Organic compounds, organic electroluminescent devices and electronic devices

Abstract

This application belongs to the technical field of organic electroluminescent materials, and provides an organic compound with the structure shown in Formula 1. This application also provides organic electroluminescent devices and electronic devices comprising this organic compound. As a light-emitting modulating layer material, this organic compound can effectively enhance device efficiency and improve device lifespan.

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 emission (OLED) typically refers to the conversion of electrical energy into light energy using organic materials. Organic electronic devices utilizing OLEDs generally have a structure comprising an anode and a cathode, and layers of organic materials between them. These organic material layers are usually multilayered structures composed of different materials to improve the efficiency and stability of the organic electronic devices. Examples include hole injection layers, hole transport layers, light-emitting layers, electron transport layers, and electron injection layers. Materials used as organic layers in organic electronic devices can be categorized into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials. Based on their function, lifetime and efficiency are the biggest challenges for organic light-emitting diodes (OLEDs). As displays become increasingly larger, these efficiency and lifetime issues must be addressed. Currently, although many high-performance organic electroluminescent materials have been developed, the technology still faces many challenges, requiring further exploration and development of materials with even better performance. Summary of the Invention

[0003] The purpose of this application is to overcome the shortcomings of the prior art and provide an organic compound and an organic electroluminescent device and electronic device containing the same, wherein the organic compound can enhance device efficiency and lifespan.

[0004] The first aspect of this application provides an organic compound having the structure shown in Formula 1:

[0005]

[0006] Where X is selected from O, N, N(R) or S;

[0007] R is selected from alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, deuterated aryl groups having 6 to 20 carbon atoms, or deuterated heteroaryl groups having 3 to 20 carbon atoms.

[0008] L, 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 40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms.

[0009] Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 40 carbon atoms or substituted or unsubstituted heteroaryl groups having 3 to 40 carbon atoms;

[0010] The substituents in L, L1, L2, Ar1, and Ar2 may be the same or different from each other, 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, trialkylsilyl with 3 to 12 carbon atoms, or triarylsilyl with 18 to 24 carbon atoms;

[0011] Each R m and R n They may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, 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 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, deuterated aryl groups having 6 to 20 carbon atoms, or deuterated heteroaryl groups having 3 to 20 carbon atoms;

[0012] m is R m The number of elements, m is selected from 0, 1, 2, 3, 4 or 5;

[0013] n is R n The number of elements, n, is selected from 0, 1, 2, or 3.

[0014] A second aspect of this application provides an organic electroluminescent device, the organic electroluminescent device comprising an anode, a cathode, and at least one functional layer disposed between the anode and the cathode, the functional layer comprising the organic compound described in the first aspect of this application.

[0015] A third aspect of this application provides an electronic device, which includes the organic electroluminescent device described in the second aspect of this application.

[0016] The organic compound of this application has a core structure consisting of a heteroatom-containing polycyclic fused aryl-adamantyl alkyl group. Among them, the adamantyl group is an electron-rich group. The adamantyl group, after being fused with a heteroatom-containing polycyclic fused aryl group, forms a large conjugated planar structure with high electron cloud density. This core structure, when connected to the aromatic amino group, constitutes a core structure with high hole mobility. On the other hand, the fusion of the conjugated planar polycyclic aromatic group with the sterically hindered adamantyl group increases the overall spatial density of the molecule, effectively reducing intermolecular stacking. When using this material to fabricate OLED devices, it can effectively improve the amorphous morphology during film formation, resulting in better device stability. Specifically, the organic compound of this application, when used as a light-emitting adjustment layer material for organic electroluminescent devices, can effectively enhance device efficiency and improve device lifespan.

[0017] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description

[0018] The accompanying drawings, which are incorporated in and form part of this specification, illustrate embodiments consistent with this application and, together with the description, serve to explain the principles of this application.

[0019] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.

[0020] Figure 2 This is a schematic diagram of the structure of an electronic device according to one embodiment of this application.

