Organic compound, composite material, composition, film, preparation method and application

Abstract

The invention discloses an organic compound, a composite material, a composition, a film, a preparation method and application, and relates to the technical field of organic materials. The organic compound has a structure as shown in formula (I), in which X is selected from one of Cl, Br and I, and L is a linking group. The organic compound provided by the invention is a novel amphoteric organic compound which simultaneously has the characteristics of Lewis base and Lewis acid.

Description

Technical Field

[0001] This application relates to the field of organic materials technology, and in particular to an organic compound, composite material, composition, thin film, preparation method and application. Background Technology

[0002] Organic compounds are widely used in various fields, such as biology, medicine, and electronic devices. Among them, amphoteric organic compounds, which possess the properties of both Lewis bases and Lewis acids, have a wide range of applications due to their simultaneous presence of these characteristics. Summary of the Invention

[0003] In view of this, this application provides an organic compound, a composite material, a composition, a thin film, a method for preparation therefrom, and an application thereof.

[0004] The embodiments of this application are implemented as follows: an organic compound having the structure shown in formula (I):

[0005]

[0006] X is selected from one of Cl, Br, and I;

[0007] L is a linking group, selected from single bonds, unsubstituted or substituted C1-C bonds. 30 Alkylene, unsubstituted or substituted C1-C 30 alkenyl groups, unsubstituted or substituted C1-C 30 The ethynyl group, unsubstituted or substituted C1-C 30 One or more combinations of etheryl groups, wherein the substituted substituents include halogens, hydroxyl groups, silyl groups, C1-C1 groups, etc. 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 One or more of the following: alkylthio, aryl with 6 to 60 ring atoms, aryloxy with 6 to 60 ring atoms, and arylthio with 6 to 60 ring atoms.

[0008] Accordingly, embodiments of this application also provide a composite material, comprising a perovskite material and the aforementioned organic compound.

[0009] Accordingly, embodiments of this application also provide a composition comprising a perovskite material precursor, a solvent, and the aforementioned organic compound.

[0010] Accordingly, embodiments of this application also provide a perovskite thin film comprising the aforementioned composite material.

[0011] Accordingly, this application also provides a method for preparing a perovskite thin film, comprising the following steps:

[0012] Provide the composition;

[0013] The composition is deposited to obtain a wet film, and an antisolvent is added to the wet film to obtain a perovskite thin film.

[0014] Accordingly, this application also provides an optoelectronic device including the above-mentioned perovskite thin film.

[0015] Accordingly, embodiments of this application also provide a display device including the aforementioned optoelectronic device.

[0016] The organic compound described in this application is a novel amphoteric organic compound that simultaneously possesses the properties of a Lewis base and a Lewis acid. Attached Figure Description

[0017] To more clearly illustrate the technical solutions in the embodiments of this application, the accompanying drawings used in the description of the embodiments will be briefly introduced below. Obviously, the accompanying drawings described below are only some embodiments of this application. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0018] Figure 1 This is a flowchart illustrating a method for preparing an organic compound provided in an embodiment of this application;

[0019] Figure 2 This is a flowchart illustrating a method for preparing a perovskite thin film according to an embodiment of this application.

[0020] Figure 3 This is a schematic diagram of the structure of an optoelectronic device provided in an embodiment of this application;

[0021] Figure 4 This is a schematic diagram of another optoelectronic device provided in the embodiments of this application.

[0022] Figure label:

[0023] Optoelectronic device 100; anode 10; active layer 20; cathode 30; hole transport layer 40; electron transport layer 50; hole injection layer 60. Detailed Implementation

[0024] The technical solutions of the embodiments of this application will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some embodiments of this application, and not all embodiments. Based on the embodiments of this application, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of this application. Furthermore, it should be understood that the specific embodiments described herein are only for illustration and explanation of this application and are not intended to limit this application.

[0025] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. The terminology used herein in the specification of this invention is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. The term "and / or" as used herein includes any and all combinations of one or more of the associated listed items.

[0026] In this application, unless otherwise stated, directional terms such as "upper" and "lower" generally refer to the upper and lower positions of the device in its actual use or operating state, specifically the drawing directions in the accompanying drawings; while "inner" and "outer" refer to the outline of the device. Furthermore, in the description of this application, the term "comprising" means "including but not limited to". The terms first, second, third, etc., are used merely as illustrative purposes and do not impose numerical requirements or establish a numerical order.

[0027] In this application, "and / or" describes the relationship between related objects, indicating that three relationships can exist. For example, A and / or B can represent: A existing alone, A and B existing simultaneously, or B existing alone. A and B can be singular or plural.

[0028] In this application, "at least one" means one or more, and "more than one" means two or more. "At least one," "at least one of the following," or similar expressions refer to any combination of these items, including any combination of single or multiple items. For example, "at least one of a, b, or c," or "at least one of a, b, and c," can both mean: a, b, c, ab (i.e., a and b), ac, bc, or abc, where a, b, and c can be single or multiple.

[0029] In this application, the term "on" forming another layer on a certain layer is a broad concept. It can mean that the formed another layer is adjacent to a certain layer, or it can mean that there are other spacer structures between the other layer and the certain layer. For example, when a cathode is formed "on" the first carrier functional layer, the term "on" can mean that the formed cathode is adjacent to the first carrier functional layer, or it can mean that there are other spacer structures between the cathode and the first carrier functional layer, such as a light-emitting layer.

[0030] Various embodiments of this application may exist in the form of a range; it should be understood that the description in the form of a range is merely for convenience and brevity and should not be construed as a hard limitation on the scope of this application; therefore, it should be considered that the range description has specifically disclosed all possible sub-ranges and single numerical 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 range, such as 1, 2, 3, 4, 5, and 6, regardless of the range. Furthermore, whenever a numerical range is referred to herein, it means including any referenced number (fraction or integer) within the referred range.

[0031] In this application, aromatic groups, aromatic families, and aromatic ring systems have the same meaning and can be used interchangeably.

[0032] In this application, heteroaromatic groups, heteroaromatic families, and heteroaromatic ring systems have the same meaning and can be used interchangeably.

[0033] In this application, "aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing one hydrogen atom. It can be a monocyclic aryl, a fused-ring aryl, or a polycyclic aryl, and for polycyclic rings, at least one is an aromatic ring system. For example, "substituted or unsubstituted aryl having 6 to 40 ring atoms" means an aryl containing 6 to 40 ring atoms, and the aryl may optionally be further substituted. Preferably, it is a substituted or unsubstituted aryl having 6 to 30 ring atoms; more preferably, it is a substituted or unsubstituted aryl having 6 to 18 ring atoms; particularly preferably, it is a substituted or unsubstituted aryl having 6 to 14 ring atoms, and the aryl may optionally be further substituted. Suitable examples include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, fluoranyl, triphenylene, pyrene, perylene, tetraphenyl, fluorenyl, dinaphthylphenyl, acenaphthyl, and their derivatives. Understandably, 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), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, and diaryl ether systems should also be included in the definition of aryl.

[0034] In this application, "heteroaryl or heteroaromatic group" refers to an aryl group in which at least one carbon atom is replaced by a non-carbon atom, which can be an N atom, O atom, S atom, Si atom, P atom, etc. For example, "substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms" refers to a heteroaryl group having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms, and the heteroaryl group may optionally be further substituted; suitable examples include, but are not limited to: thiophene, furanyl, pyrrole, diazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidinyl, etc. Triazinyl, acridineyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridinylpyrimidineyl, pyridinylpyrazinyl, benzothiopheneyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrololyl, thienopyrrololyl, thienopyrrololyl, furanolololyl, furanolofuranyl, thienofuranyl, benzoisoxazolyl, benzoisothiazolyl, benzoimidazolyl, o-diazonyl, phenanthridineyl, primidyl, quinazolinoneyl, dibenzothiopheneyl, dibenzofuranyl, carbazoleyl and their derivatives.

[0035] In this application, "alkyl" can mean straight-chain, branched, and / or cyclic alkyl. The number of carbon atoms in an alkyl group can be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Phrases containing this term, such as "C 1-9"Alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, and each time it appears, it can independently be a C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl, or C9 alkyl. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, etc. tert-amyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl The compounds include 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-hepta ...

[0036] In this application, "-C" n H 2n+1 "Unless otherwise specified or limited, it indicates a straight-chain alkyl group. For example, -C4H9 indicates n-butyl."

[0037] In this application, "alkoxy" refers to a group with the structure "-O-alkyl", that is, an alkyl group as defined above that is attached to other groups via an oxygen atom. Suitable examples of phrases containing this term include, but are not limited to: methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt), and tert-butoxy (-OC(CH3)3 or -OtBu).

[0038] The terms “combinations thereof,” “any combination thereof,” and “any combination thereof” as used in this application include all suitable combinations of any two or more of the listed items.

[0039] In recent years, with the rapid development of display technology and lighting applications, light sources with characteristics such as low energy consumption, high efficiency, tunable spectrum, and flexibility have received widespread attention. Against this backdrop, perovskite light-emitting diodes (PeLEDs) have emerged as a novel optoelectronic material, attracting considerable interest from researchers. Compared to other light-emitting materials, perovskites possess high quantum efficiency, narrow emission spectra, and tunable color output, making PeLEDs promising for a wide range of applications, including solar cells and diodes.

