A compound, a light-emitting layer host material and an organic electroluminescence device

Abstract

The application provides a compound shown in formula (I) and a light-emitting layer host material, an organic electroluminescent device and a display device comprising the same. The compound has high stability and good film-forming property. The compound introduces electron-donating and electron-withdrawing groups, can balance the hole and electron transport properties as a bipolar light-emitting layer host material, simplifies the device structure, is conducive to the preparation of the organic electroluminescent device, and improves the luminous efficiency and service life of the organic electroluminescent device. The organic electroluminescent device provided by the application comprises the compound as a light-emitting layer host material, has lower driving voltage, better luminous efficiency and longer service life. The display device provided by the application has excellent display effect.

Description

Technical Field

[0001] This application relates to the field of organic light-emitting display technology, and in particular to a compound, a host material for a light-emitting layer, and an organic electroluminescent device. Background Technology

[0002] Human and societal development is inseparable from light, especially luminescent materials. Luminescent materials are divided into inorganic and organic luminescent materials. Compared to inorganic luminescent materials, organic luminescent materials are favored by researchers due to their greater variety, easily tunable emission wavelengths, and relatively flexible molecular design. In recent years, with the advancement of science and technology, organic electroluminescent (OLED) devices have gradually entered the market due to their advantages such as fast response speed, high luminous efficiency, and wide viewing angle. OLED devices consist of a substrate, cathode, anode, hole injection layer, electron injection layer, hole transport layer, electron transport layer, electron blocking layer, hole blocking layer, and luminescent layer. Among these, the luminescent layer is the core component of OLED devices, playing a crucial role in their performance and lifespan. Therefore, designing and synthesizing highly efficient luminescent layer materials has become a major research focus. Summary of the Invention

[0003] The purpose of this application is to provide a compound that, when used as the host material of the light-emitting layer, can improve the luminous efficiency and extend the lifespan of organic electroluminescent devices.

[0004] The first aspect of this application provides a compound of formula (I):

[0005]

[0006] Among them, R 1 -R 5 Each is independently selected from hydrogen, deuterium, C1-C6 alkyl, unsubstituted or Ra-substituted C1-C6 alkenyl, unsubstituted or Ra-substituted C6-C 30 Aryl, unsubstituted or Ra-substituted C3-C 30 heteroaryl, R 1 and R 2 They can be connected to form a loop, R 3 and R 5 They can be connected to form a ring;

[0007] A is selected from unsubstituted or Ra-substituted C6-C. 30 Aryl, unsubstituted or Ra-substituted C3-C 18 Mixed aromatics;

[0008] B is selected from C3-C 10 Cycloalkyl, unsubstituted or Ra-substituted C6-C 30Aryl, unsubstituted or Ra-substituted C3-C 18 Mixed aromatics;

[0009] X 1 Selected from CR 6 Or N, R 6 Selected from hydrogen, deuterium, C1-C6 alkyl, unsubstituted or Ra-substituted C6-C 30 Aryl, unsubstituted or Ra-substituted C3-C 18 heteroaryl, R 6 A and B can be connected to form a loop;

[0010] X 2 Selected from CR 7 R 8 O or SO2, R 7 and R 8 Each is independently selected from hydrogen, deuterium, C1-C6 alkyl, unsubstituted or Ra-substituted C6-C 30 Aryl, unsubstituted or Ra-substituted C3-C 30 heteroaryl, R 7 and R 8 They can be connected to form a ring;

[0011] L is selected from the C6-C bonds that are either chemically bonded, unsubstituted, or substituted by Ra. 30 aryl, unsubstituted or Ra-substituted C3-C 30 heteroaryl;

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

[0013] Each of the Ra groups is independently selected from deuterium, halogen, nitro, cyano, C1-C4 alkyl, phenyl, biphenyl, naphthyl, C1-C4 haloalkyl, quinoxalinyl, quinolinyl, pyridinyl, or benzofuranyl.

[0014] A second aspect of this application provides a light-emitting layer host material comprising at least one of the compounds provided in the first aspect of this application.

[0015] A third aspect of this application provides an organic electroluminescent device comprising at least one of the light-emitting layer host materials provided in the second aspect of this application.

[0016] A fourth aspect of this application provides a display device that includes the organic electroluminescent device provided in the third aspect of this application.

[0017] The compounds provided in this application exhibit high stability and good film-forming properties. By introducing electron-donating and electron-withdrawing groups into these compounds, they serve as the host material for a bipolar light-emitting layer, balancing the characteristics of hole and electron transport, simplifying the device structure, facilitating the fabrication of organic electroluminescent devices, and improving the luminous efficiency and lifespan of organic electroluminescent devices. The organic electroluminescent devices provided in this application, incorporating the compounds of this application as the host material for the light-emitting layer, exhibit lower driving voltage, better luminous efficiency, and longer lifespan. The display devices provided in this application demonstrate excellent display performance.

[0018] 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

[0019] To more clearly illustrate the technical solutions in the embodiments of this application, the accompanying drawings used in the description of the embodiments will be briefly introduced below. Obviously, the accompanying drawings described below are only some embodiments of this application. For those skilled in the art, other embodiments can be obtained based on these accompanying drawings.

[0020] Figure 1 This is a schematic diagram of a typical organic electroluminescent device. Detailed Implementation

[0021] 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. All other embodiments obtained by those skilled in the art based on this application are within the scope of protection of this application.

[0022] The first aspect of this application provides a compound of formula (I):

[0023]

[0024] Among them, R 1 -R 5 Each is independently selected from hydrogen, deuterium, C1-C6 alkyl, unsubstituted or Ra-substituted C1-C6 alkenyl, unsubstituted or Ra-substituted C6-C 30 Aryl, unsubstituted or Ra-substituted C3-C 30 heteroaryl, R 1 and R 2 They can be connected to form a loop, R 3 and R 5 They can be connected to form a ring;

[0025] A is selected from unsubstituted or Ra-substituted C6-C. 30Aryl, unsubstituted or Ra-substituted C3-C 18 Mixed aromatics;

[0026] B is selected from C3-C 10 Cycloalkyl, unsubstituted or Ra-substituted C6-C 30 Aryl, unsubstituted or Ra-substituted C3-C 18 Mixed aromatics;

[0027] X 1 Selected from CR 6 Or N, R 6 Selected from hydrogen, deuterium, C1-C6 alkyl, unsubstituted or Ra-substituted C6-C 30 Aryl, unsubstituted or Ra-substituted C3-C 18 heteroaryl, R 6 A and B can be connected to form a loop;

[0028] X 2 Selected from CR 7 R 8 O or SO2, R 7 and R 8 Each is independently selected from hydrogen, deuterium, C1-C6 alkyl, unsubstituted or Ra-substituted C6-C 30 Aryl, unsubstituted or Ra-substituted C3-C 30 heteroaryl, R 7 and R 8 They can be connected to form a ring;

[0029] L is selected from the C6-C bonds that are either chemically bonded, unsubstituted, or substituted by Ra. 30 aryl, unsubstituted or Ra-substituted C3-C 30 heteroaryl;

[0030] The heteroatoms on the heteroaryl group or the heteroalkylene group are each independently selected from N, O, and S;

[0031] Each of the Ra groups is independently selected from deuterium, halogen, nitro, cyano, C1-C4 alkyl, phenyl, biphenyl, naphthyl, C1-C4 haloalkyl, quinoxalinyl, quinolinyl, pyridinyl, or benzofuranyl.

[0032] Preferably, R 1 -R 5Each group is independently selected from hydrogen, deuterium, methyl, ethyl, propyl, vinyl, propenyl, butenyl, unsubstituted or Ra-substituted groups of the following compounds: benzene, biphenyl, naphthalene, phenanthrene, pyrene, fluorene, spirofluorene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, pyridopyrazine, triazine, furan, benzofuran, dibenzofuran, imidazole, benzimidazole, thiophene, benzothiophene, dibenzothiophene, 9,9-dimethylfluorene, aromatic amine, carbazole, quinazoline, benzothiazole, R 1 and R 2 They can be connected to form a loop, R 3 and R 5 They can be connected to form a ring.

[0033] Preferably, A is selected from the groups of the following compounds that are unsubstituted or substituted by Ra: benzene, biphenyl, naphthalene, phenanthrene, pyrene, fluorene, spirofluorene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, pyridopyrazine, triazine, furan, benzofuran, dibenzofuran, imidazole, benzimidazole, thiophene, benzothiophene, dibenzothiophene, 9,9-dimethylfluorene, aromatic amine, carbazole, quinazoline, benzothiazole.

[0034] Preferably, B is selected from cyclopropane, cyclobutane, cyclopentane, cyclohexane, and unsubstituted or Ra-substituted groups of the following compounds: benzene, biphenyl, naphthalene, phenanthrene, pyrene, fluorene, spirofluorene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, pyridopyrazine, triazine, furan, benzofuran, dibenzofuran, imidazole, benzimidazole, thiophene, benzothiophene, dibenzothiophene, 9,9-dimethylfluorene, aromatic amine, carbazole, quinazoline, benzothiazole.

