An OLED compound and application thereof, and a light-emitting device

Abstract

The application provides an OLED compound and application and a light-emitting device, and belongs to the technical field of organic photoelectric materials, wherein the OLED compound has a structure as shown in formula I, can reduce the driving voltage of an organic electroluminescent device, improve the light-emitting efficiency of the device, and prolong the service life of the device.

Description

TECHNICAL FIELD

[0001] The application belongs to the technical field of organic optoelectronic materials, and relates to an OLED compound and application thereof and a light-emitting device. BACKGROUND

[0002] As a new type of display technology, the organic electroluminescent device has the unique advantages of self-illumination, wide viewing angle, low energy consumption, high efficiency, thinness, rich colors, fast response speed, wide temperature range, low driving voltage, flexible and bendable display panel, and environmental friendliness, and can be applied to flat panel displays and a new generation of lighting.

[0003] Currently, organic electroluminescence has become a mainstream display technology, and various new materials have been developed for the preparation of organic thin film layers. However, with the development of society and technology, people have higher requirements for various properties of organic electroluminescent devices, especially in terms of luminous efficiency, service life, voltage and the like. Therefore, it is urgent to develop more types of organic thin film layer materials with higher performance to meet the higher requirements of people for organic electroluminescent devices. SUMMARY

[0004] In view of the deficiencies of the prior art, the application provides an OLED compound and application thereof and a light-emitting device, which solves the technical problem that the organic electroluminescent device cannot meet higher requirements in terms of luminous efficiency, service life and voltage performance.

[0005] To achieve the above object, the application is implemented by the following technical scheme:

[0006] In a first aspect, the application provides an OLED compound, which has a structure as shown in Formula I:

[0007]

[0008] Formula I,

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

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

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

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

[0013] the halogen is F;

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

[0015] the C3-C 30 cycloalkyl is cyclohexyl;

[0016] the C1-C 30 alkoxy is methoxy.

[0017] Preferably, R1, R2, R3, R4, R5, R6, R7, R8, 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, R9 is the non-simple group, the hydrogen on R1, R2, R3, R4, R5, R6, R7, R8, R9 is each independently substituted with any one of deuterium, halogen, C1-C 10 alkyl, C3-C 10 cycloalkyl, C6-C 20 aryl, C3-C 20 heteroaryl.

[0020] Preferably, R1, R2, R3, R4, R5, R6, R7, R8, R9 are each independently selected from any one or combination of the following: benzene, naphthalene, phenanthrene, benzophenanthrene, biphenyl, furan, thiophene, fluorene, xanthene;

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

[0022]

[0023] .

[0024] Preferably, each of said R1, R2, R3, R4, R5, R6, R7, R8, R9 is independently selected from a combination of any one or more of phenyl, naphthyl, phenanthryl, benzophenanthryl, biphenyl, furan, thiophene, fluorene, xanthene, which is partially or fully substituted with deuterium;

[0025] Preferably, each of said R1, R2, R3, R4, R5, R6, R7, R8, R9 is independently selected from any one of the following structures,

[0026] .

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

[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 application provides the OLED compound of the first aspect for use in the preparation of a light-emitting material.

[0048] In a third aspect, the present application provides a light-emitting device comprising the OLED compound of the first aspect.

[0049] Compared with the prior art, the present application has the following beneficial effects:

[0050] The OLED compound of the present application can be used for preparing an organic electroluminescent device. By designing the structure of the OLED compound, the OLED compound has excellent transport performance and light-emitting performance. When used as a light-emitting layer material, the OLED compound can reduce the driving voltage of the organic electroluminescent device, improve the light-emitting efficiency of the device, and prolong the service life of the device. BRIEF DESCRIPTION OF DRAWINGS

[0051] In order to more clearly illustrate the technical solutions in the embodiments of the present application or the prior art, the drawings needed to be used in the embodiments or prior art description will be briefly introduced below. Obviously, the drawings in the following description are only some embodiments of the present application, and other drawings can also be obtained by those skilled in the art without creative labor.

[0052] Figure 1 is a structural schematic diagram of an organic electroluminescent device provided by the device embodiment,

[0053] wherein, 1-substrate, 2-anode layer, 3-hole injection layer, 4-first hole transport layer, 5-second hole transport layer, 6-light-emitting layer, 7-hole blocking layer, 8-electron transport layer, 9-electron injection layer, 10-cathode layer. DETAILED DESCRIPTION

[0054] In order to facilitate the understanding of the present application, the present application lists the following embodiments. Those skilled in the art should understand that the embodiments are only to help understand the present application, and should not be regarded as a specific limitation on the present application.

