A benzanthracene compound containing pyrene, an intermediate and an organic electroluminescent device

Abstract

This invention provides a pyrene-containing benzanthracene compound, an intermediate, and an organic electroluminescent device, relating to the field of organic electroluminescent materials technology. By designing the structure of the compound, this invention enables it to serve as the main material for the light-emitting layer of an OLED device, resulting in OLED devices exhibiting lower driving voltage, higher current efficiency, and longer lifetime.

Description

Technical Field

[0001] This invention belongs to the field of organic optoelectronic technology, specifically relating to a pyrene-containing benzanthracene compound, an intermediate, and an organic electroluminescent device. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are devices fabricated by depositing one or more layers of organic material between two metal electrodes via spin coating or vacuum evaporation. A classic three-layer OLED comprises a hole transport layer, an emissive layer, and an electron transport layer. Holes generated by the anode combine with electrons generated by the cathode via the electron transport layer in the emissive layer to form excitons, which then emit light. OLEDs can be tuned to emit various desired light colors by changing the material of the emissive layer.

[0003] Organic electroluminescent devices, as a novel display technology, possess unique advantages such as self-illumination, wide viewing angle, low energy consumption, high efficiency, thinness, rich colors, fast response speed, wide applicable temperature range, low driving voltage, the ability to manufacture flexible, bendable, and transparent display panels, and environmental friendliness. They can be applied to flat panel displays and next-generation lighting, and can also be used as backlights for LCDs.

[0004] Since their invention in the late 1980s, organic light-emitting diodes (OLEDs) have been used in various industries, such as as screens in cameras and mobile phones. However, current OLED devices suffer from low efficiency and short lifespan, limiting their wider application, especially in large-screen displays. Therefore, it is necessary to improve the efficiency and lifespan of these devices. A key factor limiting the performance of OLED devices is the performance of the organic light-emitting materials used in them. Therefore, it is essential to develop stable and efficient organic light-emitting materials to improve the current efficiency and lifespan of OLED devices. Summary of the Invention

[0005] To address the shortcomings of existing technologies, the present invention aims to provide a pyrene-containing benzanthracene compound, an intermediate, and an organic electroluminescent device. The present invention designs the structure of the compound to serve as the main material for the light-emitting layer of an OLED light-emitting device, resulting in an OLED light-emitting device with lower driving voltage, higher current efficiency, and longer lifespan.

[0006] To achieve this objective, the present invention adopts the following technical solution:

[0007] In a first aspect, the present invention provides a pyrene-containing benzanthracene compound having the structure shown in Formula I:

[0008]

[0009] Formula I;

[0010] R1 and R2 are each independently selected from any one of phenyl, naphthyl, biphenyl, terphenyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, naphthobenzofuranyl, and N-phenylcarbazoyl.

[0011] L is selected from any one of single bond, phenylene, naphthylene, and biphenylene;

[0012] In compounds of Formula I, each hydrogen atom can be independently replaced by any one of the following: deuterium atom, cyano group, C1-C12 straight-chain or branched alkyl group, C3-C12 cycloalkyl group, C1-C12 straight-chain or branched alkoxy group, C3-C12 cycloalkoxy group, phenyl group, naphthyl group, biphenyl group, or terphenyl group.

[0013] This invention designs the structure of compounds to obtain pyrene-containing benzanthracene compounds that can be used as the main material for the light-emitting layer of OLED light-emitting devices, enabling OLED light-emitting devices to have lower driving voltage, higher current efficiency and longer lifespan.

[0014] In this invention, "D" represents a deuterium atom, and the same applies below.

[0015] Preferably, R1 and R2 are the same.

[0016] Preferably, R1 and R2 are N-phenylcarbazole groups. In this invention, when both R1 and R2 are N-phenylcarbazole groups, the current efficiency of the device can be significantly improved.

[0017] Preferably, the C1-C12 straight-chain or branched alkyl group is selected from any one of methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, pentyl, octyl, undecyl or dodecyl, and more preferably any one of methyl, ethyl, propyl, n-butyl, tert-butyl or pentyl.