[0035] Preferably, X 1 Selected from CR 6 Or N, R 6 Selected from hydrogen, deuterium, methyl, ethyl, propyl, unsubstituted or Ra-substituted groups of the following compounds: benzene, biphenyl, naphthalene, phenanthrene, pyrene, fluorene, spirofluorene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, pyridopyrazine, triazine, furan, benzofuran, dibenzofuran, imidazole, benzimidazole, thiophene, benzothiophene, dibenzothiophene, 9,9-dimethylfluorene, aromatic amine, carbazole, quinazoline, benzothiazole, R 6 A and A can be connected to form a loop.

[0036] Preferably, X 2 Selected from CR 7 R 8 O or SO2, R 7 and R 8Each group is independently selected from hydrogen, deuterium, methyl, ethyl, propyl, unsubstituted or Ra-substituted groups of the following compounds: benzene, phenol, biphenyl, naphthalene, phenanthrene, pyrene, fluorene, spirofluorene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, pyridopyrazine, triazine, furan, benzofuran, dibenzofuran, imidazole, benzimidazole, thiophene, benzothiophene, dibenzothiophene, 9,9-dimethylfluorene, aromatic amine, carbazole, quinazoline, benzothiazole, R 7 and R 8 They can be connected to form a ring.

[0037] Preferably, L is selected from the subunits of the following compounds that are chemically bonded, unsubstituted, or substituted by Ra: benzene, biphenyl, naphthalene, phenanthrene, pyrene, fluorene, spirofluorene, and imidazole.

[0038] Preferably, the halogen is selected from fluorine, chlorine or bromine; the C1-C4 haloalkyl is selected from C1-C4 fluoroalkyl, C1-C4 chloroalkyl or C1-C4 bromoalkyl.

[0039] Preferably, each of Ra is independently selected from deuterium, fluorine, chlorine, bromine, nitro, cyano, methane, ethane, propane, n-butane, isobutane, phenyl, biphenyl, naphthyl, monofluoromethane, monochloromethane, difluoromethane, dichloromethane, trifluoromethane, chloroform, quinoxalinyl, quinolinyl, pyridinyl, or benzofuranyl.

[0040] The compounds provided in this application have high stability and good film-forming properties. The introduction of electron-donating and electron-withdrawing groups into the compounds, as the main material of the bipolar light-emitting layer, can balance the characteristics of hole and electron transport, simplify the device structure, facilitate the preparation of organic electroluminescent devices, and improve the luminous efficiency and lifespan of organic electroluminescent devices.

[0041] In some embodiments of the first aspect of this application, the compound is a compound represented by formula (II):

[0042]

[0043] in,

[0044] R 3 -R 5 R 9 -R 12 Each is independently selected from hydrogen, deuterium, C1-C6 alkyl, unsubstituted or Ra-substituted C6-C 18 Aryl, unsubstituted or Ra-substituted C3-C 18 heteroaryl, R 3 and R 5 They can be connected to form a ring;

[0045] A is selected from unsubstituted or Ra-substituted C6-C. 30Aryl, unsubstituted or Ra-substituted C3-C 18 Mixed aromatics;

[0046] B is selected from C3-C6 cycloalkyl, unsubstituted or substituted by Ra, C6-C 18 Aryl, unsubstituted or Ra-substituted C3-C 18 Mixed aromatics;

[0047] L is selected from the C6-C bonds that are either chemically bonded, unsubstituted, or substituted by Ra. 18 aryl, unsubstituted or Ra-substituted C3-C 10 heteroaryl;

[0048] The heteroatoms on the heteroaryl group or the heteroalkylene group are each independently selected from N, O, and S;

[0049] Each of the Ra groups is independently selected from deuterium, halogen, nitro, cyano, C1-C4 alkyl, phenyl, biphenyl, naphthyl, C1-C4 haloalkyl, quinoxalinyl, quinolinyl, pyridinyl, or benzofuranyl.

[0050] Preferably, R 3 -R 5 R 9 -R 12 Each of the following groups, independently selected from hydrogen, deuterium, methyl, ethyl, propyl, unsubstituted or Ra-substituted, is selected from: benzene, biphenyl, naphthalene, phenanthrene, pyrene, fluorene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, pyridopyrazine, triazine, furan, benzofuran, dibenzofuran, imidazole, benzimidazole, thiophene, benzothiophene, dibenzothiophene, 9,9-dimethylfluorene, aromatic amine, carbazole, quinazoline, benzothiazole, R 3 and R 5 They can be connected to form a ring.

[0051] Preferably, A is selected from the following compounds that are unsubstituted or substituted by Ra: benzene, biphenyl, naphthalene, phenanthrene, pyrene, fluorene, spirofluorene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, pyridopyrazine, triazine, furan, benzofuran, dibenzofuran, imidazole, benzimidazole, thiophene, benzothiophene, dibenzothiophene, 9,9-dimethylfluorene, aromatic amine, carbazole, quinazoline, benzothiazole.

[0052] Preferably, B is selected from cyclopropane, cyclobutane, cyclopentane, cyclohexane, unsubstituted or Ra-substituted groups of the following compounds: benzene, biphenyl, naphthalene, phenanthrene, pyrene, fluorene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, pyridopyrazine, triazine, furan, benzofuran, dibenzofuran, imidazole, benzimidazole, thiophene, benzothiophene, dibenzothiophene, 9,9-dimethylfluorene, aromatic amine, carbazole, quinazoline, benzothiazole.

[0053] Preferably, L is selected from the subunits of the following compounds that are chemically bonded, unsubstituted, or substituted by Ra: benzene, biphenyl, naphthalene, phenanthrene, pyrene, fluorene, and imidazole.

[0054] Preferably, the halogen is selected from fluorine, chlorine or bromine; the C1-C4 haloalkyl is selected from C1-C4 fluoroalkyl, C1-C4 chloroalkyl or C1-C4 bromoalkyl.

[0055] Preferably, each of Ra is independently selected from deuterium, fluorine, chlorine, bromine, nitro, cyano, methane, ethane, propane, n-butane, isobutane, phenyl, biphenyl, naphthyl, monofluoromethane, monochloromethane, difluoromethane, dichloromethane, trifluoromethane, chloroform, quinoxalinyl, quinolinyl, pyridinyl, or benzofuranyl.

[0056] Preferably, the compounds provided in this application contain both donor and acceptor units in their molecular structure. The dual introduction of donor units such as sulfur atoms and oxygen atoms, and acceptor units such as carbonyl groups and double-bonded sulfur, can greatly enhance the luminescence intensity. Furthermore, by oxidizing sulfur to sulfones, non-radiative enhancement can also be achieved, resulting in host materials with different luminescence colors.

[0057] In some embodiments of the first aspect of this application, the compound is selected from:

[0058]

[0059]

[0060]

[0061] A second aspect of this application provides a light-emitting layer host material comprising at least one of the compounds provided in the first aspect of this application.

[0062] When the compound of this application is used as the host material of the light-emitting layer, as the host material of the bipolar light-emitting layer, it can balance the characteristics of hole and electron transport, simplify the device structure, facilitate the fabrication of organic electroluminescent devices, and improve the luminous efficiency and lifespan of organic electroluminescent devices.

[0063] A third aspect of this application provides an organic electroluminescent device comprising at least one of the host materials of the light-emitting layer provided in the second aspect of this application. Therefore, the organic electroluminescent device provided by this application has a lower driving voltage, better luminous efficiency, and a longer lifespan.

[0064] In this application, there are no particular restrictions on the type and structure of organic electroluminescent devices. They can be organic electroluminescent devices of different types and structures known in the art, as long as at least one of the light-emitting layer host materials provided in this application can be used.

[0065] In some embodiments of this application, the organic electroluminescent device of this application may be a top-emitting structure, which may include, in order on a substrate, an anode, a hole injection layer, a hole transport layer, an emitting layer, an electron transport layer, an electron injection layer, and a transparent or semi-transparent cathode.

[0066] The organic electroluminescent device of this application can also be a bottom-emitting device, which may include a transparent or semi-transparent anode, a hole injection layer, a hole transport layer, an emitting layer, an electron transport layer, an electron injection layer and a cathode structure sequentially on a substrate.

[0067] The organic electroluminescent device of this application can also be a light-emitting device with a dual-sided light-emitting structure, which may include a transparent or semi-transparent anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and a transparent or semi-transparent cathode structure sequentially on a substrate.

[0068] In addition, the organic electroluminescent device of this application may also 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-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 above layers may be omitted or added. This application does not have a particular limitation on the thickness of the above layers, as long as the purpose of this application can be achieved. For example, the organic electroluminescent device may sequentially include an anode (100nm to 150nm) made of metal, a hole injection layer (5nm to 20nm), a hole transport layer (80nm to 140nm), an electron blocking layer (5nm to 20nm), a light-emitting layer (20nm to 45nm), a hole blocking layer (5nm to 20nm), an electron transport layer (30nm to 40nm), an electron injection layer (5nm to 20nm), a transparent or semi-transparent cathode (100nm to 200nm), and a light extraction layer (50nm to 90nm) on a substrate. For example, Figure 1 A schematic diagram of a typical organic electroluminescent device is shown, in which, from bottom to top, a substrate 1, a reflective anode electrode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode electrode 8 are arranged sequentially.

[0069] Understandable. Figure 1 The structure of a typical organic electroluminescent device is only schematically shown. This application is not limited to this structure. The host material of the light-emitting layer in this application can be used in any type of organic electroluminescent device.

[0070] For convenience, the following references Figure 1The organic electroluminescent device described in this application is not intended to limit the scope of protection of this application. It is understood that all organic electroluminescent devices that can use the light-emitting layer host material of this application are within the scope of protection of this application.

