Organic electroluminescent material based on tetramethylpyrene and organic electroluminescent device containing organic electroluminescent material

Abstract

The invention provides an organic electroluminescent material based on tetramethylpyrene and an organic electroluminescent device containing the material. The structural formula of the compound is shown in the specification: # imgabs 0 #, wherein R1 and R2 are respectively and independently groups with the following structural formula: # imgabs 1 #, r3 and R4 are respectively and independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silyl or silicon derivative groups, substituted or unsubstituted C1-C10 linear or branched alkyl, substituted or unsubstituted C6-C60 aromatic alkyl, and substituted or unsubstituted C5-C60 heteroaromatic alkyl. When the tetramethylpyrene organic electroluminescent material is applied to an organic electroluminescent device, the luminous efficiency is effectively improved under the same current density, the starting voltage of the device is reduced, the power consumption of the device is remarkably reduced, and the service life of the device is prolonged.

Description

Technical Field

[0001] The invention relates to the technical field of organic electroluminescence, and in particular to an organic electroluminescent material based on tetramethylpyrene and an organic electroluminescent device containing the material. Background Art

[0002] Organic light-emitting devices (OLED) are self-emitting devices that use the following principle: when an electric field is applied, the fluorescent material emits light through the recombination of holes injected from the positive electrode and electrons injected from the negative electrode. This self-emitting device has the characteristics of low voltage, high brightness, wide viewing angle, fast response, good temperature adaptability, etc., and is ultra-thin and can be made on flexible panels. It is widely used in mobile phones, tablet computers, televisions, lighting and other fields.

[0003] Organic electroluminescent devices are like sandwich structures, including electrode material films, and organic functional materials sandwiched between different electrode films or self-recommended. Various functional materials are superimposed on each other according to their uses to form organic electroluminescent devices. As a current device, when voltage is applied to the electrodes at both ends of the organic electroluminescent device, positive and negative charges are generated in the organic layer functional material film through the action of the electric field. The positive and negative charges are further compounded in the light-emitting layer to generate light. This process is electroluminescence.

[0004] Research on improving the performance of organic electroluminescent devices includes: reducing the driving voltage of the device, improving the luminous efficiency of the device, and increasing the service life of the device. In order to continuously improve the performance of organic electroluminescent devices, it is necessary not only to innovate the structure and manufacturing process of organic electroluminescent devices, but also to continuously research and innovate organic electrophotoelectric functional materials to create higher performance organic electroluminescent functional materials.

[0005] As far as the actual needs of the current organic electroluminescent industry are concerned, the current development of organic electroluminescent materials is far from enough and lags behind the requirements of panel manufacturers. As a material-based enterprise, it is particularly important to develop higher-performance organic functional materials.

[0006] In view of this, the present invention is proposed. Summary of the invention

[0007] In view of the above technical problems, the present invention provides an organic electroluminescent material based on tetramethylpyrene and an organic electroluminescent device containing the material.

[0008] In order to achieve the above-mentioned object of the invention, the technical solution adopted by the present invention is as follows:

[0009] An organic electroluminescent material based on tetramethylpyrene, the structural formula of which is shown below:

[0010]

[0011] The R1 and R2 are independently a group of the following structural formula:

[0012]

[0013] Among them, R3 and R4 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silane or silicon derivative group, substituted or unsubstituted C1-C10 straight or branched alkyl, substituted or unsubstituted C6-C60 aromatic hydrocarbon group, substituted or unsubstituted C5-C60 heteroaromatic hydrocarbon group.

[0014] Preferably, R3 and R4 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl.

[0015] Preferably, the methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl is unsubstituted or at least one hydrogen atom is substituted by deuterium or halogen.

[0016] Preferably, the organic electroluminescent material is one of the following compounds:

[0017]

[0018]

[0019]

[0020]

[0021]

[0022] Application of the above organic electroluminescent material in the preparation of organic electroluminescent devices.

[0023] Furthermore, the present invention also provides an organic electroluminescent device, comprising: an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode stacked in sequence; the electron transport layer contains at least one of the above-mentioned organic electroluminescent materials.

[0024] Furthermore, the present invention also provides an organic electroluminescent display device comprising the organic electroluminescent device.

