Compound and organic electroluminescent device

Abstract

According to the brand new organic electroluminescent material provided by the invention, benzofuro carbazole groups directly connected with triazine groups are all deuterated, so that the chemical stability, thermal stability and electron tolerance of the material are greatly improved, the interface stability of a device is further improved, interface defects are reduced, and the stability of the device is improved; and the service life of the device is greatly 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 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 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 represented by the combination of Formula 1 and Formula 2:

[0008]

[0009] X1 and X2 are each independently O, S or Se;

[0010] Ar1 is 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 groups selected from deuterium, fluorine, cyano, C1-C10 alkyl, C1-C10 deuterated alkyl, C1-C10 cycloalkyl, C1-C10 deuterated cycloalkyl, C6-C24 aryl, C6-C24 deuterated aryl, C5-C24 heteroaryl, C5-C24 deuterated heteroaryl;

[0011] L1 and L2 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] A is formula 2;

[0013] A 1- One of A8 is a linking site, and the rest are not linking sites. 1- A8 is independently selected from one or more of deuterium, fluorine, cyano, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, naphthyl, and pyridyl, wherein A1-A8 that are not linking sites contain at least one phenyl or deuterated phenyl group.

[0014] Preferably,

[0015] X1 and X2 are each independently O, S or Se;

[0016] Ar1 is 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 by deuterium, fluorine, cyano, deuterated or undeuterated groups: phenyl, biphenyl, methyl, ethyl, tert-butyl, cyclopentyl, cyclohexyl or one or more groups;

[0017] L1 and L2 are each independently selected from a single bond, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, and pyridyl;

[0018] A 1- One of A8 is a linking site, and the rest are not linking sites. 1- A8 is independently selected from one or more of deuterium, fluorine, cyano, phenyl, deuterated phenyl, biphenyl, and deuterated biphenyl, wherein A1-A8 that are not linking sites contain at least one phenyl or deuterated phenyl.

[0019] Preferably,

[0020] X1 and X2 are each independently O or S;

[0021] Ar1 is 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 groups;

[0022] L1 and L2 are each independently selected from a single bond, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl;

[0023] A 1- One of A8 is a linking site, and the rest are not linking sites. 1- A8 is independently selected from one or more of deuterium, phenyl, deuterated phenyl, biphenyl, and deuterated biphenyl, wherein A1-A8 that are not linking sites contain at least one phenyl or deuterated phenyl.

[0024] Preferably,

[0025] X1 and X2 are each independently O or S;

[0026] Ar1 is selected from the following groups: phenyl, biphenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, each of which may be further substituted with deuterium, deuterated or undeuterated phenyl, biphenyl, methyl, tert-butyl or one or more groups;

[0027] L1 and L2 are each independently selected from a single bond, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl;

[0028] A 1- One of A8 is a linking site, and the rest are not linking sites. 1- A8 is independently selected from one or more of deuterium, phenyl, deuterated phenyl, biphenyl, and deuterated biphenyl, wherein A1-A8 that are not linking sites contain at least one phenyl or deuterated phenyl.

[0029] More preferably,

[0030] X1 and X2 are each independently O or S;

[0031] Ar1 is selected from phenyl or biphenyl, each of which may be further substituted with one or more of deuterium, phenyl, deuterated phenyl, methyl, and tert-butyl;

[0032] L1 and L2 are each independently selected from a single bond, a phenyl group, and a deuterated phenyl group;

[0033] A 1-One of A8 is a linking site, and the rest are not linking sites. 1- A8 is independently selected from one or more of deuterium, phenyl, deuterated phenyl, biphenyl, and deuterated biphenyl, wherein A1-A8 that are not linking sites contain at least one phenyl or deuterated phenyl.

[0034] In a preferred embodiment, the compound of the present invention is any one of the following compounds:

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041] 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.

[0042] 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.

[0043] Furthermore, the light-emitting layer further contains at least one of the following formula 5 or formula 6:

[0044]

[0045] in,

[0046] 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;

[0047] 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;

[0048] 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;

[0049] m and p are each independently an integer from 0 to 7;

[0050] k is an integer from 0 to 6;

[0051] g is an integer from 0 to 4.

[0052] 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:

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060] An electronic display device comprising the organic electroluminescent device of the present invention.

[0061] An OLED lighting device comprising the organic electroluminescent device of the present invention.

[0062] The room temperature described in the present invention is 25±5°C.

