A boron-nitrogen compound and an organic electroluminescent device comprising the same

Abstract

The present application relates to the technical field of organic photoelectric material preparation, and particularly relates to a boron-nitrogen compound and an organic electroluminescent device containing the same. The boron-nitrogen compound has good electron and hole receiving capacity, and the interaction between light-emitting molecules can be effectively inhibited by introducing a boron-containing spiro ring group with large steric hindrance. Specifically, the current efficiency of the organic electroluminescent device prepared by using the boron-nitrogen compound as a functional layer, especially as a light-emitting layer, is improved, and the efficiency and service life of the device are greatly improved. It is shown that most of the electrons and holes are combined, and the energy is effectively transferred to the boron-nitrogen compound, thereby realizing high light-emitting efficiency.

Description

Technical Field

[0001] This invention relates to the field of organic optoelectronic material preparation technology, specifically to a boron nitride compound and an organic electroluminescent device containing the same. Background Technology

[0002] With the development of multimedia technology and the increasing demands for information technology, the requirements for panel display performance are becoming increasingly stringent. Among these, OLEDs, with their advantages of self-emissive emission, low-voltage DC drive, full solid-state operation, wide viewing angle, and rich colors, have attracted widespread attention due to their potential applications in next-generation displays and lighting technologies, showing a very broad application prospect. Organic electroluminescent devices are self-emissive light-emitting devices. The light-emitting mechanism of OLEDs involves electrons and holes being injected from the positive and negative electrodes respectively under the action of an external electric field, migrating, recombinating, and decaying in the organic material to produce light. A typical OLED structure includes one or more functional layers such as a cathode layer, anode layer, electron injection layer, electron transport layer, hole blocking layer, hole transport layer, hole injection layer, and light-emitting layer. Although research on organic electroluminescence has progressed very rapidly, many problems still need to be solved. For example, the development of efficient, long-lifetime, narrow-emission green light materials remains a pressing issue for those skilled in the art. Summary of the Invention

[0003] The purpose of this invention is to address the shortcomings of existing technologies by providing a boron-nitrogen compound and an organic electroluminescent device containing the same. This invention effectively suppresses the interactions between luminescent molecules by introducing a sterically hindered double-spirocyclic group. Simultaneously, by introducing a rigid boron-containing spirocyclic structure to optimize the electron and hole reception capabilities of the boron-nitrogen compound, the energy transfer performance between the host and guest molecules can be improved, and the concentration of high-energy excitons in the luminescent layer can be reduced, thereby achieving a highly efficient, long-lifetime, narrow-emission green light material.

[0004] To achieve the objectives of this invention, the technical solution is as follows:

[0005] According to one or more embodiments, the present invention provides a boron nitride compound having the general formula structure shown in Formula I below;

[0006] ;

[0007] In Formula I, R1-R9 are monosubstituted or polysubstituted; each of R1-R9 is independently selected from one or more of hydrogen, deuterium, halogen, C1-C24 alkyl, substituted or unsubstituted C3-C24 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, phenoxy, and phenylthio; adjacent substituents R7 and R8 can be selectively linked to form a ring;

[0008] X1 and X2 are each independently selected from non-existent CR10 R 11 NR 12 ,O,S or Se,R 10 R 11 R 12 Each is independently selected from C1-C24 alkyl, substituted or unsubstituted C6-C30 aryl;

[0009] When a substitution is present, the substitution is selected from one or more of deuterium, halogen, C1-C12 alkyl, and C6-C18 aryl.

[0010] Preferably, the boron-nitrogen compound has the following general formula structure:

[0011]

[0012] In formulas Ia-Ij, R1-R9 are monosubstituted or polysubstituted, and each of R1-R9 is independently selected from one or more of hydrogen, deuterium, C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C5-C18 heteroaryl, phenoxy, and phenylthio; each of R is independently selected from hydrogen, deuterium, and C1-C12 alkyl, and adjacent substituents R7 and R8 can be selectively linked to form a ring; when substituted, the substituted is selected from one or more of deuterium, F, methyl, ethyl, propyl, and tert-butyl.

