CN114835731A - Organic n-type semiconductor material based on dimethylamino substituted naphthalimide-bithiophene and preparation method and application thereof - Google Patents
Organic n-type semiconductor material based on dimethylamino substituted naphthalimide-bithiophene and preparation method and application thereof Download PDFInfo
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Abstract
The application discloses an organic n-type semiconductor material based on dimethylamino substituted naphthalimide-bithiophene and a preparation method and application thereof, in particular to an n-type organic conjugated semiconductor material based on dimethylamino substituted naphthalimide as an electron pulling unit and bithiophene as an electron donating unit, a preparation method thereof and application thereof as a cathode interface modification layer material in a perovskite solar cell. The organic n-type semiconductor material based on dimethylamino substituted naphthalimide-bithiophene disclosed by the application has the advantages of solution-soluble processing, high electron mobility, excellent thermal stability, appropriate energy level and the like, and is an ideal perovskite solar cell electron transport layer material.
Description
Technical Field
The application belongs to the technical field of materials, and particularly relates to a dimethylamino-substituted naphthalimide-bithiophene semiconductor micromolecule material, a preparation method and application thereof, and application of the dimethylamino-substituted naphthalimide-bithiophene semiconductor micromolecule material serving as an electron transport layer in a perovskite solar cell.
Background
Solar energy is an inexhaustible clean and green energy, and in recent years, with the importance of energy problems of all countries in the world, solar cells become a research hotspot in the field. Compared with the traditional semiconductor solar cell, the perovskite solar cell has the outstanding advantages of low cost, high efficiency, simple manufacturing process, capability of being prepared into a flexible device and the like, and has wide development and application prospects 1-3 . Since 2013, Perovskite Solar Cells (PSCs) have undergone tremendous development, with Photoelectric Conversion Efficiencies (PCEs) above 22% 4 . In the recent time, researchers have focused on stability enhancement of PSCs, inexpensive large area fabrication and fabrication of flexible devices 5 , 6 . To achieve inexpensive large area flexible PSC, the inverted structure is TiO free due to its lack of 2 Therefore, the device can be prepared at low temperature and is very suitable for manufacturing large-area flexible devices 7 . A number of experiments have demonstrated that the optimized typical inverted device structure is: ITO/hole transport layer/perovskite/electron transport layer/hole blocking layer/Ag. In these devices, the use of a bilayer structure as an interfacial layer between the perovskite and Ag is relatively complex, consisting of C 60 A50 nm thick interfacial layer of (40nm) and BCP (10nm) also needs to be prepared by high vacuum evaporation, which is costly. PCBM or fullerene derivatives are expensive and are unstable to light and oxygen for long periods of time. In order to further simplify and reduce the manufacturing cost of devices and improve the stability of batteries, it is important to search for high-efficiency and stable electron transport materials or cathode interface modification layer materials with solution processability to replace the double-layer electron transport layers.
The electron transport material or the cathode interface modification layer material must meet three requirements, 1) energy level matching with the perovskite material; 2) excellent electron mobility; 3) can be processed by solution. Organic n-type semiconductor small molecules may be a better choice because of their strong energy level tunability, high electron mobility and excellent film-forming properties.
It has been demonstrated that compounds of the parent unit of Naphthalimide (NDI) are in the form of organic field effect crystalsExhibit excellent n-type semiconductor properties in transistor and organic photovoltaic cells 10 . Among them, high mobility Naphthalene Diimide (NDI) -thiophene, which is expected to be a suitable electron transport material for PSC, has a low Lowest Unoccupied Molecular Orbital (LUMO) level of-3.9 eV and a Highest Occupied Molecular Orbital (HOMO) level of about-6.0 eV 11 . Its LUMO energy level is in accordance with perovskite CH 3 NH 3 PbI 3 Or CH 3 NH 3 PbCl x I 3-x The LUMO levels of (a) are well matched, and in addition, the lower HOMO level is effective in preventing hole transfer to the cathode.
The method designs and synthesizes dimethylamino substituted naphthalimide-bithiophene, and the dimethylamino substituted naphthalimide-bithiophene is obtained by coupling Suzuki with bromo-and bithiophene. They are used as electron transport layer materials for applying to ITO/NiO of inverted device x And preparing a high-efficiency perovskite solar cell device from the perovskite/electron transport layer material 3/Ag.
