- Arylamine-based organic compound and organic electroluminescent device containing same
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The invention relates to the technical field of semiconductor materials, in particular to an arylamine organic compound and an organic electroluminescent device containing the same. The structure of the compound is shown in the general formula (I). The ar
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Paragraph 0236-0238
(2021/09/21)
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- Organic compound, electronic component and electronic device
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The invention belongs to the technical field of organic materials, and provides an organic compound, an electronic component and an electronic device. The organic compound has the structure shown in the formula 1, in the formula 1, ring A is a fused aromatic ring with the carbon atom number being 10-14, and ring B is a benzene ring or a fused aromatic ring with the carbon atom number being 10-14; the organic compound of the present invention can improve the performance of an electronic device.
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Paragraph 0143-0146; 0147-0148; 0151
(2021/11/19)
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- DIARYL AMINE COMPOUND AND METHOD FOR PRODUCING THE SAME
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The present invention relates to a process for the preparation of diaryl amine compounds. A compound represented by chemical formula 1, a compound represented by chemical formula 2, and a synthetic reagent in a solvent, the synthetic reagent being CsF, KF, 18 - crown -6, K. 2 CO3, [TBAT] The present invention relates to a process for the preparation of diaryl amine compounds comprising a material selected from the group consisting of a (tetrabutylammonium difluorotriphenylsilicate), TBAF (tetrabutylammonium fluoride) and combinations thereof. Chemical Formula 1. Chemical Formula 2. The diaryl amine compound can be synthesized under the absence of a transition metal to be used to synthesize diaryl amine compounds having various substituents.
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Paragraph 0218; 0242-0246
(2021/03/16)
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- Diamine derivative and organic electroluminescent device thereof
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The invention provides a diamine derivative and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials. The diamine derivative represented by Formula 1 contains 9 -fluorene-substituted carbazole functional group, and the hole transport region or cover layer of the organic electroluminescent device of the present invention contains the carbazole derivative of Formula 1. The diamine derivative represented by the formula 1 has better hole transport performance and stability, and the prepared organic electroluminescent device containing the diamine derivative of the formula 1 in the prepared hole transport region exhibits high luminous efficiency. A longer service life and is a lower driving voltage. In addition, the diamine derivative of the formula 1 is also a better cover layer material; the prepared cover layer contains the diamine derivative of the formula 1; the organic electroluminescent device has high luminous efficiency and long service life.
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Paragraph 0121-0122; 0130-0131; 0134-0136
(2021/12/07)
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- COMPOUND FOR ORGANIC ELECTRIC ELEMENT, ORGANIC ELECTRIC ELEMENT COMPRISING THE SAME AND ELECTRONIC DEVICE THEREOF
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Disclosed are an organic electronic element comprising: a compound represented by chemical formula 1; a first electrode; a second electrode; and an organic layer located between the first electrode and the second electrode, and an electronic device comprising the organic electronic element. By comprising the compound represented by chemical formula 1 in the organic layer, it is possible to lower a driving voltage, improve luminous efficiency, and expand lifespan of the organic electronic element.COPYRIGHT KIPO 2019
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Paragraph 0130; 0143-0146
(2019/06/04)
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- Transition-Metal-Free Diarylation of Isocyanates with Arynes
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A facile method for the transition-metal-free diarylation of isocyanates with arynes in the presence of cesium fluoride has been developed, which affords functionalized diaryl amines in moderate to excellent yields. This reaction has good functional group tolerance and provides excellent regioselectivity by utilizing a methoxy-substituted aryne precursor.
- Jang, Woo Cheol,Hwang, Dong Wook,Seo, Jeong Hoon,Ko, Haye Min
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supporting information
(2019/08/30)
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- Electron-Catalyzed Coupling of Magnesium Amides with Aryl Iodides
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An electron was found to catalyze the coupling of magnesium diarylamides with aryl iodides giving triarylamines through a radical-anion intermediate. The transformation requires no transition metal catalysts or additives, and a wide array of products are formed in good-to-excellent yields.
- Kiriyama, Kazuya,Okura, Keisho,Tamakuni, Fumiko,Shirakawa, Eiji
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supporting information
p. 4519 - 4522
(2018/03/13)
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- PdCl2(Ph3P)2/Salicylaldimine Catalyzed Diarylation of Anilines with Unactivated Aryl Chlorides
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Triphenylphosphine and salicylaldimine could be used as a mixed ligand system to obtain a high catalytic activity for palladium catalyzed diarylation of primary anilines with unactivated aryl chlorides by the synergistic effect of ligands. The activity and selectivity of the catalytic system could be improved by modifying the structure of salicylaldimine. In refluxing o-xylene, PdCl2(Ph3P)2 with 2,5-ditrifluoromethyl N-phenylsalicylaldimine as a coligand shows high efficiency for the diarylation of various anilines. The catalytic system shows good toleration for the steric hindrance of the substrates. The facile catalytic system works as well on the multiple arylation of 1,1′-biphenyl- 4,4′-diamine with aryl chlorides to afford N,N,N′,N′-tetraaryl-1,1′-biphenyl-4,4′-diamines which are important intermediates of organic light emitting diode (OLED) hole transport materials.
