Compound containing boron and nitrogen and organic electroluminescent device

Abstract

The invention provides a compound containing boron and nitrogen and an organic electroluminescent device. The compound containing boron and nitrogen has a structure as shown in a formula I. By designing the structure of the compound containing boron and nitrogen, the obtained compound containing boron and nitrogen has excellent performance, and the organic electroluminescent device prepared by using the compound containing boron and nitrogen as a luminescent layer material has relatively low driving voltage and relatively high current efficiency and service life.

Description

Technical Field

[0001] This invention belongs to the technical field of organic optoelectronic displays, specifically relating to a boron-nitrogen-containing compound and an organic electroluminescent device. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are display components that utilize self-emissive properties. They have a wider viewing angle and are thinner, lighter, and faster than liquid crystal displays. They can also achieve flexible displays, making them highly anticipated for use as full-color display components or lighting equipment.

[0003] Organic light emission typically refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting devices that utilize organic light emission usually have a structure that includes an anode, a cathode, and an organic layer sandwiched between the anode and the cathode.

[0004] In organic light-emitting elements (OLEDs), the organic layer is often composed of a multilayer structure made of different materials to improve efficiency and stability. For example, it may consist of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in this OLED structure, holes from the anode are injected into the organic layer, and electrons from the cathode are also injected into the organic layer. When the injected holes and electrons meet, they form excitons. When these excitons release energy and transition to the ground state, they emit photons, thus producing light. OLEDs are widely recognized for their self-emissive nature, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high-speed response.

[0005] Currently, research on organic electroluminescent materials has been widely carried out in academia and industry. Among them, blue light materials are an important component of organic electroluminescent devices, and the transmission performance and luminous efficiency of blue light materials restrict the industrialization of light-emitting devices. Therefore, designing and searching for a compound as a novel OLED material to overcome its shortcomings in practical applications is a key focus and future research trend in OLED materials research. Summary of the Invention

[0006] To address the shortcomings of existing technologies, the present invention aims to provide a boron-nitrogen-containing compound and an organic electroluminescent device. The present invention designs a boron-nitrogen-containing compound structure, resulting in a compound with excellent properties suitable for use as a light-emitting layer material in organic electroluminescent devices.

[0007] To achieve this objective, the present invention adopts the following technical solution:

[0008] In a first aspect, the present invention provides a boron-nitrogen-containing compound having the structure shown in Formula I:

[0009]

[0010] Among them, ring A, ring B, ring C, ring D, and ring E are each independently selected from any one of substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups;

[0011] And at least one hydrogen atom in ring A, ring B, ring C, ring D, or ring E is Replacement, "*" indicates a connection site;

[0012] The substituents in the C6-C30 aryl and C3-C30 heteroaryl groups are each independently selected from at least one of -D, -F, -CN, C1-C12 alkyl, C6-C30 aryl, C12-C36 diarylamine or C3-C30 heteroaryl groups;

[0013] In the boron-nitrogen-containing compound, each hydrogen atom can be independently replaced by a deuterium atom;

[0014] The boron-nitrogen-containing compounds do not include compounds BD-1 and BD-2:

[0015]

[0016] This invention designs a boron-nitrogen-containing compound structure, and the resulting boron-nitrogen-containing compound has excellent properties and is suitable for use as a light-emitting layer material in organic electroluminescent devices. The organic electroluminescent devices prepared in this way have low driving voltage, high current efficiency and long lifetime.

[0017] The following are representative structures of existing BN-based TADF materials:

[0018]

[0019] The presence of alkyl, cycloalkyl, and cycloalkyl-substituted alkyl groups in BN-based TADF materials does not contribute to luminescence itself, but it can improve the aggregation between dopants, enhance the stability of the prepared luminescent layer film, and prevent excited-state annihilation. Therefore, it is widely used to improve the performance of organic electroluminescent devices. However, the presence of these alkyl and cycloalkyl groups has a drawback; for example, for compounds... The cyclohexyl group is connected to the benzene ring via a single bond, which can rotate freely. Furthermore, the cyclohexyl group exists in both chair and boat configurations. When this material is used to fabricate organic light-emitting diodes (OLEDs), the compound in the excited state experiences energy loss due to the free rotation of the single bond. Simultaneously, at high energies, the chair and boat configurations of the cyclohexyl group interconvert, leading to energy loss in the excited state and thus reducing the luminous efficiency and lifespan of the OLED. Additionally, the carbon atom connecting the cyclohexyl group to the benzene ring contains a highly reactive hydrogen atom at the benzyl position, affecting the stability of the OLED. Moreover, the tert-butyl group contains multiple freely rotating and vibrating single bonds. Based on the above descriptions, these factors negatively impact the performance of OLEDs.

