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Iridium-containing organic electroluminescent material, its preparation method and organic electroluminescent device

A luminescent and electromechanical technology, applied in the fields of luminescent materials, electric solid devices, organic chemistry, etc.

Inactive Publication Date: 2014-01-15
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the limitation of spin statistics theory, the theoretical internal quantum efficiency limit of fluorescent materials is only 25%. How to make full use of the remaining 75% of phosphorescence to achieve higher luminous efficiency has become a hot research direction in this field since then.

Method used

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  • Iridium-containing organic electroluminescent material, its preparation method and organic electroluminescent device
  • Iridium-containing organic electroluminescent material, its preparation method and organic electroluminescent device
  • Iridium-containing organic electroluminescent material, its preparation method and organic electroluminescent device

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preparation example Construction

[0039] The preparation method of the above-mentioned iridium-containing organic electroluminescent material comprises the following steps:

[0040] The following steps are carried out under anhydrous and anaerobic conditions unless otherwise specified, such as in N 2 Or under an inert gas atmosphere, etc., the solvent used can also adopt other solvents that have better compatibility with the reactants except the solvents given in each step.

[0041] S1, providing compound C and compound D represented by the following structural formula,

[0042]

[0043] S2. Under anhydrous and oxygen-free conditions, compound C and compound D are carried out in an organic solvent in a Suzuki reaction in a molar ratio of 1:1 to 1:2 under the condition of a catalyst, and compound A is obtained after purification. The reaction formula is as follows:

[0044]

[0045] In this step, preferably, the catalyst used in the Suzuki reaction is a cocatalyst composed of an inorganic base and an org...

Embodiment 1

[0059] Example 1: Complex three (2',6'-dichloro-2,3'-bipyridine-N,C 2 ’) Synthesis of iridium

[0060] 1. Synthesis of 2,6-dichloro-3,2'-bipyridine

[0061] Under nitrogen protection, (0.95g, 6.00mmol) 2-bromopyridine, (1.38g, 7.20mmol) 2,6-dichloro-3-pyridineboronic acid, (3.04g, 22mmol) K 2 CO 3 and (0.35g,0.30mmol)Pd(PPh 3 ) 4 Dissolve in a mixed solution of 30mL toluene and 5mL water, heat to 100°C, and stir for 20h. After cooling to room temperature, the aqueous phase in the reaction mixture was separated and extracted with ethyl acetate (3×100 mL), and the organic phases were combined. The combined organic phases were washed with brine and dried over anhydrous magnesium sulfate. Filter and evaporate the solvent to obtain the crude product. The mixture of chloroform and n-hexane with a volume ratio of 1:3 was used as the eluent for silica gel column chromatography to obtain 0.78 g of a white solid with a yield of 57.8%. The reaction equation is as follows:

[006...

Embodiment 2

[0072] Example 2: Complex three (2',6'-difluoro-2,3'-bipyridine-N,C 2 ’) Synthesis of iridium

[0073] 1. For the synthesis steps of 2,6-difluoro-3,2'-bipyridine, see Example 1

[0074] Under nitrogen protection, (0.95g, 6.00mmol) 2-bromopyridine, (1.14g, 7.20mmol) 2,6-difluoro-3-pyridineboronic acid, (3.04g, 22mmol) K 2 CO 3 and (0.35g,0.30mmol)Pd(PPh 3 ) 4 Dissolve in a mixed solution of 30mL toluene and 5mL water, heat to 100°C, and stir for 20h. After cooling to room temperature, the aqueous phase in the reaction mixture was separated and extracted with ethyl acetate (3×100 mL), and the organic phases were combined. The combined organic phases were washed with brine and dried over anhydrous magnesium sulfate. Filter and evaporate the solvent to obtain the crude product. The mixture of chloroform and n-hexane with a volume ratio of 1:3 was used as the eluent for silica gel column chromatography to obtain 0.69 g of a white solid with a yield of 59.8%. The reaction eq...

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Abstract

The invention relates to an iridium-containing organic electroluminescent material, which has a structural formula I as the following. Specifically, X is F or Cl, and Y is F or Cl. Additionally, a iridium-containing organic electroluminescent material molecule contains a bipyridine ligand, and the iridium-containing organic electroluminescent material molecule also has two halogen groups, so that the electron injection and transmitting capacity of the luminescent material can be improved, and the luminescent wavelength can achieve effective blueshift. Therefore, the organic phosphorescent material with iridium as the internal core can have high internal quantum efficiency and electroluminescent efficiency. In addition, the invention also relates to a preparation method of the iridium-containing organic electroluminescent material and an organic electroluminescent device.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence, in particular to an iridium-containing organic electroluminescence material, 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 n...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D213/61H01L51/54
Inventor 周明杰王平张娟娟钟铁涛
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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