Compound, composite material, thin film, and optoelectronic device comprising compound

Abstract

The invention discloses a compound, a composite material, a thin film and a photoelectric device containing the compound, the compound is a phenylalanine derivative, the compound comprises an amide group and an aromatic group, a metal oxide material can be modified and treated, the surface defect state of the metal oxide material can be effectively passivated, the agglomeration phenomenon is improved, and the photoelectric device has the advantages that the photoelectric device is stable in performance; and the amide group in the compound can form a hydrogen bond with the hydroxyl group on the surface of the metal oxide material, so that the negative influence of the compound on the conductivity of the metal oxide material is reduced or eliminated.

Description

Technical Field

[0001] The present application relates to the field of optoelectronic technologies, and particularly relates to a compound, a composite material, a thin film, and an optoelectronic device comprising the compound. Background Art

[0002] Metal oxides refer to compounds formed by the combination of metal elements and oxygen elements. After nanosizing metal oxides, due to their small size, large specific surface area, and many surface active centers, metal oxides exhibit small size effect, surface and interface effect, quantum dot size effect, and macroscopic quantum tunneling effect, and thus are widely used in batteries, optoelectronic devices, supercapacitors, energy storage devices, and magnetic devices.

[0003] Metal oxides have the characteristics of small size, large specific surface area, and defective states on the surface, and thus have good electrical conductivity. Due to the presence of many defective states on the surface of metal oxides, the phenomenon of "aggregation" is likely to occur in metal oxides. Passivating the surface defective states of metal oxides with ligand compounds can effectively improve the "aggregation" phenomenon. However, common ligand compounds (such as carboxylic acid compounds with C8 - C30 or amine compounds with C8 - C30) will cause a significant decrease in the electrical conductivity of metal oxides. Summary of the Invention

[0004] Aiming at the deficiencies of the prior art, the present application provides a compound, a composite material, a thin film, and an optoelectronic device comprising the compound.

[0005] In a first aspect, the present application provides a compound having a structure represented by the following general formula (I):

[0006]

[0007] In the general formula (I), R s , R t , R x and R y are each independently selected from hydrogen, deuterium, -NR z R m, halogen, hydroxyl, carboxyl, nitro, sulfonic acid group, mercapto, cyano, aldehyde group, amide group, unsubstituted or substituted by at least one substituent C1-C30 aliphatic chain hydrocarbon group, unsubstituted or substituted by at least one substituent C1-C30 aliphatic chain alkoxy group, unsubstituted or substituted by at least one substituent C3-C30 aliphatic cycloalkane group, unsubstituted or substituted by at least one substituent C3-C30 aliphatic heterocyclic hydrocarbon group, unsubstituted or substituted by at least one substituent aryl group with 6 to 30 ring atoms, unsubstituted or substituted by at least one substituent aryloxy group with 6 to 30 ring atoms, unsubstituted or substituted by at least one substituent heteroaryl group with 5 to 30 ring atoms, or unsubstituted or substituted by at least one substituent heteroaryloxy group with 5 to 30 ring atoms, or a combination of these groups; the heteroatoms in the aliphatic heterocyclic hydrocarbon group, the heteroaryl group and the heteroaryloxy group are each independently selected from one or more of N, S, O, P and Si, and the number of heteroatoms in the aliphatic heterocyclic hydrocarbon group, the heteroaryl group and the heteroaryloxy group are each independently selected from 1 to 20;

[0008] The substituent is independently selected from deuterium, -NR z R m , halogen, hydroxyl, carboxyl, nitro, sulfonic acid group, mercapto, cyano, aldehyde group, or amide group, or a combination of these groups;

[0009] R z and R m are each independently selected from hydrogen, deuterium, C1-C30 aliphatic chain hydrocarbon group, or aryl group with 6 to 30 ring atoms;

[0010] n1 is a positive integer selected from 1 to 5.

[0011] In a second aspect, the present application provides a method for preparing a compound, and the method for preparing the compound includes the following steps:

[0012] (A1) Performing a first amide coupling reaction on a first reaction system including phenylalanine and 2,3-diamino-3-oxopropionic acid to obtain intermediate 1;

[0013] (A2) Performing a substitution reaction on a second reaction system including the intermediate 1 and substance A to obtain intermediate 2; and

[0014] (A3) Performing a second amide coupling reaction on a third reaction system including the intermediate 2 and substance B to obtain the compound represented by the general formula (Ⅰ-1);

[0015] wherein, the intermediate 1 has the structure shown in the following formula (Ⅱ):

[0016]

[0017] The substance A has the structure shown in the following formula (III):

[0018]

[0019] In formula (III), X is selected from F, Cl, Br or I;

[0020] The intermediate 2 has the structure shown in the following formula (IV):

[0021]

[0022] The substance B has the structure shown in the following formula (V):

[0023] R1—NH2 (V).

[0024] In a third aspect, the present application provides a composite material, which includes a metal oxide material and the compound described in the first aspect, or a compound prepared by the preparation method of any one of the compounds described in the second aspect.

[0025] In a fourth aspect, the present application provides a thin film, the material of which includes a metal oxide material and the compound described in the first aspect, or a compound prepared by the preparation method of the compound described in the second aspect.

[0026] In a fifth aspect, the present application provides an optoelectronic device, including:

[0027] A first electrode and a second electrode which are oppositely arranged; and

[0028] A functional layer disposed between the first electrode and the second electrode;

[0029] Wherein, the material of the functional layer includes the compound described in the first aspect, a compound prepared by the preparation method of the compound described in the second aspect, or the composite material described in the third aspect, or the functional layer includes any one of the thin films described in the fourth aspect.

[0030] In a sixth aspect, the present application further provides an electronic device, which includes any one of the optoelectronic devices described in the fifth aspect.

[0031] The present application provides a compound, a composite material, a thin film and an optoelectronic device containing the compound, having the following technical effects:

[0032] The compound is a phenylalanine derivative. The compound contains an amide group and an aromatic group, can modify and process metal oxide materials, effectively passivate the surface defect states of the metal oxide materials, thereby improving the "agglomeration" phenomenon, and the amide group in the compound can form hydrogen bonds with the hydroxyl groups on the surface of the metal oxide materials, reducing or eliminating the negative impact of the compound on the conductivity of the metal oxide materials. Description of the Drawings

[0033] Combined with the drawings below, through a detailed description of the specific embodiments of the present application, the technical solutions and other beneficial effects of the present application will become obvious.

[0034] Figure 1 It is a schematic flowchart of a preparation method of a compound provided by an embodiment of the present application.

[0035] Figure 2 It is a schematic structural diagram of a first optoelectronic device provided by an embodiment of the present application.

[0036] Figure 3 It is a schematic structural diagram of a second optoelectronic device provided by an embodiment of the present application.

[0037] Figure 4 It is the nuclear magnetic resonance spectrum of the compound prepared in Compound Example 1.

[0038] Figure 5 It is the nuclear magnetic resonance spectrum of the compound prepared in Compound Example 2.

[0039] Figure 6 It is the nuclear magnetic resonance spectrum of the compound prepared in Compound Example 3.

[0040] Figure 7 It is the nuclear magnetic resonance spectrum of the compound prepared in Compound Example 4.

[0041] Figure 8 It is the nuclear magnetic resonance spectrum of the compound prepared in Compound Example 5.

[0042] Figure 9 It is the nuclear magnetic resonance spectrum of the compound prepared in Compound Example 6.

[0043] Figure 10 It is the nuclear magnetic resonance spectrum of the compound prepared in Compound Example 7.

[0044] The reference numerals are as follows:

[0045] 10: Optoelectronic device, 101: First electrode, 102: Second electrode, 103: Functional layer, 1031: Electron functional layer, 1032: Hole functional layer, 1033: Light-emitting layer, 10311: First sub-layer, 10312: Second sub-layer, 10321: Hole injection layer, 10322: Hole transport layer. Detailed implementation manners

[0046] The technical solutions in the embodiments of the present application will be clearly and completely described below with reference to the accompanying drawings in the embodiments of the present application. Obviously, the described embodiments are only a part of the embodiments of the present application, rather than all the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without creative efforts shall fall within the protection scope of the present application.

[0047] Unless otherwise defined, all professional and scientific terms used herein have the same meaning as those familiar to those skilled in the art. In addition, any methods and materials similar or equivalent to the described content can be applied to the present invention. The preferred methods and materials described herein are only for illustrative purposes and do not limit the content of the present application.

[0048] It should be noted that the description order of the following embodiments does not limit the preferred order of the embodiments. The various embodiments of the present application may exist in a range form. It should be understood that the description in a range form is only for convenience and simplicity, and should not be construed as a rigid limitation on the scope of the present invention; therefore, it should be considered that the described range description has specifically disclosed all possible sub-ranges and single values within that range. For example, it should be considered that the range description from 1 to 6 has specifically disclosed sub-ranges such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., and single numbers within the counted range, such as 1, 2, 3, 4, 5, and 6, which applies regardless of the range. In addition, whenever a numerical range is indicated herein, it means including any cited number (fraction or integer) within the indicated range.

[0049] In the present application, unless otherwise stated, the orientation terms such as "upper" and "lower" generally refer to the upper and lower in the actual use or working state of the optoelectronic device, specifically the drawing direction in the accompanying drawings; and "inner" and "outer" refer to the outline of the optoelectronic device. The terms first, second, third, etc. are only used as labels and do not impose numerical requirements or establish an order.

[0050] In this application, descriptions such as "Layer A is formed on one side of Layer B", "Layer A is formed on the side of Layer B away from Layer C", or similar descriptions can mean that Layer A is directly formed on one side of Layer B or on the side of Layer B away from Layer C, that is, Layer A is in direct contact with Layer B, or it can mean that Layer A is indirectly formed on one side of Layer B or on the side of Layer B away from Layer C, that is, other spacer structure layers can also be formed between Layer A and Layer B. Similarly, "Layer A is disposed on one side of Layer B", "Layer A is disposed on the side of Layer B away from Layer C" can mean that Layer A is in direct contact with Layer B, or it can mean that other spacer structure layers are also provided between Layer A and Layer B; "Layer A is disposed between Layer B and Layer C" can mean that Layer A is in direct contact with Layer B and Layer A is in direct contact with Layer C, or Layer A is in direct contact with Layer B and one or more spacer structure layers are provided between Layer A and Layer C, or one or more spacer structure layers are provided between Layer A and Layer B and one or more spacer structure layers are provided between Layer A and Layer C, or one or more spacer structure layers are provided between Layer A and Layer B and Layer A is in direct contact with Layer C.

[0051] The term "comprising" means "including but not limited to".

[0052] The term "and / or" is used to describe the association relationship of associated objects, indicating that three relationships can exist. For example, A and / or B can mean: A exists alone, A and B exist simultaneously, and B exists alone. Where A and B can be singular or plural.

[0053] The term "at least one (kind / individual)" means one (kind / individual) or more than one (kind / individual), and "more than one (kind / individual)" means two (kinds / individuals) or more than two (kinds / individuals). The term "at least one (kind / individual)", "at least one (kind / individual) below", or similar expressions refer to any combination of these items, including any combination of single (kind / individual) or plural (kinds / individuals). For example, "at least one (kind / individual) of a, b, or c" or "at least one (kind / individual) of a, b, and c" can both be expressed as: a, b, c, a - b (that is, a and b), a - c, b - c, or a - b - c, where a, b, and c can be single (kind / individual) or multiple (kinds / individuals) respectively.

[0054] The term "inert gas" refers to a class of gases with inactive chemical properties, including but not limited to one or more of nitrogen, helium, neon, argon, krypton, and xenon.

[0055] The term "aliphatic hydrocarbon group" refers to an aliphatic straight-chain hydrocarbon group or an aliphatic branched-chain hydrocarbon group. The "C1-C30 aliphatic hydrocarbon group" can be, for example, a straight-chain alkyl group having 1 to 30 carbon atoms, a straight-chain alkenyl group having 2 to 30 carbon atoms, a straight-chain alkynyl group having 2 to 30 carbon atoms, a branched-chain alkyl group having 3 to 30 carbon atoms, a branched-chain alkenyl group having 4 to 30 carbon atoms, or a branched-chain alkynyl group having 4 to 30 carbon atoms. The number of carbon atoms in the aliphatic hydrocarbon group can be, for example, 1 to 3, 1 to 5, 1 to 8, 1 to 10, 1 to 20, 2 to 5, 2 to 10, 3 to 6, 3 to 10, 4 to 8, 4 to 10, 8 to 20, 8 to 30, or 15 to 30, with examples being 1, 2, 5, 8, 10, 20, 30, or a value between any two of the foregoing values.

[0056] The term "alkoxy group" refers to a group with the general formula *-O-alkylene group, where * represents the bonding site and O represents an oxygen atom.

[0057] The term "alicyclic hydrocarbon group" refers to an aliphatic cyclic hydrocarbon group. The number of ring atoms in the "C3-C30 alicyclic hydrocarbon group" can be, for example, 3 to 5, 3 to 8, 3 to 10, 3 to 14, 3 to 20, 5 to 10, 8 to 20, 8 to 30, or 15 to 30, with examples being 3, 5, 6, 8, 10, 15, 20, 24, 28, 30, or a value between any two of the foregoing values. Suitable examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, or adamantyl.

[0058] The term "aliphatic heterocyclic hydrocarbon group" refers to a group in which at least one carbon atom in the aliphatic cyclic hydrocarbon group is replaced by a non-carbon atom, and the non-carbon atom can be one or more of N atom, O atom, S atom, Si atom, and P atom. The number of ring atoms in the "C3-C30 aliphatic heterocyclic hydrocarbon group" can be, for example, 3 to 5, 3 to 8, 3 to 10, 3 to 14, 3 to 20, 5 to 10, 8 to 20, 8 to 30, or 15 to 30, with examples being 3, 5, 6, 8, 10, 14, 20, 24, 28, 30, or a value between any two of the foregoing values.

