Amino compound and organic light-emitting device

Abstract

The invention relates to an amino compound and an organic light-emitting device, which realize synergistic improvement of a plurality of excellent performances through elaborate design of a molecular structure. According to the invention, deuteration is selectively carried out on active sites of the structure, so that the material has good thermal stability, chemical stability and photoelectric stability, and meanwhile, cost waste caused by deuteration of unnecessary sites is avoided, so that the manufacturing cost of the material is greatly reduced. Meanwhile, the compound has good carrier mobility, an exciton recombination region is further widened, the service life of a device is prolonged, and the efficiency of the device is improved. And # imgabs0 #.

Description

Technical Field

[0001] The invention relates to the technical field of organic electroluminescence, and in particular to an amine compound and an organic light-emitting 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] The composition structure of an organic electroluminescent device includes a cathode, an anode, and an organic layer disposed therebetween. The organic layer structure of OLED devices currently used in the industry is usually a multilayer structure, for example, including a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and other film layers. For an OLED device including the above-mentioned film 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 holes and electrons meet, excitons are formed. When the excitons transfer energy to the doping material, light is emitted through the radiation transition of the doping material.

[0004] In existing OLED devices, since the second hole transport material is not deuterated at the active sites of the material molecules and the sites with high electron cloud density, its chemical stability, thermal stability and photoelectric stability are poor, which in turn affects the life of the device.

[0005] The compounds of the present invention are all deuterated at the active sites of their respective structures, and therefore have good thermal stability, chemical stability and photoelectric stability. At the same time, the compounds of the present invention have good carrier mobility, further broaden the exciton recombination area, and thus improve the life and efficiency of the device. Summary of the invention

[0006] The purpose of the present invention is to provide an amino compound and an organic electroluminescent device in view of the above technical problems.

[0007] The purpose of the present invention can be achieved by the following measures: A structure as shown in Formula 1:

[0008] Ar1 and Ar2 are independently selected from the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl, anthracenyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, phenanthrenyl, triphenylfuranyl, and the substituents of Ar1 and Ar2 are selected from one or more of deuterium, fluorine, cyano, methyl, deuterated methyl, ethyl, deuterated ethyl, tert-butyl, deuterated tert-butyl, C6-C20 aryl, C6-C20 deuterated aryl, C3-C20 heteroaryl, and C3-C20 deuterated heteroaryl; L1 and L2 are independently selected from the following groups which are direct bonds, substituted or unsubstituted: C6-C12 aryl groups, C3-C20 heteroaryl groups, and the substituents of L1 and L2 are selected from one or more of deuterium, fluorine, cyano, methyl, deuterated methyl, ethyl, deuterated ethyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pyridyl, and pyrimidyl groups; A1-A8 are independently selected from one or more of hydrogen, deuterium, cyano, deuterated or undeuterated C1-C6 alkyl, deuterated or undeuterated C3-C8 cycloalkyl.

[0009] Preferably, a structure as shown in Formula 2:

[0010] Ar1 is selected from the following substituted or unsubstituted groups: phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, and the substituent of Ar1 is selected from one or more of deuterium, fluorine, cyano, methyl, deuterated methyl, ethyl, deuterated ethyl, tert-butyl, deuterated tert-butyl, C6-C12 aryl, and C6-C12 deuterated aryl; L1 is selected from a direct bond, a substituted or unsubstituted C6-C12 aryl group, and the substituent of L1 is selected from one or more of deuterium, fluorine, cyano, methyl, deuterated methyl, ethyl, deuterated ethyl, tert-butyl, deuterated tert-butyl, phenyl, and deuterated phenyl; A1-A8 are independently selected from one or more of hydrogen, deuterium, cyano, methyl, deuterated methyl, ethyl, deuterated ethyl, tert-butyl, and deuterated tert-butyl; Preferably, Ar1 is selected from the following substituted or unsubstituted groups: phenyl, biphenyl, dibenzofuranyl, dibenzothienyl, fluorenyl, and the substituent of Ar1 is selected from one or more of deuterium, methyl, deuterated methyl, ethyl, deuterated ethyl, tert-butyl, deuterated tert-butyl, phenyl, and deuterated phenyl; L1 is selected from a direct bond, a substituted or unsubstituted C6-C12 aryl group, and the substituent of L1 is selected from one or more of deuterium, fluorine, cyano, methyl, and deuterated methyl; A1-A8 are independently selected from one or more of hydrogen, deuterium, cyano, methyl, deuterated methyl, tert-butyl, and deuterated tert-butyl.

