OLED (Organic Light Emitting Diode) compound, application thereof and luminescent device

Abstract

The invention provides an OLED (Organic Light Emitting Diode) compound, application thereof and a luminescent device, and belongs to the technical field of organic photoelectric materials, the OLED compound has a structure as shown in a formula I, the driving voltage of the organic electroluminescent device can be reduced, the luminous efficiency of the device can be improved, and the service life of the device can be prolonged.

Description

Technical Field

[0001] This invention belongs to the field of organic optoelectronic materials technology, and relates to an OLED compound and its applications, as well as light-emitting devices. Background Technology

[0002] Organic electroluminescent devices, as a novel display technology, possess unique advantages such as self-illumination, wide viewing angle, low energy consumption, high efficiency, thinness, rich colors, fast response speed, wide applicable temperature range, low driving voltage, the ability to manufacture flexible, bendable, and transparent display panels, and environmental friendliness. They can be applied to flat panel displays and next-generation lighting.

[0003] Currently, organic electroluminescence has become the mainstream display technology, and correspondingly, various novel materials have been developed to prepare organic thin film layers. However, with the development of society and technology, people have placed higher demands on the various performance aspects of organic electroluminescent devices, especially in terms of luminous efficiency, lifetime, and voltage. Therefore, there is an urgent need in this field to develop more types and higher-performance organic thin film layer materials to meet people's higher requirements for organic electroluminescent devices. Summary of the Invention

[0004] To address the shortcomings of existing technologies, this invention provides an OLED compound and its applications, as well as a light-emitting device, which solves the technical problem that organic electroluminescent devices cannot meet higher requirements in terms of luminous efficiency, lifetime, and voltage performance.

[0005] To achieve the above objectives, the present invention provides the following technical solution:

[0006] In a first aspect, the present invention provides an OLED compound having a structure as shown in Formula I:

[0007]

[0008] Formula I,

[0009] Among them, R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl groups having 1-30 carbon atoms, and substituted or unsubstituted C3-C groups. 30 cycloalkyl, substituted or unsubstituted C1-C 30 Any one of alkoxy, trialkylsilyl, dialkylarylsilyl, alkylarylamino, substituted or unsubstituted aryl with 6-30 carbon atoms, or substituted or unsubstituted heteroaryl with 3-30 carbon atoms.

[0010] Preferably, any two adjacent substitution positions of R1, R2, R3, R4, R5, R6, R7, R8, and R9 independently form a cyclic group, wherein the cyclic group is selected from any one of naphthalene, anthracene, phenanthrene, benzo[a]phenanthrene, fluorene, furan, thiophene, carbazole, pyridine, and pyrimidine.

[0011] Preferably, the OLED compound satisfies at least one of the following conditions:

[0012] The heteroatom of the heteroaryl group is selected from any one of N, O, and S;

[0013] The halogen is F;

[0014] The alkyl group having 1-30 carbon atoms is methyl or tert-butyl;

[0015] The C3-C 30 The cycloalkyl group is cyclohexyl;

[0016] The C1-C 30 The alkoxy group is a methoxy group.

[0017] Preferably, R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each independently selected from the following non-simple groups:

[0018] .

[0019] Preferably, when at least one of R1, R2, R3, R4, R5, R6, R7, R8, and R9 is a non-simple group, the hydrogen on each of R1, R2, R3, R4, R5, R6, R7, R8, and R9 is independently converted by deuterium, halogen, or C1-C. 10 Alkyl, C3-C 10 cycloalkyl, C6-C 20 Aryl, C3-C 20 Any substitution of a heteroaryl group.

[0020] Preferably, R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each independently selected from any one or more combinations of benzene, naphthalene, phenanthrene, benzo[a]phenanthrene, biphenyl, furan, thiophene, fluorene, and xanthene.

[0021] Preferably, R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each independently selected from any of the following structures.

[0022]

[0023] .

[0024] Preferably, R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each independently selected from any one or more combinations of benzene, naphthalene, phenanthrene, benzo[a]phenanthrene, biphenyl, furan, thiophene, fluorene, and xanthene that are partially or completely substituted with deuterium.

[0025] Preferably, R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each independently selected from any of the following structures.

