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Benzanthracene organic luminescent material, and preparation method and application thereof

A technology of light-emitting material and benzanthracene, which is applied in the preparation of light-emitting materials, organic compounds, organic chemistry, etc., can solve the problem that anthracene light-emitting materials cannot meet the requirements of OLED use, and can meet the needs of industrial development, high purity, The effect of improving solubility

Active Publication Date: 2014-05-21
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In order to solve the technical problem that the anthracene-based light-emitting materials in the prior art cannot meet the use requirements of OLEDs, the present invention provides a benzanthracene-based organic light-emitting device with simple preparation method, high luminous efficiency, long service life and good film-forming performance. Materials and their preparation methods and applications

Method used

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  • Benzanthracene organic luminescent material, and preparation method and application thereof
  • Benzanthracene organic luminescent material, and preparation method and application thereof
  • Benzanthracene organic luminescent material, and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: the synthesis of compound 001

[0030] The specific synthetic route is shown in the following formula:

[0031]

[0032] Under the condition of nitrogen protection, add 10.81g of phenylenediamine, 47.10g of bromobenzene, 0.75g of tris(dibenzylideneacetone)dipalladium, 2,2,-bis(diphenylphosphine)-1,1 into a 300ml single-necked bottle ,-binaphthyl (BINAP) 1.05g, potassium tert-butoxide 10.5g, dehydrated toluene 200ml, react at 85°C for 6 hours. After cooling, the reaction solution was filtered, and the obtained crude product was purified by silica gel chromatography, and dried under reduced pressure to obtain 24.73 g of a white solid intermediate.

[0033] Weigh 92.11g of benzanthracene bromine substitutes, 24.73g of white solid intermediate, 12.32g of potassium tert-butoxide, 0.56g of palladium (II) acetate, 0.51g of tri-tert-butylphosphine, add 250ml of dehydrated toluene, at 85℃ Reaction for 7 hours. The reaction solution was filtered, the crude pro...

Embodiment 2

[0034] Embodiment 2: the synthesis of compound 002

[0035] The specific synthetic route is shown in the following formula:

[0036] Under the condition of nitrogen protection, add 18.40g of phenylenediamine, 47.10g of bromobenzene, 1.50g of tris(dibenzylideneacetone)dipalladium, 2,2,-bis(diphenylphosphine)-1, 2.1 g of 1,-binaphthyl (BINAP), 21.1 g of potassium tert-butoxide, and 200 ml of dehydrated toluene were reacted at 86° C. for 7 hours. After cooling, the reaction solution was filtered, and the obtained crude product was purified by silica gel chromatography, and dried under reduced pressure to obtain 30.27 g of a white intermediate.

[0037] Weigh 92.11g of benzanthracene bromine substitute, 30.27g of white intermediate, 12.32g of potassium tert-butoxide, 0.56g of palladium(II) acetate, 0.51g of tri-tert-butylphosphine, add 250ml of dehydrated toluene, and react at 86°C 8 hours. The reaction solution was filtered, the crude product obtained was purified by silica ...

Embodiment 3

[0038] Embodiment 3: the synthesis of compound 003

[0039] The specific synthetic route is shown in the following formula:

[0040]

[0041]Under the condition of nitrogen protection, add 15.82g of naphthalene diamine, 47.10g of bromobenzene, 1.50g of tris(dibenzylideneacetone)dipalladium, 2,2,-bis(diphenylphosphine)-1,1 into a 300ml one-port bottle 2.1 g of -binaphthyl (BINAP), 21.1 g of potassium tert-butoxide, and 200 ml of dehydrated toluene were reacted at 86°C for 6 hours. After cooling, the reaction solution was filtered, and the obtained crude product was purified by silica gel chromatography, and dried under reduced pressure to obtain 28.56 g of a white intermediate.

[0042] Weigh 92.11g of benzanthracene bromine substitute, 28.56g of white intermediate, 12.32g of potassium tert-butoxide, 0.56g of palladium(II) acetate, 0.51g of tri-tert-butylphosphine, add 250ml of dehydrated toluene, and react at 87°C 7 hours. The reaction solution was filtered, the crude pr...

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Abstract

The invention relates to a benzanthracene organic luminescent material, and a preparation method and application thereof. The invention solves the technical problems that the anthracene luminescent material in the prior art can not satisfy the operating requirement for OLEDs (organic light-emitting diodes). The benzanthracene organic luminescent material provided by the invention is prepared by reacting R1 / R2-substituted diamine compound, R2-substituted halide and benzanthracene bromine substitute. Due to the introduction of the substituted group, the material has the advantages of higher solubility and favorable film-forming properties. The preparation method provided by the invention has the advantages of simple synthesis and purification processes and low cost, and can satisfy the demands of industrialization. Compared with the device prepared by using arylamino-substituted anthracene as the luminescent layer, the device prepared from the material provided by the invention has obviously higher luminescence efficiency and longer half-time service life; the luminescence efficiency is 26 Lm / w, and the half-time service life is 20000 hours; and thus, the material can satisfy the operating requirements for OLEDs.

Description

technical field [0001] The invention relates to the field of organic photoelectric materials, in particular to a benzanthracene-based organic light-emitting material and its preparation method and application. Background technique [0002] Compared with the existing liquid crystal and plasma flat panel display technology, organic electroluminescent display technology has many advantages such as simple structure, active light emission, high brightness, high efficiency, large viewing angle, fast response speed, and low-voltage DC drive. Organic light-emitting diode (OLED), as a new generation of flat panel display technology, has great market potential and competitiveness. In OLED research, materials play a decisive role. The materials used in OLED mainly include hole injection materials, hole transport materials, luminescent materials, electron transport materials and electron injection materials. The luminescent material is one of the main materials. Many research institu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07C211/61C07C209/10H01L51/54
Inventor 马晓宇李文军刘成凯
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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