Compound, luminescent layer host material and organic electroluminescent device

Abstract

The invention provides a compound as shown in a formula (I), a luminescent layer host material containing the compound, an organic electroluminescent device and a display device. The compound is high in stability and good in film-forming property, electron-donating and electron-withdrawing groups are introduced into the compound, the compound serves as a bipolar light-emitting layer main body material, the characteristics of hole and electron transmission can be balanced, the device structure is simplified, preparation of the organic light-emitting device is facilitated, the light-emitting efficiency of the organic light-emitting device is improved, and the service life of the organic light-emitting device is prolonged. The organic electroluminescent device provided by the invention comprises the compound provided by the invention as a luminescent layer main body material, and has lower driving voltage, better luminous efficiency and longer service life. The display device provided by the invention has an excellent display effect. # imgabs0 #

Description

Technical Field

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

[0002] The development of mankind and society cannot be separated from light, especially luminescent materials. Luminescent materials are divided into inorganic luminescent materials and organic luminescent materials. Compared with inorganic luminescent materials, organic luminescent materials are favored by researchers because of their many types, easy adjustment of emission wavelengths, and relatively flexible molecular design. In recent years, with the progress and development of science and technology, organic electroluminescent (OLEDs) devices have gradually entered the market due to their advantages such as fast response speed, high luminous efficiency, and wide viewing angle. OLEDs devices are composed of substrates, cathodes, anodes, hole injection layers, electron injection layers, hole transport layers, electron transport layers, electron blocking layers, hole blocking layers, and luminescent layers. Among them, the luminescent layer is the core part of OLEDs devices and plays a vital role in the performance and life of OLEDs devices. Therefore, designing and synthesizing efficient luminescent layer main materials has become the main content of current research. Summary of the invention

[0003] The purpose of the present application is to provide a compound which, when used as a main material of a light-emitting layer, can improve the luminous efficiency and extend the service life of an organic electroluminescent device.

[0004] In a first aspect, the present application provides a compound represented by formula (I):

[0005]

[0006] Among them, R 1 -R 5 are each independently selected from hydrogen, deuterium, C1-C6 alkyl, C1-C6 alkenyl which is unsubstituted or substituted by Ra, C6-C 30 Aryl, unsubstituted or substituted C3-C 30 Heteroaryl, R 1 and R 2 can be connected to form a ring, R 3 and R 5 Can be connected to form a ring;

[0007] A is selected from C6-C 30 Aryl, unsubstituted or substituted C3-C 18 heteroaryl;

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

[0009] X 1 Selected from CR 6 or N, R 6 is selected from hydrogen, deuterium, C1-C6 alkyl, C6-C 30 Aryl, unsubstituted or substituted C3-C 18 Heteroaryl, R 6 and A can be connected to form a ring;

[0010] X 2 Selected from CR 7 R 8 , O or SO2, R 7 and R 8 are each independently selected from hydrogen, deuterium, C1-C6 alkyl, C6-C6 unsubstituted or substituted by Ra 30 Aryl, unsubstituted or substituted C3-C 30 Heteroaryl, R 7 and R 8 Can be connected to form a ring;

[0011] L is selected from a chemical bond, an unsubstituted or Ra-substituted C6-C 30 Arylene, unsubstituted or substituted C3-C 30 heteroarylene;

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

[0013] The Ra are each independently selected from deuterium, halogen, nitro, cyano, C1-C4 alkyl, phenyl, biphenyl, naphthyl, C1-C4 haloalkyl, quinoxalinyl, quinolyl, pyridyl or benzofuranyl.

[0014] The second aspect of the present application provides a light-emitting layer host material, which comprises at least one of the compounds provided in the first aspect of the present application.

[0015] The third aspect of the present application provides an organic electroluminescent device, which comprises at least one of the light-emitting layer host materials provided in the second aspect of the present application.

[0016] A fourth aspect of the present application provides a display device, which includes the organic electroluminescent device provided by the third aspect of the present application.

[0017] The compounds provided in the present application have high stability and good film-forming properties. The compounds introduce electron-donating and electron-withdrawing groups as the main materials of the bipolar light-emitting layer, which can balance the characteristics of hole and electron transmission, simplify the device structure, facilitate the preparation of organic electroluminescent devices, and improve the luminous efficiency and service life of organic electroluminescent devices. The organic electroluminescent device provided in the present application contains the compounds of the present application as the main materials of the light-emitting layer, and has lower driving voltage, better luminous efficiency and longer service life. The display device provided in the present application has excellent display effect.

[0018] Of course, implementing any product or method of the present application does not necessarily require achieving all of the advantages described above at the same time. BRIEF DESCRIPTION OF THE DRAWINGS

[0019] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the drawings required for use in the description of the embodiments will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present application. For ordinary technicians in this field, other embodiments can also be obtained based on these drawings.

[0020] Figure 1 A schematic diagram of the structure of a typical organic electroluminescent device. DETAILED DESCRIPTION

[0021] The following will be combined with the drawings in the embodiments of the present application to clearly and completely describe the technical solutions in the embodiments of the present application. Obviously, the described embodiments are only part of the embodiments of the present application, rather than all the embodiments. All other embodiments obtained by those skilled in the art based on the present application belong to the scope of protection of the present application.

