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Organic conjugated molecule capable of being processed by solution and application thereof in solar cells

A technology of solar cells and conjugated molecules is applied in the field of solar cells to achieve the effects of high photoelectric conversion efficiency, low HOMO energy level and simple preparation process

Inactive Publication Date: 2010-07-28
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, compared with organic polymer solar cells, organic small molecule solar cells still have many shortcomings.

Method used

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  • Organic conjugated molecule capable of being processed by solution and application thereof in solar cells
  • Organic conjugated molecule capable of being processed by solution and application thereof in solar cells
  • Organic conjugated molecule capable of being processed by solution and application thereof in solar cells

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Experimental program
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Effect test

Embodiment 1

[0034] Embodiment 1: the synthesis of 4TPM

[0035]Put magnesium chips (5.76 g, 0.24 mol) and 20 ml of dry diethyl ether into a three-neck flask to mix, and cool to 0°C. n-Bromohexane (44 ml, 0.312 mol) was added dropwise to the mixed solution, and after the dropwise addition was completed, it was refluxed at 50° C. for 2 hours until the reaction of Mg was complete. Then the reaction temperature was cooled to room temperature, and 1,3-bis(diphenylphosphinopropane)nickel dichloride Ni(dppp)Cl 2 (240 mg, 0.367 mmol) was added to the reaction solution, and 3,4-dibromothiophene (11.36 ml, 0.1 mol) was added dropwise to the solution. After the dropwise addition, react at 50°C for 24h. The reactant was poured into water and extracted with ether, the organic solvents were combined, washed with saturated brine, and then dried over anhydrous magnesium sulfate to remove the solvent. Using petroleum ether as a developing solvent and silica gel as a stationary phase, 18.9 g of light ye...

Embodiment 2

[0042] Embodiment 2: the synthesis of 6TPM

[0043] The synthesis of 6TPM is the same as in Example 1. Only 2,2'-dithiophene-5-tributyltin is used instead of 4,4,5,5-tetramethyl-2-thiophene-1,3,2-dioxaboron. Yield: 80.3%.

[0044] 1 H NMR (500MHz, CDCl3, TMS): δ (ppm) 7.608 (d, 2H, J = 15.6Hz, -vinylic), 7.269 (s, 2H, -Th), 7.224 (d, 2H, -Th), 7.167 (d, 2H, -Th), 7.136 (d, 2H, -Th), 7.054 (m, 2H, -Th), 6.618 (s, 2H, -PM), 6.473 (d, 2H, J=15.3Hz, -vinylic), 2.730(m, 8H, -CH2), 1.573(m, 8H, -CH2), 1.445(m, 8H, -CH2), 1.332(m, 16H, -CH2), 0.921(m, 6H, -CH3), 0.859(m, 6H, -CH3). 13 C NMR(75MHz,CDCl3,TMS):δ(ppm)140.273,138.264,136.727,134.399,134.067,133.136,128.196,127.946,124.904,124.590,124.101,123.966,116.411,115.416,106.503,58.901,31.675,31.610, 31.460, 30.334, 29.500, 29.499, 27.965, 27.721, 22.619, 22.585, 14.015, 13.969. Mass spectrum calculation formula C 60 h 68 N 2 OS 6 Obtain 1025.58; experimental value: 1025.70. Its structural formula is as follows:

[0045]...

Embodiment 3

[0046] Embodiment 3: the synthesis of 8TPM

[0047] The synthesis of 8TPM is the same as in Example 1. Just replace 4,4,5,5-tetramethyl-2-thiophene-1,3,2-dioxabor with 2,2:5,2-trithiophene-5-trimethyltin-trimethyltin . Yield: 72.6%.

[0048] 1 H NMR (500MHz, CDCl3, TMS): δ (ppm) 7.601 (d, 2H, J = 15.6Hz, -vinylic), 7.252 (m, 2H, -Th), 7.202 (m, 2H, -Th), 7.134 (m, 8H, -Th), 7.042 (m, 2H, -Th), 6.605 (s, 2H, -PM), 6.460 (d, 2H, J=15.3Hz, -vinylic), 2.733 (m, 8H, -CH2), 1.587(m, 8H, -CH2), 1.460(m, 8H, -CH2), 1.323(m, 16H, -CH2), 0.927(m, 6H, -CH3), 0.864(m, 6H, -CH3). 13 C NMR(75MHz,CDCl3,TMS):δ(ppm)158.021,155.199,147.211,147.119,140.325,137.928,136.925,136.888,135.445,134.542,134.048,133.028,128.167,127.923,127.294,124.717,124.571,124.419, 124.035, 123.883, 116.482, 106.558, 58.964, 31.696, 31.638, 31.493, 30.334, 29.688, 29.537, 29.482, 28.033, 27.746, 22646, 14.050, 13.992 C. Mass spectrum calculation 68 h 72 N 2 OS 8 Obtain 1189.83; experimental value: 1189.20. ...

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Abstract

The invention, which belongs to the technical field of solar cells, relates to a donor-acceptor type organic conjugated molecule based on 2-pyran-4-ylidene malononitrile as acceptor and the application of the organic conjugated molecule in bulk heterojunction solar cells. The invention provides a series of low-HOMO energy level (high open circuit voltage and high stability), narrow-bandgap, high-absorbability and high-mobility donor-acceptor type organic conjugated molecule solar cell materials by selecting different donor units to couple with 2-pyran-4-ylidene malononitrile (acceptor unit); when the organic conjugated molecule is used in the production of solar cells, an element with a high open circuit voltage and high photoelectric conversion efficiency can be obtained; and moreover, the element production technique is simple, can be easily repeated, and is favorable for the industrialized batch production of elements.

Description

technical field [0001] The invention belongs to the technical field of solar cells, and specifically relates to an organic conjugated molecule based on 2-pyran-4-ylidenedicyanide as a basic structural unit and the application of the organic conjugated molecule in bulk heterojunction solar cells . Background technique [0002] With the gradual depletion of primary energy such as coal and oil, human beings urgently need environmentally friendly renewable energy. Solar cells convert solar energy directly into electricity and are the most efficient way to utilize solar energy. [0003] In 1954, Bell Laboratories in the United States successfully developed the first monocrystalline silicon solar cell, which opened a door for human beings to use solar power to generate electricity. In 1958, solar cells were first applied on spacecraft. In the early 1970s, solar cells began to be applied on the ground. However, the preparation process is complicated, the cost is high, and the e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/14C07D409/14C07D309/34C07D405/14H01L51/42H01L51/46
CPCY02E10/50Y02E10/549Y02P70/50
Inventor 田文晶李在房徐斌李耀文裴佳宁
Owner JILIN UNIV
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