Organic compound and application thereof

Abstract

The invention relates to the technical field of display, in particular to an organic compound and application thereof. According to the organic compound provided by the invention, a substituent group Ar2 is introduced to a ring A of a formula (1), so that the substituent group Ar2 of the compound shown in the formula (1) and a carbazole fragment can generate a better conjugation effect, the electron donating capability of a donor fragment of the compound is remarkably improved, and further the intramolecular dipole moment of the compound can be effectively enhanced; therefore, the organic compound plays a role in accelerating the transmission and recombination of excitons in molecules, so that the organic electroluminescent device containing the organic compound has lower driving voltage, higher luminous efficiency and longer service life.

Description

Technical Field

[0001] The present invention relates to the field of display technology, and in particular to an organic compound and application thereof. Background Art

[0002] An organic electroluminescent device (OLED) is a device that changes electrical energy into light by applying electricity to an organic electroluminescent material, and generally has a structure comprising an anode, a cathode, and an organic layer between the anode and the cathode. The organic layer of the organic EL device can be composed of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (which comprises a host material and a doping material), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc., and the materials used for the organic layer are classified into hole injection materials, hole transport materials, electron blocking materials, light-emitting materials, electron buffer materials, hole blocking materials, electron transport materials, electron injection materials, etc. by their functions. In the organic EL device, due to the application of voltage, holes are injected from the anode into the light-emitting layer, electrons are injected from the cathode into the light-emitting layer, and high-energy excitons are formed by the recombination of holes and electrons. Through this energy, the organic light-emitting compound reaches an excited state, and luminescence is generated by emitting light due to the energy generated by the excited state of the organic light-emitting compound returning to the ground state.

[0003] The most important factor that determines the luminous efficiency in an organic EL device is the luminescent material. The luminescent material must have high quantum efficiency, high electron and hole mobility, and the luminescent material layer formed must be uniform and stable. The luminescent material is divided into blue luminescent material, green luminescent material, and red luminescent material according to the color of the luminescent light, and additionally yellow luminescent material or orange luminescent material. In addition, the luminescent material can also be divided into a host material and a doping material according to its function.

[0004] However, the existing organic compounds have poor application performance, which in turn causes the organic electroluminescent devices containing the organic electroluminescent materials to have high driving voltage, low luminous efficiency and short life, which seriously limits the application of organic electroluminescent devices. Summary of the invention

[0005] The purpose of the present invention is to overcome the problem of poor application performance of existing organic compounds, which causes the organic electroluminescent device containing the organic compound to have a higher driving voltage, lower luminous efficiency and shorter life, and further provide an organic compound and its application.

[0006] Definitions of substituent terms in this invention:

[0007] The term "organic electroluminescent material" in the present disclosure means a material that can be used in an organic electroluminescent device and can contain at least one compound. If necessary, the organic electroluminescent material can be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, a luminescence auxiliary material, an electron blocking material, a luminescent 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.

[0008] The term "multiple organic electroluminescent materials" in the present disclosure means one or more organic electroluminescent materials comprising a combination of at least two compounds, which may be included in any layer constituting an organic electroluminescent device. It may mean both a material contained in an organic electroluminescent device before (e.g., before vapor deposition) and a material contained in an organic electroluminescent device after (e.g., after vapor deposition). For example, a plurality of organic electroluminescent materials may be a combination of at least two compounds, which may be included in at least one of the following: a hole injection layer, a hole transport layer, a hole auxiliary layer, a luminescent auxiliary layer, a luminescent auxiliary layer, a luminescent layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. At least two compounds may be included in the same layer or in different layers, and may be mixed-evaporated or co-evaporated, or may be evaporated individually.

[0009] In the present application, the description methods used "each... is independently selected from" and "... are independently" and "... are independently" can be interchanged, and should be understood in a broad sense. It can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or it can mean that in the same group, the specific options expressed by the same symbols do not affect each other.

[0010] In this application, the term "substituent" has its ordinary meaning as known in the art and refers to a chemical moiety that is covalently attached to or, where appropriate, fused to a parent core group.

[0011] In the present application, the term "substituted or unsubstituted" means that the functional group recorded after the term may or may not have a substituent (hereinafter, for ease of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl or non-substituted aryl having a substituent Rc. Wherein the above-mentioned substituent, i.e., Rc, can be, for example, deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C1-C60 heteroaryl, and optionally, for example, deuterium, 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 connected 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 be fused to form a ring with the functional group to which they are connected.

[0012] In the present application, the term "alkyl" refers to a saturated hydrocarbon group, whether used as part of other terms or alone, which can be straight or branched. The term "C1-C60 alkyl" is derived from a monovalent substituent of a straight or branched saturated hydrocarbon having 1 to 60 carbon atoms, preferably 1 to 40 carbon atoms, and more preferably 1 to 20 carbon atoms, of course, examples thereof include but are not limited to methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl and hexyl.

[0013] In the present application, the terms "aryl" and "arylene" include monocyclic, polycyclic or condensed-ring aromatic groups, the rings may be interrupted by short non-aromatic units, and may contain spiro structures. Aryl groups include but are not limited to phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracenyl, fluorenyl, spirobifluorenyl, etc., and arylene groups include but are not limited to phenylene, biphenylene, terphenylene, naphthyl, phenanthryl, anthracenyl, fluorenyl, spirobifluorenyl, etc.

[0014] In the present application, the term "heteroaryl" includes monocyclic, polycyclic or condensed-ring heteroaryl groups, wherein the rings may be interrupted by short non-aromatic units, wherein the heteroatoms include nitrogen, oxygen, and sulfur, and the heteroaryl groups in the present application include but are not limited to furanyl, phenylthio, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazolyl, pyridyl, pyrazinyl, pyrimid ... pyridyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl , and derivatives thereof; heteroarylene groups include, but are not limited to, furanylene, phenylthioene, pyrrolylene, imidazolylene, pyrazolylene, thiazolylene, thiadiazolylene, isothiazolylene, isoxazolylene, oxazolylene, oxadiazolylene, triazinylene, tetrazinylene, triazolylene, tetrazolylene, furazolylene, pyridinylene, pyrazinylene, pyrimidinylene, pyridazinylene, benzofuranylene, benzothiophenylene, isobenzofuranylene, dibenzofuranylene, Furanyl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, and derivatives thereof. As used in the present invention, the term "substituted" refers to a hydrogen atom in a compound that is replaced by another substituent. The position is not limited to a specific position, as long as the hydrogen at the position can be replaced by a substituent. When two or more substituents are present, the two or more substituents may be the same or different.

[0015] In the present application, the term "halogen" refers to an atom selected from fluorine, chlorine, bromine and iodine.

[0016] In the present application, unless otherwise specified, a hydrogen atom includes protium, deuterium and tritium.

[0017] In the present application, the range of carbon atom number is defined in the definition of the group, and the carbon atom number is any integer within the defined range. For example, C6-C60 aromatic group, the carbon atom number representing the aromatic group can be any integer within the range of 6-60, for example 6, 8, 10, 13, 15, 17, 20, 22, 25, 30, 35, 40, 45, 50, 55 or 60, etc.

[0018] In the present application, unless otherwise specified, a substituent is not fused to the group in which it is located.

[0019] In the present application, if a group is not limited to being substituted or unsubstituted, it means being unsubstituted.

[0020] In this application, Refers to the chemical bonds that connect to other groups.

[0021] In this application, no single bond extending from the ring system is involved in the positioning of the connecting bond. It means that one end of the connecting bond can be connected to any position in the ring system that the bond passes through, and the other end is connected to the rest of the compound molecule.

[0022] In a first aspect, the present invention provides an organic compound having a structure shown in formula (1):

[0023]

[0024] In formula (1),

[0025] Ring A is selected from a C6-C15 aromatic ring, a C3-C15 heteroaromatic ring;

[0026] Ar 2 is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0027] L is selected from a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C3-C60 heteroarylene group;

[0028] R 0 Selected from hydrogen, deuterium, amino, cyano, hydroxyl, thiol, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C1-C60 heteroalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0029] n 1 Any integer selected from 0-5;

[0030] When n 1 When R is greater than or equal to 2, 0 are the same or different, and each R 0 Can exist independently or in any adjacent R 0 They can be bonded to each other to form substituted or unsubstituted C6-C60 aromatic rings, substituted or unsubstituted C3-C60 heteroaromatic rings, such as adjacent hydroxyl groups and phenyl groups can be bonded to a benzofuran ring;

[0031] Ar is selected from the structure shown in formula A or formula B:

[0032]

[0033] In formula A or formula B,

[0034] Z 1 -Z 14 Each is independently selected from CR or N;

[0035] In formula A, Z 1 -Z 6 At least any two of them are selected from N;

[0036] Preferably, in Formula A, Z 1 -Z 6 At least any three of them are selected from N;

[0037] In formula B, Z 7 -Z 14 At least any two of them are selected from N;

[0038] R is selected from hydrogen, deuterium, cyano, hydroxyl, thiol, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C1-C60 heteroalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl,

[0039] Wherein, the substituents in the substituted C6-C60 arylene group, substituted C3-C60 heteroarylene group, substituted C1-C60 alkyl group, substituted C2-C60 alkenyl group, substituted C1-C60 heteroalkyl group, substituted C6-C60 aryl group, substituted C3-C60 heteroaryl group, substituted C6-C60 aromatic ring, substituted C3-C60 heteroaromatic ring are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl group, C3-C60 cycloalkyl group, C6-C60 aryl group, C3-C60 heteroaryl group, C6-C60 aromatic amine group, C3-C60 heteroaromatic amine group.

