Organic electroluminescent compound and light-emitting device

By using deuterium-substituted N-type compounds in organic electroluminescent devices and deuterated P-type compounds in core regions, the problem of large changes in the P/N ratio after the evaporation time of green light host luminescent materials in the prior art is solved, and the stability and service life of the device are improved.

CN120081828AActive Publication Date: 2025-06-03NANJING TOPTO MATERIALS CO LTD

Patent Information

Application Number
CN202510579667.X
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2025-05-07
Publication Date
2025-06-03
Estimated Expiration
2045-05-07

AI Technical Summary

Technical Problem

After the evaporation time of the green-light main luminescent material of existing organic electroluminescent devices has a large change in the P/N ratio, resulting in large fluctuations in device performance, poor stability and low yield.

Method used

A new organic electroluminescent compound was developed in which the carbazole of the N-type compound and the benzene ring attached to it were replaced by deuterium and paired with the deuterated P-type compound in the core region to form a good Premix material.

Benefits of technology

Through the deuterium-substituted compound structure, the chemical stability, photoelectric stability and thermal stability of the luminescent materials are improved, thereby improving the stability and service life of the device and reducing the preparation cost.

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Abstract

The invention discloses an organic electroluminescent compound and a luminescent device. The organic electroluminescent compound has a structure as shown in a formula (1). In the structure of the N-type compound provided by the invention, an electron-rich group formed by carbazole and phenyl connected with the carbazole is substituted by deuterium, and the deuterated P-type compound in the core region is matched, so that the chemical stability, photoelectric stability and thermal stability of the structure of the luminescent material can be effectively improved, the stability of a luminescent device using the material is further improved, and the service life of the luminescent device is prolonged; meanwhile, the N-type compound and the deuterated P-type compound in the core area can form a good Premix material, good P / N stability and mass production stability are achieved in the evaporation process, the formed Premix material has more balanced carrier mobility, the efficiency of a device is greatly improved, and the service life of the device is greatly prolonged. And # imgabs0 #.
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Description

Technical Field

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

[0002] An organic electroluminescent device generally includes a cathode, an anode, and an organic layer disposed therebetween. 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 holes and electrons meet, excitons are formed, and light is emitted when the excitons return to the ground state.

[0003] In recent years, deuterated luminescent materials have often been applied in organic electroluminescent devices. Luminescent materials with deuterium atoms introduced in different ways may have different effects on the performance of the devices. For example, if deuteration does not occur at the active sites and sites with high electron density of the material molecules, it may lead to the material stability not meeting the expectations, thereby affecting the device life; the poor compatibility between the host materials of the organic electroluminescent device may result in inefficient energy transfer to the doped material, thus affecting the luminous efficiency, etc. At the same time, we found that for the current green host luminescent materials, with the extension of the evaporation time, the P / N ratio changes greatly, resulting in large fluctuations in device performance, poor stability, and low yield. Summary of the Invention

[0004] The technical object of the present invention is to develop organic electroluminescent materials with more excellent performance.

[0005] To achieve the above technical object, the present invention provides the following technical solutions: An organic electroluminescent compound, characterized in that the structural formula is as shown in formula (1): Formula (1) In the formula: R 0 -R 7 each independently represents deuterium, a C6-C30 aryl group substituted or unsubstituted with deuterium, provided that at least seven of R 0 -R 7 are deuterium; R 8 -R 11 each independently represents hydrogen, deuterium, a C6-C30 aryl group substituted or unsubstituted with deuterium, provided that at least one of R 8 -R 11 is deuterium; L 1 and L 2 each independently represents a single bond; Ar 1 and Ar 2Same or different, representing a C6-C30 aryl group which may or may not be substituted by substituents, provided that when any one of R 0 -R 11 is not a C6-C30 aryl group which may or may not be deuterium-substituted, at least one of Ar 1 and Ar 2 is a biphenyl group which may or may not be substituted by substituents; the substituents of Ar 1 and Ar 2 are each independently selected from one or more of deuterium, cyano group, C6-C20 aryl group, deuterated C6-C20 aryl group, C5-C20 heteroaryl group, C1-C4 straight-chain or branched alkyl group, deuterated C1-C4 straight-chain or branched alkyl group, or a combination of multiple ones.

[0006] Furthermore, Ar 1 and Ar 2 same or different, represent a phenyl group or a biphenyl group which may or may not be substituted by substituents, and the substituents of Ar 1 and Ar 2 are each independently selected from one or more of deuterium, methyl group, phenyl group, deuterated methyl group, deuterated phenyl group.

[0007] Furthermore, in the said compound, in R 8 -R 11 , R 8 or R 10 is a C6-C30 aryl group which may or may not be deuterium-substituted, and at least one of the remaining three R groups is deuterium.

