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Conjugated polymer material containing pyrrole indolodithiapentalene-dithieno benzothiadiazole and preparation method and application thereof

A technology of benzothiadiazole and conjugated polymers, which is applied in the field of photoelectric materials and can solve the problems of low photoelectric conversion efficiency

Inactive Publication Date: 2014-10-29
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Nevertheless, the photoelectric conversion efficiency of organic solar cell devices is much lower than that of inorganic solar cells

Method used

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  • Conjugated polymer material containing pyrrole indolodithiapentalene-dithieno benzothiadiazole and preparation method and application thereof
  • Conjugated polymer material containing pyrrole indolodithiapentalene-dithieno benzothiadiazole and preparation method and application thereof
  • Conjugated polymer material containing pyrrole indolodithiapentalene-dithieno benzothiadiazole and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] This example provides a conjugated polymer containing pyrrole indolodithiophene-dithienobenzothiadiazole, the chemical structure of which is shown in P1 (n=5):

[0062]

[0063] The preparation steps of the above P1 are as follows:

[0064] Step 1, preparation of compound A1

[0065] S10. Synthesis of compound E (2,2'-(2,5-dibromo-1,4-phenyl)bis(3-bromothiophene))

[0066] Compound C (2,5-dibromo-1,4-diiodobenzene) and compound D (3-bromo-2-trimethyltinthiophene) represented by the following structural formulas are provided:

[0067]

[0068] Under nitrogen protection, lithium chloride (2.54g, 60mmol), compound C (4.8g, 10mmol), Pd(PPh 3 ) 4 (287.5mg, 0.25mmol), cuprous chloride (5g, 50mmol), compound D (3.59g, 11mmol) and tetrahydrofuran (60mL), the reactant was stirred at room temperature for 1 hour, then heated to 50°C for 3 hours; Cool to room temperature, filter the solid generated by the reaction to obtain the crude product of Compound E, yield 40%, MS (...

Embodiment 2

[0098] This example provides a conjugated polymer containing pyrrole indolodithiophene-dithienobenzothiadiazole, the chemical structure of which is shown in P2 (n=60):

[0099]

[0100] The preparation steps of above-mentioned P2 are as follows:

[0101] Step 1, preparation of compound A2

[0102] S10. Synthesis of compound E (2,2'-(2,5-dibromo-1,4-phenyl)bis(3-bromothiophene))

[0103] Provide compound C (2,5-dibromo-1,4-diiodobenzene) and compound D (3-bromo-2-trimethyltinthiophene), see Example 1 for the structural formula;

[0104] Under nitrogen protection, lithium chloride (2.63g, 62mmol), compound C (4.8g, 10mmol), Pd(PPh 3 ) 2 Cl 2 (0.7mg, 0.001mmol), cuprous chloride (5.15g, 52mmol), compound D (4.89g, 15mmol) and DMF (60mL), after the reaction was stirred at room temperature for 2 hours, it was heated to 55 ° C for 4 hours ; Cool to room temperature, filter the solid generated by the reaction to obtain the crude product of Compound E, with a yield of 39%, MS ...

Embodiment 3

[0128] This example provides a conjugated polymer containing pyrrole indolodithiophene-dithienobenzothiadiazole, the chemical structure of which is shown in P3 (n=30):

[0129]

[0130] The preparation steps of above-mentioned P3 are as follows:

[0131] Step 1, preparation of compound A3

[0132] S10. Synthesis of compound E (2,2'-(2,5-dibromo-1,4-phenyl)bis(3-bromothiophene))

[0133] Provide compound C (2,5-dibromo-1,4-diiodobenzene) and compound D (3-bromo-2-trimethyltinthiophene), see Example 1 for the structural formula;

[0134] Under the protection of nitrogen, lithium chloride (2.59g, 61mmol), compound C (4.8g, 10mmol), Pd(PPh 3 ) 4 (578mg, 0.5mmol), cuprous chloride (5.05g, 51mmol), compound D (3.91g, 12mmol) and toluene (60mL), the reactants were stirred at room temperature for 1.5 hours, then heated to 52°C for 3.5 hours; Cool to room temperature, filter the solid generated by the reaction to obtain the crude product of Compound E, the yield is 42%, MS (EI) ...

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Abstract

The invention belongs to the field of conjugated polymer materials, and in particular relates to a conjugated polymer material containing pyrrole indolodithiapentalene-dithieno benzothiadiazole. The material has a structural formula shown as P, wherein R1 represents C1-C16 alkyl, R2 and R3 represent H or C1-C16 alkyl, and n is an integer between 5-60. The conjugated polymer material containing pyrrole indolodithiapentalene-dithieno benzothiadiazole has excellent carrier mobility, lower energy gap and wider luminous absorption range, and excellent solubility and processability. The invention also provides the preparation method and application of the conjugated polymer material containing pyrrole indolodithiapentalene-dithieno benzothiadiazole to solar cell device, organic electroluminescent device or organic field effect transistor device.

Description

technical field [0001] The invention relates to the field of photoelectric materials, in particular to a conjugated polymer material containing pyrrole indolodithiophene-dithienobenzothiadiazole and its preparation method and application. Background technique [0002] Organic solar cell devices have some advantages that inorganic solar cells cannot match, such as low cost, simple manufacturing process, light product weight, and large-area flexible preparation. Therefore, as a potential renewable energy source, it has attracted widespread attention. The performance of organic solar cell devices has steadily improved over the past decade, with energy conversion efficiencies approaching 10%. Nevertheless, the photoelectric conversion efficiency of organic solar cell devices is much lower than that of inorganic solar cells. Therefore, in order to realize the commercialization of organic solar cell devices, the development of new organic semiconductor materials is of great signi...

Claims

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Application Information

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IPC IPC(8): C08G61/12C07D519/00H01L51/46H01L51/54H01L51/30
CPCY02E10/549
Inventor 周明杰管榕李满园
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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