Bisbipyridine substituted compound and use thereof

Abstract

The application provides a compound having a structure shown in formula (I). The compound has a parent structure of an ortho-disubstituted pyridine fragment, has a large conjugate plane, high bond energy between atoms, and has a suitable energy level between adjacent layers when used as an electron transport material and / or a charge generation material, is beneficial to electron injection and migration, can effectively reduce a driving voltage, and has a high electron migration rate, thereby improving the light-emitting efficiency of an organic electroluminescent device. The compound is used as an electron transport material and / or a charge generation material in the organic electroluminescent device, so that the driving voltage of the organic electroluminescent device is reduced, the light-emitting efficiency of the organic electroluminescent device is improved, and the service life of the organic electroluminescent device is prolonged.

Description

Technical Field

[0001] This application relates to the field of organic light-emitting display technology, and in particular to a compound and its uses, an electron transport material, a charge generating material, an organic electroluminescent device, and a display device. Background Technology

[0002] Electroluminescence (EL) refers to the phenomenon where a luminescent material emits light when excited by an electric field and subjected to current and voltage. It is a process that directly converts electrical energy into light energy. Organic electroluminescent displays (OLEDs) possess a series of advantages, including self-illumination, low-voltage DC drive, all-solid-state operation, wide viewing angle, light weight, and simple composition and manufacturing process. Compared to liquid crystal displays (LCDs), OLEDs do not require a backlight, have a wider viewing angle, lower power consumption, and a response speed up to 1000 times faster than LCDs, while their manufacturing cost is lower than that of LCDs with equivalent resolution. Therefore, organic electroluminescent devices have a very broad application prospect.

[0003] With the continuous advancement of OLED technology in the fields of lighting and display, people are paying more attention to the research of high-efficiency organic materials that affect the performance of OLED devices. An efficient and long-life organic electroluminescent device is usually the result of the optimized combination of device structure and various organic materials, which provides chemists with great opportunities and challenges to design and develop functional materials with various structures.

[0004] Compared to inorganic light-emitting materials, organic electroluminescent materials have many advantages, such as: good processability (they can be deposited on any substrate through vapor deposition or spin coating), the ability to achieve flexible and large-area displays, and the ability to adjust the optical, electrical, and stability properties of the materials by modifying their molecular structure, offering a wide range of material choices. The most common OLED device structures typically include the following types of organic materials: hole injection materials, hole transport materials, electron transport materials, and light-emitting materials (including host and guest materials). Among these, electron transport materials and charge-generating materials are crucial functional materials. Electron transport materials directly affect electron mobility, while charge-generating materials significantly influence the charge generation rate, ultimately affecting the OLED's luminous efficiency. To improve the luminous efficiency of OLEDs, new electron transport and charge-generating materials are still needed in this field. Summary of the Invention

[0005] The purpose of this application is to provide a compound that, when used as an electron transport material and / or charge generating material, can improve the luminous efficiency and lifespan of organic electroluminescent devices. The specific technical solution is as follows:

[0006] The first aspect of this application provides a compound having the structural formula shown in (I):

[0007]

[0008] in,

[0009] L 1 and L 2 Each is independently selected from chemical bonds, unsubstituted or Rc-substituted C6-C. 30 aryl, unsubstituted or Rc-substituted C3-C 30 heteroaryl;

[0010] X 1 -X 5 Each is independently selected from CR or N, and X 1 -X 5 At least one of them is selected from N, and R is selected from hydrogen, deuterium, C1-C4 alkyl, C2-C6 alkenyl, unsubstituted or Rc-substituted C6-C 30 Aryl, unsubstituted or Rc-substituted C3-C 30 Heteroaryl groups, and adjacent R groups can form a ring; when X 1 -X 5 When there are multiple selections from CR, the R in each CR can be the same or different;

[0011] Q is selected from Any one of the following, and the hydrogen atoms in Q can be independently substituted by Ra, where Ra is selected from C1-C4 alkyl, unsubstituted or Rc-substituted C6-C 30 Aryl, unsubstituted or Rc-substituted C3-C 30 heteroaryl, L 2 Connect to any connectable position in Q;

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

[0013] The substituents Rc of each group are independently selected from deuterium, halogen, nitro, cyano, C1-C4 alkyl, phenyl, biphenyl, terphenyl, and naphthyl.

[0014] A second aspect of this application provides the use of the above-mentioned compound as a functional layer material for organic electroluminescent devices.

[0015] A third aspect of this application provides an electron transport material comprising at least one of the compounds described above.

[0016] A fourth aspect of this application provides a charge-generating material comprising at least one of the compounds described above.

[0017] The fifth aspect of this application provides an organic electroluminescent device comprising at least one of the electron transport material and / or charge generating material described above.

[0018] A sixth aspect of this application provides a display device comprising the aforementioned organic electroluminescent device.

[0019] Beneficial effects of the embodiments in this application:

[0020] The compounds provided in this application have a parent structure of ortho-disubstituted pyridine fragments, possessing a large conjugated plane and high interatomic bond energy, which is conducive to solid-state stacking of molecules, thus exhibiting good thermal stability. When applied to organic light-emitting diodes (OLEDs), these compounds help extend the lifespan of the OLEDs. When used as electron transport materials, they possess good electron transport efficiency and appropriate energy level with adjacent layers, facilitating electron injection and migration, thereby effectively reducing the driving voltage of the OLED. They also have a high electron migration rate, thus improving the luminous efficiency of the OLED. When used as charge-generating materials, they can improve charge-generating efficiency, especially for charge-generating layers containing metals such as Li or Yb. The compounds in this application can form good complexes with these metals, improving charge-generating efficiency, thereby effectively enhancing the luminous efficiency of the OLED and reducing its driving voltage. The OLEDs of this application, containing the compounds as electron transport materials and / or charge-generating materials, can effectively reduce the driving voltage of the OLED, improve its luminous efficiency, and extend its lifespan. The display device provided in this application has excellent display effects.

