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 large steric hindrance spiro ring group. Specifically, the organic electroluminescent device prepared by using the boron-nitrogen compound as a functional layer, especially as a light-emitting layer, has improved current efficiency, 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] 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. BACKGROUND

[0002] With the development of multimedia technology and the improvement of informationization requirements, the performance requirements of panel displays are getting higher and higher. Among them, OLED has a series of advantages such as self-luminous, low-voltage direct current driving, full solidification, wide viewing angle, rich color, etc., and has attracted widespread attention in the potential application of the new generation of display and lighting technology, and has a very broad application prospect. The organic electroluminescent device is a self-luminous device, and the mechanism of OLED light emission is that under the action of an applied electric field, electrons and holes are injected from the positive and negative poles, respectively, migrate, recombine and decay in the organic material to produce light. The typical structure of OLED includes one or more functional layers of cathode layer, anode layer, electron injection layer, electron transport layer, hole blocking layer, hole transport layer, hole injection layer and light emitting layer. Although the research of organic electroluminescence has developed very rapidly, there are still many problems to be solved, for example, high-efficiency long-life narrow-emission green light material has been a problem to be solved by those skilled in the art. SUMMARY

[0003] The purpose of the present application is to provide a boron-nitrogen compound and an organic electroluminescent device containing the same to solve the problems of the prior art. By introducing a spiro ring steric group, the present application effectively suppresses the interaction between light-emitting molecules. At the same time, by introducing a rigid spiro ring structure to optimize the electron and hole receiving capacity of the boron-nitrogen compound, the energy transfer performance between the host and the guest can be improved, and the concentration of high-energy excitons in the light-emitting layer can be reduced, thereby realizing high-efficiency long-life narrow-emission green light material.

[0004] In order to achieve the purpose of the present application, the technical scheme of the present application is as follows:

[0005] According to one or more embodiments, the present application provides a boron-nitrogen compound, which has a general structure shown in the following formula I;

[0006] ;

[0007] In formula I, ring A, ring B, ring C, ring D are the same or different at each occurrence and are selected from a 5-membered unsaturated carbon ring, an aromatic ring having 6-30 carbon atoms, or a heteroaromatic ring having 3-30 carbon atoms, or a combination thereof;

[0008] R1-R8 are monosubstituted or polysubstituted; each of R1-R8 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.

[0009] X1 and X2 are each independently selected from single bonds and CR a R b BR c ,O,S or Se,R a R b R c Each is independently selected from C1-C24 alkyl, substituted or unsubstituted C6-C30 aryl;

[0010] When R1-R8, X1, X2, R a R b R c When a substitution is present, the substitution may be monosubstituted or polysubstituted, and the substitution may be selected from one or more of deuterium, halogen, C1-C12 alkyl, and C6-C18 aryl; adjacent substituents may be selectively linked to form a ring.

[0011] More preferably, R1 and R2 are each 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.

[0012] R3 and R4 are each independently selected from one or more of hydrogen, deuterium, halogen, C1-C12 alkyl; substituted or unsubstituted C3-C24 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, phenoxy, and phenylthio.

[0013] Preferably, rings A through D are each independently selected from benzene rings, naphthyl rings, anthracene rings, phenanthrene rings, furan rings, thiophene rings, pyrrole rings, oxazole rings, thiazole rings, carbazole rings, pyridine rings, pyrimidine rings, pyrazine rings, triazine rings, quinoline rings, isoquinoline rings, quinazoline rings, benzofuran rings, benzothiophene rings, indole rings, dibenzofuran rings, dibenzothiophene rings, carbazole rings, fluorene rings, benzoquinoline rings, benzoisoquinoline rings, N-phenylcarbazole rings, and combinations thereof.

[0014] Preferably, ring A, ring B, ring C, and ring D are each independently selected from the benzene ring;

[0015] Preferably, one of rings A, B, C, and D is selected from a naphthalene ring, and the others are selected from a benzene ring;

[0016] Preferably, either ring A or ring B is selected from a naphthalene ring, either ring C or ring D is selected from a naphthalene ring, and the others are selected from a benzene ring;

[0017] Preferably, either ring A or ring B is selected from benzothiophene ring or benzofuran ring, and the others are selected from benzene ring;

[0018] Preferably, the boron-nitrogen compound has the following general formula structure:

[0019] ;

[0020] In equations I-1 to I-3, the substitution of R1-R8, ring A, ring B, ring C, and ring D is as defined in equation I; R9-R 11 It can be monosubstituted or polysubstituted; the R9-R 11 Each is independently selected from one or more of hydrogen, deuterium, halogen, C1-C24 alkyl, substituted or unsubstituted C6-C30 aryl; R1 and R2 can be selectively linked into a ring, R9-R 11 Each can be optionally connected to its adjacent R1 and R2 to form a ring.

