CN113248477A - Organic compound, organic electroluminescent material and organic electroluminescent element - Google Patents

Organic compound, organic electroluminescent material and organic electroluminescent element Download PDF

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CN113248477A
CN113248477A CN202110527450.6A CN202110527450A CN113248477A CN 113248477 A CN113248477 A CN 113248477A CN 202110527450 A CN202110527450 A CN 202110527450A CN 113248477 A CN113248477 A CN 113248477A
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organic electroluminescent
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曹建华
董智超
唐怡杰
侯斌
洪丽
陈剑锋
冀鹏飞
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Beijing Bayi Space LCD Technology Co Ltd
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Abstract

The invention relates to an organic compound, an organic electroluminescent material and an organic electroluminescent element, wherein the structural formula of the compound is shown as the formula (I): when the organic compound is used for preparing an organic electroluminescent elementThe organic compound has better film-forming property, and when the organic compound is applied to an electron transport layer and an electron transport auxiliary layer, the organic compound can manufacture an organic electroluminescent element with lower driving voltage, higher luminous efficiency and longer service life compared with the prior electron transport material, and further can manufacture a full-color display panel with improved performance and service life.
Figure DDA0003066560310000011

Description

Organic compound, organic electroluminescent material and organic electroluminescent element
Technical Field
The invention belongs to the technical field of organic electroluminescent materials, and particularly relates to an organic compound, an organic electroluminescent material and an organic electroluminescent element.
Background
In general, the organic light emitting phenomenon refers to a phenomenon in which light is emitted when electric energy is applied to an organic substance. That is, when an organic layer is disposed between an anode and a cathode, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons transition to a ground state, light and heat are emitted.
As one method for efficiently manufacturing an organic electroluminescent element, studies have been made to replace an organic layer in a single-layer manufactured element with a multilayer structure, and in 1987, down proposed an organic electroluminescent element having a laminated structure of a hole layer and a functional layer of a light-emitting layer, and most of the organic electroluminescent elements currently used include: the light emitting device includes a substrate, an anode, a hole injection layer receiving holes from the anode, a hole transport layer transporting holes, a light emitting layer emitting light by recombination of holes and electrons, an electron transport layer transporting electrons, an electron injection layer receiving electrons from the cathode, and a cathode. The reason why the organic electroluminescent element is formed in a multilayer structure is that since the moving speeds of holes and electrons are different, if the hole injection layer and the transport layer, and the electron transport layer and the electron injection layer are appropriately formed, holes and electrons can be efficiently transported, and the balance between holes and electrons can be achieved in the element, thereby improving the exciton utilization rate.
In addition, many organic monomolecular substances having an imidazole group, an oxazole group, a thiazole group, and a spirofluorene group have been reported as substances that can be applied to an electron injection layer and a transport layer in the past. For example, TPBI described in chinese patents CN103833507B, CN107573328B, and CN107556310B and U.S. Pat. No. 5,645,948 issued by kodak in 1996 is a substance for an electron transport layer having an imidazole group, and has a structure in which three N-phenylbenzimidazole groups are contained in 1,3, and 5 substitution positions of benzene, and has a function of blocking holes crossing from a light-emitting layer in addition to an electron transport function, but has a problem of low thermal stability when actually applied to a device.
The present invention has been made in view of the above circumstances.
Disclosure of Invention
In order to solve the above problems in the prior art, the present invention provides an organic compound, an organic electroluminescent material and an organic electroluminescent device, wherein the organic compound of the present invention as a luminescent material can improve the stability and the light extraction efficiency of the luminescent device, and has the advantages of long service life and the like.
In a first aspect of the present invention, there is provided an organic compound, wherein the structural formula of the compound is shown in formula (I):
Figure BDA0003066560290000021
wherein G is selected from O, S, NAr1Or CR13R14；
R1～R14Each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40Alkyl of (C)2-C40Alkenyl of, C2-C40Alkynyl of (A), C3-C40Cycloalkyl of (2), heterocycloalkyl of atomic number 3 to 40, C6-C60Aryl of (C)2-C60Heteroaryl of (A), C1-C40Alkoxy group of (C)6-C60Aryloxy group of (A), C1-C40Alkylsilyl group of (C)6-C60Arylsilyl group of (C)1-C40Alkyl boron group of (2), C6-C60Aryl boron group of (1), C6-C60Aryl phosphorus radical of (2), C6-C60Aryl phosphorus oxide group of (1), C6-C60Any two or more adjacent substituents may be optionally joined or fused, or bridged to each other by a bridging group bonded to the same nitrogen atom, phosphorus atom, boron atom, oxygen, or sulfur, forming a single ring or a fused ring;
Ar1selected from the group consisting of C6-C60Aryl of (C)2-C60Heteroaryl of (A), C6-C60Aryl boron group of (1), C6-C60Aryl phosphorus radical of (2), C6-C60Aryl phosphorus oxide group of (2) and C6-C60Arylamine groups of (a).
Further, said C2-C60The heteroaryl group of (a) is one of the following structures:
Figure BDA0003066560290000031
wherein Z is1、Z2Each independently selected from hydrogen, deuterium, a halogen atom, a hydroxyl group, a nitrile group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a carboxylate thereof, a sulfonic group or a sulfonate thereof, a phosphoric group or a phosphate thereof, C1-C40Alkyl radical, C2-C40Alkenyl radical, C2-C40Alkynyl, C1-C40Alkoxy radical, C3-C40Cycloalkyl radical, C3-C40Cycloalkenyl radical, C6-C60Aryl radical, C6-C60Aryloxy radical, C6-C60Aryl boron group of (1), C6-C60Aryl phosphorus radical of (2), C6-C60Aryl phosphorus oxide group of (1), C6-C60Arylamino or C of2-C60One of the heteroaryl groups of (a);
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;
T1represents oxygen, sulfur, CR15R16Or NAr2；
The R is15And R16Each independently selected from hydrogen, deuterium, C1-C40Alkyl of (C)2-C40Alkenyl of, C2-C40Alkynyl of (A), C3-C40Cycloalkyl of (2), heterocycloalkyl of atomic number 3 to 40, C6-C60Aryl of (C)2-C60Heteroaryl of (a);
ar is2Selected from the group consisting of C6-C60Aryl of (C)2-C60Heteroaryl of (A), C6-C60Aryl boron group of (1), C6-C60Aryl phosphorus radical of (2), C6-C60Aryl phosphorus oxide group of (2) and C6-C60Arylamine groups of (a).
