An organic compound and use thereof

Abstract

The application belongs to the technical field of organic electroluminescence, and particularly relates to an organic compound and application thereof. The organic compound provided by the application is based on a mother nucleus in a structure of, and can have higher hole migration ability and better electrochemical stability as a whole by cooperating with different substituent groups, so that the carrier transport of an organic electroluminescence device containing the organic compound is more efficient, and the driving voltage is reduced, the current efficiency is improved, and the service life is prolonged.

Description

Technical Field

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

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

[0003] However, current OLED technology still faces several key challenges, mainly including high driving voltage requirements, insufficient luminous efficiency, and limited device lifetime, which restrict the widespread application and commercialization of organic electroluminescent devices. Therefore, developing novel organic electroluminescent materials to achieve low-voltage driving, high luminous efficiency output, and long-lifespan operation, thereby promoting the development of OLED technology to a higher level and expanding its application potential in display, lighting, and other fields, has become a top priority. Summary of the Invention

[0004] The purpose of this invention is to overcome the problems of high driving voltage, low luminous efficiency and short luminous lifetime of organic electroluminescent materials in organic electroluminescent devices in related technologies, and to provide an organic compound and its application.

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

[0006] The term "organic electroluminescent material" as used in this invention 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 refers to one or more organic electroluminescent materials comprising a combination of at least two compounds, said materials being contained in any layer constituting an organic electroluminescent device. It can mean both materials contained before (e.g., before vapor deposition) and materials contained after (e.g., after vapor deposition) the organic electroluminescent device. For example, multiple organic electroluminescent materials can be a combination of at least two compounds, said materials being contained in at least one of the following: a hole injection layer, a hole transport layer, a hole assist layer, a light-emitting assist layer, an electron blocking 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 can be contained in the same layer or different layers, and can be mixed-evaporated or co-evaporated, or can be evaporated individually.

[0008] 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.

[0009] 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-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, or C1-C60 heteroaryl. Optionally, it can be, for example, deuterium, a halogen group, cyano, alkyl, haloalkyl, trialkylsilyl, deuterated alkyl, aryl, heteroaryl, etc. Of course, the number of substituents Rc can be one or more. When two substituents Rc are attached to the same atom, the two substituents Rc can exist independently or be connected to each other to form a ring with the atom; when two adjacent substituents Rc exist on a functional group, the two adjacent substituents Rc can exist independently or fused with the functional group to which they are attached to form a ring.

[0010] 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-C60 alkyl" is derived from a monovalent substituent of a straight-chain or branched saturated hydrocarbon having 1 to 60 carbon atoms, preferably 1 to 40 carbon atoms, and more preferably 1 to 20 carbon atoms. Examples of such substituents include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.

[0011] In this invention, the term "C3-C60 cycloalkyl" refers to a cycloalkyl system consisting of at least 3 atoms. More specifically, it refers to a monocyclic or polycyclic hydrocarbon derived from a main chain of 3 to 60 carbon atoms, preferably 3 to 40 carbon atoms, and even more preferably 3 to 20 carbon atoms. Of course, the cycloalkyl includes, but is not limited to, cyclopropyl, cyclobutyl, adamantyl, etc.

[0012] 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, etc. Arylene groups include, but are not limited to, phenylene, biphenylene, terphenylene, naphthylene, phenanthrylene, anthraceneene, fluorene, and spirodifluorene, etc.

[0013] In this invention, the term "heteroaryl" includes monocyclic, polycyclic, or fused-ring heteroaryl groups, wherein the rings may be interrupted by short non-aromatic units, and the heteroatoms include nitrogen, oxygen, and sulfur. Heteroaryl groups in this invention include, but are not limited to, furanyl, phenylthio, pyrroleyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetraazinyl, triazolyl, tetraazolyl, furazolidyl, pyridinyl, pyrazinyl, and pyrimidine. Pyridyl, benzofuranyl, benzothiophene, isobenzofuranyl, dibenzofuranyl, dibenzothiophene, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisooxazolyl, benzooxazolyl, isoindolyl, indolyl, indazole, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxalolinyl, carbazole, phenoxazinyl, phenthiazinyl, phenanthidyl, benzo-m-dioxacyclopentenyl, dihydroacridyl And their derivatives, etc.; heteroaryl groups include, but are not limited to, pyrifos, pyrrolizyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridinyl, pyridazinyl, benzofuranyl, benzothiopheneyl, isobenzofuranyl, dibenzofuranyl Furanyl, dibenzothiophene, benzimidazolyl, benzithiazolyl, benzisisothiazolyl, benzisisooxazolyl, benzisoxazolyl, isoindolyl, indolyl, ininzolyl, benzisazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxolinyl, carbazolyl, phenoxazinyl, phenoxazinyl, phenanthridineyl, benzo[m]dioxacyclopentenyl, dihydroacridyl, and their derivatives, etc. As used herein, the term "substituted" means that a hydrogen atom in the compound is replaced by another substituent. This position is not limited to a specific position, as long as the hydrogen at that position can be replaced by a substituent. When two or more substituents are present, the two or more substituents can be the same or different.

[0014] In this invention, the term "halogen" refers to an atom selected from fluorine, chlorine, bromine, and iodine.

[0015] In this invention, unless otherwise stated, hydrogen atoms include protium, deuterium, and tritium.

[0016] In this invention, the definition of a group specifies a range of carbon atoms, and the number of carbon atoms is any integer within the defined range, such as C6-C60 aryl. The number of carbon atoms representing an aryl group can be any integer within the range of 6-60, such as 6, 8, 10, 13, 15, 17, 20, 22, 25, 30, 35, 40, 45, 50, 55 or 60, etc.

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

[0018] This invention provides an organic compound, the structure of which is shown in formula (1):

[0019]

[0020] In formula (1)

[0021] Either X or Y is O or S, and the other is N;

[0022] Ar 1 Selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, and substituted or unsubstituted C6-C60 aromatic amino groups;

[0023] Ar 2 Selected from substituted or unsubstituted C6-C60 aryl groups;

[0024] L 1 L 2 L 3 They are either the same or different, and are each independently selected from single-bonded, substituted or unsubstituted C6-C60 aryl groups;

[0025] The substituents of the substituted C6-C60 aryl, substituted C3-C60 heteroaryl, substituted C6-C60 aromatic amino, and substituted C6-C60 arylene are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroarylamine.

