Cyano-substituted phenanthroline compound and application thereof

Abstract

The invention relates to the technical field of organic light-emitting display, in particular to a cyano-substituted phenanthroline compound and application thereof. The invention provides an organic electroluminescent device, which comprises a charge generation layer, and the material of the charge generation layer comprises a compound of formula (I). According to the organic light-emitting device provided by the invention, the material of the charge generation layer is the cyano-substituted phenanthroline compound, has efficient charge generation capability, can effectively improve the light-emitting efficiency of the organic light-emitting device, has a relatively deep energy level, and can be better matched with the material of the adjacent layer for use, so that the light-emitting efficiency of the organic light-emitting device is improved. The charge transmission performance of the organic light-emitting device can be effectively improved, the light-emitting efficiency of the organic light-emitting device is improved, the driving voltage of the organic light-emitting device is reduced, and the service life of the organic light-emitting device is prolonged.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of organic light-emitting display, in particular to a cyano-substituted phenanthroline compound and application thereof. BACKGROUND

[0002] Electroluminescence (EL) refers to a phenomenon that a luminescent material emits light under the action of an electric field, is excited by current and voltage, and is a light-emitting process 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 a liquid crystal display, the organic electroluminescent display does not need a backlight source, has a large viewing angle, low power, and a response speed of up to 1000 times that of a liquid crystal display, and the manufacturing cost is lower than that of a liquid crystal display with the same resolution. Therefore, the organic electroluminescent device has a very broad application prospect.

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

[0004] The purpose of the present application is to provide a cyano-substituted phenanthroline compound and application thereof, so as to improve the luminous efficiency of the organic electroluminescent device and prolong its service life.

[0005] The first aspect of the present application provides a cyano-substituted phenanthroline compound having a structure as shown in formula (I):

[0006]

[0007] Ar1 is selected from C6-C12 aryl unsubstituted or substituted with Rc, C3-C12 heteroaryl unsubstituted or substituted with Rc, or C1-C12 alkyl unsubstituted or substituted with Rc; 30 C6-C12 aryl unsubstituted or substituted with Rc, C3-C12 heteroaryl unsubstituted or substituted with Rc, or C1-C12 alkyl unsubstituted or substituted with Rc; 30 C3-C12 heteroaryl unsubstituted or substituted with Rc, or C1-C12 alkyl unsubstituted or substituted with Rc;

[0008] L1, L2 are each independently selected from a chemical bond, C6-C12 arylene unsubstituted or substituted with Rc, C3-C12 heteroarylene unsubstituted or substituted with Rc, or C1-C12 alkylene unsubstituted or substituted with Rc; 30 C6-C12 arylene unsubstituted or substituted with Rc, C3-C12 heteroarylene unsubstituted or substituted with Rc, or C1-C12 alkylene unsubstituted or substituted with Rc; 30heteroaryl;

[0009] A is selected from the following excerpt:

[0010]

[0011] The heteroatoms on the heteroaryl group or the heteroalkylene group are each independently selected from O, S or N;

[0012] The substituents Rc of each group are independently selected from hydrogen, deuterium, halogen, nitro, cyano, C1-C4 alkyl, phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl, or naphthyl.

[0013] Preferably, Ar1 is selected from the groups of the following compounds that are unsubstituted or Rc-substituted: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, fluoranthene, anthracene, dibenzofuran, dibenzothiophene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, spirofluorene, pyridine, quinoline, quinazoline, pyrimidine, triazine, phenanthrene, carbazole, and phosphoxy.

[0014] Preferably, L1 and L2 are each independently chemically bonded, unsubstituted, or Rc-substituted groups of the following compounds: phenyl, pyridinyl, pyrimidinyl, quinoxalinyl, quinazolinyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, fluorenyl, anthraceneyl, dibenzofuranyl, dibenzothiopheneyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl.

[0015] More preferably, the cyano-substituted phenanthroline compound is selected from the compounds shown in A1 to A40 below:

[0016]

[0017]

[0018] A second aspect of the present invention provides an organic electroluminescent device comprising a charge generating layer, wherein the charge generating layer material comprises at least one of the cyano-substituted phenanthroline compounds described in the first aspect of the present invention.

[0019] Preferably, the charge-generating layer material comprises metallic Li or Yb, and the mass percentage of metallic Li or Yb is 0.5%-15% based on the mass of the charge-generating layer material.

[0020] More preferably, the thickness of the charge generation layer is 10nm-30nm.

[0021] A third aspect of the present invention provides a display device comprising the organic electroluminescent device described in the second aspect of the present invention.

[0022] Compared with the prior art, the beneficial effects of the present invention are as follows:

[0023] The organic electroluminescent device provided by this invention uses a charge generation layer material comprising a cyano-substituted phenanthroline compound, which exhibits highly efficient charge generation capability, effectively improving the luminous efficiency of the organic electroluminescent device. The HOMO and LUMO energy levels are deepened due to the introduction of cyano segments, making it more suitable for pairing with the P-CGL layer material. This effectively enhances the charge transport performance of the organic electroluminescent device, improves its luminous efficiency, reduces its driving voltage, and extends its lifespan. The display device provided by this invention has excellent display performance.

[0024] Of course, implementing any product or method of the present invention does not necessarily require achieving all of the advantages described above at the same time. Attached Figure Description

[0025] To more clearly illustrate the technical solutions of this invention, the accompanying drawings used in the description of the embodiments will be briefly introduced below. Obviously, the drawings described below are only some embodiments of this invention. For those skilled in the art, other embodiments can be obtained based on these drawings.

