Compound, Organic Electroluminescent Device and Display Device

Abstract

The present invention discloses a compound, an organic electroluminescent device, and a display device. The compound has the structure represented by formula (I). When used in an organic electroluminescent device or display device, the compound is contained in the organic layer of the device and is particularly suitable for preparing a hole transport layer. The present invention aims to improve the performance of organic electroluminescent compound materials through the rational introduction of deuterium, thereby increasing the luminous efficiency and service life of the light-emitting device and its application. Furthermore, through the rational design of the deuterated position, deuteration can achieve both improved material and device performance and economical efficiency. #imgabs0# (I).

Description

Technical Field

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

[0002] OLED, short for Organic Light-Emitting Diode, is a current-type organic light-emitting device. Its operating principle is that, under the influence of an electric field, holes generated at the anode and electrons generated at the cathode migrate, injecting them into the hole-transport layer and electron-transport layer, respectively, before migrating to the light-emitting layer. When the holes and electrons meet in the light-emitting layer, they generate energy excitons, which excite the molecules of the luminescent material and ultimately produce visible light. Deuterium (D) is a stable, non-radioactive isotope found in nature, with a greater atomic mass than hydrogen. Studies have shown that incorporating deuterium atoms into OLED materials can stabilize the molecular structure, improve the luminous efficiency and stability of OLED devices, and extend their lifespan. However, practical verification shows that the specific improvement in material and device performance depends on the method used, and the introduction of deuterated materials can significantly increase production costs. Therefore, the question of how to rationally introduce deuterium and other modifying groups to achieve more cost-effective material and device performance improvements, while maintaining a certain cost, is a worthy concern in the industry. Summary of the Invention

[0003] The present invention aims to solve the above problems and provides a compound, an organic electroluminescent device and a display device.

[0004] The purpose of the present invention is achieved through the following technical solutions:

[0005] A compound characterized by having a structure as shown in formula (I):

[0006] (I)

[0007] In the above formula:

[0008] Ar1 and Ar2 each independently represent a different group, one of which is dimethylfluorene, and the other is a substituted or unsubstituted C6-C30 aryl group or a C6-C30 heteroaryl group, the substituent of the C6-C30 aryl group is selected from one or more of an alkyl group, a deuterated alkyl group, a phenyl group, a phenyl group substituted by an alkyl group, and a phenyl group substituted by a deuterated alkyl group; the substituent of the C6-C30 heteroaryl group is selected from a deuterated or undeuterated C6-C20 aryl group; (D)m represents m deuterium substituents attached to the phenyl ring, where m represents an integer from 1 to 5; (D)n represents n deuterium substituents attached to the phenyl ring, where n represents an integer from 1 to 4.

[0009] As a preferred embodiment, one of Ar1 and Ar2 is dimethylfluorene, and the other is selected from a biphenyl group, a terphenyl group, a biphenyl group substituted with a methyl group or a phenyl group, and a biphenyl group substituted with a deuterated methyl group.

[0010] As a preferred embodiment, one of Ar1 and Ar2 is dimethylfluorene, and the other is selected from substituted or unsubstituted dibenzofuranyl, and the substituent of the dibenzofuranyl is phenyl or deuterated phenyl.

[0011] As a preferred embodiment, m is 5 and n is 4.

[0012] As a preferred embodiment, one of Ar1 and Ar2 is selected from the group represented by any one of the structural formulas (1-1) to (1-5), and the other is selected from the group represented by any one of the structural formulas (2-1) to (2-4):

[0013]

[0014] Wherein, R1 and R2 are the same or different and represent phenyl, methyl or deuterated methyl; R3 and R4 are the same or different and represent phenyl or deuterated phenyl; i, j, p, q each independently represent an integer of 0 or 1; X represents O or S; * represents a connection site.

[0015] As a preferred embodiment, formula (I) is represented by structural formula (I-1) or (I-2):

[0016]

[0017] wherein R1 and R2 are the same or different and represent phenyl, methyl or deuterated methyl; R3 and R4 are the same or different and represent phenyl or deuterated phenyl; i, j, p and q are each independently an integer of 0 or 1; and X represents O or S.

