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Imidazole compound and applications thereof

A general formula compound, unsubstituted technology, applied in the direction of organic chemistry, chemical instruments and methods, electrical components, etc., can solve the problems of unreported applications, stability needs to be improved, low triplet energy level, etc., to reduce conjugation degree, improve device efficiency and life, and reduce the effect of implantation energy barrier

Pending Publication Date: 2020-03-13
BEIJING ETERNAL MATERIAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since benzimidazole is substituted by alkyl, its stability needs to be improved
In addition, in this patent, most of the benzimidazoles are connected to the condensed ring, the energy level of the triplet state is low, and the application of this series of compounds as the main body of TADF has not been reported.

Method used

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  • Imidazole compound and applications thereof
  • Imidazole compound and applications thereof
  • Imidazole compound and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0053] Synthesis Example 1: Synthesis of M1

[0054]

[0055] Synthesis of intermediate M1-1:

[0056] 12.2g (100mmol) of o-hydroxybenzaldehyde and 18.4g (100mmol) of o-bromobenzaldehyde were added to a newly dried 1000mL two-necked bottle, and 20.7g (150mmol) of anhydrous potassium carbonate and 600mL of dried potassium carbonate were added under nitrogen protection. N,N-dimethylformamide (DMF), stirred at room temperature for 5 hours, then heated to 130 degrees Celsius to continue the reaction for 10 hours. After the reaction was completed, it was lowered to room temperature, and the solvent in the reaction system was distilled off under reduced pressure. The crude product was dissolved in 500 mL of dichloromethane and washed with a large amount of water. The organic phase was dried over anhydrous sodium sulfate and then concentrated. Column chromatography was performed with dichloromethane:petroleum ether=1:1 as the eluent to obtain 20 g of off-white solid with a yield ...

Synthetic example 2

[0059] Synthesis Example 2: Synthesis of M2

[0060]

[0061] Synthesis of intermediate M2-1:

[0062] 12.2g (100mmol) o-hydroxybenzaldehyde and 32.1g (100mmol) 9-(2-bromophenyl)-9H-carbazole were added to a freshly dried 1000mL two-necked bottle, and 20.7g ( 150 mmol) of anhydrous potassium carbonate and 600 mL of dry N,N-dimethylformamide (DMF), stirred at room temperature for 5 hours, then heated to 130 degrees Celsius to continue the reaction for 10 hours. After the reaction was completed, it was lowered to room temperature, and the solvent in the reaction system was distilled off under reduced pressure. The crude product was dissolved in 500 mL of dichloromethane and washed with a large amount of water. The organic phase was dried over anhydrous sodium sulfate and then concentrated. Column chromatography was performed with dichloromethane:petroleum ether=1:3 as the eluent to obtain 35 g of off-white solid with a yield of 96%. The molecular mass determined by mass spe...

Synthetic example 3

[0065] Synthesis Example 3: Synthesis of M46

[0066]

[0067] Synthesis of Intermediate M46-1:

[0068] Add 32.4g (100mmol) of 4,6-dibromodibenzothiophene and 112.8g (300mmol) of 2-formylphenylboronic acid into a freshly dried 3000mL two-necked bottle, and add 62.1g (450mmol) under nitrogen protection Anhydrous potassium carbonate, 6.9 g (6 mmol) palladium tetrakistriphenylphosphine and 225 mL water and 1500 mL 1,4-dioxane. After the reaction was completed, it was lowered to room temperature, and the solvent in the reaction system was distilled off under reduced pressure. The crude product was dissolved in 500 mL of dichloromethane and washed with a large amount of water. The organic phase was dried with anhydrous sodium sulfate and then concentrated. Column chromatography was performed with dichloromethane:petroleum ether=1:1 as the eluent to obtain 30 g of off-white solid with a yield of 80%. The molecular mass determined by mass spectrometry is: 376.05 (calculated val...

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PUM

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Abstract

The invention discloses a compound represented by a general formula (1), wherein Z is S or O, X<1>-X<10> are respectively and independently selected from CR<3> and N, X<9> and X<10> can be connected by a single bond or not, R<1> and R<2> are respectively and independently selected from one of hydrogen, C1-C12 alkyl, C6-C30 aryl and C3-C30 heteroaryl, R<3> is selected from hydrogen, C1-C12 alkyl, C6-C30 aryl and C3-C30 heteroaryl, L<1> and L<2> are respectively and independently selected from one of a single bond, C6-C30 aryl and C3-C30 heteroaryl, Ar<1> is selected from substituted or unsubstituted imidazole groups, and Ar<2> is selected from one of C6-C30 aryl and C3-C30 heteroaryl. When the compound is used as a luminescent material in an OLED device or an electron transport material, the compound shows excellent device performance and stability. The invention also discloses an organic light-emitting device adopting the compound represented by the general formula.

Description

technical field [0001] The invention relates to an imidazole organic compound, which can be used as a host material or electron transport material of an organic electroluminescent device; the invention also relates to the application of the compound in an organic electroluminescent device. Background technique [0002] Organic light-emitting diodes (OLEDs) have many advantages such as self-luminescence, wide viewing angle, low power consumption, and high contrast, so they have a wide range of applications in white lighting, flexible displays, ultra-thin displays, and transparent displays. [0003] Since the Chinese scientist Professor Deng Qingyun discovered OLEDs in 1987, organic electroluminescent materials have undergone thirty years of development. The first-generation luminescent materials are fluorescent materials, which can only use 25% of singlet excitons to emit light, and the luminous efficiency is low, which directly leads to high power consumption of OLEDs. Phos...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/18C07D403/12C07D471/04C07D405/14C07D401/14C07D405/04C07D403/14C07D409/14C07D491/048C07D495/04C07D409/04C09K11/06H01L51/50H01L51/54
CPCC07D235/18C07D403/12C07D471/04C07D405/14C07D401/14C07D405/04C07D403/14C07D409/14C07D491/048C07D495/04C07D409/04C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1044C09K2211/1088C09K2211/1092H10K85/615H10K85/626H10K85/654H10K85/6576H10K85/6572H10K85/6574H10K50/11H10K50/16
Inventor 魏金贝李国孟高文正孙磊
Owner BEIJING ETERNAL MATERIAL TECH
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