Compound and organic light-emitting device thereof

Abstract

The invention belongs to the field of organic electroluminescence, and discloses a compound and an organic light-emitting device thereof. The compound has a structure as shown in a formula (1), wherein * represents a site where A and B are connected. The compound provided by the invention has a series of excellent physical and chemical characteristics, and has a good application prospect in the photoelectric field. Specifically, the compound has excellent photoelectric stability, can effectively resist performance degradation caused by illumination and current change, and ensures stable output of the device in long-time operation. An OLED device prepared from the compound has low driving voltage and high luminous efficiency, and meanwhile, the OLED device also has relatively long service life.

Description

Technical Field

[0001] This application belongs to the field of organic electroluminescence technology, and specifically relates to a compound and its organic light-emitting device. Background Technology

[0002] Currently, organic light-emitting diodes (OLEDs), as a next-generation display technology, are receiving increasing attention in both display and lighting technologies, with a very broad application prospect. However, compared with market application requirements, the performance of OLED devices, such as luminous efficiency, driving voltage, and lifespan, still needs further improvement.

[0003] Generally, the basic structure of an OLED device consists of thin films of various organic functional materials sandwiched between metal electrodes, much like a sandwich structure. Driven by an electric current, electrons and holes are injected from the anode and cathode, respectively. After traveling a certain distance, the electrons and holes recombine in the light-emitting layer and are released as light or heat, thus producing OLED light emission. Organic functional materials are the core components of organic electroluminescent devices, such as hole-blocking materials and electron transport materials. The thermal stability, photochemical stability, electrochemical stability, quantum yield, film-forming stability, crystallinity, and color saturation of these materials are all major factors affecting the device's performance.

[0004] However, there is still room for improvement in the currently reported organic functional materials. For example, existing technologies disclose compounds... compound or compounds These compounds have been studied and applied as electron transport materials, but their performance still needs improvement, especially in terms of meeting the requirements for lower operating voltage, higher device efficiency, and longer device lifetime. Further research and development are still needed. Summary of the Invention

[0005] This application aims to at least solve one of the aforementioned technical problems existing in the prior art. To this end, this application proposes a compound that, through the coordination between the ortho-substitution of cyano and deuterated aryl groups in the molecule, possesses advantages such as good film-forming properties, good optical, electrical, and thermal stability, high luminous efficiency, low voltage, and long lifetime. It can be used in organic light-emitting devices, especially as a hole blocking layer material and an electron transport layer material, and has the potential for application in the AMOLED industry.

[0006] The first aspect of this application provides a compound.

[0007] In some embodiments, the structure of the compound is shown in formula (1):

[0008]

[0009] Where * represents the site where A and B are connected;

[0010] Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C40 aromatic groups, or substituted or unsubstituted C3-C40 heteroaromatic groups;

[0011] Ar3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted benzophenanthryl, substituted or unsubstituted pyrene, substituted or unsubstituted fluoranyl, substituted or unsubstituted spiro[cyclohexane-1,9'-fluoren]yl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted indolocarbazolyl, substituted or unsubstituted imidazolyl, or a combination of two of the above.

[0012] Ar4 is selected from substituted phenyl, substituted diphenyl, substituted terphenyl, substituted naphthyl, substituted phenanthryl, substituted benzo[phenanthryl], substituted pyrene, substituted fluoranyl, substituted spiro[cyclohexane-1,9'-fluorenyl], substituted dibenzofuranyl, substituted dibenzothiopheneyl, substituted carbazolyl, substituted benzocarbazolyl, substituted indolocarbazolyl, substituted imidazolyl, or a combination of two of the above; the substitution in Ar4 indicates that it is substituted by at least one of deuterium, halogen, cyano, isocyano, C1-C6 alkyl, deuterated C1-C6 alkyl, C3-C16 cycloalkyl, deuterated C3-C16 cycloalkyl, and deuterated C3-C16 cycloalkyl, the number of substitutions is from monosubstituted to the maximum number of substitutions, and at least one substitution indicates that it is substituted by deuterium;

[0013] L is selected from single-bonded, substituted or unsubstituted C6-C40 aromatic groups, or substituted or unsubstituted C3-C40 heteroaromatic groups;

[0014] m is selected from 0 or 1;

[0015] When m is selected from 0, at least one of Ar1, Ar2, Ar3, and Ar4 is substituted with at least one cyano group;

[0016] The substitutions in Ar1 to Ar3 and L each independently represent substitution by at least one of deuterium, halogen, cyano, isocyano, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 hydrocarbon substituted or unsubstituted C6-C30 aryl, C1-C6 hydrocarbon substituted or unsubstituted C3-C30 heteroaryl, with the number of substitutions ranging from monosubstituted to the maximum number of substitutions;

[0017] The heteroatom in the heteroaryl, heteroaryl, heteroalkyl, or heterocycloalkyl group is independently selected from at least one of O, S, N, Se, Si, and Ge;

[0018] The compound does not have the following structure:

[0019]

[0020] Compared with the prior art, this application has at least the following beneficial technical effects:

[0021] The compound provided in this application incorporates a cyano group and an aryl group with a deuterated position. Through this structural design, the resulting compound exhibits a series of superior physicochemical properties and shows promising application prospects in the optoelectronic field.

[0022] Specifically, the compounds in this application exhibit excellent film-forming properties and outstanding optical, electrical, and thermal stability, effectively resisting performance degradation caused by changes in light and current, ensuring stable output of the device during long-term operation. Therefore, these compounds can be used in organic light-emitting devices, providing better performance, particularly for preparing emissive layer materials, hole-blocking layer materials, and electron transport layer materials. The organic electroluminescent devices prepared using these compounds possess low driving voltage and high luminous efficiency, with lower operating voltage, higher current efficiency, and longer lifetime, showing potential for application in the AMOLED industry.

[0023] Additional aspects and advantages of this application will be set forth in part in the description which follows, and in part will be obvious from the description, or may be learned by practice of this application. Attached Figure Description

[0024] The present application will be further described below with reference to the accompanying drawings and embodiments, wherein:

[0025] Figure 1 This is a schematic diagram of the stacked structure of an organic electroluminescent device according to an embodiment of this application.