[0011] Further preferably, Ar1 is selected from the following substituted or unsubstituted groups: phenyl, biphenyl, dibenzofuranyl, dibenzothienyl, fluorenyl, and the substituent of Ar1 is selected from one or more of deuterium, methyl, deuterated methyl, tert-butyl, deuterated tert-butyl; L1 is selected from a direct bond, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, and the substituent of L1 is selected from one or more of deuterium, fluorine, cyano, methyl, and deuterated methyl; A1-A8 are independently selected from one or more of hydrogen, deuterium, methyl, deuterated methyl, tert-butyl, and deuterated tert-butyl.

[0012] More preferably, Ar1 is selected from the following substituted or unsubstituted groups: phenyl, biphenyl, dibenzofuranyl, dibenzothienyl, fluorenyl, and the substituent of Ar1 is selected from one or more of deuterium, methyl, and deuterated methyl; L1 is selected from a direct bond, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, and the substituent of L1 is selected from one or more of deuterium, methyl, and deuterated methyl; A1-A8 are independently selected from one or more of hydrogen, deuterium, tert-butyl, and deuterated tert-butyl.

[0013] In a preferred embodiment, the compound of the present invention can be any one of the following structural formulas: .

[0014] The deuteration rate of the sites where the spirobifluorene groups in the compounds are deuterated is 10%-100%.

[0015] Furthermore, the deuteration rate of the sites where the spirobifluorene groups in the compound are deuterated is 20%-100%.

[0016] Furthermore, the deuteration rate of the sites where the spirobifluorene groups in the compound are deuterated is 30%-95%.

[0017] Furthermore, the deuteration rate of the sites where the spirobifluorene groups in the compound are deuterated is 40%-90%.

[0018] 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 organic electroluminescent compound mentioned above.

[0019] Furthermore, the organic layer comprises a hole injection layer, a 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; at least one of the hole injection layer, the hole transport layer, the second hole transport layer, the light-emitting layer, the hole blocking layer, the electron transport layer, and the electron injection layer contains the above-mentioned organic electroluminescent compound.

[0020] Furthermore, the second hole transport layer contains the above-mentioned organic electroluminescent compound.

[0021] The compound of the invention is applied to the organic electroluminescent device, and the organic electroluminescent device can be used in the field of manufacturing electronic display equipment or OLED lighting equipment.

[0022] Beneficial effects of the present invention: The present invention relates to a novel organic electroluminescent compound, which realizes the synergistic improvement of multiple excellent properties through the careful design of the molecular structure.

[0023] 1. Selective deuteration at the active sites of the structure ensures that the material has good thermal stability, chemical stability and photoelectric stability, while avoiding the cost waste caused by deuteration at unnecessary sites, thereby greatly reducing the manufacturing cost of the material.

[0024] 2. At the same time, the compounds of the present invention have good carrier mobility, further broadening the exciton recombination area, thereby improving the life and efficiency of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0025] Figure 1 A schematic diagram of the structure of an organic electroluminescent device provided by the present invention; The numbers in the figure represent: 1-anode, 2-hole injection layer, 3-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.

[0026] Figure 2 It is the HPLC chart of compound 1 of the present invention.

[0027] Figure 3 is the DSC spectrum of compound 1 prepared in Example 1 of the present invention, Figure 3 It can be seen that the melting point temperature Tm value of compound 1 is 208.82°C.

