Boron nitrogen compounds containing imidazole and derivative groups, organic electroluminescent devices and applications

Abstract

The present invention relates to the technical field of organic photoelectric material preparation, and specifically to boron nitrogen compounds containing imidazole and derivative groups, organic electroluminescent devices and applications. The boron nitrogen compounds provided by the present invention have a good ability to balance carrier transmission, and can improve the energy transmission performance and exciton utilization efficiency between the host and the guest; when used as a functional layer, especially as a light-emitting layer in an organic electroluminescent device, the current efficiency is improved, and the life of the device is also greatly improved.

Description

Technical Field

[0001] The invention relates to the technical field of organic photoelectric material preparation, and in particular to boron nitrogen compounds containing imidazole and derivative groups, organic electroluminescent devices and applications. Background Art

[0002] With the development of multimedia technology and the improvement of information requirements, the requirements for panel display performance are getting higher and higher. Among them, OLED has a series of advantages such as autonomous luminescence, low-voltage DC drive, full curing, wide viewing angle, rich colors, etc., and has attracted widespread attention for its potential application in the new generation of display and lighting technology, and its application prospects are very broad. Organic electroluminescent devices are spontaneous luminescent devices. The luminescence mechanism of OLED is that under the action of an external electric field, electrons and holes are injected from the positive and negative electrodes respectively, and then migrate, recombine and decay in the organic material to produce luminescence. 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 luminescent layer. Although the research on organic electroluminescence has progressed very rapidly, new luminescent materials are still in urgent need of development, especially the development and design of high-efficiency and long-life luminescent host materials. Summary of the invention

[0003] The purpose of the present invention is to provide a boron nitrogen compound containing imidazole and derivative groups, an organic electroluminescent device and applications thereof in view of the deficiencies in the prior art. The boron nitrogen compound of the present invention improves the thermal stability of the compound and its carrier transport capacity by introducing imidazole and imidazole derivative groups, and can effectively improve the energy transfer performance between the host and the guest after the device is prepared.

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

[0005] According to one or more embodiments, the present invention provides a boron nitrogen compound, wherein the boron nitrogen compound contains imidazole and a derivative group, and has a structure shown in the following formula (I):

[0006] ;

[0007] In formula (I), X1-X 10 Each is independently selected from CR or N; said R is independently selected from hydrogen, deuterium, C1-C24 alkyl, C3-C24 cycloalkyl, substituted or unsubstituted C3-C24 arylsilyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;

[0008] The R1-R3 are each independently selected from hydrogen, deuterium, C1-C24 alkyl, C3-C24 cycloalkyl, substituted or unsubstituted C3-C24 alkylsilyl, substituted or unsubstituted C3-C24 arylsilyl, substituted or unsubstituted C1-C30 arylamine, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;

[0009] The R4 and R5 are each independently selected from hydrogen, deuterium, C1-C24 alkyl, C3-C24 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; R, R1-R5 represent a polysubstituted group, which may be unsubstituted, monosubstituted or polysubstituted; in the case of being substituted by multiple substituents, the multiple substituents are the same or different from each other; when R, R1-R5 contain substitutions, the substituents are selected from any one or more of hydrogen, deuterium, C1-C24 alkyl, C6-C30 aryl, C3-C30 heteroaryl; when containing heteroatoms, the heteroatoms are selected from N, O, S.

[0010] In many embodiments, R1 is selected from C1~C3 alkyl, R2 is selected from deuterium, C1~C5 alkyl, triarylsilyl, substituted or unsubstituted C6~C18 aryl, substituted or unsubstituted C3~C18 heteroaryl, substituted or unsubstituted C6~C18 arylaminealkyl, substituted or unsubstituted C6~C18 heteroarylaminealkyl; the substituent is selected from hydrogen, deuterium, C1~C12 alkyl, C6~C18 aryl, C3~C18 nitrogen heteroaryl.

[0011] Preferably, R1 is selected from tert-butyl; R2 is selected from tert-butyl, phenyl, biphenyl, tert-butyl substituted biphenyl, phenylpyridyl, triphenylsilyl, substituted or unsubstituted dibenzofuranyl, tert-butyl substituted dibenzofuranyl, dibenzothienyl, substituted or unsubstituted diphenylamine, substituted or unsubstituted pyridylphenylamine, the substitution may be mono- or poly-substituted, and the substituent is selected from hydrogen, deuterium, tert-butyl, phenyl, pyridyl.

