Organic compound, organic electroluminescence device, and electronic device

Abstract

The application belongs to the technical field of organic materials, and provides an organic compound, a structure of the organic compound is shown as formula 1. The application also provides an organic electroluminescent device and an electronic device containing the organic compound. The organic compound serves as an electron transport layer material, can effectively prolong the service life of the organic electroluminescent device, and improve the luminous efficiency to a certain extent.

Description

Technical Field

[0001] This application relates to the field of organic materials technology, and in particular to an organic compound, an organic electroluminescent device, and an electronic device. Background Technology

[0002] Organic electroluminescent devices, such as organic light-emitting diodes (OLEDs), typically include a cathode and an anode positioned opposite each other, and a functional layer disposed between the cathode and anode. This functional layer consists of multiple organic or inorganic film layers and generally includes an organic light-emitting layer, a hole transport layer, and an electron transport layer. When a voltage is applied to the cathode and anode, an electric field is generated between the two electrodes. Under the influence of this electric field, electrons on the cathode side move towards the electroluminescent layer, and holes on the anode side also move towards the light-emitting layer. Electrons and holes combine in the electroluminescent layer to form excitons. These excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light.

[0003] Organic electroluminescent materials are a novel flat panel display technology. The discovery of organophosphorus photoluminescence has made it possible to industrialize organic electroluminescent devices. However, the main problems with existing organic electroluminescent devices are lifespan and efficiency. As displays become larger, the driving voltage also increases, and luminous efficiency and current efficiency also need to be improved. Therefore, it is necessary to continue to develop new materials to further improve the performance of organic electroluminescent devices. Summary of the Invention

[0004] The purpose of this application is to overcome the shortcomings of the prior art and provide an organic compound and an organic electroluminescent device and electronic device containing the same, which can improve luminous efficiency and extend device life.

[0005] To achieve the above-mentioned objectives, the first aspect of this application provides an organic compound, the structure of which is shown in Formula 1:

[0006] Wherein, A and B may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, alkyl groups with 1-10 carbon atoms, or groups shown in Formula 2, and at least one of A and B is selected from groups shown in Formula 2. L1, L2, L3 and L4 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6-30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms. Each R1 may be the same or different, and each is independently selected from hydrogen, deuterium, halogen group, cyano, alkyl with 1-10 carbon atoms or aryl with 6-12 carbon atoms; n1 represents the number of R1s, and n1 is selected from 1, 2, 3, 4, 5, 6, 7 or 8. When n1 is greater than 1, any two R1s are the same or different. The substituents in L1, L2, L3, L4, A, and B may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, heteroaryl groups with 3-12 carbon atoms, aryl groups with 6-12 carbon atoms, deuterated aryl groups with 6-12 carbon atoms, haloaryl groups with 6-12 carbon atoms, alkyl groups with 1-10 carbon atoms, haloalkyl groups with 1-10 carbon atoms, or cycloalkyl groups with 3-10 carbon atoms.

[0007] A second aspect of this application provides an organic electroluminescent device, the organic electroluminescent device comprising an anode, a cathode, and at least one functional layer disposed between the anode and the cathode, the functional layer comprising the organic compound described in the first aspect of this application.

[0008] A third aspect of this application provides an electronic device, which includes the organic electroluminescent device described in the second aspect of this application.

[0009] Through the above technical solution, the organic compound of this application has a basic structure of tetramethyltetrahydronaphthalene, benzimidazole and anthracene combined; the organic compound with the above structure has high polarity and electron mobility, and is suitable for the electron transport layer of organic light-emitting electroluminescent devices; the introduction of tetramethyltetrahydronaphthalene can regulate the intermolecular forces of the organic compound with the above structure, reduce the intermolecular stacking effect and molecular crystallization ability, thereby further improving the device lifetime.

[0010] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description

[0011] The accompanying drawings, which are incorporated in and form part of this specification, illustrate embodiments consistent with this application and, together with the description, serve to explain the principles of this application.

[0012] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.

[0013] Figure 2 This is a schematic diagram of the structure of an electronic device according to one embodiment of this application.

[0014] Explanation of reference numerals in the attached figures 100, Anode; 200, Cathode; 300, Functional layer; 310, Hole injection layer; 321, Hole transport layer; 322, Electron blocking layer; 330, Organic electroluminescent layer; 350, Electron transport layer; 360, Electron injection layer; 370, Organic capping layer; 400, Electronic device.