[0022] In a first aspect, the present application provides a compound represented by formula (I):

[0023]

[0024] Among them, R 1 -R 5 are each independently selected from hydrogen, deuterium, C1-C6 alkyl, C1-C6 alkenyl which is unsubstituted or substituted by Ra, C6-C 30 Aryl, unsubstituted or substituted C3-C 30 Heteroaryl, R 1 and R 2 can be connected to form a ring, R 3 and R 5 Can be connected to form a ring;

[0025] A is selected from C6-C 30Aryl, unsubstituted or substituted C3-C 18 heteroaryl;

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

[0027] X 1 Selected from CR 6 or N, R 6 is selected from hydrogen, deuterium, C1-C6 alkyl, C6-C 30 Aryl, unsubstituted or substituted C3-C 18 Heteroaryl, R 6 and A can be connected to form a ring;

[0028] X 2 Selected from CR 7 R 8 , O or SO2, R 7 and R 8 are each independently selected from hydrogen, deuterium, C1-C6 alkyl, C6-C6 unsubstituted or substituted by Ra 30 Aryl, unsubstituted or substituted C3-C 30 Heteroaryl, R 7 and R 8 Can be connected to form a ring;

[0029] L is selected from a chemical bond, an unsubstituted or Ra-substituted C6-C 30 Arylene, unsubstituted or substituted C3-C 30 heteroarylene;

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

[0031] The Ra are each independently selected from deuterium, halogen, nitro, cyano, C1-C4 alkyl, phenyl, biphenyl, naphthyl, C1-C4 haloalkyl, quinoxalinyl, quinolyl, pyridyl or benzofuranyl.

[0032] Preferably, R 1 -R 5R is independently selected from hydrogen, deuterium, methyl, ethyl, propyl, vinyl, propenyl, butenyl, a group of the following compounds which are unsubstituted or substituted with 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, 1 and R 2 can be connected to form a ring, R 3 and R 5 Can be connected to form a ring.

[0033] Preferably, A is selected from the group of the following compounds which are unsubstituted or substituted with 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, a radical of the following compounds which are unsubstituted or substituted with 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.

[0035] Preferably, X 1 Selected from CR 6 or N, R 6 a radical selected from hydrogen, deuterium, methyl, ethyl, propyl, a radical selected from the following compounds which are unsubstituted or substituted with 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, R 6 and A can be connected to form a ring.

[0036] Preferably, X 2 Selected from CR 7 R 8 , O or SO2, R 7 and R 8each independently selected from hydrogen, deuterium, methyl, ethyl, propyl, a group of the following compounds which are unsubstituted or substituted with Ra: 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 Can be connected to form a ring.

[0037] Preferably, L is selected from a chemical bond, a subunit of the following compounds which is unsubstituted or substituted by Ra: benzene, biphenyl, naphthalene, phenanthrene, pyrene, fluorene, spirofluorene, imidazole.

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

[0039] Preferably, the Ra are each independently selected from deuterium, fluorine, chlorine, bromine, nitro, cyano, methane, ethane, propane, n-butane, isobutane, phenyl, biphenyl, naphthyl, monofluoromethane, monochloromethane, difluoromethane, dichloromethane, trifluoromethane, trichloromethane, quinoxalinyl, quinolyl, pyridyl or benzofuranyl.

[0040] The compounds provided in the present application have high stability and good film-forming properties. The compounds introduce electron-donating and electron-withdrawing groups as the main materials of the bipolar light-emitting layer, which can balance the characteristics of hole and electron transmission, simplify the device structure, facilitate the preparation of organic electroluminescent devices, and improve the luminous efficiency and service life of organic electroluminescent devices.

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

[0042]

[0043] in,

[0044] R 3 -R 5 , R 9 -R 12 are each independently selected from hydrogen, deuterium, C1-C6 alkyl, C6-C6 unsubstituted or substituted by Ra 18 Aryl, unsubstituted or substituted C3-C 18 Heteroaryl, R 3 and R 5 Can be connected to form a ring;

[0045] A is selected from C6-C 30Aryl, unsubstituted or substituted C3-C 18 heteroaryl;

[0046] B is selected from C3-C6 cycloalkyl, unsubstituted or substituted C6-C 18 Aryl, unsubstituted or substituted C3-C 18 heteroaryl;

[0047] L is selected from a chemical bond, an unsubstituted or Ra-substituted C6-C 18 Arylene, unsubstituted or substituted C3-C 10 heteroarylene;

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

[0049] The Ra are each independently selected from deuterium, halogen, nitro, cyano, C1-C4 alkyl, phenyl, biphenyl, naphthyl, C1-C4 haloalkyl, quinoxalinyl, quinolyl, pyridyl or benzofuranyl.

[0050] Preferably, R 3 -R 5 , R 9 -R 12 each independently selected from hydrogen, deuterium, methyl, ethyl, propyl, a group of the following compounds which are unsubstituted or substituted with Ra: 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 Can be connected to form a ring.

[0051] Preferably, A is selected from the group of the following compounds which are unsubstituted or substituted with 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, a radical of the following compounds which are unsubstituted or substituted with Ra: 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 a chemical bond, a subunit of the following compounds which is unsubstituted or substituted by Ra: benzene, biphenyl, naphthalene, phenanthrene, pyrene, fluorene, imidazole.

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

[0055] Preferably, the Ra are each independently selected from deuterium, fluorine, chlorine, bromine, nitro, cyano, methane, ethane, propane, n-butane, isobutane, phenyl, biphenyl, naphthyl, monofluoromethane, monochloromethane, difluoromethane, dichloromethane, trifluoromethane, trichloromethane, quinoxalinyl, quinolyl, pyridyl or benzofuranyl.

