Silicon-based substituted phenanthroline compound, organic electroluminescent device and display device

Abstract

The invention belongs to the technical field of organic light-emitting display, and particularly relates to a silicon-based substituted phenanthroline compound, an organic light-emitting device and a display device. The structure of the compound is shown as a formula (I). The organic light-emitting device provided by the invention comprises the charge generation layer and the electron transport layer, the charge generation layer is made of the silicon-substituted phenanthroline compound, has efficient charge generation capability, can effectively improve the light-emitting efficiency of the organic light-emitting device, and has a relatively shallow energy level, so that the light-emitting efficiency of the organic light-emitting device is improved. The organic electroluminescent device can be better matched with an adjacent layer material for use, the charge transmission performance 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. # imgabs0 #

Description

Technical Field

[0001] The present invention belongs to the technical field of organic light-emitting display, and particularly relates to a silicon-based substituted phenanthroline compound, an organic electroluminescent device, and a display device. Background Art

[0002] Electroluminescence (EL) refers to the phenomenon that a luminescent material emits light under the action of an electric field, being excited by current and voltage. It is a luminescence process that directly converts electrical energy into light energy. Organic electroluminescent displays (hereinafter referred to as OLEDs) have a series of advantages such as self-luminescence, low-voltage DC drive, all-solid state, wide viewing angle, light weight, simple composition and process. Compared with liquid crystal displays, organic electroluminescent displays do not require a backlight, have a large viewing angle, low power, a response speed that can reach 1000 times that of liquid crystal displays, and a manufacturing cost lower than that of liquid crystal displays with the same resolution. Therefore, organic electroluminescent devices have very broad application prospects.

[0003] With the continuous advancement of OLED technology in the two major fields of lighting and display, people pay more attention to the research on high-efficiency organic materials that affect the performance of OLED devices. A highly efficient and long-life organic electroluminescent device is usually the result of an optimized combination of the device structure and various organic materials, which poses great opportunities and challenges for chemists to design and develop functional materials with various structures. Stacked devices can effectively improve the working life of the device, so they have been a research hotspot in recent years. How to develop high-performance charge generation layer materials and select matching light-emitting units to improve the light-emitting efficiency of organic electroluminescent devices and extend their service life has become a technical problem that needs to be solved urgently by those skilled in the art. Summary of the Invention

[0004] The purpose of the present invention is to provide a silicon-based substituted phenanthroline compound, an organic electroluminescent device, and a display device to improve the light-emitting efficiency of the organic electroluminescent device and extend its service life.

[0005] The purpose of the first aspect of the present invention is to provide a silicon-based substituted phenanthroline compound, the structure of which is shown in formula (I):

[0006]

[0007] Wherein,

[0008] R 1 -R 6 Each independently selected from C1-C3 alkanes, C6-C30 aryls that are unsubstituted or substituted by Rc, and C3-C30 heteroaryls that are unsubstituted or substituted by Rc;

[0009] L1 and L 2 are each independently selected from a chemical bond, an unsubstituted or Rc-substituted C6-C30 arylene group, and an unsubstituted or Rc-substituted C3-C30 heteroarylene group, and L 1 and L 2 are not simultaneously a chemical bond;

[0010] m and n are each independently selected from 0 and 1, and m + n ≥ 1;

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

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

[0013] Preferably, the R 1 -R 6 are each independently selected from C1-C3 alkanes, unsubstituted or Rc-substituted C6-C18 aryl groups, and unsubstituted or Rc-substituted C3-C18 heteroaryl groups; and / or,

[0014] the L 1 and L 2 are each independently selected from a chemical bond, an unsubstituted or Rc-substituted C6-C18 arylene group, and an unsubstituted or Rc-substituted C3-C30 heteroarylene group.

[0015] More preferably, the R 1 -R 6 are each independently selected from methyl, ethyl, isopropyl, and groups of the following compounds that are unsubstituted or substituted with Rc: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, dibenzofuran, dibenzothiophene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, spirofluorene.

[0016] More preferably, the L 1 and L 2 are each independently selected from a chemical bond, and groups of the following compounds that are unsubstituted or substituted with Rc: phenyl, pyridyl, pyrimidinyl, quinoxalinyl, quinazolinyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylenyl, fluorenyl, anthryl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl.

[0017] Preferably, the compound of formula (I) is selected from the compounds shown as A1 to A35 below:

[0018]

[0019]

[0020] Another object of the present invention is to provide an organic electroluminescent device, which includes a charge generation layer and an electron transport layer, and the charge generation layer material includes the compound of formula (I).

[0021] Preferably, the charge generation layer material includes metal Li or Yb, and based on the mass of the charge generation layer material, the mass percentage content of the metal Li or Yb is 0.5%-2.5%.

[0022] Preferably, the thickness of the charge generation layer is 10 nm - 30 nm, and the thickness of the electron transport layer is 10 nm - 40 nm.

[0023] Preferably, the electron transport layer material includes LiQ, and based on the mass of the electron transport layer material, the mass percentage content of LiQ is 30%-70%.

[0024] Another object of the present invention is to provide a display device, which includes the above-mentioned organic electroluminescent device.