[0013] Preferably, when R7 and R8 in Formula I are selectively connected to form a ring, the following general structure is formed:

[0014] ;

[0015] In formula I-1 or I-2, the substitution of R1-R6, X1, and X2 is as defined in formula I; R9 is independently selected from hydrogen, deuterium, C1-C12 alkyl, C6-C30 aryl groups substituted or unsubstituted with C1-C12 alkyl, and R 13 Independently selected from hydrogen, deuterium, C1-C12 alkyl; or R9 and R 13 Connect them into the following structure, where * indicates a connection point:

[0016] ;

[0017] Each Ra is independently selected from hydrogen, deuterium, or C1-C12 alkyl groups.

[0018] More preferably, Ra is selected independently from hydrogen, deuterium or tert-butyl each time it appears.

[0019] Preferably, R1-R9 are monosubstituted, disubstituted, or maximally substituted, and each of R1-R9 is independently selected from one or more of hydrogen, deuterium, F, methyl, ethyl, propyl, tert-butyl, pentyl, phenyl, methylphenyl, tert-butylphenyl, diphenyl, tert-phenyl, naphthyl, anthracene, phenanthryl, pyridyl, quinolinyl, phenoxy, phenylthio, furanyl, thiophene, benzofuranyl, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, tert-butyl-substituted carbazoyl, 9,9-dimethylfluorenyl, and phenyl-substituted amino groups.

[0020] The substituents may be further replaced by deuterium or F.

[0021] According to one or more embodiments, the present invention provides a specific boron-nitrogen compound selected from any of the following chemical structures, wherein "D" represents deuterium:

[0022]

[0023] According to one or more embodiments, the present invention also provides the use of boron nitride compounds with the general structure shown in Formula I above in the preparation of electronic devices.

[0024] Furthermore, the electronic devices include organic light-emitting diodes (OLEDs), organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optoelectronic devices, organic optical detectors, organic photosensors, organic field quenching devices (O-FQDs), light-emitting electrochemical cells (LECs), and organic laser diodes (O-lasers).

[0025] According to one or more embodiments, the present invention also provides an organic electroluminescent device, the organic electroluminescent device comprising a cathode, an anode, and an organic functional layer therebetween; the organic functional layer further comprising a light-emitting layer, the light-emitting layer comprising a boron-nitrogen compound with the general structure shown in Formula I above. The mass percentage of the boron-nitrogen compound is between 0.1% and 50%.

[0026] According to one or more embodiments, the present invention also provides an organic optoelectronic device, comprising a first electrode; a second electrode facing the first electrode; and a light-emitting material layer disposed between the first electrode and the second electrode, wherein the light-emitting material layer comprises a boron nitride compound with a general structure as shown in Formula I above. For example, the boron nitride compound may be included as a dopant in the light-emitting material layer.

[0027] The present invention also provides a composition comprising a boron nitrogen compound having the general structure shown in Formula I above.

[0028] The present invention also provides a formulation comprising a boron-nitrogen compound with the general structure shown in Formula I above and at least one solvent. The solvent is not particularly limited and may be any solvent well known to those skilled in the art, such as unsaturated hydrocarbon solvents, halogenated saturated hydrocarbon solvents, halogenated unsaturated hydrocarbon solvents, ether solvents, or ester solvents; wherein the unsaturated hydrocarbon solvent is toluene, xylene, mesitylene, tetrahydronaphthalene, n-butylbenzene, sec-butylbenzene, or tert-butylbenzene; the halogenated saturated hydrocarbon solvent is carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, or bromocyclohexane; the halogenated unsaturated hydrocarbon solvent is chlorobenzene, dichlorobenzene, or trichlorobenzene; the ether solvent is tetrahydrofuran or tetrahydropyran; and the ester solvent is an alkyl benzoate ester.