[0026] Preferably, the organic compound is selected from any one of formulas 1-1 to 1-4, wherein Ar 1 Ar 2 L 1 L 2 L 3 The definition is the same as above:

[0027]

[0028] Preferably, in formula (1) or formulas 1-1 to 1-4, Ar 1 Selected from substituted or unsubstituted C6-C45 aryl, substituted or unsubstituted C3-C45 heteroaryl, and substituted or unsubstituted C6-C45 aromatic amino groups;

[0029] Ar 2 Selected from substituted or unsubstituted C6-C45 aryl groups;

[0030] L 1 L 2 L 3 They are either the same or different, and are each independently selected from single-bonded, substituted or unsubstituted C6-C45 aryl groups;

[0031] The substituents of the substituted C6-C45 aryl, substituted C3-C45 heteroaryl, substituted C6-C45 aromatic amino, and substituted C6-C45 arylene are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaromatic amine.

[0032] Preferably, the substituents of the substituted C6-C45 aryl, substituted C3-C45 heteroaryl, substituted C6-C45 arylamine, and substituted C6-C45 arylene are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexyl, cyclopentyl, phenyl, naphthyl, biphenyl, anthracene, fluorenyl, pyrene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, and carbazole.

[0033] Preferably, in formula (1) or formulas 1-1 to 1-4, Ar 1 Selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and substituted or unsubstituted C6-C30 aromatic amino groups;

[0034] Ar 2 Selected from substituted or unsubstituted C6-C30 aryl groups;

[0035] L 1 L 2 L 3 They are either the same or different, and are each independently selected from single-bonded, substituted or unsubstituted C6-C30 aryl groups;

[0036] The substituents of the substituted C6-C30 aryl, substituted C3-C30 heteroaryl, substituted C6-C30 aromatic amino, and substituted C6-C30 arylene are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaromatic amine.

[0037] Preferably, the substituents of the substituted C6-C30 aryl, substituted C3-C30 heteroaryl, substituted C6-C30 arylamine, and substituted C6-C30 arylene are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexyl, cyclopentyl, phenyl, naphthyl, biphenyl, anthracene, fluorenyl, pyrene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, and carbazole.

[0038] Preferably, in formula (1) or formulas 1-1 to 1-4, Ar 1 Selected from substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, and substituted or unsubstituted C6-C20 aromatic amino groups;

[0039] Ar 2 Selected from substituted or unsubstituted C6-C20 aryl groups;

[0040] L 1 L 2 L 3 They are either the same or different, and are each independently selected from single-bonded, substituted or unsubstituted C6-C20 aryl groups;

[0041] The substituents of the substituted C6-C20 aryl, substituted C3-C20 heteroaryl, substituted C6-C20 aromatic amino, and substituted C6-C20 arylene are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaromatic amine.

[0042] Preferably, the substituents of the substituted C6-C20 aryl, substituted C3-C20 heteroaryl, substituted C6-C20 arylamine, and substituted C6-C20 arylene are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexyl, cyclopentyl, phenyl, naphthyl, biphenyl, anthracene, fluorenyl, pyrene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, and carbazole.

[0043] Preferably, in formula (1) or formulas 1-1 to 1-4, Ar 1 Selected from substituted or unsubstituted C6-C15 aryl, substituted or unsubstituted C3-C15 heteroaryl, and substituted or unsubstituted C6-C15 aromatic amino groups;

[0044] Ar 2 Selected from substituted or unsubstituted C6-C15 aryl groups;

[0045] L 1 L2 L 3 They may be the same or different, and each is independently selected from single-bonded, substituted or unsubstituted C6-C15 aryl groups;

[0046] The substituents of the substituted C6-C15 aryl, substituted C3-C15 heteroaryl, substituted C6-C15 aromatic amino, and substituted C6-C15 arylene are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroarylamine.

[0047] Preferably, the substituents of the substituted C6-C15 aryl, substituted C3-C15 heteroaryl, substituted C6-C15 arylamine, and substituted C6-C15 arylene are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexyl, cyclopentyl, phenyl, naphthyl, biphenyl, anthracene, fluorenyl, pyrene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, and carbazole.

[0048] Preferred, Ar 1 The A group is selected from substituted or unsubstituted groups, wherein the A group is selected from: phenyl, naphthyl, phenanthryl, anthracene, fluoranyl, pyrene, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothiophene, dibenzothiophene, naphthobenzothiophene, carbazolyl, phenylcarbazolyl, benzocarbazolyl, benzophenylcarbazolyl, dibenzocarbazolyl, biphenylcarbazolyl, phenanthrenebenzofuranyl, benzofuran-benzofuranyl, phenylcarbazo-benzofuranyl;

[0049] Ar 2 The B group is selected from substituted or unsubstituted groups, and the B group is selected from: phenyl, naphthyl, phenanthryl, anthracene, fluoranyl, pyrene, terphenyl, biphenyl, phenylnaphthyl, naphthylphenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl;

[0050] L 1 L 2 L 3Whether the groups are the same or different, each group is independently selected from single-bonded, substituted or unsubstituted C groups, and the C groups are selected from: phenylene, naphthylene, phenanthrene, anthracene, fluorenylene, pyrene, terphenylene, biphenylene, phenylenenaphthyl, naphthylphenylene, terphenylene, fluorene, dimethylfluorene, diphenylfluorene, spirodifluorene, benzo[2]dimethylfluorene, benzo[2]diphenylfluorene, benzo[2]spirodifluorene;

[0051] The substituents of the substituted A group, substituted B group, and substituted C group are each independently selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroarylamine.

[0052] Preferably, the substituents of the substituted A group, substituted B group, and substituted C group are each independently selected from one or a combination of at least two of the following: deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexyl, cyclopentyl, phenyl, naphthyl, phenanthryl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracene, fluorenyl, pyrene, fluoranyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzonaphthiofuranyl, benzonaphthiophene, carbazole, and benzocarbazole.

[0053] Preferred, L 1 L 3 Not at the same time

[0054] Preferably, in formula (1) or formulas 1-1 to 1-4, Ar 1 Selected from the group consisting of the following groups:

[0055]

[0056]

[0057]

[0058] Preferably, in formula (1) or formulas 1-1 to 1-4, Ar 2 Selected from the group consisting of the following groups:

[0059]

[0060]

[0061]

[0062] Preferably, in formula (1) or formulas 1-1 to 1-4, L 1 L2 L 3 Whether identical or different, each is independently selected from the group consisting of the following groups:

[0063]

[0064] Preferred, L 1 L 3 Not at the same time

[0065] Preferably, the organic compound is selected from any of the following structures:

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079] The present invention provides an organic electroluminescent material comprising the organic compounds described above.