[0071] In this application, the substrate 1 is not particularly limited and can be a conventional substrate used in organic electroluminescent devices in the prior art, such as glass, polymer materials, and glass and polymer materials with thin-film transistor (TFT) components.

[0072] In this application, the material of the reflective anode electrode 2 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 electrode 2 can be a multilayer structure formed from the above materials. This application does not particularly limit the number of layers in its multilayer structure. It can be selected according to actual needs, as long as the purpose of this application can be achieved. For example, one layer, two layers, three layers, or more layers.

[0073] In this application, the material of the hole injection layer 3 is not particularly limited, and it can be made of hole injection layer materials known in the art or hole transport materials (HTMs) known in the art. For example, at least one of the known hole transport materials (HTMs) can be selected as the hole injection material.

[0074] In this application, the hole injection layer 3 may further include a p-type dopant. This 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 may be selected from, but is not limited to, at least one of the following p-1 to p-3 compounds:

[0075]

[0076] In this application, the amount of p-type dopant used is not particularly limited and can be any amount known to those skilled in the art.

[0077] In this application, the material of the hole transport layer 4 is not particularly limited and can be made of hole transport materials (HTM) known in the art. The number of layers of the hole transport layer 4 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.

[0078] For example, HTM for hole injection layer materials and HTM for hole transport layer materials can be selected from, but are not limited to, at least one of the following HT-1 to HT-31 compounds:

[0079]

[0080]

[0081] In this application, the light-emitting layer 5 may include a blue light-emitting layer, a green light-emitting layer, or a red light-emitting layer, and the material of the light-emitting layer 5 may include a light-emitting layer host material and a light-emitting layer guest material.

[0082] In this application, the light-emitting layer host material includes at least one of the light-emitting layer host materials of this application.

[0083] In this application, there are no particular restrictions on the amount of the main material of the light-emitting layer, and the amount can be known to those skilled in the art.

[0084] In this application, the guest material of the luminescent layer is not particularly limited, and at least one of the luminescent layer guest materials known in the art can be used. For example, the luminescent layer guest material can be selected from, but is not limited to, at least one of the following BD-1 to BD-9 compounds:

[0085]

[0086] In this application, there is no particular limitation on the amount of the luminescent layer guest material, and it can be any amount known to those skilled in the art.

[0087] In this application, the material of the electron transport layer 6 is not particularly limited and can be made of electron transport materials known in the art. The number of layers in the electron transport layer 6 is not particularly limited and can be adjusted according to actual needs, as long as the purpose of this application is met; for example, one, two, three, four, or more layers.

[0088] For example, the electron transport material may be selected from, but is not limited to, at least one of the following ET-1 to ET-57 compounds:

[0089]

[0090]

[0091]

[0092] In this application, the electron transport layer 6 may further include an n-type dopant. This application does not impose any particular limitation 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:

[0093]

[0094] In this application, there is no particular limitation on the amount of the n-type dopant, and it can be any amount known to those skilled in the art.

[0095] In this application, the material of the electron injection layer 7 is not particularly limited, and electron injection materials known in the art can be used. For example, it can include, but is not limited to, at least one of the following materials in the prior art: lithium 8-hydroxyquinoline (LiQ), LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, etc.

[0096] In this application, the material of the cathode electrode 8 is not particularly limited and can be selected from, but is not limited to, magnesium-silver mixtures, LiF / Al, ITO, Al and other metals, metal mixtures, oxides and the like.

[0097] There are no particular limitations on the method for preparing the organic electroluminescent device of this application; any method known in the art can be used. For example, this application can be prepared using the following method:

[0098] (1) Clean the reflective anode electrode 2 on the substrate 1 of the top-emitting OLED device. In the cleaning machine, the electrode is cleaned by chemical washing, water washing, brushing, high-pressure water washing, air knife and other steps, and then heated.

[0099] (2) Hole injection material is vacuum-deposited on the reflective anode electrode 2 as a hole injection layer 3;

[0100] (3) Hole transport material is vacuum-deposited on hole injection layer 3 as hole transport layer 4;

[0101] (4) A light-emitting layer 5 is vacuum-deposited on the hole transport layer 4, wherein the light-emitting layer 5 contains a light-emitting layer host material and a light-emitting layer guest material;

[0102] (5) Electron transport material is vacuum-deposited on the light-emitting layer 5 as electron transport layer 6;

[0103] (6) Vacuum evaporation of electron injection material on electron transport layer 6 to serve as electron injection layer 7;

[0104] (7) Vacuum evaporation of cathode material on electron injection layer 7 as cathode electrode 8.

[0105] The above describes only a typical structure and fabrication method of an organic electroluminescent device. It should be understood that this application is not limited to this structure. The host material of the light-emitting layer in this application can be used in organic electroluminescent devices of any structure, and the organic electroluminescent device can be fabricated using any fabrication method known in the art.

[0106] A fourth aspect of this application provides a display device that includes the organic electroluminescent device provided in the third aspect of this application. The display device includes, but is not limited to, a monitor, a television, a tablet computer, a mobile communication terminal, etc.

[0107] 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. As used herein, room temperature / normal temperature refers to 25±5℃.

[0108] Synthesis example

[0109] Synthesis Example 1: Synthesis of compound H3:

[0110]

[0111] (a) Under a nitrogen atmosphere, 9,9-dimethyl-2-bromofluorene (10 mmol, 2.73 g), phenoxazine (11 mmol, 2.02 g), palladium acetate (Pd(OAc)2, 0.25 mmol, 0.056 g), tri-tert-butylphosphine tetrafluoroborate ([(t-Bu)3PH]BF4, 0.75 mmol, 0.218 g), and sodium tert-butoxide (NaOt-Bu, 20 mmol, 1.92 g) were added to a 100 mL round-bottom flask, and the mixture was reacted under reflux (120 °C) for 24 h with toluene (50 mL) as the solvent. After the reaction was completed, water was added to quench the reaction, and the aqueous phase was extracted with toluene. The resulting organic phase was dried with anhydrous sodium sulfate (Na2SO4), and then evaporated under reduced pressure. The solid obtained was purified by column chromatography (n-hexane: dichloromethane = 10:1) to give a light yellow solid, namely intermediate 1 (2.4 g, yield 80%).

[0112] 1 H NMR (500MHz, CDCl3) δ1.73 (s, 6H), 6.89-6.95 (m, 4H), 7.02-7.08 (m, 2H), 7.14 (dt, J = 3.67, 7.18Hz, 2H), 7.44 (td, J = 1.3 2,7.50Hz,1H),7.53(td,J=1.37,8.38Hz,2H),7.63(dd,J=1.14,7.39Hz,1H),7.68(d,J=1.21Hz,1H),7.80-7.86(m,2H).

[0113] (b) In a 100 mL round-bottom flask, intermediate 1 (10 mmol, 3.75 g) was dissolved in tetrahydrofuran (THF, 50 mL). Under a nitrogen atmosphere at 0 °C, 10 mL of THF solution containing N-bromosuccinimide (NBS, 11 mmol, 1.96 g) was added in portions. The reaction was monitored by thin-layer chromatography. After the reaction was complete, the mixture was quenched with water, extracted with ethyl acetate, and concentrated under reduced pressure. Finally, the mixture was purified by column chromatography (n-hexane:ethyl acetate = 10:1) to obtain a light green solid, intermediate 2 (1.14 g, 25%).

[0114] 1 H NMR(500MHz, CDCl3)δ1.73(s,6H),6.92(dd,J=3.81,5.81Hz,2H),7.00-7.10(m,3H),7.14(dd,J=3.93,5.66Hz,1H ),7.30(d,J=1.88Hz,1H),7.44(td,J=1.54,7.41Hz,1H),7.48-7.58(m,2H),7.60-7.69(m,2H),7.79-7.87(m,2H).

[0115] (c) Under a nitrogen atmosphere, intermediate 2 (5 mmol, 2.27 g), 4-benzoylphenylboronic acid (6 mmol, 1.36 g), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 0.05 mmol, 58 mg), and potassium carbonate (K2CO3, 10 mmol, 1.38 g) were added to a 100 mL round-bottom flask, along with 50 mL of toluene, 5 mL of ethanol, and 5 mL of water. The mixture was refluxed at 85 °C for 6 h. After the reaction was complete, the aqueous phase was extracted with toluene, and the resulting organic phase was dried over anhydrous sodium sulfate. The organic phase was then purified by rotary evaporation under reduced pressure and column chromatography (n-hexane:dichloromethane = 5:1) to give a white solid (2.36 g, 85% yield).

[0116] 1 H NMR (500MHz, CDCl3) δ1.74 (s, 6H), 6.89-6.96 (m, 2H), 7.04-7.11 (m, 1H), 7.13-7.23 (m, 2H), 7.32 (d, J = 7.52Hz, 1H),7.41-7.59(m,7H),7.63(dd,J=1.67,7.43Hz,1H),7.69-7.72m,5H),7.81-7.88(m,2H),7.90-7.96(m,2H).

[0117] M / Z: Experimental value, 556.0136; Theoretical value, 555.2198.

