Organic electroluminescent compound and use thereof

Abstract

The application belongs to the technical field of display, and particularly relates to an organic electroluminescent compound and application thereof. The organic electroluminescent compound provided by the application has a structure of formula (1), and the application of the organic electroluminescent compound provided by the application in an organic electroluminescent device can reduce the driving voltage of the organic electroluminescent device, improve the current efficiency and prolong the service life.

Description

Technical Field

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

[0002] Organic light-emitting diodes (OLEDs) are semiconductor devices that achieve photoelectric conversion based on a charge injection excitation mechanism. Their typical structure consists of an anode, a cathode, and a sandwich functional system: the anode is a metal oxide layer with hole transport characteristics, the cathode is a low work function metal material, and the sandwich functional layer system usually consists of a carrier injection layer, a transport layer, an exciton confinement layer, and a bipolar light-emitting dielectric layer.

[0003] In operation, holes migrate to the luminescent region through the hole injection layer, while electrons are transported to the region through the electron injection layer. When these two types of charge carriers recombine in the luminescent medium, they form excitons in an excited state. These excited excitons release energy through radiative transitions, and their energy conversion efficiency directly determines the luminescent performance of the device.

[0004] The choice of material system is a core factor affecting device performance. An ideal light-emitting material needs to possess high stability, an energy level structure that matches adjacent functional layers, and balanced carrier mobility characteristics. However, the performance of existing organic electroluminescent materials is poor, resulting in high device driving voltage, low current efficiency, and short operating lifetime. These technical bottlenecks severely restrict the industrial application of OLEDs. Summary of the Invention

[0005] The purpose of this invention is to overcome the problems of poor performance of existing organic electroluminescent materials, which lead to high driving voltage, low current efficiency and short device life, and to provide an organic electroluminescent compound and its application.

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

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

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

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

[0010] In this invention, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have substituents (hereinafter, for ease of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an unsubstituted aryl group. The aforementioned substituent, i.e., Rc, can be, for example, deuterium, halogen, cyano, C1-C30 alkyl, C6-C30 aryl, or C1-C30 heteroaryl. Optionally, it can be, for example, deuterium, a halogen group, cyano, alkyl, haloalkyl, trialkylsilyl, deuterated alkyl, aryl, heteroaryl, etc. Of course, the number of substituents Rc can be one or more. When two substituents Rc are attached to the same atom, these 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 two adjacent substituents Rc can exist independently or fuse with the functional group to which they are attached to form a ring.

[0011] In this invention, C1-C30, C3-C30, and C6-C30 define the range of carbon atoms, and the number of carbon atoms is any integer within the defined range. For example, C6-C30 aryl means that the number of carbon atoms representing the aryl group can be any integer within the range of 6-30, such as 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, and 30.

[0012] In this invention, the term "alkyl" refers, whether as part of other terms or used alone, to a saturated hydrocarbon group, which may be straight-chain or branched. The term "C1-C30 alkyl" is derived from a monovalent substituent of a straight-chain or branched saturated hydrocarbon having 1 to 30 carbon atoms, preferably 1 to 25 carbon atoms, and more preferably 1 to 20 carbon atoms. Examples of such substituents include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.

[0013] In this invention, the terms "aryl" and "arylene" include monocyclic, polycyclic, or fused-ring aryl groups, wherein the rings may be interrupted by short non-aromatic units, and may contain a spirostructure. Aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, fluorene, and spirodifluorene. Arylene groups include, but are not limited to, phenylene, biphenylene, terphenylene, naphthylene, phenanthrylene, anthraceneene, fluorene, and spirodifluorene. Arylene refers to a divalent or polyvalent group formed by the further loss of one or more hydrogen atoms from an aryl group.

[0014] In this invention, the terms "heteroaryl" and "hybrid heteroaryl" include monocyclic, polycyclic, or fused-ring heteroaryl groups, wherein the rings may be interrupted by short non-aromatic units, and the heteroatoms include nitrogen, oxygen, sulfur, and selenium. Heteroaryl groups in this invention include, but are not limited to, furanyl, phenylthio, pyrroleyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetraazinyl, triazolyl, tetrazolyl, pyridinyl, and others. Pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiopheneyl, isobenzofuranyl, dibenzofuranyl, dibenzothiopheneyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisooxazolyl, benzooxazolyl, isoindolyl, indolyl, indazoleyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxalinyl, carbazoleyl, phenoxazinyl, phenthiazinyl, phenanthidyl, benzom-dioxacyclopentenyl, Dihydroacridinyl and its derivatives, etc.; heteroaryl groups include, but are not limited to, imidinyl, phenylthioyl, pyrrolyl, imidazolyl, pyrazolyl, imidazolyl, imidazithiazolyl, isothiazolyl, isoxazolyl, imidazithiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridinyl, pyridazinyl, benzofuranyl, benzothiopheneyl, isobenzofuranyl, dibenzofuranyl Furanyl, dibenzothiophene, benzimidazolyl, benzithiazolyl, benzisisothiazolyl, benzisisooxazolyl, benzisoxazolyl, isoindolyl, indolyl, indazolyl, benzisthiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxolinyl, carbazolyl, phenoxazinyl, phenthiazinyl, phenanthridineyl, benzism-dioxacyclopentenyl, dihydroacridylyl, and their derivatives, etc.

[0015] In this invention, the term "single bond" refers to the connection between two adjacent groups.

[0016] In this invention, unless otherwise specified, the substituents do not fuse with the group to which they belong.

[0017] In this invention, if the group is not specified as substituted or unsubstituted, it means that it has not been substituted.

[0018] In this invention, It refers to the chemical bond that connects with other groups.

[0019] In this invention, the non-positioning connecting key involves a single bond extending from the ring system. "This means that one end of the linking 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."

