Compounds and organic electroluminescent devices and display devices

Abstract

The present application relates to the field of electroluminescence, and discloses a compound, an organic electroluminescent device, and a display device. The structural formula of the compound is shown in formula (I): The organic electroluminescent device using the material of the compound of the present application has a lower driving voltage and a higher current efficiency.

Description

Technical Field

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

[0002] Currently, organic electroluminescent (OLED) display technology has been applied in smart phones, tablet computers and other fields, and will be further expanded to large-size application fields such as televisions. In the past 30 years of development, people have developed various OLED materials with excellent performance, and through different designs of device structures and optimization of device performance such as life and efficiency, the commercialization process of OLED has been accelerated, making OLED widely used in the display and lighting fields.

[0003] However, the huge gap between the external quantum efficiency and internal quantum efficiency of OLEDs has greatly restricted the development of OLEDs. One of the most important factors is that the efficiency of the device has not yet reached the ideal level. This is due to the mode loss of the substrate, the loss of the surface plasmon and the waveguide effect, which confines most of the light inside the light-emitting device, thereby reducing the luminous efficiency of the device. Improving the luminous efficiency of the device and using light extraction materials is one of the effective methods. The light extraction layer (Capping Layer, CPL) can effectively improve the light extraction efficiency of the device by reducing the surface plasma effect of the metal electrode and adjusting the light extraction direction and light extraction efficiency, thereby improving the luminous efficiency of the device. At present, the types of light extraction materials are relatively single, and the effects are not ideal. Developing more effective light extraction materials is one of the more severe challenges facing OLED workers.

[0004] In addition, the selection of light-emitting layer and other organic functional layer materials also has a significant impact on the current efficiency and driving voltage of the device, and functional layer materials with higher performance are still being explored.

[0005] Therefore, in order to meet people's higher requirements for OLED devices, the field is in urgent need of developing more types of OLED materials with higher performance. Summary of the invention

[0006] The present application discloses a carbazole compound, an organic electroluminescent device and a display device. The organic electroluminescent device using the material of the compound of the present application has a lower driving voltage and a higher current efficiency.

[0007] In order to achieve the above objectives, this application provides the following technical solutions:

[0008] A compound, the structural formula of the compound is as shown in formula (I),

[0009]

[0010] Wherein, m, n are selected from 0 or 1;

[0011] A, B, Ar 3 Each is independently selected from an aromatic group containing 6 to 40 carbon atoms, wherein the hydrogen in the aromatic group containing 6 to 40 carbon atoms may be replaced by R;

[0012] Ar 1 is selected from formula (II), wherein R 1 ~R 10 At least one is absent, and the corresponding carbon atom is connected to the N atom or A in formula (I); X is selected from oxygen or sulfur;

[0013] Ar 2 Selected from one of the structures shown in A-1 to A-7 below or the structure shown in formula (II),

[0014]

[0015] f, e are selected from 0 or 1, and at least one of them is selected from 1;

[0016] Any carbon atom in A-1 to A-7 that is sp2 hybridized and connected to only two carbon atoms can be used as a connection site to connect to N or B in formula (I);

[0017] The hydrogen in A-1 to A-7 may be replaced by one or more Rs;

[0018] R and R 1 ~R 14 Each is independently selected from hydrogen, deuterium, F, CN, an alkyl group containing 1 to 20 carbon atoms, an alkoxy group containing 1 to 20 carbon atoms or an aromatic group containing 6 to 40 carbon atoms.

[0019] Furthermore, A, B, Ar 3 Selected from benzene, biphenyl, naphthalene, anthracene, phenanthrene, fluoranthene, triphenylene, fluorene, spirofluorene, pyrene, benzanthracene, benzofluorene, naphthoanthracene, naphthofluorene, dibenzanthracene, dibenzofluorene, hydrogenated benzanthracene, indenofluorene, and benzindenofluorene.

[0020] Furthermore, the aromatic group of 6 to 40 carbon atoms is selected from benzene, biphenyl, naphthalene, anthracene, phenanthrene, fluoranthene, triphenylene, fluorene, spirofluorene, pyrene, benzanthracene, benzofluorene, naphthoanthracene, naphthofluorene, dibenzanthracene, dibenzofluorene, hydrogenated benzanthracene, indenofluorene, and benzindenofluorene.

