An organic electroluminescent device comprising a bisubstituted ortho-phenanthroline compound

Abstract

The application provides an organic electroluminescent device, which comprises a charge generation layer and an electron transport layer; the charge generation layer comprises a compound of formula (I), and the electron transport layer comprises a compound of formula (II). The organic electroluminescent device provided by the application has a parent structure of a double-substituted phenanthroline charge generation material, has high charge generation capacity, can effectively improve the luminous efficiency of the organic electroluminescent device, and can effectively improve the charge transport function of the organic electroluminescent device when used in combination with the electron transport material provided by the application, thereby improving the luminous efficiency of the organic electroluminescent device, reducing the driving voltage of the organic electroluminescent device and prolonging the service life of the organic electroluminescent device.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of organic light-emitting display, in particular to an organic electroluminescent device containing a bisubstituted phenanthroline compound. BACKGROUND

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

[0003] With the continuous advancement of OLED technology in the fields of lighting and display, people pay more attention to the research of high-efficiency organic materials that affect the performance of OLED devices. An OLED with good efficiency and long service life is usually the result of optimization of device structure and various organic materials, which provides great opportunities and challenges for chemists to design and develop functional materials with various structures. The stacked structure of an organic electroluminescent device can effectively improve the service life of the device, and thus has become a research hotspot in recent years. The development of high-efficiency charge generation materials and the selection of matching light-emitting units are the research focus. SUMMARY

[0004] The purpose of the present application is to provide an organic electroluminescent device, which can improve the working efficiency and prolong the service life of the organic electroluminescent device.

[0005] The first aspect of the present application provides an organic electroluminescent device comprising a charge generation layer and an electron transport layer.

[0006] The charge generation layer comprises a compound of formula (I):

[0007]

[0008] wherein,

[0009] L 1 and L 2 are each independently selected from a chemical bond, an unsubstituted or Rc-substituted C6-C 30 arylene group, an unsubstituted or Rc-substituted C3-C 30 heteroarylene group;

[0010] X1 -X 10 selected from CR or N, R is selected from hydrogen, deuterium, C1-C4 alkyl, C2-C6 alkenyl, amine, hydroxyl, C6-C10 aryl unsubstituted or substituted by Rc, C3-C10 heteroaryl unsubstituted or substituted by Rc, and adjacent R can be connected to form a ring, and X is selected from CR or N; 30 aryl unsubstituted or substituted by Rc, C3-C10 heteroaryl unsubstituted or substituted by Rc, and adjacent R can be connected to form a ring, and X is selected from CR or N; 30 heteroaryl unsubstituted or substituted by Rc, and adjacent R can be connected to form a ring, and X is selected from CR or N; 1 -X 10 at least one of which is N;

[0011] The electron transport layer comprises a compound of formula (II):

[0012]

[0013] wherein,

[0014] Ar 1 and Ar 2 each independently selected from C6-C10 aryl unsubstituted or substituted by Rc, C3-C10 heteroaryl unsubstituted or substituted by Rc, and at least one is selected from C6-C10 aryl unsubstituted or substituted by Rc; 30 aryl unsubstituted or substituted by Rc, C3-C10 heteroaryl unsubstituted or substituted by Rc, and at least one is selected from C6-C10 aryl unsubstituted or substituted by Rc; 30 heteroaryl unsubstituted or substituted by Rc, and at least one is selected from C6-C10 aryl unsubstituted or substituted by Rc; 30 aryl;

[0015] X 11 -X 13 each independently selected from CH or N, and at least two are selected from N;

[0016] R 1 and R 2 each independently selected from hydrogen, C6-C10 aryl unsubstituted or substituted by Rc, C3-C10 heteroaryl unsubstituted or substituted by Rc, and at least one is selected from C6-C10 aryl unsubstituted or substituted by Rc; 30 aryl unsubstituted or substituted by Rc, C3-C10 heteroaryl unsubstituted or substituted by Rc, and at least one is selected from C6-C10 aryl unsubstituted or substituted by Rc; 30 heteroaryl;

[0017] L is selected from a chemical bond, C6-C10 arylene unsubstituted or substituted by Rc, C3-C10 heteroarylene unsubstituted or substituted by Rc, and at least one is selected from C6-C10 arylene unsubstituted or substituted by Rc; 30 arylene unsubstituted or substituted by Rc, C3-C10 heteroarylene unsubstituted or substituted by Rc, and at least one is selected from C6-C10 arylene unsubstituted or substituted by Rc; 30 heteroarylene;

[0018] each of the heteroatoms on the heteroaryl or the heteroarylene is independently selected from O, S or N;

[0019] each substituent Rc of the respective group is independently selected from deuterium, halogen, nitro, cyano, C1-C4 alkyl, phenyl, biphenyl, terphenyl, pyrimidinyl or naphthyl.

[0020] The second aspect of the present application provides a display device comprising the organic electroluminescent device provided by the first aspect of the present application.

[0021] The beneficial effects of the present application are:

[0022] The organic electroluminescent device provided by the present application has a charge generation material with a parent structure of a double-substituted phenanthroline, high charge generation capability, and can effectively improve the luminous efficiency of the organic electroluminescent device. Meanwhile, the charge generation material is used in combination with the electron transport material provided by the present application, which can effectively improve the charge transport function of the organic electroluminescent device, improve the luminous efficiency of the organic electroluminescent device, reduce the driving voltage of the organic electroluminescent device, and prolong the service life of the organic electroluminescent device. In addition, the charge generation material and the electron transport material used in combination by the present application have the characteristics of high bond energy between atoms, large conjugated plane, good thermal stability, and favorable solid-state accumulation between molecules, which can achieve good luminous efficiency in the organic electroluminescent device, reduce the driving voltage of the organic electroluminescent device, and prolong the service life of the organic electroluminescent device. The display device provided by the present application has excellent display effect.

[0023] Of course, implementing any product or method of the present application does not necessarily require all the advantages described above. BRIEF DESCRIPTION OF DRAWINGS

[0024] In order to more clearly illustrate the technical solutions of the embodiments of the present application, the drawings needed in the embodiment description will be briefly introduced below. Obviously, the drawings in the following description are only some embodiments of the present application, and other embodiments can also be obtained by those skilled in the art based on these drawings.

[0025] Figure 1 The organic electroluminescent device of one embodiment of the present application is shown in the schematic diagram. DETAILED DESCRIPTION

[0026] The technical solutions in the embodiments of the present application will be described clearly and completely below with reference to the drawings in the embodiments of the present application. Obviously, the described embodiments are only some embodiments of the present application, not all embodiments. All other embodiments obtained by those skilled in the art based on the present application are within the scope of protection of the present application.

[0027] The first aspect of the present application provides an organic electroluminescent device comprising a charge generation layer and an electron transport layer;

[0028] The charge generation layer comprises a compound of formula (I):

[0029]

[0030] wherein,

[0031] L 1 and L 2 each independently is selected from a chemical bond, C6-C30 arylene, C3-C 30 heteroarylene;

[0032] X 1 -X 10 selected from CR or N, R is selected from hydrogen, deuterium, C1-C4alkyl, C2-C6alkenyl, amine, hydroxyl, C6-C 30 aryl, C3-C 30 heteroaryl, and adjacent R can be linked to form a ring, and X 1 -X 10 at least one of which is N;

[0033] The electron transport material comprises a compound of formula (II):

[0034]

[0035] wherein,

[0036] Ar 1 and Ar 2 are each independently selected from C6-C 30 aryl, C3-C 30 heteroaryl, and at least one is selected from C6-C 30 aryl;

[0037] X 11 -X 13 are each independently selected from CH or N, and at least two are selected from N;

[0038] R 1 and R 2 are each independently selected from hydrogen, C6-C 30 aryl, C3-C 30 heteroaryl;

[0039] L is selected from a bond, C6-C 30 arylene, C3-C 30 heteroarylene;

[0040] the heteroatoms on the heteroaryl or the heteroarylene are each independently selected from O, S or N;

[0041] the substituents Rcfor each group are each independently selected from deuterium, halogen, nitro, cyano, C1-C4alkyl, phenyl, biphenyl, terphenyl, pyrimidinyl or naphthyl.

