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Thiophene condensed 2,1,3-benzoxadiazole derivative and polymer thereof

A technology of benzodiazole and derivatives, which is applied in the field of polymers and optoelectronic materials, can solve the problems of low photoelectric conversion efficiency of organic solar cells, and achieve good thermal stability

Active Publication Date: 2015-07-15
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, compared with inorganic materials, the photoelectric conversion efficiency of organic solar cells is still low

Method used

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  • Thiophene condensed 2,1,3-benzoxadiazole derivative and polymer thereof
  • Thiophene condensed 2,1,3-benzoxadiazole derivative and polymer thereof
  • Thiophene condensed 2,1,3-benzoxadiazole derivative and polymer thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1: 4,8-bis-(5-bromothiophen-2 base)-2,1,3-benzothiadiazolo[4,5-b]thiophene-6-carboxylic acid-(2-ethane Synthesis of (ylhexyl) ester

[0045] The synthetic route is as follows:

[0046]

[0047] The synthesis method is:

[0048] Step 1: Preparation of N-(4-bromo-5-methyl-2-nitrophenyl)acetamide (2):

[0049]2-Nitro-5-methylaniline (1) (10.0 g, 65.7 mmol) and NBS (11.5 g, 64.6 mmol) were added to a 500 mL round bottom flask, and then 250 mL of glacial acetic acid was added. After the reactant was refluxed for 1.5 h, 10 ml of acetic anhydride was added thereto, and the reflux was continued for 4 h. After the reaction was completed, it was cooled to room temperature, and the mixture was poured into ice water to obtain a water-insoluble precipitate, which was filtered and washed three times with water, and the obtained product was After drying, 17.0 g of light yellow solid powder was obtained, with a yield of 99.7%. 1 H-NMR (300MHz, CDCl 3 ,δppm): 10.31(s,1H)...

Embodiment 2

[0062] Example 2: 4,8-bis-(5-bromothiophen-2 base)-2,1,3-benzoselenodiazolo[4,5-b]thiophene-6-carboxylic acid-(2-ethane Synthesis of (ylhexyl) ester

[0063] The synthetic route is as follows:

[0064]

[0065] The synthesis method is:

[0066] Step 1: Preparation of isooctyl 5-amino-6-nitrobenzo[4,5-b]thiophene-2-carboxylate:

[0067] Using 2-nitro-5-methylaniline as a raw material, 5-amino-6-nitrobenzo[4,5-b]thiophene-2-carboxylic acid isooctyl was synthesized according to the method of Example 1.

[0068] Step 2: Preparation of 4,8-dibromo-2,1,3-benzoselenodiazolo[4,5-b]thiophene-6-carboxylate-(2-ethylhexyl)ester (9):

[0069] In a 100 mL round bottom flask was added 5-amino-6-nitrobenzo[4,5-b]thiophene-2-carboxylate isooctyl (5) (0.40 g, 0.84 mmol) and SnCl 2 ﹒ 2H 2 O (0.48 g, 2.1 mmol), and then 10 mL of ethyl acetate was added. After reflux overnight, cool to room temperature, pour the reaction liquid into water, and extract and separate the liquids with ethyl ac...

Embodiment 3

[0074] Example 3: 4,8-bis-(5-bromothien-2yl)-2,1,3-benzothiadiazolo[4,5-b]thiophene-6-carboxylic acid-(2-butane Synthesis of octyl) esters

[0075] Synthetic route one:

[0076]

[0077] Synthetic route two:

[0078]

[0079] Synthetic route-corresponding method:

[0080] Step 1: Preparation of 5-amino-2-bromo-4-nitrobenzaldehyde:

[0081] Taking 2-nitro-5-methylaniline as raw material, synthesized according to the method of Example 1 to obtain 5-amino-2-bromo-4-nitrobenzaldehyde

[0082] Step 2: Preparation of ethyl 5-amino-6-nitrobenzo[4,5-b]thiophene-2-carboxylate (12):

[0083] Using 5-amino-2-bromo-4-nitrobenzaldehyde and ethyl thioglycolate as raw materials, synthesized according to the method of Example 1 to obtain 5-amino-6-nitrobenzo[4,5-b]thiophene- 2-Carboxylic acid ethyl ester, yield 99%. 1 H-NMR (300MHz, CDCl 3 ,δ): 8.67(s,1H), 7.81(s,1H), 7.25(s,1H), 5.84(s,2H), 4.42(q,2H), 1.42(t,3H).

[0084] Step 3: Preparation of ethyl 4,8-dibromo-2,1,3-benzothi...

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Abstract

The present invention provides a polymer with (Ⅱ) structured (II) structured after the two sides of the bridge is connected to the pyrenes of the pyrumone,Optical functional materials.The polymers formed by the new types of the present invention have good solubility and have a narrow band gap. It is an excellent photoelectric function material that can be used in the field of organic semiconductor photoelectricEssence

Description

technical field [0001] The invention relates to a thiophene-fused 2,1,3-benzodiazole derivative used for organic semiconductor materials and polymers formed with different donors after bridging thiophene on both sides, belonging to macromolecule and optoelectronics material field. Background technique [0002] Compared with inorganic materials, organic polymer optoelectronic functional materials have the advantages of light weight, low cost, easy cutting, and easy processing, etc., and large-area flexible devices can be conveniently prepared through solution process. Therefore, the synthesis of organic polymer materials with high photoelectric conversion efficiency and high charge mobility has attracted extensive attention in recent years. At present, people have obtained more than 10% photoelectric conversion efficiency through molecular tailoring and device optimization, (Jingbi You, Letian Dou, Ken Yoshimura, Takehito Kato, Kenichiro Ohya, Chun-Chao Chen, Jing Gao, Gang ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D513/04C07D517/04C08G61/12H01L51/46
CPCC07D513/04C07D517/04C08G61/123C08G61/126C08G2261/91C08G2261/414C08G2261/3246C08G2261/3243C08G2261/18H10K85/113H10K85/151Y02E10/549
Inventor 陈兴国周鹏程秦金贵
Owner WUHAN UNIV
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