[0055] The present application provides an OLED compound and its application, and a light-emitting device. The OLED compound has a structure as shown in formula I, which can reduce the driving voltage of the organic electroluminescent device, improve the light-emitting efficiency of the device, and prolong the service life of the device.

[0056]

[0057] (I).

[0058] The technical solutions in the embodiments of the present application are to solve the above technical problems, and the general idea is to synthesize key intermediates M1 and / or M5 first, and then synthesize target product P.

[0059] First, the synthesis of key intermediates M1 and M5 is as follows:

[0060]

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

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

[0063]

[0064] Secondly, the synthesis of target product P includes two paths, which are synthesis of general formula 1 and synthesis of general formula 2.

[0065] The synthesis of general formula 1 is as follows:

[0066]

[0067]

[0068]

[0069] Wherein, Ar' and Ar" are the same or different, and X and X' = Br, Cl.

[0070] The synthesis of general formula 2 is as follows:

[0071] .

[0072] Intermediate preparation example 1

[0073] The present intermediate preparation example provides a synthesis method of intermediate M1-1, and the synthesis steps are as follows:

[0074]

[0075] Into a reaction flask was added A1-1 (100 g, 0.46 mol), ethanol (1000 mL), and the mixture was stirred under nitrogen protection and heated to 40-50°C. Ammonia (25%-28%, 107 g) was added to the flask, and the mixture was stirred for 30 min. Hydrazine hydrate (57.57 g) was added, and the mixture was reacted at 40-50°C for 2 h. After the solid completely precipitated, the reaction system was concentrated to dryness under reduced pressure. Subsequently, A2-1 (56.17 g, 0.46 mol) and PPA (800 g) were added, and the mixture was stirred under nitrogen protection and heated to 120-130°C for 5 h. After the reaction was completed, the temperature was lowered to 20-30°C. Water (1000 mL) was slowly added to the reaction system, and the mixture was stirred until it was completely dissolved. The mixture was continuously stirred for 3 h, and the solid was precipitated. The solid was filtered, and 113.43 g of white solid M1-1 was obtained by crystallization from ethanol. GC = 99.75%, yield 85%.

[0076] The intermediate M1-1 was subjected to mass spectrometry detection, and the mass-to-charge ratio (m / z) was m / z = 290.0. The intermediate M1-1 was subjected to nuclear magnetic detection: 1H NMR (600 MHz, Chloroform-d) 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] Intermediate Preparation Examples 2-14

[0078] Intermediate Preparation Examples 2-14 respectively correspond to provide an intermediate, and the synthesis method refers to the synthesis method of intermediate M1-1, the difference is only that the raw material A1-1 in intermediate preparation example 1 is replaced by the corresponding amount of other raw material A1 (see Table 2 for details), and the raw material A2-1 is replaced by the corresponding amount of other raw material A2 (see Table 2 for details), and the other conditions are the same as the synthesis method of intermediate M1-1. The intermediate was subjected to mass spectrometry detection, and the test data are shown in Table 2. The yield of the intermediate is shown in Table 2.

[0079] Table 2 Raw materials used in intermediate preparation examples 2-14 and mass spectrometry data and yield of the intermediate

[0080]

[0081]

[0082] Intermediate Preparation Example 15

[0083] The present intermediate preparation example provides a method for synthesizing intermediate M5-1, and the synthesis steps are specifically as follows:

[0084]

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

[0086] THF (1000 mL), M1-1 (100 g, 0.34 mol) were added to a dry reaction bottle, and the bottle was cooled to -78°C under nitrogen protection, and then 2.5M n-BuLi (163.2 mL, 0.408 mol) was added dropwise. After 1h of reaction at -78°C, trimethyl borate (42.4 g, 0.408 mol) was added to the bottle, and the temperature was controlled below -78°C during the process. After the addition was completed, the reaction was continued for 2h, and then the temperature was raised to room temperature. The reaction was quenched with dilute hydrochloric acid, extracted with ethyl acetate, and washed with water until neutral. The crude product was obtained by concentration, and then refined and dried with dichloromethane to obtain 79.77g of M2-1, with a yield of 92.00%. Mass spectrometry detection was performed, and the mass-to-charge ratio was m / z = 255.18.

