CN112194573B - Six-arm star-shaped material taking truxene as core and application thereof in perovskite solar cell - Google Patents
Six-arm star-shaped material taking truxene as core and application thereof in perovskite solar cell Download PDFInfo
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- CN112194573B CN112194573B CN202011238613.0A CN202011238613A CN112194573B CN 112194573 B CN112194573 B CN 112194573B CN 202011238613 A CN202011238613 A CN 202011238613A CN 112194573 B CN112194573 B CN 112194573B
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/21—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing rings other than six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/92—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the nitrogen atom of at least one of the amino groups being further bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/10—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising heterojunctions between organic semiconductors and inorganic semiconductors
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- C07C2603/54—Ortho- or ortho- and peri-condensed systems containing more than five condensed rings
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- Photovoltaic Devices (AREA)
Abstract
The invention discloses a six-arm star-shaped material taking indene trimer as a core, which has a structure shown in a formula I, wherein R is selected from H, C1-C50 straight-chain alkyl or branched-chain alkyl; ar is at least one of benzene, anisole, diphenylamine, dimethoxydiphenylamine, triphenylamine, trimethoxytriphenylamine, carbazole, 3, 6-bis (dimethoxydiphenylamine) carbazole, 3, 6-bis (trimethoxytriphenylamine) carbazole or derivatives of the above compounds. The material of the invention is of a six-arm star structure with the truxene as a core, has good planarity and high hole mobility, and can be applied to organic photoelectric devices as a hole transport layer so as to improve the photoelectric conversion efficiency of perovskite cell devices and remarkably improve the performance of the devices.
Description
Technical Field
The invention relates to the technical field of organic photoelectricity, in particular to a six-arm star-shaped material taking truxene as a core and application thereof in a perovskite solar cell.
Background
According to 2016 research front, 2017 research front, 2018 research front and 2019 research front in chemical materials, 2019 research front, which are jointly issued by scientific and technological strategy consulting research institute, chinese academy of sciences and Kerui Weian (Clarivate Analytics), perovskite solar cells are always in ten hot spots of chemistry and materials Science, particularly, in 2017, a novel organic hole transport material in the perovskite cells is arranged at the second place of the hot spot front of the year, and the photoelectric conversion efficiency of the perovskite solar cells is 25.17% of broken records through extensive and deep research of domestic and foreign research institutions (Science, 2020,370, 108-112). In the process of supporting the record, the hole transport material plays a role of lifting, the hole transport layer requires that the hole mobility of the material is high, and then the HOMO energy level matched with the valence band of the perovskite material is needed, and good stability and film forming property are needed again, so that the effective injection and transmission of holes at each interface are ensured.
The organic hole transport material improves Schottky contact between an electrode and perovskite, promotes electrons and holes to be separated at a functional layer interface, reduces charge recombination, has materials which can be selected in a large range and are different from inorganic hole transport materials, can adjust energy level matching and surface properties through flexible design, and is relatively widely researched. Organic hole transport materials used in the perovskite field are most classically PTAA and Spiro-OMeTAD, and other materials are generally variants of both materials. The Seok topic group can obtain 22.1% of certified photoelectric conversion efficiency by taking PTAA as an organic hole transport layer, and the photoelectric conversion efficiency is 1cm 2 An area of the cell still achieves an efficiency of 19.7% (Science, 2017,356, 1376-1379).The subject group obtained 21.02% of certification efficiency as early as 2016 with a Spiro-OMeTAD organic hole transport layer, laboratory efficiency as high as 21.6%, and high reproducibility (Nature Energy,2016,1, 16142); in 2020, the efficiency of perovskite cell devices with Spiro-OMeTAD as the organic hole transport layer is over 23% (Science, 2020,370, 74). The Seok topic group has a perovskite cell device with Spiro-OMeTAD as an organic hole transport layer in 2020, and the efficiency with the best performance is up to 25.17% (the certified efficiency is 24.4%). The initial efficiency of the unpackaged device remained over 80% after 1300 hours in a dark environment at 85 ℃ (Science, 2020,370, 108-112).
