Organic compound, organic electroluminescent device, and electronic apparatus

Abstract

The present application relates to an organic compound, an organic electroluminescent device, and an electronic apparatus. The organic compound provided in the present application has a structure as represented by formula I. Applying the organic compound to organic electroluminescent devices can significantly improve the performance of the devices.

Description

Organic compounds, organic electroluminescent devices and electronic devices

[0001] Cross-references to related applications

[0002] This application claims priority to Chinese patent application No. 202411640343.4, filed on November 15, 2024, the entire contents of which are incorporated herein by reference. Technical Field

[0003] This application relates to the field of organic electroluminescence, specifically to an organic compound, an organic electroluminescent device, and an electronic device. Background Technology

[0004] Organic electroluminescence (OEC) is one of the most researched and fastest-developing display technologies in recent years, widely recognized as one of the most promising flat panel display technologies that could potentially replace liquid crystal displays. OEC in organic materials is an injection-type recombination emission mechanism. Its emission mechanism involves holes and electrons generated at the positive and negative electrodes recombinating into excitons within the light-emitting material. The excitons' energy is transferred to the light-emitting molecules, exciting electrons in the molecules to an excited state. This excited state is unstable, and the process of returning from the excited state to the ground state produces visible light. To enhance the injection and transport capabilities of electrons and holes, several functional layers composed of organic materials are typically added between the substrate and the organic light-emitting layer. Among these, a light-emitting adjustment layer is needed to regulate the balance between hole injection and transport.

[0005] Currently, the most commonly used luminescence modulating layer materials are triarylamine compounds. To ensure high hole mobility, these molecules typically contain planar structures. However, this leads to poor structural stability and weak electron tolerance, resulting in luminescence modulating layers made from these materials exhibiting poor electron and exciton blocking effects, leading to low device efficiency and lifetime. Therefore, it is necessary to optimize the molecular structure to enhance electron blocking and better regulate hole injection and transport, thereby obtaining devices with superior performance.

[0006] Meanwhile, in addition to common issues such as device lifespan and efficiency, color shift and crosstalk at low brightness are increasingly attracting industry attention. With advancements in organic light-emitting diode (OLED) display technology, consumers have increasingly higher demands for visual experience. In recent years, terminal electronic display manufacturers have raised extremely high requirements for color display at low brightness, but current device and material systems cannot simultaneously meet the demands of low voltage, high efficiency, and long lifespan. Therefore, it is necessary to develop new material systems to further improve the overall performance of OLED devices. Summary of the Invention

[0007] The purpose of this application is to provide an organic compound, an organic electroluminescent device, and an electronic device, wherein using the organic compound in the organic electroluminescent device can improve the performance of the device.

[0008] A first aspect of this application provides an organic compound having the structure shown in Formula I:

[0009] Where X and Y are the same or different, and each is independently selected from single bonds, C(R) ... a R b ), N(R c ), O, S, C(R) d () or N; and X and Y are not both single bonds;

[0010] R a R b R c and R d They may be the same or different, and each is independently selected from substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 40 carbon atoms;

[0011] Optional, R a and R b Forming 3- to 15-member saturated or unsaturated rings;

[0012] R a R b R c and R d The substituents in the group 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, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, deuterated heteroaryl with 3 to 20 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, or triarylsilyl with 18 to 24 carbon atoms;

[0013] L1 and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 12 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms;

[0014] The substituents in L1 and L2 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, aryl with 6 to 10 carbon atoms, and heteroaryl with 3 to 12 carbon atoms.

[0015] One of R1 and R2 is selected from hydrogen or deuterium, and the other is selected from substituted or unsubstituted aryl groups with 6 to 12 carbon atoms;

[0016] R3 and R4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 10 carbon atoms;

[0017] The substituents in R1, R2, R3 and R4 may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, and haloalkyl with 1 to 5 carbon atoms.

[0018] Each of R5, R6, R7, R8 and R9 may be the same or different, and each is independently selected from hydrogen, deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, and haloalkyl with 1 to 10 carbon atoms.

[0019] a is the number of R5s, and a is selected from 1 or 2. When a is greater than 1, any two R5s are the same or different.

[0020] b is the number of R6s, and b is selected from 1, 2, 3, 4 or 5. When b is greater than 1, any two R6s are the same or different.

[0021] c is the number of R7s, and c is selected from 1, 2 or 3. When c is greater than 1, any two R7s are the same or different.

[0022] d is the number of R8s, which can be selected from 1, 2 or 3. When d is greater than 1, any two R8s are the same or different. Optionally, any two adjacent R8s form a 3 to 15-element saturated or unsaturated ring.

[0023] e is the number of R9s, which can be selected from 1, 2, 3 or 4. When e is greater than 1, any two R9s can be the same or different. Optionally, any two adjacent R9s can form a 3 to 15-element saturated or unsaturated ring.

[0024] A second aspect of 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 comprises the aforementioned organic compound.

[0025] A third aspect of this application provides an electronic device including the organic electroluminescent device described in the second aspect.