[0018] As a preferred embodiment, the compound is selected from one of the following compounds:

[0019]

[0020]

[0021]

[0022]

[0023]

[0024]

[0025]

[0026]

[0027]

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038] An organic electroluminescent device, characterized in that it comprises a first electrode, a second electrode and an organic layer formed therebetween, wherein the organic layer contains the compound described in any of the above schemes.

[0039] Preferably, 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, wherein the first hole transport layer or the second hole transport layer contains the compound described in any one of the above items.

[0040] A display device, characterized by comprising the organic electroluminescent device as described in any one of the above items.

[0041] Beneficial effects of the present invention:

[0042] 1) The present invention improves the stability of organic electroluminescent compound materials by introducing deuterium, thereby improving the stability and service life of light-emitting devices using the materials;

[0043] 2) In the compounds of the present invention, since deuterium is introduced at the active sites of the compound structure, compared with fully deuterated or heavily deuterated compounds but not at the active sites, the deuteration of the compounds of the present invention improves material and device performance while being economical;

[0044] 3) While deuteration improves stability, the compounds of the present invention also effectively control their molecular weight, which is beneficial for controlling the evaporation and sublimation temperatures of the compounds, thereby improving the stability and yield of the production line;

[0045] 4) The compound of the present invention has good carrier mobility, which improves the luminous efficiency of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0046] Figure 1 A schematic structural diagram of an organic electroluminescent device provided by the present invention;

[0047] Figure 2 HPLC chart of compound 4 prepared in Example of the present invention;

[0048] Figure 3 The DSC spectrum of compound 4 prepared in Example of the present invention;

[0049] Figure 4 This is the TGA spectrum of compound 4 prepared in Example of the present invention.

[0050] 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

[0051] To further illustrate the technical solution of the present invention, the present invention is described in more detail below in conjunction with specific examples. Where specific conditions are not specified in the examples, conventional conditions or conditions recommended by the manufacturer were used. Where the manufacturer of the reagents or instruments is not specified, they are all conventional products that can be purchased commercially.

[0052] Example 1:

[0053]

[0054] Compound 4 was prepared as follows:

[0055] Step S1:

[0056] To a 1 L three-necked flask, add SM1 (50 g, 0.256 mol, 1 eq) and ultra-dry THF (250 ml). Cool to below -65°C, add 2.5 M n-butyl lithium (107.5 ml, 0.269 mol, 1.05 eq) dropwise, and stir at this temperature for 1 h. Then, add a solution of SM2 (27 g, 0.2432 mol, 0.95 eq) in ultra-dry THF (135 ml) dropwise, and stir at room temperature overnight.

[0057] The reaction was stopped and quenched by adding 400 ml of saturated aqueous ammonium chloride solution. The mixture was stirred and separated. The aqueous phase was extracted with DCM, and the organic phases were combined and dried over anhydrous sodium sulfate. The filtrate was concentrated to dryness under reduced pressure and used directly in the next reaction without purification.

[0058] Step S2:

[0059] Add ZJ1 (theoretical 55.35 g, 0.2432 mol, 1 eq), I2 (98.8 g, 0.289 mol, 1.6 eq), potassium carbonate (100.8 g, 0.7296 mol, 3 eq), and tert-butanol (500 ml) to a 1 L three-necked flask. Under N2 protection, heat to 90 °C and stir for 20–24 h.

[0060] The reaction was stopped and quenched by adding 500 ml of 50% aqueous sodium thiosulfate solution. The mixture was extracted three times with 300 ml of EA. The organic phases were combined and washed twice with water. The organic phase was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness under reduced pressure to obtain 53.88 g of a yellow oil with a two-step yield of 98.2%.

[0061] Step S3:

[0062] SM3 (58.61 g, 0.251 mol, 1 eq) and ultra-dry THF (300 ml) were added to a 1 L three-necked flask, cooled to below -65°C, and 2.5 M n-butyl lithium (106 ml, 0.264 mol, 1.05 eq) was added dropwise. After completion of the addition, the mixture was stirred at this temperature for 30 min. A solution of ZJ2 (53.88 g, 0.239 mol, 0.95 eq) in ultra-dry THF (200 ml) was added dropwise. After completion of the addition, the mixture was stirred at room temperature overnight.

[0063] The reaction was stopped and quenched by adding 400 ml of saturated aqueous ammonium chloride solution. The mixture was stirred and separated. The aqueous phase was extracted with DCM, and the organic phases were combined and dried over anhydrous sodium sulfate. The filtrate was concentrated to dryness under reduced pressure and used directly in the next reaction without purification.

