Organic compound, and preparation method therefor and use thereof

Abstract

An organic compound as represented by formula 1, and a preparation method therefor and the use thereof. The organic compound comprises decacyclene triimide (DTI) as a parent structure, and has three terminal substituents respectively linked to three N terminals of the parent structure. The organic compound has a relatively large steric hindrance and a relatively large conjugate plane, which enables electrons to have a relatively high mobility, thereby effectively improving electron transport. The terminal substituents can regulate the interface energy level, increase the solubility of the organic compound in an organic solvent, and effectively improve the film-forming performance of an electron transport layer. Therefore, the organic compound, as an electron transport material, can promote charge transfer and improve the stability of an electronic device.

Description

Organic compound, and preparation method and application thereof

[0001] The present application claims priority to the Chinese patent application No. 202410896125.0 filed on July 5, 2024, and titled "Organic compound, and preparation method and application thereof", the content of which is incorporated herein by reference in its entirety. TECHNICAL FIELD

[0002] The present application relates to the technical field of organic electroluminescent materials, in particular to an organic compound, and a preparation method and application thereof, and the application mainly refers to the application of the organic compound in the field of electron transport materials, electronic elements or electronic devices. BACKGROUND

[0003] Perovskite solar cells (PSCs) have attracted extensive attention in recent years as a high-efficiency, low-cost alternative to traditional solar energy conversion. In transverse perovskite solar cells, the electron transport layer plays an important role in extracting and transporting carriers, blocking holes, adjusting the interface energy level structure, and inhibiting charge recombination. Currently, fullerenes and their derivatives are commonly used as organic electron transport materials, but their synthesis is relatively difficult and requires 6-7 steps, resulting in high synthesis cost. Fullerenes and their derivatives also have the problems of difficulty in modification, poor solubility, single energy level adjustability, poor air stability, and poor film forming performance, which leads to poor device performance.

[0004] Therefore, there is an urgent need to develop an organic compound that can be used as an electron transport layer material. The organic compound not only needs to have a low cost, but also needs to improve the film forming performance of the electron transport layer and promote charge transfer in order to improve the stability of the electronic device.

[0005] SUMMARY

[0006] The present application provides an organic compound, and a preparation method and application thereof to solve or alleviate the technical problems proposed above. The organic compound provided by the present application can effectively improve the film forming performance of the electron transport layer, improve electron transport, promote charge transfer, and thus improve the stability of the device.

[0007] In a first aspect, the present application provides an organic compound, and the structure of the organic compound is shown in formula 1:

[0008] wherein R is

[0009] L1 is selected from substituted or unsubstituted alkylene with 1-5 carbon atoms;

[0010] Ar1, Ar2 are the same or different, each independently selected from hydrogen, a substituted or unsubstituted alkyl group having 1-50 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1-50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-50 carbon atoms, a substituted or unsubstituted aryl group having 6-50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3-50 carbon atoms; or Ar1, Ar2 together with the carbon atom to which they are attached form a cyclic structure;

[0011] In Ar1 and Ar2, the heteroatom in the heteroalkyl group is selected from N, O, S, Si;

[0012] In Ar1 and Ar2, the heteroatom in the heteroaryl group is selected from N, O, S, Si;

[0013] The substituents in L1, Ar1 and Ar2 are the same or different, each independently selected from a halogen group, a nitro group, a cyano group, a mercapto group.

[0014] In a second aspect, the embodiments of the present application provide a preparation method of any of the above organic compounds, comprising:

[0015] Decacyclene is used as raw material A to perform an amino acylation reaction with 1-piperidine carbonyl chloride to obtain an intermediate product B,

[0016] The intermediate product B is subjected to a hydrolysis reaction with hydrobromic acid to obtain an intermediate product C,

[0017] The intermediate product C is subjected to a condensation reaction with a primary amine to obtain a final product D,

[0018] In a third aspect, the embodiments of the present application provide an electron transport material comprising any of the above organic compounds.

[0019] In a fourth aspect, the embodiments of the present application provide an electronic element, characterized in comprising an anode and a cathode arranged oppositely, and a functional layer arranged between the anode and the cathode; the functional layer comprises any of the above organic compounds.

[0020] In a fifth aspect, the embodiments of the present application provide an electronic device comprising any of the above electronic elements.

[0021] The embodiments of the present application can include the following advantages by adopting the above technical solutions:

[0022] The organic compound provided by the embodiment of the present application takes decacyclene triimide (DTI) as a mother nucleus, and has three terminal substituents connected to three N terminals of the mother nucleus respectively; the three-dimensional core structure of the decacyclene triimide mother nucleus can increase steric hindrance, effectively inhibit excessive aggregation of molecules, and meanwhile maintain high electron mobility; through modification of the terminal substituents of the mother nucleus, the terminal substituents make the decacyclene triimide mother nucleus have a larger conjugated plane, so that the decacyclene triimide mother nucleus has a more matched LUMO energy level, and the degree of π-extension can be effectively improved to improve electron transport; the terminal substituents can also regulate the interface energy level, increase the solubility of the organic compound in an organic solvent, effectively improve the film forming performance of the electron transport layer, facilitate the formation of a uniform and dense electron transport layer, promote charge transfer, and improve the stability of the device. BRIEF DESCRIPTION OF DRAWINGS

[0023] The drawings accompanying the present application are not necessarily drawn to scale. It is to be understood that these drawings only depict some embodiments in accordance with the disclosure and should not be considered to be limiting of the scope of the disclosure.

[0024] FIG. 1 is a structural schematic diagram of a perovskite solar cell provided by the embodiment of the present application.

[0025] Explanation of reference signs:

[0026] 100, anode; 200, cathode; 300, functional layer; 310, hole transport layer; 320, perovskite light absorbing layer; 330, electron transport layer; 340, cathode buffer layer. DETAILED DESCRIPTION

[0027] Embodiments of the present application will now be described more fully with reference to the accompanying drawings, in which examples of embodiments are shown. In the drawings, the size of layers, regions, elements and the relative sizes among them can be exaggerated for clarity. The same or similar reference signs are used throughout the drawings to denote the same or similar elements or elements having the same or similar functions. The embodiments described by reference to the drawings are exemplary only, and are used to explain the present application, and cannot be understood as limiting the present application. It should be noted that the embodiments in the present application and the features in the embodiments can be combined with each other without conflict. The described features, structures or characteristics can be combined in any suitable way in one or more embodiments. In the following description, many specific details are provided to give a full understanding of the embodiments of the present application.

[0028] To facilitate the understanding of the technical solutions provided by the embodiments of the present application by those skilled in the art, the related art is described as follows:

[0029] At present, fullerene and its derivatives commonly used as organic electron transport materials have problems such as high cost, single energy level adjustability, and poor air stability.

[0030] The applicant finds that non-fullerene small molecule material-arylidene diimine derivative has a conjugated planar structure, usually has high thermal stability and chemical stability, and has low synthesis cost, good batch repeatability, and multiple reaction sites for modification, which is expected to replace fullerene as an electron transport material; however, as an electron transport material, non-fullerene small molecule material-arylidene diimine derivative has a strong π-π stacking tendency, which leads to strong molecular aggregation, greatly affects the morphology and transport performance of the film, and thus affects the device performance.

[0031] In view of the above problems, the present application aims to provide an organic compound as an electron transport material, which has a decacyclene triimide (DTI) as a mother nucleus, and has three terminal substituents connected to the N-terminal of the mother nucleus. The DTI is used as the mother nucleus, the terminal substituent modification is performed through molecular structure adjustment, and the synthesis is simple and easy to modify. The three-dimensional core structure of the decacyclene triimide mother nucleus can increase the steric hindrance, effectively inhibit the excessive aggregation of molecules, and maintain high electron mobility; through the modification of the terminal substituent of the mother nucleus, the decacyclene triimide mother nucleus has a larger conjugated plane, so that it has a more matched LUMO energy level, and the electron transport can also be effectively improved by increasing the π-extension degree; the terminal substituent R group can also regulate the interface energy level, increase the solubility of the organic compound in organic solvents, effectively improve the film forming performance of the electron transport layer, facilitate the formation of a uniform and dense electron transport layer, promote charge transfer, and improve the stability of the device.

[0032] In the present application, is a position combined with other substituents or combination positions.

[0033] In the present application, the description method "each of … is independently" can be interchangeable with "… is respectively independently" and "… is independently selected from", and should be interpreted broadly, which can mean that in different groups, the specific options expressed by the same symbols between them do not affect each other, or in the same group, the specific options expressed by the same symbols between them do not affect each other. For example, "the substituents in L1, Ar1 and Ar2 are the same or different, each independently selected from halogen groups, nitro groups, cyano groups, and thiol groups", which means that the substituents in L1 can be the same as or different from the substituents in Ar1 or Ar2; and when there are more than two substituents in L1, the two or more substituents can be the same or different; in short, the options of each substituent do not affect each other.

[0034] In the present application, the term "substituted or unsubstituted" means that the functional group recited after the term can or can not have a substituent (hereinafter, the substituents will be collectively referred to as Rcfor the convenience of description). For example, "substituted or unsubstituted aryl" means aryl having a substituent Rc, or aryl which is not substituted. The substituents Rcmentioned above, for example, can be a halogen group, a nitro group, a cyano group, a mercapto group. In the present application, a "substituted" functional group can be substituted with one or two or more substituents from among the above-mentioned Rc; when two substituents Rcare attached to the same atom, the two substituents Rcmay exist independently. A substituted alkyl group can be an alkyl group in which one or two or more hydrogen atoms are substituted with a group such as a halogen group, a nitro group, a cyano group, a mercapto group. A substituted aryl group can be an aryl group in which one or two or more hydrogen atoms are substituted with a group such as a halogen group, a nitro group, a cyano group, a mercapto group. A substituted heteroaryl group can be a heteroaryl group in which one or two or more hydrogen atoms are substituted with a group such as a halogen group, a nitro group, a cyano group, a mercapto group.

[0035] In the present application, the number of carbon atoms of a substituted or unsubstituted functional group means the total number of carbon atoms. For example, the number of carbon atoms of a substituted aryl group means the total number of carbon atoms of the aryl group and the substituents on the aryl group; the number of carbon atoms of a substituted heteroaryl group means the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group. For example, if L1is selected from an alkylene group having a substituted number of carbon atoms of 5, the total number of carbon atoms of the alkylene group and the substituents thereon is 5; if Ar1is selected from an aryl group having a substituted number of carbon atoms of 20, the total number of carbon atoms of the aryl group and the substituents thereon is 20.