[0015] The accompanying drawings illustrate specific embodiments of this application, which will be described in more detail below. These drawings and descriptions are not intended to limit the scope of the concept in any way, but rather to illustrate the concept of this application to those skilled in the art through reference to particular embodiments. Detailed Implementation

[0016] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, these exemplary embodiments can be implemented in many forms and should not be construed as limited to the examples set forth herein; rather, they are provided so that this application will be more comprehensive and complete, and will fully convey the concept of the exemplary embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a full understanding of embodiments of this application.

[0017] For clarity, the thickness of regions and layers may be exaggerated in the figures. The same reference numerals in the figures denote the same or similar structures, and therefore their detailed descriptions will be omitted.

[0018] The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. Numerous specific details are provided in the following description to give a thorough understanding of embodiments of this application.

[0019] The first aspect of this application provides an organic compound, the structure of which is shown in Formula 1:

[0020] Wherein, A and B may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, alkyl groups with 1-10 carbon atoms, or groups shown in Formula 2, and at least one of A and B is selected from groups shown in Formula 2. L1, L2, L3 and L4 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6-30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms. Each R1 may be the same or different, and each is independently selected from hydrogen, deuterium, halogen group, cyano, alkyl with 1-10 carbon atoms or aryl with 6-12 carbon atoms; n1 represents the number of R1s, and n1 is selected from 1, 2, 3, 4, 5, 6, 7 or 8. When n1 is greater than 1, any two R1s are the same or different. The substituents in L1, L2, L3, L4, A, and B may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, heteroaryl groups with 3-12 carbon atoms, aryl groups with 6-12 carbon atoms, deuterated aryl groups with 6-12 carbon atoms, haloaryl groups with 6-12 carbon atoms, alkyl groups with 1-10 carbon atoms, haloalkyl groups with 1-10 carbon atoms, or cycloalkyl groups with 3-10 carbon atoms.

[0021] In this application, the terms "optional" or "optionally" mean that the event or situation described below may occur but does not have to occur, and the description includes the possibility that the event or situation may or may not occur. For example, "optionally, two adjacent substituents form a ring;" means that the two substituents may form a ring but are not required to form a ring, including both scenarios where the two adjacent substituents form a ring and scenarios where the two adjacent substituents do not form a ring.

[0022] In this application, the descriptive phrases "each...independently is," "...each independently is," and "...independently selected from" are interchangeable and should be interpreted broadly. They can mean either that the specific options expressed by the same symbol in different groups do not affect each other, or that the specific options expressed by the same symbol in the same group do not affect each other. For example, " In this formula, each q is independently 0, 1, 2 or 3, and each R is independently selected from hydrogen, deuterium, fluorine or chlorine. The meaning is as follows: Formula Q-1 indicates that there are q substituents R on the benzene ring. Each R can be the same or different, and the options of each R do not affect each other. Formula Q-2 indicates that there are q substituents R on each benzene ring of biphenyl. The number q of substituents R on the two benzene rings can be the same or different, and each R can be the same or different. The options of each R do not affect each other.

[0023] In this application, a non-positioned linker bond refers to a single bond extending from the ring system. The term "" indicates that one end of the linker bond can connect to any position in the ring system that the bond penetrates, while the other end connects to the rest of the compound molecule.

[0024] For example, as shown in equation (f) below, the naphthyl group represented by equation (f) is connected to other positions in the molecule by two non-positional linkages that span the bicyclic ring, which means that any possible connection mode is shown as in equations (f-1) to (f-10).

[0025] .

[0026] For another example, as shown in equation (X'), the phenanthrene group represented by equation (X') is connected to other positions in the molecule via a non-positional linker extending from the middle of one side of the benzene ring. This means that any possible connection mode is shown in equations (X'-1) to (X'-4).

[0027] .

[0028] In this application, a non-positional substituent refers to a substituent connected by a single bond extending from the center of the ring system, indicating that the substituent can be attached to any possible position in the ring system. For example, as shown in equation (Y) below, the substituent R' represented by equation (Y) is connected to the quinoline ring by a non-positional linking bond, which means that it includes any possible connection mode shown in equations (Y-1) to (Y-7).

[0029]

[0030] .

[0031] In this application, the number of carbon atoms in R1, L1, L2, L3, L4, A, and B refers to the total number of carbon atoms. For example, if L1 is selected from a substituted arylene with 12 carbon atoms, then the total number of carbon atoms in the arylene and its substituents is 12. For example: A is... Therefore, its carbon number is 7; L1 is It has 12 carbon atoms.

[0032] In this application, unless otherwise specifically defined, "heteroatom" means a functional group comprising at least one heteroatom such as B, N, O, S, Se, Si, or P, with the remaining atoms being carbon and hydrogen. An unsubstituted alkyl group may be a "saturated alkyl group" without any double or triple bonds.

