All-conjugate side-chain polymer and application thereof in polymer solar devices

A technology of conjugating side chains and polymers is applied in the field of organic polymer semiconductor materials, which can solve the problems of low carrier mobility and low matching degree of active layers, and achieve the effect of good performance and high efficiency.

Inactive Publication Date: 2013-06-19
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Studies have found that the main factors restricting the efficiency of polymer solar cells are the poor matching between the absorption spectrum of the active layer and the solar spectrum, and the low carrier mobility of organic materials.

Method used

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  • All-conjugate side-chain polymer and application thereof in polymer solar devices
  • All-conjugate side-chain polymer and application thereof in polymer solar devices
  • All-conjugate side-chain polymer and application thereof in polymer solar devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Preparation of 1,3-dibromo-5-(4-octylphenyl)-5H-thiophene-[3,4-c]-pyrrole-3,6-dione, whose structural formula is:

[0041] .

[0042] Add 1.50 g of 4,6-dibromo-thiophene-[3,4-c]furan-1,3-dione, 0.44 g of 4-octylaniline and 0.72 g of 4-dimethylaminopyridine into a 100 mL flask, Add 35 ml of anhydrous 1,4-dioxane, stir and react for 20 hours under the protection of argon at 60°C, add 20 ml of glacial acetic acid, heat up to 80°C and continue stirring for 4 hours, pour into water after cooling, and use dichloro After extraction with methane, the organic layer was dried with anhydrous sodium sulfate and spin-dried, passed through the column with dichloromethane / petroleum ether = 1:5, and spin-dried to obtain 0.65 g of the target compound, with a yield of 61.4%. 1 H NMR (400 MHz, CDCl 3 ) δ (ppm): 7.28 (d, 2H), 7.23 (d, 2H), 2.63 (t, 2H), 1.62 (m, 2H), 1.36 – 1.29 (m, 10H), 0.88 (t, 3H), 13 C NMR (100 MHz, CDCl 3 ) δ (ppm): 155.9, 153.1, 149.4, 149.1, 148.7, 141.8...

Embodiment 2

[0047] Polymer poly{[4,8-bis(5-(2-ethylhexyl)-thienyl)-benzo[1,2-b;4,5-b']dithieno-co-1, Synthesis of 3-dibromo-5-(4-octylphenyl)-5H-thiophene-[3,4-c]-pyrrole-3,6-dione (polymer PBDT-TT-P-TPD), Synthetic route such as figure 2 shown.

[0048] .

[0049] Take 0.24 g of 4,6-bis(trimethyltinyl)-4,8-bis(5-(2-ethylhexyl)-thienyl)-benzo[1,2-b;4,5- b']dithiophene, 0.12 g of 1,3-dibromo-5-(4-octylphenyl)-5H-thiophene-[3,4-c]-pyrrole-3,6-dione was added to 50 ml of reaction In the tube, add catalyst 0.01 g tris(dibenzylideneacetone) dipalladium, ligand 0.02 g tri-o-methylphenylphosphine, add 5 ml anhydrous toluene, 0.5 ml anhydrous N,N-dimethylformamide , stirred and reacted for 48 hours in an argon atmosphere at 110°C. Cool the polymer to room temperature and slowly pour it into 70 ml of methanol. The precipitated polymer is filtered and washed with methanol and n-hexane successively in a Soxhlet extractor. Finally, it is dissolved in chloroform and precipitated into methanol,...

Embodiment 3

[0051] Polymer poly{[4,8-bis(5-(2-ethylhexyl)-thienyl)-benzo[1,2-b;4,5-b']dithieno-co-1,3 -Synthesis of dibromo-5-(4-octylphenyl)-5H-thiophene-[3,4-c]-pyrrole-3,6-dione (polymer PBDT-T-P-TPD), the synthetic route is as follows image 3 shown.

[0052] .

[0053] Take 0.21 g of 4,6-bis(trimethylstannyl)-4,8-bis(5-(2-ethylhexyl)-thienyl)-benzo[1,2-b;4,5-b ']dithiophene, 0.12 g of 1,3-dibromo-5-(4-octylphenyl)-5H-thiophene-[3,4-c]-pyrrole-3,6-dione into a 50 ml reaction tube Add catalyst 0.01 g tris(dibenzylideneacetone) dipalladium, ligand 0.02 g tri-o-methylphenylphosphine, add 5 ml anhydrous toluene, 0.5 ml anhydrous N,N-dimethylformamide, The reaction was stirred for 48 hours under an argon atmosphere at 110°C. Cool the polymer to room temperature and slowly pour it into 70 ml of methanol. The precipitated polymer is filtered and washed with methanol and n-hexane successively in a Soxhlet extractor. Finally, it is dissolved in chloroform and precipitated into methanol, ...

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Abstract

The invention relates to an all-conjugate side-chain polymer and application thereof in polymer solar devices. By modifying the chemical structure of the polymer, the invention prepares a semiconductor polymer material with all-conjugate side-chain polymer. The semiconductor polymer material has the all-conjugate side-chain structure and lower HOMO energy level, and therefore, obtains excellent photoelectric properties, thereby being beneficial to developing low-cost high-performance polymer solar cell products. When the all-conjugate side-chain polymer and a fullerene derivative PCBM are prepared into a polymer solar device according to the mass ratio of 1:0.8-1:0.1, the maximum energy conversion efficiency of the solar cell can reach 6% or so under the conditions of low consumption of the fullerene derivative (1:0.5).

Description

technical field [0001] The invention relates to a polymer and its application, in particular to a polymer with fully conjugated side chains and its application in polymer solar devices, belonging to the technical field of organic polymer semiconductor materials. Background technique [0002] With the intensification of the world's energy crisis, it has become an urgent problem to find clean and cheap new energy to replace the widely exploited oil, coal, and natural gas. The inexhaustible solar energy has become the first new type of energy that people think of, and the solar cell that converts solar energy into electrical energy has become one of the high-tech countries that attach great importance to it. [0003] Since 1995 Alan J. Heeger et al. (G. Yu, J. Gao, J. C. Hummelen, F. Wudl, A. J. Heeger, science 1995, 270, 1789) reported for the first time that high-efficiency polymer solar cell devices with P3HT and PCBM as photosensitive layer materials were prepared by solu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/46
CPCY02E10/549
Inventor 袁建宇马万里陆佳灵徐忠杰
Owner SUZHOU UNIV
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