CN117447383A - Aromatic amine organic compound and organic electroluminescent device prepared from same - Google Patents

Aromatic amine organic compound and organic electroluminescent device prepared from same Download PDF

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CN117447383A
CN117447383A CN202210828963.5A CN202210828963A CN117447383A CN 117447383 A CN117447383 A CN 117447383A CN 202210828963 A CN202210828963 A CN 202210828963A CN 117447383 A CN117447383 A CN 117447383A
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substituted
unsubstituted
group
naphthyl
phenyl
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尚书夏
王芳
崔明
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Jiangsu Sunera Technology Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/96—Spiro-condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

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  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

The invention discloses an arylamine organic compound and an organic electroluminescent device prepared from the same, and belongs to the technical field of semiconductor materials. The structure of the compound is shown as a general formula (1):

Description

Aromatic amine organic compound and organic electroluminescent device prepared from same
Technical Field
The invention relates to the technical field of semiconductor materials, in particular to an arylamine organic compound and an organic electroluminescent device prepared from the same.
Background
The organic electroluminescent (OLED: organic Light Emission Diodes) device technology can be used for manufacturing novel display products and novel illumination products, is hopeful to replace the existing liquid crystal display and fluorescent lamp illumination, and has wide application prospect. The OLED light-emitting device is like a sandwich structure and comprises electrode material film layers and organic functional materials clamped between the different electrode material film layers, wherein various different organic functional materials are mutually overlapped together according to purposes to jointly form the OLED light-emitting device. When voltage is applied to two end electrodes of the OLED light-emitting device as a current device, positive and negative charges in the organic layer functional material film layer act through an electric field, and the positive and negative charges are further compounded in the light-emitting layer, so that OLED electroluminescence is generated.
At present, the OLED display technology has been applied to the fields of smart phones, tablet computers and the like, and further expands to the large-size application fields of televisions and the like, but compared with the actual product application requirements, the OLED display technology has the advantages that the luminous efficiency, the service life and the like of the OLED device are further improved. The studies on the improvement of the performance of the OLED light emitting device include: the driving voltage of the device is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the like. In order to realize the continuous improvement of the performance of the OLED device, not only is the innovation of the structure and the manufacturing process of the OLED device needed, but also the continuous research and innovation of the OLED photoelectric functional material are needed, and the functional material of the OLED with higher performance is created.
Blue organic electroluminescent devices are always soft ribs in full-color OLED development, so that the efficiency, service life and other performances of blue light devices are not fully improved until now, and therefore, how to improve the performances of the devices is still a critical problem and challenge in the field. Since the blue light host materials currently used in the market are mostly electron-biased host materials, the hole transport materials are required to have excellent hole transport properties in order to adjust the carrier balance of the light emitting layer. The better the hole injection and transmission, the more the adjusting composite area is deviated to the side far away from the electron blocking layer, so that the light is emitted far away from the interface, the performance of the device is improved, and the service life of the device is prolonged. Therefore, the hole transport region material is required to have high hole injection property, high hole mobility, high electron blocking property, and high electron weatherability.
In the prior art, in a high-temperature environment, as the difference between electron mobility and hole mobility is more obvious, a blue light device shows rich electrons and holes and has poor service life in the high-temperature environment, and in order to improve the high-temperature service life of the blue light device, the mobility of a hole transport material, especially the mobility under the high-temperature condition, needs to be improved.
Disclosure of Invention
In view of the above problems in the prior art, the applicant provides an arylamine organic compound and an organic electroluminescent device prepared from the same. The organic compound has excellent hole transport capability and thermal stability, and can simultaneously show the effects of improving the efficiency (index) of the device and prolonging the service life of the device, in particular prolonging the high-temperature service life of the device when the aromatic amine organic compound is used for forming the hole transport material of the organic electroluminescent device.
The technical scheme of the invention is as follows: an arylamine organic compound has a structure shown in a general formula (1):
in the general formula 1, R 1 To R 12 Are each independently represented by formula A, a hydrogen atom, a phenyl group, a methyl group, a deuterated tert-butyl group, a tert-butyl group, an adamantyl group, a naphthyl group, wherein R 1 To R 12 At least one of which is represented by formula A;
when R is 1 -R 12 When the compound is represented by phenyl or naphthyl, R 1 -R 12 The connection mode with the benzene ring can be single bond connection or parallel ring connection;
R 0 represented by methyl, ethyl, t-butyl, phenyl, biphenyl, naphthyl, benzofuranyl or benzothiaA phenone group;
in formula A, the Ar 1 And Ar is a group 2 Each independently represents a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted 5-30 membered heteroaryl;
said L, L 1 、L 2 Each independently represents a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted 5-30 membered heteroarylene group;
the substituents of the foregoing substituted or unsubstituted groups are each optionally selected from deuterium atoms, methyl, deuterated methyl, ethyl, t-butyl, adamantyl, C6-C30 aryl or 5-30 membered heteroaryl;
the hetero atom in the heteroaryl is selected from one or more of oxygen atom, sulfur atom or nitrogen atom.
Preferably, the structure of the organic compound is shown in any one of the general formulas (1-1) to (1-6):
in the general formulae (1-1) to (1-6), R 1 To R 12 Each independently represents a hydrogen atom, phenyl, methyl, deuterated tert-butyl, adamantyl, naphthyl;
when R is 1 -R 12 When the compound is represented by phenyl or naphthyl, R 1 -R 12 The connection mode with the benzene ring can be single bond connection or parallel ring connection;
R 0 represented by methyl, ethyl, t-butyl, phenyl, biphenyl, naphthyl, benzofuranyl or benzothienyl;
the Ar is as follows 1 And Ar is a group 2 Each independently represents a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted 5-30 membered heteroaryl;
the L represents a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted 5-30 membered heteroarylene group;
the substituents of the foregoing substituted or unsubstituted groups are each optionally selected from deuterium atoms, methyl, deuterated methyl, ethyl, t-butyl, adamantyl, C6-C30 aryl or 5-30 membered heteroaryl;
the hetero atom in the heteroaryl is selected from one or more of oxygen atom, sulfur atom or nitrogen atom.
