Organic compound, and organic electroluminescent device and electronic device comprising same

By using organic compounds with specific structures, the life and efficiency problems of organic electroluminescent devices in large-area displays are solved, the charge generation efficiency and luminous efficiency are improved, and the service life of the device is extended.

CN120424094APending Publication Date: 2025-08-05SHAANXI LIGHTE OPTOELECTRONICS MATERIAL CO LTD
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Patent Information

Application Number
CN202411448209.4
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Priority Date
2024-02-04
Filing Date
2024-10-16
Publication Date
2025-08-05

AI Technical Summary

Technical Problem

Existing organic electroluminescent devices have life and efficiency problems in large-area displays, and their performance decreases as the voltage increases.

Method used

An organic compound is adopted, which has a specific structure, including a benzene ring substituted with electron withdrawing groups as the parent nucleus, connects phenanthroline or trippyridine, has multiple conjugation planes, improves the thermodynamic stability and polarity of the compound, enhances electron mobility, and improves charge generation efficiency through cooperation with metal complexes.

Benefits of technology

It improves the luminous efficiency and service life of organic electroluminescent devices and extends the service life of the device.

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Abstract

The present invention relates to an organic compound, and an organic electroluminescent device and an electronic device comprising the same. The organic compound has a structure as shown in a formula 1, and when the organic compound is applied to an organic electroluminescent device, the performance of the device can be remarkably improved. # imgabs0 #
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Description

Technical Field

[0001] The present application relates to the technical field of organic electroluminescence, and specifically, to an organic compound, an organic electroluminescent device and an electronic device comprising the same. Background Art

[0002] At present, organic electroluminescent devices are regarded as the next-generation display and lighting technologies due to advantages such as active light emission, high current efficiency, low power consumption, light weight, thinness, fast response speed, and large viewing angle. An organic electroluminescent device generally includes a cathode and an anode disposed opposite to each other, and functional layers disposed between the cathode and the anode. When a voltage is applied between the two electrodes, an electric field is generated between the two electrodes. Under the action of the electric field, electrons on the cathode side move towards the organic light-emitting layer, and holes on the anode side also move towards the organic light-emitting layer. The electrons and holes combine in the organic light-emitting layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the organic light-emitting layer to emit light externally.

[0003] Organic electroluminescent devices can have various structures, such as a single-layer structure and a stacked structure. A single-layer organic electroluminescent device only includes one light-emitting unit between the cathode and the anode, while a stacked organic electroluminescent device is formed by stacking multiple light-emitting units. A light-emitting unit generally includes at least one organic light-emitting layer, one hole-transporting layer, and one electron-transporting layer. On this basis, the light-emitting unit can further include a hole-injecting layer, an electron-injecting layer, a hole-blocking layer, and an electron-blocking layer. There is a charge generation layer (CGL) between adjacent light-emitting units for charge generation and movement. The CGL is constructed in a p-n form and includes an n-type charge generation layer (n-CGL) and a p-type charge generation layer (p-CGL). Among them, the p-type material mainly generates holes, and the n-type material is doped with a low-work-function metal through an electron-transporting layer material to generate electrons.

[0004] In existing organic electroluminescent devices, the most important problems are lifespan and efficiency. As the display area becomes larger, the voltage also increases. Therefore, it is necessary to continue to research and develop new materials to further improve the performance of organic electroluminescent devices. Summary of the Invention

[0005] In view of the above problems, an object of the present application is to provide an organic compound, an organic electroluminescent device and an electronic device comprising the same. The organic compound can be used in an organic electroluminescent device to improve the performance of the device.

[0006] A first aspect of the present application provides an organic compound having a structure shown in Formula 1:

[0007]

[0008] Among them, ET is selected from cyano, fluoro, pyridyl, cyano-substituted phenyl, cyano-substituted naphthyl, cyano-substituted biphenyl, fluoro-substituted phenyl, fluoro-substituted naphthyl or fluoro-substituted biphenyl;

[0009] Ar1 and Ar2 are the same or different, and are each independently selected from Formula 2 or Formula 3;

[0010] L1 and L2 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms;

[0011] The substituents in L1 and L2 are each independently selected from deuterium, a halogen group, cyano, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms;

[0012] R1 and R2 are the same or different, and are each independently selected from deuterium, a halogen group, cyano, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0013] The substituents in R1 and R2 are the same or different, and are each independently selected from deuterium, fluoro, cyano, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms;

[0014] m is the number of R1, m is selected from 0, 1, 2 or 3. When m is greater than 1, any two R1 are the same or different;

[0015] n is the number of R2, n is selected from 0, 1, 2, 3, 4, 5, 6 or 7. When n is greater than 1, any two R2 are the same or different.

[0016] The second aspect of the present application provides an organic electroluminescent device, including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the above-mentioned organic compound.

[0017] The third aspect of the present application provides an electronic device, including the organic electroluminescent device described in the second aspect of the present application.

