Organic electroluminescent material and organic electroluminescent device comprising same

Abstract

The invention belongs to the field of organic photoelectric materials, and discloses an organic electroluminescent material and an organic electroluminescent device containing the same. The structure of the organic electroluminescent material is as shown in a formula I: # imgabs0 #. When the organic electroluminescent material provided by the invention is used as a material in a luminescent layer, the driving voltage of a device can be reduced, the maximum external quantum efficiency of the device can be improved, and the phosphorescence lifetime of the device can be prolonged.

Description

Technical Field

[0001] The present invention belongs to the field of organic optoelectronic materials, and particularly relates to an organic electroluminescent material and an organic electroluminescent device comprising the same. Background Art

[0002] An organic electroluminescent device (OLED) is a device that converts electrical energy into light by applying electricity to an organic electroluminescent material, and generally has a structure including an anode, a cathode, and an organic layer between the anode and the cathode. The organic layer of the organic EL device may be composed of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (which includes a host material and a doping material), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc., and the materials used for the organic layer are classified into hole injection materials, hole transport materials, electron blocking materials, light-emitting materials, electron buffer materials, hole blocking materials, electron transport materials, electron injection materials, etc. In the organic EL device, due to the applied voltage, holes are injected from the anode into the light-emitting layer, electrons are injected from the cathode into the light-emitting layer, and high-energy excitons are formed by the recombination of holes and electrons. Through this energy, the organic light-emitting compound reaches an excited state, and light is emitted by the energy generated when the excited state of the organic light-emitting compound returns to the ground state.

[0003] However, the existing organic electroluminescent materials have low stability, poor matching degree between HOMO and LUMO energy levels and adjacent energy levels, resulting in the problem of unbalanced carrier mobility, and further causing problems such as a high driving voltage, low luminous efficiency, and short lifespan of the organic electroluminescent device comprising the organic electroluminescent material, seriously limiting the application of the organic electroluminescent device. Therefore, how to develop a high-performance light-emitting material that enables an organic electroluminescent device to have comprehensive characteristics such as high efficiency, long lifespan, and low voltage is a technical problem that needs to be solved urgently by those skilled in the art. Summary of the Invention

[0004] In view of the deficiencies of the prior art, the present invention discloses and provides an organic electroluminescent material and an organic electroluminescent device comprising the same. Using the organic electroluminescent material provided by the present invention as the material in the light-emitting layer can not only reduce the driving voltage of the device, but also improve the maximum external quantum efficiency of the device and extend the phosphorescence lifespan of the device.

[0005] To achieve the above object, the following technical solutions are adopted:

[0006] The first object of the present invention is to provide an organic electroluminescent material having the structure shown in General Formula I: ;

[0007] Wherein,

[0008] Selected from substituted or unsubstituted C3-C10 azacycles, and the connection position is N on the azacycle;

[0009] X is independently selected from O, S, Se, NRx, CRxRy, SiRxRy, GeRxRy; wherein, Rx and Ry are selected from hydrogen, methyl, -F, -D, -CN, -CD3, phenyl;

[0010] One of R1, R2, R3 and R4 is connected to and the rest are independently selected from hydrogen, deuterium, halogen, -CN, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, trimethylgermane, trimethylsilane and combinations thereof;

[0011] R5, R6, R7, R8 and R9 are each independently selected from hydrogen, -D, -CN, -F, C1-C20 alkyl partially or fully substituted with deuterium, cyclopentyl, cyclohexyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted C3-C20 cycloalkyl, any one or more combinations thereof;

[0012] R 10 、R 11 、R 12 、R 13 and R 14 are each independently selected from hydrogen, deuterium, halogen, -CN, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, trimethylgermane, trimethylsilane and combinations thereof, and two adjacent groups can form a cyclic structure;

[0013] R 15 、R 16 、R 17 、R 18 、R 19 、R 20 、R 21 and R 22 are each independently selected from hydrogen, -D, -CN, -F, -CF3, C1-C20 alkyl partially or fully substituted with deuterium, cyclopentyl, cyclohexyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 cycloalkyl, trimethylgermane, trimethylsilane, any one or more combinations thereof;

[0014] The hydrogen atoms in the above groups can be partially or fully deuterated.