Preferably, the structure of the organic compound is shown in any one of the general formulas (1-1) to (1-6);
in the general formulae (1-1) to (1-6), R 1 To R 12 Each independently represents a hydrogen atom, phenyl, methyl, deuterated methyl, tertiary butyl, adamantyl, naphthyl;
when R is 1 -R 12 When the compound is represented by phenyl or naphthyl, R 1 -R 12 The connection mode with the benzene ring can be single bond connection or parallel ring connection;
R 0 represented by methyl, ethyl, t-butyl, phenyl, biphenyl, naphthyl, benzofuranyl or benzothienyl;
The Ar is as follows 1 And Ar is a group 2 Each independently represents one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted piperonyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted indolo-cyclic group;
the L represents one of single bond, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted furyl, substituted or unsubstituted benzofuranyl and substituted or unsubstituted benzothienyl;
the substituent of the above-mentioned substituted or unsubstituted group is selected from one or several of deuterium atom, methyl, deuterated methyl, ethyl, tertiary butyl, adamantyl, phenyl, biphenyl, naphthyl, pyridyl and naphthyridinyl.
Preferably, the structure of the organic compound is shown in any one of the general formulas (1-7) to (1-9):
in the general formulae (1-7) to (1-9), the R 0 、Ar 1 Ar, ar 2 The meaning of (2) is as described above;
the L represents one of single bond, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted furyl, substituted or unsubstituted benzofuranyl and substituted or unsubstituted benzothienyl;
the substituents of the foregoing substituted or substituted groups are each optionally selected from one or more of deuterium atom, methyl, deuterated methyl, ethyl, tert-butyl, adamantyl, phenyl, naphthyl, biphenyl.
Preferably, the structure of the organic compound is shown in any one of the general formulas (1-10) to (1-11):
in the general formulae (1-10) to (1-11), the Ar 1 And Ar is a group 2 The meaning of (2) is as described above;
the L represents one of single bond, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted furyl, substituted or unsubstituted benzofuranyl and substituted or unsubstituted benzothienyl;
the substituents of the foregoing substituted or substituted groups are each optionally selected from one or more of deuterium atom, methyl, deuterated methyl, ethyl, tert-butyl, adamantyl, phenyl, naphthyl, biphenyl.
Preferably, the structure of the organic compound is shown as a general formula (1-12):
in the general formula (1-12), the Ar 1 And Ar is a group 2 Each independently represents one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted piperonyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted carbazolyl group, and a substituted or unsubstituted indolo-cyclic group.
The substituents of the foregoing substituted or substituted groups are each optionally selected from one or more of deuterium atom, methyl, deuterated methyl, ethyl, tert-butyl, adamantyl, phenyl, naphthyl, biphenyl.
Preferably, the L, L 1 、L 2 Each independently represents a single bond or a structure as shown below:
Any one of them.
The Ar is as follows 1 And Ar is a group 2 Each independently represented by the structure shown below:
any one of them.
Preferably, the formula a is represented by any one of the following structures:
preferably, the specific structure of the organic compound is any one of the following structures:
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the invention also provides an organic electroluminescent device which sequentially comprises an anode, a hole transmission region, a light-emitting region, an electron transmission region and a cathode, wherein the hole transmission region comprises the aromatic amine organic compound.
Preferably, the hole transport region includes a hole injection layer, a hole transport layer, and an electron blocking layer, and the hole transport layer includes the aromatic amine compound.
Preferably, the hole transport region includes a hole injection layer, a hole transport layer, and an electron blocking layer, and the hole injection layer and the hole transport layer include the aromatic amine compound.
The beneficial technical effects of the invention are as follows:
the technical core of the invention is that the arylamine organic compound takes the spirofluorene indole derivative as a core group, and the arylamine groups are connected at different connecting sites, so that the molecule of the invention has the following advantages.
(1) The structure of the aromatic amine hole conducting material has three-dimensional asymmetry, and the asymmetric structure is favorable for keeping a stable amorphous film phase state of molecules during film formation, so that the physical and chemical stability of the film phase state and the film phase state stability under the action of point formation are ensured, and further the service life stability of a device is favorable.
(2) Because the structural characteristics of the arylamine organic compound are favorable for improving the vitrification transfer temperature of molecules and reducing the evaporation temperature of the molecules, namely, even though the molecular weight of the structure is relatively high, the structure can ensure that the structure has relatively low evaporation temperature, the excellent performance is not only favorable for thermal evaporation of materials, but also controls the thermal decomposition rate of the materials, so that the stability of the materials in device application is improved.
(3) The compound disclosed by the invention has higher hole mobility, so that the compound disclosed by the invention is applied as a hole transport material, and can effectively improve the efficiency of a device and reduce the voltage of the device.
Drawings
Fig. 1 is a cross-sectional view of an organic electroluminescent device according to the present invention.
In the figure, 1 represents a substrate layer; 2 represents an anode layer; 3 represents a hole injection layer; 4 represents a hole transport layer; 5 represents an electron blocking layer; 6 represents a light emitting layer; 7 represents a hole blocking layer; 8 represents an electron transport layer; 9 denotes an electron injection layer; 10 is denoted as cathode layer; 11 denotes a cover layer.