[0021] Preferably, in formulas I-1 to I-3, R9-R 11 Each is independently selected from one or more of hydrogen, deuterium, F, C1-C12 alkyl, substituted or unsubstituted C6-C18 aryl;

[0022] More preferably, in formulas I-1 to I-3, R9-R 11 Each is independently selected from one or more of hydrogen, deuterium, F, methyl, ethyl, isopropyl, tert-butyl, phenyl, tert-butylphenyl, and naphthyl.

[0023] Preferably, R1-R8 are monosubstituted, disubstituted, or maximally substituted, and each of R1-R8 is independently selected from one or more of hydrogen, deuterium, F, methyl, ethyl, propyl, tert-butyl, pentyl, cyclohexyl, cyclopentyl, adamantyl, phenyl, methylphenyl, tert-butylphenyl, diphenyl, tert-phenyl, naphthyl, anthracene, phenanthrene, pyridyl, quinolinyl, phenoxy, phenylthio, furanyl, thiophene, benzofuranyl, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, tert-butyl-substituted carbazoyl, 9,9-dimethylfluorenyl, and diphenylamino.

[0024] Preferably, the substituent may be further replaced by deuterium or F.

[0025] 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:

[0026] .

[0027] 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.

[0028] 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).

[0029] 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%.

[0030] 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.

[0031] The present invention also provides a composition comprising a boron nitrogen compound having the general structure shown in Formula I above.

[0032] 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.

[0033] 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.

[0034] Compared with the prior art, the beneficial effects of the present invention are:

[0035] This invention provides a boron nitride compound with excellent electron and hole accepting capabilities. By introducing a sterically hindered 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 improving 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

[0036] 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.

[0037] 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.

[0038] 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.

[0039] The term "aryl" or "aromatic ring" 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 6-12 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.

[0040] The term "heteroaryl" or "heteroary ring" as used in this invention refers to a group obtained by replacing one or more aromatic carbon atoms in a 3-30 carbon aryl group with 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 can be a monocyclic heteroaryl or a fused-ring heteroaryl. Examples include pyridyl, pyrrole, pyridinyl, thiophene, furanyl, indolyl, quinolinyl, isoquinolinyl, quinoxalinyl, benzothiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazole, etc., but are not limited thereto.

[0041] In this invention, adjacent substituents can be selectively linked to form a ring. "Ring" refers to a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle. A condensed ring refers to a condensed aliphatic ring, a condensed aromatic ring, a condensed aliphatic heterocycle, a condensed aromatic heterocycle, or a combination thereof.

[0042] 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.

[0043] 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.

[0044] Unless otherwise stated, all commercial reagents used in the following tests should be used directly after purchase.

[0045] 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):

[0046] .

[0047] 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:

[0048] .

[0049] 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:

[0050] .

[0051] 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:

[0052] .

[0053] Example 1: Synthesis of Compound 1

[0054] ;

[0055] Synthesis of compounds 1-3: Compounds 1-1 (1 mmol) and 1-2 (1 mmol) were dissolved in 100 mL of toluene. Sodium tert-butoxide (192 mg, 2 mmol), palladium acetate (0.05 mmol), and tri-tert-butylphosphine tetrafluoroborate (0.5 mmol) were added under a nitrogen atmosphere. The reaction mixture was heated to reflux for 48 hours 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 to give product 1-3 (390 mg, yield 31%). Mass spectrometry m / z: theoretical value 1256.67; measured value M+H: 1257.72.

[0056] 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 solution of compounds 1-3 (1 mmol) in tert-butylbenzene (100 mL). The system was reacted at 60°C for 4 hours, then cooled to -50°C, and BBr3 (2 mmol) was added. After reacting at room temperature for 1 hour, N,N-diisopropylethylamine (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 product 1 (271 mg, yield 22%). Mass spectrometry m / z, theoretical value 1230.70; measured value M+H: 1231.73.

[0057] Example 2: Synthesis of Compound 3

[0058] Compound 3 was prepared according to the preparation scheme of Example 1. The yield of the final product was 23%. Mass spectrometry m / z: theoretical value 1342.82; measured value M+H: 1343.86.

[0059] Example 3: Synthesis of Compound 5

[0060] Compound 5 was prepared according to the preparation scheme of Example 1. The yield of the final product was 27%. Mass spectrometry m / z: theoretical value 1306.73; measured value M+H: 1307.75.

