Conjugated polymer, preparation method and applications thereof

A technology of conjugated polymers and compounds, applied in chemical instruments and methods, semiconductor/solid-state device manufacturing, organic chemistry, etc., to achieve the effect of increasing the light absorption range and reducing the energy gap

Inactive Publication Date: 2014-12-17
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, benzo[1,2-b:3,4-b’:5,6-d’’]trithiophene is rarely reported in the literature

Method used

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  • Conjugated polymer, preparation method and applications thereof
  • Conjugated polymer, preparation method and applications thereof
  • Conjugated polymer, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
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preparation example Construction

[0037] The present invention also includes the preparation method to above-mentioned conjugated polymer, and this method comprises the following steps:

[0038] a) provide the following compounds A and B;

[0039] Compound A is

[0040] Compound B is

[0041] b) Under an inert gas atmosphere, add the compound A and the compound B into the organic solvent at a molar ratio of 1:1.1 to 1.5, remove the residual oxygen by bubbling, then quickly add the catalyst, and remove the residual oxygen by bubbling again , carry out the Stille coupling reaction at 60-120°C for 24-72 hours, separate and purify to obtain the conjugated polymer (P);

[0042]

[0043] Among them, R 1 for C 6 ~C 15 the alkyl group, R 2 for H or C 1 ~C 16 Alkyl, R 3 for C 1 ~C 17 Alkyl group, n is a natural number between 5 and 60. The reaction formula is as follows:

[0044]

[0045] The catalyst may be tetrakis(triphenylphosphine)palladium or bis(triphenylphosphine)palladium dichloride; or ...

Embodiment 1

[0059] The conjugated polymer disclosed in this example is specifically compound P1, and its structural formula is as follows:

[0060]

[0061] One, the preparation of compound A1:

[0062] 1) Synthesis of 2,3-dibromo-5-nonanoylthiophene (b1)

[0063] In an ice-salt bath, 2.42g (10mmol) 2,3-dibromothiophene (a), 1.95g (11mmol) nonanoyl chloride and 20ml dichloromethane were successively added to the reaction flask, cooled to 0°C, and 1.73 After dissolving g (13 mmol) of aluminum trichloride with 10 ml of dichloromethane, it was slowly dropped into the reaction mixture through a constant pressure dropping funnel. After the dropwise addition was completed, stir at 0° C. for 2 h, then slowly pour 40 ml (2 mol / L) of glacial hydrochloric acid into the solution to quench the reaction. After the reaction solution was extracted with ether, dried over anhydrous magnesium sulfate, and the organic solvent was removed by rotary evaporation, the crude product was obtained. After vacu...

Embodiment 2

[0078] The conjugated polymer disclosed in this example is specifically compound P2, and its structural formula is as follows:

[0079]

[0080] One, the preparation of compound A2:

[0081] 1) Synthesis of 2,3-dibromo-5-nonanoylthiophene (b2)

[0082] In an ice-salt bath, 2.42g (10mmol) 2,3-dibromothiophene (a), 3.17g (11 mmol) heptadecanoyl chloride and 60ml 1,2-dichloroethane were successively added to the reaction flask to make Cool to 0 °C. After dissolving 1.73g (13mmol) of aluminum trichloride in 10ml of dichloromethane, it was slowly dropped into the reaction mixture through a constant pressure dropping funnel. After the dropwise addition was completed, after stirring at 0° C. for 2 h, slowly pour 40 ml of 2M ice hydrochloric acid to quench the reaction. After the reaction solution was extracted with ether, dried over anhydrous magnesium sulfate, and the organic solvent was removed by rotary evaporation, the crude product was obtained. After vacuum drying, no fur...

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Abstract

The invention relates to a conjugated polymer represented by the formula (P); wherein the R1 represents an alkyl group with a carbon number of 6 to 15, the R2 represents an H atom or an alkyl group with a carbon number of 1 to 16, the R3 represents an alkyl group with a carbon number of 1 to 17, and n is a natural number in a range of 5 to 60. The invention also relates to a preparation method and applications of the conjugated polymer. An acyl group is introduced into the a-position on one thiophene ring of benzotrithiophene, and then the length of alkanoyl can be adjusted so as to modulate the solubility and electron density of the conjugated polymer. Dithienobenzooxadiazole is an excellent electron acceptor unit. Benzotrithiophene is taken as the donor unit, an electron pushing-pulling effect between the donor unit and the strong electron acceptor unit (dithienobenzooxadiazole) reduces the energy gap of the conjugated polymer, and thus the light absorption range of the conjugated polymer is largely increased.

Description

technical field [0001] The invention relates to the field of luminescent materials, in particular to a conjugated polymer. The invention also relates to the preparation method and application of the conjugated polymer. Background technique [0002] Due to the advantages that organic solar cells cannot match with inorganic solar cells, such as low cost, simple manufacturing process, light product weight, and large-area flexible preparation, it has attracted widespread attention as a potential renewable energy source. . The performance of organic solar cells has steadily improved over the past decade, with energy conversion efficiencies approaching 10%. Although the energy conversion efficiency of organic solar cells has been greatly improved, so far, the photoelectric conversion efficiency of organic solar cells is still much lower than that of inorganic solar cells. Therefore, in order to realize the commercialization of organic solar cells, the development of new organic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C07D519/00C09K11/06H01L51/46H01L51/54H01L51/30
CPCY02E10/549
Inventor 周明杰管榕李满园
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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