Organic matter and preparation method thereof, ink, thin film and photoelectric device

Abstract

The invention discloses an organic matter and a preparation method thereof, ink, a film and a photoelectric device, and relates to the technical field of display. The structural formula of the organic matter is as shown in formula (I). The organic matter provided by the invention has relatively high electron migration rate and the like.

Description

Technical Field

[0001] This application relates to the field of display technology, and in particular to an organic material and its preparation method, ink, thin film, and optoelectronic device. Background Technology

[0002] Currently, organic materials have poor electron transport properties and need further improvement. Summary of the Invention

[0003] In view of this, this application provides an organic compound and its preparation method, an ink, a thin film, and an optoelectronic device.

[0004] The embodiments of this application are implemented as follows: an organic compound, the structural formula of which is shown in formula (Ⅰ):

[0005]

[0006] Among them, H, D, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkyl mercapto, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C1-C30 alkylcarbonyl, substituted or unsubstituted C1-C30 alkoxycarbonyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C7-C30 aryloxy, substituted or unsubstituted arylamino with 6-60 ring atoms, substituted or unsubstituted aryl mercapto with 6-60 ring atoms, substituted or unsubstituted C5-C30 heteroaryl, substituted or unsubstituted C5-C30 heteroaryloxy, substituted or unsubstituted heteroarylamino with 5-60 ring atoms, and substituted or unsubstituted heteroaryl mercapto among one or more of the following:

[0007] Ar1 and Ar2 are each independently selected from H, D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkyl mercapto, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C1-C30 alkylcarbonyl, substituted or unsubstituted C1-C30 alkoxycarbonyl, or a ring with 6-60 substituted or unsubstituted atoms. One or more of the following: aryl, heteroaryl with 5 to 60 substituted or unsubstituted ring atoms, arylamino with 6 to 60 substituted or unsubstituted ring atoms, aryloxy with 6 to 60 substituted or unsubstituted ring atoms, arylthiol with 6 to 60 substituted or unsubstituted ring atoms, heteroarylamino with 5 to 60 substituted or unsubstituted ring atoms, heteroaryloxy with 5 to 60 substituted or unsubstituted ring atoms, and heteroarylthiol with 5 to 60 substituted or unsubstituted ring atoms;

[0008] When substituted, each substituent is independently selected from one or more of H, D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1-C30 alkyl, C1-C30 alkoxy, and aryl with 6-30 ring atoms;

[0009] The heteroatoms in the heteroaryl group, the heteroaryloxy group, the heteroarylamino group, and the heteroarylthiol group are each independently selected from one or more of O, P, N, and S.

[0010] Accordingly, embodiments of this application also provide a method for preparing an organic compound, comprising the following steps:

[0011] Compound a and a thiol compound are provided, mixed, and reacted to obtain compound b; wherein the structural formula of compound a is shown below:

[0012]

[0013] The structural formula of compound b is shown below:

[0014]

[0015] Heating compound b yields a first intermediate; an oxidant is provided, and the oxidant is mixed with the first intermediate to react and yield compound c, the structural formula of which is shown below:

[0016]

[0017] A first halide with the chemical formula R-X2 is provided. The first halide is mixed with compound c and reacted to obtain a second intermediate. A second halide with the chemical formula R is also provided. 12 -X3, the second halide is mixed with the second intermediate and reacted to obtain compound d, the structural formula of which is shown below:

[0018]

[0019] An aromatic compound is provided, the chemical formulas of the aromatic compound being H-Ar1 and H-Ar2. The aromatic compound is mixed with compound d and reacted to obtain an organic compound with the structural formula shown in formula (Ⅰ):

[0020]

[0021] Among them, X1, X2 and X3 are each independently selected from halogen groups;

[0022] m1 is selected from integers from 0 to 6; m2 is selected from integers from 0 to 6;

[0023] R is selected from one or more of H, D, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkyl mercapto, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C1-C30 alkyl carbonyl, substituted or unsubstituted C1-C30 alkoxy carbonyl, substituted or unsubstituted aryl with 6-60 ring atoms, substituted or unsubstituted aryloxy with 7-60 ring atoms, substituted or unsubstituted arylamino with 6-60 ring atoms, substituted or unsubstituted aryl mercapto with 6-60 ring atoms, substituted or unsubstituted heteroaryl with 5-60 ring atoms, substituted or unsubstituted heteroaryloxy with 5-60 ring atoms, substituted or unsubstituted heteroarylamino with 5-60 ring atoms, and substituted or unsubstituted heteroaryl mercapto with 5-60 ring atoms.

[0024] Ar1 and Ar2 are each independently selected from H, D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkyl mercapto, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C1-C30 alkylcarbonyl, substituted or unsubstituted C1-C30 alkoxycarbonyl, or a ring with 6-60 substituted or unsubstituted atoms. One or more of the following: aryl, heteroaryl with 5 to 60 substituted or unsubstituted ring atoms, arylamino with 6 to 60 substituted or unsubstituted ring atoms, aryloxy with 6 to 60 substituted or unsubstituted ring atoms, arylthiol with 6 to 60 substituted or unsubstituted ring atoms, heteroarylamino with 5 to 60 substituted or unsubstituted ring atoms, heteroaryloxy with 5 to 60 substituted or unsubstituted ring atoms, and heteroarylthiol with 5 to 60 substituted or unsubstituted ring atoms;

[0025] When substituted, each substituent is independently selected from one or more of H, D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1-C30 alkyl, C1-C30 alkoxy, and aryl with 6-30 ring atoms;

[0026] The heteroatoms in the heteroaryl group, the heteroaryloxy group, the heteroarylamino group, and the heteroarylthiol group are each independently selected from one or more of O, P, N, and S.

[0027] Accordingly, this application also provides an ink, which includes a solvent and the above-mentioned organic matter, or an organic matter prepared by the above-mentioned preparation method.

[0028] Accordingly, this application also provides a thin film, the material of which includes the above-mentioned organic matter or the organic matter prepared by the above-mentioned preparation method.

[0029] Accordingly, this application also provides an optoelectronic device, including an anode, a functional layer and a cathode stacked sequentially, wherein the material of the functional layer includes the above-mentioned organic matter, or an organic matter prepared by the above-mentioned preparation method. The organic matter provided in this application has high electron mobility, etc. Attached Figure Description

[0030] 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.

[0031] Figure 1 This is a flowchart of the method for preparing organic compounds provided in the embodiments of this application;

[0032] Figure 2 This is a schematic diagram of the structure of the optoelectronic device provided in the embodiments of this application.

[0033] Figure label:

[0034] Optoelectronic device 100; anode 10; hole injection layer 20; hole transport layer 30; light-emitting layer 40; electron transport layer 50; cathode 60. Detailed Implementation

[0035] 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.

[0036] 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 orientation shown 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.

[0037] 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.

[0038] In this application, "at least one" means one or more, and "more than one" means two or more. "One or more", "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.

[0039] 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.

[0040] In this application, aromatic groups, aromatic families, and aromatic ring systems have the same meaning and can be used interchangeably.

[0041] In this application, heteroaromatic groups, heteroaromatic families, and heteroaromatic ring systems have the same meaning and can be used interchangeably.

[0042] In this application, "substituted or unsubstituted" means that the defined group may or may not be substituted. It is understood that when the group is substituted by a substituent, the number of substituents may be one, two, three or more, and when the number of substituents is two or more, the substituents may be the same or different.

[0043] In this application, "ring atom number" refers to the number of ring atoms constituting the ring itself in a cyclic compound (e.g., a monocyclic or polycyclic compound) obtained by atomic bonding, i.e., the number of atoms forming the ring. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring atom count. The same applies to the "ring atom number" described below unless otherwise specified. For example, the benzene ring has 6 ring atoms, the naphthalene ring has 10 ring atoms, and the thiophene group has 5 ring atoms.

[0044] 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.

[0045] 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 60 ring atoms" refers to a heteroaryl group having 5 to 60 ring atoms, preferably a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl group having 5 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl group having 5 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, imidazole, 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.

[0046] 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 30, 1 to 25, 1 to 20, 1 to 15, 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 ...

[0047] 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."

[0048] 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), tert-butoxy (-OC(CH3)3 or -OtBu), and n-hexyloxy (-O-C6H). 13 ), n-Decaalkoxy (-OC) 10 H 21 ), n-dodecyloxy (-OC) 12 H 25 ).

[0049] "alkylthiol" refers to a group with the structure "-S-alkyl", that is, an alkyl group as defined above that is attached to other groups via a sulfur atom. Suitable examples of phrases containing this term include, but are not limited to: methylthio (-S-CH3 or -SMe), ethylthio (-S-CH2CH3 or -SEt), tert-butylthio (-SC(CH3)3 or -StBu), and n-hexanethio (-S-C6H). 13 ), n-Decadecylthio (-SC) 10 H 21 ), n-Dodecylthio (-SC) 12 H 25 Similarly, "aryl thiol" refers to a group with the structure "-S-aryl", and "heteroaryl thiol" refers to a group with the structure "-S-heteroaryl".

[0050] In this application, "aryloxy group" refers to a group with the structure "-O-aryl", that is, an aryl 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, phenoxy, naphthoxy, etc.

[0051] In this application, amino represents -NR 1 R 2 , where R 1 R 2 Each can independently represent H or alkyl, that is, amino can refer to -NH2, -NH (alkyl), or -N alkyl (alkyl).

[0052] In this application, "arylamino" refers to a group with the structure "-NR-aryl" or "-N-aryl (aryl)", that is, an aryl group as defined above is attached to other groups via an N atom, for example... "Heteroarylene amino" refers to a group with the structure "-NR-heteroaryl" or "-N-heteroaryl (heteroaryl)", that is, a heteroaryl group as defined above is attached to other groups via an N atom.

[0053] In this application, the asterisk (*) associated with a single bond indicates a linking site or fusion site. When no linking site is specified in the group, it indicates that any selectable linking site in the group is chosen as the linking site. For example, In this context, any connectable site on the two benzene rings and any connectable site on Z can serve as a connection site for connecting to the N atom in the main framework structure. It can be understood that when Z is a connectable site, Z is N. Alternatively, when Z is NR7, R7 can serve as a connection site.

[0054] In this application, the single bonds connecting the substituents extend through the corresponding ring, indicating that the substituent can be attached to any position on the ring. For example... R1 can be attached to any substituted site in the benzene ring. Furthermore, in this application, when the same substituent appears multiple times, it can be independently selected from different groups; if the above general formula can contain n1 R1s, then each R1 can be independently selected from different groups.

[0055] The terms “combinations thereof,” “any combination thereof,” and “any combination thereof” as used in this application include all suitable arrangements of any two or more of the listed items.

[0056] In this application, "halogen" represents -Cl, -Br, -F, or -I; hydroxyl represents -OH; carboxyl represents -COOH; nitro represents -NO2; sulfonic acid represents -SO3H; mercapto represents -SH; and cyano represents...

[0057] In this application, "alkyl carbonyl" refers to a structure with the following structure: The group, "alkoxycarbonyl", refers to the structure with The group is denoted by R. Where R represents an alkyl group, and C1 to C30 in the alkyl carbonyl group refers to the number of carbon atoms in the entire group.

