Compound containing triazinyl and organic electroluminescent device

Abstract

According to the novel organic electroluminescent material provided by the invention, part of the benzofuro-carbazole group directly connected with the triazine group is deuterated, so that the chemical stability, photoelectric stability and thermal stability of the material structure are greatly improved, the stability of a device is improved, and the service life is further prolonged. According to the present invention, the P-type compound can form the good Premix material, the P-type compound has good P / N stability and mass production stability during the evaporation process, and the formed Premix material has more balanced carrier mobility, such that the efficiency of the device is substantially improved, and the service life of the device is substantially prolonged.

Description

Technical Field

[0001] The present invention relates to the technical field of organic electroluminescence, and in particular to a compound containing a triazine group and an organic electroluminescent device. Background Art

[0002] Organic electroluminescence usually refers to an organic light-emitting diode (OLED) that uses electric current to drive an organic semiconductor film to emit light, thereby achieving the purpose of display.

[0003] An organic electroluminescent device consists of a cathode, an anode, and an organic layer disposed between them. The organic layer structure of OLED devices currently used in industry is typically multilayered, including, for example, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer. For an OLED device containing these layers, when a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the holes and electrons meet, excitons are formed. When the excitons transfer energy to the dopant material, light is emitted through radiative transitions in the dopant material.

[0004] In existing OLED devices, the poor compatibility of green light hosts prevents efficient energy transfer to the dopant material, reducing the efficiency of conductive OLED devices. Furthermore, the lack of deuteration at active sites and sites with high electron density within the material molecules results in poor chemical, thermal, and photoelectric stability, which in turn impacts device lifespan. Furthermore, the P / N ratio of current green light hosts fluctuates significantly with increasing vapor deposition time, leading to significant fluctuations in device performance, poor stability, and low yields.

[0005] The premix material formed by combining the N-type and P-type compounds of the present invention exhibits excellent thermal, chemical, and photoelectric stability due to deuteration at the active sites of their respective structures. Furthermore, the premix material formed by the compounds of the present invention exhibits balanced carrier mobility, further broadening the exciton recombination zone, thereby improving device lifespan and efficiency. Summary of the Invention

[0006] The purpose of the present invention is to provide a compound containing a triazine group and an organic electroluminescent device based on the existing technology.

[0007] To achieve the above object, the present invention provides a compound, the structural formula of which is shown in Formula 1 below:

[0008]

[0009] X is O, S or Se;

[0010] Ar1 and Ar2 are each independently selected from the following groups: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, spirobifluorenyl, 9,9-dimethylfluorenyl, each of which may be further substituted by one or more of deuterium, fluorine, cyano, C1-C10 alkyl, C1-C10 deuterated alkyl, C1-C10 cycloalkyl, C1-C10 deuterated cycloalkyl, C6-C30 aryl, C6-C30 deuterated aryl, C5-C30 heteroaryl, and C5-C30 deuterated heteroaryl;

[0011] L1-L3 are each independently selected from a single bond, phenyl, biphenyl, and naphthyl, each of which may be further substituted with one or more of deuterium, fluorine, cyano, C1-C10 alkyl, C6-C18 aryl, and C5-C20 heteroaryl;

[0012] A1-A6 are each independently selected from one or more of deuterium, fluorine, cyano, phenyl, biphenyl, naphthyl, and pyridyl, wherein A1-A6 contain at least one deuterium.

[0013] Preferably, its structural formula is shown in Formula 2 below:

[0014]

[0015] X is O, S or Se;

[0016] Ar1 and Ar2 are each independently selected from the following groups: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, pyridyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, spirobifluorenyl, 9,9-dimethylfluorenyl, each of which may be further substituted with deuterium, fluorine, cyano, deuterated or undeuterated phenyl, biphenyl, methyl, ethyl, tert-butyl, cyclopentyl, cyclohexyl or one or more thereof;

[0017] L1-L3 are each independently selected from a single bond, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, and pyridyl.

