Organic electroluminescent compound and organic electroluminescent element comprising the same

Abstract

The present invention relates to an organic electroluminescent compound, a light-emitting device, and a consumer product, and an organic electroluminescent device having improved driving voltage and / or current efficiency characteristics can be provided by comprising the organic electroluminescent compound of the present disclosure.

Description

TECHNICAL FIELD

[0001] The present application belongs to the technical field of organic electroluminescence, and particularly relates to an organic electroluminescence compound, an organic electroluminescence material, a light-emitting device and a consumer product. BACKGROUND

[0002] The substances used in the organic electroluminescence element are mostly pure organic substances or organic metal complexes formed by complexing organic substances with metals, and can be classified into hole injectors, hole transporters, light-emitting substances, electron transporters, electron injectors, and the like according to the use. Here, as the hole injectors or hole transporters, organic substances having relatively small ionization energy are mainly used, and as the electron injectors or electron transporters, organic substances having relatively large electronegativity are mainly used. In addition, the substances used as the light-emitting auxiliary layer preferably satisfy the following characteristics.

[0003] First, the substances used in the organic electroluminescence element need to have good thermal stability, because the Joule heat occurs due to the migration of charges inside the organic electroluminescence element. At present, the glass transition temperature of the material commonly used as the hole transport layer is low, and thus the phenomenon of the decrease in the light-emitting efficiency due to the crystallization occurs when driven at a low temperature. Second, in order to reduce the driving voltage, the organic substance adjacent to the cathode and the anode needs to be designed to have a small charge injection barrier and a high charge mobility. Third, some charges are inevitably accumulated on the interface between the electrode and the organic layer and the interface between the organic layers due to the energy barrier, and thus a substance having excellent electrochemical stability is needed.

[0004] The light-emitting layer is composed of two substances, a host light-emitting substance and a dopant, and the dopant needs to have a high quantum efficiency, and the host light-emitting substance needs to have a large energy gap compared to the dopant and easily transfer energy to the dopant. The display for a television, a mobile device, and the like realizes full color according to the three primary colors of red, green, and blue, and the light-emitting layer is composed of a red host light-emitting substance / dopant, a green host light-emitting substance / dopant, and a blue host light-emitting substance / dopant, respectively. At present, the blue light material still has the problems of a low light-emitting quantum efficiency and a poor color purity. The main reason for this situation is that the blue light comes from the transition between energy levels having a wide energy gap, and there is a certain difficulty in designing the organic compound having a wide band gap, and secondly, there is a strong π-π bond interaction in the system of the blue light material, and there is a strong charge transfer characteristic, so that there are more non-radiative relaxation channels in the wide band gap, which exacerbates the fluorescence quenching between molecules, and reduces the quantum yield of the blue light system.

[0005] In view of the above reasons, the present application is proposed. SUMMARY

[0006] In order to solve the above problems existing in the prior art, the present application provides an organic electroluminescent compound, an organic electroluminescent material, a light-emitting device and a consumer product, wherein the organic electroluminescent compound is blue to deep blue and has high luminous efficiency.

[0007] The first object of the present application is to provide an organic electroluminescent compound.

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

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

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

[0011] In order to achieve the above objects, the present application adopts the following technical solutions.

[0012] An organic electroluminescent compound, wherein the structure general formula of the compound is shown as formula (I):

[0013]

[0014] wherein Ar 1 is selected from the group consisting of substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 arylamino, substituted or unsubstituted C2-C 60 heteroaryl;

[0015] X is selected from O, S, Se, CR 5 R 6 , SiR 5 R 6 , NR 5 or no X;

[0016] ring A, ring B are selected from the group consisting of substituted or unsubstituted C6-C 60 aromatic ring, substituted or unsubstituted C2-C 60 heteroaromatic ring;

[0017] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 are each independently selected from hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, C1-C 40 alkyl, c1-C 40 haloalkyl, C2-C 40 alkenyl, C2-C 40alkyl, C1-C 40 alkoxy, C1-C 40 alkylthio, C3-C 40 cycloalkyl, C3-C 40 cycloalkenyl, C3-C 40 heterocycloalkyl, C6-C 60 aryloxy, C6-C 60 arylthio, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C2-C 60 heteroaryl, tri(C1-C 40 alkylsilyl, tri(C6-C 60 arylsilyl, di(C1-C40)alkyl(C6-C 60 arylsilyl, C1-C 40 alkyldi(C6-C60)arylsilyl, C1-C 40 alkylcarbonyl, C1-C 40 alkoxycarbonyl, C6-C 60 arylcarbonyl, di(C6-C 60 arylborylcarbonyl, di(C1-C 40 alkylborylcarbonyl, C1-C 40 alkyl(C6-C 60 arylborylcarbonyl, C6-C 60 aryl(C1-C 40 alkyl, and C1-C 40 alkyl(C6-C 60 aryl; any two or more of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 may be arbitrarily annelated or fused to each other to form a substituted or unsubstituted ring;

[0018] R 1 , R 2 , R 3 , R 4 respectively represent one or more to saturation substitution;

[0019] the dotted line indicates that it can be connected or not connected.

[0020] The alkyl used in the present application means a monovalent functional group obtained by removing one hydrogen atom from a straight chain or branched chain saturated hydrocarbon having 1 to 40 carbon atoms. As non-limiting examples thereof, there are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, hexyl, etc.

