CN111153914B - Asymmetric hole transport material and preparation method and application thereof - Google Patents
Asymmetric hole transport material and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses an asymmetryThe hole transport material uses tetrathiophene pyrrole as molecular core, two sides separately use methoxy triphenylamine, indeno [1,2-b]Carbazole is a peripheral modifying group, the hole transport material of the invention can effectively cooperate with the peripheral modifying groups at two sides, and indeno [1,2-b]The rigidity and planarization space configuration of carbazole enhances the interaction between the molecules of the hole transport material, improves the conductivity and the hole mobility, and inhibits the recombination of interface carriers by utilizing the three-dimensional twisted space structure of methoxyl triphenylamine; in addition, the reduction of molecular symmetry can effectively improve the dissolution and film-forming properties of the material, and is beneficial to obtaining high-quality amorphous films. The asymmetric hole transport material is applied to perovskite solar cells, and the short-circuit photocurrent density of a cell device reaches 22.98 mA cm‑2The open-circuit voltage is 1.099V, the fill factor is 0.7923, the photoelectric conversion efficiency is as high as 20.01 percent, and the method has wide commercial application prospect.
Description
Technical Field
The invention belongs to the technical field of solar cells, and particularly relates to an asymmetric hole transport material and preparation and application thereof.
Background
As a new generation of photovoltaic technology, Perovskite Solar Cells (PSCs for short) have the advantages of simple preparation process, easily adjustable materials, low cost, and the like, and the latest certification efficiency has reached 25.2% (National Renewable Energy Laboratory, NREL, 2019). The hole transport layer is used as an important component of PSCs, plays a role in collecting photogenerated holes of the perovskite absorption layer and transporting the photogenerated holes to a counter electrode, effectively inhibits the recombination of device interface electrons, and plays a vital role in influencing the efficiency and stability of the battery. Currently, the most widely used and highly efficient hole transport material in perovskite solar cells is 2, 2', 7,7 ' -tetrakis [ N, N-bis (4-methoxyphenyl) amino ] -9,9 ' -spirobifluorene (Spiro-OMeTAD). However, the synthetic preparation cost of the Spiro-OMeTAD molecule is high, and the perovskite solar cell prepared from the Spiro-OMeTAD molecule has poor stability, so that the wide range of commercial applications of the Spiro-OMeTAD molecule is limited. Therefore, based on molecular engineering, it is important to develop a novel hole transport material that is efficient, stable, and inexpensive and can replace Spiro-OMeTAD.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide an asymmetric hole transport material, which can effectively cooperate with the advantages of different peripheral modifying groups at two sides and utilizes indeno (1, 2-b]The rigidity and planarization space configuration of carbazole enhances the interaction between the molecules of the hole transport material, improves the conductivity and the hole mobility, and inhibits the recombination of interface carriers by utilizing the three-dimensional twisted space structure of methoxyl triphenylamine; the invention also aims to provide a preparation method of the hole transport material and application of the hole transport material in a perovskite solar cell.
The invention is realized by the following technical scheme:
an asymmetric hole-transporting material is prepared from tetrathienopyrrole as molecular core, methoxy triphenylamine, indeno [1,2-b]Carbazole is a peripheral modifying group, and the chemical structural formula is as follows:
the invention further improves the scheme as follows:
a preparation method of an asymmetric hole transport material comprises the following steps:
s1: subjecting the compound of formula (1) and the compound of formula (2) to a Still coupling reaction to produce a compound of formula (3);
s2: carrying out coupling reaction on the compound shown in the formula (3) and bromomethoxytriphenylamine to generate a compound shown in a formula (4), namely an asymmetric hole transport material;
further, in said S1, the compound of formula (1) is subjected to a Still coupling reaction with the compound of formula (2) in toluene as a solvent under the catalysis of tetratriphenylphosphine palladium to generate the compound of formula (3), wherein the amount of each substance is calculated by the amount of substance, the compound of formula (1): a compound of formula (2): palladium tetratriphenylphosphine =1: 1-2: 0.01-0.2; the reaction time is 4-12 h.
