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Terpolymer containing triazol isoindol-5,7(2H,6H)-dione unit and preparation method and application thereof

A technology of terpolymer and isoindole, which is applied in chemical instruments and methods, electrical components, semiconductor/solid-state device manufacturing, etc., can solve the problems of low efficiency of organic solar cells, achieve wide absorption, improve solubility, wide The effect of the optical bandgap

Inactive Publication Date: 2017-07-25
SOUTH CHINA UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, the current efficiency of organic solar cells is too low. In order to achieve high-efficiency photoelectric conversion, from the perspective of active layer materials, it is necessary to combine the advantages of each material to obtain better active layer materials, thereby obtaining high conversion. efficiency

Method used

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  • Terpolymer containing triazol isoindol-5,7(2H,6H)-dione unit and preparation method and application thereof
  • Terpolymer containing triazol isoindol-5,7(2H,6H)-dione unit and preparation method and application thereof
  • Terpolymer containing triazol isoindol-5,7(2H,6H)-dione unit and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] 2,6-Dioctyl-4,8-bis(4-(2-octyldodecyl)thiophen-2-yl)-[1,2,3]triazolo[4,5-f] Preparation of isoindole-5,7)-dione (12):

[0038] (1) In a 500mL three-neck flask, under nitrogen protection, add compound 1 (13.83g, 41.66mmol), compound 2 (34.2g, 91.65mmol), and then add 300mL tetrahydrofuran as a solvent, heat to 120°C, and react for 12h. Treatment: Put the reaction mixture into a single-necked bottle and mix it with silica gel powder for rotary evaporation, then pass through a silica gel column for column purification to obtain a yellow oily liquid. Finally, 11.21 g of yellow oily liquid was obtained. Yield: 83.23%. 1 H NMR (500MHz, CDCl 3 )δ7.33(d, J=1.4Hz, 2H), 7.15(d, J=1.3Hz, 2H), 2.56(d, J=6.8Hz, 4H), 1.61(d, J=5.9Hz, 2H) , 1.31–1.23(m,64H), 0.88(t,J=7.0Hz,12H). 13 C(151MHz, CDCl3) 143.73, 136.68, 133.99, 132.80, 38.90, 33.26, 31.93, 31.92, 29.98, 29.67, 29.66, 29.63, 29.37, 29.34, 26.60, 22.70, 14.13. The chemical reaction equation is as follows:

[0039]

[...

Embodiment 2

[0059] 4,6-bis(5-bromo-4-(2-octyldodecyl)thiophen-2-yl)-2,6-dioctyl-[1,2,3]triazolo[4, Preparation of 5-f]isoindole-5,7(2H,6H)-dione:

[0060]

[0061] Add compound 12 (1.08g, 1.88mmol) into the reaction flask, add 80ml of chloroform to dissolve, then add 3ml of AcOH, weigh NBS (0.77g, 4.3mmol) into the reaction flask, pass in nitrogen, and cover the reaction device with a black bag Cover it, raise the temperature to 120°C, react for 12 hours, and end the reaction. Post-treatment: extract with DCM, while mixing silica gel powder, purify the crude product with silica gel column, the volume ratio of petroleum ether: dichloromethane is 2:1 (v / v), and finally recrystallize with methanol and tetrahydrofuran. Finally, yellow oily liquid 4,6-bis(5-bromo-4-(2-octyldodecyl)thiophen-2-yl)-2,6-dioctyl-[1,2,3]tri Azolo[4,5-f]isoindole-5,7(2H,6H)-dione, 1.2 g, yield: 88%. 1H NMR (500MHz, CDCl3) δ7.92(s, 2H), 4.76(t, J=7.2Hz, 2H), 3.83–3.52(m, 2H), 2.61(d, J=7.0Hz, 4H), 2.26 –2.06(m,...

Embodiment 3

[0063] Preparation of copolymer PTZBI-2TOD-T-0%BDT:

[0064]

[0065] Under argon protection, in a 10mL microwave tube, add 4,8-bis(5-bromooxin-2-yl)-6-octyl-5H-[1,2,5]selenadiazolo[3,4 -f] isoindole-5,7(6H)-dione (129.56mg, 0.10mmol), 2,6-dibromo-4,8-bis(5-(2-ethylhexyl)thiophene-2 -yl)benzo[1,2-b:4,5-b']dithiophene (73.6mg, 0.1mmol), tetrakis(triphenylphosphine)palladium (8mg) and xylene (2mL), microwave at 200°C Reacted for 45min, after cooling down to room temperature, the reaction solution was precipitated in methanol, carried out Soxhlet extraction with methanol, acetone, and n-hexane successively, and then added an aqueous solution of sodium diethyldithiocarbamate trihydrate (225mg, 1mmol, 100 mL of water) was stirred at 60° C. for 8 hours, the palladium catalyst in the reaction was removed, Soxhlet extraction was performed with methanol, acetone, and n-hexane, and dried to obtain a dark green solid (123 mg), yield: 82%. Proton NMR spectrum: (CDCl 3 )δ(ppm): 1 H ...

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Abstract

The invention discloses a terpolymer containing a triazol isoindol-5,7(2H,6H)-dione unit and a preparation method and application thereof. The preparation method comprises the following step of enabling a monomer of an electron donor unit and a monomer containing the triazol isoindol-5,7(2H,6H)- dione unit to generate still coupling copolymerizing reaction, so as to obtain the ternary copolymer containing the triazol isoindoline-5,7(2H,6H)-diketone unit. The ternary copolymer containing the triazol isoindol-5,7(2H,6H)-dione unit has the advantages that the fluorescence property is realized; the absorbing range of sunlight is wider; the terpolymer can be well applied to the fields of preparation of light emitting layers of polymer light emitting diodes, polymer field effect transistors and activating layers of polymer solar batteries.

Description

technical field [0001] The invention relates to the field of optoelectronic materials, in particular to a terpolymer containing triazoloisoindole-5,7(2H,6H)-dione units, a preparation method and application thereof. Background technique [0002] Solar energy is a green and renewable resource. There are many types of active layer materials for organic solar cells and the chemical structure of organic molecules is easy to modify. The preparation and purification of compounds is simple and easy. It can be made into large-area flexible thin-film devices and has future cost advantages. and wide distribution of resources. Organic solar cells can be prepared as films, and can be fabricated to form flexible solar cells on rollable and foldable substrates. Organic solar cells have the advantages of large manufacturing area, low cost, simplicity, and flexibility. Therefore, it has great commercial development and application prospects. [0003] However, the current efficiency of or...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C09K11/06H01L51/00H01L51/46H10K99/00
CPCC09K11/06C08G61/123C08G61/124C08G61/126C08G2261/228C08G2261/3241C08G2261/3243C08G2261/3223C08G2261/145C08G2261/1412C08G2261/124C08G2261/91C08G2261/344C08G2261/522C08G2261/414C08G2261/354C08G2261/92C08G2261/95C09K2211/1458C09K2211/1466H10K85/151Y02E10/549
Inventor 应磊马小娟黄飞曹镛
Owner SOUTH CHINA UNIV OF TECH
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