Triphenylene derivative and application thereof

A derivative, triphenylene technology, applied in the field of triphenylene derivatives, achieves the effects of easy-to-obtain raw materials, simple preparation methods, and prolonging service life

Inactive Publication Date: 2018-02-23
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Triphenylene derivatives are one of a class of phosphorescent matrix materials with excellent performance, whi...

Method used

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  • Triphenylene derivative and application thereof
  • Triphenylene derivative and application thereof
  • Triphenylene derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1: the preparation of intermediate A

[0039]

[0040] (1) Preparation of Intermediate A-1: ​​Add 210ml of 2M potassium carbonate to 21.21g (105mmol) of 1-bromo-2-nitrobenzene and 42.86g (157.5mmol) of triphenylene-2-boronic acid Aqueous solution, 12.2g (10.5mmol) tetrakis(triphenylphosphine)palladium, 530ml toluene and 265ml ethanol were heated to 80°C and stirred for 12 hours. After cooling to room temperature, it was extracted with ethyl acetate, the organic layer was washed with distilled water, and then dried over anhydrous magnesium sulfate, and the organic solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography to obtain 31.18 g (89.25 mmol) of a solid, namely Intermediate A-1 (yield 85%).

[0041] (2) Preparation of intermediate A-2: replace 1-bromo-2-nitrobenzene with equimolar 1-bromo-3-methyl-2-nitrobenzene, other steps and intermediate A-1 The preparation is the same, and the intermediate ...

Embodiment 2

[0048] Embodiment 2: the preparation of intermediate B

[0049]

[0050] (1) Preparation of Intermediate B-1: Dissolve 34.75g (88mmol) of Intermediate A-1 in 440ml of o-dichlorobenzene, then add 58.2g (220mmol) of triethyl phosphite, heat to 150°C, and react 24 hours. Cooling, suction filtration, and distillation under reduced pressure to remove the solvent, and the resulting residue was purified by column chromatography to obtain 15.08 g (47.5 mmol) of intermediate B-1 with a yield of 54%.

[0051] (2) Preparation of Intermediate B-2: Intermediate A-1 is replaced by an equimolar amount of Intermediate A-2, and other steps are the same as the preparation of Intermediate B-1 to obtain Intermediate B-2 .

[0052] (3) Preparation of intermediate B-3: Intermediate A-1 is replaced by an equimolar amount of intermediate A-3, and other steps are the same as the preparation of intermediate B-1 to obtain intermediate B-3 . .

[0053] (4) Preparation of intermediate B-4: Interme...

Embodiment 3

[0058] Embodiment 3: the preparation of intermediate C

[0059]

[0060]

[0061] (1) Preparation of intermediate C-1: under argon atmosphere, 12.7g (40mmol) intermediate B-1 and 6.28g (40mmol) bromobenzene, 7.69g (80mmol) sodium tert-butoxide were dissolved in 200ml dry toluene 0.18g (0.8mmol) of palladium acetate and 0.16g (0.8mmol) of tri-tert-butylphosphine were added during stirring, heated to 80°C, and reacted for 8 hours. Cool, filter the reaction system through diatomaceous earth / silica gel, distill off the solvent from the filtrate under reduced pressure, recrystallize the resulting residue in toluene, and filter and dry the crude product to obtain 13.7g (34.8mmol) of intermediate C-1 , and the yield was 87%.

[0062] (2) Preparation of intermediate C-2: Bromobenzene was replaced by an equimolar amount of 4-bromoanisole, and other steps were the same as the preparation of intermediate C-1 to obtain intermediate C-2.

[0063] (3) Preparation of intermediate C-3...

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PUM

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Abstract

The invention provides a triphenylene derivative and application thereof, and relates to the technical field of organic photoelectric materials. The compound takes triphenylene as a parent nucleus structure to modify different benzene rings with different benzene and nitrogen heterocyclic rings to further modify hydrogen of amino groups on the heterocyclic rings and hydrogen on the benzene rings with alkyl groups, substituted or non-substituted aryl groups and substituted or non-substituted condensed aryl groups, thereby obtaining a series of triphenylene derivatives. The preparation method issimple, and the raw materials are readily available; the triphenylene derivative is a matrix material with high performance, has hole transport capacity, and can be used as a hole transport materialapplied to an OLED device, so that the luminous efficiency of the device can be improved, and the service life of the device is prolonged.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a triphenylene derivative and its application. Background technique [0002] Compared with thin-film transistor-liquid crystal displays (TFT-LCDs), organic electroluminescent devices (OLEDs) have various advantages, such as lower driving voltage, smaller shape, wider viewing angle, faster response time, etc. At the same time, OLED provides equivalent or better image quality than TFT-LCD, and the manufacturing process is simple, which is more competitive with other types of display devices. In recent years, with the increasing demand for flat panel displays, the application of organic electroluminescent devices (OLEDs) has attracted more and more attention from scientists. OLED devices have similar electrical characteristics to LEDs (light-emitting diodes). When an electric field is applied to OLED devices, holes and electrons are injected from the anode a...

Claims

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Application Information

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IPC IPC(8): C07D487/06C07D519/00H01L51/54
CPCC07D487/06C07D519/00H10K85/622H10K85/624H10K85/626H10K85/615H10K85/6576H10K85/6574H10K85/6572
Inventor 周雯庭蔡辉
Owner CHANGCHUN HYPERIONS TECH CO LTD
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