3-(diphenylphosphonyl)-9-phenyl-9H-carbazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(diphenylphosphonyl)-9-phenyl-9H-carbazole
• 英文别名: 3-Diphenylphosphoryl-9-phenylcarbazole；3-diphenylphosphoryl-9-phenylcarbazole
• 化学式: C₃₀H₂₂NOP
• 分子量: 443.485
• InChiKey: APUXUWZBISIRRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-溴-N-苯基咔唑 在 正丁基锂 、 双氧水 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 3-(diphenylphosphonyl)-9-phenyl-9H-carbazole
  参考文献：
  名称：

  JP5663566

  摘要：

  公开号：

文献信息

• CARBAZOLE-BASED PHOSPHINE OXIDE COMPOUND, AND ORGANIC ELECTROLUMINESCENT DEVICE INCLUDING THE SAME
  申请人：Lee Jun-Yeob

  公开号：US20120068168A1

  公开（公告）日：2012-03-22

  The present invention relates to a carbazole-based phosphine oxide compound, and an organic electroluminescent device including the same. According to the present invention, provided are a compound for an organic electroluminescent device which can improve the thermal stability and efficiency characteristics which are unstable and low, respectively, corresponding to problems of known compounds for organic electroluminescent devices, and particularly, can implement excellent efficiency characteristics in a pure blue phosphorescent device, by using the carbazole-based phosphine oxide compound of the compound for the organic electroluminescent device, and the organic electroluminescent device. According to one aspect of the present invention, the carbazole-based phosphine oxide compound of the compound for the organic electroluminescent device is provided, and the organic electroluminescent device containing the same which can implement thermal stability and high efficiency characteristics is also provided.

  本发明涉及一种基于咔唑的膦氧化物化合物和包括该化合物的有机电致发光器件。根据本发明，提供了一种用于有机电致发光器件的化合物，可以改善已知有机电致发光器件化合物存在的热稳定性和效率特性不稳定和低下的问题，特别是可以通过使用该有机电致发光器件化合物中的基于咔唑的膦氧化物化合物，在纯蓝色磷光器件中实现优异的效率特性。根据本发明的一个方面，提供了用于有机电致发光器件的基于咔唑的膦氧化物化合物，并提供了包括该化合物的有机电致发光器件，该器件可以实现热稳定性和高效率特性。
• Synthesis and Anticancer Activity of Phosphinoylated and Phosphonoylated <i>N</i>‐Heterocycles Obtained by the Microwave‐Assisted Palladium Acetate‐Catalyzed Hirao Reaction
  作者：Bianka Huszár、Renáta Szolga、Szilvia Bősze、Rita Oláhné Szabó、András Simon、Konstantin Karaghiosoff、Mátyás Czugler、László Drahos、György Keglevich

  DOI：10.1002/chem.202302465

  日期：2023.12.6

  A literature survey showed that different derivatives with the 9‐phenyl‐9H‐carbazole or the dihydroindoline scaffold may be of biological activity including cytotoxic effect. Driven by this experience, P‐functionalized derivatives of these N‐heterocycles were synthesized. Three N‐heterocycles, 9‐(4‐bromophenyl)‐9H‐carbazole, 3‐bromo‐9‐phenyl‐9H‐carbazole and 1‐(5‐bromoindolin‐1‐yl)ethan‐1‐one, were coupled with dialkyl phosphites and diarylphosphine oxides using Pd(OAc)₂ (10 %) as the catalyst precursor and triethylamine as the base in ethanol under microwave irradiation. The excess of the Y₂P(O)H reagent (Y=alkoxy, aryl) (30 %) served as the P‐ligand in its trivalent tautomeric form (Y₂POH), hence there was no need for the usual P‐ligands meaning cost and environmental burden. Hence, the presented method is a “green” approach that proved to be more efficient than the preparation by the traditional method. The products, dialkyl phosphonates and tertiary phosphine oxides obtained in 58–84 % yields were characterized, one of them also by single crystal X‐ray analysis, and were subjected to in vitro biological activity evaluation. A (carbazol)yl‐phenylphosphonate, an N‐phenyl‐(carbazol)yl‐phosphonate, a (carbazol)yl‐phenylphosphine oxide and an N‐phenyl‐(carbazol)ylphosphine oxide revealed a significant cytotoxic activity on A549 human non‐small‐cell lung carcinoma and MonoMac‐6 acute monocytic leukemia cancer cells. The cytotoxic effect was significant as compared to that of the reference compounds.

  摘要 文献调查显示，具有 9-苯基-9H-咔唑或二氢吲哚啉支架的不同衍生物可能具有生物活性，包括细胞毒性作用。在这一经验的推动下，我们合成了这些 N-杂环的 P-官能化衍生物。在微波辐照下，以 Pd(OAc)2 (10 %) 为催化剂前体，以三乙胺为碱，在乙醇中将 9-(4-溴苯基)-9H-咔唑、3-溴-9-苯基-9H-咔唑和 1-(5-溴吲哚啉-1-基)乙-1-酮这三种 N-杂环与二烷基亚磷酸盐和二芳基膦氧化物偶联。过量的 Y2P(O)H 试剂（Y=烷氧基、芳基）（30%）以其三价同分异构形式（Y2POH）作为 P 配体，因此无需使用通常的 P 配体，这意味着成本和环境负担。因此，所介绍的方法是一种 "绿色 "方法，事实证明比传统方法更有效。以 58-84% 的收率获得的产品、二烷基膦酸盐和叔膦氧化物的特征，其中一种还通过了单晶 X 射线分析，并进行了体外生物活性评估。一种（咔唑）酰基苯基膦酸盐、一种 N-苯基-（咔唑）酰基膦酸盐、一种（咔唑）酰基苯基氧化膦和一种 N-苯基-（咔唑）酰基氧化膦对 A549 人类非小细胞肺癌和 MonoMac-6 急性单核细胞白血病癌细胞具有显著的细胞毒活性。与参考化合物相比，其细胞毒性效果显著。
• LIGHT-EMITTING DEVICE AND AN ELECTRONIC DEVICE INCLUDING THE SAME
  申请人：Samsung Display Co., Ltd.

  公开号：US20220190296A1

  公开（公告）日：2022-06-16

  A light-emitting device includes: a first electrode; a second electrode facing the first electrode; an interlayer between the first electrode and the second electrode and including an emission layer; and a first capping layer and a second capping layer outside the second electrode, wherein the first capping layer includes at least one compound selected from compounds represented by Formulae 1-1 to 1-3, as defined herein, and the second capping layer includes at least one compound selected from compounds represented by Formulae 2-1 to 2-6, as defined herein.
• US9278986B2
  申请人：——

  公开号：US9278986B2

  公开（公告）日：2016-03-08