[0036] In the present application, "hetero" means that at least one N, O, S, Si, etc. hetero atom is included in a functional group, and the remaining atoms are carbon and hydrogen, when a specific definition is not otherwise provided.

[0037] In the present application, "alkyl" can include straight-chain alkyl or branched-chain alkyl. The "alkyl" of the present application can have 1 to 50 carbon atoms, in some embodiments, the number of carbon atoms in the alkyl group can be 1 to 30, in some embodiments, the number of carbon atoms in the alkyl group can be 1 to 20, in some other embodiments, the number of carbon atoms in the alkyl group can be 1 to 15, in some other embodiments, the number of carbon atoms in the alkyl group can be 3 to 15, in some other embodiments, the number of carbon atoms in the alkyl group can be 1 to 10. Of course, the number of carbon atoms in the alkyl group can also be other numbers, for example, the number of carbon atoms in the alkyl group can be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 15.

[0038] In the present application, the term "alkylene" means a divalent group formed by further losing one hydrogen atom from an alkyl group.

[0039] In the present application, "alkylene" can have 1 to 5 carbon atoms. In the present application, numerical ranges such as "1 to 5" mean each integer within the given range; for example, "1 to 5 carbon atoms" means that the alkylene group can contain 1 carbon atom, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, or 5 carbon atoms. Specific examples of alkylene groups include, but are not limited to, methylene, ethylene, propylene, isopropylene, n-butylene, isobutylene, sec-butylene, t-butylene, and pentylene.

[0040] In the present application, "heteroalkyl" means an alkyl group in which 1, 2, 3, 4, or 5 carbon atoms are replaced by a heteroatom, which can be at least one of O, N, Si, S. The "heteroalkyl" of the present application can contain 3-50 carbon atoms, in some embodiments the number of carbon atoms in the heteroalkyl group can be 3-30, in other embodiments the number of carbon atoms in the heteroalkyl group can be 3-20, in other embodiments the number of carbon atoms in the heteroalkyl group can be 3-15, in other embodiments the number of carbon atoms in the heteroalkyl group can be 1-10. Of course, the number of carbon atoms in the heteroalkyl group can also be other numbers, for example, the number of carbon atoms in the heteroalkyl group can be 1, 2, 3, 4, 5, 6, 7, 8, 10, or 15.

[0041] In the present application, "cycloalkyl" means an alkyl group in which a plurality of carbon atoms (at least 3 carbon atoms) form a ring, for example, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, etc. The "cycloalkyl" of the present application can contain 3-50 carbon atoms, in some embodiments the number of carbon atoms in the cycloalkyl group can be 3-30, in other embodiments the number of carbon atoms in the cycloalkyl group can be 3-20, in other embodiments the number of carbon atoms in the cycloalkyl group can be 3-15. Of course, the number of carbon atoms in the cycloalkyl group can also be other numbers, for example, the number of carbon atoms in the cycloalkyl group can be 3, 4, 5, 6, 7, 8, 10, 12, 13, or 15.

[0042] In the present application, "aryl" refers to an optionally functionalized or substituted group derived from an aromatic carbocyclic ring. The aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups connected by a carbon-carbon bond in conjugation, a monocyclic aryl group and a fused ring aryl group connected by a carbon-carbon bond in conjugation, two or more fused ring aryl groups connected by a carbon-carbon bond in conjugation. That is, unless otherwise specified, two or more aromatic groups connected by a carbon-carbon bond in conjugation can also be considered as an aryl group in the present application. The "aryl" group in the present application can contain 6-50 carbon atoms, in some embodiments, the number of carbon atoms in the aryl group can be 6-30, in other embodiments, the number of carbon atoms in the aryl group can be 6-20, in other embodiments, the number of carbon atoms in the aryl group can be 6-15. Of course, the number of carbon atoms in the aryl group can also be other quantities, for example, the number of carbon atoms in the aryl group can be 6, 7, 8, 9, 10, 12, 13, 14 or 15.

[0043] In the present application, "heteroaryl" refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4 or 5 heteroatoms in the ring, which can be at least one of O, N, Si, S. The "heteroaryl" group in the present application can contain 3-50 carbon atoms, in some embodiments, the number of carbon atoms in the heteroaryl group can be 3-30, in other embodiments, the number of carbon atoms in the heteroaryl group can be 3-20, in other embodiments, the number of carbon atoms in the heteroaryl group can be 3-15. Of course, the number of carbon atoms in the heteroaryl group can also be other quantities, for example, the number of carbon atoms in the heteroaryl group can be 3, 5, 6, 8, 10, 12, 13, 14 or 15.

[0044] In the present application, "forming a cyclic structure" refers to the connection of two groups to each other by a chemical bond and optionally aromatization. In the present application, Ar1, Ar2 form a cyclic structure together with the carbon atom to which they are connected (the carbon atom in L1), in some embodiments, the number of carbon atoms in the cyclic structure is 3-8, in other embodiments, the number of carbon atoms in the cyclic structure is 5-6; the cyclic structure includes but is not limited to cyclopropane group, cyclobutane group, cyclopentane group, cyclohexane group, cycloheptane group. In the present application, the cyclic structure formed by Ar1, Ar2 together with the carbon atom to which they are connected can be fused with a benzene ring, including but not limited to benzo-cyclopropane group, benzo-cyclobutane group, benzo-cyclopentane group (such as, ), benzo-cyclohexane group (such as, ), benzo-cycloheptane group.

[0045] In the present application, the halogen group can include fluorine, iodine, bromine, chlorine, etc.

[0046] The embodiment of the present application provides a kind of organic compound, and the structure of organic compound is as shown in formula 1:

[0047] Wherein, R is

[0048] L1 is selected from substituted or unsubstituted alkylene with carbon number being 1-5;

[0049] Ar1, Ar2 is same or different, each is independently selected from hydrogen, substituted or unsubstituted alkyl with carbon number being 1-50, substituted or unsubstituted heteroalkyl with carbon number being 1-50, substituted or unsubstituted cycloalkyl with carbon number being 3-50, substituted or unsubstituted aryl with carbon number being 6-50, substituted or unsubstituted heteroaryl with carbon number being 3-50;Or Ar1, Ar2 together with the carbon atom connected form cyclic structure;

[0050] In Ar1 and Ar2, the heteroatom in heteroalkyl is selected from N, O, S, Si;

[0051] In Ar1 and Ar2, the heteroatom in heteroaryl is selected from N, O, S, Si;

[0052] The substituent group in L1, Ar1 and Ar2 is same or different, each is independently selected from halogen group, nitro group, cyano group, mercapto group.

[0053] In some optional embodiments, Ar1, Ar2 is same or different, each is independently selected from hydrogen, substituted or unsubstituted alkyl with carbon number being 1-30, substituted or unsubstituted heteroalkyl with carbon number being 1-30, substituted or unsubstituted cycloalkyl with carbon number being 3-30, substituted or unsubstituted aryl with carbon number being 6-30, substituted or unsubstituted heteroaryl with carbon number being 3-30;Or Ar1, Ar2 together with the carbon atom connected form cyclic structure with carbon being 3-8.

[0054] In some optional embodiments, Ar1, Ar2 is same or different, each is independently selected from hydrogen, substituted or unsubstituted alkyl with carbon number being 1-10, substituted or unsubstituted heteroalkyl with carbon number being 1-10, substituted or unsubstituted cycloalkyl with carbon number being 3-10, substituted or unsubstituted aryl with carbon number being 6-15, substituted or unsubstituted heteroaryl with carbon number being 3-15;Or Ar1, Ar2 together with the carbon atom connected form cyclic structure with carbon being 5-6.

[0055] In some optional embodiments, L1 is selected from substituted or unsubstituted methylene, substituted or unsubstituted ethylene, substituted or unsubstituted propylene, substituted or unsubstituted butylene;

[0056] the substituents in L1are selected from the group consisting of F, Cl, Br, nitro, cyano, thiol.

[0057] In some alternative embodiments, L1is selected from the group consisting of methylene, ethylene, propylene, butylene.

[0058] In some alternative embodiments, Ar1, Ar2are the same or different, each independently selected from the group consisting of hydrogen,

[0059] wherein Y is selected from the group consisting of a single bond, substituted or unsubstituted

[0060] R1is selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group having 1-10 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1-10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-10 carbon atoms, a substituted or unsubstituted aryl group having 6-15 carbon atoms, a substituted or unsubstituted heteroaryl group having 3-15 carbon atoms;

[0061] In R1, the heteroatom in the heteroalkyl group is selected from the group consisting of N, O, S, Si;

[0062] In R1, the heteroatom in the heteroaryl group is selected from the group consisting of N, O, S, Si;

[0063] m1, m2are the same or different, 0≤m1≤20, 0≤m2≤20, and m1+m2≤30;

[0064] the substituents in Y and R1are the same or different, each independently selected from the group consisting of F, Cl, Br, nitro, cyano, amino, thiol.

[0065] In some alternative embodiments, m1, m2are the same or different, 0≤m1≤10, 0≤m2≤10, and m1+m2≤15.

[0066] In some alternative embodiments, R1is selected from the group consisting of hydrogen, a substituted or unsubstituted W group;

[0067] the unsubstituted W group is selected from the group consisting of:

[0068] methyl, ethyl, propyl, butyl,

[0069] the substituted W group has one or more than two substituents, each of the substituents is independently selected from the group consisting of F, Cl, Br, nitro, cyano, amino, thiol, CF3; when the number of substituents is more than two, any two of the substituents are the same or different.