[0012] In many embodiments, the R3 is selected from substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl; the substituent is selected from deuterium, tert-butyl, carbazolyl.

[0013] Preferably, R3 is selected from hydrogen, deuterium, methyl, ethyl, propyl, tert-butyl, phenyl, tert-butylphenyl, pyridyl, dibenzofuranyl, and dibenzothiophenyl.

[0014] In many embodiments, R is independently selected from one or more of hydrogen, deuterium, methyl, ethyl, propyl, tert-butyl, pyridyl, adamantyl, phenyl, tert-butylphenyl, dibenzofuranyl, dibenzothienyl, and triphenylsilyl.

[0015] In many embodiments, R4 and R5 are each independently selected from hydrogen, deuterium, tert-butyl, phenyl, pyridyl, methyl-substituted tetrahydronaphthyl; R4 and R5 can be connected by chemical bonds to form a ring structure, preferably, the ring structure is phenyl, pyridyl, cyclopentyl.

[0016] At least one hydrogen in the compound represented by formula (I) of the present invention may be substituted by deuterium, tritium, cyano or halogen.

[0017] According to one or more embodiments, the boron nitrogen compound is selected from any one of the chemical structures shown below, wherein "D" represents deuterium:

[0018]

[0019] According to one or more embodiments, the present invention also provides use of a boron nitrogen compound having a general structure as shown in formula (I) above in the preparation of an electronic device.

[0020] In a preferred embodiment, the electronic devices include organic electroluminescent devices (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 optical detectors, organic photoreceptors, organic field quenching devices (O-FQDs), light emitting electrochemical cells (LECs), and organic laser diodes (O-lasers).

[0021] According to one or more embodiments, the present invention further provides an organic electroluminescent device, which includes a boron nitrogen compound having a general structure as shown in the above formula (I).

[0022] In a preferred embodiment, the organic electroluminescent device comprises a cathode, an anode and an organic functional layer therebetween; the organic functional layer comprises a light-emitting layer, and the light-emitting layer comprises a boron-nitrogen compound having a general structure as shown in formula (I) above, wherein the mass percentage of the boron-nitrogen compound is between 0.1% and 50%.

[0023] According to one or more embodiments, the present invention also provides an organic photoelectric device, comprising a substrate layer; 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 nitrogen compound having a general structure as shown in formula (I) above. For example, the boron nitrogen compound can be included in the light-emitting material layer as a guest material.

[0024] The present invention also provides a composition, which comprises a boron-nitrogen compound having a general structure as shown in the above formula (I).

[0025] The present invention also provides a preparation, which comprises a boron nitrogen compound having a general structure as shown in the above formula (I) or a composition as described above, and at least one solvent. The solvent is not particularly limited, and can be used as those 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, tetralin, n-butylbenzene, sec-butylbenzene or tert-butylbenzene; the halogenated saturated hydrocarbon solvent is carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, hexyl chloride, bromohexane, chlorocyclohexane or bromocyclohexane; the halogenated unsaturated hydrocarbon solvent is chlorobenzene, dichlorobenzene or trichlorobenzene; the ether solvent is tetrahydrofuran or tetrahydropyran; the ester solvent is an alkyl benzoate.

[0026] The present invention also provides a display or lighting device, which comprises one or more of the organic electroluminescent devices described above.

[0027] Compared with the prior art, the present invention has the following beneficial effects:

[0028] The boron nitrogen compounds involved in the present invention have good thermal stability and good balanced carrier transmission ability, which can improve the energy transmission performance and exciton utilization efficiency between the host and the guest; specifically, the boron nitrogen compounds of the present invention are used as functional layers, especially as light-emitting layers to make organic electroluminescent devices, so that the current efficiency is improved, and the life of the device is also greatly improved, indicating that after most electrons and holes recombine, the energy is effectively transferred to the boron nitrogen compounds of the present invention for luminescence rather than heat generation. DETAILED DESCRIPTION

[0029] The content of the present invention is described in detail below. The description of the constituent elements recorded below is sometimes based on representative embodiments or specific examples of the present invention, but the present invention is not limited to such embodiments or specific examples. By referring to the following specific embodiments and the examples contained therein, the present disclosure can be more easily understood. 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, because this can be varied. It should also be understood that the terms used in the present invention are only used to describe specific aspects and are not intended to be limiting. Although any methods and materials similar or equivalent to those described in the present invention can be used in the practice or test, exemplary methods and materials are now described.

