Organic electroluminescent compounds and light-emitting devices

Abstract

The present invention discloses an organic electroluminescent compound and a light-emitting device, wherein the organic electroluminescent compound has a structure as shown in formula (1). In the N-type compound structure provided by the present invention, the electron-rich group consisting of carbazole and the phenyl group connected thereto is substituted with deuterium. When used with a P-type compound having a deuterated core region, the chemical stability, photoelectric stability, and thermal stability of the light-emitting material structure can be effectively improved, thereby improving the stability and service life of the light-emitting device using the material. At the same time, the N-type compound of the present invention can form a good premix material with the P-type compound having a deuterated core region, exhibiting good P / N stability and mass production stability during the vapor deposition process. The formed premix material has a more balanced carrier mobility, thereby significantly improving the efficiency and service life of the device. #imgabs0#.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic electroluminescence, and in particular relates to organic electroluminescent compounds and light-emitting devices. Background Art

[0002] Organic electroluminescent devices generally include a cathode, an anode, and an organic layer arranged between the two. 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, and when the excitons jump back to the ground state, light is emitted.

[0003] In recent years, deuterated luminescent materials have been frequently used in organic electroluminescent devices. Different methods of introducing deuterium atoms into luminescent materials may have different effects on device performance. For example, if deuterium substitution does not occur at active sites or sites with high electron density on the material molecule, the material's stability may not meet expectations, thereby affecting the device's lifespan. Poor compatibility between the main luminescent materials in organic electroluminescent devices may result in inefficient energy transfer to the dopant material, thus affecting the luminous efficiency. At the same time, we have found that the P / N ratio of current green light-emitting main luminescent materials varies significantly with increasing evaporation time, resulting in large fluctuations in device performance, poor stability, and low yield. Summary of the Invention

[0004] The technical purpose of the present invention is to develop organic electroluminescent materials with better performance.

[0005] In order to achieve the above technical objectives, the present invention provides the following technical solutions:

[0006] An organic electroluminescent compound, characterized in that the structural formula is as shown in the following formula (1):

[0007] Formula (1)

[0008] Where:

[0009] R0-R7 each independently represent deuterium, deuterium-substituted or unsubstituted C6-C30 aryl, provided that at least seven of R0-R7 are deuterium;

[0010] R8-R 11 Each independently represents hydrogen, deuterium, or a C6-C30 aryl group substituted or unsubstituted with deuterium, provided that R8-R 11 At least one of them is deuterium;

[0011] L1 and L2 each independently represent a single bond;

[0012] Ar1 and Ar2 are the same or different and represent a C6-C30 aryl group which is substituted or unsubstituted with a substituent, provided that when R0-R 11 When any one of Ar1 and Ar2 is not a deuterated or unsubstituted C6-C30 aryl group, at least one of Ar1 and Ar2 is a substituted or unsubstituted biphenyl group; the substituents of Ar1 and Ar2 are each independently selected from deuterium, cyano, C6-C20 aryl, deuterated C6-C20 aryl, C5-C20 heteroaryl, C1-C4 straight or branched alkyl, deuterated C1-C4 straight or branched alkyl, or a combination of more than one.

[0013] Furthermore, Ar1 and Ar2 are the same or different and represent phenyl or biphenyl groups which are substituted or unsubstituted, and the substituents of Ar1 and Ar2 are independently selected from one or more of deuterium, methyl, phenyl, deuterated methyl, and deuterated phenyl.

[0014] Furthermore, in the compound, R8-R 11 Medium, R8 or R 10 is a deuterium-substituted or unsubstituted C6-C30 aryl group, and at least one of the other three R groups is deuterium.

[0015] Furthermore, in the compound, seven R groups among R0-R7 are deuterium, and another non-deuterium group is phenyl or deuterated phenyl.

[0016] As a preferred embodiment, the compound of the present invention is selected from at least one of the following compounds:

[0017]

[0018] An organic electroluminescent device, characterized in that it 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 organic electroluminescent compound described in any one of the above items.

[0019] As a preferred embodiment, the organic layer includes a hole injection layer, a first hole transport layer, a second hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer, and the light-emitting layer contains any of the above organic electroluminescent compounds.