[0026] right Figure 1 The numbering in the code is explained as follows:

[0027] 1-Anode, 2-Hole injection layer, 3-First hole transport layer, 4-Second hole transport layer, 5-Light emission layer, 6-Hole blocking layer, 7-Electron transport layer, 8-Electron injection layer, 9-Cathode. Detailed Implementation

[0028] In the description of this application, the reference to terms such as "some implementations" or "some embodiments" indicates that a specific feature, structure, material, or characteristic described in connection with that embodiment or example is included in at least one embodiment or example of this application. In this specification, the illustrative expressions of the above terms do not necessarily refer to the same embodiment or example. Furthermore, the specific features, structures, materials, or characteristics described may be combined in any suitable manner in one or more embodiments or examples.

[0029] In the description of this application, the use of terms such as first, second, third, etc., is only for the purpose of distinguishing technical features and should not be construed as indicating or implying relative importance, or implicitly indicating the number of technical features indicated, or implicitly indicating the order of the technical features indicated.

[0030] Unless otherwise stated, the scientific and technical terms used herein have the meanings commonly understood by those skilled in the art. However, for a better understanding of this application, definitions of some terms are provided below. In the event that the definitions of terms provided herein differ from the meanings commonly understood by those skilled in the art, the definitions and interpretations provided herein shall prevail.

[0031] The alkyl group is a straight-chain or branched saturated hydrocarbon group, and the number of carbon atoms can be 1 to 60, 1 to 40, 1 to 30, 1 to 20, 1 to 12, 1 to 6, or 1 to 3. Non-limiting examples of alkyl groups include methyl, ethyl, propyl, butyl, heptyl, decyl, etc.

[0032] Cycloalkyl groups are alkyl groups with cyclic structures, which can include monocyclic, polycyclic, and spiroalkyl groups. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, and 2-norbornyl.

[0033] Examples of alkenyl groups include vinyl, propenyl, allyl, 1-butadienyl, 2-butadienyl, 1-hextrienyl, 2-hextrienyl, 3-hextrienyl, etc.

[0034] Heteroalkyl refers to an alkyl group in which at least one carbon atom is replaced by a non-carbon atom, excluding cases where the carbon atom serving as a linking site is replaced by a non-carbon atom (e.g., alkoxy, alkylsilyl). Examples include mercaptomethylmethane, methoxymethane, ethoxymethane, tert-butoxymethane, N,N-dimethylmethane, epoxybutane, epoxypentane, epoxyhexane, etc., with methoxymethane and epoxypentane being preferred.

[0035] A heterocyclic alkyl group is defined as a cycloalkyl group in which at least one carbon atom is replaced by a non-carbon atom, which may be selected from at least one of O, S, N, P, B, Si, Ge, or Se. The number of carbon atoms in a heterocyclic alkyl group may be 3 to 30, 3 to 20, 3 to 12, 3 to 10, or 3 to 6. Non-limiting examples of heterocyclic alkyl groups include epoxide butyl, epoxide pentyl, and epoxide hexyl.

[0036] Aromatic groups are aromatic hydrocarbon groups derived from aromatic ring compounds by removing one hydrogen atom. They can be monocyclic or polycyclic. At least one ring in a polycyclic aryl group is an aromatic ring system. Multiple rings in a polycyclic aryl group can be linked together by single bonds or can be fused together. For example, aryl groups are selected from phenyl, naphthyl, anthracene, phenanthrene, tetraphenyl, pyrene, dinaphthylphenyl, acenaphthyl, benzo[g]pyrene, benzo[g]phenanthrene, benzo[g]triylyl, fluorene, spirodifluorene, benzo[g]fluorene, dibenzo[g]fluorene, biphenyl, triphenyl, tetraphenyl, or fluoranyl. Among them, benzo[g]phenanthrene includes 1,2-benzo[g]phenanthrene (…). (e.g., 3,4-benzophenanthryl, 9,10-benzophenanthryl).

[0037] A heteroaryl group is defined as an aryl group in which at least one carbon atom is replaced by a non-carbon atom. The non-carbon atom can be a monovalent group selected from heterocyclic aromatic systems containing O, S, N, Se, Si, or Ge, but does not include cases where the aryl group uses a non-carbon atom as a linking site (e.g., aryloxy, arylsilyl, arylamine). Examples include pyrrole, pyrrolopyrrole, furanopyrrole, thienopyrrole, pyridyl, pyrazolyl, pyrimidinyl, pyrazinyl, triazinyl, pyridazinyl, phenazinyl, phenothiazinyl, phenoxazinyl, indole, isoindole, imidazolyl, benzimidazinyl, triazolyl, tetrazolyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, furanofuranyl, azadibenzofuranyl, thienofuranyl, diazadibenzofuranyl, and benzo[B]naphtho[1,2-D]furan. yl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, quinazolinoneyl, carbazoyl, azacarbazoyl, diazacarbazoyl, phenanthrynyl, primidinyl, acridineyl, dihydroacridinyl, phenanthrynyl, oxazolinyl, oxazolyl, oxadiazolyl, benzoisooxazolyl, thiazoyl, benzothiazoyl, benzoisothiazoyl, pyrroloimidazoyl, furanyl, thienyl, benzothiaphenyl, dibenzothiaphenyl, azadibenzothiaphenyl, diazadibenzothiaphenyl, thienothiaphenyl or o-diazanaphthyl.

[0038] Arylphosphinyl, arylamine, and arylboryl groups refer to groups formed by the combination of an aromatic ring with a phosphinyl, amino, or boronyl group, respectively. Among them, arylphosphinyl groups include monoarylphosphinyl and diarylphosphinyl groups.

[0039] Fused rings refer to polycyclic compounds formed by the fusion of two or more ring structures (such as aromatic rings and heteroaromatic rings) through the sharing of adjacent ring atoms (such as carbon-carbon bonds and carbon-nitrogen bonds).

[0040] Fusing is a way in which aromatic rings and / or aromatic heterocycles, aromatic rings and cycloalkanes, or aromatic heterocycles and cycloalkanes are bonded together by sharing a side.

