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

Abstract

The application provides a benzanthanthrene-oxanthrene compound, an organic electroluminescent device and a display device. The benzanthanthrene-oxanthrene compound has a structure as shown in formula BDI. The benzanthanthrene-oxanthrene compound provided by the application can be used as an organic thin film layer material of an OLED device, and can further be used as a light-emitting layer doping material. Therefore, the organic electroluminescent device prepared has a lower driving voltage, a higher current efficiency and a longer service life.

Description

TECHNICAL FIELD

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

[0002] At present, organic electroluminescent (OLED) display technology has been applied in the fields of smart phones, tablet computers and the like, and will further be extended to large-size application fields such as televisions. In the development process in the past 30 years, 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 OLEDs has been accelerated, so that OLEDs have been widely applied in the fields of display and lighting.

[0003] The selection of the hole layer, the light-emitting layer and other organic functional layer materials also has a great influence on the current efficiency, driving voltage and life of the device, and currently, functional layer materials with higher performance are still being explored.

[0004] Therefore, in order to meet the higher requirements of people for OLED devices, more types and higher performance of OLED materials need to be developed in the field. SUMMARY

[0005] In view of the deficiencies of the prior art, the purpose of the present application is to provide a benzanthroxanthene compound, an organic electroluminescent device and a display device. The benzanthroxanthene compound provided by the present application can be used as an organic thin film layer material of an OLED device, and further can be used as a light-emitting layer doping material, so that the organic electroluminescent device prepared therefrom has a lower driving voltage, higher current efficiency and longer service life.

[0006] To achieve this purpose, the present application adopts the following technical solutions:

[0007] In a first aspect, the present application provides a benzanthroxanthene compound, characterized in that the benzanthroxanthene compound has a structure as shown in formula BDI:

[0008]

[0009] wherein Ar 101 , Ar 102 , Ar 201 , Ar 202 are each independently selected from any one of a substituted or unsubstituted C6-C40 aryl group and a substituted or unsubstituted C12-C20 heteroaryl group;

[0010] m is selected from 0 or 1;

[0011] Ar101 Ar 102 Ar 201 Ar 202 The substituent in the substituent group is selected from any one or combination of at least two of -D, -F, -CN, C1-C12 alkyl, C1-C6 alkoxy, C6-C20 aryl, and C12-C20 heteroaryl.

[0012] The benzoxanthrene compound provided by the application can be used as an organic thin film layer material of an OLED device, and can further be used as a light-emitting layer doping material, an electron blocking layer material, or a hole transport layer material. The organic electroluminescent device prepared therefrom has a lower driving voltage, higher current efficiency, and longer service life.

[0013] Ar 101 Ar 102 Ar 201 Ar 202 Each is independently selected from any one of a substituted or unsubstituted C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.) aryl group, and a substituted or unsubstituted C12-C20 (e.g., C12, C14, C16, C18, or C20, etc.) heteroaryl group.

[0014] Ar 101 Ar 102 Ar 201 Ar 202 The substituent in the substituent group is selected from any one or combination of at least two of -D (deuterium atom), -F, -CN, C1-C12 (e.g., C1, C2, C4, C6, C10, or C12, etc.) alkyl, (e.g., C1, C2, C4, or C6, etc.) alkoxy, a substituted or unsubstituted C6-C20 (e.g., C6, C8, C10, C12, C16, or C20, etc.) aryl group, and a substituted or unsubstituted C12-C20 (e.g., C12, C14, C16, C18, or C20, etc.) heteroaryl group.

[0015] It should be noted that when m is 0, the benzoxanthrene compound represented by formula BDI does not have a group (the dotted line represents a connection site, and the same applies hereinafter).

[0016] The following are preferred technical solutions of the application, but not as a limitation on the technical solutions provided by the application. Through the following preferred technical solutions, the purposes and beneficial effects of the 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, 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, cyclopentyl, cyclohexyl, methylcyclohexyl, methylcyclopentyl, 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, 9,9-dimethylfluorenyl, naphthyl, fluoranthenyl, or triphenylenyl.

