2,6-bis[4-(9,9-dimethyl-9,10-dihydroacridin-10-yl)phenyl]anthraquinone

• 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: 2,6-bis[4-(9,9-dimethyl-9,10-dihydroacridin-10-yl)phenyl]anthraquinone
• 英文别名: 2,6-Bis[4-(9,9-dimethylacridin-10-yl)phenyl]anthracene-9,10-dione；2,6-bis[4-(9,9-dimethylacridin-10-yl)phenyl]anthracene-9,10-dione
• 化学式: C₅₆H₄₂N₂O₂
• 分子量: 774.962
• InChiKey: XMAFAYPGYGNLSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.3
• 重原子数：
  60
• 可旋转键数：
  4
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-苯基邻氨基苯甲酸 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium phosphate 、 copper(l) iodide 、 正丁基锂 、 氯化亚砜 、 sodium t-butanolate 、 trans-1,2-cyclohexanediamine 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 115.5h， 生成 2,6-bis[4-(9,9-dimethyl-9,10-dihydroacridin-10-yl)phenyl]anthraquinone
  参考文献：
  名称：

  Anthraquinone-Based Intramolecular Charge-Transfer Compounds: Computational Molecular Design, Thermally Activated Delayed Fluorescence, and Highly Efficient Red Electroluminescence

  摘要：

  Red fluorescent molecules suffer from large, non-radiative internal conversion rates (k(IC)) governed by the energy gap law. To design efficient red thermally activated delayed fluorescence (TADF) emitters for organic light-emitting diodes (OLEDs), a large fluorescence rate (k(F)) as well as a small energy difference between the lowest singlet and triplet excited states (Delta E-ST) is necessary. Herein, we demonstrated that increasing the distance between donor (D) and acceptor (A) in intramolecular-charge-transfer molecules is a promising strategy for simultaneously achieving small Delta E-ST and large k(F). Four D-Ph-A-Ph-D-type molecules with an anthraquinone acceptor, phenyl (Ph) bridge, and various donors were designed, synthesized, and compared with corresponding D-A-D-type molecules. Yellow to red TADF was observed from all of them. The k(F) and Delta E-ST values determined from the measurements of quantum yield and lifetime of the fluorescence and TADF components are in good agreement with those predicted by corrected time-dependent density functional theory and are approximatively proportional to the square of the cosine of the theoretical twisting angles between each subunit. However, the introduction of a Ph-bridge was found to enhance k(F) without increasing Delta E-ST. Molecular simulation revealed a twisting and stretching motion of the NC bond in the D-A-type molecules, which is thought to lower Delta E-ST and k(F) but raise k(IC), that was experimentally confirmed in both solution and doped film. OLEDs containing D-Ph-A-Ph-D-type molecules with diphenylamine and bis(4-biphenyl)amine donors demonstrated maximum external quantum efficiencies of 12.5% and 9.0% with emission peaks at 624 and 637 nm, respectively.

  DOI：

  10.1021/ja510144h

文献信息

• ORGANIC ELECTROLUMINESCENT DEVICE AND MANUFACTURING METHOD THEREOF
  申请人：KUNSHAN GO-VISIONOX OPTO-ELECTRONICS CO., LTD.

  公开号：US20180175294A1

  公开（公告）日：2018-06-21

  Disclosed is an organic electroluminescent device, comprising a substrate and light emitting units formed in sequence on the substrate, characterized in that, each of the light emitting units comprises a first electrode layer ( 1 ), a light emitting layer ( 2 ) and a second electrode layer ( 3 ), the light emitting layer comprises a host material and a dye, the host material is made of materials having both electron transport capability and hole transport capability; at least one material in the host material has a CT excited triplet state energy level T 1 greater than its n-π excited triplet state energy level S 1 , and T 1 -S 1 ≤0.3 eV; or, at least one material in the host material has a CT excited triplet state energy level T 1 greater than its n-π excited triplet state energy level S 1 , and T 1 -S 1 ≥1 eV, with the difference between its n-π excited second triplet state energy level and its CT excited first singlet state energy level being in the range of −0.1 eV to 0.1 eV. The organic electroluminescent device configuration can sufficiently utilize the triplet state energy in the host material and the dye to increase the luminous efficiency and prolong the service life of the device.
• ORGANIC ELECTROLUMINESCENT DEVICE, DISPLAY PANEL AND DISPLAY DEVICE
  申请人：KUNSHAN GO-VISIONOX OPTO-ELECTRONICS CO., LTD

  公开号：US20220149281A1

  公开（公告）日：2022-05-12

  The organic electroluminescent device includes a first electrode, a second electrode and an organic layer located between the first electrode and the second electrode, the organic layer includes a light-emitting layer, the light-emitting layer includes a host material, a thermally activated delayed fluorescence sensitizer and a green fluorescent dye, the green fluorescent dye includes a structure as shown in formula I. A thermally activated sensitized fluorescence technique is used, and the green fluorescent dye of a specific structure in combination with the sensitizer and the host material is used, so as to achieve the effects of narrowing the spectrum of a device and improving the green color purity. The efficiency of the organic electroluminescent device is equivalent to that of a phosphorescent green light device, so that a display panel including the organic electroluminescent device has a large display color gamut area.
• Anthraquinone-Based Intramolecular Charge-Transfer Compounds: Computational Molecular Design, Thermally Activated Delayed Fluorescence, and Highly Efficient Red Electroluminescence
  作者：Qisheng Zhang、Hirokazu Kuwabara、William J. Potscavage、Shuping Huang、Yasuhiro Hatae、Takumi Shibata、Chihaya Adachi

  DOI：10.1021/ja510144h

  日期：2014.12.31

  Red fluorescent molecules suffer from large, non-radiative internal conversion rates (k(IC)) governed by the energy gap law. To design efficient red thermally activated delayed fluorescence (TADF) emitters for organic light-emitting diodes (OLEDs), a large fluorescence rate (k(F)) as well as a small energy difference between the lowest singlet and triplet excited states (Delta E-ST) is necessary. Herein, we demonstrated that increasing the distance between donor (D) and acceptor (A) in intramolecular-charge-transfer molecules is a promising strategy for simultaneously achieving small Delta E-ST and large k(F). Four D-Ph-A-Ph-D-type molecules with an anthraquinone acceptor, phenyl (Ph) bridge, and various donors were designed, synthesized, and compared with corresponding D-A-D-type molecules. Yellow to red TADF was observed from all of them. The k(F) and Delta E-ST values determined from the measurements of quantum yield and lifetime of the fluorescence and TADF components are in good agreement with those predicted by corrected time-dependent density functional theory and are approximatively proportional to the square of the cosine of the theoretical twisting angles between each subunit. However, the introduction of a Ph-bridge was found to enhance k(F) without increasing Delta E-ST. Molecular simulation revealed a twisting and stretching motion of the NC bond in the D-A-type molecules, which is thought to lower Delta E-ST and k(F) but raise k(IC), that was experimentally confirmed in both solution and doped film. OLEDs containing D-Ph-A-Ph-D-type molecules with diphenylamine and bis(4-biphenyl)amine donors demonstrated maximum external quantum efficiencies of 12.5% and 9.0% with emission peaks at 624 and 637 nm, respectively.