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A kind of organic small molecule semiconductor material containing rhodanine fused isatin and its preparation method and application

A rhodanine and small molecule technology, which is applied in the field of organic small molecule semiconductor materials containing rhodanine fused isatin and its preparation, can solve the problems of poor stability, achieve enhanced stability, novel molecular structure, good The effect of response

Active Publication Date: 2021-08-10
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved by the present invention is to provide a small organic molecule semiconductor material containing rhodanine fused isatin and its preparation method and application, which overcomes the problems of poor stability of existing materials

Method used

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  • A kind of organic small molecule semiconductor material containing rhodanine fused isatin and its preparation method and application
  • A kind of organic small molecule semiconductor material containing rhodanine fused isatin and its preparation method and application
  • A kind of organic small molecule semiconductor material containing rhodanine fused isatin and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Add isatin (1equiv) and potassium carbonate (2.5equiv) to the reaction flask, add anhydrous DMF and tetrahydrofuran after ventilation, slowly add alkyl bromide to the flask, and react at 50°C after dripping overnight. After extraction with dichloromethane and water, the organic phases were combined and dried over anhydrous magnesium sulfate. After spin-drying dichloromethane, the product was separated and purified by column chromatography to obtain a yellow solid product. The H NMR and C NMR spectra of 6-bromoisatin are consistent with the literature (Li, J.-L.; Chai, Y.-F.; Wang, W.V.; Shi, Z.-F.; Xu, Z.-G .; Zhang, H.-L., Chem. Commun. 2017, 53, 5882. Luo, X.; Tran, D.T.; Kadlubowski, N.M.; ., Macromolecules, 2018, 51, 8486.)

[0046]The preparation of 6-bromo-1-methylindoline-2,3-dione, the reaction formula is as follows:

[0047]

[0048] The preparation of 6-bromo-1-butylindoline-2,3-dione, the reaction formula is as follows:

[0049]

[0050] The prepar...

Embodiment 2

[0060] Add four-p-hexylbenzene-indaprodithiophene bistin (1equiv) and 6-bromoisatin (2.5equiv) in the reaction flask, add ultra-dry toluene and catalyst Pd (PPh 3 ) 4 (5% equiv), heated to 125°C to react overnight. After cooling to room temperature, it was extracted with chloroform and water. The organic phases were combined and dried with anhydrous magnesium sulfate, evaporated to dryness and purified by column chromatography to obtain a black solid product. All the obtained compounds were verified as target products by H NMR and C NMR spectra.

[0061] When isatin is 6-bromo-1 methylindoline-2,3-dione, the reaction formula is as follows:

[0062]

[0063] When isatin is 6-bromo-1-octyl indoline-2,3-dione, the reaction formula is as follows:

[0064]

[0065] When isatin is 6-bromo-5-fluoro-1-octylindoline-2,3-dione, the reaction formula is as follows:

[0066]

[0067] When isatin is 6-bromo-5-fluoro-1-octylindoline-2,3-dione, the reaction formula is as follows...

Embodiment 3

[0074] Add the three compound intermediates (1equiv) and (alkyl) rhodanine (5equiv) obtained in Example 2 in the reaction flask, add chloroform after pumping, add a few drops of triethylamine after stirring for 5 minutes, room temperature React overnight. Extract with chloroform and water, combine the organic phases, and dry the organic phases with anhydrous magnesium sulfate. After evaporating chloroform to dryness, the product was purified by column chromatography to obtain a green solid product.

[0075]

[0076] The H NMR and C NMR spectra of compound WH7 are characterized as follows:

[0077] 1 H NMR (400MHz, CDCl 3 ,298K):8.83(s,1H),7.48(d,1H),7.41(s,1H),7.35(d,1H),7.23(d,4H),7.13(d,4H),7.03(s, 1H), 4.33(q, 2H), 3.81(t, 2H), 2.58(t, 4H), 1.72(m, 2H), 1.60(t, 4H), 1.45-1.19(m, 25H), 0.84(m ,9H). 13 C NMR (100MHz, CDCl 3 ,298K):182.18,159.05,157.80,154.20,151.91,145.52,144.59,144.04,142.17,141.24,135.61,128.70,127.96,122.23,120.08,118.07,116.23,106.06,63.37,40.37...

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Abstract

The invention relates to a small organic molecule semiconductor material containing rhodanine fused (like) isatin and its preparation method and application. The general structural formula of the material is shown in Formula I. The invention has excellent solubility, is soluble in common organic solvents, and can be used for solution processing to prepare organic optoelectronic devices; it has good response to the solar spectrum and good frontier molecular orbital energy levels, and the molecules have good planarity. It has high electron mobility and can be used as a small molecule acceptor material in the active layer material of organic solar cells.

Description

technical field [0001] The invention belongs to the field of organic semiconductor materials, and in particular relates to an organic small molecule semiconductor material containing rhodanine-fused isatins, a preparation method and application thereof. Background technique [0002] A solar cell is a device that directly converts light energy into electrical energy through the photoelectric effect. Silicon solar cells that work by the photoelectric effect are the mainstream of current technology. However, the production of silicon solar cells consumes a lot of energy and causes great pollution to the environment. Organic solar cells use organic materials to form the core part, and also use the photoelectric effect to generate voltage and form current to achieve the effect of solar power generation. Organic solar cells are not only light in weight, but also can be prepared in a roll-to-roll method, which greatly reduces production costs and is expected to become a commercial...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04C07D495/22C07D517/22C07D519/00C07F7/08H01L51/30H01L51/46
CPCC07D495/04C07D495/22C07D517/22C07D519/00C07F7/0816H10K85/6576H10K85/6572H10K85/657H10K10/46H10K30/00Y02E10/549
Inventor 王明黄峻李正王锴高佳欣郭雨晴
Owner DONGHUA UNIV
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