Organic compound, organic electroluminescence device, and electronic device
By using an organic compound with an oxazole/thiazo[C]carbazole core structure as the host material for the organic electroluminescent layer, the problem of insufficient lifetime and efficiency of organic electroluminescent devices in large-area displays was solved, achieving high-efficiency light emission and long lifetime of the device.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- SHAANXI LIGHTE OPTOELECTRONICS MATERIAL CO LTD
- Filing Date
- 2023-05-23
- Publication Date
- 2026-05-12
AI Technical Summary
Existing organic electroluminescent devices have insufficient lifespan and efficiency in large-area displays, require high driving voltage, and need to improve luminous efficiency and current efficiency.
Organic compounds containing an oxazole/thiazolylbenzo[C]carbazole core structure are used as the host material of the organic electroluminescent layer. By connecting with aromatic amine compounds, the intermolecular forces are enhanced, the carrier mobility and electrochemical stability are improved, the carrier balance is improved, and the carrier recombination region is broadened.
It improves the luminous efficiency and lifetime of organic electroluminescent devices, and enhances the efficiency of carrier generation and utilization.
Smart Images

Figure CN117903162B_ABST
Abstract
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] The main problems with existing organic electroluminescent devices are lifespan and efficiency. As displays become larger, driving voltages also increase, and luminous efficiency and current efficiency 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, wherein the organic compound 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]
[0007] Where X and Y are each independently selected , and And there is exactly one of X and Y. The other one is or ;
[0008] R1 is selected from hydrogen, deuterium, or the structure shown in Formula 2;
[0009] R2 and R3 may be the same or different, and each is independently selected from hydrogen, deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, or the structure shown in Formula 2;
[0010] And at least one of R1, R2 and R3 has the structure shown in Equation 2;
[0011] L1, L2, L3 and L4 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.
[0012] L5 is selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms;
[0013] Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms;
[0014] The substituents in L1, L2, L3, L4, L5, Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or cycloalkyl with 3 to 10 carbon atoms;
[0015] Optionally, any two adjacent substituents in Ar1 and Ar2 can form a ring.
[0016] 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.
[0017] A third aspect of this application provides an electronic device, which includes the organic electroluminescent device described in the second aspect of this application.
[0018] Through the above technical solution, the organic compound of this application contains a core structure of oxazole / thiazo[C]carbazole, with an aromatic amine compound attached to the core, serving as the host material for the organic electroluminescent layer. On one hand, benzo[C]carbazole itself possesses a large conjugated system and a suitable first excited triplet energy level. The addition of the oxazole / thiazo[C]carbazole further increases the conjugated system, and its connection with the aromatic amine enhances intermolecular forces and improves the charge carrier mobility of the compound. On the other hand, oxazole / thiazo[C]carbazole, as an electron-deficient heterocycle, stabilizes the free radical cations formed during hole transport by the aromatic amine compound after fusion with benzo[C]carbazole, thus improving the electrochemical stability of the compound. Using the organic compound of this application as the host material for the organic electroluminescent layer can improve the charge carrier balance in the light-emitting layer, broaden the charge carrier recombination region, improve exciton generation and utilization efficiency, and enhance the luminous efficiency and lifetime of the device.
[0019] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description
[0020] 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.
[0021] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.
[0022] Figure 2 This is a schematic diagram of the structure of an electronic device according to one embodiment of this application.
[0023] Explanation of reference numerals in the attached figures
[0024] 100, Anode; 200, Cathode; 300, Functional layer; 310, Hole injection layer; 321, Hole transport layer; 322, Hole auxiliary layer; 330, Organic electroluminescent layer; 340, Electron transport layer; 350, Electron injection layer; 400, Electronic device.
[0025] 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
[0026] 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.
[0027] 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.
[0028] 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.
[0029] The first aspect of this application provides an organic compound, the structure of which is shown in Formula 1:
[0030]
[0031] Where X and Y are each independently selected , and And there is exactly one of X and Y. The other one is or ;
[0032] R1 is selected from hydrogen, deuterium, or the structure shown in Formula 2;
[0033] R2 and R3 may be the same or different, and each is independently selected from hydrogen, deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, or the structure shown in Formula 2;
[0034] And at least one of R1, R2 and R3 has the structure shown in Equation 2;
[0035] L1, L2, L3 and L4 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.
