CN116715686A - Anthracene derivative containing multiple boron atoms and application thereof - Google Patents

Anthracene derivative containing multiple boron atoms and application thereof Download PDF

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CN116715686A
CN116715686A CN202310404690.6A CN202310404690A CN116715686A CN 116715686 A CN116715686 A CN 116715686A CN 202310404690 A CN202310404690 A CN 202310404690A CN 116715686 A CN116715686 A CN 116715686A
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anthracene derivative
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曹建华
郭晓慧
董梁
申旭
梁红红
秦子杰
张宇炜
宗冠华
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Beijing Bayi Space LCD Technology Co Ltd
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Beijing Bayi Space LCD Technology Co Ltd
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Abstract

The invention relates to an anthracene derivative containing a plurality of boron atoms, an organic electroluminescent material, a light-emitting device and a consumer product, wherein the anthracene derivative is provided with a novel organic electroluminescent compound with a large-ring planar structure of anthracene and seven-membered ring, and the seven-membered ring anthracene derivative realizes HOMO and LUMO separation through the resonance effect between boron and nitrogen, thereby realizing the TADF effect and realizing shorter light-emitting wavelength compared with the existing compound; on the other hand, by introducing different substituents on the rigid skeleton, further adjustment of the delayed fluorescence lifetime and half-width can be achieved.

Description

Anthracene derivative containing multiple boron atoms and application thereof
Technical Field
The invention belongs to the technical field of organic electroluminescence, and particularly relates to an anthracene derivative containing a plurality of boron atoms, an organic electroluminescent material, a light-emitting device and a consumer product.
Background
Most of the materials used in the organic electroluminescent element are pure organic materials or organometallic complexes of organic materials and metals, and they are classified into hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials, and the like, depending on the application. Here, an organic substance having a relatively small ionization energy is mainly used as the hole injection substance or the hole transport substance, and an organic substance having a relatively large electronegativity is mainly used as the electron injection substance or the electron transport substance. Further, the substance used as the light-emitting auxiliary layer preferably satisfies the following characteristics.
First, the materials used in the organic electroluminescent element are required to have good thermal stability because joule heat is generated by charge transfer in the organic electroluminescent element, and at present, the glass transition temperature of the materials generally used as the hole transport layer is low, so that the phenomenon of lowering of light emission efficiency due to crystallization occurs at the time of driving at low temperature occurs. Second, in order to reduce the driving voltage, it is necessary to design the organic material adjacent to the cathode and anode so that the charge injection barrier is small and the charge mobility is high. Third, there is always an energy barrier at the interface of the electrode and the organic layer, and at the interface of the organic layer and the organic layer, and some charges are inevitably accumulated, so that it is necessary to use a substance excellent in electrochemical stability.
The light-emitting layer is composed of two substances, i.e., a host light-emitting body and a dopant, and the dopant needs to have high quantum efficiency, and the host light-emitting body needs to have a larger energy gap than the dopant, so that energy transfer to the dopant is likely to occur. Displays for televisions, mobile devices, etc. realize full colors according to three primary colors of red, green, blue, and the light emitting layer is composed of a red main light emitter/dopant, a green main light emitter/dopant, and a blue main light emitter/dopant, respectively. At present, the blue light material still has the problems of low luminous quantum efficiency and poor color purity. The main reason for this situation is that blue light comes from the transition between energy levels with wider energy gaps, while organic compounds with wide forbidden bands have certain difficulties in molecular design, and secondly, the blue light material system has stronger pi-pi bond interaction and has strong charge transfer characteristics, so that more non-radiative relaxation channels exist in the wide energy gaps, fluorescence quenching among molecules is aggravated, and quantum yield of the blue light system is reduced.
The present invention has been made in view of the above-mentioned circumstances.
Disclosure of Invention
In order to solve the problems in the prior art, the invention provides an anthracene derivative containing a plurality of boron atoms, an organic electroluminescent material, a light-emitting device and a consumer product, wherein the anthracene derivative emits light from blue to deep blue and has high light-emitting efficiency.
The first object of the present invention is to provide an anthracene derivative.
The second object of the present invention is to provide an organic electroluminescent material.
A third object of the present invention is to provide an organic electroluminescent device.
A fourth object of the present invention is to provide a consumer product.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
an anthracene derivative, wherein the structural general formula of the anthracene derivative is shown as a formula (I):
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;
R 1 、R 2 、R 3 、R 4 each independently selected from the group consisting of hydrogen, deuterium, halogen atoms, cyano groups, substituted or unsubstituted C 1 ～C 30 Alkyl, substituted or unsubstituted C 1 ～C 30 Heteroalkyl, substituted or notSubstituted C 3 ～C 30 Cycloalkyl, substituted or unsubstituted C 6 ～C 60 Aryl, substituted or unsubstituted C 2 ～C 60 Heteroaryl, substituted or unsubstituted C 1 ～C 30 Alkoxy, substituted or unsubstituted C 6 ～C 60 Aryloxy, substituted or unsubstituted C 1 ～C 30 Alkylthio, substituted or unsubstituted C 6 ～C 60 Arylthio, substituted or unsubstituted C 1 ～C 30 Alkylamino, substituted or unsubstituted C 6 ～C 60 Arylamine group, substituted or unsubstituted C 1 ～C 30 Alkylsilyl, substituted or unsubstituted C 6 ～C 60 Arylsilyl, substituted or unsubstituted C 2 ～C 30 Alkenyl, or substituted or unsubstituted C 2 ～C 30 Alkynyl groups;
Ar 1 、Ar 2 each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C 6 ～C 60 Aryl, substituted or unsubstituted C 6 ～C 60 Arylamine group, substituted or unsubstituted C 2 ～C 60 Heteroaryl groups;
R 1 、R 2 、R 3 、R 4 each independently represents one or more to saturated substitutions.
