
(2018/08/07)
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- Metal-Free Oxidative C-C Coupling of Arylamines Using a Quinone-Based Organic Oxidant
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A variety of arylamines are shown to undergo oxidative C-C bond formation using quinone-based chloranil/H+ reagent as the recyclable organic (metal-free) oxidant system to afford benzidines/naphthidines. Arylamines (3°/2°) designed with various substituents were employed to understand the steric as well as electronic preferences of oxidative dimerization, and a mechanism involving amine radical cation has been proposed. The tetraphenylbenzidine derivative obtained via oxidative C-C coupling has been further converted to blue-emissive hole-transporting material via a simple chemical transformation. This study highlights the preparation of novel HTMs in a simple, economic, and efficient manner.
- Maddala, Sudhakar,Mallick, Sudesh,Venkatakrishnan, Parthasarathy
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p. 8958 - 8972
(2017/09/11)
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- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
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Provided in the present invention are: a novel compound, capable of improving lifespan, stability, and light emitting efficiency of an element; an organic electrical element using the same; and an electronic device thereof. The compound is represented by chemical formula (1).COPYRIGHT KIPO 2016
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Paragraph 0405-0407
(2016/10/17)
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- Substituted carbazoles as hole transport materials for organic electroluminescence devices and organic electroluminescence devices comprising the same
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A hole transport material for an organic electroluminescence (EL) device, and an EL device including the same, the hole transport material being represented by Formula 1, below:
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Paragraph 0047-0049; 0050
(2016/04/20)
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- MONOAMINE MATERIAL FOR ORGANIC ELECTROLUMINESCENT DEVICE AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME
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A compound for an organic electroluminescence device and an organic electroluminescence device, the compound being represented by the following Chemical Formula 1:
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Paragraph 0075; 0077
(2017/01/12)
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- Method of manufacturing biaryl compd.
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PROBLEM TO BE SOLVED: To provide a technique to easily and effectively separate an aromatic halogen compound remaining in a biaryl compound. SOLUTION: This method for producing the biaryl compound comprises: reacting an aromatic boronic acid with the aromatic halogen compound, then adding a reducing agent to the reactant. COPYRIGHT: (C)2013,JPO&INPIT
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Paragraph 0036-0043; 0046
(2018/02/08)
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- ORGANIC ELECTRONIC ELEMENT USING A COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, AND AN ELECTRONIC DEVICE THEREOF
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Provided in the present invention are an organic electronic element using a compound which can improve light emitting efficiency, stability, and life of the element, and an electronic device thereof. The organic electronic device includes: a first electrode; a second electrode; and an organic substance layer located between the first electrode and the second electrode and including at least hole transfer layer and auxiliary light emitting layer, wherein the hole transfer layer includes a compound presented by chemical formula 1, and the auxiliary light emitting layer includes at least one among compounds presented by chemical formula 2 to 4.(110) Substrate(120) Positive electrode(130) Hole injection 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 electrodeCOPYRIGHT KIPO 2015
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- Hole transport material for organic electroluminescence device and organic electroluminescence device using the same
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A hole transport material for the organic electroluminescence device, the hole transport material being represented by the following Formula 1,
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Page/Page column 17; 19
(2015/11/09)
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- METHOD FOR PRODUCING TRIARYLAMINE COMPOUND
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[Problem] To provide a method for producing a triarylamine compound in which the reaction can be attained under a practical condition, the purification operation after the reaction is simple, the environmental burden is reduced and the production efficiency is high. [Means for Resolution] A method for producing a triarylamine compound through amination of a diarylamine compound and an aryl halide, wherein a catalyst comprising a salt of an imidazolium derivative represented by the following general formula (1) and a palladium compound is used, as combined with a base and a solvent to coexist therein.
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(2010/04/23)
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- Organic light-emitting devices consisting of N-triarylamine-based hole injecting/transporting materials
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A series of N-triarylamine-based derivatives such as 4,4'-bis[N-(1- naphthyl)-N-phenyl-amino]biphenyl (-NPD), 1,3,5-tris[4-(3-methylphenyl(phenyl) amino)phenyl]benzene (m-MTDAPB) and 1,3,5-tris-{4-[1-naphthyl(phenyl)amino] phenyl}benzene (1-TNAPB) were sy
- Cho, Ho Young,Park, Lee Soon,Han, Yoon Soo,Kwon, Younghwan,Ham, Jae-Yong
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scheme or table
p. 314 - 322
(2009/07/17)
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- Organic EL devices and production process thereof
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An organic electroluminescent device comprising a light-emitting layer between a pair of electrodes, the light-emitting layer comprising a mixture of a hole-transporting material consisting of a tertiary amine compound, an electron-transporting material and a light-emitting additive material, in which the tertiary amine compound has two or more oxidation potentials determined by a cyclic voltammetry wherein a potential difference between the first oxidation potential and the second oxidation potential in the oxidation potentials is 0.22V or more, and a glass transition temperature of at least 100° C., and the electron-transporting material has a glass transition temperature of at least 100° C.
