A kind of imidazole substituted spirofluorene compound and application thereof

A general formula compound, unsubstituted technology, applied in the field of organic electroluminescent devices, imidazole substituted spirofluorene organic compounds, can solve the problems of weak electron transport ability, unbalanced carrier transport, etc., to achieve lower injection energy barrier, Effect of reducing efficiency roll-off and reducing turn-on voltage

Active Publication Date: 2022-05-20
BEIJING ETERNAL MATERIAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The purpose of the present invention is to solve the problems of weak electron transport ability and unbalanced carrier transport in the above-mentioned prior art, to propose a novel general formula compound with good electron transport ability, and to provide an effective compound using this novel compound. Electromechanical Luminescent Devices

Method used

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  • A kind of imidazole substituted spirofluorene compound and application thereof
  • A kind of imidazole substituted spirofluorene compound and application thereof
  • A kind of imidazole substituted spirofluorene compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0060] Synthesis Example 1: Synthesis of M1

[0061]

[0062] Synthesis of intermediate M1-1:

[0063] Add 11.8g (100mmol) of benzimidazole and 20.2g of 2-fluoro-4-bromobenzaldehyde (100mmol) into a freshly dried 500mL two-necked bottle, and add 20.7g (150mmol) of anhydrous potassium carbonate under nitrogen protection and 200 mL of dimethylsulfoxide (DMSO). The temperature was raised to 120°C and the reaction was continued for 20h. After the reaction was completed, the temperature was lowered to room temperature, and the reaction system was poured into 1 L of ice water stirred. At this time, a large amount of light yellow precipitates were produced. Suction filtration under reduced pressure and repeated washing with distilled water. The crude product was dissolved in dichloromethane, and the eluent was ethyl acetate:dichloromethane=1:10. Column chromatography gave off-white solid, 12.5 g, yield 42%. The molecular ion mass determined by mass spectrometry is: 298.02 (cal...

Synthetic example 2

[0068] Synthesis Example 2: Synthesis of M2:

[0069] According to the synthesis of M1, the steps were the same, and 5-bromo-2-fluorobenzaldehyde was used instead of 2-fluoro-4-bromo-benzaldehyde to obtain 7.2 g of white solid, with a yield of 69%. The molecular ion mass determined by mass spectrometry is: 521.16 (calculated value: 521.19); theoretical element content (%) C 38 h 23 N 3 : C, 87.50; H, 4.44; N, 8.06. Measured element content (%): C, 87.47; H, 4.42; N, 8.06. The above analysis results indicated that the obtained product was the expected product.

Synthetic example 3

[0070] Synthesis Example 3: Synthesis of M12:

[0071] Take a dry 500mL two-necked bottle, add 8.68g (20mmol) M1-2, 7.2g (25mmol) 3-boric acid-9-phenylcarbazole, 4.14g (30mmol) anhydrous potassium carbonate, 230mg (0.2mmol) ) tetrakistriphenylphosphine palladium. After nitrogen replacement three times, 15 mL of distilled water and 250 mL of 1,4-dioxane were added, and heated to reflux for 12 h. After the solvent in the reaction system was distilled under reduced pressure, it was extracted with dichloromethane and washed with a large amount of water. After combining the organic phases, they were concentrated and subjected to column chromatography using dichloromethane: petroleum ether = 1:1 as the eluent to obtain a white solid, 10.3 g, with a yield of 86%. The molecular ion mass determined by mass spectrometry is: 597.20 (calculated value: 597.22); theoretical element content (%) C 44 h 27 N 3 : C, 88.42; H, 4.55; N, 7.03. Measured element content (%): C, 88.46; H, 4.54;...

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Abstract

The invention protects an imidazole substituted spirofluorene compound and its application, and discloses a compound of the following general formula: X 1 ~X 4 from CR 4 or N,R 4 Selected from hydrogen, C1-C10 alkyl, substituted or unsubstituted C6-C15 aryl, substituted or unsubstituted C3-C15 heteroaryl; R 1 ~R 3 Selected from hydrogen, C1-C10 alkyl, substituted or unsubstituted C6-C15 aryl, substituted or unsubstituted C3-C15 heteroaryl; R 1 ~R 3 Each independently fused with the connected benzene ring to form a C9-C30 aryl or heteroaryl; m, n are integers of 0-4, p is an integer of 0-3; L 1 , L 2 Selected from single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene; Ar 1 , Ar 2 Selected from hydrogen, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl. The compounds of the present invention exhibit excellent device performance and stability when used as light-emitting materials in OLED devices or as electron transport materials. The present invention also protects the organic electroluminescent device using the compound of the above general formula.

Description

technical field [0001] The present invention relates to a novel general formula compound, in particular to an imidazole-substituted spirofluorene organic compound, which can be used as a light-emitting layer host material or an electron transport material of an organic electroluminescent device, and the present invention also relates to a method using the compound Organic electroluminescent devices. Background technique [0002] Since Professor Deng Qingyun, a Chinese scientist, first reported the electroluminescence phenomenon of organic compounds, organic light-emitting diodes (OLEDs) have attracted widespread attention due to their many advantages such as self-luminescence, high contrast, and low power consumption. [0003] At present, in the structure of organic electroluminescent devices in the field of display and lighting, blue fluorescent materials are generally used together with red and green phosphorescent materials. The light-emitting layer of common electrolumi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/10C07D519/00C07F9/6561C09K11/06H01L51/54
CPCC07D519/00C07F9/6561C07D487/10C09K11/06C09K2211/1029C09K2211/1011C09K2211/1014C09K2211/1007C09K2211/1088C09K2211/1044C09K2211/1092C09K2211/1074H10K85/624H10K85/622H10K85/615H10K85/626H10K85/654H10K85/657H10K85/6574Y02E10/549
Inventor 魏金贝李国孟高文正邵爽
Owner BEIJING ETERNAL MATERIAL TECH
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