Organic compounds, organic electroluminescent devices, and electronic devices

Abstract

The application relates to the technical field of organic electroluminescent materials, and provides an organic compound, an organic electroluminescent device and an electronic device. The organic compound has a structure shown in formula I. The organic compound shown in formula I is applied to the organic electroluminescent device, and the performance of the device can be remarkably improved.

Description

Technical Field

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

[0002] Organic light-emitting devices, also known as organic light-emitting diodes (OLEDs), have advantages such as fast response speed, low driving voltage, and the ability to achieve wide color gamut display.

[0003] Organic light-emitting diodes (OLEDs) typically consist of an anode, a cathode, and a functional layer formed between these two electrodes. This functional layer can include hole injection layers, hole transport layers, hole auxiliary layers, electron blocking layers, organic light-emitting layers, hole blocking layers, electron transport layers, and electron injection layers. Among these, the organic light-emitting layer is the core light-emitting functional layer of the OLED device. Through the synergistic effect of the organic host material and the light-emitting dopant, it achieves carrier recombination and efficient electroluminescence, determining the device's chromaticity, efficiency, lifetime, and display quality.

[0004] Boron-nitrogen resonance structures are a class of dopants that have attracted much attention in recent years. They have atomically separated highest occupied molecular orbitals (HOMO) and lowest unoccupied molecular orbitals (LUMO), which allows them to undergo charge transfer (CT) during electronic transitions, thereby improving exciton utilization and increasing the quantum yield of light emission.

[0005] Therefore, it is essential to develop a boron-nitrogen resonance material with high stability and high luminescence efficiency. Summary of the Invention

[0006] To address the aforementioned issues, this application provides an organic compound, an organic electroluminescent device, and an electronic device. The organic compound, when used in the organic electroluminescent device, can improve the device's luminous efficiency and lifespan.

[0007] In a first aspect, this application provides an organic compound having the structure shown in Formula I:

[0008] In this case, one of ring A and ring B is selected from the structure shown in Formula II, and the other is selected from a substituted or unsubstituted aromatic ring with 6 to 40 carbon atoms or a substituted or unsubstituted heteroaromatic ring with 12 to 40 carbon atoms. "*" indicates the fusion site between the structure shown in Formula II and the structure shown in Formula I. Any three adjacent fusion sites in Formula II are fused with Formula I. The substituents in ring A and ring B may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, deuterated trialkylsilyl with 3 to 12 carbon atoms, aryl with 6 to 30 carbon atoms, deuterated aryl with 6 to 30 carbon atoms, heteroaryl with 3 to 30 carbon atoms, deuterated heteroaryl with 3 to 30 carbon atoms, arylamine with 12 to 20 carbon atoms, or deuterated arylamine with 12 to 20 carbon atoms; X1 and X2 may be the same or different, and each is independently selected from single bonds, O, S, C(R) bonds. a R b ) or N(R c ); R a R b and R c They may be the same or different, and each independently selected from alkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 18 carbon atoms, deuterated aryl groups having 6 to 18 carbon atoms, haloaryl groups having 6 to 18 carbon atoms, aryl groups substituted with alkyl or deuterated alkyl groups having 1 to 5 carbon atoms, or deuterated aryl groups substituted with alkyl or deuterated alkyl groups having 1 to 5 carbon atoms; Optional, R a and R b The carbon atoms that are connected to each other form a ring W, wherein the ring W is selected from cycloalkanes with 3 to 8 carbon atoms or aromatic rings with 6 to 13 carbon atoms; Rings C, D, E, and F may be the same or different, and each is independently selected from aromatic rings with 6 to 30 carbon atoms or heteroaromatic rings with 3 to 30 carbon atoms; R1, R2, R3, R4, R5, R6, R7, R8, and R9 may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, deuterated trialkylsilyl with 3 to 12 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms, or substituted or unsubstituted aromatic amino with 12 to 20 carbon atoms; The substituents in R1, R2, R3, R4, R5, R6, R7, R8, and R9 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or deuterated heteroaryl with 3 to 20 carbon atoms; n1 represents the number of substituents R1, which is selected from 0, 1, 2 or 3. When n1 is greater than 1, each R1 may be the same or different. Optionally, any two adjacent R1s are connected to form a substituted or unsubstituted 6- to 15-membered ring X. n2 represents the number of substituents R2, which is selected from 0, 1, 2, 3 or 4. When n2 is greater than 1, each R2 may be the same or different. Optionally, any two adjacent R2s are connected to form a substituted or unsubstituted 6- to 15-membered ring Y. n3 represents the number of substituents R3, which is selected from 0, 1 or 2. When n3 is 2, each R3 may be the same or different. Optionally, any two adjacent R3s are connected to form a substituted or unsubstituted 6- to 15-membered ring Z. n4 represents the number of substituents R4, which is selected from 0 to the maximum number of substitutable elements. When n4 is greater than 1, each R4 may be the same or different. n5 represents the number of substituents R5, which is selected from 0 to the maximum number of substitutable elements. When n5 is greater than 1, each R5 may be the same or different. n6 represents the number of substituents R6, and n6 is selected from 0 or 1; n7 represents the number of substituents R7, which can be selected from 0, 1, 2, 3 or 4. When n7 is greater than 1, the R7s may be the same or different. n8 represents the number of substituents R8, which is selected from 0 to the maximum number of substitutable elements. When n8 is greater than 1, each R8 may be the same or different. n9 represents the number of substituents R9, which is selected from 0 to the maximum number of substitutable elements. When n9 is greater than 1, each R9 may be the same or different. The substituents in ring X, ring Y, and ring Z may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, trimethylsilyl, deuterated trimethylsilyl, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, heteroaryl with 3 to 12 carbon atoms, deuterated heteroaryl with 3 to 12 carbon atoms, aromatic amino with 12 to 20 carbon atoms, or deuterated aromatic amino with 12 to 20 carbon atoms.

[0009] In a second aspect, this 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 first aspect.

[0010] Thirdly, this application provides an electronic device including the organic electroluminescent device of the second aspect.

[0011] The compound structure of this application is a resonant organic light-emitting material containing a double spirofluorene boron nitrogen structure.

[0012] Spirofluorene is a good electron-donating and steric hindrance group. Introducing two spirofluorenes on the same side of the BN resonance structure—that is, replacing carbazole with spirofluorene-carbazole on the basis of a single spirofluorene boron-nitrogen material—with the two spirofluorenes connected or fused to the same carbazole, can enhance the rigidity of the molecular skeleton while forming a larger molecular conjugated plane, effectively reducing the impact of the large conjugated plane on molecular stability, improving the thermal and chemical stability of the molecule, and thus improving the lifetime of OLED devices. Simultaneously, placing the two spirofluorenes on the same side allows for the control of the size of the molecular conjugated plane, increasing the intermolecular distance of the luminescent material, suppressing strong π-π interactions between molecules, effectively preventing intermolecular stacking, and improving molecular luminescence efficiency. In summary, the compound of this application can achieve simultaneous improvement in core indicators such as efficiency and lifetime of OLED devices. Attached Figure Description

[0013] The accompanying drawings are provided to further understand this application and form part of the specification. They are used together with the following detailed description to explain this application, but do not constitute a limitation thereof.

[0014] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application; Figure 2 This is a schematic diagram of the structure of an electronic device according to one embodiment of this application.

[0015] Explanation of reference numerals in the attached figures: 100 - Anode; 200 - Cathode; 300 - Functional layer; 310 - Hole injection layer; 320 - Hole transport layer; 321 - First hole transport layer; 322 - Second hole transport layer; 330 - Organic light-emitting layer; 340 - Hole blocking layer; 350 - Electron transport layer; 360 - Electron injection layer; 400 - Electronic device. Detailed Implementation

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

[0017] In this application, the terms "optionally" or "optionally" mean that the events or circumstances described below may or may not occur. For example, "optionally, any two adjacent R2 groups may connect to form a ring" includes: a scenario where any two adjacent substituents R2 form a ring, and a scenario where any two adjacent substituents R2 exist independently without forming a ring. "Any two adjacent" can include having two substituents on the same atom, or having one substituent on each of two adjacent atoms; wherein, when there are two substituents on the same atom, the two substituents may form a saturated or unsaturated spirocyclic ring with the atom they are connected to; when there is one substituent on each of two adjacent atoms, the two substituents may fuse to form a ring.

