Organic electroluminescent compound and application thereof

Abstract

The invention relates to the technical field of display, in particular to an organic electroluminescent compound and application thereof. The organic electroluminescent compound has a structure as shown in the following formula (1), substituent groups are introduced into different positions where dibenzofuran or dibenzothiophene is connected with triazine, the molecular rigidity of the compound is kept through a twisted space structure, effective accumulation beneficial to charge transfer among molecules is promoted, and the organic electroluminescent compound has the advantages that the organic electroluminescent compound has a good anti-radiation effect, and the anti-radiation performance of the compound is improved. By inhibiting the built-in electric field of the device, capacitance is reduced, intramolecular hydrogen bonds and weak interaction are balanced to improve the physical and chemical stability, so that a more stable structure can be obtained, the better thermal stability is improved, the conjugation range is expanded to a certain extent, the electron transfer balance of the device is promoted and improved, and the performance in all aspects is improved.

Description

Technical Field

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

[0002] In organic light-emitting diode (OLED) displays, the performance of green OLED pixels determines the overall brightness and lifespan of the screen. The host material of the emissive layer has a decisive influence on the performance of green OLED devices. Typically, the green emissive layer employs a dual-host design, where a P-type host with hole transport capabilities and an N-type host with electron transport capabilities together form a bipolar transport emissive layer. This dual-host design facilitates electron and hole injection and transport, reduces operating voltage, balances carrier transport, thereby protecting exciton generation efficiency and improving device luminous efficiency, suppressing various pathways leading to material degradation, and extending device lifespan. Furthermore, the N-type host material in the dual-host design not only determines electron injection and transport characteristics but also affects the device's built-in electric field, thus influencing hole injection and resulting in different capacitance characteristics. The capacitance of OLED devices is closely related to the animation effects of the display panel.

[0003] However, the structural stability of existing organic electroluminescent materials is poor, resulting in high driving voltage, low luminous efficiency, and short lifespan of organic electroluminescent devices, which seriously limits the application of organic electroluminescent diodes. Summary of the Invention

[0004] Therefore, the technical problem to be solved by the present invention is to overcome the defects of poor structural stability of existing organic electroluminescent materials, which result in high driving voltage, low luminous efficiency and short life of organic electroluminescent devices, thereby providing an organic electroluminescent compound and its application to solve the above problems.

[0005] Definitions of terms in this invention:

[0006] In this invention, "substituent" has the common meaning known in the art, referring to a chemical part that is covalently attached to or, where appropriate, fused to the parent nucleus group.

[0007] In this invention, "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 substituent Rc mentioned above 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, halogen group, cyano, alkyl, haloalkyl, trialkylsilyl, deuterated alkyl, aryl, heteroaryl, etc. Of course, the number of substituents Rc can be one or more. When two substituents Rc are attached to the same atom, the two substituents Rc can exist independently or be connected to each other to form a ring with the atom; when two adjacent substituents Rc exist on a functional group, the adjacent substituents Rc can exist independently or fuse with the functional group to which they are attached to form a ring.

[0008] In this invention, the "C1-C60, C3-C60, C6-C60" designation defines a range of carbon atoms, where the number of carbon atoms is any integer within the defined range. For example, C6-C60 aryl can represent any integer within the range of 6-60, 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, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60.

[0009] In this invention, "alkyl" refers to a saturated hydrocarbon group, whether used as part of other terms or alone, 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.

[0010] In this invention, "alkenyl" refers to a saturated hydrocarbon group, whether used as part of other terms or alone, which can be straight-chain or branched and has at least one carbon-carbon double bond. The term "C2-C60 alkenyl" refers to an alkenyl group having 2 to 60 carbon atoms, preferably 1 to 40 carbon atoms, and even more preferably 1 to 20 carbon atoms. Of course, the alkenyl group includes, but is not limited to, vinyl, n-propenyl, isopropenyl, n-butenyl, sec-butenyl, etc.

[0011] In this invention, "alkynyl" refers to a saturated alkynyl group, whether used as part of other terms or alone, which can be straight-chain or branched and has at least one carbon-carbon triple bond. The term "C2-C60 alkynyl" refers to an alkynyl group having 2 to 60 carbon atoms, preferably 2 to 40 carbon atoms, and even more preferably 2 to 20 carbon atoms. Of course, the alkynyl group includes, but is not limited to, acetylene, propyne, etc.

[0012] In this invention, "cycloalkyl" refers to a cyclic alkyl group consisting of at least 3 atoms. Further, C3-C60 cycloalkyl 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 group includes, but is not limited to, cyclopropyl, cyclobutyl, adamantyl, etc.

[0013] In this invention, "heterocyclic alkyl" includes one or more of O, S, Se, N, and Si as heteroatoms. Further, C1-C60 heterocyclic alkyl refers to a monocyclic or polycyclic ring having 1 to 60 carbon atoms, preferably 1 to 40 carbon atoms, and even more preferably 1 to 20 carbon atoms. Here, the polycyclic refers to a group in which a heterocyclic alkyl group is directly attached to or fused with another cyclic group. Here, the other cyclic group can also be a heterocyclic alkyl group, but it can also be another type of cyclic group, such as cycloalkyl, aryl, heteroaryl, etc.

[0014] In this invention, "cycloalkenyl" refers to a cyclic alkenyl group consisting of at least 3 atoms. Further, C3-C60 cycloalkenyl 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.

[0015] In this invention, "heterocyclic alkenyl" includes one or more of O, S, Se, N and Si as heteroatoms. Further, C1-C60 heterocyclic alkenyl refers to a monocyclic or polycyclic ring having 1 to 60 carbon atoms, preferably 1 to 40 carbon atoms, and even more preferably 1 to 20 carbon atoms.

[0016] In this invention, "aryl" and "arylene" include monocyclic, polycyclic, or fused-ring aryl groups. The rings can be interrupted by short non-aromatic units and may contain spiro structures. Aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, 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.

[0017] In this invention, "heteroaryl" includes monocyclic, polycyclic, or fused-ring heteroaryl groups, wherein the rings can be interrupted by short non-aromatic units, and the heteroatoms include nitrogen, oxygen, and sulfur. Heteroaryl groups include, but are not limited to, furanyl, phenylthio, pyrroloyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetraazinyl, triazolyl, tetraazolyl, furazolidyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiopheneyl, isobenzofuranyl, dibenzofuranyl, dibenzothiopheneyl, benzimidazolyl, and benzyl. Benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazoleyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxalinyl, carbazoleyl, phenoxazinyl, phenthiazinyl, phenanthidyl, benzo[m]dioxacyclopentenyl, dihydroacridyl, and their derivatives; heteroaryl groups include, but are not limited to, furanyl, phenylthio, and pyrroleyl. Imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl Azolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, ininazole, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxolinyl, carbazolyl, phenoxazinyl, phenthiazinyl, phenanthridyl, phenanthridyl, 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.