[0018] Preferably, the C3-C12 cycloalkyl group is selected from any one of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or adamantyl, and more preferably cyclohexyl.

[0019] Preferably, the C1-C12 straight-chain or branched alkoxy groups are selected from any one of methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, or nonoxy.

[0020] Preferably, the C3~C12 cycloalkoxy group is selected from any one of cyclopropoxy, cyclobutoxy, cyclopentoxy, or cyclohexyloxy.

[0021] Preferably, each hydrogen atom in the compound of formula I can be independently replaced by any one of deuterium, cyano, methyl, phenyl, naphthyl, or biphenyl.

[0022] Preferably, the pyrene-containing benzanthracene compound has the structure shown in Formulas I-1 to I-3:

[0023] ;

[0024] In Equations I-1 to I-3, R1, R2, and L have the same range of limitation as in Equation I;

[0025] In the compounds of formulas I-1 to I-3, the hydrogen atoms can be independently replaced by any one of the following: deuterium atom, cyano group, C1-C12 straight-chain or branched alkyl group, C3-C12 cycloalkyl group, C1-C12 straight-chain or branched alkoxy group, C3-C12 cycloalkoxy group, phenyl group, naphthyl group, biphenyl group, and terphenyl group.

[0026] Preferably, the pyrene-containing benzanthracene compound is selected from any one of the following substituted or unsubstituted compounds:

[0027]

[0028]

[0029] ;

[0030] The substitution refers to the replacement of at least one hydrogen atom in the above compound with a deuterium atom.

[0031] Preferably, the pyrene-containing benzanthracene compound is selected from any one of the following substituted or unsubstituted compounds 1 to 11:

[0032] , , , , , , , , , , ;

[0033] The substitution refers to the replacement of at least one hydrogen atom in compounds 1 to 11 by a deuterium atom.

[0034] It should be noted that the present invention does not impose any special limitations on the synthesis method of the pyrene-containing benzanthracene compounds shown in Formula I, and commonly used synthesis methods in the art are applicable.

[0035] Secondly, the present invention provides an intermediate having a structure as shown in formula MA or formula MC:

[0036] , ;

[0037] In formula MA, X2 and X3 are each independently selected from F, Cl, Br or I, and L has the same limiting range as in formula I;

[0038] In formula MC, X1, X2, and X3 are each independently selected from F, Cl, Br, or I;

[0039] The hydrogen atoms in formula MA and formula MC can be independently replaced by any one of the following: deuterium atom, cyano group, C1~C12 straight-chain or branched alkyl group, C3~C12 cycloalkyl group, C1~C12 straight-chain or branched alkoxy group, C3~C12 cycloalkoxy group, phenyl group, naphthyl group, biphenyl group, and terphenyl group;

[0040] The intermediate is used to prepare pyrene-containing benzanthracene compounds as described in the first aspect.

[0041] Preferably, the intermediate is selected from the following structures:

[0042] , , , , .

[0043] The synthetic methods of formulas MA and MC, and their applications in the preparation of compounds of formula I, are illustrated below (using the same R1 and R2 as an example):

[0044]

[0045] ;

[0046] Wherein, R1 is selected from any one of phenyl, naphthyl, biphenyl, terphenyl, fluoranyl, fluorenyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, naphthobenzofuranyl, and carbazoleyl;

[0047] L is defined as above;

[0048] Among them, X1, X2, and X3 are independently selected from F, Cl, Br, or I;

[0049] The hydrogen atoms in each of the above raw materials and intermediates can be independently replaced by any one of the following: deuterium atom, cyano group, C1~C12 straight-chain or branched alkyl group, C3~C12 cycloalkyl group, C1~C12 straight-chain or branched alkoxy group, C3~C12 cycloalkoxy group, phenyl group, naphthyl group, biphenyl group, and terphenyl group.

