Compounds and organic electroluminescent devices and intermediate compounds

Abstract

The present application relates to the field of electroluminescence, and discloses a compound, an organic electroluminescent device and an intermediate compound. 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, an organic electroluminescent device and an intermediate compound. 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 an intermediate compound. 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, p are selected from 0 or 1;

[0011] A, B, and Q are each 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] Ar1 is selected from formula (II), wherein R1 to 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] Ar2 is selected from one of the structures shown in the following A-1 to A-7,

[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] Ar3 is selected from formula (III), * represents the position where Ar3 is connected to the Q or N atom in formula (I), and the hydrogen in Ar3 may be replaced by one or more R;

[0019] R and R1~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.

[0020] Further, A, B, and Q are 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 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.

[0022] Furthermore, the structure of the compound is:

[0023]

[0024] Furthermore, the structure of the compound is:

[0025]

[0026] Furthermore, R1 and R 10 Each is independently selected from one of F, CN, methoxy, phenyl or biphenyl.

[0027] Furthermore, the compound includes one of the following structures:

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037] Furthermore, the compound is one of structural formulas 97 to 192, wherein the compounds of structural formulas 97 to 192 are obtained by replacing O with S in the compounds of structural formulas 1 to 96, respectively.

[0038] An organic electroluminescent device comprises the compound described in the present application.

[0039] A display device includes the organic electroluminescent device provided in the present application.

[0040] An intermediate compound for preparing the compound of formula (I) of the present application, wherein the structural formula of the intermediate compound is as shown in formula (IV) and formula (V),

[0041]

[0042] Wherein, Y is selected from chlorine or bromine.

[0043] Furthermore, the intermediate compound is selected from one of the following structures:

[0044]

[0045] A method for preparing the compound of formula (I), comprising the following steps:

[0046] Compound A01 With compound A02 The reaction forms formula (IV) The intermediate compounds shown;

[0047] The intermediate compound represented by formula (IV) is reacted with the intermediate compound represented by formula (V) The intermediate compound shown is reacted to form a compound of formula (I); wherein Y is selected from chlorine or bromine.

[0048] Specifically, the specific synthetic route of the compound of formula (I) can be, for example:

[0049]

[0050] wherein Y is selected from chlorine or bromine.

[0051] The technical solution of this application produces the following beneficial effects:

[0052] The compound represented by formula (I) of the present application is a new compound and can be used in organic electroluminescent devices as HTL, EBL, and Host 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

[0053] 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.

[0054] 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.

[0055] 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.

[0056] Synthesis Example 1 Synthesis of Compound 1

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

[0058]

[0059] In a 250 ml three-necked flask, under nitrogen protection, add 120 ml of dry toluene, 3.31 g (0.01 mol) of 2-aminospirobifluorene, 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 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 ethanol to obtain 3.6 g of the compound shown in M-1.

[0060] The compound shown in M-1 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be: 573.

[0061] (2) Synthesis of the compound represented by formula 1

[0062]

[0063] In a 500 ml three-necked flask, under nitrogen protection, add 250 ml of dry toluene, 5.74 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:ethyl acetate=10:0.5 (volume ratio) to obtain 6.2 g of the compound shown in formula 1.

[0064] The compound represented by Formula 1 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 789.

[0065] 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), δ8.85 (m, 1H), δ8.21 (d, 1H), δ8.04 (m, 1H), δ7.96 (m, 1H), δ7.91~7.87 (m, 3H), δ7.86 (d, 1H), δ7.74 (m, 1H), δ7.65~7.49 (m, 9H), δ7.41 (m, 1H), δ7.36~7.31 (m, 2H), δ7.30~7.15 (m, 10H), δ7.09 (d, 1H), δ6.41 (m, 1H), δ1.76 (s, 6H).

[0066] Synthesis Example 2 Synthesis of Compound 13

[0067]

[0068] 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 13.

[0069] The compound represented by Formula 13 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 789.

[0070] Synthesis Example 3 Synthesis of Compound 31

[0071] (1) Synthesis of intermediate M-31-1

[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 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, 0.115 g (0.0001 mol) tetrakistriphenylphosphine palladium, and slowly raise the temperature to reflux for 8 hours, cool, add water to separate, wash the organic layer with water, dry with magnesium sulfate, filter to remove the magnesium sulfate, and remove the solvent under reduced pressure. The obtained solid is separated by column chromatography and eluted with petroleum ether to obtain 2.9 g of the compound shown in M-31-1.

