N,N'-diphenyl-N-(1-naphthyl)benzidine | 352359-41-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N'-diphenyl-N-(1-naphthyl)benzidine
• 英文别名: N-(1-Naphthyl)-N,N'-diphenylbenzidine；4-(N-phenyl-N-1-naphthylamino)-biphenyl-N'-phenylamine；4-(N-phenyl-N-naphthylamino)-biphenyl-N'-phenylamine；N,N'-diphenyl-N-naphth-1-ylbenzidine；N,N'-diphenyl-N-1-naphthylbenzidine；N-[4-(4-anilinophenyl)phenyl]-N-phenylnaphthalen-1-amine
• CAS: 352359-41-2
• 化学式: C₃₄H₂₆N₂
• 分子量: 462.594
• InChiKey: QWODREODAXFISP-UHFFFAOYSA-N

物化性质

• 沸点：
  662.0±48.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N'-diphenyl-N-(1-naphthyl)benzidine 在 tris(dibenzylideneacetone)dipalladium (0) 三叔丁基膦 、 四丁基氟化铵 、 氢化钾 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 30.0h， 生成 N-(1-naphthyl)-N,N'-diphenyl-N'-(4-((4-vinylphenyl)methoxymethyl)phenyl)benzidine
  参考文献：
  名称：

  Synthesis and Characterization of Photo-Cross-Linkable Hole-Conducting Polymers

  摘要：

  The synthesis and characterization of side-chain polymers functionalized with hole-transporting units and photo-cross-linkable groups, which can be used for solution-based preparation of multilayer organic light-emitting devices (OLEDs), are discussed. The concept deals with triarylamine and oxetane-functionalized styrenes, which are copolymerized by radical polymerization. Four different types of hole-transporting monomers were combined with one cross-linkable monomer in two different ratios, yielding two groups of each four polymers (P1A...P4A and P1B...P4B). The polymers were investigated by NMR spectroscopy, molecular weights were determined by GPC with light scattering, and the thermal properties were measured with differential scanning calorimetry (DSC). Optical characterization by UV-vis and fluorescence spectroscopy was performed. Electrochemical and cross-linking characteristics of the copolymers were investigated to proove this strategy's potential in application for modern multilayer polymer OLEDs. Finally, hole-only devices were prepared for evaluation of the semiconductive performance of the materials.

  DOI：

  10.1021/ma048365h
• 作为产物：
  描述：

  N-苯基-1-萘胺 在 tris(dibenzylideneacetone)dipalladium (0) 1,1'-双(二苯基膦)二茂铁 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 13.0h， 生成 N,N'-diphenyl-N-(1-naphthyl)benzidine
  参考文献：
  名称：

  Synthesis and Characterization of Photo-Cross-Linkable Hole-Conducting Polymers

  摘要：

  The synthesis and characterization of side-chain polymers functionalized with hole-transporting units and photo-cross-linkable groups, which can be used for solution-based preparation of multilayer organic light-emitting devices (OLEDs), are discussed. The concept deals with triarylamine and oxetane-functionalized styrenes, which are copolymerized by radical polymerization. Four different types of hole-transporting monomers were combined with one cross-linkable monomer in two different ratios, yielding two groups of each four polymers (P1A...P4A and P1B...P4B). The polymers were investigated by NMR spectroscopy, molecular weights were determined by GPC with light scattering, and the thermal properties were measured with differential scanning calorimetry (DSC). Optical characterization by UV-vis and fluorescence spectroscopy was performed. Electrochemical and cross-linking characteristics of the copolymers were investigated to proove this strategy's potential in application for modern multilayer polymer OLEDs. Finally, hole-only devices were prepared for evaluation of the semiconductive performance of the materials.

  DOI：

  10.1021/ma048365h

文献信息

• Use of Rylene Derivatives as Photosensitizers in Solar Cells
  申请人：Pschirer Neil Gregory

  公开号：US20080269482A1

  公开（公告）日：2008-10-30

  Use of rylene derivatives I with the following definition of the variables: X together both —COOM; Y a radical -L-NR 1 R 2 (y1) -L-Z-R 3 (y2) the other radical hydrogen; together both hydrogen; R is optionally substituted (het)aryloxy, (het)arylthio; P is —NR 1 R 2 ; B is alkylene; optionally substituted phenylene; combinations thereof; A is —COOM; —SO 3 M; —PO 3 M 2 ; D is optionally substituted phenylene, naphthylene, pyridylene; M is hydrogen; alkali metal cation; [NR 5 ] 4 + ; L is a chemical bond; optionally indirectly bonded, optionally substituted (het)arylene radical; R 1 , R 2 are optionally substituted (cyclo)alkyl, (het)aryl; together optionally substituted ring comprising the nitrogen atom; Z is —O—; —S—; R 3 is optionally substituted alkyl, (het)aryl; R′ is hydrogen; optionally substituted (cyclo)alkyl, (het)aryl; R 5 is hydrogen; optionally substituted alkyl (het)aryl; m is 0, 1, 2; n, p m=0: 0, 2, 4 where: n+p=2, 4, if appropriate 0; m=1: 0, 2, 4 where: n+p=0, 2, 4; m=2: 0, 4, 6 where: n+p=0, 4, 6, or of mixtures thereof as photosensitizers in solar cells.