[0070] In some alternative embodiments, Ar1, Ar2are the same or different, each independently selected from the group consisting of hydrogen,

[0071] In some alternative embodiments, when one of Ar1and Ar2is selected from substituted or unsubstituted alkyl having a carbon number of 1-15, substituted or unsubstituted heteroalkyl having a carbon number of 3-15, and the other is selected from substituted or unsubstituted aryl having a carbon number of 6-20, substituted or unsubstituted heteroaryl having a carbon number of 3-20, Ar1, Ar2together with the carbon atom to which they are attached form a cyclic structure. For example, Ar1, Ar2together with the carbon atom (the carbon atom in L1) to which they are attached form a five-membered cyclic structure or a six-membered cyclic structure

[0072] In some alternative embodiments, R is selected from

[0073] In some alternative embodiments, the organic compound is selected from one of the following compounds:

[0074] Embodiments of the present application provide a preparation method of the organic compound provided in any of the above embodiments, comprising:

[0075] Step S110: performing an amino acylation reaction on decalin as a raw material A with 1-piperidine carbonyl chloride to obtain an intermediate product B,

[0076] Step S120: performing a hydrolysis reaction on the intermediate product B with hydrobromic acid to obtain an intermediate product C,

[0077] Step S130: performing a condensation reaction on the intermediate product C with a primary amine to obtain a final product D,

[0078] In some alternative embodiments, the preparation method of the organic compound comprises:

[0079] Step S110: performing an amino acylation reaction on raw material A (decalin) and 1-piperidine carbonyl chloride in a mixed solution of AlCl3and o-dichlorobenzene, the reaction temperature is 0-175°C, the reaction time is 3-5 days at 175°C to obtain decalin-3,4,9,10,15,16-hexyl hexa(piperidin-1-ylmethanone) (i.e., the intermediate product B),

[0080] Step S120: refluxing the intermediate B in a hydrobromic acid solution for 0.5-2 hours to perform a hydrolysis reaction, to obtain decene-3,4,9,10,15,16-hexacarboxylic acid trihydride (i.e., intermediate C),

[0081] Step S130: performing a condensation reaction of the intermediate C and a primary amine (R-NH2) in a suspension of N,N-dimethylformamide (DMF) at a reaction temperature of 90-140°C for 12-28 hours to obtain N-R-decacyclene-3,4,9,10,15,16-hexacarboxylic acid triimide (i.e., final product D),

[0082] The preparation method of the organic compound of the present application will be described in detail below in conjunction with examples, however, the following description is used to explain the present application, and is not intended to limit the scope of the present application in any way.

[0083]

Compound 1

[0084] The preparation method of Compound 1 is as follows:

[0085] Step S110: performing an aminoacylation reaction of the starting material A (decacyclene) and 1-piperidine carbonyl chloride in a mixed solution of AlCl3and o-dichlorobenzene at a reaction temperature of 0-175°C, and the reaction time is 4 days at 175°C to obtain decacyclene-3,4,9,10,15,16-hexyl hexa(piperidin-1-ylmethanone) (i.e., intermediate B),

[0086] At 0°C, AlCl3(2.8 g, 21.0 mmol) was added to a mixture of starting material A (decacyclene) (0.75 g, 1.66 mmol), 1-piperidine carbonyl chloride (3.12 mL, 25.0 mmol), and o-dichlorobenzene (o-DCB, 7.5 mL). The mixture was stirred at 80°C for 2 hours, and then cooled to room temperature. Additional AlCl3(1.64 g, 12.3 mmol) and 1-piperidine carbonyl chloride (0.9 mL, 7.2 mmol) were added, and the mixture was stirred at 135°C overnight, and then warmed to 175°C and stirred for four days. The mixture was cooled to room temperature, and then poured into 50 mL of 5% HCl. The mixture was extracted with chloroform (100 mL) three times, and the organic phase was dried with NaSO4, filtered, and concentrated under vacuum. Acetone (250 mL) was added, and the suspension was filtered to obtain a yellow-brown solid. The solid was suspended in 200 mL of hot chloroform solution, and filtered through diatomite. The filtrate was separated by column chromatography, and eluted with chloroform (pure) to acetone: chloroform = 3:20 to obtain intermediate B (0.89 g, 0.80 mmol, 48%) in yellow solid.

[0087] The structural characterization parameters of the intermediate product B are: 1 H NMR (500 MHz, CDC13): δ 8.76 (m, 6H), 7.72 (m, 6H), 4.24 (br, 6H), 3.42-3.36 (m, 18H), 1.81-1.50 (m, 48H); 13 C NMR (125 MHz, CDC13): δ 168.91, 168.86, 137.84, 136.07, 135.12, 127.30, 124.97, 123.45, 48.91, 42.66, 26.07, 25.56, 24.84; FDMS (m / z): [M + ] calcd. for C 72 H 72 N6O6, 1116.6; found, 1116.5.

[0088] Step S120: refluxing the intermediate product B in a hydrobromic acid solution for 1 hour to obtain decene-3,4,9,10,15,16-hexacarboxylic acid trihydrogen (i.e., the intermediate product C),

[0089] A suspension of the intermediate product B (0.57 g, 0.51 mmol) in hydrobromic acid (HBr) (aq, 38 mL, 48%) was refluxed for 1 hour; the mixture was cooled to room temperature and filtered; the precipitate was washed with water, acetone and dichloromethane and then dried under vacuum at 80 °C overnight to obtain the intermediate product C (0.33 g, 0.50 mmol, 97%) as a red solid.

[0090] It is to be noted that the intermediate product C obtained in step S120 can be directly used in the next reaction without further purification.

[0091] Step S130: condensing the intermediate product C and the primary amine (9-aminheptadecane) in a suspension of N,N-dimethylformamide (DMF) at a reaction temperature of 120 °C for 24 hours to obtain the final product D-1 (compound 1),

[0092] A suspension of intermediate C (0.56 g, 0.85 mmol), 9-aminohexadecane (1.30 g, 5.1 mmol), and DMF (24 mL) was heated at 120 °C for 24 h. The mixture was cooled to room temperature and then poured into 90 mL of 2 M HC1. The mixture was extracted with CHCI3 three times, the organic phase was dried over MgS04, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (60% DCM / hexanes) to give compound 1 (710 mg, 61%) as an orange or red solid.

[0093] The structural characterization parameters of compound 1 are: 1 H NMR (500 MHz, CDC13): δ 8.70 (br, 6H), 8.65 (br, 6H), 5.23 (p, J = 7.0 Hz, 3H), 2.28 (m, 6H), 1.92 (m, 6H), 1.42-1.26 (m, 72H), 0.95-0.81 (m, 18H); 13 C NMR (125 MHz, CDC13): δ 163.67, 162.65, 139.00, 137.23, 132.39, 131.34, 130.63, 125.03, 123.91, 123.69, 122.81, 55.08, 32.77, 31.97, 29.79, 29.75, 29.71, 29.45, 29.41, 27.51, 22.73, 14.13; FD-MS (m / z): [M + ] calcd. for C 93 H 117 N3O6, 1371.9; found, 1372.1.

[0094]

Compound 2

[0095] Compound 2 was prepared according to the procedure for the preparation of compound 1, except that step S130 for the synthesis of compound 2 was: condensation of intermediate C and a primary amine (2-ethyl-1-hexylamine) in a suspension of DMF at a reaction temperature of 120 °C for 24 h to give final product D-2 (compound 2),

[0096] A suspension of intermediate C (0.4 g, 0.61 mmol), 2-ethyl-1-hexylamine (780 mg, 6.0 mmol) and DMF (25 mL) was heated at 120 °C for 24 h. The mixture was cooled to room temperature and then poured into 60 mL of 2 M HC1. The mixture was extracted with CHCI3 three times, the organic phase was dried over MgS04, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (3% acetone / CHCI3) to give compound 2 (310 mg, 52%) as an orange / red solid.

[0097] The structural characterization parameters of compound 2 are: 1 H NMR (500 MHz, CDCI3): δ 7.41 (br, 6H), 6.78 (br, 6H), 3.87 (m, 3H), 3.78 (m, 3H), 1.82 (br, 3H), 1.37-1.21 (m, 24H), 0.96-0.89 (m, 18H); 13 C NMR (125 MHz, CDCI3): δ 162.25, 137.85, 136.07, 131.39, 130.30, 124.10, 123.34, 122.51, 44.52, 38.22, 30.87, 28.81, 24.07, 23.44, 14.40, 10.69; FD-MS (m / z): [M + ] calcd. for C 66 H 63 N3O6, 993.5; found, 993.4.

[0098]

Compound 3

[0099] Compound 3 was prepared according to the preparation method of compound 1, except that step S130 for synthesizing compound 3 was condensation reaction of intermediate C and primary amine (1-octylamine) in DMF, the reaction temperature was 120 °C, and the reaction time was 24 h, to obtain final product D-3 (compound 3),

[0100] A suspension of intermediate C (0.10 g, 0.15 mmol), 1-octylamine (200 mg, 1.5 mmol) and DMF (6 mL) was heated at 120 °C for 24 h. The mixture was cooled to room temperature and then poured into 30 mL of 2 M HC1. The mixture was extracted with CHCI3 three times, the organic phase was dried over MgS04, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (2% acetone / CHCI3) to give compound 3 (57 mg, 38%) as an orange / red solid.

[0101] The structural characterization parameters of compound 3 are as follows: 1 H NMR (500 MHz, CDC13): δ 8.56 (br, 6H), 8.50 (br, 6H), 4.26 (t, J = 7.2 Hz, 6H), 1.84 (m, 6H), 1.46 (m, 6H), 1.35 (m, 24H), 0.94 (t, J = 6.7 Hz, 9H); 13 C NMR (125 MHz, CDC13): δ 162.25, 137.85, 136.07, 131.39, 130.30, 124.10, 123.34, 122.51, 44.52, 38.22, 30.87, 28.81, 24.07, 23.44, 14.40, 10.69; FD-MS (m / z): [M + ] calcd. For C 66 H 63 N3O6, 993.5; found, 993.4.

[0102]

Compound 4

[0103] Compound 4 was prepared according to the preparation method of reference compound 1, except that step S130 for synthesizing compound 4 was as follows: intermediate product C and primary amine (4-fluoro-methylbenzylamine) were subjected to condensation reaction in a suspension of DMF, the reaction temperature was 110°C, and the reaction time was 16 hours, to obtain final product D-4 (compound 4),

[0104] A suspension of intermediate product C (0.10 g, 0.15 mmol), 4-fluoro-methylbenzylamine (209 mg, 1.5 mmol) and DMF (20 mL) was heated at 110°C for 16 hours. The mixture was cooled to room temperature and then poured into 30 mL of 2M HCl. The mixture was extracted with CHCl3 three times, the organic phase was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (5% acetone in DCM) to give compound 4 (70 mg, 45%) as a black-red solid.