[0020] Furthermore, in the organic electroluminescent device, the light-emitting layer contains a light-emitting host material, and the light-emitting host material is composed of a first compound and a second compound. The first compound is any of the organic electroluminescent compounds described above, and the structure of the second compound is shown in the following formula (2-1) or formula (2-2):

[0021] Formula (2-1)

[0022] Formula (2-2)

[0023] Where:

[0024] L3, L4, L5 and L6 each independently represent a single bond, or a deuterium-substituted or unsubstituted C6-C20 arylene group;

[0025] Ar5, Ar6, Ar3 and Ar4 each independently represent a C6-C30 aryl group which may be substituted or unsubstituted, or a C5-C30 heteroaryl group which may be substituted or unsubstituted; the substituents of Ar5, Ar6, Ar3 and Ar4 are each independently selected from deuterium, or a C6-C20 aryl group which may be substituted or unsubstituted with deuterium;

[0026] R 12 and R 13 is deuterium, m1 represents an integer from 0 to 3, m2 is an integer selected from 0 to 4, and n represents an integer from 0 to 4.

[0027] Furthermore, in the second compound, L3, L4, L5 and L6 are each independently a single bond, a phenylene group or a deuterated phenylene group; Ar5, Ar6, Ar3 and Ar4 are each independently a substituted or unsubstituted phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylenyl group or an N-containing heteroaryl group, and the substituents of Ar5, Ar6, Ar3 and Ar4 are selected from one or more of deuterium, phenyl and deuterated phenyl groups.

[0028] Preferably, the second compound is selected from any one of the following compounds:

[0029]

[0030] The beneficial effects of the present invention are:

[0031] 1) In the structure of the N-type compound of the present invention, the electron-rich group consisting of carbazole and the benzene ring connected to it is substituted with deuterium. When used with the P-type compound with deuterium substituted in the core region (HOMO electron distribution region), the chemical stability, photoelectric stability and thermal stability of the luminescent material structure can be effectively improved, thereby improving the stability and service life of the light-emitting device using the material.

[0032] 2) The N-type compound of the present invention can form a good premix material with the deuterated P-type compound in the core region (HOMO electron distribution region), with good P / N stability and mass production stability during the evaporation process. The formed premix material has a more balanced carrier mobility, thereby significantly improving the efficiency and life of the device.

[0033] 3) The compound of the present invention has good solubility, which can reduce the material preparation cost and the mask cleaning cost. BRIEF DESCRIPTION OF THE DRAWINGS

[0034] Figure 1 This is a schematic structural diagram of the organic electroluminescent device provided by the present invention;

[0035] Figure 2 is the HPLC chromatogram of compound N-1 of the present invention;

[0036] Figure 3 is the HPLC chromatogram of compound N-3 of the present invention;

[0037] Figure 4 is the HPLC chromatogram of compound N-60 of the present invention;

[0038] Figure 1 The reference numerals in the figures represent: 1-anode, 2-hole injection layer, 3-first hole transport layer, 4-second hole transport layer, 5-light-emitting layer, 6-hole blocking layer, 7-electron transport layer, 8-electron injection layer, 9-cathode. DETAILED DESCRIPTION

[0039] The following further illustrates and describes embodiments of various aspects of the present invention. It should be understood that the following description is not intended to limit the claims to the specific aspects described. On the contrary, it is intended to cover alternatives, modifications, and equivalents that may be included within the scope defined by the appended claims.

[0040] As used herein, the terms "substituted" or "unsubstituted" refer to the realignment of at least one hydrogen atom of a group with a substituent group, such as deuterium, an aryl group, or a heteroaryl group. "Aryl" herein refers to a group containing one or more aromatic rings, including but not limited to benzene, naphthalene, phenanthrene, fluorene, and acenaphthene. "Heteroaryl" herein refers to a heteroaryl group in which one or more carbon atoms in the structure of an "aryl" group are replaced by one or more heteroatoms. The terms "C6-C30," "C5-C30," "C1-C4," "C6-C20," and "C5-C20" herein indicate that the modified group contains 6-30, 5-30, 1-4, 6-20, and 5-20 carbon atoms, respectively. "Deuterium" herein refers to a stable isotope of hydrogen, also known as heavy hydrogen, with the element symbol D.

[0041] 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.