[0026] .

[0027] Preferably, the OLED compound is selected from any one of the following compounds P1 to P148:

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046] .

[0047] In a second aspect, the present invention provides an application of the OLED compound described in the first aspect in the preparation of luminescent materials.

[0048] Thirdly, the present invention provides a light-emitting device, the light-emitting device comprising the OLED compound described in the first aspect.

[0049] Compared with existing technologies, it has the following beneficial effects:

[0050] The OLED compounds of this invention can be used to prepare organic electroluminescent devices. By designing the structure of the OLED compounds, they have excellent transmission and luminescence properties. When used as luminescent layer materials, they can reduce the driving voltage of organic electroluminescent devices, improve the luminous efficiency of the devices, and extend the device lifespan. Attached Figure Description

[0051] To more clearly illustrate the technical solutions in the embodiments of the present invention or the prior art, the drawings used in the description of the embodiments or the prior art will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present invention. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0052] Figure 1 This is a schematic diagram of the structure of the organic electroluminescent device provided in the device embodiment.

[0053] Among them, 1-substrate, 2-anode layer, 3-hole injection layer, 4-first hole transport layer, 5-second hole transport layer, 6-light emission layer, 7-hole blocking layer, 8-electron transport layer, 9-electron injection layer, and 10-cathode layer. Detailed Implementation

[0054] To facilitate understanding of the present invention, the following embodiments are provided. Those skilled in the art should understand that these embodiments are merely illustrative and should not be construed as limiting the scope of the invention.

[0055] This application provides an OLED compound and its application, as well as a light-emitting device. The OLED compound has a structure as shown in Formula I, which can reduce the driving voltage of organic electroluminescent devices, improve the luminous efficiency of the devices, and extend the device lifespan.

[0056]

[0057] (I).

[0058] The technical solution in this application is to solve the above-mentioned technical problems. The general idea is to first synthesize the key intermediates M1 and / or M5, and then synthesize the target product P.

[0059] First, the general formulas for the synthesis of key intermediates M1 and M5 are as follows:

[0060] ,

[0061] Where X = I, Br, Cl, and R' is a substituted or unsubstituted aromatic group, the key intermediates M1 and M5 are listed in Table 1.

[0062] Table 1. Structure of some key intermediates M1 and M5

[0063]

[0064] Secondly, the synthesis of the target product P includes two routes: general formula 1 and general formula 2.

[0065] The general formula for synthesis is:

[0066]

[0067]

[0068]

[0069] Among them, Ar' is the same as or different from Ar”, and X and X' = Br and Cl.

[0070] The general formula for synthesis is as follows:

[0071] .

[0072] Example 1 of intermediate preparation

[0073] This example of intermediate preparation provides a method for synthesizing intermediate M1-1, and the specific synthesis steps are as follows:

[0074]

[0075] Add A1-1 (100g, 0.46mol) and ethanol (1000mL) to the reaction flask. Under nitrogen protection, stir and heat to 40-50℃. Add ammonia water (25%-28% concentration, 107g) to the flask. After stirring for 30min, add hydrazine hydrate (57.57g). Then react at 40-50℃ for 2 hours. After the solid has completely precipitated, concentrate the reaction system to dryness under reduced pressure. Then add A2-1 (56.17g, 0.46mol) and PPA (polyphosphoric acid, the same below) (800g). Under nitrogen protection, heat to 120-130℃ and stir for 5h. After the reaction was completed, the temperature was lowered to 20-30℃, and 1000mL of water was slowly added to the reaction system. The mixture was stirred vigorously until completely dissolved, and then stirred vigorously for 3 hours. The solid precipitated, was filtered, and the solid was crystallized with ethanol to obtain 113.43g of off-white solid M1-1, GC=99.75%, yield 85%.

[0076] Mass spectrometry analysis of intermediate M1-1 showed a mass-to-charge ratio (m / z) of m / z = 290.0. Nuclear magnetic resonance (NMR) analysis of intermediate M1-1 showed the following ¹H NMR (600 MHz, Chloroform-d) values: δ 8.29–8.24 (m, 2H), 8.12 (dd, J = 8.3, 1.6 Hz, 1H), 7.97 (dd, J = 8.1, 1.5 Hz, 1H), 7.75–7.69 (m, 1H), 7.58 (t, J = 7.8 Hz, 2H), 7.37 (t, J = 8.2 Hz, 1H).