[0041] arylene and heteroarylene correspond to divalent groups in aryl and heteroaryl structures, respectively.

[0042] The phrase "a to b carbons of R group with substituted or unsubstituted carbons" refers to the number of carbons when the R group is unsubstituted, excluding the number of carbons of the substituents when the R group is substituted.

[0043] "Substitution" in "substituted or unsubstituted" means that one or more hydrogen atoms are replaced by other atoms or functional groups (i.e., substituents), and unless otherwise defined, it also includes the replacement of one or more hydrogen atoms by groups formed by the linkage of two or more of the substituents mentioned above.

[0044] Maximum number substitution refers to the maximum number of hydrogen atoms contained in the group when there are no substituents other than hydrogen.

[0045] The combination of two groups in groups such as phenyl, biphenyl, naphthyl, and anthracene refers to the connection or fusion of two groups through chemical bonds. Specifically, chemical bonding can be a single bond; for example, a phenyl and naphthyl group combined by a single bond results in a naphthyl-substituted phenyl group. They can also be fused together to form anthracene or phenanthrene groups, but are not limited to this connection method.

[0046] structure This indicates that it can be attached to any connectable site on the benzene ring, including the ortho, meta, and para positions of the ring atom attached to R; the setting of R is only for better understanding of the substitution position and is not intended to be any limitation.

[0047] The CAS number for spiro[cyclohexane-1,9'-fluorene] is 7258-61-9. The spiro[cyclohexane-1,9'-fluorene] group is a monovalent group formed after spiro[cyclohexane-1,9'-fluorene] loses one hydrogen atom.

[0048] The following will describe the concept and technical effects of this application clearly and completely with reference to specific embodiments, so as to fully understand the purpose, features and effects of this application.

[0049] The first aspect of this application provides a compound.

[0050] In some embodiments, the structure of the compound is shown in formula (1):

[0051]

[0052] Where * represents the site where A and B are connected;

[0053] Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C40 aromatic groups, or substituted or unsubstituted C3-C40 heteroaromatic groups;

[0054] Ar3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted benzophenanthryl, substituted or unsubstituted pyrene, substituted or unsubstituted fluoranyl, substituted or unsubstituted spiro[cyclohexane-1,9'-fluoren]yl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted indolocarbazolyl, substituted or unsubstituted imidazolyl, or a combination of two of the above.

[0055] Ar4 is selected from substituted phenyl, substituted diphenyl, substituted terphenyl, substituted naphthyl, substituted phenanthryl, substituted benzo[phenanthryl], substituted pyrene, substituted fluoranyl, substituted spiro[cyclohexane-1,9'-fluorenyl], substituted dibenzofuranyl, substituted dibenzothiopheneyl, substituted carbazolyl, substituted benzocarbazolyl, substituted indolocarbazolyl, substituted imidazolyl, or a combination of two of the above; the substitution in Ar4 indicates that it is substituted by at least one of deuterium, halogen, cyano, isocyano, C1-C6 alkyl, deuterated C1-C6 alkyl, C3-C16 cycloalkyl, deuterated C3-C16 cycloalkyl, and deuterated C3-C16 cycloalkyl, the number of substitutions is from monosubstituted to the maximum number of substitutions, and at least one substitution indicates that it is substituted by deuterium;

[0056] L is selected from single-bonded, substituted or unsubstituted C6-C40 aromatic groups, or substituted or unsubstituted C3-C40 heteroaromatic groups;

[0057] m is selected from 0 or 1;

[0058] When m is selected from 0, at least one of Ar1, Ar2, Ar3, and Ar4 is substituted with at least one cyano group;

[0059] The substitutions in Ar1 to Ar3 and L each independently represent substitution by at least one of deuterium, halogen, cyano, isocyano, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 hydrocarbon substituted or unsubstituted C6-C30 aryl, C1-C6 hydrocarbon substituted or unsubstituted C3-C30 heteroaryl, with the number of substitutions ranging from monosubstituted to the maximum number of substitutions;

[0060] The heteroatom in the heteroaryl, heteroaryl, heteroalkyl, or heterocycloalkyl group is independently selected from at least one of O, S, N, Se, Si, and Ge;

[0061] The compound does not have the following structure:

[0062]

[0063] In some embodiments, formula (1) is selected from the structures shown in formulas (A-1) to (A-3):

[0064]

[0065] In some embodiments, formula (1) is selected from the structures shown in formulas (A-4) to (A-6):

[0066]

[0067] In some embodiments, m = 1, and the substituents of Ar1 to Ar4 do not contain cyano groups;

[0068] Alternatively, m = 0, Ar1 and / or Ar2 are substituted with at least one cyano group;

[0069] Alternatively, m = 0, Ar3 and / or Ar4 are substituted with at least one cyano group.

[0070] In some specific embodiments, the number of cyano groups in Ar1 to Ar4 ranges from monosubstituted to a maximum number of substituted groups. Specifically, the number of cyano groups in Ar1 to Ar4 ranges from 1 to 10, for example, the number of substituted groups is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0071] In some embodiments, the Ar3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted benzophenanthryl, substituted or unsubstituted pyrene, substituted or unsubstituted fluoranyl, substituted or unsubstituted spiro[cyclohexane-1,9'-fluorenyl], substituted or unsubstituted dibenzofuranyl, or a combination of two of the above.

[0072] In some embodiments, the Ar4 is selected from substituted phenyl, substituted diphenyl, substituted terphenyl, substituted naphthyl, or a combination of two of the above.

[0073] In some embodiments, equation (1) satisfies at least one of the following conditions:

[0074] (1) Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C30 aromatic groups or substituted or unsubstituted C3-C30 heteroaromatic groups;

[0075] (2) L is selected from single bonds, substituted or unsubstituted C6-C30 aromatic groups, or substituted or unsubstituted C3-C30 heteroaromatic groups;

[0076] (3) The substitutions in Ar1 to Ar3 and L each independently represent substitution by at least one of deuterium, halogen, cyano, isocyano, C1-C4 alkyl, C3-C12 cycloalkyl, C1-C4 hydrocarbon substituted or unsubstituted C6-C25 aryl, C1-C4 hydrocarbon substituted or unsubstituted C3-C25 heteroaryl, with the number of substitutions ranging from monosubstituted to the maximum number of substitutions.