Aryl groups in the sense of the present invention contain 6 to 60 carbon atoms, heteroaryl groups in the sense of the present invention contain 2 to 60 carbon atoms and at least one heteroatom, provided that the sum of carbon atoms and heteroatoms is at least 5; the heteroatom is preferably selected from N, O or S. In this case, two or more rings of the heteroaryl group may be attached to each other simply or in a condensed form, or may further include a condensed form with the aryl group. As non-limiting examples of aryl and heteroaryl groups, in particular groups selected from the following: phenyl, naphthyl, anthryl, benzanthraceyl, phenanthryl, pyrenyl, A group, perylene group, fluoranthenyl group, naphthacene group, pentacene group, benzopyrene group, biphenyl group, terphenyl group, tripolyphenyl group, tetrabiphenyl group, fluorenyl group, spirobifluorenyl group, dihydrophenanthrene group, triphenylene group, dihydropyrenyl group, tetrahydropyrenyl group, cis-or trans-indenofluorenyl group, cis-or trans-indenocarbazolyl group, indolocarbazolyl group, benzofuranocarbazolyl group, benzothiophenocarbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, azadibenzo [ g, id]Naphtho [2,1,8-cde]Diatom, trimeric indenyl, heterotrimeric indenyl, spirotrimeric indenyl, spiroheterotrimeric indenyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo [5,6 ]]Quinolinyl, benzo [6,7]Quinolinyl, benzo [7,8]Quinolinyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthaminyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthazolyl, anthracnose oxazolyl, phenanthrooxazolyl, isoxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazabenzophenanthryl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl, 2, 7-diazapyrenyl, 2, 3-diazapyrenyl, 1, 6-diazapyrenyl, 1, 8-diazapyrenyl, 4,5,9, 10-tetraazaperylene, pyrazinyl, phenazinyl, phenoxazinyl, phenothiazinyl, fluorozinyl, naphthyridinyl, azacarbazolyl, benzocarboline yl, carboline yl, phenanthroline yl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazole, 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.
The alkyl group used in the present invention means a monovalent functional group obtained by removing one hydrogen atom from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. As non-limiting examples thereof, there are methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl and the like. Heteroalkyl means a hydrogen atom or-CH on the alkyl radical 2 Substituted with at least one heteroatom selected from halogen, nitrile, N, O, S or silicon, as non-limiting examples, monofluoromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl, pentafluoroethyl, nitrile, acetonitrile, methoxymethyl, methoxyethyl, trimethylsilyl, triisopropylsilyl and the like.
The alkenyl group used in the present invention means 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. As non-limiting examples thereof, there are vinyl, allyl, isopropenyl, 2-butenyl, and the like.
Alkynyl as used in the present invention means 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 triple bonds. As non-limiting examples thereof, there are ethynyl, 2-propynyl and the like.
In general, cycloalkyl, cycloalkenyl according to the present invention refers to monovalent functional groups derived from the removal of one hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. As non-limiting examples thereof, there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, wherein one or more-CH 2 The groups may be replaced by the groups described above; in addition, one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups.
The heterocycloalkyl group used in the present invention means a monovalent functional group obtained by removing one hydrogen atom from a non-aromatic hydrocarbon having a atomic number of 3 to 40. At this time, one or more carbons, preferably 1 to 3 carbons, in the ring are substituted with a heteroatom such as N, O or S. As non-limiting examples thereof, there are tetrahydrofuranyl, tetrahydrothienyl, morpholinyl, piperazinyl, pyranyl, tetrahydropyranyl, and the like.
The alkoxy group used in the present invention means a monovalent functional group represented by RO-, and 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, cyclohexyloxy and the like.
Alkylthio as used in the present invention means R 0 s-is a monovalent functional group, wherein R0 is an alkyl group having 1 to 40 carbon atoms, and may have a linear, branched or cyclic structure. Non-limiting examples of such alkylthio groups include methylthio, ethylthio, n-propylthio, isopropylthio, t-butylthio, n-butylthio and the like.
The aryloxy group used in the present invention means a monovalent functional group represented by R 'O-and R' is an aryl group having 6 to 60 carbon atoms. As non-limiting examples of such aryloxy groups, there are phenoxy, naphthoxy, biphenyloxy, and the like.
As used herein, arylthio means a monovalent functional group represented by R 'S-wherein R' is an aryl group having 6 to 60 carbon atoms. As non-limiting examples of such arylthio groups, phenylthio, naphthylthio, biphenylthio and the like are mentioned.
"halogen" or "halogen atom" as used herein means a member selected from fluorine, chlorine, bromine or iodine.
The alkylsilyl group used in the present invention means a silyl group substituted with an alkyl group having 1 to 30 carbon atoms, and the number of carbon atoms constituting the alkylsilyl group is at least 3, and as non-limiting examples of the alkylsilyl group, there are trimethylsilyl group, triethylsilyl group and the like. Aryl silicon group refers to alkyl silicon group substituted with at least one aryl group having 6 to 60 carbon atoms, and examples of the alkyl silicon group include phenyl dimethyl silicon group, naphthyl dimethyl silicon group, phenyl diethyl silicon group, diphenyl methyl silicon group, diphenyl ethyl silicon group, triphenyl silicon group, and the like.
The arylalkyl group of the present invention means an alkyl group in which at least one hydrogen atom of a linear or branched saturated hydrocarbon having from 1 to 30 carbon atoms is substituted with an aryl group having from 6 to 60 carbon atoms, and as a non-limiting example, phenylmethyl group, diphenylmethyl group, triphenylmethyl group, 2-phenylethyl group, 3-phenylpropyl group and the like can be mentioned.