[0028] Figure 4 is the TGA spectrum of compound 1 of the present invention, Figure 4 It can be seen that the thermal weight loss temperature Td value of compound 1 is 415.41°C. DETAILED DESCRIPTION

[0029] The following further illustrates and describes embodiments of various aspects. It should be understood that the description herein is not intended to limit the claims to the specific aspects described. On the contrary, it is intended to cover substitutions, modifications and equivalents that may be included in the spirit and scope of the present disclosure defined by the appended claims.

[0030] 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 all hydrogens in the group are not re-coordinated with deuterium.

[0031] The "aromatic group", "aryl" or "aromatic group" herein refers to a group containing one or more aromatic rings, and the aromatic rings here include but are not limited to benzene, naphthalene, phenanthrene, fluorene, acenaphthene, etc. The C6-C25 in the C6-C25 aromatic group means that the group contains 6-25 carbon atoms. Aromatic groups can be divided into monocyclic aromatic groups and polycyclic aromatic groups. Specific aromatic groups in the present invention include but are not limited to phenyl, biphenyl, terphenyl, anthracenyl, naphthyl, phenanthryl, fluorenyl, 9,9-spirobifluorenyl, 9,9-dimethylfluorenyl or 9,9-diphenylfluorenyl, etc. Aromatic groups can be substituted and unsubstituted.

[0032] The "heteroaryl" herein refers to a heteroaryl group obtained by replacing one or more C in the structure of the "aryl" with one or more heteroatoms (such as N, O or S). The heteroaryl here includes but is not limited to pyridine, pyrimidine, pyrrole, furan, thiophene, carbazole, dibenzofuran, dibenzothiophene, etc.

[0033] "Cycloalkyl" herein refers to a monocyclic or fused ring ("fused" ring means that each ring in the system shares a pair of adjacent carbon atoms with other rings in the system) group that is all carbon, wherein one or more rings are saturated alicyclic rings, which generally have 3-20 carbon atoms, preferably 3-12 carbon atoms, and more preferably 3-10 carbon atoms. Cycloalkyl can be divided into monocyclic alkyls having only one ring and fused cyclic alkyls having multiple rings. Examples of monocyclic alkyls include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane. Cycloalkyl can be substituted and unsubstituted.

[0034] The "deuterated aryl group" herein refers to a group in which one or more hydrogen atoms in an aromatic group are substituted with deuterium.

[0035] The "deuterated phenyl group" herein refers to a group in which one or more hydrogen atoms in a phenyl group are replaced by deuterium.

[0036] The "deuteration rate" herein refers to the probability of hydrogen being replaced by deuterium at a site.

[0037] If the specific conditions are not specified in the examples, the experiments were carried out under conventional conditions or conditions recommended by the manufacturer. If the manufacturers of the reagents or instruments are not specified, they are all conventional products that can be purchased commercially.

[0038] Example 1

[0039] Compound 1 was prepared as follows: Step 1:

[0040] Under nitrogen protection, 1-a (53.4 g, 0.2 mol) was added to the reaction bottle, 200 ml of ultra-dry tetrahydrofuran was added, the temperature was lowered to -78 ° C, 2.5 M n-butyl lithium (80 ml, 0.2 mol) was added dropwise, and after the addition was completed, heavy water (4 g, 0.2 mol) was added dropwise. After the addition was completed, the reaction was stirred for 1 h, and 100 ml of saturated ammonium chloride aqueous solution was added. The liquids were separated and the organic phase was concentrated to dryness to obtain about 35 g of compound 1-b with a yield of 92%.

[0041] Under nitrogen protection, compound 1-b (35 g, 0.1842 mol) was added to the reaction bottle, 200 ml of ultra-dry tetrahydrofuran was added, the temperature was lowered to -78 ° C, 2.5 M n-butyl lithium (74 ml, 0.1842 mol) was added dropwise, and the reaction was stirred for 30 min after the addition was completed. Triisopropyl borate (34 g, 0.1842 mol) was added dropwise. After the addition was completed, the reaction was kept warm for 1 h, and 100 ml of saturated ammonium chloride aqueous solution was added. The liquids were separated and the organic phase was concentrated to dryness to obtain about 26.69 g of compound 1-c with a yield of 92%.