[0058] In existing optoelectronic devices, inorganic materials are usually used as the electronic functional layer, which results in electron injection being much greater than hole injection. This causes an imbalance between electrons and holes in the light-emitting layer, affecting the luminous efficiency, stability, and lifespan of the optoelectronic device.

[0059] The technical solution of this application is as follows:

[0060] In a first aspect, embodiments of this application provide an organic compound, the structural formula of which is shown in formula (Ⅰ):

[0061]

[0062] Where m1 is selected from integers from 0 to 6; m2 is selected from integers from 0 to 6;

[0063] R is selected from one or more of H, D, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkyl mercapto, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C1-C30 alkyl carbonyl, substituted or unsubstituted C1-C30 alkoxy carbonyl, substituted or unsubstituted aryl with 6-60 ring atoms, substituted or unsubstituted aryloxy with 7-60 ring atoms, substituted or unsubstituted arylamino with 6-60 ring atoms, substituted or unsubstituted aryl mercapto with 6-60 ring atoms, substituted or unsubstituted heteroaryl with 5-60 ring atoms, substituted or unsubstituted heteroaryloxy with 5-60 ring atoms, substituted or unsubstituted heteroarylamino with 5-60 ring atoms, and substituted or unsubstituted heteroaryl mercapto with 5-60 ring atoms.

[0064] Ar1 and Ar2 are each independently selected from H, D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkyl mercapto, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C1-C30 alkylcarbonyl, substituted or unsubstituted C1-C30 alkoxycarbonyl, or a ring with 6-60 substituted or unsubstituted atoms. One or more of the following: aryl, heteroaryl with 5 to 60 substituted or unsubstituted ring atoms, arylamino with 6 to 60 substituted or unsubstituted ring atoms, aryloxy with 6 to 60 substituted or unsubstituted ring atoms, arylthiol with 6 to 60 substituted or unsubstituted ring atoms, heteroarylamino with 5 to 60 substituted or unsubstituted ring atoms, heteroaryloxy with 5 to 60 substituted or unsubstituted ring atoms, and heteroarylthiol with 5 to 60 substituted or unsubstituted ring atoms;

[0065] When substituted, each substituent is independently selected from one or more of H, D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1-C30 alkyl, C1-C30 alkoxy, and aryl with 6-30 ring atoms;

[0066] The heteroatoms in the heteroaryl group, the heteroaryloxy group, the heteroarylamino group, and the heteroarylthiol group are each independently selected from one or more of O, P, N, and S.

[0067] The organic compound provided in this application has two symmetrically arranged dibenzothiophene dioxide structures and a phenoxazine structure located between the two dibenzothiophene dioxide structures and sharing a benzene ring with them. The organic compound has a highly conjugated linear structure, which gives it good rigidity and can effectively adjust the LUMO energy level of the organic compound, thereby improving the electron transport efficiency of the organic compound.

[0068] In addition, by fine-tuning the compound structure, such as changing the type, number, and substitution sites of substituents Ar1 / Ar2 on the backbone structure, compounds with different electron mobilities can be obtained, providing a freer and broader selection for screening 100 film materials for optoelectronic devices.

[0069] In some embodiments, the C1-C30 alkyl group can be selected from C2-C28 alkyl, C5-C25 alkyl, C8-C20 alkyl, C10-C15 alkyl, C12-C15 alkyl, etc., specifically methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, pentadecyl, octadecyl, eicosyl, pentadecyl, etc.

[0070] In some embodiments, the C1-C30 alkoxy group can be selected from C2-C28 alkoxy, C5-C25 alkoxy, C8-C20 alkoxy, C10-C15 alkoxy, C12-C15 alkoxy, etc., specifically methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, nonoxy, decoxy, dodecoxy, pentadecoxy, octadecoxy, eicosoxy, pentadecoxy, etc.

[0071] In some embodiments, the C1-C30 alkyl mercapto group can be selected from C2-C28 alkyl mercapto group, C5-C25 alkyl mercapto group, C8-C20 alkyl mercapto group, C10-C15 alkyl mercapto group, C12-C15 alkyl mercapto group, etc., specifically methyl mercapto group, ethyl mercapto group, propyl mercapto group, butyl mercapto group, pentyl mercapto group, hexyl mercapto group, heptyl mercapto group, octyl mercapto group, nonyl mercapto group, decyl mercapto group, dodecyl mercapto group, pentadecyl mercapto group, octadecyl mercapto group, eicosyl mercapto group, pentadecyl mercapto group, etc.

[0072] In some embodiments, the C1-C30 alkyl carbonyl group can be selected from C2-C28 alkyl carbonyl, C5-C25 alkyl carbonyl, C8-C20 alkyl carbonyl, C10-C15 alkyl carbonyl, C12-C15 alkyl carbonyl, etc., specifically methyl carbonyl, ethyl carbonyl, propyl carbonyl, butyl carbonyl, pentyl carbonyl, hexyl carbonyl, heptyl carbonyl, octyl carbonyl, nonyl carbonyl, decyl carbonyl, dodecyl carbonyl, pentadecyl carbonyl, octadecyl carbonyl, eicosyl carbonyl, pentadecyl carbonyl, etc.

[0073] In some embodiments, the C1-C30 alkoxycarbonyl group can be selected from C2-C28 alkoxycarbonyl, C5-C25 alkoxycarbonyl, C8-C20 alkoxycarbonyl, C10-C15 alkoxycarbonyl, C12-C15 alkoxycarbonyl, etc., specifically methylcarbonyl, ethylcarbonyl, propylcarbonyl, butylcarbonyl, pentylcarbonyl, hexylcarbonyl, heptylcarbonyl, octylcarbonyl, nonylcarbonyl, decylcarbonyl, dodecyloxycarbonyl, pentadecyloxycarbonyl, octadecyloxycarbonyl, eicosyloxycarbonyl, pentadecyloxycarbonyl, etc.

[0074] In some embodiments, the aryl group having 6 to 60 ring atoms can be selected from aryl groups having 8 to 50 ring atoms, aryl groups having 10 to 40 ring atoms, aryl groups having 20 to 30 ring atoms, etc., specifically phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, etc.

[0075] In some embodiments, the heteroaryl group having 5 to 60 ring atoms can be selected from heteroaryl groups having 8 to 50 ring atoms, heteroaryl groups having 10 to 40 ring atoms, heteroaryl groups having 20 to 30 ring atoms, etc., specifically thiazolyl, thiophenel, furanyl, pyrrolel, pyridinyl, pyrimidinyl, imidazolyl, azole, pyrazinyl, indolyl, quinolinyl, pteridinyl, acridinel, etc.

[0076] In some embodiments, R is selected from hydrogen, deuterium, C1-C30 alkyl, C1-C30 alkyl mercapto, C1-C30 alkylamino, and C1-C20 alkoxy-substituted phenyl. In some embodiments, R is selected from C5-C20 alkyl and C5-C20 alkoxy-substituted phenyl.

[0077] m1 can be selected from 0, 1, 2, 3, 4, 5, 6. m2 can be selected from 0, 1, 2, 3, 4, 5, 6.

[0078] In some embodiments, m1 is selected from 0, that is, the organic compound does not have an Ar1 substituent in its structural formula; in other embodiments, m2 is selected from 0, that is, the organic compound does not have an Ar2 substituent in its structural formula.

[0079] In some embodiments, m1 and m2 are selected from 1, which can not only better enhance the electron-donating ability of organic compounds and improve their electron transport performance, but also make them easier to synthesize.

[0080] It is understandable that Ar1 and Ar2 can be the same or different.

[0081] In some embodiments, Ar1 and Ar2 are set to the same group, which makes the organic compound easier to synthesize.

[0082] In some embodiments, Ar1 and Ar2 are each independently selected from one of the following structures each time they appear:

[0083]

[0084] Where Z is -N, NR7, O, or S;

[0085] X is -N, NR8, -CR9, CR 10 R 11 S or O;

[0086] R1, R2, R3, R4, R5, and R6 are each independently selected from one or more of the following: substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkyl mercapto, and substituted or unsubstituted C1-C30 alkyl amino.

[0087] R8, R9, R 10 R 11 Each is independently selected from one or more of H, D, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkyl mercapto, substituted or unsubstituted C1-C30 alkylamino, and substituted or unsubstituted aryl with 6 to 30 ring atoms;

[0088] n1 and n2 are each independently selected from integers from 0 to 5;

[0089] n3 and n4 are each independently selected from integers from 0 to 4;

[0090] n5 and n6 are each independently selected from integers from 0 to 4;

[0091] When substituted, each substituent is independently selected from one or more of H, D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1-C30 alkyl, C1-C30 alkoxy, and aryl with 6-30 ring atoms.

[0092] In some embodiments, R1, R2, R3, R4, R5, and R6 are each independently selected from one or more of C1-C10 alkyl, C1-C10 alkoxy, C1-C10 alkyl mercapto, and C1-C10 alkylamino groups.

[0093] In some embodiments, R8, R9, R 10 R 11 Each is independently selected from one or more of H, D, C1-C10 alkyl, C1-C10 alkoxy, C1-C10 alkyl mercapto, C1-C10 alkylamino, phenyl, naphthyl, and biphenyl.

[0094] In some embodiments, n1 and n2 are each independently selected from 0 or 1.

[0095] In some embodiments, n3 and n4 are each independently selected from 0 or 1.

[0096] In some embodiments, n5 and n6 are each independently selected from 0 or 1.

[0097] In some embodiments, Ar1 and Ar2 are each independently selected from one of the following structures:

[0098]

[0099] In some embodiments, Ar1 and Ar2 are each independently selected from one of the following structural formulas (1-1) to (1-13):

[0100]

[0101] In some embodiments, the organic compound is selected from one of the following formulas M1 to M9:

[0102]

[0103]

[0104] Secondly, please refer to Figure 1 This application also provides a method for preparing an organic compound, wherein the synthetic route of the organic compound is as follows:

[0105]

[0106] The method for preparing the organic compound includes the following steps:

[0107] S11. Provide compound a and a thiol compound, mix them, and react them to obtain compound b; wherein, the structural formula of compound a is shown below:

[0108]

[0109] The structural formula of compound b is shown below:

[0110]

[0111] S12. Heating compound b yields a first intermediate; providing an oxidant, mixing the oxidant with the first intermediate, and reacting to yield compound c, the structural formula of which is shown below:

[0112]

[0113] S13. Provide a first halide, the first halide having the chemical formula R-X2; mix the first halide with compound c and react to obtain a second intermediate; provide a second halide, the second halide having the chemical formula R 12 -X3, the second halide is mixed with the second intermediate and reacted to obtain compound d, the structural formula of which is shown below:

[0114]

[0115] S14. Provide aromatic compounds, the chemical formulas of which are H-Ar1 and H-Ar2. Mix the aromatic compounds with compound d and react to obtain an organic compound with the structural formula shown in formula (Ⅰ):

[0116]

[0117] Among them, X1, X2 and X3 are each independently selected from halogen groups;

[0118] R is selected from one or more of H, D, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkyl mercapto, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C1-C30 alkyl carbonyl, substituted or unsubstituted C1-C30 alkoxy carbonyl, substituted or unsubstituted aryl with 6-60 ring atoms, substituted or unsubstituted aryloxy with 7-60 ring atoms, substituted or unsubstituted arylamino with 6-60 ring atoms, substituted or unsubstituted aryl mercapto with 6-60 ring atoms, substituted or unsubstituted heteroaryl with 5-60 ring atoms, substituted or unsubstituted heteroaryloxy with 5-60 ring atoms, substituted or unsubstituted heteroarylamino with 5-60 ring atoms, and substituted or unsubstituted heteroaryl mercapto with 5-60 ring atoms.

