Boron-nitrogen compound containing pyridine and carbazolyl and application thereof

Abstract

The invention provides a boron-nitrogen compound containing pyridine and carbazolyl and application thereof, the boron-nitrogen compound containing pyridine and carbazolyl has a structure as shown in a formula I. The boron-nitrogen compound containing pyridine and carbazolyl has excellent performance by designing the structure of the boron-nitrogen compound, and the boron-nitrogen compound containing pyridine and carbazolyl can be applied to the field of chemical industry. The material is suitable for luminescent layer materials in organic electroluminescent devices.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic photoelectric display, and in particular relates to a boron nitrogen compound containing pyridine and carbazole groups and application thereof. Background Art

[0002] Organic light emitting diodes (OLEDs) are display components that utilize self-luminescence. They have a wide viewing angle and are thinner and lighter than liquid crystal displays (LCDs), have a faster response speed, and can achieve flexible displays. Therefore, their application as full-color display components or lighting devices is highly anticipated.

[0003] Generally, organic light emitting diodes (OLEDs) utilize organic light emitting diodes (ELDs) that convert electrical energy into light energy using organic materials. OLEDs typically have a structure including an anode, a cathode, and an organic material layer interposed between the anode and cathode.

[0004] To improve the efficiency and stability of organic light-emitting devices, the organic layer is often composed of a multilayer structure composed of different materials. For example, it can be composed 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 organic light-emitting device 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, excitons are formed. When the excitons release energy and transition to the ground state, they emit photons, generating light. Such organic light-emitting devices are widely recognized to have characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high-speed responsiveness.

[0005] Currently, research on organic electroluminescent materials is widespread in academia and industry. Blue-light-emitting materials are a crucial component of organic electroluminescent devices, and their transmission performance and luminous efficiency constrain the industrialization of these devices. Therefore, designing and finding compounds as novel OLED materials to overcome their shortcomings in practical applications is a key focus and future development trend in OLED material research. Summary of the Invention

[0006] In view of the shortcomings of the prior art, the purpose of the present invention is to provide a boron nitrogen compound containing pyridine and carbazole groups and its application. By designing the structure of the boron nitrogen compound, the present invention obtains a boron nitrogen compound containing pyridine and carbazole groups with excellent performance and is suitable for use as a light-emitting layer material in organic electroluminescent devices.

[0007] To achieve this object, the present invention adopts the following technical solutions:

[0008] In one aspect, the present invention provides a boron-nitrogen compound containing pyridine and carbazole groups, wherein the boron-nitrogen compound containing pyridine and carbazole groups has a structure as shown in Formula I:

[0009]

[0010] X is selected from oxygen, sulfur or Where * represents the attachment site of the group;

[0011] In Formula I, R1, R2, R3, R4, R5, R6, and R7 are the same or different from each other and are independently selected from hydrogen, deuterium, substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted C3~C 30 heteroaryl;

[0012] Ar1, Ar2 and Ar3 are each independently selected from substituted or unsubstituted C6 to C 30 aryl, substituted or unsubstituted C3~C 30 heteroaryl;

[0013] When the substituted or unsubstituted group contains a substituent, the substituent is selected from deuterium, F, CN, C1-C 12 Alkyl, C6~C 30 Aryl or C3~C 30 heteroaryl;

[0014] All hydrogen atoms in formula I can be independently replaced by deuterium, F, CN, C1-C 12 Alkyl, C6~C 30 Aryl or C3~C 30 is substituted with a heteroaryl group.

[0015] Preferably, the C1 to C 12 The alkyl group is selected from methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, tert-pentyl, n-hexyl or cyclohexyl.

[0016] More preferably, the C1 to C 12 The alkyl group is selected from methyl, ethyl, isopropyl or tert-butyl.

[0017] The C6~C 30 The aryl group is the general term for the monovalent group left after removing a hydrogen atom from the aromatic carbon of the aromatic hydrocarbon molecule; 30 The aryl group includes a monocyclic aryl group or a condensed ring aryl group.

[0018] Preferably, the C6~C 30The aryl group of is selected from phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, indenyl, fluorenyl, perylenyl, phenanthrenyl, pyrenyl, fluoranthenyl, fluorenyl, spirobifluorenyl or triphenylenyl.

[0019] More preferably, the C6~C 30 The aryl group is selected from phenyl, biphenyl and naphthyl.