[0042] Step 2:

[0043] Under nitrogen protection, compound 1-c (26.69 g, 0.17 mol) and compound 1-d (47.94 g, 0.17 mol) were added to a reaction flask, and 340 ml of toluene, 170 ml of ethanol, potassium carbonate (46.92 g, 0.34 mol) and 170 ml of ultrapure water were added. Nitrogen protection was continued for 5 minutes, and then tetrakistriphenylphosphine palladium (1.96 g, 0.0017 mol) was added. After the addition was completed, the temperature was raised and refluxed for reaction for 6 hours. After the reaction was completed, the temperature was lowered, 100 ml of water was added, the liquids were separated, the organic phase was concentrated to dryness, and then purified by column chromatography to obtain about 38.71 g of compound 1-e with a yield of 85%.

[0044] Step 3:

[0045] Under nitrogen protection, compound 1-e (38.71 g, 0.1445 mol) was dissolved in 200 ml of tetrahydrofuran, cooled to -78 ° C, and 2.5 M n-butyl lithium (57.8 ml, 0.1445 mol) was added dropwise. The reaction was completed for 30 minutes. A 200 ml tetrahydrofuran solution of compound 1-f (42.19 g, 0.1445 mol) was added dropwise at -78 ° C. The reaction was completed at room temperature for 2 hours. 300 ml of saturated ammonium chloride aqueous solution was added, stirred and separated, the organic phase was concentrated to dryness, dissolved in dichloromethane, and methylsulfonic acid (55.5 g, 0.578 mol) was added dropwise. The reaction was stirred for 2 hours. The reaction solution was concentrated to dryness, and 40 g of compound 1-g was obtained by column chromatography with a yield of 60%.

[0046] Step 4:

[0047] Under nitrogen protection, compound 1-g (40 g, 0.0862 mol) and 1-h (34.6 g, 0.0862 mol) were added to a reaction flask, and 500 ml of toluene was added, followed by sodium tert-butoxide (9.94 g, 0.1034 mol), palladium acetate (0.19 g, 0.862 mmol) and XPhos (0.82 g, 1.724 mmol). After the addition was completed, the temperature was raised to 100°C and stirred for 2 hours. The reaction was stopped, the temperature was lowered, the mixture was washed with water, the liquid was separated, the organic phase was concentrated, and then purified by column chromatography to obtain 47.87 g of compound 1 with a yield of 67%.

[0048] Compounds 2, 4, 5, 9, 10, 12, 14, 15, 22, 23, 28, 36, 37, 38, 40, 45, 46, 48, 49, 57, 64, 66, 67, 74, 75, 80, 88, 89, 92, 97, 100, 101, 114, 122, 125, 128, 137, 150, 164, 172, 176 were obtained in a similar manner. See Table 1-1, Table 1-2, Table 1-3, Table 1-4, Table 1-5, Table 1-6 for details: Table 1-1