[0026] The organic compound described in this application is composed of a 3,4-disubstituted phenyl group. 2,3- or 2,5-disubstituted phenyl groups and diaryl pentane / hexa-membered ring groups The resulting aromatic amine compound contains two sets of disubstituted phenyl groups, both of which are small-volume aryl groups, such as phenyl, naphthyl, or biphenyl groups with fully conjugated regions. The compound employs two sets of small-volume aryl polyortho-substituents with different configurations to form a highly twisted structure. Due to its high spatial twist configuration, the material exhibits better film-forming properties. Using it as a light-emitting adjustment layer in OLED devices can effectively suppress lateral carrier migration, thereby improving leakage current and significantly improving color shift at low brightness. Simultaneously, the 3,4-disubstituted phenyl groups are selected from phenyl or naphthyl groups, which can adjust the HOMO energy level to be deeper and the LUMO energy level to be shallower, thus increasing the band gap (Eg). Furthermore, combined with the planar structure of the diaryl pentane five / six-membered ring groups in the molecule, the introduction of the polysubstituted structure can improve the planar rigidity of the molecule, thereby reducing the evaporation temperature and the risk of decomposition during long-term evaporation, thus improving the yield and lifespan of the device. Specifically, when the compound of this application is applied to the double-layer light-emitting adjustment layer of an OLED device, especially the first light-emitting adjustment layer near the hole transport layer, it can effectively block electrons and recombination excitons, which can significantly improve the efficiency of the device and greatly improve its lifetime.

[0027] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description

[0028] 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.

[0029] Figure 1 is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.

[0030] Figure 2 is a schematic diagram of an electronic device according to one embodiment of this application.

[0031] Reference numerals 100, 200, 300, 310, 320, 321, 322, 330, 331, 340, 350, 400, and 400, respectively, are also listed. Detailed Implementation

[0032] 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.

[0033] In a first aspect, this application provides an organic compound having the structure shown in Formula I:

[0034] Where X and Y are the same or different, and each is independently selected from single bonds, C(R) ... a R b ), N(R c ), O, S, C(R) d () or N; and X and Y are not both single bonds;

[0035] R a R b R c and R d They may be the same or different, and each is independently selected from substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 40 carbon atoms;

[0036] Optional, R a and R b Forming 3- to 15-member saturated or unsaturated rings;

[0037] R a R b R c and R d The substituents in the group 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, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, deuterated heteroaryl with 3 to 20 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, or triarylsilyl with 18 to 24 carbon atoms;

[0038] L1 and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 12 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms;

[0039] The substituents in L1 and L2 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, aryl with 6 to 10 carbon atoms, and heteroaryl with 3 to 12 carbon atoms.

[0040] One of R1 and R2 is selected from hydrogen or deuterium, and the other is selected from substituted or unsubstituted aryl groups with 6 to 12 carbon atoms;

[0041] R3 and R4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 10 carbon atoms;

[0042] The substituents in R1, R2, R3 and R4 may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, and haloalkyl with 1 to 5 carbon atoms.

[0043] Each of R5, R6, R7, R8 and R9 may be the same or different, and each is independently selected from hydrogen, deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, and haloalkyl with 1 to 10 carbon atoms.

[0044] a is the number of R5s, and a is selected from 1 or 2. When a is greater than 1, any two R5s are the same or different.

[0045] b is the number of R6s, and b is selected from 1, 2, 3, 4 or 5. When b is greater than 1, any two R6s are the same or different.

[0046] c is the number of R7s, and c is selected from 1, 2 or 3. When c is greater than 1, any two R7s are the same or different.

[0047] d is the number of R8s, which can be selected from 1, 2 or 3. When d is greater than 1, any two R8s are the same or different. Optionally, any two adjacent R8s form a 3 to 15-element saturated or unsaturated ring.

[0048] e is the number of R9s, which can be selected from 1, 2, 3 or 4. When e is greater than 1, any two R9s can be the same or different. Optionally, any two adjacent R9s can form a 3 to 15-element saturated or unsaturated ring.

[0049] In this application, the descriptive phrases "each...independently is" and "...independently is" and "...independently selected from" are interchangeable and should be interpreted broadly. They can mean either that the specific options expressed by the same symbol in different groups do not affect each other, or that the specific options expressed by the same symbol in the same group do not affect each other. For example, " In this formula, each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine or chlorine. The meaning is as follows: Formula Q-1 indicates that there are q substituents R" on the benzene ring. Each R" can be the same or different, and the options of each R" do not affect each other. Formula Q-2 indicates that there are q substituents R" on each benzene ring of biphenyl. The number q of substituents R" on the two benzene rings can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.

[0050] In this application, the terms "optional" or "optionally" mean that the event or situation described below may, but does not necessarily, occur; this description includes the possibility that the event or situation may or may not occur. For example, "optionally, any two adjacent substituents form a ring" means that any two adjacent substituents may form a ring but are not required to do so, including both scenarios where two adjacent substituents form a ring and scenarios where two adjacent substituents do not form a ring. Similarly, "optionally, R..." a and R b "Forming 3- to 15-member saturated or unsaturated rings" includes: R a and R b The scenario of forming a loop and R a and R b Situations where a loop is not formed.

[0051] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have substituents (hereinafter, for ease of description, substituents are collectively referred to as Rp). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rp or an unsubstituted aryl group. The aforementioned substituent, i.e., Rp, can be, for example, deuterium, halogen, cyano, alkyl, deuterated alkyl, haloalkyl, cycloalkyl, aryl, heteroaryl, deuterated aryl, deuterated heteroaryl, trialkylsilyl, triarylsilyl, etc. The number of substituents can be one or more.

[0052] In this application, the phrase "forming a 3- to 15-membered saturated or unsaturated ring" refers to a saturated or unsaturated ring, where a saturated ring is, for example, cyclopropane. Cyclopentane Cyclohexane adamantane Unsaturated rings, such as benzene rings Naphthalene ring fluoran oxane ring or thione ring For example, optionally, R a and R b Formation of cyclopentane Cyclohexane adamantane benzene ring fluoran oxane ring or thione ring For example, optionally, any two adjacent R8s form a benzene ring. For example, optionally, any two adjacent R9s form a benzene ring.