[0018] Preferably,

[0019] X is O or S;

[0020] Ar1 and Ar2 are each independently selected from the following groups: phenyl, biphenyl, terphenyl, pyridyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, spirobifluorenyl, 9,9-dimethylfluorenyl, each of which may be further substituted by deuterium, fluorine, cyano, deuterated or undeuterated groups: phenyl, biphenyl, methyl, ethyl, tert-butyl, cyclopentyl, cyclohexyl or one or more thereof;

[0021] L1-L3 are each independently selected from a single bond, phenyl, deuterated phenyl, biphenyl, and deuterated biphenyl.

[0022] Preferably, its structural formula is shown in Formula 3 below:

[0023]

[0024] X is O or S;

[0025] Ar1 and Ar2 are each independently selected from the following groups: phenyl, biphenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, each of which may be further substituted with one or more of the following groups: phenyl, biphenyl, methyl, tert-butyl, deuterated or undeuterated;

[0026] L1 and L2 are each independently selected from a single bond, a phenyl group, a deuterated phenyl group, a biphenyl group, and a deuterated biphenyl group.

[0027] More preferably,

[0028] X is O or S;

[0029] Ar1 and Ar2 are each independently selected from the following groups: phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, each of which may be further substituted with one or more of deuterium, phenyl, deuterated phenyl, methyl, and tert-butyl;

[0030] L1 and L2 are each independently selected from a single bond, a phenyl group, a deuterated phenyl group, a biphenyl group, and a deuterated biphenyl group.

[0031] In a preferred embodiment, the compound of the present invention is any one of the following compounds:

[0032]

[0033]

[0034]

[0035]

[0036]

[0037] An organic electroluminescent device comprises a first electrode, a second electrode and an organic layer formed between the first electrode and the second electrode; wherein the organic layer contains the compound of the present invention.

[0038] Furthermore, the organic layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer; wherein the light-emitting layer contains the compound of the present invention.

[0039] Furthermore, the light-emitting layer further contains at least one of the following formula 5 or formula 6:

[0040]

[0041] in,

[0042] Ar4 and Ar5 are each independently selected from the following substituted or unsubstituted groups: C6-C30 aryl, C5-C30 heteroaryl, and the substituents of Ar4 and Ar5 are selected from one or more of deuterium, fluorine, cyano, C1-C10 alkyl, C1-C10 deuterated alkyl, C1-C10 cycloalkyl, C1-C10 deuterated cycloalkyl, C6-C30 aryl, C6-C30 deuterated aryl, and C5-C30 heteroaryl;

[0043] L4 and L5 are each independently selected from a single bond, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group, and the substituents of L4 and L5 are selected from one or more of deuterium, fluorine, cyano, C1-C10 alkyl, C6-C18 aryl, and C5-C20 heteroaryl groups;

[0044] R2-R5 are each independently selected from hydrogen, deuterium, fluorine, cyano, deuterated or undeuterated groups: one or more of phenyl, biphenyl, methyl, ethyl, and tert-butyl;

[0045] m and p are each independently an integer from 0 to 7;

[0046] k is an integer from 0 to 6;

[0047] g is an integer from 0 to 4.

[0048] Furthermore, the light-emitting layer contains a light-emitting host material, which is a mixture of the compound of the present invention and any one or more of compounds P-1 to P-88. Compounds P-1 to P-88 are as follows:

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055] An electronic display device containing the organic electroluminescent device of the present invention.

[0056] An OLED lighting device comprising the organic electroluminescent device of the present invention.

[0057] The room temperature described in the present invention is 25±5°C.

[0058] As a further improvement of the present invention,

[0059] Compared with the prior art, the present invention has the following beneficial effects:

[0060] The present invention designs a new type of organic electroluminescent material with the following excellent properties:

[0061] 1. Partial deuteration of the benzofuranocarbazole group directly connected to the triazine group greatly improves the chemical stability, photoelectric stability and thermal stability of the material structure, improves the stability of the device, and thus increases the lifespan.

