Compound, charge generation layer material, organic electroluminescent device and display device

Abstract

The invention relates to the technical field of organic light-emitting display, in particular to a compound, a charge generation layer material, an organic light-emitting device and a display device. The compound provided by the invention is shown as a formula (I). The organic light-emitting device provided by the invention comprises the charge generation layer, and the material of the charge generation layer comprises the compound shown in the formula (I), has efficient charge generation capability, can effectively improve the light-emitting efficiency of the organic light-emitting device, has a relatively shallow energy level, and can be better matched with the material of the adjacent layer for use, so that the light-emitting efficiency of the organic light-emitting device is improved. The charge transmission 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.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of organic light-emitting display, in particular to a compound, a charge generation layer material, an organic electroluminescent device and a display device. BACKGROUND

[0002] Electroluminescence (EL) refers to a phenomenon that a luminescent material emits light under the action of an electric field, which is a process of directly converting electric energy into light energy. An organic electroluminescent display (hereinafter referred to as OLED) has a series of advantages such as self-luminescence, low-voltage direct current driving, full solidification, wide viewing angle, light weight, simple composition and process, etc. Compared with liquid crystal displays, the organic electroluminescent display does not need a backlight source, has a large viewing angle and low power consumption, and the response speed can reach 1000 times of that of a liquid crystal display, and the manufacturing cost is lower than that of a liquid crystal display with the same resolution. Therefore, the organic electroluminescent device has a very broad application prospect.

[0003] With the continuous advancement of OLED technology in the fields of lighting and display, people pay more attention to the research on high-efficiency organic materials affecting the performance of OLED devices. An organic electroluminescent device with high efficiency and long service life is usually the result of optimization of the device structure and various organic materials, which provides great opportunities and challenges for chemists to design and develop functional materials with various structures. The stacked device can effectively improve the service life of the device, and thus has been a research hotspot in recent years. How to develop a high-efficiency charge generation layer material and select a matching light-emitting unit to improve the luminous efficiency of the organic electroluminescent device and prolong its service life is a technical problem to be solved by those skilled in the art. SUMMARY

[0004] The present application aims to provide a compound, a charge generation layer material, an organic electroluminescent device and a display device to improve the luminous efficiency of the organic electroluminescent device and prolong its service life.

[0005] The first aspect of the present application aims to provide a compound having a structure shown in formula (I):

[0006]

[0007] L 1 , L 2 , L 3 are each independently selected from a chemical bond, an unsubstituted or Rc-substituted C6-C 30 arylene, an unsubstituted or Rc-substituted C3-C 30 heteroarylene;

[0008] A is selected from C that is either unsubstituted or substituted by Rc. 10 -C 30 Aromatic group, unsubstituted or Rc-substituted C9-C 30 Mixed aromatics;

[0009] B is selected from the following structure:

[0010]

[0011] R1-R7 are each independently selected from C1-C4 alkanes, unsubstituted or Rc-substituted C6-C alkanes. 18 Aromatic group, unsubstituted or Rc-substituted C3-C 18 Mixed aromatics;

[0012] The heteroatoms on the heteroaryl or heteroalkylene group are each independently selected from O, S, or N;

[0013] Rc is independently selected from hydrogen, deuterium, halogen, nitro, cyano, C1-C4 alkyl, phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl, or naphthyl.

[0014] Preferably, R1-R7 are each independently selected from groups of the following compounds: methyl, ethyl, isopropyl, tert-butyl, unsubstituted or Rc-substituted: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, dibenzofuran, dibenzothiophene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, and spirofluorene.

[0015] Preferably, L 1 L 2 L 3 The groups are independently selected from the following compounds that are chemically bonded, unsubstituted, or Rc-substituted: phenyl, pyridinyl, pyrimidinyl, quinoxalinyl, quinazolinyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, fluorenyl, anthraceneyl, dibenzofuranyl, dibenzothiopheneyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, and spirofluorenyl.

[0016] Preferably, A is selected from the following structures:

[0017]

[0018] Preferably, the compound of formula (I) is selected from the compounds shown in A1 to A40:

[0019]

[0020]

[0021] A second objective of this invention is to provide a charge-generating layer material, comprising at least one of the aforementioned compounds.

[0022] Preferably, the charge generation layer material further comprises Li or Yb, and the mass percentage of the Li or Yb in the charge generation layer material is 0.5%-2.5%.

[0023] A third object of the present application is to provide an organic electroluminescent device comprising a charge generation layer and an electron transport layer, wherein the charge generation layer comprises at least one of the above-mentioned charge generation layer materials.

[0024] Preferably, the thickness of the charge generation layer is 10-30 nm, and the thickness of the electron transport layer is 10-40 nm.

[0025] A fourth object of the present application is to provide a display device comprising the above-mentioned organic electroluminescent device.

[0026] Compared with the prior art, the present application has the following technical effects:

[0027] The organic electroluminescent device provided by the present application has a charge generation layer material which is a heteroatom (P, Ge, As) substituted phenanthroline compound. The introduction of the heteroatom fragment can enhance the thermal stability of the material and improve the service life. Meanwhile, the introduction of the bulky fused ring structure can improve the charge transport capacity of the material. The material of the present application has high charge generation capacity, which can effectively improve the luminous efficiency of the organic electroluminescent device. Meanwhile, the material has a relatively shallow energy level, which can be used in combination with the material of the adjacent layer to effectively improve the charge transport performance of the organic electroluminescent device, improve the luminous efficiency of the organic electroluminescent device, reduce the driving voltage thereof and prolong the service life thereof. The display device provided by the present application has excellent display effect. BRIEF DESCRIPTION OF DRAWINGS

