A kind of perylene imide polymer and its preparation method and application

Abstract

The invention discloses a perylene imide polymer, the structural formula of which is as follows: wherein R is an alkyl group; X is one of H and F atoms. The peryleneimide polymer provided by the present invention takes peryleneimide and carbon-carbon triple bond as repeating units, and is prepared by Stille coupling reaction; the carbon-carbon triple bond exists in the polymer as a conjugated microunit In the chain, the π system of the polymer molecule can be effectively increased, and the content of peryleneimide in the polymer chain can be at a higher position; this is conducive to improving the electron mobility on the one hand, and on the other hand can weaken the molecular The aggregation leads to the increase of the fill factor; the molecule has a wider absorption spectrum than the ordinary D-A type molecule, and the introduction of the F atom also leads to the narrowing of the band gap of the polymer and broadens the absorption range; the polymer is in It has wide and strong absorption in the visible light region, and has higher short-circuit current than unfluorinated polymers, and has better solubility and is easy to process in solution.

Description

Technical field

[0001] The present invention belongs to the field of polymer synthesis, and more particularly to a cyanimide polymer and a preparation method thereof. Background technique

[0002] With the gradual depletion of oil and other fossil energy and environmental pollution problems, the development and application of renewable energy such as solar energy has gradually become a hot spot for research, and the most effective way to use solar energy is mainly to develop solar cells. Traditional silicon-based solar cell cost is high, and the energy is more time, the preparation procedures are complex, and pollution is easily produced during the production process. In contrast, the organic solar cell has a high quality, low cost, and a large area of ​​solution, which can be made with flexible devices. Therefore, research and development has high efficiency organic solar cell active layer materials increasingly being interested in major scientific research workers.

[0003] Ami...

Examples

Embodiment 1

[0032] A phosphimide polymer, a reaction route is shown in formula III, and the preparation method thereof includes the following steps:

[0033] Take bis (trimethyl tin) acetylene (82 mg, 0.23 mmol) and N, N'-di (1-pentylhexyl) -1,7-bromide (200 mg, 0.23 mmol), three (Dibenzyl acetone) dual palladium (PD 2 (DBA) 3 , 4.3mg, 4.7 μmol and triphenylphosphine (p (o-tol) 3 5.2 mg, 17 μmol) In a 25 mL single-mouth flask, 5 ml of toluene was injected into the reaction system under nitrogen protection with a syringe by a syringe, and then warmed to 120 ° C and stirred vigorously for 48 h; The resulting polymer product system is then closed, and 100 mg 2-tributyl methylthiophene reaction is injected into the resulting product system under nitrogen protection, and then 200 mg of 3-bromothiophene reaction 12h is injected into the system, then the crude product Precipitation with methanol; use ethyl acetate, acetone and dichloromethane, remove the oligomers and catalysts in addition to the ol...

Embodiment 2

[0036] A phymide polymer, a reaction route, a preparation method thereof specifically includes the steps of:

[0037] Take bis (trimethyl tin) acetylene (136.6 mg, 0.39 mmol) and N, N'-di (2-ethylhexyl) -1,7-dibromo-6,12-difluoroimide ( 300mg, 0.39mmol), tris (dibenzyl acetone) di palladium (PD 2 (DBA) 3 , 4.5mg, 4.9 μmol) and tri-toromylphosphine (p (o-tol) 35 mg, 16 μmol) in a 25 ml single-mouth flask, after extracting the oxygen in the system via nitrogen gas, 6 ml of toluene is injected into the reaction system under nitrogen protection, warmed to 120 ° C, stirred vigorously for 48h, then the resulting The polymer product system performs a blocking treatment, and 100 mg of 2-tributyl methylthiophene reaction is injected under nitrogen protection, and then 200 mg of 3-bromothiophene reaction 12h is injected into the system, then the crude product is precipitated with methanol. Ethyl acetate, acetone and dichloromethane were subjected to extracting the coarse product, and the ol...

Embodiment 3

[0040] A phymide-based polymer, a reaction route, a preparation method thereof, specifically comprising the steps of:

[0041] Take bis (trimethyl tin) acetylene (71 mg, 0.2 mmol) and N, N'-di (1-pentylhexyl) -1,7-dibromo-6,12-difluoro-osmia ( 180mg, 0.2mmol), three (dibenzyl acetone) di palladium (PD 2 (DBA) 3 , 4.2mg, 4.6 μmol) and tri-torne (P (o-tol) 3 4.8 mg, 16 μmol) In a 25 mL single-mouth flask, after the nitrogen gas extraction of the oxygen in the system, 4 ml of toluene was injected with 4 ml of toluene under nitrogen protection, and the temperature was stirred up to 120 ° C, stirred vigorously for 48h, then The resulting polymer product system is closed, and 100 mg of 2-tributyl methylthiophene reaction is injected into the system under nitrogen protection, 200 mg of 3-bromothiophene reaction 12h is injected into the system, and then the crude product is precipitated with methanol. come out. After filtration, the solid was washed with methanol in dichloromethane, and t...