[0018] In this invention, "halogen" refers to an atom selected from fluorine, chlorine, bromine, and iodine.

[0019] Unless otherwise stated, hydrogen atoms in this invention include protium, deuterium, and tritium.

[0020] To address the existing technical problems, the present invention provides the following technical solution:

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

[0022]

[0023] Among them, X 1 and X 2Each can be independently selected from O or S;

[0024] L1 and L2 are each independently selected from single-bonded, substituted or unsubstituted C6-C60 aryl groups;

[0025] Ar 1 Ar 2 Each is independently selected from substituted or unsubstituted C6-C60 aryl groups and substituted or unsubstituted C1-C60 heteroaryl groups;

[0026] R 1 R 2 R 3 Each is independently selected from hydrogen, deuterium, halogen, hydroxyl, nitro, amidine, hydrazine, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C2-C60 alkynyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C60 heterocycloalkyl, substituted or unsubstituted C3-C60 cycloalkenyl, substituted or unsubstituted C1-C60 heterocycloalkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C1-C60 heteroaryl;

[0027] n1, n2, and n3 are each independently selected from integers from 0 to 6;

[0028] The substituents in substituted C6-C60 aryl, substituted C6-C60 aryl, substituted C1-C60 heteroaryl, substituted C1-C60 alkyl, substituted C2-C60 alkenyl, substituted C2-C60 alkynyl, substituted C3-C60 cycloalkyl, substituted C1-C60 heterocyclic alkyl, substituted C3-C60 cycloalkenyl, and substituted C1-C60 heterocyclic alkenyl are selected from deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C60 alkyl, C2-C60 alkenyl, C3-C60 cycloalkyl, C2-C60 alkynyl, C3-C60 cycloalkyl, C1-C60 heterocyclic alkyl, C3-C60 cycloalkenyl, C1-C60 heterocyclic alkenyl, C6-C60 aryl, and C1-C60 heteroaryl. Preferably, the organic electroluminescent compound has a structure as shown in any one of formulas 1-1 to 1-32:

[0029]

[0030]

[0031]

[0032]

[0033] Preferably, L1 and L2 are each independently selected from single-bonded, substituted, or unsubstituted C6-C50 arylene groups; wherein the substituents in the substituted C6-C50 arylene groups are selected from deuterium, halogen, cyano, hydroxyl, nitro, amidine, hydrazine, C1-C50 alkyl, C2-C50 alkenyl, C3-C50 cycloalkyl, C2-C50 alkynyl, C3-C50 cycloalkyl, C1-C50 heterocyclic alkyl, C3-C50 cycloalkenyl, C1-C50 heterocyclic alkenyl, and C6-C50 aryl.

[0034] Preferably, L1 and L2 are each independently selected from single-bonded, substituted, or unsubstituted C6-C30 arylene groups; wherein the substituents in the substituted C6-C30 arylene groups are selected from deuterium, halogen, cyano, hydroxyl, nitro, amidine, hydrazine, C1-C30 alkyl, C2-C30 alkenyl, C3-C30 cycloalkyl, C2-C30 alkynyl, C3-C30 cycloalkyl, C1-C30 heterocyclic alkyl, C3-C30 cycloalkenyl, C1-C30 heterocyclic alkenyl, and C6-C30 aryl.

[0035] Preferably, L1 and L2 are each independently selected from single-bonded, substituted, or unsubstituted C6-C25 arylene groups; wherein the substituents in the substituted C6-C25 arylene groups are selected from deuterium, halogen, cyano, hydroxyl, nitro, amidine, hydrazine, C1-C25 alkyl, C2-C25 alkenyl, C3-C25 cycloalkyl, C2-C25 alkynyl, C3-C25 cycloalkyl, C1-C25 heterocyclic alkyl, C3-C25 cycloalkenyl, C1-C25 heterocyclic alkenyl, and C6-C25 aryl.

[0036] More preferably, L1 and L2 are each independently selected from the group consisting of single bonds or the following groups:

[0037]

[0038] Preferably, Ar 1 Ar 2 Each is independently selected from substituted or unsubstituted C6-C50 aryl and substituted or unsubstituted C1-C50 heteroaryl groups; wherein the substituents in the substituted C6-C50 aryl and substituted C1-C50 heteroaryl groups are selected from deuterium, halogen, cyano, hydroxyl, nitro, amidine, hydrazine, C1-C50 alkyl, C2-C50 alkenyl, C3-C50 cycloalkyl, C2-C50 alkynyl, C3-C50 cycloalkyl, C1-C50 heterocycloalkyl, C3-C50 cycloalkenyl, C1-C50 heterocycloalkenyl, and C6-C50 aryl.

[0039] Preferred, Ar 1 Ar 2Each is independently selected from substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C1-C30 heteroaryl groups; wherein the substituents in the substituted C6-C30 aryl and substituted C1-C30 heteroaryl groups are selected from deuterium, halogen, cyano, hydroxyl, nitro, amidine, hydrazine, C1-C30 alkyl, C2-C30 alkenyl, C3-C30 cycloalkyl, C2-C30 alkynyl, C3-C30 cycloalkyl, C1-C30 heterocycloalkyl, C3-C30 cycloalkenyl, C1-C30 heterocycloalkenyl, and C6-C30 aryl.

[0040] Preferred, Ar 1 Ar 2 Each is independently selected from substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C1-C25 heteroaryl groups; wherein the substituents in the substituted C6-C25 aryl and substituted C1-C25 heteroaryl groups are selected from deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C25 alkyl, C2-C25 alkenyl, C3-C25 cycloalkyl, C2-C25 alkynyl, C3-C25 cycloalkyl, C1-C25 heterocycloalkyl, C3-C25 cycloalkenyl, C1-C25 heterocycloalkenyl, and C6-C25 aryl.

