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Benzanthracene organic luminescent material, and preparation method and application thereof

A technology of luminescent materials and benzanthracene, which is applied in the fields of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of low cost and the inability of blue light materials to meet industrial production, and achieve easy processing, improved luminous efficiency, and film formation good performance

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

AI Technical Summary

Problems solved by technology

[0004] In order to solve the problem that the existing blue light materials cannot meet the requirements of industrial production, the present invention provides a benzanthracene-based organic light-emitting material with high luminous efficiency, low cost, high yield and purity, and its preparation method and application

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1: the synthesis of compound 001

[0031] The specific synthetic route is shown in the following formula:

[0032] Add 18.18g of 3,9-dibromo-7,7-dimethyl-7H-benzoanthracene, 11.30g of N-phenyl-2-carbazolylboronic acid, 20g of sodium carbonate, 250ml of tetrahydrofuran and 125ml of water into the three-necked flask , degassing, add 0.9g tetrakis(triphenylphosphine)palladium, heat up to 90°C, reflux for 24 hours, cool to room temperature, after the solid precipitates, suction filter, the filter cake is washed with water, ethanol and ether, and dried 30.32 g of 3,9-bis(N-phenylcarbazolyl)-7,7-dimethyl-7H-benzanthracene was obtained, with a yield of over 92% and an HPLC purity of over 98%. Mass Spectrum: Calculated 728.92; Found 728.90. Elemental analysis: Calculated for C: 90.63%; H: 5.53%; N: 3.84%; tested for C: 90.62%; H: 5.54%; N: 3.84%.

Embodiment 2

[0033] Embodiment 2: the synthesis of compound 002

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

[0035]

[0036] Add 18.18g of 3,9-dibromo-7,7-dimethyl-7H-benzoanthracene, 15.63g of 3-phenanthroline boronic acid, 20g of sodium carbonate, 250ml of tetrahydrofuran and 125ml of water into a three-necked flask, degas, Add 0.9g of tetrakis(triphenylphosphine)palladium, raise the temperature to 100°C, reflux for 27 hours, cool to room temperature, after the solid precipitates, filter with suction, wash the filter cake with water, ethanol and ether, and dry to obtain 3,9 - 25.26 g of bis(phenanthrolinyl)-7,7-dimethyl-7H-benzanthracene, the yield is over 93%, and the HPLC purity is over 98%. Mass Spectrum: Calcd. 600.71; Tested 600.69. Elemental analysis: calculated value C: 85.98%; H: 4.70%; N: 9.33%; tested value C: 85.96%; H: 4.72%; N: 9.32%.

Embodiment 3

[0037] Embodiment 3: the synthesis of compound 003

[0038] The specific synthetic route is shown in the following formula:

[0039]

[0040] Add 18.18g of 3,9-dibromo-7,7-dimethyl-7H-benzoanthracene, 11.30g of 5-benzofuranylboronic acid, 20g of sodium carbonate, 250ml of tetrahydrofuran and 125ml of water into a three-necked flask, degas, Add 0.9g of tetrakis(triphenylphosphine)palladium, raise the temperature to 100°C, reflux for 30 hours, cool to room temperature, after the solid precipitates, filter with suction, wash the filter cake with water, ethanol and ether, and dry to obtain 3,9 -Bis(benzofuryl)-7,7-dimethyl-7H-benzanthracene 19.40g, the yield is over 90%, and the HPLC purity is over 98%. Mass Spectrum: Calculated 476.56; Found 476.54. Elemental analysis: Calculated for C: 88.21%; H: 5.08%; O: 6.71%; tested for C: 88.20%; H: 5.07%; O: 6.72%.

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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 problem that the existing blue light material can not satisfy the industrial production. The organic luminescent material provided by the invention is a compound using benzanthracene as a basic framework. The organic luminescent material is prepared by carrying out Suzuki coupling reaction on 3,9-dibromo-7,7-dimethyl-7H-benzanthracene and boric acid containing A substituent group, and has the advantages of favorable film-forming properties and high luminescence efficiency. By changing the reaction solvent into a common solvent, the preparation method is convenient to operate and easy for purification, greatly enhances the yield, and lowers the cost, so that the compound has the possibility for further development and application and can satisfy the demands of industrial production. The material can be used as an organic luminescent material, luminescent main body material or transmission material in an electroluminescent device.

Description

technical field [0001] The invention belongs to the field of organic photoelectric materials, and in particular relates to a benzanthracene organic light-emitting material and its preparation method and application. Background technique [0002] The preparation and device design of new organic and polymer optoelectronic materials is a very active field in the world. Compared with liquid crystal flat-panel displays, organic and polymer electroluminescent flat-panel displays (OLEDs and PLEDs) have significant characteristics such as active light emission, no angle dependence, good contrast, light, thin, and low energy consumption, and have broad application prospects. The primary colors red, green, and blue are necessary for an effective full-color display. Among them, blue light materials can be used as doped host materials for red and green light materials due to their wide energy gaps. In addition, blue light can also obtain red light and green light through color convers...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D209/86C07D519/00C07D307/79C07C211/54C07C209/68C07C13/66C07C1/32H01L51/54
Inventor 马晓宇高巍巍刘成凯
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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