[0059] The term "aryl" refers to an aromatic hydrocarbon group derived by removing one hydrogen atom from an aromatic ring compound, which can be a monocyclic aryl, a fused-ring aryl, or a polycyclic aryl. For a polycyclic ring system, at least one ring is an aromatic ring system. "An aryl having 6 to 30 ring atoms" can be an aryl having 6 to 20 ring atoms, an aryl having 6 to 18 ring atoms, an aryl having 6 to 16 ring atoms, an aryl having 6 to 14 ring atoms, or an aryl having 6 to 10 ring atoms. The number of ring atoms can be, for example, 6, 10, 12, 14, 16, 18, 20, 24, 26, 28, 30 or a value between any two of the foregoing values. Suitable examples include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl, tetraphenylenyl, fluorenyl, dinaphthylenyl, acenaphthylenyl and their derivatives. It can be understood that multiple aryl groups can also be interrupted by short non-aromatic units (e.g., <10% non-H atoms such as C, N or O atoms), such as acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aryl.

[0060] The term "aryloxy" refers to a group of the general formula *-O-aryl.

[0061] The term "heteroaryl" refers to a group in which at least one carbon atom in the aryl group is replaced by a non-carbon atom, and the non-carbon atom can be one or more of N atom, O atom, S atom, Si atom and P atom. "A heteroaryl having 5 to 30 ring atoms" can be a heteroaryl having 5 to 20 ring atoms, a heteroaryl having 5 to 18 ring atoms, a heteroaryl having 5 to 16 ring atoms, a heteroaryl having 5 to 14 ring atoms, a heteroaryl having 5 to 12 ring atoms, or a heteroaryl having 5 to 10 ring atoms. The number of ring atoms can be, for example, 5, 10, 12, 14, 18, 20, 24, 26, 28, 30 or a value between any two of the foregoing values. Suitable examples include, but are not limited to, thienyl, furyl, pyrrolyl, dioxolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofuryl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothienyl, furanopyrrolyl, furanofuryl, thienofuryl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, phthalazinyl, phenanthridinyl, peridinyl, quinazolinone, dibenzothienyl, dibenzofuryl or carbazolyl.

[0062] The term "heteroaryloxy" refers to a group of the general formula *-O-heteroaryl.

[0063] The term "amino" refers to a group with the general formula -NR’R”, where R’ and R” are each independently selected from, but not limited to, a hydrogen atom, a deuterium atom, a cyano group, an isocyano group, a nitro group, a halogen atom, a straight-chain alkyl group having 1 to 10 carbon atoms, a branched-chain alkyl group or a cycloalkyl group having 3 to 10 carbon atoms, an aliphatic cycloalkylene group having 3 to 10 ring atoms, a heteroaliphatic cyclic group having 3 to 10 ring atoms, an aromatic group having 6 to 14 ring atoms, a heteroaromatic group having 5 to 14 ring atoms, a silyl group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a trifluoromethyl group, and the above groups may further be substituted by substituents acceptable in the art.

[0064] An embodiment of the present application provides a compound having a structure represented by the following general formula (I):

[0065]

[0066] In general formula (I), R s , R t , R x and R y are each independently selected from hydrogen, deuterium, -NR z R m , a halogen, a hydroxyl group, a carboxyl group, a nitro group, a sulfonic acid group, a mercapto group, a cyano group, an aldehyde group, an amide group, an unsubstituted or at least one substituent-substituted C1-C30 aliphatic chain hydrocarbon group, an unsubstituted or at least one substituent-substituted C1-C30 aliphatic chain hydrocarbon oxy group, an unsubstituted or at least one substituent-substituted C3-C30 aliphatic cycloalkylene group, an unsubstituted or at least one substituent-substituted C3-C30 aliphatic heterocyclic hydrocarbon group, an unsubstituted or at least one substituent-substituted aryl group having 6 to 30 ring atoms, an unsubstituted or at least one substituent-substituted aryloxy group having 6 to 30 ring atoms, an unsubstituted or at least one substituent-substituted heteroaryl group having 5 to 30 ring atoms, or an unsubstituted or at least one substituent-substituted heteroaryloxy group having 5 to 30 ring atoms, or a combination of these groups; the heteroatoms in the aliphatic heterocyclic hydrocarbon group, the heteroaryl group, and the heteroaryloxy group are each independently selected from one or more of N, S, O, P, and Si, and the number of heteroatoms in the aliphatic heterocyclic hydrocarbon group, the heteroaryl group, and the heteroaryloxy group are each independently selected from 1 to 20;

[0067] The substituent is each independently selected from deuterium, -NR z R m , a halogen, a hydroxyl group, a carboxyl group, a nitro group, a sulfonic acid group, a mercapto group, a cyano group, an aldehyde group, or an amide group, or a combination of these groups;

[0068] R z and R m are each independently selected from hydrogen, deuterium, a C1-C30 aliphatic hydrocarbon group, or an aryl group having 6 to 30 ring atoms;

[0069] n1 is selected from positive integers from 1 to 5, and n1 is, for example, 1, 2, 3, 4, or 5.

[0070] In some embodiments of the present application, the compound has the structure shown by the following general formula (I-1):

[0071]

[0072] In general formula (I-1), R1 is selected from an unsubstituted or at least one first group-substituted C1-C30 aliphatic hydrocarbon group, an unsubstituted or at least one first group-substituted C1-C30 aliphatic hydrocarbon oxy group, an unsubstituted or at least one first group-substituted C3-C30 aliphatic cyclo hydrocarbon group, an unsubstituted or at least one first group-substituted C3-C30 aliphatic heterocyclic hydrocarbon group, an unsubstituted or at least one first group-substituted aryl group having 6 to 30 ring atoms, an unsubstituted or at least one first group-substituted aryloxy group having 6 to 30 ring atoms, an unsubstituted or at least one first group-substituted heteroaryl group having 5 to 30 ring atoms, an unsubstituted or at least one first group-substituted heteroaryloxy group having 5 to 30 ring atoms, or a combination of these groups. The heteroatoms in the aliphatic heterocyclic hydrocarbon group, the heteroaryl group, and the heteroaryloxy group are each independently selected from one or more of N, S, O, P, and Si. The number of heteroatoms in the aliphatic heterocyclic hydrocarbon group, the heteroaryl group, and the heteroaryloxy group are each independently selected from 1 to 20. Each occurrence of the first group is independently selected from hydrogen, deuterium, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid group, aldehyde group, mercapto group, or cyano group.

[0073] In some embodiments of the present application, R1 is selected from an unsubstituted or at least one first group-substituted C8-C30 aliphatic hydrocarbon group, an unsubstituted or at least one first group-substituted C8-C30 aliphatic hydrocarbon oxy group, an unsubstituted or at least one first group-substituted C8-C30 alicyclic hydrocarbon group, an unsubstituted or at least one first group-substituted C8-C30 aliphatic heterocyclic hydrocarbon group, an unsubstituted or at least one first group-substituted aryl group having 6 to 20 ring atoms, an unsubstituted or at least one first group-substituted aryloxy group having 6 to 20 ring atoms, an unsubstituted or at least one first group-substituted heteroaryl group having 5 to 20 ring atoms, an unsubstituted or at least one first group-substituted heteroaryloxy group having 5 to 20 ring atoms, or a combination of these groups. For example, R1 is selected from an unsubstituted C8-C30 aliphatic hydrocarbon group, an unsubstituted C8-C30 aliphatic hydrocarbon oxy group, an unsubstituted C8-C30 alicyclic hydrocarbon group, an unsubstituted C8-C30 aliphatic heterocyclic hydrocarbon group, an unsubstituted aryl group having 6 to 20 ring atoms, an unsubstituted aryloxy group having 6 to 20 ring atoms, an unsubstituted heteroaryl group, and an unsubstituted heteroaryloxy group having 5 to 20 ring atoms.

[0074] In order to improve the hydrophobicity of the compound having the structure shown in the general formula (I-1), in some embodiments of the present application, R1 is selected from an unsubstituted or at least one first group-substituted C15-C30 aliphatic hydrocarbon group. It can be understood that the hydrophobicity of the compound can be adjusted by adjusting the number of carbon atoms in the aliphatic hydrocarbon group.

[0075] The embodiments of the present application also provide a method for preparing a compound, which can be used to prepare the compound having the structure shown in the general formula (I-1) above, such as Figure 1 shown, the method for preparing the compound includes the following steps:

[0076] (A1) Performing a first amide coupling reaction on a first reaction system including phenylalanine and 2,3-diamino-3-oxopropionic acid to obtain intermediate 1;

[0077] (A2) Performing a substitution reaction on a second reaction system including intermediate 1 and substance A to obtain intermediate 2;

[0078] (A3) Performing a second amide coupling reaction on a third reaction system including intermediate 2 and substance B to obtain the compound.

[0079] Specifically, the first reaction system further includes a first catalyst, and the first catalyst includes 1-hydroxybenzotriazole (abbreviated as HOBt, CAS No. 123333-53-9) and 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (abbreviated as EDCl, CAS No. 25952-53-8). In addition, the first reaction system further includes a solvent, and the solvent is, for example, selected from one or more of dichloromethane (abbreviated as DCM) and N,N-dimethylformamide (abbreviated as DMF). It can be understood that the reaction product obtained from the first amide coupling reaction is purified in one or more steps to improve the purity of Intermediate 1, and the purification process includes, but is not limited to, one or more of vacuum distillation, extraction, and drying.

[0080] The synthesis route of step (A1) is as follows:

[0081]

[0082] In order to balance the yield and purity of Intermediate 1, in some embodiments of the present application, the molar ratio of phenylalanine to 2,3-diamino-3-oxopropionic acid is 1:(1.0 - 1.5), for example, it can be 1:1, 1:1.1, 1:1.2, 1:1.3, 1:1.4, 1:1.5 or a value between any two of the foregoing ratios.

[0083] In order to ensure that the first amide coupling reaction has a good reaction rate and substrate conversion rate, and to avoid wasting the first catalyst, in some embodiments of the present application, the molar ratio of phenylalanine to the first catalyst is 1:(0.6 - 0.8), for example, it can be 1:0.6, 1:0.7, 1:0.8 or a value between any two of the foregoing ratios; and / or, the molar ratio of HOBt to EDCl in the first catalyst is 1:(1 - 1.1), for example, it can be 1:1, 1:1.02, 1:05, 1:1.07, 1:1.1 or a value between any two of the foregoing ratios.

[0084] In order to further balance the yield and purity of Intermediate 1, in some embodiments of the present application, the first amide coupling reaction is carried out in an inert gas atmosphere and at 20°C - 25°C, and the reaction time of the first amide coupling reaction is 10h - 20h.

[0085] In step (A2), the second reaction system further includes a solvent, which is selected from one or more of dichloromethane and N,N-dimethylformamide, for example. In addition, the second reaction system further includes an acid-binding agent, which can be an organic base or an inorganic base. Among them, the organic base includes but is not limited to one or more of triethylamine, N,N-diisopropylethylamine, and pyridine, and the inorganic base includes but is not limited to one or more of sodium acetate, sodium carbonate, potassium carbonate, sodium bicarbonate, and potassium bicarbonate. It can be understood that the reaction product obtained from the substitution reaction is purified in one or more steps to improve the purity of intermediate 2, and the purification processes include but are not limited to one or more of vacuum distillation, extraction, and drying.

[0086] The synthetic route of step (A2) is as follows:

[0087]

[0088] For substance A, X is selected from F, Cl, Br, or I.

[0089] In order to balance improving the yield and purity of intermediate 2, in some embodiments of the present application, the molar ratio of intermediate 1 to substance A is 1:(0.1 - 0.3), for example, it can be 1:0.1, 1:0.2, 1:0.3, or a value between any two of the foregoing ratios.

[0090] In order to further balance improving the yield and purity of intermediate 2, in some embodiments of the present application, the substitution reaction is carried out in an inert gas atmosphere and at 60°C - 70°C, and the reaction time of the substitution reaction is 10h - 12h.

[0091] In order to further balance improving the yield and purity of intermediate 2 and avoid wasting the acid-binding agent, in some embodiments of the present application, the molar ratio of intermediate 1 to the acid-binding agent is 1:(0.5 - 0.7).

[0092] In step (A3), the third reaction system further includes a second catalyst, and the second catalyst includes 1-hydroxybenzotriazole (abbreviated as HOBt, CAS number 123333-53-9) and 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (abbreviated as EDCl, CAS number 25952-53-8). In addition, the third reaction system further includes a solvent, which is selected from one or more of dichloromethane (abbreviated as DCM) and N,N-dimethylformamide (abbreviated as DMF), for example. It can be understood that the reaction product obtained from the second amide coupling reaction is purified in one or more steps to improve the purity of the compound of the structure shown in formula (I), and the purification processes include but are not limited to one or more of vacuum distillation, extraction, and drying.

[0093] The synthetic route of step (A3) is as follows:

[0094]

[0095] In order to balance the improvement of the yield and purity of the compound represented by the general formula (I-1), in some embodiments of the present application, the molar ratio of intermediate 2 to substance B is 1:(1.0-1.2), for example, 1:1, 1:1.1, 1:1.2 or a value between any two of the foregoing ratios.

[0096] In order to ensure that the second amide coupling reaction has a good reaction rate and substrate conversion rate, and to avoid wasting the second catalyst, in some embodiments of the present application, the molar ratio of intermediate 2 to the second catalyst is 1:(0.6-0.8); and / or, the molar ratio of HOBt to EDCl in the second catalyst is 1:(1-1.1).