[0041] Preferred, Ar 1 Ar 2Each of the following is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted binaphthyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted naphthylphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenylfluorenyl, substituted or unsubstituted benzo[a]fluorenyl, substituted or unsubstituted dibenzo[a]fluorenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted benzo[a]dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted dimethylfluorenylphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted phenylphenanthryl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted indene. Substituted or unsubstituted tetraphenyl, substituted or unsubstituted peryl, substituted or unsubstituted tyl, substituted or unsubstituted condensed tetraphenyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted phenylthio, substituted or unsubstituted pyrroleyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted isothiazolyl, substituted or unsubstituted isoxazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted triazinyl, substituted or unsubstituted tetraazinyl, substituted or unsubstituted triazolyl, substituted or unsubstituted tetrazolyl, substituted or unsubstituted Substituted furazolidone, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted isobenzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dinaphthofuranyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted benzodibenzothiopheneyl, substituted or unsubstituted naphthothiopheneyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzoisothiazolyl, substituted or unsubstituted benzoisooxazolyl, substituted or unsubstituted benzooxazolyl, substituted or unsubstituted isoindolyl Substituted or unsubstituted indolyl, substituted or unsubstituted inazolyl, substituted or unsubstituted benzothiadiazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted cyclolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted carbazole, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted benzocarbazophenyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenthiazinyl, substituted or unsubstituted phenanthinyl, substituted or unsubstituted dipyridyl, substituted or unsubstituted terpyridyl, substituted or unsubstituted phenylterpyridyl, substituted or unsubstituted diazafluorenyl, or substituted or unsubstituted phenanthrolinel; wherein, Ar 1 Ar 2The substituents are selected from one or more of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, phenyl, naphthyl, biphenyl, binatyl, bitriphenyl, fluorenyl, dibenzofuranyl, dibenzothiophene, or carbazole.

[0042] Preferred, Ar 1 Ar 2 Each is independently selected from the group consisting of the following groups:

[0043]

[0044]

[0045] Preferably, R 1 R 2 R 3 Each is independently selected from hydrogen, deuterium, halogen, hydroxyl, nitro, amidine, hydrazine, substituted or unsubstituted C1-C50 alkyl, substituted or unsubstituted C2-C50 alkenyl, substituted or unsubstituted C2-C50 alkynyl, substituted or unsubstituted C3-C50 cycloalkyl, substituted or unsubstituted C1-C50 heterocycloalkyl, substituted or unsubstituted C3-C50 cycloalkenyl, substituted or unsubstituted C1-C50 heterocycloalkenyl, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C1-C50 heteroaryl; wherein, R 1 R 2 R 3 The substituents are each independently selected from deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C50 alkyl, C2-C50 alkenyl, C3-C50 cycloalkyl, C2-C50 alkynyl, C3-C50 cycloalkyl, C1-C50 heterocyclic alkyl, C3-C50 cycloalkenyl, C1-C50 heterocyclic alkenyl, and C6-C50 aryl;

[0046] Preferred, R 1 R 2 R 3Each is independently selected from hydrogen, deuterium, halogen, hydroxyl, nitro, amidine, hydrazine, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C2-C25 alkynyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C3-C25 cycloalkenyl, substituted or unsubstituted C1-C25 heterocyclic alkenyl, substituted or unsubstituted C6 -C25 aryl, substituted or unsubstituted C1-C25 heteroaryl; wherein the substituents of R1, R2, and R3 are each independently selected from deuterium, halogen, cyano, hydroxyl, nitro, amidine, hydrazine, C1-C25 alkyl, C2-C25 alkenyl, C3-C25 cycloalkyl, C2-C25 alkynyl, C3-C25 cycloalkyl, C1-C25 heterocycloalkyl, C3-C25 cycloalkenyl, C1-C25 heterocycloalkenyl, and C6-C25 aryl;

[0047] Preferred, R 1 R 2 R 3 Each is independently selected from the group consisting of hydrogen, deuterium, or the following groups:

[0048]

[0049] Preferably, n1, n2, and n3 are each independently selected from integers from 0 to 5;

[0050] Preferably, n1, n2, and n3 are each independently selected from integers from 0 to 2.

[0051] Preferably, the electroluminescent compound has any one of the structures shown in G-1 to G-224:

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064] Secondly, the present invention provides a method for synthesizing the above-mentioned organic electroluminescent compound, the synthetic route of which is shown in reaction formula 1:

[0065]

[0066] In reaction formula 1, the compounds of this invention are synthesized using the Suzuki coupling method. Specifically, a disubstituted dibenzofuran (thiophene) borate ester derivative is coupled with a triphenyl-substituted halogenated triazine derivative in the presence of a zero-valent palladium catalyst to form the target product. The product is generally purified by silica gel column chromatography and solvent recrystallization; before device fabrication, the product is further purified by vacuum thermal sublimation.

[0067] Thirdly, the present invention provides an organic electroluminescent material comprising the above-mentioned organic electroluminescent compound.

[0068] Fourthly, the present invention provides an organic electroluminescent device, the organic electroluminescent device comprising a first electrode, a second electrode disposed opposite to the first electrode, and at least one organic layer disposed between the first electrode and the second electrode, the organic layer comprising the aforementioned organic electroluminescent material.

[0069] The organic layer is composed of a single-layer structure or a multilayer structure consisting of two or more layers. For example, the organic electroluminescent device includes one or more of the following sequentially arranged elements: a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer. It should be noted that if an electron blocking layer and a hole blocking layer are present, the aforementioned organic electroluminescent compound or organic electroluminescent material is located between the electron blocking layer and the hole blocking layer, i.e., it belongs to the light-emitting layer material.

[0070] The anode material is a material with a large work function that facilitates hole injection into the hole transport layer. Examples of anode materials include, but are not limited to: 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).

[0071] The hole injection layer enhances the ability to inject holes into the hole transport layer. The hole injection layer can be selected from benzidine derivatives, starburst-like aryl amine compounds, phthalocyanine derivatives, or other materials; this 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:

[0072]

[0073]

[0074] The hole transport layer may include one or more hole transport materials. The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. The material of the hole transport layer may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. This application does not impose any special limitations on this. For example, the material of the hole transport layer may be selected from the following compounds or any combination thereof:

[0075]

[0076] The material of the electron blocking layer is selected from conventional materials used in the art. An electron blocking layer is a layer disposed between the light-emitting auxiliary layer and the light-emitting layer to prevent electrons injected from the cathode from transferring to the light-emitting auxiliary layer and recombinating in the light-emitting layer; it can also be called an electron blocking layer or an electron suppression layer. Preferably, the electron blocking layer is made of a material with a lower electron affinity than the electron transport layer. This application does not impose any special limitations in this regard.

[0077] The luminescent layer is a substance that can receive holes and electrons from the hole transport layer and the electron transport layer respectively, and combine them to emit light in the visible light region.

[0078] The hole blocking layer is made of a material conventionally used in the art. It is a layer disposed between the electron transport layer and the light-emitting layer to prevent holes injected from the anode from being transferred to the electron transport layer and recombinating in the light-emitting layer; it can also be called a hole suppression layer or a hole blocking layer. Preferably, the hole blocking layer is made of a material with high ionization energy. This application does not impose any special limitations in this regard.

