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Conjugated polymer containing cyclopentadienyl diene dithiophene-naphthalene tetracarboxylic diimide and preparation method and application thereof

A technology of naphthalene tetracarboxylic acid diimide and cyclopentadiene dithiophene, which is applied in chemical instruments and methods, semiconductor/solid-state device manufacturing, luminescent materials, etc., and can solve the mismatch between the spectral response of the device and the solar radiation spectrum , the red light region has not been effectively utilized, low carrier mobility and other problems, to achieve the effect of high carrier mobility, high molar absorptivity, and wide light absorption range

Inactive Publication Date: 2012-01-25
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the research on polymer solar cells mainly focuses on the blending system of donor and acceptor, using PTB7 and PC 71 The energy conversion efficiency of the BM blend system has reached 7.4% (Y.Lianget al., Adv.Mater.; DOI: 10.1002 / adma.200903528), but it is still much lower than the conversion efficiency of inorganic solar cells, which limits polymer solar energy. The main constraints to the improvement of the photoelectric conversion efficiency of batteries are: the relatively low carrier mobility of organic semiconductor devices, the mismatch between the spectral response of the device and the solar radiation spectrum, and the ineffective use of the red light region with high photon flux.

Method used

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  • Conjugated polymer containing cyclopentadienyl diene dithiophene-naphthalene tetracarboxylic diimide and preparation method and application thereof
  • Conjugated polymer containing cyclopentadienyl diene dithiophene-naphthalene tetracarboxylic diimide and preparation method and application thereof
  • Conjugated polymer containing cyclopentadienyl diene dithiophene-naphthalene tetracarboxylic diimide and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Example 1 Preparation of cyclopentadiene-containing dithiophene-naphthalene tetracarboxylic diimide conjugated polymer (n=35, x=1, y=1)

[0052]

[0053] Under the condition of nitrogen protection, compound N, N'-dioctyl-2,6-dibromo-1,4,5,8-naphthalene tetracarboxylic acid diimide (0.32g, 0.5mmol) and 4 , 4-bis(eicosyl)-2,6-bistrimethyltin-cyclopentadiene (2,1-b:3,4-b')dithiophene (0.53g, 0.5mmol) chloride Benzene (25mL) solution was bubbled for 0.5h to remove residual oxygen, and then Pd was added 2 (dba) 3 (0.014g, 0.015mmol) and P(o-Tol) 3 (0.0083g, 0.027mmol), and bubbling for 1h to remove residual oxygen, then heated to 30°C and refluxed for 72h.

[0054] Add the mixed liquid dropwise to methanol for sedimentation, and dissolve it with chlorobenzene after suction filtration, methanol washing and drying steps, add it to the aqueous solution of sodium diethyldithiocarbamate, heat to 80°C and stir overnight. Pass the organic phase through alumina column chromat...

Embodiment 2

[0055] Example 2 Preparation of cyclopentadiene-containing dithiophene-naphthalene tetracarboxylic acid diimide conjugated polymer (n=71, x=1, y=1)

[0056]

[0057] Under argon protection condition, to containing compound N, N'-two-(n-eicosyl)-2,6-dibromo-1,4,5,8-naphthalene tetracarboxylic diimide (0.49 g, 0.5mmol) and 4,4-dioctyl-2,6-bistrimethyltin-cyclopentadiene (2,1-b:3,4-b')dithiophene (0.36g, 0.5mmol ) in chlorobenzene (25mL) solution bubbled for 0.5h to remove residual oxygen, then added Pd 2 (dba) 3 (0.014g, 0.015mmol) and P(o-Tol) 3(0.0083g, 0.027mmol), and bubbling for 1h to remove residual oxygen, then heated to 60°C for 24h under reflux.

[0058] Add the mixed liquid dropwise to methanol for sedimentation, and dissolve it with chlorobenzene after suction filtration, methanol washing and drying steps, add it to the aqueous solution of sodium diethyldithiocarbamate, heat to 80°C and stir overnight. Pass the organic phase through alumina column chromatograph...

Embodiment 3

[0059] Example 3 Preparation of cyclopentadiene-containing dithiophene-naphthalene tetracarboxylic acid diimide conjugated polymer (n=57, x=1, y=1)

[0060]

[0061] Under nitrogen protection conditions, the compound N, N'-bis-(1-octylnonyl)-2,6-dibromo-1,4,5,8-naphthalene tetracarboxylic acid diimide (0.45g , 0.5mmol) and 4,4-dioctyl-2,6-bistrimethyltin-cyclopentadiene (2,1-b:3,4-b')dithiophene (0.36g, 0.5mmol) Chlorobenzene (25mL) solution was bubbled for 0.5h to remove residual oxygen, then added Pd 2 (dba) 3 (0.014g, 0.015mmol) and P(o-Tol) 3 (0.0083g, 0.027mmol), and bubbling for 1h to remove residual oxygen, then heated to 80°C for 48h under reflux.

[0062] Add the mixed solution dropwise to methanol for sedimentation, and dissolve it with chlorobenzene after suction filtration, methanol washing and drying steps, add it to the aqueous solution of sodium diethyldithiocarbamate, heat to 90°C and stir overnight. Pass the organic phase through alumina column chromato...

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Abstract

The invention discloses a conjugated polymer containing cyclopentadienyl diene dithiophene-naphthalene tetracarboxylic diimide, which is characterized by being a compound with the formula shown as below, wherein R1 is C1-C20 alkyl, R2 is C1-C20 alkyl or substituted phenyl, R3, R4 and R5 are identically or differently expressed as hydrogen, C1-C20 alkyl or alkoxy, x is greater than or equal to 1 and less than 2, y is greater than 0 and less than or equal to 1, the sum of x and y is 2 and n is an integer from 1 to 120. The conjugated polymer containing cyclopentadienyl diene dithiophene-naphthalene tetracarboxylic diimide is prepared via Stille with a simple reactive synthesis route and low processing requirements and has better film-forming properties, better thermal stability, high carrier mobility, higher molar absorption coefficient and wide optical absorption range, the degree of matching with solar transmission spectrum is improved, the photoelectric conversion efficiency is increased, and the conjugated polymer has a wide scope of application.

Description

technical field [0001] The present invention relates to the technical field of polymer materials, in particular to a polymer, its preparation and its application, more specifically, to a conjugated polymer containing cyclopentadiene dithiophene-naphthalene tetracarboxylic diimide, Preparation method and its 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. Silicon solar cells currently used on the ground are limited in application due to complex production processes and high costs. In order to reduce the cost and expand the scope of application, people have been looking for new solar cell materials for a long time. Polymer solar cells have attracted much attention because of their advantages such as low raw material prices, light weight, flexibility, simple production process, and large-area preparation by coating, prin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C09K11/06H01L51/46H01L51/54H01L51/30
CPCY02E10/549
Inventor 周明杰黄杰许二建
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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