[0053] In this application, a non-positioned linker bond refers to a single bond extending from the ring system. This means that one end of the linking bond can connect to any position in the ring system that the bond passes through, and the other end connects to the rest of the compound molecule.

[0054] In this application, "*" indicates a site where the aromatic ring is fused with an adjacent ring.

[0055] For example, as shown in equation (f) below, the naphthyl group represented by equation (f) is connected to other positions in the molecule through two non-positional linkages that span the bicyclic ring. This means that any possible connection mode is shown in equations (f-1) to (f-10).

[0056] For example, as shown in the following formula (X'), the dibenzofuran group represented by formula (X') is connected to other positions of the molecule through a non-positional linker extending from the middle of one side of the benzene ring. This means that any possible connection mode shown in formulas (X'-1) to (X'-4) is included.

[0057] 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).

[0058] In this application, R a R b R c R d The number of carbon atoms in L1, L2, R1, R2, R3, and R4 refers to the total number of carbon atoms. For example, if R... c If the aryl group is selected from a substituted aryl group with 12 carbon atoms, then the total number of carbon atoms in the aryl group and its substituents is 12.

[0059] In this application, "alkyl" can include straight-chain alkyl or branched alkyl. "Alkyl with 1 to 10 carbon atoms" can have 1 to 10 carbon atoms. In this application, numerical ranges such as "1 to 10" refer to integers within a given range; for example, "1 to 10 carbon atoms" means an alkyl group that may contain 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms. Specific examples include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, etc.

[0060] In this application, cycloalkyl refers to a group derived from a saturated cyclic carbon chain structure. "Cycloalkyl with 3 to 10 carbon atoms" can have 3 to 10 carbon atoms. In this application, numerical ranges such as "3 to 10" refer to integers within a given range; for example, "5 to 10 carbon atoms" means that it can contain 5, 6, 7, 8, 9, or 10 carbon atoms. Optionally, specific embodiments of cycloalkyl include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, norbornyl, etc.

[0061] In this application, aryl refers to any optional functional group or substituent derived from an aromatic carbon ring. The aryl group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, the 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 the aryl group in this application. Fused-ring aryl groups may include, for example, bicyclic fused aryl (e.g., naphthyl), tricyclic fused aryl (e.g., phenanthrene, fluorene, anthracene), etc. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, spirodifluorenyl, adamantanespirofluorenyl, cyclopentanespirofluorenyl, cyclohexanespirofluorenyl, anthraceneyl, phenanthryl, biphenyl, terphenyl, perylene, pyrene, benzo[fluor]anthrayl, etc. 9,10-dihydroanthracene (e.g., 9,10-dihydroanthracene) For example, 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 this application, biphenyl can be understood as a phenyl-substituted aryl group or an unsubstituted aryl group.

[0062] In this application, the term "hybrid aryl" refers to a divalent or polyvalent group formed by the further loss of one or more hydrogen atoms from a heteroaryl group.

[0063] In this application, a substituted aryl group refers to an aryl group in which one or more hydrogen atoms are replaced by other groups. For example, at least one hydrogen atom may be replaced by a deuterium, halogen group, cyano, alkyl, deuterated alkyl, haloalkyl, cycloalkyl, aryl, heteroaryl, deuterated aryl, deuterated heteroaryl, trialkylsilyl, or triarylsilyl group. It is understood that the number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and its substituents. For example: R a for Therefore, it has 10 carbon atoms.

[0064] In this application, aryl groups used as substituents include, but are not limited to, phenyl, naphthyl, and biphenyl groups.

[0065] 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.

[0066] In this application, terphenyl includes

[0067] 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 at least one 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 thiophene, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinel, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolinyl, indolyl, carbazole, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazole (e.g.) ), benzothiophene, dibenzothiophene, thienzothiophene, benzofuran, phenanthroline, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silanyl, dibenzofuranyl, and N-arylcarbazoyl (such as N-phenylcarbazoyl), N-heteroarylcarbazoyl (such as N-pyridylcarbazoyl), N-alkylcarbazoyl (such as N-methylcarbazoyl), oxanthyl Xanthracene spirofluorene Thioxanespirofluorene And so on, but not limited to these. Among them, thiopheneyl, furanyl, phenanthroline, etc., are heteroaryl groups of the single aromatic ring type, while N-arylcarbazolyl (such as N-phenylcarbazolyl) and N-heteroarylcarbazolyl are heteroaryl groups of the polycyclic system type linked by carbon-carbon conjugation. For example, in this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl groups can be 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, etc.

[0068] In this application, the term "hybrid aryl" refers to a divalent or polyvalent group formed by the further loss of one or more hydrogen atoms from a heteroaryl group.

[0069] 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 group, cyano, alkyl, deuterated alkyl, haloalkyl, cycloalkyl, aryl, heteroaryl, deuterated aryl, deuterated heteroaryl, trialkylsilyl, triarylsilyl, etc.

[0070] It should be understood that the number of carbon atoms in a substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on it.

[0071] In this application, the heteroaryl group used as a substituent includes, but is not limited to, dibenzofuranyl, dibenzothiophenyl, carbazoyl, etc.

[0072] In this application, the hydrogen atoms in the compound structure include various isotopes of hydrogen, such as hydrogen (H), deuterium (D), or tritium (T).

[0073] In this application, "deuterated" means that at least one hydrogen ("H") in a compound or group is replaced by deuterium ("D"); specifically, a deuterated compound or deuterated group can be one, more or all of the available hydrogens that have been replaced by deuterium.

[0074] In this application, the halogen group can be fluorine, chlorine, bromine, or iodine.

