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Perylenetetracarboxylic acid diimide copolymer containing bisthienopyrrole unit and its preparation method and application

A technology of perylene tetracarboxylic acid diimide copolymer and perylene tetracarboxylic acid diimide, which is applied in the fields of electrical components, semiconductor/solid-state device manufacturing, and electric solid-state devices, etc., can solve the problem that the devices are prone to phase separation and dissolution. It can solve the problems of poor performance, poor film-forming processing performance, etc., to achieve the effects of excellent charge transport performance, wide absorption range and low equipment requirements.

Inactive Publication Date: 2011-12-14
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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 Its solubility is poor, and its film-forming performance is poor, 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 acid diimide copolymer containing bisthienopyrrole unit and its preparation method and application
  • Perylenetetracarboxylic acid diimide copolymer containing bisthienopyrrole unit and its preparation method and application
  • Perylenetetracarboxylic acid diimide copolymer containing bisthienopyrrole unit and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1 Poly N, N'-bis-(3,4,5-tri-methylbenzene)-3,4,9,10-perylenediimide-N-hexylbisthieno[3,2- b: 2′,3′-d]pyrrole:

[0044]

[0045] 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 mmol, 2,6-bistrimethyltin-N-hexylbisthieno[3,2-b:2′,3′-d]pyrrole 0.5mmol in DMF (18mL) solution was bubbled for 0.5h to remove residual Oxygen; then add Pd 2 (dba) 3 (0.0.14g, 0.015mol) and P(o-Tol) 3 (0.0083g, 0.027mmol) and bubbling for 0.5h to remove residual oxygen, and then heated to 80 ° C for 48 hours; the reaction mixture was added dropwise to methanol for sedimentation treatment, then suction filtered, washed with methanol, and dried , to obtain the heteropolymer colloid; then dissolve it with toluene to obtain the toluene solution of the copolymer; then, add the toluene solution to the aqueous solution of sodium diethyldithiocarbamate, heat and stir the mixed solution at 90°C, and dissolve the m...

Embodiment 2

[0046] Example 2 Poly N, N'-bis-(3,4,5-tri-methoxybenzene)-3,4,9,10-perylenediimide-N-octylbisthieno[3, 2-b: 2',3'-d]pyrrole:

[0047]

[0048] Under the protection of nitrogen, to the compound N,N'-bis-(3,4,5-tri-methoxybenzene)-1,7-dibromo-3,4,9,10-perylene diimide 0.5mmol, 0.5mmol of 2,6-bistrimethyltin-N-octylbithieno[3,2-b:2′,3′-d]pyrrole in dioxane (15mL) solution was bubbled 0.5h to remove residual oxygen; then add Pd(PPh 3 ) 2 Cl 2 10mg, and bubbling for 0.5h to remove residual oxygen, and then heated to 85°C for 36 hours; the reaction mixture was added dropwise into methanol, settled, then suction filtered, washed with methanol, and dried to obtain a heteropolymer Colloid; then dissolved in toluene to obtain the toluene solution of the copolymer; then, add the toluene solution to the aqueous solution of sodium diethyldithiocarbamate, heat and stir the mixed solution at 90°C, and pass the mixed solution through the column of alumina Chromatography, isolate the...

Embodiment 3

[0049] Example 3 Poly N, N'-bis-(3,4,5-tri-octyloxybenzene)-3,4,9,10-perylene diimide-N-eicosylbisthieno[ 3,2-b:2′,3′-d]pyrrole:

[0050]

[0051] Under the protection of nitrogen, to the compound N, N'-bis-(3,4,5-tri-octyloxybenzene)-1,7-dibromo-3,4,9,10-perylene diimide Bubble 0.5mmol of 0.5mmol, 2,6-bistributyltin-N-eicosylbisthieno[3,2-b:2′,3′-d]pyrrole in toluene / THF (30mL) solution h to remove residual oxygen; then add Pd(PPh 3 ) 4 8mg and bubbling for 0.5h to remove residual oxygen, and then heated to 80°C for 72 hours; the reaction mixture was added dropwise to methanol for sedimentation treatment, then suction filtered, washed with methanol, and dried to obtain a heteropolymer colloid; then dissolved in toluene to obtain the toluene solution of the copolymer; then, add the toluene solution to the aqueous solution of sodium diethyldithiocarbamate, heat and stir the mixed solution at 80°C, and pass the mixed solution through the column layer of alumina The copol...

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Abstract

The invention relates to a perylene tetracarboxylic diimide copolymer containing a dithiophen-pyrrole unit and a preparation method and application thereof. The structural formula of the copolymer is shown in the specification, wherein n is an integer between 1 and 100; R1, R2 and R3 are hydrogen, C1-C20 alkyl, C1-C20 alkoxy benzene or phenyl; and R4 is C1-C20 alkyl. By introducing a substituent to a 'bay' position of perylene tetracarboxylic diimide and copolymerizing the perylene tetracarboxylic diimide with other monomers, the solubility of the perylene tetracarboxylic diimide can be effectively improved; and the modified perylene tetracarboxylic diimide has good solubility, strong absorbance, wide absorption range, improved utilization rate of sunlight and excellent charge transport properties, can extend to a near-infrared region, and can be used as an organic semiconductor material to be applied in organic solar cells, organic electroluminescence, organic field-effect transistors, organic optical storage, organic non-linear materials, organic lasers and other fields.

Description

【Technical field】 [0001] The invention relates to a conjugated polymer, in particular to a perylene tetracarboxylic diimide copolymer containing bisthienopyrrole units, a preparation method and application thereof. 【Background technique】 [0002] The preparation of low-cost and high-efficiency solar cells using cheap materials has always been a hot and difficult point in the field of photovoltaic research. Traditional silicon solar cells for ground applications are limited 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. Since 1992, N.S.Sariciftci et al reported on SCIENCE (N.S Sariciftci, L.Smilowitz, A.J.Heeger, et al.Science, 1992,...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/54H01L51/30
CPCH01L51/0053Y02E10/549H10K85/621
Inventor 周明杰黄杰管榕
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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