Quinoxaline compound, intermediate and organic electroluminescent device

Abstract

The invention provides a quinoxaline compound, an intermediate and an organic electroluminescent device. The quinoxaline compound has a structure as shown in a formula I or a formula II. The structure of the quinoxaline compound is designed, so that the quinoxaline compound is suitable for being used as a main body material of a light-emitting layer of the organic light-emitting device, and the organic light-emitting device has relatively low driving voltage, relatively high current efficiency and relatively long service life.

Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescent materials, and particularly relates to a quinoxaline compound, an intermediate and an organic electroluminescent device. Background Art

[0002] The structure of an organic electroluminescent device specifically consists of an anode, a cathode, and an organic layer between them. To improve the efficiency and stability of organic electroluminescent elements, the organic material layer includes multiple layers made of different materials, such as a hole injection layer (HIL), a hole transport layer (HTL), a hole blocking layer, a light-emitting layer, an electron transport layer (ETL), and an electron injection layer (EIL). Currently, organic electroluminescence has become a mainstream display technology, and accordingly, various new OLED materials have also been developed.

[0003] In order to meet people's higher requirements for OLED devices, the field urgently needs to develop more types of materials to improve the performance of OLED devices in terms of current efficiency, lifespan, etc. Summary of the Invention

[0004] In response to the shortcomings of the prior art, the present invention provides a quinoxaline compound, an intermediate, and an organic electroluminescent device. The present invention designs the structure of the quinoxaline compound to make it suitable as a host material for the light-emitting layer of an organic electroluminescent device, thereby enabling the organic electroluminescent device to have a lower driving voltage, higher current efficiency, and longer life.

[0005] To achieve this object, the present invention adopts the following technical solutions:

[0006] In a first aspect, the present invention provides a quinoxaline compound having a structure shown in Formula I or Formula II below:

[0007]

[0008] Ar 11 Any one selected from a single bond, a C6-C30 arylene group or a C6-C20 heteroarylene group;

[0009] R 101 Any one selected from H, cyano (-CN), C6-C30 aryl or C6-C20 heteroaryl;

[0010] R1, R2, and R3 are each independently selected from any one of H, C6-C40 aryl, C6-C30 heteroaryl, or C1-C12 alkyl;

[0011] The hydrogen atoms in the quinoxaline compound can each independently be substituted by at least one of a deuterium atom (D), -CN, -F, a C6-C20 aryl group, a C6-C20 heteroaryl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a triphenylsilyl group or a triphenylmethyl group.

[0012] The present invention obtains a compound suitable for use as a main material of a light-emitting layer by designing the structure of a quinoxaline compound. The organic electroluminescent device prepared thereby has a lower driving voltage, a higher current efficiency and a longer service life.

[0013] In the present invention, the C6-C40 can be selected from C6, C10, C12, C18, C24, C30, C36 or C40.

[0014] The C6-C30 can be selected from C6, C10, C12, C18, C24 or C30, etc.

[0015] The C6-C20 can be selected from C6, C10, C12, C18 or C20, etc.

[0016] The C1-C12 may be selected from C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11 or C12.

[0017] The C1-C6 may be selected from C1, C2, C3, C4, C5 or C6.

[0018] In the present invention, "D" represents a deuterium atom, and the same shall apply hereinafter.

[0019] The following are preferred technical solutions of the present invention, but are not intended to limit the technical solutions provided by the present invention. Through the following preferred technical solutions, the objectives and beneficial effects of the present invention can be better achieved and realized.

[0020] As a preferred technical solution of the present invention, the C6-C30 arylene group is selected from phenylene, biphenylene, terphenylene, naphthylene, anthrylene, phenanthrenyl, fluorenylene, benzofluorenylene, dibenzofluorenylene, naphthofluorenylene, pyrenylene, perylene, spirofluorenylene, triphenylene, fluoranthenylene, hydrogenated benzanthrylene, naphthofluorenylene, tetraphenylmethane or any one or a combination of at least two of benzonaphthofluorenyl.

[0021] As a preferred technical solution of the present invention, the C6-C20 heteroaryl group is selected from any one of a carbazolyl group, a dibenzothiophenyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group or a carbazolyl group.

[0022] As a preferred technical solution of the present invention, the C6-C30 aryl group is selected from any one or a combination of at least two of phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthacenyl, pyrenyl, peryl, spirofluorenyl, triphenylene, fluoranthenyl, hydrogenated benzoanthryl, indenofluorenyl, benzoindenofluorenyl, dibenzoindenofluorenyl, naphthacenyl, tetraphenylmethane or benzonaphthofluorenyl.