[0008] Furthermore, in the said compound, the seven R groups in R 0 -R 7 are deuterium, and the other non-deuterium group is a phenyl group or a deuterated phenyl group.

[0009] As a preferred embodiment, the compounds of the present invention are selected from at least one of the following compounds:

[0010] 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, and the organic layer contains the organic electroluminescent compound described in any one of the above.

[0011] 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 the organic electroluminescent compound described in any one of the above.

[0012] 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 the organic electroluminescent compound described in any one of the above, 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) In the formula: L 3 、L 4 、L 5 and L 6 each independently represent a single bond, or a C6-C20 arylene group which is deuterium-substituted or unsubstituted; Ar 5 、Ar 6 、Ar 3 and Ar 4 each independently represent a C6-C30 aryl group which is substituted or unsubstituted by a substituent, or a C5-C30 heteroaryl group which is substituted or unsubstituted by a substituent; Ar 5 、Ar 6 、Ar 3 and Ar 4 substituents of are each independently selected from deuterium, or a C6-C20 aryl group which is deuterium-substituted or unsubstituted; R 12 and R 13 are deuterium, m1 represents an integer from 0 to 3, m2 is selected from integers from 0 to 4, and n represents an integer from 0 to 4.

[0013] Further, in the second compound, L 3 、L 4 、L 5 and L 6 each independently are a single bond, a phenylene group or a deuterated phenylene group; Ar 5 、Ar 6 、Ar 3 and Ar 4 each independently are a substituted or unsubstituted phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a benzo[a]phenanthryl group or a N-containing heteroaryl group, Ar 5 、Ar 6 、Ar 3 and Ar 4 substituents of are selected from one or more of deuterium, a phenyl group and a deuterated phenyl group.

[0014] Preferably, the second compound is selected from any one of the following compounds:

[0015] The beneficial effects of the present invention are as follows: 1) In the N-type compound structure of the present invention, the electron-rich group composed of carbazole and the benzene ring connected thereto is replaced by deuterium, and is paired with the deuterated P-type compound in the core region (HOMO electron distribution region), which can effectively improve the chemical stability, optoelectronic stability and thermal stability of the luminescent material structure, and further improve the stability and service life of the light-emitting device using this material.

[0016] 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), 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.

[0017] 3) The compound of the present invention has good solubility, which can reduce the preparation cost of the material and the cleaning cost of the mask. Description of the Drawings

[0018] Figure 1 is a schematic structural diagram of the organic electroluminescent device provided by the present invention; Figure 2 is the HPLC chromatogram of the compound N-1 of the present invention; Figure 3 is the HPLC chromatogram of the compound N-3 of the present invention; Figure 4 is the HPLC chromatogram of the compound N-60 of the present invention; Figure 1 Each reference numeral in represents: 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 Embodiments

[0019] 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. Instead, it is intended to cover alternatives, modifications, and equivalents that may be included within the scope defined by the appended claims.

[0020] In the terms "substituted" or "unsubstituted" used herein, "substituted" means that at least one hydrogen of a group is re-coordinated with substituents such as deuterium, aryl, heteroaryl, etc. "Aryl" herein refers to a group containing one or more aromatic rings, including but not limited to benzene, naphthalene, phenanthrene, fluorene, acenaphthene, etc. "Heteroaryl" herein refers to a heteroaryl group obtained by substituting one or more C in the structure of "aryl" with one or more heteroatoms. Terms such as "C6-C30", "C5-C30", "C1-C4", "C6-C20", "C5-C20" in the text respectively indicate that the groups they modify contain 6-30, 5-30, 1-4, 6-20, 5-20 carbon atoms. "Deuterium" in the present invention refers to a stable isotope of hydrogen, also known as heavy hydrogen, and its element symbol is D.

[0021] For those not specified with specific conditions in the examples, they are carried out according to conventional conditions or the conditions recommended by the manufacturer. For reagents or instruments not specified with the manufacturer, they are all conventional products that can be obtained by commercial purchase.

[0022] Example 1:

[0023] The synthesis method of compound N-1 is as follows:

[0024]