[0015] Furthermore,

[0016] X is independently selected from O, S, Se, NRx, CRxRy, SiRxRy, GeRxRy; wherein, Rx and Ry are selected from hydrogen, methyl;

[0017] selected from substituted or unsubstituted piperidinyl, substituted or unsubstituted pyrrolidinyl;

[0018] At least one of R1, R2, R3 and R4 is not hydrogen, and each is independently selected from hydrogen, -F, -CD3, -CN, phenyl, methyl, ethyl, propyl, butyl, pentyl;

[0019] R5, R6, R7, R8 and R9 are each independently selected from hydrogen, -D, -F, -CN, -CD3, substituted or unsubstituted phenyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted cyclohexyl, and two adjacent groups can form a cyclic structure;

[0020] R 10 、R 11 、R 12 、R 13 and R 14 are each independently selected from hydrogen, -D, -F, -CN, -CD3, substituted or unsubstituted phenyl, methyl, ethyl, propyl, butyl, trimethylgermyl, trimethylsilyl, and two adjacent groups can form a cyclic structure or any one or a combination of at least two of the following groups;

[0021] ;

[0022] The above alkyl groups and aryl groups can be partially deuterated or fully deuterated.

[0023] It should be noted that the above substituted or unsubstituted is substituted by one, two or more of the following substituents: deuterium; halogen group; cyano group; C1-C20 alkyl group; C3-C20 cycloalkyl group; C6-C30 aryl group; C3-C20 heterocyclic group, or substituted by substituents in which two or more of the above-mentioned substituents are connected, or has no substituents; and the above * is the connection position.

[0024] Even further, selected from the following groups:

[0025] .

[0026] Furthermore, the ligand is selected from the following structures:

[0027] 。

[0028] Furthermore, the ligand is selected from the following structures:

[0029] 。

[0030] In the present invention, the organic electroluminescent material is selected from any one of the following structures:

[0031] 。

[0034] Only some specific structural forms are listed above. However, this series of organic electroluminescent materials are not limited to the above molecular structures. Any simple transformation of some simple groups, their substituted groups, and substitution positions can yield other specific molecular structures, which will not be elaborated one by one here.

[0035] In the present invention, the preparation process of the organic electroluminescent material of formula I is as follows:

[0036] ;

[0037] wherein, R1 - R 22 , A and X are as defined above and will not be elaborated further.

[0038] The preparation operations are as follows:

[0039] Under nitrogen protection, the ligand of formula V', IrC13·3H2O are placed into the reaction system, a mixed solution of ethylene glycol monoethyl ether and pure water is added, and the mixture is refluxed at 120 °C for 36 hours under nitrogen protection to obtain the intermediate of formula IV;

[0040] Silver trifluoromethanesulfonate is added to the intermediate of formula IV, and then dichloromethane and methanol are added to the system. The mixture is refluxed at 25 °C for 48 hours under nitrogen protection to obtain the intermediate of formula III;

[0041] The ligand of formula II is added to the intermediate of formula III, and then absolute ethanol is added to the system. The mixture is refluxed at 80 °C for 36 hours under nitrogen protection to obtain the organic electroluminescent material shown in formula I.

[0042] The second technical object of the present invention is to provide an organic electroluminescent device, which includes an anode, a cathode, and an organic material layer disposed between the anode and the cathode, and the organic material layer includes the organic electroluminescent material as described above.

[0043] Preferably, the organic material layer includes a light-emitting layer, the light-emitting layer includes a host material and a doping material, and the doping material includes the organic electroluminescent material as described above.

[0044] Preferably, the organic material layer further includes at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, and an electron injection layer.

[0045] Specifically, the organic electroluminescent device includes an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode, which are sequentially arranged.

[0046] Generally, an organic electroluminescent device includes a first electrode (anode) and a second electrode (cathode), and an organic material layer located between the electrodes. The organic material layer can be further divided into multiple regions. For example, the organic material layer can include a hole transport region, a light-emitting layer, and an electron transport region.

[0047] In a specific embodiment, a substrate can be used under the first electrode or above the second electrode. The substrate is made of glass or polymer materials with excellent mechanical strength, thermal stability, waterproofness, and transparency. In addition, a thin film transistor (TFT) can also be provided on the substrate for display purposes.