[0036] L5 is selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms;
[0037] Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms;
[0038] The substituents in L1, L2, L3, L4, L5, Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or cycloalkyl with 3 to 10 carbon atoms;
[0039] Optionally, any two adjacent substituents in Ar1 and Ar2 can form a ring.
[0040] 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.
[0041] 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.
[0042] 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.
[0043] 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).
[0044]
[0045] .
[0046] 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).
[0047] .
[0048] 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).
[0049]
[0050] .
[0051] In this application, the number of carbon atoms in L1, L2, L3, L4, L5, Ar1, Ar2, and Ar3 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, Ar1 is... Therefore, its carbon number is 7; L1 is It has 12 carbon atoms.
[0052] 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.
[0053] 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.
[0054] 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.
[0055] 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, anthraceneyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, benzo[9,10]phenanthryl, pyrene, benzofluoranthryl, phenyl, spirodifluorenyl, etc. The "substituted or unsubstituted aryl group" of this application may contain 6 to 30 carbon atoms. In some embodiments, the number of carbon atoms in the substituted or unsubstituted aryl group may be 6 to 25; in other embodiments, the number of carbon atoms in the substituted or unsubstituted aryl group may be 6 to 20; in other embodiments, the number of carbon atoms in the substituted or unsubstituted aryl group may be 6 to 18; and in other embodiments, the number of carbon atoms in the substituted or unsubstituted aryl group may be 6 to 15. For example, in this application, the number of carbon atoms in the substituted or unsubstituted aryl group can be 6, 10, 12, 13, 14, 15, 18, 20, 24, 25, or 30. Of course, the number of carbon atoms can also be other numbers, which will not be listed here. In this application, biphenyl can be understood as a phenyl-substituted aryl group or an unsubstituted aryl group.
[0056] In this application, the term "arylene" refers to a divalent group formed by the further loss of a hydrogen atom from an aryl group.
[0057] 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.
[0058] 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.
[0059] In this application, aryl groups used as substituents include, but are not limited to, phenyl, naphthyl, anthraceneyl, phenanthryl, dimethylfluorenyl, biphenyl, etc.
[0060] 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: .
[0061] 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 to 30 carbon atoms. In some embodiments, the number of carbon atoms in the substituted or unsubstituted heteroaryl group may be 3 to 27; in other embodiments, the number of carbon atoms in the substituted or unsubstituted heteroaryl group may be 12 to 24; and in still other embodiments, the number of carbon atoms in the substituted or unsubstituted heteroaryl group may be 12 to 20. 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.
[0062] 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.
[0063] 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.
[0064] 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.
[0065] In this application, the heteroaryl group used as a substituent includes, but is not limited to, dibenzofuranyl, dibenzothiophenyl, carbazoyl, N-phenylcarbazoyl, etc.
[0066] In this application, halogen groups may include fluorine, iodine, bromine, chlorine, etc.
[0067] 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, pentadeuterated phenyl.
[0068] 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.
[0069] In this application, a haloalkyl group may be an alkyl group in which one or more hydrogen atoms are replaced by halogen atoms. Specific examples of haloalkyl groups include, but are not limited to, trifluoromethyl.
[0070] In this application, terphenyl includes and .
[0071] In this application, "X and Y are each independently selected from..." , and And there is exactly one of X and Y. The other one is or "This means that one of X and Y is..." The other one is or Specifically, X is Y is Or, X is Y is Or, Y is X is Or Y is X is .
[0072] Specifically, Equation 1 has the structure shown in any one of Equations 1-1 to 1-4:
[0073]
[0074] In some embodiments of this application, the organic compound has the structure shown in Formula A, Formula B, or Formula C:
[0075]
[0076] In formulas B and C, R1 is hydrogen or deuterium.
