An aromatic organic compound and an organic electroluminescent device comprising the same.

Abstract

This invention relates to an aromatic amine organic compound and an organic electroluminescent device containing the same, belonging to the field of semiconductor materials technology. The structure of the compound provided by this invention is shown in general formula (1): When the hole transport material or electron blocking layer material of the organic electroluminescent device is prepared by using the aromatic amine compound of this invention, the device voltage can be reduced and the device life can be extended at the same time, especially the device high temperature life is significantly improved.

Description

Technical Field

[0001] This invention relates to the field of semiconductor technology, and more particularly to an aromatic amine organic compound and an organic electroluminescent device containing the same. Background Technology

[0002] Organic light-emitting diode (OLED) technology can be used to manufacture new display products and new lighting products, and it is expected to replace existing liquid crystal displays and fluorescent lighting, with a very wide range of applications. OLED light-emitting devices have a sandwich-like structure, including electrode material layers and organic functional materials sandwiched between different electrode material layers. Various organic functional materials are stacked together according to their intended use to form the OLED light-emitting device. As a current-carrying device, when a voltage is applied to the two electrodes of the OLED light-emitting device, and the positive and negative charges in the organic functional material layers are acted upon by an electric field, the positive and negative charges recombine in the light-emitting layer, thus generating OLED electroluminescence.

[0003] Currently, OLED display technology has been applied in smartphones, tablets, and other fields, and will further expand into large-screen applications such as televisions. However, compared with the requirements of actual product applications, the luminous efficiency, lifespan, and other performance characteristics of OLED devices still need further improvement. Research on improving the performance of OLED light-emitting devices includes: reducing the driving voltage of the device, increasing the luminous efficiency of the device, and increasing the lifespan of the device. To continuously improve the performance of OLED devices, it is necessary not only to innovate in OLED device structure and manufacturing processes, but also to continuously research and innovate OLED optoelectronic functional materials to create functional materials for higher-performance OLEDs.

[0004] Blue organic light-emitting diodes (OLEDs) have always been a weak point in the development of full-color OLEDs. To date, the efficiency and lifespan of blue light-emitting devices have been difficult to improve comprehensively. Therefore, improving the performance of these devices remains a crucial issue and challenge in this field. Currently, most blue light-emitting substrates used in the market are electron-biased. At low current densities, preferential hole injection alleviates the pressure on the hole transport side to some extent. However, as the current density increases, the amount of electron injection increases, causing the recombination region to shift towards the hole side, increasing the pressure on the hole side. Currently, the exciton stability of the hole-side materials still cannot meet the requirements, and the hole mobility at high current densities needs to be improved to ensure carrier balance in the light-emitting layer and prevent the recombination region from shifting towards the hole transport side due to insufficient holes, leading to reduced device efficiency and shorter lifespan. Summary of the Invention

[0005] In view of the above-mentioned problems in the prior art, the applicant of this invention provides an aromatic amine organic compound and an organic electroluminescent device containing the same. The compound of this invention can effectively improve the lifespan and efficiency of the electroluminescent device.

[0006] The technical solution of the present invention is as follows: an aromatic amine organic compound, the structure of which is shown in general formula (1):

[0007]

[0008] In general formula (1), L1 and L2 are respectively independently represented as single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene or substituted or unsubstituted biphenylene;

[0009] R1 and R2 are independently represented as substituted or unsubstituted C5-C, respectively. 30 Aryl, substituted or unsubstituted 5-30 heteroaryl groups;

[0010] The R4 is represented as a hydrogen atom, a deuterium atom, or the structure shown in general formula (2);

[0011] R3 represents a hydrogen atom, a deuterium atom, a phenyl group, or the structure shown in general formula (2), and R3 and R4 are not simultaneously hydrogen atoms and deuterium atoms;

[0012] Z1-Z5 are each independently represented as a hydrogen atom or a deuterium atom;

[0013] The n represents the number 0, 1, 2 or 3;

[0014] And when R3 represents phenyl, n represents 0;

[0015] And when R3 or R4 is represented as the structure shown in general formula (2), n is not represented as 0;

[0016] In general formula (2), X represents an oxygen atom or a sulfur atom;

[0017] The R6-R 13 Represented independently as hydrogen atom, deuterium atom, and carbon atom. 1- C 10 Alkyl, substituted or unsubstituted C5-C 30 Aryl, substituted or unsubstituted 5-30 heteroaryl groups, and R6-R 13 Two adjacent groups can bond together to form a ring;

[0018] The substituents of the substituted or unsubstituted groups are optionally selected from deuterium atoms, C1-C1 atoms, and C2-C3 atoms. 10 Alkyl, C5-C 30 Aryl or 5-30 heteroaryl compounds.

[0019] In a preferred embodiment, the structure of the organic compound is shown in general formula (1-2) or general formula (1-3):

[0020]

[0021] In general formulas (1-2) and (1-3), L1 and L2 are independently represented as single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, or substituted or unsubstituted biphenylene, respectively.

[0022] R1 and R2 are independently represented as substituted or unsubstituted C5-C, respectively. 30 Aryl, substituted or unsubstituted 5-30 heteroaryl groups;

[0023] The R4 atoms are independently represented by hydrogen atoms and deuterium atoms, respectively.

[0024] R3 represents hydrogen atom and deuterium atom.

[0025] The n is represented by the number 1, 2, or 3;

[0026] X represents an oxygen atom or a sulfur atom;

[0027] The R7-R 13 Represented independently as hydrogen atom, deuterium atom, and carbon atom. 1- C 10 Alkyl, substituted or unsubstituted C5-C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl, and two adjacent groups can bond together to form a ring;

[0028] The substituents of the substituted or unsubstituted groups are optionally selected from deuterium atoms, C1-C1 atoms, and C2-C3 atoms. 10 Alkyl, C5-C 30 Aryl or 5-30 heteroaryl compounds.

[0029] In a preferred embodiment, the structure of the organic compound is shown in general formula (1-4) or general formula (1-5):

[0030]

[0031] In general formulas (1-4) and (1-5), L1 and L2 are independently represented as single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, or substituted or unsubstituted biphenylene, respectively.

[0032] R1 and R2 are independently represented as substituted or unsubstituted C5-C, respectively. 30 Aryl, substituted or unsubstituted 5-30 heteroaryl groups;

[0033] The R4 atoms are independently represented by hydrogen atoms and deuterium atoms, respectively.

[0034] R3 represents hydrogen atom and deuterium atom.

[0035] X represents an oxygen atom or a sulfur atom;

[0036] The R7-R 13 Represented independently as hydrogen atom, deuterium atom, and carbon atom. 1- C 10 Alkyl, substituted or unsubstituted C5-C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl, and two adjacent groups can bond together to form a ring;

[0037] The substituents of the substituted or unsubstituted groups are optionally selected from deuterium atoms, C1-C1 atoms, and C2-C3 atoms. 10 Alkyl, C5-C 30 Aryl or 5-30 heteroaryl compounds.

[0038] In a preferred embodiment, the structure of the organic compound is shown in general formula (1-6):

[0039]

[0040] In general formulas (1-6), L1 and L2 are independently represented as single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, or substituted or unsubstituted biphenylene, respectively.

[0041] R1 and R2 are independently represented as substituted or unsubstituted C5-C, respectively. 30 Aryl, substituted or unsubstituted 5-30 heteroaryl groups;

[0042] The substituents of the substituted or unsubstituted groups are optionally selected from deuterium atoms, C1-C1 atoms, and C2-C3 atoms. 10 Alkyl, C5-C 30 Aryl or 5-30 heteroaryl compounds.