[0025] Compared with the prior art, the beneficial effects of the present invention are as follows:

[0026] The organic electroluminescent device provided by the present invention, the silicon-based substituted phenanthroline compound, has high-efficient charge generation ability, can effectively improve the luminous efficiency of the organic electroluminescent device, and at the same time has a relatively shallow energy level and can be used in combination with the materials of adjacent layers, can effectively improve the charge transport performance of the organic electroluminescent device, improve the luminous efficiency of the organic electroluminescent device, reduce its driving voltage and extend its service life. The display device provided by the present invention has excellent display effects.

[0027] Of course, it is not necessary for any product or method of implementing the present invention to achieve all the above-mentioned advantages simultaneously. BRIEF DESCRIPTION OF THE DRAWINGS

[0028] In order to more clearly illustrate the technical solutions in the present invention, the following will briefly introduce the drawings required for the description of the embodiments. Obviously, the following drawings are only some embodiments of the present invention, and those of ordinary skill in the art can also obtain other embodiments based on these drawings.

[0029] Figure 1It is a schematic structural diagram of a typical organic electroluminescent device 20. Each part is respectively: 21, a substrate; 22, a reflective anode; 231, a first hole injection layer; 241, a first hole transport layer; 251, a first light-emitting layer; 261, a first electron transport layer; 27, a charge generation layer; 232, a second hole injection layer; 242, a second hole transport layer; 252, a second light-emitting layer; 262, a second electron transport layer; 28, an electron injection layer; 29, a cathode electrode. Detailed implementation manners

[0030] Next, the technical solutions in the present invention will be clearly and completely described in conjunction with the accompanying drawings in the present invention. Obviously, the described embodiments are only a part of the embodiments of the present invention, rather than all the embodiments. All other embodiments obtained by those of ordinary skill in the art based on the present invention belong to the scope of protection of the present invention.

[0031] In the present invention, there are no particular limitations on the types and structures of organic electroluminescent devices, and they can be organic electroluminescent devices of different types and structures well-known in the art, as long as at least one of the charge generation layer materials and at least one of the electron transport materials provided by the present invention can be used.

[0032] In one embodiment of the present invention, an organic electroluminescent device includes an anode and a cathode, and m light-emitting units and m - 1 charge generation layers are stacked between the anode and the cathode. The charge generation layers are between two adjacent light-emitting units. Each charge generation layer includes an n-type charge generation layer and a p-type charge generation layer, where m is an integer greater than or equal to 2; each light-emitting unit includes at least one light-emitting layer, and the maximum emission wavelengths of the light emitted in different light-emitting units are different; at least one of the n-type charge generation layers includes at least one compound represented by formula (I) and a metal-containing material, and the metal-containing material includes a metal, a metal complex, or a combination thereof;

[0033] In one embodiment of the present invention, the light-emitting units in the organic electroluminescent device may include a first light-emitting unit and a second light-emitting unit, and the two light-emitting units may be the same or different; the charge generation layer 27 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 generation layer, the second light-emitting unit may be disposed between the charge generation layer and the cathode, and the n-type charge generation layer of the charge generation layer may include at least one compound represented by formula (I) and a metal-containing material.

[0034] In other embodiments of the present invention, the organic electroluminescent device of the present invention may be a top-emitting structure light-emitting device, and may sequentially include 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.

[0035] The organic electroluminescent device of the present invention may also be a bottom-emitting structure light-emitting device, which may sequentially 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 on a substrate.

[0036] The organic electroluminescent device of the present invention may also be a double-sided light-emitting structure light-emitting device, which may sequentially 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 transparent or semi-transparent cathode on a substrate.

[0037] 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.

[0038] In addition, for the organic electroluminescent device of the present invention, an electron blocking layer may be provided between the hole transport layer and the light-emitting layer, a hole blocking layer may be provided between the light-emitting layer and the electron transport layer, and a light extraction layer may be provided on the transparent electrode on the light-emitting side. However, the structure of the organic electroluminescent device of the present invention is not limited to the above specific structure, and if necessary, the above layers may be omitted or added. The present invention has no particular limitation on the thickness of the above 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 object of the present invention can be achieved. For example, the organic electroluminescent device may sequentially include an anode (100 nm to 150 nm) made of 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, and a light extraction layer (50 nm to 90 nm) on a substrate. Exemplarily, Figure 1 FIG. shows a schematic diagram of a typical organic electroluminescent device 20, 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 thatFigure 1 The structure of a typical organic electroluminescent device is only schematically shown, and 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 any type of organic electroluminescent device.

[0039] In some embodiments of the present invention, the charge generation layer material includes metal Li or Yb, and based on the mass of the charge generation layer material, the mass percentage content of the metal Li or Yb is 0.5% - 2.5%.

[0040] In some embodiments of the present invention, the electron transport layer material includes LiQ, and based on the mass of the electron transport layer material, the mass percentage content of the LiQ is 30% - 70%.

[0041] For convenience, the organic electroluminescent device of the present invention will be described below, but this does not mean any limitation to the protection scope of the present invention. It can be understood that all organic electroluminescent devices using the charge generation layer material or electron transport layer material of the present invention are within the protection scope of the present invention.

[0042] In the present invention, there is no particular limitation on the substrate 21, and conventional substrates used in organic electroluminescent devices in the prior art can be used, for example, glass, polymer materials, and glass and polymer materials with thin film transistor (TFT) components, etc.