[0119] Ar1 and Ar2 are each independently selected from H, D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkyl mercapto, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C1-C30 alkylcarbonyl, substituted or unsubstituted C1-C30 alkoxycarbonyl, or a ring with 6-60 substituted or unsubstituted atoms. One or more of the following: aryl, heteroaryl with 5 to 60 substituted or unsubstituted ring atoms, arylamino with 6 to 60 substituted or unsubstituted ring atoms, aryloxy with 6 to 60 substituted or unsubstituted ring atoms, arylthiol with 6 to 60 substituted or unsubstituted ring atoms, heteroarylamino with 5 to 60 substituted or unsubstituted ring atoms, heteroaryloxy with 5 to 60 substituted or unsubstituted ring atoms, and heteroarylthiol with 5 to 60 substituted or unsubstituted ring atoms;

[0120] When substituted, each substituent is independently selected from one or more of H, D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1-C30 alkyl, C1-C30 alkoxy, and aryl with 6-30 ring atoms;

[0121] The heteroatoms in the heteroaryl group, the heteroaryloxy group, the heteroarylamino group, and the heteroarylthiol group are each independently selected from one or more of O, P, N, and S.

[0122] In some embodiments, X1, X2, and X3 are each independently selected from one of -F, -Cl, -Br, and -I.

[0123] In S11:

[0124] In some embodiments, the thiol compound includes one or more of 2-mercaptophenylboronic acid (CAS: 352526-00-2), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)benzenethiol (CAS: 1673542-05-6), and 2-boronbenzenethiol (CAS: 1450998-37-4). The thiol compound can undergo a Suzuki coupling reaction with compound a.

[0125] Specifically, the structural formula of the 2-mercaptophenylboronic acid is shown below:

[0126] The structural formula of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)benzenethiol is shown below:

[0127]

[0128] The structural formula of the 2-boronbenzylthiol is shown below:

[0129] In some embodiments, the molar ratio of compound a to the thiol compound is 1:(2-5), for example, 1:2.2, 1:2.5, 1:2.8, 1:3, 1:3.2, 1:3.5, 1:3.8, 1:4, 1:4.2, 1:4.5, 1:4.8, etc. Within the range of the molar ratio, the compound a and the thiol compound can undergo sufficient carbon-carbon coupling reaction.

[0130] In some embodiments, the mixing of compound a and the thiol compound further includes the addition of a first catalyst. The first catalyst can effectively improve the reaction efficiency of compound a and the thiol compound.

[0131] Further, the first catalyst comprises a palladium catalyst; the palladium catalyst comprises one or more of tetrakis(triphenylphosphine)palladium (Pd[P(C6H5)3]4), [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (Pd(dppf)Cl2), tridibenzylacetone dipalladium (Pd(dba)3), and 1,1'-bis(di-tert-butylphosphine)ferrocene palladium dichloroisocyanurate (Pd(dtbpf)Cl2).

[0132] The molar ratio of compound a to the first catalyst is 1:(0.1 to 0.2), for example, it can be 1:0.11, 1:0.12, 1:0.13, 1:0.14, 1:0.15, 1:0.16, 1:0.17, 1:0.18, 1:0.19, etc. Within the range of the molar ratio, it is beneficial for the first catalyst to increase the reaction rate.

[0133] In some embodiments, the mixing of compound a and the thiol compound further includes the addition of a first solvent to obtain a first mixture.

[0134] Further, the first solvent includes one or more of dichloromethane, dimethyl sulfoxide, toluene, chlorobenzene, diethylene glycol monobutyl ether, trimethoxybutanol, triethylene glycol monobutyl ether, diethylene glycol dimethyl ether, methanol, ethanol, propanol, butanol, ethylene glycol, isopropanol, glycerol, dimethyl sulfoxide, acetone, acetophenone, tetrahydrofuran, N,N-dimethylformamide, ethyl acetate, pyrrole, butyric acid, and cresol.

[0135] In some embodiments, the molar concentration of compound a in the first mixture is 0.0125 mmol / mL to 0.1 mmol / mL, for example, 0.02 mmol / mL, 0.03 mmol / mL, 0.04 mmol / mL, 0.05 mmol / mL, 0.06 mmol / mL, 0.07 mmol / mL, 0.08 mmol / mL, 0.09 mmol / mL, etc. Within this molar concentration range, it is beneficial for the full and uniform dispersion of compound a.

[0136] In some embodiments, the reaction between compound a and the thiol compound is carried out in an inert atmosphere.

[0137] In some embodiments, the reaction temperature between compound a and the thiol compound is 90°C to 120°C, for example, 92°C, 95°C, 98°C, 100°C, 102°C, 105°C, 108°C, 110°C, etc.; and the reaction time is 12h to 24h, for example, 15h, 18h, 20h, 22h, etc. Under the above reaction conditions, the yield of the reaction between compound a and the thiol compound is high.

[0138] In some embodiments, the reaction formula for the reaction between compound a and the thiol compound is shown below:

[0139]

[0140] In S12:

[0141] In some embodiments, heating the compound b further includes adding a second catalyst. The second catalyst can promote the reaction rate of the compound b under heating conditions.

[0142] Furthermore, the second catalyst includes one or more of palladium catalyst, nickel catalyst, and copper catalyst; the palladium catalyst includes palladium dichloride (PdCl2); the nickel catalyst includes nickel bromide (NiBr2); and the copper catalyst includes copper iodide (CuI).

[0143] The molar ratio of compound b to the second catalyst is 1:(0.1–0.2), for example, it can be 1:0.11, 1:0.12, 1:0.13, 1:0.14, 1:0.15, 1:0.16, 1:0.17, 1:0.18, 1:0.19, etc. Within the range of the stated molar ratio, it is beneficial for the second catalyst to increase the reaction rate.

[0144] In some embodiments, before heating the compound b, a second solvent is added to obtain a second mixture, and the second mixture is then heated.

[0145] Further, the second solvent includes one or more of dichloromethane, dimethyl sulfoxide, toluene, chlorobenzene, diethylene glycol monobutyl ether, trimethoxybutanol, triethylene glycol monobutyl ether, diethylene glycol dimethyl ether, methanol, ethanol, propanol, butanol, ethylene glycol, isopropanol, glycerol, dimethyl sulfoxide, acetone, acetophenone, tetrahydrofuran, N,N-dimethylformamide, ethyl acetate, pyrrole, butyric acid, and cresol.

[0146] In some embodiments, the molar concentration of compound b in the second mixture is 0.02 mmol / mL to 0.04 mmol / mL, for example, 0.022 mmol / mL, 0.025 mmol / mL, 0.028 mmol / mL, 0.03 mmol / mL, 0.032 mmol / mL, 0.035 mmol / mL, 0.038 mmol / mL, etc. Within this range of molar concentrations, it is beneficial for the full and uniform dispersion of compound b.

[0147] In some embodiments, the heating of compound b is carried out in an inert atmosphere.

[0148] In some embodiments, the temperature at which compound b is heated is 100°C to 150°C, for example, 105°C, 110°C, 115°C, 120°C, 125°C, 130°C, 135°C, 140°C, 145°C, etc.; the time is 12h to 24h, for example, 15h, 18h, 20h, 22h, etc. Under the above reaction conditions, compound b can undergo a complete ring-closing reaction to obtain the first intermediate.

[0149] Furthermore, the structural formula of the first intermediate is shown below:

[0150]

[0151] In some embodiments, the oxidant includes one or more of H2O2, NaClO, H5IO6, PhICl2, CrO3, KMnO4, KHSO5, and CH3CO3H.

[0152] In some embodiments, the oxidant has a mass fraction of 30% to 50%, for example, 32%, 35%, 38%, 40%, 42%, 45%, 48%, etc. Within this mass fraction range, it is beneficial for the oxidant to fully oxidize the first intermediate.

[0153] In some embodiments, the molar ratio of the first intermediate to the oxidant is 1:(40-80), for example, it can be 1:45, 1:50, 1:55, 1:60, 1:65, 1:70, 1:75, etc. Within the range of the molar ratio, it is beneficial for the first intermediate and the oxidant to undergo a sufficient redox reaction.

[0154] In some embodiments, the mixing of the first intermediate and the oxidant further includes the addition of a third solvent to obtain a third mixture.

[0155] Furthermore, the third solvent includes one or more of acetic acid, chloroform, toluene, acetic acid, dichloromethane, and ethyl acetate.

[0156] In some embodiments, the molar concentration of the first intermediate in the third mixture is 0.02 mmol / mL to 0.06 mmol / mL, for example, 0.025 mmol / mL, 0.03 mmol / mL, 0.035 mmol / mL, 0.04 mmol / mL, 0.045 mmol / mL, 0.05 mmol / mL, 0.055 mmol / mL, etc. Within this molar concentration range, it is beneficial for the first intermediate to be sufficiently and uniformly dispersed.

[0157] In some embodiments, the reaction temperature between the first intermediate and the oxidant is 40°C to 60°C, for example, 42°C, 45°C, 48°C, 50°C, 52°C, 55°C, 58°C, etc.; and the reaction time is 12h to 24h, for example, 15h, 18h, 20h, 22h, etc. Under the above reaction conditions, the yield of compound c formed by the reaction of the first intermediate and the oxidant is high.

[0158] It should be noted that the third solvent can also create ice bath conditions, where an oxidant is added and the temperature is then raised to the reaction temperature.

[0159] In some embodiments, the reaction formula for the yield of compound c from compound b is shown below:

[0160]

[0161] In S13:

[0162] The R group in the first halide is described above and will not be repeated here.

[0163] For example, the first halide includes one or more of 1-bromohexane (CAS: 111-25-1), 1-bromooctane (CAS: 111-83-1), 1-(hexoxy)-4-iodobenzene (CAS: 85557-94-4), p-decoxybromobenzene (CAS: 30752-20-6), and 1-bromododecane (CAS: 143-15-7).

[0164] In some embodiments, the mixing of the first halide with compound c further includes the addition of a first base. The first base can create an alkaline environment to promote the reaction between the first halide and compound c.

[0165] Furthermore, the first alkali includes one or more of KOH, LiOH, and NaOH.

[0166] The molar ratio of compound c to the first base is 1:(2-4), for example, it can be 1:2.2, 1:2.5, 1:2.6, 1:3, 1:3.2, 1:3.5, 1:3.8, etc. Within the range of the molar ratio, it is beneficial to increase the reaction rate between the first halide and compound c.

[0167] In some embodiments, the molar ratio of compound c to the first halide is 1:(1.5–3), for example, it can be 1:1.6, 1:1.7, 1:1.8, 1:1.9, 1:2, 1:2.1, 1:2.2, 1:2.3, 1:2.4, 1:2.5, 1:2.6, 1:2.7, 1:2.8, 1:2.9, etc. Within the range of the aforementioned molar ratio, it is beneficial for compound c and the first halide to react sufficiently to generate the second intermediate.