Although the research is extensive, the self hole mobility is low, and the hole mobility and the conductivity of the material must be improved by doping in a high-efficiency system, which makes the preparation and manufacturing of the device troublesome and is not beneficial to the subsequent industrial production, so that the high-mobility organic hole transport material becomes an important direction of research.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides the six-arm star-shaped material taking the truxene as the core, and the star-shaped material is used as a hole transport layer in the perovskite cell device, so that the hole mobility can be improved, and the photoelectric conversion efficiency of the perovskite cell device can be improved.
The invention is realized by the following technical scheme:
in a first aspect of the present invention, there is provided a six-arm star material with truxene as a core, having the following structure:
wherein Ar is a high hole mobility cell; r is selected from H, C1-C50 straight-chain alkyl or branched-chain alkyl; ar is more than one of benzene, anisole, diphenylamine, dimethoxydiphenylamine, triphenylamine, trimethoxytriphenylamine, carbazole, 3, 6-bis (dimethoxydiphenylamine) carbazole, 3, 6-bis (trimethoxytriphenylamine) carbazole and derivatives of all the structures.
Further, the conjugated unit Ar is selected from the following structures:
the chemical reaction flow for preparing the six-arm star-shaped material taking the truxene as the core is as follows:
the specific reaction steps and reaction conditions are as follows:
synthetic route and reaction conditions thereof: (i) iodine simple substance, iodobenzene and dichloromethane are protected from light; (ii) Thiophene tributyltin, tetrakis (triphenylphosphine palladium), N-dimethylformamide, 100 ℃; (iii) N-bromosuccinimide, chloroform, glacial acetic acid, and room temperature; (iv) ferric chloride, nitromethane, dichloromethane, 0 ℃; (v) Pinacol ester of 4-methoxyphenylboronic acid, tetrakis (triphenylphosphine palladium), potassium phosphate, N-dimethylformamide; (vi) Pinacol ester of N, -2 (4-methoxybenzene) phenylboronic acid, tetrakis (triphenylphosphine palladium), potassium phosphate, N-dimethylformamide.
In a second aspect of the invention, the six-arm star material with the truxene as the core is used as a hole transport layer in the preparation of a perovskite solar cell.
In a third aspect of the present invention, there is provided a perovskite battery device, which comprises, in order from bottom to top: ITO glass, a hole transport layer, a perovskite layer, a fullerene layer, a BCP layer and an Ag electrode; the hole transport layer is a six-arm star-shaped material taking triindene as a core.
The preparation method of the perovskite battery device comprises the following steps:
(1) Cleaning an ITO glass sheet, dissolving a six-support-arm star-shaped material taking indene trimer as a core in chlorobenzene, spin-coating on the ITO sheet, and then carrying out thermal annealing to obtain an ITO/hole transport layer;
(2) Spin-coating a perovskite layer on the ITO/hole transport layer, adding chlorobenzene as an anti-solvent at 12s, and performing thermal annealing after spin-coating to obtain the ITO/hole transport layer/perovskite layer;
(3) PCBM is prepared into chlorobenzene solution, the chlorobenzene solution is coated on the ITO/hole transport layer/perovskite layer in a spinning mode, and thermal annealing is carried out immediately to obtain an ITO/hole transport layer/perovskite layer/fullerene layer;
(4) Preparing BCP into an ethanol solution, and spin-coating the ethanol solution on the ITO/hole transport layer/perovskite layer/fullerene layer to obtain an ITO/hole transport layer/perovskite layer/fullerene layer/BCP layer;
(5) And performing silver electrode evaporation on the ITO/hole transport layer/perovskite layer/fullerene layer/BCP layer to obtain the perovskite battery device.
Preferably, in the step (1), the concentration of the star-shaped material with six arms and taking the truxene as the core is 5mg/mL; the thermal annealing temperature was 100 ℃ and the time was 10 minutes.
Preferably, in the step (2), the thermal annealing is 50 ℃ thermal annealing for 2 minutes, and then the temperature is raised to 100 ℃ thermal annealing for 10 minutes.
Preferably, in the step (3), the concentration of the PCBM is 20mg/mL; the thermal annealing temperature was 100 ℃ and the time was 10 minutes.
Preferably, in step (4), the concentration of BCP is 0.5mg/mL.
In a fourth aspect of the invention, there is provided the use of a material as described above in a perovskite cell device for photoelectric conversion.
