A benzanthraoxanthrene compound, an intermediate, an organic electroluminescent device and a display device

Abstract

The application provides a benzanthanthrene-oxanthrene compound, an intermediate, an organic electroluminescent device and a display device. The benzanthanthrene-oxanthrene compound has a structure as shown in formula BHI. The intermediate is used for preparing the benzanthanthrene-oxanthrene compound. The benzanthanthrene-oxanthrene compound provided by the application can be used as a host material of an organic electroluminescent device light-emitting layer, and thus an organic electroluminescent device with a lower driving voltage, a higher current efficiency and a longer service life is obtained.

Description

TECHNICAL FIELD

[0001] The present application belongs to the technical field of organic electroluminescent materials, and particularly relates to a benzanthraoxanthrene compound, an intermediate, an organic electroluminescent device and a display device. BACKGROUND

[0002] Organic electroluminescence (EL) refers to a phenomenon that organic materials directly convert electric energy into light energy under the action of an electric field. An organic electroluminescent device is a self-luminous device using the above principle, which has the characteristics of self-luminescence, bright and bright color, thin thickness, light weight, fast response speed, wide viewing angle, low driving voltage, resistance to harsh natural conditions, and can be made into a flexible panel, and gradually develops into a new generation of flat panel display technology with the most advantages.

[0003] The structure of an organic electroluminescent device (OLED) includes an anode, a cathode, and an organic layer between the two. In order to improve the efficiency and stability of the organic electroluminescent element, the organic material layer includes multiple layers with different materials, such as a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting layer, an electron transport layer (ETL), and an electron injection layer (EIL), an electron blocking layer, etc. The hole injection layer is a layer that facilitates the injection of holes from the anode of the OLED into the hole transport layer. The hole injection layer is generally directly adjacent to the anode, and one or more hole transport layers are directly adjacent to the hole injection layer on the cathode side. The hole transport layer refers to a layer that transports holes. It is generally a layer located between the cathode and the organic layer closest to the anode. The electron blocking layer blocks electrons from the cathode direction, and compared to the hole transport layer, the electron blocking layer has a shallower LUMO, i.e. the absolute value of the electron blocking layer LUMO is less than the absolute value of the hole transport layer LUMO.

[0004] In order to obtain an organic electroluminescent device with excellent performance, research and development of organic materials has attracted widespread attention, therefore, more types of materials with higher performance are urgently needed in the art to meet the higher requirements of people for OLED devices. SUMMARY

[0005] In view of the deficiencies of the prior art, the purpose of the present application is to provide a benzanthraoxanthrene compound, an intermediate, an organic electroluminescent device and a display device. The benzanthraoxanthrene compound provided by the present application can be used as the host material of the light-emitting layer of the organic electroluminescent device, thereby obtaining an organic electroluminescent device with lower driving voltage, higher current efficiency and longer service life.

[0006] To achieve this purpose, the technical scheme adopted by the present application is as follows:

[0007] The present application provides a benzanthraoxanthrene compound, which has a structure as shown in formula BHI:

[0008]

[0009] wherein Ar 101 and Ar 102 each independently is selected from any one or a combination of at least two of substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C12-C20 heteroaryl;

[0010] m, n are each independently selected from 0 or 1, m, n are not simultaneously 0;

[0011] Ar 101 , Ar 102 each independently is selected from any one or a combination of at least two of -D, -F, -CN, C1-C12 alkyl, C1-C6 alkoxy, C2-C8 alkenyl, C6-C20 aryl, C12-C20 heteroaryl;

[0012] The hydrogen atom in the benzotransanthoxanthene compound of formula BHI can be substituted by a deuterium atom.

[0013] In the present application, by designing the structure of the benzotransanthoxanthene compound, the obtained benzotransanthoxanthene compound can be used as the host material of the light-emitting layer of the organic electroluminescent device, and thus the organic electroluminescent device with lower driving voltage, higher current efficiency and longer lifetime can be obtained.

[0014] In the present application, Ar 101 and Ar 102 each independently is selected from any one or a combination of at least two of substituted or unsubstituted C6-C40 (for example, C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.) aryl, substituted or unsubstituted C12-C20 (for example, C12, C15, C18 or C20, etc.) heteroaryl.