[0026] Figure 1 This is a schematic diagram of a typical organic electroluminescent device.

[0027] The reference numerals in the figures are as follows: 20, organic electroluminescent device; 21, substrate; 22, reflective anode; 231, first hole injection layer; 241, first hole transport layer; 251, first light-emitting layer; 261, first electron transport layer; 27, charge generation layer; 232, second hole injection layer; 242, second hole transport layer; 252, second light-emitting layer; 262, second electron transport layer; 28, electron injection layer; 29, cathode electrode. Detailed Implementation

[0028] The technical solutions of this invention will now be clearly and completely described with reference to the accompanying drawings. Obviously, the described embodiments are merely some, not all, of the embodiments of this invention. All other embodiments obtained by those skilled in the art based on this invention are within the scope of protection of this invention.

[0029] A first aspect of the present invention provides a cyano-substituted phenanthroline compound having a structure as shown in formula (I):

[0030]

[0031] Ar1 is selected from unsubstituted or Rc-substituted C6-C. 30 Aryl, unsubstituted or Rc-substituted C3-C 30 Mixed aromatics;

[0032] L1 and L2 are each independently selected from chemical bonds, and are either unsubstituted or Rc-substituted C6-C bonds. 30 aryl, unsubstituted or Rc-substituted C3-C 30 heteroaryl;

[0033] A is selected from the following excerpt:

[0034]

[0035] The heteroatoms on the heteroaryl group or the heteroalkylene group are each independently selected from O, S or N;

[0036] The substituents Rc of each group are independently selected from hydrogen, deuterium, halogen, nitro, cyano, C1-C4 alkyl, phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl, or naphthyl.

[0037] In a preferred embodiment, Ar1 is selected from the groups of the following compounds that are unsubstituted or Rc-substituted: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, fluoranthene, anthracene, dibenzofuran, dibenzothiophene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, spirofluorene, pyridine, quinoline, quinazoline, pyrimidine, triazine, phenanthrene, carbazole, and phosphoxy.

[0038] In some preferred embodiments, L1 and L2 are each independently chemically bonded, unsubstituted, or Rc-substituted groups of the following compounds: phenyl, pyridinyl, pyrimidinyl, quinoxalinyl, quinazolinyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, fluorenyl, anthraceneyl, dibenzofuranyl, dibenzothiopheneyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl.

[0039] As a preferred embodiment, the cyano-substituted phenanthroline compound is selected from the compounds shown in A1 to A40 below:

[0040]

[0041]

[0042] A second aspect of the present invention provides an organic electroluminescent device comprising a charge generating layer, wherein the charge generating layer material comprises at least one of the cyano-substituted phenanthroline compounds described in the first aspect of the present invention.

[0043] In a preferred embodiment, the charge-generating layer material comprises metallic Li or Yb, and the mass percentage of metallic Li or Yb is 0.5%-15% based on the mass of the charge-generating layer material.

[0044] In some preferred embodiments, the thickness of the charge generation layer is 10nm-30nm.

[0045] In this invention, there are no particular limitations on the type and structure of organic electroluminescent devices. They can be organic electroluminescent devices of different types and structures known in the art, as long as at least one of the charge-generating materials provided by this invention can be used.

[0046] In one embodiment of the present invention, the organic electroluminescent device includes an anode and a cathode, with m light-emitting units stacked between the anode and the cathode, and m-1 charge-generating layers located between two adjacent light-emitting units. Each charge-generating layer includes an n-type charge-generating layer and a p-type charge-generating layer, where m is an integer ≥2. Each light-emitting unit includes at least one light-emitting layer, and the maximum emission wavelength of light emitted in different light-emitting units is different. At least one of the n-type charge-generating layers includes at least one compound of formula (I) and a metal-containing material, wherein the metal-containing material includes metals, metal complexes, or combinations thereof.

[0047] In one embodiment of the present invention, the light-emitting unit in the organic electroluminescent device may include a first light-emitting unit and a second light-emitting unit, which may be the same or different; a charge-generating layer may be disposed between the first light-emitting unit and the second light-emitting unit, the first light-emitting unit may be disposed between the anode and the charge-generating layer, and the second light-emitting unit may be disposed between the charge-generating layer and the cathode. The n-type charge-generating layer of the charge-generating layer may include at least one compound of formula (I) and a metal-containing material. The second light-emitting unit may also include an electron transport layer between the light-emitting layer and the cathode of the second light-emitting unit.

[0048] In one embodiment of the present invention, in an organic electroluminescent device with a light-emitting unit of 2, the first light-emitting unit may further include an HT-light-emitting auxiliary layer between the light-emitting layer and the anode of the first light-emitting unit, and the first light-emitting unit includes an electron transport layer.

[0049] In other embodiments of the present invention, the organic electroluminescent device of the present invention may be a top-emitting structure light-emitting device, which may include, in sequence on a substrate, an anode, a first light-emitting unit, a charge-generating layer, a second light-emitting unit, an electron injection layer, and a transparent or semi-transparent cathode.

[0050] The organic electroluminescent device of the present invention can also be a bottom-emitting device, which may include 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 sequentially on a substrate.

[0051] The organic electroluminescent device of the present invention can also be a light-emitting device with a dual-sided light-emitting structure, which may include, in sequence on a substrate, a transparent or semi-transparent anode, a first light-emitting unit, a charge-generating layer, a second light-emitting unit, an electron injection layer, and a transparent or semi-transparent cathode.

[0052] 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 arranged in sequence, 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 arranged in sequence.

