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Organic small-molecular semiconductor material containing anthracene tetrathiophene and application of material

A small molecule and semiconductor technology, applied in the field of organic optoelectronics, can solve the problems of narrow absorption range in the visible light region, difficult preparation and purification, high raw material cost, and achieve the effects of strong chemical modifiability, good light capture ability, and high electron mobility.

Active Publication Date: 2018-05-08
东莞伏安光电科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Among them, fullerene and its derivatives (such as PC 61 BM and PC 71 The electron acceptor materials prepared by BM) have made a great contribution to the development of organic solar cells, but these materials also have their own defects, such as high cost of raw materials, difficulty in preparation and purification, narrow and weak absorption range in the visible light region, and poor compatibility with donors. Materials tend to aggregate when blended

Method used

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  • Organic small-molecular semiconductor material containing anthracene tetrathiophene and application of material
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  • Organic small-molecular semiconductor material containing anthracene tetrathiophene and application of material

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Embodiment 1

[0021] The synthesis of embodiment 1, compound 3, reaction formula is as follows:

[0022]

[0023] Take R as 2-ethylhexyl as an example for illustration.

[0024] Add compound 1 (4.87g, 10mmol), compound 2 (29.1g, 60mmol) and Pd(PPh 3 ) 4 (800 mg), add a stirring bar, pump and ventilate 3 times, take 100ml of toluene, join in the two-necked flask, then heat in an oil bath, react overnight at 100 ° C, the solution is brown. The product was washed with water first, then extracted with dichloromethane, dried over anhydrous magnesium sulfate, and passed through the column with petroleum ether eluent to obtain about 5.13 g of compound 3 with a yield of 60.0%.

Embodiment 2

[0025] The synthesis of embodiment 2, compound 4, reaction formula is as follows:

[0026]

[0027] Take R as 2-ethylhexyl as an example for illustration.

[0028] Add compound 3 (1.7g, 2mmol) into a 50mL single-necked bottle, add 25mL tetrahydrofuran and stir to dissolve it, and add N-bromosuccinimide (NBS) (1.6g, 8.8 mmol), and react in the dark for 12 hours at room temperature. Conventional CH 2 Cl 2 After the extraction treatment, the silica gel was separated and purified through a column, and petroleum ether was used to pass through a column to obtain the product compound 4 (2.1 g, yield 90%).

Embodiment 3

[0029] The synthesis of embodiment 3, compound 5, reaction formula is as follows:

[0030]

[0031] Take R as 2-ethylhexyl as an example for illustration.

[0032] Ferric chloride (1.3g, 8mmol) was dispersed in 200mL of dichloromethane, stirred for half an hour, then a solution of compound 4 (1.17g, 1mmol) in dichloromethane (20mL) was added dropwise to the system. After the dropwise addition was completed, 500 mL of methanol was added thereto after half an hour of reaction, and the crude product was obtained by filtration. The crude product was separated and purified with silica gel, and petroleum ether was used to pass through the column to obtain the product compound 5 (0.91 g, yield 78%).

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Abstract

The invention discloses an organic small-molecular semiconductor material containing anthracene tetrathiophene and application of the material. The structural formula of the material is the formula I(the formula can be seen in the description), wherein a unit A is an electron-deficient group, and R1 and R2 are hydrogen, or alkyl groups with 1-30 carbon atoms, or groups formed by substituting oneor more carbon atoms in the alkyl groups with 1-30 carbon atoms with halogen atoms, oxygen atoms, alkenyl groups, alkynyl groups, aryl groups, hydroxyl groups, amino groups, carbonyl groups, carboxylgroups, ester groups, cyano groups or nitryl groups. The material has four active sites, can be connected with four electron withdrawing groups, and is high in chemical modification property; the organic semiconductor material has good light capturing capacity, is beneficial for obtaining high electronic mobility due to the large conjugate plane, and can be used as an electron acceptor material inthe field of organic battery devices. The material is used as the electron acceptor material in organic solar battery devices, and good device performance is obtained.

Description

technical field [0001] The invention belongs to the field of organic photoelectric technology, and in particular relates to a preparation method of a high-performance organic small molecule semiconductor material and its application in organic photoelectric devices. Background technique [0002] Organic solar cells (OSCs) are currently one of the hotspots in the field of new materials and new energy. Area preparation of flexible devices and other advantages. Among them, fullerene and its derivatives (such as PC 61 BM and PC 71 The electron acceptor materials prepared by BM) have made a great contribution to the development of organic solar cells, but these materials also have their own defects, such as high cost of raw materials, difficulty in preparation and purification, narrow and weak absorption range in the visible light region, and poor compatibility with donors. Materials tend to aggregate when blended. Therefore, designing and synthesizing new non-fullerene accep...

Claims

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Application Information

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IPC IPC(8): C07D495/22H01L51/50H01L51/54
CPCC07D495/22H10K85/615H10K85/6576H10K50/00Y02E10/549
Inventor 黄飞谢锐浩应磊曹镛
Owner 东莞伏安光电科技有限公司
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