The alkylaryl group of the present invention means an aryl group in which at least one hydrogen atom of an aryl group having from 6 to 60 carbon atoms is substituted with a linear or branched saturated hydrocarbon having from 1 to 30 carbon atoms, and as a non-limiting example, methylphenyl, dimethylphenyl, trimethylphenyl, tert-butylphenyl, isopropylphenyl and the like can be mentioned.
The alkylamino group used in the present invention means an amino group substituted with an alkyl group having 1 to 40 carbon atoms or a secondary amino group substituted with two alkyl groups having 1 to 40 carbon atoms, and as non-limiting examples of the alkylamino group, there are methylamino group, dimethylamino group, ethylamino group, diethylamino group and the like.
As the arylamine group used in the present invention, an amino group substituted with an aryl group having 6 to 60 carbon atoms, a secondary amine group substituted with two aryl groups having 6 to 60 carbon atoms, or a secondary amine group substituted with an alkyl group having 1 to 40 carbon atoms and an aryl group having 6 to 60 carbon atoms is mentioned, and as non-limiting examples of the arylamine group, an anilino group, a diphenylamino group, a 1-naphthylamino group, a 2-naphthylamino group, an N-phenylnaphthalene-1-amino group, a carbazolyl group, a phenoxazinyl group and the like are mentioned.
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 heterocyclic ring.
In the present invention, a five-membered heterocyclic ring refers to a five-membered heteroaromatic ring containing at least two carbon atoms, such as, by way of non-limiting example: furan, thiophene, pyrrole, imidazole, benzofuran, benzothiophene, indole, and the like. Six-membered carbocyclic ring refers to a six-membered hydrocarbon ring or six-membered aromatic ring containing at least two carbon atoms, as non-limiting examples, for example: cyclohexane, cyclohexene, benzene, naphthalene, phenanthrene, and the like. Six-membered heterocyclic ring refers to a six-membered heterocyclic ring or six-membered heteroaromatic ring containing at least two carbon atoms, as non-limiting examples, for example: pyran, piperidine, pyridine, piperazine, pyrazine, and the like.
Further, the anthracene derivative is selected from the group consisting of:
wherein G is selected from O, S, SO, SO 2 、NAr 3 ；
Ar 3 Selected from hydrogen, substituted or unsubstituted C 6 ～C 60 Aryl, substituted or unsubstituted C 6 ～C 60 Arylamine group, substituted or unsubstituted C 2 ～C 60 Heteroaryl groups.
Further, the R 1 、R 2 、R 3 、R 4 Each independently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted C 1 ～C 30 Alkyl, substituted or unsubstituted C 3 ～C 30 Cycloalkyl, substituted or unsubstituted C 6 ～C 60 Aryl, substituted or unsubstituted C 2 ～C 60 Heteroaryl, substituted or unsubstituted C 1 ～C 30 Alkoxy, substituted or unsubstituted C 6 ～C 60 Arylamine groups.
Further, the Ar 1 、Ar 2 、Ar 3 Each independently selected from the group consisting of hydrogen, substituted or unsubstituted C 6 ～C 60 Aryl, substituted or unsubstituted C 6 ～C 60 Arylamine group, substituted or unsubstituted C 2 ～C 60 Heteroaryl groups.
Further, the heteroaryl or the heterocyclic aryl is a group consisting of groups shown as II-1 to II-17, and the specific structures of II-1 to II-17 are as follows:
wherein Z is 1 、Z 2 Each independently selected from the group consisting of hydrogen, deuterium, halogen, hydroxy, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxyl or carboxylate thereof, sulfonic acid or sulfonate thereof, phosphoric acid or phosphate thereof, C 1 -C 40 Alkyl, C 2 -C 40 Alkenyl, C 2 -C 40 Alkynyl, C 1 -C 40 Alkoxy, C 3 -C 40 Naphthene radical, C 3 -C 40 Cycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Aryl sulfide group, or substituted or unsubstituted C 2 -C 60 Heteroaryl groups;
x1 represents an integer of 1 to 4; x2 represents an integer of 1 to 3; x3 represents 1 or 2; x4 represents an integer of 1 to 6; x5 represents an integer of 1 to 5;
t1 represents an oxygen atom or a sulfur atom;
represents the bond between the substituent and the main structure.
Substituted C as described in the present invention 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Aryl sulfide group, substituted C 2 -C 60 The substituent is selected from hydrogen, deuterium, halogen, hydroxy, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxyl or carboxylate, sulfonic acid or sulfonate, phosphoric acid or phosphate, C 1 -C 40 Alkyl, C 2 -C 40 Alkenyl, C 2 -C 40 Alkynyl, C 1 -C 40 Alkoxy, C 3 -C 40 Naphthene radical, C 3 -C 40 Cycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy groupRadical, C 6 -C 60 Aryl sulfide group, or C 2 -C 60 A heterocyclic aryl group.
As used herein, "combination" or "group" means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that one of ordinary skill in the art can contemplate from the applicable list. For example, alkyl and deuterium can combine to form a partially or fully deuterated alkyl group; halogen and alkyl groups may combine to form haloalkyl substituents such as trifluoromethyl and the like; and halogen, alkyl and aryl may combine to form a haloaralkyl.
Further, the anthracene derivative is one of the following structures B751-B879:
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wherein hydrogen atoms in the structure may be partially or fully replaced by deuterium atoms.
An organic electroluminescent material comprising the anthracene derivative containing a plurality of boron atoms.
