An amine derivative organic compound and application thereof, a perovskite solar cell

Abstract

The application relates to the technical field of solar cells, and discloses an amine derivative organic compound and application thereof and a perovskite solar cell. The compound contains a structure shown in ring A, and any bondable position in a structure shown in ring B is connected with any bondable position in the structure shown in the ring A through an optional L1 connecting group; and any bondable position in a structure shown in ring C is connected with any bondable position in the structure shown in the ring A through an optional L2 connecting group. The compound provided by the application can effectively extract and transport electrons as an electron transport layer material, is beneficial to the increase of current and a filling factor, has a high photoelectric conversion rate when applied to a perovskite solar cell, and has a good application prospect.

Description

Technical Field

[0001] This invention relates to the field of solar cell technology, specifically to an amine derivative organic compound and its application, and a perovskite solar cell. Background Technology

[0002] The depletion of fossil fuels and their environmental pollution during use make the development of new energy sources an important guarantee for the sustainable development of human civilization, with solar photovoltaic being the most promising solution.

[0003] Among them, all-solid-state organic-inorganic hybrid perovskite solar cells (PSCs) have achieved a maximum photoelectric conversion efficiency of 25.2% in just ten years since their introduction. Their excellent photoelectric conversion efficiency has broad application prospects and has attracted the attention of researchers, thus setting off a research boom in perovskite solar cells.

[0004] A perovskite solar cell consists of a conductive glass substrate, an electron transport layer, a perovskite layer, a hole transport layer, and a metal electrode. The working principle of a perovskite solar cell is as follows: When the perovskite layer absorbs sunlight and is excited, it generates a pair of free electrons and holes. The free electrons excited to the perovskite conduction band diffuse to the perovskite / electron transport layer interface and are injected into the conduction band of the electron transport layer. The electrons then travel through the electron transport layer to the conductive glass electrode, and then flow through the external circuit to the metal electrode. Simultaneously, while free electrons are excited to the perovskite conduction band, holes also travel through the perovskite valence band and diffuse to the perovskite / hole transport layer interface, then are injected into the valence band of the hole transport layer. The holes then travel through the hole transport layer and return to the metal electrode, where they recombine with the free electrons to form a complete circuit.

[0005] Inverted perovskite solar cells have attracted widespread attention due to their advantages such as good stability, negligible hysteresis, and high matching degree in tandem cells. However, their photoelectric conversion efficiency is still lower than that of conventional structure devices. This is mainly due to the weaker chemical interaction between the electron transport material and the perovskite, and the poorer energy state structure matching, resulting in greater interfacial recombination losses between the electron transport layer and the perovskite layer, thus leading to a lower open-circuit voltage. In recent years, surface modification of the perovskite layer has been proven to be an effective strategy to suppress interfacial recombination losses.

[0006] Therefore, developing a novel electron transport material that is low-cost, high-performance, and capable of improving the photovoltaic performance of devices through perovskite surface reconstruction has significant commercial application value. Summary of the Invention

[0007] The purpose of this invention is to overcome the shortcomings of high production cost and low cell efficiency of electron transport materials in existing perovskite solar cells, and to provide a new type of electron transport material that is low in cost and has superior performance.

[0008] To achieve the above objectives, a first aspect of the present invention provides an amine derivative organic compound containing the structure shown in ring A, wherein any bondable position in the structure shown in ring B is connected to any bondable position in the structure shown in ring A via an optional L1 linking group; and any bondable position in the structure shown in ring C is connected to any bondable position in the structure shown in ring A via an optional L2 linking group.

[0009]

[0010] In ring A, X is either O or S;

[0011] In ring B, R1 and R2 are each independently selected from C with or without heteroatoms. 6-30 The aromatic group; R3 is -(CH2). n -NH2, where n is an integer from 0 to 10;

[0012] In ring C, any two of X1, X2, X3, and X4 are N, and the remaining two are C; and any position in ring C that can be substituted is replaced by an R group, where R is selected from H, C containing or without heteroatoms. 6-30 At least one of the aromatic groups;

[0013] The arbitrarily existing L1 and L2 are each independently C with or without heteroatoms. 6-30 At least one of the aromatic groups.

[0014] A second aspect of the present invention provides the application of the amine derivative organic compounds described in the first aspect in perovskite solar cells.

[0015] A third aspect of the present invention provides a perovskite solar cell comprising one or more of the amine derivative organic compounds described in the first aspect, the perovskite solar cell comprising a conductive glass substrate, a hole transport layer, a perovskite light-absorbing layer, an electron transport layer, a buffer layer, and a metal electrode, wherein the compound is present in the electron transport layer of the perovskite solar cell.

[0016] The compound provided by this invention is introduced into perovskite solar cells as an electron transport layer material to reconstruct the perovskite surface, significantly reducing the interfacial recombination loss between the electron transport layer and the perovskite layer, thereby improving the open-circuit voltage and photoelectric conversion efficiency of the device.

[0017] The present invention has at least the following specific advantages:

[0018] 1. The amine derivative organic compounds provided by this invention have suitable energy levels and are high-performance organic semiconductor materials that can improve the efficiency of perovskite solar cell devices.

[0019] 2. The synthesis method of the amine derivative organic compounds provided by this invention is simple, has a clear structure, low cost, and excellent performance, and has high application value in the optoelectronic field such as solar cells.

[0020] 3. The alkylamines in the amine derivative organic compounds provided by this invention have a strong interaction with the excess lead iodide on the perovskite surface, which enhances the dipole interaction between the electron transport layer / perovskite layer, thereby enhancing electron extraction and transport at the interface. More efficient charge extraction helps to reduce the energy loss caused by carrier recombination at the interface, thereby improving the open-circuit voltage of the device.

[0021] 4. The alkylamines in the amine derivative organic compounds provided by this invention have a strong interaction with lead iodide, which enables the compounds of this invention to build a molecular barrier on the perovskite surface, effectively delaying the migration of iodide ions within the device and improving the stability of the device. Detailed Implementation

[0022] The endpoints and any values ​​of the ranges disclosed herein are not limited to the precise ranges or values, and these ranges or values ​​should be understood to include values ​​close to these ranges or values. For numerical ranges, the endpoint values ​​of the various ranges, the endpoint values ​​of the various ranges and individual point values, and individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be considered as specifically disclosed herein.

[0023] The "C" described in this invention 6-30 "Aromatic group" refers to an aryl group with a total number of carbon atoms of 6-30, including but not limited to phenyl, biphenyl, naphthyl, anthracene, phenanthrene, etc.

