An organic compound and use thereof

Abstract

The application relates to the technical field of display, in particular to an organic compound and application thereof. The organic compound provided by the application can improve the carrier transport performance of the compound by modifying the parent nucleus based on the structure of the following formula (1) and limiting specific substituent groups on the parent nucleus, so that the organic electroluminescent device containing the organic compound has a lower driving voltage, a higher luminous efficiency and a longer service life.

Description

Technical Field

[0001] This invention relates to the field of display technology, and more specifically to an organic compound and its applications. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are highly integrated optical devices, with their core being a complex organic multilayer structure built between the cathode and anode. This system mainly includes multiple functional layers such as a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer (a precise combination of host material and dopants), a hole blocking layer, an electron transport layer, and an electron injection layer. Under appropriate voltage driving, OLEDs can effectively inject and recombine holes and electrons within the light-emitting layer, forming high-energy excited-state molecules. Subsequently, these excited-state molecules release energy in the form of light radiation during de-excitation, achieving efficient light emission.

[0003] However, existing organic electroluminescent materials have poor carrier transport performance, which leads to problems such as high driving voltage, low luminous efficiency and short lifetime in organic electroluminescent devices containing such materials, which seriously limits the application of organic electroluminescent devices. Summary of the Invention

[0004] The purpose of this invention is to overcome the poor carrier transport performance of existing organic electroluminescent materials, which results in high driving voltage, low luminous efficiency, and short lifetime of organic electroluminescent devices containing such materials, and to provide an organic compound and its application.

[0005] In the definition of substituent terms in this invention:

[0006] The term "organic electroluminescent material" in this disclosure refers to a material that can be used in an organic electroluminescent device and may contain at least one compound. If desired, the organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole assist material, a light-emitting assist material, an electron blocking material, a light-emitting material (containing a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0007] The term "multiple organic electroluminescent materials" in this disclosure refers to one or more organic electroluminescent materials comprising a combination of at least two compounds, said materials may be contained in any layer constituting an organic electroluminescent device. It can mean both materials contained before (e.g., before vapor deposition) and materials contained after (e.g., after vapor deposition) the organic electroluminescent device. For example, multiple organic electroluminescent materials may be a combination of at least two compounds, said materials may contain at least one of the following: a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The at least two compounds may be contained in the same layer or different layers, and may be mixed-evaporated or co-evaporated, or may be evaporated individually.

[0008] In this application, the descriptive terms “each…independently selected”, “…independently constitute”, and “…independently constitute” are interchangeable and should be interpreted broadly. They can mean that the specific options expressed by the same symbols in different groups do not affect each other, or that the specific options expressed by the same symbols in the same group do not affect each other.

[0009] In this application, the term "substituent" has its common meaning as known in the art, referring to a chemical moiety covalently attached to or, where appropriate, fused to a parent nucleus group.

[0010] 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 substituent, i.e., Rc, can be, for example, deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, or C1-C60 heteroaryl. Optionally, it can be, for example, deuterium, a halogen group, cyano, alkyl, haloalkyl, trialkylsilyl, deuterated alkyl, aryl, heteroaryl, etc. Of course, the number of substituents Rc can be one or more. When two substituents Rc are attached to the same atom, the two substituents Rc can exist independently or be connected to each other to form a ring with the atom; when two adjacent substituents Rc exist on a functional group, the adjacent substituents Rc can exist independently or fuse with the functional group to which they are attached to form a ring.

[0011] In this application, the term "alkyl" refers, whether as part of other terms or used alone, to a saturated hydrocarbon group, which may be straight-chain or branched. The term "C1-C60 alkyl" is derived from a monovalent substituent of a straight-chain or branched saturated hydrocarbon having 1 to 60 carbon atoms, preferably 1 to 40 carbon atoms, and more preferably 1 to 20 carbon atoms. Examples of such substituents include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.

[0012] In this application, the terms "aryl" and "arylene" include monocyclic, polycyclic, or fused-ring aryl groups. The rings of the polycyclic aryl group may be interrupted by short non-aromatic units, and may contain a spirostructure. Aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, fluorene, and spirodifluorene. Aarylene groups include, but are not limited to, phenylene, biphenylene, terphenylene, naphthyl, phenanthryl, anthracene, fluorene, and spirodifluorene.

[0013] In this application, the term "fused-ring aryl" refers to a polycyclic structure consisting of at least two fused aromatic rings, including but not limited to naphthyl, anthraceneyl, phenanthryl, trefyl, and triphenylene.

[0014] In this application, the term "heteroaryl" includes monocyclic, polycyclic, or fused-ring heteroaryl groups, wherein the rings may be interrupted by short non-aromatic units, and the heteroatoms include nitrogen, oxygen, and sulfur. Heteroaryl groups in this application include, but are not limited to, furanyl, phenylthio, pyrroleyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetraazinyl, triazolyl, tetraazolyl, furazolidyl, pyridinyl, pyrazinyl, and pyrimidineyl. Pyridyl, benzofuranyl, benzothiophene, isobenzofuranyl, dibenzofuranyl, dibenzothiophene, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisooxazolyl, benzooxazolyl, isoindolyl, indolyl, indazole, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxalolinyl, carbazole, phenoxazinyl, phenthiazinyl, phenanthidyl, benzo-m-dioxacyclopentenyl, dihydroacridyl And their derivatives, etc.; heteroaryl groups include, but are not limited to, pyrifos, pyrrolizyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridinyl, pyridazinyl, benzofuranyl, benzothiopheneyl, isobenzofuranyl, dibenzofuranyl Furanyl, dibenzothiophene, benzimidazolyl, benzithiazolyl, benzisisothiazolyl, benzisisooxazolyl, benzisoxazolyl, isoindolyl, indolyl, ininzolyl, benzisazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxolinyl, carbazolyl, phenoxazinyl, phenoxazinyl, phenanthridineyl, benzo[m]dioxacyclopentenyl, dihydroacridyl, and their derivatives, etc. As used herein, the term "substituted" means that a hydrogen atom in the compound is replaced by another substituent. This position is not limited to a specific position, as long as the hydrogen at that position can be replaced by a substituent. When two or more substituents are present, the two or more substituents can be the same or different.