[0021] Furthermore, the structure of the compound is:

[0022]

[0023] Furthermore, the structure of the compound is:

[0024]

[0025] Furthermore, R 1 and R 10 Each is independently selected from one of F, CN, methoxy, phenyl or biphenyl.

[0026] Further, the compound is selected from one of the structural formulas 1-162, wherein the compound of structural formula 1-81 is as follows:

[0027]

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034] The compounds of structural formulae 82 to 162 are obtained by replacing O with S in the compounds of structural formulae 1 to 81, respectively.

[0035] An organic electroluminescent device comprises the compound described in the present application.

[0036] A display device includes the organic electroluminescent device provided in the present application.

[0037] The technical solution of this application produces the following beneficial effects:

[0038] The compound represented by formula (I) of the present application is a new compound and can be used in organic electroluminescent devices as HTL and CPL materials. In addition, the OLED device prepared using the compound material represented by formula (I) of the present application has low driving voltage and high luminous efficiency. DETAILED DESCRIPTION

[0039] The following will be combined with the embodiments of the present application to clearly and completely describe the technical solutions in the embodiments of the present application. Obviously, the described embodiments are only part of the embodiments of the present application, not all of the embodiments. Based on the embodiments in the present application, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of this application.

[0040] It should be noted that: in this application, if there is no special description, all the embodiments and preferred implementation methods mentioned herein can be combined with each other to form a new technical solution. In this application, if there is no special description, all the technical features and preferred features mentioned herein can be combined with each other to form a new technical solution. In this application, if there is no special description, percentage (%) or part refers to the weight percentage or weight part relative to the composition. In this application, if there is no special description, the components or their preferred components involved can be combined with each other to form a new technical solution. In this application, unless otherwise specified, the numerical range "a-b" represents an abbreviation of any real number combination between a and b, where a and b are both real numbers. For example, the numerical range "6-22" means that all real numbers between "6-22" have been listed in this article, and "6-22" is just an abbreviation of these numerical combinations. The "range" disclosed in this application can be one or more lower limits and one or more upper limits in the form of lower limits and upper limits. In this application, unless otherwise specified, each reaction or operation step can be carried out sequentially or not in sequence. Preferably, the reaction method in this article is carried out sequentially.

[0041] Unless otherwise specified, the professional and scientific terms used herein are the same as those familiar to those skilled in the art. In addition, any method or material similar or equivalent to the described content may also be applied to the present application.

[0042] Synthesis Example 1 Synthesis of Compound 1

[0043] (1) Synthesis of intermediate M-1

[0044]

[0045] In a 250 ml three-necked flask, under nitrogen protection, add 100 ml of dry toluene, 1.69 g (0.01 mol) of 4-aminobiphenyl, 3.23 g (0.01 mol) of 9-bromo-7,7-dimethyl-7H-benzo[c]fluorene, 0.0575 g (0.0001 mol) of Pd(dba)2 (bis(dibenzylideneacetonepalladium), 0.4 g (0.0002 mol) of a toluene solution containing 10% tri-tert-butylphosphine, and 1.44 g (0.015 mol) of sodium tert-butoxide. Heat to 60°C for reaction for 12 hours, cool, add water to separate, wash the organic layer with water until neutral, dry with magnesium sulfate, filter to remove magnesium sulfate, concentrate to dryness, and recrystallize with a mixed solvent of toluene and methanol to obtain 3.8 g of the compound shown in M-1.

[0046] The compound shown in M-1 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 411.

[0047] (2) Synthesis of the compound represented by formula 1

[0048]

[0049] In a 500 ml three-necked flask, under nitrogen protection, add 200 ml of dry toluene, 4.11 g (0.01 mol) of the compound shown in M-1, 2.97 g (0.01 mol) of 3-bromobenzo[kl]xanthene, 0.0575 g (0.0001 mol) of Pd(dba)2 (bis(dibenzylideneacetonepalladium), 0.4 g (0.0002 mol) of a toluene solution containing 10% tri-tert-butylphosphine, and 1.44 g (0.015 mol) of sodium tert-butoxide. Heat to reflux for 6 hours, cool, add water to separate, wash the organic layer with water until neutral, dry with magnesium sulfate, filter to remove magnesium sulfate, concentrate to dryness, separate by silica gel column chromatography, and elute with petroleum ether to obtain 5.7 g of the compound shown in Formula 1.

[0050] The compound represented by Formula 1 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 627.