The beneficial effects of the invention are as follows:
the invention designs a novel organic hole transport layer small molecular material which is in a six-arm star-shaped structure with truxene as a core, has good planarity and high hole mobility, can be used as a hole transport layer to be applied to organic photoelectric devices, and obviously improves the performance of the devices. The perovskite solar cell device with excellent performance is prepared as a hole transport layer, so that the photoelectric conversion efficiency of the perovskite solar cell device is improved, and the application prospect of the perovskite solar cell device is developed.
Drawings
FIG. 1 is a NMR spectrum of Tr-6-3PhO prepared in step (4) of example 1.
Fig. 2 is a schematic structural view of the perovskite cell device in example 2, in which 1 is ITO glass, 2 is a hole transport layer, 3 is a perovskite layer, 4 is a fullerene layer, 5 is a BCP layer, and 6 is an Ag electrode.
Fig. 3 is a current density-voltage curve for the perovskite cell device of example 2.
Detailed Description
It should be noted that the following detailed description is exemplary and is intended to provide further explanation of the disclosure. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs.
In order to make the technical solutions of the present application more clearly understood by those skilled in the art, the technical solutions of the present application will be described in detail below with reference to specific embodiments. If the experimental conditions not specified in the examples are specified, they are generally according to the conventional conditions or according to the conditions recommended by the reagents company; reagents, consumables and the like used in the following examples are commercially available unless otherwise specified.
Example 1
The synthesis route is as follows:
(1) Synthesis of compound 1 in formula ii:
1-Indenone (20.0 g, 151mmol) was dissolved in a mixed solution of glacial acetic acid (120 mL) and concentrated hydrochloric acid (60 mL) and heated to 120 ℃ under reflux for 24 hours with vigorous stirring. After the reaction, the reaction solution was directly poured into 1L of ice water, and sodium carbonate solid was added to neutralize the acid, and a yellow precipitate was precipitated after about one hour. The yellow precipitate was washed with water, acetone and dichloromethane to give a white solid (11g, 75%). This compound (10g, 29mmol) was placed in a 500mL two-necked flask, purged three times, tetrahydrofuran (200 mL) was injected under an argon atmosphere, and the reaction flask was placed at-78 ℃ and vigorously stirred. N-butyllithium (115.2mL, 2.5M) was added dropwise to the above solution at-78 ℃ and the reaction was carried out for 2h at low temperature. After completion of the reaction, 1-bromon-hexane (48.2 g) was added to the reaction solution, and then the reaction solution was warmed to room temperature and stirred at room temperature overnight. After the reaction, the reaction solution was poured into 1L of saturated NH 4 Aqueous Cl to quench excess n-butyllithium. The aqueous phase was extracted with ethyl acetate, and the extracted organic phase was dried over anhydrous magnesium sulfate. And (3) drying the solvent by spinning, mixing the crude product with powder, and performing column chromatography purification, wherein an eluent is n-hexane to obtain a white solid. 1 H NMR(500MHz,CDCl 3 )δ:8.18(d,3H),7.56(d,3H),7.52(dd,3H),2.87(m,6H),2.04(m,6H),0.93(m,36H),0.63(m,18H),0.46(m,14H). 13 C NMR(125MHz,CDCl 3 )δ:156.02,145.04,139.00,137.77,129.51,126.04,125.66,121.18,56.13,36.95,31.59,29.51,24.02,22.40,14.01。
