CN112266383B - Method for enhancing molecular planarity of non-spiral organic small molecule hole transport material - Google Patents
Method for enhancing molecular planarity of non-spiral organic small molecule hole transport material Download PDFInfo
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- CN112266383B CN112266383B CN202011276005.9A CN202011276005A CN112266383B CN 112266383 B CN112266383 B CN 112266383B CN 202011276005 A CN202011276005 A CN 202011276005A CN 112266383 B CN112266383 B CN 112266383B
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Abstract
The invention discloses a method for enhancing the molecular planarity of a non-spiro organic micromolecule hole transport material, relates to the technical field of photoelectric materials, and aims to introduce short-range intramolecular interaction between adjacent groups in molecules of non-spiro organic micromolecules. The invention reduces the dihedral angle of adjacent groups in molecules and enhances the molecule planarity by introducing short-range intramolecular interaction in the molecules, effectively enhances the pi-pi accumulation among molecules and improves the hole mobility compared with molecules without short-range intramolecular interaction.
Description
Technical Field
The invention relates to the technical field of photoelectric materials, in particular to a method for enhancing the molecular planarity of a non-spiral organic small molecule hole transport material.
Background
In recent years, organic and inorganic perovskite solar cells are revolutionarily developed in the field of photoelectricity, and the maximum Photoelectric Conversion Efficiency (PCE) of a traditional upright device structure exceeds 23.3%. Due to the limited hole transport capabilities of the perovskite layer itself, hole transport materials have become an integral part of Perovskite Solar Cell (PSCs) devices.
Currently, the most commonly used organic small-molecule hole transport material is 2,2,7, 7-tetrakis [ N, N-bis (4-methoxyphenyl) amino ] -9, 9-spirobifluorene (spiro-OMeTAD), which has many synthesis steps, harsh conditions and complex purification process, resulting in high synthesis cost. In addition, in order to ensure the hole mobility, chemical additives are required to be matched, so that the environmental stability of the device is reduced while the manufacturing cost is increased, and the commercialization of the perovskite solar cell is not facilitated. At present, many researches take triphenylamine as a terminal, and non-spiro molecules taking non-spiro groups as cores are taken as substitutes of spiro-OMeTAD, but because groups connected by single bonds cannot realize better conjugation due to steric hindrance effect, most substitutes cannot have the characteristics of excellent performance and cost reduction. Therefore, the development of a method for enhancing the molecular planarity of the organic small-molecule hole transport material is of great significance to the design of novel cheap high-performance hole transport materials.
Disclosure of Invention
Based on the technical problems in the background technology, the invention provides a molecular planarity enhancing method for a non-spiral organic small molecule hole transport material, which effectively enhances pi-pi accumulation among molecules of the organic small molecule hole transport material and improves hole mobility.
The invention provides a method for enhancing the molecular planarity of a non-spiro organic micromolecule hole transport material, which introduces short-range intramolecular interaction between adjacent groups in molecules of the non-spiro organic micromolecules.
Preferably, the short-range intramolecular interaction refers to steric interaction between atoms or groups at a distance of 6 chemical bonds or less along a macromolecular chain.
Preferably, the steric interaction comprises a dipole-dipole interaction or/and a hydrogen bond.
The invention also provides a non-spiro organic micromolecule hole transport material obtained based on the method, and the structural formula of the non-spiro organic micromolecule hole transport material is shown as the formula (I):
formula (I)
Wherein R is1Selected from H, F, Cl, Br, I, CN, Si (CH)3)3、B(OH)2、C1～C40Straight or branched alkyl of (2), C1～C40Straight or branched alkoxy, C1～C40Cycloalkyl radical, C3～C30A heteroaryl group;
X1and X2There is a process intramolecular interaction between them, when X1Is S, X2Is F, or X1Is O, X2Is F, or X1Is NH, X2Selected from H, F;
X3selected from C, N;
X4selected from O, S, NH.
Preferably, said C3～C30The heteroatoms in the heteroaryl group are one or more of O, S, N.
In the invention, the non-spiro organic small molecule hole material obtained by introducing the short-range intramolecular interaction method is not limited to the structure of the formula (I), and can also be other various non-spiro organic small molecule hole materials with different structural general formulas.
