CN110563745B - Micromolecule hole transport material for organic solar cell and preparation method thereof - Google Patents
Micromolecule hole transport material for organic solar cell and preparation method thereof Download PDFInfo
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Abstract
The invention relates to a micromolecule hole transport material for an organic solar cell and a preparation method thereof, wherein the preparation method specifically comprises the steps of carrying out addition reaction on cyclopentadithiophene and 1, 4-butanesultone to obtain an intermediate product, then carrying out reaction on the intermediate product and N-bromosuccinimide to obtain a brominated intermediate product, and carrying out reaction on the brominated intermediate product and 4-biphenylboronic acid to obtain the micromolecule hole transport material 2, 6-di-biphenyl-4, 4-di-potassium butylsulfonate-cyclopentadithiophene. The micromolecular hole transport material 2, 6-di-biphenyl-4, 4-di-butylpotassium sulfonate-cyclopentadithiophene prepared by the invention is used for the hole transport layer of the organic solar cell, and has the advantages of simple preparation process, high purity, high photoelectric conversion efficiency and the like.
Description
Technical Field
The invention relates to a micromolecule hole transport material for an organic solar cell and a preparation method thereof, and particularly belongs to the technical field of photoelectric materials.
Background
The organic solar cell is a new generation of photovoltaic power generation technology, has the outstanding advantages of low cost, light weight, flexibility, strong designability and the like, and has wide application field. The hole transport layer is an important component of the organic solar cell, and can regulate and control energy level matching between the anode and the active layer, improve the efficiency of hole transport and collection, and improve physical contact between the anode and the active layer, thereby obviously improving the photoelectric conversion efficiency and stability of the organic solar cell.
At present, most hole transport materials of organic solar cells are polymers, and the defects of complex preparation process, low photoelectric conversion efficiency and the like exist. For example, the most commonly used polymer hole transport material at present, poly (3, 4-ethylenedioxythiophene): polystyrene sulfonate (PEDOT: PSS), is prepared by the following steps: dissolving sodium poly (p-styrenesulfonate) in a certain amount of deionized water, dropwise adding a 3, 4-ethylenedioxythiophene monomer into the deionized water, slowly stirring for 5 minutes, dropwise adding hydrochloric acid to control the pH value of the system to be 2-3, slowly dropwise adding a mixed solution of ammonium persulfate and ferric sulfate, quickly stirring to react for 24 hours, and then respectively exchanging inorganic salt ions for 4 hours by using anion exchange resin and cation exchange resin to obtain a PEDOT/PSS dark blue solution. Wherein the molar ratio of PSS to EDOT is 2:1, the molar ratio of ammonium persulfate to EDOT is 1.5:1, and the molar ratio of ferric sulfate to EDOT is 0.002: 1. As mentioned above, the preparation process of PEDOT and PSS involves many processes such as polymerization and ion exchange, and is complicated and tedious. In addition, the molecular weight and the distribution of PEDOT and PSS are greatly influenced by the preparation process and have poor repeatability.
The water/alcohol-soluble conjugated polyelectrolyte is also a commonly used organic solar cell hole transport material at present, such as poly (4, 4-bis-butyl potassium sulfonate-alt-benzothiadiazole). The poly (4, 4-potassium dibutylsulfonate-alt-benzothiadiazole) adopts a free radical polymerization mechanism, needs to be prepared under the anhydrous and oxygen-free conditions, and has harsh process conditions. In addition, there are also disadvantages that the molecular weight and the distribution thereof are greatly affected by the production process, and that the molecular weight and the distribution thereof have poor reproducibility.
The invention provides a micromolecule hole transport material aiming at the problems of complicated preparation process, poor repeatability and the like of a polymer hole transport material. The hole transport material provided by the invention has the characteristics of simple preparation process, no need of an ion exchange column and no need of anhydrous and oxygen-free preparation conditions. In addition, the micromolecule hole transport material provided by the invention also has excellent water solubility and film forming property, can be processed by aqueous solution at room temperature, and is green and environment-friendly. Test results show that the HOMO energy level of the small molecule hole transport material provided by the invention is-5.10 eV, the work function of the modified ITO is-5.05 eV, and the energy level requirement of the small molecule hole transport material as a hole transport layer of an organic solar cell is completely met.
Disclosure of Invention
Aiming at the problems of complex and fussy preparation process and poor repeatability of the existing polymer hole transport material for the organic solar cell, the invention aims to provide a micromolecule hole transport material which has simple preparation process, good repeatability, high purity and higher photoelectric conversion efficiency.