Disclosure of Invention
The purpose of the invention is as follows: in order to overcome the defects in the prior art, the application provides an organic n-type semiconductor material based on dimethylamino substituted naphthalimide-bithiophene, and a preparation method and application thereof, and the organic n-type semiconductor material has the advantages of high electron mobility, proper energy level, solution processability, excellent film-forming property and the like.
The technical scheme is as follows: in order to achieve the above object, the present application provides an organic n-type semiconductor material based on dimethylamino substituted naphthalimide-bithiophene, wherein the general structural formula of the material includes:
wherein R is 1 、R 2 Each independently is an alkyl group C n H 2n+1 Wherein n is 0 to 12.
In one embodiment, R in the general structural formula of the organic n-type semiconductor material based on dimethylamino-substituted naphthalimide-bithiophene 1 、R 2 Each independently selected from: H.CH 3 、CH 2 CH 3 、(CH 2 ) 2 CH 3 、(CH 2 ) 3 CH 3 、(CH 2 ) 4 CH 3 、(CH 2 ) 5 CH 3 、(CH 2 ) 6 CH 3 、(CH 2 ) 7 CH 3 、(CH 2 ) 8 CH 3 、(CH 2 ) 9 CH 3 、(CH 2 ) 10 CH 3 、(CH 2 ) 11 CH 3 。
in one embodiment, the organic n-type semiconductor material based on dimethylamino-substituted naphthalimide-bithiophene is R 1 Is CH 2 CH 3 ，R 2 Is C 4 H 9 。
The application also provides a preparation method of the organic n-type semiconductor material based on dimethylamino substituted naphthalimide-bithiophene, which comprises the following steps:
step one, preparing a 4-bromo-9- (dimethylamino) -naphthalimide intermediate, namely, preparing 4,9 dibromo 2, 7-bicH 2 CHR 1 R 2 Naphthalimides, dry K 2 CO 3 Adding the mixture into a reaction container, adding DMF, reacting at 80-120 ℃ for 1-24 hours, standing, filtering to obtain mother liquor, removing excess solvent through reduced pressure distillation, and purifying through a column to obtain the 4-bromo-9- (dimethylamino) -naphthalimide intermediate;
step two, preparing an organic conjugated n-type semiconductor material of dimethylamino substituted naphthalimide and bithiophene, and adding the 4-bromo-9- (dimethylamino) -naphthalimide intermediate 2 and 5,5 '-ditrimethyltin-2, 2' -bithiophene obtained in the step one into a reaction vessel; pd (PPh) 3 ) 4 As a catalyst, anhydrous toluene is used as a solvent; introducing inert gas to discharge air in the reaction container, and carrying out reflux reaction for 12-72 hours at 110 ℃ under the condition of keeping out of the sun to obtain a reaction mixture; and standing and filtering the reaction mixture to obtain a mother solution, and purifying by a silica gel column to obtain the organic conjugated n-type semiconductor material of the dimethylamino substituted naphthalimide and the bithiophene.
In a real worldIn the embodiment, in the first step, K 2 CO 3 And 4,9 dibromo 2, 7-di-CH 2 CHR 1 R 2 The molar ratio of the naphthalene imide is 0.1: 1-10: 1.
In one embodiment, in step one, 2, 7-dicarch is dibromo-4, 9-dicarbo 2 CHR 1 R 2 The amount of the naphthalimide added with DMF is 100 mL-10000 mL.
In one embodiment, in the second step, the molar ratio of the 4-bromo-9- (dimethylamino) -naphthalimide intermediate to 5,5 '-bistrimethyltin-2, 2' -bithiophene is 2:1 to 4: 1.
In one embodiment, in the second step, the Pd (PPh) 3 ) 4 The molar ratio of the catalyst to the 4-bromo-9- (dimethylamino) -naphthalimide intermediate is 3-12%, and the amount of the anhydrous toluene is 100-1000 mL per mole of the 4-bromo-9- (dimethylamino) -naphthalimide intermediate.
In one embodiment, the reaction equation of the first step is:
in one embodiment, the reaction equation in the second step is:
the application also provides an application of the organic n-type semiconductor material based on dimethylamino substituted naphthalimide-bithiophene in the perovskite solar cell, which is characterized in that the small molecular semiconductor material of the dimethylamino substituted naphthalimide and the bithiophene is used as a single-layer electron transport layer material in the perovskite solar cell.
