Organic compound as well as preparation method and application thereof

Abstract

The embodiment of the invention provides an organic compound as well as a preparation method and application thereof. Compared with the prior art, the organic compound provided by the embodiment of the invention takes decacycloalkene triimide (DTI) as a parent nucleus, has three terminal substituent groups which are respectively connected with three N terminals of the parent nucleus, and has relatively large steric hindrance and a conjugate plane, so that electrons have relatively high mobility, and electron transmission is effectively improved; the terminal substituent group can regulate and control the interface energy level, increase the solubility of the organic compound in an organic solvent, and effectively improve the film-forming property of the electron transport layer. Therefore, as an electron transport material, the organic compound provided by the embodiment of the invention can promote charge transfer and improve the stability of an electronic device.

Description

Technical Field

[0001] The present application relates to the technical field of organic electroluminescent materials, and in particular to an organic compound and a preparation method and application thereof, wherein the application mainly refers to the application of the organic compound in the field of electron transport materials, electronic components or electronic devices. Background Art

[0002] Perovskite solar cells (PSCs) have attracted widespread attention in recent years as an efficient and low-cost alternative to traditional solar energy conversion. The electron transport layer in inverse perovskite solar cells 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. The synthesis is difficult and the synthesis steps require 6 to 7 steps, so the synthesis cost is high. Fullerenes and their derivatives are also difficult to modify, with poor compound solubility, single energy level adjustability, poor stability in air, and poor film-forming properties, which leads to poor device performance.

[0003] Therefore, there is an urgent need to study 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 be able to improve the film-forming properties of the electron transport layer and promote charge transfer in order to enhance the stability of electronic devices. Summary of the invention

[0004] The embodiments of the present application provide an organic compound and a preparation method and application thereof to solve or alleviate the technical problems mentioned above. The organic compound provided in the embodiments of the present application can be used as an electron transport material to effectively improve the film forming performance of the electron transport layer, improve electron transport, promote charge transfer, and thus enhance device stability.

[0005] In a first aspect, an embodiment of the present application provides an organic compound, the structure of which is shown in Formula 1:

[0006]

[0007] Among them, R is

[0008] L1 is selected from a substituted or unsubstituted alkylene group having 1 to 5 carbon atoms;

[0009] Ar1 and Ar2 are the same or different and are independently selected from hydrogen, substituted or unsubstituted alkyl having 1 to 50 carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 50 carbon atoms, substituted or unsubstituted aryl having 6 to 50 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 50 carbon atoms, and at least one of Ar1 and Ar2 is selected from substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl; or Ar1, Ar2 and the carbon atoms to which they are connected form a ring structure;

[0010] In Ar1 and Ar2, the heteroatom in the heteroalkyl group is selected from N, O, S, and Si;

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

[0012] The substituents in L1, Ar1 and Ar2 are the same or different and are independently selected from a halogen group, a nitro group, a cyano group and a mercapto group.

[0013] In a second aspect, the present application provides a method for preparing any of the above organic compounds, comprising:

[0014] Using decacyclic olefin as raw material A, it reacts with 1-piperidinylcarbonyl chloride to undergo aminoacylation to obtain intermediate product B.

[0015]

[0016] Intermediate product B is hydrolyzed with hydrobromic acid to obtain intermediate product C.

[0017]

[0018] The intermediate product C undergoes a condensation reaction with a primary amine to obtain the final product D.

[0019]

[0020] In a third aspect, an embodiment of the present application provides an electron transport material comprising any of the above-mentioned organic compounds.

[0021] In a fourth aspect, an embodiment of the present application provides an electronic component, characterized in that it includes an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer contains any one of the above-mentioned organic compounds.

[0022] In a fifth aspect, an embodiment of the present application provides an electronic device comprising any of the electronic components described above.

[0023] The above technical solution adopted in the embodiment of the present application may have the following advantages:

[0024] The organic compound provided in the embodiment of the present application has decacyclic triimide (DTI) as a parent core and has three terminal substituents respectively connected to the three N ends of the parent core; the decacyclic triimide parent core has a three-dimensional core structure that can increase steric hindrance and effectively inhibit excessive molecular aggregation while maintaining a high electron mobility; by modifying the parent core with terminal substituents, the terminal substituents The decacyclic olefin triimide mother core has a larger conjugated plane, which makes it have a more matched LUMO energy level, and can effectively improve electron transport by increasing the π-extension degree; the terminal substituents can also regulate the interface energy level, increase the solubility of organic compounds in organic solvents, effectively improve the film-forming properties of the electron transport layer, facilitate the formation of a uniform and dense electron transport layer, promote charge transfer, and enhance device stability. BRIEF DESCRIPTION OF THE DRAWINGS

[0025] The drawings of the present application are not necessarily drawn to scale. It should be understood that these drawings only depict some embodiments disclosed in the present application and should not be considered as limiting the scope of the present application.

[0026] Figure 1 It is a schematic diagram of the structure of a perovskite solar cell provided in an embodiment of the present application.