[0015] Ar 101 , Ar 102 each independently is selected from any one or a combination of at least two of -D (deuterium atom), -F, -CN, C1-C12 (for example, C1, C2, C4, C6, C10 or C12, etc.) alkyl, C1-C6 (for example, C1, C2, C3, C4, C5 or C6) alkoxy, C6-C20 (for example, C6, C8, C10, C12, C16 or C20, etc.) aryl, C12-C20 (for example, C12, C15, C18 or C20, etc.) heteroaryl.

[0016] The following are preferred technical solutions of the present application, but not as a limitation of the technical solutions provided by the present application, through the following preferred technical solutions, the purpose and beneficial effects of the present application can be better achieved and realized.

[0017] As a preferred technical solution of the present application, the C6-C40 aryl is selected from any one of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthofluorenyl, pyrenyl, perylenyl, spirofluorenyl, triphenylenyl, fluoranthenyl, hydrobenzanthryl, indenofluorenyl, benzindenofluorenyl, dibenzindenofluorenyl, naphthofluorenyl or benzonaphthofluorenyl.

[0018] Preferably, the C12-C20 heteroaryl is selected from any one of dibenzofuranyl, dibenzothiophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, dinaphthofuranyl or dinaphthothiophenyl.

[0019] As a preferred technical solution of the present application, the C1-C12 alkyl is selected from any one of methyl, ethyl, propyl, butyl or adamantyl.

[0020] Preferably, the C1-C6 alkoxy is selected from any one of methoxy, ethoxy, propoxy or butoxy.

[0021] Preferably, the C6-C20 aryl is selected from any one of phenyl, biphenyl, naphthyl, 9,9-dimethylfluorenyl, fluoranthenyl or triphenylenyl.

[0022] As a preferred technical solution of the present application, the Ar 101 is selected from any one of phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, dibenzofuranyl or dibenzothiophenyl;

[0023] The substituted substituent is selected from any one of methyl, ethyl, propyl, tert-butyl, methoxy, ethoxy, propoxy, butoxy, adamantyl, -D, -F, -CN or phenyl.

[0024] Preferably, the Ar 102 is selected from any one of phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzofluorenyl, fluoranthenyl, triphenylenyl, terphenyl, anthryl, phenanthryl, 9,9-diphenylfluorenyl, spirofluorenyl, indenofluorenyl or hydrobenzanthryl;

[0025] The substituted substituent is selected from any one of phenyl, naphthyl, dibenzofuranyl, fluoranthenyl or triphenylenyl.

[0026] As a preferred technical scheme of the present application, the benzanthraoxanthrene compound is selected from any one of the following substituted or unsubstituted compounds:

[0027]

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039] The substitution means that at least one hydrogen atom in the above-mentioned compound is replaced by a deuterium atom.

[0040] Preferably, the benzanthraoxanthrene compound is selected from any one of the following compounds:

[0041]

[0042]

[0043] In a second aspect, the present application provides an intermediate, which is selected from any one of the following compounds:

[0044]

[0045] wherein Ar 101 has the same protective scope as the first aspect;

[0046] Y is selected from -F, -Cl, -Br or -I;

[0047] The intermediate is used for preparing the benzanthraoxanthrene compound as described in the first aspect.

[0048] As a preferred technical solution of the present application, the intermediate is selected from any one of the following compounds:

[0049]

[0050] wherein Ar 101 selected from The dotted line represents a connecting site;

[0051] Y is selected from -F, -Cl, -Br or -I;

[0052] The intermediate is used for preparing the benzanthraoxanthrene compound as described in the first aspect.

[0053] In the present application, the preparation method of the intermediate and the benzanthraoxanthrene compound is as follows:

[0054]

[0055]

[0056] The preparation method of the benzanthraoxanthrene compound further comprises the following steps:

[0057]

[0058] Y is selected from -F, -Cl, -Br or -I.

[0059] In a third aspect, the present application provides an organic electroluminescent device, comprising an anode, a cathode and an organic thin film layer arranged between the anode and the cathode.

[0060] The material of the organic thin film layer comprises the benzanthraoxanthrene compound as described in the first aspect.