[0097] In order to further balance the improvement of the yield and purity of the compound represented by the general formula (I-1), in some embodiments of the present application, the second amide coupling reaction is carried out in an inert gas atmosphere and at 20°C to 25°C, and the reaction time of the second amide coupling reaction is 10 h to 12 h.

[0098] The applicant has found that there are many surface defect states in metal oxides, which leads to a decrease in the binding energy between metal ions and the crystal lattice, resulting in the problem that metal ions are easily detached, leading to poor chemical stability and photothermal stability of metal oxides. And under the erosion of external water and oxygen, metal oxides are prone to the problem of "agglomeration", which has a negative impact on the performance of metal oxides.

[0099] Based on this, the embodiments of the present application provide a composite material, which includes a metal oxide material and a compound as described in any one of the foregoing, or a compound prepared by the preparation method of any one of the foregoing compounds.

[0100] In the composite material of the embodiments of the present application, the compound contains an amide group and an aromatic group, can modify the metal oxide material, effectively passivate the surface defect states of the metal oxide material, thereby improving the "agglomeration" phenomenon, and the amide group in the compound can form hydrogen bonds with the hydroxyl groups on the surface of the metal oxide material, reducing or eliminating the negative impact of the compound on the conductivity of the metal oxide material.

[0101] In some embodiments of the present application, the composite material is composed of the metal oxide material and the compound.

[0102] In some embodiments of the present application, in order to further improve the conductivity of the composite material, the proportion of the mass of the compound in the total mass of the composite material is 0.5% to 1.5%, for example, it can be 0.5%, 0.8%, 1%, 1.5% or a value between any two of the foregoing values.

[0103] In some embodiments of the present application, the metal oxide material includes at least one undoped first metal oxide and / or at least one doped second metal oxide. The first metal oxide is selected from ZnO, TiO2, SnO2, BaO, Ta2O3, Al2O3 or ZrO2, and / or the second metal oxide is a first metal oxide doped with a first doping element. The first doping element is selected from one or more of Mg, Ca, Zr, W, Ga, Li, Al, Ti, Y, In and Sn. The proportion of the molar amount of the first doping element in the total molar amount of the second metal oxide does not exceed 50%, for example, does not exceed 5%, does not exceed 10%, does not exceed 20%, does not exceed 30% or does not exceed 40%. The doped second metal oxide includes, but is not limited to, one or more of magnesium zinc oxide, calcium zinc oxide, zirconium zinc oxide, gallium zinc oxide, aluminum zinc oxide, lithium zinc oxide, titanium zinc oxide, yttrium zinc oxide, indium tin oxide and lithium titanium oxide. For example, it is Zn (1-x) Mg x O, Zn (1-x) Ca x O, Zn (1-x) Zr x O, Zn (1-x) W x O, Zn (1-x) Y x O, Zn (1-x) Ga x O, Zn (1-x) Al x O, Zn (1-x) Li x O, Al (1-x) Zn x O, Zn (1-x) Ti x O, Zn (1-x) Y x O, In (1-x) Sn x O and Ti (1-x) Li x O, and one or more of them, where 0 < x ≤ 0.5.

[0104] In the composite material, the metal oxide material can be one or more of nano-sheet shape, nano-rod shape, nano-needle shape or nano-particle shape. In some embodiments of the present application, the metal oxide material is in the form of nano-particles, and the average particle size of the metal oxide material is 2 nm to 15 nm.

[0105] In some embodiments of the present application, the amide group in the compound forms a hydrogen bond with the hydroxyl group on the surface of the metal oxide material, and / or the hydrogen atom of the aromatic group in the compound is coordinately bonded to the metal ion in the metal oxide material.

[0106] The embodiments of the present application also provide a thin film. The material of the thin film includes a metal oxide material and a compound as described in any one of the foregoing, or a compound prepared by the preparation method of any one of the foregoing compounds. The metal oxide material is referred to the foregoing description.

[0107] In the thin film of the embodiments of the present application, the compound has an amide group and an aromatic group. First, R1 of the compound can be selected from a hydrophobic group (such as a C8-C30 aliphatic hydrocarbon group), thereby improving the hydrophobicity of the thin film, effectively improving the problem of "agglomeration" of the metal oxide material due to water and oxygen erosion, and reducing the surface roughness of the thin film; Second, the hydrogen atom on the aromatic group of the compound can be coordinated with the metal ion in the metal oxide material, thereby inhibiting the shedding of the metal ion; Third, there is a Π-Π stacking interaction between the molecules of the compound, which can form a three-dimensional network structure, thereby binding the metal ion in the network structure and further inhibiting the shedding and migration of the metal ion; Fourth, the amide group in the compound can form a hydrogen bond with the hydroxyl group on the surface of the metal oxide material, reducing or eliminating the negative impact of the compound on the conductivity of the metal oxide material, so that the thin film has good conductivity.

[0108] In some embodiments of the present application, the material of the thin film consists of a metal oxide material and the compound.

[0109] In some embodiments of the present application, the average thickness of the thin film is 20 nm to 100 nm.

[0110] In order to further balance the improvement of the conductivity of the thin film and the reduction of the surface roughness of the thin film, in some embodiments of the present application, the thin film is a single-layer structure, and the mass ratio of the compound in the total mass of the thin film is 0.5% to 1.5%, such as 0.5%, 0.8%, 1%, 1.5% or any value between the foregoing two values.

[0111] In order to further balance the improvement of the conductivity of the thin film and the reduction of the surface roughness of the thin film, in some other embodiments of the present application, the thin film includes a first sub-layer and a second sub-layer arranged in a stacked manner. Among them, the material of the first sub-layer includes a metal oxide material, and an example of the material of the first sub-layer is a metal oxide material; the material of the second sub-layer includes the compound, and the thickness ratio of the second sub-layer to the first sub-layer is 1:(1.5 - 5), examples being 1:1.5, 1:2, 1:3, 1:4, 1:5 or a value between any two of the foregoing ratios; the average thickness of the first sub-layer is, for example, 10 nm to 90 nm, and / or the average thickness of the second sub-layer is, for example, 5 nm to 15 nm.

[0112] It should be noted that regardless of whether the thin film is a single-layer structure or a multi-layer structure, the thin film can be prepared by a solution method. For example, when the thin film is a single-layer structure, the preparation method of the thin film includes the steps of: depositing a solution containing a metal oxide material and the compound, and then performing a drying treatment to solidify into a film to obtain the thin film; another example is that the thin film is composed of a first sub-layer and a second sub-layer arranged in a stacked manner, and the preparation method of the thin film includes the steps of: depositing a solution containing a metal oxide material, and then performing a drying treatment to solidify into a film to obtain the first sub-layer; and, depositing a solution containing the compound on one side of the first sub-layer, and then performing a drying treatment to solidify into a film to obtain the second sub-layer. It can be understood that the second sub-layer can also be prepared first and then the first sub-layer can be formed on one side of the second sub-layer.

[0113] The embodiments of the present application also provide an optoelectronic device, and the optoelectronic device includes, but is not limited to, a light-emitting device, a photovoltaic cell or a photodetector, such as Figure 2 and Figure 3 As shown, the optoelectronic device 10 includes a first electrode 101, a second electrode 102 and a functional layer 103, and the functional layer 103 is disposed between the first electrode 101 and the second electrode 102. Among them, the material of the functional layer 103 includes any one of the compounds described above, a compound prepared by the preparation method of any one of the compounds described above, or a composite material described above, or the functional layer 103 includes any one of the thin films described above.

[0114] In the optoelectronic device 10 of the embodiments of the present application, the material of the functional layer 103 includes the compound, which can reduce or eliminate the negative impact on the performance of the optoelectronic device 10 caused by external water and oxygen erosion, improve the device efficiency and device life of the optoelectronic device 10, and is beneficial to improving the performance stability of the optoelectronic device 10.

[0115] In some embodiments of the present application, the materials of the first electrode 101 and the second electrode 102 are independently selected from one or more of metals, carbon materials, and third metal oxides. Among them, the metals include, but are not limited to, one or more of Al, Ag, Cu, Mo, Au, Ba, Pt, Ca, Ir, Ni, and Mg. The carbon materials include, but are not limited to, one or more of graphite, carbon nanotubes, graphene, and carbon fibers. The third metal oxide can be doped or undoped. The doped third metal oxides include, but are not limited to, one or more of indium tin oxide (ITO), fluorine-doped tin oxide (FTO), antimony tin oxide (ATO), aluminum-doped zinc oxide (AZO), gallium-doped zinc oxide (GZO), indium-doped zinc oxide (IZO), and magnesium-doped zinc oxide (MZO). The undoped third metal oxides include, but are not limited to, one or more of TiO2, SnO2, ZnO, and In2O3.

[0116] In some embodiments of the present application, continue to refer to Figure 2 and Figure 3 , the functional layer 103 includes an electronic functional layer 1031. The material of the electronic functional layer 1031 includes a compound as described in any one of the foregoing, a compound prepared by the preparation method of any one of the foregoing compounds, or a composite material as described in any one of the foregoing, or the electronic functional layer 1031 includes a thin film as described in any one of the foregoing. In the electronic functional layer 1031, the compound can modify the metal oxide material, inhibit the shedding and migration of metal ions, and effectively improve the problem of "agglomeration" of the metal oxide material due to water and oxygen erosion. In addition, the amide group in the compound can form a hydrogen bond with the hydroxyl group on the surface of the metal oxide material, reducing or eliminating the negative impact of the compound on the electron transport performance of the metal oxide material, thereby improving the performance stability of the electronic functional layer 1031, and further enhancing the optoelectronic performance and device life of the optoelectronic device 10.

[0117] It should be noted that the electronic functional layer 1031 can be a single-layer structure or a multi-layer structure, and the thickness of the electronic functional layer 1031 is, for example, 10 nm to 100 nm. When the electronic functional layer 1031 is a multi-layer structure, the electronic functional layer 1031 includes, for example, one or more of an electron injection layer, an electron transport layer, and a hole blocking layer. For the electronic functional layer 1031 including an electron injection layer, an electron transport layer, and a hole blocking layer, the electron transport layer is located between the electron injection layer and the hole blocking layer. One of the first electrode 101 and the second electrode 102 is an anode and the other is a cathode, and the electron injection layer is closer to the cathode than the hole blocking layer. For the electronic functional layer 1031 including an electron transport layer and a hole blocking layer, the electron transport layer is closer to the cathode than the hole blocking layer. For the electronic functional layer 1031 including an electron injection layer and an electron transport layer, the electron injection layer is closer to the cathode than the electron transport layer. When the electronic functional layer 1031 is a multi-layer structure, the material of one layer, some layers, or all layers thereof may include a compound as described in any one of the foregoing, or a compound prepared by the preparation method of any one of the foregoing compounds, or one layer, some layers, or all layers are a thin film as described in any one of the foregoing. As an example, the material of the electron transport layer includes a compound as described in any one of the foregoing, or a compound prepared by the preparation method of any one of the foregoing compounds, or the electron transport layer is a thin film as described in any one of the foregoing.

[0118] In some embodiments of the present application, the optoelectronic device 10 is a light-emitting device. One of the first electrode 101 and the second electrode 102 is an anode and the other is a cathode. The functional layer 103 includes a light-emitting layer 1033. For the optoelectronic device 10 including the light-emitting layer 1033 and the electronic functional layer 1031, the light-emitting layer 1033 is closer to the anode than the electronic functional layer 1031. For example, continuing to refer to Figure 2 and Figure 3 , the optoelectronic device 10 is a normal structure, the first electrode 101 is an anode and the second electrode 102 is a cathode. In the linear direction from the first electrode 101 to the second electrode 102, the light-emitting layer 1033 and the electronic functional layer 1031 are arranged in sequence.

[0119] Among them, the material of the light-emitting layer 1033 includes one or more of an organic light-emitting material and light-emitting quantum dots. Among them, the organic light-emitting material includes, but is not limited to, 4,4'-bis(N-carbazolyl)-1,1'-biphenyl: tris[2-(p-tolyl)pyridineiridium(III), 4,4',4”-tris(carbazol-9-yl)triphenylamine: tris[2-(p-tolyl)pyridineiridium, diarylanthracene derivatives, stilbene aromatic derivatives, pyrene derivatives, fluorene derivatives, TBPe fluorescent material, TTPX fluorescent material, TBRb fluorescent material, DBP fluorescent material, delayed fluorescence material, TTA material, thermally activated delayed material, polymer containing B-N covalent bond, hybrid local charge transfer excited state material, exciplex luminescent material, polyacetylene and its derivatives, poly(p-phenylene) and its derivatives, polythiophene and its derivatives, polyfluorene and its derivatives, etc., one or more of them.

[0120] The light-emitting quantum dots include, but are not limited to, one or more of red quantum dots, green quantum dots, and blue quantum dots, and the light-emitting quantum dots include, but are not limited to, one or more of single-component quantum dots, core-shell structure quantum dots, inorganic perovskite quantum dots, organic perovskite quantum dots, and organic-inorganic hybrid perovskite quantum dots. The core-shell structure quantum dots include one or more shell layers. The average particle size of the light-emitting quantum dots can be 2 nm to 20 nm, for example, it can be 2 nm, 4 nm, 6 nm, 8 nm, 10 nm, 12 nm, 15 nm, 20 nm, or a value between any two of the foregoing values.