[0051] The compound represented by Formula 1 was subjected to NMR detection, and the data analysis was as follows: 1H-NMR (Bruker Company, Switzerland, AvanceⅡ400MHz NMR spectrometer, CDCl3), δ8.84 (m, 1H), δ8.21 (d, 1H), δ8.06 (m, 1H), δ7.97 (m, 1H), δ7.79~7.72 (m, 3H), δ7.66 (d, 1H), δ7.64 (m, 1H), δ7.60~7.30 (m, 11H), δ7.29~7.13 (m, 5H), δ7.11 (d, 1H), δ6.41 (m, 1H), δ1.76 (s, 6H).

[0052] Synthesis Example 2 Synthesis of Compound 10

[0053]

[0054] The synthesis method refers to the synthesis of compound 1 in Example 1, except that 3-bromobenzo[kl]xanthene is replaced with 8-bromobenzo[kl]xanthene to obtain compound 10.

[0055] The compound represented by Formula 10 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 627.

[0056] Synthesis Example 3 Synthesis of Compound 28

[0057] (1) Synthesis of intermediate M-2

[0058]

[0059] In a 250 ml three-necked flask, under nitrogen protection, 60 ml toluene, 40 ml ethanol, 20 ml water, and then 2.97 g (0.01 mol) 8-bromobenzo[kl]xanthene, 1.56 g (0.01 mol) 4-chlorophenylboric acid, 2.12 g (0.02 mol) sodium carbonate, and 0.115 g (0.0001 mol) tetrakistriphenylphosphine palladium were added, and the temperature was slowly raised to reflux for reaction for 8 hours, and the temperature was lowered, and water was added to separate the organic layer, and the organic layer was washed with water and dried over magnesium sulfate. After the magnesium sulfate was removed by filtration, the solvent was removed under reduced pressure, and the obtained solid was separated by column chromatography and eluted with petroleum ether to obtain 2.9 g of the compound shown in M-2.

[0060] The compound shown in M-2 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 328.

[0061] (2) Synthesis of the compound represented by formula 28

[0062]

[0063] The synthesis method refers to the synthesis of compound 1 in Example 1, except that 3-bromobenzo[kl]xanthene is replaced by the compound shown in M-2 and the reflux time is changed from 6 hours to 24 hours to obtain compound 28.

[0064] The compound represented by Formula 28 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 703.

[0065] Synthesis Example 4 Synthesis of Compound 49

[0066] (1) Synthesis of intermediate M-3

[0067]

[0068] In a 250 ml three-necked flask, add 50 ml DMF and 2.97 g (0.01 mol) 8-bromobenzo[kl]xanthene, control the temperature at 20-25°C, add 2.25 g (0.01 mol) N-iodosuccinimide (NIS) in batches under stirring, then control the temperature at 20-25°C to react for 2 hours, then raise the temperature to 40-45°C to react for 1 hour, then raise the temperature to 60°C to react for 1 hour, cool down, add water and dichloromethane for separation, wash the organic layer with water, separate it by silica gel column chromatography, and elute with petroleum ether to obtain 1.8 g of the compound shown in M-3.

[0069] The compound represented by formula M-3 was detected by mass spectrometry. The two largest peaks were 422 and 424. The molecular formula of the product was determined to be: C 16 H 8 BrIO.

[0070] The compound represented by formula M-3 was subjected to NMR detection, and the data analysis was as follows: 1H-NMR (Bruker Company, Switzerland, AvanceⅡ400MHz NMR spectrometer, CDCl3), δ8.51 (m, 1H), δ7.88 (m, 1H), δ7.82 (m, 2H), δ7.68 (m, 1H), δ7.62 (d, 1H), δ7.44 (d, 1H), δ7.10 (m, 1H).

[0071] (2) Synthesis of intermediate M-4

[0072]

[0073] In a 250 ml three-necked flask, under nitrogen protection, add 60 ml toluene, 40 ml ethanol, 20 ml water, and then add 4.23 g (0.01 mol) of the compound shown in M-3, 1.22 g (0.01 mol) of phenylboric acid, 2.12 g (0.02 mol) of sodium carbonate, and 0.115 g (0.0001 mol) of tetrakistriphenylphosphine palladium. Slowly raise the temperature to 60 ° C and react for 8 hours. Cool down and add water to separate. After washing the organic layer with water, add magnesium sulfate and a small amount of 200-300 mesh silica gel to dry. After filtering to remove magnesium sulfate and silica gel, remove the solvent under reduced pressure. The obtained solid is recrystallized twice with a mixed solvent of chlorobenzene and methanol to obtain 3.1 g of the compound shown in M-4.