[0042] Preferably, the L1 and L 2 each independently selected from the group consisting of a bond, an unsubstituted or Rc-substituted group of the following compounds: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, anthracene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, quinazoline, quinoxaline, cinnoline, naphthridine, triazine, phenanthrolin, benzophenanthroline, pyridopyrazine, furan, benzofuran, dibenzofuran, aza-dibenzofuran, benzothiophene, dibenzothiophene, aza-dibenzothiophene, 9,9-dimethylfluorene, spirofluorene.

[0043] Preferably, said X 1 -X 10 selected from the group consisting of CR or N, R selected from the group consisting of hydrogen, deuterium, C1-C4 alkyl, C2-C6 alkenyl,..., a hydroxyl group, an unsubstituted or Rc-substituted group of the following compounds: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, anthracene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, quinazoline, quinoxaline, cinnoline, naphthridine, triazine, phenanthrolin, benzophenanthroline, pyridopyrazine, furan, benzofuran, dibenzofuran, aza-dibenzofuran, benzothiophene, dibenzothiophene, aza-dibenzothiophene, 9,9-dimethylfluorene, spirofluorene, phenylphosphinyl.

[0044] Preferably, said Ar 1 and Ar 2 each independently selected from the group consisting of an unsubstituted or Rc-substituted group of the following compounds: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, anthracene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, quinazoline, quinoxaline, cinnoline, naphthridine, triazine, phenanthrolin, benzophenanthroline, pyridopyrazine, furan, benzofuran, dibenzofuran, aza-dibenzofuran, benzothiophene, dibenzothiophene, aza-dibenzothiophene, 9,9-dimethylfluorene, spirofluorene, oxaspirofluorene, benzofluorene.

[0045] Preferably, said R 1 and R 2 each independently selected from the group consisting of hydrogen, an unsubstituted or Rc-substituted group of the following compounds: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, anthracene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, quinazoline, quinoxaline, cinnoline, naphthridine, triazine, phenanthrolin, benzophenanthroline, pyridopyrazine, furan, benzofuran, dibenzofuran, aza-dibenzofuran, benzothiophene, dibenzothiophene, aza-dibenzothiophene, 9,9-dimethylfluorene, spirofluorene.

[0046] Preferably, L is selected from the group consisting of a chemical bond, a radical of the following compounds which is unsubstituted or substituted by Rc: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, anthracene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, quinazoline, quinoxaline, cinnoline, naphthylidine, triazine, phenanthrolin, benzophenanthrolinyl, pyridopyrazine, furan, benzofuran, dibenzofuran, aza-dibenzofuran, benzothiophene, dibenzothiophene, aza-dibenzothiophene, 9,9-dimethylfluorene, spirofluorene.

[0047] In one embodiment of the present application, the compound of formula (I) is used in combination with a metal-containing material, the content of the metal-containing material being 0.5%-2.5% of the content of the charge generation layer; the metal-containing material is selected from at least one of a metal and a metal complex; the metal is selected from at least one of lithium (Li) and ytterbium (Yb), and the metal complex is selected from at least one of lithium 8-hydroxyquinolate (LiQ) and aluminum 8-hydroxyquinolate (AlQ3).

[0048] In one embodiment of the present application, the thickness of the charge generation layer is 10 nm-30 nm.

[0049] In one embodiment of the present application, the thickness of the electron transport layer is 10 nm-40 nm.

[0050] In one embodiment of the present application, the compound of formula (II) is used in combination with LiQ, the content of LiQ being 10%-90% of the content of the electron transport layer.

[0051] In one embodiment of the present application, the compound of formula (I) is selected from the group consisting of the compounds shown in A1-A30:

[0052]

[0053]

[0054] In one embodiment of the present application, the compound of formula (II) is selected from the group consisting of the compounds shown in B1-B22:

[0055]

[0056] The organic electroluminescent device provided by the present application comprises at least one of the charge generating materials provided by the present application and at least one of the electron transport materials. The charge generating materials provided by the present application have high charge generation capacity, and when used in combination with the electron transport materials provided by the present application, the charge transport function of the organic electroluminescent device can be effectively improved, the luminous efficiency of the organic electroluminescent device is improved, the driving voltage of the organic electroluminescent device is reduced, and the service life of the organic electroluminescent device is prolonged. In addition, the charge generating materials and the electron transport materials used in combination by the present application have the characteristics of high interatomic bond energy, large conjugated plane, good thermal stability, and favorable solid-state accumulation between molecules, which can achieve good luminous efficiency, reduce the driving voltage of the organic electroluminescent device, and prolong the service life of the organic electroluminescent device. Therefore, the organic electroluminescent device provided by the present application has low driving voltage, high luminous efficiency, and long service life.

[0057] In the present application, the type and structure of the organic electroluminescent device are not particularly limited, and can be different types and structures of organic electroluminescent devices known in the art, as long as at least one of the charge generating materials and at least one of the electron transport materials provided by the present application can be used.

[0058] In an embodiment of the present application, the organic electroluminescent device comprises an anode and a cathode, a number of m light-emitting units and a number of m-1 charge generating layers are stacked between the anode and the cathode, the charge generating layers are between two adjacent light-emitting units, and each of the charge generating layers comprises an n-type charge generating layer and a p-type charge generating layer, wherein m is an integer ≥ 2; each of the light-emitting units comprises at least one light-emitting layer, and the maximum emission wavelength of the light emitted by different light-emitting units is different; at least one of the n-type charge generating layers comprises at least one compound represented by formula (I) and a metal-containing material, the metal-containing material comprises a metal, a metal complex, or a combination thereof, at least one of the light-emitting units further comprises an electron transport layer on the cathode side of the light-emitting unit, and the electron transport layer comprises at least one compound represented by formula (II).

[0059] In an embodiment of the present application, the light-emitting unit in the organic electroluminescent device can comprise a first light-emitting unit and a second light-emitting unit, and the two light-emitting units can be the same or different; the charge generating layer can be arranged between the first light-emitting unit and the second light-emitting unit, the first light-emitting unit can be arranged between the anode and the charge generating layer, and the second light-emitting unit can be arranged between the charge generating layer and the cathode; the n-type charge generating layer of the charge generating layer can comprise at least one compound represented by formula (I) and a metal-containing material, and the second light-emitting unit can further comprise an electron transport layer between the light-emitting layer of the second light-emitting unit and the cathode, and the electron transport layer comprised in the second light-emitting unit can comprise at least one compound represented by formula (II).

[0060] In one embodiment of the present application, in an organic electroluminescent device having light-emitting units of 2, the first light-emitting unit can further include an HT-light-emitting auxiliary layer between the light-emitting layer of the first light-emitting unit and the anode, and the electron transport layer included in the first light-emitting unit can include at least one compound represented by formula (II). The at least one compound represented by formula (II) included in the electron transport layer of the first light-emitting unit can be the same as or different from the at least one compound represented by formula (II) included in the electron transport layer of the second light-emitting unit.

[0061] In one embodiment of the present application, the organic electroluminescent device of the present application can be a light-emitting device of a top emission structure, which can be exemplified by sequentially including an anode, a first light-emitting unit, a charge generation layer, a second light-emitting unit, an electron injection layer, and a transparent or semi-transparent cathode on a substrate.

[0062] The organic electroluminescent device of the present application can also be a light-emitting device of a bottom emission structure, which can be exemplified by sequentially including a transparent or semi-transparent anode, a first light-emitting unit, a charge generation layer, a second light-emitting unit, an electron injection layer, and a cathode structure on a substrate.

[0063] The organic electroluminescent device of the present application can also be a light-emitting device of a double-sided emission structure, which can be exemplified by sequentially including a transparent or semi-transparent anode, a first light-emitting unit, a charge generation layer, a second hole injection layer, a second light-emitting unit, an electron injection layer, and a transparent or semi-transparent cathode structure on a substrate.

[0064] The first light-emitting unit includes a first hole injection layer, a first hole transport layer, a first light-emitting layer, and a first electron transport layer disposed in this order, and the second light-emitting unit includes a second hole injection layer, a second hole transport layer, a second light-emitting layer, and a second electron transport layer disposed in this order.