The molecular structural formula of the micromolecule hole transport material for the organic solar cell is as follows:
the preparation method of the micromolecule hole transport material comprises the following steps:
step 1: adding 1.0 mol part of cyclopentadithiophene and 20.0 ml of dimethyl sulfoxide into a glass three-necked bottle, mechanically stirring for 20 minutes at room temperature, then adding 20.0 ml of 1.0 mol/L potassium hydroxide aqueous solution and 2.0 mol part of 1, 4-butanesultone, mechanically stirring for reaction for 2-3 hours at room temperature, then pouring reactants in the three-necked bottle into 100.0 ml of acetone, mechanically stirring for 30 minutes at room temperature, and performing suction filtration to obtain a solid intermediate product A;
step 2: adding 1.0 mol part of intermediate product A and 30.0 ml of N, N-dimethylformamide into a glass three-necked bottle, mechanically stirring for 20 minutes at room temperature, then adding 20.0 ml of N-bromosuccinimide and 20.0 ml of distilled water, mechanically stirring for reaction for 1.0 hour at room temperature, then pouring reactants in the three-necked bottle into 100.0 ml of acetone, mechanically stirring for 30 minutes at room temperature, and carrying out suction filtration to obtain a solid intermediate product B;
and step 3: 1.0 mol part of the intermediate product B, 2.0 mol parts of 4-biphenylboronic acid and 40.0 ml of N, N-dimethylformamide are added into a glass three-necked flask, the mixture is magnetically stirred for 20 minutes at room temperature, nitrogen with the flow rate of 1.0 liter/minute is introduced for 1.0 hour in a bubbling manner, then adding 0.04-0.05 mol part of tetratriphenylphosphine palladium and 10.0 ml of 2.0 mol/L potassium carbonate aqueous solution, heating the three-necked flask to 90-100 ℃ at a heating rate of 10 ℃/min, carrying out magnetic stirring reaction at a constant temperature of 90-100 ℃ for 24-36 hours, stopping the reaction, cooling to room temperature, pouring the reactants in the three-necked flask into 100.0 ml of acetone, mechanically stirring for 30 minutes at room temperature, and performing suction filtration to obtain a light yellow solid product 2, 6-di-biphenyl-4, 4-di-butyl potassium sulfonate-cyclopentadithiophene, namely the micromolecule hole transport material.
The invention has the beneficial effects that:
the preparation process of the micromolecular hole transport material 2, 6-di-biphenyl-4, 4-di-butylpotassium sulfonate-cyclopentadithiophene is simple, and the preparation condition of no need of passing through an ion exchange column or no need of water and oxygen is not needed.
The micromolecular hole transport material 2, 6-di-biphenyl-4, 4-di-butyl potassium sulfonate-cyclopentadithiophene has excellent water solubility and film forming property, can be processed by aqueous solution at room temperature, and is green and environment-friendly.
The HOMO energy level of the micromolecule hole transport material 2, 6-di-biphenyl-4, 4-di-butylpotassium sulfonate-cyclopentadithiophene is-5.10 eV, the work function of the modified ITO is-5.05 eV, and the energy level requirement of the micromolecule hole transport material as a hole transport layer of an organic solar cell is completely met.
Drawings
Fig. 1 is a molecular structural formula of a small molecule hole transport material for an organic solar cell.
Detailed Description
The present invention is described by the following examples, but the present invention is not limited to the following examples, and variations and implementations are included in the technical scope of the present invention without departing from the spirit of the invention described before and after.