Further, in the S2, reacting the compound of formula (3) with bromomethoxytriphenylamine in anhydrous N, N-dimethylformamide under the action of a palladium catalyst, an organophosphorus ligand, an organic acid and a base to obtain a compound of formula (4), wherein the amount of each substance is calculated by the amount of substance, the compound of formula (3): bromo methoxy triphenylamine: palladium catalyst: organophosphorus ligands: organic acid: alkali =1: 2-5: 0.01-0.2: 0.02-0.5: 0.2-1: 2-4.
Further, in S2, the palladium catalyst is one or a mixture of two or more of tris (dibenzylideneacetone) dipalladium, [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium and palladium acetate; the organophosphorus ligand is one or more of tri (o-methylphenyl) phosphorus, tri (m-methylphenyl) phosphorus, tri (p-methylphenyl) phosphorus, tricyclohexylphosphine, n-butyl di (1-adamantyl) phosphine or 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl; the organic acid is one or a mixture of pivalic acid and acetic acid; the alkali is one or more of sodium carbonate, potassium carbonate, sodium tert-butoxide or potassium tert-butoxide.
Further, each step of the method also comprises a separation and purification step.
The invention further improves the scheme as follows:
the asymmetric hole transport material is applied to the perovskite solar cell.
The invention has the beneficial effects that:
the asymmetric hole transport material is synthesized by a one-step method, has the advantages of simple synthesis route, low cost, easy separation and purification and suitability for mass preparation. The asymmetric hole transport material can effectively cooperate with different peripheral modification groups on two sides, and utilizes indeno [1,2-b]The rigidity and planarization space configuration of carbazole enhances the interaction between the molecules of the hole transport material, improves the conductivity and the hole mobility, and inhibits the recombination of interface carriers by utilizing the three-dimensional twisted space structure of methoxyl triphenylamine; the reduction of molecular symmetry can also effectively improve the dissolution and film-forming properties of the material, and is beneficial to obtaining high-quality amorphous films. The asymmetric hole transport material is applied to the perovskite solar cell, and the short-circuit photocurrent density reaches 22.98 mA cm-2The open-circuit voltage is 1.099V, the fill factor is 0.7923, and the photoelectric conversion efficiency is as high as 20.01%.
Drawings
FIG. 1 shows UV-visible absorption and fluorescence emission spectra of a hole transporting material (4);
FIG. 2 is a differential pulse voltammogram of the hole transport material (4);
FIG. 3 shows the stable fluorescence test of the hole transport material (4);
FIG. 4 is a schematic diagram of a perovskite solar cell structure prepared based on a hole transport material (4); in the figure: 1. the solar cell comprises a metal electrode, 2, a hole transport layer, 3, a perovskite photosensitive layer, 4, an electron transport layer, 5 and conductive glass;
FIG. 5 is an I-V plot of a perovskite solar cell prepared based on the hole transport material (4);
fig. 6 is an I-V plot of a perovskite solar cell prepared based on the hole transport material Spiro-OMeTAD.
Detailed Description
The present embodiment provides an asymmetric hole transport material having a chemical formula of formula (4):
the preparation method of the above hole transport material (compound of formula (4)) is as follows:
the compound of formula (1) used in this example was prepared and synthesized according to patent CN 201811021012.7; the compounds of the formula (2) are prepared and synthesized according to the documents Wang, J.; Zhang, H.; Wu, B.; Wang, Z.; Sun, Z.; Xue, S.; Wu, Y.; Hagfeldt, A.; Liang, M. Angew. chem. 2019, 58 (44), 15724-; other reagents are commercially available.