[0021] Explanation of reference numerals in the attached figures

[0022] 100, Anode; 200, Cathode; 300, Functional layer; 310, Hole injection layer; 321, Hole transport layer; 322, Light emission adjustment layer; 330, Organic light emission layer; 340, Electron transport layer; 350, Electron injection layer; 400, Electronic device. Detailed Implementation

[0023] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, these exemplary embodiments can be implemented in many forms and should not be construed as limited to the examples set forth herein; rather, they are provided so that this application will be more comprehensive and complete, and will fully convey the concept of the exemplary embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a full understanding of embodiments of this application.

[0024] The first aspect of this application provides an organic compound having the structure shown in Formula 1:

[0025]

[0026]

[0027] Where X is selected from O, N, N(R) or S;

[0028] R is selected from alkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, deuterated aryl groups having 6 to 20 carbon atoms, or deuterated heteroaryl groups having 3 to 20 carbon atoms.

[0029] L, 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 40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms.

[0030] Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 40 carbon atoms or substituted or unsubstituted heteroaryl groups having 3 to 40 carbon atoms;

[0031] The substituents in L, L1, L2, Ar1, and Ar2 may be the same or different from each other, 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, trialkylsilyl with 3 to 12 carbon atoms, or triarylsilyl with 18 to 24 carbon atoms;

[0032] Each R m and R n They may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, 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 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, deuterated aryl groups having 6 to 20 carbon atoms, or deuterated heteroaryl groups having 3 to 20 carbon atoms;

[0033] m is R m The number of elements, m is selected from 0, 1, 2, 3, 4 or 5;

[0034] n is R n The number of elements, n, is selected from 0, 1, 2, or 3.

[0035] In this application, the descriptive phrases "each...independently is," "...each independently is," and "...independently selected from" are interchangeable and should be interpreted broadly. They can mean either that the specific options expressed by the same symbol in different groups do not affect each other, or that the specific options expressed by the same symbol in the same group do not affect each other. For example, " In this formula, each q is independently 0, 1, 2 or 3, and each R is independently selected from hydrogen, deuterium, fluorine or chlorine. The meaning is as follows: Formula Q-1 indicates that there are q substituents R on the benzene ring. Each R can be the same or different, and the options of each R do not affect each other. Formula Q-2 indicates that there are q substituents R on each benzene ring of biphenyl. The number q of substituents R on the two benzene rings can be the same or different, and each R can be the same or different. The options of each R do not affect each other.

[0036] 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 Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an unsubstituted aryl group. The aforementioned substituents, i.e., Rc, can be, for example, deuterium, halogen groups, cyano, heteroaryl, deuterated heteroaryl, aryl, deuterated aryl, trialkylsilyl, triarylsilyl, alkyl, deuterated alkyl, haloalkyl, cycloalkyl, etc. The number of substituents can be one or more. In this application, a non-orienting linker 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.

[0037] 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).

[0038]

[0039] 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.

[0040]

[0041] 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).

[0042]

[0043] In this application, L, L1, L2, Ar1, Ar2, R, R m R n The number of carbon atoms refers to the total number of carbon atoms. For example, if L1 is selected from a substituted arylene with 12 carbon atoms, then the arylene and its substituents have a total of 12 carbon atoms.

[0044] In this application, "alkyl" can include straight-chain alkyl or branched alkyl. An alkyl group may have 1 to 10 carbon atoms. In this application, numerical ranges such as "1 to 10" refer to integers within a given range; for example, "1 to 10 carbon atoms" means an alkyl group that may contain 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms. Optionally, the alkyl group is selected from alkyl groups having 1 to 5 carbon atoms, including but not limited to methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and pentyl.

