CN112961169B - Imide compound, preparation method thereof and application of perovskite solar cell - Google Patents

Imide compound, preparation method thereof and application of perovskite solar cell Download PDF

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CN112961169B
CN112961169B CN202011081011.9A CN202011081011A CN112961169B CN 112961169 B CN112961169 B CN 112961169B CN 202011081011 A CN202011081011 A CN 202011081011A CN 112961169 B CN112961169 B CN 112961169B
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solar cell
perovskite solar
hole transport
imide
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CN112961169A (en
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孙华
王士凡
董黎明
堵锡华
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Xuzhou University of Technology
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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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Abstract

The invention discloses an imide compound, a preparation method thereof and application of a perovskite solar cell, wherein the compound has a structure shown in a formula (I), has a large pi conjugated planar structure of bithiophene imide and a D-A-D type molecular structure, can effectively improve the photoelectric property of the compound, ensures that the compound has good pi-pi accumulation in a thin film state, further has good charge transmission property, further regulates the HOMO energy level of the material by introducing an arylamine structure into an end group, improves the hole mobility, and can be used as a hole transmission material for the perovskite solar cell. Meanwhile, the hole transport material has an imide structure which can further passivate a perovskite layer, so that the hole transport material has high photoelectric conversion efficiency. The invention also discloses a perovskite solar cell device, wherein at least one hole transport layer of the perovskite solar cell device contains the imide compound, and high photoelectric conversion efficiency can be obtained without doping.