Example 1
Adding 1.0 mol part of cyclopentadithiophene and 20.0 ml of dimethyl sulfoxide into a glass three-necked bottle, mechanically stirring for 20 minutes at room temperature, then adding 20.0 ml of 1.0 mol/L potassium hydroxide aqueous solution and 2.0 mol part of 1, 4-butanesultone into the glass three-necked bottle, mechanically stirring for 2.0 hours at room temperature, then pouring all reactants in the glass three-necked bottle into 100.0 ml of acetone, mechanically stirring for 30 minutes at room temperature, and then carrying out suction filtration to obtain a solid intermediate product A;
adding 1.0 mol part of the intermediate product A and 30.0 ml of N, N-dimethylformamide into a glass three-necked bottle, mechanically stirring for 20 minutes at room temperature, then adding 20.0 ml of N-bromosuccinimide and 20.0 ml of distilled water into the glass three-necked bottle, mechanically stirring for 1.0 hour at room temperature, then pouring all reactants in the glass three-necked bottle into 100.0 ml of acetone, mechanically stirring for 30 minutes at room temperature, and then carrying out suction filtration to obtain a solid intermediate product B;
adding 1.0 mol part of intermediate product B, 2.0 mol part of 4-biphenylboronic acid and 40.0 ml of N, N-dimethylformamide into a glass three-necked bottle, magnetically stirring for 20 minutes at room temperature, introducing nitrogen with the flow rate of 1.0 liter/minute for 1.0 hour in a bubbling manner, then adding 0.04 mol part of tetratriphenylphosphine palladium and 10.0 ml of 2.0 mol/liter potassium carbonate aqueous solution, heating the three-necked bottle to 90 ℃ at the heating rate of 10 ℃/minute, magnetically stirring and reacting for 24.0 hours at the constant temperature of 90 ℃, stopping the reaction, cooling to room temperature, pouring all reactants in the three-necked bottle into 100.0 ml of acetone, mechanically stirring for 30 minutes, and carrying out suction filtration to obtain a light yellow solid product 2, 6-di-biphenyl-4, 4-di-butylpotassium sulfonate-cyclopentylthiophene.
Example 2
Adding 1.0 mol part of cyclopentadithiophene and 20.0 ml of dimethyl sulfoxide into a glass three-necked bottle, mechanically stirring for 20 minutes at room temperature, then adding 20.0 ml of 1.0 mol/L potassium hydroxide aqueous solution and 2.0 mol part of 1, 4-butanesultone into the glass three-necked bottle, mechanically stirring for 3.0 hours at room temperature, then pouring all reactants in the glass three-necked bottle into 100.0 ml of acetone, mechanically stirring for 30 minutes at room temperature, and then carrying out suction filtration to obtain a solid intermediate product A;
adding 1.0 mol part of the intermediate product A and 30.0 ml of N, N-dimethylformamide into a glass three-necked bottle, mechanically stirring for 20 minutes at room temperature, then adding 20.0 ml of N-bromosuccinimide and 20.0 ml of distilled water into the glass three-necked bottle, mechanically stirring for 1.0 hour at room temperature, then pouring all reactants in the glass three-necked bottle into 100.0 ml of acetone, mechanically stirring for 30 minutes at room temperature, and then carrying out suction filtration to obtain a solid intermediate product B;
adding 1.0 mol part of intermediate product B, 2.0 mol part of 4-biphenylboronic acid and 40.0 ml of N, N-dimethylformamide into a glass three-necked bottle, magnetically stirring for 20 minutes at room temperature, introducing nitrogen with the flow rate of 1.0 liter/minute for 1.0 hour in a bubbling manner, then adding 0.05 mol part of tetratriphenylphosphine palladium and 10.0 ml of 2.0 mol/liter potassium carbonate aqueous solution, heating the three-necked bottle to 100 ℃ at the heating rate of 10 ℃/minute, magnetically stirring for reaction for 36.0 hours at the constant temperature of 100 ℃, stopping the reaction, cooling to room temperature, pouring all reactants in the three-necked bottle into 100.0 ml of acetone, mechanically stirring for 30 minutes, and carrying out suction filtration to obtain a light yellow solid product 2, 6-di-biphenyl-4, 4-di-butylpotassium sulfonate-cyclopentylthiophene.
0.5 g of potassium 2, 6-bis-biphenyl-4, 4-dibutylsulfonate-cyclopentylthiophene from example 1 or example 2, respectively, was dissolved in 10.0 ml of water, mechanically stirred at room temperature for 20 minutes, and then the solution was passed through a 2 μm filter head to obtain a solution of potassium 2, 6-bis-biphenyl-4, 4-dibutylsulfonate-cyclopentylthiophene.
Using SevenGoTMpH-SG2 pH meter the pH of the test solution.
Hole mobility (μ) was tested for both examples using space charge limited current methodh). The device structure is as follows: indium tin oxide glass (ITO)/2, 6-bis-biphenyl-4, 4-di-butylsulfonic acid potassium-cyclopentadithiophene/gold (Au) prepared in example 1 or example 2. The spin coating conditions of the 2, 6-bis-biphenyl-4, 4-bis-butylsulfonic acid potassium-cyclopentadithiophene solution were 3000 revolutions for 30 seconds. The Au is processed by vacuum evaporation, and the evaporation thickness is 80 nanometers.