[0018] The compound of the present invention uses a benzene ring substituted with an electron-withdrawing group (ET) as the mother nucleus At positions 1 and 2 of the parent nucleus, phenanthroline or terpyridine is connected. Compounds with this structure have multiple conjugated planes, high bond energy between atoms, exhibit good thermodynamic stability, and the electron-withdrawing group (ET) increases the polarity of the compound, improves the electron mobility, and is conducive to the transport of charges. At the same time, the structure provided by the present invention can effectively complex with metals. When used as a charge generation layer material, it can improve the efficiency of charge generation, thereby improving the luminous efficiency and prolonging the service life of the organic electroluminescent device.

[0019] Other features and advantages of this application will be described in detail in the subsequent detailed implementation section. Brief Description of the Drawings

[0020] The drawings are used to provide a further understanding of this application and constitute a part of the specification. Together with the following detailed implementation, they are used to explain this application, but do not constitute a limitation to this application.

[0021] Figure 1 It is a schematic structural diagram of an organic electroluminescent device according to an embodiment of this application.

[0022] Figure 2 It is a schematic structural diagram of an organic electroluminescent device according to another embodiment of this application.

[0023] Figure 3 It is a schematic structural diagram of an electronic device according to an embodiment of this application.

[0024] Description of the Reference Numerals in the Drawings

[0025] 100, Anode; 200, Cathode; 300, Functional Layer; 310, Hole Injection Layer

[0026] 321, Hole Transport Layer; 322, Electron Blocking Layer; 330, Organic Light-Emitting Layer; 340, Electron Transport Layer

[0027] 350, Electron Injection Layer 411, First Hole Transport Layer; 412, First Hole Adjustment Layer; 413, First Organic Light-Emitting Layer 414, First Electron Transport Layer; 421, n-Type Charge Generation Layer; 422, p-Type Charge Generation Layer 431, Second Hole Transport Layer; 432, Second Hole Adjustment Layer; 433, Second Organic Light-Emitting Layer 434, Second Electron Transport Layer; 410, First Light-Emitting Unit

[0028] 420, Charge Generation Layer; 430, Second Light-Emitting Unit; 500, Electronic Device Detailed Implementation

[0029] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments can be implemented in various forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this application will be more complete and comprehensive, and will fully convey the concept of the exemplary embodiments to those skilled in the art. The features, structures, or characteristics described may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of the embodiments of this application.

[0030] In a first aspect, this application provides an organic compound having the structure shown in Formula 1:

[0031]

[0032] Wherein, ET is selected from cyano, fluorine, pyridyl, cyano-substituted phenyl, cyano-substituted naphthyl, cyano-substituted biphenyl, fluorine-substituted phenyl, fluorine-substituted naphthyl or fluorine-substituted biphenyl;

[0033] Ar1 and Ar2 are the same or different and are each independently selected from Formula 2 or Formula 3;

[0034] L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0035] The substituents in L1 and L2 are each independently selected from deuterium, a halogen group, cyano, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms;

[0036] R1 and R2 are the same or different and are each independently selected from deuterium, a halogen group, cyano, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0037] The substituents in R1 and R2 are the same or different and are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms;

[0038] m is the number of R1, and m is selected from 0, 1, 2 or 3. When m is greater than 1, any two R1 are the same or different;

[0039] n is the number of R2, n is selected from 0, 1, 2, 3, 4, 5, 6 or 7, when n is greater than 1, any two R2 are the same or different.

[0040] In the present application, Ar1 and Ar2 are the same or different and are each independently selected from Formula 2 or Formula 3, that is, Ar1 is selected from Formula 2 and Ar2 is selected from Formula 3; or Ar1 is selected from Formula 3 and Ar2 is selected from Formula 2; or Ar1 is selected from Formula 2 and Ar2 is selected from Formula 2; or Ar1 is selected from Formula 3 and Ar2 is selected from Formula 3.

[0041] In this application, the descriptions “each independently selected from” and “respectively independently selected from” are interchangeable and should be understood in a broad sense. They can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or in the same group, the specific options expressed by the same symbols do not affect each other. For example, “ Wherein, each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine. The meaning is: Formula Q-1 represents that there are q substituents R" on the benzene ring, and each R" can be the same or different, and the options of each R" do not affect each other; Formula Q-2 represents that there are q substituents R" on each benzene ring of biphenyl, and the number q of R" substituents on the two benzene rings can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.

[0042] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have a substituent (hereinafter, for ease of description, the substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group or an unsubstituted aryl group having the substituent Rc. The substituent Rc can be, for example, deuterium, a halogen group, a cyano group, an alkyl group, a trialkylsilyl group, a haloalkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, etc. The number of substituents can be one or more.

[0043] In the present application, a group may be a monovalent group or a multivalent group formed by substitution.

[0044] In the present application, the number of carbon atoms in a substituted or unsubstituted functional group refers to the number of all carbon atoms.

