N⁴,N⁴,N^4',N^4'-tetra-m-tolyl-[1,1'-biphenyl]-4,4'-diamine | 106614-54-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N⁴,N⁴,N^4',N^4'-tetra-m-tolyl-[1,1'-biphenyl]-4,4'-diamine
• 英文别名: N,N,N',N'-tetrakis(4-methylphenyl)(1,1'-biphenyl)-4,4'-diamine；4,4'-bis[4-(di-m-tolyl)amino]benzidine；4,4'-bis[N-(3-methylphenyl)-N-phenylamino]biphenyl；N,N,N',N'-Tetrakis(3-methylphenyl)-benzidine；3-methyl-N-[4-[4-(3-methyl-N-(3-methylphenyl)anilino)phenyl]phenyl]-N-(3-methylphenyl)aniline
• CAS: 106614-54-4
• 化学式: C₄₀H₃₆N₂
• 分子量: 544.739
• InChiKey: ARRHCLZWLCVLRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-溴甲基苯 、 联苯胺 在 bis-triphenylphosphine-palladium(II) chloride 、 三苯基膦 、 sodium t-butanolate 作用下， 以 邻二甲苯 为溶剂， 反应 48.0h， 以90%的产率得到N⁴,N⁴,N^4',N^4'-tetra-m-tolyl-[1,1'-biphenyl]-4,4'-diamine
  参考文献：
  名称：

  Effects of solvent and base on the palladium-catalyzed amination: PdCl2(Ph3P)2/Ph3P-catalyzed selective arylation of primary anilines with aryl bromides

  摘要：

  A readily accessible catalytic system, PdCl2(Ph3P)(2)/Ph3P, was developed for the selective arylation of primary anilines with aryl bromides. The strong influence of solvents and bases on the catalytic activity was observed. In refluxing o-xylene, triphenylphosphine shows high efficiency for Pd-catalyzed intermolecular amination reactions. By changing the bases, mono- and diarylation of primary amines could be selectively achieved in high yields. Moreover, the catalytic system showed good toleration for the steric hindrance of anilines. A series of N,N,N',N'-tetraaryl-1,1'-biphenyl-4,4'-diamines, important intermediates of OLED hole transport materials, were synthesized facilely via coupling reactions between 4,4'-diaminobiphenyls and aryl bromides. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.048

文献信息

• Metal-Free Oxidative C–C Coupling of Arylamines Using a Quinone-Based Organic Oxidant
  作者：Sudhakar Maddala、Sudesh Mallick、Parthasarathy Venkatakrishnan

  DOI：10.1021/acs.joc.7b01377

  日期：2017.9.1

  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

  使用基于醌的氯腈/ H +试剂作为可循环使用的有机（无金属）氧化剂体系，可以显示出多种芳基胺进行氧化C-C键形成，以提供联苯胺/萘啶。设计了具有各种取代基的芳胺（3°/ 2°）用于理解氧化二聚作用的空间和电子偏好，并提出了涉及胺自由基阳离子的机理。通过氧化CC偶联获得的四苯基联苯胺衍生物已通过简单的化学转化进一步转化为发射蓝色光的空穴传输材料。这项研究强调了以简单，经济和有效的方式准备新型HTM。
• PdCl₂(Ph₃P)₂/Salicylaldimine Catalyzed Diarylation of Anilines with Unactivated Aryl Chlorides
  作者：Xiaochun Tao、Lei Li、Yu Zhou、Xuanying Qian、Min Zhao、Liangzhen Cai、Xiaomin Xie