[0105] The structural characterization parameters of compound 4 are as follows: 1 H NMR (500 MHz, CDC13): δ 8.55 (br, 6H), 8.10 (br, 6H), 7.29-7.16 (m, 6H), 7.07-6.91 (m, 6H), 5.83 (qt, J = 7.5, 1.0 Hz, 3H), 1.64 (s, 9H); 13C NMR (125 MHz, CDC13): δ 163.83, 163.46, 161.44, 138.91, 138.88, 135.90, 133.10, 132.99, 128.89, 128.68, 128.62, 127.99, 125.46, 122.77, 115.65, 115.49, 53.49, 18.99; FD-MS (m / z): [M+] calcd for C 66 H 36 F3N3O6, 1024.0; found, 1024.1.

[0106] Compound 5

[0107] Compound 5 was prepared according to the procedure for the preparation of Reference Compound 1, except that in Step S130, the condensation reaction of intermediate C and primary amine (methyl 2-amino-2-phenylacetate) was carried out in a suspension of DMF at 90 °C for 12 h to give the final product D-5 (Compound 5),

[0108] A suspension of intermediate C (0.10 g, 0.15 mmol), methyl 2-amino-2-phenylacetate (248 mg, 1.5 mmol) and DMF (15 mL) was heated at 90 °C for 12 h. The mixture was cooled to room temperature and then poured into 30 mL of 2 M HC1. The mixture was extracted with CHCI3 three times, the organic extracts were dried over MgS04, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (2% acetone / CHCI3) to give Compound 5 (84 mg, 51%) as an orange-red solid.

[0109] The structural characterization parameters of Compound 5 are: 1 H NMR (500 MHz, CDC13): δ 8.55 (br, 6H), 8.10 (br, 6H), 7.46-7.23 (m, 15H), 6.01 (t, J = 0.9 Hz, 3H), 3.72 (s, 9H); 13 C NMR (125 MHz, CDC13): δ 170.76, 162.86, 136.08, 135.90, 133.10, 132.96, 129.24, 128.99, 128.83, 127.98, 127.74, 125.21, 122.78, 58.01, 52.11. FD-MS (m / z): [M+] calcd for C 69 H 39 N3O 12, 1101.25; found, 1101.24.

[0110] Compound 6

[0111] Compound 6 was prepared according to the procedure for the preparation of Reference Compound 1, except that Step S130 for the synthesis of Compound 6 was condensation of intermediate C and primary amine (2,3-dihydro-lH-inden-l-amine) in a suspension of DMF at 110 °C for 16 h to give final product D-6 (Compound 6),

[0112] A suspension of intermediate C (0.10 g, 0.15 mmol), 2,3-dihydro-lH-inden-l-amine (200 mg, 1.5 mmol) and DMF (30 mL) was heated at 110 °C for 16 h. The mixture was cooled to room temperature and then poured into 30 mL of 2 M HC1. The mixture was extracted with CHCI3 three times, the organic extracts were dried over MgS04, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (1% acetone / CHCI3) to give Compound 6 (71 mg, 47%) as a bright yellow solid.

[0113] The structural characterization parameters of Compound 6 are: 1 H NMR (500 MHz, CDCI3): δ 8.55 (br, 6H), 8.10 (br, 6H), 7.24 (d br, 6H), 7.21-7.12 (m, 6H), 5.55-5.27 (m, 3H), 3.06-2.94 (m, 6H), 2.26 (ddt, J = 12.3, 6.8, 5.4 Hz, 3H), 2.11 (ddt, J = 12.5, 7.0, 5.5 Hz, 3H); 13 CNMR (125 MHz, CDCI3): δ 163.94, 143.00, 142.76, 135.90, 133.10, 132.99, 128.91, 127.99, 127.29, 126.32, 125.52, 125.47, 125.41, 122.77, 60.61, 34.44, 30.29. FD-MS (m / z): [M+] calcd. for C 69 H 39 N3O 12 , 1105.28; found, 1101.29.

[0114] Compound 7

[0115] Compound 7 was prepared according to the procedure for the preparation of Compound 1, except that step S130 for the synthesis of Compound 7 was condensation of intermediate C and primary amine (1,2,3,4-tetrahydro-1-naphthylamine) in a suspension of DMF at 120 °C for 24 h to give final product D-7 (Compound 7),

[0116] A suspension of intermediate C (0.10 g, 0.15 mmol), 1,2,3,4-tetrahydro-1- naphthylamine (220 mg, 1.5 mmol) and DMF (30 mL) was heated at 120 °C for 24 h. The mixture was cooled to room temperature and then poured into 30 mL of 2 M HC1. The mixture was extracted with CHCI3 three times, the organic extracts were dried over MgS04, filtered, and concentrated in vacuo. The resulting product was washed with methanol to give Compound 7 (83 mg, 53%) as a bright yellow solid.

[0117] The structural characterization parameters of Compound 7 are: 1 H NMR (500 MHz, CDC13): δ 8.56 (dd, J = 8.6, 7.7 Hz, 2H), 8.17 (d, J = 8.6 Hz, 1H), 8.10 (dd, J = 8.5, 2.3 Hz, 1H), 7.28-7.21 (m, 1H), 7.22-7.15 (m, 2H), 7.15-7.10 (m, 1H), 5.45-5.41 (m, 1H), 2.78 (td, J = 7.0, 1.0 Hz, 2H), 2.16 (ddt, J = 12.4, 8.1, 6.4 Hz, 1H), 2.03 (ddt, J = 12.4, 7.1, 6.4 Hz, 1H), 1.89 (dqd, J = 7.9, 6.4, 2.0 Hz, 2H). Due to the low solubility of this product in deuterated chloroform, only the hydrogen spectrum was obtained, and the carbon spectrum was not obtained. FD-MS (m / z): [M+] calcd for C 72 H 45 N3O6, 1048.33; found, 1048.33.

[0118]

Compound 8

[0119] Compound 8 was prepared according to the procedure for the preparation of Compound 1, except that step S130 for the synthesis of Compound 8 was condensation of intermediate C and primary amine (benzylamine) in a suspension of DMF at 100 °C for 12 h to give final product D-8 (Compound 8),

[0120] A suspension of intermediate C (0.10 g, 0.15 mmol), benzylamine (160 mg, 1.5 mmol) and DMF (30 mL) was heated at 100 °C for 12 h. The mixture was cooled to room temperature and then poured into 30 mL of 2 M HC1. The mixture was extracted with CHCI3 three times, the organic extract was dried over MgS04, filtered, and concentrated in vacuo. The resulting product was washed with methanol to give compound 8 as a red solid (77 mg, 55%).

[0121] The structural characterization parameters of compound 8 are: 1 H NMR (500 MHz, CDC13): δ 8.53 (br, 6H), 8.10 (br, 6H), 7.41-7.18 (m, 15H), 5.28 (t, J = 1.0 Hz, 6H). Due to the low solubility of this product in deuterated chloroform, only the hydrogen spectrum can be measured, and the carbon spectrum is not obtained. FD-MS (m / z): [M+] calcd. for: C 63 H 33 N3O6, 927.23; found, 927.24.

[0122]

Compound 9

[0123] Compound 9 was prepared according to the preparation method of reference compound 1, except that step S130 for synthesizing compound 9 was: condensation reaction of intermediate C and primary amine (aspartic acid dimethyl ester) in a suspension of DMF, the reaction temperature was 90 °C, and the reaction time was 12 h, to obtain final product D-9 (compound 9),

[0124] A suspension of intermediate C (0.10 g, 0.15 mmol), aspartic acid dimethyl ester (241 mg, 1.5 mmol) and DMF (30 mL) was heated at 90 °C for 12 h. The mixture was cooled to room temperature and then poured into 30 mL of 2 M HC1. The mixture was extracted with CHCI3 three times, the organic extract was dried over MgS04, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0.5% acetone / CHCI3) to give compound 9 as a dark red solid (57 mg, 35%).

[0125] The structural characterization parameters of compound 9 are: 1 H NMR (500 MHz, CDC13): δ 8.50 (br, 6H), 8.10 (br, 6H), 5.14 (t, J = 8.8 Hz, 3H), 3.67 (d, J = 12.6 Hz, 18H), 3.11-2.88 (m, 6H); 13C NMR (125 MHz, CDC13): δ 170.53, 170.01, 163.27, 135.90, 133.10, 132.96, 128.98, 127.98, 125.17, 122.78, 52.10, 51.80, 49.75, 36.11. FD-MS (m / z): [M+] calcd for C 60 H 39 N3O 18 , 1089.22; found, 1089.23.

[0126] Compound 10

[0127] Compound 10 was prepared according to the procedure for the preparation of Reference Compound 1, except that in Step S130, the condensation reaction of intermediate C and primary amine (L-phenylalanine benzyl ester) was carried out in a suspension of DMF at 100 °C for 15 h to give the final product D-10 (Compound 10),

[0128] A suspension of intermediate C (0.10 g, 0.15 mmol), L-phenylalanine benzyl ester (383 mg, 1.5 mmol) and DMF (30 mL) was heated at 100 °C for 15 h. The mixture was cooled to room temperature and then poured into 30 mL of 2 M HC1. The mixture was extracted with CHCI3 three times, the organic extracts were dried over MgS04, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (1% acetone / CHCI3) to give Compound 10 (91 mg, 44%) as a bright yellow solid.

[0129] The structural characterization parameters of Compound 10 are: 1 H NMR (500 MHz, CDC13): δ 8.50 (br, 6H), 8.10 (br,, 6H), 7.37-7.33 (m, 12H), 7.32-7.20 (m, 12H), 7.16 (m, 6H), 5.16 (t, J = 1.0 Hz, 6H), 5.08 (t, J = 8.6 Hz, 3H), 3.36 (ddt, J = 13.3, 8.6, 0.9 Hz, 3H), 3.28 (ddt, J = 13.2, 8.6, 0.9 Hz, 3H); 13C NMR (125 MHz, CDC13): δ 171.08, 163.80, 135.50, 135.27, 134.71, 132.08, 130.57, 130.43, 130.19, 129.25, 128.92, 128.68, 128.58, 127.54, 127.46, 125.17, 121.01, 66.93, 55.45, 37.46. FD-MS (m / z): [M+] calcd for C 90 H 57 N3O 12 , 1371.39; found, 1371.40.

