Anthracene derivative containing multiple boron atoms and its application

Abstract

The present invention relates to an anthracene derivative containing multiple boron atoms, an organic electroluminescent material, a light-emitting device, and a consumer product. The anthracene derivative of the present invention comprises a novel organic electroluminescent compound having a macrocyclic planar structure formed by anthracene and a seven-membered ring. The seven-membered ring anthracene derivative achieves HOMO and LUMO separation through the resonance effect between boron and nitrogen, thereby realizing the TADF effect and achieving a shorter emission wavelength compared to existing compounds. Furthermore, by introducing different substituents on the rigid skeleton, the delayed fluorescence lifetime and half-peak width can be further adjusted.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic electroluminescence, and in particular relates to an anthracene derivative containing multiple boron atoms, an organic electroluminescent material, a light-emitting device and a consumer product. Background Art

[0002] The materials used in organic electroluminescent devices are mostly pure organic compounds or organometallic complexes formed from organic compounds and metals. Depending on their application, they can be categorized as hole injectors, hole transporters, luminescent materials, electron transporters, and electron injectors. Hole injectors and hole transporters primarily use organic compounds with relatively low ionization energies, while electron injectors and electron transporters primarily use organic compounds with high electronegativity. Furthermore, the materials used in the luminescence-assisting layer preferably meet the following properties.

[0003] First, the substances used in organic electroluminescent elements need good thermal stability. The reason is that Joule heat is generated inside the organic electroluminescent element due to the migration of charges. At present, the glass transition temperature of the materials commonly used as hole transport layers is low. Therefore, when driven at low temperatures, the luminous efficiency decreases due to crystallization. Second, in order to reduce the driving voltage, the organic substances adjacent to the cathode and anode need to be designed to have a small charge injection barrier and a high charge mobility. Third, there are always energy barriers at the interface between the electrode and the organic layer, and at the interface between the organic layer and the organic layer, and some charges inevitably accumulate. Therefore, it is necessary to use substances with excellent electrochemical stability.

[0004] The luminescent layer consists of two substances: a primary emitter and a dopant. The dopant requires high quantum efficiency, and compared to the dopant, the primary emitter requires a larger band gap to facilitate energy transfer to the dopant. Displays used in televisions, mobile devices, and other applications achieve full color based on the three primary colors of red, green, and blue. The luminescent layers consist of a red primary emitter / dopant, a green primary emitter / dopant, and a blue primary emitter / dopant, respectively. Currently, blue-emitting materials still suffer from low quantum efficiency and poor color purity. This is primarily due to the fact that blue light originates from transitions between energy levels with wide band gaps, and wide-bandgap organic compounds present challenges in molecular design. Furthermore, the strong π-π bond interactions within the blue-emitting material system result in strong charge transfer properties, resulting in more nonradiative relaxation channels within the wide band gap. This exacerbates inter-molecular fluorescence quenching and reduces the quantum yield of the blue-emitting system.

[0005] In view of the above reasons, the present invention is proposed. Summary of the Invention

[0006] In order to solve the above problems existing in the prior art, the present invention provides an anthracene derivative containing multiple boron atoms, an organic electroluminescent material, a light-emitting device and a consumer product. The anthracene derivative of the present invention emits blue to deep blue light and has high luminous efficiency.

[0007] The first object of the present invention is to provide an anthracene derivative.

[0008] The second object of the present invention is to provide an organic electroluminescent material.

[0009] The third object of the present invention is to provide an organic electroluminescent device.

[0010] The fourth object of the present invention is to provide a consumer product.

[0011] In order to achieve the above object, the present invention adopts the following technical solutions:

[0012] An anthracene derivative, the general structural formula of the anthracene derivative is shown in formula (I):

[0013]

[0014] wherein Ring A is a five-membered heterocyclic ring, a six-membered carbocyclic ring, or a six-membered heterocyclic ring containing at least two carbon atoms;

[0015] R 1 、R 2 、R 3 、R 4 are independently selected from hydrogen, deuterium, halogen atoms, cyano groups, substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C1~C 30 Heteroalkyl, substituted or unsubstituted C3~C 30 Cycloalkyl, substituted or unsubstituted C6~C 60 Aryl, substituted or unsubstituted C2~C 60 Heteroaryl, substituted or unsubstituted C1~C 30 Alkoxy, substituted or unsubstituted C6~C 60 Aryloxy, substituted or unsubstituted C1~C 30 Alkylthio, substituted or unsubstituted C6~C 60 Arylthio, substituted or unsubstituted C1~C 30 Alkylamino, substituted or unsubstituted C6~C 60 Arylamine, substituted or unsubstituted C1~C 30 Alkylsilyl, substituted or unsubstituted C6~C 60 Arylsilyl, substituted or unsubstituted C2~C 30Alkenyl, or substituted or unsubstituted C2~C 30 A group consisting of alkynyl groups;

[0016] Ar 1 、Ar 2 are independently selected from hydrogen, deuterium, substituted or unsubstituted C6 to C 60 Aryl, substituted or unsubstituted C6~C 60 Arylamine, substituted or unsubstituted C2~C 60 The group consisting of heteroaryl;

[0017] R 1 、R 2 、R 3 、R 4 Each independently represents one or more substitutions to saturation.

