CN109134283B - Organic small-molecule hole transport material, preparation method and perovskite solar cell - Google Patents
Organic small-molecule hole transport material, preparation method and perovskite solar cell Download PDFInfo
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Abstract
The invention belongs to the technical field of photoelectric materials, and particularly relates to an organic small-molecule hole transport material, a preparation method and a perovskite solar cell. The material is Bp-OMe or Py-OMe. The method comprises the following steps: adding reactants into a reaction container under the atmosphere of protective gas, then adding tetrahydrofuran and water, carrying out bubbling for deoxygenation, and then heating and refluxing for 18-24 hours to obtain a mixture; cooling to room temperature, extracting the mixture with dichloromethane, and drying an organic layer to obtain an organic solution; and (3) carrying out rotary evaporation on the organic solution to remove the solvent to obtain a crude product, recrystallizing the crude product by using dichloromethane and methanol, and carrying out suction filtration to obtain a target product. The material has high hole mobility; the method has lower cost and simple preparation process; the material is applied to the perovskite solar cell, and the photoelectric conversion efficiency is high.
Description
Technical Field
The invention belongs to the technical field of photoelectric materials, and particularly relates to an organic small-molecule hole transport material, a preparation method and a perovskite solar cell.
Background
The arylamine organic micromolecules such as 2,2',7,7' -tetra [ N, N-di (4-methoxyphenyl) amino ] -9,9' -spirobifluorene (spiro-OMeTAD) are used as organic hole transport layer materials, and the stability, the efficiency and the service life of the organic-inorganic hybrid perovskite solar cell are greatly improved. However, the industrialization of perovskite solar cells based on the spiro-OMeTAD molecules is limited by the defects of long synthesis period, low yield, high cost and the like, and the photoelectric conversion efficiency of the perovskite solar cells taking the material as a hole transport layer basically reaches the upper limit. The novel hole transport material with different structures continuously emerges by taking triarylamine or carbazole as a basic electron supply group and biphenyl, indole, thiophene, pyrene and the like as a core skeleton or a connecting bridge group, improves the photoelectric conversion efficiency of the perovskite solar cell to a certain extent compared with a spiro-OMeTAD molecule, and obviously reduces the cost. Therefore, the novel organic micromolecules which can be used as hole transport materials are designed and synthesized, and the organic micromolecules are applied to the perovskite solar cell, so that the efficiency and the service life of the cell are expected to be further improved, the cell structure is optimized, the cost is reduced, and large-area production and industrialization are realized; has important scientific significance for solving the problems of energy shortage and environment.
Disclosure of Invention
In view of the above, the present invention aims to provide an organic small molecule hole transport material, which has high hole mobility; the second purpose of the invention is to provide a preparation method of the organic small molecule hole transport material, which is simple to operate and easy to realize industrialization; it is a further object of the present invention to provide a perovskite solar cell having a high photoelectric conversion efficiency.
An organic small molecule hole transport material, wherein the structural formula of the material is as follows:
wherein the content of the first and second substances,
is composed of
The invention relates to a preparation method of an organic small molecule hole transport material, which comprises the following steps:
when in use
Is composed of
The method comprises the following steps:
the chemical reaction equation is as follows:
under the atmosphere of protective gas, 3,5, 5-tetrabromobiphenyl (Bp-4Br), 4-boric acid ester-4 ',4' -dimethoxy triphenylamine and Pd (PPh)3)4，K2CO3Adding the mixture into a reaction vessel, adding Tetrahydrofuran (THF) and water serving as solvents, carrying out bubbling deoxygenation, and then heating and refluxing for 18-24 hours to obtain a mixture; cooling to room temperature, extracting the mixture with dichloromethane, drying an organic layer, performing rotary evaporation to obtain a crude product, recrystallizing the crude product with dichloromethane and methanol, and performing suction filtration to obtain a target product;
when in use
Is composed of
The method comprises the following steps:
the chemical reaction equation is as follows:
under the atmosphere of protective gas, 1,3,6, 8-tetrabromopyrene (Py-4Br), 4-borate-4 ',4' -dimethoxy triphenylamine and Pd (PPh)3)4，K2CO3Adding the mixture into a reaction vessel, adding THF (tetrahydrofuran) and water serving as solvents, carrying out bubbling deoxygenation, and heating and refluxing for 18-24 hours to obtain a mixture; and cooling to room temperature, extracting the mixture by using dichloromethane, drying an organic layer, carrying out rotary evaporation to obtain a crude product, recrystallizing the crude product by using dichloromethane and methanol, and carrying out suction filtration to obtain a target product.