[0042] Example 1:

[0043]

[0044] The synthesis method of compound N-1 is as follows:

[0045]

[0046]

[0047] Step 1: Under air atmosphere, 3-bromo-4-fluorobiphenyl (25 g, 0.1 mol, 1 eq), 25 ml of toluene, heavy water (40 g, 2 mol, 20 eq), silver carbonate (5.6 g, 0.02 mol, 20% eq), diphenylcyclohexylphosphine (13.41 g, 0.05 mol, 50% eq), and potassium carbonate (36 g, 0.26 mol, 1 eq) were added to a reaction flask. After the addition was complete, the reaction solution was heated to 120°C and reacted for 24 h. 150 ml of toluene was added to the reaction solution, the layers were separated, and the organic phase was concentrated to dryness. Column chromatography was performed to obtain approximately 21.5 g of intermediate 1 in an 85% yield.

[0048] Step 2: Under nitrogen protection, deuterated carbazole (14.87 g, 0.085 mol, 1 eq), intermediate 1 (21.5, 0.085 mol, 1 eq), 200 ml of DMF, and cesium carbonate (69 g, 0.2125 mol, 2.5 eq) were added to the reaction flask. After the addition was complete, the reaction solution was heated and refluxed for 12 h. The reaction was sampled and tested for completion by HPLC. After cooling, 200 ml of water was added for washing, and the product was filtered. After drying the filter cake, it was purified by petroleum ether / dichloromethane column chromatography to obtain approximately 27.74 g of intermediate 2, with a yield of 80%;

[0049] Step 3: Under nitrogen protection, intermediate 2 (27.84 g, 0.068 mol, 1 eq) was added to the reaction flask, and 300 ml of ultra-dry tetrahydrofuran was added. The temperature was cooled to -78°C, and 2.5 M n-butyl lithium (28.56 ml, 0.0714 mol, 1.05 eq) was added dropwise. After the addition was complete, the reaction was kept warm for 1 h, and triisopropyl borate (15.34 g, 0.0816 mol, 1.2 eq) was added dropwise. After the addition was complete, the temperature was naturally raised to room temperature, and saturated aqueous ammonium chloride was added. The layers were separated, and the organic phase was concentrated to dryness and recrystallized from ethyl acetate to obtain approximately 20.34 g of intermediate 3, with a yield of 80%;

[0050] Step 4: Under nitrogen protection, intermediate 3 (20.34 g, 0.0544 mol, 1 eq), triazine compound (14.5 g, 0.0544 mol, 1 eq), 300 ml of toluene, 150 ml of ethanol, potassium carbonate (18.63 g, 0.135 mol, 2.5 eq), and Pd(PPh3)4 (0.62 g, 0.00054 mol, 1% eq) were added to the reaction flask. After the addition was complete, the reaction solution was heated and refluxed overnight. The completion of the reaction was detected by HPLC sampling. The reaction solution was cooled, washed with water, separated, and the organic phase was passed through silica gel, concentrated to dryness, and subjected to column chromatography to obtain approximately 19.87 g of compound N-1, with a yield of 65%.

[0051] Other compounds were prepared by similar preparation methods, as shown in Table 1-1, Table 1-2, Table 1-3, Table 1-4, Table 1-5, Table 1-6, Table 1-7, Table 1-8, Table 1-9, Table 1-10, Table 1-11, Table 1-12, Table 1-13, Table 1-14, Table 1-15, Table 1-16, Table 1-17, Table 1-18, Table 1-19, Table 1-20, Table 1-21, Table 1-22, and Table 1-23:

[0052] Table 1-1

[0053]

[0054] Table 1-2

[0055]

[0056] Table 1-3

[0057]

[0058] Table 1-4

[0059]

[0060] Table 1-5

[0061]

[0062] Table 1-6

[0063]

[0064] Table 1-7

[0065]

[0066] Table 1-8

[0067]

[0068] Table 1-9

[0069]

[0070] Table 1-10

[0071]

[0072] Table 1-11

[0073]

[0074] Table 1-12

[0075]

[0076] Table 1-13

[0077]

[0078] Table 1-14

[0079]

[0080] Table 1-15

[0081]

[0082] Table 1-16

[0083]

[0084] Table 1-17

[0085]

[0086] Table 1-18

[0087]

[0088] Table 1-19

[0089]

[0090] Table 1-20

[0091]

[0092] Table 1-21

[0093]

[0094] Table 1-22

[0095]

[0096] Table 1-23

[0097]