[0023] As a preferred technical solution of the present invention, the C6-C20 heteroaryl group is selected from any one of carbazolyl, dibenzothiophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, dinaphthofuranyl, dinaphthothiophenyl or carbazolyl.

[0024] As a preferred technical solution of the present invention, the C6-C40 aryl group is selected from any one or a combination of at least two of phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthacenyl, pyrenyl, peryl, spirofluorenyl, triphenylene, fluoranthenyl, hydrogenated benzoanthryl, indenofluorenyl, benzoindenofluorenyl, dibenzoindenofluorenyl, naphthacenyl, tetraphenylmethane or benzonaphthofluorenyl.

[0025] As a preferred technical solution of the present invention, the C6-C30 heteroaryl group is selected from any one of carbazolyl, dibenzothiophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, dinaphthofuranyl, dinaphthothiophenyl or carbazolyl.

[0026] As a preferred technical solution of the present invention, the C1-C12 alkyl group is selected from any one of methyl, ethyl, propyl, n-butyl, tert-butyl, cyclopentyl, cyclohexyl, octyl and adamantyl.

[0027] As a preferred technical solution of the present invention, the C6-C20 aryl group is selected from any one of phenyl, naphthyl, biphenyl, anthracenyl, phenanthrenyl, fluorenyl, triphenylene or fluoranthenyl.

[0028] As a preferred technical solution of the present invention, the C6-C20 heteroaryl group is selected from any one of a carbazolyl group, a dibenzothiophenyl group, a dinaphthofuranyl group or a carbazolyl group.

[0029] As a preferred technical solution of the present invention, the C1-C6 alkyl group is selected from any one of methyl, ethyl, propyl, n-butyl, tert-butyl, cyclopentyl or cyclohexyl.

[0030] As a preferred technical solution of the present invention, the C1-C6 alkoxy group is selected from any one of methoxy, ethoxy, propoxy, butoxy, pentyloxy or hexyloxy.

[0031] As a preferred technical solution of the present invention, the Ar 11Any one or a combination of at least two selected from the group consisting of a single bond, a phenylene group, a naphthylene group, a triphenylene group, a fluoranthenylene group, a fluorenylene group, an anthrylene group, a phenanthrenyl group, a biphenylene group, a dibenzofuranyl group, and a dibenzothiophenylene group.

[0032] Preferably, the Ar 11 Any one selected from a single bond, phenylene, naphthylene, triphenylene, fluoranthenylene, fluorenylene, anthracenylene, biphenylene, dibenzofuranylene, and dibenzothiophenylene.

[0033] Preferably, the Ar 11 Any one selected from a single bond, a phenylene group, a naphthyl group, a biphenylene group, a dibenzofuranyl group, and a carbazolylene group.

[0034] Preferably, the Ar 11 Any one selected from a single bond, a phenylene group, a naphthylene group, and a biphenylene group. As a preferred technical solution of the present invention, the R 101 Any one or a combination of at least two selected from H, cyano, phenyl, naphthyl, triphenylene, fluoranthenyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

[0035] Preferably, the R 101 Any one or a combination of at least two selected from phenyl, naphthyl, biphenyl, triphenylene, fluoranthenyl, anthracenyl, phenanthryl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothienyl or carbazolyl. As a preferred technical solution of the present invention, R1, R2, and R3 are each independently selected from any one or a combination of at least two selected from methyl, ethyl, propyl, butyl, pentyl, hexyl, H, cyano, phenyl, naphthyl, triphenylene, fluoranthenyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, dibenzofuranyl, dibenzothienyl or carbazolyl.

[0036] Preferably, R1, R2, and R3 are each independently selected from any one of H, methyl, ethyl, propyl, tert-butyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, and carbazolyl, or a combination of at least two thereof.

[0037] Preferably, the hydrogen atoms in the quinoxaline compound can be independently substituted by at least one of -D, -CN, -F, phenyl, naphthyl, triphenylene, fluoranthene, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, triphenylsilyl or triphenylmethyl.

[0038] Preferably, the hydrogen atoms in the quinoxaline compound can be independently substituted by at least one of -D, -CN, -F, methyl, ethyl, tert-butyl, methoxy, phenyl, naphthyl, biphenyl, triphenylsilyl, and triphenylmethyl.

