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

A benzanthracene and luminescent technology, applied in the direction of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problem that anthracene luminescent materials cannot meet the requirements of OLED use, and meet the needs of industrial development and good planar structure and conjugated systems, synthesis and purification of simple effects

Active Publication Date: 2014-05-21
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0004] In order to solve the technical problem that anthracene-based luminescent materials in the prior art cannot meet the use requirements of OLEDs, the present invention provides a silicon-containing benzene compound with simple preparation method, high luminous efficiency, long service life and good film-forming performance. Anthracene organic electroluminescent 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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Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: the synthesis of compound 001

[0032] The specific synthetic route is shown in the following formula:

[0033] Weigh 16.97g of silicon-containing benzanthracene bromine substituents, 32.89g of 2-naphthylphenylamine, 12.32g of potassium tert-butoxide, 0.56g of palladium (II) acetate, 0.51g of tri-tert-butylphosphorus, and use 250ml Toluene was dissolved, and reacted at 80° C. for 5 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 31.96 g of yellow-white solid compound 001 with a yield of more than 92% and an HPLC purity of more than 98%. Mass spectrum: calculated value 694.94; found value 694.92. Elemental analysis: calculated value C: 86.42%; H: 5.51%; N: 4.03%; Si: 4.04%; tested value C: 86.40%; H: 5.52%; N: 4.02%; Si: 4.05%.

Embodiment 2

[0034] Embodiment 2: the synthesis of compound 002

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

[0036]

[0037] Weigh 16.97g of silicon-containing benzanthracene bromine substitute, 53.50g 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 85°C for 7 hours. 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 42.56 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 925.20; Asserted 925.23. Elemental analysis: calculated value C: 85.68%; H: 5.23%; N: 6.06%; Si: 3.04%; tested value C: 85.69%; H: 5.24%; N: 6.05%; Si: 3.04%.

Embodiment 3

[0038] Embodiment 3: the synthesis of compound 003

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

[0040]

[0041] Weigh 16.97g of silicon-containing benzanthracene bromine substituent, 65.70g of 2-naphthyltriphenylamine, 12.32g of potassium tert-butoxide, 0.56g of palladium (II) acetate, and 0.51g of tri-tert-butylphosphine, and use 250ml of toluene was dissolved and reacted at 85°C for 7 hours. 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 46.84 g of yellow-white solid compound 003 with a yield of more than 91% and an HPLC purity of more than 98%. Mass spectrum: Calculated value is 1029.35; found value is 1029.37. Elemental analysis: calculated value C: 86.35%; H: 5.48%; N: 5.44%; Si: 2.73%; tested value C: 86.36%; H: 5.47%; N: 5.45%; Si: 2.72%.

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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 problems that the anthracene luminescent material in the prior art can not satisfy the operating requirement for OLEDs (organic light-emitting diodes). The 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 different substituted groups, the material has the advantages of higher solubility and favorable film-forming properties. The preparation method provided by the invention has the advantages of simple synthesis and purification processes and low cost, and can satisfy the demands of industrialization. Compared with the device prepared by using 9,10-di(2-naphthyl)anthracene as the luminescent layer, the device prepared from the material provided by the invention has obviously higher luminescence efficiency and longer half-time service life; the luminescence efficiency is 25 Lm / w, and the half-time service life is 20000 hours; and thus, the material can satisfy the operating requirements for OLEDs.

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] Compared with the existing liquid crystal and plasma flat panel display technology, organic electroluminescent display technology has many advantages such as simple structure, active light emission, high brightness, high efficiency, large viewing angle, fast response speed, and low-voltage DC drive. Organic light-emitting diode (OLED), as a new generation of flat panel display technology, has great market potential and competitiveness. In OLED research, materials play a decisive role. The materials used in OLED mainly include hole injection materials, hole transport materials, luminescent materials, electron transport materials and electron injection materials. The luminescent material is one of the main materials. Many...

Claims

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Application Information

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IPC IPC(8): C07F7/10C09K11/06H01L51/54
Inventor 马晓宇王辉李文军
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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