[0028] Figure 1 Fig. 1 is a schematic structural diagram of a typical organic electroluminescent device 20;

[0029] Fig. 1 is a schematic structural diagram of a typical organic electroluminescent device 20; DETAILED DESCRIPTION

[0030] The advantages and features of the present application will become apparent from specific examples which are given as particular embodiments of the present application and which are indicative of the various embodiments of which the principle of the present application can be employed. The number of embodiments of the present application is not limited to the particular examples described. Although the present application will be described with reference to the preferred embodiments illustrated in the drawings, various modifications and changes can be suggested to one skilled in the art, and it is understood that the present application extends to include such modifications and changes. In order to provide a comprehensive understanding of the present application, specific details have been set forth in the following description. The present application can be practiced without these specific details. In addition, well-known or conventional elements have been omitted or simplified in order not to obscure the present application with unnecessary detail. For the purpose of clarity, technical lingo has been defined in the description of the embodiments. Embodiments of the present application and features in embodiments of the present application can be combined with each other if not in conflict.

[0031] In the present application, there is no particular limitation on the kind and structure of the organic electroluminescent device, and it can be any of the different kinds and structures of organic electroluminescent devices known in the art, as long as at least one of the charge generation layer materials provided by the present application can be used.

[0032] In one embodiment of the present application, the organic electroluminescent device includes an anode and a cathode, a number of m light-emitting units and a number of (m-1) charge generation layers stacked between the anode and the cathode, the charge generation layers being between two adjacent light-emitting units, each of the charge generation layers including an n-type charge generation layer and a p-type charge generation layer, wherein m is an integer ≥ 2; each of the light-emitting units includes at least one light-emitting layer, the maximum emission wavelength of the light emitted in different light-emitting units being different; at least one of the n-type charge generation layers includes at least one compound represented by formula (I) and a material containing metal Li or Yb.

[0033] In one embodiment of the present application, the light-emitting unit in the organic electroluminescent device can include a first light-emitting unit and a second light-emitting unit, the two light-emitting units can be the same or different; the charge generation layer can be disposed between the first light-emitting unit and the second light-emitting unit, the first light-emitting unit can be disposed between the reflective anode and the charge generation layer, the second light-emitting unit can be disposed between the charge generation layer and the cathode electrode, and the n-type charge generation layer of the charge generation layer can include at least one compound represented by formula (I) and a material containing metal.

[0034] In other embodiments of the present application, the organic electroluminescent device of the present application can be a light-emitting device of a top-emitting structure, and can sequentially include a reflective anode, a first light-emitting unit, a charge generation layer, a second light-emitting unit, an electron injection layer, and a transparent or semi-transparent cathode electrode on a substrate.

[0035] The organic electroluminescent device of the present application can also be a light-emitting device of a bottom emission structure, and can sequentially include a transparent or semi-transparent reflective anode, a first light-emitting unit, a charge generation layer, a second light-emitting unit, an electron injection layer, and a cathode electrode on a substrate.

[0036] The organic electroluminescent device of the present application can also be a light-emitting device of a double-sided emission structure, and can sequentially include a transparent or semi-transparent reflective anode, a first light-emitting unit, a charge generation layer, a second light-emitting unit, an electron injection layer, and a transparent or semi-transparent cathode electrode on a substrate.

[0037] Each of the above-described organic electroluminescent devices can include a first light-emitting unit including a first hole injection layer, a first hole transport layer, a first light-emitting layer, and a first electron transport layer, which are sequentially disposed, and a second light-emitting unit including a second hole injection layer, a second hole transport layer, a second light-emitting layer, and a second electron transport layer, which are sequentially disposed.

[0038] In addition, the organic electroluminescent device of the present application can 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, and a light extraction layer on the transparent electrode on the light emission side.

[0039] However, the structure of the organic electroluminescent device of the present application is not limited to the above-described specific structure, and if necessary, each of the above-described layers can be omitted or added. The thickness of the above-described reflective anode, hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron injection layer, cathode, and light extraction layer is not particularly limited, as long as the object of the present application can be achieved. For example, the organic electroluminescent device can sequentially include a reflective anode (100 nm to 150 nm) made of a metal, a first hole injection layer (5 nm to 20 nm), a first hole transport layer (80 nm to 140 nm), an electron blocking layer (5 nm to 20 nm), a first light-emitting layer (15 nm to 40 nm), a hole blocking layer (5 nm to 20 nm), a first electron transport layer (10 nm to 40 nm), a charge generation layer (10 nm to 30 nm), a second hole injection layer (5 nm to 20 nm), a second hole transport layer (80 nm to 140 nm), a second light-emitting layer (15 nm to 40 nm), a second electron transport layer (10 nm to 40 nm), an electron injection layer (5 nm to 20 nm), a transparent or semi-transparent cathode electrode, and a light extraction layer (50 nm to 90 nm) on a substrate. Exemplarily, Figure 1A schematic diagram of a typical organic electroluminescent device 20 is shown, in which, from bottom to top, a substrate 21, a reflective anode 22, a first hole injection layer 231, a first hole transport layer 241, a first light emitting layer 251, a first electron transport layer 261, a charge generation layer 27, a second hole injection layer 232, a second hole transport layer 242, a second light emitting layer 252, a second electron transport layer 262, an electron injection layer 28, and a cathode electrode 29 are sequentially arranged. It can be understood that Figure 1 The structure of a typical organic electroluminescent device is only schematically shown, and the present application is not limited to this structure. The charge generation layer material of the present application can be used in any type of organic electroluminescent device.