[0029] The present invention also provides a display or lighting device comprising one or more of the organic electroluminescent devices or organic optoelectronic devices as described above.

[0030] Compared with the prior art, the beneficial effects of the present invention are:

[0031] This invention provides a boron nitride compound with excellent electron and hole accepting capabilities. By introducing a sterically hindered boron-containing spirocyclic ring and substituted spirocyclic groups, the aggregation quenching effect between luminescent molecules can be effectively suppressed. The rigid spirocyclic structure and conjugated substituents enable the compound to suppress nonradiative transitions while enhancing energy transfer performance between the host and guest (or sensitizer). Specifically, organic electroluminescent devices fabricated using the boron nitride compound of this invention as a functional layer, especially as a luminescent layer, exhibit significantly improved current efficiency and device lifetime. This demonstrates that after most electrons and holes recombine, energy is effectively transferred to the boron nitride compound, thereby achieving high luminous efficiency. Detailed Implementation

[0032] The present invention will now be described in detail. The descriptions of the constituent elements described below are sometimes based on representative embodiments or specific examples of the invention, but the invention is not limited to such embodiments or specific examples. This disclosure can be more readily understood by referring to the following detailed descriptions and the examples contained therein. Before disclosing and describing the compounds, devices, and / or methods of the present invention, it should be understood that, unless otherwise stated, they are not limited to specific synthetic methods or specific reagents, as these can vary. It should also be understood that the terminology used in this invention is for describing particular aspects only and is not intended to be limiting. Although any similar or equivalent methods and materials described in this invention can be used in this practice or experiment, exemplary methods and materials are now described.

[0033] In this invention, "alkyl" refers to a monovalent alkyl group having 1-24 carbon atoms, preferably 1-12 carbon atoms, and more preferably 1-6 carbon atoms. Examples of this term include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-hexyl, etc.

[0034] The term "cycloalkyl" as used in this invention refers to a cyclic alkyl group having 3-24 carbon atoms and one monocyclic or polycyclic fused ring, preferably 3-14 carbon atoms, which can be arbitrarily substituted by 1-3 alkyl groups. Such cycloalkyl groups include, for example, monocyclic structures such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexane, cyclooctyl, 1-methylcyclopropyl, 2-methylcyclopentyl, 2-methylcyclooctyl, methylcyclohexane, etc., or polycyclic structures such as adamantyl.

[0035] The term "aryl" as used in this invention refers to an unsaturated aromatic carbon ring having 6-30 carbon atoms and being a monocyclic (e.g., phenyl) or polycyclic fused (e.g., naphthyl or anthracene) ring, preferably having 6-18 carbon atoms, more preferably 1-12 carbon atoms. Preferred aryl groups include phenyl, biphenyl, naphthyl, phenanthryl, terphenyl, etc. Unless otherwise defined for individual substituents, such aryl groups may optionally be substituted with 1-3 of the following substituents: hydroxyl, acyl, acyloxy, alkyl, alkoxy, alkenyl, alkynyl, amino, aminoacyl, aryl, aryloxy, carboxyl, carboxyl ester, aminocarboxyl ester, cyano, halogen, nitro, heteroaryl, heterocyclic, thioalkoxy, trihalomethyl, etc. Preferred substituents include alkyl, alkoxy, halogen, cyano, nitro, trihalomethyl, and thioalkoxy. However, this is not a limitation.

[0036] The term "heteroaryl" as used in this invention refers to a group consisting of 5-30 carbon atoms in a aryl group, where one or more aromatic carbon atoms are replaced by heteroatoms, preferably 5-18 carbon atoms. The heteroatoms include, but are not limited to, oxygen (O), sulfur (S) or nitrogen (N), silicon (Si) or cesium (Se) atoms. The heteroaryl group can be a monocyclic heteroaryl or a fused-ring heteroaryl group. Examples include pyridyl, pyrrole, pyridyl, thiophene, furanyl, indolyl, quinolinyl, isoquinolinyl, quinoxalinyl, benzothiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazole, etc., but are not limited thereto.