[0040] Preferably, ring A is selected from a benzene ring, a naphthalene ring, a phenanthrene ring, an anthracene ring, a furan ring, a thiophene ring, a carbazole ring, a benzofuran ring, a benzothiophene ring, a dibenzofuran ring, and a dibenzothiophene ring.

[0041] Preferably, formula (1) is selected from any one of formulas 1-1 to 1-3, wherein L, Ar, n 1 , R 0 ,Ar 2 The definition is the same as that in claim 1:

[0042]

[0043] Preferably, Ar is selected from any one of the structures of Formula A-1, Formula B-1 to Formula B-3:

[0044]

[0045] In formula B-1 or formula B-2, n is selected from any integer from 0 to 5,

[0046] R' is selected from hydrogen, deuterium, cyano, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C1-C60 heteroalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl,

[0047] and when n is greater than or equal to 2, R' is the same or different;

[0048] In formula A-1, Ar 3 ,Ar 4 Each is independently selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group;

[0049] Wherein, the substituents of the substituted C1-C60 alkyl, substituted C1-C60 heteroalkyl, substituted C6-C60 aryl and substituted C3-C60 heteroaryl are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amine and C3-C60 heteroaromatic amine.

[0050] Preferably, the organic compound is selected from any one of the structures of Formula 1-A-1 to Formula 1-A-3 or Formula 1-B-1 to Formula 1-B-9, wherein the definitions of L, n, n1, R0, Ar2, Ar3, Ar4, and R' are the same as those in claim 3:

[0051]

[0052]

[0053] Preferably, Ar 2 is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;

[0054] Wherein, the substituents in the substituted C6-C30 aryl group and the substituted C3-C30 heteroaryl group are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0055] Preferably, L is selected from substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene;

[0056] Wherein, the substituent in the substituted C6-C30 arylene group and the substituted C3-C30 heteroarylene group is selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0057] Preferably, R 0 Selected from hydrogen, deuterium, amino, cyano, hydroxyl, thiol, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;

[0058] n 1 Any integer selected from 0-5;

[0059] When n 1 When R is greater than or equal to 2, 0 are the same or different, and each R 0 Can exist independently or in any adjacent R 0 They may be bonded to each other to form substituted or unsubstituted C6-C30 aromatic rings, substituted or unsubstituted C3-C30 heteroaromatic rings; wherein the substituents in the substituted C1-C30 alkyl, substituted C2-C30 alkenyl, substituted C1-C30 heteroalkyl, substituted C6-C30 aryl, substituted C3-C30 heteroaryl, substituted C6-C30 aromatic ring, substituted C3-C30 heteroaromatic ring are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amine, C3-C60 heteroaromatic amine;

[0060] Preferably, in Formula 1-A-1 to Formula 1-A-3, Ar 3 ,Ar 4 Each is independently selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group;

[0061] Wherein, the substituents in the substituted C6-C30 aryl group and the substituted C3-C30 heteroaryl group are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0062] Preferably, in Formula 1-B-1 to Formula 1-B-9, n is selected from any integer from 0 to 5;

[0063] R' is selected from hydrogen, deuterium, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl,

[0064] and when n is greater than or equal to 2, R' is the same or different;

[0065] Among them, the substituents of the substituted C1-C30 alkyl, substituted C1-C30 heteroalkyl, substituted C6-C30 aryl and substituted C3-C30 heteroaryl are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amine and C3-C60 heteroaromatic amine.

[0066] In an optional embodiment, the substituents of the substituted C6-C30 arylene group, substituted C3-C30 heteroarylene group, substituted C1-C30 alkyl group, substituted C1-C30 heteroalkyl group, substituted C6-C30 aryl group, and substituted C3-C30 heteroaryl group are selected from one or a combination of at least two of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropanyl, cyclohexanyl, cyclopentanyl, phenyl, naphthyl, phenanthrenyl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracenyl, fluorenyl, pyrene, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, carbazolyl, and benzocarbazolyl.

[0067] Preferably, Ar 2 is selected from substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C3-C25 heteroaryl;

[0068] Wherein, the substituents in the substituted C6-C25 aryl group and the substituted C3-C25 heteroaryl group are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0069] Preferably, L is selected from substituted or unsubstituted C6-C25 arylene, substituted or unsubstituted C3-C25 heteroarylene;

[0070] Wherein, the substituents in the substituted C6-C25 arylene group and the substituted C3-C25 heteroarylene group are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0071] Preferably, R 0 Selected from hydrogen, deuterium, amino, cyano, hydroxyl, thiol, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C1-C25 heteroalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C3-C25 heteroaryl;

[0072] n 1 Any integer selected from 0-5;

[0073] When n 1 When R is greater than or equal to 2, 0 are the same or different, and each R 0 Can exist independently or in any adjacent R 0 They may be bonded to each other to form a substituted or unsubstituted C6-C25 aromatic ring, or a substituted or unsubstituted C3-C25 heteroaromatic ring;

[0074] Wherein, the substituents in the substituted C1-C25 alkyl, substituted C2-C25 alkenyl, substituted C1-C25 heteroalkyl, substituted C6-C25 aryl, substituted C3-C25 heteroaryl, substituted C6-C25 aromatic ring, substituted C3-C25 heteroaromatic ring are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amine, C3-C60 heteroaromatic amine;

[0075] Preferably, in Formula 1-A-1 to Formula 1-A-3, Ar 3 ,Ar 4 Each is independently selected from substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C3-C25 heteroaryl;

[0076] Wherein, the substituents in the substituted C6-C25 aryl group and the substituted C3-C25 heteroaryl group are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0077] Preferably, in Formula 1-B-1 to Formula 1-B-9, n is selected from any integer from 0 to 5;

[0078] R' is selected from hydrogen, deuterium, cyano, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C25 heteroalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C3-C25 heteroaryl,

[0079] and when n is greater than or equal to 2, R' is the same or different;

[0080] Among them, the substituents of the substituted C1-C25 alkyl, substituted C1-C25 heteroalkyl, substituted C6-C25 aryl and substituted C3-C25 heteroaryl are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amine and C3-C60 heteroaromatic amine.

[0081] In an optional embodiment, the substituents of the substituted C6-C25 arylene group, substituted C3-C25 heteroarylene group, substituted C1-C25 alkyl group, substituted C1-C25 heteroalkyl group, substituted C6-C25 aryl group, and substituted C3-C25 heteroaryl group are selected from deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropanyl, cyclohexanyl, cyclopentanyl, phenyl, naphthyl, phenanthrenyl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracenyl, fluorenyl, pyrene, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, carbazolyl, and benzocarbazolyl, or a combination of at least two of them.

[0082] Preferably, Ar 2 is selected from substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl;

[0083] Wherein, the substituents in the substituted C6-C20 aryl group and the substituted C3-C20 heteroaryl group are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0084] Preferably, L is selected from substituted or unsubstituted C6-C20 arylene, substituted or unsubstituted C3-C20 heteroarylene;

[0085] Wherein, the substituent in the substituted C6-C20 arylene group and the substituted C3-C20 heteroarylene group is selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0086] Preferably, R 0Selected from hydrogen, deuterium, amino, cyano, hydroxyl, thiol, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl;

[0087] n 1 Any integer selected from 0-5;

[0088] When n 1 When R is greater than or equal to 2, 0 are the same or different, and each R 0 Can exist independently or in any adjacent R 0 They may be bonded to each other to form a substituted or unsubstituted C6-C20 aromatic ring, or a substituted or unsubstituted C3-C20 heteroaromatic ring;

[0089] Wherein, the substituents in the substituted C1-C20 alkyl, substituted C2-C20 alkenyl, substituted C1-C20 heteroalkyl, substituted C6-C20 aryl, substituted C3-C20 heteroaryl, substituted C6-C20 aromatic ring, substituted C3-C20 heteroaromatic ring are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amine, C3-C60 heteroaromatic amine;

[0090] Preferably, in Formula 1-A-1 to Formula 1-A-3, Ar 3 ,Ar 4 Each is independently selected from substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl;

[0091] Wherein, the substituents in the substituted C6-C20 aryl group and the substituted C3-C20 heteroaryl group are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0092] Preferably, in Formula 1-B-1 to Formula 1-B-9, n is selected from any integer from 0 to 5;

[0093] R' is selected from hydrogen, deuterium, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl,

[0094] and when n is greater than or equal to 2, R' is the same or different;

[0095] Wherein, the substituents of the substituted C1-C20 alkyl, substituted C1-C20 heteroalkyl, substituted C6-C20 aryl and substituted C3-C20 heteroaryl are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amine and C3-C60 heteroaromatic amine.