[0039] As a preferred technical solution of the present invention, the quinoxaline compound is selected from any one of the following compounds:

[0040]

[0041]

[0042]

[0043] The substitution means that the hydrogen atoms in the above-mentioned quinoxaline compounds can be independently replaced by deuterium atoms.

[0044] Preferably, the quinoxaline compound is selected from any one of the following compounds:

[0045]

[0046]

[0047]

[0048] It should be noted that the present invention does not have any special restrictions on the preparation method of the above-mentioned triphenylene compounds, and the preparation methods commonly used in the art are applicable. The preparation method of the compound of formula I provided by the present invention is illustrated by way of example:

[0049]

[0050] Wherein, X and Y are each independently selected from any one of fluorine, chlorine, bromine and iodine;

[0051] Ar 11 , R1, R2, R 101 Has the same definition as above.

[0052] In a second aspect, the present invention provides an intermediate, comprising the following compound having a structure shown in Formula M1:

[0053]

[0054] Wherein, X is selected from any one of fluorine, chlorine, bromine and iodine;

[0055] Ar 11 、R 101 Has the same definition as above;

[0056] The intermediate is used to prepare the quinoxaline compound as described in the first aspect.

[0057] Preferably, the intermediate includes the following compounds:

[0058]

[0059] In a third aspect, the present invention provides an organic electroluminescent device, comprising an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode;

[0060] The organic thin film layer material includes the quinoxaline compound as described in the first aspect.

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

[0062] Preferably, the light-emitting layer is a phosphorescent light-emitting layer.

[0063] Preferably, the light-emitting layer is a red phosphorescent light-emitting layer.

[0064] In the present invention, the structure of the quinoxaline compound is designed to make it suitable as the main material of the light-emitting layer of the organic electroluminescent device, so that the organic electroluminescent device has a lower driving voltage, higher current efficiency and longer life. DETAILED DESCRIPTION

[0065] For the convenience of understanding the present invention, the present invention is given below with examples. It should be understood by those skilled in the art that the examples are only for the purpose of helping to understand the present invention and should not be regarded as specific limitations of the present invention.

[0066] Synthesis Example 1

[0067] This synthesis example provides compound P1, and its synthesis method is as follows:

[0068]

[0069] (1) Synthesis of intermediate P1-1

[0070] Under nitrogen protection, 60 mL of dioxane was added to a 250 mL three-necked flask in sequence, followed by 2.4 g of compound M1-0, 3.9 g of compound M1-1, 2.12 g (0.02 mol) of sodium carbonate and 0.23 g (0.0002 mol) of tetrakistriphenylphosphine palladium. The temperature was slowly raised to 40 ° C. for reaction for 2 hours, then raised to 60 ° C. for reaction for 4 hours, then raised to reflux for reaction for 2 hours, cooled to room temperature, added with water and dichloromethane for separation, the organic layer was washed with water, dried with magnesium sulfate, the desiccant was removed, concentrated to dryness, and crystallized from toluene to obtain 2.6 g of intermediate P1-1.

[0071] The obtained intermediate P1-1 was subjected to mass spectrometry detection, and the mass-to-charge ratio (m / z) was measured to be 466.12.

[0072] (2) Synthesis of compound P1

[0073] Under a nitrogen atmosphere, 100 mL of dry xylene, 4.7 g of intermediate P1-1, 1.9 g of carbazole, Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 g), a 10% mass percentage of tri-tert-butylphosphine toluene solution (the mass of tri-tert-butylphosphine solution is 0.8 g) and 1.2 g of sodium tert-butoxide were added to a 250 mL three-necked flask. The mixture was heated to reflux temperature and reacted for 8 h. The mixture was cooled to room temperature and separated by adding water. The organic layer was then washed with water until neutral, dried over magnesium sulfate, filtered to remove the magnesium sulfate, concentrated to dryness, and crystallized from a mixed solvent of toluene and ethanol to obtain 4.7 g of compound P1.

[0074] Compound P1 was detected by mass spectrometry: the mass-to-charge ratio (m / z) was measured to be 597.22.

[0075] Synthesis Examples 2-8

[0076] Synthesis Examples 2-8 respectively provide a compound, the specific structure of the compound is shown in Table 1 below, and the synthesis method of the compound refers to the synthesis method in Synthesis Example 1. The intermediate is first synthesized using raw material 1 (chloride or bromide) and M1-1, and the mass spectrum of the intermediate is measured, and the mass-to-charge ratio (m / z) is recorded. The intermediate is then reacted with raw material 2 to prepare a compound, and the obtained compound is subjected to mass spectrometry detection. The measured mass-to-charge ratio (m / z) is shown in Table 1 below.