[0049] Table 1-2

[0050] Table 1-3

[0051] Table 1-4

[0052] Table 1-5

[0053] Table 1-6

[0054] The synthesis and identification results of the compounds prepared in Table 1-1, Table 1-2, Table 1-3, Table 1-4, Table 1-5, and Table 1-6 above are shown in Table 2 below: Table 2 Compound FD-Quality Compound FD-Quality 1 m / z=829.31(C63H55D2N=829.46) 64 m / z=691.21(C52H33D2NO=691.28) 2 m / z=789.27(C60H51D2N=789.43) 66 m / z=805.97(C61H50D5N=806.46) 4 m / z=789.25(C60H51D2N=789.43) 67 m / z=805.98(C61H50D5N=806.46) 5 m / z=773.34(C59H47D2N=773.40) 74 m / z=693.95(C53H34D5N=694.34) 9 m / z=717.19(C55H39D2N=717.34) 75 m / z=693.96(C53H34D5N=694.34) 10 m / z=677.24(C52H35D2N=677.31) 80 m / z=805.97(C61H50D5N=806.46) 12 m / z=677.26(C52H35D2N=677.31) 88 m / z=693.95(C53H34D5N=694.34) 14 m / z=803.34(C61H53D2N=803.45) 89 m / z=805.98(C61H50D5N=806.46) 15 m / z=803.35(C61H53D2N=803.45) 92 m / z=805.95(C61H50D5N=806.46) 22 m / z=691.25(C53H37D2N=691.32) 97 m / z=693.94(C53H34D5N=694.34) 23 m / z=691.26(C53H37D2N=691.32) 100 m / z=693.95(C53H34D5N=694.34) 28 m / z=803.23(C61H53D2N=803.45) 101 m / z=805.98(C61H50D5N=806.46) 36 m / z=691.27(C53H37D2N=691.32) 114 m / z=805.97(C61H50D5N=806.46) 37 m / z=803.29 (C61H53D2N=803.45) 122 m / z=803.21(C61H53D2N=803.45) 38 m / z=803.31(C61H53D2N=803.45) 125 m / z=829.32(C63H55D2N=829.46) 40 m / z=803.31(C61H53D2N=803.45) 128 m / z=789.26(C60H51D2N=789.43) 45 m / z=691.29 (C53H37D2N=691.32) 137 m / z=829.22(C63H55D2N=829.46) 46 m / z=691.30(C53H37D2N=691.32) 150 m / z=789.28(C60H51D2N=789.43) 48 m / z=691.29(C53H37D2N=691.32) 164 m / z=829.22(C63H55D2N=829.46) 49 m / z=803.28(C61H53D2N=803.45) 172 m / z=717.18(C55H39D2N=717.34) 57 m / z=691.25(C53H37D2N=691.32) 176 m / z=803.22(C60H49D2NO=803.41) The above materials were subjected to basic performance tests, including thermal weight loss temperature Td and melting point temperature Tm. The test results are shown in Table 3 below.

[0055] Note: Thermal weight loss temperature Td is the temperature at which weight loss is 5% in a nitrogen atmosphere, and is measured on a TGA N-1000 thermogravimetric analyzer with a nitrogen flow rate of 10 mL / min. Tm (melting point) is measured by differential scanning calorimetry (DSC, Xinke DSCN-650) with a heating rate of 10°C / min.

[0056] Table 3 Test material (compound) Tm / ℃ Td / ℃ Test material (compound) Tm / ℃ Td / ℃ 1 208.82 415.41 64 204.34 408.28 2 178.32 410.32 66 197.26 398.87 4 195.67 391.24 67 187.94 392.47 5 201.52 397.41 74 199.41 403.65 9 198.12 404.12 75 203.92 421.32 10 190.95 413.52 80 216.37 425.13 12 207.61 405.14 88 205.98 397.31 14 196.47 406.30 89 213.36 407.94 15 211.71 422.36 92 192.37 408.57 22 186.13 426.19 97 186.74 401.30 23 195.26 413.94 100 219.15 418.61 28 204.35 408.61 101 204.67 391.53 36 196.69 417.50 114 196.34 397.21 37 206.54 406.75 122 193.49 394.67 38 214.97 418.65 125 203.11 413.91 40 188.31 395.42 128 197.46 404.60 45 197.49 409.36 137 198.10 401.57 46 209.34 413.87 150 187.36 399.20 48 189.32 396.21 164 191.95 394.81 49 196.84 406.18 172 186.12 403.46 57 206.15 418.64 176 217.66 414.57 According to the above data, the compounds synthesized in the present invention have excellent thermal stability, which means that the compounds conforming to the general structural formula of the present invention have excellent thermal stability and can meet the requirements for the use of organic electroluminescent materials.

