Iridium-containing metal complex and organic light-emitting device thereof

A technology of organic light-emitting devices and metal complexes, applied in the field of iridium-containing metal complexes and organic light-emitting devices, can solve the problems of low driving voltage, short life, low luminous efficiency and the like

Inactive Publication Date: 2018-11-27
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, organic light-emitting devices have been developed towards practicality and commercialization, but there are still deficiencies. Phosphorescent materials generally have problems of poor thermal stability, low luminous efficiency, and short life. The fundamental factors that determine the performance of organic electroluminescent devices are: Therefore, it is urgent to design and develop an organometallic complex with higher luminous efficiency and low driving voltage

Method used

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  • Iridium-containing metal complex and organic light-emitting device thereof
  • Iridium-containing metal complex and organic light-emitting device thereof
  • Iridium-containing metal complex and organic light-emitting device thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0059] Preparation of Intermediate A

[0060] Compound A and SOCl 2 Mix in a three-necked flask, reflux, cool, and vacuum distill to remove SOCl 2 , adding diethylamine for treatment, stirring, washing, and drying to obtain compound B. Compound B was refluxed with dioxane and potassium carbonate aqueous solution, stirred vigorously, cooled, diluted, washed and dried to obtain compound D. Compound D was mixed with THF, stirred, added LDA, reacted overnight, extracted with dichloromethane, and separated by column chromatography to obtain Compound E. Compound E was reacted with DMDO to obtain compound F. Compound F was mixed with anhydrous hydrazine and anhydrous methanol, stirred and washed to obtain solid powder G. Compound G and norbornadiene were mixed and refluxed, heated, cooled, diluted, washed, dried, and chromatographically separated to obtain compound H. Compound H was dissolved in 3:1 2-ethoxyethanol / water (40ml), nitrogen was bubbled for 15min, followed by the ad...

Embodiment 1

[0066] Embodiment 1: the preparation of compound 1

[0067]

[0068] Preparation of Intermediate A

[0069] Compound 1-1 27.4g and 100ml of SOCl 2 Added to a three-necked flask, the mixture was refluxed for 2 hours, and the red-orange solution was cooled to ambient temperature. Remove excess SOCl by vacuum distillation 2 , and then washed 3 times with anhydrous toluene, the resulting solid acid chloride was suspended in 300ml of anhydrous dichloromethane, cooled in an ice-water bath, and 40ml of diethylamine was added for treatment, then the solution was stirred overnight at room temperature, and bicarbonate was added Washed with aqueous sodium and ammonium chloride, the organic phase was dried over sodium sulfate and evaporated in vacuo to give 29.2 g of yellow solid 1-2, 84% yield.

[0070] Under the protection of nitrogen, 8.5g of compound 1-2 and 5.3g of 2,6-dimethylphenylboronic acid, 100ml of dioxane and 50ml of 2M potassium carbonate aqueous solution were put into...

Embodiment 2

[0079] Embodiment 2: the preparation of compound 15

[0080] 1-3 in Example 1 was replaced by equimolar 15-3, and the other steps were the same as in Example 1 to obtain the target compound 15.

[0081]

[0082] Mass Spectrum m / z: 993.03 (calculated: 993.04). Theoretical element content (%)C 45 h 34 f 6 IrN 8 : C, 54.43; H, 3.45; F, 11.48; Ir, 19.36; N, 11.28 The measured element content (%): C, 54.42; The above results confirmed that the obtained product was the target product.

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Abstract

The invention provides an iridium-containing metal complex and an organic light-emitting device thereof. The iridium-containing metal complex has a structure as shown in formula (I), and the structurecomprises a first ligand and an auxiliary ligand, wherein an electron-rich dinitrogen coordination structure in the auxiliary ligand structure is favorable for stabilizing central trivalent metal cations. Meanwhile, electronic cloud distribution on metal iridium is influenced, the photoelectric property of the whole complex molecule is greatly influenced, the four-membered ring formed by the ligand of the dinitrogen coordination structure and metals has high rigidity, unnecessary vibration energy losses are reduced, and an efficient luminescence property is realized. By regulating substituentgroups, the complex has excellent heat stability and chemical properties. The iridium-containing metal complex is prepared into devices, and particularly serves as a doped material. The device has the advantages of low driving voltage and high luminous efficiency, and is better than the existing common OLED (Organic Light-Emitting Device).

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to an iridium-containing metal complex and an organic light-emitting device thereof. Background technique [0002] In 1987, Deng Qingyun and others from Kodak Corporation of the United States first evaporated organic compounds into amorphous organic thin films by vacuum evaporation, and selected different organic materials as hole and electron transport layers to prepare double-layer OLED devices. When the voltage of the device is about 10V, the brightness of the device reaches 1000cd m -2 , the maximum external quantum efficiency EQE (External Quantum Efficiency) is about 1%, showing a very good electroluminescent performance, which indicates that the organic electroluminescent device (OLED) has the possibility of practical application. Since then, Major companies and scientific research institutions have invested a lot of manpower and resources in the rese...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
CPCC09K11/06C07F15/0033C09K2211/1029C09K2211/1044C09K2211/185H10K85/342
Inventor 蔡辉张弘
Owner CHANGCHUN HYPERIONS TECH CO LTD
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