[0037] The substitution described in this invention can be achieved through single bonds or fusion. The "ring formation" described in this invention can include monocyclic, polycyclic, and fused rings, and the cyclic ring may be unsubstituted or substituted by one or more identical or different groups.

[0038] The singular forms of the terms “a,” “an,” and “the” used in the specification include plural references unless otherwise explicitly indicated by the context. Thus, for example, references to “component” include mixtures of two or more components.

[0039] Unless otherwise stated, all commercial reagents used in the following tests should be used directly after purchase.

[0040] In a preferred embodiment of the present invention, the OLED device of the present invention contains a hole transport layer. The hole transport material can preferably be selected from known or unknown materials, and is particularly preferably selected from the following structures (Ph is phenyl):

[0041] .

[0042] In a preferred embodiment of the present invention, the OLED device of the present invention includes a hole injection layer. The preferred hole injection layer material of the present invention has the following structure, but this does not mean that the present invention is limited to the following structure:

[0043] .

[0044] In a preferred embodiment of the present invention, the electron transport layer may be selected from at least one of the following compounds, but this does not mean that the present invention is limited to the following structures:

[0045] .

[0046] The preparation method of the boron nitride compound (guest compound) and the luminescent properties of the device are explained in detail below with reference to the following embodiments. The molecular structural formulas of the relevant materials are shown below:

[0047]

[0048] Example 1: Synthesis of Compound 1

[0049]

[0050] (1) Synthesis of compounds 1-3: BuLi (0.5 mL, 1 mmol, 2 M in hexane) was slowly added to an anhydrous THF (50 mL) solution of compound 1-1 (711 mg, 1 mmol) at -78 °C. After reacting for 3 hours, compound 1-2 (436 mg, 1 mmol) was slowly added; the mixture was then allowed to react overnight at room temperature, and 1 mL of ice water was added. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3 × 100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the residue was dissolved in acetic acid (100 mL), followed by dropwise addition of concentrated hydrochloric acid (10 mL). The reaction system was refluxed overnight and then cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3 × 100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the crude product was purified by silica gel column chromatography using dichloromethane:petroleum ether = 1:5 as the eluent, yielding product 1-3 (378 mg, yield 36%). Mass spectrometry m / z: theoretical value 1050.70; measured value M+H: 1051.74.

[0051] (2) Synthesis of compounds 1-4: Compound 1-3 (1051 mg, 1 mmol) was slowly added to 100 mL of a mixed solvent of glacial acetic acid / chloroform (1:1, v:v) at 0 °C, followed by slow addition of NBS (178 mg, 1 mmol). The mixture was stirred at 0 °C for 18 hours. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3 × 100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the crude product was purified by silica gel chromatography with dichloromethane:petroleum ether = 1:5 as the eluent to obtain product 1-4 (598 mg, yield 53%). Mass spectrometry m / z: theoretical value 1128.61; measured value M+H: 1129.67;

[0052] (3) Synthesis of Compound 1: Under a nitrogen atmosphere and at 0°C, tert-butyllithium (1.25 mL, 1.6 M pentane solution, 2 mmol) was slowly added dropwise to a tert-butylbenzene (100 mL) solution of Compounds 1-4 (1130 mg, 1 mmol). After reacting at 60°C for 4 hours, the system was cooled to -50°C, and then BBr3 (500 mg, 2 mmol) was added. After reacting at room temperature for 1 hour, N,N-diisopropylethylamine (259 mg, 2 mmol) was added. The system was then heated to 120°C and reacted for 12 hours. After cooling to room temperature, 5 mL of sodium acetate aqueous solution (1 M) was added. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3 × 100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the crude product was purified by silica gel column chromatography using dichloromethane:petroleum ether = 1:5 as the eluent, yielding product 1 (241 mg, yield 23%). Mass spectrometry m / z: theoretical value 1058.68; measured value M+H: 1059.71.