[0098] The synthetic identification results of the compounds prepared in Table 1-1, Table 1-2, Table 1-3, Table 1-4, Table 1-5, Table 1-6, Table 1-7, Table 1-8, Table 1-9, Table 1-10, Table 1-11, Table 1-12, Table 1-13, Table 1-14, Table 1-15, Table 1-16, Table 1-17, Table 1-18, Table 1-19, Table 1-20, Table 1-21, Table 1-22, and Table 1-23 are shown in Table 2 below:

[0099] Table 2

[0100] Compound FD-Quality Compound FD-Quality N-1 m / z=561.26(C39H15D11N4=561.28) N-185 m / z= 637.25(C45H19D11N4= 637.32) N-3 m / z=637.31(C45H19D11N4=637.32) N-186 m / z= 637.30(C45H19D11N4= 637.27) N-4 m / z=642.34(C45H14D16N4=642.35) N-189 m / z= 642.29(C45H14D16N4=642.35) N-5 m / z=636.31(C45H20D10N4=636.32) N-192 m / z=637.30(C45H19D11N4=637.32) N-7 m / z=712.32 (C51H24D10N4=712.34) N-201 m / z=567.28(C39H9D17N4=567.32) N-10 m / z=646.38(C45H10D20N4=646.37) N-206 m / z=642.29(C45H14D16N4=642.35) N-17 m / z=641.37(C45H15D15N4=641.34) N-222 m / z=642.30(C45H14D16N4= 642.35) N-30 m / z=651.38(C45H5D25N4=651.40) N-229 m / z=642.31(C45H14D16N4=642.35) N-36 m / z=712.30(C51H24D10N4=712.34) N-235 m / z=576.35(C39D26N4=576.38) N-38 m / z=576.35(C39D26N4=576.38) N-236 m / z=656.40(C45D30N4=656.44) N-40 m / z=646.34(C45H10D20N4=646.37) N-244 m / z=656.47(C45D30N4=656.44) N-49 m / z=656.39(C45D30N4=656.44) N-253 m / z=576.35(C39D26N4=576.38) N-57 m / z=636.30(C45H20D10N4=636.31) N-259 m / z=576.32(C39D26N4=576.38) N-59 m / z=712.33(C51H24D10N4= 712.34) N-262 m / z=656.40(C45D30N4=656.44) N-60 m / z=636.30(C45H20D10N4=636.31) N-267 m / z=566.29(C39H10D16N4=566.32) N-68 m / z=717.35(C51H19D15N4=717.37) N-269 m / z=642.30(C45H14D16N4=642.35) N-72 m / z=646.38(C45H10D20N4=646.37 ) N-307 m / z=722.32(C51H14D20N4=722.40 ) N-73 m / z=647.31(C45H9D21N4=647.38 ) N-313 m / z=636.28(C45H20D10N4=636.31) N-77 m / z=636.27(C45H20D10N4=636.31 ) N-315 m / z=635.25(C45H21D9N4=635.30) N-79 m / z=712.30(C51H24D10N4=712.34 ) N-320 m / z=635.25(C45H21D9N4=635.30) N-83 m / z=717.34(C51H19D15N4=717.37 ) N-328 m / z=636.29(C45H20D10N4=636.31) N-96 m / z=656.39(C45D30N4=656.44 ) N-329 m / z=635.24(C45H21D9N4=635.30) N-97 m / z=722.38(C51H14D20N4= 722.40) N-337 m / z=636.25(C45H20D10N4=636.31) N-109 m / z=731.54(C51H5D29N4=731.46 ) N-339 m / z=635.19(C45H21D9N4=635.30) N-113 m / z=736.45(C51D34N4=736.49) N-345 m / z=635.39(C45H21D9N4=635.30) N-115 m / z=561.20(C39H15D11N4=561.28 ) N-347 m / z=634.42(C45H22D8N4=634.30) N-117 m / z=637.41(C45H19D11N4=637.32) N-351 m / z=634.27(C45H22D8N4=634.30) N-119 m / z=637.30(C45H19D11N4=637.32) N-353 m / z=635.14(C45H21D9N4=635.30) N-120 m / z=636.28(C45H20D10N4=636.31 ) N-359 m / z=634.08(C45H22D8N4=634.30) N-130 m / z=636.30(C45H20D10N4=636.31) N-361 m / z=635.19(C45H21D9N4=635.30 ) N-140 m / z=636.21(C45H20D10N4=636.31) N-363 m / z=634.21(C45H22D8N4=634.30) N-143 m / z=712.37(C51H24D10N4=712.34) N-372 m / z=636.40(C45H20D10N4=636.31) N-160 m / z=712.29(C51H24D10N4=712.34) N-379 m / z=635.24(C45H21D9N4=635.30) N-162 m / z=712.30(C51H24D10N4=712.34 ) N-387 m / z=636.15(C45H20D10N4=636.31) N-165 m / z=562.18(C39H14D12N4=562.29 ) N-396 m / z=626.27(C45H20D10N4=636.31) N-167 m / z=561.25(C39H15D11N4=561.28) N-398 m / z=635.41(C45H21D9N4=635.30) N-170 m / z=637.30(C45H19D11N4=637.32) N-404 m / z=635.25(C45H21D9N4=635.30) N-175 m / z=561.20(C39H15D11N4=561.28) N-410 m / z=634.17(C45H22D8N4=634.30) N-177 m / z=637.30(C45H19D11N4=637.32) N-412 m / z=635.33(C45H21D9N4=635.30) N-182 m / z=642.27(C45H14D16N4=642.35 ) N-418 m / z=634.22(C45H22D8N4=634.30 ) N-183 m / z=561.17(C39H15D11N4=561.28) N-422 m / z=634.11(C45H22D8N4=634.30)