[0027] Description of reference numerals:

[0028] 100, anode; 200, cathode; 300, functional layer; 310, hole transport layer; 320, perovskite light absorption layer; 330, electron transport layer; 340, cathode buffer layer. DETAILED DESCRIPTION

[0029] Embodiments of the present application will now be described more fully with reference to the accompanying drawings, examples of which are shown in the accompanying drawings. In the accompanying drawings, for clarity, the sizes of layers, regions, elements and their relative sizes may be exaggerated. Wherein the same or similar reference numerals throughout represent the same or similar elements or elements with the same or similar functions. The embodiments described with reference to the accompanying drawings are exemplary and are only used to explain the present application, and cannot be construed as limitations on the present application. It should be noted that, in the absence of conflict, the embodiments in the present application and the features in the embodiments can be combined with each other. The described features, structures or characteristics can be combined in one or more embodiments in any suitable manner. In the following description, many specific details are provided to provide a full understanding of the embodiments of the present application.

[0030] To facilitate those skilled in the art to understand the technical solutions provided in the embodiments of the present application, the relevant technologies are described below:

[0031] Currently, fullerenes and their derivatives are commonly used as organic electron transport materials, but they have problems such as high cost, single energy level tunability, and poor stability in air.

[0032] The applicant has learned that: non-fullerene small molecule materials - arylene diimine derivatives have a conjugated planar structure, usually have high thermal stability and chemical stability, low synthesis cost, good batch reproducibility, and multifunctional reaction sites that make them easy to modify, and are expected to replace fullerene as an electron transport material; however, non-fullerene small molecule materials - arylene diimine derivatives as electron transport materials, due to their strong π-π stacking tendency, lead to strong molecular aggregation, which greatly affects the morphology and transport performance of the film, thereby affecting the device performance.

[0033] In view of the above problems, the present application aims to provide an organic compound as an electron transport material, which is a decacyclic alkene triimide (DTI) as a parent core, and three terminal substituents are connected to the N-terminal of the parent core. With DTI as the parent core, the terminal substituents are modified by molecular structure adjustment, and the synthesis is simple and convenient for modification. The three-dimensional core structure of the decacyclic alkene triimide parent core can increase the steric hindrance, effectively inhibit the excessive aggregation of molecules, and maintain a high electron mobility; by modifying the parent core with terminal substituents, the decacyclic alkene triimide parent core has a larger conjugated plane, so that it has a more matching 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 the 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 device stability.

[0034] In this application, It refers to the position of bonding to other substituents or bonding positions.

[0035] In the present application, the description methods "each... independently is" and "... are independently" and "... are independently selected from" are interchangeable and should be understood in a broad sense. They can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or that in the same group, the specific options expressed by the same symbols do not affect each other. For example, "the substituents in L1, Ar1 and Ar2 are the same or different, and are independently selected from halogen groups, nitro groups, cyano groups, and mercapto groups", which means that the substituents in L1 can be the same 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 from each other; in short, the options of each substituent do not affect each other.

[0036] In the present application, the term "substituted or unsubstituted" means that the functional group recorded after the term may or may not have a substituent (hereinafter, for the convenience of description, the substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl or non-substituted aryl with a substituent Rc. The above-mentioned substituent, i.e., Rc, can be, for example, a halogen group, a nitro group, a cyano group, or a mercapto group. In the present application, the "substituted" functional group can be substituted by one or more substituents of the above-mentioned Rc; when two substituents Rc are connected to the same atom, the two substituents Rc can exist independently. The substituted alkyl can be one or more hydrogen atoms in the alkyl replaced by groups such as halogen groups, nitro groups, cyano groups, mercapto groups, etc. The substituted aryl can be one or more hydrogen atoms in the aryl replaced by groups such as halogen groups, nitro groups, cyano groups, mercapto groups, etc. The substituted heteroaryl can be one or more hydrogen atoms in the heteroaryl replaced by groups such as halogen groups, nitro groups, cyano groups, mercapto groups, etc.

[0037] In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to the total number of carbon atoms. For example, the number of carbon atoms of a substituted aryl group refers to 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 refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group. For example, if L1 is selected from a substituted alkylene group having 5 carbon atoms, the total number of carbon atoms of the alkylene group and the substituents on it is 5; if Ar1 is selected from a substituted aryl group having 20 carbon atoms, the total number of carbon atoms of the aryl group and the substituents on it is 20.

[0038] In the present application, when no specific definition is otherwise provided, "hetero" means including at least one heteroatom such as N, O, S, Si, etc. in one functional group and the remaining atoms are carbon and hydrogen.