- Tao, Xiaochun,Li, Lei,Zhou, Yu,Qian, Xuanying,Zhao, Min,Cai, Liangzhen,Xie, Xiaomin
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supporting information
p. 1749 - 1754
(2017/10/06)
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- Photochemical Synthesis of Complex Carbazoles: Evaluation of Electronic Effects in Both UV- and Visible-Light Methods in Continuous Flow
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An evaluation of both a visible-light- and UV-light-mediated synthesis of carbazoles from various triarylamines with differing electronic properties under continuous-flow conditions has been conducted. In general, triarylamines bearing electron-rich groups tend to produce higher yields than triarylamines possessing electron-withdrawing groups. The incorporation of nitrogen-based heterocycles, as well as halogen-containing arenes in carbazole skeletons, was well tolerated, and often synthetically useful complementarity was observed between the UV-light and visible-light (photoredox) methods.
- Hernandez-Perez, Augusto C.,Caron, Antoine,Collins, Shawn K.
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supporting information
p. 16673 - 16678
(2015/11/09)
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- Method for producing hydroxytriarylamine (by machine translation)
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PROBLEM TO BE SOLVED: To economically provide arylamines such as triarylamine. SOLUTION: An arylamine compound represented by formula (1) and an aryl compound having a leaving group represented by formula (2): X-Ar2-X1, are subjected to an arylamination reaction in the presence of a basic group, an alkaline metal salt and/or an alkaline earth metal salt, and an iron catalyst to thereby obtain arylamines such as triarylamines. In formula (1), Ar and Ar1are identical or different, and denote a substituted or non-substituted aryl group, and may be ring-condensed; and a denotes 1 or 2. In formula (2), X and X1are identical or different, and denote at least one leaving group selected from the group consisting of H or Br, I, CMs (mesylate), OTf (triflate) and OTs (tosylate), provided that X and X1are not simultaneously H, and have at least one leaving group; and Ar2denotes a substituted or non-substituted aryl group. COPYRIGHT: (C)2012,JPO&INPIT
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Paragraph 0034-0036
(2018/02/24)
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- Iron-catalyzed aromatic amination for nonsymmetrical triarylamine synthesis
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Novel iron-catalyzed amination reactions of various aryl bromides have been developed for the synthesis of diaryl- and triarylamines. The key to the success of this protocol is the use of in situ generated magnesium amides in the presence of a lithium halide, which dramatically increases the product yield. The present method is simple and free of precious and expensive metals and ligands, thus providing a facile route to triarylamines, a recurrent core unit in organic electronic materials as well as pharmaceuticals.
- Hatakeyama, Takuji,Imayoshi, Ryuji,Yoshimoto, Yuya,Ghorai, Sujit K.,Jin, Masayoshi,Takaya, Hikaru,Norisuye, Kazuhiro,Sohrin, Yoshiki,Nakamura, Masaharu
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supporting information
p. 20262 - 20265
(2013/02/23)
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- Copper-catalyzed synthesis of triarylamines from aryl halides and arylamines
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A simple and efficient methodology for the synthesis of triphenylamines has been demonstrated using copper catalyst with a ligand and tripotassium phosphate as the base. The effect of parameters such as catalyst precursors, ligands, bases and solvents were studied and a series of triphenylamines were obtained with moderate to excellent yields in DMF. This reaction displays great functional groups compatibility in the presence of a broad range of functional groups.
- Qian, Cunwei,Xu, Shaojie,Zong, Qianshou,Fang, Dong
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p. 1881 - 1885
(2012/10/29)
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- Pyridine-catalyzed double C-N coupling reaction of an isocyanate with two benzynes
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A pyridine-catalyzed double C-N bond cross-coupling reaction involving two benzynes with an isocyanate was carried out. The coupling reaction proceeded through a unique pathway involving the formation of an unstable carbamic acid intermediate and facile decarboxylation. Subsequent nucleophilic addition/protonation of in situ prepared amines with benzynes afforded variously substituted diaryl- and triarylamines in moderate to good yields with tolerance of a variety of functional groups. Copyright
- Lee, Yi-Hsien,Chen, Yen-Chung,Hsieh, Jen-Chieh
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supporting information; experimental part
p. 247 - 250
(2012/02/04)
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- NOVEL COMPOUND AND ORGANIC ELECTRONIC DEVICE USING SAME
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The present invention relates to a novel compound and an organic light emitting device using the compound, and the compound according to the present invention may largely improve a life span, efficiency, electrochemical stability and thermal stability of the organic light emitting device.
