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Red organic electroluminescent material and its preparation method and application

A luminescent and electromechanical technology, applied in the direction of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of color purity and backwardness that are rarely achieved in deep red and dark green light, and reduce self-quenching Phenomenon, reduction of direct action, effect of improving electroluminescent performance

Inactive Publication Date: 2014-08-06
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

Generally speaking, the development of blue phosphorescent materials always lags behind red light and green light. In terms of color purity alone, blue phosphorescent materials have rarely been able to achieve the same level as deep red light and deep green light. color purity

Method used

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  • Red organic electroluminescent material and its preparation method and application
  • Red organic electroluminescent material and its preparation method and application
  • Red organic electroluminescent material and its preparation method and application

Examples

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preparation example Construction

[0037] The preparation method of the above-mentioned red light organic electroluminescent material comprises the following steps:

[0038] S1. Under the protection of inert gas (at least one of nitrogen and argon, the same below), the structural formula is Compound A (2,5-dibromopyridine) and the structural formula is Compound B (4-triphenylamine boronic acid) was dissolved in tetrakis(triphenylphosphine) palladium (Pd(PPh 3 ) 4 ) or dichlorobistriphenylphosphine palladium (Pd(PPh 3 ) 2 Cl 2) in an organic solvent of catalyst and alkali, and then reflux the Suzuki coupling reaction at a temperature of 63-120°C for 6-10 hours. After the reaction stops, the reaction liquid is separated and purified to obtain the structural formula: Compound C (2-(triphenylamine-4'-yl)-5-bromopyridine); wherein, the molar ratio of compound A to compound B is 1:1.2; the molar ratio of catalyst to compound A is 0.05:1; base The molar ratio with compound A is 10:3; Reaction formula is as fo...

Embodiment 1

[0065] Example 1: Complex bis[2-(triphenylamine-4'-yl)-5-benzoylpyridine-N,C 2 Synthesis of '](acetylacetonate) iridium

[0066] (1) Synthesis of 2-(triphenylamine-4'-yl)-5-bromopyridine

[0067]

[0068] 0.71g (3.0mmol) 2,5-dibromopyridine, 1.04g (3.6mmol) 4-triphenylamine boronic acid, 0.17g (0.15mmol) tetrakis(triphenylphosphine)palladium, 25mL toluene, 12.5mL ethanol and 5mL concentration 2M sodium carbonate (10.0 mmol) aqueous solution was refluxed at 120°C for 6h. After the reaction was cooled to room temperature, it was poured into an appropriate amount of distilled water and extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate. Filter and evaporate the solvent to obtain the crude product. The crude product was purified by silica gel column chromatography using a mixture of ethyl acetate and n-hexane with a volume ratio of 3:1 as the eluent to obtain 0.90 g of a white solid with a yield of 74.8%.

[0069] Structure Identific...

Embodiment 2

[0098] Example 2: Complex bis[2-(triphenylamine-4'-yl)-5-(naphthalene-1'-formyl)pyridine-N,C 2 Synthesis of '](acetylacetonate) iridium

[0099] (1) The synthesis steps of 2-(triphenylamine-4'-yl)-5-bromopyridine are the same as in Example 1, except that the Suzuki coupling reaction is refluxed at 80°C for 9 hours;

[0100] (2) Synthesis of 2-(triphenylamine-4'-yl)-5-(naphthalene-1'-formyl)pyridine

[0101]

[0102] Under the protection of argon, 1.60 g (4.0 mmol) of 2-(triphenylamine-4'-yl)-5-bromopyridine was dissolved in 20 mL of freshly distilled ether, and the temperature of the reaction system was lowered to -78°C under stirring. 4 mL of 1.6 M n-butyllithium (6.4 mmol) n-hexane solution was added dropwise with a syringe, the addition was completed within 10 min, and stirring was continued at -78°C for 35 min. 1.20g (6.0mmol) of N,N-dimethyl-naphthalen-1'-ylformamide was dissolved in 20mL of freshly distilled ether, and added dropwise to the reaction system within 5m...

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Abstract

The invention belongs to the organic electroluminescent material, and discloses a red organic electroluminescent material and a preparation method and application thereof. The material has a general structural formula as follows, wherein R represents phenyl, naphthyl-1-yl or naphthyl-2-yl. The red organic electroluminescent phosphorescent material provided by the invention uses 2-(triphenylamine-4'-yl)-5-aryl formyl pyridine as a main structure of a ring metal ligand, and the introduction of phenyl, naphthyl-1-yl and naphthyl-2-yl formyl realizes acquisition of satisfactory red emission wavelength; the presence of large groups such as triphenylamine, phenyl or naphthyl can produce a certain space steric effect, thereby reducing the direct interaction between metal atoms, and reducing self quenching phenomenon of triplet exciton; at the same time, aromatic groups can effectively control the energy levels of highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) of the material, and facilitate the balance of charge transfer in a device, so as to improve the luminescent properties of the device.

Description

technical field [0001] The invention relates to an organic electroluminescent material, in particular to a red light organic electroluminescent material and a preparation method and application thereof. 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 new prelude to the research on organic electrol...

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
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