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 problems that the luminous efficiency of luminescent materials cannot meet the requirements of OLEDs, etc., and achieve improved luminous efficiency, high purity, and good Effects of planar structures and conjugated systems

Active Publication Date: 2014-03-05
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 bisbenzoacridine 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

[0026] Embodiment 1: the synthesis of compound 001

[0027] Concrete synthetic route is as follows:

[0028]

[0029] Weigh 35.79g of 1,6-dibromopyrene, 64.18g of 7H-benzoacridine, 13.46g of potassium tert-butoxide, 0.41g of palladium (II) acetate, and 0.45g of tri-tert-butylphosphine, dissolve them in 250ml of toluene, and Under the protection of nitrogen, react at 80°C for 10 hours. Filter the reaction solution, purify the obtained crude product with silica gel chromatography, then recrystallize the obtained solid crude product with toluene, and dry to obtain 53.78g yellow-white solid bisbenzoacridine compound 001, with a yield of more than 85%, HPLC The purity is greater than 98%. Mass spectrum: calculated value 632.75; found value 632.73. Elemental analysis: calculated value C: 91.11%; H: 4.46%; N: 4.43%; tested value C: 91.13%; H: 4.47%; N: 4.40%.

Embodiment 2

[0030] Embodiment 2: the synthesis of compound 002

[0031] Concrete synthetic route is as follows:

[0032]

[0033] Weigh 35.20 g of 2,7-dibromo-9,9-dimethylfluorene, 67.35 g of 7H-benzoacridine, 14.36 g of potassium tert-butoxide, 0.48 g of palladium (II) acetate, and 0.54 g of tri-tert-butylphosphine g, dissolved in 250ml of toluene, and reacted at 82°C for 11 hours. Filter the reaction solution, purify the obtained crude product with silica gel chromatography, recrystallize the obtained solid crude product with toluene, and dry to obtain 51.85g of yellow-white solid bisbenzoacridine compound 002, with a yield of more than 83% and HPLC purity Greater than 98%. Mass Spectrum: Calculated 624.77; Found 624.75. Elemental analysis: calculated value C: 90.35%; H: 5.16%; N: 4.48%; tested value C: 90.34%; H: 5.18%; N: 4.47%.

Embodiment 3

[0034] Embodiment 3: the synthesis of compound 003

[0035] Concrete synthetic route is as follows:

[0036]

[0037] Weigh 33.60g of 9,10-dibromoanthracene, 69.52g of 7H-benzoacridine, 15.26g of potassium tert-butoxide, 0.56g of palladium(II) acetate, and 0.63g of tri-tert-butylphosphine, dissolve them in 250ml of toluene, and React at 84°C for 12 hours. Filter the reaction solution, purify the obtained crude product with silica gel chromatography, recrystallize the obtained solid crude product with toluene, and dry to obtain 52.35g of yellow-white solid bisbenzoacridine compound 003, with a yield of more than 86%, HPLC purity Greater than 98%. Mass Spectrum: Calcd. 608.73; Tested 608.71. Elemental analysis: calculated value C: 90.76%; H: 4.64%; N: 4.60%; tested value C: 90.77%; H: 4.63%; N: 4.59%.

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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 7H-benzacridine as a basis and introducing a polycyclic aromatic group on the basis. Compared with 7H-benzacridine, the organic electroluminescent material provided by the invention has a better plane structure and conjugated system and can adjust the luminescent peak by adjusting electron transition to obtain the needed green organic electroluminescent material. The luminescent efficiency of the organic electroluminescent material is obviously improved. The preparation method of the organic electroluminescent material, which is provided by the invention, is relatively simple in synthesis and purification 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 bisbenzoacridine-based organic electroluminescence material and a preparation method thereof. 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. 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, electron transport materials and electron injection materials, among which luminescent materials are the main materials. Many research institutions and enterprises at home and abroad have done a lot of research work to continuously improve t...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D221/18C07D401/14
Inventor 马晓宇李贺陈明李文军
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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