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Conjugated polymer, and preparation method and application thereof

A technology of polymers and groups, applied in semiconductor/solid-state device manufacturing, photovoltaic power generation, electrical components, etc., can solve problems such as reduced energy conversion efficiency, no increase in device open circuit voltage, and limited application range

Active Publication Date: 2013-12-11
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this method has its limitations. For some high-efficiency D-A polymers, fluorine substituents cannot be introduced on the acceptor unit, thus limiting the scope of application of this method; at the same time, LU et al. tried to introduce The results show that although the HOMO energy level of the polymer is effectively reduced, the open circuit voltage of the device is not improved, and the energy conversion efficiency is significantly reduced.

Method used

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  • Conjugated polymer, and preparation method and application thereof
  • Conjugated polymer, and preparation method and application thereof
  • Conjugated polymer, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] Example 1, 2,6-bis(trimethyltinyl)-4,8-bis(5-(2-ethylhexyl)-4-fluorothiophen-2-yl)-benzo[1,2-b : Synthesis of 4,5-b']dithiophene

[0066] chemical reaction flow chart Figure 7 Shown, concrete reaction steps and reaction conditions are as follows:

[0067]Compound 1: Under argon protection, lithium diisopropylamide (2.0M, 12mL) was slowly injected into 3-bromo-2-(2-ethylhexyl)thiophene (6.6g, 24mmol) at -78°C ) in tetrahydrofuran (30mL), react at low temperature for 1 hour, then slowly rise to room temperature; then add 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8 - Diketone (1.76g, 8.0mmol), heated to 50°C for 2 hours, cooled to room temperature, then added a mixture of stannous chloride dihydrate (12.6g, 56mmol) and dilute hydrochloric acid (10%, 25mL) , react overnight at 50°C. Then the mixture was poured into ice water, extracted several times with diethyl ether, the organic phases were combined, dried with magnesium sulfate, and the dark yellow liquid was obta...

Embodiment 2

[0077] Example 2. Poly{[4,8-bis(5-(2-ethylhexyl)-4-fluorothiophen-2yl)-benzo[1,2-b:4,5-b']dithiophene -2,6-diyl]-co-[2-hexyldecyl-4,6-bis(thiophen-2-yl)-3-fluoro-thiophene[3,4-b]thiophene-2-ester-5 ,5'-diyl]} (polymer PBT-3F) synthesis.

[0078] chemical reaction flow chart Figure 8 Shown, concrete reaction steps and reaction conditions are as follows:

[0079] Take the monomer 2,6-bis(trimethyltinyl)-4,8-bis(5-(2-ethylhexyl)-4-fluorothiophen-2-yl)-benzo[1,2-b: 4,5-b']dithiophene (compound 5, 0.235 g, 0.25 mmol) and the monomer 2-hexyldecyl-4,6-bis(5-bromothiophen-2-yl)-3-fluoro-thiophene [ 3,4-b] thiophene-2-ester (0.187g, 0.25mmol), dissolved in toluene (10mL), exhausted with argon for 20 minutes, then added the catalyst tetrakis (triphenylphosphine) palladium (0 ) (20mg) and continue to expel the air for 30 minutes. Polymerization was then stopped at reflux temperature of toluene for 12 hours. The polymer solution was cooled to room temperature, slowly poured into me...

Embodiment 3

[0080] Example 3. Processability of the polymers of the invention and measurement of the optical bandgap using absorption spectroscopy

[0081] The polymer prepared in Example 2 was mixed with various organic solvents, including chlorinated solvents such as chloroform, dichloromethane, chlorobenzene and dichlorobenzene, and other solvents such as methanol, toluene and tetrahydrofuran. The polymer PBT-3F was found to have good solubility in chlorinated solvents, but insoluble in methanol. High-quality films were prepared by spin-coating polymer PBT-3F in dichlorobenzene onto glass slides.

[0082] The absorption spectrum that the polymkeric substance that embodiment 2 prepares records under chloroform solution and film state is shown in image 3 . The optical bandgap of polymers uses the empirical formula (Eg=1240 / λ 吸收起始 , where: E g is the optical bandgap of the polymer; λ 吸收起始 is the starting point of the absorption spectrum in the long-wave direction) and is calculated ...

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Abstract

The invention discloses a conjugated polymer, and a preparation method and an application thereof. The structure of the conjugated polymer is represented by formula I shown in the specification. The invention also discloses a photovoltaic device (comprising a solar battery device). The photovoltaic usually comprises a P-type collection layer, an electron collection and a photovoltaic material layer between the P-type collection layer and the electron collection layer; and the photovoltaic material layer at least comprises the polymer or a semiconductor composition. A method introducing a fluoro substituent to the conjugate side chain of a D-A conjugated polymer donor unit, provided by the invention, effectively adjusts the molecular energy level of the polymer without influencing the optical band gap, so the photoelectric conversion efficiency of the device is improved.

Description

technical field [0001] The invention relates to a conjugated polymer and its preparation method and application. Background technique [0002] In recent years, polymer solar cells (PSCs), as a new type of organic thin-film solar cells, are sandwiched between ITO transparent and conductive films (active layers) of conjugated polymer donors and fullerene acceptors. The composition between the glass positive electrode and the low work function metal negative electrode has attracted widespread attention due to its outstanding advantages such as simple preparation process, low cost, light weight, and flexible devices. The highest energy of the laboratory small-area device reported in the literature The conversion efficiency (PCE) has been increased to 7-8% (Xia Guo, Maojie Zhang, Jiahui Tan, Shaoqing Zhang, Lijun Huo, Wenping Hu, Yongfang Li, and Jianhui Hou, Adv.Mater.2012.24, 6536–654; Lijun Huo , Shaoqing Zhang, Xia Guo, Feng Xu, Yongfang Li, and Jianhui Hou, Angew. Chem. Int...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/46
CPCY02E10/549
Inventor 张茂杰国霞侯剑辉
Owner INST OF CHEM CHINESE ACAD OF SCI
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