Organic light-emitting device containing asymmetric bis-arylamine substituted dibenzofuran compound

Abstract

The invention provides an organic light-emitting device containing an asymmetric bis-arylamine substituted dibenzofuran compound, which comprises a hole transport layer, and the material of the hole transport layer comprises a compound as shown in a formula (I). According to the organic light-emitting device provided by the invention, the hole transport layer material is the asymmetric bis-arylamine substituted dibenzofuran compound, has efficient hole transport capability, can effectively improve the luminous efficiency of the organic light-emitting device, has a relatively shallow energy level, and can be better matched with an adjacent layer electrode material for use, so that the light-emitting efficiency of the organic light-emitting device is improved. The hole transport performance of the organic light-emitting device can be effectively improved, the light-emitting efficiency of the organic light-emitting device is improved, the driving voltage of the organic light-emitting device is reduced, and the service life of the organic light-emitting device is prolonged. # imgabs0 #

Description

[0001] This application claims priority to the Chinese patent application with patent number 202310799117.X filed on June 30, 2023. Technical Field

[0002] The present application relates to the technical field of organic light-emitting display, and in particular to an organic electroluminescent device comprising an asymmetric diphenylamine-substituted dibenzofuran compound and a display device comprising the same. Background Art

[0003] Electroluminescence (EL) refers to the phenomenon that luminescent materials emit light under the action of electric field, stimulated by current and voltage. It is a luminescence process that directly converts electrical energy into light energy. Organic electroluminescent displays (hereinafter referred to as OLEDs) have a series of advantages such as autonomous luminescence, low-voltage DC drive, full curing, wide viewing angle, light weight, simple composition and process. Compared with liquid crystal displays, organic electroluminescent displays do not require backlight sources, have large viewing angles, low power consumption, and their response speed can reach 1000 times that of liquid crystal displays, but their manufacturing cost is lower than that of liquid crystal displays with the same resolution. Therefore, organic electroluminescent devices have a very broad application prospect.

[0004] As OLED technology continues to advance in the two major fields of lighting and display, people are paying more attention to high-efficiency organic materials that affect the performance of OLED devices. Optimizing the device structure and matching various organic materials can produce organic electroluminescent devices with high efficiency and long life, which poses great opportunities and challenges for chemists to design and develop functional materials of various structures. How to develop high-efficiency organic materials to improve the luminous efficiency of organic electroluminescent devices and extend their service life has become a technical problem that technicians in this field need to solve urgently. Summary of the invention

[0005] The purpose of the present application is to provide an organic electroluminescent device comprising an asymmetric diphenylamine-substituted dibenzofuran compound and a display device comprising the same, so as to improve the luminous efficiency of the organic electroluminescent device and prolong its service life.

[0006] The first aspect of the present application provides an organic electroluminescent device, wherein the organic electroluminescent device comprises a hole transport layer, wherein the hole transport layer material comprises a compound of formula (I):

[0007]

[0008] in,

[0009] Ar 1 and Ar 2 Each independently selected from C6-C30 Aryl;

[0010] R 1 -R 5 are each independently selected from hydrogen, deuterium, C1-C6 alkyl, C1-C6 alkenyl, C6-C6 unsubstituted or substituted by Rc 30 Aryl, unsubstituted or Rc-substituted C3-C 30 heteroaryl, and the adjacent R 1 -R 5 They can be connected to form a ring;

[0011] R 6 -R 7 Each independently selected from hydrogen, deuterium, C1-C6 alkyl, C5-C 20 Cycloalkyl, C1-C6 alkenyl, unsubstituted or Rc-substituted C6-C 30 Aryl, unsubstituted or Rc-substituted C3-C 30 heteroaryl, and R 6 and R 7 They can be connected to form a ring;

[0012] R 8 and R 9 are each independently selected from hydrogen, deuterium, C1-C6 alkyl, C1-C6 alkenyl, C6-C6 unsubstituted or substituted by Rc 30 Aryl, unsubstituted or Rc-substituted C3-C 30 heteroaryl, and R 8 and R 9 They can be connected to form a ring;

[0013] R' and R" are each independently selected from C1-C6 alkyl, C5-C 20 Cycloalkyl, unsubstituted or substituted by Rc C6-C 30 Aryl, unsubstituted or Rc-substituted C3-C 30 Heteroaryl, and R' and R" may be connected to form a ring;

[0014] L 1 and L 2 Each independently selected from a chemical bond, a C6-C 30 arylene;

[0015] R a ', R b ', R c ', R d 'are each independently selected from hydrogen, deuterium, C1-C6 alkyl, C1-C6 alkenyl, C6-C6 unsubstituted or substituted by Rc 30 Aryl, and the adjacent R a ', Rb ', R c ', R d ' can be connected to form a ring;

[0016] The heteroatoms on the heteroaryl group are each independently selected from O, S or N;

[0017] The substituents Rc of each group are each independently selected from deuterium, halogen, C1-C4 alkyl, phenyl, biphenyl, terphenyl, pyridyl, pyrimidyl or naphthyl.

[0018] A second aspect of the present application provides a display device, which includes the organic electroluminescent device provided in the first aspect of the present application.

[0019] The organic electroluminescent device provided by the present application has a hole transport layer material of an asymmetric diphenylamine substituted dibenzofuran compound, which has a highly efficient hole transport capability and can effectively improve the luminous efficiency of the organic electroluminescent device. At the same time, it has a shallow energy level and can be better used with adjacent layer materials, which can effectively improve the hole transport performance of the organic electroluminescent device, improve the luminous efficiency of the organic electroluminescent device, reduce its driving voltage and extend its service life. The display device provided by the present application has an excellent display effect.

[0020] Of course, implementing any product or method of the present application does not necessarily require achieving all of the advantages described above at the same time. BRIEF DESCRIPTION OF THE DRAWINGS

[0021] In order to more clearly illustrate the technical solution in the present application, the drawings required for use in the description of the embodiments will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present application. For ordinary technicians in this field, other embodiments can also be obtained based on these drawings.

[0022] Figure 1 A schematic diagram of the structure of a typical organic electroluminescent device. DETAILED DESCRIPTION

[0023] The following will be combined with the drawings in this application to clearly and completely describe the technical solutions in this application. Obviously, the described embodiments are only part of the embodiments of this application, not all of the embodiments. All other embodiments obtained by ordinary technicians in this field based on this application belong to the scope of protection of this application.

[0024] In a first aspect, the present application provides an organic electroluminescent device, wherein the organic electroluminescent device comprises a hole transport layer, wherein the hole transport layer material comprises a compound of formula (I):

[0025]

[0026] in,

[0027] Ar 1 and Ar 2 Each independently selected from C6-C 30 Aryl;

[0028] R 1 -R 5 are each independently selected from hydrogen, deuterium, C1-C6 alkyl, C1-C6 alkenyl, C6-C6 unsubstituted or substituted by Rc 30 Aryl, unsubstituted or Rc-substituted C3-C 30 heteroaryl, and the adjacent R 1 -R 5 They can be connected to form a ring;

[0029] R 6 and R 7 Each independently selected from hydrogen, deuterium, C1-C6 alkyl, C5-C 20 Cycloalkyl, C1-C6 alkenyl, unsubstituted or Rc-substituted C6-C 30 aryl, unsubstituted or Rc-substituted C3-C 30 The heteroaryl group, and R 6 and R 7 They can be connected to form a ring;

[0030] R 8 and R 9 are each independently selected from hydrogen, deuterium, C1-C6 alkyl, C1-C6 alkenyl, C6-C6 unsubstituted or substituted by Rc 30 Aryl, unsubstituted or Rc-substituted C3-C 30 heteroaryl, and R 8 and R 9 They can be connected to form a ring;

[0031] R' and R" are each independently selected from C1-C6 alkyl, C5-C 20 Cycloalkyl, unsubstituted or substituted by Rc C6-C 30 Aryl, unsubstituted or Rc-substituted C3-C 30 Heteroaryl, and R' and R" may be connected to form a ring;

[0032] L 1 and L 2 Each independently selected from a chemical bond, a C6-C 30 arylene;

[0033] R a ', R b ', R c ', Rd 'are each independently selected from hydrogen, deuterium, C1-C6 alkyl, C1-C6 alkenyl, C6-C6 unsubstituted or substituted by Rc 30 Aryl, and adjacent R a ', R b ', R c ', R d ' can be connected to form a ring;

[0034] The heteroatoms on the heteroaryl group are each independently selected from O, S or N;

[0035] The substituents Rc of each group are each independently selected from deuterium, halogen, C1-C4 alkyl, phenyl, biphenyl, terphenyl, pyridyl, pyrimidyl or naphthyl.