Figure BDA0003066560290000041
Represents a bond between a substituent and the main structure.
Further, G is selected from O, S or CR13R14；
Further, said R1～R14Each independently selected from hydrogen, deuterium, C1-C40Alkyl of (C)6-C60Aryl of (C)2-C60Heteroaryl of (A), C6-C60Aryl phosphorus radical of (2), C6-C60Aryl phosphorus oxide group of (1), C6-C60Arylamine groups of (a).
Further, the heteroaryl group is selected from the group consisting of pyrimidine, pyrazine, triazine, imidazole, benzimidazole, phenanthroimidazole, imidazopyridine, triazolopyridine and quinazoline;
the pyrimidine, pyrazine, triazine, imidazole, benzimidazole, phenanthroimidazole, imidazopyridine, triazolopyridine and quinazoline may each be independently deuterium, halogen, cyano, nitro, C1-C40Alkyl of (C)2-C40Alkenyl of, C2-C40Alkynyl of (A), C3-C40Cycloalkyl of, C3-C40Heterocycloalkyl of (A), C6-C60Aryl of (C)2-C60Heteroaryl of (A), C1-C40Alkoxy group of (C)6-C60Aryloxy group of (A), C1-C40Alkylsilyl group of (C)6-C60Arylsilyl group of (C)1-C40Alkyl boron group of (2), C6-C60Aryl boron group of (1), C6-C60Aryl phosphorus radical of (2), C6-C60Aryl phosphorus oxide group of (2) and C6-C60When the substituent is plural, plural substituents may be the same as or different from each other.
The organic compound according to the present invention can have higher thermal stability than conventional light-emitting materials by introducing various substituents, particularly aryl and/or heteroaryl groups, so that the molecular weight of the compound is significantly increased and the glass transition temperature is increased. Therefore, the performance and life characteristics of the organic electroluminescent element including the compound according to the present invention can be greatly improved. The organic electroluminescent element with such improved performance and life characteristics can eventually maximize the performance of a full-color organic light-emitting panel.
Further, the organic compound is one of CJHP 01-CJHP 148, and the specific structural formula is as follows:
Figure BDA0003066560290000051
Figure BDA0003066560290000061
Figure BDA0003066560290000071
Figure BDA0003066560290000081
Figure BDA0003066560290000091
Figure BDA0003066560290000101
wherein, T2is-O-, -S-, or one of the following structures:
Figure BDA0003066560290000102
T3is-O-, -S-, or one of the following structures:
Figure BDA0003066560290000103
and represents a bond.
Alkyl in the sense of the present invention means a monovalent functional group obtained by removing a hydrogen atom from a straight-chain or branched saturated hydrocarbon having 1 to 40 carbon atoms, and includes, as non-limiting examples thereof, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl and the like.
An alkyloxy group, preferably having 1 to 40 carbon atoms, in the sense of the present invention is taken to mean methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexoxy, n-heptoxy, cycloheptoxy, n-octoxy, cyclooctoxy, 2-ethylhexoxy, pentafluoroethoxy, 2, 2-trifluoroethoxy and the like.
Heteroalkyl in the sense of the present invention is preferably one having 1 to 40 carbon atoms, such as, as non-limiting examples, alkoxy, alkylthio, fluorinated alkoxy, fluorinated alkylthio, in particular methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutoxy, sec-butylthio, tert-butylthio, trifluoromethylthio, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2,2, 2-trifluoroethoxy, 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.
In general, the cycloalkyl, cycloalkenyl groups of the present invention are preferably those having a number of carbon atoms of 3 to 40, such as, as non-limiting examples thereof, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, cyclooctenyl, wherein one or more-CH2The radicals may be replaced by the radicals mentioned above; furthermore, one or more hydrogen atoms may also be replaced by deuterium atoms, halogen atoms, or nitrile groups.
The heterocycloalkyl group according to the present invention means a monovalent functional group obtained by removing a hydrogen atom from a non-aromatic hydrocarbon having 3 to 40 carbon atoms. At this time, one or more carbons, preferably 1 to 3 carbons, in the ring are substituted with a hetero atom such as nitrogen, oxygen, or sulfur, and as non-limiting examples thereof, morpholine, pyran, piperazine, and the like.
The alkenyl group according to the present invention may be a monovalent functional group obtained by removing a hydrogen atom from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon double bonds. As non-limiting examples thereof, there are vinyl, allyl, isopropenyl, 2-butenyl, heptenyl, octenyl and the like.
The alkynyl group according to the present invention means a monovalent functional group obtained by removing a 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, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl and the like.