[0063] As a further improvement of the present invention,

[0064] Compared with the prior art, the present invention has the following beneficial effects:

[0065] The present invention designs a new type of organic electroluminescent material with the following excellent properties:

[0066] 1. All the benzofuranocarbazole groups directly connected to the triazine group are deuterated, which greatly improves the chemical stability, thermal stability and electronic tolerance of the material, thereby improving the interface stability of the device, reducing interface defects, improving the stability of the device, and thus greatly improving the device life.

[0067] 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

[0068] Figure 1 A schematic structural diagram of an organic electroluminescent device provided by the present invention;

[0069] 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;

[0070] Figure 2 HPLC chart of compound 2 prepared in Example 1 of the present invention;

[0071] Figure 3 is the DSC spectrum of compound 2 prepared in Example 1 of the present invention, Figure 3 It can be seen that the melting point temperature Tm value of compound 2 is 272.63℃;

[0072] Figure 4 is the TGA spectrum of compound 2 prepared in Example 1 of the present invention, Figure 4 It can be seen that the thermal weight loss temperature Td value is 449.79℃; DETAILED DESCRIPTION

[0073] 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.

[0074] 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.

[0075] Deuterium in the present invention refers to a stable isotope of hydrogen, also known as heavy hydrogen, and its element symbol is D.

[0076] 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.

[0077] 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.

[0078] 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.

[0079] 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).

[0080] 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.

[0081] Example 1:

[0082]

[0083] The synthesis method of compound 2 is as follows:

[0084]

[0085] To a 1L single-necked flask, 1-a (70 g, 0.2721 mol, 1 eq) and deuterated benzene (458 g, 5.44 mol, 20 eq) were added dropwise, followed by the dropwise addition of trifluoromethanesulfonic acid (286 g, 1.905 mol, 7 eq). The mixture was heated to 50°C with stirring for 12 h. The reaction was stopped, cooled to below 0°C, and water was slowly added dropwise to quench the reaction. Solid precipitated and was filtered. The filter cake was rinsed with water and ethanol. After drying, the filter cake was dissolved in 500 ml of DCM. 100 g of 100-200 mesh silica gel was added, and 700 g of 100-200 mesh silica gel was loaded onto a column for column chromatography (PE / DCM = 10 / 1). The product was collected and concentrated to dryness under reduced pressure to obtain 56 g of an off-white solid 1-b.

[0086]

[0087] Under N2 protection, 1-b (56 g, 0.21 mol, 1 eq), 1-c (77.5 g, 0.335 mol, 1.6 eq) and ultra-dry THF (1 L) were added to a 2 L three-necked flask and cooled to -15 to -10 °C. Sodium tert-butoxide (50.5 g, 0.525 mol, 2.5 eq) was added in batches. After the addition was completed, the reaction was stirred and kept warm. The reaction was stopped when 1-b ≤ 2% was monitored by HPLC. 200 ml of water was added and stirred for 30 min. The mixture was filtered and the filter cake was boiled with toluene three times, each time beating for 2 h. The filter cake was filtered while hot and dried at 85 °C to obtain 58.9 g of intermediate 1-d with a yield of 60.7%.

[0088]

[0089] A three-necked flask was charged with 1-e (50 g, 177.6 mmol, 1 eq), 1-f (23 g, 181.2 mmol, 1.02 eq), potassium carbonate (61.4 g, 444 mmol, 2.5 eq), and toluene / ethanol / water (500 / 250 / 150 ml). Tetrakistriphenylphosphine palladium (4.11 g, 3.5 mmol, 0.02 eq) was added under nitrogen. After addition, the mixture was heated to 85°C with stirring for 7 h. HPLC monitoring of 1-e concentration ≤1% was performed. The phases were separated, and the aqueous phase was extracted twice with 100 ml of ethyl acetate. The combined organic phases were dried over anhydrous sodium sulfate and spin-dried to obtain the crude product. The mixture was then slurried in 100 ml of ethanol at 60°C for 2 h, cooled to room temperature, filtered, and dried to yield 41 g of solid 1-g (82% yield).

