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Red electroluminescent compound as well as preparation method and application thereof

A compound and luminescent technology, applied in the field of red electroluminescent compounds and their preparation, can solve the problems of easy crystallization of organic materials, affecting life and efficiency, short service life, etc. The effect of good performance and great application potential

Active Publication Date: 2021-04-27
CHINA PETROLEUM & CHEM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After decades of rapid development, OLED flat panel display technology is becoming mature and has occupied a place in the field of flat panel display, but the current OLED devices are restricted from wider application due to factors such as low efficiency and short service life, especially in Large screen display field
In addition, when the device is operated with an applied voltage, it will generate Joule heat, which makes the organic material easy to crystallize, which affects its life and efficiency to a certain extent.

Method used

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  • Red electroluminescent compound as well as preparation method and application thereof
  • Red electroluminescent compound as well as preparation method and application thereof
  • Red electroluminescent compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] (1) Preparation of compound 1-1

[0049] Under an argon atmosphere, aniline (1.12g, 12mmol), p-bromoxynil (1.81g, 10mmol), palladium acetate (589mg, 0.5mmol), a toluene solution of 1.0M tri-tert-butylphosphine (0.1mL , 1.0mmol), sodium tert-butyl alkoxide (4.80g, 50mmol) was added in 40mL toluene, and reacted at 80°C for 12 hours. After drying, it was purified by silica gel column chromatography, using a mixed solvent of petroleum ether and dichloromethane (volume ratio 2:1) as eluent to obtain a white solid with a yield of 82%. 1 HNMR, 13 CNMR, MS and elemental analysis results show that the obtained compound is the target product 1, and the chemical reaction equation of the preparation process is as follows:

[0050]

[0051] (2) Preparation of compound 1-2

[0052] Under an argon atmosphere, in a 150mL two-necked flask, 4-triphenylamine borate (2.89g, 10mmol) and 1,3,5-tribromobenzene (3.11g, 10mmol) were dissolved in toluene. Palladium Phosphine (Pd(PPh 3 ) ...

Embodiment 2

[0072] Embodiment 2: the preparation of compound RC2

[0073] Under an argon atmosphere, compound 1-6 (20.98g, 25mmol) and compound 3 (4.56g, 10mmol; that is, 4,7-bis(2-bromo-5-thienyl)-2,1,3-benzene Thiadiazole (CAS No.288071-87-4), purchased from Suzhou Aowei Photoelectric New Material Co., Ltd.) was dissolved in toluene, and in the catalyst tetrakistriphenylphosphine palladium (Pd(PPh 3 ) 4 ) (0.58g, 0.5mmol) and a mass fraction of 50% potassium carbonate aqueous solution (6.9g, 50mmol) under the action of a Suzuki coupling reaction, 90 ° C for 24 hours, after the reaction was stopped, the reaction was quenched with water, and dichloro Methane was extracted and dried with anhydrous magnesium sulfate, and then purified by silica gel column chromatography, using a mixed solvent of petroleum ether and dichloromethane (volume ratio 1:1) as eluent to obtain a red solid RC2 with a yield of 74%. 1 HNMR, 13 CNMR, MS and elemental analysis results show that the obtained compound ...

Embodiment 3

[0078] (1) Preparation of compound 3-3

[0079] Under argon atmosphere, compound 1-1 (4.66g, 24mmol), bis(4-tert-butylphenyl)amine (2.81g, 10mmol; CAS No.4627-22-9, purchased from Beijing Huawei Raycus Chemical Co., Ltd. Co., Ltd.), palladium acetate (589mg, 0.5mmol), a toluene solution of tri-tert-butylphosphine (0.1mL, 1.0mmol) at a concentration of 1.0M, and sodium tert-butyl alkoxide (4.80g, 50mmol) were added to 40mL of toluene, React at 80°C for 12 hours. After stopping the reaction, quench the reaction with water, concentrate the solvent, extract with dichloromethane and dry with anhydrous magnesium sulfate, then purify by silica gel column chromatography, petroleum ether and dichloromethane mixed solvent (volume ratio 2:1) is eluent, a white solid was obtained with a yield of 92%. 1 HNMR, 13 The results of CNMR, MS and elemental analysis show that the obtained compound is the target product 3-3, and the chemical reaction equation of the preparation process is as fol...

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Abstract

The invention discloses a red electroluminescent compound as well as a preparation method and application thereof, belonging to the technical field of organic photoelectricity. The red electroluminescent compound has a chemical structural formula shown in the specification. The red electroluminescent compound has the advantages of cheap monomer raw materials, simple synthesis route, convenient purification, convenience in research on a structure-performance relationship, and easiness in industrial scale-up production. The red electroluminescent compound disclosed by the invention is simple in synthetic route, convenient to purify, novel in structure and good in electroluminescent property; the compound has good solubility and can be used for preparing a large-area flexible display device by adopting a solution processing technology; and the compound has huge development potential and prospects in the field of organic electronic display.

Description

technical field [0001] The invention belongs to the technical field of organic optoelectronics, and in particular relates to a red electroluminescent compound and its preparation method and application. Background technique [0002] Organic light-emitting diodes (Organic Light-Emitting Diodes, OLEDs) have unique advantages such as quick response, wide viewing angle, rich colors, light and thin volume, self-luminescence and bendable, rollable and even foldable, and are known as the most potential third Modern display technology has great application prospects in electronic products such as smart phones, TVs, tablet computers, VR (virtual reality, head-mounted display devices) and wearable smart devices. [0003] In OLED devices, the luminescent material determines the preparation method and performance of the device. After decades of rapid development, OLED flat panel display technology is becoming mature and has occupied a place in the field of flat panel display, but the c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06H01L51/54
CPCC07F5/02C09K11/06C09K2211/1014C09K2211/1055C09K2211/1051C09K2211/1092H10K85/631H10K85/655H10K85/657H10K50/11
Inventor 应磊曹镛
Owner CHINA PETROLEUM & CHEM CORP