CN113150011A - Diazosulfide dipyrrolodithiophene-based interface material and preparation method and application thereof - Google Patents
Diazosulfide dipyrrolodithiophene-based interface material and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a diazosulfide dipyrrolodithiophene interface material and a preparation method and application thereof. The structural formula of the compound is shown as the formula I: in the formula I, R1Is C3～C12Alkyl chain of (A), R2Is methoxy or methylthio. The preparation method of the compound shown in the formula I comprises the following steps: dissolving brominated DTPBT substituted by different side chains and boric acid derivatives in an organic solvent, sequentially adding alkali and a palladium catalyst, and carrying out a Suzuki reaction under the nitrogen condition to obtain the compound shown in the formula I. The compound shown in the formula I is applied to preparing an interface layer in a perovskite solar cell. The compound shown in the formula I has better solubility in common solvents for preparing perovskite solar cells; has good hole transport performanceAnd electron blocking properties, which facilitate efficient selective transport of holes; the method can passivate the surface defects of the perovskite, inhibit the generation of impurity phases of the perovskite, and is beneficial to improving the efficiency and stability of the perovskite solar cell.
Description
Technical Field
The invention belongs to the field of photoelectricity, and relates to a diazosulfide dipyrrolo dithienyl interface material, a preparation method and an application thereof, in particular to a diazosulfide dipyrrolo dithienyl interface material, a preparation method thereof and an application thereof in a perovskite solar cell.
Background
The perovskite has the advantages of high light absorption coefficient, wide light absorption range, high carrier mobility, long diffusion length and the like. The band gap can be tuned by varying the cations and/or halides, and the unique optoelectronic properties of perovskite materials have attracted attention of researchers worldwide. The highest authentication efficiency of the current perovskite solar cell reaches 25.2%, the perovskite prepared by a solution method can leave defects on the surface of the perovskite, and in addition, hygroscopic additives which must be introduced in the use of a common hole transport material, namely Spiro-OMeTAD, also limit the improvement of the efficiency and the stability of the perovskite solar cell. Therefore, the synthesis of the interface material with defect passivation and hole transmission capability has important significance. In order to further improve the efficiency and stability of perovskite solar cells, it is necessary to design an interface material to passivate the surface defects of the perovskite.
Disclosure of Invention
The invention aims to provide a benzothiadiazolobipyrrolodithienyl interface material, and a preparation method and application thereof.
According to the invention, benzothiadiazolobipyrrolodithiophene (DTPBT) with different substituents is used as a raw material, and a DTPBT-based interface material is designed and prepared. The experimental result shows that the compounds have proper energy level distribution and good hole transmission capability; the perovskite solar cell with the amorphous silicon oxide as the interface layer is applied to perovskite solar cells, surface defects of perovskite can be passivated, and good photoelectric conversion efficiency and long-term stability are further achieved, so that the perovskite solar cell with the amorphous silicon oxide as the interface layer has a good application prospect.
The invention provides a compound, which has a structural formula shown in a formula I:
in the formula I, R1Is C3～C12Alkyl chain of (A), R2Is methoxy or methylthio.
In the compound represented by the formula I, R is1Is C3～C6Alkyl chain of (2).
The most preferred compound shown in the formula I is used as a DTPBT-based interface material and has a structure shown in the formula II:
in the invention, the compound shown in the formula I is used as a benzothiadiazoledipyrrolodithiophene (DTPBT) base interface material.
The invention also provides a preparation method of the compound shown in the formula I, which comprises the following steps: dissolving brominated DTPBT substituted by different side chains shown in a formula III and boric acid derivatives shown in a formula IV in an organic solvent, sequentially adding alkali and a palladium catalyst, and carrying out a Suzuki reaction under the nitrogen condition to obtain a compound shown in a formula I;
in the preparation method, the molar ratio of the brominated DTPBT with different side chain substitutions in the formula III to the boric acid derivative in the formula IV to the alkali to the palladium catalyst can be 1: 2-4: 4-20: 0.01-0.10, and specifically can be 1:3:5: 0.1.
In the preparation method, the temperature of the Suzuki reaction can be 80-140 ℃, and the time can be 12-48 h; the Suzuki reaction can be carried out by adopting solvent reflux.