[0040] The main component of PeLED is perovskite material, which is a class of compounds with an ABX3 lattice structure, where A is usually an organic or inorganic cation, such as methylammonium (CH3NH4+). 3+ MA (abbreviated as MA), cesium ion (Cs) + ) etc.; the B site is a metal cation, such as lead (Pb). 2+ ), Tin (Sn) 2+ ) etc.; the X position is a halide anion, such as iodine (I) - ), bromine (Br) - Depending on the different combinations of constituent elements, PeLED can achieve light output in a variety of colors.

[0041] However, since the metal halide perovskite material used in PeLED is an ionic soft crystal with poor stability, it is easily affected by light, heat or electrical bias, which can lead to the generation and long-distance migration of ionic defects. This can further lead to element redistribution, deep defect formation, and even unpredictable chemical reactions, ultimately greatly reducing the lifespan and stability of the device.

[0042] Among the aforementioned ions, the two most prominent defects are in metallic Pb. 2+ Vacancy defects formed by shedding and I - The number and migration of electronic defects formed by ion shedding directly determine the lifetime and long-term stability of PeLED devices. Existing technical solutions mainly fall into two categories: 1. Optimizing composition and crystallization to reduce defects and minimize ion migration channels; 2. Introducing small organic molecules with Lewis acid or Lewis base properties to passivate hole / electron defects. The first approach requires highly sophisticated perovskite crystal preparation, making the process complex and difficult. The second approach, due to the complexity and diversity of materials, often only passivates single defects, limiting its effectiveness in improving long-term device stability. Therefore, to ensure high lifetime and long-term photoelectric stability, it is necessary to find a material that can simultaneously passivate both electron and hole defects in halides.

[0043] The technical solution of this application is as follows:

[0044] In a first aspect, embodiments of this application provide an organic compound having the structure shown in formula (I):

[0045]

[0046] X is selected from any one of Cl, Br, and I;

[0047] L is a linking group, which can be selected from, but is not limited to, single bonds, unsubstituted or substituted C1-C bonds. 30 Alkylene, unsubstituted or substituted C1-C 30 alkenyl groups, unsubstituted or substituted C1-C 30 The ethynyl group, unsubstituted or substituted C1-C 30 One or more combinations of etheryl groups, wherein the substituted substituents include halogens, hydroxyl groups, silyl groups, C1-C1 groups, etc. 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 One or more of the following: alkylthio, aryl with 6 to 60 ring atoms, aryloxy with 6 to 60 ring atoms, and arylthio with 6 to 60 ring atoms.

[0048] The amine group in the organic compound described in this application exhibits Lewis base properties; the F atom in the organic compound has a stronger electronegativity than X, causing electrons from X to shift towards the F atom, resulting in σ vacancies on the X atom, which exhibit electron acceptor properties, i.e., Lewis acid properties. Therefore, the organic compound described in this application possesses both Lewis base and Lewis acid properties, and is an amphoteric organic compound.

[0049] In the organic compound described in this application, the two sites adjacent to O on the benzene ring are connected to F atoms. This ensures consistency with the atoms adjacent to X on the benzene ring, guaranteeing that the atoms connected to F on the benzene ring, excluding X, have the same electronegativity as F. This effectively prevents electron shifts between the two F atoms adjacent to X, avoiding disruption of the electron cloud arrangement of the F atoms adjacent to X, and facilitating the generation of σ vacancies on the X atom. Furthermore, the direct connection of F and X to the benzene ring also promotes the generation of σ vacancies on the X atom.

[0050] The amine group in the organic compound described in this application is a monoamine group (-NH2), which has strong Lewis base properties. Furthermore, the linking group L between -NH2 and O in the organic compound does not contain a carbonyl group (-C=O). Therefore, there is no phenomenon where the electronegativity of O in the C=O bond is greater than that of N in the amino group, preventing the amino group from effectively functioning as a Lewis base, thereby further enhancing the Lewis base properties of the organic compound.

[0051] In some embodiments, L may be selected from, but is not limited to, single bonds, unsubstituted or substituted C1-C bonds. 20 Alkylene, unsubstituted or substituted C1-C 20 alkenyl groups, unsubstituted or substituted C1-C 20 The ethynyl group, unsubstituted or substituted C1-C 20 One or more combinations of etheryl groups, wherein the substituted substituents include halogens, hydroxyl groups, C1-C2 groups. 15 Alkyl, C1-C 15 Alkoxy, C1-C 15 One or more of the following: alkylthio, aryl with 6 to 30 ring atoms, aryloxy with 6 to 30 ring atoms, and arylthio with 6 to 30 ring atoms.

[0052] Furthermore, in some embodiments, L may be selected from, but is not limited to, single bonds, unsubstituted or substituted C1-C bonds. 15 Alkylene, unsubstituted or substituted C1-C 15 alkenyl groups, unsubstituted or substituted C1-C 15 The ethynyl group, unsubstituted or substituted C1-C 15 One or more combinations of etheryl groups, wherein the substituted substituents include halogens, hydroxyl groups, C1-C2 groups. 10 Alkyl, C1-C 10 Alkoxy, C1-C 10 One or more of the following: alkylthio, aryl with 6 to 20 ring atoms, aryloxy with 6 to 20 ring atoms, and arylthio with 6 to 20 ring atoms.

[0053] Furthermore, in some embodiments, L may be selected from, but is not limited to, single bonds, unsubstituted or substituted C1-C bonds. 15 Alkylene, unsubstituted or substituted C1-C 15 alkenyl groups, unsubstituted or substituted C1-C 15 One or more combinations of alkynyl groups, wherein the substituted substituents include halogens, hydroxyl groups, C1-C2 groups. 10 Alkyl, C1-C 10 Alkoxy, C1-C 10One or more of the following: alkylthio, aryl with 6 to 20 ring atoms, aryloxy with 6 to 20 ring atoms, and arylthio with 6 to 20 ring atoms.

[0054] Furthermore, in some embodiments, L may be selected from, but is not limited to, single bonds, unsubstituted or substituted C1-C bonds. 15 Alkylene, wherein the substituted substituents include halogens, hydroxyl groups, C1-C2 groups. 10 Alkyl, C1-C 10 Alkoxy, C1-C 10 One or more of the following: alkylthio, aryl with 6 to 20 ring atoms, aryloxy with 6 to 20 ring atoms, and arylthio with 6 to 20 ring atoms.

[0055] Furthermore, in some embodiments, L may be selected from, but is not limited to, single bonds, unsubstituted or substituted C1-C bonds. 10 Alkylene, wherein the substituted substituents include hydroxyl, C1-C2, ... 10 One or more of alkyl groups and aryl groups having 6 to 20 cyclic atoms.

[0056] In some embodiments, the organic compound has the structures shown in formulas (I-1) to (I-4):

[0057]

[0058] As an example, the organic compound may be selected from, but is not limited to, any one of the compounds shown in formulas M1 to M12:

[0059]

[0060]

[0061] Secondly, embodiments of this application also provide a method for preparing an organic compound, wherein the synthetic route of the organic compound is as follows:

[0062]

[0063] Please refer to the following: Figure 1 The method for preparing the organic compound includes the following steps:

[0064] Step S11: Mix the alkanolamine compound with di-tert-butyl carbonate and carry out an acid-base reaction to obtain compound 1;

[0065] Step S12: Mix compound 1 and compound 2 to carry out a substitution reaction to obtain compound 3;

[0066] Step S13: Mix compound 3 and compound 4 and carry out acid hydrolysis to obtain an organic compound.

[0067] In step S11:

[0068] The L in the alkanolamine compound is as described above and will not be repeated here.

[0069] In some embodiments, the alkanolamine compound includes, but is not limited to, one or more of ethanolamine, DL-2-amino-3-methyl-1-butanol, 2-amino-1-phenylethanol, and 3-amino-1,2-propanediol.

[0070] The molar ratio of the alkanolamine compound to the di-tert-butyl carbonate is (1.03 to 1.1):1, for example, 1.03:1, 1.04:1, 1.05:1, 1.06:1, 1.07:1, 1.08:1, 1.09:1, 1.1:1, etc.

[0071] In some embodiments, the reaction temperature of the acid-base reaction is -5 to 0°C, for example, -5°C, -4.5°C, -4°C, -3.5°C, -3°C, -2.5°C, -2°C, -1.5°C, -1°C, -0.5°C, 0°C, etc. Within this temperature range, it is beneficial for ethanolamine to react safely, fully, and effectively with di-tert-butyl carbonate.

[0072] In some embodiments, the acid-base reaction is carried out under a first catalyst. The first catalyst may be selected from, but is not limited to, nitrogen-containing organic bases, including but not limited to, one or more of triethylamine (TEA), pyridine, N,N-dimethylaniline (DMBA), N,N-dimethylformamide (DMF), N,N-dimethylformic anhydride (DMA), N,N-dimethylacetamide (DMAc), and N,N-dimethylpropionamide (DMAP).

[0073] In step S12:

[0074] In some embodiments, the molar ratio of compound 1 to compound 2 is 1:(1.2 to 1.3), for example, 1:1.2, 1:1.21, 1:1.22, 1:1.23, 1:1.24, 1:1.25, 1:1.26, 1:1.27, 1:1.28, 1:1.29, 1:1.3, etc.