[0118] Synthesis Example 2: Synthesis of compound H4:

[0119]

[0120] (a) Under a nitrogen atmosphere, p-bromobenzonitrile (10 mmol, 1.82 g), phenothiazine (11 mmol, 2.19 g), Pd(OAc)₂ (0.25 mmol, 0.056 g), tri-tert-butylphosphine tetrafluoroborate (0.75 mmol, 0.218 g), and sodium tert-butoxide (20 mmol, 1.92 g) were added to a 250 mL round-bottom flask. The reaction was carried out under reflux (120 °C) for 24 h with toluene (100 mL) as solvent. After the reaction was completed, the mixture was quenched with water, and the aqueous phase was extracted with toluene. The resulting organic phase was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The solid obtained was purified by column chromatography (n-hexane: dichloromethane = 10:1) to give a pale yellow solid, namely intermediate 1 (2.4 g, yield 80%).

[0121] 1 H NMR (500MHz, CDCl3) δ6.87 (dd, J=1.99, 7.46Hz, 2H), 7.02 (td, J=2.05, 7.51Hz, 2H), 7.12 (td, J = 1.95, 7.42Hz, 2H), 7.50-7.61 (m, 4H), 7.74 (d, J = 7.55Hz, 2H).

[0122] (b) Under a nitrogen atmosphere, intermediate 1 (2 mmol, 0.6 g) and anhydrous aluminum chloride (AlCl3, 2.4 mmol, 0.32 g) were stirred in anhydrous dichloromethane (CH2Cl2, 30 mL) in a 100 mL round-bottom flask. Benzoyl chloride (2.4 mmol, 0.34 g) was added to the reaction system under ice-water bath conditions. The mixture was heated to reflux at 40 °C for 6 hours. After the reaction was completed, the reaction solution was poured into 10 mL of 10% (v / v) glacial hydrochloric acid-water solution (i.e., hydrochloric acid-water solution at 0 °C). The mixture was extracted three times with dichloromethane, evaporated under reduced pressure, and finally purified by column chromatography (dichloromethane: n-hexane = 1:2) to obtain a yellow-green solid, namely intermediate 2 (0.484 g, yield 60%).

[0123] 1 H NMR (500MHz, CDCl3) δ6.89 (dd, J=7.5, 2.0Hz, 1H), 6.97-7.06 (m, 2H), 7.13 (td, J=7.5, 2.0H z, 1H), 7.45 (t, J = 7.4Hz, 2H), 7.50-7.60 (m, 5H), 7.68-7.75 (m, 4H), 7.89 (d, J = 1.9Hz, 1H).

[0124] (c) Intermediate product 2 (2 mmol, 0.8 g) was placed in a 50 mL single-necked flask, and dichloromethane (20 mL) and glacial acetic acid (CH3COOH, 10 mL) were added. The mixture was stirred for 10 min, and then 30% hydrogen peroxide solution (H2O2, 2 mL) was slowly added. The mixture was heated to reflux at 60 °C for 24 h. After the reaction was completed, the pH was adjusted to neutral, and the mixture was extracted with dichloromethane. Then, column chromatography was performed to purify the product using a mixed solvent of petroleum ether and dichloromethane (petroleum ether: dichloromethane = 1:1) as the eluent. Recrystallization was then performed to obtain a white solid powder (0.7 g, yield 80%).

[0125] 1 H NMR (500MHz, CDCl3) δ7.25 (td, J=2.47, 7.33Hz, 1H), 7.34-7.56 (m, 6H), 7.58 -7.64(m,2H),7.67-7.77(m,4H),8.06-8.10(m,2H),8.61(d,J=1.84Hz,1H).

[0126] M / Z: Experimental value, 437.2585; Theoretical value, 436.0882.

[0127] Synthesis Example 3: Synthesis of Compound H8:

[0128]

[0129] (a) Under a nitrogen atmosphere, 9-bromophenanthrene (6 mmol, 1.543 g), phenothiazine (7.2 mmol, 1.435 g), Pd(OAc)₂ (0.15 mmol, 0.034 g), tri-tert-butylphosphine tetrafluoroborate (0.45 mmol, 0.131 g), and sodium tert-butoxide (12 mmol, 1.153 g) were added to a 250 mL round-bottom flask. The reaction was carried out under reflux (120 °C) for 24 h with toluene (100 mL) as solvent. After the reaction was completed, the mixture was quenched with water, and the aqueous phase was extracted with toluene. The resulting organic phase was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The solid obtained was purified by column chromatography (petroleum ether) to give a pale yellow solid, namely intermediate 1 (1.9 g, yield 84%).

[0130] 1 H NMR (500MHz, CDCl3) δ6.91-7.14(m,6H),7.5-7.72(m,6H),7.87(s,1H),7.99(d,J=7.3Hz,1H),8.20(dd,J=7.5,1.2Hz,1H),8.80-8.94(m,2H).

[0131] (b) Under a nitrogen atmosphere, intermediate 1 (4 mmol, 1.49 g) and anhydrous aluminum chloride (4.8 mmol, 0.635 g) were added to a 100 mL round-bottom flask, followed by stirring with anhydrous dichloromethane (40 mL). After stirring at room temperature for 15 minutes, benzoyl chloride (4.8 mmol, 0.669 g) was added to the reaction system under ice-water bath conditions. The mixture was heated to reflux at 40 °C for 6 hours. After the reaction was completed, the reaction solution was poured into 13 mL of 10% (v / v) glacial hydrochloric acid-water solution (i.e., hydrochloric acid-water solution at 0 °C), extracted three times with dichloromethane, rotary evaporated under reduced pressure, and finally purified by column chromatography (n-hexane:dichloromethane = 2:1) to obtain a yellow solid, namely intermediate 2 (1.2 g, yield 63%).

[0132] 1 H NMR (500MHz, CDCl3) δ6.97-7.06(m,2H),7.06-7.14(m,2H),7.41-7.74(m,11H),7.91(dd,J=1.75,17.61Hz,2H),7.99( dt,J=1.63,7.33Hz,1H),8.21(dd,J=1.55,7.41Hz,1H),8.84(dd,J=1.56,7.36Hz,1H),8.91(dd,J=1.46,7.66Hz,1H).

[0133] (c) Intermediate product 2 (0.96 g, 2 mmol) was placed in a 50 mL single-necked flask, and dichloromethane (20 mL) and glacial acetic acid (10 mL) were added. The mixture was stirred for 10 min, and then 30% hydrogen peroxide solution (2 mL) was slowly added. The mixture was heated to reflux at 60 °C for 24 h. After the reaction was completed, the pH was adjusted to neutral, and the mixture was extracted with dichloromethane. Then, column chromatography was performed to purify the product using a mixed solvent of petroleum ether and dichloromethane (petroleum ether: dichloromethane = 1:1) as the eluent. Recrystallization was then performed to obtain a white solid powder (0.84 g, yield 82%).

[0134] 1H NMR(500MHz, CDCl3)δ7.25(td,J=1.99,7.31Hz,1H),7.34(td,J=2.01,7.51H z,1H),7.39-7.75(m,11H),7.96(d,J=1.35Hz,1H),8.02(td,J=1.85,7.76Hz ,2H),8.12(dd,J=2.12,7.45Hz,1H),8.18(dd,J=1.54,7.37Hz,1H),8.63(d, J=2.05Hz, 1H), 8.84 (dd, J=1.55, 7.33Hz, 1H), 8.92 (dd, J=1.53, 7.43Hz, 1H).

[0135] M / Z: Experimental value, 512.0375; Theoretical value, 511.1242.

[0136] Synthesis Example 4: Synthesis of compound H10:

[0137]

[0138] (a) Under a nitrogen atmosphere, 4-bromotrifluorotoluene (10 mmol, 2.24 g), phenothiazine (11 mmol, 2.2 g), Pd(OAc)₂ (0.25 mmol, 0.056 g), tri-tert-butylphosphine tetrafluoroborate (0.75 mmol, 0.218 g), and sodium tert-butoxide (20 mmol, 1.92 g) were added to a 250 mL round-bottom flask. The reaction was carried out under reflux (120 °C) for 24 h with toluene (100 mL) as solvent. After the reaction was completed, the mixture was quenched with water, and the aqueous phase was extracted with dichloromethane. The resulting organic phase was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The solid obtained was purified by column chromatography (n-hexane:dichloromethane = 10:1) to give a pale yellow solid, namely intermediate 1 (2.6 g, yield 76%).

[0139] 1 H NMR(500MHz, CDCl3) δ6.88(dd,J=2.02,7.36Hz,2H),7.01(td,J=2.01,7.51Hz,2H),7.11(td,J =2.12,7.53Hz,2H),7.45-7.50(m,2H),7.52(dd,J=2.04,7.49Hz,2H),7.60(d,J=7.29Hz,2H).

[0140] (b) Under a nitrogen atmosphere, intermediate 1 (2 mmol, 0.69 g) and anhydrous aluminum chloride (2.4 mmol, 0.32 g) were stirred in anhydrous dichloromethane (30 mL) in a 100 mL round-bottom flask. Benzoyl chloride (2.4 mmol, 0.34 g) was added to the reaction system under ice-water bath conditions. The mixture was heated to reflux at 40 °C for 6 hours. After the reaction was completed, the reaction solution was poured into 10 mL of 10% (v / v) glacial hydrochloric acid-water solution (i.e., hydrochloric acid-water solution at 0 °C). The mixture was extracted three times with dichloromethane, evaporated under reduced pressure, and finally purified by column chromatography (dichloromethane: n-hexane = 4:1) to obtain a pale yellow solid, namely intermediate 2 (0.54 g, yield 60%).