[0077] In some specific embodiments of this application, the organic compound has a structure represented by formula AA or formula BB:
[0078]
[0079] In formula BB, R1 is hydrogen or deuterium.
[0080] In some embodiments of this application, L1, L2, L3 and L4 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 15 carbon atoms, or substituted or unsubstituted heteroaryl groups with 12 to 20 carbon atoms.
[0081] In some embodiments, L1, L2, L3, and L4 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15 carbon atoms, or substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms.
[0082] Optionally, the substituents in L1, L2, L3 and L4 may be the same or different, and each may be independently selected from deuterium, halogen groups, cyano groups, alkyl groups or phenyl groups having 1 to 5 carbon atoms.
[0083] In other embodiments of this application, L1, L2, L3 and L4 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthylene, substituted or unsubstituted fluorene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophene.
[0084] Optionally, the substituents in L1, L2, L3 and L4 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
[0085] Further optionally, L3 and L4 may be the same or different, and each is independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted biphenylene.
[0086] Further optionally, L1 and L2 may be the same or different, and each is independently selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthylene, substituted or unsubstituted fluorene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophene.
[0087] Optionally, the substituents in L1 and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
[0088] In some embodiments of this application, L1, L2, L3, and L4 may be the same or different, and each is independently selected from single-bonded, substituted, or unsubstituted groups V, wherein the unsubstituted group V is selected from the group consisting of:
[0089]
[0090] in, The substituted group V represents a chemical bond; the substituted group V contains one or more substituents selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl; and when the substituted group V contains multiple substituents, the substituents may be the same or different.
[0091] Specifically, L1 and L2 may be the same or different, and each is independently selected from the group consisting of single bonds or the following groups:
[0092]
[0093]
[0094]
[0095] .
[0096] In some embodiments of this application, L3 and L4 may be the same or different, and each is independently selected from the group consisting of single bonds or the following groups:
[0097] .
[0098] Specifically, L3 and L4 may be the same or different, and each is independently selected from the group consisting of single bonds or the following groups:
[0099] .
[0100] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms or substituted or unsubstituted heteroaryl groups having 12 to 24 carbon atoms.
[0101] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23 or 24 carbon atoms, or substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23 or 24 carbon atoms.
[0102] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and each may be independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 5 carbon atoms, aryl groups with 6 to 12 carbon atoms, or pentadeuterated phenyl groups.
[0103] Optionally, in Ar1 and Ar2, any two adjacent substituents form a fluorene ring ( ).
[0104] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted 9,9-spirodifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, or substituted or unsubstituted carbazoleyl.
[0105] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl or pentadeuterated phenyl.
[0106] Alternatively, Ar1 and Ar2 may be the same or different, and each may be independently selected from the group consisting of:
[0107]
[0108]
[0109]
[0110] .
[0111] Specifically, Ar1 and Ar2 may be the same or different, and each is independently selected from the group consisting of the following groups:
[0112]
[0113]
[0114]
[0115]
[0116]
[0117]
[0118]
[0119] .
[0120] In some embodiments of this application, and They may be the same or different, and each is independently selected from the group consisting of the following groups:
[0121]
[0122]
[0123]
[0124]
[0125] .
[0126] Specifically, and They may be the same or different, and each is independently selected from the group consisting of the following groups:
[0127]
[0128]
[0129]
[0130]
[0131]
[0132]
[0133]
[0134]
[0135]
[0136]
[0137]
[0138] .
[0139] In some embodiments of this application, L5 is selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiopheneylene, or substituted or unsubstituted fluoreneylene.
[0140] Optionally, the substituents in L5 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl.
[0141] In other embodiments of this application, L5 is selected from the group consisting of:
[0142] .
[0143] Specifically, L5 is selected from the group consisting of the following groups:
[0144]
[0145] .
[0146] In some embodiments of this application, when R1 is selected from the group shown in Formula 2, L5 is selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, or substituted or unsubstituted biphenylene.
[0147] Optionally, the substituents in L5 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl.
[0148] In other embodiments of this application, when R1 is selected from the group shown in Formula 2, L5 is selected from the group consisting of:
[0149] .