In the above preparation method, the base is at least one of sodium tert-butoxide, potassium carbonate, sodium carbonate, cesium carbonate, potassium phosphate, and sodium hydroxide.
In the above preparation method, the palladium catalyst is at least one of palladium acetate, palladium bis (triphenylphosphine) dichloride, tetrakis (triphenylphosphine) palladium and palladium/carbon.
In the above preparation method, the organic solvent is at least one of toluene, xylene, tetrahydrofuran, dioxane, dimethylformamide, ethanol and dimethyl sulfoxide.
In the invention, the post-treatment of the preparation method adopts a method known in the art for treatment, and specifically can be column chromatography separation and purification.
The invention relates to a specific preparation method of a compound shown in a formula I, which specifically takes a DTPBT-based interface material with a structure shown in a formula II as an example, and comprises the following specific steps:
1) reacting the compound 1 with n-butyl bromide under the catalysis of alkali to obtain a compound 2;
2) reacting the compound 2 with NBS in a mixed solution of chloroform and acetic acid to obtain a compound 3;
3) and (3) carrying out Suzuki reaction on the compound 3 and [4- [ bis (4-methoxyphenyl) amino ] phenyl ] boric acid under the catalysis of Pd to obtain a final product II.
The compound shown in the formula I is applied to preparing an interface layer in a perovskite solar cell.
The invention further provides a perovskite solar cell which sequentially comprises a transparent substrate, an electron transport layer, a perovskite layer, an interface layer, a hole transport layer and a metal electrode from bottom to top;
the interface layer is prepared by the compound shown in the formula I.
The preparation method of the perovskite solar cell comprises the following steps:
(1) preparing dense SnO layer on transparent conductive substrate ITO by adopting spin coating technology2And forming an electron transport layer.
(2) And (3) spinning and coating the perovskite precursor solution on the electron transport layer, and growing a high-quality perovskite structure light absorption layer thin film after annealing.
(3) An interface layer (the compound shown in the formula I, DTPBT-based interface material) is prepared on the light absorption layer by a spin coating method.
(4) A hole transport layer (doped type Spiro-OMeTAD) was prepared on the interface layer by spin coating.
(5) And preparing a top electrode Au on the hole transport layer by vacuum thermal evaporation.
In the step (1), the transparent conductive substrate is ITO glass, and the square resistance of the substrate is about 10 omega/sq; the spin-coated precursor solution is prepared from SnO2An aqueous solution.
The spin-coating speed is 3000-4000rpm, the spin-coating time can be 30-40 s, the sintering temperature is 100-200 ℃, the sintering time can be 10-40 min, and the preferable operation can be 30s at 3000rpm and 30 min at 150 ℃.
In the step (2), the perovskite precursor solution is PbI2And CH3NH3I、HC(NH2)2I、CH3NH3And the perovskite precursor is formed by randomly combining Cl. The solvent can be gamma-butyrolactone (GBL), dimethyl sulfoxide (DMSO) or Dimethylformamide (DMF), or a mixed solution in a certain proportion.
The precursor solution is firstly formed into a film on a substrate by a spin coating method, and meanwhile, a certain high-concentration solvent atmosphere is ensured in a spin coating chamber. Wherein the rotating speed can be 3000 plus 5000rpm, and the film throwing time is 10-45 s; preferably 3000rpm, for 30 s.
The annealing temperature can be 80-120 ℃, and the annealing time is 10-30 minutes; preferably, the operation is carried out at 150 ℃ for 10 minutes.
In the step (3), the interface layer raw material is a DTPBT-based interface material. The film is prepared by a spin coating method, the rotating speed can be 3000-5000rpm, and the spin coating time is 20-40 s. Preferably 4000rpm, for 30 s.
And (4) adopting a Spiro-OMeTAD as a raw material of the hole transfer layer in the step (4). Preparing a film by a spin coating method, wherein the rotating speed can be 2000-5000 rpm, and the spin coating time can be 30-45 s; preferably 3000rpm, for 30 s.
The invention has the following advantages:
(1) the compound shown in the formula I, which is prepared by the invention, has better solubility in common solvents such as dimethyl sulfoxide, chlorobenzene, toluene, chloroform and the like for preparing perovskite solar cells when being used as a DTPBT-based interface material.
