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A kind of organic electroluminescent material and its application

An electroluminescent material and electroluminescent device technology, which can be used in organic chemistry, circuits, electrical components, etc., to solve problems such as low quantum efficiency and achieve good efficiency.

Active Publication Date: 2017-11-24
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In existing reports, the most common central structure of blue light-emitting devices is anthracene, followed by closed-ring organic molecules such as fluorene and pyrene. Among pyrene molecules, pyrene is a rigid condensed ring structure with good thermal stability. properties, but the quantum efficiency is relatively low

Method used

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  • A kind of organic electroluminescent material and its application
  • A kind of organic electroluminescent material and its application
  • A kind of organic electroluminescent material and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Embodiment 1: the preparation of intermediate 2

[0048]

[0049] Preparation of intermediate 1: Add 1,6-dibromopyridine (7.16g, 0.02mol) and cuprous cyanide (CuCN) (5.34g, 0.06mol) into 300g N,N-dimethyl In methyl formamide (DMF), under nitrogen protection, start stirring and reflux condensed water, set the bath temperature to 150°C, heat up to reflux, and reflux for 10 hours. TLC detects that the reaction of 1,6-dibromopyridine is complete, and cools down to room temperature for 25 ℃. Suction filtration under reduced pressure, and the filtrate was directly passed through a silica gel column. 300g of water was added to the column liquid, solids were precipitated, and the crude product was obtained by suction filtration under reduced pressure. The obtained crude product was purified by silica gel column chromatography, and the eluent was n-hexane:dichloroethane=3:1 (V / V), to obtain Intermediate 1, gray solid 4.0g, yield 80%, MS (m / s): 253.1.

[0050]Preparation of...

Embodiment 2

[0051] Embodiment 2: the preparation of intermediate 5

[0052]

[0053] Preparation of Intermediate 3: Add 1,6-dibromopyridine (17.9 g, 0.05 mol) and 536.8 g THF into a 1 L three-necked flask, and stir to dissolve at room temperature at 25°C. The temperature was lowered to below -70°C, and 2.5 mol / l n-BuLi (44 mL, 0.11 mol) was slowly added dropwise. After stirring for 1 hour, N,N-dimethylformamide (9.7 g, 0.132 mol) was added dropwise, and the addition was completed within 30 minutes. The temperature was slowly raised to room temperature 25° C., stirred for 2.0 hours, and 200 ml of saturated ammonium chloride aqueous solution was added to quench the reaction. Separate the liquid and remove the solvent under reduced pressure. Recrystallization was carried out using toluene and absolute ethanol to obtain intermediate 3, weighing 7.2 g, yield: 56%, MS (m / s): 258.2.

[0054] Preparation of Intermediate 4: Add Intermediate 3 (5.16 g, 0.02 mol) into a 500 mL three-neck flask...

Embodiment 3

[0056] Embodiment 3: the preparation of compound C01

[0057]

[0058] In a 250mL three-necked flask, add intermediate 2 (4.08g, 0.01mol) prepared in Example 1, carbazole (3.7g, 0.022mol), catalyst Pd(OAc) 2 (23mg, 0.1mmol), ligand 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl (S-phos) (84mg, 0.2mmol), sodium tert-butoxide (3.84g, 0.04mol) , toluene (150mL), N 2 Protect, stir, heat up to reflux, react for 8-10 hours, turn off the heating, and cool down to room temperature 25°C. 150 mL of deionized water was washed once, separated, the organic phase was collected, and the solvent was removed. The obtained crude product was purified by silica gel column chromatography, and the eluent was n-hexane:dichloroethane=4:1 (V / V), and the target Object C01, crude product weight 4.7g, use toluene and absolute ethanol to recrystallize, obtain 3.5g target object C01, yield 60%.

[0059] High resolution mass spectrometry, ESI source, molecular formula C 42 h 22 N 4 , the theoretic...

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Abstract

The invention relates to an organic electroluminescent material and its application. The organic electroluminescent material takes a pyrene ring as the center, introduces a substituent containing a carbazole group into the 1 and 6 positions of the pyrene ring, and introduces a substituent containing a cyano group into the pyrene ring. The substituents of the group are introduced into the 3 and 8 positions of the pyrene ring. Carbazole is an electron-rich group with good hole transport ability. As a strong electron-withdrawing group, the cyano group can promote intramolecular charge transfer and make the molecular dipole moment Biasing can greatly improve the performance of the material. Pyrene is a rigid condensed ring structure with good thermal stability. The above excellent properties make the organic electroluminescent material have good film stability and exciton transport ability, and can be used as a blue light emitting material in the field of organic electroluminescence.

Description

technical field [0001] The invention relates to an organic electroluminescent material and its application, belonging to the field of organic electroluminescent materials. Background technique [0002] Organic electroluminescent device (OLED), as a new generation of flat panel display technology, has gradually entered people's field of vision. It is a promising new type of flat panel display. It has become one of the hottest topics in the field of flat panel display information display and scientific research product development. [0003] After years of development, monochrome devices have reached the level of practicality, and the light-emitting wavelength of organic electroluminescent materials has covered the entire visible light range. OLEDs are widely used in national defense, households and various digital devices, such as: MP3 player As one of the scientific and technological standards of a country in the information age, OLEDs such as mobile phones, digital cameras,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/82C07D209/86C07D209/80C07D209/94H01L51/54
Inventor 李庆董鹏超张学衡盛磊石宇赵文渊
Owner VALIANT CO LTD