[0022] As a preferred technical solution of the present application, the Ar 101 and Ar 101 are each independently selected from any one of the following substituted or unsubstituted groups: phenyl, naphthyl, biphenyl, dibenzofuranyl, 9,9-dimethylfluorenyl, terphenyl, fluoranthenyl, naphthobenzofuranyl, benzofluorenyl;

[0023] the substituted substituent is selected from at least one of phenyl, methyl, adamantyl, tert-butyl, 1-hexylcyclopentyl, cyclopentyl, cyclohexyl, naphthyl, dibenzothiophenyl, dibenzofuranyl, naphthobenzothiophenyl, naphthobenzofuranyl, -F, -CN, -D, methoxy;

[0024] wherein the dotted line represents a connection site.

[0025] Preferably, the Ar 101 and Ar 101 are each independently selected from any one of the following groups:

[0026] wherein the dotted line represents a connection site.

[0027] As a preferred technical solution of the present application, the Ar 201 and Ar202 each independently is selected from any one or a combination of at least two of the following substituted or unsubstituted groups: phenyl, naphthyl, dibenzofuranyl or biphenyl;

[0028] the substituted substituent is selected from any one or a combination of at least two of the following groups: methyl, methoxy, phenyl or dibenzofuranyl.

[0029] Preferably, the Ar 201 and Ar 202 each independently is selected from any one or a combination of at least two of the following groups: phenyl, naphthyl, dibenzofuranyl or biphenyl; or dibenzofuranyl.

[0030] wherein the dotted line indicates a connection site.

[0031] As a preferred technical solution of the present application, the benzanthraoxanthrene compound is selected from any one of the following substituted or unsubstituted compounds:

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044] The substitution refers to that at least one hydrogen atom in the above-mentioned compound is replaced by a deuterium atom.

[0045] It should be noted that the substitution refers to that at least one hydrogen atom in the above-mentioned compound is replaced by a deuterium atom, and the hydrogen atom on the mother nucleus is not replaced by a deuterium atom.

[0046] As a preferred technical scheme of the present application, the benzanthroxanthene compound is selected from any one of compounds 1-27:

[0047]

[0048] In the present application, the preparation method of the benzanthroxanthene compound shown in formula BDI is as follows:

[0049]

[0050] wherein, Ar 101 , Ar 102 , Ar 201 , Ar 202 has the same scope of protection as the first aspect;

[0051] X is selected from -Cl, -Br or -I.

[0052] In the second aspect, the present application provides an organic electroluminescent device, which comprises an anode, a cathode and an organic thin film layer arranged between the anode and the cathode.

[0053] The material of the organic thin film layer comprises the benzanthroxanthene compound as described in the first aspect.

[0054] As a preferred technical scheme of the present application, the organic thin film layer comprises a light-emitting layer, and the material of the light-emitting layer comprises the benzanthroxanthene compound as described in the first aspect.

[0055] Preferably, the material of the light-emitting layer comprises a doping material, and the doping material comprises the benzanthroxanthene compound as described in the first aspect.

[0056] In the third aspect, the present application provides a display device, which comprises the organic electroluminescent device as described in the second aspect.

[0057] Compared with the prior art, the present application has the following beneficial effects:

[0058] The benzanthroxanthene compound provided by the present application can be used as the material of the organic thin film layer of the OLED device, and further can be used as the doping material of the light-emitting layer, so that the organic electroluminescent device prepared therefrom has a lower driving voltage, a higher current efficiency and a longer service life. DETAILED DESCRIPTION

[0059] In order to facilitate the understanding of the present application, the present application is illustrated as follows. 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.

[0060] Synthesis Example 1

[0061] This synthetic example 1 provides compound 1, the synthesis method of which is as follows:

[0062]

[0063] (1) Synthesis of intermediate 1-0 (1-bromo-10-iodoanthracene)

[0064] Into a 250 mL three-necked flask, 100 mL of DMF was added, followed by 1-bromoanthracene (2.57 g), and the mixture was stirred and heated to 35°C. Then, N-iodosuccinimide solid (2.3 g) was added in portions. After the addition was completed, the mixture was reacted at 35°C for 2 h, then heated to 45°C for 4 h, and then heated to 65°C for 1 h. After cooling to room temperature, the mixture was separated with water and chloroform. After washing the organic layer with water, it was dried over magnesium sulfate. After filtering off the magnesium sulfate, the mixture was concentrated to dryness, and then separated by silica gel column chromatography using petroleum ether as the eluent to obtain the compound shown in intermediate 1-0 (1.8 g).