[0024] Regarding ring B in this invention, the "○" represents a conjugated structure, which can form double bonds anywhere that a double bond can be formed.

[0025] Spiro-OMeTAD is 2,2',7,7'-tetrakis[N,N-di(4-methoxyphenyl)amino]-9,9'-spirodifluorene, CAS number 207739-72-8;

[0026] PEDOT:PSS is poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid), CAS number 155090-83-8;

[0027] PTAA is poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine], CAS number 1333317-99-9;

[0028] BCP is 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, CAS number 4733-39-5.

[0029] As previously described, a first aspect of the present invention provides an amine derivative organic compound containing the structure shown in ring A, wherein any bondable position in the structure shown in ring B is connected to any bondable position in the structure shown in ring A via an optional L1 linking group; and any bondable position in the structure shown in ring C is connected to any bondable position in the structure shown in ring A via an optional L2 linking group.

[0030]

[0031] In ring A, X is either O or S;

[0032] In ring B, R1 and R2 are each independently selected from C with or without heteroatoms. 6-30 The aromatic group; R3 is -(CH2). n -NH2, where n is an integer from 0 to 10;

[0033] In ring C, any two of X1, X2, X3, and X4 are N, and the remaining two are C; and any position in ring C that can be substituted is replaced by an R group, where R is selected from H, C containing or without heteroatoms. 6-30 At least one of the aromatic groups;

[0034] The arbitrarily existing L1 and L2 are each independently C with or without heteroatoms. 6-30 At least one of the aromatic groups.

[0035] Preferably, in ring B, R1 and R2 are each independently selected from any one of phenyl, naphthyl, anthraceneyl, phenanthryl, and biphenyl; R3 is -(CH2). n -NH2, where n is an integer from 0 to 8. More preferably, in ring B, R1 and R2 are the same and selected from any one of phenyl, naphthyl, anthraceneyl, phenanthryl, and biphenyl; R3 is -(CH2). n -NH2, where n is an integer from 0 to 6. More preferably, in ring B, R1 and R2 are the same and selected from any one of phenyl, naphthyl, anthraceneyl, phenanthryl, and biphenyl; R3 is -(CH2). n -NH2, where n is an integer from 0 to 6; and the meta position of the N atom in ring B is connected to any bondable position in the structure shown by ring A through an optional L1 linking group.

[0036] Preferably, in ring C, any two of X1, X2, X3, and X4 are N, and the remaining two are C; and any substituted position in ring C is substituted by an R group, where R is selected from H, C containing or not containing heteroatoms. 6-30 At least one of the aromatic groups. More preferably, in ring C, any two of X1, X2, X3, and X4 are N, and the remaining two are C; and any position in ring C that can be substituted is substituted by an R group, wherein R is selected from at least one of H, phenyl, naphthyl, anthraceneyl, phenanthryl, and biphenyl. Even more preferably, in ring C, X1 and X3 are N, and X2 and X4 are C, or X1 and X2 are N, and X3 and X4 are C; and any position in ring C that can be substituted is substituted by an R group, wherein R is selected from at least one of H, phenyl, naphthyl, anthraceneyl, phenanthryl, and biphenyl.

[0037] Preferably, the optionally present L1 and the optionally present L2 are each independently at least one selected from phenyl, naphthyl, anthraceneyl, phenanthryl, and biphenyl. More preferably, the optionally present L1 and the optionally present L2 are each independently at least one selected from phenyl, naphthyl, and biphenyl.

[0038] According to a preferred embodiment ①:

[0039] In ring A, X is either O or S;

[0040] In ring B, R1 and R2 are each independently selected from any one of phenyl, naphthyl, anthraceneyl, phenanthryl, and biphenyl; R3 is -(CH2). n -NH2, where n is an integer from 0 to 8;

[0041] In ring C, any two of X1, X2, X3, and X4 are N, and the remaining two are C; and any position in ring C that can be substituted is substituted by an R group, wherein R is selected from at least one of H, phenyl, naphthyl, anthraceneyl, phenanthryl, and biphenyl.

[0042] The optional L1 and optional L2 are each independently at least one of phenyl, naphthyl, anthraceneyl, phenanthryl, and biphenyl.

[0043] According to a preferred embodiment ②:

[0044] In ring A, X is either O or S;

[0045] In ring B, R1 and R2 are the same and are selected from any one of phenyl, naphthyl, anthraceneyl, phenanthryl, and biphenyl; R3 is -(CH2). n -NH2, where n is an integer from 0 to 6;

[0046] In ring C, any two of X1, X2, X3, and X4 are N, and the remaining two are C; and any position in ring C that can be substituted is substituted by an R group, wherein R is selected from at least one of H, phenyl, naphthyl, anthraceneyl, phenanthryl, and biphenyl.

[0047] The optional L1 and optional L2 are each independently at least one of phenyl, naphthyl, and biphenyl.

[0048] According to a preferred embodiment ③:

[0049] In ring A, X is either O or S;

[0050] In ring B, R1 and R2 are the same and are selected from any one of phenyl, naphthyl, anthraceneyl, phenanthryl, and biphenyl; R3 is -(CH2). n -NH2, n is an integer from 0 to 6; and the meta position of the N atom in ring B is connected to any position in the structure shown by ring A through an optional L1 linking group;

[0051] In ring C, X1 and X3 are N, and X2 and X4 are C, or X1 and X2 are N, and X3 and X4 are C; and any position in ring C that can be substituted is substituted by an R group, wherein R is selected from at least one of H, phenyl, naphthyl, anthraceneyl, phenanthryl, and biphenyl.

[0052] The optional L1 and optional L2 are each independently at least one of phenyl, naphthyl, and biphenyl.

[0053] According to a particularly preferred embodiment, the compound is any one of the following compounds:

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060] This invention does not impose any particular limitation on the specific methods for preparing the aforementioned compounds. Those skilled in the art can obtain the aforementioned compounds of this invention by combining the specific structural formulas provided by this invention with conventional process routes in the field of organic synthesis. Furthermore, several examples are exemplarily listed below to illustrate the preparation methods of the compounds of this invention. Those skilled in the art can also obtain the specific preparation methods of all other compounds by changing the types of raw materials according to the preparation methods of the compounds described below. This invention will not further describe the preparation methods of all compounds in detail, and this should not be construed as a limitation of the invention.

[0061] As previously stated, a second aspect of the present invention provides the application of the amine derivative organic compounds described in the first aspect in perovskite solar cells.