(2) Synthesis of compound 2 in formula ii:
compound 1 (2.00g, 2.4mmol), iodobenzene (4.26g, 9.9mmol) and elemental iodine (2.11 g,8.27 mmol) was placed in a two-necked flask, evacuated three times, and 100mL of dichloromethane was added, protected from light overnight at room temperature. After the reaction is finished, 50mL of methanol is poured into the reaction liquid, precipitate is separated out, suction filtration is carried out, methanol is used for washing, tetrahydrofuran and methanol are used for recrystallization, and finally white powdery solid is obtained, wherein the reaction yield is up to 90%. 1 H NMR(500MHz,CDCl3)δ:8.53(s,3H),7.68(s,3H),2.73(m,6H),2.07(m,6H),0.95(m,36H),0.67(m,18H),0.44(m,12H). 13 C NMR(125MHz,CDCl 3 )δ:155.33,146.04,141.63,136.76,135.04,133.29,105.92,105.16,56.05,36.64,31.54,29.45,24.07,22.45,14.09。
(3) Synthesis of Tr-6-1PhO in formula II:
compound 2 (624 mg), pinacol ester of 4-methoxyphenylboronic acid (842.4 mg), tetrakis (triphenylphosphine-palladium) (46 mg), K 3 PO 4 (2.04 g) was placed in a two-necked round-bottomed flask, and then, purging was carried out three times, and then, 10mLDMF was added thereto, and the reaction was carried out at 105 ℃ overnight. Quench with water, precipitate filter, methanol rinse, column chromatography separation with DCM: PE = 1. 1 HNMR(500MHz,CDCl 3 )δ:8.39(s,3H),7.47(s,3H),7.24(m,6H),7.19(m,6H),6.88(m,6H),6.84(m,6H),3.84(m,18H),3.00(m,6H),2.23(m,6H),0.99(m,36H),0.74(m,12H),0.66(m,18H). 13 C NMR(125MHz,CDCl 3 )δ:158.78,158.68,153.20,145.79,139.82,138.76,138.62,138.43,135.60,135.06,131.56,131.54,131.49,131.47,127.23,124.49,113.85,113.82,113.72,113.69,56.06,55.59,55.56,37.44,31.98,29.98,24.48,22.80,14.19
(4) Synthesis of Tr-6-3PhO in formula II:
312mg of Compound 3, 776mg of N, -2 (4-methoxybenzene) phenylboronic acid pinacol ester, 23mg of tetrakis (triphenylphosphine palladium), 1.02g of potassium phosphate were placed in a two-necked round-bottomed flask, purged three times, added with 10mL of DMF, and reacted at 105 ℃ overnight. Quench with water, precipitate filter, methanol rinse, column chromatography separation with DCM: PE = 3. 1 H NMR(500MHz,CDCl 3 )δ:8.34(s,3H),7.43(s,3H),7.09(m,72H),3.81(s,36H),2.95(m,6H),2.16(m,6H),0.93(m,36H),0.69(m,12H),0.61(m,18H). 13 C NMR(125MHz,CDCl 3 )δ:156.10,152.99,145.64,139.64,138.56,138.43,131.09,126.82,120.46,115.03,55.90,37.35,31.91,29.94,24.39,22.74,14.38。
(5) Synthesis of compound 3 in formula ii:
compound 2 (2.00g, 1.25mmol), thiophene-3-butyltin (3.79g, 10mmol) and Pd (PPh) 3 ) 4 (210 mg) was placed in a two-necked flask, and the flask was degassed three times, 100mL of DMF was added, and the reaction was allowed to proceed overnight at 100 ℃. After the reaction is finished, the mixed solution is extracted by dichloromethane, an organic phase is dried by MgSO4, concentrated and separated by column chromatography, and recrystallized by using petroleum ether as an eluent to obtain a white solid 3 with the yield of about 75%. 1 HNMR(500MHz,CDCl 3 )δ:8.49(s,3H),7.57(s,3H),7.36(m,6H),7.05(m,6H),6.99(m,6H),2.95(m,6H),2.18(m,6H),0.98(m,36H),0.66(m,30H). 13 C NMR(125MHz,CDCl 3 )δ:153.71,146.16,146.14,143.94,143.59,140.03,137.90,132.20,131.73,127.30,127.25,127.17,127.14,127.09,125.94,125.69,124.66,56.06,37.06,31.57,29.56,24.11,22.48,14.11。
(6) Synthesis of compound 4 in formula ii:
adding compound 3 (0.4 g) and NBS (0.35 g) into 10mL of mixed solution of chloroform and acetic acid, reacting overnight at normal temperature in dark place, changing the reaction solution to light yellow the next day, pouring into water, stirring, adding sodium carbonate, DCM for extraction, and using MgSO as organic phase 4 Drying, concentrating, separating by column chromatography, and recrystallizing with petroleum ether as eluent to obtain white solid with a yield of 90%. 1 HNMR(500MHz,CDCl 3 )δ:8.38(s,3H),7.49(s,3H),7.04(m,6H),6.78(m,6H),2.86(m,6H),2.17(m,6H),0.95(m,36H),0.65(m,30H). 13 C NMR(125MHz,CDCl 3 )δ:154.23,146.50,144.82,144.44,140.23,137.65,131.47,130.85,130.41,130.18,127.78,127.56,127.54,127.18,124.54,112.82,112.48,56.13,36.97,31.58,29.52,24.11,22.47,14.11。
(7) Synthesis of compound 5 in formula ii:
compound 4 (0.41 mg) was dissolved in 180mL of dichloromethane, and 0.657mg of ferric chloride was dissolved in 10mL of nitromethane, and the resulting dichloromethane solution was added to the ferric chloride solution at 0 ℃ to react for one quarter of a second. Pouring the reaction mixture into methanol to obtain white powder, and pumpingFiltering, washing with methanol, and drying to obtain the final product with yield over 90%. 1 H NMR(500MHz,CDCl 3 )δ:9.09(s,3H),8.11(s,3H),7.69(s,6H),3.22(s,6H),2.48(s,6H),1.02(m,66H). 13 C NMR(125MHz,CDCl 3 )δ:153.74,147.31,139.59,138.22,137.96,136.88,132.34,131.91,126.11,125.94,125.39,125.26,119.93,117.05,114.34,113.68,56.32,37.72,31.61,29.66,24.55,22.35,13.93。
(8) Synthesis of FTr-6-2PhO in formula II:
compound 5 (364 mg), 4' -dimethoxydiphenylamine (413 mg), tris (dibenzylideneacetone) dipalladium (11 mg), potassium tert-butoxide (173 mg), tri-tert-butylphosphine (4.85 mg) were placed in a two-necked round-bottomed flask, and then air-purged three times, 10mL of toluene was added thereto, and the reaction was allowed to proceed overnight at 100 ℃. The mixture was extracted with dichloromethane and the organic phase was MgSO 4 Drying, concentrating and separating by column chromatography, and recrystallizing by using EA: PE = 1. 1 H NMR(500MHz,CDCl 3 )δ:8.87(s,3H),7.86(s,3H),7.27(m,24H),6.92(m,24H),6.80(s,3H),6.74(m,3H),3.83(d,36H),3.13(m,6H),2.29(m,6H),0.91(m,36H),0.65(m,12H),0.64(m,18H). 13 C NMR(125MHz,CDCl 3 )δ:157.33,157.01,154.56,153.42,152.75,146.73,141.84,141.57,138.96,138.74,132.97,132.07,129.73,127.52,126.45,125.88,119.81,116.71,115.31,115.21,111.61,109.10,56.32,56.11,56.09,38.10,32.06,30.07,24.91,22.89,14.26。
(9) Synthesis of FTr-6-3PhO in formula II:
compound 5 (364 mg), pinacol ester of N, N, -2 (4-methoxybenzene) phenylboronic acid (776 mg), tetrakis (triphenylphosphine-palladium) (23 mg), K 3 PO 4 (1.02 g) was placed in a two-necked round-bottomed flask, and then, purging was carried out three times, and then, 10mLDMF was added thereto, and the reaction was carried out at 105 ℃ overnight. Quench with water, precipitate filter, methanol rinse, column chromatography separation with DCM: PE = 8. 1 HNMR(500MHz,CDCl 3 )δ:9.25(s,3H),8.25(s,3H),7.89(s,6H),7.77(m,6H),7.70(m,6H),,7.18(m,24H),7.08(m,12H),6.92(m,24H),3.85(d,36H),3.34(m,6H),2.57(m,6H),1.04(m,12H),0.98(m,24H),0.80(m,12H),0.50(m,18H). 13 C NMR(125MHz,CDCl 3 )δ:156.32,153.22,146.88,144.05,143.70,140.69,140.54,139.20,138.44,135.88,135.56,134.45,134.19,133.95,127.26,127.21,127.03,126.09,125.90,120.62,120.14,118.77,117.34,117.10,114.92,114.84,56.19,55.68,55.67,37.85,31.71,29.78,24.62,22.41,13.98。
Example 2
Preparing a perovskite solar cell device:
first prepare MA 0.7 FA 0.3 PbI 3 Perovskite layer from 1.36M PbI in DMF solution 2 And 0.24M PbCl 2 Perovskite precursor solution of composition (called PbX) 2 ) And stirred at 75 ℃ for 2 hours. 70mg of MAI and 30mg of FAI were dissolved in the IPA solution, and the mixture was stirred at 50 ℃ for three hours to dissolve sufficiently.