[0015] In this application, the term "alkylaryl" refers to an aryl group that is substituted by at least one alkyl group, wherein the definitions of alkyl and aryl are the same as those described above, and the alkylaryl group includes, but is not limited to, methylphenyl, ethylphenyl, n-propylphenyl, isopropylphenyl, tert-butylphenyl, sec-butylphenyl, tert-butylphenyl, methylnaphthyl, ethylnaphthyl, etc.

[0016] In this application, the term "halogen" refers to an atom selected from fluorine, chlorine, bromine, and iodine.

[0017] In this application, unless otherwise stated, hydrogen atoms include protium, deuterium, and tritium.

[0018] In this application, the definition of a group specifies a range of carbon atoms, and the number of carbon atoms is any integer within the defined range, such as C6-C60 aryl. The number of carbon atoms representing an aryl group can be any integer within the range of 6-60, such as 6, 8, 10, 13, 15, 17, 20, 22, 25, 30, 35, 40, 45, 50, 55 or 60, etc.

[0019] Unless otherwise specified, the substituents in this application do not fuse with the group to which they belong.

[0020] In this application, if the group is not specified as substituted or unsubstituted, it means that it has not been substituted.

[0021] In a first aspect, the present invention provides an organic compound having the structure shown in formula (1):

[0022]

[0023] Ar is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C7-C60 alkylaryl, and substituted or unsubstituted C3-C60 heteroaryl.

[0024] R 1 R 2 Each is selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, and R 1 R 2 Each exists independently or is linked together to form substituted or unsubstituted C3-C60 aliphatic rings, substituted or unsubstituted C6-C60 aromatic rings, or substituted or unsubstituted C3-C60 heteroaromatic rings.

[0025] The substituents in the substituted C6-C60 aryl, substituted C7-C60 alkylaryl, substituted C3-C60 heteroaryl, substituted C1-C30 alkyl, substituted C1-C30 heteroalkyl, substituted C3-C60 aliphatic ring, substituted C6-C60 aromatic ring, and substituted C3-C60 heteroaryl ring are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaromatic amino.

[0026] Preferably, the substituents of the substituted C6-C60 aryl group, the substituted C3-C60 heteroaryl group, the substituted C1-C30 alkyl group, the substituted C1-C30 heteroalkyl group, the substituted C3-C60 aliphatic ring, the substituted C6-C60 aromatic ring, and the substituted C3-C60 heteroaryl ring are selected from deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexyl, cyclopentyl, phenyl, naphthyl, phenanthrene, phenylnaphthyl, naphthylphenyl, biphenyl, anthracene, fluorenyl, pyrene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzonaphthiofuranyl, benzonaphthiophene, carbazole, and benzocarbazole are selected from one or a combination of at least two of these groups.

[0027] Preferably, the organic compound is selected from the structures shown in Formula 1-1 to Formula 1-12, wherein Ar and R 1 R 2 The definition is the same as the definition above:

[0028]

[0029]

[0030] Preferably, Ar is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C7-C30 alkylaryl, and substituted or unsubstituted C3-C30 heteroaryl.

[0031] The substituents in the substituted C6-C30 aryl, substituted C7-C30 alkylaryl, and substituted C3-C30 heteroaryl are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaromatic amino.

[0032] Preferably, Ar is selected from substituted or unsubstituted C14-C30 aryl, substituted or unsubstituted C10-C30 alkylaryl, and substituted or unsubstituted C3-C30 heteroaryl.

[0033] The substituents in the substituted C14-C30 aryl, substituted C10-C30 alkylaryl, and substituted C3-C30 heteroaryl are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaromatic amino.

[0034] Preferably, Ar is selected from substituted or unsubstituted C14-C18 aryl, substituted or unsubstituted C10-C18 alkylaryl, and substituted or unsubstituted C3-C18 heteroaryl.

[0035] The substituents in the substituted C14-C18 aryl, substituted C10-C18 alkylaryl, and substituted C3-C18 heteroaryl are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaromatic amino.

[0036] Preferably, the substituents in the substituted C14-C18 aryl, substituted C10-C18 alkylaryl, and substituted C3-C18 heteroaryl groups are selected from deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexyl, cyclopentyl, phenyl, naphthyl, phenanthryl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracene, fluorenyl, pyrene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzonaphthiofuranyl, benzonaphthiophene, carbazole, and benzocarbazole.

[0037] Preferably, Ar is selected from substituted or unsubstituted C14-C18 fused-ring aryl, substituted or unsubstituted C10-C18 alkyl aryl, and substituted or unsubstituted C3-C18 heteroaryl.

[0038] The substituents in the substituted C14-C18 fused-ring aryl, substituted C10-C18 alkyl aryl, and substituted C3-C18 heteroaryl are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaromatic amino.