[0075] The substitution reaction is carried out in the presence of a second catalyst. In some embodiments, the second catalyst includes, but is not limited to, cesium carbonate.

[0076] In some embodiments, the reaction temperature of the substitution reaction is 75 - 85 °C, such as 75 °C, 76 °C, 77 °C, 78 °C, 79 °C, 80 °C, 81 °C, 82 °C, 83 °C, 84 °C, 85 °C, etc. Within this temperature range, it is beneficial for the full and effective reaction of Compound 1 and Compound 2.

[0077] In step S13:

[0078] Compound 4 can be selected from but not limited to one or more of hydroiodic acid (HI), hydrofluoric acid (HF), and trifluoroacetic acid (TFA). Compound 4 can undergo an acidolysis reaction with Compound 3 to release an amino group and generate the organic compound.

[0079] In some embodiments, the molar ratio of Compound 4 to Compound 3 is (2 - 2.5):1, such as 2.1:1, 2.2:1, 2.3:1, 2.4:1, 2.5:1, etc.

[0080] In some embodiments, the temperature of the acidolysis reaction is 45 - 55 °C, such as 45 °C, 46 °C, 48 °C, 50 °C, 52 °C, 53 °C, 55 °C, etc., and the reaction time of the acidolysis reaction is 0.8 - 1.2 h, such as 0.8 h, 0.9 h, 1.0 h, 1.1 h, 1.2 h, etc. Within this temperature and time range, it is beneficial for the rapid and effective progress of the acidolysis reaction.

[0081] In a third aspect, the embodiments of the present application further provide a composite material, including a perovskite material and the organic compound described above.

[0082] In some embodiments, the organic compound is coordinately connected to the perovskite material. In other words, the organic compound is a ligand coordinately connected to the surface of the perovskite material.

[0083] In some embodiments, the chemical formula of the metal halide perovskite material is ABI a X’ b , where 0 < a ≤ 3 and 0 ≤ b < 3. A is an organic amine cation or an inorganic cation. The organic amine cation can be methylammonium (CH3NH 3+ , abbreviated as MA), CH3(CH2) n-2 NH3 + or [NH3(CH2) n NH3] 2+ , where n ≥ 2, and the inorganic cation can be Cs + . B is a metal cation and can be selected from but not limited to Pb 2+ . The X’ position is a halogen anion and can be selected from but not limited to chloride ion (Cl - ), bromide ion (Br- One or more of the following.

[0084] As an example, 'a' can be 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2.0, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, 3, etc.

[0085] As an example, b can be 0, 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2.0, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, etc.

[0086] As an example, the ABI a X' b For ABI 0.3 Br 2.7 ABI3, etc.

[0087] In some embodiments, the molar ratio of the organic compound to the perovskite material in the composite material is (0.05–0.09):1, for example, 0.05:1, 0.055:1, 0.06:1, 0.065:1, 0.07:1, 0.075:1, 0.08:1, 0.085:1, 0.09:1, etc. Within this range, the composite material can possess high stability and luminescent properties.

[0088] In the composite material described in this application, the surface of the perovskite material is connected to the organic compound described in this application. The amine group in the organic compound has strong Lewis base properties, which can effectively coordinate with the metal ion vacancies in the perovskite material to form coordinate bonds, thereby achieving vacancy passivation and preventing metal ion detachment. The σ vacancy generated after the electron cloud of the halogen atom X and the adjacent F atom in the organic compound is a Lewis acid group. The X atom can accept I atoms from the perovskite material. - The electrons of ions are used to form coordination bonds, passivating electronic defects in perovskite materials and allowing I to passivate the perovskite material. - Ions are anchored to the surface of perovskite materials, thereby effectively suppressing Ig. - Ion exfoliation. Thus, the organic compound described in this application can form two strong coordination interactions with the perovskite material, thereby attaching to the perovskite structure and simultaneously passivating vacancy defects of metal ions and Ig. -The electronic defects of ions effectively suppress the shedding and migration of ions in perovskite materials, thereby effectively improving the stability and luminescence properties of perovskite materials.

[0089] Understandably, the greater the difference in electronegativity between X and F in the organic compound, the stronger the σ vacancy formed, and the stronger the coordination bond formed between the organic compound and the perovskite material.

[0090] Furthermore, since the linking group L between -NH2 and O in the organic compound does not contain a carbonyl group (-C=O), when using the organic compound to passivate / modify perovskite materials, there is no phenomenon where the amino group cannot play the role of a Lewis base because the electronegativity of O in the C=O bond is greater than that of N in the amino group, thus competing with N during perovskite passivation. Therefore, the organic compound described in this application can effectively coordinate with the metal ion vacancies in the perovskite material to form coordinate bonds, achieving vacancy passivation and preventing metal ion detachment.

[0091] Fourthly, embodiments of this application also provide a composition comprising a perovskite material precursor, a solvent, and the organic compound described above.

[0092] The perovskite material precursor is a known precursor used to prepare the perovskite material described above. In some embodiments, the perovskite material precursor is a metal halide perovskite material precursor.

[0093] In some embodiments, the metal halide perovskite material precursor includes YB1X1, YX2, and B2X3. Wherein, Y is an organic amine cation as described above, B1 and B2 are each independently a metal cation as described above, and X1, X2, and X3 are each independently selected from the halide anions described above.

[0094] In some embodiments, the molar ratio of YB1X1, YX2, and B2X3 in the metal halide perovskite material precursor is (0.6–0.9):(0.1–0.4):1, for example, 0.6:0.1:1, 0.7:0.1:1, 0.8:0.1:1, 0.9:0.1:1, 0.6:0.2:1, 0.7:0.2:1, 0.8:0.2:1, 0.9:0.2:1, 0.6:0.3:1, 0.7:0.3:1, 0.8:0.3:1, 0.9:0.3:1, 0.6:0.4:1, 0.7:0.4:1, 0.8:0.4:1, and 0.9:0.4:1. Within this range, it is beneficial to prepare perovskite materials with good crystallinity, stability, and photoelectric properties.

[0095] In some embodiments, the molar ratio of the organic compound to the perovskite precursor is (0.05–0.09):2, for example, 0.05:2, 0.06:2, 0.07:2, 0.08:2, 0.09:2, etc. Within this ratio range, the perovskite material surface in the prepared composite material can have fewer defects, resulting in higher stability and photoelectric properties.

[0096] In some embodiments, the solvent includes, but is not limited to, one or more of N,N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), methanol, ethanol, isopropanol, 1-butanol, 1-pentanol, tetramethylethylenediamine (TMEDA), n-butyl acetate, dibutyl phthalate, and acetone.

[0097] In at least one embodiment, the solvent is a mixed solvent formed by DMF and DMSO. Further, in at least one embodiment, the volume ratio of DMF to DMSO in the mixed solvent is 4:1.

[0098] Fifthly, embodiments of this application also provide a perovskite thin film, including the composite material described above.

[0099] For the sixth aspect, please refer to Figure 2 This application also provides a method for preparing a perovskite thin film, comprising the following steps:

[0100] Step S21: Provide the composition described above;

[0101] Step S22: Deposit the composition to obtain a wet film, add an antisolvent to the wet film to nucleate and crystallize the perovskite, and coordinate the organic compound to the surface of the perovskite material to obtain a perovskite thin film.

[0102] It is understood that when the composition is deposited to obtain a wet film, the composition is deposited on a substrate, which is a substrate known for preparing thin films.

[0103] In some embodiments, the antisolvent may be one or more of toluene, dimethyl ethyl carbonate (EMC), ethyl acetate (EA), and n-octane. The antisolvent facilitates the crystallization of perovskite to obtain perovskite materials.

[0104] In some embodiments, the volume ratio of the composition to the antisolvent is 1:(10-30), for example, 1:10, 1:12, 1:13, 1:15, 1:16, 1:18, 1:20, 1:22, 1:24, 1:25, 1:27, 1:28, 1:29, 1:30, etc. This facilitates the crystallization of perovskite to obtain perovskite materials.

[0105] In some embodiments, a heat treatment is further included after obtaining the wet film and before obtaining the perovskite thin film.

[0106] It is understood that there is no restriction on the order of the heat treatment and the addition of the antisolvent to the wet film; the heat treatment can be performed at any time between obtaining the wet film and obtaining the perovskite thin film. In other words, the heat treatment can be performed before, during, or after the addition of the antisolvent.

[0107] In some embodiments, the heat treatment temperature is 75–85°C, for example, 75°C, 76°C, 77°C, 78°C, 79°C, 80°C, 81°C, 82°C, 83°C, 84°C, 85°C, etc., and the heat treatment time is 10–20 min, for example, 10 min, 11 min, 12 min, 13 min, 14 min, 15 min, 16 min, 17 min, 18 min, 19 min, 20 min, etc. Within this temperature and time range, it is beneficial to prepare perovskite materials with good crystallinity, and it is also beneficial for the organic compound to coordinate and connect to the perovskite material, thereby facilitating the preparation of perovskite thin films with good stability and photoelectric properties.

[0108] It is understood that the perovskite thin film prepared by the method described in this application includes the composite material mentioned above.