[0053] Furthermore, the organic electroluminescent device of the present invention may have an electron blocking layer between the hole transport layer and the light-emitting layer, and a hole blocking layer between the light-emitting layer and the electron transport layer. A light extraction layer may be disposed on the transparent electrode on the light-emitting side. However, the structure of the organic electroluminescent device of the present invention is not limited to the specific structure described above. If necessary, the above-mentioned layers may be omitted or added. The present invention does not impose any particular limitation on the thickness of the above-mentioned anode, hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron injection layer, cathode, and light extraction layer, as long as the purpose of the present invention can be achieved. For example, an organic electroluminescent device may sequentially comprise, on a substrate, an anode (100nm to 150nm) made of metal, a first hole injection layer (5nm to 20nm), a first hole transport layer (80nm to 140nm), an electron blocking layer (5nm to 20nm), a first light-emitting layer (15nm to 40nm), a hole blocking layer (5nm to 20nm), a first electron transport layer (10nm to 40nm), a charge generation layer (10nm to 30nm), a second hole injection layer (5nm to 20nm), a second hole transport layer (80nm to 140nm), a second light-emitting layer (15nm to 40nm), a second electron transport layer (10nm to 40nm), an electron injection layer (5nm to 20nm), a transparent or semi-transparent cathode, and a light extraction layer (50nm to 90nm). Exemplarily, Figure 1 A schematic diagram of a typical organic electroluminescent device 20 is shown, in which, from bottom to top, a substrate 21, a reflective anode 22, a first hole injection layer 231, a first hole transport layer 241, a first light-emitting layer 251, a first electron transport layer 261, a charge generation layer 27, a second hole injection layer 232, a second hole transport layer 242, a second light-emitting layer 252, a second electron transport layer 262, an electron injection layer 28, and a cathode electrode 29 are sequentially arranged. It can be understood that... Figure 1 The structure of a typical organic electroluminescent device is shown only schematically. The present invention is not limited to this structure, and the charge generation layer material of the present invention can be used in any type of organic electroluminescent device.

[0054] For convenience, the organic electroluminescent device of the present invention will be described below, but this does not imply any limitation on the scope of protection of the present invention. It is understood that all organic electroluminescent devices using the charge generation layer material or electron transport layer material of the present invention are within the scope of protection of the present invention.

[0055] In this invention, there are no particular limitations on the substrate 21. Conventional substrates used in organic electroluminescent devices in the prior art can be used, such as glass, polymer materials, and glass and polymer materials with thin-film transistor (TFT) components.

[0056] In this invention, there are no particular limitations on the material of the reflective anode 22. It can be selected from transparent conductive materials known in the prior art such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), and zinc oxide (ZnO), or metallic materials such as silver and its alloys, aluminum and its alloys, or organic conductive materials such as poly(3,4-ethylenedioxythiophene) (PEDOT). Alternatively, the reflective anode 22 can be a multilayer structure formed from the above materials. This invention does not have any particular limitation on the number of layers in the multilayer structure. The number of layers can be selected according to actual needs, as long as the purpose of this invention is met. For example, one layer, two layers, three layers, or more layers.

[0057] In this invention, there are no particular limitations on the materials of the first hole injection layer 231 and the second hole injection layer 232. They can be made of hole injection layer materials known in the art or hole transport layer materials (HTM) known in the art. For example, at least one of the known hole transport layer materials (HTM) can be selected as the hole injection layer material.

[0058] In this invention, the first hole injection layer 231 and the second hole injection layer 232 may further include p-type dopants. This invention does not particularly limit the type of p-type dopant, and various p-type dopants known in the art can be used. For example, the p-type dopant may be selected from, but is not limited to, at least one of the following p-1 to p-3 compounds:

[0059]

[0060] In this invention, there are no particular restrictions on the amount of p-type dopant used, and the amount can be any amount known to those skilled in the art.

[0061] In this invention, there are no particular limitations on the materials of the first hole transport layer 241 and the second hole transport layer 242, and they can be made of hole transport layer materials (HTM) known in the art. This invention does not particularly limit the number of hole transport layers, and it can be adjusted according to actual needs, as long as the purpose of this invention is met; for example, one, two, three, four, or more layers.

[0062] For example, HTM for hole injection layer materials and HTM for hole transport layer materials can be selected from, but are not limited to, at least one of the following HT-1 to HT-31 compounds:

[0063]

[0064]

[0065] In this invention, there are no particular restrictions on the materials of the first light-emitting layer 251 and the second light-emitting layer 252. Each of them may contain a main material for the light-emitting layer and a guest material for the light-emitting layer. There are no particular restrictions on the amount of the main material for the light-emitting layer and the guest material for the light-emitting layer. They may be amounts known to those skilled in the art.

[0066] In this invention, the light-emitting layer may include a blue light-emitting layer, a green light-emitting layer, or a red light-emitting layer. There are no particular limitations on the light-emitting material in the light-emitting layer, and various light-emitting materials known to those skilled in the art can be used.

[0067] In this invention, there are no particular limitations on the host material of the light-emitting layer, and at least one of the host materials of the light-emitting layer known in the art can be used. For example, at least one of the following compounds, but not limited to BH-1 to BH-10, can be used:

[0068]

[0069] In this invention, there are no particular limitations on the guest material of the luminescent layer, and at least one of the luminescent layer guest materials known in the art can be used. For example, the luminescent layer guest material can be selected from, but is not limited to, at least one of the following BD-1 to BD-9 compounds:

[0070]

[0071]

[0072] In this invention, the first electron transport layer 261 and the second electron transport layer 262 comprise at least one of the electron transport layer materials of this invention, or may comprise a combination of at least one of the electron transport layer materials of this invention and at least one of known electron transport materials. There is no particular limitation on the number of electron transport layers; it can be adjusted according to actual needs, as long as the purpose of this invention is met. For example, one, two, three, four, or more layers.