[0053] Example 2: Synthesis of Compound 124

[0054]

[0055] (1) Synthesis of compound 124-3: Compound 124-3 was synthesized according to the preparation scheme of compound 1-3 (yield 39%). Mass spectrometry m / z, theoretical value 872.37; measured value M+H: 873.42;

[0056] (2) Synthesis of compound 124-5: Compound 124-5 was synthesized according to the preparation scheme of compound 1-3 (yield 45%). Mass spectrometry m / z, theoretical value 1212.74; measured value M+H: 1213.77;

[0057] (3) Synthesis of compound 124-6: Compound 124-6 was synthesized according to the preparation scheme of compound 1-4 (yield 61%). Mass spectrometry m / z, theoretical value 1290.65; measured value M+H: 1291.68;

[0058] (4) Synthesis of compound 124: Compound 124 was synthesized according to the preparation scheme of compound 1 (yield 27%). Mass spectrometry m / z, theoretical value 1220.73; measured value M+H: 1221.75.

[0059] Example 3: Synthesis of Compound 2

[0060] Compound 2 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 25%. Mass spectrometry m / z: theoretical value 970.56; measured value M+H: 971.59.

[0061] Example 4: Synthesis of Compound 3

[0062] Compound 3 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 23%. Mass spectrometry m / z: theoretical value 918.45; measured value M+H: 919.49.

[0063] Example 5; Synthesis of Compound 4

[0064] Compound 4 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 26%. Mass spectrometry m / z: theoretical value 950.41; measured value M+H: 951.46.

[0065] Example 6: Synthesis of Compound 8

[0066] Compound 8 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 24%. Mass spectrometry m / z: theoretical value 1178.68; measured value M+H: 1179.73.

[0067] Example 7: Synthesis of Compound 15

[0068] Compound 15 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 23%. Mass spectrometry m / z: theoretical value 1152.58; measured value M+H: 1153.61.

[0069] Example 8: Synthesis of Compound 17

[0070] Compound 17 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 26%. Mass spectrometry m / z: theoretical value 1247.74; measured value M+H: 1248.79.

[0071] Example 9: Synthesis of Compound 20

[0072] Compound 20 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 28%. Mass spectrometry m / z: theoretical value 1078.56; measured value M+H: 1079.60.

[0073] Example 10: Synthesis of Compound 22

[0074] Compound 22 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 23%. Mass spectrometry m / z: theoretical value 1105.63; measured value M+H: 1106.65.

[0075] Example 11: Synthesis of Compound 25

[0076] Compound 25 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 21%. Mass spectrometry m / z: theoretical value 1121.60; measured value M+H: 1122.65.

[0077] Example 12: Synthesis of Compound 26

[0078] Compound 26 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 25%. Mass spectrometry m / z: theoretical value 1169.55; measured value M+H: 1170.58.

[0079] Example 13: Synthesis of Compound 34

[0080] Compound 34 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 22%. Mass spectrometry m / z: theoretical value 1247.74; measured value M+H: 1248.78.

[0081] Example 14: Synthesis of Compound 36

[0082] Compound 36 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 27%. Mass spectrometry m / z: theoretical value 1094.46; measured value M+H: 1095.49.

[0083] Example 15: Synthesis of Compound 39

[0084] Compound 39 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 25%. Mass spectrometry m / z: theoretical value 1102.65; measured value M+H: 1103.71.

[0085] Example 16: Synthesis of Compound 52

[0086] Compound 52 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 29%. Mass spectrometry m / z: theoretical value 1122.59; measured value M+H: 1123.64.

[0087] Example 17: Synthesis of Compound 56

[0088] Compound 56 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 24%. Mass spectrometry m / z: theoretical value 1128.67; measured value M+H: 1129.71.

[0089] Example 18: Synthesis of Compound 61

[0090] Compound 61 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 23%. Mass spectrometry m / z: theoretical value 1204.70; measured value M+H: 1205.73.

[0091] Example 19: Synthesis of Compound 63

[0092] Compound 63 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 26%. Mass spectrometry m / z: theoretical value 1294.71; measured value M+H: 1295.74.

