Boron-nitrogen compound, organic light-emitting device comprising same and application of boron-nitrogen compound and organic light-emitting device

Abstract

The invention relates to the technical field of preparation of organic photoelectric materials, in particular to a boron-nitrogen compound, an organic light-emitting device comprising the same and application of the boron-nitrogen compound and the organic light-emitting device. The boron-nitrogen compound disclosed by the invention has good electron and hole receiving capability, and close packing among luminescent molecules can be effectively inhibited by introducing a large-steric-hindrance spiro structure and asymmetric substituent groups on two acridine rings. Specifically, the boron-nitrogen compound provided by the invention is used as a functional layer, especially as an organic electroluminescent device manufactured by a luminescent layer, the current efficiency is improved, the efficiency of the device is greatly improved, and the service life of the device is greatly prolonged. It shows that after most electrons and holes are compounded, energy is effectively transmitted to the boron-nitrogen compound, and therefore higher luminous efficiency is achieved.

Description

Technical Field

[0001] This invention relates to the field of organic optoelectronic material preparation technology, specifically to a boron-nitrogen compound and organic electroluminescent devices containing the same, and their applications. 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. 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 close packing of luminescent molecules by introducing asymmetric substituent groups. Simultaneously, by introducing a rigid spirocyclic structure to optimize the electron and hole accepting 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: According to one or more embodiments, the present invention provides a boron-nitrogen compound having the general formula structure shown in Formula I: ; In Formula I, ring A is selected from one or more C5-C30 cycloalkyl groups, substituted or unsubstituted with Rn; Rn is independently represented as one or more of hydrogen, deuterium, halogen, cyano, C1-C10 alkyl, C3-C24 cycloalkyl, C2-C10 alkenyl, C2-C10 alkoxy, C6-C10 aryloxy, arylamino, C6-C30 aryl, and C5-C30 heteroaryl; Rn is substituted by a single bond or a fused ring, and Rn can be further substituted by deuterium, C1-C10 alkyl, or C6-C30 aryl. R1 and R2 are each selected from substituted or unsubstituted C3-C24 cycloalkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C5-C30 heteroaryl, whether identical or different. When R1 and R2 contain substitutions, each substitution is independently selected from deuterium, C1-C24 alkyl, C3-C24 cycloalkyl, C6-C30 aryl, or C5-C30 heteroaryl. R3-R6 are monosubstituted or polysubstituted. Each of R3-R6 is independently selected from deuterium, halogen, cyano, or C1-C24 alkyl.

[0005] Preferably, R1 and R2 are connected by only one carbon atom, with no other connection method.

[0006] Preferably, R1-R2 are each selected from one or more of the following groups, either substituted or unsubstituted: phenyl, biphenyl, naphthyl, tetrahydronaphthyl, anthracene, phenanthryl, pyridyl, quinolinyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, and diphenylamino; when substituted, the substituted group is monosubstituted, disubstituted, or has the maximum number of substituted groups, and each substituted group is independently selected from deuterium, F, methyl, ethyl, propyl, tert-butyl, phenyltert-butyl, and adamantyl.

[0007] Preferably, R3-R6 are each selected from methyl, ethyl, isopropyl, and tert-butyl.

[0008] Preferably, in Formula I, ring A is selected from adamantyl, norbornel, Rn-substituted or unsubstituted cyclopentyl, and Rn-substituted or unsubstituted cyclohexyl; each time Rn appears, Rn is independently selected from one or more of hydrogen, deuterium, F, cyano, C1-C10 alkyl, C3-C12 cycloalkyl, C6-C18 aryl, and C5-C18 heteroaryl.

[0009] More preferably, ring A in formula I is selected from the following structures: , Ra and Rb are monosubstituted or polysubstituted, and each time Ra and Rb are independently selected from one or more of hydrogen, deuterium, methyl, ethyl, propyl, tert-butyl, tert-butyl substituted or unsubstituted phenyl, and tert-butyl substituted or unsubstituted biphenyl.

[0010] 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: .

[0011] On the one hand, the present invention also provides the application of boron nitrogen compounds as shown in Formula I above in the preparation of electronic devices.