[0045] In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. An aryl can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl. In other words, an aryl can be a monocyclic aryl, a fused polycyclic aryl, two or more monocyclic aryls connected by a carbon-carbon bond, a monocyclic aryl and a fused polycyclic aryl connected by a carbon-carbon bond, or two or more fused polycyclic aryls connected by a carbon-carbon bond. That is, unless otherwise specified, two or more aromatic groups connected by a carbon-carbon bond can also be regarded as the aryl in the present application. Among them, the fused polycyclic aryl can include, for example, bicyclic fused aryl (e.g., naphthyl), tricyclic fused aryl (e.g., phenanthryl, fluorenyl, anthryl), etc. The aryl does not contain heteroatoms such as B, N, O, S, P, Se, and Si. For example, in the present application, biphenyl, terphenyl, etc. are aryls. Examples of aryls can include, but are not limited to, phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, benzo[9,10]phenanthryl, pyrenyl, benzofluoranthenyl, yl, etc.

[0046] In the present application, the arylene involved refers to a divalent group formed by an aryl losing one more hydrogen atom.

[0047] In the present application, a substituted aryl can be one or more than one hydrogen atom in the aryl being substituted by groups such as deuterium atom, halogen group, cyano group, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, deuterated alkyl, etc. Specific examples of heteroaryl-substituted aryls can include, but are not limited to, phenyl substituted by dibenzofuranyl, phenyl substituted by dibenzothiophene, phenyl substituted by pyridine, etc. It should be understood that the number of carbon atoms of the substituted aryl refers to the total number of carbon atoms of the aryl and the substituents on the aryl. For example, a substituted aryl with 18 carbon atoms refers to the total number of carbon atoms of the aryl and the substituents being 18.

[0048] In the present application, a heteroaryl is a monovalent aromatic ring or its derivative containing at least one heteroatom in the ring, and the heteroatom can be one or more of B, O, N, P, Si, Se, and S. The heteroaryl can be a monocyclic heteroaryl or a polycyclic heteroaryl. In other words, the heteroaryl can be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds, and any aromatic ring system is an aromatic monocyclic ring or an aromatic fused ring. Exemplarily, the heteroaryl can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuryl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, silofluorene, dibenzofuryl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, etc., without being limited thereto. In the present application, the related heteroarylene is a divalent group formed by further removing one hydrogen atom from the heteroaryl.

[0049] In the present application, the substituted heteroaryl can be one or more than two hydrogen atoms in the heteroaryl being substituted by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, haloalkyl groups, deuterated alkyl groups, etc. Specific examples of the aryl-substituted heteroaryl include, but are not limited to, phenyl-substituted dibenzofuryl, phenyl-substituted dibenzothienyl, phenyl-substituted pyridyl, etc. It should be understood that the number of carbon atoms of the substituted heteroaryl refers to the total number of carbon atoms of the heteroaryl and the substituents on the heteroaryl.

[0050] In the present application, the number of carbon atoms of the aryl as a substituent can be 6 to 20. For example, the number of carbon atoms can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20. Specific examples of the aryl as a substituent include, but are not limited to, phenyl, biphenyl, naphthyl, anthryl, yl.

[0051] In the present application, the number of carbon atoms of the heteroaryl as a substituent can be 3 to 20. For example, the number of carbon atoms can be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20. Specific examples of the heteroaryl as a substituent include, but are not limited to, pyridyl, pyrimidinyl, carbazolyl, dibenzofuryl, dibenzothienyl, quinolinyl, quinazolinyl, quinoxalinyl, isoquinolinyl.

[0052] In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms of the alkyl group may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, etc.

[0053] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0054] In the present application, specific examples of the trialkylsilyl group include, but are not limited to, trimethylsilyl, triethylsilyl, etc.

[0055] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0056] In the present application, specific examples of the deuterated alkyl group include, but are not limited to, trideuteriomethyl.

[0057] In the present application, refers to a chemical bond that connects to other groups.

[0058] In the present application, the non-positioning connecting bond refers to a single bond extending from the ring system which indicates that one end of the connecting bond can be connected to any position in the ring system penetrated by the bond, and the other end is connected to the rest of the compound molecule. For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is connected to other positions of the molecule through two non-positioning connecting bonds penetrating the bicyclic ring, and the meaning it represents includes any possible connecting manner shown in formulas (f-1) to (f-10):

[0059]

[0060] For another example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is connected to other positions of the molecule through a non-positioning connecting bond extending from the middle of one side benzene ring, and the meaning it represents includes any possible connecting manner shown in formulas (X'-1) to (X'-4):

[0061]

[0062] In some embodiments of the present application, the organic compound has a structure represented by the following formula I-1, formula I-2, formula I-3, or formula I-4:

[0063]

[0064]

[0065] Among them, in Formulas 1-1 to 1-4, the definitions of ET, L1, L2, Ar1, Ar2, R1, R2, m, and n are the same as those in Formula 1. In some embodiments of the present application, selected from the group consisting of the following groups:

[0066]

[0067] In some embodiments of the present application, selected from the group consisting of the following groups:

[0068]

[0069]

[0070] In some embodiments of the present application, selected from the group consisting of the following groups:

[0071]

[0072]

[0073] In some embodiments of the present application, ET is selected from fluorine, cyano, or the group consisting of the following groups:

[0074]

[0075] In some embodiments of the present application, ET is selected from fluorine, cyano, or the group consisting of the following groups:

[0076]

[0077] In some embodiments of the present application, L1 and L2 are the same or different, and each independently selected from a single bond, a substituted or unsubstituted arylene having 6 to 16 carbon atoms, or a substituted or unsubstituted heteroarylene having 5 to 18 carbon atoms. For example, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, or 16 carbon atoms, or a substituted or unsubstituted heteroarylene having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.