[0039] Preferably, the substituents in the substituted C14-C18 fused-ring aryl, substituted C10-C18 alkyl aryl, and substituted C3-C18 heteroaryl groups are selected from deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexyl, cyclopentyl, phenyl, naphthyl, phenanthrene, phenylnaphthyl, naphthylphenyl, biphenyl, anthracene, fluorenyl, pyrene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzonaphthiofuranyl, benzonaphthiophene, carbazole, and benzocarbazole are selected from one or a combination of at least two of these groups.

[0040] Preferably, Ar is selected from substituted or unsubstituted A groups, and the A group is selected from phenanthrene, tert-butylphenyl, trefyl, and triphenylene.

[0041] Wherein, the substituents in the substituted A group are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaryl.

[0042] Preferably, the substituents in the substituted A group are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexyl, cyclopentyl, phenyl, naphthyl, phenanthryl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracene, fluorenyl, pyrene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzonaphthiofuranyl, benzonaphthiophene, carbazole, and benzocarbazole.

[0043] Preferred, R 1 R 2 Each of the following is selected from substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C1-C15 heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and R1 and R2 exist independently or are bonded to each other to form a substituted or unsubstituted C3-C30 aliphatic ring, a substituted or unsubstituted C6-C30 aromatic ring, or a substituted or unsubstituted C3-C30 heteroaromatic ring;

[0044] The substituents in the substituted C1-C15 alkyl, substituted C1-C15 heteroalkyl, substituted C6-C30 aryl, substituted C3-C30 heteroaryl, substituted C3-C30 aliphatic ring, substituted C6-C30 aromatic ring, and substituted C3-C30 heteroaryl ring are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaromatic amino.

[0045] Preferred, R 1 R 2 Each of the following is selected from substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C1-C6 heteroalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl, and R1 and R2 exist independently or are bonded to each other to form a substituted or unsubstituted C3-C18 aliphatic ring, a substituted or unsubstituted C6-C18 aromatic ring, or a substituted or unsubstituted C3-C18 heteroaromatic ring;

[0046] The substituents in the substituted C1-C6 alkyl, substituted C1-C6 heteroalkyl, substituted C6-C18 aryl, substituted C3-C18 heteroaryl, substituted C3-C18 aliphatic ring, substituted C6-C18 aromatic ring, and substituted C3-C18 heteroaryl ring are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaryl.

[0047] Preferably, the substituents in the substituted C1-C6 alkyl, substituted C1-C6 heteroalkyl, substituted C6-C18 aryl, substituted C3-C18 heteroaryl, substituted C3-C18 aliphatic ring, substituted C6-C18 aromatic ring, and substituted C3-C18 heteroaryl ring are selected from deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexyl, cyclopentyl, phenyl, naphthyl, phenanthrene, phenylnaphthyl, naphthylphenyl, biphenyl, anthracene, fluorenyl, pyrene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzonaphthiofuranyl, benzonaphthiophene, carbazole, and benzocarbazole are selected from one or a combination of at least two of these.

[0048] Preferred, R 1 R 2 Each group is independently selected from substituted or unsubstituted B groups, wherein the B group is selected from methyl, ethyl, propyl, tert-butyl, sec-butyl, tert-butyl, methoxy, methylthio, ethoxy, ethylthio, phenyl, naphthyl, phenanthryl, tretinoin, and triphenylene, and R 1 R 2 They exist independently or are linked together to form substituted or unsubstituted pentyl rings, substituted or unsubstituted hexyl rings, and substituted or unsubstituted fluorene rings;

[0049] Wherein, the substituents in the substituted B group, substituted pentane ring, substituted hexane ring, and substituted fluorene ring are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaryl.

[0050] Preferably, the substituents of the substituted B group, substituted pentyl ring, substituted hexyl ring, and substituted fluorene ring are selected from deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexyl, cyclopentyl, phenyl, naphthyl, phenanthryl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracene, fluorene, pyrene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzonaphthiofuranyl, benzonaphthiophene, carbazole, and benzocarbazole.

[0051] Preferably, the organic compound is selected from any of the following structures:

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070] Optionally, the deuteration rate of the compounds described above is 0%-100%.

[0071] Secondly, the present invention also provides a method for preparing the above-mentioned organic compound, as follows:

[0072]

[0073] In the above reaction, Y is Bpin or B(OH)2, and Ar and R are... 1 R 2 The definition is the same as the definition described above;

[0074] The intermediate sub-2-n can be prepared by the following method:

[0075]

[0076] The raw materials ax, bx, cx, and dx can be purchased directly or synthesized using conventional reaction pathways and conditions by referring to existing literature reports.

[0077] Thirdly, the present invention also provides an organic electroluminescent material comprising the organic compounds described above.

[0078] Fourthly, the present invention also provides an organic electroluminescent device, the organic electroluminescent device comprising a cathode, an anode, and an organic layer located between the cathode and the anode, the organic layer comprising the organic compound or the organic electroluminescent material described above.

[0079] Preferably, the organic layer located between the cathode and the anode includes any one or a combination of at least two of the following: a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0080] Optionally, the organic layer includes a hole injection layer to enhance the ability to inject holes into the hole transport layer. The hole injection layer may be selected from benzidine derivatives, arylamine compounds, phthalocyanine derivatives, the organic compounds described in formula (1), or other materials; this application does not impose any special limitations on this. The material of the hole injection layer includes, but is not limited to, the organic compounds described in formula (1) or the following compounds:

[0081]

[0082]

[0083] Optionally, the organic layer includes a hole transport layer, which may include one or more hole transport materials. The hole transport materials may be selected from carbazole polymers, carbazole-linked triarylamine compounds, the organic compounds described in formula (1), or other types of compounds. This application does not impose any special limitations on this. The material of the hole injection layer includes, but is not limited to, the organic compounds described in formula (1) or the following compounds:

[0084]

[0085]

[0086] Preferably, the organic layer includes a light-emitting auxiliary layer, which can be a single layer or a multilayer structure, and the light-emitting auxiliary layer contains the organic compound of formula (1).