[0109] The perovskite thin film prepared by the method described in this application has an organic compound coordinated to the surface of the perovskite material. The amine group in this organic compound exhibits Lewis base characteristics, enabling it to coordinate with metal ion vacancies in the perovskite material, forming coordinate bonds to achieve vacancy passivation and prevent metal ion detachment. The σ vacancies generated by the rearrangement of the electron clouds between the halogen atom X and the adjacent F atom in the organic compound are Lewis acid groups. The X atom can accept electrons from halide ions in the perovskite material, forming coordinate bonds to passivate electronic defects in the perovskite material, thus anchoring the halide ions to the surface of the perovskite material and effectively inhibiting halide ion detachment. In this way, the organic compound described in this application can form two strong coordination interactions with the perovskite material, thus attaching to the perovskite structure. This allows for the simultaneous passivation of both metal ion vacancy defects and halide ion electronic defects on the perovskite material surface, effectively inhibiting ion detachment and migration, and consequently improving the stability and luminescent properties of the perovskite material.

[0110] Seventhly, embodiments of this application also provide an application of the composite material or the perovskite thin film described above in the optoelectronic field.

[0111] For the eighth aspect, please refer to Figure 3 This application provides an optoelectronic device 100, which includes the composite material described above, or the optoelectronic device 100 includes the perovskite thin film described above.

[0112] In some embodiments, the optoelectronic device 100 includes an anode 10, an active layer 20, and a cathode 30 stacked sequentially. The active layer 20 is made of the composite material described above, or the active layer 20 is a perovskite thin film described above.

[0113] In some embodiments, the thickness of the active layer 20 ranges from 35 to 45 nm.

[0114] It is understood that, in at least some embodiments, the active layer may be a light-emitting layer or a photoelectric conversion layer.

[0115] The optoelectronic device 100 described in this application includes the composite material, in which the surface of the perovskite material in the composite material is coordinated with the organic compound described above. The organic compound can simultaneously passivate the vacancy defects of metal ions and the electronic defects of halide ions on the surface of the perovskite material, effectively suppressing the shedding and migration of halide ions in the perovskite material, thereby effectively improving the stability and luminescence performance of the perovskite material, and thus effectively improving the optoelectronic performance, long-term stability and lifespan of the optoelectronic device 100.

[0116] Please see Figure 4 The optoelectronic device 100 further includes a hole transport layer 40, which is located between the active layer 20 and the anode 10.

[0117] The optoelectronic device 100 further includes an electron transport layer 50, which is disposed between the electron transport layer 50 and the hole transport layer 40.

[0118] In some embodiments, the optoelectronic device 100 further includes a hole injection layer 60 disposed between the anode 10 and the hole transport layer 40.

[0119] The anode 10 and the cathode 30 are anodes and cathodes known in the art for use in optoelectronic devices. For example, they can be independently, but are not limited to, doped metal oxide electrodes, composite electrodes, graphene electrodes, carbon nanotube electrodes, elemental metal electrodes, or alloy electrodes. The material of the doped metal oxide electrode can be, but is not limited to, one or more of indium-doped tin oxide (ITO), fluorine-doped tin oxide (FTO), antimony-doped tin oxide (ATO), aluminum-doped zinc oxide (AZO), gallium-doped zinc oxide (GZO), indium-doped zinc oxide (IZO), magnesium-doped zinc oxide (MZO), aluminum-doped magnesium oxide (AMO), and cadmium-doped zinc oxide. The composite electrode is an electrode formed by stacking two or more layers of conductive materials, such as AZO / Ag / AZO, AZO / Al / AZO, ITO / Ag / ITO, ITO / Al / ITO, ZnO / Ag / ZnO, ZnO / Al / ZnO, TiO2 / Ag / TiO2, TiO2 / Al / TiO2, ZnS / Ag / ZnS, ZnS / Al / ZnS, Ca / Al, LiF / Ca, LiF / Al, BaF2 / Al, CsF / Al, CaCO3 / Al, BaF2 / Ca / Al, etc., where " / " indicates a stacked structure. For example, AZO / Ag / AZO represents a composite electrode comprising sequentially stacked AZO, Ag, and AZO layers. The material of the elemental metal electrode may include, but is not limited to, one or more of Ag, Ni, Pt, Au, Ir, Cu, Mo, Al, Ca, Mg, and Ba. The alloy electrodes include, but are not limited to, one or more of Au:Mg alloy electrodes and Ag:Mg alloy electrodes.

[0120] In some embodiments, the anode is an electrode with a relatively high work function, such as, but not limited to, a doped metal oxide electrode with a relatively high work function, a metal element electrode with a relatively high work function, and a carbon nanotube electrode. The metal element electrode with the high work function can be selected from, but is not limited to, Ni, Pt, Au, Ag, Ir, etc.

[0121] In some embodiments, the cathode is an electrode with a relatively low work function, such as, but not limited to, a metallic elemental electrode, a composite electrode, and an alloy electrode with a relatively low work function. The metallic elemental electrode with a relatively low work function can be Ca, Ba, Al, Mg, etc. The composite electrode with a relatively low work function can be Ca / Al, LiF / Ca, LiF / Al, BaF2 / Al, CsF / Al, CaCO3 / Al, BaF2 / Ca / Al, etc. The alloy electrode with a relatively low work function can be Au:Mg and Ag:Mg, etc.

[0122] The hole transport layer 40 is made of materials known in the art for hole transport layers, such as, but not limited to, 4,4'-N,N'-dicarbazolyl-biphenyl (CBP), poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine] (PTAA), N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (α-NPD), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TPD), poly(N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)biphenylamine) (Poly-TPD), N,N'-bis(3- 4,4'-bis(phenyl)-spiro(spiro-TPD), N,N'-bis(4-(N,N'-diphenyl-amino)phenyl)-N,N'-diphenylbenzidine (DNTPD), 4,4',4'-tris(N-carbazolyl)-triphenylamine (TCTA), 4,4',4'-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (m-MTDATA), poly[(9,9'-dioctylfluorene-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine))](TFB), poly(N-vinylcarbazole) (PVK) and its derivatives, N,N'-bis(1-naphthyl)-N,N'-diphenyl-1 1'-Biphenyl-4-4'-diamine (NPB), spiroNPB, poly(phenylenevinylene) (PPV), poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylenevinylene] (MEH-PPV), poly[2-methoxy-5-(3',7'-dimethyloctyloxy)-1,4-phenylenevinylene] (MOMO-PPV), 2,2',7,7'-tetratetra[N,N-di(4-methoxyphenyl)amino]-9,9'-spirodifluorene (spiro-omeTAD), 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TAPC), 1,3-bis(carbazole-9-yl)benzene (MCP) The following are included: polyaniline, polypyrrole, poly(p-)phenylenevinylene, aromatic tertiary amine, polynuclear aromatic tertiary amine, 4,4'-bis(p-carbazolyl)-1,1'-biphenyl compounds, N,N,N',N'-tetraarylbenzidine, PEDOT:PSS and its derivatives, polymethacrylate and its derivatives, poly(9,9-octylfluorene) and its derivatives, poly(spirofluorene) and its derivatives, doped graphene, undoped graphene, C60, doped or undoped NiO, doped or undoped MoO3, doped or undoped WO3, doped or undoped V2O5, doped or undoped p-type gallium nitride, doped or undoped CrO3, and doped or undoped CuO.

[0123] The electron transport layer 50 is made of one or more inorganic and organic electron transport materials. The inorganic electron transport material includes one or more of metal oxides, doped metal oxides, group IIB-VIA semiconductor materials, group IIIA-VA semiconductor materials, and group IB-IIIA-VIA semiconductor materials. The metal oxide includes one or more of ZnO, TiO2, SnO2, ZrO2, and Ta2O5. The doped metal oxide includes one or more of ZnO, TiO2, SnO2, ZrO2, Ta2O5, and Al2O3. The dopants in the oxides include one or more of Al, Mg, Li, Mn, Y, La, Cu, Ni, Zr, Ce, In, Ga, and Sn; the IIB-VIA group semiconductor materials include one or more of ZnS, ZnSe, and CdS; the IIIA-VA group semiconductor materials include one or more of InP and GaP; the IB-IIIA-VIA group semiconductor materials include one or more of CuInS and CuGaS; and the organic electron transport materials include one or more of quinoxaline compounds, imidazole compounds, triazine compounds, fluorene-containing compounds, and hydroxyquinoline compounds.

[0124] The material of the hole injection layer 60 can also be a material known in the art for hole injection layers, such as, but not limited to, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzophenanthrene (HAT-CN), PEDOT, PEDOT:PSS, PEDOT:PSS derivatives doped with s-MoO3 (PEDOT:PSS:s-MoO3), 4,4',4'-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (m-MTDATA), tetracyanoquinone dimethyl ether (F4-TCQN), copper phthalocyanine, nickel oxide, molybdenum oxide, tungsten oxide, vanadium oxide, molybdenum sulfide, tungsten sulfide, and copper oxide.

[0125] In some embodiments, the thickness of the anode 10 ranges from 100 to 110 nm.

[0126] In some embodiments, the thickness of the cathode 30 ranges from 90 to 100 nm.

[0127] In some embodiments, the thickness of the hole transport layer 40 ranges from 25 to 30 nm.