[0020] The solution adopted in this invention is as follows: This invention provides an organic electroluminescent compound having the structure shown in formula (1):

[0021] In formula (1), Ra and Rb are selected from the structure shown in formula (1-1) and the other is selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl. R 1 Selected from hydrogen or deuterium; n1 is an integer selected from 0 to 4;

[0022] In equation (1-1), L 1 and L 2 Each is independently selected from single-bonded, substituted, or unsubstituted C6-C30 arylene groups; R 2 and R 3 Each is independently selected from hydrogen or deuterium; n2 is selected from integers between 0 and 6; n3 is selected from integers from 0 to 9; The substituted C6-C30 aryl, substituted C3-C30 heteroaryl, and substituted C6-C30 arylene are each independently substituted by at least one of the following groups: deuterium, halogen, cyano, C1-C18 alkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0023] Optional, X is selected from O; Optional, X is selected from S; Optionally, n1 is selected from 0, 1, 2, 3, 4; Optionally, n2 is selected from 0, 1, 2, 3, 4, 5, 6; Optionally, n3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9; Preferably, when L 1 and L 2 When it is a single bond, Ra or Rb is neither a substituted nor an unsubstituted phenanthroline group.

[0024] Preferably, the organic electroluminescent compound has the structure shown in formulas (2) to (3): In the formula, Ra and Rb are each independently selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups; R 1 R 2 R 3 n1, n2, n3, L 1 L 2The definition is as described above.

[0025] Preferably, the organic electroluminescent compound has the structure shown in formulas (4) to (13);

[0026] .

[0027] In the formula, Ra and Rb are each independently selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups; R 1 R 2 R 3 n1, n2, n3, L 1 L 2 The definition is as described above.

[0028] Preferably, L 1 Selected from single-bonded, substituted or unsubstituted C6-C18 arylene groups; Wherein, the substituted C6-C18 arylene is substituted by at least one selected from the group consisting of: deuterium, halogen, cyano, C1-C12 alkyl, C6-C18 aryl; Preferably, L 1 Selected from single-bonded, substituted or unsubstituted C6-C12 arylene groups; Wherein, the substituted C6-C12 arylene is substituted by at least one selected from the group consisting of: deuterium, halogen, cyano, C1-C6 alkyl, C6-C12 aryl; Preferably, L 1 The group D is selected from single-bonded, substituted, or unsubstituted groups, wherein the group D is selected from the group consisting of:

[0029]

[0030]

[0031] ; Wherein, the substituted group D is substituted by at least one selected from the group consisting of: deuterium, tert-butyl, cyano, phenyl, naphthyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, and binaphthyl.

[0032] Preferably, L 2 Selected from single-bonded, substituted or unsubstituted C6-C18 arylene groups; Wherein, the substituted C6-C18 arylene is substituted by at least one selected from the group consisting of: deuterium, halogen, cyano, C1-C12 alkyl, C6-C18 aryl; Preferably, L 2 Selected from single-bonded, substituted or unsubstituted C6-C12 arylene groups; Wherein, the substituted C6-C12 arylene is substituted by at least one selected from the group consisting of: deuterium, halogen, cyano, C1-C6 alkyl, C6-C12 aryl; Preferably, L 2 The group F is selected from single-bonded, substituted, or unsubstituted groups, wherein the group F is selected from the group consisting of:

[0033]

[0034]

[0035] ; Wherein, the substituted group F is substituted by at least one selected from the group consisting of: deuterium, tert-butyl, cyano, phenyl, naphthyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, and binaphthyl.

[0036] Preferably, Ra is selected from substituted or unsubstituted C6-C18 aryl groups and substituted or unsubstituted C3-C18 heteroaryl groups; Wherein, the substituted C6-C18 aryl and the substituted C3-C18 heteroaryl are substituted by at least one of the following groups: deuterium, halogen, cyano, C1-C12 alkyl, C6-C18 aryl, C3-C18 heteroaryl; Preferably, Ra is selected from substituted or unsubstituted C6-C12 aryl groups and substituted or unsubstituted C3-C12 heteroaryl groups; Wherein, the substituted C6-C12 aryl and the substituted C3-C12 heteroaryl are substituted by at least one of the following groups: deuterium, halogen, cyano, C1-C6 alkyl, C6-C12 aryl, C3-C12 heteroaryl; Preferably, Ra is selected from substituted or unsubstituted group E, said group E being selected from the group consisting of:

[0037]

[0038]

[0039] ; Wherein, the substituted group E is substituted by at least one selected from the group consisting of: deuterium, halogen, cyano, tert-butyl, phenyl, naphthyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, binaphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, dibenzofuranyl, dibenzothiophene.

[0040] Preferably, Rb is selected from substituted or unsubstituted C6-C18 aryl groups and substituted or unsubstituted C3-C18 heteroaryl groups; Wherein, the substituted C6-C18 aryl and the substituted C3-C18 heteroaryl are substituted by at least one of the following groups: deuterium, halogen, cyano, C1-C12 alkyl, C6-C18 aryl, C3-C18 heteroaryl; Preferably, Rb is selected from substituted or unsubstituted C6-C12 aryl groups and substituted or unsubstituted C3-C12 heteroaryl groups; Wherein, the substituted C6-C12 aryl and the substituted C3-C12 heteroaryl are substituted by at least one of the following groups: deuterium, halogen, cyano, C1-C6 alkyl, C6-C12 aryl, C3-C12 heteroaryl; Preferably, Rb is selected from substituted or unsubstituted groups G, wherein the groups G are selected from the group consisting of:

[0041]

[0042]

[0043] ; Wherein, the substituted group G is substituted by at least one selected from the group consisting of: deuterium, halogen, cyano, tert-butyl, phenyl, naphthyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, binaphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, dibenzofuranyl, dibenzothiophene.

[0044] It is understandable that in this invention, Indicates the connection location.

[0045] It is understood that the number of substituents is not limited in this invention, and the number of substituents can be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, etc. For example, when the substituent is deuterium, it can be fully deuterated, semi-deuterated, or 1, 2, 3, 4... deuterium substitutions.

[0046] Preferably, the organic electroluminescent compound is selected from one of the following structures:

[0047]

[0048] .

[0049] This invention also provides a method for synthesizing the compound shown, the specific synthetic route of which is shown in the following reaction formula: Synthesis of the structure shown in equation (2):

[0050] Synthesis of the structure shown in equation (3):

[0051] Or:

[0052] The present invention also provides a charge-generating material, which includes any one or a combination of at least two of the organic electroluminescent compounds described above.

[0053] Preferably, the charge-generating material comprises an n-type charge-generating material, which includes any one or a combination of at least two of the organic electroluminescent compounds described above.