[0018] In this application, the terms "optionally", "preferredly", and "in some embodiments" have the same meaning.

[0019] In this application, a ring system consisting of n atoms is called an n-membered ring. When the ring is substituted by a substituent, the number of atoms contained in the substituent is not included in "n". For example, a substituted or unsubstituted phenyl group is a 6-membered aryl group, a substituted or unsubstituted naphthalene ring is a 10-membered aryl ring, and a substituted or unsubstituted benzofuran ring is a 9-membered ring. These are not listed here.

[0020] In this application, the descriptive phrases "each...independently is," "...each independently is," and "...each independently is" 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 the formula Q-1, 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 of substituents q 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.

[0021] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have substituents. For example, "substituted or unsubstituted aryl" refers to an aryl group with substituents or an aryl group without substituents. The substituents mentioned above can be, for example, deuterium, fluorine, cyano, heteroaryl, aryl, deuterated aryl, trialkylsilyl, alkyl, haloalkyl, deuterated alkyl, cycloalkyl, etc. The number of substituents can be one or more.

[0022] In this application, "multiple" means two or more, such as two, three, four, five, six, etc.

[0023] In this application, the number of carbon atoms in a substituted or unsubstituted functional group refers to the total number of carbon atoms in that group, including the substituents. For example, if L1 is a substituted arylene with 12 carbon atoms, then the total number of carbon atoms in the arylene and its substituents is 12.

[0024] The hydrogen atoms in the compound structure of this application include various isotopes of hydrogen, such as hydrogen (H), deuterium (D), or tritium (T).

[0025] 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 linked by carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl linked by carbon-carbon bonds, or two or more fused-ring aryl groups linked by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups linked 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 include, but are not limited to, phenyl, naphthyl, fluorenyl, spirodifluorenyl, anthracene, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, triphenylene, perylene, benzo[9,10]phenanthryl, pyrene, benzofluoranthryl, phenylene, etc. Furthermore, alicyclic aromatic hydrocarbons are also classified as aryl in this application, such as substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydroanthryl, substituted or unsubstituted indenyl, substituted or unsubstituted acenaphthene, etc., which are also within the scope of aryl groups described in this application.

[0026] In this application, the substituted aryl group can be one or more hydrogen atoms of the aryl group that are substituted by groups such as deuterium, halogen groups, cyano, aryl, deuterated aryl, heteroaryl, trialkylsilyl, alkyl, haloalkyl, deuterated alkyl, etc. Specific examples of heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl, dibenzothiophene-substituted phenyl, pyridine-substituted phenyl, etc. It should be understood that the number of carbon atoms in the substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group. For example, a substituted aryl group with 18 carbon atoms means that the total number of carbon atoms of the aryl group and the substituents is 18.

[0027] In this application, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5, or 6 heteroatoms. The heteroatoms can be one or more of B, O, N, P, Si, Se, and S. A heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, a heteroaryl group can be a single aromatic ring system or a system of multiple aromatic rings linked by carbon-carbon bonds, and any aromatic ring system can be an aromatic monocyclic ring or an aromatic fused ring. For example, heteroaryl groups may include thiopheneyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolinyl, indolyl, carbazoleyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazoleyl, benzothiaphenyl, dibenzothiaphenyl, thiaphenothiaphenyl, benzofuranyl, phenanthrololinyl, isoxazolyl, thiadiazolyl, phenthiaazinyl, silfluorenyl, dibenzofuranyl, and N -Phenylacetazolyl, N -pyridylcarbazole group, N- Methylcarbazolyl, etc., but not limited to these.

[0028] In this application, the substituted heteroaryl group can be one or more hydrogen atoms of the heteroaryl group that are replaced by groups such as deuterium, halogen groups, cyano, aryl, heteroaryl, trialkylsilyl, alkyl, haloalkyl, deuteryl, triphenylsilyl, etc. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothiophenyl, phenyl-substituted pyridyl, etc. It should be understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group.

[0029] In this application, deuterated aryl refers to an aryl group containing at least one deuterated substituent. Specific embodiments of deuterated aryl include, but are not limited to, pentadeuterated phenyl, pentadeuterated biphenyl, or nonadeuterated biphenyl.

[0030] In this application, the number of carbon atoms in the substituted or unsubstituted aryl group can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; in some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; in still other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; in still other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms; in still other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms; and in some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0031] In this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl group can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40. In some embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 3 to 40; in some embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 12 to 40; in still other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 3 to 30; in yet another embodiment, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 3 to 20; in yet another embodiment, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 3 to 18; and in yet another embodiment, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 3 to 12.

[0032] In this application, substituted or unsubstituted aromatic amino groups include at least one aryl group attached to an amino group with an N atom, such as one or two aryl groups attached to the N atom, including but not limited to diphenylamine.

[0033] In this application, the number of carbon atoms of the aryl group 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 or 20. Specific examples of the aryl group as a substituent include, but are not limited to, phenyl, biphenyl, naphthyl, anthracene, hydroxyl or tetrahydronaphthyl.

[0034] In this application, the number of carbon atoms in the heteroaryl group used 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 or 20. Specific examples of heteroaryl groups used as substituents include, but are not limited to, pyridinyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, quinolinyl, quinazolinyl, quinoxalinyl or isoquinolinyl.

[0035] In this application, terphenyl includes and .

[0036] In this application, the fluorene group can be substituted by one or more substituents. When the fluorene group is substituted, the substituted fluorene group can be: , , , etc., but not limited to this.

[0037] In this application, spirofluorene includes a spiro-ring structure formed by the mutual fusion of two fluorene rings and a spiro-ring conjugated structure formed by the helical bridging and bonding of a single fluorene ring with other aromatic rings or heterocycles. For example, a spirofluorene can be: , , Z can be O, S, C(R) d R e ) or N(R f ); R d R e and R f Whether the groups are the same or different, they are each independently selected from alkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 18 carbon atoms, deuterated aryl groups having 6 to 18 carbon atoms, haloaryl groups having 6 to 18 carbon atoms, aryl groups substituted with alkyl or deuterated alkyl groups having 1 to 5 carbon atoms, or deuterated aryl groups substituted with alkyl or deuterated alkyl groups having 1 to 5 carbon atoms.

[0038] In this application, the number of carbon atoms in alkyl groups having 1 to 10 carbon atoms can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of alkyl groups 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.

[0039] In this application, the halogen group can be fluorine, chlorine, bromine or iodine.

[0040] In this application, halogenated alkyl refers to halogen-substituted alkyl groups.

[0041] In this application, deuterated alkyl means one or more deuterated alkyl groups.

[0042] In this application, the number of carbon atoms in the deuterated alkyl group with 1 to 10 carbon atoms can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, and specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl.

[0043] In this application, the number of carbon atoms in the alkyl halogroup is, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of alkyl halogroups include, but are not limited to, trifluoromethyl.

[0044] In this application, the number of carbon atoms in a trialkylsilyl group with 3 to 12 carbon atoms can be, for example, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12, and specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl groups.

[0045] In this application, It refers to the chemical bond that connects with other groups.

[0046] In this application, the single bond extending from the loop system involved in the non-positioning link is not specified. The term "" indicates that one end of the linker can connect to any position in the ring system it traverses, while the other end connects to the rest of the compound molecule. For example, as shown in equation (f), the naphthyl group represented by equation (f) is connected to other positions in the molecule via two non-positional linkers that traverse the bicyclic ring. This means that any possible connection configuration shown in equations (f-1) to (f-10) is acceptable.