[0090] 1-g (48g, 170.5mmol, 1eq), 1,4-dioxane (288ml), and heavy water (101.7g, 5.11mol, 30eq) were added to a three-necked flask. Under N2 protection, trifluoromethanesulfonic anhydride (480g, 1.70mol, 10eq) was slowly added dropwise at room temperature while stirring and refluxing. After the addition, the temperature was raised to 105°C and stirred for 48 hours. The reaction mixture was cooled to room temperature and slowly introduced into a potassium carbonate aqueous solution (350g potassium carbonate + 1.5L water) several times. The mixture was extracted with 500ml of dichloromethane and dried over magnesium sulfate. The filtrate was sanded, passed through a column, and washed with pure PE. The solid product was spin-dried to obtain 20g of solid 1-h with a yield of 42%.

[0091] A three-necked flask was charged with 1-h (21.3 g, 79.6 mmol, 1 eq), pinacol diboron (24.3 g, 103.5 mmol, 1.3 eq), potassium acetate (21.6 g, 238.7 mmol, 3 eq), and 1,4-dioxane (210 ml). Under nitrogen protection, X-Phos (2.1 g, 4.8 mmol, 0.06 eq) and tris(dibenzylideneacetone)palladium (2.02 g, 2.4 mmol, 0.03 eq) were added. After addition, the mixture was heated to 105°C and stirred for 1.5 h. The reaction was terminated and the mixture was passed through silica gel while hot. The filtrate was then dried to a solid. 60 ml of ethanol was added to a slurry at 85°C for 1 h, cooled to room temperature, filtered, and dried to obtain 26 g of solid 1-i, a 93.8% yield.

[0092]

[0093] To a 1L three-necked flask, 1-d (28.6g, 62mmol, 1eq), 1-i (26g, 68.2mmol, 1.1eq), potassium carbonate (17.14g, 124mmol, 2eq), and THF / water (600ml + 100ml) were added. Under nitrogen protection, tetrakistriphenylphosphine palladium (1.43g, 1.24mmol, 0.02eq) was added. The mixture was heated to 75°C and stirred under reflux for 10-16h. HPLC monitoring indicated that 1-d ≤2%. The reaction was terminated, and the mixture was filtered while hot. The filter cake was rinsed with water and ethanol, air-dried at 85°C, and recrystallized five times from o-dichlorobenzene. The filter cake was filtered, rinsed with ethanol, and air-dried at 85°C to obtain 21g of an off-white solid, compound 2, in a yield of 49.8%.

[0094] In a similar manner, the following compounds 6, 9, 25, 27, 29, 31, 32, 39, 40, 41, 42, 45, 46, 52, 59, 63, 75, 97, 98, 101, 102, 105, 112, 117 were obtained:

[0095] Table 1

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102] The synthesis and identification results of the compounds prepared above are shown in Table 2 below:

[0103] Table 2

[0104]

[0105]

[0106] Thermodynamic performance test:

[0107] The thermal weight loss temperature Td and melting point temperature Tm of compounds 2, 6, 9, 25, 27, 29, 31, 32, 39, 40, 41, 42, 45, 46, 52, 59, 63, 75, 97, 98, 101, 102, 105, 112, and 117 in Examples 1 to 25 of the present invention were tested. The results are shown in Table 3:

[0108] 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.

[0109] Table 3:

[0110]

[0111]

[0112] 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.

[0113] Device performance test:

[0114] Application Example 1:

[0115] ITO was used as the reflective layer anode substrate material, and its surface was treated with water, acetone, and N2 plasma in sequence;

[0116] 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);

[0117] A hole transport layer (HTL) was formed by evaporating 100 nm of HT-1 on the hole injection layer (HIL);

[0118] GP was vacuum evaporated on the hole transport layer (HTL) to form a second hole transport layer (GPL) with a thickness of 10 nm;

[0119] Compound 2 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 the doping material (the amount of GD-1 was 8% of the total weight of compound 2 and P-1) on the second hole transport layer (GPL) to form a luminescent layer with a thickness of 20 nm;

[0120] HB-1 was evaporated onto the light-emitting layer to obtain a hole blocking layer (HBL) with a thickness of 20 nm;

[0121] 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;

[0122] 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.

[0123] 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.

[0124]

[0125] Application Example 2-25

[0126] Compounds 6, 9, 25, 27, 29, 31, 32, 39, 40, 41, 42, 45, 46, 52, 59, 63, 75, 97, 98, 101, 102, 105, 112, and 117 in Examples 2-25 of the present invention were used to replace Compound 2 in Application Example 1, respectively. Other parts were consistent with Application Example 1, and organic electroluminescent devices of Application Examples 2-25 were prepared accordingly.