[0078] Optionally, the substituents in L1 and L2 are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, or a phenyl group;

[0079] In some embodiments of the present application, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted phenanthrylene, a substituted or unsubstituted pyrenylene, a substituted or unsubstituted pyridinylene, a substituted or unsubstituted quinolinylene, a substituted or unsubstituted carbazolylene.

[0080] Optionally, the substituents in L1 and L2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteriomethyl or phenyl.

[0081] In some embodiments of the present application, L1 and L2 are the same or different and are each independently selected from a single bond or the group consisting of the following groups:

[0082]

[0083] In some embodiments of the present application, L1 and L2 are each independently selected from a single bond or the group consisting of the following groups:

[0084]

[0085] In some embodiments of the present application, each R2 is independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms.

[0086] Optionally, the substituents in R2 are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms or phenyl.

[0087] In some embodiments of the present application, each R2 is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteriomethyl, a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted anthryl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinolinyl, a substituted or unsubstituted isoquinolinyl, a substituted or unsubstituted carbazolyl.

[0088] Optionally, the substituents in R2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteriomethyl or phenyl.

[0089] In some embodiments of the present application, each R2 is independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteriomethyl or the following groups:

[0090]

[0091]

[0092] In some embodiments of the present application, each R2 is independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteriomethyl or the following groups:

[0093]

[0094] In some embodiments of the present application, each R1 is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl or trideuteriomethyl.

[0095] Specifically, the organic compound is selected from the group consisting of the following compounds:

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115] In a second aspect, the present application provides an organic electroluminescent device, including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the organic compound of the present application.

[0116] Optionally, the functional layer includes an electron transport layer, and the electron transport layer contains the organic compound of the present application.

[0117] In an embodiment of the present application, the structure of the organic electroluminescent device is as Figure 1 shown, including 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 includes a hole injection layer 310, a hole transport layer 321, an electron blocking layer 322, a light emitting layer 330, an electron transport layer 340, and an electron injection layer 350, and the electron transport layer 340 contains the organic compound of the present application.

[0118] In the present application, the anode 100 includes the following anode materials, which are preferably materials with a large work function (work function) that contribute to hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or their alloys; 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 or SnO2∶Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylenedioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but not limited thereto. Optionally, a transparent electrode including indium tin oxide (ITO) as the anode is included.

[0119] In the present application, the hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, and the present application does not make special restrictions thereon. The materials of the hole injection layer 310 are, for example, selected from the following compounds or any combination thereof:

[0120]

[0121] In one embodiment of the present application, the hole injection layer 310 is composed of HT-1 and P-dopant.

[0122] In some embodiments of the present application, the hole transporting material can be selected from triarylamine compounds or other types of compounds, and those skilled in the art can select it according to the prior art. For example, the material of the hole transporting layer is selected from the group consisting of the following compounds.

[0123]

[0124] In one embodiment of the present application, the material of the hole transporting layer 321 includes HT-1.

[0125] In one embodiment of the present application, the electron blocking layer 322 includes one or more electron blocking materials, and the electron blocking materials can be selected from carbazole polymers or other types of compounds, and the present application does not specifically limit this. For example, in some embodiments of the present application, the electron blocking layer 322 is the compound EB-1

[0126] Optionally, the organic light-emitting layer material can be composed of a single light-emitting material, or can include a host material and a guest material. Optionally, the organic light-emitting layer 330 is composed of a host material and a guest material. The holes injected into the organic light-emitting layer 330 and the electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting 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.

[0127] Optionally, the host material of the organic light-emitting layer 330 can include metal chelate compounds, bisstyryl derivatives, aromatic amine derivatives, dibenzofuran derivatives or other types of materials. The host material of the organic light-emitting layer 330 can be a single host material or a mixed host material. In one embodiment of the present application, the host material of the organic light-emitting layer 330 is BH-1

[0128] In a specific embodiment of the present application, the guest material of the organic light-emitting layer 330 is BD-1

[0129]

[0130] In the present application, the electron injection layer 350 can include inorganic materials such as alkali metal sulfides and alkali metal halides, or can include complexes of alkali metals and organic substances. In one embodiment of the present application, the electron injection layer 350 includes Yb.

[0131] Optionally, the electron transport layer 340 can be a single-layer structure or a multi-layer structure, which can include one or more electron transport materials. The electron transport materials usually can include metal complexes or / and nitrogen-containing heterocyclic derivatives. Among them, the metal complex materials can be selected from, for example, LiQ, Alq3, etc. In an embodiment of the present application, the electron transport layer 340 is composed of the compound of the present application and LiQ.

[0132] In the present application, the cathode 200 includes a cathode material, which is a material with a small work function that helps electrons to be injected into the functional layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or their alloys; or multi-layer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Optionally, a metal electrode containing magnesium and silver is included as the cathode.