[0020] Example of compound 7 of the present invention By attaching a methyl group to the carbon atom connecting the cyclohexyl group and the benzene ring, the negative influence of the H atom at the benzene position is eliminated. At the same time, the introduction of the methyl group hinders the free rotation of the single bond connecting the benzene ring and the cyclohexyl group. In addition, the introduction of the methyl group can increase steric hindrance and reduce the interconversion between the chair and boat configurations of the cyclohexyl group. The above changes in molecular structure do not significantly reduce the film-forming properties of the material, and also improve the prevention of molecular aggregation, thus achieving good technical results.

[0021] In this invention, "D" represents a deuterium atom.

[0022] In this invention, C6-C30 can be C6, C10, C12, C15, C18, C20, C24, C26 or C30, etc.

[0023] C12-C36 can be C12, C15, C18, C20, C24, C30, or C36, etc.

[0024] C3-C30 can be C3, C4, C5, C9, C10, C14, C17, C20, C22, C23, C25, C27 or C30, etc.

[0025] In this invention, C6-C30 aryl refers to the general term for monovalent groups remaining after removing a hydrogen atom from the aromatic carbon of a C6-C30 aromatic hydrocarbon molecule; C6-C30 aryl includes C6-C30 monocyclic aryl or C6-C30 fused-ring aryl.

[0026] In this invention, C3-C30 heteroaryl refers to the general term for groups obtained by replacing one or more aromatic carbons in C3-C30 aryl groups with heteroatoms; the heteroatoms in C3-C30 heteroaryl are selected from oxygen, sulfur, nitrogen or silicon; C3-C30 heteroaryl includes C3-C30 monocyclic heteroaryl or C3-C30 fused-ring heteroaryl.

[0027] The following are preferred technical solutions of the present invention, but are not intended to limit the technical solutions provided by the present invention. The purpose and beneficial effects of the present invention can be better achieved and realized through the following preferred technical solutions.

[0028] As a preferred embodiment of the present invention, the aryl group of C6-C30 is selected from any one of phenyl, biphenyl, terphenyl, naphthyl, anthracene, indene, fluorenyl, perylene, phenanthrene, pyrene, fluoranyl, spirodifluorenyl, or benzophenanthrene, and is preferably any one of phenyl, biphenyl, naphthyl, or fluorenyl.

[0029] Preferably, the heteroatom in the C3-C30 heteroaryl group is selected from at least one of oxygen, sulfur, nitrogen, or silicon.

[0030] Preferably, the heteroaryl group of C3-C30 is selected from any one of benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazoleyl, diaryleneamine, benzofuranocarbazoleyl, benzofuranothiophenyl or triazineyl, and more preferably any one of dibenzofuranyl, dibenzothiophenyl or carbazoleyl.

[0031] Preferably, the alkyl group of C1-C12 is selected from any one of methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, p-pentyl, n-hexyl or cyclohexyl, and is more preferably any one of methyl, ethyl or tert-butyl.

[0032] Preferably, the C12-C36 diarylamine group is selected from... R 11 R 12 Each is independently selected from -H, -F, -CN, methyl, ethyl, propyl, butyl, Either phenyl or naphthyl, with "*" indicating a linking site.

[0033] As a preferred embodiment of the present invention, the A ring is selected from any one of the following substituted or unsubstituted groups: phenyl, naphthyl, 9,9-dimethylfluorenyl or carbazole;

[0034] The substituents are selected from -D, -F, -CN, methyl, ethyl, tert-butyl, ... Or any of the phenyl groups, where "*" indicates the linking site.

[0035] As a preferred embodiment of the present invention, the B ring is selected from any one of the following substituted or unsubstituted groups: phenyl, dibenzofuranyl, biphenyl or 9,9-dimethylfluorenyl;

[0036] The substituents are selected from -D, -F, -CN, methyl, ethyl, tert-butyl, ... Any of the above, where "*" indicates a connection site.

