Unlock instant, AI-driven research and patent intelligence for your innovation.

Pyrrolopyrrolidinedione based copolymer, preparation method and applications thereof

A pyrrolopyrrolidinedione-based copolymer and pyrrolopyrrolidinedione-based technology are applied in semiconductor/solid-state device manufacturing, electric solid-state devices, semiconductor devices, etc., and can solve the problem of low conversion efficiency and low load of inorganic solar cells. The collection efficiency and spectral response mismatch of the current electrode can achieve the effects of novel material structure, high photoelectric conversion efficiency and strong fluorescence performance.

Inactive Publication Date: 2015-04-15
OCEANS KING LIGHTING SCI&TECH CO LTD +2
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since 1992, N.S. Sariciftci et al. reported on SCIENCE (N.S Sariciftci, L. Smilowitz, A.J. Heeger, et al. Science, 1992, 258, 1474) that conjugated polymers and C 60 After the phenomenon of light-induced electron transfer between polymer solar cells, people have invested a lot of research in polymer solar cells and achieved rapid development, but the conversion efficiency is still much lower than that of inorganic solar cells.
The main constraints that limit the improvement of performance are: the spectral response of organic semiconductor materials does not match the spectrum of solar radiation, the relatively low carrier mobility of organic semiconductors, and the low electrode collection efficiency of carriers, etc.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Pyrrolopyrrolidinedione based copolymer, preparation method and applications thereof
  • Pyrrolopyrrolidinedione based copolymer, preparation method and applications thereof
  • Pyrrolopyrrolidinedione based copolymer, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: The pyrrolopyrrolidine diketone-based copolymer of this example, that is, poly{2,2′-(9,10-bis(n-octyloxy)phenanthrene-2,7-diyl-co-3 ,6-bis(5-yl-2-thienyl)-2,5-dihydro-2,5-di-n-octylpyrrolo[3,4-c]pyrrole-1,4-dione} (P1 ), (where R1 is n-octyl, R2 is n-octyl, n=63), and its structural formula is as follows:

[0029]

[0030] The preparation steps of above-mentioned polymer are as follows:

[0031] The reaction formula is as follows:

[0032]

[0033] Under argon protection, 2,2'-(9,10-bis(n-octyloxy)phenanthrene-2,7-bispinacol borate (137mg, 0.2mmol), 3,6-bis( 5-bromo-2-thienyl)-2,5-dihydro-2,5-di-n-octylpyrrolo[3,4-c]pyrrole-1,4-dione (136.4mg, 0.2mmol) was added In the flask filled with 10ml of toluene solvent, after fully dissolving, potassium carbonate (2mL, 2mol / L) solution was added into the flask, vacuumized to deoxygenate and filled with argon, then added bistriphenylphosphine palladium dichloride ( 5.6mg, 0.008mmol); the flask was heated to 1...

Embodiment 2

[0036] Example 2: The pyrrolopyrrolidinedione-based copolymer of this example, that is, poly{2,2′-(9,10-di(methoxy)phenanthrene-2,7-diyl-co-3, 6-bis(5-yl-2-thienyl)-2,5-dihydro-2,5-di-n-eicosylpyrrolo[3,4-c]pyrrole-1,4-dione}( P2), (where R1 is methyl, R2 is n-eicosyl, n=10), its structural formula is as follows:

[0037]

[0038] The preparation steps of above-mentioned polymer are as follows:

[0039] The reaction formula is as follows:

[0040]

[0041]Under the protection of a mixed gas of nitrogen and argon, 2,2'-(9,10-di(methoxy)phenanthrene-2,7-dipinacol borate (147mg, 0.3mmol), 3,6- Bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di-n-eicosylpyrrolo[3,4-c]pyrrole-1,4-dione (306mg, 0.3 mmol) and 15mL tetrahydrofuran into a 50mL two-neck bottle, fully dissolved, and then pass a mixture of nitrogen and argon to exhaust the air for about 20 minutes, then add tetrakistriphenylphosphine palladium (4mg, 0.003mmol) into it, fully dissolve Then add sodium bicarbonate (3mL, 2mo...

Embodiment 3

[0043] Example 3: The pyrrolopyrrolidinedione-based copolymer of this example, that is, poly{2,2′-(9,10-bis(n-eicosyloxy)phenanthrene-2,7-diyl-co -3,6-bis(5-yl-2-thienyl)-2,5-dihydro-2,5-dimethylpyrrolo[3,4-c]pyrrole-1,4-dione}( P3), (where R1 is n-eicosyl, R2 is methyl, n=78), its structural formula is as follows:

[0044]

[0045] The preparation steps of above-mentioned polymer are as follows:

[0046] The reaction formula is as follows:

[0047]

[0048] Under nitrogen protection, 2,2′-(9,10-bis(n-eicosyloxy)phenanthrene-2,7-dipinacol borate (307mg, 0.3mmol), 3,6-bis( 5-bromo-2-thienyl)-2,5-dihydro-2,5-dimethylpyrrolo[3,4-c]pyrrole-1,4-dione (160.4mg, 0.33mmol), acetic acid Palladium (3.5mg, 0.015mmol) and tri(o-methylphenyl)phosphine (21mg, 0.06mmol) were added into a flask filled with 12mL of N,N-dimethylformamide, and potassium carbonate ( 3mL, 2mol / L) solution, and then pass nitrogen into the flask to exhaust the air for about 30min; heat the flask to 130°C f...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
Thicknessaaaaaaaaaa
Thicknessaaaaaaaaaa
Login to View More

Abstract

The invention belongs to the field of organic solar cell materials, and discloses a pyrrolopyrrolidinedione based copolymer, a preparation method and applications thereof. The structural formula of the material is shown in the description, in the formula, the R1 and R2 both represents a C1-C20 alkyl group, and n is an integer in a range of 10 to 78. In the pyrrolopyrrolidinedione based copolymer, the diketopyrrolopyrrole (DPP) unit has the advantages of strong absorbing performance and photochemical stability, moreover, the N atoms of DPP can be modified by an alkyl chain, when the length of thiophene, which is connected to the 3rd and 6th positions of DPP, is increased, the absorption range is enlarged, and at the same time the energy gap is narrowed down. Phenanthrene is a compound with a large planar rigid structure and has high thermal stability and fluorescence quantum yield. The light conversion rate of organic solar cell devices can be improved by applying the provided pyrrolopyrrolidinedione based copolymer to the organic solar cells.

Description

technical field [0001] The invention relates to the field of organic solar cell materials, in particular to a pyrrolopyrrolidine diketone-based copolymer and its preparation method and application. Background technique [0002] The preparation of low-cost and high-efficiency solar cells using cheap materials has always been a research hotspot and difficulty in the field of photovoltaics. Due to the complex production process and high cost of silicon cells currently used on the ground, their application is limited. In order to reduce the cost of batteries and expand the application range, people have been looking for new solar cell materials for a long time. Organic semiconductor materials have attracted much attention due to the advantages of readily available raw materials, low cost, simple preparation process, good environmental stability, and good photovoltaic effect. Since 1992, N.S. Sariciftci et al. reported on SCIENCE (N.S Sariciftci, L. Smilowitz, A.J. Heeger, et a...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C08G61/12H01L51/46
CPCY02E10/549
Inventor 周明杰张振华王平陈吉星
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com