N-(2-chlorophenyl)-9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-amine | 1361126-03-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-(2-chlorophenyl)-9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-amine
• 英文别名: N-(2-chlorophenyl)-9,9-dimethyl-10-phenylacridin-2-amine
• CAS: 1361126-03-5
• 化学式: C₂₇H₂₃ClN₂
• 分子量: 410.946
• InChiKey: JXQJVZQSSOZBOS-UHFFFAOYSA-N

物化性质

• 沸点：
  535.1±50.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 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-(2-chlorophenyl)-9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-amine 在 三叔丁基膦 、 palladium diacetate 、 potassium carbonate 、 caesium carbonate 、 1,3-双(2,6-二异丙基苯基)氯化咪唑鎓 作用下， 以 N,N-二甲基乙酰胺 、 甲苯 为溶剂， 反应 24.0h， 生成 6-(13,13-dimethyl-5-phenyl-5,13-dihydro-11H-indolo[2,3-b]acridin-11-yl)-3-methyl-1H-isochromen-1-one
  参考文献：
  名称：

  Highly efficient thermally activated delayed fluorescence emitters based on novel Indolo[2,3-b]acridine electron-donor

  摘要：

  Organic light emitting diodes (OLEDs) based on thermally activated delayed fluorescence (TADF) emitters have attracted much interest in recent years for their great potential in full exciton utilization. However, the lack of electron-donor candidates limits further development of TADF emitters. In this study, a novel electron-donor segment 13,13-dimethyl-5-phenyl-11,13-dihydro-5H-indolo[2,3-b]acridine (IDAC) is newly developed to construct TADF emitters. Due to the suitable steric hindrance and large planar rigid structures, IDAC derivatives could easily obtain small energy differences (Delta E(ST)s) between the lowest singlet and triplet excited states for effective TADF characteristics as well as high photoluminance quantum yields. Two novel TADF emitters, 6-(13,13-dimethyl-5-phenyl-5,13-dihydro-11H-indolo[2,3-b]acridin-11-yl)-3-methyl-1H-isochromen-1-one (IDAC-MCO) and 11-(4-(4,6-diphenyl-1,3,5-triazin-2-yl) phenyl)-13,13-dimethyl-5-phenyl-11,13-dihydro-5H-indolo[2,3-b]acridine (IDAC-Trz), are accordingly designed and synthesized, and both exhibit evident TADF characteristics with small Delta E(ST)s of 0.09 and 0.02eV and high photoluminance quantum yields of 81% and 90%, respectively. The OLEDs using IDAC-MCO and IDAC-Trz as emitters respectively achieve high external quantum efficiencies of 18.0% and 20.5% with remarkable low efficiency roll-offs. These results demonstrate the capacity of IDAC segment as an ideal electron-donor to construct efficient TADF emitters.

  DOI：

  10.1016/j.orgel.2018.03.024
• 作为产物：
  描述：

  N-苯基邻氨基苯甲酸 在 palladium diacetate N-溴代丁二酰亚胺(NBS) 、 三叔丁基膦 、 磷酸 、 caesium carbonate 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 58.17h， 生成 N-(2-chlorophenyl)-9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-amine
  参考文献：
  名称：

  [EN] NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME
  [FR] NOUVEAUX COMPOSÉS ÉLECTROLUMINESCENTS ORGANIQUES ET DISPOSITIF ÉLECTROLUMINESCENT ORGANIQUE LES UTILISANT

  摘要：

  提供了一种具有一般式I的融合五环结构的有机电致发光化合物，以及使用该化合物的有机电致发光器件。由于这些有机电致发光化合物表现出良好的发光效率和寿命，它们可以用于制造具有优越运行寿命并且由于化合物的提高功率效率而具有低功耗的OLED器件。

  公开号：

  WO2011093609A1

文献信息

• [EN] NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME<br/>[FR] NOUVEAUX COMPOSÉS ÉLECTROLUMINESCENTS ORGANIQUES ET DISPOSITIF ÉLECTROLUMINESCENT ORGANIQUE LES UTILISANT
  申请人：ROHM & HAAS ELECT MAT

  公开号：WO2011093609A1

  公开（公告）日：2011-08-04

  Provided are organic electroluminescent compounds of a fused pentacyclic structure of general formula I, and an organic electroluminescent device using said compounds. Since the organic electroluminescent compounds exhibit good luminous efficiency and lifespan, they may be used to manufacture OLED devices which have a superior operational lifetime and also have low power consumption due to the improved power efficiency of the compounds.