[0047] .

[0048] For another example, as shown in equation (X'), the dibenzofuran 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 shown in equations (X'-1) to (X'-4) is included. .

[0049] 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):

[0050]

[0051] In a first aspect, this application provides an organic compound having the structure shown in Formula I:

[0052] In this case, one of ring A and ring B is selected from the structure shown in Formula II, and the other is selected from a substituted or unsubstituted aromatic ring with 6 to 40 carbon atoms or a substituted or unsubstituted heteroaromatic ring with 12 to 40 carbon atoms. "*" indicates the fusion site between the structure shown in Formula II and the structure shown in Formula I. Any three adjacent fusion sites in Formula II are fused with Formula I. The substituents in ring A and ring B may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, deuterated trialkylsilyl with 3 to 12 carbon atoms, aryl with 6 to 30 carbon atoms, deuterated aryl with 6 to 30 carbon atoms, heteroaryl with 3 to 30 carbon atoms, deuterated heteroaryl with 3 to 30 carbon atoms, arylamine with 12 to 20 carbon atoms, or deuterated arylamine with 12 to 20 carbon atoms; X1 and X2 may be the same or different, and each is independently selected from single bonds, O, S, C(R) bonds. a R b ) or N(R c ); R a R b and R c They may be the same or different, and each independently selected from alkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 18 carbon atoms, deuterated aryl groups having 6 to 18 carbon atoms, haloaryl groups having 6 to 18 carbon atoms, aryl groups substituted with alkyl or deuterated alkyl groups having 1 to 5 carbon atoms, or deuterated aryl groups substituted with alkyl or deuterated alkyl groups having 1 to 5 carbon atoms; Optional, R a and R bThe carbon atoms that are interconnected with each other form a ring W, wherein the ring W is selected from cycloalkanes having 3 to 8 carbon atoms or aromatic rings having 6 to 13 carbon atoms; for example, the ring W can be a fluorene ring or cyclohexane; Rings C, D, E, and F may be the same or different, and each is independently selected from aromatic rings with 6 to 30 carbon atoms or heteroaromatic rings with 3 to 30 carbon atoms; R1, R2, R3, R4, R5, R6, R7, R8, and R9 may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, deuterated trialkylsilyl with 3 to 12 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms, or substituted or unsubstituted aromatic amino with 12 to 20 carbon atoms; The substituents in R1, R2, R3, R4, R5, R6, R7, R8, and R9 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or deuterated heteroaryl with 3 to 20 carbon atoms; n1 represents the number of substituents R1, which is selected from 0, 1, 2 or 3. When n1 is greater than 1, each R1 may be the same or different. Optionally, any two adjacent R1s are connected to form a substituted or unsubstituted 6- to 15-membered ring X. n2 represents the number of substituents R2, which is selected from 0, 1, 2, 3 or 4. When n2 is greater than 1, each R2 may be the same or different. Optionally, any two adjacent R2s are connected to form a substituted or unsubstituted 6- to 15-membered ring Y. n3 represents the number of substituents R3, which is selected from 0, 1 or 2. When n3 is 2, each R3 may be the same or different. Optionally, any two adjacent R3s are connected to form a substituted or unsubstituted 6- to 15-membered ring Z. n4 represents the number of substituents R4, which is selected from 0 to the maximum number of substitutable elements. When n4 is greater than 1, each R4 may be the same or different. n5 represents the number of substituents R5, which is selected from 0 to the maximum number of substitutable elements. When n5 is greater than 1, each R5 may be the same or different. n6 represents the number of substituents R6, and n6 is selected from 0 or 1; n7 represents the number of substituents R7, which can be selected from 0, 1, 2, 3 or 4. When n7 is greater than 1, the R7s may be the same or different. n8 represents the number of substituents R8, which is selected from 0 to the maximum number of substitutable elements. When n8 is greater than 1, each R8 may be the same or different. n9 represents the number of substituents R9, which is selected from 0 to the maximum number of substitutable elements. When n9 is greater than 1, each R9 may be the same or different. The substituents in ring X, ring Y, and ring Z may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, trimethylsilyl, deuterated trimethylsilyl, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, heteroaryl with 3 to 12 carbon atoms, deuterated heteroaryl with 3 to 12 carbon atoms, aromatic amino with 12 to 20 carbon atoms, or deuterated aromatic amino with 12 to 20 carbon atoms.

[0053] In some embodiments of this application, the organic compound is selected from the structures shown in formulas I-1 to I-8:

[0054] In Equations I-1 to I-8, the definitions of R1 to R9 and n1 to n9 are the same as the definitions of R1 to R9 in the structure shown in Equation I, and will not be repeated here.

[0055] When ring A has the structure shown in Formula II, Formula I has the structure shown in one of Formulas I-1 to I-4; when ring B has the structure shown in Formula II, Formula I has the structure shown in one of Formulas I-5 to I-8.

[0056] In some embodiments of this application, one of ring A and ring B has the structure shown in Formula II, and the other is selected from substituted or unsubstituted benzene rings. ), substituted or unsubstituted naphthalene rings ( ), substituted or unsubstituted anthracene rings ( ), substituted or unsubstituted phenanthrene rings ( , ), substituted or unsubstituted tetrahydronaphthalene ring ( ), substituted or unsubstituted fluorene rings ( , ), replaced or unreplaced spirofluorene rings ( , ), substituted or unsubstituted dibenzofuran ring ( , ), substituted or unsubstituted dibenzothiophene ring ( , ), substituted or unsubstituted biphenyl rings ( ), substituted or unsubstituted phenyl dibenzothiophene ring ( ), substituted or unsubstituted phenyl dibenzofuran ring ( ), or, substituted or unsubstituted phenylcarbazole ring ( ); The substituents in ring A or ring B may be one or more. When there are multiple substituents in ring A or ring B, each substituent may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, trimethylsilyl, deuterated trimethylsilyl, aryl with 6 to 18 carbon atoms, deuterated aryl with 6 to 18 carbon atoms, heteroaryl with 3 to 18 carbon atoms, deuterated heteroaryl with 3 to 18 carbon atoms, substituted or unsubstituted diphenylamino, or substituted or unsubstituted deuterated diphenylamino. As a non-limiting example, the substituents in ring A or ring B are one or more, and when there are multiple substituents in ring A or ring B, the substituents may be the same or different, and each is independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, trimethylsilyl, deuterated trimethylsilyl, or the group consisting of deuterated or undeuterated groups: .

[0057] In some embodiments of this application, one of ring A or ring B is selected from the structure shown in Formula II, and the other is selected from the group consisting of deuterated or undeuterated groups: .

[0058] In some embodiments of this application, rings C, D, E, and F may be the same or different, and each is independently selected from benzene rings ( ), naphthalene ring ( , , ), Philippine Ring ( ), anthracene ( , ), benzofuran ring ( , , ), dibenzofuran ring ( , , ), benzothiophene ring ( , , ), dibenzothiophene ring ( , , ) N -Phenyl indole ring ( , , ), N -Phenylacetazole ring ( , , ), indene ring ( , , ), fluorene ring ( , , ), pyridine ring ( ), pyrimidine ring ( ), benzopyridine ring ( ), benzopyrimidine ring ( ), naphthopyridine ring ( , ) or naphthopyrimidine ring ( , ), * indicates the fusion sites of rings C, D, E, and F with adjacent rings.

[0059] In some embodiments of this application, formula II is selected from one of the following structures: ; The definitions of R6, R7, R8, and R9 are the same as those in Equation II; The definitions of n6, n7, n8, and n9 are the same as those in Equation II; R 10 The definition is the same as the definition of R7 in Equation II, n 10 Indicates substituent R 10 The number of n 10 Choose from 0, 1, 2, 3, 4, or 5, when n 10 When it is greater than 1, each R 10 Same or different, The definition of * is the same as the definition of "*" in Formula II.

