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Organic small-molecule donor photovoltaic material containing fluorinated benzotriazole as well as preparation method and application of organic small-molecule donor photovoltaic material

An organic and photoelectric technology, applied in photovoltaic power generation, organic chemistry, silicon organic compounds, etc., can solve the problem of low photoelectric conversion efficiency, and achieve the effect of superior photovoltaic performance, easy purification, and structure determination.

Inactive Publication Date: 2017-11-21
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Small organic molecules have the potential advantages of definite molecular structure, no batch difference, simple synthesis and purification, and low cost. However, the photoelectric conversion efficiency of non-fullerene solar cells based on organic small molecule donor materials is lower than that of polymer solar cells. Therefore, the development of a class of high-efficiency organic small molecule donor materials that match non-fullerene acceptors has become a research hotspot.

Method used

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  • Organic small-molecule donor photovoltaic material containing fluorinated benzotriazole as well as preparation method and application of organic small-molecule donor photovoltaic material
  • Organic small-molecule donor photovoltaic material containing fluorinated benzotriazole as well as preparation method and application of organic small-molecule donor photovoltaic material
  • Organic small-molecule donor photovoltaic material containing fluorinated benzotriazole as well as preparation method and application of organic small-molecule donor photovoltaic material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] The organic photoelectric compound of this embodiment is composed of a large organic conjugated unit system and an alkane or alkane-like structure, and is a black solid powder with metallic luster. The general chemical structure of the compound is shown in Formula II:

[0064]

[0065] where: R 6 is 2-ethylhexyl, R 7 It is 2-hexyloctyl, that is, the chemical structural formula of the compound is as shown in formula II-1:

[0066]

[0067] The preparation method of the organic photoelectric compound used in solar cells is prepared by carrying out Knoevenagel condensation reaction of a dialdehyde terminal compound and a terminal precursor compound, comprising the following steps:

[0068] 1) Under argon protection, 5-(7-(5-bromothiophen-2-yl)-5,6-difluoro-2-(2-hexyldecyl)-2H-benzo[d][1 ,2,3] Triazol-4-yl)thiophene-2-carbaldehyde 3.25g (5.0mmol) and 2-ethylhexylthienyl substituted benzodithiophene bistin monomer 2.26g (2.5mmol), 30mL Dried toluene and triphenylpho...

Embodiment 2

[0076] The organic photoelectric compound of this embodiment is composed of a large organic conjugated unit system and an alkane or alkane-like structure, and is a black solid powder with a metallic luster. The general chemical structure of the compound is shown in Formula V below:

[0077]

[0078] Among them, R 7 is 2-hexyloctyl, R 8 Be 2-ethylhexyl, that is, the chemical structural formula of the compound is formula V-1:

[0079]

[0080] The preparation method of the organic photoelectric compound for solar cells is basically the same as that of Example 1, except that the benzodithiophene ditin monomer replaced by thiophene ditin monomer is replaced by 2-ethylhexylthiophene ditin monomer, and also Using chloroform as a solvent and piperidine as a catalyst, an organic photoelectric compound is prepared with a yield of 85%.

[0081] 1 H NMR (400MHz, CDCl3): δ (ppm) 8.21-8.20 (m, 4H), 8.18 (s, 2H), 7.77-7.76 (d, 2H), 7.11-7.10 (m, 4H), 4.75-4.74 ( d,4H),4.17-4.09(m,...

Embodiment 3

[0085] Example 3. Film-forming and solubility tests of small molecules of the present invention.

[0086] Place the compounds shown in formula II-1 and formula V-1 prepared in Example 1 and Example 2 in several common organic solvents, such as chlorobenzene, dichlorobenzene, chloroform, toluene, trichlorobenzene, methanol Wait. The compound was found to have good solubility in chlorinated solvents, but was insoluble in methanol. High-quality films can be prepared by spin-coating the trichloride solution of the compound on a glass slide.

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Abstract

The invention discloses an organic small-molecule donor photovoltaic material containing fluorinated benzotriazole as well as a preparation method and application of the organic small-molecule donor photovoltaic material. The organic small-molecule donor photovoltaic material has a structural formula as shown in formula I, wherein X is H or F; Z is O, S or Se; R1, R2 and R3 are independently selected from H, C1-C30 alkyl groups, C3-C30 naphthenic bases, C1-C30 alkoxy groups, C1-C30 alkyl sulphanyls, halogeneated C1-C30 alkyl groups, halogeneated C3-C30 naphthenic bases and halogeneated C1-C30 alkoxy groups; each of A1 and A2 is an organic conjugated unit; and n is a natural number from 1 to 10. The application of an organic photoelectric compound to the following functional energy devices including a solar battery, a field effect transistor, an organic light emitting diode and a photovoltaic device also belongs to the protection scope of the invention. The organic photoelectric compound provided by the invention is simple in synthesis step, easy to purify and determined in structure; and the organic photovoltaic device prepared from the organic photoelectric material provided by the invention has excellent photovoltaic property, and the photoelectric conversion efficiency can reach 9.5%.

Description

technical field [0001] The invention relates to an organic small molecule donor photovoltaic material containing fluorine-banded benzotriazole, a preparation method and application thereof. Background technique [0002] With the increasing depletion of fossil energy, energy shortage has become an urgent problem in the world; solar energy has the advantages of cleanness, greenness, pollution-free, wide distribution, and renewable, and has the most development prospects. The development and utilization of solar energy will be an effective way to deal with the energy crisis. Solution. Due to the advantages of low cost, light weight, bendability, solution processability and large area preparation, organic solar cells have received extensive attention in academia. So far, through the optimization of molecular structure, device structure and processing technology, the photoelectric conversion efficiency of solar cells based on the blending of polymer donors or small molecule dono...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04C07D409/14C07F7/08C07F7/10H01L51/46
CPCC07D409/14C07D495/04C07F7/0814C07F7/083H10K85/626H10K85/655H10K85/6572H10K85/6576H10K85/40Y02E10/549
Inventor 张志国宾海军李永舫
Owner INST OF CHEM CHINESE ACAD OF SCI
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