[0062] As previously described, a third aspect of the present invention provides a perovskite solar cell comprising one or more of the amine derivative organic compounds described in the first aspect, the perovskite solar cell comprising a conductive glass substrate, a hole transport layer, a perovskite light absorption layer, an electron transport layer, a buffer layer, and a metal electrode, wherein the compound is present in the electron transport layer of the perovskite solar cell.

[0063] The perovskite solar cell described in this invention refers to a type of solar cell that uses perovskite-type organometal halide semiconductors as light-absorbing materials.

[0064] Preferably, the perovskite solar cell of the present invention comprises, from bottom to top, a conductive glass substrate, a hole transport layer, a perovskite light absorption layer, an electron transport layer, a buffer layer, and a metal electrode, wherein the compound is present in the electron transport layer of the perovskite solar cell.

[0065] Preferably, the conductive glass substrate includes a conductive layer, and the conductive layer is selected from at least one of an indium tin oxide layer, an aluminum-doped zinc oxide layer, and a fluorine-doped tin oxide layer.

[0066] Preferably, the metal electrode includes a metal cathode, and the material forming the metal cathode is selected from at least one of Al, Ag, Au, Mo and Cr.

[0067] Preferably, the material forming the hole transport layer is an inorganic hole transport material and / or an organic hole transport material. Particularly preferably, the inorganic hole transport material is selected from at least one of NiO, Cu2O, or MoO3. More preferably, the organic hole transport material is selected from at least one of Spiro-OMeTAD, PEDOT:PSS, and PTAA.

[0068] Preferably, the perovskite light-absorbing layer contains at least one perovskite material ABY3; wherein A is NH=CHNH 3+ CH3NH 3+ or Cs + B is Pb 2+ or Sn 2+ ;Y is I - Cl - or Br - .

[0069] This invention does not impose any particular restrictions on the raw materials and preparation methods for the buffer layer. Those skilled in the art can use conventional raw materials and conventional preparation methods to prepare it. This invention will not be described in detail here, and those skilled in the art should not understand it as a limitation of this invention.

[0070] This invention does not impose any particular requirements on the specific fabrication process of the perovskite solar cell. Those skilled in the art can use known fabrication processes for perovskite solar cells. In order to illustrate the beneficial effects of the compound provided by this invention in the presence of perovskite solar cells, the following section of this invention provides an exemplary fabrication process and specific parameters for a perovskite solar cell in the device embodiment section. Those skilled in the art should not understand this as a limitation of the invention.

[0071] The present invention will be described in detail below through examples. In the following examples, unless otherwise specified, all raw materials used are commercially available products. Unless otherwise specified, room temperature as mentioned below refers to 25±1℃.

[0072] Preparation Example 1: Synthesis of Intermediate A

[0073]

[0074] Synthesis of intermediate A: In a 1L three-necked flask under nitrogen protection, 2-amine-4,6-diphenylpyrimidine (81 mmol) was dissolved in N,N-dimethylformamide (DMF, 200 mL), and a saturated N,N-dimethylformamide solution (70 mL) containing N-bromosuccinimide (NBS, 81 mmol) was added dropwise. After the addition was complete, the temperature was raised to 100 °C and stirred for 20 h. HPLC analysis showed that the reaction of the starting material was basically complete. After the reaction solution was cooled to room temperature, water (350 mL) was added dropwise, and the mixture was stirred for 30 min. The mixture was filtered to obtain the crude product, dried, and recrystallized from toluene / ethanol to obtain intermediate A (yield: 58%).

[0075] Mass spectrometry: C16H12BrN3, theoretical value: 325.02, measured value: 325.05. Elemental analysis: theoretical value: C: 58.91; H: 3.71; N: 12.88; measured value: C: 58.95; H: 3.70; N: 12.85.

[0076] Preparation Example 2: Synthesis of Intermediate B

[0077]

[0078] Synthesis of intermediate B-1: In a 500 mL three-necked flask under nitrogen protection, 1,4-dioxane solvent (150 mL), 2-chloro-4,6-diphenylpyrimidine (56.4 mmol), boron pinacol ester (58 mmol), potassium acetate (141 mmol), and [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (0.56 mmol) were added sequentially. The mixture was heated to reflux for 4 h. HPLC analysis confirmed the reaction was complete. After cooling the reaction solution to room temperature, the solution was evaporated under reduced pressure to obtain a crude product. The crude product was dissolved in toluene solvent, heated and stirred, and then heated to reflux. The solution was decolorized by hot silica gel column chromatography. The filtrate was evaporated under reduced pressure to a small amount of solvent remaining. Ethanol (230 mL) was added and the mixture was stirred. Recrystallized from toluene / ethanol to obtain a white solid (yield: 90%).

[0079] Synthesis of intermediate B-2: In a 1L three-necked flask under nitrogen protection, a mixed solution of intermediate B-1 (50.7 mmol), bromoiodine (50.7 mmol), toluene (120 mL), ethanol (80 mL), and water (40 mL) was added sequentially, and stirring was initiated. Then, potassium carbonate (127 mmol) and tetrakis(triphenylphosphine)palladium (0.51 mmol) were added sequentially, and the mixture was heated to reflux for 5 h. HPLC analysis indicated that the reaction was essentially complete. Deionized water (300 mL) was added to the reaction solution, and the mixture was stirred for 10 min. The organic phase was washed three times with water, and the two phases were combined and dried over anhydrous magnesium sulfate. The drying agent was filtered off, the organic solvent was evaporated, and the residue was separated by silica gel column chromatography to obtain intermediate B-2 (yield: 68%).

[0080] Synthesis of intermediate B-3: In a 250 mL three-necked flask under nitrogen protection, intermediate B-2 (32.5 mmol), 28 wt% ammonia (50 mmol), CuI (6.5 mmol, 20 mol%), and ligand 2-quinolinecarboxylic acid-N oxide (16 mmol, 40 mol%) were added, followed by the addition of 100 mL of DMSO. The mixture was stirred at 80 °C for 24 hours, cooled to room temperature, and the reaction mixture was added to 200 mL of water. The mixture was extracted three times with ethyl acetate, and the organic phases were combined, dried over anhydrous magnesium sulfate, and the solvent was evaporated. Column chromatography was used to obtain intermediate B-3 (yield: 87%).

[0081] Synthesis of intermediate B: The synthesis method of intermediate B is the same as that of intermediate A, except that 2-amine-4,6-diphenylpyrimidine is replaced with intermediate B-3 to obtain intermediate B (yield: 62%).