[0043] In a preferred embodiment, the structure of the organic compound is shown in general formula (1-7) or general formula (1-8):

[0044]

[0045] In general formulas (1-7) and (1-8), L1 and L2 are independently represented as single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, or substituted or unsubstituted biphenylene, respectively.

[0046] R2 represents substituted or unsubstituted C5-C. 30 Aryl, substituted or unsubstituted 5-30 heteroaryl groups;

[0047] X1 represents oxygen atom, sulfur atom, and NR. 16 or C(R)14 R 15 );

[0048] The R 14 R 15 Represented as methyl or phenyl, R 16 Indicated as substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl;

[0049] Z represents a carbon atom or C-R0;

[0050] R0 represents hydrogen atom, deuterium atom, and C atom. 1- C 10 Alkyl, substituted or unsubstituted C5-C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl, and two adjacent R0s can bond to each other to form a ring;

[0051] The substituents of the substituted or unsubstituted groups are optionally selected from deuterium atoms, C1-C1 atoms, and C2-C3 atoms. 10 Alkyl, C5-C 30 Aryl or 5-30 heteroaryl compounds.

[0052] In a preferred embodiment, the structure of the organic compound is shown in general formulas (1-9), (1-10), (1-11), (1-12), or (1-13):

[0053] In general formulas (1-9), (1-10), (1-11), (1-12), and (1-13), L1 and L2 are independently represented as single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, or substituted or unsubstituted biphenylene, respectively.

[0054] R2 represents substituted or unsubstituted C5-C. 30 Aryl, substituted or unsubstituted 5-30 heteroaryl groups;

[0055] R represents a hydrogen atom or a phenyl group, and the connection of R is either a single bond or a cyclic ring;

[0056] The substituents of the substituted or unsubstituted groups are optionally selected from deuterium atoms, C1-C1 atoms, and C2-C3 atoms. 10 Alkyl, C5-C 30 Aryl or 5-30 heteroaryl compounds.

[0057] In a preferred embodiment, the structure of the organic compound is shown in general formula (1-16):

[0058]

[0059] In general formula (1-16), L1 and L2 are independently represented as single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, or substituted or unsubstituted biphenylene, respectively.

[0060] R2 represents substituted or unsubstituted C5-C. 30 Aryl, substituted or unsubstituted 5-30 heteroaryl groups;

[0061] X1 represents oxygen atom, sulfur atom, and NR. 16 or C(R) 14 R 15 );

[0062] The R 14 R 15 Represented as methyl or phenyl, R 16 Indicated as substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl;

[0063] Z represents a carbon atom or C-R0;

[0064] R0 represents hydrogen atom, deuterium atom, and C atom. 1- C 10 Alkyl, substituted or unsubstituted C5-C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl, and two adjacent R0s can bond to each other to form a ring;

[0065] The substituents of the substituted or unsubstituted groups are optionally selected from deuterium atoms, C1-C1 atoms, and C2-C3 atoms. 10 Alkyl, C5-C 30 Aryl or 5-30 heteroaryl compounds.

[0066] In a preferred embodiment, the structure of the organic compound is shown in general formulas (1-14) and (1-15):

[0067]

[0068] In general formulas (1-14) and (1-15), L2 represents a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted biphenylene.

[0069] R2 represents substituted or unsubstituted C5-C. 30 Aryl, substituted or unsubstituted 5-30 heteroaryl groups;

[0070] R represents a hydrogen atom or a phenyl group, and the connection of R is either a single bond or a cyclic ring;

[0071] The substituents of the substituted or unsubstituted groups are optionally selected from deuterium atoms, C1-C1 atoms, and C2-C3 atoms. 10 Alkyl, C5-C 30Aryl or 5-30 heteroaryl compounds.

[0072] In a preferred embodiment, R1 and R2 are respectively independently represented as substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted indene, substituted or unsubstituted piperonyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted diphenylfluorenyl, and substituted or unsubstituted carbazoyl.

[0073] The R6-R 13 Each can be represented independently as a hydrogen atom, deuterium atom, methyl, ethyl, tert-butyl, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted indene, substituted or unsubstituted piperonyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted carbazoyl.

[0074] In a preferred embodiment, RO represents a hydrogen atom, a deuterium atom, methyl, ethyl, tert-butyl, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted indene, substituted or unsubstituted piperonyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted diphenylfluorenyl, or substituted or unsubstituted carbazoyl.

[0075] In a preferred embodiment, the substituent of the substituted or unsubstituted group is selected from deuterium, methyl, ethyl, tert-butyl, adamantyl, phenyl, naphthyl, biphenyl, furanyl, thiophene, benzofuranyl, benzothiophene, dibenzofuranyl, or dibenzothiophene.

[0076] An aromatic amine organic compound having the structure shown in general formula (A), general formula (B), general formula (C) or general formula (D):

[0077]

[0078] In general formulas (A), (B), (C), and (D), X is represented as O or S;

[0079] The L a Indicated as substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, or substituted or unsubstituted diphenylene;

[0080] The L b L c L d L g L h Represented as a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, or substituted or unsubstituted diphenylene;

[0081] The L e L f Represented as phenylene or naphthylene;

[0082] The R a R b R c R e R f Each can be represented independently as substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted diphenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiopheneyl.

[0083] The R d Represented as phenyl or naphthyl, and when L d Represented as phenylene, R c L f When represented as naphthyl, R d It can be represented as a hydrogen atom;

[0084] The substituents of the substituted or unsubstituted groups may be selected from deuterium, phenyl, naphthyl, or diphenyl.

[0085] In a preferred embodiment, the structure of the organic compound is shown in general formula (A-1) or general formula (D-1):

[0086]

[0087] In general formulas (A-1) and (D-1), X is represented as O or S;

[0088] The L b L g L h Represented as a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, or substituted or unsubstituted diphenylene;

[0089] The R a R e R f Each can be represented independently as substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted diphenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiopheneyl.

[0090] The substituents of the substituted or unsubstituted groups may be selected from deuterium, phenyl, naphthyl, or diphenyl.

[0091] In a preferred embodiment, the specific structure of the compound is any one of the following structures:

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104] The present invention also provides an organic electroluminescent device, comprising a cathode, an anode, and an organic functional layer, wherein the organic functional layer is located between the cathode and the anode, and at least one organic functional layer of the organic electroluminescent device contains the aforementioned aromatic amine organic compound.

[0105] In a preferred embodiment, the organic functional layer includes a hole transport region, a light-emitting region, and an electron transport region, wherein the hole transport region contains the aromatic amine compound.

[0106] In a preferred embodiment, the hole transport region includes a hole injection layer, a hole transport layer, and an electron blocking layer, wherein the hole transport layer and / or the electron blocking layer contains the aromatic amine compound.

[0107] In a preferred embodiment, the hole transport region includes a hole injection layer, a hole transport layer, and an electron blocking layer, wherein the electron blocking layer contains the aromatic amine compound.

[0108] In a preferred embodiment, the hole transport region includes a hole injection layer, a hole transport layer, and an electron blocking layer, wherein the hole transport layer contains the aromatic amine compound.