The invention also provides a preparation method of the non-spiral organic small molecule hole transport material, which comprises the following steps:
adding a compound shown as a formula (II), 4-boric acid ester-4 ',4' -dimethoxy triphenylamine, alkali liquor and ethanol into a reaction solvent, refluxing under the protection of inert atmosphere and the action of a palladium catalyst to perform Suzuki coupling reaction, cooling to room temperature after the reaction is finished, extracting, passing through a column, and recrystallizing to obtain a non-spiro organic micromolecule hole transport material shown as a formula (I);
formula (II);
wherein R is1Selected from H, F, Cl, Br, I, CN, Si (CH)3)3、B(OH)2、C1～C40Straight or branched alkyl of (2), C1～C40Straight or branched alkoxy, C1～C40Cycloalkyl radical, C3～C30A heteroaryl group;
X1and X2There is a process intramolecular interaction between them, when X1Is S, X2Is F, or X1Is O, X2Is F, or X1Is NH, X2Selected from H, F;
X3selected from C, N;
X4selected from O, S, NH.
Preferably, the reaction solvent is dimethylformamide or tetrahydrofuran; preferably, the palladium catalyst is one or more of palladium acetate, palladium bis (triphenylphosphine) dichloride and tetrakis (triphenylphosphine) palladium; preferably, the alkali liquor is an aqueous solution of one of potassium carbonate, potassium phosphate, potassium tert-butoxide, sodium carbonate, sodium tert-butoxide and sodium hydroxide, and the concentration of the alkali liquor is preferably 1-2 mol/L.
Preferably, the mass ratio of the compound of formula (II), 4-boronate-4 ',4' -dimethoxytriphenylamine, tetrakis (triphenylphosphine) palladium and base is 1: 2-3: 0.05-0.1: 2-20.
Preferably, the refluxing temperature of the Suzuki coupling reaction is 70-130 ℃, and the refluxing time is 24-36 hours.
In the present invention, the inert atmosphere is nitrogen or argon.
The stationary phase used by the column is silica gel, and the mobile phase used is one or more of petroleum ether, dichloromethane, n-hexane and ethyl acetate.
And the recrystallization adopts one or more of dichloromethane, normal hexane and toluene as a solvent for recrystallization.
The invention also provides a perovskite solar cell which comprises a substrate, and a cathode layer, an electron transport layer, a light absorption layer, a hole transport layer and an anode layer which are sequentially arranged on the substrate, wherein the hole transport layer at least comprises the non-spiro organic micromolecule hole transport material obtained by the method for introducing the short-range intramolecular interaction or the non-spiro organic micromolecule hole transport material with the structure shown in the formula (I) obtained by the method or the preparation method.
Has the advantages that: the invention provides a method for enhancing the molecular planarity of a non-spiro organic micromolecule hole transport material, which introduces short-range intramolecular interaction between adjacent groups in molecules of the non-spiro organic micromolecules, reduces the dihedral angle of the adjacent groups in the molecules, enhances the molecular planarity, effectively enhances the pi-pi accumulation between the molecules and improves the hole mobility compared with molecules without short-range intramolecular interaction.
Drawings
FIG. 1 shows the molecular structures and their optimal molecular conformations of compound M2 and compound M0 in the examples of the present invention.
FIG. 2 is a SCLC curve of compound M2 and compound M0 in an example of the present invention.
FIG. 3 shows perovskite solar cell devices prepared by using compound M2 and compound M0 as hole transport materials in the embodiment of the invention.
FIG. 4 is a J-V curve of perovskite solar cell devices prepared by using compound M2 and compound M0 as hole transport materials in an example of the present invention.
Detailed Description
The technical means of the present invention will be described in detail below with reference to specific examples.