[0043] In the present invention, there is no particular limitation on the material of the reflective anode 22, and 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), zinc oxide (ZnO), etc., or can be selected from metal materials such as silver and its alloys, aluminum and its alloys, etc., or can also be selected from organic conductive materials such as poly(3,4-ethylenedioxythiophene) (PEDOT), etc., or the reflective anode 22 is a multilayer structure formed by the above materials. The present invention has no particular limitation on the number of layers of the multilayer structure, and it can be selected according to actual needs as long as it can meet the purpose of the present invention. For example, 1 layer, 2 layers, 3 layers or more layers.

[0044] In the present invention, there is no particular limitation on the materials of the first hole injection layer 231 and the second hole injection layer 232, and they can be made of hole injection layer materials well-known in the art or made of hole transport layer materials (HTM) well-known in the art. For example, at least one of the known hole transport layer materials (HTM) is selected as the hole injection layer material.

[0045] In the present invention, the first hole injection layer 231 and the second hole injection layer 232 may further include a p-type dopant. There is no particular limitation on the type of the p-type dopant in the present invention, and various p-type dopants known in the art can be used. For example, the p-type dopant may be selected from, but not limited to, at least one of the following compounds p-1 to p-3:

[0046]

[0047] In the present invention, there is no particular limitation on the amount of the p-type dopant, and the amount can be the amount known to those skilled in the art.

[0048] In the present invention, there is no particular limitation 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. There is no particular limitation on the number of layers of the hole transport layer in the present invention, and it can be adjusted according to actual needs as long as the purpose of the present invention can be satisfied. For example, 1 layer, 2 layers, 3 layers, 4 layers or more layers.

[0049] For example, the HTM for the hole injection layer material and the HTM for the hole transport layer material may be selected from, but not limited to, at least one of the following compounds HT-1 to HT-31:

[0050]

[0051]

[0052] In the present invention, there is no particular limitation on the materials of the first light-emitting layer 251 and the second light-emitting layer 252. They may each contain a light-emitting layer host material and a light-emitting layer guest material. Among them, there is no particular limitation on the amounts of the light-emitting layer host material and the light-emitting layer guest material, and the amounts can be the amounts known to those skilled in the art.

[0053] In the present invention, the light-emitting layer may include a blue light-emitting layer, a green light-emitting layer or a red light-emitting layer. There is no particular limitation 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.

[0054] In the present invention, there is no particular limitation on the light-emitting layer host material, and at least one of the light-emitting layer host materials known in the art can be used. For example, it may be selected from, but not limited to, at least one of the following compounds BH-1 to BH-10:

[0055]

[0056] In the present invention, there is no particular limitation 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, the host material of the light-emitting layer can be selected from, but not limited to, at least one of the following compounds BD-1 to BD-9:

[0057]

[0058] In the present invention, the above-mentioned first electron transport layer 261 and second electron transport layer 262 contain at least one of the electron transport layer materials of the present invention, and can also contain a combination of at least one of the electron transport layer materials of the present invention and at least one of the known electron transport materials. There is no particular limitation on the number of layers of the electron transport layer, and it can be adjusted according to actual needs as long as the object of the present invention can be satisfied. For example, 1 layer, 2 layers, 3 layers, 4 layers or more layers.

[0059] For example, the known electron transport materials can be selected from, but not limited to, at least one of the following compounds ET-1 to ET-57:

[0060]

[0061]

[0062]

[0063]

[0064] In the present invention, the first electron transport layer 261 and the second electron transport layer 262 can each further include an n-type dopant. There is no particular limitation on the type of the 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:

[0065]

[0066] In the present invention, there is no particular limitation on the amount of the n-type dopant, and the amount known to those skilled in the art can be used.

[0067] In the present invention, the charge generation layer 27 can contain at least one of the charge generation layer materials of the present invention, and can also contain a combination of at least one of the charge generation layer materials of the present invention and at least one of the known charge generation materials.

[0068] For example, the known charge generation materials can be selected from, but not limited to, at least one of the following compounds CGL00R1 to CGL00R5:

[0069]

[0070] In the present invention, there is no particular limitation on the material of the above-mentioned electron injection layer 28, and known electron injection layer materials in the art can be used. For example, it may include but is not limited to at least one of materials such as lithium 8-hydroxyquinoline (LiQ), LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, etc. in the prior art.

[0071] In the present invention, there is no particular limitation on the material of the cathode electrode 29, and it can be selected from but is not limited to metals, metal mixtures, oxides such as magnesium-silver mixture, LiF / Al, ITO, Al, etc.

[0072] There is no particular limitation on the method for preparing the organic electroluminescent device of the present invention, and any method known in the art can be adopted. For example, the present invention can be prepared by the following preparation method:

[0073] The method for preparing the organic electroluminescent device of the present invention may further include but is not limited to the following steps:

[0074] (1) Clean the reflective anode 22 on the top-emitting organic electroluminescent device substrate 21, and in the cleaning machine, respectively perform steps such as chemical cleaning, water washing, brushing, high-pressure water washing, air knife, etc., and then perform heat treatment;

[0075] (2) Vacuum deposit a hole injection material on the reflective anode 22 as the first hole injection layer 231;

[0076] (3) Vacuum deposit a hole transport layer material on the first hole injection layer 231 as the first hole transport layer 241;

[0077] (4) Vacuum deposit the first light-emitting layer 251 on the first hole transport layer 241, and the light-emitting layer contains a light-emitting layer host material and a light-emitting layer guest material;