[0096] In an optional embodiment, the substituents of the substituted C6-C20 arylene group, substituted C3-C20 heteroarylene group, substituted C1-C20 alkyl group, substituted C1-C20 heteroalkyl group, substituted C6-C20 aryl group, and substituted C3-C20 heteroaryl group are selected from one or a combination of at least two of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropanyl, cyclohexanyl, cyclopentanyl, phenyl, naphthyl, phenanthrenyl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracenyl, fluorenyl, pyrene, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, carbazolyl, and benzocarbazolyl.

[0097] Preferably, Ar 2 is selected from substituted or unsubstituted C6-C15 aryl, substituted or unsubstituted C3-C15 heteroaryl;

[0098] Wherein, the substituents in the substituted C6-C15 aryl group and the substituted C3-C15 heteroaryl group are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0099] Preferably, L is selected from substituted or unsubstituted C6-C15 arylene, substituted or unsubstituted C3-C15 heteroarylene;

[0100] Wherein, the substituents in the substituted C6-C15 arylene group and the substituted C3-C15 heteroarylene group are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0101] Preferably, R 0 Selected from hydrogen, deuterium, amino, cyano, hydroxyl, thiol, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C2-C15 alkenyl, substituted or unsubstituted C1-C15 heteroalkyl, substituted or unsubstituted C6-C15 aryl, substituted or unsubstituted C3-C15 heteroaryl;

[0102] n1 Any integer selected from 0-5;

[0103] When n 1 When R is greater than or equal to 2, 0 are the same or different, and each R 0 Can exist independently or in any adjacent R 0 They may be bonded to each other to form a substituted or unsubstituted C6-C15 aromatic ring, or a substituted or unsubstituted C3-C15 heteroaromatic ring;

[0104] Wherein, the substituents in the substituted C1-C15 alkyl, substituted C2-C15 alkenyl, substituted C1-C15 heteroalkyl, substituted C6-C15 aryl, substituted C3-C15 heteroaryl, substituted C6-C15 aromatic ring, substituted C3-C15 heteroaromatic ring are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amine, C3-C60 heteroaromatic amine;

[0105] Preferably, in Formula 1-A-1 to Formula 1-A-3, Ar 3 ,Ar 4 Each is independently selected from substituted or unsubstituted C6-C15 aryl, substituted or unsubstituted C3-C15 heteroaryl;

[0106] Wherein, the substituents in the substituted C6-C15 aryl group and the substituted C3-C15 heteroaryl group are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0107] Preferably, in Formula 1-B-1 to Formula 1-B-9, n is selected from any integer from 0 to 5;

[0108] R' is selected from hydrogen, deuterium, cyano, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C1-C15 heteroalkyl, substituted or unsubstituted C6-C15 aryl, substituted or unsubstituted C3-C15 heteroaryl,

[0109] and when n is greater than or equal to 2, R' is the same or different;

[0110] Among them, the substituents of the substituted C1-C15 alkyl, substituted C1-C15 heteroalkyl, substituted C6-C15 aryl and substituted C3-C15 heteroaryl are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amine and C3-C60 heteroaromatic amine.

[0111] In an optional embodiment, the substituents of the substituted C6-C15 arylene group, substituted C3-C15 heteroarylene group, substituted C1-C15 alkyl group, substituted C1-C15 heteroalkyl group, substituted C6-C15 aryl group, and substituted C3-C15 heteroaryl group are selected from one or a combination of at least two of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexane, cyclopentanyl, phenyl, naphthyl, phenanthrenyl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracenyl, fluorenyl, pyrene, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, carbazolyl, and benzocarbazolyl.

[0112] Preferably, Ar 2 is selected from substituted or unsubstituted A groups, wherein the A groups are selected from phenyl, naphthyl, phenanthryl, anthracenyl, fluoranthenyl, pyrenyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothienyl, dibenzothienyl, naphthobenzothienyl, carbazolyl, phenylcarbazolyl, benzocarbazolyl, benzophenylcarbazolyl, dibenzocarbazolyl, biphenylcarbazolyl, benzoxazolyl, naphthoxazolyl, phenanthroxazolyl, phenanthrobenzofuranyl, benzofuranobenzofuranyl, phenylcarbazolyl;

[0113] Wherein, the substituent in the substituted A group is selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0114] Preferably, the substituent in the substituted A group is selected from one or a combination of at least two of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexane, cyclopentane, phenyl, naphthyl, phenanthrenyl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracenyl, fluorenyl, pyrenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, carbazolyl, and benzocarbazolyl;

[0115] Preferably, L is selected from substituted or unsubstituted B groups;

[0116] The B group is selected from phenylene, naphthylene, phenanthrylene, binaphthylene, dibenzofuranylene, dibenzothiophenylene, benzonaphthofuranylene, benzonaphthothiophenylene;

[0117] Wherein, the substituent in the substituted B group is selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0118] Preferably, the substituent in the substituted B group is selected from one or a combination of at least two of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropyl, cyclohexyl, cyclopentyl, phenyl, naphthyl, phenanthryl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracenyl, fluorenyl, pyrenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, carbazolyl, and benzocarbazolyl;

[0119] Preferably, n 1 Any integer selected from 0-5;

[0120] R 0 is selected from hydrogen, deuterium, amino, cyano, hydroxyl, mercapto, a substituted or unsubstituted C group, wherein the C group is selected from methyl, ethyl, propyl, 1-butyl, 2-butyl, 3-butyl, adamantyl, cyclopropyl, cyclopentyl, cyclobutane, cyclohexyl, vinyl, propenyl, methoxy, methylthio, ethoxy, ethylthio, aldehyde, aminomethyl, methylamino, phenyl, naphthyl, phenanthryl, anthracenyl, fluoranthenyl, pyrenyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzodimethylfluorenyl, phenyl diphenylfluorenyl, benzospirobifluorenyl, furanyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, thienyl, benzothienyl, dibenzothienyl, naphthobenzothienyl, pyridyl, pyrrolyl, pyrimidinyl, oxazolyl, isoxazolyl, quinolyl, isoquinolyl, carbazolyl, phenylcarbazolyl, benzocarbazolyl, benzophenylcarbazolyl, dibenzocarbazolyl, biphenylcarbazolyl, benzoxazolyl, naphthoxazolyl, phenanthroxazolyl, phenanthrobenzofuranyl, benzofuranobenzofuranyl, phenylcarbazolyl;

[0121] Wherein, the substituent of the substituted C group is selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0122] Preferably, the substituent of the substituted C group is selected from one or a combination of at least two of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropyl, cyclohexyl, cyclopentyl, phenyl, naphthyl, phenanthrenyl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracenyl, fluorenyl, pyrenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, carbazolyl, benzocarbazolyl;

[0123] When n 1 When R is greater than or equal to 2, 0 are the same or different, and each R 0 Can exist independently or in any adjacent R 0 They may be bonded to each other to form a substituted or unsubstituted A ring;

[0124] The A ring is selected from a benzene ring, a naphthalene ring, a phenanthrene ring, an anthracene ring, a fluoranthene ring, a pyrene ring, a biphenyl ring, a terphenyl ring, a phenylnaphthalene ring, a naphthylbenzene ring, a triphenylene ring, a fluorene ring, a dimethylfluorene ring, a diphenylfluorene ring, a spirobifluorene ring, a benzodimethylfluorene ring, a benzodiphenylfluorene ring, a benzospirobifluorene ring, a benzofuran ring, a dibenzofuran ring, a naphthobenzofuran ring, a dinaphthofuran ring, a benzothiophene ring, a dibenzothiophene ring, a naphthobenzothiophene ring, a carbazole ring, a phenylcarbazole ring, a benzocarbazole ring, a benzophenylcarbazole ring, a dibenzocarbazole ring, a biphenylcarbazole ring, a benzoxazole ring, a naphthoxazole ring, a phenanthreneoxazole ring, a phenanthrenebenzofuran ring, a benzofuranbenzofuran ring, and a phenylcarbazolebenzofuran ring;

[0125] Wherein, the substituent in the substituted A ring is selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amine, and C3-C60 heteroaromatic amine;

[0126] Preferably, the substituent in the substituted A ring is selected from one or a combination of at least two of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexane, cyclopentane, phenyl, naphthyl, phenanthrenyl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracenyl, fluorenyl, pyrenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, carbazolyl, and benzocarbazolyl;

[0127] Preferably, in formula (1), Can be selected from the group consisting of:

[0128]