[0141] 1 H NMR (500MHz, CDCl3) δ6.89 (dd, J=2.07, 7.39Hz, 1H), 6.97-7.06 (m, 2H), 7.12 (td, J=2.00, 7.40 Hz,1H),7.41-7.57(m,7H),7.61(d,J=7.23Hz,2H),7.67-7.74(m,2H),7.92(d,J=1.95Hz,1H).

[0142] (c) Intermediate product 2 (0.54 g, 2 mmol) was placed in a 50 mL single-necked flask, and dichloromethane (20 mL) and glacial acetic acid (10 mL) were added. The mixture was stirred for 10 min, and then 30% hydrogen peroxide solution (2 mL) was slowly added. The mixture was heated to reflux at 60 °C for 24 h. After the reaction was completed, the pH was adjusted to neutral, and the mixture was extracted with dichloromethane. Then, column chromatography was performed to purify the product using a mixed solvent of petroleum ether and dichloromethane (petroleum ether: dichloromethane = 1:1) as the eluent. Recrystallization was then performed to obtain a white solid powder (0.82 g, yield 86%).

[0143] 1 H NMR (500MHz, CDCl3) δ7.24 (td, J=7.2, 2.2Hz, 1H), 7.32-7.58 (m, 8H), 7.63 (d, J=7.6Hz, 2H), 7.6 7-7.75(m,2H),7.98(dd,J=7.5,2.0Hz,1H),8.11(dd,J=7.4,2.0Hz,1H),8.60(d,J=2.0Hz,1H).

[0144] M / Z: Experimental value, 480.3617; Theoretical value, 479.0803.

[0145] Synthesis Example 5: Synthesis of compound H15:

[0146]

[0147] (a) Under a nitrogen atmosphere, 5-bromopyrimidine (10 mmol, 1.59 g), phenothiazine (11 mmol, 2.19 g), Pd(OAc)₂ (0.25 mmol, 0.056 g), tri-tert-butylphosphine tetrafluoroborate (0.75 mmol, 0.218 g), and sodium tert-butoxide (20 mmol, 1.92 g) were added to a 250 mL round-bottom flask. The reaction was carried out under reflux (120 °C) for 24 h with toluene (100 mL) as solvent. After the reaction was completed, the mixture was quenched with water, and the aqueous phase was extracted with toluene. The resulting organic phase was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The solid obtained was purified by column chromatography (n-hexane:dichloromethane = 10:1) to give a pale yellow solid, namely intermediate 1 (2.24 g, yield 81%).

[0148] 1 H NMR (500MHz, CDCl3) δ6.91 (dd, J=7.4, 2.0Hz, 2H), 7.02 (td, J=7.4, 2.0Hz, 2H), 7. 14(td,J=7.4,2.0Hz,2H),7.53(dd,J=7.5,2.1Hz,2H),8.81(s,2H),9.07(s,1H).

[0149] (b) Under a nitrogen atmosphere, intermediate 1 (2 mmol, 0.55 g) and anhydrous aluminum chloride (2.4 mmol, 0.32 g) were stirred in anhydrous dichloromethane (30 mL) in a 100 mL round-bottom flask. Benzoyl chloride (2.4 mmol, 0.34 g) was added to the reaction system under ice-water bath conditions. The mixture was heated to reflux at 40 °C for 6 hours. After the reaction was completed, the reaction solution was poured into 10 mL of 10% (v / v) glacial hydrochloric acid-water solution (i.e., hydrochloric acid-water solution at 0 °C). The mixture was extracted three times with dichloromethane, evaporated under reduced pressure, and finally purified by column chromatography (dichloromethane: n-hexane = 1:1) to obtain a pale yellow solid, namely intermediate 2 (0.62 g, yield 81%).

[0150] 1 H NMR (500MHz, CDCl3) δ6.93 (dd, J=7.4, 2.1Hz, 1H), 6.99-7.08 (m, 2H), 7.15 (td, J=7.5, 2.0Hz ,1H),7.40-7.57(m,5H),7.67-7.73(m,2H),7.84(d,J=2.0Hz,1H),8.83(s,2H),9.08(s,1H).

[0151] (c) Intermediate product 2 (0.76 g, 2 mmol) was placed in a 50 mL single-necked flask, and dichloromethane (20 mL) and glacial acetic acid (10 mL) were added. The mixture was stirred for 10 min, and then 30% hydrogen peroxide solution (2 mL) was slowly added. The mixture was heated to reflux at 60 °C for 24 h. After the reaction was completed, the pH was adjusted to neutral, and the mixture was extracted with dichloromethane. Then, column chromatography was performed to purify the product using a mixed solvent of petroleum ether and dichloromethane (petroleum ether: dichloromethane = 1:1) as the eluent. Recrystallization was then performed to obtain a white solid powder (0.74 g, yield 90%).

[0152] 1 H NMR (500MHz, CDCl3) δ7.25 (td, J=7.5, 2.1Hz, 1H), 7.35-7.58 (m, 6H), 7.66-7. 74(m,2H),8.03-8.10(m,2H),8.56(d,J=2.1Hz,1H),8.87(s,2H),9.12(s,1H).

[0153] M / Z: Experimental value, 414.2215; Theoretical value, 413.0834.

[0154] Synthesis Example 6: Synthesis of compound H25:

[0155]

[0156] (a) Under a nitrogen atmosphere, 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (10 mmol, 3.88 g), phenothiazine (11 mmol, 2.19 g), Pd(OAc)₂ (0.25 mmol, 0.056 g), tri-tert-butylphosphine tetrafluoroborate (0.75 mmol, 0.218 g), and sodium tert-butoxide (20 mmol, 1.92 g) were added to a 250 mL round-bottom flask. The reaction was carried out under reflux (120 °C) for 24 h with toluene (100 mL) as solvent. After the reaction was completed, the mixture was quenched with water, and the aqueous phase was extracted with toluene. The resulting organic phase was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The solid obtained was purified by column chromatography (n-hexane:dichloromethane = 10:1) to give a pale yellow solid, namely intermediate 1 (4 g, yield 79%).

[0157] 1 H NMR (500MHz, CDCl3) δ6.94-7.07(m,4H),7.13(td,J=7.5,2.0Hz,2H),7.45-7.59(m,8H),7.59-7.66(m,2H),8.18-8.27(m,2H),8.34-8.37(m,4H).

[0158] (b) Under a nitrogen atmosphere, intermediate 1 (2 mmol, 1 g) and anhydrous aluminum chloride (2.4 mmol, 0.32 g) were stirred in anhydrous dichloromethane (30 mL) in a 100 mL round-bottom flask. Benzoyl chloride (2.4 mmol, 0.34 g) was added to the reaction system under ice-water bath conditions. The mixture was heated to reflux at 40 °C for 6 hours. After the reaction was completed, the reaction solution was poured into 10 mL of 10% (v / v) glacial hydrochloric acid-water solution (i.e., hydrochloric acid-water solution at 0 °C). The mixture was extracted three times with dichloromethane, evaporated under reduced pressure, and finally purified by column chromatography (dichloromethane: n-hexane = 1:1) to obtain a yellow solid, namely intermediate 2 (1 g, yield 82%).

[0159] 1 H NMR (500MHz, CDCl3) δ6.94-7.18(m,4H),7.40-7.59(m,11H),7.65(d,J=7.48Hz,2H),7.70( dd,J=1.83,7.50Hz,2H),7.89(d,J=2.01Hz,1H),8.24(d,J=7.55Hz,2H),8.30-8.39(m,4H).

[0160] (c) Intermediate product 2 (0.6 g, 1 mmol) was placed in a 50 mL single-necked flask, and dichloromethane (20 mL) and glacial acetic acid (10 mL) were added. The mixture was stirred for 10 min, and then 30% hydrogen peroxide solution (2 mL) was slowly added. The mixture was heated to reflux at 40 °C for 24 h. After the reaction was completed, the pH was adjusted to neutral, and the mixture was extracted with dichloromethane. Then, column chromatography was performed to purify the product using a mixed solvent of petroleum ether and dichloromethane (petroleum ether: dichloromethane = 1:1) as the eluent. Recrystallization was then performed to obtain a white solid powder (0.55 g, yield 86%).

[0161] 1 H NMR (500MHz, CDCl3) δ7.25(td,J=7.5,2.0Hz,1H),7.38(td,J=7.5,2.0Hz,1H),7.41-7.56(m,10H),7.59(d,J=7.5Hz,1H),7.69(td,J=6. 3,5.4,1.8Hz,4H),7.95(dd,J=7.5,2.0Hz,1H),8.12(dd,J=7.5,2.1Hz,1H),8.23-8.31(m,2H),8.31-8.39(m,4H),8.57(d,J=1.9Hz,1H).

[0162] M / Z: Experimental value, 643.0315; Theoretical value, 642.1726.