The organic electroluminescent material may be constituted by using the compound of the present invention alone or may contain other compounds at the same time.
The compound of the present invention contained in the organic electroluminescent material of the present invention can be used as, but is not limited to, a light-emitting layer material.
An organic electroluminescent device comprising a first electrode, a second electrode and at least one organic layer disposed between the first electrode and the second electrode, the organic layer comprising the anthracene derivative provided by the present invention.
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 further 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-generating layers. An intermediate layer having, for example, an exciton blocking function can likewise be introduced between the two light-emitting layers. It should be noted, however, that not every one of these layers need be present. The organic electroluminescent device described herein may comprise one light emitting layer, or it may comprise a plurality of light emitting layers. I.e. a plurality of luminescent compounds capable of emitting light are used in the luminescent layer. A system with three light emitting layers is preferred, wherein the three layers can display blue, green and red light emission. If more than one light-emitting layer is present, at least one of these layers comprises a compound of the invention according to the invention.
Further, the organic electroluminescent device according to the present invention does not comprise a separate hole injection layer and/or hole transport layer and/or hole blocking layer and/or electron transport layer, i.e. the light emitting layer is directly adjacent to the hole injection layer or anode and/or the light emitting layer is directly adjacent to the electron transport layer or electron injection layer or cathode.
In the other layers of the organic electroluminescent device according to the invention, in particular in the hole injection and hole transport layers and in the electron injection and electron transport layers, all materials can be used in the manner generally used according to the prior art. A person of ordinary skill in the art will thus be able to use all materials known in relation to organic electroluminescent elements in combination with the light-emitting layer according to the invention without inventive effort.
Furthermore, organic electroluminescent devices are preferred, which apply one or more layers by means of sublimation methods, wherein the sublimation is performed in a vacuum at less than 10 -5 Pa, preferably below 10 -6 The material is applied by vapor deposition at an initial pressure of Pa. However, the initial pressure may also be even lower, for example below 10 -7 Pa。
Preference is likewise given to organic electroluminescent devices which apply one or more layers by means of an organic vapor deposition process or by means of carrier gas sublimation, where at 10 -5 The material is applied at a pressure between Pa and 1 Pa. A particular example of this method is the organic vapor jet printing method, wherein the material is applied directly through a nozzle and is thus structured.
Furthermore, organic electroluminescent devices are preferred in which one or more layers are produced from a solution, for example by spin coating, or by means of any desired printing method, for example screen printing, flexography, lithography, photoinitiated thermal imaging, thermal transfer, inkjet printing or nozzle printing. Soluble compounds the soluble compounds are obtained, for example, by suitable substitution of the compounds of formula (I). These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, a hybrid method is possible, in which one or more layers are applied, for example from a solution, and one or more further layers are applied by vapor deposition.
These methods are generally known to those of ordinary skill in the art and they can be applied to the organic electroluminescent element comprising the compound according to the present invention without inventive effort.
The invention therefore also relates to a method for manufacturing an organic electroluminescent device according to the invention, which applies at least one layer by means of a sublimation method and/or at least one layer by means of an organic vapour deposition method or by means of carrier gas sublimation and/or at least one layer from a solution by spin coating or by means of a printing method.
Furthermore, the present invention relates to a pharmaceutical composition comprising at least one compound of the invention as indicated above. The same preferences as indicated above in relation to the organic electroluminescent device apply to the compounds of the invention. In particular, the compounds may furthermore preferably comprise further compounds. Treatment of the compounds of the invention from the liquid phase, for example by spin coating or by printing methods, requires treatment of the formulations of the compounds of the invention. These formulations may be, for example, solutions, dispersions or emulsions. For this purpose, it may be preferable to use a mixture of two or more solvents. 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, (-) -fenchyl, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3, 4-dimethylbenzene, 3, 5-dimethylbenzene, acetophenone, alpha-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, 1-methylpyrrolidone, p-cymene, phenetole, 1, 4-diisopropylbenzene, dibenzyl ether, diethylene glycol methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol, triethylene glycol, 1, 2-dimethyl benzene ether, 1-dimethyl-n-butyl ether, 1-dimethyl-butyl benzene, 1-dimethyl-n-butyl benzene, 1-dimethyl-butyl benzene, n-butyl benzene, dimethyl benzene, n-butyl benzene, dimethyl benzene, or a mixture of these solvents.
Further, 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.
Further, the light-emitting layer contains the anthracene derivative of the present invention.
Further, the light-emitting layer comprises a dopant and a light-emitting host, wherein the host comprises a light-emitting host selected from the group consisting of anthracene, naphthalene, anthracene, pyrene, perylene, phenanthrene, fluoranthene,Benzanthracene, fluorene, spirofluorene and pentacene and derivatives thereof; the dopant comprises the anthracene derivative of the present invention.
Further, the mass ratio of the dopant to the light-emitting main body is 1:99-50:50.
A consumer product made from the organic electroluminescent device, the consumer product comprising the organic electroluminescent device provided by the invention.
The consumer product described in the present invention may be one of the following products: flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, laser printers, telephones, cellular telephones, tablet computers, tablet handsets, personal Digital Assistants (PDAs), wearable devices, laptop computers, digital cameras, video cameras, viewfinders, micro-displays with a diagonal of less than 2 inches, 3-D displays, virtual reality or augmented reality displays, vehicles, video walls comprising a plurality of displays tiled together, theatre or gym screens, phototherapy devices, and billboards.
Unless otherwise indicated, all starting materials used in the present invention are commercially available, and any ranges recited herein include any number between the endpoints and any subrange formed by any number between the endpoints or any number between the endpoints.
