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Novel electroluminescent material and applications thereof

A technology of electroluminescent materials and luminescent materials, applied in the direction of luminescent materials, condensation/addition reactions to prepare amino compounds, chemical instruments and methods, etc., can solve the problems that luminescent materials cannot meet the requirements of OLEDs, and achieve a good planar structure Effects of conjugated system, life improvement, and solubility improvement

Active Publication Date: 2015-05-20
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • 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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  • Novel electroluminescent material and applications thereof
  • Novel electroluminescent material and applications thereof
  • Novel electroluminescent material and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: the synthesis of compound 001

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

[0036]

[0037] 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.

[0038] 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

[0040] Embodiment 2: the synthesis of compound 002

[0041] The specific synthetic route is shown in the following formula:

[0042]

[0043] 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.

[0044] 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

[0046] Embodiment 3: the synthesis of compound 003

[0047] The specific synthetic route is shown in the following formula:

[0048]

[0049] 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.

[0050] 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, and aims to solve the technical problem that the luminescent efficiency of conventional luminescent materials cannot fulfill the requirements of OLED. The novel organic electroluminescent material is prepared by introducing diamine compounds with different substituents into a base material (indenofluorene compounds) so as to connect the indenofluorene molecules together. The steric hindrance of introduced substituents prevents the molecules from going near to each other, thus the film-forming performance of the material is improved, and the dissolving property of the material is improved at the same time. The luminescent efficiency of the provided material in a diluted solution is 97%, the luminescent efficiency in film is 81%, and the results show that the indenofluorene compounds have high luminescent efficiency. Compared with 2-bromo-5,5,10,10,15,15-hexaethyl-10,15-dihydro-5H-indenofluorene, the provided preparation method of indenofluorene organic electroluminescent material has the advantages of simpler synthesis and purification, and lower cost, and is capable of fulfilling the industrial development requirements. The product yield is largely improved, the product purity is high, the HPLC purity is greater than 98%, the obtained material can prominently improve the efficiency, and the film-forming property and service life of the obtained material are both improved obviously.

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 Applications(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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