[0054] The present invention also provides an organic electroluminescent device, the organic electroluminescent device comprising: a cathode; an anode disposed opposite to the cathode; and at least two light-emitting units disposed between the cathode and the anode; wherein, Between two adjacent light-emitting units there is a charge-generating layer, which includes the structure shown in equation (1):

[0055] Equation (1) In formula (1), Ra and Rb are selected from the structure shown in formula (1-1) and the other is selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl. R 1 Selected from hydrogen or deuterium; n1 is an integer selected from 0 to 4;

[0056] Equation (1-1) In equation (1-1), L 1 and L 2 Each is independently selected from single-bonded, substituted, or unsubstituted C6-C30 arylene groups; R 2 and R 3Each is independently selected from hydrogen or deuterium; n2 is selected from integers between 0 and 6; n3 is selected from integers from 0 to 9; The substituted C6-C30 aryl, substituted C3-C30 heteroaryl, and substituted C6-C30 arylene are each independently substituted by at least one of the following groups: deuterium, halogen, cyano, C1-C18 alkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0057] Optional, X is selected from O; Optional, X is selected from S; Optionally, n1 is selected from 0, 1, 2, 3, 4; Optionally, n2 is selected from 0, 1, 2, 3, 4, 5, 6; Optionally, n3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9; Preferably, the organic electroluminescent compound has the structure shown in formulas (2) to (3): In the formula, Ra and Rb are each independently selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups; R 1 R 2 R 3 n1, n2, n3, L 1 L 2 The definition is as described above.

[0058] Preferably, the organic electroluminescent compound has the structure shown in formulas (4) to (13):

[0059] .

[0060] In the formula, Ra and Rb are each independently selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups; R 1 R 2 R 3 n1, n2, n3, L 1 L 2 The definition is as described above.

[0061] Preferred, L 1 Selected from single-bonded, substituted or unsubstituted C6-C18 arylene groups; Wherein, the substituted C6-C18 arylene is substituted by at least one selected from the group consisting of: deuterium, halogen, cyano, C1-C12 alkyl, C6-C18 aryl; Preferred, L 1 Selected from single-bonded, substituted or unsubstituted C6-C12 arylene groups; Wherein, the substituted C6-C12 arylene is substituted by at least one selected from the group consisting of: deuterium, halogen, cyano, C1-C6 alkyl, C6-C12 aryl; Preferred, L 1 The group D is selected from single-bonded, substituted, or unsubstituted groups, wherein the group D is selected from the group consisting of:

[0062]

[0063]

[0064] ; Wherein, the substituted group D is substituted by at least one selected from the group consisting of: deuterium, tert-butyl, cyano, phenyl, naphthyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, and binaphthyl.

[0065] Preferred, L 2 Selected from single-bonded, substituted or unsubstituted C6-C18 arylene groups; Wherein, the substituted C6-C18 arylene is substituted by at least one selected from the group consisting of: deuterium, halogen, cyano, C1-C12 alkyl, C6-C18 aryl; Preferred, L 2 Selected from single-bonded, substituted or unsubstituted C6-C12 arylene groups; Wherein, the substituted C6-C12 arylene is substituted by at least one selected from the group consisting of: deuterium, halogen, cyano, C1-C6 alkyl, C6-C12 aryl; Preferred, L 2 The group F is selected from single-bonded, substituted, or unsubstituted groups, wherein the group F is selected from the group consisting of:

[0066]

[0067]

[0068] ; Wherein, the substituted group F is substituted by at least one selected from the group consisting of: deuterium, tert-butyl, cyano, phenyl, naphthyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, and binaphthyl.

[0069] Preferably, Ra is selected from substituted or unsubstituted C6-C18 aryl groups and substituted or unsubstituted C3-C18 heteroaryl groups; Wherein, the substituted C6-C18 aryl and the substituted C3-C18 heteroaryl are substituted by at least one of the following groups: deuterium, halogen, cyano, C1-C12 alkyl, C6-C18 aryl, C3-C18 heteroaryl; Preferably, Ra is selected from substituted or unsubstituted C6-C12 aryl groups and substituted or unsubstituted C3-C12 heteroaryl groups; Wherein, the substituted C6-C12 aryl and the substituted C3-C12 heteroaryl are substituted by at least one of the following groups: deuterium, halogen, cyano, C1-C6 alkyl, C6-C12 aryl, C3-C12 heteroaryl; Preferably, Ra is selected from substituted or unsubstituted group E, said group E being selected from the group consisting of:

[0070]

[0071]

[0072] ; Wherein, the substituted group E is substituted by at least one selected from the group consisting of: deuterium, halogen, cyano, tert-butyl, phenyl, naphthyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, binaphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, dibenzofuranyl, dibenzothiophene.

[0073] Preferably, Rb is selected from substituted or unsubstituted C6-C18 aryl groups and substituted or unsubstituted C3-C18 heteroaryl groups; Wherein, the substituted C6-C18 aryl and the substituted C3-C18 heteroaryl are substituted by at least one of the following groups: deuterium, halogen, cyano, C1-C12 alkyl, C6-C18 aryl, C3-C18 heteroaryl; Preferably, Rb is selected from substituted or unsubstituted C6-C12 aryl groups and substituted or unsubstituted C3-C12 heteroaryl groups; Wherein, the substituted C6-C12 aryl and the substituted C3-C12 heteroaryl are substituted by at least one of the following groups: deuterium, halogen, cyano, C1-C6 alkyl, C6-C12 aryl, C3-C12 heteroaryl; Preferably, Rb is selected from substituted or unsubstituted groups G, wherein the groups G are selected from the group consisting of:

[0074]

[0075]

[0076] ; Wherein, the substituted group G is substituted by at least one selected from the group consisting of: deuterium, halogen, cyano, tert-butyl, phenyl, naphthyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, binaphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, dibenzofuranyl, dibenzothiophene.

[0077] It is understandable that in this invention, Indicates the connection location.

[0078] It is understood that the number of substituents is not limited in this invention, and the number of substituents can be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, etc. For example, when the substituent is deuterium, it can be fully deuterated, semi-deuterated, or 1, 2, 3, 4... deuterium substitutions.

[0079] Preferably, the organic electroluminescent compound is selected from one of the following structures:

[0080]

[0081] .

[0082] Preferably, the charge-generating layer comprises the charge-generating material as described above or the organic electroluminescent compound as described above.

