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Chlorine replaced polythiophene derivative and solar battery

A polythiophene derivative, solar cell technology, applied in circuits, photovoltaic power generation, electrical components, etc., can solve the problems of low open circuit voltage, limit energy conversion efficiency, etc., and achieve the effect of high open circuit voltage

Active Publication Date: 2019-09-17
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the strong electron-rich properties of the thiophene unit, P3HT has a higher highest occupied molecular orbital (HOMO) energy level (ˉ-4.90eV), resulting in a lower open-circuit voltage for P3HT-based solar cells, which limits its energy efficiency. Further improvement in conversion efficiency

Method used

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  • Chlorine replaced polythiophene derivative and solar battery
  • Chlorine replaced polythiophene derivative and solar battery
  • Chlorine replaced polythiophene derivative and solar battery

Examples

Experimental program
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preparation example Construction

[0025] Preparation of raw materials M1 and M1',:

[0026]

[0027] (M1) and (M1'); wherein R is a branched alkyl chain in the formula (M1), and R is an alkyl chain in the formula (M1').

[0028] Preparation of raw materials N1(II-1)(II-4), N2(II-2)(II-5), N3(II-3)(II-6):

[0029]

[0030] Preparation of product:

[0031]

[0032]

[0033]

Embodiment 1

[0034] Embodiment 1: (2-butyloctyl)-2-bromothiophene-3-carboxylate

[0035]

[0036] 2-Bromo-3-carboxythiophene (1.50g, 7.28mmol), DCC (0.87g, 8.74mmol), DMAP (0.23g, 2.55mmol), 2-butyl-1-octanol (2.70g, 14.50mmol ) was dissolved in 50 mL of dichloromethane and stirred at room temperature for 24 hours. Then it was poured into water, filtered, and the filter cake was washed several times with dichloromethane. The filtrate was collected, washed three times with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent was spin-dried, and the crude product was subjected to silica gel column chromatography (the eluent was petroleum ether (PE): CH 2 Cl 2 =6:1) Purified to obtain colorless liquid (2-butyloctyl)-2-bromothiophene-3-carboxylate. The structural characterization data are as follows: 1 H NMR (CDCl 3 ,400MHz): δ(ppm)=7.92(d,J=1.6Hz,1H),7.52(d,J=1.6Hz,1H),4.14(d,J=5.6Hz,2H),1.75-1.66(m ,1H),1.45-1.19(m,16H),0.85-0.90(m,6H).

Embodiment 2

[0037] Example 2: (2-hexyldecyl)-2-bromothiophene-3-carboxylate

[0038]

[0039] 2-Bromo-3-carboxythiophene (1.50g, 7.28mmol), DCC (0.87g, 8.74mmol), DMAP (0.23g, 2.55mmol), 2-hexyl-1-decanol (3.50g, 14.50mmol) Dissolve in 50 mL of dichloromethane and stir at room temperature for 24 hours. Then it was poured into water, filtered, and the filter cake was washed several times with dichloromethane. The filtrate was collected, washed three times with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent was spin-dried, and the crude product was subjected to silica gel column chromatography (the eluent was petroleum ether (PE): CH 2 Cl 2 =6:1) Purified to obtain colorless liquid (2-hexyldecyl)-2-bromothiophene-3-carboxylate. The structural characterization data are as follows: 1 H NMR (CDCl 3 ,400MHz): δ(ppm)=7.94(d,J=1.6Hz,1H),7.54(d,J=1.6Hz,1H),4.17(d,J=5.6Hz,2H),1.78-1.68(m ,1H),1.46-1.19(m,24H),0.85-0.90(m,6H).

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Abstract

The invention belongs to the technical field of organic photoelectricity, and particularly relates to a chlorine replaced polythiophene derivative and a solar battery. The chlorine replaced polythiophene derivative is characterized by being shown as a formula (I) shown in the accompanying drawing, wherein X and X' are H, F or Cl; R is C8-C24; n is a repeated unit. An electron withdrawing group is introduced into a thiophene compound; the HOMO energy grade of a polymer can be pulled down. The helium atom has high electricity negative performance. The helium atom is introduced into the conjugated polymer, so that the lower HOMO energy grade can be realized. More importantly, the chlorine replaced polymer can be more easily synthesized and can be obtained by using commercial raw materials by a simple synthesis method.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectricity, and in particular relates to a chlorine-substituted polythiophene derivative and a solar cell. Background technique [0002] Organic solar cells have the advantages of low cost, light weight, flexible devices and large-area devices, so they have attracted extensive attention (Science 1995, 270, 1789-1791; Acc.Chem.Res. 2009, 42, 1709-1718; Chem . Rev. 2015, 115, 12666-12731; Nat. Photon. 2015, 9, 174-179; Nat. Photon. 2012, 6, 153-161; J. Am. Chem. Soc. 2015, 137, 14149-14157). In recent years, with the development of A-D-A small molecule acceptor materials based on fused ring units, the energy conversion efficiency of organic solar cells has increased rapidly. This type of small molecule receptor material has strong absorption in the visible light region, and through rational molecular design, the absorption spectrum of this type of receptor material can be extended to the near...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/42H01L51/46
CPCC08G61/126C08G2261/124C08G2261/1426C08G2261/146C08G2261/3223C08G2261/122C08G2261/414C08G2261/91C08G2261/18H10K85/113H10K85/151H10K30/00Y02E10/549
Inventor 李淼淼耿延候王琪
Owner TIANJIN UNIV
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