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 compound preparation, organic chemistry, etc., can solve the problems that anthracene-based luminescent materials cannot meet the requirements of OLED use, meet the needs of industrial development, and increase productivity , The effect of improving luminous efficiency

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

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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 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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Effect test

Embodiment 1

[0032] Embodiment 1: the synthesis of compound 001

[0033] The specific synthetic route is shown in the following formula:

[0034] Weigh 16.16g of benzanthracene bromine substituents, 32.89g of 2-naphthylphenylamine, 12.32g of potassium tert-butoxide, 0.56g of palladium (II) acetate, and 0.51g of tri-tert-butylphosphine, and dissolve them in 250ml of toluene. Under nitrogen protection, react at 85°C for 7 hours. 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 30.55 g of yellow-white solid compound 001 with a yield of more than 90% and a HPLC purity of more than 98%. Mass Spectrum: Calculated 678.86; Found 678.85. Elemental analysis: calculated value C: 90.23%; H: 5.64%; N: 4.13%; test value C: 90.21%; H: 5.65%; N: 4.14%.

Embodiment 2

[0035] Embodiment 2: the synthesis of compound 002

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

[0037]

[0038] Weigh 16.16g of benzanthracene bromine substituent, 53.50g of N-phenyl-2-carbazolylphenylamine, 12.32g of potassium tert-butoxide, 0.56g of palladium(II) acetate, and 0.51g of tri-tert-butylphosphine , dissolved in 250ml of toluene, and reacted at 90°C for 8 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 41.82 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 909.12; Found 909.14. Elemental analysis: calculated value C: 88.52%; H: 5.32%; N: 6.16%; test value C: 88.50%; H: 5.33%; N: 6.17%.

Embodiment 3

[0039] Embodiment 3: the synthesis of compound 003

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

[0041]

[0042] Weigh 16.16g of benzanthracene bromine substituents, 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 dissolve them in 250ml of toluene , reacted at 88°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 47.11 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 value: 1013.27; Tested value: 1013.25. Elemental analysis: the calculated value is C: 88.90%; H: 5.57%; N: 5.53%; the tested value is C: 88.91%; H: 5.58%; N: 5.51%.

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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 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 prepared by reacting R1/R2-substituted amine compound and benzanthracene bromine substitute. Due to the introduction of methyl group in the 10 site, 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 industrialized development. Compared with the device prepared by using arylamino-substituted 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 benzanthracene-based organic electroluminescent material and its preparation method and application. Background technique [0002] Organic electroluminescence (OEL) refers to the phenomenon that organic materials emit light when excited by electric current and electric field under the action of electric field. Organic light-emitting diodes (OLEDs) are a next-generation display technology that utilizes this phenomenon to realize displays. Since Tang C.W. and Vanslyke S.A. of American Kodak Company produced the first organic electroluminescent device with excellent performance in 1987, organic electroluminescent displays have attracted great interest due to their advantages. 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 emis...

Claims

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Application Information

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