[0045] In this application, cycloalkyl refers to a group derived from a saturated cyclic carbon chain structure. A cycloalkyl group may have 3 to 10 carbon atoms; in this application, numerical ranges such as "3 to 10" refer to integers within a given range; for example, "5 to 10 carbon atoms" means that it may contain 5, 6, 7, 8, 9, or 10 carbon atoms. Optionally, specific embodiments of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, norbornyl, etc.

[0046] 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, fluorenyl, 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, anthracene, phenanthrene, biphenyl, terphenyl, perylene, pyrene, benzofluoranthyl, etc. 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, etc. In this application, biphenyl can be understood as a phenyl-substituted aryl group or an unsubstituted aryl group.

[0047] In this application, the term arylene refers to a divalent group formed by the further loss of a hydrogen atom from an aryl group.

[0048] 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 atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, a triarylsilyl group, an alkyl group, a cycloalkyl group, a haloalkyl group, a deuterated alkyl group, a deuterated aryl group, or a deuterated heteroaryl group. It is understood that the number of carbon atoms in the substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on it. For example, Ar1 is... Therefore, it has 7 carbon atoms.

[0049] In this application, aryl groups used as substituents include, but are not limited to, phenyl, naphthyl, and biphenyl groups.

[0050] 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.

[0051] In this application, terphenyl includes

[0052] In this application, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5, or 6 heteroatoms, wherein the heteroatoms can be at least one of B, O, N, P, Si, Se, and S. A heteroaryl group can be a monocyclic or polycyclic heteroaryl group; in other words, a heteroaryl group can be a single aromatic ring system or a system of multiple aromatic rings linked by carbon-carbon bonds, and any aromatic ring system can be a single aromatic monocyclic ring or a fused aromatic ring. For example, a heteroaryl group may include thiophene, furanyl, pyrroleyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxolinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolinyl, indolyl, carbazole, benzoxazolyl, and benzimidazole. The group includes, but is not limited to, benzothiazolyl, benzocarbazolyl, benzothiophenel, dibenzothiophenel, thienozothiophenel, benzofuranyl, phenanthrolinel, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silanyl, dibenzofuranyl, and N-arylcarbazolyl (such as N-phenylcarbazolyl), N-heteroarylcarbazolyl (such as N-pyridylcarbazolyl), and N-alkylcarbazolyl (such as N-methylcarbazolyl), etc. Among these, thiophenel, furanyl, and phenanthrolinel are heteroaryl groups of the single aromatic ring type, while N-arylcarbazolyl (such as N-phenylcarbazolyl) and N-heteroarylcarbazolyl are heteroaryl groups of the polycyclic system type linked by carbon-carbon conjugation. For example, in this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl group 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.

[0053] In this application, the term "hybrid aryl" refers to a divalent group formed by the further loss of a hydrogen atom from a heteroaryl group.

[0054] In this application, the substituted heteroaryl group may be one or more hydrogen atoms of the heteroaryl group that are replaced by groups such as deuterium atom, halogen group, cyano, aryl, heteroaryl, trialkylsilyl, triarylsilyl, alkyl, cycloalkyl, haloalkyl, deuterated alkyl, deuterated aryl, deuterated heteroaryl, etc.

[0055] 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.

[0056] In this application, the heteroaryl group used as a substituent includes, but is not limited to, dibenzofuranyl, dibenzothiophenyl, carbazoyl, N-phenylcarbazoyl, etc.

[0057] 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 a compound or group in which one, more or all of the available hydrogens have been replaced by deuterium.

[0058] In this application, the halogen group can be fluorine, chlorine, bromine, or iodine.

[0059] In this application, a deuterated aryl group can be one or more hydrogen atoms of an aryl group that are replaced by deuterium. Specific examples of deuterated aryl groups include, but are not limited to, pentadeuterated phenyl and heptadeuterated naphthyl.

[0060] In this application, the 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.

[0061] In this application, a haloalkyl group may be an alkyl group in which one or more hydrogen atoms are replaced by halogen atoms. Specific examples of haloalkyl groups include, but are not limited to, trifluoromethyl.

[0062] 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.