[0078] (5) Vacuum deposit an electron transport material on the first light-emitting layer 251 as the first electron transport layer 261;

[0079] (6) Vacuum deposit a charge generation material on the first electron transport layer 261 as the charge generation layer 27;

[0080] (7) Vacuum deposit a hole injection material on the charge generation layer 27 as the second hole injection layer 232;

[0081] (8) Vacuum deposit a hole transport layer material on the second hole injection layer 232 as the second hole transport layer 242;

[0082] (9) Vacuum deposit the second light-emitting layer 252 on the second hole transport layer 242, and the light-emitting layer contains a light-emitting layer host material and a light-emitting layer guest material;

[0083] (10) A hole injection layer 252 is formed by vacuum evaporation of a hole injection material on the second light-emitting layer 262;

[0084] (11) An electron injection layer 28 is formed by vacuum evaporation of an electron injection material on the second electron transport layer 262;

[0085] (12) A cathode 29 is formed by vacuum evaporation of a cathode material on the electron injection layer 28.

[0086] The above only describes the structure and preparation method of a typical 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 any structure of organic electroluminescent devices, and any preparation method known in the art can be used to prepare the organic electroluminescent devices.

[0087] The present invention also provides a display device, which includes the above organic electroluminescent device of the present invention. The display device includes but is not limited to a display, a television, a tablet computer, a mobile communication terminal, etc.

[0088] 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 is an example of the synthesis process of the compounds of the present invention.

[0089] Synthesis Example 1

[0090] Synthesis of Compound A1:

[0091]

[0092] 100 mmol of 2,9-dichloro-1,10-phenanthroline, 100 mmol of 4-biphenylboronic 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 carried out at 60 °C for 12 h. After the reaction was completed, the reaction was stopped, and the reactants were cooled to room temperature. Water was added, and the mixture was filtered and washed with water. The obtained solid was purified by recrystallization with toluene to obtain a white powder M1. Among them, the addition amount of Pd(PPh3)4 was 1 mol% of 2,9-dichloro-1,10-phenanthroline.

[0093] 100 mmol of M1, 100 mmol of 4-trimethylsilylbenzeneboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of tetrahydrofuran (THF) and 200 mL of water were added to a reaction flask, and 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) was added. The reaction was carried out at 60 °C for 12 h. After the reaction was completed, the reaction was stopped, and the reactants were cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain white powder A1. Among them, the addition amount of Pd(PPh3)4 was 1 mol% of M1.

[0094] 1 H NMR (400 MHz, Chloroform) δ 8.69 (d, J = 8.0 Hz, 2H), 8.35 (d, J = 8.0 Hz, 2H), 8.14 (d, J = 8.4 Hz, 2H), 7.85 (t, J = 7.6 Hz, 3H), 7.75 (d, J = 7.6 Hz, 2H), 7.60 (d, J = 8.4 Hz, 3H), 7.54 - 7.42 (m, 3H), 7.34 (d, J = 10.0 Hz, 2H), 0.25 (s, 9H).

[0095] Synthesis Example 2

[0096] Synthesis of Compound A2:

[0097]

[0098] 100 mmol of p-chlorobromobenzene, 100 mmol of 2-naphthaleneboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of tetrahydrofuran (THF) and 200 mL of water were added to a reaction flask, and 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) was added. The reaction was carried out at 60 °C for 12 h. After the reaction was completed, the reaction was stopped, and the reactants were cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain white powder M1. Among them, the addition amount of Pd(PPh3)4 was 1 mol% of p-chlorobromobenzene.

[0099] 100 mmol of M1, 100 mmol of bis(pinacolato)diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane were added to a reaction flask, and 1 mol% of Pd(PPh3)4 was added. The reaction was carried out at 100 °C for 12 h. After the reaction was completed, the reaction was stopped, and the reactants were cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain white powder M2. Among them, the addition amount of Pd(PPh3)4 was 1 mol% of M1.

[0100] Add 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 into a reaction flask, and add 1 mol% of Pd(PPh3)4. React at 60 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder M3. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of 2,9-dichloro-1,10-phenanthroline.

[0101] Add 100 mmol of 4-bromo-tetraphenylsilane, 100 mmol of bis(pinacolato)diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane into a reaction flask, and add 1 mol% of Pd(PPh3)4. React at 100 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder M4. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of 4-bromo-tetraphenylsilane.

[0102] Add 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 into a reaction flask, and add 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4). React at 60 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder A2. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of M3.

[0103] 1H NMR (400 MHz, Chloroform) δ 8.69 (d, J = 8.0 Hz, 2H), 8.36 (d, J = 8.0 Hz, 2H), 8.24 (d, J = 8.0 Hz, 2H), 8.12 - 7.97 (m, 3H), 7.86 (t, J = 8.4 Hz, 3H), 7.66 - 7.54 (m, 6H), 7.50 - 7.42 (m, 6H), 7.40 - 7.26 (m, 12H).

[0104] Synthesis Example 3

[0105] Synthesis of Compound A6:

[0106]

[0107] Add 100 mmol of 2-bromo-5-chloropyridine, 100 mmol of 4-(trimethylsilyl)phenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of tetrahydrofuran (THF) and 200 mL of water into a reaction flask, and add 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4). React at 60 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder M1. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of 2-bromo-5-chloropyridine.