[0082] Mass spectrometry: C17H14BrN3, theoretical value: 339.04, measured value: 339.05. Elemental analysis: theoretical value: C: 60.02; H: 4.15; N: 12.35; measured value: C: 60.01; H: 4.14; N: 12.36.

[0083] Preparation Example 3: Synthesis of Intermediate C

[0084]

[0085] Synthesis of intermediate C-1: The synthesis method of intermediate C-1 is the same as that of intermediate B-2, except that bromoiodomethane is replaced with 1-bromo-2-iodoethane to obtain intermediate C-1 (yield: 64%).

[0086] Synthesis of intermediate C-2: The synthesis method of intermediate C-2 is the same as that of intermediate B-3, except that intermediate B-2 is replaced by intermediate C-1 to obtain intermediate C-2 (yield: 85%).

[0087] Synthesis of intermediate C: The synthesis method of intermediate C is the same as that of intermediate A, except that 2-amine-4,6-diphenylpyrimidine is replaced with intermediate C-2 to obtain intermediate C (yield: 63%).

[0088] Mass spectrometry: C18H16BrN3, theoretical value: 353.05, measured value: 353.06. Elemental analysis: theoretical value: C: 61.03; H: 4.55; N: 11.86; measured value: C: 61.05; H: 4.56; N: 11.89.

[0089] Example 1: Synthesis of Compound 5

[0090]

[0091] Synthesis of intermediate 5-1: In a 500 mL three-necked flask under nitrogen protection, 1,4-dioxane solvent (100 mL), 2-bromo-1,10-phenanthroline (38.6 mmol), boron pinacol ester (40 mmol), potassium acetate (96.5 mmol), and [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (0.39 mmol) were added sequentially. The mixture was heated to reflux for 3 h. HPLC analysis confirmed the reaction was complete. After cooling the reaction solution to room temperature, the solution was evaporated to dryness under reduced pressure to obtain the crude product. The crude product was dissolved in toluene solvent, heated and stirred, and then heated to reflux. The solution was decolorized by hot silica gel column chromatography. The filtrate was evaporated to dryness under reduced pressure until a small amount of solvent remained. Ethanol (150 mL) was added and the mixture was stirred. Recrystallized from toluene / ethanol to obtain intermediate 5-1 (yield: 92%).

[0092] Synthesis of intermediate 5-2: In a 1L three-necked flask under nitrogen protection, a mixed solution of intermediate 5-1 (35.5 mmol), 1-bromo-4-chlorodibenzofuran (35.5 mmol), toluene (70 mL), ethanol (40 mL), and water (20 mL) was added sequentially, and stirring was initiated. Then, potassium carbonate (88.8 mmol) and tetrakis(triphenylphosphine)palladium (0.36 mmol) were added sequentially, and the mixture was heated to reflux for 4 h. HPLC analysis indicated that the reaction was essentially complete. Deionized water (180 mL) was added to the reaction solution, and the mixture was stirred for 10 min. The organic phase was washed three times with water, and the two phases were combined and dried over anhydrous magnesium sulfate. The drying agent was filtered off, the organic solvent was evaporated, and the residue was separated by silica gel column chromatography to obtain intermediate 5-2 (yield: 67%).

[0093] Synthesis of intermediate 5-3: The synthesis method is the same as that of intermediate 5-2, except that intermediate 5-1 and 1-bromo-4-chlorodibenzofuran are replaced with p-chlorophenylboronic acid and intermediate 5-2 to obtain intermediate 5-3 (yield: 72%).

[0094] Synthesis of intermediate 5-4: The synthesis method is the same as that of intermediate 5-1, except that 2-bromo-1,10-phenanthroline is replaced with intermediate 5-3 to obtain intermediate 5-4 (yield: 89%).

[0095] Synthesis of compound 5: The synthesis method is the same as that of intermediate 5-2, except that intermediates 5-1 and 1-bromo-4-chlorodibenzofuran are replaced with intermediates 5-4 and intermediate A to obtain compound 5 (yield: 69%).

[0096] Mass spectrometry: C46H29N5O, theoretical value: 667.24, measured value: 667.25. 1H-NMR (400MHz, CDCl3) (ppm) δ=1.99~2.01 (2H, s), 7.23~7.28 (4H, m), 7.30~7.43 (3H, m), 7.45~7.54 (3H, m), 7.55~7.60 (2H, m), 7.61~7.69 (4H, m), 7.74~7.83 (5H, m), 7.86~7.90 (1H, m), 7.96~8.00 (1H, m), 8.19~8.23 (1H, d), 8.37~8.48 (2H, m), 8.78~8.82 (1H, m).

[0097] Example 2: Synthesis of Compound 6

[0098]

[0099] Synthesis of compound 6: The synthesis method is the same as that of intermediate 5-2, except that intermediates 5-1 and 1-bromo-4-chlorodibenzofuran are replaced with intermediates 5-4 and intermediate B to obtain compound 6 (yield: 65%).

[0100] Mass spectrometry: C47H31N5O, theoretical value: 681.25, measured value: 681.30. 1H-NMR (400MHz, CDCl3) (ppm) δ=1.73~1.70(2H, s), 2.70~2.74(2H, s), 7.23~7.26(4H, s), 7.27~7.43(3H, m), 7.45~7.60(5H, m), 7.61~7.69(4H, m), 7.74~7.83(5H, m), 7.86~7.90(1H, m), 7.96~8.00(1H, m), 8.19~8.23(1H, d), 8.37~8.48(2H, m), 8.78~8.82(1H, m).

[0101] Example 3: Synthesis of Compound 7

[0102]

[0103] Synthesis of compound 7: The synthesis method is the same as that of intermediate 5-2, except that intermediates 5-1 and 1-bromo-4-chlorodibenzofuran are replaced with intermediates 5-4 and intermediate C to obtain compound 7 (yield: 68%).

[0104] Mass spectrometry: C47H33N5O, theoretical value: 695.27, measured value: 695.30. 1H-NMR (400MHz, CDCl3) (ppm) δ=1.22~1.25 (2H, s), 2.64~2.72 (2H, m), 3.02~3.10 (2H, m), 7.23~7.28 (4H, m), 7.30~7.37 (2H, m), 7.38~7.50 (2H, m), 7.51~7.69 (8H, m), 7.74~7.83 (5H, m), 7.86~8.00 (2H, m), 8.19~8.23 (1H, d), 8.37~8.48 (2H, m), 8.78~8.82 (1H, m).

