Benzimidazole compound and derivatives, organic electronic transmission material as well as preparation of benzimidazole compound and derivatives and application of organic electronic transmission material

A technology of benzimidazole and transport materials, which is applied in the materials of organic semiconductor devices, organic chemistry, organic light-emitting devices, etc., to achieve the effect of enhancing rigid structure, enhancing rigidity, and enhancing long-term stability

Inactive Publication Date: 2018-04-20
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, a large number of small organic molecule electron transport materials have been reported, but the synthesis and purification challenges of organic small molecule electron transport materials with excellent comprehensive properties are common

Method used

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  • Benzimidazole compound and derivatives, organic electronic transmission material as well as preparation of benzimidazole compound and derivatives and application of organic electronic transmission material
  • Benzimidazole compound and derivatives, organic electronic transmission material as well as preparation of benzimidazole compound and derivatives and application of organic electronic transmission material
  • Benzimidazole compound and derivatives, organic electronic transmission material as well as preparation of benzimidazole compound and derivatives and application of organic electronic transmission material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Embodiment 1 benzimidazole compound

[0053] A benzimidazole compound (2-(6-bromonaphthalene-2-yl)-1-phenyl-1H-benzimidazole), its structure is as follows:

[0054]

[0055] The preparation method of described benzimidazole compound comprises the following steps:

[0056] S1: Preparation of 6-bromo-2-naphthoyl chloride (1), the reaction equation is as follows:

[0057]

[0058] Under ice bath conditions, 6-bromo-2-naphthoic acid (5.0g, 19.91mmol) and thionyl chloride (14.2g, 119.48mmol) were added to a certain amount of chloroform (30ml), and the reaction was stirred at 60°C for 14 After ~16 hours, after the reaction was completed, chloroform was distilled off under reduced pressure to obtain 6-bromo-2-naphthoyl chloride (compound 1) as a white solid.

[0059] S2: Preparation of 6-bromo-N-(2-(phenylamino)phenyl)-2-naphthylcarboxamide (2), the reaction equation is as follows:

[0060]

[0061] 6-Bromo-2-naphthoyl chloride (compound 1) (5.36g, 19.91mmol) and o...

Embodiment 2

[0066] Example 2: Organic Electron Transport Materials

[0067] An organic small molecule electron transport material (PBI-Na-Phen) with high thermal stability and thin film morphology stability is a benzimidazole compound derivative with the following structure:

[0068]

[0069] The preparation method of described organic small molecule electron transport material (PBI-Na-Phen), comprises the following steps:

[0070] T1: 1-phenyl-2-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)- The preparation of 1H-benzimidazole (4), reaction equation is as follows:

[0071]

[0072] 2-(6-bromonaphthalene-2-yl)-1-phenyl-1H-benzimidazole (compound 3) (3.0g, 7.51mmol) and biborpinacol ester (2.86g, 11.27mmol) and potassium acetate (2.21g, 22.53mmol) were added in a certain amount of tetrahydrofuran (60ml), under N 2 Under the atmosphere, add bistriphenylphosphine palladium dichloride (158mg, 0.225mmol), and stir the reaction at 80°C for 3-4 hours. After the reacti...

Embodiment 3

[0086] Embodiment 3 organic electron transport material

[0087] An organic small molecule electron transport material (PBI-Na-Trz) with high thermal stability and thin film morphology stability is a benzimidazole compound derivative with the following structure:

[0088]

[0089] The preparation method of described organic small molecule electron transport material (PBI-Na-Trz), comprises the following steps:

[0090] (1) 1-phenyl-2-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene-2-yl) -1H-benzimidazole (compound 4): this step is the same as in Example 2;

[0091] (2) 2-(6-(4,6-diphenyl-1,3,5-triazin-2-yl)naphthalene-2-yl)-1-phenyl-1H-benzimidazole (PBI- Na-Trz) preparation, reaction equation is as follows:

[0092]

[0093] Compound 4 (1.4g, 3.15mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (0.90g, 3.36mmol) were dissolved in toluene (50ml), and an appropriate amount of ethanol ( 6ml) and potassium carbonate aqueous solution (2M, 4ml, 8mmol), in N 2 U...

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Abstract

The invention belongs to the technical field of an organic photoelectric functional molecular material and discloses a benzimidazole compound and derivatives, an organic electronic transmission material as well as preparation of the benzimidazole compound and derivatives and application of the organic electronic transmission material. The organic electronic transmission material comprises at leastone of benzimidazole compound derivatives. The structure of the benzimidazole compound derivatives is as shown in a formula II or a formula III. The method comprises the following steps: (a) in a catalytic system, performing Suzuki reaction of the benzimidazole compound and double pinacol diborane and performing subsequent treatment to obtain a product containing boric acid ester; (b) in the catalytic system, performing coupling reaction of the product containing boric acid ester and 3-bromine-1,10-phenanthroline or 2-chlorine-4,6-diphenyl-1,3,5-triazine and performing subsequent treatment toobtain the benzimidazole compound derivatives. The organic electronic transmission material has high heat stability and film appearance stability and is favorable for improving the stability of devices; and the synthesis method is simple and easy in purification. (The formula is as shown in the description).

Description

technical field [0001] The present invention relates to small organic molecule functional materials, especially electron transport materials, in particular to a benzimidazole compound and its derivatives, an organic electron transport material and its preparation method and application. The organic electron transport material includes at least one kind of benzimidazole compound derivatives. Background technique [0002] Organic light-emitting diodes (OLEDs) have important applications in novel electroluminescent displays and lighting. Among them, the high-performance organic molecular electron transport material is the key functional material of OLED, which assists the injection of electrons from the cathode to the light-emitting layer. Amorphous organic electron transport materials with high thermal stability and thin film morphology stability are crucial for obtaining highly stable organic light-emitting diodes. [0003] The design of electron transport materials require...

Claims

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Application Information

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IPC IPC(8): C07D235/18C07D471/04C07D403/10H01L51/50H01L51/54
CPCC07D235/18C07D403/10C07D471/04H10K85/615H10K85/654H10K85/6572H10K50/16H10K2102/00H10K2102/301
Inventor 朱旭辉陈玲玲彭俊彪曹镛
Owner SOUTH CHINA UNIV OF TECH
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