In one embodiment, the application of the organic n-type semiconductor material based on dimethylamino substituted naphthalimide-bithiophene in the perovskite solar cell is characterized in that: the preparation method of the perovskite solar cell device comprises the following steps:
washing and drying the ITO glass to be used as an anode electrode, and spin-coating the ITO glass to generate a hole transport layer NiO with the thickness of 10-30nm x ；
At the NiO x Preparing a 250-400nm perovskite layer on the layer;
spin-coating on the perovskite layer to generate a cathode modification layer with the thickness of 1-5nm as an electron transport layer;
and evaporating 80-120nm of metal Ag on the cathode modification layer to be used as a cathode electrode.
Has the advantages that: compared with the prior art, the organic n-type semiconductor material based on dimethylamino substituted naphthalimide-bithiophene and the application thereof have the following advantages: the organic conjugated n-type semiconductor using the naphthalimide and the thiophene, disclosed by the application, is based on that dimethylamino replaces the naphthalimide or derivatives thereof as an electron-withdrawing unit and the bithiophene is an electron-donating unit, and a side chain is added to the naphthalimide to optimize related performances, so that the organic conjugated n-type semiconductor has the advantages of high mobility, excellent thermal stability, appropriate energy level and the like, and is an ideal electron transport layer material of the perovskite solar cell.
Drawings
FIG. 1 is a diagram of the structure of a small molecule prepared in an example;
FIGS. 2a and 2b are the hydrogen spectra of the small molecule NMR prepared by the example;
FIG. 3 is a cyclic voltammogram of a polymer prepared in the example;
FIG. 4 shows the absorption spectrum in the UV-visible region of a methylene chloride solution of a polymer prepared in accordance with an example;
FIG. 5 is a J-V curve for a device made using example small molecules as the electron transport layer material.
Detailed Description
The application discloses an organic n-type semiconductor material based on dimethylamino substituted naphthalimide-bithiophene and application thereof. The n-type conjugated polymer semiconductor based on the naphthalimide and the selenophene derivative has the advantages of being soluble in solution, high in electron mobility, excellent in thermal stability and appropriate in energy level, and is an ideal electron transport layer material of the perovskite solar cell.
The following is a detailed description of the embodiments of the present application, which are implemented on the premise of the technical solution of the present application, and detailed implementation and specific operation procedures are given, but the scope of the present application is not limited to the following examples.
Examples
The present application can be better understood in light of the following examples. However, those skilled in the art will readily appreciate that the specific material ratios, process conditions, and results thereof described in the examples are illustrative only and should not be taken as limiting the application as detailed in the claims.
The embodiment of the application utilizes an organic conjugated micromolecule n-type semiconductor material which is formed by taking planar rigid naphthalimide as a strong electron-withdrawing unit and taking thiophene with strong conductivity as an electron-donating unit and a preparation method thereof, and is shown in figure 1. The structures of the polymers and the intermediates thereof are represented by nuclear magnetism and mass spectra, the thermal stability of the polymers and the intermediates thereof is analyzed by thermogravimetry, the electrochemical properties of the polymers and the energy level of the polymers are represented by cyclic voltammetry, the photophysical properties of the polymers and the energy level of the polymers are represented by an ultraviolet-visible light spectrophotometer, and the electron mobility of the polymers and the intermediates thereof is calculated by a space charge confinement method. The structure shows that the material has high electron mobility, good light absorption, excellent thermal stability and proper energy level. The materials are used as electron transport layer materials to prepare perovskite solar cell devices.