[0109] Compared with the prior art, the beneficial technical effects of the present invention are as follows:

[0110] When the aromatic amine compounds of the present invention replace dibenzofuran on naphthalene, the compounds of the present invention will have a better exciton blocking ability, so that the excitons are better localized in the luminescent region, ensuring a high exciton concentration in the luminescent region, improving the utilization rate of excitons, and thus improving the luminescence efficiency.

[0111] When the aromatic amine compounds of this invention replace the phenyl group on naphthalene, the compounds of this invention exhibit superior hole mobility at high current densities. When applied to devices, they improve device efficiency while also providing excellent device lifespan, especially significantly enhancing high-temperature lifespan. Attached Figure Description

[0112] Figure 1 This is a schematic diagram of the structure of an OLED device in which the materials listed in this invention are applied;

[0113] Among them, 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light-emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, 10 is a cathode layer, and 11 is a capping layer.

[0114] Figure 2 This is the 1H NMR spectrum of compound 139;

[0115] Figure 3 This is the 1H NMR spectrum of compound 143;

[0116] Figure 4 This is the 1H NMR spectrum of compound 148;

[0117] Figure 5 This is the 1H NMR spectrum of compound 359. Detailed Implementation

[0118] The technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. The following description of at least one exemplary embodiment is merely illustrative and is in no way intended to limit the present invention or its application or use. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention.

[0119] In this invention, when a layer or element is referred to as being "above" another layer or substrate, the layer or element may be located directly above the other layer or substrate, or there may be intermediate layers. Furthermore, it will be understood that when a layer is referred to as being "between" two layers, the layer may be the only layer between the two layers, or there may be one or more intermediate layers. The same reference numerals throughout the drawings denote the same elements.

[0120] In this invention, the terms "upper," "lower," "top," and "bottom," used to describe electrodes, organic electroluminescent devices, and other structures, indicate orientation only in a specific state and do not imply that the structure can only exist in that orientation. Conversely, if the structure can be repositioned, such as by inverting it, the orientation of the structure changes accordingly. Specifically, in this invention, the "bottom" or "lower" side of the electrode refers to the side of the electrode closer to the substrate during fabrication, while the opposite side farther from the substrate is the "top" or "upper" side.

[0121] In this specification, the term "substitution" means that one or more hydrogen atoms on a specified atom or group are replaced by a specified group, provided that the normal valence of the specified atom is not exceeded under the existing conditions.

[0122] In this specification, hole characteristics refer to the characteristics that allow holes formed in the anode to be easily injected into and transported in the light-emitting layer when an electric field is applied, due to conductivity characteristics at the highest occupied molecular orbital (HOMO) level.

[0123] In this specification, electronic characteristics refer to the characteristics that allow electrons formed in the cathode to be readily injected into and transported in the light-emitting layer when an electric field is applied, and which are attributed to conductivity characteristics based on the lowest unoccupied molecular orbital (LUMO) level.

[0124] The organic electroluminescent device of the present invention can be a bottom-emitting organic electroluminescent device, a top-emitting organic electroluminescent device, or a multilayer organic electroluminescent device, and there is no specific limitation thereto.

[0125] In the organic electroluminescent device of this invention, any substrate commonly used in organic electroluminescent devices can be used. Examples include transparent substrates, such as glass or transparent plastic substrates; opaque substrates, such as silicon substrates; and flexible polyimide (PI) film substrates. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance. Their application varies depending on their properties. In this invention, a transparent substrate is preferred. There are no particular limitations on the thickness of the substrate.

[0126] anode

[0127] Preferably, the anode can be formed on the substrate. In this invention, the anode and cathode are opposite each other. The anode can be made of a conductor with a high work function to facilitate hole injection, and can be, for example, a metal such as nickel, platinum, copper, zinc, silver or alloys thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); a combination of metal and metal oxide, such as ZnO and Al or ITO and Ag; a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene), and polyaniline, but is not limited thereto. The thickness of the anode depends on the material used, typically 50-500 nm, preferably 70-300 nm, and more preferably 100-200 nm. In this invention, a combination of metal and metal oxide, ITO and Ag, is preferred.

[0128] cathode

[0129] The cathode can be made of a conductor with a low work function to facilitate electron injection, and can be, for example, a metal or alloy thereof, such as magnesium, calcium, sodium, potassium, titanium, indium, aluminum, silver, tin, and combinations thereof; multilayer materials, such as LiF / Al, Li2O / Al, and BaF2 / Ca, but not limited thereto. The thickness of the cathode depends on the material used, typically 10-50 nm, preferably 15-20 nm.

[0130] Light-emitting area

[0131] In this invention, the light-emitting region can be disposed between the anode and the cathode, and can include at least one host material and at least one guest material. Both the host and guest materials of the light-emitting region in the organic electroluminescent device of this invention can be light-emitting layer materials known in the prior art for organic electroluminescent devices. The host material can be, for example, a thiazole derivative, a benzimidazole derivative, a polydialkylfluorene derivative, or 4,4'-bis(9-carbazolyl)biphenyl (CBP). The host material can be a compound containing anthracene groups. The guest material can be, for example, a quinacridone, coumarin, rubrene, perylene and its derivatives, benzopyran derivatives, rhodamine derivatives, or aminostyrene derivatives.

[0132] In a preferred embodiment of the present invention, the luminescent region contains one or two host material compounds.

[0133] In a preferred embodiment of the present invention, the host material of the luminescent region is selected from one or more of the following compounds BH-1-BH-11:

[0134]

[0135] In this invention, the luminescent region may contain phosphorescent or fluorescent guest materials to improve the fluorescence or phosphorescence properties of the organic electroluminescent device. Specific examples of phosphorescent guest materials include metal complexes of iridium, platinum, etc., while those commonly used in the art can be used for fluorescent guest materials. In a preferred embodiment of this invention, the guest material used in the luminescent film layer is selected from one of the following compounds: BD-1 to BD-10.

[0136]

[0137] In the light-emitting region of the present invention, the ratio of the host material to the guest material is 99:1-70:30, preferably 99:1-85:15 and more preferably 97:3-87:13, based on mass.

[0138] The thickness of the light-emitting region can be 10-50 nm, preferably 15-30 nm, but the thickness is not limited to this range.

[0139] Hole transport region

[0140] 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.

[0141] Hole injection layer

[0142] The hole injection material used in the hole injection layer (also known as the anode interface buffer layer) is a material capable of fully accepting holes from the anode at low voltages, 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 invention, the hole injection layer is a mixed film layer of a host organic material and a p-type dopant. For holes to be smoothly injected from the anode into the organic film layer, the HOMO energy level of the host organic material must possess certain characteristics with the p-type dopant to facilitate charge transfer states between the host and dopant materials, achieving ohmic contact between the hole injection layer and the anode, thereby achieving efficient hole injection from the electrode to the hole injection layer. This characteristic is summarized as follows: the difference between the HOMO energy level of the host material and the LUMO energy level of the p-type dopant is ≤0.4 eV. Therefore, for hole-type host materials with different HOMO energy levels, different p-type dopant materials need to be selected to match them in order to achieve ohmic contact at the interface and improve the hole injection effect.

[0143] Preferably, specific examples of the host organic material include: metalloporphyrins, oligothiophenes, aromatic amine organic materials, hexanitrile hexaazabenzanphenanthrene, quinacridone organic materials, perylene organic materials, anthraquinones, polyanilines, and polythiophene conductive polymers; but are not limited thereto. Preferably, the host organic material is an aromatic amine organic compound.