[0077] Examples of intermediate preparation 2-14

[0078] Examples 2 to 14 of intermediate preparations each provide an intermediate, the synthesis method of which is the same as that of intermediate M1-1, the only difference being that the raw material A1-1 in intermediate preparation example 1 is replaced with the corresponding amount of other raw material A1 (see Table 2), and the raw material A2-1 is replaced with the corresponding amount of other raw material A2 (see Table 2). Other conditions are the same as those of intermediate M1-1. The intermediates are detected by mass spectrometry, and the test data are shown in Table 2. The yield of the intermediates is shown in Table 2.

[0079] Table 2. Mass spectrometry data and yields of raw materials and intermediates used in Examples 2-14 of intermediate preparation.

[0080]

[0081]

[0082] Example 15 of intermediate preparation

[0083] This example of intermediate preparation provides a method for synthesizing intermediate M5-1, and the specific synthesis steps are as follows:

[0084]

[0085] (1) Synthesis of intermediate M2-1

[0086] THF (1000 mL) and M1-1 (100 g, 0.34 mol) were added to a dry reaction flask. The mixture was cooled to -78 °C under nitrogen protection using liquid nitrogen. Then, 2.5 M n-BuLi (163.2 mL, 0.408 mol) was added dropwise. After the addition was complete, the reaction was continued at -78 °C for 1 h. Trimethyl borate (42.4 g, 0.408 mol) was then added to the flask, maintaining the temperature below -78 °C throughout the process. After the addition was complete, the reaction continued for 2 h before being brought to room temperature to terminate the reaction. The reaction solution was quenched with dilute hydrochloric acid, extracted with ethyl acetate, and the ethyl acetate phase was washed with water until neutral. The solution was then concentrated to obtain a crude product. The crude product was purified with dichloromethane and dried to obtain 79.77 g of M2-1, with a yield of 92.00%. Mass spectrometry analysis showed a mass-to-charge ratio of m / z = 255.18.

[0087] (2) Synthesis of intermediate M3-1

[0088] M2-1 (79.77 g, 0.31 mol), A3-1 (68.65 g, 0.31 mol, CAS: 84459-33-6), potassium carbonate (42.84 g, 0.62 mol), toluene (800 mL), ethanol (300 mL), and water (300 mL) were added to the reaction flask. Under nitrogen protection, the temperature was raised to 75 °C, and then PdCl2(pph3)2 (0.65 g) was rapidly added. The reaction was maintained at 75–80 °C for 12 h to terminate the reaction. After the reaction was complete, the temperature was lowered to room temperature. The reaction solution was extracted, washed with water, and concentrated to obtain a crude product. The crude product was crystallized from toluene and ethanol to obtain 103.22 g of M3-1, with a yield of 95.2%. Mass spectrometry analysis showed a mass-to-charge ratio of m / z = 350.11.

[0089] (3) Synthesis of intermediate M4-1

[0090] The M3-1 obtained above (103.22 g, 0.3 mol) was added to a reaction flask and dissolved in THF (1000 mL). Then, (methoxymethyl)triphenylphosphine chloride (114.28 g, 0.3 mol) was added. Under nitrogen protection, sodium tert-butoxide (57.66 g, 0.6 mol) was added to the flask, with the temperature controlled to not exceed 30°C during the addition process. After the addition was complete, the reaction was continued for 12 hours and then stopped. The reaction solution was quenched, extracted, washed with water, and concentrated to obtain 113.35 g of M4-1, which was analyzed by mass spectrometry, and the mass-to-charge ratio was m / z = 377.22.

[0091] (4) Synthesis of intermediate M5-1

[0092] The obtained M4-1 (113.35 g, 0.3 mol) was added to dichloromethane (1000 mL) and stirred until dissolved. Then, methanesulfonic acid (MSA) (113.35 g) was added, and the mixture was heated to 40 °C for 24 h under nitrogen protection. After the reaction was completed, the product was washed with water and concentrated to obtain the crude product. The crude product was crystallized with toluene to obtain 77.95 g of M5-1, with a yield of 75.3%. The mass-to-charge ratio was m / z = 345.87.