[0108] Add 100 mmol of M1, 100 mmol of bis(pinacolato)diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane into a reaction flask, and add 1 mol% of Pd(PPh3)4. React at 100 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder M2. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of M1.

[0109] Add 100 mmol of 2,9-dichloro-1,10-phenanthroline, 100 mmol of 3-dibenzofuranboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF and 200 mL of water into a reaction flask, and add 1 mol% of Pd(PPh3)4. React at 60 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder M3. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of 2,9-dichloro-1,10-phenanthroline.

[0110] Add 100 mmol of M2, 100 mmol of M3, 41.4 g of potassium carbonate (300 mmol), 800 mL of tetrahydrofuran (THF) and 200 mL of water into a reaction flask, and add 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4). React at 60 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder A6. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of M2.

[0111] 1H NMR (400 MHz, Chloroform) δ 9.38 (s, 1H), 8.42 - 8.25 (m, 4H), 8.15 (d, J = 8.4 Hz, 2H), 7.99 (t, J = 8.0 Hz, 3H), 7.88 (d, J = 8.4 Hz, 1H), 7.78 (d, J = 8.0 Hz, 1H), 7.68 (d, J = 8.0 Hz, 1H), 7.62 - 7.54 (m, 4H), 7.43 - 7.28 (m, 3H), 0.25 (s, 9H).

[0112] Synthesis Example 4

[0113] Synthesis of Compound A13:

[0114]

[0115] Add 100 mmol of 2 - bromo - 5 - chloropyridine, 100 mmol of 4 - (trimethylsilyl)phenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of tetrahydrofuran (THF) and 200 mL of water into a reaction flask, and add 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4). React at 60 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder M1. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of 2 - bromo - 5 - chloropyridine.

[0116] Add 100 mmol of M1, 100 mmol of bis(pinacolato)diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane into a reaction flask, and add 1 mol% of Pd(PPh3)4. React at 100 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder M2. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of M1.

[0117] Add 100 mmol of diphenylmethylsilane, 100 mmol of 4 - chlorobromobenzene, 41.4 g of potassium carbonate (300 mmol), 800 mL of toluene into a reaction flask, and add 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4). React at 100 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder M3. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of diphenylmethylsilane.

[0118] Add 100 mmol of M3, 100 mmol of bis(pinacolato)diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane into a reaction flask, and add 1 mol% of Pd(PPh3)4. React at 100 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder M4. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of M3.

[0119] Add 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 into a reaction flask, and add 1 mol% of Pd(PPh3)4. React at 60 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder M5. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of 2,9-dichloro-1,10-phenanthroline.

[0120] Add 100 mmol of M2, 100 mmol of M5, 41.4 g of potassium carbonate (300 mmol), 800 mL of tetrahydrofuran (THF) and 200 mL of water into a reaction flask, and add 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4). React at 60 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder A13. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of M2.

[0121] 1H NMR (400 MHz, Chloroform) δ 9.37 (s, 1H), 8.39 (s, 1H), 8.39 - 8.24 (m, 5H), 8.15 (d, J = 7.2 Hz, 2H), 8.01 (d, J = 8.0 Hz, 1H), 7.74 - 7.55 (m, 6H), 7.50 - 7.42 (m, 4H), 7.40 - 7.28 (m, 7H), 0.66 (s, 3H), 0.25 (s, 9H).

[0122] Synthesis Example 5

[0123] Synthesis of Compound A17:

[0124]

[0125] Add 100 mmol of 2-bromo-5-chloropyridine, 100 mmol of 4-(trimethylsilyl)phenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of tetrahydrofuran (THF) and 200 mL of water into a reaction flask, and add 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4). React at 60 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder M1. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of 2-bromo-5-chloropyridine.

[0126] Add 100 mmol of M1, 100 mmol of bis(pinacolato)diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane into a reaction flask, and add 1 mol% of Pd(PPh3)4. React at 100 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder M2. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of M1.

[0127] Add 100 mmol of 2,9-dichloro-1,10-phenanthroline, 200 mmol of M2, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF and 200 mL of water into a reaction flask, and add 2 mol% of Pd(PPh3)4. React at 60 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder A17. Among them, the addition amount of Pd(PPh3)4 is 2 mol% of 2,9-dichloro-1,10-phenanthroline.

[0128] 1H NMR (400 MHz, Chloroform) δ 9.32 (s, 2H), 8.34 (t, J = 9.2 Hz, 4H), 8.15 (d, J = 8.4 Hz, 4H), 8.01 (d, J = 8.0 Hz, 4H), 7.68 (d, J = 8.4 Hz, 2H), 7.58 (d, J = 8.4 Hz, 4H), 0.25 (s, 18H).

[0129] Synthesis Example 6

[0130] Synthesis of Compound A20:

[0131]

[0132] Add 100 mmol of 5-chlorophenanthroline, 100 mmol of 4-chlorophenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of tetrahydrofuran (THF), and 200 mL of water into a reaction flask, and add 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4). React at 60 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactants to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder M1. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of 5-chlorophenanthroline.

[0133] Add 100 mmol of M1, 100 mmol of bis(pinacolato)diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane into a reaction flask, and add 1 mol% of Pd(PPh3)4. React at 100 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactants to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder M2. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of M1.