[0133] In addition, the present application also provides another organic electroluminescent device as Figure 2 shown. The organic electroluminescent device includes an anode and a cathode, and a functional layer disposed between the anode and the cathode. The functional layer contains a first light-emitting unit, a second light-emitting unit, and a charge generation layer; the charge generation layer contains the organic compound of the present application. The Figure 2 organic electroluminescent device shown is also referred to as a stacked organic electroluminescent device hereinafter.

[0134] Figure 2 The stacked organic electroluminescent device shown includes an anode 100, a cathode 200, a hole injection layer 310, an electron injection layer 350, a first light-emitting unit 410, a second light-emitting unit 430, and a charge generation layer 420. The first light-emitting unit 410, the second light-emitting unit 430, and the charge generation layer 420 are located between the cathode 100 and the anode 200. The charge generation layer 420 is located between the first light-emitting unit 410 and the second light-emitting unit 430. The charge generation layer 420 contains the organic compound of the present application.

[0135] In an embodiment of the present application, the first light-emitting unit 410 includes a first hole transport layer 411, a first hole adjustment layer 412, a first organic light-emitting layer 413, and a first electron transport layer 414; the second light-emitting unit 430 includes a second hole transport layer 431, a second hole adjustment layer 432, a second organic light-emitting layer 433, and a second electron transport layer 434.

[0136] In one embodiment of the present application, the charge generation layer 420 includes an n-type charge generation layer 421 and a p-type charge generation layer 422. The n-type charge generation layer 421 provides electrons to the first electron transport layer 414 of the first light-emitting unit 410, and the p-type charge generation layer 422 provides holes to the second hole transport layer 431 of the second light-emitting unit 430. In one embodiment of the present application, the n-type charge generation layer contains the organic compound described in the present application.

[0137] In one embodiment of the present application, the n-type charge generation layer is composed of the organic compound described in the present application and a metal doping material. Optionally, the metal doping material is Li, Ca, Ag, Cs or Yb.

[0138] In one embodiment of the present application, the p-CGL layer contains HT-1 and P-dopant.

[0139] In the present application, the anode 100 includes an anode material. Optionally, the anode material includes indium tin oxide (ITO).

[0140] In one embodiment of the present application, the hole injection layer 310 is composed of HT-1 and P-dopant.

[0141] In one embodiment of the present application, the materials of the first hole transport layer 411 and the second hole transport layer 431 contain HT-1.

[0142] In one embodiment of the present application, the materials of the first hole adjustment layer 412 and the second hole adjustment layer 432 contain HT-2.

[0143] In the present application, the first organic light-emitting layer of the first light-emitting unit; and the second organic light-emitting layer of the second light-emitting unit, each may include the same or different host materials and the same or different guest materials.

[0144] In one specific embodiment of the present application, the host material of the first organic light-emitting layer 413 and the second organic light-emitting layer 433 is RH

[0145] In one specific embodiment of the present application, the guest material of the first organic light-emitting layer 413 and the second organic light-emitting layer 433 is RD

[0146] In one specific embodiment of the present application, the materials of the first electron transport layer 414 and the second electron transport layer 434 contain ET-1 and LiQ.

[0147] In one embodiment of the present application, the electron injection layer 350 contains Yb.

[0148] In a specific embodiment of the present application, the cathode 200 includes a cathode material, and the cathode material includes magnesium (Mg) and silver (Ag).

[0149] In a third aspect, the present application provides an electronic device, including the organic electroluminescent device of the second aspect of the present application.

[0150] According to one embodiment, as Figure 3 shown, the provided electronic device is the electronic device 500, which includes the above-mentioned organic electroluminescent device. The electronic device 500 can be, for example, a display device, a lighting device, an optical communication device or other types of electronic devices, and can include, for example, but not limited to, a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting lamp, an optical module, etc.

[0151] The following combines synthesis examples to specifically illustrate the synthesis method of the organic compound of the present application, but the present application is not limited thereby. The following combines synthesis examples to specifically illustrate the synthesis method of the organic compound of the present application, but the present application is not limited by any means.

[0152] Compounds for which the synthesis method is not mentioned in the present application are all raw material products obtained through commercial channels.

[0153] Synthesis Example

[0154] 1. Synthesis of Intermediate IMA-1

[0155]

[0156] Dissolve 2,9-dibromo-1,10-phenanthroline (15 g, 44.38 mmol) and phenylboronic acid (5.41 g, 44.38 mmol) in 120 mL of toluene, then add tetrakis(triphenylphosphine)palladium (0.25 g, 0.222 mmol), K2CO3 (12.24 g, 8.87 mmol), 15 mL of ethanol and 15 mL of water. Under a nitrogen atmosphere, heat to reflux for 8 h. After cooling to room temperature, extract with water and dichloromethane, dry with anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. The obtained solid was chromatographed on a column with ethyl acetate:n-heptane = 1:9 (v / v) to obtain Intermediate IMA-1 (6.4 g, yield 43%).