[0093] Examples of intermediate preparation 16-23

[0094] Examples 16 to 23 of intermediate preparations each provide an intermediate, the synthesis method of which is the same as that of intermediate M5-1. The only difference is that the raw material M1-1 in step (1) of intermediate preparation example 15 is replaced with the corresponding amount of other raw material M1 (see Table 3), and the raw material A3-1 in step (2) is replaced with the corresponding amount of other raw material A3 (see Table 3). Other conditions are the same as the synthesis method of intermediate M5-1. The intermediate is detected by mass spectrometry, and the test data is shown in Table 3 below. The yield of the intermediate is shown in Table 3.

[0095] Table 3. Mass spectrometry data and yields of raw materials and intermediates used in Examples 16-23 of intermediate preparation.

[0096]

[0097] Synthesis Example 1

[0098] This synthetic example provides a method for synthesizing compound P-1, comprising the following steps:

[0099]

[0100] (1) Ar1-1 (281.53 g, 1 mol), Ar2-1 (121.93 g, 1 mol), potassium carbonate (276.42 g, 2 mol), toluene (2400 mL), ethanol (1200 mL), and water (1200 mL) were added to the reaction flask. After adding nitrogen, the temperature was raised to 75 °C. Then, Pd(pph3)4 (3.47 g) was quickly added to the reaction flask. The temperature was maintained at 75-80 °C for 12 h to stop the reaction. After the reaction was completed, the temperature was lowered to room temperature. The reaction solution was extracted, washed with water, and concentrated to obtain a crude product. The crude product was crystallized from toluene and ethanol to obtain 265.64 g of Z1-1, with a yield of 95.3% (m / z = 278.65).

[0101]

[0102] (2) Add M1-14 (377.97 g, 0.95 mol), pinacol diborate (253.94 g, 1 mol), potassium acetate (186.47 g, 1.9 mol), and toluene (2000 mL) to the reaction flask. After adding nitrogen, raise the temperature to 75 °C. Then, quickly add Pd2(dba)3 (2.61 g, 0.00285 mol) and x-phos (2.72 g, 0.0057 mol) to the reaction flask. Maintain the temperature at 95–100 °C and react for 12 h to end the reaction. After the reaction is complete, cool to room temperature. The reaction solution is extracted, washed with water, and concentrated to obtain a crude product. After crystallization of the crude product with toluene, 414.24 g of Z1-2 is obtained, with a yield of 89.1% and m / z = 489.92.

[0103] (3) Add Z1-2 (391.5g, 0.8mol), Z1-1 (223g, 0.8mol), potassium carbonate (221.14g, 1.6mol), toluene (2500mL), ethanol (600mL), and water (600mL) to the reaction flask. After adding nitrogen, raise the temperature to 75℃. Then, quickly add Pd(pph3)4 (2.77g, 0.0024mol) to the reaction flask and maintain the temperature at 75-80℃ for 12 hours to complete the reaction. After the reaction is complete, cool to room temperature. The reaction solution is extracted, washed with water, and concentrated to obtain a crude product. The crude product is crystallized from toluene to obtain 370.68g of P-1, with a yield of 76.37% and m / z = 606.01.

[0104] Table 4. Mass spectrometry data and yields of raw materials and products used in Synthesis Examples 2–9

[0105]

[0106] Synthesis Examples 2-9

[0107] Synthesis Examples 2-9 respectively provide a method for synthesizing an OLED compound. The method of synthesis is the same as that of compound P-1. The only difference is that Ar1-1 in step (1) of Synthesis Example 1 is replaced with other Ar1 in the same amount (see Table 4), Ar2-1 in step (1) of Synthesis Example 1 is replaced with other Ar2 in the same amount (see Table 4), and M1-14 in step (2) of Synthesis Example 1 is replaced with other Ar3 in the same amount (see Table 4). Other conditions are the same as those for the synthesis of compound P-1. The synthesized compound is detected by mass spectrometry. The test data are shown in Table 4.