Detailed Description
The following description of the embodiments of the present invention will be made clearly and completely with reference to the accompanying drawings, in which it is apparent that the embodiments described are only some embodiments of the present invention, but not all embodiments. The following description of at least one exemplary embodiment is merely exemplary in nature and is in no way intended to limit the invention, its application, or uses. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
In the present invention, when a layer or element is referred to as being "on" another layer or substrate, it can be directly on the other layer or substrate or intervening layers may also be present. Further, it will also be understood that when a layer is referred to as being "between" two layers, it can be the only layer between the two layers or one or more intervening layers may also be present. Like numbers refer to like elements throughout.
In the present invention, when describing electrodes and organic electroluminescent devices, as well as other structures, words of "upper", "lower", "top" and "bottom", etc., which are used to indicate orientations, indicate only orientations in a certain specific state, and do not mean that the relevant structure can only exist in the orientations; conversely, if the structure can be repositioned, for example inverted, the orientation of the structure is changed accordingly. Specifically, in the present invention, the "bottom" side of an electrode refers to the side of the electrode that is closer to the substrate during fabrication, while the opposite side that is farther from the substrate is the "top" side.
In this specification, the term "substituted" means that one or more hydrogen atoms on a given atom or group is replaced by the specified group, provided that the normal valence of the given atom is not exceeded in the present case.
In this specification, the hole feature refers to a feature that can supply electrons when an electric field is applied and is attributed to a conductive feature according to the Highest Occupied Molecular Orbital (HOMO) level, and holes formed in the anode are easily injected into and transported in the light emitting layer.
In this specification, the electron feature refers to a feature that can accept electrons when an electric field is applied and is attributed to a conductive feature according to the Lowest Unoccupied Molecular Orbital (LUMO) level, electrons formed in the cathode are easily injected into and transported in the light emitting layer.
The organic electroluminescent device of the present invention may be a bottom-emission organic electroluminescent device, a top-emission organic electroluminescent device, and a stacked organic electroluminescent device, and is not particularly limited.
In the organic electroluminescent device of the present invention, any substrate commonly used for organic electroluminescent devices may also be used. Examples thereof are transparent substrates such as glass or transparent plastic substrates; an opaque substrate such as a silicon substrate; a flexible Polyimide (PI) film substrate. Different substrates have different mechanical strength, thermal stability, transparency, surface smoothness, and water repellency. The use direction of the substrate is different according to the property of the substrate. In the present invention, a transparent substrate is preferably used. The thickness of the substrate is not particularly limited.
Anode
Preferably, the anode may be formed on the substrate. In the present invention, the anode and the cathode are opposite to each other. The anode may be made of a conductor having a higher work function to aid hole injection, and may be, for example, a metal such as nickel, platinum, copper, zinc, silver, or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals and metal oxides, such as ZnO with Al or ITO with Ag; conductive polymers such as poly (3-methylthiophene), poly (3, 4- (ethylene-1, 2-dioxy) thiophene), and polyaniline, but are not limited thereto. The thickness of the anode depends on the material used, and is generally 50 to 500nm, preferably 70 to 300nm, and more preferably 100 to 200nm.
Cathode electrode
The cathode may be made of a conductor having a lower work function to aid electron injection, and may be, for example, a metal or an alloy thereof, such as magnesium, calcium, sodium, potassium, titanium, indium, aluminum, silver, tin, and combinations thereof; multilayer structural materials, such as LiF/Al, li 2 O/Al and BaF 2 /Ca, but is not limited thereto. The thickness of the cathode is generally 10-50nm, preferably 15-20nm, depending on the material used.
Light emitting region
In the present invention, the light emitting region may be disposed between the anode and the cathode, and may include at least one host material and at least one guest material. As the host material and the guest material of the light-emitting region of the organic electroluminescent device of the present invention, a light-emitting layer material for an organic electroluminescent device known in the art can be used. The host material may be, for example, a thiazole derivative, a benzimidazole derivative, a polydialkylfluorene derivative, or 4,4' -bis (9-Carbazolyl) Biphenyl (CBP). As host material, compounds containing anthracene groups can be used. The guest material may be, for example, quinacridone, coumarin, rubrene, perylene and derivatives thereof, benzopyran derivatives, rhodamine derivatives or aminostyrene derivatives.
In a preferred embodiment of the invention, one or two host material compounds are contained in the light-emitting region.
In a preferred embodiment of the invention, the host material of the light-emitting region used is selected from one or more of the following compounds BH-1-BH-11:
in the present invention, the light emitting region may include a phosphorescent or fluorescent guest material to improve fluorescence or phosphorescence characteristics of the organic electroluminescent device. Specific examples of the phosphorescent guest material include metal complexes of iridium, platinum, and the like, and as the fluorescent guest material, those generally used in the art can be used. In a preferred embodiment of the present invention, the guest material of the light-emitting film layer used is selected from one of the following compounds BD-1 to BD-10:
in the light-emitting region of the present invention, the ratio of host material to guest material used is 99:1 to 70:30, preferably 99:1 to 85:15 and more preferably 97:3 to 87:13 on a mass basis.
The thickness of the light emitting region may be 10 to 50nm, preferably 15 to 30nm, but the thickness is not limited to this range.
Hole transport region
In the organic electroluminescent device of the present invention, a hole transport region is disposed between the anode and the light emitting region, and includes a hole injection layer, a hole transport layer, and an electron blocking layer.