[0079] The electron transport layer can be a single-layer or multi-layer structure, and may include one or more electron transport materials. The electron transport layer receives electrons from the cathode or an electron injection layer formed on the cathode, transports electrons to the light-emitting layer, and suppresses hole transfer from the light-emitting layer. The electron transport material is suitably one that can effectively receive electron injection from the cathode and transfer electrons to the light-emitting layer, and has a high electron mobility. The electron transport layer may be selected from, but is not limited to, Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavonoid-metal complexes, etc., but is not limited to these. The electron transport layer includes, but is not limited to, the following structures:

[0080]

[0081] The electron injection layer is used to enhance the ability to inject electrons into the electron transport layer. The electron injection layer may include fluorenone, anthraquinone dimethane, biphenylquinone, thiamethane dioxide, azole, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenemethane, anthrone, and their derivatives; inorganic materials such as alkali metal sulfides and alkali metal halides; or may include complexes of alkali metals and organic compounds.

[0082] The cathode is a material with a small work function that 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.

[0083] Fifthly, the present invention also provides an application of the above-mentioned 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.

[0084] The technical solution of this invention has the following advantages:

[0085] The organic electroluminescent compound of the present invention has a structure as shown in formula (1). By introducing substituents at different positions where dibenzofuran or dibenzothiophene is connected to triazine, the twisted spatial structure maintains the rigidity of the compound molecule, promotes effective stacking between molecules that is conducive to charge transport, reduces capacitance by suppressing the built-in electric field of the device, and balances intramolecular hydrogen bonds and weak interactions to improve physicochemical stability. Thus, a more stable structure can be obtained, thereby improving thermal stability and expanding the conjugation range to a certain extent, promoting the improvement of the electronic transport balance of the device and improving the performance in all aspects. Attached Figure Description

[0086] 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.

[0087] Figure 1 This is a schematic diagram of the structure of the organic electroluminescent device in an embodiment of the present invention;

[0088] Explanation of reference numerals in the attached figures: 1-substrate; 2-anode; 3-hole injection layer; 4-hole transport layer; 5-electron blocking layer; 6-light emitting layer; 7-hole blocking layer; 8-electron transport layer; 9-electron injection layer; 10-cathode. Detailed Implementation

[0089] 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.

[0090] 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.

[0091] Synthesis of raw material G70-A:

[0092]

[0093] Synthetic intermediate G70-A-1

[0094] Compound G70-AA (54 mmol, 20.0 g), 2-bromo-3-chloronaphthalene (G70-AB) (71436-67-4, 56 mmol, 13.7 g), Pd(PPh3)4 (0.4 mmol, 0.50 g), and K2CO3 (108 mmol, 14.9 g) were reacted in a mixed solution of toluene (160 mL) and water (40 mL) under a nitrogen atmosphere at 95 °C for 4 h. After the reaction was complete, the mixture was cooled to room temperature, separated, extracted with water and ethyl acetate, concentrated by rotary evaporation, and purified by column chromatography to give a white solid G70-A-1 (20.1 g, 92% yield).

[0095] Synthetic intermediate G70-A

[0096] G70-A-1 (50 mmol, 20.0 g), pinacol diborate (59 mmol, 15.1 g), Pd(dppf)Cl2 (0.4 mmol, 0.29 g), and potassium acetate (99 mmol, 9.7 g) were weighed into glass flasks. Under nitrogen protection, 200 mL of ultra-dry dioxane was added, and the reaction was heated to 100 °C and stirred for 3 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the solvent was removed by rotary evaporation of the filtrate. The filtrate was then purified by column chromatography to obtain a white solid G70-A (21.6 g, yield 88%).

[0097] G96-A, G182-A, G195-A, and G206-A were prepared using the same synthesis method as raw material G70-A. The specific raw material substitutions and yields are shown in Table 1 below.

[0098] Table 1

[0099]

[0100] Example 1

[0101] This embodiment provides a method for preparing an organic electroluminescent compound with a G-1 structure, the synthesis steps of which are shown below:

[0102]

[0103] Synthetic intermediate G1-1:

[0104] Compounds G1-A (2324189-09-3, 45 mmol, 20.0 g), 2,4-dichloro-6-phenyl-1,3,5-triazine (G1-B) (90 mmol, 20.3 g), Pd(dppf)Cl2 (0.36 mmol, 0.26 g), and K2CO3 (54 mmol, 7.4 g) were weighed into a 500 mL three-necked flask. Dioxane (160 mL) and water (40 mL) were added, and the mixture was purged with nitrogen and stirred at 80 °C for 12 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered with water, dissolved in toluene, and filtered through a silica gel column. The filtrate was evaporated by rotary evaporation to remove the solvent. The crude product was recrystallized from tetrahydrofuran to obtain a white solid G1-1 (16.4 g, 72% yield).

[0105] Synthesized compound G1:

[0106] Under nitrogen protection, G1-1 (20 mmol, 10.0 g), G1-C (21 mmol, 7.9 g), Pd(PPh3)4 (0.16 mmol, 0.18 g), and K2CO3 (39 mmol, 5.4 g) were heated under reflux at 100 °C overnight in a mixture of dioxane (80 mL) and water (20 mL). After the reaction was complete, the mixture was cooled to room temperature and filtered with water. The filter cake was dissolved in toluene and filtered through a silica gel column. The filtrate was evaporated by rotary evaporation to remove the solvent. The crude product was recrystallized from toluene to obtain product G-1 as a white solid, 12.4 g, with a yield of 86%.

[0107] Elemental analysis: C 51 H 31 N3OS. Theoretical values: C, 83.47; H, 4.26; N, 5.73; O, 2.18; S, 4.37; Measured values: C, 83.46; H, 4.25; N, 5.72; S, 4.37;

[0108] HRMS(ESI)m / z[M+H] + Theoretical value: 733.22; Measured value: 734.19.

[0109] Example 2

[0110] Compound G-6 was prepared using the same synthetic method as in Example 1, except that starting material G6-A was used instead of G1-A and starting material G6-C was used instead of G1-C. The synthetic route is shown below:

[0111]

[0112] Compound G-6 was obtained in 80% yield. Elemental analysis: C 51 H 31 N3OS. Theoretical values: C, 83.47; H, 4.26; N, 5.73; O, 2.18; S, 4.37; Measured values: C, 83.47; H, 4.24; N, 5.72; S, 4.38;

[0113] HRMS(ESI)m / z[M+H] + Theoretical value: 733.22; Measured value: 734.21.