[0056] Preferably, the compound provided by the present application contains both donor units and acceptor units in the molecular structure of the compound. The dual introduction of donor units such as sulfur atoms and oxygen atoms and acceptor units such as carbonyl groups and double bond sulfur can greatly enhance the luminescence intensity. At the same time, by oxidizing sulfur to sulfone, non-radiative enhancement can also obtain a host material with different luminescent colors.

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

[0058]

[0059]

[0060]

[0061] The second aspect of the present application provides a light-emitting layer host material, which comprises at least one of the compounds provided in the first aspect of the present application.

[0062] When the compound of the present application is used as a main material of the light-emitting layer, as a main material of the bipolar light-emitting layer, it can balance the characteristics of hole and electron transmission, simplify the device structure, facilitate the preparation of organic electroluminescent devices, and improve the luminous efficiency and service life of organic electroluminescent devices.

[0063] The third aspect of the present application provides an organic electroluminescent device, which comprises at least one of the luminescent layer host materials provided in the second aspect of the present application. Therefore, the organic electroluminescent device provided by the present application has a lower driving voltage, better luminous efficiency and longer service life.

[0064] In the present application, there is no particular limitation on the type and structure of the organic electroluminescent device, and it can be an organic electroluminescent device of different types and structures known in the art, as long as at least one of the main materials of the light-emitting layer provided in the present application can be used.

[0065] In some embodiments of the present application, the organic electroluminescent device of the present application may be a light-emitting device with a top-emitting structure, which may include, in sequence, an 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 on a substrate.

[0066] The organic electroluminescent device of the present application may also be a light-emitting device with a bottom emission 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 cathode structure in sequence on a substrate.

[0067] The organic electroluminescent device of the present application may also be a light-emitting device with a double-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 in sequence on a substrate.

[0068] In addition, the organic electroluminescent device of the present 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 may be provided on the transparent electrode on the light-emitting side. However, the structure of the organic electroluminescent device of the present application is not limited to the above-mentioned specific structure. If necessary, the above-mentioned layers may be omitted or increased. The present application has no particular restrictions on the thickness of the above-mentioned layers, as long as the purpose of the present application can be achieved. For example, the organic electroluminescent device may 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 in sequence. Exemplarily, Figure 1 A schematic diagram of a typical organic electroluminescent device is shown, wherein, 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 in sequence.

[0069] Understandably, Figure 1 The structure of a typical organic electroluminescent device is only schematically shown, and the present application is not limited to this structure. The main material of the light-emitting layer of the present application can be used for any type of organic electroluminescent device.

[0070] For convenience, the following reference Figure 1The organic electroluminescent device of the present application is described, but this does not mean any limitation on the protection scope of the present application. It can be understood that all organic electroluminescent devices that can use the luminescent layer host material of the present application are within the protection scope of the present application.

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

[0072] In the present application, the material of the reflective anode electrode 2 is not particularly limited, and can be selected from transparent conductive materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO) known in the prior art, or metal materials such as silver and its alloys, aluminum and its alloys, or organic conductive materials such as poly (3,4-ethylenedioxythiophene) (PEDOT), or the reflective anode electrode 2 is a multilayer structure formed by the above materials. The present application does not particularly limit the number of layers of its multilayer structure, and can be selected according to actual needs, as long as the purpose of the present application can be achieved, for example, 1 layer, 2 layers, 3 layers or more layers.

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

[0074] In the present application, the hole injection layer 3 may further include a p-type dopant. The present application has no particular restrictions on the type of the p-type dopant, and various p-type dopants known in the art may be used. For example, the p-type dopant may be selected from but not limited to at least one of the following p-1 to p-3 compounds:

[0075]

[0076] In the present application, the amount of the p-type dopant is not particularly limited and may be an amount known to those skilled in the art.

[0077] In the present 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 can meet the purpose of the present application, for example, 1 layer, 2 layers, 3 layers, 4 layers or more layers.

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

[0079]

[0080]

[0081] In the present application, the light-emitting layer 5 may include a blue light-emitting layer, a green light-emitting layer or a red light-emitting layer, and 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 the present application, the light-emitting layer host material includes at least one of the light-emitting layer host materials of the present application.

[0083] In the present application, the amount of the host material of the light-emitting layer is not particularly limited and can be an amount known to those skilled in the art.

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

[0085]

[0086] In the present application, the amount of the guest material in the light-emitting layer is not particularly limited and can be an amount known to those skilled in the art.

[0087] In the present 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 present application does not particularly limit the number of layers of the electron transport layer 6, and can be adjusted according to actual needs, as long as it can meet the purpose of the present application, for example, 1 layer, 2 layers, 3 layers, 4 layers or more layers.

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

[0089]

[0090]

[0091]

[0092] In the present application, the electron transport layer 6 may further include an n-type dopant. The present application has no particular limitation on the type of the n-type dopant, and various n-type dopants known in the art may be used, for example, the following n-type dopants may be used:

[0093]

[0094] In the present application, the amount of the n-type dopant is not particularly limited and can be an amount known to those skilled in the art.

[0095] In the present 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 materials in the prior art such as 8-hydroxyquinoline lithium (LiQ), LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, etc.