[0061] As a preferred technical solution of the present application, the organic thin film layer comprises a light-emitting layer, and the material of the light-emitting layer comprises the benzanthraoxanthrene compound as described in the first aspect.

[0062] Preferably, the material of the light-emitting layer comprises a host material, and the host material comprises the benzanthraoxanthrene compound as described in the first aspect.

[0063] In a fourth aspect, the present application provides a display device, comprising the organic electroluminescent device as described in the third aspect.

[0064] Compared with the prior art, the present application has the following beneficial effects:

[0065] The benzanthraoxanthrene compound provided by the application can be used as a host material of a light-emitting layer of an organic electroluminescent device, and thus an organic electroluminescent device with lower driving voltage, higher current efficiency and longer service life is obtained. DETAILED DESCRIPTION

[0066] In order to facilitate the understanding of the present application, the present application is illustrated by the following examples. It should be understood by those skilled in the art that the examples are only used to help understand the present application, and should not be regarded as a specific limitation on the present application.

[0067] Synthesis Example 1

[0068] The present synthesis example provides compound 1, and the synthesis method is as follows:

[0069]

[0070] (1) Synthesis of intermediate 1-0 (1-bromo-10-iodoanthracene)

[0071] In a 250 mL three-necked flask, DMF (100 mL) was added, then 1-bromoanthracene (2.57 g) was added, and the temperature was increased to 35°C under stirring, then N-iodosuccinimide solid (2.3 g) was added in batches, after the addition was completed, the reaction was carried out at 35°C for 2 h, then the temperature was increased to 45°C for 4 h, and then the temperature was increased to 65°C for 1 h, and then the temperature was decreased to room temperature, water and chloroform were added for separation, then the organic layer was washed with water, and then magnesium sulfate was dried, then the magnesium sulfate was filtered off, and then concentrated to dryness, and then separated by silica gel column chromatography, and then eluted with petroleum ether to obtain the compound shown in intermediate 1-0 (1.8 g).

[0072] Mass spectrometry was performed on the obtained compound shown in intermediate 1-0: the two peaks with the largest mass-to-charge ratio (m / z) were 381.89 and 383.88, and the molecular formula of the product was determined as C 14 H8BrI.

[0073] Nuclear magnetic resonance was performed on the obtained intermediate 1-0: 1H-NMR (Switzerland Bruker Company, Avance Ⅱ 400MHz nuclear magnetic resonance spectrometer, CDCl3), δ 8.88 (d, 1H), δ 8.27 (m, 1H), δ 7.99 (m, 1H), δ 7.82 (m, 1H), δ 7.55 (m, 1H), δ 7.43 (m, 1H) δ 7.36-7.34 (m, 2H).

[0074] (2) Synthesis of intermediate 1-1

[0075] Into a 250 mL three-necked flask, 60 mL of toluene, 10 mL of ethanol and 5 mL of water were added under nitrogen protection, then intermediate 1-0 (3.83 g), phenyl boronic acid (1.22 g), sodium carbonate (2.12 g, 0.02 mol) and Pd(PPh3)4 (0.115 g, 0.0001 mol) were added, the temperature was slowly increased to 50 °C and reacted for 2 h, then the temperature was increased to 70 °C and reacted for 6 h, the temperature was decreased to room temperature, water was added for liquid separation, the organic layer was washed with water, then magnesium sulfate was added for drying, the magnesium sulfate was removed by filtration, the solvent was removed under reduced pressure, and the product was separated by silica gel column chromatography with petroleum ether elution to obtain intermediate 1-1 (2.0 g).

[0076] Mass spectrometry was performed on intermediate 1-1: the two peaks with the largest mass-to-charge ratio (m / z) were 332.02 and 334.02, and the molecular formula of the product was determined to be: C 20 H 13 Br.

[0077] (3) Synthesis of intermediate 1-2

[0078] Under nitrogen protection, 200 mL of n-butanol, intermediate 1-1 (3.33 g), 1,8-dichloro-2-naphthol (2.13 g), anhydrous potassium carbonate (1.4 g), cuprous iodide (0.02 g), and o-phenanthroline (0.3 g, CAS: 5144-89-8) were added to a 500 mL three-necked flask, and the mixture was heated to reflux for 60 h, the temperature was decreased to 0 °C, and the solid was filtered to obtain a solid, which was added to a mixture of dichloromethane and water, stirred for 10 min, and then separated, the organic layer was washed with water until neutral, dried with magnesium sulfate, the drying agent was removed by filtration, concentrated to dryness, and crystallized with toluene to obtain intermediate 1-2 (2.8 g).