[0129] Preferably, in Formula 1-A-1 to Formula 1-A-3, Ar 3 ,Ar 4 each independently selected from substituted or unsubstituted A groups; the A groups are selected from phenyl, naphthyl, phenanthryl, anthracenyl, fluoranthenyl, pyrenyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothienyl, dibenzothienyl, naphthobenzothienyl, carbazolyl, phenylcarbazolyl, benzocarbazolyl, benzophenylcarbazolyl, dibenzocarbazolyl, biphenylcarbazolyl, benzoxazolyl, naphthoxazolyl, phenanthroxazolyl, phenanthrobenzofuranyl, benzofuranobenzofuranyl, phenylcarbazolyl;

[0130] Wherein, the substituent in the substituted A group is selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0131] Preferably, the substituent in the substituted A group is selected from one or a combination of at least two of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexane, cyclopentane, phenyl, naphthyl, phenanthrenyl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracenyl, fluorenyl, pyrenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, carbazolyl, and benzocarbazolyl;

[0132] Preferably, in Formula 1-B-1 to Formula 1-B-9, n is selected from any integer of 0-5,

[0133] R' is selected from hydrogen, deuterium, cyano, substituted or unsubstituted D groups, and when n is greater than or equal to 2, R' is the same or different; D groups are selected from methyl, ethyl, propyl, primary butyl, secondary butyl, tert-butyl, adamantyl, cyclopropyl, cyclopentyl, cyclobutane, cyclohexyl, methoxy, methylthio, ethoxy, ethylthio, aldehyde, aminomethyl, methylamino, phenyl, naphthyl, phenanthryl, anthracenyl, fluoranthenyl, pyrenyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzodimethylfluorenyl , benzodiphenylfluorenyl, benzospirobifluorenyl, furanyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, thienyl, benzothienyl, dibenzothienyl, naphthobenzothienyl, pyridyl, pyrrolyl, pyrimidinyl, oxazolyl, isoxazolyl, quinolyl, isoquinolyl, carbazolyl, phenylcarbazolyl, benzocarbazolyl, benzophenylcarbazolyl, dibenzocarbazolyl, biphenylcarbazolyl, benzoxazolyl, naphthoxazolyl, phenanthroxazolyl, phenanthrobenzofuranyl, benzofuranobenzofuranyl, phenylcarbazolyl;

[0134] Wherein, the substituent of the substituted D group is selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0135] Preferably, the substituent of the substituted D group is selected from one or a combination of at least two of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexane, cyclopentane, phenyl, naphthyl, phenanthrenyl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracenyl, fluorenyl, pyrenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, carbazolyl, and benzocarbazolyl.

[0136] Preferably, the compound is selected from the following structures:

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149] Optionally, the deuteration rate of the above-mentioned compound is 0%-100%.

[0150] In a second aspect, the present invention also provides a method for preparing the above-mentioned organic compound, which is as follows:

[0151] Synthesis of intermediate sub-4-n:

[0152]

[0153] Synthesis of compound Nn:

[0154]

[0155] The raw materials AX, BX, CX, DX and EX can be directly purchased or synthesized by conventional reaction pathways and conditions with reference to existing literature reports.

[0156] In a third aspect, the present invention further provides an organic electroluminescent material comprising the organic compound as described above.

[0157] In a fourth aspect, the present invention further provides an organic electroluminescent device, comprising a cathode, an anode and an organic layer located between the cathode and the anode, wherein the organic layer comprises the above-mentioned organic compound or the above-mentioned organic electroluminescent material.

[0158] Preferably, the organic layer located between the cathode and the anode includes any one or a combination of at least two of a hole injection layer, a hole transport layer, a luminescence auxiliary layer, a luminescent layer, a hole blocking layer, an electron transport layer and an electron injection layer.

[0159] 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 can be made of benzidine derivatives, arylamine compounds, phthalocyanine derivatives or other materials, and this application does not impose any special restrictions on this. The materials of the hole injection layer include but are not limited to the following compounds:

[0160]

[0161] Optionally, the organic layer includes a hole transport layer, which may include one or more hole transport materials, and the hole transport material may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds, and the present application does not impose any special restrictions on this. The materials of the hole injection layer include but are not limited to the following compounds:

[0162]

[0163]

[0164] Optionally, the organic layer includes a light-emitting auxiliary layer, and the light-emitting auxiliary layer may be a single-layer or multi-layer structure.

[0165] Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises an organic compound as represented by formula (1) or the organic electroluminescent material as described above.

[0166] Preferably, the light-emitting layer includes a host material and a guest material, the host material includes the organic compound as described above or the host material in the organic electroluminescent material as described above, and the guest material can be a compound with a condensed aromatic ring or a derivative thereof, a compound with a heteroaromatic ring or a derivative thereof, an aromatic amine derivative or other material, and the present application does not impose any special restrictions on this. The guest material is also called a doping material or a dopant. According to the type of light emission, it can be divided into a fluorescent dopant and a phosphorescent dopant. Specific examples of the phosphorescent dopant include, but are not limited to, the following structures:

[0167]

[0168]

[0169] Optionally, the organic layer includes a hole blocking layer, and the hole blocking layer may be a single-layer or multi-layer structure.

[0170] Optionally, the organic layer includes an electron transport layer, which may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, which may be selected from but not limited to LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives or other electron transport materials, and the present application does not make any special restrictions on this. The materials of the electron transport layer include but are not limited to the following structures:

[0171]

[0172]

[0173] 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 may include a complex of alkali metals and organic matter.

[0174] In a fifth aspect, the present invention further provides an electronic device, characterized in that the electronic device comprises the organic electroluminescent device as described above or the organic electroluminescent material as described above or the organic compound as shown in formula (1).

[0175] The electronic devices include, but are not limited to, mobile phones, wearable watches, optical fiber devices, lighting equipment, electronic photographic photosensitive body devices, photoelectric converters, organic solar cells, switching element devices, organic light-emitting field effect transistors, image sensors or dye lasers, etc.

[0176] The above can be combined freely.

[0177] Beneficial effects of the present invention:

[0178] The organic compound provided by the present invention is obtained by introducing a substituent Ar into the ring A of formula (1). 2 , the substituent Ar of the compound represented by formula (1) can be 2 The compound produces a better conjugation effect with the carbazole fragment, thereby significantly improving the electron donating ability of the donor fragment of the compound, and can effectively enhance the intramolecular dipole moment of the compound, thereby accelerating the intramolecular exciton transfer and recombination, and thus making the organic electroluminescent device containing the organic compound have a lower driving voltage, higher luminous efficiency and longer life. BRIEF DESCRIPTION OF THE DRAWINGS

[0179] In order to more clearly illustrate the specific implementation methods of the present invention or the technical solutions in the prior art, the drawings required for use in the specific implementation methods or the description of the prior art will be briefly introduced below. Obviously, the drawings described below are some implementation methods of the present invention. For ordinary technicians in this field, other drawings can be obtained based on these drawings without paying creative work.

[0180] Figure 1 A structural diagram of an organic electroluminescent device in an embodiment of the device of the present invention;

[0181] 1-substrate; 2-anode; 3-hole injection layer; 4-hole transport layer; 5-light-emitting layer; 6-electron transport layer; 7-electron injection layer; 8-cathode. DETAILED DESCRIPTION

[0182] If no specific experimental steps or conditions are specified in the examples, the conventional experimental steps or conditions described in the literature in the field can be used. If no manufacturer is specified for the reagents or instruments used, they are all conventional reagent products that can be obtained commercially.

[0183] Those skilled in the art will recognize that the chemical reactions described herein can be used to appropriately prepare many of the heterocyclic compounds of the present invention, and that other methods for preparing the compounds of the present invention are considered to be within the scope of the present invention. For example, the synthesis of the compounds not exemplified herein can be successfully accomplished by those skilled in the art by modification methods, such as appropriate protection of interfering groups, by utilizing other known reagents in addition to those described herein, or by making some conventional modifications to the reaction conditions. The compounds for which the synthesis methods are not mentioned in the present invention are all raw materials obtained from commercial sources.

[0184] If no specific experimental steps or conditions are specified in the examples, the conventional experimental steps or conditions described in the literature in the field can be used. If no manufacturer is specified for the reagents or instruments used, they are all conventional reagent products that can be obtained commercially.

[0185] Those skilled in the art will recognize that the chemical reactions described herein can be used to appropriately prepare many of the heterocyclic compounds of the present invention, and that other methods for preparing the compounds of the present invention are considered to be within the scope of the present invention. For example, the synthesis of the compounds not exemplified herein can be successfully accomplished by those skilled in the art by modification methods, such as appropriate protection of interfering groups, by utilizing other known reagents in addition to those described herein, or by making some conventional modifications to the reaction conditions. The compounds for which the synthesis methods are not mentioned in the present invention are all raw materials obtained from commercial sources.