[0063] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl groups.

[0064] In this application, specific examples of triarylsilyl groups include, but are not limited to, triphenylsilyl groups.

[0065] In the application, the square brackets “[]” in Formula 1 indicate that group L can be attached to the structure Any substituted site in the matrix, i.e., L can be attached to... At any position shown in 1, 2, 3, 4, 5, 6, 7, 8, 9, when X is selected from N, It is attached to the N atom at position 9.

[0066] In some embodiments of this application, the organic compound shown in Formula 1 is selected from the structures shown in Formula 1-1, Formula 1-2, Formula 1-3, Formula 1-4, Formula 1-5, Formula 1-6, Formula 1-7, Formula 1-8, or Formula 1-9:

[0067]

[0068]

[0069] Among them, L, L1, L2, Ar1, Ar2, R, R m R nThe definitions of , m, and n are the same as in Equation 1.

[0070] In some embodiments of this application, L, 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 18 carbon atoms, or substituted or unsubstituted heteroaryl groups with 12 to 18 carbon atoms.

[0071] For example, L, L1, and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms, or substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17, or 18 carbon atoms.

[0072] Optionally, the substituents in L, L1, and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, 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 12 carbon atoms, heteroaryl with 5 to 12 carbon atoms, or trialkylsilyl with 3 to 9 carbon atoms.

[0073] In some embodiments of this application, L, 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, substituted or unsubstituted phenanthylene, substituted or unsubstituted anthraceneylene, substituted or unsubstituted fluoreneylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiopheneylene, or substituted or unsubstituted carbazolylene.

[0074] Optionally, the substituents in L, L1 and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, trimethylsilyl or phenyl.

[0075] In some embodiments of this application, L, 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:

[0076]

[0077] In some embodiments of this application, L, 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:

[0078]

[0079] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms or substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms.

[0080] For example, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 carbon atoms, or substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0081] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, aryl with 6 to 12 carbon atoms, heteroaryl with 5 to 12 carbon atoms, trialkylsilyl or triphenylsilyl with 3 to 9 carbon atoms.

[0082] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthrayl, substituted or unsubstituted pyrene, substituted or unsubstituted triphenylene, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, or substituted or unsubstituted carbazoleyl.

[0083] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, cyclopentane, cyclohexane, phenyl, naphthyl, trimethylsilyl, or triphenylsilyl.

[0084] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and each is independently selected from the following groups:

[0085]

[0086] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and each is independently selected from the group consisting of:

[0087]

[0088]

[0089]

[0090] In some embodiments of this application, R is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, carbazoleyl, pentadeuterated phenyl, or heptadeuterated naphthyl.

[0091] In some embodiments of this application, each R m and R n They may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, trideuterated methyl, trifluoromethyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophene, carbazole, pentadeuterated phenyl, or heptadeuterated naphthyl.

[0092] Specifically, the organic compound may be selected from the group consisting of the following compounds:

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109] A second aspect of this application provides an organic electroluminescent device, the organic electroluminescent device comprising an anode, a cathode, and a functional layer disposed between the cathode and the anode, the functional layer comprising the organic compound described in the first aspect of this application.

[0110] In this application, the organic electroluminescent device may be a blue organic electroluminescent device, a red organic electroluminescent device, or a green organic electroluminescent device.

[0111] Alternatively, the organic electroluminescent device may be a red organic electroluminescent device.

[0112] Optionally, the functional layer includes a light-emitting adjustment layer, which contains the organic compounds of this application.

[0113] In one specific implementation, such as Figure 1 As shown, the organic electroluminescent device described in this application may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200. Specifically, the organic electroluminescent device may include an anode 100, a hole transport layer 321, a light emission adjustment layer 322, an organic light emission layer 330, an electron transport layer 340 and a cathode 200 disposed in sequence.