(2) The DTPBT-based interface material prepared by the invention has good hole transport performance and electron blocking performance, and is beneficial to effective selective transport of holes.
(3) The DTPBT-based interface material prepared by the invention can realize the passivation of perovskite surface defects, inhibit the generation of impurity phases thereof and is beneficial to improving the efficiency and stability of perovskite solar cells.
Drawings
FIG. 1 is an ultraviolet absorption spectrum of example 1 of the present invention;
FIG. 2 is a steady state spectrum of perovskite coated in example 1 of the present invention;
FIG. 3 is an XPS spectrum applied to perovskite in example 1 of the present invention;
FIG. 4 is a graph of current versus voltage for a perovskite solar cell prepared in example 1 of the present invention.
Detailed Description
The experimental procedures used in the following examples are all conventional procedures unless otherwise specified.
Materials, reagents and the like used in the following examples are commercially available unless otherwise specified.
The preferred embodiments of the present invention will now be described in detail with reference to the accompanying drawings, which form a part hereof, and which together with the embodiments of the invention serve to explain the principles of the invention.
Example 1 synthesis of a DTPBT-based interface material having a structural unit of formula ii.
The DTPBT-based interface material with the chemical structural formula shown as the formula II comprises the following synthetic route:
synthesis of Compound (1) is described in Cheng Y J, Chen C H, Ho Y J, et al, Thieno [3, 2-b ] pyrorolo Donor Fused with benzothiazadiazolo, Benzoselenadiazolo and Quinoxalino Acceptors: Synthesis, Characterisation, and Molecular Properties [ J ] Organic Letters,2011,13(20):5484-7.
Synthesis of Compound (2):
potassium tert-butoxide (990mg,8.82mmol), 1-bromobutane (0.93ml,8.82mmol) and compound 1(480mg,1.47mmol) were added to 15ml of tetrahydrofuran and stirred under nitrogen protection at 90 ℃ under reflux for 24 h. After the reaction, the mixture was extracted with dichloromethane and water, and the collected organic phase was extracted with anhydrous MgSO4Drying and filtering. After removal of the solvent under reduced pressure, the crude product was purified by silica gel column chromatography (eluent: petroleum ether/dichloromethane, 1/1) and recrystallized from dichloromethane and n-hexane to give 313mg of a yellow solid in a yield of 48%.
Synthesis of Compound (3):
compound 2(300mg,0.68mmol) was added to a mixed solution of chloroform (10 mL)/acetic acid (10 mL). The reaction flask was wrapped with aluminum foil and placed in an ice bath, n-bromosuccinamide (267.8mg,1.50mmol) was added in portions, stirred at 0 ℃ for 1h, then warmed to 35 ℃ and stirred for 1 h. The reaction was quenched with water (80mL) and extracted with dichloromethane, and the collected organic phase was washed with anhydrous MgSO4Drying and filtering. After removal of the solvent under reduced pressure, the crude product was purified by silica gel column chromatography (eluent: petroleum ether/dichloromethane, 4/1) and the product was recrystallized from dichloromethane and n-hexane to give 186mg of an orange-yellow solid in a yield of 46%.
Synthesis of an interface material having the structure of formula II:
compound 3(80mg, 0.13mmol), [4- [ bis (4-methoxyphenyl) amino]Phenyl radical]Boric acid (117.0mg,0.34mmol), Pd (PPh)3)4(12.1mg,0.01mmol) and K2CO3(2.6mL,2M) was added to 15mL tetrahydrofuran and stirred at 90 deg.C under nitrogen at reflux for 24 h. After the reaction, the mixture was extracted with dichloromethane and water, and the collected organic phase was extracted with anhydrous MgSO4Drying and filtering. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate, 5/1), the product was recrystallized from dichloromethane and n-hexane,56mg of a red solid are obtained in 42% yield.
The structure was confirmed as follows:1H NMR(400MHz,CDCl3):δ7.52(d,J＝8Hz,4H),7.27(s,2H),7.09(d,J＝8Hz,8H),6.96(d,J＝8Hz,4H),6.85(d,J＝8Hz,8H),4.52(t,J＝8Hz,4H),3.82(s,12H),1.86-1.79(m，4H)，1.19-1.10(m，4H)，0.83(t，J＝8Hz，6H).MALDI-TOF(m/z):calcd for C62H56N6O4S3 1044.35,found 1044.76.
in conclusion, the invention provides a DTPBT-based interface material, and preparation and application thereof. The interface material has a DTPBT and triarylamine structural unit, and is modified by two n-butyl side chains. It has good solubility in solvents.