[0087] Preferably, the organic layer includes a light-emitting layer, which includes a host material and a guest material. The host material includes multiple host materials or a single host material. The composition of the multiple host materials or the single host material includes, but is not limited to, aromatic amine compounds and their derivatives, triazine compounds and their derivatives, carbazole compounds and their derivatives. This application does not impose any special restrictions on this. The host material is also referred to as the matrix material.

[0088] The guest material can be a compound having a condensed aryl ring or its derivative, a compound having a heteroaryl ring or its derivative, an aromatic amine derivative, or other materials, and this application does not impose any special limitations on this; the guest material is also referred to as a dopant or dopant. The guest material includes, but is not limited to, the following structures:

[0089]

[0090] Optionally, the organic layer includes a hole-blocking layer, which can be a single-layer or multi-layer structure.

[0091] Optionally, the organic layer includes an electron transport layer, which can be a single-layer structure or a multi-layer structure. It may include one or more electron transport materials, selected from, but not limited to, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. This application does not impose any special limitations on this. The materials of the electron transport layer include, but are not limited to, the following structures:

[0092]

[0093]

[0094] Optionally, an electron injection layer is provided between the cathode and the electron transport layer to enhance the ability to inject electrons into the electron transport layer. The electron injection layer may include inorganic materials such as alkali metal sulfides and alkali metal halides, or it may include complexes of alkali metals and organic materials.

[0095] Fifthly, the present invention also provides an electronic device, characterized in that the electronic device comprises an organic electroluminescent device as described above, an organic electroluminescent material as described above, or an organic compound as shown in formula (1).

[0096] The above can be combined freely.

[0097] The beneficial effects of this invention are:

[0098] The organic compound provided by the present invention can improve the carrier transport performance of the compound by modifying the core with specific substituents based on the core of the structure of formula (1), and ultimately enable the organic electroluminescent device containing the organic compound to have a lower driving voltage, higher luminous efficiency and longer lifetime. Attached Figure Description

[0099] To more clearly illustrate the specific embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the specific embodiments or the prior art will be briefly introduced below. Obviously, the drawings described below are some embodiments of the present invention. For those skilled in the art, other drawings can be obtained from these drawings without creative effort.

[0100] Figure 1 This is a structural diagram of the organic electroluminescent device in the device embodiment of the present invention;

[0101] 1 – Substrate; 2 – Anode; 3 – Hole injection layer; 4 – Hole transport layer; 5 – Light emission auxiliary layer; 6 – Light emission layer; 7 – Electron transport layer; 8 – Electron injection layer; 9 – Cathode. Detailed Implementation

[0102] The following embodiments are provided to better understand the present invention and are not limited to the preferred embodiments described. They do not constitute a limitation on the content and scope of protection of the present invention. Any product that is the same as or similar to the present invention, derived by any person under the guidance of the present invention or by combining the features of the present invention with other prior art, is within the scope of protection of the present invention.

[0103] For experiments not specifically described in the examples, the procedures or conditions should be followed according to the conventional experimental procedures described in the literature in this field. Reagents or instruments whose manufacturers are not specified are all commercially available conventional reagent products.

[0104] Those skilled in the art will recognize that the chemical reactions described herein can be suitably used to prepare many of the heterocyclic compounds of this application, and other methods for preparing the compounds of this application are considered to be within the scope of this application. For example, the synthesis of those non-illustrative compounds according to this application can be successfully accomplished by those skilled in the art through modification methods, such as appropriately protecting interfering groups, utilizing other known reagents besides those described herein, or making some conventional modifications to the reaction conditions. Compounds for which synthetic methods are not mentioned in this application are commercially available starting materials.

[0105] The specific structures of the raw materials ax, bx, cx, and dx used in this embodiment of the invention are as follows:

[0106] In this embodiment of the invention, the raw material ax comprises the following structure:

[0107]

[0108] In this embodiment of the invention, the raw material bx comprises the following structure:

[0109]

[0110] In this embodiment of the invention, the raw material cx comprises the following structure:

[0111]

[0112]

[0113] In this embodiment of the invention, the raw material dx comprises the following structure:

[0114]

[0115] Synthesis of intermediate sub-2-n:

[0116] Synthesis of intermediate sub-2-117:

[0117]

[0118] Synthesis of sub-2-117: 12 g of compound c-1 (35.92 mmol), 5.36 g of compound d-1 (35.92 mmol), 0.33 g of Pd2(dba)3 (0.36 mmol), 0.34 g of X-phos (0.72 mmol), and 6.90 g of t-BuONa (71.85 mmol) were added to a 250 mL three-necked flask. 120 mL of toluene was added to the flask, and the mixture was purged with nitrogen and stirred at 110 °C for 2 h. After the reaction was complete, compound sub-2-117 (76% yield) was obtained by column chromatography.