[0108] Synthesis Example 10

[0109] This synthetic example provides a method for synthesizing compound P-71, comprising the following steps:

[0110]

[0111] (1) Add M5-1 (311.20 g, 0.9 mol), pinacol diboronate (253.94 g, 1 mol), potassium acetate (186.47 g, 1.9 mol), and toluene (2000 mL) to the reaction flask. After adding nitrogen, raise the temperature to 75 °C. Then, quickly add Pd2(dba)3 (2.61 g, 0.00285 mol) and x-phos (2.72 g, 0.0057 mol) to the reaction flask. Maintain the temperature at 95–100 °C for 12 h to stop the reaction. After the reaction is complete, cool to room temperature. The reaction solution is extracted, washed with water, and concentrated to obtain a crude product. The crude product is crystallized in toluene to obtain 362.08 g of Z3-1, with a yield of 82.80% and m / z = 437.66.

[0112]

[0113] (2) Add Z3-1 (362.08g, 0.83mol), Ar4-1 (330.59g, 0.83mol, CAS: 894791-46-9), potassium carbonate (229.43g, 1.66mol), toluene (2800mL), ethanol (800mL), and water (800mL) to the reaction flask. After adding nitrogen, raise the temperature to 75℃, and then quickly add Pd(pph3)4 (2.89g, 0.0025mol) to the reaction flask. Maintain the temperature at 75-80℃ for 12 hours to stop the reaction. After the reaction is complete, cool to room temperature. The reaction solution is extracted, washed with water, and concentrated to obtain crude product. After crystallization of the crude product with toluene, 378.34g of P-71 is obtained, with a yield of 72.50% and m / z = 628.98.

[0114] Synthesis Examples 11-20

[0115] Synthesis Examples 11-20 respectively provide a method for synthesizing an OLED compound. The method is the same as that for the synthesis of compound P-71. The only difference is that M5-1 in step (1) of Synthesis Example 10 is replaced with other M5s of the corresponding amount (see Table 5), and Ar4-1 in step (2) of Synthesis Example 10 is replaced with other Ar4s of the corresponding amount (see Table 5). Other conditions are the same as those for the synthesis of compound P-71. The synthesized compound is subjected to mass spectrometry detection. The test data are shown in Table 5.

[0116] Table 5. Mass spectrometry data and yields of raw materials and products used in synthesis examples 11-20.

[0117]

[0118] Synthesis Example 21

[0119] This synthetic example provides a method for synthesizing OLED compound P-91, including the following steps:

[0120]

[0121] (1) Add M5-5 (327.39 g, 0.9 mol), pinacol diboronate (253.94 g, 1 mol), potassium acetate (186.47 g, 1.9 mol), and toluene (2000 mL) to the reaction flask. After adding nitrogen, raise the temperature to 75 °C. Then, quickly add Pd2(dba)3 (2.61 g, 0.00285 mol) and x-phos (2.72 g, 0.0057 mol) to the reaction flask. Maintain the temperature at 95–100 °C for 12 h to stop the reaction. After the reaction is complete, cool to room temperature. The reaction solution is extracted, washed with water, and concentrated to obtain a crude product. The crude product is crystallized from toluene to obtain 350.76 g of Z4-1, with a yield of 85.60% and m / z = 455.76.

[0122]

[0123] (2) Add Z4-1 (350.76g, 0.77mol), Ar3-2 (132.44g, 0.77mol), potassium carbonate (212.84g, 1.54mol), toluene (3500mL), ethanol (1000mL), and water (1000mL) to the reaction flask. After adding nitrogen, raise the temperature to 75℃, and then quickly add Pd(pph3)4 (2.67g, 0.0023mol) to the reaction flask. Maintain the temperature at 75-80℃ for 12 hours to complete the reaction. After the reaction is complete, cool to room temperature. The reaction solution is extracted, washed with water, and concentrated to obtain a crude product. The crude product is crystallized from toluene to obtain 312.15g of Z4-2, with a yield of 89.00% and m / z=455.66.