[0114] Example 3

[0115] Compound G-10 was prepared using the same synthetic method as in Example 1, except that starting material G6-A was used instead of G1-1 and starting material G10-C was used instead of G1-C. The synthetic route is shown below:

[0116]

[0117] Compound G-10 was obtained in 81% yield. Elemental analysis: C 51 H 31 N3OS. Theoretical values: C, 83.47; H, 4.26; N, 5.73; O, 2.18; S, 4.37; Measured values: C, 83.45; H, 4.25; N, 5.73; S, 4.35;

[0118] HRMS(ESI)m / z[M+H]+: Theoretical value: 733.22; Measured value: 734.22.

[0119] Example 4

[0120] Compound G-70 was prepared using the same synthetic method as in Example 1, except that starting material G70-A was used instead of G1-A and starting material G6-C was used instead of G1-C. The synthetic route is shown below:

[0121]

[0122] Compound G-70 was obtained. Elemental analysis: C 55 H 33 N3OS. Theoretical values: C, 84.27; H, 4.24; N, 5.36; O, 2.04; S, 4.09; Measured values: C, 84.26; H, 4.25; N, 5.36; S, 4.07;

[0123] HRMS(ESI)m / z[M+H]+: Theoretical value: 783.23; Measured value: 784.22.

[0124] Example 5

[0125] Compound G-79 was prepared using the same synthetic method as in Example 1, except that starting material G79-A was used instead of G1-A and G79-C was used instead of G1-C. The synthetic route is shown below:

[0126]

[0127] Compound G-79 was obtained in 81% yield. Elemental analysis: C 57 H 35 N3OS. Theoretical values: C, 84.52; H, 4.36; N, 5.19; O, 1.98; S, 3.96; Measured values: C, 84.51; H, 4.34; N, 5.17; S, 3.94;

[0128] HRMS(ESI)m / z[M+H]+: Theoretical value: 809.25; Measured value: 810.22.

[0129] Example 6

[0130] Compound G-88 was prepared using the same synthetic method as in Example 1, except that starting materials G88-A were used instead of G1-A, G88-B instead of G1-B, and G70-C instead of G1-C. The synthetic route is shown below:

[0131]

[0132] Compound G-88 was obtained in 84% yield. Elemental analysis: C 55 H 33 N3OS. Theoretical values: C, 84.27; H, 4.24; N, 5.36; O, 2.04; S, 4.09; Measured values: C, 84.25; H, 4.22; N, 5.35; S, 4.10;

[0133] HRMS(ESI)m / z[M+H]+: Theoretical value: 783.23; Measured value: 784.21.

[0134] Example 7

[0135] Compound G-96 was prepared using the same synthetic method as in Example 1, except that starting material G96-A was used instead of G1-A and G79-C was used instead of G96-C. The synthetic route is shown below:

[0136]

[0137] Compound G-96 was obtained in 79% yield. Elemental analysis: C 59 H 35 N3OS. Theoretical values: C, 84.97; H, 4.23; N, 5.04; O, 1.92; S, 3.84; Measured values: C, 84.95; H, 4.22; N, 5.04; S, 3.82;

[0138] HRMS(ESI)m / z[M+H]+: Theoretical value: 833.25; Measured value: 834.22.

[0139] Example 8

[0140] Compound G-130 was prepared using the same synthetic method as in Example 1, except that starting material G130-A was used instead of G1-A and G130-C was used instead of G1-C. The synthetic route is shown below:

[0141]

[0142] Compound G-130 was obtained in 78% yield. Elemental analysis: C 51 H 31N3OS. Theoretical values: C, 83.47; H, 4.26; N, 5.73; O, 2.18; S, 4.37; Measured values: C, 83.45; H, 4.24; N, 5.71; S, 4.39;

[0143] HRMS(ESI)m / z[M+H]+: Theoretical value: 733.22; Measured value: 734.21.

[0144] Example 9

[0145] Compound G-136 was prepared using the same synthetic method as in Example 1, except that starting material G136-A was used instead of G1-A and G136-C was used instead of G1-C. The synthetic route is shown below:

[0146]

[0147] Compound G-136 was obtained in 77% yield. Elemental analysis: C 51 H 31 N3OS. Theoretical values: C, 83.47; H, 4.26; N, 5.73; O, 2.18; S, 4.37; Measured values: C, 83.47; H, 4.25; N, 5.74; S, 4.36;

[0148] HRMS(ESI)m / z[M+H]+: Theoretical value: 733.22; Measured value: 734.23.

[0149] Example 10

[0150] Compound G-182 was prepared using the same synthetic method as in Example 1, except that starting material G182-A was used instead of G1-A and G182-C was used instead of G1-C. The synthetic route is shown below:

[0151]

[0152] Compound G-182 was obtained in 79% yield. Elemental analysis: C 55 H 33 N3OS. Theoretical values: C, 84.27; H, 4.24; N, 5.36; O, 2.04; S, 4.09; Measured values: C, 84.29; H, 4.24; N, 5.34; S, 4.08;

[0153] HRMS(ESI)m / z[M+H]+: Theoretical value: 783.23; Measured value: 784.19.

[0154] Example 11

[0155] Compound G-195 was prepared using the same synthetic method as in Example 1, except that starting material G195-A was used instead of G1-A and G195-C was used instead of G1-C. The synthetic route is shown below:

[0156]

[0157] Compound G-195 was obtained in 79% yield. Elemental analysis: C 63 H 39 N3OS. Theoretical values: C, 85.40; H, 4.44; N, 4.74; O, 1.81; S, 3.62; Measured values: C, 85.41; H, 4.43; N, 4.73; S, 3.60;

[0158] HRMS(ESI)m / z[M+H]+: Theoretical value: 885.28; Measured value: 886.29.

[0159] Example 12

[0160] Compound G-195 was prepared using the same synthetic method as in Example 1, except that starting material G206-A was used instead of G1-A and G206-C was used instead of G1-C. The synthetic route is shown below:

[0161]

[0162] Compound G-206 was obtained in 77% yield. Elemental analysis: C 59 H 35 N3OS. Theoretical values: C, 84.97; H, 4.23; N, 5.04; O, 1.92; S, 3.84; Measured values: C, 84.976; H, 4.22; N, 5.03; S, 3.81;

[0163] HRMS(ESI)m / z[M+H]+: Theoretical value: 833.25; Measured value: 833.26.

[0164] Device Examples

[0165] The materials used to prepare the following device embodiments or device comparative examples are shown in Table 2 below.