[0134] Add 100 mmol of 2,9-dichlorophenanthroline, 100 mmol of 4-(trimethylsilyl)phenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF, and 200 mL of water into a reaction flask, and add 1 mol% of Pd(PPh3)4. React at 60 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactants to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder M3. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of 2,9-dichlorophenanthroline.

[0135] Add 100 mmol of M2, 100 mmol of M3, 41.4 g of potassium carbonate (300 mmol), 800 mL of tetrahydrofuran (THF), and 200 mL of water into a reaction flask, and add 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4). React at 60 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactants to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder A20. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of M2.

[0136] 1H NMR (400 MHz, Chloroform) δ 8.80 (d, J = 8.0 Hz, 1H), 8.72 (d, J = 10.0 Hz, 3H), 8.39 (d, J = 10.0 Hz, 2H), 8.20 - 8.06 (m, 4H), 7.92 (s, 1H), 7.90 (d, J = 7.6 Hz, 1H), 7.59 (d, J = 8.0 Hz, 3H), 7.39 - 7.21 (m, 6H), 0.25 (s, 9H).

[0137] Synthesis Example 7

[0138] Synthesis of Compound A28:

[0139]

[0140] Add 100 mmol of p-chlorobromobenzene, 100 mmol of 4-(trimethylsilyl)phenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of tetrahydrofuran (THF) and 200 mL of water into a reaction flask, and add 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4). React at 60 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder M1. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of p-chlorobromobenzene.

[0141] Add 100 mmol of M1, 100 mmol of bis(pinacolato)diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane into a reaction flask, and add 1 mol% of Pd(PPh3)4. React at 100 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder M2. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of M1.

[0142] Add 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 into a reaction flask, and add 1 mol% of Pd(PPh3)4. React at 60 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder M3. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of 2,9-dichloro-1,10-phenanthroline.

[0143] Add 100 mmol of 2-chloro-4,6-diphenylpyrimidine, 100 mmol of 4-chlorophenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF and 200 mL of water into a reaction flask, and add 1 mol% of Pd(PPh3)4. React at 60 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder M4. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of 2-chloro-4,6-diphenylpyrimidine.

[0144] Add 100 mmol of M4, 100 mmol of bis(pinacolato)diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane into a reaction flask, and add 1 mol% of Pd(PPh3)4. React at 100 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder M5. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of M4.

[0145] Add 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 into a reaction flask, and add 1 mol% of Pd(PPh3)4. React at 60 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder A28. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of M3.

[0146] 1H NMR (400 MHz, Chloroform) δ 8.72 (s, 1H), 8.70 (d, J = 8.0 Hz, 2H), 8.45 - 8.30 (m, 4H), 8.23 (s, 1H), 7.96 - 7.82 (m, 7H), 7.76 - 7.75 (m, 3H), 7.61 - 7.45 (m, 9H), 7.34 (d, J = 10.0 Hz, 2H), 0.25 (s, 9H).

[0147] Synthesis Example 8

[0148] Synthesis of Compound A33:

[0149]

[0150] Add 100 mmol of 2-bromo-5-chloropyridine, 100 mmol of 4-(trimethylsilyl)phenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of tetrahydrofuran (THF), and 200 mL of water into a reaction flask, and add 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4). React at 60 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder M1. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of 2-bromo-5-chloropyridine.

[0151] Add 100 mmol of M1, 100 mmol of bis(pinacolato)diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane into a reaction flask, and add 1 mol% of Pd(PPh3)4. React at 100 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder M2. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of M1.

[0152] Add 100 mmol of M2, 100 mmol of 4-chlorophenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 mL of tetrahydrofuran (THF), and 200 mL of water into a reaction flask, and add 1 mol% of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4). React at 60 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder M3. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of M2.

[0153] Add 100 mmol of M3, 100 mmol of bis(pinacolato)diboron, 41.4 g of potassium carbonate (300 mmol), 800 mL of dioxane into a reaction flask, and add 1 mol% of Pd(PPh3)4. React at 100 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder M4. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of M3.

[0154] Add 100 mmol of 2-chloro-1,10-phenanthroline, 100 mmol of M4, 41.4 g of potassium carbonate (300 mmol), 800 mL of THF and 200 mL of water into a reaction flask, and add 1 mol% of Pd(PPh3)4. React at 60 °C for 12 h. After the reaction is completed, stop the reaction, cool the reactants to room temperature, add water, filter, wash with water, and recrystallize and purify the obtained solid with toluene to obtain white powder A33. Among them, the addition amount of Pd(PPh3)4 is 1 mol% of 2-chloro-1,10-phenanthroline.

[0155] 1H NMR (400 MHz, Chloroform) δ 8.86 (s, 1H), 8.76 (d, J = 8.0 Hz, 1H), 8.64 (d, J = 10.0 Hz, 2H), 8.42 (d, J = 8.8 Hz, 2H), 8.16 (d, J = 8.0 Hz, 2H), 8.02 (d, J = 8.0 Hz, 1H), 7.90 (t, J = 7.6 Hz, 2H), 7.61 - 7.54 (m, 4H), 7.30 (d, J = 9.2 Hz, 1H), 7.22 (d, J = 8.4 Hz, 2H), 0.25 (s, 9H).

[0156] Other compounds of the present invention can be synthesized by selecting appropriate raw materials according to the idea of the above synthesis example, or any other appropriate methods and raw materials can be selected for synthesis.