[0018] An aryl group within the meaning of the present invention contains 6 to 60 carbon atoms, and a heteroaryl group within the meaning of the present invention contains 2 to 60 carbon atoms and at least one heteroatom, provided that the total number of carbon atoms and heteroatoms is at least 5; the heteroatoms are preferably selected from N, O or S. In this case, the two or more rings of the heteroaryl group may be attached to each other simply or in a condensed form, and further, may also include a condensed form with the aryl group. Non-limiting examples of aryl and heteroaryl groups include, in particular, the following groups: phenyl, naphthyl, anthracenyl, benzanthryl, phenanthrenyl, pyrenyl, phenyl, fluorenyl, peryl, fluoranthenyl, naphthacene, pentacene, benzopyrenyl, biphenyl, phenylene, terphenyl, triphenyl, quadriphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, triphenylene, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, cis- or trans-indenocarbazolyl, indolocarbazolyl, benzofuranocarbazolyl, benzothienocarbazolyl, benzocarbazolyl, dibenzocarbazolyl, azadibenzo[g,Id]naphtho[2,1,8-cde]indenyl, trimerized indenyl, isotrimerized indenyl, spirotrimerized indenyl, spiroistrimerized indenyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, pyridinyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo[5,6]quinolyl, benzo[6,7]quinolyl, benzo[7,8]quinolyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrazolyl, phenanthroxazolyl, isoxazolyl, 1,2- Thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazatriphenylenyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenoxazinyl, phenothiazinyl, fluorescein ring group, naphthyridinyl, azacarbazolyl, benzocarbolinyl, carbolinyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1 , 2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purinyl, pteridinyl, indolizinyl, quinazolinyl, benzothiadiazolyl or a group derived from a combination of these systems.

[0019] The alkyl group used in the present invention refers to a monovalent functional group obtained by removing one hydrogen atom from a straight-chain or branched saturated hydrocarbon having from 1 to 40 carbon atoms. Non-limiting examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl. Heteroalkyl refers to a hydrogen atom or -CH2- on an alkyl group substituted with at least one heteroatom selected from halogen, nitrile, N, O, S, or silicon. Non-limiting examples include monofluoromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl, pentafluoroethyl, nitrile, acetonitrile, methoxymethyl, methoxyethyl, trimethylsilyl, and triisopropylsilyl.

[0020] The alkenyl group used in the present invention refers to a monovalent functional group obtained by removing one hydrogen atom from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Non-limiting examples thereof include vinyl, allyl, isopropenyl, and 2-butenyl.

[0021] The alkynyl group used in the present invention refers to a monovalent functional group obtained by removing one hydrogen atom from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and one or more carbon-carbon triple bonds. Non-limiting examples thereof include ethynyl and 2-propynyl.

[0022] Generally speaking, cycloalkyl and cycloalkenyl groups according to the present invention refer to monovalent functional groups derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms by removing one hydrogen atom. Non-limiting examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, and cycloheptenyl, wherein one or more -CH2- groups may be replaced by the above groups; in addition, one or more hydrogen atoms may be replaced by a deuterium atom, a halogen atom, or a nitrile group.

[0023] The heterocycloalkyl group used in the present invention refers to a monovalent functional group obtained by removing one hydrogen atom from a non-aromatic hydrocarbon having 3 to 40 atomic nuclei. In this case, one or more carbon atoms, preferably 1 to 3 carbon atoms, in the ring are substituted with heteroatoms such as N, O, or S. Non-limiting examples include tetrahydrofuranyl, tetrahydrothienyl, morpholinyl, piperazinyl, pyranyl, and tetrahydropyranyl.

[0024] The alkoxy group used in the present invention refers to a monovalent functional group represented by RO-, where R is an alkyl group having 1 to 40 carbon atoms and may have a linear, branched, or cyclic structure. Non-limiting examples of such alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, n-butoxy, pentyloxy, cyclopentyloxy, and cyclohexyloxy.

[0025] The alkylthio group used in the present invention refers to R 0The monovalent functional group represented by s-, wherein R0 is an alkyl group having 1 to 40 carbon atoms, which may have a linear, branched, or cyclic structure. Non-limiting examples of such alkylthio groups include methylthio, ethylthio, n-propylthio, isopropylthio, tert-butylthio, and n-butylthio.

[0026] The aryloxy group used in the present invention refers to a monovalent functional group represented by R'O-, where R' is an aryl group having 6 to 60 carbon atoms. Non-limiting examples of such aryloxy groups include phenoxy, naphthyloxy, and biphenyloxy.

[0027] The arylthio group used in the present invention refers to a monovalent functional group represented by R"S-, where R" is an aryl group having 6 to 60 carbon atoms. Non-limiting examples of such arylthio groups include phenylthio, naphthylthio, and biphenylthio.

[0028] The "halogen" or "halogen atom" used in the present invention refers to a group selected from fluorine, chlorine, bromine or iodine.

[0029] The alkylsilyl group used in the present invention refers to a silyl group substituted by an alkyl group having 1 to 30 carbon atoms, wherein the number of carbon atoms constituting the alkylsilyl group is at least 3. Non-limiting examples of the alkylsilyl group include trimethylsilyl and triethylsilyl. The arylsilyl group refers to an alkylsilyl group substituted by at least one aryl group having 6 to 60 carbon atoms, and non-limiting examples include phenyldimethylsilyl, naphthyldimethylsilyl, phenyldiethylsilyl, diphenylmethylsilyl, diphenylethylsilyl, and triphenylsilyl.

[0030] The arylalkyl group of the present invention refers to an alkyl group in which at least one hydrogen atom of a linear or branched saturated hydrocarbon having 1 to 30 carbon atoms is substituted by an aryl group having 6 to 60 carbon atoms. Non-limiting examples thereof include phenylmethyl, diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl, and the like.