[0021] The aryl group in the sense of the present invention contains 6 to 60 carbon atoms, the heteroaryl group contains 2 to 60 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and heteroatoms is at least 5; the heteroatom is preferably selected from N, O or S. At this point, two or more rings of the heteroaryl group can be attached to each other simply or in a condensed form, further, a form condensed with an aryl group can also be included. As non-limiting examples of aryl and heteroaryl groups, in particular, groups selected from the group consisting of phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, pyrenyl, anthracenyl, perylenyl, fluoranthenyl, naphthacene, pentaphene, benzopyrenyl, biphenyl, biphenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydophenanthryl, triphenylenyl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, cis- or trans-indenocarbazolyl, indolocarbazolyl, benzofuranocarbazolyl, benzothienocarbazolyl, benzocarbazolyl, dibenzocarbazolyl, azadibenz[g, Id]naphtho[2,1,8-cde]azulene, truxenyl, isotruxenyl, spirotruxenyl, spiroisotruxenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, pyridyl, quinolyl, isoquinolyl, acridyl, phenanthridyl, benzo[5,6]quinolyl, benzo[6,7]quinolyl, benzo[7,8]quinolyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, phenanthroimidazolyl, pyridimidazolyl, pyrazimidazolyl, quinoximidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthroxazolyl, phenanthroxazolyl, isoxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazatriphenylene, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazanthracenyl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperylenyl, pyrazinyl, phenoxazinyl, phenothiazinyl, fluoranthenyl, naphthidinyl, 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.

[0022] As used herein, "halogen" or "halo" means fluorine, chlorine, bromine, or iodine.

[0023] Further, the organic electroluminescent compound is selected from any one of the following structures:

[0024]

[0025]

[0026]

[0027] wherein each T is independently selected from O, S, Se, or NR5;

[0028] R 1 , R 2 , R 3 , R 4 , R 5 , X, Ar 1 are the same as defined above.

[0029] Further, the X is selected from O, S, or Se.

[0030] Further, the T is selected from O, S, or Se.

[0031] Further, the R 1 , R 2 , R 3 , R 4 are each the same or different selected from the group consisting of hydrogen, deuterium, fluorine, nitrile.

[0032] Further, the Ar 1 is selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted anthryl, substituted or unsubstituted benzanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted yl, substituted or unsubstituted perylenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted indolyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0033] According to an embodiment of the present application, the R 1 , R 2 are each independently selected from hydrogen or nitrile.

[0034] According to an embodiment of the present invention, the R 3 、R 4 are each independently selected from deuterium or nitrile.

[0035] According to an embodiment of the present invention, X is O.

[0036] According to an embodiment of the present invention, T is S.

[0037] The substituted aryl, substituted arylamine, substituted heteroaryl, etc. described in the present invention are each independently selected from at least one of the following groups: deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, C1-C 40 Alkyl, C1-C 40 Halogenated alkyl, C2-C 40 Alkenyl, C2-C 40 Alkynyl, C1-C 40 Alkoxy, C1-C 40 Alkylthio, C3-C 40 Cycloalkyl, C3-C 40 Cycloalkenyl, C3-C 40 Heterocycloalkyl, C6-C 60 Aryloxy, C6-C 60 Arylthio, unsubstituted or substituted with one or more C6-C 60 Aryl-substituted C2-C 60 Heteroaryl, unsubstituted or deuterated, one or more C1-C 40 Alkyl and one or more C2-C 60 At least one substituted C6-C 60 Aryl, tri(C1-C 40 ) alkylsilyl, tri(C6-C 60 )Arylsilyl, di(C1-C 40 ) alkyl (C6-C 60 )Arylsilyl, C1-C 40 Alkyl di(C6-C 60 )Arylsilyl, C1-C 40 Alkylcarbonyl, C1-C 40 Alkoxycarbonyl, C6-C 60 Arylcarbonyl, di(C6-C 60 ) aryl boron carbonyl, di(C1-C 40 )alkyl boron carbonyl, C1-C 40 Alkyl (C6-C 60 ) aryl boron carbonyl, C6-C 60 Aryl (C1-C 40 ) alkyl, and C1-C 40 Alkyl (C6-C60 aryl.

[0038] Heteroalkyl in the sense of the present application means that a hydrogen atom or -CH2- in an alkyl group is replaced by at least one heteroatom selected from the group consisting of halogen, nitrile, N, O, S or Si, as non-limiting examples, difluoromethyl, trifluoromethyl, trifluoroethyl, pentafluoroethyl, nitrile, acetonitrile, methoxymethyl, methoxyethyl, trimethylsilyl, triisopropylsilyl and the like. Haloalkyl means that a hydrogen atom in an alkyl group is replaced by a halogen moiety, as non-limiting examples, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, trifluoroethyl, pentafluoroethyl and the like.

[0039] Alkenyl or alkynyl in the sense of the present application contains at least two carbon atoms, as non-limiting examples, alkenyl or alkynyl is preferably considered to mean cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.

[0040] Alkoxy, alkylthio in the sense of the present application preferably means alkoxy or alkylthio having 1 to 40 carbon atoms, as non-limiting examples, methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, n-pentoxy, s-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexoxy, n-heptoxy, cycloheptoxy, n-octoxy, cyclooctoxy, 2-ethylhexoxy, pentafluoroethoxy and 2,2,2-trifluoroethoxy, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio, trifluoromethylthio, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2,2,2-trifluoroethylthio, vinyloxy, vinylthio, propenyloxy, propenylthio, butenylthio, butenyloxy, pentenyloxy, pentenylthio, cyclopentenyloxy, cyclopentenylthio, hexenyloxy, hexenylthio, cyclohexenyloxy, cyclohexenylthio, ethynyloxy, ethynylthio, propynyloxy, propynylthio, butynyloxy, butynylthio, pentynyloxy, pentynylthio, hexynyloxy, hexynylthio.