[0057] Device performance test: Application Example 1: ITO was used as the reflective layer anode substrate material, and its surface was treated with water, acetone, and N2 plasma in sequence; 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); A hole transport layer (HTL) was formed by evaporating 100 nm of HT-1 on the hole injection layer (HIL); Vacuum evaporating the compound 1 of the present invention on the hole transport layer (HTL) to form a second hole transport layer (GPL) with a thickness of 10 nm; GH-2 and GH-1 were co-evaporated at a ratio of 5:5 (mass ratio) as the main luminescent materials, and GD-1 was evaporated as the doping material (the amount of GD-1 was 8% of the total weight of GH-1 and GH-2) on the second hole transport layer (GPL) to form a luminescent 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) at 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 onto the electron transport layer (ETL) to form an electron injection layer (EIL) with a thickness of 50 nm. Thereafter, silver (Ag) is evaporated onto the electron injection layer to form a cathode with a thickness of 100 nm, and a DNTPD with a thickness of 50 nm is deposited on the cathode sealing layer. In addition, the cathode surface is sealed with a UV curable adhesive and a sealing film (seal cap) containing a dehumidifier to protect the organic electroluminescent device from being affected by oxygen or moisture in the atmosphere. Thus, an organic electroluminescent device is prepared.

[0058]

[0059] Application Example 2-42 The compounds 2, 4, 5, 9, 10, 12, 14, 15, 22, 23, 28, 36, 37, 38, 40, 45, 46, 48, 49, 57, 64, 66, 67, 74, 75, 80, 88, 89, 92, 97, 100, 101, 114, 122, 125, 128, 137, 150, 164, 172, 176 in Examples 2-42 of the present invention are respectively used as the second hole transport material, and the other parts are consistent with those in Application Example 1, and the organic electroluminescent devices of Application Examples 2-42 are manufactured accordingly.

[0060] Comparative Examples 1-8: The difference from Application Example 1 is that compound D1 in patent CN104114672 A, compound D2 in patent CN112010760A, compounds D3, D4, D5, D6 in patent CN116323559A, and compounds D7 and D8 in patent CN119306618A are used as the second hole transport material, and the rest is the same as Application Example 1.

[0061] The characteristics of the organic electroluminescent device manufactured in the above application example and the organic electroluminescent device manufactured in the control example are that at a current density of 10 mA / cm 2 The results were shown in Table 4 below.

[0062] Table 4 Experimental Group Second hole transport layer <![CDATA[Current density (mA / cm 2 ).]]> Voltage (V) Luminous efficiency Emitting color Comparative Example 1 D1 10 3.70 157.6 Green Light Comparative Example 2 D2 10 3.76 161.4 Green Light Comparative Example 3 D3 10 3.65 168.5 Green Light Comparative Example 4 D4 10 3.69 170.1 Green Light Comparative Example 5 D5 10 3.71 172.5 Green Light Comparative Example 6 D6 10 3.67 167.2 Green Light Comparative Example 7 D7 10 3.47 187.9 green Comparative Example 8 D8 10 3.48 186.5 Green Light Application Example 1 1 10 3.22 219.3 Green Light Application Example 2 2 10 3.34 192.5 Green Light Application Example 3 4 10 3.41 194.3 Green Light Application Example 4 5 10 3.23 205.7 Green Light Application Example 5 9 10 3.24 209.4 Green Light Application Example 6 10 10 3.41 201.5 Green Light Application Example 7 12 10 3.32 195.9 Green Light Application Example 8 14 10 3.42 193.5 Green Light Application Example 9 15 10 3.35 189.0 Green Light Application Example 10 22 10 3.43 200.6 Green Light Application Example 11 23 10 3.28 186.2 Green Light Application Example 12 28 10 3.38 196.4 Green Light Application Example 13 36 10 3.40 207.3 Green Light Application Example 14 37 10 3.28 191.2 Green Light Application Example 15 38 10 3.33 194.4 Green Light Application Example 16 40 10 3.31 198.7 Green Light Application Example 17 45 10 3.33 196.0 Green Light Application Example 18 46 10 3.41 201.7 Green Light Application Example 19 48 10 3.30 189.3 Green Light Application Example 20 49 10 3.42 194.1 Green Light Application Example 21 57 10 3.43 194.6 Green Light Application Example 22 64 10 3.23 202.4 Green Light Application Example 23 66 10 3.40 196.7 Green Light Application Example 24 67 10 3.33 198.2 Green Light Application Example 25 74 10 3.44 199.1 Green Light Application Example 26 75 10 3.43 204.7 Green Light Application Example 27 80 10 3.46 203.5 Green Light Application Example 28 88 10 3.36 197.3 Green Light Application Example 29 89 10 3.44 194.3 Green Light Application Example 30 92 10 3.41 200.6 Green Light Application Example 31 97 10 3.43 193.2 Green Light Application Example 32 100 10 3.34 186.1 Green Light Application Example 33 101 10 3.36 189.6 Green Light Application Example 34 114 10 3.24 208.3 Green Light Application Example 35 122 10 3.44 191.1 Green Light Application Example 36 125 10 3.25 207.6 Green Light Application Example 37 128 10 3.46 204.3 Green Light Application Example 38 137 10 3.25 207.5 Green Light Application Example 39 150 10 3.37 191.4 Green Light Application Example 40 164 10 3.24 208.5 Green Light Application Example 41 172 10 3.22 214.8 Green Light Application Example 42 176 10 3.23 210.6 Green Light As can be seen from the above table, when the material of the present invention is applied to an organic electroluminescent device, at the same current density, the luminous efficiency is greatly improved, the starting voltage of the device is reduced, and the power consumption of the device is relatively reduced.