[0064] Step S4:

[0065] ZJ3 (theoretical 90.8 g, 0.239 mol, 1 eq) and DCM (450 ml) were added to a 1 L single-necked flask, cooled to below 0°C, and methanesulfonic acid (91.9 g, 0.956 mol, 4 eq) was added. After the addition was complete, the mixture was moved to room temperature and stirred for 1-2 h. ZJ3 was monitored by HPLC to be ≤0.5%.

[0066] The reaction was stopped, 200 ml of ethanol was added, and most of the DCM was removed by concentration under reduced pressure at low temperature until there was almost no droplet. The filter cake was rinsed with ethanol 3 to 4 times, and the filter cake was air-dried at 85°C to obtain 60.5 g of a gray solid with a two-step yield of 70%.

[0067] Step S5:

[0068] To a 1 L three-necked flask, ZJ4 (40 g, 0.111 mol, 1 eq), SM4 (39.97 g, 0.111 mol, 1 eq), sodium tert-butoxide (12.8 g, 0.1332 mol, 1.2 eq), XPhos (2.12 g, 4.44 mmol, 0.04 eq), and toluene (400 ml) were added. Under nitrogen protection, palladium acetate (0.5 g, 2.22 mmol, 0.02 eq) was added. After the addition was complete, the temperature was raised to 100°C with stirring. ZJ4 concentration was monitored by HPLC to ≤ 0.5%.

[0069] Stop the reaction, filter through silica gel while hot, concentrate the filtrate to dryness under reduced pressure, add 100 ml of toluene and 400 ml of ethanol, stir and beat at 65 ° C for 2 h, cool and stir to crystallize overnight, filter, and recrystallize the filter cake three times with toluene / ethanol, filter, recrystallize the filter cake once with toluene, filter, and dry the filter cake at 85 ° C with air to obtain 45.13 g of off-white solid with HPLC purity of 99.9642% and a yield of 59.2%.

[0070] The following other compounds were obtained by a similar method, see 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 for details.

[0071] Table 1-1

[0072]

[0073] Table 1-2

[0074]

[0075] Table 1-3

[0076]

[0077] Table 1-4

[0078]

[0079] Table 1-5

[0080]

[0081] Table 1-6

[0082]

[0083] Table 1-7

[0084]

[0085] Table 1-8

[0086]

[0087] Table 1-9

[0088]

[0089] Table 1-10

[0090]

[0091] Table 1-11

[0092]

[0093] Table 1-12

[0094]

[0095] Table 1-13

[0096]

[0097] Table 1-14

[0098]

[0099] Table 1-15

[0100]

[0101] Table 1-16

[0102]

[0103] Table 1-17

[0104]

[0105] Table 1-18

[0106]

[0107] The synthesis and identification results of the compounds prepared by the above method are shown in Table 2 below.