S1: subjecting the compound of formula (1) and the compound of formula (2) to a Still coupling reaction to produce a compound of formula (3);
the method specifically comprises the following steps: a50 mL three-necked round-bottomed flask was charged with the compound of formula (1) (2 mmol, 932 mg), the compound of formula (2) (2.2 mmol, 887 mg), tetrakistriphenylphosphine palladium (0.05 mmol, 58 mg), and 15 mL of toluene in this order under protection of argon; stirring the mixed solution, heating to 110 ℃, reacting for 8 hours, cooling to room temperature, adding water and dichloromethane for extraction, washing an organic phase for 3 times, drying with anhydrous magnesium sulfate, and distilling under reduced pressure to remove the solvent; the crude product was purified by column chromatography (eluent: petroleum ether/dichloromethane = 25/1-1/1) to give 902 mg of the compound of formula (3) as a dark yellow solid with a yield of 57%.1H NMR (400 MHz, CDCl3): δ 8.29 (s, 1H), 8.15 (s, 1H), 7.85 (d, J = 7.0 Hz, 1H), 7.70-7.65 (m, 3H), 7.60 (d, J = 7.6 Hz, 2H), 7.53 (d, J = 8.8 Hz, 2H), 7.49 (d, J = 7.0 Hz, 1H), 7.40-7.36 (m, 3 H), 7.23 (d, J = 8.8 Hz, 2H), 4.33 (t, J = 7.0 Hz, 2H), 4.15 (t, J = 6.8 Hz, 2H), 2.03-1.88 (m, 4H), 1.63 (s, 6H), 1.60-1.57 (m, 2H), 1.43-1.41 (m, 4H), 1.04 (t, J = 7.2 Hz, 3H), 0.96 (t, J = 6.8 Hz, 3H). HRMS (ESI) calcd for C48H43N2OS4 (M+H+): 791.2258, found: 791.2252.
S2: carrying out coupling reaction on the compound shown in the formula (3) and bromomethoxytriphenylamine to generate a compound shown in a formula (4), namely an asymmetric hole transport material;
the method specifically comprises the following steps: under the protection of argon, a compound (790 mg, 1 mmol) of the formula (3), bromomethoxytriphenylamine (575 mg, 1.5 mmol), potassium carbonate (207 mg, 1.5 mmol), palladium acetate (23 mg, 0.1 mmol), N-butyldi (1-adamantyl) phosphine (72 mg, 0.2 mmol), acetic acid (18 mg, 0.3 mmol) and anhydrous N, N-dimethylformamide (5 mL) are sequentially added into a dried Schlenk tube, and the reaction solution is heated to 150 ℃ and continuously stirred for reaction for 30 hours; cooling to room temperature, adding water for quenching, extracting by dichloromethane, washing an organic phase for three times, drying by anhydrous magnesium sulfate, and distilling under reduced pressure to remove the solvent; the crude product was purified by column chromatography (eluent: petroleum ether/dichloromethane = 15/1-1/1) to give 221 mg of the hole transport material (4) as an orange solid with a yield of 20.3%.1H NMR (400 MHz, d8-THF): δ 8.34(s, 1H), 8.26 (s, 1H), 7.88-7.70 (m, 5H), 7.64-7.48 (m, 4H), 7.39-7.21 (m, 6H), 7.06 (d, J = 8.6 Hz, 4H), 6.89-6.81 (m, 6H), 4.39 (t, J = 6.4 Hz, 2H), 4.15 (t, J = 6.0 Hz, 2H), 3.78 (s, 6H), 1.98-1.88 (m, 4H), 1.59 (s, 6H), 1.50-1.36 (m, 2H), 1.34-1.27 (m, 4H), 1.02-0.93 (m, 6H). 13C NMR (100 MHz, d8-THF): δ 157.2, 154.7, 152.6, 146.7, 143.6, 142.9, 142.6, 141.4, 139.3, 138.9, 138.7, 138.0, 137.8, 136.4, 133.0, 128.8, 128.7, 126.7, 125.0, 124.9, 124.8, 123.9, 123.6, 121.7, 121.3, 119.7, 118.4, 117.8, 116.5, 114.9, 113.7, 113.6, 112.5, 107.2, 98.2, 66.3, 52.8, 44.2, 42.4, 29.9, 27.6, 24.0, 20.8, 11.7, 9.4. . HRMS (ESI) calcd for C68H60N3O3S4 (M+H+): 1094.3518, found: 1094.3506.
Example 2:
this example is substantially the same as example 1, with the main differences:
synthesis of a compound of formula (3):
a50 mL three-necked round-bottomed flask was charged with the compound of formula (1) (2 mmol, 932 mg), the compound of formula (2) (3 mmol, 1210 mg), tetrakistriphenylphosphine palladium (0.1 mmol, 116 mg), and 15 mL of toluene in this order under protection of argon; stirring the mixed solution, heating to 110 ℃, reacting for 12 hours, cooling to room temperature, adding water and dichloromethane for extraction, washing an organic phase for 3 times, drying with anhydrous magnesium sulfate, and distilling under reduced pressure to remove the solvent; the crude product was purified by column chromatography (eluent: petroleum ether/dichloromethane = 25/1-1/1) to give 1.25 g of the compound of formula (3) as a dark yellow solid with a yield of 79%.