[0050] Thirdly, the present invention provides an organic electroluminescent device, the organic electroluminescent device comprising an anode, a cathode and an organic thin film layer disposed between the anode and the cathode, the organic thin film layer comprising a pyrene-containing benzene-anthracene compound as described in the first aspect.

[0051] Preferably, the organic thin film layer includes a light-emitting layer, which includes the pyrene-containing benzanthracene compound.

[0052] Preferably, the light-emitting layer comprises a host material and a dopant material, wherein the host material comprises the pyrene-containing benzanthracene compound.

[0053] Preferably, the doped material comprises at least one of a compound having the structure shown in Formula II and a compound having the structure shown in Formula III:

[0054]

[0055] Mode ;

[0056]

[0057] Mode ;

[0058] Mode in Ar 21 Ar 22 Each is independently selected from any one of substituted or unsubstituted C6~C20 (e.g., C6, C8, C10, C12, C16 or C20) aryl, substituted or unsubstituted C3~C20 (e.g., C3, C6, C8, C10, C12, C16 or C20) heteroaryl;

[0059] R 21 R 22 and R 23 Each is independently selected from any one of hydrogen, C1-C12 (e.g., C1, C2, C4, C6, C8, C10, or C12) straight-chain or branched alkyl groups, and C6-C12 (e.g., C6, C8, C10, or C12) cycloalkyl groups;

[0060] Ar 21 Ar 22 The substituents described herein are each independently selected from C1-C5 straight-chain or branched alkyl groups (e.g., methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl) or C6-C12 aryl groups (e.g., phenyl, diphenyl, naphthyl).

[0061] Mode in Ar 31 Ar32 Ar 33 and Ar 34 Each is independently selected from any one of substituted or unsubstituted C6~C22 (e.g., C6, C8, C10, C16, C18 or C22) aryl, substituted or unsubstituted C12~C40 (e.g., C12, C18, C20, C24, C30, C36 or C40) heteroaryl;

[0062] R 31 Selected from any one of phenyl, naphthyl, or biphenyl;

[0063] a is selected from 0 or 1;

[0064] Ar 31 Ar 32 Ar 33 Ar 34 The substituents described herein are each independently selected from C1-C5 straight-chain or branched alkyl groups (e.g., methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl) or C6-C12 (e.g., C6, C8, C10, or C12) aryl groups.

[0065] Preferably, formula In the middle, the Ar 21 Ar 22 Each independently selected , , , , , , , , , , , , , , , , Any of the following, with dashed lines representing connection points.

[0066] Preferably, formula In, the R 21 R 22 and R 23 Each is independently selected from any one of hydrogen, methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl, or adamantyl.

[0067] Preferably, formula In the middle, the Ar 31 Ar 32 Ar 33 and Ar34 Each independently selected , , , , , , , , , Any one or at least two of the above, with dashed lines indicating connection sites.

[0068] Preferably, the formula The compound is selected from any one of the following compounds:

[0069] .

[0070] Preferably, the formula The compound is selected from any one of the following compounds:

[0071] .

[0072] Preferably, the light-emitting layer includes a first light-emitting layer and a second light-emitting layer, wherein the first light-emitting layer includes a first host material and a first dopant material, and the second light-emitting layer includes a second host material and a second dopant material;

[0073] The first host material comprises the pyrene-containing benzanthracene compound, and the second host material comprises a compound having the structure shown in Formula IV:

[0074]

[0075] Formula IV;

[0076] In Formula IV, the Ar 11 Ar 12 Each is independently selected from any one of substituted or unsubstituted C6-C40 aryl groups or substituted or unsubstituted C12-C40 heteroaryl groups;

[0077] The R 11 R 12 Each is independently selected from any one of substituted or unsubstituted C1-C6 straight-chain or branched alkyl groups, substituted or unsubstituted C6-C40 aryl groups, or substituted or unsubstituted C12-C40 heteroaryl groups;

[0078] Ar 11 Ar 12 R11 R 12 In this context, each of the substituents is independently selected from at least one of C1-C6 straight-chain or branched alkyl, C6-C20 aryl, and C6-C20 heteroaryl;

[0079] The m and n are each independently selected from integers from 0 to 4, for example, they can be 0, 1, 2, 3, 4;

[0080] In the compound shown in Formula IV, each H atom can be independently replaced by a D atom;

[0081] Preferably, the first doping material and the second doping material are the same or different, including at least one of compounds having the structure shown in Formula II and compounds having the structure shown in Formula III.