[0075] In this application, a haloalkyl group can be an alkyl group in which one or more hydrogen atoms are replaced by halogen atoms. Specific examples of haloalkyl groups include, but are not limited to, trifluoromethyl.

[0076] In this application, a deuterated alkyl group can be an alkyl group in which one or more hydrogen atoms are replaced by deuterium. Specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0077] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl groups.

[0078] In this application, specific examples of triarylsilyl groups include, but are not limited to, triphenylsilyl groups.

[0079] In this application, It refers to the chemical bond that connects with other groups.

[0080] In this application, the deuterated aryl group can be one or more hydrogen atoms (H) of the aryl group that are replaced by deuterium (D). Specific examples of deuterated aryl groups include, but are not limited to, pentadeuterated phenyl and heptadeuterated naphthyl.

[0081] In this application, a deuterated heteroaryl group can be a heteroaryl group in which one or more hydrogen atoms are replaced by deuterium. Specific examples of deuterated heteroaryl groups include, but are not limited to, heptadeuterated dibenzofuranyl.

[0082] In this application, in formula 1 Representation, structure It can be linked to the structure via L1 (L1 single bond, arylene, or heteroarylene). Any substituted site in can be connected to At any position shown in 1, 2, 3, 4, 5, 6, 7, 8, 9, 10. Specifically, when X or Y is selected from N, It can be attached to the N atom via L1: For example, when X or Y is selected from C(R) d )hour, It can be connected to C(R) via L1 d On the C atom of ) Among them, X, Y, L1, R d The definitions of each R8 and each R9 are the same as in Equation I.

[0083] In some embodiments, each of R5, R6, R7, R8 and R9 may be the same or different, and each is independently selected from hydrogen, deuterium, halogen group, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, and deuteralkyl with 1 to 5 carbon atoms.

[0084] Optionally, any two adjacent R8s can form a 5- to 10-element saturated or unsaturated ring;

[0085] Optionally, any two adjacent R9s can form a 5- to 10-element saturated or unsaturated ring.

[0086] In some embodiments, each of R5, R6, R7, R8 and R9 may be the same or different, and each is independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, trifluoromethyl, and trideuterated methyl.

[0087] Optionally, any two adjacent R8 atoms form a benzene ring.

[0088] Optionally, any two adjacent R9s form a benzene ring.

[0089] In some implementations, R a R b R c and R d They may be the same or different, and each is independently selected from substituted or unsubstituted alkyl groups having 1 to 5 carbon atoms, and substituted or unsubstituted aryl groups having 6 to 18 carbon atoms; optionally, R a and R b It forms 5 to 14 saturated or unsaturated rings.

[0090] Furthermore, when R a R b R c and R d When the alkyl groups are the same or different, and each is independently selected from substituted or unsubstituted alkyl groups having 1 to 5 carbon atoms, the alkyl group has 1, 2, 3, 4, or 5 carbon atoms; when R a R b R c and R d When the aryl groups are the same or different and are each independently selected from substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, the number of carbon atoms of the aryl group is selected from 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18.

[0091] Optionally, R a R b R c and R d The substituents in the group may be the same or different, and each is independently selected from deuterium, halogen group, cyano group, alkyl group with 1 to 5 carbon atoms, haloalkyl group with 1 to 5 carbon atoms, deuteralkyl group with 1 to 5 carbon atoms, or trimethylsilyl group.

[0092] In some implementations, R a R b R c and R d The same or different, and each independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, phenyl, naphthyl, biphenyl, terphenyl, pentadeuterated phenyl, or heptadeuterated naphthyl; optionally, R a and R b Formation of cyclopentane Cyclohexane adamantane fluoran oxane ring or thione ring

[0093] In some implementations, in formula I, Selected from the group consisting of the following groups:

[0094] In some implementations, in formula I, Selected from the group consisting of the following groups:

[0095] In some embodiments, L1 and L2 may be the same or different, and each is independently selected from single bonds or substituted or unsubstituted aryl groups having 6 to 12 carbon atoms.

[0096] Furthermore, when L1 and L2 are the same or different, and each is independently selected from substituted or unsubstituted arylene groups having 6 to 12 carbon atoms, the number of carbon atoms in the arylene group is selected from 6, 7, 8, 9, 10, 11 or 12.

[0097] Optionally, the substituents in L1 and L2 may be the same or different, and each may be independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 5 carbon atoms, deuterated alkyl groups with 1 to 5 carbon atoms, haloalkyl groups with 1 to 5 carbon atoms, or phenyl groups.

[0098] In some embodiments, L1 and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene.

[0099] Optionally, the substituents in L1 and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl or phenyl.

[0100] In some embodiments, L1 and L2 may be the same or different, and each is independently selected from the group consisting of single bonds or the following groups:

[0101] In some embodiments, L1 and L2 may be the same or different, and each is independently selected from the group consisting of single bonds or the following groups:

[0102] In some embodiments, one of R1 and R2 is selected from hydrogen or deuterium, and the other is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted biphenyl.

[0103] Optionally, the substituents in R1 and R2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl or trideuterated methyl.

[0104] In some embodiments, one of R1 and R2 is selected from hydrogen or deuterium, and the other is selected from the group consisting of:

[0105] In some embodiments, one of R1 and R2 is selected from hydrogen or deuterium, and the other is selected from the group consisting of:

[0106] In some embodiments, R1 is selected from hydrogen or deuterium, and R2 is selected from the group consisting of:

[0107] In some embodiments, R2 is selected from hydrogen or deuterium, and R1 is selected from the group consisting of:

[0108] In some embodiments, R3 and R4 may be the same or different, and each is independently selected from substituted or unsubstituted phenyl or substituted or unsubstituted naphthyl groups;

[0109] Optionally, the substituents in R3 and R4 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl or trideuterated methyl.