[0065] Further, the organic electroluminescent device of the present application can have an electron blocking layer between the hole transport layer and the light-emitting layer, a hole blocking layer between the light-emitting layer and the electron transport layer, and a light extraction layer on the transparent electrode on the light-emitting side. However, the structure of the organic electroluminescent device of the present application is not limited to the above-described specific structure, and the above-described layers can be omitted or added as necessary. The thickness of each layer of the organic electroluminescent device is not particularly limited in the present application, as long as the object of the present application can be achieved. For example, the organic electroluminescent device can sequentially include an anode (100 nm to 150 nm) made of a metal, a first hole injection layer (5 nm to 20 nm), a first hole transport layer (80 nm to 140 nm), an electron blocking layer (5 nm to 20 nm), a first light-emitting layer (15 nm to 40 nm), a hole blocking layer (5 nm to 20 nm), a first electron transport layer (10 nm to 40 nm), a charge generation layer (10 nm to 30 nm), a second hole injection layer (5 nm to 20 nm), a second hole transport layer (80 nm to 140 nm), a second light-emitting layer (15 nm to 40 nm), a second electron transport layer (10 nm to 40 nm), an electron injection layer (5 nm to 20 nm), a transparent or semi-transparent cathode (100 nm to 160 nm), and a light extraction layer (50 nm to 90 nm) on a substrate. Illustratively, Figure 1 A schematic diagram of a typical organic electroluminescent device is shown, in which a substrate 21, a reflective anode 22, a first hole injection layer 23a, a first hole transport layer 24a, a first light-emitting layer 25a, a first electron transport layer 26a, a charge generation layer 29, a second hole injection layer 23b, a second hole transport layer 24b, a second light-emitting layer 25b, a second electron transport layer 26b, an electron injection layer 27, and a cathode electrode 28 are sequentially provided from the bottom to the top.

[0066] It is to be understood that Figure 1 The structure of a typical organic electroluminescent device is shown only schematically, and the present application is not limited to this structure. The charge generation material and the electron transport material of the present application can be used in any type of organic electroluminescent device.

[0067] For convenience, the organic electroluminescent device of the present application is described below, but this does not mean any limitation on the scope of protection of the present application. It is to be understood that all organic electroluminescent devices that can use the charge generation material and the electron transport material of the present application are within the scope of protection of the present application.

[0068] In the present application, the substrate 21 is not particularly limited, and a conventional substrate used in the organic electroluminescent device of the prior art, for example, glass, a polymeric material, and glass and polymeric materials with a thin film transistor (TFT) element, etc. can be used.

[0069] In the present application, the material of the reflective anode 22 is not particularly limited and can be selected from transparent conductive materials known in the art, such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), and the like, can be selected from metal materials, such as silver and alloys thereof, aluminum and alloys thereof, and the like, or can be selected from organic conductive materials, such as poly 3,4-ethylenedioxythiophene (PEDOT), or the reflective anode 22 is a multilayer structure formed of the above-mentioned materials, and the number of layers of the multilayer structure is not particularly limited and can be selected as needed, as long as the purpose of the present application is achieved, for example, 1 layer, 2 layers, 3 layers, or more.

[0070] In the present application, the material of the first hole injection layer 23a and the second hole injection layer 23b is not particularly limited and can be made of a hole injection layer material known in the art or a hole transport material (HTM) known in the art. For example, at least one of the known HTMs is selected as a hole injection material.

[0071] In the present application, the first hole injection layer 23a and the second hole injection layer 23b can each include a p-type dopant, and the type of the p-type dopant is not particularly limited and can be various p-type dopants known in the art. For example, the p-type dopant can be selected from, but is not limited to, at least one of the following p-1 to p-3 compounds:

[0072]

[0073] In the present application, the amount of the p-type dopant is not particularly limited and can be an amount known to those skilled in the art.

[0074] In the present application, the material of the first hole transport layer 24a and the second hole transport layer 24b is not particularly limited and can be made of an HTM known in the art. The number of layers of the first hole transport layer 24a and the second hole transport layer 24b is not particularly limited and can be adjusted as needed, as long as the purpose of the present application is achieved, for example, 1 layer, 2 layers, 3 layers, 4 layers, or more.

[0075] For example, the HTM for the hole injection layer material and the HTM for the hole transport layer material can be selected from, but is not limited to, at least one of the following HT-1 to HT-31 compounds:

[0076]

[0077]

[0078] In the present application, the materials of the first light-emitting layer 25a and the second light-emitting layer 25b are not particularly limited, and each can include a light-emitting layer host material and a light-emitting layer guest material, wherein the amount of the light-emitting layer host material and the light-emitting layer guest material is not particularly limited, and can be an amount known to those skilled in the art.

[0079] In the present application, the host material of the first light-emitting layer 25a and the second light-emitting layer 25b is not particularly limited, and at least one of the red light-emitting layer host materials known in the art can be used. For example, it can be selected from, but not limited to, at least one of the following RH-1 to RH-13 compounds:

[0080]

[0081]

[0082] The light-emitting layer host material can also use at least one of the green light-emitting layer host materials known in the art. For example, it can be selected from, but not limited to, at least one of the following GPH-1 to GPH-80 compounds:

[0083]

[0084]

[0085]

[0086]

[0087]

[0088] The light-emitting layer host material can also use at least one of the blue light-emitting layer host materials known in the art. For example, it can be selected from, but not limited to, at least one of the following BH-1 to BH-10 compounds:

[0089]

[0090] In the present application, the guest material of the first light-emitting layer 25a and the second light-emitting layer 25b is not particularly limited, and at least one of the red light-emitting layer guest materials known in the art can be used. For example, it can be selected from, but not limited to, at least one of the following RPD-1 to RPD-28 compounds:

[0091]

[0092]

[0093] The light-emitting layer guest material can be a green light-emitting layer guest material, for example, it can be selected from, but not limited to, at least one of the following GD01 to GD04 compounds:

[0094]

[0095] The light-emitting layer guest material can be a blue light-emitting layer guest material, 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:

[0096]

[0097] In the present application, the amount of the light-emitting layer guest material is not particularly limited and can be an amount known to those skilled in the art.

[0098] In the present application, the first electron transport layer 26a and the second electron transport layer 26b contain at least one of the electron transport materials of the present application, and can also contain a combination of at least one of the electron transport materials of the present application and at least one of known electron transport materials. The number of layers of the first electron transport layer 26a and the second electron transport layer 26b is not particularly limited and can be adjusted as needed, as long as the purpose of the present application is met, for example, 1 layer, 2 layers, 3 layers, 4 layers or more.

[0099] For example, the known electron transport material can be selected from, but not limited to, at least one of the following ET-1 to ET-57 compounds:

[0100]

[0101]

[0102]

[0103]

[0104] In the present application, the first electron transport layer 26a and the second electron transport layer 26b can each further include an n-type dopant, and the type of the n-type dopant is not particularly limited and various n-type dopants known in the art can be used, for example, the following n-type dopants can be used:

[0105]

[0106] 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.

[0107] In the present application, the charge generation layer 29 can contain at least one of the charge generation materials of the present application, and can also contain a combination of at least one of the charge generation materials of the present application and at least one of the following known charge generation materials.

[0108] For example, the known charge generation material can be selected from, but not limited to, at least one of the following CGL00R1 to CGL00R4 compounds:

[0109]

[0110] In the present application, the charge generation layer can further include at least one of the following metals: Li, Yb.

[0111] In the present application, the material of the electron injection layer 27 is not particularly limited, and known electron injection materials in the art can be used, for example, can include, but are 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.

[0112] In the present application, the material of the cathode electrode 28 is not particularly limited, and can be selected from, but not limited to, magnesium silver mixture, LiF / Al, ITO, Al, etc. metals, metal mixtures, oxides, etc.