[0168] In some embodiments, the mixing of compound c and the first halide further includes the addition of a fourth solvent to obtain a fourth mixture.

[0169] Further, the fourth solvent includes one or more of the following: dichloromethane, dimethyl sulfoxide, toluene, chlorobenzene, diethylene glycol monobutyl ether, trimethoxybutanol, triethylene glycol monobutyl ether, diethylene glycol dimethyl ether, methanol, ethanol, propanol, butanol, ethylene glycol, isopropanol, glycerol, dimethyl sulfoxide, acetone, acetophenone, tetrahydrofuran, N,N-dimethylformamide, ethyl acetate, pyrrole, butyric acid, and cresol.

[0170] In some embodiments, the molar concentration of compound c in the fourth mixture is 0.01 mmol / mL to 0.06 mmol / mL, for example, 0.015 mmol / mL, 0.02 mmol / mL, 0.025 mmol / mL, 0.03 mmol / mL, 0.035 mmol / mL, 0.04 mmol / mL, 0.045 mmol / mL, 0.05 mmol / mL, 0.055 mmol / mL, etc. Within this molar concentration range, it is beneficial for the full and uniform dispersion of compound c.

[0171] In some embodiments, the reaction temperature between compound c and the first halide is 80°C to 110°C, for example, 85°C, 90°C, 95°C, 100°C, 105°C, etc.; the reaction time is 4h to 8h, for example, 4.5h, 5h, 5.5h, 6h, 6.5h, 7h, 7.5h, etc. Under these reaction conditions, the yield of the second intermediate formed by the reaction of compound c and the first halide is high.

[0172] In some embodiments, the structural formula of the second intermediate is shown below:

[0173]

[0174] It is understandable that the second halide primarily provides halogens, R 12 It can be any group conventional in the field.

[0175] In some embodiments, for example, the second halide includes one or more of N-bromosuccinimide (NBS), N-iodosuccinimide (NIS), N-chlorosuccinimide (NCS), and tribromopyridine humate (3-PyHBr3).

[0176] In some embodiments, the molar ratio of the second intermediate to the second halide is 1:(2-4), for example, 1:2.2, 1:2.5, 1:2.8, 1:3, 1:3.2, 1:3.5, 1:3.8, etc. Within the range of the molar ratio, it is beneficial for the compound c and the second halide to react fully, displacing the halogen in the second halide.

[0177] In some embodiments, the mixing of the second intermediate and the second halide further includes the addition of a fifth solvent to obtain a fifth mixture.

[0178] Further, the fifth solvent includes one or more of the following: dichloromethane, dimethyl sulfoxide, toluene, chlorobenzene, diethylene glycol monobutyl ether, trimethoxybutanol, triethylene glycol monobutyl ether, diethylene glycol dimethyl ether, methanol, ethanol, propanol, butanol, ethylene glycol, isopropanol, glycerol, dimethyl sulfoxide, acetone, acetophenone, tetrahydrofuran, N,N-dimethylformamide, ethyl acetate, pyrrole, butyric acid, and cresol.

[0179] In some embodiments, the molar concentration of the second intermediate in the fifth mixture is 0.01 mmol / mL to 0.06 mmol / mL, for example, 0.015 mmol / mL, 0.02 mmol / mL, 0.025 mmol / mL, 0.03 mmol / mL, 0.035 mmol / mL, 0.04 mmol / mL, 0.045 mmol / mL, 0.05 mmol / mL, 0.055 mmol / mL, etc. Within this molar concentration range, it is beneficial for the second intermediate to be sufficiently and uniformly dispersed.

[0180] In some embodiments, the reaction temperature between the second intermediate and the second halide is 0°C to 30°C, for example, 2°C, 5°C, 8°C, 10°C, 12°C, 15°C, 18°C, 20°C, 22°C, 25°C, 28°C, etc.; the reaction time is 0.5h to 4h, for example, 1h, 1.5h, 2h, 2.5h, 3h, 3.5h, etc. Under the aforementioned reaction conditions, the yield of compound d formed by the reaction of the second intermediate and the second halide is high.

[0181] In some embodiments, the reaction formula for the yield of compound d from compound c is shown below:

[0182]

[0183] In S14:

[0184] The Ar1 and Ar2 groups in the aromatic compounds are described above and will not be repeated here.

[0185] Exemplarily, the aromatic compounds include diphenylamine (CAS: 122-39-4), 2,2-dinaphthylamine (CAS: 532-18-3), 4-(dinaphthyl)-2-aminophenylboronic acid (CAS: 1232102-18-9), phenoxathia-2-boronic acid (CAS: 2304440-01-3), and 10-(4-boronic acid phenyl)-10H-phenoxazine (CAS: 1246021-62-4). One or more of the following: 4-(9H-carbazole-9-yl)phenylboronic acid (CAS: 419536-33-7), 4,4'-dimethoxy-4”-boronic triphenylamine (CAS: 201802-29-1), dibenzo[B,D]thiophene-3-ylboronic acid (CAS: 108847-24-1), and 10-(4-boronic phenyl)-10H-phenthiazine (CAS: 1246021-63-5).

[0186] In some embodiments, the molar ratio of compound d to the aromatic compound is 1:(3-5), for example, 1:3.2, 1:3.5, 1:3.8, 1:4, 1:4.2, 1:4.5, 1:4.8, etc. Within the range of the molar ratio, the compound d and the aromatic compound can undergo sufficient carbon-carbon coupling reaction.

[0187] In some embodiments, the mixing of compound d and the aromatic compound further includes the addition of a third catalyst. The third catalyst can effectively improve the reaction efficiency of compound d and the aromatic compound.

[0188] Further, the third catalyst includes a palladium catalyst; the palladium catalyst includes one or more of tetrakis(triphenylphosphine)palladium (Pd[P(C6H5)3]4), [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (Pd(dppf)Cl2), tridibenzylacetone dipalladium (Pd(dba)3), and 1,1'-bis(di-tert-butylphosphine)ferrocene palladium dichloroisocyanurate (Pd(dtbpf)Cl2).

[0189] The third catalyst may be the same as or different from the first catalyst.

[0190] The molar ratio of compound d to the third catalyst is 1:(0.1–0.2), for example, it can be 1:0.11, 1:0.12, 1:0.13, 1:0.14, 1:0.15, 1:0.16, 1:0.17, 1:0.18, 1:0.19, etc. Within the range of the above molar ratio, it is beneficial for the third catalyst to increase the reaction rate.

[0191] In some embodiments, the mixing of compound d and the aromatic compound further includes the addition of a second base. The second base can create an alkaline environment to promote the reaction between compound d and the aromatic compound.

[0192] Furthermore, the second base includes one or more of KOH, LiOH, and NaOH.

[0193] The molar ratio of compound d to the second base is 1:(2-4), for example, it can be 1:2.2, 1:2.5, 1:2.6, 1:3, 1:3.2, 1:3.5, 1:3.8, etc. Within the range of the molar ratio, it is beneficial to increase the reaction rate of compound d and the aromatic compound.

[0194] In some embodiments, the mixing of compound d and the aromatic compound further includes the addition of a sixth solvent to obtain a sixth mixture.

[0195] Further, the sixth solvent includes one or more of the following: dichloromethane, dimethyl sulfoxide, toluene, chlorobenzene, diethylene glycol monobutyl ether, trimethoxybutanol, triethylene glycol monobutyl ether, diethylene glycol dimethyl ether, methanol, ethanol, propanol, butanol, ethylene glycol, isopropanol, glycerol, dimethyl sulfoxide, acetone, acetophenone, tetrahydrofuran, N,N-dimethylformamide, ethyl acetate, pyrrole, butyric acid, and cresol.

[0196] In some embodiments, the molar concentration of compound d in the sixth mixture is 0.01 mmol / mL to 0.06 mmol / mL, for example, it can be 0.015 mmol / mL, 0.02 mmol / mL, 0.025 mmol / mL, 0.03 mmol / mL, 0.035 mmol / mL, 0.04 mmol / mL, 0.045 mmol / mL, 0.05 mmol / mL, 0.055 mmol / mL, etc. Within this molar concentration range, it is beneficial for the full and uniform dispersion of compound d.

[0197] In some embodiments, the reaction of compound d and the aromatic compound is carried out in an inert atmosphere.

[0198] In some embodiments, the reaction temperature between compound d and the aromatic compound is 90°C to 120°C, for example, 92°C, 95°C, 98°C, 100°C, 102°C, 105°C, 108°C, 110°C, etc.; and the reaction time is 12h to 24h, for example, 15h, 18h, 20h, 22h, etc. Under the above reaction conditions, the yield of the organic compound formed by the reaction of compound d and the aromatic compound is high.

[0199] In some embodiments, the reaction formula for the reaction between compound d and the aromatic compound is shown below:

[0200]

[0201] Thirdly, embodiments of this application also provide an ink, which includes a solvent and the aforementioned organic compound, or an organic compound prepared by the aforementioned preparation method.

[0202] In some embodiments, the solvent includes one or more of chlorobenzene, diethylene glycol monobutyl ether, trimethoxybutanol, triethylene glycol monobutyl ether, diethylene glycol dimethyl ether, methanol, ethanol, propanol, butanol, ethylene glycol, isopropanol, glycerol, dimethyl sulfoxide, acetone, acetophenone, tetrahydrofuran, N,N-dimethylformamide, ethyl acetate, pyrrole, butyric acid, and cresol.

[0203] In some embodiments, the mass concentration of the organic matter in the ink is 20 mg / mL to 50 mg / mL, for example, 25 mg / mL, 30 mg / mL, 35 mg / mL, 40 mg / mL, 45 mg / mL, etc. Within the range of mass concentration, the viscosity of the ink is suitable, which is beneficial for storage and film formation.

[0204] Fourthly, embodiments of this application also provide a thin film, the material of which includes the above-mentioned organic matter, or the organic matter prepared by the above-mentioned preparation method.

[0205] The film can be prepared from the above-mentioned ink using conventional techniques in the art.

[0206] Fifthly, please refer to Figure 2 This application also provides an optoelectronic device 100, which includes an anode 10, a functional layer and a cathode 60 stacked sequentially, wherein the material of the functional layer includes the above-mentioned organic material or the organic material prepared by the above-mentioned preparation method.

[0207] The optoelectronic device 100 provided in this application uses the aforementioned organic material as the material of the functional layer, which can effectively adjust the LUMO energy level of the functional layer, which is beneficial to electron transport, promotes the balance of electrons and holes, and thus improves the photoelectric efficiency and service life of the optoelectronic device 100.

[0208] In some embodiments, the anode 10 and the cathode 60 each independently comprise one or more of a metal, a carbon material, and a metal oxide; the metal comprises one or more of Al, Ag, Cu, Mo, Au, Ba, Ca, Yb, and Mg; the carbon material comprises one or more of graphite, carbon nanotubes, graphene, and carbon fibers; the metal oxide comprises a metal oxide electrode or a composite electrode in which a metal is disposed between doped or undoped transparent metal oxides, the material of the metal oxide electrode comprising one or more of ITO, FTO, ATO, AZO, GZO, IZO, MZO, MoO3, and AMO; the composite electrode comprises one or more of AZO / Ag / AZO, AZO / Al / AZO, ITO / Ag / ITO, ITO / Al / ITO, ZnO / Ag / ZnO, ZnO / Al / ZnO, ZnS / Ag / ZnS, ZnS / Al / ZnS, TiO2 / Ag / TiO2, and TiO2 / Al / TiO2. In this context, " / " indicates a stacked structure. For example, AZO / Ag / AZO represents a composite electrode consisting of sequentially stacked AZO, Ag, and AZO layers.