[0124]

[0125] (3) Add Z4-2 (312.15 g, 0.68 mol), Ar4-2 (113.70 g, 0.68 mol), sodium tert-butoxide (130.69 g, 1.36 mol), and DMSO (2800 mL) to the reaction flask. After adding nitrogen, raise the temperature to 135 °C and react for 24 h. After the reaction is complete, cool to room temperature. The reaction solution is extracted, washed with water, and concentrated to obtain a crude product. The crude product is crystallized in toluene to obtain 268.44 g of P-91, with a yield of 65.50% and m / z = 602.76.

[0126] Synthesis Example 22

[0127] Synthesis Example 22 provides a method for synthesizing an OLED compound, which is the same as the method for synthesizing compound P-91. The only difference is that M5-5 in step (1) of Synthesis Example 21 is replaced with other M5s of the same amount (see Table 6), A3-2 in step (2) of Synthesis Example 21 is replaced with 9-phenanthroline of the same amount, and Ar4-2 in step (3) of Synthesis Example 21 is replaced with other Ar4s of the same amount (see Table 6). Other conditions are the same as the method for synthesizing compound P-91. The synthesized compound was detected by mass spectrometry. The test data are shown in Table 6, and the yield is shown in Table 6.

[0128] Table 6. Mass spectrometry data and yields of raw materials and products used in Synthesis Example 22

[0129]

[0130] For other compounds whose specific synthesis methods are not listed, synthesis can be carried out by referring to the above synthesis examples and combining them with common knowledge in the field.

[0131] The specific structures of some of the materials used in the following device embodiments and device comparison examples are as follows:

[0132]

[0133]

[0134] .

[0135] Device Example 1

[0136] This embodiment of the device provides an organic electroluminescent device, the specific structure of which is as follows: Figure 1 As shown, it includes a substrate 1, an anode layer 2, a hole injection layer 3, a first hole transport layer 4, a second hole transport layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode layer 10, which are stacked in sequence.

[0137] The specific fabrication steps for organic electroluminescent devices are as follows:

[0138] 1. Clean the anode layer 2 on the transparent glass substrate (substrate 1) by ultrasonic cleaning with deionized water, acetone and ethanol for 20 minutes each, and then perform plasma treatment in an oxygen atmosphere for 5 minutes.

[0139] 2. On the anode layer 2, a hole injection layer material HI-1 with a thickness of 60 nm is deposited by vacuum evaporation. This layer serves as the first hole injection layer. Similarly, a hole injection layer material HI-2 with a thickness of 5 nm is deposited on the first hole injection layer by vacuum evaporation. This serves as the second hole injection layer, forming the hole injection layer 3.

[0140] 3. Hole transport material HT-1 with a thickness of 60 nm is deposited on hole injection layer 3 by vacuum evaporation. This layer serves as the first hole transport layer 4. Hole transport material compound HT-2 with a thickness of 10 nm is deposited on the first hole transport layer HT-1 by vacuum evaporation. This layer serves as the second hole transport layer 5.

[0141] 4. On the second hole transport layer 5, a light-emitting layer 6 is deposited by vacuum evaporation, using compound P-1 as the host material and BD-1 as the dopant material, with a doping mass ratio of 5% and a thickness of 40nm.

[0142] 5. On top of the light-emitting layer 6, hole-blocking material BPHEN is deposited by vacuum evaporation with a thickness of 5nm. This layer serves as the hole-blocking layer 7.

[0143] 6. On the hole blocking layer 7, electron transport material ET-1 with a thickness of 35nm is deposited by vacuum evaporation. This layer serves as the electron transport layer 8.

[0144] 7. On the electron transport layer 8, the electron injection material LiQ is deposited by vacuum evaporation with a thickness of 2nm. This layer serves as the electron injection layer 9.

[0145] 8. On the electron injection layer 9, cathode Al is deposited by vacuum evaporation with a thickness of 80 nm. This layer is used as the cathode conductive electrode and is called cathode layer 10.

[0146] Device Examples 2-22

[0147] Device Examples 2 to 22 each provide an organic electroluminescent device, which differs from Device Example 1 only in that the main material of the light-emitting layer 6 is different (see Table 7 for details), while other conditions are the same as those in Device Example 1.