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

[0097] The method for preparing the organic electroluminescent device of the present application is not particularly limited, and any method known in the art may be used. For example, the present application may be prepared by the following preparation method:

[0098] (1) cleaning the reflective anode electrode 2 on the top-emitting OLED device substrate 1 by using a cleaning machine through steps such as chemical cleaning, water cleaning, brushing, high-pressure water cleaning, and air knife cleaning, and then performing a heat treatment;

[0099] (2) vacuum evaporating a hole injection material on the reflective anode electrode 2 to form a hole injection layer 3;

[0100] (3) vacuum evaporating a hole transport material on the hole injection layer 3 to form a hole transport layer 4;

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

[0102] (5) vacuum evaporating an electron transport material on the light emitting layer 5 to form an electron transport layer 6;

[0103] (6) vacuum evaporating an electron injection material on the electron transport layer 6 to form an electron injection layer 7;

[0104] (7) A cathode material is vacuum-deposited on the electron injection layer 7 to form a cathode electrode 8 .

[0105] The above only describes a typical structure of an organic electroluminescent device and its preparation method. It should be understood that the present application is not limited to this structure. The luminescent layer host material of the present application can be used for an organic electroluminescent device of any structure, and the organic electroluminescent device can be prepared by any preparation method known in the art.

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

[0107] The synthesis method of the compound of the present application is not particularly limited, and any method known to those skilled in the art can be used for synthesis. The following examples illustrate the synthesis process of the compound of the present application. As used herein, room temperature / normal temperature refers to 25±5°C.

[0108] Synthesis example

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

[0110]

[0111] (a) In a 100 mL round-bottom flask under 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 and reacted at reflux (120°C) for 24 h with toluene (50 mL) as solvent. After the reaction was completed, water was added to quench the reaction, and the aqueous phase was extracted with toluene. The obtained organic phase was dried over anhydrous sodium sulfate (Na2SO4) and evaporated under reduced pressure. The obtained solid was purified by column chromatography (n-hexane: dichloromethane = 10:1) to obtain a light yellow solid, i.e., 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, the intermediate product 1 (10 mmol, 3.75 g) was dissolved in tetrahydrofuran (THF, 50 mL), and a THF solution (10 mL) containing N-bromosuccinimide (NBS, 11 mmol, 1.96 g) was added in batches under a nitrogen atmosphere at 0°C. The reaction process was monitored by thin layer chromatography. After the reaction was completed, water was added to quench the reaction, and the mixture was 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, namely the intermediate product 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 nitrogen atmosphere, intermediate 2 (5 mmol, 2.27 g), 4-benzoylphenylboronic acid (6 mmol, 1.36 g), tetrakistriphenylphosphine 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, and 50 mL of toluene, 5 mL of ethanol and 5 mL of water were added, and refluxed at 85°C for 6 h. After the reaction was completed, the aqueous phase was extracted with toluene, and the obtained organic phase was dried over anhydrous sodium sulfate. Then, it was purified by vacuum rotary evaporation and column chromatography (n-hexane: dichloromethane = 5:1) to obtain a white solid (2.36 g, yield 85%).

[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: Exp., 556.0136; Calc., 555.2198.

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

[0119]

[0120] (a) Under 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, and the mixture was reacted under reflux (120° C.) with toluene (100 mL) as solvent for 24 h. After the reaction was completed, water was added to quench the reaction, and the aqueous phase was extracted with toluene. The obtained organic phase was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The obtained solid was purified by column chromatography (n-hexane: dichloromethane = 10:1) to obtain a light 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 nitrogen atmosphere, the intermediate product 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, and benzoyl chloride (2.4 mmol, 0.34 g) was added to the reaction system under ice-water bath conditions, and heated to reflux at 40°C for 6 hours. After the reaction was completed, the reaction solution was poured into 10 mL of a 10% by volume glacial hydrochloric acid-water solution (i.e., a 0°C hydrochloric acid aqueous solution), extracted with dichloromethane three times, and evaporated under reduced pressure. Finally, it was purified by column chromatography (dichloromethane:n-hexane=1:2) to obtain a yellow-green solid, i.e., the intermediate product 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) The 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, a mixed solvent of petroleum ether and dichloromethane (petroleum ether: dichloromethane = 1:1) was used as the eluent for column chromatography separation and purification. The mixture was further recrystallized 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: Exp., 437.2585; Calc., 436.0882.

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

[0128]

[0129] (a) Under 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, and toluene (100 mL) was used as solvent to react under reflux conditions (120° C.) for 24 h. After the reaction was completed, water was added to quench the reaction, and the aqueous phase was extracted with toluene. The obtained organic phase was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The obtained solid was purified by column chromatography (petroleum ether) to obtain a light 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 nitrogen atmosphere, intermediate product 1 (4mmol, 1.49g) and anhydrous aluminum chloride (4.8mmol, 0.635g) were added to a 100mL round-bottom flask, and anhydrous dichloromethane (40mL) was added for stirring. After stirring at room temperature for 15 minutes, benzoyl chloride (4.8mmol, 0.669g) was added to the reaction system under ice-water bath conditions, and heated to reflux at 40°C for 6 hours. After the reaction was completed, the reaction solution was poured into 13mL of 10% glacial hydrochloric acid-water solution (i.e., 0°C hydrochloric acid aqueous solution), extracted with dichloromethane 3 times, evaporated under reduced pressure, and finally purified by column chromatography (n-hexane: dichloromethane = 2:1) to obtain a yellow solid, i.e., intermediate product 2 (1.2g, 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) The 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, stirred for 10 min, and then 30% hydrogen peroxide solution (2 mL) was slowly added, and heated to reflux at 60 ° C for 24 h. After the reaction was completed, the pH was adjusted to neutral, extracted with dichloromethane, and then column chromatography was used as an eluent to separate and purify the mixture, and recrystallization was continued 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: Exp., 512.0375; Calc., 511.1242.