[0119] Referring to the synthesis method above, by replacing intermediates cx and dx, a series of intermediates sub-2-117 can be obtained. The intermediate structures provided in the embodiments of the present invention are shown in Table 1:

[0120] Table 1

[0121]

[0122]

[0123] Synthesis Example 1

[0124] This embodiment provides the synthesis of compound N-5, and its synthetic route is shown below:

[0125]

[0126] Synthesis of intermediate sub-1-5: 6.77 g of compound a-1 (28.23 mmol), 10 g of compound b-1 (28.23 mmol), 0.33 g of Pd(Pph3)4 (0.28 mmol), and 7.79 g of K2CO3 (56.47 mmol) were added to a 500 mL three-necked flask. 90 mL of 1,4-dioxane and 30 mL of water were added, and the mixture was purged with nitrogen. The mixture was stirred at 85 °C for 2 hours. After the reaction was complete, intermediate sub-1-5 (7.73 g, 70% yield) was obtained by column chromatography.

[0127] Synthesis of compound N-5: 7.73 g of intermediate sub-1-5 (19.92 mmol), 6.80 g of intermediate sub-2-5 (19.92 mmol), 0.18 g of Pd2(dba)3 (0.20 mmol), 0.16 g of S-phos (0.40 mmol), and 3.83 g of t-BuONa (39.84 mmol) obtained above were added to a 250 mL three-necked flask. 80 mL of xylene was added to the flask, and the mixture was purged with nitrogen. The mixture was stirred at 140 °C for 2 hours. After the reaction was complete, compound N-5 (9.32 g, yield 67%) was obtained by column chromatography.

[0128] Elemental analysis: C 53 H 43 N, theoretical value: C, 91.74; H, 6.25; N, 2.02; measured value: C, 91.77; H, 6.27; N, 2.01; HRMS(ESI)m / z[M+H]+: theoretical value: 693.34; measured value: 694.21.

[0129] Synthesis Example 2

[0130] This embodiment provides the synthesis of compound N-55, and its synthetic route is shown below:

[0131]

[0132] Synthesis of intermediate sub-1-55: The synthesis method of intermediate sub-1-55 is the same as that of sub-1-5, except that raw material a-1 is replaced with raw material a-2 and raw material b-1 is replaced with raw material b-2, thus obtaining intermediate sub-1-55 (yield 60%).

[0133] Synthesis of compound N-55: The synthesis method of compound N-55 is the same as that of N-5, except that intermediate sub-1-5 is replaced with intermediate sub-1-55, thus obtaining compound N-55 (yield 73%).

[0134] Elemental analysis: C 49 H 41 N, theoretical value: C, 91.41; H, 6.42; N, 2.18; measured value: C, 91.47; H, 6.43; N, 2.15; HRMS(ESI)m / z[M+H]+: theoretical value: 643.32; measured value: 644.29.

[0135] Synthesis Example 3

[0136] This embodiment provides the synthesis of compound N-88, and its synthetic route is shown below:

[0137]

[0138] Synthesis of intermediate sub-1-88: The synthesis method of intermediate sub-1-88 is the same as that of sub-1-5, except that raw material a-1 is replaced with raw material a-2, thus obtaining intermediate sub-1-88 (yield 65%).

[0139] Synthesis of compound N-88: The synthesis method of compound N-88 is the same as that of N-5, except that intermediate sub-1-5 is replaced with intermediate sub-1-88 and intermediate sub-2-5 is replaced with intermediate sub-2-88, thus obtaining compound N-88 (yield 70%).

[0140] Elemental analysis: C 53 H 43 N, theoretical value: C, 91.74; H, 6.25; N, 2.02; measured value: C, 91.75; H, 6.26; N, 2.01; HRMS(ESI)m / z[M+H]+: theoretical value: 693.34; measured value: 694.29.

[0141] Synthesis Example 4

[0142] This embodiment provides the synthesis of compound N-95, and its synthetic route is shown below:

[0143]

[0144] Synthesis of intermediate sub-1-95: The synthesis method of intermediate sub-1-95 is the same as that of sub-1-5, except that raw material a-1 is replaced with raw material a-3 and raw material b-1 is replaced with raw material b-3, thus obtaining intermediate sub-1-95 (yield 63%).

[0145] Synthesis of compound N-95: The synthesis method of compound N-95 is the same as that of N-5, except that intermediate sub-1-5 is replaced with intermediate sub-1-95 and intermediate sub-2-5 is replaced with intermediate sub-2-95, thus obtaining compound N-95 (yield 64%).

[0146] Elemental analysis: C 53 H 43 N, theoretical value: C, 91.74; H, 6.25; N, 2.02; measured value: C, 91.80; H, 6.25; N, 1.99; HRMS(ESI)m / z[M+H]+: theoretical value: 693.34; measured value: 694.28.

[0147] Synthesis Example 5

[0148] This embodiment provides the synthesis of compound N-117, and its synthetic route is shown below:

[0149]

[0150] Synthesis of intermediate sub-1-117: The synthesis method of intermediate sub-1-117 is the same as that of sub-1-5, except that raw material a-1 is replaced with raw material a-4 and raw material b-1 is replaced with raw material b-4, thus obtaining intermediate sub-1-117 (yield 67%).

[0151] Synthesis of compound N-117: The synthesis method of compound N-117 is the same as that of N-5, except that intermediate sub-1-5 is replaced with intermediate sub-1-117 and intermediate sub-2-5 is replaced with intermediate sub-2-117, thus obtaining compound N-117 (yield 80%).

[0152] Elemental analysis: C 54 H 43 N, theoretical value: C, 91.88; H, 6.14; N, 1.98; measured value: C, 91.92; H, 6.13; N, 2.01; HRMS(ESI)m / z[M+H]+: theoretical value: 705.34; measured value: 706.18.