[0144] Preferably, the p-type doped material is a charge-conducting compound selected from quinone derivatives or metal oxides, such as tungsten oxide and molybdenum oxide, but not limited thereto.

[0145] In a preferred embodiment of the present invention, the p-type doped material used is selected from any one of the following compounds HI1 to HI8:

[0146]

[0147] In one embodiment of the present invention, the ratio of the host organic material to the P-type doped material is 99:1-95:5, preferably 99:1-97:3, based on mass.

[0148] In a preferred embodiment of the present invention, the hole injection layer is a mixed film layer of aromatic amine compound and P-type doped material, wherein the aromatic amine compound is an aromatic amine compound of general formula (1).

[0149] The thickness of the hole injection layer of the present invention can be 5-20 nm, preferably 8-15 nm, but the thickness is not limited to this range.

[0150] Hole transport layer

[0151] In the organic electroluminescent device of the present invention, a hole transport layer may be disposed above a hole injection layer. The hole transport material is a suitable material with high hole mobility, capable of accepting holes from the anode or hole injection layer and transporting the holes to the light-emitting layer. Specific examples include, but are not limited to, aromatic amine organic materials, conductive polymers, block copolymers having both conjugated and non-conjugated portions. In a preferred embodiment, the hole transport layer comprises an aromatic amine organic compound of the same general formula (1) as the hole injection layer.

[0152] The thickness of the hole transport layer of the present invention can be 80, 100 or 200 nm, preferably 100-150 nm, but the thickness is not limited to this range.

[0153] Electron blocking layer

[0154] 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 in contact with the light-emitting layer. By disposing of the electron blocking layer in contact with the light-emitting layer, hole transfer at the interface between the light-emitting layer and the hole transport layer can be precisely controlled. In one embodiment of the present invention, the electron blocking layer material is selected from aromatic amine compounds of general formula (1). The thickness of the electron blocking layer may be 5-20 nm, preferably 8-15 nm, but is not limited to this range.

[0155] Electronic transmission area

[0156] In the organic electroluminescent device of the present invention, the electron transport region is disposed between the light-emitting region and the cathode, and includes, but is not limited to, a hole blocking layer, an electron transport layer and an electron injection layer.

[0157] Electron injection layer

[0158] An electron injection layer may be disposed between the electron transport layer and the cathode. The electron injection layer material is typically preferably a material with a low work function, allowing electrons to be easily injected into the organic functional material layer. Preferably, the electron injection layer material is an N-type metal. As the electron injection layer material for the organic electroluminescent device of the present invention, electron injection layer materials known in the art for organic electroluminescent devices can be used, such as lithium; lithium salts, such as lithium 8-hydroxyquinoline, lithium fluoride, lithium carbonate, or lithium azide; or cesium salts, such as cesium fluoride, cesium carbonate, or cesium azide. The thickness of the electron injection layer of the present invention may be 0.1-5 nm, preferably 0.5-3 nm, and more preferably 0.8-1.5 nm, but the thickness is not limited to this range.

[0159] Electron transport layer

[0160] An electron transport layer may be disposed above the light-emitting film layer or (if present) a hole-blocking layer. The electron transport layer material is one that readily receives electrons from the cathode and transfers the received electrons to the light-emitting layer. A material with high electron mobility is preferred. As the electron transport layer of the organic electroluminescent device of the present invention, electron transport layer materials known in the prior art for organic electroluminescent devices can be used, such as metal complexes of hydroxyquinoline derivatives represented by 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-(naphth-2-yl)-1,3,5-triazine (CAS No.: 1459162-51-6), imidazole derivatives such as 2-(4-(9,10-bis(naphth-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole (CAS No.: 561064-11-7, commonly known as LG201), oxadiazole derivatives, etc.

[0161] In a preferred organic electroluminescent device of the present invention, the electron transport layer comprises a compound represented by general formula (3):

[0162]

[0163] In general formula (3), Ar1, Ar2, Ar3, and Ar4 are independently selected from substituted or unsubstituted C6-C. 30 Aryl, substituted or unsubstituted C3-C containing one or more heteroatoms 30 One of the heterocyclic groups;

[0164] L3 represents C6-C with a single bond, substitution, or no substitution. 30 aryl, substituted or unsubstituted C3-C containing one or more heteroatoms 30 One of the sub-heterocyclic groups;

[0165] X1, X2, X3, X4, X5, and X6 independently represent N or CH, at least one of X1, X2, and X3 represents N, and at least one of X4, X5, and X6 represents N;

[0166] The heteroatoms are selected from N, O, or S;

[0167] The substituents used for the substituent groups are one or more of the following: deuterium, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, or pyrimidinyl.

[0168] In a preferred embodiment, Ar1, Ar2, Ar3, and Ar4 are independently represented as one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted dibenzothiophene, or substituted or unsubstituted quinolinyl.

[0169] The L3 is represented as a single bond, phenylene, biphenylene, or naphthylene;

[0170] The substituents used for the substituent groups are one or two of the following: deuterium, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, and pyrimidinyl.

[0171] In a more preferred embodiment of the invention, the electron transport layer comprises a compound selected from the following:

[0172]

[0173] In a preferred embodiment of the invention, in addition to the compound of general formula (3), the electron transport layer also includes other compounds conventionally used for electron transport layers, such as Alq3, LiQ, preferably LiQ. In a more preferred embodiment of the invention, the electron transport layer consists of one of the compounds of general formula (3) and another of the compounds conventionally used for electron transport layers (preferably LiQ).

[0174] The hole injection and transport rates of the hole transport region containing the aromatic amine compound of the present invention can be well matched with the electron injection and transport rates. Preferably, the hole injection and transport rates of the hole transport region containing the aromatic amine compound of the present invention can be better matched with the electron injection and transport rates of the electron transport region containing the compound of general formula (3).

[0175] Therefore, in a particular embodiment of the present invention, using an electron transport region containing one or more compounds of general formula (3) or composed thereof, in combination with a hole transport region containing an aromatic amine compound of the present invention, achieves relatively better technical results.

[0176] The thickness of the electron transport layer of the present invention can be 10-80 nm, preferably 20-60 nm, and more preferably 25-45 nm, but the thickness is not limited to this range.

[0177] Cover layer

[0178] To improve the light extraction efficiency of organic electroluminescent devices, a light extraction layer (CPL layer, also known as a capping layer) can be added to the cathode of the device. According to the principles of optical absorption and refraction, the CPL capping layer material should have a higher refractive index and a lower absorption coefficient. Any material known in the art can be used as the CPL layer material, such as Alq3 or N4,N4'-diphenyl-N4,N4'-di(9-phenyl-3-carbazolyl)biphenyl-4,4'-diamine. The thickness of the CPL capping layer is typically 5-300 nm, preferably 20-100 nm, and more preferably 40-80 nm.

[0179] The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure preventing external 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 or metal can; or a thin film covering the entire surface of the organic layer.

[0180] The organic electroluminescent device according to an embodiment of the present invention is described below.

[0181] In the accompanying drawings, the thicknesses of layers, films, substrates, regions, etc., are enlarged for clarity. Throughout the specification, the same reference numerals denote the same elements. It should be understood that when an element such as a layer, film, region, or substrate is referred to as "on" another element, it may be directly on the other element or there may be intercalating elements. In contrast, when an element is referred to as "directly on" another element, there are no intercalating elements.