[0025] Furthermore, the present invention also provides an organic electroluminescent lighting device comprising the organic electroluminescent device.

[0026] The room temperature described in the present invention is 25±5°C.

[0027] Compared with the prior art, the beneficial effects of the present invention are as follows:

[0028] 1. The tetramethylpyrene-based organic electroluminescent material designed by the present invention increases the conjugation effect of the material molecules in the structural design, improves the rigidity of the material molecules, and further improves the thermal stability of the material and the luminescence efficiency of the material molecules.

[0029] 2. The introduction of deuterated structure greatly improves the luminous efficiency of material molecules by more than 30%, and further increases the service life of luminescent materials. BRIEF DESCRIPTION OF THE DRAWINGS

[0030] Figure 1 A schematic diagram of the structure of an organic electroluminescent device provided by the present invention;

[0031] The numbers in the figure represent:

[0032] 1- cathode, 2- electron injection layer, 3- electron transport layer, 4- light emitting layer, 5- hole transport layer, 6- hole injection layer, 7- anode.

[0033] Figure 2 is the HPLC spectrum of compound 1 prepared in Example 1 of the present invention;

[0034] Figure 3 is the DSC spectrum of compound 1 prepared in Example 1 of the present invention;

[0035] Figure 4 This is the TGA spectrum of compound 1 prepared in Example 1 of the present invention. DETAILED DESCRIPTION

[0036] If the specific conditions are not specified in the examples, the experiments were carried out under conventional conditions or conditions recommended by the manufacturer. If the manufacturers of the reagents or instruments are not specified, they are all conventional products that can be purchased commercially.

[0037] Embodiment 1:

[0038]

[0039] The synthesis method of the organic electroluminescent material (1) is as follows:

[0040]

[0041] (1) Compound 1-a (5 g, 258.14 g / mol, 19.37 mmol), dichloromethane (50 g, 10 times the mass of compound A) were added to a three-necked flask, and concentrated sulfuric acid (0.05 eq, 18.4 mol / L, 0.05 ml, 0.97 mmol) was slowly added. After the addition was completed, N-bromosuccinimide (2.1 eq, 177.98 g / mol, 7.24 g, 40.68 mmol) was added in multiple portions under stirring at room temperature. After the addition was completed, the reaction was stirred at room temperature for 12 hours. After the reaction was completed by HPLC monitoring, the reaction was stopped, and ethanol (200 g, 40 times the mass of compound 1-a) was slowly added to the reaction solution to precipitate a solid. The solid was filtered to obtain a filter cake. The filter cake was boiled in toluene for 3 hours and then cooled to room temperature and filtered to obtain compound 1-b (5.46 g, yield 68.2%), MS (EI): 413 (M+).

[0042]

[0043] Compound 1-b (5 g, 413.96 g / mol, 12.08 mmol), compound 1-c (2.1 eq, 6.04 g, 238.09 g / mol, 25.36 mmol) and sodium carbonate (4 eq, 5.12 g, 105.99 g / mol, 48.31 mmol) were added to ethylene glycol diamine ether (100 g, 20 times the mass of compound 1-b) and water (100 g, 20 times the mass of compound 1-b), and stirred to mix. Tri(o-tolyl)phosphine (3% eq, 0.11 g, 304.37 g / mol, 0.36 mmol) and palladium(II) acetate (1% eq, 0.027 g, 224.51 g / mol, 0.12 mmol) were added in sequence, and the temperature was raised to reflux for 15 h. The organic phase was separated, washed with water, and concentrated under reduced pressure. After purification by column chromatography, the organic electroluminescent material (1) (6.53 g, yield 84.2%) was obtained, MS (EI): 642 (M+).

[0044] Embodiment 2:

[0045]

[0046] The synthesis method of the organic electroluminescent material (4) is as follows:

[0047]

[0048] Compound 2-a (5 g, 413.96 g / mol, 12.08 mmol), compound 2-b (2.1 eq, 7.11 g, 280.14 g / mol, 25.36 mmol) and sodium carbonate (4 eq, 5.12 g, 105.99 g / mol, 48.31 mmol) were added to ethylene glycol diamine ether (100 g, 20 times the mass of compound 2-b) and water (100 g, 20 times the mass of compound 2-b), and stirred to mix. Tri(o-tolyl)phosphine (3% eq, 0.11 g, 304.37 g / mol, 0.36 mmol) and palladium(II) acetate (1% eq, 0.027 g, 224.51 g / mol, 0.12 mmol) were added in sequence, and the temperature was raised to reflux for 15 h. The organic phase was separated, washed with water, and concentrated under reduced pressure. After purification by column chromatography, an organic electroluminescent material (4) (7.5 g, yield 85.5%) was obtained, MS (EI): 726 (M+).

