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Non-fullerene electron acceptor material and preparation method and application thereof

An electron acceptor material, non-fullerene technology, applied in electric solid state devices, chemical instruments and methods, semiconductor/solid state device manufacturing, etc., can solve the problems of poor material film stability and limited isotropic charge transport, etc. Achieve the effect of mature synthesis process, excellent solubility and film formation, and excellent molar absorption coefficient

Active Publication Date: 2021-09-03
NANJING UNIV OF POSTS & TELECOMM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Excellent optoelectronic properties can be achieved by optimizing the device structure and implementation conditions, which can overcome the prohibition of optical transitions caused by the highly symmetric wave function of the fullerene electron acceptor, the poor stability of the material film, and the isotropic charge transport in the three-dimensional direction of the linear electron acceptor. limited technical issues

Method used

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  • Non-fullerene electron acceptor material and preparation method and application thereof
  • Non-fullerene electron acceptor material and preparation method and application thereof
  • Non-fullerene electron acceptor material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] For the preparation of compound S-1, see Figure 5 ;

[0038] Specific steps are as follows:

[0039] Step Ⅰ: Take 4,4,9,9-tetraoctyl-4,9-dihydro-s-indan[1,2-b:5,6-b']dithiophene (a) (996.0mg , 1.394mmol), N-N dimethylformamide (b) (157.9mg, 1.812mmol) and phosphorus oxychloride (256.5mg, 1.673mmol) in the reaction flask, then add 20mL 1,2-dichloroethane, React at 100°C for 24h. The obtained mother liquor was washed with water, extracted with dichloromethane, dried with anhydrous sodium sulfate, then evaporated the excess solvent by vacuum distillation, purified by silica gel column chromatography, and finally obtained solid c (403.5 mg, 40.0%) after spin-drying.

[0040] Step II: Compound c (389.4mg, 0.524mmol) was dissolved in 10mL of dichloromethane in a reaction flask, protected from light, and stirred in an ice-water bath. Take N-bromosuccinimide (d) (121.2mg, 0.681mmol) and dissolve it in 10mLDMF, and drop it into two-necked reaction flasks drop by drop, react...

Embodiment 2

[0045] The preparation step of S-2 compound sees Figure 6 .

[0046] Formula S-2 was prepared in a similar manner to compound S-1, except that 1,3,5-benzenetriboronic acid tripinacol ester (H-1) was replaced by H-2. The yield of the first step is 41.8%, the yield of the second step is 91.7%, the yield of the third step is 38.6%, and the yield of the fourth step is 90.4%.

[0047] Compound S-2 product MS (m / z): 3113.68; Elemental analysis (C 203 h 236 f 6 N 6 o 3 S 6 ): C, 78.29; H, 7.64; F, 3.66; N, 2.70; O, 1.54; S, 6.18.

Embodiment 3

[0049] The preparation process of S-7 compound is shown in Figure 7 :

[0050] Formula S-7 was prepared in a similar manner to compound S-1, except that H-7 was used in place of 1,3,5-benzenetriboronic acid tripinacol ester (H-1). The yield of the first step is 40.6%, the yield of the second step is 90.3%, the yield of the third step is 37.5%, and the yield of the fourth step is 91.4%.

[0051] Compound S-7 product MS (m / z): 3243.68; Elemental analysis (C 207 h 234 f 6 N 12 o 3 S 6 ): C, 76.63; H, 7.27; F, 3.51; N, 5.18; O, 1.48; S, 5.93.

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Abstract

The invention discloses a non-fullerene electron acceptor material and a preparation method and application thereof. The star-shaped non-fullerene electron acceptor material is obtained by taking an electron donating structure as a central core unit and a five-membered fused ring as an arm unit, and blocking a terminal group by using electron withdrawing groups such as 3-(dicyanomethylene) indanone and derivatives thereof. The material not only maintains the advantages of a linear non-fullerene electron acceptor material, but also has high electron mobility and isotropic charge transfer characteristics of a fullerene electron acceptor material, and the multidimensional geometric structure of the material is beneficial to intramolecular charge transfer, so that the energy gap is reduced and the absorption range is expanded, and the star-shaped multi-dimensional structure can effectively inhibit excessive aggregation and is beneficial to exciton dissociation. The material can be used as an electron acceptor material of an active layer to be widely applied to preparation of organic solar cells, and excellent material film stability and excellent photoelectric conversion characteristics can be obtained.

Description

technical field [0001] The invention belongs to the field of photoelectric materials and applications, and in particular relates to a non-fullerene electron acceptor material and its preparation method and application. Background technique [0002] Organic solar cells are considered to be one of the most promising photovoltaic technologies due to their ease of fabrication, light weight, flexibility, low toxicity, and abundant raw materials. The energy conversion efficiency of bulk heterojunction solar cells with bicontinuous interpenetrating network structure has been continuously improved and has recently increased to more than 18%. Among them, the active layer combining the electron donor (D) material and the electron acceptor (A) material plays a decisive role in the power conversion efficiency. Therefore, how to design efficient organic semiconductor materials becomes the key to improving device performance. Among the many small molecule non-fullerene electron acceptor...

Claims

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Application Information

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IPC IPC(8): C07D519/00C07F7/08C07F7/30H01L51/46
CPCC07D519/00C07F7/0812C07F7/30H10K85/624H10K85/655H10K85/626H10K85/615H10K85/631H10K85/30H10K85/6576H10K85/657H10K85/40H10K85/6572Y02E10/549Y02P70/50
Inventor 赖文勇张超汪洋李祥春耿海港闵洁
Owner NANJING UNIV OF POSTS & TELECOMM
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