[0021] Of course, implementing any product or method of this application does not necessarily require achieving all of the advantages described above at the same time. Attached Figure Description

[0022] To more clearly illustrate the technical solutions in the embodiments of this application or the prior art, the drawings used in the description of the embodiments or the prior art will be briefly introduced below. Obviously, the drawings described below are only some embodiments of this application. For those skilled in the art, other embodiments can be obtained based on these drawings.

[0023] Figure 1 This is a schematic diagram of a typical organic electroluminescent device.

[0024] Figure 2 This is a schematic diagram of another typical organic electroluminescent device. Detailed Implementation

[0025] The technical solutions of the embodiments of this application will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some embodiments of this application, and not all embodiments. Based on the embodiments of this application, all other embodiments obtained by those skilled in the art based on this application are within the scope of protection of this application.

[0026] The first aspect of this application provides a compound having the structural formula shown in (I):

[0027]

[0028] in,

[0029] L 1 and L 2 Each is independently selected from chemical bonds, unsubstituted or Rc-substituted C6-C. 30 aryl, unsubstituted or Rc-substituted C3-C 30 heteroaryl;

[0030] X 1 -X 5 Each is independently selected from CR or N, and X 1 -X 5 At least one of them is selected from N, and R is selected from hydrogen, deuterium, C1-C4 alkyl, C2-C6 alkenyl, unsubstituted or Rc-substituted C6-C 30 Aryl, unsubstituted or Rc-substituted C3-C 30 Heteroaryl groups, and adjacent R groups can form a ring; when X 1 -X 5 When there are multiple selections from CR, the R in each CR can be the same or different;

[0031] Q is selected from Any one of the following, and the hydrogen atoms in Q can be independently substituted by Ra, where Ra is selected from C1-C4 alkyl, unsubstituted or Rc-substituted C6-C 30 Aryl, unsubstituted or Rc-substituted C3-C 30 heteroaryl, L 2 Connect to any connectable position in Q; the above "hydrogen atoms in Q can be independently replaced by Ra" means that hydrogen atoms in Q are not replaced, or one or more hydrogen atoms in Q can be independently replaced by Ra.

[0032] The heteroatoms in the heteroaryl or heteroaryl groups are each independently selected from O, S, and N;

[0033] The substituents Rc of each group are independently selected from deuterium, halogen, nitro, cyano, C1-C4 alkyl, phenyl, biphenyl, terphenyl, and naphthyl.

[0034] Preferably, L 1 and L 2 Each is independently selected from chemical bonds, unsubstituted or Rc-substituted C6-C. 18 aryl, unsubstituted or Rc-substituted C3-C 12 Heteroaryl; Ra is selected from C1-C4 alkyl, unsubstituted or Rc-substituted C6-C 18 Aryl, unsubstituted or Rc-substituted C3-C 12 Heteroaryl; R is selected from hydrogen, deuterium, C1-C4 alkyl, C2-C4 alkenyl, unsubstituted or Rc-substituted C6-C 18 Aryl, unsubstituted or Rc-substituted C3-C 18 Mixed aromatic compounds.

[0035] More preferably, Ra is selected from methyl, ethyl, unsubstituted or Rc-substituted groups of the following: phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, fluorenyl, pyridinyl, pyridinyl, pyrazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, cyclolinyl, naphthinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, benzothiopheneyl, dibenzothiopheneyl, aza-dibenzothiopheneyl, 9,9-dimethylfluorenyl, spirodifluorenyl.

[0036] More preferably, L 1 and L 2 Each of the following subunits, independently selected from chemical bonds, unsubstituted or Rc-substituted, is selected from: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, quinazoline, quinoxaline, cyclophosphine, triazine, pyridopyrazine, furan, benzofuran, dibenzofuran, aza-dibenzofuran, benzothiophene, dibenzothiophene, aza-dibenzothiophene, 9,9-dimethylfluorene, spirodifluorene, and phenylpyridine.

[0037] More preferably, R is independently selected from hydrogen, deuterium, methyl, ethyl, vinyl, unsubstituted or Rc-substituted groups of the following: phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, fluorenyl, pyridinyl, pyridinyl, pyrazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, cyclolinyl, naphthinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, benzothiophene, dibenzothiophene, aza-dibenzothiophene, 9,9-dimethylfluorenyl, spirodifluorenyl.

[0038] For example, the above compounds are selected from the compounds shown in A1 to A25 below:

[0039]

[0040]

[0041] The second aspect of this application provides the use of the above-mentioned compound as a functional layer material in an organic electroluminescent device (OLED). Preferably, the functional layer is at least one of an electron transport layer and a charge generation layer. When applied in the electron transport layer, the compound provided in this application exhibits good electron transport efficiency and a suitable energy level with adjacent layers, which is beneficial for electron injection and migration, thereby effectively reducing the driving voltage of the OLED. It also has a high electron migration rate, thereby improving the luminous efficiency of the OLED. When applied in the charge generation layer, the compound provided in this application can improve the charge generation efficiency. Especially for charge generation layers containing metals Li or Yb, the compound can form good complexation with these metals to improve charge generation efficiency, thereby effectively enhancing the luminous efficiency of the OLED and reducing its driving voltage.

[0042] A third aspect of this application provides an electron transport material comprising at least one of the aforementioned compounds. When applied in an electron transport layer, the electron transport material provided by this application exhibits a suitable energy level with adjacent layers, which facilitates electron injection and migration, thereby effectively reducing the driving voltage of the organic light-emitting device (OLED). Simultaneously, it possesses a high electron migration rate, thereby improving the luminous efficiency of the OLED. Furthermore, the electron transport material of this application exhibits good thermal stability, which is beneficial for extending the lifespan of the OLED.

[0043] A fourth aspect of this application provides a charge-generating material comprising at least one of the aforementioned compounds. When applied in a charge-generating layer, the charge-generating material provided by this application exhibits suitable energy level levels with adjacent layers, which is beneficial for charge generation, thereby effectively reducing the driving voltage of the organic light-emitting device and improving its luminous efficiency. Furthermore, the charge-generating material of this application possesses good thermal stability, which is beneficial for extending the lifespan of the organic light-emitting device.

[0044] A fifth aspect of this application provides an organic electroluminescent device comprising at least one of the aforementioned electron transport material and / or charge generation layer. Therefore, the organic electroluminescent device provided by this application has a lower driving voltage, higher luminous efficacy, and longer lifespan.