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

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

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

[0090] M3-1 (103.22g, 0.3mol) obtained above was added to a reaction bottle, dissolved with THF (1000mL), and then (methoxymethyl)triphenylphosphonium chloride (114.28g, 0.3mol) was added. Sodium tert-butoxide (57.66g, 0.6mol) was added to the bottle under nitrogen protection, and the temperature was controlled not to exceed 30°C during the addition. After the addition was completed, the reaction was continued for 12h, and then the reaction was stopped. The reaction liquid was quenched, extracted, washed with water, and concentrated to obtain 113.35g of M4-1. Mass spectrometry detection was performed, 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 into dichloromethane (1000 mL), stirred until dissolved, then methanesulfonic acid (MSA) (113.35 g) was added, and the temperature was raised to 40°C under nitrogen protection for 24 h. After the reaction was completed, the crude product was obtained by washing with water and concentrating. The crude product was crystallized with toluene to obtain 77.95 g of M5-1, with a yield of 75.3%. Mass spectrometry detection was performed, and the mass-to-charge ratio was m / z = 345.87.

[0093] Intermediate preparation examples 16-23

[0094] Intermediate preparation examples 16-23 respectively correspond to provide an intermediate, and the synthesis method refers to the synthesis method of intermediate M5-1, the only difference is that the raw material M1-1 in step (1) of intermediate preparation example 15 is replaced by other raw material M1 of corresponding amount of substance (see Table 3 for details), and the raw material A3-1 in step (2) is replaced by other raw material A3 of corresponding amount of substance (see Table 3 for details). The other conditions are the same as those in the synthesis method of intermediate M5-1. Mass spectrometry detection was performed on the intermediate, and the test data are shown in Table 3 below. The yield of the intermediate is shown in Table 3.

[0095] Table 3 Raw materials used in intermediate preparation examples 16-23 and mass spectrometry data and yield of the intermediate

[0096]

[0097] Synthesis example 1

[0098] The present synthesis example provides a synthesis method of compound P-1, which comprises 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 a reaction bottle. After addition was completed, the temperature was raised to 75°C under nitrogen protection, then Pd(pph3)4 (3.47 g) was rapidly added to the reaction bottle, and the temperature was maintained at 75-80°C for 12 h to complete the reaction. After the reaction was completed, the temperature was lowered to room temperature, and the reaction liquid was extracted, washed with water, and concentrated to obtain a crude product. The crude product was crystallized with toluene and ethanol to obtain 265.64 g of Z1-1, with a yield of 95.3% (m / z = 278.65).

[0101]

[0102] (2) Into a reaction flask were added M1-14 (377.97 g, 0.95 mol), bis(pinacolato)diboron (253.94 g, 1 mol), potassium acetate (186.47 g, 1.9 mol), toluene (2000 mL), and the mixture was heated to 75°C under nitrogen protection, then Pd2(dba)3 (2.61 g, 0.00285 mol) and x-phos (2.72 g, 0.0057 mol) were rapidly added to the reaction flask, and the mixture was maintained at 95-100°C for 12 h to end the reaction. After the reaction was completed, the mixture was cooled to room temperature, extracted, washed with water, and concentrated to obtain a crude product, which was crystallized from toluene to obtain 414.24 g of Z1-2, with a yield of 89.1% and m / z = 489.92.

[0103]

[0104] (3) Into a reaction flask were added Z1-2 (391.5 g, 0.8 mol), Z1-1 (223 g, 0.8 mol), potassium carbonate (221.14 g, 1.6 mol), toluene (2500 mL), ethanol (600 mL), water (600 mL), and the mixture was heated to 75°C under nitrogen protection, then Pd(pph3)4 (2.77 g, 0.0024 mol) was rapidly added to the reaction flask, and the mixture was maintained at 75-80°C for 12 h to end the reaction. After the reaction was completed, the mixture was cooled to room temperature, extracted, washed with water, and concentrated to obtain a crude product, which was crystallized from toluene to obtain 370.68 g of P-1, with a yield of 76.37% and m / z = 606.01.

