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Organic electroluminescent material and preparation method thereof

An electroluminescent material and luminescent technology, applied in the direction of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problem that the luminous efficiency of luminescent materials cannot meet the requirements of OLEDs, etc., and achieve improved luminous efficiency, easy materials, and low cost. cheap effect

Active Publication Date: 2014-11-05
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In order to solve the technical problem that the luminous efficiency of the existing luminescent materials still cannot meet the requirements of OLEDs, the present invention provides a kind of benzoacridine olefins with high luminous efficiency, an organic electroluminescent material 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 69.38g of 3-methyl-7H-benzoacridine, 124.24g of 2-bromonaphthalene, 40.38g of potassium tert-butoxide, 1.23g of palladium (II) acetate, and 1.35g of tri-tert-butylphosphine, and dissolve them in 250ml of toluene , and reacted at 80° C. for 10 hours under the protection of nitrogen. The reaction solution was filtered, and the obtained crude product was purified by silica gel chromatography, and then the obtained solid crude product was recrystallized with toluene and dried to obtain 3-methyl-7-(2-naphthyl)-7H-benzoacridine 91.14 g, 85% yield.

[0031] Add 26.60g MnO to 91.14g of 3-methyl-7-(2-naphthyl)-7H-benzoacridine 2 , 65% H 2 SO 4 10ml was dissolved in 250ml of toluene and reacted for 12 hours to obtain 89.47g of 7-(2-naphthyl)-7H-benzoacridine-3-carbaldehyde with a yield of 95%.

[0032]Under the condition of nitrogen protection, add 38.06g ...

Embodiment 2

[0033] Embodiment 2: the synthesis of compound 002

[0034] Concrete synthetic route is as follows:

[0035]

[0036] Weigh 69.38g of 3-methyl-7H-benzoacridine, 124.24g of 2-bromonaphthalene, 40.38g of potassium tert-butoxide, 1.23g of palladium (II) acetate, and 1.35g of tri-tert-butylphosphine, and dissolve them in 250ml of toluene , and reacted at 80° C. for 10 hours under the protection of nitrogen. The reaction solution was filtered, and the obtained crude product was purified by silica gel chromatography, and then the obtained solid crude product was recrystallized with toluene and dried to obtain 3-methyl-7-(2-naphthyl)-7H-benzoacridine 91.14 g, 85% yield.

[0037] Add 26.60g MnO to 91.14g of 3-methyl-7-(2-naphthyl)-7H-benzoacridine 2 , 65% H 2 SO 4 10ml was dissolved in 250ml of toluene and reacted for 12 hours to obtain 89.47g of 7-(2-naphthyl)-7H-benzoacridine-3-carbaldehyde with a yield of 95%.

[0038] Under the condition of nitrogen protection, add 40.39g...

Embodiment 3

[0039] Embodiment 3: the synthesis of compound 003

[0040] Concrete synthetic route is as follows:

[0041]

[0042] Weigh 69.38g of 3-methyl-7H-benzoacridine, 124.24g of 2-bromonaphthalene, 40.38g of potassium tert-butoxide, 1.23g of palladium (II) acetate, and 1.35g of tri-tert-butylphosphine, and dissolve them in 250ml of toluene , and reacted at 80° C. for 10 hours under the protection of nitrogen. The reaction solution was filtered, and the obtained crude product was purified by silica gel chromatography, and then the obtained solid crude product was recrystallized with toluene and dried to obtain 3-methyl-7-(2-naphthyl)-7H-benzoacridine 91.14 g, 85% yield.

[0043] Add 26.60g MnO to 91.14g of 3-methyl-7-(2-naphthyl)-7H-benzoacridine 2 , 65% H 2 SO 4 10ml was dissolved in 250ml of toluene and reacted for 12 hours to obtain 89.47g of 7-(2-naphthyl)-7H-benzoacridine-3-carbaldehyde with a yield of 95%.

[0044] Under the condition of nitrogen protection, add 43.06g...

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Abstract

The invention relates to an organic electroluminescent material and a preparation method thereof, solving the technical problem that the luminescent efficiency of existing luminescent materials still can not meet the requirements of an OLED (organic light emitting diode). The novel organic electroluminescent material is synthesized by using 3-methyl-7H-benzacridine as a basis and introducing one of phenyl, p-methylphenyl and p-methoxyphenyl as well as a C10-C16 polycyclic aromatic hydrocarbon substituent group. Compared with 3-methyl-7H-benzacridine, the synthesized green organic electroluminescent material has a larger plane structure and conjugated system and can change the electron transition energy level, thus changing the luminescent spectrum, improving the luminescent efficiency and being capable of meeting the requirements of the OLED. The preparation method of the organic electroluminescent material, which is provided by the invention, is relatively simple in synthesis and purification, easy in purification of materials and low in cost, and can meet the requirements of industrialization development.

Description

technical field [0001] The invention relates to the field of organic photoelectric materials, in particular to a benzoacridine olefin-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. In OLED research, the choice of luminescent material plays a decisive role. Many research institutions and enterprises at home and abroad have done a lot of research work to continuously improve the comprehensive performance of luminescent materials, and have achieved rich research results. However, the luminous efficiency of current luminescent materials still cannot meet the requirements of OLEDs. [0003] Acridine compounds are mac...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/18C09K11/06
Inventor 马晓宇王辉李国强李文军
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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