The compound is applied to perovskite solar cells, hole transmission and defect passivation can be realized, and photoelectric conversion efficiency and stability are improved, so that the compound has wide application prospects in the fields of perovskite cells and the like. The specific experiment is as follows:
the perovskite solar cell device is prepared by the following specific steps:
(1) and ultrasonically cleaning the ITO substrate by isopropanol, blow-drying the ITO substrate by nitrogen, and carrying out ultraviolet treatment for 20 minutes to improve the surface wettability.
(2) SnO2The solution was then spin coated onto the UV treated ITO substrate at 4000r/s for 30 s. And then annealed at 150 c for 30 minutes to form an electron transport layer. The UV treatment was again carried out for 20 minutes.
(3) 671.5mg of lead iodide (PbI) were weighed out2) Dissolved in 1ml of a mixed solvent of N, N-Dimethylformamide (DMF) and dimethyl sulfoxide (DMSO) (volume ratio of 9: 1). PbI2Coating the powder on SnO at 1500r/s in a spinning way2The layer was kept for 30 seconds, transferred to a 70 ℃ hot stage and heated for 1 minute and then cooled naturally.
(4) 90mg of formamidine hydroiodide (FAI),6.39mg of Methyl Amine Iodide (MAI) and 9mg of methyl amine chloride (MACl) were weighed out and dissolved together in 1ml of isopropanol and filtered, and spin-coated onto the naturally cooled PbI at 2000r/s2The layer, after a duration of 30s, was transferred to air and annealed at 150 ℃ for 15 minutes.
(5) The molecule of formula II (also known as BDAD) was dissolved in chlorobenzene to make a 2mg/ml solution which was spin coated at 5000r/s on the annealed perovskite layer for 30 s.
(6) After weighing 72.3mg of Spiro-OMeTAD in 1ml of chlorobenzene, 35. mu.l of LiTFSI (0.91M in acetonitrile as solvent) and 30. mu. l t-BP were added and spin-coated at 3000r/s on the layer of perovskite modified with the molecule of formula II for 30 s.
(7) Finally, gold of about 70nm is deposited on the top of the device as an electrode by a vacuum evaporation method.
The method and results of the experiment of FIG. 2 illustrate that:
the experimental method comprises the following steps: and (3) directly finishing the steps (3) and (4) in the preparation of the device on the ITO substrate to obtain a pure Perovskite (PVK) film, and then performing the step (5) to obtain the PVK/BDAD film. And photoluminescence spectra (PL) of two different films were tested.
The results show that: the BDAD (i.e. the compound shown in the formula II) coated perovskite thin film shows strong fluorescence quenching compared with a pure perovskite thin film, which indicates that the BDAD (i.e. the compound shown in the formula II) has stronger hole extraction capability.
The experimental method and results of fig. 3 illustrate that:
the experimental method comprises the following steps: and (3) directly finishing the steps (3) and (4) in the preparation of the device on the ITO substrate to obtain a pure Perovskite (PVK) film, and then performing the step (5) to obtain the PVK/BDAD film. And two different films were tested for X-ray photoelectron spectroscopy (XPS).
The results show that: the perovskite thin film without BDAD modification has two strong peaks at 143.3 eV and 138.5eV, and the two peaks are respectively assigned to Pb 2+4f of5/2And 4f7/2Two signals. In addition, two weak peaks were observed at 141.3 and 136.7eV, which is attributed to Pb0Caused by a defect. However, after BDAD modification, 4f5/2And 4f7/2Both signals move to 143.2 and 138.3eV in the low binding energy direction, while Pb is present0The signal of (2) disappears completely. These changes indicate that there is a clear interaction between BDAD and perovskite that can achieve defect passivation.