[0105] Example 4: Synthesis of Compound 10

[0106]

[0107] Synthesis of intermediate 10-1: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran is replaced with 1,4-dichlorobenzene to obtain intermediate 10-1 (yield: 56%).

[0108] Synthesis of intermediate 10-2: The synthesis method is the same as that of intermediate 5-1, except that 2-bromo-1,10-phenanthroline is used to replace intermediate 10-1 to obtain intermediate 10-2 (yield: 94%).

[0109] Synthesis of intermediate 10-3: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran and intermediate 5-1 are replaced with 1-bromo-4-iododibenzo[b,d]furan and intermediate 10-2 to obtain intermediate 10-3 (yield: 61%).

[0110] Synthesis of intermediate 10-4: The synthesis method is the same as that of intermediate 5-1, except that 2-bromo-1,10-phenanthroline is used to replace intermediate 10-3 to obtain intermediate 10-4 (yield: 91%).

[0111] Synthesis of compound 10: The synthesis method is the same as that of intermediate 5-2, except that intermediates 5-1 and 1-bromo-4-chlorodibenzofuran are replaced with intermediates 10-4 and intermediate B to obtain compound 10 (yield: 67%).

[0112] Mass spectrometry: C22H12ClN3O, theoretical value: 369.07, measured value: 369.05. 1H-NMR (400MHz, CDCl3) (ppm) δ=1.69~1.73 (2H, s), 2.70~2.74 (2H, s), 7.22~7.29 (2H, m), 7.30~7.43 (3H, m), 7.45~7.57 (4H, m), 7.58~7.70 (5H, m), 7.73~7.91 (7H, m), 7.96~8.01 (1H, m), 8.36~8.48 (2H, m), 8.66~8.72 (2H, m), 8.78~8.83 (1H, m).

[0113] Example 5: Synthesis of Compound 22

[0114]

[0115] Synthesis of intermediate 22-1: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran and intermediate 5-1 are replaced with intermediate B and 4-chlorophenylboronic acid to obtain intermediate 22-1 (yield: 72%).

[0116] Synthesis of intermediate 22-2: The synthesis method is the same as that of intermediate 5-1, except that 2-bromo-1,10-phenanthroline is used to replace intermediate 22-1 to obtain intermediate 22-2 (yield: 94%).

[0117] Synthesis of intermediate 22-3: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran and intermediate 5-1 are replaced with 1-bromo-3-chlorodibenzo[b,d]furan and intermediate 22-2 to obtain intermediate 22-3 (yield: 64%).

[0118] Synthesis of compound 22: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran is replaced with intermediate 22-3 to obtain compound 22 (yield: 70%).

[0119] Mass spectrometry: C47H31N5O, theoretical value: 681.25, measured value: 681.10. ¹H-NMR (400MHz, CDCl3) (ppm) δ=1.65~1.67(2H, s), 2.71~2.73(2H, s), 7.23~7.27(4H, m), 7.27~7.43(3H, m), 7.45~7.54 (3H, m), 7.54~7.60 (2H, m), 7.61~7.69 (4H, m), 7.77~7.83 (4H, m), 7.86~7.90 (1H , m), 7.96~8.00(1H,m), 8.14~8.17(1H,d), 8.37~8.50(3H,m), 8.78~8.82(1H,m).

[0120] Example 6: Synthesis of Compound 51

[0121]

[0122] Synthesis of intermediate 51-1: The synthesis method is the same as that of intermediate 5-1, except that 2-bromo-1,10-phenanthroline is replaced with 2-bromobenzo[h]quinazoline to obtain intermediate 51-1 (yield: 91%).

[0123] Synthesis of intermediate 51-2: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran and intermediate 5-1 are replaced with 1-bromo-4-iododibenzo[b,d]furan and intermediate 51-1 to obtain intermediate 51-2 (yield: 69%).

[0124] Synthesis of intermediate 51-3: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran and intermediate 5-1 are replaced with intermediate 51-2 and 4-chlorophenylboronic acid to obtain intermediate 51-3 (yield: 66%).

[0125] Synthesis of intermediate 51-4: The synthesis method is the same as that of intermediate 5-1, except that 2-bromo-1,10-phenanthroline is used to replace intermediate 51-3 to obtain intermediate 51-4 (yield: 94%).

[0126] Synthesis of compound 51: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran and intermediate 5-1 are replaced with intermediate 51-4 and intermediate C to obtain intermediate 51 (yield: 67%).

[0127] Mass spectrometry: C48H33N5O, theoretical value: 695.27, measured value: 695.30. 1H-NMR (400MHz, CDCl3) (ppm) δ=1.22~1.25 (2H, s), 2.64~2.72 (2H, m), 3.02~3.10 (2H, m), 7.24~7.26 (4H, s), 7.27~7.43 (2H, m), 7.45~7.57 (3H, m), 7.61~7.70 (5H, m), 7.71~7.88 (8H, m), 7.96~8.05 (2H, m), 8.09~8.14 (1H, m), 8.49~8.53 (1H, m), 9.70~9.72 (1H, d).

[0128] Example 7: Synthesis of Compound 63

[0129]

[0130] Synthesis of intermediate 63-1: The synthesis method is the same as that of intermediate 5-1, except that 2-bromo-1,10-phenanthroline is replaced with 2-bromo-9-phenyl-1,10-phenanthroline to obtain intermediate 63-1 (yield: 87%).

[0131] Synthesis of intermediate 63-2: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran and intermediate 5-1 are replaced with 1-bromo-4-iododibenzo[b,d]furan and intermediate 63-1 to obtain intermediate 63-2 (yield: 73%).

[0132] Synthesis of intermediate 63-3: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran and intermediate 5-1 are replaced with intermediate 63-2 and 4-chlorophenylboronic acid to obtain intermediate 63-3 (yield: 70%).

[0133] Synthesis of intermediate 63-4: The synthesis method is the same as that of intermediate 5-1, except that 2-bromo-1,10-phenanthroline is used to replace intermediate 63-3 to obtain intermediate 63-4 (yield: 93%).

[0134] Synthesis of compound 63: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran and intermediate 5-1 are replaced with intermediate 63-4 and intermediate B to obtain intermediate 63 (yield: 71%).