[0073] For example, it is known that electron transport materials can be selected from, but are not limited to, at least one of the following ET-1 to ET-57 compounds:

[0074]

[0075]

[0076]

[0077]

[0078] In this invention, the first electron transport layer 261 and the second electron transport layer 262 may each include an n-type dopant. There is no particular limitation on the type of n-type dopant, and various n-type dopants known in the art can be used. For example, the following n-type dopant, lithium 8-hydroxyquinoline (LiQ), can be used:

[0079]

[0080] In this invention, there are no particular restrictions on the amount of n-type dopant used, and the amount can be any amount known to those skilled in the art.

[0081] In this invention, the charge generation layer 27 may contain at least one of the charge generation layer materials of this invention, or may contain a combination of at least one of the charge generation layer materials of this invention and at least one of the known charge generation materials.

[0082] For example, known charge-generating materials may be selected from, but are not limited to, at least one of the following CGL00R1 to CGL00R5 compounds:

[0083]

[0084] In this invention, there are no particular limitations on the material of the electron injection layer 28. Known electron injection layer materials in the art can be used, such as at least one of the following materials in the prior art, including but not limited to lithium 8-hydroxyquinoline (LiQ), LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, etc.

[0085] In this invention, there are no particular restrictions on the material of the cathode electrode 29, which can be selected from, but is not limited to, magnesium-silver mixtures, LiF / Al, ITO, Al and other metals, metal mixtures, oxides and the like.

[0086] There are no particular limitations on the method for preparing the organic electroluminescent device of the present invention, and any method known in the art can be used. For example, the present invention can be prepared by the following method:

[0087] The method for preparing organic electroluminescent devices according to the present invention may also include, but is not limited to, the following steps:

[0088] (1) Clean the reflective anode 22 on the substrate 21 of the top-emitting organic electroluminescent device. In the cleaning machine, the anode is cleaned by chemical washing, water washing, brushing, high-pressure water washing, air knife and other steps, and then heated.

[0089] (2) Hole injection material is vacuum-deposited on the reflective anode 22 as the first hole injection layer 231;

[0090] (3) A hole transport layer material is vacuum-deposited on the first hole injection layer 231 to serve as the first hole transport layer 241;

[0091] (4) A first light-emitting layer 251 is vacuum-deposited on the first hole transport layer 241, the light-emitting layer containing a light-emitting layer host material and a light-emitting layer guest material;

[0092] (5) Vacuum evaporation of electron transport material on the first light-emitting layer 251 serves as the first electron transport layer 261;

[0093] (6) A charge-generating material is vacuum-deposited on the first electron transport layer 261 as a charge-generating layer 27;

[0094] (7) Vacuum vapor deposition of hole injection material on charge generation layer 27 as second hole injection layer 232;

[0095] (8) Vacuum evaporation of hole transport layer material on the second hole injection layer 232 serves as the second hole transport layer 242;

[0096] (9) A second light-emitting layer 252 is vacuum-deposited on the second hole transport layer 242, the light-emitting layer containing a light-emitting layer host material and a light-emitting layer guest material;

[0097] (10) Vacuum evaporation of electron transport material on the second light-emitting layer 252 serves as the second electron transport layer 262;

[0098] (11) Vacuum evaporation of electron injection material on the second electron transport layer 262 serves as electron injection layer 28;

[0099] (12) A cathode material is vacuum-deposited on the electron injection layer 28 as a cathode 29.

[0100] The above describes only a typical structure and fabrication method of an organic electroluminescent device. It should be understood that the present invention is not limited to this structure. The charge generation layer material or electron transport layer material of the present invention can be used in organic electroluminescent devices of any structure, and the organic electroluminescent device can be fabricated using any fabrication method known in the art.

[0101] A third aspect of the present invention provides a display device comprising the organic electroluminescent device provided in the second aspect of the present invention. The display device includes, but is not limited to, a monitor, a television, a tablet computer, a mobile communication terminal, etc.

[0102] The synthesis method of the compounds of the present invention 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 compounds of the present invention.

[0103] Synthesis example

[0104] Synthesis of compound A1:

[0105]

[0106] 100 mmol of 2-naphthoboric acid, 100 mmol of p-chlorobromobenzene, 41.4 g of potassium carbonate (300 mmol), 800 mL of toluene, and 200 mL of water were added to a reaction flask, along with 1 mol% of tetra(triphenylphosphine)palladium (Pd(PPh3)4). The reaction was carried out at 80 °C for 12 h. After the reaction was completed, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder M1. The amount of Pd(PPh3)4 added was 1 mol% of 2-naphthoboric acid.

[0107] 100 mmol of M1, 100 mmol of pinacol diborate, 41.4 g of potassium carbonate (300 mmol), and 800 mL of dioxane were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 100 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M2. The amount of Pd(PPh3)4 added was 1 mol% of M1.

[0108] 100 mmol of 2,9-dichloro-1,10-phenanthroline, 100 mmol of M2, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M3. The amount of Pd(PPh3)4 added was 1 mol% of 2,9-dichloro-1,10-phenanthroline.