Hole injection layer
The hole injection material used in the hole injection layer (also referred to as an anode interface buffer layer) is a material capable of sufficiently accepting holes from the anode at a low voltage, and the Highest Occupied Molecular Orbital (HOMO) of the hole injection material is preferably a value between the work function of the anode material and the HOMO of the adjacent organic material layer. In a preferred embodiment of the present invention, the hole injection layer is a mixed film of host organic material and P-type dopant material. In order to enable holes to be smoothly injected into the organic film layer from the anode, the HOMO energy level of the main organic material and the P-type doping material must have certain characteristics, so that the occurrence of a charge transfer state between the main material and the doping material is expected to be realized, ohmic contact between the hole injection layer and the anode is realized, and efficient injection of holes from the electrode to the hole injection layer is realized. This feature is summarized as: the difference between the HOMO energy level of the host material and the LUMO energy level of the P-type doped material is less than or equal to 0.4eV. Therefore, for hole host materials with different HOMO energy levels, different P-type doping materials are required to be selected to be matched with the hole host materials, so that ohmic contact of an interface can be realized, and the hole injection effect is improved.
Preferably, specific examples of the host organic material include: metalloporphyrin, oligothiophene, arylamine organic materials, hexanitrile hexaazabenzophenanthrene, quinacridone organic materials, perylene organic materials, anthraquinone, polyaniline and polythiophene conductive polymers; but is not limited thereto.
Preferably, the P-type dopant material is a compound having charge conductivity selected from the group consisting of: quinone derivatives or metal oxides such as tungsten oxide and molybdenum oxide, but are not limited thereto.
In a preferred embodiment of the invention, the P-type doping material used is selected from any of the following compounds P-1 to P-8:
in one embodiment of the invention, the ratio of host organic material to P-type dopant material used is 99:1 to 95:5, preferably 99:1 to 97:3, on a mass basis.
In a preferred embodiment of the present invention, the hole injection layer is a mixed film layer of the organic compound of the present invention and the P-type dopant material.
The thickness of the hole injection layer of the present invention may be 5 to 20nm, preferably 8 to 15nm, but the thickness is not limited to this range.
Hole transport layer
In the organic electroluminescent device of the present invention, a hole transport layer may be disposed over the hole injection layer. The hole transport material is suitably a material having a high hole mobility, which can accept holes from the anode or the hole injection layer and transport the holes into the light emitting layer. In a preferred embodiment, the hole transport layer comprises the same organic compound of the present invention represented by the general formula (1) as the hole injection layer.
The thickness of the hole transport layer of the present invention may be 80, 100 or 200nm, preferably 100 to 150nm, but the thickness is not limited to this range.
Electron blocking layer
In the organic electroluminescent device of the present invention, an electron blocking layer may be disposed between the hole transport layer and the light emitting layer, and particularly contact the light emitting layer. The electron blocking layer is disposed to contact the light emitting layer, and thus, hole transfer at the interface of the light emitting layer and the hole transporting layer can be precisely controlled. In one embodiment of the invention, the electron blocking layer material is selected from carbazole-based aromatic amine derivatives. The thickness of the electron blocking layer may be 5 to 20nm, preferably 8 to 15nm, but the thickness is not limited to this range.
Electron transport region
In the organic electroluminescent device of the present invention, an electron transport region is disposed between the light emitting region and the cathode, and includes a hole blocking layer, an electron transport layer, and an electron injection layer, but is not limited thereto.
Electron injection layer
The electron injection layer may be disposed between the electron transport layer and the cathode. The electron injection layer material is generally a material preferably having a low work function so that electrons are easily injected into the organic functional material layer. Preferably, the electron injection layer material is an N-type metal material. As the electron injection layer material of the organic electroluminescent device of the present invention, electron injection layer materials for organic electroluminescent devices known in the art, for example, lithium; lithium salts such as lithium 8-hydroxyquinoline, lithium fluoride, lithium carbonate or lithium azide; or cesium salts, cesium fluoride, cesium carbonate or cesium azide. The thickness of the electron injection layer of the present invention may be 0.1 to 5nm, preferably 0.5 to 3nm, and more preferably 0.8 to 1.5nm, but the thickness is not limited to this range.
Electron transport layer
The electron transport layer may be disposed over the light emitting film layer or (if present) the hole blocking layer. The electron transport layer material is a material that easily receives electrons of the cathode and transfers the received electrons to the light emitting layer. Materials with high electron mobility are preferred. Examples of the electron transport layer material used for the organic electroluminescent device of the present invention include metal complexes of hydroxyquinoline derivatives such as Alq3, BAlq and LiQ, various rare earth metal complexes, triazole derivatives, triazine derivatives such as 2, 4-bis (9, 9-dimethyl-9H-fluoren-2-yl) -6- (naphthalen-2-yl) -1,3, 5-triazine (CAS. RTM. 1459162-51-6), and imidazole derivatives such as 2- (4- (9, 10-bis (naphthalen-2-yl) anthracene-2-yl) phenyl) -1-phenyl-1H-benzo [ d ] imidazole (CAS. RTM. 561064-11-7, commonly referred to as LG 201), and the like.
In a preferred embodiment of the invention, the electron transport layer also comprises other compounds conventionally used in electron transport layers, for example Alq3, liQ, preferably LiQ.
The thickness of the electron transport layer of the present invention may be 10 to 80nm, preferably 20 to 60nm, and more preferably 25 to 45nm, but the thickness is not limited to this range.
Cover layer
In order to improve the light-emitting efficiency of the organic electroluminescent device, a light extraction layer (i.e., a CPL layer, also referred to as a capping layer) may be further added to the cathode of the device. According to the optical absorption and refraction principles, the higher the refractive index of the CPL cover layer material is, the better the CPL cover layer material is, and the smaller the light absorption coefficient is, the better the CPL cover layer material is. Any material known in the art may be used as the CPL layer material, such as Alq3, or N4, N4' -diphenyl-N4, N4' -bis (9-phenyl-3-carbazolyl) biphenyl-4, 4' -diamine. The CPL coating typically has a thickness of 5-300nm, preferably 20-100nm and more preferably 40-80nm.
The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure that prevents foreign substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass can or a metal can; or a thin film covering the entire surface of the organic layer.