[0040] For the sake of convenience, the organic electroluminescent device of the present application is described below, but this does not mean any limitation on the scope of protection of the present application. It can be understood that all organic electroluminescent devices using the charge generation layer material of the present application are within the scope of protection of the present application.

[0041] In the present application, the substrate 21 is not particularly limited, and conventional substrates used in organic electroluminescent devices in the prior art can be used, for example, glass, polymeric materials, and glass and polymeric materials with thin film transistor (TFT) components, etc.

[0042] In the present application, the material of the reflective anode 22 is not particularly limited, and can be selected from transparent conductive materials known in the prior art, such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), etc., can also be selected from metal materials such as silver and its alloys, aluminum and its alloys, etc., or can also be selected from organic conductive materials such as poly 3,4-ethylenedioxythiophene (PEDOT), or the reflective anode 22 is a multilayer structure formed by the above-mentioned materials, and the present application does not particularly limit the number of layers of the multilayer structure, which can be selected according to actual needs, as long as the purpose of the present application can be achieved, for example, 1 layer, 2 layers, 3 layers or more.

[0043] In the present application, the materials of the first hole injection layer 231 and the second hole injection layer 232 are not particularly limited, and can be made of hole injection layer materials known in the art or made of hole transport layer materials (HTM) known in the art. For example, at least one of the known hole transport layer materials (HTM) is selected as the hole injection layer material.

[0044] In the present application, the first hole injection layer 231 and the second hole injection layer 232 can also include a p-type dopant, and the present application does not particularly limit the type of p-type dopant, and various p-type dopants known in the art can be used. For example, the p-type dopant can be selected from, but not limited to, at least one of the following p-1 to p-3 compounds:

[0045]

[0046] In the present application, the amount of p-type dopant is not particularly limited and can be an amount known to those skilled in the art.

[0047] In the present application, the materials of the first hole transport layer 241 and the second hole transport layer 242 are not particularly limited and can be made of hole transport materials (HTMs) known in the art. The present application does not particularly limit the number of hole transport layers and can be adjusted as needed, as long as the purpose of the present application is met, for example, 1 layer, 2 layers, 3 layers, 4 layers, or more.

[0048] For example, the HTM for the hole injection layer material and the HTM for the hole transport layer material can be selected from, but not limited to, at least one of the following HT-1 to HT-31 compounds:

[0049]

[0050]

[0051] In the present application, the materials of the first light emitting layer 251 and the second light emitting layer 252 are not particularly limited and can each 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 can be an amount known to those skilled in the art.

[0052] In the present application, the light emitting layer can include a blue light emitting layer, a green light emitting layer, or a red light emitting layer, and the light emitting material in the light emitting layer is not particularly limited and various light emitting materials known to those skilled in the art can be used.

[0053] In the present application, the light emitting layer host material is not particularly limited and at least one of the light emitting layer host materials known in the art can be used. For example, it can be selected from, but not limited to, at least one of the following BH-1 to BH-10 compounds:

[0054]

[0055] In the present application, the light emitting layer guest material is not particularly limited and at least one of the light emitting layer guest materials known in the art can be used. For example, the light emitting layer guest material can be selected from, but not limited to, at least one of the following BD-1 to BD-9 compounds:

[0056]

[0057] In the present application, the first electron transport layer 261 and the second electron transport layer 262 described above contain at least one of known electron transport layer materials, and can also contain a combination of different electron transport layer materials. The number of layers of the electron transport layer is not particularly limited and can be adjusted as needed, as long as the purpose of the present application is met, for example, 1 layer, 2 layers, 3 layers, 4 layers, or more layers.

[0058] For example, the known electron transport layer material can be selected from, but not limited to, at least one of the following ET-1 to ET-57 compounds:

[0059]

[0060]

[0061]

[0062] In the present application, the first electron transport layer 261 and the second electron transport layer 262 can each include an n-type dopant, and the type of n-type dopant is not particularly limited and various n-type dopants known in the art can be used, for example, the following n-type dopant (8-hydroxyquinoline lithium (LiQ)) can be used:

[0063]

[0064] In the present application, the amount of n-type dopant is not particularly limited and can be an amount known to those skilled in the art.

[0065] In the present application, the charge generation layer 27 can contain at least one of the charge generation layer materials of the present application, and can also contain a combination of at least one of the charge generation layer materials of the present application and at least one of known charge generation materials.

[0066] For example, the known charge generation material can be selected from, but not limited to, at least one of the following CGL00R1 to CGL00R5 compounds:

[0067]

[0068] In the present application, the material of the electron injection layer 28 described above is not particularly limited and known electron injection layer materials in the art can be used, for example, at least one of the materials such as 8-hydroxyquinoline lithium (LiQ), LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, etc. in the prior art can be included, but not limited thereto.

[0069] In the present application, the material of the cathode electrode 29 is not particularly limited and can be selected from, but not limited to, a magnesium-silver mixture, LiF / Al, ITO, Al, etc. metals, metal mixtures, oxides, etc.