[0063] The organic electroluminescent devices prepared in the control examples 1-8 and the application examples 1-20 were respectively subjected to luminescence lifetime tests to obtain the luminescence lifetime T97% data (the time when the luminescence brightness decreases to 97% of the initial brightness). The test equipment was a TEO luminescent device lifetime test system. The results are shown in Table 5: Table 5 Experimental Group Hole Transport Materials (HTL) <![CDATA[Current density (mA / cm 2 ).]]> T97% Comparative Example 1 D1 10 95% Comparative Example 2 D2 10 96% Comparative Example 3 D3 10 100% Comparative Example 4 D4 10 105% Comparative Example 5 D5 10 108% Comparative Example 6 D6 10 102% Comparative Example 7 D7 10 115% Comparative Example 8 D8 10 113% Application Example 1 1 10 148% Application Example 2 2 10 128% Application Example 3 4 10 131% Application Example 4 5 10 144% Application Example 5 9 10 142% Application Example 6 10 10 136% Application Example 7 12 10 131% Application Example 8 14 10 138% Application Example 9 15 10 132% Application Example 10 22 10 125% Application Example 11 23 10 132% Application Example 12 28 10 121% Application Example 13 36 10 133% Application Example 14 37 10 122% Application Example 15 38 10 134% Application Example 16 40 10 133% Application Example 17 45 10 137% Application Example 18 46 10 126% Application Example 19 48 10 127% Application Example 20 49 10 135% It can be seen from the above table that when the material of the present invention is applied to an organic electroluminescent device, the service life is greatly improved at the same current density, and the material has broad application prospects.

[0064] It should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention rather than to limit it. 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. A compound, characterized in that Selected from the structure shown in Formula 1: ； In formula 1, Ar1 and Ar2 are independently selected from the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl, anthracenyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, phenanthrenyl, triphenylfuranyl, and the substituents of Ar1 and Ar2 are selected from one or more of deuterium, fluorine, cyano, methyl, deuterated methyl, ethyl, deuterated ethyl, tert-butyl, deuterated tert-butyl, C6-C25 aryl, C6-C25 deuterated aryl, C3-C20 heteroaryl, and C3-C20 deuterated heteroaryl; L1 and L2 are independently selected from the following groups which are direct bonds, substituted or unsubstituted: C6-C12 aryl groups, C3-C20 heteroaryl groups, and the substituents of L1 and L2 are selected from one or more of deuterium, fluorine, cyano, methyl, deuterated methyl, ethyl, deuterated ethyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pyridyl, and pyrimidyl groups; A1-A8 are independently selected from one or more of hydrogen, deuterium, cyano, deuterated or undeuterated C1-C6 alkyl, deuterated or undeuterated C3-C8 cycloalkyl.