[0079] Mass spectrometry was performed on intermediate 1-2: the mass-to-charge ratio (m / z) was 464.07.

[0080] (4) Synthesis of compound 1

[0081] Under nitrogen protection, 300 mL of DMF, sodium tert-butoxide (5.2 g), Pd(dba)2 (bis(benzonitrile)palladium, 0.08 g), and PdCl2 (0.012 g) were added to a 500 mL three-necked flask, and the temperature was increased to reflux for 24 h, the temperature was decreased to room temperature, water and toluene were added, the organic layer was washed with water until neutral, dried with magnesium sulfate, the drying agent was removed by filtration, concentrated to dryness, and separated by silica gel column chromatography with petroleum ether: ethyl acetate = 20:1 (volume ratio) elution to obtain compound 1 (6.5 g).

[0082] Mass spectrometry was performed on compound 1: the mass-to-charge ratio (m / z) was 392.12.

[0083] Synthesis Example 2-7

[0084] Synthesis of compound 2-7 was carried out according to the method of synthesis of compound 1, except that phenylboronic acid was replaced by an equimolar amount of the corresponding boronic acid compound (see Table 1), to obtain the corresponding bromide intermediate (see Table 1), which was then reacted with 1,8-dichloro-2-naphthol to obtain the chloro intermediate (see Table 1), which was subjected to intramolecular coupling to obtain compound 2-7 (see Table 1). The intermediates and compound 2-7 were subjected to mass spectrometry, and the results are shown in Table 1.

[0085] Table 1

[0086]

[0087]

[0088] Synthesis Example 8

[0089] This synthesis example provides compound 8, which is synthesized according to the following method:

[0090]

[0091] (1) Synthesis of intermediate Br-1

[0092] Into a 500 mL three-necked flask was added 200 mL of DMF, followed by compound 1 (4.0 g) and N-bromosuccinimide solid (1.8 g) added in portions at 25°C. After the addition was completed, the reaction was carried out at 25°C for 2 h, and then the temperature was raised to 45°C for 6 h. After cooling to room temperature, the reaction mixture was separated into water and chloroform. The organic layer was washed with water, dried over magnesium sulfate, and concentrated to dryness. The residue was separated by silica gel column chromatography using petroleum ether as the eluent to obtain the compound shown in intermediate Br-1 (2.8 g).

[0093] The compound shown in intermediate Br-1 was subjected to mass spectrometry, and the two peaks with the largest mass-to-charge ratio (m / z) were 470.03 and 472.03, which confirmed that the molecular formula of the product was C 30 H 15 BrO.

[0094] The compound shown in intermediate Br-1 was subjected to nuclear magnetic resonance detection: 1H-NMR (Switzerland Bruker Company, Avance II 400 MHz nuclear magnetic resonance spectrometer, CDCl3), δ 8.16 (m, 2H), δ 8.02 (m, 1H), δ 7.88 (s, 1H), δ 7.72-7.64 (m, 3H), δ 7.56-7.52 (m, 3H), δ 7.50-7.40 (m, 4H) δ 7.20 (m, 1H).

[0095] (2) Synthesis of compound 8​

[0096] In a 250 mL three-necked flask, 100 mL of dioxane, 10 mL of water, intermediate Br-1 (4.7 g), 2-naphthaleneboronic acid (1.7 g), sodium carbonate (2.12 g, 0.02 mol) and tetrakis triphenylphosphine palladium (0.115 g, 0.0001 mol) were sequentially added under nitrogen protection, and then the mixture was slowly warmed to 100°C for 12 h. After cooling to room temperature, the mixture was partitioned between water and toluene, and the organic layer was washed with water until neutral. The mixture was dried over magnesium sulfate, filtered and concentrated to dryness. The residue was separated by silica gel column chromatography using petroleum ether as eluent to obtain compound 8 (4.1 g).

[0097] Mass spectrometry was performed on compound 8, and the mass-to-charge ratio (m / z) was 518.17.