[0077] In some embodiments, equation (1) satisfies at least one of the following conditions:

[0078] (1) Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C25 aromatic groups or substituted or unsubstituted C3-C25 heteroaromatic groups;

[0079] (2) L is selected from single bond, substituted or unsubstituted C6-C20 aromatic groups, or substituted or unsubstituted C3-C20 heteroaromatic groups;

[0080] (3) The substitutions in Ar1 to Ar3 and L each independently represent substitution by at least one of deuterium, halogen, cyano, isocyano, C1-C4 alkyl, C3-C10 cycloalkyl, C1-C4 hydrocarbon substituted or unsubstituted C6-C20 aryl, C1-C4 hydrocarbon substituted or unsubstituted C3-C20 heteroaryl, with the number of substitutions ranging from monosubstituted to the maximum number of substitutions;

[0081] (4) The substitution in Ar4 means that it is substituted by at least one of deuterium, halogen, cyano, isocyano, C1-C3 alkyl, deuterated C1-C3 alkyl, C3-C6 cycloalkyl, deuterated C3-C6 cycloalkyl, and the number of substitutions is from monosubstituted to the maximum number of substitutions, and at least one substitution means that it is substituted by deuterium.

[0082] In some embodiments, the substitution in Ar4 represents substitution by at least one of deuterium, halogen, cyano, isocyano, methyl, deuterated methyl, ethyl, deuterated ethyl, propyl, deuterated propyl, cyclopropyl, cyclohexyl, deuterated cyclopropyl, and deuterated cyclohexyl, the number of substitutions ranging from monosubstituted to a maximum number of substitutions, and at least one substitution represents substitution by deuterium.

[0083] In some embodiments, equation (1) satisfies at least one of the following conditions:

[0084] (1) Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C20 aromatic groups or substituted or unsubstituted C3-C20 heteroaromatic groups;

[0085] (2) L is selected from single bonds, substituted or unsubstituted C6-C12 aromatic groups, or substituted or unsubstituted C3-C12 heteroaromatic groups.

[0086] In some embodiments, equation (1) satisfies at least one of the following conditions:

[0087] (1) Ar1 and Ar2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted fluoranyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted indolocarbazolyl, or a combination of two of the above.

[0088] (2) L is selected from single bond, phenylene, biphenylene or naphthylene;

[0089] (3) The substitutions in Ar1 to Ar3 each independently represent substitution by at least one of deuterium, halogen, cyano, isocyano, methyl, ethyl, propyl, butyl, cyclopropyl, cyclohexyl, adamantyl, C1-C4 hydrocarbon substituted or unsubstituted phenyl, C1-C4 hydrocarbon substituted or unsubstituted biphenyl, C1-C4 hydrocarbon substituted or unsubstituted naphthyl, C1-C4 hydrocarbon substituted or unsubstituted pyridyl, C1-C4 hydrocarbon substituted or unsubstituted pyrimidinyl and C1-C4 hydrocarbon substituted or unsubstituted carbazolyl, with the number of substitutions ranging from monosubstituted to the maximum number of substitutions;

[0090] (4) The Ar4 is selected from substituted phenyl, substituted diphenyl, substituted triphenyl, substituted naphthyl, or a combination of two of the above; the substitution is deuterium substitution, and the number of substitutions ranges from monosubstituted to the maximum number of substitutions; or:

[0091] The Ar4 is selected from substituted phenyl, substituted diphenyl, substituted terphenyl, substituted naphthyl, or a combination of two of the above; the substitution is cyano substitution and deutero substitution, the number of cyano substitutions is 1, and the number of deutero substitutions is from monosubstituted to the maximum number of substitutions.

[0092] Specifically, in the Ar4, the number of deuterium substitutions is 1 to 20, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20.

[0093] Specifically, the substituted or unsubstituted fluorenyl group includes at least one of 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, phenyl-substituted fluorenyl, cyano-substituted fluorenyl, deuterated fluorenyl, and halofluorenyl.

[0094] It should be understood that the C1-C4 hydrocarbon groups in "C1-C4 hydrocarbon groups substituted or unsubstituted" include methyl, ethyl, propyl or butyl.

[0095] In some embodiments, the substitutions in Ar1 to Ar3 each independently represent substitution by at least one of deuterium, halogen, cyano, isocyano, methyl, ethyl, propyl, butyl, cyclopropyl, cyclohexyl, adamantyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, carbazolyl, and imidazolyl, with the number of substitutions ranging from monosubstituted to the maximum number of substitutions.

[0096] In some embodiments, the substitution in Ar4 indicates that it is substituted by at least one of deuterium, cyano, and isocyano, and the number of substitutions ranges from monosubstituted to a maximum number of substitutions, with at least one substitution indicating that it is substituted by deuterium.

[0097] In some embodiments, the compound is selected from one of the following structures, or one of the following structures in which hydrogen is partially or completely substituted by deuterium or fluorine:

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107] A second aspect of this application provides an organic light-emitting device.

[0108] In some embodiments, the organic light-emitting device includes a cathode and an anode, the cathode being disposed opposite to the anode, and a functional layer being provided between the cathode and the anode, the functional layer comprising the compound described in the first aspect of this application.

[0109] In some embodiments, the functional layer includes a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer; at least one of the light-emitting layer, the hole blocking layer, and the electron transport layer includes the compound.

[0110] In some embodiments, the functional layer includes an electron transport layer, wherein the electron transport layer includes the compound.

[0111] In some embodiments, the mass content of the compound in the functional layer is 1% to 100%. For example, the mass content of the compound can be 1%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or 100%, or other ranges consisting of these values, such as 10–100%, 30–100%, 50–100%, 70–100%, 80–100%, or 90–100%.

[0112] In some embodiments, the organic light-emitting device is an organic electroluminescent device.