[0113] The method for preparing the organic electroluminescent device of the present application is not particularly limited, and any method known in the art can be used, for example, the present application can be prepared by the following preparation method:

[0114] The method for preparing the organic electroluminescent device of the present application can further include, but is not limited to, the following steps:

[0115] (1) cleaning the reflective anode 22 on the top-emitting organic electroluminescent device substrate 21, respectively through the steps of pickling, washing, brushing, high-pressure washing, air knife, etc. in a cleaning machine, and then heating treatment;

[0116] (2) vacuum evaporation of a hole injection material as a first hole injection layer 23a on the reflective anode 22;

[0117] (3) vacuum evaporation of a hole transport material as a first hole transport layer 24a on the first hole injection layer 23a;

[0118] (4) vacuum evaporation of a first light-emitting layer 25a containing a host material and a guest material on the first hole transport layer 24a;

[0119] (5) vacuum evaporation of an electron transport material as a first electron transport layer 26a on the first light-emitting layer 25a;

[0120] (6) vacuum evaporation of a charge generation material as a charge generation layer 29 on the first electron transport layer 26a;

[0121] (7) vacuum evaporation of a hole injection material as a second hole injection layer 23b on the charge generation layer 29;

[0122] (8) vacuum deposition of a hole transport material as a second hole transport layer 24b on the second hole injection layer 23b;

[0123] (9) vacuum deposition of a second light emitting layer 25b containing a host material and a guest material on the second hole transport layer 24b;

[0124] (10) vacuum deposition of an electron transport material as a second electron transport layer 26b on the second light emitting layer 25b;

[0125] (11) vacuum deposition of an electron injection material as an electron injection layer 27 on the second electron transport layer 26b;

[0126] (12) vacuum deposition of a cathode material as a cathode electrode 28 on the electron injection layer 27.

[0127] The above only describes one typical structure of an organic electroluminescent device and a method for preparing the same, and it should be understood that the present application is not limited to this structure. The electron transport material of the present application can be used in an organic electroluminescent device of any structure, and the organic electroluminescent device can be prepared by any method known in the art.

[0128] A second aspect of the present application provides a display device comprising the organic electroluminescent device provided by the first aspect of the present application. The display device includes, but is not limited to, a display, a television, a tablet computer, a mobile communication terminal, and the like.

[0129] 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 illustrates the synthesis process of the compound of the present application.

[0130] Synthesis Example

[0131] Synthesis of Compound A1

[0132]

[0133] In a reaction bottle, 100 mmol of 2-bromo-5-chloropyridine, 100 mmol of phenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of tetrahydrofuran (THF) and 200 mL of water were added, and 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) was added, and reacted at 60°C for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M1. The amount of Pd(PPh3)4 added was 1 mol% of 2-bromo-5-chloropyridine.

[0134] In a reaction flask, 100 mmol of Ml, 100 mmol of p-chlorophenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF and 200 mL of water were added, and 1 mol% of Pd(PPh3)4was added, and reacted at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M2. At this time, the amount of Pd(PPh3)4added was 1 mol% of Ml.

[0135] In a reaction flask, 100 mmol of M2, 100 mmol of pinacol diboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane, and 1 mol% of Pd(PPh3)4were added, and reacted at 100°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M3. At this time, the amount of Pd(PPh3)4added was 1 mol% of M2.

[0136] In a reaction flask, 100 mmol of 2,9-dichloro-1,10-phenanthroline, 200 mmol of M3, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF and 200 mL of water were added, and 2 mol% of Pd(PPh3)4was added, and reacted at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder A1. At this time, the amount of Pd(PPh3)4added was 2 mol% of 2,9-dichloro-1,10-phenanthroline.

[0137] 1 H NMR (400 MHz, Chloroform) 8.93 (s, 2H), 8.69 (s, 4H), 8.36 (d, J = 10.0 Hz, 6H), 8.01 (s, 2H), 7.93 (s, 2H), 7.73 (s, 2H), 7.52 (d, J = 10.0 Hz, 6H), 7.29 (d, J = 8.8.0 Hz, 6H).

[0138] Synthesis of Compound A4:

[0139]

[0140] In a reaction flask, 100 mmol of p-bromoiodobenzene, 100 mmol of pyridine-3-boronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and the reaction was performed at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M1. Herein, the amount of Pd(PPh3)4 added was 1 mol% of p-bromoiodobenzene.

[0141] In a reaction flask, 100 mmol of M1, 100 mmol of pinacol diboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane, and 1 mol% of Pd(PPh3)4 were added, and the reaction was performed at 100°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M2. Herein, the amount of Pd(PPh3)4 added was 1 mol% of M1.

[0142] In a reaction flask, 100 mmol of M2, 100 mmol of 2,9-dichloro-1,10-phenanthroline, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and the reaction was performed at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M3. Herein, the amount of Pd(PPh3)4 added was 1 mol% of M2.

[0143] In a reaction flask, 100 mmol of 9-bromophenanthrene, 100 mmol of p-chlorophenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and the reaction was performed at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M4. Herein, the amount of Pd(PPh3)4 added was 1 mol% of 9-bromophenanthrene.

[0144] In a reaction flask, 100 mmol of M4, 100 mmol of pinacol diboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane, and 1 mol% of Pd(PPh3)4 were added, and the reaction was performed at 100°C for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M5. Herein, the amount of Pd(PPh3)4 added was 1 mol% of M4.

[0145] In a reaction flask, 100 mmol of M3, 100 mmol of M5, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added, and 2 mol% of Pd(PPh3)4 was added, and the reaction was performed at 60°C for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder A4. Herein, the amount of Pd(PPh3)4 added was 2 mol% of M3.

[0146] 1 H NMR (400 MHz, Chloroform) 9.22 (s, 1H), 9.01 (s, 1H), 8.98-8.72 (m, 4H), 8.49-8.25 (m, 3H), 7.89 (d, J=10.0 Hz, 2H), 7.69 (d, J=10.0 Hz, 2H), 7.56-7.41 (m, 8H), 7.30 (d, J=10.0 Hz, 6H).

[0147] Synthesis of compound A5:

[0148]

[0149] In a reaction flask, 100 mmol of 2-iodo-5-bromopyrimidine, 100 mmol of 9-phenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and the reaction was performed at 60°C for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M1. Herein, the amount of Pd(PPh3)4 added was 1 mol% of 2-iodo-5-bromopyrimidine.

[0150] In a reaction flask, 100 mmol of Ml, 100 mmol of bis(pinacolato)diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane, and 1 mol% of Pd(PPh3)4 were added, and reacted at 100°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M2. At this time, the amount of Pd(PPh3)4 added was 1 mol% of Ml.

[0151] In a reaction flask, 100 mmol of 4-biphenylboronic acid, 100 mmol of 2,9-dichloro-1,10-phenanthroline, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and reacted at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M3. At this time, the amount of Pd(PPh3)4 added was 1 mol% of M2.

[0152] In a reaction flask, 100 mmol of M2, 100 mmol of M3, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added, and 2 mol% of Pd(PPh3)4 was added, and reacted at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder A5. At this time, the amount of Pd(PPh3)4 added was 2 mol% of M2.

[0153] 1 H NMR (400 MHz, Chloroform) 9.65 (s, 1H), 9.08 (s, 1H), 8.76 (d, J = 8.0 Hz, 2H), 8.69 - 8.56 (m, 4H), 8.39 (s, 1H), 8.34 - 8.01 (m, 5H), 7.84 (d, J = 10.0 Hz, 2H), 7.78 (d, J = 8.0 Hz, 2H), 7.68 (d, J = 7.6 Hz, 2H), 7.63 - 7.43 (m, 6H).

[0154] Synthesis of Compound A7:

[0155]

[0156] In a reaction flask, 100 mmol of 2-bromo-5-chloropyridine, 100 mmol of phenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and the reaction was performed at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M1. At this time, the amount of Pd(PPh3)4 added was 1 mol% of 2-bromo-5-chloropyridine.

[0157] In a reaction flask, 100 mmol of M1, 100 mmol of p-chlorophenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and the reaction was performed at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M2. At this time, the amount of Pd(PPh3)4 added was 1 mol% of M1.

[0158] In a reaction flask, 100 mmol of M2, 100 mmol of pinacol diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane, and 1 mol% of Pd(PPh3)4 were added, and the reaction was performed at 100°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M3. At this time, the amount of Pd(PPh3)4 added was 1 mol% of M2.