[0036] Preferably, Ar 1 and Ar 2 Each independently selected from C6-C 18 Aryl.

[0037] Preferably, R 1 -R 5 are each independently selected from hydrogen, deuterium, C1-C6 alkyl, C1-C6 alkenyl, C6-C6 unsubstituted or substituted by Rc 18 Aryl, unsubstituted or Rc-substituted C3-C 18 heteroaryl, and the adjacent R 1 -R 5 They can be connected to form a ring.

[0038] Preferably, R 6 and R 7 Each independently selected from hydrogen, deuterium, C1-C6 alkyl, C5-C 20 Cycloalkyl, C1-C6 alkenyl, unsubstituted or Rc-substituted C6-C 18 Aryl, unsubstituted or Rc-substituted C3-C 18 heteroaryl, and R 6 and R 7 They can be connected to form a ring.

[0039] Preferably, R 8 and R 9 are each independently selected from hydrogen, deuterium, C1-C6 alkyl, C1-C6 alkenyl, C6-C6 unsubstituted or substituted by Rc 18 Aryl, unsubstituted or Rc-substituted C3-C 18 heteroaryl, and R 8 and R 9 They can be connected to form a ring;

[0040] Preferably, R' and R" are each independently selected from C1-C6 alkyl, C5-C 10 Cycloalkyl, unsubstituted or substituted by Rc C6-C 18 Aryl, unsubstituted or Rc-substituted C3-C 18 Heteroaryl, and R' and R" may be connected to form a ring;

[0041] Preferably, L 1 and L 2 Each independently selected from a chemical bond, a C6-C 18 Arylene.

[0042] Preferably, R a ', R b ', R c ', R d 'are each independently selected from hydrogen, deuterium, C1-C6 alkyl, C1-C6 alkenyl, C6-C6 unsubstituted or substituted by Rc 18 Aryl, and adjacent R a ', R b ', R c ', R d ' can be connected to form a ring.

[0043] More preferably, Ar 1 and Ar 2 A group each independently selected from the following compounds which are unsubstituted or substituted with Rc: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, 9,9-dimethylfluorene, spirofluorene.

[0044] More preferably, R 1 -R 5 Each independently selected from hydrogen, deuterium, methyl, ethyl, propyl, vinyl, propenyl, butenyl, a group of the following compounds which are unsubstituted or substituted with Rc: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, anthracene, dibenzofuran, dibenzothiophene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, spirofluorene, and the adjacent R 1 -R 5 They can be connected to form a ring.

[0045] More preferably, R 6 and R 7 each independently selected from hydrogen, deuterium, methyl, ethyl, propyl, cyclopentyl, cyclohexyl, vinyl, propenyl, butenyl, a group of the following compounds which are unsubstituted or substituted with Rc: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, pyridine, benzofuran, dibenzofuran, aza-dibenzofuran, benzothiophene, dibenzothiophene, aza-dibenzothiophene, 9,9-dimethylfluorene, spirofluorene, aromatic amine, carbazole, and R 6 and R 7They can be connected to form a ring.

[0046] More preferably, R 8 and R 9 Each independently selected from hydrogen, deuterium, methyl, ethyl, propyl, vinyl, propenyl, butenyl, the following compound groups which are unsubstituted or substituted by Rc: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, pyridine, benzofuran, dibenzofuran, aza-dibenzofuran, benzothiophene, dibenzothiophene, aza-dibenzothiophene, 9,9-dimethylfluorene, spirofluorene, aromatic amine, carbazole, R 8 and R 9 They can be connected to form a ring.

[0047] More preferably, R' and R" are each independently selected from methyl, ethyl, propyl, cyclopentyl, cyclohexyl, a group of the following compounds which are unsubstituted or substituted with Rc: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, dibenzofuran, benzothiophene, dibenzothiophene, 9,9-dimethylfluorene, spirofluorene, aromatic amine, carbazole, and R' and R" may be connected to form a ring.

[0048] More preferably, L 1 and L 2 Each subunit is independently selected from the following compounds which are chemically bonded, unsubstituted or substituted by Rc: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, 9,9-dimethylfluorene, spirofluorene, aromatic amine, and carbazole.

[0049] More preferably, R a ', R b ', R c ', R d 'are each independently selected from hydrogen, deuterium, methyl, ethyl, propyl, vinyl, propenyl, butenyl, a group of the following compounds which are unsubstituted or substituted with Rc: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, 9,9-dimethylfluorene, spirofluorene, and the adjacent R a ', R b ', R c ', R d ' can be connected to form a ring.

[0050] In some embodiments of the present application, the thickness of the hole transport layer is 60 nm-100 nm.

[0051] In some embodiments of the present application, the compound of formula (I) may be selected from the compounds shown in the following A1 to A30:

[0052]

[0053]

[0054] The present application provides an organic electroluminescent device comprising an asymmetric diarylamine substituted dibenzofuran compound, which comprises at least one of the hole transport layer materials provided in the present application. The hole transport layer material provided in the present application has an efficient hole transport capability, can effectively improve the luminous efficiency of the organic electroluminescent device, and has a shallow energy level, can be used in combination with adjacent layer materials, can effectively improve the hole transport performance of the organic electroluminescent device, improve the luminous efficiency of the organic electroluminescent device, reduce its driving voltage and extend its service life. Therefore, the organic electroluminescent device provided in the present application has a low driving voltage, high luminous efficiency and a long service life.

[0055] In the present application, there is no particular limitation on the type and structure of the organic electroluminescent device, and it can be an organic electroluminescent device of different types and structures known in the art, as long as at least one of the hole transport layer materials provided in the present application can be used.

[0056] The organic electroluminescent device of the present application may be a light-emitting device with a top, bottom or double-sided light-emitting structure, and its structure is not particularly limited. For example, it may include an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode in sequence on a substrate, and may also include a hole blocking layer, an electron blocking layer, etc.

[0057] In the organic electroluminescent device of the present application, except for the hole transport layer comprising the hole transport material provided in the present application, other layers may use any material used for the layers in the prior art.

[0058] In addition, the organic electroluminescent device of the present application may have an electron blocking layer between the hole transport layer and the light-emitting layer, a hole blocking layer between the light-emitting layer and the electron transport layer, a light extraction layer may be provided on the transparent electrode on the light-emitting side, and an electron injection layer may or may not be provided between the electron transport layer and the cathode. However, the structure of the organic electroluminescent device of the present application is not limited to the above-mentioned specific structure, and the above-mentioned layers may be omitted or increased if necessary. The present application has no particular limitation on the thickness of the above-mentioned layers, as long as the purpose of the present application can be achieved. For example, an organic electroluminescent device may include, on a substrate, in sequence, an anode (100 nm to 150 nm) made of metal, a hole injection layer (5 nm to 20 nm), a hole transport layer (80 nm to 140 nm), an electron blocking layer (5 nm to 20 nm), a light-emitting layer (20 nm to 45 nm), a hole blocking layer (5 nm to 20 nm), an electron transport layer (20 nm to 80 nm), an electron injection layer (0.5 nm to 20 nm), a transparent or semi-transparent cathode (100 nm to 160 nm), and a light extraction layer (50 nm to 90 nm).