[0163] Synthesis Example 7: Synthesis of compound H36:

[0164]

[0165] (a) Under a nitrogen atmosphere, bromobenzene (10 mmol, 1.57 g), phenothiazine (11 mmol, 2.19 g), Pd(OAc)₂ (0.25 mmol, 0.056 g), tri-tert-butylphosphine tetrafluoroborate (0.75 mmol, 0.218 g), and sodium tert-butoxide (20 mmol, 1.92 g) were added to a 250 mL round-bottom flask. The reaction was carried out under reflux (120 °C) for 24 h with toluene (100 mL) as solvent. After the reaction was completed, the mixture was quenched with water, and the aqueous phase was extracted with toluene. The resulting organic phase was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The solid obtained was purified by column chromatography (n-hexane:dichloromethane = 10:1) to give a pale yellow solid, namely intermediate 1 (2.2 g, yield 80%).

[0166] 1 H NMR (500MHz, CDCl3) δ6.92 (dd, J=2.04, 7.42Hz, 2H), 7.00 (tt, J=2.24, 7.45Hz, 3H), 7.11 (td, J=1.95 ,7.51Hz,2H),7.24(t,J=7.50Hz,2H),7.38(dd,J=1.90,7.50Hz,2H),7.52(dd,J=1.94,7.41Hz,2H).

[0167] (b) Under a nitrogen atmosphere, intermediate 1 (5 mmol, 1.38 g) and anhydrous aluminum chloride (6 mmol, 0.8 g) were stirred in anhydrous dichloromethane (30 mL) in a 100 mL round-bottom flask. Pyridine-2-formyl chloride hydrochloride (6 mmol, 1.07 g) was added to the reaction system under ice-water bath conditions. The mixture was heated to reflux at 40 °C for 6 hours. After the reaction was completed, the reaction solution was poured into 16 mL of 10% (v / v) glacial hydrochloric acid-water solution (i.e., hydrochloric acid-water solution at 0 °C). The mixture was extracted three times with dichloromethane, evaporated under reduced pressure, and finally purified by column chromatography (dichloromethane: n-hexane = 1:1) to obtain a bright yellow solid, namely intermediate 2 (1.05 g, yield 55%).

[0168] 1H NMR (500MHz, CDCl3) δ6.94 (dd, J=2.07, 7.47Hz, 1H), 6.97-7.06 (m, 3H), 7.12 (td,J=2.02,7.41Hz,1H),7.24(t,J=7.53Hz,2H),7.36-7.43(m,2H),7.54(dd ,J=2.05,7.45Hz,1H),7.65(dd,J=2.00,7.51Hz,1H),7.77-7.79(m,1H),7.9 5(td,J=1.27,8.06Hz,1H),8.07-8.17(m,2H),8.87(dd,J=1.27,5.03Hz,1H).

[0169] (c) Intermediate product 2 (1.14 g, 3 mmol) was placed in a 50 mL single-necked flask, and dichloromethane (20 mL) and glacial acetic acid (10 mL) were added. The mixture was stirred for 10 min, and then 30% hydrogen peroxide solution (2 mL) was slowly added. The mixture was heated to reflux at 60 °C for 24 h. After the reaction was completed, the pH was adjusted to neutral, and the mixture was extracted with dichloromethane. Then, column chromatography was performed to purify the product using a mixed solvent of petroleum ether and dichloromethane (petroleum ether: dichloromethane = 1:1) as the eluent. Recrystallization was then performed to obtain a white solid powder (1.05 g, yield 85%).

[0170] 1 H NMR(500MHz, CDCl3)δ7.00(tt,J=1.99,7.33Hz,1H),7.24(td,J=2.21,7.55Hz,3 H),7.36(td,J=2.00,7.50Hz,1H),7.42-7.5(m,3H),7.52(d,J=7.51Hz,1H),7.77 -7.80(m,1H),7.94(td,J=1.28,7.97Hz,1H),8.09-8.14(m,2H),8.17(dd,J =2.01, 7.51Hz, 1H), 8.80 (d, J = 2.07Hz, 1H), 8.89 (dd, J = 1.27, 5.04Hz, 1H).

[0171] M / Z: Experimental value, 413.3167; Theoretical value, 412.0882.

[0172] Synthesis Example 8: Synthesis of compound H37:

[0173]

[0174] (a) Under a nitrogen atmosphere, bromobenzene (10 mmol, 1.57 g), phenothiazine (11 mmol, 2.19 g), Pd(OAc)₂ (0.25 mmol, 0.056 g), tri-tert-butylphosphine tetrafluoroborate (0.75 mmol, 0.218 g), and sodium tert-butoxide (20 mmol, 1.92 g) were added to a 250 mL round-bottom flask. The reaction was carried out under reflux (120 °C) for 24 h with toluene (100 mL) as solvent. After the reaction was completed, the mixture was quenched with water, and the aqueous phase was extracted with toluene. The resulting organic phase was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The solid obtained was purified by column chromatography (n-hexane:dichloromethane = 10:1) to give a pale yellow solid, namely intermediate 1 (2.2 g, yield 80%).

[0175] 1 H NMR (500MHz, CDCl3) δ6.92 (dd, J=2.04, 7.42Hz, 2H), 7.00 (tt, J=2.24, 7.45Hz, 3H), 7.11 (td, J=1.95 ,7.51Hz,2H),7.24(t,J=7.50Hz,2H),7.38(dd,J=1.90,7.50Hz,2H),7.52(dd,J=1.94,7.41Hz,2H).

[0176] (b) Under a nitrogen atmosphere, intermediate 1 (2.75 g, 10 mmol) was dissolved in a 60 mL mixture of acetic acid and chloroform (Vacetic acid:Vchloroform = 1:1) in a 100 mL round-bottom flask. N-bromosuccinimide (1.96 g, 11 mmol) was added in portions, and the reaction was carried out at room temperature for 6 h. The pH was then adjusted to neutral, and the mixture was extracted with ethyl acetate and dried over anhydrous Na2SO4 to obtain the crude product. The crude product was recrystallized from dichloromethane and methanol to give a reddish-brown solid, which was intermediate 2 (0.7 g, 20% yield).

[0177] 1 H NMR(500MHz, CDCl3)δ6.81(d,J=7.49Hz,1H),6.92(dd,J=2.01,7.33Hz,1H),6.98-7.02(m,2H),7.11(td,J=2.10,7.43Hz,1H) ,7.17(dd,J=2.01,7.51Hz,1H),7.20-7.28(m,2H),7.34-7.41(m,2H),7.52(dd,J=2.03,7.43Hz,1H),7.58(d,J=2.06Hz,1H).

[0178] (c) Under a nitrogen atmosphere, intermediate 2 (3 mmol, 1.06 g), 3-(1H-imidazolium-2-carbonyl)pyridine (3 mmol, 0.52 g), palladium acetate (0.075 mmol, 17 mg), tri-tert-butylphosphine tetrafluoroborate (0.225 mmol, 65 mg), and sodium tert-butoxide (6 mmol, 0.58 g) were added to a 100 mL round-bottom flask. The reaction was carried out under reflux (120 °C) for 24 h with toluene (50 mL) as solvent. After the reaction was completed, the mixture was quenched with water, and the aqueous phase was extracted with toluene. The resulting organic phase was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The solid obtained was purified by column chromatography (n-hexane:dichloromethane = 5:1) to give a pale yellow solid, namely intermediate 3 (0.94 g, yield 70%).

[0179] 1 H NMR(500MHz, CDCl3)δ6.98-7.02(m,2H),7.11(td,J=2.01,7.52Hz,1H),7.15-7.21(m ,2H),7.24(t,J=7.52Hz,2H),7.37-7.44(m,2H),7.48-7.53(m,2H),7.65(dd,J=1.92, 7.42Hz,1H),7.72(d,J=7.48Hz,1H),7.81(d,J=2.06Hz,1H),8.09(d,J=7.49Hz,1H), 8.27(dt,J=1.40,8.00Hz,1H), 8.75(dd,J=1.33,5.02Hz,1H), 9.21(d,J=1.21Hz,1H).

[0180] (d) Intermediate product 3 (2 mmol, 0.89 g) was placed in a 50 mL single-necked flask, and dichloromethane (10 mL) and glacial acetic acid (5 mL) were added. The mixture was stirred for 10 min, and then 30% hydrogen peroxide solution (2 mL) was slowly added. The mixture was heated to reflux at 60 °C for 24 h. After the reaction was completed, the pH was adjusted to neutral, and the mixture was extracted with dichloromethane. Then, column chromatography was performed to purify the product using a mixed solvent of petroleum ether and dichloromethane (petroleum ether: dichloromethane = 1:1) as the eluent. Recrystallization was then performed to obtain a white solid powder (0.78 g, yield 82%).

[0181] 1H NMR (500MHz, CDCl3) δ7.00(tt,J=2.00,7.36Hz,1H),7.23(td,J=5.78,7.53Hz,3H),7.35(td,J=2.01,7.50Hz,1H),7.40-7. 52(m,5H),7.66-7.75(m,2H),8.05-8.11(m,2H),8.22-8.30(m,2H),8.75(dd,J=1.28,5.03Hz,1H),9.21(d,J=1.21Hz,1H).

[0182] M / Z: Experimental value, 479.2139; Theoretical value, 478.1100.

[0183] Synthesis Example 9: Synthesis of compound H38:

[0184]

[0185] (a) Under a nitrogen atmosphere, 10H-spiro[acridin-9,9'-oxazanthene] (10 mmol, 3.47 g), bromobenzene (11 mmol, 1.73 g), Pd(OAc)₂ (0.25 mmol, 0.0561 g), tri-tert-butylphosphine tetrafluoroborate (0.75 mmol, 0.2176 g), and sodium tert-butoxide (20 mmol, 1.92 g) were added to a 250 mL round-bottom flask. The reaction was carried out under reflux (120 °C) for 24 h with toluene (100 mL) as solvent. After the reaction was completed, the mixture was quenched with water, and the aqueous phase was extracted with toluene. The resulting organic phase was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The solid obtained was purified by column chromatography (n-hexane:dichloromethane = 10:1) to give a pale yellow solid, namely intermediate 1 (3 g, yield 71%).