[0150] Specifically, when R1 is selected from the group shown in Formula 2, L5 is selected from the group consisting of the following groups:
[0151] .
[0152] In some specific embodiments of this application, when R1 is selected from hydrogen or deuterium, L5 is selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthyl or substituted or unsubstituted biphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene or substituted or unsubstituted fluorene.
[0153] Optionally, the substituents in L5 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl.
[0154] Optionally, when R1 is selected from hydrogen or deuterium, Selected from the group consisting of the following groups:
[0155] .
[0156] Specifically, when R1 is selected from hydrogen or deuterium, Selected from the group consisting of the following groups:
[0157]
[0158]
[0159] .
[0160] In some embodiments of this application, Selected from the group consisting of the following groups:
[0161]
[0162] .
[0163] Specifically, Selected from the group consisting of the following groups:
[0164]
[0165] .
[0166] According to some embodiments of this application, L3 is selected from the group consisting of single bonds or the following groups:
[0167] .
[0168] Specifically, L3 is selected from the group consisting of single bonds or the following groups:
[0169] .
[0170] In some embodiments of this application, Ar3 is selected from substituted or unsubstituted aryl groups having 6 to 15 carbon atoms or substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms.
[0171] Optionally, the substituents in Ar3 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, alkyl or phenyl with 1 to 5 carbon atoms.
[0172] In some embodiments of this application, Ar3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl or substituted or unsubstituted biphenyl, substituted or unsubstituted substituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl or substituted or unsubstituted carbazoleyl.
[0173] Optionally, the substituents in Ar3 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl.
[0174] In other embodiments of this application, Ar3 is selected from the group consisting of:
[0175]
[0176] .
[0177] Specifically, Ar3 is selected from the group consisting of the following groups:
[0178]
[0179] .
[0180] In this application, "at least one of R1, R2 and R3 is the structure shown in Equation 2" means that any one of R1, R2 and R3 is the structure shown in Equation 2; or any two of R1, R2 and R3 are the structure shown in Equation 2; or R1, R2 and R3 are all the structures shown in Equation 2.
[0181] In some embodiments of this application, R1 is selected from hydrogen, deuterium or the group shown in Formula 2; R2 and R3 may be the same or different, and each is independently selected from hydrogen or the group shown in Formula 2; and only one of R1, R2 and R3 is the group shown in Formula 2.
[0182] In some specific embodiments of this application, R2 and R3 are both hydrogen, and R1 has the structure shown in Formula 2.
[0183] In some specific embodiments of this application, R1 is hydrogen or deuterium, R3 is hydrogen, and R2 is the structure shown in Formula 2.
[0184] Optionally, the organic compound is selected from the group consisting of:
[0185]
[0186]
[0187]
[0188]
[0189]
[0190]
[0191]
[0192]
[0193]
[0194]
[0195]
[0196]
[0197]
[0198]
[0199]
[0200]
[0201]
[0202]
[0203]
[0204]
[0205]
[0206]
[0207]
[0208]
[0209]
[0210]
[0211]
[0212]
[0213]
[0214]
[0215]
[0216]
[0217]
[0218]
[0219]
[0220]
[0221]
[0222]
[0223]
[0224]
[0225]
[0226]
[0227]
[0228]
[0229]
[0230]
[0231]
[0232]
[0233]
[0234]
[0235]
[0236]
[0237]
[0238]
[0239]
[0240]
[0241]
[0242]
[0243]
[0244]
[0245]
[0246]
[0247] .
[0248] 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.
[0249] 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.
[0250] 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.
[0251] In another specific embodiment of this application, the organic electroluminescent device may be, for example, a red organic electroluminescent device.
[0252] In another specific embodiment of this application, the functional layer includes an organic electroluminescent layer, which includes the organic compound.
[0253] In one specific embodiment, the organic electroluminescent device may include an anode 100, a hole transport layer 321, a hole auxiliary layer 322, an organic electroluminescent layer 330 as an energy conversion layer, an electron transport layer 340, and a cathode 200, which are stacked sequentially.
