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[2,1-b:3,4-b'] 2,2'-bithienyl-naphthalene diimide-containing conjugated polymer and preparation method and application thereof

A technology of naphthalene tetracarboxylic acid diimide and conjugated polymer, which is applied in the field of preparation of cyclopentadiene dithiophene-naphthalene tetracarboxylic acid diimide conjugated polymer, and can solve the problem of device spectral response and The solar radiation spectrum does not match, the red light region is not effectively used, and the low carrier mobility and other problems 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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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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  • [2,1-b:3,4-b'] 2,2'-bithienyl-naphthalene diimide-containing conjugated polymer and preparation method and application thereof
  • [2,1-b:3,4-b'] 2,2'-bithienyl-naphthalene diimide-containing conjugated polymer and preparation method and application thereof
  • [2,1-b:3,4-b'] 2,2'-bithienyl-naphthalene diimide-containing conjugated polymer and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Example 1 Preparation of Conjugated Polymer Containing Benzozodithiophene-Naphthalene Tetracarboxylic Diimide (n=48, x=1, y=1)

[0051]

[0052] 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 2 , a solution of 7-bistrimethyltin-4,5-dioctylbenzo[2,1-b:3,4-b']dithiophene (0.37 g, 0.5 mmol) in chlorobenzene (25 mL) was bubbled 0.5h to remove residual oxygen, then add 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 30°C and refluxed for 72h.

[0053] 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 chromatography, rinse with chloroform, ...

Embodiment 2

[0054] Example 2 Preparation of Conjugated Polymer Containing Benzozodithiophene-Naphthalene Tetracarboxylic Diimide (n=41, x=1, y=1)

[0055]

[0056] Under the condition of nitrogen protection, compound N, N'-two-(n-eicosyl)-2,6-dibromo-1,4,5,8-naphthalene tetracarboxylic acid diimide (0.49g , 0.5mmol) and 2,7-bistrimethyltin-4,5-dioctylbenzo[2,1-b:3,4-b']dithiophene (0.37g, 0.5mmol) in chlorobenzene (25mL) solution bubbling 0.5h removes residual oxygen, then adds 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.

[0057]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 chromatography, rinse with chloroform, remove...

Embodiment 3

[0058] Example 3 Preparation of Conjugated Polymer Containing Benzozodithiophene-Naphthalene Tetracarboxylic Diimide (n=60, x=1, y=1)

[0059]

[0060] Under argon protection condition, to containing compound N, N'-bis-(1-octylnonyl)-2,6-dibromo-1,4,5,8-naphthalene tetracarboxylic diimide (0.45 g, 0.5mmol) and 2,7-bistrimethyltin-4-methyl-5-n-eicosylbenzazole[2,1-b:3,4-b']dithiophene (0.41g, 0.5mmol) of chlorobenzene (25mL) solution was bubbled for 0.5h to remove residual oxygen, and then added Pd 2 (dba) 3 (0.014g, 0.015mmol) and P(o-Tol) 3 (0.0083g, 0.027mmol), and bubbled for 1h to remove residual oxygen. Then heated to 80 ° C reflux reaction for 48h.

[0061] 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 [2,1-b:3,4-b'] 2,2'-bithienyl-naphthalene diimide-containing conjugated polymer, which is characterized by being a compound shown as a general formula in the specifications, wherein R1 and R2 refer to alkyl with 1-20 carbon atoms; R3 refers to alkyl with 1-20 carbon atoms or shown substituted phenyl; R4, R5 and R6 represent hydrogen and alkyl or alkoxyl with 1-20 carbon atoms likewise or differently; x is more than or equal to 1 and less than 2; y is more than 0 and less than or equal to 1; x+y=2; and an is an integer ranging from 1 to 120. The [2,1-b:3,4-b'] 2,2'-bithienyl-naphthalene diimide-containing conjugated polymer is prepared by undergoing a Stille reaction which has a simple reaction synthesis route and low process requirements, and has high film forming performance, high thermal stability performance, high carrier mobility, high molar absorptivity, a wide light absorbing range and wide application; and the matching degree with a sunlight emission spectrum is increased, and the photoelectric conversion efficiency can be increased.

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