[0082] Preferably, in formula IV, the Ar 11 Ar 12 Each independently selected , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , Any one of them.

[0083] Preferably, in formula IV, the R 11 R 12 Each is independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, , Any one of them.

[0084] Preferably, the compound represented by Formula IV is selected from any one of the following compounds, whether substituted or unsubstituted:

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108] The substitution refers to the replacement of at least one H atom in the above compound with a D atom.

[0109] Preferably, the compound represented by Formula IV is selected from any one of the following compounds:

[0110] .

[0111] Preferably, the volume percentage of the main material in the light-emitting layer is 60% to 99.9% (for example, it can be 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 98% or 99.9%), more preferably 70% to 99.5%, and even more preferably 85% to 95%.

[0112] Preferably, the organic thin film layer further includes one or a combination of several of the following: a hole injection layer, a hole transport layer, an electron transport layer, and an electron injection layer. In this invention, no special limitations are placed on the materials used for the hole injection layer, hole transport layer, electron transport layer, and electron injection layer; any materials known in the art capable of hole injection, hole transport, electron transport, and electron injection can be used.

[0113] Fourthly, the present invention provides a display device comprising the organic electroluminescent device as described in the third aspect.

[0114] Compared with the prior art, the present invention has the following beneficial effects:

[0115] This invention designs the structure of compounds to obtain pyrene-containing benzene-anthracene compounds as the main material for the light-emitting layer of OLED devices, thereby enabling OLED devices to have lower driving voltage, higher current efficiency and longer lifespan. Detailed Implementation

[0116] To facilitate understanding of the present invention, the following embodiments are provided. Those skilled in the art should understand that these embodiments are merely illustrative and should not be construed as limiting the scope of the invention.

[0117] Preparation Example 1: Synthesis of Intermediate 1-1

[0118]

[0119] In a three-necked flask, add 19 g of intermediate 2-0, 300 mL of glacial acetic acid, 30 mL of 1,2-dichloroethane, 14 g of elemental iodine, and 0.2 g of iron powder. Heat in an oil bath at 80°C for 12 hours. Cool down, add water and 1,2-dichloroethane, filter, and separate the layers. Wash the organic layer sequentially with water, 2% sodium bicarbonate solution, saturated sodium bisulfite solution, and water. Then concentrate the organic layer to dryness, separate by silica gel column chromatography, and elute with petroleum ether to obtain 12.6 g of intermediate 1-0.

[0120] The mass spectra of intermediate 1-0 were measured, m / z: 509.81.

[0121] The NMR spectra of intermediate 1-0 were measured and the data are as follows: 1H-NMR (Bruker, Switzerland, Avance II 400MHz NMR spectrometer, CDCl3), δ8.92 (m, 1H), δ8.14~8.03 (m, 3H), 7.71 (m, 1H), δ7.61~7.50 (m, 4H).

[0122] Under nitrogen protection, 100 mL of toluene, 30 mL of n-butanol, and 20 mL of water were added sequentially to a three-necked flask. Then, 5.1 g of intermediate 1-0, 2.7 g of pyrene-1-boric acid, 2.12 g of sodium carbonate, and 0.23 g of tetrakis(triphenylphosphine)palladium were added. The mixture was slowly heated to 50 °C and reacted for 2 h, then heated to 70 °C and reacted for 8 h. The mixture was cooled to room temperature, and water was added to dissolve the organic layer. The organic layer was washed with water and dried with magnesium sulfate. After removing the desiccant, the mixture was concentrated to dryness and crystallized with toluene to obtain 3.8 g of intermediate 1-1.

