Pyrimidoindole derivative and organic light-emitting diode device thereof

A technology of indole derivatives and pyrimidines, which is applied in the field of pyrimidoindole derivatives and their organic electroluminescence devices, to achieve the effects of improving physical properties, easily obtaining raw materials, and improving luminous efficiency

Inactive Publication Date: 2018-03-20
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there is no stable and efficient luminescent host material yet, so the continuous research and development of new host materials is still necessary

Method used

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  • Pyrimidoindole derivative and organic light-emitting diode device thereof
  • Pyrimidoindole derivative and organic light-emitting diode device thereof
  • Pyrimidoindole derivative and organic light-emitting diode device thereof

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preparation example Construction

[0042] The preparation method of the pyrimidoindole derivatives of the present invention, the specific synthetic route is as follows:

[0043]

[0044] Using 9-bromo-10-nitrophenanthrene as raw material, react to generate intermediate (BH); intermediate (BH) undergoes Suzuki reaction with 4-bromo-2,6-dichloropyrimidine to obtain intermediate (A); intermediate Body (A) produces ring-forming reaction, obtains intermediate (B); Intermediate (B) and containing R 1 The bromide reaction of group generates intermediate (C); Intermediate (C) and containing R 2 The boronic acid pinacol ester compound of group reacts, generates intermediate (D); Finally, intermediate (D) and containing R 3 The boric acid pinacol ester compound of the group reacts to synthesize the target compound (I).

[0045] The present invention has no special limitation on the reaction conditions of the above-mentioned reactions, and the reaction conditions well-known to those skilled in the art can be adopted....

Embodiment 1

[0050] Embodiment 1: the preparation of intermediate (BH)

[0051] Under an argon atmosphere, 400 ml of dehydrated tetrahydrofuran was added to 30.21 g (100 mmol) of 9-bromo-10-nitrophenanthrene, and cooled to -40°C. Slowly add 63ml of 1.6M n-butyllithium hexane solution, heat to 0°C, stir for 1 hour, then cool to -78°C, add dropwise 50ml of dehydrated tetrahydrofuran solution containing 26.0g (250mmol) trimethyl borate , stirred at room temperature for 5 hours. 200 ml of 1N hydrochloric acid was added dropwise, and after stirring for 1 hour, the aqueous layer was removed. The organic layer was dried with anhydrous magnesium sulfate, the organic solvent was distilled off under reduced pressure, and washed with toluene to obtain 18.43 g (69 mmol) of intermediate (BH) with a yield of 69%.

Embodiment 2

[0052] Embodiment 2: the preparation of intermediate (A)

[0053] 13.35g (50mmol) intermediate (BH), 11.39g (50mmol) 4-bromo-2,6-dichloropyrimidine, 1.73g (1.5mmol) tetrakis (triphenylphosphine) palladium, 6g (150mmol) hydroxide Sodium was dissolved in a mixed solution of 250ml of anhydrous tetrahydrofuran and 125ml of water, and the reaction was refluxed for 24 hours. After the reaction, the system was cooled to room temperature, extracted with dichloromethane, and washed with water. It was 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 16.29 g (44 mmol) of Intermediate (A), with a yield of 88%.

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Abstract

The invention provides a pyrimidoindole derivative and an organic light-emitting diode (OLED) device thereof, and relates to the technical field of organic photoelectric materials. According to the pyrimidoindole derivative provided by the invention, indole and pyrimidine are connected in parallel; on the basis, a phenanthrene structure is formed by connecting two benzene rings and a benzene ringof the indole in parallel, so that the structure has relatively strong stability; the structure is used as a parent nucleus structure, and physical performance of the structure is further improved through changing a radical connected with the structure, so that a series of pyrimidoindole derivatives are obtained. The compound is a main body material with good performance, a preparation method is simple, and raw materials are easy to obtain; when the pyrimidoindole derivative is applied to the OLED device, the light-emitting efficiency of the device can be improved, the driving voltage is reduced, 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 pyrimidoindole derivative and an organic electroluminescence device thereof. Background technique [0002] In recent years, with the increasing demand for flat panel displays, organic electroluminescent devices (OLEDs) have attracted more and more attention from scientists. Compared with thin-film transistor-liquid crystal display (TFT-LCD), OLED has the advantages of lower driving voltage, smaller shape, wider viewing angle, faster response time, etc., and can provide equivalent or better image quality, especially for small And medium size, and the manufacturing process is simple, which is more competitive with other types of display devices. [0003] Organic materials used in OLED devices are called organic electroluminescent materials (OLED materials), which are divided into hole injection materials, hole transport materials, electron blocking materi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C07D519/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D487/04C07D519/00C09K2211/1044C09K2211/1011C09K2211/1007C09K2211/1029C09K2211/1092C09K2211/1088H10K85/622H10K85/615H10K85/6576H10K85/6574H10K85/6572H10K50/11H10K2102/00H10K2102/301
Inventor 周雯庭蔡辉
Owner CHANGCHUN HYPERIONS TECH CO LTD
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