[0059] Figure 1A schematic diagram of a typical organic electroluminescent device is shown, wherein, from bottom to top, a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode 8 are arranged in sequence.

[0060] Understandably, Figure 1 The structure of a typical organic electroluminescent device is schematically shown, and the present application is not limited to this structure. The hole transport layer material of the present application can be used in any type of organic electroluminescent device. For example, the organic electroluminescent device may also include an electron blocking layer, a hole blocking layer, a light extraction layer, etc. In actual application, these layers may be added or omitted according to specific circumstances.

[0061] For convenience, the following reference Figure 1 The organic electroluminescent device of the present application is described, but this does not mean any limitation on the protection scope of the present application. It can be understood that all organic electroluminescent devices that can use the hole transport material of the present application are within the protection scope of the present application.

[0062] In the present application, there is no particular limitation on the substrate 1 , and any conventional substrate used in organic electroluminescent devices in the prior art may be used.

[0063] In the present application, there is no particular restriction on the material of the anode 2, and anode materials known in the art can be used. The anode 2 can be a multilayer structure, and the present application has no particular restriction on the number of layers of the multilayer structure, which can be selected according to actual needs, as long as it can meet the purpose of the present application, for example, 1 layer, 2 layers, 3 layers or more layers.

[0064] In the present application, there is no particular limitation on the material of the hole injection layer 3 , and hole injection materials known in the art, hole transport materials (HTM) known in the art, or hole transport layer materials provided in the present application may be used.

[0065] In the present application, the material of the hole injection layer 3 may also include a p-type dopant. The present application has no particular restrictions on the type of the p-type dopant, and various p-type dopants known in the art may be used. For example, the p-type dopant may be selected from but not limited to at least one of the following p-1 to p-3 compounds:

[0066]

[0067] In the present application, there is no particular limitation on the amount of the p-type dopant, which may be an amount known to those skilled in the art.

[0068] In the present application, the material of the hole transport layer 4 may also include hole transport materials (HTM) known in the art. The present application does not specifically limit the number of layers of the hole transport layer, which can be adjusted according to actual needs as long as the purpose of the present application can be met, for example, 1 layer, 2 layers, 3 layers, 4 layers or more layers.

[0069] In the present application, there is no particular restriction on the material of the light-emitting layer 5, and each of them may include a light-emitting layer host material and a light-emitting layer guest material, wherein the amount of the light-emitting layer host material and the light-emitting layer guest material is not particularly limited, and may be an amount known to those skilled in the art. In the present application, the light-emitting layer 5 may include a blue light-emitting layer, a green light-emitting layer, or a red light-emitting layer, and there is no particular restriction on the light-emitting material in the light-emitting layer 5, and various light-emitting materials known to those skilled in the art may be used.

[0070] In the present application, there is no particular restriction on the material of the electron transport layer 6, and electron transport materials known in the art can be used. In the present application, the electron transport layer 6 can also include an n-type dopant, and the present application does not particularly limit the type of the n-type dopant, and various n-type dopants known in the art can be used.

[0071] In the present application, there is no particular limitation on the material of the electron injection layer 7 , and any electron injection material known in the art can be used.

[0072] In the present application, there is no particular limitation on the material of the cathode 8, and cathode materials known in the art can be used.

[0073] The second aspect of the present application provides a display device, which includes the organic electroluminescent device provided in the first aspect of the present application. The display device includes but is not limited to a display, a television, a tablet computer, a mobile communication terminal, etc.

[0074] The method for preparing the organic electroluminescent device of the present application is not particularly limited, and any method known in the art may be used. For example, the present application may be prepared by the following preparation method:

[0075] (1) cleaning the anode 2 on the substrate 1 of the top-emitting OLED device by using a cleaning machine through steps such as chemical cleaning, water cleaning, brushing, high-pressure water cleaning, and air knife cleaning, and then performing a heat treatment;

[0076] (2) vacuum evaporating the material of the hole injection layer 3 on the anode 2 to form the hole injection layer 3;

[0077] (3) vacuum evaporating the material of the hole transport layer 4 on the hole injection layer 3 to form the hole transport layer 4;

[0078] (4) vacuum evaporating a light-emitting layer 5 on the hole transport layer 4, wherein the light-emitting layer 5 comprises a light-emitting layer host material and a light-emitting layer guest material;

[0079] (5) vacuum evaporating the material of the electron transport layer 6 on the light emitting layer 5 to form the electron transport layer 6;

[0080] (6) vacuum evaporating the material of the electron injection layer 7 on the electron transport layer 6 to form the electron injection layer 7;

[0081] (7) The cathode 8 is formed by vacuum evaporating the material of the cathode 8 on the electron injection layer 7 .

[0082] The above only describes a typical structure of an organic electroluminescent device and its preparation method. It should be understood that the present application is not limited to this structure. The hole transport material of the present application can be used in an organic electroluminescent device of any structure, and the organic electroluminescent device can be prepared by any preparation method known in the art.

[0083] The synthesis method of the compound of the present application is not particularly limited, and any method known to those skilled in the art can be used for synthesis. The following examples illustrate the synthesis process of the compound of the present application.

[0084] Synthesis example

[0085] Synthesis of Compound A1

[0086]

[0087] Add 100mmol of 2-iodo-4-bromophenol, 100mmol of 2-fluoro-4-chlorophenylboric acid, 41.4g of potassium carbonate (300mmol), 800mL of tetrahydrofuran (THF) and 200mL of water to a reaction flask, and add 1mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4). React at 60°C for 12h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, concentrate the organic phase to obtain a white solid, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain a white powder M1. Among them, the amount of Pd(PPh3)4 added is 1mol% of 2-iodo-4-bromophenol.

[0088] Add 100 mmol of M1, 300 mL of N,N-dimethylformamide (DMF), and 41.4 g of potassium carbonate (300 mmol) to the reaction bottle and react at 120°C for 12 hours. After the reaction is completed, add water, solid precipitates, and filter to obtain intermediate M2.

[0089] Add 100mmol of 2-amino-9,9-dimethylfluorene, 100mmol of 4-bromobiphenyl, 28.83g of sodium tert-butoxide (300mmol), 800mL of toluene, and add 1mol% of bis(dibenzylideneacetone)palladium (Pd(dba)2) to the reaction flask. React at 100°C for 12h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M3. Among them, the amount of Pd(dba)2 added is 1mol% of 2-amino-9,9-dimethylfluorene.

[0090] Add 100 mmol of M2, 100 mmol of M3, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M4. Among them, the amount of Pd(dba)2 added is 1 mol% of M2.

[0091] Add 100 mmol of M4, 100 mmol of diphenylamine, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to a reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain a white powder A1. The amount of Pd(dba)2 added is 1 mol% of M4.

[0092] 1 H NMR (400MHz, Chloroform) δ8.21(s,1H),8.02(s,1H),7.91(d,J=7.2Hz,1H),7.86(d,J=8.4Hz,1H),7.70(d,J=7.2H z,2H),7.58-7.50(m,5H),7.48-7.27(m,8H),7.28-7.20(m,6H),7.15(d,J=8.0Hz,1H),7.08(d,J=7.6Hz,4H),7.00 7.70(t,J=7.2Hz,2H),1.69(s,6H).

[0093] M / Z: Exp., 693.7; Calc., 694.3.

[0094] Synthesis of Compound A4

[0095]

[0096] Add 100mmol of 2-iodo-4-bromophenol, 100mmol of 2-fluoro-4-chlorophenylboronic acid, 41.4g of potassium carbonate (300mmol), 800mL of THF and 200mL of water to a reaction flask, and add 1mol% of Pd(PPh3)4. React at 60°C for 12h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, concentrate the organic phase to obtain a white solid, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain a white powder M1. Among them, the amount of Pd(PPh3)4 added is 1mol% of 2-iodo-4-bromophenol.