[0031] The alkylaryl group of the present invention refers to an aryl group having from 6 to 60 carbon atoms in which at least one hydrogen atom is substituted by a straight-chain or branched saturated hydrocarbon having from 1 to 30 carbon atoms. Non-limiting examples thereof include methylphenyl, dimethylphenyl, trimethylphenyl, tert-butylphenyl, isopropylphenyl, and the like.

[0032] The alkylamino group used in the present invention refers to an amino group substituted by an alkyl group having 1 to 40 carbon atoms, or a secondary amino group substituted by two alkyl groups having 1 to 40 carbon atoms. Non-limiting examples of the alkylamino group include methylamino, dimethylamino, ethylamino, diethylamino, and the like.

[0033] The arylamino group used in the present invention refers to an amino group substituted by an aryl group having 6 to 60 carbon atoms, or a secondary amino group substituted by two aryl groups having 6 to 60 carbon atoms, or a secondary amino group substituted by an alkyl group having 1 to 40 carbon atoms and an aryl group having 6 to 60 carbon atoms. Non-limiting examples of arylamino groups include aniline, diphenylamino, 1-naphthylamino, 2-naphthylamino, N-phenylnaphthalene-1-amino, carbazolyl, phenoxazinyl, and the like.

[0034] In the present invention, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, "ring" means a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle.

[0035] In the present invention, a five-membered heterocycle refers to a five-membered heteroaromatic ring containing at least two carbon atoms, and non-limiting examples include furan, thiophene, pyrrole, imidazole, benzofuran, benzothiophene, indole, etc. A six-membered carbocycle refers to a six-membered hydrocarbon ring or a six-membered aromatic ring containing at least two carbon atoms, and non-limiting examples include cyclohexane, cyclohexene, benzene, naphthalene, phenanthrene, etc. A six-membered heterocycle refers to a six-membered heterocyclic ring or a six-membered heteroaromatic ring containing at least two carbon atoms, and non-limiting examples include pyran, piperidine, pyridine, piperazine, pyrazine, etc.

[0036] Furthermore, the anthracene derivative is selected from the group consisting of the following structures:

[0037]

[0038] Wherein, G is selected from O, S, SO, SO2, NAr 3 ;

[0039] Ar 3 Selected from hydrogen, substituted or unsubstituted C6~C 60 Aryl, substituted or unsubstituted C6~C 60 Arylamine, substituted or unsubstituted C2~C 60 The group consisting of heteroaryl groups.

[0040] Furthermore, the R 1 、R 2 、R 3 、R 4 are independently selected from hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C3~C 30 Cycloalkyl, substituted or unsubstituted C6~C 60 Aryl, substituted or unsubstituted C2~C 60 Heteroaryl, substituted or unsubstituted C1~C 30 Alkoxy, substituted or unsubstituted C6~C 60A group consisting of arylamine groups.

[0041] Furthermore, the Ar 1 、Ar 2 、Ar 3 Each independently selected from hydrogen, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6~C 60 Arylamine, substituted or unsubstituted C2~C 60 The group consisting of heteroaryl groups.

[0042] Furthermore, the heteroaryl or heterocyclic aromatic group is a group consisting of the groups shown in II-1 to II-17, and the specific structures of II-1 to II-17 are as follows:

[0043]

[0044] wherein Z1 and Z2 are each independently selected from hydrogen, deuterium, halogen, hydroxyl, nitrile, nitro, amino, amidine, hydrazine, hydrazone, carboxyl or its carboxylate, sulfonic acid or its sulfonate, phosphate or its phosphate, C1-C 40 Alkyl, C2-C 40 Alkenyl, C2-C 40 Alkynyl, C1-C 40 Alkoxy, C3-C 40 Cycloalkane, C3-C 40 Cycloalkene, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Aryl sulfide group, or substituted or unsubstituted C2-C 60 The group consisting of heteroaryl;

[0045] x1 represents an integer from 1 to 4; x2 represents an integer from 1 to 3; x3 represents 1 or 2; x4 represents an integer from 1 to 6; x5 represents an integer from 1 to 5;

[0046] T1 represents an oxygen atom or a sulfur atom;

[0047] Represents the bond connecting the substituent to the main structure.

[0048] The substituted C6-C 60 Aryl, substituted C6-C 60 Aryloxy, substituted C6-C 60 Aryl sulfide, substituted C2-C 60wherein the substituent is selected from hydrogen, deuterium, halogen, hydroxyl, nitrile, nitro, amino, amidine, hydrazine, hydrazone, carboxyl or its carboxylate, sulfonic acid or its sulfonate, phosphate or its phosphate, C1-C 40 Alkyl, C2-C 40 Alkenyl, C2-C 40 Alkynyl, C1-C 40 Alkoxy, C3-C 40 Cycloalkane, C3-C 40 Cycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Aryl sulfide group, or C2-C 60 The group consisting of heterocyclic aromatic groups.

[0049] As used herein, "a combination thereof" or "a group thereof" means that one or more members of an applicable list are combined to form a known or chemically stable arrangement that one of ordinary skill in the art can conceive from the applicable list. For example, an alkyl group and a deuterium group can be combined to form a partially or fully deuterated alkyl group; a halogen and an alkyl group can be combined to form a haloalkyl substituent, such as a trifluoromethyl group; and a halogen, an alkyl group, and an aryl group can be combined to form a haloaralkyl group.

[0050] Furthermore, the anthracene derivative is one of the following structures B751 to B879:

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060] Here, the hydrogen atoms in the structure may be partially or completely replaced by deuterium atoms.

[0061] An organic electroluminescent material comprises the anthracene derivative containing multiple boron atoms.