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

[0137]

[0138] (a) Under 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, and the mixture was reacted under reflux (120° C.) with toluene (100 mL) as solvent for 24 h. After the reaction was completed, water was added to quench the reaction, and the aqueous phase was extracted with dichloromethane. The obtained organic phase was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The obtained solid was purified by column chromatography (n-hexane: dichloromethane = 10:1) to obtain a light 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 nitrogen atmosphere, the intermediate product 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, and benzoyl chloride (2.4 mmol, 0.34 g) was added to the reaction system under ice-water bath conditions, and heated to reflux at 40° C. for 6 hours. After the reaction was completed, the reaction solution was poured into 10 mL of a 10% by volume glacial hydrochloric acid-water solution (i.e., a 0° C. hydrochloric acid aqueous solution), extracted with dichloromethane for 3 times, evaporated under reduced pressure, and finally purified by column chromatography (dichloromethane:n-hexane=4:1) to obtain a light yellow solid, i.e., the intermediate product 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) The 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, stirred for 10 min, and then 30% hydrogen peroxide solution (2 mL) was slowly added, and heated to reflux at 60 ° C for 24 h. After the reaction was completed, the pH was adjusted to neutral, extracted with dichloromethane, and then column chromatography was used as an eluent to separate and purify the mixture, and recrystallization was continued 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: Exp., 480.3617; Calc., 479.0803.

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

[0146]

[0147] (a) Under 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, and toluene (100 mL) was used as solvent to react under reflux conditions (120° C.) for 24 h. After the reaction was completed, water was added to quench the reaction, and the aqueous phase was extracted with toluene. The obtained organic phase was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The obtained solid was purified by column chromatography (n-hexane: dichloromethane = 10:1) to obtain a light 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 nitrogen atmosphere, the intermediate product 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, and benzoyl chloride (2.4 mmol, 0.34 g) was added to the reaction system under ice-water bath conditions, and heated to reflux at 40° C. for 6 hours. After the reaction was completed, the reaction solution was poured into 10 mL of a 10% by volume glacial hydrochloric acid-water solution (i.e., a 0° C. hydrochloric acid aqueous solution), extracted with dichloromethane for 3 times, evaporated under reduced pressure, and finally purified by column chromatography (dichloromethane:n-hexane=1:1) to obtain a light yellow solid, i.e., the intermediate product 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) The 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, stirred for 10 min, and then 30% hydrogen peroxide solution (2 mL) was slowly added, and heated to reflux at 60 ° C for 24 h. After the reaction was completed, the pH was adjusted to neutral, extracted with dichloromethane, and then column chromatography was used as an eluent using a mixed solvent of petroleum ether and dichloromethane (petroleum ether: dichloromethane = 1:1) for separation and purification, and recrystallization was continued 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: Exp., 414.2215; Calc., 413.0834.

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

[0155]

[0156] (a) Under 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, and toluene (100 mL) was used as solvent to react under reflux conditions (120° C.) for 24 h. After the reaction was completed, water was added to quench the reaction, and the aqueous phase was extracted with toluene. The obtained organic phase was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The obtained solid was purified by column chromatography (n-hexane: dichloromethane = 10:1) to obtain a light 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 nitrogen atmosphere, the intermediate product 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, and benzoyl chloride (2.4 mmol, 0.34 g) was added to the reaction system under ice-water bath conditions, and heated to reflux at 40° C. for 6 hours. After the reaction was completed, the reaction solution was poured into 10 mL of a 10% by volume glacial hydrochloric acid-water solution (i.e., a 0° C. hydrochloric acid aqueous solution), extracted with dichloromethane three times, and evaporated under reduced pressure. Finally, it was purified by column chromatography (dichloromethane:n-hexane=1:1) to obtain a yellow solid, i.e., the intermediate product 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) The 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, stirred for 10 min, and then 30% hydrogen peroxide solution (2 mL) was slowly added, and heated to reflux at 40 ° C for 24 h. After the reaction was completed, the pH was adjusted to neutral, extracted with dichloromethane, and then column chromatography was used as an eluent using a mixed solvent of petroleum ether and dichloromethane (petroleum ether: dichloromethane = 1:1) for separation and purification, and recrystallization was continued 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: Exp., 643.0315; Calc., 642.1726.

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

[0164]

[0165] (a) Under 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, and toluene (100 mL) was used as solvent to react under reflux conditions (120° C.) for 24 h. After the reaction was completed, water was added to quench the reaction, and the aqueous phase was extracted with toluene. The obtained organic phase was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The obtained solid was purified by column chromatography (n-hexane: dichloromethane = 10:1) to obtain a light 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 nitrogen atmosphere, the intermediate product 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, and pyridine-2-carbonyl chloride hydrochloride (6 mmol, 1.07 g) was added to the reaction system under ice-water bath conditions, and heated to reflux at 40° C. for 6 hours. After the reaction was completed, the reaction solution was poured into 16 mL of a 10% by volume glacial hydrochloric acid-water solution (i.e., a 0° C. hydrochloric acid aqueous solution), extracted with dichloromethane three times, evaporated under reduced pressure, and finally purified by column chromatography (dichloromethane:n-hexane=1:1) to obtain a bright yellow solid, i.e., the intermediate product 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) The 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, stirred for 10 min, and then 30% hydrogen peroxide solution (2 mL) was slowly added, and heated to reflux at 60 ° C for 24 h. After the reaction was completed, the pH was adjusted to neutral, extracted with dichloromethane, and then column chromatography was used as an eluent. Purification was performed, and recrystallization was continued 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: Exp., 413.3167; Calc., 412.0882.

