2-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenol | 94212-05-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenol
• 英文别名: 6-(1-Phenyl-1,3-dihydro-2H-benzimidazol-2-ylidene)cyclohexa-2,4-dien-1-one；2-(1-phenylbenzimidazol-2-yl)phenol
• CAS: 94212-05-2
• 化学式: C₁₉H₁₄N₂O
• 分子量: 286.333
• InChiKey: PMVRBPKKJNHTLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  三苯基硼烷 、 2-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenol 以 四氢呋喃 为溶剂， 反应 12.0h， 以70%的产率得到9,9,17-Triphenyl-8-oxa-17-aza-10-azonia-9-boranuidatetracyclo[8.7.0.02,7.011,16]heptadeca-1(10),2,4,6,11,13,15-heptaene
  参考文献：
  名称：

  2-(2-Hydroxyphenyl)benzimidazole-Based Four-Coordinate Boron-Containing Materials with Highly Efficient Deep-Blue Photoluminescence and Electroluminescence

  摘要：

  Two novel four-coordinate boron-containing emitters 1 and 2 with deep-blue emissions were synthesized by refluxing a 2-(2-hydroxyphenyl)benzimidazole ligand with triphenylborane or bromodibenzoborole. The boron chelation produced a new pi-conjugated skeleton, which rendered the synthesized boron materials with intense fluorescence, good thermal stability, and high carrier mobility. Both compounds displayed deep-blue emissions in solutions with very high fluorescence quantum yields (over 0.70). More importantly, the samples showed identical fluorescence in the solution and solid states, and the efficiency was maintained at a high level (approximately 0.50) because of the bulky substituents between the boron atom and the benzimidazole unit, which can effectively separate the flat luminescent units. In addition, neat thin films composed of 1 or 2 exhibited high electron and hole mobility in the same order of magnitude 10(-4), as determined by time-of-flight. The fabricated electroluminescent devices that employed 1 or 2 as emitting materials showed high-performance deep-blue emissions with Commission Internationale de L'Eclairage (CIE) coordinates of (X = 0.15, Y = 0.09) and (X = 0.16, Y = 0.08), respectively. Thus, the synthesized boron-containing materials are ideal candidates for fabricating high-performance deep-blue organic light-emitting diodes.

  DOI：

  10.1021/ic502815q
• 作为产物：
  描述：

  邻甲氧基苯甲酸 、 邻氨基二苯胺 以 邻二氯苯 为溶剂， 反应 40.0h， 以10%的产率得到2-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenol
  参考文献：
  名称：

  Novel metal–chelate emitting materials based on polycyclic aromatic ligands for electroluminescent devices

  摘要：

  我们设计并合成了基于多环芳烃配体的新型金属-螯合物复合物，用于电致发光器件。这些复合物表现出强烈的蓝色和绿色荧光。我们研究了使用这些复合物作为发光层的器件的电致发光特性。获得了几种良好的发光材料，并发现电致发光特性在很大程度上取决于配体的结构。

  DOI：

  10.1039/a803308k

文献信息

• [EN] ORGANIC ELECTRONIC DEVICE COMPRISING AN ORGANIC SEMICONDUCTOR LAYER<br/>[FR] DISPOSITIF ÉLECTRONIQUE ORGANIQUE COMPRENANT UNE COUCHE SEMI-CONDUCTRICE ORGANIQUE
  申请人：NOVALED GMBH

  公开号：WO2018215348A1

  公开（公告）日：2018-11-29

  The present invention relates to a compound of formula 1 and an organic electronic device comprising an organic semiconductor layer, wherein at least one organic semiconductor layer comprises a compound of formula (1), wherein L1 has the formula (2) and L2 has the formula (3), wherein L1 and L2 are bonded at "*" via a single bond independently to the same or different arylene groups or heteroarylenes group of Ar1; and wherein X1, X2 are independently selected from O, S and Se; Ar1 is selected from substituted or unsubstituted C20 to C52 arylene or C14 to C64 heteroarylene, wherein the substituent of the substituted C20 to C52 arylene or C14 to C64 heteroarylene are independently selected from C1 to C12 alkyl, C1 to C12 alkoxy, CN, halogen, OH, C6 to C25 aryl and C2 to C21 heteroaryl; R1, R2 are independently selected from substituted or unsubstituted C1 to C16 alkyl, wherein the substituent of substituted C1 to C16 alkyl is selected from C6 to C18 arylene or C2 to C12 heteroarylene; R3, R4 are independently selected from substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted C6 to C18 arylene, C2 to C20 heteroarylene, wherein the substituent of substituted C1 to C16 alkyl, the substituent of the substituted C6 to C18 arylene, C2 to C20 heteroarylene are independently selected from C6 to C18 arylene or C2 to C12 heteroarylene; n is selected from 1 to 5, wherein n is an integer number.