[0039] In the present application, "alkyl" may include straight chain alkyl or branched chain alkyl. The "alkyl" of the present application may contain 1-50 carbon atoms, in some embodiments, the number of carbon atoms in the alkyl may be 1-30, in some embodiments, the number of carbon atoms in the alkyl may be 1-20, in other embodiments the number of carbon atoms in the alkyl may be 1-15, in other embodiments the number of carbon atoms in the alkyl may be 3-15, in other embodiments the number of carbon atoms in the alkyl may be 1-10. Of course, the number of carbon atoms in the alkyl may also be other numbers, for example, the number of carbon atoms in the alkyl may be 1, 2, 3, 4, 5, 6, 7, 8, 9 10 or 15. In a specific embodiment, the alkyl includes, but is not limited to, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, wherein the propyl group includes n-propyl and isopropyl, and the butyl group includes n-butyl, isobutyl, sec-butyl, and tert-butyl.

[0040] In the present application, the alkylene group refers to a divalent group formed by further losing a hydrogen atom from an alkyl group.

[0041] In the present application, an "alkylene group" may have 1 to 5 carbon atoms. In the present application, a numerical range such as "1 to 5" refers to each integer in the given range; for example, "1 to 5 carbon atoms" refers to an alkylene group that may contain 1 carbon atom, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, and 5 carbon atoms. In a specific embodiment, an alkylene group includes, but is not limited to, methylene, ethylene, propylene, isopropylene, n-butylene, isobutylene, sec-butylene, tert-butylene, and pentylene.

[0042] In the present application, "heteroalkyl" refers to an alkyl group in which 1, 2, 3, 4 or 5 carbon atoms are replaced by heteroatoms, and the heteroatoms may be at least one of O, N, Si, and S. The "heteroalkyl" of the present application may contain 3-50 carbon atoms. In some embodiments, the number of carbon atoms in the heteroalkyl group may be 3-30, in other embodiments, the number of carbon atoms in the heteroalkyl group may be 3-20, in other embodiments, the number of carbon atoms in the heteroalkyl group may be 3-15, and in other embodiments, the number of carbon atoms in the heteroalkyl group may be 1-10. Of course, the number of carbon atoms in the heteroalkyl group may also be other numbers. For example, the number of carbon atoms in the heteroalkyl group may be 1, 2, 3, 4, 5, 6, 7, 8, 10 or 15.

[0043] In the present application, "cycloalkyl" refers to 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 may contain 3-50 carbon atoms, and in some embodiments the number of carbon atoms in the cycloalkyl may be 3-30, in other embodiments the number of carbon atoms in the cycloalkyl may be 3-20, and in other embodiments the number of carbon atoms in the cycloalkyl may be 3-15. Of course, the number of carbon atoms in the cycloalkyl may also be other numbers, for example, the number of carbon atoms in the cycloalkyl may be 3, 4, 5, 6, 7, 8, 10, 12, 13 or 15.

[0044] In the present application, "aryl" refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl group. In other words, the aryl group can be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups connected by carbon-carbon bond conjugation, a monocyclic aryl group and a condensed ring aryl group connected by carbon-carbon bond conjugation, and two or more condensed ring aryl groups connected by carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups connected by carbon-carbon bond conjugation can also be regarded as the aryl group of the present application. The "aryl" of 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, and 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 aromatic group may also be other numbers. For example, the number of carbon atoms in the aromatic group may be 6, 7, 8, 9, 10, 12, 13, 14 or 15.

[0045] In the present application, "heteroaryl" refers to a monovalent aromatic ring or a derivative thereof containing 1, 2, 3, 4 or 5 heteroatoms in the ring, wherein the heteroatom may be at least one of O, N, Si and S. The "heteroaryl" of the present application may contain 3-50 carbon atoms, and in some embodiments, the number of carbon atoms in the heteroaryl may be 3-30, in other embodiments, the number of carbon atoms in the heteroaryl may be 3-20, and in other embodiments, the number of carbon atoms in the heteroaryl may be 3-15. Of course, the number of carbon atoms in the heteroaryl may also be other numbers, for example, the number of carbon atoms in the heteroaryl may be 3, 5, 6, 8, 10, 12, 13, 14 or 15.

[0046] In the present application, "forming a ring structure" means that two groups are connected to each other by a chemical bond and are optionally aromatized. In the present application, Ar1, Ar2 and the carbon atoms to which they are connected (the carbon atoms in L1) form a ring structure. In some embodiments, the number of carbon atoms in the ring structure is 3 to 8, and in other embodiments, the number of carbon atoms in the ring structure is 5 to 6; the ring structure includes but is not limited to cyclopropane, cyclobutane, cyclopentane, cyclohexane, and cycloheptane. In the present application, the ring structure formed by Ar1, Ar2 and the carbon atoms to which they are connected can be fused with a benzene ring, including but not limited to benzocyclopropane, benzocyclobutane, benzocyclopentane (e.g., ), benzocyclohexyl (eg, ), benzocycloheptanyl.

[0047] In the present application, the halogen group may include fluorine, iodine, bromine, chlorine, and the like.