2. A compound according to claim 1, characterized in that Selected from the structure shown in Formula 2: ； In formula 2, Ar1 is selected from the following substituted or unsubstituted groups: phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, and the substituent of Ar1 is selected from one or more of deuterium, fluorine, cyano, methyl, deuterated methyl, ethyl, deuterated ethyl, tert-butyl, deuterated tert-butyl, C6-C12 aryl, and C6-C12 deuterated aryl; L1 is selected from a direct bond, a substituted or unsubstituted C6-C12 aryl group, and the substituent of L1 is selected from one or more of deuterium, fluorine, cyano, methyl, deuterated methyl, ethyl, deuterated ethyl, tert-butyl, deuterated tert-butyl, phenyl, and deuterated phenyl; A1-A8 are independently selected from one or more of hydrogen, deuterium, cyano, methyl, deuterated methyl, ethyl, deuterated ethyl, tert-butyl, and deuterated tert-butyl.

3. A compound according to claim 1, characterized in that Ar1 is selected from the following substituted or unsubstituted groups: phenyl, biphenyl, dibenzofuranyl, dibenzothienyl, fluorenyl, and the substituent of Ar1 is selected from one or more of deuterium, methyl, deuterated methyl, ethyl, deuterated ethyl, tert-butyl, deuterated tert-butyl, phenyl, and deuterated phenyl; L1 is selected from a direct bond, a substituted or unsubstituted C6-C12 aryl group, and the substituent of L1 is selected from one or more of deuterium, fluorine, cyano, methyl, and deuterated methyl; A1-A8 are independently selected from one or more of hydrogen, deuterium, cyano, methyl, deuterated methyl, tert-butyl, and deuterated tert-butyl.

4. A compound according to claim 1, characterized in that Ar1 is selected from the following substituted or unsubstituted groups: phenyl, biphenyl, dibenzofuranyl, dibenzothienyl, fluorenyl, and the substituent of Ar1 is selected from one or more of deuterium, methyl, deuterated methyl, tert-butyl, and deuterated tert-butyl; L1 is selected from a direct bond, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, and the substituent of L1 is selected from one or more of deuterium, fluorine, cyano, methyl, and deuterated methyl; A1-A8 are independently selected from one or more of hydrogen, deuterium, methyl, deuterated methyl, tert-butyl, and deuterated tert-butyl.

5. A compound according to claim 1, characterized in that Ar1 is selected from the following substituted or unsubstituted groups: phenyl, biphenyl, dibenzofuranyl, dibenzothienyl, fluorenyl, and the substituent of Ar1 is selected from one or more of deuterium, methyl, and deuterated methyl; L1 is selected from a direct bond, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, and the substituent of L1 is selected from one or more of deuterium, methyl, and deuterated methyl; A1-A8 are independently selected from one or more of hydrogen, deuterium, tert-butyl, and deuterated tert-butyl.

6. A compound according to claim 1, characterized in that The compound is one of the following structural formulas: 。 7. A composition comprising the compound of any one of claims 1 to 6.

8. An organic electroluminescent device comprising the compound according to claim 1, characterized in that: The 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 according to any one of claims 1 to 6 or the composition according to claim 7.

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

10. The organic electroluminescent device according to claim 9, characterized in that: The second hole transport layer contains the compound according to any one of claims 1 to 6 or the composition according to claim 7.

11. The organic electroluminescent device according to claim 8, characterized in that: The compound of the invention is applied to the organic electroluminescent device, and the organic electroluminescent device is applied to the field of manufacturing electronic display equipment or OLED lighting equipment.

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