[0049] Embodiment 3:

[0050]

[0051] The synthesis method of the organic electroluminescent material (5) is as follows:

[0052]

[0053] Compound 3-a (5 g, 413.96 g / mol, 12.08 mmol), compound 3-b (2.1 eq, 7.61 g, 300.11 g / mol, 25.36 mmol) and sodium carbonate (4 eq, 5.12 g, 105.99 g / mol, 48.31 mmol) were added to ethylene glycol diamine ether (100 g, 20 times the mass of compound 3-b) and water (100 g, 20 times the mass of compound 3-b), and stirred to mix. Tri(o-tolyl)phosphine (3% eq, 0.11 g, 304.37 g / mol, 0.36 mmol) and palladium(II) acetate (1% eq, 0.027 g, 224.51 g / mol, 0.12 mmol) were added in sequence, and the temperature was raised to reflux for 15 h. The organic phase was separated, washed with water, and concentrated under reduced pressure. After purification by column chromatography, the organic electroluminescent material (5) (7.71 g, yield 83.3%) was obtained, MS (EI): 766 (M+).

[0054] Embodiment 4:

[0055]

[0056] The synthesis method of the organic electroluminescent material (23) is as follows:

[0057]

[0058] Compound 4-a (5 g, 413.96 g / mol, 12.08 mmol), compound 4-b (2.1 eq, 6.12 g, 241.11 g / mol, 25.36 mmol) and sodium carbonate (4 eq, 5.12 g, 105.99 g / mol, 48.31 mmol) were added to ethylene glycol diamine ether (100 g, 20 times the mass of compound 4-b) and water (100 g, 20 times the mass of compound 4-b), stirred and mixed, and then Tri(o-tolyl)phosphine (3% eq, 0.11 g, 304.37 g / mol, 0.36 mmol) and palladium(II) acetate (1% eq, 0.027 g, 224.51 g / mol, 0.12 mmol) were added in sequence, and the temperature was raised to reflux for 15 h. The organic phase was separated, washed with water, and concentrated under reduced pressure. After purification by column chromatography, an organic electroluminescent material (23) (6.74 g, yield 86.1%) was obtained, MS (EI): 648 (M+).

[0059] Embodiment 5:

[0060]

[0061] The synthesis method of the organic electroluminescent material (30) is as follows:

[0062]

[0063] Compound 5-a (5 g, 413.96 g / mol, 12.08 mmol), compound 5-b (2.1 eq, 9.54 g, 376.14 g / mol, 25.36 mmol) and sodium carbonate (4 eq, 5.12 g, 105.99 g / mol, 48.31 mmol) were added to ethylene glycol diamine ether (100 g, 20 times the mass of compound 5-a) and water (100 g, 20 times the mass of compound 5-a), stirred and mixed, and then Tri(o-tolyl)phosphine (3% eq, 0.11 g, 304.37 g / mol, 0.36 mmol) and palladium(II) acetate (1% eq, 0.027 g, 224.51 g / mol, 0.12 mmol) were added in sequence, and the temperature was raised to reflux for 15 h. The organic phase was separated, washed with water, and concentrated under reduced pressure. After purification by column chromatography, an organic electroluminescent material (30) (8.89 g, yield 80.2%) was obtained, MS (EI): 918 (M+).