[0062] The organic electroluminescent material may be composed of the compound of the present invention alone, or may contain other compounds simultaneously.

[0063] The compound of the present invention contained in the organic electroluminescent material of the present invention can be used as, but not limited to, a light-emitting layer material.

[0064] An organic electroluminescent device comprises a first electrode, a second electrode and at least one organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises an anthracene derivative provided by the present invention.

[0065] The organic electroluminescent device comprises a cathode, an anode and at least one light-emitting layer. In addition to these layers, it may also comprise other layers, for example, in each case, one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers and / or charge generation layers. An intermediate layer having, for example, an exciton blocking function may also be introduced between two light-emitting layers. However, it should be noted that each of these layers does not necessarily have to be present. The organic electroluminescent device described herein may comprise one light-emitting layer, or it may comprise multiple light-emitting layers. That is, a variety of light-emitting compounds that are capable of emitting light are used in the light-emitting layer. Preferably, a system with three light-emitting layers is provided, wherein the three layers can exhibit blue, green and red light emission. If there is more than one light-emitting layer, according to the present invention, at least one of these layers comprises a compound of the present invention.

[0066] Furthermore, the organic electroluminescent device according to the present invention does not include a separate hole injection layer and / or hole transport layer and / or hole blocking layer and / or electron transport layer, that is, the light-emitting layer is directly adjacent to the hole injection layer or the anode, and / or the light-emitting layer is directly adjacent to the electron transport layer or the electron injection layer or the cathode.

[0067] In the other layers of the organic electroluminescent device according to the invention, in particular in the hole injection and hole transport layers as well as in the electron injection and electron transport layers, all materials can be used in the manner commonly used according to the prior art. A person skilled in the art will therefore be able to use all materials known for organic electroluminescent elements in combination with the emitting layer according to the invention without inventive step.

[0068] Furthermore, preference is given to organic electroluminescent devices in which one or more layers are applied by means of a sublimation method, wherein the organic electroluminescent device is deposited in a vacuum sublimation device at temperatures below 10 -5 Pa, preferably less than 10 -6 The material is applied by vapor deposition at an initial pressure of 10 Pa. However, the initial pressure may also be even lower, for example below 10 -7 Pa.

[0069] Likewise preferred are organic electroluminescent devices in which one or more layers are applied by means of an organic vapor phase deposition method or by means of carrier gas sublimation, wherein at 10 -5 The material is applied at a pressure between 100 Pa and 1 Pa. A particular example of this method is the organic vapor jet printing method, in which the material is applied directly through a nozzle and is thus structured.

[0070] Furthermore, organic electroluminescent devices are preferred in which one or more layers are produced from solution, for example by spin coating, or by any desired printing method, such as screen printing, flexographic printing, lithographic printing, photoinduced thermography, thermal transfer printing, inkjet printing, or nozzle printing. Soluble compounds are obtained, for example, by appropriate substitution of compounds of formula (I). These methods are also particularly suitable for oligomers, dendrimers, and polymers. Hybrid methods are also possible, in which, for example, one or more layers are applied from solution and one or more additional layers are applied by vapor deposition.

[0071] These methods are generally known to those skilled in the art, and they can apply them to organic electroluminescent elements comprising the compounds according to the invention without inventive step.

[0072] The present invention therefore also relates to a method for producing an organic electroluminescent device according to the invention, which applies at least one layer by means of a sublimation method and / or applies at least one layer by means of an organic vapor phase deposition method or by means of carrier gas sublimation and / or applies at least one layer from solution by spin coating or by means of a printing method.

[0073] In addition, the present invention relates to a compound of the present invention comprising at least one of the compounds of the present invention indicated above. The same preferences as indicated above for organic electroluminescent devices apply to the compounds of the present invention. In particular, the compounds may also preferably comprise other compounds. Processing the compounds of the present invention from the liquid phase, for example by spin coating or by a printing method, requires a formulation for processing the compounds of the present invention. These formulations may, for example, be solutions, dispersions or emulsions. For this purpose, a mixture of two or more solvents may preferably be used. Suitable and preferred solvents are, for example, toluene, anisole, o-xylene, m-xylene or p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, tetrahydrofuran, methyltetrahydrofuran, tetrahydropyran, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, α-terpenes benzothiazole, butyl benzoate, isopropylbenzene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, 1-methylpyrrolidone, p-cymene, phenethyl ether, 1,4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, or a mixture of these solvents.

[0074] Furthermore, the organic layer is selected from one or more of an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer, a hole injection layer and a light-emitting layer.

[0075] Furthermore, the light-emitting layer comprises the anthracene derivative of the present invention.

[0076] Furthermore, the light-emitting layer includes a dopant and a light-emitting host, and the host includes anthracene, naphthalene, anthracene, pyrene, perylene, phenanthrene, fluoranthene, The group consisting of benzanthracene, fluorene, spirofluorene and pentacene and their derivatives; the dopant comprises the anthracene derivative of the present invention.

[0077] Furthermore, the mass ratio of the dopant to the light-emitting host is 1:99 to 50:50.

[0078] A consumer product made from the organic electroluminescent device, wherein the consumer product includes the organic electroluminescent device provided by the present invention.

[0079] The consumer product described in the present invention can be one of the following products: flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior lighting and / or signaling, heads-up displays, fully or partially transparent displays, flexible displays, laser printers, telephones, cellular phones, tablet computers, phablets, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, video cameras, viewfinders, microdisplays with a diagonal of less than 2 inches, 3-D displays, virtual reality or augmented reality displays, vehicles, video walls comprising multiple displays tiled together, theater or stadium screens, light therapy devices, and signage.