[0020] The C3~C 30 The heteroaryl group is a general term for groups in which one or more aromatic carbon atoms in an aromatic group are replaced by heteroatoms; 30 The heteroatoms of the heteroaryl group are selected from oxygen, sulfur, nitrogen or silicon; the C3 to C 30 The heteroaryl group includes a monocyclic heteroaryl group or a condensed-ring heteroaryl group.

[0021] Preferably, the C3~C 30 The heteroaryl group is selected from pyridyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, diarylideneamine, benzofuranocarbazolyl, benzofuranothiophenyl or triazine.

[0022] More preferably, the C3 to C 30 The heteroaryl group is selected from pyridyl, dibenzofuranyl, dibenzothienyl or carbazolyl.

[0023] Preferably, R1, R2, R3, R4, R5, R6, R7 are the same as or different from each other and are each independently selected from hydrogen, deuterium, methyl, tert-butyl, phenyl, The wavy line represents the attachment site of the group.

[0024] Preferably, Ar1, Ar2 and Ar3 are each independently selected from phenyl, biphenyl,

[0025] Preferably, the boron-nitrogen compound is selected from any one of compounds 1 to 72:

[0026]

[0027]

[0028]

[0029]

[0030]

[0031] The present invention lists some specific structural forms of the boron nitrogen compounds, but the boron nitrogen compounds of the present invention are not limited to these listed chemical structures. Any structure based on the structure shown in Formula I in which X, R1, R2, R3, R4, R5, R6, R7, Ar1, Ar2 and Ar3 meet the above-mentioned limiting conditions should be included.

[0032] In a second aspect, the present invention provides an organic electroluminescent device, comprising the boron nitrogen compound containing pyridine and carbazole groups as described in the first aspect.

[0033] Preferably, the organic electroluminescent device comprises a first electrode, a second electrode and an organic layer disposed between the first electrode and the second electrode, and the material of the organic layer comprises the boron nitrogen compound containing pyridine and carbazole groups as described in the first aspect.

[0034] Preferably, the organic layer includes a light-emitting layer, and the material of the light-emitting layer includes the boron nitrogen compound containing pyridine and carbazole groups as described in the first aspect.

[0035] Furthermore, the light-emitting layer is prepared by an evaporation method.

[0036] In a third aspect, the present invention provides a display device, comprising the organic electroluminescent device according to the second aspect.

[0037] Compared with the prior art, the present invention has the following beneficial effects:

[0038] The present invention designs the structure of the boron-nitrogen compound to obtain a boron-nitrogen compound containing pyridine and carbazole groups with good luminescence properties. The boron-nitrogen compound can be used to prepare organic electroluminescent devices, especially as a light-emitting layer material in organic electroluminescent devices, and can effectively reduce the driving voltage of the organic electroluminescent device and improve the current efficiency of the organic electroluminescent device. DETAILED DESCRIPTION

[0039] The technical solution of the present invention is further described below by way of specific embodiments. It should be understood by those skilled in the art that the embodiments are merely to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0040] Preparation Example 1

[0041] This preparation example provides a method for synthesizing intermediate 1, which is as follows:

[0042]

[0043] (1) Synthesis of intermediate 1-1

[0044] Under nitrogen protection, to a 500 mL three-necked flask, were added 200 mL of dry toluene, 0.1 mol of 4-tert-butyl-2,6-dibromopyridine, 0.1 mol of carbazole, 0.001 mol of Pd(dba)2 (bis(dibenzylideneacetonepalladium), 4 g of a 10% by weight tri-tert-butylphosphine toluene solution (the amount of tri-tert-butylphosphine was 0.002 mol), and 0.3 mol of sodium tert-butoxide. The mixture was heated to reflux for 12 h, 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 recrystallized from ethanol to obtain intermediate 1-1.

[0045] The intermediate 1-1 was subjected to mass spectrometry detection, and the mass-to-charge ratio (m / z) was measured to be 378.1.

[0046] (2) Synthesis of Intermediate 1

[0047] Under full nitrogen protection, 400 mL of toluene, 200 mL of ethanol, 200 mL of water, 0.1 mol of intermediate 1-1, 0.15 mol of 4-chlorophenylboronic acid, 0.2 mol of potassium carbonate and 0.05 mol of tetrakis(triphenylphosphine)palladium were added to the reaction flask, the temperature was raised to 78 ° C and stirred for reaction for 6 h, then cooled to room temperature for separation, the obtained organic phase was dried over magnesium sulfate and then subjected to column chromatography, the chromatographic solution was concentrated and recrystallized from ethanol to obtain intermediate 1.