[0064] Embodiment 6:

[0065]

[0066] The synthesis method of the organic electroluminescent material (34) is as follows:

[0067]

[0068] Compound 6-a (5 g, 413.96 g / mol, 12.08 mmol), compound 6-b (2.1 eq, 7.66 g, 302.1 g / mol, 25.36 mmol) and sodium carbonate (4 eq, 5.12 g, 105.99 g / mol, 48.31 mmol) were added to ethylene glycol diamine ether (100 g, 20 times the mass of compound 6-a) and water (100 g, 20 times the mass of compound 6-a), stirred and mixed, and then Tri(o-tolyl)phosphine (3% eq, 0.11 g, 304.37 g / mol, 0.36 mmol) and palladium(II) acetate (1% eq, 0.027 g, 224.51 g / mol, 0.12 mmol) were added in sequence, the temperature was raised to reflux for 15 h, the organic phase was separated, washed with water and concentrated under reduced pressure, and then purified by column chromatography to obtain an organic electroluminescent material (34) (7.2 g, yield 77.4%), MS (EI): 770 (M+).

[0069] Embodiment 7:

[0070]

[0071] The synthesis method of the organic electroluminescent material (49) is as follows:

[0072]

[0073] Compound 7-a (5 g, 413.96 g / mol, 12.08 mmol), compound 7-b (2.1 eq, 6.01 g, 237.1 g / mol, 25.36 mmol) and sodium carbonate (4 eq, 5.12 g, 105.99 g / mol, 48.31 mmol) were added to ethylene glycol diamine ether (100 g, 20 times the mass of compound 7-a) and water (100 g, 20 times the mass of compound 7-a), stirred and mixed, and then Tri(o-tolyl)phosphine (3% eq, 0.11 g, 304.37 g / mol, 0.36 mmol) and palladium(II) acetate (1% eq, 0.027 g, 224.51 g / mol, 0.12 mmol) were added in sequence, and the temperature was raised to reflux for 15 h. The organic phase was separated, washed with water, and concentrated under reduced pressure. After purification by column chromatography, an organic electroluminescent material (49) (5.55 g, yield 71.8%) was obtained, MS (EI): 640 (M+).

[0074] Embodiment 8:

[0075]

[0076] The synthesis method of the organic electroluminescent material (57) is as follows:

[0077]

[0078] Compound 8-a (5 g, 413.96 g / mol, 12.08 mmol), compound 8-b (2.1 eq, 7.61 g, 300.11 g / mol, 25.36 mmol) and sodium carbonate (4 eq, 5.12 g, 105.99 g / mol, 48.31 mmol) were added to ethylene glycol diamine ether (100 g, 20 times the mass of compound 8-a) and water (100 g, 20 times the mass of compound 8-a), stirred and mixed, and then Tri(o-tolyl)phosphine (3% eq, 0.11 g, 304.37 g / mol, 0.36 mmol) and palladium(II) acetate (1% eq, 0.027 g, 224.51 g / mol, 0.12 mmol) were added in sequence, and the temperature was raised to reflux for 15 h. The organic phase was separated, washed with water, and concentrated under reduced pressure. After purification by column chromatography, an organic electroluminescent material (57) (6.87 g, yield 74.2%) was obtained, MS (EI): 766 (M+).

[0079] Embodiment 9:

[0080]

[0081] The synthesis method of the organic electroluminescent material (59) is as follows:

[0082]

[0083] Compound 9-a (5 g, 413.96 g / mol, 12.08 mmol), compound 9-b (2.1 eq, 6.09 g, 240.11 g / mol, 25.36 mmol) and sodium carbonate (4 eq, 5.12 g, 105.99 g / mol, 48.31 mmol) were added to ethylene glycol diamine ether (100 g, 20 times the mass of compound 9-a) and water (100 g, 20 times the mass of compound 9-a), stirred and mixed, and then Tri(o-tolyl)phosphine (3% eq, 0.11 g, 304.37 g / mol, 0.36 mmol) and palladium(II) acetate (1% eq, 0.027 g, 224.51 g / mol, 0.12 mmol) were added in sequence, the temperature was raised to reflux for 15 h, the organic phase was separated, washed with water and concentrated under reduced pressure, and then purified by column chromatography to obtain an organic electroluminescent material (59) (5.67 g, yield 72.7%), MS (EI): 646 (M+).