[0121] For single-component quantum dots and core-shell quantum dots, the material of the single-component quantum dots, the material of the core of the core-shell quantum dots, or the material of the shell of the core-shell quantum dots includes, but is not limited to, at least one of II-VI group compounds, III-V group compounds, III-VI group compounds, IV-VI group compounds, or I-III-VI group compounds. Among them, the II-VI group compounds are selected from one or more of CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and HgZnSTe; the III-V group compounds are selected from one or more of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, and InAlPSb; the III-VI group compounds are selected from one or more of In2S3, In2Se3, InGaS3, and InGaSe3; the IV-VI group compounds are selected from one or more of SnS, SnSe, SnTe, PbS, PbSe, PbTe, SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, SnPbSSe, SnPbSeTe, and SnPbSTe; the I-III-VI group compounds are selected from one or more of AgInS, AgInS2, CuInS, CuInS2, AgGaS2, CuGaS2, CuGaO2, AgGaO2, AgAlO2, AgInGaS2, and CuInGaS2.It should be noted that for the materials of the aforementioned single-component quantum dots, or the cores of core-shell quantum dots, or the shells of core-shell quantum dots, the chemical formulas provided only indicate the elemental composition and do not indicate the content of each element. For example, CdZnSe only indicates that it is composed of three elements, Cd, Zn, and Se. If the content of each element is to be expressed, it corresponds to Cd. x Zn 1-x Se, 0 < x < 1.

[0122] For inorganic perovskite quantum dots, the general structural formula of inorganic perovskite quantum dots is AMX3, where A is Cs + , M is a divalent metal cation, and M includes but is not limited to Pb 2+ , Sn 2+ , Cu 2+ , Ni 2+ , Cd 2+ , Cr 2+ , Mn 2+ , Co 2+ , Fe 2+ , Ge 2+ , Yb 2+ or Eu 2+ , and X is a halogen anion, including but not limited to Cl - , Br - or I - .

[0123] For organic perovskite quantum dots, the general structural formula of organic perovskite quantum dots is CMX3, where C is formamidinium, M is a divalent metal cation, and M includes but is not limited to Pb 2+ , Sn 2+ , Cu 2+ , Ni 2+ , Cd 2+ , Cr 2+ , Mn 2+ , Co 2+ , Fe 2+ , Ge 2+ , Yb 2+ or Eu 2+ , and X is a halogen anion, including but not limited to Cl - , Br - or I - .

[0124] For organic-inorganic hybrid perovskite quantum dots, the general structural formula of organic-inorganic hybrid perovskite quantum dots is BMX3, where B is selected from organic amine cations, and organic amine cations include but are not limited to CH3(CH2) n-2 NH 3+ (n ≥ 2) or NH3(CH2) nNH3 2+ (n≥2), M is a divalent metal cation, and M includes but is not limited to Pb 2+ 、Sn 2+ 、Cu 2+ 、Ni 2+ 、Cd 2+ 、Cr 2+ 、Mn 2+ 、Co 2+ 、Fe 2+ 、Ge 2+ 、Yb 2+ or Eu 2+ ,X is a halogen anion, including but not limited to Cl - 、Br - or I - 。

[0125] It should be noted that when the material of the light-emitting layer 1033 includes light-emitting quantum dots, ligands can also be connected to the surface of the light-emitting quantum dots. The ligands include but are not limited to fatty carboxylic acid ligands with C1 - C 30 , aromatic carboxylic acid ligands with C6 - C 30 , fatty thiol ligands with C1 - C 30 , thiol aromatic ligands with C6 - C 30 , fatty amine ligands with C1 - C 30 , aromatic amine ligands with C6 - C 30 , fatty phosphine ligands with C1 - C 30 , aromatic phosphine ligands with C6 - C 30 and aromatic phosphate ligands with C6 - C 30 and one or more of halogen ligands.

[0126] Among them, the fatty carboxylic acid ligands with C1 - C 30 include but are not limited to one or more of octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanoic acid, eicosanoic acid, tetracosanoic acid, hexacosanoic acid, oleic acid, linoleic acid, arachidic acid, arachidonic acid, erucic acid, and docosahexaenoic acid; the aromatic carboxylic acid ligands with C6 - C 30 include but are not limited to one or more of benzoic acid, dibenzoic acid, and 1-naphthoic acid. The fatty thiol ligands with C1 - C 30 include but are not limited to one or more of hexanethiol, octanethiol, nonanethiol, decanethiol, undecanethiol, dodecanethiol, hexadecanethiol, and octadecanethiol, and the thiol aromatic ligands with C6 - C 30 include but are not limited to one or more of benzenethiol, triphenylmethanethiol, and p-terphenyl-4,4”-dithiol. The fatty amine ligands with C1 - C 30The fatty amine ligands include, but are not limited to, one or more of hexylamine, octylamine, dioctylamine, trioctylamine, nonylamine, decylamine, dodecylamine, tridecylamine, tetradecylamine, pentadecylamine, hexadecylamine, heptadecanylamine, octadecylamine and oleylamine, C6-C 30 The aromatic amine ligands include, but are not limited to, one or more of aniline, indenepropylamine, 4-octylaniline and benzidine. 30 The aliphatic phosphine ligands include, but are not limited to, one or more of trimethylphosphine, triethylphosphine, tripropylphosphine, tributylphosphine, trihexylphosphine, trioctylphosphine, tridecylphosphine, tributylphosphine oxide, trihexylphosphine oxide, trioctylphosphine oxide and tridecylphosphine oxide, C6-C 30 The aromatic phosphine ligands include, but are not limited to, one or more of bis(2-diphenylphosphinoethyl)phenylphosphine and triphenylphosphine oxide, C6~C 30 The aromatic phosphate ligands include, but are not limited to, one or more of tetraethyl p-xylene diphosphate and diphenyl ethyl phosphate. The halogen ligands include, but are not limited to, -Cl, -F, -I or -Br.

[0127] When the functional layer 103 includes a light-emitting layer 1033 and the material of the light-emitting layer 1033 includes light-emitting quantum dots, in order to improve the energy level matching between the light-emitting layer 1033 and the electronic functional layer 1031, in some embodiments of the present application, such as Figure 3 As shown, the electronic functional layer 1031 includes a first sublayer 10311 and a second sublayer 10312 which are stacked. The first sublayer 10311 and the second sublayer 10312 are described in the above thin film. The first sublayer 10311 is closer to the light-emitting layer 1033 than the second sublayer 10312. It should be noted that the amide group in the compound can form a hydrogen bond with the hydroxyl group on the surface of the metal oxide material, thereby enhancing the interface compatibility between the first sublayer 10311 and the second sublayer 10312, and reducing or eliminating the negative impact of the second sublayer 10312 on the electronic transport performance of the first sublayer 10311.

[0128] In some embodiments of the present application, the photoelectric device 10 includes a hole functional layer 1032. For the photoelectric device 10 including the hole functional layer 1032 and the electronic functional layer 1031, the hole functional layer 1032 is closer to the anode than the electronic functional layer 1031; for the photoelectric device 10 including the hole functional layer 1032, the light-emitting layer 1033 and the electronic functional layer 1031, in the direction from the anode to the cathode, the hole functional layer 1032, the light-emitting layer 1033 and the electronic functional layer 1031 are arranged in sequence.

[0129] The materials of the hole functional layer 1032 include, but are not limited to, one or more of an undoped first inorganic compound, a doped second inorganic compound, and an organic compound. Among them, the organic compounds include, but are not limited to, poly(3,4-ethylenedioxythiophene):poly(styrenesulfonic acid) (abbreviation: PEDOT:PSS, CAS No. 155090-83-8), copper phthalocyanine (CAS No. 147-14-8), titanium oxyphthalocyanine (CAS No. 26201-32-1), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinodimethane (CAS No. 29261-33-4), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (CAS No. 105598-27-4), polyaniline (CAS No. 25233-30-1), polypyrrole (CAS No. 30604-81-0), 3-hexyl-substituted polythiophene (CAS No. 104934-50-1), poly(9-vinylcarbazole) (abbreviation: PVK, CAS No. 25067-59-8), 4,4'-bis(9-carbazolyl)biphenyl (abbreviation: CBP, CAS No. 58328-31-7), poly[bis(4-phenyl)(4-butylphenyl)amine], 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline] (abbreviation: TAPC, CAS No. 58473-78-2), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine)] (abbreviation: TFB, CAS No. 220797-16-0), poly[(N,N'-(4-n-butylphenyl)-N,N'-diphenyl-1,4-phenylenediamine)-ALT-(9,9-din-octylfluorene-2,7-diyl)] (CAS No. 223569-31-1), 4,4',4'-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (CAS No. 124729-98-2), 4,4',4''-tris(carbazol-9-yl)triphenylamine (abbreviation: TCTA, CAS No. 139092-78-7), 4,4',4'-tris(2-naphthylphenylamino)triphenylamine (CAS No. 185690-41-9), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (abbreviation: NPB, CAS No. 123847-85-8), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (abbreviation: TPD, CAS No. 65181-78-4), N,N'-bis[4-(diphenylamino)phenyl]-N,N'-diphenylbenzidine (CAS No. 209980-53-0), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-9,9-spirobifluorene-2,7-diamine (abbreviation: Spiro-TPD,One or more of the following: N2,N7-di-1-naphthyl-N2,N7-diphenyl-9,9'-spirobi[9H-fluorene]-2,7-diamine (CAS No. 1033035-83-4), N2,N7-di-1-naphthyl-N2,N7-diphenyl-9,9'-spirobi[9H-fluorene]-2,7-diamine (CAS No. 932739-76-9), poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine] (abbreviation: PTTA, CAS No. 1333317-99-9), and 2,2',7,7'-tetrakis[N,N-bis(4-methoxyphenyl)amino]-9,9'-spirobifluorene (abbreviation: Spiro-omeTAD, CAS No. 207739-72-8); and / or, the non-doped first inorganic compound includes but is not limited to one or more of graphene, C60, nickel oxide (such as NiO), molybdenum oxide (such as MoO3), tungsten oxide (such as WO3), vanadium oxide (such as V2O5), p-type gallium nitride, chromium oxide (such as Cr2O3), copper oxide (such as CuO or Cu2O), copper sulfide (such as CuS), molybdenum sulfide (such as MoS2), and tungsten sulfide (such as WS2); and / or, the doped second inorganic compound is a host inorganic compound doped with a second doping element, and the host inorganic compound includes but is not limited to one or more of graphene, C60, nickel oxide (such as NiO), molybdenum oxide (such as MoO3), tungsten oxide (such as WO3), vanadium oxide (such as V2O5), p-type gallium nitride, chromium oxide (such as Cr2O3), copper oxide (such as CuO or Cu2O), copper sulfide (such as CuS), molybdenum sulfide (such as MoS2), and tungsten sulfide (such as WS2), and / or the second doping element includes but is not limited to one or more of nickel, molybdenum, tungsten, vanadium, chromium, copper, and platinum group metal elements.,

[0130] It should be noted that the hole functional layer 1032 can be a single-layer structure or a multi-layer structure, and the thickness of the hole functional layer 1032 is, for example, 10 nm to 100 nm. When the hole functional layer 1032 is a multi-layer structure, the hole functional layer 1032 includes, for example, one or more of a hole injection layer, a hole transport layer, and an electron blocking layer. For the hole functional layer 1032 including a hole injection layer, a hole transport layer, and an electron blocking layer, the hole transport layer is located between the hole injection layer and the electron blocking layer, and one of the first electrode 101 and the second electrode 102 is an anode and the other is a cathode, and the hole injection layer is closer to the anode than the electron blocking layer; for the hole functional layer 1032 including a hole transport layer and an electron blocking layer, the hole transport layer is closer to the anode than the electron blocking layer; for the hole functional layer 1032 including a hole injection layer and a hole transport layer, the hole injection layer is closer to the anode than the hole transport layer. When the hole functional layer 1032 contains multiple materials and the hole functional layer 1032 is a multi-layer structure, the multiple materials can all be in the same layer, or in different layers respectively, or part of them in the same layer. For example, as Figure 2As shown, when the hole functional layer 1032 is composed of a hole injection layer 10321 and a hole transport layer 10322 which are stacked, the material of the hole functional layer 1032 includes PEDOT:PSS and TFB, and PEDOT:PSS and TFB are in different layers respectively. The material of the hole injection layer 10321 is PEDOT:PSS, and the material of the hole transport layer 10322 is TFB.

[0131] In addition, the preparation methods of each layer in the optoelectronic device include but are not limited to chemical methods and / or physical methods. Among them, the chemical methods include but are not limited to one or more of chemical vapor deposition method, sequential ionic layer adsorption and reaction method, anodic oxidation method, electrolytic deposition method, and coprecipitation method. The physical methods include but are not limited to physical coating method and solution method. The physical coating method includes but is not limited to one or more of thermal evaporation coating method, electron beam evaporation coating method, magnetron sputtering method, multi-arc ion coating method, physical vapor deposition method, atomic layer deposition method, and pulsed laser deposition method. The solution method includes but is not limited to one or more of spin coating method, printing method, inkjet printing method, blade coating method, printing method, dip coating method, immersion method, spraying method, roll coating method, casting method, slot die coating method, and bar coating method.

[0132] The embodiment of the present application also provides an electronic device, and the electronic device includes any one of the optoelectronic devices described in the embodiment of the present application. The electronic device can be, for example, any electronic product with a display function, including but not limited to smartphone, tablet personal computer, mobile phone, video telephone, e-book reader, laptop PC, netbook computer, workstation, server, personal digital assistant, portable multimedia player, MP3 player, mobile medical device, camera, game console, digital camera, in-vehicle navigator, electronic billboard, automated teller machine, smart bracelet, smart watch, Virtual Reality (VR) device, or wearable device.

[0133] Hereinafter, the technical solutions and technical effects of the present application will be described in detail through specific examples, comparative examples, and experimental examples. The following examples are only partial examples of the present application and do not specifically limit the present application.