[0080] Unless otherwise specified, the raw materials used in the present invention can be obtained commercially. Any range described in the present invention includes the end value and any numerical value between the end values ​​and any sub-range formed by the end value or any numerical value between the end values.

[0081] Compared with the prior art, the present invention has the following beneficial effects:

[0082] The anthracene derivatives described in the present invention are novel organic electroluminescent compounds having a large planar conjugated structure formed by anthracene and a seven-membered ring. The seven-membered ring anthracene derivatives achieve HOMO and LUMO separation through the boron-nitrogen resonance effect, thereby realizing the thermally activated delayed fluorescence (TADF) effect and achieving a shorter emission wavelength compared to existing compounds; thereby improving the efficiency and lifespan of organic electroluminescent devices containing the compounds; in addition, the compounds improve their solubility in solution, thereby solving the productivity and cost problems of the process previously encountered with blue light materials, and can also be used to prepare a light-emitting layer in the original process rather than the vapor deposition process. BRIEF DESCRIPTION OF THE DRAWINGS

[0083] In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the following briefly introduces the drawings required for use in the embodiments or the description of the prior art. Obviously, the drawings described below are only some embodiments of the present invention. For ordinary technicians in this field, other drawings can be obtained based on these drawings without paying any creative work.

[0084] Figure 1 A schematic diagram of an organic light-emitting device 100 is shown. The illustration is not necessarily drawn to scale. Device 100 may include a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light-emitting layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer (CPL) 111. Device 100 can be fabricated by depositing the described layers in order.

[0085] Figure 2 A schematic diagram of an organic light-emitting device 200 showing two light-emitting layers. The device includes a substrate 201, an anode 202, a hole injection layer 203, a hole transport layer 204, a first light-emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second light-emitting layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. Device 200 can be fabricated by sequentially depositing the described layers. While most common OLED devices have a single light-emitting layer, device 200 has a first light-emitting layer and a second light-emitting layer. The emission peaks of the first and second light-emitting layers can overlap, overlap, or not overlap. Materials similar to those described for device 100 can be used in the corresponding layers of device 200. Figure 2 An example of how to add some layers from the structure of the device 100 is provided. DETAILED DESCRIPTION

[0086] To make the objectives, technical solutions, and advantages of the present invention more apparent, the technical solutions of the present invention will be described in detail below. Obviously, the embodiments described are only some of the embodiments of the present invention, not all of them. Based on the embodiments of the present invention, all other implementations obtained by those of ordinary skill in the art without inventive effort are within the scope of protection of the present invention.

[0087] In the present invention, preparation methods are conventional methods unless otherwise specified. Raw materials used are commercially available unless otherwise specified, and percentages are by mass unless otherwise specified. All reactions in the series of novel organic compounds provided by the present invention are carried out under well-known suitable conditions. Some reactions involve simple organic preparations, such as the preparation of N,N-diphenylamine derivatives, which can be synthesized by skilled operators and are not described in detail herein.

[0088] The following examples use the following testing instruments and methods to test the performance of OLED materials and components:

[0089] OLED component performance test conditions:

[0090] Brightness and chromaticity coordinates: tested using a spectrum scanner PhotoResearch PR-715;

[0091] Current density and turn-on voltage: tested using a Keithley 2420 digital source meter;

[0092] Power efficiency: tested using NEWPORT 1931-C;

[0093] Life test: Use LTS-1004AC life test device.

[0094] Example 1

[0095] The preparation method of compound B751 comprises the following steps:

[0096] Step 1: Preparation of compound Int.-1

[0097]

[0098] Under nitrogen protection, 50.0 mmol of o-iodobromobenzene was dissolved in 100 mL of dry tetrahydrofuran, cooled to 0°C, and 52.0 mL of 1 M isopropylmagnesium bromide THF solution was added dropwise. The mixture was stirred and reacted for 1 hour. A solution of 48.0 mmol of 9H-tribenzo[a,c,e][7]cycloannulene-9-one (CAS: 68089-73-6) dissolved in THF was added dropwise. The mixture was heated to room temperature and stirred and reacted for 2 hours. 50 mL of 2 M dilute hydrochloric acid aqueous solution was added, and the mixture was extracted with ethyl acetate. The organic phase was collected, dried, filtered, and the filtrate was concentrated and dried under reduced pressure. The intermediate Int.-1 was obtained by separation and purification using a silica gel column. The yield was 94%.

[0099] Step 2: Preparation of compound Int.-2

[0100]

[0101] Under nitrogen protection, 40.0 mmol of Int.-1 prepared in the first step was dissolved in 100 mL of dichloromethane, 80.0 mmol of triethylsilane was added, the temperature was lowered to 0°C, 30 mL of trifluoroacetic acid was slowly added dropwise, the temperature was raised to room temperature and stirred for 12 hours, 50 mL of water was added, and the mixture was extracted with dichloromethane. The organic phase was collected, dried, and filtered. The filtrate was concentrated under reduced pressure and dried, and then separated and purified using a silica gel column to obtain Int.-2 with a yield of 82%.