[0065] Mass spectrometry was performed on the obtained compound shown in intermediate 1-0, and the two peaks with the largest mass-to-charge ratio (m / z) were 381.89 and 383.88, which determined the molecular formula of the product to be C 14 H8BrI.

[0066] NMR was performed on the obtained intermediate 1-0: 1H-NMR (Swiss Bruker Company, Avance Ⅱ 400 MHz 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).

[0067] (2) Synthesis of intermediate 1-1

[0068] Under nitrogen protection, 100 mL of dry toluene, intermediate 1-0 (3.83 g), diphenylamine (1.7 g), Pd(dba)2 (bisbenzylideneacetone palladium, 0.0575 g, 0.0001 mol), 10% by mass of tri-tert-butyl phosphine in toluene (0.4 g of the toluene solution of tri-tert-butyl phosphine, 0.0002 mol of tri-tert-butyl phosphine), and sodium tert-butoxide (1.44 g, 0.015 mol) were added into a 250 mL three-necked flask. The mixture was heated to 40°C for 2 h, then heated to 60°C for 8 h, and then cooled to room temperature. After adding water to separate the mixture, the organic layer was washed with water until it was neutral, dried over magnesium sulfate, and then concentrated to dryness. The mixture was separated by silica gel column chromatography using petroleum ether as the eluent to obtain intermediate 1-1 (1.7 g).

[0069] The intermediate 1-1 was subjected to mass spectrometry detection: the two peaks with the largest mass-to-charge ratio (m / z) were 423.06 and 425.06, and the molecular formula of the product was determined to be C 26 H 18 BrN.

[0070] The intermediate 1-1 was subjected to elemental analysis, and the calculated percentage content of each element was: C, 73.59%; H, 4.28%; Br, 18.83%; N, 3.30%; and the actually measured values were: C, 73.62%; H, 4.27%; N, 3.29%.

[0071] (3) Synthesis of intermediate 1-2

[0072] Under nitrogen protection, 200 mL of n-butanol, intermediate 1-1 (4.24 g), 1,8-dichloro-2-naphthol (2.13 g), anhydrous potassium carbonate (1.4 g), cuprous iodide (0.02 g), o-phenanthroline (0.3 g, CAS: 5144-89-8) were added into a 500 mL three-necked flask, and the reaction was heated to reflux for 60 hours. The temperature was lowered to 0°C, and a solid was obtained by filtration. The solid was added into a mixture of dichloromethane and water, and stirred for 10 minutes before being separated. The organic layer was washed with water until neutral, dried over magnesium sulfate, and concentrated to dryness. A mixture of toluene and ethanol was used for crystallization to obtain intermediate 1-2 (3.9 g).

[0073] The intermediate 1-2 was subjected to mass spectrometry detection: the mass-to-charge ratio (m / z) was 555.12.

[0074] (4) Synthesis of compound 1

[0075] Under nitrogen protection, intermediate 1-2 (9 g), DMF (280 mL), sodium tert-butoxide (5.0 g), Pd(dba)2 (bisbenzaldehyde palladium, 0.08 g), PdCl2 (0.012 g) were added into a 500 mL three-necked flask, and the reaction was heated to reflux for 48 hours. The temperature was lowered to room temperature, and a mixture of water and toluene was added. The organic layer was washed with water until neutral, dried over magnesium sulfate, and concentrated to dryness. Silica gel column chromatography was used for separation, and petroleum ether: ethyl acetate = 20:1 (volume ratio) was used for elution to obtain compound 1 (5.1 g).

[0076] The compound 1 was subjected to mass spectrometry detection: the mass-to-charge ratio (m / z) was 483.16.

[0077] Synthesis Example 2-20

[0078] Synthesis Example 2-20 provides compound 2-20, respectively, the synthesis method of which refers to the synthesis method of compound 1, the difference being that the diphenylamine is replaced by the amount-of-substance diphenylamine compound (see Table 1 for details), to prepare the bromide intermediate, then the bromide intermediate and 1,8-dichloro-2-naphthol are reacted to obtain the chloro intermediate, the chloro intermediate is subjected to intramolecular coupling reaction to obtain the final compound 2-20, and each intermediate and compound 2-20 are subjected to mass spectrometry test, and the test structure is shown in Table 1 and Table 2.