[0127] Comparative Examples 1-3

[0128] The difference between Control Examples 1-3 and Application Example 1 is that Compounds D1 and D2 in CN114641479A and Compound D3 in KR1020230000949A are used to replace Compound 2 in Application Example 1, and the rest is the same as Application Example 1.

[0129] The organic electroluminescent devices prepared in Application Examples 1-25 and Comparative Examples 1-3 were tested respectively, and the test results are shown in Table 4.

[0130] Table 4

[0131]

[0132] 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.

[0133] The organic electroluminescent devices prepared in Control Examples 1-3 and Application Examples 1-12 were tested for luminescence lifetime to obtain T97% data (the time it takes for the luminescence brightness to drop to 97% of the initial brightness). The test equipment was a TEO light-emitting device lifetime test system. The results are shown in Table 5:

[0134] Table 5

[0135] Experimental group <![CDATA[Current density (mA / cm 2 )]]> T97％ Comparative Example 1 10 92％ Comparative Example 2 10 96％ Comparative Example 3 10 100％ Application Example 1 10 153％ Application Example 2 10 143％ Application Example 3 10 145％ Application Example 4 10 145％ Application Example 5 10 139％ Application Example 6 10 142％ Application Example 7 10 138％ Application Example 8 10 146％ Application Example 9 10 142％ Application Example 10 10 148％ Application Example 11 10 135％ Application Example 12 10 144％

[0136] 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.

[0137] 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.

Claims

1. A compound, characterized in that The structural formula is represented by the combination of formula 1 and formula 2: X1 and X2 are each independently O, S or Se; Ar1 is 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 groups selected from deuterium, fluorine, cyano, C1-C10 alkyl, C1-C10 deuterated alkyl, C1-C10 cycloalkyl, C1-C10 deuterated cycloalkyl, C6-C24 aryl, C6-C24 deuterated aryl, C5-C24 heteroaryl, C5-C24 deuterated heteroaryl; L1 and L2 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; A is formula 2; One of A1-A8 is a linking site, and the remaining A1-A8 that are not linking sites are independently selected from one or more of deuterium, fluorine, cyano, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, naphthyl, and pyridyl, wherein A1-A8 that are not linking sites contain at least one phenyl or deuterated phenyl group.

2. The compound according to claim 1, characterized in that: X1 and X2 are each independently O, S or Se; Ar1 is 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 by deuterium, fluorine, cyano, deuterated or undeuterated groups: phenyl, biphenyl, methyl, ethyl, tert-butyl, cyclopentyl, cyclohexyl or one or more groups; L1 and L2 are each independently selected from a single bond, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, and pyridyl; One of A1-A8 is a linking site, and the remaining A1-A8 that are not linking sites are independently selected from one or more of deuterium, fluorine, cyano, phenyl, deuterated phenyl, biphenyl, and deuterated biphenyl, wherein A1-A8 that are not linking sites contain at least one phenyl or deuterated phenyl group.

3. The compound according to claim 1, characterized in that: X1 and X2 are each independently O or S; Ar1 is 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 groups; L1 and L2 are each independently selected from a single bond, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl; A 1- One of A8 is a linking site, and the rest are not linking sites. 1- A8 is independently selected from one or more of deuterium, phenyl, deuterated phenyl, biphenyl, and deuterated biphenyl, wherein A1-A8 that are not linking sites contain at least one phenyl or deuterated phenyl.

4. The compound according to claim 1, characterized in that: X1 and X2 are each independently O or S; Ar1 is selected from the following groups: phenyl, biphenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, each of which may be further substituted with deuterium, deuterated or undeuterated phenyl, biphenyl, methyl, tert-butyl or one or more groups; L1 and L2 are each independently selected from a single bond, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl; A 1- One of A8 is a linking site, and the rest are not linking sites. 1- A8 is independently selected from one or more of deuterium, phenyl, deuterated phenyl, biphenyl, and deuterated biphenyl, wherein A1-A8 that are not linking sites contain at least one phenyl or deuterated phenyl.

5. The compound according to claim 1, characterized in that: X1 and X2 are each independently O or S; Ar1 is selected from phenyl or biphenyl, 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, and a deuterated phenyl group; A 1- One of A8 is a linking site, and the rest are not linking sites. 1- A8 is independently selected from one or more of deuterium, phenyl, deuterated phenyl, biphenyl, and deuterated biphenyl, wherein A1-A8 that are not linking sites contain at least one phenyl or deuterated phenyl.

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 as claimed in claim 7.

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