  DOI：10.1002/cjoc.201700276

  日期：2017.11

  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

  三苯基膦和水杨醛亚胺可以用作混合的配体体系，以通过配体的协同作用获得钯催化的伯苯胺与未活化的芳基氯的二芳基化的高催化活性。通过改变水杨醛亚胺的结构可以提高催化体系的活性和选择性。在回流的ø二甲苯，的PdCl 2（PH 3 P）2与2,5- ditrifluoromethyl Ñ苯基水杨醛亚胺大肠菌素对各种苯胺的二芳基化反应显示出很高的效率。催化体系对底物的空间位阻表现出良好的耐受性。简便的催化体系在1,1'-联苯-4,4'-二胺与芳基氯的多重芳基化反应中也能提供N，N，N'，N'-四芳基-1,1'-联苯-4 ，4'-二胺是有机发光二极管（OLED）空穴传输材料的重要中间体。
• ALUMINUM CHELATE COMPLEX FOR ORGANIC EL MATERIAL
  申请人：MATSUO Shinji

  公开号：US20100256377A1

  公开（公告）日：2010-10-07

  This invention provides an organic EL material useful for the emissive layer of an organic EL element which deteriorates little in luminance when operated over a prolonged period of time and shows excellent durability. The material is an aluminum chelate complex which is represented by general formula (1) in which Ar 1 is a mono- or bicylic arylene group, Ar 2 is a mono- or bicyclic aryl group, R 1 -R 6 are hydrogen or hydrocarbon groups containing 1-8 carbon atoms and contains a compound represented by general formula (1) in which Ar 2 is a halogen as an impurity in an amount of 350 wt ppm or less.

  这项发明提供了一种有机EL材料，适用于有机EL元件的发射层，在长时间运行时，其亮度几乎不会退化，并且具有出色的耐久性。该材料是一种铝螯合物复合物，其由一般式（1）表示，其中Ar1是单环或双环芳烃基团，Ar2是单环或双环芳基团，R1-R6是含有1-8个碳原子的氢或烃基团，并且含有一种以卤素为杂质的化合物，其以350重量ppm或更少的量表示。
• Polymerizable, luminescent compounds and mixtures, luminescent polymer materials and their use
  申请人：Poetsch Eike

  公开号：US20050244718A1

  公开（公告）日：2005-11-03

  The invention relates to new polymerizable, luminescent compounds of formula I wherein R 1 , R 2 , A 1 , A 2 , A 3 , Z 1 , W and Q have the meanings given in claim 1. Furthermore the invention relates to polymerizable mixtures containing compounds according to the invention and pleferably at least one polymerizable mesogenic compound. Polymer materials obtainable by polymerizing such mixtures are also described. These compounds, mixtures and materials show advantageous photoluminescent and/or electroluminescent properties and may be used in light emitting devices and optical- or electrooptical display elements.

  本发明涉及公式I的新型可聚合、发光化合物，其中R1、R2、A1、A2、A3、Z1、W和Q的含义如权利要求书所述。此外，本发明还涉及含有本发明化合物的可聚合混合物，优选地至少包含一种可聚合中间相化合物。还描述了通过聚合这种混合物获得的聚合材料。这些化合物、混合物和材料具有有利的光致发光和/或电致发光性能，并可用于发光装置和光学或电光显示元件。
• Aluminum chelate complex for organic el material
  申请人：Matsuo Shinji

  公开号：US20070054148A1

  公开（公告）日：2007-03-08

  This invention provides an organic EL material useful for the emissive layer of an organic EL element which deteriorates little in luminance when operated over a prolonged period of time and shows excellent durability. The material is an aluminum chelate complex which is represented by general formula (1) in which Ar 1 is a mono- or bicylic arylene group, Ar 2 is a mono- or bicyclic aryl group, R 1 —R 6 are hydrogen or hydrocarbon groups containing 1-8 carbon atoms and contains a compound represented by general formula (1) in which Ar 2 is a halogen as an impurity in an amount of 350 wt ppm or less.

  本发明提供了一种有机EL材料，可用于有机EL元件的发光层，该材料在长时间运行时发光度几乎不会降低，并表现出优异的耐久性。该材料是一种铝螯合物复合物，其由一般式（1）表示，其中Ar1是单环或双环芳基烃基，Ar2是单环或双环芳基基团，R1-R6是含有1-8个碳原子的氢或碳氢基团，并且含有一种以卤素为杂质的化合物，其量为350重量ppm或以下。