[0079] Table 1

[0080]

[0081]

[0082]

[0083]

[0084] Table 2

[0085]

[0086]

[0087]

[0088]

[0089] Synthesis Example 21

[0090] The synthesis example provides compound 21, the synthesis method of which is as follows:

[0091]

[0092] (1) Synthesis of intermediate 21-1

[0093] In a 500 mL three-necked flask, DMF (200 mL) was added, then compound 1 (4.8 g) was added, N-bromosuccinimide solid (1.8 g) was added in batches at 15 °C, after the addition was completed, the reaction was carried out at 15 °C for 2 h, then the temperature was increased to 25 °C and the reaction was carried out for 4 h, the temperature was decreased to room temperature, water and chloroform were added, the organic layer was washed with water, then magnesium sulfate was dried, after the magnesium sulfate was filtered off, it was concentrated to dryness, and then separated by silica gel column chromatography, eluted with petroleum ether, to obtain the compound shown in intermediate 21-1 (0.8 g), with a yield of 14%.

[0094] The obtained intermediate 21-1 was subjected to mass spectrometry test: the two peaks with the largest mass-to-charge ratio (m / z) were 561.07 and 563.07, and the molecular formula of the product was determined as C 36 H20 BrNO.

[0095] The obtained intermediate 21-1 was subjected to nuclear magnetic detection: 1H-NMR (Switzerland Bruker Company, Avance Ⅱ 400MHz nuclear magnetic resonance spectrometer, CDCl3), δ 8.17 (m, 2H), δ 7.86 (s, 1H), δ 7.71 (m, 1H), δ 7.55 (m, 2H), δ 7.50-7.40 (m, 3H), δ 7.24-7.16 (m, 5H) δ 7.10-6.97 (m, 6H).

[0096] (2) Synthesis of compound 21

[0097] Under the protection of nitrogen, 100 mL of dry toluene, intermediate 21-1 (5.6 g), diphenylamine (1.7 g), Pd(dba)2 (bisbenzaldehyde palladium, 0.0575 g, 0.0001 mol), 10% by mass of tri-tert-butyl phosphine in toluene (0.4 g of toluene solution of tri-tert-butyl phosphine, 0.0002 mol of tri-tert-butyl phosphine), and sodium tert-butoxide (1.44 g, 0.015 mol) were added to a 250 mL three-necked flask, heated to reflux, and reacted for 12 h. After cooling to room temperature, water was added for liquid separation, then the organic layer was washed with water until neutral, dried over magnesium sulfate, filtered to remove magnesium sulfate, concentrated to dryness, and separated by silica gel column chromatography eluted with petroleum ether: ethyl acetate = 20:1 (volume ratio) to obtain compound 21 (5.1 g).

[0098] Compound 21 was subjected to mass spectrometry detection: the mass-to-charge ratio (m / z) was 650.24.

[0099] Compound 21 was subjected to elemental analysis, and the calculated percentage of each element was: C, 88.59%; H, 4.65%; N, 4.30%; O, 2.46%; and the actual measured values were: C, 88.57%; H, 4.63%; N, 4.31%.

[0100] Synthesis Examples 22-24

[0101] Synthesis Examples 22-24 provide compounds 22-24, the synthesis method of which is referred to the synthesis method of compound 21, the only difference being that diphenylamine is replaced by an equal amount of a diarylamine compound (see Table 3 for details), and compounds 22-24 are subjected to mass spectrometry testing, and the test results are shown in Table 3:

[0102] Table 3

[0103]

[0104] Synthesis Example 25

[0105] The present synthesis example provides compound 25, the synthesis method of which is as follows:

[0106]

[0107] (1) Synthesis of intermediate 25-1

[0108] Referring to the synthesis method of intermediate 21-1, the only difference is that compound 1 is replaced by an equal amount of compound 10 to obtain intermediate 25-1 (2.2 g) with a yield of 37%.

[0109] Mass spectrometry is performed on the obtained intermediate 25-1: the two peaks with the largest mass-to-charge ratio (m / z) are 589.10 and 591.10, and the molecular formula of the product is determined to be C 38 H 24 BrNO.