[0033] In this application, "alkyl" can include straight-chain alkyl or branched alkyl. An alkyl group can have 1 to 10 carbon atoms. In this application, numerical ranges such as "1 to 10" refer to integers within a given range; for example, "1 to 10 carbon atoms" means an alkyl group that may contain 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms. Optionally, the alkyl group is selected from alkyl groups having 1 to 5 carbon atoms, including but not limited to methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and pentyl.

[0034] In this application, cycloalkyl refers to a group derived from a saturated cyclic carbon chain structure. A cycloalkyl group may have 3 to 10 carbon atoms; in this application, numerical ranges such as "3 to 10" refer to integers within a given range; for example, "5 to 10 carbon atoms" means that it may contain 5, 6, 7, 8, 9, or 10 carbon atoms. Optionally, specific embodiments of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, norbornyl, etc.

[0035] In this application, aryl refers to any optional functional group or substituent derived from an aromatic carbon ring. An aryl group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, an aryl group can be a monocyclic aryl, a fused-ring aryl, two or more monocyclic aryl groups conjugated by carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl group conjugated by carbon-carbon bonds, or two or more fused-ring aryl groups conjugated by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups conjugated by carbon-carbon bonds can also be considered as aryl groups in this application. Fused-ring aryl groups may include, for example, bicyclic fused aryl (e.g., naphthyl), tricyclic fused aryl (e.g., phenanthrene, fluorene, anthracene), etc. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracene, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, benzo[9,10]phenanthryl, pyrene, benzofluoranthryl, phenyl, etc. The "substituted or unsubstituted aryl group" in this application may contain 6-30 carbon atoms. In some embodiments, the number of carbon atoms in the substituted or unsubstituted aryl group may be 6-25; in other embodiments, the number of carbon atoms in the substituted or unsubstituted aryl group may be 6-20; and in still other embodiments, the number of carbon atoms in the substituted or unsubstituted aryl group may be 6-18. For example, in this application, the number of carbon atoms in the substituted or unsubstituted aryl group may also be 6, 10, 12, 13, 14, 15, 18, 20, 24, 25, or 30. Of course, the number of carbon atoms may also be other numbers, which will not be listed here. In this application, biphenyl can be understood as either a phenyl-substituted aryl group or an unsubstituted aryl group.

[0036] In this application, the term "arylene" refers to a divalent group formed by the further loss of a hydrogen atom from an aryl group.

[0037] In this application, the substituted aryl group may be one or more hydrogen atoms of the aryl group that are replaced by groups such as deuterium, halogen group, cyano, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, alkoxy, alkylthio, etc.

[0038] It should be understood that the number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and its substituents. For example, a substituted aryl group with 18 carbon atoms means that the total number of carbon atoms in the aryl group and its substituents is 18.

[0039] In this application, aryl groups used as substituents include, but are not limited to, phenyl, naphthyl, anthraceneyl, phenanthryl, dimethylfluorenyl, biphenyl, etc.

[0040] In this application, the fluorene group may be substituted, and two substituents may combine with each other to form a spirostructure. Specific embodiments include, but are not limited to, the following structures: .

[0041] In this application, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5, or 6 heteroatoms, wherein the heteroatoms can be at least one of B, O, N, P, Si, Se, and S. A heteroaryl group can be a monocyclic or polycyclic heteroaryl group; in other words, a heteroaryl group can be a single aromatic ring system or a system of multiple aromatic rings conjugated by carbon-carbon bonds, and any aromatic ring system can be a single aromatic monocyclic ring or a fused aromatic ring. For example, heteroaryl groups may include thiophene, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinel, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazole, benzoxazolyl, and benzimidazole. The group includes, but is not limited to, benzothiazolyl, benzocarbazolyl, benzothiophenel, dibenzothiophenel, thienozothiophenel, benzofuranyl, phenanthrolinel, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silanyl, dibenzofuranyl, and N-arylcarbazolyl (such as N-phenylcarbazolyl), N-heteroarylcarbazolyl (such as N-pyridylcarbazolyl), and N-alkylcarbazolyl (such as N-methylcarbazolyl), etc. Among these, thiophenel, furanyl, and phenanthrolinel are heteroaryl groups of the single aromatic ring type, while N-arylcarbazolyl (such as N-phenylcarbazolyl) and N-heteroarylcarbazolyl are heteroaryl groups of the polycyclic system type linked by carbon-carbon conjugation. The "substituted or unsubstituted heteroaryl group" of this application may contain 3-30 carbon atoms. In some embodiments, the number of carbon atoms in the substituted or unsubstituted heteroaryl group may be 3-27; in other embodiments, the number of carbon atoms in the substituted or unsubstituted heteroaryl group may be 3-20; and in still other embodiments, the number of carbon atoms in the substituted or unsubstituted heteroaryl group may be 5-18. For example, the number of carbon atoms may be 3, 4, 5, 7, 12, 13, 18, or 20. Of course, the number of carbon atoms may also be other numbers, which will not be listed here.