[0037] As a preferred embodiment of the present invention, the C ring is selected from the following groups, whether substituted or unsubstituted: phenyl or biphenyl;

[0038] The substituents are selected from -D, -F, -CN, methyl, ethyl, tert-butyl, ... Any one of them;

[0039] R 11 R 12 Each is independently selected from -H, tert-butyl, Any of the above, where "*" indicates a connection site.

[0040] As a preferred embodiment of the present invention, the D ring is selected from any one of the following substituted or unsubstituted groups: phenyl, dibenzofuranyl, biphenyl or 9,9-dimethylfluorenyl;

[0041] The substituents are selected from -D, -F, -CN, methyl, ethyl, tert-butyl, ... Any of the above, where "*" indicates a connection site.

[0042] As a preferred embodiment of the present invention, the E ring is selected from any one of the following substituted or unsubstituted groups: phenyl, naphthyl, 9,9-dimethylfluorenyl or carbazole;

[0043] The substituents are selected from -D, -F, -CN, methyl, ethyl, tert-butyl, phenyl, etc. Any one of them, where "*" indicates a connection site;

[0044] R 11 R 12 Each is independently selected from -H, tert-butyl, Any one of them.

[0045] As a preferred embodiment of the present invention, the boron-nitrogen-containing compound has the structure shown in Formula I-1, Formula I-2 or Formula I-3 as follows:

[0046]

[0047] Among them, R1, R2, and R4 are selected from -H, -D, -F, -CN, methyl, ethyl, tert-butyl, ... Or any one of the phenyl groups;

[0048] R3 is selected from -H, -D, -F, -CN, methyl, ethyl, tert-butyl, Any one of them;

[0049] R5 is selected from -H, -D, -F, -CN, methyl, ethyl, tert-butyl, Any one of them;

[0050] R 11 R 12 Each is independently selected from -H, tert-butyl, Any one of them;

[0051] m and n each independently represent 0, 1, 2 or 3;

[0052] Ar1 and Ar2 are each independently selected from any one of dibenzofuranyl, biphenyl, or 9,9-dimethylfluorenyl;

[0053] The boron-nitrogen-containing compound includes at least one

[0054] "*" indicates a connection point;

[0055] In the boron-nitrogen-containing compound, each hydrogen atom can be independently replaced by a deuterium atom.

[0056] It should be noted that in the compound of formula I-1, if m represents 2 or 3, the corresponding 2 or 3 R2s can be the same or different; similarly, if n represents 2 or 3, the corresponding 2 or 3 R4s can be the same or different.

[0057] As a preferred embodiment of the present invention, the boron-nitrogen-containing compound is selected from any one of compounds 1 to 68:

[0058]

[0059]

[0060]

[0061] Preferably, the boron-nitrogen-containing compound is selected from the following compounds:

[0062]

[0063]

[0064] This invention lists some specific structural forms of the boron-nitrogen-containing compounds, but the boron-nitrogen-containing compounds of this invention are not limited to these listed chemical structures. Any structure based on the structure shown in Formula I, in which rings A, B, C, D, and E satisfy the above-mentioned limiting conditions, should be included.

[0065] It should also be noted that the present invention does not impose any special restrictions on the preparation method of the compound of formula I, and all commonly used preparation methods in the art are applicable.

[0066] In a second aspect, the present invention provides an organic electroluminescent device, the organic electroluminescent device comprising the boron-nitrogen-containing compound as described in the first aspect.

[0067] Preferably, the organic electroluminescent device includes a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, the organic layer including a light-emitting layer, the material of the light-emitting layer including boron-nitrogen compounds as described in the first aspect.

[0068] Preferably, the doping material of the light-emitting layer comprises a boron-nitrogen-containing compound as described in the first aspect.

[0069] Preferably, the light-emitting layer is prepared using a solution method.

[0070] Thirdly, the present invention provides a display device comprising the organic electroluminescent device as described in the second aspect.

[0071] Compared with the prior art, the present invention has the following beneficial effects:

[0072] This invention designs the structure of boron-nitrogen-containing compounds to obtain compounds with good luminescent properties, which can be used to prepare organic electroluminescent devices. In particular, as a light-emitting layer material in organic electroluminescent devices, it can effectively reduce the driving voltage of organic electroluminescent devices and improve the current efficiency and lifespan of organic electroluminescent devices. Detailed Implementation

[0073] To facilitate understanding of the present invention, the following embodiments are provided. Those skilled in the art should understand that the preparation examples and embodiments are merely illustrative and should not be considered as specific limitations of the invention.