The aryl group according to the present invention means a monovalent functional group obtained by removing a hydrogen atom from a single ring or an aromatic hydrocarbon having 6 to 60 carbon atoms in combination of two or more. In this case, two or more rings may be attached to each other or in a condensed form. As non-limiting examples thereof, there may be mentioned phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, pyrenyl,
Figure BDA0003066560290000121
A phenyl group, a perylene group, a fluoranthenyl group, a tetracenyl group, a pentacenyl group, a benzopyrenyl group, a biphenyl group, an idophenyl group, a terphenyl group, a fluorenyl group, a spirobifluorenyl group, a phenanthrenyl group, a pyrenyl group, a tetrahydropyrenyl group, an indenyl group, a cis-or trans-indenofluorenyl group, a cis-or trans-indenocarbazolyl group, a cis-or trans-indonocarbazolyl group, a triindenyl group, an isotridecyl group, a spiroisotridecyl group, a furyl group, a benzofuryl group, an isobenzofuryl group, a dibenzofuryl group, a thienyl group, a benzothienyl group, an isobenzothienyl group, a dibenzothienyl group, a pyrrolyl group, an indolyl group, an isoindolyl group, a carbazolyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, an acridinyl group, a phenanthridinyl group, a benzo [5, 6.]Quinolyl, benzo [6,7 ]]Quinolyl, benzo [7,8 ]]Quinolyl, phenothiazinyl, phenoxazine, pyrazolesA group, an indazolyl group, an imidazolyl group, a benzimidazolyl group, a naphthoimidazolyl group, a phenanthroimidazolyl group, a pyridoimidazolyl group, a pyrazinoimidazolyl group, a quinoxaloimidazolyl group, an oxazolyl group, a benzoxazolyl group, a naphthooxazolyl group, an anthraoxazolyl group, a phenanthrooxazolyl group, an isoxazolyl group, a 1, 2-thiazolyl group, a 1, 3-thiazolyl group, a benzothiazolyl group, a pyridazinyl group, a hexaazatriphenylphenanthryl group, a benzopyrazinyl group, a pyrimidinyl group, a benzopyrimidinyl group, a quinoxalinyl group, a 1, 5-diazenanthrenyl group, a 2, 7-diazapynyl group, a 2, 3-diazapynyl group, a 1, 6-diazapynyl group, a 1, 8-diazapynyl group, a 4,5,9, 10-tetraazapyryl group, a pyrazinyl group, a phenoxazinyl group, phenothiazinyl group, a, fluoryl group, naphthyridinyl group, Azacarbazolyl, benzocarbazinyl, 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 and benzothiadiazolyl groups or groups derived from a combination of these systems.
The aryloxy group, the arylboron group, the arylphosphorus group and the arylphosphorus oxide group in the present invention mean a monovalent functional group in which an aryl group having 6 to 60 carbon atoms is bonded to an oxygen atom, a boron atom, a phosphorus oxide and a nitrogen atom. As non-limiting examples, there are phenoxy, naphthoxy, diphenoxy, dibenzene-boron, diphenylphosphino oxide, diphenylamine and the like.
The alkylsilyl group in the present invention means a silyl group substituted with an alkyl group having 1 to 40 carbon atoms, the arylsilyl group means a silyl group substituted with an aryl group having 6 to 60 carbon atoms, and the arylamine means an amine substituted with an aryl group having 6 to 60 carbon atoms.
In a second aspect of the present invention, there is provided an organic electroluminescent material comprising the organic compound.
A third object of the present invention is to provide an organic electroluminescent element comprising a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, the organic layers containing the organic compound.
The organic electroluminescent element includes 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-injecting layers, hole-transporting layers, hole-blocking layers, electron-transporting layers, electron-injecting layers, exciton-blocking layers, electron-blocking layers and/or charge-generating layers. Among them, the organic layer containing the compound represented by the above formula (I) is preferably a light-emitting layer, an electron transport layer, and an electron transport auxiliary layer further stacked on the electron transport layer. In this case, the compound represented by the above chemical formula (I) can be used as a host substance or an electron transport layer and an electron transport auxiliary layer substance of the above light-emitting layer. However, it should be noted that each of these layers need not be present. The organic electroluminescent element described herein may include one light-emitting layer, or it may include a plurality of light-emitting layers. That is, a plurality of light-emitting compounds capable of emitting light are used in the light-emitting layer. Particularly preferred are systems with three light-emitting layers, wherein the three layers can exhibit blue, green and red light emission. If more than one light-emitting layer is present, at least one of these layers comprises, according to the invention, a compound according to the invention.
The present invention provides an organic electroluminescent element comprising the compound represented by the above formula (I). Specifically, the organic electroluminescent element according to the present invention comprises a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, wherein at least one of the one or more organic layers comprises a compound represented by the formula (I). In this case, the above-mentioned compounds may be used alone or in combination of two or more. The one or more organic layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. Preferably, the organic layer including the compound of formula (I) may be a light emitting layer, an electron transport layer, and a hole transport layer, and more preferably, may be an electron transport layer or a hole transport layer.
The light-emitting layer of the organic electroluminescent element according to the present invention may contain a host material, and in this case, the compound of the above formula (I) may be contained as the host material. When such a light-emitting layer contains the compound represented by the above formula (I), the carrier transport ability increases, and the chance of combining holes and electrons in the light-emitting layer increases, so that an organic electroluminescent element excellent in efficiency, lifetime, luminance, and driving voltage can be provided. In addition, the light-emitting layer of the organic electroluminescent element of the present invention may contain a compound other than the compound represented by the above formula (I) as a dopant.
The electron transport layer of the organic electroluminescent element of the present invention may contain an electron transport material, and in this case, may contain a compound represented by the above formula (I). When the electron transport layer contains the compound represented by the formula (I), the electron transport ability is enhanced by the two electron-withdrawing groups, and the injected electrons can be smoothly transported to the light-emitting layer, so that an organic electroluminescent element having excellent efficiency, lifetime, luminance, driving voltage, and the like can be provided. Wherein an electron transport assisting layer may be further laminated on the electron transport layer. In the case where the compound represented by the above formula (I) is contained in the transport auxiliary layer, the efficiency, lifetime, driving voltage, and the like of the blue organic electroluminescent element can be improved particularly because the effect of preventing excitons from transitioning from the light-emitting layer and the electron transport layer is achieved due to the high triplet energy level.
The organic electroluminescent element of the present invention is not particularly limited in structure, and may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked as shown in fig. 1 and 2, as a non-limiting example. An electron injection layer may be further stacked on the electron transport layer, and a hole blocking layer may be further stacked on the light emitting layer. In addition, the organic electroluminescent element of the present invention may have a structure in which an insulating layer or an adhesive layer is interposed between an electrode and an organic layer.