[0182] This invention also relates to a method for fabricating an organic electroluminescent device, comprising 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 can be used, but are not limited thereto. In this invention, vacuum evaporation is preferably used to form the various layers. Those skilled in the art can conventionally select the various process conditions in the vacuum evaporation method according to actual needs.

[0183] In addition, it should be noted that the materials used to form each layer described in this invention can be used as a single layer by forming a film on their own, or they can be used as a single layer by mixing with other materials to form a film. They can also be a stacked structure between layers that are formed on their own, a stacked structure between layers that are formed by mixing, or a stacked structure between layers that are formed on their own and layers that are formed by mixing.

[0184] Preparation Examples

[0185] Synthesis of intermediate C-1:

[0186]

[0187] In a three-necked flask under nitrogen protection, 10 mmol of starting material A-1 and 12 mmol of starting material B-1 were added and dissolved in tetrahydrofuran (THF). Then, 0.1 mmol of Pd(PPh3)4 and 15 mL of 3 mol / L K2CO3 aqueous solution were added. The mixture was heated to reflux for 8 hours under nitrogen protection. A sample was spotted onto a TLC plate to confirm complete reaction. After cooling to room temperature, the reaction mixture was filtered through a diatomaceous earth filter, washed with chloroform, and the resulting filtrate was evaporated under vacuum. The residue was purified by column chromatography on silica gel using hexane / toluene as eluent to give intermediate C-1. LC-MS: Measured value: 373.26 ([M+H]+), theoretical value: 372.01.

[0188] Intermediate C-2 was prepared using a method similar to that used in the synthesis of intermediate C-1, as shown in Table 1 below:

[0189] Table 1

[0190]

[0191] Synthesis of intermediate E-1:

[0192]

[0193] In a three-necked flask under nitrogen protection, 28 mmol of intermediate C-1 and 32 mmol of starting material D-1 were added and dissolved in tetrahydrofuran (THF). Then, 0.1 mmol of Pd(PPh3)4 and 15 mL of 3 mol / L K2CO3 aqueous solution were added. The mixture was heated to reflux for 12 hours under nitrogen protection. A sample was spotted onto a TLC plate to confirm complete reaction. After cooling to room temperature, the reaction mixture was filtered through a diatomaceous earth filter, washed with chloroform, and the resulting filtrate was evaporated under vacuum. The residue was purified by column chromatography on silica gel using hexane / toluene as eluent to give intermediate E-1. LC-MS: Measured value: 405.19 ([M+H]+), theoretical value: 404.10.

[0194] Intermediate E was prepared using a method similar to that used in the synthesis of intermediate E-1, as shown in Table 2 below:

[0195] Table 2

[0196]

[0197]

[0198] Example 1: Synthesis of Compound 1:

[0199]

[0200] In a three-necked flask, under nitrogen protection, add 0.011 mol of intermediate E-1, 0.012 mol of raw material F-1, and 150 mL of toluene, and stir to mix. Then add 5 × 10⁻⁶ mL of toluene. -5 mol Pd2(dba)3, 5×10 -5 0.03 mol of tri-tert-butylphosphine and 0.03 mol of sodium tert-butoxide were heated to 108 °C and refluxed for 20 hours. TLC sampling showed no remaining intermediate E-1, indicating complete reaction. The mixture was allowed to cool naturally to room temperature, filtered, and the filtrate was rotary evaporated until no fraction remained. The filtrate was then passed through a neutral silica gel column to give compound 1. Elemental analysis of the structure (molecular formula C...) 52 H 35 NO): Theoretical values: C, 90.54; H, 5.11; N, 2.03; Measured values: C, 90.52; H, 5.10; N, 2.05. LC-MS: Measured value: 690.35 ([M+H]) + ); Precision quality: 689.27.

[0201] The following compounds were prepared using the same method as in Example 1, and the raw materials are shown in Table 3 below:

[0202] Table 3

[0203]

[0204]

[0205]

[0206] Example 2: Synthesis of Compound 138

[0207]

[0208] (1) In a three-necked flask, under nitrogen protection, add 0.01 mol of raw material G-1, 0.012 mol of raw material H, and 150 ml of toluene and stir to mix. Then add 5 × 10⁻⁶ ml of toluene. -5 mol Pd2(dba) 3 5×10 -5 0.03 mol of tri-tert-butylphosphine and 0.03 mol of sodium tert-butoxide were heated to 105 °C and refluxed for 16 hours. A sample was taken and spotted onto a TLC plate, showing no remaining amine compounds, indicating that the reaction was complete. The mixture was allowed to cool naturally to room temperature, filtered, and the filtrate was rotary evaporated until no fraction remained. The filtrate was then passed through a neutral silica gel column to obtain intermediate P-1.

[0209] (2) In a three-necked flask, under nitrogen protection, add 0.01 mol of intermediate P-1, 0.012 mol of raw material J-1, and 150 mL of toluene and stir to mix. Then add 5 × 10⁻⁶ mol of toluene. -5mol Pd2(dba) 3 5×10 -5 0.03 mol of tri-tert-butylphosphine and 0.03 mol of sodium tert-butoxide were heated to 105 °C and refluxed for 24 hours. A TLC sample was taken, showing no remaining amine compounds, indicating complete reaction. The mixture was allowed to cool naturally to room temperature, filtered, and the filtrate was rotary evaporated until no fraction remained. The filtrate was then passed through a neutral silica gel column to give compound 138. Elemental analysis of the structure (molecular formula C138) is required. 50 H 39 N): Test values: C, 91.89; H, 6.02; N, 2.11. LC-MS: Measured value: 654.17 ([M+H]+).

[0210] The following compounds were prepared using a method similar to that in Example 2, with the same starting material H. Other starting materials G, intermediate P, and starting material J are shown in Table 4 below.

[0211] Table 4

[0212]

[0213]

[0214]

[0215] Example 3: Synthesis of Compound 168

[0216] Step (1)

[0217] Step (2)

[0218] Step (3)

[0219] (1) Under a nitrogen atmosphere, 0.06 mol of raw material K-1 was added to a three-necked flask and dissolved in a mixed solvent (300 ml toluene, 90 ml H2O). The mixture was stirred under nitrogen for 1 hour, and then 0.05 mol of raw material L-1, 0.1 mol of K2CO3, and 0.005 mol of Pd(PPh3)4 were slowly added. The mixture was heated to 90 °C and reacted for 8 hours. The reaction was observed using thin-layer chromatography (TLC) until it was complete. After naturally cooling to room temperature, water was added to the reaction system for extraction, and the mixture was separated. The organic phase was then rotary evaporated under reduced pressure until no fraction was obtained. The obtained substance was purified by silica gel column chromatography to obtain intermediate Q-1.

[0220] (2) Under a nitrogen atmosphere, 0.06 mol of intermediate Q-1 was added to a three-necked flask and dissolved in a mixed solvent (300 mL toluene, 90 mL H2O). The mixture was stirred under nitrogen for 1 hour, and then 0.05 mol of starting material M-1, 0.1 mol of K2CO3, and 0.005 mol of Pd(PPh3)4 were slowly added. The mixture was heated to 90 °C and reacted for 8 hours. The reaction was observed using thin-layer chromatography (TLC) until complete. After naturally cooling to room temperature, water was added to the reaction system for extraction. The mixture was separated, and the organic phase was rotary evaporated under reduced pressure until no fraction was obtained. The obtained substance was purified by silica gel column chromatography to obtain intermediate R-1.