[0025] Step 1: Under an air atmosphere, add 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) to the reaction flask. After the addition is complete, heat the reaction solution to 120 °C and react for 24 h. Add 150 ml of toluene to the reaction solution, separate the layers, concentrate the organic phase to dryness, and obtain about 21.5 g of intermediate 1 by column chromatography with a yield of 85%; Step 2: Under nitrogen protection, add deuterated carbazole (14.87 g, 0.085 mol, 1 eq) and intermediate 1 (21.5, 0.085 mol, 1 eq) to the reaction flask, add 200 ml of DMF and cesium carbonate (69 g, 0.2125 mol, 2.5 eq). After the addition is complete, heat the reaction solution to reflux and react for 12 h. Take a sample and detect by HPLC until the reaction is complete. After cooling, add 200 ml of water for washing, filter by suction, and purify the filter cake by column chromatography using a petroleum ether / dichloromethane system to obtain about 27.74 g of intermediate 2 with a yield of 80%; Step 3: Under nitrogen protection, add intermediate 2 (27.84 g, 0.068 mol, 1 eq) into the reaction flask, add 300 ml of ultra-dry tetrahydrofuran, cool down to -78 °C, dropwise add 2.5 M n-butyllithium (28.56 ml, 0.0714 mol, 1.05 eq). After the dropping is completed, keep the reaction at the same temperature for 1 h, then dropwise add triisopropyl borate (15.34 g, 0.0816 mol, 1.2 eq). After the addition is completed, let it warm up to room temperature naturally, add saturated ammonium chloride aqueous solution, separate the layers, concentrate the organic phase to dryness, and recrystallize with ethyl acetate to obtain approximately 20.34 g of intermediate 3, with a yield of 80%; Step 4: Under nitrogen protection, add intermediate 3 (20.34 g, 0.0544 mol, 1 eq) and the triazine compound (14.5 g, 0.0544 mol, 1 eq) into the reaction flask, add 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). After the addition is completed, heat the reaction solution to reflux overnight. Take a sample for HPLC detection. After the reaction is completed, cool down the reaction solution, wash it with water, separate the layers, filter the organic phase through silica gel, concentrate it to dryness, and perform column chromatography to obtain approximately 19.87 g of compound N-1, with a yield of 65%.

[0026] Other compounds are prepared by a similar preparation method, 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, Table 1-23 as follows: Table 1-1

[0027] Table 1-2

[0028] Table 1-3

[0029] Table 1-4

[0030] Table 1-5

[0031] Table 1-6

[0032] Table 1-7

[0033] Table 1-8

[0034] Table 1-9

[0035] Table 1-10

[0036] Table 1-11

[0037] Table 1-12

[0038] Table 1-13

[0039] Table 1-14

[0040] Table 1-15

[0041] Table 1-16

[0042] Table 1-17

[0043] Table 1-18

[0044] Table 1-19

[0045] Table 1-20

[0046] Table 1-21

[0047] Table 1-22

[0048] Table 1-23

[0049] 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, Table 1-23 are shown in Table 2 below: Table 2 Compound FD - Mass Compound FD - Mass 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) Device performance test: Application Example 1: ITO was used as the anode substrate material of the reflective layer, and it was surface-treated with water, acetone, and N 2 plasma in sequence; above the ITO anode substrate, 10 nm of HT-1 doped with 5% NDP-9 was deposited to form a hole injection layer (HIL); 100 nm of HT-1 was evaporated above the hole injection layer (HIL) to form a first hole transport layer (HTL); GP-1 was vacuum-evaporated above the first hole transport layer (HTL) to form a second hole transport layer (GPL) with a thickness of 10 nm; the compound N-1 (N-type) and the compound P-19 (P-type) prepared in Example 1 of the present invention were co-evaporated as the light-emitting host material in a ratio of 5:5, and GD-1 was evaporated as the doping material (the amount of GD-1 was 8% of the total weight of the compounds N-1 and P-19) on the second hole transport layer (GPL) to form a light-emitting layer with a thickness of 20 nm; HB-1 was evaporated onto the light-emitting layer to obtain a hole blocking layer (HBL) with a thickness of 20 nm; 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; magnesium (Mg) and silver (Ag) were mixed in a ratio of 9:1 and evaporated above the electron transport layer (ETL) to form an electron injection layer (EIL) with a thickness of 50 nm; thereafter, silver (Ag) was evaporated above the electron injection layer to form a cathode with a thickness of 100 nm. On the above cathode sealing layer, 50 nm of DNTPD was deposited. In addition, the cathode surface was sealed with a UV-curing adhesive and a seal cap containing a dehumidifying agent to protect the organic electroluminescent device from being affected by oxygen or moisture in the atmosphere. Thus, an organic electroluminescent device was prepared.

[0050] The structural formulas of the compounds used in each application example are as follows:

[0051] Application Example 2 - 82: Replace compound N - 1 in the application example with 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 - 119, 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 - 329, 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, N - 422 respectively, and vapor - deposit it with P - type compound P - 19 or P - 40 as the light - emitting host material of the green light device. Under the condition that other conditions are the same as those in Application Example 1, the organic electroluminescent device of Application Example 2 - 82 is fabricated accordingly.

[0052] Comparative Example 1 - 5:

[0053] Replace compound N - 1 in the application example with comparative compounds D - 1, D - 2, D - 3, D - 4, D - 5 respectively, and vapor - deposit it with compound P - 19 or P - 40 as the light - emitting host material of the green light device. Under the condition that other conditions are the same as those in Application Example 1, the organic electroluminescent device of Comparative Example 1 - 5 is fabricated accordingly.