[0062] 2. It can form a good Premix material with the P-type compound of the present invention, has good P / N stability and mass production stability during the evaporation process, and the formed Premix material has a more balanced carrier mobility, thereby greatly improving the efficiency and life of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0063] Figure 1 A schematic structural diagram of an organic electroluminescent device provided by the present invention;

[0064] The numbers in the figure represent: 1-anode, 2-hole injection layer, 3-hole transport layer, 4-electron blocking layer, 5-light-emitting layer, 6-hole blocking layer, 7-electron transport layer, 8-electron injection layer, 9-cathode;

[0065] Figure 2 HPLC chart of compound 6 prepared in Example 1 of the present invention;

[0066] Figure 3 is the DSC spectrum of compound 6 prepared in Example 1 of the present invention, Figure 3 It can be seen that the melting point temperature Tm value of compound 6 is 298.33℃;

[0067] Figure 4 is the TGA spectrum of compound 6 prepared in Example 1 of the present invention, Figure 4 It can be seen that the thermal weight loss temperature Td value is 484.17℃; DETAILED DESCRIPTION

[0068] The present invention is described in detail below with reference to the various embodiments shown in the accompanying drawings, but it should be noted that these embodiments are not limitations of the present invention, and any equivalent transformations or substitutions in functions, methods, or structures made by ordinary technicians in this field based on these embodiments are all within the scope of protection of the present invention.

[0069] As used herein, the term "substituted" refers to the realignment of at least one hydrogen in the group with a deuterium, a hydrocarbyl, a hydrocarbon derivative, a halogen, or a cyano group (-CN). The term "unsubstituted" refers to the realignment of at least one hydrogen in the group with a deuterium, a hydrocarbyl, a hydrocarbon derivative, a halogen, or a cyano group (-CN). Examples of hydrocarbyl or hydrocarbon derivative groups include C1 to C30 alkyl, C2 to C30 alkenyl, C2 to C30 alkynyl, C6 to C30 aryl, C5 to C30 heteroaryl, C1 to C30 alkylamino, C6 to C30 arylamino, C6 to C30 heteroarylamino, C6 to C30 arylheteroarylamino, etc., but are not limited thereto.

[0070] Deuterium in the present invention refers to a stable isotope of hydrogen, also known as heavy hydrogen, and its element symbol is D.

[0071] As used herein, in "deuterated" or "undeuterated," the term "deuterated" means that at least one hydrogen in the group is re-coordinated with deuterium. The term "undeuterated" means that none of the hydrogens in the group are re-coordinated with deuterium.

[0072] m and p are each independently an integer of 0-7, which means that m and p can each independently be 0, 1, 2, 3, 4, 5, 6, or 7; k is an integer of 0-6, which means that k can be 0, 1, 2, 3, 4, 5, or 6; g is an integer of 0-4, which means that g can be 0, 1, 2, 3, or 4.

[0073] The aromatic group in the present invention refers to an all-carbon monocyclic or fused polycyclic group of 6 to 30 carbon atoms with a completely conjugated π electron system. Non-limiting examples of aromatic groups include phenyl, naphthyl, anthracenyl, biphenyl, o-terphenyl, m-terphenyl, p-terphenyl, triphenylenyl, triphenyl[1,12-bcd]furyl, and phenanthrenyl.

[0074] The "heteroaryl" herein refers to a heteroaryl group obtained by replacing one or more carbon atoms in the structure of "aryl" with one or more heteroatoms (such as N, O or S).

[0075] If the specific conditions are not specified in the examples, the experiments were carried out under conventional conditions or those recommended by the manufacturer. All reagents or instruments used, if the manufacturer is not specified, are commercially available conventional products.

[0076] Example 1:

[0077]

[0078] The synthesis method of compound 6 is as follows:

[0079]

[0080] To a 1L single-necked flask, 1-a (100 g, 0.332 mol, 1 eq), silver carbonate (18.33 g, 66.5 mmol, 0.2 eq), diphenylcyclohexylphosphine (44.54 g, 0.166 mol, 0.5 eq), deuterated water (132.8 g, 6.64 mol, 20 eq), and toluene (33.2 ml) were added. The mixture was heated to 120°C and stirred for 24 h. The reaction was stopped and filtered through silica gel. The filtrate was added with DCM and stirred to separate the layers. The aqueous phase was extracted with DCM, and the combined organic phases were concentrated to dryness under reduced pressure. The product was purified by column chromatography (rinsing with pure PE). The product was collected, concentrated to dryness under reduced pressure, and then further deuterated (recharging and post-processing according to the above-mentioned dosage) to obtain 83.5 g of 1-b as a colorless oil in an 82.8% yield.

