4,4,8,8,12,12-六(4-甲基苯基)-4H,8H,12H-苯并[1,9]喹嗪并[3,4,5,6,7-defg]吖啶 | 1131007-94-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 中文名称: 4,4,8,8,12,12-六(4-甲基苯基)-4H,8H,12H-苯并[1,9]喹嗪并[3,4,5,6,7-defg]吖啶
• 中文别名: 4,4,8,8,12,12-六(4-甲基苯基)-4H,8H,12H-苯并[1,9]喹嗪并[3,4,5,6,7-DEFG]吖啶
• 英文名称: 4,4,8,8,12,12-hexa-p-tolyl-4H,8H,12H-12c-aza-dibenzo[cd,mn]pyrene
• 英文别名: 8,8,14,14,22,22-Hexakis(4-methylphenyl)-1-azahexacyclo[11.7.1.13,19.02,7.09,21.015,20]docosa-2,4,6,9(21),10,12,15,17,19-nonaene
• CAS: 1131007-94-7
• 化学式: C₆₃H₅₁N
• 分子量: 822.105
• InChiKey: DLUXZJDCDZRTSY-UHFFFAOYSA-N

物化性质

• 密度：
  1.26
• 熔点：
  Tg = 178°C (lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  16.7
• 重原子数：
  64
• 可旋转键数：
  6
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,4,8,8,12,12-六(4-甲基苯基)-4H,8H,12H-苯并[1,9]喹嗪并[3,4,5,6,7-defg]吖啶 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 生成 2,6,10-tribromo-4,4,8,8,12,12-hexakis(4-methylphenyl)-4H,8H,12H-benzo[1,9]quinolizino[3,4,5,6,7-defg]acridine
  参考文献：
  名称：

  基于联芳基亚甲基桥连的三苯胺的新型有机染料用于染料敏化太阳能电池

  摘要：

  合成了三种新型有机染料，并对它们进行了表征，以用于染料敏化太阳能电池（DSSC）。在这些染料中，二芳基亚甲基桥连的三苯胺是供体，设计了不同的受体和乙烯基噻吩以获得TBA-1，TBA-2和TBA-3。研究了它们的光物理，电化学和光伏性质，并评估了受体结构以及键合对这些性质的影响。结果表明，供体和受体之间的乙烯基噻吩键有利于提高TBA-2的光捕获能力。此外，电化学阻抗谱实验表明较大的R rec以及更长的TBA-2电子寿命。因此，它的表现优于其他染料，其最高功率转换效率为3.87％，J sc为8.25 mA·cm -2，V oc为666 mV。不幸的是，带有三个受体基团的TBA-3的效率仅为3.52％，这表明增加受体基团的设计对提高太阳能电池的效率几乎没有作用。

  DOI：

  10.1002/cjoc.201500137
• 作为产物：
  描述：

  2,2',2''-tris(di(4-methylphenyl)hydroxymethanyl)triphenylamine 在 盐酸 作用下， 以 水 、 溶剂黄146 为溶剂， 以1.48 g的产率得到4,4,8,8,12,12-六(4-甲基苯基)-4H,8H,12H-苯并[1,9]喹嗪并[3,4,5,6,7-defg]吖啶
  参考文献：
  名称：

  A Fully Diarylmethylene-Bridged Triphenylamine Derivative as Novel Host for Highly Efficient Green Phosphorescent OLEDs

  摘要：

  A fully diarylmethylene-bridged triphenylamine derivative is efficiently synthesized. It has an almost planar triphenylamine (TPA) skeleton and exhibits excellent thermal and morphological stability. Devices with the novel TPA derivative as host material and Ir(ppy)(3) as triplet emitter show a maximum current efficiency of 83.5 cd/A and a maximum power efficiency of 71.4 Im/W for green electrophosphorescence.

  DOI：

  10.1021/ol9001152

文献信息

• Novel D-π-A organic sensitizers containing diarylmethylene-bridged triphenylamine and different spacers for solar cell application
  作者：Fei Wu、Shangbi Zhao、Lawrence Tien Lin Lee、Min Wang、Tao Chen、Linna Zhu

  DOI：10.1016/j.tetlet.2015.01.156

  日期：2015.3

  planar core structure is a potential donor moiety for DSSCs. In this work, three novel D-π-A organic dyes TB-1, TB-2, and TB-3, containing diarylmethylene-bridged triphenylamine as the donor moiety, cyanoacrylic acid as the acceptor, and thiophene, benzene or furan as the π-spacers were synthesized and characterized for applications in dye-sensitized solar cells (DSSCs). Their photophysical, electrochemical

  具有几乎平面的核心结构的桥连三苯胺是DSSC的潜在供体部分。在这项工作中，三种新颖的D-π-A有机染料TB-1，TB-2和TB-3，以二芳基亚甲基桥连的三苯胺为供体部分，氰基丙烯酸为受体，并以噻吩，苯或呋喃为载体。合成了π-间隔基，并表征了其在染料敏化太阳能电池（DSSC）中的应用。研究了它们的光物理，电化学和光伏性质，比较了三苯胺供体的性能，并评估了不同的π-间隔基的作用。结果表明，与非平面的三苯胺供体相比，平面度更高的桥连TPA可以提供更好的电荷转移过程，从而具有更高的性能。另一方面，在这些化合物中 与该分子系统中的苯键相比，噻吩键和呋喃键都表现出更好的平面化和电子离域化。因此，染料TB-1和TB-3显示出更高的IPCE和J sc值。考虑到染料TB-3的较大V oc，因此它优于其他两种敏化剂，表现出3.81％的功率转换效率，在模拟AM 1.5辐射（100 mW）下的J sc为7.54 mA
• ORGANIC COMPOUND, EL DEVICE, LIGHT-EMITTING APPARATUS, ELECTRONIC APPLIANCE, LIGHTING DEVICE, AND ELECTRONIC DEVICE
  申请人：SEMICONDUCTOR ENERGY LABORATORY CO., LTD.