[0060] For example, the structure of Formula II is selected from the following groups, whether deuterated or undeuterated:

[0061] , * indicates the site that is confluent with Equation I.

[0062] In some embodiments of this application, Formula I includes segments of ring C, ring D, and X1. Selected from one of the following structures, where "*" represents the connection site between the carbon atom of ring C and ring D, ring B, and the benzene ring, respectively: .

[0063] As a non-restrictive example, fragment Selected from one of the following groups, whether deuterated or undeuterated:

[0064]

[0065] .

[0066] In some embodiments of this application, R1, R2, R3, R4, R5, R6, R7, R8 and R9 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, trimethylsilyl, deuterated trimethylsilyl, substituted or unsubstituted aryl with 6 to 25 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 18 carbon atoms, or substituted or unsubstituted diphenylamino. Among them, the substituents in R1, R2, R3, R4, R5, R6, R7, R8 and R9 are the same or different, and each is independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, trimethylsilyl, deuterated trimethylsilyl, aryl with 6 to 12 carbon atoms or heteroaryl with 3 to 12 carbon atoms.

[0067] In some embodiments of this application, R1, R2, R3, R4, R5, R6, R7, R8, and R9 may be the same or different, and each is independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, deuterated methyl, deuterated trifluoromethyl, trimethylsilyl, deuterated trimethylsilyl, or the group consisting of the following groups or deuterated groups: .

[0068] In some embodiments of this application, ring X, ring Y, or ring Z may be the same or different, and each is independently selected from one or more of the following rings: ; "*" indicates the fusion site of the rings X, Y and Z with the benzene rings substituted by R1, R2 or R3; The substituents in ring X, ring Y and ring Z are selected from the following groups: deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trimethylsilyl, deuterated methyl, deuterated trifluoromethyl, deuterated trimethylsilyl, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, heteroaryl with 3 to 12 carbon atoms, deuterated heteroaryl with 3 to 12 carbon atoms, diphenylamino, deuterated diphenylamino.

[0069] In some embodiments of this application, the compound of formula I is selected from one of formulas I-9 to I-11:

[0070] The definitions of R1~R9 are the same as those in Equation I, R 11 The selectable range is the same as R1~R9, n1~n9, n 11 Each is independently selected from 0 to the maximum number of substitutable numbers.

[0071] In some embodiments of this application, the compound of formula I is selected from one of formulas I-12 to I-14:

[0072] The definitions of R1~R9 are the same as those in Equation I, R 11 The selectable range is the same as R1~R9, n1~n9, n 11 Each is independently selected from 0 to the maximum number of substitutable numbers.

[0073] In some embodiments of this application, the compound of formula I is selected from one of formulas I-15 and I-16:

[0074] The definitions of R1~R9 are the same as those in Equation I, R 11 The selectable range is the same as R1~R9, n1~n9, n 11 Each is independently selected from 0 to the maximum number of substitutable numbers.

[0075] In some embodiments of this application, the compound of formula I is selected from one of formula I-17 and formula I-18:

[0076] The definitions of R1~R9 are the same as those in Equation I, R 11 The selectable range is the same as R1~R9, n1~n9, n 11 Each is independently selected from 0 to the maximum number of substitutable numbers.

[0077] In some embodiments of this application, the organic compound is selected from the group consisting of: .

[0078] Secondly, this application provides an organic electroluminescent device, which includes an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode, the functional layer comprising the organic compound of the first aspect.

[0079] Optionally, the functional layer includes an organic light-emitting layer, which comprises a host material and a guest material, wherein the guest material comprises an organic compound of the first aspect of this application.

[0080] In one specific implementation, the organic electroluminescent device is a green organic electroluminescent device.

[0081] In one specific embodiment, the organic electroluminescent device includes: an anode, a hole transport layer, an organic light-emitting layer, an electron transport layer, and a cathode, which are stacked sequentially.

[0082] Optionally, a hole injection layer may be provided between the anode and the hole transport layer to enhance the ability to inject holes into the hole transport layer.

[0083] Optionally, an electron injection layer may be provided between the cathode and the electron transport layer to enhance the ability to inject electrons into the electron transport layer.

[0084] Optionally, an organic coating layer may also be provided on the cathode.

[0085] In one specific embodiment, the structure of the green organic electroluminescent device is as follows: Figure 1 As shown, the device includes an anode 100, a hole injection layer 310, a first hole transport layer 321, a second hole transport layer 322, an organic light-emitting layer 330, a hole blocking layer 340, an electron transport layer 350, an electron injection layer 360, and a cathode 200, which are stacked sequentially. The hole injection layer 310, the first hole transport layer 321, the second hole transport layer 322, the organic light-emitting layer 330, the hole blocking layer 340, the electron transport layer 350, and the electron injection layer 360 constitute the functional layer 300 of the organic electroluminescent device; the first hole transport layer 321 and the second hole transport layer (light-emitting adjustment layer) 322 constitute the hole transport layer 320.

[0086] Optionally, the anode 100 comprises the following anode materials, preferably those with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials 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 or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto. A transparent electrode comprising indium tin oxide (ITO) is preferred as the anode.

[0087] In some embodiments, the hole transport region 320 includes one or more hole transport materials, which may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, and will not be listed here.

[0088] In one specific embodiment of this application, the first hole transport layer 321 is composed of compound HT-1 ( The second hole transport layer 322 is composed of compound HT-2 ( ) )composition.

[0089] Optionally, a hole injection layer 310 is further provided between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first 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 restrictions on this.

[0090] In one embodiment of this application, the hole injection layer 310 is composed of PD-1 ( ) and compound HT-1 ( )composition.

[0091] Optionally, the organic light-emitting layer 330 may be composed of a single light-emitting material or may include a host material and a guest material.

[0092] Optionally, the organic light-emitting layer 330 is composed of a host material and a guest material. Holes and 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.

[0093] The host material of the organic light-emitting layer 330 may include metal chelating compounds, bis(styrene) derivatives, aromatic amine derivatives, dibenzofuran derivatives, or other types of materials. The host material of the organic light-emitting layer 330 may be one compound or a combination of two or more compounds. This application does not impose any limitations on this.

[0094] In one embodiment of this application, the host material of the organic light-emitting layer 330 includes a first host compound P ( ) and the second main compound N ( ).

[0095] The guest material of the organic light-emitting layer 330 can be selected from compounds with condensed aryl rings or their derivatives, compounds with heteroaryl rings or their derivatives, aromatic amine derivatives, iridium(III) organometallic complexes, platinum(II) organometallic complexes, ruthenium(II) complexes, etc.

[0096] In one embodiment of this application, the guest material of the organic light-emitting layer 330 is an organic compound of this application. The guest material is also referred to as a dopant or dopant.

[0097] In one embodiment of this application, the organic light-emitting layer may further include a sensitizer. The sensitizer may include at least one organometallic compound, a heterocyclic compound, or any combination thereof. The organometallic compound may include ruthenium (Ru), palladium (Pd), rhenium (Re), osmium (Os), platinum (Pt), or any combination thereof. When the organic light-emitting layer includes a sensitizer and a dopant, high exciton energies can be transferred to the sensitizer and then to the dopant. Therefore, deterioration of the dopant is suppressed, and thus lifetime characteristics are improved, and spectral overlap between the sensitizer and the dopant is increased, resulting in efficient (effective) energy transfer. Consequently, the radiative decay rate increases and non-radiative transitions decrease, thereby improving the luminous efficiency of the organic light-emitting device.

[0098] In one embodiment of this application, the sensitizer of the organic light-emitting layer 330 is compound GD1 ( ).

[0099] In one embodiment of this application, the hole-blocking layer 340 includes compound HB-1 ( ).