(1) Preparation of 4-bromo-9- (dimethylamino) -naphthalimide intermediate (2)
The raw materials 4,9 dibromo 2, 7-diisooctyl naphthalimide 1(0.63g, 1mmol) and K 2 CO 3 (0.2g, 1.5mmol) was added to a dry one-neck flask (100mL) in DMF (5mL) and reacted at 85 ℃ for 8 h. Standing and filtering to obtain mother liquor after reaction, removing excessive solvent by reduced pressure distillation, and processing with silica gelColumn purification (using petroleum ether/dichloromethane ═ 3:1 eluent) gave the final product (2) (0.17g, 0.26mmol) as a dark red solid in 26.9% yield. 1 H NMR(400MHz，CDCl 3 )：δ[ppm]＝8.88(1H，s)，8.56(1H，s)，4.18-4.13(4H，m)，3.27(6H，s)，4.18-4.07(8H，m)，3.27(12H，s)，1.41-1.25(16H，m)，0.98-0.88(12H，m)。
(2) Preparation of dimethylamino-substituted naphthalimide and dithiophene micromolecule semiconductor (3)
4-bromo-9- (dimethylamino) -naphthalimide intermediate (2) (0.61g, 1mmol) and 5,5 '-bistrimethyltin-2, 2' -bithiophene in a molar ratio of 2.5:1 were added to a dry two-necked flask (100mL) and 6% molar Pd (PPh) was added 3 ) 4 Adding 30mL of anhydrous toluene as a solvent into the catalyst, introducing inert gas to discharge air in a reaction container, and carrying out reflux reaction for 24 hours at 110 ℃ under the condition of keeping out of the light. The reaction mixture was allowed to stand, filtered to obtain a mother liquor, and purified by a silica gel column (petroleum ether: CH) 2 Cl 2 1:1 as eluent) was further purified to give 0.248g of a shiny black blue solid in 50.5% yield. 1 H NMR(400MHz，CDCl 3 )：δ[ppm]＝8.66(2H，s)，8.54(2H，s)，7.25(2H，d，J 1＝3.6Hz)，7.14(2H，d，J 1＝3.6Hz)，4.18-4.07(8H，m)，3.27(12H，s)，1.95-1.92(4H，m)，1.31-1.25(32H，m)0.94-0.86(24H，m)。
The reaction equation of the step I is as follows:
the reaction equation of the step II is as follows:
fabrication of perovskite solar cell devices
(1) Commercially available Indium Tin Oxide (ITO) glass is firstly cleaned by detergent and then sequentially cleaned by tap water, deionized water, ethanol, acetone and isopropanol through ultrasonic cleaning.
(2) Drying ITO, and spin-coating a 30 nm-thick hole transport layer NiO x And (5) standby.
(3) In NiO x Preparation of CH layer 300nm thick 3 NH 3 PbCl 0.1 I 2.9 A perovskite layer.
(3) The micromolecules 3 in the embodiment example are spin-coated on the perovskite layer to generate a cathode modification layer with the thickness of 4nm, and the effective area of an active layer of the solar device is 3.6mm 2 。；
(4) Under vacuum (2 x 10) -4 Pa) was deposited with 100nm of Ag as a cathode.
(5) Using a Newport 500W xenon lamp equipped with an AM1.5 filter as a simulated solar light source at 100mW/cm 2 Carrying out photovoltaic performance test under light intensity, wherein the light intensity is calibrated through a standard monocrystalline silicon solar cell; the J-V curve was measured using Keithley 260.
As shown in fig. 1, it is an n-type semiconductor molecular structural formula based on dimethylamino substituted naphthalimide and bithiophene.
As shown in fig. 2a and 2b, the nuclear magnetic resonance hydrogen spectrogram shows the integral number, integral ratio and chemical shift of hydrogen on the intermediate or target small molecule, and the structural formula of each product is determined.
As shown in FIG. 3, the electrochemical cyclic voltammogram of the target small molecule showed an oxidation potential of 0.69V and a reduction potential of-1.05V relative to ferrocene standard chemical.
As shown in FIG. 4, the absorption spectrum of the target small molecule in the dichloromethane solvent covers the visible region of 300-800 nm. The maximum absorption wavelengths are 609 nm.
As shown in FIG. 5, 100mW/cm 2 The J-V curve of the perovskite solar cell obtained by testing under the light intensity shows that the photoelectric conversion efficiency of the target micromolecule 3 electron transport layer material is 16.1 percent respectively.
The above is only the preferred embodiment of the present application, and it should be noted that: it will be apparent to those skilled in the art that various modifications and enhancements can be made without departing from the principles of the application, and such modifications and enhancements are intended to be included within the scope of the application.
Claims (10)
1. An organic n-type semiconductor material based on dimethylamino substituted naphthalimide-bithiophene is characterized in that the structural general formula of the material comprises:
wherein R is 1 、R 2 Each independently is an alkyl group C n H 2n+1 Wherein n is 0 to 12.