[0113] It should be noted that the embodiments described in this application are exemplary and are only for the purpose of facilitating understanding of the technical application. They should not be considered as specific limitations on this application. Obviously, the described embodiments are only a part of the embodiments of this application, not all of them. Other embodiments obtained by those skilled in the art based on the embodiments of this application without creative effort are all within the scope of protection of this application. Unless otherwise specified, the experimental methods used in the embodiments are conventional methods; the materials, reagents, or devices used are all commercially available unless otherwise specified. Unless otherwise specified, the same parameter value is the same in all embodiments.

[0114] In the embodiments described below, the raw materials and solvents involved in the synthesis of the compounds in this application were all purchased from suppliers well known to those skilled in the art, such as Alfa and Acros.

[0115] The following embodiments of this application provide methods for synthesizing the following compounds and their related test results.

[0116]

[0117] Synthesis of Compound 1

[0118] Synthesis route:

[0119]

[0120] Synthesis of compounds 1-3

[0121] Compound 1-1 (15.00 g, 80.63 mmol, CAS: 771534-56-6), compound 1-2 (12.61 g, 80.63 mmol, CAS: 3900-89-8), [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (0.59 g, 0.42 mmol), potassium carbonate (24.51 g, 177.38 mmol), 1,4-dioxane (250 ml), and deionized water (50 ml) were added to a 500 ml three-necked round-bottom flask. The flask was purged with nitrogen three times. The system was then heated to 75 °C and reacted for 6 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:20 as the developing solvent). Compound 1-1 was completely consumed.

[0122] Cool to room temperature, concentrate under reduced pressure to remove some of the solvent, add ethyl acetate (200 ml), wash three times with deionized water (50 ml * 3), separate the contents, dry-pick up the sample onto a silica gel column, and perform silica gel column chromatography purification (200-300 mesh silica gel, ethyl acetate: n-hexane = 1:20 as eluent). After elution, concentrate under reduced pressure at 60 °C for 1 hour to obtain a white solid as compound 1-3 (12.49 g, purity: 99.44%, yield: 71.16%), mass spectrometry: 218.06 (M+H).

[0123] Synthesis of compounds 1-5

[0124] Compounds 1-3 (12.00 g, 55.12 mmol), compound 1-4 (14.00 g, 55.12 mmol), tris(dibenzylacetone)palladium (0.50 g, 0.55 mmol), 2-dicyclohexylphosphine-2′,4′,6′-triisopropylbiphenyl (0.53 g, 1.1 mmol), potassium acetate (13.53 g, 137.81 mmol), and 1,4-dioxane (300 ml) were added to a 500 ml three-necked round-bottom flask. The flask was purged with nitrogen three times, and then the system was heated to 100 °C and reacted for 2 hours. The reaction was monitored by TLC (using n-hexane:ethyl acetate = 15:1 as the developing solvent). Compounds 1-3 were completely consumed.

[0125] Cool to 60℃, concentrate under reduced pressure to remove solvent, add ethyl acetate (250ml), wash three times with deionized water (50ml*3), separate the liquid, mix with silica gel, dry-load column, and perform silica gel column chromatography purification (200-300 mesh silica gel, n-hexane:ethyl acetate = 15:1 as eluent). After elution, concentrate under reduced pressure at 60℃ for 1 hour to obtain target compounds 1-5 (12.96g, purity: 99.14%, yield: 76.03%), mass spectrometry: 310.18 (M+H).

[0126] Synthesis of compounds 1-8

[0127] Following the synthesis and purification methods of compounds 1-3, only the corresponding raw materials need to be changed to obtain target compound 8 (8.77 g, purity: 99.20%, yield: 72.92%), mass spectrometry: 510.13 (M+H). Among them, compound 6 CAS: 402936-15-6; compound 7 CAS: 1073062-42-6.

[0128] Synthesis of Compound 1

[0129] Compounds 1-8 (8.50 g, 16.67 mmol), 1-5 (5.15 g, 16.67 mmol), dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine-palladium (0.12 g, 0.17 mmol), potassium carbonate (5.76 g, 41.67 mmol), 1,4-dioxane (200 ml), and deionized water (50 ml) were added to a 500 ml three-necked round-bottom flask. The mixture was purged with nitrogen three times under vacuum, and the oil temperature was raised to 75 °C. The reaction was carried out for 6 hours and monitored by TLC (using dichloromethane:n-hexane = 1:5 as the developing solvent). Heating was stopped after compounds 1-8 were completely consumed.

[0130] After the reaction was complete, a large amount of solid precipitated. This solid was directly filtered to obtain a white solid. Toluene (80 ml) was added, and the mixture was heated to 130°C to dissolve and clarify. The solid was filtered once onto silica gel (20 g, 200-300 mesh silica gel column). The filtrate was cooled to room temperature and stirred for 2 hours. Filtering yielded a white solid. Toluene (100 ml) was added, and the oil temperature was raised to 130°C to dissolve and clarify. The mixture was then allowed to cool naturally to room temperature and stirred for 2 hours. Filtering was performed, and the filter cake was dried under vacuum at 90°C for 3 hours to obtain a white solid, compound 1 (7.62 g, purity: 99.92%, yield: 69.61%). The 7.62 g crude compound 1 was sublimated to obtain sublimed pure compound 1 (5.03 g, purity: 99.95%, yield: 66.01%), mass spectrometry: 657.25 (M+H).

[0131] 1 H NMR(400MHz, CDCl3) δ8.66(t,J=2.2Hz,1H),8.43–8.38(m,5H),8.16(d,J=2.3Hz,1H),8.04–7.99( m,2H),7.67(dd,J=7.3,2.4Hz,1H),7.60(d,J=7.1Hz,1H),7.56–7.45(m,12H),7.40-7.35(m,1H).

[0132] Synthesis of compounds 2-5, 8-9, 11, and 18

[0133] The synthesis methods for compounds 2, 3, 4, 5, 8, 9, 11, and 18 are the same as those for compound 1, but the raw materials used are different. These raw materials are shown in Table 1 below. In Table 1, raw material 1, raw material 2, raw material 3, and raw material 4 represent the compounds used to replace compounds 1-1, 1-2, 1-4, and 1-8 in the synthetic route of compound 1, respectively.

[0134] Table 1. Synthetic raw materials and characterization information for compounds 2-5, 8-9, 11, and 18.