[0041] Generally, cycloalkyl, cycloalkenyl according to the present application can be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, wherein one or more -CH2- groups can be replaced by N, O or S to form heterocycloalkyl, heterocycloalkenyl, for example, one -CH2- group in cyclopentyl is replaced by O to form tetrahydrofuranyl, one -CH2- group in cyclohexyl is replaced by O to form tetrahydropyranyl and the like; furthermore, one or more hydrogen atoms can also be replaced by a deuterium atom, a halogen atom or a nitrile group.

[0042] The aryloxy used in the present application means a monovalent functional group represented by R'O-, wherein R' is an aryl group having 6 to 60 carbon atoms. As non-limiting examples of such aryloxy, there are phenoxy, naphthoxy, biphenyloxy, and the like.

[0043] The arylthio used in the present application 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, there are phenylthio, naphthylthio, biphenylthio, and the like.

[0044] The alkylsilyl used in the present application means a silyl group substituted with an alkyl group having 1 to 40 carbon atoms, and the number of carbon atoms constituting the alkylsilyl group is at least 3. As non-limiting examples of the alkylsilyl group, there are trimethylsilyl, triethylsilyl, and the like. The arylsilyl means an alkylsilyl group substituted with at least one aryl group having 6 to 60 carbon atoms. As non-limiting examples, there are phenyldimethylsilyl, naphthyldimethylsilyl, phenyldiethylsilyl, diphenylmethylsilyl, diphenylethylsilyl, triphenylsilyl, and the like.

[0045] The "alkylcarbonyl", "alkoxycarbonyl", "arylcarbonyl", "arylboronyl", "alkylboronyl" in the present application means a substituted carbonyl group (-COR*), wherein R* is preferably selected from the group consisting of alkyl, alkoxy, cycloalkyl, aryl, heteroaryl, arylboron, alkylboron.

[0046] The arylphosphine used in the present application means a diarylphosphine group substituted with an aryl group having 6 to 60 carbon atoms. As non-limiting examples of the arylphosphine, there are diphenylphosphine, di(4-trimethylsilylphenyl)phosphine, and the like. The aryloxyphosphine means a diarylphosphine group in which the phosphorus atom is oxidized to the highest valence state.

[0047] The arylboron used in the present application means a diarylboron group substituted with an aryl group having 6 to 60 carbon atoms. As non-limiting examples of the arylboron, there are diphenylboron, di(2,4,6-trimethylphenyl)boron, and the like. The alkylboron means a dialkylboron group substituted with an alkyl group having 1 to 40 carbon atoms. As non-limiting examples of the alkylboron, there are di-tert-butylboron, di-isobutylboron, and the like.

[0048] The arylalkyl according to the present application means an alkyl group in which at least one hydrogen atom of a straight chain or branched chain saturated hydrocarbon having 1 to 40 carbon atoms is substituted with an aryl group having 6 to 60 carbon atoms. As non-limiting examples, there are phenylmethyl, diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl, and the like.

[0049] The alkyl group according to the present application means an alkyl group in which at least one hydrogen atom of an aromatic group having 6 to 60 carbon atoms is substituted with a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, and as non-limiting examples, there can be mentioned methylphenyl, dimethylphenyl, trimethylphenyl, t-butylphenyl, isopropylphenyl, and the like.

[0050] The aromatic ring in the present application means an aromatic hydrocarbon having 6 to 60 carbon atoms, and as non-limiting examples thereof, there can be mentioned benzene, naphthalene, phenanthrene, anthracene, pyrene, chrysene, perylene, coronene, and the like. The heteroaromatic ring in the present application means a heteroaromatic hydrocarbon having 2 to 60 carbon atoms, and as non-limiting examples thereof, there can be mentioned pyridine, quinoline, isoquinoline, carboline, pyrimidine, 1,3,5-triazine, furan, thiophene, pyrrole, and the like.

[0051] The heteroaromatic ring in the present application means a heteroaromatic hydrocarbon having 2 to 60 carbon atoms, and as non-limiting examples thereof, there can be mentioned pyridine, quinoline, isoquinoline, carboline, pyrimidine, 1,3,5-triazine, furan, thiophene, pyrrole, and the like.

[0052] Further, the compound is selected from one of the following structures of CJHB950 to CJHB1090:

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059] In each of the above structures, hydrogen atoms can be partially or entirely replaced with deuterium.

[0060] As used herein, "combination thereof' 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 would envision from the applicable list. For example, alkyl groups and deuterium atoms can be combined to form partially or fully deuterated alkyl groups; halogens and alkyl groups can be combined to form haloalkyl substituents, such as trifluoromethyl and the like; and halogens, alkyl groups, and aryl groups can be combined to form haloaralkyl groups.

[0061] An organic electroluminescent material includes the organic electroluminescent compound.

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

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

[0064] 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, wherein the organic layer comprises the organic electroluminescent compound according to the present application.

