Compound, organic electroluminescent device, display device and intermediate compound

Abstract

The invention relates to the field of electroluminescence, and discloses a compound, an organic electroluminescent device, a display device and an intermediate compound. The structural formula of the compound is as shown in formula (I). The organic electroluminescent device using the material of the compound has low driving voltage and high current efficiency.

Description

[0001] This application is a divisional application of the patent application with application number 202110207655.6 (the application date of the original application is February 24, 2021, and the name of the invention is A compound and an organic electroluminescent device and a display device). Technical Field

[0002] The present application relates to the field of electroluminescence, and in particular to a compound, an organic electroluminescent device, a display device and an intermediate compound. Background Art

[0003] Currently, organic electroluminescent (OLED) display technology has been applied in fields such as smartphones and tablets, and is expected to expand into larger display applications such as televisions. Over the past 30 years, researchers have developed a variety of high-performance OLED materials. Through diverse device structural designs and optimization of performance factors such as device lifespan and efficiency, OLED's commercialization has been accelerated, leading to its widespread application in the display and lighting fields.

[0004] 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 because the mode loss of the substrate, the loss of surface plasmons and the waveguide effect confine 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 (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 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.

[0005] In addition, the choice 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. Currently, we are still exploring functional layer materials with higher performance.

[0006] Therefore, in order to meet people's higher requirements for OLED devices, the field urgently needs to develop more types of OLED materials with higher performance. Summary of the Invention

[0007] The present application discloses a carbazole compound, an organic electroluminescent device, a display device and an intermediate compound. The organic electroluminescent device using the compound of the present application has a lower driving voltage and a higher current efficiency.

[0008] To achieve the above objectives, this application provides the following technical solutions:

[0009] A compound, the structural formula of the compound is shown in formula (I),

[0010]

[0011] Wherein, m, n, p are selected from 0 or 1;

[0012] 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;

[0013] 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;

[0014] Ar2 is selected from an aromatic group containing 6 to 40 carbon atoms or formula (II), wherein the hydrogen in the aromatic group containing 6 to 40 carbon atoms may be replaced by R;

[0015] 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;

[0016] R and R1~R 10 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.

[0017] Furthermore, 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.

[0018] 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.

[0019] Furthermore, the structure of the compound is one of the following structures:

[0020]

[0021] Furthermore, the structure of the compound is one of the following structures:

[0022]

[0023] Furthermore, R1 and R 10 Each is independently selected from one of F, CN, methoxy, phenyl or biphenyl.

[0024] Furthermore, the compound is one of the following structures:

[0025]

[0026]

[0027]

[0028]

[0029]

[0030] An organic electroluminescent device, comprising the compound described in the present application.

[0031] A display device includes the organic electroluminescent device provided in the present application.

[0032] Compared with the prior art, the present invention has the following beneficial effects:

[0033] The compound represented by formula (I) of the present application is a novel compound that can be used in organic electroluminescent devices as HTL, EBL, and host materials. Furthermore, OLED devices prepared using the compound represented by formula (I) of the present application have low driving voltage and high luminous efficiency. DETAILED DESCRIPTION

[0034] 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 embodiments described are only part of the embodiments of the present application, not all of the embodiments. Based on the embodiments of the present application, all other embodiments obtained by ordinary technicians in this field without making creative efforts are within the scope of protection of this application.

[0035] It should be noted that, unless otherwise specified, all embodiments and preferred implementation methods described herein can be combined to form new technical solutions. Unless otherwise specified, all technical features and preferred features described herein can be combined to form new technical solutions. Unless otherwise specified, percentages (%) or parts refer to percentages or parts by weight relative to the composition. Unless otherwise specified, the components or preferred components described herein can be combined to form new technical solutions. Unless otherwise specified, the numerical range "a-b" is an abbreviation for any combination of real numbers between a and b, where a and b are both real numbers. For example, the numerical range "6-22" indicates that all real numbers between "6-22" are listed herein, and "6-22" is merely an abbreviation for these numerical combinations. "Range" disclosed herein in the form of lower limits and upper limits can refer to one or more lower limits and one or more upper limits, respectively. Unless otherwise specified, the reactions or steps described herein can be performed sequentially or non-sequentially. Preferably, the reaction methods described herein are performed sequentially.

[0036] Unless otherwise indicated, 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 this application.