[0097] 100 mmol of M1, 300 mL of DMF, and 41.4 g of potassium carbonate (300 mmol) were added to the reaction flask and reacted at 120° C. for 12 h. After the reaction was completed, water was added, and solid precipitated, which was filtered to obtain intermediate M2.

[0098] Add 100 mmol of 2-bromo-fluorenone and 200 mL of THF to the reaction flask, and then dropwise add 110 mmol of methylmagnesium bromide at 0°C. After the addition is complete, warm the temperature to room temperature and react for 12 hours. After the reaction is complete, add water, separate the organic phase, and concentrate to obtain intermediate M3.

[0099] Add 100 mmol of M3 and 100 mmol of dibenzothiophene to the reaction flask, cool to 0°C, drop boron tribromide, stir at room temperature, and react for 12 hours. After the reaction is complete, add water, separate the organic phase, dry, and concentrate to obtain intermediate M4.

[0100] Add 100 mmol of 2-naphthylamine, 100 mmol of M4, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M5. Among them, the amount of Pd(dba)2 added is 1 mol% of M4.

[0101] Add 100 mmol of M2, 100 mmol of M5, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M6. Among them, the amount of Pd(dba)2 added is 1 mol% of M2.

[0102] Add 100 mmol of M6, 100 mmol of diphenylamine, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to a reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder A4. Among them, the amount of Pd(dba)2 added is 1 mol% of M6.

[0103] 1 H NMR(400MHz,Chloroform)δ8.45(d,J=7.6Hz,1H),8.21(d,J=7.2Hz,2H),8.05(s,1H),7.96(d,J=6.4Hz,1H),7.88(d,J=8.0Hz,2H),7 .78(d,J=8.1Hz,1H),7.70(d,J=6.8Hz,2H),7.65-7.50(m,5H),7.48-7.35(m,5H),7.32-7.18(m,9H),7.15-6.95(m,8H),2.28(s,3H).

[0104] M / Z: Exp., 836.0; Calc., 836.3.

[0105] Synthesis of Compound A6

[0106]

[0107] Add 100mmol of 2-iodo-4-bromophenol, 100mmol of 2-fluoro-4-chlorophenylboronic acid, 41.4g of potassium carbonate (300mmol), 800mL of THF and 200mL of water to a reaction flask, and add 1mol% of Pd(PPh3)4. React at 60°C for 12h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, concentrate the organic phase to obtain a white solid, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain a white powder M1. Among them, the amount of Pd(PPh3)4 added is 1mol% of 2-iodo-4-bromophenol.

[0108] 100 mmol of M1, 300 mL of DMF, and 41.4 g of potassium carbonate (300 mmol) were added to the reaction flask and reacted at 120° C. for 12 h. After the reaction was completed, water was added, and solid precipitated, which was filtered to obtain intermediate M2.

[0109] Add 100 mmol of 2-bromo-fluorenone and 200 mL of THF to the reaction flask, and then dropwise add 110 mmol of methylmagnesium bromide at 0°C. After the addition is complete, warm the temperature to room temperature and react for 12 hours. After the reaction is complete, add water, separate the organic phase, and concentrate to obtain intermediate M3.

[0110] Add 100 mmol of M3 and 200 mL of benzene to the reaction flask, cool to 0°C, drop boron tribromide, stir at room temperature, and react for 12 hours. After the reaction is complete, add water, separate the organic phase, dry, and concentrate to obtain intermediate M4.

[0111] Add 100 mmol of 4-benzidine, 100 mmol of M4, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M5. Among them, the amount of Pd(dba)2 added is 1 mol% of M4.

[0112] Add 100 mmol of M2, 100 mmol of M5, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M6. Among them, the amount of Pd(dba)2 added is 1 mol% of M2.

[0113] Add 100 mmol of M6, 100 mmol of diphenylamine, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to a reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder A6. The amount of Pd(dba)2 added is 1 mol% of M6.

[0114] 1H NMR (400MHz, Chloroform) δ8.23(s,1H),8.04(s,1H),7.91(d,J=7.2Hz,1H),7.88(d,J=8.4Hz,1H),7.75(d,J=7.6Hz,2H),7.61-7. 50(m,5H),7.48-7.31(m,8H),7.28-7.19(m,10H),7.14(t,J=7.6Hz,2H),7.10(d,J=7.2Hz,4H),7.35(t,J=7.2Hz,2H),2.28(s,3H).

[0115] M / Z: Exp., 756.1; Calc., 756.3.

[0116] Synthesis of Compound A9

[0117]

[0118] Add 100mmol of 2-iodo-4-bromophenol, 100mmol of 2-fluoro-4-chlorophenylboronic acid, 41.4g of potassium carbonate (300mmol), 800mL of THF and 200mL of water to a reaction flask, and add 1mol% of Pd(PPh3)4. React at 60°C for 12h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, concentrate the organic phase to obtain a white solid, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain a white powder M1. Among them, the amount of Pd(PPh3)4 added is 1mol% of 2-iodo-4-bromophenol.

[0119] Add 100 mmol of M1, 300 mL of N,N-dimethylformamide (DMF), and 41.4 g of potassium carbonate (300 mmol) to the reaction bottle and react at 120°C for 12 hours. After the reaction is completed, add water, solid precipitates, and filter to obtain intermediate M2.

[0120] Add 100 mmol of 2-amino-9,9-dimethylfluorene, 100 mmol of 2-bromonaphthalene, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of toluene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 100°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M3. Among them, the amount of Pd(dba)2 added is 1 mol% of 2-amino-9,9-dimethylfluorene.

[0121] Add 100 mmol of M2, 100 mmol of M3, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M4. Among them, the amount of Pd(dba)2 added is 1 mol% of M2.

[0122] Add 100 mmol of 2-bromonaphthalene, 100 mmol of 4-chlorophenylboric acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF and 200 mL of water to a reaction flask, and add 1 mol% of Pd(PPh3)4. React at 60°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, concentrate the organic phase to obtain a white solid, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain a white powder M5. Wherein, the amount of Pd(PPh3)4 added is 1 mol% of 2-bromonaphthalene.

[0123] Add 100 mmol of M5, 100 mmol of aniline, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of toluene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 100°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M6. Among them, the amount of Pd(dba)2 added is 1 mol% of M5.

[0124] Add 100 mmol of M4, 100 mmol of M6, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder A9. Among them, the amount of Pd(dba)2 added is 1 mol% of M4.

[0125] 1H NMR(400MHz,Chloroform)δ8.22(s,1H),8.13-8.02(m,3H),7.90(d,J=7.2Hz,1H),7.85(d,J=8.4Hz,2H),7.6 8(d,J=7.2Hz,1H),7.65-7.50(m,10H),7.45-7.32(m,9H),7.30-7.16(m,5H),7.12-7.03(m,4H),1.69(s,6H).

[0126] M / Z: Exp., 793.8; Calc., 794.3.

[0127] Synthesis of Compound A10

[0128]

[0129] 100 mmol of 2-bromo-4-chlorophenol, 300 mL of DMF and iodine (100 mmol) were added to the reaction bottle and reacted at 120° C. for 12 h. After the reaction was completed, water was added and solid precipitated, which was filtered to obtain intermediate M1.

[0130] Add 100mmol of M1, 100mmol of 2-fluoro-4-chlorobenzeneboronic acid, 41.4g of potassium carbonate (300mmol), 800mL of THF and 200mL of water to the reaction flask, and add 1mol% of Pd(PPh3)4. React at 60°C for 12h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, concentrate the organic phase to obtain a white solid, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain a white powder M2. Among them, the amount of Pd(PPh3)4 added is 1mol% of M1.

[0131] 100 mmol of M2, 300 mL of DMF, and 41.4 g of potassium carbonate (300 mmol) were added to the reaction flask and reacted at 120° C. for 12 h. After the reaction was completed, water was added, and solid precipitated, which was filtered to obtain intermediate M3.

