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

A technology of methylphenylamino and styrene-based, applied in the preparation of amino compounds from amines, semiconductor/solid-state device manufacturing, electrical components, etc., can solve the problems of high polarity, achieve high hole transfer ability, and mild reaction conditions , the effect of easy preparation

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

[0008] Although this type of material is easy to synthesize, it is insoluble in non-polar solvents due to its high polarity. Since bisphenol Z Pc resin can only be dissolved in non-polar solvents, this material is difficult to mix with bisphenol Z Pc resin.

Method used

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

[0022] Add 9g of 1-methylnaphthalene and 8.5mL of glacial acetic acid into a 250mL four-neck flask, while stirring, add 3.5g of paraformaldehyde, 5mL of phosphoric acid, and 12mL of concentrated hydrochloric acid with a mass fraction of 37%, stir at 80°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, filter out the purple solid, and 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 5.4g of white solid (44% yield) 1-methyl -4-Chloromethylnaphthalene, melting point 28°C

[0023] Add 5.4g of 1-methyl-4-chloromethylnaphthalene to a 200mL four-neck flask, reflux 6mL of triethyl phosphite at 180°C for 3h, cool to 20°C, ice-bath to below 10°C, add 40mL of N, N-dimethylformamide (DMF), add 2.5g sodium methylate while stirring, then dropwise add...

Embodiment 2

[0027] Add 9g of 1-methylnaphthalene and 8.5mL of glacial acetic acid into a 250mL four-neck flask, add 3.5g of paraformaldehyde, 5mL of phosphoric acid, and 24mL (37%) of concentrated hydrochloric acid while stirring, stir at 80°C for 3h, 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, filter out the purple solid, and 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 4.2g of a white solid (yield 34.5%) with a melting point of 28°C

[0028] Add 4.2g of 1-methyl-4-chloromethylnaphthalene to a 200mL four-neck flask, reflux 6mL of trihexyl phosphite at 180°C for 2h, cool to 20°C, and ice-bath to below 10°C, add 30mL of N, N-dimethylformamide (DMF), add 3g potassium tert-butoxide while stirring, then dropwise add 30mL (mass concentration 0.095%) of 4...

Embodiment 3

[0032] Add 9g of 1-methylnaphthalene, 17mL of glacial acetic acid into a 250mL four-neck flask, add 7g of paraformaldehyde, 10mL of phosphoric acid, and 12mL (37%) of concentrated hydrochloric acid while stirring, stir at 100°C for 4h, then cool to 20°C , add 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, filter out the purple solid, 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 7.0 g of a white solid (yield 57.1%), melting point 28°C

[0033] Add 7.0g 1-methyl-4-chloromethylnaphthalene to a 200mL four-neck flask, reflux 6mL trihexyl phosphite for 3h, cool to 20°C, ice-bath to below 10°C, add 40mL tetrahydrofuran (THF) , Add 2.5g potassium tert-butoxide while stirring, then dropwise add 40mL THF (mass concentration 0.095%) solution, stir for 4h under ice bath, let stand overn...

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Abstract

The invention discloses a 1- methyl-4-[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-methylnaphthalene reacts with paraformaldehyde and hydrochloric acid under the catalysis of the phosphoric acid to prepare 1- methyl-4-chloromethyl naphthalene 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-methyl-4-[4-(N,N-p-methylphenylamino)styryl]naphthalene and its preparation method and application, belonging to the technical field of photoelectric materials. Background technique [0002] Triarylamine groups are easy to form cationic radicals (holes). Materials containing such groups have very low ionization energy and low melting point. They can be formed into films by vacuum evaporation and have good compatibility with Pc resins. Solubility, suitable for preparing the hole transport layer of laser organic photoconductor (OPC) and organic electroluminescent device (OLED), is a kind of good hole transport material. [0003] Currently commonly used are 4,4`-bis(N-p-methylphenyl-N-phenylamino)biphenyl (TPD) and dendritic triarylamine 1,3,5-tris[p-(N,N -diphenyl)aminophenyl]benzene (MTDAT) and the like. [0004] [0005] This material is mainly obtained by the Ullmann reaction or the reaction of aromatic halides and arom...

Claims

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Application Information

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