[0081]

[0082] To a 2L three-necked flask were added 1-b (83.5g, 0.275mol, 1eq), 1-c (41.8g, 0.275mol, 1eq), potassium carbonate (76g, 0.55mol, 2eq), and toluene / ethanol / water (800ml + 400ml + 240ml). Under nitrogen protection, tetrakistriphenylphosphine palladium (6.36g, 5.5mmol, 0.02eq) was added and the reaction was stirred at reflux. HPLC monitoring of 1-b yielded ≤1%. The reaction was terminated, and 200ml of water was added with stirring to separate the liquids. The aqueous phase was extracted with DCM, and the combined organic phases were filtered through silica gel. The filtrate was concentrated to dryness under reduced pressure to afford intermediate 1-d, which was used directly in the next step without further purification.

[0083] To a 2L single-necked flask, add 1-d (theoretical 78.1g, 0.275mol, 1eq) and 800ml of DCM. The temperature was cooled to below 0°C, and boron tribromide (theoretical 207g, 0.825mol, 3eq) was added dropwise. After completion of the dropwise addition, the reaction was stirred at room temperature. HPLC monitoring indicated that 1-d ≤ 0.5%. The reaction was stopped, the temperature was lowered to below -10°C, and water was slowly added dropwise to quench the reaction. The mixture was stirred and separated. The aqueous phase was extracted with DCM. The organic phases were combined and washed twice with water with stirring. The organic phase was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness under reduced pressure to obtain intermediate 1-e, which was used directly in the next step without purification.

[0084] To a 2L single-necked flask, add intermediate 1-e (theoretical 74.3g, 0.275mol, 1eq), potassium carbonate (114g, 0.825mol, 1eq), and 700ml of DMF. The reaction was stirred at 150°C. HPLC monitoring was performed to determine if 1-e was ≤0.5%. The reaction was terminated, filtered while hot, and the filter cake rinsed with a small amount of DMF. The filtrate was added to 2000ml of water, stirred to allow crystallization, filtered, and the filter cake rinsed with water. The mixture was then slurried in 100ml of ethanol and allowed to cool for 2 hours to allow crystallization. The filter cake was then filtered and air-dried at 85°C to yield 46g of an off-white solid, 1-f, with a total yield of 66.9% across the three steps.

[0085]

[0086] Under nitrogen, a 1-L three-necked flask was charged with 1-f (46 g, 0.184 mol, 1 eq), 1-g (25.4 g, 0.1932 mol, 1.05 eq), sodium tert-butoxide (21.22 g, 0.2208 mol, 1.2 eq), tri-tert-butylphosphine (14.9 mL, 7.36 mmol, 0.04 eq), and toluene (500 mL). Trisdibenzylideneacetonepalladium (3.37 g, 3.68 mmol, 0.02 eq) was added under nitrogen. The reaction was heated to 110°C and stirred. HPLC monitoring confirmed that 1-f ≤1%. The reaction was terminated, and water was added with stirring to separate the liquids. The aqueous phase was extracted with DCM, and the combined organic phases were filtered through silica gel. The filtrate was concentrated to dryness under reduced pressure. 100 mL of ethanol was added, stirred at reduced temperature, and crystallized. The mixture was filtered and air-dried at 85°C to obtain 49.74 g of a gray-black solid, 1-h, in a yield of 89.9%.

[0087] Under N2 protection, 1-h (49.74 g, 0.165 mol, 1 eq), DBU (50.4 g, 0.331 mol, 2 eq), XPhos (7.87 g, 0.0165 mol, 0.1 eq) and DMAc (500 mL) were added to a 1 L three-necked flask. Under nitrogen protection, palladium acetate (1.85 g, 8.25 mmol, 0.02 eq) was added. The temperature was raised to 160°C and the reaction was stirred. The reaction temperature of 1-h was monitored by HPLC and the reaction temperature was ≤1%. The reaction was stopped, DMAc was removed by distillation under reduced pressure, 70 g of 100-200 mesh silica gel sand was added to the residue, and 700 g of 100-200 mesh silica gel was loaded into a column for column chromatography with PE / DCM = 10 / 1-5 / 1-3 / 1-2 / 1-1 / 1. The product was collected and concentrated under reduced pressure to near dryness. Petroleum ether was added, the mixture was filtered, and air-dried at 85° C. to obtain 30 g of an off-white solid 1-i, with a yield of 69.1%.