[0070] The method for preparing the organic electroluminescent device of the present application is not particularly limited and any method known in the art can be used, for example, the present application can be prepared using the following preparation method:

[0071] (1) cleaning the reflective anode 22 on the top-emitting organic electroluminescent device substrate 21, respectively through the steps of pickling, water washing, brushing, high-pressure water washing, air knife, etc. in a cleaning machine, and then heating treatment;

[0072] (2) vacuum evaporating a hole injection material as a first hole injection layer 231 on the reflective anode 22;

[0073] (3) vacuum evaporating a hole transport layer material as a first hole transport layer 241 on the first hole injection layer 231;

[0074] (4) vacuum evaporating a first light-emitting layer 251 on the first hole transport layer 241, the light-emitting layer containing a light-emitting layer host material and a light-emitting layer guest material;

[0075] (5) vacuum evaporating an electron transport material as a first electron transport layer 261 on the first light-emitting layer 251;

[0076] (6) vacuum evaporating a charge generation material as a charge generation layer 27 on the first electron transport layer 261;

[0077] (7) vacuum evaporating a hole injection material as a second hole injection layer 232 on the charge generation layer 27;

[0078] (8) vacuum evaporating a hole transport layer material as a second hole transport layer 242 on the second hole injection layer 232;

[0079] (9) vacuum evaporating a second light-emitting layer 252 on the second hole transport layer 242, the light-emitting layer containing a light-emitting layer host material and a light-emitting layer guest material;

[0080] (10) vacuum evaporating an electron transport material as a second electron transport layer 262 on the second light-emitting layer 252;

[0081] (11) vacuum evaporating an electron injection material as an electron injection layer 28 on the second electron transport layer 262;

[0082] (12) vacuum evaporating a cathode material as a cathode electrode 29 on the electron injection layer 28.

[0083] The above describes only one typical structure of an organic electroluminescent device and a method of fabricating the same, and it should be understood that the present application is not limited to this structure. The charge generation layer material of the present application can be used in an organic electroluminescent device of any structure, and the organic electroluminescent device can be fabricated using any method known in the art.

[0084] The present application also provides a display device including the organic electroluminescent device of the present application described above. The display device includes, but is not limited to, a display, a television, a tablet, a mobile communication terminal, etc.

[0085] The method of synthesizing the compound of the present application is not particularly limited, and any method known to those skilled in the art can be used for the synthesis. The following illustrates the synthesis of the compound of the present application.

[0086] Synthesis Example 1: Synthesis of Compound A1

[0087]

[0088] In a reaction flask, 100 mmol of p-chlorobromobenzene, 100 mmol of diphenylphosphine oxide, 41.4 g of potassium carbonate (300 mmol), 800 mL of toluene, and 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) were added, and the reaction was performed at 80°C for 12 h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M1. Herein, the amount of Pd(PPh3)4 added was 1 mol% of p-chlorobromobenzene.

[0089] In a reaction flask, 100 mmol of M1, 100 mmol of pinacol diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane, and 1 mol% of Pd(PPh3)4 were added, and the reaction was performed at 100°C for 12 h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M2. Herein, the amount of Pd(PPh3)4 added was 1 mol% of M1.

[0090] In a reaction flask, 100 mmol of 2-bromonaphthalene, 100 mmol of p-chlorophenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of tetrahydrofuran (THF), 200 mL of water, and 1 mol% of Pd(PPh3)4 were added, and the reaction was performed at 60°C for 12 h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M3. Herein, the amount of Pd(PPh3)4 added was 1 mol% of 2-bromonaphthalene.

[0091] In a reaction bottle, 100 mmol of M3, 100 mmol of bis(pinacolato)diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane, and 1 mol% of Pd(PPh3)4 were added, and reacted at 100°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M4. Herein, the amount of Pd(PPh3)4 added was 1 mol% of M3.

[0092] In a reaction bottle, 100 mmol of 2,9-dichloro-1,10-phenanthroline, 100 mmol of M4, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and reacted at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M5. Herein, the amount of Pd(PPh3)4 added was 1 mol% of 2,9-dichloro-1,10-phenanthroline.

[0093] In a reaction bottle, 100 mmol of M2, 100 mmol of M5, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and reacted at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder A1. Herein, the amount of Pd(PPh3)4 added was 1 mol% of M2.

[0094] 1 H NMR (400 MHz, Chloroform) δ 8.70 (d, J = 8.0 Hz, 2H), 8.38 (d, J = 7.2 Hz, 2H), 8.34 (d, J = 7.6 Hz, 2H), 8.05 (t, J = 7.6 Hz, 2H), 7.98 (t, J = 7.2 Hz, 3H), 7.90-7.84 (m, 3H), 7.80-7.75 (m, 4H), 7.65-7.47 (m, 10H), 7.36 (d, J = 7.2 Hz, 1H), 7.30 (d, J = 8.0 Hz, 2H).

[0095] Synthesis Example 2: Synthesis of Compound A4

[0096]

[0097] In a reaction flask, 100 mmol of p-chlorobromobenzene, 100 mmol of diphenylphosphine oxide, 41.4 g of potassium carbonate (300 mmol), 800 mL of toluene, and 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) were added, and the reaction was performed at 80°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction material was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M1. Herein, the addition amount of Pd(PPh3)4 was 1 mol% of p-chlorobromobenzene.

[0098] In a reaction flask, 100 mmol of M1, 100 mmol of pinacol diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane, and 1 mol% of Pd(PPh3)4 were added, and the reaction was performed at 100°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction material was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M2. Herein, the addition amount of Pd(PPh3)4 was 1 mol% of M1.

[0099] In a reaction flask, 100 mmol of 3-bromoquinoline, 100 mmol of p-chlorobenzeneboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of tetrahydrofuran (THF), and 200 mL of water, and 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) were added, and the reaction was performed at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction material was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M3. Herein, the addition amount of Pd(PPh3)4 was 1 mol% of 3-bromoquinoline.

[0100] In a reaction flask, 100 mmol of M3, 100 mmol of pinacol diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane, and 1 mol% of Pd(PPh3)4 were added, and the reaction was performed at 100°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction material was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M4. Herein, the addition amount of Pd(PPh3)4 was 1 mol% of M3.