[0159] In a reaction flask, 100 mmol of 2,9-dichloro-1,10-phenanthroline, 100 mmol of M3, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added, and 2 mol% of Pd(PPh3)4 was added, and the reaction was performed at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M4. At this time, the amount of Pd(PPh3)4 added was 2 mol% of 2,9-dichloro-1,10-phenanthroline.

[0160] In a reaction flask, 100 mmol of 2-bromoquinoline, 100 mmol of p-chlorophenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added, and 1 mol% of Pd(PPh3)4was added, and the reaction was performed at 60°C for 12 h. After the completion of the reaction, the reaction was stopped, and the reaction material was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M5. Herein, the amount of Pd(PPh3)4to be added was 1 mol% of 2-bromoquinoline.

[0161] In a reaction flask, 100 mmol of M5, 100 mmol of pinacol diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane, and 1 mol% of Pd(PPh3)4were added, and the reaction was performed at 100°C for 12 h. After the completion of the reaction, the reaction was stopped, and the reaction material was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M6. Herein, the amount of Pd(PPh3)4to be added was 1 mol% of M5.

[0162] In a reaction flask, 100 mmol of M4, 100 mmol of M6, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added, and 1 mol% of Pd(PPh3)4was added, and the reaction was performed at 60°C for 12 h. After the completion of the reaction, the reaction was stopped, and the reaction material was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder A7. Herein, the amount of Pd(PPh3)4to be added was 1 mol% of M4.

[0163] 1 H NMR (400 MHz, Chloroform) 9.26 (s, 1H), 8.69 (s, 1H), 8.38 (d, J = 10.4 Hz, 6H), 8.10 (s, 1H), 7.89 (d, J = 11.2 Hz, 4H), 7.82 - 7.64 (m, 4H), 7.56 (d, J = 10.0 Hz, 4H), 7.42 (d, J = 10.0 Hz, 6H).

[0164] Synthesis of Compound A10:

[0165]

[0166] 100 mmol of 2-bromo-5-chloropyridine, 100 mmol of phenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added to a reaction flask, and 1 mol% of Pd(PPh3)4 was added. The reaction was allowed to proceed at 60°C for 12 hours. After completion of the reaction, the reaction was stopped, and the reactants were cooled to room temperature, added with water, filtered, and washed with water. The resulting solid was recrystallized and purified from toluene to obtain a white powder M1. The amount of Pd(PPh3)4 added was 1 mol% of the 2-bromo-5-chloropyridine.

[0167] 100 mmol of M1, 100 mmol of p-chlorophenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added to a reaction flask. 1 mol% of Pd(PPh3)4 was also added, and the reaction was continued at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reactants were cooled to room temperature, added with water, filtered, and washed with water. The resulting solid was recrystallized and purified from toluene to obtain a white powder M2. The amount of Pd(PPh3)4 added was 1 mol% of M1.

[0168] To a reaction flask, 100 mmol of M2, 100 mmol of pinacol diboronate, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane, and 1 mol% of Pd(PPh3)4 were added, and the mixture was reacted at 100°C for 12 hours. After completion, the reaction was stopped, and the reactants were cooled to room temperature, added with water, filtered, and washed with water. The resulting solid was recrystallized and purified from toluene to obtain a white powder, M3. The amount of Pd(PPh3)4 added was 1 mol% of M2.

[0169] To a reaction flask, 100 mmol of 2,9-dichloro-1,10-phenanthroline, 100 mmol of M3, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added. 2 mol% of Pd(PPh3)4 was then added and the mixture was allowed to react at 60°C for 12 hours. After completion, the reaction was stopped and the product was cooled to room temperature, water was added, filtered, and washed. The resulting solid was recrystallized and purified from toluene to obtain a white powder, M4. The amount of Pd(PPh3)4 added was 2 mol% of the 2,9-dichloro-1,10-phenanthroline.

[0170] In a reaction flask, 100 mmol of M4, 100 mmol of 9,9'-spirobifluorene-2-boronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and reacted at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder A10. Herein, the amount of Pd(PPh3)4 added was 1 mol% of M4.

[0171] 1 H NMR (400 MHz, Chloroform) 9.26 (s, 1H), 8.69 (s, 1H), 8.38 (d, J = 10.0 Hz, 4H), 8.09 (s, 1H), 7.92-7.80 (m, 6H), 7.64 (s, 1H), 7.51 (d, J = 8.4 Hz, 6H), 7.34 (d, J = 8.4 Hz, 6H), 7.24 (t, J = 8.0 Hz, 6H).

[0172] Synthesis of compound A15:

[0173]

[0174] In a reaction flask, 100 mmol of 2,3-dichloroquinoxaline, 100 mmol of phenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and reacted at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M1. Herein, the amount of Pd(PPh3)4 added was 1 mol% of 2,3-dichloroquinoxaline.

[0175] In a reaction flask, 100 mmol of M1, 100 mmol of p-chlorophenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and reacted at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M2. Herein, the amount of Pd(PPh3)4 added was 1 mol% of M1.

[0176] In a reaction flask, 100 mmol of M2, 100 mmol of bis(pinacolato)diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane, and 1 mol% of Pd(PPh3)4 were added, and the reaction was performed at 100°C for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M3. Herein, the amount of Pd(PPh3)4 added was 1 mol% of M2.

[0177] In a reaction flask, 100 mmol of 4-biphenylboronic acid, 100 mmol of 2,9-dichloro-1,10-phenanthroline, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and the reaction was performed at 60°C for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M4. Herein, the amount of Pd(PPh3)4 added was 1 mol% of 2,9-dichloro-1,10-phenanthroline.

[0178] In a reaction flask, 100 mmol of M3, 100 mmol of M4, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added, and 2 mol% of Pd(PPh3)4 was added, and the reaction was performed at 60°C for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder A15. Herein, the amount of Pd(PPh3)4 added was 2 mol% of M3.

[0179] 1 H NMR (400 MHz, Chloroform) 8.89-8.55 (m, 4H), 8.39 (s, 1H), 8.03-7.83 (m, 5H), 7.80 (s, 1H), 7.67 (s, 1H), 7.59 (d, J = 8.0 Hz, 4H), 7.52-7.41 (m, 6H), 7.33 (d, J = 10.0 Hz, 6H).

[0180] Synthesis of compound A23:

[0181]

[0182] In a reaction flask, 100 mmol of 4-iodo-4-bromobiphenyl, 100 mmol of pyridine-3-boronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and reacted at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M1. At this time, the amount of Pd(PPh3)4 added was 1 mol% of 4-iodo-4-bromobiphenyl.

[0183] In a reaction flask, 100 mmol of M1, 100 mmol of pinacol diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane were added, and 1 mol% of Pd(PPh3)4 was added, and reacted at 100°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M2. At this time, the amount of Pd(PPh3)4 added was 1 mol% of M1.

[0184] In a reaction flask, 100 mmol of M2, 100 mmol of 2,9-dichloro-1,10-phenanthroline, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and reacted at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M3. At this time, the amount of Pd(PPh3)4 added was 1 mol% of M2.

[0185] In a reaction flask, 100 mmol of (4-bromophenyl)diphenylphosphine oxide, 100 mmol of p-chlorophenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and reacted at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M4. At this time, the amount of Pd(PPh3)4 added was 1 mol% of (4-bromophenyl)diphenylphosphine oxide.

[0186] To a reaction flask, 100 mmol of M4, 100 mmol of pinacol diboronate, 41.4 g of potassium carbonate (300 mmol), and 800 mL of dioxane were added, along with 1 mol% of Pd(PPh3)4. The mixture was reacted at 100°C for 12 h. After completion, the reaction was stopped and the product was cooled to room temperature, water was added, filtered, and washed. The resulting solid was recrystallized from toluene to obtain a white powder, M5. The amount of Pd(PPh3)4 added was 1 mol% of M4.