  公开号：US20210395245A1

  公开（公告）日：2021-12-23

  An object is to provide an organic compound with a low refractive index. Alternatively, a novel organic compound with a low refractive index and an electron-donating property is provided. Alternatively, an EL device with high emission efficiency is provided. An organic compound having an arylamine skeleton including a fluorine atom or an acridine skeleton including a fluorine atom and an EL device using the organic compound are provided. The EL device preferably includes a hole-injection layer containing the organic compound having an arylamine skeleton including a fluorine atom or an acridine skeleton including a fluorine atom and a substance showing an electron-accepting property with respect to the organic compound.

  提供一种具有低折射率的有机化合物。或者提供一种具有低折射率和电子给予性质的新型有机化合物。或者提供一种具有高发射效率的EL器件。提供一种具有含氟原子的芳胺骨架或含氟原子的吖啶骨架的有机化合物和使用该有机化合物的EL器件。EL器件最好包括含有具有含氟原子的芳胺骨架或含氟原子的吖啶骨架的有机化合物的注入层和相对于该有机化合物显示出电子受体性质的物质。
• Electronic device, light-emitting device, electronic appliance, and lighting device
  申请人：Semiconductor Energy Laboratory Co., Ltd.

  公开号：US10950805B2

  公开（公告）日：2021-03-16

  An electronic device with high outcoupling efficiency or a high light-trapping effect is provided. The electronic device includes a first layer and a second layer between a first electrode and a second electrode, the first layer is included between the first electrode and the second layer, the first layer includes a first organic compound and a first substance, the refractive index of a thin film of the first organic compound is higher than or equal to 1 and lower than or equal to 1.75, the first substance has an electron-accepting property, and the second layer has a function of emitting or absorbing light.

  提供了一种具有高出射效率或高光捕获效果的电子设备。该电子设备包括第一层和第二层，位于第一电极和第二电极之间，第一层位于第一电极和第二层之间，第一层包括第一有机化合物和第一物质，第一有机化合物的薄膜的折射率大于或等于1且小于或等于1.75，第一物质具有电子受体性质，第二层具有发射或吸收光的功能。
• Star-Shaped Oligotriarylamines with Planarized Triphenylamine Core: Solution-Processable, High-<i>T</i>_g Hole-Injecting and Hole-Transporting Materials for Organic Light-Emitting Devices
  作者：Zuoquan Jiang、Tengling Ye、Chuluo Yang、Dezhi Yang、Minrong Zhu、Cheng Zhong、Jingui Qin、Dongge Ma

  DOI：10.1021/cm1018585

  日期：2011.2.8

  optoelectronic properties can be modulated by the peripheral triarylamine groups. For example, FATPA-T with triphenylamine peripheries shows the significantly red-shifted absorption and emission, as well as the small band gap as compared to FATPA-Cz with carbazole peripheries. Double-layer Alq3-emitting OLEDs using FATPA-T or FATPA-Cz as hole-transport layer by spin-coating method were fabricated, and the

  通过铃木交叉偶联反应，合成了具有平面三苯胺核心和外围三芳基胺基团的两种新型星形低聚三芳基胺，即FATPA-T和FATPA-Cz。分子设计赋予材料以下特征：（i）极高的热稳定性和很高的玻璃化转变温度（FATPA-T为237°C，FATPA-Cz为272°C）；（ii）良好的溶液可加工性；（iii）良好的空穴迁移率，有效的空穴注入和电子阻挡功能。此外，它们的光电性质可以通过外围的三芳基胺基团来调节。例如，与具有咔唑外围的FATPA-Cz相比，具有三苯胺外围的FATPA-T显示出明显的红移吸收和发射，以及小的带隙。双层Alq 3通过旋涂法制造了使用FATPA-T或FATPA-Cz作为空穴传输层的电致发光OLED，并且与标准的基于NPB的器件相比，基于FATPA-Cz的器件通过真空蒸发NPB表现出了极大的性能提升。通过使用FATPA-Cz和NPB作为双空穴传输层来优化的三层Alq 3发光OLED的最大电流效率为6
• Electronic Device, Light-Emitting Device, Electronic Appliance, and Lighting Device
  申请人：Semiconductor Energy Laboratory Co., Ltd.

  公开号：US20200176692A1

  公开（公告）日：2020-06-04

  An electronic device with high outcoupling efficiency or a high light-trapping effect is provided. The electronic device includes a first layer and a second layer between a first electrode and a second electrode, the first layer is included between the first electrode and the second layer, the first layer includes a first organic compound and a first substance, the refractive index of a thin film of the first organic compound is higher than or equal to 1 and lower than or equal to 1.75, the first substance has an electron-accepting property, and the second layer has a function of emitting or absorbing light.