[0105] Table 4. Mass spectrometry data and yield of raw materials and products used in synthesis examples 2-9

[0106]

[0107] Synthesis examples 2-9

[0108] Synthesis examples 2-9 respectively correspond to a synthesis method of an OLED compound, and the synthesis method refers to the synthesis method of compound P-1, with the difference being that synthesis example 1 step (1) Ar1-1 is replaced by other Ar1 in the corresponding amount of substance (see Table 4), synthesis example 1 step (1) Ar2-1 is replaced by other Ar2 in the corresponding amount of substance (see Table 4), and synthesis example 1 step (2) M1-14 is replaced by other Ar3 in the corresponding amount of substance (see Table 4), and other conditions are the same as the synthesis method of compound P-1. The synthesized compounds were subjected to mass spectrometry detection, and the test data are shown in Table 4.

[0109] Synthesis example 10

[0110] The synthesis example provides a synthesis method of compound P-71, which comprises the following steps:

[0111]

[0112] (1) M5-1 (311.20 g, 0.9 mol), bis(pinacolato)diboron (253.94 g, 1 mol), potassium acetate (186.47 g, 1.9 mol), toluene (2000 mL) were added into a reaction bottle, and then the reaction bottle was protected by nitrogen and heated to 75 DEG C, and then Pd2(dba)3 (2.61 g, 0.00285 mol) and x-phos (2.72, 0.0057 mol) were rapidly added into the reaction bottle, and the reaction was carried out at 95-100 DEG C for 12 h. After the reaction was completed, the reaction liquid was extracted, washed with water, and concentrated to obtain a crude product, and the crude product was crystallized from toluene to obtain 362.08 g of Z3-1, with a yield of 82.80%, m / z = 437.66;

[0113]

[0114] (2) Z3-1 (362.08 g, 0.83 mol), Ar4-1 (330.59 g, 0.83 mol, CAS: 894791-46-9), potassium carbonate (229.43 g, 1.66 mol), toluene (2800 mL), ethanol (800 mL), water (800 mL) were added into a reaction bottle, and then the reaction bottle was protected by nitrogen and heated to 75 DEG C, and then Pd(pph3)4 (2.89 g, 0.0025 mol) was rapidly added into the reaction bottle, and the reaction was carried out at 75-80 DEG C for 12 h. After the reaction was completed, the reaction liquid was extracted, washed with water, and concentrated to obtain a crude product, and the crude product was crystallized from toluene to obtain 378.34 g of P-71, with a yield of 72.50%, m / z = 628.98.

[0115] Synthesis examples 11-20

[0116] Synthesis examples 11-20 respectively provide a synthesis method of an OLED compound, and the synthesis method refers to the synthesis method of compound P-71, and the only difference is that M5-1 in step (1) of synthesis example 10 is replaced by other M5 (see Table 5) in a corresponding amount of substance, and Ar4-1 in step (2) of synthesis example 10 is replaced by other Ar4 (see Table 5) in a corresponding amount of substance, and other conditions are the same as those of the synthesis method of compound P-71. The synthesized compounds are detected by mass spectrometry, and the test data are shown in Table 5.

[0117] Table 5 Mass spectrometry data and yield of raw materials and products used in synthesis examples 11-20

[0118]

[0119] Synthesis Example 21

[0120] The present synthesis example provides a method for synthesizing an OLED compound P-91, comprising the following steps:

[0121]

[0122] (1) Into a reaction flask were added M5-5 (327.39 g, 0.9 mol), bis(pinacolato)diboron (253.94 g, 1 mol), potassium acetate (186.47 g, 1.9 mol), and toluene (2000 mL), and the mixture was heated to 75°C under nitrogen protection, followed by rapidly adding Pd2(dba)3 (2.61 g, 0.00285 mol) and x-phos (2.72 g, 0.0057 mol) to the reaction flask, and the mixture was maintained at 95-100°C for 12 h to end the reaction. After the reaction was completed, the mixture was cooled to room temperature, and the reaction solution was extracted, washed with water, and concentrated to obtain a crude product, which was crystallized from toluene to obtain 350.76 g of Z4-1 in a yield of 85.60%, m / z = 455.76.