[0077] Table 1

[0078]

[0079]

[0080] Synthesis Example 9

[0081] This synthesis example provides compound P21, and its synthesis method is as follows:

[0082]

[0083] Under a nitrogen atmosphere, 120 mL of toluene was added to a 500 mL three-necked flask, followed by the addition of 4.6 g of intermediate P1-1, 3.0 g of intermediate 9-phenylcarbazole-3-boric acid, 2.12 g of sodium carbonate, and 0.1 g of dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium (II) (CAS No. 887919-35-9). The temperature was slowly raised to reflux for 8 hours, then cooled to room temperature, and the mixture was separated by adding water. The organic layer was washed with water and dried over magnesium sulfate. After removing the desiccant, the mixture was concentrated to dryness and separated by silica gel column chromatography with petroleum ether:ethyl acetate = 10:0.5 (volume ratio) to obtain compound P21 (6.0 g).

[0084] The obtained compound P21 was subjected to mass spectrometry detection, and the mass-to-charge ratio (m / z) was measured to be 673.25.

[0085] Other compounds for which the specific synthesis methods are not listed can be synthesized by referring to the above examples in combination with common knowledge in the art.

[0086] The present invention also provides compound D2, the synthesis method of which is as follows:

[0087]

[0088] Compound D2 was synthesized by referring to the synthesis method of compound P1 in Synthesis Example 1. Compound D2 was subjected to mass spectrometry: the mass-to-charge ratio (m / z) was measured to be 597.22.

[0089] The specific structures of some of the compounds used in the following application examples and comparative application examples of the present invention are as follows:

[0090]

[0091]

[0092] Application Example 1

[0093] This application example provides a red organic electroluminescent device, using the compound provided by the present invention as a main material of the light-emitting layer. The structure of the red organic electroluminescent device is:

[0094] ITO / HT-1: HI-2[5%](80nm) / HT-1(30nm) / EB-1(20nm) / host material: PRD-1[5%](35nm) / ETL-1(25nm) / LiF(0.5nm) / Al(150nm).

[0095] The preparation method of the red organic electroluminescent device is as follows:

[0096] The material was placed in a vacuum chamber and evacuated to 1×10 -5 ~1×10 -6 Pa was vacuum evaporated onto the cleaned ITO substrate to prepare OLED devices.

[0097] PRD-1[5%] refers to the dye doping ratio, meaning the volume ratio of the host material to the dye PRD-1 is 95:5. HT-1:HI-2[5%] refers to the p-type dopant ratio, meaning the volume ratio of the hole-transporting material HT-1 to the p-type dopant HI-2 is 95:5. HT-1 is a hole-transporting material; HT-1:HI-2[5%] serves as the hole-injection layer, and EB-1 is the electron-blocking layer.

[0098] The main material of the light-emitting layer of the red organic electroluminescent device provided in this application example is compound P1.

[0099] Application Example 2-17, Comparative Application Example 1-4

[0100] Application Examples 2-17 and Comparative Application Examples 1-4 respectively provide a red organic electroluminescent device. The only difference from Application Example 1 is that the main material of the light-emitting layer is replaced with other compounds (see Table 2 below for details). The other preparation steps and conditions are the same as those of Application Example 1.

[0101] Performance Testing

[0102] The brightness, driving voltage, current efficiency and LT95 of the organic electroluminescent device provided above were tested, wherein the current efficiency is the brightness of 1000cd / m 2 The corresponding value, LT95, refers to maintaining the initial current density of the device at 10mA / cm 2 The time required for the device efficiency to drop to 95% of the efficiency corresponding to the initial current density remains unchanged. The driving voltage, current efficiency and LT95 are relative values. The specific test results are shown in Table 2 below:

[0103] Table 2

[0104] Main material <![CDATA[Brightness / (cd / m 2 )]]> Driving voltage Current efficiency LT95 Application Example 1 P1 1000 0.68 1.17 1.02 Application Example 2 P2 1000 0.69 0.99 1.06 Application Example 3 P3 1000 0.72 0.98 1.37 Application Example 4 P4 1000 0.66 1.69 1.46 Application Example 5 P5 1000 0.80 1.79 1.46 Application Example 6 P6 1000 0.90 2.05 1.41 Application Example 7 P7 1000 0.80 1.07 1.57 Application Example 8 P8 1000 0.62 2.91 1.35 Application Example 9 P10 1000 0.86 0.79 1.20 Application Example 10 P12 1000 0.78 1.03 1.37 Application Example 11 P13 1000 0.96 0.90 1.37 Application Example 12 P15 1000 0.60 0.82 1.06 Application Example 13 P17 1000 0.60 1.12 1.46 Application Example 14 P18 1000 0.76 1.07 3.29 Application Example 15 P19 1000 0.97 1.22 1.41 Application Example 16 P20 1000 0.87 1.22 3.37 Application Example 17 P21 1000 1.09 1.55 2.00 Comparative Application Example 1 D1 1000 1.11 0.88 0.81 Comparative Application Example 2 D2 1000 1 1 1

[0105] It can be seen from Application Examples 4-6 and Application Example 8 that when R 101 When the carbazole group is included, the compound is used as the main material of the OLED device, and the OLED device prepared has high current efficiency.

[0106] It can be seen from Application Examples 14 and 16 that Ar in the compound of Formula I and the compound of Formula II 11When the carbazole group is included, the compound is used as the main material of the OLED device, and the prepared OLED device has a longer service life.

[0107] As can be seen from Application Examples 1-16 and Comparative Application Examples 1-2, the present invention designs the structure of quinoxaline compounds to make them suitable as the main material of the light-emitting layer of organic electroluminescent devices, so that the organic electroluminescent devices have lower driving voltage, higher current efficiency and longer life.

[0108] In summary, the present invention designs the structure of quinoxaline compounds to make them suitable as the host material of the light-emitting layer of an organic electroluminescent device, so that the organic electroluminescent device has better comprehensive performance.

[0109] The applicant declares that the present invention uses the above-described embodiments to illustrate the detailed process flow of the present invention, but the present invention is not limited to the above-described detailed process flow, that is, it does not mean that the present invention must rely on the above-described detailed process flow to be implemented. Those skilled in the art should understand that any improvements to the present invention, equivalent replacements for various raw materials in the products of the present invention, addition of auxiliary ingredients, and selection of specific methods, etc., are all within the scope of protection and disclosure of the present invention.

Claims

1. A quinoxaline compound, characterized in that The quinoxaline compound has a structure shown in the following formula I or formula II: Ar 11 Any one selected from a single bond, a C6-C30 arylene group or a C6-C20 heteroarylene group; R 101 Any one selected from H, cyano, C6-C30 aryl or C6-C20 heteroaryl; R1, R2, and R3 are each independently selected from any one of H, C6-C40 aryl, C6-C30 heteroaryl, or C1-C12 alkyl; The hydrogen atoms in the quinoxaline compound can each independently be substituted by at least one of a deuterium atom, -CN, -F, a C6-C20 aryl group, a C6-C20 heteroaryl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a triphenylsilyl group or a triphenylmethyl group.

2. The quinoxaline compound according to claim 1, wherein The C6-C30 arylene group is selected from any one or a combination of at least two of phenylene, biphenylene, terphenylene, naphthylene, anthrylene, phenanthrenyl, fluorenylene, benzofluorenylene, dibenzofluorenylene, naphthofluorenylene, pyrenylene, perylene, spirofluorenylene, triphenylene, fluoranthenylene, hydrobenzoanthrylene, naphthylene fluorenylene, tetraphenylmethane or benzonaphthofluorenylene; Preferably, the C6-C20 heteroarylene group is selected from any one of a carbazolylene group, a dibenzothiophenylene group, a naphthobenzofuranyl group, a naphthobenzothiophenylene group, a dinaphthofuranyl group, a dinaphthothiophenylene group or a carbazolylene group; Preferably, the C6-C30 aryl group is selected from any one or a combination of at least two of phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthrofluorenyl, pyrenyl, peryl, spirofluorenyl, triphenylene, fluoranthenyl, hydrogenated benzanthryl, indenofluorenyl, benzoindenofluorenyl, dibenzoindenofluorenyl, naphthrofluorenyl, tetraphenylmethane or benzonaphthofluorenyl; Preferably, the C6-C20 heteroaryl group is selected from any one of carbazolyl, dibenzothiophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, dinaphthofuranyl, dinaphthothiophenyl or carbazolyl; Preferably, the C6-C40 aryl group is selected from any one or a combination of at least two of phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthrofluorenyl, pyrenyl, peryl, spirofluorenyl, triphenylene, fluoranthenyl, hydrogenated benzanthryl, indenofluorenyl, benzoindenofluorenyl, dibenzoindenofluorenyl, naphthrofluorenyl, tetraphenylmethane or benzonaphthofluorenyl; Preferably, the C6-C30 heteroaryl group is selected from any one of carbazolyl, dibenzothiophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, dinaphthofuranyl, dinaphthothiophenyl or carbazolyl; Preferably, the C1-C12 alkyl group is selected from any one of methyl, ethyl, propyl, n-butyl, tert-butyl, cyclopentyl, cyclohexyl, octyl and adamantyl; Preferably, the C6-C20 aryl group is selected from any one of phenyl, naphthyl, biphenyl, anthracenyl, phenanthrenyl, fluorenyl, triphenylene or fluoranthenyl; Preferably, the C6-C20 heteroaryl group is selected from any one of carbazolyl, dibenzothiophenyl, dinaphthofuranyl or carbazolyl; Preferably, the C1-C6 alkyl group is selected from any one of methyl, ethyl, propyl, n-butyl, tert-butyl, cyclopentyl or cyclohexyl; Preferably, the C1-C6 alkoxy group is selected from any one of methoxy, ethoxy, propoxy, butoxy, pentyloxy or hexyloxy.