[0088]

[0089] Under N2 protection, 1-i (30 g, 0.114 mol, 1 eq), 1-j (39.2 g, 0.114 mol, 1 eq), sodium tert-butoxide (13.15 g, 0.1368 mol, 1.2 eq), tri-tert-butylphosphine (9.3 mL, 4.56 mmol, 0.04 eq) and toluene (300 mL) were added to a 1 L three-necked flask. Under nitrogen protection, trisdibenzylideneacetonepalladium (2.09 g, 2.28 mmol, 0.02 eq) was added. The temperature was raised to 110 ° C and the reaction was stirred. HPLC monitoring showed that 1-f ≤ 1%. The reaction was stopped, 200 ml of water and 500 ml of ethanol were added, the temperature was lowered and stirred to crystallize for 4 h, and the mixture was filtered. The filter cake was heated with toluene to dissolve it clearly and then filtered through silica gel while hot. An equal volume of ethanol was added to the filter cake, the temperature was lowered and stirred to crystallize, and the mixture was filtered. The filter cake was recrystallized from toluene / ethanol four times and then recrystallized once from pure toluene to obtain 39.8 g of off-white solid compound 6 with a yield of 61.2%.

[0090] The following compounds 1, 5, 10, 23, 24, 28, 36, 40, 42, 45, 55, 56, 65, 74 were obtained in a similar manner:

[0091] Table 1

[0092]

[0093]

[0094]

[0095]

[0096] The synthesis and identification results of the compounds prepared above are shown in Table 2 below:

[0097] Table 2

[0098]

[0099] Thermodynamic performance test:

[0100] The thermal gravimetric temperature Td and melting point temperature Tm of compounds 1, 5, 6, 10, 23, 24, 28, 36, 40, 42, 45, 55, 56, 65, and 74 in Examples 1-15 of the present invention were tested. The results are shown in Table 3:

[0101] Note: Thermogravimetric temperature (Td) is the temperature at which the weight loss is 5% in a nitrogen atmosphere, and was measured on a TGAN-1000 thermogravimetric analyzer with a nitrogen flow rate of 10 mL / min. The melting point (Tm) was determined by differential scanning calorimetry (DSC, Xinke DSC N-650) at a heating rate of 10°C / min.

[0102] Table 3:

[0103]

[0104] As can be seen from Table 3 above, the compounds of the present invention have relatively high Td and Tm values, indicating that they have excellent thermal stability. When applied to organic electroluminescent devices, they can effectively extend the service life of the organic electroluminescent devices and achieve better performance.

[0105] Device performance test:

[0106] Application Example 1:

[0107] ITO was used as the reflective layer anode substrate material, and its surface was treated with water, acetone, and N2 plasma in sequence;

[0108] On top of the ITO anode substrate, 10 nm of HT-1 doped with 5% NDP-9 was deposited to form a hole injection layer (HIL);

[0109] A hole transport layer (HTL) was formed by evaporating 100 nm of HT-1 on the hole injection layer (HIL);

[0110] GP was vacuum evaporated on the hole transport layer (HTL) to form a second hole transport layer (GPL) with a thickness of 10 nm;

[0111] Compound 6 prepared in Example 1 of the present invention and compound P-1 were co-evaporated at a ratio of 5:5 as the luminescent host material, and GD-1 was evaporated as a doping material (the amount of GD-1 was 8% of the total weight of compound 6 and P-1) on the second hole transport layer (GPL) to form a luminescent layer with a thickness of 20 nm;

[0112] HB-1 was evaporated onto the light-emitting layer to obtain a hole blocking layer (HBL) with a thickness of 20 nm;

[0113] ET-1 and LiQ were co-evaporated onto the hole blocking layer (HBL) in a ratio of 5:5 to obtain an electron transport layer (ETL) with a thickness of 30 nm;

[0114] Magnesium (Mg) and silver (Ag) were mixed in a ratio of 9:1 and evaporated onto the electron transport layer (ETL) to form an electron injection layer (EIL) with a thickness of 50 nm.