[0065] The organic electroluminescent device comprises a cathode, an anode, and at least one light-emitting layer. In addition to these layers, it can 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 generation layers. An intermediate layer having, for example, an exciton blocking function can likewise be introduced between two light-emitting layers. It should be noted, however, that not all of these layers need necessarily be present. The organic electroluminescent device described here can comprise one light-emitting layer, or it can comprise a plurality of light-emitting layers. A plurality of light-emitting compounds capable of emitting light are used in the light-emitting layers. Preference is given to a system having three light-emitting layers, wherein the three layers can exhibit blue, green and red electroluminescence. If more than one light-emitting layer is present, at least one of the layers comprises a compound according to the present application in accordance with the present application.

[0066] Further, the organic electroluminescent device according to the present application 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 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 further layers of the organic electroluminescent device according to the present application, 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. The person of ordinary skill in the art will thus be able to use in combination with the light-emitting layers according to the present application all materials known for organic electroluminescent elements without inventive step.

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

[0069] Likewise preferred is an organic electroluminescent device, which is applied by means of an organic vapour phase deposition method or by means of carrier gas sublimation of one or more layers, wherein the material is applied at a pressure of 10 -5 The method is a particular example of an organic vapour jet printing method, wherein the material is applied directly through a nozzle and is thus structured.

[0070] Further preferred is an organic electroluminescent device, which is produced from solution, for example by spin coating, or by means of any desired printing method, such as screen printing, flexographic printing, offset printing, light-induced thermal imaging, thermal transfer, inkjet printing or nozzle printing, of one or more layers. Soluble compounds, for example compounds of the formula I, are obtained by suitable substitution. These methods are also particularly suitable for oligomers, dendrimers and polymers. Further possible is a hybrid method, wherein one or more layers are applied, for example, from solution and one or more further layers are applied by vapour deposition.

[0071] These methods are generally known to the person of ordinary skill in the art and he can apply them without inventive labour to organic electroluminescent elements comprising the compounds according to the application.

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

[0073] Further, the present application relates to a compound of the present application comprising at least one compound of the present application as indicated above. The same preferences as indicated above with respect to the organic electroluminescence device apply to the compound of the present application. In particular, the compound can further comprise preferably further compounds. Formulations of the compounds according to the present application are required for processing the compounds according to the present application from the liquid phase, for example by spin coating or by printing methods. These formulations can be, for example, solutions, dispersions or emulsions. For this purpose, mixtures of two or more solvents can be preferably 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 -methyl naphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methyl anisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, 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, benzyl 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-isopropyl naphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1 -bis(3,4-dimethylphenyl)ethane, or mixtures of these solvents.

[0074] Further, the organic layer is selected from one or several 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] Further, the electron transport layer, the light emitting layer comprises an organic electroluminescence compound of the present application.

[0076] Further, the light emitting layer comprises a dopant and a light emitting host, the dopant comprising a compound selected from the group consisting of anthracene, naphthalene, anthracene, pyrene, perylene, phenanthrene, fluoranthene, In addition to the above, as the dopant material, a pyrene derivative having a pyrene skeleton in the molecule, a heterocyclic compound having an indole ring as a partial structure of a condensed ring, a heterocyclic compound having a carbazole ring as a partial structure of a condensed ring, a carbazole derivative, a thiazole derivative, a benzimidazole derivative, a polydialkyfluorene derivative, quinacridone, coumarin, rubrene, perylene and derivatives thereof, a benzopyran derivative, indenophenanthrene derivative, rhodamine derivative, aminostyryl derivative, and the like can be used. They can be used as a single layer formed alone, as a single layer formed by mixing with other materials, or as a stacked structure between layers formed alone, between layers formed by mixing, or between a layer formed alone and a layer formed by mixing.

[0077] In addition, a phosphorescent emitter can also be used as the dopant. As the phosphorescent emitter, a phosphorescent emitter of a metal complex of iridium, platinum, or the like can be used. A green phosphorescent emitter such as Ir(ppy)3, a blue phosphorescent emitter such as Firpic, Fir6, a red phosphorescent emitter such as Btp2lr(acac), and the like can be used, and as the host material at this time, the organic electroluminescent compound of the present application is preferably used. In addition, as the host material for hole injection and transport, a carbazole derivative such as 4,4'-bis(N-carbazolyl)biphenyl (CBP), TCTA, Mcp, and the like can be used. As the host material for electron transport, a compound such as p-bis(triphenylsilyl)benzene (UGH2), 2,2',2"-(l,3,5-phenylene)-tris(l-phenyl-lH-benzimidazole) (TPBI), and the like can be used, and a high-performance light-emitting element can be produced.

[0078] As for doping of a phosphorescent light-emitting material into a host material, in order to avoid concentration quenching, doping is preferably performed by co-evaporation in a range of 1 to 10% by mass with respect to the entire light-emitting layer.

[0079] In addition, as the light-emitting dopant material, a material emitting delayed fluorescence such as a CDCB derivative such as PIC-TRZ, CC2TA, PXZ-TRZ, 4CzIPN, and the like can be used.

[0080] Further, the mass ratio of the dopant to the light-emitting host is 1:99 to 50:50.

[0081] A consumer product made from the organic electroluminescent device, the consumer product comprising the organic electroluminescent device provided by the present application.

[0082] The consumer product described in the present application can be one of the following products: flat panel displays, computer monitors, medical monitors, televisions, billboards, lamps for interior or exterior illumination and / or signaling, head-up displays, fully transparent or partially transparent displays, flexible displays, laser printers, telephones, cellular phones, tablet computers, phablets, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, camcorders, 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, theater or stadium screens, phototherapy devices, and signs.