[0186] 1 H NMR (500MHz, CDCl3) δ6.89 (td, J = 2.05, 7.46Hz, 2H), 6.95-7.05 (m, 5H), 7.07-7. 10(m,4H),7.20-7.30(m,4H),7.37(dd,J=1.90,7.46Hz,2H),7.40-7.48(m,4H).

[0187] (b) Under a nitrogen atmosphere, intermediate 1 (3 mmol, 1.27 g) and anhydrous aluminum chloride (3.6 mmol, 0.48 g) were stirred in anhydrous dichloromethane (30 mL) in a 100 mL round-bottom flask. Benzoyl chloride (3.6 mmol, 0.51 g) was added to the reaction system under ice-water bath conditions. The mixture was heated to reflux at 40 °C for 6 hours. After the reaction was completed, the reaction solution was poured into 10 mL of 10% (v / v) glacial hydrochloric acid-water solution (i.e., hydrochloric acid-water solution at 0 °C). The mixture was extracted three times with dichloromethane, evaporated under reduced pressure, and finally purified by column chromatography (dichloromethane: n-hexane = 1:1) to give a bright yellow solid (0.87 g, yield 55%).

[0188] 1 H NMR(500MHz, CDCl3)δ6.91(td,J=2.05,7.47Hz,1H),6.95-7.07(m,5H),7.07-7.15(m,3H),7.19 -7.29(m,3H),7.30-7.41(m,2H),7.41-7.57(m,7H),7.67-7.71(m,3H),7.79(d,J=2.04Hz,1H).

[0189] M / Z: Experimental value, 528.0115; Theoretical value, 527.1885.

[0190] Synthesis Example 10: Synthesis of Compound H44

[0191]

[0192] Under a nitrogen atmosphere, 3-bromo-9,9-diphenyl-9H-oxanthracene (5 mmol, 2.07 g), 4-benzoylphenylboronic acid (6 mmol, 1.36 g), tetrakis(triphenylphosphine)palladium (0.05 mmol, 58 mg), and potassium carbonate (10 mmol, 1.38 g) were added to a 100 mL round-bottom flask, along with 50 mL of toluene, 5 mL of ethanol, and 5 mL of water. The mixture was refluxed at 85 °C for 6 h. After the reaction was complete, the aqueous phase was extracted with toluene, and the resulting organic phase was dried over anhydrous sodium sulfate. The organic phase was then purified by rotary evaporation under reduced pressure and column chromatography (n-hexane:dichloromethane = 15:1) to give a yellow solid (2.21 g, 86% yield).

[0193] 1H NMR (500MHz, CDCl3) δ7.02 (td, J=2.01, 7.42Hz, 1H), 7.08 (dd, J=2.00, 7.49Hz, 1H), 7.18-7.30 (m, 7H), 7. 34(dd,J=2.00,7.52Hz,1H),7.41-7.48(m,3H),7.50-7.62(m,6H),7.63-7.76(m,5H),7.86-7.94(m,2H).

[0194] M / Z: Experimental value, 515.2396; Theoretical value, 514.1933.

[0195] Synthesis Example 11: Synthesis of Compound H45

[0196]

[0197] (a) Under a nitrogen atmosphere, bromobenzene (10 mmol, 1.57 g), phenothiazine (11 mmol, 2.19 g), Pd(OAc)₂ (0.25 mmol, 0.056 g), tri-tert-butylphosphine tetrafluoroborate (0.75 mmol, 0.218 g), and sodium tert-butoxide (20 mmol, 1.92 g) were added to a 250 mL round-bottom flask. The reaction was carried out under reflux (120 °C) for 24 h with toluene (100 mL) as solvent. After the reaction was completed, the mixture was quenched with water, and the aqueous phase was extracted with toluene. The resulting organic phase was dried over anhydrous sodium sulfate, evaporated under reduced pressure, and finally purified by column chromatography (n-hexane:dichloromethane = 10:1) to give a pale yellow solid, namely intermediate 1 (2.2 g, yield 80%).

[0198] 1 H NMR (500MHz, CDCl3) δ6.92 (dd, J=2.04, 7.42Hz, 2H), 7.00 (tt, J=2.24, 7.45Hz, 3H), 7.11 (td, J=1.95 ,7.51Hz,2H),7.24(t,J=7.50Hz,2H),7.38(dd,J=1.90,7.50Hz,2H),7.52(dd,J=1.94,7.41Hz,2H).

[0199] (b) Under a nitrogen atmosphere, in a 250 mL round-bottom flask, intermediate 1 (10 mmol, 2.75 g) was dissolved in 60 mL of a mixed solution of acetic acid and chloroform (Vacetic acid:Vchloroform = 1:1). N-bromosuccinimide (21 mmol, 3.74 g) was added in portions, and the reaction was allowed to proceed for 6 h. The pH was then adjusted to neutral, and the mixture was extracted with ethyl acetate and dried over anhydrous Na2SO4 to obtain the crude product. The crude product was recrystallized from dichloromethane and methanol to give a reddish-brown solid, which was intermediate 2 (0.65 g, yield 15%).

[0200] 1 H NMR(500MHz, CDCl3) δ6.80(d,J=7.49Hz,2H),7.00(tt,J=2.02,7.39Hz,1H),7.17(dd,J =2.00,7.50Hz,2H),7.24(t,J=7.48Hz,2H),7.39-7.46(m,2H),7.57(d,J=2.07Hz,2H).

[0201] (c) Under a nitrogen atmosphere, intermediate 2 (11 mmol, 4.76 g), quinoxaloline-6-boronic acid (10 mmol, 1.74 g), tetrakis(triphenylphosphine)palladium (0.1 mmol, 116 mg), and potassium carbonate (20 mmol, 2.76 g) were added to a 100 mL round-bottom flask, along with 50 mL of toluene, 5 mL of ethanol, and 5 mL of water. The mixture was refluxed at 85 °C for 6 h. After the reaction was complete, the aqueous phase was extracted with toluene, and the resulting organic phase was dried over anhydrous sodium sulfate. The organic phase was then purified by rotary evaporation under reduced pressure and column chromatography (n-hexane:dichloromethane = 15:1) to give a yellow solid, intermediate 3 (4.1 g, 85% yield).

[0202] 1 H NMR (500MHz, CDCl3) δ6.83 (d, J=7.42Hz, 1H), 7.00 (tt, J=2.02, 7.40Hz, 1H), 7.10 (d, J=7.48Hz,1H),7.19(dd,J=2.01,7.51Hz,1H),7.22-7.28(m,2H),7.41(dd,J=2.01,7 .51Hz,1H),7.43-7.50(m,2H),7.59(d,J=2.16Hz,1H),7.78(d,J=1.99Hz,1H),8.11( dd,J=1.47,7.51Hz,1H),8.31(d,J=7.51Hz,1H),8.48(d,J=1.65Hz,1H),8.78(s,2H).

[0203] (d) Under a nitrogen atmosphere, intermediate 3 (5 mmol, 2.41 g), 4-benzoylphenylboronic acid (6 mmol, 1.36 g), tetrakis(triphenylphosphine)palladium (0.1 mmol, 116 mg), and potassium carbonate (10 mmol, 1.38 g) were added to a 100 mL round-bottom flask, along with 50 mL of toluene, 5 mL of ethanol, and 5 mL of water. The mixture was refluxed at 85 °C for 6 h. After the reaction was complete, the aqueous phase was extracted with toluene, and the resulting organic phase was dried over anhydrous sodium sulfate. The organic phase was then purified by rotary evaporation under reduced pressure and column chromatography (n-hexane:dichloromethane = 5:1) to give a white solid, intermediate 4 (2.42 g, 83% yield).

[0204] 1 H NMR (500MHz, CDCl3) δ7.00(tt,J=2.03,7.40Hz,1H),7.12(dd,J=2.90,7.43Hz,2H),7.24(t,J=7.43Hz,2H),7.35-7.57(m,7H),7.70(dd,J=1.52,7.66 Hz,4H),7.79(dd,J=1.98,9.88Hz,2H),7.85-7.92(m,2H),8.12(dd,J=1.46 ,7.48Hz,1H),8.32(d,J=7.45Hz,1H),8.49(d,J=1.39Hz,1H),8.78(s,2H).

[0205] (e) Intermediate product 4 (2 mmol, 1.17 g) was placed in a 50 mL single-necked flask, and dichloromethane (10 mL) and glacial acetic acid (5 mL) were added. The mixture was stirred for 10 min, and then 30% hydrogen peroxide solution (2 mL) was slowly added. The mixture was heated to reflux at 60 °C for 24 h. After the reaction was completed, the pH was adjusted to neutral, and the mixture was extracted with dichloromethane. Then, column chromatography was performed to purify the product using a mixed solvent of petroleum ether and dichloromethane (petroleum ether: dichloromethane = 1:1) as the eluent. Recrystallization was then performed to obtain a white solid powder (1.05 g, yield 85%).