[0045] In this application, there are no particular limitations on the type and structure of organic electroluminescent devices. They can be various types and structures of organic electroluminescent devices known in the art, as long as at least one of the electron transport material and / or charge generation layer provided in this application can be used.

[0046] In some embodiments of this application, the organic electroluminescent device can be a top-emitting structure, which may include, on a substrate, an anode, a hole injection layer, a hole transport layer, an emissive layer, an electron transport layer, an electron injection layer, and a transparent or semi-transparent cathode in sequence. The organic electroluminescent device can also be a bottom-emitting structure, which may include, on a substrate, a transparent or semi-transparent anode, a hole injection layer, a hole transport layer, an emissive layer, an electron transport layer, an electron injection layer, and a cathode in sequence. The organic electroluminescent device can also be a dual-sided emissive structure, which may include, on a substrate, a transparent or semi-transparent anode, a hole injection layer, a hole transport layer, an emissive layer, an electron transport layer, an electron injection layer, and a transparent or semi-transparent cathode in sequence.

[0047] Additionally, an electron blocking layer may be present between the hole transport layer and the light-emitting layer, and a hole blocking layer may be present between the light-emitting layer and the electron transport layer. A light extraction layer may be disposed on the transparent electrode on the light-emitting side. However, the structure of the organic electroluminescent device of this application is not limited to the specific structure described above. If necessary, the aforementioned layers may be omitted or added. This application does not impose any particular limitation on the thickness of the aforementioned layers, as long as the purpose of this application can be achieved. For example, the organic electroluminescent device may sequentially include, on a substrate, an anode (100nm to 150nm), a hole injection layer (5nm to 20nm), a hole transport layer (80nm to 140nm), an electron blocking layer (5nm to 15nm), a light-emitting layer (20nm to 45nm), a hole blocking layer (5nm to 15nm), an electron transport layer (30nm to 40nm), an electron injection layer (3nm to 10nm), a cathode (100nm to 160nm), and a light extraction layer (50nm to 90nm). For example, Figure 1 A schematic diagram of a typical organic electroluminescent device 10 is shown, wherein, from bottom to top, a substrate 11, a reflective anode 12, a hole injection layer 13, a hole transport layer 14, a light-emitting layer 15, an electron transport layer 16, an electron injection layer 17, and a cathode 18 are arranged sequentially.

[0048] In some other embodiments of this application, the organic electroluminescent device of this application can be a top-emitting structure, which may include, on a substrate, an anode, a first hole injection layer, a first light-emitting unit, a charge generation layer, a second hole injection layer, a second light-emitting unit, an electron injection layer, and a transparent or semi-transparent cathode in sequence. The organic electroluminescent device of this application can also be a bottom-emitting structure, which may include, on a substrate, a transparent or semi-transparent anode, a first hole injection layer, a first light-emitting unit, a charge generation layer, a second hole injection layer, a second light-emitting unit, an electron injection layer, and a cathode structure in sequence. The organic electroluminescent device of this application can also be a dual-sided light-emitting structure, which may include, on a substrate, a transparent or semi-transparent anode, a first hole injection layer, a first light-emitting unit, a charge generation layer, a second hole injection layer, a second light-emitting unit, an electron injection layer, and a transparent or semi-transparent cathode structure in sequence. The first light-emitting unit includes a first hole transport layer, a first light-emitting layer, and a first electron transport layer arranged sequentially, and the second light-emitting unit includes a second hole transport layer, a second light-emitting layer, and a second electron transport layer arranged sequentially.

[0049] For example, an organic electroluminescent device may sequentially comprise, on a substrate, an anode (100nm to 150nm) made of metal, a first hole injection layer (5nm to 20nm), a first hole transport layer (80nm to 140nm), a first light-emitting layer (20nm to 45nm), a first electron transport layer (30nm to 40nm), a charge generation layer (5nm to 20nm), a second hole injection layer (5nm to 20nm), a second hole transport layer (80nm to 140nm), a second light-emitting layer (20nm to 45nm), a second electron transport layer (30nm to 40nm), an electron injection layer (3nm to 10nm), a cathode (100nm to 160nm), and a light extraction layer (50nm to 90nm). Exemplarily, Figure 2 A schematic diagram of another 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 23a, a first hole transport layer 24a, a first light-emitting layer 25a, a first electron transport layer 26a, a charge generation layer 29, a second hole injection layer 23b, a second hole transport layer 24b, a second light-emitting layer 25b, a second electron transport layer 26b, an electron injection layer 27, and a cathode 28 are arranged sequentially.

[0050] Understandable. Figure 1 and Figure 2 The structures of two typical organic electroluminescent devices are shown only schematically. This application is not limited to these structures. The electron transport materials and / or charge generation materials of this application can be used in any type of organic electroluminescent device.

[0051] For convenience, the organic electroluminescent devices of this application are illustrated below, but this does not imply any limitation on the scope of protection of this application. It is understood that all organic electroluminescent devices capable of using the electron transport materials and / or charge generating materials of this application are within the scope of protection of this application.

[0052] In this application, the substrate is not particularly limited and conventional substrates used in organic electroluminescent devices in the prior art can be used, such as glass, polymer materials, and glass and polymer materials with thin-film transistor (TFT) components.

[0053] In this application, the material of the aforementioned reflective anode is not particularly limited. It 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), and zinc oxide (ZnO), or metallic materials such as silver and its alloys, aluminum and its alloys, or organic conductive materials such as poly(3,4-ethylenedioxythiophene) (PEDOT). Alternatively, the reflective anode may be a multilayer structure formed from the aforementioned materials. This application does not particularly limit the number of layers in the multilayer structure. The number of layers can be selected according to actual needs, as long as it meets the purpose of this application. For example, one layer, two layers, three layers, or more layers.

[0054] In this application, there are no particular limitations on the material of the hole injection layer. Hole injection layer materials known in the art can be used, such as hole transport material (HTM) as the hole injection material.