[0108] Table 2

[0109] Compound FD-Quality Compound FD-Quality 1 m / z=686.34 (C52H30D9N=686.36) 3 m / z=700.35 (C53H32D9N= 700.37) 4 m / z=686.35 (C52H30D9N=686.36) 9 m / z=700.34 (C53H32D9N= 700.37) 12 m / z= 703.38 (C53H29D12N=703.39) 13 m / z=700.35 (C53H32D9N= 700.37) 16 m / z= 703.35 (C53H29D12N=703.39) 19 m / z=700.38 (C53H32D9N= 700.37) 21 m / z= 700.35 (C53H32D9N=700.37) 23 m / z=700.40 (C53H32D9N= 700.37) 24 m / z= 703.40 (C53H29D12N=703.39) 26 m / z=703.39 (C53H29D12N= 703.39) 34 m / z= 703.38 (C53H29D12N=703.39) 36 m / z=703.38 (C53H29D12N= 703.39) 38 m / z=714.37 (C54H34D9N=714.39) 43 m / z= 720.40 (C54H28D15N=720.42) 48 m / z=714.35 (C54H34D9N=714.39) 49 m / z= 714.40 (C54H34D9N=714.39) 51 m / z= 720.40 (C54H28D15N=720.42) 57 m / z=714.37 (C54H34D9N=714.39) 58 m / z=714.40 (C54H34D9N=714.39) 60 m / z=720.39 (C54H28D15N=720.42) 67 m / z=720.39 (C54H28D15N=720.42) 69 m / z=720.38 (C54H28D15N=720.42) 71 m / z=686.35 (C52H30D9N=686.36) 73 m / z=700.35 (C53H32D9N= 700.37) 74 m / z=686.34(C52H30D9N=686.36) 79 m / z=700.35 (C53H32D9N= 700.37) 82 m / z= 703.35 (C53H29D12N=703.39) 83 m / z=700.36 (C53H32D9N= 700.37) 86 m / z= 703.32 (C53H29D12N=703.39) 89 m / z=700.41 (C53H32D9N= 700.37) 91 m / z=700.39 (C53H32D9N= 700.37) 93 m / z=700.40 (C53H32D9N= 700.37) 94 m / z=703.41(C53H29D12N=703.39) 96 m / z=703.41(C53H29D12N=703.39) 104 m / z=703.40(C53H29D12N=703.39) 106 m / z=703.40(C53H29D12N=703.39) 108 m / z=714.41(C54H34D9N=714.39) 113 m / z=720.43(C54H28D15N=720.42) 118 m / z=714.38(C54H34D9N=714.39) 119 m / z=714.40(C54H34D9N=714.39) 121 m / z=720.39(C54H28D15N=720.42) 127 m / z=714.42(C54H34D9N=714.39) 128 m / z=714.38(C54H34D9N=714.39) 130 m / z=720.45(C54H28D15N=720.42) 137 m / z=720.38(C54H28D15N=720.42) 139 m / z=720.39(C54H28D15N=720.42) 141 m / z=686.37(C52H30D9N=686.36) 143 m / z=686.34(C52H30D9N=686.36) 147 m / z=700.35(C53H32D9N= 700.37) 148 m / z=703.31(C53H29D12N=703.39) 149 m / z=700.34(C53H32D9N= 700.37) 152 m / z=703.35(C53H29D12N=703.39) 153 m / z=700.32(C53H32D9N= 700.37) 156 m / z=703.35(C53H29D12N=703.39) 157 m / z=700.37(C53H32D9N= 700.37) 162 m / z=703.37(C53H29D12N=703.39) 164 m / z=703.38(C53H29D12N=703.39) 168 m / z= 700.14(C52H28D9ON=700.34 ) 169 m / z=776.31(C58H32D9ON=776.37 ) 172 m / z= 776.35(C58H32D9ON=776.37) 174 m / z=776.37(C58H32D9ON=776.37 ) 176 m / z=700.33(C52H28D9ON=700.34 ) 177 m / z= 700.33(C52H28D9ON=700.34 ) 178 m / z= 700.31(C52H28D9ON=700.34 ) 179 m / z=776.35(C58H32D9ON=776.37) 181 m / z= 775.34 (C58H32D9ON=776.37) 183 m / z=700.32 (C52H28D9ON=700.34) 185 m / z=700.32 (C52H28D9ON=700.34) 187 m / z=700.35 (C52H28D9ON=700.34) 188 m / z=776.35 (C58H32D9ON=776.37) 190 m / z=700.18 (C52H28D9ON=700.34) 193 m / z=700.25 (C52H28D9ON=700.34) 195 m / z=700.29 (C52H28D9ON=700.34)

[0110] Basic performance tests were conducted on the above materials, including thermal weight loss temperature Td and melting point temperature Tm. The test results are shown in Table 3 below.

