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Phosphorescence iridium complexes, preparing method thereof and organic electroluminescent device

An iridium metal complex, organic technology, used in luminescent materials, electro-solid devices, organic chemistry, etc., can solve the problems of low efficiency and difficult to obtain satisfactory luminescent performance.

Inactive Publication Date: 2014-12-03
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the efficiency of the current red phosphorescence luminescent materials is relatively low, and it is difficult to obtain satisfactory luminescent performance when they are applied to electroluminescent devices.

Method used

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  • Phosphorescence iridium complexes, preparing method thereof and organic electroluminescent device
  • Phosphorescence iridium complexes, preparing method thereof and organic electroluminescent device
  • Phosphorescence iridium complexes, preparing method thereof and organic electroluminescent device

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preparation example Construction

[0034] see figure 1 , the preparation method of the red phosphorescence iridium metal complex of an embodiment, comprises the steps:

[0035] Step S110: In an inert gas atmosphere, dissolve Ar-Br and acenaphthyl-5-boronic acid with a molar ratio of 4:4.5 to 4:5 in the first solvent, add a catalyst and an aqueous carbonate solution, and perform Suzuki coupling React for 8 to 12 hours, obtain compound A after separation and purification, and the structural formula of compound A is , where —Ar is

[0036] The inert gas is argon, helium or neon.

[0037] The Suzuki coupling reaction was carried out under reflux.

[0038] The first solvent is toluene or tetrahydrofuran (THF). The amount of the first solvent is suitable to fully dissolve Ar-Br and acenaphthylene-5-boronic acid. Preferably, the solid-to-liquid ratio of acenaphthyl-5-boronic acid to the first solvent is 4.8 mmol: 30 mL to 5 mmol: 20 mL.

[0039] The catalyst is an organic palladium catalyst, specifically tetr...

Embodiment 1

[0072] Red Phosphorescent Tris[1-(Acenaphthyl-5-yl)phthalazine-N,C 2 '] Synthesis of iridium complexes

[0073] Red Phosphorescent Tris[1-(Acenaphthyl-5-yl)phthalazine-N,C 2 '] The structural formula of the iridium complex is as follows:

[0074]

[0075] (1) Synthesis of 1-(acenaphthyl-5-yl)phthalazine

[0076]

[0077] Under argon protection, 0.84g (4mmol) 1-bromophthalazine, 0.95g (4.8mmol) acenaphthene-5-boronic acid and 0.23g (0.20mmol) tetrakistriphenylphosphine palladium were dissolved in 30mL of toluene, and then poured into the reaction system 10 mL of an aqueous solution containing 0.85 g (8 mmol) of sodium carbonate was added dropwise. Heated and stirred under reflux for 10h. After the reaction was complete, it was naturally cooled to room temperature, and extracted three times with 15 mL of water and 15 mL of ethyl acetate successively. The organic phase was dried over anhydrous magnesium sulfate and filtered. The solvent was removed from the filtrate b...

Embodiment 2

[0105] Red phosphorescent tris[3-(acenaphthyl-5-yl)cinnoline-N,C 2 '] Synthesis of iridium complexes

[0106] Red phosphorescent tris[3-(acenaphthyl-5-yl)cinnoline-N,C 2 '] The structural formula of the iridium complex is as follows:

[0107]

[0108] (1) Synthesis of 3-(acenaphthyl-5-yl)cinnoline

[0109]

[0110] Under the protection of argon, 0.84g (4mmol) 3-bromocinnoline, 0.99g (5mmol) acenaphthene-5-boronic acid and 0.28g (0.24mmol) tetrakistriphenylphosphine palladium were dissolved in 25mL THF, and then poured into the reaction system 10 mL of an aqueous solution containing 1.38 g (10 mmol) of potassium carbonate was added dropwise. Heated and stirred under reflux for 12h. After the reaction was complete, it was naturally cooled to room temperature, and extracted three times with 10 mL of water and 10 mL of ethyl acetate, respectively. The organic phase was dried over anhydrous magnesium sulfate and filtered. The solvent was removed from the filtrate by rot...

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Abstract

The invention relates to phosphorescence iridium complexes, a preparing method thereof and an organic electroluminescent device. The red phosphorescence iridium complexes are characterized in that: the structure formula of the complexes is shown in the specification, wherein -Ar is shown in the specification. The red phosphorescence iridium complexes can improve electroluminescent properties of the organic electroluminescent device.

Description

technical field [0001] The invention relates to the technical field of electroluminescence materials, in particular to a phosphorescence material iridium metal complex, a preparation method thereof and an organic electroluminescence device. Background technique [0002] Organic electroluminescence refers to a luminescence phenomenon in which organic materials directly convert electrical energy into light energy under the action of an electric field. In the early days, the research on organic electroluminescence was stagnant because of the high driving voltage and low luminous efficiency of organic electroluminescent devices. Until 1987, people such as Tang of American Kodak Company invented 8-hydroxyquinoline aluminum (Alq 3 ) is a light-emitting material, and a uniform and dense high-quality thin film is made with aromatic diamines, and an organic electroluminescent device with low operating voltage, high brightness, and high efficiency is prepared, which opens a new prelu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
Inventor 周明杰王平张娟娟冯小明
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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