[0048] The present invention provides an organic compound, the structure of which is shown in Formula 1:

[0049]

[0050] Among them, R is

[0051] L1 is selected from a substituted or unsubstituted alkylene group having 1 to 5 carbon atoms;

[0052] Ar1 and Ar2 are the same or different and are independently selected from hydrogen, substituted or unsubstituted alkyl having 1 to 50 carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 50 carbon atoms, substituted or unsubstituted aryl having 6 to 50 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 50 carbon atoms, and at least one of Ar1 and Ar2 is selected from substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl; or Ar1, Ar2 and the carbon atoms to which they are connected form a ring structure;

[0053] In Ar1 and Ar2, the heteroatom in the heteroalkyl group is selected from N, O, S, and Si;

[0054] In Ar1 and Ar2, the heteroatom in the heteroaryl group is selected from N, O, S, Si;

[0055] The substituents in L1, Ar1 and Ar2 are the same or different and are independently selected from a halogen group, a nitro group, a cyano group and a mercapto group.

[0056] In some optional embodiments, L1 is selected from substituted or unsubstituted methylene, substituted or unsubstituted ethylene, substituted or unsubstituted propylene, substituted or unsubstituted butylene;

[0057] The substituent in L1 is selected from F, Cl, Br, nitro, cyano, and mercapto.

[0058] In some optional embodiments, L1 is selected from methylene, ethylene, propylene, and butylene.

[0059] In some optional embodiments, Ar1 and Ar2 are the same or different, and are independently selected from hydrogen, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, at least one of Ar1 and Ar2 is selected from substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl; or Ar1 and Ar2 together with the carbon atoms to which they are connected form a cyclic structure with 3 to 8 carbon atoms.

[0060] In some optional embodiments, Ar1 and Ar2 are the same or different, and are independently selected from hydrogen, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, at least one of Ar1 and Ar2 is selected from substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl; or Ar1 and Ar2 together with the carbon atoms to which they are connected form a cyclic structure with 3 to 8 carbon atoms.

[0061] In some optional embodiments, L1 is selected from substituted or unsubstituted methylene, substituted or unsubstituted ethylene, substituted or unsubstituted propylene, substituted or unsubstituted butylene; the substituent in L1 is selected from cyano;

[0062] Ar1 and Ar2 are the same or different and are independently selected from hydrogen, substituted or unsubstituted alkyl having 1 to 8 carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 carbon atoms, substituted or unsubstituted aryl having 6 to 15 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 15 carbon atoms, and at least one of Ar1 and Ar2 is selected from substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl; or Ar1, Ar2, together with the carbon atoms to which they are attached, form a cyclic structure having 4 to 6 carbon atoms;

[0063] In Ar1 and Ar2, the heteroatom in the heteroalkyl group is selected from N, O, and S;

[0064] In Ar1 and Ar2, the heteroatom in the heteroaryl group is selected from N, O, and S;

[0065] The substituents in Ar1 and Ar2 are the same or different and are independently selected from a halogen group, a nitro group, and a cyano group.

[0066] In some embodiments, Ar1 and Ar2 are the same or different, and are independently selected from hydrogen, a substituted or unsubstituted W1 group, a substituted or unsubstituted W2 group, and at least one of Ar1 and Ar2 is selected from a substituted or unsubstituted W2 group; or Ar1, Ar2 and the carbon atoms to which they are attached form a ring structure;

[0067] Wherein, the W1 group is selected from methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and octyl;

[0068] The W2 group is selected from

[0069] When Ar1, Ar2 and the carbon atom to which they are attached form a ring structure, R is selected from

[0070] In some embodiments, R is selected from

[0071]

[0072] In some optional embodiments, when one of Ar1 and Ar2 is selected from a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, or a substituted or unsubstituted heteroalkyl group having 3 to 15 carbon atoms, and the other is selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, Ar1, Ar2 and the carbon atoms to which they are connected together form a ring structure. For example, Ar1, Ar2 and the carbon atoms to which they are connected (the carbon atoms in L1) together form a five-membered ring structure Or six-membered ring structure

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

[0074]

[0075]

[0076]

[0077]

[0078]

[0079] The present application provides a method for preparing an organic compound provided in any of the above embodiments, comprising:

[0080] Step S110: using decacyclic olefin as raw material A, and carrying out aminoacylation reaction with 1-piperidinylcarbonyl chloride to obtain intermediate product B.

[0081]

[0082] Step S120: The intermediate product B is subjected to a hydrolysis reaction with hydrobromic acid to obtain an intermediate product C.

[0083]

[0084] Step S130: The intermediate product C undergoes a condensation reaction with a primary amine to obtain a final product D.

[0085]

[0086] In some optional embodiments, the method for preparing the organic compound comprises:

[0087] Step S110: subjecting raw material A (decacyclic olefin) and 1-piperidinylcarbonyl chloride to an aminoacylation reaction in a mixed solution of AlCl3 and o-dichlorobenzene, the reaction temperature being 0°C-175°C, and the reaction time being 3-5 days at 175°C, to obtain decacyclic olefin-3,4,9,10,15,16-hexaylhexa(piperidin-1-ylmethanone) (i.e., intermediate product B).