[0061] Example 4: Synthesis of Compound 7

[0062] Compound 7 was prepared according to the preparation scheme of Example 1. The yield of the final product was 26%. Mass spectrometry m / z: theoretical value 1310.67; measured value M+H: 1311.73.

[0063] Example 5; Synthesis of Compound 9

[0064] Compound 9 was prepared according to the preparation scheme of Example 1. The yield of the final product was 25%. Mass spectrometry m / z: theoretical value 1310.67; measured value M+H: 1311.72.

[0065] Example 6: Synthesis of Compound 11

[0066] Compound 11 was prepared according to the preparation scheme of Example 1. The yield of the final product was 21%. Mass spectrometry m / z: theoretical value 1284.61; measured value M+H: 1285.65.

[0067] Example 7: Synthesis of Compound 15

[0068] Compound 15 was prepared according to the preparation scheme of Example 1. The yield of the final product was 21%. Mass spectrometry m / z: theoretical value 1300.59; measured value M+H: 1301.64.

[0069] Example 8: Synthesis of Compound 20

[0070] Compound 20 was prepared according to the preparation scheme of Example 1. The yield of the final product was 23%. Mass spectrometry m / z: theoretical value 1326.70; measured value M+H: 1327.72.

[0071] Example 9: Synthesis of Compound 23

[0072] Compound 23 was prepared according to the preparation scheme of Example 1. The yield of the final product was 21%. Mass spectrometry m / z: theoretical value 1382.76; measured value M+H: 1383.81.

[0073] Example 10: Synthesis of Compound 26

[0074] Compound 26 was prepared according to the preparation scheme of Example 1. The yield of the final product was 22%. Mass spectrometry m / z: theoretical value 1283.63; measured value M+H: 1284.66.

[0075] Example 11: Synthesis of Compound 32

[0076] Compound 32 was prepared according to the preparation scheme of Example 1. The yield of the final product was 24%. Mass spectrometry m / z: theoretical value 1358.67; measured value M+H: 1359.70.

[0077] Example 12: Synthesis of Compound 36

[0078] Compound 36 was prepared according to the preparation scheme of Example 1. The yield of the final product was 22%. Mass spectrometry m / z: theoretical value 1358.67; measured value M+H: 1359.69.

[0079] Example 13: Synthesis of Compound 39

[0080] Compound 39 was prepared according to the preparation scheme of Example 1. The yield of the final product was 25%. Mass spectrometry m / z: theoretical value 1230.70; measured value M+H: 1231.73.

[0081] Example 14: Synthesis of Compound 53

[0082] Compound 53 was prepared according to the preparation scheme of Example 1. The yield of the final product was 23%. Mass spectrometry m / z: theoretical value 1214.57; measured value M+H: 1215.62.

[0083] Example 15: Synthesis of Compound 59

[0084] Compound 59 was prepared according to the preparation scheme of Example 1. The yield of the final product was 24%. Mass spectrometry m / z: theoretical value 1270.63; measured value M+H: 1271.67.

[0085] Example 16: Synthesis of Compound 63

[0086] Compound 63 was prepared according to the preparation scheme of Example 1. The yield of the final product was 24%. Mass spectrometry m / z: theoretical value 1158.51; measured value M+H: 1159.55.

[0087] Example 17: Synthesis of Compound 68

[0088] Compound 68 was prepared according to the preparation scheme of Example 1. The yield of the final product was 21%. Mass spectrometry m / z: theoretical value 1358.67; measured value M+H: 1359.71.

[0089] Example 18: Synthesis of Compound 72

[0090] Compound 72 was prepared according to the preparation scheme of Example 1. The yield of the final product was 26%. Mass spectrometry m / z: theoretical value 1270.63; measured value M+H: 1271.66.

[0091] Example 19: Synthesis of Compound 74

[0092] Compound 74 was prepared according to the preparation scheme of Example 1. The yield of the final product was 26%. Mass spectrometry m / z: theoretical value 1306.73; measured value M+H: 1307.75.

[0093] Example 20: Synthesis of Compound 82

[0094] Compound 82 was prepared according to the preparation scheme of Example 1. The yield of the final product was 21%. Mass spectrometry m / z: theoretical value 1284.61; measured value M+H: 1285.64.

[0095] Example 21: Synthesis of Compound 90

[0096] Compound 90 was prepared according to the preparation scheme of Example 1. The yield of the final product was 22%. Mass spectrometry m / z: theoretical value 1326.70; measured value M+H: 1327.74.

