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Organic solar cell acceptor material using diindeno bithiophene as core, preparation method and applications thereof

A technology for solar cells and acceptor materials, applied in the field of organic solar cell acceptor materials and their preparation, can solve the problems of single chemical structure, unfavorable acceptor stacking arrangement, limited regulation of material band gap and spectral absorption, etc. Simple preparation process

Inactive Publication Date: 2020-02-04
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The structure of the fused-ring small molecule receptors reported so far is relatively complex, the synthetic raw materials are expensive and the preparation process is difficult, the chemical structure is relatively simple, and the adjustment of the band gap and spectral absorption of the material is relatively limited.
At the same time, the structure of the existing small molecule acceptor material is relatively rigid, and most of the electron-donating nuclei in the middle of the condensed ring form sp 2 Hybrid orbitals are not conducive to the stacking arrangement of the donor acceptor and affect the phase separation of the active layer

Method used

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  • Organic solar cell acceptor material using diindeno bithiophene as core, preparation method and applications thereof
  • Organic solar cell acceptor material using diindeno bithiophene as core, preparation method and applications thereof
  • Organic solar cell acceptor material using diindeno bithiophene as core, preparation method and applications thereof

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Experimental program
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Effect test

Embodiment 1

[0057] The structural formula of the organic solar cell acceptor material (SMOPV-1) in which the conjugated fused ring small molecule is the nucleus of this embodiment is:

[0058]

[0059] The preparation method of SMOPV-1 comprises the following steps (1)~(8):

[0060] (1) Synthesis of compound 1:

[0061]

[0062] Take a single-necked round-bottom flask, add N-chlorosuccinimide to the N,N-dimethylformamide solution of thiophene and stir at room temperature for several hours, monitor by TLC, add water to quench the reaction, and The liquid was transferred to a separatory funnel and extracted with ether, the organic phase was dried with anhydrous sodium sulfate, spin-dried and passed through the column with petroleum ether eluent to obtain a white solid, namely the double-sided chlorinated thiophene product 1; wherein, N-chloro The ratio of succinimide, thiophene and N,N-dimethylformamide is 10-20mmol:20-50mmol:40-100mL; the yield is 90.4%; the structural characterizat...

Embodiment 2

[0086] The structural formula of the organic solar cell acceptor material (SMOPV-2) in which the conjugated fused ring small molecule is the nucleus of this embodiment is:

[0087]

[0088] The preparation method of SMOPV-2 comprises following steps (1)~(8):

[0089] Wherein, steps (1) to (7) in the preparation method of SMOPV-2 are the same as the preparation steps (1) to (7) in Example 1;

[0090] (8) Synthesis of compound 9-2:

[0091]

[0092] Take a double-necked round-bottom flask, dissolve compound 8-1 in chloroform, and carry out Knoevenagel condensation reaction with difluoromalononitrile indanone pulling electron unit under weakly alkaline conditions. After the reaction is monitored by TLC, the reaction solution is directly Pass through the column with petroleum ether / dichloromethane eluent to obtain the finally described organic solar cell with bisindenobithiophene as the core; wherein, the proportion of compound 8-1, electron-drawing unit, pyridine, and chloro...

Embodiment 3

[0094] The structural formula of the organic solar cell acceptor material (SMOPV-3) in which the conjugated fused ring small molecule is the nucleus of this embodiment is:

[0095]

[0096] The preparation method of SMOPV-3 comprises the following steps (1)~(8):

[0097] Wherein, steps (1) to (6) in the preparation method of SMOPV-3 are the same as the preparation steps (1) to (6) in Example 1;

[0098] (7) Synthesis of compound 8-2:

[0099]

[0100] Take a double-necked round-bottom flask, anhydrous and anaerobic treatment, add the product 7, the π electron linking unit is 5-bromo-4-((2-ethylhexyl)oxy)thiophene-2-carbaldehyde, tetratriphenyl Phosphine palladium catalyst, cesium carbonate, replace the gas 3 times, add toluene under the protection of nitrogen to carry out Suzuki coupling reaction, heat the reaction solution to reflux reaction overnight, TLC monitoring after the reaction is completed, cool to room temperature, add water to quench, and transfer the reacti...

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Abstract

The invention discloses an organic solar cell acceptor material using diindeno bithiophene as a core, wherein diindenothieno[2,3-b]thiophene hexacycle is used as a central electron donating unit, anda pi electron connecting unit and a terminal electron drawing unit are introduced to form an organic acceptor material with an A-Q-D-Q-A type structure, and the structural drawing is defined in the specification. The preparation method comprises: using a strong electron donating group dithiophene as a core, introducing a benzene ring and an aromatic hydrocarbon side chain through a coupling reaction, closing the ring in an acidic environment, introducing a bridge unit with an aromatic structure, and finally adding a terminal group electron withdrawing group. According to the invention, the molecule can be used as an organic solar cell active layer acceptor material, is matched with a polymer donor energy band gap, has strong light absorption in a visible-near infrared region, is complementary with light absorption of a donor material, meets the requirement of improvement of the efficiency of organic solar cell devices, and can be used for constructing ternary organic solar cells.

Description

technical field [0001] The invention relates to the technical field of solar cell materials, in particular to a class of organic solar cell acceptor materials with bisindenobithiophene as the core, a preparation method and application thereof. Background technique [0002] With the continuous consumption of fossil energy, human beings are facing increasingly serious energy crisis and environmental problems. Solar energy is a green renewable energy source, and solar cells that convert solar energy into electrical energy have become a global research hotspot. The traditional silicon-based battery production process is complex and the inorganic materials are difficult to degrade, which is not environmentally friendly. The structure of organic solar cell materials is diverse and controllable, and the preparation is simple. It is light, flexible and can be prepared in a large area at low cost. It can be applied to portable wearable electronic devices, architectural glass and aut...

Claims

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Application Information

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IPC IPC(8): C07D495/04C07D519/00H01L51/42H01L51/46
CPCC07D495/04C07D519/00H10K85/626H10K85/656H10K85/655H10K85/6576Y02E10/549
Inventor 谢素原郑珊瑜安明伟裴亚茜邓林龙
Owner XIAMEN UNIV
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