[0083] Preferably, the charge generation layer comprises an n-type charge generation layer and a p-type charge generation layer, wherein the n-type charge generation layer comprises the organic electroluminescent compound as described above.

[0084] Preferably, the n-type charge generation layer further comprises a metal dopant; the metal dopant is one or a combination of at least two of alkali metals, alkaline earth metals and rare earth metals, or a combination of at least two of metal alloys containing alkali metals, alkaline earth metals and rare earth metals.

[0085] Preferably, the metal dopant is selected from Li, Mg, or Yb, or any combination thereof.

[0086] Preferably, the p-type charge generation layer is not subject to any special restrictions and can be set in a conventional manner in the art and matched with the above-mentioned n-type charge generation layer.

[0087] More preferably, the p-type charge generation layer may be composed of HAT-CN and TCTA, and the present invention does not make any special setting on their ratio.

[0088] Preferably, the organic electroluminescent device includes a first light-emitting unit and a second light-emitting unit, the first light-emitting unit being disposed near the anode, the second light-emitting unit being disposed near the cathode, and the charge-generating layer being disposed between the first light-emitting unit and the second light-emitting unit; Preferably, the organic electroluminescent device includes an anode, a hole injection layer, a first hole transport layer, a first electron blocking layer, a first light-emitting unit, a first hole blocking layer, a first electron transport layer, an n-type charge generation layer, a p-type charge generation layer, a second hole transport layer, a second electron blocking layer, a second light-emitting unit, a second hole blocking layer, a second electron transport layer, an electron injection layer, and a cathode, all stacked together.

[0089] Preferably, the first light-emitting unit or the second light-emitting unit includes a blue light-emitting layer, a red light-emitting layer, or a green light-emitting layer; Preferably, the first light-emitting unit or the second light-emitting unit includes a blue light-emitting layer.

[0090] Preferably, the blue light-emitting layer comprises a compound with the following structure:

[0091] Preferably, the anode comprises an anode material, preferably a material with a large work function that facilitates hole injection into the first hole transport layer. For example, the anode material may include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but is not limited thereto.

[0092] More preferably, the anode is selected as indium tin oxide (ITO).

[0093] Preferably, the hole injection layer is used to enhance the ability to inject holes into the first hole transport layer. The hole injection layer can be selected from benzidine derivatives, starburst-like aryl amine compounds, phthalocyanine derivatives, or other materials; the present invention does not impose any special limitations on this. The material of the hole injection layer can, for example, be selected from the following compounds or any combination thereof:

[0094]

[0095]

[0096] .

[0097] Preferably, the first hole transport layer or the second hole transport layer comprises a compound selected from the following compounds or any combination thereof:

[0098]

[0099] .

[0100] Preferably, the first electron blocking layer or the second electron blocking layer comprises the following structure:

[0101] Preferably, the first hole-blocking layer or the second hole-blocking layer comprises the following structure:

[0102] Preferably, the first electron transport layer or the second electron transport layer is composed of 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBI) and lithium octahydroxyquinoline (LiQ).

[0103]

[0104] Preferably, the electron injection layer is used to enhance the ability to inject electrons into the second electron transport layer. The electron injection layer may include inorganic materials such as alkali metal sulfides and alkali metals, or may include complexes of alkali metals and organic materials. More preferably, the electron injection layer may include ytterbium (Yb).

[0105] Preferably, the cathode may comprise a cathode material that has a small work function and facilitates electron injection into the functional layers. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca.

[0106] It should be noted that the above-mentioned organic electroluminescent devices are fabricated using conventional methods in the art, such as depositing layers on a substrate.

[0107] The present invention also provides an application of the above-described organic electroluminescent compound, or the above-described n-type charge generating layer, or the above-described organic electroluminescent device in optical fiber equipment, lighting equipment, electrophotographic photosensitive equipment, photoelectric converters, organic solar cells, switching element equipment, organic light-emitting field-effect transistors, image sensors, or dye lasers.

[0108] The present invention also provides an organic electroluminescent product, which includes the above-described organic electroluminescent device.

[0109] The present invention also provides an electronic device comprising the above-described organic electroluminescent compound.

[0110] Preferably, the electronic devices include perovskite photovoltaic devices, perovskite light-emitting devices, display devices, organic integrated circuits, organic field-effect transistors, organic thin-film transistors, organic light-emitting transistors, organic solar cells, organic photodetectors, organic photoreceptors, organic field quenching devices, luminescent electrochemical cells, and organic laser diodes.

[0111] The above can be combined freely.

[0112] The beneficial effects of this invention are: The organic electroluminescent compound provided by this invention has the structure of formula (1), in which a naphthalene ring is used for bridging in the core, which can improve the thermal stability of the material and avoid molecular crystallization; at the same time, it can regulate the molecular energy level, balance the carrier transport process, and suppress concentration quenching and exciton annihilation. The structure of formula (1) can also promote the formation of stable amorphous thin films and extend the service life of the device. In summary, applying the organic electroluminescent compound provided by this invention to organic electroluminescent devices can reduce the driving voltage, improve the current efficiency, and extend the service life of organic electroluminescent devices. Attached Figure Description To more clearly illustrate the specific embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the specific embodiments or the prior art will be briefly introduced below. Obviously, the drawings described below are some embodiments of the present invention. For those skilled in the art, other drawings can be obtained from these drawings without creative effort.

[0113] Figure 1 This is a structural diagram of the stacked organic electroluminescent device in the device embodiment of the present invention; 1-Anode, 2-Hole injection layer, 3-First hole transport layer, 4-First electron blocking layer, 5-First organic light-emitting layer, 6-First hole blocking layer, 7-First electron transport layer, 8-n-type charge generation layer, 9-p-type charge generation layer, 10-Second hole transport layer, 11-Second electron blocking layer, 12-Second organic light-emitting layer, 13-Second hole blocking layer, 14-Second electron transport layer, 15-Electron injection layer, 16-Cathode. Detailed Implementation

[0114] The following embodiments are provided to better understand the present invention and are not limited to the preferred embodiments described. They do not constitute a limitation on the content and scope of protection of the present invention. Any product that is the same as or similar to the present invention, derived by any person under the guidance of the present invention or by combining the features of the present invention with other prior art, falls within the protection scope of the present invention.