[0110] In some embodiments, R3 and R4 may be the same or different, and each is independently selected from the group consisting of:

[0111] In some embodiments, R3 and R4 may be the same or different, and each is independently selected from the group consisting of:

[0112] In some implementations, in Formula I Selected from the group consisting of the following structures:

[0113] In some implementations, in Formula I Selected from the group consisting of the following structures:

[0114] In some implementations, in Formula I Selected from the group consisting of the following structures:

[0115] In some implementations, in Formula I Selected from the group consisting of the following structures:

[0116] In some implementations, in Formula I Selected from the group consisting of the following structures:

[0117] In some implementations, in formula I, Selected from the group consisting of the following structures:

[0118] In some specific implementations... Selected from the group consisting of the following structures:

[0119] In some embodiments, the organic compound described in this application has the structure shown in Formula I-1 or Formula I-2:

[0120] The definitions of X, Y, L1, L2, R3, R4, R5, R6, R7, R8 and R9 are the same as in Equation I.

[0121] Specifically, the organic compounds represented by Formula I are selected from the group consisting of the following compounds.

[0122] In a second aspect, this application provides 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; the functional layer comprises the organic compound of this application.

[0123] Optionally, the functional layer includes a light-emitting adjustment layer, which contains the organic compounds of this application.

[0124] Optionally, the functional layer includes a light-emitting layer, a hole transport layer is provided between the light-emitting layer and the anode, and a first light-emitting adjustment layer and a second light-emitting adjustment layer are provided between the hole transport layer and the light-emitting layer; the first light-emitting adjustment layer is adjacent to the hole transport layer, and the second light-emitting adjustment layer is adjacent to the light-emitting layer; the first light-emitting adjustment layer contains the organic compound of this application.

[0125] In this application, the organic electroluminescent device can be a blue organic electroluminescent device, a red organic electroluminescent device, or a green organic electroluminescent device.

[0126] Optionally, the above-mentioned organic electroluminescent device is a green organic electroluminescent device.

[0127] In one embodiment, the organic electroluminescent device described in this application, as shown in FIG1, may include an anode 100, a hole injection layer 310, a hole transport layer 320, a first light-emitting adjustment layer 321, a second light-emitting adjustment layer 322, an organic light-emitting layer 330, a hole blocking layer 331, an electron transport layer 340, an electron injection layer 350, and a cathode 200 stacked together.

[0128] Optionally, the anode 100 comprises an anode material, preferably one with a high 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. Preferably, a transparent electrode comprising indium tin oxide (ITO) as the anode is included.

[0129] Optionally, the hole transport layer 320 may include one or more hole transport materials. The hole transport layer material may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. Specifically, it may be selected from the compounds shown below or any combination thereof, but is not limited thereto:

[0130] In one specific implementation, the hole transport layer 320 is HT-1.

[0131] In one specific embodiment, the first light-emitting adjustment layer 321 is an organic compound represented by Formula I of this application.

[0132] In one specific embodiment, the second light-emitting adjustment layer 322 is compound GP-1 or compound GP-2.

[0133] Optionally, the organic light-emitting layer 330 may be composed of a single light-emitting layer material, or it may 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. 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.

[0134] The host material of the organic light-emitting layer 330 can be a metal chelate compound, a bis(styrene) derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials; this application does not impose any special restrictions on this. The host material can be a single host material or a mixture of host materials. Specific examples of the host material include, but are not limited to:

[0135] In one specific embodiment, the main material of the organic light-emitting layer 330 is p-GH-1 and n-GH-1 composition.

[0136] The guest material of the organic light-emitting layer 330 can be selected with reference to existing technologies, such as iridium (III) organometallic complexes, platinum (II) organometallic complexes, ruthenium (II) complexes, etc. Specific examples of the guest material include, but are not limited to:

[0137] In one specific embodiment, the guest material of the organic light-emitting layer 330 is GD-1.

[0138] Optionally, the hole blocking layer 331 is a layer that blocks holes from reaching the cathode, and typically, it can be formed under the same conditions as the hole injection layer 310. Specifically, the hole blocking layer 331 includes oxadiazole derivatives or triazole derivatives, phenanthroline derivatives, aluminum complexes, etc., which are not specifically limited in this invention and are not limited thereto.

[0139] In some embodiments of the present invention, the hole blocking layer 331 is made of HB-1 composition.

[0140] Optionally, the electron transport layer 340 can be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials. The electron transport materials typically include metal complexes and / or nitrogen-containing heterocyclic derivatives. The metal complex material may be selected from, for example, LiQ, Alq3, etc.; the nitrogen-containing heterocyclic derivative may 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 Bphen, NBphen, ET-1, and BimiBphen, or anthracene compounds, triazine compounds, or pyrimidine compounds containing heteroazo aryl groups as shown below. Specific examples of nitrogen-containing heterocyclic derivatives used in electron transport materials include, but are not limited to:

[0141] In one specific embodiment, the electron transport layer 340 is composed of ET-1 and LiQ.

[0142] In this application, the cathode 200 may include a cathode material that has a small work function and facilitates electron injection into the functional layer. 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. Preferably, a metal electrode comprising magnesium and silver is included as the cathode.