Compared with the prior art, the invention has the beneficial effects that:
the anthracene derivative provided by the invention is provided with a novel organic electroluminescent compound with a large plane conjugated structure formed by anthracene and seven-membered ring, and the seven-membered ring anthracene derivative realizes HOMO and LUMO separation through the resonance effect between boron and nitrogen, so that the Thermal Activation Delayed Fluorescence (TADF) effect is realized, and the light-emitting wavelength is shorter than that of the existing compound; thereby improving the efficiency and lifetime of an organic electroluminescent device comprising the compound; in addition, the compound improves the solubility in a solution to solve the problems of productivity and cost of the process of the conventional blue light material, and can be used for preparing a light-emitting layer not in the vapor deposition process but in the solution process in the original process.
Drawings
In order to more clearly illustrate the embodiments of the invention or the technical solutions in the prior art, the drawings that are required in the embodiments or the description of the prior art will be briefly described, it being obvious that the drawings in the following description are only some embodiments of the invention, and that other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
Fig. 1 shows a schematic diagram of an organic light emitting device 100. The illustrations are not necessarily drawn to scale. The 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. The device 100 may be fabricated by sequentially depositing the layers described.
Fig. 2 shows a schematic diagram of an organic light emitting device 200 with 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 emissive layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second emissive layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. The device 200 may be prepared by sequentially depositing the layers described. Because the most common OLED device has one light emitting layer, and device 200 has a first light emitting layer and a second light emitting layer, the light emitting peaks of the first and second light emitting layers may be overlapping or cross-overlapping or non-overlapping. In the corresponding layers of device 200, materials similar to those described with respect to device 100 may be used. Fig. 2 provides one example of how some layers may be added from the structure of the device 100.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be described in detail below. It will be apparent that the described embodiments are only some, but not all, embodiments of the invention. All other embodiments, based on the examples herein, which are within the scope of the invention as defined by the claims, will be within the scope of the invention as defined by the claims.
In the invention, the preparation methods are all conventional methods unless otherwise specified. All materials used, unless otherwise indicated, are commercially available from the disclosure and percentages such as percentages by mass unless otherwise indicated. The novel series of organic compounds provided by the present invention, all of which are carried out under well known suitable conditions, involve some simple organic preparation, for example the preparation of N, N-diphenylamine derivatives, can be synthesized by skilled manipulation techniques and are not described in detail in the present invention.
The following examples are examples of the test apparatus and method for testing the performance of OLED materials and devices as follows:
OLED element performance detection conditions:
luminance and chromaticity coordinates: photoresearch PR-715 was tested using a spectrum scanner;
Current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: using the NEWPORT 1931-C test;
life test: LTS-1004AC life test apparatus was used.
Example 1
A process for the preparation of compound B751 comprising the steps of:
the first step: preparation of compound int.—1
Under the protection of nitrogen, 50.0mmol of o-iodobromobenzene is dissolved in 100mL of dry tetrahydrofuran, the temperature is reduced to 0 ℃, 52.0mL of 1M isopropyl magnesium bromide THF solution is added dropwise, stirring reaction is carried out for 1 hour, 48.0mmol of 9H-tribenzo [ a, c, e ] [7] cycloretainer-9-ketone (CAS: 68089-73-6) dissolved in THF is added dropwise, stirring reaction is carried out for 2 hours at room temperature, 50mL of 2M diluted hydrochloric acid aqueous solution is added, extraction is carried out by ethyl acetate, organic phase is collected, drying, filtration and reduced pressure concentration and drying are carried out on filtrate, and intermediate Int-1 is obtained after separation and purification by a silica gel column, and the yield is 94%.
And a second step of: preparation of compound int-2
Under the protection of nitrogen, 40.0mmol of Int. -1 prepared in the first step is dissolved in 100mL of dichloromethane, 80.0mmol of triethylsilane is added, the temperature is reduced to 0 ℃, 30mL of trifluoroacetic acid is slowly added dropwise, the temperature is raised to room temperature, stirring is carried out for 12 hours, 50mL of water is added, dichloromethane is used for extraction, an organic phase is collected for drying, filtering, the filtrate is concentrated and dried under reduced pressure, and the Int. -2 is obtained by separating and purifying by a silica gel column, wherein the yield is 82%.
And a third step of: preparation of compound int.—3
Dissolving 50.0mmol of the intermediate Int < -2 > prepared in the second step in 120mL of dry THF, cooling to-78 ℃ under the protection of nitrogen, dropwise adding 22.0mL of 2.5M n-butyllithium n-hexane solution, stirring for reaction for 1 hour, dropwise adding 75.0mmol of DMF, heating to room temperature, stirring for reaction for 1 hour, adding 50mL of 2M dilute hydrochloric acid aqueous solution, separating an organic phase, extracting the aqueous phase with dichloromethane, collecting an organic phase, drying and filtering, concentrating and drying the filtrate under reduced pressure, separating and purifying by a silica gel column to obtain Int < -3 >, and obtaining the yield of 87%.
Fourth step: preparation of compound int.—4
Under the protection of nitrogen, 40.0mmol of intermediate int-3 is dissolved in 80mL of dichloromethane, 8.0mmol of boron trifluoride diethyl etherate solution is added, stirring reaction is carried out for 1 hour at room temperature, decompression concentration and drying are carried out, silica gel column separation and purification are carried out, and intermediate int-4 is obtained, and the yield is 92%.
Fifth step: preparation of compound int.—5
41.2mmol of intermediate Int.-4 is dissolved in 120mL of dichloromethane, the temperature is reduced to 0 ℃ by an ice-water bath, 4.1mmol of p-toluenesulfonic acid is added, 42.0mmol of NBS is added in portions, the mixture is stirred and reacted for 2 hours, 100mL of 10% sodium bicarbonate aqueous solution is added, an organic phase is separated, water washing is carried out, the organic phase is collected, drying and filtration are carried out, the filtrate is concentrated and dried under reduced pressure, and the compound Int. -5 is obtained by separating and purifying by a silica gel column, and the yield is 96%.