[0254] 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.
[0255] In one specific embodiment, the hole transport layer 321 may include one or more hole transport materials, which may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds. In one specific embodiment, the hole transport layer 321 is composed of the organic compound HT-1.
[0256] In one specific embodiment, the hole assist layer 322 may include one or more materials, selected from carbazole polymers or other types of compounds, without specific limitation in this application. In one specific embodiment, the hole assist layer 322 is composed of the compound HT-2.
[0257] In this application, the electron transport layer 340 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 340 is composed of the compound LiQ and the compound ET.
[0258] 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.
[0259] The main 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 main material of the organic electroluminescent layer is composed of the organic compound of this application and the compound RH-N.
[0260] 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 composed of compound RD.
[0261] 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.
[0262] 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 compound PD and compound HT-1.
[0263] In one specific implementation, such as Figure 1 As shown, an electron injection layer 350 may also be disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 350. In one specific embodiment, the electron injection layer 350 may include ytterbium (Yb).
[0264] A third aspect of this application provides an electronic device, including the organic electroluminescent device provided in the second aspect of this application.
[0265] According to one implementation method, such as Figure 2As 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.
[0266] The following examples illustrate the synthesis method of the nitrogen-containing compounds of this application, but this application is not limited thereto.
[0267] Compounds synthesized using methods not mentioned in this application are all raw material products obtained through commercial means.
[0268] Synthesis of intermediate Sub-a1:
[0269]
[0270] Under nitrogen protection, IM-1 (16.21 g, 50 mmol), pinacol diborate (14.00 g, 55 mmol), potassium acetate (10.80 g, 110 mmol), and 1,4-dioxane (160 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were started, and when the system reached 40 °C, tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.46 g, 0.50 mmol) and 2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl (XPhos, 0.48 g, 1.0 mmol) were quickly added. The mixture was heated to reflux and stirred overnight. After the system cooled to room temperature, 200 mL of water was added to the system and stirred thoroughly for 30 min. The mixture was then filtered under reduced pressure. The filter cake was washed with deionized water until neutral and then rinsed with 100 mL of anhydrous ethanol to obtain a gray solid. The crude product was slurried once with n-heptane, then dissolved in 200 mL of toluene and passed through a silica gel column to remove the catalyst. After concentration, a white solid Sub-a1 (12.43 g, yield: 67%) was obtained.
[0271] Synthesis of intermediate Sub-b1:
[0272]
[0273] Under nitrogen protection, o-bromonitrobenzene (10.10 g, 50 mmol), Sub-a1 (20.42 g, 55 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (140 mL), anhydrous ethanol (35 mL), and deionized water (35 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the mixture was refluxed for 8 h. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous magnesium 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 dichloromethane / n-heptane as the mobile phase to obtain an orange-yellow solid, Sub-b1 (13.18 g, yield 72%).
[0274] Following the synthetic method of intermediate Sub-b1, intermediate Sub-bX was synthesized by replacing o-bromonitrobenzene with reactant A shown in Table 1, and the yields are listed in Table 1.
[0275] Table 1
[0276]
[0277] Synthesis of intermediate Sub-c1:
[0278]
[0279] Under nitrogen protection, Sub-b1 (18.32 g, 50 mmol), triphenylphosphine (32.78 g, 125 mmol), and o-dichlorobenzene (180 mL) were added to a 500 mL three-necked flask. Stirring and heating were initiated, and the mixture was refluxed for 24 h. After cooling to room temperature, 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 a white solid, Sub-c1 (9.70 g, 58% yield).
[0280] Following the synthesis method of intermediate Sub-c1, reactant B shown in Table 2 was used to replace Sub-b1 to synthesize intermediate Sub-cX, and the yields are listed in Table 2.