[0037] The present application provides a compound, the structural formula of which is shown in formula (I):

[0038]

[0039] Wherein, m, n, p are selected from 0 or 1;

[0040] 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;

[0041] 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;

[0042] Ar2 is selected from an aromatic group containing 6 to 40 carbon atoms or formula (II), wherein the hydrogen in the aromatic group containing 6 to 40 carbon atoms may be replaced by R;

[0043] 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;

[0044] R and R1~R10 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.

[0045] Specifically, as an exemplary illustration, the compounds defined in the present application may include any one of those in Table 1.

[0046] Table 1

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057] Among them, in each compound listed in Table 1, each fragment is connected by an Sp2 hybridized carbon atom, and any Sp2 hybridized carbon atom can participate in the connection. If the fragment is composed of two or more aromatic rings, these two or more aromatic rings can also be connected arbitrarily. For example, the following is an example: Compound 1-2 in Table 1 includes but is not limited to the following structure:

[0058]

[0059]

[0060] Synthesis Example 1 Synthesis of Compound B-1 (A-37)

[0061] The synthetic route is as follows:

[0062]

[0063] To a 500 ml three-necked flask under nitrogen protection, 250 ml of dry toluene, 4.84 g (0.01 mol) of the compound represented by M-1, 2.97 g (0.01 mol) of 3-bromobenzo[kl]xanthene, 0.0575 g (0.0001 mol) of Pd(dba)2 (bisdibenzylideneacetone palladium), 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 were added. The mixture was heated to reflux for 6 hours, cooled, and separated by adding water. The organic layer was washed with water until neutral, dried over magnesium sulfate, filtered to remove the magnesium sulfate, and concentrated to dryness. The mixture was separated by silica gel column chromatography and eluted with petroleum ether:ethyl acetate = 10:0.5 (volume ratio) to obtain 5.8 g of the compound represented by formula B-1.

[0064] The compound represented by formula B-1 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 699.

[0065] The compound represented by formula B-1 was subjected to nuclear magnetic resonance detection, and the data analysis is as follows: 1H-NMR (Bruker Company, Switzerland, AvanceⅡ400MHz nuclear magnetic resonance spectrometer, CDCl3), δ8.06 (m, 1H), δ7.96 (m, 1H), δ7.93~7.84 (m, 4H), δ7.73 (m, 2H), δ7.69 (m, 2H), δ7.62 (d, 1H), δ7.60~7.44 (m, 6H), δ7.43~7.20 (m, 13H), δ7.19~7.13 (m, 2H), δ6.39 (m, 1H).

[0066] Synthesis Example 2 Synthesis of Compound B-2

[0067] The synthetic route is as follows:

[0068]

[0069] The synthesis method refers to the synthesis of compound B-1 in Example 1, replacing the compound represented by M-1 with the compound represented by M-2, and replacing 3-bromobenzo[kl]xanthene with 3-(4-bromophenyl)benzo[kl]xanthene to obtain compound B-2.

[0070] The compound shown in B-2 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 815.

[0071] Synthesis Example 3 Synthesis of Compound B-3

[0072] The synthetic route is as follows:

[0073]

[0074] The synthesis method refers to the synthesis of compound B-1 in Example 1, except that the compound represented by M-1 is replaced by the compound represented by M-21 to obtain compound B-3.

[0075] The compound shown in B-3 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 775.

[0076] Synthesis Example 4 Synthesis of Compound B-4

[0077]

[0078] The synthesis method refers to the synthesis of compound B-1 in Example 1, except that the compound represented by M-1 is replaced by the compound represented by M-21, and the 3-bromobenzo[kl]xanthene is replaced by 3-(4-bromophenyl)benzo[kl]xanthene to obtain compound B-4.

[0079] The compound shown in B-4 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be: 851.

[0080] Synthesis Example 5 Synthesis of Compound A-11

[0081] (1) Synthesis of intermediate M-10

[0082]

[0083] To a 250 ml three-necked flask under nitrogen atmosphere were added 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. The mixture was heated to reflux for 24 hours, cooled to room temperature, and separated by addition of water and dichloromethane. The organic layer was washed with water until neutral, dried over magnesium sulfate, and the magnesium sulfate was filtered off. The organic layer was concentrated to dryness and separated by silica gel column chromatography and eluted with petroleum ether to obtain 0.9 g of compound M-10.

[0084] The compound represented by M-10 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be: 236.

[0085] (2) Synthesis of intermediate M-11

[0086]

[0087] 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 compound shown in M-11.