[0143] Optionally, as shown in Figure 1, a hole injection layer 310 is further disposed between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320. The hole injection layer 310 can be selected from benzidine derivatives, starburst-like aryl amine compounds, phthalocyanine derivatives, or other materials; this application does not impose any special limitations on this. For example, the compounds contained in the hole injection layer 310 are selected from the group consisting of the following compounds:

[0144] In one specific embodiment, the hole injection layer 310 is composed of HT-1 and PD-1.

[0145] Optionally, as shown in Figure 1, an electron injection layer 350 is further disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic materials. For example, the electron injection layer 350 includes ytterbium (Yb).

[0146] Optionally, the cathode 200 may also have an organic coating layer. This application does not impose any special restrictions on this.

[0147] In one specific embodiment, the organic coating layer comprises compound CP-1.

[0148] Thirdly, this application provides an electronic device including the organic electroluminescent device provided in the second aspect of this application.

[0149] According to one embodiment, as shown in FIG2, the electronic device is a first electronic device 400, which includes the aforementioned organic electroluminescent device. The first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as, but not limited to, computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0150] The following examples illustrate the synthesis methods of the organic compounds described in this application, but this application is not limited in any way as a result.

[0151] Compounds synthesized using methods not mentioned in this application are all raw material products obtained through commercial means.

[0152] 1. Synthesis of intermediate IN-NH-x: taking IN-NH-1 as an example

[0153] Under nitrogen protection, 2-bromo-9,9-dimethylfluorene (114.0 g, 417.33 mmol), 3,4-diphenylaniline (107.5 g, 395.43 mmol), tris(dibenzylacetone)dipalladium (3.82 g, 4.17 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (3.98 g, 8.35 mmol), sodium tert-butoxide (60.15 g, 625.98 mmol), and toluene (950 mL) were added to a reaction flask. After the addition was complete, the mixture was stirred and heated to 108 °C for 4 h. The mixture was then cooled to room temperature, washed with water, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed from the filtrate under reduced pressure to obtain a yellow crude solid. The crude solid was then purified by recrystallization from toluene / petroleum ether to obtain intermediate IN-NH-1 (150.11 g, yield: 82.2%).

[0154] The IN-NH-x (IN-NH-2~IN-NH-21) in Table 1 were synthesized using the same method as IN-NH-1, with the difference that: raw material 1 was used instead of 2-bromo-9,9-dimethylfluorene, and raw material 2 was used instead of 3,4-diphenylaniline. The main raw materials used, the intermediates synthesized, and the yields are listed in Table 1.

[0155] Table 1

[0156] 2.1 Synthesis of intermediate IN-CP-y: Taking IN-CP-1 as an example

[0157] Under nitrogen protection, 2-chloro-6-bromobiphenyl (25.0 g, 93.44 mmol), 1-naphthylboronic acid (16.9 g, 98.26 mmol), tetra(triphenylphosphine)palladium (2.16 g, 1.87 mmol), tetrabutylammonium bromide (6.08 g, 18.87 mmol), potassium carbonate (28.41 g, 205.57 mmol), toluene (200 mL), ethanol (100 mL), and water (40 mL) were added to a reaction flask. After the addition was complete, stirring was started, and the mixture was heated to 70-75 °C and refluxed for 10 h. The reaction was stopped, cooled to room temperature, and extracted with dichloromethane. The organic phase was washed with water until neutral, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. The product was purified by recrystallization from toluene / petroleum ether and dried to give a white solid intermediate IN-CP-1 (23.3 g, yield: 79.2%).

[0158] IN-CP-y (IN-CP-2 to IN-CP-11) in Table 2 were synthesized using the same method as IN-CP-1, with the difference that: 2-chloro-6-bromo-biphenyl was replaced by raw material 3, and 1-naphthoic acid was replaced by raw material 4. The main raw materials used, the intermediates synthesized, and the yields are listed in Table 2.

[0159] Table 2

[0160] 2.2 Synthesis of intermediates IN-CP-12 and IN-CP-13:

[0161] Under nitrogen protection, 3,4-dibromochlorobenzene (15.0 g, 55.48 mmol) and 1-naphthoboric acid (20.0 g, 55.48 mmol) were added to the reaction flask. Then, equal amounts of tetra(triphenylphosphine)palladium (3.2 g, 2.77 mmol), tetrabutylammonium bromide (TBAB, 7.15 g, 22.19 mmol), potassium carbonate (30.67 g, 221.93 mmol), toluene (150 mL), ethanol (70 mL), and water (30 mL) were added to each of the two reaction flasks. After the additions were complete, the mixture was stirred and heated to 70-75 °C and refluxed for 12 h. The reaction was then stopped, cooled to room temperature, extracted with dichloromethane, and the organic phase was washed with water until neutral. The solution was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. The solution was purified by recrystallization from toluene / petroleum ether and dried to give a white solid intermediate IN-CP-12 (13.76 g, yield: 78.8%).

[0162] Intermediate IN-CP-13 was prepared using the same synthetic method as intermediate IN-CP-12, except that 2-naphthoboric acid was used instead of 1-naphthoboric acid, and all other conditions were exactly the same, to obtain a white solid intermediate IN-CP-13 (14.23 g, yield: 81.5%).

[0163] 3.1 Synthesis Example 1: Taking compound A1 as an example

[0164] Under nitrogen protection, intermediate IN-NH-1 (6.0 g, 13.71 mmol), compound Sub-DBP-1 (4.24 g, 13.71 mmol), tris(dibenzylacetone)dipalladium (0.13 g, 0.14 mmol), 2-dicyclohexylphosphine-2′,6′-dimethoxy-biphenyl (0.11 g, 0.27 mmol), sodium tert-butoxide (1.98 g, 20.57 mmol), and toluene (60 mL) were added to a reaction flask. After the addition was complete, the mixture was stirred and heated to 108 °C for 6 h. The mixture was then cooled to room temperature, washed with water, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed from the filtrate under reduced pressure to obtain a yellow crude solid. The crude solid was then purified by recrystallization from toluene / petroleum ether to obtain a white solid compound A1 (4.4 g, yield: 48.2%), mass spectrometry (m / z) = 666.3 [M+H]. + .