[0055] In this application, the hole injection layer may further include a p-type dopant. There are no particular limitations on the type of p-type dopant; various p-type dopants known in the art can be used, such as:

[0056]

[0057] In this application, there is no particular limitation on the amount of p-type dopant used, and it can be any amount known to those skilled in the art.

[0058] In this application, the material of the hole transport layer is not particularly limited and can be made of hole transport materials (HTM) known in the art. The number of hole transport layers is not particularly limited and can be adjusted according to actual needs, as long as it meets the purpose of this application, for example, 1 layer, 2 layers, 3 layers, 4 layers or more.

[0059] For example, the materials used for the hole injection layer and the materials used for the hole transport layer may be selected from, but are not limited to, at least one of the following HT-1 to HT-31 compounds:

[0060]

[0061]

[0062] In this application, the material of the light-emitting layer includes a main material and a guest material. There are no particular restrictions on the amount of the main material and the guest material, and the amounts can be those known to those skilled in the art.

[0063] In this application, the host material of the luminescent layer is not particularly limited, and at least one of the red luminescent layer host materials known in the art can be used. For example, at least one of the following RH-1 to RH-13 compounds can be selected:

[0064]

[0065] The host material for the luminescent layer can also be at least one of the green luminescent layer host materials known in the art. For example, it can be selected from, but is not limited to, at least one of the following GPH-1 to GPH-80 compounds:

[0066]

[0067]

[0068]

[0069]

[0070] The host material for the luminescent layer can also be at least one of the blue luminescent layer host materials known in the art. For example, it can be at least one of the following compounds, but not limited to: BH-1 to BH-10.

[0071]

[0072] The luminescent layer guest material can be a red luminescent layer guest material, for example, it can be selected from, but is not limited to, at least one of the following RPD-1 to RPD-28 compounds:

[0073]

[0074] The luminescent layer guest material can be a green luminescent layer guest material, for example, it can be selected from at least one of the following GD01 to GD04 compounds:

[0075]

[0076] The luminescent layer guest material can be a blue luminescent layer guest material, for example, it can be selected from, but is not limited to, at least one of the following BD-1 to BD-9 compounds:

[0077]

[0078] In this application, the aforementioned electron transport layer may include at least one of the electron transport materials of this application, or may include a combination of at least one of the electron transport materials of this application and at least one of the following known electron transport materials.

[0079] For example, known electron transport materials may be selected from, but are not limited to, at least one of the following ET-1 to ET-57 compounds:

[0080]

[0081]

[0082]

[0083]

[0084] In this application, the electron transport layer may further include an n-type dopant. There are no particular limitations on the type of n-type dopant; various n-type dopants known in the art can be used, such as the following n-type dopants:

[0085]

[0086] In this application, there is no particular limitation on the amount of n-type dopant used, and it can be any amount known to those skilled in the art.

[0087] In this application, the charge generation layer may contain at least one of the charge generation materials of this application, or may contain a combination of at least one of the charge generation materials of this application and at least one of the following known charge generation materials.

[0088] For example, known charge-generating materials may be selected from, but are not limited to, at least one of the following CGL00R1 to CGL00R4 compounds:

[0089]

[0090] In this application, the charge-generating layer may further include at least one of the following metals: Li and Yb.

[0091] In this application, there are no particular restrictions on the amount of metal used, and the amount can be known to those skilled in the art.

[0092] In this application, there are no particular limitations on the material of the electron injection layer. Electron injection materials known in the art can be used, such as at least one of the following materials in the prior art, including but not limited to lithium 8-hydroxyquinoline (LiQ), LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, and Ca.

[0093] In this application, the material of the cathode is not particularly limited and can be selected from, but is not limited to, magnesium-silver mixtures, LiF / Al, ITO, Al and other metals and oxides.

[0094] This application does not impose any particular limitation on the fabrication method of the organic electroluminescent device; any method known in the art can be used, including but not limited to the following steps:

[0095] (1) Clean the reflective anode on the substrate of the top-emitting organic electroluminescent device. In the cleaning machine, the device is subjected to chemical washing, water washing, brushing, high-pressure water washing, air knife and other steps, and then heat treatment.

[0096] (2) Hole injection material is vacuum-deposited on the reflective anode as a hole injection layer;

[0097] (3) Hole transport material is vacuum-deposited on the hole injection layer as a hole transport layer;

[0098] (4) A light-emitting layer is vacuum-deposited on the hole transport layer, the light-emitting layer containing a host material and a guest material;

[0099] (5) Vacuum evaporation of electron transport material on the light-emitting layer as an electron transport layer;

[0100] (6) Vacuum evaporation of electron injection material on the electron transport layer as an electron injection layer;

[0101] (7) Vacuum evaporation of cathode material on the electron injection layer as the cathode.

[0102] The method for fabricating organic electroluminescent devices in this application may also include, but is not limited to, the following steps:

[0103] (1) Clean the reflective anode on the substrate of the top-emitting organic electroluminescent device. In the cleaning machine, the device is subjected to chemical washing, water washing, brushing, high-pressure water washing, air knife and other steps, and then heat treatment.

[0104] (2) A hole injection material is vacuum-deposited on the reflective anode as the first hole injection layer;

[0105] (3) Vacuum evaporation of hole transport material on the first hole injection layer serves as the first hole transport layer;

[0106] (4) A first light-emitting layer is vacuum-deposited on the first hole transport layer, the light-emitting layer containing a host material and a guest material;

[0107] (5) Vacuum evaporation of electron transport material on the first light-emitting layer serves as the first electron transport layer;

[0108] (6) Vacuum evaporation of a charge-generating material on the first electron transport layer as a charge-generating layer;

[0109] (7) Vacuum vapor deposition of hole injection material on the charge generation layer as a second hole injection layer;

[0110] (8) Vacuum evaporation of hole transport material on the second hole injection layer serves as the second hole transport layer;

[0111] (9) A second light-emitting layer is vacuum-deposited on the second hole transport layer, the light-emitting layer containing a host material and a guest material;

[0112] (10) Vacuum evaporation of electron transport material on the second light-emitting layer serves as the second electron transport layer;

[0113] (11) Vacuum evaporation of electron injection material on the second electron transport layer as an electron injection layer;

[0114] (12) Vacuum evaporation of cathode material on the electron injection layer as the cathode.