[0042] In this application, the term "hybrid aryl" refers to a divalent group formed by the further loss of a hydrogen atom by a heteroaryl group.

[0043] In this application, the substituted heteroaryl group may be one or more hydrogen atoms of the heteroaryl group that are replaced by groups such as deuterium, halogen group, cyano, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, alkoxy, alkylthio, etc.

[0044] It should be understood that the number of carbon atoms in a substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on it.

[0045] In this application, the heteroaryl group used as a substituent includes, but is not limited to, dibenzofuranyl, dibenzothiophenyl, carbazoyl, N-phenylcarbazoyl, etc.

[0046] In this application, halogen groups may include fluorine, iodine, bromine, chlorine, etc.

[0047] In this application, a deuterated aryl group may be one or more hydrogen atoms of an aryl group that are replaced by deuterium. Specific examples of deuterated aryl groups include, but are not limited to, deuterated phenyl groups.

[0048] In this application, the halogenated aryl group can be one or more hydrogen atoms of the aryl group that are replaced by halogen atoms. Specific examples of halogenated aryl groups include, but are not limited to, fluorophenyl and chlorophenyl.

[0049] In this application, the haloalkyl group may be an alkyl group in which one or more hydrogen atoms are replaced by halogen atoms.

[0050] In some embodiments of this application, the organic compound has the structure shown in Formula 1-1 or Formula 1-2:

[0051] Wherein, A and B may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, or alkyl groups with 1-10 carbon atoms.

[0052] In some embodiments of this application, A and B may be the same or different, and are each independently selected from alkyl groups having 1-5 carbon atoms, substituted or unsubstituted aryl groups having 6-18 carbon atoms, substituted or unsubstituted heteroaryl groups having 5-18 carbon atoms, or groups represented by Formula 2, and at least one of A and B is selected from groups represented by Formula 2.

[0053] Optionally, the substituents in A and B may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, aryl groups with 6-12 carbon atoms, deuterated aryl groups with 6-12 carbon atoms, or alkyl groups with 1-5 carbon atoms.

[0054] In some embodiments of this application, A and B may be the same or different, and are each independently selected from methyl, ethyl, n-propyl, isopropyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoleyl, or a group represented by Formula 2, and at least one of A and B is selected from a group represented by Formula 2.

[0055] Optionally, the substituents in A and B may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, biphenyl or naphthyl.

[0056] In some embodiments of this application, A is selected from the group shown in Formula 2, and B is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl.

[0057] In some embodiments of this application, B is selected from the group shown in Formula 2, and A is selected from methyl, ethyl, n-propyl, isopropyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl.

[0058] In some embodiments of this application, A and B may be the same or different, and are each independently selected from methyl, ethyl, n-propyl, isopropyl, tert-butyl, the structure shown in Formula 2, or substituted or unsubstituted group V, and at least one of A and B is selected from the group shown in Formula 2; the unsubstituted group V is selected from the group consisting of:

[0059] ; in, The group V represents a chemical bond; the substituted group V contains one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, biphenyl, or naphthyl; and when the substituted group V contains multiple substituents, the substituents may be the same or different.

[0060] In some embodiments of this application, A and B may be the same or different, and are each independently selected from the group represented by Formula 2, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or the group consisting of the following groups, and at least one of A and B is selected from the group represented by Formula 2:

[0061]

[0062]

[0063] .

[0064] In some embodiments of this application, L1, L2, L3 and L4 may be the same or different, and are each independently selected from single bonds, substituted or unsubstituted aryl groups with 6-18 carbon atoms, or substituted or unsubstituted heteroaryl groups with 12-18 carbon atoms.

[0065] Optionally, the substituents in L1, L2, L3 and L4 may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, heteroaryl groups with 5-12 carbon atoms, aryl groups with 6-12 carbon atoms, deuterated aryl groups with 6-12 carbon atoms, or alkyl groups with 1-5 carbon atoms.

[0066] In some embodiments of this application, L1 and L4 may be the same or different, and are each independently selected from single bonds or phenylene oxides.

[0067] Specifically, L1 and L4 may be the same or different, and are each independently selected from the group consisting of single bonds or groups consisting of the following: .