[0130] Compound 11 was prepared according to the procedure for the preparation of Reference Compound 1, except that in Step S130, the condensation reaction of intermediate C and primary amine (L-glutamic acid dibenzyl ester) was carried out in a suspension of DMF at 100 °C for 15 h to give the final product D-11 (Compound 11),

[0131] Compound 11 was prepared according to the procedure for the preparation of Reference Compound 1, except that in Step S130, the condensation reaction of intermediate C and primary amine (L-glutamic acid dibenzyl ester) was carried out in a suspension of DMF at 100 °C for 15 h to give the final product D-11 (Compound 11),

[0132] A suspension of intermediate C (0.10 g, 0.15 mmol), L-glutamic acid dibenzyl ester (491 mg, 1.5 mmol) and DMF (30 mL) was heated at 100 °C for 15 h. The mixture was cooled to room temperature and then poured into 30 mL of 2 M HC1. The mixture was extracted with CHCl3 three times, the organic extracts were dried over MgS04, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (1% acetone / CHCl3) to give Compound 11 (95 mg, 40%) as a bright yellow solid.

[0133] The structural characterization parameters of Compound 11 are: 1 H NMR (500 MHz, CDC13): δ 8.50 (br, 6H), 8.10 (br, 6H), 7.38-7.32 (m, 24H), 7.32-7.26 (m, 6H), 5.30-4.99 (m, 15H), 2.63-2.37 (m, 6H), 2.37-2.21 (m, 6H); 13C NMR (125 MHz, CHCl3): δ 172.58, 171.32, 164.35, 136.33, 135.49, 135.27, 132.08, 130.57, 130.49, 130.43, 130.17, 128.68, 128.58, 128.55, 127.54, 125.17, 121.01, 66.93, 65.47, 53.64, 31.30, 26.33. FD-MS (m / z): [M+] calcd for C 99 H 69 N3O 18 ,1587.45; found, 1587.46.

[0134] Compound 12 was prepared according to the procedure for the preparation of Reference Compound 1, except that in Step S130, the condensation reaction of intermediate C and the primary amine (tert-butyl-L-tyrosine tert-butyl ester) was carried out in a suspension of DMF at a reaction temperature of 100 °C for a reaction time of 12 hours to yield the final product D-12 (Compound 12),

[0135] Compound 12 was prepared according to the procedure for the preparation of Reference Compound 1, except that in Step S130, the condensation reaction of intermediate C and the primary amine (tert-butyl-L-tyrosine tert-butyl ester) was carried out in a suspension of DMF at a reaction temperature of 100 °C for a reaction time of 12 hours to yield the final product D-12 (Compound 12),

[0136] A suspension of intermediate C (0.10 g, 0.15 mmol), tert-butyl-L-tyrosine tert-butyl ester (495 mg, 1.5 mmol), and DMF (30 mL) was heated at 100 °C for 12 hours. The mixture was cooled to room temperature and then poured into 30 mL of 2 M HC1. The mixture was extracted with CHCl3 three times, the organic extracts were dried over MgS04, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0.8% acetone / CHCl3) to yield Compound 12 (91 mg, 41%) as a bright yellow solid.

[0137] The structural characterization parameters of Compound 12 are: 1 H NMR (500 MHz, CDCl3): δ 8.50 (br, 6H), 8.10 (br, 6H), 7.07 (d br 6H), 6.85-6.77 (m, 6H), 5.03 (q, J = 8.2 Hz, 3H), 3.37 (m, 3H), 3.29 (m 3H), 1.30 (s, 27H); 13C NMR (125 MHz, CDC13): δ 169.93, 163.80, 154.56, 135.27, 132.08, 130.51, 130.43, 130.19, 128.25, 127.54, 125.16, 121.01, 119.54, 82.26, 76.03, 55.15, 55.07, 37.09, 28.50, 27.57. FD-MS (m / z): [M+] calcd for C 93 H 87 N9O 15 , 1485.61; found, 1485.60.

[0138] Compound 13 was prepared according to the procedure for the preparation of Reference Compound 1, except that in Step S130, the condensation reaction of intermediate C and primary amine (methyl 4-amino-4-(l-naphthyl)butanoate) was carried out in a suspension of DMF at 120 °C for 12 h to give the final product D-13 (Compound 13),

[0139] Compound 13 was prepared according to the procedure for the preparation of Reference Compound 1, except that in Step S130, the condensation reaction of intermediate C and primary amine (methyl 4-amino-4-(l-naphthyl)butanoate) was carried out in a suspension of DMF at 120 °C for 12 h to give the final product D-13 (Compound 13),

[0140] A suspension of intermediate C (0.10 g, 0.15 mmol), methyl 4-amino-4-(l- naphthyl)butanoate (365 mg, 1.5 mmol) and DMF (30 mL) was heated at 120 °C for 12 h. The mixture was cooled to room temperature and then poured into 30 mL of 2 M HC1. The mixture was extracted with CHCI3 three times, the organic extracts were dried over MgS04, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0.8% acetone / CHCI3) to give Compound 13 as a solid (70 mg, 35%).

[0141] The structural characterization parameters of Compound 13 are: 1 H NMR (500 MHz, CDC13): δ 8.56 (dd, J = 8.6, 7.8 Hz, 6H), 8.17 (d, J = 8.5 Hz, 2H), 8.14-8.10 (m, 5H), 8.09 (d, J = 2.5 Hz, 2H), 7.87 (dt, J = 8.0, 1.6 Hz, 3H), 7.83 (dt, J = 7.4, 1.4 Hz, 3H), 7.57-7.49 (m, 6H), 7.48-7.43 (m, 3H), 7.39 (dd, J = 8.2, 1.2 Hz, 3H), 5.82 (t, J = 7.4 Hz, 3H), 3.64 (s, 9H), 2.66-2.44 (m, 6H), 2.27 (td, J = 8.3, 7.4 Hz, 6H).13 C NMR (125 MHz, CDC13): δ 173.52, 164.73, 139.71, 135.28, 135.16, 135.02, 134.29, 133.04, 132.48, 132.29, 131.30, 130.18, 129.92, 129.89, 129.81, 129.08, 127.67, 127.57, 127.55, 126.91, 126.83, 125.85, 125.59, 125.21, 124.67, 120.98, 120.85, 120.55, 54.82, 51.99, 30.73, 28.95. FD-MS (m / z): [M+] calcd for C 87 H 57 N3O 12 , 1335.39; found, 1335.43.

[0142] Compound 14

[0143] Compound 14 was prepared according to the procedure for the preparation of Reference Compound 1, except that Step S130 for the synthesis of Compound 14 was: condensation of intermediate C and primary amine (methyl 3-amino-lH-2-indolecarboxylate) in a suspension of DMF at a reaction temperature of 90 °C for a reaction time of 12 hours to give final product D-14 (Compound 14),

[0144] A suspension of intermediate C (0.10 g, 0.15 mmol), methyl 3-amino-lH-2-indolecarboxylate (285 mg, 1.5 mmol), and DMF (30 mL) was heated at 90 °C for 12 hours. The mixture was cooled to room temperature and then poured into 30 mL of 2 M HC1. The mixture was extracted with CHCI3 three times, the organic extracts were dried over MgS04, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0.8% acetone / CHCI3) to give Compound 14 as a solid (74 mg, 42%).

[0145] The structural characterization parameters of Compound 14 are: 1 H NMR (500 MHz, CDC13): δ 11.07 (s, 3H), 8.55 (t, J = 8.6 Hz, 6H), 8.16 (d, J = 8.5 Hz, 2H), 8.09 (dd, J = 11.9, 8.7 Hz, 4H), 7.97 (dt, J = 7.7, 0.9 Hz, 3H), 7.38 (dd, J = 4.9, 1.4 Hz, 6H), 7.26 (ddd, J = 7.7, 5.4, 4.1 Hz, 3H), 3.89 (s, 9H).13 C NMR (125 MHz, CDC13): δ 163.37, 160.54, 136.69, 136.49, 136.45, 136.27, 133.17, 133.11, 132.92, 132.88, 132.55, 128.91, 128.80, 128.44, 128.40, 126.89, 124.50, 123.19, 122.58, 122.32, 122.24, 122.13, 121.61, 121.16, 117.58, 114.11, 51.30. FD-MS (m / z): [M+] calcd for C 72 H 36 N6O 12 , 1176.23; found, 1176.22.

[0146] Compound 15 was prepared according to the procedure for the preparation of Reference Compound 1, except that in Step S130, the condensation reaction of intermediate C and primary amine (methyl 3-amino benzo[B]thiophene-2-carboxylate) was carried out in a suspension of DMF at 90 °C for 12 h to give the final product D-15 (Compound 15),

[0147] Step S130 for the synthesis of Compound 15 was carried out as follows: a suspension of intermediate C and primary amine (methyl 3-amino benzo[B]thiophene-2-carboxylate) in DMF was heated at 90 °C for 12 h to give the final product D-15 (Compound 15),

[0148] A suspension of intermediate C (0.10 g, 0.15 mmol), methyl 3-amino benzo[B]thiophene-2-carboxylate (311 mg, 1.5 mmol) and DMF (30 mL) was heated at 90 °C for 12 h. The mixture was cooled to room temperature and then poured into 30 mL of 2 M HC1. The mixture was extracted with CHCl3 three times, the organic extracts were dried over MgS04, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0.8% acetone / CHCl3) to give Compound 15 as a solid (77 mg, 42%).

[0149] The structural characterization parameters of Compound 15 are as follows: 1 H NMR (500 MHz, CDC13): δ 8.55 (d, J = 8.6 Hz, 6H), 8.11-8.02 (m, 9H), 7.85 (dd, J = 6.4, 1.5 Hz, 3H), 7.51 (td, J = 6.7, 1.2 Hz, 3H), 7.40 (td, J = 7.4, 1.3 Hz, 3H), 3.90 (s, 9H). 13C NMR (125 MHz, CDC13): δ 165.26, 163.79, 140.25, 136.29, 133.19, 133.07, 132.98, 131.50, 128.91, 128.37, 127.23, 125.47, 124.82, 124.52, 124.45, 124.21, 122.32, 51.52. FD-MS (m / z): [M+] calcd for C 72 H 33 N3O 12 S3, 1277.12; found, 1277.13.