[0074] The compound shown by M-31-1 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be: 328.

[0075] (2) Synthesis of the compound represented by formula 31

[0076]

[0077] 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-31-1, and the reflux time is changed from 6 hours to 32 hours, to obtain compound 31.

[0078] The compound represented by Formula 31 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 865.

[0079] Synthesis Example 4 Synthesis of Compound 55

[0080] (1) Synthesis of intermediate M-3

[0081]

[0082] 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.

[0083] 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 H8BrIO.

[0084] 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).

[0085] (2) Synthesis of intermediate M-4

[0086]

[0087] 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.

[0088] 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.

[0089] (3) Synthesis of intermediate M-5

[0090]

[0091] The synthesis method refers to the synthesis of M-1 in Example 1, except that 9-bromo-7,7-dimethyl-7H-benzo[c]fluorene is replaced with 5-bromo-7,7-dimethyl-7H-benzo[c]fluorene to obtain the compound shown in M-5.

[0092] The compound shown in M-5 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be: 573.

[0093] (4) Synthesis of Compound 55

[0094]

[0095] Referring to the synthesis of compound 1 in Example 1, compound 55 was obtained by replacing 3-bromobenzo[kl]xanthene with the compound shown in M-4 and replacing the compound shown in M-1 with the compound shown in M-5.

[0096] The compound represented by Formula 55 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 865.

[0097] The compound represented by formula 55 was subjected to NMR detection, and the data analysis was as follows: 1H-NMR (Bruker Company, Switzerland, AvanceⅡ400MHz NMR spectrometer, CDCl3), δ8.86 (m, 1H), δ8.50 (m, 1H), δ8.23 (m, 1H), δ8.16 (m, 1H), δ7.95~7.78 (m, 8H), δ7.64~7.40 (m, 9H), δ7.39~7.19 (m, 15H), δ6.88 (s, 1H), δ1.76 (s, 6H).

[0098] Synthesis Example 5 Synthesis of Compound 61

[0099] (1) Synthesis of intermediate M-8

[0100]

[0101] 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.

[0102] 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 H8BrFO.

[0103] (2) Synthesis of Compound 61

[0104]

[0105] Referring to the synthesis of compound 1 in Example 1, compound 61 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-5.

[0106] The compound represented by Formula 61 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 807.

[0107] Synthesis Example 6 Synthesis of Compound 64

[0108] (1) Synthesis of intermediate M-9

[0109]

[0110] 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.

[0111] 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 H8BrNO.

[0112] (2) Synthesis of Compound 64

[0113]

[0114] Referring to the synthesis of compound 1 in Example 1, except that 3-bromobenzo[kl]oxanthene was replaced by the compound shown in M-9, and the compound shown in M-1 was replaced by the compound shown in M-5, compound 64 was obtained.

[0115] The compound represented by Formula 64 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 814.

[0116] Synthesis Example 7 Synthesis of Compound 88

[0117] (1) Synthesis of intermediate M-10

[0118]

[0119] 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.

[0120] The compound shown by M-10 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be: 236.

[0121] (2) Synthesis of intermediate M-11

[0122]

[0123] 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.

[0124] 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 H8BrFO.

[0125] 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).

[0126] (3) Synthesis of Compound 88

[0127]

[0128] Referring to the synthesis of compound 1 in Example 1, compound 88 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-5.

[0129] The compound shown in 88 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be: 807.

[0130] Synthesis Example 8 Synthesis of Compound 97

[0131]

[0132] Compound 97 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.

[0133] The compound 97 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 805.

[0134] Synthesis of comparative compounds

[0135] Synthesis of H-1:

[0136]

[0137] 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'-spirobifluorene]-2-amine to obtain compound H-1.

[0138] The compound shown in H-1 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 699.

[0139] Synthesis of H-2

[0140]

[0141] Referring to the synthesis of compound 1 in Example 1, the compound M-1 was replaced with N-([1,1'-biphenyl-4-yl)-9,9'-spirobifluorene]-2-amine to obtain compound H-2.

[0142] The compound shown in H-2 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 739.

[0143] The specific structures of several materials used in this application are as follows:

[0144]

[0145]

[0146] Device Example 1

[0147] 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-3 as hole transport materials in organic electroluminescent devices.