The method of manufacturing an organic electroluminescent device according to the present invention comprises sequentially laminating an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an organic film layer, an electron transport layer, an electron injection layer, and a cathode, and optionally a capping layer, on a substrate. In this regard, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, or LITI may be used, but are not limited thereto. In the present invention, the respective layers are preferably formed by a vacuum vapor deposition method. The individual process conditions in the vacuum evaporation process can be routinely selected by those skilled in the art according to the actual needs.
Synthetic examples
Synthesis of intermediate M-1
Step (1)
Step (2)/>
Step (3)
(1) In a three-necked flask, under the protection of nitrogen, 0.01mol of raw material A-1,0.012mol of raw material B-1 and 150ml of toluene are added and mixed under stirring, and then 5X 10 is added -5 mol Pd 2 (dba) 3 ，5×10 -5 Heating 0.03mol of tri-tert-butyl phosphorus and 0.03mol of sodium tert-butoxide to 105 ℃, and carrying out reflux reaction for 22 hours, wherein a sampling point plate shows that no amino compound remains and the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction is present, and passing through neutral silica gel column to obtain intermediate C-1.
(2) Under nitrogen atmosphere, 0.06mol of intermediate C-1 was added to a three-necked flask, and a mixed solvent (300 ml of toluene, 90ml of H was added 2 O) dissolving it, stirring for 1 hr under nitrogen, and slowly adding 0.05mol of raw material D-1 and 0.1mol of K 2 CO 3 、0.005mol Pd(PPh 3 ) 4 The reaction was heated to 90℃and was observed by Thin Layer Chromatography (TLC) for 9 hours until the reaction was complete. Naturally cooling to room temperature, adding water into the reaction system for extraction, separating liquid, and decompressing and rotating the organic phaseSteaming until no fraction is present. The obtained material was purified by silica gel column to obtain intermediate K-1.
(3) To a three-necked flask, 0.06mol of intermediate K-1 and 300mL of anhydrous tetrahydrofuran were added, the mixture was cooled to-78℃under the protection of nitrogen, 0.06mol of a 2.5M N-butyllithium N-hexane solution was slowly dropped, the temperature was kept under stirring for 2 hours, 0.06mol of raw material F-1 was dropped into the solution, the reaction was completed at room temperature for 2 hours, a 1N hydrochloric acid solution was added to the reaction solution, extraction was performed with methylene chloride, drying and concentration were performed, 0.3mL of acetic acid and 0.1mL of concentrated hydrochloric acid were added to the crude product, heating reflux was performed for 5 hours, cooling and filtration were performed, and then ethanol and tetrahydrofuran were used for recrystallization and drying to obtain intermediate M-1.
Intermediate M was prepared in a similar manner as in example 1, as shown in table 1 below:
preparation of intermediate P-1:
step (1)/>
Step (2)
(1) Under nitrogen atmosphere, 0.06mol of raw material H-1 was charged into a three-necked flask, and a mixed solvent (300 ml of toluene, 90ml of H was added 2 O) dissolving it, stirring for 1 hr under nitrogen, and slowly adding 0.05mol of raw material E-1 and 0.1mol of K 2 CO 3 、0.005mol Pd(PPh 3 ) 4 The reaction was heated to 90℃and observed by Thin Layer Chromatography (TLC) for 8 hours until the reaction was complete. Naturally cooling to room temperature, adding water into the reaction system for extraction, separating liquid, and performing reduced pressure rotary evaporation on the organic phase until no fraction exists. The obtained material was purified by silica gel column to obtain intermediate R-1.
(2) In a three-necked flask, under the protection of nitrogen, 0.01mol of raw material G-1,0.012mol of intermediate R-1 and 150ml of methyl were addedMixing benzene with stirring, and adding 5×10 -5 mol Pd 2 (dba) 3 ，5×10 -5 Heating 0.03mol of tri-tert-butyl phosphorus and 0.03mol of sodium tert-butoxide to 105 ℃, and carrying out reflux reaction for 24 hours, wherein a sampling point plate shows that no amino compound remains and the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction is present, and passing through neutral silica gel column to obtain intermediate P-1.
Preparation of intermediate P-6:
step (1)
Step (2)
(1) Under nitrogen atmosphere, 0.06mol of H-2 as a raw material was charged into a three-necked flask, and a mixed solvent (300 ml of toluene, 90ml of H was added 2 O) dissolving it, stirring for 1 hr under nitrogen, and slowly adding 0.05mol of raw material E-2 and 0.1mol of K 2 CO 3 、0.005mol Pd(PPh 3 ) 4 The reaction was heated to 90℃and was observed by Thin Layer Chromatography (TLC) for 9 hours until the reaction was complete. Naturally cooling to room temperature, adding water into the reaction system for extraction, separating liquid, and performing reduced pressure rotary evaporation on the organic phase until no fraction exists. The obtained material was purified by silica gel column to obtain intermediate R-2.
(2) In a three-necked flask, under the protection of nitrogen, 0.01mol of raw material G-1,0.012mol of intermediate R-2 and 150ml of toluene are added and stirred and mixed, and then 5X 10 is added -5 mol Pd 2 (dba) 3 ，5×10 -5 Heating 0.03mol of tri-tert-butyl phosphorus and 0.03mol of sodium tert-butoxide to 105 ℃, and carrying out reflux reaction for 20 hours, wherein a sampling point plate shows that no amino compound remains and the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction exists, and passing through a neutral silica gel column to obtain an intermediate P-6.
