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Polymer material containing Ladder type aromatic fused heterocycles

A technology of condensed heterocyclic and polymer films, applied in the field of organic thin film battery materials

Inactive Publication Date: 2012-07-04
FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But its open circuit voltage is only 0.82V

Method used

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  • Polymer material containing Ladder type aromatic fused heterocycles
  • Polymer material containing Ladder type aromatic fused heterocycles
  • Polymer material containing Ladder type aromatic fused heterocycles

Examples

Experimental program
Comparison scheme
Effect test

example 1、2

[0029] Example 1, 2,7-dibromo-N-2-ethylhexylcarbazole

[0030] Add 4.0 g of 2,7-dibromocarbazole and 3.6 g of K to dry 40 mL of DMF 2 CO 3 . DMF was heated to 80°C and nitrogen sparged for 2 hours, then 4.6 g of 2-ethylhexyl bromide was added. After the mixture was reacted at 80° C. for 24 hours, it was cooled to room temperature, and then 100 ml of water was added. It was extracted three times with dichloromethane, and the organic phase was washed with water and brine, and finally dried with magnesium sulfate. After the solvent was distilled off under reduced pressure, 100 ml of methanol was added, and a white solid was precipitated after cooling in the refrigerator. After suction filtration under reduced pressure and drying, 4.3 g of white solid was obtained, with a yield of 80%. 1 H NMR (400MHz, CDCl 3 , δ): 7.88(d, 2H, J=8.0Hz), 7.50(s, 2H), 7.33(d, 2H, J=8.0Hz), 4.08-4.05(m, 2H), 2.01-1.99(m, 1H), 1.37-1.28 (m, 8H), 0.93-0.87 (m, 6H).

example 2、3

[0031] Example 2, 3,6-diheptanyl-2,7-dibromo-N-2-ethylhexylcarbazole

[0032] Add 2.3 g of 2,7-dibromo-N-2-ethylhexylcarbazole and 2.79 g of AlCl to 30 ml of dichloromethane 3 , slowly added 1.65 g of heptanoyl chloride under ice-cooling. After heating the reaction solution to reflux for 5 hours, cool it, add ice and dichloromethane, dissolve the insoluble precipitate with 2M hydrochloric acid, wash the organic phase with water, wash with brine, and dry over magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was subjected to silica gel column chromatography with a mixed solvent of 20% ethyl acetate and 80% petroleum ether to obtain 2.96 g of yellow oil. 85% yield. 1 H NMR (400MHz, CDCl 3 , δ): 8.16 (d, 2H, J=1.2Hz), 7.59 (d, 2H, J=1.2Hz), 4.10-4.07 (2H, m), 3.07-3.03 (m, 4H), 2.00-1.90 ( m, 1H), 1.81-1.73(m, 4H), 1.45-1.24(m, 20H), 0.96-0.81(m, 12H). 13 CNMR (100MHz, CDCl 3 , δ): 203.57, 142.78, 133.16, 121.34, 121.12, 117.35, 114.76,...

example 3、3

[0033] Example 3, 3,6-diheptanyl-2,7-dithiophene-N-alkylcarbazole

[0034]Add 2.9 g of 3,6-diheptanonyl-2,7-dibromo-N-2-ethylhexylcarbazole and 6.5 g of 2-tributylstannylthiophene to dry DMF and bubble nitrogen for 1 h After adding 150 mg Pd (PPh 3 ) 4 . Heat the mixture to 90°C and maintain this temperature for 12 hours. After cooling, add water, extract 3 times with petroleum ether, and wash the obtained organic phase with water and brine, MgSO 4 dry. After the solvent was distilled off under reduced pressure, the residue was subjected to silica gel column chromatography with a mixed solvent of 20% ethyl acetate and 80% petroleum ether to obtain 2.2 g of a yellow oil with a yield of 75%. 1 H NMR (400MHz, CDCl 3 , δ): 8.23 ​​(s, 2H), 7.43-7.41 (m, 4H), 7.12-7.10 (m, 2H), 7.06 (dd, J 1 = 3.6Hz,J 2 =1.2Hz, 2H), 4.20(m, 2H), 2.48(t, J=7.6Hz, 4H), 2.09(m, 1H), 1.61-1.51(m, 4H), 1.44-1.24(m, 20H) , 0.95-0.81(m, 12H) 13 C NMR (100MHz, CDCl 3 ,δ):207.47,142.91,142.53,134....

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Abstract

The invention provides a method for preparing a polymer material containing Ladder type aromatic fused heterocycles. The material can be widely applied to an organic thin film field effect transistor and an organic thin film solar cell. The material takes the Ladder type aromatic fused heterocycles as a basic framework and the forbidden frequency width of the material is reduced by introducing heteroatoms; and meanwhile, the Ladder type framework is good for keeping a higher highest occupied molecular orbital (HOMO), so as to realize greater open voltage.

Description

technical field [0001] The invention relates to an organic film battery material, especially a polymer material containing a Ladder type aromatic condensed heterocyclic ring and its derivatives. Background technique [0002] Organic thin-film (heterojunction) solar cells use n-type and p-type materials of organic semiconductors. Under sunlight irradiation, a potential difference is generated in the p-n junction band gap. This organic thin-film cell can be spin-coated, rolled Low-cost manufacturing techniques such as roll-to-roll and inkjet printing can also be applied to the surface of plastic films or other materials to realize flexible solar cells. Although the conversion efficiency of organic thin film solar cells is still lower than that of inorganic solar cells, it has shown great potential, especially in the last 3-4 years with the design and synthesis of new organic thin film solar cell materials, the development of organic thin film solar cells The conversion effici...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/46H01L51/30
CPCY02E10/549
Inventor 郑庆东陈善慈汤昌泉
Owner FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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