[0209] In some embodiments, the functional layer includes an electronic functional layer, and the material of the electronic functional layer includes the organic material.

[0210] The electronic functional layer includes one or more of the electron injection layer and the electron transport layer 50.

[0211] In some embodiments, the functional layer further includes a light-emitting layer 40, which is located between the anode and the electronic functional layer.

[0212] In some embodiments, the material of the light-emitting layer 40 includes one or more of organic light-emitting materials and quantum dot light-emitting materials.

[0213] The organic light-emitting material may be selected from, but is not limited to, one or more of the following: CBP:Ir(mppy)3(4,4'-bis(N-carbazole)-1,1'-biphenyl:tris[2-(p-tolyl)pyridinium(III)]), TCTX:Ir(mmpy)(4,4',4”-tris(carbazole-9-yl)triphenylamine:tris[2-(p-tolyl)pyridinium(III)]), diaromatic anthracene derivatives, stilbene aromatic derivatives, pyrene derivatives, fluorene derivatives, TBPe fluorescent materials, TTPX fluorescent materials, TBRb fluorescent materials, DBP fluorescent materials, delayed fluorescent materials, TTA materials, TADF (thermally activated delayed) materials, polymers containing BN covalent bonds, HLCT (hybrid local charge transfer excited state) materials, and Exciplex (excitoplex) light-emitting materials.

[0214] The quantum dot luminescent material may be selected from, but is not limited to, one or more of single-structure quantum dots, core-shell structure quantum dots, and perovskite semiconductor materials.

[0215] The materials for the single-structure quantum dots, the core material of the core-shell quantum dots, and the shell material of the core-shell quantum dots can be selected from, but are not limited to, one or more of group II-VI compounds, group IV-VI compounds, group III-V compounds, and group I-III-VI compounds. The shell of the core-shell quantum dots may include one or more layers. The group II-VI compounds may be selected from, but are not limited to, 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 IV-VI group compounds may be selected from, but are not limited to, one or more of SnS, SnSe, SnTe, PbS, PbSe, PbTe, SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, SnPbSSe, SnPbSeTe, and SnPbSTe. The group III-V compounds may be selected from, but are not limited to, 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 group I-III-VI compounds may be selected from, but are not limited to, one or more of CuInS2, CuInSe2, and AgInS2.

[0216] As an example, the core-shell structured quantum dots can be selected from, but are not limited to, one or more of CdSe / CdSeS / CdS, InP / ZnSeS / ZnS, CdZnSe / ZnSe / ZnS, CdSeS / ZnSeS / ZnS, CdSe / ZnS, CdSe / ZnSe / ZnS, ZnSe / ZnS, ZnSeTe / ZnS, CdSe / CdZnSeS / ZnS, and InP / ZnSe / ZnS. In the above descriptions of CdSe / ZnS, etc., the " / " indicates that the material after the " / " (as the shell) covers the material before the " / " (as the core).

[0217] The perovskite semiconductor material can be selected from, but is not limited to, doped or undoped inorganic perovskite semiconductors, or organic-inorganic hybrid perovskite semiconductors. The general structural formula of the inorganic perovskite semiconductor is AMX3, where A is Cs. + Ion, M is a divalent metal cation selected from Pb 2+ Sn 2+ Cu 2+ Ni 2+ Cd 2+ Cr 2+ Mn 2+ Co 2+ Fe 2+ 、Ge 2+ Yb 2+ Eu 2+ One or more of them, where X is a halide anion selected from Cl. - ,Br - I - One or more of the following. The general structural formula of the organic-inorganic hybrid perovskite semiconductor is BMX3, where B is an organic amine cation selected from CH3(CH2). n-2 NH3 + Or [NH3(CH2)] n NH3] 2+ Where n≥2, M is a divalent metal cation selected from Pb 2+ Sn 2+ Cu 2+ Ni 2+ Cd 2+ Cr 2+ Mn 2+ Co 2+ Fe 2+ 、Ge 2+ Yb 2+ Eu 2+ One or more of them, where X is a halide anion selected from Cl. - ,Br - I -One or more of them.

[0218] In some embodiments, the functional layer further includes a hole functional layer located between the anode 10 and the light-emitting layer 40.

[0219] The hole functional layer includes one or more of the hole injection layer 20 and the hole transport layer 30.

[0220] In some embodiments, the hole functional layer material includes 4,4'-N,N'-dicarbazolyl-biphenyl, 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, 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(carbazolyl-9-yl)triphenylamine, trichloroisocyanuric acid, and terbium-doped phosphate-based green. Color-emitting materials, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzphenanthrene, 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(4-butylphenyl-diphenylamine), poly[bis(4-phenyl)(4-butylphenyl)amine], polyaniline, polypyrrole, poly(p-)phenylenevinylene, poly(phenylenevinylene), poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylenevinylene], poly[2-methoxy-5-(3',7'-dimethyl) Octyloxy)-1,4-phenylenevinylene, copper phthalocyanine, aromatic tertiary amines, polynuclear aromatic tertiary amines, 4,4'-bis(p-carbazolyl)-1,1'-biphenyl compounds, N,N,N',N'-tetraarylbenzidine, PEDOT, PEDOT:PSS and its derivatives, PEDOT:PSS derivatives doped with s-MoO3, poly(N-vinylcarbazole) and its derivatives, polymethacrylate and its derivatives, poly(9,9-octylfluorene) and its derivatives, poly(spirofluorene) and its derivatives, N,N'-di(naphthyl-1-yl)-N,N'-diphenylbenzidine, spironolactone (NPB), nanocrystalline diamond, microcrystalline cellulose and tetracyanoquinone dimethane, doped graphene, undoped graphene, doped... The metal oxide particles are selected from one or more of the following: heterogeneous metal oxide particles, undoped metal oxide particles, metal sulfides, metal selenides, and metal nitrides. The metal oxides in the doped metal oxide particles and the metal oxides in the undoped metal oxide particles each independently include one or more of the following: MoO3, WO3, NiO, CrO3, CuO, and V2O5. The doping elements in the doped metal oxide particles include one or more of the following: Mo, W, Ni, Cr, Cu, and V. The metal sulfides include one or more of the following: CuS, MoS3, and WS3. The metal selenides include one or more of the following: MoSe3 and WSe3. The metal nitrides include p-type gallium nitride.

[0221] This application embodiment also provides a display device, which includes the above-described optoelectronic device 100.

[0222] 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.

[0223] 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.

[0224] Example 1

[0225] This embodiment provides an organic compound M1, the preparation process of which is shown in the following flowchart:

[0226]

[0227] The specific preparation method is as follows:

[0228] In a 100 mL two-necked flask, add compound M1-1: 3,7-dibromophenoxazine (2 mmol, 678 mg) (CAS: 832734-16-4), 3-mercaptophenylboronic acid (CAS: 352526-00-2) (5 mmol, 770 mg), the first catalyst Pd[P(C6H5)3]4 (0.2 mmol, 210 mg), and 40 mL of toluene. Purge with nitrogen and evacuate for 30 minutes using a vacuum pump. The mixture was stirred and heated to 110°C and reacted for 24 hours. The reaction was then stopped and cooled to room temperature. The reaction solution was extracted by repeatedly extracting with 200 mL of water and 1500 mL of dichloromethane 3 to 4 times. The resulting organic extract was dried with anhydrous magnesium sulfate, and the filtrate was collected and mixed with 200 to 300 mesh silica gel for column chromatography purification and separation. The mobile phase was petroleum ether: ethyl acetate (volume ratio 30:1). Finally, M1-2 was obtained as a white solid product with a yield of 70%.

[0229] M1-2 (1 mmol, 399 mg) was added to a 50 mL single-necked flask, followed by the second catalyst PdCl2 (0.1 mmol, 105 mg) and 40 mL of dimethyl sulfoxide. Nitrogen gas was introduced and the mixture was evacuated for 15 min using a vacuum pump. The mixture was stirred and heated to 140 °C for 12 h. The reaction was then stopped and cooled to room temperature. The reaction solution was extracted repeatedly with 200 mL of water and 1500 mL of dichloromethane 3 to 4 times. The resulting organic extract was dried with anhydrous magnesium sulfate and separated by column chromatography to obtain the first intermediate. The first intermediate was added to 10 mL of glacial acetic acid and 20 mL of CHCl3 solvent. 2.5 mL of 30% H2O2 aqueous solution was added under ice bath conditions. The temperature was raised to 60 °C and the reaction was carried out for 24 h. After the reaction was completed, the reaction solution was extracted and separated. The filtrate was separated by silica gel column chromatography with a mobile phase of petroleum ether:ethyl acetate (volume ratio 20:1) to finally obtain M1-3, which was light yellow in color and had a yield of 90%.

[0230] Add M1-3 (1 mmol, 459 mg), the first base KOH (2 mmol, 112 mg), and the first halide 1-bromohexane (2 mmol, 330 mg) (CAS: 111-25-1) to a 50 mL single-necked flask, dissolve in 10 mL of dimethyl sulfoxide, and stir at 60 °C for 3 h. Stop the reaction when the starting material has completely reacted. Distill the reaction solution under reduced pressure to remove the solvent. Separate the crude product by column chromatography using 200-300 mesh silica gel as the mobile phase. The second intermediate was obtained by reacting ether and ethyl acetate (volume ratio 20:1). The second intermediate was dissolved in 30 mL of dichloromethane, and then NBS (3 mmol, 540 mg) dissolved in 20 mL of dichloromethane was added dropwise at 0 °C. The reaction was stopped when the starting material had completely reacted. The reaction solution was distilled under reduced pressure to remove the solvent. The crude product was mixed with silica gel of 200 to 300 mesh and separated by column chromatography. The mobile phase was petroleum ether and ethyl acetate (volume ratio 20:1) to obtain M1-4 with a yield of 80%.

[0231] M1-4 (1 mmol, 699 mg) was added to a 100 mL double-necked flask, and the aromatic compound diphenylamine (3 mmol, 506 mg) (CAS: 122-39-4), the third catalyst Pd[P(C6H5)3]4 (0.1 mmol, 105 mg), and the second base KOH (2 mmol, 112 mg) were weighed and added. 40 mL of toluene was added, nitrogen gas was introduced and vacuum pump was used to evacuate for 15 min, the mixture was stirred and heated to 110 °C, and the reaction was continued for 24 h. The reaction was stopped and cooled to room temperature. The reaction solution was extracted by repeatedly extracting with 200 mL of water and 1500 mL of dichloromethane 3 to 4 times. The organic extract was dried with anhydrous magnesium sulfate, and the filtrate was collected and mixed with 200 to 300 mesh silica gel for column chromatography purification and separation. The eluent was petroleum ether, dichloromethane and ethyl acetate (volume ratio of 200:1:1) to obtain organic compound M1, which was a pale yellow solid with a yield of 72%.

