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2, 2-dimethyl-1, 3-indandione derivatives and organic electroluminescence device based on same

A technology of indanedione and dimethyl, applied in the field of organic electroluminescence devices

Active Publication Date: 2016-06-22
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no report on the application of 1,3-indanedione as an electron acceptor fragment in OLED devices

Method used

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  • 2, 2-dimethyl-1, 3-indandione derivatives and organic electroluminescence device based on same
  • 2, 2-dimethyl-1, 3-indandione derivatives and organic electroluminescence device based on same
  • 2, 2-dimethyl-1, 3-indandione derivatives and organic electroluminescence device based on same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] Reaction is as shown in (formula 8):

[0078]

[0079] The specific steps of the reaction are as follows:

[0080] Under argon protection, 252 mg of 5-bromo-2,2-dimethyl-1,3-indanedione, 680 mg of 9,9-dimethylacridine, 15 mg of palladium acetate, 1.1 g of potassium tert-butoxide, 0.3 mL of a toluene solution of tri-tert-butylphosphine with a volume fraction of 10% and 10 mL of toluene to obtain the first mixed solution; the first mixed solution was heated to 90° C. and stirred under reflux After 48 hours, the second mixed solution was obtained; the second mixed solution was cooled to room temperature, and the organic solvent was distilled off to obtain the third mixed solution; a large amount of water and dichloromethane were added to the third mixed solution for extraction, and the extracted The final organic phase was dried with anhydrous sodium sulfate, filtered, and then the organic liquid phase was distilled off to obtain a crude product; the crude product was ...

Embodiment 2

[0084] Reaction is as shown in (formula 9):

[0085]

[0086] The specific steps of the reaction are as follows:

[0087] S01: Slowly add 4.7g (0.21mol) of sodium into 50mL (0.48mol) of absolute ethanol to make sodium ethylate; add the sodium ethylate to 60mL of methyl propionate and 52.8g (0.15mol) of 5, In the mixed solution of 6-dibromophthalic acid dimethyl ester, the temperature was raised to 80°C and stirred for 4 hours to obtain a light yellow viscous paste; then the methanol in the paste was distilled to , ethanol, and methyl propionate were removed, then suction filtered, the filter residue was washed with petroleum ether, and 40.5 g of a light yellow solid was obtained after vacuum drying.

[0088] S02: Add the light yellow solid to 100 mL of 3 mol / L hydrochloric acid solution, then raise the temperature to 90°C and stir until CO is generated 2 Cool until it is removed, then suction filter after cooling to obtain light yellow crystals, wash the light yellow crys...

Embodiment 3

[0095] Reaction is as shown in (formula 10):

[0096]

[0097] The specific steps of the reaction are as follows:

[0098] S1: Under argon protection, add 350 mg of 5,6-dibromo-2,2-dimethyl-1,3-indandione, 680 mg of phenoxazine, and acetic acid into a 100 mL reactor equipped with a reflux tube 15 mg of palladium, 1.1 g of potassium tert-butoxide, 0.3 mL of a toluene solution of tri-tert-butylphosphine with a volume fraction of 10%, and 10 mL of toluene to obtain the first mixed solution; the first mixed solution was heated to 90° C. and stirred under reflux After 48 hours, the second mixed solution was obtained; the second mixed solution was cooled to room temperature, and the organic solvent was distilled off to obtain the third mixed solution; a large amount of water and dichloromethane were added to the third mixed solution for extraction, and the extracted The final organic phase is dried and filtered with anhydrous sodium sulfate, and then the organic liquid phase is ...

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Abstract

The invention provides a 5-substituted 2, 2-dimethyl-1, 3-indandione derivative and a 5, 6-substituted 2, 2-dimethyl-1, 3-indandione derivative; the structural formulas of the two derivatives are described in the description, wherein R, R1 and R2 respectively represent an electron-rich aromatic amine substituent group containing at least one nitrogen, amino nitrogen is connected with 2, 2-dimethyl-1, 3-indandione, or R2 represents a substituted aromatic hydrocarbyl; the invention also provides a preparation method of the 5-substituted 2, 2-dimethyl-1, 3-indandione derivative and a preparation method of the 5, 6-substituted 2, 2-dimethyl-1, 3-indandione derivative; an organic electroluminescence device which takes an organic thin film layer formed by the 5-substituted 2, 2-dimethyl-1, 3-indandione derivative or the 5, 6-substituted 2, 2-dimethyl-1, 3-indandione derivative as a luminescent layer has the advantages of being driven by low voltage, being high in efficiency, stable in luminescence and long in service life, and the like.

Description

technical field [0001] The invention relates to 2,2-dimethyl-1,3-indanedione derivatives and an organic electroluminescent device based on the same, belonging to the field of organic electroluminescent devices. Background technique [0002] An organic electroluminescence (OLED) device is a light-emitting layer containing a light-emitting material sandwiched between an electron-transporting layer and a hole-transporting layer, and a cathode and an anode are further installed outside it, and electrons and holes are injected into the device by an external voltage. And recombine in the light-emitting layer to form a device in which the excitons emit photons and deactivate through the process of fluorescence or phosphorescence. Because of its full solid state, self-illumination, wide viewing angle, fast response, low driving voltage, low energy consumption and many other characteristics, it has great application prospects in the field of flat panel display and solid light source....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D219/02C07D265/38C07C49/697C07C45/68C09K11/06H01L51/54
CPCC09K11/06C07C45/673C07C45/68C07C49/697C07C67/313C07D219/02C09K2211/1029C09K2211/1011C09K2211/1033H10K85/657H10K85/6572H10K50/11C07C69/757
Inventor 张晓宏陈冬阳郑才俊
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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