Preparation of intermediate P-7:
step (1)/>
Step (2)
(1) Under nitrogen atmosphere, 0.06mol of raw material H-1 was charged into a three-necked flask, and a mixed solvent (300 ml of toluene, 90ml of H was added 2 O) dissolving it, stirring for 1 hr under nitrogen, and slowly adding 0.05mol of raw material E-3 and 0.1mol of K 2 CO 3 、0.005mol Pd(PPh 3 ) 4 The reaction was heated to 90℃and was observed by Thin Layer Chromatography (TLC) for 6 hours until the reaction was complete. Naturally cooling to room temperature, adding water into the reaction system for extraction, separating liquid, and performing reduced pressure rotary evaporation on the organic phase until no fraction exists. The obtained material was purified by silica gel column to obtain intermediate R-3.
(2) In a three-necked flask, under the protection of nitrogen, 0.01mol of raw material G-1,0.012mol of intermediate R-3 and 150ml of toluene are added and stirred and mixed, and then 5X 10 is added -5 mol Pd 2 (dba) 3 ，5×10 -5 Heating 0.03mol of tri-tert-butyl phosphorus and 0.03mol of sodium tert-butoxide to 105 ℃, and carrying out reflux reaction for 18 hours, wherein a sampling point plate shows that no amino compound remains and the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction exists, and passing through a neutral silica gel column to obtain an intermediate P-7.
Preparation of intermediate P-11:
step (1)
Step (2)
(1) Under nitrogen atmosphere, 0.06mol of raw material H-3 was charged into a three-necked flask, and a mixed solvent (300 ml of toluene, 90ml of H was added 2 O) dissolving it, stirring for 1 hr under nitrogen, and slowly adding 0.05mol of raw material E-4 and 0.1mol of K 2 CO 3 、0.005mol Pd(PPh 3 ) 4 Heating to 90 ℃ for 7 hoursThe reaction was observed by Thin Layer Chromatography (TLC) until the reaction was complete. Naturally cooling to room temperature, adding water into the reaction system for extraction, separating liquid, and performing reduced pressure rotary evaporation on the organic phase until no fraction exists. The obtained material was purified by silica gel column to obtain intermediate R-4.
(2) In a three-necked flask, under the protection of nitrogen, 0.01mol of raw material G-2,0.012mol of intermediate R-4 and 150ml of toluene are added and stirred and mixed, and then 5X 10 is added -5 mol Pd 2 (dba) 3 ，5×10 -5 Heating 0.03mol of tri-tert-butyl phosphorus and 0.03mol of sodium tert-butoxide to 105 ℃, and carrying out reflux reaction for 21 hours, wherein a sampling point plate shows that no amino compound remains and the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction exists, and passing through a neutral silica gel column to obtain an intermediate P-11.
Preparation of intermediate P-13:
in a three-necked flask, under the protection of nitrogen, 0.012mol of raw material G-1,0.01mol of raw material H-4 and 150ml of toluene were added and mixed with stirring, and then 5X 10 was added -5 mol Pd 2 (dba) 3 ，5×10 -5 Heating 0.03mol of tri-tert-butyl phosphorus and 0.03mol of sodium tert-butoxide to 105 ℃, and carrying out reflux reaction for 19 hours, wherein a sampling point plate shows that no amino compound remains and the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction is present, and passing through neutral silica gel column to obtain intermediate P-13.
Synthesis of Compound 65
In a three-necked flask, under the protection of nitrogen, 0.01mol of intermediate P-1,0.012mol of intermediate M-1 and 150ml of toluene were added and mixed under stirring, followed by addition of 5X 10 -5 mol Pd 2 (dba) 3 ，5×10 -5 mol of tri-tert-butyl phosphorus, 0.03mol of sodium tert-butoxide, heating to 105 ℃, carrying out reflux reaction for 20 hours, sampling a dot plate, displayingNo amino compound remains and the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction is present, and passing through a neutral silica gel column to obtain compound 65. Elemental analysis structure (molecular formula C) 58 H 40 N 2 ): test value: c,91.02; h,5.29; n,3.68.LC-MS: measurement value: 765.43 ([ M+H)]+)。
The following compounds were prepared in a similar manner to the synthesis of compound 65, involving the starting materials and intermediates as shown in table 2-1 below:
TABLE 2-1
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Synthesis of Compound 207
Step (1)
Step (2)
(1) Under nitrogen atmosphere, 0.06mol of intermediate M-2 was added to a three-necked flask, and the mixed solvent (300 ml of toluene, 90ml of H was added 2 O) dissolving it, stirring for 1 hr under nitrogen, and slowly adding 0.05mol of raw material E-5 and 0.1mol of K 2 CO 3 、0.005mol Pd(PPh 3 ) 4 The reaction was heated to 90℃and was observed by Thin Layer Chromatography (TLC) for 9 hours until the reaction was complete. Naturally cooling to room temperature, adding water into the reaction system for extraction, separating liquid, and performing reduced pressure rotary evaporation on the organic phase until no fraction exists. The obtained material was purified by silica gel column to obtain intermediate N-1.
(2) In a three-necked flask, under the protection of nitrogen, 0.01mol of intermediate P-12,0.012mol of intermediate N-1 and 150ml of toluene were added and mixed under stirring, and then 5X 10 was added -5 mol Pd 2 (dba) 3 ，5×10 -5 Heating 0.03mol of tri-tert-butyl phosphorus and 0.03mol of sodium tert-butoxide to 105 ℃, and carrying out reflux reaction for 22 hours, wherein a sampling point plate shows that no amino compound remains and the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction is obtained, and passing through a neutral silica gel column to obtain the compound 207. The actual measurement value is 842.14; elemental analysis actual measurement: c,89.88; h,5.17; n,4.96.