[0135]

[0136]

[0137]

[0138] The synthesis of some of the intermediate compounds in Table 1 is explained below:

[0139] Synthesis of intermediate compound 4-3

[0140] Synthesis route:

[0141]

[0142] Synthesis of compound 4-3

[0143] Following the synthesis and purification methods of compounds 1-3, only the corresponding raw materials need to be changed to obtain the target compound 4-3 (10.16 g, purity: 99.37%, yield: 70.25%), mass spectrometry: 597.18 (M+H). Compound 4-1 has the CAS number 1644541-79-6.

[0144] Synthesis of intermediate compound 8-3

[0145] Synthesis route:

[0146]

[0147] Synthesis of compound 8-3

[0148] Following the synthesis and purification methods of compounds 1-3, only the corresponding raw materials need to be changed to obtain the target compound 8-3 (11.42 g, purity: 99.16%, yield: 68.54%), mass spectrometry: 648.21 (M+H). Compound 8-1 has CAS code 2135784-08-4; compound 8-2 has CAS code 663954-31-2.

[0149] Synthesis of intermediate compound 9-2

[0150] Synthesis route:

[0151]

[0152] Synthesis of compound 9-2

[0153] Following the synthesis and purification methods of compounds 1-3, only the corresponding raw materials need to be changed to obtain the target compound 9-2 (9.58 g, purity: 99.43%, yield: 72.51%), mass spectrometry: 597.18 (M+H). Compound 9-1 has the CAS number 1352715-67-3.

[0154] Synthesis of intermediate compound 11-2

[0155] Synthesis route:

[0156]

[0157] Synthesis of compound 11-2

[0158] Following the synthesis and purification methods of compounds 1-3, only the corresponding raw materials need to be changed to obtain the target compound 11-2 (10.09 g, purity: 99.30%, yield: 70.33%), mass spectrometry: 597.18 (M+H).

[0159] Synthesis of compounds 6-7, 10, 12-17, and 19-21

[0160] Synthesis of Compound 6

[0161] Synthesis route:

[0162]

[0163] Synthesis of compound 6-2

[0164] Following the synthesis and purification methods of compounds 1-3, only the corresponding raw materials need to be changed to obtain the target compound 6-2 (16.58 g, purity: 99.42%, yield: 73.32%), mass spectrometry: 274.13 (M+H). Compound 6-1 has the CAS number 142475-00-1.

[0165] Synthesis of compound 6-3

[0166] Following the synthesis and purification methods of compounds 1-5, only the corresponding raw materials need to be changed to obtain target compounds 6-3 (15.83g, purity: 99.21%, yield: 74.15%), mass spectrometry: 366.25 (M+H).

[0167] Synthesis of compound 6-6

[0168] Following the synthesis and purification methods of compounds 1-3, only the corresponding raw materials need to be changed to obtain the target compound 6-6 (14.39 g, purity: 99.33%, yield: 69.80%), mass spectrometry: 502.22 (M+H). Compound 6-5 has the CAS number 1817642-12-8.

[0169] Synthesis of compounds 6-7

[0170] Following the synthesis and purification methods of compounds 1-5, only the corresponding raw materials need to be changed to obtain target compounds 6-7 (11.94 g, purity: 99.15%, yield: 72.14%), mass spectrometry: 594.35 (M+H).

[0171] Synthesis of Compound 6

[0172] Compounds 6-7 (11.00 g, 18.53 mmol), 6-8 (6.83 g, 18.53 mmol, CAS: 2260561-71-3), tetra(triphenylphosphine)palladium (0.21 g, 0.19 mmol), sodium hydroxide (1.63 g, 40.77 mmol), tetrahydrofuran (200 ml), and deionized water (50 ml) were added to a 500 ml three-necked round-bottom flask. The mixture was purged with nitrogen three times under vacuum, and the oil temperature was raised to 75 °C. The reaction was carried out for 6 hours and monitored by TLC (ethyl acetate: n-hexane = 1:15 as the developing solvent). Heating was stopped after compound 6-7 was completely consumed.

[0173] After the reaction was complete, a large amount of solid precipitated. The solid was directly filtered to obtain a white solid. Dichloromethane (300 ml) was added to dissolve and clarify the solid. The solid was filtered once with silica gel (60 g, 200-300 mesh silica gel column). The filtrates were combined and concentrated at 65 °C for 1 hour to obtain a white solid. Toluene (100 ml) was added and the oil temperature was raised to 105 °C to dissolve and clarify the solid. The solid was allowed to cool naturally to room temperature and stirred for 1 hour. The solid was then filtered and dried under vacuum at 70 °C for 3 hours to obtain a white solid, which was compound 6 (10.05 g, purity: 99.90%, yield: 67.79%). Mass spectrometry: 800.37 (M+H).

[0174] 1H NMR (400MHz, CDCl3) δ8.67(t,J=2.2Hz,1H),8.45(t,J=2.2Hz,1H),8.43–8.39(m,2H),8.33(t,J=2.1Hz,1H),8.0 5–8.01(m,2H),7.86–7.83(m,2H),7.79–7.75(m,2H),7.67–7.58(m,7H),7.56–7.42(m,10H),7.40–7.36(m,1H).

[0175] Synthesis of compounds 7, 10, 12-17, and 19-21

[0176] The synthesis methods for compounds 7, 10, 12, 13, 14, 15, 16, 17, 19, 20, and 21 are the same as those for compound 6, but the starting materials used are different. These starting materials are shown in Table 2 below. In Table 2, starting materials 5, 6, 7, 8, and 9 represent the compounds used to replace compounds 6-1, 1-2, 1-4, 6-5, and 6-8 in the synthetic route of compound 6, respectively.

[0177] Table 2. Synthetic raw materials and characterization information for compounds 7, 10, 12-17, and 19-21

[0178]

[0179]

[0180]

[0181] The synthesis of some of the intermediate compounds in Table 2 is explained below:

[0182] Synthesis of intermediate compound 7-3

[0183] Synthesis route:

[0184]

[0185] Synthesis of Compound 7-3

[0186] Following the synthesis and purification methods of compounds 1-3, only the corresponding raw materials need to be changed to obtain the target compound 7-3 (12.17 g, purity: 99.37%, yield: 72.51%), mass spectrometry: 393.01 (M+H). Compound 7-1 has the CAS code 870774-25-7.