[0074] The compound M-4 was detected by mass spectrometry. The two largest peaks were 372 and 374. The molecular formula of the product was determined to be: C 22 H 13 BrO.

[0075] (3) Synthesis of intermediate M-5

[0076]

[0077] In a 250 ml three-necked flask, under nitrogen protection, 60 ml toluene, 40 ml ethanol, 20 ml water, 3.23 g (0.01 mol) 5-bromo-7,7-dimethyl-7H-benzo[c]fluorene, 1.56 g (0.01 mol) 4-chlorophenylboronic acid, 2.12 g (0.02 mol) sodium carbonate, 0.115 g (0.0001 mol) tetrakistriphenylphosphine palladium were added, and the temperature was slowly raised to reflux for reaction for 8 hours, the temperature was lowered, water was added to separate, the organic layer was washed with water, dried over magnesium sulfate, the magnesium sulfate was filtered off, and the solvent was removed under reduced pressure. The obtained solid was separated by column chromatography and eluted with petroleum ether to obtain 3.0 g of the compound shown in M-5.

[0078] The compound shown in M-5 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be: 354.

[0079] (4) Synthesis of intermediate M-6

[0080]

[0081] In a 250 ml three-necked flask, under nitrogen protection, add 100 ml of dry toluene, 1.69 g (0.01 mol) of 4-aminobiphenyl, 3.55 g (0.01 mol) of the compound shown in M-5, 0.0575 g (0.0001 mol) of Pd(dba)2 (bis(dibenzylideneacetonepalladium), 0.4 g (0.0002 mol) of a toluene solution containing 10% tri-tert-butylphosphine, and 1.44 g (0.015 mol) of sodium tert-butoxide. Heat to reflux for 24 hours, cool, add water to separate, wash the organic layer with water until neutral, dry with magnesium sulfate, filter to remove the magnesium sulfate, concentrate to dryness, and recrystallize with a mixed solvent of toluene and ethanol to obtain 3.9 g of the compound shown in M-6.

[0082] The compound shown in M-6 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be: 487.

[0083] (5) Synthesis of Compound 49

[0084]

[0085] Referring to the synthesis of compound 1 in Example 1, compound 49 was obtained by replacing 3-bromobenzo[kl]oxanthene with the compound shown in M-4 and replacing the compound shown in M-1 with the compound shown in M-6.

[0086] The compound represented by Formula 49 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 779.

[0087] The compound represented by formula 49 was subjected to NMR detection, and the data analysis was as follows: 1H-NMR (Bruker Company, Switzerland, AvanceⅡ400MHz NMR spectrometer, CDCl3), δ8.91~8.86 (m, 2H), δ8.51 (m, 1H), δ8.23 (m, 1H), δ7.93 (m, 1H), δ7.88 (m, 1H), δ7.83 (m, 1H), δ7.74 (m, 2H), δ7.69 (s, 1H), δ7.65 (m, 1H), δ7.60 (m, 1H), δ7.58~7.32 (m, 18H), δ7.29~7.23 (m, 3H), δ7.19~7.13 (m, 2H), δ1.76 (s, 6H).

[0088] Synthesis Example 5 Synthesis of Compound 52

[0089] (1) Synthesis of intermediate M-7

[0090]

[0091] In a 250 ml three-necked flask, under nitrogen protection, add 50 ml of DMF, 4.23 g (0.01 mol) of the compound represented by formula M-3, 0.1 g of cuprous iodide, and 1.08 g (0.02 mol) of sodium methoxide, heat to reflux for 24 hours, cool to room temperature, add water and dichloromethane for separation, wash the organic layer with water until neutral, dry with magnesium sulfate, filter out magnesium sulfate, concentrate the organic layer to dryness, separate by silica gel column chromatography, and elute with petroleum ether: ethyl acetate = 10: 0.5 (volume ratio) to obtain 2.2 g of the compound represented by M-7.

[0092] The compound M-7 was detected by mass spectrometry. The two largest peaks were 326 and 328. The molecular formula of the product was determined to be: C 17 H 11 B O 2 .

[0093] (2) Synthesis of Compound 52

[0094]

[0095] Referring to the synthesis of compound 1 in Example 1, compound 52 was obtained by replacing 3-bromobenzo[kl]oxanthene with the compound shown in M-7 and replacing the compound shown in M-1 with the compound shown in M-6.