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Page/Page column 36
(2011/08/03)
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- Nickel-catalyzed cross-coupling of diarylamines with haloarenes
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The cross-coupling reaction of diarylamines with aryl bromides/iodides can be effected by the Ni(ii)-(σ-aryl) complex/PPh3/NaH system, and a preliminary investigation was conducted into the mechanism of this reaction.
- Gao, Cai-Yan,Cao, Xingbo,Yang, Lian-Ming
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supporting information; experimental part
p. 3922 - 3925
(2009/12/06)
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- Evaluation of aromatic amination catalyzed by palladium on carbon: A practical synthesis of triarylamines
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A heterogeneous palladium on carbon (Pd/C)-catalyzed coupling between amines and aromatic halides including aromatic chlorides has been achieved using sodium tert-butoxide (NaO-t-Bu) and 1,1′-bis(diphenylphosphino)ferrocene (dppf) as a ligand in cyclopentyl methyl ether (CPME). The use of potassium tert-butoxide (KO-t-Bu) in place of NaO-t-Bu brought about the benzyne-mediated aromatic amination even without Pd/C and dppf, giving a mixture of regioisomers when 4-substituted bromobenzenes were employed as the substrate. The combination of Pd/C, dppf, NaO-t-Bu could be utilized for the syntheses of a broad range of triarylamines by replacing CPME with mesitylene which can provide a higher reaction temperature. The Pd/C could be quantitatively recovered and reused until at least the fourth cycle without any loss in catalytic activity. The quite low leaching of palladium (1.1%) was demonstrated by an inductively coupled plasma-atomic emission spectrometric analysis.
- Monguchi, Yasunari,Kitamoto, Katsunori,Ikawa, Takashi,Maegawa, Tomohiro,Sajiki, Hironao
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supporting information; experimental part
p. 2767 - 2777
(2009/12/08)
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- NEW DIAMINE DERIVATIVES AND ORGANIC ELECTRONIC DEVICE USING THE SAME
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The present invention relates to a new diamine derivative, and an organic electronic device using the same. The diamine derivative according to the present invention can serve as a hole injecting, hole transporting, electron injecting, electron transporting, or light emitting material in an organic electronic device including an organic light emitting device. Particularly, it can serve as a light emitting dopant as used alone, in particular, a blue light emitting dopant. The organic electronic device according to the present invention exhibits excellent characteristics in terms of efficiency, drive voltage, life time, and stability.
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Page/Page column 53-54
(2008/12/08)
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- Arylation of diarylamines catalyzed by Ni(II)-PPh3 system
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(Chemical Equation Presented) The cross-coupling of bromomagnesium diarylamides, generated in situ from diarylamines, with aryl bromides or iodides can be effected with a simple NiCl2(PPh3) 2-PPh3 catalyst system under relatively mild conditions. This coupling reaction is an inexpensive, convenient, and practical method, functioning as an alternative to the corresponding Pd-catalyzed or Cu-mediated process for the synthesis of triarylamines.
- Chen, Chen,Yang, Lian-Ming
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p. 2209 - 2211
(2007/10/03)
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- Phase-Transfer Catalysis in the Ullmann Synthesis of Substituted Triphenylamines
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A variety of substituted triphenylamine derivatives were prepared in nearly quantitative yields by the use of 18-crown-6 as a phase transfer catalyst under the Ullmann reaction conditions.
- Gauthier, Sylvie,Frechet, Jean M. J.
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p. 383 - 385
(2007/10/02)
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- 13C NMR Study of ortho-, meta- and para-Substituted Phenylhiphenylamines: Substituent Effect Correlations
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The 13C chemical shifts of 11 substituted triphenylamines have been determined and the assignment of these resonances made using intensities, 1H and 19F couplings and predictions from bond additivity relationships. 13C chemical shifts at carbons bearing the substituent and at carbons ortho to the substituent correlated reasonably well with the Q parameter.A multiple regression analysis of chemical shifts with the field and resonance parameters of Swain and Lupton and the Q parameter produced significantly better correlations than those obtained when Q was omitted for these positions. 13C chemical shift correlations for carbons meta and para to the substituent were not significantly better than when Q was omitted.Significant correlations were obtained between field and resonance parameters and 13C chemical shifts of C-o and C-p, and C-i, C-o, C-m and C-p of the non-substituent bearing phenyl rings in ortho- and para-substituted phenyldiphenylamines, respectively.
- Grimley, Eugene,Collum, David H.,Alley, Earl G.,Layton, Bobby
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p. 296 - 302
(2007/10/02)
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