[0101] In a reaction bottle, 100 mmol of 2,9-dichloro-1,10-phenanthroline, 100 mmol of M4, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and reacted at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M5. Herein, the amount of Pd(PPh3)4 added was 1 mol% of 2,9-dichloro-1,10-phenanthroline.

[0102] In a reaction bottle, 100 mmol of M2, 100 mmol of M5, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and reacted at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder A4. Herein, the amount of Pd(PPh3)4 added was 1 mol% of M2.

[0103] 1 H NMR (400 MHz, Chloroform) δ 8.68 (d, J = 7.2 Hz, 2H), 8.45 (s, 1H), 8.42 (d, J = 7.2 Hz, 1H), 8.32 (d, J = 7.6 Hz, 3H), 8.26 (s, 1H), 8.22 (d, J = 7.2 Hz, 1H), 7.98 (d, J = 8.0 Hz, 2H), 7.86 (d, J = 7.2 Hz, 1H), 7.81 - 7.68 (m, 6H), 7.56 (d, J = 7.2 Hz, 2H), 7.52 - 7.45 (m, 6H), 7.34 (d, J = 8.0 Hz, 2H), 7.25 (d, J = 7.6 Hz, 2H).

[0104] Synthesis Example 3: Synthesis of Compound A10

[0105]

[0106] In a reaction flask, 100 mmol of p-chlorobromobenzene, 100 mmol of diphenylphosphine oxide, 41.4 g of potassium carbonate (300 mmol), 800 mL of toluene, and 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) were added, and the reaction was performed at 80°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M1. Herein, the amount of Pd(PPh3)4 added was 1 mol% of p-chlorobromobenzene.

[0107] In a reaction flask, 100 mmol of M1, 100 mmol of pinacol diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane, and 1 mol% of Pd(PPh3)4 were added, and the reaction was performed at 100°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M2. Herein, the amount of Pd(PPh3)4 added was 1 mol% of M1.

[0108] In a reaction flask, 100 mmol of 3-bromofluoranthene, 100 mmol of p-chlorobenzeneboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF and 200 mL of water, and 1 mol% of Pd(PPh3)4 were added, and the reaction was performed at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M3. Herein, the amount of Pd(PPh3)4 added was 1 mol% of 3-bromofluoranthene.

[0109] In a reaction flask, 100 mmol of M3, 100 mmol of pinacol diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane, and 1 mol% of Pd(PPh3)4 were added, and the reaction was performed at 100°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M4. Herein, the amount of Pd(PPh3)4 added was 1 mol% of M3.

[0110] In a reaction flask, 100 mmol of 2,9-dichloro-1,10-phenanthroline, 100 mmol of M4, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and reacted at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M5. Herein, the amount of Pd(PPh3)4 added was 1 mol% of 2,9-dichloro-1,10-phenanthroline.

[0111] In a reaction flask, 100 mmol of M2, 100 mmol of M5, 41.4 g of potassium carbonate (300 mmol), 800 mL of tetrahydrofuran (THF), and 200 mL of water were added, and 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) was added, and reacted at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder A10. Herein, the amount of Pd(PPh3)4 added was 1 mol% of M2.

[0112] 1 H NMR (400 MHz, Chloroform) δ 8.72 (d, J = 7.2 Hz, 2H), 8.45-8.34 (m, 6H), 8.10 (d, J = 6.8 Hz, 2H), 7.96 (d, J = 7.6 Hz, 2H), 7.88 (d, J = 7.2 Hz, 1H), 7.82-7.75 (m, 5H), 7.66 (d, J = 7.2 Hz, 2H), 7.60-7.45 (m, 8H), 7.36 (t, J = 7.6 Hz, 3H), 7.24 (d, J = 7.2 Hz, 2H).

[0113] Synthesis Example 4: Synthesis of Compound A14

[0114]

[0115] In a reaction flask, 100 mmol of 2-bromo-5-chloropyridine, 100 mmol of 1-naphthaleneboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of toluene, and 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) were added, and reacted at 80°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M1. Herein, the amount of Pd(PPh3)4 added was 1 mol% of 2-bromo-5-chloropyridine.

[0116] In a reaction flask, 100 mmol of Ml, 100 mmol of bis(pinacolato)diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane, and 1 mol% of Pd(PPh3)4 were added, and reacted at 100°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M2. The amount of Pd(PPh3)4 added was 1 mol% of Ml.

[0117] In a reaction flask, 100 mmol of p-chlorobromobenzene, 100 mmol of M2, 41.4 g of potassium carbonate (300 mmol), 800 mL of tetrahydrofuran (THF), and 200 mL of water were added, and 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) was added, and reacted at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M3. The amount of Pd(PPh3)4 added was 1 mol% of p-chlorobromobenzene.

[0118] In a reaction flask, 100 mmol of M3, 100 mmol of bis(pinacolato)diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane, and 1 mol% of Pd(PPh3)4 were added, and reacted at 100°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M4. The amount of Pd(PPh3)4 added was 1 mol% of M3.

[0119] In a reaction flask, 100 mmol of p-chlorobromobenzene, 100 mmol of diethylphosphine oxide, 41.4 g of potassium carbonate (300 mmol), 800 mL of toluene, and 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) were added, and reacted at 80°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M5. The amount of Pd(PPh3)4 added was 1 mol% of p-chlorobromobenzene.

[0120] In a reaction bottle, 100 mmol of M5, 100 mmol of bis(pinacolato)diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane, and 1 mol% of Pd(PPh3)4 were added, and reacted at 100°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, water-washed, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M6. Herein, the amount of Pd(PPh3)4 added was 1 mol% of M5.