[0187] To a reaction flask were added 100 mmol of M3, 100 mmol of M5, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water. 2 mol% of Pd(PPh3)4 was also added, and the mixture was reacted at 60°C for 12 h. After completion of the reaction, the reaction was stopped, and the reactants were cooled to room temperature, added with water, filtered, and washed with water. The resulting solid was recrystallized and purified from toluene to obtain a white powder A23. The amount of Pd(PPh3)4 added was 2 mol% of M3.

[0188] 1 H NMR(400MHz,Chloroform)9.24(s,1H),8.70(d,J=8.0Hz,6H),8.36(d,J=10.0Hz,4H),7.97(s,1H),7.8 5(s,1H),7.82(d,J=10.0Hz,4H),7.58(s,1H),7.55(d,J=12.0Hz,6H),7.47-7.32(m,11H),7.25(s,1H).

[0189] Synthesis of compound B2

[0190]

[0191] To a reaction flask, 100 mmol of 2-naphthaleneboronic acid, 100 mmol of 2,7-dibromonaphthalene, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added. 1 mol% of Pd(PPh3)4 was also added, and the mixture was reacted at 60°C for 12 hours. After completion of the reaction, the reaction was stopped, and the reactants were cooled to room temperature, added with water, filtered, and washed with water. The resulting solid was recrystallized and purified from toluene to obtain a white powder M1. The amount of Pd(PPh3)4 added was 1 mol% of the 2-naphthaleneboronic acid.

[0192] Into a 3L three-necked flask equipped with mechanical stirring, low temperature thermometer, 100mmol of Ml, 1L of THF were added, liquid nitrogen was used to cool the mixture to -90°C to -80°C, 250mmol of n-butyllithium was added dropwise, after the addition was completed, the mixture was kept at -90°C to -80°C for 30min, 120mmol of tributyl borate was added, and then the mixture was naturally warmed to 0°C, and the stirring was continued for 8h. After the reaction was completed, 1000mL of 10wt% aqueous ammonium chloride solution was added, the mixture was separated, the organic phase was washed with 300mL of 10wt% aqueous ammonium chloride solution each time, the filtrate was concentrated to obtain black solid, and then the black solid was crystallized with toluene to obtain yellowish sand-like solid M2.

[0193] Into a reaction flask, 100mmol of M2, 100mmol of 2-phenyl-4,6-dichloro-triazine, 41.4g of potassium carbonate (300mmol), 800mL of THF and 200mL of water were added, and 1mol% of Pd(PPh3)4 was added, and the mixture was reacted at 60°C for 12h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, and the mixture was filtered, washed with water, and the obtained solid was recrystallized with toluene to obtain white powder M3. The amount of Pd(PPh3)4 added was 1mol% of M2.

[0194] Into a reaction flask, 100mmol of M3, 100mmol of 9,9'-spirobifluorene-2-boronic acid, 41.4g of potassium carbonate (300mmol), 800mL of THF and 200mL of water were added, and 1mol% of Pd(PPh3)4 was added, and the mixture was reacted at 60°C for 12h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, and the mixture was filtered, washed with water, and the obtained solid was recrystallized with toluene to obtain white powder B2. The amount of Pd(PPh3)4 added was 1mol% of M3.

[0195] 1 H NMR (400 MHz, Chloroform) δ 9.07 (s, 1H), 8.49 (d, J = 10.0 Hz, 2H), 8.40 - 8.31 (m, 2H), 8.20 - 8.01 (m, 5H), 7.98 (d, J = 8.4 Hz, 2H), 7.92 (d, J = 8.8 Hz, 3H), 7.70 - 7.46 (m, 11H), 7.41 - 7.30 (m, 4H), 7.28-7.19 (m, 3H).

[0196] Synthesis of compound B4

[0197]

[0198] In a reaction flask, 100 mmol of 2-naphthaleneboronic acid, 100 mmol of p-bromoiodobenzene, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and reacted at 60°C for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M1. At this time, the amount of Pd(PPh3)4 added was 1 mol% of 2-naphthaleneboronic acid.

[0199] Under N2 protection, 100 mmol of M1, 1 L of THF were added to a 3 L three-necked flask equipped with mechanical stirring and a low-temperature thermometer, and the liquid nitrogen was cooled to -90 to -80°C, 250 mmol of n-butyllithium was added dropwise, and after the dropwise addition was completed, it was incubated at -90 to -80°C for 30 min, 120 mmol of tributyl borate was added, and after the addition was completed, it was naturally warmed to zero, and stirring was continued for 8 h. After the reaction was completed, 1000 mL of 10 wt% aqueous ammonium chloride solution was added, and the organic phase was washed with 300 mL of 10 wt% aqueous ammonium chloride solution each time, and the filtrate was concentrated to obtain a black solid, which was crystallized with toluene to obtain a light yellow sandy solid M2.

[0200] In a reaction flask, 200 mmol of M2, 100 mmol of 2-phenyl-4,6-dichloro-triazine, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF and 200 mL of water were added, and 2 mol% of Pd(PPh3)4 was added, and reacted at 60°C for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder B4. At this time, the amount of Pd(PPh3)4 added was 2 mol% of M2.

[0201] 1 H NMR (400 MHz, Chloroform) δ 8.40-8.31 (m, 2H), 8.08 (t, J = 9.2 Hz, 4H), 7.97 (t, J = 8.4 Hz, 6H), 7.65-7.46 (m, 9H), 7.37 (d, J = 8.0 Hz, 2H), 7.22 (d, J = 8.4 Hz, 4H).

[0202] Synthesis of compound B6

[0203]

[0204] In a reaction flask, 100 mmol of 2-naphthaleneboronic acid, 100 mmol of p-bromoiodobenzene, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and the reaction was performed at 60°C for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M1. Herein, the amount of Pd(PPh3)4 added was 1 mol% of 2-naphthaleneboronic acid.

[0205] Under N2 protection, 100 mmol of M1, 1 L of THF were added to a 3 L three-necked flask equipped with a mechanical stirrer and a low-temperature thermometer, and the temperature was lowered to -90 to -80°C with liquid nitrogen, 250 mmol of n-butyllithium was added dropwise, and after the dropwise addition was completed, the temperature was maintained at -90 to -80°C for 30 min, 120 mmol of tributyl borate was added, and after the addition was completed, the temperature was naturally increased to zero, and stirring was continued for 8 h. After the reaction was completed, 1000 mL of 10 wt% aqueous ammonium chloride solution was added, and the organic phase was washed with 300 mL of 10 wt% aqueous ammonium chloride solution each time, and the filtrate was concentrated to obtain a black solid, which was crystallized with toluene to obtain a light yellow sandy solid M2.

[0206] In a reaction flask, 100 mmol of M2, 100 mmol of 2-phenyl-4,6-dichloro-triazine, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and the reaction was performed at 60°C for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M3. Herein, the amount of Pd(PPh3)4 added was 1 mol% of M2.

[0207] In a reaction flask, 100 mmol of 2-bromofluorenone, 1000 mmol of phenol were added, and heated to reflux, and the reaction was performed for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M4.

[0208] In a reaction flask, 100 mmol of M4, 100 mmol of pinacol diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of xylene, and 1 mol% of Pd(PPh3)4 were added, and the reaction was performed at 100°C for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M5. Herein, the amount of Pd(PPh3)4 added was 1 mol% of M4.

[0209] In a reaction bottle, 100 mmol of M3, 100 mmol of M5, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and reacted at 60°C for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder B6. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of M3.

[0210] 1 H NMR (400 MHz, Chloroform) δ 8.41 - 8.32 (m, 2H), 8.26 (s, 1H), 8.11 (t, J = 8.8 Hz, 3H), 8.02 (t, J = 9.2 Hz, 3H), 7.91 (d, J = 9.2 Hz, 1H), 7.80 (d, J = 8.4 Hz, 1H), 7.69 - 7.45 (m, 7H), 7.42 - 7.16 (m, 11H), 7.03 (t, J = 8.0 Hz, 2H).

[0211] Synthesis of compound B7

[0212]

[0213] In a reaction bottle, 100 mmol of 2-naphthalene boronic acid, 100 mmol of p-bromoiodobenzene, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and reacted at 60°C for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M1. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of 2-naphthalene boronic acid.