[0100] In some embodiments of this application, the electron transport layer 350 can be a single-layer structure or a multi-layer structure, and can include one or more electron transport materials. The electron transport materials can typically include metal complexes and / or nitrogen-containing heterocyclic derivatives. The metal complex material can be selected from, for example, LiQ, Alq3, Bepq2, etc.; the nitrogen-containing heterocyclic derivative can be an aromatic ring with a nitrogen-containing six-membered or five-membered ring skeleton, a fused aromatic ring compound with a nitrogen-containing six-membered or five-membered ring skeleton, etc. Specific examples include, but are not limited to, 1,10-phenanthroline compounds such as ET-15, Bphen, NBphen, DBimiBphen, and BimiBphen, or anthracene compounds, triazine compounds, or pyrimidine compounds containing heteroazo aryl groups. The embodiments of this application do not limit the scope of the invention.

[0101] In one embodiment of this application, the electron transport layer 350 is composed of ET-1 ( It consists of ) and LiQ.

[0102] In this application, cathode 200 includes a cathode material that has a small work function and facilitates electron injection into the functional layers. Specific 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; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Optionally, a metal electrode comprising magnesium and silver is included as the cathode.

[0103] Optional, such as Figure 1 As shown, an electron injection layer 360 is further disposed between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic materials. In one embodiment of this application, the electron injection layer 360 includes ytterbium (Yb).

[0104] Thirdly, this application provides an electronic device including the organic electroluminescent device of the second aspect of this application.

[0105] As one implementation method, such as Figure 2 As shown, the provided 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 including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0106] The following examples illustrate the synthesis method of the organic compounds of this application, but this application is not limited thereto.

[0107] Synthesis Examples Those skilled in the art will recognize that the chemical reactions described herein can be suitably used to prepare many of the organic compounds of this application, and other methods for preparing the compounds of this application are considered to be within the scope of this application. For example, the synthesis of those non-illustrative compounds according to this application can be successfully accomplished by those skilled in the art through modification methods, such as appropriately protecting interfering groups, by utilizing other known reagents besides those described herein, or by making some conventional modifications to the reaction conditions. Compounds for which synthetic methods are not mentioned in this application are either commercially available starting materials or starting materials that can be synthesized according to existing techniques.

[0108] 1.1 Synthesis of Intermediate 1-1

[0109] Under nitrogen protection, 1,3-dibromo-5-iodo-2-nitrobenzene (40.7 g, 100 mmol), 4-tert-butylphenylboronic acid (19.6 g, 110 mmol), tetrakis(triphenylphosphine)palladium (2.3 g, 2 mmol), and potassium carbonate (27.6 g, 200 mmol) were added to a 1 L three-necked flask, followed by 500 mL of toluene, 100 mL of ethanol, and 100 mL of deionized water. The reaction mixture was then stirred at 80 °C for 24 h. After the reaction was complete, the mixture was cooled to room temperature and filtered. The collected filtrate was extracted with 400 mL of ethyl acetate and 400 mL of deionized water, and the liquid was separated. The organic phase was washed three times with 500 mL of saturated brine. The organic phase was dried over anhydrous sodium sulfate and concentrated using a rotary evaporator to obtain the crude product. The crude product was purified by silica gel column chromatography using petroleum ether / dichloromethane as the mobile phase to obtain intermediate 1-1 (33.8 g, yield 82%).

[0110] 1.2 Synthesis of intermediates 1-2 to 1-6 Referring to the synthesis of intermediate 1-1, reactants A from Table 1 were used instead of 1,3-dibromo-5-iodo-2-nitrobenzene and B was used instead of 4-tert-butylphenylboronic acid to obtain intermediates 1-2 to 1-6.

[0111] Table 1

[0112] 1.3 Synthesis of intermediates 1-7

[0113] In a three-necked flask equipped with a condenser, m-chloroperoxybenzoic acid (… m- CPBA (81.2 g, 400 mmol, 85% by mass) was dissolved in 1,2-dichloroethane (750 mL), and 2-bromo-6-chloro-4-tert-butylaniline (26.3 g, 100 mmol) was dissolved in 1,2-dichloroethane (250 mL). The solutions were added dropwise to the acid solution. After the system was heated to reflux and reacted for 10 hours, the mixture was cooled to room temperature and the reaction was quenched with a saturated sodium thiosulfate (Na2S2O3) aqueous solution. The solvent was removed under reduced pressure, and the residue was treated with 10% sodium hydroxide (NaOH) solution. The residue was then extracted with ethyl acetate (EtOAc), and the organic phases were combined, washed successively with water and saturated brine, and dried with anhydrous sodium sulfate (Na2SO4). The solvent was removed under reduced pressure, and the crude product was purified by silica gel column chromatography using n-hexane / ethyl acetate as the mobile phase to obtain intermediate 1-7 (26.6 g, 91% yield).

[0114] 2.1 Synthesis of Intermediate 2-1

[0115] Under nitrogen protection, 2,6-dibromonitrobenzene (28.0 g, 100 mmol), 9,9'-spirodifluorene-4-boronic acid (39.6 g, 110 mmol), tetrakis(triphenylphosphine)palladium (2.3 g, 2 mmol), and potassium carbonate (27.6 g, 200 mmol) were added to a 1 L three-necked flask. 500 mL of toluene, 100 mL of ethanol, and 100 mL of deionized water were then added. The reaction mixture was stirred at 80 °C for 24 h. After the reaction was complete, the mixture was cooled to room temperature and filtered. The collected filtrate was extracted with 400 mL of ethyl acetate and 400 mL of deionized water, and the liquid was separated. The organic phase was washed three times with 500 mL of saturated brine, dried over anhydrous sodium sulfate, and concentrated using a rotary evaporator to obtain the crude product. The crude product was purified by silica gel column chromatography using petroleum ether / dichloromethane as the mobile phase to obtain intermediate 2-1 (35.6 g, yield 69%).

[0116] 2.2 Synthesis of intermediates 2-2 to 2-16 Referring to the synthesis method in 2-1, reactant C in Table 2 was used to replace 2,6-dibromonitrobenzene, and reactant D was used to replace 9,9'-spirodifluorene-4-boronic acid to synthesize intermediates 2-2 to 2-16.

[0117] Table 2

[0118] 3.1 Synthesis of Intermediate 3-1

[0119] Under nitrogen protection, intermediate 2-1 (31.0 g, 60 mmol), triphenylphosphine (47.2 g, 180 mmol), and o-dichlorobenzene (200 mL) were added to a three-necked flask and heated to 180 °C, then stirred under reflux for 18 h. After the reaction was completed as detected by TLC, the reaction system was cooled to room temperature, stirring was stopped, the reaction solution was washed with water, the organic phase was separated, and dried over anhydrous MgSO4. The solvent was removed under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using petroleum ether / dichloromethane as the mobile phase to obtain intermediate 3-1 (15.4 g, yield 53%).

[0120] 3.2 Synthesis of intermediates 3-2 to 3-16 Referring to the synthesis method of intermediate 3-1, reactant E from Table 3 was used to replace intermediate 2-1 in the reaction to synthesize intermediates 3-2 to 3-16.

[0121] Table 3

[0122] 4.1 Synthesis of Intermediate 4-1

[0123] Under nitrogen protection, intermediate 3-1 (14.5 g, 30 mmol), 2,6-difluorochlorobenzene (4.9 g, 33 mmol), cesium carbonate (14.7 g, 45 mmol), and anhydrous N,N-dimethylformamide (DMF, 200 mL) were added to a three-necked flask, and the reaction mixture was heated to 120 °C and stirred for 12 h. After the reaction was completed, 300 mL of deionized water was added to quench the reaction and precipitate the product. The product was filtered, and the filter cake was washed three times with deionized water to obtain the crude product. The crude product was purified by silica gel column chromatography using petroleum ether / dichloromethane as the mobile phase to obtain intermediate 4-1 (14.9 g, yield 81%).

[0124] 4.2 Synthesis of intermediates 4-2 to 4-17 Referring to the synthesis method in 4-1, reactant F from Table 4 was used to replace compound 3-1, and reactant G was used to replace compound 2,6-difluorochlorobenzene to synthesize intermediates 4-2 to 4-17.