[0281] Table 2
[0282]
[0283] Synthesis of intermediate Sub-d1:
[0284]
[0285] Under nitrogen protection, Sub-c1 (16.71 g, 50 mmol), 4-chlorobromobenzene (9.57 g, 50 mmol), tris(dibenzylacetone)palladium (Pd2(dba)3, 0.916 g, 1 mmol), (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (XPhos, 0.95 g, 2 mmol), sodium tert-butoxide (9.61 g, 100 mmol), and toluene (220 mL) were added sequentially to a 500 mL three-necked flask. The mixture was heated to reflux and stirred overnight. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous magnesium 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 dichloromethane / n-heptane as the mobile phase to obtain an orange-yellow solid (18.24 g, yield: 82%).
[0286] Following the synthetic method of intermediate Sub-d1, reactant C was used instead of Sub-c1 and reactant D was used instead of 4-chlorobromobenzene as shown in Table 3 to synthesize intermediate Sub-dX. The yields are listed in Table 3.
[0287] Table 3
[0288]
[0289]
[0290]
[0291]
[0292] Synthesis of compound 15:
[0293]
[0294] Under nitrogen protection, Sub-d1 (11.12 g, 25 mmol), IM-2 (7.38 g, 25 mmol), tris(dibenzylacetone)palladium (Pd2(dba)3, 0.46 g, 0.5 mmol), (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (XPhos, 0.48 g, 1 mmol), sodium tert-butoxide (9.61 g, 50 mmol), and xylene (120 mL) were added sequentially to a 250 mL three-necked flask. The mixture was heated to reflux and stirred overnight. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous magnesium 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 dichloromethane / n-heptane as the mobile phase to obtain an orange-yellow solid (15.13 g, yield 86%, m / z = 704.27 [M+H)).+ ).
[0295] Following the synthetic method of compound 15, reactant E was used instead of Sub-d1, and reactant F was used instead of IM-2 (CAS: 897671-78-2) as shown in Table 4 to synthesize the compounds in Table 4. The yields and proton NMR data are listed in Table 4.
[0296] Table 4
[0297]
[0298]
[0299]
[0300]
[0301]
[0302]
[0303]
[0304]
[0305]
[0306]
[0307]
[0308]
[0309]
[0310] The synthesized compounds were subjected to proton nuclear magnetic resonance (NMR) spectroscopy analysis, and the data are shown in Table 5 below:
[0311] Table 5
[0312]
[0313] Example 1: Fabrication of a red organic electroluminescent device
[0314] The anode pretreatment is first carried out through the following process: On ITO / Ag / ITO substrates with thicknesses of 100Å, 1000Å and 100Å respectively, the surface is treated with ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. Alternatively, organic solvents can be used to clean the surface of the ITO substrate to remove impurities and oil stains.
[0315] On the experimental substrate (anode), PD:HT-1 was co-deposited at a deposition rate of 2%:98% to form a hole injection layer (HIL) with a thickness of 100 Å. Then, HT-1 was vacuum-deposited on the hole injection layer to form a hole transport layer with a thickness of 1065 Å. Finally, compound HT-2 was vacuum-deposited on the hole transport layer to form a hole auxiliary layer with a thickness of 890 Å.
[0316] Next, on the hole-assisted layer, compound 15:RH-N:RD was co-deposited in a ratio of 49%:49%:2% to form a red organic electroluminescent layer (EML) with a thickness of 400 Å.
[0317] On the organic electroluminescent layer, compounds ET and LiQ are co-deposited at a 1:1 evaporation rate to form a 350 Å thick electron transport layer (ETL). Yb is deposited on the electron transport layer to form a 10 Å thick electron injection layer (EIL). Then, magnesium (Mg) and silver (Ag) are mixed at a 1:9 evaporation rate and vacuum-deposited on the electron injection layer to form a 130 Å thick cathode.
[0318] Furthermore, compound CP-1 is vacuum-deposited onto the aforementioned cathode to form an organic capping layer (CPL) with a thickness of 800 Å, thereby completing the fabrication of the red organic electroluminescent device.
[0319] Examples 2-48
[0320] Except that, when preparing the organic electroluminescent layer, compound X from Table 7 was used instead of compound 15 in Example 1, the organic electroluminescent device was prepared using the same method as in Example 1.