[0111] Table 3

[0112] Test material (compound) Td / ℃ Tm / ℃ Test material (compound) Td / ℃ Tm / ℃ 1 417.66℃ 200.76℃ 3 409.12℃ 198.33 ℃ 4 419.59℃ 205.43℃ 9 410.97℃ 197.54℃ 12 412.30℃ 201.61℃ 13 410.64℃ 197.10℃ 16 413.14℃ 205.12℃ 19 413.21℃ 204.62℃ 21 412.60℃ 204.98℃ 23 411.59℃ 204.61℃ 24 414.79℃ 203.14℃ 26 413.60℃ 205.41℃ 34 413.55℃ 204.36℃ 36 412.98℃ 203.69℃ 38 389.84℃ 186.45℃ 43 392.69℃ 184.95℃ 49 390.10℃ 190.35℃ 49 389.41℃ 187.64℃ 51 393.61℃ 192.64℃ 57 390.43℃ 192.68℃ 58 391.20℃ 192.76℃ 60 394.01℃ 185.94℃ 67 393.32℃ 187.69℃ 69 392.64℃ 186.91℃ 71 416.64℃ 196.77℃ 73 410.95℃ 203.64℃ 74 417.69℃ 198.96℃ 79 411.31℃ 202.37℃ 82 412.75℃ 195.64℃ 83 413.10℃ 200.76℃ 86 414.20℃ 195.30℃ 89 412.12℃ 200.31℃ 91 409.32℃ 191.37℃ 93 413.25℃ 197.56℃ 94 415.02℃ 205.97℃ 96 414.92℃ 199.67℃ 104 416.20℃ 204.16℃ 106 414.98℃ 197.46℃ 108 403.13℃ 188.43℃ 113 406.84℃ 192.37℃ 118 404.50℃ 190.51℃ 119 402.17℃ 188.19℃ 121 407.21℃ 195.39℃ 127 404.64℃ 190.62℃ 128 403.55℃ 187.98℃ 130 407.30℃ 190.34℃ 137 408.21℃ 190.57℃ 139 406.85 ℃ 189.78℃ 141 417.61℃ 200.61℃ 143 416.14℃ 197.56℃ 147 409.26℃ 198.55℃ 148 411.31℃ 200.85℃ 149 408.85℃ 196.34℃ 152 409.14℃ 195.68℃ 153 408.10℃ 196.79℃ 156 410.87℃ 201.74℃ 157 407.66℃ 194.64℃ 162 410.20℃ 200.05℃ 164 411.10℃ 205.87℃ 168 425.64℃ 215.62℃ 169 430.14℃ 220.54℃ 172 431.42℃ 222.76℃ 174 424.34℃ 217.95℃ 176 425.32℃ 215.10℃ 177 426.21℃ 215.42℃ 178 424.75℃ 217.95℃ 179 430.10℃ 219.85℃ 181 430.91℃ 224.15℃ 183 425.31℃ 214.39℃ 185 425.21℃ 218.47℃ 187 426.32℃ 220.72℃ 188 432.32℃ 227.54℃ 190 424.10℃ 220.54℃ 193 426.69℃ 223.10℃ 195 425.33℃ 219.32℃

[0113] Note: Thermogravimetric loss temperature (Td) is the temperature at which the weight loss reaches 5% in a nitrogen atmosphere, and was measured on a TGA N-1000 thermogravimetric analyzer with a nitrogen flow rate of 10 mL / min. The melting point (Tm) was measured by differential scanning calorimetry (DSC, Xinke DSC N-650) at a heating rate of 10°C / min.

[0114] It can be seen from the above data that the compound synthesized in the present invention has excellent thermal stability and can meet the requirements for use as an organic electroluminescent material.

[0115] Device performance test:

[0116] Application Example 1:

[0117] The organic electroluminescent device is prepared by the following process:

[0118] ITO was used as the reflective layer anode substrate material, and its surface was treated with water, acetone, and N2 plasma in sequence;

[0119] 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);

[0120] A 100 nm layer of HT-1 was evaporated on the hole injection layer (HIL) to form the first hole transport layer (HTL);

[0121] Compound 4 of the present invention was vacuum evaporated on the first hole transport layer (HTL) to form a second hole transport layer (GPL) with a thickness of 10 nm;

[0122] GH-2 and GH-1 were co-evaporated at a ratio of 5:5 (mass ratio) as the luminescent host materials, and GD-1 was evaporated as the dopant 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 20nm thick luminescent layer;

[0123] HB-1 was evaporated onto the light-emitting layer to obtain a hole blocking layer (HBL) with a thickness of 20 nm;

[0124] 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.

[0125] Magnesium (Mg) and silver (Ag) in a 9:1 ratio were evaporated onto the electron transport layer (ETL) to form a 50nm thick electron injection layer (EIL). Silver (Ag) was then evaporated onto the EIL to form a 100nm thick cathode. DNTPD was then deposited on the cathode sealing layer to a thickness of 50nm.

[0126] In addition, the cathode surface is sealed with a UV curable adhesive and a seal cap containing a dehumidifier to protect the organic electroluminescent device from being affected by oxygen or moisture in the atmosphere. Thus, the organic electroluminescent device is prepared.