[0074] Synthesis Example 1

[0075] This synthetic example provides compound 1 and its synthetic method, which is as follows:

[0076]

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

[0078] Under nitrogen protection, 200 mL of dry toluene, 0.1 mol of 3,5-dibromochlorobenzene, 0.2 mol of diphenylamine, 0.001 mol of Pd(dba)2 (bis(dibenzylacetone)palladium), 4 g of 10% (w / w) tritert-tert-butylphosphine toluene solution (0.002 mol of tritert-tert-butylphosphine) and 0.3 mol of sodium tert-butoxide were added to a 100 mL three-necked flask. The mixture was heated to reflux for 12 h, then cooled to room temperature, water was added to dissolve the mixture, and the organic layer was washed with water until neutral. The mixture was dried with magnesium sulfate, filtered to remove magnesium sulfate, concentrated to dryness, and crystallized with ethanol to obtain intermediate 1-1.

[0079] Mass spectrometry analysis of intermediate 1-1 showed a mass-to-charge ratio (m / z) of 446.2.

[0080] (2) Synthesis of intermediates 1-2

[0081] Under nitrogen protection, 300 mL of dry toluene, 30 mL of water, 0.1 mol of intermediate 1-1, 0.3 mol of 1-methylcyclohexylboronic acid, 0.001 mol of Pd(dba)2 (bis(dibenzylacetone)palladium), 0.01 mol of xphos (2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl), and 0.3 mol of potassium phosphate were added to a 100 mL three-necked flask. The mixture was heated to 110 °C and reacted for 10 h. After cooling to room temperature, water was added to liquefy the mixture. The organic layer was then washed with water until neutral, dried with magnesium sulfate, filtered to remove magnesium sulfate, concentrated to dryness, and crystallized with ethanol to obtain intermediate 1-2.

[0082] Mass spectrometry analysis of intermediates 1-2 revealed a mass-to-charge ratio (m / z) of 508.3.

[0083] (3) Synthesis of Compound 1

[0084] Under nitrogen protection and oil bath heating, 200 mL of dry o-dichlorobenzene, 0.01 mol of intermediate 1-2, and 0.00 6 mol of anhydrous nickel chloride were added to a 500 mL three-necked flask. The mixture was stirred until homogeneous, and the temperature was maintained at 20℃-25℃. 20 mL of a 1.0 M solution of BBr3 in dichloromethane (containing 0.02 mol of BBr3) was slowly added dropwise. After the addition was complete, the temperature was slowly increased to the oil bath temperature of 40℃ and reacted for 2 hours. Then, the temperature was slowly increased to the oil bath temperature of 100℃, during which the dichloromethane in the reaction system was distilled off. The reaction was then maintained at 100℃ for 4 hours, followed by increasing the temperature to the oil bath temperature of 140℃ and reacting for 12 hours. The mixture was then cooled to room temperature, and 0.05 mol of... The reaction was terminated with N-ethyldiisopropylamine; water was added to the liquid, the organic layer was washed with water until neutral, dried with magnesium sulfate, filtered to remove magnesium sulfate, concentrated to dryness, separated by silica gel column chromatography, eluted with petroleum ether:ethyl acetate = 20:0.5 (v / v), to give compound 1.

[0085] The obtained compound 1 was analyzed by mass spectrometry: the mass-to-charge ratio (m / z) was found to be 516.3.

[0086] Synthesis Example 2

[0087] This synthetic example provides compound 2 and its synthetic method, which is as follows:

[0088]

[0089] Following the synthesis method of compound 1 provided in Synthesis Example 1, diphenylamine was replaced with an equal amount of di(tert-butylphenyl)amine, while other conditions remained unchanged, to obtain compound 2.

[0090] The obtained compound 2 was analyzed by mass spectrometry: the mass-to-charge ratio (m / z) was measured to be 740.5.

[0091] Synthesis Example 3

[0092] This synthetic example provides compound 7 and its synthetic method, which is as follows:

[0093]

[0094] (1) Synthesis of intermediate 7-0

[0095] Under nitrogen protection, 200 mL of dry toluene, 0.1 mol of 4-(1-methylcyclohexyl)bromobenzene, 0.1 mol of 4-(1-methylcyclohexyl)aniline, 0.001 mol of Pd(dba)2 (bis(dibenzylacetone)palladium), 4 g of a 10% (w / w) tri-tert-butylphosphine toluene solution (0.002 mol of tri-tert-butylphosphine) and 0.3 mol of sodium tert-butoxide were added to a 100 mL three-necked flask. The mixture was heated to reflux for 12 h, then cooled to room temperature, water was added to dissolve the mixture, and the organic layer was washed with water until neutral. The mixture was dried with magnesium sulfate, filtered to remove magnesium sulfate, concentrated to dryness, and crystallized with ethanol to obtain intermediate 7-0.