[0214] Under N2 protection, 100 mmol of M1, 1 L of THF were added to a 3 L three-necked flask equipped with mechanical stirring, low-temperature thermometer, and liquid nitrogen was cooled to -90°C to -80°C, 250 mmol of n-butyllithium was added dropwise, and after the addition was completed, it was incubated at -90°C to -80°C for 30 min, 120 mmol of tributyl borate was added, and after the addition was completed, it was naturally warmed to zero, and stirring was continued for 8 h. After the reaction was completed, 1000 mL of 10 wt% aqueous ammonium chloride solution was added, and the organic phase was washed with 300 mL of 10 wt% aqueous ammonium chloride solution each time, and the filtrate was concentrated to obtain a black solid, which was crystallized with toluene to obtain a light yellow sandy solid M2.

[0215] In a reaction flask, 100 mmol of M2, 100 mmol of 2-phenyl-4,6-dichloro-triazine, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and reacted at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M3. At this time, the amount of Pd(PPh3)4 added was 1 mol% of M2.

[0216] In a reaction flask, 100 mmol of 2-bromo-9,10-diphenylphenylfluorene, 100 mmol of pinacol diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of xylene, and 1 mol% of Pd(PPh3)4 were added, and reacted at 100°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M4. At this time, the amount of Pd(PPh3)4 added was 1 mol% of 2-bromo-9,10-diphenylphenylfluorene.

[0217] In a reaction flask, 100 mmol of M3, 100 mmol of M4, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and reacted at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder B7. At this time, the amount of Pd(PPh3)4 added was 1 mol% of M3.

[0218] 1 H NMR (400 MHz, Chloroform) δ 8.56 (s, 1H), 8.45 (d, J = 11.2 Hz, 1H), 8.40-8.31 (m, 2H), 8.26 (s, 1H), 8.14 (s, 1H), 8.08 (t, J = 8.8 Hz, 2H), 8.02-7.94 (m, 5H), 7.82 (d, J = 7.6 Hz, 1H), 7.65-7.35 (m, 9H), 7.30-7.15 (m, 8H), 7.10 (d, J = 8.0 Hz, 4H).

[0219] Synthesis of compound B15

[0220]

[0221] In a reaction flask, 100 mmol of phenylboronic acid, 100 mmol of 2,6-dibromonaphthalene, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and the reaction was performed at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M1. Herein, the amount of Pd(PPh3)4 added was 1 mol% of phenylboronic acid.

[0222] In a reaction flask, 100 mmol of M1, 100 mmol of p-chlorophenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and the reaction was performed at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M2. Herein, the amount of Pd(PPh3)4 added was 1 mol% of M1.

[0223] In a reaction flask, 100 mmol of M2, 100 mmol of pinacol diboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of xylene, and 1 mol% of Pd(PPh3)4 were added, and the reaction was performed at 100°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M3. Herein, the amount of Pd(PPh3)4 added was 1 mol% of M2.

[0224] In a reaction flask, 100 mmol of M3, 100 mmol of 2-phenyl-4,6-dichloro-triazine, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and the reaction was performed at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M4. Herein, the amount of Pd(PPh3)4 added was 1 mol% of M3.

[0225] In a reaction flask, 100 mmol of 2-bromospirofluorene, 100 mmol of p-chlorobenzeneboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and reacted at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M5. At this time, the amount of Pd(PPh3)4 added was 1 mol% of 2-bromospirofluorene.

[0226] In a reaction flask, 100 mmol of M5, 100 mmol of pinacol diboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of xylene, and 1 mol% of Pd(PPh3)4 were added, and reacted at 100°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder M6. At this time, the amount of Pd(PPh3)4 added was 1 mol% of M5.

[0227] In a reaction flask, 100 mmol of M4, 100 mmol of M6, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF and 200 mL of water were added, and 1 mol% of Pd(PPh3)4 was added, and reacted at 60°C for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder B15. At this time, the amount of Pd(PPh3)4 added was 1 mol% of M4.

[0228] 1 H NMR (400 MHz, Chloroform) δ 8.51 (s, 1H), 8.39-8.31 (m, 2H), 8.09 (d, J = 8.4 Hz, 1H), 8.05 (d, J = 8.0 Hz, 2H), 7.96 (d, J = 8.8 Hz, 4H), 7.95-7.87 (m, 3H), 7.81-7.72 (m, 6H), 7.55-7.30 (m, 11H), 7.28-7.19 (m, 9H).

[0229] Other compounds according to the present application can be synthesized by selecting appropriate starting materials according to the above synthesis example, or any other appropriate method and starting materials can be used for synthesis.

[0230] Example

[0231] The following examples and comparative examples are provided to more specifically illustrate the embodiments of the present invention. Various tests and evaluations were performed according to the following methods. In addition, unless otherwise specified, "parts" and "%" are based on mass.

[0232] Example 1

[0233] A glass substrate coated with a 150nm thick ITO transparent conductive layer was ultrasonically treated in a commercial detergent, rinsed in deionized water, ultrasonically degreased in an acetone-ethanol mixed solvent, baked in a clean environment to completely remove moisture, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam to obtain a glass substrate with an anode.

[0234] Then, the glass substrate with the anode is placed in a vacuum chamber and evacuated to less than 10 -5 A first hole injection layer is vacuum-deposited on the anode layer film of the glass substrate with an anode. The materials of the first hole injection layer include hole injection layer material HT-11 and p-type dopant p-1. The deposition is performed by a multi-source co-evaporation method. The deposition rate of the hole injection layer material HT-11 is adjusted to 0.1 nm / s, and the deposition rate of the p-type dopant p-1 is adjusted to 3% of the deposition rate of the hole injection layer material HT-11. The total deposition thickness is 10 nm. The hole injection layer material HT-11 and the p-type dopant p-1 are as follows:

[0235]

[0236] Then, a hole transport material HT-5 was vacuum evaporated on the first hole injection layer to form a first hole transport layer. The evaporation rate was 0.1 nm / s and the evaporation film thickness was 80 nm. The hole transport material HT-5 was as follows:

[0237]

[0238] Then, a first light-emitting layer was vacuum-deposited on the first hole transport layer. The first light-emitting layer included a host material BH-2 and a guest material BD-1. The deposition was performed using a multi-source co-evaporation method. The deposition rate of the host material BH-2 was adjusted to 0.1 nm / s, and the deposition rate of the guest material BD-1 was adjusted to 3% of the deposition rate of the host material BH-2. The total deposition thickness was 30 nm. The host material BH-2 and the guest material BD-1 were as follows:

[0239]

[0240] Then, a first electron transport layer is vacuum evaporated on the first light emitting layer, and the compound B4 provided by the application and LiQ are evaporated to form the first electron transport layer, wherein the evaporation rate of the compound B4 is 0.1 nm / s, the evaporation ratio of the compound B4 to LiQ is 50:50, and the total evaporation film thickness is 30 nm; the compound B4 is as follows:

[0241]

[0242] The first hole injection layer, the first hole transport layer, the first light emitting layer and the first electron transport layer together form a first light emitting unit;

[0243] On the first electron transport layer of the uppermost layer in the first light emitting unit, the compound A1 provided by the application and metal ytterbium (Yb) are evaporated to form a charge generation layer, wherein the evaporation rate of the compound A1 is 0.01 nm / s, the evaporation rate ratio of the compound A1 to Yb is 99:1, and the total evaporation film thickness is 10 nm;

[0244] A second hole injection layer is evaporated on the charge generation layer, and the material of the second hole injection layer includes a hole injection layer material HT-11 and a p-type dopant p-1, wherein the evaporation rate of the hole injection layer material HT-11 is adjusted to be 0.1 nm / s, the evaporation rate ratio of the hole injection layer material HT-11 to the p-type dopant p-1 is 99:1, and the total evaporation film thickness is 10 nm;

[0245] Then, a hole transport material HT-5 is vacuum evaporated on the second hole injection layer as a second hole transport layer, wherein the evaporation rate is 0.1 nm / s, and the evaporation film thickness is 80 nm;

[0246] Then, a second light emitting layer is vacuum evaporated on the second hole transport layer, and the second light emitting layer includes a host material BH-2 and a guest material BD-1, and the evaporation is performed by a multi-source co-evaporation method, wherein the evaporation rate of the host material BH-2 is adjusted to be 0.1 nm / s, the evaporation rate of the guest material BD-1 is 3% of the evaporation rate of the host material BH-2, and the total evaporation film thickness is 30 nm;

[0247] Then, a second electron transport layer is vacuum evaporated on the second light emitting layer, and the compound B4 provided by the application and LiQ are evaporated to form the second electron transport layer, wherein the evaporation rate of the compound B4 is 0.1 nm / s, the evaporation ratio of the compound B4 to LiQ is 50:50, and the total evaporation film thickness is 30 nm;

[0248] The second hole injection layer, the second hole transport layer, the second light emitting layer and the second electron transport layer together form a second light emitting unit;

[0249] Then, LiF with a thickness of 5 nm was vacuum-evaporated as an electron injection layer on the second electron transport layer of the uppermost layer in the second light-emitting unit, wherein the evaporation rate was 0.1 nm / s.