[0186] The specific structures of the raw materials ax, bx, cx, dx, and ex used in the embodiments of the present invention are as follows:

[0187] In the embodiment of the present invention, the raw material ax comprises the following structure:

[0188]

[0189] In the embodiment of the present invention, the raw material bx comprises the following structure:

[0190]

[0191] In the embodiment of the present invention, the raw material cx comprises the following structure:

[0192]

[0193] In the embodiment of the present invention, the raw material dx comprises the following structure:

[0194]

[0195] In the embodiment of the present invention, the raw material ex comprises the following structure:

[0196]

[0197] Synthesis of intermediate sub-n-4:

[0198] Synthesis of intermediate sub-1-4:

[0199]

[0200] Synthesis of intermediate sub-1-1: Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material a-1 (1.1 mmol), raw material b-1 (1.0 mmol), Pd(PPh) in sequence. 2 Cl 2 (0.03mmol), potassium carbonate (2.5mmol), toluene / water (10mL / 2mL), heated to 90℃ for 5h, cooled to room temperature after the reaction, quenched with saturated aqueous ammonium chloride solution, extracted with ethyl acetate, the organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporator. The crude product was separated by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain the intermediate sub-1-1 (yield 88%).

[0201] Synthesis of intermediate sub-1-2: Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw materials c-1 (1.0 mmol), d-1 (1.1 mmol), Pd(dppf)Cl 2 (0.03mmol), potassium carbonate (2.5mmol), 1,4-dioxane / water (10mL / 2mL), heated to 90℃ for 5h, cooled to room temperature after the reaction, quenched with saturated aqueous ammonium chloride solution, extracted with ethyl acetate, the organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporator. The crude product was separated by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain the intermediate sub-1-2 (yield 82%).

[0202] Synthesis of intermediate sub-1-3: Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add intermediate sub-1-1 (1 mmol), intermediate sub-1-2 (1.1 mmol), tris(dibenzylideneacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), toluene (10 mL) in sequence, raise the temperature to 110 ° C and react for 5 hours. After the reaction is completed, cool to room temperature, filter, rinse the filter cake twice with deionized water and twice with ethanol, and then purify the crude product by recrystallization with toluene and tetrahydrofuran twice to obtain compound sub-1-3 (yield 70%).

[0203] Synthesis of intermediate sub-1-4: Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add intermediate sub-1-3 (1 mmol), bipyralidinol (1.2 mmol), Pd(dppf)Cl 2 (0.03mmol), potassium carbonate (2.5mmol), 1,4-dioxane / water (10mL / 2mL), heated to 90℃ for 5h, cooled to room temperature after the reaction, quenched with saturated aqueous ammonium chloride solution, extracted with ethyl acetate, the organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporator. The crude product was separated by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain the intermediate sub-1-4 (yield 84%).

[0204] Synthesis of intermediate sub-3-4:

[0205]

[0206] Synthesis of intermediate sub-3-1: The synthesis steps of intermediate sub-3-1 are the same as those of intermediate sub-1-1, except that raw material a-1 is replaced by raw material a-3 to obtain intermediate sub-3-1 (yield 85%).

[0207] Synthesis of intermediate sub-3-2: The synthesis steps of intermediate sub-3-2 are the same as those of intermediate sub-1-2, except that raw material d-1 is replaced by raw material d-2 to obtain intermediate sub-3-2 (yield 83%).

[0208] Synthesis of intermediate sub-3-3: The synthesis steps of intermediate sub-3-3 are the same as those of intermediate sub-1-3, except that intermediate sub-1-1 is replaced by intermediate sub-3-1, and intermediate sub-1-2 is replaced by sub-3-2, to obtain intermediate sub-3-3 (yield 71%).

[0209] Synthesis of intermediate sub-3-4: The synthesis steps of intermediate sub-3-4 are the same as those of intermediate sub-1-4, except that intermediate sub-1-3 is replaced by intermediate sub-3-3 to obtain intermediate sub-3-4 (yield 83%).

[0210] Synthesis of intermediate sub-18-4:

[0211]

[0212] Synthesis of intermediate sub-18-1: The synthesis steps of intermediate sub-18-1 are the same as those of intermediate sub-1-1, except that raw material a-1 is replaced by raw material a-2 to obtain intermediate sub-18-1 (yield 81%).

[0213] Synthesis of intermediate sub-18-2: The synthesis steps of intermediate sub-18-2 are the same as those of intermediate sub-1-2, except that raw material c-1 is replaced by raw material c-2, and raw material d-1 is replaced by raw material d-2, thereby obtaining intermediate sub-18-2 (yield 84%).

[0214] Synthesis of intermediate sub-18-3: The synthesis steps of intermediate sub-18-3 are the same as those of intermediate sub-1-3, except that intermediate sub-1-1 is replaced by intermediate sub-18-1, and intermediate sub-1-2 is replaced by sub-18-2, to obtain intermediate sub-18-3 (yield 69%).

[0215] Synthesis of intermediate sub-18-4: The synthesis steps of intermediate sub-18-4 are the same as those of intermediate sub-1-4, except that intermediate sub-1-3 is replaced by intermediate sub-18-3 to obtain intermediate sub-18-4 (yield 84%).

[0216] Synthesis of intermediate sub-45-4:

[0217]

[0218] Synthesis of intermediate sub-45-1: The synthesis steps of intermediate sub-45-1 are the same as those of intermediate sub-1-1, except that raw material a-1 is replaced by raw material a-3, and raw material b-1 is replaced by raw material b-3, thereby obtaining intermediate sub-45-1 (yield 80%).

[0219] Synthesis of intermediate sub-45-2: The synthesis steps of intermediate sub-45-2 are the same as those of intermediate sub-1-2, except that raw material d-1 is replaced by raw material d-3 to obtain intermediate sub-45-2 (yield 83%).

[0220] Synthesis of intermediate sub-45-3: The synthesis steps of intermediate sub-45-3 are the same as those of intermediate sub-1-3, except that intermediate sub-1-1 is replaced by intermediate sub-45-1, and intermediate sub-1-2 is replaced by sub-45-2, to obtain intermediate sub-45-3 (yield 71%).

[0221] Synthesis of intermediate sub-45-4: The synthesis steps of intermediate sub-45-4 are the same as those of intermediate sub-1-4, except that intermediate sub-1-3 is replaced by intermediate sub-45-3 to obtain intermediate sub-45-4 (yield 85%).

[0222] Synthesis of intermediate sub-62-4:

[0223]

[0224] Synthesis of intermediate sub-62-1: The synthesis steps of intermediate sub-62-1 are the same as those of intermediate sub-1-1, except that raw material a-1 is replaced by raw material a-4 to obtain intermediate sub-62-1 (yield 84%).

[0225] Synthesis of intermediate sub-62-2: The synthesis steps of intermediate sub-62-2 are the same as those of intermediate sub-1-2, except that raw material c-1 is replaced by raw material c-3, and raw material d-1 is replaced by raw material d-2, thereby obtaining intermediate sub-62-2 (yield 83%).

[0226] Synthesis of intermediate sub-62-3: The synthesis steps of intermediate sub-62-3 are the same as those of intermediate sub-1-3, except that intermediate sub-1-1 is replaced by intermediate sub-62-1, and intermediate sub-1-2 is replaced by sub-62-2, to obtain intermediate sub-62-3 (yield 70%).

[0227] Synthesis of intermediate sub-62-4: The synthesis steps of intermediate sub-62-4 are the same as those of intermediate sub-1-4, except that intermediate sub-1-3 is replaced by intermediate sub-62-3 to obtain intermediate sub-62-4 (yield 82%).

[0228] Synthesis of intermediate sub-74-4:

[0229]

[0230] Synthesis of intermediate sub-74-1: The synthesis steps of intermediate sub-74-1 are the same as those of intermediate sub-1-1, except that raw material a-1 is replaced by raw material a-5 to obtain intermediate sub-74-1 (yield 78%).

[0231] Synthesis of intermediate sub-74-2: The synthesis steps of intermediate sub-74-2 are the same as those of intermediate sub-1-2, except that raw material c-1 is replaced by raw material c-4 to obtain intermediate sub-74-2 (yield 82%).

[0232] Synthesis of intermediate sub-74-3: The synthesis steps of intermediate sub-74-3 are the same as those of intermediate sub-1-3, except that intermediate sub-1-1 is replaced by intermediate sub-74-1, and intermediate sub-1-2 is replaced by sub-74-2, thereby obtaining intermediate sub-74-3 (yield 72%).

[0233] Synthesis of intermediate sub-74-4: The synthesis steps of intermediate sub-74-4 are the same as those of intermediate sub-1-4, except that intermediate sub-1-3 is replaced by intermediate sub-74-3 to obtain intermediate sub-74-4 (yield 81%).

[0234] Synthesis of intermediate sub-136-4:

[0235]

[0236] Synthesis of intermediate sub-136-2: The synthesis steps of intermediate sub-136-2 are the same as those of intermediate sub-1-2, except that raw material c-1 is replaced by raw material c-5, and raw material d-1 is replaced by raw material d-4, thereby obtaining intermediate sub-136-2 (yield 80%).