[0166] Table 2

[0167]

[0168] Device Example 1

[0169] This embodiment provides an organic electroluminescent device, such as... Figure 1As shown, the device includes an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode 10, which are sequentially stacked on a substrate 1. The device structure is: anode (indium tin oxide (ITO) coated glass substrate) / hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL) / light-emitting layer (EML) / hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) / cathode (Al).

[0170] The specific fabrication process of the above-mentioned organic electroluminescent device is as follows:

[0171] 1) Substrate cleaning:

[0172] 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.

[0173] 2) Preparation of organic layer:

[0174] 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) / hole transport layer (HTL) / electron blocking layer (EBL) / light emitting layer (EML) / hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) / thick cathode (Al) are sequentially deposited on the anode film.

[0175] in:

[0176] The hole injection layer (HIL) is made of HI-1, has a thickness of 10 nm, and a total evaporation rate of 0.1 nm / s.

[0177] The hole transport layer (HTL) is made of HT-1 material, has a thickness of 100 nm, and a total evaporation rate of 0.1 nm / s.

[0178] The electron blocking layer (EBL) is made of EB-1, has a thickness of 5 nm, and a total evaporation rate of 0.1 nm / s.

[0179] The light-emitting layer (EML) is vacuum-deposited by co-evaporation. The material of the light-emitting layer includes a host material and a guest material. The guest material is GD-1, and the host material is composed of G-1 compound and GHP-1 compound from Example 1. The specific ratio of the host material and the guest material is shown in Table 3 below. The thickness is 30 nm, and the total evaporation rate is 0.1 nm / s.

[0180] The hole blocking layer (HBL) is made of HB-1 with a thickness of 5 nm and a total evaporation rate of 0.1 nm / s.

[0181] The electron transport layer (ETL) is a binary mixture of ET-1 and LiQ in a mass ratio of 1:1, with a thickness of 30 nm and a total evaporation rate of 0.1 nm / s.

[0182] The electron injection layer (EIL) is made of LiF with a thickness of 1 nm and a total evaporation rate of 0.1 nm / s.

[0183] The cathode is made of aluminum with a thickness of 100 nm and a deposition rate of 1 nm / s.

[0184] Device Example 2

[0185] The difference between this device embodiment and device embodiment 1 is that material G-1 is replaced with G-6 in embodiment 2. The specific ratio of the main material and the guest material is shown in Table 3 below. Other conditions are the same as those in device embodiment 1.

[0186] Device Example 3

[0187] The difference between this device embodiment and device embodiment 1 is that material G-1 is replaced with G-10 in embodiment 3. The specific ratio of the main material and the guest material is shown in Table 3 below. Other conditions are the same as those in device embodiment 1.

[0188] Device Example 4

[0189] The difference between this device embodiment and device embodiment 1 is that material G-1 is replaced with G-70 in embodiment 4. The specific ratio of the main material and the guest material is shown in Table 3 below. Other conditions are the same as those in device embodiment 1.

[0190] Device Example 5

[0191] The difference between this device embodiment and device embodiment 1 is that material G-1 is replaced with G-79 in embodiment 5. The specific ratio of the main material and the guest material is shown in Table 3 below. Other conditions are the same as those in device embodiment 1.

[0192] Device Example 6

[0193] The difference between this device embodiment and device embodiment 1 is that material G-1 is replaced with G-88 in embodiment 6. The specific ratio of the main material and the guest material is shown in Table 3 below. Other conditions are the same as those in device embodiment 1.

[0194] Device Example 7

[0195] The difference between this device embodiment and device embodiment 1 is that material G-1 is replaced with G-96 in embodiment 7. The specific ratio of the main material and the guest material is shown in Table 3 below. Other conditions are the same as those in device embodiment 1.

[0196] Device Example 8

[0197] The difference between this device embodiment and device embodiment 1 is that material G-1 is replaced with G-130 in embodiment 8. The specific ratio of the main material and the guest material is shown in Table 3 below. Other conditions are the same as those in device embodiment 1.

[0198] Device Example 9

[0199] The difference between this device embodiment and device embodiment 1 is that material G-1 is replaced with G-136 in embodiment 9. The specific ratio of the main material and the guest material is shown in Table 3 below. Other conditions are the same as those in device embodiment 1.

[0200] Device Example 10

[0201] The difference between this device embodiment and device embodiment 1 is that material G-1 is replaced with G-182 in embodiment 10. The specific ratio of the main material and the guest material is shown in Table 3 below. Other conditions are the same as those in device embodiment 1.

[0202] Device Example 11

[0203] The difference between this device embodiment and device embodiment 1 is that material G-1 is replaced with G-195 in embodiment 11. The specific ratio of the main material and the guest material is shown in Table 3 below. Other conditions are the same as those in device embodiment 1.

[0204] Device Example 12

[0205] The difference between this device embodiment and device embodiment 1 is that material G-1 is replaced with G-206 in embodiment 12. The specific ratio of the main material and the guest material is shown in Table 3 below. Other conditions are the same as those in device embodiment 1.

[0206] Device Comparison Example 1

[0207] The difference between this device and device embodiment 1 is that material G-1 is changed to the REF-1 structure shown below. The specific ratio of the main material and the guest material is shown in Table 3 below. Other conditions are the same as those in device embodiment 1.

[0208]

[0209] Device Comparison Example 2

[0210] The difference between this device and device embodiment 1 is that material G-1 is changed to the REF-2 structure shown below. The specific ratio of the main material and the guest material is shown in Table 3 below. Other conditions are the same as those in device embodiment 1.

[0211]

[0212] Device Comparison Example 3

[0213] The difference between this device and device embodiment 1 is that material G-1 is changed to the REF-3 structure shown below. The specific ratio of the main material and the guest material is shown in Table 3 below. Other conditions are the same as in embodiment 1.

[0214]

[0215] Compound REF-3 was prepared as described in Example 1, except that G1-C was replaced by REF3-C. The specific structure of REF3-C is shown below:

[0216]

[0217] Compound REF-3 was obtained in 76% yield. Elemental analysis: C 45 H 27 N3OS; Theoretical values: C, 82.17; H, 4.14; N, 6.39; O, 2.43; S, 4.87; Measured values: C, 82.19; H, 4.15; N, 6.35; S: 4.86.

[0218] HRMS(ESI)m / z[M+H] + Theoretical value: 657.17; Measured value: 658.12.

[0219] Device Comparison Example 4

[0220] The difference between this device and device embodiment 1 is that material G-1 is changed to the REF-4 structure shown below. The specific ratio of the main material and the guest material is shown in Table 3 below. Other conditions are the same as in embodiment 1.