In the description of the present invention, "a plurality" means two or more unless otherwise specified; the terms "upper", "lower", and the like, indicate orientations or positional relationships based on the orientations or positional relationships shown in the drawings, and are only for convenience in describing the present invention and simplifying the description, but do not indicate or imply that the referred devices or elements must have a specific orientation, be constructed and operated in a specific orientation, and thus, should not be construed as limiting the present invention.
Further, the organic layer is a light-emitting layer, an electron transport layer, an electron injection layer, an electron transport auxiliary layer, an electron blocking layer or a hole transport layer.
Further, the organic compound is a substance of an electron transport layer.
Further, the organic compound is a substance of a hole transport layer.
The organic electroluminescent element according to the invention does not comprise a separate hole-injecting layer and/or hole-transporting layer and/or hole-blocking layer and/or electron-transporting layer and/or electron-injecting layer, i.e. the light-emitting layer is directly adjacent to the hole-injecting layer or the anode and/or the light-emitting layer is directly adjacent to the electron-transporting layer or the electron-injecting layer or the cathode.
In the other layers of the organic electroluminescent device according to the invention, in particular in the hole-injecting layer and the hole-transporting layer and in the electron-injecting and electron-transporting layer, all materials can be used in the manner conventionally used according to the prior art. The person skilled in the art will thus be able to use all materials known for organic electroluminescent elements in combination with the light-emitting layer according to the invention without inventive effort.
Preference is furthermore given to organic electroluminescent arrangements which are characterized in that one or more layers are applied by means of a sublimation process, with a temperature of less than 10 ℃ in a vacuum sublimation apparatus-5Pa, preferably less than 10-6Pa is applied by vapor deposition. However, the initial pressure may also be even lower, e.g. below 10-7Pa。
Preference is likewise given to organic electroluminescent elements in which one or more layers are applied by means of an organic vapor deposition method or by means of carrier gas sublimation, which layers comprise a metal oxideIn 10-5The material is applied under a pressure between Pa and 1 Pa. A particular example of this method is the organic vapour jet printing method, in which the material is applied directly through a nozzle and is therefore structured.
Preference is furthermore given to organic electroluminescent elements in which one or more layers are produced from solution, for example by spin coating, or by means of any desired printing method, for example screen printing, flexographic printing, offset printing, photoinitiated thermal imaging, thermal transfer, ink-jet printing or nozzle printing. Soluble compounds, for example, are obtained by appropriate substitution of a compound of formula (I). These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, hybrid methods are possible, in which, for example, one or more layers are applied from solution and one or more further layers are applied by vapor deposition.
These methods are generally known to those skilled in the art, and they can be applied to an organic electroluminescent element comprising the compound according to the present invention without inventive labor.
The invention therefore also relates to a method for producing an organic electroluminescent element according to the invention, at least one layer being applied by means of a sublimation method, and/or at least one layer being applied by means of an organic vapour deposition method or by means of carrier gas sublimation, and/or at least one layer being applied from solution by spin coating or by means of a printing method.
Furthermore, the present invention relates to pharmaceutical compositions comprising at least one compound of the invention as indicated above. The same preferences as indicated above for the organic electroluminescent elements apply to the compounds according to the invention. In particular, the compounds may furthermore preferably comprise further compounds. The processing of the compounds according to the invention from the liquid phase, for example by spin coating or by printing methods, requires the preparation of the compounds according to the invention. These formulations may be, for example, solutions, dispersions or emulsions. For this purpose, it may be preferred 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, (-) -fenchytone, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3, 4-dimethylanisole, 3, 5-dimethylanisole, acetophenone, 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 butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1, 1-bis (3, 4-dimethylphenyl) ethane, or a mixture of these solvents.
In addition, unless otherwise specified, all starting materials for use in the present invention are commercially available, and any range recited herein includes any value between the endpoints and any subrange between the endpoints and any value between the endpoints or any subrange between the endpoints.
Compared with the prior art, the invention has the beneficial effects that:
when the organic compound is used for preparing an organic electroluminescent element, the organic compound has excellent electron mobility, thermal stability and luminescent property, and can be applied to an organic layer of the organic electroluminescent element.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the drawings without creative efforts.
FIG. 1 is a schematic view of a bottom emission example of an organic electroluminescent device of the present invention;
fig. 2 is a schematic view of one example of top emission of the organic electroluminescent device of the present invention.
Reference numerals
1-substrate, 2-anode, 3-hole injection layer, 4-hole transport layer/electron blocking layer, 5-luminescent layer, 6-hole blocking layer/electron transport layer, 7-electron injection layer and 8-cathode.
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 is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the examples given herein without any inventive step, are within the scope of the present invention.
The following examples were used to test the performance of OLED materials and devices using the following instruments and methods:
OLED device performance detection conditions:
luminance and chromaticity coordinates: testing with a photosresearch PR-715 spectrum scanner;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: tested using NEWPORT 1931-C.
Example 1
Compound CJHP19 (T)2O) comprising the steps of:
the first step is as follows: preparation of intermediate Int-1
Figure BDA0003066560290000181
24.0mmol of dibenzofuran-1-boronic acid (CAS:162607-19-4), 20.0mmol of 1-fluoro-2-iodonaphthalene (CAS:501433-09-6), 80.0mmol of sodium carbonate and 0.1mmol of Pd (PPh)3)4Adding 60mL of toluene, 30mL of ethanol and 30mL of water into the catalyst, heating, refluxing, stirring and reacting for 12 hours, cooling to room temperature, extracting with ethyl acetate, drying the organic phase, filtering, concentrating the filtrate under reduced pressure to dryness, separating and purifying by using a silica gel column, and recrystallizing by using ethanol to obtain an intermediate Int-1 with the yield of 82.4%.