[0068] In some embodiments of this application, L2 and L3 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiopheneylene, substituted or unsubstituted fluoreneylene, or substituted or unsubstituted carbazolylene.

[0069] Optionally, the substituents in L2 and L3 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl.

[0070] In other embodiments of this application, L2 and L3 may be the same or different, and are each independently selected from single-bonded, substituted or unsubstituted groups W, wherein the unsubstituted group W is selected from the group consisting of:

[0071] ; The substituted group W has one or more substituents, and the substituents in the substituted group W are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl, and when the number of substituents on the group W is greater than 1, the substituents are the same or different.

[0072] Optionally, L2 and L3 may be the same or different, and each may be independently selected from the group consisting of single bonds or the following groups:

[0073]

[0074]

[0075] .

[0076] In some embodiments of this application, Selected from the group consisting of single bonds or the following groups: .

[0077] Specifically, Selected from the group consisting of single bonds or the following groups:

[0078]

[0079]

[0080]

[0081] .

[0082] In some embodiments of this application, each R1 may be the same or different, and is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, or biphenyl.

[0083] In some embodiments of this application, each R1 may be the same or different, and each is independently selected from the group consisting of fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or the following groups: .

[0084] Optionally, the organic compound is selected from the group consisting of:

[0085]

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[0138] .

[0139] This application does not specifically limit the synthesis methods of the provided organic compounds. Those skilled in the art can determine suitable synthesis methods based on the organic compounds provided in the preparation examples section of this application. Those skilled in the art can obtain all the organic compounds provided in this application based on these exemplary preparation methods. All specific preparation methods for these organic compounds will not be detailed here, and should not be construed as limitations on this application.

[0140] A second aspect of this application provides an organic electroluminescent device, the organic electroluminescent device comprising an anode, a cathode, and a functional layer disposed between the cathode and the anode, the functional layer comprising the organic compound described in the first aspect of this application.

[0141] For example, such as Figure 1 As shown, the organic electroluminescent device may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 contains the organic compound provided in the first aspect of this application.

[0142] In another specific embodiment of this application, the organic electroluminescent device may be, for example, a blue organic electroluminescent device.

[0143] In another specific embodiment of this application, the functional layer includes an electron transport layer, and the electron transport layer includes the organic compound.

[0144] In one specific embodiment, the organic electroluminescent device may include an anode 100, a hole transport layer 321, an electron blocking layer 322, an organic electroluminescent layer 330 as an energy conversion layer, an electron transport layer 350, and a cathode 200 stacked sequentially.

[0145] In one specific embodiment, the anode 100 comprises the following anode materials, preferably materials with a large work function that facilitate hole injection into the functional layer. The anode materials specifically include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al and SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode comprising indium tin oxide (ITO) as the anode is also included.

[0146] In one specific embodiment, the hole transport layer 321 may include one or more hole transport materials. These materials may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds; this application does not impose any specific limitations on these materials. In one specific embodiment, the hole transport layer 321 is composed of the compound HT-1.

[0147] In one embodiment, the electron blocking layer 322 may comprise one or more materials, selected from carbazole polymers or other types of compounds, without particular limitation herein. In one embodiment, the electron blocking layer 322 is composed of the compound HT-02.

[0148] In this application, the electron transport layer 350 can be a single-layer structure or a multi-layer structure, and it can include one or more electron transport materials. The electron transport materials can also include those selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. This application does not impose any special limitations on this. In one specific embodiment, the electron transport layer 350 is composed of the compound LiQ and the organic compound of this application.

[0149] In this application, the organic electroluminescent layer 330 can be composed of a single luminescent material or of a host material and a guest material. Preferably, the organic electroluminescent layer 330 is composed of a host material and a guest material. Holes and electrons injected into the organic electroluminescent layer 330 can recombine in the organic electroluminescent layer 330 to form excitons. The excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.

[0150] The host material of the organic electroluminescent layer 330 can be a metal chelate compound, a bis(styrene) derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials. In one specific embodiment, the host material of the organic electroluminescent layer is composed of compound BH-01.

[0151] The guest material of the organic electroluminescent layer 330 can be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, and this application does not impose any special limitations on this. In one specific embodiment, the guest material is compound BD-01.

[0152] In one specific embodiment, the cathode 200 includes a cathode material that has a small work function, which facilitates electron injection into the functional layer. Specifically, examples of cathode materials include, but are not limited to: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca, but are not limited thereto. Preferably, a metal electrode containing silver and magnesium serves as the cathode.