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

[0173]

[0174] (a) Under 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, and toluene (100 mL) was used as solvent to react under reflux conditions (120° C.) for 24 h. After the reaction was completed, water was added to quench the reaction, and the aqueous phase was extracted with toluene. The obtained organic phase was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The obtained solid was purified by column chromatography (n-hexane: dichloromethane = 10:1) to obtain a light 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 nitrogen atmosphere, in a 100 mL round-bottom flask, the intermediate product 1 (2.75 g, 10 mmol) was dissolved in 60 mL of a mixed solution of acetic acid and chloroform (V acetic acid: V chloroform = 1:1). N-bromosuccinimide (1.96 g, 11 mmol) was added in batches and reacted at room temperature for 6 h. Afterwards, the pH was adjusted to neutral, extracted with ethyl acetate and dried over anhydrous Na2SO4 to obtain a crude product. The crude product was recrystallized from dichloromethane and methanol to obtain a reddish brown solid, which was the intermediate product 2 (0.7 g, yield 20%).

[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 nitrogen atmosphere, intermediate 2 (3 mmol, 1.06 g), 3-(1H-imidazole-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, and toluene (50 mL) was used as solvent to react under reflux conditions (120° C.) for 24 h. After the reaction was completed, water was added to quench the reaction, and the aqueous phase was extracted with toluene. The obtained organic phase was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The obtained solid was purified by column chromatography (n-hexane: dichloromethane = 5:1) to obtain a light 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) The 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, a mixed solvent of petroleum ether and dichloromethane (petroleum ether: dichloromethane = 1:1) was used as an eluent for column chromatography separation and purification. The mixture was further recrystallized 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: Exp., 479.2139; Calc., 478.1100.

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

[0184]

[0185] (a) Under nitrogen atmosphere, 10H-spiro[acridine-9,9'-oxanthene] (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, and toluene (100 mL) was used as solvent to react under reflux conditions (120° C.) for 24 h. After the reaction was completed, water was added to quench the reaction, and the aqueous phase was extracted with toluene. The obtained organic phase was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The obtained solid was purified by column chromatography (n-hexane: dichloromethane = 10:1) to obtain a light 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 nitrogen atmosphere, the intermediate product 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, and benzoyl chloride (3.6 mmol, 0.51 g) was added to the reaction system under ice-water bath conditions, and heated to reflux at 40°C for 6 hours. After the reaction was completed, the reaction solution was poured into 10 mL of a 10% by volume glacial hydrochloric acid-water solution (i.e., a 0°C hydrochloric acid aqueous solution), extracted with dichloromethane three times, evaporated under reduced pressure, and finally purified by column chromatography (dichloromethane:n-hexane=1:1) to obtain 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: Exp., 528.0115; Calc., 527.1885.

[0190] Synthesis Example 10: Synthesis of Compound H44

[0191]

[0192] Under nitrogen atmosphere, 3-bromo-9,9-diphenyl-9H-xanthene (5mmol, 2.07g), 4-benzoylphenylboronic acid (6mmol, 1.36g), tetrakistriphenylphosphine palladium (0.05mmol, 58mg) and potassium carbonate (10mmol, 1.38g) were added to a 100mL round-bottom flask, and 50mL toluene (tol.), 5mL ethanol and 5mL water were added, and refluxed at 85°C for 6h. After the reaction was completed, the aqueous phase was extracted with toluene, and the obtained organic phase was dried over anhydrous sodium sulfate. After that, it was purified by vacuum rotary evaporation and column chromatography (n-hexane: dichloromethane = 15:1) to obtain a yellow solid (2.21g, yield 86%).

[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: Exp., 515.2396; Calc., 514.1933.

[0195] Synthesis Example 11: Synthesis of Compound H45

[0196]

[0197] (a) Under 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, and toluene (100 mL) was used as solvent to react under reflux conditions (120° C.) for 24 h. After the reaction was completed, water was added to quench the reaction, and the aqueous phase was extracted with toluene. The obtained organic phase was dried over anhydrous sodium sulfate, evaporated under reduced pressure, and finally purified by column chromatography (n-hexane: dichloromethane = 10:1) to obtain a light 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 nitrogen atmosphere, in a 250 mL round-bottom flask, the intermediate product 1 (10 mmol, 2.75 g) was dissolved in 60 mL of a mixed solution of acetic acid and chloroform (V acetic acid: V chloroform = 1:1), and N-bromosuccinimide (21 mmol, 3.74 g) was added in batches and reacted for 6 h. Afterwards, the pH was adjusted to neutral, extracted with ethyl acetate and dried over anhydrous Na2SO4 to obtain a crude product. The crude product was recrystallized from dichloromethane and methanol to obtain a reddish brown solid, which was the intermediate product 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 nitrogen atmosphere, intermediate product 2 (11mmol, 4.76g), quinoxaline-6-boronic acid (10mmol, 1.74g,), tetrakistriphenylphosphine palladium (0.1mmol, 116mg) and potassium carbonate (20mmol, 2.76g) were added to a 100mL round-bottom flask, and 50mL toluene, 5mL ethanol and 5mL water were added, and refluxed at 85°C for 6h. After the reaction was completed, the aqueous phase was extracted with toluene, and the obtained organic phase was dried over anhydrous sodium sulfate. Then, it was purified by vacuum rotary evaporation and column chromatography (n-hexane: dichloromethane = 15:1) to obtain a yellow solid, namely intermediate product 3 (4.1g, yield 85%).