Preferably, Bp-4Br, 4-boronate-4 ',4' -dimethoxytriphenylamine, Pd (PPh)3)4、K2CO3The molar using amount ratio of (1: 5:0.1: 4); py-4Br, 4-borate-4 ',4' -dimethoxytriphenylamine, Pd (P)Ph3)4、K2CO3The molar ratio of (A) to (B) is 1:5:0.1: 4.
Preferably, the protective gas is nitrogen or an inert gas.
Preferably, the bubbling oxygen removal time is 10-15 min.
Preferably, the volume ratio of THF to water is 10: 1.
Preferably, the mixture is heated to 90-100 ℃ for reflux.
Preferably, the organic layer is over anhydrous MgSO4And (5) drying.
An n-i-p type perovskite solar cell, wherein a hole transport layer of the cell adopts the organic micromolecule hole transport material.
Preferably, the thickness of the hole transport layer is 120-160 nm.
Has the advantages that:
the organic micromolecule hole transport material has high hole mobility, has the characteristics of low price, easiness in synthesis, lower cost, simplicity in preparation and process flow and the like, is applied to perovskite solar cells, is high in photoelectric conversion efficiency, and has huge research and commercial popularization values.
Drawings
FIG. 1 is a schematic structural view of a Scanning Electron Microscope (SEM) of a perovskite solar cell provided by the invention;
fig. 2 is a voltage-current graph of the perovskite solar cell obtained in examples 3 and 4 of the present invention.
Detailed Description
The following will clearly and completely describe in conjunction with the technical solutions of the embodiments of the present invention, and all other embodiments obtained by a person of ordinary skill in the art without creative efforts based on the embodiments of the present invention belong to the protection scope of the present invention.
In the following examples, the basic chemical reagents used were obtained from Okay technologies, Inc. of Beijing.
(1) High resolution mass spectrometry: the high-resolution mass spectrum data of the invention is measured by a Bruker MALDI-solariX mass spectrometer;
(2) nuclear magnetic hydrogen spectrum: the nuclear magnetic hydrogen spectrum data of the invention is measured by a Bruker Advance nuclear magnetism instrument, the resolution ratio is 400MHz, and the deuterated reagent is deuterated dimethyl sulfoxide [ (CD)3)2SO]；
(3) Nuclear magnetic carbon spectrum: the nuclear magnetic carbon spectrum data of the invention is measured by a Bruker Advance nuclear magnetic instrument, the resolution ratio is 400MHz, and the deuterated reagent is deuterated dimethyl sulfoxide [ (CD)3)2SO]；
(4) Voltage-current (J-V) curve of perovskite solar cell: the J-V curve of the present invention was measured by a solar simulator Enli technology Co., Ltd and a semiconductor tester (keitheley 2400) in which the solar simulator illumination output was 100mA/cm2(AM 1.5G)；
(5) Material Hole mobility (Hole mobility): the hole mobility of the material is obtained by testing a space-charge-limited current (SCLC) method and calculating according to the Mott-Gurney law.
In the embodiment of the invention, the device structure of the n-i-p type perovskite solar cell comprises a conductive substrate, an electron transport layer, a perovskite photoactive layer, a hole transport layer and a metal electrode from bottom to top in sequence as shown in fig. 1.
The conductive substrate is a substrate known to those skilled in the art, and is not particularly limited, such as ITO glass, flexible PET or PEN, and in the present invention, ITO glass.
The electron transport layer is not particularly limited as long as it is known to those skilled in the art, and may be, for example, SnO2、TiO2、PC61BM、PC71BM or ZnO, in the present invention SnO2。
The perovskite photoactive layer is a photoactive layer known to those skilled in the art, and is not particularly limited, and in the present invention, has the following chemical Formula (FAPBI)3)0.85(MAPbBr3)0.15(MA: methylamine, FA: formamidine) as the perovskite photoactive layer.
The metal electrode is a metal electrode known to those skilled in the art, and is not particularly limited, such as gold, silver, magnesium, aluminum or calcium, in the present invention, gold, and the thickness of the metal electrode is 80-120 nm.
