A kind of high-efficiency organic light-emitting material and its preparation and application

An electroluminescent material and organic technology, applied in the direction of luminescent materials, preparation of organic compounds, organic chemistry, etc., can solve the problems of complex synthesis methods, low brightness, low efficiency, and inability to fully satisfy full-color display, and achieve high luminescence efficiency effect

Active Publication Date: 2017-01-18
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Compared with green organic electroluminescent devices, blue organic electroluminescent devices cannot fully meet the requirements of full-color display
At present, blue-light organic light-emitting materials are mainly concentrated in some classic compound systems such as triarylamine systems, anthracene derivatives, carbazole derivatives, and metal complexes. However, these existing blue-light organic light-emitting materials are still facing difficulties in application, such as The life, brightness, and efficiency are low, which cannot meet the needs of industrialization; moreover, the synthesis methods of these materials are complicated, the purification is difficult, and relatively toxic raw materials are used in the synthesis process

Method used

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  • A kind of high-efficiency organic light-emitting material and its preparation and application
  • A kind of high-efficiency organic light-emitting material and its preparation and application
  • A kind of high-efficiency organic light-emitting material and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: the synthesis of compound 001

[0024] The specific synthetic route is shown in the following formula:

[0025]

[0026] (1) Weigh 37.8g of tetrabenzotriphenyl, dissolve it in 200mL of dichloromethane, add 39.16g of NBS, raise the temperature to 40°C, stir and react for 24 hours, spin dry the organic solvent, and put the obtained crude product into the column layer Analysis (petroleum ether / dichloromethane=1:1) resulted in 41.83 g of light yellow solid 6,13-dibromotetrabenzotriphenyl.

[0027] (2) Under the condition of nitrogen protection, add 30ml of anhydrous tetrahydrofuran solution, 3.74g of magnesium bars, and 2 pieces of iodine into the three-necked flask. After the Grignard reagent triggers, add 41.83g of 6,13-dibromotetrabenzotriphenyl 100ml of anhydrous tetrahydrofuran solution, reacted for 3 hours under ice-water bath conditions, added dropwise 12ml of anhydrous N,N-dimethylformamide to the reaction solution, then slowly raised to room tempe...

Embodiment 2

[0030] Embodiment 2: the synthesis of compound 002

[0031] The specific synthetic route is shown in the following formula:

[0032]

[0033] (1) Weigh 37.8g of tetrabenzotriphenyl, dissolve it in 200mL of dichloromethane, add 39.16g of NBS, raise the temperature to 40°C, stir and react for 24 hours, spin dry the organic solvent, and put the obtained crude product into the column layer Analysis (petroleum ether / dichloromethane=1:1) resulted in 41.83 g of light yellow solid 6,13-dibromotetrabenzotriphenyl.

[0034] (2) Under the condition of nitrogen protection, add 30ml of anhydrous tetrahydrofuran solution, 3.74g of magnesium bars, and 2 pieces of iodine into the three-necked flask. After the Grignard reagent triggers, add 41.83g of 6,13-dibromotetrabenzotriphenyl 100ml of anhydrous tetrahydrofuran solution, reacted for 3 hours under ice-water bath conditions, added dropwise 12ml of anhydrous N,N-dimethylformamide to the reaction solution, then slowly raised to room tempe...

Embodiment 3

[0037] Embodiment 3: the synthesis of compound 003

[0038] The specific synthetic route is shown in the following formula:

[0039]

[0040] (1) Weigh 37.8g of tetrabenzotriphenyl, dissolve it in 200mL of dichloromethane, add 39.16g of NBS, raise the temperature to 40°C, stir and react for 24 hours, spin dry the organic solvent, and put the obtained crude product into the column layer Analysis (petroleum ether / dichloromethane=1:1) resulted in 41.83 g of light yellow solid 6,13-dibromotetrabenzotriphenyl.

[0041] (2) Under the condition of nitrogen protection, add 30ml of anhydrous tetrahydrofuran solution, 3.74g of magnesium bars, and 2 pieces of iodine into the three-necked flask. After the Grignard reagent triggers, add 41.83g of 6,13-dibromotetrabenzotriphenyl 100ml of anhydrous tetrahydrofuran solution, reacted for 3 hours under ice-water bath conditions, added dropwise 12ml of anhydrous N,N-dimethylformamide to the reaction solution, then slowly raised to room tempe...

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PUM

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Abstract

The tetrabenzotriphenylene organic light-emitting materials involved in the present invention can be used in the structure of organic electroluminescent devices. The series of derivatives are based on tetrabenzotriphenyl compounds, and are obtained by The introduction of olefins, continued introduction of aromatic amines, substituted or unsubstituted condensed ring aryl groups, substituted or unsubstituted aromatic heterocyclic groups and other substituent groups can adjust electronic transitions and meet the needs of light-emitting materials. High luminous efficiency, the luminous efficiency in the dilute solution is about 96%, and the luminous efficiency in the film can reach about 63%, indicating that the tetrabenzotriphenylene compound has high luminous efficiency. Compared with tetrabenzotriphenyl, the preparation method of the tetrabenzotriphenyl organic electroluminescent material provided by the present invention has relatively simple synthesis and purification, low cost, and can meet the needs of industrialization development. The yield of the product is greatly improved, and the purity is high, and the HPLC purity is greater than 98%. Moreover, the prepared material can significantly improve the efficiency, and have obvious improvements in film-forming performance and service life.

Description

technical field [0001] The invention belongs to the field of organic photoelectric materials, and in particular relates to a tetrabenzotriphenylene organic luminescent material and a preparation method and application thereof. Background technique [0002] Organic electroluminescence (hereinafter referred to as OLED) and corresponding research began as early as the 1960s. In 1963, Pope et al. first discovered the electroluminescence phenomenon of organic single crystal anthracene, but due to the limitation of technical conditions, its driving voltage was as high as 400V, which failed to attract widespread attention. In 1987, C.W.Tang et al. of Kodak Corporation of the United States used evaporation Alq 3 An amorphous film device was made with HTM-2, and the driving voltage was reduced to less than 20v, so OLED attracted the attention of the world (US4356429). This type of device can be widely used in planar light-emitting components such as flat panel displays and panels d...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07C15/56C07C13/62C07C1/32C07D209/86C07D215/06C07D277/66C07C211/58C07C209/10
Inventor 马晓宇李贺彭勃
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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