[0109] 100 mmol of 3,5-dicyanobromobenzene, 100 mmol of p-chlorophenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of toluene, and 200 mL of water were added to a reaction flask, along with 1 mol% of tetra(triphenylphosphine)palladium (Pd(PPh3)4). The reaction was carried out at 80 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M4. The amount of Pd(PPh3)4 added was 1 mol% of 3,5-dicyanobromobenzene.

[0110] 100 mmol of M4, 100 mmol of pinacol diborate, 41.4 g of potassium carbonate (300 mmol), and 800 mL of dioxane were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 100 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M5. The amount of Pd(PPh3)4 added was 1 mol% of M4.

[0111] 100 mmol of M3, 100 mmol of M5, 41.4 g of potassium carbonate (300 mmol), 800 mL of tetrahydrofuran (THF), and 200 mL of water were added to a reaction flask, along with 1 mol% of tetra(triphenylphosphine)palladium (Pd(PPh3)4). The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, Al. The amount of Pd(PPh3)4 added was 1 mol% of M3.

[0112] 1 H NMR (400MHz, Chloroform) δ8.72(d,J=8.0Hz,4H),8.40(d,J=7.6Hz,2H),8.32(s,2H),8.08(t,J=7.6Hz,3H),8.00(d,J=7 .2Hz,1H),7.86(d,J=7.2Hz,1H),7.82(d,J=7.6Hz,4H),7.68-7.54(m,4H),7.36(d,J=7.2Hz,1H),7.30(d,J=8.0Hz,2H).

[0113] Synthesis of compound A6:

[0114]

[0115] 100 mmol of 2-bromo-5-chloropyridine, 100 mmol of phenylboronic acid, 41.4 g of potassium carbonate (300 mmol), and 800 mL of toluene were added to a reaction flask, along with 1 mol% of tetra(triphenylphosphine)palladium (Pd(PPh3)4). The reaction was carried out at 80 °C for 12 h. After the reaction was completed, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder M1. The amount of Pd(PPh3)4 added was 1 mol% of p-chlorobromobenzene.

[0116] 100 mmol of M1, 100 mmol of pinacol diborate, 41.4 g of potassium carbonate (300 mmol), and 800 mL of dioxane were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 100 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M2. The amount of Pd(PPh3)4 added was 1 mol% of M1.

[0117] 100 mmol of p-chlorobromobenzene, 100 mmol of M2, 41.4 g of potassium carbonate (300 mmol), 800 mL of tetrahydrofuran (THF), and 200 mL of water were added to a reaction flask, along with 1 mol% of tetra(triphenylphosphine)palladium (Pd(PPh3)4). The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M3. The amount of Pd(PPh3)4 added was 1 mol% of the p-chlorobromobenzene.

[0118] 100 mmol of M3, 100 mmol of pinacol diborate, 41.4 g of potassium carbonate (300 mmol), and 800 mL of dioxane were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 100 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M4. The amount of Pd(PPh3)4 added was 1 mol% of M3.

[0119] 100 mmol of 2,9-dichloro-1,10-phenanthroline, 100 mmol of M4, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M5. The amount of Pd(PPh3)4 added was 1 mol% of 2,9-dichloro-1,10-phenanthroline.

[0120] 100 mmol of 3,5-dicyanobromobenzene, 100 mmol of pinacol diborate, 41.4 g of potassium carbonate (300 mmol), and 800 mL of dioxane were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 100 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M6. The amount of Pd(PPh3)4 added was 1 mol% of 3,5-dicyanobromobenzene.

[0121] 100 mmol of M5, 100 mmol of M6, 41.4 g of potassium carbonate (300 mmol), 800 mL of tetrahydrofuran (THF), and 200 mL of water were added to a reaction flask, along with 1 mol% of tetra(triphenylphosphine)palladium (Pd(PPh3)4). The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder A6. The amount of Pd(PPh3)4 added was 1 mol% of M5.

[0122] 1 H NMR(400MHz,Chloroform)δ8.93(s,1H),8.75(s,2H),8.72(d,J=7.6Hz,2H),8.40(d,J=7.2Hz,2H),8.34(d,J=7.2Hz,2H),8.10(s,1H) ,8.00(d,J=8.0Hz,1H),7.92(d,J=6.8Hz,1H),7.88(d,J=6.8Hz,1H),7.60-7.48(m,4H),7.36(d,J=8.0Hz,2H),7.26(d,J=8.0Hz,2H).

[0123] Synthesis of compound A10:

[0124]

[0125] 100 mmol of p-chlorobromobenzene, 100 mmol of diphenylphosphine oxide, 41.4 g of potassium carbonate (300 mmol), and 800 mL of toluene were added to a reaction flask, along with 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4). The reaction was carried out at 80 °C for 12 h. After the reaction was completed, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder M1. The amount of Pd(PPh3)4 added was 1 mol% of the p-chlorobromobenzene.

[0126] 100 mmol of M1, 100 mmol of pinacol diborate, 41.4 g of potassium carbonate (300 mmol), and 800 mL of dioxane were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 100 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M2. The amount of Pd(PPh3)4 added was 1 mol% of M1.

[0127] 100 mmol of 2,9-dichloro-1,10-phenanthroline, 100 mmol of 4-(triphenylsilyl)phenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder M3. The amount of Pd(PPh3)4 added was 1 mol% of 2,9-dichloro-1,10-phenanthroline.

[0128] 100 mmol of 3,5-dicyanobromobenzene, 100 mmol of pinacol diborate, 41.4 g of potassium carbonate (300 mmol), and 800 mL of dioxane were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 100 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M4. The amount of Pd(PPh3)4 added was 1 mol% of 3,5-dicyanobromobenzene.