[0221] (3) In a three-necked flask, under nitrogen protection, add 0.01 mol of intermediate P-1, 0.012 mol of intermediate R-1, and 150 mL of toluene, stir and mix, then add 5 × 10⁻⁶ mL of toluene. -5 mol Pd2(dba)3, 5×10 -5 0.03 mol of tri-tert-butylphosphine and 0.03 mol of sodium tert-butoxide were heated to 105 °C and refluxed for 24 hours. A TLC sample was taken, showing no remaining amine compounds, indicating a complete reaction. The mixture was allowed to cool naturally to room temperature, filtered, and the filtrate was rotary evaporated until no fraction remained. The filtrate was then passed through a neutral silica gel column to give compound 168. Elemental analysis of the structure (molecular formula C168) is required. 59 H 43 N): Test values: C, 92.55; H, 5.63; N, 1.83. LC-MS: Measured value: 766.22 ([M+H]+).

[0222] The following compounds were prepared using a method similar to that in Example 3, as shown in the following reaction equations:

[0223] Synthesis of compound 240:

[0224]

[0225] Synthesis of compound 248:

[0226]

[0227] Synthesis of compound 268:

[0228]

[0229]

[0230] Table 5

[0231] Compound structure and numbering <![CDATA[Test results LC-MS ([M+H] + )]]> Compound 240 The measured value was 802.19; elemental analysis measured values: C, 92.81; H, 5.42; N, 1.78. Compound 248 The measured value was 739.35; elemental analysis measured values: C, 91.05; H, 5.19; N, 3.74. Compound 268 The measured value was 756.39; elemental analysis measured values: C, 92.15; H, 6.03; N, 1.81.

[0232] The technical effects of applying the compounds of the present invention to electron blocking layers are illustrated below through device comparative examples 1-6, 11-13 and device examples 1-22.

[0233] Device Comparison Example 1

[0234] The specific preparation process is as follows:

[0235] like Figure 1 As shown, substrate layer 1 is transparent glass. Anode layer 2 (Ag (100nm)) is washed sequentially with alkaline washing, pure water washing, drying, and then ultraviolet-ozone washing to remove organic residues from the surface of the anode layer. After the above washing, a hole injection layer 3 (HT1 and HI1 with a mass ratio of 97:3) is deposited on anode layer 2 using a vacuum evaporation apparatus, with a thickness of 10nm. Next, a hole transport layer 4 (HT1 with a thickness of 117nm) is deposited. Then, an electron blocking layer 5 (EB-1 with a thickness of 10nm) is deposited. After the electron blocking material is deposited, the light-emitting layer 6 of the OLED light-emitting device is fabricated. Its structure includes BH-1 as the host material and BD-1 as the dopant material, with a doping ratio of 3% by weight, and a film thickness of 20nm. After the light-emitting layer 6, HB-1 is deposited with a thickness of 8nm as the hole blocking layer 7. On top of the hole-blocking layer 7, ET-1 and Liq are further deposited by vacuum evaporation, with an ET-1 to Liq mass ratio of 1:1. The vacuum-deposited film thickness of this material is 30 nm, and this layer serves as the electron transport layer 8. On the electron transport layer 8, a LiF layer with a thickness of 1 nm is formed by vacuum evaporation, and this layer serves as the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a thickness of 16 nm is formed by vacuum evaporation, with a Mg to Ag mass ratio of 1:9, and this layer serves as the cathode layer 10. On the cathode layer 10, a 65 nm layer of CP-1 is vacuum-deposited as the CPL layer 11.

[0236] Comparative Examples of Devices 2-6, 11-13

[0237] The procedure was performed according to the method of Comparative Example 1, except that the organic material in the electron blocking layer was replaced with the organic material shown in Table 6.

[0238] Device Examples 1-22 were carried out according to the method of Device Comparative Example 1, except that the organic material in the electron blocking layer was replaced with the organic material shown in Table 6.

[0239]

[0240] After completing the OLED light-emitting device as described above, the anode and cathode are connected using a known driving circuit, and the current efficiency, emission spectrum, and lifetime of the device are measured.

[0241] Table 6

[0242]

[0243]

[0244] Taking device embodiment 1 as an example in the table above, "HI1:HT1=3:9710nm" in the second column indicates that the hole injection layer is made of compound HT1 and p-type doped material HI1, 3:97 refers to the weight ratio of p-type doped material HI1 to compound HT1 of 3:97, and 10nm represents the thickness of the layer; "110nm" in the fourth column indicates that the material used is compound 1, and the thickness of the layer is 10nm. The meanings in the other tables can be deduced similarly.

[0245] The technical effects of applying the compounds of the present invention to the hole transport layer are illustrated below through device comparative examples 7-10 and device examples 23-38.

[0246] The molecular structures of the materials involved in the following preparation process are shown below:

[0247]

[0248] Device Comparison Example 7

[0249] Organic electroluminescent devices are prepared according to the following steps:

[0250] like Figure 1As shown, substrate layer 1 is transparent glass. Anode layer 2 (Ag (100nm)) is washed sequentially with alkaline washing, pure water washing, drying, and then ultraviolet-ozone washing to remove organic residues from the surface of the anode layer. After the above washing, a hole injection layer 3 (HT-2 and HI1 with a mass ratio of 97:3) is deposited on anode layer 2 using a vacuum evaporation apparatus. Next, a hole transport layer 4 (HT-2 with a thickness of 117nm) is deposited. Then, an electron blocking layer 5 (EB-7 with a thickness of 10nm) is deposited. After the electron blocking materials are deposited, the light-emitting layer 6 of the OLED light-emitting device is fabricated. Its structure includes BH-1 as the host material and BD-1 as the dopant material, with a doping ratio of 3% by weight, and a light-emitting layer thickness of 20nm. After the light-emitting layer 6, HB-1 is deposited to a thickness of 8nm as the hole blocking layer 7. On top of the hole-blocking layer 7, ET-1 and Liq are further deposited by vacuum evaporation, with an ET-1 to Liq mass ratio of 1:1. The vacuum-deposited film thickness of this material is 30 nm, and this layer serves as the electron transport layer 8. On the electron transport layer 8, a LiF layer with a thickness of 1 nm is formed by vacuum evaporation, and this layer serves as the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a thickness of 16 nm is formed by vacuum evaporation, with a Mg to Ag mass ratio of 1:9, and this layer serves as the cathode layer 10. On the cathode layer 10, a 65 nm layer of CP-1 is vacuum-deposited as the CPL layer 11.

[0251] Device Comparison Examples 8-10

[0252] The procedure was performed according to the method of Comparative Example 7, except that the organic materials in the hole injection layer and the hole transport layer were replaced with the organic materials shown in Table 7.

[0253] Device Examples 23-42

[0254] The procedure was performed according to the method of Comparative Example 7, except that the organic materials in the hole injection layer and the hole transport layer were replaced with the organic materials shown in Table 7.

[0255] Table 7

[0256]

[0257]

[0258] Taking device embodiment 23 as an example in the table above, "HI1:138=3:9710nm" in the second column indicates that the material used for the hole injection layer is compound 138 and p-type doped material HI1, 3:97 refers to the weight ratio of p-type doped material to compound 128 is 3:97, and 10nm represents the thickness of the layer; "138117nm" in the third column indicates that the material used is compound 138, and the thickness of the layer is 117nm. The meanings in the other tables can be deduced similarly.