The second step is that: preparation of intermediate Int-2
Figure BDA0003066560290000182
Dissolving 25.0mmol of intermediate Int-1 in 80mL of chlorobenzene, adding 37.5mmol of anhydrous aluminum chloride, heating to 80 ℃, stirring and reacting for 6 hours, cooling to room temperature, adding 50mL of 2N diluted hydrochloric acid aqueous solution, separating out an organic phase, washing with water, washing with sodium bicarbonate aqueous solution, washing twice, drying the organic phase, filtering, concentrating under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain an intermediate Int-2, wherein the yield is as follows: 94 percent.
The third step: preparation of intermediate Int-3
Figure BDA0003066560290000191
22.5mmol of intermediate Int-2 is dissolved in 100mL of dichloromethane, 22.5mmol of NBS and 0.7mmol of anhydrous ferric chloride are added, the mixture is stirred for reaction for 12 hours, 100mL of water is added, the mixture is stirred for 30 minutes, an organic phase is separated, washed by water, dried and filtered, the filtrate is decompressed and concentrated to dryness, and is separated and purified by a silica gel column, so that intermediate Int-3 is obtained, and the yield is 87%.
The fourth step: preparation of intermediate Int-4
Figure BDA0003066560290000192
12.0mmol of 9-phenanthreneboronic acid (CAS:68572-87-2), 10.0mmol of intermediate Int-3, 30.0mmol of sodium carbonate and 0.1mmol of Pd (PPh)3)4Adding 40mL of toluene, 20mL of ethanol and 20mL of water into the catalyst, heating, refluxing, stirring and reacting for 10 hours, cooling to room temperature, extracting with toluene, drying an organic phase, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain an intermediate Int-4 with the yield of 86%.
The fifth step: preparation of intermediate Int-5
Figure BDA0003066560290000193
Referring to the synthesis method of the third step, intermediate Int-5 was prepared in 94% yield by replacing Int-4 with Int-2 only in the third step.
And a sixth step: preparation of intermediate Int-6
Figure BDA0003066560290000201
Dissolving 20.0mmol of intermediate Int-5 in 80mL of dry THF, cooling to-90 ℃ under the protection of nitrogen, dropwise adding 10.0mL of 2.5M N-butyllithium N-hexane solution, stirring for reacting for 1 hour, dropwise adding 30.0mmol of triisopropyl borate, stirring for reacting for 1 hour, heating to 0 ℃, dropwise adding 80mL of 2N dilute hydrochloric acid aqueous solution, stirring for 30 minutes, separating an organic phase, extracting an aqueous phase with ethyl acetate, drying the organic phase, filtering, concentrating the filtrate under reduced pressure, adding N-hexane for dispersing, and filtering to obtain intermediate Int-6, wherein the yield is 76%.
The seventh step: compound CJHP19 (T)2O) preparation
Figure BDA0003066560290000202
12.0mmol of Int-6, 10.0mmol of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (CAS:3842-55-5), 30.0mmol of potassium phosphate hydrate and 5mg of Pd132 catalyst, 40mL of toluene, 20mL of ethanol and 20mL of water are added, the mixture is heated and refluxed and stirred for reaction for 12 hours, the mixture is cooled to room temperature, filtered, washed by water and ethanol, separated and purified by a silica gel column and recrystallized by THF-ethanol to obtain a product CJHP19 (T)2O), yield 78%, MS (MALDI-TOF): m/z 700.2405[ M + H ]]+。
Example 2
Preparation of compounds CJHP 01-CJHP 18, CJHP 20-CJHP 40, CJHP 133-CJHP 138, CJHP145 and CJHP146,
T2a compound of ═ O:
referring to the synthesis of the compound CJHP19 in example 1, the difference is that according to actual needs, different boric acid is used to replace 9-phenanthrene boric acid in the fourth step of example 1, different halogenated compound is used to replace 2-chloro-4, 6-diphenyl-1, 3, 5-triazine in the seventh step of example 1, the mass amount of the compound is changed according to molar weight, and other experimental parameters are adjusted according to actual needs.
T2A compound of ═ S:
referring to the synthesis of the compound CJHP19 in example 1, except that dibenzothiophene-1-boronic acid is used instead of dibenzofuran-1-boronic acid in the first step of example 1, and different boronic acids are used instead of 9-phenanthreneboronic acid in the fourth step of example 1 according to actual needs, different halides are used instead of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine in the seventh step of example 1, and the mass usage of the compound is changed according to molar amounts, and other experimental parameters are adjusted accordingly according to actual needs.
T2＝NAr1The compound of (1):
reference is made to the synthesis of CJHP19 in example 1, except that 9-Ar is used1-4-carbazole boronic acid replaces dibenzofuran-1-boronic acid in the first step of example 1, and different boronic acids are used to replace 9-phenanthrene boronic acid in the fourth step of example 1 according to actual needs, and different boronic acids are usedThe halide of example 1 replaces 2-chloro-4, 6-diphenyl-1, 3, 5-triazine in the seventh step, the mass amount of the compound is changed according to the molar amount, and other experimental parameters are adjusted according to actual needs.
Example 3
Preparation of compound CJHP 42:
Figure BDA0003066560290000211
20.0mmol of intermediate Int-7 (prepared by the synthesis method of reference example 1) was dissolved in 80mL of dry THF, cooled to-78 deg.C under nitrogen, added dropwise to 10.0mL of 2.5M n-butyllithium n-hexane solution, stirred for 1 hour, heated to-50 deg.C, added dropwise to a solution of 25.0mmol of diphenylphosphoryl chloride in THF, stirred for 1 hour, heated to room temperature and stirred for 10 hours, added 50mL of methanol, concentrated to dryness under reduced pressure, the residue was dissolved in 80mL of dichloromethane, added 20mL of 35% hydrogen peroxide, stirred for 12 hours, the organic phase was separated, washed with water, dried, filtered, concentrated to dryness under reduced pressure, and purified by silica gel column separation to give product CJHP42, yield 49%, MS (MALDI-TOF): m/z568.1498[ M]+。
Example 4
The preparation of the compounds CJHP41 and CJHP 43-CJHP 51 is the same as the synthesis of the compound CJHP42 in example 3, except that Int-7 in example 3 is replaced by different compounds according to actual needs, the mass amount of the compounds is changed according to molar weight, and other experimental parameters are adjusted correspondingly according to actual needs.