[0115] For experiments not specifically described in the examples, the procedures or conditions should be followed according to the conventional experimental procedures described in the literature in this field. Reagents or instruments whose manufacturers are not specified are all commercially available conventional reagent products.

[0116] When referring to material ratios, unless otherwise specified, the ratio refers to the volume ratio.

[0117] Synthesis of intermediate C1-A:

[0118] In a 2-liter three-necked flask, under nitrogen protection, add starter C1-a (248.06 mmol), starter C1-b (248.06 mmol), potassium carbonate (620.15 mmol), dioxane (440 mL), water (110 mL), tetraphenylphosphine palladium (2.481 mmol), and 90 mL of other ingredients. The reaction was carried out at C for 12 hours. After the reaction was completed, the product was extracted with dichloromethane, the organic phase was dried with anhydrous sodium sulfate to remove the organic solvent, ethanol was added and stirred for 1 hour, and the product Cl-A-1 was obtained by filtration (yield 89.61%).

[0119] In a 1-liter three-necked flask, under nitrogen protection, intermediate C1-A-1 (210.00 mmol), bis-pinacol borate (315.00 mmol), anhydrous dioxane (600 mL), 1,1'-bisdiphenylphosphine ferrocene palladium dichloride (2.1 mmol), potassium acetate (525.00 mmol), and 105 The reaction was carried out at C for 12 h. After the reaction was completed, water was added to quench the reaction, and the product was extracted with dichloromethane. The organic layer was dried with anhydrous magnesium sulfate to remove the organic solvent. The crude product was passed through a fast column with a mixed solvent (dichloromethane: tetrahydrofuran = 1:1), and n-hexane was added to slurry to obtain intermediate C1-A (yield 88.8%).

[0120] Intermediate C14-A was synthesized using the same method as intermediate C1-A, and the synthetic route is shown below:

[0121] Intermediate C14-A was obtained in 87.3% yield.

[0122] Synthesis of intermediate C25-B:

[0123] In a 2-liter three-necked flask, under nitrogen protection, add raw material C25-c (300.00 mmol), raw material C25-d (300.00 mmol), tetrahydrofuran (800 ml), sodium metabisulfite (360.00 mmol), and 70 ml of other ingredients. The reaction was carried out at C for 12 h. After the reaction was completed, water was added to quench the reaction, and the product was extracted with dichloromethane. The organic layer was dried with anhydrous magnesium sulfate to remove the organic solvent. The crude product was filtered through a column in a mixed solvent (dichloromethane: n-hexane = 1: 3) to give intermediate C25-B (yield 80.4%).

[0124] Intermediate Cn-B was synthesized using the same method as intermediate C25-B, with the difference being the substitution of the relevant raw materials. The specific structures of the raw materials and intermediate Cn-B are shown in Table 1.

[0125] Table 1 Intermediate Cn-B and raw materials for synthesis

[0126] Synthesis Example 1 This embodiment provides a method for synthesizing compound C-1, and the synthetic route is shown in the following reaction formula:

[0127] In a 250 mL three-necked flask, under nitrogen protection, add starting material C1-A (28.00 mmol), intermediate C1-B (28.00 mmol), dioxane:water = 4:1 (160 mL: 40 mL), [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (0.140 mmol), potassium carbonate (70.00 mmol), and 95... The reaction was carried out at C for 12 hours. After the reaction was completed, sufficient water was added to quench the reaction. The crude product solid was obtained by filtration. The solid was subjected to rapid column chromatography with chlorobenzene. The solvent was removed and crystallized from the column chromatography solution. The product C-1 was purified by recrystallization of o-dichlorobenzene (yield 68.8%).

[0128] Elemental analysis: C 43 H 28 N2, theoretical value: C, 90.18; H, 4.93; N, 4.89; measured value: C, 90.19; H, 4.94; N, 4.87; HRMS (ESI) m / z (M+): theoretical value: 572.23, measured value: 573.12.

[0129] Synthesis Example 2 This embodiment provides a method for synthesizing compound C-9, and the synthetic route is shown in the following reaction formula:

[0130] In a 500 mL three-necked flask, C1 (18.00 mmol), trifluoromethanesulfonic acid (48.00 mmol), and deuterium benzene (200 mL) were added, and the mixture was refluxed for 36 hours. After the reaction was complete, the organic solvent was evaporated, and the crude product was purified by column chromatography (dichloromethane:n-hexane = 3:1) to give compound C-9 (yield 85.2%).

[0131] Elemental analysis: C 43 D 28 N2. Theoretical values: C, 85.95; H, 9.39; N, 4.66; Measured values: C, 85.97; H, 9.38; N, 4.65; HRMS (ESI) m / z [M+H]+: Theoretical value: 600.40, Measured value: 601.28.

[0132] Synthesis Example 3 Compound C-14 was synthesized using the synthetic method of Example 1, except that starting material C14-A was used instead of starting material C1-A, and starting material C14-B was used instead of starting material C1-B. The synthetic route is shown below:

[0133] Compound C-14 was obtained in 76.6% yield. Elemental analysis: C 42 H 27 N3, theoretical values: C, 87.93; H, 4.74; N, 7.32; measured values: C, 87.96; H, 4.72; N, 7.31; HRMS (ESI) m / z (M+): theoretical value: 573.22, measured value: 574.20.

[0134] Synthesis Example 4 Compound C-17 was synthesized using the synthetic method of Example 1, except that starting material C14-A was used instead of starting material C1-A, and starting material C17-B was used instead of starting material C1-B. The synthetic route is shown below:

[0135] Compound C-17 was obtained in 74.5% yield. Elemental analysis: C 46 H 29 N3, theoretical value: C, 88.58; H, 4.69; N, 6.74; measured value: C, 88.59; H, 4.70; N, 6.72; HRMS (ESI) m / z (M+): theoretical value: 623.24, measured value: 624.18.

[0136] Synthesis Example 5 This embodiment provides a method for synthesizing compound C-21, and the synthetic route is shown in the following reaction formula:

[0137] In a 250 mL three-necked flask, under nitrogen protection, add starting material C21-B (28.00 mmol), intermediate C1-A-1 (28.00 mmol), toluene (200 mL), tris(dibenzylacetone)dipalladium (0.140 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.280 mmol), sodium tert-butoxide (70.00 mmol), and 110 mL of other reagents. The reaction was carried out at C for 12 hours. After the reaction was completed, sufficient water was added to quench the reaction, followed by extraction with dichloromethane, passing through a fast column, and then recrystallizing the concentrated chlorobenzene twice to obtain product C-21 (yield 78.8%).

