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Organic solar cell material containing triphenylamine-thiophene structure and its synthesis method

A technology of solar cells and triphenylamine, applied in the direction of organic chemistry, etc., can solve the problems of reducing the efficiency of charge separation, low efficiency of Schottky cells, etc., and achieve the effect of simple synthesis process

Inactive Publication Date: 2015-11-25
XI AN JIAOTONG UNIV
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  • Description
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Problems solved by technology

However, the efficiency of the Schottky cell made of a pure organic compound sandwiched between two layers of metal electrodes is very low. Later, the p-type semiconductor material (donor, hereinafter referred to as D) and n-type Semiconductor materials (Acceptor, hereinafter abbreviated as A) recombine, and it is found that the dissociation of electron-hole pairs at the interface of the two materials is very effective, and the luminescent recombination and deactivation process of the photoexcited unit is effectively inhibited, resulting in efficient charge separation
[0005] Traditional D-A type composite materials mainly include double-layer membrane system, blended membrane system and laminated membrane system, but the interpenetrating bicontinuous network structure with micro-phase separation obtained by physical composite means, this structure has great influence on the morphology of the composite membrane. It is very sensitive, and the membrane produced has certain structural defects, and sometimes there will be two-phase separation regions, thereby reducing the charge separation efficiency.

Method used

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  • Organic solar cell material containing triphenylamine-thiophene structure and its synthesis method
  • Organic solar cell material containing triphenylamine-thiophene structure and its synthesis method
  • Organic solar cell material containing triphenylamine-thiophene structure and its synthesis method

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Embodiment 1

[0085] What this embodiment synthesizes is the organic solar cell material containing triphenylamine-thiophene structure, and its molecular formula is C 154 h 182 N 4 o 4 P 4 Pt 2 S 12 , whose structural formula is (I–a):

[0086]

[0087] Its synthetic method comprises the following steps:

[0088] Step 1: Obtain R1 according to the synthesis method of the bridging unit R1 of the above-mentioned π-conjugated structure;

[0089] Step 2: Obtain G according to the specific synthesis route of the above-mentioned organometallic aryne ligand containing the triphenylamine-thiophene structure;

[0090] Step 3: Weigh 0.15g (0.21mmol) R1 into a 100mL three-necked flask, add 50mL of a mixed solution of dichloromethane and triethylamine (V:V=1:1), and add 10% mol of iodide under nitrogen atmosphere Cuprous, then added 0.64g (0.53mmol) of G, stirred at room temperature and maintained the reaction for 2 hours. Concentrated and separated by thin-layer chromatography to obtain 0....

Embodiment 2

[0092] What this embodiment synthesizes is the organic solar cell material containing triphenylamine-thiophene structure, and its molecular formula is C 166 h 182 N 12 P4 Pt 2 S 12 , whose structural formula is (I–b):

[0093]

[0094] Its synthesis method is the same as that of Example 1, except that in step 3, add 0.20 g (0.066 mmol) of the obtained aldehyde-containing battery material I-a into a 100 mL one-necked bottle, add 40 mL of dichloromethane to completely dissolve it, and then add 35 mg (0.53 mmol) of malononitrile and 5 drops of triethylamine were stirred at room temperature for reaction, detected by TLC until the end of the reaction; concentrated, chromatographed with methanol and washed several times to finally obtain 0.20 g of dark red solid with a yield of 94.1% , according to NMR analysis, the product is a cyano-containing battery material I–b: 1 HNMR (400MHz, CDCl 3 ):δ(ppm)7.78(s,4H),7.70(d,J=3.2Hz,4H),7.61(d,J=8.4Hz,8H),7.51(d,J=8.0Hz,4H),7.38 (d,...

Embodiment 3

[0096] What this embodiment synthesizes is the organic solar cell material containing triphenylamine-thiophene structure, and its molecular formula is C 156 h 190 N 2 o 4 P 4 Pt 2 S 11 , whose structural formula is (I–c):

[0097]

[0098] Its synthesis method is the same as that of Example 1, the only difference being that the π-conjugated Overseas Chinese Union unit with R2 structure is used in Step 1.

[0099] NMR analysis data: 1 HNMR (400MHz, CDCl 3 ):δ(ppm)9.88(s,4H),7.73(d,J=3.6Hz,4H),7.58(d,J=8.4Hz,8H),7.49(d,J=8.4Hz,4H),7.34 (d,J=3.6Hz,4H),7.17(d,J=8.4Hz,8H),7.13(d,J=8.0Hz,4H),7.07(d,J=3.6Hz,2H),7.03(d ,J=3.6Hz,2H),7.00(d,J=3.6Hz,2H),6.96(d,J=3.2Hz,2H),6.81(d,J=3.6Hz,2H),6.74(d,J =3.6Hz,2H),2.70(m,4H),2.12-2.11(m,24H),1.60-1.59(m,24H),1.53-1.44(m,24H),1.28(m,16H),0.95( t,J=7.2Hz,36H),0.88(m,6H); 13 CNMR (100MHz, CDCl 3 ):δ(ppm)182.67,153.99,147.96,144.98,141.74,140.17,139.90,137.66,134.31,133.63,131.07,129.76,128.44,128.04,127.60,127.48,126.54,126.24,1...

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Abstract

The invention relates to an organic solar cell material having a triphenylamine-thiophene structure, and a synthetic method thereof. The material has a triphenylamine-thiophene structure, and is an organic metallic aryne functional material having a D-A structure. The synthetic method comprises the following steps: 1, synthesizing a bridged unit having a pi conjugate structure; 2, synthesizing an organic metallic aryne ligand having a triphenylamine-thiophene structure; and 3, mixing a product obtained in step 1 and a product obtained in step 2, synthesizing an aldehyde-containing organic solar cell material through a Sonogashira coupling reaction by using cuprous iodide as a catalyst, reacting an aldehyde product with malononitrile, and carrying out an addition reaction under the catalysis of weakly alkaline solvents comprising triethylamine and the like for introducing a cyan group. The material has a strong absorption capability in a visible light range and is helpful for improving the absorption rate of photoelectric devices to sunlight, so the photoelectric conversion efficiency is improved. The material also has a good film forming performance and a good dissolvability, has a simple preparation technology, and is in favor of improving the photoelectric conversion efficiency of a solar cell.

Description

technical field [0001] The invention belongs to the field of organic photoelectric materials and relates to the preparation of a novel organic solar cell material, in particular to an organic solar cell material containing a triphenylamine-thiophene structure and a synthesis method thereof. Background technique [0002] As the global energy demand increases year by year, the reserves of traditional energy such as coal, oil, and natural gas are decreasing day by day, and the effective use of renewable energy has become an urgent problem to be solved. Solar energy, which accounts for more than 99% of the earth's total energy, is inexhaustible, inexhaustible, and non-polluting, so it has become one of the new energy sources developed and utilized by scientists from all over the world. Especially for solar cells made of organic semiconductor materials, due to the wide variety of organic compounds, the chemical structure of organic molecules is easy to modify, the preparation and...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F19/00
Inventor 周桂江姚纯亮黄躜
Owner XI AN JIAOTONG UNIV
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