Example 5
Preparation of compound CJHP 55:
Figure BDA0003066560290000221
20.0mmol of intermediate Int-8 (prepared according to the synthesis method of example 1) was dissolved in 80mL of dry toluene and 16.0mmol of intermediate Int-8 was added under nitrogen protectionN- ([1,1' -Biphenyl)]-2-yl) -9, 9-dimethyl-9H-fluoren-2-amine (CAS:1198395-24-2), 24.0mmol of sodium tert-butoxide, 1.6mmol of cuprous iodide, 0.2mmol of Pd2(dba)3Heating the catalyst and 0.2mL of 10% tri-tert-butylphosphine toluene solution to 100 ℃, stirring for reaction for 10 hours, cooling to room temperature, adding 50mL of water, stirring for reaction for 1 hour, filtering, washing the cake with water, performing ethanol, and separating and purifying the yellow solid by using a silica gel column to obtain a product CJHP55 with the yield of 84%, and MS (MALDI-TOF): m/z 652.2658[ M + H ]]+。
Example 6
The preparation of CJHP 52-CJHP 54 and CJHP 56-CJHP 71 is the same as that of CJHP55 in example 5, except that N- ([1,1' -biphenyl ] -2-yl) -9, 9-dimethyl-9H-fluoren-2-amine in example 5 is replaced by different compounds according to actual needs, the mass amount of the compounds is changed according to molar weight, and other experimental parameters are adjusted according to actual needs.
Example 7
Preparation of compound CJHP91, comprising the following steps:
the first step is as follows: preparation of intermediate Int-14
Figure BDA0003066560290000231
Referring to the first step of the synthesis of example 1, intermediate Int-14 was prepared in 84% yield by replacing only dibenzofuran-1-boronic acid of the first step of example 1 with (9, 9-dimethyl-9H-fluoren-4-yl) boronic acid (CAS: 1246022-50-3).
The second step is that: preparation of intermediate Int-15
Figure BDA0003066560290000232
Referring to the second step synthesis of example 1, intermediate Int-15 was prepared in 96% yield by replacing Int-14 with Int-1 only in the second step of example 1.
The third step: preparation of intermediate Int-16
Figure BDA0003066560290000233
Referring to the synthesis procedure of the third step of example 1, intermediate Int-16 was prepared in 92% yield by replacing only Int-2 of the third step of example 1 with Int-15.
The fourth step: preparation of intermediate Int-17
Figure BDA0003066560290000241
Referring to the fourth synthesis step of example 1, intermediate Int-17 was prepared in 88% yield by replacing only Int-3 and 9-phenanthreneboronic acid with Int-16 and phenylboronic acid (CAS:98-80-6) in the fourth step of example 1.
The fifth step: preparation of intermediate Int-18
Figure BDA0003066560290000242
Referring to the synthesis procedure of the third step of example 1, intermediate Int-18 was prepared in a yield of 95% by replacing only Int-2 of the third step of example 1 with Int-17.
And a sixth step: preparation of compound CJHP91
Figure BDA0003066560290000243
10.0mmol of Int-18, 12.0mmol of naphtho [2,3-b ]]Benzofuran-1-boronic acid (CAS:2261008-21-1), 30.0mmol of potassium phosphate hydrate and 58.0mg of Pd (PPh)3)4Adding 40mL of toluene, 20mL of ethanol and 20mL of water into the catalyst, heating, refluxing, stirring and reacting for 12 hours, cooling to room temperature, filtering, washing a filter cake with water and ethanol, separating and purifying by using a silica gel column, and recrystallizing by using toluene-THF to obtain a product CJHP91 with the yield of 82%, wherein MS (MALDI-TOF): m/z 611.2389[ M + H ]]+。
Example 8
The synthesis method of the compounds CJHP 72-CJHP 90, CJHP 92-CJHP 103, CJHP111, CJHP112, CJHP 139-CJHP 144, CJHP147 and CJHP148 is the same as the preparation of the compound CJHP91 in example 7, except that different compounds are used in place of phenylboronic acid in the fourth step in example 7 and in place of naphtho [2,3-b ] benzofuran-1-boronic acid in the sixth step in example 7 according to actual needs, and the mass amounts of the compounds are changed according to molar amounts, and other experimental parameters are adjusted accordingly according to actual needs.
Example 9
Preparation of compound CJHP 119:
Figure BDA0003066560290000251
under nitrogen protection, 12.0mmol of intermediate Int-9, 10.0mmol of N- (9, 9-dimethyl-9H-fluoren-2-yl) -9,9' -spirobifluoren-2-amine (CAS:1364602-61-8), 1.5g of sodium tert-butoxide and 0.21g of cuprous iodide, 0.7mg of Pd2(dba)3CHCl3And 0.1mL of 10% tri-tert-butylphosphine toluene solution, 60mL of dried toluene was added, the mixture was heated to 100 ℃ and stirred for reaction for 12 hours, the mixture was cooled to room temperature, filtered, the filter cake was washed with water and ethanol, and then separated and purified by a silica gel column, and then recrystallized by methylene chloride-tetrahydrofuran to obtain CJHP119 with a yield of 82%, MS (MALDI-TOF): m/z 840.3648[ M + H ]]+。
Example 10
The synthesis method of the compounds CJHP 114-CJHP 118 and CJHP 120-CJHP 132 is the same as that of the compound CJHP119 in example 9, except that N- (9, 9-dimethyl-9H-fluoren-2-yl) -9,9' -spirobifluorene-2-amine in example 9 is replaced with a different compound according to actual needs, the mass amount of the compound is changed according to molar weight, and other experimental parameters are adjusted according to actual needs.
