ADA’DA type fully fused ring small molecules and their preparation methods and applications

A technology of small molecules and fused rings, which is applied in semiconductor/solid-state device manufacturing, organic chemistry, electric solid-state devices, etc., can solve the problems of poor stability of photovoltaic small-molecule acceptor materials, and achieve favorable charge transport properties and easy photoelectric properties. , is conducive to the effect of solid accumulation

CN113583019BActive Publication Date: 2022-07-19CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Publication Date
2022-07-19

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Abstract

The invention relates to an ADA'DA type fully fused ring organic small molecule and its preparation method and application, and belongs to the technical fields of organic functional materials and photovoltaic cells. The technical problem of poor stability of photovoltaic small molecule receptor materials in the existing technology is solved. The organic small molecule provided by the invention adopts a completely condensed ADA'DA configuration molecular skeleton, in which A' is the central core, A is the terminal group, A' and A are electron-pulling units, and D is the connecting unit. Electronic unit. Experimental results show that this ADA'DA type fully fused ring organic small molecule has high chemical stability and photostability, good skeleton planarity, and excellent charge transport properties. By regulating the central core, connecting units and end groups, respectively The ability to push and pull electrons can achieve precise control of HOMO / LUMO energy levels, thereby achieving control of the absorption spectrum. It can be used as an electron acceptor in organic solar cells to achieve excellent device performance.
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Description

Technical field

[0001] The invention belongs to the technical field of organic functional materials and photovoltaic cells, and specifically relates to an ADA'DA type fully fused ring organic small molecule and its preparation method and application. Background technique

[0002] Organic solar cells are flexible, lightweight, translucent, and can be processed by low-cost solutions, and are expected to be used in portable, wearable energy and building-integrated photovoltaic technologies. The core of organic solar cell research is an active layer composed of a blend of electron donors and electron acceptors, and both polymers and small molecules can serve as electron donors or electron acceptors. Compared with polymers, small organic molecules have a definite structure and do not have batch repeatability problems, which have advantages in practical application development. In recent years, the rapid development of non-fullerene small molecule electron acceptor materials has ...

Examples

Embodiment 1

[0084] ADA'DA type fully fused ring small molecule 1, the structural formula is as follows:

[0085]

[0086] The preparation method of above-mentioned ADA 'DA type fully fused ring small molecule:

[0087] Step 1. Take a 500mL double-neck flask, bake the flask, add compound 1-1 (6.1g, 22.90mmol), add ethylene glycol (30mL), p-toluenesulfonic acid (394.0mg, 2.29mmol), add benzene (300mL) , pumped and ventilated three times, and heated and refluxed for 36h at 115°C under the protection of argon atmosphere. Naturally returned to room temperature, water was added to quench the reaction system, the reaction solution was extracted with ether three times, the organic phase was washed with distilled water and saturated brine successively, dried over anhydrous sodium sulfate, and concentrated. The crude product was purified by column chromatography to obtain compound 1-2 (3.3 g, yield 47.0%). NMR analysis: 1 H NMR (500MHz, CDCl 3 )δ7.37(d,J=7.4Hz,1H),7.29(t,J=7.5Hz,1H),7.22(d,J...

Embodiment 2

[0110] ADA'DA type fully fused ring small molecule 2, the structural formula is as follows:

[0111]

[0112] The preparation method of above-mentioned ADA 'DA type fully fused ring small molecule, the steps are as follows:

[0113] Step 1. Take a 250mL single-neck round-bottomed flask, add compound 2-1 (3.0g, 7.58mmol), and draw and ventilate it for three times. Trifluoromethanesulfonic acid (10.9g, 75.80mmol) is added dropwise at 0°C, and the reaction is stirred at room temperature for 3h. , fuming nitric acid (9.5 g, 151.60 mmol) was added dropwise, and the mixture was heated and stirred at 50°C overnight under the protection of argon atmosphere. The reaction solution was poured into ice water to quench the reaction, the reaction solution was extracted with DCM three times, the organic phase was washed with distilled water and saturated brine in sequence, dried over anhydrous sodium sulfate, and concentrated. After purification by column chromatography, compound 2-2 (2.2 ...

Embodiment 3

[0129] ADA'DA type fully fused ring small molecule 3, the structural formula is as follows:

[0130]

[0131] The preparation method of the above-mentioned ADA'DA type fully fused ring small molecule 3 is the same as the preparation method of the ADA'DA type fully fused ring small molecule 2 in Example 2, the difference is that the 2-tributylstannylthiophene in the raw material is replaced. It is 2-tributylstannyl selenol.

[0132] Elemental analysis structure of ADA'DA type fully fused ring small molecule 3 (C 58 H 59 N 9 Se 2 ): Theoretical: C, 66.98; H, 5.72; N, 12.12. Tested: C, 66.91; H, 5.75; N, 12.30.

[0133] MALDI-TOF analysis, theoretical value: 1041.3; experimental value: 1041.3.