[0101] Device performance test:

[0102] Application Example 1:

[0103] ITO was used as the reflective layer anode substrate material, and water, acetone, N 2Plasma treatment was performed on the surface of the substrate; 10 nm of HT-1 doped with 5% NDP-9 was deposited on the ITO anode substrate to form a hole injection layer (HIL); 100 nm of HT-1 was evaporated on the hole injection layer (HIL) to form a first hole transport layer (HTL); GP-1 was vacuum evaporated on the first hole transport layer (HTL) to form a second hole transport layer (GPL) with a thickness of 10 nm; Compound N-1 (N-type) and Compound P-19 (P-type) prepared in Example 1 of the present invention were co-evaporated in a ratio of 5:5 as light-emitting host materials, and GD-1 was evaporated as a doping material (the amount of GD-1 was 8% of the total weight of Compound N-1 and P-19) on the second hole transport layer (GPL) to form a 20 nm thick light-emitting layer; HB-1 was evaporated on the light-emitting layer to form a 20 nm thick hole blocking layer (HBL); ET-1 and LiQ are co-evaporated onto the hole blocking layer (HBL) in a ratio of 5:5 to obtain a 30nm thick electron transport layer (ETL); magnesium (Mg) and silver (Ag) are mixed and evaporated onto the electron transport layer (ETL) in a ratio of 9:1 to form a 50nm thick electron injection layer (EIL); silver (Ag) is then evaporated onto the electron injection layer to form a 100nm thick cathode, and a 50nm thick DNTPD is deposited on the cathode sealing layer. In addition, the cathode surface is sealed with a UV-curable adhesive and a seal cap containing a desiccant to protect the organic electroluminescent device from being affected by oxygen or moisture in the atmosphere. Thus, an organic electroluminescent device is prepared.

[0104] The structural formulas of the compounds used in each application example are as follows:

[0105]

[0106] Application Example 2-82:

[0107] Compounds N-3, N-4, N-5, N-7, N-10, N-17, N-30, N-36, N-38, N-40, N-49, N-57, N-59, N- 60. N-68, N-72, N-73, N-77, N-79, N-83, ​​N-96, N-97, N-109, N-113, N-115, N-117, N-1 19. N-120, N-130, N-140, N-143, N-160, N-162, N-165, N-167, N-170, N-175, N-177, N -182, N-183, N-185, N-186, N-189, N-192, N-201, N-206, N-222, N-229, N-235, N-236 , N-244, N-253, N-259, N-262, N-267, N-269, N-307, N-313, N-315, N-320, N-328, N-3 29. N-337, N-339, N-345, N-347, N-351, N-353, N-359, N-361, N-363, N-372, N-379, N -387, N-396, N-398, N-404, N-410, N-412, N-418, and N-422 respectively replace the compound N-1 in the application example, and are evaporated together with the P-type compound P-19 or P-40 as the light-emitting main material of the green light device. Under the same conditions as in application example 1, the organic electroluminescent device of application example 2-82 is produced accordingly.

