Thienothiophene quinone-type organic photoelectric material, its preparation method and application

A technology of organic optoelectronic materials and thiophene quinoids, which can be used in light-emitting materials, chemical instruments and methods, circuits, etc., and can solve problems such as low photoelectric conversion efficiency.

Inactive Publication Date: 2011-12-14
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 orga...

Method used

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  • Thienothiophene quinone-type organic photoelectric material, its preparation method and application
  • Thienothiophene quinone-type organic photoelectric material, its preparation method and application
  • Thienothiophene quinone-type organic photoelectric material, its preparation method and application

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preparation example Construction

[0032] see figure 2 , the preparation method of the above-mentioned thienothiophene quinone type organic photoelectric material comprises the following steps:

[0033] S10, selecting compounds A, B, and C: that is, selecting compounds A, B, and C represented by the following structural formula,

[0034] Where: R 1 , R 2 , R 3 , R 4 , R 5 , R 6 Choose from H, C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy; m, n are integers of 0-10;

[0035] S20, generation of dibromo product: dissolving compound C and alkyllithium in an organic solvent, then adding trialkyltin chloride, stirring and reacting to generate compound C substituted by alkyltin, and then under the conditions of catalyst and organic solvent , select compound A, B and compound C substituted by alkyltin to carry out Stille coupling reaction, then carry out bromination substitution reaction between Stille coupling reaction product and brominating agent, generate dibrominated product; or carry out bromination of compou...

Embodiment 1

[0078] The thienothiophene quinone type organic semiconductor material of the present embodiment (I 1 ), m=n=0, R 3 , R 4 Both are H, and its structural formula is as follows:

[0079]

[0080] The preparation of the above-mentioned thienothiophene quinone-type organic semiconductor material is described in the above-mentioned case of m=n=0, and the following specific steps are adopted in this embodiment:

[0081] One, prepare the dibromo product 2 of compound C, 5-dibromo-thieno[3,2-b]thiophene, the specific structural formula of the dibromo product in the present embodiment is as follows:

[0082]

[0083] The specific preparation process is as follows: Add thieno[3,2-b]thiophene (unsubstituted compound C) and NBS to tetrahydrofuran at a molar ratio of 1.0:2.0 at -5°C to 30°C, and react for 12 to 48 hours , to obtain the product, namely the dibromo product of the above structural formula. After the reaction was completed, the reaction solution was poured into ice w...

Embodiment 2

[0087] The thienothiophene quinone type organic semiconductor material of the present embodiment (I 2 ), m=n=1, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 Both are H, and its structural formula is as follows:

[0088]

[0089] The preparation steps of the above-mentioned thienothiophene quinone type organic semiconductor material are as follows:

[0090] One, the preparation of 2,5-bis(trimethyltin)thieno[3,2-b]thiophene, its structural formula is as follows:

[0091]

[0092] The preparation process is as follows: add 2.80 g of thieno[3,2-b]thiophene and 80.0 mL of anhydrous THF solution, and add 40.00 mL of n-butyllithium solution (concentration: 2.00 mol / L, at In n-hexane solution), after stirring for 2 hours, add 15.99g of trimethyl tin chloride, continue to stir for 24 hours. After the reaction was completed, the reaction liquid was returned to room temperature, and saturated ammonium chloride aqueous solution was added, extracted with ether, dried over anhydrous mag...

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Abstract

The invention relates to the technical field of organic materials and provides a thienothiophene quinoid organic photoelectric material. The material is a compound which is shown as a structural formula (I); in the formula, R1, R2, R3, R4, R5 and R6 are selected from H, C1-C20 alkyl group or C1-C20 alkoxyl group; and m and n are integers of 0-10. The invention also provides a preparation method and application of the thienothiophene quinoid organic photoelectric material. Since the thienothiophene quinoid organic photoelectric material has a quinoid thiophene ring and a cyano group, wider spectral response is guaranteed, the photoelectric conversion efficiency of the material is increased, and better thermal stability and environmental stability are shown.

Description

technical field [0001] The invention belongs to the technical field of organic materials, and in particular relates to a thienothiophene quinone type organic photoelectric material, its preparation method and application. Background technique [0002] Today's world economy is mainly based on fossil energy, such as coal, oil and natural gas. However, these non-renewable fossil energy sources are constantly being exhausted. Since the beginning of the 21st century, global energy issues and the ensuing environmental pollution and climate warming have become increasingly prominent and gradually intensified. Solar energy is considered to be one of the most promising renewable energy sources because of its widespread and vast distribution, large amount of resources, no pollution, cleanliness, safety, and easy access. [0003] In order to make full use of the energy irradiated by sunlight, people continue to develop new materials that can absorb sunlight. Among them, inorganic sem...

Claims

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Application Information

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IPC IPC(8): C08G61/12C09K11/06H01L51/00H01S5/36
Inventor 周明杰黄杰刘辉
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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