[0250] Finally, an Al layer with a thickness of 150 nm was vacuum-evaporated as a cathode electrode of the organic electroluminescent device on the electron injection layer, wherein the evaporation rate was 0.1 nm / s.

[0251] Examples 2 to 7

[0252] Except that the charge generation layer was replaced by A4, A5, A7, A10, A15, A23 respectively instead of A1, the rest was the same as Example 1. See Table 1 for details.

[0253] Examples 8 to 11

[0254] Except that the first electron transport layer and the second electron transport layer were replaced by B2, B6, B7, B15 respectively instead of B4, the rest was the same as Example 1. See Table 1 for details.

[0255] Example 12

[0256] Except that the first electron transport layer and the second electron transport layer were replaced by an electron transport layer evaporated by compound B4 and LiQ, wherein the evaporation rate of compound B4 was 0.1 nm / s, the evaporation ratio of compound B4 and LiQ was 80:20, and the total film thickness of evaporation was 30 nm, the rest was the same as Example 1.

[0257] Example 13

[0258] Except that the first electron transport layer and the second electron transport layer were replaced by an electron transport layer evaporated by compound B4 and LiQ, wherein the evaporation rate of compound B4 was 0.1 nm / s, the evaporation ratio of compound B4 and LiQ was 20:80, and the total film thickness of evaporation was 30 nm, the rest was the same as Example 1.

[0259] Comparative Example 1

[0260] Except that the charge generation material was selected as CGL00R1 instead of A1, and the electron transport layer was selected as ET-12 instead of B4, the rest was the same as Example 1. The charge generation material CGL00R1 and the electron transport material ET-12 were as follows:

[0261]

[0262] Comparative Example 2

[0263] Except that the charge generation material was selected as CGL00R1 instead of A1, the rest was the same as Example 1.

[0264] Comparative Example 3

[0265] Except that the electron transport material is replaced by ET-12 instead of B4, the rest is the same as Example 1.

[0266] The organic electroluminescent devices prepared by the above process were subjected to the following performance measurements:

[0267] The driving voltage, current efficiency and device lifetime of the organic electroluminescent devices prepared in Example 1 to Example 13 and Comparative Example 1 to Comparative Example 3 were measured at the same brightness using a digital source table and a luminance meter. Specifically, the voltage was increased at a rate of 0.1 V per second, and the voltage when the brightness of the organic electroluminescent device reached 1000 cd / m 2 was measured as the driving voltage, and the current density at this time was also measured; the ratio of brightness to current density was the current efficiency; the LT95 lifetime test was as follows: at 1000 cd / m 2 , a constant current was maintained, and the time for the brightness of the organic electroluminescent device to decrease to 950 cd / m 2 was measured in hours. The results are shown in Table 1.

[0268] Table 1 Performance results of organic electroluminescent devices

[0269]

[0270]

[0271] As can be seen from Table 1, the organic electroluminescent devices prepared in Example 1 to Example 13 of the present application use the compounds A1, A4, A5, A7, A10, A15, A23 of the present application as charge generation materials, and use the compounds B2, B4, B6, B7, B15 of the present application as electron transport materials. Compared with the known materials in the prior art used as charge generation materials and electron transport materials in the organic electroluminescent devices in Comparative Example 1, the known material used as a charge generation material in Comparative Example 2, and the known material used as an electron transport material in Comparative Example 3, the organic electroluminescent devices of the present application have lower driving voltage, higher current efficiency and longer LT95 lifetime. Therefore, it is shown that the use of the compound of formula (I) as a charge generation material and the compound of formula (II) as an electron transport material in an organic electroluminescent device can effectively reduce the driving voltage, improve the current efficiency and prolong the service life of the device. The materials of the present application have significantly improved performance in improving efficiency and prolonging lifetime, and are good electroluminescent devices.

[0272] It can be understood that the organic electroluminescence devices in Embodiment 1 to Embodiment 13 are blue organic electroluminescence devices, and the above embodiments are only examples, and the compounds provided by the application can be used as electron transport materials and charge generation materials, and can also be applied to red organic electroluminescence devices and green organic electroluminescence devices to reduce the driving voltage of the red organic electroluminescence devices and the green organic electroluminescence devices, improve the luminous efficiency thereof, and prolong the service life thereof.

[0273] The above only describes the preferred embodiments of the present application and is not intended to limit the present application. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present application shall be included in the scope of protection of the present application.

Claims

1. An organic electroluminescent device comprising a charge generation layer and an electron transport layer; The charge generation layer comprises a compound of formula (I): in, L 1 and L 2 Each independently selected from a chemical bond, a C6-C 30 Arylene, unsubstituted or Rc-substituted C3-C 30 heteroarylene; X 1 -X 10 is selected from CR or N, R is selected from hydrogen, deuterium, C1-C4 alkyl, C2-C6 alkenyl, amine, hydroxyl, C6-C6 unsubstituted or substituted by Rc 30 Aryl, unsubstituted or Rc-substituted C3-C 30 Heteroaryl, and adjacent R can be connected to form a ring, and X 1 -X 10 At least one of them is N; The electron transport layer comprises a compound of formula (II): in, Ar 1 and Ar 2 Each independently selected from C6-C 30 Aryl, unsubstituted or Rc-substituted C3-C 30 Heteroaryl, and at least one selected from C6-C 30 aryl; X 11 -X 13 Each is independently selected from CH or N, and at least two are selected from N; R 1 and R 2 Each independently selected from hydrogen, C6-C 30 Aryl, unsubstituted or Rc-substituted C3-C 30 heteroaryl; L is selected from a chemical bond, an unsubstituted or Rc-substituted C6-C 30 Arylene, unsubstituted or Rc-substituted C3-C 30 heteroarylene; The heteroatoms on the heteroaryl or the heteroarylene are each independently selected from O, S or N; The substituents Rc of each group are each independently selected from deuterium, halogen, nitro, cyano, C1-C4 alkyl, phenyl, biphenyl, terphenyl, pyrimidinyl or naphthyl.

2. The organic electroluminescent device according to claim 1, wherein The compound of formula (I) is used in combination with a metal-containing material, and the content of the metal-containing material accounts for 0.5%-2.5% of the charge generation layer; the metal-containing material is selected from at least one of a metal and a metal complex; the metal is selected from at least one of Li and Yb, and the metal complex is selected from at least one of LiQ and AlQ3.

3. The organic electroluminescent device according to claim 1, wherein The charge generation layer has a thickness of 10 nm to 30 nm.

4. The organic electroluminescent device according to claim 1, wherein The thickness of the electron transport layer is 10 nm to 40 nm.

5. The organic electroluminescent device according to claim 1, wherein The compound of formula (II) is used in combination with LiQ, and the content of LiQ accounts for 10%-90% of the content of the electron transport layer. The organic electroluminescent device according to claim 1 , wherein: The compound of formula (I) is selected from the following compounds A1 to A30:

7. The organic electroluminescent device according to claim 1, wherein The compound of formula (II) is selected from the following compounds B1 to B22:

8. A display device comprising the organic electroluminescent device according to any one of claims 1 to 7.

Images