[0187] Synthesis of intermediate compound 15-3

[0188] Synthesis route:

[0189]

[0190] Synthesis of Compound 15-3

[0191] Following the synthesis and purification methods of compounds 1-3, only the corresponding raw materials need to be changed to obtain the target compound 15-3 (10.44 g, purity: 99.13%, yield: 70.20%), mass spectrometry: 445.11 (M+H). Compound 15-1 has CAS: 10202-45-6; compound 15-2 has CAS: 1130760-55-2.

[0192] Synthesis of intermediate compound 21-3

[0193] Synthesis route:

[0194]

[0195] Synthesis of compound 21-3

[0196] Following the synthesis and purification methods of compounds 1-3, only the corresponding raw materials need to be changed to obtain the target compound 21-3 (11.73g, purity: 99.38%, yield: 72.61%), mass spectrometry: 291.95 (M+H).

[0197] Application examples

[0198] Fabrication of organic electroluminescent devices:

[0199] In some embodiments, such as Figure 1 As shown, Figure 1 This is a schematic diagram of the stacked structure of a light-emitting device. The organic electroluminescent device includes an anode 1, a hole injection layer 2 (HIL), a first hole transport layer 3 (HTL1), a second hole transport layer 4 (HTL2), a light-emitting layer 5, a hole blocking layer 6 (HBL), an electron transport layer 7 (ETL), an electron injection layer 8 (EIL), and a cathode 9, which are stacked together.

[0200] The fabrication method of organic electroluminescent devices includes the following steps:

[0201] A 50mm*50mm*1.0mm glass substrate with an ITO (100nm) transparent electrode was ultrasonically cleaned in ethanol for 10 minutes, dried at 150 degrees Celsius, and then treated with N2 Plasma for 30 minutes.

[0202] The glass substrate (anode 1) with ITO transparent electrode after the above treatment is mounted on the substrate support of the vacuum evaporation apparatus, and compound HTM1 and PD (weight ratio of 97:3) are co-evaporated on the side with transparent electrode line in a manner that covers the transparent electrode to form a 5nm thick HIL.

[0203] Compound HTM1 was deposited on the surface of HIL to form HTL1, and the film thickness of HTL1 was 60 nm.

[0204] Compound HTM2 was deposited on the surface of HTL1 to form HTL2, and the thickness of HTL2 film was 10 nm.

[0205] On the surface of HTL2, the host material and dopant material are deposited by co-evaporation to form the light-emitting layer 5, wherein the thickness of the light-emitting layer 5 is 20nm, and the weight ratio of the host material and the dopant material is 97%:3%.

[0206] HBL (5nm) is deposited on the surface of the light-emitting layer 5 to form a hole blocking layer 6;

[0207] ETL:Liq (weight ratio of 50:50, 30nm) is deposited on the surface of hole blocking layer 6 according to the combination in Table 2 below to form electron transport layer 7 (ETL is the electron transport material in Table 2 below);

[0208] Liq is deposited on the surface of electron transport layer 7 to form EIL, and the thickness of EIL is 1 nm.

[0209] Al is deposited on the surface of EIL to form cathode 9, which has a thickness of 100 nm.

[0210]

[0211] The devices prepared above were subjected to device performance testing. In each embodiment and comparative example, a constant current power supply (Keithley 2400) was used, a fixed current density was applied to the light-emitting element, and the emission spectrum was measured using a spectroradiometer (CS2000). Simultaneously, a current density of 10 mA / cm² was measured. 2 Drive voltage and current efficiency under these conditions, and testing at 20mA / cm 2 Under the condition of 90% of the initial brightness, the brightness decay time (LT90) is used.

[0212] In this study, the electron transport layer material of Examples 1-21 was compound 1-21, and the electron transport layer material of Comparative Examples 1-6 was comparative compound 1-6.

[0213] All data are referenced to Comparative Example 1, and the results are shown in Table 3 below.

[0214] Table 3. Device performance test results for the examples and comparative examples.

[0215]

[0216]

[0217] As can be seen from the data comparison in Table 3, when the compounds of this application are used as electron transport layers in organic electroluminescent devices, although they also contain cyano groups in their structures compared with comparative compounds 1-4, the introduction of deuterated aryl ortho-substitution in the compounds of this application prevents material aggregation and ensures good transport. In particular, the deuteration improves the device lifetime. In addition, the compounds of this application also show higher efficiency and longer lifetime compared with comparative compound 5, which demonstrates the excellent performance and broad application prospects of the compounds of this application.

[0218] In summary, the compounds provided in this application possess advantages such as good optical, electrical, and thermal stability, and good film-forming properties, making them suitable for use in organic light-emitting devices (OLEDs). OLEDs prepared from these compounds exhibit advantages such as low voltage, long lifetime, and high luminous efficiency. In particular, when used as electron transport materials, they have the potential for application in the AMOLED industry.

[0219] Furthermore, since it is impossible to exhaustively list all the compounds in this application, the table above only lists the properties of some compounds or devices in this application. However, within the scope of protection claimed in this application, for example, the compounds with specific structural formulas given in this application all have the characteristics of high optical, electrical, and thermal stability, good film-forming properties, low driving voltage, high luminous efficiency, and long device life.

[0220] The above embodiments are preferred embodiments of this application, but the implementation of this application is not limited to the above embodiments. Any changes, modifications, substitutions, combinations, or simplifications made without departing from the spirit and principle of this application shall be considered equivalent substitutions and shall be included within the protection scope of this application.

