Silicious benzanthracene organic electroluminescent material, and preparation method and application thereof

A benzanthracene and luminescent technology, which is applied in the direction of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems that blue light materials cannot meet the development requirements of industrialization, and achieve high yield, improved solubility, and film formation good performance 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 problem that blue light materials in the prior art cannot meet the development requirements of industrialization, the present invention provides a silicon-containing benzanthracene-based organic capacitor with simple preparation method, high luminous efficiency, good film-forming performance and long service life. Luminescent material and its preparation method and application

Method used

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  • Silicious benzanthracene organic electroluminescent material, and preparation method and application thereof
  • Silicious benzanthracene organic electroluminescent material, and preparation method and application thereof
  • Silicious benzanthracene organic electroluminescent material, and preparation method and application thereof

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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] Weigh 16.97g of silicon-containing benzanthracene bromine substitute, 42.05g of N-phenyl-2-carbazolylphenylamine, 12.32g of potassium tert-butoxide, 0.56g of palladium (II) acetate, tri-tert-butyl Phosphorus 0.51g was dissolved in 250ml of toluene, and reacted at 80°C for 6 hours under nitrogen protection. The reaction solution was filtered, the obtained crude product was purified by silica gel chromatography, and the obtained solid was recrystallized with toluene. After drying, 27.86 g of yellow-white solid compound 001 was obtained, with a yield of more than 94% and an HPLC purity of more than 98%. Mass spectrum: calculated value 592.80; found value 592.78. Elemental analysis: Calculated value: C: 85.10%; H: 5.44%; N: 4.73%; Si: 4.74%; Tested value: C: 85.10%; H: 5.44%; N: 4.73%; Si: 4.74%.

Embodiment 2

[0036] Embodiment 2: the synthesis of compound 002

[0037] The specific synthetic route is shown in the following formula:

[0038] Weigh 16.97g of silicon-containing benzanthracene bromine substituent, 45.15g of N-phenyl-2-carbazolyl-p-biphenylamine, 12.32g of potassium tert-butoxide, 0.56g of palladium (II) acetate, tri-tert-butyl 0.51 g of base phosphorus was dissolved in 250 ml 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, and the obtained solid was recrystallized with toluene. After drying, 31.43 g of yellow-white solid compound 002 was obtained, with a yield of more than 94% and an HPLC purity of more than 98%. Mass spectrum: calculated value 668.90; found value 668.88. Elemental analysis: calculated value C: 86.19%; H: 5.42%; N: 4.19%; Si: 4.20%; tested value C: 86.17%; H: 5.43%; N: 4.21%; Si: 4.19%.

Embodiment 3

[0039] Embodiment 3: the synthesis of compound 003

[0040] The specific synthetic route is shown in the following formula:

[0041]

[0042] Weigh 16.97g of silicon-containing benzanthracene bromine substitute, 46.38g of N-phenyl-2-carbazolylnaphthylamine, 12.32g of potassium tert-butoxide, 0.56g of palladium (II) acetate, tri-tert-butyl Phosphorus 0.51g was dissolved in 250ml of toluene, and reacted at 89°C for 8 hours under nitrogen protection. The reaction solution was filtered, the obtained crude product was purified by silica gel chromatography, and the obtained solid was recrystallized from toluene. After drying, 29.89 g of yellow-white solid compound 003 was obtained, with a yield of more than 93% and an HPLC purity of more than 98%. Mass Spectrum: Calculated 642.86; Tested 642.84. Elemental analysis: Calculated value: C: 85.94%; H: 5.33%; N: 4.36%; Si: 4.37%; Test value: C: 85.92%; H: 5.34%; N: 4.36%; Si: 4.38%.

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Abstract

The invention relates to a silicious benzanthracene organic electroluminescent material, and a preparation method and application thereof. The invention solves the technical problem that the blue light material in the prior art can not satisfy the requirement of industrialized development. The silicious benzanthracene organic electroluminescent material provided by the invention is an R1/R2-substituted silicious benzanthracene compound prepared by reacting R1/R2-substituted amine compound and silicious benzanthracene bromine substitute. Due to the introduction of substituted groups, the material has the advantages of higher solubility, favorable film-forming properties and higher luminescence efficiency, and is suitable for manufacturing an OLED (organic light-emitting diode) device. The material has the characteristics of simple preparation method, low cost and higher yield, and is easy to purify. The 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 silicon-containing benzanthracene 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 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 li...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F7/10H01L51/54
Inventor 马晓宇王辉秦亮
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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