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Condensed dinaphthalene-based micromolecular functional material and preparation method and application thereof

A technology of functional materials and small molecules, used in semiconductor/solid-state device manufacturing, photovoltaic power generation, instruments, etc., can solve the problems of low electron mobility and energy conversion rate, complex processing technology, weak processing performance and light absorption performance, etc. The effect of high electron mobility, overcoming complex processing technology, and good energy conversion efficiency

Inactive Publication Date: 2021-08-10
SHENZHEN LEPUTAI TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The invention provides a class of small molecule functional materials based on condensed dinaphthalene and its preparation method and application, aiming to solve the problem of weak processing performance and light absorption performance of the solution, low electron mobility and energy conversion rate, and simultaneous processing in existing materials. complex process issues

Method used

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  • Condensed dinaphthalene-based micromolecular functional material and preparation method and application thereof
  • Condensed dinaphthalene-based micromolecular functional material and preparation method and application thereof
  • Condensed dinaphthalene-based micromolecular functional material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Such as figure 1 and image 3 : For the small molecule functional material CRIC based on condensed dinaphthalene, the structural formula is:

[0034]

[0035] Concrete synthetic steps are as follows:

[0036]

[0037] (1), under nitrogen protection, compound A1 (0.96g, 2mmol), bromothiophene ester compound (1.4g, 6mmol) and Pd(PPh3) 4 (50mg, 0.04mmol) were added in 25mL of anhydrous toluene, And add 8mL of ethanol and potassium carbonate (1M, 3mL), and then the reaction was heated to reflux at 110°C for 24h. After the reaction was cooled to room temperature, it was poured into ethanol to precipitate, filtered, and dried to obtain compound A2 (0.89g, 81%) ;

[0038] (2), under nitrogen protection and -78 ° C, p-hexylbromobenzene (1.2g, 5mmol) was dissolved in 20mL of anhydrous THF, then n-BuLi (2mL, 5mmol) was added dropwise, and stirred for 1 Then, compound A2 (0.44g, 0.82mmol) was added dropwise into the system, the reaction was moved to room temperature, sti...

Embodiment 2

[0042] As shown in Table 1: Polycarbonate (PCZ-300) is dissolved in THF to form a film-forming agent solution with a mass concentration of 10%; take 500 grams of 10% PCZ-300 solution, add 5 grams of CRIC, fully stir and dissolve with THF, and form Coating solution: apply the coating solution on the surface of the aluminum base of φ24*L250mm by dip coating, and dry it for 2 hours to obtain a single-layer organic photosensitive drum with a photosensitive layer thickness of 15 μm.

Embodiment 3

[0044] Such as figure 1 and image 3 : For the small molecule functional material CRIC-4F based on condensed dinaphthalene, the structural formula is:

[0045]

[0046] Concrete synthetic steps are as follows:

[0047] Under nitrogen protection, compound A1 (0.96g, 2mmol), bromothiophene ester compound (1.4g, 6mmol) and Pd(PPh3)4 (50mg, 0.04mmol) were added to 25mL of anhydrous toluene, and 8mL of ethanol was added and potassium carbonate (1M, 3mL). Then the reaction was heated to reflux at 110° C. for 24 h, and the reaction was cooled to room temperature, poured into ethanol for precipitation, filtered, and dried to obtain compound A2 (0.89 g, 81%);

[0048] (2), under nitrogen protection and -78 ° C, p-hexylbromobenzene (1.2g, 5mmol) was dissolved in 20mL of anhydrous THF, then n-BuLi (2mL, 5mmol) was added dropwise, and stirred for 1 Then, compound A2 (0.44g, 0.82mmol) was added dropwise into the system, the reaction was moved to room temperature, stirred overnight, ...

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Abstract

The invention is applicable to the technical field of small molecular functional materials, and provides a condensed dinaphthalene-based micromolecular functional material and a preparation method and application thereof, the condensed dinaphthalene-based micromolecular functional material comprises CRIC, and the preparation method comprises the following steps: S001, in an inert gas atmosphere, Suzuki reaction is performed on a compound 1 and a bromo-ester compound to obtain a compound 2; s002, in the inert gas atmosphere, the compound 2 is subjected to ring closing in the acid environment, and a compound 3 is obtained; s003, in the inert gas atmosphere, the compound 3 is subjected to a Vilesmeier reaction, and a compound 4 is obtained; s004, under the inert gas atmosphere, the compound 4 is subjected to a Knoevenagel condensation reaction, and a final product 5 is obtained. The problems that a traditional material solution is poor in processability and light absorption performance, low in electron mobility and energy conversion rate and complex in processing technology are solved.

Description

technical field [0001] The invention belongs to the field of small molecule functional materials, in particular to a class of small molecule functional materials based on condensed dinaphthalene and its preparation method and application. Background technique [0002] The organic photosensitive drum is the core component of laser printers and electrostatic copies. It is mainly composed of a charge generation layer, a charge transport layer, a protective layer and an aluminum substrate. Among them, the charge generation layer mainly adopts a type of Responsive photosensitive materials, these materials will generate electron-hole pairs after being illuminated, and then transfer to the surface of the organic photosensitive drum to change the charge distribution on the surface, thereby forming an electrostatic latent image. Therefore, the charge generation layer material is very important for the organic photosensitive drum. important. [0003] The existing charge generation la...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/06H01L51/42H01L51/46G03G5/047
CPCC07D495/06G03G5/047H10K85/615H10K85/6576H10K30/00Y02E10/549
Inventor 孟鸿刘继锋赵佳钧沈光夫刘志军邢星罗丰羊辉
Owner SHENZHEN LEPUTAI TECH CO LTD
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