[0115] A sixth aspect of this application provides a display device including the aforementioned organic electroluminescent device. Therefore, the display device provided by this application has excellent display performance. The display device may include, but is not limited to, monitors, televisions, tablet computers, mobile communication terminals, etc.

[0116] There are no particular limitations on the synthesis method of the compounds in this application; any method known to those skilled in the art can be used for synthesis. The following examples illustrate the synthesis process of the compounds in this application.

[0117] Synthesis Examples

[0118] Synthesis Example 1: Synthesis of Compound A1

[0119]

[0120] 100 mmol of 2-bromophenanthroline, 100 mmol of p-chlorophenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 ml of tetrahydrofuran (THF), and 200 ml of water were added to a reaction flask, along with 1 mol% of tetra(triphenylphosphine)palladium (Pd(PPh3)4). The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder M1. The amount of Pd(PPh3)4 added was 1 mol% of 2-bromophenanthroline.

[0121] 100 mmol of M1, 100 mmol of pinacol diborate, 41.4 g of potassium carbonate (300 mmol), and 800 ml of dioxane were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 100 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M2. The amount of Pd(PPh3)4 added was 1 mol% of M1.

[0122] 100 mmol of 2,9-dichlorophenanthroline, 100 mmol of 3-pyridineboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF, and 200 ml of water were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder M3. The amount of Pd(PPh3)4 added was 1 mol% of 2,9-dichlorophenanthroline.

[0123] 100 mmol of M2, 100 mmol of M3, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF, and 200 ml of water were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, Al. The amount of Pd(PPh3)4 added was 1 mol% of M2.

[0124] 1H NMR(400MHz,Chloroform)9.63(s,1H),8.97–8.66(m,5H),8.39(t,J=10.0Hz,2 H),8.04–7.84(m,4H),7.63–7.53(m,4H),7.50(s,1H),7.40(d,J=10.0Hz,4H).

[0125] Synthesis Example 2: Synthesis of Compound A4

[0126]

[0127] 100 mmol of 5-chlorophenanthroline, 100 mmol of p-chlorophenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF, and 200 ml of water were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder M1. The amount of Pd(PPh3)4 added was 1 mol% of 5-chlorophenanthroline.

[0128] 100 mmol of M1, 100 mmol of pinacol diborate, 41.4 g of potassium carbonate (300 mmol), and 800 ml of dioxane were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 100 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M2. The amount of Pd(PPh3)4 added was 1 mol% of M1.

[0129] 100 mmol of p-bromoiodobenzene, 100 mmol of 3-pyridineboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF, and 200 ml of water were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder M3. The amount of Pd(PPh3)4 added was 1 mol% of p-bromoiodobenzene.

[0130] 100 mmol of M3, 100 mmol of pinacol diborate, 41.4 g of potassium carbonate (300 mmol), and 800 ml of dioxane were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 100 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M4. The amount of Pd(PPh3)4 added was 1 mol% of M3.

[0131] 100 mmol of 2,9-dichlorophenanthroline, 100 mmol of M4, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF, and 200 ml of water were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M5. The amount of Pd(PPh3)4 added was 1 mol% of 2,9-dichlorophenanthroline.

[0132] 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 to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder A4. The amount of Pd(PPh3)4 added was 1 mol% of M2.

[0133] 1 H NMR(400MHz,Chloroform)9.24(s,1H),8.80(s,1H),8.72–8.65(m,4H),8.36(d,J=10.0Hz,3 H), 8.11 (d, J = 10.0Hz, 2H), 7.90 (d, J = 8.0Hz, 3H), 7.58-7.39 (m, 7H), 7.33 (d, J = 10.0Hz, 4H).

[0134] Synthesis Example 3: Synthesis of Compound A6:

[0135]

[0136] 100 mmol of 3-bromophenanthroline, 100 mmol of p-chlorophenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF, and 200 ml of water were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder M1. The amount of Pd(PPh3)4 added was 1 mol% of 3-bromophenanthroline.

[0137] 100 mmol of M1, 100 mmol of pinacol diborate, 41.4 g of potassium carbonate (300 mmol), and 800 ml of dioxane were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 100 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M2. The amount of Pd(PPh3)4 added was 1 mol% of M1.

[0138] 100 mmol of pyrazinamide, 100 mmol of phenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF, and 200 ml of water were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder M3. The amount of Pd(PPh3)4 added was 1 mol% of the pyrazinamide.

[0139] 100 mmol of M3, 100 mmol of p-chlorophenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF, and 200 ml of water were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M4. The amount of Pd(PPh3)4 added was 1 mol% of M3.

[0140] 100 mmol of M4, 100 mmol of pinacol diborate, 41.4 g of potassium carbonate (300 mmol), and 800 ml of dioxane were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 100 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M5. The amount of Pd(PPh3)4 added was 1 mol% of M4.

[0141] 100 mmol of 2,9-dichlorophenanthroline, 100 mmol of M5, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF, and 200 ml of water were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M6. The amount of Pd(PPh3)4 added was 1 mol% of 2,9-dichlorophenanthroline.

[0142] 100 mmol of M2, 100 mmol of M6, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF, and 200 ml of water were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, A6. The amount of Pd(PPh3)4 added was 1 mol% of M2.

[0143] 1 H NMR(400MHz,Chloroform)8.80(s,1H),8.44(d,J=8.4Hz,3H),8.44(s,1H),8.45–8.33(m,5H),8.27–8.09(m,4H),8 .24(d,J=12.0Hz,3H),8.09–7.86(m,6H),7.80(s,1H),7.57(d,J=10.0Hz,4H),7.49(d,J=8.0Hz,3H),7.25(s,1H).

[0144] Synthesis Example 4: Synthesis of Compound A7:

[0145]

[0146] 100 mmol of 4-chloro-2,9-dimethylphenanthroline, 100 mmol of m-chlorophenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF, and 200 ml of water were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder M1. The amount of Pd(PPh3)4 added was 1 mol% of 4-chloro-2,9-dimethylphenanthroline.