[0232] Examples 2-9

[0233] Examples 2-9 are basically the same as Example 1, except that the organic compounds in Examples 2-9 are M2, M3, M4, M5, M6, M7, M8, and M9, respectively. The yields of the first halide and aromatic compounds, and M1-M9 are shown in Table 1.

[0234] Table 1

[0235]

[0236]

[0237]

[0238] The structural formulas of M1 to M9 can be found above. The molecular formulas of M1 to M9 and their performance under 500 MHz Chloroform-d conditions are also described. 1 The H NMR is as follows:

[0239] M1: δ8.03-7.99(m,2H),7.89-7.87(m,2H),7.74-7.72(m,2H),7.50-7.46(m,2H),7.28-7.23(m,8H),7.16-7.14(m,2H),7.10-7. 07(m,8H),7.06-7.02(m,4H),4.21(t,J=6.4Hz,2H),1.77-1.71(m,2H),1.47-1.41(m,2H),1.34-1.24(m,4H),0.91-0.88(m,3H);

[0240] M2:δ8.05-8.02(m,2H),7.88-7.86(m,2H),7.83-7.79(m,4H),7.77-7.73(m,6H),7.71-7.69(m,2H),7.50-7.43(m,10H),7.38-7.30(m,8H),7.16-7.13(m,4H),4.18(t,J=6.4Hz,2H),1.76-1.69(m,2H),1.48-1.42(m,2H),1.34-1.23(m,4H),0.92-0.87(m,3H);

[0241] M3:δ8.35-8.33(m,2H),8.27-8.24(m,2H),7.93-7.90(m,4H),7.88-7.81(m,8H),7.80(s,2H),7.69-7.66(m,2H),7.62-7.58(m,4H),7.58-7.57(m,2H),7.54-7.49(m,12H),7.17-7.11(m,8H),3.83(t,J=6.0Hz,2H),1.80-1.74(m,2H),1.39-1.26(m,10H),0.92-0.87(m,3H);

[0242] M4:δ8.34-8.32(m,2H),8.27-8.24(m,2H),7.99(s,2H),7.79-7.76(m,2H),7.67-7.62(m,4H),7.53(s,2H),7.24-7.11(m,8H),7.09-7.06(m,2H),7.03-7.00(m,2H),6.92-6.88(m,2H),4.02-3.99(m,2H),1.80-1.73(m,2H),1.49-1.42(m,2H),1.37-1.29(m,4H),0.91-0.87(m,3H);

[0243] M5:δ8.35-8.32(m,2H),8.28-8.24(m,2H),7.99(s,2H),7.70-7.62(m,6H),7.53(s,2H),7.34-7.28(m,4H),7.25-7.16(m,14H),6.96-6.87(m,6H),4.03-3.98(m,2H),1.80-1.73(m,2H),1.49-1.42(m,2H),1.37-1.28(m,4H),0.92-0.86(m,3H);

[0244] M6:δ8.36-8.33(m,2H),8.27-8.24(m,2H),8.12-8.09(m,4H),7.99(s,2H),7.71-7.65(m,10H),7.53(s,2H),7.47-7.43(m,4H),7.38-7.33(m,4H),7.31-7.26(m,4H),7.20-7.16(m,2H),6.92-6.88(m,2H),4.01(t,J=6.3Hz,2H),1.79-1.72(m,2H),1.47-1.41(m,2H),1.37-1.26(m,12H),0.92-0.87(m,3H);

[0245] M7:δ8.35-8.33(m,2H),8.28-8.24(m,2H),8.00-7.98(m,2H),7.69-7.66(m,2H),7.62-7.58(m,4H),7.53(s,2H),7.20-7.17(m,2H),7.16-7.13(m,4H),7.13-7.10(m,8H),6.95-6.91(m,8H),6.91-6.88(m,2H),4.01(t,J=6.3Hz,2H),3.78(s,12H),1.79-1.72(m,2H),1.48-1.40(m,2H),1.36-1.24(m,12H),0.93-0.87(m,3H);

[0246] M8:δ8.43-8.40(m,4H),8.32-8.30(m,2H),8.24-8.20(m,2H),8.10-8.06(m,4H),8.02-7.99(m,2H),7.91-7.87(m,4H),7.55-7.50(m,2H),7.29-7.25(m,2H),7.16-7.13(m,2H),4.22(t,J=6.3Hz,2H),1.75-1.68(m,2H),1.47-1.41(m,2H),1.33-1.22(m,16H),0.91-0.86(m,3H);

[0247] M9: δ8.17-8.15(m,2H),8.00-7.99(m,2H),7.95-7.92(m,2H),7.90-7.87(m,2H ),7.41-7.37(m,4H),7.31-7.28(m,4H),7.25-7.21(m,4H),7.20-7.16(m,4H), 7.15-7.14(m,2H),7.07-7.03(m,4H),7.00-6.97(m,4H),3.92(t,J=6.4Hz,2H) ,1.75-1.69(m,2H),1.47-1.41(m,2H),1.33-1.22(m,16H),0.91-0.86(m,3H).

[0248] Comparative Example 1

[0249] Comparative Example 1 provides an organic compound P1, the preparation reaction of which is as follows:

[0250]

[0251] Specifically, the preparation process includes:

[0252] Compound 1 (4 mmol, 1364 mg) (CAS: 832734-16-4) was added to a 100 mL two-necked flask, along with 3-mercaptophenylboronic acid (CAS: 352526-00-2) (5 mmol, 770 mg), Pd[P(C6H5)3]4 (0.1 mmol, 105 mg), and 40 mL of toluene. Nitrogen gas was introduced and the mixture was evacuated for 15 min. The mixture was stirred and heated to 110 °C for 24 h. The reaction was then stopped and cooled to room temperature. The reaction solution was extracted by repeatedly extracting with 200 mL of water and 1500 mL of dichloromethane 3 to 4 times. The resulting organic extract was dried with anhydrous magnesium sulfate, and the filtrate was collected and purified by column chromatography using 200 to 300 mesh silica gel. The mobile phase was petroleum ether:ethyl acetate (volume ratio 20:1). Compound 2 was finally obtained as a white solid product with a yield of 74%.

[0253] Compound 2 (1 mmol, 399 mg) was added to a 50 mL single-necked flask, followed by PdCl2 (0.1 mmol, 105 mg) and 40 mL of dimethyl sulfoxide. Nitrogen gas was introduced and the mixture was evacuated for 15 min using a vacuum pump. The mixture was stirred and heated to 140 °C for 12 h. The reaction was then stopped and cooled to room temperature. The reaction solution was extracted by repeatedly extracting with 200 mL of water and 1500 mL of dichloromethane 3 to 4 times. The resulting organic extract was dried with anhydrous magnesium sulfate. The crude product was mixed with 200 to 300 mesh silica gel and separated by column chromatography using petroleum ether:ethyl acetate (volume ratio 20:1). Compound M3 was finally obtained as a white solid with a yield of 95%.

[0254] Compound 3 (1 mmol, 395 mg) was added to a 50 mL single-necked flask, along with KOH (3 mmol, 168 mg) and 1-bromohexane (2 mmol, 330 mg) (CAS: 111-25-1). The solution was dissolved in 10 mL of dimethyl sulfoxide. The mixture was stirred at 60 °C for 3 h. The reaction was stopped once the starting material had completely reacted. The reaction solution was then distilled under reduced pressure to remove the solvent. The crude product was mixed with 200-300 mesh silica gel and separated by column chromatography using a mobile phase of petroleum ether:ethyl acetate. Ethyl ester (volume ratio 20:1) was used to obtain an intermediate product. The intermediate product was dissolved in 30 mL of dichloromethane, and then NBS (3 mmol, 540 mg) dissolved in 20 mL of dichloromethane was added dropwise at 0 °C. The reaction was stopped when the starting material had completely reacted. The reaction solution was distilled under reduced pressure to remove the solvent. The crude product was mixed with 200 to 300 mesh silica gel and separated by column chromatography. The mobile phase was petroleum ether:ethyl acetate (volume ratio 20:1), which is intermediate 4, with a yield of 80%.

[0255] Compound 4 (1 mmol, 635 mg) was added to a 100 mL double-necked flask, along with 3 mmol, 506 mg of diphenylamine (CAS: 122-39-4) and 0.1 mmol, 105 mg of Pd[P(C6H5)3]4. 40 mL of toluene was added, nitrogen gas was introduced, and a vacuum pump was used to evacuate the mixture for 15 min. The mixture was stirred and heated to 110 °C for 24 h. The reaction was then stopped and cooled to room temperature. The reaction solution was extracted using 200 mL of water and 1500 mL of dichloromethane, repeated 3 to 4 times. The resulting organic extract was dried over anhydrous magnesium sulfate, and the filtrate was collected and purified by column chromatography on 200-300 mesh silica gel. The eluent consisted of petroleum ether, dichloromethane, and ethyl acetate (volume ratio 200:1:1). The final product was organic compound P1, a pale yellow solid with a yield of 79%.

[0256] Organic P1 1H NMR (500MHz, Chloroform-d) is: δ8.03-8.01(m,2H),7.74-7.73(m,2H),7.70(s,2H),7.54(s,2H),7.27-7.23(m,10H),7.10-7. 08(m,8H),7.05-7.01(m,4H),4.21-4.18(m,2H),1.79-1.73(m,2H),1.47-1.41(m,2H),1.34-1.24(m,4H),0.91-0.88(m,3H).

[0257] Comparative Example 2

[0258] Comparative Example 2 provides an organic compound P2, whose structural formula is as follows:

[0259]

[0260] The preparation method is basically the same as that of Comparative Example 1, except that 1-bromohexane is replaced with 1-(hexoxy)-4-iodobenzene (CAS: 85557-94-4) and diphenylamine is replaced with phenoxathia-2-boronic acid (CAS: 2304440-01-3) to finally obtain organic compound P2.

[0261] Organic P2 1 H NMR (500MHz, Chloroform-d) is: δ8.84-8.81(m,2H),8.04-8.01(m,2H),7.83-7.7 7(m,4H),7.68-7.63(m,4H),7.38-7.33(m,2H),7.29-7.26(m,2H),7.19-7.16(m, 2H),7.13-7.08(m,2H),7.06-7.02(m,2H),6.99-6.89(m,6H),4.01(t,J=6.1Hz, 2H),1.79-1.73(m,2H),1.47-1.40(m,2H),1.36-1.27(m,4H),0.93-0.88(m,3H).

[0262] Comparative Example 3

[0263] Comparative Example 3 provides an organic compound P3: 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)phenyl TPBi (CAS: 192198-85-9), the structural formula of which is as follows:

[0264]

[0265] The electron mobility of the organic compounds in Examples 1-9 and Comparative Examples 1-3 was measured, and the results are shown in Table 2.

[0266] Electron mobility was measured using a conventional carrier mobility testing method. This method involved testing the current density-voltage curves of the optoelectronic devices (single-carrier transport thin-film devices, EODs) of Examples 1-9 and Comparative Examples 1-3. The EOD structure consisted of an anode / quantum dot emitting layer / electron transport layer / cathode. The electron transport layer was made of the organic materials used in Examples 1-9 and Comparative Examples 1-3, respectively, while the materials of other layers were the same as in Device Example 1. The space charge confinement current (SCLC) region in the current density-voltage curve was obtained, and then the value was calculated using the formula J = (9 / 8)ε. r ε0μ e V 2 / d 3 Calculate the electron mobility, where J represents the current density in mA / cm². -2 ;ε r ε₀ represents the relative permittivity, and μ represents the vacuum permittivity. e Electron mobility is expressed in cm. 2 V -1 s -1 V represents the driving voltage, with units of V; d represents the film thickness, with units of m.