[0135] Mass spectrometry: C53H35N5O, theoretical value: 757.28, measured value: 757.30. 1H-NMR (400MHz, CDCl3) (ppm) δ=1.70~1.73(2H, s), 2.71~2.74(2H, m), 7.23~7.26(4H, m), 7.27~7.43(4H, s), 7.44~7.69(11H, m), 7.74~7.83(5H, m), 7.86~7.91(1H, m), 7.96~8.00(1H, m), 8.19~8.23(1H, m), 8.30~8.36(2H, m), 8.36~8.42(2H, m).

[0136] Example 8: Synthesis of Compound 74

[0137]

[0138] Synthesis of intermediate 74-1: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran is replaced with 1-bromo-4-iododibenzo[b,d]thiophene to obtain intermediate 74-1 (yield: 68%).

[0139] Synthesis of intermediate 74-2: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran and intermediate 5-1 are replaced with intermediate 74-1 and 4-chlorophenylboronic acid to obtain intermediate 74-2 (yield: 65%).

[0140] Synthesis of intermediate 74-3: The synthesis method is the same as that of intermediate 5-1, except that 2-bromo-1,10-phenanthroline is used to replace intermediate 74-2 to obtain intermediate 74-3 (yield: 87%).

[0141] Synthesis of compound 74: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran and intermediate 5-1 are replaced with intermediate 74-3 and intermediate B to obtain intermediate 74 (yield: 64%).

[0142] Mass spectrometry: C47H31N5S, theoretical value: 697.23, measured value: 697.25. 1H-NMR (400MHz, CDCl3) (ppm) δ=1.65~1.67 (2H, s), 2.71~2.73 (2H, s), 7.23~7.27 (4H, s), 7.27~7.36 (2H, m), 7.45~7.57 (4H, m), 7.58~7.69 (5H, m), 7.77~7.90 (7H, m), 8.21~8.25 (1H, d), 8.37~8.48 (3H, m), 8.78~8.82 (1H, m).

[0143] Example 9: Synthesis of Compound 78

[0144]

[0145] Synthesis of intermediate 78-1: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran is replaced with 2-bromo-4-iododibenzo[b,d]thiophene to obtain intermediate 78-1 (yield: 69%).

[0146] Synthesis of intermediate 78-2: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran and intermediate 5-1 are replaced with intermediate 78-1 and 4-chlorophenylboronic acid to obtain intermediate 78-2 (yield: 63%).

[0147] Synthesis of intermediate 78-3: The synthesis method is the same as that of intermediate 5-1, except that 2-bromo-1,10-phenanthroline is used to replace intermediate 78-2 to obtain intermediate 78-3 (yield: 85%).

[0148] Synthesis of compound 78: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran and intermediate 5-1 are replaced with intermediate 78-3 and intermediate B to obtain intermediate 78 (yield: 69%).

[0149] Mass spectrometry: C47H31N5S, theoretical value: 697.23, measured value: 697.25. 1H-NMR (400MHz, CDCl3) (ppm) δ=1.66~1.68 (2H, s), 2.70~2.73 (2H, s), 7.24~7.26 (4H, s), 7.27~7.36 (2H, m), 7.45~7.69 (9H, m), 7.77~7.90 (6H, m), 8.37~8.54 (5H, m), 8.78~8.82 (1H, m).

[0150] Example 10: Synthesis of Compound 94

[0151]

[0152] Synthesis of intermediate 94-1: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran and intermediate 5-1 are replaced with 1-bromo-4-iododibenzo[b,d]thiophene and intermediate 51-1 to obtain intermediate 94-1 (yield: 64%).

[0153] Synthesis of intermediate 94-2: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran and intermediate 5-1 are replaced with intermediate 94-1 and 4-chlorophenylboronic acid to obtain intermediate 94-2 (yield: 69%).

[0154] Synthesis of intermediate 94-3: The synthesis method is the same as that of intermediate 5-1, except that 2-bromo-1,10-phenanthroline is used to replace intermediate 94-2 to obtain intermediate 94-3 (yield: 87%).

[0155] Synthesis of compound 94: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran and intermediate 5-1 are replaced with intermediate 94-3 and intermediate B to obtain intermediate 94 (yield: 76%).

[0156] Mass spectrometry: C47H31N5S, theoretical value: 697.23, measured value: 697.25. 1H-NMR (400MHz, CDCl3) (ppm) δ=1.73~1.75(2H, s), 2.71~2.73(2H, s), 7.24~7.35(5H, m), 7.45~7.57(3H, m), 7.58~7.73(6H, m), 7.75~7.89(8H, m), 8.01~8.14(2H, m), 8.43~8.53(2H, m), 9.70~9.72(1H, d).

[0157] Example 11: Synthesis of Compound 112

[0158]

[0159] Synthesis of intermediate 112-1: The synthesis method is the same as that of intermediate 5-1, except that 2-bromo-1,10-phenanthroline is replaced with 2-bromo-4-phenylbenzo[h]quinazoline to obtain intermediate 112-1 (yield: 90%).

[0160] Synthesis of intermediate 112-2: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran and intermediate 5-1 are replaced with 1-bromo-3-iododibenzo[b,d]thiophene and intermediate 112-1 to obtain intermediate 112-2 (yield: 68%).

[0161] Synthesis of intermediate 112-3: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran and intermediate 5-1 are replaced with intermediate 112-2 and 4-chlorophenylboronic acid to obtain intermediate 112-3 (yield: 71%).

[0162] Synthesis of intermediate 112-4: The synthesis method is the same as that of intermediate 5-1, except that 2-bromo-1,10-phenanthroline is used to replace intermediate 112-3 to obtain intermediate 112-4 (yield: 90%).

[0163] Synthesis of compound 112: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran and intermediate 5-1 are replaced with intermediate 112-4 and intermediate C to obtain intermediate 112 (yield: 72%).

[0164] Mass spectrometry: C54H37N5S, theoretical value: 787.28, measured value: 787.30. 1H-NMR (400MHz, CDCl3) (ppm) δ=1.23~1.26 (2H, s), 2.64~2.72 (2H, m), 3.02~3.09 (2H, m), 7.23~7.35 (5H, m), 7.45~7.57 (4H, m), 7.61~7.73 (8H, m), 7.77~7.88 (8H, m), 8.04~8.15 (3H, m), 8.42~8.53 (2H, m), 8.68~8.70 (1H, d).

[0165] Example 12: Synthesis of Compound 121

[0166]

[0167] Synthesis of intermediate 121-1: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran is replaced with 1-iodo-4-bromodibenzo[b,d]furan to obtain intermediate 121-1 (yield: 71%).