[0128] In some embodiments, the thickness of the electron transport layer 50 ranges from 30 to 35 nm.

[0129] In some embodiments, the thickness of the hole injection layer 60 ranges from 20 to 25 nm.

[0130] It is understood that the optoelectronic device 100 may also be provided with some functional layers that are conventionally used in optoelectronic devices and help to improve the performance of optoelectronic devices, such as electron blocking layer, hole blocking layer, electron injection layer, etc.

[0131] It is understood that the materials of each layer of the optoelectronic device 100 can be adjusted according to the light emission requirements of the optoelectronic device 100.

[0132] In some embodiments, the optoelectronic device 100 further includes a substrate disposed on the side of the anode 10 away from the active layer 20, or the substrate disposed on the side of the cathode 30 away from the active layer 20.

[0133] The substrate can be a rigid substrate or a flexible substrate. In some embodiments, the substrate material may include, but is not limited to, one or more of glass, silicon wafer, polycarbonate, polymethyl methacrylate, polyethylene terephthalate, polyethylene naphthalate, polyamide, and polyethersulfone.

[0134] It is understood that the optoelectronic device 100 can be an upright optoelectronic device or an inverted optoelectronic device.

[0135] In some embodiments, the optoelectronic device 100 described in this application may be a perovskite light-emitting diode. It is understood that in other embodiments, the optoelectronic device 100 described in this application may also be an optoelectronic device comprising a perovskite thin film, such as a solar cell.

[0136] Ninthly, this application also relates to a display device, the display device including the optoelectronic device 100.

[0137] The display device can be any electronic product with display function, including but not limited to smartphones, tablets, laptops, digital cameras, digital camcorders, smart wearable devices, smart weighing scales, in-vehicle displays, televisions, or e-book readers. Among them, smart wearable devices can be, for example, smart bracelets, smartwatches, virtual reality (VR) headsets, etc.

[0138] The present application will be specifically described below through specific embodiments. These embodiments are only some embodiments of the present application and are not intended to limit the present application. Unless otherwise specified, the raw materials used in the following embodiments are all commercially available products.

[0139] Organic compound Example 1

[0140] The synthetic route of organic compound M1 in this embodiment is as follows:

[0141]

[0142] Step S11: Add 4 mL (66.3 mmol) of ethanolamine and 200 mL of dichloromethane (DCM) to a 500 mL round-bottom flask; then add 13.8 g (137.2 mmol) of triethylamine (TEA) to the solution and stir at 0 °C; slowly add 13.49 g (61.9 mmol) of di-tert-butyl carbonate, transfer the flask to room temperature and turn on the air; stir the reaction at room temperature overnight; then transfer the entire contents of the flask to a 1 L separating funnel and add 300 mL of saturated ammonium chloride solution; shake the funnel to separate the layers and discard the aqueous layer; wash the DCM layer twice with 300 mL of saturated ammonium chloride solution each time; then dry the organic phase on MgSO4 and concentrate under vacuum to obtain a clear oil phase product compound 1 (5.7 g, yield 53%), which does not require further purification;

[0143] The NMR characterization of compound 1 yielded the following results: 1 ¹H NMR (400MHz, chloroform) δ 6.76 (s, 1H), 4.77 (s, 1H), 3.55 (m, 2H), 3.506 (m, 2H), 1.42 (s, 9H);

[0144] Step S12: Add 2.7 g (8.29 mmol) of cesium carbonate and 50 mL of dry THF (tetrahydrofuran) to a 100 mL Schlenk flask; then add 1.27 g (6.85 mmol) of 1.39 g (6.85 mmol) of chloropentafluorobenzene (compound 2) and 0.88 g (5.47 mmol) of compound 1; purge the reaction mixture with Ar (gas) and stir overnight at 80 °C under Ar (g); then allow the reaction mixture to cool; filter the reaction mixture using suction; concentrate the organic phase under vacuum to obtain a crude product; purify by flash chromatography (PE-DCM, 1:1), and further purify by vacuum distillation to obtain a white solid compound 3, which requires no further purification;

[0145] Compound 3 was characterized by H NMR: 1 ¹H NMR (400MHz, chloroform) δ 4.98 (s, 1H), 4.20 (t, J = 5.0Hz, 2H), 3.45–3.43 (m, 2H), 1.38 (s, 9H);

[0146] Compound 3 was characterized by F NMR: 19 F NMR (400MHz, chloroform) δ -141.78 (d, J = 16.8, 2F), -155.8 (d, J = 16.8, 2F);

[0147] Step S13: 327 mg (1.0 mmol) of compound 3 was added to a 50 mL Schlenk flask. 25 mL of methanol and 0.45 g (2.0 mmol) of 57 wt% hydroiodic acid without stabilizer were added to this solution. The resulting solution was washed with Ar(g), and the reaction mixture was stirred at 50 °C for 1 hour under Ar(g) conditions. The reaction mixture was cooled to RT (Room Temperature), and 2 mol / L NaOH was added to bring it to alkalinity. The mixture was extracted three times with 20 mL of diethyl ether. The combined organic extract was dried over anhydrous Na₂SO₄, and the solvent was removed under reduced pressure to give organic compound M1.

[0148] The H NMR data of organic compound M1 in this embodiment are as follows: 1 H NMR (400MHz, DMSO-d6) δ4.19 (t, J = 5.6 Hz, 2H), 2.86 (t, J = 5.6 Hz, 2H), 1.64 (s, 2H).

[0149] The F NMR data of organic compound M1 in this embodiment are as follows: 19 F NMR(400MHz, DMSO-d6)δ(-143.25)-(-143.38)(m,2F),(-155.66)-(-155.69)(m,2F).

[0150] Organic compound Example 2

[0151] The synthetic route of organic compound M2 in this embodiment is as follows:

[0152]

[0153]

[0154] The synthesis of organic compound M2 in this embodiment is similar to that of organic compound M1 in Example 1. The difference is that in this embodiment, 1.39 g (6.85 mmol) of chloropentafluorobenzene in step S12 of Example 1 is replaced with 1.69 g (6.85 mmol) of bromopentafluorobenzene, while the reaction conditions remain unchanged.

[0155] The H NMR data for compound 3 in this embodiment are as follows: 1 H NMR (400MHz, Chloroform-d) δ5.0 (s, 1H), 4.25 (t, J = 5.0Hz, 2H), 3.49-3.48 (m, 2H), 1.43 (s, 9H).

[0156] The F NMR data for compound 3 in this embodiment are as follows: 19F NMR (400MHz, Chloroform-d) δ -134.02 (d, J = 23, 2F), -155.17 (d, J = 23, 2F).

[0157] The H NMR data of organic compound M2 in this embodiment are as follows: 1 H NMR (400MHz, DMSO-d6) δ4.19 (t, J = 5.6 Hz, 2H), 2.86 (t, J = 5.6 Hz, 2H), 1.59 (s, 2H).

[0158] The F NMR data for organic compound M2 in this embodiment are as follows: 19 F NMR(400MHz, DMSO-d6)δ(-135.06)-(-135.14)(m,2F),(-155.12)-(-155.19)(m,2F).

[0159] Organic compound Example 3

[0160] The synthetic route of organic compound M3 in this embodiment is as follows:

[0161]

[0162]

[0163] The synthesis of organic compound M3 in this embodiment is similar to that of organic compound M1 in Example 1. The difference is that in this embodiment, 1.39 g (6.85 mmol) of chloropentafluorobenzene in step S12 of Example 1 is replaced with 2.0 g (6.85 mmol) of pentafluoroiodobenzene, while the reaction conditions remain unchanged.

[0164] The H NMR data for compound 3 in this embodiment are as follows: 1 H NMR (400MHz, Chloroform-d) δ5.05 (s, 1H), 4.31 (t, J = 5.0Hz, 2H), 3.55-3.53 (m, 2H), 1.47 (s, 9H).

[0165] The F NMR data for compound 3 in this embodiment are as follows: 19 F NMR (400MHz, Chloroform-d) δ -122.57 (d, J = 23.0, 2F), -153.56 (d, J = 23.0, 2F).

[0166] The H NMR data of organic compound M3 in this embodiment are as follows: 1H NMR (400MHz, DMSO-d6) δ4.18 (t, J = 5.6 Hz, 2H), 2.87 (t, J = 5.6 Hz, 2H), 2.34 (s, 2H).

[0167] The F NMR data of organic compound M3 in this embodiment are as follows: 19 F NMR(400MHz, DMSO-d6)δ(-122.80)-(-122.84)(m,2F),(-153.90)-(-153.95)(m,2F).

[0168] Organic compound Example 4

[0169] The synthetic route of organic compound M6 in this embodiment is as follows:

[0170]

[0171]

[0172] The synthesis of organic compound M6 in this embodiment is similar to that of organic compound M1 in Example 1. The difference is that in this embodiment, ethanolamine in step S11 of Example 1 is replaced with DL-2-amino-3-methyl-1-butanol (CAS No.: 473-75-6) in this embodiment, while the reaction conditions remain unchanged.

[0173] The H NMR data of compound 1 in this embodiment are as follows: 1 H NMR (400MHz, DMSO-d6) δ0.88(d,6H),1.42(s,9H),2.22(m,1H),3.25-3.50(m,2H),3.40(m,1H),4.49(s,1H),7.67(s,1H).

