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Diacenaphthyl quinone sulfide, preparation method and application thereof

A bisacenaphthenequinone-based sulfide and application technology are applied in the field of materials, and can solve the problems of unsatisfactory effect, low energy level of the lowest empty orbit, low short-circuit current of photovoltaic cells, etc., so as to increase the contact area, improve the short-circuit current, The effect of shortening the diffusion distance

Inactive Publication Date: 2015-12-30
NANJING UNIV OF INFORMATION SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For the planar π-conjugated electron donor compound TBP (Tetrabenzylporphrine, tetrabenzoporphrine), PCBM has two major disadvantages: 1. The lowest empty orbital energy level of PCBM is too low (-4.1eV); 2. The composition Photovoltaic battery short circuit current is low
However, existing electron acceptor materials do not match well with TBP

Method used

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  • Diacenaphthyl quinone sulfide, preparation method and application thereof
  • Diacenaphthyl quinone sulfide, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Step 1: Add acenaphthylquinone (7.29g, 40.0mmol) into 14.6mL of liquid bromine, heat to reflux for substitution reaction; after the substitution reaction time reaches 2 hours, distill off the liquid bromine, wash with hot water to remove residual bromine, and obtain 9.50g Yellow solid, yield 91.0%. The H spectrum data of this yellow solid is 1 HNMR (CDCl 3 ):δ=8.49(d,J=8.4Hz,2H);8.18(d,J=7.0Hz,2H);8.12(d,J=8.4Hz,2H);8.10–7.90(m,2H), MS (FI): 260.1, 262.1 (M+), elemental analysis (C 12 h 5 o 2 Br): Calcd. C, 55.21; H, 1.93. Found: C, 55.27; H, 1.94. The yellow solid was proved to be 5-bromoacenaphthoquinone.

[0026] Step 2: 5-bromoacenaphthenequinone (3.65g, 14.0mmol) was added in n-butanol, 105 o Stir at C until completely dissolved, then add Na 2 S (1.09g, 14mmol), the control reaction temperature is 105 o C, reacted under stirring for 5 hours, cooled, filtered to collect the precipitate, washed with hot water (75-90°C), and then washed with ethanol to obtain...

Embodiment 2

[0028] Step 1: Add acenaphthylquinone (7.29g, 40.0mmol) into 11mL of liquid bromine, heat to reflux for substitution reaction; after the substitution reaction time reaches 2 hours, distill off the liquid bromine, wash with hot water to remove residual bromine, and obtain 8.64g of yellow Solid, 82.8% yield. The H spectrum data of this yellow solid is 1 HNMR (CDCl 3 ):δ=8.49(d,J=8.4Hz,2H);8.18(d,J=7.0Hz,2H);8.12(d,J=8.4Hz,2H);8.10–7.90(m,2H), MS (FI): 260.1, 262.1 (M+), elemental analysis (C 12 h 5 o 2 Br): Calculated value: C, 55.21; H, 1.93. Measured value: C, 55.27; H, 1.94. The yellow solid was proved to be 5-bromoacenaphthylquinone.

[0029] Step 2: 5-bromoacenaphthenequinone (3.65g, 14.0mmol) was added in n-butanol, 110 o Stir at C until completely dissolved, then add Na 2 S (1.09g, 14mmol), the control reaction temperature is 110 o C, reacted under stirring for 5 hours, cooled, filtered to collect the precipitate, washed with hot water (75-90°C), and then washed w...

Embodiment 3

[0031] Step 1: Add acenaphthylquinone (7.29g, 40.0mmol) into 21.8mL of liquid bromine, heat to reflux for substitution reaction; the substitution reaction time reaches 2 hours, distill off the liquid bromine, wash with hot water to remove residual bromine, and obtain 8.64g of yellow Solid, 82.8% yield. The H spectrum data of this yellow solid is 1 HNMR (CDCl 3 ):δ=8.49(d,J=8.4Hz,2H);8.18(d,J=7.0Hz,2H);8.12(d,J=8.4Hz,2H);8.10–7.90(m,2H), MS (FI): 260.1, 262.1 (M+), elemental analysis (C 12 h 5 o 2 Br): Calculated value: C, 55.21; H, 1.93. Measured value: C, 55.27; H, 1.94. The yellow solid was proved to be 5-bromoacenaphthenequinone.

[0032]Step 2: 5-bromoacenaphthenequinone (3.65g, 14.0mmol) was added to a sufficient amount of n-butanol, 118 o Stir at C until completely dissolved, then add Na 2 S (1.09g, 14mmol), the control reaction temperature is 118 o C, reacted under stirring for 5 hours, cooled, filtered to collect the precipitate, washed with hot water (75-90°C)...

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Abstract

The invention provides diacenaphthequinone thioether and a preparation method thereof, relating to the field of materials. The preparation method of diacenaphthequinone thioether comprises the steps of performing a substitution reaction between acenaphthequinone and liquid bromine to obtain 5-bromoacenaphthequinone; enabling the 5-bromoacenaphthequinone to react with Na2S to obtain diacenaphthequinone thioether. The diacenaphthequinone thioether is a plane-conjugated organic molecule, thus the transfer of electrons among molecules is facilitated, the diffusion distance of excitons is shortened, the short-circuit current of a prepared heterojunction photovoltaic cell is increased, and the photoelectric conversion rate of the photovoltaic cell is improved. The preparation method of the diacenaphthequinone thioether provided by the invention is simple in process and environment-friendly and has high yield and few byproducts. The diacenaphthequinone thioether is used as a receptor material of the photovoltaic cell, and the matching effect with the electron receptor material TBP (tetrabenzylporphrine) is relatively good; the photovoltaic cell prepared from the compound and the TBP material has relatively high short-circuit current.

Description

technical field [0001] The invention relates to the field of materials, in particular to a diacenaphthyl quinone sulfide and a preparation method thereof. Background technique [0002] Compared with silicon photovoltaic cells, organic photovoltaic cells have the characteristics of low cost, light weight, small size, easy processing, good flexibility, and suitable for processing into large-area flat-panel devices. Improving the photoelectric conversion rate is the most important issue facing organic photovoltaic cells. According to the current energy supply situation, if the photoelectric conversion rate of organic photovoltaic cells is increased to 10%, it will have a price advantage and a broad application market. Therefore, it is of practical significance to develop low-cost organic / polymer photovoltaic cells. The main reason hindering the large-scale application of organic / polymer photovoltaic cells is: the photoelectric conversion rate of organic / polymer photovoltaic c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C323/22C07C319/14H01L51/46
CPCY02E10/549
Inventor 张超智胡鹏李世娟沈丹
Owner NANJING UNIV OF INFORMATION SCI & TECH