[0012] 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).

[0013] In another aspect, 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 as shown in Formula I above.

[0014] Furthermore, the boron-nitrogen compound has a mass percentage of 0.1%-50%.

[0015] In another aspect, 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 as shown in Formula I above. For example, the boron nitride compound may be included as a dopant in the light-emitting material layer.

[0016] The present invention also provides a composition comprising a boron nitrogen compound as shown in Formula I above.

[0017] The present invention also provides a formulation comprising a boron nitrogen compound as shown in Formula I above or a composition as described 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.

[0018] 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.

[0019] Compared with the prior art, the beneficial effects of the present invention are: This invention provides a boron nitride compound with excellent electron and hole accepting capabilities. By introducing a sterically hindered spirocyclic structure and asymmetric substituents on the two acridine rings, the close packing of luminescent molecules can be effectively suppressed. The rigid spirocyclic structure and conjugated substituents enable the compound to enhance the 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 higher luminous efficiency. Detailed Implementation

[0020] 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.

[0021] In this invention, "alkyl" refers to a monovalent alkyl group having 1-24 carbon atoms, preferably 1-14 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.

[0022] The term "cycloalkyl" as used in this invention refers to a cyclic alkyl group having 3-24 carbons and one monocyclic or polycyclic fused ring, preferably 3-14 carbons, which can be substituted by 1-3 alkyl groups in any way. 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.

[0023] The term "aryl" as used in this invention refers to an unsaturated aromatic carbon ring having 6-30 carbons and being a monocyclic (e.g., phenyl) or polycyclic fused (e.g., naphthyl or anthracene) ring, preferably having 6-18 carbons, more preferably 6-12 carbons. 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.

[0024] The term "heteroaryl" as used in this invention refers to a group obtained by heterosubstitution of one or more aromatic carbons in a group of 5-30 carboaryl groups, preferably 5-18 carbons. The heterosubstitution includes, but is not limited to, oxygen (O), sulfur (S) or nitrogen (N), silicon (Si) or germanium (Ge). The heteroaryl can be a monocyclic heteroaryl or a fused-ring heteroaryl. Examples include pyridyl, pyrrole, pyridyl, thiophene, furanyl, indolyl, quinolinyl, isoquinolinyl, quinoxalinyl, benzothiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, etc., but are not limited thereto.

[0025] 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.

[0026] 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.

[0027] Unless otherwise stated, all commercial reagents used in the following tests should be used directly after purchase.

[0028] 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): .

[0029] 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: .

[0030] 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: .

[0031] 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:

[0032] Example 1: Synthesis of Compound 1

[0033] 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 (788 mg, 1 mmol) at -78 °C. After 3 hours of reaction, 1-2 (294 mg, 1 mmol) was slowly added. The mixture was slowly brought to room temperature and reacted overnight, followed by the addition of 1 mL of ice water. 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 over 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 over 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 (427 mg, yield 43%). Mass spectrometry m / z: theoretical value 986.51; measured value M+H: 987.58.

[0034] Synthesis of compounds 1-5: Compounds 1-5 were synthesized using the same preparation scheme as compounds 1-3 (yield 53%). Mass spectrometry m / z: theoretical value 1070.65; measured value M+H: 1071.69.

[0035] Synthesis of compounds 1-6: Compounds 1-5 (1070 mg, 1 mmol) were slowly added to 100 mL of a glacial acetic acid / chloroform (1:1, v:v) mixed solvent at 0 °C, followed by the slow addition of NBS (178 mg, 1 mmol). The mixture was stirred at 0 °C for 24 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 over sodium sulfate. The solvent was removed by vacuum distillation, and the crude product was purified by silica gel column chromatography using dichloromethane:petroleum ether = 1:6 as the eluent to obtain product 1-6 (635 mg, 55% yield). Mass spectrometry m / z: theoretical value 1148.59; measured value M+H: 1149.62.

[0036] 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 1-6 (1148 mg, 1 mmol). The system was reacted at 60°C for 4 hours, then cooled to -50°C, and 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 temperature was then raised 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 over 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 to give Compound 1 (241 mg, yield 21%). Mass spectrometry m / z, theoretical value 1078.63; measured value M+H: 1079.68.