[0102] Step 3: Preparation of Compound Int.-3

[0103]

[0104] 50.0 mmol of the intermediate Int.-2 prepared in the second step was dissolved in 120 mL of dry THF. Under nitrogen protection, the temperature was lowered to -78°C, and 22.0 mL of 2.5 M n-butyllithium n-hexane solution was added dropwise. The mixture was stirred and reacted for 1 hour. 75.0 mmol of DMF was added dropwise, and the mixture was warmed to room temperature and stirred and reacted for 1 hour. 50 mL of 2 M dilute hydrochloric acid aqueous solution was added, the organic phase was separated, and the aqueous phase was extracted with dichloromethane. The organic phase was collected, dried and filtered, and the filtrate was concentrated and dried under reduced pressure. It was separated and purified using a silica gel column to obtain Int.-3 with a yield of 87%.

[0105] Step 4: Preparation of Compound Int.-4

[0106]

[0107] Under nitrogen protection, 40.0 mmol of intermediate Int.-3 was dissolved in 80 mL of dichloromethane, and 8.0 mmol of boron trifluoride ether solution was added. The mixture was stirred at room temperature for 1 hour, concentrated and dried under reduced pressure, and separated and purified by silica gel column to obtain intermediate Int.-4 with a yield of 92%.

[0108] Step 5: Preparation of Compound Int.-5

[0109]

[0110] 41.2 mmol of intermediate Int.-4 was dissolved in 120 mL of dichloromethane, cooled to 0°C in an ice-water bath, 4.1 mmol of p-toluenesulfonic acid was added, and 42.0 mmol of NBS was added in batches. The reaction was stirred for 2 hours, and 100 mL of 10% sodium bicarbonate aqueous solution was added. The organic phase was separated and washed with water. The organic phase was collected, dried, filtered, and the filtrate was concentrated and dried under reduced pressure. It was separated and purified using a silica gel column to obtain compound Int.-5 with a yield of 96%.

[0111] Step 6: Preparation of Compound Int.-6

[0112]

[0113] Under nitrogen protection, 20.0 mmol of intermediate Int.-5 was dissolved in 60 mL of dry THF, 24.0 mmol of triisopropyl borate was added, the temperature was lowered to -100°C, 24.0 mmol of 2.5 M n-butyl lithium n-hexane solution was added dropwise, the reaction was stirred for 1 hour, the temperature was raised to room temperature, 50 mL of 2 M dilute hydrochloric acid aqueous solution was added dropwise, the organic phase was separated, the aqueous phase was extracted with ethyl acetate, the organic phase was collected, dried, filtered, the filtrate was concentrated under reduced pressure, petroleum ether was added for dispersion, filtered, and the filter cake was washed with petroleum ether to obtain compound Int.-6 as a yellow solid with a yield of 78%.

[0114] Step 7: Preparation of Compound Int.-7

[0115]

[0116] 20.0 mmol of the intermediate Int.-6 was dispersed in 100 mL of dry toluene, and 40.0 mmol of o-phenylenediamine, 22.0 mmol of p-toluenesulfonic acid, and 2.0 mmol of anhydrous magnesium sulfate were added. The temperature was raised to reflux and stirred for 24 hours. The mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and purified using a silica gel column to obtain compound Int.-7 as a yellow solid in a yield of 67%.

[0117] Step 8: Preparation of compound B751

[0118]

[0119] Under nitrogen protection, 10.0 mmol of intermediate Int.-7 was dispersed in 50 mL of dry o-dichlorobenzene, 25.0 mmol of boron tribromide was added, the temperature was raised to reflux with stirring, and the reaction was carried out for 24 hours. The temperature was then cooled to room temperature, and 75.0 mmol of a 1 M 2,4,6-trimethylphenylmagnesium bromide toluene / THF solution was added. The reaction was stirred at room temperature for 6 hours, and 50 mL of water was added. The organic phase was separated, and the aqueous phase was extracted with dichloromethane. The organic phase was collected, dried, filtered, and the filtrate was concentrated to dryness under reduced pressure. The compound was separated and purified by silica gel column chromatography to obtain compound B751 as a yellow solid in a 30% yield. HRMS (ESI) m / z 701.3404 [M+H] + ; 1 HNMR (δ, CDCl3): 8.43~8.38 (4H, m); 8.18~8.15 (1H, m); 8.09~8.03 (4H, m); 7.64~7.62 (1H, d); 7.48 ~7.42 (3H, m); 7.07 ~ 7.04 (4H, m); 6.97 ~ 6.91 (2H, m); 6.87 ~ 6.80 (2H, m); 2.48 (6H, s); 2.26 (12H, s).

[0120] Example 2

[0121] The preparation method of compound B757 and compound B759 comprises the following steps:

[0122] Step 1: Preparation of Compound Int.-8

[0123]

[0124] Referring to the synthesis method of the seventh step of Example 1, only the o-phenylenediamine in the seventh step of Example 1 was replaced by sub-1 (prepared according to the synthesis method disclosed in patent CN114560872A) to prepare compound Int.-8 with a yield of 64%.

[0125] Step 2: Preparation of Compound B757 and Compound B759

[0126]