[0148] Device Comparison Examples 1-4

[0149] Comparative Examples 1 to 4 each provide an organic electroluminescent device, which differs from Device Example 1 only in that the main material of the light-emitting layer 6 is different (see Table 7 for details), while other conditions are the same as Device Example 1.

[0150] Performance testing

[0151] The driving voltage, luminous efficiency, CIE, and lifetime LT95 of the OLED devices provided above were tested. LT95 refers to the time required for the brightness to decrease to 95% of its original brightness while maintaining an initial brightness of 1000 nits at a constant current density. The performance test results of the organic electroluminescent devices are shown in Table 7.

[0152] Table 7. Test results of the light-emitting layer substrate material and device performance used in Device Examples 2-22 and Comparative Examples 1-4.

[0153]

[0154] According to Table 7, compared with Comparative Examples 1 to 4, the device voltage prepared in Device Examples 1 to 22 was reduced by 5.32% (average), and the luminous efficiency and lifetime were improved. Therefore, the device prepared by the compound of the present invention has the advantages of lower voltage, higher luminous efficiency and longer lifetime.

[0155] The applicant declares that the detailed process flow of this invention is illustrated by the above embodiments, but this invention is not limited to the above detailed process flow, that is, it does not mean that this invention must rely on the above detailed process flow to be implemented. Those skilled in the art should understand that any improvements to this invention, equivalent substitutions of raw materials for the product of this invention, addition of auxiliary components, and selection of specific methods, etc., all fall within the protection scope and disclosure scope of this invention.

Claims

1. An OLED compound, characterized in that, The OLED compound has the structure shown in Formula I: Formula I, Among them, R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl groups having 1-30 carbon atoms, and substituted or unsubstituted C3-C groups. 30 cycloalkyl, substituted or unsubstituted C1-C 30 Any one of alkoxy, trialkylsilyl, dialkylarylsilyl, substituted or unsubstituted aryl with 6-30 carbon atoms, or substituted or unsubstituted heteroaryl with 3-30 carbon atoms.

2. The OLED compound according to claim 1, characterized in that, R1, R2, R3, R4, R5, R6, R7, R8, and R9, any two adjacent substitution positions together independently form a cyclic group, wherein the cyclic group is selected from any one of naphthalene, anthracene, phenanthrene, benzo[a]phenanthrene, fluorene, furan, thiophene, carbazole, pyridine, and pyrimidine.

3. The OLED compound according to claim 1, characterized in that, At least one of the following conditions must be met: The heteroatom of the heteroaryl group is selected from any one of N, O, and S; The halogen is F; The alkyl group having 1-30 carbon atoms is methyl or tert-butyl; The C3-C 30 The cycloalkyl group is cyclohexyl; The C1-C 30 The alkoxy group is a methoxy group.

4. The OLED compound according to claim 1, characterized in that, R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each independently selected from the following non-simple groups: 。 5. The OLED compound according to claim 4, characterized in that, When at least one of R1, R2, R3, R4, R5, R6, R7, R8, and R9 is a non-simple group, the hydrogen on each of R1, R2, R3, R4, R5, R6, R7, R8, and R9 is independently converted by deuterium, halogen, or C1-C. 10 Alkyl, C3-C 10 cycloalkyl, C6-C 20 Aryl, C3-C 20 Any substitution of a heteroaryl group.

6. The OLED compound according to claim 1, characterized in that, R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each independently selected from any one or more combinations of benzene, naphthalene, phenanthrene, benzo[a]phenanthrene, biphenyl, furan, thiophene, fluorene, and xanthene. Preferably, R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each independently selected from any of the following structures. 。 7. The OLED compound according to claim 1, characterized in that, R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each independently selected from any one or more combinations of benzene, naphthalene, phenanthrene, benzo[a]phenanthrene, biphenyl, furan, thiophene, fluorene, and xanthene that are partially or completely substituted with deuterium. Preferably, R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each independently selected from any of the following structures. 。 8. The OLED compound according to claim 1, characterized in that, The OLED compound is selected from any one of the following compounds: 。 9. The use of the OLED compound according to any one of claims 1 to 8 in the preparation of luminescent materials.

10. A light-emitting device, characterized in that, The light-emitting device includes the OLED compound according to any one of claims 1 to 8.

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