[0168] Synthesis of intermediate 121-2: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran and intermediate 5-1 are replaced with intermediate 121-1 and 4-chlorophenylboronic acid to obtain intermediate 121-2 (yield: 67%).

[0169] Synthesis of intermediate 121-3: The synthesis method is the same as that of intermediate 5-1, except that 2-bromo-1,10-phenanthroline is used to replace intermediate 121-2 to obtain intermediate 121-3 (yield: 88%).

[0170] Synthesis of compound 121: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran and intermediate 5-1 are replaced with intermediate 121-3 and intermediate C to obtain intermediate 121 (yield: 66%).

[0171] Mass spectrometry: C48H33N5O, theoretical value: 695.27, measured value: 695.30. 1H-NMR (400MHz, CDCl3) (ppm) δ=1.22~1.24 (2H, s), 2.64~2.72 (2H, m), 3.02~3.09 (2H, m), 7.23~7.26 (4H, s), 7.27~7.69 (13H, m), 7.77~7.84 (5H, m), 7.86~7.90 (1H, m), 7.96~8.00 (1H, m), 8.13~8.17 (1H, m), 8.37~8.47 (2H, m), 8.78~8.82 (1H, m).

[0172] Example 13: Synthesis of Compound 152

[0173]

[0174] Synthesis of intermediate 152-1: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran and intermediate 5-1 are replaced with intermediate 112-1 and 4-chlorophenylboronic acid to obtain intermediate 152-2 (yield: 65%).

[0175] Synthesis of intermediate 152-2: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran and intermediate 5-1 are replaced with 1-iodo-4-bromodibenzo[b,d]furan and intermediate 152-1 to obtain intermediate 152-2 (yield: 67%).

[0176] Synthesis of intermediate 152-3: The synthesis method is the same as that of intermediate 5-1, except that 2-bromo-1,10-phenanthroline is used to replace intermediate 152-2 to obtain intermediate 152-3 (yield: 94%).

[0177] Synthesis of compound 152: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran and intermediate 5-1 are replaced with intermediate 152-3 and intermediate B to obtain intermediate 152 (yield: 61%).

[0178] Mass spectrometry: C53H35N5O, theoretical value: 757.28, measured value: 757.30. 1H-NMR (400MHz, CDCl3) (ppm) δ=1.74~1.77 (2H, s), 2.70~2.74 (2H, s), 7.22~7.28 (2H, m), 7.30~7.43 (2H, m), 7.45~7.57 (4H, m), 7.61~7.71 (7H, m), 7.72~7.87 (10H, m), 7.93~8.05 (4H, m), 8.08~8.14 (1H, m), 8.48~8.54 (1H, m).

[0179] Example 14: Synthesis of Compound 157

[0180]

[0181] Synthesis of intermediate 157-1: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran is replaced with 1-iodo-4-bromodibenzo[b,d]thiophene to obtain intermediate 157-1 (yield: 63%).

[0182] Synthesis of intermediate 157-2: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran and intermediate 5-1 are replaced with intermediate 157-1 and 4-chlorophenylboronic acid to obtain intermediate 157-2 (yield: 66%).

[0183] Synthesis of intermediate 157-3: The synthesis method is the same as that of intermediate 5-1, except that 2-bromo-1,10-phenanthroline is used to replace intermediate 157-2 to obtain intermediate 157-3 (yield: 89%).

[0184] Synthesis of compound 157: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran and intermediate 5-1 are replaced with intermediate 157-3 and intermediate A to obtain intermediate 157 (yield: 64%).

[0185] Mass spectrometry: C46H29N5S, theoretical value: 683.21, measured value: 683.20. 1H-NMR (400MHz, CDCl3) (ppm) δ=1.99~2.01(2H, s), 7.23~7.26(4H, s), 7.27~7.36(2H, m), 7.45~7.69(9H, m), 7.77~7.90(7H, m), 8.23~8.27(1H, m), 8.37~8.48(3H, m), 8.78~8.82(1H, m).

[0186] Example 15: Synthesis of Compound 182

[0187]

[0188] Synthesis of intermediate 182-1: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran is replaced with 3,7-dibromodibenzo[b,d]furan to obtain intermediate 182-1 (yield: 52%).

[0189] Synthesis of intermediate 182-2: The synthesis method is the same as that of intermediate 5-1, except that 2-bromo-1,10-phenanthroline is used to replace intermediate 182-1 to obtain intermediate 182-2 (yield: 94%).

[0190] Synthesis of compound 182: The synthesis method is the same as that of intermediate 5-2, except that 1-bromo-4-chlorodibenzofuran and intermediate 5-1 are replaced with intermediate 182-2 and intermediate A to obtain intermediate 182 (yield: 68%).

[0191] Mass spectrometry: C41H27N5O, theoretical value: 605.22, measured value: 605.20. 1H-NMR (400MHz, CDCl3) (ppm) δ=1.68~1.71 (2H, s), 2.70~2.74 (2H, s), 7.32~7.37 (1H, d), 7.45~7.70 (9H, m), 7.75~7.84 (6H, m), 7.86~7.91 (2H, m), 7.93~7.99 (1H, m), 8.29~8.31 (1H, d), 8.36~8.48 (2H, m), 8.77~8.83 (1H, m).

[0192] Device Example 1

[0193] The indium tin oxide (ITO) conductive glass was ultrasonically cleaned for 15 minutes each with deionized water, acetone and isopropanol, and then dried in a drying oven at 75°C for later use. The dried ITO glass substrate was then treated in an ozone generator for 10 minutes to remove organic impurities from its surface.

[0194] PTAA was dissolved in chlorobenzene to prepare a solution with a concentration of 2 mg / mL. The solution was then spin-coated onto ITO at 4000 rpm for 30 s and annealed at 100 °C for 10 min to prepare a hole transport layer.

[0195] 1083.12 mg lead iodide and 357.75 mg methyl iodide solid were dissolved in 1 mL of N,N-dimethylformamide (DMF) and stirred at room temperature until completely dissolved to obtain a perovskite precursor solution.

[0196] Before preparing the perovskite layer, the surface of the PTAA film was rinsed with DMF solution. The prepared perovskite precursor solution was spin-coated on the hole transport layer at 5000 rpm for 25 s. 200 μL of anisole antisolvent was added dropwise within 10 s. The perovskite layer was then annealed at 100 °C for 30 min.

