Organometallic compound and application thereof

An organometallic and compound technology, applied in indium organic compounds, platinum group organic compounds, organic chemistry, etc., can solve problems such as high sublimation temperature, poor color saturation, and unsatisfactory device performance

Active Publication Date: 2020-07-07
GUANGDONG AGLAIA OPTOELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, the invention patent document CN107973823 discloses a class of iridium compounds of quinolines, but the color saturation and device performance of such compounds, especially the luminous efficiency and device life, need to be improved; the invention patent document CN106459114 discloses a class of β-diketones Iridium compounds coordinated by ligand groups, but the sublimation temperature of this type of compound is high, and the color saturation is not good. In particular, the performance of the device is not ideal, and further improvement is needed

Method used

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  • Organometallic compound and application thereof
  • Organometallic compound and application thereof
  • Organometallic compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Synthesis of shared intermediates:

[0041]

[0042] Synthesis of compound 2:

[0043] Compound 1 (27.2g, 0.12mol, 1.2eq), 1-chloroisoquinoline (16.3g, 0.1mol, 1.0eq) and Cs 2 CO 3 (97.5g, 0.3mol, 3.0eq) and Pd(dppf)Cl 2 (3.655g, 0.05mol, 0.05eq) into a flask, add anhydrous toluene 1L, N 2 Under protection, stir and reflux at 110°C for 16 hours. Cool to room temperature, concentrate to remove the organic solvent, add 1L dichloromethane and 1L water to the residue, stir and separate the layers, and the organic phase is successively washed with H 2 O (500ml*3) and saturated aqueous sodium chloride solution (500ml*3) were washed, dried over sodium sulfate, filtered, and the filtrate was concentrated to remove the organic solvent. An off-white solid was obtained, which was purified by slurrying with EtOH to obtain compound 2 (24.33 g, yield: 78.7%). Mass spectrum: 310.12 (M+H), 1HNMR: 8.42 (d, 1H), 7.92 (dd, 1H), 7.87 (dd, 1H), 7.71 (dd, 1H), 7.50-7.57 (m, 3H), 7.3...

Embodiment 2

[0053] Synthesis of shared intermediates:

[0054]

[0055] Synthesis of compound 5:

[0056] Compound 4 (28.92g, 0.12mol, 1.2eq), 1-chloro-6 isopropylisoquinoline (20.5g, 0.1mol, 1.0eq) and Cs 2 CO 3 (97.5g, 0.3mol, 3.0eq) and Pd(dppf)Cl 2 (3.655g, 0.05mol, 0.05eq) into a flask, add anhydrous toluene 1L, N 2 Under protection, stir and reflux at 110°C for 16 hours. Cool to room temperature, concentrate to remove the organic solvent, add 1L dichloromethane and 1L water to the residue, stir and separate the layers, and the organic phase is successively washed with H 2 O (500ml*3) and saturated aqueous sodium chloride solution (500ml*3) were washed, dried over sodium sulfate, filtered, and the filtrate was concentrated to remove the organic solvent. An off-white solid was obtained, which was purified by column chromatography with ethyl acetate / petroleum ether to obtain compound 5 (28.12 g, yield: 76.8%). Mass spectrum: 367.18 (M+H), 1HNMR: 8.4 (d, 1H), 7.81 (dd, 1H), 7.7...

Embodiment 3

[0087] Synthesis of CPD 79:

[0088]

[0089] Synthesis of compound 9:

[0090] Compound 8 (29.1g, 0.12mol, 1.2eq), 1-chloroisoquinoline (16.3g, 0.1mol, 1.0eq) and Cs 2 CO 3 (97.5g, 0.3mol, 3.0eq) and Pd(dppf)Cl 2 (3.655g, 0.05mol, 0.05eq) was put into a flask, and 1L of anhydrous toluene was added, under the protection of N2, stirred and refluxed at 110°C for 16 hours. Cool to room temperature, concentrate to remove the organic solvent, add 1L dichloromethane and 1L water to the residue, stir and separate the layers, and the organic phase is successively washed with H 2 O (500ml*3) and saturated aqueous sodium chloride solution (500ml*3) were washed, dried over sodium sulfate, filtered, and the filtrate was concentrated to remove the organic solvent. An off-white solid was obtained, and the solid was separated by column chromatography to obtain compound 9 (23.41 g, yield: 72.1%). Mass spectrum: 326.1(M+H), 1HNMR: 8.51(d,1H), 7.71-7.82(m,5H), 7.50-7.60(m,3H), 7.30-7.4(...

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Abstract

The invention relates to an organometallic compound and application thereof. The organometallic compound has a structure as shown in a formula I in the specification. The compound provided by the invention has the advantages of low sublimation temperature, good optical and electrical stability, high luminous efficiency, long service life, high color saturation and the like, can be used in organiclight-emitting devices, especially as a red light-emitting phosphorescent material, and has the possibility of being applied to the AMOLED industry.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence, in particular to an organic luminescent material suitable for organic electroluminescence devices, in particular to an organometallic compound and its application in organic electroluminescence devices. Background technique [0002] At present, as a new generation of display technology, organic electroluminescent devices (OLEDs) have received more and more attention in both display and lighting technologies, and have a wide application prospect. However, compared with market application requirements, the luminous efficiency, driving voltage, service life and other performances of OLED devices need to be continuously strengthened and improved. [0003] Generally speaking, the basic structure of an OLED device is a thin film of organic functional materials with various functions mixed between metal electrodes, like a sandwich structure. Driven by current, holes and electrons are...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
CPCC07F15/0033C09K11/06C09K2211/185H10K85/342H10K50/11H10K2101/10C09K2211/1033C09K2211/1037C09K2211/1048
Inventor 鄢亮亮戴雷蔡丽菲
Owner GUANGDONG AGLAIA OPTOELECTRONICS MATERIALS
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