1,2-bis(4-bromophenyl)-1H-benzo[d]imidazole | 1169709-28-7

• 物质功能分类: 有机原料 - 杂环化合物
• 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: 1,2-bis(4-bromophenyl)-1H-benzo[d]imidazole
• 英文别名: 1,2-Bis(4-bromophenyl)-1H-benzimidazole；1,2-bis(4-bromophenyl)benzimidazole
• CAS: 1169709-28-7
• 化学式: C₁₉H₁₂Br₂N₂
• 分子量: 428.126
• InChiKey: QPIMDVGUWUFTAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  23
• 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：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2-bis(4-bromophenyl)-1H-benzo[d]imidazole 在 双氧水 、 sodium acetate 、 palladium diacetate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 1,2-bis(4-(diphenylphosphoryl)phenyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  电子传输材料的双重封装可简化高效蓝色热激活延迟荧光器件

  摘要：

  简化蓝色热激活延迟荧光（TADF）二极管时，电荷通量平衡和界面优化是两个核心问题，这反映了对载流子传输材料（CTM）的更严格的要求，这是电荷传输和淬灭抑制之间矛盾的体现。对分子间相互作用的要求相反。在此，以苯基苯并咪唑（PBI）为核心，被两个二苯基氧化膦（DPPO）取代，形成了六种双包封的电荷-激子分离（CES）型电子传输材料（ETM），其总名称为xy PBIDPO。通过调节DPPO基团的取代位置，将其共振和空间效应两个功能进行了整合和优化，以增强带电部分的封装，而无需降低电活性。结果，在xy PBIDPO中，mm PBIDPO凭借其两倍的台面取代结构和大致对称的构型成功实现了良好的电性能和界面相互作用抑制之间的平衡，从而实现了2.8 eV的良好电子亲和力，高电子迁移率。 10 –6 cm 2 V –1 s –1的水平和有效的PBI核心封装。因此，mm PBIDPO被用来极大简化蓝色TAD

  DOI：

  10.1021/acs.chemmater.6b03518
• 作为产物：
  描述：

  4-溴-n-(2-硝基苯基)苯胺 在 溶剂黄146 、 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 36.0h， 生成 1,2-bis(4-bromophenyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  KR2015/14776

  摘要：

  公开号：

文献信息

• NITROGEN-CONTAINING HETEROCYCLIC DERIVATIVE AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME
  申请人：Idemitsu Kosan Co., Ltd.

  公开号：EP2236501A1

  公开（公告）日：2010-10-06

  A novel nitrogen-containing heterocyclic derivative having a specific structure. An organic electroluminescence device comprises an organic thin-film layer which is disposed between a cathode and an anode and comprises one or more layers having a light emitting layer. At least one layer of the organic thin-film layer comprises the nitrogen-containing heterocyclic derivative. The organic electroluminescence device exhibits a high luminance and a high luminous efficiency even at a low driving voltage.

  一种具有特定结构的新型含氮杂环衍生物。一种有机电致发光器件包括一个有机薄膜层，该有机薄膜层位于阴极和阳极之间，并包括一个或多个具有发光层的层。有机薄膜层的至少一层包括含氮杂环衍生物。该有机电致发光器件在低驱动电压下表现出高亮度和高发光效率。
• Manipulating charge carrier transporting of disubstituted phenylbenzoimidazole-based host materials for efficient full-color PhOLEDs
  作者：Hui-Ting Mao、Wei-Lin Song、Chun-Xiu Zang、Guang-Fu Li、Guo-Gang Shan、Hai-Zhu Sun、Wen-Fa Xie、Zhong-Min Su

  DOI：10.1016/j.orgel.2019.105513

  日期：2020.2

  successfully applied as universal hosts in the fabrication of full-color PhOLEDs. The effect of substituted groups on the photophysical, theoretical calculations, and electrochemical characters for host materials is systematically investigated. We adopt the same device architecture to fabricate the blue, green, yellow, and red PhOLEDs with the combination of the three hosts. As a result, DPOPBI and POCzPBI