[0088]

[0089] Step S120: reflux the intermediate product 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 trihydrogenate (i.e., intermediate product C).

[0090]

[0091] Step S130: the intermediate product C and the primary amine (R-NH2) are subjected to a condensation reaction in a suspension of N,N-dimethylformamide (DMF) at a reaction temperature of 90-140° C. for a reaction time of 12-28 hours to obtain NR-decacyclopentene-3,4,9,10,15,16-hexacarboxylic acid triimide (i.e., the final product D).

[0092]

[0093] 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 rather than to limit the scope of the present application in any way.

[0094]

Compound 1

[0095] The preparation method of compound 1 is:

[0096] Step S110: subjecting raw material A (decacyclic olefin) and 1-piperidinylcarbonyl chloride to an aminoacylation reaction in a mixed solution of AlCl3 and o-dichlorobenzene, the reaction temperature being 0°C-175°C, and the reaction time being 4 days at 175°C, to obtain decacyclic olefin-3,4,9,10,15,16-hexaylhexa(piperidin-1-ylmethanone) (i.e., intermediate product B).

[0097]

[0098] At 0°C, AlCl3 (2.8 g, 21.0 mmol) was added to a mixture of raw material A (decacyclic olefin) (0.75 g, 1.66 mmol), 1-piperidinecarbonyl 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-piperidinecarbonyl chloride (0.9 mL, 7.2 mmol) were added, and the mixture was stirred at 135°C overnight, 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 three times with chloroform (100 mL), and the organic phase was dried over NaSO4, filtered, and concentrated in vacuo. 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 celite. The filtrate was separated by column chromatography with an eluent (pure chloroform to acetone:chloroform = 3:20) to obtain intermediate B (0.89 g, 0.80 mmol, 48%) as a yellow solid.

[0099] The structural characterization parameters of intermediate product B are: 1 H NMR (500MHz, CDCl3): δ8.76(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 (125MHz, CDCl3): δ168.91,168.86,137.84,136.07,135.12,127.30,124.97,123.45,48.91,42.66,26.07,25.56,24.84; FDMS(m / z): [M + ]calcd.for C 72 H 72 N6O6, 1116.6; found, 1116.5.

[0100] Step S120: reflux the intermediate product B in a hydrobromic acid solution for 1 hour to obtain decene-3,4,9,10,15,16-hexacarboxylic acid trihydrogenate (i.e., intermediate product C).

[0101]

[0102] A suspension of 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 in vacuo at 80°C overnight to give intermediate product C (0.33 g, 0.50 mmol, 97%) as a red solid.

[0103] It should be noted that the intermediate product C obtained in step S120 can be directly used for the next reaction without further purification.

[0104] Step S130: The intermediate product C and the primary amine (1-phenylhexan-1-amine) are subjected to a condensation reaction 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). The yield of Compound 1 is 59%.

[0105]

[0106] Compounds 2 to 50 were prepared by referring to the synthesis method of compound 1, except that the primary amine in compound 1 was replaced by the reactant primary amine in Table 1.

[0107] Table 1 Compounds 1 to 50

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118] An embodiment of the present application provides an electron transport material, comprising an organic compound provided by any embodiment of the present application.

[0119] In some optional embodiments, the preparation method of the electron transport material includes: dissolving an organic compound in an organic solvent (such as chloroform), stirring and dissolving to obtain the electron transport material, wherein the mass volume ratio of the organic compound to the organic solvent is (1 to 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, and 20 mg / mL.

[0120] An embodiment of the present application provides an electronic component, including an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer contains an organic compound provided in any embodiment of the present application.

[0121] The organic compound provided in any embodiment of the present application can be used to form at least one of the multiple functional layers to improve the voltage characteristics, current characteristics, efficiency characteristics, etc. of the electronic component. In some optional embodiments, the functional layer includes an electron transport layer, and the electron transport layer includes the organic compound provided in any embodiment of the present application.

[0122] The electronic component provided in the embodiment of the present application may be a perovskite solar cell, a module or an organic light emitting diode. Figure 1 As shown, the perovskite solar cell includes an anode 100 and a cathode 200 that are arranged opposite to each other, and a functional layer 300 arranged between the anode 100 and the cathode 200; the functional layer 300 includes the organic compound provided in any embodiment of the present application.

[0123] In some optional embodiments, such as Figure 1 As shown, 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 disposed between the anode 100 and the perovskite light absorption layer 320, and the electron transport layer 330 is disposed between the perovskite light absorption layer 320 and the cathode 200. In some optional embodiments, such as Figure 1 As shown, the functional layer 300 further includes a cathode buffer layer 340 disposed between the electron transport layer 330 and the cathode 200. The electron transport layer 330 includes the organic compound provided in any embodiment of the present application.

[0124] For example, Figure 1As shown, the perovskite solar cell includes an anode 100, a hole transport layer 310, a perovskite light absorption layer 320, an electron transport layer 330, a cathode buffer layer 340 and a cathode 200 stacked in sequence. The electron transport layer 330 includes an organic compound provided in any embodiment of the present application.