Sixth step: preparation of compound int.—6
Under the protection of nitrogen, 20.0mmol of intermediate Int-5 is dissolved in 60mL of dry THF, 24.0mmol of triisopropyl borate is added, the temperature is reduced to-100 ℃, 24.0mmol of 2.5M n-butyllithium n-hexane solution is added dropwise, the reaction is stirred for 1 hour, the temperature is raised to room temperature, 50mL of 2M dilute hydrochloric acid aqueous solution is added dropwise, an organic phase is separated, the aqueous phase is extracted by ethyl acetate, the organic phase is collected, dried, filtered, the filtrate is concentrated to dryness under reduced pressure, petroleum ether is added for dispersion, the filter cake is washed by petroleum ether, and the compound Int-6, yellow solid is obtained with the yield of 78%.
Seventh step: preparation of compound int-7
20.0mmol of intermediate int.-6 is dispersed in 100mL of dry toluene, 40.0mmol of o-phenylenediamine, 22.0mmol of p-toluenesulfonic acid and 2.0mmol of anhydrous magnesium sulfate are added, the mixture is heated to reflux and stirred for reaction for 24 hours, the mixture is cooled to room temperature, filtered, the filtrate is concentrated to dryness under reduced pressure, and the compound int.-7 is obtained by separating and purifying with a silica gel column, and is a yellow solid with the yield of 67%.
Eighth step: preparation of Compound B751
Dispersing 10.0mmol of intermediate Int. -7 in 50mL of dry o-dichlorobenzene under the protection of nitrogen, adding 25.0mmol of boron tribromide, heating to reflux, stirring and reacting for 24 hours, cooling to room temperature, adding 75.0mmol of 1M 2,4, 6-trimethylphenylmagnesium bromide toluene/THF solution, stirring and reacting for 6 hours at room temperature, adding 50mL of water, separating an organic phase, extracting the aqueous phase with dichloromethane, collecting the organic phase, drying, filtering, concentrating the filtrate under reduced pressure, separating and purifying by a silica gel column to obtain a compound B751 as a yellow solid, wherein the yield is 30 percent, 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)。
Example 2
The preparation method of the compound B757 and the compound B759 comprises the following steps:
the first step: preparation of compound int.—8
Referring to the synthesis of the seventh step of example 1, only the o-phenylenediamine of the seventh step of example 1 was replaced with sub-1 (prepared by the synthesis method disclosed in reference to patent CN114560872 a), compound int.—8 was prepared in a yield of 64%.
And a second step of: preparation of Compound B757 and Compound B759
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Dispersing 10.0mmol of intermediate Int. -8 in 50mL of dry o-dichlorobenzene under the protection of nitrogen, adding 25.0mmol of boron tribromide, heating to reflux, stirring and reacting for 24 hours, cooling to room temperature, adding 75.0mmol of 1M 2,4, 6-trimethylphenylmagnesium bromide toluene/THF solution, stirring and reacting for 15 hours at room temperature, adding 50mL of water, separating an organic phase, extracting the aqueous phase with dichloromethane, collecting the organic phase, drying, filtering, concentrating the filtrate under reduced pressure, separating and purifying by a silica gel column to obtain a compound B757, yellow solid, yield of 24%, HRMS (ESI) M/z 979.5079[ M+H ]] + ， 1 HNMR(δ、CDCl 3 ): 8.43 to 8.38 (4H, m); 8.18 to 8.15 (1H, m); 8.09 to 8.03 (4H, m); 7.63 to 7.61 (1H, d); 7.54 to 7.46 (5H, m); 7.37 to 7.32 (2H, m); 7.28 to 7.23 (2H, m); 7.20 to 7.19 (1H, d); 7.12 (1H, s); 7.04 to 7.02 (4H, m); 2.37 (12H, s); 2.18 (6H, s); 1.42 (9H, s); 1.29 (9H, s); compound B759 is obtained as a yellow solid in 9% yield, HRMS (ESI) m/z 979.5075[ M+H ] ] + ， 1 HNMR(δ、CDCl 3 )：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)。
Examples 3 to 128
Referring to the synthetic methods analogous to example 1 and example 2 above, the following compounds were prepared:
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application examples 1 to 129
As shown in fig. 1, an OLED element 100 of the present embodiment is a top-emission light element, and includes 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 element of the hole blocking layer 107, and the preparation method comprises the following steps:
1) The glass substrate coated with the ITO conductive layer is subjected to ultrasonic treatment in a cleaning agent for 30 minutes, rinsed in deionized water, subjected to ultrasonic treatment in an acetone/ethanol mixed solvent for 30 minutes, baked in a clean environment until completely dried, irradiated by an ultraviolet light cleaning machine for 10 minutes, and bombarded on the surface by a low-energy cation beam.