[0237] Synthesis of intermediate sub-136-3: The synthesis steps of intermediate sub-136-3 are the same as those of intermediate sub-1-3, except that intermediate sub-1-2 is replaced by sub-136-2 to obtain intermediate sub-136-3 (yield 68%).

[0238] Synthesis of intermediate sub-136-4: The synthesis steps of intermediate sub-136-4 are the same as those of intermediate sub-1-4, except that intermediate sub-1-3 is replaced by intermediate sub-136-3 to obtain intermediate sub-136-4 (yield 83%).

[0239] Synthesis of intermediate sub-163-4:

[0240]

[0241] Synthesis of intermediate sub-163-1: The synthesis steps of intermediate sub-163-1 are the same as those of intermediate sub-1-1, except that raw material b-1 is replaced by raw material b-4 to obtain intermediate sub-163-1 (yield 84%).

[0242] Synthesis of intermediate sub-163-3: The synthesis steps of intermediate sub-163-3 are the same as those of intermediate sub-1-3, except that intermediate sub-1-1 is replaced by intermediate sub-163-1, and intermediate sub-1-2 is replaced by sub-18-2, thereby obtaining intermediate sub-163-3 (yield 71%).

[0243] Synthesis of intermediate sub-163-4: The synthesis steps of intermediate sub-163-4 are the same as those of intermediate sub-1-4, except that intermediate sub-1-3 is replaced by intermediate sub-163-3 to obtain intermediate sub-163-4 (yield 82%).

[0244] Synthesis of intermediate sub-167-4:

[0245]

[0246] Synthesis of intermediate sub-167-2: The synthesis steps of intermediate sub-167-2 are the same as those of intermediate sub-1-2, except that raw material c-1 is replaced by raw material c-6, and raw material d-1 is replaced by raw material d-2, thereby obtaining intermediate sub-167-2 (yield 83%).

[0247] Synthesis of intermediate sub-167-3: The synthesis steps of intermediate sub-167-3 are the same as those of intermediate sub-1-3, except that intermediate sub-1-1 is replaced by intermediate sub-3-1, and intermediate sub-1-2 is replaced by sub-167-2, thereby obtaining intermediate sub-167-3 (yield 70%).

[0248] Synthesis of intermediate sub-167-4: The synthesis steps of intermediate sub-167-4 are the same as those of intermediate sub-1-4, except that intermediate sub-1-3 is replaced by intermediate sub-167-3 to obtain intermediate sub-167-4 (yield 80%).

[0249] Synthesis of intermediate sub-177-4:

[0250]

[0251] Synthesis of intermediate sub-177-1: The synthesis steps of intermediate sub-177-1 are the same as those of intermediate sub-1-1, except that raw material a-1 is replaced by raw material a-5, and raw material b-1 is replaced by raw material b-3, thereby obtaining intermediate sub-177-1 (yield 83%).

[0252] Synthesis of intermediate sub-177-2: The synthesis steps of intermediate sub-177-2 are the same as those of intermediate sub-1-2, except that raw material c-1 is replaced by raw material c-4, and raw material d-1 is replaced by raw material d-5, to obtain intermediate sub-177-2 (yield 80%).

[0253] Synthesis of intermediate sub-177-3: The synthesis steps of intermediate sub-177-3 are the same as those of intermediate sub-1-3, except that intermediate sub-1-1 is replaced by intermediate sub-177-1, and intermediate sub-1-2 is replaced by sub-177-2, to obtain intermediate sub-177-3 (yield 71%).

[0254] Synthesis of intermediate sub-177-4: The synthesis steps of intermediate sub-177-4 are the same as those of intermediate sub-1-4, except that intermediate sub-1-3 is replaced by intermediate sub-177-3 to obtain intermediate sub-177-4 (yield 82%).

[0255] Synthesis of intermediate sub-229-4:

[0256]

[0257] Synthesis of intermediate sub-229-1: The synthesis steps of intermediate sub-229-1 are the same as those of intermediate sub-1-1, except that raw material a-1 is replaced by raw material a-6 to obtain intermediate sub-229-1 (yield 82%).

[0258] Synthesis of intermediate sub-229-2: The synthesis steps of intermediate sub-229-2 are the same as those of intermediate sub-1-2, except that raw material c-1 is replaced by raw material c-5, and raw material d-1 is replaced by raw material d-2, thereby obtaining intermediate sub-229-2 (yield 80%).

[0259] Synthesis of intermediate sub-229-3: The synthesis steps of intermediate sub-229-3 are the same as those of intermediate sub-1-3, except that intermediate sub-1-1 is replaced by intermediate sub-229-1, and intermediate sub-1-2 is replaced by sub-229-2, to obtain intermediate sub-229-3 (yield 70%).

[0260] Synthesis of intermediate sub-229-4: The synthesis steps of intermediate sub-229-4 are the same as those of intermediate sub-1-4, except that intermediate sub-1-3 is replaced by intermediate sub-229-3 to obtain intermediate sub-229-4 (yield 83%).

[0261] Synthesis of intermediate sub-273-4:

[0262]

[0263] Synthesis of intermediate sub-273-2: The synthesis steps of intermediate sub-273-2 are the same as those of intermediate sub-1-2, except that raw material c-1 is replaced by raw material c-7 to obtain intermediate sub-273-2 (yield 82%).

[0264] Synthesis of intermediate sub-273-3: The synthesis steps of intermediate sub-273-3 are the same as those of intermediate sub-1-3, except that intermediate sub-1-1 is replaced by intermediate sub-74-1, and intermediate sub-1-2 is replaced by sub-273-2, thereby obtaining intermediate sub-273-3 (yield 72%).

[0265] Synthesis of intermediate sub-273-4: The synthesis steps of intermediate sub-273-4 are the same as those of intermediate sub-1-4, except that intermediate sub-1-3 is replaced by intermediate sub-273-3 to obtain intermediate sub-273-4 (yield 81%).

[0266] Synthesis of intermediate sub-330-4:

[0267]

[0268] Synthesis of intermediate sub-330-1: The synthesis steps of intermediate sub-330-1 are the same as those of intermediate sub-1-1, except that raw material b-1 is replaced by raw material b-2 to obtain intermediate sub-330-1 (yield 85%).

[0269] Synthesis of intermediate sub-330-2: The synthesis steps of intermediate sub-330-2 are the same as those of intermediate sub-1-2, except that raw material c-1 is replaced by raw material c-6, and raw material d-1 is replaced by raw material d-4, thereby obtaining intermediate sub-330-2 (yield 80%).

[0270] Synthesis of intermediate sub-330-3: The synthesis steps of intermediate sub-330-3 are the same as those of intermediate sub-1-3, except that intermediate sub-1-1 is replaced by intermediate sub-330-1, and intermediate sub-1-2 is replaced by sub-330-2, thereby obtaining intermediate sub-330-3 (yield 72%).

[0271] Synthesis of intermediate sub-330-4: The synthesis steps of intermediate sub-330-4 are the same as those of intermediate sub-1-4, except that intermediate sub-1-3 is replaced by intermediate sub-330-3 to obtain intermediate sub-330-4 (yield 81%).

[0272] Synthesis of intermediate sub-359-4:

[0273]

[0274] Synthesis of intermediate sub-359-3: The synthesis steps of intermediate sub-359-3 are the same as those of intermediate sub-1-3, except that intermediate sub-1-2 is replaced by sub-74-2 to obtain intermediate sub-359-3 (yield 70%).

[0275] Synthesis of intermediate sub-359-4: The synthesis steps of intermediate sub-359-4 are the same as those of intermediate sub-1-4, except that intermediate sub-1-3 is replaced by intermediate sub-359-3 to obtain intermediate sub-359-4 (yield 84%).

[0276] Synthesis of intermediate sub-360-4

[0277]

[0278] Synthesis of intermediate sub-360-3: The synthesis steps of intermediate sub-360-3 are the same as those of intermediate sub-1-3, except that intermediate sub-1-1 is replaced by sub-74-1, and intermediate sub-1-2 is replaced by sub-229-2, to obtain intermediate sub-360-3 (yield 70%).

[0279] Synthesis of intermediate sub-360-4: The synthesis steps of intermediate sub-360-4 are the same as those of intermediate sub-1-4, except that intermediate sub-1-3 is replaced by intermediate sub-360-3 to obtain intermediate sub-360-4 (yield 82%).

[0280] Synthesis Example

[0281] This synthesis example provides the synthesis of compound Nn:

[0282]

[0283] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add the intermediate sub-1-4 (1 mmol), raw material e-1 (1.2 mmol), Pd(dppf)Cl 2 (0.03mmol), potassium carbonate (2.5mmol), 1,4-dioxane / water (10mL / 2mL), heated to 90℃ for reaction for 5h. After the reaction, cooled to room temperature, filtered, rinsed the filter cake twice with deionized water and twice with ethanol. The crude product was purified by recrystallization with o-dichlorobenzene twice to obtain compound N-1 (yield 65%).

