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Metatriazine-like compound, electronic device and application

A metatriazine-like compound technology is applied in the field of organic optoelectronic materials to achieve the effects of easy availability of raw materials, enhanced durability, and broad industrialization prospects

Inactive Publication Date: 2020-10-30
SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Overall, the future direction of organic electroluminescent devices is to develop high-efficiency, long-life, low-cost white light devices and full-color display devices, but the industrialization process of this technology still faces many key problems

Method used

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  • Metatriazine-like compound, electronic device and application
  • Metatriazine-like compound, electronic device and application
  • Metatriazine-like compound, electronic device and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0120] Embodiment 1: the synthesis of compound 8-5

[0121] (Synthesis of intermediate M1)

[0122] The synthetic route of intermediate M1 is as follows:

[0123]

[0124] P-bromobenzohydrazide (4.3g, 20mmol), ninhydrin (3.6g, 20mmol), ammonium acetate (12.0g, 90mmol) and 120mL acetic acid were successively added into a 250mL single-necked flask, and the reaction was stirred under reflux for 12 hours. After the reaction was complete, the solid was collected by suction filtration and washed with a small amount of absolute ethanol. The crude product was further purified by column chromatography (petroleum ether:dichloromethane=3:1 (V / V)). The solvent was evaporated, and after drying, 3.9 g of a light yellow solid was obtained, with a yield of 58%. MS (EI): m / z: 336.58 [M + ]. Anal.calcdforC 16 h 8 BrN 3 O (%): C 56.83, H 2.38, N 12.43; found: C 56.75, H 2.35, N 12.40.

[0125] (Synthesis of Intermediate M2)

[0126] The synthetic route of intermediate M2 is as follo...

Embodiment 2

[0134] Embodiment 2: the synthesis of compound 9-5

[0135] (Synthesis of compound 9-5)

[0136] The synthetic route of compound 9-5 is as follows:

[0137]

[0138] Under the protection of nitrogen, 2.9 g (8.9 mmol) of 2-bromotriphenylamine and 150 mL of anhydrous tetrahydrofuran were added to a dry and clean 250 mL three-necked flask, and stirred and dissolved at room temperature. The system was cooled to -78°C, and 3.9 mL (2.5 M, 9.8 mmol) of n-butyllithium was added dropwise at this temperature, and stirring was continued at this temperature for 1.5 h after the addition was complete. Subsequently, 4.4 g (8.1 mmol) of intermediate M2 was added in one batch, and the cooling bath was removed after the addition, and the reaction was warmed to room temperature by itself and continued to stir overnight. After the reaction, it was washed with water, dried, and spin-dried to obtain a white solid.

[0139] The above white solid was transferred to a 250mL one-necked bottle equ...

Embodiment 3

[0140] Embodiment 3: the synthesis of compound 7-5

[0141] (Synthesis of compound M3)

[0142] The synthetic route of compound M3 is as follows:

[0143]

[0144] In a 250mL three-neck flask equipped with a reflux condenser and a dropping funnel, add 1g (5.9mmol) iodine element and 100mL glacial acetic acid under nitrogen protection, stir and dissolve, then add about 3.9g (29.6mmol) hypophosphorous acid, and heat up to React at 120°C until the color of the system fades. Then add 11.4g (14.8mmol) M2 at one time, continue to heat and reflux for 4h, cool to room temperature, pour into water to precipitate a large amount of white solid, filter, wash and dry to obtain 6.4g of white crystalline solid, yield 82%. MS (EI): m / z: 526.48 [M + ]. Anal.calcd for C 37 h 24 N 2 (%): C 84.38, H 4.98, N 10.64; found: C 84.30, H 4.95, N 10.63.

[0145] (Synthesis of compound 7-5)

[0146] The synthetic route of compound 7-5 is as follows:

[0147]

[0148] Transfer 7.3g (13.9mm...

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Abstract

The invention relates to a metatriazine-like compound, an electronic device and application. According to the metatriazine-like compound disclosed by the invention, a metatriazine-like rigid structureis introduced, so that the obtained metatriazine-like compound is excellent in membrane-forming property and thermal stability, and can be used for preparing an organic light-emitting device, an organic field effect transistor and an organic solar cell. In addition, the metatriazine-like compound can be used as a constituent material of a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, a hole blocking layer or an electron transport layer, and can reduce the driving voltage, improve the efficiency, improve the brightness, prolong the service life and the like. Besides, the preparation method of the metatriazine-like compound is simple, raw materials are easy to obtain, and industrial development requirements can be met.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and relates to a partial triazine compound, an electronic device containing the partial triazine compound, and an application thereof. More specifically, the present invention relates to partial triazine compounds suitable for electronic devices, especially organic electroluminescent devices, organic field effect transistors and organic solar cells, and electronic devices using the partial triazine compounds. Background technique [0002] Organic electroluminescent devices have a series of advantages such as self-luminescence, low-voltage drive, full curing, wide viewing angle, simple composition and process, etc. Compared with liquid crystal displays, organic electroluminescent devices do not need a backlight. Therefore, organic electroluminescent devices have broad application prospects. [0003] An organic electroluminescent device generally includes an anode, a metal ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D253/10C07D403/10C07D471/04C07D487/10C07D471/10C07D491/048C07D519/00C07D495/04C07D487/04C07D403/14C09K11/06H01L51/50H01L51/54H01L51/42H01L51/05
CPCC07D253/10C07D403/10C07D471/04C07D487/10C07D471/10C07D491/048C07D519/00C07D495/04C07D487/04C07D403/14C09K11/06C09K2211/1029C09K2211/1044C09K2211/1059C09K2211/1074C09K2211/1062C09K2211/1066H10K85/631H10K85/6572H10K85/657H10K10/46H10K30/00H10K50/11H10K50/18H10K50/16H10K50/17H10K50/15Y02E10/549
Inventor 张业欣朱向东刘向阳崔林松陈华
Owner SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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