[0138] Elemental analysis: C 37 H 24N2, theoretical value: C, 89.49; H, 4.87; N, 5.64; measured value: C, 89.51; H, 4.88; N, 5.61; HRMS (ESI) m / z (M+): theoretical value: 496.19, measured value: 497.12.

[0139] Synthesis Example 6 Compound C-25 was synthesized using the synthetic method of Example 1, except that starting material C1-a was used instead of starting material C1-A, and starting material C25-B was used instead of starting material C1-B. The synthetic route is shown below:

[0140] Compound C-25 was obtained in 77.6% yield. Elemental analysis: C 41 H 26 N2, theoretical values: C, 90.08; H, 4.79; N, 5.12; measured values: C, 90.10; H, 4.78; N, 5.11; HRMS (ESI) m / z (M+): theoretical value: 546.21, measured value: 547.28.

[0141] Synthesis Example 7 Compound C-31 was synthesized using the synthetic method of Example 5, except that starting material C1-A-1 was replaced with starting material C14-A-1. The synthetic route is shown below:

[0142] Compound C-31 was obtained in 68.7% yield. Elemental analysis: C 37 H 24 N2, theoretical value: C, 89.49; H, 4.87; N, 5.64; measured value: C, 89.52; H, 4.86; N, 5.62; HRMS (ESI) m / z (M+): theoretical value: 496.19, measured value: 497.12.

[0143] Synthesis Example 8 Compound C-33 was synthesized using the same method as in Example 1, except that starting material C14-a was used instead of starting material C1-A, and starting material C33-B was used instead of starting material C1-B. The synthetic route is shown in the following reaction formula:

[0144] Compound C-33 was obtained in 78.8% yield. Elemental analysis: C 36 H 23N3, theoretical values: C, 86.90; H, 4.66; N, 8.44; measured values: C, 86.92; H, 4.65; N, 8.43; HRMS (ESI) m / z (M+): theoretical value: 497.19, measured value: 498.13.

[0145] Synthesis Example 9 Compound C-41 was synthesized using the same method as in Example 1, except that starting material C41-B was used instead of starting material C1-B. The synthetic route is shown below: Compound C-41 was obtained in 76.6% yield. Elemental analysis: C 43 H 28 N2, theoretical values: C, 90.18; H, 4.93; N, 4.89; measured values: C, 90.19; H, 4.94; N, 4.87; HRMS (ESI) m / z (M+): theoretical value: 572.23, measured value: 573.15.

[0146] Synthesis Example 10 Compound C-45 was synthesized using the same method as in Example 1, except that starting material C1-B was replaced with starting material C45-B. The synthetic route is shown below:

[0147] Compound C-45 was obtained in 78.3% yield. Elemental analysis: C 47 H 30 N2, theoretical values: C, 90.65; H, 4.86; N, 4.50; measured values: C, 90.66; H, 4.89; N, 4.46; HRMS (ESI) m / z (M+): theoretical value: 622.24, measured value: 623.21.

[0148] Synthesis Example 11 This embodiment provides a method for synthesizing compound C-49, and the synthetic route is shown in the following reaction formula:

[0149] In a 500 mL three-necked flask, C-41 (18.00 mmol), trifluoromethanesulfonic acid (36.00 mmol), and deuterium benzene (100 mL) were added, and the mixture was refluxed for 36 hours. After the reaction was complete, the organic solvent was evaporated, and the crude product was purified by column chromatography (dichloromethane:n-hexane = 3:1) to give compound C-49 (yield 89.8%).

[0150] Elemental analysis: C 43 D 28 N2. Theoretical values: C, 85.95; H, 9.39; N, 4.66; Measured values: C, 85.96; H, 9.40; N, 4.64; HRMS (ESI) m / z [M+H]+: Theoretical value: 600.40, Measured value: 601.24.

[0151] Synthesis Example 12 Compound C-51 was synthesized using the same method as in Example 1, except that starting material C14-A was used instead of starting material C1-A, and starting material C41-B was used instead of starting material C1-B. The synthetic route is shown below:

[0152] Intermediate C-51 was obtained with a yield of 88.6%. Elemental analysis: C 43 H 28 N2, theoretical values: C, 90.18; H, 4.93; N, 4.89; measured values: C, 90.19; H, 4.94; N, 4.87; HRMS (ESI) m / z (M+H): theoretical value: 572.23, measured value: 574.16.

[0153] Synthesis Example 13 Compound C-56 was synthesized using the same method as in Example 1, except that starting material C14-A was used instead of starting material C1-A, and starting material C56-B was used instead of starting material C1-B. The synthetic route is shown in the following reaction formula: Compound C-56 was obtained in 88.3% yield. Elemental analysis: C 47 H 30 N2, theoretical values: C, 90.65; H, 4.86; N, 4.50; measured values: C, 90.66; H, 4.87; N, 4.48; HRMS (ESI) m / z (M+): theoretical value: 622.24, measured value: 623.28.

[0154] Synthesis Example 14 Compound C-71 was synthesized using the synthetic method of Example 1, except that starting material C14-a was used to replace starting material C1-A, and starting material C71-B was used to replace starting material C1-B. The synthetic route is shown in the following reaction formula:

[0155] Compound C-71 was obtained in 81.8% yield. Elemental analysis: C 37 H 24N2, theoretical values: C, 89.49; H, 4.87; N, 5.64; measured values: C, 89.51; H, 4.86; N, 5.63; HRMS (ESI) m / z (M+): theoretical value: 496.19, measured value: 497.11.