[0096] The compound represented by Formula 52 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 733.

[0097] Synthesis Example 6 Synthesis of Compound 53

[0098] (1) Synthesis of intermediate M-8

[0099]

[0100] In a 250 ml three-necked flask, under nitrogen protection, add 50 ml DMF, 4.23 g (0.01 mol) of the compound represented by formula M-3, 0.1 g of cuprous iodide, and 1.16 g (0.02 mol) of KF, heat to reflux for 24 hours, cool to room temperature, add water and dichloromethane for separation, wash the organic layer with water until neutral, dry with magnesium sulfate, filter out the magnesium sulfate, concentrate the organic layer to dryness, separate by silica gel column chromatography, and elute with petroleum ether to obtain 1.6 g of the compound represented by M-8.

[0101] The compound M-8 was detected by mass spectrometry. The two largest peaks were 314 and 316. The molecular formula of the product was determined to be: C 16 H 8 BrFO.

[0102] (2) Synthesis of Compound 53

[0103]

[0104] Referring to the synthesis of compound 1 in Example 1, compound 53 was obtained by replacing 3-bromobenzo[kl]oxanthene with the compound shown in M-8 and replacing the compound shown in M-1 with the compound shown in M-6.

[0105] The compound represented by Formula 53 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 721.

[0106] Synthesis Example 7 Synthesis of Compound 54

[0107] (1) Synthesis of intermediate M-9

[0108]

[0109] In a 250 ml three-necked flask, under nitrogen protection, add 50 ml DMF, 4.23 g (0.01 mol) of the compound represented by formula M-3, 0.1 g of cuprous iodide, and 1.79 g (0.02 mol) of CuCN, heat to reflux for 24 hours, cool to room temperature, add water and dichloromethane for separation, wash the organic layer with water until neutral, dry with magnesium sulfate, filter out the magnesium sulfate, concentrate the organic layer to dryness, separate by silica gel column chromatography, and elute with petroleum ether to obtain 1.9 g of the compound represented by M-9.

[0110] The compound M-9 was detected by mass spectrometry. The two largest peaks were 321 and 323. The molecular formula of the product was determined to be: C 17 H 8 BrNO.

[0111] (2) Synthesis of Compound 54

[0112]

[0113] Referring to the synthesis of compound 1 in Example 1, compound 54 was obtained by replacing 3-bromobenzo[kl]xanthene with the compound shown in M-9 and replacing the compound shown in M-1 with the compound shown in M-6.

[0114] The compound represented by Formula 54 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 728.

[0115] Synthesis Example 8 Synthesis of Compound 77

[0116] (1) Synthesis of intermediate M-10

[0117]

[0118] In a 250 ml three-necked flask, under nitrogen protection, add 30 ml of DMF, 2.97 g (0.01 mol) of 8-bromobenzo[kl]xanthene, 0.5 g of cuprous iodide, and 1.16 g (0.02 mol) of KF, heat to reflux for 24 hours, cool to room temperature, add water and dichloromethane for separation, wash the organic layer with water until neutral, dry with magnesium sulfate, filter out the magnesium sulfate, concentrate the organic layer to dryness, separate by silica gel column chromatography, and elute with petroleum ether to obtain 0.9 g of the compound shown in M-10.

[0119] The compound shown by M-10 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be: 236.

[0120] (2) Synthesis of intermediate M-11

[0121]

[0122] To a 250 ml three-necked flask, add 80 ml of DMF and 2.36 g (0.01 mol) of 8-fluorobenzo[kl]xanthene shown in M-10. Control the temperature at 20-25°C. Add 1.78 g (0.01 mol) of N-bromosuccinimide (NBS) in batches while stirring. Then control the temperature at 20-25°C to react for 6 hours. Add water and dichloromethane for separation. Wash the organic layer with water, separate it by silica gel column chromatography, and elute with petroleum ether to obtain 1.6 g of the compound shown in M-11.

[0123] The compound represented by formula M-11 was detected by mass spectrometry. The two largest peaks were 314 and 316. The molecular formula of the product was determined to be: C 16 H 8 BrFO.

