1,4 di[4-(n,n-p-methylphenyl amido)styryl]naphthyl and method of manufacturing the same and application thereof

A technology based on methylphenylamino and styryl, applied in 1 field, can solve the problems of difficult product purification, air isolation, harsh conditions, etc., and achieve the effects of easy preparation, high electron transfer ability, and mild reaction conditions

Inactive Publication Date: 2008-01-23
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction temperature is high, the conditions are harsh, the air needs to be isolated, and the product is difficult to purify

Method used

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  • 1,4 di[4-(n,n-p-methylphenyl amido)styryl]naphthyl and method of manufacturing the same and application thereof
  • 1,4 di[4-(n,n-p-methylphenyl amido)styryl]naphthyl and method of manufacturing the same and application thereof
  • 1,4 di[4-(n,n-p-methylphenyl amido)styryl]naphthyl and method of manufacturing the same and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Add 12g of 1-chloromethylnaphthalene, 11mL of glacial acetic acid into a 250mL four-neck flask, add 5g of paraformaldehyde, 7mL of phosphoric acid, and 34mL of concentrated hydrochloric acid with a mass fraction of 37% while stirring, reflux at 100°C for 4h, and then cool to 20°C, add diethyl ether to extract, use K 2 CO 3 The saturated solution adjusts the pH to 6-7. Separate the liquid, keep the upper organic liquid, distill the filtrate under reduced pressure at 40 ° C, put it in the refrigerator overnight to precipitate a milky white solid, and recrystallize from ethanol to obtain 3.6 g (yield 28%) of 1,4-dichloromethylnaphthalene as a white needle-like solid , its melting point is 97°C.

[0022] Add 3.6g of 1,4-dichloromethylnaphthalene to a 200mL four-neck flask, reflux 10mL trihexyl phosphite at 180°C for 2h, cool to 20°C, add petroleum ether to precipitate a white solid, filter, and the obtained white Add 60mL of N,N-dimethylformamide (DMF) to the solid, add ...

Embodiment 2

[0026] Add 12g of 1-chloromethylnaphthalene and 11mL of glacial acetic acid into a 250mL four-neck flask, while stirring, add 10g of paraformaldehyde, 7mL of phosphoric acid, and 34mL of concentrated hydrochloric acid with a mass fraction of 37%, react at 80°C for 4h, and then cool to 20°C, add diethyl ether to extract, and use K 2 CO 3 The saturated solution adjusts the pH to 6-7. Separation, retain the upper organic liquid, distill the filtrate under reduced pressure at 40 ° C, put it in the refrigerator overnight to precipitate a milky white solid, recrystallize from ethanol, and obtain 4.6 g (yield 35.8%) of 1,4-dichloromethylnaphthalene as a white needle-like solid , its melting point is 97°C.

[0027] Add 4g of 1,4-dichloromethylnaphthalene to a 200mL four-neck flask, reflux 10mL of trihexyl phosphite at 180°C for 2h, cool to 20°C, add petroleum ether to precipitate a white solid, filter, and the obtained white solid Add 60mL of N,N-dimethylformamide (DMF), add 6g of ...

Embodiment 3

[0031] Add 12g of 1-chloromethylnaphthalene and 11mL of glacial acetic acid into a 250mL four-neck flask, while stirring, add 10g of paraformaldehyde, 7mL of phosphoric acid, and 34mL of concentrated hydrochloric acid with a mass fraction of 37%, reflux at 100°C for 4h, and then cool to 20°C, add petroleum ether for extraction, and use Na 2 CO 3 The saturated solution adjusts the pH to 6-7. Separate the liquid, keep the upper organic liquid, distill the filtrate under reduced pressure at 40 ° C, put it in the refrigerator overnight to precipitate a milky white solid, and recrystallize from ethanol to obtain 3.6 g (yield 28%) of 1,4-dichloromethylnaphthalene as a white needle-like solid , its melting point is 97°C.

[0032] Add 3.6g of 1,4-dichloromethylnaphthalene to a 200mL four-neck flask, reflux 10mL trihexyl phosphite at 180°C for 2h, cool to 20°C, add petroleum ether to precipitate a white solid, filter, and the obtained white Add 60mL of N,N-dimethylformamide (DMF) to...

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Abstract

The invention discloses a 1, 4-2[4-(N, N-p-Methyl-phenyl-amino) styryl] naphthol and the preparation method and application, which belongs to the technology field of photoelectric materials. The structural formula of the component refers to the drawing and the preparation process of the component comprises that: 1-chloromethyl naphthalene reacts with paraformaldehyde and hydrochloric acid under the catalysis of the phosphoric acid to prepare 1, 4- dichloromethylnaphthalene and then reacts with triethyl phosphate to prepare the wittig reagent; the produced wittig reagent reacts with 4-(N, N-2 p-Methyl-phenyl-amino) aminotenzaldehyde under the action of alkali to gain the starting material. The component mixes with bisphenol A Pc resin or bisphenol Z Pc resin to prepare the hole-transporting layer thin film of the organic photoconductor of function separated type. The invention has moderate reaction conditions and has high photosensitivity of the organic photoconductor appliance as the hole-transporting material.

Description

technical field [0001] The invention relates to 1,4-bis[4-(N,N-p-methylphenylamino)styryl]naphthalene and its preparation method and application, belonging to the technical field of photoelectric materials. Background technique [0002] Hole transport materials are a class of organic semiconductor materials that can transport holes. Commonly used in organic photoconductor devices (OPC), organic electroluminescent devices (OLED) and organic solar cells and other fields. Commonly used hole transport materials are hydrazone 4-(N,N-di-p-methylphenyl)aminobenzaldehyde-1,1-diphenylhydrazone (CT106) and butadiene 1,4-bis(p-di Ethylaminophenyl)-4-(α-naphthyl)-4-phenyl-1,3-butadiene (CT8), the structure is as follows: [0003] [0004] Although this type of material is easy to synthesize, due to its high polarity, it cannot be used for resins such as bisphenol Z Pc resins that are soluble in non-polar solutions, and it is easy to crystallize and decompose. [0005] Triarylamine...

Claims

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Application Information

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IPC IPC(8): C07C211/54C07C209/68H01L51/54
Inventor 李祥高尤静王世荣
Owner TIANJIN UNIV
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