The preparation method of the perovskite battery is a preparation method well known to those skilled in the art, and is not particularly limited.
Example 1
A preparation method of an organic small molecule hole transport material comprises the following steps:
the chemical reaction equation is as follows:
bp-4Br (235.0mg, 0.50mmol), 4-boronate-4 ',4' -dimethoxytriphenylamine (1.08g, 2.50mmol), Pd (PPh) under nitrogen atmosphere3)4(57.8mg,0.05mmol)，K2CO3(148.0mg,2.0mmol) was added to a dry Schlenk reaction flask, 20mL THF and 2.0mL water were added, nitrogen bubbled for 10min, and heated to 90 ℃ under nitrogen at reflux for 18 h; cooled to room temperature, the mixture was extracted with dichloromethane (20 mL. times.3), and the resulting organic layer was extracted with anhydrous MgSO4Drying; the solvent was removed by rotary evaporation to give a crude product, which was purified by recrystallization (50mL of dichloromethane was dissolved and 50mL of methanol was added to precipitate a solid) and suction filtered to give the desired product as a white solid (0.58g, yield 85%).
And (4) carrying out structural characterization on the obtained target product by adopting a high-resolution mass spectrometry, wherein the result of the high-resolution mass spectrometry is 1367.5791.
Performing structural characterization on the obtained target product by adopting a nuclear magnetic resonance analysis method, wherein the nuclear magnetic resonance characterization data is as follows:
1H NMR(400MHz,(CD3)2SO)/ppm:7.84(s,4H),7.75(s,2H),7.67(d,J＝8.8Hz,8H),7.05(d,J＝8.8Hz,16H),6.92(d,J＝8.8Hz,16H),6.85(d,J＝8.8Hz,8H),3.74(s,24H)；
13C NMR(400MHz,(CD3)2SO)/ppm:155.8,148.0,141.6,141.1,140.0,131.7,127.7,126.7,123.1,122.9,119.5,119.2,114.9,55.2。
experimental results show that the target product prepared by the embodiment is Bp-OMe. The calculation result shows that the Bp-OMe hole mobility is 1.251 multiplied by 10-3cm2·V-1·s-1。
Example 2
A preparation method of an organic small molecule hole transport material comprises the following steps:
the chemical reaction equation is as follows:
under a nitrogen atmosphere, Py-4Br (258.9mg, 0.5mmol), 4-boronate-4 ',4' -dimethoxytriphenylamine (1.08g, 2.5mmol), Pd (PPh)3)4(57.8mg,0.05mmol)，K2CO3(148.0mg,2.0mmol) was added to a dry Schlenk reaction flask, 20mL THF and 2.0mL water were added, nitrogen bubbled for 10min, and heated to 90 ℃ under nitrogen at reflux for 18 h; cooled to room temperature, the mixture was extracted with dichloromethane (20 mL. times.3), and the resulting organic layer was extracted with anhydrous MgSO4Drying; the solvent was removed by rotary evaporation to give a crude product, which was purified by recrystallization (50mL of dichloromethane was dissolved and 50mL of methanol was added to precipitate a solid) and suction filtered to give the desired product as a bright yellow solid (0.63g, 89% yield).
And (4) carrying out structural characterization on the obtained target product by adopting a high-resolution mass spectrometry, wherein the result of the high-resolution mass spectrometry is 1415.5832.