[0080] Preferably, the organic electroluminescent material comprises a first host material and a second host material, wherein the first host material is the organic compound described above; and the second host material is an organic electroluminescent compound having the structure of formula (2) below:

[0081]

[0082] In equation (2), where X1-X 12 Each is independently selected from N or CR, and R is selected from hydrogen or deuterium;

[0083] L' is selected from the linking bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene;

[0084] R 1 R 2 Each is independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C60 aromatic amino, or substituted or unsubstituted C3-C60 heteroaryl;

[0085] The substituents in the substituted C6-C60 aryl, substituted C6-C60 aromatic amino, substituted C3-C60 heteroaryl, substituted C3-C30 heteroaryl, substituted C6-C30 arylene, substituted C3-C30 heteroarylene, substituted C6-C30 aryl, and substituted C3-C30 heteroaryl are selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0086] Preferred, R 1 R 2 Each group is independently selected from substituted or unsubstituted D groups, wherein the D group is selected from phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, triphenylene, etc. yl, dimethylfluorenyl, spirodifluorenyl, fluoranyl, diphenylfluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, phenylcarbazolyl, dipyridyl, pyrimidinyl, triazineyl;

[0087] Wherein, the substituents in the substituted D group are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaryl.

[0088] Preferred, R 1 R 2 Each is independently selected from phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, and triphenylene. , dimethylfluorenyl, spirodifluorenyl, fluoranyl, diphenylfluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, phenylcarbazolyl, dipyridyl, pyrimidinyl, triazineyl.

[0089] Preferably, in equation (2), L ’ It is a single bond;

[0090] Preferably, X1-X 12 Each was selected independently from CR;

[0091] Or, X1-X 12 X2 is selected from N, and the others are selected independently from CR;

[0092] Or, X1-X 12 X5 is selected from N, and the others are selected independently from CR;

[0093] Or, X1-X 12 X8 is selected from N, and the others are selected independently from CR;

[0094] Or, X1-X 12 X9 is selected from N, and the others are selected independently from CR.

[0095] Preferably, the second compound has any one of the structures shown below, from N-1 to N-348:

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102] Preferably, the mass ratio of the first main material to the second main material is 9:1 to 1:9;

[0103] Preferably, the mass ratio of the first main material to the second main material is 2:8-8:2;

[0104] More preferably, the mass ratio of the first main material to the second main material is 3:7-7:3;

[0105] More preferably, the mass ratio of the first main material to the second main material is 4:6-6:4.

[0106] The present invention provides an organic electroluminescent device, the organic electroluminescent device comprising an anode, a cathode and an organic layer located between the anode and the cathode, the organic layer comprising an organic compound as described above or an organic electroluminescent material as described above.

[0107] Preferably, the organic layer includes any one or a combination of at least two of the following: a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0108] Preferably, the organic layer includes a light-emitting layer, which comprises an organic compound as described above or an organic electroluminescent material as described above.

[0109] Preferably, the light-emitting layer comprises a host material and a guest material, wherein the host material comprises an organic compound as described above or an organic electroluminescent material as described above.

[0110] Preferably, the organic layer includes a light-emitting auxiliary layer, which includes an organic compound as described above or an organic electroluminescent material as described above.

[0111] Optionally, the organic electroluminescent device includes a red-light organic electroluminescent device;

[0112] Optionally, the organic electroluminescent device includes a blue organic electroluminescent device;

[0113] Optionally, the organic electroluminescent device includes a green organic electroluminescent device;

[0114] The present invention provides an electronic device, the electronic device comprising an organic electroluminescent device as described above, an organic compound as described above, or an organic electroluminescent material as described above.

[0115] The beneficial effects of this invention are:

[0116] The organic compound provided by this invention, based on the core in the structure of formula (1), can be combined with different substituents to enable the compound to have both high hole migration ability and good electrochemical stability, thereby making the carrier transport of the organic electroluminescent device containing the organic compound more efficient, thus reducing the driving voltage, improving the current efficiency and extending the lifetime. Attached Figure Description

[0117] 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.

[0118] Figure 1 This is a structural diagram of the organic electroluminescent device in the device embodiment of the present invention;

[0119] 1-Substrate; 2-Anode; 3-Hole injection layer; 4-Hole transport layer; 5-Light emission auxiliary layer; 6-Light emission layer; 7-Hole blocking layer; 8-Electron transport layer; 9-Electron injection layer; 10-Cathode. Detailed Implementation

[0120] 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.

[0121] Those skilled in the art will recognize that the chemical reactions described in this invention can be suitably used to prepare many of the heterocyclic compounds of this invention, and other methods for preparing the compounds of this invention are considered to be within the scope of this invention. For example, the synthesis of those non-illustrative compounds according to this invention can be successfully accomplished by those skilled in the art through modification methods, such as appropriate protection of interfering groups, by utilizing other known reagents besides those described in this invention, or by making some conventional modifications to the reaction conditions. Compounds for which synthetic methods are not mentioned in this invention are commercially available starting materials.

[0122] In this invention, the compound represented by formula (1) is prepared via the following synthetic route:

[0123]

[0124] The starting materials ax, bx, and cx can be purchased directly or synthesized using conventional reaction pathways and conditions by referring to existing literature reports.

[0125] The specific structures of the raw materials ax, bx, and cx used in this embodiment of the invention are as follows:

[0126] The specific structure of raw material ax is as follows:

[0127]

[0128] The specific structure of raw material bx is as follows:

[0129]

[0130] The specific structure of the raw material CX is as follows:

[0131]

[0132]

[0133] Example 1:

[0134] This invention provides a method for preparing compound P-2, comprising the following steps:

[0135]

[0136] Synthesis of intermediate sub-2: A 100 mL three-necked round-bottom flask was placed with a stir bar and a reflux tube attached. Under nitrogen protection, starting material a-1 (1 mmol), starting material b-1 (1.05 mmol), tris(dibenzylacetone)palladium (0.03 mmol), Xphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), and toluene (10 mL) were added sequentially. The mixture was heated to 110 °C and reacted for 5 hours. After the reaction was completed, the mixture was cooled to room temperature and quenched with saturated ammonium chloride aqueous solution. The mixture was extracted with ethyl acetate, and the organic phase was dried over anhydrous magnesium sulfate. The solvent was removed using a rotary evaporator. The crude product was separated by column chromatography (ethyl acetate: n-hexane = 3:50) to obtain intermediate sub-2 (yield 80%).