[0048] The first electrode can be formed by sputtering or depositing a material used as the first electrode on the substrate. When the first electrode is used as the anode, oxide transparent conductive materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), and any combination thereof can be used. In addition, the anode material can also be selected from materials and their combinations that are helpful for hole injection other than the listed anode materials, including known materials suitable for making anodes. When the first electrode is used as the cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof can be used. In addition to the listed cathode materials, the cathode material can also be materials and their combinations that are helpful for electron injection, including known materials suitable for making cathodes.

[0049] The organic material layer can be formed on the electrode by methods such as vacuum thermal evaporation, spin coating, printing, etc. The compounds used as the organic material layer can be organic small molecules, organic macromolecules, polymers, and their combinations. The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multi-layer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[0050] The materials for the hole transport layer can be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers, or polymers containing conductive dopants such as poly(phenylene vinylene), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), aromatic amine derivatives such as the compounds shown in HT-1 to HT-30 below, or any combination thereof: 。

[0051] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds. For example, the hole injection layer can be one or more of the compounds in HT-1 to HT-30 above, or one or more of the compounds in HI-1 to HI-3 below; it can also be one or more of the compounds in HT-1 to HT-30 above doped with one or more of the compounds in HI-1 to HI-3 below:

[0052] 。

[0053] The OLED organic material layer may further include an electron transport region between the light-emitting layer and the cathode. The electron transport region can be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region can also be a multi-layer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0054] The materials for the electron transport layer can be selected from, but not limited to, one or more combinations of the following listed ET-1 to ET-36:

[0055] 。

[0056] The device also includes an electron injection layer between the electron transport layer and the cathode. The materials for the electron injection layer include, but are not limited to, one or more combinations of the following listed:

[0057] LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca.

[0058] According to the above technical solutions, compared with the prior art, the present invention has the following beneficial effects:

[0059] The present invention provides an organic electroluminescent material. By selecting coordination with a specific heterocyclic ligand, changing the combination of substituents on 8-(pyridin-2-yl)benzofuro[2,3-b]pyridine, and adding -CN, -F, branched alkyl, substituted or unsubstituted piperidinyl, substituted or unsubstituted pyrrolidinyl, substituted or unsubstituted aryl, and substituted or unsubstituted cycloalkyl, an organic electroluminescent material is generated. The intermolecular spatial configuration is improved, and it has good spatial torsion ability, thereby avoiding the change of the position or activity of the substituent due to carrier migration. After the obtained organic electroluminescent material is used in an organic electroluminescent device, the maximum external quantum efficiency of the device is improved, the lifetime is prolonged, and the driving voltage is reduced. Description of the Drawings

[0060] In order to more clearly illustrate the technical solutions in the embodiments of the present invention or the prior art, the following will briefly introduce the drawings required for the description of the embodiments or the prior art. Obviously, the drawings in the following description are only the embodiments of the present invention. For those of ordinary skill in the art, without creative efforts, other drawings can also be obtained according to the provided drawings.

[0061] Figure 1 It is the nuclear magnetic resonance hydrogen spectrum of Z-1. Detailed Embodiments

[0062] The following will clearly and completely describe the technical solutions of the present invention in conjunction with the embodiments of the present invention and the relevant drawings. Obviously, the described embodiments are only a part of the embodiments of the present invention, rather than all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those of ordinary skill in the art without creative efforts belong to the scope of protection of the present invention.

[0063] The embodiments of the present invention specifically disclose an organic electroluminescent material and an organic electroluminescent device including the same.

[0064] The features and performance of the present invention will be further described in detail below in conjunction with specific embodiments.