3. The quinoxaline compound according to claim 1 or 2, characterized in that The Ar 11 Any one or a combination of at least two selected from the group consisting of a single bond, a phenylene group, a naphthylene group, a triphenylene group, a fluoranthenylene group, a fluorenylene group, an anthrylene group, a phenanthrenyl group, a biphenylene group, a dibenzofuranyl group, and a dibenzothiophenylene group; Preferably, the Ar 11 Any one selected from a single bond, phenylene, naphthylene, triphenylene, fluoranthenylene, fluorenylene, anthracenylene, biphenylene, dibenzofuranylene, and dibenzothiophenylene; Preferably, the Ar 11 Any one selected from a single bond, phenylene, naphthyl, biphenylene, dibenzofuranyl, and carbazolyl; Preferably, the Ar 11 Any one selected from a single bond, a phenylene group, a naphthylene group, and a biphenylene group; preferably, the R 101 Any one or a combination of at least two selected from H, cyano, phenyl, naphthyl, triphenylene, fluoranthene, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl; Preferably, the R 101 Any one or a combination of at least two selected from phenyl, naphthyl, biphenyl, triphenylene, fluoranthenyl, anthracenyl, phenanthryl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl; preferably, R1, R2, and R3 are each independently selected from any one or a combination of at least two selected from methyl, ethyl, propyl, butyl, pentyl, hexyl, H, cyano, phenyl, naphthyl, triphenylene, fluoranthenyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl; Preferably, R1, R2, and R3 are each independently selected from any one of H, methyl, ethyl, propyl, tert-butyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, and carbazolyl, or a combination of at least two thereof.

4. The quinoxaline compound according to any one of claims 1 to 3, characterized in that The hydrogen atoms in the quinoxaline compound can each independently be substituted by at least one of -D, -CN, -F, phenyl, naphthyl, triphenylene, fluoranthenyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, triphenylsilyl or triphenylmethyl; Preferably, the hydrogen atoms in the quinoxaline compound can be independently substituted by at least one of -D, -CN, -F, methyl, ethyl, tert-butyl, methoxy, phenyl, naphthyl, biphenyl, triphenylsilyl, and triphenylmethyl.

5. The quinoxaline compound according to any one of claims 1 to 4, characterized in that The quinoxaline compound is selected from any one of the following compounds: The substitution means that the hydrogen atoms in the above-mentioned quinoxaline compounds can be independently replaced by deuterium atoms.

6. The quinoxaline compound according to any one of claims 1 to 5, characterized in that The quinoxaline compound is selected from any one of the following compounds:

7. An intermediate, characterized in that The intermediates include the following compounds having the structure shown in formula M1: Wherein, X is selected from any one of fluorine, chlorine, bromine and iodine; Ar 11 、R 101 has the same definition as in claim 1; The intermediate is used to prepare the quinoxaline compound according to any one of claims 1 to 6.

8. The intermediate according to claim 7, characterized in that The intermediates include the following compounds:

9. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises an anode, a cathode and an organic thin film layer arranged between the anode and the cathode; The organic thin film layer material includes the quinoxaline compound according to any one of claims 1 to 6.

10. The organic electroluminescent device according to claim 9, characterized in that: The organic thin film layer includes a light-emitting layer, and a main material of the light-emitting layer includes the quinoxaline compound according to any one of claims 1 to 6.

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