[0097] Example 22: Synthesis of Compound 99

[0098] Compound 199 was prepared according to the preparation scheme of Example 1. The yield of the final product was 23%. Mass spectrometry m / z: theoretical value 1280.70; measured value M+H: 1281.74.

[0099] Example 23: Synthesis of Compound 100

[0100] Compound 100 was prepared according to the preparation scheme of Example 1. The yield of the final product was 25%. Mass spectrometry m / z: theoretical value 1168.59; measured value M+H: 1169.63.

[0101] Example 24: Synthesis of Compound 101

[0102] Compound 101 was prepared according to the preparation scheme of Example 1. The yield of the final product was 22%. Mass spectrometry m / z: theoretical value 1250.67; measured value M+H: 1251.73.

[0103] Example 25: Synthesis of Compound 103

[0104] Compound 103 was prepared according to the preparation scheme of Example 1. The yield of the final product was 23%. Mass spectrometry m / z: theoretical value 1168.59; measured value M+H: 1169.63.

[0105] Example 26: Synthesis of Compound 104

[0106] Compound 104 was prepared according to the preparation scheme of Example 1. The yield of the final product was 26%. Mass spectrometry m / z: theoretical value 1218.60; measured value M+H: 1219.65.

[0107] Example 27: Synthesis of Compound 106

[0108] Compound 106 was prepared according to the preparation scheme of Example 1. The yield of the final product was 24%. Mass spectrometry m / z: theoretical value 1362.79; measured value M+H: 1363.81.

[0109] Example 28: Synthesis of Compound 107

[0110] Compound 107 was prepared according to the preparation scheme of Example 1. The yield of the final product was 22%. Mass spectrometry m / z: theoretical value 1280.71; measured value M+H: 1281.74.

[0111] Example 29: Synthesis of Compound 110

[0112] Compound 110 was prepared according to the preparation scheme of Example 1. The yield of the final product was 21%. Mass spectrometry m / z: theoretical value 1374.81; measured value M+H: 1375.85.

[0113] Example 30: Synthesis of Compound 111

[0114] Compound 111 was prepared according to the preparation scheme of Example 1. The yield of the final product was 26%. Mass spectrometry m / z: theoretical value 1342.75; measured value M+H: 1343.78.

[0115] Example 31: Synthesis of Compound 115

[0116] Compound 115 was prepared according to the preparation scheme of Example 1. The yield of the final product was 23%. Mass spectrometry m / z: theoretical value 1318.75; measured value M+H: 1319.79.

[0117] Example 32: Synthesis of Compound 116

[0118] Compound 116 was prepared according to the preparation scheme of Example 1. The yield of the final product was 29%. Mass spectrometry m / z: theoretical value 1368.70; measured value M+H: 1369.74.

[0119] Example 33: Synthesis of Compound 119

[0120] Compound 119 was prepared according to the preparation scheme of Example 1. The yield of the final product was 22%. Mass spectrometry m / z: theoretical value 1306.73; measured value M+H: 1307.78.

[0121] Example 34: Synthesis of Compound 121

[0122] Compound 121 was prepared according to the preparation scheme of Example 1. The yield of the final product was 21%. Mass spectrometry m / z: theoretical value 1300.68; measured value M+H: 1301.74.

[0123] Example 35: Synthesis of Compound 123

[0124] Compound 123 was prepared according to the preparation scheme of Example 1. The yield of the final product was 24%. Mass spectrometry m / z: theoretical value 1254.70; measured value M+H: 1255.74.

[0125] Example 36: Synthesis of Compound 128

[0126] Compound 128 was prepared according to the preparation scheme of Example 1. The yield of the final product was 22%. Mass spectrometry m / z: theoretical value 1356.74; measured value M+H: 1357.77.

[0127] Example 37: Synthesis of Compound 129

[0128] Compound 129 was prepared according to the preparation scheme of Example 1. The yield of the final product was 21%. Mass spectrometry m / z: theoretical value 1350.70; measured value M+H: 1351.74.

[0129] Example 38: Synthesis of Compound 131

[0130] Compound 131 was prepared according to the preparation scheme of Example 1. The yield of the final product was 23%. Mass spectrometry m / z: theoretical value 1356.74; measured value M+H: 1357.76.

[0131] Example 39: Synthesis of Compound 133

[0132] Compound 133 was prepared according to the preparation scheme of Example 1. The yield of the final product was 27%. Mass spectrometry m / z: theoretical value 1270.69; measured value M+H: 1271.72.

[0133] Example 40: Synthesis of Compound 135

[0134] Compound 135 was prepared according to the preparation scheme of Example 1. The yield of the final product was 25%. Mass spectrometry m / z: theoretical value 1290.70; measured value M+H: 1291.73.

