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A New Electroluminescent Material and Its Application

An electroluminescent material and luminescent technology, applied in the direction of luminescent materials, condensation/addition reaction preparation of amino compounds, chemical instruments and methods, etc., can solve the problems that luminescent materials cannot meet the requirements of OLED, and achieve a good planar structure and conjugated systems, improved lifetime, and simple synthesis and purification

Active Publication Date: 2017-01-04
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In order to solve the technical problem that indenofluorene light-emitting materials in the prior art cannot meet the use requirements of OLEDs, the present invention provides an indenofluorene-based organic electroluminescent material with simple preparation method, high luminous efficiency and long service life And its preparation method and application

Method used

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  • A New Electroluminescent Material and Its Application
  • A New Electroluminescent Material and Its Application
  • A New Electroluminescent Material and Its Application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1: the synthesis of compound 001

[0034] The specific synthetic route is shown in the following formula:

[0035]

[0036] 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.

[0037] 168.05g of 2-bromo-5,5,10,10,15,15-hexaethyl-10,15-dihydro-5H-indenofluorene, 24.73g of white solid intermediate, 21.32g of potassium tert-butoxide, 1.02 g of palladium (II) acetate, 0.97 g of tri-tert-butylphosphine, and 250 ml of dehydrated toluene were reacted at 85°C for 10 hours. The reaction so...

Embodiment 2

[0038] Embodiment 2: the synthesis of compound 002

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

[0040]

[0041]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, 2.1g of 1,-binaphthyl (BINAP), 21.1g of potassium tert-butoxide, and 200ml 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.

[0042] 173.65g of 2-bromo-5,5,10,10,15,15-hexaethyl-10,15-dihydro-5H-indenofluorene, 30.27g of white intermediate, 22.44g of potassium tert-butoxide, acetic acid 1.08 g of palladium (II), 1.01 g of tri-tert-butylphosphine, and 250 ml of dehydrated toluene were reacted at 86°C for 11 hours. The reaction solution was filtered, and ...

Embodiment 3

[0043] Embodiment 3: the synthesis of compound 003

[0044] The specific synthetic route is shown in the following formula:

[0045]

[0046] 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.

[0047] 2-Bromo-5,5,10,10,15,15-hexaethyl-10,15-dihydro-5H-indenofluorene 179.25g, white intermediate 28.56g, potassium tert-butoxide 23.56g, acetic acid 1.14 g of palladium (II), 1.06 g of tri-tert-butylphosphine, and 250 ml of dehydrated toluene were reacted at 87°C for 12 hours. The reaction s...

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Abstract

The invention relates to an organic electroluminescent material and a preparation method thereof, which solves the technical problem that the luminous efficiency of the existing luminescent material still cannot meet the requirements of OLEDs. Organic electroluminescent materials are based on indenofluorene compounds, a new class of organic light-emitting materials synthesized by linking indenofluorene compounds molecules together through diamine compounds containing different substituents. The steric hindrance of the introduced substituent prevents molecules from approaching in space to improve the film-forming performance, and the introduction of the substituent also improves the solubility of this type of material. The luminous efficiency of the material in the dilute solution is 97%, and the luminous efficiency in the thin film is 81%, indicating that the indenofluorene compound has high luminous efficiency. Compared with 2-bromo-5,5,10,10,15,15-hexaethyl-10,15-dihydro-5H-indenofluorene, the indenofluorene organic electroluminescent material provided by the present invention has The preparation method has relatively simple synthesis and purification, low cost, and can meet the needs of industrialization development. The yield of the product is greatly improved, and the purity is high, and the HPLC purity is greater than 98%. Moreover, the prepared material can significantly improve the efficiency, and have obvious improvements in film-forming performance and service life.

Description

technical field [0001] The invention relates to the field of organic photoelectric materials, in particular to an indenofluorene-based organic electroluminescence material and a preparation method and application thereof. Background technique [0002] Among many organic electroluminescent materials, compounds containing indenofluorene structures are important components. Indenofluorene compounds, like fluorene, have relatively rigid structures. In addition, these compounds also have good thermal stability. , High luminous efficiency and other advantages, therefore, both thermal stability and fluorescence quantum efficiency are good, it is an ideal precursor for the development of new OLED materials. [0003] Isotriindene is an isomer of triindene. Due to the difference in structure, the benzene rings of the two compounds are directly conjugated to each other and their names are different. Traditional synthetic methods are tedious and harsh to regulate, and the yield is low,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07C211/61C07C209/60
Inventor 马晓宇王辉赵贺李文军
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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