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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, applied in the field of organic electroluminescent materials, can solve problems such as poor blue light color purity, achieve the effects of reducing self-quenching phenomenon, facilitating evaporation, and improving luminescent performance

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

[0040] see figure 1 , the preparation method of the above-mentioned blue light organic electrophosphorescent material iridium metal complex, comprising the following steps:

[0041] S1. Under 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 an organic solvent containing a catalyst and a base, and then the Suzuki coupling reaction is carried out at a temperature of 80-100 °C for 5-15 hours. After the reaction is stopped, the reaction solution is separated and purified to obtain the structural formula: Cyclometallic ligands; wherein, the molar ratio of compound A to compound B is 1:1~1:2; the reaction formula is:

[0042] S2. Under the protection of an inert gas, the cyclometal ligand and iridium trichloride trihydrate (IrCl 3 ·3H 2 O) Dissolve in a mixed solvent of 2-ethoxyethanol and water with a volume ratio of 3:1 at a molar ratio of 2:1 to 3:1, heat...

Embodiment 1

[0064] Example 1: Complex bis(3-(2',6'-difluoropyridin-3'-yl)pyridazine-N,C 2 ') (tetrakis (1-pyrazole) boron) synthesis of iridium

[0065] (1) Synthesis of 3-(2',6'-difluoropyridin-3'-yl)pyridazine:

[0066]

[0067] Under nitrogen protection, add 1.59g (10mmol) 3-bromopyridazine (A1), 1.91g (12mmol) 2,6-difluoropyridine-3-boronic acid (B), 40mL toluene, 10mL water, 1.61 g (5mmol) tetrabutylammonium bromide (TBTA), 1.38g (10mmol) anhydrous potassium carbonate, 0.23g (0.2mmol) tetrakis (triphenylphosphine) palladium, then stirred and refluxed at 80°C for 15h. 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, 1.27 g of solid was...

Embodiment 2

[0086] Example 2: Complex bis(3-(2',6'-difluoropyridin-3'-yl)pyridazine-N,C 2 ') Synthesis of (3-trifluoromethyl-5-(pyridin-2'-yl)-1,2,4-triazole) iridium

[0087] (1) The synthetic steps of 3-(2',6'-difluoropyridin-3'-yl)pyridazine refer to step (1) of Example 1;

[0088] (2) The synthesis steps of the iridium-containing dichloro dimer whose ligand is 3-(2',6'-difluoropyridin-3'-yl)pyridazine are the same as step (2) of Example 1;

[0089] (3) Complex bis(3-(2',6'-difluoropyridin-3'-yl)pyridazine-N,C 2 ') Synthesis of (3-trifluoromethyl-5-(pyridin-2'-yl)-1,2,4-triazole) iridium

[0090]

[0091] Under nitrogen protection, 0.64g (3mmol) 3-trifluoromethyl-5-(pyridin-2-yl)-1,2,4-triazole and 1.22g (1mmol) ligand were 3-(2', The iridium-containing dichloro dimer of 6'-difluoropyridin-3'-yl)pyridazine was dissolved in 60mL of chloroform, under the catalysis of 0.54g (10mmol) sodium methoxide, stirred and heated to reflux state, the reaction 24h. After naturally cooling to ...

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Abstract

The invention discloses a blue organic electrophosphorescent material iridium metal complex with a structural formula 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 is synthesized by taking 3-(2',6'-difluoropyridine-3'-yl)pyridazine or a derivative thereof as a cyclic metal ligand and tetra(1-pyrazole)boron and 3-trifluoromethyl-5-(2'-pyridyl)-1,2,4-triazole or 5-(2'-pyridyl)-1,2,3,4-tetrazole as an auxiliary ligand, thus obtaining emission of phosphorescence with bluer light emitting wavelength. The invention also provides a preparation method of the material and an organic electroluminescent device comprising the material.

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 周明杰王平张娟娟陈吉星
Owner OCEANS KING LIGHTING SCI&TECH CO LTD