[0121] In a reaction bottle, 100 mmol of 2,9-dichloro-1,10-phenanthroline, 100 mmol of M6, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and reacted at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, water-washed, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M7. Herein, the amount of Pd(PPh3)4 added was 1 mol% of 2,9-dichloro-1,10-phenanthroline.

[0122] In a reaction bottle, 100 mmol of M4, 100 mmol of M7, 41.4 g of potassium carbonate (300 mmol), 800 mL of tetrahydrofuran (THF), and 200 mL of water were added, and 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) was added, and reacted at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, water-washed, and the obtained solid was purified by recrystallization with toluene to obtain a white powder A14. Herein, the amount of Pd(PPh3)4 added was 1 mol% of M4.

[0123] 1 H NMR (400 MHz, Chloroform) δ 8.94 (d, J = 7.2 Hz, 1H), 8.88 (s, 1H), 8.72 (d, J = 7.2 Hz, 2H), 8.40 (d, J = 7.2 Hz, 2H), 8.20 (d, J = 7.2 Hz, 1H), 8.16 (d, J = 7.6 Hz, 2H), 8.04 - 7.82 (m, 6H), 7.58 (d, J = 6.8 Hz, 1H), 7.49 - 7.42 (m, 4H), 7.36 (d, J = 7.6 Hz, 2H), 7.24 (d, J = 7.2 Hz, 2H), 2.68 - 2.54 (m, 4H), 1.30 (t, 6H).

[0124] Synthesis Example 5: Synthesis of Compound A26

[0125]

[0126] In a reaction bottle, 100 mmol of 2-bromo-5-chloropyridine, 100 mmol of 2-naphthaleneboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of toluene, and 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) were added, and reacted at 80°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M1. Herein, the addition amount of Pd(PPh3)4 was 1 mol% of 2-bromo-5-chloropyridine.

[0127] In a reaction bottle, 100 mmol of M1, 100 mmol of pinacol diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane, and 1 mol% of Pd(PPh3)4 were added, and reacted at 100°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M2. Herein, the addition amount of Pd(PPh3)4 was 1 mol% of M1.

[0128] In a reaction bottle, 100 mmol of p-chlorobromobenzene, 100 mmol of M2, 41.4 g of potassium carbonate (300 mmol), 800 mL of tetrahydrofuran (THF) and 200 mL of water, and 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) were added, and reacted at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M3. Herein, the addition amount of Pd(PPh3)4 was 1 mol% of p-chlorobromobenzene.

[0129] In a reaction bottle, 100 mmol of M3, 100 mmol of pinacol diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane, and 1 mol% of Pd(PPh3)4 were added, and reacted at 100°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M4. Herein, the addition amount of Pd(PPh3)4 was 1 mol% of M3.

[0130] In a reaction bottle, 100 mmol of 4-bromophenyl- triphenyl germanium, 100 mmol of pinacol diboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane, and 1 mol% of Pd(PPh3)4 were added, and reacted at 100°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, water-washed, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M6. Herein, the amount of Pd(PPh3)4 added was 1 mol% of M5.

[0131] In a reaction bottle, 100 mmol of 2,9-dichloro-1,10-phenanthroline, 100 mmol of M5, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF and 200 mL of water, and 1 mol% of Pd(PPh3)4 were added, and reacted at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, water-washed, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M6. Herein, the amount of Pd(PPh3)4 added was 1 mol% of 2,9-dichloro-1,10-phenanthroline.

[0132] In a reaction bottle, 100 mmol of M4, 100 mmol of M6, 41.4 g of potassium carbonate (300 mmol), 800 mL of tetrahydrofuran (THF) and 200 mL of water, and 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) were added, and reacted at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, water-washed, and the obtained solid was purified by recrystallization with toluene to obtain a white powder A26. Herein, the amount of Pd(PPh3)4 added was 1 mol% of M4.

[0133] 1 H NMR (400 MHz, Chloroform) δ 8.85 (s, 1H), 8.76 (s, 1H), 8.70 (d, J = 7.6 Hz, 2H), 8.40 (d, J = 10.0 Hz, 2H), 8.32 (d, J = 7.6 Hz, 1H), 8.10 - 7.96 (m, 6H), 7.88 (d, J = 7.2 Hz, 1H), 7.65 - 7.56 (m, 4H), 7.44 (d, J = 8.0 Hz, 2H), 7.36 (d, J = 8.0 Hz, 2H), 7.30 - 7.15 (m, 11H), 7.12 - 7.05 (m, 6H).

[0134] Synthesis Example 6: Synthesis of Compound A38

[0135]

[0136] In a reaction bottle, 100 mmol of p-chlorobromobenzene, 100 mmol of diphenylarsine oxide, 41.4 g of potassium carbonate (300 mmol), 800 mL of toluene, and 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) were added, and reacted at 80°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M1. Herein, the addition amount of Pd(PPh3)4 was 1 mol% of p-chlorobromobenzene.

[0137] In a reaction bottle, 100 mmol of M1, 100 mmol of pinacol diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane, and 1 mol% of Pd(PPh3)4 were added, and reacted at 100°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M2. Herein, the addition amount of Pd(PPh3)4 was 1 mol% of M1.

[0138] In a reaction bottle, 100 mmol of 3-bromodibenzothiophene, 100 mmol of p-chlorophenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF and 200 mL of water, and 1 mol% of Pd(PPh3)4 were added, and reacted at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M3. Herein, the addition amount of Pd(PPh3)4 was 1 mol% of 3-bromodibenzothiophene.

[0139] In a reaction bottle, 100 mmol of M3, 100 mmol of pinacol diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane, and 1 mol% of Pd(PPh3)4 were added, and reacted at 100°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M4. Herein, the addition amount of Pd(PPh3)4 was 1 mol% of M3.