Example 1
(1) Synthesis of compound M0:
the method comprises the following specific steps:
in a 50mL round-bottom flask, compound 1(458mg, 1mmol), 4-boronate-4 ',4' -dimethoxytriphenylamine (1.08g, 2.5mmol), an aqueous solution of potassium carbonate (4M, 4mL), Pd (PPh)3)4(57mg, 0.05mmol), anhydrous DMF (20mL) and anhydrous ethanol (4 mL). The reaction solution was stirred at 120 ℃ under nitrogen for 24 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, extracted with ethyl acetate and washed with saturated brine. The organic phase was dried over anhydrous magnesium sulfate and concentrated by rotary evaporation, the crude product was isolated by column chromatography using petroleum ether/dichloromethane (v/v. 5/1) as eluent and reacted to yield 589mg of the product as a purple solid in 65% yield. 1H NMR (300MHz, CDCl)3)δ8.10-8.09(d，2H)，7.84(s，2H)，7.51-7.48(d，4H)，7.28-7.27(d，2H)，7.10-7.06(m，8H)，6.95-6.92(m，4H)，6.86-6.82(m，8H)，3.81(s，12H)。
(2) Synthesis of Compound M2
The method comprises the following specific steps:
in a 50mL round-bottom flask, compound 2(494mg, 1mmol), 4-boronate-4 ',4' -dimethoxytriphenylamine (1.08g, 2.5mmol), an aqueous solution of potassium carbonate (4M, 4mL), Pd (PPh)3)4(57mg, 0.05mmol), anhydrous DMSO (20mL), and anhydrous ethanol (4 mL). The reaction solution was stirred at 120 ℃ under nitrogen for 24 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, extracted with ethyl acetate and washed with saturated brine. The organic phase is dried over anhydrous magnesium sulfate and concentrated by rotary evaporation, whereuponThe crude product was isolated by column chromatography using petroleum ether/dichloromethane (v/v. 5/1) as eluent and reacted to give 632mg of a purple solid product in 67% yield. 1H NMR (300MHz, CDCl)3)δ8.54-8.52(d，1H)，8.23-8.22(d，1H)，7.54-7.48(t，4H)，7.32-7.30(d，2H)，7.13-7.09(m，8H)，6.97-6.93(m，4H)，6.90-6.88(d，8H)，3.83(s，12H)。
The thiophene sulfur and fluorine substituents in the molecule of the synthesized compound M2 have F.S short-range intramolecular interaction, and M0 has no short-range intramolecular interaction.
The optimal molecular conformations of M0 and M2 are obtained by DFT theoretical calculation, as shown in figure 1, the dihedral angle (1.0-1.1 ℃) between the thiophene bridge and the benzothiadiazole core in M2 is obviously lower than the dihedral angle between the thiophene bridge and the benzothiadiazole core in M0.
Example 2
Compound M2 and compound M0 synthesized in example 1 were used to prepare single cavitator FTO/PEDOT: PSS/HTM/Au, respectively, and a current-confined space method was used to obtain J shown in FIG. 21/2-V curve (SCLC) estimating hole mobility. As a result, the hole mobility of M2 was calculated to be 1.33X 10-6cm2 V-1s-1M0 hole mobility 8.92X 10-7cm2 V-1s-1. It can be seen that the void mobility of compound M2 is significantly higher than that of compound M0.
Example 3
The compound M2 synthesized in example 1 and the compound M0 thereof are applied to an organic-inorganic perovskite solar cell as an undoped hole transport material, and the structure is as follows: FTO/ETM/m-TiO2/MAPbI3(ii)/HTM/Au, as shown in FIG. 3; the compound M2 can be used as a hole transport material for, but is not limited to, such perovskite solar cell structures. The perovskite solar cell preparation process comprises the following steps: first, FTO conductive glass (15. omega./square, thickness 2.3mm) was cut into 1.5cm by 2cm small pieces, which were then etched in accordance with the electrode pattern using zinc powder and 2M hydrochloric acid. And after etching, ultrasonically cleaning the glass for ten minutes by using acetone and ethanol respectively, blow-drying by using clean compressed air, and then annealing for 30min at 510 ℃. 7mL of isopropanol and 0.6mL of tetraisopropyl titanate were addedThe ester and 0.4mL of acetic acid acetone are uniformly mixed, then the mixture is sprayed on an FTO glass substrate in a heating state at 450 ℃ by taking nitrogen as carrier gas, and the FTO glass substrate is naturally cooled after being heated for 20 min. Adding TiO into the mixture2And mixing the slurry (Dyesol 30NR-T) and the ultra-dry ethanol according to a mass ratio of 1: 5.5, and then carrying out ultrasonic treatment and stirring to uniformly disperse the mixture. The slurry was spin coated onto the dense substrate layer at 4000rpm and then sintered at 510 ℃ for 30 min. 0.795g of PbI2，0.269g CH3NH3I was dissolved in 1.275mL DMSO and 0.225mL DMF and stirred at 70 ℃ for two hours to give MAPbI3Precursor solution, filtering the prepared precursor solution with a 0.45 mu m polytetrafluoroethylene filter, and then dripping 60 mu L of precursor solution to TiO2On the substrate, spin coating was divided into two processes, the first process being 1000rpm spin coating for 10s, followed by a process being 4000rpm spin coating for 30 s. 150 μ L of chlorobenzene was added dropwise to the basal layer 15s before the end of the second process. After the spin coating was completed, the film was annealed at 100 ℃ for 1 hour. 20mg of compound M0 and compound M2 were dissolved in chlorobenzene, respectively, and spin-coated onto the naturally cooled perovskite thin film at 4000rpm for 30s to obtain a Hole Transport (HTM) layer. And finally, evaporating and plating a 60nm Au electrode on the hole transport layer by using a vacuum evaporation plating machine to obtain the perovskite solar cell device shown in the figure 3.