[0132] Add 100 mmol of M3 and 300 mL of THF to the reaction bottle, cool to 0°C, control the temperature, and drop 100 mmol of cyclopentylmagnesium bromide. After the addition is complete, naturally warm to room temperature. React for 8 hours. After the reaction is complete, add water, solid precipitates, filter, and obtain intermediate M4.

[0133] Add 100mmol of 2-bromo-9,9-dimethylfluorene, 100mmol of 2-amino-9,9-dimethylfluorene, 28.83g of sodium tert-butoxide (300mmol), 800mL of toluene, and add 1mol% of Pd(dba)2 in a reaction flask. React at 100°C for 12h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M5. Among them, the amount of Pd(dba)2 added is 1mol% of 2-bromo-9,9-dimethylfluorene.

[0134] Add 100 mmol of M4, 100 mmol of M5, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M6. Among them, the amount of Pd(dba)2 added is 1 mol% of M4.

[0135] Add 100 mmol of 2-bromonaphthalene, 100 mmol of aniline, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of toluene, and 1 mol% of Pd(dba)2 to a reaction flask. React at 100°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M7. Among them, the amount of Pd(dba)2 added is 1 mol% of 2-bromonaphthalene.

[0136] Add 100 mmol of M6, 100 mmol of M7, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to a reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain a white powder A10. The amount of Pd(dba)2 added is 1 mol% of M6.

[0137] 1H NMR(400MHz,Chloroform)δ8.12(s,1H),8.07(s,1H),7.92(d,J=8.0Hz,2H),7.87(d,J=9.2Hz,2H),7.68(d,J=8.8Hz,2H),7.58-7.5 1(m,6H),7.47-7.30(m,7H),7.29-7.18(m,6H),7.12-7.01(m,4H),3.38(s,1H),2.08-1.98(m,4H),1.76(s,12H),1.74-1.64(m,4H).

[0138] M / Z: Exp., 852.1; Calc., 852.4.

[0139] Synthesis of Compound A13

[0140]

[0141] Add 100mmol of 2-iodo-4-bromophenol, 100mmol of 2-fluoro-4-chlorophenylboronic acid, 41.4g of potassium carbonate (300mmol), 800mL of THF and 200mL of water to a reaction flask, and add 1mol% of Pd(PPh3)4. React at 60°C for 12h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, concentrate the organic phase to obtain a white solid, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain a white powder M1. Among them, the amount of Pd(PPh3)4 added is 1mol% of 2-iodo-4-bromophenol.

[0142] 100 mmol of M1, 300 mL of DMF, and 41.4 g of potassium carbonate (300 mmol) were added to the reaction flask and reacted at 120° C. for 12 h. After the reaction was completed, water was added, and solid precipitated, which was filtered to obtain intermediate M2.

[0143] Add 100 mmol of 3-bromo-9,9-dimethylfluorene, 100 mmol of aniline, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of toluene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 100°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M3. Among them, the amount of Pd(dba)2 added is 1 mol% of 3-bromo-9,9-dimethylfluorene.

[0144] Add 100 mmol of M2, 100 mmol of M3, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M4. Among them, the amount of Pd(dba)2 added is 1 mol% of M2.

[0145] Add 100 mmol of p-chlorobromobenzene, 100 mmol of diphenylamine, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to a reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain a white powder M5. The amount of Pd(dba)2 added is 1 mol% of p-chlorobromobenzene.

[0146] Add 100 mmol of M5, 100 mmol of biboric acid pinacol ester, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M6. Among them, the amount of Pd(dba)2 added is 1 mol% of M5.

[0147] Add 100 mmol of M4, 100 mmol of M6, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF and 200 mL of water to a reaction flask, and add 1 mol% of Pd(PPh3)4. React at 60°C for 12 h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, concentrate the organic phase to obtain a white solid, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain a white powder A13. Among them, the amount of Pd(PPh3)4 added is 1 mol% of M4.

[0148] 1H NMR(400MHz,Chloroform)δ8.21(s,1H),7.97(s,1H),7.90(d,J=7.6Hz,1H),7.76(d,J=9.2Hz,1H),7.70(s,1H),7,61-7.54(m ,5H),7.44(d,J=8.0Hz,1H),7.38-7.30(m,3H),7.29-7.21(m,9H),7.08(d,J=8.0Hz,6H),7.00(t,J=7.6Hz,3H),1.69(s,6H).

[0149] M / Z: Observed, 694.0; Calculated, 694.3.

[0150] Synthesis of Compound A15

[0151]

[0152] Add 100mmol of 2-iodo-4-bromophenol, 100mmol of 2-fluoro-4-chlorophenylboronic acid, 41.4g of potassium carbonate (300mmol), 800mL of THF and 200mL of water to a reaction flask, and add 1mol% of Pd(PPh3)4. React at 60°C for 12h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, concentrate the organic phase to obtain a white solid, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain a white powder M1. Among them, the amount of Pd(PPh3)4 added is 1mol% of 2-iodo-4-bromophenol.

[0153] 100 mmol of M1, 300 mL of DMF, and 41.4 g of potassium carbonate (300 mmol) were added to the reaction flask and reacted at 120° C. for 12 h. After the reaction was completed, water was added, and solid precipitated, which was filtered to obtain intermediate M2.

[0154] Add 100mmol of 2-bromodibenzofuran, 100mmol of 2-amino-9,9-dimethylfluorene, 28.83g of sodium tert-butoxide (300mmol), 800mL of xylene, and 1mol% of Pd(dba)2 to the reaction bottle. React at 120°C for 12h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M3. Among them, the amount of Pd(dba)2 added is 1mol% of 2-bromodibenzofuran.

[0155] Add 100 mmol of M2, 100 mmol of M3, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M4. Among them, the amount of Pd(dba)2 added is 1 mol% of M2.

[0156] Add 100 mmol of 2-bromonaphthalene, 100 mmol of aniline, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of toluene, and 1 mol% of Pd(dba)2 to a reaction flask. React at 100°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M5. The amount of Pd(dba)2 added is 1 mol% of 2-bromonaphthalene.

[0157] Add 100 mmol of M4, 100 mmol of M5, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder A15. Among them, the amount of Pd(dba)2 added is 1 mol% of M3.

[0158] 1 H NMR (400MHz, Chloroform) δ8.21 (s, 2H), 8.03 (s, 1H), 7.99 (d, J = 7.2Hz, 1H), 7.91 (d,J=7.6Hz,1H),7.85(d,J=7.2Hz,1H),7.71(d,J=7.2Hz,1H),7.61(d,J=7.2Hz,1 H),7.60(s,1H),7.55(t,J=7.2Hz,4H),7.50(d,J=7.2Hz,3H),7.42-7.26(m,8H),7 .23(t,J=6.8Hz,4H),7.10(d,J=8.8.0Hz,3H),7.00(t,J=7.2Hz,1H),1.69(s,6H).

[0159] M / Z: Exp., 757.9; Calc., 758.3.

[0160] Synthesis of Compound A18

[0161]

[0162] Add 100mmol of 2-iodo-4-bromophenol, 100mmol of 2-fluoro-4-chlorophenylboronic acid, 41.4g of potassium carbonate (300mmol), 800mL of THF and 200mL of water to a reaction flask, and add 1mol% of Pd(PPh3)4. React at 60°C for 12h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, concentrate the organic phase to obtain a white solid, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain a white powder M1. Among them, the amount of Pd(PPh3)4 added is 1mol% of 2-iodo-4-bromophenol.

[0163] 100 mmol of M1, 300 mL of DMF, and 41.4 g of potassium carbonate (300 mmol) were added to the reaction flask and reacted at 120° C. for 12 h. After the reaction was completed, water was added, and solid precipitated, which was filtered to obtain intermediate M2.

[0164] Add 100 mmol of bromobenzene, 100 mmol of 2-amino (-9,9-spirobifluorene), 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd (dba) 2 to the reaction flask. React at 120 ° C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain a white powder M3. Among them, the amount of Pd (dba) 2 added is 1 mol% of 2-bromobiphenyl.