[0093] Example 20: Synthesis of Compound 73

[0094] Compound 73 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 23%. Mass spectrometry m / z: theoretical value 1220.69; measured value M+H: 1221.71.

[0095] Example 21: Synthesis of Compound 77

[0096] Compound 77 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 28%. Mass spectrometry m / z: theoretical value 1288.72; measured value M+H: 1289.76.

[0097] Example 22: Synthesis of Compound 81

[0098] Compound 81 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 29%. Mass spectrometry m / z: theoretical value 1286.78; measured value M+H: 1287.80.

[0099] Example 23: Synthesis of Compound 100

[0100] Compound 100 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 25%. Mass spectrometry m / z: theoretical value 1254.71; measured value M+H: 1255.76.

[0101] Example 24: Synthesis of Compound 101

[0102] Compound 101 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 23%. Mass spectrometry m / z: theoretical value 1289.79; measured value M+H: 1290.82.

[0103] Example 25: Synthesis of Compound 105

[0104] Compound 105 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 21%. Mass spectrometry m / z: theoretical value 1314.81; measured value M+H: 1315.84.

[0105] Example 26: Synthesis of Compound 108

[0106] Compound 108 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 25%. Mass spectrometry m / z: theoretical value 1122.62; measured value M+H: 1123.64.

[0107] Example 27: Synthesis of Compound 109

[0108] Compound 109 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 23%. Mass spectrometry m / z: theoretical value 980.54; measured value M+H: 981.58.

[0109] Example 28: Synthesis of Compound 119

[0110] Compound 119 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 28%. Mass spectrometry m / z: theoretical value 1304.73; measured value M+H: 1305.76.

[0111] Example 29: Synthesis of Compound 122

[0112] Compound 122 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 22%. Mass spectrometry m / z: theoretical value 1300.72; measured value M+H: 1301.77.

[0113] Example 30: Synthesis of Compound 123

[0114] Compound 123 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 25%. Mass spectrometry m / z: theoretical value 1244.73; measured value M+H: 1245.78.

[0115] Example 31: Synthesis of Compound 125

[0116] Compound 125 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 24%. Mass spectrometry m / z: theoretical value 1264.70; measured value M+H: 1265.75.

[0117] Example 32: Synthesis of Compound 128

[0118] Compound 128 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 22%. Mass spectrometry m / z: theoretical value 1270.75; measured value M+H: 1271.78.

[0119] Example 33: Synthesis of Compound 131

[0120] Compound 131 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 23%. Mass spectrometry m / z: theoretical value 1238.68; measured value M+H: 1239.71.

[0121] Example 34: Synthesis of Compound 135

[0122] Compound 135 was prepared according to the preparation schemes of Examples 1-2. The yield of the final product was 21%. Mass spectrometry m / z: theoretical value 1316.73; measured value M+H: 1317.76.

[0123] Manufacturing of OLED devices:

[0124] As a reference fabrication method for a device embodiment, the present invention involves depositing p-doped material on the surface or anode of an ITO glass with a light-emitting area of ​​2 mm × 2 mm, or co-evaporating the p-doped material with a hole transport material at a concentration of 1% to 50% to form a hole injection layer (HIL) of 5-100 nm. A hole transport layer (HTL) of 5-200 nm is then formed on the hole injection layer. Next, a light-emitting layer (EML) of 10-100 nm is formed on the hole transport layer by co-evaporating the host material (GH-1 and GH-2), GD-Ir, and the boron nitride compound (guest material) prepared in the present invention at a mass ratio of 66:30:3:1. Finally, a 35 nm electron transport layer (ETL) is formed by co-evaporating the host material. Then, a cathode of 70 nm is deposited to form an organic light-emitting diode.