[0114] Optionally, the anode 100 comprises the following anode materials, preferably materials with a large work function that facilitate hole injection into the functional layer. Anode materials specifically include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al and SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode comprises indium tin oxide (ITO) as the anode.

[0115] Optionally, the hole transport layer 321 may include one or more hole transport materials, which may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. For example, the material of the hole transport layer is selected from the group consisting of the following compounds:

[0116]

[0117]

[0118] In one specific embodiment, the hole transport layer 321 is composed of HT-1.

[0119] In this application, the luminescent adjustment layer 322 may include one or more materials, which may be selected from carbazole polymers or other types of compounds, and this application does not impose specific limitations.

[0120] In one specific embodiment, the light-emitting adjustment layer 322 is composed of organic compounds of this application.

[0121] Optionally, the organic light-emitting layer 330 can be composed of a single light-emitting material, or it can be composed of a host material and a guest material. Preferably, 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.

[0122] 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. The host material can be a single host material or a mixture of host materials.

[0123] In one specific embodiment, the host material of the organic light-emitting layer is composed of compound RH-N1. With compound RH-P1 Together they form a whole.

[0124] 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:

[0125]

[0126]

[0127] In one specific embodiment, the guest material is composed of compound RD-1.

[0128] 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 contain metal complexes or / or nitrogen-containing heterocyclic derivatives. The metal complexes may be selected from, for example, LiQ, Alq3, etc. The nitrogen-containing heterocyclic derivatives may be aromatic rings with a nitrogen-containing six- or five-membered ring skeleton, fused aromatic ring compounds with a nitrogen-containing six- 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 heteroazoyl groups as shown below. Specific examples of the nitrogen-containing heterocyclic derivatives used for the electron transport materials include, but are not limited to:

[0129]

[0130] In one specific embodiment, the electron transport layer 340 is composed of the compound LiQ and the compound ET-1.

[0131] Optionally, the cathode 200 includes a cathode material that has a small work function and facilitates electron injection into the functional layer. Specifically, examples of cathode materials include, but are not limited to: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca, but are not limited thereto. Preferably, a metal electrode containing silver and magnesium is used as the cathode.

[0132] Optionally, such as Figure 1 As shown, a hole injection layer 310 may also be disposed between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 may be selected from benzidine derivatives, starburst-like aryl amine compounds, phthalocyanine derivatives, or other materials; this application does not impose any special limitations on this. For example, the compounds contained in the hole injection layer 310 may be selected from the group consisting of the following compounds:

[0133]

[0134] In one specific embodiment, the hole injection layer 310 may be composed of compound PD-1 and compound HT-1.

[0135] Optionally, such as Figure 1As shown, an electron injection layer 350 may also be disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 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.

[0136] In one specific embodiment, the electron injection layer 350 includes ytterbium (Yb).

[0137] Optionally, the cathode 200 also has a cathode protection layer.

[0138] In one specific embodiment, the cathode protection layer comprises compound CP-1.

[0139] A third aspect of this application provides an electronic device including the organic electroluminescent device provided in the second aspect of this application.

[0140] According to one implementation method, such as Figure 2 As shown, the electronic device is electronic device 400, which includes the aforementioned organic electroluminescent device. Electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as, but not limited to, computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0141] The following examples illustrate the synthesis method of the organic compounds of this application, but this application is not limited thereto.

[0142] Compounds synthesized using methods not mentioned in this application are all raw material products obtained through commercial means.

[0143] Synthesis example

[0144] 1. Synthesis of intermediate IM a1-1:

[0145]

[0146] (1) 1-Bromo-5-chloro-3-fluoro-2-iodobenzene (40.00 g, 119.28 mmol), 2-hydroxy-1-naphthoic acid (22.42 g, 119.28 mmol), potassium carbonate (K2CO3, 32.97 g, 238.56 mmol), tetrabutylammonium bromide (TBAB, 3.85 g, 11.93 mmol), toluene (PhMe, 240 mL), ethanol (EtOH, 80 mL) and deionized water (80 mL) were added to a three-necked flask and stirred for 15 min under nitrogen protection. Tetra(triphenylphosphine)palladium (Pd(PPh3)4, 1.38 g, 1.19 mmol) was added and the temperature was raised to 75 °C to 80 °C. The mixture was stirred for 20 h. After the reaction was completed, the reaction solution was cooled to room temperature, washed with water several times until neutral, and dried with anhydrous magnesium sulfate. The organic phase was depressurized to remove the solvent, and then washed with ethanol to obtain a white solid IM a1-a1 (25.60 g, yield: 61.04%).