Example 11
Preparation of compound CJHP 104:
Figure BDA0003066560290000261
referring to the synthesis method of example 3, replacing only Int-7 in example 3 with Int-20, compound CJHP104 was prepared in 74% yield, MS (MALDI-TOF): m/z 692.2518[ M + H ]]+。
Example 12
The synthesis method of the compounds CJHP 105-CJHP 110 and CJHP113 is the same as the preparation of the compound CJHP104 in example 11, except that Int-20 in example 11 is replaced by different compounds according to actual needs, the mass amount of the compounds is changed according to molar weight, and other experimental parameters are adjusted according to actual needs.
Test example 1
The compounds prepared in examples 1 to 12 were sublimated and purified to prepare an organic electroluminescent device, and the specific preparation method was as follows:
(1) the ITO-coated glass substrate is ultrasonically washed by distilled water, ultrasonically washed by mixed solvent of isopropanol and acetone/ethanol, baked in clean environment to be completely dried, irradiated by an ultraviolet light cleaning machine for 10 minutes, cleaned by UV for 5 minutes, and transferred to a vacuum evaporation machine.
(2) HT002 (eight billion space-time) is laminated on the processed ITO electrode in sequence,
Figure BDA0003066560290000262
) HT022 (eight billion space-time,
Figure BDA0003066560290000268
) HT001 (space-time-of-billion,
Figure BDA0003066560290000263
) ADN + 10% DA021 (billionth space-time,
Figure BDA0003066560290000264
) cJHP 01-CJHP 148 compounds
Figure BDA0003066560290000265
/LiF
Figure BDA0003066560290000266
/Al
Figure BDA0003066560290000267
An organic electroluminescent element was produced.
Comparative example 1
An organic electroluminescent element was prepared in the same manner as in test example 1 except that Alq3 (8-hydroxyquinoline aluminum) was used as an electron transporting layer material instead of the compounds CJHP01 to CJHP 148.
Comparative example 2
An organic electroluminescent element was prepared in the same manner as in test example 1 except that the compounds CJHP01 to CJHP148 were not used as the electron transporting layer material.
Wherein the structural formulas of ADN and Alq3 are shown as follows:
Figure BDA0003066560290000271
for the organic electroluminescent elements prepared in test example 1 and comparative examples 1 to 2, the current density was measured to be 10mA/cm2The driving voltage, current efficiency, emission peak, part of the compounds, and the test results of the organic electroluminescent elements prepared in comparative examples 1 to 2 are shown in table 1.
TABLE 1
Test compounds Drive voltage (V) Maximum peak (nm) Current efficiency (cd/A)
CJHP09 4.24 466 7.85
CJHP19 3.95 465 7.15
CJHP28 4.16 466 7.80
CJHP42 3.72 466 7.46
CJHP44 3.85 465 7.74
CJHP50 3.56 466 7.02
CJHP94 4.58 466 7.91
CJHP104 4.27 466 7.73
CJHP138 3.86 466 7.69
CJHP146 3.54 466 7.62
Comparative example 1 4.83 465 6.42
Comparative example 2 4.96 466 5.85
As can be seen from table 1, the organic electroluminescent element using the compound prepared according to the present invention for the electron transport layer showed excellent properties in terms of driving voltage, current efficiency, and the strongest peak of light emission, as compared to the organic electroluminescent element using Alq3 for the electron transport layer and the organic electroluminescent element without the electron transport layer.
The results of the testing of the other compounds are essentially consistent with the data in Table 1, and are not listed due to space limitations.
Test example 2
An organic electroluminescent element was produced in the same manner as in test example 1 except that compounds CJHP01 to CJHP148 were used as host materials of the light-emitting layer instead of ADN in test example 1 and CJHP50 was used as a material of the electron-transporting layer.
The organic electroluminescent element prepared in test example 2 was measured for its current density of 10mA/cm2The driving voltage, current efficiency, and emission peak of the compound are shown in Table 2.
TABLE 2
Test compounds Drive voltage (V) Maximum peak (nm) Current efficiency (cd/A)
CJHP03 3.62 466 7.88
CJHP10 3.58 466 7.39
CJHP14 3.54 466 7.46
CJHP29 3.60 466 7.75
CJHP83 4.11 466 7.96
CJHP91 4.05 466 7.91
ADN 3.56 466 7.02
As can be seen from table 2, the organic electroluminescent element using the compound of the present invention for the host material of the light emitting layer showed superior performance in terms of driving voltage, current efficiency, and the most intense peak of light emission, as compared to ADN.
The results of the testing of the other compounds are essentially consistent with the data in Table 2, and are not listed due to space limitations.
Test example 3
An organic electroluminescent element was prepared in the same manner as in test example 1 except that the electron blocking layer material used was the compounds CJHP01 to CJHP148 instead of HT001 in test example 1 and CJHP50 was used as the electron transporting layer material.
The organic electroluminescent element produced in test example 3 was measured for its current density of 10mA/cm2The driving voltage, current efficiency, and emission peak of the compound are shown in Table 3.
TABLE 3
Test compounds Drive voltage (V) Maximum peak (nm) Current efficiency (cd/A)
CJHP55 3.48 466 7.28
CJHP60 3.46 466 7.26
CJHP116 3.53 466 7.10
CJHP119 3.57 466 7.18
CJHP128 3.55 466 7.12
HT001 3.58 466 7.05
As can be seen from table 3, the organic electroluminescent element using the compound of the present invention for an electron blocking layer material showed superior performance in terms of driving voltage, current efficiency, and the most intense peak of light emission, compared to HT 001.
The results of the testing of the other compounds are essentially consistent with the data in Table 3, and are not listed due to space limitations.
In summary, the organic electroluminescent element prepared from the compound of the present invention can be used in a flat light emitting body such as a mobile phone, a wall-mounted television, a flat panel display, and a lighting, a light source such as a backlight of a copier, a printer, a liquid crystal display, and a measuring instrument, a display panel, a marker lamp, and the like.
The above description is only for the specific embodiments of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art can easily conceive of the changes or substitutions within the technical scope of the present invention, and all the changes or substitutions should be covered within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the appended claims.

