Benzanthracene organic electroluminescent material, and preparation method and application thereof

A benzanthracene and luminescent technology, which is applied in the direction of luminescent materials, preparation of organic compounds, organic chemistry, etc., can solve the problems of short lifespan and low luminous efficiency, and achieve the goals of increased yield, low preparation cost and optimized reaction conditions Effect

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 technical problems of low luminous efficiency and short service life of blue light materials in the prior art, the present invention provides a benzanthracene-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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  • Benzanthracene organic electroluminescent material, and preparation method and application thereof
  • Benzanthracene organic electroluminescent material, and preparation method and application thereof
  • Benzanthracene organic electroluminescent material, and preparation method and application thereof

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Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1: the synthesis of compound 001

[0036] The specific synthetic route is shown in the following formula:

[0037] Weigh 16.16g of 3-bromo-7,7-dimethyl-7H-benzoanthracene, 42.05g of N-phenyl-2-carbazolylphenylamine, 12.32g of potassium tert-butoxide, and palladium(II) acetate 0.56g and 0.51g of tri-tert-butylphosphine were dissolved in 250ml of toluene and reacted at 85°C for 7 hours under the protection of nitrogen. The reaction solution was filtered, the obtained crude product was purified by silica gel chromatography, and the obtained solid was recrystallized with toluene and dried to obtain 27.39 g of yellow-white solid compound 001 with a yield of more than 95% and an HPLC purity of more than 98%. Mass Spectrum: Calculated 576.23; Found 576.24. Elemental analysis: calculated value C: 89.55%; H: 5.59%; N: 4.86%; tested value C: 89.52%; H: 5.60%; N: 4.87%.

Embodiment 2

[0038] Embodiment 2: the synthesis of compound 002

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

[0040] Weigh 16.16g of 3-bromo-7,7-dimethyl-7H-benzanthracene, 45.15g of N-phenyl-2-carbazolyl p-biphenylamine, 12.32g of potassium tert-butoxide, palladium acetate (II ) 0.56g, tri-tert-butylphosphine 0.51g, dissolved in 250ml of toluene, and reacted at 86°C for 8 hours under the protection of nitrogen. The reaction solution was filtered, the obtained crude product was purified by silica gel chromatography, the obtained solid was recrystallized with toluene, and dried to obtain 30.03 g of yellow-white solid compound 002 with a yield of more than 92% and an HPLC purity of more than 98%. Mass Spectrum: Calculated 652.82; Asserted 652.80. Elemental analysis: calculated value C: 90.15%; H: 5.56%; N: 4.29%; tested value C: 90.13%; H: 5.57%; N: 4.30%.

Embodiment 3

[0041] Embodiment 3: the synthesis of compound 003

[0042] The specific synthetic route is shown in the following formula:

[0043]

[0044]Weigh 16.16g of 3-bromo-7,7-dimethyl-7H-benzanthracene, 46.38g of N-phenyl-2-carbazolylnaphthylamine, 12.32g of potassium tert-butoxide, and palladium(II) acetate 0.56g and 0.51g of tri-tert-butylphosphine were dissolved in 250ml of toluene, and reacted at 88°C for 8 hours under the protection of nitrogen. The reaction solution was filtered, the obtained crude product was purified by silica gel chromatography, the obtained solid was recrystallized with toluene, and dried to obtain 29.15 g of yellow-white solid compound 003 with a yield of more than 93% and an HPLC purity of more than 98%. Mass Spectrum: Calculated 461.60; Found 461.58. Elemental analysis: calculated value C: 91.07%; H: 5.90%; N: 3.03%; tested value C: 91.05%; H: 5.91%; N: 3.04%.

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Abstract

The invention relates to a benzanthracene organic electroluminescent material, and a preparation method and application thereof. The invention solves the technical problems of low efficiency and short service life in the blue light material in the prior art. The benzanthracene organic electroluminescent material provided by the invention is prepared by reacting R1 / R2-substituted amine compound and 3-bromo-7,7-dimethyl-7H-benzanthracene. Due to the introduction of substituted groups, the material has the advantages of higher solubility and favorable film-forming properties, and is suitable for manufacturing an OLED (organic light-emitting diode) device. The preparation method of the material is simple and low in cost; and the toxic solvent used in the past organic material preparation process is changed into the common solvent methylbenzene, so that the operation is convenient, the product is easy to purify, and the yield is higher. The benzanthracene organic electroluminescent material can be used as a luminescent material, luminescent main body material or transmission material in an electroluminescent device, and has wide prospects.

Description

technical field [0001] The invention relates to the field of organic photoelectric materials, in particular to a benzanthracene-based organic electroluminescent material and its preparation method and application. Background technique [0002] After ten years of development, organic electroluminescent devices (OLEDs) have become the most powerful contenders for next-generation flat-panel display devices. Compared with liquid crystal flat-panel displays, organic electroluminescent flat-panel displays (OLEDs) 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 red, green and blue three-primary color luminescent materials, green and red materials have reached or approached practical requirements in terms of efficiency and lifespan. In contrast, blue light m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D209/88C07C211/61C07C209/10H01L51/54
Inventor 马晓宇王辉李国强
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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