Highly-soluble high-performance semiconductor conjugated polymer and synthetic method thereof

A conjugated polymer, high solubility technology, applied in semiconductor devices, semiconductor/solid-state device manufacturing, electric solid-state devices, etc., can solve the research and application of high-performance semiconductor conjugated polymers, high-performance semiconductor conjugated polymerization Less matter, affecting human health and other issues, to achieve the effect of improving charge transport performance, improving solubility, and improving electrical performance

Inactive Publication Date: 2019-06-04
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the processing of most high-performance semiconducting conjugated polymers will use toxic solvents such as chloroform and chlorobenzene, and the use of these solvents will not only affect human health, but also pollute the environment
However, there are very few high-performance semiconducting conjugated polymers that can be processed by non-chlorinated solvents reported in the literature, mainly for DPP (diketopyrrolopyrrole) backbone engineering, such as asymmetric structures (Adv.Mater.2016 ,28,943–950) and random copolymerization (Adv.Funct.Mater.2015,25,4844–4850), which greatly limit the research and application of solution-processable high-performance semiconducting conjugated polymers

Method used

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  • Highly-soluble high-performance semiconductor conjugated polymer and synthetic method thereof
  • Highly-soluble high-performance semiconductor conjugated polymer and synthetic method thereof
  • Highly-soluble high-performance semiconductor conjugated polymer and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1, synthetic polymer PIID-C 5 -Si 7

[0031] like figure 2 Shown, the isoindigo dibromomonomer IID-C used in this embodiment 5 -Si 7 The synthesis method is as follows:

[0032] Sodium hydrogen gas (7.4 mmol) was added to a solution of 6,6'-dibromoisoindigo (3.1 mmol) in anhydrous DMF (25 mL) under ice bath condition. After 20 minutes, 5-bromo-1-pentene (7.4 mmol) was injected through a septum under nitrogen. The mixture was poured into water (200 mL) and stirred at room temperature for 3 hours. use CH 2 Cl 2 The organic phase was extracted, washed with brine, and washed with MgSO 4 dry. The crude product was washed three times with methanol (100 mL) to give the product IID-C as a dark red solid 5 .

[0033] Under the protection of nitrogen, the compound IID-C 5 (1.8mmol) was dissolved in anhydrous toluene (20mL). Pentamethylsilylhydrogen (4.4 mmol) was injected via a sterile syringe, followed by the addition of a drop (50 μL) of Karstedt's cat...

Embodiment 2

[0036] Embodiment 2, synthetic polymer PIID-C 6 -Si 7

[0037]The isoindigo dibromomonomer IID-C used in this embodiment 6 -Si 7 The synthesis method is as follows:

[0038] Sodium hydrogen gas (7.4 mmol) was added to a solution of 6,6'-dibromoisoindigo (3.1 mmol) in anhydrous DMF (25 mL) under ice bath condition. After 20 minutes, 6-bromo-1-hexene (7.4 mmol) was injected through a septum under nitrogen. The mixture was poured into water (200 mL) and stirred at room temperature for 3 hours. use CH 2 Cl 2 The organic phase was extracted, washed with brine, and washed with MgSO 4 dry. The crude product was washed three times with methanol (100 mL) to give the product IID-C as a dark red solid 6 .

[0039] Under the protection of nitrogen, the compound IID-C 6 (1.8mmol) was dissolved in anhydrous toluene (20mL). Pentamethylsilylhydrogen (4.4 mmol) was injected via a sterile syringe, followed by the addition of a drop (50 μL) of Karstedt's catalyst (platinum divinylte...

Embodiment 3

[0042] Embodiment 3, synthetic polymer PIID-C 7 -Si 7

[0043] The isoindigo dibromomonomer IID-C used in this embodiment 7 -Si 7 The synthesis method is as follows:

[0044] Sodium hydrogen gas (7.4 mmol) was added to a solution of 6,6'-dibromoisoindigo (3.1 mmol) in anhydrous DMF (25 mL) under ice bath condition. After 20 minutes, 7-bromo-1-heptene (7.4 mmol) was injected through a septum under nitrogen. The mixture was poured into water (200 mL) and stirred at room temperature for 3 hours. use CH 2 Cl 2 The organic phase was extracted, washed with brine, and washed with MgSO 4 dry. The crude product was washed three times with methanol (100 mL) to give the product IID-C as a dark red solid 7 .

[0045] Under the protection of nitrogen, the compound IID-C 6 (1.8mmol) was dissolved in anhydrous toluene (20mL). Pentamethylsilylhydrogen (4.4 mmol) was injected via a sterile syringe, followed by the addition of a drop (50 μL) of Karstedt's catalyst (platinum divinyl...

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PUM

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Abstract

The invention discloses a highly-soluble high-performance semiconductor conjugated polymer and a synthetic method thereof. By introducing length-adjustable long straight hybrid siloxy group chain as aside chain, a series of highly-soluble high-performance bioxindol conjugated polymers are obtained. The synthesized novel high-performance semiconductor conjugated polymer can be used as a hole charge transfer material and applied to organic field-effect transistors. The semiconductor conjugated polymer of the invention has great solubility, and can be dissolved in solvents such as chloroform, toluene, hexane and ethyl acetate, etc. The invention is of great guiding significance for designing and synthesizing the high-performance semiconductor conjugated polymer for non-chlorine solvent processing.

Description

technical field [0001] The invention belongs to the field of conjugated polymers, and in particular relates to a highly soluble and high-performance semiconductor conjugated polymer and a synthesis method thereof. Background technique [0002] Due to the advantages of light weight, low cost and good flexibility, conjugated polymers are expected to be widely used in organic field effect transistors. The most studied of the conjugated polymers is the donor-acceptor (D-A) conjugated polymer, which is due to the push-pull interaction between the donor and the acceptor of the D-A conjugated polymer that enhances the intramolecular and intermolecular interactions. force, greatly improving the charge transport performance. However, the processing of most high-performance semiconducting conjugated polymers will use toxic solvents such as chloroform and chlorobenzene, and the use of these solvents will not only affect human health, but also pollute the environment. However, there a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/30
Inventor 邱龙臻丁亚飞姚宏兵王晓鸿
Owner HEFEI UNIV OF TECH
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