A-pi-D-pi-A type small molecule solar cell receptor material based on thiophene indenone and fluorene and preparation method of A-pi-D-pi-A type small molecule solar cell receptor material

A solar cell and thienindanone technology, which is applied in the fields of electrical solid-state devices, semiconductor/solid-state device manufacturing, circuits, etc., can solve the problems of insufficient molecular design, synthesis route optimization, low photovoltaic efficiency, single structure, etc., and achieve stable photochemistry properties, high molar extinction coefficient, strong UV absorption effect

Inactive Publication Date: 2020-02-14
DONGGUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, so far, there are not many reports on the application of organic small molecule solar cells with thienindanone as the capping group, lack of sufficient design of molecules and necessary optimization of synthetic routes, and the existence of single structure and low photovoltaic efficiency. advanced questions

Method used

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  • A-pi-D-pi-A type small molecule solar cell receptor material based on thiophene indenone and fluorene and preparation method of A-pi-D-pi-A type small molecule solar cell receptor material
  • A-pi-D-pi-A type small molecule solar cell receptor material based on thiophene indenone and fluorene and preparation method of A-pi-D-pi-A type small molecule solar cell receptor material
  • A-pi-D-pi-A type small molecule solar cell receptor material based on thiophene indenone and fluorene and preparation method of A-pi-D-pi-A type small molecule solar cell receptor material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Synthesis of target molecule FTC1

[0063] Add intermediate 2 (152mg, 0.25mmol), thienindanone (200mg, 1mmol), chloroform (20mL) and magnetons into a dry and clean 50mL three-necked flask, stir and dissolve the reactants, and evacuate the system into a vacuum state. And replace with argon, add pyridine (1mL) under argon atmosphere, react at room temperature for 12h, point the plate to monitor until the reaction is complete, add 10mL of water to quench the reaction, let the system cool to room temperature, and extract with an appropriate amount of dichloromethane for 3 -5 times, then washed with an appropriate amount of saturated NaCl solution for 3-5 times, kept the organic phase and added an appropriate amount of anhydrous MgSO 4 The powder was dried, excess solvent was removed, separation and purification by silica gel column chromatography (petroleum ether:dichloromethane:ethyl acetate=12:2:1) gave dark blue solid powder target molecule FTC1 (146mg, 60%). 1 HNMR (40...

Embodiment 2

[0065] Synthesis of target molecule FTC2

[0066] The synthesis method of the target molecule FTC2 is similar to that of the target molecule FTC1. Intermediate 3 (145 mg, 0.25 mmol) and thienindanone (200 mg, 1 mmol) were used as reactants to separate and purify the target molecule FTC2 (148 mg, 63 %). 1 H NMR (400MHz, CDCl 3 )δ: 8.81(d, J=3.9Hz, 1H), 8.49(s, 1H), 8.33(d, J=2.2Hz, 1H), 7.88(d, J=2.2Hz, 1H), 7.84(d, J=8.8Hz,1H),7.76(s,1H),7.74(s,1H),7.12(d,J=4.0Hz,1H),2.08–2.02(m,2H),1.03(dd,J=32.5 ,5.7Hz,10H),0.69(t,J=7.0Hz,3H),0.52(dd,J=13.1,6.6Hz,2H). 13 C NMR (101MHz, CDCl 3 )δ:162.88,156.63,152.58,150.87,143.58–142.08,131.92,130.16,129.16,127.93,127.67,125.48,121.18,119.88,115.12,114.15,112.51,107.98,77.21,76.86,76.73,70.02–68.05,67.87 , 55.86, 40.21, 32.89–32.10, 31.76, 29.51, 23.84, 22.58, 14.07. MALDI-TOF-MS, m / z: calcd for C 59 h 50 N 4 o 4 S 2 [M] + :942.327; found 943.525.

Embodiment 3

[0068] Synthesis of target molecule FTC3

[0069] The synthesis method of the target molecule FTC3 is similar to that of the target molecule FTC1, with intermediate 4 (149 mg, 0.25 mmol) and thienindanone (200 mg, 1 mmol) as reactants, separated and purified to obtain a deep red solid powder target molecule FTC3 (120 mg, 50 %). 1 H NMR (400MHz, CDCl 3 )δ:8.84(s,1H),8.42(s,1H),7.99(s,1H),7.88(d,J=4.0Hz,1H),7.87(dd,J=13.8,6.0Hz,2H), 7.84–7.77(m, 2H), 7.77(s, 1H), 7.62(d, J=4.1Hz, 1H), 2.10(d, J=7.8Hz, 2H), 1.11(d, J=29.8Hz, 11H ),0.77(t,J=6.7Hz,4H),0.65(s,2H). 13 CNMR (101MHz, CDCl 3)δ:181.51,173.41,161.40,156.23,152.61,146.46,142.73–142.11,139.29,136.40,132.66,128.67,127.94,126.24,125.73,125.16,121.10,120.88,114.91,114.03,77.36,77.04,76.73,68.33 ,55.89,51.63,40.27,33.06,31.75,29.89,29.21,23.85,22.59,20.11,14.06.MALDI-TOF-MS,m / z: calcd for C 63 h 54 N 4 o 2 S 2 [M] + :962.369; found 963.428.

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Abstract

The invention discloses an A-pi-D-pi-A type small molecule solar cell receptor material based on thiophene indenone and fluorene and a preparation method of the A-pi-D-pi-A type small molecule solar cell receptor material. According to the receptor material, fluorine is adopted as a central core structure, groups such as thiophene, furan and benzene are adopted as pi bridges, and aldehyde groups at both ends are subjected to a condensation reaction with active sites of an electrondrawing group thiophene indanone to obtain symmetric target molecules at normal temperature and normal pressure. The A-pi-D-pi-A type small molecule solar cell receptor material based on thiophene indenone and fluorine is simple in synthesis method, easy in reaction condition control, high in yield, good in universal applicability and possible in efficient synthesis, can be widely applied to fields such as energy, life, analysis, material science, and the like, and is particularly suitable for being used as organic small molecule solar cell receptor materials, and the like.

Description

Technical field: [0001] The invention relates to a solar cell acceptor material, in particular to an A-π-D-π-A type small molecule solar cell acceptor material based on thienindanone and fluorene and a preparation method thereof. Background technique: [0002] Thiphenindanone is a new type of electron-withdrawing group that has only been developed in recent years and has received widespread attention and attention. Thiphenindanone derivatives are a class of good photosensitive materials with good stability, high molar Extinction coefficient and narrow energy gap, and when it is used as the capping group of symmetrical small molecule acceptor material, it shows good photophysical and chemical properties, stable performance and high energy conversion efficiency. Therefore, acceptor materials for small-molecule solar cells with thienindanes as capping groups have good application prospects in the field of organic small-molecule solar cells. [0003] However, so far, there are ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/78C07D409/14H01L51/42H01L51/46
CPCC07D333/78C07D409/14H10K85/615H10K85/653H10K85/655H10K85/6576H10K30/00Y02E10/549
Inventor 赵鸿斌廖俊旭沈松平徐键郑培锦徐耿标孔浩君余贺宇
Owner DONGGUAN UNIV OF TECH
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