[0127] Other compounds used in the above process are as follows:

[0128]

[0129] Application Example 2-75: The other compounds synthesized 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, and Table 1-18 are used as the second hole transport layer material, and the other parts are consistent with the conditions in Application Example 1 to produce the organic electroluminescent device of Application Example 2-75.

[0130] Comparative Examples 1-6: Compounds P1-P6 were used as the second hole transport layer materials respectively, and other conditions were consistent with those of Application Example 1 to produce organic electroluminescent devices of Comparative Examples 1-6.

[0131] The structures of the compounds P1-P6 are as follows:

[0132]

[0133] The characteristics of the organic electroluminescent device manufactured in the above application example and the organic electroluminescent device manufactured in the comparative example are that the current density is 10mA / cm 2 The results are shown in Table 4 below.

[0134] Table 4

[0135] Test items Second hole transport layer compound Voltage (V) Luminous efficiency (Cd / A) Test items Second hole transport layer compound Voltage (V) Luminous efficiency (Cd / A) Comparative Example 1 P1 3.82 160.8 Application Example 36 96 3.16 215.6 Comparative Example 2 P2 3.51 189.8 Application Example 37 104 3.13 217.1 Comparative Example 3 P3 3.69 170.1 Application Example 38 106 3.16 215.3 Comparative Example 4 P4 3.49 194.9 Application Example 39 108 3.18 213.9 Comparative Example 5 P5 3.75 167.4 Application Example 40 113 3.09 219.8 Comparative Example 6 P6 3.60 178.2 Application Example 41 118 3.18 213.9 Application Example 1 1 3.48 204.0 Application Example 42 119 3.20 212.7 Application Example 2 3 3.44 208.1 Application Example 43 121 3.11 216.9 Application Example 3 4 3.45 207.3 Application Example 44 127 3.20 213.0 Application Example 4 9 3.44 207.9 Application Example 45 128 3.20 213.1 Application Example 5 12 3.15 215.5 Application Example 46 130 3.01 220.3 Application Example 6 13 3.40 208.9 Application Example 47 137 3.05 219.7 Application Example 7 16 3.16 215.8 Application Example 48 139 3.15 217.8 Application Example 8 19 3.39 209.2 Application Example 49 141 3.44 207.8 Application Example 9 21 3.37 210.3 Application Example 50 143 3.45 206.7 Application Example 10 23 3.45 207.9 Application Example 51 147 3.40 208.1 Application Example 11 24 3.16 215.4 Application Example 52 148 3.17 214.9 Application Example 12 26 3.20 213.0 Application Example 53 149 3.38 209.2 Application Example 13 34 3.12 216.3 Application Example 54 152 3.15 215.8 Application Example 14 36 3.46 205.7 Application Example 55 153 3.44 207.3 Application Example 15 38 3.17 214.0 Application Example 56 156 3.16 214.6 Application Example 16 43 3.07 219.8 Application Example 57 157 3.40 209.5 Application Example 17 48 3.21 212.9 Application Example 58 162 3.17 214.6 Application Example 18 49 3.21 212.7 Application Example 59 164 3.20 213.8 Application Example 19 51 3.14 216.8 Application Example 60 168 3.55 202.3 Application Example 20 57 3.20 213.7 Application Example 61 169 3.53 203.1 Application Example 21 58 3.22 211.9 Application Example 62 172 3.50 204.7 Application Example 22 60 3.05 219.8 Application Example 63 174 3.53 203.5 Application Example 23 67 3.14 217.8 Application Example 64 176 3.58 200.9 Application Example 24 69 3.02 220.1 Application Example 65 177 3.51 204.1 Application Example 25 71 3.45 205.3 Application Example 66 178 3.53 203.7 Application Example 26 73 3.40 208.6 Application Example 67 179 3.38 210.4 Application Example 27 74 3.43 204.9 Application Example 68 181 3.50 204.2 Application Example 28 79 3.45 206.8 Application Example 69 183 3.55 202.9 Application Example 29 82 3.21 212.4 Application Example 70 185 3.52 201.8 Application Example 30 83 3.45 207.6 Application Example 71 187 3.48 205.4 Application Example 31 86 3.16 215.8 Application Example 72 188 3.39 209.3 Application Example 32 89 3.45 207.3 Application Example 73 190 3.40 208.7 Application Example 33 91 3.41 208.4 Application Example 74 193 3.50 203.5 Application Example 34 93 3.38 210.0 Application Example 75 195 3.36 210.2 Application Example 35 94 3.15 215.7

[0136] The luminous colors of application examples 1-75 are all green, and the x value range in the CIE color coordinates is between 0.21 and 0.28, and the y value range is between 0.68 and 0.75.

