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A-D-A type benzothiadiazole small molecule, preparation method and application thereof

A small benzothiadiazole, A-D-A technology, applied in the field of A-D-A type benzothiadiazole small molecules and their preparation, can solve the problems of high manufacturing cost, poor durability, disordered structure, etc.

Pending Publication Date: 2019-06-04
NANCHANG HANGKONG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In summary, the problems in the prior art are: the existing inorganic solar cells have the problems of high manufacturing cost and easy environmental pollution.
[0005] The difficulty of solving the above technical problems: organic solar cells have disadvantages such as low carrier mobility, disordered structure and poor durability, low energy conversion rate and short life of the battery

Method used

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  • A-D-A type benzothiadiazole small molecule, preparation method and application thereof
  • A-D-A type benzothiadiazole small molecule, preparation method and application thereof
  • A-D-A type benzothiadiazole small molecule, preparation method and application thereof

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preparation example Construction

[0046] The preparation method of the A-D-A type benzothiadiazole small molecule provided in the embodiment of the present invention includes:

[0047] S101: Preparation of reaction raw materials and reaction conditions; the reaction raw materials are: benzothiadiazoles with different numbers of fluorine (structural formulas are shown in formulas IV, V, and VI), electron-donating monomers, and catalysts;

[0048] S102: In an organic solvent system, under the protection of an inert gas, conduct a reaction in the dark;

[0049] S103: column chromatography purification;

[0050] S104: preparing the target product.

[0051] As a preferred embodiment of the present invention, step S101 specifically includes: the preparation method of the A-D-A type benzothiadiazole small molecule is specifically: from benzothiadiazoles with different numbers of fluorine (structural formulas such as formulas IV, V, Ⅵ) respectively react with electron-donating monomers and catalysts in an organic so...

Embodiment 1

[0071] The present invention provides a small molecule of A-D-A benzothiadiazole, the structural formula of which is formula I, as follows:

[0072]

[0073] The A-D-A type benzothiadiazole small molecular formula I provided in this example is prepared by the following method:

[0074]1 mol of the compound shown in formula IV and 0.5 mol (4,8-bis(octyloxy)benzo[1,2-B:4,5-B']dithiophene-2,6-diyl)di (Tributyltin) is placed in a toluene solvent, using tris(2-methylphenyl)phosphine as a catalyst, under the protection of an inert gas, the temperature is controlled at 110°C, the reaction is protected from light for 72 hours, and the target product formula I is obtained by column chromatography purification ; 1H NMR (CDCl3, 400MHz, δ / ppm): 8.03(d, 4H), 7.81(s, 4H), 7.63(s, 2H), 7.08(s, 2H), 4.41(t, 4H), 3.02( t, 4H), 2.75(, 4H), 1.75-2.35(m, 10H), 1.4-1.75(m, 34H), 0.75-1.75(m, 30H); 13CNMR(CDCl3, 100MHz, δ / ppm): 154.44 . The synthetic route of described formula I is as follows...

Embodiment 2

[0082] The present invention provides a small molecule of A-D-A benzothiadiazole, the structural formula of which is formula II, as shown below:

[0083]

[0084] The A-D-A type benzothiadiazole small molecular formula II provided in this example is prepared by the following method: 1 mol of the compound shown in formula V and 0.5 mol (4,8-bis(octyloxy)benzo[1,2 -B: 4,5-B']dithiophene-2,6-diyl)bis(tributyltin) is placed in toluene solvent, copper oxide is used as catalyst, under the protection of inert gas, the temperature is controlled at 110°C, avoiding Light reaction for 72h, column chromatography purification to obtain the target product formula II; 1HNMR (CDCl3, 400MHz, δ / ppm): 8.23 ​​(s, 4H), 7.85 (s, H), 7.75 (s, 3H), 7.53 (s, 3H), 4.26(t,4H), 2.91(t,4H), 2.63(t,4H), 1.51-2.25(m,22H), 0.75-1.51(m,52H); 13CNMR(CDCl3,100MHz,δ / ppm): 156.43, 146.86, 145.27, 141.11, 138.76, 137.72, 134.02, 132.25, 129.11, 127.88, 123.56, 117.27, 77.15, 35.98, 34.65, 32.41, 28.66, 24.131...

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Abstract

The invention belongs to the technical field of heterocyclic compounds, and discloses an A-D-A type benzothiadiazole small molecule, a preparation method and application thereof. The preparation method comprises: first, under the condition of shielding from light, respectively reacting benzothiadiazoles with different numbers of fluorine atoms with an electron-donating monomer in the presence of acatalyst in an organic solvent system under an inert gas atmosphere, and finally carrying out column chromatography purification to prepare a target product. The benzothiadiazole group used in the invention has a certain rigid planar structure and good carrier transport properties, and can form an acceptor-donor-acceptor (A-D-A) conjugated structure with an electron donating group to achieve a lower bandgap, and broaden and enhance spectral absorption of a material, and the A-D-A type benzothiadiazole small molecule is used to construct highly efficient organic solar cell materials. The conjugated small molecule] has good absorption and suitable energy level in a visible light range, and is applied to donor materials in an organic solar cell, and good device efficiency is obtained. The organic solar cell has a simple preparation process, large-area manufacturing is easy to realize, and the cost is low.

Description

technical field [0001] The invention belongs to the technical field of heterocyclic compounds, and in particular relates to an A-D-A type benzothiadiazole small molecule and a preparation method and application thereof. Background technique [0002] At present, the closest existing technology: energy has always been an indispensable driving force in human development and progress, and the development and utilization of energy is also a long-term topic. With the increasing global demand for energy, coal, oil, natural gas As traditional energy sources are about to run out, solar energy, as a clean energy source, is favored by people because of its inexhaustible and inexhaustible advantages. Solar cells are devices that convert solar energy into electrical energy and are considered to be the most efficient and direct form of solar energy utilization. [0003] At present, polycrystalline silicon thin-film solar cells as a representative of inorganic solar cells have been commer...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04H01L51/46
CPCY02E10/549Y02P70/50
Inventor 秦元成何安旺杜婉君周丹
Owner NANCHANG HANGKONG UNIVERSITY
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