[0125] Table 4

[0126] 5.1 Synthesis of Intermediate 5-1

[0127] Under nitrogen protection, intermediate 4-1 (15.3 g, 25 mmol) was dissolved in 200 mL of tetrahydrofuran and cooled to -78 °C. A 2.5 M solution of n-butyllithium in n-hexane (11 mL, 27.5 mmol) was added dropwise using a constant-pressure dropping funnel. The reaction mixture was stirred at -78 °C for 2 hours. Then, 9-fluorenone (5.4 g, 30 mmol) was added to the reaction mixture. After the addition was complete, the reaction was continued at -78 °C for 30 minutes, then slowly raised to room temperature and stirred for 12 hours. After the reaction was complete, water was added to quench the reaction, and dichloromethane was added for extraction. The organic phase was collected and dried over anhydrous magnesium sulfate. Next, the organic phase was filtered to obtain a filtrate, and the concentrate was obtained by vacuum distillation. Under nitrogen protection, the concentrate was dissolved in 100 mL of acetic acid solution, and 2 mL of 30% hydrochloric acid solution (24 mmol) was added. The reaction solution was heated to reflux for 12 hours, then cooled to room temperature, and 2 M sodium hydroxide aqueous solution was added dropwise until the pH of the reaction solution was neutral. At this point, 300 mL of dichloromethane was added to extract the above reaction solution three times, the organic phases were combined and dried over MgSO4, filtered, and the filtrate was concentrated under vacuum to obtain a crude product. The crude product was purified by column chromatography using a petroleum ether / dichloromethane mixture as eluent to obtain intermediate 5-1 (11.8 g, yield: 68%).

[0128] 5.2 Synthesis of intermediates 5-2 to 5-13 Referring to the synthesis method in 5-1, reactant H from Table 5 was used to replace intermediate 4-1, and reactant I was used to replace 9-fluorenone to synthesize intermediates 5-2 to 5-13.

[0129] Table 5

[0130] 5.3 Synthesis of intermediate 5-14

[0131] In a flame-dried Schlenk tube, intermediate 4-12 (18.0 g, 25.0 mmol) and 100.0 mL of anhydrous tetrahydrofuran were added under a nitrogen atmosphere. After cooling the system to 0 °C, a solution of magnesium isopropyl chloride in n-hexane (13.5 mL, 2.0 M, 27.0 mmol) was added dropwise to the solution under nitrogen protection. The mixture was stirred at 0 °C for 1.5 h. Then, a solution of fluorenone (5.41 g, 30 mmol) in tetrahydrofuran was slowly added to the reaction mixture under a nitrogen atmosphere. The reaction system was then heated to 80 °C and stirred for 12.0 h before cooling to room temperature. The reaction was quenched with dilute hydrochloric acid, extracted with ethyl acetate, and the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed under reduced pressure. The residue was dissolved in dichloromethane, and a boron trifluoride diethyl ether complex was added. The mixture was stirred at room temperature for 1.0 h, quenched with water, extracted with dichloromethane, and washed with saturated brine. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation. The crude product was purified by silica gel column chromatography using petroleum ether as eluent to obtain intermediate 5-14 (10.4 g, yield: 55%).

[0132] 5.4 Synthesis of intermediates 5-15 to 5-23 Referring to the synthesis method in 5-14, reactant J from Table 6 was used to replace intermediate 4-12, and reactant K was used to replace 9-fluorenone to synthesize intermediates 5-15 to 5-23.

[0133] Table 6

[0134] 6.1 Synthesis of intermediate 6-A-1

[0135] Under nitrogen protection, intermediate 5-1 (14.5 g, 20.9 mmol), carbazole (3.9 g, 23.1 mmol), cesium carbonate (10.3 g, 31.5 mmol), and anhydrous DMF (150 mL) were added to a three-necked flask, and the reaction mixture was heated to 120 °C and stirred for 12 h. After the reaction was completed, 300 mL of deionized water was added to quench the reaction and precipitate the product. The product was filtered, and the filter cake was washed three times with deionized water to obtain the crude product. The crude product was purified by silica gel column chromatography using petroleum ether / dichloromethane as the mobile phase to obtain intermediate 6-A-1 (16.4 g, 93% yield).

[0136] 6.2 Synthesis of intermediate X-1

[0137] Under nitrogen protection, 3,6-dibromocarbazole (32.5 g, 100 mmol), 4-tert-butyl-2,6-dimethylphenylboronic acid (22.7 g, 110 mmol), tetrakis(triphenylphosphine)palladium (2.3 g, 2 mmol), and potassium carbonate (27.6 g, 200 mmol) were added to a 1 L three-necked flask, followed by the addition of 500 mL toluene, 100 mL ethanol, and 100 mL deionized water. The reaction mixture was then stirred at 80 °C for 24 h. After the reaction was complete, the mixture was cooled to room temperature and filtered. The collected filtrate was extracted with 400 mL ethyl acetate and 400 mL deionized water, and the liquid was separated. The organic phase was washed three times with 500 mL saturated brine. The organic phase was dried over anhydrous sodium sulfate and concentrated using a rotary evaporator to obtain the crude product. The crude product was purified by silica gel column chromatography using petroleum ether / dichloromethane as the mobile phase to obtain intermediate X-1 (35.6 g, yield 73%).

[0138] 6.3 Synthesis of intermediates 6-A-2 to 6-A-15 Referring to the synthesis method of 6-A-1, reactants L and M from Table 7 were used to replace intermediates 5-1 and carbazole, respectively, to synthesize intermediates 6-A-2 to 6-A-15.

[0139] Table 7

[0140] 6.4 Synthesis of intermediate 6-B-1

[0141] Under nitrogen protection, intermediate 5-14 (15 g, 19.8 mmol), carbazole (3.15 g, 18.87 mmol), cuprous iodide (360 mg, 1.89 mmol), 1,10-phenanthroline (679.4 mg, 3.77 mmol), potassium phosphate (8.00 g, 37.74 mmol), and DMF (150 mL) were added to a three-necked flask, and the reaction solution was heated to 150 °C and stirred for 24 h. After the reaction was completed, 300 mL of deionized water was added to quench the reaction and precipitate the product. The product was filtered, and the filter cake was washed three times with deionized water to obtain the crude product. The crude product was purified by silica gel column chromatography using petroleum ether / dichloromethane to obtain intermediate 6-B-1 (12.0 g, 72% yield).

[0142] 6.5 Synthesis of intermediates 6-B-2 to 6-B-16 Referring to the synthesis method of 6-B-1, reactants N and O from Table 8 were used to replace intermediates 5-14 and carbazole, respectively, to synthesize compounds 6-B-2 to 6-B-16.

[0143] Table 8

[0144] 7.1 Synthesis of Compound A1

[0145] Under nitrogen protection, intermediate 6-A-1 (12.1 g, 14.3 mmol) and 100 mL of dry tert-butylbenzene were added to a three-necked flask. The system was cooled to -30 °C, and a 1.3 M solution of tert-butyllithium in n-pentane (21.5 mL, 28 mmol) was added dropwise. The reaction mixture was then heated to 60 °C and reacted for 2 hours. The reaction mixture was then cooled back to -30 °C, and boron tribromide (14.3 g, 57 mmol) was added. The reaction mixture was then heated back to 60 °C and stirred for 3 hours. Finally, the reaction mixture was cooled to 0 °C, and a slow dropwise addition of... N,N -Diisopropylethylamine (20 mL, 115 mmol) was added dropwise, and the reaction system was heated to 160 °C and stirred for 24 h. After the reaction was complete, the reaction system was cooled to room temperature, and 100 mL of water and 300 mL of ethyl acetate were added. The mixture was stirred for 30 minutes and then separated. The resulting organic phase was washed three times with 200 mL of water, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was separated by column chromatography using petroleum ether / dichloromethane as the eluent to obtain compound A1 (2.1 g, yield: 18%, mass spectrometry (m / z) = 817.27 [M+H)). + ).