[0174] The H NMR data for compound 3 in this embodiment are as follows: 1 H NMR (400MHz, DMSO-d6) δ0.88(d,6H),1.42(s,9H),2.22(m,1H),3.56-3.81(m,2H),7.67(s,1H).

[0175] The F NMR data for compound 3 in this embodiment are as follows: 19 F NMR(400MHz,Chloroform-d)δ-119.93(d,2F),-154.24(d,2F).

[0176] The H NMR data of organic compound M6 in this embodiment are as follows: 1H NMR (400MHz, DMSO-d6) δ0.88(d,6H),1.55(m,1H),1.7(s,2H),2.93(m,1H),3.56-3.81(m,2H).

[0177] The F NMR data for organic compound M6 in this embodiment are as follows: 19 F NMR(400MHz, DMSO-d6)δ(-120.22)-(-120.25)(m,2F),(-154.51)-(-154.53)(m,2F).

[0178] Organic compound Example 5

[0179] The synthetic route of organic compound M9 in this embodiment is as follows:

[0180]

[0181]

[0182] The synthesis of organic compound M9 in this embodiment is similar to that of organic compound M1 in Example 1. The difference is that in this embodiment, ethanolamine in step S11 of Example 1 is replaced with 2-amino-1-phenylethanol, while the reaction conditions remain unchanged.

[0183] The H NMR data of compound 1 in this embodiment are as follows: 1 H NMR (400MHz, DMSO-d6) δ1.42(s,9H),3.31-3.56(m,2H),5.54(m,1H),5.67(s,1H),6.76(s,1H),7.25(m,1H),7.34(d,2H),7.43(d,2H).

[0184] The H NMR data for compound 3 in this embodiment are as follows: 1 H NMR (400MHz, DMSO-d6) δ1.42(s,9H),3.54-3.79(m,2H),5.60(m,1H),6.76(s,1H),7.25(m,3H),7.32(m,2H).

[0185] The F NMR data for compound 3 in this embodiment are as follows: 19 F NMR(400MHz,Chloroform-d)δ-119.94(d,2F),-154.26(d,2F).

[0186] The H NMR data of organic compound M9 in this embodiment are as follows: 1H NMR (400MHz, DMSO-d6) δ1.6(s,2H),3.23-3.48(m,2H),4.93(m,1H),7.25(d,3H),7.32(d,2H).

[0187] The F NMR data for organic compound M9 in this embodiment are as follows: 19 F NMR(400MHz,DMSO-d6)δ(-120.27)-(-120.30)(m,2F),(-154.55)-(-154.57)(m,2F).

[0188] Organic compound Example 6

[0189] The synthetic route of organic compound M12 in this embodiment is as follows:

[0190]

[0191] The synthesis of organic compound M12 in this embodiment is similar to that of organic compound M1 in Example 1. The difference is that in this embodiment, ethanolamine in step S11 of Example 1 is replaced with 3-amino-1,2-propanediol, while the reaction conditions remain unchanged.

[0192] The H NMR data of compound 1 in this embodiment are as follows: 1 H NMR (400MHz, DMSO-d6) δ1.42(s,9H),3.04-3.29(m,2H),3.53-3.59(m,2H),4.22(m,1H),4.94(s,1H),5.37(s,1H),6.76(s,1H).

[0193] The H NMR data for compound 3 in this embodiment are as follows: 1 H NMR (400MHz, DMSO-d6) δ1.42(s,9H),3.04-3.29(m,2H),3.95-4.20(m,2H),4.72(m,1H),5.37(s,1H),6.76(s,1H).

[0194] The F NMR data for compound 3 in this embodiment are as follows: 19 F NMR(400MHz,Chloroform-d)δ-119.96(d,2F),-154.28(d,2F).

[0195] The H NMR data for the organic compound M12 in this embodiment are as follows: 1H NMR (400MHz, DMSO-d6) δ1.7(s,2H),2.65-2.90(m,2H),3.95-4.20(m,2H),4.05(m,1H),5.37(s,1H).

[0196] The F NMR data for the organic compound M12 in this embodiment are as follows: 19 F NMR(400MHz, DMSO-d6)δ(-120.32)-(-120.36)(m,2F),(-154.59)-(-154.64)(m,2F).

[0197] Organic compound comparative example 1

[0198] The synthetic route for the organic compound P1 in this comparative example is as follows:

[0199]

[0200] The synthesis of organic compound P3 in this comparative example is similar to that of organic compound M1 in Example 1. The difference is that in this comparative example, 1.39 g (6.85 mmol) of chloropentafluorobenzene in step S12 of Example 1 is replaced with 1.27 g (6.85 mmol) of 1,2,3,4,5,6-hexafluorobenzene, while the reaction conditions remain unchanged.

[0201] The H NMR data for compound 3 in this comparative example are as follows: 1 ¹H NMR (400MHz, chloroform) δ 5.04 (s, 1H), 4.23 (t, J = 5.0Hz, 2H), 3.52–3.50 (m, 2H), 1.47 (s, 9H).

[0202] The F NMR data for compound 3 in this comparative example are as follows: 19 F NMR (400MHz, chloroform) δ(-156.75)—(-156.81)(m,2F),(-162.73)-(-162.79)(m,1F),(-162.96)-(-163.07)(m,2F).

[0203] The H NMR data of organic compound P1 in this comparative example are as follows: 1 H NMR (400MHz, DMSO-d6) δ4.12 (t, J = 5.0 Hz, 2H), 2.85 (t, J = 5.0 Hz, 2H), 2.01 (s, 2H).

[0204] The F NMR data for organic compound P1 in this comparative example are as follows: 19F NMR(400MHz, DMSO-d6)δ(-156.52)-(-156.58)(m,2F),(-163.43)-(-163.55)(m,1F),(-164.02)-(-164.14)(m,2F).

[0205] Organic compound comparative example 2

[0206] The chemical structural formula of the organic compound P2 in this comparative example is as follows:

[0207]

[0208] Organic compound comparative example 3

[0209] The chemical structural formula of the organic compound P3 in this comparative example is as follows:

[0210]

[0211] Organic compound comparative example 4

[0212] The chemical structural formula of organic compound P4 in this comparative example is as follows:

[0213]

[0214] Organic compound comparative example 5

[0215] The chemical structural formula of organic compound P5 in this comparative example is as follows:

[0216]

[0217] Organic compound comparative example 6

[0218] The chemical structural formula of organic compound P6 in this comparative example is as follows:

[0219]

[0220] Example 1 of perovskite thin film

[0221] A composition is provided comprising a perovskite material precursor, organic compound M1 of Organic Compound Example 1, DMF, and DMSO, wherein the volume ratio of DMF to DMSO is 4:1, the perovskite material precursor comprises FAI (methylammonium lead iodide), MAI (methylammonium iodide), and PbI2 in a molar ratio of 0.8:0.2:1, and the molar ratio of organic compound M1 to the perovskite material precursor is 0.07:2.

[0222] The composition was spin-coated onto a silicon-based glass substrate at 5000 rpm for 60 seconds. When the spin coating was completed for 40 seconds, toluene, the anti-solvent, was added dropwise, and the mixture was heat-treated at 80°C for 10 minutes to obtain a perovskite film with a thickness of 43 nm.

[0223] Examples 2-6 of perovskite thin films

[0224] The perovskite thin film examples 2-6 are basically the same as those of the perovskite thin film example 1, except that the organic compounds in the organic compounds of ...

[0225] Example 7 of perovskite thin films

[0226] Example 7 of this perovskite thin film is basically the same as Example 1 of the perovskite thin film, except that the molar ratio of organic compound M1 to perovskite material precursor in this example is 0.05:2.

[0227] Perovskite Thin Film Example 8

[0228] Example 8 of this perovskite thin film is basically the same as Example 1 of the perovskite thin film, except that the molar ratio of organic compound M1 to perovskite material precursor in this example is 0.09:2.

[0229] Comparative Examples 1-6 of Perovskite Thin Films

[0230] The perovskite thin film comparative examples 1 to 6 are basically the same as those in perovskite thin film example 1, except that the organic compounds in organic compounds in organic compounds example 2 to 6 are replaced with the organic compounds in organic compounds example 1.

[0231] Perovskite thin film performance testing:

[0232] Fluorescence quantum yield (PLQY) tests were performed on the perovskite thin films of Examples 1-8 and Comparative Examples 1-6. The test results are shown in Table 1.

[0233] The fluorescence quantum yield (PLQY) test method is as follows: The PLQY of the perovskite thin film is measured using a fluorescence spectrometer. The perovskite thin film is placed on the sample stage of the spectrometer, the excitation light source and integrating sphere are turned on, the spectral sensitivity is calibrated, and the measurement can be started to obtain the emission spectrum of the perovskite thin film. The PLQY value of the perovskite thin film is calculated by the test software.

[0234] Table 1:

[0235]

[0236]

[0237] As shown in Table 1, compared with the perovskite film of Comparative Example 1, the perovskite films of Examples 1 to 8 have a PLQY of over 95%, which is due to the strong σ vacancies generated by the FI structure and the strong passivation effect brought by -NH2. Compared with FF, F-Br and F-Cl, the device examples of FI have excellent performance.

