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Fused ring thiophene organic photoelectric material and preparation methods and application thereof

A technology of organic optoelectronic materials and fused ring thiophene, which can be applied in the fields of luminescent materials, organic chemistry, photovoltaic power generation, etc., can solve the problem of low photoelectric conversion efficiency, and achieve the effect of large conjugation and coplanarity

Inactive Publication Date: 2011-08-10
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

However, so far, the photoelectric conversion efficiency of organic solar cells is much lower than that of inorganic solar cells

Method used

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  • Fused ring thiophene organic photoelectric material and preparation methods and application thereof
  • Fused ring thiophene organic photoelectric material and preparation methods and application thereof
  • Fused ring thiophene organic photoelectric material and preparation methods and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Example 1, this example discloses a fused-ring thiophene organic photoelectric material 1, which has the following structure:

[0051]

[0052] The first preparation method of fused ring thiophene organic photoelectric material 1:

[0053] One, the preparation of 5'-hexyl-2,2'-dithiophene-4-carbaldehyde (structural formula is as follows):

[0054]

[0055] 120mL of anhydrous THF was added to the pressure tube, and 2-hexyl-5-tributyltinthiophene (5.10g, 26.70mmol) and 5-bromo-3-formaldehyde thiophene (13.62g, 28.00mmol) were added rapidly, and nitrogen gas to below the liquid level for 30 minutes, then add Pd 2 (dba) 3 (0.49g, 0.53mmol) and P(o-Tol) 3 (0.33g, 1.07mmol), heated to 80°C, and reacted overnight. After the reaction was completed, KF (30.0 mL, 1.00 M) solution was added, stirred for 40 minutes, saturated aqueous sodium chloride was added, extracted with ether, dried over anhydrous magnesium sulfate, filtered, and rotary evaporated. The product was o...

Embodiment 2

[0072] Embodiment 2, the second preparation method of fused-ring thiophene organic photoelectric material 1 (structural formula as in Example 1):

[0073]One, 2-(2-(3-formyl-5-(5-hexylthiophen-2-yl)thiophen-2-yl)thieno[3,2-b]thiophen-5-yl)-5-( Preparation of 5-hexylthiophen-2-yl)thiophene-3-carbaldehyde:

[0074]

[0075] 20mL THF was added to the pressure tube, and 5-bromo-5'-hexyl-2,2'-dithiophene-4-carbaldehyde (0.36g, 1.00mmol) and 2,5-bis(trimethyl Tin) thieno[3,2-b]thiophene (0.23g, 0.50mmol), nitrogen flow to below the liquid level for 20 minutes, then add Pd 2 (dba) 3 (0.0092g, 0.010mol) and P(o-Tol) 3 (0.0061g, 0.020mmol), heated to 85°C, and reacted overnight. After the reaction was completed, KF (14.0 mL, 1.00 M) solution was added, stirred for 20 minutes, saturated aqueous sodium chloride solution was added, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered, and rotary evaporated. Petroleum ether: using petroleum ether / dichlorom...

Embodiment 3

[0081] Example 3, the fused-ring thiophene organic photoelectric material 2 disclosed in this example has the following structure:

[0082]

[0083] The first preparation method of fused ring thiophene organic photoelectric material 2:

[0084] 1. Preparation of 5 "-octyl-2,2': 5', 2"-bithiophene-4-carbaldehyde (structural formula is as follows):

[0085]

[0086] Add 40 mL of anhydrous THF to a pressure-resistant tube, and quickly add tributyl(5'-octyl-2,2'-dithiophen-5-yl)tin (5.68 g, 10.00 mmol) and 5-bromo-3 -Formaldehyde-based thiophene (4.86g, 10.00mmol), nitrogen flow to below the liquid level for 30 minutes, then add Pd 2 (dba) 3 (0.18g, 0.20mmol) and P(o-Tol) 3 (0.13g, 0.40mmol), heated to 100°C, and reacted overnight. After the reaction was completed, KF (23.0 mL, 1.00 M) solution was added, stirred for 30 minutes, saturated aqueous sodium chloride was added, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered, and rotary evaporat...

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Abstract

The invention discloses a fused ring thiophene organic photoelectric material and preparation methods and application thereof. The material is a compound. A first preparation method of the fused ring thiophene organic photoelectric material comprises the following steps of: respectively performing a condensation reaction of two raw materials and malononitrile under the action of a catalyst; and performing a Stille coupling reaction of two condensation products and the other raw material under the catalysis of an organic palladium catalyst to obtain the fused ring thiophene organic photoelectric material. A second preparation method of the fused ring thiophene organic photoelectric material comprises the following steps of: performing the Stille coupling reaction under the catalysis of the organic palladium catalyst; and then performing the condensation reaction of a coupling product and the malononitrile to obtain the fused ring thiophene organic photoelectric material. The fused ring thiophene organic photoelectric material is applied to the manufacturing of organic solar cell devices, organic field effect transistors, organic electroluminescent devices and the like. The material can be well matched with an emission spectrum of sunlight and has high photoelectric conversion efficiency, better thermal stability and environment stability, simple preparation methods and low process requirements.

Description

technical field [0001] The invention relates to a polymer material, a preparation method and its application, in particular to a condensed ring thiophene organic photoelectric material, its preparation method and its application in organic solar cell devices, organic electroluminescent devices and organic field effect transistors. Background technique [0002] Solar energy is one of the most promising renewable energy sources due to its outstanding advantages such as widespread and vast distribution, large amount of resources, clean and pollution-free, safe and easy to obtain. Solar cells can directly convert sunlight energy into electrical energy, which is a feasible and effective way to utilize solar energy. However, currently commercialized solar cells are limited to silicon-based and other inorganic solar cells. Inorganic solar cells are too expensive, their popularity is limited, and their scope of use is also limited. In order to reduce the cost of solar cells and exp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D495/04H01L51/46H01L51/54H01L51/30G02F1/361
CPCY02E10/50Y02E10/549Y02P70/50
Inventor 周明杰黄杰刘辉
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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