[0153] In this application, as Figure 1 As shown, a hole injection layer 310 may also be disposed between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 may be selected from benzidine derivatives, starburst-like aryl amine compounds, phthalocyanine derivatives, or other materials, and this application does not impose any special limitations on this. In some embodiments of this application, the hole injection layer 310 may be composed of compounds HI-01 and HT-01.

[0154] In one specific implementation, such as Figure 1 As shown, an electron injection layer 360 may also be disposed between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. In one specific embodiment, the electron injection layer 360 may include ytterbium (Yb).

[0155] In one specific implementation, such asFigure 1 As shown, an organic capping layer 370 may also be provided on the cathode 200, the organic capping layer 370 including compound CP-01.

[0156] A third aspect of this application provides an electronic device, including the organic electroluminescent device provided in the second aspect of this application.

[0157] According to one implementation method, such as Figure 2 As shown, the electronic device is electronic device 400, which includes the aforementioned organic electroluminescent device. Electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as, but not limited to, computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0158] The following examples illustrate the synthesis method of the nitrogen-containing compounds of this application, but this application is not limited thereto.

[0159] Compounds synthesized using methods not mentioned in this application are all raw material products obtained through commercial means.

[0160] Synthesis of intermediate C-1

[0161] SM3 (20.00 g, 74.85 mmol) was dissolved in toluene, and Pd(pph)3Cl2 (0.69 g, 0.75 mmol), potassium acetate (14.70 g, 149.7 mmol), and pinacol diboronate (22.80 g, 89.78 mmol) were added. The reaction mixture was stirred and heated to reflux for 16 h. After the reaction mixture cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain intermediate C-1 (16.50 g, yield: 70%).

[0162] Following the synthesis method of intermediate C-1, SM4 as shown in Table 1 was used instead of SM3 to synthesize intermediate C-2 as shown in Table 1. The structures of SM4, intermediate C-2, and yields are listed in Table 1.

[0163] Table 1

[0164] Synthesis of intermediate D-2

[0165] Under nitrogen protection, SM2 (20.00 g, 101.5 mmol), intermediate C-2 (31.90 g, 101.5 mmol), tetra(triphenylphosphine)palladium (1.17 g, 1.01 mmol), anhydrous potassium carbonate (28.10 g, 203.0 mmol), tetrabutylammonium bromide (3.24 g, 10.2 mmol), toluene (160 mL), anhydrous ethanol (80 mL), and deionized water (40 mL) were added sequentially to a three-necked flask. The reaction mixture was stirred and heated to reflux for 16 h. After the reaction mixture cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain intermediate D-2 (21.00 g, yield: 68%).

[0166] Following the synthesis method of intermediate D-2, intermediate C-2 as shown in Table 2 was used instead of intermediate C-1 to synthesize intermediate D-1. The structure and yield of intermediate D-1 are listed in Table 1.

[0167] Table 2

[0168] Synthesis of intermediate A-1

[0169] SM1 (20.00 g, 59.52 mmol), SM-A-1 (11.47 g, 59.10 mmol), potassium carbonate (18.10 g, 130.1 mmol), cuprous iodide (2.3 g, 11.90 mmol), 18-crown ether-6 (0.20 g, 0.60 mmol), 1,10-phenanthroline (4.29 g, 23.8 mmol), and N,N-dimethylformamide (200 mL) were reacted for 24 h until the reaction was complete. The reaction solution was cooled to room temperature, and 500 mL of water was added. A large amount of solid precipitated out. The solid was filtered, and the filter cake was completely dissolved in 300 mL of dichloromethane. The solution was washed with water until neutral, and the organic layer was dried with anhydrous magnesium sulfate and concentrated. The crude product was purified by silica gel column chromatography (dichloromethane / n-heptane as eluent) to obtain intermediate A-1 (17.7 g, yield: 66%).

[0170] Following the synthesis method of intermediate A-1, SM-AX as shown in Table 3 was used instead of SM-A-1 to synthesize intermediate AX as shown in Table 3. The structures of SM-AX, intermediate AX, and yields are listed in Table 3.

[0171] Table 3

[0172] Synthesis of Compound 28

[0173] Under nitrogen protection, intermediates A-1 (20.00 g, 44.50 mmol), C-1 (13.40 g, 44.50 mmol), tetra(triphenylphosphine)palladium (2.6 g, 2.2 mmol), anhydrous potassium carbonate (12.3 g, 89.0 mmol), tetrabutylammonium bromide (1.43 g, 4.5 mmol), toluene (160 mL), anhydrous ethanol (80 mL), and deionized water (40 mL) were added sequentially to a three-necked flask. The reaction mixture was stirred and heated to reflux for 16 h. After the reaction mixture cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain compound 28 (18.00 g, yield: 73%).