[0157] The intermediates IMA-X (X is 2-24) listed in Table 1 were synthesized by the same synthesis method as Intermediate IMA-1, except that raw material 1 was used instead of 2,9-dibromo-1,10-phenanthroline, and raw material 2 was used instead of phenylboronic acid. The main raw materials used, the synthesized intermediates and their yields are shown in Table 1.

[0158] Table 1

[0159]

[0160]

[0161]

[0162]

[0163] 2. Synthesis of Intermediate IM B-1

[0164]

[0165] Dissolve Intermediate IMA-1 (6 g, 17.9 mmol) and 4-chlorophenylboronic acid (2.8 g, 17.9 mmol) in 48 mL of toluene, then add tetrakis(triphenylphosphine)palladium(0) (0.1 g, 0.089 mmol), K2CO3 (4.9 g, 35.8 mmol), 6 mL of ethanol and 6 mL of water. Under a nitrogen atmosphere, heat to reflux for 6 h. After cooling to room temperature, extract with water and dichloromethane, dry with anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Recrystallize the obtained solid with dichloromethane∶n-heptane = 1∶4 (v / v) to obtain Intermediate IM B-1 (4.14 g, yield 63%).

[0166] Synthesize Intermediates IM B-X (X is 2 - 28) shown in Table 2 by the same synthesis method as Intermediate IM B-1, except that raw material 3 is used instead of IMA-1 and raw material 4 is used instead of 4-chlorophenylboronic acid. The main raw materials used, the synthesized intermediates and their yields are shown in Table 2.

[0167] Table 2

[0168]

[0169]

[0170]

[0171]

[0172]

[0173] 3. Synthesis of Intermediate IM C-X

[0174]

[0175] Intermediate IM C-1 (4 g, 10.9 mmol) and pinacol diboronate (3.32 g, 13.09 mmol) were dissolved in 40 mL of 1,4-dioxane, followed by the addition of Pd(dba2)3 (0.1 g, 0.11 mmol), X-phos (0.1 g, 0.22 mmol), and potassium acetate (1.6 g, 16.35 mmol). The mixture was heated under reflux for 5 h under a nitrogen atmosphere. After cooling to room temperature, the mixture was extracted with water and dichloromethane, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting solid was recrystallized from dichloromethane:n-heptane = 1:3 (v / v) to yield Intermediate IM C-1 (4 g, 80% yield).

[0176] The intermediates IM CX (x is 2-33) shown in Table 3 were synthesized by the same synthesis method as the intermediate IM C-1, except that the raw material 5 was used instead of the intermediate IM B-1. The main raw materials used, the synthesized intermediates and their yields are shown in Table 3.

[0177] Table 3

[0178]

[0179]

[0180]

[0181]

[0182]

[0183] Synthesis Example 1. Synthesis of Compound 5

[0184]

[0185] IMA-1 (5 g, 14.9 mmol) and intermediate IM C-2 (7.1 g, 14.9 mmol) were added to a 250 mL three-necked flask, followed by 40 mL of toluene, 5 mL of ethanol, and 5 mL of water. Tetrakis(triphenylphosphine)palladium (0.17 g, 0.149 mmol) and K2CO3 (4.1 g, 29.8 mmol) were then added. The mixture was heated to reflux for 6 h under a nitrogen atmosphere. After cooling to room temperature, 100 mL of water was added and stirred for 30 min. The mixture was filtered to solidify, and the solid was rinsed with 100 mL of ethanol, and the reaction mixture was repeated three times. The obtained solid was recrystallized from dichloromethane to obtain compound 5 (6.1 g, yield 68%). Mass spectrum (m / z) = 605.21 [M+H] + .

[0186] The compounds shown in Table 4 were synthesized using the same synthesis method as compound 5, except that raw material 6 was used instead of IMA-1, and raw material 7 was used instead of IM C-2. The main raw materials used, the synthesized compounds, their yields, and mass spectra are shown in Table 4.

[0187] Table 4

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200] NMR data of compound 5:

[0201] 1 H-NMR (CD3Cl, 400MHz): 8.36-8.28(m,8H),8.22(d,2H),8.12(d,2H),7.88(d,2H),7.80(s,4H),7.54-7.42(m,7H).

[0202] NMR data of compound 287:

[0203] 1 H-NMR(CD3Cl,400MHz):8.82(d,2H),8.72(s,2H),8.52(d,2H),8.36-8.28(m,4H), 8.13-8.06(m,2H),7.89-7.87(m,2H),7.80(s,2H),7.72(d,1H),7.58-7.42(m,7H).

[0204] Example 1: Blue Organic Electroluminescent Device

[0205] The anode was prepared through the following process: An ITO / Ag / ITO substrate with sequential thicknesses of was cut into a size of 40 mm (length) × 40 mm (width) × 0.7 mm (thickness). Using a photolithography process, it was fabricated into an experimental substrate with an anode and an insulating layer pattern. Surface treatment was carried out using ultraviolet, ozone, and O2∶N2 plasma to increase the work function of the anode, and the surface of the experimental substrate was cleaned with an organic solvent to remove impurities and oil stains on the surface of the experimental substrate.