[0108] Comparative Examples 1-5:

[0109]

[0110] The compound N-1 in the application example was replaced by the control compounds D-1, D-2, D-3, D-4, and D-5, respectively, and evaporated with the compound P-19 or P-40 as the main luminescent material of the green light device. Under the same conditions as in application example 1, the organic electroluminescent devices of control examples 1-5 were prepared.

[0111] At a current density of 10 mA / cm 2 The characteristics of the organic electroluminescent device manufactured in the application example and the organic electroluminescent device manufactured in the control example were tested under the conditions of , and the test results are shown in the following Table 3-1, Table 3-2, Table 3-3, Table 3-4, and Table 3-5:

[0112] Table 3-1

[0113]

[0114] Table 3-2

[0115]

[0116] Table 3-3

[0117]

[0118] Table 3-4

[0119]

[0120] Table 3-5

[0121]

[0122] It can be seen from Table 3-1, Table 3-2, Table 3-3, Table 3-4, and Table 3-5 that at the same current density, the N-type compound provided by the present invention is applied to an organic electroluminescent device, and is combined with a P-type compound with deuteration in the core region. Compared with the existing compounds, the luminous efficiency of the device is significantly improved, the starting voltage of the device is reduced to varying degrees, and the power consumption of the device is relatively reduced.

[0123] The organic electroluminescent devices prepared in the control examples 1-5 and some application examples were tested for luminescence life. 2 Under the test conditions, the luminous lifetime T97% data (the time it takes for the luminous brightness to drop to 97% of the initial brightness) is obtained. The test results are shown in Table 4 (with the lifetime data of Control Example 1 as a reference):

[0124] Table 4

[0125]

[0126] As can be seen from the above table, the N-type compound provided by the present invention and the comparative compound are applied to the organic electroluminescent device in the same manner. Under the same parameters such as current density, the service life of the device in the application example of the present invention is greatly improved compared with the comparative example.

[0127] Table 5. HPLC chromatographic data of compounds N-1, N-3, and N-60 of the present invention

[0128]

[0129] It should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention and are not intended to limit the present invention. Although the present invention has been described in detail with reference to the preferred embodiments, those skilled in the art should understand that the technical solutions of the present invention may be modified or replaced by equivalents without departing from the spirit and scope of the technical solutions of the present invention, which should all be included in the scope of the claims of the present invention.

Claims

1. An organic electroluminescent compound, characterized in that Any one selected from the following compounds: 。 2. An organic electroluminescent device, characterized in that: The 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 organic electroluminescent compound according to claim 1.

3. The organic electroluminescent device according to claim 2, wherein: The organic layer includes a hole injection layer, a first hole transport layer, a second hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer, and the light emitting layer contains the organic electroluminescent compound according to claim 1.

4. The organic electroluminescent device according to claim 3, wherein The light-emitting layer contains a light-emitting host material, which is composed of a first compound and a second compound. The first compound is the organic electroluminescent compound according to the claim, and the structure of the second compound is shown in the following formula (2-1) or formula (2-2): Formula (2-1) Formula (2-2) Where: L3, L4, L5 and L6 each independently represent a single bond, or a deuterium-substituted or unsubstituted C6-C20 arylene group; Ar5, Ar6, Ar3 and Ar4 each independently represent a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C5-C30 heteroaryl group; the substituents of Ar5, Ar6, Ar3 and Ar4 are each independently selected from deuterium, a deuterated or unsubstituted C6-C20 aryl group; R 12 and R 13 is deuterium, m1 is selected from an integer within the range of 0-3, m2 is selected from an integer within the range of 0-4, and n is selected from an integer within the range of 0-4.

5. The organic electroluminescent device according to claim 4, wherein: L3, L4, L5 and L6 are each independently a single bond, a phenylene group or a deuterated phenylene group; Ar5, Ar6, Ar7 and Ar8 are each independently a substituted or unsubstituted phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylenyl group or an N-containing heteroaryl group, and the substituents of Ar5, Ar6, Ar3 and Ar4 are selected from one or more of deuterium, phenyl and deuterated phenyl groups.

6. The organic electroluminescent device according to claim 4, wherein: The second compound is selected from any one of the following compounds: 。

Images