[0140] In a reaction bottle, 100 mmol of 2,9-dichloro-1,10-phenanthroline, 100 mmol of M4, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and reacted at 60°C for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M5. The amount of Pd(PPh3)4 added was 1 mol% of 2,9-dichloro-1,10-phenanthroline.

[0141] In a reaction bottle, 100 mmol of M2, 100 mmol of M5, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and reacted at 60°C for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder A38. The amount of Pd(PPh3)4 added was 1 mol% of M2.

[0142] 1 H NMR (400 MHz, Chloroform) δ 8.72 (d, J = 7.2 Hz, 2H), 8.46 (d, J = 7.2 Hz, 1H), 8.42 - 8.34 (m, 5H), 8.17 (d, J = 7.2 Hz, 1H), 7.98 (d, J = 7.6 Hz, 3H), 7.90 - 7.82 (m, 4H), 7.80 - 7.74 (m, 4H), 7.58 (d, J = 7.2 Hz, 2H), 7.54 - 7.42 (m, 6H), 7.32 (d, J = 8.0 Hz, 2H), 7.28 (t, J = 7.2 Hz, 1H).

[0143] Other compounds of the present application can be synthesized according to the above synthesis example, selecting appropriate starting materials, or any other suitable method and starting materials.

[0144] Example 1

[0145] A glass substrate coated with a 150 nm-thick ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone-ethanol mixed solvent, baked in a clean environment until the water was completely removed, cleaned with ultraviolet light and ozone, and the surface was bombarded with a low-energy cation beam to obtain a glass substrate with an anode.

[0146] Then, the glass substrate with an anode was placed in a vacuum chamber, vacuumed to less than 10-5 vacuum evaporating a first hole injection layer on the anode layer film of the glass substrate with anode, the material of the first hole injection layer comprising hole injection layer material HT-11 and p-type dopant p-1, and the evaporation being performed by the method of multi-source co-evaporation, wherein the evaporation rate of the hole injection layer material HT-11 is adjusted to be 0.1 nm / s, the evaporation rate of the p-type dopant p-1 is 3% of the evaporation rate of the hole injection layer material HT-11, and the total film thickness of the evaporation is 10 nm; the hole injection layer material HT-11 and the p-type dopant p-1 are as follows:

[0147]

[0148] Then, vacuum evaporating hole transport layer material HT-5 as a first hole transport layer on the first hole injection layer, wherein the evaporation rate is 0.1 nm / s, the evaporation film thickness is 80 nm, and the hole transport layer material HT-5 is as follows:

[0149]

[0150] Then, vacuum evaporating a first light emitting layer on the first hole transport layer, the first light emitting layer comprising light emitting layer host material BH-5 and light emitting layer guest material BD-3, and the evaporation being performed by the method of multi-source co-evaporation, wherein the evaporation rate of the light emitting layer host material BH-5 is adjusted to be 0.1 nm / s, the evaporation rate of the light emitting layer guest material BD-1 is 3% of the evaporation rate of the light emitting layer host material BH-5, and the evaporation film thickness is 30 nm; the light emitting layer host material BH-5 and the light emitting layer guest material BD-3 are as follows:

[0151]

[0152] Then, vacuum evaporating a first electron transport layer on the first light emitting layer, the material of the first electron transport layer being compound ET30 and LiQ, wherein the evaporation rate of the compound ET30 is 0.1 nm / s, the evaporation rate ratio of the compound ET30 and LiQ is 7:3, and the total film thickness of the evaporation is 30 nm; the compound ET30 and LiQ are as follows:

[0153]

[0154] The above first hole injection layer, first hole transport layer, first light emitting layer and first electron transport layer together form a first light emitting unit;

[0155] On the first electron transport layer which is the uppermost layer in the first light emitting unit, evaporating compound A1 provided by the present application and metal ytterbium (Yb) as a charge generation layer, wherein the evaporation rate of the compound A1 is 0.01 nm / s, the evaporation rate ratio of the compound A1 and Yb is 99:1, and the total film thickness of the evaporation is 10 nm;

[0156] A second hole injection layer is evaporated on the charge generation layer, the material of the second hole injection layer comprises a hole injection layer material HT-11 and a p-type dopant p-1, wherein the evaporation rate of the hole injection layer material HT-11 is adjusted to be 0.1 nm / s, the evaporation rate ratio of the hole injection layer material HT-11 and the p-type dopant p-1 is 99:1, and the total film thickness of the evaporation is 10 nm;

[0157] Then, a hole transport layer material HT-5 is vacuum evaporated on the second hole injection layer as a second hole transport layer, wherein the evaporation rate is 0.1 nm / s, and the film thickness of the evaporation is 80 nm;

[0158] Then, a second light-emitting layer is vacuum evaporated on the second hole transport layer, the second light-emitting layer comprises a light-emitting layer host material BH-5 and a light-emitting layer guest material BD-3, and the evaporation is performed by a multi-source co-evaporation method, wherein the evaporation rate of the light-emitting layer host material BH-5 is adjusted to be 0.1 nm / s, the evaporation rate of the light-emitting layer guest material BD-3 is 3% of the evaporation rate of the light-emitting layer host material BH-5, and the total film thickness of the evaporation is 30 nm;

[0159] Then, a second electron transport layer is vacuum evaporated on the second light-emitting layer, the electron transport material is a compound ET30 and LiQ, wherein the evaporation rate of the compound ET30 is 0.1 nm / s, the evaporation rate ratio of the compound ET30 and the LiQ is 7:3, and the total film thickness of the evaporation is 30 nm;

[0160] The above second hole injection layer, second hole transport layer, second light-emitting layer and second electron transport layer together form a second light-emitting unit;

[0161] Then, a LiF with a thickness of 0.5 nm is vacuum evaporated on the uppermost second electron transport layer in the second light-emitting unit as an electron injection layer, wherein the evaporation rate is 0.1 nm / s;

[0162] Finally, an Al layer with a thickness of 150 nm is vacuum evaporated on the electron injection layer as a cathode electrode of the organic electroluminescent device, wherein the evaporation rate is 0.1 nm / s.