[0084] Embodiment 10:

[0085]

[0086] The synthesis method of the organic electroluminescent material (73) is as follows:

[0087]

[0088] Compound 10-a (5 g, 413.96 g / mol, 12.08 mmol), compound 10-b (2.1 eq, 6.01 g, 237.1 g / mol, 25.36 mmol) and sodium carbonate (4 eq, 5.12 g, 105.99 g / mol, 48.31 mmol) were added to ethylene glycol diamine ether (100 g, 20 times the mass of compound 10-a) and water (100 g, 20 times the mass of compound 10-a), and stirred to mix. Then tri(o-tolyl)phosphine (3% eq, 0.11 g, 304.37 g / mol, 0.36 mmol) and palladium(II) acetate (1% eq, 0.027 g, 224.51 g / mol, 0.12 mmol) were added in sequence. The temperature was raised to reflux for 15 h. The organic phase was separated, washed with water and concentrated under reduced pressure. After purification by column chromatography, the organic electroluminescent material (73) (6.83 g, yield 88.3%) was obtained, MS (EI): 640 (M+).

[0089] Embodiment 11:

[0090]

[0091] The synthesis method of the organic electroluminescent material (87) is as follows:

[0092]

[0093] Compound 11-a (5 g, 413.96 g / mol, 12.08 mmol), compound 11-b (2.1 eq, 6.72 g, 265.13 g / mol, 25.36 mmol) and sodium carbonate (4 eq, 5.12 g, 105.99 g / mol, 48.31 mmol) were added to ethylene glycol diamine ether (100 g, 20 times the mass of compound 11-a) and water (100 g, 20 times the mass of compound 11-a), and stirred to mix. Then tri(o-tolyl)phosphine (3% eq, 0.11 g, 304.37 g / mol, 0.36 mmol) and palladium(II) acetate (1% eq, 0.027 g, 224.51 g / mol, 0.12 mmol) were added in sequence. The temperature was raised to reflux for 15 h. The organic phase was separated, washed with water and concentrated under reduced pressure. After purification by column chromatography, the organic electroluminescent material (87) (6.81 g, yield 82.2%) was obtained, MS (EI): 696 (M+).

[0094] Embodiment 12:

[0095]

[0096] The synthesis method of the organic electroluminescent material (97) is as follows:

[0097]

[0098] (1) Compound 12-a (5 g, 258.14 g / mol, 19.37 mmol), dichloromethane (50 g, 10 times the mass of compound 12-a) were added to a three-necked flask, and concentrated sulfuric acid (0.05 eq, 18.4 mol / L, 0.05 ml, 0.97 mmol) was slowly added. After the addition was completed, N-bromosuccinimide (2.1 eq, 177.98 g / mol, 7.24 g, 40.68 mmol) was added in multiple portions under stirring at room temperature. After the addition was completed, the reaction was stirred at room temperature for 12 hours. After the reaction was completed by HPLC monitoring, the reaction was stopped, and ethanol (200 g, 40 times the mass of compound 12-a) was slowly added to the reaction solution to precipitate a solid. The solid was filtered to obtain a filter cake. The filter cake was boiled in toluene for 3 hours and then cooled to room temperature and filtered to obtain compound 12-b (6.46 g, yield 80.8%), MS (EI): 413 (M+).

[0099]

[0100] (2) Compound 12-b (5 g, 413.96 g / mol, 12.08 mmol), compound 12-c (2.1 eq, 6.04 g, 238.09 g / mol, 25.36 mmol) and sodium carbonate (4 eq, 5.12 g, 105.99 g / mol, 48.31 mmol) were added to ethylene glycol diamine ether (100 g, 20 times the mass of compound 12-b) and water (100 g, 20 times the mass of compound 12-b), and stirred. After mixing, tri(o-tolyl)phosphine (3% eq, 0.11 g, 304.37 g / mol, 0.36 mmol) and palladium(II) acetate (1% eq, 0.027 g, 224.51 g / mol, 0.12 mmol) were added in sequence. The temperature was raised to reflux for 15 h. The organic phase was separated, washed with water and concentrated under reduced pressure. After purification by column chromatography, the organic electroluminescent material (97) (6.6 g, yield 85.1%) was obtained, MS (EI): 642 (M+).