[0150] Compound 16

[0151] Compound 16 was prepared according to the procedure for the preparation of Reference Compound 1, except that in Step S130, the condensation reaction of intermediate C and primary amine (N,N-dimethyl-1,3-diaminopropane) was carried out in a suspension of DMF at 110 °C for 12 h to give the final product D-16 (Compound 16),

[0152] A suspension of intermediate C (0.10 g, 0.15 mmol), N,N-dimethyl-1,3-diaminopropane (153 mg, 1.5 mmol) and DMF (30 mL) was heated at 110 °C for 12 h. The mixture was cooled to room temperature and then poured into 30 mL of 2 M HC1. The mixture was extracted with CHC13 three times, the organic extracts were dried over MgS04, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0.8% acetone / CHC13) to give Compound 16 as a solid (71 mg, 52%).

[0153] The structural characterization parameters of Compound 16 are: 1 H NMR (500 MHz, CDC13): δ 8.59-8.49 (m, 6H), 8.17 (d, J = 8.6 Hz, 2H), 8.11 (dd, J = 8.5, 5.9 Hz, 4H), 4.03 (t, J = 5.9 Hz, 6H), 2.53 (t, J = 6.5 Hz, 6H), 2.31 (s, 18H), 1.90-1.72 (m, 6H). 13C NMR (125 MHz, CDC13): δ 165.40, 136.83, 136.71, 136.11, 133.02, 132.97, 132.77, 132.67, 132.33, 129.13, 128.99, 128.16, 128.09, 124.77, 122.81, 122.70, 122.65, 55.95, 45.17, 40.61, 25.72. FD-MS (m / z): [M+] calcd for C 57 H 48 N6O6, 912.36; found, 912.40.

[0154] Compound 17

[0155] Compound 17 was prepared according to the procedure for the preparation of Reference Compound 1, except that in Step S130, the condensation reaction of intermediate C and the primary amine (ALPHA-(trifluoromethyl)-3-pyridinemethanamine dihydrochloride) was carried out in a suspension of DMF at a reaction temperature of 90 °C for a reaction time of 12 hours to give the final product D-17 (Compound 17),

[0156] A suspension of intermediate C (0.10 g, 0.15 mmol), ALPHA-(trifluoromethyl)-3- pyridinemethanamine dihydrochloride (319 mg, 1.5 mmol), and DMF (30 mL) was heated at 90 °C for 12 hours. The mixture was cooled to room temperature and then poured into 30 mL of 2 M HC1. The mixture was extracted with CHCI3 three times, the organic extracts were dried over MgS04, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0.8% acetone / CHCI3) to give Compound 17 as a solid (54 mg, 32%).

[0157] The structural characterization parameters of Compound 17 are: 1 H NMR (500 MHz, CDC13): δ 8.74 (t, J = 1.7 Hz, 3H), 8.57 (dd, J = 15.6, 8.6 Hz, 6H), 8.50 (dt, J = 4.8, 1.6 Hz, 3H), 8.17 (d, J = 8.6 Hz, 2H), 8.10 (dd, J = 8.5, 2.3 Hz, 4H), 7.78 (dt, J = 7.3, 1.9 Hz, 3H), 7.26 (dd, J = 7.3, 4.7 Hz, 3H), 6.03 (q, J = 9.0 Hz, 3H). 13C NMR (125 MHz, CDC13): δ 163.37, 163.34, 163.30, 163.27, 149.77, 149.75, 149.73, 149.72, 147.93, 136.83, 136.71, 136.11, 135.06, 135.04, 135.03, 135.01, 133.08, 133.03, 132.84, 132.70, 132.47, 129.05, 128.99, 128.79, 127.98, 126.91, 125.24, 125.05, 125.01, 124.96, 124.91, 124.76, 122.78, 122.70, 122.66, 122.62, 54.44, 54.22, 54.01, 53.79. FD-MS (m / z): [M+] calcd for C 63 H 27 F9O6N6, 1134.18; found, 1134.15.

[0158] Compound 18

[0159] Compound 18 was prepared according to the procedure for the preparation of Reference Compound 1, except that in Step S130, the condensation reaction of intermediate C and primary amine (1-(4-methoxyphenyl)ethylamine) was carried out in a suspension of DMF at 90 °C for 12 h to give the final product D-18 (Compound 18),

[0160] A suspension of intermediate C (0.10 g, 0.15 mmol), 1-(4-methoxyphenyl)ethylamine (227 mg, 1.5 mmol), and DMF (30 mL) was heated at 90 °C for 12 h. The mixture was cooled to room temperature and then poured into 30 mL of 2 M HC1. The mixture was extracted with CHCl3 three times, the organic extracts were dried over MgS04, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0.8% acetone / CHCl3) to give Compound 18 as a solid (68 mg, 43%).

[0161] The structural characterization parameters of Compound 18 are: 1H NMR (500 MHz, CDC13): δ 8.56 (dd, J = 8.6, 7.7 Hz, 6H), 8.17 (d, J = 8.6 Hz, 2H), 8.10 (dd, J = 8.5, 2.3 Hz, 4H), 7.29-7.17 (m, 6H), 6.88-6.73 (m, 6H), 5.83 (qt, J = 7.3, 1.0 Hz, 3H), 3.78 (s, 9H), 1.64 (s, 9H). 13 C NMR (125 MHz, CDC13): δ 163.83, 159.30, 136.83, 136.71, 136.58, 136.11, 133.08, 133.03, 132.84, 132.74, 132.47, 128.89, 128.87, 128.03, 127.99, 125.46, 122.77, 122.69, 122.66, 113.79, 55.32, 53.56, 18.96. FD-MS (m / z): [M+] calcd. for C 69 H 45 N3O9, 1059.31; found, 1059.30.

[0162] Compound 19

[0163] Compound 19 was prepared according to the procedure for the preparation of Reference Compound 1, except that in Step S130, the condensation reaction of intermediate C and primary amine (1-[4-(trifluoromethyl)phenyl]ethylamine) was carried out in a suspension of DMF at 100 °C for 12 h to give the final product D-19 (Compound 19),

[0164] A suspension of intermediate C (0.10 g, 0.15 mmol), 1-[4- (trifluoromethyl)phenyl]ethylamine (284 mg, 1.5 mmol), and DMF (30 mL) was heated at 100 °C for 12 h. The mixture was cooled to room temperature and then poured into 30 mL of 2 M HC1. The mixture was extracted with CHCI3 three times, the organic extracts were dried over MgS04, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0.8% acetone / CHCI3) to give Compound 19 as a solid (70 mg, 40%).

[0165] The structural characterization parameters of Compound 19 are: 1H NMR (500MHz, CDCl3): δ8.56 (dd, J=8.6, 7.7Hz, 6H), 8.17 (d, J=8.6Hz, 2H), 8.10 (dd, J=8.5, 2.3Hz,4H),7.67-7.55(m,6H),7.31-7.21(m,6H),5.83(qt,J=7.3,1.0Hz,3H),1.64(s,9H). 13 C NMR (125MHz, CDCl3): δ163.84,141.91,136.83,136.71,136.11,133.08,133.03,132 .84,132.74,132.47,131.15,130.89,130.63,130.38,128.89,128.87,127.99,127.8 2,127.80,127.78,127.77,127.22,125.78,125.75,125.71,125.68,125.46,125.08 ,122.94,122.77,122.69,122.66,120.79,53.70,19.05.FD-MS(m / z):[M+]calcd.for C 69 H 36 F9N3O6,1173.24; found,1173.28.

[0166]

Compound 20

[0167] Compound 20 was prepared using the same method as Compound 1, with the only difference being step S130. Step S130 for synthesizing Compound 20 involved condensing intermediate product C and primary amine (N-ethylurea) in a suspension of DMF at a reaction temperature of 100°C for 12 hours, yielding the final product D-20 (Compound 20).

[0168] A suspension of intermediate C (0.10 g, 0.15 mmol), N-ethylurea (396 mg, 4.5 mmol), and DMF (30 mL) was heated at 100 °C for 12 hours. The mixture was cooled to room temperature and then poured into 30 mL of 2 M HCl. The mixture was extracted three times with CHCl3, and the organic extract was dried over MgSO4, filtered, and concentrated under vacuum. The residue was purified by silica gel chromatography (0.8% acetone / CHCl3) to give solid compound 20 (39 mg, 30%).

[0169] The structural characterization parameters of compound 20 are as follows: 1H NMR (500 MHz, CDCI3): δ 8.56 (dd, J = 8.5, 6.9 Hz, 6H), 8.19-8.09 (m, 6H), 7.82 (t, J = 4.6 Hz, 3H), 3.26 (qd, J = 6.5, 4.5 Hz, 6H), 1.05 (t, J = 6.4 Hz, 9H). 13 C NMR (125 MHz, CDCI3): δ 166.07, 154.44, 136.69, 136.49, 136.45, 133.17, 133.11, 132.92, 132.61, 132.30, 129.26, 129.23, 128.26, 128.23, 123.76, 122.67, 122.63, 122.61, 35.30, 15.36. FD-MS (m / z): [M+] calcd. for C 51 H 30 N6O9, 870.20; found, 870.25.

[0170] The electronic transmission material provided by the embodiments of the present application comprises the organic compound provided by any of the embodiments of the present application.

[0171] In some optional embodiments, the preparation method of the electronic transmission material comprises: dissolving the organic compound in an organic solvent (for example, chloroform), and obtaining the electronic transmission material after stirring and dissolving, wherein the mass-volume ratio of the organic compound to the organic solvent is (1-20) mg / mL. Specifically, the mass-volume ratio of the organic compound to the organic solvent is 1 mg / mL, 2 mg / mL, 3 mg / mL, 5 mg / mL, 7 mg / mL, 10 mg / mL, 12 mg / mL, 15 mg / mL or 20 mg / mL.

[0172] The electronic element provided by the embodiments of the present application comprises oppositely arranged anode and cathode, and a functional layer arranged between the anode and the cathode; the functional layer comprises the organic compound provided by any of the embodiments of the present application.

[0173] The organic compound provided by any of the embodiments of the present application can be used to form at least one layer in a plurality of functional layers, so as to improve the voltage characteristics, current characteristics and efficiency characteristics of the electronic element. In some optional embodiments, the functional layer comprises an electronic transmission layer, and the electronic transmission layer comprises the organic compound provided by any of the embodiments of the present application.

[0174] The electronic element can be a perovskite solar cell, a module or an organic light emitting diode. For example, as shown in FIG. 1, the perovskite solar cell includes an anode 100 and a cathode 200 arranged oppositely, and a functional layer 300 arranged between the anode 100 and the cathode 200; the functional layer 300 contains the organic compound provided in any of the embodiments of the present application.