[0165] Add 100 mmol of M2, 100 mmol of M3, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M4. Among them, the amount of Pd(dba)2 added is 1 mol% of M2.

[0166] Add 100 mmol of 3-bromobiphenyl, 100 mmol of aniline, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to a reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain a white powder M5. Among them, the amount of Pd(dba)2 added is 1 mol% of 3-bromobiphenyl.

[0167] Add 100 mmol of M4, 100 mmol of M5, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder A18. Among them, the amount of Pd(dba)2 added is 1 mol% of M4.

[0168] 1 H NMR(400MHz,Chloroform)δ8.22(d,J=7.6Hz,1H),8.03(d,J=7.6Hz,1H),7.93-7.85(m,4H),7.75 (d,J=8.0Hz,2H),7.68-7.62(m,2H),7.58-7.31(m,10H),7.27-7.12(m,14H),7.10-6.96(m,6H).

[0169] M / Z: Exp., 816.1; Calc., 816.3.

[0170] Synthesis of compound A22

[0171]

[0172] Add 100mmol of 2-iodo-4-bromophenol, 100mmol of 2-fluoro-4-chlorophenylboronic acid, 41.4g of potassium carbonate (300mmol), 800mL of THF and 200mL of water to a reaction flask, and add 1mol% of Pd(PPh3)4. React at 60°C for 12h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, concentrate the organic phase to obtain a white solid, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain a white powder M1. Among them, the amount of Pd(PPh3)4 added is 1mol% of 2-iodo-4-bromophenol.

[0173] 100 mmol of M1, 300 mL of DMF, and 41.4 g of potassium carbonate (300 mmol) were added to the reaction flask and reacted at 120° C. for 12 h. After the reaction was completed, water was added, and solid precipitated, which was filtered to obtain intermediate M2.

[0174] Add 100 mmol of deuterated bromobenzene, 100 mmol of 4-chlorophenylboric acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF and 200 mL of water to the reaction flask, and add 1 mol% of Pd(PPh3)4. React at 60°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactants to room temperature, add water, concentrate the organic phase to obtain a white solid, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain a white powder M3. Among them, the amount of Pd(PPh3)4 added is 1 mol% of deuterated bromobenzene.

[0175] Add 100 mmol of M3, 100 mmol of 2-amino-(9,9-dimethylfluorene), 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M4. Among them, the amount of Pd(dba)2 added is 1 mol% of M3.

[0176] Add 100 mmol of M2, 100 mmol of M4, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M5. Among them, the amount of Pd(dba)2 added is 1 mol% of M2.

[0177] Add 100 mmol of 2-bromonaphthalene, 100 mmol of aniline, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of toluene, and 1 mol% of Pd(dba)2 to a reaction flask. React at 100°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M6. Wherein, the amount of Pd(dba)2 added is 1 mol% of 2-bromonaphthalene.

[0178] Add 100 mmol of M5, 100 mmol of M6, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder A22. Among them, the amount of Pd(dba)2 added is 1 mol% of M5.

[0179] 1 H NMR (400MHz, Chloroform) δ8.22(s,1H),8.04(s,1H),7.95(d,J=6.8Hz,1H),7.86(d,J=8.8Hz,1H),7.71(d,J=7.2Hz,1 H),7.62(d,J=6.8Hz,1H),7.55(d,J=7.6Hz,6H),7.48-7.31(m,8H),7.27-7.20(m,5H),7.13-6.96(m,4H),1.69(s,6H).

[0180] M / Z: Exp., 739.2; Calc., 739.3.

[0181] Synthesis of Compound A24

[0182]

[0183] 100 mmol of 2-bromo-4-chlorophenol, 300 mL of DMF and iodine (100 mmol) were added to the reaction bottle and reacted at 120° C. for 12 h. After the reaction was completed, water was added and solid precipitated, which was filtered to obtain intermediate M1.

[0184] Add 100mmol of M1, 100mmol of 2-fluoro-4-chlorobenzeneboronic acid, 41.4g of potassium carbonate (300mmol), 800mL of THF and 200mL of water to the reaction flask, and add 1mol% of Pd(PPh3)4. React at 60°C for 12h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, concentrate the organic phase to obtain a white solid, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain a white powder M2. Among them, the amount of Pd(PPh3)4 added is 1mol% of M1.

[0185] 100 mmol of M2, 300 mL of DMF, and 41.4 g of potassium carbonate (300 mmol) were added to the reaction flask and reacted at 120° C. for 12 h. After the reaction was completed, water was added, and solid precipitated, which was filtered to obtain intermediate M3.

[0186] Add 100mmol of M3, 100mmol of dibenzothiophene-3-boric acid, 41.4g of potassium carbonate (300mmol), 800mL of THF and 200mL of water to the reaction flask, and add 1mol% of Pd(PPh3)4. React at 60°C for 12h. After the reaction is completed, stop the reaction, cool the reactants to room temperature, add water, concentrate the organic phase to obtain a white solid, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain a white powder M4. Among them, the amount of Pd(PPh3)4 added is 1mol% of M3.

[0187] Add 100 mmol of 2-bromonaphthalene, 100 mmol of 2-amino-9,9-dimethylfluorene, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of toluene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 100°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M5. Among them, the amount of Pd(dba)2 added is 1 mol% of 2-bromonaphthalene.

[0188] Add 100 mmol of M4, 100 mmol of M5, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M6. Among them, the amount of Pd(dba)2 added is 1 mol% of M4.

[0189] Add 100 mmol of M6, 100 mmol of diphenylamine, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder A24. Among them, the amount of Pd(dba)2 added is 1 mol% of M6.

[0190] 1H NMR (400MHz, Chloroform) δ8.47(s,1H),8.44(d,J=7.6Hz,1H),8.28(d,J=8.4Hz,2H),8.16(d,J=6.8Hz,1H),8.03(s,1H),7.95(d,J=7.2Hz, 1H),7.90(d,J=7.2Hz,1H),7.86(d,J=7.6Hz,2H),7.75-7.51(m,7H),7.49-7.34(m,5H),7.31-7.17(m,7H),7.11-6.98(m,7H),1.69(s,6H).

[0191] M / Z: Exp., 850.2; Calc., 850.3.

[0192] Synthesis of Compound A28

[0193]

[0194] Add 100mmol of 2-bromo-1,5-dichloro-3-fluorobenzene and 300mL of THF to the reaction bottle, cool to -78°C, control the temperature, add 110mmol of n-butyl lithium dropwise, control the temperature for 1h, maintain the temperature, add 110mmol of tributyl borate dropwise, naturally warm to room temperature, and react for 8h. After the reaction is completed, add water, solid precipitates, filter, and obtain intermediate M1.

[0195] Add 100mmol of 2-iodo-4-bromophenol, 100mmol of M1, 41.4g of potassium carbonate (300mmol), 800mL of THF and 200mL of water to a reaction flask, and add 1mol% of Pd(PPh3)4. React at 60°C for 12h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, concentrate the organic phase to obtain a white solid, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain a white powder M2. Among them, the amount of Pd(PPh3)4 added is 1mol% of 2-iodo-4-bromophenol.

[0196] 100 mmol of M2, 300 mL of DMF, and 41.4 g of potassium carbonate (300 mmol) were added to the reaction flask and reacted at 120° C. for 12 h. After the reaction was completed, water was added, and solid precipitated, which was filtered to obtain intermediate M3.

[0197] Add 100 mmol of 3-bromobiphenyl, 100 mmol of 2-amino (-9,9-spirobifluorene), 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd (dba) 2 to the reaction flask. React at 120 ° C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain a white powder M4. Among them, the amount of Pd (dba) 2 added is 1 mol% of 3-bromobiphenyl.