Example 4
The intensity of the light source was measured to be AM 1.5G (100mW cm) using a xenon lamp solar simulator-2) And carrying out photovoltaic performance test on the prepared perovskite solar cell. The cell light state I-V curve is tested by using a 3A level standard light source (94043A, Newport company, USA) and a digital source table (2420, Keithley company, USA), and test engineering and data output are generated by using Testpoint software. The corresponding results are shown in fig. 4. The results show that the perovskite solar cell device using the compound M2 as a hole transport material shows higher open-circuit voltage, current density, filling factor and photoelectric conversion efficiency than the compound M0. The M2 with the short-range intramolecular interaction is shown to have better photovoltaic performance and show good application prospect.
In conclusion, the molecular DFT optimal molecular conformation, the device performance of the material and the hole mobility test show that the organic micromolecules have better planarity, hole mobility and device efficiency based on the introduction of short-range intramolecular interaction between adjacent groups in the molecules of the non-spiral organic micromolecules.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention.
Claims (5)
1. A non-spiro organic small molecule hole transport material is characterized in that the structural formula of the non-spiro organic small molecule hole transport material is shown as the formula (I):
formula (I)
Wherein R is1Is H; x1And X2There is a process intramolecular interaction between them, X1Is S, X2Is F; x3Is N; x4Is S.
2. The preparation method of the non-spiro organic micromolecule hole transport material according to claim 1 is characterized in that a compound shown in a formula (II), 4-borate-4 ',4' -dimethoxy triphenylamine, alkali liquor and ethanol are added into a reaction solvent, reflux is carried out under the protection of inert atmosphere and the action of a palladium catalyst to carry out Suzuki coupling reaction, after the reaction is finished, the mixture is cooled to room temperature, extracted, passed through a column and recrystallized to obtain the non-spiro organic micromolecule hole transport material shown in the formula (I);
formula (II)
The R is1Selected from H, X1And X2There is a process intramolecular interaction between them, X1Is S, X2Is F; x3Is selected from N; x4Is selected from S;
the reaction solvent is dimethylformamide or tetrahydrofuran; the palladium catalyst is one or more of palladium acetate, bis (triphenylphosphine) palladium dichloride and tetra (triphenylphosphine) palladium; the alkali liquor is an aqueous solution of one of potassium carbonate, potassium phosphate, potassium tert-butoxide, sodium carbonate, sodium tert-butoxide and sodium hydroxide, and the concentration of the alkali liquor is 1-2 mol/L.
3. The method for preparing a non-spiro organic small molecule hole transport material according to claim 2, wherein the amount ratio of the compound of formula (ii), 4-boronate-4 ',4' -dimethoxytriphenylamine, tetrakis (triphenylphosphine) palladium and base is 1: 2-3: 0.05-0.1: 2-20.
4. The preparation method of the non-spiro organic small molecule hole transport material according to claim 2, wherein the refluxing temperature of the suzuki coupling reaction is 70-130 ℃ and the refluxing time is 24-36 hours.
5. A perovskite solar cell is characterized by comprising a substrate, and a cathode layer, an electron transport layer, a light absorption layer, a hole transport layer and an anode layer which are sequentially arranged on the substrate, wherein the hole transport layer at least comprises a non-spiro organic micromolecule hole transport material according to any one of claims 1 to 4.
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