[0137] Synthesis of compound P-2: A 100 mL three-necked round-bottom flask was placed with a stir bar and a reflux tube attached. Under nitrogen protection, intermediate sub-2 (1 mmol), c-1 (1.1 mmol), tris(dibenzylacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), and toluene (10 mL) were added sequentially. The mixture was heated to 110 °C and reacted for 5 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered, and the filter cake was washed twice with deionized water and twice with ethanol. The crude product was then purified twice by recrystallization from toluene and tetrahydrofuran, respectively, to obtain compound P-2 (yield 55%).

[0138] Elemental analysis: C 51 H 34 N₂O; Theoretical values: C, 88.67; H, 4.96; N, 4.06; O, 2.32; Measured values: C, 88.63; H, 4.99; N, 4.07; HRMS(ESI) m / z [M+H] + Theoretical value: 690.85; Measured value: 691.83.

[0139] Example 2-Example 3

[0140] Examples 2-3 utilize intermediate sub-2 and, by replacing different starting materials cx, compounds P-79 and P-129 can be obtained. The specific structures of the compounds are shown in Table 1 below.

[0141] Table 1

[0142]

[0143]

[0144] The elemental analysis results of compounds P-79 and P-129 are shown in Table 2 below:

[0145] Table 2

[0146]

[0147] Example 4:

[0148] This invention provides a method for preparing compound P-5, comprising the following steps:

[0149]

[0150] Synthesis of intermediate sub-5: The synthesis steps of intermediate sub-5 are the same as those of intermediate sub-2, except that raw material b-1 is replaced with raw material b-2, thus obtaining intermediate sub-5 (yield 79%).

[0151] Synthesis of compound P-5: The synthesis steps of compound P-5 are the same as those of compound P-2, except that intermediate sub-2 is replaced with intermediate sub-5 and starting material c-1 is replaced with starting material c-2, thus obtaining compound P-5 (yield 56%).

[0152] Elemental analysis: C 53 H 36 N₂O; Theoretical values: C, 88.80; H, 5.06; N, 3.91; O, 2.23; Measured values: C, 88.82; H, 5.08; N, 3.86; HRMS(ESI) m / z [M+H] + Theoretical value: 716.88; Measured value: 717.89.

[0153] Example 5:

[0154] This invention provides a method for preparing compound P-23, comprising the following steps:

[0155]

[0156] Synthesis of intermediate sub-23: The synthesis steps of intermediate sub-23 are the same as those of intermediate sub-2, except that raw material a-1 is replaced with raw material a-2 and raw material b-1 is replaced with raw material b-3, thus obtaining intermediate sub-23 (yield 84%).

[0157] Synthesis of compound P-23: The synthesis steps of compound P-23 are the same as those of compound P-2, except that intermediate sub-2 is replaced with intermediate sub-23 and starting material c-1 is replaced with starting material c-3, thus obtaining compound P-23 (yield 53%).

[0158] Elemental analysis: C 55 H 36 N₂O; Theoretical values: C, 89.16; H, 4.90; N, 3.78; O, 2.16; Measured values: C, 89.13; H, 4.91; N, 3.79; HRMS(ESI) m / z [M+H] + Theoretical value: 740.91; Measured value: 741.90.

[0159] Example 6:

[0160] This invention provides a method for preparing compound P-144, comprising the following steps:

[0161]

[0162] Synthesis of intermediate sub-144: The synthesis steps of intermediate sub-144 are the same as those of intermediate sub-2, except that raw material b-1 is replaced with raw material b-4, thus obtaining intermediate sub-144 (yield 79%).

[0163] Synthesis of compound P-144: The synthesis steps of compound P-144 are the same as those of compound P-2, except that intermediate sub-2 is replaced with intermediate sub-144 and starting material c-1 is replaced with starting material c-6, thus obtaining compound P-144 (yield 55%).

[0164] Elemental analysis: C 57 H 38 N₂O; Theoretical values: C, 89.27; H, 4.99; N, 3.65; O, 2.09; Measured values: C, 89.24; H, 5.00; N, 3.66; HRMS(ESI) m / z [M+H] + Theoretical value: 766.94; Measured value: 767.95.

[0165] Example 7:

[0166] This invention provides a method for preparing compound P-158, comprising the following steps:

[0167]

[0168] Synthesis of intermediate sub-158: The synthesis steps of intermediate sub-158 are the same as those of intermediate sub-2, except that raw material a-1 is replaced with raw material a-2 and raw material b-1 is replaced with raw material b-4, thus obtaining intermediate sub-158 (yield 78%).

[0169] Synthesis of compound P-158: The synthesis steps of compound P-158 are the same as those of compound P-2, except that intermediate sub-2 is replaced with intermediate sub-158 and starting material c-1 is replaced with starting material c-6, thus obtaining compound P-158 (yield 52%).

[0170] Elemental analysis: C 53 H 36 N₂O; Theoretical values: C, 88.80; H, 5.06; N, 3.91; O, 2.23; Measured values: C, 88.82; H, 5.08; N, 3.86; HRMS(ESI) m / z [M+H] + Theoretical value: 716.88; Measured value: 717.89.

[0171] Example 8:

[0172] This invention provides a method for preparing compound P-160, comprising the following steps:

[0173]

[0174] Synthesis of intermediate sub-160: The synthesis steps of intermediate sub-160 are the same as those of intermediate sub-2, except that raw material a-1 is replaced with raw material a-4 and raw material b-1 is replaced with raw material b-6, thus obtaining intermediate sub-160 (yield 79%).

[0175] Synthesis of compound P-160: The synthesis steps of compound P-160 are the same as those of compound P-2, except that intermediate sub-2 is replaced with intermediate sub-160 and starting material c-1 is replaced with starting material c-7, thus obtaining compound P-160 (yield 52%).

[0176] Elemental analysis: C 56 H 40 N₂O; Theoretical values: C, 88.86; H, 5.33; N, 3.70; O, 2.11; Measured values: C, 88.82; H, 5.34; N, 3.71; HRMS(ESI) m / z [M+H] + Theoretical value: 756.31; Measured value: 757.66.

[0177] Example 9:

[0178] This invention provides a method for preparing compound P-173, comprising the following steps:

[0179]

[0180] Synthesis of intermediate sub-173: The synthesis steps of intermediate sub-173 are the same as those of intermediate sub-2, except that raw material a-1 is replaced with raw material a-6 and raw material b-1 is replaced with raw material b-7, thus obtaining intermediate sub-173 (yield 81%).

[0181] Synthesis of compound P-173: The synthesis steps of compound P-173 are the same as those of compound P-2, except that intermediate sub-2 is replaced with intermediate sub-173 and starting material c-1 is replaced with starting material c-8, thus obtaining compound P-173 (yield 54%).