[0065] Example 1

[0066]

[0067] Under nitrogen protection, 8-chloro-[1]benzofuro[2,3-b]pyridine (1 eq, CAS: 2747969-64-6) and anhydrous potassium carbonate (3 eq) were placed in the reaction system. Toluene, absolute ethanol, and purified water were added. Under nitrogen protection, Pd(PPh3)4 (0.015 eq) was added. (4-Chloropyridin-2-yl)boronic acid (1 eq, CAS: 870459-91-9) was added in three batches every 1 hour. After the addition was complete, the mixture was refluxed at 100 °C for 24 h under nitrogen protection, and then cooled to 25 °C. After the reaction was cooled, it was extracted with ethyl acetate, washed three times with saturated brine, dried over anhydrous magnesium sulfate, concentrated under reduced pressure. The crude product was subjected to column chromatography (200-300 mesh, 500 g) to remove impurities. The eluent was EA:PE = 1:15. The receiving solution was rotated until no liquid flowed out and dried in vacuo to obtain the intermediate 1 of the shown compound with a yield of 59.7%.

[0068]

[0069] Under nitrogen protection, intermediate 1 (1 eq) and anhydrous potassium carbonate (3 eq) were placed in the reaction system. Toluene, absolute ethanol, and purified water were added. Under nitrogen protection, Pd(PPh3)4 (0.015 eq) was added. [4-(4,4-Dimethylpiperidin-1-yl)phenyl]boronic acid (1 eq, CAS: 2766475-50-5) was added in three batches every 1 hour. After the addition was complete, the mixture was refluxed at 110 °C for 24 h under nitrogen protection, and then cooled to 25 °C. After the reaction was cooled, it was extracted with ethyl acetate, washed three times with saturated brine, dried over anhydrous magnesium sulfate, concentrated under reduced pressure. The crude product was subjected to column chromatography (200-300 mesh, 500 g) to remove impurities. The eluent was EA:PE = 1:20. The receiving solution was rotated until no liquid flowed out and dried in vacuo to obtain the compound of formula II-1 of the shown compound with a yield of 91.6%.

[0070]

[0071] Under a nitrogen protection system, the compound of formula V-1 (1 eq) and IrC13·3H2O (0.4 eq) were weighed and placed in the reaction system. A mixed solution of ethylene glycol monoethyl ether and purified water was added. The mixture was refluxed at 120 °C for 36 hours under nitrogen protection, and then cooled to room temperature. A precipitate was formed and filtered by suction. It was washed successively with water, absolute ethanol, and petroleum ether and dried to obtain the compound of formula IV-1 of the shown compound with a yield of 81.9%.

[0072]

[0073] Under a nitrogen protection system, weigh the compound of formula Ⅳ-1 (1 eq), add silver trifluoromethanesulfonate (2.2 eq), then add dichloromethane to the system, add methanol, reflux at 25 °C for 48 hours under nitrogen protection, cool to room temperature, concentrate the filtrate of column chromatography until a solid precipitates to obtain the compound of formula Ⅲ-1 with a yield of 94.6%.

[0074]

[0075] Under a nitrogen protection system, weigh the compound of formula Ⅲ-1 (1 eq), add the compound of formula Ⅱ-1 (2.2 eq), then add anhydrous ethanol to the system, reflux at 80 °C for 36 hours under nitrogen protection, filter by suction, wash with alcohol, and dry; use dichloromethane as the solvent, perform silica gel column chromatography, concentrate the filtrate until a solid precipitates to obtain the final compound Z-1 (11.78 g, yield 59.2%).

[0076] HPLC purity: greater than 99.5%;

[0077] MS (ESI, m / Z): [M + H]+: 933.38.

[0078] The 1H NMR spectrum of the compound Z-1 prepared in Example 1 is as Figure 1 shown.

[0079] In addition, it should be noted that other compounds of the present invention can be obtained by referring to the preparation methods of the above-listed examples, and will not be elaborated here one by one.

[0080] Device Example 1:

[0081] An organic electroluminescent device is prepared using the organic electroluminescent material of formula Z-1

[0082] Place an ITO glass substrate with a coating thickness of 1500 Å in distilled water and wash it twice, ultrasonically wash it for 30 minutes. After the distilled water washing is completed, ultrasonically wash it in sequence with solvents such as isopropanol, acetone, and methanol and then dry it. Transfer it to a plasma cleaner, wash the above substrate for 10 minutes, and send it to an evaporation coater.