[0110] (2) Synthesis of compound 25

[0111] Referring to the synthesis method of compound 21, the only difference is that intermediate 21-1 is replaced by an equal amount of intermediate 25-1 to obtain compound 25.

[0112] Mass spectrometry is performed on compound 25: the mass-to-charge ratio (m / z) is 678.27.

[0113] Synthesis examples 26-27

[0114] Synthesis examples 26-27 provide compounds 26-27, the synthesis method of which refers to the synthesis method of compound 25, the only difference being that diphenylamine is replaced by an equal amount of a diarylamine compound (see Table 4 for details), and mass spectrometry is performed on compounds 26-27, the test results of which are shown in Table 4:

[0115] Table 4

[0116]

[0117]

[0118] Other compounds not specifically listed in the synthesis steps can be prepared by common knowledge in the art in combination with the above examples.

[0119] The specific structures of several materials used in the device examples of the present application are as follows:

[0120]

[0121] Device example 1

[0122] The device embodiment provides an organic electroluminescent device, and a light-emitting layer doping material of the organic electroluminescent device is compound 2 provided by the application.

[0123] The organic electroluminescent device structure is: ITO / HT (100 nm) light-emitting layer (30 nm): BH:BD 3% / TPBI (30 nm) / LiF (0.5 nm) / Al (150 nm).

[0124] The preparation process of the organic electroluminescent device is as follows:

[0125] The material is placed in a vacuum chamber, vacuumized to 1x10 -5 ~1x10 -6 Pa, and vacuum evaporated onto the cleaned ITO substrate in sequence. Among them, the light-emitting layer (30 nm): BH:BD 3% means that in the device, BH and BD are co-evaporated to form a light-emitting layer with a volume ratio of 97:3, and the thickness of the light-emitting layer is 30 nm. BH is the main material of the light-emitting layer, and in this embodiment, BH is BH-1. BD is the doping material of the light-emitting layer, and in this embodiment, BD is compound 2.

[0126] TPBI is an electron transport layer, and LiF is an electron injection layer.

[0127] Device embodiment 2-17

[0128] Device embodiment 2-17 respectively provides an organic electroluminescent device, and the difference from device embodiment 1 is only that the light-emitting layer doping material is different (see Table 5 below), and the other conditions are the same as those of device embodiment 1.

[0129] Device comparative example 1-2

[0130] Device comparative example 1-2 respectively provides an organic electroluminescent device, and the difference from device embodiment 1 is only that the light-emitting layer doping material is different (see Table 5 below), and the other conditions are the same as those of device embodiment 1.

[0131] Performance test

[0132] Test method: The OLED-1000 multi-channel accelerated aging life and light color performance analysis system produced by Hangzhou Yuanfang is used to test the driving voltage, 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 driving voltage, current efficiency and LT90 are all relative values.

[0133] The test results of the performance of the above organic electroluminescent device are shown in Table 5 below:

[0134] Table 5

[0135]

[0136]

[0137] As shown in Table 5, this invention, through the design of the structure of benzene-anthraxonoanthracene compounds, further utilizes the selection of an oxygen-containing core. The obtained benzene-anthraxonoanthracene compounds can be used as doping materials for the light-emitting layer of organic electroluminescent devices, thereby obtaining organic electroluminescent devices with lower driving voltage, higher current efficiency and longer lifetime.

[0138] Device Example 18

[0139] This embodiment of the device provides an organic electroluminescent device, wherein the doping material of the light-emitting layer of the organic electroluminescent device is compound 2 provided by the present invention;

[0140] The structure of the organic electroluminescent device is as follows: ITO / HT (100nm) emitting layer (30nm): BH: BD3% / TPBI (30nm) / LiF (0.5nm) / Al (150nm).

[0141] The fabrication process of organic electroluminescent devices is as follows:

[0142] The material was placed inside a vacuum chamber, and the vacuum was evacuated to 1×10⁻⁶. -5 ~1×10 -6 Pa is sequentially vacuum-deposited onto the cleaned ITO substrate. The light-emitting layer (30nm): BH:BD 3% refers to the fact that BH and BD are co-evaporated in a volume ratio of 97:3 to form the light-emitting layer, with a thickness of 30nm. BH is the host material of the light-emitting layer; in this embodiment, BH is BH-b. BD is the dopant material of the light-emitting layer; in this embodiment, BD is compound 2.

