Blue light organic electrophosphorescent material iridium metal complex, preparation method thereof, and organic electroluminescent device

A technology of iridium metal complexes and phosphorescent materials, which is applied in the field of organic electroluminescent materials, can solve problems such as poor blue light color purity, and achieve the effects of facilitating evaporation, reducing evaporation temperature, and reducing self-quenching

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

Bis(4,6-difluorophenylpyridine-N,C2) pyridine iridium iridium (FIrpic) is currently the most reported blue-light organic electrophosphorescent material with the best comprehensive performance. Various optimizations have greatly improved the performance of the device, but the biggest weakness of FIrpic is that the blue light emitted by FIrpic is sky blue, and the color purity of the blue light is not good. ), which has a large gap with the standard Blu-ray CIE (0.137,0.084)

Method used

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  • Blue light organic electrophosphorescent material iridium metal complex, preparation method thereof, and organic electroluminescent device
  • Blue light organic electrophosphorescent material iridium metal complex, preparation method thereof, and organic electroluminescent device
  • Blue light organic electrophosphorescent material iridium metal complex, preparation method thereof, and organic electroluminescent device

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Experimental program
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preparation example Construction

[0041] see figure 1 , the preparation method of the above-mentioned blue light organic electrophosphorescent material iridium metal complex, comprising the following steps:

[0042] S1, under the protection of inert gas, the structural formula is The compound A and the structural formula are Compound B is dissolved in an organic solvent containing a catalyst and a base to obtain a reaction solution, which is subjected to a Suzuki coupling reaction at a temperature of 80 to 90°C for 10 to 15 hours. After the reaction is stopped, the reaction solution is separated and purified to obtain the structural formula for ring metal ligand; wherein, the molar ratio of compound A to compound B is 1:1~1:1.5; wherein, R is C 1 ~C 20 The alkoxy group; the reaction formula is:

[0043]

[0044] S2. Under the protection of an inert gas, the cyclometal ligand and iridium trichloride trihydrate are dissolved in a mixed solvent formed by 2-ethoxyethanol and water at a molar ratio of 2:...

Embodiment 1

[0070] Example 1: Complex bis(2-(2',6'-difluoropyridin-3'-yl)-5-methoxypyrimidine-N,C 4 ')(tetrakis(1-pyrazole) boron) iridium synthesis

[0071] (1) Synthesis of 2-(2',6'-difluoropyridin-3'-yl)-5-methoxypyrimidine

[0072]

[0073] Under nitrogen protection, 1.89g (10mmol) 2-bromo-5-methoxypyrimidine (A1), 1.91g (12mmol) 2,6-difluoropyridine-3-boronic acid (B) and 0.58g (0.5mmol) Tetrakis(triphenylphosphine)palladium was dissolved in 35mL of toluene, and then 15mL of an aqueous solution containing 2.76g (20mmol) of potassium carbonate was added dropwise to the reaction system to form a reaction solution. The reaction solution was heated and stirred for 10 h at a temperature of 90°C. After the reaction solution was cooled to room temperature, it was extracted with dichloromethane, separated, washed with water until neutral, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was distilled off the solvent under reduced pressure to obtain the crude p...

Embodiment 2

[0092] Example 2: Complex bis(2-(2',6'-difluoropyridin-3'-yl)-4-hexyloxypyrimidine-N,C 4 ')(tetrakis(1-pyrazole) boron) iridium synthesis

[0093] (1) Synthesis of 2-(2',6'-difluoropyridin-3'-yl)-4-hexyloxypyrimidine

[0094]

[0095] Under nitrogen protection, 1.30g (5mmol) 2-bromo-4-hexyloxypyrimidine (compound A2), 0.79g (5mmol) compound B and 0.14g (0.2mmol) dichlorobis (triphenylphosphine) palladium Dissolve in 35mL of DMF, and then dropwise add 15mL of an aqueous solution containing 2.07g (15mmol) of potassium carbonate to the reaction system to form a reaction solution. The reaction solution was heated to 80° C. and stirred for 12 h. After the reaction solution was cooled to room temperature, it was extracted with dichloromethane, separated, washed with water until neutral, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was distilled off the solvent under reduced pressure to obtain the crude product. Silica gel column chromatography wa...

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Abstract

The invention discloses a blue light organic electrophosphorescent material iridium metal complex, a preparation method thereof, and an organic electroluminescent device. A structural general formula of the material is shown in the description. In the structural general formula, R represents alkoxy of C1-C20. The blue light organic electrophosphorescent material iridium metal complex is synthesized by using 2-(2',6'-difluoropyridine-3'-yl)pyrimidine as cyclometalated ligands and tetra(1-pyrazolyl)borate as auxiliary ligands. Regulation of luminescent colors of the material is realized through chemical modification by introducing alkoxy chains on pyrimidine rings of the cyclometalated ligands, and thus phosphorescence emission with wavelengths nearer to that of blue light can be obtained.

Description

technical field [0001] The invention relates to an organic electroluminescent material, in particular to a blue-light organic electroluminescent material iridium metal complex, a preparation method thereof and an organic electroluminescent 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 ne...

Claims

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Application Information

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