[0048] The mass spectrometry of intermediate 1 showed a mass-to-charge ratio (m / z) of 410.2.

[0049] Preparation Example 2

[0050] This preparation example provides a method for synthesizing intermediate 2, which is as follows:

[0051]

[0052] (1) Synthesis of intermediate 2-2

[0053] Under nitrogen protection, to a 500 mL three-necked flask, were added 200 mL of dry toluene, 0.1 mol of intermediate 2-1, 0.1 mol of carbazole, 0.001 mol of Pd(dba)2 (bis(dibenzylideneacetonepalladium), 4 g of a 10% by weight tri-tert-butylphosphine toluene solution (the amount of tri-tert-butylphosphine was 0.002 mol), and 0.3 mol of sodium tert-butoxide. The mixture was heated to reflux for 12 h, 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 recrystallized from ethanol to obtain intermediate 2-2.

[0054] The intermediate 2-2 was subjected to mass spectrometry detection: the measured mass spectrum (m / z) was 354.1.

[0055] (2) Synthesis of intermediate 2-3

[0056] 0.1 mol of intermediate 2-2, 0.15 mol of pinacol diboronate, 0.3 mol of potassium acetate, 0.005 mol of Pd2(dba)3 (trisdibenzylideneacetone dipalladium), 0.01 mol of xphos (2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl) and 400 mL of toluene were added to the reaction flask, refluxed under nitrogen for 8 h, then cooled to room temperature, the catalyst and salt were filtered off, and the filtrate was directly subjected to silica gel column chromatography. The obtained chromatographic solution was concentrated to dryness and recrystallized with ethanol to obtain intermediate 2-3.

[0057] The intermediate 2-3 was subjected to mass spectrometry detection: the measured mass spectrum (m / z) was 446.2.

[0058] (4) Synthesis of Intermediate 2

[0059] Under full nitrogen protection, 400 mL of toluene, 200 mL of ethanol, 200 mL of water, 0.1 mol of intermediate 2-3, 0.12 mol of p-bromoiodobenzene, 0.2 mol of potassium carbonate and 0.05 mol of tetrakis(triphenylphosphine)palladium were added to the reaction flask, the temperature was raised to 78 ° C and stirred for 6 h, the liquid was separated, the organic phase was dried and then subjected to column chromatography, the filtrate was concentrated, and the obtained solid was recrystallized from ethanol to obtain intermediate 2.

[0060] The mass spectrometry of intermediate 2 showed a mass-to-charge ratio (m / z) of 474.1.

[0061] Preparation Example 3

[0062] This preparation example provides a method for synthesizing intermediate 3, which is as follows:

[0063]

[0064] Referring to the synthesis method of Preparation Example 2, Intermediate 3 can be obtained by replacing Intermediate 2-1 in Preparation Example 2 with an equal molar amount of Intermediate 3-1 and replacing carbazole in Preparation Example 2 with an equal molar amount of 3,6-di-tert-butylcarbazole, while keeping other conditions unchanged.

[0065] The intermediate 3 was subjected to mass spectrometry detection: the measured charge-to-mass ratio (m / z) was 642.3.

[0066] Preparation Example 4

[0067] This preparation example provides a method for synthesizing intermediate 4, which is as follows:

[0068]

[0069] Referring to the synthesis method of Synthesis Example 3, Intermediate 4 can be obtained by replacing Intermediate 3-1 in Preparation Example 3 with Intermediate 4-1 in an equal molar amount while keeping other conditions unchanged.

[0070] The mass spectrometry of intermediate 4 was performed, and the charge-to-mass ratio (m / z) was measured to be 675.2.

[0071] Synthesis Example 1

[0072] This embodiment provides a method for synthesizing compound 5, which is as follows:

[0073]

[0074] (1) Synthesis of Intermediate 5-1

[0075] Under nitrogen protection, to a 500 mL three-necked flask, were added 200 mL of dry toluene, 0.1 mol of intermediate 1, 0.1 mol of diamine-1, 0.001 mol of Pd(dba)2 (bis(dibenzylideneacetonepalladium), 4 g of a 10% by weight tri-tert-butylphosphine toluene solution (the amount of tri-tert-butylphosphine was 0.002 mol), and 0.3 mol of sodium tert-butoxide. The mixture was heated to reflux for 12 h, 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 recrystallized from toluene and ethanol to obtain intermediate 5-1.