[0146] 7.2 Synthesis of compounds A11 to B246 Referring to the synthesis method of compound A1, reactant P from Table 9 was used to replace compound 6-A-1 in the reaction to synthesize compounds A2 to B246. The mass spectra (m / z) are the mass spectrometry data of the synthesized compounds.

[0147] Table 9

[0148] 8.1 Synthesis of Compound A59

[0149] 1) Under a nitrogen atmosphere, compound 6-A-2 (20.5 g, 20.3 mmol) and 100 mL of deuterium benzene were added to a three-necked flask. The mixture was heated to 60 °C, and then trifluoromethanesulfonic acid (15 g, 100 mmol) was slowly added. The mixture was then heated to boiling and stirred for 24 hours. After the reaction system cooled to room temperature, 100 mL of heavy water was added, and the mixture was stirred for 10 minutes. The mixture was then separated while hot. The organic phase was washed three times with 100 mL of heavy water, and the organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the filtrate was distilled under reduced pressure to remove the solvent, yielding a crude product. The crude product was separated by column chromatography using petroleum ether / dichloromethane as the eluent to obtain compound 6-A-2a (11.5 g, yield: 53%).

[0150] 2) Under nitrogen protection, intermediate 6-A-2a (10.7 g, 10 mmol) and 100 mL of dry tert-butylbenzene were added to a three-necked flask. The system was cooled to -30 °C, and a 1.3 M tert-butyllithium solution in n-pentane (15.5 mL, 20.1 mmol) was added dropwise. The reaction system was then heated to 60 °C and reacted for 2 hours. The reaction solution was then cooled back to -30 °C, boron tribromide (10.2 g, 40 mmol) was added, and the reaction solution was heated back to 60 °C and stirred for 3 hours. The reaction system was then cooled to 0 °C, and a slow dropwise addition of... N,N -Diisopropylethylamine (14 mL, 80 mmol) was added dropwise, and the reaction system was heated to 160 °C and stirred for 24 h. After the reaction was complete, the reaction system was cooled to room temperature, and 100 mL of water and 100 mL of ethyl acetate were added. The mixture was stirred for 30 minutes and then separated. The resulting organic phase was washed three times with 100 mL of water, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was separated by column chromatography using petroleum ether / dichloromethane as the eluent to obtain compound A59 (1.4 g, yield: 13%, mass spectrometry (m / z) = 1042.82 [M+H)). + ).

[0151] 8.2 Synthesis of Compound B63 Following the synthetic route of compound A59, intermediate 6-B-3 was used instead of compound 6-A-2 to yield compound B63. The combined yield of the two steps was 7.1%, and the mass spectrometry result (m / z) was 1331.16 [M+H].+ .

[0152]

[0153] NMR data for some compounds: Table 10

[0154] Fabrication and evaluation of organic electroluminescent devices: Example 1: Green Organic Electroluminescent Device The anode pretreatment is performed through the following process: On an ITO substrate with a thickness of 1000 Å, the surface is treated with ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. The surface of the ITO substrate is cleaned with organic solvent (ethanol / isopropanol) to remove impurities and oil stains.

[0155] On the experimental substrate (anode), PD-1:HT-1 were co-deposited at a deposition rate ratio of 2%:98% to form a hole injection layer with a thickness of 100 Å.

[0156] Compound HT-1 was vacuum-deposited onto the hole injection layer to form a first hole transport layer with a thickness of 1040 Å.

[0157] Compound HT-2 was vacuum-deposited onto the first hole transport layer to form a second hole transport layer with a thickness of 455 Å.

[0158] On the second hole transport layer, compound P was used as the first host, compound N as the second host, and compounds A1 and GD1 as dopants. An organic light-emitting layer was prepared by co-evaporation. Specifically, the materials of compound P: compound N: compound GD1: compound A1 were co-deposited at a deposition rate ratio of 55.3%: 36.9%: 7%: 0.8% to form an organic light-emitting layer with a thickness of 360 Å.

[0159] On the organic light-emitting layer, compound HB-1 is vacuum-deposited to form a hole-blocking layer with a thickness of 50 Å.

[0160] On the hole blocking layer, compounds ET-1 and LiQ were co-deposited at a 1:1 evaporation rate ratio to form an electron transport layer with a thickness of 295 Å.

[0161] Yb was deposited on the electron transport layer to form an electron injection layer with a thickness of 15 Å. Then, magnesium (Mg) and silver (Ag) were co-deposited at a deposition rate ratio of 1:9 and vacuum-deposited on the electron injection layer to form a cathode with a thickness of 1000 Å.

[0162] Furthermore, compound CP-1 is vacuum-deposited onto the aforementioned cathode to form an organic coating layer with a thickness of 480 Å, thereby completing the fabrication of the green organic electroluminescent device.

[0163] Examples 2-33 Except that, when preparing the organic light-emitting layer, the organic electroluminescent device was prepared using the same method as in Example 1, except that the compounds in Table 11 below were used instead of compound A1 in Example 1.

[0164] Comparative Examples 1-3 Except that when forming the organic light-emitting layer, compound A1 was replaced with compounds A, B, and C in Table 11 below, the organic electroluminescent device was prepared using the same method as in Example 1.

[0165] The main materials used in the above embodiments and comparative examples are shown below.

[0166]

[0167] The performance of the green photosensitized devices prepared in Examples 1-33 and Comparative Examples 1-3 was tested. Specifically, the voltage, efficiency and lifetime characteristics of the devices were tested under J15. The test results are shown in Table 11.

[0168] Table 11

[0169] Referring to Table 11 above, it can be seen that in Examples 1-33, the compounds of the present invention were used as doping materials, and compared with Comparative Examples 1-3, the luminous efficiency was improved by at least 17.0%, and the device lifetime was improved by at least 10.2%. It is evident that using the organic compounds of this application in the organic light-emitting layer of organic electroluminescent devices can effectively improve the luminous efficiency and T95 lifetime of organic electroluminescent devices. The reason for this is that introducing dual spirofluorenes on the same side of the BN resonance structure—that is, replacing carbazole with spirofluorene-carbazole on the basis of a single spirofluorene boron nitrogen material—allows two spirofluorenes to connect or fuse with the same carbazole. This can enhance the rigidity of the molecular skeleton while forming a larger molecular conjugated plane, effectively reducing the influence of the large conjugated plane on molecular stability, improving the thermal and chemical stability of the molecules, and thus improving the lifetime of OLED devices. Simultaneously, this configuration can control the size of the molecular conjugated plane and increase the intermolecular distance of the luminescent material, suppressing strong π-π interactions between molecules, effectively preventing intermolecular stacking, and improving molecular luminous efficiency. In summary, the compounds in this application can simultaneously improve the core indicators of OLED devices, such as efficiency and lifespan.

[0170] The preferred embodiments of this application have been described in detail above. However, this application is not limited to the specific details of the above embodiments. Within the scope of the technical concept of this application, various simple modifications can be made to the technical solution of this application, and these simple modifications all fall within the protection scope of this application.

[0171] It should also be noted that the various specific technical features described in the above embodiments can be combined in any suitable manner without contradiction. In order to avoid unnecessary repetition, this application will not describe the various possible combinations separately.