Description

Imide compound, preparation method thereof and application of perovskite solar cell
Technical Field
The invention relates to the technical field of solar cells, and relates to an imide compound, a preparation method thereof and application of a perovskite solar cell.
Background
In 2009, a scientific research group led by japanese scientist Miyasaka reported for the first time solar cells (perovskite solar cells) based on organic-inorganic hybrid perovskites, and achieved a photoelectric conversion efficiency of 3.8%. After a decade of rapid development, perovskite solar cells have become the most attractive new energy technology. However, the stability of the perovskite solar cell is different from that of the conventional solar cell, and the improvement of the stability of the perovskite solar cell is the key for realizing the industrialization of the perovskite solar cell. As an important component of perovskite solar cells, the semiconducting properties of hole transport materials play a crucial role in the photoelectric conversion efficiency and stability of the cells. At present, PTAA or Spiro-OMeTAD is mostly used as a hole transport material for perovskite solar cells, however, due to the fact that steric hindrance of a main unit of the molecules is large, interaction of the molecules in a thin film is weak, hole mobility is low, and conductivity is poor, and therefore, the hole transport performance needs to be improved by doping additives such as organic lithium salt. However, such doping additives are sensitive to water and oxygen, and the prepared devices have poor stability and high price, so that the commercial requirements cannot be met. Therefore, the design and development of the low-cost and high-efficiency non-doped organic hole transport material have important significance for improving the stability of the perovskite solar cell and reducing the manufacturing cost of the cell.
Disclosure of Invention
The invention aims to provide an imide compound, a preparation method thereof and application of a perovskite solar cell, and aims to develop a series of hole transport materials with simple synthesis process and excellent hole transport property.
In view of the above technical problems, the present invention aims to provide an imide compound which has the advantages of simple synthesis, high charge mobility, good stability, etc., and can be applied to perovskite solar cells as a non-doped hole transport material.
The technical scheme of the invention is as follows:
an imide compound having the formula (I):
Figure BDA0002718707310000021
r1 is selected from C1-C30 substituted or unsubstituted alkyl, C2-C30 substituted or unsubstituted alkenyl, C2-C30 substituted or unsubstituted alkynyl, C3-C30 substituted or unsubstituted cycloalkyl, C6-C60 substituted or unsubstituted aryl, C3-C30 substituted or unsubstituted heteroaryl, C1-C30 substituted or unsubstituted alkoxy, and C1-C30 substituted or unsubstituted silyl; r2 is selected from hydrogen, deuterium, halogen, cyano, C1-C30 substituted or unsubstituted alkyl, C2-C30 substituted or unsubstituted alkenyl, C2-C30 substituted or unsubstituted alkynyl, C3-C30 substituted or unsubstituted cycloalkyl, C6-C60 substituted or unsubstituted aryl, C3-C30 substituted or unsubstituted heteroaryl, C1-C30 substituted or unsubstituted alkoxy, C1-C30 substituted or unsubstituted alkylthio, and C1-C30 substituted or unsubstituted silyl;
ar is an arylamine structural unit with an electron donating characteristic, and is specifically represented as a substituted or unsubstituted diphenylamine, triphenylamine, carbazole and other structural units.
Preferably, R1 is selected from a C1-C18 linear or branched alkyl group, or an alkyl polyether of the formula:
Figure BDA0002718707310000022
wherein R3, R4, R5 and R6 are alkyl groups with the number of C atoms less than 10, and n and m are less than or equal to 10.
Preferably, R2 is selected from hydrogen, fluorine atom, C1-C18 straight chain or branched chain alkyl, methoxy and methylthio.
Preferably, the Ar structural unit is selected from any one of the following structural units:
Figure BDA0002718707310000023
the imide containing structural formula includes, but is not limited to, the following compounds:
Figure BDA0002718707310000031
a perovskite solar cell device, at least one functional layer of the perovskite solar cell device contains the imide compound.
Preferably, the functional layer is a hole transport layer.
Compared with the prior art, the invention has the following remarkable advantages: 1. the organic compound based on a bithiophene imide structure is developed, the photoelectric characteristic of the compound can be effectively improved by utilizing the molecular design idea that bithiophene imide has a large pi-conjugated planar structure and D-A-D (donor unit-receptor unit-donor unit), the material is guaranteed to have good pi-pi accumulation in a film state, and further has good charge transfer characteristic, and meanwhile, the HOMO energy level of the material is further regulated and controlled by introducing an arylamine structure into an end group, so that the hole mobility is improved; 2. the material has the advantages of simple synthesis process and high yield, can be used as an undoped hole transport material to be applied to perovskite solar cells, shows high efficiency and excellent stability, has the potential of replacing the current hole transport material, and has good industrialization prospect.
Detailed Description
The invention is described in further detail below:
several embodiments will be given below to specifically explain the technical solution of the present invention. It should be noted that the following examples are only for the purpose of aiding understanding of the present invention, and are not intended to limit the present invention.
The synthesis route of the invention is as follows:
Figure BDA0002718707310000041
example 1
Synthesis of Compound C-1
Figure BDA0002718707310000042
Synthesis of Compounds 1-3:
firstly weighing 2.5g of compound 1-1, glacial acetic acid 20mL and 2.6g of compound 1-2, adding the mixture into a 50mL three-necked bottle, heating and refluxing for reaction for 20 hours, cooling to room temperature, pouring the mixture into a sodium carbonate solution, extracting by using dichloromethane, and purifying by using a silica gel column to obtain the compound 1-3, wherein the yield is 78%.