[0098] Synthesis Examples 9-16

[0099] Synthesis Examples 9-16 each provide a compound 9-16, which is synthesized according to the method for synthesizing compound 8, except that 2-naphthaleneboronic acid is replaced by an equimolar amount of a corresponding boronic acid compound (see Table 2 for details), to obtain the corresponding compound 9-16, which is subjected to mass spectrometry (see Table 2 for details).

[0100] Table 2

[0101]

[0102]

[0103]

[0104] Synthesis Example 17

[0105] This synthesis example provides compound 17, which is synthesized according to the following method:

[0106]

[0107] (1) Synthesis of intermediate Br-2

[0108] The synthesis method of intermediate Br-1 is followed, except that compound 1 is replaced by an equimolar amount of compound 2, to obtain intermediate Br-2 (1.6 g).

[0109] Mass spectrometry was performed on the obtained compound of intermediate Br-2, and the two peaks with the largest mass-to-charge ratio (m / z) were 520.05 and 522.04, indicating that the molecular formula of the product is C 34 H 17 BrO.

[0110] (2) Synthesis of compound 17

[0111] Referring to the synthesis of compound 8, the only difference is that intermediate Br-1 is replaced by an equivalent amount of intermediate Br-2 to obtain compound 17.

[0112] The obtained compound 17 is subjected to mass spectrometry detection: the mass-to-charge ratio (m / z) is 568.18.

[0113] Synthesis Examples 18-21

[0114] Synthesis Examples 18-21 respectively provide compounds 18-21, the synthesis of which refers to the synthesis of compound 17, the only difference being that 2-naphthalene boronic acid is replaced by an equivalent amount of the corresponding boronic acid compound (see Table 3 for details), to prepare the corresponding compound 18-21, which is subjected to mass spectrometry test (see Table 3 for details).

[0115] Table 3

[0116]

[0117]

[0118] Synthesis Example 22

[0119] Synthesis Example 22 provides compound 22, the synthesis of which is as follows:

[0120]

[0121] (1) Synthesis of intermediate Br-4

[0122] Referring to the synthesis of intermediate Br-1, the only difference is that compound 1 is replaced by an equivalent amount of compound 4 to obtain intermediate Br-4 (2.1 g).

[0123] The obtained intermediate Br-4 is subjected to mass spectrometry detection: the two peaks with the largest mass-to-charge ratio (m / z) are 546.06 and 548.06, and the molecular formula of the product is determined to be C 36 H 19 BrO.

[0124] (2) Synthesis of compound 22

[0125] Referring to the synthesis of compound 8, the only difference is that intermediate Br-1 is replaced by an equivalent amount of intermediate Br-4 to obtain compound 22.

[0126] The obtained compound 22 is subjected to mass spectrometry detection: the mass-to-charge ratio (m / z) is 594.20.

[0127] Synthesis Examples 23-26

[0128] Synthesis Example 23-26 provides compounds 23-26, respectively, by referring to the synthesis method of compound 22, except that 2-naphthylboronic acid is replaced by an equivalent amount of the corresponding boronic acid compound (see Table 4 for details), to produce the corresponding compound 23-26, which is subjected to mass spectrometry (see Table 4 for details).

[0129] Table 4

[0130]

[0131]

[0132] Synthesis Example 27

[0133] Synthesis Example 27 provides compound 27, by referring to the following synthesis method:

[0134]

[0135] (1) Synthesis of intermediate Br-6

[0136] Referring to the synthesis method of intermediate Br-1, except that compound 1 is replaced by an equivalent amount of compound 6, to produce intermediate Br-6 (0.3 g).

[0137] The obtained intermediate Br-6 is subjected to mass spectrometry: the two peaks with the largest mass-to-charge ratio (m / z) are 560.04 and 562.04, and the molecular formula of the product is determined to be C 36 H 17 BrO2.

[0138] (2) Synthesis of compound 27

[0139] Referring to the synthesis method of compound 8, except that intermediate Br-1 is replaced by an equivalent amount of intermediate Br-6, and 2-naphthylboronic acid is replaced by an equivalent amount of phenylboronic acid, to produce compound 27.