[0153] Synthesis Example 6

[0154] This embodiment provides the synthesis of compound N-149, and its synthetic route is shown below:

[0155]

[0156] Synthesis of intermediate sub-1-149: The synthesis method of intermediate sub-1-149 is the same as that of sub-1-5, except that raw material a-1 is replaced with raw material a-5 and raw material b-1 is replaced with raw material b-5, thus obtaining intermediate sub-1-149 (yield 64%).

[0157] Synthesis of compound N-149: The synthesis method of compound N-149 is the same as that of N-5, except that intermediate sub-1-5 is replaced with intermediate sub-1-149 and intermediate sub-2-5 is replaced with intermediate sub-2-149, thus obtaining compound N-149 (yield 71%).

[0158] Elemental analysis: C 63 H 47 N, theoretical value: C, 92.50; H, 5.79; N, 1.71; measured value: C, 92.55; H, 5.80; N, 1.68; HRMS(ESI)m / z[M+H]+: theoretical value: 817.37; measured value: 818.29.

[0159] Synthesis Example 7

[0160] This embodiment provides the synthesis of compound N-194, and its synthetic route is shown below:

[0161]

[0162] Synthesis of intermediate sub-1-194: The synthesis method of intermediate sub-1-194 is the same as that of sub-1-5, except that raw material a-1 is replaced with raw material a-2 and raw material b-1 is replaced with raw material b-5, thus obtaining intermediate sub-1-194 (yield 69%).

[0163] Synthesis of compound N-194: The synthesis method of compound N-194 is the same as that of N-5, except that intermediate sub-1-5 is replaced with intermediate sub-1-194 and intermediate sub-2-5 is replaced with intermediate sub-2-88, thus obtaining compound N-194 (yield 74%).

[0164] Elemental analysis: C 53 H 43N, theoretical value: C, 91.74; H, 6.25; N, 2.02; measured value: C, 91.73; H, 6.27; N, 2.03; HRMS(ESI)m / z[M+H]+: theoretical value: 693.34; measured value: 694.43.

[0165] Synthesis Example 8

[0166] This embodiment provides the synthesis of compound N-197, and its synthetic route is shown below:

[0167]

[0168] Synthesis of intermediate sub-1-197: The synthesis method of intermediate sub-1-197 is the same as that of sub-1-5, except that raw material b-1 is replaced with raw material b-6, thus obtaining intermediate sub-1-197 (yield 68%).

[0169] Synthesis of compound N-197: The synthesis method of compound N-197 is the same as that of N-5, except that intermediate sub-1-5 is replaced with intermediate sub-1-197 and intermediate sub-2-5 is replaced with intermediate sub-2-197, thus obtaining compound N-197 (yield 72%).

[0170] Elemental analysis: C 55 H 47 N, theoretical value: C, 91.50; H, 6.56; N, 1.94; measured value: C, 91.52; H, 6.55; N, 1.94; HRMS(ESI)m / z[M+H]+: theoretical value: 721.37; measured value: 722.33.

[0171] Synthesis Example 9

[0172] This embodiment provides the synthesis of compound N-208, and its synthetic route is shown below:

[0173]

[0174] Synthesis of intermediate sub-1-208: The synthesis method of intermediate sub-1-208 is the same as that of sub-1-5, except that raw material a-1 is replaced with raw material a-6 and raw material b-1 is replaced with raw material b-6, thus obtaining intermediate sub-1-208 (yield 69%).

[0175] Synthesis of compound N-208: The synthesis method of compound N-208 is the same as that of N-5, except that intermediate sub-1-5 is replaced with intermediate sub-1-208 and intermediate sub-2-5 is replaced with intermediate sub-2-208, thus obtaining compound N-208 (yield 81%).

[0176] Elemental analysis: C 48 H 49 N, theoretical value: C, 90.09; H, 7.72; N, 2.19; measured value: C, 90.12; H, 7.71; N, 2.20; HRMS(ESI) m / z [M+H]+: theoretical value: 639.39; measured value: 640.21

[0177] Synthesis Example 10

[0178] This embodiment provides the synthesis of compound N-216, and its synthetic route is shown below:

[0179]

[0180] Synthesis of intermediate sub-1-216: The synthesis method of intermediate sub-1-216 is the same as that of sub-1-5, except that raw material b-1 is replaced with raw material b-7, thus obtaining intermediate sub-1-216 (yield 69%).

[0181] Synthesis of compound N-216: The synthesis method of compound N-216 is the same as that of N-5, except that intermediate sub-1-5 is replaced with intermediate sub-1-216 and intermediate sub-2-5 is replaced with intermediate sub-2-216, thus obtaining compound N-216 (yield 81%).

[0182] Elemental analysis: C 55 H 45 N, theoretical value: C, 91.75; H, 6.30; N, 1.95; measured value: C, 91.77; H, 6.32; N, 1.90; HRMS(ESI)m / z[M+H]+: theoretical value: 719.36; measured value: 720.28.

[0183] Synthesis Example 11

[0184] This embodiment provides the synthesis of compound N-243, and its synthetic route is shown below:

[0185]

[0186] Synthesis of compound N-243: The synthesis method of compound N-243 is the same as that of N-5, except that intermediate sub-1-5 is replaced with intermediate sub-1-55 and intermediate sub-2-5 is replaced with intermediate sub-2-88, thus obtaining compound N-243 (yield 81%).