[0124] The compound represented by formula M-11 was subjected to NMR detection, and the data analysis is as follows: 1H-NMR (Bruker Company, Switzerland, AvanceⅡ400MHz NMR spectrometer, CDCl3), δ8.49 (m, 1H), δ7.71 (m, 2H), δ7.68 (m, 1H), δ7.65 (m, 1H), δ7.46 (d, 1H), δ7.24 (m, 1H), δ7.20 (m, 1H).

[0125] (3) Synthesis of Compound 77

[0126]

[0127] Referring to the synthesis of compound 1 in Example 1, compound 77 was obtained by replacing 3-bromobenzo[kl]oxanthene with the compound represented by M-11 and replacing the compound represented by M-1 with the compound represented by M-6.

[0128] The compound shown in 77 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be: 721.

[0129] Synthesis Example 9 Synthesis of Compound 82

[0130]

[0131] Compound 82 was obtained by referring to the synthesis of compound 1 in Example 1 except that 3-bromobenzo[kl]xanthene was replaced with 3-bromobenzo[kl]thioanthene.

[0132] The compound shown in 82 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 643.

[0133] Synthesis of comparative compounds

[0134] Synthesis of comparative compound H-1:

[0135]

[0136] Referring to the synthesis of compound 1 in Example 1, the 3-bromobenzo[kl]xanthene was replaced with 8-bromobenzo[kl]xanthene, and the compound represented by M-1 was replaced with N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine to obtain compound H-1.

[0137] The compound shown in H-1 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 577.

[0138] Synthesis of comparative compound H-2

[0139]

[0140] The synthesis of compound 1 in Example 1 was performed by referring to the method except that the compound M-1 was replaced by N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine to obtain compound H-2.

[0141] The compound shown in H-2 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 577.

[0142] Materials used in device examples:

[0143]

[0144]

[0145] Device Example 1

[0146] The examples use the compounds of the present application as hole transport materials in organic electroluminescent devices, and the comparative examples use H-1 to H-4 as hole transport materials in organic electroluminescent devices.

[0147] The structure of the organic electroluminescent device is: ITO / HIL02 (100nm) / hole transport material (40nm) / EM1 (30nm) / TPBI (30nm) / LiF (0.5nm) / Al (150nm).

[0148] The preparation process of organic electroluminescent device is as follows:

[0149] The glass substrate coated with an ITO transparent conductive layer (as an anode) is ultrasonically treated in a cleaning agent, then rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol, baked in a clean environment until the water is completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam to improve the properties of the surface and enhance the binding ability with the hole injection layer;

[0150] The glass substrate was placed in a vacuum chamber and evacuated to 1×10 -5 ~9×10 -3 Pa, vacuum evaporate HIL02 on the anode as a hole injection layer, the evaporation rate is 0.1nm / s, and the evaporation film thickness is 100nm;

[0151] The compound of the present application and the comparative material are vacuum-deposited on the hole injection layer as a hole transport layer, respectively, with a deposition rate of 0.1 nm / s and a deposition film thickness of 40 nm;

[0152] Vacuum evaporate EM1 on the hole transport layer as the organic light-emitting layer of the device, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 30 nm;

[0153] Vacuum evaporation of TPBI on the organic light-emitting layer as the electron transport layer of the organic electroluminescent device; the evaporation rate is 0.1nm / s, and the total evaporation film thickness is 30nm;

[0154] 0.5 nm of LiF and 150 nm of Al were vacuum-deposited on the electron transport layer to serve as an electron injection layer and a cathode.

[0155] The brightness, driving voltage and current efficiency of the prepared organic electroluminescent device were measured.

[0156] The performance of the organic electroluminescent device is shown in Table 1. The test was conducted using the OLED-1000 multi-channel accelerated aging life and light color performance analysis system produced by Hangzhou Yuanfang.

[0157] Table 1

[0158] Hole transport materials <![CDATA[Required brightness cd / m 2 > Drive voltage V Current efficiency cd / A HT-1 1000 5.62 1.58 HT-2 1000 5.88 1.62 HT-3 1000 5.39 1.69 HT-4 1000 5.61 1.51 1 1000 5.26 1.78 82 1000 5.33 1.86 3 1000 5.38 2.01 4 1000 5.22 1.98 6 1000 5.12 2.31 13 1000 5.27 2.19 17 1000 5.01 2.11 25 1000 5.28 2.01 28 1000 5.18 1.96 35 1000 5.16 2.12 46 1000 5.11 1.89 49 1000 4.52 1.96 53 1000 4.62 2.01 54 1000 4.37 2.03 56 1000 4.51 1.98 59 1000 4.58 1.82 66 1000 4.33 1.98 71 1000 4.62 2.21 77 1000 4.53 2.19

[0159] From the data in Table 1, it can be seen that the organic electroluminescent device using the compounds of the present application as hole transport materials can improve the luminous efficiency and reduce the driving voltage. The current efficiency of the organic electroluminescent device prepared using the compounds of the present application can reach more than 1.8cd / A. In particular, the devices corresponding to compounds 49 to 77 have a more excellent effect, and the driving voltage of the devices corresponding to compounds 49 to 77 can be reduced to below 4.65V.