[0157] Example 1

[0158] Ultrasonically treat a glass substrate coated with an ITO transparent conductive layer with a thickness of 150 nm in a commercial cleaning agent, rinse it in deionized water, ultrasonically remove oil in an acetone-ethanol mixed solvent, bake it in a clean environment until all moisture is removed, clean it with ultraviolet light and ozone, and bombard the surface with a low-energy cation beam to obtain a glass substrate with an anode;

[0159] Then, place the above glass substrate with an anode in a vacuum chamber, evacuate to less than 10-5 Torr, and vacuum deposit a first hole injection layer 231 on the anode layer film of the above glass substrate with an anode. The material of the first hole injection layer 231 includes a hole injection layer material HT-11 and a p-type dopant p-1, and vapor deposition is carried out by the method of multi-source co-evaporation. Among them, adjust the vapor deposition rate of the hole injection layer material HT-11 to 0.1 nm / s, and the vapor deposition rate of the p-type dopant p-1 is 3% of the vapor deposition rate of the hole injection layer material HT-11. The total vapor deposition film thickness is 10 nm; the hole injection layer material HT-11 and the p-type dopant p-1 have the following structures:

[0160]

[0161] Then, the hole transport layer material HT-5 is vacuum-evaporated on the first hole injection layer as the first hole transport layer 241. Among them, the evaporation rate is 0.1 nm / s, and the evaporation film thickness is 80 nm. The structure of the hole transport layer material HT-5 is as follows:

[0162]

[0163] Then, the first light-emitting layer 251 is vacuum-evaporated on the first hole transport layer. The first light-emitting layer includes a light-emitting layer host material BH-2 and a light-emitting layer guest material BD-1, and the evaporation is carried out by the method of multi-source co-evaporation. Among them, the evaporation rate of the light-emitting layer host material BH-2 is adjusted to 0.1 nm / s, the evaporation rate of the light-emitting layer guest material BD-1 is 3% of the evaporation rate of the light-emitting layer host material BH-2, and the evaporation film thickness is 30 nm; the structures of the light-emitting layer host material BH-2 and the light-emitting layer guest material BD-1 are as follows:

[0164]

[0165] Then, the first electron transport layer 261 is vacuum-evaporated on the first light-emitting layer. The material of the first electron transport layer is compound ET30 and LiQ. Among them, the evaporation rate of compound ET30 is 0.1 nm / s, the evaporation rate ratio of compound ET30 and LiQ is 7:3, and the total evaporation film thickness is 30 nm; the structures of compound ET30 and LiQ are as follows:

[0166]

[0167] The above first hole injection layer, first hole transport layer, first light-emitting layer and first electron transport layer together form the first light-emitting unit;

[0168] On the first electron transport layer which is the uppermost layer in the first light-emitting unit, the compound A1 provided by the present invention and ytterbium (Yb) are evaporated to form the charge generation layer 27. Among them, the evaporation rate of compound A1 is 0.01 nm / s, the evaporation rate ratio of compound A1 and Yb is 99:1, and the total evaporation film thickness is 10 nm;

[0169] The second hole injection layer 232 is evaporated on the charge generation layer. The material of the second hole injection layer includes the hole injection layer material HT-11 and the p-type dopant p-1. Among them, the evaporation rate of the hole injection layer material HT-11 is adjusted to 0.1 nm / s, the evaporation rate ratio of the hole injection layer material HT-11 and the p-type dopant p-1 is 99:1, and the total evaporation film thickness is 10 nm;

[0170] Then, a hole transport layer material HT-5 is vacuum-evaporated on the second hole injection layer as the second hole transport layer 242, where the evaporation rate is 0.1 nm / s and the evaporation film thickness is 80 nm;

[0171] Then, a second light-emitting layer is vacuum-evaporated on the second hole transport layer. The second light-emitting layer 252 includes a light-emitting layer host material BH-2 and a light-emitting layer guest material BD-1, and is evaporated by a multi-source co-evaporation method. Among them, the evaporation rate of the light-emitting layer host material BH-2 is adjusted to 0.1 nm / s, and the evaporation rate of the light-emitting layer guest material BD-1 is 3% of the evaporation rate of the light-emitting layer host material BH-2, and the total evaporation film thickness is 30 nm;

[0172] Then, a second electron transport layer 262 is vacuum-evaporated on the second light-emitting layer. The electron transport material is a compound ET30 and LiQ. Among them, the evaporation rate of the compound ET30 is 0.1 nm / s, and the evaporation rate ratio of the compound ET30 and LiQ is 7:3, and the total evaporation film thickness is 30 nm;

[0173] The above second hole injection layer, second hole transport layer, second light-emitting layer and second electron transport layer together constitute the second light-emitting unit;

[0174] Then, LiF with a thickness of 0.5 nm is vacuum-evaporated on the uppermost second electron transport layer in the second light-emitting unit as the electron injection layer 28, where the evaporation rate is 0.1 nm / s;

[0175] Finally, an Al layer with a thickness of 150 nm is vacuum-evaporated on the electron injection layer 28 as the cathode electrode 29 of the organic electroluminescent device, where the evaporation rate is 0.1 nm / s.