[0127] Under nitrogen protection, 10.0 mmol of intermediate Int.-8 was dispersed in 50 mL of dry o-dichlorobenzene, 25.0 mmol of boron tribromide was added, the temperature was raised to reflux with stirring, and the reaction was carried out for 24 hours. The temperature was then cooled to room temperature, and 75.0 mmol of a 1 M 2,4,6-trimethylphenylmagnesium bromide toluene / THF solution was added. The reaction was stirred at room temperature for 15 hours, and 50 mL of water was added. The organic phase was separated, and the aqueous phase was extracted with dichloromethane. The organic phase was collected, dried, filtered, and the filtrate was concentrated to dryness under reduced pressure. The compound was separated and purified by silica gel column chromatography to obtain compound B757 as a yellow solid in a yield of 24%. HRMS (ESI) m / z 979.5079 [M+H] + , 1 HNMR (δ, CDCl3): 8.43-8.38 (4H, m); 8.18-8.15 (1H, m); 8.09-8.03 (4H, m); 7.63-7.61 (1H, d); 7.54-7.46 (5H, m); 7.37-7.32 (2H, m); 7.28-7.23 (2H, m); 7.20-7.19 (1H, d); 7.12 (1H, s); 7.04-7.02 (4H, m); 2.37 (12H, s); 2.18 (6H, s); 1.42 (9H, s); 1.29 (9H, s); compound B759 was obtained as a yellow solid in a yield of 9%. HRMS (ESI) m / z 979.5075[M+H] + , 1 HNMR (δ, CDCl3): 8.43~8.38(4H, m); 8.18~8.15(1H, m); 8.09~8.03(4H, m); 7.64~7.62(1H, d); 7.52~7.45(5H, m); 7.37~7.32(2H, m); 7.30~7.25 (2H, m); 7.21~7.19 (1H, d); 7.12 (1H, s); 7.04~7.02 (4H, m); 2.48 (12H, s); 2.18 (6H, s); 1.43 (9H, s); 1.32 (9H, s).

[0128] Example 3 to Example 128

[0129] The following compounds were prepared by using similar synthetic methods as described in Examples 1 and 2:

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141] Application Examples 1 to 129

[0142] An OLED element 100, such as Figure 1 As shown, the OLED element of this embodiment is a top-emitting light element, including a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light-emitting layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer (CPL) 111. The OLED element omits the hole blocking layer 107, and the preparation method includes the following steps:

[0143] 1) A glass substrate coated with an ITO conductive layer was ultrasonically treated in a cleaning agent for 30 minutes, rinsed in deionized water, ultrasonically treated in an acetone / ethanol mixed solvent for 30 minutes, baked in a clean environment until completely dry, irradiated with an ultraviolet light cleaner for 10 minutes, and bombarded with a low-energy cation beam.

[0144] 2) Place the treated ITO glass substrate in a vacuum chamber and evacuate the chamber to a vacuum of less than 1×10- 5 Pa, silver is evaporated on the above ITO film as the anode 102, and the evaporated film thickness is Continue to evaporate the compound DNTPD and F4TCNQ as the hole injection layer 103, wherein F4TCNQ is 3% of the mass of DNTPD, and the evaporated film thickness is NPD is continuously evaporated on the hole injection layer to form the hole transport layer 104, with a thickness of

[0145] 3) Continue to evaporate a layer of compound HT202 on the hole transport layer as the electron blocking layer 105, the evaporated film thickness is

[0146] 4) A layer of anthracene derivative represented by formula (I) of the present invention and BH017 is continuously evaporated on the electron blocking layer as an organic light-emitting layer 106, wherein BH017 is a main material and the anthracene derivative represented by formula (I) of the present invention is a doping material, the doping concentration of the anthracene derivative represented by formula (I) in BH017 is 5%, and the evaporated film thickness is

[0147] 5) A layer of compound LiQ and ET205 is further evaporated on the above-mentioned light-emitting layer as the electron transport layer 108 of the device, wherein the mass ratio of LiQ and ET205 is 1:1, and the evaporated film thickness is

[0148] 6) A layer of LiF compound is further evaporated on the electron transport layer as the electron injection layer 109 of the device. The thickness of the evaporated film is

[0149] 7) On the electron injection layer, magnesium and silver are evaporated as the transparent cathode 110 of the element, wherein the mass ratio of magnesium to silver is 2:1 and the thickness of the evaporated film is

[0150] Finally, a layer of compound NPD is evaporated on the transparent cathode as a capping layer 111, with a thickness of 500 Å.

[0151] The structures of the compounds used in the above examples are as follows:

[0152]

[0153] Application Example 130

[0154] An organic electroluminescent element 200 is a top-emitting multi-light-emitting element, and its structure is as follows: Figure 2 As shown, the device includes a substrate 201, an anode 202, a hole injection layer 203, a hole transport layer 204, a first light-emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second light-emitting layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. The element can be prepared by depositing the described layers in order.

[0155] Because the most common organic electroluminescent device has a single-color light-emitting layer or three light-emitting layers of three primary colors, Figure 2 The element shown has two light-emitting layers of the same color, and the emission peaks of the first light-emitting layer and the second light-emitting layer of the element may be overlapping, cross-overlapping, or non-overlapping. Figure 2 The corresponding layers of the elements shown can be used in conjunction with Figure 1The elements shown are made of similar materials to those described. Figure 2 Provides information on how to Figure 1 The structure of the element shown is an example of adding some layers. The specific preparation method is the same as Figure 1 The OLED element shown. Figure 1 and Figure 2 The simple layered structures illustrated in are provided as non-limiting examples, and it will be understood that embodiments of the invention may be used in conjunction with a wide variety of other structures. The specific materials and structures described are exemplary in nature, and other materials and structures may be used. Functional OLEDs may be achieved by combining the various layers described in different ways, or several layers may be omitted entirely, based on design, performance, and cost factors. Other layers not specifically described may also be included. Materials other than those specifically described may be used. Although many of the examples provided herein describe the various layers as comprising a single material, it will be understood that combinations of materials may be used, such as a mixture of a host and a dopant, or more generally, a mixture. Furthermore, the layers may have various sub-layers. The names given to the various layers herein are not intended to be strictly limiting. For example, in Figure 2 In the element shown, the hole transport layer 204 transports holes and injects holes into the first light emitting layer 205 and can be described as a hole transport layer or an electron blocking layer. In one embodiment, the OLED can be described as having an organic layer disposed between a cathode and an anode. This organic layer can include a single layer or can further include, for example, Figure 1 and Figure 2 Multiple layers of different organic materials are described.

