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Heterocyclic compound and organic light emitting device thereby

A technology of organic light-emitting devices and heterocyclic compounds, applied in the field of organic light-emitting devices, can solve problems such as low luminous brightness, high driving voltage, and efficiency to be improved, and achieve high luminous brightness, low switching voltage, and improved luminous characteristics.

Inactive Publication Date: 2017-06-13
CHANGCHUN HYPERIONS TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compared with inorganic light-emitting diodes, organic light-emitting devices have higher driving voltage, lower luminance, and efficiency needs to be improved

Method used

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  • Heterocyclic compound and organic light emitting device thereby
  • Heterocyclic compound and organic light emitting device thereby
  • Heterocyclic compound and organic light emitting device thereby

Examples

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preparation example Construction

[0040] The preparation method of the heterocyclic compound represented by the formula (I) of the present invention first utilizes the reaction of brominated aromatic compound and aromatic amine derivatives to prepare aromatic diamine series compounds. The bromide of the phenothiazine derivative is then prepared, and the phenothiazine-derived diamine compound is prepared through a substitution reaction. Finally, the compound of formula (I) is prepared by the substitution reaction of diamine compound derived from bromofluorene and phenothiazine, and the reaction process is as follows:

[0041]

[0042] The present invention has no special requirements on the reaction conditions of the above-mentioned various reactions, and the conventional conditions of this type of reaction well known to those skilled in the art can be used. The present invention has no special limitation on the sources of the raw materials used in the above-mentioned various reactions, which can be commerci...

Embodiment 1

[0046] Embodiment 1: the synthesis of compound H-1

[0047] 1. Under nitrogen protection, mix 80mmol of 1-bromobenzene, 90mmol of aniline, 3.2mmol of palladium acetate, 100mmol of cesium carbonate and 4.2mmol of BINAP in a reaction flask in proportion, and add 200ml of dioxane to dissolve the reactant. Heated to reflux and reacted for 12 hours. After cooling the reaction solution to room temperature, it was filtered, washed with dichloromethane, and the organic layer was washed twice with 2M hydrochloric acid and then washed with water. After the solvent was evaporated, the product was separated and purified by column chromatography.

[0048]

[0049] 2. Under the protection of nitrogen, add the p-phenylenediamine and phenothiazine derivatives prepared in step 1 to toluene according to the molar ratio of 1:1, and add potassium tert-butylate and palladium acetate as catalysts at the same time, and heat the reactant to 80 °C for 3 hours and then cooled to room temperature. ...

Embodiment 2

[0053] Embodiment 2: the synthesis of compound H-2

[0054] 1. Under the protection of nitrogen, mix 80mmol of 1-bromonaphthalene, 90mmol of aniline, 3.2mmol of palladium acetate, 100mmol of cesium carbonate and 4.2mmol of BINAP in the reaction flask in proportion, and add 200ml of dioxane to dissolve the reactant. Heated to reflux and reacted for 12 hours. After cooling the reaction solution to room temperature, it was filtered, washed with dichloromethane, and the organic layer was washed twice with 2M hydrochloric acid and then washed with water. After the solvent was evaporated, the product was separated and purified by column chromatography.

[0055]

[0056] 2. Under the protection of nitrogen, add the aromatic diamine and phenothiazine derivatives prepared in step 1 to toluene at a molar ratio of 1:1, and at the same time add potassium tert-butylate and palladium acetate as catalysts, and heat the reactant to 80°C After 3 hours of reaction, the temperature was lowe...

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Abstract

The invention provides a heterocyclic compound and an organic light emitting device thereby, and belongs to the technical field of organic photoelectric materials. The heterocyclic compound is characterized in that a fluorene group is added into a structure to obviously improve the hole transportation performance of the material, and a connected group can be changed to further improve the physical characteristics of the material so as to improve the characteristics of luminescence of the organic light emitting device. When the heterocyclic compound provided by the invention is taken as a hole transportation layer to prepare the organic light emitting device, low switching voltage and high light emitting luminescence can be obtained, and the heterocyclic compound is an excellent OLED (Organic Light Emitting Diode) material.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a heterocyclic compound and an organic light-emitting device using the heterocyclic compound. Background technique [0002] The research on the phenomenon of organic electroluminescence began in the 1960s. In 1963, Pope et al. of New York University in the United States first observed electroluminescence on anthracene single crystals, but due to the excessive thickness of the single crystal, the driving voltage was as high as 400V, which lacked practical value. Subsequent studies have reported a series of electroluminescence phenomena of host organic materials containing conjugated structures. Due to device technology problems, the luminous efficiency is not ideal. Until 1987, Tang et al. from Kodak Company reported the use of 8-hydroxyquinoline aluminum and aromatic diamines with hole transport properties to make high-quality thin films and make organic ...

Claims

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Application Information

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IPC IPC(8): C07D279/22C09K11/06H01L51/50H01L51/54
CPCC07D279/22C09K2211/1037H10K85/636H10K85/657H10K50/15H10K2102/00H10K2102/301
Inventor 郭建华
Owner CHANGCHUN HYPERIONS TECH CO LTD
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