The following compounds were prepared in a similar manner to the synthesis of compound 207, involving the starting materials and intermediates as shown in tables 2-2 below:
TABLE 2-2
Synthesis of Compound 262
/>
(1) Under nitrogen atmosphere, 0.06mol of intermediate M-4 was added to a three-necked flask, and the mixed solvent (300 ml of toluene, 90ml of H was added 2 O) dissolving it, stirring for 1 hr under nitrogen, and slowly adding 0.05mol of raw material E-7 and 0.1mol of K 2 CO 3 、0.005mol Pd(PPh 3 ) 4 The reaction was heated to 90℃and was observed by Thin Layer Chromatography (TLC) for 6 hours until the reaction was complete. Naturally cooling to room temperature, adding water into the reaction system for extraction, separating liquid, and performing reduced pressure rotary evaporation on the organic phase until no fraction exists. The obtained material was purified by silica gel column to obtain intermediate N-2.
(2) In a three-necked flask, under the protection of nitrogen, 0.01mol of raw material P-3,0.012mol of intermediate N-2 and 150ml of toluene are added and stirred and mixed, and then 5X 10 is added -5 mol Pd 2 (dba) 3 ，5×10 -5 mol of tri-tert-butyl-phosphorus, 0.03mol of tert-butyl-alcoholHeating sodium to 105 ℃, carrying out reflux reaction for 20 hours, sampling a spot plate, and displaying no amino compound left, wherein the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction is present, and passing through neutral silica gel column to obtain compound 262. Elemental analysis actual measurement: c,91.53; h,5.10; n,3.37.LC-MS: actual measurement value: 827.21 ([ M+H) ]+)。
Preparation of organic electroluminescent device
The molecular structural formula of the materials involved in the following preparation process is shown as follows:
device comparative example 1
The organic electroluminescent device is prepared according to the following steps:
as shown in fig. 1, the substrate layer 1 is transparent glass, and the anode layer 2 (Ag (100 nm)) is washed, that is, sequentially alkali-washed, pure water-washed, dried, and then ultraviolet-ozone-washed to remove organic residues on the surface of the anode layer. On the anode layer 2 after the above washing, HT-1 and P-1 having film thicknesses of 10nm were vapor deposited as hole injection layers 3 by a vacuum vapor deposition apparatus, and the mass ratio of HT-1 and P-1 was 97:3. Next, HT-1 was evaporated to a thickness of 117nm as a hole transport layer 4. Subsequently EB-1 was evaporated to a thickness of 10nm as an electron blocking layer 5. After the evaporation of the electron blocking material is completed, a light emitting layer 6 of the OLED light emitting device is manufactured, and the structure of the light emitting layer comprises BH-1 used by the OLED light emitting layer 6 as a main material, BD-1 as a doping material, the doping material doping ratio is 3% by weight, and the film thickness of the light emitting layer is 20nm. After the light-emitting layer 6 was deposited, HB-1 was further deposited to a thickness of 8nm as a hole blocking layer 7. And (3) continuously evaporating ET-1 and Liq on the hole blocking layer 7, wherein the mass ratio of the ET-1 to the Liq is 1:1. The vacuum deposition film thickness of the material is 30nm, and the layer is an electron transport layer 8. On the electron transport layer 8, a LiF layer having a film thickness of 1nm, which is an electron injection layer 9, was formed by a vacuum vapor deposition apparatus. On the electron injection layer 9, mg having a film thickness of 16nm was produced by a vacuum vapor deposition apparatus: the mass ratio of Mg to Ag in the Ag electrode layer is 1:9, and the Ag electrode layer is used as the cathode layer 10. On the cathode layer 10, 65nm of CP-1 was vacuum-deposited as CPL layer 11.
Device comparative examples 2 to 4
The procedure of device comparative example 1 was conducted except that the organic materials in the hole injection layer and the hole transport layer were replaced with the organic materials shown in table 3, respectively.
Device examples 1 to 18
The procedure of device comparative example 1 was conducted except that the organic materials in the hole injection layer and the hole transport layer were replaced with the organic materials shown in Table 3, respectively.
TABLE 3 Table 3
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Taking example 1 row as an example in the table above, the "P-1:1=3:9710 nm" in the second column table indicates that the hole injection layer uses the compound 1 and the P-type doping material P-1, and the weight ratio of the P-type doping material to the compound 1 is 3:9710nm represents the thickness of the layer; the third column of the tables, "1117nm" indicates that the material used is compound 1 and the layer thickness is 117nm. And so on in other tables.
After the OLED light-emitting device was fabricated as described above, the cathode and anode were connected using a well-known driving circuit, and various properties of the device were measured.
The results of measuring the performance of the devices of examples 1 to 18 and comparative examples 1 to 4 are shown in Table 4.
TABLE 4 Table 4
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Note that: the current efficiency and color coordinates were measured using an IVL (Current-Voltage-Brightness) test system (Freund's scientific instruments Co., ltd.) with a current density of 10mA/cm 2 The method comprises the steps of carrying out a first treatment on the surface of the The life test system is an EAS-62C OLED device life tester of Japanese system technical research company; LT95 refers to the time taken for the device brightness to decay to 95% at a particular brightness; the high temperature lifetime test temperature is 85 ℃, LT80 refers to the time taken for the device brightness to decay to 80% at a particular brightness.
As can be seen from the results of table 4, the arylamine organic compound of the present invention is used as a hole injection and hole transport layer material, and has a higher carrier transport rate, so that the device efficiency and the device lifetime, particularly the device efficiency and the high temperature lifetime, are effectively improved.