[0147]

[0148] (2) IM a1-a1 (25.00 g, 71.10 mmol) and N,N-dimethylformamide (250 mL) were added to a three-necked flask. Stirring was started under nitrogen protection. After the system was dissolved, cesium carbonate (23.17 g, 71.10 mmol) was added, and the mixture was heated to 140℃~150℃ and reacted for 5 h. After the reaction was complete, the reaction solution was cooled to room temperature and extracted with dichloromethane and water. The extracted organic phase was washed with water until neutral and then dried with anhydrous magnesium sulfate. The solvent was removed from the dried organic phase under reduced pressure to obtain the crude product. The crude product was then crystallized with dichloromethane / anhydrous ethanol to obtain IM a1-b1 (20.80 g, yield: 88.22%).

[0149]

[0150] (3) IM a1-b1 (20.00 g, 60.32 mmol) and THF (120 mL) were added to a 500 mL three-necked flask and cooled to -90 °C to -78 °C. A tetrahydrofuran solution of n-butyllithium (60.32 mmol) (2 mol / L, 30.16 mL) was added dropwise, and the mixture was reacted at -90 °C to -78 °C for 1 h. Adamantone (9.06 g, 60.32 mmol) was dissolved in THF (36 mL) and slowly added dropwise to the reaction system. The mixture was reacted at -78 °C to -90 °C for 1 h, then allowed to rise naturally to room temperature and stirred for 6 h. Water (200 mL) was added to the reaction system to terminate the reaction. The reaction mixture was extracted with ethyl acetate and water. The organic layer obtained from the extraction was concentrated under reduced pressure to obtain a crude product. The crude product was crystallized with dichloromethane / n-heptane to obtain IM a1-c1 (14.20 g, yield: 58.43%).

[0151]

[0152] (4) IM a1-c1 (14.00 g, 34.75 mmol) was placed in a 250 mL round-bottom flask with glacial acetic acid (140 mL) and sulfuric acid (98 wt%, 1.02 mL). The mixture was heated to 75 °C and reacted for 4 h, during which a solid precipitated. After the reaction was complete, the system was cooled to room temperature and filtered. The filter cake was washed repeatedly with water and ethanol to obtain a crude product. The crude product was then crystallized with dichloromethane / n-heptane to obtain IM a1-1 (11.95 g, yield: 89.35%).

[0153] IM a1-X (X is 2 to 11) in Table 1 were prepared using the same method as IM a1-1, except that 1-bromo-5-chloro-3-fluoro-2-iodobenzene in step (1) was replaced by raw material 1, and 2-hydroxy-1-naphthoic acid in step (1) was replaced by raw material 2. The main raw materials used, the intermediates synthesized and their yields in the final step are listed in Table 1.

[0154] Table 1

[0155]

[0156]

[0157]

[0158] 2. Synthesis of intermediate IM a2-1:

[0159]

[0160] (1) IM a1-1 (5.00 g, 12.99 mmol), pinacol diborate (3.30 g, 12.99 mmol), tris(dibenzylacetone)palladium (0.12 g, 0.13 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.62 g, 1.30 mmol), potassium acetate (2.55 g, 25.98 mmol), and 1,4-dioxane (60 mL) were added to a three-necked round-bottom flask. The mixture was heated to 80 °C under nitrogen protection and stirred for 4 h. After cooling to room temperature, the reaction solution was washed with water, dried with magnesium sulfate, filtered, and the solvent was removed from the filtrate under reduced pressure. The crude product was purified by recrystallization using a toluene system to obtain solid IM a2-a1 (4.50 g, yield: 72.71%).

