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Blue 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 reducing self-quenching, high luminous efficiency, and good stability

Inactive Publication Date: 2014-10-29
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 organic electrophosphorescent material iridium metal complex, preparation method thereof and organic electroluminescent device
  • Blue organic electrophosphorescent material iridium metal complex, preparation method thereof and organic electroluminescent device
  • Blue 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

[0036] The preparation method of the above-mentioned blue light organic electrophosphorescent material iridium metal complex comprises the following steps:

[0037] (1) Under the protection of inert gas (at least one of nitrogen and argon, the same below), the structural formula is The compound A and the structural formula are The compound B is dissolved in the first organic solvent containing catalyst and base, and then reflux Suzuki coupling reaction at 80-100°C for 4-5h. After the reaction is stopped, the reaction solution is separated and purified to obtain the structural formula: The ring metal ligand; Wherein, the molar ratio of compound A and compound B is 1:1~1:2; Reaction formula is as follows:

[0038]

[0039] In the formula, R is a hydrogen atom, C 1 ~C 4 straight or branched chain alkyl or C 1 ~C 4 straight-chain or branched-chain alkoxy groups.

[0040](2) Under the protection of an inert gas, dissolve the cyclometal ligand and iridium acetylacetonate...

Embodiment 1

[0060] Example 1: Complex tris(3-(2',6'-difluoropyridin-3'-yl)pyridazine-N,C 2 ’) Synthesis of iridium

[0061] (1) Synthesis of 3-(2',6'-difluoropyridin-3'-yl)pyridazine

[0062]

[0063] Under nitrogen protection, 3.18g (20mmol) 3-bromopyridazine (A1), 3.81g (24mmol) 2,6-difluoropyridine-3-boronic acid (B), 80mL toluene, 20mL water, 3.22 g (10mmol) tetrabutylammonium bromide, 5.53g (40mmol) anhydrous potassium carbonate, 0.23g (0.2mmol) tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 ), and then stirred and refluxed at 80°C for 5h. 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 was carried out with dichloromethane as the eluent. After drying, 2.51 g of solid was obtained, with a...

Embodiment 2

[0081] Example 2: Complex tris(3-(2',6'-difluoropyridin-3'-yl)-6-methylpyridazine-N,C 2 ’) Synthesis of iridium

[0082] (1) Synthesis of 3-(2',6'-difluoropyridin-3'-yl)-6-methylpyridazine

[0083]

[0084] Under nitrogen protection, 3.46g (20mmol) 3-bromo-6-methylpyridazine (A2), 3.18g (20mmol) B, 80mL DMF, 20mL water, 3.22g (10mmol) tetrabutyl bromide were added to the reactor Ammonium chloride, 10.6g (100mmol) anhydrous sodium carbonate, 0.23g (0.2mmol) tetrakis(triphenylphosphine)palladium, stirred and refluxed at 100°C for 4h. 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 was carried out with dichloromethane as the eluent. After drying, 2.49 g of solid was obtained, with a yield of 60...

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Abstract

The invention discloses a blue 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 specification, wherein R is a hydrogen atom, C1-C4 linear or branched alkyl or C1-C4 linear or branched alkoxy. The blue organic electrophosphorescent material iridium metal complex provided by the invention has the beneficial effects that the blue organic electrophosphorescent material iridium metal complex takes 3-(2',6'-difluoropyridine-3'-yl)pyridazine or a derivative thereof as a cyclic metal ligand; the satisfactory energy transfer efficiency and blue light emitting wavelength can be obtained and certain steric hindrance effects can be generated by introducing alkyl and alkoxy, thus reducing direction actions among metal atoms and reducing the self-quenching phenomenon of triplet excitons; meanwhile, substitution of two F-based strong electron-withdrawing groups on a stiffening pyridine ring can not only effectively perform blue shift on the light emitting wavelength but also improve the light emitting properties, thereby being beneficial for evaporation and improving the film-forming properties and the device stability.

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): C07F15/00C07D401/04H01L51/54
Inventor 周明杰王平张娟娟梁禄生
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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