Synthesis of Compounds 1-5:
first, 2g of the compound 1 to 3, the compound 1 to 4 (2.2 equiv), tetrakistriphenylphosphine palladium (0.05 equiv), and 30mL of toluene were weighed and charged into a 100mL two-necked flask, nitrogen was replaced three times with a diaphragm pump, and after heating and refluxing for 20 hours, the mixture was cooled to room temperature, washed with water and extracted with dichloromethane, and purified with a silica gel column to obtain the compound 1 to 5, with a yield of 87%.
Synthesis of Compounds 1-6:
firstly weighing 2g of compound 1-5, chloroform 50mL, glacial acetic acid and adding into a 250mL double-mouth bottle, then adding NBS (2.2 equiv) in portions, stirring for 12 hours at room temperature, keeping out of the sun in the process, then pouring into water, extracting with dichloromethane, and purifying with a silica gel column to obtain the compound 1-6, wherein the yield is 80%.
Synthesis of Compounds 1-7:
firstly, 1g of compound 1-6, 250mL of toluene and 5 iodine granules are weighed and added into a 500mL flask, the mixture is stirred for 5 hours at room temperature under the illumination of 400nm, sodium sulfite solution is poured, dichloromethane is used for extraction, and silica gel column purification is carried out to obtain the compound 1-7, wherein the yield is 95%.
Synthesis of Compound C-1:
1g of Compound 1-7, compound 1-8 (4, 4-dimethoxydiphenylamine (0.82g, 2.5 equiv)), naOtBu (2.5 equiv), (t-Bu) were weighed out 3 P(0.12equiv),Pd 2 (dba) 3 (0.06 equiv) toluene 20mL was charged into a 50mL flask, nitrogen was replaced three times with a diaphragm pump, and after heating reflux reaction for 20 hours, cooling to room temperature, washing with water and extraction with dichloromethane, silica gel column purification gave compound C-1 with a yield of 85%.
Elemental analysis: theoretical value (C56H 55N3O6S 4): c,67.65; h,5.58; n,4.23; s,12.90; measured value: c,67.64; h,5.54; n,4.26; s,12.88, HRMS (ESI) M/z (M + 1) + : theoretical value: 994.29; measured value: 994.30.
Example 2
Synthesis of Compound C-2
Figure BDA0002718707310000061
The specific synthetic procedure and operation of compound C-2 were the same as those of compound C-1 except that compound 2-1 was used instead of compound 1-4 in example 1.
Compound C-2: elemental analysis: theoretical value (C58H 59N3O8S 4): c,66.07; h,5.64; n,3.99; s12.16; measured value: c,66.05; h,5.61; n,4.03; s,12.17, HRMS (ESI) M/z (M + 1) + : theoretical value: 1054.31; measured value: 1054.27.
example 3
Synthesis of Compound C-3
Figure BDA0002718707310000062
The specific synthetic procedure and operation of compound C-3 are the same as those of compound C-1 except that compound 3-1 is substituted for compound 1-2 and compound 3-3 is substituted for compound 1-4 in example 1.
Compound C-3: elemental analysis: theoretical value (C64H 71N3O6S 4): c,69.47; h,6.47; n,3.80; s,11.59 found: c,69.43; h,6.51; n,3.83; s,11.55, HRMS (ESI) M/z (M) + : theoretical values are as follows: 1105.42; measured value: 1105.43.
example 4
Synthesis of Compound C-4
Figure BDA0002718707310000071
The specific synthetic procedure and operation of compound C-4 are the same as those of compound C-3 except that compound 4-1 is substituted for compound 3-3 in example 3.
Compound C-4: elemental analysis: theoretical value (C74H 91N3O6S 4): c,71.29; h,7.36; n,3.37; s,10.29; measured value: c,71.27; h,7.33; n,3.39; s,10.31, HRMS (ESI) M/z (M) + : theoretical value: 1245.57; measured value: 1245.58.
examples 5 to 8
Synthesis of synthetic Compounds C-5 to C-8
Figure BDA0002718707310000072
The specific synthetic steps and operations of the compounds C-5, C-6, C-7 and C-8 are the same as those of the compounds C-1, C-2, C-3 and C-4, except that the compound 5-1 is used instead of the compound 1-8.
Example 9
Synthesis of Compound C-9
Figure BDA0002718707310000081
Synthesis of Compound C-9:
weighing 1g of Compound 1-7, compound 9-1 (2.5 equiv), K 2 CO 3 (3equiv),Pd 2 (PPh 3 ) 4 (0.1 equiv), water (10mL), THF (70mL) were added to a 200mL flask, nitrogen was replaced with a diaphragm pump three times, and after heating and refluxing for 20 hours, the mixture was cooled to room temperature, washed with water, extracted with dichloromethane, and purified with a silica gel column to give compound C-9 in a yield of 78%.
Elemental analysis: theoretical value (C68H 63N3O6S 4): c,71.24; h,5.54; n,3.67; s,11.19; measured value: c,71.21; h,5.52; n,3.71; s,11.16, HRMS (ESI) m/z: theoretical value: 1145.36; measured value: 1146.37 (M + 1) + 。
Examples 10 to 12
Synthesis of synthetic Compounds C-10 to C-12
Figure BDA0002718707310000091
The specific synthetic procedures and operations of the compounds C-10, C-11 and C-12 are the same as those of the compound C-9 except that the compounds 2-4, 3-5 and 4-4 are respectively substituted for the compounds 1-7.
Examples 13 to 16
Synthesis of synthetic Compounds C-13 to C-16
Figure BDA0002718707310000101
The specific synthetic procedures and operations of the compounds C-13, C-14, C-15 and C-16 are the same as those of the compounds C-9, C-10, C-11 and C-12, except that the compound 13-1 is used instead of the compound 9-1.
A hole transport layer in the perovskite solar cell is prepared on the basis of the compound, and is applied to the titanium ore solar cell, and the method specifically comprises the following steps:
and (3) testing a device:
the perovskite solar cell adopts an n-i-p structure, and the specific structure is as follows:
ITO/Electron transport layer (SnO) 2 PCBM)/perovskite layer (MA) 0.7 FA 0.3 PbI 2.85 Br 0.15 ) Hole transport layer (spiro-OMeTAD or a compound of the invention)/anode (Au)
Figure BDA0002718707310000102
Device example 1 (comparative example 1)
Substrate cleaning:
the ITO coated transparent motor substrate was sonicated in a commercial cleaner, rinsed in deionized water, in acetone: ultrasonic degreasing is carried out in an ethanol mixed solvent (volume ratio is 1.
Preparing a device:
spin coating 15nm SnO on ITO 2 (annealing at 180 ℃ for 1 hour) transferring the substrate into a glove box, and spin-coating 10nm PCBM (annealing at 100 ℃ for 10 minutes) as an electron transport layer; spin-coating 600nm perovskite layer (prepared by mixing MAI (0.7 mmol), FAI (0.3 mmol), pbI 2 (0.925mmol),PbBr 2 (0.075mmol),DMSO(71μL)，Pb(SCN) 2 (9.22 mg) was dissolved in DMF (1 mL) to make a spin-on solution), annealed at 100 ℃ for 5 minutes; the 40nm hole transport layer spiro-OMeTAD evaporated with 80nm gold as anode.
Device example 2 (comparative example 2)
This embodiment differs from device embodiment 1 in that: doping the hole transport layer spiro-OMeTAD of the perovskite solar cell device (doping with 4-tert-butylpyridine, lithium bis (trifluoromethanesulfonyl) imide).
Device example 3
This embodiment differs from device embodiment 1 in that: the hole transport material of the perovskite solar cell device is replaced by the compound C-1 (without doping).
Device example 4
This embodiment differs from device embodiment 1 in that: the hole transport material of the perovskite solar cell device is replaced by the compound C-2 (without doping).
Device example 5
This embodiment differs from device embodiment 1 in that: the hole transport material of the perovskite solar cell device is replaced by the compound C-3 (without doping) of the invention.
Device example 6
This embodiment differs from device embodiment 1 in that: the hole transport material of the perovskite solar cell device is replaced by the compound C-5 (without doping).
Device example 7
This embodiment differs from device embodiment 1 in that: the hole transport material of the perovskite solar cell device is replaced by the compound C-9 (without doping) of the invention.
Device example 8
This embodiment differs from device embodiment 1 in that: the hole transport material of the perovskite solar cell device is replaced by the compound C-10 (without doping) of the invention.
Device example 9
This embodiment differs from device embodiment 1 in that: the hole transport material of the perovskite solar cell device is replaced by the compound C-11 (without doping) of the invention.
Device example 10
This embodiment differs from device embodiment 1 in that: the hole transport material of the perovskite solar cell device is replaced by the compound C-15 (without doping) of the invention.
Device example 11
This embodiment differs from device embodiment 1 in that: the hole transport material of the perovskite solar cell device is replaced by the compound C-17 (without doping).
Device example 12
This embodiment differs from device embodiment 1 in that: the hole transport material of the perovskite solar cell device is replaced by the compound C-18 (without doping).
Test example 1
Testing the photovoltaic performance of the device: the effective area of the device is 0.4cm 2 . And (3) testing conditions are as follows: spectral distribution AM1.5G, illumination intensity 100mW/cm 2 AAA solar simulator (tokoro, tokyo), J-V curve was measured with Keithly model 2400 digital source meter, all devices were simply packaged with uv glue and tested for normal measurement in atmospheric environment.
The results are shown in Table 1.
Figure BDA0002718707310000121
Figure BDA0002718707310000131
Table 1 device example corresponding performance table
From the performances of the device examples, it can be seen that compared with the comparative examples, the hole transport material designed by the invention has better photoelectric conversion efficiency and better stability compared with the undoped spiro-OMeTAD without doping, the efficiency is comparable to or even exceeds that of the doped spiro-OMeTAD, and the stability is more than one order of magnitude, which indicates that the material disclosed by the invention has obvious performance advantages compared with the current hole transport material.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.
In conclusion, the organic compound based on the bithiophene imide structure and the arylamine unit is synthesized, and in the molecules, the bithiophene imide structure unit has good conjugation property and planarity, so that the prepared material can form effective pi-pi accumulation in a thin film, and further has good charge mobility. And by a molecular design strategy of D-A-D, an arylamine structure is modified at the end group of the bithiophene imide structural unit, the HOMO energy level of the material is further regulated and controlled, the hole characteristic of the material is improved, and the good hole transmission characteristic of the material is finally realized. The material has good thermal stability, simple synthesis, easily obtained raw materials and solution processing. The hole transport material is applied to perovskite solar cells, and has good hole transport characteristics, excellent stability and excellent material performance. The imide structure can further passivate a perovskite layer, so that the stability of the battery can be effectively improved while high photoelectric conversion efficiency is realized. The hole transport material based on the invention can obtain high photoelectric conversion efficiency without doping, has obvious advantage in stability compared with the current commonly used hole transport material Spiro-OMeTAD, has the potential of replacing the current hole transport material, and has good industrialization prospect.

Claims (6)

1. An imide compound having a formula as shown in formula (I):
Figure FDA0003889149100000011
R 1 selected from C1-C30 alkyl;
R 2 selected from hydrogen, fluorine atoms, straight chain or branched chain alkyl of C1-C18, methoxy, methylthio;
the Ar structural unit is selected from any one of the following structural units:
Figure FDA0003889149100000012
2. the imide compound according to claim 1, wherein the imide compound is:
Figure FDA0003889149100000013
Figure FDA0003889149100000021
3. the method for producing the imide compound according to claim 1, wherein the specific synthetic route is as follows:
Figure FDA0003889149100000031
R 1 、R 2 ar is as defined in claim 1.
4. Use of the imide compound according to any one of claims 1 to 2 as a hole transport material.
5. A perovskite solar cell device, characterized in that at least one functional layer of the perovskite solar cell device contains the imide compound according to any one of claims 1 to 2.
6. The perovskite solar cell device according to claim 5, wherein the functional layer is a hole transport layer.
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