[0083] The raw materials used in the present application can be obtained from commercial suppliers unless otherwise specified. Any range recited in the present application includes the endpoints and any number between the endpoints and any range defined by any two endpoints.

[0084] Compared with the prior art, the present application has the following advantages:

[0085] The organic electroluminescent compound described in the present application has a novel rigid structure of large planar conjugated anthracene and boron atom, and the resonance effect of boron atom with O, S or Se heteroatom is utilized to improve the internal quantum efficiency. As for the organic electroluminescent compound represented by the general formula (I) of the present application, it has the following characteristics: (1) large carrier mobility; (2) high internal quantum efficiency; (3) stable thin film state; (4) excellent heat resistance, and thus is suitable for use as a material constituting the light-emitting layer of the organic electroluminescent element of the present application.

[0086] As for the organic electroluminescent element of the present application using the organic electroluminescent compound represented by the above general formula (I) of the present application as a host material of the light-emitting layer, since a compound having large carrier mobility, high internal quantum efficiency, excellent amorphousness, and stable thin film state is used, a high-efficiency, low-driving-voltage, long-life organic electroluminescent element can be realized.

[0087] Furthermore, in the present application, by forming the light-emitting layer with the organic electroluminescent compound of the above general formula (I), the high quantum efficiency performance and heat resistance of the compound can be maximally utilized, and a long-life organic electroluminescent element can be realized with higher efficiency.

[0088] In addition, in the present application, the organic electroluminescent device of the present application using the organic electroluminescent compound represented by General Formula (I) as a material thereof in at least any one of the light-emitting layer or the stacked film of two or more light-emitting layers described above can achieve an organic electroluminescent device with high efficiency, low driving voltage, and long lifetime because a compound with high carrier mobility, high internal quantum efficiency, and excellent amorphous property, and stable in a thin film state is used. BRIEF DESCRIPTION OF DRAWINGS

[0089] In order to more clearly illustrate the technical solutions of the embodiments of the present application or the prior art, the following will briefly introduce the drawings needed to be used in the embodiments or prior art description. Obviously, the drawings in the following description are only some embodiments of the present application, and for those skilled in the art, other drawings can also be obtained from these drawings without creative labor.

[0090] Figure 1 An organic light-emitting device 100 is shown schematically. The drawing is not necessarily drawn to scale. The device 100 can 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 can be fabricated by sequentially depositing the described layers.

[0091] Figure 2 An organic light-emitting device 200 is shown schematically that exhibits 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. The device 200 can be prepared by sequentially depositing the described layers. Because the most common OLED device has one light-emitting layer, and the device 200 has a first light-emitting layer and a second light-emitting layer, the light-emitting peaks of the first light-emitting layer and the second light-emitting layer can be overlapping or cross-overlapping or non-overlapping. In the corresponding layers of the device 200, similar materials to those described with respect to the device 100 can be used. Figure 2 One example of how some layers can be added from the structure of the device 100 is provided. DETAILED DESCRIPTION

[0092] In order to make the objectives, technical solutions and advantages of the present application clearer, the technical solutions of the present application will be described in detail below. Obviously, the described embodiments are only some of the embodiments of the present application, but not all the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those of ordinary skill in the art without creative work fall within the scope of the present application.

[0093] In the present application, the preparation methods are all conventional methods unless otherwise specified. The raw materials used are all available from public commercial channels unless otherwise specified, and the percentages are all mass percentages unless otherwise specified. The present application provides a series of novel organic compounds, and all the reactions are carried out under well-known suitable conditions. Some of them involve simple organic preparation, for example, the preparation of phenylboronic acid derivatives, which can be synthesized by skilled operation skills, and are not described in detail in the present application.

[0094] The test instruments and methods for testing the performance of OLED materials and elements in the following examples are as follows:

[0095] OLED element performance detection conditions:

[0096] Luminance and chromaticity coordinates: tested using a spectral scanner PhotoResearch PR-715;

[0097] Current density and turn-on voltage: tested using a digital source meter Keithley 2420;

[0098] Power efficiency: tested using a NEWPORT 1931-C;

[0099] Lifetime test: tested using a LTS-1004AC lifetime test device.

[0100] The present application does not provide a preparation method of the compound represented by formula (I). When X exists, the synthesis of the compound represented by formula (I) can be prepared according to scheme 1 or scheme 2,

[0101] Scheme 1:

[0102]

[0103] Scheme 2:

[0104]

[0105] When X does not exist, the synthesis of the compound represented by formula (I) can be prepared according to scheme 3,

[0106] Scheme 3:

[0107]

[0108] In Schemes 1 to 3, Y each independently represents F, CI, Br, I or OTf; the meanings of the remaining symbols are defined as above.

[0109] The starting materials for the synthesis of the compounds of formula (I) can be purchased commercially. The principles of the methods, the procedures, the usual work-up, the purification by column chromatography, the purification by recrystallization are well known to the synthesis chemist and the synthesis process can be carried out without any further instruction.

