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Arylamine compounds containing arylpyridine groups and application of arylamine compounds containing arylpyridine group

A compound and aromatic group technology, applied in the field of aromatic amine compounds, can solve the problems of low luminous efficiency, great difference in luminous efficiency, and the requirements for conjugated body and molecular weight should not be too large, so as to achieve high efficiency and low Effect of driving voltage, high electron and hole mobility

Active Publication Date: 2014-02-26
TSINGHUA UNIV +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is worth noting that most host materials still use FIrpic as a dye to realize blue phosphorescent devices, and the luminous efficiency of FIrpic blue phosphorescent devices with different host materials varies greatly.
Moreover, the blue phosphorescent main body requires a high triplet energy level, so the conjugated body degree and molecular weight requirements of this type of material should not be too large, and materials that meet such requirements often cannot meet the requirements of materials with high Tg (glass transition temperature). ) to obtain blue phosphorescent devices with high efficiency and high stability and long life
Therefore, in the current white light lighting scheme, the blue light part still uses blue fluorescent light with low luminous efficiency.

Method used

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  • Arylamine compounds containing arylpyridine groups and application of arylamine compounds containing arylpyridine group
  • Arylamine compounds containing arylpyridine groups and application of arylamine compounds containing arylpyridine group
  • Arylamine compounds containing arylpyridine groups and application of arylamine compounds containing arylpyridine group

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Experimental program
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Effect test

Embodiment 1

[0049] The synthesis of embodiment 1 phenylpyridylboronic acid and pyridylphenylboronic acid

[0050] (1) Synthesis of 2-bromo-6-phenylpyridine (M11) and 6-phenylpyridine-2 boronic acid (M12)

[0051]

[0052] 25.85g 2,6-dibromopyridine, 13.20g phenylboronic acid and 0.55g Pd(PPh 3 ) 4 Dissolve in a mixture of 330mL toluene and 220mL ethanol, dissolve 24.2g potassium carbonate in 110mL water and add to the above reaction solution, stir and react at 50°C for 1.5h, then add 2.75g phenylboronic acid, react for another 0.5h, monitor by TLC end point of the reaction. After the reaction was completed, the organic phase was separated, washed three times with water and washed with anhydrous Na 2 SO 4 Carry out column chromatography after drying, eluent is sherwood oil: methylene chloride=20: 1 (V 1 / V 2 ), to obtain 15.60 g of white solid. MS (m / e): 234, yield 61%.

[0053]

[0054] Dissolve 15.6g of 2-bromo-6-phenylpyridine and 16.4g of triisopropyl borate in 1400mL of ...

Embodiment 3

[0104] The synthesis of embodiment 3 compound P9

[0105]

[0106] 4,4',4"-tribromotriphenylamine (4.8, 10 mmol), 2-phenylpyridine-5-boronic acid (9.1 g, 39 mmol), palladium chloride (0.35 g, 2 mmol), triphenylphosphine ( 1.05g, 4mmol), anhydrous potassium carbonate (16.5g, 120mmol), 150ml of toluene, 150ml of ethanol, and 60ml of water were added to a 500ml three-necked flask, and magnetically stirred and heated to reflux under nitrogen protection for 24h. Cooling, liquid separation, and rotary evaporation Solvent, eluted with 1 / 8 ethyl acetate + petroleum ether (v / v) and separated by column chromatography to obtain 4.8 grams of white solid, yield: 68%. Product MS (m / e): 704, corresponding to: C 51 h 36 N 4 =704.86, proving that the compound is P9. The synthesis of embodiment 4 compound P21

Embodiment 4

[0106] 4,4',4"-tribromotriphenylamine (4.8, 10 mmol), 2-phenylpyridine-5-boronic acid (9.1 g, 39 mmol), palladium chloride (0.35 g, 2 mmol), triphenylphosphine ( 1.05g, 4mmol), anhydrous potassium carbonate (16.5g, 120mmol), 150ml of toluene, 150ml of ethanol, and 60ml of water were added to a 500ml three-necked flask, and magnetically stirred and heated to reflux under nitrogen protection for 24h. Cooling, liquid separation, and rotary evaporation Solvent, eluted with 1 / 8 ethyl acetate + petroleum ether (v / v) and separated by column chromatography to obtain 4.8 grams of white solid, yield: 68%. Product MS (m / e): 704, corresponding to: C 51 h 36 N 4 =704.86, proving that the compound is P9. The synthesis of embodiment 4 compound P21

[0107]

[0108] The synthesis method is the same as that of P9, except that the raw materials 4,4',4"-tribromotriphenylamine and 2-phenylpyridine-5-boronic acid are replaced by the aforementioned intermediate N-biphenyl-4,4'-di Bromodiphen...

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Abstract

The invention relates to compounds with the general formula (1) shown in the specifications. Ar1, Ar2 and Ar3 are substituent groups, wherein at least one group is an aromatic group which contains a pyridine ring and has 5 to 60 carbon atoms, and the residual groups are independently selected from hydrogen atoms, alkane with 1 to 40 carbon atoms, an aromatic group with 5 to 50 carbon atoms and a nitrogen-containing heterocycle with 5 to 50 carbon atoms; and n in the aromatic group is 1 or 2. The invention also provides application of the compounds to organic electroluminescent devices, particularly use of the compounds as matrix materials of phosphorescent dopants in electrophosphorescent devices or electron transport materials.

Description

technical field [0001] The invention relates to an aromatic amine compound and its application in the technical field of organic electroluminescence display. Background technique [0002] Organic electroluminescence (hereinafter referred to as OLED) and corresponding research began as early as the 1960s. In 1963, p.pope and others 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 made an amorphous film device by vapor-depositing Alq3 and HTM-2, which reduced the driving voltage to less than 20V, and OLED attracted the attention of the world (US4356429). Due to the advantages of high brightness, wide viewing angle, fast photoelectric response, low voltage, low power consumption, rich colors, high contrast, light and thin structure, an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/38H01L51/54H01L51/50
Inventor 邱勇李银奎李建仁乔娟段炼
Owner TSINGHUA UNIV