Imidazole substituted spirofluorene compound and applications thereof

A general formula compound, unsubstituted technology, applied in the field of imidazole-substituted spirofluorene organic compounds, organic electroluminescent devices, can solve the problems of weak electron transport ability and unbalanced carrier transport

Active Publication Date: 2020-01-31
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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  • Imidazole substituted spirofluorene compound and applications thereof
  • Imidazole substituted spirofluorene compound and applications thereof
  • Imidazole substituted spirofluorene compound and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 2

[0068] Synthesis Example 2: Synthesis of M2:

Synthetic example 3

[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. Synthesis Example 3: Synthesis of M12:

[0070] 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 press...

Synthetic example 4

[0071] Synthesis Example 4: Synthesis of M46:

[0072] According to the synthesis of M12, the steps are the same, and 3-cyanophenylboronic acid is used instead of 3-boronic acid-9-phenylcarbazole for reaction to obtain 8.23 ​​g of off-white solid with a yield of 90%. The molecular ion mass determined by mass spectrometry is: 457.14 (calculated value: 457.16); theoretical element content (%) C 33 h 19 N 3 : C, 86.63; H, 4.19; N, 9.18. Measured element content (%): C, 86.64; H, 4.17; N, 9.20. The above analysis results showed that the obtained product was the expected product.

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Abstract

The invention discloses an imidazole substituted spirofluorene compound and applications thereof, and discloses a compound represented by the following general formula defined in the specification, wherein X<1>-X<4> are selected from CR4 or N, R<4> is selected from hydrogen, C1-C10 alkyl, substituted or unsubstituted C6-C15 aryl and substituted or unsubstituted C3-C15 heteroaryl, R<1>-R<3> are selected from hydrogen, C1-C10 alkyl, substituted or unsubstituted C6-C15 aryl and substituted or unsubstituted C3-C15 heteroaryl, R<1>-R<3> are respectively and independently fused to a linked benzene ring to form C9-C30 aryl or heteroaryl, m and n are integers of 0-4, p is an integer of 0-3, L<1> and L<2> are selected from single bonds, substituted or unsubstituted C6-C30 arylene and substituted orunsubstituted C3-C30 heteroarylene, and Ar<1> and Ar<2> are selected from hydrogen, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl. According to the invention, with the application of the imidazole substituted spirofluorene compound as the luminescent material in an OLED device or an electron transport material, the compound shows excellent device performance and excellent stability. The invention further discloses an organic light-emitting device adopting the compound with the 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 Applications(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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