[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 nitrogen atmosphere, intermediate 3 (5mmol, 2.41g), 4-benzoylphenylboronic acid (6mmol, 1.36g), tetrakistriphenylphosphine palladium (0.1mmol, 116mg) and potassium carbonate (10mmol, 1.38g) were added to a 100mL round-bottom flask, and 50mL toluene, 5mL ethanol and 5mL water were added, and refluxed at 85°C for 6h. After the reaction was completed, the aqueous phase was extracted with toluene, and the obtained organic phase was dried over anhydrous sodium sulfate. Then, it was purified by vacuum rotary evaporation and column chromatography (n-hexane: dichloromethane = 5:1) to obtain a white solid, namely intermediate 4 (2.42g, yield 83%).

[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) The 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, a mixed solvent of petroleum ether and dichloromethane (petroleum ether: dichloromethane = 1:1) was used as an eluent for column chromatography separation and purification. The mixture was further recrystallized 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: Exp., 616.3295; Calc., 615.1617.

[0208] Synthesis Example 12: Synthesis of Compound H52

[0209]

[0210] (a) Under nitrogen atmosphere, bromobenzene (10 mmol, 1.57 g), 2-bromo-10H-phenothiazine (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, and toluene (100 mL) was used as solvent to react under reflux conditions (120° C.) for 24 h. After the reaction was completed, water was added to quench the reaction, and the aqueous phase was extracted with toluene. The obtained organic phase was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The obtained solid was purified by column chromatography (n-hexane: dichloromethane = 10:1) to obtain a light 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 nitrogen atmosphere, intermediate product 1 (10 mmol, 3.54 g), furan-2-boric acid (12 mmol, 1.34 g,), tetrakistriphenylphosphine palladium (0.1 mmol, 116 mg) and potassium carbonate (20 mmol, 2.76 g) were added to a 100 mL round-bottom flask, and 50 mL toluene, 5 mL ethanol and 5 mL water were added, and refluxed at 85 ° C for 6 h. After the reaction was completed, the aqueous phase was extracted with toluene, and the obtained organic phase was dried over anhydrous sodium sulfate. After that, it was purified by vacuum rotary evaporation and column chromatography (n-hexane: dichloromethane = 15:1) to obtain a yellow solid, namely intermediate product 2 (2.73 g, yield 80%).

[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 nitrogen atmosphere, the intermediate product 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, and benzoyl chloride (2.4 mmol, 0.34 g) was added to the reaction system under ice-water bath conditions, and heated to reflux at 40°C for 6 hours. After the reaction was completed, the reaction solution was poured into 10 mL of 10% by volume ice-dilute hydrochloric acid aqueous solution (i.e., 0°C hydrochloric acid aqueous solution), extracted with dichloromethane three times, evaporated under reduced pressure, and finally purified by column chromatography (dichloromethane:n-hexane=1:2) to obtain a yellow-green solid, i.e., the intermediate product 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) The 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, a mixed solvent of petroleum ether and dichloromethane (petroleum ether: dichloromethane = 1:1) was used as an eluent for column chromatography separation and purification. The mixture was further recrystallized to obtain a white solid powder (0.82 g, yield 86%).

[0217] 1H NMR (500 MHz, CDCl3) δ 6.51 (t, J = 7.51 Hz, 1H), 6.88 (dd, J = 1.57, 7.38 Hz, 1H), 7.00 (tt, J = 1.98, 7.32 Hz, 1H), 7.21-7.28 (m, 3H), 7.37 (td, J = 2.01, 7.50 Hz, 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, 7.37 Hz, 1H), 8.69 (s, 1H). M / Z: Found, 478.3654; Calc, 477.1035.

[0218] Other compounds of the present application can be synthesized by selecting suitable raw materials according to the ideas of the above synthesis examples, or by selecting any other suitable methods and raw materials for synthesis.

[0219] Example 1

[0220] A glass substrate coated with a 150 nm thick ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone-ethanol mixed solvent, baked in a clean environment until the water was completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam to obtain a glass substrate with an anode;

[0221] Then, the glass substrate with the anode is placed in a vacuum chamber and evacuated to less than 10 -5 A hole injection layer is vacuum-deposited on the anode layer film of the glass substrate with an anode. The hole injection layer comprises a hole injection layer material HT-11 and a p-type dopant p-1. The hole injection layer is evaporated by a multi-source co-evaporation method. The evaporation rate of the hole injection layer material HT-11 is adjusted to 0.1 nm / s, the evaporation rate of the p-type dopant p-1 is 3% of the evaporation rate of the hole injection layer material HT-11, and the total evaporation film thickness is 10 nm. The hole injection layer material HT-11 and the p-type dopant p-1 are as follows:

[0222]

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

[0224]

[0225] Then, a light-emitting layer is vacuum-deposited on the hole transport layer. The light-emitting layer includes a light-emitting layer main material H3 and a light-emitting layer guest material BD-1. The light-emitting layer is evaporated by a multi-source co-evaporation method. The evaporation rate of the light-emitting layer main material H3 is adjusted to 0.1 nm / s, and the evaporation rate of the light-emitting layer guest material BD-1 is 3% of the evaporation rate of the light-emitting layer main material H3. The total evaporation film thickness is 30 nm. The light-emitting layer main material H3 and the light-emitting layer guest material BD-1 are as follows:

[0226]

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

[0228]

[0229] Then, LiF with a thickness of 10 nm was vacuum-deposited on the electron transport layer as an electron injection layer, wherein the evaporation rate was 0.1 nm / s;