  许多努力集中在探索能够在磷光有机发光器件（PhOLED）中起作用的高效主体材料上。然而，迄今为止报道的通常适合于全色设备的高级主机很少见，并且由此产生的设备性能远不能令人满意。一类宿主化合物DCzPBI，POCzPBI和DPOPBI分别合成了咔唑和二苯基氧化膦基团作为供电子基团和受电子基团，并成功地将其作为通用主体用于制造全色PhOLED。系统地研究了取代基对基质材料的光物理，理论计算和电化学特性的影响。我们采用相同的设备架构，结合这三个主机来制造蓝色，绿色，黄色和红色PhOLED。结果，具有良好的电荷载流子传输特性的DPOPBI和POCzPBI为设备提供了令人印象深刻的效率。最佳电流效率（CE）为23.2、48.4、45.7、21.5 cd A -1分别用于蓝色，绿色，黄色和红色设备。即使在1000 cd m -2的亮度下，绿色器件的效率下降仅为2％，黄色器件的效率下降仅为0.2％，这表
• π-stacking and C—<i>X</i>...<i>D</i>(<i>X</i>= H, NO₂;<i>D</i>= O, π) interactions in the crystal network of both C—H...N and π-stacked dimers of 1,2-bis(4-bromophenyl)-1<i>H</i>-benzimidazole and 2-(4-bromophenyl)-1-(4-nitrophenyl)-1<i>H</i>-benzimidazole
  作者：Jazmin E. González-Padilla、Martha C. Rosales-Hernández、Itzia I. Padilla-Martínez、Efren V. García-Báez、Susana Rojas-Lima、Veronica Salazar-Pereda

  DOI：10.1107/s2053229613033329

  日期：2014.1.1

  Molecules of 1,2-bis(4-bromophenyl)-1H-benzimidazole, C₁₉H₁₂Br₂N₂, (I), and 2-(4-bromophenyl)-1-(4-nitrophenyl)-1H-benzimidazole, C₁₉H₁₂BrN₃O₂, (II), are arranged in dimeric units through C—H...N and parallel-displaced π-stacking interactions favoured by the appropriate disposition of N- and C-bonded phenyl rings with respect to the mean benzimidazole plane. The molecular packing of the dimers of (I) and (II) arises by the concurrence of a diverse set of weak intermolecular C—X...D(X= H, NO₂;D= O, π) interactions.

  1,2-双(4-溴苯基)-1H-苯并咪唑 C19H12Br2N2 (I) 和 2-(4-溴苯基)-1-(4-硝基苯基)-1H-苯并咪唑 C19H12BrN3O2 (II) 分子通过 C-H.N 键和 C 键苯基环相对于苯并咪唑平均平面的适当位置有利于 N 键和 C 键的平行错位 π 堆积相互作用。(I)和(II)二聚体的分子堆积是由多种微弱的分子间 C-X...D（X= H，NO2；D= O，π）相互作用共同作用产生的。
• Efficient deep-blue emitters based on triphenylamine-linked benzimidazole derivatives for nondoped fluorescent organic light-emitting diodes
  作者：Seongjin Jeong、Myoung-Ki Kim、Sung Hyun Kim、Jong-In Hong

  DOI：10.1016/j.orgel.2013.06.022

  日期：2013.10

  Two triphenylamine-substituted benzimidazole derivatives were synthesized for use as efficient deep-blue emitters in nondoped fluorescent organic light-emitting diodes (FLOLEDs). The molecular design of 4',4 ''-(1H-benzo[d]imidazole-1,2-diyl)bis(N,N-diphenylbiphenyl-4-amine) (T2B) to limit the molecular packing density enabled T2B-based devices to suppress the exciton quenching by a bulky three-dimensional structure. Nondoped FLOLEDs fabricated using T2B as a blue emitter exhibited an external quantum efficiency of 4.67% with color coordinates of (0.15, 0.08). (C) 2013 Elsevier B.V. All rights reserved.
• Organometallic Ir(III) Phosphors Decorated by Carbazole/Diphenylphosphoryl Units for Efficient Solution-Processable OLEDs with Low Efficiency Roll-Offs
  作者：Wei-Lin Song、Hui-Ting Mao、Guo-Gang Shan、Ying Gao、Gang Cheng、Zhong-Min Su

  DOI：10.1021/acs.inorgchem.9b01601

  日期：2019.10.21

  Recently, solution-processable PhOLEDs have been attracting great interest for their low cost and high productivity relative to the vacuum-deposited devices. Similar to vacuum-deposited OLEDs, however, they usually suffer from serious efficiency roll-offs, especially in high brightness. Finding a feasible way and/or designing novel materials to increase efficiencies and reduce roll-offs simultaneously are highly desired. Herein, a new family of solution-processable cyclometalated iridium(III) phosphors with carbazole (Cz) and/or diphenylphosphoryl (Ph2PO) units functionalized main ligands has been designed. Owing to Cz and Ph2PO moieties possessing bulky steric effects, they can suppress the intermolecular strong packing and then decrease TTA effects and emission quenching. Meanwhile, the resulting OLEDs based on the designed phosphors exhibit considerable efficiencies and relatively small efficiency roll-offs. The device based on 4 containing both Cz and Ph2PO units realized a maximum current efficiency of 21.3 cd A(-1), accompanied by a small roll-off. By optimization of the configuration of OLEDs, the device performance can be further enhanced, demonstrating their potential for high-performance solution-processable PhOLEDs.