[0123]

[0124] (2) Into a reaction flask were added Z4-1 (350.76 g, 0.77 mol), Ar3-2 (132.44 g, 0.77 mol), potassium carbonate (212.84 g, 1.54 mol), toluene (3500 mL), ethanol (1000 mL), and water (1000 mL), and the mixture was heated to 75°C under nitrogen protection, followed by rapidly adding Pd(pph3)4 (2.67 g, 0.0023 mol) to the reaction flask, and the mixture was maintained at 75-80°C for 12 h to end the reaction. After the reaction was completed, the mixture was cooled to room temperature, and the reaction solution was extracted, washed with water, and concentrated to obtain a crude product, which was crystallized from toluene to obtain 312.15 g of Z4-2 in a yield of 89.00%, m / z = 455.66;

[0125]

[0126] (3) Into a reaction flask were added 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), DMSO (2800 mL), and the mixture was heated to 135°C under nitrogen protection for 24 h. After the reaction was completed, the reaction solution was cooled to room temperature, extracted, washed with water, and concentrated to obtain a crude product. The crude product was crystallized from toluene to obtain 268.44 g of P-91 at a yield of 65.50%, m / z = 602.76.

[0127] Synthesis Example 22

[0128] Synthesis Example 22 corresponds to provide a synthesis method of an OLED compound, which synthesis method refers to the synthesis method of compound P-91, and the only difference is that M5-5 in step (1) of Synthesis Example 21 is replaced by other M5 in the corresponding amount of substance (see Table 6 for details), A3-2 in step (2) of Synthesis Example 21 is replaced by 9-phenanthrene boronic acid in the corresponding amount of substance, Ar4-2 in step (3) of Synthesis Example 21 is replaced by other Ar4 in the corresponding amount of substance (see Table 6 for details), and other conditions are the same as the synthesis method of compound P-91. The synthesized compounds were detected by mass spectrometry, and the test data are shown in Table 6, and the yield is shown in Table 6.

[0129] Table 6 Mass spectrometry data and yield of raw materials and products used in Synthesis Example 22

[0130]

[0131] Other compounds not listed in the specific synthesis method can be synthesized by referring to the above synthesis examples and combining with the common knowledge in the art.

[0132] The specific structures of some substances used in the following device examples and device comparative examples are as follows:

[0133]

[0134]

[0135] .

[0136] Device Example 1

[0137] The device example provides an organic electroluminescent device, which has a structure as shown in Figure 1 The device example provides an organic electroluminescent device, which has a structure as shown in

[0138] The specific preparation steps of the organic electroluminescent device are as follows:

[0139] 1. Clean the anode layer 2 on the transparent glass substrate (substrate 1) with deionized water, acetone and ethanol respectively by ultrasonic cleaning for 20 minutes, and then perform plasma treatment in oxygen atmosphere for 5 minutes;

[0140] 2. On the anode layer 2, a hole injection layer material HI-1 is evaporated by vacuum evaporation to a thickness of 60 nm, which serves as a first hole injection layer; similarly, a hole injection layer material HI-2 is evaporated by vacuum evaporation on the first hole injection layer to a thickness of 5 nm, which serves as a second hole injection layer, forming a hole injection layer 3;

[0141] 3. On the hole injection layer 3, a hole transport material HT-1 is evaporated by vacuum evaporation to a thickness of 60 nm, which serves as a first hole transport layer 4; on the first hole transport layer HT-1, a hole transport material compound HT-2 is evaporated by vacuum evaporation to a thickness of 10 nm, which serves as a second hole transport layer 5;

[0142] 4. On the second hole transport layer 5, a light-emitting layer 6 is evaporated 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%, to a thickness of 40 nm;

[0143] 5. On the light-emitting layer 6, a hole blocking material BPHEN is evaporated by vacuum evaporation to a thickness of 5 nm, which serves as a hole blocking layer 7;

[0144] 6. On the hole blocking layer 7, an electron transport material ET-1 is evaporated by vacuum evaporation to a thickness of 35 nm, which serves as an electron transport layer 8;

[0145] 7. On the electron transport layer 8, an electron injection material LiQ is evaporated by vacuum evaporation to a thickness of 2 nm, which serves as an electron injection layer 9;

[0146] 8. On the electron injection layer 9, a cathode Al is evaporated by vacuum evaporation to a thickness of 80 nm, which serves as a cathode conductive electrode, which is the cathode layer 10.

[0147] Device Examples 2-22

[0148] Device Examples 2-22 each provide an organic electroluminescent device, which differs from Device Example 1 only in that the host material of the light-emitting layer 6 is different (see Table 7 for details), and other conditions are the same as those of Device Example 1.