[0197] Compound 5, an electron transport material for the device, was vacuum-deposited on top of the light-emitting layer at a deposition rate of 0.1 nm / s and a thickness of 30 nm.

[0198] BCP was dissolved in isopropanol to prepare a solution with a total concentration of 0.5 mg / mL. The solution was then spin-coated at 6000 rpm for 30 s and annealed at 80 °C for 10 min to prepare the BCP layer.

[0199] In 2×10 -4 A 100 nm silver electrode was deposited under Pa conditions to complete the fabrication of a perovskite solar cell.

[0200] The remaining device embodiments of the present invention were prepared using a method similar to that of device embodiment 1, except that compound 5 in device embodiment 1 was replaced with the corresponding compound in Table 1.

[0201] Device Comparison Example 1

[0202] The comparative device was prepared using a method similar to that of Device Example 1, except that compound 5 in Device Example 1 was replaced with compound Ref-1.

[0203]

[0204] Test case

[0205] The device's current density–voltage curves (J–V curves) were obtained from a source meter (Keithley 2400) on an ABET Sun 3000 solar simulator at AM1.5G (100mW cm⁻¹). –2 Obtained under illumination, the battery area is 0.08 cm². 2Before testing, the light intensity was calibrated using a standard silicon cell, the scanning rate was 10mV / s, and the scanning direction was forward and reverse scanning.

[0206] The photovoltaic parameters of each device embodiment and device comparison example are shown in Table 1.

[0207] Table 1

[0208]

[0209]

[0210] In summary, the compounds provided by this invention, as electron transport layer materials, can effectively extract and transport electrons, which is beneficial to improving current and fill factor. When applied to perovskite solar cells, they exhibit high photoelectric conversion efficiency and have good application prospects.

[0211] The preferred embodiments of the present invention have been described in detail above; however, the present invention is not limited thereto. Within the scope of the inventive concept, various simple modifications can be made to the technical solutions of the present invention, including combinations of various technical features in any other suitable manner. These simple modifications and combinations should also be considered as the content disclosed in the present invention and are all within the protection scope of the present invention.

Claims

1. An amine derivative organic compound, characterized in that, The compound contains the structure shown in ring A, and the structure shown in ring B contains... The positions shown are connected to any bondable position in the structure shown by ring A via optional L1 linking groups; and any bondable position in the structure shown by ring C. The position shown is connected to any position in the structure shown by ring A via an optional L2 linking group; Ring A: Ring B: Ring C: In ring A, X is either O or S; In ring B, R1 and R2 are each independently selected from C with or without heteroatoms. 6-30 The aromatic group; R3 is -(CH2). n -NH2, where n is an integer from 0 to 10; In ring C, any two of X1, X2, X3, and X4 are N, and the remaining two are C; and any substituted position in ring C is substituted by an R group, where R is selected from H, C with or without heteroatoms. 6-30 At least one of the aromatic groups; The arbitrarily existing L1 and L2 are each independently C with or without heteroatoms. 6-30 At least one of the aromatic groups.

2. The compound according to claim 1, wherein, In ring A, X is either O or S; In ring B, R1 and R2 are each independently selected from any one of phenyl, naphthyl, anthraceneyl, phenanthryl, and biphenyl; R3 is -(CH2). n -NH2, where n is an integer from 0 to 8; In ring C, any two of X1, X2, X3, and X4 are N, and the remaining two are C; and any position in ring C that can be substituted is substituted by an R group, wherein R is selected from at least one of H, phenyl, naphthyl, anthraceneyl, phenanthryl, and biphenyl. The optional L1 and optional L2 are each independently at least one of phenyl, naphthyl, anthraceneyl, phenanthryl, and biphenyl.

3. The compound according to claim 2, wherein, In ring A, X is either O or S; In ring B, R1 and R2 are the same and are selected from any one of phenyl, naphthyl, anthraceneyl, phenanthryl, and biphenyl; R3 is -(CH2). n -NH2, where n is an integer from 0 to 6; In ring C, any two of X1, X2, X3, and X4 are N, and the remaining two are C; and any position in ring C that can be substituted is substituted by an R group, wherein R is selected from at least one of H, phenyl, naphthyl, anthraceneyl, phenanthryl, and biphenyl. The optional L1 and optional L2 are each independently at least one of phenyl, naphthyl, and biphenyl.

4. The compound according to claim 3, wherein, In ring A, X is either O or S; In ring B, R1 and R2 are the same and are selected from any one of phenyl, naphthyl, anthraceneyl, phenanthryl, and biphenyl; R3 is -(CH2). n -NH2, n is an integer from 0 to 6; and the meta position of the N atom in ring B is connected to any position in the structure shown by ring A through an optional L1 linking group; In ring C, X1 and X3 are N, and X2 and X4 are C, or X1 and X2 are N, and X3 and X4 are C; and any position in ring C that can be substituted is substituted by an R group, wherein R is selected from at least one of H, phenyl, naphthyl, anthraceneyl, phenanthryl, and biphenyl. The optional L1 and optional L2 are each independently at least one of phenyl, naphthyl, and biphenyl.

5. The compound according to claim 4, wherein, The compound is any one of the following compounds: 。 6. The use of the amine derivative organic compound according to any one of claims 1-5 in perovskite solar cells.

7. A perovskite solar cell containing one or more compounds of the amine derivative organic compounds according to any one of claims 1-5, characterized in that, The perovskite solar cell includes a conductive glass substrate, a hole transport layer, a perovskite light-absorbing layer, an electron transport layer, a buffer layer, and a metal electrode, wherein the compound is present in the electron transport layer of the perovskite solar cell.

8. The perovskite solar cell according to claim 7, wherein, The metal electrode includes a metal cathode, and the material forming the metal cathode is selected from at least one of Al, Ag, Au, Mo and Cr.

9. The perovskite solar cell according to claim 7 or 8, wherein, The material forming the hole transport layer is an inorganic hole transport material and / or an organic hole transport material.

10. The perovskite solar cell according to claim 9, wherein, The inorganic hole transport material is selected from at least one of NiO, Cu2O or MoO3.

11. The perovskite solar cell according to claim 9, wherein, The organic hole transport material is selected from at least one of Spiro-OMeTAD, PEDOT:PSS, and PTAA.

12. The perovskite solar cell according to claim 7 or 8, wherein, The perovskite light-absorbing layer contains at least one perovskite material ABY3; wherein, A is NH=CHNH 3+ CH3NH 3+ or Cs + B is Pb 2+ or Sn 2+ ;Y is I - Cl - or Br - .

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