[0140] The obtained compound 27 is subjected to mass spectrometry: the mass-to-charge ratio (m / z) is 558.16.

[0141] Synthesis Examples 28-29

[0142] Synthesis Examples 28-29 provide compounds 28-29, respectively, by referring to the synthesis method of compound 27, except that phenylboronic acid is replaced by an equivalent amount of the corresponding boronic acid compound (see Table 5 for details), to produce the corresponding compound 28-29, which is subjected to mass spectrometry (see Table 5 for details).

[0143] Table 5

[0144]

[0145] Synthesis Example 30

[0146] This synthesis example provides compound 30, the synthesis method of which is as follows:

[0147]

[0148] (1) Synthesis of intermediate Br-7

[0149] Referring to the synthesis method of intermediate Br-1, the only difference is that compound 1 is replaced by an equal amount of compound 7 to obtain intermediate Br-7 (0.9 g).

[0150] Mass spectrometry is performed on the obtained compound of intermediate Br-7: the two peaks with the largest mass-to-charge ratio (m / z) are 586.09 and 588.09, and the molecular formula of the product is determined to be C 39 H 23 BrO.

[0151] (2) Synthesis of compound 30

[0152] Referring to the synthesis method of compound 8, the only difference is that intermediate Br-1 is replaced by an equal amount of intermediate Br-7, and 2-naphthalene boronic acid is replaced by an equal amount of phenyl boronic acid to obtain compound 30.

[0153] Mass spectrometry is performed on the obtained compound 30: the mass-to-charge ratio (m / z) is 584.21.

[0154] Synthesis Examples 31-32

[0155] Synthesis Examples 31-32 respectively provide compounds 31-32, the synthesis method of which refers to the synthesis method of compound 30, the only difference being that phenyl boronic acid is replaced by an equal amount of the corresponding boronic acid compound (see Table 6 for details) to prepare the corresponding compound 31-32, which is subjected to mass spectrometry (see Table 6 for details).

[0156] Table 6

[0157]

[0158] Synthesis Example 33

[0159] This synthesis example 33 provides compound 33, the synthesis method of which is as follows:

[0160]

[0161] (1) Synthesis of intermediate 33-1

[0162] The synthesis method of intermediate 1-1 is referred to, except that benzene boronic acid is replaced by deuterated 2-naphthalene boronic acid in equal amount of substance to obtain intermediate 33-1.

[0163] The compound shown in obtained intermediate 33-1 is detected by mass spectrometry: the two peaks with the largest mass-to-charge ratio (m / z) are 389.08 and 391.08, and the molecular formula of the product is determined as C 24 H8D7Br.

[0164] (2) Synthesis of intermediate 33-2

[0165] The synthesis method of intermediate 1-2 is referred to, except that intermediate 1-1 is replaced by intermediate 33-1 in equal amount of substance to obtain intermediate 33-2.

[0166] Intermediate 33-2 is detected by mass spectrometry: the mass-to-charge ratio (m / z) is 521.13.

[0167] (3) Synthesis of compound 33

[0168] The synthesis method of compound 1 is referred to, except that intermediate 1-2 is replaced by intermediate 33-2 in equal amount of substance to obtain compound 33.

[0169] Compound 33 is detected by mass spectrometry: the mass-to-charge ratio (m / z) is 449.18.

[0170] Synthesis Example 34

[0171] This synthesis example 34 provides compound 34, and the synthesis method is as follows:

[0172]

[0173] (1) Synthesis of intermediate Br-33

[0174] The synthesis method of compound Br-1 is referred to, except that compound 1 is replaced by compound 33 in equal amount of substance to obtain intermediate Br-33.

[0175] The compound shown in obtained intermediate Br-33 is detected by mass spectrometry: the two peaks with the largest mass-to-charge ratio (m / z) are 527.09 and 529.09, and the molecular formula of the product is determined as C 34 H 10 D7BrO.

[0176] (2) Synthesis of compound 34

[0177] Referring to the synthesis method of compound 8, the only difference is that intermediate Br-1 is replaced by an equal amount of intermediate Br-33, and 2-naphthalene boronic acid is replaced by an equal amount of phenyl boronic acid to obtain compound 34.

[0178] Mass spectrometry is performed on the obtained compound 34: the mass-to-charge ratio (m / z) is 525.21.