[0284] Elemental analysis: C 53 H 34 N 4 ; Theoretical value: C, 87.58; H, 4.71; N, 7.71; Found: C, 87.55; H, 4.72; N, 7.73; HRMS (ESI) m / z [M+H] + : Theoretical value: 726.88; measured value: 727.85.

[0285] Referring to the above synthesis method, by replacing the intermediates sub-n-4 and ex, a series of compounds Nn can be obtained. The structures of the compounds provided in the synthesis examples of the present invention are shown in Table 1:

[0286] Table 1

[0287]

[0288]

[0289]

[0290]

[0291]

[0292] The elemental analysis results of the compounds in Table 1 are shown in Table 2 below:

[0293] Table 2

[0294]

[0295] Device Embodiment

[0296] The present invention also provides an OLED device composed of different organic electroluminescent materials, the specific structure distribution is as follows: Figure 1 As shown, the OLED device has the following layer structure: substrate (glass substrate) 1 / anode 2 (indium tin oxide (ITO) coating coated on the glass substrate) / hole injection layer 3 (HIL) / hole transport layer 4 (HTL) / light-emitting layer 5 (EML) / electron transport layer 6 (ETL) / electron injection layer (EIL) 7 / cathode 8.

[0297] The preparation method of the OLED device comprises the following steps:

[0298] (1) Substrate cleaning:

[0299] The glass substrate coated with transparent ITO is 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 the water is completely removed, and then cleaned with ultraviolet light and ozone.

[0300] (2) Evaporation of organic light-emitting functional layer:

[0301] The glass substrate with the anode layer is placed in a vacuum chamber and evacuated to 1×10 -6 Up to 2×10 -4 Pa, vacuum evaporating a mixture of HI-9 and HT-9 on the above anode layer film, wherein the mass ratio of HI-9 to HT-9 is 3:97, as a hole injection layer, the evaporation thickness is 10 nm;

[0302] A hole transport layer (made of HT-9) is evaporated on the hole injection layer, with a thickness of 80 nm.

[0303] The light-emitting layer is deposited on the hole transport layer. The specific preparation method is: vacuum-deposit the light-emitting host material (the materials are shown in Table 3) and the guest material RD-4 in a co-evaporation manner, and the total film thickness of the deposition is 35 nm;

[0304] An electron transport layer is evaporated on the light-emitting layer. The specific preparation method is: vacuum evaporation of ET-4 and LiQ in a co-evaporation manner, wherein the mass ratio of ET-4 to LiQ is 50:50, and the total evaporation film thickness is 30 nm;

[0305] An electron injection layer (made of LiQ) is vacuum-deposited on the electron transport layer, with a total film thickness of 1 nm.

[0306] Al was evaporated on the electron injection layer, and the total film thickness of the evaporated layer was 90 nm.

[0307] The material structures mainly used in the device embodiments and comparative examples are as follows:

[0308]

[0309] Parameters such as materials and thickness of each layer in device embodiments 1-17 and device comparative examples 1-3 are shown in Table 3 below:

[0310] Table 3

[0311]

[0312]

[0313]

[0314]

[0315] The organic electroluminescent devices obtained from device examples 1-17 and device comparative examples 1-3 were tested.

[0316] Instruments: The device's current, voltage, brightness, luminous spectrum and other characteristics are tested synchronously using a PR650 spectrum scanning luminance meter and a Keithley K2400 digital source meter system;

[0317] Test conditions: Photoelectric properties Test conditions: Current density is 10mA / cm 2 .

[0318] Life test: current density is 50mA / cm 2 , record the time (in hours) when the device brightness drops to 95% of the original brightness.

[0319] The device performance test results are shown in Table 4, wherein the device life test data of Comparative Example 1 in Table 4 is set to 100, and the device life data in Table 4 are all ratios thereof:

[0320] Table 4

[0321] project Driving voltage(V) Current efficiency (Cd / A) Lifespan T95 Device Example 1 3.52 24.81 118.2 Device Example 2 3.58 25.10 119.4 Device Example 3 3.57 24.84 118.8 Device Example 4 3.51 24.57 119.0 Device Example 5 3.55 24.67 120.3 Device Example 6 3.55 25.07 117.9 Device Example 7 3.60 24.91 119.4 Device Example 8 3.54 25.32 118.9 Device Example 9 3.53 24.59 117.6 Device Example 10 3.54 24.63 118.4 Device Example 11 3.62 25.11 119.5 Device Example 12 3.64 24.86 121.2 Device Example 13 3.61 25.10 118.9 Device Example 14 3.62 24.68 119.7 Device Example 15 3.61 24.77 119.8 Device Example 16 3.64 24.49 118.5 Device Example 17 3.55 25.36 119.3 Device Comparison Example 1 3.98 20.45 100 Device Comparison Example 2 3.92 21.20 110.3 Device Comparison Example 3 3.89 20.81 107.6

[0322] The present invention introduces a substituent Ar into the ring A of formula (1). 2 The compound design shows that compared with the direct introduction of substituents on the carbazole fragment, the compound shown in formula (1) can make the substituent Ar 2 It produces a better conjugation effect with the carbazole fragment, thereby significantly improving the electron donating ability of the donor fragment of the single host material of the light-emitting layer, which can effectively enhance the intramolecular dipole moment of the single host material, thereby accelerating the intramolecular exciton transfer and recombination, and ultimately significantly reducing the driving voltage of the OLED device, significantly enhancing the luminous efficiency, and extending the luminous lifetime.

[0323] Obviously, the above embodiments are merely examples for clear explanation, and are not intended to limit the implementation methods. For those skilled in the art, other different forms of changes or modifications can be made based on the above description. It is not necessary and impossible to list all the implementation methods here. The obvious changes or modifications derived from them are still within the protection scope of the invention.

Claims

1. An organic compound, characterized in that The organic compound has a structure shown in formula (1): In formula (1), Ring A is selected from a C6-C15 aromatic ring, a C3-C15 heteroaromatic ring; Ar 2 is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; L is selected from a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C3-C60 heteroarylene group; R 0 Selected from hydrogen, deuterium, amino, cyano, hydroxyl, thiol, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C1-C60 heteroalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; n1 is any integer selected from 0 to 5; When n1 is greater than or equal to 2, R 0 are the same or different, and each R 0 Can exist independently or in any adjacent R 0 They may be bonded to each other to form a substituted or unsubstituted C6-C60 aromatic ring, or a substituted or unsubstituted C3-C60 heteroaromatic ring; Ar is selected from the structure shown in formula A or formula B: In formula A or formula B, Z 1 -Z 14 Each is independently selected from CR or N; In formula A, Z 1 -Z 6 At least any two of them are selected from N; In formula B, Z 7 -Z 14 At least any two of them are selected from N; R is selected from hydrogen, deuterium, cyano, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C1-C60 heteroalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, Wherein, the substituents in the substituted C6-C60 arylene group, substituted C3-C60 heteroarylene group, substituted C1-C60 alkyl group, substituted C2-C60 alkenyl group, substituted C1-C60 heteroalkyl group, substituted C6-C60 aryl group, substituted C3-C60 heteroaryl group, substituted C6-C60 aromatic ring, substituted C3-C60 heteroaromatic ring are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl group, C3-C60 cycloalkyl group, C6-C60 aryl group, C3-C60 heteroaryl group, C6-C60 aromatic amine group, C3-C60 heteroaromatic amine group.

2. The organic compound according to claim 1, characterized in that Formula (1) is selected from any one of Formulas 1-1 to 1-3, wherein L, Ar, n1, R 0 ,Ar 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 any one of the structures of formula A-1, formula B-1 to formula B-3: In formula B-1 to formula B-3, n is selected from any integer from 0 to 5, R' is selected from hydrogen, deuterium, cyano, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C1-C60 heteroalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, and when n is greater than or equal to 2, R' is the same or different; In formula A-1, Ar 3 ,Ar 4 Each is independently selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group; Wherein, the substituents of the substituted C1-C60 alkyl, substituted C1-C60 heteroalkyl, substituted C6-C60 aryl and substituted C3-C60 heteroaryl are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amine and C3-C60 heteroaromatic amine.