[0125] In a preferred embodiment, the structure of the bottom-emitting OLED device provided by the present invention is as follows: a glass containing ITO is used as the anode, and HIL is deposited sequentially as follows: HT-1:P-3 (mass ratio 97:3) with a thickness of 10 nm; HTL is HT-2 with a thickness of 60 nm; EBL is HT-11 with a thickness of 20 nm; EML is the host material (GH-1:GH-2):GD-Ir: the boron nitride compound 1 provided by the present invention (mass ratio 66:30:3:1) with a thickness of 35 nm; ETL is ET-6:LiQ (mass ratio 50:50) with a thickness of 35 nm; EIL is a 1 nm LiF layer; then the cathode Al is deposited to a thickness of 70 nm to prepare an organic light-emitting diode, referred to as Application Example 1.

[0126] Referring to the device structure provided in Application Example 1, boron nitride compounds listed in Table 1 were selected as substitutes for Compound 1 to prepare organic light-emitting diodes, referred to as Application Examples 2 to 34 and Comparative Examples 1-3, respectively. The current efficiency and lifetime characteristics of the prepared devices in the application examples and comparative examples were tested using standard methods, and the device luminescence characteristics are shown in Table 1.

[0127] Table 1. Data on the light emission characteristics of the device

[0128]

[0129] As shown in Table 1, the compounds of this invention, when used as light-emitting layer materials in electronic devices, exhibit higher current efficiency and lifetime. Compared to Comparative Examples 1-3, Application Examples 1 to 34 demonstrate superior device performance in both current efficiency and lifetime. These performance improvements are attributed to the superior electron transport capabilities of the boron nitride compound materials of this invention. This indicates that the boron nitride compounds provided by this invention have significant commercial application value.

[0130] The above description is only a preferred embodiment of the present invention, but the scope of protection of the present invention is not limited thereto. Any equivalent substitutions or modifications made by those skilled in the art within the scope of the technology disclosed in the present invention, based on the technical solution and inventive concept of the present invention, should be covered within the scope of protection of the present invention.

Claims

1. A boron-nitrogen compound, characterized in that, The boron-nitrogen compound has the general formula shown in Formula I: In Formula I, R1-R3, R6, and R9 are monosubstituted or polysubstituted; R1 is independently selected from one or more of hydrogen, deuterium, halogen, C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C5-C18 heteroaryl, phenoxy, and phenylthio; R2-R3 are each independently selected from one or more of hydrogen, deuterium, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C5-C18 heteroaryl, phenoxy, and phenylthio; R4-R5 are each independently selected from C1-C12 alkyl; R6 is independently selected from C1-C12 alkyl and C6-C18 aryl; R7-R8 are each independently selected from C1-C12 alkyl and substituted or unsubstituted C6-C18 aryl; R9 is independently selected from hydrogen, deuterium, and substituted or unsubstituted C6-C18 aryl. X1 and X2 are each independently selected from non-existent CR 10 R 11 NR 12 ,O,S or Se,R 10 R 11 R 12 Each is independently selected from C1 to C24 alkyl, substituted or unsubstituted C6 to C30 aryl; when substituted, the substituted is selected from one or more of deuterium and C1 to C12 alkyl.

2. The boron-nitrogen compound according to claim 1, characterized in that, The boron-nitrogen compound has the following general formula structure: In formulas Ia-Ij, the substitution of R1-R9 is as defined in formula I; each R is independently selected from hydrogen, deuterium, and C1-C12 alkyl groups.

3. The boron-nitrogen compound according to claim 1, characterized in that, R1-R3 and R6 are monosubstituted, disubstituted, or maximally substituted, and R9 is monosubstituted or disubstituted; R1 is independently selected from one or more of hydrogen, deuterium, F, methyl, ethyl, propyl, tert-butyl, phenyl, methylphenyl, tert-butylphenyl, diphenyl, naphthyl, anthracene, phenanthryl, pyridyl, phenoxy, phenylthio, dibenzofuranyl, dibenzothiophene, carbazolyl, and tert-butyl-substituted carbazolyl; R2-R3 are each independently selected from one or more of hydrogen, phenyl, tert-butylphenyl, pyridyl, phenoxy, phenylthio, tert-butyl-substituted or unsubstituted carbazolyl; R4-R5 are each independently selected from methyl, ethyl, propyl, and tert-butyl; R6 is independently selected from methyl, ethyl, propyl, tert-butyl, and phenyl; R7-R8 are each independently selected from phenyl and tert-butylphenyl; and R9 is independently selected from hydrogen.