[0206] On the experimental substrate, compound HT-1 and P-dopant were co-evaporated at an evaporation rate ratio of 98%∶2% to form a hole injection layer with a thickness of

[0207] Compound HT-1 was evaporated on the hole injection layer to form a hole transport layer with a thickness of

[0208] Compound EB-1 was evaporated on the hole transport layer to form an electron blocking layer with a thickness of

[0209] On the electron blocking layer, compound BH-1 and compound BD-1 were co-evaporated at an evaporation rate ratio of 99%∶1% to form an organic light-emitting layer with a thickness of

[0210] On the organic light-emitting layer, compound 5 and LiQ were co-evaporated at an evaporation rate ratio of 50%∶50% to form an electron transport layer with a thickness of

[0211] Yb was evaporated on the electron transport layer to form an electron injection layer with a thickness of ; then, on the electron injection layer, magnesium (Mg) and silver (Ag) were co-evaporated at an evaporation rate ratio of 10%∶90% to form a cathode with a thickness of

[0212] Finally, compound CP-1 was evaporated on the cathode to form a cathode covering layer with a thickness of thus completing the preparation of the blue organic electroluminescent device.

[0213] Examples 2 - Examples 15:

[0214] An organic electroluminescent device was prepared using the same method as in Example 1, except that in the preparation of the electron transport layer, the compound in Table 7 was used to replace compound 5 in Example 1.

[0215] ​​​​​​Comparative Example 1 - Comparative Example 2:

[0216] An organic electroluminescent device was prepared using the same method as in Example 1, except that Compound A and Compound B were used to replace Compound 5 in Example 1 when preparing the electron transport layer.

[0217] Among them, when preparing the devices of the above examples and comparative examples, the main material structures used are shown below

[0218]

[0219] The performance of the blue organic electroluminescent devices prepared in Examples 1 - 15 and Comparative Examples 1 - 2 was tested. Specifically, the IVL performance of the devices was tested under the condition of 10 mA / cm 2 The device lifetime was tested under the condition of 15 mA / cm 95 The test results are shown in Table 7 below: 2 As can be seen from Table 7 above, in Examples 1 - 15, the compounds of the present invention were used as electron transport layer materials. Compared with Comparative Examples 1 - 2, the luminous efficiency was increased by at least 11.4%, and the device lifetime was increased by at least 17.7%.

[0220] Table 7

[0221]

[0222]

[0223] To further illustrate the application of the compounds of the present application as charge generation layers in stacked organic electroluminescent devices, the performance of the materials of the present application was studied by constructing stacked devices below.

[0224] Example 16: Red stacked organic electroluminescent device

[0225] The anode was prepared through the following process: On an ITO / Ag / ITO experimental substrate with sequential thicknesses of

[0226] The surface was treated using ultraviolet, ozone, and O2∶N2 plasma to increase the work function of the anode, and the surface of the experimental substrate was cleaned using an organic solvent to remove impurities and oil stains on the surface of the experimental substrate. Compound HT - 1 and P - dopant were co - evaporated on the above experimental substrate at a vapor deposition rate ratio of 98%∶2% to form a hole injection layer with a thickness of

[0227] Compound HT - 1 was evaporated on the hole injection layer to form a layer with a thickness of

[0228] The first hole transport layer.

[0229] On the first hole transport layer, compound HT-2 is evaporated to form a first hole adjustment layer with a thickness of The first hole adjustment layer.

[0230] On the first hole adjustment layer, compound RH and compound RD are co-evaporated at a deposition rate ratio of 98%:2% to form a first organic light-emitting layer with a thickness of The first organic light-emitting layer.

[0231] On the first organic light-emitting layer, compound ET-1 and LiQ are co-evaporated at a deposition rate ratio of 50%:50% to form a first electron transport layer with a thickness of The first electron transport layer.

[0232] The above is the first light-emitting unit.

[0233] On the first electron transport layer, compound 132 and Yb are co-evaporated at a deposition rate ratio of 99%:1% to form an n-type charge generation layer with a thickness of Subsequently, on it, compound HT-1 and P-dopant are co-evaporated at a deposition rate ratio of 95%:5% to form a p-type charge generation layer with a thickness of The p-type charge generation layer.

[0234] The above is the charge generation layer.

[0235] On the p-type charge generation layer, compound HT-1 is vacuum-evaporated to form a second hole transport layer with a thickness of The second hole transport layer.

[0236] On the second hole transport layer, compound HT-2 is vacuum-evaporated to form a second hole adjustment layer with a thickness of The second hole adjustment layer.

[0237] On the second hole adjustment layer, compound RH and compound RD are co-evaporated at a deposition rate ratio of 98%:2% to form a second organic light-emitting layer with a thickness of The second organic light-emitting layer.

[0238] On the second organic light-emitting layer, compound ET-1 and LiQ are co-evaporated at a deposition rate ratio of 50%:50% to form a second electron transport layer with a thickness of The second electron transport layer.

[0239] The above is the second light-emitting unit.

