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Polymer of phenazine structure and preparation method and application thereof

A polymer, phenazine technology, used in semiconductor/solid-state device manufacturing, photovoltaic power generation, electrical components, etc., to achieve the effect of increasing the degree of conjugation

Active Publication Date: 2016-08-31
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the contrary, BDT is combined with quinoxaline as the main skeleton of the polymer's electricity-deficient unit to form a polymer containing a thiophene-substituted phenazine structure (that is, C1-C4 is substituted by thiophene), and its preparation method and application have not yet been reported.

Method used

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  • Polymer of phenazine structure and preparation method and application thereof
  • Polymer of phenazine structure and preparation method and application thereof
  • Polymer of phenazine structure and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Preparation of 2-fluoro-1,4-alkoxyphenazine[6,7;8,9]bis(5-bromothiophene)

[0030] 4-Fluoro-3,6-dioctyloxy-phenylenediamine (0.4g, 1mmol) and 4,5-diketone-2,7-dibromo-dithienoacene (0.22g, 1mmol) were dissolved in In acetic acid (40mL), the temperature was raised to 60°C, and the reaction was incubated for 3h. Suction filtration and washing the filter cake with ethanol gave 2-fluoro-1,4-octyloxyphenazine[6,7;8,9]dithiophene (414 mg, 73%). The obtained product was dissolved in THF / DMF (5 / 10mL), and NBS (265mg, 1.5mmol) was added at 40°C. After reacting for 5h, the organic phase was washed with water and extracted with dichloromethane, dried over anhydrous magnesium sulfate to obtain 2-fluoro - 1,4-octyloxyphenazin[6,7;8,9]bis(5-bromothiophene) (360 mg, 68%).

[0031] The NMR characterization data are: 1 H NMR (CDCl 3 ,500MHz,ppm), δ=7.23(s,2H),6.79(d,1H),3.77-4.02(m,4H),1.96(m,2H),1.29-1.33(m,16H),0.94(t ,12H).

[0032]

Embodiment 2

[0034] Preparation of Polymers Shown in Formula II

[0035]

[0036] The reaction was carried out under nitrogen protection, 2-fluoro-1,4-octyloxyphenazin[6,7;8,9]bis(5-bromothiophene) (222mg, 0.3mmol) and 2,5-bis( Trimethyltin)thiophene (198.6mg, 0.3mmol) was dissolved in 10mL of toluene, nitrogen gas was passed for 0.5h, and the catalyst tris(dibenzylideneacetone)dipalladium (5.5mg, 0.006mmol) and the ligand tri-o-toluene were added Base phosphorus (9.8mg, 0.0024mmol), continue to ventilate for 0.5h, then start heating, reflux at 100°C for 24h, cool the system naturally at room temperature, add dropwise to methanol to settle, filter, collect the filter residue and bake in a vacuum oven at 50°C for 12h , the obtained polymer was sequentially extracted with methanol, n-hexane, and chloroform by Soxhlet, the chloroform extract was concentrated, dropped into methanol for sedimentation, and filtered to obtain 139 mg of polymer II with a yield of 72%, a number average molecular...

Embodiment 3

[0042] The preparation of polymkeric substance shown in formula Ⅲ

[0043]

[0044] Same as Example 2, the electron-deficient unit is 2,3-difluoro-1,4-octyloxyphenazine[6,7;8,9]bis(5-bromothiophene), obtained by the same polymerization method Polymer Ⅲ, yield 66%, number average molecular weight 36.67kDa, distribution coefficient 2.75.

[0045] Absorption spectrum test: Polymer III was completely dissolved in chloroform and spin-coated with a homogenizer to form a film, and the solution and film were tested by UnicoUV-2102 ultraviolet-visible absorption spectrometer respectively. The optical energy gap (E g ) is 1.67eV.

[0046] Electrochemical test: use CHI660D electrochemical workstation, use glassy carbon electrode as working electrode, platinum wire electrode as counter electrode, Ag / Ag + The electrode is the reference electrode, Bu 4 N·PF 6 As an electrolyte, in acetonitrile solvent, the HOMO energy of the polymer Ⅲ thin film was determined by cyclic voltammetry to...

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Abstract

The invention provides a polymer of a phenazine structure and a preparation method and application thereof. The structural formula of the polymer is shown in the formula I. Dithienyl acene is used as a main framework of an electron deficiency unit to be introduced into an azophenylene molecular structure; the conjugation degree of the molecules is effectively increased due to the fact that the prepared polymer is of the five-membered ring structure with the high planarity. The polymer has the wide absorption spectrum (the optical energy gap is smaller than 1.65eV), low HOMO energy level (lower than -5.5eV) and high migration rate (10<-4>-10<-3>cm<2> / Vs) and is applied to a photovoltaic device, and therefore the photoelectric conversion efficiency larger than 6% can be obtained.

Description

technical field [0001] The invention belongs to the technical field of photoelectric functional materials, and in particular relates to a polymer containing a phenazine structure and a preparation method and application thereof. Background technique [0002] With the continuous development of the global economy, the energy crisis and environmental problems are becoming increasingly severe, and the development and utilization of new energy sources is imminent. Solar energy, as an abundant green energy source, is regarded as the main force of future energy sources. As a new type of photovoltaic device, polymer solar cells have received extensive attention in recent years in their development and application, and have become a global research hotspot. [0003] The photoelectric conversion efficiency of photovoltaic devices is the standard to measure the quality of the battery, which is mainly affected by the open circuit voltage, short circuit current and fill factor. Theoreti...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/46
CPCC08G61/122C08G61/126C08G2261/3241C08G2261/3243C08G2261/1424C08G2261/18C08G2261/146C08G2261/91C08G2261/512H10K85/113Y02E10/549
Inventor 韦玮刘硕
Owner NANJING UNIV OF POSTS & TELECOMM
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