[0096] Mass spectrometry analysis of intermediate 7-0 revealed a mass-to-charge ratio (m / z) of 361.3.

[0097] (2) Synthesis of intermediate 7-1

[0098] Following the synthesis method of intermediate 1-1 in Synthesis Example 1, by replacing diphenylamine with an equal amount of intermediate 7-0, while keeping other conditions unchanged, intermediate 7-1 can be obtained.

[0099] Mass spectrometry analysis of intermediate 7-1 revealed a mass-to-charge ratio (m / z) of 796.6.

[0100] (3) Synthesis of compound 7

[0101] Following the synthesis method of Example 1, intermediate 1-2 was replaced with intermediate 7-1, while other conditions remained unchanged, to obtain compound 7.

[0102] Mass spectrometry analysis of compound 7 showed a mass-to-charge ratio (m / z) of 804.6.

[0103] Synthesis Example 4

[0104] This synthetic example provides compound 25 and its synthetic method, which is as follows:

[0105]

[0106] Following the synthetic method of compound 1 in Synthesis Example 1, methylcyclohexylboronic acid was replaced with an equal amount of methylcyclopentylboronic acid to obtain compound 25.

[0107] Mass spectrometry analysis of compound 25 showed a mass-to-charge ratio (m / z) of 502.3.

[0108] Synthesis Example 5

[0109] This synthetic example provides compound 26 and its synthetic method, which is as follows:

[0110]

[0111] Following the synthesis method of compound 2 in Synthesis Example 2, methylcyclohexylboronic acid was replaced with an equal amount of methylcyclopentylboronic acid, while other conditions remained unchanged, to obtain compound 26.

[0112] Mass spectrometry analysis of compound 26 revealed a mass-to-charge ratio (m / z) of 726.5.

[0113] Synthesis Example 6

[0114] This synthetic example provides compound 52 and its synthetic method, which is as follows:

[0115]

[0116] 0.01 mol of compound 2 was added to a reaction flask, along with 160 ml of deuterium benzene and 0.05 mol of trifluoromethanesulfonic anhydride. The mixture was heated to 80 °C under nitrogen protection and kept at that temperature for 24 h. After cooling to room temperature, the reaction was quenched with a saturated sodium bicarbonate aqueous solution and washed with water until neutral. The mixture was dried with anhydrous magnesium sulfate and passed through a silica gel column. The crude product was recrystallized from toluene and ethanol to obtain compound 52.

[0117] The obtained compound 52 was analyzed by mass spectrometry: the mass-to-charge ratio (m / z) was measured to be 756.6.

[0118] Other compounds for which specific synthetic steps are not listed can be prepared using common knowledge in the art, combined with conventional methods in the art and the above synthetic examples.

[0119] The specific structures of the compounds used in the following device embodiments and device comparative examples are shown below:

[0120]

[0121] In the following device embodiments, the compounds provided by the present invention are selected as doping materials for the light-emitting layer in organic electroluminescent devices, and the device comparative examples use the above-mentioned BD-1, BD-2, and BD-3 as doping materials for the light-emitting layer in organic electroluminescent devices.

[0122] Device Example 1

[0123] This embodiment of the device provides an organic electroluminescent device, using compound 1 provided in the synthesis embodiment 1 of the present invention as the doping material for the light-emitting layer; and in this embodiment, the light-emitting layer is prepared by solution method.

[0124] The organic electroluminescent device has the following structure:

[0125] ITO / HT (40nm) / BH: Compound 1 3% / TPBI (30nm) / LiF (0.5nm) / Al (150nm).

[0126] The fabrication method of the above-mentioned organic electroluminescent device is as follows:

[0127] The glass substrate coated with an ITO transparent conductive layer (as the anode) was ultrasonically treated in a cleaning agent, then rinsed in deionized water, then ultrasonically degreased in a mixed solvent of acetone and ethanol, then baked in a clean environment until completely dehydrated, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam to improve the surface properties and enhance the bonding ability with the hole injection layer.

