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A class of merocyanine dyes with triphenylamine as donor, its preparation method and application

A technology of cyanine dyes and triphenylamine, which is applied to the preparation of styrene-based dyes, organic compounds, materials for organic semiconductor devices, etc., can solve the problems of poor stability and insufficient efficiency of perovskite solar cells, and achieve easy purification, high High energy conversion efficiency, stability, and high yield

Active Publication Date: 2022-02-18
HUAZHONG UNIV OF SCI & TECH +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] For the above defects or improvement needs of the prior art, the object of the present invention is to provide a class of merocyanine dyes with triphenylamine as the donor, their preparation method and application, wherein by improving the specific chemical structure of the merocyanine dyes , to obtain a merocyanine dye with a specific structure using triphenylamine as a donor, especially as a perovskite material passivation layer applied to perovskite solar cells, which can obtain high energy conversion efficiency and stability, thus solving the existing Technology Perovskite solar cells have technical problems such as insufficient efficiency and poor stability

Method used

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  • A class of merocyanine dyes with triphenylamine as donor, its preparation method and application
  • A class of merocyanine dyes with triphenylamine as donor, its preparation method and application
  • A class of merocyanine dyes with triphenylamine as donor, its preparation method and application

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preparation example Construction

[0071] Regarding the preparation of unsaturated alkenal, in some embodiments, it may specifically be: adding phosphorus oxychloride dropwise to N,N-dimethylformamide in an ice-water bath under nitrogen or inert gas atmosphere. After stirring for 5-30 minutes, add 1,1-bis(4-N,N-di-p-R substituted phenylaminophenyl)ethylene in N,N-dimethylformamide solution dropwise to the above mixing in solution. After stirring for a period of time at 0-40°C (certainly also at room temperature), add an aqueous solution of sodium hydroxide to adjust the system to alkalinity, extract the reaction mixture with an organic solvent (such as dichloromethane), and dry (for example, by Add anhydrous sodium sulfate to realize), filter, and the crude product is purified by column chromatography to obtain the unsaturated alkenal shown in general formula (3).

[0072]

[0073] In some examples, the molar ratio of phosphorus oxychloride to N,N-dimethylformamide is 1:1-2.5.

[0074] In some examples, th...

Embodiment 1

[0086] Synthesis of compound MC1: the synthetic route is as figure 2 shown.

[0087] Synthesis of Unsaturated Enaldehyde BTPA-CHO

[0088] 0.14 mL of phosphorus oxychloride (1.5 mmol) was slowly added dropwise to 0.2 mL of N,N-dimethylformamide in an ice-water bath under a nitrogen atmosphere. After stirring for 15 minutes, a solution of 350 mg of 1,1-bis(4-(di-p-tolylamino)phenyl)ethylene (0.6 mmol) in 1 mL of N,N-dimethylformamide was added dropwise to the above mixed solution middle. After stirring for 5 hours at 25°C, add an aqueous solution of sodium hydroxide to adjust the system to alkalinity, extract the reaction mixture with dichloromethane, dry with anhydrous sodium sulfate, filter, and separate through a silica gel column after removing the solvent (eluent dichloromethane), the crude product was purified by column chromatography to obtain 361 mg of yellow solid BTPA-CHO with a yield of 98%. 1 H NMR (400MHz, Chloroform-d) δ9.54(d, J=8.0Hz, 1H), 7.22(d, J=8.0Hz, ...

Embodiment 2

[0092] Synthesis of compound MC2

[0093] Under nitrogen, after dissolving 180mg of unsaturated enaldehyde BTPA-CHO (0.30mmol) and 85mg of 3-ethylrhodanine (0.15mmol) in 4mL of dry tetrahydrofuran, a catalytic amount of piperin was added to the mixture Pyridine. The mixed system was heated to reflux, stirred overnight, and then separated by extraction with water and dichloromethane. The obtained organic phase is dried with anhydrous sodium sulfate, filtered, and after removing the solvent, carry out silica gel column chromatography separation (eluent is dichloromethane: sherwood oil, volume ratio is 1: 1), product ethyl acetate After recrystallization and drying, 152 mg of the red compound MC2 was obtained with a yield of 68%. 1 H NMR (600MHz, Chloroform-d) δ7.49 (d, J=12.0Hz, 1H), 7.20-7.17(m, 2H), 7.13-7.02(m, 18H), 6.99-6.96(m, 2H), 6.93-6.89(m,2H),6.43(d,J=12.0Hz,1H),4.14(q,J=7.2Hz,2H),2.33(s,6H),2.33(s,6H),1.25(t ,J=7.2Hz,3H).

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Abstract

The invention belongs to the field of organic photoelectric compounds, and discloses a class of merocyanine dyes with triphenylamine as a donor, characterized in that its structure is as shown in general formula (1); wherein, A represents an electron-withdrawing group; R is independent selected from: hydrogen, unsubstituted or substituted C 1‑10 Alkyl, unsubstituted or substituted C 1‑10 Alkoxy, unsubstituted or substituted aryl; X is selected from cyano, unsubstituted or substituted C 1‑10 Alkyl ester group; Y is oxygen, sulfur or 1,1-dicyanomethyl. The present invention improves the specific chemical structure of the merocyanine dye to obtain a specific structure of the merocyanine dye with triphenylamine as the donor, which can be used in a perovskite solar cell as a passivation layer of a perovskite material. High energy conversion efficiency and stability are obtained, thereby solving technical problems such as insufficient efficiency and poor stability of perovskite solar cells in the prior art.

Description

technical field [0001] The invention belongs to the field of organic photoelectric compounds, and more specifically relates to a class of merocyanine dyes with triphenylamine as a donor, a preparation method and application thereof. Background technique [0002] Perovskite has excellent optical absorption, tunable bandgap and long carrier lifetime, and it shines in the field of optoelectronics. After years of hard work, the photoelectric conversion efficiency of perovskite solar cells has jumped from 3.8% in 2009 to 25.5% in 2020. The perovskite layer of this type of battery device is mostly obtained through solution processing, and the coordination number of ions on the crystal surface is always lower than that in the bulk material, and the accompanying local excess of non-stoichiometric positive and negative ions leads to severe Charge recombination affects device performance. Moreover, they will cause water-oxygen degradation of the perovskite layer, which is not conduc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B23/14C07C255/42C07C253/30C07D277/36C07D277/34C07C221/00C07C223/06H01L51/42H01L51/44H01L51/46
CPCC09B23/143C09B23/145C07C255/42C07C253/30C07D277/36C07D277/34C07C221/00C07C223/06H10K30/10H10K30/88H10K2102/00Y02E10/549
Inventor 李忠安李奕彬刘宏涛
Owner HUAZHONG UNIV OF SCI & TECH
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