[0267] Table 2

[0268]

[0269]

[0270] As shown in Table 2:

[0271] As can be seen from Examples 1-9 and Comparative Examples 1-3, the electron mobility of the organic compounds provided in Examples 1-9 is all above 6 × 10⁻⁶. -5 cm 2 V -1 s -1 The above-mentioned compounds exhibit high electron mobility, which can promote electron transport; in contrast, the electron mobility of the organic compound TPBi in Comparative Example 3 is only 3.3 × 10⁻⁶. -5 cm 2 V -1 s -1 The electron mobility of the organic compounds in Examples 1-9 is approximately half that of the organic compounds in Examples 1-9, indicating that the organic compounds provided in this application can significantly improve the electron mobility efficiency of organic materials. The organic compounds in Comparative Examples 1-2 have a dibenzothiophene structure, and their electron mobility is higher than that in Comparative Example 3, but still lower than that in Examples 1-9. This application has sulfonated the dibenzothiophene structure to give it a larger linear structure, which is very beneficial to promoting electron transport.

[0272] Device Example 1

[0273] This embodiment provides an optoelectronic device, the fabrication method of which is as follows:

[0274] Place the ITO glass slide in a glass dish containing an ethanol solution, and sonicate it with acetone, deionized water and ethanol for 20 minutes each in sequence, and then dry it with a nitrogen gun; then place the cleaned ITO glass slide in oxygen plasma for 10 minutes; and then treat the surface of the ITO substrate with ultraviolet-ozone for 15 minutes.

[0275] The cleaned ITO glass slides were spin-coated with PEDOT:PSS (25nm thick) in air at a speed of 5000r / min for 30s. After spin-coating, the slides were annealed in air at a temperature of 150℃ for 30min to obtain a hole injection layer with a thickness of 40nm.

[0276] TFB (8 mg / mL) was spin-coated onto the hole injection layer at a speed of 3000 r / min for 30 s. After spin-coating, the layer was annealed in a glove box at a temperature of 120 °C for 10 min to obtain the hole transport layer.

[0277] Quantum dots (QD) (20 mg / mL) were spin-coated onto the hole transport layer at a spin speed of 2000 r / min for 30 s; subsequently, they were coated with 10... -2 After standing for 15 minutes under MPa conditions, a light-emitting layer with a thickness of 30 nm was obtained.

[0278] The organic compound M1 from Example 1 was dissolved in ethanol (30 mg / mL) and spin-coated onto the luminescent layer at 3000 r / min for 30 s, followed by 10 -2 After standing for 15 minutes under MPa conditions, a 40nm electron transport layer was obtained.

[0279] Through thermal evaporation, the vacuum level is no higher than 3×10⁻⁶. -4 Pa, Ag is vapor-deposited at a rate of 1 angstrom / second for 200 s to form a top silver electrode with a thickness of 20 nm on the electron transport layer, and then encapsulated with epoxy resin to obtain an optoelectronic device.

[0280] Device Examples 2-9

[0281] Device Examples 2-9 are basically the same as Device Example 1, except that in Device Examples 2-9, organic compound M1 is replaced with M2, M3, M4, M5, M6, M7, M8 and M9 respectively.

[0282] Device Comparison Examples 1-3

[0283] The devices in Comparative Examples 1 to 3 are basically the same as those in Device Example 1, except that organic compound M1 is replaced with P1, P2 and P3 respectively in Comparative Examples 1 to 3.

[0284] The maximum luminance L of the measuring devices in Examples 1-9 and Comparative Examples 1-3 was measured. max Lifespan of T95 and T95@1000nit, and maximum current efficiency CE max .

[0285] Among them, the maximum brightness L max and maximum current efficiency CE max The testing method is 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 current efficiency CE was calculated. max ;

[0286] The test methods for lifetimes T95 and T95@1000nit are as follows: Under constant current or voltage drive, the time required for the device's brightness 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:

[0287]

[0288] 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 QLED devices under rated brightness was measured, and the value of A was found to be 1.7.

[0289] Table 3

[0290]

[0291] As shown in Table 3:

[0292] Based on Device Examples 1-9 and Comparative Examples 1-3, it can be seen that the brightness, lifespan, and current efficiency of the optoelectronic devices in Device Examples 1-9 are significantly higher than those in Comparative Examples 1-3. The maximum brightness of Device Examples 1-9 is 120,000 cd / m². 2 All of the above have a T95 of over 8 hours, a T95@1000nit of over 29000 hours, and a maximum current efficiency exceeding 170 cd / A, demonstrating high photoelectric performance. This indicates that using the organic material provided in this application as the electron transport layer material is beneficial for electron transport, promotes the balance between holes and electrons, thereby increasing the maximum brightness of the photoelectric device, extending its service life, and improving its maximum current efficiency, effectively improving the performance of the photoelectric device. In Comparative Example 3, the conventional electron transport material TPBi is used, and the performance of its photoelectric device is worse than that of the photoelectric devices in Comparative Examples 1 and 2 that use organic materials P1 and P2 as electron transport materials. Furthermore, P1 and P2 in Comparative Examples 1 and 2 both contain dibenzothiophene structures, which have not undergone sulfonation to obtain an O=S=O structure, resulting in performance inferior to M1 to M9 provided in this application.

[0293] The organic materials and their preparation methods, inks, thin films, and optoelectronic devices provided in 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 descriptions of the above embodiments are only for the purpose of helping to understand the methods 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, The structural formula of the organic compound is shown in formula (Ⅰ): Where m1 is selected from integers from 0 to 6; m2 is selected from integers from 0 to 6; R is selected from one or more of H, D, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkyl mercapto, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C1-C30 alkyl carbonyl, substituted or unsubstituted C1-C30 alkoxy carbonyl, substituted or unsubstituted aryl with 6-60 ring atoms, substituted or unsubstituted aryloxy with 7-60 ring atoms, substituted or unsubstituted arylamino with 6-60 ring atoms, substituted or unsubstituted aryl mercapto with 6-60 ring atoms, substituted or unsubstituted heteroaryl with 5-60 ring atoms, substituted or unsubstituted heteroaryloxy with 5-60 ring atoms, substituted or unsubstituted heteroarylamino with 5-60 ring atoms, and substituted or unsubstituted heteroaryl mercapto with 5-60 ring atoms. Ar1 and Ar2 are each independently selected from H, D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkyl mercapto, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C1-C30 alkylcarbonyl, substituted or unsubstituted C1-C30 alkoxycarbonyl, or a ring with 6-60 substituted or unsubstituted atoms. One or more of the following: aryl, heteroaryl with 5 to 60 substituted or unsubstituted ring atoms, arylamino with 6 to 60 substituted or unsubstituted ring atoms, aryloxy with 6 to 60 substituted or unsubstituted ring atoms, arylthiol with 6 to 60 substituted or unsubstituted ring atoms, heteroarylamino with 5 to 60 substituted or unsubstituted ring atoms, heteroaryloxy with 5 to 60 substituted or unsubstituted ring atoms, and heteroarylthiol with 5 to 60 substituted or unsubstituted ring atoms; When substituted, each substituent is independently selected from one or more of H, D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1-C30 alkyl, C1-C30 alkoxy, and aryl with 6-30 ring atoms; The heteroatoms in the heteroaryl group, the heteroaryloxy group, the heteroarylamino group, and the heteroarylthiol group are each independently selected from one or more of O, P, N, and S.

2. The organic compound as described in claim 1, characterized in that, R is selected from one of hydrogen, deuterium, C1-C30 alkyl, C1-C30 alkylthiol, C1-C30 alkylamino, and C1-C20 alkoxy-substituted phenyl groups; and / or Each time Ar1 and Ar2 appear, they are each independently selected from one of the following structures: Where Z is -N, NR7, O, or S; X is -N, NR8, -CR9, CR 10 R 11 S or O; R1, R2, R3, R4, R5, and R6 are each independently selected from one or more of the following: substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkyl mercapto, and substituted or unsubstituted C1-C30 alkyl amino. R8, R9, R 10 R 11 Each is independently selected from one or more of H, D, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkyl mercapto, substituted or unsubstituted C1-C30 alkylamino, and substituted or unsubstituted aryl with 6 to 30 ring atoms; n1 and n2 are each independently selected from integers from 0 to 5; n3 and n4 are each independently selected from integers from 0 to 4; n5 and n6 are each independently selected from integers from 0 to 4; When substituted, each substituent is independently selected from one or more of H, D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1-C30 alkyl, C1-C30 alkoxy, and aryl with 6-30 ring atoms.

3. The organic compound as described in claim 2, characterized in that, R is selected from one of C5-C20 alkyl or C5-C20 alkoxy-substituted phenyl groups; and / or R1, R2, R3, R4, R5, and R6 are each independently selected from one or more of C1-C10 alkyl, C1-C10 alkoxy, C1-C10 alkyl mercapto, and C1-C10 alkylamino groups; and / or, R8, R9, R 10 R 11 Each is independently selected from one or more of H, D, C1-C10 alkyl, C1-C10 alkoxy, C1-C10 alkyl mercapto, C1-C10 alkylamino, phenyl, naphthyl, and biphenyl; and / or, n1 and n2 are each independently selected from 0 or 1; and / or n3 and n4 are each independently selected from 0 or 1; and / or n5 and n6 are each independently selected from 0 or 1.

4. The organic compound according to any one of claims 1 to 3, characterized in that, Ar1 and Ar2 are each independently selected from one of the following structures:

5. The organic compound according to any one of claims 1 to 3, characterized in that, Ar1 and Ar2 are each independently selected from one of the following structural formulas (1-1) to (1-13): m1 is selected from 0 or 1; and / or m2 is selected from 0 or 1; and / or Ar1 and Ar2 are the same.