[0076] The intermediate 5-1 was subjected to mass spectrometry detection, and the mass-to-charge ratio (m / z) was measured to be 634.3.

[0077] (2) Synthesis of Intermediate 5-2

[0078] Referring to the synthesis method of intermediate 5-1, an equal molar amount of intermediate 5-1 is used to replace diamine-1 in the synthesis step of intermediate 5-1, and an equal molar amount of 3-bromobenzofuran is used to replace intermediate 1 in the synthesis step of intermediate 5-1. Other conditions remain unchanged to obtain intermediate 5-2;

[0079] The intermediate 5-2 was subjected to mass spectrometry detection, and the mass-to-charge ratio (m / z) was measured to be 750.3.

[0080] (3) Synthesis of compound 5

[0081] 0.01 mol of intermediate 5-2 was dissolved in 100 mL of o-dichlorobenzene. After nitrogen was fully evacuated and replaced, 0.03 mol of boron tribromide was added dropwise at 25°C. After the addition was complete, the temperature was raised to 160°C and refluxed for 24 hours. After the reaction was completed, the temperature was lowered to 0°C, and 0.15 mol of N,N-diisopropylethylamine (DIPEA) was added dropwise. After the addition was complete, the temperature was maintained at -5°C to 0°C for 2 hours. Then, o-dichlorobenzene was removed by distillation under reduced pressure. The crude product was dissolved in toluene and passed through a silica gel column. The resulting chromatographic solution was concentrated and recrystallized with toluene and ethanol to obtain compound 5.

[0082] Compound 5 was detected by mass spectrometry, and the mass-to-charge ratio (m / z) was measured to be 758.3.

[0083] Synthesis Example 2

[0084] This example provides a method for synthesizing compound 12, which is as follows:

[0085]

[0086] Referring to the synthesis method of Synthesis Example 1, intermediate 1 in Synthesis Example 1 was replaced by an equal molar amount of intermediate 3, and 3-bromobenzofuran in Synthesis Example 1 was replaced by an equal molar amount of 3-bromobenzothiophene. Compound 12 can be obtained while keeping other conditions unchanged.

[0087] Compound 12 was detected by mass spectrometry, and the charge-to-mass ratio (m / z) was measured to be 962.5.

[0088] Synthesis Example 3

[0089] This example provides a method for synthesizing compound 16, which is as follows:

[0090]

[0091] Referring to the synthesis method of Synthesis Example 2, an equal molar amount of diamine-2 was used to replace the intermediate diamine-1 in Synthesis Example 2, and an equal molar amount of 3-bromo-5-tert-butylbenzothiophene was used to replace the 3-bromobenzothiophene in Synthesis Example 2. Compound 16 can be obtained while keeping other conditions unchanged.

[0092] Compound 16 was detected by mass spectrometry, and the charge-to-mass ratio (m / z) was measured to be 1186.7.

[0093] Synthesis Example 4

[0094] This example provides a method for synthesizing compound 18, which is as follows:

[0095]

[0096] (1) Synthesis of intermediate 18-0

[0097] Under nitrogen protection, 200 mL of dry toluene, 0.1 mol of 3,5-diiodochlorobenzene, 0.22 mol of 4-tert-butylaniline, 0.001 mol of Pd(dba)2 (bis(dibenzylideneacetonepalladium), 4 g of a 10% by weight tri-tert-butylphosphine toluene solution (the amount of tri-tert-butylphosphine is 0.002 mol), and 0.3 mol of sodium tert-butoxide were added to a 500 mL three-necked flask. The mixture was heated to reflux for 12 h, 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 recrystallized from ethanol to obtain intermediate 18-0-1.

[0098] The intermediate 18-0-1 was subjected to mass spectrometry detection, and the mass-to-charge ratio (m / z) was measured to be 406.2.

[0099] Under nitrogen protection, to a 100 mL three-necked flask were added 40 mL of dry toluene, 0.01 mol of intermediate 18-0-1, 0.012 mol of carbazole, 0.0001 mol of Pd(dba)2 (bis(dibenzylideneacetonepalladium), 0.4 g of a 10% by weight tri-tert-butylphosphine toluene solution (the amount of tri-tert-butylphosphine was 0.0002 mol), and 0.03 mol of sodium tert-butoxide. The mixture was heated to reflux for 12 h, 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 recrystallized from ethanol to obtain intermediate 18-0.

