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Organic electroluminescent material, preparation method of organic electroluminescent material and organic electroluminescent device

An electroluminescence, electromechanical technology, applied in the field of phosphorescent materials, can solve the problems of blue shift of luminescence wavelength, HOMO energy level drop, luminescence color purity of blue-light phosphorescence materials, efficiency attenuation bottleneck of luminous efficiency devices, etc.

Inactive Publication Date: 2015-04-29
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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Problems solved by technology

[0006] Although various optimizations have been made to the FIrpic OLED structure, and the device performance has been greatly improved, 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. The CIE of each OLED device produced It varies between (0.13~0.17,0.29~0.39), which is a big gap with the standard Blu-ray CIE (0.137,0.084)
[0007] In 2009, Youngjin Kang et al. from South Korea reported a blue phosphorescent material containing iridium complexes with bipyridine as the main structure of the ring metal ligand—three (2′,6′-difluoro-2,3′-bipyridine ) Iridium Ir(dfpypy) 3 [Inorg.Chem.2009,48,1030-1037.], because N atoms are directly used to replace CH on the benzene ring, the electronegativity of N is stronger than that of C, which leads to a further decrease in the HOMO energy level of the material, and a blue shift in the emission wavelength
[0011] People's research on iridium metal complexes of organic electroluminescent materials has been in-depth, but there are bottlenecks in the luminous color purity, luminous efficiency and device efficiency attenuation of blue phosphorescent materials.

Method used

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  • Organic electroluminescent material, preparation method of organic electroluminescent material and organic electroluminescent device
  • Organic electroluminescent material, preparation method of organic electroluminescent material and organic electroluminescent device
  • Organic electroluminescent material, preparation method of organic electroluminescent material and organic electroluminescent device

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preparation example Construction

[0047] The preparation process of the organic electroluminescent material (P) of the present invention is roughly divided into the following steps:

[0048] (1) Synthesize compound C from compound E and compound F through Suzuki coupling reaction; wherein, compound F is 2,6-

[0049] Difluoropyridine-3-boronic acid, the structural formulas of compound E and compound C are as follows:

[0050] Compound E is Compound C is Among them, R 1 is a hydrogen atom, C 1～20 straight chain alkyl, C 1～20 Branched chain alkyl, C 1～20 straight chain alkoxy or C 1～20 branched chain alkoxy.

[0051] (2) Reaction of compound C prepared in step (1) with compound D to generate a chlorine-bridged dimer, namely compound A. Wherein, compound D is trihydrate iridium trichloride IrCl 3 ·3H 2 O. The structural formula of compound A is as follows:

[0052]

[0053] (3) Compound A prepared in step (2) is used as a ring metal ligand, and compound B is used as an auxiliary ligand source to ...

Embodiment 1

[0058] The organic electroluminescent material (P) disclosed in this example is the complex bis(2-(2′,6′-difluoropyridin-3′-yl)pyrimidine-N,C 4′ ) (acetylacetonate) iridium, its structural formula is as follows:

[0059]

[0060] It is prepared by the following steps:

[0061] (1) Synthesis of 2-(2′,6′-difluoropyridin-3′-yl)pyrimidine

[0062] The synthetic reaction formula of 2-(2',6'-difluoropyridin-3'-yl)pyrimidine is as follows:

[0063]

[0064] The specific steps are: under nitrogen atmosphere, 1.59g (10mmol) 2-bromopyrimidine, 1.91g (12mmol) 2,6-difluoropyridine-3-boronic acid and 0.58g (0.5mmol) tetrakis (triphenylphosphine) palladium Dissolve in 40ml of toluene, then add dropwise 20ml of a solution containing 2.76g (20mmol) of potassium carbonate to the reaction system. Heat to 100°C and stir the reaction for 8h. After the reaction solution was cooled to room temperature, it was extracted with dichloromethane, separated, washed with water until neutral, and ...

Embodiment 2

[0080]The organic electroluminescent material disclosed in this example is the complex bis(2-(2′,6′-difluoropyridin-3′-yl)-5-methylpyrimidine-N,C 4′ ) (acetylacetonate) iridium, its structural formula is as follows:

[0081]

[0082] It is prepared by the following steps:

[0083] (1) Synthesis of 2-(2′,6′-difluoropyridin-3′-yl)-5-methylpyrimidine

[0084] The reaction formula for the synthesis of 2-(2′,6′-difluoropyridin-3′-yl)-5-methylpyrimidine is as follows:

[0085]

[0086] The specific steps are: under nitrogen atmosphere, 1.73g (10mmol) 2-bromo-5-methylpyrimidine, 1.59g (10mmol) 2,6-difluoropyridine-3-boronic acid and 0.28g (0.4mmol) dichlorobis (Triphenylphosphine)palladium was dissolved in 50ml of DMF, and then 25ml of sodium carbonate solution containing 3.18g (30mmol) was added dropwise to the reaction system. Stir the reaction under heating to 90°C for 10 h. After the reaction solution was cooled to room temperature, it was extracted with dichloromethane...

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Abstract

The invention provides an organic electroluminescent material, a preparation method of the organic electroluminescent material and an organic electroluminescent device. The organic electroluminescent material has a general formula (P) as shown in the specification, wherein R1 is hydrogen atom, C1-20 linear alkyl, C1-20 branched alkyl, C1-20 linear alkoxy or C1-20 branched alkoxy. According to the organic electroluminescent material, 2-(2',6'-difluoro-3'-yl) pyrimidine serving as a cyclometalated ligand and acetylacetone serving as an auxiliary ligand are adopted to synthesize a blue-light organic electroluminescent material iridium heterotropic complex, and the illuminating color of the material is adjusted through chemical modification performed by introducing alkyl or alkoxy chain on the pyrimidine ring of the cyclometalated ligand, so that phosphorescence emission having high luminescence efficiency can be obtained.

Description

technical field [0001] The invention relates to the field of phosphorescent materials, in particular to an organic electroluminescent material. The invention also relates to the preparation method of the organic electroluminescent material and its application in organic electroluminescent devices. 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 brightnes...

Claims

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Application Information

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