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Conjugated polymer containing 1,2,3 triazoloisoindole-5,7(2h,6h)-dione and its preparation method and application

A conjugated polymer, isoindole technology, applied in the field of polymers, can solve problems such as insufficient species development, and achieve the effects of good solution processability, excellent optoelectronic properties, and improved solubility

Active Publication Date: 2019-04-09
SOUTH CHINA UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the development of organic solar conjugated molecular materials is insufficient at present. In order to achieve high-efficiency photoelectric conversion, from the perspective of active layer materials, each active layer material needs to have high-efficiency absorption of sunlight and high carrier mobility. , resulting in a high conversion efficiency

Method used

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  • Conjugated polymer containing 1,2,3 triazoloisoindole-5,7(2h,6h)-dione and its preparation method and application
  • Conjugated polymer containing 1,2,3 triazoloisoindole-5,7(2h,6h)-dione and its preparation method and application
  • Conjugated polymer containing 1,2,3 triazoloisoindole-5,7(2h,6h)-dione and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] 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):

[0039]

[0040] In a 500mL three-neck flask, under nitrogen protection, add compound 1 (13.83g, 41.66mmol), compound 2 (34.2g, 91.65mmol), then add 300mL tetrahydrofuran as a solvent, heat to 120 ° C, and determine the reaction process by spotting the plate Post-processing: Put the reaction mixture into a one-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 a yellow oily liquid is 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)

[0041] δ143.73, 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.

[0...

Embodiment 2

[0061] 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:

[0062]

[0063] 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, and blow nitrogen. Cover the reaction apparatus with a black bag. Spot the plate to detect the progress of the reaction and end the reaction. Post-treatment: extract with DCM, and mix silica gel powder at the same time, purify the crude product with silica gel column, the volume ratio of petroleum ether:dichloromethane is 2:1. Finally, recrystallization was carried out with methanol and tetrahydrofuran. Finally, 4,6-bis(5-bromo-4-(2-octyldodecyl)thiophen-2-yl)-2,6-dioctyl-[1,2,3]triazolo[ 4,5-f]isoindole-5,7(2H,6H)-dione yellow oily liquid 1.2g, yield: 88%. 1 H 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)...

Embodiment 3

[0065] Poly(5"-methyl-3-(2-octyldodecyl)-[2,2':5',2"-trithiophene]-5-yl)-8-(5-methyl- 4-octyldodecyl)thiophen-2-yl)-2,6-dioctyl-[1,2,3]triazolo[4,5-f]isoindole-5,7(2H , the preparation of 6H)-diketone, synthetic route and synthetic method are as follows:

[0066]

[0067] Under argon protection, in a 10mL microwave tube, add 4,8-bis(5-bromothien-2-yl)-6-octyl-5H-[1,2,5]selenadiazolo[3,4- f] Isoindole-5,7(6H)-dione (129mg, 0.10mmol), DT (49.2mg, 0.10mmol), tetrakis(triphenylphosphine)palladium (8mg) and xylene (2mL), Microwave at 200°C for 45 minutes, after the reaction has cooled to room temperature, precipitate the reaction solution in methanol, perform Soxhlet extraction with methanol, acetone, and n-hexane successively, and then add the aqueous solution of sodium diethyldithiocarbamate trihydrate (225mg, 1mmol, 100mL water) was stirred at 60°C for 8 hours, the palladium catalyst in the reaction was removed, Soxhlet extraction was carried out with methanol, acetone, n-h...

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Abstract

The invention discloses a conjugated polymer containing 1,2,3 triazoloisoindole-5,7(2H,6H)-dione and its preparation method and application, belonging to the application of polymers in optoelectronic materials and device field. The preparation method comprises the following steps: the electron donor unit D and 2,6‑R, R 1 ‑[1,2,3]triazolo[4,5‑f]isoindole‑4,8‑Ar 1 、Ar 2 ‑5,7(2H, 6H)‑diketone monomer undergoes still coupling copolymerization reaction to obtain conjugate polymerization containing 1,2,3 triazoloisoindole‑5,7(2H, 6H)‑diketone things. The conjugated polymer prepared by the invention has fluorescence and broad absorption of sunlight, so it can be used to make polymer light-emitting diode devices, polymer field effect transistors and active layers of polymer solar cells.

Description

technical field [0001] The invention relates to the field of polymers applied to optoelectronic materials and devices, in particular to a conjugated polymer containing 1,2,3 triazoloisoindole-5,7(2H,6H)-dione and its preparation method with application. 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. However...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/42H01L51/05
CPCC08G61/123C08G61/124C08G61/126C08G2261/124C08G2261/52C08G2261/91C08G2261/92C08G2261/95C08G2261/1412C08G2261/18C08G2261/3223C08G2261/3241C08G2261/3243C08G2261/414H10K10/46H10K10/20H10K30/00Y02E10/549
Inventor 黄飞马小娟应磊曹镛
Owner SOUTH CHINA UNIV OF TECH
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