The ITO sheet was washed and Plasma-stained, tr-6-1PhO, tr-6-3PhO, FTr-6-2PhO, and FTr-6-3PhO prepared in example 1 were dissolved in chlorobenzene at 5mg/mL, respectively, spin-coated at 5000 revolutions per second for 30 seconds, respectively, and then subjected to thermal annealing at 100 ℃ for 10 minutes.
The perovskite layer was spin-coated at 4000 rpm for 30s, and at 12s, 0.2mL of chlorobenzene was added as an anti-solvent, followed by thermal annealing at 50 ℃ for 2 minutes and 100 ℃ for 10 minutes.
PCBM was prepared as a 20mg/mL solution in chlorobenzene, spin-coated at 1000 rpm for 60s, and then thermally annealed at 100 ℃ for 10 minutes.
BCP was formulated as a 0.5mg/mL solution in ethanol and spun at 4000 rpm for 30s.
And finally, carrying out silver electrode evaporation to finish the preparation of the device, and respectively obtaining the perovskite solar cell devices taking Tr-6-1PhO, tr-6-3PhO, FTr-6-2PhO and FTr-6-3PhO as hole transport layers, which are marked as Tr-6-1PhO devices, tr-6-3PhO devices, FTr-6-2PhO devices and FTr-6-3PhO devices.
Example 3
The device prepared in example 2 was subjected to a J-V curve test with an AM 1.5G simulated solar lamp of 100mW cm -2 Under illumination; relevant parameters of the devices prepared above are shown in table 1.
TABLE 1 optimized data for the device
As can be seen from the current density-voltage curves of the perovskite cell devices in the table 1 and the graph 3, when the hole transport layer is Tr-6-3PhO, the perovskite solar cell device can obtain the open-circuit voltage of 1.07V under the condition of positive and negative scanning, and the short-circuit current is improved to 20.5mA cm -2 The filling factor is up to 78%, the photoelectric conversion efficiency is up to 17.1%, and no hysteresis effect exists. Therefore, the six-arm star-shaped material with the truxene as the core is a good hole transport material and is a perovskite solar cell material with excellent performance.
The above description is only a preferred embodiment of the present application and is not intended to limit the present application, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, improvement and the like made within the spirit and principle of the present application shall be included in the protection scope of the present application.
Claims (4)
2. use of the hexa-arm star material with indene trimer as core according to claim 1 as a hole transport layer in the preparation of perovskite solar cells.
3. A perovskite battery device, comprising in order from bottom to top: ITO glass, a hole transport layer, a perovskite layer, a fullerene layer, a BCP layer and an Ag electrode; the hole transport layer is the hexa-arm star material with the truxene as the core in claim 1;
the preparation method comprises the following steps:
(1) Cleaning an ITO glass sheet, dissolving the hexa-arm star material taking the truxene as the core in claim 1 in chlorobenzene, spin-coating on the ITO sheet, and then carrying out thermal annealing to obtain an ITO/hole transport layer; dissolving a six-arm star-shaped material taking the truxene as a core in chlorobenzene according to the concentration of 5mg/mL; the thermal annealing temperature is 100 ℃, and the time is 10 minutes;
(2) Spin-coating a perovskite layer on the ITO/hole transport layer, adding chlorobenzene as an anti-solvent at 12s, and performing thermal annealing after spin-coating to obtain the ITO/hole transport layer/perovskite layer; the thermal annealing is thermal annealing at 50 ℃ for 2 minutes, and then the temperature is raised to 100 ℃ for 10 minutes;
(3) PCBM is prepared into chlorobenzene solution, the chlorobenzene solution is coated on the ITO/hole transport layer/perovskite layer in a spinning mode, and thermal annealing is carried out immediately to obtain an ITO/hole transport layer/perovskite layer/fullerene layer; the concentration of PCBM is 20mg/mL; the thermal annealing temperature is 100 ℃, and the time is 10 minutes;
(4) Preparing BCP into an ethanol solution, and spin-coating on the ITO/hole transport layer/perovskite layer/fullerene layer to obtain an ITO/hole transport layer/perovskite layer/fullerene layer/BCP layer; the concentration of BC P is 0.5mg/mL;
(5) And carrying out silver electrode evaporation on the ITO/hole transport layer/perovskite layer/fullerene layer/BCP layer to obtain the perovskite battery device.
4. Use of the perovskite cell device as defined in claim 3 in photoelectric conversion.
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