2) Placing the above ITO glass substrate in a vacuum chamber, and vacuumizing to less than 1×10- 5 Pa, silver is deposited on the ITO film as anode 102, and the thickness of deposited film isContinuing to evaporate the compounds DNTPD and F4TCNQ as the hole injection layer 103, wherein F4TCNQ is 3% of DNTPD by mass, and the evaporation film thickness is +. >Continuously evaporating NPD as hole transport layer 104 on the hole injection layer film, and evaporating to obtain a film thickness of +.>
3) Continuing to vapor deposit a layer of compound HT202 as an electric current on the hole transport layerA sub-barrier layer 105 having a vapor deposition film thickness of
4) Continuously evaporating a layer of anthracene derivative shown in the formula (I) and BH017 serving as an organic light-emitting layer 106 on the electron blocking layer, wherein BH017 is a host material, the anthracene derivative shown in the formula (I) is a doping material, the doping concentration of the anthracene derivative shown in the formula (I) in BH017 is 5%, and the evaporation film thickness is
5) Evaporating a layer of compound LiQ and ET205 as electron transport layer 108 of device on the light emitting layer, wherein the mass ratio of LiQ and ET205 is 1:1, and the film thickness of the evaporated film is
6) Further evaporating an electron injection layer 109 of compound LiF as device on the electron transport layer to obtain an evaporated film thickness of
7) A transparent cathode 110 for evaporating metal magnesium and silver on the electron injection layer as elements, wherein the mass ratio of magnesium to silver is 2:1, and the film thickness of the evaporated film is
Finally, a layer of compound NPD was deposited as a capping layer 111 on top of the transparent cathode, with a deposition film thickness of 500A.
The structures of the compounds used in the examples above were as follows:
Application example 130
An organic electroluminescent device 200 is a top-emission multi-luminescent layer device, the structure of which is shown in fig. 2, and the device comprises a substrate 201, an anode 202, a hole injection layer 203, a hole transport layer 204, a first luminescent layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second luminescent layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. The element can be prepared by sequentially depositing the layers described.
Since the most common organic electroluminescent device has one single color light emitting layer or three light emitting layers of three primary colors, and the element shown in fig. 2 has two light emitting layers of the same color, the element may have the light emitting peak shapes of the first light emitting layer and the second light emitting layer overlapping or intersecting or non-overlapping. In the corresponding layers of the element shown in fig. 2, materials similar to those described in connection with the element shown in fig. 1 may be used. Fig. 2 provides one example of how layers may be added from the structure in the element shown in fig. 1. The specific preparation method is the same as that of the OLED element shown in FIG. 1. The simple layered structure illustrated in fig. 1 and 2 is provided as a non-limiting example, and it should be understood that embodiments of the present invention may be used in conjunction with a wide variety of other structures. The particular materials and structures described are exemplary in nature, and other materials and structures may be used. Functional OLEDs may be implemented by combining the various layers described in different ways based on design, performance, and cost factors, or several layers may be omitted entirely. 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 mixtures of host and dopant, or more generally, mixtures. Also, the layers may have various sublayers. The names given to the various layers herein are not intended to be strictly limiting. For example, in the element shown in fig. 2, the hole transporting layer 204 transports holes and injects holes into the first light emitting layer 205, and may be described as a hole transporting layer or an electron blocking layer. In one embodiment, an OLED may be described as having an organic layer disposed between a cathode and an anode. This organic layer may comprise a single layer or may further comprise multiple layers of different organic materials as described in fig. 1 and 2.
The specific preparation method is the same as that of the OLED element described in application example 1.
Comparative example 1
The same procedure as in application example 1 was followed except that compound B3N was used instead of the anthracene derivative represented by formula (I). The structure of compound B3N is:
the organic electroluminescent element prepared by the above process was subjected to the following performance test:
the driving voltage and current efficiency and the lifetime 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 0.1V per second, and it was determined that the current density of the organic electroluminescent element reached 10mA/cm 2 The voltage at the time is the driving voltage, and the brightness at the time is measured; the ratio of brightness to current density is the current efficiency; LT95% life test is as follows: at 1000cd/m using a luminance meter 2 The luminance decay of the organic electroluminescent element was measured to be 950cd/m while maintaining a constant current at luminance 2 Time in hours. The data listed in table 2 are relative data compared to comparative example element 1.
TABLE 2
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As can be seen from Table 2, the anthracene derivative of the present invention as a blue light doped material obtained a deep blue light organic electroluminescent device having higher current efficiency, lower driving voltage, narrower full-height half-peak width of the light emission peak, and an initial luminance of the device of 1000cd/m, as compared with the organic electroluminescent device using B3N as a blue light doped material 2 The LT90% lifetime of the device is also greatly improved under the starting conditions of (a).
Compared with the compound B3N of the comparative example 1, the anthracene derivative of the invention is mainly characterized in that the conjugated area of the 9-phenylanthracene of the B3N serving as a donor part is small, and the donor part of the anthracene derivative of the invention is large plane conjugated of seven-membered ring anthracene, the conjugated area is increased, and the exciton transmission capability is enhanced, so that the TADF effect is realized under the action of boron-nitrogen atom resonance, the luminous efficiency is improved, and the excellent luminous performance is shown.
The organic electroluminescent device of the present invention can be applied to flat-panel light emitters such as wall-mounted televisions, flat-panel displays, and lighting, light sources such as copiers, printers, backlights for liquid crystal displays, and measuring instruments, display panels, and marker lamps.
The foregoing is merely illustrative of the present invention, and the present invention is not limited thereto, and any person skilled in the art will readily recognize that variations or substitutions are within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.