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

[0231] Example 2-12

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

[0233] Comparative Example 1

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

[0235]

[0236] The organic electroluminescent device prepared by the above process was subjected to the following performance tests:

[0237] At the same brightness, the driving voltage, current efficiency and device life of the organic electroluminescent devices prepared in Examples 1-12 and Comparative Example 1 were measured using a digital source meter and a brightness meter. Specifically, the voltage was increased at a rate of 0.1 V per second, and the brightness of the organic electroluminescent device was measured when it reached 1000.00 cd / m 2The voltage at which the light is on is the driving voltage, and the current density at this time is measured at the same time; the ratio of brightness to current density is the current efficiency; the life test of LT95 is as follows: use a brightness meter at 1000cd / m 2 At the same brightness, the current is kept constant and the brightness of the organic electroluminescent device is measured to drop to 950cd / m 2 The time is in hours. The results are shown in Table 1.

[0238] Table 1 Performance results of organic electroluminescent devices

[0239]

[0240] As can be seen from Table 1, the compounds H3, H4, H8, H10, H15, H25, H36, H37, H38, H44, H45, and H52 prepared in the present application are used as the main material of the light-emitting layer in the organic electroluminescent device. Compared with Comparative Example 1, the driving voltage of the organic electroluminescent device is significantly lower, the current efficiency is significantly higher, and the LT95 life is significantly longer. The results show that the compounds provided in the present application are used as the main material of the light-emitting layer in the organic electroluminescent device, which can effectively reduce the driving voltage, improve the current efficiency, and extend the service life of the device, and are the main materials of the light-emitting layer with good performance.

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

Claims

1. A compound represented by formula (I): in, R 1 -R 5 are each independently selected from hydrogen, deuterium, C1-C6 alkyl, C1-C6 alkenyl which is unsubstituted or substituted by Ra, C6-C 30 Aryl, unsubstituted or substituted C3-C 30 Heteroaryl, R 1 and R 2 can be connected to form a ring, R 3 and R 5 Can be connected to form a ring; A is selected from C6-C 30 Aryl, unsubstituted or substituted C3-C 18 heteroaryl; B is selected from C3-C 10 Cycloalkyl, unsubstituted or substituted C6-C 30 Aryl, unsubstituted or substituted C3-C 18 heteroaryl; X 1 Selected from CR 6 or N, R 6 is selected from hydrogen, deuterium, C1-C6 alkyl, C6-C 30 Aryl, unsubstituted or substituted C3-C 18 Heteroaryl, R 6 and A can be connected to form a ring; X 2 Selected from CR 7 R 8 , O or SO2, R 7 and R 8 are each independently selected from hydrogen, deuterium, C1-C6 alkyl, C6-C6 unsubstituted or substituted by Ra 30 Aryl, unsubstituted or substituted C3-C 30 Heteroaryl, R 7 and R 8 Can be connected to form a ring; L is selected from a chemical bond, an unsubstituted or Ra-substituted C6-C 30 Arylene, unsubstituted or substituted C3-C 30 heteroarylene; The heteroatoms on the heteroaryl group or the heteroarylene group are each independently selected from N, O, and S; The Ra are each independently selected from deuterium, halogen, nitro, cyano, C1-C4 alkyl, phenyl, biphenyl, naphthyl, C1-C4 haloalkyl, quinoxalinyl, quinolyl, pyridyl or benzofuranyl.

2. The compound according to claim 1, wherein The compound is a compound represented by formula (II): in, R 3 -R 5 , R 9 -R 12 are each independently selected from hydrogen, deuterium, C1-C6 alkyl, C6-C6 unsubstituted or substituted by Ra 18 Aryl, unsubstituted or substituted C3-C 18 Heteroaryl, R 3 and R 5 Can be connected to form a ring; A is selected from C6-C 30 Aryl, unsubstituted or substituted C3-C 18 heteroaryl; B is selected from C3-C6 cycloalkyl, unsubstituted or substituted C6-C 18 Aryl, unsubstituted or substituted C3-C 18 heteroaryl; L is selected from a chemical bond, an unsubstituted or Ra-substituted C6-C 18 Arylene, unsubstituted or substituted C3-C 10 heteroarylene; The heteroatoms on the heteroaryl group or the heteroarylene group are each independently selected from N, O, and S; The Ra are each independently selected from deuterium, halogen, nitro, cyano, C1-C4 alkyl, phenyl, biphenyl, naphthyl, C1-C4 haloalkyl, quinoxalinyl, quinolyl, pyridyl or benzofuranyl.

3. The compound according to claim 2, wherein R 3 -R 5 , R 9 -R 12 each independently selected from hydrogen, deuterium, methyl, ethyl, propyl, a group of the following compounds which are unsubstituted or substituted with Ra: 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 can be connected to form a ring; and / or, A is selected from the group of the following compounds which 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; and / or, B is selected from the group consisting of cyclopropane, cyclobutane, cyclopentane, cyclohexane, 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; and / or, L is selected from a chemical bond, a subunit of the following compounds which is unsubstituted or substituted by Ra: benzene, biphenyl, naphthalene, phenanthrene, pyrene, fluorene, imidazole.

4. The compound according to claim 1, wherein The compound is selected from: 5 . A host material for a light-emitting layer, comprising at least one of the compounds according to claim 1 . 6 . An organic electroluminescent device comprising at least one of the light-emitting layer host materials according to claim 5 .

7. A display device comprising the organic electroluminescent device according to claim 6.

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