[0110] In particular, in Scheme 1, the compound of formula (I) is prepared from the o- aldehylbisbenzyl halide S0 containing R 3 and R 4 is subjected to a SUZUKI coupling reaction with a boronic acid or pinacol boronic ester of diaryl X ether Int.-1 to give the aldehyde containing intermediate S1, which is subjected to a ring closure under catalysis of boron trifluoride etherate to give the anthracene compound S2, which is subjected to a halogenation reaction to give the dihalogenated anthracene intermediate S3, which is subjected to a SUZUKI coupling reaction with a boronic acid or pinacol boronic ester of Ar 1 to give the 10-Ar 1 halogenated anthracene derivative S4, which is then subjected to a lithiation with butyllithium and a substitution reaction with boron tribromide or boron triiodide to give the compound of formula (I) of the present application. The boronic acid or pinacol boronic ester of the intermediate Ar 1 and the boronic acid or pinacol boronic ester of diaryl X ether Int.-1 are prepared by a palladium catalyzed or base catalyzed coupling reaction.

[0111] In Scheme 2, the compound of formula (I) with the dotted line as a connecting bond is prepared from the halogen atom containing A0 (prepared by referring to the synthetic method of Scheme 1) which is subjected to a SUZUKI coupling reaction with a boronic acid or pinacol boronic ester of m-halide to give the aldehyde containing intermediate A1, which is subjected to a ring closure under catalysis of boron trifluoride etherate to give the anthracene compound A2, which is subjected to a substitution reaction with a base to give the cyclized intermediate A3, which is subjected to a halogenation reaction to give the dihalogenated anthracene intermediate A4, which is subjected to a SUZUKI coupling reaction with a boronic acid or pinacol boronic ester of Ar 1 to give the monohalogenated anthracene derivative A5, which is then subjected to a lithiation with butyllithium and a substitution reaction with boron tribromide or boron triiodide to give the compound of formula (I) of the present application. The boronic acid or pinacol boronic ester of the intermediate Int.-2 and Ar 1 are prepared by a palladium catalyzed or base catalyzed coupling reaction.

[0112] In Scheme 3, the compound of formula (I) without X is prepared by a SUZUKI coupling reaction of a halogen atom-containing B0(prepared by referring to the synthetic method of Scheme 1) with a boronic acid or boronic acid pinacol ester of ring B to prepare an aldehyde group-containing intermediate B1, the aldehyde group-containing intermediate B1 is catalytically closed ring by boron trifluoride ether to prepare an anthracene compound B2, the anthracene compound B2 is subjected to a halogenation reaction to prepare a dihalogenated anthracene intermediate B3, the dihalogenated anthracene intermediate B3 is subjected to a SUZUKI coupling reaction with a boronic acid or boronic acid pinacol ester of Ar 1 to prepare a monohalogenated anthracene derivative B4, and then the B4 is subjected to a lithiation with butyllithium and a substitution reaction with boron tribromide or boron triiodide to prepare the compound of formula (I) of the present application. The intermediate Int.-3 and Ar 1 are prepared by a palladium-catalyzed or base-catalyzed coupling reaction.

[0113] As the palladium catalyst that can be used in the palladium-catalyzed coupling reaction, any one of Pd(P-tBu3)2, Pd(PPh3)4, Pd2(dba)3, Pd2(dba)3CHCl3, PdCl2(PPh3)2, PdCl2(CH3CN)2, Pd(OAc)2, Pd(acac)2, Pd / C, PdCl2, [Pd(allyl)Cl]2, and the like, or a mixture of two or more thereof can be selected.

[0114] Further, the base used in the palladium-catalyzed coupling reaction or the base-catalyzed coupling reaction can be selected from sodium tert-butoxide, potassium tert-butoxide, sodium hydride, lithium hydride, sodium tert-amylate, sodium ethoxide, sodium methoxide, sodium carbonate, potassium carbonate, cesium carbonate, lithium, potassium hydride, triethylamine, cesium fluoride, and the like, and a mixture of one or two or more thereof.

[0115] The coupling reaction can be carried out in an organic solvent, and the organic solvent can be selected from ether solvents such as diethyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, ethylene glycol diethyl ether, ethylene glycol diethylether, ethylene glycol methyl ether, diethylene glycol diethyl ether, and anisole, aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, dichlorobenzene, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, sulfolane, and the like, and a mixture of one or two or more thereof can be used.

[0116] In order to more specifically illustrate the present application, the following will cite the preparation methods of some specific compounds, but not limited to the compounds presented below.

[0117] Example 1

[0118] The preparation method of the compound CJHB977 includes the following steps:

[0119] First step: preparation of the compound Int-1

[0120]

[0121] Under nitrogen protection, 90.0 mmol of di(2-bromophenyl)methane, 100.0 mmol of m-phenoxyphenylboronic acid and 300 mL of toluene were mixed, 117.0 mmol of anhydrous sodium carbonate and 1.0 g of Pd(PPh3)4 catalyst were added, and then 100 mL of ethanol and 50 mL of water were added. The temperature was raised to reflux and stirred for 10 hours. After cooling to room temperature, 100 mL of water was added, the organic phase was separated, the aqueous phase was extracted with toluene, the organic phase was concentrated under reduced pressure, and purified by silica gel column separation to obtain Int-1 as a white solid with a yield of 75%.

[0122] Step 2: Preparation of compound Int-2

[0123]

[0124] Take 55.0 mmol of the intermediate Int-1 prepared in the first step and dissolve it in 300 mL of dry THF. Under nitrogen protection, cool it to -78°C, add 66.0 mmol of 2.5 M n-butyl lithium n-hexane solution dropwise, stir and react for 30 minutes, then add 82.5 mmol of DMF dropwise, warm to room temperature, add 100 mL of 3 M dilute hydrochloric acid, extract with ethyl acetate, collect the organic phase, dry and filter, concentrate the filtrate under reduced pressure, and separate and purify it on a silica gel column to obtain Int-2 as a yellow solid with a yield of 82%.