[0321] Comparative Examples 1-3
[0322] Except that, when preparing the organic electroluminescent layer, compound A, compound B, and compound C were used to replace compound 15 in Example 1, the organic electroluminescent device was prepared using the same method as in Example 1.
[0323] The material structures used in the above embodiments and comparative examples are shown in Table 6 below:
[0324] Table 6
[0325]
[0326] The performance of the red organic electroluminescent devices prepared in Examples 1-48 and Comparative Examples 1-3 was tested, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the specified conditions. The lifetime of the T95 device was 20 mA / cm. 2 The test was conducted under the specified conditions, and the test results are shown in Table 7.
[0327] Table 7
[0328]
[0329]
[0330] Referring to Table 7 above, when the compounds of this application are used as the host material for red organic electroluminescent devices, the current efficiency is increased by at least 11.8%, and the lifetime is increased by at least 12.2%. The reason for this is that the organic compound structure of this application contains a core structure of oxazole / thiazolyl-benzo[C]carbazole, with an aromatic amine compound attached to the core, serving as the host material for the organic electroluminescent layer. On the one hand, benzo[C]carbazole itself has a large conjugated system and a suitable first excited triplet energy level, and the addition of the oxazole / thiazolyl ring can further increase the conjugated system. Attaching it to the aromatic amine enhances intermolecular forces and improves the carrier mobility of the compound. On the other hand, oxazole / thiazolyl, as an electron-deficient heterocycle, when fused with benzo[C]carbazole, can stabilize the free radical cations formed by the aromatic amine compound during hole transport, thus improving the electrochemical stability of the compound. When the compound of this application is used as a hole transport material in a hybrid host material, it can improve the carrier balance in the light-emitting layer, broaden the carrier recombination region, improve exciton generation and utilization efficiency, and improve the device luminescence efficiency and lifetime.
Claims
1. An organic compound, characterized in that, The structure of the organic compound is shown in Formula 1: Formula 1 Formula 2 Where X and Y are each independently selected , And there is exactly one of X and Y. The other one is ; R1 is selected from hydrogen, deuterium, or the structure shown in Formula 2; R2 and R3 may be the same or different, and each is independently selected from hydrogen, deuterium or the structure shown in Formula 2; And at least one of R1, R2 and R3 has the structure shown in Equation 2; L1 and L2 may be the same or different, and each is independently selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranylene or substituted or unsubstituted dibenzothiopheneylene. L3 is selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, or substituted or unsubstituted phenanthrene; L4 is selected from a single bond; The substituents in L1, L2, and L3 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl. L5 is selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiopheneylene, or substituted or unsubstituted fluoreneylene. The substituents in L5 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl; Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted 9,9'-spirodifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl or substituted or unsubstituted carbazolyl; The substituents in Ar1 and Ar2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl or pentadeuterated phenyl; Ar3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted biphenyl; The substituents in Ar3 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl.
2. The organic compound according to claim 1, characterized in that, The organic compound has a structure as shown in formula AA or formula BB: In formula BB, R1 is hydrogen or deuterium.
3. The organic compound according to claim 1, characterized in that, and They may be the same or different, and each is independently selected from the group consisting of the following groups: 。 4. The organic compound according to claim 1, characterized in that, Selected from the group consisting of the following groups: ; L3 is selected from the group consisting of single bonds or the following groups: 。 5. The organic compound according to claim 1, characterized in that, Ar3 is selected from the group consisting of the following groups: 。 6. The organic compound according to claim 1, characterized in that, R1 is selected from hydrogen, deuterium, or the structure shown in Formula 2; R2 and R3 may be the same or different, and each is independently selected from hydrogen or the structure shown in Formula 2; Furthermore, there is exactly one of R1, R2, and R3 that has the structure shown in Equation 2.
7. An organic compound, characterized in that, The organic compound is selected from the group consisting of the following compounds: 。 8. 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 to 7.
9. The organic electroluminescent device according to claim 8, characterized in that, The functional layer includes an organic electroluminescent layer, which includes the organic compound.
10. An electronic device, characterized in that, Including the organic electroluminescent device as described in claim 8 or 9.