[0259] After fabricating the OLED light-emitting device as described above, the cathode and anode are connected using a known driving circuit, and various performance parameters of the device are measured.

[0260] The device measurement performance results of Examples 1-42 and Comparative Examples 1-10 are shown in Tables 8 and 9.

[0261] Table 8

[0262]

[0263]

[0264] Table 9

[0265]

[0266]

[0267] Note: Current efficiency and color coordinates were measured using an IVL (current-voltage-luminance) testing system (Suzhou Fushida Scientific Instruments Co., Ltd.), with a current density of 10 mA / cm² during testing. 2 The lifetime testing system is the EAS-62C OLED device lifetime tester from System Technology Inc. of Japan. LT95 refers to the time it takes for the device brightness to decay to 95% at a specific current density. The high-temperature lifetime test temperature is 85℃, and LT80 refers to the time it takes for the device brightness to decay to 80% at a specific current density.

[0268] As can be seen from the device data results in Table 8, Examples 1-22, compared with Device Comparison Examples 1-6 and 11-13, using the aromatic amine compounds of the present invention as electron blocking layer materials effectively improves device efficiency and lifetime due to their high carrier transport rate and excellent exciton blocking ability. In particular, the device lifetime is unexpectedly significantly improved.

[0269] As can be seen from the results in Table 9, using the aromatic amine organic compounds of the present invention as hole injection and hole transport layer materials effectively improves device efficiency and device lifetime due to their high carrier transport rate, especially effectively improving device efficiency and high-temperature lifetime.

Claims

1. An organic compound of an aromatic amine, characterized by, The structure of the organic compound is shown in general formula (1): General Formula (1) General Formula (2) In general formula (1), L1 and L2 each independently represent a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene; R1 represents a phenyl group, a naphthyl group, a bisphenyl group, a benzofuranyl group, a dibenzofuranyl group, a benzothienyl group, a dibenzothienyl group, a methyl-substituted fluorenyl group, a diphenylfluorenyl group, a carbazoyl group, or a spirofluorenyl group; R2 represents a substituted or unsubstituted phenyl group, a naphthyl group, a substituted or unsubstituted bisphenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a methyl-substituted fluorenyl group, a diphenylfluorenyl group, a substituted or unsubstituted carbazoyl group, or a substituted or unsubstituted spirofluorenyl group; Z1 to Z5 each independently represent a hydrogen atom or a deuterium atom; R4 represents a hydrogen atom, a deuterium atom, or a structure represented by general formula (2); R3 represents a hydrogen atom, a deuterium atom, a phenyl group, or a structure represented by general formula (2), and R3 and R4 are not simultaneously a hydrogen atom and a deuterium atom; n represents a number 0, 1, 2, or 3; and when R3 represents a phenyl group, n represents 0; and when R3 or R4 represents a structure represented by general formula (2), n does not represent 0; In general formula (2), X represents an oxygen atom or a sulfur atom; R6-R 13 each independently represents a hydrogen atom, a deuterium atom, a methyl group, an ethyl group, a tert-butyl group, an adamantyl group, a phenyl group, a naphthyl group, a biphenyl group, and R6-R 13 two adjacent groups can be bonded to each other to form a ring; the substituent of the substituted or unsubstituted group is optionally selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, a tert-butyl group, an adamantyl group, a phenyl group, a naphthyl group, a biphenyl group, a furanyl group, a thienyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, and a dibenzothienyl group.

2. An organic compound of an aromatic amine, characterized by, The structure of the organic compound is shown in general formula (1-2) or general formula (1-3): Formula (1-2) Formula (1-3) In general formula (1-2) and general formula (1-3), L1 and L2 each independently represent a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted biphenylene; R1 and R2 each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted bisphenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazoyl group, or a substituted or unsubstituted spirofluorenyl group; R4 each independently represents a hydrogen atom or a deuterium atom, R3 represents a hydrogen atom or a deuterium atom, n represents a number 1, 2, or 3; X represents an oxygen atom or a sulfur atom; R7-R 13 respectively, independently represent a hydrogen atom, a deuterium atom, a methyl group, an ethyl group, a tert-butyl group, an adamantyl group, a phenyl group, a naphthyl group, a biphenyl group, and two adjacent groups can be bonded to each other to form a ring; the substituent of the substituted or unsubstituted group is optionally selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, a tert-butyl group, an adamantyl group, a phenyl group, a naphthyl group, a biphenyl group, a furanyl group, a thienyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, and a dibenzothienyl group.

3. The organic compound according to claim 2, characterized by The structure of the organic compound is shown in general formula (1-4) or general formula (1-5): Formula (1-4) Formula (1-5) In general formula (1-4) and general formula (1-5), L1 and L2 each independently represent a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted biphenylene; R1, R2, respectively, independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazoyl group, a substituted or unsubstituted spirofluorenyl group; R4, respectively, independently represent a hydrogen atom, a deuterium atom, R3 represents a hydrogen atom, a deuterium atom, X represents an oxygen atom or a sulfur atom; R7-R 13 respectively, independently represent a hydrogen atom, a deuterium atom, a methyl group, an ethyl group, a tert-butyl group, an adamantyl group, a phenyl group, a naphthyl group, a biphenyl group, and two adjacent groups can be bonded to each other to form a ring; a substituent of the substituted or unsubstituted group is optionally selected from a deuterium atom, a methyl group, an ethyl group, a tert-butyl group, an adamantyl group, a phenyl group, a naphthyl group, a biphenyl group, a furanyl group, a thienyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, or a dibenzothienyl group.

4. The organic compound according to claim 1, wherein The structure of the organic compound is shown in General Formula (1-6): General Formula (1-6) In General Formula (1-6), L1, L2, respectively, independently represent a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group; R1 represents a phenyl group, a naphthyl group, a biphenyl group, a benzofuranyl group, a dibenzofuranyl group, a benzothienyl group, a dibenzothienyl group, a methyl-substituted fluorenyl group, a diphenyl fluorenyl group, a carbazoyl group, a spirofluorenyl group; R2 represents a substituted or unsubstituted phenyl group, a naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a methyl-substituted fluorenyl group, a diphenyl fluorenyl group, a substituted or unsubstituted carbazoyl group, a substituted or unsubstituted spirofluorenyl group; a substituent of the substituted or unsubstituted group is optionally selected from a deuterium atom, a methyl group, an ethyl group, a tert-butyl group, an adamantyl group, a phenyl group, a naphthyl group, a biphenyl group, a furanyl group, a thienyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, or a dibenzothienyl group.

5. The organic compound according to claim 1, wherein The structure of the organic compound is shown in General Formula (1-7) or General Formula (1-8): General Formula (1-7) General Formula (1-8) In General Formula (1-7) and General Formula (1-8), L1, L2, respectively, independently represent a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group; R2 represents a substituted or unsubstituted phenyl group, a naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a methyl-substituted fluorenyl group, a diphenyl fluorenyl group, a substituted or unsubstituted carbazoyl group, a substituted or unsubstituted spirofluorenyl group; X1represents an oxygen atom, a sulfur atom, N-R 16 or C(R 14 ); R 15 ); R 14 , R 15 represents methyl or phenyl, R 16 represents substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl; Z represents a carbon atom or C-R0; R0 represents a hydrogen atom, a deuterium atom, a methyl group, an ethyl group, a tert-butyl group, an adamantyl group, and adjacent two R0 can be bonded to each other to form a ring; a substituent of the substituted or unsubstituted group is optionally selected from a deuterium atom, a methyl group, an ethyl group, a tert-butyl group, an adamantyl group, a phenyl group, a naphthyl group, a biphenyl group, a furanyl group, a thienyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, or a dibenzothienyl group.