[0175] In some optional embodiments, as shown in FIG. 1, the functional layer 300 includes a hole transport layer 310, a perovskite light absorption layer 320, and an electron transport layer 330; the hole transport layer 310 is arranged between the anode 100 and the perovskite light absorption layer 320, and the electron transport layer 330 is arranged between the perovskite light absorption layer 320 and the cathode 200. In some optional embodiments, as shown in FIG. 1, the functional layer 300 further includes a cathode buffer layer 340 arranged between the electron transport layer 330 and the cathode 200. The electron transport layer 330 contains the organic compound provided in any of the embodiments of the present application.

[0176] For example, as shown in FIG. 1, the perovskite solar cell includes the anode 100, the hole transport layer 310, the perovskite light absorption layer 320, the electron transport layer 330, the cathode buffer layer 340 and the cathode 200 arranged in sequence. The electron transport layer 330 contains the organic compound provided in any of the embodiments of the present application.

[0177] In some optional embodiments, the anode is a conductive substrate, and the anode material includes one or more of indium tin oxide (ITO), indium zinc oxide (IZO), zinc tin oxide, tungsten oxide, tungsten-doped indium oxide (IWO), fluorine-doped tin oxide (FTO), cerium-doped indium oxide (ICO), aluminum-doped zinc oxide (AZO), and boron-doped zinc oxide (BZO). The conductive substrate can be cleaned, laser-etched, and treated with ozone. The step of cleaning the conductive substrate can include placing the conductive substrate in an ultrasonic cleaning instrument, and ultrasonically cleaning the conductive substrate with deionized water, acetone, and isopropanol, respectively, for 10-30 min at each step. The step of treating the conductive substrate with ozone can include treating the conductive substrate with a UV-zone, wherein the treatment time is 2-10 min.

[0178] In some optional embodiments, the material of the hole transport layer includes nickel oxide (NiO Xone or more of chlorobenzene, ethanol, isopropanol.

[0179] In some alternative embodiments, the method for preparing the perovskite light-absorbing layer includes: applying a perovskite precursor solution on the hole transport layer by slot-die coating to form the perovskite light-absorbing layer. In some alternative embodiments, the perovskite precursor solution includes a perovskite material and an organic solvent, the perovskite material is dissolved in the organic solvent to form the perovskite precursor solution, and after the perovskite precursor solution is applied on the surface of the hole transport layer, the organic solvent is removed by a post-processing process (e.g., a thermal annealing process, the annealing temperature is 100°C, and the annealing time is 40 min) to form the perovskite light-absorbing layer including the perovskite material.

[0180] In some alternative embodiments, the electron transport layer includes the organic compound provided in any of the embodiments to improve the electron transport performance of the electron transport layer. The electron transport layer can or can not contain other materials. The method for preparing the electron transport layer includes: dissolving the organic compound provided in any of the embodiments in an organic solvent (e.g., chloroform), stirring to obtain the electron transport material, and applying the electron transport material on the perovskite light-absorbing layer by spin coating to obtain the electron transport layer. The spin coating speed can be 2500-3500 rpm, and specifically can be 3000 rpm. The spin coating time can be 20-40 s, and specifically can be 30 s.

[0181] In some optional embodiments, the material of the cathode buffer layer comprises one or both of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) and zirconium acetylacetonate. In some optional embodiments, the preparation method of the cathode buffer layer comprises: dissolving the material of the cathode buffer layer in an organic solvent (e.g., ethanol), stirring to obtain a cathode buffer material solution, and coating the cathode buffer material solution on the electron transport layer by spin coating to obtain the cathode buffer layer.

[0182] In some optional embodiments, the cathode is an electrode, and the cathode material comprises one of silver, copper, transparent conductive oxide (TCO), and a carbon electrode. The cathode can be prepared by a method such as thermal evaporation, vacuum evaporation, sputtering, atomic layer deposition, etc. The thickness of the cathode can be 80-120 nm.

[0183] The preparation method of the perovskite solar cell of the present application will be described in detail below with reference to the embodiments, but the following description is used to explain the present application and is not intended to limit the scope of the present application in any way.

[0184] Embodiment 1

[0185] As shown in FIG. 1, the specific structure of the perovskite solar cell of the present embodiment is as follows:

[0186] The anode 100, the hole transport layer 310, the perovskite light-absorbing layer 320, the electron transport layer 330, the cathode buffer layer 340, and the cathode 200 are sequentially stacked.

[0187] The specific preparation process of the perovskite solar cell of the present embodiment is as follows:

[0188] S210: 10 mg of compound 1 is dissolved in 1 mL of chloroform, and stirred at room temperature to obtain a uniform electron transport material;

[0189] S220: An anode 100 is provided;

[0190] S230: Me-4PACz is dissolved in chlorobenzene to obtain a hole transport material solution, and the hole transport material solution is added dropwise on the upper surface of the anode 100 to form a hole transport layer 310;

[0191] S240: Lead iodide and iodomethylamine solids are dissolved in N,N-dimethylformamide (DMF) and stirred until completely dissolved to obtain a perovskite precursor solution, and the perovskite precursor solution is coated on the upper surface of the hole transport layer 310 to form a perovskite light-absorbing layer 320;

[0192] S250: The electron transport material is coated on the upper surface of the perovskite light-absorbing layer 320 by spin coating to form an electron transport layer 330;

[0193] S250: The BCP is dissolved in an ethanol solution to obtain a cathode buffer material solution with a mass / volume ratio of 0.5 mg / mL. The cathode buffer material solution is coated on the upper surface of the electron transport layer 330 by a spin coating method to form a cathode buffer layer 340.

[0194] S270: A cathode 200 is formed on the upper surface of the cathode buffer layer 340 by a vacuum evaporation method, and the thickness of the cathode 200 is 100 nm.

[0195] [Example 2]

[0196] The perovskite solar cell of Example 2 is prepared according to the preparation method of Example 1, except that Compound 1 is replaced by an equal mass of Compound 2.

[0197] [Example 3]

[0198] The perovskite solar cell of Example 3 is prepared according to the preparation method of Example 1, except that Compound 1 is replaced by an equal mass of Compound 3.

[0199] [Example 4]

[0200] The perovskite solar cell of Example 4 is prepared according to the preparation method of Example 1, except that Compound 1 is replaced by an equal mass of Compound 4.

[0201] [Example 5]

[0202] The perovskite solar cell of Example 5 is prepared according to the preparation method of Example 1, except that Compound 1 is replaced by an equal mass of Compound 5.

[0203] [Example 6]

[0204] The perovskite solar cell of Example 6 is prepared according to the preparation method of Example 1, except that Compound 1 is replaced by an equal mass of Compound 6.

[0205] [Example 7]

[0206] The perovskite solar cell of Example 7 is prepared according to the preparation method of Example 1, except that Compound 1 is replaced by an equal mass of Compound 7.

[0207] [Example 8]

[0208] The perovskite solar cell of Example 8 is prepared according to the preparation method of Example 1, except that Compound 1 is replaced by an equal mass of Compound 8.

[0209] [Example 9]

[0210] A perovskite solar cell of Example 9 was prepared according to the preparation method of Example 1, except that Compound 1 was replaced with an equal mass of Compound 9.

[0211] [Example 10]

[0212] A perovskite solar cell of Example 10 was prepared according to the preparation method of Example 1, except that Compound 1 was replaced with an equal mass of Compound 10.

[0213] [Example 11]

[0214] A perovskite solar cell of Example 11 was prepared according to the preparation method of Example 1, except that Compound 1 was replaced with an equal mass of Compound 11.

[0215] [Example 12]

[0216] A perovskite solar cell of Example 12 was prepared according to the preparation method of Example 1, except that Compound 1 was replaced with an equal mass of Compound 12.

[0217] [Example 13]

[0218] A perovskite solar cell of Example 13 was prepared according to the preparation method of Example 1, except that Compound 1 was replaced with an equal mass of Compound 13.

[0219] [Example 14]

[0220] A perovskite solar cell of Example 14 was prepared according to the preparation method of Example 1, except that Compound 1 was replaced with an equal mass of Compound 14.

[0221] [Example 15]

[0222] A perovskite solar cell of Example 15 was prepared according to the preparation method of Example 1, except that Compound 1 was replaced with an equal mass of Compound 15.

[0223] [Example 16]

[0224] A perovskite solar cell of Example 16 was prepared according to the preparation method of Example 1, except that Compound 1 was replaced with an equal mass of Compound 16.

[0225] [Example 17]

[0226] A perovskite solar cell of Example 17 was prepared according to the preparation method of Example 1, except that Compound 1 was replaced with an equal mass of Compound 17.

[0227] [Example 18]

[0228] A perovskite solar cell of Example 18 was prepared according to the preparation method of Example 1, except that compound 1 was replaced by an equal mass of compound 18.

[0229]

Example 19

[0230] A perovskite solar cell of Example 19 was prepared according to the preparation method of Example 1, except that compound 1 was replaced by an equal mass of compound 19.

[0231]

Example 20

[0232] A perovskite solar cell of Example 20 was prepared according to the preparation method of Example 1, except that compound 1 was replaced by an equal mass of compound 20.

[0233]

Example 21

[0234] A perovskite solar cell of Example 21 was prepared according to the preparation method of Example 6, except that S210 of Example 21 was: 5 mg of compound 6 was dissolved in 1 mL of chloroform, and stirred at room temperature to obtain a uniform electron transport material.

[0235]

Example 22

[0236] A perovskite solar cell of Example 22 was prepared according to the preparation method of Example 6, except that S210 of Example 22 was: 12 mg of compound 6 was dissolved in 1 mL of chloroform, and stirred at room temperature to obtain a uniform electron transport material.

[0237]

Example 23

[0238] A perovskite solar cell of Example 23 was prepared according to the preparation method of Example 6, except that S210 of Example 23 was: 15 mg of compound 6 was dissolved in 1 mL of chloroform, and stirred at room temperature to obtain a uniform electron transport material.

[0239]

Example 24

[0240] A perovskite solar cell of Example 24 was prepared according to the preparation method of Example 6, except that S210 of Example 24 was: 20 mg of compound 6 was dissolved in 1 mL of chloroform, and stirred at room temperature to obtain a uniform electron transport material.

