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A kind of soluble thiophene copolymer with electron-withdrawing group and its preparation method and application

An electron-withdrawing-based, copolymer technology, applied in circuits, photovoltaic power generation, electrical components, etc., can solve the problems of inferior, limited application of P3HT, general solubility, etc., achieve high efficiency, excellent hole transport performance, and improve air stability. sexual effect

Active Publication Date: 2021-11-19
EAST CHINA NORMAL UNIV +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The energy level of P3HT has the best match with perovskite solar cells (-5.20eV), and it is currently a polymer material commonly used in the hole transport layer of perovskite cells, but its solubility is average (0.1mg / mL), which is far from It is not as good as the traditional hole transport material small molecule spiro-OMeTAD, which limits the application of P3HT to a certain extent

Method used

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  • A kind of soluble thiophene copolymer with electron-withdrawing group and its preparation method and application
  • A kind of soluble thiophene copolymer with electron-withdrawing group and its preparation method and application
  • A kind of soluble thiophene copolymer with electron-withdrawing group and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0144] Preparation of monomethyl ether diethoxyethyl thiophene carboxylate (MECT)

[0145] The synthetic process is shown in route (1'):

[0146]

[0147] Among them, R 1 It is 2-(2-(2-methoxyethoxy)ethoxy)ethyl carboxylate, abbreviated as MPEG-3OOC, and the ester bond -COO- is a strong electron-withdrawing group.

[0148] The specific synthesis steps are as follows:

[0149] N 2 To a purified three-necked round-bottom flask, add 300 mL of redistilled dichloromethane (DCM), 5.19 g (40.5 mmol, 1.0 equivalents) of 3-thiophenecarboxylic acid (TCA), 2-(2-( 2-methoxyethoxy) ethoxy) ethanol (2-(2-(2-methoxyethoxy)ethoxy)ethanol) 6.65g (6.5mL, 40.5mmol, 1.0 equivalent) and esterification catalyst 4-dimethylaminopyridine (DMAP) 7.40 g (60.5 mmol, 1.5 equiv). The reactant was colorless, clear and transparent, and was stirred at room temperature for 1 h. then cooled to 0°C in N 2 9.19 g (44.5 mmol, 1.1 equivalents) of dicyclohexylcarbodiimide (DCC) was added under atmosphere. ...

Embodiment 2

[0153] Preparation of monomer 3-heptyloxythiophene (HPOT)

[0154] Synthesis is shown in route (2'):

[0155]

[0156] Among them, R 3 For heptyloxy.

[0157] The specific synthesis steps are as follows:

[0158] After adding CuI 11.20g (58.80mol, 0.20 equivalents), potassium tert-butoxide tBuOK49.60g (442.0mols, 1.50 equivalents), n-heptanol 83.24mL (588.8mols, 2.00 equivalents) in a 500mL round bottom flask, Pure N 2 The round bottom flask was purged and stirred at room temperature for 1 h. Add 27.60 mL (294.4 mol, 1.00 equivalent) of 3-bromothiophene (substance 1), reaction temperature: 100° C., reaction time: 24 h. Cool to room temperature after the reaction.

[0159] Refining method: the mixture was washed with tetrahydrofuran (THF), filtered to remove most of the inorganic salts, the filtrate was collected, and 44.44 g of a light yellow oily liquid product 3-heptyloxythiophene (HPOT) was obtained by distillation under reduced pressure, with a yield of 76.12%.

...

Embodiment 3

[0162] Preparation of poly(monomethyl ether diethoxyethylthiophene carboxylate / 3-hexylthiophene) P(MECT-3HT)

[0163] Synthesis is shown in route (3'):

[0164]

[0165]

[0166] Among them, R 1 It is 2-(2-(2-methoxyethoxy)ethoxy)ethyl carboxylate, abbreviated as MPEG-3OOC, and the ester bond -COO- is a strong electron-withdrawing group; R 2 For hexyl.

[0167] In this example, the prepared thiophene copolymer poly(monomethyl ether diethoxyethyl thiophene carboxylate / 3-hexylthiophene) P(MECT-3HT) has a thiophene chain as the core, and at its β-position Electron-withdrawing group MPEG-3OOC and hexyl side chain, the structural formula is shown in formula (A),

[0168]

[0169] The general formula is shown in the following formula (X):

[0170]

[0171] Among them, in formula (X), R 1 The ester bond is a strong electron-withdrawing group; a=3, b=5, c=6; R 4 =-CH 3 ; x=2.9, y=34.8, z=0.

[0172] Due to FeCl 3 If it is not removed, Fe will be generated 2 o 3 ...

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Abstract

The invention discloses a soluble thiophene copolymer with an electron-withdrawing group, which comprises poly(monomethyl ether diethoxyethyl thiophene carboxylate / 3‑hexylthiophene) (P(MECT‑3HT)), poly(monomethyl ether diethoxyethylthiophene carboxylate / 3‑heptyloxythiophene) (P(MECT‑HPOT)) and poly(monomethyl ether Ether diethoxyethylthiophene carboxylate / 3‑heptyloxythiophene / 3‑hexylthiophene) (P(MECT‑HPOT‑3HT)), its molecular structure is simple, heptyloxy, hexyl can be introduced into the side group etc., have the characteristics of high hole mobility, high efficiency, high conductivity and good solubility. The invention also discloses the preparation method of the soluble thiophene copolymer with electron-withdrawing groups, using FeCl 3 As a catalyst, it is obtained through one-step chemical oxidation polymerization. The preparation method of the invention has the characteristics of simple operation, cheap and readily available raw materials and catalysts, and easy separation. The invention also discloses that the soluble thiophene copolymer with electron-withdrawing groups can be applied to prepare perovskite solar cell hole transport materials and perovskite solar cell copolymers, which can match the energy level of perovskite.

Description

technical field [0001] The invention belongs to the technical field of chemistry and energy battery materials, and specifically relates to a soluble thiophene copolymer with an electron-withdrawing group and its preparation method and application. Background technique [0002] Hole-transporting materials have many uses, such as electroluminescent devices such as light-emitting diodes (LEDs), polymer solar cells, dye-sensitized solar cells, and perovskite solar cells. After the first generation of silicon solar cells, the second generation of III B After the development of thin-film solar cells such as group VIII compounds and copper indium gallium selenide (CIGS) and third-generation organic thin-film and dye-sensitized solar cells, perovskite solar cells (Perovskite Solar Cell, PSC) have emerged as a new force and become a research hotspot. Perovskite solar cells have the advantages of simple material synthesis, convenient preparation process, high solar absorption rate, a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/46
CPCC08G61/126C08G2261/1424C08G2261/1426C08G2261/124C08G2261/3223C08G2261/91C08G2261/18C08G2261/512C08G2261/64H10K85/1135Y02E10/549
Inventor 蒋兰兰陆曼王鑫亮宋春梅黄宇雯宋全安万波
Owner EAST CHINA NORMAL UNIV
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