[0123] The obtained intermediate 1-1 was subjected to mass spectrometry analysis, and the mass-to-charge ratio (m / z) was measured to be 583.98.

[0124] Preparation Examples 2-4

[0125] Preparation Examples 2-4 provide intermediates and their synthesis methods, respectively. The synthesis methods are the same as those for intermediate 1-1 provided in Preparation Example 1. The mass spectra of the prepared intermediates were tested, as detailed in Table 1 below.

[0126] Table 1

[0127]

[0128]

[0129] Synthesis Example 1

[0130] This synthetic example provides compound 1 and its synthetic method, which is as follows:

[0131]

[0132] Under nitrogen protection, 120 mL of toluene, 40 mL of n-butanol, and 25 mL of water were added sequentially to a three-necked flask. Then, 2.9 g of intermediate 1-1, 1.5 g of phenylboronic acid, 2.12 g of sodium carbonate, and 0.23 g of tetraphenylphosphine palladium were added. The mixture was slowly heated to reflux and reacted for 8 hours. Water was added to separate the contents. The organic layer was washed with water and dried with magnesium sulfate. After removing the desiccant, the mixture was concentrated to dryness and crystallized with toluene to obtain 1.6 g of compound 1.

[0133] The mass-to-charge ratio (m / z) of compound 1 was measured to be 580.22 by mass spectrometry.

[0134] Synthesis Examples 2-6

[0135] Synthesis Examples 2-6 provide a pyrene-containing benzenexane compound and its synthesis method. The synthesis method of the pyrene-containing benzenexane compound is the same as that of Compound 1 provided in Synthesis Example 1. The mass spectra of the prepared pyrene-containing benzenexane compounds were tested, as detailed in Table 2 below.

[0136] Table 2

[0137]

[0138]

[0139]

[0140] Other compounds for which specific synthetic steps are not listed can be prepared using common knowledge in the field, combined with the above synthetic examples.

[0141] The specific structures of the compounds used in the following application examples and comparative application examples are shown below:

[0142] , , , , , , , , , , , , , , , , , , , , , .

[0143] Application Example 1

[0144] This application example provides an organic electroluminescent device with the following structure: ITO / HTL (80nm) / BH1:BD1 (5%) (10nm) / BH2:BD2 (5%) (20nm) / ETL (30nm) / Al (150nm);

[0145] The fabrication method of the above-mentioned organic electroluminescent device is as follows:

[0146] Each layer of 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.

[0147] HTL (80nm) refers to the hole transport layer, which has a thickness of 80nm.

[0148] BH1:BD1 (5%) (10nm) refers to the first emitting layer, BH1 refers to the first blue light host material, BD1 refers to the first doping material, and BH1:BD1 (5%) means that the volume ratio of the first blue light host material to the first doping material in the first emitting layer is 95:5, and the film thickness of the first emitting layer is 10nm; in this application example, BH1 material is compound 1, and BD1 material is compound BD-2;

[0149] BH2:BD2 (5%) (20nm) refers to the second emitting layer, BH2 refers to the second blue light host material, BD2 refers to the second dopant material, and BH2:BD2 (5%) means that the volume ratio of the second blue light host material to the second dopant material in the second emitting layer is 95:5, and the film thickness of the second emitting layer is 20nm. In this application example, the BH2 material is compound BZ205, and the BD2 material is compound BD-2.

[0150] ETL (30nm) refers to the electron transport layer, which has a film thickness of 30nm.

[0151] ITO refers to the anode, and Al (150nm) refers to the cathode.

[0152] Application Examples 2-3

[0153] Application Examples 2 and 3 provide an organic electroluminescent device, which differs from Application Example 1 only in that the BH1 material in the first light-emitting layer is different (as shown in Table 3 below). The other preparation steps are the same as in Application Example 1.