[0182] Elemental analysis: C 51 H 34 N₂S; Theoretical values: C, 86.65; H, 4.85; N, 3.96; S, 4.54; Measured values: C, 86.64; H, 4.81; N, 3.99; HRMS(ESI) m / z [M+H] + Theoretical value: 706.24; Measured value: 707.84.

[0183] Example 10:

[0184] This invention provides a method for preparing compound P-229, comprising the following steps:

[0185]

[0186] Synthesis of intermediate sub-229: The synthesis steps of intermediate sub-229 are the same as those of intermediate sub-2, except that raw material a-1 is replaced with raw material a-4 and raw material b-1 is replaced with raw material b-8, thus obtaining intermediate sub-229 (yield 79%).

[0187] Synthesis of compound P-229: The synthesis steps of compound P-229 are the same as those of compound P-2, except that intermediate sub-2 is replaced with intermediate sub-229 and starting material c-1 is replaced with starting material c-6, thus obtaining compound P-229 (yield 55%).

[0188] Elemental analysis: C 55 H 36 N₂O; Theoretical values: C, 89.16; H, 4.90; N, 3.78; O, 2.16; Measured values: C, 89.13; H, 4.91; N, 3.79; HRMS(ESI) m / z [M+H] + Theoretical value: 740.91; Measured value: 741.90.

[0189] Example 11:

[0190] This invention provides a method for preparing compound P-332, comprising the following steps:

[0191]

[0192] Synthesis of intermediate sub-332: The synthesis steps of intermediate sub-332 are the same as those of intermediate sub-2, except that raw material a-1 is replaced with raw material a-5 and raw material b-1 is replaced with raw material b-6, thus obtaining intermediate sub-332 (yield 81%).

[0193] Synthesis of compound P-332: The synthesis steps of compound P-332 are the same as those of compound P-2, except that intermediate sub-2 is replaced with intermediate sub-332 and starting material c-1 is replaced with starting material c-6, thus obtaining compound P-332 (yield 51%).

[0194] Elemental analysis: C 53 H 36 N₂O; Theoretical values: C, 88.80; H, 5.06; N, 3.91; O, 2.23; Measured values: C, 88.02; H, 5.01; N, 3.92; HRMS(ESI) m / z [M+H] + Theoretical value: 690.85; Measured value: 691.83.

[0195] Example 12:

[0196] This invention provides a method for preparing compound P-343, comprising the following steps:

[0197]

[0198] Synthesis of intermediate sub-343: The synthesis steps of intermediate sub-343 are the same as those of intermediate sub-2, except that raw material a-1 is replaced with raw material a-6 and raw material b-1 is replaced with raw material b-2, thus obtaining intermediate sub-343 (yield 83%).

[0199] Synthesis of compound P-343: The synthesis steps of compound P-343 are the same as those of compound P-2, except that intermediate sub-2 is replaced with intermediate sub-343 and starting material c-1 is replaced with starting material c-9, thus obtaining compound P-343 (yield 50%).

[0200] Elemental analysis: C 53 H 34N₂O₂; Theoretical values: C, 87.10; H, 4.69; N, 3.83; O, 4.38; Measured values: C, 87.12; H, 4.70; N, 3.79; HRMS(ESI) m / z [M+H] + Theoretical value: 730.87; Measured value: 731.88.

[0201] Example 13:

[0202] This invention provides a method for preparing compound P-414, comprising the following steps:

[0203]

[0204] Synthesis of intermediate sub-414: The synthesis steps of intermediate sub-414 are the same as those of intermediate sub-2, except that raw material a-1 is replaced with raw material a-7 and raw material b-1 is replaced with raw material b-6, thus obtaining intermediate sub-414 (yield 78%).

[0205] Synthesis of compound P-414: The synthesis steps of compound P-414 are the same as those of compound P-2, except that intermediate sub-2 is replaced with intermediate sub-414 and starting material c-1 is replaced with starting material c-10, thus obtaining compound P-414 (yield 54%).

[0206] Elemental analysis: C 47 H 32 N₂O; Theoretical values: C, 88.10; H, 5.03; N, 4.37; O, 2.50; Measured values: C, 88.11; H, 5.04; N, 4.34; HRMS(ESI) m / z [M+H] + Theoretical value: 640.79; Measured value: 641.80.

[0207] Example 14:

[0208] This invention provides a method for preparing compound P-416, comprising the following steps:

[0209]

[0210] Synthesis of compound P-416: The synthesis steps of compound P-416 are the same as those of compound P-2, except that intermediate sub-2 is replaced with intermediate sub-414 and starting material c-1 is replaced with starting material c-6, thus obtaining compound P-416 (yield 52%).

[0211] Elemental analysis: C 47 H 32N₂O; Theoretical values: C, 88.10; H, 5.03; N, 4.37; O, 2.50; Measured values: C, 88.11; H, 5.04; N, 4.34; HRMS(ESI) m / z [M+H] + Theoretical value: 640.79; Measured value: 641.80.

[0212] Device Examples

[0213] This invention also provides OLED devices composed of different organic electroluminescent materials, with specific structural distributions 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 on the glass substrate) / hole injection layer 3 (HIL) / hole transport layer 4 (HTL) / light-emitting auxiliary layer 5 (EBL) / light-emitting layer 6 (EML) / hole blocking layer 7 (HBL) / electron transport layer 8 (ETL) / electron injection layer (EIL) 9 / cathode 10.

[0214] Device Examples 1-20 and Device Comparative Examples 1-6

[0215] Optionally, the organic compound provided by the present invention can be used as a light-emitting layer material in a red OLED device. When the organic compound provided by the present invention is used as a light-emitting layer material in a red OLED device, the device material and structure are as follows:

[0216]

[0217]

[0218] The synthesis steps of materials REF-1, REF-2, and REF-3 used in the comparative examples of the devices in this invention are as follows. The intermediates and raw materials used are the same as those in the synthesis examples. The additional raw materials involved can be directly purchased or synthesized by referring to existing literature reports through conventional reaction routes and conditions:

[0219] 1. Preparation of REF-1

[0220]

[0221] Synthesis of compound REF-1: The synthesis steps of compound REF-1 are the same as those of compound P-2, except that the starting material c-1 is replaced with the starting material c-11 to obtain compound REF-1 (yield 47%).

[0222] Elemental analysis: C 51 H 34N₂O; Theoretical values: C, 88.67; H, 4.96; N, 4.06; O, 2.32; Measured values: C, 88.61; H, 5.00; N, 4.05; HRMS(ESI) m / z [M+H] + Theoretical value: 690.27; Measured value: 691.33.