[0088] 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.

[0089] The compound represented by formula M-11 was subjected to nuclear magnetic resonance detection, and the data analysis is as follows: 1H-NMR (Bruker Company, Switzerland, AvanceⅡ400MHz nuclear magnetic resonance 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).

[0090] (3) Synthesis of Compound A-11

[0091]

[0092] The synthesis method refers to the synthesis of compound B-1 in Example 1, replacing the compound represented by M-1 with the compound represented by M-2, and replacing 3-bromobenzo[kl]xanthene with the compound represented by M-11 to obtain compound A-11.

[0093] The compound represented by A-11 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 757.

[0094] Synthesis Example 6 Synthesis of Compound A-25

[0095] (1) Synthesis of intermediate M-3

[0096]

[0097] To a 250 ml three-necked flask, add 50 ml of DMF and 2.97 g (0.01 mol) of 8-bromobenzo[kl]xanthene. Control the temperature at 20-25°C. Under stirring, add 2.25 g (0.01 mol) of N-iodosuccinimide (NIS) in batches. 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, 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 compound M-3.

[0098] 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.

[0099] The compound represented by formula M-3 was subjected to nuclear magnetic resonance detection, and the data analysis is as follows: 1H-NMR (Bruker Company, Switzerland, AvanceⅡ400MHz nuclear magnetic resonance 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).

[0100] (2) Synthesis of intermediate M-4

[0101]

[0102] To a 250 ml three-necked flask, under nitrogen protection, were added 60 ml of toluene, 40 ml of ethanol, and 20 ml of water, followed by 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. The temperature was slowly raised to 60°C for reaction for 8 hours, the temperature was lowered, water was added to separate the mixture, the organic layer was washed with water, magnesium sulfate and a small amount of 200-300 mesh silica gel were added for drying, the magnesium sulfate and silica gel were filtered out, and the solvent was removed under reduced pressure. The obtained solid was recrystallized twice from a mixed solvent of chlorobenzene and methanol to obtain 3.1 g of the compound shown in M-4.

[0103] 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.

[0104] (3) Synthesis of Compound A-25

[0105]

[0106] The synthesis method refers to the synthesis of compound B-1 in Example 1, and the 3-bromobenzo[kl]xanthene is replaced with the compound shown in M-4 to obtain compound A-25.

[0107] The compound represented by A-25 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 775.

[0108] Synthesis Example 7 Synthesis of Compound A-28

[0109] (1) Synthesis of intermediate M-8

[0110]

[0111] To a 250 ml three-necked flask, under nitrogen protection, were added 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 1.16 g (0.02 mol) of KF. The mixture was heated to reflux for 24 hours, cooled to room temperature, and separated by adding water and dichloromethane. The organic layer was washed with water until neutral, dried over magnesium sulfate, and the magnesium sulfate was filtered off. The organic layer was concentrated to dryness, separated by silica gel column chromatography, and eluted with petroleum ether to obtain 1.6 g of the compound represented by M-8.

[0112] The compound shown in 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.

[0113] (2) Synthesis of Compound A-28

[0114]

[0115] The synthesis method refers to the synthesis of compound B-1 in Example 1, and the 3-bromobenzo[kl]xanthene therein is replaced with the compound shown in M-8 to obtain compound A-28.

[0116] The compound represented by A-28 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 717.

[0117] Synthesis Example 8 Synthesis of Compound A-29

[0118] (1) Synthesis of intermediate M-9

[0119]

[0120] To a 250 ml three-necked flask, under nitrogen protection, were added 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 1.79 g (0.02 mol) of CuCN. The mixture was heated to reflux for 24 hours, cooled to room temperature, and separated by adding water and dichloromethane. The organic layer was washed with water until neutral, dried over magnesium sulfate, and the magnesium sulfate was filtered off. The organic layer was concentrated to dryness, separated by silica gel column chromatography, and eluted with petroleum ether to obtain 1.9 g of the compound represented by M-9.

[0121] The compound shown in 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.

[0122] (2) Synthesis of Compound A-29

[0123]

[0124] The synthesis method refers to the synthesis of compound B-1 in Example 1, except that 3-bromobenzo[kl]xanthene is replaced with the compound shown in M-9 to obtain compound A-29.

[0125] The compound represented by A-29 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 724.

