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Organic electroluminescent material and preparation method thereof

An electroluminescent material and luminescence technology, applied in the direction of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems that the luminous efficiency of luminescent materials cannot meet the requirements of OLEDs, etc., and achieve improved luminous efficiency, high purity, and synthesis and purify simple effects

Active Publication Date: 2015-05-20
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to solve the technical problem that the luminous efficiency of existing luminescent materials still cannot meet the requirements of OLEDs, the present invention provides a benzoacridine-based organic electroluminescent material with high luminous efficiency and a preparation method thereof

Method used

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  • Organic electroluminescent material and preparation method thereof
  • Organic electroluminescent material and preparation method thereof
  • Organic electroluminescent material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: the synthesis of compound 001

[0028] Concrete synthetic route is as follows:

[0029]

[0030] Weigh 21.72g of 7H-benzoacridine, 42.47g of 2-bromopyrene, 13.46g of potassium tert-butoxide, 0.41g of palladium (II) acetate, and 0.45g of tri-tert-butylphosphine, and dissolve them in 250ml of toluene, under nitrogen protection , reacted at 80°C for 10 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 35.48 g of yellow-white solid compound 001 with a yield of more than 85% and an HPLC purity of more than 98%. Mass Spectrum: Calculated 417.50; Found 417.52. Elemental analysis: calculated value C: 92.06%; H: 4.59%; N: 3.35%; tested value C: 92.07%; H: 4.60%; N: 3.33%.

Embodiment 2

[0031] Embodiment 2: the synthesis of compound 002

[0032] Concrete synthetic route is as follows:

[0033]

[0034] Weigh 21.72g of 7H-benzoacridine, 51.87g of 4-bromotriphenylamine, 14.36g of potassium tert-butoxide, 0.48g of palladium (II) acetate, and 0.54g of tri-tert-butylphosphine, dissolve in 250ml of toluene, and store at 82°C React for 11 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 39.15 g of yellow-white solid compound 002 with a yield of more than 85% and an HPLC purity of more than 98%. Mass Spectrum: Calculated 460.57; Found 460.56. Elemental analysis: calculated value C: 88.67%; H: 5.25%; N: 6.08%; tested value C: 88.69%; H: 5.24%; N: 6.07%.

Embodiment 3

[0035] Embodiment 3: the synthesis of compound 003

[0036] Concrete synthetic route is as follows:

[0037]

[0038] Weigh 21.72g of 7H-benzoacridine, 43.71g of 2-bromoanthracene, 15.26g of potassium tert-butoxide, 0.56g of palladium (II) acetate, and 0.63g of tri-tert-butylphosphine, dissolve in 250ml of toluene, and react at 84°C 12 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 33.84 g of yellow-white solid compound 003 with a yield of more than 86% and an HPLC purity of more than 98%. Mass spectrum: calculated value 397.51; found value 397.52. Elemental analysis: calculated value C: 90.64%; H: 5.83%; N: 3.52%; tested value C: 90.62%; H: 5.84%; N: 3.53%.

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Abstract

The invention relates to an organic electroluminescent material and a preparation method thereof, and solves the technical problem that the luminous efficiency of the conventional luminescent material cannot meet requirements of an OLED (Organic Light Emitting Diode). The organic electroluminescent material is a novel material which is synthesized by introducing C14-C20 condensed ring aryl group, triarylated amine or N-phenyl-3-carbazolyl based on 7H-benzacridine. Compared with 7H-benzacridine, the synthesized green organic electroluminescent material has a bigger plane structure and a conjugated system, and can change electron transition energy level, thereby changing luminescent spectrum and obviously improving luminous efficiency. The preparation method of the organic electroluminescent material is simple in synthesis and purification, low in cost, and can meet requirements of industrial development.

Description

technical field [0001] The invention relates to the field of organic photoelectric materials, in particular to a benzoacridine-based organic electroluminescence material and a preparation method thereof. Background technique [0002] Organic electroluminescence refers to the phenomenon that organic materials are excited by electric current and electric field to emit light 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. [0003] In OLED research, the choice of organic materials plays a decisive role. The organic materials used in OLED mainly include hole injection materials, hole transport materials, luminescent materials,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/18C07D401/04C09K11/06
Inventor 马晓宇李文军李明彭勃
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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