[0165] 3.2 Synthesis Example 2 to Synthesis Example 43:

[0166] The compounds listed in Table 3 were synthesized using the same method as compound A1, with the difference that reactant 5 was used instead of IN-NH-1, and reactant 6 was used instead of Sub-DBP-1. The main reactants used, the structures of the product compounds, the yield of the final step, and their mass spectra are listed in Table 3.

[0167] Table 3

[0168] 4. NMR data for some compounds are shown in Table 4:

[0169] Table 4

[0170] Fabrication and evaluation of organic electroluminescent devices

[0171] Example 1: Green Organic Electroluminescent Device

[0172] The anode is prepared through the following process: [The anode thickness is...] On the ITO / Ag / ITO experimental substrate, surface treatment was performed using ultraviolet light, ozone, and O2:N2 plasma to increase the work function of the anode, and the surface of the experimental substrate was cleaned with organic solvents to remove impurities and oil stains.

[0173] On the anode substrate, compounds HT-1 and PD-1 were co-deposited at a deposition rate ratio of 97%:3% to form a layer with a thickness of [missing information]. Hole injection layer.

[0174] Compound HT-1 was deposited on the hole injection layer to form a thickness of [thickness value missing]. The hole transport layer.

[0175] Compound A1 was deposited on the hole transport layer to form a thickness of [missing information]. The first luminescence adjustment layer.

[0176] Compound GP-1 is deposited on the first light-emitting adjustment layer to form a layer with a thickness of [missing information]. The second light-emitting adjustment layer.

[0177] On the second luminescent adjustment layer, compounds p-GH-1, n-GH-1, and GD-1 were co-deposited at a deposition rate ratio of 65%:35%:10% to form a layer with a thickness of [missing information]. The organic light-emitting layer.

[0178] Chemical HB-1 was deposited onto the organic light-emitting layer to form a layer with a thickness of [missing information]. Hole-blocking layer.

[0179] On the hole-blocking layer, compounds ET-1 and LiQ were co-deposited at a 50%:50% evaporation rate ratio to form a layer with a thickness of [missing information]. The electron transport layer.

[0180] Ytterbium (Yb) is deposited on the electron transport layer to form a thickness of [missing information]. The electron injection layer.

[0181] On the electron-injected layer, magnesium (Mg) and silver (Ag) are co-deposited at a deposition rate of 10%:90% to form a layer with a thickness of [thickness value missing]. The cathode.

[0182] Finally, compound CP-1 is deposited on the cathode to form a thickness of [thickness value missing]. The organic coating layer is used to complete the fabrication of green organic electroluminescent devices.

[0183] Examples 2 to 86:

[0184] Organic electroluminescent devices were prepared using the same method as in Example 1, except that: when preparing the first luminescence adjustment layer, the compound A1 in Example 1 was replaced with the first luminescence adjustment layer material in Table 5; and when preparing the second luminescence adjustment layer, the compound GP-1 in Example 1 was replaced with the second red light adjustment layer material in Table 5.

[0185] Comparative Examples 1 to 10:

[0186] Organic electroluminescent devices were prepared using the same method as in Example 1, except that: when preparing the first luminescence adjustment layer, the compound A1 in Example 1 was replaced with the first luminescence adjustment layer material in Table 5; and when preparing the second luminescence adjustment layer, the compound GP-1 in Example 1 was replaced with the second red light adjustment layer material in Table 5.

[0187] In the fabrication of organic electroluminescent devices, the structures of the various materials used in the comparative and examples are as follows:

[0188] The performance of the green organic electroluminescent devices prepared in Examples 1-86 and Comparative Examples 1-10 was tested, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the condition of 20 mA / cm. 2 The lifetime of the T95 device was tested under the following conditions, and the test results are shown in Table 5 below.

[0189] Table 5

[0190] As can be seen from Table 5 above, compared with the organic electroluminescent devices of Comparative Examples 1 to 10, the organic electroluminescent devices of Examples 1 to 86 have significantly improved performance, mainly manifested in the following: the operating voltage of the device is reduced by at least 0.13V, the current efficiency is increased by at least 14.6%, and the T95 lifetime is increased by at least 17.6%.

[0191] The reason for this may be that, compared to comparative compounds A, C, D, and E, the compounds of this application contain 3,4-disubstituted phenyl groups (phenyl and / or naphthyl groups) linked to a central N atom to form aromatic amine compounds. These compounds have deeper HOMO levels, shallower LUMO levels, and a larger band gap (Eg), allowing the molecules to effectively block electrons and recombine excitons, thereby improving device efficiency and lifetime. Compared to compound B, the disubstituted phenyl groups in the compounds of this application are all small-volume aryl groups, such as phenyl, naphthyl, or biphenyl, avoiding higher molecular weight, more substituted phenyl configurations. This avoids excessively high evaporation temperatures, resulting in better thermal stability during device fabrication and significantly improved device performance.

[0192] 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.