Claims

1. A compound, characterized in that, The structure of the compound is shown in formula (1): Where * represents the site where A and B are connected; Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C40 aromatic groups, or substituted or unsubstituted C3-C40 heteroaromatic groups; Ar3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted benzophenanthryl, substituted or unsubstituted pyrene, substituted or unsubstituted fluoranyl, substituted or unsubstituted spiro[cyclohexane-1,9'-fluoren]yl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted indolocarbazolyl, substituted or unsubstituted imidazolyl, or a combination of two of the above. Ar4 is selected from substituted phenyl, substituted diphenyl, substituted terphenyl, substituted naphthyl, substituted phenanthryl, substituted benzo[phenanthryl], substituted pyrene, substituted fluoranyl, substituted spiro[cyclohexane-1,9'-fluorenyl], substituted dibenzofuranyl, substituted dibenzothiopheneyl, substituted carbazolyl, substituted benzocarbazolyl, substituted indolocarbazolyl, substituted imidazolyl, or a combination of two of the above; the substitution in Ar4 indicates that it is substituted by at least one of deuterium, halogen, cyano, isocyano, C1-C6 alkyl, deuterated C1-C6 alkyl, C3-C16 cycloalkyl, deuterated C3-C16 cycloalkyl, and deuterated C3-C16 cycloalkyl, the number of substitutions is from monosubstituted to the maximum number of substitutions, and at least one substitution indicates that it is substituted by deuterium; L is selected from single-bonded, substituted or unsubstituted C6-C40 aromatic groups, or substituted or unsubstituted C3-C40 heteroaromatic groups; m is selected from 0 or 1; When m is selected from 0, at least one of Ar1, Ar2, Ar3, and Ar4 is substituted with at least one cyano group; The substitutions in Ar1 to Ar3 and L each independently represent substitution by at least one of deuterium, halogen, cyano, isocyano, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 hydrocarbon substituted or unsubstituted C6-C30 aryl, C1-C6 hydrocarbon substituted or unsubstituted C3-C30 heteroaryl, with the number of substitutions ranging from monosubstituted to the maximum number of substitutions; The heteroatom in the heteroaryl, heteroaryl, heteroalkyl, or heterocycloalkyl group is independently selected from at least one of O, S, N, Se, Si, and Ge; The compound does not have the following structure:

2. The compound according to claim 1, characterized in that, Equation (1) is selected from the structures shown in Equations (A-1) to (A-3):

3. The compound according to claim 1, characterized in that, Equation (1) is selected from the structures shown in Equations (A-4) to (A-6):

4. The compound according to any one of claims 1-3, characterized in that, m=1, the substituents of Ar1 to Ar4 do not contain cyano groups; Alternatively, m = 0, Ar1 and / or Ar2 are substituted with at least one cyano group; Alternatively, m = 0, Ar3 and / or Ar4 are substituted with at least one cyano group.

5. The compound according to any one of claims 1-3, characterized in that, The Ar3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted benzophenanthryl, substituted or unsubstituted pyrene, substituted or unsubstituted fluoranyl, substituted or unsubstituted spiro[cyclohexane-1,9'-fluoren]yl, substituted or unsubstituted dibenzofuranyl, or a combination of two of the above. And / or, the Ar4 is selected from substituted phenyl, substituted diphenyl, substituted terphenyl, substituted naphthyl, or a combination of two of the above.

6. The compound according to any one of claims 1-3, characterized in that, Equation (1) satisfies at least one of the following conditions: (1) The Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C25 aromatic groups or substituted or unsubstituted C3-C25 heteroaromatic groups; (2) The L is selected from single-bonded, substituted or unsubstituted C6-C20 aromatic groups, or substituted or unsubstituted C3-C20 heteroaromatic groups; (3) The substitutions in Ar1 to Ar3 and L each independently represent substitution by at least one of deuterium, halogen, cyano, isocyano, C1-C4 alkyl, C3-C10 cycloalkyl, C1-C4 hydrocarbon substituted or unsubstituted C6-C20 aryl, C1-C4 hydrocarbon substituted or unsubstituted C3-C20 heteroaryl, and the number of substitutions ranges from monosubstituted to the maximum number of substitutions; (4) The substitution in Ar4 means that it is substituted by at least one of deuterium, halogen, cyano, isocyano, C1-C3 alkyl, deuterated C1-C3 alkyl, C3-C6 cycloalkyl, deuterated C3-C6 cycloalkyl, and the number of substitutions is from monosubstituted to the maximum number of substitutions, and at least one substitution means that it is substituted by deuterium.

7. The compound according to any one of claims 1-3, characterized in that, Equation (1) satisfies at least one of the following conditions: (1) Ar1 and Ar2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted fluoranyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted indolocarbazolyl, or a combination of two of the above. (2) The L is selected from single bond, phenylene, biphenylene or naphthylene; (3) The substitutions in Ar1 to Ar3 each independently represent substitution by at least one of deuterium, halogen, cyano, isocyano, methyl, ethyl, propyl, butyl, cyclopropyl, cyclohexyl, adamantyl, C1-C4 hydrocarbon substituted or unsubstituted phenyl, C1-C4 hydrocarbon substituted or unsubstituted biphenyl, C1-C4 hydrocarbon substituted or unsubstituted naphthyl, C1-C4 hydrocarbon substituted or unsubstituted pyridyl, C1-C4 hydrocarbon substituted or unsubstituted pyrimidinyl, C1-C4 hydrocarbon substituted or unsubstituted carbazolyl, the number of substitutions being from monosubstituted to the maximum number of substitutions; (4) The Ar4 is selected from substituted phenyl, substituted diphenyl, substituted triphenyl, substituted naphthyl, or a combination of two of the above; the substitution is deuterium substitution, and the number of substitutions ranges from monosubstituted to the maximum number of substitutions; or: The Ar4 is selected from substituted phenyl, substituted diphenyl, substituted terphenyl, substituted naphthyl, or a combination of two of the above; the substitution is cyano substitution and deutero substitution, the number of cyano substitutions is 1, and the number of deutero substitutions is from monosubstituted to the maximum number of substitutions.

8. The compound according to any one of claims 1-3, characterized in that, The compound is selected from one of the following structures, or one of the following structures in which hydrogen is partially or completely substituted by deuterium or fluorine:

9. An organic light-emitting device, characterized in that, It includes a cathode and an anode, the cathode being disposed opposite to the anode, and a functional layer being provided between the cathode and the anode, the functional layer comprising a compound as described in any one of claims 1-8.

10. The organic light-emitting device according to claim 9, characterized in that, The functional layer includes an electron transport layer, and the electron transport layer includes the compound.

Images