[0147] 100 mmol of M1, 100 mmol of pinacol diborate, 41.4 g of potassium carbonate (300 mmol), and 800 ml of dioxane were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 100 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M2. The amount of Pd(PPh3)4 added was 1 mol% of M1.

[0148] 100 mmol of p-bromoiodobenzene, 100 mmol of 3-pyridineboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF, and 200 ml of water were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder M3. The amount of Pd(PPh3)4 added was 1 mol% of p-bromoiodobenzene.

[0149] 100 mmol of M3, 100 mmol of pinacol diborate, 41.4 g of potassium carbonate (300 mmol), and 800 ml of dioxane were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 100 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M4. The amount of Pd(PPh3)4 added was 1 mol% of M3.

[0150] 100 mmol of 2,9-dichlorophenanthroline, 100 mmol of M4, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF, and 200 ml of water were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M5. The amount of Pd(PPh3)4 added was 1 mol% of 2,9-dichlorophenanthroline.

[0151] 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 to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder A7. The amount of Pd(PPh3)4 added was 1 mol% of M2.

[0152] 1 H NMR(400MHz,Chloroform)9.24(s,1H),8.74–8.64(m,4H),8.36(d,J=10.0Hz,3H),8.06(s,1H),7.69(d ,J=8.0Hz,4H),7.63–7.44(m,3H),7.42(d,J=7.6Hz,2H),7.36–7.09(m,5H),2.76(s,3H),2.69(s,3H).

[0153] Synthesis Example 5: Synthesis of Compound A13:

[0154]

[0155] 100 mmol of 3,8-dibromo-phenanthroline, 100 mmol of phenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF, and 200 ml of water were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder M1. The amount of Pd(PPh3)4 added was 1 mol% of 3,8-dibromo-phenanthroline.

[0156] 100 mmol of M1, 100 mmol of p-chlorophenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF, and 200 ml of water were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M2. The amount of Pd(PPh3)4 added was 1 mol% of M1.

[0157] 100 mmol of M2, 100 mmol of pinacol diborate, 41.4 g of potassium carbonate (300 mmol), and 800 ml of dioxane were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 100 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M3. The amount of Pd(PPh3)4 added was 1 mol% of M2.

[0158] 100 mmol of p-chlorophenylboronic acid, 100 mmol of 2-bromoquinoline, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF, and 200 ml of water were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M4. The amount of Pd(PPh3)4 added was 1 mol% of the p-chlorophenylboronic acid.

[0159] 100 mmol of M4, 100 mmol of pinacol diborate, 41.4 g of potassium carbonate (300 mmol), and 800 ml of dioxane were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 100 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M5. The amount of Pd(PPh3)4 added was 1 mol% of M4.

[0160] 100 mmol of 2,9-dichlorophenanthroline, 100 mmol of M5, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF, and 200 ml of water were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M6. The amount of Pd(PPh3)4 added was 1 mol% of 2,9-dichlorophenanthroline.

[0161] 100 mmol of M3, 100 mmol of M6, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF, and 200 ml of water were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, Al3. The amount of Pd(PPh3)4 added was 1 mol% of M3.

[0162] 1 H NMR(400MHz,Chloroform)9.46(s,1H),8.53(s,1H),8.33(d,J=8.0Hz,4H),8.10(s,1H),7.89(d,J=10 .0Hz,4H),7.80(s,1H),7.77(d,J=8.4Hz,6H),7.61(d,J=10.0Hz,4H),7.56–7.39(m,8H),7.34(s,1H).

[0163] Synthesis Example 6: Synthesis of Compound A20:

[0164]

[0165] 100 mmol of 2,9-dichlorophenanthroline, 100 mmol of phenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF, and 200 ml of water were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder M1. The amount of Pd(PPh3)4 added was 1 mol% of 2,9-dichlorophenanthroline.

[0166] 100 mmol of M1, 100 mmol of p-chlorophenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF, and 200 ml of water were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M2. The amount of Pd(PPh3)4 added was 1 mol% of M1.

[0167] 100 mmol of M2, 100 mmol of pinacol diborate, 41.4 g of potassium carbonate (300 mmol), and 800 ml of dioxane were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 100 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M3. The amount of Pd(PPh3)4 added was 1 mol% of M2.

[0168] 100 mmol of p-bromoiodobenzene, 100 mmol of 3-pyridineboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF, and 200 ml of water were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M4. The amount of Pd(PPh3)4 added was 1 mol% of p-bromoiodobenzene.

[0169] 100 mmol of M4, 100 mmol of pinacol diborate, 41.4 g of potassium carbonate (300 mmol), and 800 ml of dioxane were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 100 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M5. The amount of Pd(PPh3)4 added was 1 mol% of M4.

[0170] 100 mmol of 2,9-dichlorophenanthroline, 100 mmol of M5, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF, and 200 ml of water were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M6. The amount of Pd(PPh3)4 added was 1 mol% of 2,9-dichlorophenanthroline.

[0171] 100 mmol of M3, 100 mmol of M6, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF, and 200 ml of water were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, A20. The amount of Pd(PPh3)4 added was 1 mol% of M3.

[0172] 1 H NMR (400MHz, Chloroform) 9.39 (s, 1H), 8.34 (t, J = 8.4Hz, 4H), 8.01 (s, 2H), 7.94–7.66 (m, 6H), 7.60–7.52 (m, 9H), 7.52 (s, 1H), 7.41 (d, J = 10.0Hz, 6H).

[0173] Other compounds in this application can be synthesized by selecting suitable raw materials according to the ideas in Synthesis Examples 1-6 above, or by selecting any other suitable methods and raw materials.

[0174] Example 1

[0175] The glass plate coated with a 150nm 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 all moisture was removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam.

[0176] Then, the glass substrate with the reflective anode was placed in a vacuum chamber and evacuated to a vacuum level of less than 10. -5A hole injection layer with a thickness of 10 nm is vacuum-deposited on the aforementioned reflective anode layer film. The hole injection layer material includes hole injection layer material HT-11 and p-type dopant p-1. The deposition is performed using a multi-source co-evaporation method. The deposition rate of hole injection layer material HT-11 is adjusted to 0.1 nm / s, and the deposition rate of p-type dopant p-1 is 3% of the deposition rate of hole injection layer material HT-11. The deposition film thickness is 10 nm.