Claims

1. An organic compound, characterized in that, The organic compound has the structure shown in Formula I: Where X and Y are the same or different, and each is independently selected from single bonds, C(R) ... a R b ), N(R c ), O, S, C(R) d () or N; and X and Y are not both single bonds; R a R b R c and R d They may be the same or different, and each is independently selected from substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 40 carbon atoms; Optional, R a and R b Forming 3- to 15-member saturated or unsaturated rings; R a R b R c and R d The substituents in the group 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, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, deuterated heteroaryl with 3 to 20 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, or triarylsilyl with 18 to 24 carbon atoms; L1 and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 12 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms; The substituents in L1 and L2 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, aryl with 6 to 10 carbon atoms, and heteroaryl with 3 to 12 carbon atoms. One of R1 and R2 is selected from hydrogen or deuterium, and the other is selected from substituted or unsubstituted aryl groups with 6 to 12 carbon atoms; R3 and R4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 10 carbon atoms; The substituents in R1, R2, R3 and R4 may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, and haloalkyl with 1 to 5 carbon atoms. Each of R5, R6, R7, R8 and R9 may be the same or different, and each is independently selected from hydrogen, deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, and haloalkyl with 1 to 10 carbon atoms. a is the number of R5s, and a is selected from 1 or 2. When a is greater than 1, any two R5s are the same or different. b is the number of R6s, and b is selected from 1, 2, 3, 4 or 5. When b is greater than 1, any two R6s are the same or different. c is the number of R7s, and c is selected from 1, 2 or 3. When c is greater than 1, any two R7s are the same or different. d is the number of R8s, which can be selected from 1, 2 or 3. When d is greater than 1, any two R8s are the same or different. Optionally, any two adjacent R8s form a 3 to 15-element saturated or unsaturated ring. e is the number of R9s, which can be selected from 1, 2, 3 or 4. When e is greater than 1, any two R9s can be the same or different. Optionally, any two adjacent R9s can form a 3 to 15-element saturated or unsaturated ring.

2. The organic compound according to claim 1, characterized in that, R a R b R c and R d They may be the same or different, and each is independently selected from substituted or unsubstituted alkyl groups having 1 to 5 carbon atoms, or substituted or unsubstituted aryl groups having 6 to 18 carbon atoms; Optional, R a and R b Forming 5- to 14-member saturated or unsaturated rings; R a R b R c and R d The substituents in the group are the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl group with 1 to 5 carbon atoms, haloalkyl group with 1 to 5 carbon atoms, deuteralkyl group with 1 to 5 carbon atoms, or trimethylsilyl group; Optionally, L1 and L2 may be the same or different, and each may be independently selected from single bonds or substituted or unsubstituted aryl groups having 6 to 12 carbon atoms; The substituents in L1 and L2 may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, or phenyl. Optionally, each of R5, R6, R7, R8 and R9 may be the same or different, and each may be independently selected from hydrogen, deuterium, halogen group, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, and deuteralkyl with 1 to 5 carbon atoms. Optionally, any two adjacent R8s can form a 5- to 10-element saturated or unsaturated ring; Optionally, any two adjacent R9s can form a 5- to 10-element saturated or unsaturated ring.

3. The organic compound according to claim 1, characterized in that, R a R b R c and R d They may be the same or different, and each is independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, phenyl, naphthyl, biphenyl, terphenyl, pentadeuterated phenyl or heptadeuterated naphthyl; Optional, R a and R b It can form cyclopentane, cyclohexane, adamantane, fluorene ring, oxanthracene ring, or thionthanene ring; Optionally, each of R5, R6, R7, R8 and R9 may be the same or different, and each may be independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, trifluoromethyl, and trideuterated methyl. Optionally, any two adjacent R8s can form a benzene ring; Optionally, any two adjacent R9s can form a benzene ring.

4. The organic compound according to claim 1, characterized in that, In Formula I Selected from the group consisting of the following groups:

5. The organic compound according to claim 1, characterized in that, L1 and L2 may be the same or different, and each is independently selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene; The substituents in L1 and L2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl or phenyl; Optionally, L1 and L2 may be the same or different, and each may be independently selected from the group consisting of single bonds or the following groups:

6. The organic compound according to claim 1, characterized in that, One of R1 and R2 is selected from hydrogen or deuterium, and the other is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl or substituted or unsubstituted biphenyl. The substituents in R1 and R2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl or trideuterated methyl; Optionally, R3 and R4 may be the same or different, and each may be independently selected from substituted or unsubstituted phenyl or substituted or unsubstituted naphthyl groups; The substituents in R3 and R4 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl or trideuterated methyl.

7. The organic compound according to claim 1, characterized in that, One of R1 and R2 is selected from hydrogen or deuterium, and the other is selected from the group consisting of the following groups: Alternatively, R3 and R4 may be the same or different, and each may be independently selected from the group consisting of:

8. The organic compound according to claim 1, characterized in that, In Formula I Selected from the group consisting of the following structures: Optionally, in Equation I Selected from the group consisting of the following structures:

9. The organic compound according to claim 1, characterized in that, In Formula I Selected from the group consisting of the following structures:

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 the organic compound according to any one of claims 1 to 10.

12. The organic electroluminescent device according to claim 11, characterized in that, The functional layer includes a light-emitting adjustment layer, which contains the aforementioned organic compound.

13. The organic electroluminescent device according to claim 11, characterized in that, The functional layer includes an organic light-emitting layer, a hole transport layer is provided between the organic light-emitting layer and the anode, and a first light-emitting adjustment layer and a second light-emitting adjustment layer are provided between the hole transport layer and the organic light-emitting layer; the first light-emitting adjustment layer is adjacent to the hole transport layer, and the second light-emitting adjustment layer is adjacent to the organic light-emitting layer; the first light-emitting adjustment layer contains the organic compound.

14. An electronic device comprising the organic electroluminescent device according to any one of claims 11 to 13.

Images