[0125] Step 3: Preparation of compound Int-3

[0126]

[0127] Take 50.0 mmol of the intermediate Int-2 prepared in the second step and dissolve it in 250 mL of dry dichloromethane. Under nitrogen protection, add 20.0 mmol of boron trifluoride ether solution dropwise. Stir and react for 10 minutes. Concentrate under reduced pressure and purify it by silica gel column to obtain Int-3 as a yellow solid in a yield of 89%.

[0128] Step 4: Preparation of compound Int-4

[0129]

[0130] Under nitrogen protection, 40.0 mmol of intermediate Int-3 was dissolved in 120 mL of dichloromethane, and the ice-salt bath was cooled to -10 °C. 4.0 mmol of p-toluenesulfonic acid was added, and 84.0 mmol of N-bromosuccinimide was added portionwise. The reaction was stirred for 2 hours. 50 mL of saturated aqueous sodium thiosulfate solution was added, and dichloromethane was used for extraction. The organic phase was collected and dried for filtration. The filtrate was concentrated under reduced pressure to dryness, and recrystallized with toluene / THF to obtain Int-4, a yellow solid, with a yield of 90%.

[0131] Fifth step: preparation of compound Int-5

[0132]

[0133] Under nitrogen protection, 20.0 mmol of Int-4, 22.0 mmol of (9-phenyldibenzo[b,d]furan-2-yl)boronic acid pinacol ester, and 80 mL of toluene were mixed. 40.0 mmol of anhydrous sodium carbonate and 5.0 mg of Pd132 catalyst were added, followed by 40 mL of ethanol and 40 mL of water. The reaction was stirred at reflux for 10 hours. After cooling to room temperature, 50 mL of water was added, and the organic phase was separated. The aqueous phase was extracted with ethyl acetate, and the organic phase was concentrated under reduced pressure to dryness. Recrystallization with toluene / THF yielded compound Int-5, a yellow solid, with a yield of 72%.

[0134] Sixth step: preparation of compound CJHB977

[0135]

[0136] Under nitrogen protection, 20.0 mmol of intermediate Int-5 prepared in the fifth step was dissolved in 120 mL of dry tert-butylbenzene, and the temperature was lowered to -100 °C. 24.0 mmol of 2.5 M n-butyllithium n-hexane solution was added dropwise, and the reaction was stirred for 10 minutes. Then, 30.0 mmol of boron triiodide was added dropwise, and the temperature was raised to room temperature. The reaction was stirred for 1 hour, 0.1 mol of triethylamine was added, the temperature was raised to 150 °C, and the reaction was stirred for 5 hours. After cooling to room temperature, the reaction was concentrated under reduced pressure to dryness. Purification was performed by silica gel column separation to obtain compound CJHB977, a yellow solid, with a yield of 36% and MS (TOF): m / z 597.1962 [M+H] + .

[0137] Example 2

[0138] Preparation of compound CJHB1052, comprising the following steps:

[0139] First step: preparation of compound Int-6

[0140]

[0141] To 15.0 mmol of 3-bromo-2-(bromobenzyl)benzonitrile-d6 was added 60 mL of toluene under nitrogen protection, 36.0 mmol of phenanthryl-9-boronic acid, 54.0 mmol of anhydrous sodium carbonate and 173.0 mg of Pd(PPh3)4 catalyst, and then 30 mL of ethanol and 30 mL of water were added. The reaction was stirred at reflux for 15 hours, cooled to room temperature, filtered, and the filter cake was washed with water and ethanol and purified by silica gel column separation to obtain compound Int-6 in the form of a yellow solid with a yield of 78%.

[0142] Second step: Preparation of compound Int-7

[0143]

[0144] Under nitrogen protection, 20.0 mmol of Int-6 was dissolved in 80 mL of dry THF, and the temperature was lowered to -78°C. Then, 24.0 mmol of diisobutylaluminum hydride was added dropwise, and the reaction was stirred for 1 hour. Then, 50 mL of 2M dilute hydrochloric acid aqueous solution was added dropwise, and the temperature was raised to room temperature. The organic phase was separated, the aqueous phase was extracted with ethyl acetate, dried, filtered, and the filtrate was concentrated under reduced pressure and purified by silica gel column separation to obtain compound Int-7 in the form of a yellow solid with a yield of 94%.

[0145] Third step: Preparation of compound Int-8

[0146]

[0147] Compound Int-8 was prepared in the form of a yellow solid with a yield of 91% according to the synthesis method of the third step of Example 1, except that Int-2 in the third step of Example 1 was replaced by Int-7.

[0148] Fourth step: Preparation of compound Int-9

[0149]

[0150] Compound Int-9 was prepared in the form of a yellow solid with a yield of 93% according to the synthesis method of the fourth step of Example 1, except that Int-3 in the fourth step of Example 1 was replaced by Int-8.

[0151] Fifth step: Preparation of compound Int-10

[0152]

[0153] Compound Int-10 was prepared in the form of a yellow solid with a yield of 78% according to the synthesis method of the fifth step of Example 1, except that Int-4 in the fifth step of Example 1 was replaced by Int-9 and (9-phenyldibenzo[b,d]furan-2-yl)boronic acid pinacol ester was replaced by phenylboronic acid-d5.