[0238] The poor PLQY of the perovskite films in Comparative Examples 2-6 is due to the presence of carbonyl bonds with high activity in the additives. Since the electronegativity of O in the C=O bond is greater than that of N in the amino group, it competes with O during perovskite passivation, preventing the amino group from functioning as a Lewis base and thus reducing film performance. Another reason for the low performance of the comparative films may be that the amino group in their materials is not monoamine (-NH2), significantly weakening its basicity and similarly leading to a decrease in PLQY.

[0239] Device Example 1

[0240] This embodiment of the device provides an optoelectronic device and its fabrication method, specifically including the following steps:

[0241] Using an indium tin oxide (ITO) anoly coated glass substrate as the anode, ultrasonic cleaning was performed with detergent, distilled water, acetone and isopropanol respectively. The cleaned substrate was then treated with ultraviolet ozone for 15 minutes to make its surface hydrophilic.

[0242] A PEDOT:PSS solution was spin-coated on the anode for 40 seconds at a speed of 4000 rpm and then heat-treated at 150°C for 15 minutes to obtain a hole injection layer with a thickness of 32 nm.

[0243] A TFB solution was spin-coated on the hole injection layer for 30 seconds at a speed of 3000 rpm, and then heat-treated at 150°C for 30 minutes to obtain a hole transport layer with a thickness of 35 nm.

[0244] A composition is provided comprising a perovskite material precursor, organic compound M1 of Organic Compound Example 1, DMF, and DMSO, wherein the volume ratio of DMF to DMSO is 4:1, the perovskite material precursor comprises FAI (methylammonium lead iodide), MAI (methylammonium iodide), and PbI2 in a molar ratio of 0.8:0.2:1, and the molar ratio of organic compound M1 to the perovskite material precursor is 0.07:2; the composition is spin-coated onto the hole transport layer at a rotation speed of 5000 rpm for 60 s, and toluene is added dropwise after 40 s of spin-coating, followed by heat treatment at 80°C for 10 minutes to obtain an active layer with a thickness of 43 nm;

[0245] Electron transport material TPBi was deposited on the active layer to obtain an electron transport layer with a thickness of 40 nm.

[0246] Electron injection material LiF is deposited on the electron transport layer to obtain an electron injection layer with a thickness of 1 nm.

[0247] Electrode material Al is deposited on the electron injection layer to obtain a cathode with a thickness of 120 nm;

[0248] Packaged, PeLED devices are obtained.

[0249] Device Examples 2-6

[0250] Device Examples 2-6 are basically the same as Device Example 1, except that Device Examples 2-6 use the organic compounds of Organic Compound Examples 2-6 to replace the organic compounds of Organic Compound Example 1.

[0251] Device Example 7

[0252] This device embodiment 7 is basically the same as device embodiment 1, except that the molar ratio of organic compound M1 to perovskite material precursor is 0.05:2 in this embodiment.

[0253] Device Example 8

[0254] This device embodiment 8 is basically the same as device embodiment 1, except that the molar ratio of organic compound M1 to perovskite material precursor is 0.09:2 in this embodiment.

[0255] Device Comparison Examples 1-6

[0256] The devices in Comparative Examples 1 to 6 are basically the same as those in Device Example 1, except that the devices in Comparative Examples 2 to 6 use the organic compounds of Comparative Examples 2 to 6 to replace the organic compounds in Organic Compound Example 1.

[0257] Device performance testing:

[0258] The maximum brightness L of the optoelectronic devices in Device Examples 1-8 and Device Comparative Examples 1-6 were tested respectively. max Tests included lifetime T95 test, lifetime T95@1000nit test, and photoelectric stability test. The test results are shown in Table 2.

[0259] Among them, the maximum brightness L maxThe testing method was as follows: Using a Fostar FPD optical property measurement device, an efficiency testing system was built by controlling a QE PRO spectrometer, Keithley 2400, and Keithley 6485 via LabVIEW. Parameters such as voltage, current, brightness, and emission spectrum were measured, and the maximum brightness L was recorded. max ;

[0260] The test methods for lifetime T95 and lifetime T95@1000nit are as follows: Under a constant current drive of 2mA, the time required for the brightness of the device to decrease to a certain percentage of its maximum brightness is defined as T95. This lifetime is the measured lifetime. To shorten the testing cycle, device lifetime testing is usually performed at high brightness by accelerating device aging, and the lifetime at high brightness is obtained by fitting the extended exponential decay brightness decay formula. For example, the lifetime at 1000nit is measured as T95@1000nit. The specific calculation formula is as follows:

[0261]

[0262] Among them, T95 L For longer lifespan at low brightness, T95 H For the measured lifetime under high brightness, L H To accelerate the device to its maximum brightness, L L The value is 1000 nits, and A is the acceleration factor. In this experiment, the lifetime of several groups of green QLED devices under rated brightness was measured, and the value of A was found to be 1.7.

[0263] The test method for photoelectric stability testing is as follows: the initial current efficiency of the prepared device is tested and recorded as CE0. Then, the device is placed in an environment with a temperature of 80℃ and a humidity of 50% and left to stand for 8 days. The current efficiency is tested again and recorded as CE1. The current efficiency fluctuation is calculated from the two measurements, i.e., CE% = (CE0-CE1) / CE0.

[0264] Table 2:

[0265]

[0266]

[0267] As shown in Table 2:

[0268] Compared to the optoelectronic device of Comparative Example 1, the optoelectronic devices of Examples 1 to 8 have higher brightness, longer lifespan and lower current efficiency fluctuations. This is due to the strong σ vacancies generated by adjacent F and X in the organic compounds in the active layer of Examples 1 to 8 and the strong passivation effect brought by -NH2.

[0269] As can be seen from device examples 1 to 3, the devices prepared by organic compounds with adjacent F and Br and organic compounds with adjacent F and Cl have superior performance.

[0270] Compared to the optoelectronic devices in Comparative Examples 2-6, the optoelectronic devices in Examples 1-8 exhibit higher brightness, longer lifespan, and lower current efficiency fluctuations. This may be because the organic compounds used in Comparative Examples 2-6 contain carbonyl bonds with high activity. Since the electronegativity of O in the C=O bond is greater than that of N in the amino group, it competes with the perovskite during passivation, preventing the amino group from functioning as a Lewis base and thus reducing the film performance. Furthermore, the amino groups in the organic compounds in Examples 3-6 are not monoamine (-NH2), significantly weakening their basicity and similarly resulting in a weaker amino group effect.

[0271] In summary, this application utilizes the aforementioned organic compounds, which possess both strong Lewis acids and Lewis bases, as amphoteric additives to prepare perovskite thin films, which significantly improves the performance and stabilizes the efficiency of perovskite light-emitting diode devices.

[0272] The technical solutions provided by the embodiments of this application have been described in detail above. Specific examples have been used to illustrate the principles and implementation methods of this application. The description of the above embodiments is only for the purpose of helping to understand the method and core ideas of this application. At the same time, for those skilled in the art, there will be changes in the specific implementation methods and application scope based on the ideas of this application. Therefore, the content of this specification should not be construed as a limitation of this application.

Claims

1. An organic compound, characterized in that, It has the structure shown in equation (I): X is selected from one of Cl, Br, and I; L is a linking group, selected from single bonds, unsubstituted or substituted C1-C bonds. 30 Alkylene, unsubstituted or substituted C1-C 30 alkenyl groups, unsubstituted or substituted C1-C 30 The ethynyl group, unsubstituted or substituted C1-C 30 One or more combinations of etheryl groups; wherein the substituted substituents include halogens, hydroxyl groups, silyl groups, C1-C1 groups. 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 One or more of the following: alkylthio, aryl with 6 to 60 ring atoms, aryloxy with 6 to 60 ring atoms, and arylthio with 6 to 60 ring atoms.

2. The organic compound according to claim 1, characterized in that, Includes one of the following features (1) to (5): (1) L is selected from single bonds, unsubstituted or substituted C1-C bonds. 20 Alkylene, unsubstituted or substituted C1-C 20 alkenyl groups, unsubstituted or substituted C1-C 20 The ethynyl group, unsubstituted or substituted C1-C 20 One or more combinations of etheryl groups, wherein the substituted substituents include halogens, hydroxyl groups, C1-C2 groups. 15 Alkyl, C1-C 15 Alkoxy, C1-C 15 One or more of the following: alkylthio, aryl with 6 to 30 ring atoms, aryloxy with 6 to 30 ring atoms, and arylthio with 6 to 30 ring atoms; (2) L is selected from single bonds, unsubstituted or substituted C1-C bonds. 15 Alkylene, unsubstituted or substituted C1-C 15 alkenyl groups, unsubstituted or substituted C1-C 15 The ethynyl group, unsubstituted or substituted C1-C 15 One or more combinations of etheryl groups, wherein the substituted substituents include halogens, hydroxyl groups, C1-C2 groups. 10 Alkyl, C1-C 10 Alkoxy, C1-C 10 One or more of the following: alkylthio, aryl with 6 to 20 ring atoms, aryloxy with 6 to 20 ring atoms, and arylthio with 6 to 20 ring atoms; (3) L is selected from single bonds, unsubstituted or substituted C1-C bonds. 15 Alkylene, unsubstituted or substituted C1-C 15 alkenyl groups, unsubstituted or substituted C1-C 15 One or more combinations of alkynyl groups, wherein the substituted substituents include halogens, hydroxyl groups, C1-C2 groups. 10 Alkyl, C1-C 10 Alkoxy, C1-C 10 One or more of the following: alkylthio, aryl with 6 to 20 ring atoms, aryloxy with 6 to 20 ring atoms, and arylthio with 6 to 20 ring atoms; (4) L is selected from single bonds, unsubstituted or substituted C1-C bonds. 15 Alkylene, wherein the substituted substituents include halogens, hydroxyl groups, C1-C2 groups. 10 Alkyl, C1-C 10 Alkoxy, C1-C 10 One or more of the following: alkylthio, aryl with 6 to 20 ring atoms, aryloxy with 6 to 20 ring atoms, and arylthio with 6 to 20 ring atoms; (5) L is selected from single bonds, unsubstituted or substituted C1-C bonds. 10 Alkylene, wherein the substituted substituents include hydroxyl, C1-C2, ... 10 One or more of alkyl groups and aryl groups having 6 to 20 cyclic atoms.