The photoelectric conversion efficiency of 2, 6-bis-biphenyl-4, 4-bis-butylpotassium sulfonate-cyclopentadithiophene was tested using a forward organic solar cell device. The device structure is as follows: ITO/Potassium 2, 6-bis-biphenyl-4, 4-di-butylsulfonate-cyclopentadithiophene/Poly [ [4, 8-bis [ (2-ethylhexyl) oxo-2, 6-bis-biphenyl-4, 4-di-butylsulfonate prepared in example 1 or example 2]Benzo [1,2-b:4,5-b']Dithiophene-2, 6-diyl]-alt- [ 3-fluoro-2- [ (2-ethylhexyl) carbonyl]Thieno [3,4-b]Thiophenediyl]](PTB7), and [6,6 ]]-phenyl C71 butyric acid methyl ester (PC)71BM) blended active layer/PFN/aluminum (Al). The spin coating conditions for 2, 6-bis-biphenyl-4, 4-bis-butylsulfonic acid potassium-cyclopentadithiophene were 3000 revolutions for 30 seconds. PTB7 and PC71The mass ratio of BM is 1: 1. The thickness of the PFN is 5-10 nanometers. Thickness of Al depositedIs 80 nm. For comparison, organic solar cells of the same construction were also fabricated using PEDOT: PSS 4083. The prepared organic solar cell was further tested for photoelectric conversion efficiency by a Keithley 2400 system. The photoelectric conversion efficiency is averaged by 5 cells to reduce errors.
The data such as the photoelectric conversion efficiency of the battery are shown in the table 1:
Claims (2)
1. a micromolecule hole transport material for an organic solar cell is characterized in that: the molecular structural formula of the micromolecular hole transport material is as follows:
2. a preparation method of a micromolecule hole transport material for an organic solar cell is characterized by comprising the following steps: the preparation method comprises the following steps:
step 1: adding 1.0 mol part of cyclopentadithiophene and 20.0 ml of dimethyl sulfoxide into a glass three-necked bottle, mechanically stirring for 20 minutes at room temperature, then adding 20.0 ml of 1.0 mol/L potassium hydroxide aqueous solution and 2.0 mol part of 1, 4-butanesultone, mechanically stirring for reaction for 2-3 hours at room temperature, then pouring reactants in the three-necked bottle into 100.0 ml of acetone, mechanically stirring for 30 minutes at room temperature, and performing suction filtration to obtain a solid intermediate product A;
step 2: adding 1.0 mol part of intermediate product A and 30.0 ml of N, N-dimethylformamide into a glass three-necked bottle, mechanically stirring for 20 minutes at room temperature, then adding 20.0 ml of N-bromosuccinimide and 20.0 ml of distilled water, mechanically stirring for reaction for 1.0 hour at room temperature, then pouring reactants in the three-necked bottle into 100.0 ml of acetone, mechanically stirring for 30 minutes at room temperature, and carrying out suction filtration to obtain a solid intermediate product B;
and step 3: 1.0 mol part of the intermediate product B, 2.0 mol parts of 4-biphenylboronic acid and 40.0 ml of N, N-dimethylformamide are added into a glass three-necked flask, the mixture is magnetically stirred for 20 minutes at room temperature, nitrogen with the flow rate of 1.0 liter/minute is introduced for 1.0 hour in a bubbling manner, then adding 0.04-0.05 mol part of tetratriphenylphosphine palladium and 10.0 ml of 2.0 mol/L potassium carbonate aqueous solution, heating the three-necked flask to 90-100 ℃ at a heating rate of 10 ℃/min, carrying out magnetic stirring reaction at a constant temperature of 90-100 ℃ for 24-36 hours, stopping the reaction, cooling to room temperature, pouring the reactants in the three-necked flask into 100.0 ml of acetone, mechanically stirring for 30 minutes at room temperature, and performing suction filtration to obtain a light yellow solid product 2, 6-di-biphenyl-4, 4-di-butyl potassium sulfonate-cyclopentadithiophene, namely the micromolecule hole transport material.
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| CN105720210A (en) * | 2014-12-23 | 2016-06-29 | 光州科学技术院 | P-doped conjugated small molecular electrolyte and organic electronic devices using the same |
| CN108341935A (en) * | 2018-04-11 | 2018-07-31 | 南昌航空大学 | A kind of organic solar batteries anode modification layer material and preparation method |
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