[0240] Finally, Yb is evaporated on the second electron transport layer to form a thickness of an electron injection layer; then, on the electron injection layer, magnesium (Mg) and silver (Ag) are co-evaporated at an evaporation rate ratio of 10%:90% to form a cathode with a thickness of .

[0241] Finally, compound CP-1 is evaporated on the cathode to form a cathode cover layer with a thickness of , thus completing the preparation of the red stacked organic light-emitting device.

[0242] Examples 17 - Example 61:

[0243] An organic light-emitting device is prepared using the same method as in Example 16, except that in the preparation of the n-type charge generation layer, the compound in Table 8 is used to replace Compound 132 in Example 16.

[0244] Comparative Examples 3 - Comparative Example 6

[0245] An organic light-emitting device is prepared using the same method as in Example 16, except that in the preparation of the n-type charge generation layer, Compounds C, D, and E are used to replace Compound 132 in Example 16.

[0246] Among them, when preparing the devices of the above examples and comparative examples, the main material structures used in the above examples and comparative examples are shown below.

[0247]

[0248] The red stacked organic light-emitting devices prepared in Examples 16 - 61 and Comparative Examples 3 - 6 are subjected to performance tests. Specifically, the IVL performance of the devices is tested under the condition of 10 mA / cm 2 , and the device lifetime is tested under the condition of 20 mA / cm 95 . The test results are shown in Table 8 below. 2

[0249]

[0250] Table 8

[0251]

[0252] Referring to Table 8 above, in Examples 16 - 61, the compounds of the present application are used as the n-type charge generation layer material. Compared with Comparative Examples 3 - 5, the luminous efficiency is increased by at least 12.6%, and the device lifetime is increased by at least 19.2%.

[0253] Among the compounds of the present application, when the ET group contains a cyano group, it exhibits a better T95 lifetime. The reason is that the introduction of the strong electron-withdrawing cyano group can more effectively adjust the LUMO energy level of the material, making the material exhibit higher electron mobility and stronger charge generation ability, and the charge migration inside the device is more balanced, thus improving the service life of the device.

[0254] It can be seen that using the organic compound of the present application in the n-type charge generation layer of an organic electroluminescent device can significantly improve the luminous efficiency and device lifetime of the organic electroluminescent device. The preferred embodiments of the present application have been described in detail above. However, the present application is not limited to the specific details in the above embodiments. Within the scope of the technical concept of the present application, various simple modifications can be made to the technical solutions of the present application, and these simple modifications all fall within the protection scope of the present application.

Claims

1. An organic compound, characterized in that The organic compound has a structure shown in Formula 1: wherein ET is selected from cyano, fluorine, pyridyl, cyano-substituted phenyl, cyano-substituted naphthyl, cyano-substituted biphenyl, fluorine-substituted phenyl, fluorine-substituted naphthyl or fluorine-substituted biphenyl; Ar1 and Ar2 are the same or different and are each independently selected from Formula 2 or Formula 3; L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms; The substituents in L1 and L2 are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms; R1 and R2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; The substituents in R1 and R2 are the same or different and are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms; m is the number of R1, m is selected from 0, 1, 2 or 3, when m is greater than 1, any two R1 are the same or different; n is the number of R2, n is selected from 0, 1, 2, 3, 4, 5, 6 or 7, when n is greater than 1, any two R2 are the same or different.

2. The organic compound according to claim 1, wherein ET is selected from the group consisting of fluorine, cyano or the following groups:

3. The organic compound according to claim 1, wherein L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 16 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms; Optionally, the substituents in L1 and L2 are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, or a phenyl group.

4. The organic compound according to claim 1, wherein L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted quinolinylene group, or a substituted or unsubstituted carbazolylene group; Alternatively, the substituents in L1 and L2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl or phenyl.

5. The organic compound according to claim 1, wherein L1 and L2 are the same or different and are each independently selected from the group consisting of a single bond or the following groups:

6. The organic compound according to claim 1, wherein Each R2 is independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms; Optionally, the substituents in R2 are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, or a phenyl group.

7. The organic compound according to claim 1, wherein each R2 is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted carbazolyl; Optionally, the substituents in R2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl or phenyl.

8. The organic compound according to claim 1, wherein Selected from the group consisting of: Alternatively, each R2 is independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl or the following groups:

9. The organic compound according to claim 1, wherein Each R1 is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl or trideuterated methyl.

10. The organic compound according to claim 1, wherein Selected from the group consisting of:

11. The organic compound according to claim 1, wherein The organic compound is selected from the group consisting of the following compounds:

12. An organic electroluminescent device comprising an anode and a cathode, and a functional layer disposed between the anode and the cathode; characterized in that: The functional layer comprises the organic compound according to any one of claims 1 to 11; Optionally, the functional layer includes an electron transport layer, and the electron transport layer comprises the organic compound according to any one of claims 1 to 11; Optionally, the functional layer comprises a first light-emitting unit, a second light-emitting unit and a charge generation layer; the charge generation layer comprises the organic compound according to any one of claims 1 to 11.

13. An electronic device comprising the organic electroluminescent device according to claim 12.

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