Claims

1. An organic compound, characterized in that, The organic compound has the structure shown in Formula I: In this case, one of ring A and ring B is selected from the structure shown in Formula II, and the other is selected from a substituted or unsubstituted aromatic ring with 6 to 40 carbon atoms or a substituted or unsubstituted heteroaromatic ring with 12 to 40 carbon atoms. "*" indicates the fusion site between the structure shown in Formula II and the structure shown in Formula I. Any three adjacent fusion sites in Formula II are fused with Formula I. The substituents in ring A and ring B may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, deuterated trialkylsilyl with 3 to 12 carbon atoms, aryl with 6 to 30 carbon atoms, deuterated aryl with 6 to 30 carbon atoms, heteroaryl with 3 to 30 carbon atoms, deuterated heteroaryl with 3 to 30 carbon atoms, arylamine with 12 to 20 carbon atoms, or deuterated arylamine with 12 to 20 carbon atoms; X1 and X2 may be the same or different, and each is independently selected from single bonds, O, S, C(R) bonds. a R b ) or N(R c ); R a R b and R c They may be the same or different, and each independently selected from alkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 18 carbon atoms, deuterated aryl groups having 6 to 18 carbon atoms, haloaryl groups having 6 to 18 carbon atoms, aryl groups substituted with alkyl or deuterated alkyl groups having 1 to 5 carbon atoms, or deuterated aryl groups substituted with alkyl or deuterated alkyl groups having 1 to 5 carbon atoms; Optional, R a and R b The carbon atoms that are connected to each other form a ring W, wherein the ring W is selected from cycloalkanes with 3 to 8 carbon atoms or aromatic rings with 6 to 13 carbon atoms; Rings C, D, E, and F may be the same or different, and each is independently selected from aromatic rings with 6 to 30 carbon atoms or heteroaromatic rings with 3 to 30 carbon atoms; R1, R2, R3, R4, R5, R6, R7, R8, and R9 may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, deuterated trialkylsilyl with 3 to 12 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms, or substituted or unsubstituted aromatic amino with 12 to 20 carbon atoms; The substituents in R1, R2, R3, R4, R5, R6, R7, R8, and R9 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or deuterated heteroaryl with 3 to 20 carbon atoms; n1 represents the number of substituents R1, which is selected from 0, 1, 2 or 3. When n1 is greater than 1, each R1 may be the same or different. Optionally, any two adjacent R1s are connected to form a substituted or unsubstituted 6- to 15-membered ring X. n2 represents the number of substituents R2, which is selected from 0, 1, 2, 3 or 4. When n2 is greater than 1, each R2 may be the same or different. Optionally, any two adjacent R2s are connected to form a substituted or unsubstituted 6- to 15-membered ring Y. n3 represents the number of substituents R3, which is selected from 0, 1 or 2. When n3 is 2, each R3 may be the same or different. Optionally, any two adjacent R3s are connected to form a substituted or unsubstituted 6- to 15-membered ring Z. n4 represents the number of substituents R4, which is selected from 0 to the maximum number of substitutable elements. When n4 is greater than 1, each R4 may be the same or different. n5 represents the number of substituents R5, which is selected from 0 to the maximum number of substitutable elements. When n5 is greater than 1, each R5 may be the same or different. n6 represents the number of substituents R6, and n6 is selected from 0 or 1; n7 represents the number of substituents R7, which can be selected from 0, 1, 2, 3 or 4. When n7 is greater than 1, the R7s may be the same or different. n8 represents the number of substituents R8, which is selected from 0 to the maximum number of substitutable elements. When n8 is greater than 1, each R8 may be the same or different. n9 represents the number of substituents R9, which is selected from 0 to the maximum number of substitutable elements. When n9 is greater than 1, each R9 may be the same or different. The substituents in ring X, ring Y, and ring Z may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, trimethylsilyl, deuterated trimethylsilyl, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, heteroaryl with 3 to 12 carbon atoms, deuterated heteroaryl with 3 to 12 carbon atoms, aromatic amino with 12 to 20 carbon atoms, or deuterated aromatic amino with 12 to 20 carbon atoms.

2. The organic compound according to claim 1, characterized in that, One of ring A and ring B is selected from the structure shown in Formula II, and the other is selected from a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthyl ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted tetrahydronaphthyl ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted spirofluorene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted biphenyl ring, a substituted or unsubstituted phenyldibenzothiophene ring, a substituted or unsubstituted phenyldibenzofuran ring, or a substituted or unsubstituted phenylcarbazole ring. The substituents in ring A or ring B are one or more. When there are multiple substituents in ring A or ring B, each substituent may be the same or different, and each is independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, trimethylsilyl, deuterated trimethylsilyl, aryl with 6 to 18 carbon atoms, deuterated aryl with 6 to 18 carbon atoms, heteroaryl with 3 to 18 carbon atoms, deuterated heteroaryl with 3 to 18 carbon atoms, substituted or unsubstituted diphenylamino, or substituted or unsubstituted deuterated diphenylamino.

3. The organic compound according to claim 1 or 2, characterized in that, One of ring A or ring B is selected from the structure shown in Formula II, and the other is selected from the group consisting of deuterated or undeuterated groups: ； "*" indicates the connection point between ring A or ring B and formula I.

4. The organic compound according to claim 1, characterized in that, Rings C, D, E, and F may be the same or different, and each is independently selected from benzene rings, naphthalene rings, phenanthrene rings, anthracene rings, benzofuran rings, dibenzofuran rings, benzothiophene rings, and dibenzothiophene rings. N -Phenylindole ring, N -Phenylacetylcarbazole ring, indene ring, fluorene ring, pyridine ring, pyrimidine ring, benzopyridine ring, benzopyrimidine ring, naphthopyridine ring, or naphthopyrimidine ring.

5. The organic compound according to claim 1, characterized in that, Formula II is selected from one of the following structures: ； The definitions of R6, R7, R8 and R9 are the same as those in claim 1; The definitions of n6, n7, n8, and n9 are the same as those in claim 1; R 10 The definition is the same as that of R7 in claim 1, n 10 Indicates substituent R 10 The number of n 10 Choose from 0, 1, 2, 3, 4, or 5, when n 10 When it is greater than 1, each R 10 Same or different.

6. The organic compound according to claim 1, characterized in that, Equation I contains segments of rings C, D, and X1. Selected from one of the following structures, where "*" represents the connection site between the carbon atom of ring C and ring D, ring B, and the benzene ring, respectively: 。 7. The organic compound according to claim 1, characterized in that, R1, R2, R3, R4, R5, R6, R7, R8, and R9 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, trimethylsilyl, deuterated trimethylsilyl, substituted or unsubstituted aryl with 6 to 25 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 18 carbon atoms, or substituted or unsubstituted diphenylamino. Among them, the substituents in R1, R2, R3, R4, R5, R6, R7, R8 and R9 are the same or different, and each is independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, trimethylsilyl, deuterated trimethylsilyl, aryl with 6 to 12 carbon atoms or heteroaryl with 3 to 12 carbon atoms.

8. The organic compound according to claim 1 or 7, characterized in that, R1, R2, R3, R4, R5, R6, R7, R8, and R9 may be the same or different, and each is independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, deuterated methyl, deuterated trifluoromethyl, trimethylsilyl, deuterated trimethylsilyl, deuterated or undeuterated groups: 。 9. The organic compound according to claim 1, characterized in that, Rings X, Y, and Z may be the same or different, and each is independently selected from one or more of the following rings: ； "*" indicates the fusion site of ring X, ring Y and ring Z with the benzene ring substituted by R1, R2 or R3; The substituents in ring X, ring Y and ring Z are each independently selected from the following groups: deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trimethylsilyl, deuterated methyl, deuterated trifluoromethyl, deuterated trimethylsilyl, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, heteroaryl with 3 to 12 carbon atoms, deuterated heteroaryl with 3 to 12 carbon atoms, diphenylamino or deuterated diphenylamino.

10. The organic compound according to claim 1, characterized in that, The organic compound is selected from the group consisting of the following compounds: 。 11. An organic electroluminescent device, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode, characterized in that, The functional layer comprises any one of the organic compounds according to claims 1 to 10.

12. The organic electroluminescent device according to claim 11, characterized in that, The functional layer includes an organic light-emitting layer, which comprises a host material and a guest material, wherein the guest material contains the organic compound.

13. An electronic device, characterized in that, The electronic device includes the organic electroluminescent device as described in claim 11 or 12.

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