[0137] As can be seen from the table above, when the compounds of the present invention are applied to organic electroluminescent devices, at the same current density:

[0138] 1) Compared to the control example using compound P1 (non-deuterated), the luminous efficiency of the device in the application example of the present invention was significantly improved, the device startup voltage was reduced, and the device power consumption was relatively reduced. Compared to the control examples using compounds P2, P3, and P5 (non-deuterated or insufficiently deuterated at the active site), the luminous efficiency of the device in the application example of the present invention was improved to varying degrees.

[0139] 2) Compared to the control example using compound P4 (deuterated at positions covering the active site and also deuterated at other positions), the luminous efficiency and power consumption of the device using the present invention are basically at the same level. However, due to the reduction in the amount of deuterated benzene, the production cost can be significantly reduced, making it more economical for industrial application.

[0140] 3) Compared with the control example using compound P6 (an amine group with a different structure), the luminous efficiency of the device in the application example of the present invention is improved, the starting voltage of the device is reduced, and the power consumption of the device is relatively reduced.

[0141] Next, the organic electroluminescent devices prepared in the control examples 1-6 and some application examples were tested for luminescence lifetime to obtain the luminescence lifetime T97% data (the time it takes for the luminescence brightness to decrease to 97% of the initial brightness). The test equipment was a TEO light-emitting device lifetime test system, and the test conditions were a current density of 10 mA / cm 2 The lifespan data of the P1 compound control example was used as a reference. The results are shown in Table 5:

[0142] Table 5

[0143] Test items Second hole transport layer compound T97% Test items Second hole transport layer compound T97% Comparative Example 1 P1 100% Application Example 28 79 135% Comparative Example 2 P2 120% Application Example 29 82 136% Comparative Example 3 P3 109% Application Example 30 83 134% Comparative Example 4 P4 128% Application Example 35 94 135% Comparative Example 5 P5 102% Application Example 39 108 131% Comparative Example 6 P6 119% Application Example 47 130 134% Application Example 1 1 141% Application Example 51 143 144% Application Example 4 4 143% Application Example 52 148 137% Application Example 5 12 138% Application Example 53 149 138% Application Example 6 13 135% Application Example 54 152 140% Application Example 7 16 138% Application Example 60 168 150% Application Example 15 38 130% Application Example 69 183 148% Application Example 16 43 133% Application Example 75 193 146% Application Example 27 74 143%

[0144] As can be seen from the above table, compared with the control examples, the compounds of the present invention are applied to organic electroluminescent devices, and at the same current density, the device service life is improved to varying degrees.

[0145] 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. A compound, characterized in that It has a structure as shown in formula (I): （I） In the above formula: Ar1 and Ar2 each independently represent a different group, one of Ar1 and Ar2 is selected from a group represented by any one of the structural formulas (1-1) to (1-3), and the other is selected from a group represented by any one of the structural formulas (2-1) to (2-4): ; in: R1 and R2 are the same or different and represent phenyl, methyl or deuterated methyl; i and j each independently represent an integer of 0 or 1; * indicates the attachment site; (D) m represents m deuterium substituents attached to the benzene ring, and m represents 5; (D)n represents n deuterium substituents attached to the benzene ring, and n represents 4.

2. The compound according to claim 1, wherein Formula (I) is represented by formula (I-1): ; in: R1 and R2 are the same or different and represent phenyl, methyl or deuterated methyl; i and j each independently represent an integer of 0 or 1.

3. The compound according to claim 1, wherein One of the following compounds: 。 4. An organic electroluminescent device, characterized in that: The invention comprises a first electrode, a second electrode and an organic layer formed therebetween, wherein the organic layer contains the compound according to any one of claims 1 to 3.

5. The organic electroluminescent device according to claim 4, wherein: 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, wherein the first hole transport layer or the second hole transport layer contains the compound according to any one of claims 1 to 3.

6. A display device, characterized in that: The organic electroluminescent device according to claim 4 or 5 is included.

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