[0129] 100 mmol of M4, 100 mmol of 4-bromo-4'-bromo-biphenyl, 41.4 g of potassium carbonate (300 mmol), 800 mL of toluene, and 200 mL of water were added to a reaction flask. 1 mol% of tetra(triphenylphosphine)palladium (Pd(PPh3)4) was also added, and the mixture was reacted at 80 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M5. The amount of Pd(PPh3)4 added was 1 mol% of M4.

[0130] 100 mmol of M5, 100 mmol of pinacol diborate, 41.4 g of potassium carbonate (300 mmol), and 800 mL of dioxane were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 100 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M6. The amount of Pd(PPh3)4 added was 1 mol% of M5.

[0131] 100 mmol of M3, 100 mmol of M6, 41.4 g of potassium carbonate (300 mmol), 800 mL of tetrahydrofuran (THF), and 200 mL of water were added to a reaction flask, along with 1 mol% of tetra(triphenylphosphine)palladium (Pd(PPh3)4). The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, Al0. The amount of Pd(PPh3)4 added was 1 mol% of M3.

[0132] 1 H NMR (400MHz, Chloroform) δ8.70(d,J=8.0Hz,2H),8.38(d,J=7.6Hz,2H),8.32(d,J=7.6Hz,2H),8.28(s,2H),8.07(s,1H),7.98(d,J=8.0 Hz,2H),7.86(t,J=7.6Hz,3H),7.82-7.75(m,4H),7.58(d,J=7.2Hz,1H),7.55-7.46(m,6H),7.34(d,J=8.0Hz,2H),7.26(d,J=8.0Hz,4H).

[0133] Synthesis of compound A24:

[0134]

[0135] 100 mmol of 2-chloro-4,6-diphenylpyrimidine, 100 mmol of p-chlorophenylboronic acid, 41.4 g of potassium carbonate (300 mmol), and 800 mL of toluene were added to a reaction flask, along with 1 mol% of tetra(triphenylphosphine)palladium (Pd(PPh3)4). The reaction was carried out at 80 °C for 12 h. After the reaction was completed, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder M1. The amount of Pd(PPh3)4 added was 1 mol% of 2-chloro-4,6-diphenylpyrimidine.

[0136] 100 mmol of M1, 100 mmol of pinacol diborate, 41.4 g of potassium carbonate (300 mmol), and 800 mL of dioxane were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 100 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M2. The amount of Pd(PPh3)4 added was 1 mol% of M1.

[0137] 100 mmol of 2,9-dichloro-1,10-phenanthroline, 100 mmol of M2, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M3. The amount of Pd(PPh3)4 added was 1 mol% of 2,9-dichloro-1,10-phenanthroline.

[0138] 100 mmol of 2,4,6-tricyanobromobenzene, 100 mmol of pinacol diborate, 41.4 g of potassium carbonate (300 mmol), and 800 mL of dioxane were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 100 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M4. The amount of Pd(PPh3)4 added was 1 mol% of 2,4,6-tricyanobromobenzene.

[0139] 100 mmol of M3, 100 mmol of M4, 41.4 g of potassium carbonate (300 mmol), 800 mL of tetrahydrofuran (THF), and 200 mL of water were added to a reaction flask, along with 1 mol% of tetra(triphenylphosphine)palladium (Pd(PPh3)4). The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, A24. The amount of Pd(PPh3)4 added was 1 mol% of M3.

[0140] 1 H NMR(400MHz,Chloroform)δ8.70(d,J=8.0Hz,2H),8.48(s,2H),8.38(d,J=7.6Hz,2H),8.23 (s,1H),8.00-7.93(m,6H),7.88(d,J=7.2Hz,1H),7.60-7.42(m,7H),7.32(d,J=8.0Hz,2H).

[0141] Synthesis of compound A36:

[0142]

[0143] 100 mmol of 3,5-dicyanobromobenzene, 100 mmol of pinacol diborate, 41.4 g of potassium carbonate (300 mmol), and 800 mL of dioxane were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 100 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder M1. The amount of Pd(PPh3)4 added was 1 mol% of 3,5-dicyanobromobenzene.

[0144] 100 mmol of M1, 100 mmol of 2-bromo-5-chloropyridine, 41.4 g of potassium carbonate (300 mmol), 800 mL of toluene, and 200 mL of water were added to a reaction flask, along with 1 mol% of tetra(triphenylphosphine)palladium (Pd(PPh3)4). The reaction was carried out at 80 °C for 12 h. After the reaction was completed, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M2. The amount of Pd(PPh3)4 added was 1 mol% of M1.

[0145] 100 mmol of M2, 100 mmol of pinacol diborate, 41.4 g of potassium carbonate (300 mmol), and 800 mL of dioxane were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 100 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M3. The amount of Pd(PPh3)4 added was 1 mol% of M2.

[0146] 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 to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M4. The amount of Pd(PPh3)4 added was 1 mol% of 2,9-dichloro-1,10-phenanthroline.

[0147] 100 mmol of 3,5-dibromochlorobenzene, 200 mmol of pyridine-3-boric acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of toluene, and 200 mL of water were added to a reaction flask. 2 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) was also added, and the mixture was reacted at 80 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder M5. The amount of Pd(PPh3)4 added was 2 mol% of 3,5-dibromochlorobenzene.