[0149] Device Comparative Examples 1-4

[0150] Device Comparative Examples 1-4 each provide an organic electroluminescent device, which differs from Device Example 1 only in that the host material of the light-emitting layer 6 is different (see Table 7 for details), and other conditions are the same as those of Device Example 1.

[0151] Performance test

[0152] The driving voltage, luminous efficiency, CIE and lifetime LT95 of the OLED devices provided above were tested; wherein LT95 refers to the time required for the luminance to drop to 95% of the original luminance while keeping the current density unchanged at the initial luminance of 1000 nit. The performance test results of the organic electroluminescent device are shown in Table 7.

[0153] Table 7 Host materials of the light-emitting layer used in Device Examples 2-22 and Device Comparative Examples 1-4 and performance test results of the devices

[0154]

[0155] According to Table 7, compared with Device Comparative Examples 1-4, the devices prepared in Device Examples 1-22 have a voltage reduction of 5.32% (average value), and the luminous efficiency and lifetime are improved, so the devices prepared by the compounds of the present application have the advantages of lower voltage, higher luminous efficiency and longer lifetime.

[0156] The applicant states that the detailed process flow of the present application is illustrated by the above examples, but the present application is not limited to the above detailed process flow, that is, it does not mean that the present application must rely on the above detailed process flow to be implemented. It should be understood by those skilled in the art that any improvement on the present application, equivalent replacement of each raw material of the product of the present application, addition of auxiliary ingredients, selection of specific modes, etc. fall within the scope of protection and disclosure of the present application.

Claims

1. An OLED compound, characterized in that, The OLED compound has the structure shown in Formula I: ； Formula I, in, R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each independently selected from hydrogen, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and... Any one of them; Or, any two adjacent substitution positions of R1, R2, R3, R4, R5, R6, R7, R8, and R9 can independently form a cyclic group, wherein the cyclic group is selected from any one of naphthyl, anthraceneyl, phenanthryl, benzo[a]phenanthryl, fluorenyl, furanyl, thiopheneyl, carbazoleyl, pyridinyl, and pyrimidinyl. The substituents of the substituted aryl group and the substituted heteroaryl group are selected from deuterium, halogens, and C1-C. 10 Alkyl, C3-C 10 cycloalkyl, C6-C 20 Aryl, C3-C 20 Any one of the heteroaryl groups; Furthermore, at least one of R1-R9 is selected from any of the following structures: ； 。 2. The OLED compound according to claim 1, characterized in that, The heteroatom of the heteroaryl group is selected from any one of N, O, and S.

3. An OLED compound, characterized in that, The OLED compound has the structure shown in Formula I: ； Formula I, in, R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each independently selected from the following groups: ,or ； ， Furthermore, at least one of R1-R9 is selected from any of the following structures: ； 。 4. An OLED compound, characterized in that, The OLED compound has the structure shown in Formula I: ； Formula I, Wherein, R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each independently selected from phenyl, naphthyl, phenanthryl, benzo[a]phenanthryl, biphenyl, furanyl, thiophene, fluorenyl, oxanthyl, or ； Any one of them, Furthermore, at least one of R1-R9 is selected from any of the following structures: ； 。 5. An OLED compound, characterized in that, The OLED compound has the structure shown in Formula I: ； Formula I, Wherein, R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each independently selected from phenyl, naphthyl, phenanthryl, benzo[a]phenanthryl, biphenyl, furanyl, thiophene, fluorenyl, oxanthyl, or [other compounds] partially or completely substituted with deuterium. ； Any one of them, Furthermore, at least one of R1-R9 is selected from any of the following structures: ； 。 6. An OLED compound, characterized in that, The OLED compound has the structure shown in Formula I: ； Formula I, in, R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each independently selected from any of the following structures. ,or ； ， Furthermore, at least one of R1-R9 is selected from any of the following structures: ； 。 7. An OLED compound, characterized in that, The OLED compound is selected from any one of the following compounds: ； ； ； ； ； ； ； ； ； ； ； ； ； 。 8. The use of an OLED compound according to any one of claims 1 to 6 or claim 7 in the preparation of luminescent materials.

9. A light-emitting device, characterized in that, The light-emitting device includes the OLED compound described in any one of claims 1 to 6 or claim 7.

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