[0223] 2. Preparation of REF-2

[0224]

[0225] Synthesis of intermediate sub-REF-2: The synthesis steps of intermediate sub-REF-2 are the same as those of intermediate sub-2, except that raw material b-1 is replaced with raw material b-8, thus obtaining intermediate sub-REF-2 (yield 79%).

[0226] Synthesis of compound REF-2: The synthesis steps of compound REF-2 are the same as those of compound P-2, except that intermediate sub-2 is replaced with intermediate sub-REF-2 to obtain compound REF-2 (yield 51%).

[0227] Elemental analysis: C 53 H 34 N₂O₂; Theoretical values: C, 87.10; H, 4.69; N, 3.83; O, 4.38; Measured values: C, 87.12; H, 4.72; N, 3.79; HRMS(ESI) m / z [M+H] + Theoretical value: 730.26; Measured value: 731.48.

[0228] 3. Preparation of REF-3

[0229]

[0230] Synthesis of intermediate sub-REF-3: The synthesis steps of intermediate sub-REF-3 are the same as those of intermediate sub-2, except that raw material a-1 is replaced with raw material a-8 and raw material b-1 is replaced with raw material b-2, thus obtaining intermediate sub-REF-3 (yield 77%).

[0231] Synthesis of compound REF-3: The synthesis steps of compound REF-3 are the same as those of compound P-2, except that intermediate sub-2 is replaced with intermediate sub-REF-3 and starting material c-1 is replaced with starting material c-2, thus obtaining compound REF-3 (yield 48%).

[0232] Elemental analysis: C 43 H 30N₂O₂; Theoretical values: C, 87.43; H, 5.12; N, 4.74; O, 2.71; Measured values: C, 87.42; H, 5.10; N, 4.75; HRMS(ESI) m / z [M+H] + Theoretical value: 590.24; Measured value: 591.67.

[0233] The fabrication of devices in Examples 1-20 and Comparative Examples 1-6 includes the following steps:

[0234] (1) Substrate cleaning:

[0235] The glass substrate coated with transparent ITO was ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: ethylene glycol solvent ≤10wt%, triethanolamine ≤1wt%), rinsed in deionized water, ultrasonically degreased in an acetone:ethanol mixed solvent (volume ratio 1:1), baked in a clean environment until all moisture was removed, and then cleaned with ultraviolet light and ozone.

[0236] (2) Evaporation of organic light-emitting functional layer:

[0237] The glass substrate with the anode layer was placed in a vacuum chamber and evacuated to a vacuum level of 1×10⁻⁶. -6 Up to 2×10 -4 Pa, a mixture of HATCN and HT1 is vacuum-deposited on the above-mentioned anodic layer film, wherein the mass ratio of HATCN to HT1 is 3:97, as a hole injection layer, and the deposition thickness is 10 nm.

[0238] A hole transport layer (material HT1) is deposited on the hole injection layer, with a film thickness of 80 nm.

[0239] A light-emitting auxiliary layer (made of TCTA) is deposited on the hole transport layer, with a deposition thickness of 5 nm.

[0240] The light-emitting layer is deposited on the light-emitting auxiliary layer. The specific preparation method is as follows: the light-emitting host material (the material is shown in Table 3) and the guest material (piq)2Ir(acac) are vacuum deposited by co-evaporation, and the total film thickness is 35nm.

[0241] A hole blocking layer (material TPPB) is deposited on the light-emitting layer, with a deposition thickness of 5 nm.

[0242] An electron transport layer is deposited on the hole blocking layer. The specific preparation method is as follows: ET1 and LiQ are vacuum deposited by co-evaporation, and the total film thickness is 30 nm.

[0243] An electron injection layer (LiQ material) was vacuum-deposited on the electron transport layer, with a total film thickness of 1 nm.

[0244] Al was deposited on the electron injection layer as a cathode, with a total film thickness of 90 nm.

[0245] The parameters of each layer, its material, and its thickness in the device are shown in Table 3 below:

[0246] Table 3

[0247]

[0248]

[0249]

[0250] The organic electroluminescent devices obtained in Device Examples 1-20 and Device Comparative Examples 1-6 were tested.

[0251] Instruments: The current, voltage, brightness, emission spectrum and other characteristics of the device were tested simultaneously using a PR650 spectral scanning luminance meter and a Keithley K2400 digital source meter system;

[0252] Test conditions: Photoelectric property test conditions: current density 10 mA / cm² 2 .

[0253] Lifetime test: Current density 50mA / cm 2 The recording time (in hours) is recorded when the device brightness drops to 95% of its original brightness.

[0254] The device performance test results are shown in Table 4. To better demonstrate the performance advantages of this invention, all test data of Comparative Example 1 are set to 100. The data in the table below are all ratios to Comparative Example 1:

[0255] Table 4

[0256]

[0257]

[0258] Device Examples 21-28 and Device Comparative Examples 7-9

[0259] Optionally, the organic compound provided by the present invention can be used as a light-emitting auxiliary layer material in a red OLED device. When the organic compound provided by the present invention is used as a light-emitting auxiliary layer material in a red OLED device, the device material and structure are as follows:

[0260]

[0261]

[0262] The fabrication of devices in Examples 21-28 and Comparative Examples 7-9 includes the following steps:

[0263] (1) Substrate cleaning:

[0264] The glass substrate coated with transparent ITO was ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: ethylene glycol solvent ≤10wt%, triethanolamine ≤1wt%), rinsed in deionized water, ultrasonically degreased in an acetone:ethanol mixed solvent (volume ratio 1:1), baked in a clean environment until all moisture was removed, and then cleaned with ultraviolet light and ozone.

[0265] (2) Evaporation of organic light-emitting functional layer:

[0266] The glass substrate with the anode layer was placed in a vacuum chamber and evacuated to a vacuum level of 1×10⁻⁶. -6 Up to 2×10 -4 Pa, a mixture of HATCN and HT1 is vacuum-deposited on the above-mentioned anodic layer film, wherein the mass ratio of HATCN to HT1 is 3:97, as a hole injection layer, and the deposition thickness is 10 nm.

[0267] A hole transport layer (material HT1) is deposited on the hole injection layer, with a film thickness of 80 nm.

[0268] A light-emitting auxiliary layer (the material of which is shown in Table 5) is deposited on the hole transport layer, and the thickness of the deposited film is 5 nm.

[0269] The light-emitting layer is deposited on the light-emitting auxiliary layer. The specific preparation method is as follows: the light-emitting host material CBP or the organic compound and guest material (piq)2Ir(acac) of the present invention are vacuum deposited by co-evaporation (the materials are shown in Table 5), and the total film thickness is 35nm.