  使用以下变量定义的莱伦衍生物I的用途： X一起 两者都是-COOM; Y是一个基团 -L-NR 1 R 2 (y1) -L-Z-R 3 (y2) 另一个基团是氢; 一起 两者都是氢; R可选择地被取代为(het)芳氧基，(het)芳基硫基; P是-NR 1 R 2 ; B是烷基; 可选择地被取代的苯基; 它们的组合; A是-COOM; -SO 3 M; -PO 3 M 2 ; D可选择地被取代为苯基，萘基，吡啶基; M是氢; 碱金属阳离子; [NR 5 ] 4 + ; L是化学键; 可选择地间接键合，可选择地被取代的(het)芳基基团; R 1 ，R 2 可选择地被取代的(环)烷基，(het)芳基; 一起可选择地被取代的环，其中包括氮原子; Z是-O-; -S-; R 3 可选择地被取代的烷基，(het)芳基; R′是氢; 可选择地被取代的(环)烷基，(het)芳基; R 5 是氢; 可选择地被取代的烷基(het)芳基; m为0, 1, 2; n, p, m=0: 0, 2, 4其中：n+p=2, 4，如果适用为0; m=1: 0, 2, 4其中：n+p=0, 2, 4; m=2: 0, 4, 6其中：n+p=0, 4, 6， 或者作为太阳能电池中的光敏剂的混合物。
• AROMATIC AMINE DERIVATIVES AND ELECTROLUMINESCENCE DEVICE USING THE SAME
  申请人：Kawamura Masahiro

  公开号：US20070029927A1

  公开（公告）日：2007-02-08

  An aromatic amine derivative with a specific structure and an organic electroluminescence device which comprises at least one organic thin film layer comprising a light emitting layer sandwiched between a pair of electrode consisting of an anode and a cathode, wherein at least one of the organic thin film layer comprises the aromatic amine derivative singly or as its mixture component. The organic electroluminescence device which exhibits an enhanced current efficiency of light emission and emits blue light with a prolonged lifetime is realized.

  一种具有特定结构的芳香胺衍生物和一种有机电致发光器件，该器件至少包括一个有机薄膜层，其中包括夹在由阳极和阴极组成的一对电极之间的发光层，其中至少一个有机薄膜层包括该芳香胺衍生物单独或作为其混合组分。实现了一种具有增强的发光电流效率并且发出蓝光并具有延长寿命的有机电致发光器件。
• COMPOUNDS AND ORGANIC LIGHT EMITTING DIODE USING THE SAME
  申请人：Jeon Byung-Sun

  公开号：US20100065827A1

  公开（公告）日：2010-03-18

  Disclosed are new compounds and an organic light emitting diode using the same. The organic light emitting diode using the new compound according to the present invention exhibits excellent characteristics in terms of actuating voltage, light efficiency, and lifespan.

  本发明公开了新化合物及其所使用的有机发光二极管。根据本发明所使用的新化合物的有机发光二极管在驱动电压、光效率和寿命方面表现出优异的特性。
• Anodic Oxidation of Novel Hole-Transporting Materials Derived from Tetraarylbenzidines. Electrochemical and Spectroscopic Characterization
  作者：René Fáber、G. Felix Mielke、Peter Rapta、Andrej Staško、Oskar Nuyken

  DOI：10.1135/cccc20001403

  日期：——

  Fluorenylidene-linked triarylamines, potential hole-transporting materials, have been prepared by the palladium-catalyzed Hartwig-Buchwald amination. Their redox and spectral properties were investigated in solution, applying cyclic voltammetry, UV-VIS and EPR 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 5. 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.

  通过钯催化的Hartwig-Buchwald胺化反应，制备了荧基亚甲基三芳胺类化合物，这些化合物具有潜在的空穴传输材料的特性。采用循环伏安法、紫外-可见光谱和电子顺磁共振光谱以及原位光谱电化学测量，研究了它们在溶液中的氧化还原和光谱性质。在合成的复杂化合物4和5的研究中，N，N，N'，N'-四苯基苯胺（1）、N，N'-二（1-萘基）-N，N'-二苯基苯胺（2）和三苯胺（3）作为模型物质。在结构4中，两个三苯胺中心通过一个非共轭的荧烯桥连接；在结构5中，两个带有两个氮原子的四苯基苯胺骨架通过一个共轭的联苯桥系统连接。此外，结构5含有一个非共轭的荧烯桥。分子设计中荧烯基团的存在对新材料的研究性质有显著影响。在四苯基苯胺类化合物（1、2和5）的阳极氧化中，观察到两个明确定义的可逆氧化峰。然而，三苯胺类结构（3和4）的氧化更为复杂，由于快速连续反应。类似二聚体的结构（4和5）具有两个独立的氧化中心，同时在大约相同的电位上被氧化。这得到了定量的循环伏安和紫外-可见光谱研究的证实。
• AROMATIC TRIAMINE COMPOUND AND ORGANIC ELECTTROLUMINESCENCE DEVICE USING THE SAME
  申请人：KAWAMURA Masahiro

  公开号：US20090115320A1

  公开（公告）日：2009-05-07

  Provided are an aromatic triamine compound of a specific structure having at least one terphenyl structure and an organic electroluminescence device in which an organic thin film layer comprising a single layer or plural layers having at least a luminescent layer is interposed between a cathode and an anode, wherein at least one layer of the above organic thin film layers contains the aromatic triamine compound described above in the form of a single component or a mixed component, and provided are the organic electroluminescence device having a high luminous efficiency and a long life and the novel aromatic triamine compound for materializing the same.

  提供了一种具有至少一个三苯基结构的特定结构的芳香性三胺化合物，以及一种有机电致发光装置，其中在阴极和阳极之间夹有包括至少一个发光层的单层或多层有机薄膜层，上述有机薄膜层中的至少一层以单一组分或混合组分的形式含有上述芳香性三胺化合物，提供了具有高发光效率和长寿命的有机电致发光装置和用于实现其的新型芳香性三胺化合物。