[0160] Device Example 2

[0161] The examples use the compounds of the present application as CPL materials in organic electroluminescent devices, and the comparative examples use H-1 to H-4 as CPL materials in organic electroluminescent devices.

[0162] The above-numbered embodiments and comparative examples respectively provide an organic electroluminescent device having the structure of ITO / HIL02 (100 nm) / NPB (40 nm) / EM1 (30 nm) / TPBI (30 nm) / LiF (0.5 nm) / Mg:Ag (2:8) (15 nm) / CPL (70 nm).

[0163] The preparation process of organic electroluminescent device is as follows:

[0164] The glass substrate coated with an ITO transparent conductive layer (as an anode) is ultrasonically treated in a cleaning agent, then rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol, baked in a clean environment until the water is completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam to improve the properties of the surface and enhance the binding ability with the hole injection layer;

[0165] The glass substrate was placed in a vacuum chamber and evacuated to 1×10 -5 ~9×10 -3 Pa, vacuum evaporate HIL02 on the anode as a hole injection layer, the evaporation rate is 0.1nm / s, and the evaporation film thickness is 100nm;

[0166] NPB was vacuum evaporated on the hole injection layer as a hole transport layer, with an evaporation rate of 0.1 nm / s and an evaporation film thickness of 40 nm;

[0167] Vacuum evaporate EM1 on the hole transport layer as the organic light-emitting layer of the device, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 30 nm;

[0168] Vacuum evaporation of TPBI on the organic light-emitting layer as the electron transport layer of the organic electroluminescent device; the evaporation rate is 0.1nm / s, and the total evaporation film thickness is 30nm;

[0169] 0.5 nm LiF was vacuum evaporated on the electron transport layer as an electron injection layer;

[0170] Mg / Ag was vacuum-deposited on the electron injection layer as the cathode, where the ratio of Mg:Ag was 2:8 and the thickness of the evaporated film was 15 nm;

[0171] The CPL material is vacuum evaporated on the cathode, and the evaporated film thickness is 70nm.

[0172] The organic electroluminescent devices of the embodiment and the comparative example are all prepared by the above method, and the only difference is the selection of CPL materials, as shown in Table 2 for details.

[0173] Performance Test:

[0174] The brightness and current efficiency of the prepared organic electroluminescent device were measured using the OLED-1000 multi-channel accelerated aging life and light color performance analysis system produced by Hangzhou Yuanfang. The test results are shown in Table 2.

[0175] Table 2

[0176] CPL Materials <![CDATA[Required brightness cd / m 2 > Current efficiency cd / A H-1 1000 2.01 H-2 1000 2.02 H-3 1000 1.98 H-4 1000 1.99 1 1000 2.56 82 1000 2.67 3 1000 2.68 4 1000 2.32 6 1000 2.65 13 1000 2.58 35 1000 2.59 44 1000 2.69 47 1000 2.77

[0177] From the data in Table 2 above, it can be seen that the use of the compounds provided in this application as CPL materials of organic electroluminescent devices can improve the luminous efficiency. Specifically, the current efficiency of organic electroluminescent devices prepared using the compounds of this application can reach above 2.3 cd / A, and some can reach above 2.6 cd / A.

[0178] Obviously, those skilled in the art can make various changes and modifications to the embodiments of the present application without departing from the spirit and scope of the present application. Thus, if these modifications and variations of the present application fall within the scope of the claims of the present application and their equivalents, the present application is also intended to include these modifications and variations.

Claims

1. A compound, It is characterized in that The compound is selected from one of the following structural formulas:

2. An organic electroluminescent device, It is characterized in that The organic electroluminescent device comprises the compound according to claim 1.

3. A display device, It is characterized in that Comprising the organic electroluminescent device as claimed in claim 2.

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