Synthesis of a compound of formula (4):
under the protection of argon, a compound (790 mg, 1 mmol) of the formula (3), bromomethoxytriphenylamine (766 mg, 2 mmol), potassium carbonate (207 mg, 1.5 mmol), palladium acetate (23 mg, 0.1 mmol), tris (o-methylphenyl) phosphorus (61 mg, 0.2 mmol), pivalic acid (31 mg, 0.3 mmol) and anhydrous N, N-dimethylformamide (5 mL) are sequentially added into a dried Schlenk tube, and the reaction solution is heated to 150 ℃ and continuously stirred for reaction for 30 hours; cooling to room temperature, adding water for quenching, extracting by dichloromethane, washing an organic phase for three times, drying by anhydrous magnesium sulfate, and distilling under reduced pressure to remove the solvent; and (3) purifying the crude product by column chromatography (eluent: petroleum ether/dichloromethane = 15/1-1/1) to obtain 428 mg of the hole transport material (4) as an orange solid with the yield of 39.2%.
Test example: characterization of the hole-transporting material (4):
1. photophysical and electrochemical testing of hole transport materials (4)
The results, as measured by uv-vis absorption and fluorescence emission spectroscopy (fig. 1) and cyclic voltammogram (fig. 2), show: the energy levels of the HOMO (-5.26 eV) and the LUMO (-2.79 eV) of the hole transport material (4) are obviously higher than the energy levels of the halogen-mixed perovskite (HOMO = -5.6 eV and LUMO = -3.9 eV), so that the efficient separation and transmission of holes can be effectively ensured, the transition of electrons from the perovskite layer to the hole transport layer can be effectively blocked, and the occurrence of the interface electron recombination phenomenon can be inhibited.
2. Steady-State fluorescence test of hole transport Material (4)
To better understand the hole transport interaction between the hole layer and the Perovskite layer interface, a sample of ITO/Perovskite/HTM was prepared to study the interface behavior and measure the steady state photoluminescence spectrum of the holes (fig. 3). According to the graph obtained by the test, after the perovskite material shows that a layer of hole transport material (4) is coated in a spinning mode, the fluorescence quenching efficiency reaches 94.5%, and the hole transport material is shown to have excellent hole extraction efficiency, so that the battery performance is improved.
3. I-V Curve test of hole transporting Material (4)
The structural schematic diagram of the perovskite solar cell device is shown in fig. 4, and the preparation steps are as follows:
a. placing ITO (indium tin oxide) conductive glass in an ozone environment, irradiating for 30 minutes by ultraviolet, then ultrasonically cleaning for 30 minutes by deionized water/conductive glass cleaning solution (1 time), deionized water (3 times) and absolute ethyl alcohol (1 time) in sequence, and soaking the treated ITO conductive glass in the absolute ethyl alcohol for later use;
b. controlling the conditions to make tin oxide (SnO)2) Preparation of SnO by spin-coating nanoparticle hydrogel dispersion on ITO conductive glass2Electron transport layer, spin-coating program set to: rotating at 1000 rpm for 3 s and 3300 rpm for 20 s, and annealing at 170 deg.C for 1 hr;
c. a mixed solvent of absolute anhydrous N, N-dimethylformamide and dimethyl sulfoxide is added with formamidine iodine (FAI, concentration of 1M), methylamine bromine (MABr, 0.2M) and lead bromide (PbBr)20.22M), lead iodide (PbI)21.1M) and CsI (concentration of 1.5M) to prepare a cesium-containing triple cation perovskite precursor solution, heating to 50 ℃, stirring for 30 minutes, and filtering for later use;
d. depositing the perovskite film on SnO by adopting a two-step method2On a substrate: the perovskite precursor solution was dropped on the substrate, and the substrate was held at 1000 rpm for 10 seconds at an acceleration of 200 rpm/s, and then at 6000 rpm for 20 seconds at an acceleration of 2000 rpm/s. Dripping 110 μ L of anhydrous chlorobenzene at the center of the substrate 6 seconds before the end of the program, immediately transferring the substrate to a heating plate after the end of the spin coating, and heating at 100 ℃ for 40 minutes;
e. 65.6 mg of the hole transport material (4) was dissolved in 1 mL of chlorobenzene, and then 19.73. mu.L of 4-t-butylpyridine (t-BP) and 11.13. mu.L of a lithium bis (trifluoromethanesulfonyl) imide (LiTFSI) acetonitrile solution (516.76 mg LiTFSI/1 mL of acetonitrile) were added thereto to prepare a solution of the hole transport material. Controlling the rotation speed to be 4000 rpm and the time to be 30s, and coating the hole transport material on the perovskite layer in a rotating mode;
f. and depositing gold with the thickness of about 80 nm on the hole transport layer as a counter electrode by a vacuum evaporation method.