[0161]

[0162] (2) IM a2-a1 (4.00 g, 8.40 mmol), 4-chlorobromobenzene (1.61 g, 8.40 mmol), potassium carbonate (2.32 g, 16.79 mmol), tetrabutylammonium bromide (0.27 g, 0.84 mmol), toluene (24 mL), ethanol (8 mL), and deionized water (8 mL) were added to a three-necked flask. The mixture was stirred for 15 min under nitrogen protection, then tetra(triphenylphosphine)palladium (0.10 g, 0.08 mmol) was added, and the temperature was raised to 75 °C–80 °C. The mixture was stirred for 6 h. The reaction solution was cooled to room temperature and washed several times with water until neutral. Then, it was dried using anhydrous magnesium sulfate. The solvent was removed from the dried organic phase under reduced pressure, and the solution was recrystallized from dichloromethane / n-heptane to obtain a white solid IMa2-1 (2.52 g, yield: 65.10%).

[0163] IM a2-Y (Y is 2 to 6) in Table 2 was prepared using the same method as IM a2-1, except that IM a1-1 in step (1) was replaced by raw material 3, and 4-chlorobromobenzene in step (2) was replaced by raw material 4. The main raw materials used, the intermediates synthesized and their yields in the final step are listed in Table 2.

[0164] Table 2

[0165]

[0166]

[0167] 3. Synthesis Example 1: Synthesis of Compound 73:

[0168]

[0169] IM a1-1 (5.00 g, 12.99 mmol), di(4-biphenyl)amine (4.18 g, 12.99 mmol), tris(dibenzylacetone)dipalladium (0.12 g, 0.13 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.11 g, 0.26 mmol), and sodium tert-butoxide (1.87 g, 19.49 mmol) were added to toluene (50 mL). The mixture was heated to 108 °C under nitrogen protection and stirred for 3 h. After cooling to room temperature, the reaction solution was washed with water and separated. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed from the filtrate under reduced pressure. The crude product was purified by recrystallization from toluene to give a white solid compound 73 (5.80 g, yield: 66.65%). Mass spectrometry (m / z) = 670.3 [M+H] + .

[0170] Compound X in Table 3 was prepared using the same method as compound 73, except that starting material 5 was used instead of IM a1-1 and starting material 6 was used instead of di(4-biphenyl)amine. The main starting materials used, the synthesized compounds, their yields, and mass spectra are listed in Table 3.

[0171] Table 3

[0172]

[0173]

[0174]

[0175]

[0176]

[0177] The NMR data of some compounds are shown in Table 4 below:

[0178] Table 4

[0179]

[0180]

[0181] Fabrication and evaluation of organic electroluminescent devices

[0182] Example 1: Fabrication of a red organic electroluminescent device

[0183] 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.

[0184] On the anode substrate, compounds HT-1 and PD-1 were co-deposited at a deposition rate ratio of 98%:2% to form a layer with a thickness of [missing information]. Hole injection layer.

[0185] Compound HT-1 was deposited on the hole injection layer to form a thickness of [thickness value missing]. The hole transport layer.

[0186] Compound 73 is deposited on the hole transport layer to form a thickness of The light-emitting adjustment layer.

[0187] On the light-emitting adjustment layer, compounds RH-N1, RH-P1, and RD-1 were co-deposited at a deposition rate ratio of 55%:45%:2% to form a layer with a thickness of [missing information]. The red light-emitting layer.

[0188] On the red light-emitting layer, compounds ET-1 and LiQ were co-deposited at a 50%:50% deposition rate to form a layer with a thickness of [missing information]. The electron transport layer.