4. A boron-nitrogen compound, characterized in that, The boron-nitrogen compound has the following general formula: In Formula I-2, R1-R3, R6, and R9 are monosubstituted or polysubstituted; R1 is independently selected from one or more of hydrogen, deuterium, halogen, C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C5-C18 heteroaryl, phenoxy, and phenylthio; R2-R3 are each independently selected from one or more of hydrogen, deuterium, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C5-C18 heteroaryl, phenoxy, and phenylthio; R4-R5 are each independently selected from C1-C12 alkyl; R6 is independently selected from C1-C12 alkyl and C6-C18 aryl; R9 is independently selected from hydrogen and deuterium. X1 and X2 are each independently selected from non-existent CR 10 R 11 NR 12 ,O,S or Se,R 10 R 11 R 12 Each is independently selected from C1 to C24 alkyl, substituted or unsubstituted C6 to C30 aryl; when substituted, the substituted is selected from one or more of deuterium and C1 to C12 alkyl.

5. A boron-nitrogen compound, characterized in that, The boron-nitrogen compound has the following general formula: In Formula I-1, R1-R3, R6, and R9 are monosubstituted or polysubstituted; R1 is independently selected from one or more of hydrogen, deuterium, halogen, C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C5-C18 heteroaryl, phenoxy, and phenylthio; R2-R3 are each independently selected from one or more of hydrogen, deuterium, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C5-C18 heteroaryl, phenoxy, and phenylthio; R4-R5 are each independently selected from C1-C12 alkyl; R6 is independently selected from C1-C12 alkyl and C6-C18 aryl; X1 and X2 are each independently selected from those that do not exist, CR 10 R 11 NR 12 ,O,S or Se,R 10 R 11 R 12 Each of the following is independently selected from C1-C24 alkyl, substituted or unsubstituted C6-C30 aryl; when substituted, the substituted element is selected from one or more of deuterium and C1-C12 alkyl; R9 is independently selected from hydrogen, deuterium, C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl, R 13 Independently selected from hydrogen, deuterium, C1-C12 alkyl; or R9 and R 13 Connect them into the following structure, where * indicates a connection point: Each Ra is independently selected from hydrogen, deuterium, or C1-C12 alkyl groups.

6. A boron-nitrogen compound, characterized in that, The boron-nitrogen compound is selected from any of the following chemical structures, where "D" represents deuterium:

7. The use of the boron nitride compound according to any one of claims 1-6 in the preparation of electronic devices.

8. The application according to claim 7, characterized in that, The electronic device is an organic electroluminescent device.

9. The application according to claim 7, characterized in that, The electronic device is an organic optoelectronic device.

10. An organic electroluminescent device, characterized in that, The organic electroluminescent device comprises a cathode, an anode, and an organic functional layer between the two; the organic functional layer includes a light-emitting layer, which contains a boron-nitrogen compound as described in any one of claims 1-6.

11. An organic optoelectronic device, characterized in that, The organic optoelectronic device includes a first electrode, a second electrode facing the first electrode, and a light-emitting material layer disposed between the first electrode and the second electrode; the light-emitting material layer contains a boron nitrogen compound as described in any one of claims 1-6.

12. A composition, characterized in that, The composition comprises a boron nitrogen compound as described in any one of claims 1-6.

13. A formulation, characterized in that, The formulation comprises a boron nitrogen compound as described in any one of claims 1-6 and at least one solvent.

14. A display or lighting device, characterized in that, The device comprises one or more of the organic electroluminescent device of claim 10 and / or the organic optoelectronic device of claim 11.

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