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Merocyanine dye taking triphenylamine as donor as well as preparation method and application of merocyanine dye

A cyanine dye, triphenylamine technology, applied in the preparation of styryl dyes, organic compounds, materials of organic semiconductor devices, etc., can solve the problems of low efficiency and poor stability of perovskite solar cells, and achieve high energy conversion. Effectiveness and stability, ease of purification, high initial efficiency

Active Publication Date: 2021-06-01
HUAZHONG UNIV OF SCI & TECH +1
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  • Summary
  • 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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  • Merocyanine dye taking triphenylamine as donor as well as preparation method and application of merocyanine dye
  • Merocyanine dye taking triphenylamine as donor as well as preparation method and application of merocyanine dye
  • Merocyanine dye taking triphenylamine as donor as well as preparation method and application of merocyanine dye

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preparation example Construction

[0077] 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).

[0078]

[0079] General formula (3)

[0080] In some examples, the molar ratio of phosphorus oxychloride to N,N-dimethylformamide is 1:1-2.5. ...

Embodiment 1

[0094] Synthesis of compound MC1: the synthetic route is as figure 2 shown.

[0095] Synthesis of Unsaturated Enaldehyde BTPA-CHO

[0096] 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

[0100] Synthesis of compound MC2

[0101] 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 merocyanine dye taking triphenylamine as a donor, which is characterized in that the structure of the merocyanine dye is shown as a general formula (I) in the specification, wherein A represents an electron withdrawing group, R is independently selected from hydrogen, an unsubstituted or substituted C1-10 alkyl group, an unsubstituted or substituted C1-10 alkoxy group, and an unsubstituted or substituted aryl group, X is selected from a cyano group and an unsubstituted or substituted C1-10 alkyl ester group, and Y is oxygen, sulfur or 1, 1-dicyanomethyl. The specific chemical structure of the merocyanine dye is improved to obtain the merocyanine dye with a specific structure and triphenylamine as a donor, the merocyanine dye can be particularly applied to a perovskite solar cell as a perovskite material passivation layer, high energy conversion efficiency and stability can be obtained, and therefore, the technical problems of low efficiency, poor stability and the like of the perovskite solar cell in the prior art are solved.

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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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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