[0241]

Comparative Example 1

[0242] A perovskite solar cell of Comparative Example 1 was prepared according to the preparation method of Example 1, except that S210 of Comparative Example 1 was: 10 mg of compound 6 was dissolved in 1 mL of chloroform, and stirred at room temperature to obtain a uniform electron transport material. 60(Fullerenes) were dissolved in 1 mL chloroform, stirred at room temperature to obtain a uniform electron transport material.

[0243] The performance of the perovskite solar cells provided in Examples 1-24 and Comparative Example 1 of the present application was tested, and the open-circuit voltage, fill factor, short-circuit current density, and photoelectric conversion efficiency of the corresponding cell devices were obtained, as shown in Table 1.

[0244] Table 1 Performance test results of perovskite solar cells of Examples 1-24 and Comparative Example 1

[0245] As can be seen from the data in Table 1, the devices prepared from Examples 1-24 and Comparative Example 1 of the present application were tested for performance, and compared with Comparative Example 1, the open-circuit voltage and short-circuit current density of the perovskite solar cells of Examples 1-24 of the present application were slightly improved, and the fill factor and photoelectric conversion efficiency were significantly improved. This indicates that the organic compounds of Examples 1-24 of the present application can effectively improve the film-forming performance of the electron transport layer, improve the quality of the electron transport layer, improve the electron mobility, promote charge transfer, and improve the stability of the device. Further analysis of the data in Examples 1-20 in Table 1 shows that when the organic compounds are different but the mass-volume ratio of the organic compound to chloroform is the same, i.e., 10 mg / mL, the photoelectric conversion efficiency of Examples 5-7, Example 10, and Example 11 is higher, at 18.21-18.35%, while the photoelectric conversion efficiency of Comparative Example 1 is only 14.66%; and the open-circuit voltage, fill factor, and short-circuit current density of Examples 5-7, Example 10, and Example 11 are also greatly improved, among which the performance of Example 6 (organic compound is compound 6) is particularly outstanding. In addition, comparing the data of Example 6 and Examples 21-24 shows that when the organic compounds are the same, i.e., compound 6, but the mass-volume ratio of compound 6 to chloroform is different, the performance of the corresponding devices is also different, and when the mass-volume ratio of compound 6 to chloroform is 10-20 mg / mL, the photoelectric conversion efficiency of the corresponding device is higher, at 18.35-18.97%, among which the photoelectric conversion efficiency of Example 23 (mass-volume ratio of compound 6 to chloroform is 15 mg / mL) is best.

[0246] In summary, the organic compound provided in the examples of the present application has decacyclene triimide (DTI) as the parent nucleus, and has three terminal substituents connected to the three N terminals of the parent nucleus, respectively. The three-dimensional core structure of the decacyclene triimide parent nucleus can increase the steric hindrance, effectively inhibit excessive aggregation of molecules, and maintain high electron mobility while inhibiting aggregation. By modifying the parent nucleus with terminal substituents, the terminal substituents The ten-ring ene triimide parent nucleus has a larger conjugated plane, so that it has a more matched LUMO energy level, and the electron transport can be effectively improved by increasing the degree of π-extension; the end substituent can also regulate the interface energy level, increase the solubility of the organic compound in the organic solvent, effectively improve the film forming property of the electron transport layer, facilitate the formation of a uniform and dense electron transport layer on the perovskite light absorbing layer and other functional layers, effectively reduce the direct contact between the perovskite light absorbing layer and other functional layers and the cathode, promote the charge transfer, and improve the stability of the device.

[0247] The electronic device (not shown) provided by the embodiments of the present application comprises the electronic element provided by any of the embodiments of the present application. Since the electronic device has any of the electronic elements described in the above electronic element embodiments, it has the same beneficial effects, which will not be described herein again.

[0248] It should be noted that the terms "length", "width", "thickness", "upper", "lower", "front", "rear", "left", "right", "vertical", "horizontal", "top", "bottom", "inner", "outer", and the like are only for the convenience of describing the present application and simplifying the description, and do not indicate or imply that the devices or elements referred to must have a particular orientation, be constructed and operated in a particular orientation, and therefore cannot be understood as limiting the present application. The orientation terms "inner" and "outer" refer to the inner and outer of the contour of each component itself. For example, if the devices in the drawings are inverted, the devices described as "above" or "on" other devices or structures will be positioned "below" or "under" the other devices or structures. Thus, the exemplary term "above" can include both "above" and "below" orientations. The devices can also be positioned in other different ways (rotated by 90 degrees or in other orientations), and the spatial relative descriptions used herein are interpreted accordingly.

[0249] It should be noted that the terms "first", "second", and the like in the specification and claims of the present application and the above drawings are used to distinguish similar objects, and do not necessarily indicate a specific order or sequence. It should be understood that the terms thus used can be interchanged under appropriate circumstances, so that the embodiments of the present application described herein can be implemented in an order other than that illustrated or described herein. In addition, the terms "include" and "have" and any variations thereof are intended to cover non-exclusive inclusion, for example, a process, method, system, product or device including a series of steps or units does not have to be limited to only those steps or units clearly listed, but can include other steps or units not clearly listed or inherent to the process, method, product or device.

[0250] It is also need to be explained that, in the present application, "one embodiment", "another embodiment", "embodiment" and the like refer to the specific features, structures or characteristics described in connection with the embodiment, which are included in at least one embodiment described generally in the present application. The same expression appearing in several places in the specification does not necessarily refer to the same embodiment. Further, when a specific feature, structure or characteristic is described in connection with any embodiment, it is claimed that the implementation of such feature, structure or characteristic in connection with other embodiments also falls within the scope of the present application.

[0251] In the above embodiments, the description of each embodiment has its own focus, and the parts not described in detail in a certain embodiment can be referred to the relevant description of other embodiments.

[0252] It is also need to be explained that, the above is only the preferred embodiment of the present application, and does not limit the patent protection scope of the present application, and any equivalent structure or equivalent process transformation using the content of the present application specification and drawings, or direct or indirect application in other related technical fields, are also included in the patent protection scope of the present application.

Claims

1. An organic compound, characterized by, The structure of the organic compound is shown in Formula 1: wherein R is L1is selected from substituted or unsubstituted alkylene having a carbon number of 1 to 5; Ar1, Ar2are the same or different, each independently selected from hydrogen, substituted or unsubstituted alkyl having a carbon number of 1 to 50, substituted or unsubstituted heteroalkyl having a carbon number of 1 to 50, substituted or unsubstituted cycloalkyl having a carbon number of 3 to 50, substituted or unsubstituted aryl having a carbon number of 6 to 50, substituted or unsubstituted heteroaryl having a carbon number of 3 to 50; or Ar1, Ar2together with the carbon atom to which they are attached form a ring structure; In Ar1and Ar2, the heteroatom in the heteroalkyl is selected from N, O, S, Si; In Ar1and Ar2, the heteroatom in the heteroaryl is selected from N, O, S, Si; The substituents in L1, Ar1and Ar2are the same or different, each independently selected from halogen group, nitro group, cyano group, thiol group.

2. The organic compound according to claim 1, characterized by L1is selected from substituted or unsubstituted methylene, substituted or unsubstituted ethylene, substituted or unsubstituted propylene, substituted or unsubstituted butylene; The substituents in L1are selected from F, Cl, Br, nitro group, cyano group, thiol group.

3. The organic compound according to claim 1, wherein L1is selected from methylene, ethylene, propylene, butylene.

4. The organic compound according to claim 1, wherein Ar1, Ar2are the same or different, each independently selected from the group consisting of hydrogen, wherein Y is selected from a single bond, substituted or unsubstituted R1is selected from hydrogen, substituted or unsubstituted alkyl having a carbon number of 1 to 10, substituted or unsubstituted heteroalkyl having a carbon number of 1 to 10, substituted or unsubstituted cycloalkyl having a carbon number of 3 to 10, substituted or unsubstituted aryl having a carbon number of 6 to 15, substituted or unsubstituted heteroaryl having a carbon number of 3 to 15; In R1, the heteroatom in the heteroalkyl is selected from N, O, S, Si; In R1, the heteroatom in the heteroaryl is selected from N, O, S, Si; m1, m2are the same or different, 0≤m1≤20, 0≤m2≤20, and m1+m2≤30; The substituents in Y and R1are the same or different, each independently selected from F, Cl, Br, nitro group, cyano group, amino group, thiol group.

5. The organic compound according to claim 4, characterized by R1is selected from hydrogen, substituted or unsubstituted W group; The unsubstituted W group is selected from the group consisting of: methyl, ethyl, propyl, butyl, The substituted W group has one or more than two substituents, each independently selected from F, Cl, Br, nitro group, cyano group, amino group, thiol group, CF3; when the number of substituents is more than two, any two substituents are the same or different. Two substituents are the same or different.

6. The organic compound according to claim 1, wherein Ar1, Ar2are the same or different, each independently selected from the group consisting of hydrogen, 7. The organic compound according to claim 1, wherein When one of Ar1and Ar2is selected from substituted or unsubstituted alkyl having a carbon number of 1 to 15, substituted or unsubstituted heteroalkyl having a carbon number of 3 to 15, and the other is selected from substituted or unsubstituted aryl having a carbon number of 6 to 20, substituted or unsubstituted heteroaryl having a carbon number of 3 to 20, Ar1, Ar2together with the carbon atom to which they are attached form a ring structure.

8. The organic compound according to claim 1, wherein R is selected from 9. The organic compound according to claim 1, wherein The organic compound is selected from one of the following compounds:

10. A method for producing the organic compound according to claim 1, characterized by, Comprising: With decalin as raw material A, amino acylation reaction with 1-piperidine carbonyl chloride, to obtain intermediate product B, hydrolysis reaction with hydrobromic acid to obtain intermediate product C, condensation reaction with primary amine to obtain final product D, 11. An electron transport material, characterized in that, The organic compound of claim 1.

12. An electronic component, characterized by comprising: Comprising oppositely disposed anode and cathode, and a functional layer disposed between the anode and the cathode; the functional layer comprises the organic compound of claim 1.

13. The electronic component of claim 12, wherein, The electronic element is a perovskite solar cell or an organic light-emitting diode.

14. The electronic component of claim 12, wherein, The functional layer comprises an electron transport layer, and the electron transport layer comprises the organic compound.

15. An electronic device, comprising: The electronic element of claim 12. The electronic element of claim 12.

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