[0134] Compound Example 1

[0135] This embodiment provides a compound and a preparation method thereof. The compound has the structure shown in the following formula (1.1):

[0136]

[0137] The preparation method of the compound comprises the following steps:

[0138] S1.1. Under a nitrogen atmosphere and at 20 °C, 500 mg of L-phenylalanine, 297 mg of HOBt, 421 mg of EDCl, and 50 mL of dichloromethane (abbreviated as DCM, CAS No. 75-09-2) are mixed and stirred in a 100 mL round-bottom flask for 0.5 h. Then, 447 mg of 2,3-diamino-3-oxopropanoic acid (CAS No. 57471-67-7) is added thereto to obtain a first reaction system. The first reaction system is subjected to a first amide coupling reaction under a nitrogen atmosphere and at 20 °C for 12 h to obtain a first reaction product. The first reaction product is subjected to vacuum distillation to remove dichloromethane, and the solid obtained after vacuum distillation is dissolved in ethyl acetate. Then, it is successively extracted with a 3.6% hydrochloric acid aqueous solution, a 5% sodium carbonate aqueous solution, and a 5% sodium chloride solution. The organic phase is collected, and then the organic phase is successively subjected to anhydrous sodium sulfate drying and vacuum distillation to obtain Intermediate 1;

[0139] S1.2. 265 mg of Intermediate 1 (prepared in step S1.1), 31.4 mg of bromobenzene, 20 mL of dichloromethane, and 50 mg of an acid-binding agent (sodium bicarbonate) are placed in a 100 mL round-bottom flask and mixed to obtain a second reaction system. Then, the second reaction system is subjected to a substitution reaction under a nitrogen atmosphere and at 60 °C for 12 h to obtain a second reaction product. The second reaction product is subjected to vacuum distillation to remove dichloromethane, and the solid obtained after vacuum distillation is dissolved in ethyl acetate. Then, it is successively extracted with a 3.6% hydrochloric acid aqueous solution, a 5% sodium carbonate aqueous solution, and a 5% sodium chloride solution. The organic phase is collected, and then the organic phase is successively subjected to anhydrous sodium sulfate drying and vacuum distillation to obtain Intermediate 2;

[0140] S1.3. Under a nitrogen atmosphere and at 20 °C, 1.26 g of intermediate 2 (prepared in step S1.2), 297 mg of HOBt, 421 mg of EDCl, and 50 mL of DCM were mixed and stirred in a 100 mL round-bottom flask for 0.5 h. Then, 688 mg of n-pentadecylamine was added thereto to obtain a third reaction system. The third reaction system was subjected to a second amide coupling reaction under a nitrogen atmosphere and at 20 °C for 12 h to obtain a third reaction product. The third reaction product was subjected to vacuum distillation to remove dichloromethane, and the solid obtained after vacuum distillation was dissolved in ethyl acetate. Then, it was successively extracted with an aqueous hydrochloric acid solution with a mass percentage of 3.6%, an aqueous sodium carbonate solution with a mass percentage of 5%, and an aqueous sodium chloride solution with a mass percentage of 5%. The organic phase was collected, and then the organic phase was successively subjected to the processes of drying with anhydrous sodium sulfate and vacuum distillation to obtain a solid, and the solid is the compound shown in formula (1.1).

[0141] Among them, the solid prepared in step S1.3 was subjected to NMR characterization, and the NMR spectrum is as Figure 4 shown, proving that the solid prepared in step S1.3 is the compound shown in formula (1.1).

[0142] Compound Example 2

[0143] This example provides a compound and a preparation method thereof. The compound has the structure shown in the following formula (1.2):

[0144]

[0145] Compared with the preparation method of the compound shown in formula (1.1) in Compound Example 1, the difference in the preparation method of the compound with the structure shown in formula (1.2) in this example is that: "688 mg of n-pentadecylamine" in step S1.3 is replaced with "387.72 mg of n-octylamine".

[0146] The product prepared in this example was subjected to NMR characterization, and the NMR spectrum is as Figure 5 shown, proving that the product prepared in this example is the compound shown in formula (1.2).

[0147] Compound Example 3

[0148] This example provides a compound and a preparation method thereof. The compound has the structure shown in the following formula (1.3):

[0149]

[0150] Compared with the preparation method of the compound shown in formula (1.1) in Compound Example 1, the difference in the preparation method of the compound with the structure shown in formula (1.3) in this example is that: "688 mg of n-pentadecylamine" in step S1.3 is replaced with "802.5 mg of oleylamine".

[0151] The product obtained in this example was characterized by NMR, and the NMR spectrum is as Figure 6 shown, proving that the product obtained in this example is the compound shown in formula (1.3).

[0152] Compound 4

[0153] This example provides a compound and its preparation method, and the compound has the structure shown in the following formula (1.4):

[0154]

[0155] Compared with the preparation method of the compound shown in formula (1.1) in Compound Example 1, the difference in the preparation method of the compound with the structure shown in formula (1.4) in this example is that: "688 mg of n-pentadecylamine" in step S1.3 is replaced with "604.1 mg of O-dodecylhydroxylamine (CAS No. 40345-87-7)".

[0156] The product obtained in this example was characterized by NMR, and the NMR spectrum is as Figure 7 shown, proving that the product obtained in this example is the compound shown in formula (1.4).

[0157] Compound 5

[0158] This example provides a compound and its preparation method, and the compound has the structure shown in the following formula (1.5):

[0159]

[0160] Compared with the preparation method of the compound shown in formula (1.1) in Compound Example 1, the difference in the preparation method of the compound with the structure shown in formula (1.5) in this example is that: "688 mg of n-pentadecylamine" in step S1.3 is replaced with "640.2 mg of the compound with CAS No. 168706-09-0".

[0161] The product obtained in this example was characterized by NMR, and the NMR spectrum is as Figure 8 shown, proving that the product obtained in this example is the compound shown in formula (1.5).

[0162] Compound 6

[0163] This embodiment provides a compound and a preparation method thereof. The compound has the structure shown in the following formula (1.6):

[0164]

[0165] Compared with the preparation method of the compound shown in formula (1.1) in Compound Example 1, the difference in the preparation method of the compound with the structure shown in formula (1.6) in this embodiment is that: "688 mg of n-pentadecylamine" in step S1.3 is replaced with "1061 mg of n-tetracosylamine (CAS No.: 14130-08-6)".

[0166] The product obtained in this embodiment was characterized by nuclear magnetic resonance, and the nuclear magnetic resonance spectrum is as Figure 9 shown, proving that the product obtained in this embodiment is the compound shown in formula (1.6).

[0167] Compound 7

[0168] This embodiment provides a compound and a preparation method thereof. The compound has the structure shown in the following formula (1.7):

[0169]

[0170] Compared with the preparation method of the compound shown in formula (1.1) in Compound Example 1, the difference in the preparation method of the compound with the structure shown in formula (1.7) in this embodiment is that: "688 mg of n-pentadecylamine" in step S1.3 is replaced with "279.38 mg of aniline (CAS No.: 62-53-3)".

[0171] The product obtained in this embodiment was characterized by nuclear magnetic resonance, and the nuclear magnetic resonance spectrum is as Figure 10 shown, proving that the product obtained in this embodiment is the compound shown in formula (1.7).

[0172] Film Example 1

[0173] This embodiment provides a film and a preparation method thereof. The film is a single-layer structure, and the materials of the film include nano-ZnO (average particle size: 5 nm) and the compound with the structure shown in formula (1.1). The mass ratio of the compound with the structure shown in formula (1.1) in the total mass of the film is 0.5%.

[0174] The preparation method of the film includes the following steps:

[0175] S2.1: Provide a 10 mL nano-ZnO-ethanol solution with a concentration of 30 mg / mL, and disperse 1.5 mg of the compound with the structure shown in formula (1.1) in the nano-ZnO-ethanol solution to obtain a composite material solution;

[0176] S2.2. Provide a glass substrate, spin-coat the composite material solution prepared in step S1.1 on one side of the glass substrate, and then place it in a constant temperature heat treatment at 80 °C to cure into a film, obtaining a film with a thickness of 45 nm.

[0177] Film Example 2

[0178] This example provides a film and a preparation method thereof. The film has a single-layer structure, and the materials of the film include nano-ZnO (average particle size of 5 nm) and a compound with the structure shown in formula (1.1). The mass ratio of the compound with the structure shown in formula (1.1) to the total mass of the film is 1%.

[0179] Compared with the film preparation method in Film Example 1, the difference in the film preparation method in this example is that in step S2.1, "dispersing 1.5 mg of the compound with the structure shown in formula (1.1) in the nano-ZnO-ethanol solution" is replaced by "dispersing 3.0 mg of the compound with the structure shown in formula (1.1) in the nano-ZnO-ethanol solution".

[0180] Film Example 3

[0181] This example provides a film and a preparation method thereof. The film has a single-layer structure, and the materials of the film include nano-ZnO (average particle size of 5 nm) and a compound with the structure shown in formula (1.1). The mass ratio of the compound with the structure shown in formula (1.1) to the total mass of the film is 1.5%.

[0182] Compared with the film preparation method in Film Example 1, the difference in the film preparation method in this example is that in step S2.1, "dispersing 1.5 mg of the compound with the structure shown in formula (1.1) in the nano-ZnO-ethanol solution" is replaced by "dispersing 4.57 mg of the compound with the structure shown in formula (1.1) in the nano-ZnO-ethanol solution".

[0183] Film Example 4

[0184] This example provides a film and a preparation method thereof. The film has a single-layer structure, and the materials of the film include nano-ZnO (average particle size of 5 nm) and a compound with the structure shown in formula (1.1). The mass ratio of the compound with the structure shown in formula (1.1) to the total mass of the film is 3%.

[0185] Compared with the film preparation method in Film Example 1, the difference in the film preparation method in this example is that in step S2.1, "dispersing 1.5 mg of the compound with the structure shown in formula (1.1) in the nano-ZnO-ethanol solution" is replaced by "dispersing 9.14 mg of the compound with the structure shown in formula (1.1) in the nano-ZnO-ethanol solution".

[0186] Thin Film Example 5

[0187] This example provides a thin film and a preparation method thereof. The thin film is a single-layer structure, and the material of the thin film includes nano-Zn 0.85 Mg 0.15 O (average particle size is 5 nm) and a compound having the structure shown in formula (1.1). The proportion of the compound having the structure shown in formula (1.1) in the total mass of the thin film is 1%.

[0188] Compared with the preparation method of the thin film in Thin Film Example 1, the difference in the preparation method of the thin film in this example is that: in step S2.1, “dispersing 1.5 mg of the compound having the structure shown in formula (1.1) in the nano-ZnO-ethanol solution” is replaced with “dispersing 3.0 mg of the compound having the structure shown in formula (1.1) in the nano-Zn 0.85 Mg 0.15 O-ethanol solution”.

[0189] Thin Film Example 6

[0190] This example provides a thin film and a preparation method thereof. The thin film is a single-layer structure, and the material of the thin film includes nano-ZnO (average particle size is 5 nm) and a compound having the structure shown in formula (1.2). The proportion of the compound having the structure shown in formula (1.1) in the total mass of the thin film is 1%.

[0191] Compared with the preparation method of the thin film in Thin Film Example 1, the difference in the preparation method of the thin film in this example is that: in step S2.1, “dispersing 1.5 mg of the compound having the structure shown in formula (1.2) in the nano-ZnO-ethanol solution” is replaced with “dispersing 3.0 mg of the compound having the structure shown in formula (1.1) in the nano-ZnO-ethanol solution”.

[0192] Thin Film Example 7

[0193] This example provides a thin film and a preparation method thereof. The thin film is a single-layer structure, and the material of the thin film includes nano-ZnO (average particle size is 5 nm) and a compound having the structure shown in formula (1.3). The proportion of the compound having the structure shown in formula (1.1) in the total mass of the thin film is 1%.

[0194] Compared with the preparation method of the thin film in Thin Film Example 1, the difference in the preparation method of the thin film in this example is that: in step S2.1, “dispersing 1.5 mg of the compound having the structure shown in formula (1.3) in the nano-ZnO-ethanol solution” is replaced with “dispersing 3.0 mg of the compound having the structure shown in formula (1.1) in the nano-ZnO-ethanol solution”.

[0195] Film Example 8

[0196] This example provides a film and a preparation method thereof. The film is a single-layer structure, and the materials of the film include nano-ZnO (average particle size of 5 nm) and a compound with the structure shown in formula (1.7). The mass ratio of the compound with the structure shown in formula (1.1) to the total mass of the film is 1%.

[0197] Compared with the film preparation method in Film Example 1, the difference in the film preparation method in this example is that in step S2.1, "dispersing 1.5 mg of the compound with the structure shown in formula (1.7) in the nano-ZnO-ethanol solution" is replaced by "dispersing 3.0 mg of the compound with the structure shown in formula (1.1) in the nano-ZnO-ethanol solution".

[0198] Film Example 9

[0199] This example provides a film and a preparation method thereof. The film is a double-layer structure, and the film consists of a first sub-layer and a second sub-layer stacked in sequence. The material of the first sub-layer is nano-ZnO (average particle size of 5 nm), the thickness of the first sub-layer is 35 nm, the material of the second sub-layer is a compound with the structure shown in formula (1.1), and the thickness of the second sub-layer is 10 nm.

[0200] The preparation method of the film includes the following steps:

[0201] S3.1: Provide a glass substrate, spin-coat a nano-ZnO-ethanol solution with a concentration of 30 mg / mL on one side of the glass substrate, and then place it in a constant temperature heat treatment at 80 °C to cure into a film to obtain the first sub-layer;

[0202] S3.2: Spin-coat a solution of the compound with the structure shown in formula (1.1) - n-octane with a concentration of 3.5 mg / mL on the side of the first sub-layer away from the glass substrate, and then place it in a constant temperature heat treatment at 80 °C to cure into a film to obtain the second sub-layer.