[0174] Synthesis of compound X Referring to the synthesis of compound 28, intermediate AX was used instead of intermediate A-1 and intermediate CX was used instead of intermediate C-1 in Table 4 to synthesize compound X in the table. The structures of intermediate AX, intermediate CX, and compound X and their yields are listed in Table 4.

[0175] Table 4

[0176] Synthesis of intermediate B-1

[0177] Under nitrogen protection, A-1 (20.00 g, 44.50 mmol), F-1 (7.00 g, 44.50 mmol), tetrakis(triphenylphosphine)palladium (2.6 g, 2.2 mmol), anhydrous potassium carbonate (12.3 g, 89.0 mmol), tetrabutylammonium bromide (1.43 g, 4.5 mmol), toluene (160 mL), anhydrous ethanol (80 mL), and deionized water (40 mL) were added sequentially to a three-necked flask. The reaction mixture was stirred and heated to reflux for 16 h. After the reaction mixture cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain intermediate B-1 (14.5 g, yield: 68%).

[0178] Following the synthesis method of intermediate B-1, intermediate BX shown in Table 5 was synthesized by replacing A-1 with AX and F-1 with FX as shown in the table. The structures of AX, FX, and BX and their yields are listed in Table 5.

[0179] Table 5

[0180] Synthesis of Compound 1

[0181] Under nitrogen protection, B-1 (20.00 g, 41.50 mmol), C-1 (13.04 g, 41.5 mmol), tetrakis(triphenylphosphine)palladium (2.4 g, 2.1 mmol), anhydrous potassium carbonate (11.5 g, 83.2 mmol), tetrabutylammonium bromide (1.3 g, 4.2 mmol), toluene (160 mL), anhydrous ethanol (80 mL), and deionized water (40 mL) were added sequentially to a three-necked flask. The reaction mixture was stirred and heated to reflux for 16 h. After the reaction mixture cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain compound 1 (18.40 g, 70% yield).

[0182] Synthesis of compound Y Following the synthetic method of compound 1, compound Y was synthesized using BX instead of B-1 and CX instead of C-1 as shown in Table 6. The structures of BX, CX, and compound Y, as well as their yields, are listed in Table 6.

[0183] Table 6

[0184] Synthesis of compound 312:

[0185] D-2 (20.00 g, 65.80 mmol), E-1 (26.93 g, 65.80 mmol), potassium carbonate (19.9 g, 144.7 mmol), cuprous iodide (2.5 g, 13.2 mmol), 18-crown ether-6 (0.2 g, 0.6 mmol), 1,10-phenanthroline (4.7 g, 26.3 mmol), and N,N-dimethylformamide (200 mL) were reacted for 24 h until the reaction was complete. The reaction solution was cooled to room temperature, and 500 mL of water was added. A large amount of solid precipitated out. The mixture was filtered, and the filter cake was completely dissolved in 300 mL of dichloromethane. The solution was washed with water until neutral, and the organic layer was dried with anhydrous magnesium sulfate and concentrated. The crude product was purified by silica gel column chromatography (dichloromethane / n-heptane) to give compound 312 (28.70 g, 69%).

[0186] Synthesis of compound Z Following the synthetic method of compound 312, compound Z, shown in Table 7, was synthesized using DX instead of D-1 and EX instead of E-1. The structures of DX, EX, and compound Z, as well as their yields, are listed in Table 7.

[0187] Table 7

[0188] Mass spectrometry analysis of the synthesized compounds yielded the data shown in Table 8 below: Table 8

[0189] The NMR data for some compounds are shown in Table 9 below.

[0190] Table 9

[0191] Example 1: Fabrication of a blue organic electroluminescent device The anode is prepared by the following process: a Corning-manufactured substrate with an ITO / Ag / ITO thickness of 100Å / 1000Å / 100Å is cut into dimensions of 40mm×40mm×0.7mm. The substrate is then prepared into an experimental substrate with cathode, anode and insulating layer patterns by photolithography. The surface is treated with ultraviolet ozone and O2:N2 plasma to increase the work function of the anode (experimental substrate) and remove scum.

[0192] Compounds HI-01 and HT-01 were co-deposited at a weight ratio of 2%:98% on the anode of the experimental substrate to form a 100 Å hole injection layer. Compound HT-01 was then deposited on the hole injection layer to form a 1030 Å thick hole transport layer HTL.

[0193] Compound HT-02 was vacuum-deposited onto the hole transport layer to form an electron blocking layer with a thickness of 100 Å.