[0115] Silver (Ag) is then evaporated onto the electron injection layer to form a 100nm-thick cathode. A 50nm-thick layer of DNTPD is deposited on the cathode sealing layer. Furthermore, the cathode surface is sealed with a UV-curable adhesive and a seal cap containing a desiccant to protect the organic electroluminescent device from atmospheric oxygen or moisture. Thus, an organic electroluminescent device is prepared.

[0116]

[0117] Application Example 2-15

[0118] Compounds 1, 5, 6, 10, 23, 24, 28, 36, 40, 42, 45, 55, 56, 65, and 74 in Examples 2-15 of the present invention were used to replace Compound 6 in Application Example 1, respectively. Other parts were consistent with Application Example 1, and organic electroluminescent devices of Application Examples 2-15 were prepared accordingly.

[0119] Comparative Examples 1-3

[0120] The difference between Control Examples 1-3 and Application Example 1 is that Compound D1 in CN113429413A and Compounds D2 and D3 in KR1020230000949A are used to replace Compound 6 in Application Example 1, and the rest is the same as Application Example 1.

[0121] The organic electroluminescent devices prepared in Application Examples 1-15 and Comparative Examples 1-3 were tested respectively, and the test results are shown in Table 4.

[0122] Table 4

[0123]

[0124] As shown in Table 4 above, the application of the compound of the present invention in an organic electroluminescent device as a main material of the light-emitting layer can improve the luminous efficiency of the organic electroluminescent device to a certain extent, reduce the starting voltage, and relatively reduce power consumption.

[0125] The organic electroluminescent devices prepared in Control Examples 1-3 and Application Examples 1-10 were tested for luminescence lifetime, and the luminescence lifetime T97% data (the time it takes for the luminescence brightness to drop to 97% of the initial brightness) was obtained. The test equipment was a TEO light-emitting device lifetime test system. The results are shown in Table 5:

[0126] Table 5

[0127] Experimental group <![CDATA[Current density (mA / cm 2 )]]> T97％ Comparative Example 1 10 90％ Comparative Example 2 10 100％ Comparative Example 3 10 98％ Application Example 1 10 155％ Application Example 2 10 149％ Application Example 3 10 150％ Application Example 4 10 144％ Application Example 5 10 137％ Application Example 6 10 140％ Application Example 7 10 131％ Application Example 8 10 135％ Application Example 9 10 139％ Application Example 10 10 141％

[0128] As can be seen from Table 5 above, when the compound of the present invention is used as the main material of the light-emitting layer in an organic electroluminescent device, the service life of the organic electroluminescent device prepared is greatly improved, so it has a very broad application prospect.

[0129] The series of detailed descriptions listed above are only specific descriptions of feasible implementation methods of the present invention. They are not intended to limit the scope of protection of the present invention. Any equivalent implementation methods or changes that do not deviate from the technical spirit of the present invention should be included in the scope of protection of the present invention.

[0130] In addition, it should be understood that although this specification is described in terms of implementation methods, not every implementation method contains only one independent technical solution. This narrative method of the specification is only for the sake of clarity. Those skilled in the art should regard the specification as a whole. The technical solutions in each embodiment can also be appropriately combined to form other implementation methods that can be understood by those skilled in the art.

Claims

1. A compound, characterized in that Its structural formula is shown in Formula 1 below: X is O, S or Se; Ar1 and Ar2 are each independently selected from the following groups: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, spirobifluorenyl, 9,9-dimethylfluorenyl, each of which may be further substituted by one or more of deuterium, fluorine, cyano, C1-C10 alkyl, C1-C10 deuterated alkyl, C1-C10 cycloalkyl, C1-C10 deuterated cycloalkyl, C6-C30 aryl, C6-C30 deuterated aryl, C5-C30 heteroaryl, and C5-C30 deuterated heteroaryl; L1-L3 are each independently selected from a single bond, phenyl, biphenyl, and naphthyl, each of which may be further substituted with one or more of deuterium, fluorine, cyano, C1-C10 alkyl, C6-C18 aryl, and C5-C20 heteroaryl; A1-A6 are each independently selected from one or more of deuterium, fluorine, cyano, phenyl, biphenyl, naphthyl, and pyridyl, wherein A1-A6 contain at least one deuterium.

