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Perylenetetracarboxylic diimide copolymers, preparation method thereof and application thereof

A perylene tetracarboxylic acid diimide copolymer and a technology of perylene tetracarboxylic acid diimide, which are applied in the field of copolymers, can solve the problem of reducing the photoelectric conversion efficiency of organic solar cells, failing to effectively utilize sunlight, and matching emission spectra. Insufficient degree of light and other problems, to achieve the effect of excellent charge transport performance, wide range of light absorption, and excellent solubility

Active Publication Date: 2012-03-14
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since perylenetetracarboxylic acid diimide and its derivatives contain a large planar conjugated system and good molecular coplanarity, the interaction of large π bonds between molecules is very strong and has a large lattice energy, so It has poor solubility and poor film-forming processability, which leads to the phase separation problem of the prepared device, which affects the efficiency of exciton diffusion, resulting in energy loss
In addition, since the absorption spectrum of perylenetetracarboxylic diimide and its derivatives is mainly concentrated in the visible region, the absorption range is not wide enough, and the matching degree with the emission spectrum of sunlight is not high enough, so the sunlight cannot be effectively used, and the will reduce the photoelectric conversion efficiency of organic solar cells

Method used

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  • Perylenetetracarboxylic diimide copolymers, preparation method thereof and application thereof
  • Perylenetetracarboxylic diimide copolymers, preparation method thereof and application thereof
  • Perylenetetracarboxylic diimide copolymers, preparation method thereof and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0036] Poly N,N'-bis-(3,4,5-tri-methylbenzene)-3,4,9,10-perylenediimide-1,1,3,4-tetramethyl-2, 5-bisphenylsilole (n=9):

[0037]

[0038] Under the protection of nitrogen, to the compound N,N'-bis-(3,4,5-tri-methylbenzene)-1,7-dibromo-3,4,9,10-perylene diimide 0.5 A solution of 0.5 mmol of 1,1,3,4-tetramethyl-2,5-bis(4-tributyltin-phenyl)silole in N,N-dimethylformamide (18 mL). Nitrogen was introduced, and the residual oxygen was removed by bubbling for 0.5h. Then join Pd 2 (dba) 3 (0.014g, 0.015mmol) and P(o-Tol) 3 (0.0083g, 0.027mmol); continue to feed nitrogen, bubbling for 0.5h to remove residual oxygen, and then heated to 80°C for 48 hours to obtain poly N,N'-bis-(3,4,5-tri- Reaction mixture of methylbenzene)-3,4,9,10-perylenediimide-1,1,3,4-tetramethyl-2,5-bisphenylsilole (n=9) .

[0039] Add the reactant mixture dropwise to methanol for sedimentation, filter with suction, wash with methanol, and dry; then dissolve in toluene, add to the aqueous solution of sod...

Embodiment 2

[0041] Poly N,N'-bis-(3,5-dimethyloxy-4-dodecyloxybenzene)-3,4,9,10-perylenediimide-1,1-dioctyl- 3,4-diphenyl-2,5-bisphenylsilole (n=23):

[0042]

[0043] Under the protection of argon, to the compound N,N'-bis-(3,5-dimethyloxy-4-dodecyloxy)-1,7-dibromo-3,4,9,10- Perylene diimide 0.5mmol, 1,1-dioctyl-3,4-diphenyl-2,5-bis(4-tributyltin-phenyl)silole 0.5mmol of dioxane (15mL) solution. Introduce argon, bubble 0.5h to remove residual oxygen. Then add Pd(PPh 3 ) 2 Cl 2 10mg, continued to pass through argon, bubbled for 0.5h to remove residual oxygen, and then heated to 85 ° C for 36 hours to prepare poly N, N'-bis-(3,5-dimethyloxy-4-deca Dialkoxyphenyl)-3,4,9,10-perylenediimide-1,1-dioctyl-3,4-diphenyl-2,5-bisphenylsilole (n=23 ) reactant mixture.

[0044] The mixture was added dropwise to methanol for settling. Suction filtration, washing with methanol, and drying; then dissolved in toluene, added to the aqueous solution of sodium diethyldithiocarbamate; then the mi...

Embodiment 3

[0046] Poly N,N'-di-(3,4,5-tri-eicosyloxybenzene)-3,4,9,10-perylene diimide-1,1,3,4-tetra-di Decyl-2,5-bisphenylsilole (n=100):

[0047]

[0048] Under the protection of mixed gas of nitrogen and argon, to the compound N, N'-bis-(3,4,5-tri-eicosyloxybenzene)-1,7-dibromo-3,4,9, 0.5 mmol of 10-perylene diimide, 0.5 mmol of 1,1,3,4-tetra-eicosyl-2,5-bis(4-tributyltin-phenyl)silole 0.5 mmol in toluene / THF (30 mL) solution. A mixture of nitrogen and argon was introduced, and the residual oxygen was removed by bubbling for 0.5h. Then add Pd(PPh 3 ) 4 8mg, continue to pass through the mixed gas of nitrogen and argon, bubble 0.5h to remove the residual oxygen, and then heat to 80°C for 72 hours to prepare poly N,N'-bis-(3,4,5-tri-di Decyloxyphenyl)-3,4,9,10-perylenediimide-1,1,3,4-tetra-eicosyl-2,5-bisphenylsilole (n=100) reactant mixture.

[0049] The mixture was added dropwise to methanol for sedimentation, suction filtered, washed with methanol, and dried; then dissolved ...

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Abstract

The invention which belongs to the optoelectronic material field discloses perylenetetracarboxylic diimide copolymers. The perylenetetracarboxylic diimide copolymers have a structural formula represented by formula (I). In the formula (I), n is an integer between 1 and 100; R1, R2 and R3 are hydrogen, C1-C20 alkyl, C1-C20 alkoxy, phenyl, or alkoxybenzene; R4 is C1-C20 alkyl; and R5 is hydrogen, C1-C20 alkyl, C1-C20 alkoxy, or phenyl. The invention also provides a preparation method and an application of the perylenetetracarboxylic diimide copolymers. The diphenyl silole unit-contained perylenetetracarboxylic diimide copolymers have the advantages of good dissolving performance, high carrier mobility, strong absorbance, wide light absorption range, and sunlight utilization rate improvement; and the preparation method which has the advantages of simple process and high yield is easy to operate and control.

Description

technical field [0001] The present invention relates to a kind of copolymer, more specifically relates to a kind of perylene tetracarboxylic acid diimide copolymer. [0002] The invention also relates to a preparation method and application of a perylene tetracarboxylic acid diimide copolymer. Background technique [0003] 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 due to the advantages of low raw material prices, light weight, flexibility, simple production process, and large-area preparation by coating and printing. If the energy conversion effi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C09K11/06H01L51/46H01L51/54H01L51/30H01S5/36
CPCY02E10/549Y02P70/50
Inventor 周明杰黄杰管榕
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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