[0203] Film Example 10

[0204] This example provides a film and a preparation method thereof. The film is a double-layer structure, and the film consists of a first sub-layer and a second sub-layer stacked in sequence. The material of the first sub-layer is nano-ZnO (average particle size of 5 nm), the thickness of the first sub-layer is 35 nm, the material of the second sub-layer is a compound with the structure shown in formula (1.2), and the thickness of the second sub-layer is 10 nm.

[0205] The preparation method of the film in this example is carried out with reference to the film preparation method in Film Example 9.

[0206] Film Example 11

[0207] This embodiment provides a thin film and a preparation method thereof. The thin film has a bilayer structure and is composed of a first sub-layer and a second sub-layer which are stacked in sequence. The material of the first sub-layer is nano-ZnO (average particle size is 5 nm), the thickness of the first sub-layer is 35 nm, the material of the second sub-layer is a compound with the structure shown in formula (1.3), and the thickness of the second sub-layer is 10 nm.

[0208] The preparation method of the thin film in this embodiment is carried out with reference to the preparation method of the thin film in Thin Film Embodiment 9.

[0209] Thin Film Embodiment 12

[0210] This embodiment provides a thin film and a preparation method thereof. The thin film has a bilayer structure and is composed of a first sub-layer and a second sub-layer which are stacked in sequence. The material of the first sub-layer is nano-ZnO (average particle size is 5 nm), the thickness of the first sub-layer is 35 nm, the material of the second sub-layer is a compound with the structure shown in formula (1.4), and the thickness of the second sub-layer is 10 nm.

[0211] The preparation method of the thin film in this embodiment is carried out with reference to the preparation method of the thin film in Thin Film Embodiment 9.

[0212] Thin Film Embodiment 13

[0213] This embodiment provides a thin film and a preparation method thereof. The thin film has a bilayer structure and is composed of a first sub-layer and a second sub-layer which are stacked in sequence. The material of the first sub-layer is nano-ZnO (average particle size is 5 nm), the thickness of the first sub-layer is 35 nm, the material of the second sub-layer is a compound with the structure shown in formula (1.5), and the thickness of the second sub-layer is 10 nm.

[0214] The preparation method of the thin film in this embodiment is carried out with reference to the preparation method of the thin film in Thin Film Embodiment 9.

[0215] Thin Film Embodiment 14

[0216] This embodiment provides a thin film and a preparation method thereof. The thin film has a bilayer structure and is composed of a first sub-layer and a second sub-layer which are stacked in sequence. The material of the first sub-layer is nano-ZnO (average particle size is 5 nm), the thickness of the first sub-layer is 35 nm, the material of the second sub-layer is a compound with the structure shown in formula (1.6), and the thickness of the second sub-layer is 10 nm.

[0217] The preparation method of the thin film in this embodiment is carried out with reference to the preparation method of the thin film in Thin Film Embodiment 9.

[0218] Thin Film Embodiment 15

[0219] This embodiment provides a thin film and a preparation method thereof. The thin film has a bilayer structure and is composed of a first sub-layer and a second sub-layer which are stacked in sequence. The material of the first sub-layer is nano-ZnO (average particle size is 5 nm), the thickness of the first sub-layer is 35 nm, the material of the second sub-layer is a compound with the structure shown in formula (1.7), and the thickness of the second sub-layer is 10 nm.

[0220] In this embodiment, the preparation method of the thin film is carried out with reference to the preparation method of the thin film in Thin Film Embodiment 9.

[0221] Thin Film Embodiment 16

[0222] This embodiment provides a thin film and a preparation method thereof. The thin film has a bilayer structure and is composed of a first sub-layer and a second sub-layer which are stacked in sequence. The material of the first sub-layer is nano-ZnO (average particle size is 5 nm), the thickness of the first sub-layer is 30 nm, the material of the second sub-layer is a compound with the structure shown in formula (1.1), and the thickness of the second sub-layer is 15 nm.

[0223] In this embodiment, the preparation method of the thin film is carried out with reference to the preparation method of the thin film in Thin Film Embodiment 9.

[0224] Thin Film Comparative Example

[0225] This comparative example provides a thin film and a preparation method thereof. The thin film has a single-layer structure, the material of the thin film is nano-ZnO (average particle size is 5 nm), and the thickness of the thin film is 45 nm.

[0226] The preparation method of the thin film in this comparative example includes the steps of: providing a glass substrate, spin-coating a nano-ZnO-ethanol solution with a concentration of 30 mg / mL on one side of the glass substrate, and then placing it in a constant temperature heat treatment at 80 °C to cure into a film to obtain the thin film.

[0227] Device Embodiment 1

[0228] This embodiment provides an optoelectronic device and a preparation method thereof. The optoelectronic device is a quantum dot light-emitting diode with a normal structure, such as Figure 2As shown, the optoelectronic device 10 includes a first electrode 101, a functional layer 103, and a second electrode 102 that are sequentially stacked. The first electrode 101 is an anode and the second electrode 102 is a cathode. In the upward direction, the functional layer 103 includes a hole functional layer 1032, a light-emitting layer 1033, and an electron functional layer 1031 that are sequentially stacked. The hole functional layer 1032 is closer to the first electrode 101 than the electron functional layer 1031; the hole functional layer 1032 is composed of a hole injection layer 10321 and a hole transport layer 10322 that are stacked, and the hole injection layer 10321 is closer to the first electrode 101 than the hole transport layer 10322; the electron functional layer 1031 is a single-layer structure. The light-emitting area of the optoelectronic device 10 is 0.04 cm 2 .

[0229] The materials and thicknesses of each layer in the optoelectronic device 10 are as follows:

[0230] The material of the first electrode 101 is ITO, and the average thickness of the first electrode 101 is 30 nm;

[0231] The material of the second electrode 102 is Ag, and the average thickness of the second electrode 102 is 100 nm;

[0232] The material of the light-emitting layer 1033 is CdSe / ZnS quantum dots, the emission color is green, and the average thickness of the light-emitting layer 1033 is 20 nm;

[0233] The electron functional layer 1031 is the thin film prepared in Thin Film Example 1;

[0234] The material of the hole injection layer 10321 is PEDOT:PSS, and the thickness of the hole injection layer 10321 is 30 nm;

[0235] The material of the hole transport layer 10322 is TFB, and the thickness of the hole transport layer 10322 is 20 nm.

[0236] The preparation method of the optoelectronic device in this embodiment includes the following steps:

[0237] S10.1. Provide a substrate, sputter ITO on one side of the substrate to obtain an ITO layer, wipe the surface of the ITO layer with a cotton swab dipped in a small amount of soapy water to remove visible impurities on the surface, and then sequentially ultrasonically clean the substrate including ITO in deionized water for 15 min, in acetone for 15 min, in ethanol for 15 min, and in isopropanol for 15 min. After drying, perform ultraviolet-ozone surface treatment for 20 min to obtain a substrate including the first electrode;

[0238] S10.2. Under the air environment of normal temperature and pressure, spin-coat an aqueous solution of PEDOT:PSS with a mass fraction of 2.8% on the side of the first electrode far from the substrate, and then place it in a constant-temperature heat treatment at 150 °C to solidify into a film to obtain a hole injection layer;

[0239] S10.3. Under the nitrogen environment of normal temperature and pressure, spin-coat a TFB-chlorobenzene solution with a concentration of 8 mg / mL on the side of the hole injection layer far from the first electrode, and then place it in a constant-temperature heat treatment at 170 °C under a nitrogen atmosphere to solidify into a film to obtain a hole transport layer;

[0240] S10.4. Under the nitrogen environment of normal temperature and pressure, spin-coat a CdSe / ZnS quantum dot - n-octane solution with a concentration of 25 mg / mL on the side of the hole transport layer far from the hole injection layer, and then place it in a constant-temperature heat treatment at 80 °C under a nitrogen atmosphere to solidify into a film to obtain a light-emitting layer;

[0241] S10.5. Under the nitrogen environment of normal temperature and pressure, form an electron functional layer on the side of the light-emitting layer far from the hole transport layer with reference to the film preparation method in Film Example 1;

[0242] S10.6. Place the stacked structure completed in step S10.5 into an evaporation chamber with a vacuum degree not higher than 3×10 -4 Pa, thermally evaporate Ag on the side of the electron functional layer far from the light-emitting layer by using a thermal evaporation process to obtain a second electrode, and then encapsulate it with a non-acid epoxy resin LOCTITE 3335 to obtain an optoelectronic device.

[0243] Device Example 2

[0244] This example provides an optoelectronic device and its preparation method. Compared with the optoelectronic device in Device Example 1, the difference of the optoelectronic device in this example is that the electron functional layer is replaced with the film prepared in Film Example 2.

[0245] Compared with the preparation method of the optoelectronic device in Device Example 1, the difference of the preparation method of the optoelectronic device in this example is that step S10.5 is replaced with "Under the nitrogen environment of normal temperature and pressure, form an electron functional layer on the side of the light-emitting layer far from the hole transport layer with reference to the film preparation method in Film Example 2".

[0246] Device Example 3

[0247] This example provides an optoelectronic device and its preparation method. Compared with the optoelectronic device in Device Example 1, the difference of the optoelectronic device in this example is that the electron functional layer is replaced with the film prepared in Film Example 3.

[0248] Compared with the preparation method of the optoelectronic device in Device Example 1, the difference in the preparation method of the optoelectronic device in this example is that step S10.5 is replaced with "Under normal temperature and pressure in a nitrogen environment, an electron functional layer is formed on the side of the light-emitting layer away from the hole transport layer with reference to the preparation method of the thin film in Thin Film Example 3."

[0249] Device Example 4

[0250] This example provides an optoelectronic device and its preparation method. Compared with the optoelectronic device in Device Example 1, the difference in the optoelectronic device in this example is that the electron functional layer is replaced with the thin film obtained in Thin Film Example 4.

[0251] Compared with the preparation method of the optoelectronic device in Device Example 1, the difference in the preparation method of the optoelectronic device in this example is that step S10.5 is replaced with "Under normal temperature and pressure in a nitrogen environment, an electron functional layer is formed on the side of the light-emitting layer away from the hole transport layer with reference to the preparation method of the thin film in Thin Film Example 4."

[0252] Device Example 5

[0253] This example provides an optoelectronic device and its preparation method. Compared with the optoelectronic device in Device Example 1, the difference in the optoelectronic device in this example is that the electron functional layer is replaced with the thin film obtained in Thin Film Example 5.

[0254] Compared with the preparation method of the optoelectronic device in Device Example 1, the difference in the preparation method of the optoelectronic device in this example is that step S10.5 is replaced with "Under normal temperature and pressure in a nitrogen environment, an electron functional layer is formed on the side of the light-emitting layer away from the hole transport layer with reference to the preparation method of the thin film in Thin Film Example 5."

[0255] Device Example 6

[0256] This example provides an optoelectronic device and its preparation method. Compared with the optoelectronic device in Device Example 1, the difference in the optoelectronic device in this example is that the electron functional layer is replaced with the thin film obtained in Thin Film Example 6.

[0257] Compared with the preparation method of the optoelectronic device in Device Example 1, the difference in the preparation method of the optoelectronic device in this example is that step S10.5 is replaced with "Under normal temperature and pressure in a nitrogen environment, an electron functional layer is formed on the side of the light-emitting layer away from the hole transport layer with reference to the preparation method of the thin film in Thin Film Example 6."

[0258] Device Example 7

[0259] This embodiment provides an optoelectronic device and a method for manufacturing the same. Compared with the optoelectronic device in Device Embodiment 1, the difference of the optoelectronic device in this embodiment is that the electronic functional layer is replaced with the thin film obtained in Thin Film Embodiment 7.

[0260] Compared with the method for manufacturing the optoelectronic device in Device Embodiment 1, the difference of the method for manufacturing the optoelectronic device in this embodiment is that step S10.5 is replaced with "forming an electronic functional layer on the side of the light-emitting layer away from the hole transport layer under a nitrogen environment at normal temperature and pressure with reference to the method for manufacturing the thin film in Thin Film Embodiment 7".

[0261] Device Embodiment 8

[0262] This embodiment provides an optoelectronic device and a method for manufacturing the same. Compared with the optoelectronic device in Device Embodiment 1, the difference of the optoelectronic device in this embodiment is that the electronic functional layer is replaced with the thin film obtained in Thin Film Embodiment 8.

[0263] Compared with the method for manufacturing the optoelectronic device in Device Embodiment 1, the difference of the method for manufacturing the optoelectronic device in this embodiment is that step S10.5 is replaced with "forming an electronic functional layer on the side of the light-emitting layer away from the hole transport layer under a nitrogen environment at normal temperature and pressure with reference to the method for manufacturing the thin film in Thin Film Embodiment 8".

[0264] Device Embodiment 9

[0265] This embodiment provides an optoelectronic device and a method for manufacturing the same. Compared with the optoelectronic device in Device Embodiment 1, the difference of the optoelectronic device in this embodiment is that the electronic functional layer is replaced with the thin film obtained in Thin Film Embodiment 9, that is, the optoelectronic device has a structure as Figure 3 shown.

[0266] Compared with the method for manufacturing the optoelectronic device in Device Embodiment 1, the difference of the method for manufacturing the optoelectronic device in this embodiment is that step S10.5 is replaced with "forming an electronic functional layer on the side of the light-emitting layer away from the hole transport layer under a nitrogen environment at normal temperature and pressure with reference to the method for manufacturing the thin film in Thin Film Embodiment 9".

[0267] Device Embodiment 10

[0268] This embodiment provides an optoelectronic device and a method for manufacturing the same. Compared with the optoelectronic device in Device Embodiment 1, the difference of the optoelectronic device in this embodiment is that the electronic functional layer is replaced with the thin film obtained in Thin Film Embodiment 10, that is, the optoelectronic device has a structure as Figure 3 shown.