[0187] Elemental analysis: C 49 H 41 N, theoretical value: C, 91.41; H, 6.42; N, 2.18; measured value: C, 91.43; H, 6.43; N, 2.16; HRMS(ESI)m / z[M+H]+: theoretical value: 643.32; measured value: 644.58.

[0188] Synthesis Example 12

[0189] This embodiment provides the synthesis of compound N-285, and its synthetic route is shown below:

[0190]

[0191] Synthesis of intermediate sub-1-285: The synthesis method of intermediate sub-1-285 is the same as that of sub-1-5, except that raw material a-1 is replaced with raw material a-2 and raw material b-1 is replaced with raw material b-8, thus obtaining intermediate sub-1-285 (yield 67%).

[0192] Synthesis of compound N-285: The synthesis method of compound N-285 is the same as that of N-5, except that intermediate sub-1-5 is replaced with intermediate sub-1-285 and intermediate sub-2-5 is replaced with intermediate sub-2-88, thus obtaining compound N-285 (yield 69%).

[0193] Elemental analysis: C 45 H 45 N, theoretical value: C, 90.10; H, 7.56; N, 2.34; measured value: C, 90.13; H, 7.55; N, 2.33; HRMS(ESI)m / z[M+H]+: theoretical value: 599.36; measured value: 600.41.

[0194] Device Examples

[0195] This invention also provides OLED devices composed of different organic electroluminescent materials, with specific structural distributions as follows: Figure 1As shown, the OLED device has the following layer structure: substrate (glass substrate) 1 / anode 2 (indium tin oxide (ITO) coating on the glass substrate) / hole injection layer 3 (HIL) / hole transport layer 4 (HTL) / light-emitting auxiliary layer 5 (Prime) / light-emitting layer 6 (EML) / electron transport layer 7 (ETL) / electron injection layer (EIL) 8 / cathode 9.

[0196] The compound structures of some of the device fabrication examples are shown below:

[0197]

[0198] The fabrication methods of devices in Examples 1-12 and Comparative Example 1 include the following steps:

[0199] (1) Substrate cleaning:

[0200] The glass substrate coated with transparent ITO was ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: ethylene glycol solvent ≤10wt%, triethanolamine ≤1wt%), rinsed in deionized water, ultrasonically degreased in an acetone:ethanol mixed solvent (volume ratio 1:1), baked in a clean environment until all moisture was removed, and then cleaned with ultraviolet light and ozone.

[0201] (2) Evaporation of organic light-emitting functional layer:

[0202] The glass substrate with the anode layer was placed in a vacuum chamber and evacuated to a vacuum level of 1×10⁻⁶. -6 Up to 2×10 -4 Pa, a mixture of HI-10 and HT-13 is vacuum-deposited on the above-mentioned anodic layer as a hole injection layer, wherein the mass ratio of HI-10 to HT-13 is 3:97 and the deposition thickness is 10 nm;

[0203] A hole transport layer (material HT-13) is deposited on the hole injection layer, with a film thickness of 80 nm.

[0204] A light-emitting auxiliary layer (Prime) is deposited on the hole transport layer. The material is as described in Table 2, and the film thickness is 5 nm.

[0205] The light-emitting layer is deposited on the light-emitting auxiliary layer. The specific preparation method is as follows: the light-emitting host material (CBP) and the guest material RD-14 are vacuum deposited by co-evaporation (as shown in Table 2), and the total film thickness is 35nm.

[0206] An electron transport layer is deposited on the light-emitting layer. The specific preparation method is as follows: ET-9 and LiQ are vacuum deposited by co-evaporation, wherein the mass ratio of ET-9 and LiQ is 50:50 and the total film thickness is 30nm.

[0207] An electron injection layer (LiQ material) was vacuum-deposited on the electron transport layer, with a total film thickness of 1 nm.

[0208] Al was deposited as the cathode on the electron injection layer, and the total film thickness was 90 nm.

[0209] Table 2 below shows the material and thickness parameters of each layer in Device Examples 1-12 and Device Comparative Example 1:

[0210] Table 2

[0211]

[0212] The organic electroluminescent devices obtained in Device Examples 1-12 and Device Comparative Example 1 were tested.

[0213] Instruments: The current, voltage, brightness, emission spectrum and other characteristics of the device were tested simultaneously using a PR650 spectral scanning luminance meter and a Keithley K2400 digital source meter system;

[0214] Test conditions: Photoelectric property test conditions: current density 10 mA / cm² 2 .

[0215] Lifetime test: current density 50mA / cm 2 The recording time (in hours) is recorded when the device brightness drops to 95% of its original brightness.

[0216] The device performance test results are shown in Table 3. To better demonstrate the performance advantages of this invention, the current efficiency test data of Comparative Example 1 in Table 3 is set to 100, and the current efficiency data of the device embodiments are all relative values ​​to it. Similarly, the lifetime test data of Comparative Example 1 in Table 3 is set to 100, and the lifetime test data of the device embodiments are all relative values ​​to it.

[0217] Table 3

[0218] project Drive voltage (V) Current efficiency Lifespan T95 Device Example 1 4.26 114.8 109 Device Example 2 4.18 116.1 115 Device Example 3 4.26 114.7 114 Device Example 4 4.25 114.9 110 Device Example 5 4.31 114.8 108 Device Example 6 4.33 114.5 109 Device Example 7 4.24 116.7 111 Device Example 8 4.27 115.1 109 Device Example 9 4.42 110.7 107 Device Example 10 4.33 114.9 109 Device Example 11 4.32 116.3 113 Device Example 12 4.36 111.0 108 Device Comparison Example 1 4.81 100 100

[0219] Obviously, the above embodiments are merely illustrative examples for clear explanation and are not intended to limit the implementation. Those skilled in the art will recognize that other variations or modifications can be made based on the above description. It is neither necessary nor possible to exhaustively list all possible implementations here. However, obvious variations or modifications derived therefrom are still within the scope of protection of this invention.