[0154] Compare and contrast examples 1-4

[0155] Comparative Application Examples 1-4 provide an organic electroluminescent device, which differs from Application Example 1 only in that the BH1 material in the first light-emitting layer is different (as shown in Table 3 below). The other preparation steps are the same as those in Application Example 1.

[0156] The test items include the brightness, driving voltage, current efficiency, and LT80 of the organic electroluminescent device; where LT80 refers to maintaining the device's initial brightness of 1000 cd / m². 2 With the current density remaining constant, the device efficiency drops to the initial luminance of 1000 cd / m². 2 The time required to achieve 80% of the corresponding efficiency. The drive voltage, current efficiency, and LT80 are all relative values ​​(based on Application Example 1).

[0157] The specific test results are shown in Table 3 below:

[0158] Table 3

[0159]

[0160] As can be seen from the above, by designing the structure of the compound, the present invention obtains a pyrene-containing benzene-anthracene compound as the main material of the light-emitting layer of the OLED device, which enables the OLED device to have a lower driving voltage, higher current efficiency and longer lifespan.

[0161] Application Examples 4-7

[0162] Application Examples 4-7 provide an organic electroluminescent device, which differs from Application Example 1 only in that the BH1 material in the first light-emitting layer is different (as shown in Table 4 below). The other preparation steps are the same as in Application Example 1.

[0163] The test items include the brightness, driving voltage, current efficiency, and LT80 of the organic electroluminescent device; where LT80 refers to maintaining the device's initial brightness of 1000 cd / m². 2With the current density remaining constant, the device efficiency drops to the initial luminance of 1000 cd / m². 2 The time required to achieve 80% of the corresponding efficiency. Among them, the drive voltage, current efficiency, and LT80 are all relative values ​​(based on application example 4).

[0164] The specific test results are shown in Table 4 below:

[0165] Table 4

[0166]

[0167] As described above, this invention, through the design of the compound structure, obtains pyrene-containing benzanthracene compounds as the main material for the light-emitting layer of OLED devices, resulting in OLED devices with lower driving voltage, higher current efficiency, and longer lifespan. In particular, when both R1 and R2 are N-phenylcarbazole groups, the current efficiency of the device can be significantly improved.

[0168] Application Examples 8-10

[0169] Application Examples 8-10 provide an organic electroluminescent device, which differs from Application Example 1 only in that the BH1 material in the first light-emitting layer is different (as shown in Table 5 below). In addition, the BD1 material in the first light-emitting layer is replaced by compound BD-3 instead of compound BD-2. The other preparation steps are the same as in Application Example 1.

[0170] The test items include the brightness, driving voltage, current efficiency, and LT80 of the organic electroluminescent device; where LT80 refers to maintaining the device's initial brightness of 1000 cd / m². 2 With the current density remaining constant, the device efficiency drops to the initial luminance of 1000 cd / m². 2 The time required to achieve 80% of the corresponding efficiency. The drive voltage, current efficiency, and LT80 are all relative values ​​(based on Application Example 10).

[0171] The specific test results are shown in Table 5 below:

[0172] Table 5

[0173]

[0174] Application Examples 11-12

[0175] Application Examples 11-12 provide an organic electroluminescent device, which differs from Application Example 1 only in that the BH1 material in the first light-emitting layer is different (as shown in Table 6 below). In addition, the BD1 material in the first light-emitting layer is replaced by compound BD-3 instead of compound BD-2. The other preparation steps are the same as in Application Example 1.

[0176] The test items include the brightness, driving voltage, current efficiency, and LT80 of the organic electroluminescent device; where LT80 refers to maintaining the device's initial brightness of 1000 cd / m². 2 With the current density remaining constant, the device efficiency drops to the initial luminance of 1000 cd / m². 2 The time required to achieve 80% of the corresponding efficiency. The drive voltage, current efficiency, and LT80 are all relative values ​​(based on Application Example 11).