Claims (10)

1. An arylamine organic compound is characterized in that the structure of the compound is shown as a general formula (1):
in the general formula 1, R 1 To R 12 Are each independently represented by formula A, a hydrogen atom, a phenyl group, a methyl group, a deuterated tert-butyl group, a tert-butyl group, an adamantyl group, a naphthyl group, wherein R 1 To R 12 At least one of which is represented by formula A;
when R is 1 -R 12 When the compound is represented by phenyl or naphthyl, R 1 -R 12 The connection mode with the benzene ring can be single bond connection or parallel ring connection;
R 0 represented by methyl, ethyl, t-butyl, phenyl, biphenyl, naphthyl, benzofuranyl or benzothienyl;
In formula A, the Ar 1 And Ar is a group 2 Each independently represents a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted 5-30 membered heteroaryl;
said L, L 1 、L 2 Each independently represents a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted 5-30 membered heteroarylene group;
the substituents of the foregoing substituted or unsubstituted groups are each optionally selected from deuterium atoms, methyl, deuterated methyl, ethyl, t-butyl, adamantyl, C6-C30 aryl or 5-30 membered heteroaryl;
the hetero atom in the heteroaryl is selected from one or more of oxygen atom, sulfur atom or nitrogen atom.
2. The aromatic amine-based organic compound according to claim 1, wherein the structure of the organic compound is represented by any one of the general formulae (1-1) to (1-6):
in the general formulae (1-1) to (1-6), R 1 To R 12 Each independently represents a hydrogen atom, phenyl, methyl, deuterated tert-butyl, adamantyl, naphthyl;
when R is 1 -R 12 When the compound is represented by phenyl or naphthyl, R 1 -R 12 The connection mode with the benzene ring can be single bond connection or parallel ring connection;
R 0 represented by methyl, ethyl, t-butyl, phenyl, biphenyl, naphthyl, benzofuranyl or benzothienyl;
The Ar is as follows 1 And Ar is a group 2 Each independently represents a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted 5-30 membered heteroaryl;
the L represents a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted 5-30 membered heteroarylene group;
the substituents of the foregoing substituted or unsubstituted groups are each optionally selected from deuterium atoms, methyl, deuterated methyl, ethyl, t-butyl, adamantyl, C6-C30 aryl or 5-30 membered heteroaryl;
the hetero atom in the heteroaryl is selected from one or more of oxygen atom, sulfur atom or nitrogen atom.
3. The aromatic amine-based organic compound according to claim 2, wherein the structure of the organic compound is represented by any one of the general formulae (1-1) to (1-6);
in the general formulae (1-1) to (1-6), R 1 To R 12 Each independently represents a hydrogen atom, phenyl, methyl, deuterated methyl, tertiary butyl, adamantyl, naphthyl;
when R is 1 -R 12 When the compound is represented by phenyl or naphthyl, R 1 -R 12 The connection mode with the benzene ring can be single bond connection or parallel ring connection;
R 0 represented by methyl, ethyl, t-butyl, phenyl, biphenyl, naphthyl, benzofuranyl or benzothienyl;
the Ar is as follows 1 And Ar is a group 2 Each independently represents one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted piperonyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted indolo-cyclic group;
The L represents one of single bond, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted furyl, substituted or unsubstituted benzofuranyl and substituted or unsubstituted benzothienyl;
the substituent of the above-mentioned substituted or unsubstituted group is selected from one or several of deuterium atom, methyl, deuterated methyl, ethyl, tertiary butyl, adamantyl, phenyl, biphenyl, naphthyl, pyridyl and naphthyridinyl.
4. The aromatic amine-based organic compound according to claim 1, wherein the structure of the organic compound is represented by any one of the general formulae (1 to 7) to (1 to 9):
in the general formulae (1-7) to (1-9), the R 0 、Ar 1 Ar, ar 2 The meaning of (1) is as defined in claim 1;
the L represents one of single bond, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted furyl, substituted or unsubstituted benzofuranyl and substituted or unsubstituted benzothienyl;
the substituents of the foregoing substituted or substituted groups are each optionally selected from one or more of deuterium atom, methyl, deuterated methyl, ethyl, tert-butyl, adamantyl, phenyl, naphthyl, biphenyl.
5. The aromatic amine-based organic compound according to claim 1, wherein the structure of the organic compound is represented by any one of the general formulae (1 to 10) to (1 to 11):
in the general formulae (1-10) to (1-11), the Ar 1 And Ar is a group 2 The meaning of (1) is as defined in claim 1;
the L represents one of single bond, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted furyl, substituted or unsubstituted benzofuranyl and substituted or unsubstituted benzothienyl;
the substituents of the foregoing substituted or substituted groups are each optionally selected from one or more of deuterium atom, methyl, deuterated methyl, ethyl, tert-butyl, adamantyl, phenyl, naphthyl, biphenyl.
6. The aromatic amine-based organic compound according to claim 1, wherein the structure of the organic compound is represented by general formula (1-12):
in the general formula (1-12), the Ar 1 And Ar is a group 2 Each independently represents one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted piperonyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted carbazolyl group, and a substituted or unsubstituted indolo-cyclic group.
The substituents of the foregoing substituted or substituted groups are each optionally selected from one or more of deuterium atom, methyl, deuterated methyl, ethyl, tert-butyl, adamantyl, phenyl, naphthyl, biphenyl.
7. The aromatic amine-based organic compound according to claim 1, wherein the L, L 1 、L 2 Each independently represents a single bond or a structure as shown below:
any one of them.
The Ar is as follows 1 And Ar is a group 2 Each independently represented by the structure shown below:
any one of them.
8. The aromatic amine-based organic compound according to claim 1, wherein the specific structure of the organic compound is any one of the following structures:
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9. an organic electroluminescent device comprising, in order, an anode, a hole transporting region, a light emitting region, an electron transporting region, and a cathode, wherein the hole transporting region comprises the aromatic amine-based organic compound according to any one of claims 1 to 8.
10. The organic electroluminescent device according to claim 9, wherein the hole transport region comprises a hole injection layer, a hole transport layer, and an electron blocking layer, the hole transport layer comprising the aromatic amine compound according to any one of claims 1 to 7.
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