The I-V curve of the device with the hole transport material (4) as the hole transport layer of the perovskite solar cell is shown in the attached figure 5, and the result shows that when the hole transport material (4) is used as the hole transport layer of the perovskite solar cell, the short-circuit photocurrent density reaches 22.98 mA cm-2The open-circuit voltage is 1.099V, the filling factor is 0.7923, the Photoelectric Conversion Efficiency (PCE) is as high as 20.01 percent, and the battery performance is obviously superior to that of a Spiro-OMeTAD (PCE: 18.97 percent, figure 6) under the same preparation and test conditions; meanwhile, the hole transport material (4) is simpler in synthesis route and lower in preparation cost compared with Spiro-OMeTAD.
Claims (7)
1. An asymmetric hole transmission material is characterized in that the material takes tetrathiophene pyrrole as a molecular core, and methoxy triphenylamine and indeno [1,2-b]Carbazole is a peripheral modifying group, and the chemical structural formula is as follows:
2. the method of claim 1, comprising the steps of: s1: subjecting the compound of formula (1) and the compound of formula (2) to a Still coupling reaction to produce a compound of formula (3);
s2: carrying out coupling reaction on the compound shown in the formula (3) and bromomethoxytriphenylamine to generate a compound shown in a formula (4), namely an asymmetric hole transport material;
3. the method of claim 2, wherein the asymmetric hole transport material comprises:
in said S1, the compound of formula (1) is subjected to Still coupling reaction with the compound of formula (2) in toluene solvent under the catalysis of palladium tetratriphenylphosphine to generate the compound of formula (3), wherein the amount of each substance is calculated by the amount of substance, the compound of formula (1): a compound of formula (2): palladium tetratriphenylphosphine =1: 1-2: 0.01-0.2; the reaction time is 4-12 h.
4. The method of claim 2, wherein the asymmetric hole transport material comprises:
in the S2, reacting the compound of the formula (3) with bromomethoxytriphenylamine in anhydrous N, N-dimethylformamide under the action of a palladium catalyst, an organophosphorus ligand, an organic acid and a base to obtain a compound of a formula (4), wherein the amount of each substance is calculated by the mass amount, the compound of the formula (3): bromo methoxy triphenylamine: palladium catalyst: organophosphorus ligands: organic acid: alkali =1: 2-5: 0.01-0.2: 0.02-0.5: 0.2-1: 2-4.
5. The method according to claim 4, wherein the asymmetric hole transport material comprises:
in the step S2, the palladium catalyst is one or a mixture of two or more of tris (dibenzylideneacetone) dipalladium, [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium and palladium acetate; the organophosphorus ligand is one or more of tri (o-methylphenyl) phosphorus, tri (m-methylphenyl) phosphorus, tri (p-methylphenyl) phosphorus, tricyclohexylphosphine, n-butyldi (1-adamantyl) phosphine or 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl; the organic acid is one or a mixture of pivalic acid and acetic acid; the alkali is one or more of sodium carbonate, potassium carbonate, sodium tert-butoxide or potassium tert-butoxide.
6. The method of claim 2, wherein the asymmetric hole transport material comprises: the method also comprises a separation and purification step in each step.
7. Use of an asymmetric hole transport material according to claim 1 in a perovskite solar cell.
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Application publication date: 20200515 Assignee: Tianjin Tianmai Technology Co.,Ltd. Assignor: HUAIYIN INSTITUTE OF TECHNOLOGY Contract record no.: X2022980025822 Denomination of invention: An asymmetric hole transport material and its preparation method and application Granted publication date: 20220527 License type: Common License Record date: 20221212 |