6. The organic compound according to claim 1, wherein The structure of the organic compound is shown in General Formula (1-9), General Formula (1-10), General Formula (1-11), General Formula (1-12), or General Formula (1-13): General Formula (1-9) General Formula (1-10) General Formula (1-11) General Formula (1-12) General Formula (1-13) In General Formula (1-9), General Formula (1-10), General Formula (1-11), General Formula (1-12), and General Formula (1-13), L1and L2independently represent a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene. R2represents a substituted or unsubstituted phenyl, naphthyl, substituted or unsubstituted bipyridyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothienyl, methyl-substituted fluorenyl, diphenylfluorenyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted spirofluorenyl. R represents a hydrogen atom. The substituent of the substituted or unsubstituted group is optionally selected from a deuterium atom, a methyl group, an ethyl group, a tert-butyl group, an adamantyl group, a phenyl group, a naphthyl group, a biphenyl group, a furanyl group, a thienyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, or a dibenzothienyl group.

7. The organic compound according to claim 1, wherein R2represents a substituted or unsubstituted phenyl, naphthyl, substituted or unsubstituted bipyridyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothienyl, methyl-substituted fluorenyl, diphenylfluorenyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted spirofluorenyl. R1represents a phenyl group, a naphthyl group, or a bipyridyl group. R6-R 13 respectively, independently represent a hydrogen atom, a deuterium atom, a methyl group, an ethyl group, a tert-butyl group, an adamantyl group, a phenyl group, a naphthyl group, a biphenyl group; The substituent of the substituted or unsubstituted group is optionally selected from a deuterium atom, a methyl group, an ethyl group, a tert-butyl group, an adamantyl group, a phenyl group, a naphthyl group, a biphenyl group, a furanyl group, a thienyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, or a dibenzothienyl group.

8. The organic compound according to claim 1, wherein The structure of the organic compound is shown in General Formula (1-14) and General Formula (1-15): Formula (1-14) Formula (1-15) In General Formula (1-14) and General Formula (1-15), L2represents a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene. R2represents a substituted or unsubstituted phenyl, naphthyl, substituted or unsubstituted bipyridyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothienyl, methyl-substituted fluorenyl, diphenylfluorenyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted spirofluorenyl. R represents a hydrogen atom. The substituent of the substituted or unsubstituted group is optionally selected from a deuterium atom, a methyl group, an ethyl group, a tert-butyl group, an adamantyl group, a phenyl group, a naphthyl group, a biphenyl group, a furanyl group, a thienyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, or a dibenzothienyl group.

9. The organic compound according to claim 5, wherein The structure of the organic compound is shown in General Formula (1-16): General formula (1-16) In General Formula (1-16), L1and L2independently represent a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene. R2represents a substituted or unsubstituted phenyl group, a naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a methyl-substituted fluorenyl group, a diphenylfluorenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted spirofluorenyl group; X1represents an oxygen atom, a sulfur atom, N-R 16 or C(R 14 R 15 ); R 14 , R 15 represents a methyl group or a phenyl group, R 16 represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group; Z represents a carbon atom or C-R0; R0represents a hydrogen atom, a deuterium atom, a methyl group, an ethyl group, a tert-butyl group, or an adamantyl group, and two adjacent R0may be bonded to each other to form a ring; the substituent of the substituted or unsubstituted group is optionally selected from a deuterium atom, a methyl group, an ethyl group, a tert-butyl group, an adamantyl group, a phenyl group, a naphthyl group, a biphenyl group, a furanyl group, a thienyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, or a dibenzothienyl group.

10. An organic compound of an aromatic amine, characterized by, The compound has a specific structure as follows: (1) (2) (3) (4) (5) (6) (7) (8) (9) (10) (11) (12) (13) (14) (15) (16) (17) (18) (19) (20) (21) (22) (23) (24) (25) (26) (27) (28) (29) (30) (31) (32) (33) (34) (35) (36) (37) (38) (39) (40) (41) (42) (43) (44) (45) (46) (47) (48) (49) (50) (51) (52) (53) (54) (55) (56) (57) (58) (59) (60) (61) (62) (63) (64) (65) (66) (67) (68) (69) (70) (71) (72) (73) (74) (75) (76) (77) (78) (79) (80) (81) (82) (83) (84) (85) (86) (87) (88) (89) (90) (91) (92) (93) (94) (95) (96) (97) (98) (99) (100) (101) (102) (103) (104) (105) (106) (107) (108) (109) (110) (111) (112) (113) (114) (115) (116) (117) (118) (119) (120) (121) (122) (123) (124) (125) (126) (127) (128) (129) (130) (131) (132) (133) (134) (135) (136) (137) (138) (139) (140) (141) (142) (143) (144) (145) (146) (147) (148) (149) (150) (151) (152) (153) (154) (155) (156) (157) (158) (159) (160) (161) (162) (163) (164) (165) (166) (167) (168) (169) (170) (171) (172) (173) (174) (175) (176) (177) (178) (179) (180) (181) (182) (183) (184) (185) (186) (187) (188) (189) (190) (191) (192) (193) (194) (195) (196) (197) (198) (199) (200) (201) (202) (203) (204) (205) (206) (207) (208) (209) (210) (211) (212) (213) (214) (215) (216) (217) (218) (219) (220) (221) (222) (223) (224) (225) (226) (227) (228) (229) (230) (231) (232) (233) (234) (235) (236) (237) (238) (239) (240) (241) (242) (243) (244) (245) (246) (247) (248) (249) (250) (251) (252) (253) (254) (255) (256) (257) (258) (259) (260) (261) (262) (263) (264) (265) (266) (267) (268) (269) (270) (271) (272) (273) (274) (275) (276) (277) (278) (279) (280) (281) (282) (283) (284) (285) (286) (287) (288) (289) (290) (291) (292) (293) (294) (295) (296) (297) (298) (299) (300) (301) (302) (303) (304) (305) (306) (307) (308) (309) (310) (311) (312) (313) (314) (315) (316) (317) (318) (319) (320) (321) (322) (323) (324) (325) (326) (327) (328) (329) (330) (359) (380) (381) (382) (383) (384) (386) (388) (389) (390) (391) (392) (393) (394) (395) (396) (397) (398) (399) (400) 。 11. An organic electroluminescent device comprising a cathode, an anode and an organic functional layer, the organic functional layer being located between the cathode and the anode, characterized in that The organic electroluminescent device comprises at least one organic functional layer comprising the aromatic amine-based organic compound according to any one of claims 1 to 10. The organic functional layer comprises a hole transport region, a light-emitting region, and an electron transport region, and the hole transport region comprises the aromatic amine-based compound according to any one of claims 1 to 10.

12. The organic electroluminescent device according to claim 11, wherein The hole transport region comprises a hole injection layer, a hole transport layer, and an electron blocking layer, and the electron blocking layer comprises the aromatic amine-based compound according to claim 2 or 3.

13. The organic electroluminescent device according to claim 11, wherein The hole transport region comprises a hole injection layer, a hole transport layer, and an electron blocking layer, and the hole transport layer comprises the aromatic amine-based compound according to any one of claims 4 to 7.

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