Claims

1. An organic compound, characterized in that, The organic compound has the structure shown in formula (1): Ar is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C7-C60 alkylaryl, and substituted or unsubstituted C3-C60 heteroaryl. R 1 R 2 Each is selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, and R 1 R 2 Each exists independently or is linked together to form substituted or unsubstituted C3-C60 aliphatic rings, substituted or unsubstituted C6-C60 aromatic rings, or substituted or unsubstituted C3-C60 heteroaromatic rings. The substituents in the substituted C6-C60 aryl, substituted C7-C60 alkylaryl, substituted C3-C60 heteroaryl, substituted C1-C30 alkyl, substituted C1-C30 heteroalkyl, substituted C3-C60 aliphatic ring, substituted C6-C60 aromatic ring, and substituted C3-C60 heteroaryl ring are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaromatic amino.

2. The organic compound according to claim 1, characterized in that, The organic compound is selected from the structures shown in Formulas 1-1 to 1-12, wherein Ar and R 1 R 2 The definition is the same as that in claim 1:

3. The organic compound according to claim 1 or 2, characterized in that, Ar is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C7-C30 alkylaryl, and substituted or unsubstituted C3-C30 heteroaryl; The substituents in the substituted C6-C30 aryl, substituted C7-C30 alkylaryl, and substituted C3-C30 heteroaryl are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaromatic amino. Preferably, Ar is selected from substituted or unsubstituted C14-C30 aryl, substituted or unsubstituted C10-C30 alkylaryl, and substituted or unsubstituted C3-C30 heteroaryl. The substituents in the substituted C14-C30 aryl, substituted C10-C30 alkylaryl, and substituted C3-C30 heteroaryl are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaromatic amino. Preferably, Ar is selected from substituted or unsubstituted A groups, and the A group is selected from phenanthrene, tert-butylphenyl, trefyl, and triphenylene. Wherein, the substituents in the substituted A group are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaryl. Preferably, the substituents in the substituted A group are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexyl, cyclopentyl, phenyl, naphthyl, phenanthryl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracene, fluorenyl, pyrene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzonaphthiofuranyl, benzonaphthiophene, carbazole, and benzocarbazole. Preferred, R 1 R 2 Each of the following is selected from substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C1-C15 heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and R1 and R2 exist independently or are bonded to each other to form a substituted or unsubstituted C3-C30 aliphatic ring, a substituted or unsubstituted C6-C30 aromatic ring, or a substituted or unsubstituted C3-C30 heteroaromatic ring; The substituents in the substituted C1-C15 alkyl, substituted C1-C15 heteroalkyl, substituted C6-C30 aryl, substituted C3-C30 heteroaryl, substituted C3-C30 aliphatic ring, substituted C6-C30 aromatic ring, and substituted C3-C30 heteroaryl ring are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaromatic amino. Preferred, R 1 R 2 Each group is independently selected from substituted or unsubstituted B groups, wherein the B group is selected from methyl, ethyl, propyl, tert-butyl, sec-butyl, tert-butyl, methoxy, methylthio, ethoxy, ethylthio, phenyl, naphthyl, phenanthryl, tretinoin, and triphenylene, and R 1 R 2 They exist independently or are linked together to form substituted or unsubstituted pentyl rings, substituted or unsubstituted hexyl rings, and substituted or unsubstituted fluorene rings; Wherein, the substituents in the substituted B group, substituted pentane ring, substituted hexane ring, and substituted fluorene ring are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaryl. Preferably, the substituents of the substituted B group, substituted pentyl ring, substituted hexyl ring, and substituted fluorene ring are selected from deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexyl, cyclopentyl, phenyl, naphthyl, phenanthryl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracene, fluorene, pyrene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzonaphthiofuranyl, benzonaphthiophene, carbazole, and benzocarbazole.

4. The organic compound according to any one of claims 1-3, characterized in that, The organic compound is selected from any of the following structures:

5. An organic electroluminescent material, characterized in that, The organic electroluminescent material comprises an organic compound as described in any one of claims 1-4.

6. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes an anode, a cathode, and an organic layer located between the anode and the cathode, wherein the organic layer includes an organic compound as described in any one of claims 1-4 or an organic electroluminescent material as described in claim 5.

7. The organic electroluminescent device according to claim 6, characterized in that, The organic layer includes any one or a combination of at least two of the following: a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

8. The organic electroluminescent device according to claim 6 or 7, characterized in that, The organic layer includes a light-emitting layer, which comprises an organic compound as described in any one of claims 1-4.

9. The organic electroluminescent device according to any one of claims 6-8, characterized in that, The organic layer includes one or a combination of at least two of the following: a light-emitting auxiliary layer, a hole transport layer, and a hole injection layer. At least one of the light-emitting auxiliary layer, the hole transport layer, and the hole injection layer includes an organic compound as described in any one of claims 1-4 or an organic electroluminescent material as described in claim 5.

10. An electronic device, characterized in that, The electronic device includes an organic electroluminescent device as described in any one of claims 6-9 or an organic electroluminescent material as described in claim 5, or an organic compound as described in any one of claims 1-4.

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