[0269] Compared with the preparation method of the optoelectronic device in Device Example 1, the difference in the preparation method of the optoelectronic device in this example is that step S10.5 is replaced with "in a nitrogen environment at normal temperature and pressure, form an electron functional layer on the side of the light-emitting layer away from the hole transport layer with reference to the preparation method of the thin film in Thin Film Example 10".

[0270] Device Example 11

[0271] This example provides an optoelectronic device and its preparation method. Compared with the optoelectronic device in Device Example 1, the difference in the optoelectronic device in this example is that the electron functional layer is replaced with the thin film prepared in Thin Film Example 11, that is, the optoelectronic device has a structure as Figure 3 shown.

[0272] Compared with the preparation method of the optoelectronic device in Device Example 1, the difference in the preparation method of the optoelectronic device in this example is that step S10.5 is replaced with "in a nitrogen environment at normal temperature and pressure, form an electron functional layer on the side of the light-emitting layer away from the hole transport layer with reference to the preparation method of the thin film in Thin Film Example 11".

[0273] Device Example 12

[0274] This example provides an optoelectronic device and its preparation method. Compared with the optoelectronic device in Device Example 1, the difference in the optoelectronic device in this example is that the electron functional layer is replaced with the thin film prepared in Thin Film Example 12, that is, the optoelectronic device has a structure as Figure 3 shown.

[0275] Compared with the preparation method of the optoelectronic device in Device Example 1, the difference in the preparation method of the optoelectronic device in this example is that step S10.5 is replaced with "in a nitrogen environment at normal temperature and pressure, form an electron functional layer on the side of the light-emitting layer away from the hole transport layer with reference to the preparation method of the thin film in Thin Film Example 12".

[0276] Device Example 13

[0277] This example provides an optoelectronic device and its preparation method. Compared with the optoelectronic device in Device Example 1, the difference in the optoelectronic device in this example is that the electron functional layer is replaced with the thin film prepared in Thin Film Example 13, that is, the optoelectronic device has a structure as Figure 3 shown.

[0278] Compared with the preparation method of the optoelectronic device in Device Example 1, the difference in the preparation method of the optoelectronic device in this example is that step S10.5 is replaced with "in a nitrogen environment at normal temperature and pressure, form an electron functional layer on the side of the light-emitting layer away from the hole transport layer with reference to the preparation method of the thin film in Thin Film Example 13".

[0279] Device Embodiment 14

[0280] This embodiment provides an optoelectronic device and a method for preparing the same. Compared with the optoelectronic device in Device Embodiment 1, the difference of the optoelectronic device in this embodiment is that: the electronic functional layer is replaced with the thin film prepared in Thin Film Embodiment 14, that is, the optoelectronic device has a structure as shown in Figure 3 shown.

[0281] Compared with the method for preparing the optoelectronic device in Device Embodiment 1, the difference of the method for preparing the optoelectronic device in this embodiment is that: step S10.5 is replaced with "forming an electronic functional layer on the side of the light-emitting layer away from the hole transport layer under normal temperature and pressure in a nitrogen environment with reference to the method for preparing the thin film in Thin Film Embodiment 14".

[0282] Device Embodiment 15

[0283] This embodiment provides an optoelectronic device and a method for preparing the same. Compared with the optoelectronic device in Device Embodiment 1, the difference of the optoelectronic device in this embodiment is that: the electronic functional layer is replaced with the thin film prepared in Thin Film Embodiment 15, that is, the optoelectronic device has a structure as shown in Figure 3 shown.

[0284] Compared with the method for preparing the optoelectronic device in Device Embodiment 1, the difference of the method for preparing the optoelectronic device in this embodiment is that: step S10.5 is replaced with "forming an electronic functional layer on the side of the light-emitting layer away from the hole transport layer under normal temperature and pressure in a nitrogen environment with reference to the method for preparing the thin film in Thin Film Embodiment 15".

[0285] Device Embodiment 16

[0286] This embodiment provides an optoelectronic device and a method for preparing the same. Compared with the optoelectronic device in Device Embodiment 1, the difference of the optoelectronic device in this embodiment is that: the electronic functional layer is replaced with the thin film prepared in Thin Film Embodiment 16, that is, the optoelectronic device has a structure as shown in Figure 3 shown.

[0287] Compared with the method for preparing the optoelectronic device in Device Embodiment 1, the difference of the method for preparing the optoelectronic device in this embodiment is that: step S10.5 is replaced with "forming an electronic functional layer on the side of the light-emitting layer away from the hole transport layer under normal temperature and pressure in a nitrogen environment with reference to the method for preparing the thin film in Thin Film Embodiment 16".

[0288] Device Comparative Example

[0289] This comparative example provides an optoelectronic device and a method for preparing the same. Compared with the optoelectronic device in Device Embodiment 1, the difference of the optoelectronic device in this embodiment is that: the electronic functional layer is replaced with the thin film prepared in Thin Film Comparative Example 1.

[0290] Compared with the method for preparing the optoelectronic device in Device Example 1, the difference in the method for preparing the optoelectronic device in this example is that step S10.5 is replaced with "Under normal temperature and pressure in a nitrogen environment, an electron functional layer is formed on the side of the light-emitting layer away from the hole transport layer with reference to the method for preparing the thin film in Thin Film Comparative Example 1".

[0291] Experimental Example 1

[0292] Atomic force microscopy was used to detect the surface roughness Ra1 (nm) of the thin films prepared in Thin Film Examples 1 to 16 and the thin film in the thin film comparative example in the first state and the surface roughness Ra2 (nm) in the second state. Among them, the first state is the state after being placed for 1 h in an environment with a temperature of 30 °C and a relative humidity of 50%, and the second state is the state after being placed for 7 days in an environment with a temperature of 30 °C and a relative humidity of 80%. The test results are shown in Table 1 below:

[0293] Table 1

[0294]

[0295]

[0296] As can be seen from Table 1, compared with Ra1 of the thin film prepared in the thin film comparative example, Ra1 of the thin films prepared in Thin Film Examples 1 to 16 is lower, and compared with Ra2 of the thin film prepared in the thin film comparative example, Ra2 of the thin films prepared in Thin Film Examples 1 to 16 is lower; in addition, compared with the difference between Ra2 and Ra1 of the thin film prepared in the thin film comparative example, the difference between Ra2 and Ra1 of the thin films prepared in Thin Film Examples 1 to 16 is significantly smaller.

[0297] It can be seen from this that compared with the thin film made of a metal oxide material, the thin film made of a metal oxide material and the compound has higher hydrophobicity, effectively improves the problem of "agglomeration" of the metal oxide material due to water and oxygen erosion, and reduces the surface roughness of the thin film.

[0298] Experimental Example 2

[0299] The performance of the optoelectronic devices in Device Examples 1 to 16 and the device comparative example in the state of being encapsulated for 1 h was respectively detected. The performance test was carried out in an environment with a temperature of 25 °C and a relative humidity of 40%.

[0300] The optoelectronic performance was detected using a FushiDa FPD optical property measurement device (including an Ocean Optics USB2000, a LabView-controlled QE-PRO spectrometer, a Keithley 2400, a high-precision digital source meter Keithley 6485, an optical fiber with an inner diameter of 50 μm, device test probes and fixtures, various related connecting wires and data cards, an efficiency test dark box, and a data acquisition system, etc., to build an efficiency test system), obtaining parameters such as the turn-on voltage, current, brightness, and emission spectrum of each optoelectronic device, and then calculating key parameters such as the external quantum efficiency and power efficiency.

[0301] Among them, the detection method of current efficiency includes the steps: setting the luminous area to 2 mm × 2 mm = 4 mm 2 , discontinuously collecting the brightness values of the optoelectronic device in the voltage range of 0 V to 8 V, collecting once every 0.2 V, and dividing the brightness value collected each time by the corresponding current density to obtain the current efficiency of the optoelectronic device under the collection conditions of that time, and obtaining the current efficiency (C.E0, cd / A) at a current density of 32 mA / cm 2 .

[0302] The detection method of device lifetime includes the steps: under the drive of a constant current (2 mA), using a lifetime test device to perform electroluminescence lifetime analysis on each optoelectronic device, and recording the time (T95, h) required for each optoelectronic device to decay from the maximum brightness to 95%.

[0303] The detection method of device efficiency stability includes the steps: after placing the packaged optoelectronic device in an environment with a temperature of 30 °C and a relative humidity of 80% for 7 days, discontinuously collecting the brightness values of the optoelectronic device in the voltage range of 0 V to 8 V, collecting once every 0.2 V, and dividing the brightness value collected each time by the corresponding current density to obtain the current efficiency of the optoelectronic device under the collection conditions of that time, and obtaining the current efficiency (C.E1, cd / A) at a current density of 32 mA / cm 2 , calculating to obtain A(%) = 100% – E1 / C.E0 × 100%, the larger the A%, the higher the stability of the device efficiency of the optoelectronic device, and vice versa, the smaller the A%, the lower the stability of the device efficiency of the optoelectronic device.

[0304] The performance detection results of each optoelectronic device are shown in Table 2 below:

[0305] Table 2

[0306]

[0307]

[0308] As can be seen from Table 2, compared with the optoelectronic devices in the device comparative examples, the optoelectronic devices in Device Examples 1 to Device Example 16 have significant advantages in comprehensive performance, specifically manifested as follows: the optoelectronic devices in Device Examples 1 to Device Example 16 have higher device efficiency, longer device life, and better performance stability. Taking the optoelectronic device in Device Example 5 as an example, the C.E0 of the optoelectronic device in Device Example 5 is 1.7 times that of the optoelectronic device in the device comparative example, the T95 of the optoelectronic device in Device Example 5 is 1.4 times that of the optoelectronic device in the device comparative example, and the A% of the optoelectronic device in Device Example 5 is 24.7% higher than that of the optoelectronic device in the device comparative example.

[0309] It can be seen from this that the material of the functional layer in the optoelectronic device includes the compound represented by the general formula (I-1), which can reduce or eliminate the negative impact on the performance of the optoelectronic device caused by external water and oxygen erosion, improve the device efficiency and device life of the optoelectronic device, and is beneficial to improving the performance stability of the optoelectronic device. Further, when the material of the electron functional layer in the optoelectronic device includes the compound represented by the general formula (I-1) and a metal oxide material, the compound can modify the metal oxide material, inhibit the shedding and migration of metal ions, and effectively improve the problem of "agglomeration" of the metal oxide material due to water and oxygen erosion. In addition, the amide group in the compound can form a hydrogen bond with the hydroxyl group on the surface of the metal oxide material, reduce or eliminate the negative impact of the compound on the electron transport performance of the metal oxide material, thereby improving the performance stability of the electron functional layer, and further improving the optoelectronic performance, device life, and performance stability of the optoelectronic device.

[0310] The above has introduced in detail an optoelectronic device, a preparation method of the optoelectronic device, and an electronic device provided by the embodiments of the present application. Specific examples are used in this article to elaborate on the principle and implementation manner of the present application. The description of the above embodiments is only used to help understand the technical solution and its core idea of the present application; those of ordinary skill in the art should understand that they can still modify the technical solutions recorded in the foregoing embodiments, or perform equivalent replacements on some of the technical features; and these modifications or replacements do not cause the corresponding technical solutions to deviate from the scope of the technical solutions of the embodiments of the present application.

Claims

1. A compound, characterized in that, The compound has the structure shown by the following general formula (I): In general formula (I), R s , R t , R x and R y are each independently selected from hydrogen, deuterium, -NR z R m , halogen, hydroxy, carboxy, nitro, sulfo, mercapto, cyano, formyl, amido, an unsubstituted or at least one substituent-substituted C1-C30 aliphatic hydrocarbon group, an unsubstituted or at least one substituent-substituted C1-C30 aliphatic hydrocarbon oxy group, an unsubstituted or at least one substituent-substituted C3-C30 aliphatic cyclo hydrocarbon group, an unsubstituted or at least one substituent-substituted C3-C30 aliphatic heterocyclic hydrocarbon group, an unsubstituted or at least one substituent-substituted aryl group having 6 to 30 ring atoms, an unsubstituted or at least one substituent-substituted aryloxy group having 6 to 30 ring atoms, an unsubstituted or at least one substituent-substituted heteroaryl group having 5 to 30 ring atoms, or an unsubstituted or at least one substituent-substituted heteroaryloxy group having 5 to 30 ring atoms, or a combination of these groups; the heteroatoms in the aliphatic heterocyclic hydrocarbon group, the heteroaryl group and the heteroaryloxy group are each independently selected from one or more of N, S, O, P and Si, and the number of heteroatoms in the aliphatic heterocyclic hydrocarbon group, the heteroaryl group and the heteroaryloxy group are each independently selected from 1 to 20; Each occurrence of said substituent is independently selected from deuterium, -NR z R m , halogen, hydroxyl, carboxyl, nitro, sulfonic acid group, mercapto, cyano, aldehyde group, or amide group, or a combination of these groups; R z and R m are each independently selected from hydrogen, deuterium, an aliphatic hydrocarbon group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 ring atoms; n1 is selected from positive integers of 1 to 5.

2. The compound according to claim 1, wherein The compound has the structure shown by the following general formula (I-1): In the general formula (I-1), R1 is selected from an unsubstituted or at least one first group-substituted C1-C30 aliphatic hydrocarbon group, an unsubstituted or at least one first group-substituted C1-C30 aliphatic hydrocarbon oxy group, an unsubstituted or at least one first group-substituted C3-C30 aliphatic cyclo hydrocarbon group, an unsubstituted or at least one first group-substituted C3-C30 aliphatic heterocyclic hydrocarbon group, an unsubstituted or at least one first group-substituted aryl group with 6 to 30 ring atoms, an unsubstituted or at least one first group-substituted aryloxy group with 6 to 30 ring atoms, an unsubstituted or at least one first group-substituted heteroaryl group with 5 to 30 ring atoms, an unsubstituted or at least one first group-substituted heteroaryloxy group with 5 to 30 ring atoms, or a combination of these groups; Each occurrence of the first group is independently selected from hydrogen, deuterium, -NR z R m , halogen, hydroxyl, carboxyl, nitro, sulfonic acid group, mercapto, cyano, aldehyde group, or amide group, or a combination of these groups.