[0148] 100 mmol of M5, 100 mmol of pinacol diborate, 41.4 g of potassium carbonate (300 mmol), and 800 mL of dioxane were added to a reaction flask, along with 1 mol% of Pd(PPh3)4. The reaction was carried out at 100 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, M6. The amount of Pd(PPh3)4 added was 1 mol% of M5.

[0149] 100 mmol of M4, 100 mmol of M6, 41.4 g of potassium carbonate (300 mmol), 800 mL of tetrahydrofuran (THF), and 200 mL of water were added to a reaction flask, along with 1 mol% of tetra(triphenylphosphine)palladium (Pd(PPh3)4). The reaction was carried out at 60 °C for 12 h. After the reaction was complete, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, the mixture was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to obtain a white powder, A36. The amount of Pd(PPh3)4 added was 1 mol% of M4.

[0150] 1 H NMR(400MHz,Chloroform)δ9.28(s,1H),9.23(s,2H),8.75(s,2H),8.70(d,J=7.2H z,2H),8.64(s,2H),8.46(d,J=6.8Hz,1H),8.40(d,J=6.8Hz,1H),8.30(d,J=7.6Hz, 3H),8.20(s,1H),8.08(s,1H),8.03(d,J=8.0Hz,1H),7.82(d,J=8.0Hz,1H),7.68(d ,J=7.6Hz,1H),7.62(d,J=7.2Hz,1H),7.48(t,J=7.6Hz,2H),7.32(d,J=8.0Hz,1H).

[0151] Other compounds of the present invention can be synthesized by selecting suitable raw materials according to the above synthesis examples, or by selecting any other suitable method and raw materials.

[0152] Example 1

[0153] The glass substrate 1 coated with a 150nm thick ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone-ethanol mixed solvent, baked in a clean environment until all moisture was removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam to obtain a glass substrate 21 with a reflective anode 22.

[0154] Then, the glass substrate 21 with the reflective anode 22 is placed in a vacuum chamber and evacuated to a vacuum level of less than 10. -5A first hole injection layer 231 is vacuum-deposited on the anode layer film of the glass substrate 21 of the aforementioned reflective anode 22. The material of the first hole injection layer 231 includes hole injection layer material HT-11 and p-type dopant p-1. The deposition is performed using a multi-source co-evaporation method. The deposition rate of hole injection layer material HT-11 is adjusted to 0.1 nm / s, and the deposition rate of p-type dopant p-1 is 3% of the deposition rate of hole injection layer material HT-11. The total film thickness is 10 nm. The hole injection layer material HT-11 and p-type dopant p-1 are as follows:

[0155]

[0156] Then, a hole transport layer material HT-11 is vacuum-deposited on the first hole injection layer 231 as the first hole transport layer 241, wherein the deposition rate is 0.1 nm / s and the deposition film thickness is 80 nm.

[0157] Then, a first light-emitting layer 251 is vacuum-deposited on the first hole transport layer 241. The first light-emitting layer 251 includes a host material BH-2 and a guest material BD-1. The deposition is performed using a multi-source co-evaporation method. The deposition rate of the host material BH-2 is adjusted to 0.1 nm / s, and the deposition rate of the guest material BD-1 is 3% of the deposition rate of the host material BH-2. The deposition film thickness is 30 nm. The host material BH-2 and the guest material BD-1 are as follows:

[0158]

[0159] Then, a first electron transport layer 261 is vacuum-deposited on the first light-emitting layer 251. The materials of the first electron transport layer 261 are compound ET30 and LiQ, wherein the deposition rate of compound ET30 is 0.1 nm / s, the deposition rate ratio of compound ET30 to LiQ is 7:3, and the total deposition film thickness is 30 nm; the compounds ET30 and LiQ are as follows:

[0160]

[0161] The first hole injection layer 231, the first hole transport layer 241, the first light-emitting layer 251 and the first electron transport layer 261 together constitute the first light-emitting unit;

[0162] On the uppermost first electron transport layer 261 of the first light-emitting unit, the compound Al provided by the present invention and ytterbium (Yb) are vapor-deposited as a charge generation layer 27, wherein the vapor deposition rate of compound Al is 0.01 nm / s, the vapor deposition rate ratio of compound Al to Yb is 98:2, and the total vapor deposition film thickness is 10 nm.

[0163] A second hole injection layer 232 is deposited on the charge generation layer 27. The material of the second hole injection layer 232 includes hole injection layer material HT-11 and p-type dopant p-1. The evaporation rate of hole injection layer material HT-11 is adjusted to 0.1 nm / s, the ratio of the evaporation rates of hole injection layer material HT-11 and p-type dopant p-1 is 97:3, and the total evaporation film thickness is 10 nm.

[0164] Then, a hole transport layer material HT-11 is vacuum-deposited on the second hole injection layer 232 as the second hole transport layer 242, wherein the deposition rate is 0.1 nm / s and the deposition film thickness is 80 nm.

[0165] Then, a second light-emitting layer 252 is vacuum-deposited on the second hole transport layer 242. The second light-emitting layer includes a light-emitting layer host material BH-2 and a light-emitting layer guest material BD-1. The deposition is performed using a multi-source co-evaporation method. The deposition rate of the light-emitting layer host material BH-2 is adjusted to 0.1 nm / s, the deposition rate of the light-emitting layer guest material BD-1 is 3% of the deposition rate of the light-emitting layer host material BH-2, and the total deposition film thickness is 30 nm.

[0166] Then, a second electron transport layer 262 is vacuum-deposited on the second light-emitting layer 252. The electron transport materials are compound ET30 and LiQ, wherein the deposition rate of compound ET30 is 0.1 nm / s, the deposition rate ratio of compound ET30 to LiQ is 7:3, and the total deposition film thickness is 30 nm.