[0037] Example 2: Synthesis of Compound 3 Compound 3 was prepared according to the preparation scheme of Example 1. The yield of the final product was 26%. Mass spectrometry m / z: theoretical value 1128.65; measured value M+H: 1129.69.

[0038] Example 3: Synthesis of Compound 5 Compound 5 was prepared according to the preparation scheme of Example 1. The yield of the final product was 22%. Mass spectrometry m / z: theoretical value 1072.59; measured value M+H: 1073.65.

[0039] Example 4: Synthesis of Compound 6 Compound 6 was prepared according to the preparation scheme of Example 1. The yield of the final product was 25%. Mass spectrometry m / z: theoretical value 1190.76; measured value M+H: 1191.81.

[0040] Example 5: Synthesis of Compound 8 Compound 8 was prepared according to the preparation scheme of Example 1. The yield of the final product was 23%. Mass spectrometry m / z: theoretical value 1186.73; measured value M+H: 1187.77.

[0041] Example 6: Synthesis of Compound 12 Compound 12 was prepared according to the preparation scheme of Example 1. The yield of the final product was 24%. Mass spectrometry m / z: theoretical value 1210.73; measured value M+H: 1211.75.

[0042] Example 7: Synthesis of Compound 14 Compound 14 was prepared according to the preparation scheme of Example 1. The yield of the final product was 27%. Mass spectrometry m / z: theoretical value 1210.73; measured value M+H: 1211.77.

[0043] Example 8: Synthesis of Compound 18 Compound 18 was prepared according to the preparation scheme of Example 1. The yield of the final product was 24%. Mass spectrometry m / z: theoretical value 1234.73; measured value M+H: 1235.76.

[0044] Example 9: Synthesis of Compound 19 Compound 19 was prepared according to the preparation scheme of Example 1. The yield of the final product was 25%. Mass spectrometry m / z: theoretical value 1178.67; measured value M+H: 1179.71.

[0045] Example 10: Synthesis of Compound 20 Compound 20 was prepared according to the preparation scheme of Example 1. The yield of the final product was 22%. Mass spectrometry m / z: theoretical value 1242.70; measured value M+H: 1243.76.

[0046] Example 11: Synthesis of Compound 22 Compound 22 was prepared according to the preparation scheme of Example 1. The yield of the final product was 21%. Mass spectrometry m / z: theoretical value 1124.71; measured value M+H: 1125.75.

[0047] Example 12: Synthesis of Compound 23 Compound 23 was prepared according to the preparation scheme of Example 1. The yield of the final product was 25%. Mass spectrometry m / z: theoretical value 1150.82; measured value M+H: 1151.87.

[0048] Example 13: Synthesis of Compound 24 Compound 24 was prepared according to the preparation scheme of Example 1. The yield of the final product was 27%. Mass spectrometry m / z: theoretical value 1120.77; measured value M+H: 1121.81.

[0049] Example 14: Synthesis of Compound 27 Compound 27 was prepared according to the preparation scheme of Example 1. The yield of the final product was 24%. Mass spectrometry m / z: theoretical value 1230.70; measured value M+H: 1231.76.

[0050] Example 15: Synthesis of Compound 28 Compound 28 was prepared according to the preparation scheme of Example 1. The yield of the final product was 23%. Mass spectrometry m / z: theoretical value 1128.56; measured value M+H: 1129.59.

[0051] Example 16: Synthesis of Compound 30 Compound 30 was prepared according to the preparation scheme of Example 1. The yield of the final product was 24%. Mass spectrometry m / z: theoretical value 1190.67; measured value M+H: 1191.71.

[0052] Example 17: Synthesis of Compound 31 Compound 31 was prepared according to the preparation scheme of Example 1. The yield of the final product was 25%. Mass spectrometry m / z: theoretical value 1168.64; measured value M+H: 1169.67.

[0053] Example 18: Synthesis of Compound 36 Compound 36 was prepared according to the preparation scheme of Example 1. The yield of the final product was 26%. Mass spectrometry m / z: theoretical value 1298.85; measured value M+H: 1299.88.