3. The organic compound according to claim 1, characterized in that, The organic compound has the structures shown in formulas (I-1) to (I-4):

4. The organic compound according to any one of claims 1 to 3, characterized in that, The organic compound is selected from any one of the compounds shown in formulas M1 to M12:

5. A composite material, characterized in that, Includes perovskite materials and the organic compounds described in any one of claims 1 to 4.

6. The composite material as described in claim 5, characterized in that, The organic compound is coordinated with the perovskite material; and / or In the composite material, the molar ratio of the organic compound to the perovskite material is (0.05–0.09):

1.

7. The composite material as described in claim 5, characterized in that, The perovskite material includes a metal halide perovskite material, and the chemical formula of the metal halide perovskite material is ABI a X’ b , where 0 < a ≤ 3, 0 ≤ b < 3, A is an organic amine cation or an inorganic cation, and the inorganic cation is Cs + , B is a metal cation, and the X' position is a halogen anion; Optionally, the organic amine cation is CH3NH 3+ CH3(CH2) n-2 NH3 + Or [NH3(CH2)] n NH3] 2+ , n≥2; Optionally, the metal cation is selected from Pb. 2+ ; Optionally, the halide anion is selected from one or more of chloride ions and bromide ions.

8. A composition, characterized in that, It includes perovskite material precursors, solvents, and organic compounds as described in any one of claims 1 to 4.

9. The composition according to claim 8, characterized in that, The perovskite material precursor includes YB1X1, YX2 and B2X3, wherein Y is an organic amine cation, B1 and B2 are each independently metal cations, and X1, X2 and X3 are each independently halide anions.

10. The composition according to claim 9, characterized in that, Includes at least one of the following features (1) to (6): (1) The organic amine cation is CH3NH 3+ CH3(CH2) n-2 NH3 + Or [NH3(CH2)] n NH3] 2+ , n≥2; (2) The metal cation is selected from Pb 2+ ; (3) The halide anion is selected from one or more of chloride ions and bromide ions; (4) The molar ratio of YB1X1, YX2, and B2X3 is (0.6~0.9):(0.1~0.4):1; (5) The molar ratio of the organic compound to the perovskite precursor is (0.05~0.09):2; (6) The solvent includes one or more of N,N-dimethylformamide, dimethyl sulfoxide, methanol, ethanol, isopropanol, 1-butanol, 1-pentanol, tetramethylethylenediamine, n-butyl acetate, dibutyl phthalate, and acetone.

11. A perovskite thin film, characterized in that, Includes the composite material described in any one of claims 5 to 7.

12. A method for preparing a perovskite thin film, characterized in that, Includes the following steps: Provide a composition according to any one of claims 8 to 10; The composition is deposited to obtain a wet film, and an antisolvent is added to the wet film to obtain a perovskite thin film.

13. The preparation method according to claim 12, characterized in that, Includes at least one of the following features (1) to (3): (1) The antisolvent includes one or more of toluene, dimethyl ethyl carbonate, ethyl acetate, and n-octane; (2) The volume ratio of the composition to the antisolvent is 1:(10-30); (3) After obtaining the wet film and before obtaining the perovskite thin film, a heat treatment is also included. Optionally, the temperature of the heat treatment is 75-85°C and the time of the heat treatment is 10-20 min.

14. An optoelectronic device, characterized in that, Includes the perovskite thin film according to claim 11, or includes the perovskite thin film prepared by the preparation method according to any one of claims 12 to 13.

15. The optoelectronic device as described in claim 14, characterized in that, The optoelectronic device includes an anode, an active layer, and a cathode stacked sequentially, wherein the active layer includes the perovskite thin film.

16. The optoelectronic device as described in claim 15, characterized in that, Includes at least one of the following features (1) to (4): (1) The thickness of the active layer is 35-45 nm; (2) The anode and the cathode each independently comprise a doped metal oxide electrode, a composite electrode, a graphene electrode, a carbon nanotube electrode, a metal element electrode, or an alloy electrode. The material of the doped metal oxide electrode includes 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, and cadmium-doped zinc oxide. The composite electrode includes AZO / Ag / AZO, AZO / Al / AZO, ITO / Ag / ITO, ITO / Al / ITO, and ZnO / Ag / ZnO. The materials of the elemental metal electrodes include one or more of Ag, Ni, Pt, Au, Ir, Cu, Mo, Al, Ca, Mg, and Ba, and the alloy electrodes include one or more of Au:Mg alloy electrodes and Ag:Mg alloy electrodes. (3) The optoelectronic device further includes an electron transport layer disposed between the active layer and the cathode. The material of the electron transport layer includes one or more of inorganic electron transport materials and organic electron transport materials. The inorganic electron transport material includes one or more of metal oxides, doped metal oxides, IIB-VIA group semiconductor materials, IIIA-VA group semiconductor materials, and IB-IIIA-VIA group semiconductor materials. The metal oxide includes one or more of ZnO, TiO2, SnO2, ZrO2, and Ta2O5. The metal oxide in the doped metal oxide includes ZnO, TiO2, SnO2, ZrO2, and Ta2O5.

5. One or more of Al2O3, wherein the dopant in the doped metal oxide includes one or more of Al, Mg, Li, Mn, Y, La, Cu, Ni, Zr, Ce, In, Ga, and Sn; the IIB-VIA group semiconductor material includes one or more of ZnS, ZnSe, and CdS; the IIIA-VA group semiconductor material includes one or more of InP and GaP; the IB-IIIA-VIA group semiconductor material includes one or more of CuInS and CuGaS; and the organic electron transport material includes one or more of quinoxaline compounds, imidazole compounds, triazine compounds, fluorene-containing compounds, and hydroxyquinoline compounds. (4) The optoelectronic device further includes a hole functional layer, which is disposed between the anode and the active layer. The hole functional layer includes one or both of a hole transport layer and a hole injection layer. Optionally, the hole transport layer material includes 4,4'-N,N'-dicarbazolyl-biphenyl, poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine], N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4”-diamine, N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine, poly(N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine), N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)spiro N,N'-bis(4-(N,N'-diphenyl-amino)phenyl)-N,N'-diphenylbenzidine, 4,4',4'-tris(N-carbazolyl)-triphenylamine, 4,4',4'-tris(N-3-methylphenyl-N-phenylamino)triphenylamine, poly[(9,9'-dioctylfluorene-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine))], poly(N-vinylcarbazole) and its derivatives, N,N'-bis(1-naphthyl)-N,N'-diphenyl-1,1'-biphenyl-4-4'-diamine, spiron NPB, poly (Phenylacetene), poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylenevinylene], poly[2-methoxy-5-(3',7'-dimethyloctyloxy)-1,4-phenylenevinylene], 2,2',7,7'-tetrakis[N,N-di(4-methoxyphenyl)amino]-9,9'-spirodifluorene, 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline], 1,3-di(carbazole-9-yl)benzene, polyaniline, polypyrrole, poly(p)phenylenevinylene, aromatic tertiary amines, polynuclear aromatic tertiary amines, 4,4 '-Bis(p-carbazolyl)-1,1'-biphenyl compounds, N,N,N',N'-tetraarylbenzidine, PEDOT:PSS and its derivatives, polymethacrylate and its derivatives, poly(9,9-octylfluorene) and its derivatives, poly(spirofluorene) and its derivatives, doped graphene, undoped graphene, C60, doped or undoped NiO, doped or undoped MoO3, doped or undoped WO3, doped or undoped V2O5, doped or undoped p-type gallium nitride, doped or undoped CrO3, doped or undoped CuO; Optionally, the material of the hole injection layer includes one or more of the following: 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzophenanthrene, PEDOT, PEDOT:PSS, PEDOT:PSS derivatives doped with s-MoO3, 4,4',4'-tris(N-3-methylphenyl-N-phenylamino)triphenylamine, tetracyanoquinone dimethyl ether, copper phthalocyanine, nickel oxide, molybdenum oxide, tungsten oxide, vanadium oxide, molybdenum sulfide, tungsten sulfide, and copper oxide.

17. A display device, characterized in that, Includes the optoelectronic device as described in any one of claims 14 to 16.

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