[0270] A hole blocking layer (material TPPB) is deposited on the light-emitting layer, with a deposition thickness of 5 nm.

[0271] An electron transport layer is deposited on the hole blocking layer. The specific preparation method is as follows: ET1 and LiQ are vacuum deposited by co-evaporation, and the total film thickness is 30 nm.

[0272] An electron injection layer (LiQ material) was vacuum-deposited on the electron transport layer, with a total film thickness of 1 nm.

[0273] Al was deposited on the electron injection layer, with a total film thickness of 90 nm.

[0274] The parameters of each layer, its material, and its thickness in the device are shown in Table 5 below:

[0275] Table 5

[0276]

[0277]

[0278] The organic electroluminescent devices obtained in Device Examples 21-28 and Device Comparative Examples 7-9 were tested.

[0279] Instruments: The current, voltage, brightness, emission spectrum and other characteristics of the device were tested simultaneously using a PR650 spectral scanning luminance meter and a Keithley K2400 digital source meter system;

[0280] Test conditions: Photoelectric property test conditions: current density 10 mA / cm² 2 .

[0281] Lifetime test: Current density 50mA / cm 2 The recording time (in hours) is recorded when the device brightness drops to 95% of its original brightness.

[0282] The device performance test results are shown in Table 6. To better demonstrate the performance advantages of this invention, all test data in Comparative Example 7 in Table 6 are set to 100, and all data in Table 6 are ratios to it.

[0283] Table 6

[0284] project Drive voltage Current efficiency Lifespan T95 Device Example 21 94.4 104.7 103.5 Device Example 22 95.2 104.9 102.4 Device Example 23 94.5 103.4 103.1 Device Example 24 93.4 106.6 104.2 Device Example 25 96.6 101.2 101.5 Device Example 26 95.3 104.4 102.9 Device Example 27 82.6 159.7 159.4 Device Example 28 79.8 177.5 168.0 Device Comparison Example 7 100 100 100 Device Comparison Example 8 102.9 98.4 98.5 Device Comparison Example 9 98.9 100.2 100.7

[0285] Device Examples 29-35 and Device Comparative Examples 10-12

[0286] Optionally, the organic compound provided by the present invention can be used as a light-emitting auxiliary layer material in blue OLED devices. When the organic compound provided by the present invention is used as a light-emitting auxiliary layer material in blue OLED devices, the device material and structure are as follows:

[0287]

[0288]

[0289] The fabrication of devices in Examples 29-35 and Comparative Examples 10-12 includes the following steps:

[0290] (1) Substrate cleaning:

[0291] The glass substrate coated with transparent ITO was ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: ethylene glycol solvent ≤10wt%, triethanolamine ≤1wt%), rinsed in deionized water, ultrasonically degreased in an acetone:ethanol mixed solvent (volume ratio 1:1), baked in a clean environment until all moisture was removed, and then cleaned with ultraviolet light and ozone.

[0292] (2) Evaporation of organic light-emitting functional layer:

[0293] The glass substrate with the anode layer was placed in a vacuum chamber and evacuated to a vacuum level of 1×10⁻⁶. -6 Up to 2×10 -4 Pa, a mixture of HT2 and HI is vacuum-deposited on the above-mentioned anodic layer film, wherein the mass ratio of HI to HT2 is 3:97, as a hole injection layer, and the deposition thickness is 10 nm.

[0294] A hole transport layer (material HT2) is deposited on the hole injection layer, with a film thickness of 80 nm.

[0295] A light-emitting auxiliary layer (materials shown in Table 7) was deposited on the hole transport layer, with a deposition thickness of 5 nm.

[0296] A light-emitting layer is deposited on the light-emitting auxiliary layer. The specific preparation method is as follows: the light-emitting host material BH and the guest material BD are vacuum-deposited by co-evaporation, and the total film thickness is 20nm.

[0297] A hole blocking layer (material HB) is deposited on the light-emitting layer, and the thickness of the deposited film is 5nm.

[0298] An electron transport layer is deposited on the hole blocking layer. The specific preparation method is as follows: ET2 and LiQ are vacuum deposited by co-evaporation, and the total film thickness is 30nm.

[0299] An electron injection layer (LiF material) was vacuum-deposited on the electron transport layer, with a total film thickness of 1 nm.

[0300] Al was deposited on the electron injection layer, with a total film thickness of 90 nm.

[0301] The parameters of each layer, its material, and its thickness in the device are shown in Table 7 below:

[0302] Table 7

[0303]

[0304]

[0305] The organic electroluminescent devices obtained in Device Examples 29-35 and Device Comparative Examples 10-12 were tested.

[0306] Instruments: The current, voltage, brightness, emission spectrum and other characteristics of the device were tested simultaneously using a PR650 spectral scanning luminance meter and a Keithley K2400 digital source meter system;

[0307] Test conditions: Photoelectric property test conditions: current density 10 mA / cm² 2 .

[0308] Lifetime test: Current density 50mA / cm 2 The recording time (in hours) is recorded when the device brightness drops to 95% of its original brightness.

[0309] The device performance test results are shown in Table 8. To better demonstrate the performance advantages of this invention, all test data in Comparative Example 10 in Table 8 are set to 100, and all data in Table 8 are ratios to it.

[0310] Table 8

[0311] project Drive voltage Current efficiency Lifespan T95 Device Example 29 94.3 108.3 104.2 Device Example 30 95.4 106.5 103.5 Device Example 31 93.5 107.9 104.0 Device Example 32 95.1 105.5 104.7 Device Example 33 95.3 105.4 106.3 Device Example 34 97.3 103.8 103.3 Device Example 35 95.5 105.9 105.6 Device Comparison Example 10 100 100 100 Device Comparison Example 11 103.2 94.2 97.3 Device Comparison Example 12 97.9 101.3 100.9

[0312] The presence of naphthyl or substituted naphthyl groups in the structure of the organic compounds described in this invention enables the compounds to possess both high hole migration capability and good electrochemical stability. Therefore, when the organic compounds described in this invention are used as the host material, the charge transport of OLED devices becomes more efficient, thereby reducing driving voltage, improving current efficiency, and extending lifetime.

[0313] At the same time, through the design formula (1) Ar 2 L 1 L 2 L 3 Because the aryl group does not contain heteroatoms, the dipole moment within the organic compound molecule will be relatively reduced. Therefore, when this compound is used as a light-emitting auxiliary layer material, the layer structure can effectively block electrons, thereby efficiently transporting holes and ultimately increasing the probability of exciton recombination, thus improving the current efficiency of the device.