Technical field

[0001] The present invention belongs to the field of polymer synthesis, and more particularly to a cyanimide polymer and a preparation method thereof. Background technique

[0002] With the gradual depletion of oil and other fossil energy and environmental pollution problems, the development and application of renewable energy such as solar energy has gradually become a hot spot for research, and the most effective way to use solar energy is mainly to develop solar cells. Traditional silicon-based solar cell cost is high, and the energy is more time, the preparation procedures are complex, and pollution is easily produced during the production process. In contrast, the organic solar cell has a high quality, low cost, and a large area of ​​solution, which can be made with flexible devices. Therefore, research and development has high efficiency organic solar cell active layer materials increasingly being interested in major scientific research workers.

[0003] Ami...

Examples

Embodiment 1

[0032] A phosphimide polymer, a reaction route is shown in formula III, and the preparation method thereof includes the following steps:

[0033] Take bis (trimethyl tin) acetylene (82 mg, 0.23 mmol) and N, N'-di (1-pentylhexyl) -1,7-bromide (200 mg, 0.23 mmol), three (Dibenzyl acetone) dual palladium (PD 2 (DBA) 3 , 4.3mg, 4.7 μmol and triphenylphosphine (p (o-tol) 3 5.2 mg, 17 μmol) In a 25 mL single-mouth flask, 5 ml of toluene was injected into the reaction system under nitrogen protection with a syringe by a syringe, and then warmed to 120 ° C and stirred vigorously for 48 h; The resulting polymer product system is then closed, and 100 mg 2-tributyl methylthiophene reaction is injected into the resulting product system under nitrogen protection, and then 200 mg of 3-bromothiophene reaction 12h is injected into the system, then the crude product Precipitation with methanol; use ethyl acetate, acetone and dichloromethane, remove the oligomers and catalysts in addition to the ol...

Embodiment 2

[0036] A phymide polymer, a reaction route, a preparation method thereof specifically includes the steps of:

[0037] Take bis (trimethyl tin) acetylene (136.6 mg, 0.39 mmol) and N, N'-di (2-ethylhexyl) -1,7-dibromo-6,12-difluoroimide ( 300mg, 0.39mmol), tris (dibenzyl acetone) di palladium (PD 2 (DBA) 3 , 4.5mg, 4.9 μmol) and tri-toromylphosphine (p (o-tol) 35 mg, 16 μmol) in a 25 ml single-mouth flask, after extracting the oxygen in the system via nitrogen gas, 6 ml of toluene is injected into the reaction system under nitrogen protection, warmed to 120 ° C, stirred vigorously for 48h, then the resulting The polymer product system performs a blocking treatment, and 100 mg of 2-tributyl methylthiophene reaction is injected under nitrogen protection, and then 200 mg of 3-bromothiophene reaction 12h is injected into the system, then the crude product is precipitated with methanol. Ethyl acetate, acetone and dichloromethane were subjected to extracting the coarse product, and the ol...

Embodiment 3

[0040] A phymide-based polymer, a reaction route, a preparation method thereof, specifically comprising the steps of:

[0041] Take bis (trimethyl tin) acetylene (71 mg, 0.2 mmol) and N, N'-di (1-pentylhexyl) -1,7-dibromo-6,12-difluoro-osmia ( 180mg, 0.2mmol), three (dibenzyl acetone) di palladium (PD 2 (DBA) 3 , 4.2mg, 4.6 μmol) and tri-torne (P (o-tol) 3 4.8 mg, 16 μmol) In a 25 mL single-mouth flask, after the nitrogen gas extraction of the oxygen in the system, 4 ml of toluene was injected with 4 ml of toluene under nitrogen protection, and the temperature was stirred up to 120 ° C, stirred vigorously for 48h, then The resulting polymer product system is closed, and 100 mg of 2-tributyl methylthiophene reaction is injected into the system under nitrogen protection, 200 mg of 3-bromothiophene reaction 12h is injected into the system, and then the crude product is precipitated with methanol. come out. After filtration, the solid was washed with methanol in dichloromethane, and t...

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