[0179] Synthesis Example 35

[0180] The present synthesis example 35 provides compound 35, the synthesis method of which is as follows:

[0181]

[0182] Referring to the synthesis method of compound 8, the only difference is that intermediate Br-1 is replaced by an equal amount of intermediate Br-33, and 2-naphthalene boronic acid is replaced by an equal amount of 1-naphthalene boronic acid to obtain compound 35.

[0183] Mass spectrometry is performed on the obtained compound 35: the mass-to-charge ratio (m / z) is 575.23.

[0184] Other compounds not specifically listed in the synthesis steps can be prepared by combining the above examples with common knowledge in the art.

[0185] The specific structures of several materials used in the device examples of the present application are as follows:

[0186]

[0187] Device Example 1

[0188] The present device example provides an organic electroluminescent device, wherein the main body material of the light-emitting layer of the organic electroluminescent device is compound 2 provided in synthesis example 2 of the present application.

[0189] The structure of the organic electroluminescent device is: ITO / HT (100 nm) light-emitting layer (30 nm): BH: BD-33% / TPBI (30 nm) / LiF (0.5 nm) / Al (150 nm).

[0190] The preparation process of the organic electroluminescent device is as follows:

[0191] The glass substrate coated with an ITO transparent conductive layer (as an anode) is subjected to ultrasonic treatment in a cleaning agent, then rinsed in deionized water, then ultrasonic oil removal in a mixed solvent of acetone and ethanol, then baked in a clean environment until completely water-free, washed with ultraviolet light and ozone, and the surface is bombarded with a low-energy cation beam to improve the surface properties and improve the binding ability with the hole layer.

[0192] The material was placed in a vacuum chamber, vacuumed to 1x10-5~1x10-6Pa, and vacuum evaporated onto a cleaned ITO substrate. Among them, the light-emitting layer (30 nm): BH:BD-1 3% means that in the device, BH and BD-3 are co-evaporated to form a light-emitting layer at a volume ratio of 97:3, and the thickness of the light-emitting layer is 30 nm. TPBI is an electron transport layer, LiF is an electron injection layer, and BH is a light-emitting layer host material (compound 2 in this embodiment).

[0193] Device Example 2-21

[0194] Device Example 2-21 respectively provides an organic electroluminescence device, which is only different from Device Example 1 in that the light-emitting layer host material is different (see Table 7 below for details), and the other conditions are the same as those of Device Example 1.

[0195] Device Comparative Example 1-2

[0196] Device Comparative Example 1-2 respectively provides an organic electroluminescence device, which is only different from Device Example 1 in that the light-emitting layer host material is different (see Table 7 below for details), and the other conditions are the same as those of Device Example 1.

[0197] Performance Test

[0198] Test method: The OLED-1000 multi-channel accelerated aging life and light color performance analysis system produced by Hangzhou Yuanfang was used to test the current efficiency and life LT90 of the OLED device provided above; wherein LT90 refers to the time required for the luminance to drop to 90% of the original luminance while keeping the current density unchanged at the initial luminance of 2000 nit, wherein the current efficiency and LT90 are relative values.

[0199] The test results of the performance of the above organic electroluminescence device are shown in Table 7 below:

[0200] Table 7

[0201]

[0202]

[0203] From the content of Table 7, it can be seen that by designing the structure of the benzanthracene-oxanthrene compound, further by selecting a mother nucleus containing an oxygen atom The obtained benzanthracene-oxanthrene compound can be used as a host material for the light-emitting layer of an organic electroluminescence device, thereby obtaining an organic electroluminescence device with lower driving voltage, higher current efficiency and longer life.

[0204] Applicant states that the detailed process flow of the present application is illustrated by the above-mentioned examples, but the present application is not limited to the above-mentioned detailed process flow, i.e. it does not mean that the present application must rely on the above-mentioned detailed process flow to be implemented. It should be understood by those skilled in the art that any improvement of the present application, equivalent replacement of each raw material of the product of the present application, addition of auxiliary ingredients, selection of specific modes, etc. fall within the protection scope and disclosure scope of the present application.