The method and results of the experiment of FIG. 4 illustrate that:
experiment ofThe method comprises the following steps: based on the device technology, a series of ITO/SnO are prepared2Planar perovskite solar cell device with basic structure of/PVK/BDAD/spiral-OMeTAD/Au, and performing photovoltaic test to obtain device performance index
The results show that:
BDAD modified device short circuit current (J)sc) Reaches 24.74mA cm-2，(Voc) 1.17V, (FF) 78.34%, and energy conversion efficiency (PCE) 22.76%, 15.3% higher than PCE (19.73%) of the control group device.
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 changes or substitutions that can be easily conceived by those skilled in the art within the technical scope of the present invention are included in the scope of the present invention.
Claims (10)
1. A compound having a structural formula shown in formula I:
in the formula I, R1Is C3～C12Alkyl chain of (A), R2Is methoxy or methylthio.
2. The compound of claim 1, wherein: in the formula I, R is1Is C3～C6Alkyl chain of (2).
3. A process for the preparation of a compound of formula I according to claim 1 or 2, comprising the steps of: dissolving brominated DTPBT substituted by different side chains shown in a formula III and boric acid derivatives shown in a formula IV in an organic solvent, sequentially adding alkali and a palladium catalyst, and carrying out a Suzuki reaction under the nitrogen condition to obtain a compound shown in a formula I;
4. the production method according to claim 3, characterized in that: the molar ratio of the brominated DTPBT with different side chains substituted in the formula III to the boric acid derivative shown in the formula IV to the alkali to the palladium catalyst is 1: 2-4: 4-20: 0.01-0.10.
5. The production method according to claim 3 or 4, characterized in that: the temperature of the Suzuki reaction is 80-140 ℃, and the time is 12-48 h.
6. The production method according to any one of claims 3 to 5, characterized in that: the alkali is at least one of sodium tert-butoxide, potassium carbonate, sodium carbonate, cesium carbonate, potassium phosphate and sodium hydroxide.
7. The production method according to any one of claims 3 to 6, characterized in that: the palladium catalyst is at least one of palladium acetate, palladium bis (triphenylphosphine) dichloride, tetrakis (triphenylphosphine) palladium and palladium/carbon.
8. The production method according to any one of claims 3 to 7, characterized in that: the organic solvent is at least one of toluene, xylene, tetrahydrofuran, dioxane, dimethylformamide, ethanol and dimethyl sulfoxide.
9. Use of a compound of formula I according to claim 1 or 2 for the preparation of an interfacial layer in a perovskite solar cell.
10. A perovskite solar cell, characterized in that: the perovskite solar cell comprises a transparent substrate, an electron transport layer, a perovskite layer, an interface layer, a hole transport layer and a metal electrode from bottom to top in sequence;
the interfacial layer is made from a compound of formula I according to claim 1 or 2.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105705610A (en) * | 2013-08-23 | 2016-06-22 | 巴斯夫欧洲公司 | Compounds with terminal heteroarylcyanovinylene groups and their use in organic solar cells |
| CN109467561A (en) * | 2018-11-19 | 2019-03-15 | 广东工业大学 | A kind of double donor hole mobile materials containing phenothiazine structure and preparation method thereof and perovskite solar battery |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105705610A (en) * | 2013-08-23 | 2016-06-22 | 巴斯夫欧洲公司 | Compounds with terminal heteroarylcyanovinylene groups and their use in organic solar cells |
| CN109467561A (en) * | 2018-11-19 | 2019-03-15 | 广东工业大学 | A kind of double donor hole mobile materials containing phenothiazine structure and preparation method thereof and perovskite solar battery |
Non-Patent Citations (3)
| Title |
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| XIAOXIA YE ET AL.: "Effect of the acceptor and alkyl length in benzotriazole-based donoracceptor-donor type hole transport materials on the photovoltaic performance of PSCs", 《 DYES AND PIGMENTS》 * |
| YEN-JU CHENG ET AL.: "Thieno[3,2-b]pyrrolo Donor Fused with Benzothiadiazolo, Benzoselenadiazolo and Quinoxalino Acceptors: Synthesis, Characterization, and Molecular Properties", 《ORGANIC LETTERS》 * |
| YU-DUAN WANG ET AL.: "Defect Passivation by a D−A−D Type Hole-Transporting Interfacial Layer for Efficient and Stable Perovskite Solar Cells", 《ACS ENERGY LETT.》 * |
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