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Perylene diimide photoelectric functional materials and preparation method thereof

A photoelectric functional material, perylene imide technology, applied in the direction of photovoltaic power generation, circuits, electrical components, etc., can solve the problems of cost reduction of inorganic solar cells, photocorrosion limitations, etc., achieve good solubility, eliminate crystallization and pinholes, The effect of reducing production costs

Inactive Publication Date: 2011-05-25
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the total energy conversion efficiency of inorganic solar cells has reached more than 25%, the high cost and severe photocorrosion of narrow bandgap semiconductors limit the practical application of inorganic solar cells. Cost reduction is one of the main topics in this field

Method used

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  • Perylene diimide photoelectric functional materials and preparation method thereof
  • Perylene diimide photoelectric functional materials and preparation method thereof
  • Perylene diimide photoelectric functional materials and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1, N, N'-diisopropylbromophenylperylenediimide and 9,9'-dioctyl-2,7-dibromofluorene copolymer preparation:

[0042] (1) 2,2'-(9,9-di-n-octanefluorene-2,7-diyl)-bis([1,3,2]dioxaborinane)

[0043] Magnesium turnings (2.1 equiv.) and a little crystalline iodine were added to a 250 ml four-necked flask equipped with a reflux condenser and dropping funnel, which had been heat-dried and purged with nitrogen by evacuation. First, 1 ml of a solution of 2,7-dibromo-9,9-n-octanefluorene (1 equiv.) dissolved in tetrahydrofuran (10 ml) was added dropwise as quickly as possible, and the mixture was heated at the dropping site. After the reaction started, the remaining solution was slowly added dropwise, and the rate of addition was based on the automatic boiling of the reaction mixture. Tetrahydrofuran (ca. 1.10 ml) was then added and the mixture was refluxed for 2 h. The resulting clear Grignard solution was then cooled to room temperature and slowly added dropwise to an ...

Embodiment 2

[0046] Embodiment 2, the preparation of the copolymer of N, N'-dimethyl bromophthalic imide and 9-octyl-3,6-dibromocarbazole:

[0047] (1) Catalyst Ni(COD) 2 preparation of

[0048] Dissolve nickel 1,5-bicyclooctadienide, 1,5-cyclooctadiene and 2,2-bipyridine in dry toluene (3ml) and DMF (3ml) at a molar ratio of 1:1:1 In the mixed solution, replace N 2 , heated at 80°C for 30 minutes with stirring to prepare nickel catalyst

[0049] (2) Preparation of copolymer

[0050] A nickel catalyst (3 equiv.) was added to a 25ml two-necked flask equipped with a reflux condenser, the flask had been heated and dried and nitrogen was vented with vacuum. Add peryleneimide (1equiv.) and 9-octyl-3,6-dibromocarbazole (1equiv.) dissolved in 4ml toluene, heat at 80°C for 12h, add excess bromobenzene and keep heating for 1h, cool down The reactant was poured into a mixed solution of 400ml of toluene and hydrochloric acid (1:1) and stirred for 4 hours, filtered, and the precipitate was purifi...

Embodiment 3

[0051] Embodiment 3, N, the preparation of the copolymer of N'-dimethoxy bromophthalic imide and tertiary thiophene:

[0052] (1) Preparation of triple thiophene tin reagent

[0053] Prepare a dry and clean 25ml two-necked flask, replace the nitrogen, add the THF solution of dibromoterthiophene at -78 degrees, slowly add butyllithium, stir at room temperature for 1 hour, then cool to -78 degrees, slowly add tributyltin chloride The THF solution was stirred at room temperature for 4 hours. After the reaction, the mixture was poured into water, extracted, the organic phase was dried, spin-dried and passed through the column, and purified by recrystallization to obtain a pure triple thiophene tin reagent.

[0054] (2) Preparation of polymer

[0055] Put peryleneimide (1equiv), tertiary thiophene tin reagent (1equiv), tetrakistriphenylphosphorous palladium catalyst (0.02equiv) into a clean dry reaction test tube, add toluene and potassium carbonate saturated solution, under nitro...

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Abstract

The invention discloses perylene diimide-based photoelectric functional materials and a preparation method thereof. A series of polymers with different contents are prepared through Suzuki polymerization, Yamamoto polymerization, Stille polymerization or Sonogashira polymerization. The materials have good thermal, photic and chemical stability and good application prospects in the fields such as organic solar cells and the like. The structural formula of the perylene diimide-based polymers is shown in the specification, wherein a is a number between 1 and 30; b is a number between 0 and 30; R is C1-C10 alkyl or alkoxy; A1 is any one of the following structures shown in the specification, wherein n is a number between 1 and 10; and R is C1-C10 alkyl.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials. It specifically relates to a preparation method of a perylene imide polymer material, and relates to the application of this type of material in the field of organic solar cells. technical background [0002] A solar cell is a device that converts light energy (sunlight energy) into electricity. It is a photovoltaic device that was first discovered at Bell Laboratories in 1954. The initial research mainly focused on inorganic solar cells with single crystal silicon as the active material, and the device efficiency reported by Bell Labs at that time was 4%. Inorganic solar cells are usually based on a p-n junction structure: there are excess holes in the p region and excess electrons in the n region. Near the p-n junction, a built-in electric field is formed due to the sudden change of p-type and n-type. The electron-hole pairs generated after the material absorbs light, through ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C07D471/06C07D519/00H01L51/54H01L51/30H01L51/46
CPCY02E10/50Y02E10/549Y02P70/50
Inventor 陈润锋马琮黄维安众福张胜兰
Owner NANJING UNIV OF POSTS & TELECOMM
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