[0148] The structure of the organic electroluminescent device is: ITO / HIL02 (100nm) / hole transport material (40nm) / EM1 (30nm) / Alq3 (30nm) / LiF (0.5nm) / Al (150nm).

[0149] The preparation process of organic electroluminescent device is as follows:

[0150] 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;

[0151] 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;

[0152] 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;

[0153] 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;

[0154] Vacuum-deposit Alq3 on the organic light-emitting layer as the electron transport layer of the organic electroluminescent device; the evaporation rate is 0.1 nm / s, and the total evaporation film thickness is 30 nm;

[0155] 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.

[0156] The brightness, driving voltage and current efficiency of the prepared organic electroluminescent device were measured.

[0157] 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.

[0158] Table 1

[0159] Hole transport materials <![CDATA[Required luminance cd / m 2 > Drive voltage V Current efficiency cd / A HT-1 1000 6.23 1.13 HT-2 1000 6.15 1.22 HT-3 1000 5.99 1.21 1 1000 5.46 1.56 97 1000 5.53 1.66 4 1000 5.66 1.50 6 1000 5.59 1.38 14 1000 5.62 1.31 20 1000 5.27 1.32 27 1000 5.38 1.29 31 1000 5.67 1.42 43 1000 5.49 1.36 48 1000 5.56 1.51 91 1000 5.55 1.43 94 1000 4.37 1.50 55 1000 4.32 1.45 61 1000 4.39 1.33 64 1000 4.54 1.29 88 1000 4.59 1.38 68 1000 4.49 1.32

[0160] It can be seen from the data in Table 1 that the voltage of the organic electroluminescent device using the compound of the present application as the hole transport material is reduced and the efficiency is increased. Specifically, compared with the comparative example, the current efficiency of the organic electroluminescent device prepared using the compound of the present application can reach 1.29cd / A or more, and the driving voltage can be reduced to below 5.7V. In particular, the devices corresponding to compounds 94, 55, 61, 64, 88, and 68 can reduce the driving voltage to below 4.6V.

[0161] Device Example 2

[0162] The examples use the compounds of the present application as green light host materials in organic electroluminescent devices, and the comparative examples use H-1 to H-3 as green light host materials in organic electroluminescent devices.

[0163] The structure of the organic electroluminescent device is: ITO / NPB (25nm) / green light host material (30nm): Ir(ppy)3[7%] / TPBI (10nm) / Alq3 (20nm) / LiF (0.5nm) / Al (150nm). "Ir(ppy)3[7%]" refers to the doping ratio of the green light dye, that is, the weight ratio of the green light host material to Ir(ppy)3 is 100:7.

[0164] The organic electroluminescent device was prepared as follows: a glass plate coated with an ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone:ethanol mixed solvent, baked in a clean environment to completely remove water, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

[0165] Place the glass substrate with the anode in a vacuum chamber and evacuate to 1×10 -5 ~9×10 -3 Pa, vacuum evaporating a hole transport layer NPB on the above anode layer film, the evaporation rate is 0.1nm / s, and the evaporation film thickness is 25nm;

[0166] Green light host material and dye Ir(ppy)3 are vacuum evaporated on the hole transport layer as the light-emitting layer of the organic electroluminescent device, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 30 nm;

[0167] The electron transport layer TPBI and Alq3 are vacuum-deposited on the light-emitting layer in sequence, with the evaporation rate of 0.1 nm / s and the thickness of the evaporated films being 10 nm and 20 nm respectively;

[0168] 0.5 nm of LiF and 150 nm of Al were vacuum-deposited on the electron transport layer as the electron injection layer and cathode.

[0169] All organic electroluminescent devices are prepared by the above method, and the only difference is the choice of green light host material, as shown in Table 2 below.

[0170] Performance Testing:

[0171] The brightness, driving voltage 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 the following table.

[0172] Table 2

[0173]

[0174]

[0175] From the data in Table 2 above, it can be seen that compared with the comparative compound, the compound provided in the present application as the green light host material of the organic electroluminescent device can improve the luminous efficiency and reduce the driving voltage. The current efficiency of the organic electroluminescent device prepared using the compound of the present application can reach more than 30cd / A, and the driving voltage can be reduced to below 4.7V. In particular, the effect of compound 96 is more excellent, and the driving voltage of the device corresponding to compound 96 can be reduced to below 4.0V.

[0176] 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, characterized in that The compound is selected from one of the following structural formulas:

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

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