[0194] On the electron blocking layer, compounds BH-01 and BD-01 were co-deposited at a weight ratio of 97%:3% to form an organic electroluminescent layer (EML, blue luminescent layer) with a thickness of 220 Å.

[0195] On the organic electroluminescent layer, compound 1 and LiQ were deposited at a 1:1 evaporation rate to form a 310 Å thick electron transport layer.

[0196] Yb was deposited on the electron transport layer to form an electron injection layer (EIL) with a thickness of 10 Å. Then, magnesium (Mg) and silver (Ag) were vacuum deposited on the electron injection layer at a deposition rate ratio of 1:9 to form a cathode with a thickness of 120 Å.

[0197] Finally, compound CP-01 is deposited on the cathode to form an organic coating layer with a thickness of 630 Å, thereby completing the fabrication of the organic light-emitting device.

[0198] Example 2-31 The organic electroluminescent device was fabricated using the same method as in Example 1, except that, when forming the electron transport layer, the compounds shown in Table 11 below were used to replace compound 1.

[0199] Comparative Example 1 The organic electroluminescent device was fabricated using the same method as in Example 1, except that compound a, as shown in Table 10 below, was used instead of compound 1 when forming the electron transport layer.

[0200] Comparative Example 2 The organic electroluminescent device was fabricated using the same method as in Example 1, except that compound b, as shown in Table 10 below, was used instead of compound 1 when forming the electron transport layer.

[0201] Comparative Example 3 The organic electroluminescent device was fabricated using the same method as in Example 1, except that compound c, as shown in Table 10 below, was used instead of compound 1 when forming the electron transport layer.

[0202] The material structures used in the above embodiments and comparative examples are shown in Table 10 below: Table 10

[0203] The performance of the blue organic electroluminescent devices prepared in Examples 1-31 and Comparative Examples 1-3 was tested, specifically at 10 A / cm. 2The optoelectronic performance and lifetime data of the device under the specified conditions were analyzed, and the results are shown in Table 11 below.

[0204] Table 11

[0205] As shown in Table 11, Examples 1-31 using the organic compounds of this application as electron transport layer materials, compared with Comparative Examples 1-3 using known compounds as electron transport layer materials, exhibited at least a 10.4% increase in current efficiency and at least a 15.6% increase in lifetime. Therefore, when the organic compounds of this application are used to prepare organic electroluminescent devices, they can effectively reduce the device's driving voltage and also improve the device's lifetime.

Claims

1. An organic compound, characterized in that, The structure of the organic compound is shown in Formula 1: Wherein, A and B may be the same or different, and are independently selected from methyl, ethyl, n-propyl, isopropyl, tert-butyl, the structure shown in Formula 2, or substituted or unsubstituted group V, and at least one of A and B is selected from the group shown in Formula 2; the unsubstituted group V is selected from the group consisting of the following groups: ； in, The group V represents a chemical bond; the substituent group V contains one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, biphenyl, or naphthyl; and when the substituent group V contains multiple substituents, the substituents may be the same or different. L1 and L4 may be the same or different, and each is independently selected from a single bond or a phenylene group; L2 and L3 may be the same or different, and are each independently selected from single-bonded, substituted or unsubstituted groups W, wherein the unsubstituted group W is selected from the group consisting of: ； The substituted group W has one or more substituents, and the substituents in the substituted group W are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl, and when the number of substituents on the group W is greater than 1, the substituents are the same or different. Each R1 may be the same or different, and each is independently selected from hydrogen, deuterium, halogen group, cyano, alkyl with 1-10 carbon atoms or aryl with 6-12 carbon atoms; n1 represents the number of R1s, which can be selected from 1, 2, 3, 4, 5, 6, 7 or 8. When n1 is greater than 1, any two R1s are either the same or different.

2. The organic compound according to claim 1, characterized in that, The organic compound has the structure shown in Formula 1-1 or Formula 1-2:

3. The organic compound according to claim 1, characterized in that, Selected from the group consisting of single bonds or the following groups: 。 4. The organic compound according to claim 1, characterized in that, Each R1 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl.

5. The organic compound according to claim 1, characterized in that, The organic compound is selected from the group consisting of the following compounds: 。 6. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes an anode, a cathode, and at least one functional layer disposed between the anode and the cathode, the functional layer comprising an organic compound as described in any one of claims 1-5.

7. The organic electroluminescent device according to claim 6, characterized in that, The functional layer includes an electron transport layer, which includes the organic compound.

8. An electronic device, characterized in that, Including the organic electroluminescent device as described in claim 6 or 7.

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