Novel aromatic amine compound and preparation and application thereof

A technology of aromatic amines and compounds, applied in the field of new aromatic amine compounds and their preparation and application, which can solve the problems of general material performance and achieve the effects of long life, high brightness and high efficiency

Active Publication Date: 2015-12-30
SHANGHAI SHINSEE OPTOELECTRONICS TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The characteristics of the currently required materials are that the substance has thermal stability and fast electron mo

Method used

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  • Novel aromatic amine compound and preparation and application thereof
  • Novel aromatic amine compound and preparation and application thereof
  • Novel aromatic amine compound and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0084] Example: Synthesis of Intermediate

[0085] Synthesis of the intermediate 2-chloro-6-phenylpyridine (1-1)

[0086]

[0087] Synthesis method: 2-bromo-6-chloropyridine (21.2g, 0.11mol), phenylboronic acid (12.2g, 0.10mol), 0.5g tetrakistriphenylphosphorus palladium, add to a 1000ML reaction flask, add 400ML toluene, carbonic acid The sodium aqueous solution (2N, 150 mL) was protected by nitrogen and reacted in an oil bath at 80°C for 24 hours. Post-treatment process: cool down, stand still for 30 minutes to separate liquids, save the organic layer, spin dry toluene, add methylene chloride to the solid to dissolve, pass through the column for separation, PE:DCM=1:1, get A-1(9.6g, y=51%)

[0088] Synthesis of intermediates 1-2 and 1-3

[0089] According to the above-mentioned synthesis method of Intermediate 1-1, the following compounds are obtained:

[0090]

[0091] Synthesis of intermediate 6-chloro-N,N-diphenylpyridine-2-amine (1-4):

[0092]

[0093] Synthesis method: add dip...

Example Embodiment

[0125] Example 5 Synthesis of 10-diphenylpyrido[3,2-g]quinoline(6-1)

[0126]

[0127] Add the prepared 5,10-dichloro-pyrido[g]quinoline 5-1 (14.8g, 0.6mmol), 4-boronic acid pyridine (18g, 0.146mmol), and 4g of tetratriphenylphosphine palladium into the reaction flask Add toluene, ethanol and water 2:1:1 (volume ratio) mixed solution totaling 600mL, nitrogen protection, stirring and heating to 110°C for 24 hours. Post-treatment process: cooling system, liquid separation, spin-dry toluene. Add dichloromethane to dissolve the solid, pass the column, and wash with petroleum ether: ethyl acetate=2:1 (volume ratio) to obtain a solid (6-1) (13g, y=65%).

Example

[0128] Synthesis of Examples 6-2~6-17

[0129] According to the synthesis method of Example 6-1 above, the compounds in the following table were obtained:

[0130]

[0131]

[0132]

[0133]

[0134] Example N5, N5, N10, N10-Tetraphenylpyrido[3,2-g]quinoline-5,10-diamine (6-23) synthesis:

[0135]

[0136] According to the synthesis method of Intermediate 1-4, 5,10-dichloropyrido[3,2-g]quinoline (6.0g, 24mmol) and diphenylamine (4.4, 24mmol) were used as raw materials for the reaction to obtain N5, N5, N10, N10-tetraphenylpyrido[3,2-g]quinoline-5,10-diamine (6.17g, y=50%).

[0137] Example 5 Synthesis of 10-bis(1-naphthyloxy)pyrido[3,2-g]quinoline (6-24):

[0138]

[0139] Dissolve 1-hydroxynaphthalene (14g, 0.1mol) in 100mL of anhydrous tetrahydrofuran, stir, accurately weigh NaH (0.96g, 0.4mol) and add them to the reaction flask in batches, not too fast to prevent too many bubbles. After the addition, the solution turned yellow, and then 5,10-dichloropyrido[3,2-g]quinoline (27.50g, ...

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Abstract

The invention discloses a novel aromatic amine compound. The compound molecule general formula of the novel aromatic amine compound can be seen in the specification, wherein R1, R2 and R3 are alkyl with the hydrogen atom number or carbon atom number ranging from 1 to 30 or aryl with the carbon atom number ranging from 6 to 50 or heterocyclic radicals with the carbon atom number ranging from 5 to 50 or aromatic amidogen with the carbon atom number ranging from 6 to 30, Ar1 and Ar2 are aklary with hydrogen atom number or the carbon atom number ranging from 7 to 50 or aryloxy with the carbon atom number ranging from 7-50 or alkaryl sulfydryl with the carbon atom number ranging from 7 to 50 or aryl with the carbon atom number ranging from 6 to 50 or heterocyclic radicals with the carbon atom number ranging from 5 to 50 or aromatic amine with the carbon atom number ranging from 6 to 30 or aryloxy with the carbon atom number ranging from 6-50 or aryloxy aryl sulfydryl with the carbon atom number ranging from 6-50. The aromatic heterocyclic compound is used for preparing organic electro-devices, and the devices manufactured through the novel heterocyclic compound have the advantages of being high in brightness, good in heat resistance, long in service life, high in efficiency and the like.

Description

Technical field [0001] The invention relates to the field of electroluminescent materials, in particular to a new aromatic amine compound and its preparation and application. Background technique [0002] The host materials in electroluminescent devices mainly include small molecule host materials and polymer host materials. Many high-efficiency electroluminescent devices have been prepared using small-molecule host materials doped with phosphorescent complexes as light-emitting layers. In recent years, the use of polymer host materials doped with various phosphorescent complex guests as the light-emitting layer to prepare electroluminescent devices has received more attention. Due to the rapid development of optoelectronic communication and multimedia fields in recent years, organic optoelectronic materials have become the core of modern society's information and electronic industries. [0003] Organic electroluminescence device (OLED) is a new type of flat display device. Compa...

Claims

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Application Information

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IPC IPC(8): C07D471/04C09K11/06H01L51/54
CPCC09K11/06C07D471/04C09K2211/1092C09K2211/1007C09K2211/1011C09K2211/1029H10K85/653H10K85/655H10K85/631H10K85/636H10K85/626H10K85/654H10K85/6572Y02E10/549
Inventor 高春吉王士凯张成成王贺崔敦洙
Owner SHANGHAI SHINSEE OPTOELECTRONICS TECH CO LTD
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