[0176] Example 2-8

[0177] Except that the charge generation layer materials are replaced with A2, A6, A13, A17, A20, A28, A33 instead of A1 respectively, the rest are the same as in Example 1.

[0178] Example 9

[0179] Except that the first electron transport layer is removed and the thickness of the charge generation layer of the present invention is increased to 20 nm, and the ratio to the metal Yb remains unchanged at (99:1), the rest are the same as in Example 1.

[0180] Comparative Example 1

[0181] Except that the charge generation layer material is selected as CGL00R1 to replace A1, the rest are the same as in Example 1;

[0182]

[0183] Comparative Example 2

[0184] Except that the charge generation layer material is selected as CGL00R to replace A1, the rest is the same as in Example 1;

[0185]

[0186] The following performance measurements were carried out on the organic electroluminescent devices prepared by the above process:

[0187] At the same brightness, a digital source meter and a luminance meter were used to measure the driving voltage, current efficiency and device lifetime of the organic electroluminescent devices prepared in Examples 1 to 9 and Comparative Examples 1 to 2. 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: using a luminance meter at 1000 cd / m 2 brightness, keeping a constant current, and measuring the time when the brightness of the organic electroluminescent device dropped to 950 cd / m 2 The unit is hours. The results are shown in Table 1.

[0188] Table 1. Performance results of organic electroluminescent devices

[0189]

[0190]

[0191] As can be seen from Table 1, the organic electroluminescent devices prepared in Examples 1 to 8 use the compounds A1, A2, A6, A13, A17, A20, A28, and A33 provided by the present invention as the first charge generation layer material. Compared with Comparative Examples 1 and 2 in which known materials in the prior art are used as the charge generation layer material of the organic electroluminescent device, the organic electroluminescent device of the present invention has a lower driving voltage, a higher current efficiency, and a longer LT95 lifetime. It can be seen from Example 9 that when the first electron transport layer is removed and the first charge generation layer material is thickened to be used for electron transport, the same efficient electron transport effect can be maintained, and the device maintains a low voltage, high efficiency, and long life. Thus, it shows that when the compound of formula (I) is used as the charge generation material for the organic electroluminescent device, the driving voltage can be effectively reduced, the current efficiency can be improved, and the device lifetime can be extended. The materials of the present invention have a significant performance improvement especially in improving the efficiency of the organic electroluminescent device and extending the lifetime of the organic electroluminescent device, and an organic electroluminescent device with good performance can be obtained.

[0192] The above are only the preferred embodiments of the present invention and are not intended to limit the protection scope of the present invention. Any modifications, equivalent replacements, improvements, etc. made within the spirit and principle of the present invention are all included within the protection scope of the present invention.

Claims

1. A silicon-based substituted phenanthroline compound, characterized in that, Its structure is as shown in formula (I): Wherein, R 1 -R 6 Each independently selected from C1-C3 alkanes, unsubstituted or Rc-substituted C6-C30 aryl groups, unsubstituted or Rc-substituted C3-C30 heteroaryl groups; L 1 and L 2 are each independently selected from a chemical bond, an unsubstituted or Rc-substituted C6-C30 arylene group, and an unsubstituted or Rc-substituted C3-C30 heteroarylene group, and L 1 and L 2 are not simultaneously a chemical bond; m and n are each independently selected from 0 and 1, and m + n ≥ 1; The heteroatoms on the heteroaryl or heteroarylene are each independently selected from O, S or N; The substituents Rc of each group are each independently selected from hydrogen, deuterium, halogen, nitro, cyano, C1-C4 alkyl, phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl or naphthyl.

2. The compound according to claim 1, characterized in that, Said R 1 -R 6 each independently selected from C1-C3 alkanes, unsubstituted or Rc-substituted C6-C18 aryls, unsubstituted or Rc-substituted C3-C18 heteroaryls; and / or, The said L 1 , L 2 are each independently selected from a chemical bond, an unsubstituted or Rc-substituted C6-C18 arylene group, and an unsubstituted or Rc-substituted C3-C30 heteroarylene group.

3. The compound according to claim 1, characterized in that, Said R 1 -R 6 Each independently selected from methyl, ethyl, isopropyl, and the following groups of compounds which are unsubstituted or substituted by Rc: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, dibenzofuran, dibenzothiophene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, spirofluorene.

4. The compound according to claim 1, characterized in that, The L 1 , L 2 are each independently selected from a chemical bond and groups of the following compounds which are unsubstituted or substituted by Rc: phenyl, pyridyl, pyrimidyl, quinoxalinyl, quinazolinyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylenyl, fluorenyl, anthryl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl.

5. The compound according to claim 1, characterized in that, The compound of formula (I) is selected from the compounds shown in A1 to A35 below:

6. An organic electroluminescent device, characterized in that, Comprising a charge generation layer and an electron transport layer, and the charge generation layer material comprises the compound according to any one of claims 1 to 5.

7. The organic electroluminescent device according to claim 6, characterized in that, The charge generation layer material includes metal Li or Yb, and based on the mass of the charge generation layer material, the mass percentage content of the metal Li or Yb is 0.5% - 2.5%.

8. The organic electroluminescent device according to claim 6, characterized in that, The thickness of the charge generation layer is 10 nm - 30 nm, and the thickness of the electron transport layer is 10 nm - 40 nm.

9. A display device, characterized in that, It comprises the organic electroluminescent device according to any one of claims 6 - 8.

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