[0163] Example 2-6

[0164] Except that the charge generation layer material is replaced by A4, A10, A14, A26 and A38 respectively instead of A1, the rest is the same as Example 1.

[0165] Comparative Example 1

[0166] Except that the charge generation layer material is replaced by CGL00R1 instead of A1, the rest is the same as Example 1, and the structure of CGL00R1 is as follows:

[0167]

[0168] Comparative Example 2

[0169] Except that the charge generation layer material is selected to be CGL00R6 instead of Al, the rest is the same as Example 1, and the structure of CGL00R6 is shown as follows:

[0170]

[0171] Comparative Example 3

[0172] Except that the charge generation layer material is selected to be R1 instead of Al, the rest is the same as Example 1, and the structure of R1 is shown as follows:

[0173]

[0174] Comparative Example 4

[0175] Except that the charge generation layer material is selected to be R2 instead of Al, the rest is the same as Example 1, and the structure of R2 is shown as follows:

[0176]

[0177] The organic electroluminescent devices prepared by the above process were subjected to the following performance tests:

[0178] The driving voltage, current efficiency and device lifetime of the organic electroluminescent devices prepared in Example 1 to Example 6 and Comparative Example 1 to Comparative Example 4 were measured at the same brightness using a digital source meter and a luminance meter. Specifically, the voltage was increased at a rate of 0.1 V per second, and the voltage at which the brightness of the organic electroluminescent device reached 1000 cd / m 2 was measured, i.e. the driving voltage, and the current density at this time was also measured; the ratio of brightness to current density was the current efficiency; the LT95 lifetime test was as follows: at a brightness of 1000 cd / m 2 , a constant current was maintained, and the time for the brightness of the organic electroluminescent device to drop to 950 cd / m 2 was measured in hours. The results are shown in Table 1.

[0179] Table 1. Performance results of organic electroluminescent devices

[0180]

[0181] As can be seen from Table 1, the organic electroluminescent devices prepared in Examples 1 to 6 adopt the compounds A1, A4, A9, A14, A26 and A38 provided by the present application as the charge generation layer material, and compared with the organic electroluminescent devices prepared in Comparative Examples 1 to 4 which adopt the known materials in the prior art as the charge generation layer material, the organic electroluminescent devices of Examples 1 to 6 have lower driving voltage, higher current efficiency and longer LT95 lifetime. Therefore, it is proved that when the compound of formula (I) is used as the charge generation layer material in the organic electroluminescent device, the driving voltage can be effectively reduced, the current efficiency can be improved, and the service life of the device can be prolonged. The material of the present application has significantly improved performance in improving the efficiency and prolonging the service life of the organic electroluminescent device, and can obtain an organic electroluminescent device with good performance.

[0182] The above description is merely preferred embodiments of the present application, but not to limit the present application. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present application shall be included in the protection scope of the present application.

Claims

1. A compound, characterized in that, having the structure of Formula (I): L 1 、L 2 、L 3 each independently is selected from a chemical bond, C6-C20 30 arylene, which is unsubstituted or substituted by Rc, C3-C20 30 heteroarylene; A is selected from C 10 -C 30 aryl, C9-Ci4 30 heteroaryl; B is selected from the following structures: R1-R7 are each independently selected from C1-C4 alkanes, unsubstituted or Rc-substituted C6-C alkanes. 18 Aromatic group, unsubstituted or Rc-substituted C3-C 18 Mixed aromatics; the heteroatoms on the heteroaryl or heteroarylene group are each independently selected from O, S, or N; Rc is each independently selected from hydrogen, deuterium, halogen, nitro, cyano, C1-C4 alkyl, phenyl, biphenyl, terphenyl, pyridyl, pyrimidyl, or naphthyl.

2. The compound of claim 1, wherein R1-R7 are each independently selected from methyl, ethyl, isopropyl, tert-butyl, a group of the following compounds unsubstituted or substituted with Rc: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, dibenzofuran, dibenzothiophene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, spirofluorene.

3. The compound of claim 1, wherein L 1 , L 2 , L 3 are each independently selected from the group consisting of a bond, a radical of phenyl, pyridyl, pyrimidyl, quinoxalyl, quinazolyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, anthryl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, unsubstituted or substituted with Rc.

4. The compound of claim 1, wherein A is selected from the following structures:

5. The compound of claim 1, wherein selected from the compounds of A1 to A40:

6. A charge generation layer material characterized by, comprising at least one of the compounds of any one of claims 1-5.

7. The charge generation layer material according to claim 6, wherein Li or Yb is further included in a mass percentage of 0.5%-2.5% of the charge generation layer material.

8. An organic electroluminescent device, characterized by comprising a charge generation layer and an electron transport layer, the charge generation layer comprising at least one of the charge generation layer materials of claim 6 or 7.

9. The organic electroluminescent device according to claim 8, characterized in that the thickness of the charge generation layer is 10 nm-30 nm, and the thickness of the electron transport layer is 10 nm-40 nm.

10. A display device, characterized by comprising: comprising the organic electroluminescence device of claim 8 or 9.

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