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Macromolecular compound containing boron-nitrogen coordinate bond, preparation method and application thereof

A technology of polymer compounds and coordination bonds, which is used in semiconductor/solid-state device manufacturing, photovoltaic power generation, electrical components, etc., can solve the problems of slow development, low mobility, poor air stability, etc. Good mobility and flatness

Active Publication Date: 2019-09-13
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In comparison, the development of n-type materials and bipolar materials is relatively slow, with low mobility and poor air stability

Method used

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  • Macromolecular compound containing boron-nitrogen coordinate bond, preparation method and application thereof
  • Macromolecular compound containing boron-nitrogen coordinate bond, preparation method and application thereof
  • Macromolecular compound containing boron-nitrogen coordinate bond, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0096] P-BNBP-DTBT (C24) polymer, the structural formula is as follows (in the structural formula, the capping group is omitted):

[0097]

[0098] The preparation method is: add BNBP dibromomonomer (111.3mg, 0.10mmol), thiophene bridged benzothiadiazole bistin salt (62.6mg, 0.10mmol) and tetrakis(triphenyl Phosphine) palladium (1.2mg, 0.001mmol), then vacuumize the system and ventilate the system with argon for several times, add distilled toluene solvent (15mL) in the dark state, reflux at 115°C for 48h, and then add benzene Boric acid (100mg, 0.82mmol) was continued to reflux for 3h, and bromobenzene (200mg, 1.28mmol) was added to reflux for 12h. The reaction system was settled in methanol while it was hot, and the polymer was precipitated. The precipitate was washed with acetone, n-hexane, and chloroform to remove small molecules and catalysts with a Soxhlet extractor, and finally the polymer was extracted with chlorobenzene. Yield 100.2 mg, 78% yield.

[0099] Elemen...

Embodiment 2

[0103] P-BNBP-DTBT (C28) polymer, the structural formula is as follows (in the structural formula, the capping group is omitted):

[0104]

[0105] The preparation method is: add BNBP dibromomonomer (122.5mg, 0.10mmol), thiophene bridged benzothiadiazole bistin salt (62.6mg, 0.10mmol) and tetrakis(triphenyl Phosphine) palladium (1.2mg, 0.001mmol), then vacuumize the system and ventilate the system several times with argon, add distilled toluene solvent (35mL) in a dark state, reflux at 115°C for 52h, then add phenylboronic acid (100mg, 0.82mmol) was refluxed for 3h, and bromobenzene (200mg, 1.28mmol) was added to reflux for 3h. The reaction system was settled in methanol while it was hot, and the polymer was precipitated. The precipitate was washed with acetone, n-hexane, and chloroform to remove small molecules and catalysts with a Soxhlet extractor, and finally the polymer was extracted with chlorobenzene. Yield 119 mg, 92% yield.

[0106] The elemental analysis of the ...

Embodiment 3

[0109] P-BNBP-DTBT (C32) polymer, the structural formula is as follows (in the structural formula, the capping group is omitted):

[0110]

[0111] The preparation method is: add BNBP dibromomonomer (133.7mg, 0.10mmol), thiophene bridged benzothiadiazole bistin salt (62.6mg, 0.10mmol) and tetrakis (triphenyl Phosphine) palladium (1.2mg, 0.001mmol), then vacuumize the system and ventilate the system several times with argon gas, add distilled toluene solvent (15mL) in a dark state, reflux at 115°C for 48h, then add phenylboronic acid (100mg, 0.82mmol) was refluxed for 3h, and bromobenzene (200mg, 1.28mmol) was added to reflux for 3h. The reaction system was settled in methanol while it was hot, and the polymer was precipitated. The precipitate was washed with acetone, n-hexane, and chloroform to remove small molecules and catalysts with a Soxhlet extractor, and finally the polymer was extracted with chlorobenzene. Yield 110 mg, 74% yield.

[0112] Elemental analysis was ca...

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Abstract

Belonging to the technical field of macromolecular functional materials and organic electronics, the invention provides a macromolecular compound containing boron-nitrogen coordinate bond, a preparation method and application thereof, and solves the technical problem of low mobility of organic conjugated macromolecular compounds in the prior art. The conjugated main chain of the macromolecular compound provided by the invention contains three fragments, namely an electron-deficient double boron-nitrogen coordinate bond bridged bipyridyl unit, an Ar unit and an electron-rich thiophene unit respectively, and the structural formula is shown as formula (I). The macromolecular compound has the characteristics of good planarity, strong crystallinity, strong intermolecular interaction, etc., andcan greatly improve the electron mobility of the material; the chemical structure is easy to modify, the energy level structure is adjustable, and the absorption spectrum is wide; and the macromolecular compound can be applied as the acceptor material of organic solar cells and the charge transport layer material of organic field effect transistors.

Description

technical field [0001] The invention belongs to the technical field of polymer functional materials and organic electronics, and specifically relates to a polymer compound containing boron-nitrogen coordination bonds, a preparation method and application thereof. Background technique [0002] Solar cells are devices that absorb solar energy and convert it into electrical energy. Compared with the existing inorganic silicon solar cells, organic solar cells have attracted much attention due to their outstanding advantages such as flexibility, low cost, and light weight. Most of the early-developed organic solar cell devices are based on fullerene PCBM and its derivatives as acceptor materials. However, the narrow absorption spectrum of PCBM and the difficulty of adjusting the energy level make it difficult to further improve the performance. Therefore, people are vigorously developing non-fullerene acceptor materials. Compared with the widely studied small-molecule fullerene...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/42H01L51/46H01L51/05H01L51/30
CPCC08G61/126C08G2261/124C08G2261/1412C08G2261/3223C08G2261/312C08G2261/344C08G2261/414H10K85/151H10K10/484H10K30/00Y02E10/549
Inventor 刘俊窦传冬赵汝艳王利祥
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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