  提供了一种具有一般式I的融合五环结构的有机电致发光化合物，以及使用该化合物的有机电致发光器件。由于这些有机电致发光化合物表现出良好的发光效率和寿命，它们可以用于制造具有优越运行寿命并且由于化合物的提高功率效率而具有低功耗的OLED器件。
• 중수소화된 유기발광 화합물 및 이를 포함하는 유기 발광 소자
  申请人：SFC CO., LTD. 에스에프씨 주식회사(120060087061) Corp. No ▼ 135511-0105889BRN ▼134-81-54429

  公开号：KR102149450B1

  公开（公告）日：2020-09-01

  본 발명은 하기 [화학식 A로 표시되는 유기 발광 화합물 및 이를 포함하는 유기 발광 소자에 관한 것으로, 치환기Y, Ar2, L3, k, p 및 x는 발명의 상세한 설명에 정의된 바와 동일하다. [화학식 A]

  这是一个有关有机发光化合物及包含该化合物的有机发光器件的专利。其中，取代基Y，Ar2，L3，k，p和x的定义与该专利的详细描述中相同。
• [EN] NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME<br/>[FR] NOUVEAUX COMPOSÉS ÉLECTROLUMINESCENTS ORGANIQUES ET DISPOSITIF ÉLECTROLUMINESCENT ORGANIQUE L'UTILISANT
  申请人：ROHM & HAAS ELECT MAT

  公开号：WO2012039561A1

  公开（公告）日：2012-03-29

  Organic electroluminescent compounds comprising a triphenylene conjugated to a five-ring fused heterocyclic system, as depicted in formula 1 are provided. Also provided is an organic electroluminescent device comprising these compounds. The organic electroluminescent compounds disclosed herein exhibit good luminous efficiency and excellent material life. They can be used to manufacture OLED devices very superior in terms of operating life and which consume less power due to improved power efficiency.

  提供了一种包含连接到五环融合杂环系统的三苯共轭的有机电致发光化合物，如公式1所示。还提供了包含这些化合物的有机电致发光器件。本文披露的有机电致发光化合物具有良好的发光效率和优异的材料寿命。由于提高的功率效率，它们可用于制造操作寿命非常长且功耗较低的OLED器件。
• Highly efficient thermally activated delayed fluorescence emitters based on novel Indolo[2,3-b]acridine electron-donor
  作者：Jia-Xiong Chen、Wen-Wen Tao、Kai Wang、Cai-Jun Zheng、Wei Liu、Xing Li、Xue-Mei Ou、Xiao-Hong Zhang

  DOI：10.1016/j.orgel.2018.03.024

  日期：2018.6

  Organic light emitting diodes (OLEDs) based on thermally activated delayed fluorescence (TADF) emitters have attracted much interest in recent years for their great potential in full exciton utilization. However, the lack of electron-donor candidates limits further development of TADF emitters. In this study, a novel electron-donor segment 13,13-dimethyl-5-phenyl-11,13-dihydro-5H-indolo[2,3-b]acridine (IDAC) is newly developed to construct TADF emitters. Due to the suitable steric hindrance and large planar rigid structures, IDAC derivatives could easily obtain small energy differences (Delta E(ST)s) between the lowest singlet and triplet excited states for effective TADF characteristics as well as high photoluminance quantum yields. Two novel TADF emitters, 6-(13,13-dimethyl-5-phenyl-5,13-dihydro-11H-indolo[2,3-b]acridin-11-yl)-3-methyl-1H-isochromen-1-one (IDAC-MCO) and 11-(4-(4,6-diphenyl-1,3,5-triazin-2-yl) phenyl)-13,13-dimethyl-5-phenyl-11,13-dihydro-5H-indolo[2,3-b]acridine (IDAC-Trz), are accordingly designed and synthesized, and both exhibit evident TADF characteristics with small Delta E(ST)s of 0.09 and 0.02eV and high photoluminance quantum yields of 81% and 90%, respectively. The OLEDs using IDAC-MCO and IDAC-Trz as emitters respectively achieve high external quantum efficiencies of 18.0% and 20.5% with remarkable low efficiency roll-offs. These results demonstrate the capacity of IDAC segment as an ideal electron-donor to construct efficient TADF emitters.