[0156] Synthesis Example 15 Synthesis of compound C-74:

[0157] In a 2-liter three-necked flask, under nitrogen protection, add starting material C14-a (220.00 mmol), starting material C74-B (200.00 mmol), potassium carbonate (500.00 mmol), dioxane (400 mL), water (100 mL), tetraphenylphosphine palladium (2.20 mmol), and 90 μL of other ingredients. The reaction was carried out at C for 12 hours. After the reaction was complete, the mixture was extracted with dichloromethane, dried over anhydrous sodium sulfate to remove the organic solvent, and then ethanol was added and stirred for 1 hour. The mixture was then filtered to obtain the crude product. The crude product was passed through a fast column chromatography with a mixed solvent (dichloromethane: tetrahydrofuran = 1:1), and then slurried with n-hexane to give C-74, with a yield of 83.8%. Elemental analysis: C 36 H 23 N3, theoretical values: C, 86.90; H, 4.66; N, 8.44; measured values: C, 86.92; H, 4.65; N, 8.43; HRMS (ESI) m / z (M+): theoretical value: 497.19, measured value: 498.22.

[0158] Component example: The materials used to prepare the following device embodiments or device comparative examples are shown in Table 2 below.

[0159] Table 2. Some compounds used in the device examples or device comparative examples

[0160] Device Example 1 This embodiment provides an organic electroluminescent device, such as... Figure 1As shown, it includes, in sequence, an anode 1, a hole injection layer 2, a first hole transport layer 3, a first electron blocking layer 4, a first organic light-emitting layer 5, a first hole blocking layer 6, a first electron transport layer 7, an n-type charge generation layer 8, a p-type charge generation layer 9, a second hole transport layer 10, a second electron blocking layer 11, a second organic light-emitting layer 12, a second hole blocking layer 13, a second electron transport layer 14, an electron injection layer 15, and a cathode 16. Its device structure is as follows: anode (indium tin oxide (ITO)), hole injection layer (HIL), first hole transport layer (HTL-1), first electron blocking layer (EBL-1), first organic light-emitting layer (EML-1), first hole blocking layer (HBL-1), first electron transport layer (ETL-1), n-type charge generation layer (CGL-n), p-type charge generation layer (CGL-p), second hole transport layer (HTL-2), second electron blocking layer (EBL-2), second organic light-emitting layer (EML-2), second hole blocking layer (HBL-2), second electron transport layer (ETL-2), electron injection layer (EIL), and cathode.

[0161] The fabrication of the above-mentioned organic electroluminescent device includes the following steps: 1) Substrate cleaning: The glass substrate coated with transparent ITO was ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: ethylene glycol solvent ≤10wt%, triethanolamine ≤1wt%), then rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol (volume ratio of acetone and ethanol 1:1), baked in a clean environment until all moisture was removed, and then cleaned with ultraviolet light and ozone.

[0162] 2) Preparation of the organic layer: The ITO transparent substrate was transferred to an evaporation equipment and vacuumed to 1×10⁻⁶. -6 Up to 2×10 -4 Pa, hole injection layer (HIL) / first hole transport layer (HTL-1) / first electron blocking layer (EBL-1) / first organic light-emitting layer (EML-1) / first hole blocking layer (HBL-1) / first electron transport layer (ETL-1) / n-type charge generation layer (CGL-n) / p-type charge generation layer (CGL-p) / second hole transport layer (HTL-2) / second electron blocking layer (EBL-2) / second organic light-emitting layer (EML-2) / second hole blocking layer (HBL-2) / second electron transport layer (ETL-2) / electron injection layer (EIL) / cathode (Mg:Ag mass ratio is 1:9) are deposited sequentially on the ITO anode film.

[0163] in: The anode is indium tin oxide (ITO, 10 nm thick); The hole injection layer (HIL) is made of HAT-CN:TCTA (10nm thick); the mass ratio of HAT-CN to TCTA is 3:97. The material of the first hole transport layer (HTL-1) is TCTA (20nm thick); The material of the first electron blocking layer (EBL-1) is mCP (5nm thick); The first organic light-emitting layer (EML-1) is made of D and E in a mass ratio of 95:5 (thickness 20nm); The material of the first hole blocking layer (HBL-1) is BCP (5nm thick); The first electron transport layer (ETL-1) is made of TPBI and LiQ in a mass ratio of 9:1 (thickness 25nm); The material of the n-type charge generation layer (CGL-n) is composed of compound C-1 and Yb from synthesis example 1, and its specific ratio and thickness are shown in Table 3. The p-type charge generation layer (CGL-p) is made of HAT-CN and TCTA in a mass ratio of 8:2 (thickness 10nm); The material of the second hole transport layer (HTL-2) is TCTA (20nm thick); The material of the second electron blocking layer (EBL-2) is mCP (5nm thick); The second organic light-emitting layer (EML-2) is made of D and E in a mass ratio of 95:5 (thickness 20nm); The material of the second hole blocking layer (HBL-2) is BCP (5nm thick); The second electron transport layer (ETL-2) is made of TPBI and LiQ in a mass ratio of 9:1 (thickness 25nm); The electron injection layer (EIL) is made of Yb (1 nm thick); The cathode is made of Mg and Ag in a mass ratio of 1:9 (thickness 11 nm).

[0164] Device Examples 2 to Device Examples 15 Device Examples 2 to 15 each provide an organic electroluminescent device, the preparation method of which is the same as that of Device Example 1, except that compound C-1 in the n-type charge generation layer of Device Example 1 is replaced with the compound obtained in Synthesis Examples 2 to 15. The composition and ratio of the compounds in the n-type charge generation layer of Device Examples 2 to 15 are shown in Table 3.

[0165] Device Comparison Examples 1 to 7 This comparative example provides an organic electroluminescent device, which is prepared in the same way as device example 1, except that compound C-1 in the n-type charge generation layer of device example 1 is replaced with compounds REF-1 to REF-7.

[0166] Table 3 Composition and thickness of n-type charge generation layer

[0167] The organic electroluminescent devices prepared in Device Examples 1-15 and Device Comparative Examples 1-7 in the device examples were tested.

[0168] Instruments: The current, voltage, brightness, emission spectrum and other characteristics of the device were tested simultaneously using a PR625 spectral scanning luminance meter and a Keithley K 2400 digital source meter system; Test conditions: Photoelectric property test conditions: current density 10 mA / cm² 2 , room temperature.

[0169] Lifetime test: Current density 10mA / cm 2 The recording time (in hours) is when the device brightness drops to 95% of its original brightness.

[0170] Among them, the lifetime and current efficiency of device comparison example 1 were set to 100. The test results of the lifetime and current efficiency of device examples 1-15 and device comparison examples 2-7 relative to device comparison example 1 are shown in Table 4. The test results of the driving voltage of device examples 1-15 and device comparison examples 1-7 are shown in Table 4.