[0221]

[0222] Compound REF-4 was prepared as described in Example 1, except that G1-C was replaced by REF4-C. The specific structure of REF4-C is shown below:

[0223]

[0224] Compound REF-4 was obtained in 75% yield. Elemental analysis: C 51 H 31 N3OS; Theoretical values: C, 83.47; H, 4.26; N, 5.73; O, 2.18; S, 4.37; Measured values: C, 83.48; H, 4.28; N, 5.67; S: 4.39.

[0225] HRMS(ESI)m / z[M+H] + Theoretical value: 733.22; Measured value: 733.33.

[0226] Table 3

[0227] Serial Number EML / Thickness Device Example 1 G-1:GHP-1:GD-1 (mass ratio 45:45:10) / 30nm Device Example 2 G-6:GHP-1:GD-1 (mass ratio 45:45:10) / 30nm Device Example 3 G-10:GHP-1:GD-1 (mass ratio 45:45:10) / 30nm Device Example 4 G-70:GHP-1:GD-1 (mass ratio 45:45:10) / 30nm Device Example 5 G-79:GHP-1:GD-1 (mass ratio 45:45:10) / 30nm Device Example 6 G-88:GHP-1:GD-1 (mass ratio 45:45:10) / 30nm Device Example 7 G-96:GHP-1:GD-1 (mass ratio 45:45:10) / 30nm Device Example 8 G-130:GHP-1:GD-1 (mass ratio 45:45:10) / 30nm Device Example 9 G-136:GHP-1:GD-1 (mass ratio 45:45:10) / 30nm Device Example 10 G-182:GHP-1:GD-1 (mass ratio 45:45:10) / 30nm Device Example 11 G-195:GHP-1:GD-1 (mass ratio 45:45:10) / 30nm Device Example 12 G-206:GHP-1:GD-1 (mass ratio 45:45:10) / 30nm Device Comparison Example 1 REF-1:GHP-1:GD-1 (mass ratio 45:45:10) / 30nm Device Comparison Example 2 REF-2:GHP-1:GD-1 (mass ratio 45:45:10) / 30nm Device Comparison Example 3 REF-3:GHP-1:GD-1 (mass ratio 45:45:10) / 30nm Device Comparison Example 4 REF-4:GHP-1:GD-1 (mass ratio 45:45:10) / 30nm

[0228] Test case

[0229] The organic electroluminescent devices obtained in Device Examples 1-12 and Device Comparative Examples 1-4 in the device examples were tested.

[0230] Instruments: The current, voltage, brightness, emission spectrum and other characteristics of the device were tested simultaneously using a PR 650 spectral scanning luminance meter and a Keithley K 2400 digital source meter system;

[0231] Test conditions: Photoelectric property test conditions: current density 10 mA / cm² 2 .

[0232] Lifetime test: Current density 80mA / cm 2 The time (in hours) when the device brightness drops to 95% of its original brightness is recorded. The lifetime T95 of device comparative example 1 is set to 100, and the lifetimes of other devices are relative values ​​to the lifetimes of device comparative example 1.

[0233] The device performance test results are shown in Table 4:

[0234] Table 4

[0235]

[0236]

[0237] As can be seen from Device Examples 1 to 12 and Device Comparative Examples 1 to 4, the organic electroluminescent compounds prepared by the present invention, when applied to organic electroluminescent devices, significantly improve the lifespan of the organic electroluminescent devices, and also result in lower driving voltage and higher luminous efficiency.

[0238] 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 by The organic electroluminescent compound has a structure shown in formula (1): wherein X 1 and X 2 are each independently selected from O or S; L1, L2are each independently selected from a single bond, substituted or unsubstituted C6-C60arylene; Ar 1 , Ar 2 each independently is selected from substituted or unsubstituted C6-C60aryl, substituted or unsubstituted C1-C60heteroaryl; R 1 , R 2 , R 3 each independently is selected from hydrogen, deuterium, halogen, hydroxyl, nitro, amidine, hydrazine, substituted or unsubstituted C1-C60alkyl, substituted or unsubstituted C2-C60alkenyl, substituted or unsubstituted C2-C60alkynyl, substituted or unsubstituted C3-C60cycloalkyl, substituted or unsubstituted C1-C60heterocycloalkyl, substituted or unsubstituted C3-C60cycloalkenyl, substituted or unsubstituted C1-C60heterocycloalkenyl, substituted or unsubstituted C6-C60aryl, substituted or unsubstituted C1-C60heteroaryl; n1, n2, n3are each independently selected from an integer from 0 to 6; The substituents in the substituted C6-C60arylene, the substituted C6-C60aryl, the substituted C1-C60heteroaryl, the substituted C1-C60alkyl, the substituted C2-C60alkenyl, the substituted C2-C60alkynyl, the substituted C3-C60cycloalkyl, the substituted C1-C60heterocycloalkyl, the substituted C3-C60cycloalkenyl, the substituted C1-C60heterocycloalkenyl are selected from deuterium, halogen, cyano, hydroxyl, nitro, amidino, hydrazine, C1-C60alkyl, C2-C60alkenyl, C3-C60cycloalkyl, C2-C60alkynyl, C3-C60cycloalkyl, C1-C60heterocycloalkyl, C3-C60cycloalkenyl, C1-C60heterocycloalkenyl, C6-C60aryl, C1-C60heteroaryl.

2. The organic electroluminescence compound according to claim 1, wherein The organic electroluminescent compound has a structure shown in any one of the following formulae 1-1 to 1-32:

3. The organic electroluminescence compound according to claim 1 or 2, wherein L1, L2are each independently selected from a single bond, substituted or unsubstituted C6-C50arylene; wherein the substituents in the substituted C6-C50arylene are selected from deuterium, halogen, cyano, hydroxyl, nitro, amidino, hydrazine, C1-C50alkyl, C2-C50alkenyl, C3-C50cycloalkyl, C2-C50alkynyl, C3-C50cycloalkyl, C1-C50heterocycloalkyl, C3-C50cycloalkenyl, C1-C50heterocycloalkenyl, C6-C50aryl; Preferably, L1, L2are each independently selected from a single bond, substituted or unsubstituted C6-C25arylene; wherein the substituents in the substituted C6-C25arylene are selected from deuterium, halogen, cyano, hydroxyl, nitro, amidino, hydrazine, C1-C25alkyl, C2-C25alkenyl, C3-C25cycloalkyl, C2-C25alkynyl, C3-C25cycloalkyl, C1-C25heterocycloalkyl, C3-C25cycloalkenyl, C1-C25heterocycloalkenyl, C6-C25aryl; More preferably, L1, L2are each independently selected from a single bond or the following group consisting of:

4. The organic electroluminescence compound according to any one of claims 1 to 3, characterized by Ar 1 , Ar 2 each independently is selected from the group consisting of substituted or unsubstituted C6-C50aryl, substituted or unsubstituted C1-C50heteroaryl; wherein the substituents of the substituted C6-C50aryl, substituted C1-C50heteroaryl are selected from the group consisting of deuterium, halogen, cyano, hydroxyl, nitro, amidino, hydrazino, C1-C50alkyl, C2-C50alkenyl, C3-C50cycloalkyl, C2-C50alkynyl, C3-C50cycloalkyl, C1-C50heterocycloalkyl, C3-C50cycloalkenyl, C1-C50heterocycloalkenyl, C6-C50aryl; Preferably, Ar 1 , Ar 2 each independently is selected from the group consisting of substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C1-C30heteroaryl; wherein the substituents of the substituted C6-C30aryl, substituted C1-C30heteroaryl are selected from the group consisting of deuterium, halogen, cyano, hydroxyl, nitro, amidino, hydrazino, C1-C30alkyl, C2-C30alkenyl, C3-C30cycloalkyl, C2-C30alkynyl, C3-C30cycloalkyl, C1-C30heterocycloalkyl, C3-C30cycloalkenyl, C1-C30heterocycloalkenyl, C6-C30aryl; Preferably, Ar 1 , Ar 2 each independently is selected from the group consisting of substituted or unsubstituted C6-C25aryl, substituted or unsubstituted C1-C25heteroaryl; wherein the substituents of the substituted C6-C25aryl, substituted C1-C25heteroaryl are selected from the group consisting of deuterium, halogen, cyano, hydroxyl, nitro, amidino, hydrazino, C1-C25alkyl, C2-C25alkenyl, C3-C25cycloalkyl, C2-C25alkynyl, C3-C25cycloalkyl, C1-C25heterocycloalkyl, C3-C25cycloalkenyl, C1-C25heterocycloalkenyl, C6-C25aryl; Preferably, Ar 1 , Ar 2 each independently is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted binaphthyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted naphthylphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenylfluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted dibenzofluorenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted benzdifluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dimethylfluorenylphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted phenylphenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted indenyl, substituted or unsubstituted naphthacenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted tetracenyl, substituted or unsubstituted chrysene, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted isothiazolyl, substituted or unsubstituted isoxazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted triazinyl, substituted or unsubstituted tetrazinyl, substituted or unsubstituted triazolyl, substituted or unsubstituted tetrazolyl, substituted or unsubstituted furazanyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted isobenzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dinaphthofuranyl, substituted or unsubstituted benzdinaphthofuranyl, substituted or unsubstituted benzdibenzofuranyl, substituted or unsubstituted naphthothiophenyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzoisothiazolyl, substituted or unsubstituted benzoisoxazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted isoindolyl, substituted or unsubstituted indolyl, substituted or unsubstituted indazolyl, substituted or unsubstituted benzothiadiazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted cinnolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted benzocarbazolophenyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenanthridinyl, substituted or unsubstituted bipyridinyl, substituted or unsubstituted terpyridinyl, substituted or unsubstituted phenylterpyridinyl, substituted or unsubstituted dibenzofluorenyl, or substituted or unsubstituted phenanthrolinyl; wherein, Ar 1 , Ar 2 substituents are selected from one or more of deuterium, halogen, cyano, hydroxyl, nitro, amidino, hydrazino, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, naphthyl, biphenyl, binaphthyl, bitriphenyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl; Preferably, Ar 1 , Ar 2 each independently is selected from the group consisting of 5. The organic electroluminescence compound according to any one of claims 1 to 4, characterized by R 1 , R 2 , R 3 are each independently selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, nitro, amidino, hydrazino, substituted or unsubstituted C1-C50alkyl, substituted or unsubstituted C2-C50alkenyl, substituted or unsubstituted C2-C50alkynyl, substituted or unsubstituted C3-C50cycloalkyl, substituted or unsubstituted C1-C50heterocycloalkyl, substituted or unsubstituted C3-C50cycloalkenyl, substituted or unsubstituted C1-C50heterocycloalkenyl, substituted or unsubstituted C6-C50aryl, substituted or unsubstituted C1-C50heteroaryl; wherein the substituents of the substituted R 1 , R 2 , R 3 are each independently selected from the group consisting of deuterium, halogen, cyano, hydroxyl, nitro, amidino, hydrazino, C1-C50alkyl, C2-C50alkenyl, C3-C50cycloalkyl, C2-C50alkynyl, C3-C50cycloalkyl, C1-C50heterocycloalkyl, C3-C50cycloalkenyl, C1-C50heterocycloalkenyl, C6-C50aryl. Preferred, R 1 R 2 R 3 Each is independently selected from hydrogen, deuterium, halogen, hydroxyl, nitro, amidine, hydrazine, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C2-C25 alkynyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C3-C25 cycloalkenyl, substituted or unsubstituted C1-C25 heterocyclic alkenyl, substituted or unsubstituted C6 -C25 aryl, substituted or unsubstituted C1-C25 heteroaryl; wherein the substituents of R1, R2, and R3 are each independently selected from deuterium, halogen, cyano, hydroxyl, nitro, amidine, hydrazine, C1-C25 alkyl, C2-C25 alkenyl, C3-C25 cycloalkyl, C2-C25 alkynyl, C3-C25 cycloalkyl, C1-C25 heterocycloalkyl, C3-C25 cycloalkenyl, C1-C25 heterocycloalkenyl, and C6-C25 aryl; R 1 , R 2 , R 3 are each independently selected from the group consisting of hydrogen, deuterium or the following group of radicals:

6. The organic electroluminescence compound according to any one of claims 1 to 5, characterized by n1, n2, n3are each independently selected from an integer from 0 to 5; Preferably, n1, n2, n3are each independently selected from an integer from 0 to 2.

7. The organic electroluminescence compound according to any one of claims 1 to 6, characterized by The organic electroluminescent compound has a structure shown in any one of the following G-1 to G-224:

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

9. An organic electroluminescent device, characterized by The organic electroluminescent device comprises a first electrode, a second electrode disposed opposite to the first electrode, and at least one organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises the organic electroluminescent material according to claim 8.

10. Use of the organic electroluminescent device according to claim 9 in an optical fiber device, a lighting device, an electrophotographic photoreceptor device, a photoelectric converter, an organic solar cell, a switching element device, an organic light emitting field effect transistor, an image sensor, or a dye laser.

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