6. The organic compound as described in claim 1, characterized in that, The organic compound is selected from one of the following structures: M1 to M9:

7. A method for preparing an organic compound, characterized in that, Includes the following steps: Compound a and a thiol compound are provided, mixed, and reacted to obtain compound b; wherein the structural formula of compound a is shown below: The structural formula of compound b is shown below: Heating compound b yields a first intermediate; an oxidant is provided, and the oxidant is mixed with the first intermediate to react and yield compound c, the structural formula of which is shown below: A first halide with the chemical formula R-X2 is provided. The first halide is mixed with compound c and reacted to obtain a second intermediate. A second halide with the chemical formula R is also provided. 12 -X3, the second halide is mixed with the second intermediate and reacted to obtain compound d, the structural formula of which is shown below: An aromatic compound is provided, the chemical formulas of the aromatic compound being H-Ar1 and H-Ar2. The aromatic compound is mixed with compound d and reacted to obtain an organic compound with the structural formula shown in formula (Ⅰ): Among them, X1, X2 and X3 are each independently selected from halogen groups; m1 is selected from integers from 0 to 6; m2 is selected from integers from 0 to 6; R is selected from one or more of H, D, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkyl mercapto, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C1-C30 alkyl carbonyl, substituted or unsubstituted C1-C30 alkoxy carbonyl, substituted or unsubstituted aryl with 6-60 ring atoms, substituted or unsubstituted aryloxy with 7-60 ring atoms, substituted or unsubstituted arylamino with 6-60 ring atoms, substituted or unsubstituted aryl mercapto with 6-60 ring atoms, substituted or unsubstituted heteroaryl with 5-60 ring atoms, substituted or unsubstituted heteroaryloxy with 5-60 ring atoms, substituted or unsubstituted heteroarylamino with 5-60 ring atoms, and substituted or unsubstituted heteroaryl mercapto with 5-60 ring atoms. Ar1 and Ar2 are each independently selected from H, D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkyl mercapto, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C1-C30 alkylcarbonyl, substituted or unsubstituted C1-C30 alkoxycarbonyl, or a ring with 6-60 substituted or unsubstituted atoms. One or more of the following: aryl, heteroaryl with 5 to 60 substituted or unsubstituted ring atoms, arylamino with 6 to 60 substituted or unsubstituted ring atoms, aryloxy with 6 to 60 substituted or unsubstituted ring atoms, arylthiol with 6 to 60 substituted or unsubstituted ring atoms, heteroarylamino with 5 to 60 substituted or unsubstituted ring atoms, heteroaryloxy with 5 to 60 substituted or unsubstituted ring atoms, and heteroarylthiol with 5 to 60 substituted or unsubstituted ring atoms; When substituted, each substituent is independently selected from one or more of H, D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, cyano, C1-C30 alkyl, C1-C30 alkoxy, and aryl with 6-30 ring atoms; The heteroatoms in the heteroaryl group, the heteroaryloxy group, the heteroarylamino group, and the heteroarylthiol group are each independently selected from one or more of O, P, N, and S.

8. The preparation method according to claim 7, characterized in that, include: X1, X2, and X3 are each independently selected from one of -F, -Cl, -Br, and -I; and / or The thiol compounds include one or more of 2-mercaptophenylboronic acid, 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)phenylthiol, and 2-boronphenylthiol; and / or The oxidizing agent includes one or more of H2O2, NaClO, H5IO6, PhICl2, CrO3, KMnO4, KHSO5, and CH3CO3H; and / or The first halide includes one or more of 1-bromohexane, 1-bromooctane, 1-(hexoxy)-4-iodobenzene, p-decoxybromobenzene, and 1-bromododecane; and / or The second halide includes one or more of N-bromosuccinimide, N-iodosuccinimide, N-chlorosuccinimide, and tribromopyridine salts; and / or The aromatic compound comprises one or more of diphenylamine, 2,2-dinaphthylamine, 4-(dinaphthyl)2-aminophenylboronic acid, phenoxathia-2-boronic acid, 10-(4-boronicophenyl)-10H-phenoxazine, 4-(9H-carbazole-9-yl)phenylboronic acid, 4,4'-dimethoxy-4”-boronic acid triphenylamine, dibenzo[B,D]thiophene-3-ylboronic acid, and 10-(4-boronicophenyl)-10H-phenthiazine; and / or The structural formula of the first intermediate is shown below: and / or The structural formula of the second intermediate is shown below: and / or The oxidant has a mass fraction of 30% to 50%; and / or The molar ratio of compound a to the thiol compound is 1:(2-5); and / or The molar ratio of the first intermediate to the oxidant is 1:(40-80); and / or The molar ratio of compound c to the first halide is 1:(1.5–3); and / or The molar ratio of the second intermediate to the second halide is 1:(2-4); and / or The molar ratio of compound d to the aromatic compound is 1:(3-5); and / or The reaction temperature of compound a and the thiol compound is 90°C to 120°C; the reaction time is 12h to 24h; and / or The compound b is heated at a temperature of 100°C to 150°C for 12 hours to 24 hours; and / or The reaction temperature of the first intermediate and the oxidant is 40°C to 60°C; the reaction time is 12h to 24h; and / or The reaction of compound c and the first halide is carried out at a temperature of 80°C to 110°C for a time of 4 to 8 hours; and / or The reaction temperature of the second intermediate and the second halide is 0℃~30℃; the time is 0.5h~4h; and / or The reaction temperature of compound d and the aromatic compound is 90℃~120℃; the reaction time is 12h~24h.

9. An ink, characterized in that, The ink includes a solvent and an organic compound as described in any one of claims 1 to 6, or an organic compound prepared by the preparation method described in any one of claims 7 to 8.

10. A thin film, characterized in that, The material of the film includes the organic compound as described in any one of claims 1 to 6, or the organic compound prepared by the preparation method as described in any one of claims 7 to 8.

11. An optoelectronic device, characterized in that, It includes an anode, a functional layer, and a cathode stacked sequentially, wherein the material of the functional layer includes an organic compound as described in any one of claims 1 to 6, or an organic compound prepared by the preparation method as described in any one of claims 7 to 8.

12. The optoelectronic device as described in claim 11, characterized in that, The anode and the cathode each independently comprise one or more of a metal, a carbon material, and a metal oxide; the metal comprises one or more of Al, Ag, Cu, Mo, Au, Ba, Ca, Yb, and Mg; the carbon material comprises one or more of graphite, carbon nanotubes, graphene, and carbon fibers; the metal oxide comprises a metal oxide electrode or a composite electrode in which a metal is disposed between doped or undoped transparent metal oxides; the material of the metal oxide electrode comprises one or more of ITO, FTO, ATO, AZO, GZO, IZO, MZO, MoO3, and AMO; the composite electrode comprises one or more of AZO / Ag / AZO, AZO / Al / AZO, ITO / Ag / ITO, ITO / Al / ITO, ZnO / Ag / ZnO, ZnO / Al / ZnO, ZnS / Ag / ZnS, ZnS / Al / ZnS, TiO2 / Ag / TiO2, and TiO2 / Al / TiO2; and / or The functional layer includes an electronic functional layer, and the material of the electronic functional layer includes the organic material; Optionally, the functional layer further includes a light-emitting layer located between the anode and the electronic functional layer; optionally, the material of the light-emitting layer includes one or more of organic light-emitting materials and quantum dot light-emitting materials; the organic light-emitting material is selected from 4,4'-bis(N-carbazole)-1,1'-biphenyl:tris[2-(p-tolyl)pyridinium(III)], 4,4',4”-tris(carbazole-9-yl)triphenylamine:tris[2-(p-tolyl)pyridinium], diaromatic anthracene derivatives, stilbene aromatic derivatives, pyrene derivatives, fluorene derivatives, TBPe fluorescent materials, and TTPX fluorescent materials. The materials are selected from one or more of the following: TBRb fluorescent materials, DBP fluorescent materials, delayed fluorescence materials, TTA materials, TADF materials, polymers containing BN covalent bonds, HLCT materials, and Exciplex luminescent materials; the quantum dot luminescent materials are selected from one or more of the following: single-structure quantum dots, core-shell structure quantum dots, and perovskite semiconductor materials; the materials of the single-structure quantum dots, the core materials of the core-shell structure quantum dots, and the shell materials of the core-shell structure quantum dots are respectively selected from group II-VI compounds, group IV-VI compounds, group III-V compounds, and group I-III-VI compounds. One or more of the following; the shell of the core-shell quantum dot comprises one or more layers; the II-VI group compound is selected from 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, CdZnS The compounds are selected from one or more of the following: eS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and HgZnSTe; the IV-VI compounds are selected from one or more of the following: SnS, SnSe, SnTe, PbS, PbSe, PbTe, SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, SnPbSSe, SnPbSeTe, and SnPbSTe.The III-V 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. Several types; the I-III-VI group compounds are selected from one or more of CuInS2, CuInSe2, and AgInS2; the core-shell quantum dots are selected from one or more of CdSe / CdSeS / CdS, InP / ZnSeS / ZnS, CdZnSe / ZnSe / ZnS, CdSeS / ZnSeS / ZnS, CdSe / ZnS, CdSe / ZnSe / ZnS, ZnSe / ZnS, ZnSeTe / ZnS, CdSe / CdZnSeS / ZnS, and InP / ZnSe / ZnS; the perovskite semiconductor material is selected from doped or undoped inorganic perovskite semiconductors or organic-inorganic hybrid perovskite semiconductors; the general structural formula of the inorganic perovskite semiconductor is AMX3, where A is Cs; + Ion, M is a divalent metal cation selected from Pb 2+ Sn 2+ Cu 2+ Ni 2+ Cd 2+ Cr 2+ Mn 2+ Co 2+ Fe 2+ 、Ge 2+ Yb 2+ Eu 2+ One or more of them, where X is a halide anion selected from Cl. - ,Br - I - One or more of the following; the general structural formula of the organic-inorganic hybrid perovskite semiconductor is BMX3, where B is an organic amine cation selected from CH3(CH2). n-2 NH3 + Or [NH3(CH2)] n NH3] 2+ Where n≥2, M is a divalent metal cation selected from Pb 2+ Sn 2+ Cu 2 + Ni 2+ Cd 2+ Cr 2+ Mn 2+ Co 2+ Fe 2+ 、Ge 2+ Yb 2+ Eu 2+ One or more of them, where X is a halide anion selected from Cl. - ,Br - I - One or more of them; Optionally, the functional layer further includes a hole functional layer located between the anode and the light-emitting layer;Optionally, the material of the hole functional layer includes 4,4'-N,N'-dicarbazolyl-biphenyl, 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, 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(carbazolyl-9-yl)triphenylamine, trichloroisocyanuric acid, and terbium-doped phosphate-based green luminescent material. Materials, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzphenanthrene, 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(4-butylphenyl-diphenylamine), poly[bis(4-phenyl)(4-butylphenyl)amine], polyaniline, polypyrrole, poly(p-)phenylenevinylene, poly(phenylenevinylene), poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylenevinylene], poly[2-methoxy-5-(3',7'-dimethyloctyloxy] [N,N'-1,4-phenylenevinylene], copper phthalocyanine, aromatic tertiary amines, polynuclear aromatic tertiary amines, 4,4'-bis(p-carbazolyl)-1,1'-biphenyl compounds, N,N,N',N'-tetraarylbenzidine, PEDOT, PEDOT:PSS and its derivatives, PEDOT:PSS derivatives doped with s-MoO3, poly(N-vinylcarbazole) and its derivatives, polymethacrylate and its derivatives, poly(9,9-octylfluorene) and its derivatives, poly(spirofluorene) and its derivatives, N,N'-di(naphthyl-1-yl)-N,N'-diphenylbenzidine, spiroNPB, nanocrystalline diamond, microcrystalline cellulose and tetracyanoquinone dimethane, doped graphene, undoped graphene, doped The metal oxide particles are selected from one or more of the following: doped metal oxide particles, undoped metal oxide particles, metal sulfides, metal selenides, and metal nitrides. The metal oxides in the doped and undoped metal oxide particles each independently include one or more of MoO3, WO3, NiO, CrO3, CuO, and V2O5. The doping element in the doped metal oxide particles includes one or more of Mo, W, Ni, Cr, Cu, and V. The metal sulfides include one or more of CuS, MoS3, and WS3. The metal selenides include one or more of MoSe3 and WSe3. The metal nitrides include p-type gallium nitride.

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