[0126] Synthesis Example 9 Synthesis of Compound BS-1

[0127]

[0128] Referring to the synthesis of compound B-1 in Example 1, the 3-bromobenzo[kl]xanthene was replaced with 3-bromobenzo[kl]thioanthene to obtain compound BS-1.

[0129] The compound represented by BS-1 was detected by mass spectrometry, and the m / z of the molecule was determined to be 715.

[0130] Device Example:

[0131] Synthesis of HT-4:

[0132]

[0133] Referring to the synthesis of compound 1 in Example 1, except that 3-bromobenzo[kl]xanthene was replaced with 5-naphtho[2,1-b]benzofuran, compound HT-4 was obtained.

[0134] The compound represented by HT-4 was detected by mass spectrometry, and the m / z of the molecule was determined to be 699.

[0135] It should be noted that the preparation methods of the above compounds are only illustrative, and other compounds within the scope of this application can be prepared by referring to the preparation methods of the above-mentioned example compounds.

[0136] The specific structures of several materials used in the device embodiments of this application are as follows:

[0137]

[0138]

[0139] Device Example 1

[0140] The device of this embodiment uses the compound of the present application as the hole transport material in the organic electroluminescent device, and the comparative example uses HT-1 to H-4 as the hole transport material in the organic electroluminescent device.

[0141] The structure of the organic electroluminescent device is: ITO / HIL02 (100 nm) / hole transport material (40 nm) / EM1 (35 nm) / TPBI (30 nm) / LiF (0.5 nm) / Al (150 nm).

[0142] The preparation process of organic electroluminescent devices is as follows:

[0143] A glass substrate coated with an ITO transparent conductive layer (as an anode) was ultrasonically treated in a cleaning agent, then rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol, and baked in a clean environment until the water was completely removed. The substrate was then cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam to improve the surface properties and enhance its binding ability with the hole injection layer.

[0144] 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;

[0145] The compound of the present application and the comparative material were 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;

[0146] EM1 was vacuum evaporated on the hole transport layer as the organic light-emitting layer of the device at a deposition rate of 0.1 nm / s and a total film thickness of 35 nm.

[0147] TPBI was vacuum-deposited on the organic light-emitting layer as an electron transport layer of the organic electroluminescent device at a deposition rate of 0.1 nm / s and a total deposition thickness of 30 nm.

[0148] 0.5 nm of LiF and 150 nm of Al were vacuum-deposited on the electron transport layer to serve as the electron injection layer and cathode.

[0149] The brightness, driving voltage and current efficiency of the prepared organic electroluminescent devices were measured.

[0150] The performance of the organic electroluminescent devices is shown in Table 2. The tests were conducted using the OLED-1000 multi-channel accelerated aging lifespan and light color performance analysis system produced by Hangzhou Yuanfang.

[0151] Table 2

[0152] hole transport materials <![CDATA[要求亮度cd / m 2 ]]> Drive voltage V Current efficiency cd / A HT-1 1000 6.02 1.26 HT-2 1000 6.11 1.33 HT-3 1000 6.13 1.31 HT-4 1000 6.66 1.29 B-1 1000 5.62 1.61 BS-1 1000 5.55 1.65 B-2 1000 5.58 1.62 B-3 1000 5.76 1.77 B-4 1000 5.88 1.68 A-11 1000 4.68 1.66 A-25 1000 4.66 1.72 A-28 1000 4.57 1.7 A-29 1000 4.41 1.82 A-32 1000 4.39 1.76 A-34 1000 4.41 1.71

[0153] As can be seen from the data in Table 2, compared to compounds HT-1 to HT-4, the compounds provided by the present application are used as hole transport materials for organic electroluminescent devices, which can improve the current efficiency of the device and reduce the driving voltage. Specifically, compared to the comparative example, the driving voltage of the organic electroluminescent device using the present application's compound as the hole transport material is reduced and the efficiency is increased. The current efficiency of the organic electroluminescent device prepared using the present application's compound can reach more than 1.6cd / A, and the driving voltage can be reduced to less than 6V. In particular, for the devices corresponding to compounds A-11 to A-34, the driving voltage can be reduced to less than 4.7V.

[0154] Device Example 2

[0155] The device of this embodiment uses the compound of the present application as the red light host material in the organic electroluminescent device, and the comparative example uses HT-1 to HT-4 as the red light host material in the organic electroluminescent device.