[0100] The intermediate 18-0 was subjected to mass spectrometry detection, and the mass-to-charge ratio (m / z) was measured to be 537.3.

[0101] (2) Synthesis of Compound 18

[0102] Referring to the synthesis method of Synthesis Example 3, the diamine-2 in Synthesis Example was replaced with an equal molar amount of Intermediate 18-0, and other conditions remained unchanged to obtain Compound 18;

[0103] Compound 18 was detected by mass spectrometry, and the mass-to-charge ratio (m / z) was measured to be 1295.7.

[0104] Referring to the synthesis methods of the above compounds and combining common organic synthesis methods, compounds 23, 26, 32, 44, 50, 59 and 71 were prepared and subjected to mass spectrometry detection. The test results are shown in Table 1 below.

[0105] Table 1

[0106]

[0107]

[0108]

[0109] Other compounds for which specific synthesis steps are not listed can be prepared by common knowledge in the art in combination with the above examples.

[0110] The specific structures of the compounds used in the following device examples and device comparative examples are shown below:

[0111]

[0112] In the following device examples, the boron-nitrogen-containing compound provided by the present invention is selected as the dopant material for the light-emitting layer of the organic electroluminescent device. In the device comparative examples, the above-mentioned BD-1 and BD-2 are selected as the dopant material for the light-emitting layer of the organic electroluminescent device.

[0113] Device Example 1

[0114] This device embodiment provides an organic electroluminescent device, using the compound 5 provided in Synthesis Example 1 of the present invention as a doping material for the light-emitting layer; and in this embodiment, the light-emitting layer is prepared by evaporation.

[0115] The structure of the organic electroluminescent device is:

[0116] ITO / HT (40 nm) / BH: Compound 5 (3%) / TPBI (30 nm) / LiF (0.5 nm) / Al (150 nm).

[0117] The preparation method of the organic electroluminescent device is as follows:

[0118] A glass substrate coated with an ITO transparent conductive layer (as an anode) was ultrasonically treated in a cleaning agent, then rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol, and baked in a clean environment until the water was completely removed. The substrate was then cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam to improve the surface properties and enhance its binding ability with the hole injection layer.

[0119] The glass substrate was placed in a vacuum chamber and evacuated to 1×10 -5 ~9×10 -6 Pa, HT was vacuum evaporated on the anode as a hole transport layer with an evaporation rate of 0.1 nm / s and a film thickness of 40 nm;

[0120] The light-emitting layer was vacuum-deposited on the hole transport layer at a deposition rate of 0.1 nm / s and a total deposition thickness of 30 nm. The main material of the light-emitting layer was BH, and the doping material was compound 5 provided by the present invention. 3% refers to the doping ratio of the doping material, that is, the volume ratio of the main material of the light-emitting layer to the doping material was 97:3.

[0121] The glass substrate with the light-emitting layer deposited in the previous step was transferred to a vacuum chamber, and TPBI was vacuum-deposited on the light-emitting layer as the electron transport layer of the device at a deposition rate of 0.1 nm / s and a total deposition thickness of 30 nm.

[0122] 0.5 nm of LiF and 150 nm of Al were vacuum-deposited on the electron transport layer to serve as the electron injection layer and cathode.

[0123] The brightness, driving voltage and current efficiency of the prepared organic electroluminescent devices were measured.

[0124] Device Examples 2 to 11

[0125] Device Examples 2 to 11 each provide an organic electroluminescent device, which differs from Device Example 1 only in that the doping materials of the light-emitting layer are different (see Table 2 for details), and other conditions are the same as those of Device Example 1.

[0126] Device Comparative Examples 1-2

[0127] Device Comparative Examples 1 and 2 respectively provide an organic electroluminescent device, which differs from Device Example 1 only in that the doping materials of the light-emitting layer are different (see Table 2 for details), and other conditions are the same as those of Device Example 1.

[0128] Performance Testing

[0129] Test the driving voltage, current efficiency and lifespan LT90 of the OLED devices provided above; LT90 refers to the time required for the brightness to drop to 90% of the original brightness while maintaining the current density at an initial brightness of 1000 nit. The test items include the brightness, driving voltage, and current efficiency of the organic electroluminescent device. The driving voltage, current efficiency, and LT90 data are all based on a brightness of 1000 cd / m 2 The relative values ​​of BD-1 and BD-2 are shown in Table 2 below.

