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Novel organic conjugated molecule and application thereof in organic solar cell

A conjugated molecular and organic technology, applied in the field of solar cells, to achieve the effect of convenient purification, high open circuit voltage, and simple synthesis method

Inactive Publication Date: 2013-03-20
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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  • Novel organic conjugated molecule and application thereof in organic solar cell
  • Novel organic conjugated molecule and application thereof in organic solar cell
  • Novel organic conjugated molecule and application thereof in organic solar cell

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1: Synthesis of APD

[0046] Put 278 mg of triphenylamine aldehyde and 142 mg of 5-(2,6-bis((E)-4-(diphenylamine)styrene-4H-pyran-4-ylidene)-1 in a round bottom flask, 3-Diethyl-2-thioketo-dihydropyrimidine-4,6(1H,5H)-dione and 0.5 ml piperidine, add 20 ml of acetonitrile, stir to dissolve. Heat to 90 under nitrogen After reacting for 12 hours at ℃, pour into water and extract with dichloromethane, combine the organic solvents, wash with saturated brine, and then dry with anhydrous magnesium sulfate. Remove the solvent, the ratio of petroleum ether: dichloromethane 1:3 is taken as Developing solvent, silica gel as stationary phase, purified by column chromatography to obtain 2-(2,6-bis((E)-2-(5-bromo-3,4-dihexanethiophene-2 ​​vinyl)) -4H-pyran-4-ylidene)-1,3-diethyl-2-thioketo-dihydropyrimidine-4,6(1H,5H)-dione (TDT) 298 mg.

[0047] 1 H NMR (500MHz, CDCl3, TMS): δ (ppm) 8.909 (s, 2H, -PD), 7.518 (d, 2H, J=15.6 Hz, -vinylic), 7.422 (d, 4H, -TPA), 7.318 (t, 8H, -TP...

Embodiment 2

[0049] Example 2: Synthesis of PhPD

[0050] The synthesis of PhPD is the same as in Example 1. Just use 10-octyl-10H-phenothiazine-3-carbaldehyde instead of triphenylamine aldehyde. Yield: 80.3%.

[0051] 1 H NMR(500MHz, CDCl 3 , TMS): δ (ppm) 8.914 (s, 2H, -PD), 7.441 (d, 2H, J=15.6Hz, -vinylic), 7.364 (d, 2H, -Ph), 7.321 (s, 2H,- Ph), 7.150 (m, 4H, -Ph), 6.950 (t, 2H, -Ph), 6.868 (t, 2H, -Ph), 6.771 (d, 2H, J=15.6 Hz, -vinylic), 4.612 ( m, 4H, -CH 2 ), 3.875(t, 4H, -CH 2 ), 1.826(m, 4H, -CH 2 ), 1.453(m, 4H, -CH 2 ), 1.290(m, 22H, -CH 2 , -CH 3 ), 0.876(t, 6H, -CH 3 ),. Elemental analysis according to chemical formula C 57 H 64 N 4 O 3 S 3 Calculation: C, 72.11; H, 6.80; N, 5.90; O, 5.06; S, 10.13. Experimental value: C, 72.04; H, 6.82; N, 5.93; O, 5.03; S, 10.16. Its structural formula is as follows,

[0052]

Embodiment 3

[0053] Example 3: Synthesis of CZPD

[0054] The synthesis of PhPD is the same as in Example 1. Just use 9-octyl-9H-carbazole-3-carbaldehyde instead of triphenylamine aldehyde. Yield: 80.3%.

[0055] 1 H NMR(300MHz, CDCl 3 , TMS): δ (ppm) 8.908 (s, 2H, -PD), 8.312 (d, 2H, -CZ), 8.153 (d, 2H, -CZ), 7.798 (d, 2H, J = 15.9 Hz,- vinylic), 7.737 (m, 2H, -CZ), 7.520 (m, 2H, -CZ), 7.428 (d, 2H, -CZ), 7.428 (d, 2H, -CZ), 7.401 (d, 2H,- CZ), 7.308 (t, 2H, -CZ), 6.952 (d, 2H, J=15.9 Hz, -vinylic), 4.585 (m, 4H, -CH 2 ), 4.277(t, 4H, -CH 2 ), 1.885(m, 4H, -CH 2 ), 1.331(m, 26H, -CH 2 , -CH 3 ), 0.874(t, 6H, -CH 3 ), elemental analysis according to chemical formula C 53 H 56 N 4 O 3 S calculation: C, 76.78; H, 6.81; N, 6.76; O, 5.79; S, 3.87. Experimental value: C, 76.75; H, 6.84; N, 6.74; O, 5.71; S, 3.90. Its structural formula is as follows,

[0056]

[0057] Synthesis of organic conjugated small molecules of general formula (III):

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Abstract

The invention belongs to the technical field of solar cells and particular relates to a donor-acceptor organic conjugated molecule taking 5-(2,6-dimethyl-4H-pyran-4-ylene)-1,3-diethyl-2-thioxo-dihydro-pyrimidin-4,6(1H,5H)-diketone as an acceptor and the application of the organic conjugated molecule to a bulk heterojunction solar cell. A series of different donor units is coupled with the 5-(2,6-dimethyl-4H-pyran-4-ylene)-1,3-diethyl-2-thioxo-dihydro-pyrimidin-4,6(1H,5H)-diketone so as to obtain a donor-acceptor organic conjugated molecule solar cell material with a low highest occupied molecular orbital (HOMO) energy level (high open circuit voltage and high stability), a narrow band gap and wide absorption. The organic conjugated molecule is used for preparing the solar cell, so that a device with a high open circuit voltage and high photoelectric conversion efficiency can be obtained.

Description

Technical field [0001] The invention belongs to the technical field of solar cells, and specifically relates to a class of 5-(2,6-dimethyl-4H-pyran-4-ylidene)-1,3-diethyl-2-thioketo-di Hydropyrimidine-4,6(1H,5H)-dione is the basic structural unit of donor and acceptor organic conjugated molecules and the application of the organic conjugated molecules in bulk heterojunction solar cells. Background technique [0002] With the gradual depletion of primary energy sources such as coal and petroleum, mankind urgently needs environmentally friendly renewable energy. Solar cells can directly convert solar energy into electricity and are the most effective way to utilize solar energy. [0003] In 1954, Bell Labs in the United States successfully developed the first monocrystalline silicon solar cell, opening a door for mankind to use solar energy to generate electricity. In 1958, solar cells were first used in spacecraft. In the early 1970s, solar cells began to be applied on the ground...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/04C07D409/14C07D417/14C07D405/14H01L51/46
CPCY02E10/50Y02E10/549
Inventor 田文晶李在房董庆锋徐斌
Owner JILIN UNIV