[0171] Table 4. Device performance parameters for Device Examples 1-15 and Device Comparative Examples 1-7

[0172] Obviously, the above embodiments are merely illustrative examples for clear explanation and are not intended to limit the implementation. Those skilled in the art will recognize that other variations or modifications can be made based on the above description. It is neither necessary nor possible to exhaustively list all possible implementations here. However, obvious variations or modifications derived therefrom are still within the scope of protection of this invention.

Claims

1. An organic electroluminescent compound, characterized in that, It has the structure shown in equation (1): In formula (1), Ra and Rb are selected from the structure shown in formula (1-1) and the other is selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl. R 1 Selected from hydrogen or deuterium; n1 is an integer selected from 0 to 4; In equation (1-1), L 1 Selected from substituted or unsubstituted C6-C30 arylene, L 2 Selected from single bonds; R 2 and R 3 Each is independently selected from hydrogen or deuterium; n2 is selected from integers between 0 and 6; n3 is selected from integers from 0 to 9; The substituted C6-C30 aryl, substituted C3-C30 heteroaryl, and substituted C6-C30 arylene are each independently substituted by at least one of the following groups: deuterium, halogen, cyano, C1-C18 alkyl, C6-C30 aryl, and C3-C30 heteroaryl.

2. The organic electroluminescent compound according to claim 1, characterized in that, The organic electroluminescent compound has the structures shown in formulas (2) to (3) below: In the formula, Ra and Rb are each independently selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups; R 1 R 2 R 3 n1, n2, n3, L 1 L 2 The definition is the same as that in claim 1; The substituted C6-C30 aryl and the substituted C3-C30 heteroaryl are each independently substituted by at least one of the following groups: deuterium, halogen, cyano, C1-C18 alkyl, C6-C30 aryl, C3-C30 heteroaryl.

3. An organic electroluminescent compound according to claim 1 or 2, characterized in that, The organic electroluminescent compound has the structures shown in formulas (4) to (13); ； In the formula, Ra and Rb are each independently selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups; R 1 R 2 R 3 n1, n2, n3, L 1 L 2 The definition is the same as that in claim 1; The substituted C6-C30 aryl and the substituted C3-C30 heteroaryl are each independently substituted by at least one of the following groups: deuterium, halogen, cyano, C1-C18 alkyl, C6-C30 aryl, C3-C30 heteroaryl.

4. The organic electroluminescent compound according to claim 1, characterized in that, L 1 Selected from substituted or unsubstituted C6-C18 arylene groups; Wherein, the substituted C6-C18 arylene is substituted by at least one selected from the group consisting of: deuterium, halogen, cyano, C1-C12 alkyl, C6-C18 aryl; And / or, L 2 Selected from single bonds; And / or, Ra is selected from substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl; Wherein, the substituted C6-C18 aryl and the substituted C3-C18 heteroaryl are substituted by at least one of the following groups: deuterium, halogen, cyano, C1-C12 alkyl, C6-C18 aryl, C3-C18 heteroaryl; And / or, Rb is selected from substituted or unsubstituted C6-C18 aryl groups and substituted or unsubstituted C3-C18 heteroaryl groups; The substituted C6-C18 aryl group and the substituted C3-C18 heteroaryl group are substituted by at least one of the following groups: deuterium, halogen, cyano, C1-C12 alkyl, C6-C18 aryl, and C3-C18 heteroaryl.

5. The organic electroluminescent compound according to claim 1, characterized in that, L 1 Selected from substituted or unsubstituted C6-C12 arylene groups; Wherein, the substituted C6-C12 arylene is substituted by at least one selected from the group consisting of: deuterium, halogen, cyano, C1-C6 alkyl, C6-C12 aryl; And / or, L 2 Selected from single bonds; And / or, Ra is selected from substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C3-C12 heteroaryl; Wherein, the substituted C6-C12 aryl and the substituted C3-C12 heteroaryl are substituted by at least one of the following groups: deuterium, halogen, cyano, C1-C6 alkyl, C6-C12 aryl, C3-C12 heteroaryl; And / or, Rb is selected from substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C3-C12 heteroaryl; The substituted C6-C12 aryl group and the substituted C3-C12 heteroaryl group are substituted by at least one of the following groups: deuterium, halogen, cyano, C1-C6 alkyl, C6-C12 aryl, C3-C12 heteroaryl.

6. The organic electroluminescent compound according to claim 1, characterized in that, L 1 The group D is selected from substituted or unsubstituted groups, wherein the group D is selected from the group consisting of: ； Wherein, the substituted group D is substituted by at least one selected from the group consisting of: deuterium, tert-butyl, cyano, phenyl, naphthyl; And / or, L 2 Selected from single bonds; And / or, Ra is selected from substituted or unsubstituted group E, said group E being selected from the group consisting of: ； Wherein, the substituted group E is substituted by at least one selected from the group consisting of: deuterium, halogen, cyano, tert-butyl, phenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, dibenzofuranyl, dibenzothiopheneyl; And / or, Rb is selected from substituted or unsubstituted group G, said group G being selected from the group consisting of: ； Wherein, the substituted group G is substituted by at least one selected from the group consisting of: deuterium, halogen, cyano, tert-butyl, phenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, dibenzofuranyl, dibenzothiopheneyl.

7. The organic electroluminescent compound according to claim 1, characterized in that, The organic electroluminescent compound is selected from one of the following structures: 。 8. A charge-generating material, characterized in that, The charge-generating material includes any one or a combination of at least two of the organic electroluminescent compounds as described in any one of claims 1-7.

9. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes: a cathode; an anode disposed opposite to the cathode; and at least two light-emitting units between the cathode and the anode; wherein a charge-generating layer is provided between two adjacent light-emitting units, the charge-generating layer comprising an organic electroluminescent compound as described in any one of claims 1-7 or a charge-generating material as described in claim 8.

10. An organic electroluminescent device according to claim 9, characterized in that, The charge generation layer comprises an n-type charge generation layer and a p-type charge generation layer, wherein the n-type charge generation layer comprises an organic electroluminescent compound as described in any one of claims 1-7 or a charge generation material as described in claim 8.

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