2. The compound according to claim 1, characterized in that Its structural formula is shown in Formula 2 below: X is O, S or Se; Ar1 and Ar2 are each independently selected from the following groups: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, pyridyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, spirobifluorenyl, 9,9-dimethylfluorenyl, each of which may be further substituted with deuterium, fluorine, cyano, deuterated or undeuterated phenyl, biphenyl, methyl, ethyl, tert-butyl, cyclopentyl, cyclohexyl or one or more thereof; L1-L3 are each independently selected from a single bond, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, and pyridyl.

3. The compound according to claim 1 or 2, characterized in that: X is O or S; Ar1 and Ar2 are each independently selected from the following groups: phenyl, biphenyl, terphenyl, pyridyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, spirobifluorenyl, 9,9-dimethylfluorenyl, each of which may be further substituted by deuterium, fluorine, cyano, deuterated or undeuterated groups: phenyl, biphenyl, methyl, ethyl, tert-butyl, cyclopentyl, cyclohexyl or one or more thereof; L1-L3 are each independently selected from a single bond, phenyl, deuterated phenyl, biphenyl, and deuterated biphenyl.

4. The compound according to claim 1, characterized in that Its structural formula is shown in Formula 3 below: X is O or S; Ar1 and Ar2 are each independently selected from the following groups: phenyl, biphenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, each of which may be further substituted with one or more of the following groups: phenyl, biphenyl, methyl, tert-butyl, deuterated or undeuterated; L1 and L2 are each independently selected from a single bond, a phenyl group, a deuterated phenyl group, a biphenyl group, and a deuterated biphenyl group.

5. The compound according to claim 1 or 4, characterized in that: X is O or S; Ar1 and Ar2 are each independently selected from the following groups: phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, each of which may be further substituted with one or more of deuterium, phenyl, deuterated phenyl, methyl, and tert-butyl; L1 and L2 are each independently selected from a single bond, a phenyl group, a deuterated phenyl group, a biphenyl group, and a deuterated biphenyl group.

6. The compound according to claim 1, characterized in that The compound is any one of the following compounds:

7. An organic electroluminescent device, characterized in that: The invention comprises a first electrode, a second electrode and an organic layer formed between the first electrode and the second electrode; the organic layer contains the compound according to any one of claims 1 to 6.

8. The organic electroluminescent device according to claim 7, characterized in that: The organic layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer; the light-emitting layer contains the compound according to any one of claims 1 to 6.

9. The organic electroluminescent device according to claim 8, wherein The light-emitting layer further comprises at least one of the following formula 5 or formula 6: in, Ar4 and Ar5 are each independently selected from the following substituted or unsubstituted groups: C6-C30 aryl, C5-C30 heteroaryl, and the substituents of Ar4 and Ar5 are selected from one or more of deuterium, fluorine, cyano, C1-C10 alkyl, C1-C10 deuterated alkyl, C1-C10 cycloalkyl, C1-C10 deuterated cycloalkyl, C6-C30 aryl, C6-C30 deuterated aryl, and C5-C30 heteroaryl; L4 and L5 are each independently selected from a single bond, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group, and the substituents of L4 and L5 are selected from one or more of deuterium, fluorine, cyano, C1-C10 alkyl, C6-C18 aryl, and C5-C20 heteroaryl groups; R2-R5 are each independently selected from hydrogen, deuterium, fluorine, cyano, deuterated or undeuterated groups: one or more of phenyl, biphenyl, methyl, ethyl, and tert-butyl; m and p are each independently an integer from 0 to 7; k is an integer from 0 to 6; g is an integer from 0 to 4.

10. The organic electroluminescent device according to claim 8 or 9, characterized in that: The light-emitting layer contains a light-emitting host material, which is a mixture of the compound according to any one of claims 1 to 6 and any one or more of compounds P-1 to P-88. Compounds P-1 to P-88 are as follows:

11. An electronic display device, characterized in that: Contains the organic electroluminescent device according to claim 7.

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