[0054] Example 19: Synthesis of Compound 37 Compound 37 was prepared according to the preparation scheme of Example 1. The yield of the final product was 23%. Mass spectrometry m / z: theoretical value 1202.67; measured value M+H: 1203.69.

[0055] Example 20: Synthesis of Compound 41 Compound 41 was prepared according to the preparation scheme of Example 1. The yield of the final product was 31%. Mass spectrometry m / z: theoretical value 1210.73; measured value M+H: 1211.77.

[0056] Example 21: Synthesis of Compound 42 Compound 42 was prepared according to the preparation scheme of Example 1. The yield of the final product was 24%. Mass spectrometry m / z: theoretical value 1243.69; measured value M+H: 1244.73.

[0057] Example 22: Synthesis of Compound 47 Compound 47 was prepared according to the preparation scheme of Example 1. The yield of the final product was 27%. Mass spectrometry m / z: theoretical value 1210.73; measured value M+H: 1211.75.

[0058] Example 23: Synthesis of Compound 57 Compound 57 was prepared according to the preparation scheme of Example 1. The yield of the final product was 22%. Mass spectrometry m / z: theoretical value 1299.75; measured value M+H: 1300.79.

[0059] Example 24: Synthesis of Compound 59 Compound 59 was prepared according to the preparation scheme of Example 1. The yield of the final product was 22%. Mass spectrometry m / z: theoretical value 1206.70; measured value M+H: 1207.77.

[0060] Example 25: Synthesis of Compound 73 Compound 73 was prepared according to the preparation scheme of Example 1. The yield of the final product was 24%. Mass spectrometry m / z: theoretical value 1234.64; measured value M+H: 1235.68.

[0061] Example 26: Synthesis of Compound 80 Compound 80 was prepared according to the preparation scheme of Example 1. The yield of the final product was 23%. Mass spectrometry m / z: theoretical value 1128.65; measured value M+H: 1129.68.

[0062] Example 27: Synthesis of Compound 84 Compound 84 was prepared according to the preparation scheme of Example 1. The yield of the final product was 26%. Mass spectrometry m / z: theoretical value 1138.63; measured value M+H: 1139.67.

[0063] Example 28: Synthesis of Compound 85 Compound 85 was prepared according to the preparation scheme of Example 1. The yield of the final product was 23%. Mass spectrometry m / z: theoretical value 1260.85; measured value M+H: 1261.89.

[0064] Example 29: Synthesis of Compound 88 Compound 88 was prepared according to the preparation scheme of Example 1. The yield of the final product was 22%. Mass spectrometry m / z: theoretical value 1198.63; measured value M+H: 1199.65.

[0065] Example 30: Synthesis of Compound 97 Compound 97 was prepared according to the preparation scheme of Example 1. The yield of the final product was 23%. Mass spectrometry m / z: theoretical value 1360.85; measured value M+H: 1361.89.

[0066] Example 31: Synthesis of Compound 104 Compound 104 was prepared according to the preparation scheme of Example 1. The yield of the final product was 21%. Mass spectrometry m / z: theoretical value 1240.68; measured value M+H: 1241.74.

[0067] Example 32: Synthesis of Compound 115 Compound 115 was prepared according to the preparation scheme of Example 1. The yield of the final product was 22%. Mass spectrometry m / z: theoretical value 1178.66; measured value M+H: 1179.69.

[0068] Example 33: Synthesis of Compound 117 Compound 117 was prepared according to the preparation scheme of Example 1. The yield of the final product was 24%. Mass spectrometry m / z: theoretical value 1128.65; measured value M+H: 1129.68.

[0069] Example 34: Synthesis of Compound 120 Compound 120 was prepared according to the preparation scheme of Example 1. The yield of the final product was 25%. Mass spectrometry m / z: theoretical value 1128.65; measured value M+H: 1129.69.

[0070] Manufacturing of OLED devices: 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-depositing 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-depositing 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 64:32:3:1. Finally, a 35 nm electron transport layer (ETL) is formed by co-depositing. Then, a cathode Al of 70 nm is deposited to fabricate an organic light-emitting diode.

