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Organic small molecular semiconductor material containing anthracene dithiophene as well as preparation method and application thereof

A bithiophene and semiconductor technology, applied in the field of organic optoelectronics, can solve the problems of high cost of raw materials, easy aggregation, difficulty in preparation and purification, etc., and achieve the effects of good device performance, high electron mobility, and good light harvesting ability

Active Publication Date: 2018-06-05
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 dithiophene as well as preparation method and application thereof
  • Organic small molecular semiconductor material containing anthracene dithiophene as well as preparation method and application thereof
  • Organic small molecular semiconductor material containing anthracene dithiophene as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1、1

[0028] Embodiment 1, the synthesis of 1,4-dibromo-2,5-diiodobenzene

[0029]

[0030] Add 1,4-dibromobenzene (10.00g, 42.39mmol) and simple iodine (43.04g, 169.56mmol) into a 500ml one-necked flask, and slowly add 200ml of concentrated sulfuric acid at room temperature. Install a spherical condenser on the top of the single-necked flask, heat the flask in an oil bath at 125°C, turn on the condensed water, make it reflux, and react like this for 3 days. The color of the solution gradually changed from initial purple to dark purple to black. The final product was white mixed with black, and the solution was black. Take a 1000ml large beaker, add a large amount of ice cubes, slowly pour the reaction solution into it, stir to cool it down, filter it with a suction filter, and use NaHCO 3 and Na 2 S 2 o 3 The solution was washed repeatedly to remove I 2 , the suction filtration device sucked the filter residue, heated and dissolved the filter residue with DCM, filtered and...

Embodiment 2

[0032] Embodiment 2, the synthesis of 2-(4-bromothien-2-yl)-1,3-dioxolane

[0033]

[0034] Add 4-bromothiophene-2-carbaldehyde (5g, 26.17mmol), ethylene glycol (3.25g, 52.35mmol), 200mg of p-toluenesulfonic acid as a catalyst, and 100ml of toluene as a solvent in a single-necked flask. The water tank removes the water generated by the reaction. Through condensed water, heated to reflux for 8h. After the reaction was completed, p-toluenesulfonic acid was removed with NaOH solution, extracted, and the upper layer was the desired product. Then pass through the column, the collected sample solution is light yellow, 6.10 g, and the yield is 99.2%.

[0035] 1 H NMR (500MHz, CDCl3) δ7.20(s,1H),7.00(s,1H),5.58(s,1H),3.35(s,4H).

Embodiment 3

[0036] Embodiment 3, the synthesis of (3-bromo-5-(1,3-dioxolan-2-yl) thiophen-2-yl) tributylstannane

[0037]

[0038] Add 2-(4-bromothiophen-2-yl)-1,3-dioxolane (3.68g, 15.65mmol) into a two-necked flask, pump and ventilate 3 times, use a 50ml syringe to extract 20ml of anhydrous THF, Pour into a two-necked flask. Allow it to stir at -20°C for 10 minutes, ventilate, take 17.22ml (17.22mmol) LDA with a long needle, and add it dropwise in a two-necked flask. The color of the solution changes from light yellow to reddish brown, then dark red, and finally turns black. Allow it to react at -20°C for 2 hours, then take 4.56ml (1.118g / ml) tributyltin chloride into the reaction solution with a long needle, return to normal temperature, and react overnight to obtain a light yellow transparent viscous liquid. Extracted 3 times with n-hexane, washed 3 times with NaCl aqueous solution, filtered and rotary evaporated to remove the solvent, and then dried the solvent with a diaphragm ...

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Abstract

The invention discloses an organic small molecular semiconductor material containing anthracene dithiophene as well as a preparation method and an application thereof. The structural formula of the material is as shown in a formula I, wherein the unit A is an electron deficient group; R1 is hydrogen or alkyl with 1-30 carbon atoms or a group in the alkyl with 1-30 carbon atoms, one or more of which are replaced by halogen atoms, oxygen atoms, alkenyl, alkynyl, aryl, hydroxyl, amino, carboxyl, ester groups, cyan or nitryl. The material has unique advantages of relatively good light capturing ability, proper electronic energy level, relatively high electronic mobility and the like, and is applied to organic solar battery apparatuses as an electron acceptor material to obtain good apparatus performances.

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): C07D495/04H01L51/46H01L51/42
CPCC07D495/04H10K85/6565H10K85/6576H10K30/30Y02E10/549Y02P20/55
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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