[0101] Embodiment 13:

[0102]

[0103] The synthesis method of the organic electroluminescent material (101) is as follows:

[0104]

[0105] Compound 13-a (5 g, 413.96 g / mol, 12.08 mmol), compound 13-b (2.1 eq, 7.61 g, 300.11 g / mol, 25.36 mmol) and sodium carbonate (4 eq, 5.12 g, 105.99 g / mol, 48.31 mmol) were added to ethylene glycol diamine ether (100 g, 20 times the mass of compound 13-a) and water (100 g, 20 times the mass of compound 13-a), and stirred to mix. Then tri(o-tolyl)phosphine (3% eq, 0.11 g, 304.37 g / mol, 0.36 mmol) and palladium(II) acetate (1% eq, 0.027 g, 224.51 g / mol, 0.12 mmol) were added in sequence. The temperature was raised to reflux for 15 h. The organic phase was separated, washed with water and concentrated under reduced pressure. After purification by column chromatography, the organic electroluminescent material (101) (7.67 g, yield 82.9%) was obtained. MS (EI): 766 (M+).

[0106] Embodiment 14:

[0107]

[0108] The synthesis method of the organic electroluminescent material (108) is as follows:

[0109]

[0110] Compound 14-a (5 g, 413.96 g / mol, 12.08 mmol), compound 14-b (2.1 eq, 7.34 g, 289.19 g / mol, 25.36 mmol) and sodium carbonate (4 eq, 5.12 g, 105.99 g / mol, 48.31 mmol) were added to ethylene glycol diamine ether (100 g, 20 times the mass of compound 14-a) and water (100 g, 20 times the mass of compound 14-a), and stirred to mix. Then tri(o-tolyl)phosphine (3% eq, 0.11 g, 304.37 g / mol, 0.36 mmol) and palladium(II) acetate (1% eq, 0.027 g, 224.51 g / mol, 0.12 mmol) were added in sequence. The temperature was raised to reflux for 15 h. The organic phase was separated, washed with water and concentrated under reduced pressure. After purification by column chromatography, the organic electroluminescent material (108) (7.42 g, yield 82.6%) was obtained. MS (EI): 744 (M+).

[0111] Embodiment 15:

[0112]

[0113] The synthesis method of the organic electroluminescent material (114) is as follows:

[0114]

[0115] Compound 15-a (5 g, 413.96 g / mol, 12.08 mmol), compound 15-b (2.1 eq, 9.54 g, 376.14 g / mol, 25.36 mmol) and sodium carbonate (4 eq, 5.12 g, 105.99 g / mol, 48.31 mmol) were added to ethylene glycol diamine ether (100 g, 20 times the mass of compound 15-a) and water (100 g, 20 times the mass of compound 15-a), and stirred to mix. Then tri(o-tolyl)phosphine (3% eq, 0.11 g, 304.37 g / mol, 0.36 mmol) and palladium(II) acetate (1% eq, 0.027 g, 224.51 g / mol, 0.12 mmol) were added in sequence. The temperature was raised to reflux for 15 h. The organic phase was separated, washed with water and concentrated under reduced pressure. After purification by column chromatography, the organic electroluminescent material (114) (8.24 g, yield 74.3%) was obtained, MS (EI): 918 (M+).

[0116] Material property test:

[0117] The thermal stability of the organic electroluminescent materials 1, 4, 5, 23, 30, 34, 49, 57, 59, 73, 87, 97, 101, 108, 114, PBD and p-EtAZ of the present invention was tested using TGA (TGA-1500). The T95% data (T95% temperature refers to the temperature at which the weight loss is 5% in a nitrogen atmosphere) obtained by the test are shown in Table 1 below.

[0118] Table 1:

[0119]

[0120]

[0121] It can be seen from the above data that the thermal stability of the organic electroluminescent material of the present invention is better than that of the control examples ETL-1 and ETL-2. Good thermal stability is more conducive to the use of the material and can greatly improve the lifespan and luminous efficiency of the organic electroluminescent device prepared using the material, which plays a very positive role in the marketization of OLED.