[0154] Step 6: Preparation of compound CJHB1052

[0155]

[0156] Compound CJHB1052 was prepared according to the synthetic procedure described in Step 6 of Example 1, by replacing Int-5 in Step 6 of Example 1 with Int-10, in yield of 55% as a yellow solid, MS (TOF): m / z 626.2908 [M+H] + .

[0157] The following compounds were prepared according to the synthetic procedures described in Example 1 and Example 2 above:

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169] Example 3

[0170] An OLED device, as shown in Figure 1 was prepared by the following steps:

[0171] 1) The ITO coated glass substrate was treated in a cleaning solution for 30 minutes, rinsed in deionized water, sonicated in a mixture of acetone / ethanol for 30 minutes, baked to dryness in a clean environment, irradiated in a UV light cleaner for 10 minutes, and bombarded with a low energy cation beam.

[0172] 2) The treated ITO glass substrate was placed in a vacuum chamber and pumped down to less than 1 x 10 -5Pa, and silver was evaporated as an anode on the above ITO film to a film thickness of 2000 A. Compound DNTPD and F4TCNQ were further evaporated as a hole injection layer, F4TCNQ being 3% by mass of DNTPD, to a film thickness of 1000 A. NPD was further evaporated as a hole transport layer on the above hole injection layer film to a film thickness of 2000 A.

[0173] 3) Compound HT202 was further evaporated as an electron blocking layer on the hole transport layer to a film thickness of 1000 A.

[0174] 4) A compound represented by Formula I of the present application and BD021 were further evaporated as an organic light emitting layer on the electron blocking layer, wherein BD021 is a dopant material and the compound represented by Formula I of the present application is a host material, the doping concentration of the compound represented by Formula I in BD021 being 8%, to a film thickness of 2000 A.

[0175] 5) Compound LiQ and ET215 were further evaporated as an electron transport layer on the above light emitting layer, wherein the mass ratio of LiQ and ET215 was 1:1, to a film thickness of 2000 A.

[0176] 6) Compound LiF was further evaporated as an electron injection layer on the above electron transport layer to a film thickness of 2000 A. Finally, magnesium and silver were evaporated as a cathode layer on the above electron injection layer, the mass ratio of magnesium and silver being 1:10, to a film thickness of 2000 A.

[0177] The structure of the compound used in the above Example 3 is as follows:

[0178]

[0179] Comparative Example 1

[0180] The same procedure as in Reference Example 3 was followed, except that compound B01 was used instead of the compound represented by Formula I. The structure of compound B01 is as follows:

[0181]

[0182] The driving voltage and current efficiency of the organic electroluminescent element prepared in Example 3 and Comparative Example 1 were measured using a digital source meter and a luminance meter at the same luminance, and the lifetime of the element was also measured. Specifically, the voltage was increased at a rate of 0.1 V per second, and the driving voltage at which the luminance of the organic electroluminescent element reached 1000 cd / m2was measured. The current efficiency at the same luminance was also measured. The lifetime of the element was measured by measuring the time until the luminance of the element reached 80% of the initial luminance. 2The voltage at this time is the driving voltage, and the current density at this time is measured simultaneously; the ratio of the brightness to the current density is the current efficiency; the LT90% lifetime test is as follows: using a luminance meter, the luminance of the organic electroluminescent element is measured at 1000 cd / m 2 The brightness at this time is 900 cd / m 2 The time is in hours. All results are summarized in Table 1, and all results are reported as relative values normalized to the results of Comparative Example 1.

[0183] Table 1: Performance test results of each element

[0184]

[0185]

[0186]

[0187] As can be seen from Table 1, the compound of the present application as a light-emitting material obtains a blue light organic electroluminescent element, the driving voltage of the element is reduced, the current efficiency is improved, and the LT90% lifetime is also improved.

[0188] The organic electroluminescent device of the present application can be applied in wall-mounted televisions, flat panel displays, planar light emitters for lighting, copiers, printers, backlights for liquid crystal displays, or light sources for measuring instruments, display panels, identification lights, and the like.

[0189] The above description is merely a specific implementation of the present application, but the protection scope of the present application is not limited thereto. Any person skilled in the art can easily think of changes or replacements within the technical scope disclosed by the present application, which should be covered within the protection scope of the present application. Therefore, the protection scope of the present application should be subject to the protection scope of the claims.

Claims

1. An organic electroluminescent compound, characterized by The organic electroluminescent compound is selected from the group consisting of the following structures: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 ； wherein each T is independently selected from O, S, or NR 5 ; X is selected from O or no X; R 1 , R 2 , R 3 , R 4 are each identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, cyano; R 5 is phenyl; said Ar 1 is selected from the group consisting of phenyl, biphenyl, terphenyl, quaterphenyl, phenanthryl, triphenylenyl, anthryl, benzanthryl, pyrenyl, chrysenyl, perylenyl, fluoranthenyl, carbazolyl, fluorenyl, indolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, or dibenzothiophene.

2. An organic electroluminescent compound, characterized by The compound is selected from one of the following CJHB950~CJHB1090 structures: The hydrogen atoms in the above structures can be partially or entirely replaced by deuterium.

3. An organic electroluminescent material, characterized in that: The organic electroluminescent material comprises the organic electroluminescent compound of claim 1 or 2.

4. An organic electroluminescent device, characterized by comprising 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 organic electroluminescent compound of claim 1 or 2.

5. The organic electroluminescence device according to claim 4, wherein The organic electroluminescent compound is contained in a light-emitting layer.

6. A consumer product, characterized in that The organic electroluminescent device of claim 4 is contained.

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