[0198] Add 100 mmol of M3, 100 mmol of M4, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M5. Among them, the amount of Pd(dba)2 added is 1 mol% of M3.

[0199] Add 100 mmol of 3,5-dimethylbromobenzene, 100 mmol of aniline, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M6. Among them, the amount of Pd(dba)2 added is 1 mol% of aniline.

[0200] Add 100 mmol of M5, 100 mmol of M6, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M7. Among them, the amount of Pd(dba)2 added is 1 mol% of M5.

[0201] Add 100 mmol of M7, 100 mmol of dibenzofuran-3-boric acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of DMF and 200 mL of water to a reaction flask, and add 1 mol% of Pd(PPh3)4. React at 100°C for 12 h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, concentrate the organic phase to obtain a white solid, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain a white powder A28. Among them, the amount of Pd(PPh3)4 added is 1 mol% of M7.

[0202] 1 H NMR(400MHz,Chloroform)δ9.21(s,1H),8.21(d,J=7.2Hz,2H),8.13(s,1H),7.98(d,J=7.2Hz,1H),7.93-7.85(m,4H),7.80-7.67(m,5H) ,7.63-7.55(m,4H),7.52-7.30(m,8H),7.28-7.10(m,13H),7.08(d,J=8.0Hz,2H),7.03-6.95(m,2H),5.99(d,J=7.2Hz,1H),2.28(s,6H).

[0203] M / Z: Exp., 1010.1; Calc., 1010.4.

[0204] Synthesis of Compound A29

[0205]

[0206] Add 100mmol of 5-chloro-2-hydroxyphenylboronic acid, 100mmol of 2-bromo-1-fluoronaphthalene, 41.4g of potassium carbonate (300mmol), 800mL of THF and 200mL of water to a reaction flask, and add 1mol% of Pd(PPh3)4. React at 120°C for 12h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, concentrate the organic phase to obtain a white solid, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain a white powder M1. Among them, the amount of Pd(PPh3)4 added is 1mol% of 5-chloro-2-hydroxyphenylboronic acid.

[0207] 100 mmol of M1, 300 mL of DMF, and 41.4 g of potassium carbonate (300 mmol) were added to the reaction flask and reacted at 120° C. for 12 h. After the reaction was completed, water was added, and solid precipitated, which was filtered to obtain intermediate M2.

[0208] Add 100 mmol of 2-bromonaphthalene, 100 mmol of 2-amino-(9,9-dimethylfluorene), 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M3. Among them, the amount of Pd(dba)2 added is 1 mol% of 2-bromonaphthalene.

[0209] Add 100 mmol of M2, 100 mmol of M3, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder M4. Among them, the amount of Pd(dba)2 added is 1 mol% of M2.

[0210] Add 100 mmol of M4 and 300 mL of DMF to the reaction flask, add N-bromosuccinimide (NBS) (100 mmol) in batches, and react at 60° C. for 12 h. After the reaction is completed, add water, solid precipitates, and filter to obtain intermediate M5.

[0211] Add 100 mmol of M5, 100 mmol of N-phenyl-4-benzidine, 28.83 g of sodium tert-butoxide (300 mmol), 800 mL of xylene, and 1 mol% of Pd(dba)2 to the reaction flask. React at 120°C for 12 hours. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and purify the obtained solid by recrystallization with toluene to obtain white powder A29. Among them, the amount of Pd(dba)2 added is 1 mol% of M5.

[0212] 1 H NMR (400MHz, Chloroform) δ8.95(d,J=7.6Hz,1H),8.22(s,1H),8.12(d,J=6.8Hz,1H),8.03(s,1H),7.88(d,J=7.2Hz,1H),7.84( d,J=8.0Hz,1H),7.75(t,J=7.6Hz,3H),7.64-7.52(m,9H),7.52-7.31(m,9H),7.30-7.19(m,5H),7.15-6.95(m,4H),1.69(s,6H).

[0213] M / Z: Exp., 794.2; Calc., 794.3.

[0214] Other compounds of the present application can be synthesized by selecting suitable raw materials according to the ideas of the above synthesis examples, or by selecting any other suitable methods and raw materials for synthesis.

[0215] Example 1

[0216] A glass substrate with an anode was obtained by ultrasonically treating a glass plate coated with a 150 nm thick ITO transparent conductive layer in a commercial cleaning agent, rinsing in deionized water, ultrasonically degreasing in an acetone-ethanol mixed solvent, baking in a clean environment until the water was completely removed, cleaning with ultraviolet light and ozone, and bombarding the surface with a low-energy cation beam;

[0217] Then, the glass substrate with the anode is placed in a vacuum chamber and evacuated to less than 10 -5 A hole injection layer is vacuum-deposited on the anode layer film of the above-mentioned glass substrate with an anode. The hole injection layer includes hole injection layer material HT-1 and p-type dopant p-1. The evaporation is performed by multi-source co-evaporation. The evaporation rate of the hole injection layer material HT-1 is adjusted to 0.1 nm / s, the ratio of the evaporation rate of the p-type dopant p-1 to the evaporation rate of the hole injection layer material HT-14 is 2:98, the total evaporation film thickness is 10 nm, and the hole injection layer material HT-1 and the p-type dopant p-1 are as follows:

[0218]

[0219] Then, a hole transport layer material A1 is vacuum-deposited on the hole injection layer as a hole transport layer. The deposition rate is 0.1 nm / s and the deposition film thickness is 80 nm. The hole transport layer material A1 is as follows:

[0220]

[0221] Then, a light-emitting layer is vacuum-deposited on the hole transport layer. The light-emitting layer includes a light-emitting layer main material GPH and a light-emitting layer guest material RPD. The light-emitting layer is evaporated by a multi-source co-evaporation method. The evaporation rate of the light-emitting layer main material GPH is adjusted to 0.1 nm / s, and the evaporation rate of the light-emitting layer guest material RPD is 3% of the evaporation rate of the light-emitting layer main material GPH. The total film thickness of the evaporation is 30 nm. The light-emitting layer main material GPH and the light-emitting layer guest material RPD are as follows:

[0222]

[0223] Then, an electron transport layer is vacuum evaporated on the light-emitting layer, and material ET is selected as the electron transport material. The evaporation rate is 0.1nm / s, the evaporation film thickness is 30nm, and the electron transport material ET is as follows:

[0224]

[0225] Then, LiF with a thickness of 10 nm was vacuum-deposited on the electron transport layer as an electron injection layer, wherein the evaporation rate was 0.1 nm / s;

[0226] Finally, an Al layer with a thickness of 150 nm was vacuum evaporated on the electron injection layer as a cathode of the organic electroluminescent device, wherein the evaporation rate was 0.1 nm / s.

[0227] Example 2-12

[0228] Except that the hole transport layer materials are replaced by A4, A6, A9, A10, A13, A15, A18, A22, A24, A28, and A29 respectively instead of A1, the rest is the same as Example 1.

[0229] Comparative Example 1

[0230] Except that HT-2 is used as the hole transport layer material instead of A1, the rest is the same as Example 1.

[0231]

[0232] Comparative Example 2

[0233] Except that the hole transport layer material is R instead of A1, the rest is the same as Example 1.

[0234]

[0235] The organic electroluminescent device prepared by the above process was subjected to the following performance tests:

[0236] At the same brightness, the driving voltage, current efficiency and device life of the organic electroluminescent devices prepared in Examples 1-12 and Comparative Examples 1-2 were measured using a digital source meter and a brightness meter. Specifically, the voltage was increased at a rate of 0.1 V per second, and the brightness of the organic electroluminescent device was measured when it reached 5000 cd / m 2 The voltage at which the light is reflected is the driving voltage, and the current density at this time is measured at the same time; the ratio of brightness to current density is the current efficiency; the life test of LT95 is as follows: use a brightness meter at 5000cd / m 2 At the same brightness, the current is kept constant and the brightness of the organic electroluminescent device is measured to drop to 4750cd / m 2 The time is in hours. The results are shown in Table 1.