2. The organic n-type semiconductor material based on dimethylamino-substituted naphthalimide-bithiophene according to claim 1, wherein R in the general structural formula 1 、R 2 Each independently selected from: H. CH (CH) 3 、CH 2 CH 3 、(CH 2 ) 2 CH 3 、(CH 2 ) 3 CH 3 、(CH 2 ) 4 CH 3 、(CH 2 ) 5 CH 3 、(CH 2 ) 6 CH 3 、(CH 2 ) 7 CH 3 、(CH 2 ) 8 CH 3 、(CH 2 ) 9 CH 3 、(CH 2 ) 10 CH 3 、(CH 2 ) 11 CH 3 。
3. The organic n-type semiconductor material based on dimethylamino-substituted naphthalimide-bithiophene according to claim 1, wherein R in the general structural formula 1 Is CH 2 CH 3 ，R 2 Is C 4 H 9 。
4. The method for preparing an organic n-type semiconductor material based on dimethylamino-substituted naphthalimide-bithiophene according to claim 1, which comprises the following steps: the method comprises the following steps:
step one, preparing a 4-bromo-9- (dimethylamino) -naphthalimide intermediate, namely, preparing 4,9 dibromo 2, 7-bicH 2 CHR 1 R 2 Naphthalimide radical, dry K 2 CO 3 Adding the mixture into a reaction container, adding DMF, reacting at 80-120 ℃ for 1-24 hours, standing, filtering to obtain mother liquor, removing excess solvent through reduced pressure distillation, and purifying through a column to obtain the 4-bromo-9- (dimethylamino) -naphthalimide intermediate;
step two, preparing an organic conjugated n-type semiconductor material of dimethylamino substituted naphthalimide and bithiophene, and adding the 4-bromo-9- (dimethylamino) -naphthalimide intermediate 2 and 5,5 '-bistrimethyltin-2, 2' -bithiophene obtained in the step one into a reaction vessel; pd (PPh) 3 ) 4 As a catalyst, anhydrous toluene is used as a solvent; introducing inert gas to discharge air in the reaction container, and carrying out reflux reaction for 12-72 hours at 110 ℃ under the condition of keeping out of the sun to obtain a reaction mixture; and standing and filtering the reaction mixture to obtain a mother solution, and purifying by a silica gel column to obtain the organic conjugated n-type semiconductor material of the dimethylamino substituted naphthalimide and the bithiophene.
5. The method according to claim 4, wherein in the first step, K is 2 CO 3 And 4,9 dibromo 2, 7-di-CH 2 CHR 1 R 2 The molar ratio of the naphthalene imide is 0.1: 1-10: 1.
6. The method according to claim 4, wherein in the first step, 2, 7-dibrominated per mole of the 4, 9-dibrominated per mole of the 4, 7-bich 2 CHR 1 R 2 The amount of the naphthalimide added with DMF is 100 mL-10000 mL.
7. The preparation method according to claim 4, wherein in the second step, the molar ratio of the 4-bromo-9- (dimethylamino) -naphthalimide intermediate to 5,5 '-bistrimethyltin-2, 2' -bithiophene is 2:1 to 4: 1.
8. The method according to claim 4, wherein in the second step, the Pd (PPh) 3 ) 4 The molar ratio of the catalyst to the 4-bromo-9- (dimethylamino) -naphthalimide intermediate is 3-12%, and the amount of the anhydrous toluene is 100-1000 mL per mole of the 4-bromo-9- (dimethylamino) -naphthalimide intermediate.
9. The application of the dimethylamino substituted naphthalimide-bithiophene-based organic n-type semiconductor material in the perovskite solar cell as claimed in claim 1 is characterized in that the dimethylamino substituted naphthalimide-bithiophene-based organic n-type semiconductor material is applied as a single-layer electron transport layer material in the perovskite solar cell.
10. The use of a dimethylamino-substituted naphthalimide-bithiophene based organic n-type semiconductor material according to claim 9 in perovskite solar cells, characterized in that: the preparation method of the perovskite solar cell device comprises the following steps:
cleaning and drying ITO glass, then using the ITO glass as an anode electrode, and spin-coating the ITO glass to generate a hole transport layer NiO with the thickness of 10-30nm x ；
At the NiO x Preparing a 250-400nm perovskite layer on the layer;
spin-coating on the perovskite layer to generate a cathode modification layer with the thickness of 1-5nm as an electron transport layer;
and evaporating 80-120nm of metal Ag on the cathode modification layer to be used as a cathode electrode.
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