[0130] Table 2

[0131] Doping materials <![CDATA[Required brightness / (cd / m 2 )]]> Driving voltage Current efficiency LT90 lifespan Device Comparative Example 1 BD-1 1000 1 1 1 Device Comparative Example 2 BD-2 1000 1.05 0.93 0.91 Device Example 1 Compound 5 1000 0.89 1.24 1.28 Device Example 2 Compound 12 1000 0.78 1.27 1.25 Device Example 3 Compound 16 1000 0.88 1.24 1.36 Device Example 4 Compound 18 1000 0.81 1.31 1.33 Device Example 5 Compound 23 1000 0.82 1.26 1.24 Device Example 6 Compound 26 1000 0.85 1.32 1.33 Device Example 7 Compound 32 1000 0.76 1.37 1.24 Device Example 8 Compound 44 1000 0.78 1.25 1.29 Device Example 9 Compound 50 1000 0.77 1.35 1.42 Device Example 10 Compound 59 1000 0.83 1.32 1.36 Device Example 11 Compound 71 1000 0.79 1.33 1.38

[0132] As can be seen from the above, the present invention obtains a compound suitable for use as a doping material for the light-emitting layer through structural design, and the organic electroluminescent device prepared thereby has a lower driving voltage, higher current efficiency and longer service life.

[0133] The applicant declares that while the above-described embodiments illustrate the boron-nitrogen compounds and their applications, the present invention is not limited to these embodiments, nor does it necessarily rely on these embodiments for implementation. Those skilled in the art will appreciate that any improvements to the present invention, equivalent substitutions for raw materials in the products of the present invention, additions of auxiliary ingredients, and selection of specific methods, etc., fall within the scope of protection and disclosure of the present invention.

Claims

1. A boron-nitrogen compound containing pyridine and carbazole, characterized in that: The boron nitrogen compound containing pyridine and carbazole has a structure as shown in Formula I: X is selected from oxygen, sulfur or Where * represents the attachment site of the group; In Formula I, R1, R2, R3, R4, R5, R6, and R7 are the same or different from each other and are independently selected from hydrogen, deuterium, substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C3~C 30 heteroaryl; Ar1, Ar2 and Ar3 are each independently selected from substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C3~C 30 heteroaryl; When the substituted or unsubstituted group contains a substituent, the substituent is selected from deuterium, F, CN, C1-C 12 Alkyl, C6~C 30 Aryl or C3~C 30 heteroaryl; All hydrogen atoms in formula I can be independently replaced by deuterium, F, CN, C1-C 12 Alkyl, C6~C 30 Aryl or C3~C 30 is substituted with a heteroaryl group.

2. The boron-nitrogen compound according to claim 1, characterized in that The C1~C 12 The alkyl group is selected from methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, tert-pentyl, n-hexyl or cyclohexyl.

3. The boron-nitrogen compound according to claim 1, characterized in that The C6~C 30 The aryl group of is selected from phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, indenyl, fluorenyl, perylenyl, phenanthrenyl, pyrenyl, fluoranthenyl, fluorenyl, spirobifluorenyl or triphenylenyl.

4. The boron-nitrogen-containing compound according to claim 1, characterized in that The C3~C 30 The heteroatoms in the heteroaryl group are selected from oxygen, sulfur, nitrogen or silicon.

5. The boron-nitrogen compound according to claim 1 and claim 4, characterized in that: The C3~C 30 The heteroaromatic group is selected from benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, diarylideneamine, benzofuranocarbazolyl, benzofuranothiophenyl or triazine.

6. The boron-nitrogen-containing compound according to claim 1, characterized in that R1, R2, R3, R4, R5, R6, R7 are the same as or different from each other and are each independently selected from hydrogen, deuterium, methyl, tert-butyl, phenyl, The wavy lines represent the attachment sites of the groups; Preferably, Ar1, Ar2 and Ar3 are each independently selected from phenyl, biphenyl, 7. The boron-nitrogen compound according to any one of claims 1 to 6, characterized in that The boron-nitrogen compound is selected from any one of compounds 1 to 72:

8. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises the boron nitrogen compound according to any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, characterized in that: The organic electroluminescent device comprises a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode; the organic layer comprises a light-emitting layer; the light-emitting layer comprises the boron-nitrogen compound according to any one of claims 1 to 7; Preferably, the light-emitting layer is prepared by evaporation.

10. A display device, characterized in that: The display device comprises the organic electroluminescent device according to claim 8 or 9.

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