[0237] Table 1 Performance results of organic electroluminescent devices

[0238]

[0239]

[0240] As can be seen from Table 1, the organic electroluminescent devices prepared in Examples 1-12 use compounds A1, A4, A6, A9, A10, A13, A15, A18, A22, A24, A28, and A29 provided in this application as hole transport layer materials. Compared with Comparative Examples 1-2 using known materials in the prior art as hole transport layer materials for organic electroluminescent devices, the organic electroluminescent devices of this application present lower driving voltages, higher current efficiency, and longer LT95 lifespans. Thus, it is shown that the application uses the compound of formula (I) as a hole transport layer material for organic electroluminescent devices, which can effectively reduce driving voltages, improve current efficiency, and extend device service life. The materials of this application have significant performance improvements, especially in terms of improving the efficiency of organic electroluminescent devices and extending the life of organic electroluminescent devices, and can obtain organic electroluminescent devices with good performance.

[0241] The above description is only a preferred embodiment of the present application and is not intended to limit the protection scope of the present application. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present application are included in the protection scope of the present application.

Claims

1. An organic electroluminescent device, wherein: The organic electroluminescent device comprises a hole transport layer, and the hole transport layer material comprises a compound of formula (I): in, Ar 1 and Ar 2 Each independently selected from C6-C 30 Aryl; R 1 -R 5 are each independently selected from hydrogen, deuterium, C1-C6 alkyl, C1-C6 alkenyl, C6-C6 unsubstituted or substituted by Rc 30 Aryl, unsubstituted or Rc-substituted C3-C 30 heteroaryl, and the adjacent R 1 -R 5 They can be connected to form a ring; R 6 and R 7 Each independently selected from hydrogen, deuterium, C1-C6 alkyl, C5-C 20 Cycloalkyl, C1-C6 alkenyl, unsubstituted or Rc-substituted C6-C 30 Aryl, unsubstituted or Rc-substituted C3-C 30 heteroaryl, and R 6 and R 7 They can be connected to form a ring; R 8 and R 9 are each independently selected from hydrogen, deuterium, C1-C6 alkyl, C1-C6 alkenyl, C6-C6 unsubstituted or substituted by Rc 30 Aryl, unsubstituted or Rc-substituted C3-C 30 heteroaryl, and R 8 and R 9 They can be connected to form a ring; R' and R" are each independently selected from C1-C6 alkyl, C5-C 20 Cycloalkyl, unsubstituted or substituted by Rc C6-C 30 Aryl, unsubstituted or Rc-substituted C3-C 30 Heteroaryl, and R' and R" may be connected to form a ring; L 1 and L 2 Each independently selected from a chemical bond, a C6-C 30 arylene; R a ', R b ', R c ', R d 'are each independently selected from hydrogen, deuterium, C1-C6 alkyl, C1-C6 alkenyl, C6-C6 unsubstituted or substituted by Rc 30 Aryl, and the adjacent R a ', R b ', R c ', R d ' can be connected to form a ring; The heteroatoms on the heteroaryl group are each independently selected from O, S or N; The substituents Rc of each group are each independently selected from deuterium, halogen, C1-C4 alkyl, phenyl, biphenyl, terphenyl, pyridyl, pyrimidyl or naphthyl.

2. The organic electroluminescent device according to claim 1, wherein: Ar 1 and Ar 2 Each independently selected from C6-C 18 Aryl; and / or R 1 -R 5 are each independently selected from hydrogen, deuterium, C1-C6 alkyl, C1-C6 alkenyl, C6-C6 unsubstituted or substituted by Rc 18 Aryl, unsubstituted or Rc-substituted C3-C 18 heteroaryl, and the adjacent R 1 -R 5 can be connected to form a ring; and / or, R 6 and R 7 Each independently selected from hydrogen, deuterium, C1-C6 alkyl, C5-C 20 Cycloalkyl, C1-C6 alkenyl, unsubstituted or Rc-substituted C6-C 18 Aryl, unsubstituted or Rc-substituted C3-C 18 heteroaryl, and R 6 and R 7 can be connected to form a ring; and / or, R 8 and R 9 are each independently selected from hydrogen, deuterium, C1-C6 alkyl, C1-C6 alkenyl, C6-C6 unsubstituted or substituted by Rc 18 Aryl, unsubstituted or Rc-substituted C3-C 18 heteroaryl, and R 8 and R 9 can be connected to form a ring; and / or, R' and R" are each independently selected from C1-C6 alkyl, C5-C 10 Cycloalkyl, unsubstituted or substituted by Rc C6-C 18 Aryl, unsubstituted or Rc-substituted C3-C 18 Heteroaryl, and R' and R" may be connected to form a ring; and / or, L 1 and L 2 Each independently selected from a chemical bond, a C6-C 18 arylene; and / or, R a ', R b ', R c ', R d 'are each independently selected from hydrogen, deuterium, C1-C6 alkyl, C1-C6 alkenyl, C6-C6 unsubstituted or substituted by Rc 18 Aryl, and adjacent R a ', R b ', R c ', R d ' can be connected to form a ring.

3. The organic electroluminescent device according to claim 1, wherein: Ar 1 and Ar 2 A group each independently selected from the following compounds which are unsubstituted or substituted with Rc: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, 9,9-dimethylfluorene, spirofluorene; and / or, R 1 -R 5 Each independently selected from hydrogen, deuterium, methyl, ethyl, propyl, vinyl, propenyl, butenyl, a group of the following compounds which are unsubstituted or substituted with Rc: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, anthracene, dibenzofuran, dibenzothiophene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, spirofluorene, and the adjacent R 1 -R 5 can be connected to form a ring; and / or, R 6 and R 7 each independently selected from hydrogen, deuterium, methyl, ethyl, propyl, cyclopentyl, cyclohexyl, vinyl, propenyl, butenyl, a group of the following compounds which are unsubstituted or substituted with Rc: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, pyridine, benzofuran, dibenzofuran, aza-dibenzofuran, benzothiophene, dibenzothiophene, aza-dibenzothiophene, 9,9-dimethylfluorene, spirofluorene, aromatic amine, carbazole, and R 6 and R 7 can be connected to form a ring; and / or, R 8 and R 9 each independently selected from hydrogen, deuterium, methyl, ethyl, propyl, vinyl, propenyl, butenyl, a group of the following compounds which are unsubstituted or substituted with Rc: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, pyridine, benzofuran, dibenzofuran, aza-dibenzofuran, benzothiophene, dibenzothiophene, aza-dibenzothiophene, 9,9-dimethylfluorene, spirofluorene, aromatic amine, carbazole, and R 8 and R 9 can be connected to form a ring; and / or, R' and R" are each independently selected from methyl, ethyl, propyl, cyclopentyl, cyclohexyl, a group of the following compounds which are unsubstituted or substituted by Rc: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, dibenzofuran, benzothiophene, dibenzothiophene, 9,9-dimethylfluorene, spirofluorene, aromatic amine, carbazole, and R' and R" may be connected to form a ring; and / or, L 1 and L 2 Each of the subunits independently selected from the following compounds which are chemically bonded, unsubstituted or substituted by Rc: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, 9,9-dimethylfluorene, spirofluorene, aromatic amine, carbazole; and / or, R a ', R b ', R c ', R d 'are each independently selected from hydrogen, deuterium, methyl, ethyl, propyl, vinyl, propenyl, butenyl, a group of the following compounds which are unsubstituted or substituted with Rc: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, 9,9-dimethylfluorene, spirofluorene, and the adjacent R a ', R b ', R c ', R d ' can be connected to form a ring.

4. The organic electroluminescent device according to claim 1, wherein: The thickness of the hole transport layer is 60nm-100nm.

5. The organic electroluminescent device according to claim 1, wherein: The compound of formula (I) is selected from the following compounds A1 to A30:

6. A display device comprising the organic electroluminescent device according to any one of claims 1 to 5.

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