Performing structural characterization on the obtained target product by adopting a nuclear magnetic resonance analysis method, wherein the nuclear magnetic resonance characterization data is as follows:
1H NMR(400MHz,CD2Cl2)/ppm:8.16(s,4H),7.89(s,2H),7.39(d,J＝8.4Hz,8H),7.07(d,J＝8.8Hz,16H),6.98(d,J＝8.4Hz,8H),6.80(d,J＝8.8Hz,16H),3.72(s,24H)；
13C NMR(400MHz,CD2Cl2)/ppm:155.4,147.4,140.1,136.2,132.1,130.4,129.1,128.6,127.0,126.0,124.2,119.2,113.9,54.7。
experiment ofThe results show that the target product prepared in this example was Py-OMe. The Py-OMe hole mobility was calculated to be 4.443X 10-3cm2·V-1·s-1。
Example 3
And ultrasonically cleaning the ITO transparent conductive glass with the surface etched with patterns for 30min by using a cleaning agent, deionized water, isopropanol, acetone and ethanol in sequence, drying, and treating for 30min by using an ultraviolet ozone cleaning instrument. Suspension coating SnO on ITO substrate2Solution, SnO2Solution formulation SnO2The volume ratio of stock solution to water is 1:5, the spin coating condition is 3000r/30s, the annealing is carried out for 30min at the temperature of 150 ℃ on a constant temperature hot table, and SnO2The thickness of the layer is about 30 nm. Secondly, spin-coating a perovskite precursor solution by a one-step method to prepare a perovskite photoactive layer, annealing at 100 ℃ for 30min, wherein the solution formula is as follows: 461mg PbI2And 160mg of iodomethylamine dissolved in 600 μ L N, N-Dimethylformamide (DMF) solvent, spin coating conditions 4000r/25s, and rapidly washing the spinning substrate with 2mL of diethyl ether within 2s before discoloration of the perovskite photoactive layer, which has a thickness of about 600 nm. Then, spin coating a hole transport material on the surface of the perovskite photoactive layer, wherein the solution formula is as follows: 20mmol of Bp-OMe prepared in example 1 were dissolved in 1mL of chlorobenzene solution under spin-coating conditions of 3000r/30s and a hole transport layer having a thickness of about 120 nm. And finally, carrying out vacuum evaporation on an Au electrode with the thickness of 80-120 nm to obtain the n-i-p type perovskite solar cell.
The illumination intensity is 100mW/cm2The voltage-current curve of the n-i-p type perovskite solar cell device is tested under the irradiation of simulated sunlight by the AM 1.5 shown in figure 2, the voltage is reversely swept from 1.2 to-0.2V, and the open-circuit voltage is 0.98V, and the short-circuit current density is 21.93mA/cm2The fill factor was 0.70 and the energy conversion efficiency was 15.06%. Experimental results show that the Bp-OMe serving as a hole transport material is applied to the perovskite solar cell and can obtain higher photoelectric conversion efficiency.
Example 4
Sequentially ultrasonically cleaning ITO transparent conductive glass with patterns etched on the surface for 30min by using a cleaning agent, deionized water, isopropanol, acetone and ethanol, drying, and then usingTreating with ultraviolet ozone cleaning instrument for 30 min. Suspension coating SnO on ITO substrate2Solution, SnO2Solution formulation SnO2The volume ratio of stock solution to water is 1:5, the spin coating condition is 3000r/30s, the annealing is carried out for 30min at the temperature of 150 ℃ on a constant temperature hot table, and SnO2The thickness of the layer is about 30 nm. Secondly, spin-coating a perovskite precursor solution by a one-step method to prepare a perovskite photoactive layer, annealing at 100 ℃ for 30min, wherein the solution formula is as follows: 461mg PbI2And 160mg of iodomethylamine dissolved in 600 μ L of DMF solvent, spin coating conditions 4000r/25s, rapidly washing the spinning substrate with 2mL of diethyl ether within 2s before discoloration of the perovskite photoactive layer, the thickness of the perovskite photoactive layer being about 600 nm. Then, spin coating a hole transport material on the surface of the perovskite photoactive layer, wherein the solution formula is as follows: 20mmol of the organic micromolecule hole transport material Py-OMe prepared in the example 2 is dissolved in 1mL of chlorobenzene solution, the spin coating condition is 3000r/30s, and the thickness of the hole transport layer is about 120 nm. And finally, carrying out vacuum evaporation on an Au electrode with the thickness of 80-120 nm to obtain the n-i-p type perovskite solar cell.
The illumination intensity is 100mW/cm2The voltage-current curve of the n-i-p type perovskite solar cell device is tested under the irradiation of simulated sunlight by the AM 1.5, as shown in figure 2, the voltage is reversely swept from 1.2 to-0.2V, and the open-circuit voltage is 1.11V, and the short-circuit current density is 22.82mA/cm2The fill factor was 0.76 and the energy conversion efficiency was 19.28%. Experimental results show that the Py-OMe serving as a hole transport material is applied to the perovskite solar cell and can obtain higher photoelectric conversion efficiency.