[0083] First, deposit a hole injection layer of HI-1 with a thickness of 100 Å on ITO (anode), then deposit a hole transport layer of HT-4 with a thickness of 900 Å on the hole injection layer. Immediately deposit a light-emitting layer with a thickness of 400 Å of the host material 4,4'-N,N'-dicarbazole biphenyl ("CBP") and the doping material compound of formula Z-1 in a weight ratio of 90:10. Then deposit an electron transport layer of ET-4 with a thickness of 400 Å on the light-emitting layer. Immediately deposit an electron injection layer material Liq with a thickness of 150 Å on the electron transport layer. Finally, deposit a cathode material Al with a thickness of 1000 Å on the electron injection layer to obtain an organic electroluminescent device.

[0084] The structure of Liq is as follows:

[0085] 。

[0086] For the performance and luminescence characteristics test of the obtained device, a KEITHLEY 2400 source measure unit and a CS-2000 spectro-radiance meter were used for measurement to evaluate the driving voltage, lifespan, and luminous efficiency.

[0087] Device of Comparative Example 1 - Device of Comparative Example 4:

[0088] The difference from Device Example 1 is only that: the doping material compound formula Z-1 was respectively replaced with the structures shown in Comparative Example 1 - Comparative Example 4, and then an organic electroluminescent device (Device of Comparative Example 1 - Device of Comparative Example 4) was prepared according to the same method as in Device Example 1. The structures of the doping materials in the light-emitting layer are as follows:

[0089]

[0090] 。

[0091] Device Example 2 - Device Example 45:

[0092] Referring to the method of Device Example 1 above, the only difference is that the doping material compound formula Z-1 was respectively replaced with Z-8, Z-18, Z-22, Z-57, Z-78, Z-100, Z-144, Z-166, Z-173, Z-206, Z-255, Z-270, Z-311, Z-341, Z-356, Z-413, Z-430, Z-464, Z-480, Z-503, Z-540, Z-566, Z-579, Z-592, Z-603, Z-606, Z-622, Z-633, Z-667, Z-680, Z-693, Z-716, Z-744, Z-758, Z-786, Z-792, Z-804, Z-846, Z-866, Z-889, Z-910, Z-919, Z-1024, Z-1085, and then an organic electroluminescent device (Device Example 2 - Device Example 45) was prepared according to the same method as in Device Example 1.

[0093] The driving voltage, luminous efficiency, and lifespan of the organic electroluminescent devices obtained from the above Device Examples and Devices of Comparative Examples were characterized at a brightness of 15000 (nits), and the test results are shown in Table 1.

[0094] It should be noted that the relative value is the comparison result between numbers, usually expressed in the form of percentage or decimal, used to represent the degree of change of a number relative to other numbers. In addition, in the industrial field, the relative value can also be used to measure the degree of change in production efficiency, and evaluate the quality and stability of products, etc.

[0095] Table 1

[0096] It can be seen from Table 1 that:

[0097] 1. Through the comparison of device test data, it can be seen that by changing the combination of substituents on 8-(pyridin-2-yl)benzofuro[2,3-b]pyridine, organic electroluminescent materials are generated by adding -CN, -F, branched alkyl groups, substituted or unsubstituted piperidyl groups, substituted or unsubstituted pyrrolidinyl groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted cycloalkyl groups. By increasing the electron-withdrawing groups, the intermolecular spatial configuration is improved, and it has good spatial torsion ability, effectively regulating the HOMO and LUMO energy levels, thereby avoiding carrier migration. After using it as a specific doping material for the light-emitting layer and applying it to the organic electroluminescent device, the driving voltage of the device is reduced, thereby avoiding carrier migration. When the compound of the present application is used as a light-emitting layer doping material, the organic electroluminescent device prepared is compared with the organic electroluminescent device prepared in the comparative example, and the driving voltage is significantly reduced, and the luminous efficiency and lifetime are significantly improved.

[0098] 2. When the organic electroluminescent device prepared using the compound provided in the present application as the light-emitting layer doping material is compared with the organic electroluminescent devices prepared using the comparative examples 1-4 as the light-emitting layer doping materials, the driving voltage is significantly reduced, and the luminous efficiency is significantly enhanced.

[0099] The above description of the disclosed embodiments enables those skilled in the art to implement or use the present invention. Various modifications to these embodiments will be obvious to those skilled in the art, and the general principles defined herein can be implemented in other embodiments without departing from the spirit or scope of the present invention. Therefore, the present invention will not be limited to these embodiments shown herein, but will be accorded the widest scope consistent with the principles and novel features disclosed herein.