[0071] In a preferred embodiment, the structure of the bottom-emitting OLED device provided by the present invention is as follows: ITO-containing glass is used as the anode; HIL (HT-17:P-2, mass ratio 97:3) with a thickness of 10 nm is deposited sequentially; HTL (HT-10, mass ratio 60 nm); EBL (HT-5, mass ratio 20 nm); EML (GH-1:GH-2):GD-Ir:boron-nitrogen compound 1 provided by the present invention, mass ratio 64:32:3:1, mass ratio 35 nm); ETL (ET-2:LiQ, mass ratio 50:50, mass ratio 35 nm); EIL is a 1 nm LiF layer; then, a cathode Al layer of 70 nm is deposited to prepare an organic light-emitting diode, referred to as Application Example 1.

[0072] 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 2-32 and Comparative Example 1, 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.

[0073] Table 1. Data on the light emission characteristics of the device

[0074] As shown in Table 1, the compounds of the present invention, when used as light-emitting layer materials in electronic devices, exhibit higher current efficiency and lifetime. Compared with Comparative Example 1, Application Examples 1 to 32 all demonstrate excellent device performance in terms of current efficiency and lifetime. The improvement in device performance is achieved based on the better electron transport capability of the boron nitride compound materials of the present invention. This indicates that the boron nitride compounds provided by the present invention have certain commercial application value.

[0075] 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, ring A is selected from one or more C5-C30 cycloalkyl groups, substituted or unsubstituted with Rn; Rn is independently represented as one or more of hydrogen, deuterium, halogen, cyano, C1-C10 alkyl, C3-C24 cycloalkyl, C2-C10 alkenyl, C2-C10 alkoxy, C6-C10 aryloxy, arylamino, C6-C30 aryl, and C5-C30 heteroaryl; Rn is substituted by a single bond or a fused ring, and Rn can be further substituted by deuterium, C1-C10 alkyl, or C6-C30 aryl. R1 and R2 are each selected from substituted or unsubstituted C3-C24 cycloalkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C5-C30 heteroaryl, whether identical or different. When R1 and R2 contain substitutions, each substitution is independently selected from deuterium, C1-C24 alkyl, C3-C24 cycloalkyl, C6-C30 aryl, or C5-C30 heteroaryl. R3-R6 are monosubstituted or polysubstituted. Each of R3-R6 is independently selected from deuterium, halogen, cyano, or C1-C24 alkyl.

2. The boron-nitrogen compound according to claim 1, characterized in that, R1-R2 are each selected from one or more of the following groups, either identically or differently: phenyl, biphenyl, naphthyl, tetrahydronaphthyl, anthracene, phenanthryl, pyridyl, quinolinyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, and diphenylamino; when substituted, the substitution is monosubstituted, disubstituted, or the maximum number of substitutions, and each substitution is independently selected from deuterium, F, methyl, ethyl, propyl, tert-butyl, phenyltert-butyl, and adamantyl.

3. The boron-nitrogen compound according to claim 1, characterized in that, In Formula I, ring A is selected from the following structures: ， Ra and Rb are monosubstituted or polysubstituted, and each time Ra and Rb are independently selected from one or more of hydrogen, deuterium, methyl, ethyl, propyl, tert-butyl, tert-butyl substituted or unsubstituted phenyl, and tert-butyl substituted or unsubstituted biphenyl.

4. The boron-nitrogen compound according to claim 1, characterized in that, The boron-nitrogen compound is selected from any of the following chemical structures, where "D" represents deuterium: 。 5. The use of the boron nitrogen compound according to any one of claims 1-4 in the preparation of organic electroluminescent devices.

6. 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 1-4.

7. 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 1-4.

8. A composition, characterized in that, The composition comprises a boron nitrogen compound as described in any one of claims 1-4.

9. A formulation, characterized in that, The formulation comprises a boron nitrogen compound as described in any one of claims 1-4 and at least one solvent.

10. A display or lighting device, characterized in that, The device comprises one or more of the organic electroluminescent device of claim 6 and / or the organic optoelectronic device of claim 7.

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