[0156] The organic electroluminescent device has a structure of: ITO / NPB (20nm) / red light-emitting host material (35nm): Ir(piq)3 [10%] / TPBI (10nm) / Alq3 (15nm) / LiF (0.5nm) / Al (150nm). "Ir(piq)3 [10%]" refers to the doping ratio of the red dye, meaning the weight ratio of the red light-emitting host material to Ir(piq)3 is 100:10.

[0157] 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.

[0158] 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 at a evaporation rate of 0.1 nm / s and a evaporation film thickness of 20 nm;

[0159] The red light host material and dye Ir(piq)3 were vacuum evaporated on the hole transport layer to serve as the light-emitting layer of the organic electroluminescent device. The evaporation rate was 0.1 nm / s and the total film thickness was 35 nm.

[0160] Electron transport layers TPBI and Alq3 were vacuum-deposited on the light-emitting layer at a rate of 0.1 nm / s and a thickness of 10 nm and 15 nm, respectively.

[0161] 0.5nm of LiF and 150nm of Al were vacuum evaporated on the electron transport layer as electron injection layer and cathode.

[0162] All the organic electroluminescent devices were prepared by the above method, the only difference was the selection of red light host material, see Table 3 below for details.

[0163] Performance test:

[0164] The luminance, driving voltage, current efficiency of the prepared organic electroluminescent devices were measured by using OLED-1000 multi-channel accelerated aging life and light color performance analysis system produced by Hangzhou Yuanfang, and the test results are shown in the following table.

[0165] Table 3

[0166] Red light main material <![CDATA[要求亮度cd / m 2 ]]> Drive voltage V Current efficiency cd / A HT-1 1000 5.11 40.22 HT-2 1000 5.30 38.19 HT-3 1000 5.19 41.23 HT-4 1000 5.18 42.33 B-2 1000 4.66 50.76 B-3 1000 4.78 51.88 B-4 1000 4.77 52.33 B-5 1000 4.73 52.65 A-25 1000 3.96 51.56 A-28 1000 4.10 55.41 A-29 1000 4.06 52.22 A-36 1000 4.15 53.18

[0167] From the data in Table 3, compared with compounds HT-1 to HT-4, the compound provided by the present application as a red light host material of an organic electroluminescent device can improve the current efficiency of the device and reduce the driving voltage. Specifically, compared with the comparative examples, the organic electroluminescent device using the compound of the present application as a red light host material has a lower driving voltage and a higher efficiency. The current efficiency of the organic electroluminescent device prepared by using the compound of the present application can reach more than 50 cd / A, and the driving voltage can be reduced to less than 4.8V. Especially for the devices corresponding to compounds A-25 to A-36, the driving voltage can be reduced to less than 4.2V.

[0168] Obviously, those skilled in the art can make various modifications and variations 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 equivalent technologies, the present application also intends to include these modifications and variations.

Claims

1. A compound, characterized in that The structural formula of the compound is shown in formula (I): Wherein, m, n, and p are selected from 0 or 1; A is selected from any one of phenylene, biphenylene, fluorenylene, and 9,9-dimethylfluorenylene; B is selected from phenylene or biphenylene; Q is selected from phenylene; The hydrogen atoms in A, B, and Q can each be replaced by R independently; Ar1 is selected from the group of 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), and X is selected from oxygen or sulfur; Ar2 is selected from any one of phenyl, biphenyl, and 9,9-dimethylfluorenyl, and each hydrogen in Ar2 can be independently replaced by R; Ar3 is selected from the group of formula (III), * represents the connection position of Ar3 and Q or N atom in formula (I); R, R1~R 10 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, a phenyl group or a biphenyl group.

2. The compound according to claim 1, characterized in that The structure of the compound is shown below: Among them, m, n, p, Ar2, Ar3, X, R1~R 10 Has the same definition as claim 1.

3. The compound according to claim 2, characterized in that The structure of the compound is shown below: Among them, m, n, p, Ar2, Ar3, X, R1, R 10 Has the same definition as claim 1.

4. The compound according to claim 3, characterized in that R1 and R 10 Each is independently selected from any one of -F, -CN, methoxy, phenyl or biphenyl.

5. The compound according to claim 1, characterized in that The compound includes one of the following compounds:

6. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises the compound according to any one of claims 1 to 5.

7. A display device, characterized in that: The display device comprises the organic electroluminescent device according to claim 6.

8. An intermediate compound for preparing the compound according to any one of claims 1 to 5, characterized in that: The intermediate compounds include the following compounds:

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