  本发明涉及一种化合物的化学式1和包括有机半导体层的有机电子器件，其中至少一个有机半导体层包括一个化合物的化学式（1），其中L1具有化学式（2），L2具有化学式（3），其中L1和L2通过单键独立地与Ar1的相同或不同的芳基或杂芳基通过“*”键合；其中X1、X2独立选择自O、S和Se；Ar1选择自取代或未取代的C20至C52芳基或C14至C64杂芳基，其中取代的C20至C52芳基或C14至C64杂芳基的取代基独立选择自C1至C12烷基、C1至C12烷氧基、CN、卤素、OH、C6至C25芳基和C2至C21杂芳基；R1、R2独立选择自取代或未取代的C1至C16烷基，其中取代的C1至C16烷基的取代基选择自C6至C18芳基或C2至C12杂芳基；R3、R4独立选择自取代或未取代的C1至C16烷基，取代或未取代的C6至C18芳基，C2至C20杂芳基，其中取代的C1至C16烷基、取代的C6至C18芳基、C2至C20杂芳基的取代基独立选择自C6至C18芳基或C2至C12杂芳基；n选择自1至5，其中n为整数。
• Conventional and Microwave-Assisted Synthesis of Benzimidazole Derivatives and Their<i>In Vitro</i>Inhibition of Human Cyclooxygenase
  作者：Daniela Secci、Adriana Bolasco、Melissa D'Ascenzio、Flavio della Sala、Matilde Yáñez、Simone Carradori

  DOI：10.1002/jhet.1058

  日期：2012.9

  A large series of 1,2‐diaryl‐benzimidazole and 2‐aryl‐1H‐benzimidazole derivatives were synthesized with slight differences using both microwave irradiation and conventional heating methods. Usually higher yields and time reactions reduction were obtained with the former method. All compounds were assayed for their in vitro ability to inhibit human cyclooxygenases, and most of them showed an encouraging

  使用微波辐照和常规加热方法合成了一系列1,2-二芳基-苯并咪唑和2-芳基-1 H-苯并咪唑衍生物，但略有差异。通常，使用前一种方法可获得更高的产率和时间反应的减少。分析了所有化合物在体外抑制人环氧化酶的能力，其中大多数在微摩尔范围内显示出令人鼓舞的抑制活性和同工型选择性。
• The effect of locking π-conjugation in organoboron moieties in the structures of luminescent tetracoordinate boron complexes
  作者：Mateusz Urban、Krzysztof Durka、Patrycja Górka、Gabriela Wiosna-Sałyga、Krzysztof Nawara、Piotr Jankowski、Sergiusz Luliński

  DOI：10.1039/c9dt01332f

  日期：——

  the spiro geometry of the boron atom, borafluorene and ligand units are perpendicularly aligned, which considerably affects the flexibility of the molecule as well as its solid-state structure. Through comparative analysis with close diphenyl analogues, we show how these structural features influence the thermal, photoluminescent and charge mobility behaviour of the studied compounds. Crystal structural

  为了阐明有机硼部分的刚性化对这些化合物的物理化学性质的影响，在实验和理论上对一系列的8种发光的硼芴配合物进行了广泛的研究。由于硼原子的螺线几何形状，硼芴和配体单元垂直排列，这极大地影响了分子的柔性及其固态结构。通过与紧密的二苯基类似物进行比较分析，我们显示了这些结构特征如何影响所研究化合物的热，光致发光和电荷迁移行为。晶体结构分析表明，这些分子主要通过垂直排列的硼芴与相邻分子的配体部分之间形成的C–H⋯O和C–H⋯π相互作用连接，分别充当电子密度的互补供体和受体。这也有效地防止了分子参与不利的π堆积接触。此外，结构分析表明，由于OBN杂环畸变和相互的硼芴-配体平面运动，硼硼烷络合物具有相当程度的柔韧性。这些效应的大小严格取决于配体结构，并可能导致相对于BPh的量子产率增加或降低 结构分析表明，由于OBN杂环畸变和相互之间的硼芴配体平面运动，硼芴配合物具有相当程度的灵活性。这些效应的大小严格
• Organic Semiconducting Material Comprising an Electrical n-Dopant and an Electron Transport Matrix and Electronic Device Comprising the Semiconducting Material
  申请人：Novaled GmbH

  公开号：US20180114921A1

  公开（公告）日：2018-04-26

  The present invention relates to an organic semiconducting material and to an electronic device comprising the semiconducting material, particularly to an electroluminescent device, particularly to an organic light emitting diode (OLED), wherein the semiconducting material comprises a first electron transport matrix compound and an electrical n-dopant; the invention pertains also to a device comprising the electric device and/or the electroluminescent device, particularly to a display device, particularly to a display device comprising the OLED.

  本发明涉及一种有机半导体材料以及包括该半导体材料的电子设备，特别是一种电致发光器件，特别是一种有机发光二极管（OLED），其中该半导体材料包括第一电子传输基质化合物和一种电子n-掺杂剂；该发明还涉及一种包括该电子设备和/或该电致发光器件的设备，特别是一种显示设备，特别是一种包括OLED的显示设备。
• Gas-phase generation and cyclisation reactions of imidoyl radicals
  作者：Rino Leardini、Hamish McNab、Daniele Nanni、Anton G. Tenan、Andrew Thomson

  DOI：10.1039/c1ob06228j

  日期：——

  Some 1,2-diarylimidoyl radicals were generated in the gas-phase by intramolecular radical translocation from ortho-imino-aryloxyl radicals, in turn generated under flash vacuum pyrolysis (FVP) conditions. The imidoyls reacted with XRortho′-substituents in the N-aryl group to give (in most cases) modest yields of cyclisation products. Depending on the nature of the bridging atom (X), the formation of

  在气相中，通过邻亚氨基亚氨基芳基氧基的分子内基团易位而在气相中产生了一些1，2-二芳基酰亚胺基，然后在快速真空热解（FVP）条件下产生了该基团。亚胺基与N-芳基中的XR邻位取代基反应（在大多数情况下）产生适量的环化产物。取决于桥接原子（X）的性质，这些产物的形成是通过进一步的氢原子易位（X = CH 2）或通过ipso引发的-攻击芳基（R = Ph），或通过直接取代杂原子（X = S）。XR = N（Me）Ph时，主要反应产物可能是不涉及相应亚氨酰基的竞争途径的结果。