[0167] The second hole injection layer 232, the second hole transport layer 242, the second light-emitting layer 252, and the second electron transport layer 262 together constitute the second light-emitting unit;

[0168] Then, a LiF layer with a thickness of 0.5 nm is vacuum-deposited on the uppermost second electron transport layer 262 of the second light-emitting unit as an electron injection layer 28, wherein the deposition rate is 0.1 nm / s;

[0169] Finally, an Al layer with a thickness of 150 nm is vacuum-deposited on the electron injection layer 28 as the cathode electrode 29 of the organic electroluminescent device, wherein the deposition rate is 0.1 nm / s.

[0170] Examples 2-5

[0171] Except for replacing A1 with A6, A10, A24, and A36 respectively for the charge generation layer material, the rest is the same as in Example 1.

[0172] Comparative Example 1

[0173] Except for the use of CGL00R1 instead of A1 as the charge generation layer material, the rest is the same as in Example 1;

[0174]

[0175] Comparative Example 2

[0176] Except for the use of CGL00R5 instead of Al for the charge generation layer material, the rest is the same as in Example 1;

[0177]

[0178] Comparative Example 3

[0179] Except for the use of R instead of Al in the charge generation layer material, the rest is the same as in Example 1;

[0180]

[0181] The organic electroluminescent devices prepared by the above process were subjected to the following performance measurements:

[0182] Under the same brightness, the driving voltage, current efficiency, and lifetime of the organic electroluminescent devices prepared in Examples 1 to 5 and Comparative Examples 1 to 3 were measured using a digital source meter and a luminance meter. Specifically, the voltage was increased at a rate of 0.1V per second, and the measurement was performed when the brightness of the organic electroluminescent device reached 1000 cd / m². 2 The voltage at that time is the driving voltage, and the current density at that time is measured simultaneously; the ratio of brightness to current density is the current efficiency; the life test of LT95 is as follows: using a luminance meter at 1000 cd / m² 2 At a constant current, the brightness of the organic electroluminescent device decreased to 950 cd / m² under the specified brightness. 2 The time is expressed in hours. The results are shown in Table 1.

[0183] Table 1. Performance results of organic electroluminescent devices

[0184]

[0185]

[0186] As shown in Table 1, the organic electroluminescent devices prepared in Examples 1 to 5 use compounds A1, A6, A10, A24, and A36 provided by this invention as the first charge generation layer material. Compared with Comparative Examples 1, 2, and 3, which use known materials in the prior art as the charge generation layer material of the organic electroluminescent devices, the organic electroluminescent devices of this invention have lower driving voltage, higher current efficiency, and longer LT95 lifetime. This demonstrates that when the compounds of formula (I) are used as charge generation materials in organic electroluminescent devices, this invention can effectively reduce the driving voltage, improve current efficiency, and extend the device's lifespan. The materials of this invention, in particular, show significant performance improvements in improving the efficiency and extending the lifespan of organic electroluminescent devices, resulting in high-performance organic electroluminescent devices.

[0187] The above description is merely a preferred embodiment of the present invention and is not intended to limit the scope of protection of the present invention. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention are included within the scope of protection of the present invention.

Claims

1. A phenanthroline compound comprising a cyano-substituted group, characterized in that, It has a structure as shown in equation (I): Ar1 is selected from unsubstituted or Rc-substituted C6-C. 30 Aryl, unsubstituted or Rc-substituted C3-C 30 Mixed aromatics; L1 and L2 are each independently selected from chemical bonds, and are either unsubstituted or Rc-substituted C6-C bonds. 30 aryl, unsubstituted or Rc-substituted C3-C 30 heteroaryl; A is selected from the following excerpt: The heteroatoms on the heteroaryl group or the heteroalkylene group are each independently selected from O, S or N; The substituents Rc of each group are independently selected from hydrogen, deuterium, halogen, nitro, cyano, C1-C4 alkyl, phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl, or naphthyl.

2. The cyano-substituted phenanthroline compound according to claim 1, characterized in that, Ar1 is selected from the following groups of compounds that are unsubstituted or Rc-substituted: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, fluoranthene, anthracene, dibenzofuran, dibenzothiophene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, spirofluorene, pyridine, quinoline, quinazoline, pyrimidine, triazine, phenanthrene, carbazole, and phosphoxy.

3. The cyano-substituted phenanthroline compound according to claim 1, characterized in that, L1 and L2 are independently chemically bonded, unsubstituted or Rc-substituted groups of the following compounds: phenyl, pyridinyl, pyrimidinyl, quinoxalinyl, quinazolinyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, fluorenyl, anthraceneyl, dibenzofuranyl, dibenzothiopheneyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl.

4. The cyano-substituted phenanthroline compound according to claim 1, characterized in that, The compounds are selected from those shown in A1 to A40 below:

5. An organic electroluminescent device, characterized in that, It includes a charge-generating layer, wherein the charge-generating layer material comprises at least one of the cyano-substituted phenanthroline compounds according to any one of claims 1 to 4.

6. The organic electroluminescent device according to claim 5, characterized in that, The charge-generating layer material includes metallic Li or Yb, and the mass percentage of metallic Li or Yb is 0.5%-15% based on the mass of the charge-generating layer material.

7. The organic electroluminescent device according to claim 5, characterized in that, The thickness of the charge generation layer is 10nm-30nm.

8. A display device, characterized in that, An organic electroluminescent device comprising any one of claims 5-7.

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