[0128] The glass substrate was placed in a vacuum chamber and evacuated to a vacuum level of 1×10⁻⁶. -5 ~9×10 -3 Pa, HT is vacuum-deposited on the anode as a hole transport layer at a deposition rate of 0.1 nm / s and a film thickness of 40 nm;

[0129] The glass substrate with the hole transport layer already deposited was transferred to a nitrogen-filled glove box. A light-emitting layer solution was then spin-coated onto the hole transport layer. The light-emitting layer solution consisted of a solute and a solvent. The solute included BH and 5% (by mass) of Compound 1. The solvent was 4-cyclohexylbenzene and chlorobenzene, with a 4-cyclohexylbenzene:chlorobenzene ratio of 3:1 (volume ratio). The spin-coating speed was 1000 rpm for 60 seconds. The glass substrate was then heated at 80°C for 2 hours, and the solvent was removed under vacuum. By adjusting the concentrations of BH and Compound 1 in the solvent, the thickness of the resulting light-emitting layer was adjusted to approximately 30–40 nm, as shown in Table 1 (the unit for light-emitting layer thickness is nm).

[0130] The glass substrate with the light-emitting layer already spin-coated in the previous step is transferred to the vacuum chamber, and TPBI is vacuum-deposited on the light-emitting layer as the electron transport layer of the device. The deposition rate is 0.1 nm / s and the total film thickness is 30 nm.

[0131] 0.5 nm LiF and 150 nm Al were vacuum-deposited on the electron transport layer as the electron injection layer and cathode, respectively.

[0132] The brightness, driving voltage, and current efficiency of the prepared organic electroluminescent device were measured.

[0133] Device Examples 2-10

[0134] Device Examples 2-10 each provide an organic electroluminescent device, which differs from Device Example 1 only in that the doping material of the light-emitting layer is different (see Table 1 for details), while other conditions are the same as those in Device Example 1.

[0135] Device Comparison Examples 1-3

[0136] Comparative Examples 1-3 each provide an organic electroluminescent device, which differs from Device Example 1 only in that the doping material of the light-emitting layer is different (see Table 1 for details), while other conditions are the same as those in Device Example 1.

[0137] Performance testing

[0138] The driving voltage, current efficiency, and lifetime (LT90) of the OLED devices provided above were tested. LT90 refers to the time required for the brightness to decrease to 90% of its original brightness while maintaining an initial brightness of 1000 nits at a constant current density. Test items included the brightness, driving voltage, and current efficiency of the organic electroluminescent device. The driving voltage, current efficiency, and LT90 data were all based on a brightness of 1000 cd / m². 2 The relative values ​​at different times (with BD-3 as the benchmark). The performance test results of organic electroluminescent devices are shown in Table 1 below.

[0139] Table 1

[0140]

[0141] As can be seen from the above, the present invention designs the structure of boron-nitrogen compounds to obtain boron-nitrogen compounds with good luminescent properties, which can be used to prepare organic electroluminescent devices. In particular, as a light-emitting layer material in organic electroluminescent devices, it can effectively reduce the driving voltage of organic electroluminescent devices and improve the current efficiency and lifespan of organic electroluminescent devices.

[0142] 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 boron-nitrogen-containing compound, characterized in that, The boron-nitrogen-containing compound has the structure shown in Formula I: Among them, ring A, ring B, ring C, ring D, and ring E are each independently selected from any one of substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups; And at least one hydrogen atom in ring A, ring B, ring C, ring D, or ring E is Replacement, "*" indicates a connection site; The substituents in the C6-C30 aryl and C3-C30 heteroaryl groups are each independently selected from at least one of -D, -F, -CN, C1-C12 alkyl, C6-C30 aryl, C12-C36 diarylamine or C3-C30 heteroaryl groups; In the boron-nitrogen-containing compound, each hydrogen atom can be independently replaced by a deuterium atom; The boron-nitrogen-containing compounds do not include compounds BD-1 and BD-2:

2. The boron-nitrogen-containing compound according to claim 1, characterized in that, The aryl group of C6-C30 is selected from any one of phenyl, biphenyl, terphenyl, naphthyl, anthracene, indene, fluorenyl, perylene, phenanthrene, pyrene, fluoranyl, spirodifluorenyl, or benzophenanthrene, preferably any one of phenyl, biphenyl, naphthyl, or fluorenyl. Preferably, the heteroatom in the C3-C30 heteroaryl group is selected from at least one of oxygen, sulfur, nitrogen, or silicon; Preferably, the heteroaryl group of C3-C30 is selected from any one of benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazoleyl, diaryleneamine, benzofuranocarbazoleyl, benzofuranothiophenyl or triazineyl, and is more preferably any one of dibenzofuranyl, dibenzothiophenyl or carbazoleyl; Preferably, the alkyl group of C1-C12 is selected from any one of methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, p-pentyl, n-hexyl or cyclohexyl, and is more preferably any one of methyl, ethyl or tert-butyl; Preferably, the C12-C36 diarylamine group is selected from... R 11 R 12 Each is independently selected from -H, -F, -CN, methyl, ethyl, propyl, butyl, Either phenyl or naphthyl, with "*" indicating the linking site.

3. The boron-nitrogen-containing compound according to claim 1 or 2, characterized in that, The A ring is selected from any one of the following groups, whether substituted or unsubstituted: phenyl, naphthyl, 9,9-dimethylfluorenyl or carbazole; The substituents are selected from -D, -F, -CN, methyl, ethyl, tert-butyl, ... Or any of the phenyl groups, "*" indicates the linking site.

4. The boron-nitrogen-containing compound according to any one of claims 1-3, characterized in that, The B ring is selected from any one of the following groups, substituted or unsubstituted: phenyl, dibenzofuranyl, biphenyl or 9,9-dimethylfluorenyl; The substituents are selected from -D, -F, -CN, methyl, ethyl, tert-butyl, ... Any of the above, where "*" represents a connection site.

5. The boron-nitrogen-containing compound according to any one of claims 1-4, characterized in that, The C ring is selected from substituted or unsubstituted groups such as phenyl or biphenyl; The substituents are selected from -D, -F, -CN, methyl, ethyl, tert-butyl, ... Any one of them; R 11 R 12 Each is independently selected from -H, tert-butyl, Any of the above, where "*" represents a connection site.

6. The boron-nitrogen-containing compound according to any one of claims 1-5, characterized in that, The D ring is selected from any one of the following groups, substituted or unsubstituted: phenyl, dibenzofuranyl, biphenyl or 9,9-dimethylfluorenyl; The substituents are selected from -D, -F, -CN, methyl, ethyl, tert-butyl, ... Any of the above, where "*" represents a connection site.

7. The boron-nitrogen-containing compound according to claim 1, characterized in that, The E ring is selected from any one of the following groups, whether substituted or unsubstituted: phenyl, naphthyl, 9,9-dimethylfluorenyl or carbazole; The substituents are selected from -D, -F, -CN, methyl, ethyl, tert-butyl, phenyl, etc. Any of the above, "*" indicates a connection site; R 11 R 12 Each is independently selected from -H, tert-butyl, Any one of them.

8. The boron-nitrogen-containing compound according to any one of claims 1-7, characterized in that, The boron-nitrogen-containing compound has the structure shown in Formula I-1, Formula I-2, or Formula I-3 as follows: Among them, R1, R2, and R4 are selected from -H, -D, -F, -CN, methyl, ethyl, tert-butyl, ... Or any one of the phenyl groups; R3 is selected from -H, -D, -F, -CN, methyl, ethyl, tert-butyl, Any one of them; R5 is selected from -H, -D, -F, -CN, methyl, ethyl, tert-butyl, Any one of them; R 11 R 12 Each is independently selected from -H, tert-butyl, Any one of them; m and n can each independently represent 0, 1, 2 or 3; Ar1 and Ar2 are each independently selected from any one of dibenzofuranyl, biphenyl, or 9,9-dimethylfluorenyl; The boron-nitrogen-containing compound includes at least one "*" indicates a connection site; In the boron-nitrogen-containing compound, each hydrogen atom can be independently replaced by a deuterium atom.

9. The boron-nitrogen-containing compound according to any one of claims 1-8, characterized in that, The boron-nitrogen-containing compound is selected from any one of compounds 1 to 68:

10. An organic electroluminescent device, characterized in that, The organic electroluminescent device comprises the boron-nitrogen-containing compound according to any one of claims 1-9; Preferably, the organic electroluminescent device includes a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, the organic layer including a light-emitting layer, the material of the light-emitting layer including a boron-nitrogen-containing compound as described in any one of claims 1-9; Preferably, the doping material of the light-emitting layer includes a boron-nitrogen-containing compound as described in any one of claims 1-9.

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