[0143] TPBI is the electron transport layer, and LiF is the electron injection layer.

[0144] Device Examples 19-21

[0145] Device Examples 19-21 each provide an organic electroluminescent device, which differs from Device Example 18 only in that the host material (BH) of the light-emitting layer is different and the doping material of the light-emitting layer is different (see Table 6 below for details). Other conditions are the same as those in Device Example 18.

[0146] Performance testing

[0147] Test method: OLED-1000 multi-channel accelerated aging life and light color performance analysis system produced by Hangzhou Yurun was used to test the driving voltage, current efficiency and life LT90 of the OLED device provided above; wherein, the LT90 refers to the time required for the luminance to decrease to 90% of the original luminance while keeping the current density unchanged at the initial luminance of 2000 nit, wherein the driving voltage, current efficiency and LT90 are all relative values.

[0148] The test results of the performance of the organic electroluminescent device are shown in Table 6 below:

[0149] Table 6

[0150]

[0151] As can be seen from the content of Table 6, the benzanthraoxanthrene compound provided by the present application as a doping material of the light-emitting layer of the organic electroluminescent device can be used in cooperation with different host materials, and an organic electroluminescent device with lower driving voltage, higher current efficiency and longer life can be obtained.

[0152] When the benzanthraoxanthrene compound provided by the present application as a doping material of the light-emitting layer of the organic electroluminescent device is used with BH-b or BH-c as the host material of the light-emitting layer, the current efficiency and the life of the organic electroluminescent device can be further improved.

[0153] The applicant declares that the detailed process flow of the present application is illustrated by the above examples, but the present application is not limited to the above detailed process flow, that is, it does not mean that the present application must rely on the above 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 BDI: BDI (Body-Induced Difference); Among them, Ar 101 Ar 102 Ar 201 Ar 202 Each is independently selected from any one of substituted or unsubstituted C6-C40 aryl groups or substituted or unsubstituted C12-C20 heteroaryl groups; m is selected from 0 or 1; Ar 101 Ar 102 Ar 201 Ar 202 The substituents described herein are 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.

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, cyclopentyl, cyclohexyl, methylcyclohexyl, methylcyclopentyl, 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 and Ar 102 Each group is independently selected from any one of the following substituted or unsubstituted groups: phenyl, naphthyl, diphenyl, dibenzofuranyl, 9,9-dimethylfluorenyl, terphenyl, fluoranyl, naphthobenzofuranyl, benzofluorenyl; The substituents are selected from phenyl, methyl, adamantyl, tert-butyl, 1-hexylcyclopentyl, cyclopentyl, and cyclohexyl. At least one of naphthyl, -F, -CN, -D, and methoxy; The dashed lines represent connection points.

7. The benzanthrophenonexanthracene compound according to claim 1, characterized in that, The Ar 101 and Ar 102 Each group is independently selected from any one of the following groups: , , , , , , , , , , , , , , , or ; The dashed lines represent connection points.

8. The benzanthrophenone compound according to claim 1, characterized in that, The Ar 201 and Ar 202 Each group is independently selected from any one of the following substituted or unsubstituted groups: phenyl, naphthyl, dibenzofuranyl, or diphenyl; The substituents are selected from any one or a combination of at least two of methyl, methoxy, or phenyl.

9. The benzanthrophenonexanthracene compound according to claim 8, characterized in that, The Ar 201 and Ar 202 Each is independently selected from phenyl, Or any one of dibenzofuranyl; The dashed lines represent connection points.

10. A benzanthrophenonexanthracene compound, characterized in that, The benzoxanthraxanthracene compounds are selected from any one of the following substituted or unsubstituted compounds: ； The substitution refers to the replacement of at least one hydrogen atom in the above compound with a deuterium atom.

11. A benzanthrophenonexanthracene compound, characterized in that, The benzanthroxanthracene compounds are selected from any one of compounds 1-27: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 。 12. 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 doped material, wherein the doped material includes a benzene-anthraxonoanthracene compound as described in any one of claims 1-11.

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

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