[0054] At a current density of 10 mA / cm 2Under the following conditions, the characteristics of the organic electroluminescent devices manufactured in the application examples were tested and compared with those of the organic electroluminescent devices manufactured in the control examples. The test results are shown in Tables 3-1, 3-2, 3-3, 3-4, and 3-5 below: Table 3-1

[0055] Table 3-2

[0056] Table 3-3

[0057] Table 3-4

[0058] Table 3-5

[0059] As can be seen from Tables 3-1, 3-2, 3-3, 3-4, and 3-5, at the same current density, when the N-type compound provided by the present invention is applied to an organic electroluminescent device and paired with a P-type compound with deuteration in the core region, compared with existing compounds, the luminous efficiency of the device is significantly improved, the turn-on voltage of the device decreases to varying degrees, and the power consumption of the device is relatively reduced.

[0060] The organic electroluminescent devices prepared in Control Examples 1-5 and some Application Examples were subjected to a luminous lifetime test. Under the test condition of a current density of 10 mA / cm 2 , the luminous lifetime T97% data (the time when the luminous brightness decreases to 97% of the initial brightness) was obtained. The test results are shown in Table 4 (with the lifetime data of Control Example 1 as a reference): Table 4

[0061] As can be seen from the above table, when 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 parameter conditions such as the current density, the service life of the device in the application examples of the present invention is significantly improved compared with the comparative examples.

[0062] Table 5. HPLC Chromatographic Data of Compounds N-1, N-3, and N-60 of the Present Invention

[0063] It should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention and not to limit them. Although the present invention has been described in detail with reference to the preferred embodiments, those of ordinary skill in the art should understand that the technical solutions of the present invention can be modified or equivalently replaced without departing from the spirit and scope of the technical solutions of the present invention, and they should all be covered by the scope of the claims of the present invention.

Claims

1. An organic electroluminescent compound, characterized in that: The structural formula is shown in the following formula (1): Formula (1) Where: R0-R7 each independently represents deuterium, deuterium-substituted or unsubstituted C6-C30 aryl, provided that at least seven of R0-R7 are deuterium; 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; L1 and L2 each independently represent a single bond; Ar1 and Ar2 are the same or different and represent a C6-C30 aryl group which may be substituted or unsubstituted with a substituent, provided that when R0-R 11 When neither of them is a deuterium-substituted or unsubstituted C6-C30 aryl group, at least one of Ar1 and Ar2 is a substituent-substituted or unsubstituted biphenyl group; The substituents of Ar1 and Ar2 are independently selected from one or more of 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 of them.

2. The organic electroluminescent compound according to claim 1, characterized in that: Ar1 and Ar2 are the same or different and represent phenyl or biphenyl groups which are substituted or unsubstituted with substituents; the substituents of Ar1 and Ar2 are each independently selected from one or more of deuterium, methyl, phenyl, deuterated methyl, and deuterated phenyl.

3. The organic electroluminescent compound according to claim 1, characterized in that R8-R 11 Medium, R8 or R 10 is a deuterium-substituted or unsubstituted C6-C30 aryl group, and at least one of the remaining three R groups is deuterium.

4. The organic electroluminescent compound according to claim 1, characterized in that Seven R groups among R0-R7 are deuterium, and the other non-deuterium group is phenyl or deuterated phenyl.

5. The organic electroluminescent compound according to claim 1, characterized in that: Selected from the following compounds:

6. 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, wherein the organic layer contains the organic electroluminescent compound according to any one of claims 1 to 5.

7. The organic electroluminescent device according to claim 6, characterized in that: The organic layer comprises 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 any one of claims 1 to 5.

8. The organic electroluminescent device according to claim 7, characterized in that: The light-emitting layer contains a light-emitting main material, and the light-emitting main material is composed of a first compound and a second compound. The first compound is the organic electroluminescent compound described in any one of claims 1 to 5, 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 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 each independently represent deuterium, a C6-C20 aryl group which may be substituted or unsubstituted with deuterium; R 12 and R 13 is deuterium, m1 is an integer selected from 0-3, m2 is an integer selected from 0-4, and n is an integer selected from 0-4.

9. The organic electroluminescent device as claimed in claim 8, characterized in that: L3, L4, L5 and L6 are each independently a single bond, phenylene or deuterated phenylene; Ar5, Ar6, Ar3 and Ar4 are each independently a substituted or unsubstituted phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl or N-containing heteroaryl, and the substituents of Ar5, Ar6, Ar3 and Ar4 are selected from one or more of deuterium, phenyl and deuterated phenyl.

10. The organic electroluminescent device according to claim 8, characterized in that: The second compound is selected from any one of the following compounds:

Citation Information

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