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Dithienothiophene-naphthyl tetracarboxylic diimide conjugated polymer and preparation method and application thereof

A naphthalene tetracarboxylic acid diimide, conjugated polymer technology, applied in the field of solar cell devices and organic electroluminescent devices, dithienothiophene-naphthalene tetracarboxylic acid diimide conjugated polymer, can Solve the problem of low carrier mobility

Inactive Publication Date: 2014-05-14
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing naphthalene tetracarboxylic acid diimide derivatives have low carrier mobility

Method used

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  • Dithienothiophene-naphthyl tetracarboxylic diimide conjugated polymer and preparation method and application thereof
  • Dithienothiophene-naphthyl tetracarboxylic diimide conjugated polymer and preparation method and application thereof
  • Dithienothiophene-naphthyl tetracarboxylic diimide conjugated polymer and preparation method and application thereof

Examples

Experimental program
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preparation example Construction

[0062] The preparation method of the dithienothiophene-naphthalene tetracarboxylic acid diimide conjugated polymer of one embodiment, such as figure 1 shown, including the following steps:

[0063] Step S100, providing compound A and compound B represented by the following structural formula.

[0064] A is: B is:

[0065] Among them, R 1 for C 1 ~C 20 Alkyl groups or aromatic groups with the following structure:

[0066]

[0067] R 2 , R 3 , R 4 for H, C 1 ~C 20 Alkyl or C 1 ~C 20 of alkoxy.

[0068] Wherein the preparation of compound A comprises the following steps:

[0069] To a solution of 2,6-dibromo-dithieno[3,2-b:2',3'-d]thiophene in tetrahydrofuran at -78°C, add n-butyllithium, The molar ratio of [3,2-b:2',3'-d]thiophene to n-butyllithium is 1:3, after warming up to room temperature, stirring and reacting for 0.5 hours, cooling to -78°C and adding trimethyl chloride Tin (Me 3 SnCl) reaction, heated to room temperature and reacted for 24 hours to ...

Embodiment 1

[0100] This embodiment discloses a dithienothiophene-naphthalene tetracarboxylic acid diimide conjugated polymer with the following structure:

[0101]

[0102] n=39.

[0103] The preparation steps of above-mentioned dithienothiophene-naphthalene tetracarboxylic acid diimide conjugated polymer are as follows:

[0104] 1. Synthesis of compound 2,6-bistrimethyltin-dithieno[3,2-b:2',3'-d]thiophene:

[0105]

[0106] t-BuLi (5.3mL, 1.4mol / L, 7.5mmol) was added dropwise to 2,6-dibromo-dithieno[3,2-b:2',3'-d at -78°C ] Thiophene (2.5mmol, 0.885g) in tetrahydrofuran solution (100mL). The mixture was slowly returned to room temperature and stirred for 0.5 h. Then cooled to -78°C, trimethyltin chloride (7.5mmol, 7.5mL) was added dropwise to the above solution. Slowly return to room temperature and stir overnight. The above reaction solution was quenched with water, tetrahydrofuran was removed by rotary evaporation, extracted with chloroform / water, washed with water, and drie...

Embodiment 2

[0117] This embodiment discloses a dithienothiophene-naphthalene tetracarboxylic acid diimide conjugated polymer with the following structure:

[0118]

[0119] n=73.

[0120] The preparation steps of above-mentioned dithienothiophene-naphthalene tetracarboxylic acid diimide conjugated polymer are as follows:

[0121] 1. The synthesis of the compound 2,6-bistrimethyltin-dithieno[3,2-b:2',3'-d]thiophene is the same as in Example 1.

[0122] 2. Preparation of N,N'-di-(n-eicosyl)-2,6-dibromo-1,4,5,8-naphthalene tetracarboxylic acid diimide:

[0123]

[0124] Under nitrogen, n-eicosylamine (0.30 g, 1 mmol) was added to propionic acid ( 15mL) solution, refluxed overnight. After cooling to room temperature, the reaction solution was poured into aqueous sodium hydroxide solution and extracted with chloroform. The organic solvent was removed, washed with ethyl acetate, dissolved in chloroform, and then column chromatographed (alumina column). Removal of solvent gave a solid...

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Abstract

The invention discloses a dithienothiophene-naphthyl tetracarboxylic diimide conjugated polymer with a structural formula shown in the specification, wherein n is an integer from 2 to 200; R1 is a C1-C20 alkyl group or an aromatic group with a structure shown in the specification; R2, R3 and R4 are H, C1-C20 alkyl group or C1-C20 alkoxy group. The carrier mobility of the dithienothiophene-naphthyl tetracarboxylic diimide conjugated polymer is relatively high. The invention also provides a preparation method of the dithienothiophene-naphthyl tetracarboxylic diimide conjugated polymer, and a solar cell device, an organic electroluminescence device and an organic field effect transistor using the dithienothiophene-naphthyl tetracarboxylic diimide conjugated polymer.

Description

technical field [0001] The present invention relates to a dithienothiophene-naphthalene tetracarboxylic diimide conjugated polymer, a preparation method thereof and a solar cell device using the dithienothiophene-naphthalene tetracarboxylic diimide conjugated polymer and organic electroluminescent devices. Background technique [0002] The energy issue is a major issue of great concern to all countries in the world. Solar energy is the most ideal alternative energy source for humans in the future, and solar cells that convert solar energy into electrical energy are also research hotspots. Conjugated polymer thin film solar cells emerging in recent years have outstanding advantages such as low cost, light weight, simple manufacturing process, and can be prepared into flexible devices. In addition, organic materials are diverse and highly designable, promising to improve the performance of solar cells through material design and optimization. [0003] Naphthalene tetracarbo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/46H01L51/54H01L51/30
CPCY02E10/549
Inventor 周明杰管榕李满园黄佳乐黎乃元
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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