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Thiophene compound, preparation method and application thereof and perovskite solar battery

A technology of solar cells and compounds, applied in circuits, photovoltaic power generation, electrical components, etc., can solve the problems of low hole mobility, high price, unstable battery device performance, etc., and achieve high hole mobility and high energy conversion. The effect of efficiency

Active Publication Date: 2017-02-22
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the chemical structure of Spiro-OMeTAD is complex, the synthesis route is long, and the price is expensive. At the same time, the hole mobility of the material is low. Usually, it is necessary to use bis(trifluoromethylsulfonimide)lithium (LiTFSI), tert-butylpyridine (TBP ) and bis(trifluoromethylsulfonimide) cobalt (FK209) are p-type doped to improve hole mobility, but this type of doping will lead to unstable performance of the battery device, and the material cost is expensive

Method used

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  • Thiophene compound, preparation method and application thereof and perovskite solar battery
  • Thiophene compound, preparation method and application thereof and perovskite solar battery
  • Thiophene compound, preparation method and application thereof and perovskite solar battery

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preparation example Construction

[0048] The present invention also provides a method for preparing the above-mentioned thiophene compounds, comprising:

[0049] The compound shown in formula (II) is reacted with the compound shown in formula (III) to obtain the thiophene compound shown in formula (I);

[0050]

[0051]

[0052] Where -A- is -S-,

[0053] X is a halogen atom, preferably Cl or Br, more preferably Br;

[0054] R 1 Is H, C1~C6 hydrocarbon group or C1~C6 alkoxy group;

[0055] R 2 , R 3 with R 4Each is independently H, a C1-C6 hydrocarbon group, a C1-C6 alkoxy group or a phenyl group substituted by a C1-C6 alkoxy group.

[0056] The R 1 , R 2 , R 3 with R 4 All are the same as above, and will not be repeated here.

[0057] According to the present invention, the conditions of the reaction are Suzuki coupling reaction conditions well known to those skilled in the art, and there is no special limitation.

[0058] The organic hole transport material based on the fused ring thiop...

Embodiment 1

[0073]

[0074] In a dry Schlenk reaction flask, add 1 g of intermediate 1, 4.87 g of 4-methoxy-N-(4-methoxyphenyl)-N-(4-(4,4,5,5-tetra Methyl-1,3,2-dioxaborolan-2-yl)phenyl)amine, 3.59g sodium carbonate, then add 50mL toluene, 50mL water to dissolve, add 130mg Pd(PPh 3 ) 4 , heated to reflux, and reacted overnight under magnetic stirring.

[0075] After the reaction was detected by TLC, the reaction system was cooled to room temperature, water was added, and extracted three times with ethyl acetate, the organic phase was combined, and the organic phase was dried with anhydrous sodium sulfate, the desiccant was filtered off, spin-dried, and then washed with toluene / petroleum ether ( Volume ratio 4:1) was used as a developer for column chromatography to obtain 1.5 g of a yellow solid powder target product, ie, a thiophene compound represented by formula (I-1).

[0076] The structure of the obtained target product formula I-1 was characterized by nuclear magnetic resonance,...

Embodiment 2

[0081]

[0082] 2.1 Synthesis of the thiophene compounds shown in the target product formula (I-2)

[0083] In a dry Schlenk reaction flask, 720 mg of intermediate 2 was added and dissolved in 10 mL of tetrahydrofuran. After the ice bath was complete, 1.12 g of nitrogen bromosuccinimide was added, and the mixture was reacted for 30 min under magnetic stirring, and the reaction was detected by TLC. Add 20 mL of water, extract the reaction mixture with chloroform, combine the organic phases, dry the organic phases with anhydrous sodium sulfate, filter off the desiccant, and spin dry the solvent. The white solid powder obtained is directly used in the next reaction.

[0084] In a dry Schlenk reaction flask, add 600 mg of the product obtained in the above reaction, and then add 1.614 g of 4-methyl-N-(4-methylphenyl)-N-(4-(4,4,5,5-tetra Methyl-1,3,2-dioxaborolan-2-yl)phenyl)amine, 1.43g potassium phosphate, then add 20mL dioxane, 4mL water to dissolve, add 7.26mg Pd( OAC) 2 13...

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Abstract

The invention provides a thiophene compound, a preparation method and application thereof and a perovskite solar battery. The thiophene compound is shown in a formula (I), R1 and R1' are independently H, C1-C12 alkyls or C1-C12 alkoxyls respectively, and R2, R3 and R4 are independently H, C1-C12 alkyls, C1-C12 alkoxyls or C1-C12 alkoxyl substituted phenyls respectively. Compared with the prior art, the thiophene compound is of a structure that dithienothiophene, thieno pyrrole or dithieno cyclopentadiene is conjugated and coupled with two triarylated amine, so that the hole mobility of the compound is high, and further the perovskite solar battery of a hole transportation layer prepared from the thiophene compound has high energy conversion efficiency.

Description

technical field [0001] The invention belongs to the technical field of perovskite solar cells, and in particular relates to a thiophene compound, a preparation method and application thereof, and a perovskite solar cell. Background technique [0002] In 2009, organic-inorganic hybrid perovskites were first applied in solar cells as light-absorbing materials. After 2012, the reports on this new type of solar cell showed a blowout growth, and by 2016 the energy conversion efficiency of 22.1% was achieved, exceeding 1cm 2 The device achieved an energy conversion efficiency of 19.6% (Science, 2016, 353, 58-62). At the same time, solution-processed perovskite solar cells can achieve high efficiency and large-scale mass production through roll-to-roll. Compared with traditional silicon-based solar cells, the manufacturing cost is low, the processing technology is simple, and it has good commercial prospects. . [0003] 2,2′,7,7′-Tetrakis[N,N-bis(4-methoxyphenyl)amino]-9 is the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/14C07D409/04H01L51/46H01L51/48
CPCC07D409/04C07D495/14H10K85/631H10K85/6576H10K30/20Y02E10/549
Inventor 王鹏王俊婷李阳董献堆
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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