[0206] 1 H NMR (500MHz, CDCl3) δ7.00(tt,J=2.00,7.34Hz,1H),7.24(t,J=7.44Hz,2H),7.45(t,J=7.38Hz,2H),7.52(dt,J=1.82,7.50Hz,3H) ,7.59-7.75(m,8H),7.89(d,J=7.55Hz,2H),8.13(dd,J=1.46,7.49Hz,1H),8.32(d,J=7.52Hz,1H),8.45-8.54(m,3H),8.78(s,2H).

[0207] M / Z: Experimental value, 616.3295; Theoretical value, 615.1617.

[0208] Synthesis Example 12: Synthesis of Compound H52

[0209]

[0210] (a) Under a nitrogen atmosphere, bromobenzene (10 mmol, 1.57 g), 2-bromo-10H-phenthiazide (11 mmol, 3.06 g), Pd(OAc)₂ (0.25 mmol, 0.056 g), tri-tert-butylphosphine tetrafluoroborate (0.75 mmol, 0.218 g), and sodium tert-butoxide (20 mmol, 1.92 g) were added to a 250 mL round-bottom flask. The reaction was carried out under reflux (120 °C) for 24 h with toluene (100 mL) as solvent. After the reaction was completed, the mixture was quenched with water, and the aqueous phase was extracted with toluene. The resulting organic phase was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The solid obtained was purified by column chromatography (n-hexane:dichloromethane = 10:1) to give a pale yellow solid, namely intermediate 1 (2.48 g, yield 70%).

[0211] 1 H NMR (500MHz, CDCl3) δ6.92 (dd, J = 2.00, 7.33Hz, 1H), 6.98-7.02 (m, 2H), 7.05-7.15 (m, 3H), 7.2 4(t,J=7.51Hz,2H),7.29(d,J=7.35Hz,1H),7.34-7.41(m,2H),7.52(dd,J=2.09,7.45Hz,1H).

[0212] (b) Under a nitrogen atmosphere, intermediate 1 (10 mmol, 3.54 g), furan-2-boronic acid (12 mmol, 1.34 g), tetrakis(triphenylphosphine)palladium (0.1 mmol, 116 mg), and potassium carbonate (20 mmol, 2.76 g) were added to a 100 mL round-bottom flask, along with 50 mL of toluene, 5 mL of ethanol, and 5 mL of water. The mixture was refluxed at 85 °C for 6 h. After the reaction was complete, the aqueous phase was extracted with toluene, and the resulting organic phase was dried over anhydrous sodium sulfate. The organic phase was then purified by rotary evaporation under reduced pressure and column chromatography (n-hexane:dichloromethane = 15:1) to give a yellow solid, intermediate 2 (2.73 g, 80% yield).

[0213] 1H NMR (500MHz, CDCl3) δ6.61(t,J=7.40Hz,1H),6.93(dd,J=2.00,7.33Hz,1H),6.96-7.07(m,3H),7.11(td,J=2.11,7.46H z,1H),7.20-7.28(m,3H),7.29(d,J=2.04Hz,1H),7.44-7.50(m,2H),7.50-7.59(m,2H),7.77(dd,J=1.48,7.47Hz,1H).

[0214] (c) Under a nitrogen atmosphere, intermediate 2 (2 mmol, 0.68 g) and anhydrous aluminum chloride (2.4 mmol, 0.32 g) were stirred in anhydrous dichloromethane (30 mL) in a 100 mL round-bottom flask. Benzoyl chloride (2.4 mmol, 0.34 g) was added to the reaction system under ice-water bath conditions. The mixture was heated to reflux at 40 °C for 6 hours. After the reaction was completed, the reaction solution was poured into 10 mL of 10% (v / v) ice-cold dilute hydrochloric acid aqueous solution (i.e., hydrochloric acid aqueous solution at 0 °C). The solution was extracted three times with dichloromethane, evaporated under reduced pressure, and finally purified by column chromatography (dichloromethane: n-hexane = 1:2) to obtain a yellow-green solid, namely intermediate 3 (0.45 g, yield 51%).

[0215] 1 H NMR (500MHz, CDCl3) δ6.48(t,J=7.49Hz,1H),6.83(dd,J=1.46,7.48Hz,1H),6.95(dd,J=2.03,7.37Hz,1H),6.96-7.06(m,2 H),7.12(td,J=2.01,7.51Hz,1H),7.24(t,J=7.44Hz,2H),7.36(s,1H),7.41-7.57(m,7H),7.63-7.70(m,2H),7.90(s,1H).

[0216] (d) Intermediate product 3 (2 mmol, 0.89 g) was placed in a 50 mL single-necked flask, and dichloromethane (10 mL) and glacial acetic acid (5 mL) were added. The mixture was stirred for 10 min, and then 30% hydrogen peroxide solution (2 mL) was slowly added. The mixture was heated to reflux at 60 °C for 24 h. After the reaction was completed, the pH was adjusted to neutral, and the mixture was extracted with dichloromethane. Then, column chromatography was performed to purify the product using a mixed solvent of petroleum ether and dichloromethane (petroleum ether: dichloromethane = 1:1) as the eluent. Recrystallization was then performed to obtain a white solid powder (0.82 g, yield 86%).

[0217] 1¹H NMR (500MHz, CDCl₃) δ 6.51 (t, J = 7.51Hz, 1H), 6.88 (dd, J = 1.57, 7.38Hz, 1H), 7.00 (tt, J = 1.98, 7.32Hz, 1H), 7.21–7.28 (m, 3H), 7.37 (td, J = 2.01, 7.50Hz, 1H), 7.43–7.47 (m, 3H), 7.51–7.55 (m, 4H), 7.61–7.70 (m, 3H), 8.11 (dd, J = 2.02, 7.37Hz, 1H), 8.69 (s, 1H). M / Z: Experimental value, 478.3654; Theoretical value, 477.1035.

[0218] Other compounds in this application can be synthesized by selecting suitable starting materials according to the above synthetic examples, or by selecting any other suitable method and starting materials.

[0219] Example 1

[0220] A glass substrate 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 to obtain a glass substrate with an anode.

[0221] Then, the glass substrate with the anode was placed in a vacuum chamber and evacuated to a vacuum level of less than 10. -5 A hole injection layer is vacuum-deposited onto the anolyte layer of the aforementioned glass substrate with an anode. The hole injection layer material comprises 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 total film thickness is 10 nm. The hole injection layer material HT-11 and p-type dopant p-1 are as follows:

[0222]

[0223] Then, hole transport material HT-12 was vacuum-deposited on the hole injection layer as a hole transport layer, wherein the deposition rate was 0.1 nm / s and the deposition film thickness was 80 nm. The hole transport material HT-12 is as follows:

[0224]

[0225] Then, a light-emitting layer is vacuum-deposited on the hole transport layer. The light-emitting layer includes a host material H3 and a guest material BD-1. The deposition is performed using a multi-source co-evaporation method. The deposition rate of the host material H3 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 H3. The total film thickness is 30 nm. The host material H3 and the guest material BD-1 are as follows:

[0226]

[0227] Then, electron transport material ET-8 is vacuum-deposited on top of the light-emitting layer as an electron transport layer, wherein the deposition rate is 0.1 nm / s and the deposition film thickness is 30 nm; the electron transport material ET-8 is as follows:

[0228]

[0229] Then, a 10 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.

[0230] Finally, an Al layer with a thickness of 150 nm was vacuum-deposited on the electron injection layer as the cathode electrode of the organic electroluminescent device, wherein the deposition rate was 0.1 nm / s.

[0231] Example 2-12

[0232] Except that the main material of the light-emitting layer is replaced by compounds H4, H8, H10, H15, H25, H36, H37, H38, H44, H45, and H52 instead of compound H3, the rest is the same as in Example 1. See Table 1 for details.

[0233] Comparative Example 1

[0234] Except for the use of BH-A as the main material for the light-emitting layer, the rest is the same as in Example 1; BH-A is as follows:

[0235]

[0236] The organic electroluminescent devices prepared by the above process were subjected to the following performance measurements:

[0237] Under the same brightness, the driving voltage, current efficiency, and lifetime of the organic electroluminescent devices prepared in Examples 1-12 and Comparative Example 1 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 1000.00 cd / m². 2The voltage at that time is the driving voltage, and the current density at that time is measured simultaneously; the ratio of brightness to current density is the current efficiency; the life test of LT95 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. The results are shown in Table 1.

[0238] Table 1 Performance results of organic electroluminescent devices

[0239]

[0240] As shown in Table 1, compounds H3, H4, H8, H10, H15, H25, H36, H37, H38, H44, H45, and H52 prepared in this application, when used as the host materials for the light-emitting layer in organic electroluminescent devices, exhibit significantly lower driving voltage, higher current efficiency, and longer LT95 lifetime compared to Comparative Example 1. The results demonstrate that the compounds provided in this application, when used as the host materials for the light-emitting layer in organic electroluminescent devices, can effectively reduce driving voltage, improve current efficiency, and extend device lifespan, making them high-performance host materials for the light-emitting layer.

[0241] 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 should be included within the scope of protection of this application.

Claims

1. A blue light-emitting layer substrate material, comprising a compound selected from: 。 2. An organic electroluminescent device comprising at least one of the blue light emitting layer host materials as described in claim 1.

3. A display device comprising the organic electroluminescent device of claim 2.

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