Claims

1. A benzanthrophenonexanthracene compound, characterized in that, The benzoxanthroxanthracene compounds have the structure shown in formula BHI: Formula BHI; Among them, Ar 101 and Ar 102 Each is independently selected from any one of substituted or unsubstituted C6-C40 aryl groups or substituted or unsubstituted C12-C20 heteroaryl groups; m and n are each independently selected from 0 or 1, and m and n are not both 0 at the same time; Ar 101 Ar 102 The substituents described herein are each independently selected from any one or a combination of at least two of -D, -F, -CN, C1~C12 alkyl, C1~C6 alkoxy, and C6~C20 aryl; The C12~C20 heteroaryl group is selected from any one of dibenzofuranyl, dibenzothiophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, dinaphthofuranyl, and dinaphthothiophenyl; In the benzo[a]anthraxanthranate compound represented by formula BHI, the hydrogen atom can be replaced by a deuterium atom.

2. The benzanthrophenonexanthracene compound according to claim 1, characterized in that, The C6-C40 aryl group is selected from any one of phenyl, diphenyl, terphenyl, naphthyl, anthracene, phenanthrene, fluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, naphthyl, pyrene, perylene, spirofluorenyl, triphenylene, fluoranyl, ind[a]fluorenyl, benzo[a]ind[a]fluorenyl, dibenzo[a]ind[a]fluorenyl, naphthyl, or benzo[a]naphthylfluorenyl.

3. The benzanthrophenone class of compounds according to claim 1, characterized in that, The C1-C12 alkyl group is selected from any one of methyl, ethyl, propyl, butyl, or adamantyl.

4. The benzanthrophenonexanthracene compound according to claim 1, characterized in that, The C1-C6 alkoxy groups are selected from any one of methoxy, ethoxy, propoxy, or butoxy.

5. The benzanthrophenonexanthracene compound according to claim 1, characterized in that, The C6-C20 aryl group is selected from any one of phenyl, diphenyl, naphthyl, 9,9-dimethylfluorenyl, fluoranyl, or triphenylene.

6. The benzanthrophenonexanthracene compound according to claim 1, characterized in that, The Ar 101 Selected from any one of the following substituted or unsubstituted groups: phenyl, naphthyl, diphenyl, 9,9-dimethylfluorenyl, dibenzofuranyl or dibenzothiopheneyl; The substituents are selected from any one of methyl, ethyl, propyl, tert-butyl, methoxy, ethoxy, propoxy, butoxy, adamantyl, -D, -F, -CN or phenyl.

7. The benzanthrophenonexanthracene compound according to claim 1, characterized in that, The Ar 102 Selected from any one of the following substituted or unsubstituted groups: phenyl, naphthyl, diphenyl, 9,9-dimethylfluorenyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzofluorenyl, fluorenyl, triphenylene, triphenyl, anthracene, phenanthrene, 9,9-diphenylfluorenyl, spirofluorenyl or indenefluorenyl; The substituent is selected from any one of phenyl, naphthyl, fluoranyl, or triphenylene.

8. The benzanthrophenonexanthracene compound according to claim 1, characterized in that, The benzoxanthraxanthracene compounds are selected from any one of the following substituted or unsubstituted compounds: ； X is O; The substitution refers to the replacement of at least one hydrogen atom in the above compound with a deuterium atom.

9. An intermediate, characterized in that, The intermediate is selected from any one of the following compounds: 、 、 、 、 ； Among them, Ar 101 It has the same scope of protection as claim 1; Y is selected from -F, -Cl, -Br, or -I; The intermediate is used to prepare the benzanthrophenonexanthracene compound as described in any one of claims 1-8.

10. The intermediate according to claim 9, characterized in that, The intermediate is selected from any one of the following compounds: 、 、 、 、 ； Among them, Ar 101 Selected from , , , , , , or The dashed line represents the connection point; Y is selected from -F, -Cl, -Br, or -I; The intermediate is used to prepare the benzanthrophenonexanthracene compound as described in any one of claims 1-8.

11. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode; The organic thin film layer includes a light-emitting layer, and the material of the light-emitting layer includes a host material, which includes a benzene-anthraxonoanthracene compound as described in any one of claims 1-8.

12. A display device, characterized in that, The display device includes the organic electroluminescent device as described in claim 11.

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