[0177] Then, a hole transport layer with a thickness of 80 nm is vacuum-deposited on top of the hole injection layer, wherein the hole transport material is HT-5 and the deposition rate is 0.1 nm / s.

[0178] Then, a light-emitting layer with a thickness of 30 nm is vacuum-deposited on the hole transport layer. The light-emitting layer includes host material BH-2 and guest material BD-1. The deposition is carried out using a multi-source co-evaporation method, wherein the deposition rate of host material BH-2 is adjusted to 0.1 nm / s, and the deposition rate of guest material BD-1 is 3% of the deposition rate of host material BH-2.

[0179] Then, an electron transport layer with a thickness of 30 nm is vacuum-deposited on the light-emitting layer. The electron transport material is compound Al, and the deposition rate is 0.1 nm / s.

[0180] Then, a 5 nm thick LiF layer was vacuum-deposited on the electron transport layer as an electron injection layer, with a deposition rate of 0.1 nm / s.

[0181] Finally, an Al layer with a thickness of 150 nm was vacuum-deposited on the electron injection layer as the cathode of the organic electroluminescent device, wherein the deposition rate was 0.1 nm / s.

[0182] Examples 2-6

[0183] Except that compound A1 was replaced by compounds A4, A6, A7, A13, and A20 in sequence, the rest was the same as in Example 1.

[0184] Example 7

[0185] The glass plate coated with a 150nm 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 all moisture was removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam.

[0186] Then, the glass substrate with the reflective anode was placed in a vacuum chamber and evacuated to a vacuum level of less than 10. -5A first hole injection layer with a thickness of 10 nm is vacuum-deposited on the aforementioned reflective anode layer film. The material of the first hole injection layer includes hole injection layer material HT-11 and p-type dopant p-1. The deposition is performed using a multi-source co-evaporation method. The deposition rate of hole injection layer material HT-11 is adjusted to 0.1 nm / s, and the deposition rate of p-type dopant p-1 is 3% of the deposition rate of hole injection layer material HT-11. The thickness of the deposited film is 10 nm.

[0187] Then, a first hole transport layer with a thickness of 80 nm is vacuum-deposited on the first hole injection layer, wherein the hole transport material is HT-5 and the deposition rate is 0.1 nm / s.

[0188] Then, a first light-emitting layer with a thickness of 30 nm is vacuum-deposited on the first hole transport layer. The first light-emitting layer includes a host material BH-2 and a guest material BD-1. The deposition is carried out using a multi-source co-evaporation method, wherein the deposition rate of the host material BH-2 is adjusted to 0.1 nm / s, and the deposition rate of the guest material BD-1 is 3% of the deposition rate of the host material BH-2.

[0189] Then, a first electron transport layer with a thickness of 30 nm is vacuum-deposited on the first light-emitting layer. The electron transport material is compound ET-6, and the deposition rate is 0.1 nm / s.

[0190] The first hole transport layer, the first light-emitting layer, and the first electron transport layer are used as the first light-emitting unit.

[0191] A charge generation layer with a thickness of 10 nm is vacuum-deposited on the first light-emitting unit. The material of the charge generation layer includes Al compound and metal Yb, wherein the deposition rate of Al compound is 0.1 nm / s, and the deposition rate ratio of Al compound to metal Yb is 99:1.

[0192] Then, a second hole injection layer with a thickness of 10 nm is deposited on the charge generation layer. The material of the second hole injection layer includes hole injection layer material HT-11 and p-type dopant p-1. The evaporation rate of hole injection layer material HT-11 is adjusted to 0.1 nm / s, and the evaporation rate ratio of hole injection layer material HT-11 to p-type dopant p-1 is 99:1.

[0193] A second hole transport layer with a thickness of 80 nm is vacuum-deposited on the second hole injection layer, wherein the hole transport material is HT-5 and the deposition rate is 0.1 nm / s.

[0194] Then, a second light-emitting layer with a thickness of 30 nm is vacuum-deposited on the second hole transport layer. The second light-emitting layer includes a host material BH-2 and a guest material BD-1. The deposition is carried out using a multi-source co-evaporation method, wherein the deposition rate of the host material BH-2 is adjusted to 0.1 nm / s, and the deposition rate of the guest material BD-1 is 3% of the deposition rate of the host material BH-2.

[0195] Then, a second electron transport layer with a thickness of 30 nm is vacuum-deposited on the second light-emitting layer. The electron transport material is compound ET-6, and the deposition rate is 0.1 nm / s.

[0196] The aforementioned second hole transport layer, second light-emitting layer, and second electron transport layer are used as the second light-emitting unit.

[0197] Then, a 5 nm thick LiF layer is vacuum-deposited on the second electron transport layer of the second light-emitting unit as an electron injection layer, wherein the deposition rate is 0.1 nm / s.

[0198] Finally, an Al layer with a thickness of 150 nm was vacuum-deposited on the electron injection layer as the cathode of the organic electroluminescent device, wherein the deposition rate was 0.1 nm / s.

[0199] Examples 8-12

[0200] Except for replacing compound A1 with compounds A4, A6, A7, A13, and A20 in sequence, the rest is the same as in Example 7.

[0201] Comparative Example 1

[0202] Except for replacing compound A1 with electron transport material ET-6, the rest is the same as in Example 1.

[0203] Comparative Example 2

[0204] Except for replacing compound A1 with charge-generating material CGL00R1, the rest is the same as in Example 7.

[0205] The organic electroluminescent devices prepared by the above process were subjected to the following performance tests:

[0206] Under the same brightness, the driving voltage, current efficiency, and lifetime of the organic electroluminescent devices prepared in Examples 1-12 and Comparative Examples 1-2 were measured using a digital source meter and a luminance meter. Specifically, the voltage was increased at a rate of 0.1V per second, and the measurement was performed when the brightness of the organic electroluminescent device reached 1000 cd / m². 2The voltage at that time is the driving voltage, and the current density at that time is also measured; the ratio of brightness to current density is the current efficiency. The LT95's lifespan test is as follows: using a luminance meter at 1000 cd / m²... 2 At a constant current, the brightness of the organic electroluminescent device decreased to 950 cd / m² under the specified brightness. 2 The time is expressed in hours (h).