[0156] The specific preparation method is the same as that of the OLED element described in Application Example 1 above.

[0157] Comparative Example 1

[0158] The same steps as in Application Example 1 are followed, except that compound B3N is used instead of the anthracene derivative represented by formula (I). The structure of compound B3N is:

[0159]

[0160] The organic electroluminescent element prepared by the above process was subjected to the following performance tests:

[0161] The driving voltage, current efficiency, and life of the organic electroluminescent elements prepared in Application Examples 1 to 130 and Comparative Example 1 were measured using a digital source meter and a luminance meter. Specifically, the voltage was increased at a rate of 0.1 V per second, and the current density of the organic electroluminescent element was measured when it reached 10 mA / cm 2The voltage at this time is the driving voltage, and the brightness at this time is measured at the same time; the ratio of brightness to current density is the current efficiency; the LT95% life test is as follows: use a luminance meter at 1000cd / m 2 Under the same brightness, the current is kept constant and the brightness decay of the organic electroluminescent element is measured to be 950cd / m 2 The data listed in Table 2 are relative data compared with the comparative example element 1.

[0162] Table 2

[0163]

[0164]

[0165]

[0166] As can be seen from Table 2, the anthracene derivatives of the present invention are used as blue light doping materials to obtain a deep blue light organic electroluminescent element. Compared with the organic electroluminescent element using B3N as a blue light doping material, the current efficiency is higher, the driving voltage is lower, the full-height half-maximum width of the luminescence peak is narrowed, and the initial brightness of the device is 1000 cd / m 2 Under the starting conditions, the LT90% life of the device is also greatly improved.

[0167] The main difference between the anthracene derivatives of the present invention and the compound B3N of comparative example 1 is that the 9-phenylanthracene of B3N as the donor part has a small conjugated area, while the donor part of the anthracene derivatives of the present invention is a large planar conjugation of seven-membered ring anthracene, the conjugated area is increased, and the exciton transmission ability is enhanced. Therefore, under the action of boron-nitrogen atom resonance, the TADF effect is realized, the luminescence efficiency is improved, and excellent luminescence performance is exhibited.

[0168] The organic electroluminescent device of the present invention can be used in flat-panel luminous bodies such as wall-mounted televisions, flat-panel displays, lighting, backlight sources of copiers, printers, liquid crystal displays, light sources of measuring instruments, display panels, signage, etc.

[0169] The above description is merely a specific embodiment of the present invention, but the scope of protection of the present invention is not limited thereto. Any modifications or substitutions that can be easily conceived by a person skilled in the art within the technical scope disclosed in the present invention should be included in the scope of protection of the present invention. Therefore, the scope of protection of the present invention should be based on the scope of protection of the claims.

Claims

1. An anthracene derivative, characterized in that The anthracene derivative is selected from the group consisting of the following structures: 、 、 ； Wherein, G is selected from O, S, NAr 3 ; R 1 、R 2 、R 3 、R 4 are each independently selected from the group consisting of hydrogen, deuterium, cyano, methyl, ethyl, isopropyl, isobutyl, tert-butyl, phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthrenyl, triphenylene, anthracenyl, benzanthryl, pyrenyl, chrysyl, peryl, fluoranthenyl, carbazolyl, fluorenyl, indolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, or triazinyl; Ar 1 、Ar 2 、Ar 3 are each independently selected from the group consisting of phenyl, naphthyl, anthracenyl, benzanthryl, phenanthrenyl, pyrenyl, chrysyl, peryl, fluoranthenyl, pentacene, benzopyrenyl, biphenyl, phenylene, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, triphenylene, dihydropyrenyl, tetrahydropyrenyl, indolocarbazolyl, benzofurocarbazolyl, benzothienocarbazolyl, benzocarbazolyl, dibenzocarbazolyl, trimerized indenyl, isotrimerized indenyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothiophene phenyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, pyridinyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo[5,6]quinolyl, benzo[6,7]quinolyl, benzo[7,8]quinolyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrazolyl, phenanthroxazolyl, isoxazolyl, 1, 2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazatriphenylenyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, carbolinyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazole oxazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purinyl, pteridinyl, indolizinyl, quinazolinyl, or benzothiadiazolyl.

2. An anthracene derivative, characterized in that The anthracene derivative is one of the following structures:

3. An organic electroluminescent material, characterized in that: The organic electroluminescent material comprises the anthracene derivative according to any one of claims 1-2.

4. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises a first electrode, a second electrode and at least one organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises the anthracene derivative according to any one of claims 1 to 2.

5. The organic electroluminescent device according to claim 4, wherein: The organic layer is selected from one or more of an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer, a hole injection layer and a light-emitting layer; The light-emitting layer comprises the anthracene derivative according to any one of claims 1 to 2.

6. The organic electroluminescent device according to claim 5, wherein: The light-emitting layer includes a dopant and a light-emitting host, wherein the light-emitting host is selected from the group consisting of anthracene, naphthalene, pyrene, perylene, phenanthrene, fluoranthene, chrysene, benzanthracene, fluorene and pentacene; and the dopant includes the anthracene derivative according to any one of claims 1 to 2.

7. The organic electroluminescent device according to claim 6, wherein: The mass ratio of the dopant to the luminescent host is 1:99 to 50:

50.

8. A consumer product, characterized in that: The organic electroluminescent device according to claim 4 is included.

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