[0125] 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 may include: placing the conductive substrate in an ultrasonic cleaning instrument, and ultrasonically cleaning it with deionized water, acetone, and isopropanol, respectively, and the cleaning time for each step is 10-30 minutes. The step of treating the conductive substrate with ozone may include: treating the conductive substrate with a UV-zone, wherein the treatment time is 2-10 minutes.

[0126] In some optional embodiments, the material of the hole transport layer includes nickel oxide (NiO X ), tin dioxide (SnO2), poly(bis(4-phenyl)(2,4,6-trimethylphenyl)amine) (PTAA), poly(3,4-ethylenedioxythiophene)-polystyrenesulfonic acid (PEDOT:PSS), [2-(9H-carbazole-9-yl)ethyl]phosphonic acid (2PACz), [2-(3,6-dimethoxy-9H-carbazole-9-yl)ethyl]phosphonic acid (MeO-2PACz), [4-(3,6-dimethyl-9H-carbazole-9-yl)butyl One or more of [N,N-di(4-methylphenyl)aniline] (TAPC). In an optional embodiment, the hole transport layer material is first added to a diluent for dilution, and then the hole transport layer is prepared by spin coating, vacuum evaporation, magnetron sputtering, atomic layer deposition, etc., wherein the diluent includes one or more of chlorobenzene, ethanol, and isopropanol.

[0127] In some optional embodiments, the preparation method of the perovskite light absorbing layer includes: coating a perovskite precursor solution on the hole transport layer by a slit coating method to form a perovskite light absorbing layer. In some optional embodiments, the perovskite precursor solution includes a perovskite material and an organic solvent, dissolving the perovskite material in the organic solvent to form a perovskite precursor solution, and after coating the perovskite precursor solution on the surface of the hole transport layer, the organic solvent is removed by a post-treatment process (e.g., a thermal annealing process, the annealing temperature is 100° C., and the annealing time is 40 min) to form a perovskite light absorbing layer including the perovskite material.

[0128] In some optional embodiments, the electron transport layer includes the organic compound provided in any embodiment of the present application to improve the electron transport performance of the electron transport layer. The electron transport layer may contain other materials or may not contain other materials. The preparation method of the electron transport layer includes: dissolving the organic compound provided in any embodiment of the present application in an organic solvent (such as chloroform), stirring and dissolving to obtain an electron transport material, and using a spin coating method to coat the electron transport material on the perovskite light absorption layer to obtain an electron transport layer. Among them, the spin coating speed can be 2500-3500rpm, specifically 3000rpm; the spin coating time can be 20-40s, specifically 30s.

[0129] In some optional embodiments, the material of the cathode buffer layer includes one or two 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 includes: dissolving the material of the cathode buffer layer in an organic solvent (such as ethanol), stirring and dissolving to obtain a cathode buffer material solution, and using a spin coating method to apply the cathode buffer material solution on the electron transport layer to obtain a cathode buffer layer.

[0130] In some optional embodiments, the cathode is an electrode, and the cathode material includes one of silver, copper, transparent conductive oxide (TCO), and carbon electrode. The cathode can be prepared by thermal evaporation, vacuum evaporation, sputtering, atomic layer deposition, etc. The thickness of the cathode can be 80-120nm.

[0131] The method for preparing the perovskite solar cell of the present application will be described in detail below in conjunction with the embodiments; however, the following description is used to explain the present application rather than to limit the scope of the present application in any way.

[0132] [Example 1]

[0133] like Figure 1 As shown, the specific structure of the perovskite solar cell in this embodiment is:

[0134] 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 are sequentially stacked.

[0135] The specific preparation process of the perovskite solar cell in this embodiment is as follows:

[0136] S210: Dissolve 10 mg of compound 1 in 1 mL of chloroform and stir at room temperature to obtain a uniform electron transport material;

[0137] S220: providing an anode 100;

[0138] S230: dissolving Me-4PACz in chlorobenzene to obtain a hole transport material solution, and dripping the hole transport material solution onto the upper surface of the anode 100 to form a hole transport layer 310;

[0139] S240: dissolving lead iodide and iodomethylamine solids in N,N-dimethylformamide (DMF), stirring until completely dissolved to obtain a perovskite precursor solution, and coating the perovskite precursor solution on the upper surface of the hole transport layer 310 to form a perovskite light absorption layer 320;

[0140] S250: using a spin coating method to coat an electron transport material on the upper surface of the perovskite light absorption layer 320 to form an electron transport layer 330;

[0141] S250: dissolving BCP in an ethanol solution to obtain a cathode buffer material solution with a mass volume ratio of 0.5 mg / mL, and coating the cathode buffer material solution on the upper surface of the electron transport layer 330 by spin coating to form a cathode buffer layer 340;

[0142] S270: forming a cathode 200 on the upper surface of the cathode buffer layer 340 by vacuum evaporation, wherein the thickness of the cathode 200 is 100 nm.