[0177] The specific test results are shown in Table 6 below:

[0178] Table 6

[0179]

[0180] As can be seen from the above, by designing the structure of the compound, the present invention obtains a pyrene-containing benzene-anthracene compound as the main material of the light-emitting layer of the OLED device, which enables the OLED device to have a lower driving voltage, higher current efficiency and longer lifespan.

[0181] The present invention has been illustrated with the above embodiments to describe the detailed process flow of the present invention. However, the present invention is not limited to the above detailed process flow, that is, it does not mean that the present invention must rely on the above detailed process flow to be implemented. Those skilled in the art should understand that any improvements to the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. A pyrene-containing benzanthracene compound, characterized in that, The pyrene-containing benzanthracene compounds have the structure shown in Formula I: Formula I; R1 and R2 are each independently selected from any one of phenyl, naphthyl, biphenyl, terphenyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, naphthobenzofuranyl, and N-phenylcarbazoyl. L is selected from any one of single bond, phenylene, naphthylene, and biphenylene; In compounds of Formula I, each hydrogen atom can be independently replaced by any one of the following: deuterium atom, cyano group, C1-C12 straight-chain or branched alkyl group, C3-C12 cycloalkyl group, C1-C12 straight-chain or branched alkoxy group, C3-C12 cycloalkoxy group, phenyl group, naphthyl group, biphenyl group, or terphenyl group.

2. The pyrene-containing benzanthracene compound according to claim 1, characterized in that, R1 and R2 are the same; Preferably, R1 and R2 are N-phenylcarbazolyl.

3. The pyrene-containing benzanthracene compound according to claim 1, characterized in that, The C1-C12 straight-chain or branched alkyl group is selected from any one of methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, pentyl, octyl, undecyl or dodecyl, and is more preferably any one of methyl, ethyl, propyl, n-butyl, tert-butyl or pentyl; Preferably, the C3-C12 cycloalkyl group is selected from any one of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or adamantyl, and more preferably cyclohexyl; Preferably, the C1-C12 straight-chain or branched alkoxy groups are selected from any one of methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, or nonoxy. Preferably, the C3-C12 cycloalkoxy group is selected from any one of cyclopropoxy, cyclobutoxy, cyclopentoxy, or cyclohexyloxy. Preferably, each hydrogen atom in the compound of formula I can be independently replaced by any one of deuterium, cyano, methyl, phenyl, naphthyl, or biphenyl.

4. The pyrene-containing benzanthracene compound according to claim 1, characterized in that, The pyrene-containing benzanthracene compounds have the structures shown in Formulas I-1 to I-3 as follows: ； In Equations I-1 to I-3, R1, R2, and L have the same range of limitation as in Equation I; In the compounds of formulas I-1 to I-3, the hydrogen atoms can be independently replaced by any one of the following: deuterium atom, cyano group, C1-C12 straight-chain or branched alkyl group, C3-C12 cycloalkyl group, C1-C12 straight-chain or branched alkoxy group, C3-C12 cycloalkoxy group, phenyl group, naphthyl group, biphenyl group, and terphenyl group.

5. The pyrene-containing benzanthracene compound according to claim 1, characterized in that, The pyrene-containing benzanthracene compound is 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; Preferably, the pyrene-containing benzanthracene compound is selected from any one of the following substituted or unsubstituted compounds 1 to 11: 、 、 、 、 、 、 、 、 、 、 ； The substitution refers to the replacement of at least one hydrogen atom in compounds 1 to 11 by a deuterium atom.

6. An intermediate, characterized in that, The intermediate has a structure as shown in formula MA or formula MC: 、 ； In formula MA, X2 and X3 are each independently selected from F, Cl, Br or I, and L has the same limiting range as in formula I; In formula MC, X1, X2, and X3 are each independently selected from F, Cl, Br, or I; The hydrogen atoms in formula MA and formula MC can be independently replaced by any one of the following: deuterium atom, cyano group, C1~C12 straight-chain or branched alkyl group, C3~C12 cycloalkyl group, C1~C12 straight-chain or branched alkoxy group, C3~C12 cycloalkoxy group, phenyl group, naphthyl group, biphenyl group, and terphenyl group; The intermediate is used to prepare the pyrene-containing benzanthracene compound as described in any one of claims 1 to 5; Preferably, the intermediate is selected from the following structures: 、 、 、 、 。 7. 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, wherein the organic thin film layer includes a pyrene-containing benzene-anthracene compound as described in any one of claims 1 to 5.