Claims

1. An organic electroluminescent material, characterized in that, The structure of the organic electroluminescent material is shown in Formula I: ； Among them, selected from substituted or unsubstituted C3-C10 azacycles, and the connection position is N on the azacycle; X is independently selected from O, S, Se, NRx, CRxRy, SiRxRy, GeRxRy; wherein, Rx and Ry are selected from hydrogen, methyl, -F, -D, -CN, -CD3, phenyl; One of R1, R2, R3 and R4 is connected to and the rest are independently selected from hydrogen, deuterium, halogen, -CN, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, trimethylgermyl, trimethylsilyl and combinations thereof; R5, R6, R7, R8 and R9 are each independently selected from hydrogen, -D, -CN, -F, C1-C20 alkyl which is fully or partially substituted by deuterium, cyclopentyl, cyclohexyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted C3-C20 cycloalkyl, any one or more combinations thereof; R 10 、R 11 、R 12 、R 13 and R 14 each independently selected from hydrogen, deuterium, halogen, -CN, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, trimethylgermyl, trimethylsilyl, and combinations thereof, and two adjacent groups may form a cyclic structure; R 15 、R 16 、R 17 、R 18 、R 19 、R 20 、R 21 and R 22 each independently selected from any one or more combinations of hydrogen, -D, -CN, -F, -CF3, C1-C20 alkyl which is fully or partially deuterium-substituted, cyclopentyl, cyclohexyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 cycloalkyl, trimethylgermane, trimethylsilane; The hydrogen atoms in the above groups are partially deuterated or fully deuterated.

2. The organic electroluminescent material according to claim 1, characterized in that, X is independently selected from O, S, Se, NRx, CRxRy, SiRxRy, GeRxRy; wherein, Rx and Ry are selected from hydrogen, methyl; selected from substituted or unsubstituted piperidinyl, substituted or unsubstituted pyrrolidinyl; At least one of R1, R2, R3 and R4 is not hydrogen, and they are each independently selected from hydrogen, -F, -CD3, -CN, phenyl, methyl, ethyl, propyl, butyl, pentyl; R5, R6, R7, R8 and R9 are each independently selected from hydrogen, -D, -F, -CN, -CD3, substituted or unsubstituted phenyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted cyclohexyl, and two adjacent groups can form a cyclic structure; R 10 、R 11 、R 12 、R 13 and R 14 are each independently selected from hydrogen, -D, -F, -CN, -CD3, substituted or unsubstituted phenyl, methyl, ethyl, propyl, butyl, trimethylgermyl, trimethylsilyl, and two adjacent groups may form a cyclic structure or any one or a combination of at least two of the following groups; ； The above alkyl and aryl are both partially deuterated or fully deuterated.

3. The organic electroluminescent material according to claim 1 or 2, wherein Substituted or unsubstituted with one, two or more substituents selected from the following: deuterium; halogen group; cyano group; C1-C20 alkyl; C3-C20 cycloalkyl; C6-C30 aryl; C3-C20 heterocyclic group, or substituted with substituents connected by two or more of the above-mentioned substituents, or without substituents; and * is the connection position.

4. The organic electroluminescent material according to claim 3, characterized in that, Selected from the following groups: 。 5. The organic electroluminescent material according to claim 1, characterized in that, Ligand Selected from the following structures: 。 6. The organic electroluminescent material according to claim 1, wherein Ligand Selected from the following structures: 。 7. The organic electroluminescent material according to claim 1, wherein The organic electroluminescent material is selected from one of the following structures, but not limited to this: .

8. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes an anode, a cathode, and an organic material layer disposed between the anode and the cathode; the organic material layer contains the organic electroluminescent material as described in claim 1.

9. The organic electroluminescent device according to claim 8, characterized in that, The organic electroluminescent device includes a light-emitting layer, and the light-emitting layer includes the organic electroluminescent material as described above.

10. The organic electroluminescent device according to claim 9, characterized in that, The light-emitting layer of the organic electroluminescent device includes a host material and a doping material; the doping material includes the organic electroluminescent material as described above.

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