Claims (10)

1. An anthracene derivative is characterized in that the structural general formula of the anthracene derivative is shown as a formula (I):
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;
R 1 、R 2 、R 3 、R 4 each independently selected from the group consisting of hydrogen, deuterium, halogen atoms, cyano groups, substituted or unsubstituted C 1 ～C 30 Alkyl, substituted or unsubstituted C 1 ～C 30 Heteroalkyl, substituted or unsubstituted C 3 ～C 30 Cycloalkyl, substituted or unsubstituted C 6 ～C 60 Aryl, substituted or unsubstituted C 2 ～C 60 Heteroaryl, substituted or unsubstituted C 1 ～C 30 Alkoxy, substituted or unsubstituted C 6 ～C 60 Aryloxy, substituted or unsubstituted C 1 ～C 30 Alkylthio, substituted or unsubstituted C 6 ～C 60 Arylthio, substituted or unsubstituted C 1 ～C 30 Alkylamino, substituted or unsubstituted C 6 ～C 60 Arylamine group, substituted or unsubstituted C 1 ～C 30 Alkylsilyl, substituted or unsubstituted C 6 ～C 60 Arylsilyl, substituted or unsubstituted C 2 ～C 30 Alkenyl, or substituted or unsubstituted C 2 ～C 30 Alkynyl groups;
Ar 1 、Ar 2 each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C 6 ～C 60 Aryl, substituted or unsubstituted C 6 ～C 60 Arylamine group, substituted or unsubstituted C 2 ～C 60 Heteroaryl groups;
R 1 、R 2 、R 3 、R 4 each independently represents one or more to saturated substitutions.
2. The anthracene derivative according to claim 1, wherein the anthracene derivative is selected from the group consisting of:
wherein G is selected from O, S, SO, SO 2 、NAr 3 ；
R 1 、R 2 、R 3 、R 4 Each independently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted C 1 ～C 30 Alkyl, substituted or unsubstituted C 3 ～C 30 Cycloalkyl, substituted or unsubstituted C 6 ～C 60 Aryl, substituted or unsubstituted C 2 ～C 60 Heteroaryl, substituted or unsubstituted C 1 ～C 30 Alkoxy, substituted or unsubstituted C 6 ～C 60 Arylamine groups;
Ar 1 、Ar 2 、Ar 3 each independently selected from the group consisting of hydrogen, substituted or unsubstituted C 6 ～C 60 Aryl, substituted or unsubstituted C 6 ～C 60 Arylamine group, substituted or unsubstituted C 2 ～C 60 Heteroaryl groups.
3. The anthracene derivative according to claim 1, wherein R is 1 ～R 4 Each is identically or differently selected from the group consisting of hydrogen, deuterium, cyano, methyl, ethyl, isopropyl, isobutyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted benzanthracenyl, substituted or unsubstituted pyrenyl A group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted carbazole groupA group consisting of a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, and a substituted or unsubstituted triazinyl group;
Ar 1 、Ar 2 each independently selected from the group consisting of substituted or unsubstituted: phenyl, naphthyl, anthryl, benzanthraceyl, phenanthryl, pyrenyl,A group, perylene group, fluoranthenyl group, naphthacene group, pentacene group, benzopyrene group, biphenyl group, terphenyl group, tripolyphenyl group, tetrabiphenyl group, fluorenyl group, spirobifluorenyl group, dihydrophenanthrene group, triphenylene group, dihydropyrenyl group, tetrahydropyrenyl group, cis-or trans-indenofluorenyl group, cis-or trans-indenocarbazolyl group, indolocarbazolyl group, benzofuranocarbazolyl group, benzothiophenocarbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, azadibenzo [ g, id]Naphtho [2,1,8-cde ]Diatom, trimeric indenyl, heterotrimeric indenyl, spirotrimeric indenyl, spiroheterotrimeric indenyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo [5,6 ]]Quinolinyl, benzo [6,7]Quinolinyl, benzo [7,8]Quinolinyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthamidinyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthazolyl, anthracnose oxazolyl, phenanthrooxazolyl, isoxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazabenzophenanthryl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl, 2, 7-diazapyrenyl, 2, 3-diazapyrenyl, 1, 6-diazapyrenylHeteropyrenyl, 1, 8-diazapyrenyl, 4,5,9, 10-tetraazaperylenyl, pyrazinyl, phenazinyl, phenoxazinyl, phenothiazinyl, fluoroerythronyl, naphthyridinyl, azacarbazolyl, benzocarboline yl, carboline yl, phenanthroline, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazole, 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-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2, 3-triazinyl, 1,2, 4-tetrazolyl, 1,2, 5-tetrazolyl, 1,2, 4-thiazinyl, 1,3, 2, 4-thiazolyl, a combination of these groups, or a group of groups derived from a purine, 4, 3, 4-diazolidinyl, or a combination of these groups.
4. An anthracene derivative according to any one of claims 1 to 3, wherein the anthracene derivative is one of the following structures B751 to B879:
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wherein hydrogen atoms in the structure may be partially or fully replaced by deuterium atoms.
5. An organic electroluminescent material, characterized in that the organic electroluminescent material comprises an anthracene derivative according to any one of claims 1 to 4.
6. An organic electroluminescent device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, the organic layer comprising the anthracene derivative according to any one of claims 1-4.
7. The organic electroluminescent device according to claim 6, wherein the organic layer is one or more selected from 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;
preferably, the light-emitting layer comprises the anthracene derivative according to any one of claims 1 to 4.
8. The organic electroluminescent device of claim 7, wherein the light-emitting layer comprises a dopant and a light-emitting host comprising a light-emitting host selected from the group consisting of anthracene, naphthalene, anthracene, pyrene, perylene, phenanthrene, fluoranthene, Benzanthracene, fluorene, spirofluorene and pentacene and derivatives thereof; the dopant comprising the anthracene derivative according to any one of claims 1 to 4.
9. The organic electroluminescent device of claim 8, wherein the mass ratio of dopant to light-emitting body is 1:99-50:50.
10. A consumer product comprising an organic electroluminescent device as claimed in any one of claims 6 to 9.
CN202310404690.6A 2023-04-17 2023-04-17 Anthracene derivative containing multiple boron atoms and application thereof Pending CN116715686A (en)

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