[0143] [Example 2-Example 50]

[0144] The perovskite solar cells of Examples 2 to 50 were prepared by referring to the preparation method of Example 1, except that Compound 1 was replaced with an equal mass of Compound 2, Compound 3, Compound 4, Compound 5, Compound 6, Compound 7, Compound 8, Compound 9, Compound 10, Compound 11, Compound 12, Compound 13, Compound 14, Compound 15, Compound 16, Compound 17, Compound 18, Compound 19, Compound 20, Compound 21, Compound 22, Compound 23, Compound 24, Compound 25, Compound 26, Compound 27, Compound 28, Compound 29, Compound 30, Compound 31, Compound 32, Compound 33, Compound 34, Compound 35, Compound 36, Compound 37, Compound 38, Compound 39, Compound 40, Compound 41, Compound 42, Compound 43, Compound 44, Compound 45, Compound 46, Compound 47, Compound 48, Compound 49 or Compound 50.

[0145] [Comparative Example 1]

[0146] The perovskite solar cell of Comparative Example 1 was prepared by referring to the preparation method of Example 1, except that S210 of Comparative Example 1 was: 10 mg of C 60 (Fullerene) was dissolved in 1 mL of chloroform and stirred at room temperature to obtain a uniform electron transport material.

[0147] The following is a performance test of the perovskite solar cells provided in Examples 1-50 of the present application and Comparative Example 1 to obtain the open circuit voltage, fill factor, short circuit current density, and photoelectric conversion efficiency of the corresponding battery devices. The test results are shown in Table 2.

[0148] Table 2 Performance test results of perovskite solar cells of Examples 1-50 and Comparative Example 1

[0149] From the data in Table 2, it can be seen that the devices prepared by Examples 1-50 of the present application and Comparative Example 1 were subjected to performance tests. Compared with Comparative Example 1, the open circuit voltage and short circuit current density of the perovskite solar cells of Examples 1-50 of the present application were slightly improved, and the fill factor and photoelectric conversion efficiency were significantly improved. This shows that the organic compounds of Examples 1-50 of the present application can effectively improve the film-forming properties 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.

[0152] In summary, the organic compound provided in the embodiment of the present application has decacyclic triimide (DTI) as the mother core and has three terminal substituents respectively connected to the three N ends of the mother core; the decacyclic triimide mother core has a three-dimensional core structure that can increase the steric hindrance and effectively inhibit the excessive aggregation of molecules, so that the high electron mobility is maintained while inhibiting the aggregation; by modifying the mother core with terminal substituents, the terminal substituents The decacyclic olefin triimide mother core has a larger conjugated plane, which makes it have a more matched LUMO energy level, and can also effectively improve electron transport by increasing the π-extension degree; the terminal substituents can also regulate the interface energy level, increase the solubility of organic compounds in organic solvents, and effectively improve the film-forming properties of the electron transport layer, making it easier to form a uniform and dense electron transport layer on functional layers such as the perovskite light absorbing layer, effectively reducing the direct contact between the functional layers such as the perovskite light absorbing layer and the cathode, promoting charge transfer, and improving device stability.

[0153] The present application also provides an electronic device (not shown), including the electronic component provided by any embodiment of the present application. Since the electronic device has any electronic component described in the above electronic component implementation, it has the same beneficial effects, and the present application will not repeat them here.

[0154] It should be noted that the terms "length", "width", "thickness", "up", "down", "front", "back", "left", "right", "vertical", "horizontal", "top", "bottom", "inside", "outside", etc. are only for the convenience of describing the present application and simplifying the description, and do not indicate or imply that the device or element referred to must have a specific orientation, be constructed and operated in a specific orientation, and therefore cannot be understood as a limitation on the present application. The orientation words "inside" and "outside" refer to the inside and outside relative to the outline of each component itself. For example, if the device in the accompanying drawings is inverted, the device described as "above other devices or structures" or "above other devices or structures" will be positioned as "below other devices or structures" or "below other devices or structures". Therefore, the exemplary term "above..." can include both "above..." and "below..." orientations. The device can also be positioned in other different ways (rotated 90 degrees or in other orientations), and the spatial relative descriptions used here are interpreted accordingly.

[0155] It should be noted that the terms "first", "second", etc. in the specification and claims of the present application and the above-mentioned drawings are used to distinguish similar objects, and are not necessarily used to describe a specific order or sequence. It should be understood that the terms used in this way can be interchangeable where appropriate, so that the embodiments of the present application described herein can be implemented in an order other than those illustrated or described herein, for example. In addition, the terms "including" and "having" and any of their variations are intended to cover non-exclusive inclusions, for example, a process, method, system, product or device that includes a series of steps or units is not necessarily limited to those steps or units that are clearly listed, but may include other steps or units that are not clearly listed or inherent to these processes, methods, products or devices.

