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Solution-processable two-dimensional conjugated organic molecule photovoltaic material, preparation method and application thereof

A reaction and carbon atom technology, applied in photovoltaic power generation, organic chemistry, semiconductor/solid-state device manufacturing, etc., can solve problems such as low hole mobility, low filling factor of photovoltaic devices, weak interaction, etc.

Active Publication Date: 2014-05-14
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

However, due to the non-planarity of triphenylamine, the interaction between molecules is weak, resulting in lower hole mobility and lower filling factor of photovoltaic devices, which limits the efficiency of photovoltaic devices.

Method used

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  • Solution-processable two-dimensional conjugated organic molecule photovoltaic material, preparation method and application thereof
  • Solution-processable two-dimensional conjugated organic molecule photovoltaic material, preparation method and application thereof
  • Solution-processable two-dimensional conjugated organic molecule photovoltaic material, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1, the synthesis of α-Bromine β-hexylthienylvinindanone (in the formula III, R 3 =C 6 h 13, n=1 compound)

[0034] With 3.03g of indanone (formula IV), 6.25g of compound (formula V, n=1, R 3 =C 6 h 13 ), 2ml of piperidine and 22.8ml of dried acetonitrile were added to the reactor for mixing and dissolving, and then refluxed at 80° C. for 24 hours under the protection of nitrogen. The reaction mixture was cooled to room temperature, then dissolved in dichloromethane, washed with brine, dried over anhydrous magnesium sulfate, evaporated the solvent in vacuo, and washed with dichloromethane / petroleum ether (1 / 5, V / V) Purified by chromatographic column to obtain 5 g of yellow solid α-Bromine β-hexylthienylvinindanone, yield: 60%. GC / MS: 402 (M+).

[0035] The structural confirmation data are as follows: 1 H NMR (400MHz, CDCl 3 )δ (ppm): 7.96-7.95 (t, 2H), 7.835 (s, 1H), 7.81-7.77 (m, 2H), 7.599 (s, 1H), 2.64-2.60 (t, 2H), 1.66-1.58 (m, 3H), 1.38-1.25 (m...

Embodiment 2

[0036] Embodiment 2, the synthesis of α-Bromine β-hexyl dithienylvinindanone (in the formula III, R 3 =C 6 h 13 , n=2 compounds)

[0037] With 1.34g of indanone (formula IV), 4.0g of compound (formula V, n=2, R 3 =C 6 h 13 ), 2ml of piperidine and 22.8ml of dried acetonitrile were added to the reactor for mixing and dissolving, and then refluxed at 80° C. for 24 hours under the protection of nitrogen. The reaction mixture was cooled to room temperature, then dissolved in dichloromethane, washed with brine, dried over anhydrous magnesium sulfate, evaporated the solvent in vacuo, and washed with dichloromethane / petroleum ether (1 / 5, V / V) Purified by chromatographic column to obtain 5 g of yellow solid α-Bromine β-hexyldithiophene vinylindanone, yield: 60%. MALDI-TOF: MS: 569.1, calculated for C 30 h 33 BrO 2 S 2 The mass-to-charge ratio is 569.62.

[0038] The structural confirmation data are as follows: 1 H NMR (400MHz, CDCl 3 )δ (ppm): 8.09-8.07 (s, 1H), 7.97-7.94...

Embodiment 3

[0039] Embodiment 3,2,6-dithiophene vinyl indanone 4,8-dithiophene benzo [1,2-b:4,5-b'] synthesis of dithiophene (TVIBDT-T) (in the formula I, R 1 = R 3 =C 6 h 13 , R 2 =H, the compound of n=1)

[0040] Add 0.523g monomer formula II, 0.5g monomer α-Bromine β-hexylthienylvinindanone and 20mL toluene to a 50mL three-necked flask, and after 15 minutes of passing nitrogen, add 30mg tetrakis(triphenylphosphine) palladium ( 0.026mmol), the temperature was raised to 115°C and the reaction was stirred for 24 hours. After the reaction was completed, it was cooled to room temperature, and the reaction solution was settled in 200 mL of methanol, and then filtered with suction to collect a black solid. Then adopt dichloromethane / petroleum ether (1 / 1, v / v) to separate and purify the product through a chromatographic column to obtain 0.575 g of black molecular TVIBDT-T solid, with a yield of 80%. MALDI-TOF: m / z 1166.6. Calculated C 70 h 70 o 4 S 6 The mass-to-charge ratio is 1166....

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Abstract

The present invention discloses a solution-processable organic molecule photovoltaic material based on two-dimensional conjugated benzodithiophene, a preparation method and an application thereof. According to the present invention, the molecules adopt thiophene substituted two-dimensional conjugated benzodithiophene as a core, both terminals are symmetrically connected with a thienylethene indene or bithienylethene indene conjugated structure unit, the structure formula is represented by a formula I, the molecules have good dissolubility in common organic solvents (such as dichloromethane, trichloromethane, tetrahydrofuran and the like), and the high-quality film can be prepared by using the solution method; compared with the polymer material, the material of the present invention is easy to purify, and the high purity material can be obtained; and the organic molecules are used for the donor material of organic solar cells, wherein the energy conversion efficiency is more than 6.5%. (Formula I).

Description

technical field [0001] The invention relates to a solution-processable two-dimensional conjugated organic molecular photovoltaic material and its preparation method and application. Background technique [0002] In 1986, Dr. Deng Qingyun of Kodak Company used copper phthalocyanine as the donor (D) and perylene as the acceptor (A) to prepare an organic photovoltaic device with a D / A heterojunction double-layer structure (C.W.Tang, Appl.Phys. Lett., 1986, 48: 183-185.), the energy conversion efficiency is close to 1% under simulated sunlight. In 1995, Yu Gang and others in Haig's research group invented a solution-processable conjugated polymer / soluble C 60 Derivative blend type "bulk heterojunction" (bulk heterojunction) polymer solar cell (G. Yu J. Gao J. C. Hummelen, F. Wudl, A. J. Heeger, Science, 1995, 270: 1789-1791.). The bulk heterojunction solar cell simplifies the preparation process, improves the energy conversion efficiency by enlarging the donor-acceptor interfa...

Claims

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Application Information

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IPC IPC(8): C07D495/04H01L51/46C07D333/28
CPCC07D333/28C07D495/04H10K85/655H10K85/626H10K85/6576Y02E10/549
Inventor 李永舫申素玲江培何畅
Owner INST OF CHEM CHINESE ACAD OF SCI
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