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(2008/06/13)
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- TETRAMINE COMPOUND AND ORGANIC EL DEVICE
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The present invention provides a tetramine compound represented by the following general formula (1): wherein R1, R2 and R3, which may be the same or different, each represents a hydrogen atom, a tertiary alkyl group having 4 to 8 carbon atoms, an unsubstituted aryl group or an aryl group substituted with a tertiary alkyl group having 4 to 8 carbon atoms, and n represents 3 or 4. According to the invention, there can be provided a material suitable as a material for an organic EL element requiring luminous stability at the time of high temperature driving which has been the largest problem of the conventional organic EL element. Further, an organic EL element containing the above-mentioned tetramine compound and a method for producing the above-mentioned tetramine compound are also disclosed.
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Page/Page column 14-15
(2008/06/13)
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- TRIARYLAMINE DIMER DERIVATIVE HAVING AMORPHOUS PHASE AND METHOD FOR PRODUCING THE SAME
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PROBLEM TO BE SOLVED: To provide a triarylamine dimer derivative having amorphous phase, having high solubility to organic solvent without introducing any long-chain aliphatic substituent and capable of forming thin film by a simple method such as coating or spin coating one. SOLUTION: The triarylamine dimer derivative is represented by formula 1 [wherein, Ar1 to Ar4 are each a (substituted) aryl; R1 and R2 are each H, an alkyl, alkoxy or halogen atom; m and n are each 0-4; wherein Ar1 and Ar2 and Ar3 and Ar4 may be bound to each other to form a nitrogen atom-containing cyclic structure, respectively] and shows amorphous phase by its powder X-ray diffraction spectrum.
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Page/Page column 11
(2008/06/13)
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- Triarylamine dimer derivative having amorphous phase
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A triarylamine dimer derivative is represented by the following chemical formula [1] ???(in the chemical formula [1]: -Ar1, -Ar2, -Ar3 and -Ar4 are aryl groups being to have a substitutional group respectively, -R1 and -R2 are same or different to each other and one thereof is selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxyl group and a halogen atom; m and n are from 0 to 4; and with a proviso that -Ar1 and -Ar2, -Ar3 and -Ar4 are being to bind respectively to compose a cyclic structure group having a nitrogen atom) having an amorphous phase indicated by spectrum of powder X-ray diffractometry. The triarylamine dimer derivative is used for a charge transport material, an electrophotographic photosensitive conductor having thereof, an electroluminescence elemental device having a hole transport material thereof.
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Page/Page column 12
(2008/06/13)
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- Palladium catalysed aryl amination reactions in supercritical carbon dioxide
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Palladium catalysed C-N bond formation in supercritical carbon dioxide has been accomplished. Carbamic acid formation is avoided in part through the use of an N-silylamine as the coupling partner. Employing a catalyst system of Pd 2dba3 (1 mol%) and 2-dicyclohexylphosphino-2′, 4′,6′-triisopropyl-1,1′-biphenyl (X-Phos) (2 mol%) enabled the catalytic amination of aryl bromides and chlorides with N-silylanilines to be realised in excellent yield. Extension of the methodology to the N-arylation of N-silyldiarylamines, N-silylazoles and N-silylsulfonamides is reported. The Royal Society of Chemistry 2005.
- Smith, Catherine J.,Tsang, Melanie W.S.,Holmes, Andrew B.,Danheiser, Rick L.,Tester, Jefferson W.
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p. 3767 - 3781
(2007/10/03)
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- Process for preparing triarylamine dimer
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The present invention intends to provide a simple process for preparing triarylamine dimer without using any expensive chemicals, the process being able to achieve high reaction yield and being advantageous to be carried out on an industrial scale. The present invention provides a process for preparing triarylamine dimer (I) using the Ullmann reaction represented by the scheme: wherein X represents a halogen atom, R1and R2represent independently a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom, Ar represents a phenylene group, or a naphthylene group, characterized in that the reaction accelerator is polyethylene glycol or di- or monoalkyl ether of polyethylene glycol.
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- Anodic oxidation of novel hole-transporting materials derived from tetraarylbenzidines. Electrochemical and spectroscopic characterization
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Fluorenylidene-linked triarylamines, potential hole-transporting materials, have been prepared by the palladium-catalyzed Hartwig-Buchwald animation. Their redox and spectral properties were investigated in solution, applying cyclic voltammetry, UV-VIS and WR spectroscopy, and in situ spectroelectrochemical measurements. N,N,N′,N′-Tetraphenylbenzidine (1), N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (2), and triphenylamine (3) served as model substances in the study of the synthesized complex compounds 4 and S. In structure 4, two triphenylamine centres are linked with a non-conjugated fluorene bridge; in structure 5, two tetraarylbenzidine skeletons with two nitrogens are linked with a conjugated biphenyl-bridge system. In addition, structure 5 contains a non-conjugated fluorene bridge. The presence of the fluorene moiety in the molecular design has a significant influence on the investigated properties of the new materials. In the anodic oxidation of the tetraarylbenzidine-type compounds (1, 2, and 5), two well-defined reversible oxidation peaks were observed. However, the oxidation of the triphenylamine-type structures (3 and 4) is more complex, due to fast consecutive reactions. The dimer-like structures (4 and 5) are characterized by two independent oxidation centres that are simultaneously oxidized at approximately the same potentials. This was confirmed by quantitative cyclovoltammetric as well as UV-VIS investigations.
- Faber, Rene,Mielke, G. Felix,Rapta, Peter,Stasko, Andrej,Nuyken, Oskar
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p. 1403 - 1418
(2007/10/03)
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