8. The organic electroluminescent device according to claim 7, characterized in that, The organic thin film layer includes a light-emitting layer, which includes the pyrene-containing benzanthracene compound; Preferably, the light-emitting layer comprises a host material and a dopant material, wherein the host material comprises the pyrene-containing benzanthracene compound.

9. The organic electroluminescent device according to claim 8, characterized in that, The doped material includes at least one of a compound having the structure shown in Formula II and a compound having the structure shown in Formula III: Mode ; Mode ; Mode in Ar 21 Ar 22 Each is independently selected from any one of substituted or unsubstituted C6-C20 aryl groups or substituted or unsubstituted C3-C20 heteroaryl groups; R 21 R 22 and R 23 Each is independently selected from any one of hydrogen, C1-C12 straight-chain or branched alkyl, and C6-C12 cycloalkyl; Ar 21 Ar 22 The substituents described herein are each independently selected from C1-C5 straight-chain or branched alkyl groups or C6-C12 aryl groups; Mode in Ar 31 Ar 32 Ar 33 and Ar 34 Each is independently selected from any one of substituted or unsubstituted C6-C22 aryl groups or substituted or unsubstituted C12-C40 heteroaryl groups; R 31 Selected from any one of phenyl, naphthyl, or biphenyl; a is selected from 0 or 1; Ar 31 Ar 32 Ar 33 Ar 34 The substituents described herein are each independently selected from C1-C5 straight-chain or branched alkyl groups or C6-C12 aryl groups; Preferably, formula In the middle, the Ar 21 Ar 22 Each independently selected , , , , , , , , , , , , , , , , Any one of them, the dashed line represents the connection point; Preferably, formula In, the R 21 R 22 and R 23 Each is independently selected from any one of hydrogen, methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl, or adamantyl; Preferably, formula In the middle, the Ar 31 Ar 32 Ar 33 and Ar 34 Each independently selected , , , , , , , , , Any one or at least two of the above, with dashed lines indicating connection sites; Preferably, the formula The compound is selected from any one of the following compounds: ； Preferably, the formula The compound is selected from any one of the following compounds: 。 10. The organic electroluminescent device according to claim 9, characterized in that, The light-emitting layer includes a first light-emitting layer and a second light-emitting layer. The first light-emitting layer includes a first host material and a first doped material, and the second light-emitting layer includes a second host material and a second doped material. The first host material comprises the pyrene-containing benzanthracene compound, and the second host material comprises a compound having the structure shown in Formula IV: Formula IV; In Formula IV, the Ar 11 Ar 12 Each is independently selected from any one of substituted or unsubstituted C6-C40 aryl groups or substituted or unsubstituted C12-C40 heteroaryl groups; The R 11 R 12 Each is independently selected from any one of substituted or unsubstituted C1-C6 straight-chain or branched alkyl groups, substituted or unsubstituted C6-C40 aryl groups, or substituted or unsubstituted C12-C40 heteroaryl groups; Ar 11 Ar 12 R 11 R 12 In this context, each of the substituents is independently selected from at least one of C1-C6 straight-chain or branched alkyl, C6-C20 aryl, and C6-C20 heteroaryl; The m and n are each independently selected from integers from 0 to 4; In the compound shown in Formula IV, each H atom can be independently replaced by a D atom; Preferably, the first doping material and the second doping material are the same or different, including at least one of compounds having the structure shown in Formula II and compounds having the structure shown in Formula III; Preferably, the compound represented by Formula IV is selected from any one of the following compounds: 。

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