[0189] Yb is deposited on the electron transport layer to form a thickness of An electron-injected layer is formed. Magnesium (Mg) and silver (Ag) are co-deposited on the electron-injected layer at a deposition rate of 10%:90% to form a layer with a thickness of [missing information]. The cathode.

[0190] Finally, compound CP-1 is deposited on the cathode to form a thickness of [thickness value missing]. The cathode capping layer is used to complete the fabrication of the red organic electroluminescent device.

[0191] Examples 2-30

[0192] Except that, when preparing the light-emitting adjustment layer, the organic electroluminescent device was prepared using the same method as in Example 1, except that the compound in Table 6 was used instead of compound 73 in Example 1.

[0193] Comparative Examples 1-4

[0194] Except that when preparing the light-emitting adjustment layer, compounds A to D in Table 5 were used to replace compound 73 in Example 1, the organic electroluminescent device was prepared using the same method as in Example 1.

[0195] The material structures used in the above embodiments and comparative examples are shown in Table 5 below:

[0196] Table 5

[0197]

[0198]

[0199] The performance of the red organic electroluminescent devices prepared in Examples 1-30 and Comparative Examples 1-4 was tested, specifically at 15 mA / cm². 2 The IVL performance of the device was tested under the condition of 20 mA / cm. 2 Test T under the conditions 95 Device lifespan, test results are shown in Table 6 below.

[0200] Table 6

[0201]

[0202]

[0203] Referring to Table 6 above, it can be seen that when the compounds of this application are used in the luminescence adjustment layer of red organic electroluminescent devices, the device performance can be significantly improved. Specifically, compared with the organic electroluminescent devices of Comparative Examples 1 to 4, the organic electroluminescent devices of Examples 1 to 30 have an efficiency improvement of at least 14.6% and a lifetime improvement of at least 13.8%.

[0204] The preferred embodiments of the present invention have been described in detail above with reference to the accompanying drawings. However, the present invention is not limited to the specific details of the above embodiments. Within the scope of the technical concept of the present invention, various simple modifications can be made to the technical solutions of the present invention, and these simple modifications all fall within the protection scope of the present invention. Furthermore, it should be noted that the various specific technical features described in the above specific embodiments can be combined in any suitable manner without contradiction. To avoid unnecessary repetition, the present invention will not describe the various possible combinations separately. In addition, various different embodiments of the present invention can also be arbitrarily combined, as long as they do not violate the spirit of the present invention, and should also be considered as the content disclosed by the present invention.

Claims

1. An organic compound, characterized in that, The structure of the organic compound is shown in Formula 1: Formula 1 Where X is selected from O; L, L1, and L2 may be the same or different, and each is independently selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted phenanthylene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiopheneylene, or substituted or unsubstituted carbazolylene. The substituents in L, L1, and L2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, trimethylsilyl, or phenyl. Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl; The substituents in Ar1 and Ar2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, phenyl, naphthyl or trimethylsilyl; Each R m and R n They may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, trideuterated methyl or trifluoromethyl; m is R m The number of elements, m is selected from 0, 1, 2, 3, 4 or 5; n is R n The number of elements, n, is selected from 0, 1, 2, or 3.

2. The organic compound according to claim 1, characterized in that, L, L1, and L2 may be the same or different, and each is independently selected from the group consisting of a single bond or the following groups: 。 3. The organic compound according to claim 1, characterized in that, Ar1 and Ar2 may be the same or different, and each is independently selected from the following groups: 。 4. The organic compound according to claim 1, characterized in that, The organic compound is selected from the group consisting of the following compounds:

5. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes an anode, a cathode, and at least one functional layer disposed between the anode and the cathode, wherein the functional layer comprises an organic compound as described in any one of claims 1 to 4.

6. The organic electroluminescent device according to claim 5, characterized in that, The functional layer includes a light-emitting adjustment layer, which contains the organic compound.

7. An electronic device, characterized in that, Including the organic electroluminescent device as described in claim 5 or 6.

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