The invention includes, but is not limited to, the above embodiments, and any equivalent substitutions or partial modifications made under the spirit and principle of the invention are deemed to be within the scope of the invention.
Claims (10)
1. An organic small molecule hole transport material, characterized in that: the structural formula of the material is as follows:
wherein the content of the first and second substances,
is composed of
2. A method for preparing the organic small molecule hole transport material of claim 1, wherein the method comprises the following steps: the method comprises the following steps:
when in use
Is composed of
The method comprises the following steps:
under the protective gas atmosphere, 3,5, 5-tetrabromobiphenyl, 4-boric acid ester-4 ',4' -dimethoxy triphenylamine and Pd (PPh)3)4，K2CO3Adding the mixture into a reaction container, adding THF (tetrahydrofuran) and water, carrying out bubbling deoxygenation, and then heating and refluxing for 18-24 hours to obtain a mixture; cooling to room temperature, extracting the mixture with dichloromethane, drying an organic layer, performing rotary evaporation to obtain a crude product, recrystallizing the crude product with dichloromethane and methanol, and performing suction filtration to obtain a target product;
when in use
Or
The method comprises the following steps:
under the atmosphere of protective gas, 1,3,6, 8-tetrabromopyrene, 4-boric acid ester-4 ',4' -dimethoxy triphenylamine and Pd (PPh)3)4，K2CO3Adding the mixture into a reaction container, adding THF (tetrahydrofuran) and water, carrying out bubbling deoxygenation, and then heating and refluxing for 18-24 hours to obtain a mixture; cooling to room temperature, extracting the mixture with dichloromethane, drying the organic layer, and rotary evaporating to obtain crude productRecrystallizing the product by using dichloromethane and methanol, and filtering to obtain a target product.
3. The method for preparing an organic small molecule hole transport material according to claim 2, wherein: 3,3,5, 5-tetrabromobiphenyl, 4-borate-4 ',4' -dimethoxytriphenylamine and Pd (PPh)3)4、K2CO3The molar using amount ratio of (1: 5:0.1: 4); 1,3,6, 8-tetrabromopyrene, 4-borate-4 ',4' -dimethoxytriphenylamine and Pd (PPh)3)4、K2CO3The molar ratio of (A) to (B) is 1:5:0.1: 4.
4. The method for preparing an organic small molecule hole transport material according to claim 2, wherein: the protective gas is nitrogen or inert gas.
5. The method for preparing an organic small molecule hole transport material according to claim 2, wherein: and the bubbling deoxidization time is 10-15 min.
6. The method for preparing an organic small molecule hole transport material according to claim 2, wherein: the volume ratio of THF to water was 10: 1.
7. The method for preparing an organic small molecule hole transport material according to claim 2, wherein: heating to 90-100 ℃ for reflux.
8. The method for preparing an organic small molecule hole transport material according to claim 2, wherein: the organic layer was dried over anhydrous MgSO4And (5) drying.
9. An n-i-p type perovskite solar cell, characterized in that: the hole transport layer of the battery adopts an organic small molecule hole transport material as claimed in claim 1.
10. An n-i-p type perovskite solar cell as claimed in claim 9, wherein: the thickness of the hole transport layer is 120-160 nm.
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| CN111233681B (en) * | 2020-03-30 | 2021-02-02 | 中国科学院化学研究所 | Star-shaped tetramine pyrene compound, preparation method and application thereof |
| CN112279775B (en) * | 2020-10-28 | 2021-08-31 | 中国科学院化学研究所 | Pyrene-bridged organic amine hole transport material and preparation method and application thereof |
| CN113087726A (en) * | 2021-02-24 | 2021-07-09 | 浙江大学 | Arylamine organic semiconductor material and application thereof in photoelectric device |
| CN113185449B (en) * | 2021-03-12 | 2023-09-19 | 云南大学 | Synthesis of carbazole-based organic micromolecular hole transport material and application of carbazole-based organic micromolecular hole transport material in perovskite solar cell |
| CN113956220B (en) * | 2021-10-19 | 2023-04-07 | 南京工业大学 | Undoped hole transport material and preparation method thereof, perovskite solar cell and preparation method |
| CN114315856B (en) * | 2021-12-20 | 2023-04-07 | 淮阴工学院 | Doping-free hole transport material containing phenazine dithiophene and preparation method and application thereof |
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