Organic electron acceptor material and preparation method and application thereof

A technology for acceptor materials and organic electronics, which is applied in the field of organic electron acceptor materials and their preparation, and can solve the problems that star-shaped non-fullerene electron acceptor materials have not been optimized.

Pending Publication Date: 2021-09-14
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, compared with the extensive research on linear non-fullerene electron acceptor materials, star-shaped non-fullerene electron acceptor materials have not been optimized.

Method used

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  • Organic electron acceptor material and preparation method and application thereof
  • Organic electron acceptor material and preparation method and application thereof
  • Organic electron acceptor material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] The preparation process of S-3 compound is shown in Figure 5 .

[0038] Specific steps are as follows:

[0039] The first step: take 4,4,9,9-tetraoctyl-4,9-dihydro-s-indan[1,2-b:5,6-b']dithiophene (C-3)( 996.0mg, 1.394mmol), N-N dimethylformamide (a) (157.9mg, 1.812mmol) and phosphorus oxychloride (b) (256.5mg, 1.673mmol) in the reaction flask, then add 20mL 1,2- Dichloroethane was reacted 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 distillation under reduced pressure, purified by silica gel column chromatography, and finally spin-dried to obtain c (403.5 mg, 40.0%).

[0040] Step II: Dissolve compound c (389.4mg, 0.524mmol) in 10mL of dichloromethane in a reaction flask, and put it in an ice-water bath to stir in the dark. Take N-bromosuccinimide (d) (121.2mg, 0.681mmol) and dissolve it in 10mLDMF, and drop it into two-necked reaction ...

Embodiment 2

[0045] For the preparation process of S-10 compound see Image 6 .

[0046] Formula S-10 was prepared in a similar manner to compound S-3, except that C-10 was used to replace 4,4,9,9-tetraoctyl-4,9-dihydro-s-indan[1,2 -b:5,6-b']dithiophene (C-3). The yield of the first step is 41.1%, the yield of the second step is 89.8%, the yield of the third step is 39.5%, and the yield of the fourth step is 85.3%.

[0047] Compound S-10 product MS (m / z): 2960.09; Elemental analysis (C 171 h 180 f 6 N 6 o 15 S 9 ): C, 69.34; H, 6.13; F, 3.85; N, 2.84; O, 8.10; S, 9.74.

Embodiment 3

[0049] The preparation process of S-18 compound is shown in Figure 7 .

[0050] Formula S-18 was prepared in a similar manner to compound S-3, except that C-18 was used to replace 4,4,9,9-tetraoctyl-4,9-dihydro-s-indan[1,2 -b:5,6-b']dithiophene (C-3). The yield of the first step is 41.7%, the yield of the second step is 88.9%, the yield of the third step is 39.7%, and the yield of the fourth step is 86.2%.

[0051] Compound S-18 product MS (m / z): 3801.60; Elemental analysis (C 219 h 252 f 6 N 6 o 27 S 9 ): C, 69.17; H, 6.68; F, 3.00; N, 2.21; O, 11.36; S, 7.59.

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Abstract

The invention discloses an organic electron acceptor material and a preparation method and application thereof. The organic electron acceptor material is characterized in that a benzotrithiophene electron-donating group serves as a central core unit, an indacenodithiophene fused ring structure serves as an arm unit, the fused ring structure is modified through a side chain structure, and a 3-(dicyanomethylene)indanone group and a derivative thereof are used for end capping at a terminal group. Thus, the organic electron acceptor material is obtained. The material has general advantages of linear non-fullerene, such as strong light absorption, adjustable energy level, good solubility, high morphological stability and the like, and also has high electron mobility and isotropic charge transfer characteristics of a fullerene material. Besides, the three-dimensional geometric structure is beneficial to intramolecular charge transfer, so that the energy gap is reduced, the absorption range is expanded, the performance of the device is improved, the device shows extremely high short-circuit current and fill factor, and the power conversion efficiency of the solar cell is also greatly improved.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials and applications, and in particular relates to an organic electron acceptor material and its preparation method and application. Background technique [0002] Nonfullerene acceptors have achieved great success due to their tunable absorption spectra and energy levels, good chemical and photostability, and good compatibility with donors to form suitable morphologies. Most high-performance small-molecule non-fullerene electron acceptors have a linear structure consisting of an electron-donating core unit and two electron-deficient capping groups (type A-D-A), such as ITIC, IDTBR, and Y6. However, controlling the direction of molecular packing is a limitation of small-molecule nonfullerene electron acceptors, as they tend to assume a frontal or sideways orientation depending on chemical structure and processing conditions. [0003] With the emergence of the A-D-A type small molecule ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00H01L51/42H01L51/46
CPCC07D519/00H10K85/615H10K85/6576H10K30/00Y02E10/549Y02P70/50
Inventor 赖文勇张超汪洋李祥春王倩陈劲
Owner NANJING UNIV OF POSTS & TELECOMM
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