[0135] Example 41: Synthesis of Compound 136

[0136] Compound 136 was prepared according to the preparation scheme of Example 1. The yield of the final product was 22%. Mass spectrometry m / z: theoretical value 1224.65; measured value M+H: 1225.69.

[0137] Example 42: Synthesis of Compound 138

[0138] Compound 138 was prepared according to the preparation scheme of Example 1. The yield of the final product was 26%. Mass spectrometry m / z: theoretical value 1342.82; measured value M+H: 1343.85.

[0139] Manufacturing of OLED devices:

[0140] 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 65:31:3:1. Finally, an electron transport layer (ETL) of 30-50 nm is formed by co-evaporating the host material. Then, a cathode of Al 70 nm is deposited to fabricate an organic light-emitting diode.

[0141] 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 HT-1:P-3 (mass ratio 97:3) with a thickness of 10 nm; HTL is HT-3 with a thickness of 60 nm; EBL is HT-14 with a thickness of 20 nm; EML is the host material (GH-1:GH-2):GD-Ir: the boron nitrogen compound 1 provided by the present invention (mass ratio 65:31:3:1) with a thickness of 40 nm; ETL is ET-6:LiQ (mass ratio 50:50) with a thickness of 40 nm; EIL is a 1 nm LiF layer; then the cathode Al is deposited with a thickness of 70 nm to prepare an organic light-emitting diode, referred to as Application Example 1.

[0142] 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 38 and Comparative Examples 1-2, respectively. The compound structures in the comparative examples are shown below:

[0143]

[0144] The current efficiency and lifetime of the devices prepared above were tested using standard methods in application examples and comparative examples. The device luminescence characteristics data are shown in Table 1.

[0145] Table 1. Data on the light emission characteristics of the device

[0146]

[0147] 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 1-2, Application Examples 1 to 38 demonstrate superior device performance in both current efficiency and lifetime. The performance improvements in each device are achieved based on the better electron transport capabilities of the boron nitride compound materials of this invention. This indicates that the boron nitride compounds provided by this invention have certain commercial application value.

[0148] 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-1: ； In Formula I-1, rings A, B, C, and D are selected from benzene rings; R1-R8 are monosubstituted or polysubstituted; each of R1-R2 is independently selected from one or more of hydrogen, deuterium, C1-C24 alkyl, C3-C24 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and C5-C30 heteroaryl; the heteroatom is selected from O, S, and N; each of R3-R4 is independently selected from C1-C24 alkyl; each of R5-R8 is independently selected from one or more of hydrogen, deuterium, C1-C24 alkyl, and substituted or unsubstituted C6-C30 aryl; when R1-R8 contains a substituted substance, the substituted substance is optionally selected from one or more of deuterium and C1-C12 alkyl.

2. The boron-nitrogen compound according to claim 1, characterized in that, R1 and R2 are monosubstituted, disubstituted, or maximally substituted, and each of R1-R2 is independently selected from one or more of hydrogen, deuterium, methyl, ethyl, propyl, tert-butyl, cyclopentyl, phenyl, methylphenyl, tert-butylphenyl, diphenyl, naphthyl, phenanthryl, dibenzofuranyl, dibenzothiophene, carbazolyl, and 9,9-dimethylfluorenyl.

3. The boron-nitrogen compound according to claim 1, characterized in that, R3 and R4 are each independently selected from hydrogen, deuterium, methyl, ethyl, propyl, and tert-butyl.

4. The boron-nitrogen compound according to claim 1, characterized in that, R5-R8 are monosubstituted, disubstituted, or maximally substituted, and each of R5-R8 is independently selected from one or more of hydrogen, deuterium, methyl, ethyl, propyl, tert-butyl, phenyl, tert-butylphenyl, and naphthyl.

5. A boron-nitrogen compound, characterized in that, The boron-nitrogen compound is selected from any of the chemical structures shown below, where "D" represents deuterium: 。 6. The application of the boron-nitrogen compound according to any one of claims 1-5 in the preparation of electronic devices, wherein the electronic device is an organic electroluminescent device.

7. 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 1-5.

8. 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 1-5.

9. A composition, characterized in that, The composition comprises a boron nitrogen compound as described in any one of claims 1-5.

10. A formulation, characterized in that, The formulation comprises a boron nitrogen compound as described in any one of claims 1-5 and at least one solvent.

11. A display or lighting device, characterized in that, The device comprises one or more of the organic electroluminescent device of claim 7 and / or the organic optoelectronic device of claim 8.

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