[0207] The parameters and performance test results of each embodiment and comparative example are shown in Table 1 and Table 2.

[0208] Table 1

[0209] Electron transport materials <![CDATA[Required brightness cd / m 2 > Drive voltage V Current efficiency cd / A Lifespan (LT95)h Example 1 A1 1000.00 3.5 7.9 113 Example 2 A4 1000.00 3.6 8.0 110 Example 3 A6 1000.00 3.7 7.8 112 Example 4 A7 1000.00 3.6 8.0 114 Example 5 A13 1000.00 3.7 7.9 118 Example 6 A20 1000.00 3.8 8.0 116 Comparative Example 1 ET-6 1000.00 4.0 7.2 107

[0210] Table 2

[0211]

[0212]

[0213] As shown in Table 1, compounds A1, A4, A6, A7, A13, and A20 obtained in this application, when used as electron transport materials in organic electroluminescent devices, can effectively reduce the driving voltage, improve current efficiency, and extend the device lifespan compared to Comparative Example 1. This demonstrates that the compounds provided in this application, when used as electron transport materials in organic electroluminescent devices, exhibit significant performance improvements, particularly in enhancing luminous efficiency and extending lifespan, making them high-performance electron transport materials.

[0214] As shown in Table 2, compounds A1, A4, A6, A7, A13, and A20 obtained in this application, when used as charge-generating materials in organic electroluminescent devices, can effectively reduce the driving voltage, improve current efficiency, and extend the device's lifespan compared to Comparative Example 2. This demonstrates that the compounds provided in this application, when used as charge-generating materials in organic electroluminescent devices, exhibit significant performance improvements, particularly in enhancing luminous efficiency and extending lifespan, making them high-performance charge-generating materials.

[0215] It is understood that the organic electroluminescent devices in Examples 1-12 are blue organic electroluminescent devices, and the above examples are only examples. The compounds provided in this application can be used as electron transport materials and / or charge generation materials, and can also be applied to red organic electroluminescent devices and green organic electroluminescent devices to reduce the driving voltage of red organic electroluminescent devices and green organic electroluminescent devices, improve their luminous efficiency, and extend their service life.

[0216] It should be noted that, in this document, the terms "comprising," "including," or any other variations thereof are intended to cover non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements includes not only those elements but also other elements not expressly listed, or elements inherent to such a process, method, article, or apparatus. Unless otherwise specified, an element defined by the phrase "comprising one..." does not exclude the presence of other identical elements in the process, method, article, or apparatus that includes said element.

[0217] The various embodiments in this specification are described in a related manner. The same or similar parts between the various embodiments can be referred to each other. Each embodiment focuses on describing the differences from other embodiments.

[0218] The above description is merely a preferred embodiment of this application and is not intended to limit the scope of protection of this application. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of this application are included within the scope of protection of this application.

Claims

1. A compound having the structural formula shown in (I): ； in, L 1 Selected from chemical bonds, unsubstituted or Rc-substituted C6-C 30 Alpha-aryl, L 2 Selected from the unsubstituted subunits of the following compounds: benzene, biphenyl, phenylpyridine; X 1 -X 5 Each is independently selected from CR or N, and X 1 -X 5 At least one of N is selected from N, and R is selected from hydrogen, deuterium, C1-C4 alkyl, C2-C6 alkenyl, unsubstituted C6-C 18 Aryl, when X 1 -X 5 When there are multiple selections from CR, the R values ​​in each CR may be the same or different; Q is selected from or Any one of the following, and the hydrogen atoms in Q can be independently substituted by Ra, where Ra is selected from C1-C4 alkyl, unsubstituted or Rc-substituted C6-C 30 Aryl, unsubstituted or Rc-substituted C3-C 30 heteroaryl, L 2 Connect to any connectable position in Q; The heteroatoms in the heteroaryl group are each independently selected from O, S, and N; The substituents Rc of each group are independently selected from deuterium, halogen, nitro, cyano, C1-C4 alkyl, phenyl, biphenyl, terphenyl, and naphthyl.

2. The compound according to claim 1, wherein, L 1 Selected from chemical bonds, unsubstituted or Rc-substituted C6-C 18 Alpha-aryl; L 2 Selected from the unsubstituted subunits of the following compounds: benzene, biphenyl, phenylpyridine; Ra is selected from C1-C4 alkyl groups, unsubstituted or Rc-substituted C6-C groups. 18 Aryl, unsubstituted or Rc-substituted C3-C 12 Mixed aromatics; R is selected from hydrogen, deuterium, C1-C4 alkyl, C2-C4 alkenyl, and unsubstituted C6-C. 18 Aryl.

3. The compound according to claim 1, wherein, The Ra is selected from methyl, ethyl, unsubstituted or Rc-substituted groups of the following: phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, pyridyl, pyridinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, cyclolinyl, naphthinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, benzothiophene, dibenzothiophene, aza-dibenzothiophene.

4. The compound according to claim 1, wherein, The L 1 Subunits selected from the following compounds that are chemically bonded, unsubstituted, or Rc-substituted: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene; The L 2 Selected from the unsubstituted subunits of the following compounds: benzene, biphenyl, phenylpyridine.

5. The compound according to claim 1, wherein, Each of the R groups is independently selected from hydrogen, deuterium, methyl, ethyl, vinyl, and the following unsubstituted groups: phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, and triphenylene.

6. The compound according to claim 1, wherein, The compound is selected from the following compounds: 。 7. Use of a compound according to any one of claims 1-6 as a functional layer material for an organic electroluminescent device.

8. The use according to claim 7, wherein, The functional layer is selected from at least one of the electron transport layer and the charge generation layer.

9. An electron transport material comprising at least one of the compounds according to any one of claims 1-6.

10. A charge-generating material comprising at least one of the compounds according to any one of claims 1-6.

11. An organic electroluminescent device comprising at least one of the electron transport material of claim 9 and / or the charge generating material of claim 10.

12. A display device comprising the organic electroluminescent device of claim 11.

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