[0122] Device performance test:

[0123] Application Example 1:

[0124] ITO was used as the reflective layer anode substrate material, and its surface was treated with water, acetone, and N2 plasma in sequence;

[0125] On the ITO anode substrate, HAT-CN with a thickness of 10 nm is deposited to form a hole injection layer (HIL); NPD is evaporated on the hole injection layer (HIL) to form a hole transport layer (HTL) with a thickness of 120 nm; ADN is used as a blue light host material and BD-1 is used as a blue light doping material (the amount of BD-1 is 5% of the weight of ADN) to evaporate at different rates on the hole transport layer (HTL) to form a luminescent layer with a thickness of 30 nm; the organic electroluminescent material 1 of the present invention is evaporated on the luminescent layer to obtain an electron transport layer (ETL) with a thickness of 35 nm, and LiQ with a thickness of 2 nm is evaporated on the electron transport layer (ETL) to form an electron injection layer (EIL); thereafter, magnesium (Mg) and silver (Ag) are mixed and evaporated in a ratio of 9:1 to obtain a cathode with a thickness of 15 nm, and DNTPD with a thickness of 50 nm is deposited on the above cathode sealing layer. In addition, a UV curable adhesive and a sealing film (seal film) containing a dehumidifier are formed on the surface of the cathode. cap) to protect the organic electroluminescent device from being affected by oxygen or moisture in the atmosphere. Thus, the organic electroluminescent device is prepared.

[0126]

[0127] Application Example 2-15

[0128] The organic electroluminescent materials 4, 5, 23, 30, 34, 49, 57, 59, 73, 87, 97, 101, 108, and 114 in Examples 2-15 of the present invention are respectively used as hole transport materials, and the other parts are consistent with Application Example 1, thereby manufacturing organic electroluminescent devices of Application Examples 2-14.

[0129] Comparative Examples 1 and 2

[0130] The difference between the control examples 1 and 2 and the application example 1 is that PBD and p-EtAZ are used as electron transport materials, and the rest is the same as the application example 1.

[0131] The characteristics of the organic electroluminescent device manufactured in the above application example and the organic electroluminescent device manufactured in the control example were measured under the condition of a current density of 10 mA / cm2. The results are shown in Table 2.

[0132] Table 2:

[0133]

[0134] As shown in Table 2 above, when the organic electroluminescent material of the present invention is applied to an organic electroluminescent device, the luminous efficiency is improved to a certain extent under the same current density, and the starting voltage of the device is reduced, the power consumption of the device is relatively reduced, and the life of the device is correspondingly increased.

Claims

1. An organic electroluminescent material based on tetramethylpyrene, the structural formula of which is as follows: The R1 and R2 are independently a group of the following structural formula: in, R3 and R4 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silane or silicon derivative group, substituted or unsubstituted C1-C10 straight or branched alkyl group, substituted or unsubstituted C6-C60 aromatic hydrocarbon group, substituted or unsubstituted C5-C60 heteroaromatic hydrocarbon group.

2. The organic electroluminescent material according to claim 1, characterized in that: R3 and R4 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silyl or silicon derivative group, substituted or unsubstituted C1-C10 straight or branched alkyl group, substituted or unsubstituted C6-C40 aromatic hydrocarbon group, substituted or unsubstituted C5-C40 heteroaromatic hydrocarbon group.

3. The organic electroluminescent material according to claim 2, characterized in that: R3 and R4 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silyl or silicon derivative group, substituted or unsubstituted C1-C10 straight or branched alkyl group, substituted or unsubstituted C6-C20 aromatic hydrocarbon group, substituted or unsubstituted C5-C20 heteroaromatic hydrocarbon group.

4. The organic electroluminescent material according to claim 3, characterized in that: R3 and R4 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl.

5. The organic electroluminescent material according to claim 3, characterized in that: R3 and R4 are each independently methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl, wherein the methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl is unsubstituted or at least one hydrogen therein is substituted by deuterium or halogen.

6. The organic electroluminescent material according to claim 1, characterized in that: The organic electroluminescent material is one of the following compounds:

7. Use of the organic electroluminescent material according to any one of claims 1 to 6 in the preparation of an organic electroluminescent device.

8. An organic electroluminescent device, comprising: A structure in which an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode are stacked in sequence; the electron transport layer contains at least one organic electroluminescent material as described in claims 1-6.

9. An organic electroluminescent display device, characterized in that: Contains the organic electroluminescent device as claimed in claim 8.

10. An organic electroluminescent lighting device, characterized in that: Contains the organic electroluminescent device as claimed in claim 8.

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