[0314] Obviously, the above embodiments are merely illustrative examples for clear explanation and are not intended to limit the implementation. Those skilled in the art will recognize that other variations or modifications can be made based on the above description. It is neither necessary nor possible to exhaustively list all possible implementations here. However, obvious variations or modifications derived therefrom are still within the scope of protection of this invention.

Claims

1. An organic compound, characterized in that, The structure of the organic compound is shown in formula (1): In formula (1) Either X or Y is O or S, and the other is N; Ar 1 Selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, and substituted or unsubstituted C6-C60 aromatic amino groups; Ar 2 Selected from substituted or unsubstituted C6-C60 aryl groups; L 1 L 2 L 3 They are either the same or different, and are each independently selected from single-bonded, substituted or unsubstituted C6-C60 aryl groups; The substituents of the substituted C6-C60 aryl, substituted C3-C60 heteroaryl, substituted C6-C60 aromatic amino, and substituted C6-C60 arylene are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroarylamine.

2. The organic compound according to claim 1, characterized in that, The organic compound is selected from any one of the structures of formulas 1-1 to 1-4, wherein Ar 1 Ar 2 L 1 L 2 L 3 The definition is the same as in claim 1:

3. The organic compound according to claim 1 or 2, characterized in that, Ar 1 Selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and substituted or unsubstituted C6-C30 aromatic amino groups; Ar 2 Selected from substituted or unsubstituted C6-C30 aryl groups; L 1 L 2 L 3 They are either the same or different, and are each independently selected from single-bonded, substituted or unsubstituted C6-C30 aryl groups; The substituents of the substituted C6-C30 aryl, substituted C3-C30 heteroaryl, substituted C6-C30 aromatic amino, and substituted C6-C30 arylene are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaromatic amine.

4. The organic compound according to any one of claims 1-3, characterized in that, Ar 1 The A group is selected from substituted or unsubstituted groups, wherein the A group is selected from: phenyl, naphthyl, phenanthryl, anthracene, fluoranyl, pyrene, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothiophene, dibenzothiophene, naphthobenzothiophene, carbazolyl, phenylcarbazolyl, benzocarbazolyl, benzophenylcarbazolyl, dibenzocarbazolyl, biphenylcarbazolyl, phenanthrenebenzofuranyl, benzofuran-benzofuranyl, phenylcarbazo-benzofuranyl; Ar 2 The B group is selected from substituted or unsubstituted groups, and the B group is selected from: phenyl, naphthyl, phenanthryl, anthracene, fluoranyl, pyrene, terphenyl, biphenyl, phenylnaphthyl, naphthylphenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl; L 1 L 2 L 3 Whether the groups are the same or different, each group is independently selected from single-bonded, substituted or unsubstituted C groups, and the C groups are selected from: phenylene, naphthylene, phenanthrene, anthracene, fluorenylene, pyrene, terphenylene, biphenylene, phenylenenaphthyl, naphthylphenylene, terphenylene, fluorene, dimethylfluorene, diphenylfluorene, spirodifluorene, benzo[2]dimethylfluorene, benzo[2]diphenylfluorene, benzo[2]spirodifluorene; Wherein, the substituents of the substituted A group, substituted B group, and substituted C group are each independently selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroarylamine; preferably, the substitution of the substituted A group, substituted B group, and substituted C group... Each of the radicals is independently selected from one or a combination of at least two of the following: deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexyl, cyclopentyl, phenyl, naphthyl, phenanthryl, phenylnaphthyl, naphthylphenyl, biphenyl, anthracene, fluorenyl, pyrene, fluoranyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzonaphthiofuranyl, benzonaphthiophene, carbazole, and benzocarbazole.

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

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

7. The organic electroluminescent material according to claim 6, characterized in that, The organic electroluminescent material comprises a first host material and a second host material, wherein the first host material is an organic compound as described in any one of claims 1-5; and the second host material is an organic electroluminescent compound having the structure of formula (2) below: In equation (2), X1-X12 are each independently selected from N or CR, and R is selected from hydrogen or deuterium; L' is selected from the linking bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene; R 1 R 2 Each is independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C60 aromatic amino, or substituted or unsubstituted C3-C60 heteroaryl; The substituents in the substituted C6-C60 aryl, substituted C6-C60 aromatic amino, substituted C3-C60 heteroaryl, substituted C3-C30 heteroaryl, substituted C6-C30 arylene, substituted C3-C30 heteroarylene, substituted C6-C30 aryl, and substituted C3-C30 heteroaryl are selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl. Preferred, R 1 R 2 Each group is independently selected from substituted or unsubstituted D groups, wherein the D group is selected from phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, triphenylene, etc. yl, dimethylfluorenyl, spirodifluorenyl, fluoranyl, diphenylfluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, phenylcarbazolyl, dipyridyl, pyrimidinyl, triazineyl; The substituents in the substituted D group are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaryl.

8. The organic electroluminescent material according to claim 7, characterized in that, The organic compound shown in formula (2) is selected from any of the structures shown in N-1 to N-348:

9. The organic electroluminescent material according to any one of claims 7 or 8, characterized in that, The mass ratio of the first main material to the second main material is 9:1 to 1:9; Preferably, the mass ratio of the first main material to the second main material is 2:8-8:2; More preferably, the mass ratio of the first main material to the second main material is 3:7-7:3; More preferably, the mass ratio of the first main material to the second main material is 4:6-6:

4.

10. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes an anode, a cathode, and an organic layer located between the anode and the cathode, wherein the organic layer includes an organic compound as described in any one of claims 1-5 or an organic electroluminescent material as described in any one of claims 6-9.

11. The organic electroluminescent device according to claim 10, characterized in that, The organic layer includes any one or a combination of at least two of the following: a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

12. The organic electroluminescent device according to claim 10 or 11, characterized in that, The organic layer includes a light-emitting layer, which comprises an organic compound as described in any one of claims 1-5 or an organic electroluminescent material as described in any one of claims 6-9.

13. The organic electroluminescent device according to claim 12, characterized in that, The light-emitting layer comprises a host material and a guest material, wherein the host material comprises an organic compound as described in any one of claims 1-5 or an organic electroluminescent material as described in any one of claims 6-9.

14. The organic electroluminescent device according to any one of claims 10-13, characterized in that, The organic layer includes a light-emitting auxiliary layer, which comprises an organic compound as described in any one of claims 1-5 or an organic electroluminescent material as described in any one of claims 6-9.

15. An electronic device, characterized in that, The electronic device includes an organic electroluminescent device as described in any one of claims 10-14, an organic compound as described in any one of claims 1-5, or an organic electroluminescent material as described in any one of claims 6-9.

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