Claims (10)

1. An organic compound having a formula of formula (I):
Figure FDA0003066560280000011
wherein G is selected from O, S, NAr1Or CR13R14；
R1～R14Each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40Alkyl of (C)2-C40Alkenyl of, C2-C40Alkynyl of (A), C3-C40Cycloalkyl of (2), heterocycloalkyl of atomic number 3 to 40, C6-C60Aryl of (C)2-C60Heteroaryl of (A), C1-C40Alkoxy group of (C)6-C60Aryloxy group of (A), C1-C40Alkylsilyl group of (C)6-C60Arylsilyl group of (C)1-C40Alkyl boron group of (2), C6-C60Aryl boron group of (1), C6-C60Aryl phosphorus radical of (2), C6-C60Aryl phosphorus oxide group of (1), C6-C60Any two or more adjacent substituents may be optionally joined or fused, or bridged to each other by a bridging group bonded to the same nitrogen atom, phosphorus atom, boron atom, oxygen, or sulfur, forming a single ring or a fused ring;
Ar1selected from the group consisting of C6-C60Aryl of (C)2-C60Heteroaryl of (A), C6-C60Aryl boron group of (1), C6-C60Aryl phosphorus radical of (2), C6-C60Aryl phosphorus oxide group of (2) and C6-C60Arylamine groups of (a).
2. The organic compound of claim 1, wherein C is2-C60The heteroaryl group of (a) is one of the following structures:
Figure FDA0003066560280000012
Figure FDA0003066560280000021
wherein Z is1、Z2Each independently selected from hydrogen, deuterium, a halogen atom, a hydroxyl group, a nitrile group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a carboxylate thereof, a sulfonic group or a sulfonate thereof, a phosphoric group or a phosphate thereof, C1-C40Alkyl radical, C2-C40Alkenyl radical, C2-C40Alkynyl, C1-C40Alkoxy radical,C3-C40Cycloalkyl radical, C3-C40Cycloalkenyl radical, C6-C60Aryl radical, C6-C60Aryloxy radical, C6-C60Aryl boron group of (1), C6-C60Aryl phosphorus radical of (2), C6-C60Aryl phosphorus oxide group of (1), C6-C60Arylamino or C of2-C60One of the heteroaryl groups of (a);
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;
T1represents oxygen, sulfur, CR15R16Or NAr2；
The R is15And R16Each independently selected from hydrogen, deuterium, C1-C40Alkyl of (C)2-C40Alkenyl of, C2-C40Alkynyl of (A), C3-C40Cycloalkyl of (2), heterocycloalkyl of atomic number 3 to 40, C6-C60Aryl of (C)2-C60Heteroaryl of (a);
ar is2Selected from the group consisting of C6-C60Aryl of (C)2-C60Heteroaryl of (A), C6-C60Aryl boron group of (1), C6-C60Aryl phosphorus radical of (2), C6-C60Aryl phosphorus oxide group of (2) and C6-C60Arylamine groups of (a);
Figure FDA0003066560280000022
represents a bond between a substituent and the main structure.
3. An organic compound according to claim 1, wherein G is selected from O, S or CR13R14；
R1～R14Each independently selected from hydrogen, deuterium, C1-C40Alkyl of (C)6-C60Aryl of (C)2-C60Heteroaryl of (A), C6-C60Aryl phosphorus radical of (2), C6-C60Aryl phosphorus oxide group of (1), C6-C60Arylamine groups of (a).
4. The organic compound according to any one of claims 1 to 3, wherein the heteroaryl group is selected from the group consisting of pyrimidine, pyrazine, triazine, imidazole, benzimidazole, phenanthroimidazole, imidazopyridine, triazolopyridine and quinazoline;
preferably, the pyrimidine, pyrazine, triazine, imidazole, benzimidazole, phenanthroimidazole, imidazopyridine, triazolopyridine and quinazoline may each be independently deuterium, halogen atom, cyano group, nitro group, C1-C40Alkyl of (C)2-C40Alkenyl of, C2-C40Alkynyl of (A), C3-C40Cycloalkyl of, C3-C40Heterocycloalkyl of (A), C6-C60Aryl of (C)2-C60Heteroaryl of (A), C1-C40Alkoxy group of (C)6-C60Aryloxy group of (A), C1-C40Alkylsilyl group of (C)6-C60Arylsilyl group of (C)1-C40Alkyl boron group of (2), C6-C60Aryl boron group of (1), C6-C60Aryl phosphorus radical of (2), C6-C60Aryl phosphorus oxide group of (2) and C6-C60When the substituent is plural, plural substituents may be the same as or different from each other.
5. The organic compound of any one of claims 1 to 4, wherein the organic compound is one of CJHP 01-CJHP 148, and has a specific structural formula as follows:
Figure FDA0003066560280000031
Figure FDA0003066560280000041
Figure FDA0003066560280000051
Figure FDA0003066560280000061
Figure FDA0003066560280000071
Figure FDA0003066560280000081
wherein, T2is-O-, -S-, or one of the following structures:
Figure FDA0003066560280000091
T3is-O-, -S-, or one of the following structures:
Figure FDA0003066560280000092
and represents a bond.
6. An organic electroluminescent material comprising the organic compound according to any one of claims 1 to 5.
7. An organic electroluminescent element comprising a first electrode, a second electrode and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layer comprises the organic compound according to any one of claims 1 to 5.
8. The organic electroluminescent element according to claim 7, wherein the organic layer is a light-emitting layer, an electron-transporting layer, an electron-injecting layer, a hole-transporting layer or an electron-blocking layer.
9. The organic electroluminescent element according to claim 8, wherein the organic compound is a substance of a light-emitting layer.
10. The organic electroluminescent element according to claim 8, wherein the organic compound is a substance of an electron transport layer.
CN202110527450.6A 2021-05-14 2021-05-14 Organic compound, organic electroluminescent material and organic electroluminescent element Pending CN113248477A (en)

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