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N-type water/alcohol-soluble conjugated polyelectrolyte based on double-free-radical benzobithiadiazole as well as preparation and application of n-type water/alcohol-soluble conjugated polyelectrolyte

A technology of benzobisthiadiazole and conjugated polyelectrolyte, which is applied in the field of n-type water/alcohol-soluble conjugated polyelectrolyte, can solve the problem that it is difficult to effectively realize high-conductivity water/alcohol-soluble conjugated polymers, lack of benzene Problems such as quinone resonance transformation can meet the needs of environmentally friendly chemical processing, improve air stability, and improve transmission efficiency.

Pending Publication Date: 2021-04-13
CHINA PETROLEUM & CHEM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the lack of effective benzoquinone resonance transition in this type of structure, the electrons are mainly delocalized on the charge-absorbing unit, and it is difficult to effectively realize high conductivity water / alcohol-soluble conjugated polymers.

Method used

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  • N-type water/alcohol-soluble conjugated polyelectrolyte based on double-free-radical benzobithiadiazole as well as preparation and application of n-type water/alcohol-soluble conjugated polyelectrolyte
  • N-type water/alcohol-soluble conjugated polyelectrolyte based on double-free-radical benzobithiadiazole as well as preparation and application of n-type water/alcohol-soluble conjugated polyelectrolyte
  • N-type water/alcohol-soluble conjugated polyelectrolyte based on double-free-radical benzobithiadiazole as well as preparation and application of n-type water/alcohol-soluble conjugated polyelectrolyte

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] The chemical reaction equation for the preparation of BBT-Eh:

[0042]

[0043] Monomer 1 was synthesized according to the method reported in the literature (Benzodithiophene–Dithienylbenzothiadiazole Copolymers for Efficient Polymer Solar Cells: Side-Chain Effect on Photovoltaic Performance. ACS Applied Materials & Interfaces, 2018, 10(40), 34355-34362), and monomer 2 was 99% pure reagents were purchased commercially.

[0044] Take monomer 1 (2.45mmol) and monomer 2 (1.1mmol) into a reaction flask with a stirring bar, vacuumize for 5 minutes and pass nitrogen, add 50mL of toluene, and pump for 2 times; add under nitrogen Tetrakis(triphenylphosphine)palladium 36mg, stirred and heated to 100°C, reacted for 24 hours, after the reaction, toluene was removed by a rotary evaporator to obtain a crude product; The solvent was removed, and the crude product was purified by column chromatography to obtain the target compound BBT-EH as a green solid (70% yield). 1 H NMR (500...

Embodiment 2

[0046] The preparation of BBT-Eh-Br, the chemical reaction equation is as follows:

[0047]

[0048] Add BBT-EH (2mmol) dissolved in 25mL tetrahydrofuran in a 50mL round bottom flask with a magnetic stirrer, add N-bromosuccinimide (NBS, 4.05mmol) to the solution under nitrogen, The solution was stirred and reacted at room temperature in the dark for 4 hours, and the tetrahydrofuran was removed by a rotary evaporator, and then the crude product was dissolved in dichloromethane and eluted with a mixed solvent of petroleum ether and dichloromethane (1:1) reagent, the crude product was purified by column chromatography to afford the target compound BBT-EH-Br as a green solid (90% yield). 1 H NMR (500MHz, CDCl 3 ,ppm): 8.80-8.84(s,2H), 2.72-2.64(m,4H), 1.68-1.60(m,2H), 1.42-1.21(m,16H), 1.01-0.82(m,12H).

Embodiment 3

[0050] The preparation of IIG-C6Br, the chemical reaction equation is as follows:

[0051]

[0052] Under the protection of argon, the starting material (E)-6,6'-dibromo-[3,3'-diindolinylidene]-2,2'-dione (10mmol) was dissolved in 150mL ultra-dry N , N-dimethylformamide, add potassium carbonate (25mmol), heat to 85°C and stir for 1 hour, add 1,6-dibromohexane (60mmol), and heat up to 100°C for 24 hours, the reaction The solution was cooled to room temperature, and N,N-dimethylformamide was removed by a rotary evaporator to obtain a viscous crude product; using a mixed solvent of petroleum ether and dichloromethane (1:1) as the eluent, the The crude product was purified to afford the target compound IIG-C6Br as a red needle-like solid (15% yield). 1 H NMR (500MHz, CDCl 3 ,ppm): 9.09-9.05(d,2H),7.20-7.16(dd,2H),6.95-6.92(d,2H),3.80-3.71(t,4H),3.44-3.37(t,4H),1.91 -1.82 (p, 4H), 1.76-1.68 (p, 4H), 1.42-1.37 (m, 4H), 1.32-1.21 (m, 4H).

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Abstract

The invention belongs to the technical field of photoelectric materials, and discloses an n-type water / alcohol-soluble conjugated polyelectrolyte based on double-free-radical benzobithiadiazole as well as preparation and application of the n-type water / alcohol-soluble conjugated polyelectrolyte. The structure of the n-type water / alcohol-soluble conjugated polyelectrolyte based on the double-free-radical benzobithiadiazole is shown as a formula I, and A is a structure composed of one or more aromatic groups; RA or RB is a side chain with a water-alcohol soluble strong polar group, and at least one of RA and RB is a side chain with a water-alcohol soluble strong polar group; and n is a positive integer of 1-2000. The invention also discloses a preparation method of the conjugated polyelectrolyte. The conjugated polyelectrolyte is used for preparing organic photoelectric devices. The conjugated polyelectrolyte provided by the invention has excellent electron transport performance and air-stable n-type conductivity; the conjugated polyelectrolyte has high transmittance in a visible light region, and the light absorption of the active layer is not influenced; meanwhile, water / alcohol solubility is achieved, and solution processing can be achieved.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, in particular to n-type water based on diradical unit benzo[1,2-c:4,5-c']bis([1,2,5]thiadiazole) Alcohol-soluble conjugated polyelectrolyte and its preparation method and application. The conjugated polyelectrolyte is used as an electron transport layer in an organic optoelectronic device. Background technique [0002] The semiconductor materials used in optoelectronic materials and devices not only have the electronic characteristics of metals or semiconductors, but also have the characteristics of low cost, light weight, low temperature processing, and easy large-scale preparation, which meet the requirements of industrialized large-scale production and large-scale promotion. business prospects. Since the American Deng Qingyun research group [Organicelectroluminescent diodes.Applied Physics Letters, 1987,51,913.] proposed organic small molecule thin film electrolumines...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/42H01L51/46
CPCC08G61/126C08G61/123C08G2261/124C08G2261/143C08G2261/1412C08G2261/3142C08G2261/3223C08G2261/3246C08G2261/411C08G2261/312C08G2261/146C08G2261/72C08G2261/3241C08G2261/514C08G2261/91H10K85/151H10K30/00Y02E10/549
Inventor 黄飞唐浩然刘子贤张凯
Owner CHINA PETROLEUM & CHEM CORP
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