[0156] It should also be noted that "one embodiment", "another embodiment", "embodiment", etc. mentioned in this application refer to the specific features, structures or characteristics described in conjunction with the embodiment included in at least one embodiment generally described in this application. The same expression appearing in multiple places in the specification does not necessarily refer to the same embodiment. Further, when describing a specific feature, structure or characteristic in conjunction with any embodiment, it is claimed that the realization of such feature, structure or characteristic in conjunction with other embodiments also falls within the scope of this application.

[0157] In the above embodiments, the description of each embodiment has its own emphasis. For parts that are not described in detail in a certain embodiment, reference can be made to the relevant descriptions of other embodiments.

[0158] It should also be noted that the above are only preferred embodiments of the present application, and the patent protection scope of the present application is not limited thereto. Any equivalent structure or equivalent process transformation made using the contents of the present application specification and drawings, or directly or indirectly used in other related technical fields, are also included in the patent protection scope of the present application.

Claims

1. An organic compound, characterized in that The structure of the organic compound is shown in Formula 1: Among them, R is L1 is selected from a substituted or unsubstituted alkylene group having 1 to 5 carbon atoms; Ar1 and Ar2 are the same or different and are independently selected from hydrogen, substituted or unsubstituted alkyl having 1 to 50 carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 50 carbon atoms, substituted or unsubstituted aryl having 6 to 50 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 50 carbon atoms, and at least one of Ar1 and Ar2 is selected from substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl; or Ar1, Ar2 and the carbon atoms to which they are connected form a ring structure; In Ar1 and Ar2, the heteroatom in the heteroalkyl group is selected from N, O, S, and Si; In Ar1 and Ar2, the heteroatom in the heteroaryl group is selected from N, O, S, Si; The substituents in L1, Ar1 and Ar2 are the same or different and are independently selected from a halogen group, a nitro group, a cyano group and a mercapto group.

2. The organic compound according to claim 1, characterized in that L1 is selected from substituted or unsubstituted methylene, substituted or unsubstituted ethylene, substituted or unsubstituted propylene, substituted or unsubstituted butylene; The substituent in L1 is selected from F, Cl, Br, nitro, cyano, and mercapto.

3. The organic compound according to claim 1, characterized in that Ar1 and Ar2 are the same or different and are independently selected from hydrogen, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and at least one of Ar1 and Ar2 is selected from substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl; or Ar1 and Ar2, together with the carbon atoms to which they are attached, form a ring structure having 3 to 8 carbon atoms.

4. The organic compound according to claim 1, characterized in that L1 is selected from substituted or unsubstituted methylene, substituted or unsubstituted ethylene, substituted or unsubstituted propylene, substituted or unsubstituted butylene; the substituent in L1 is selected from cyano; Ar1 and Ar2 are the same or different and are independently selected from hydrogen, substituted or unsubstituted alkyl having 1 to 8 carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 carbon atoms, substituted or unsubstituted aryl having 6 to 15 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 15 carbon atoms, and at least one of Ar1 and Ar2 is selected from substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl; or Ar1, Ar2, together with the carbon atoms to which they are attached, form a cyclic structure having 4 to 6 carbon atoms; In Ar1 and Ar2, the heteroatom in the heteroalkyl group is selected from N, O, and S; In Ar1 and Ar2, the heteroatom in the heteroaryl group is selected from N, O, and S; The substituents in Ar1 and Ar2 are the same or different and are independently selected from a halogen group, a nitro group, and a cyano group.

5. The organic compound according to claim 1, characterized in that Ar1 and Ar2 are the same or different and are independently selected from hydrogen, a substituted or unsubstituted W1 group, a substituted or unsubstituted W2 group, and at least one of Ar1 and Ar2 is selected from a substituted or unsubstituted W2 group; or Ar1, Ar2 and the carbon atoms to which they are attached form a ring structure; Wherein, the W1 group is selected from methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and octyl; The W2 group is selected from When Ar1, Ar2 and the carbon atom to which they are attached form a ring structure, R is selected from 6. The organic compound according to claim 1, characterized in that R is selected from 7. The organic compound according to claim 1, characterized in that The organic compound is selected from one of the following compounds:

8. A method for preparing an organic compound according to any one of claims 1 to 7, characterized in that: include: Using decacyclic olefin as raw material A, it reacts with 1-piperidinylcarbonyl chloride to undergo aminoacylation to obtain intermediate product B. Intermediate product B is hydrolyzed with hydrobromic acid to obtain intermediate product C. The intermediate product C undergoes a condensation reaction with a primary amine to obtain the final product D.

9. An electron transport material, characterized in that Contains the organic compound according to any one of claims 1 to 7.

10. An electronic component, characterized in that: The invention comprises an anode and a cathode which are arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer comprises the organic compound according to any one of claims 1 to 7.

11. The electronic component according to claim 10, characterized in that: The electronic component is a perovskite solar cell or an organic light emitting diode.

12. The electronic component according to claim 10, characterized in that: The functional layer includes an electron transport layer, and the electron transport layer contains the organic compound.

13. An electronic device, characterized in that: The electronic component comprises any one of claims 10 to 12.

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