3. The compound according to claim 2, wherein In the general formula (I-1), R1 is selected from an unsubstituted or at least one first group-substituted C8-C30 aliphatic hydrocarbon group, an unsubstituted or at least one first group-substituted C8-C30 aliphatic hydrocarbon oxy group, an unsubstituted or at least one first group-substituted C8-C30 aliphatic cyclo hydrocarbon group, an unsubstituted or at least one first group-substituted C8-C30 aliphatic heterocyclic hydrocarbon group, an unsubstituted or at least one first group-substituted aryl group with 6 to 20 ring atoms, an unsubstituted or at least one first group-substituted aryloxy group with 6 to 20 ring atoms, an unsubstituted or at least one first group-substituted heteroaryl group with 5 to 20 ring atoms, an unsubstituted or at least one first group-substituted heteroaryloxy group with 5 to 20 ring atoms, or a combination of these groups.

4. The compound according to claim 2, wherein In the general formula (I-1), R1 is selected from an unsubstituted or at least one first group-substituted C15-C30 aliphatic hydrocarbon group.

5. A method for preparing a compound, characterized in that, The preparation method of the compound comprises the following steps: (A1) Performing a first amide coupling reaction on a first reaction system comprising phenylalanine and 2,3-diamino-3-oxopropionic acid to obtain intermediate 1; (A2) Performing a substitution reaction on a second reaction system comprising the intermediate 1 and substance A to obtain intermediate 2; and (A3) Performing a second amide coupling reaction on a third reaction system comprising the intermediate 2 and substance B to obtain the compound shown by the general formula (I-1); wherein, the intermediate 1 has the structure shown by the following formula (II): The substance A has the structure shown by the following formula (III): In the formula (III), X is selected from F, Cl, Br or I; The intermediate 2 has the structure shown by the following formula (IV): The substance B has the structure shown by the following formula (V): R1-NH2 (V).

6. The preparation method of the compound according to claim 5, characterized in that, In step (A1), the molar ratio of phenylalanine to 2,3-diamino-3-oxopropionic acid is 1:(1.0 - 1.5); and / or In step (A2), the molar ratio of the intermediate 1 to the substance A is 1:(0.1 - 0.3); and / or In step (A3), the molar ratio of the intermediate 2 to the substance B is 1:(1.0 - 1.2).

7. The preparation method of the compound according to claim 6, characterized in that, In step (A1), the first amide coupling reaction is carried out in an inert gas atmosphere and at 20°C - 25°C, and the reaction time of the first amide coupling reaction is 10 h - 20 h; and / or, the first reaction system further comprises a first catalyst, and the first catalyst comprises 1-hydroxybenzotriazole and 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride; and / or In step (A2), the substitution reaction is carried out in an inert gas atmosphere and at 60°C - 70°C, and the reaction time of the substitution reaction is 10 h - 12 h; and / or, the second reaction system further comprises an acid-binding agent; and / or In step (A3), the second amide coupling reaction is carried out in an inert gas atmosphere and at 20°C - 25°C, and the reaction time of the second amide coupling reaction is 10 h - 12 h; and / or, the second reaction system further comprises a second catalyst, and the second catalyst comprises 1-hydroxybenzotriazole and 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride.

8. A composite material, characterized in that, The composite material comprises a metal oxide material and a compound as described in any one of claims 1 to 4, or a compound prepared by the preparation method of the compound as described in any one of claims 5 to 7.

9. The composite material according to claim 8, wherein The composite material is composed of the metal oxide material and the compound; and / or The proportion of the mass of the compound in the total mass of the composite material is 0.5% - 1.5%; and / or The metal oxide material comprises at least one undoped first metal oxide and / or at least one doped second metal oxide; the first metal oxide is selected from ZnO, TiO2, SnO2, BaO, Ta2O3, Al2O3 or ZrO2, and / or the second metal oxide is the first metal oxide doped with a first doping element, and the first doping element is selected from one or more of Mg, Ca, Zr, W, Ga, Li, Al, Ti, Y, In and Sn, and the proportion of the molar amount of the first doping element in the total molar amount of the second metal oxide does not exceed 50%; and / or The metal oxide material is in the form of nanoparticles, and the average particle size of the metal oxide material is 2 nm - 15 nm; and / or The amide group in the compound forms a hydrogen bond with the hydroxyl group on the surface of the metal oxide material, and / or the hydrogen atom of the aromatic group in the compound is coordinately connected with the metal ion in the metal oxide material.

10. A thin film, characterized in that, The material of the thin film comprises a metal oxide material and a compound as described in any one of claims 1 to 4, or a compound prepared by the preparation method of the compound as described in any one of claims 5 to 7.

11. The thin film according to claim 10, characterized in that, The material of the thin film is composed of the metal oxide material and the compound; and / or The thin film is of a single-layer structure, and the proportion of the mass of the compound in the total mass of the thin film is 0.5% to 1.5%; alternatively, the thin film includes a first sub-layer and a second sub-layer arranged in a stacked manner, the material of the first sub-layer includes the metal oxide material, the material of the second sub-layer includes the compound, and the thickness ratio of the second sub-layer to the first sub-layer is 1:(1.5 to 5); and / or The metal oxide material includes at least one undoped first metal oxide and / or at least one doped second metal oxide; the first metal oxide is selected from ZnO, TiO2, SnO2, BaO, Ta2O3, Al2O3 or ZrO2, and / or the second metal oxide is the first metal oxide doped with a first doping element, and the first doping element is selected from one or more of Mg, Ca, Zr, W, Ga, Li, Al, Ti, Y, In and Sn, and the proportion of the molar amount of the first doping element in the total molar amount of the second metal oxide does not exceed 50%; and / or The metal oxide material is in the form of nanoparticles, and the average particle size of the metal oxide material is 2 nm to 15 nm; and / or The amide group in the compound forms a hydrogen bond with the hydroxyl group on the surface of the metal oxide material, and / or the hydrogen atom of the aromatic group in the compound is coordinately connected to the metal ion in the metal oxide material; and / or The average thickness of the thin film is 20 nm to 100 nm.

12. The thin film according to claim 10, characterized in that, The average thickness of the first sub-layer is 10 nm to 90 nm, and / or the average thickness of the second sub-layer is 5 nm to 15 nm.

13. An optoelectronic device, characterized in that, Comprising: A first electrode and a second electrode arranged opposite to each other; And A functional layer disposed between the first electrode and the second electrode; Wherein, the material of the functional layer includes the compound described in any one of claims 1 to 4, the compound prepared by the preparation method of the compound described in any one of claims 5 to 7, or the composite material described in claim 8 or 9, or the functional layer includes the thin film described in any one of claims 10 to 12.

14. The optoelectronic device according to claim 13, wherein The functional layer includes an electronic functional layer; wherein, the material of the electronic functional layer includes the compound described in any one of claims 1 to 4, or the compound prepared by the preparation method of the compound described in any one of claims 5 to 7, or the composite material described in claim 8 or 9, or the electronic functional layer includes the thin film described in any one of claims 10 to 12.

15. The optoelectronic device according to claim 13 or 14, characterized in that, The functional layer includes a light-emitting layer; the material of the light-emitting layer includes one or more of organic light-emitting materials and light-emitting quantum dots; the organic light-emitting materials are selected from 4,4'-bis(N-carbazolyl)-1,1'-biphenyl: tris[2-(p-tolyl)pyridineiridium(III), 4,4',4''-tris(carbazol-9-yl)triphenylamine: tris[2-(p-tolyl)pyridineiridium, diarylanthracene derivatives, stilbene aromatic derivatives, pyrene derivatives, fluorene derivatives, TBPe fluorescent materials, TTPX fluorescent materials, TBRb fluorescent materials, DBP fluorescent materials, delayed fluorescence materials, TTA materials, thermally activated delayed materials, polymers containing B-N covalent bonds, hybrid local charge transfer excited state materials, exciplex luminescent materials, polyacetylene and its derivatives, poly(phenylene) and its derivatives, polythiophene and its derivatives, polyfluorene and its derivatives; and / or, the light-emitting quantum dots are selected from one or more of single-component quantum dots, core-shell structure quantum dots, inorganic perovskite quantum dots, organic perovskite quantum dots, and organic-inorganic hybrid perovskite quantum dots, and the core-shell structure quantum dots include one or more shell layers;The material of the single-component quantum dots, the material of the core of the core-shell structure quantum dots, and the material of the shell of the core-shell structure quantum dots are each independently selected from at least one of II-VI group compounds, III-VI group compounds, III-V group compounds, IV-VI group compounds, or I-III-VI group compounds. Among them, the II-VI group compounds are selected from one or more of CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, HgS, HgSe, HgTe, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and HgZnSTe; and / or the III-V group compounds are selected from one or more of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, and InAlPSb; and / or the III-VI group compounds are selected from one or more of In2S3, In2Se3, InGaS3, and InGaSe3; and / or the IV-VI group compounds are selected from one or more of SnS, SnSe, SnTe, PbS, PbSe, PbTe, SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, SnPbSSe, SnPbSeTe, and SnPbSTe; and / or the I-III-VI group compounds are selected from one or more of AgInS, AgInS2, CuInS, CuInS2, AgGaS2, CuGaS2, CuGaO2, AgGaO2, AgAlO2, AgInGaS2, and CuInGaS2; and / or, the structural general formula of the inorganic perovskite quantum dots is AMX3, where A is Cs; + , M is a divalent metal cation, and M is selected from Pb 2+ , Sn 2+ , Cu 2+ , Ni 2+ , Cd 2+ , Cr 2+ , Mn 2+ , Co 2+ , Fe 2+ , Ge 2+ , Yb 2+ and Eu 2+ ; and / or, the structural general formula of the organic perovskite quantum dots is CMX3, where C is formamidinium; and / or, the structural general formula of the organic-inorganic hybrid perovskite quantum dots is BMX3, where B is an organic amine cation; and / or The functional layer includes a hole functional layer; the material of the hole functional layer includes one or more of an undoped first inorganic compound, a doped second inorganic compound, and an organic compound; wherein, the organic compound is selected from one or more of poly(3,4-ethylenedioxythiophene):poly(styrenesulfonic acid), copper phthalocyanine, titanium oxyphthalocyanine, 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinodimethane, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene, polypyrrole, polyaniline, 3-hexyl-substituted polythiophene, poly(9-vinylcarbazole), 4,4'-bis(9-carbazolyl)biphenyl, poly[bis(4-phenyl)(4-butylphenyl)amine], 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline], poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine)], poly[(N,N'-(4-butylphenyl)-N,N'-diphenyl-1,4-phenylenediamine)-ALT-(9,9-dioctylfluorenyl-2,7-diyl)], 4,4',4'-tris(N-3-methylphenyl-N-phenylamino)triphenylamine, 4,4',4''-tris(carbazol-9-yl)triphenylamine, 4,4',4'-tris(2-naphthylphenylamino)triphenylamine, N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine, N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine, N,N'-bis[4-(diphenylamino)phenyl]-N,N'-diphenylbenzidine, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-9,9-spirobifluorene-2,7-diamine, N2,N7-di-1-naphthyl-N2,N7-diphenyl-9,9'-spirobi[9H-fluorene]-2,7-diamine, poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine], and 2,2',7,7'-tetra[N,N-bis(4-methoxyphenyl)amino]-9,9'-spirobifluorene; and / or the undoped first inorganic compound is selected from one or more of graphene, C60, nickel oxide, molybdenum oxide, tungsten oxide, vanadium oxide, p-type gallium nitride, chromium oxide, copper oxide, copper sulfide, molybdenum sulfide, and tungsten sulfide; and / or the doped second inorganic compound is a host inorganic compound doped with a second doping element, the host inorganic compound is selected from one or more of graphene, C60, nickel oxide, molybdenum oxide, tungsten oxide, vanadium oxide, p-type gallium nitride, chromium oxide, copper oxide, copper sulfide, molybdenum sulfide, and tungsten sulfide, and the second doping element is selected from one or more of nickel, molybdenum, tungsten, vanadium, chromium, copper, and platinum group metal elements; and / or The materials of the first electrode and the second electrode independently include one or more of a metal, a carbon material, and a third metal oxide; wherein, the metal is selected from one or more of Al, Ag, Cu, Mo, Au, Ba, Pt, Ca, Ir, Ni, and Mg, and / or the carbon material is selected from one or more of graphite, carbon nanotubes, graphene, and carbon fiber, and / or the third metal oxide is selected from one or more of indium-doped tin oxide, fluorine-doped tin oxide, antimony-doped tin oxide, aluminum-doped zinc oxide, gallium-doped zinc oxide, indium-doped zinc oxide, magnesium-doped zinc oxide, aluminum-doped magnesium oxide, SnO2, ZnO, and In2O3.

16. The optoelectronic device according to claim 15, characterized in that, When the functional layer includes a light-emitting layer and the material of the light-emitting layer includes the light-emitting quantum dots, the electron functional layer includes a first sub-layer and a second sub-layer arranged in a stack, the material of the first sub-layer includes the metal oxide material, the material of the second sub-layer includes the compound, the thickness ratio of the second sub-layer to the first sub-layer is 1:(1.5 - 5), and the first sub-layer is closer to the light-emitting layer than the second sub-layer.

17. An electronic device, characterized in that, A photoelectric device comprising the photoelectric device according to any one of claims 13 to 16.

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