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Green organic electroluminescent material and preparation method thereof

An electroluminescence and electromechanical technology, which is applied in the fields of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problem that the luminous efficiency of luminescent materials cannot meet the requirements of OLED, and achieves improved yield, high purity, and simple synthesis and purification. Effect

Active Publication Date: 2014-02-19
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Abstract
  • Description
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Problems solved by technology

[0004] In order to solve the technical problem that the luminous efficiency of the existing luminescent materials still cannot meet the requirements of OLEDs, the present invention provides a benzoacridine-based, green organic electroluminescent material with high luminous efficiency and a preparation method thereof

Method used

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  • Green organic electroluminescent material and preparation method thereof
  • Green organic electroluminescent material and preparation method thereof
  • Green organic electroluminescent material and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: the synthesis of compound 001

[0028] Concrete synthetic route is as follows:

[0029]

[0030] Weigh 23.12g of 3-methyl-7H-benzoacridine, 42.17g of 2-bromopyrene, 16.83g of potassium tert-butoxide, 1.13g of palladium(II) acetate, and 1.02g of tri-tert-butylphosphine, and dissolve them in 250ml of toluene , and reacted at 80° C. for 10 hours under the protection of nitrogen. The reaction solution was filtered, and the crude product obtained was purified by silica gel chromatography, and the obtained solid crude product was recrystallized with toluene and dried to obtain yellow-white 7-(2-pyrenyl)-3-methyl-7H-benzoacridine Pyridine 35.81g, the yield was 83%.

[0031] Under the protection of argon, 7-(2-pyrenyl)-3-methyl-7H-benzoacridine 35.81g, ammonia water 36.75g, palladium 0.76g, titanium dioxide photocatalyst, to obtain 7-(2-pyrenyl) -7H-Benzacridin-3-amine 30.51g, yield 85%.

[0032] Under the protection of nitrogen, 15.14g of 7-(2-pyrenyl)-7H-...

Embodiment 2

[0033]Embodiment 2: the synthesis of compound 002

[0034] Concrete synthetic route is as follows:

[0035]

[0036] Weigh 23.12g of 3-methyl-7H-benzoacridine, 42.17g of 2-bromopyrene, 16.83g of potassium tert-butoxide, 1.13g of palladium(II) acetate, and 1.02g of tri-tert-butylphosphine, and dissolve them in 250ml of toluene , and reacted at 80° C. for 10 hours under the protection of nitrogen. The reaction solution was filtered, and the crude product obtained was purified by silica gel chromatography, and the obtained solid crude product was recrystallized with toluene and dried to obtain yellow-white 7-(2-pyrenyl)-3-methyl-7H-benzoacridine Pyridine 35.81g, the yield was 83%.

[0037] Under the protection of argon, 7-(2-pyrenyl)-3-methyl-7H-benzoacridine 35.81g, ammonia water 36.75g, palladium 0.76g, titanium dioxide photocatalyst, to obtain 7-(2-pyrenyl) -7H-Benzacridin-3-amine 30.51g, yield 85%.

[0038] Under nitrogen protection, 15.14g of 7-(2-pyrenyl)-7H-benzoacr...

Embodiment 3

[0039] Embodiment 3: the synthesis of compound 003

[0040] Concrete synthetic route is as follows:

[0041]

[0042] Weigh 23.12g of 3-methyl-7H-benzoacridine, 58.35g of 4-bromotriphenylamine, 21.54g of potassium tert-butoxide, 1.74g of palladium (II) acetate, 1.56g of tri-tert-butylphosphine, and use 250ml of toluene Dissolve and react at 85°C for 13 hours under the protection of nitrogen. The reaction solution was filtered, and the obtained crude product was purified by silica gel chromatography, and then the obtained solid crude product was recrystallized with toluene and dried to obtain the yellow-white intermediate 7-(4-triphenylamino)-3-methyl-7H- Benzacridine 40.34g, yield 85%.

[0043] Under the protection of argon, 7-(2-pyrenyl)-3-methyl-7H-benzoacridine 40.34g, ammonia water 37.88g, palladium 0.78g, titanium dioxide photocatalyst, to obtain 7-(2-pyrenyl) -7H-Benzacridin-3-amine 33.45 g, yield 85%.

[0044] Under nitrogen protection, 16.72g of 7-(4-triphenylam...

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Abstract

The invention relates to a green organic electroluminescent material and a preparation method thereof, and solves the technical problem that the luminous efficiency of an existing luminous material still cannot meet the requirements of OLEDs (organic light-emitting diodes). According to the green organic electroluminescent material, 3-methyl-7H-benzacridine and R1 bromide are taken as raw materials and react to obtain a benzacridine compound containing an R1 substituent group, the benzacridine compound is subjected to a reducing process by palladium carbon to obtain a benzacridine amine compound containing the R1 substituent group, and the benzacridine amine compound continues to react with R2 bromide to obtain a benzacridine amine compound containing R1 and R2 substituent groups. Due to introduction of different substituent groups, electron transition can be adjusted to adjust luminous peak so as to obtain the required green organic electroluminescent material. According to the preparation method provided by the invention, synthesis and purification processes are simpler, the cost is low, and the industrialization development requirements can be met.

Description

technical field [0001] The invention relates to the field of organic photoelectric materials, in particular to a green organic electroluminescence material and a preparation method thereof. Background technique [0002] Organic electroluminescence refers to the phenomenon that organic materials are excited by electric current and electric field to emit light under the action of electric field. Organic light-emitting diodes (OLEDs) are a next-generation display technology that utilizes this phenomenon to realize displays. In OLED research, the choice of organic materials plays a decisive role. The organic materials used in OLED mainly include hole injection materials, hole transport materials, luminescent materials, electron transport materials and electron injection materials, among which luminescent materials are the main materials. Many research institutions and enterprises at home and abroad have done a lot of research work to continuously improve the comprehensive perf...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D221/18C07D401/04
Inventor 马晓宇李文军张英李贺
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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