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Naphthalene tetracarboxylic diimide-naphtho dithiophene-containing copolymer and preparation method as well as application thereof

A technology containing naphthalene tetracarboxylic acid diimide and naphthalene tetracarboxylic acid diimide, which is applied in the structure of active regions, semiconductor/solid-state device manufacturing, and electric solid-state devices, and can solve the problem of insufficient matching of emission spectra High, unable to effectively use sunlight, poor solubility of naphthalimide, etc., to achieve good solubility, excellent charge transport performance, and strong absorbance

Inactive Publication Date: 2012-12-26
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

[0005] The technical problem to be solved by the present invention is that in the prior art, naphthalimide and its derivatives have poor solubility and poor film-forming processability, and their emission spectrum matching with sunlight is not high enough to be effective. To make full use of the defects of sunlight to provide a perylene tetracarboxylic diimide copolymer containing naphthodithiophene units with good solubility and strong absorbance. The absorption range of the copolymer can be extended to the near infrared region, which can improve the solar light utilization

Method used

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  • Naphthalene tetracarboxylic diimide-naphtho dithiophene-containing copolymer and preparation method as well as application thereof
  • Naphthalene tetracarboxylic diimide-naphtho dithiophene-containing copolymer and preparation method as well as application thereof
  • Naphthalene tetracarboxylic diimide-naphtho dithiophene-containing copolymer and preparation method as well as application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1 Poly N, N'-bis-(2-octyldecyl)-1,4,5,8-naphthalene diimide-(5-methyl-6-methoxy)naphtho[2 , Preparation of 1-b:3,4-b']dithiophene (n=30):

[0038]

[0039] Under nitrogen protection conditions, for containing N, N'-bis-(2-octyldecyl)-2,6-dibromo-1,4,5,8-naphthalene diimide (0.5mmol) and 2 , 9-bistributyltin-(5-methyl-6-methoxy)naphtho[2,1-b:3,4-b']dithiophene (0.5mmol) DMF (18mL) solution bubbled 0.5 h to remove residual oxygen, then add Pd 2 (dba) 3 (0.014g, 0.015mmol) and P(o-Tol) 3 (0.0083g, 0.027mmol), and bubbled for 0.5h to remove residual oxygen, and then heated to 80°C for 48h in an oxygen-free atmosphere.

[0040] Add the reaction mixture dropwise to methanol for sedimentation, and dissolve it with toluene after suction filtration, methanol washing and drying steps, add it to the aqueous solution of sodium diethyldithiocarbamate, heat to 90°C and stir for 6-16h. Pass the organic phase through column chromatography of alumina, rinse with chlorobe...

Embodiment 2

[0041] Example 2 Poly N, N'-bis-(2-hexyloctyl)-1,4,5,8-naphthalene diimide-(5-hexyl-6-decyl)naphtho[2,1- b: Preparation of 3,4-b']dithiophene (n=22):

[0042]

[0043] Under nitrogen protection condition, to containing compound N, N'-bis-(2-hexyloctyl)-2,6-dibromo-1,4,5,8-naphthalene diimide (0.5mmol) and 2 , a solution of 9-bistributyltin-(5-hexyl-6-decyl)naphtho[2,1-b:3,4-b']dithiophene (0.5 mmol) in dioxane (15 mL) 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 36h in an oxygen-free atmosphere.

[0044] Add the reaction mixture dropwise to methanol for sedimentation, and dissolve it with toluene after suction filtration, methanol washing and drying steps, add it to the aqueous solution of sodium diethyldithiocarbamate, heat to 90°C and stir for 6-16h. Pass the organic phase through column chromatography of alumina, rinse with chlorobenzene, remove the organic...

Embodiment 3

[0045] Example 3 Poly N, N'-bis-(2-methyltetradecyl)-1,4,5,8-naphthalene diimide-(5,6-di-eicosyl)naphtho Preparation of [2,1-b:3,4-b']dithiophene (n=16):

[0046]

[0047] Under the condition of nitrogen protection, for the compound containing N, N'-bis-(2-methyltetradecyl)-2,6-dibromo-1,4,5,8-naphthalene diimide (0.5mmol ) and 2,9-bistributyltin-(5,6-di-eicosyl)naphtho[2,1-b:3,4-b']dithiophene (0.5mmol) in toluene / THF (30mL ) solution was bubbled for 0.5h to remove residual oxygen, then added Pd(PPh 3 ) 4 (8mg), and bubbling for 0.5h to remove residual oxygen, and then heated to 80°C for 72h in an oxygen-free atmosphere.

[0048] Add the reaction mixture dropwise to methanol for sedimentation, and dissolve it with toluene after suction filtration, methanol washing and drying steps, add it to the aqueous solution of sodium diethyldithiocarbamate, heat to 80°C and stir for 6-16h. Pass the organic phase through column chromatography of alumina, rinse with chlorobenzene, r...

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Abstract

The invention discloses naphthalene tetracarboxylic diimide-naphtho dithiophene-containing copolymer and a preparation method as well as application thereof. The polymer is a compound which has a general formula shown in the specification, wherein R1 and R2 are selected from H, C1-C20 alkyl groups, phenyl groups or substituted phenyl groups with C1-C20 alkoxyl groups; R3 and R4 are selected form C1-C20 alkyl groups or alkoxyl groups; and n is an integer of 1-100. The naphthalene tetracarboxylic diimide-naphtho dithiophene-containing copolymer is prepared through Stille reaction with a simple reaction synthesis route and low technological requirements, and has the characteristics of high dissolubility, strong absorbency, superior charge transfer performance, capability of extending an absorption range to a near infrared region, capability of increasing utilization rate of sunlight, wide application and the like.

Description

technical field [0001] The invention relates to the technical field of polymer materials, in particular to a polymer, its preparation method and its application, more specifically, to a copolymer containing naphthalene tetracarboxylic acid diimide-naphthodithiophene, its 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, printing, etc....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/00H01S5/36H10K99/00
Inventor 周明杰黄杰管榕
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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