4. The organic compound according to any one of claims 1 to 3, characterized in that The organic compound is selected from any one of the structures of Formula 1-A-1 to Formula 1-A-3 or Formula 1-B-1 to Formula 1-B-9, wherein L, n, n1, R 0 ,Ar 2 ,Ar 3 ,Ar 4 , R' is defined as in claim 3:

5. The organic compound according to any one of claims 1 to 4, characterized in that Ar 2 is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; Wherein, the substituents in the substituted C6-C30 aryl group and the substituted C3-C30 heteroaryl group are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine; Preferably, L is selected from substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene; Wherein, the substituent in the substituted C6-C30 arylene group and the substituted C3-C30 heteroarylene group is selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine; Preferably, R 0 Selected from hydrogen, deuterium, amino, cyano, hydroxyl, thiol, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; n1 is any integer selected from 0 to 5; When n1 is greater than or equal to 2, R 0 are the same or different, and each R 0 Can exist independently or in any adjacent R 0 They may be bonded to each other to form a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group; Wherein, the substituents in the substituted C1-C30 alkyl, substituted C2-C30 alkenyl, substituted C1-C30 heteroalkyl, substituted C6-C30 aryl, and substituted C3-C30 heteroaryl are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine; Preferably, in Formula 1-A-1 to Formula 1-A-3, Ar 3 ,Ar 4 Each is independently selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group; Wherein, the substituents in the substituted C6-C30 aryl group and the substituted C3-C30 heteroaryl group are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine; Preferably, in Formula 1-B-1 to Formula 1-B-9, n is selected from any integer from 0 to 5; R' is selected from hydrogen, deuterium, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and when n is greater than or equal to 2, R' is the same or different; Among them, the substituents of the substituted C1-C30 alkyl, substituted C1-C30 heteroalkyl, substituted C6-C30 aryl and substituted C3-C30 heteroaryl are selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amine and C3-C60 heteroaromatic amine.

6. The organic compound according to any one of claims 1 to 5, characterized in that Ar 2 is selected from substituted or unsubstituted A groups, wherein the A groups are selected from phenyl, naphthyl, phenanthryl, anthracenyl, fluoranthenyl, pyrenyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothienyl, dibenzothienyl, naphthobenzothienyl, carbazolyl, phenylcarbazolyl, benzocarbazolyl, benzophenylcarbazolyl, dibenzocarbazolyl, biphenylcarbazolyl, benzoxazolyl, naphthoxazolyl, phenanthroxazolyl, phenanthrobenzofuranyl, benzofuranobenzofuranyl, phenylcarbazolyl; Wherein, the substituent in the substituted A group is selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine; Preferably, the substituent in the substituted A group is selected from one or a combination of at least two of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexane, cyclopentane, phenyl, naphthyl, phenanthrenyl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracenyl, fluorenyl, pyrenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, carbazolyl, and benzocarbazolyl; Preferably, L is selected from substituted or unsubstituted B groups; The B group is selected from phenylene, naphthylene, phenanthrylene, binaphthylene, dibenzofuranylene, dibenzothiophenylene, benzonaphthofuranylene, benzonaphthothiophenylene; Wherein, the substituent in the substituted B group is selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine; Preferably, the substituent in the substituted B group is selected from one or a combination of at least two of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropyl, cyclohexyl, cyclopentyl, phenyl, naphthyl, phenanthryl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracenyl, fluorenyl, pyrenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, carbazolyl, and benzocarbazolyl; Preferably, n1 is selected from any integer between 0 and 5; R 0 is selected from hydrogen, deuterium, amino, cyano, hydroxyl, mercapto, a substituted or unsubstituted C group, wherein the C group is selected from methyl, ethyl, propyl, 1-butyl, 2-butyl, 3-butyl, adamantyl, cyclopropyl, cyclopentyl, cyclobutane, cyclohexyl, vinyl, propenyl, methoxy, methylthio, ethoxy, ethylthio, aldehyde, aminomethyl, methylamino, phenyl, naphthyl, phenanthryl, anthracenyl, fluoranthenyl, pyrenyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzodimethylfluorenyl, phenyl diphenylfluorenyl, benzospirobifluorenyl, furanyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, thienyl, benzothienyl, dibenzothienyl, naphthobenzothienyl, pyridyl, pyrrolyl, pyrimidinyl, oxazolyl, isoxazolyl, quinolyl, isoquinolyl, carbazolyl, phenylcarbazolyl, benzocarbazolyl, benzophenylcarbazolyl, dibenzocarbazolyl, biphenylcarbazolyl, benzoxazolyl, naphthoxazolyl, phenanthroxazolyl, phenanthrobenzofuranyl, benzofuranobenzofuranyl, phenylcarbazolyl; Wherein, the substituent of the substituted C group is selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine; Preferably, the substituent of the substituted C group is selected from one or a combination of at least two of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropyl, cyclohexyl, cyclopentyl, phenyl, naphthyl, phenanthrenyl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracenyl, fluorenyl, pyrenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, carbazolyl, benzocarbazolyl; When n1 is greater than or equal to 2, R 0 are the same or different, and each R 0 Can exist independently or in any adjacent R 0 They may be bonded to each other to form a substituted or unsubstituted A ring; The A ring is selected from a benzene ring, a naphthalene ring, a phenanthrene ring, an anthracene ring, a fluoranthene ring, a pyrene ring, a biphenyl ring, a terphenyl ring, a phenylnaphthalene ring, a naphthylbenzene ring, a triphenylene ring, a fluorene ring, a dimethylfluorene ring, a diphenylfluorene ring, a spirobifluorene ring, a benzodimethylfluorene ring, a benzodiphenylfluorene ring, a benzospirobifluorene ring, a benzofuran ring, a dibenzofuran ring, a naphthobenzofuran ring, a dinaphthofuran ring, a benzothiophene ring, a dibenzothiophene ring, a naphthobenzothiophene ring, a carbazole ring, a phenylcarbazole ring, a benzocarbazole ring, a benzophenylcarbazole ring, a dibenzocarbazole ring, a biphenylcarbazole ring, a benzoxazole ring, a naphthoxazole ring, a phenanthreneoxazole ring, a phenanthrenebenzofuran ring, a benzofuranbenzofuran ring, and a phenylcarbazolebenzofuran ring; Wherein, the substituent in the substituted A ring is selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amine, and C3-C60 heteroaromatic amine; Preferably, the substituent in the substituted A ring is selected from one or a combination of at least two of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexane, cyclopentane, phenyl, naphthyl, phenanthrenyl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracenyl, fluorenyl, pyrenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, carbazolyl, and benzocarbazolyl; Preferably, in Formula 1-A-1 to Formula 1-A-3, Ar 3 ,Ar 4 each independently selected from substituted or unsubstituted A groups; the A groups are selected from phenyl, naphthyl, phenanthryl, anthracenyl, fluoranthenyl, pyrenyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothienyl, dibenzothienyl, naphthobenzothienyl, carbazolyl, phenylcarbazolyl, benzocarbazolyl, benzophenylcarbazolyl, dibenzocarbazolyl, biphenylcarbazolyl, benzoxazolyl, naphthoxazolyl, phenanthroxazolyl, phenanthrobenzofuranyl, benzofuranobenzofuranyl, phenylcarbazolyl; Wherein, the substituent in the substituted A group is selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine; Preferably, the substituent in the substituted A group is selected from one or a combination of at least two of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexane, cyclopentane, phenyl, naphthyl, phenanthrenyl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracenyl, fluorenyl, pyrenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, carbazolyl, and benzocarbazolyl; Preferably, in Formula 1-B-1 to Formula 1-B-9, n is selected from any integer of 0-5, R' is selected from hydrogen, deuterium, cyano, substituted or unsubstituted D groups, and when n is greater than or equal to 2, R' is the same or different; D groups are selected from methyl, ethyl, propyl, primary butyl, secondary butyl, tert-butyl, adamantyl, cyclopropyl, cyclopentyl, cyclobutane, cyclohexyl, methoxy, methylthio, ethoxy, ethylthio, aldehyde, aminomethyl, methylamino, phenyl, naphthyl, phenanthryl, anthracenyl, fluoranthenyl, pyrenyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzodimethylfluorenyl , benzodiphenylfluorenyl, benzospirobifluorenyl, furanyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, thienyl, benzothienyl, dibenzothienyl, naphthobenzothienyl, pyridyl, pyrrolyl, pyrimidinyl, oxazolyl, isoxazolyl, quinolyl, isoquinolyl, carbazolyl, phenylcarbazolyl, benzocarbazolyl, benzophenylcarbazolyl, dibenzocarbazolyl, biphenylcarbazolyl, benzoxazolyl, naphthoxazolyl, phenanthroxazolyl, phenanthrobenzofuranyl, benzofuranobenzofuranyl, phenylcarbazolyl; Wherein, the substituent of the substituted D group is selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine; Preferably, the substituent of the substituted D group is selected from one or a combination of at least two of deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexane, cyclopentane, phenyl, naphthyl, phenanthrenyl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracenyl, fluorenyl, pyrenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, carbazolyl, and benzocarbazolyl.

7. The organic compound according to any one of claims 1 to 6, characterized in that The compound is selected from the following structures:

8. An organic electroluminescent material, characterized in that: The organic electroluminescent material comprises the organic compound according to any one of claims 1 to 7.

9. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises an anode, a cathode and an organic layer between the anode and the cathode, wherein the organic layer comprises the organic compound according to any one of claims 1 to 7 or the organic electroluminescent material according to claim 8; Preferably, the organic layer includes any one or a combination of at least two of 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; Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the organic compound according to any one of claims 1 to 7 or the organic electroluminescent material according to claim 8.

10. An electronic device, characterized in that: The electronic device comprises the organic electroluminescent device according to any one of claims 9 or the organic electroluminescent material according to claim 8 or the organic compound according to any one of claims 1-7.

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