[0030] The term "alkyl" as used herein refers to a monovalent alkyl group having 1 to 24 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms. Examples of this term include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-hexyl, etc.

[0031] The present invention's "cycloalkyl" refers to a cyclic alkyl group having 3 to 24 carbon atoms and having a monocyclic or polycyclic condensed group, which can be arbitrarily substituted by 1 to 3 alkyl groups. Such cycloalkyl groups include, for example, monocyclic structures such as cyclopropyl, cyclobutyl, cyclopentyl, cyclooctyl, 1-methylcyclopropyl, and 2-methylcyclopentyl, 2-methylcyclooctyl, etc., or polycyclic structures such as adamantyl, etc.

[0032] The "aryl" of the present invention refers to an unsaturated aromatic carbocyclic ring having 6-30 carbon atoms and having a monocyclic (such as phenyl) or polycyclic condensation (such as naphthyl or anthracenyl), preferably having 6-18 carbon atoms, more preferably 1-12 carbon atoms. Preferred aryl groups include phenyl, naphthyl, etc. Unless otherwise defined for individual substituents, such aryl groups may be optionally substituted by 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, heterocycle, thioalkoxy, trihalomethyl, etc. Preferred substituents include alkyl, alkoxy, halogen, cyano, nitro, trihalomethyl and thioalkoxy. But not limited thereto.

[0033] The "heteroaryl" mentioned in the present invention refers to a general term for groups in which one or more aromatic carbon atoms in an aromatic group are replaced by heteroatoms, wherein the heteroatoms include but are not limited to oxygen, sulfur or nitrogen atoms. The heteroaryl group may be a monocyclic heteroaryl group or a condensed-ring heteroaryl group. Examples may include pyridyl, pyrrolyl, pyridyl, thienyl, furyl, indolyl, quinolyl, isoquinolyl, benzothienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, etc., but are not limited thereto.

[0034] As used in the specification, the singular forms "a", "an" and "the" include plural referents unless the context clearly dictates otherwise. Thus, for example, reference to "a component" includes a mixture of two or more components.

[0035] Unless otherwise stated, all commercial reagents involved in the following experiments were used directly after purchase.

[0036] In a preferred embodiment of the present invention, the OLED device of the present invention contains a hole transport layer, and the hole transport material can be preferably selected from known or unknown materials, and is particularly preferably selected from the following structures, but it does not mean that the present invention is limited to the following structures (Ph is phenyl):

[0037]

[0038] In a preferred embodiment of the present invention, the hole injection layer contained in the OLED device of the present invention. The preferred hole injection layer material of the present invention is the following structure, but it does not mean that the present invention is limited to the following structure:

[0039]

[0040] In a preferred embodiment of the present invention, the electron transport layer can be selected from at least one of the following compounds, but it does not mean that the present invention is limited to the following structures:

[0041] .

[0042] The preparation method of the boron nitrogen compound containing imidazole groups, i.e., the guest compound, and the luminescent properties of the device are explained in detail in conjunction with the following examples.

[0043] The OLED device of the present invention contains a host material, which can be selected from known or unknown materials, and is particularly preferably selected from the following structures, but it does not mean that the present invention is limited to the following structures:

[0044]

[0045] Example 1: Synthesis of Compound 1

[0046] (1) Synthesis of Compounds 1-3

[0047] Compound 1-1 (268 mg, 1 mmoL) and compound 1-2 (225 mg, 1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (192 mg, 2 mmoL), palladium acetate (12 mg, 0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (145 mg, 0.5 mmoL) were added. The reaction system was refluxed for 72 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 with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography, with the eluent being dichloromethane: petroleum ether = 1:5, to obtain product 1-3 (213 mg, yield 52%). Mass spectrum m / z, theoretical value 413.22; measured value M+H: 414.24;

[0048] (2) Synthesis of Compounds 1-5

[0049] Compound 1-3 (413 mg, 1 mmoL) and compound 1-4 (488 mg, 1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (192 mg, 2 mmoL), palladium acetate (12 mg, 0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (145 mg, 0.5 mmoL) were added. The reaction system was refluxed for 72 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 with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography, with the eluent being dichloromethane: petroleum ether = 1:6, to obtain product 1-5 (346 mg, yield 45%). Mass spectrum m / z, theoretical value 770.97; measured value M+H: 771.99;

[0050] (3) Synthesis of Compounds 1-8

[0051] Compound 1-6 (336 mg, 1 mmoL) and compound 1-7 (329 mg, 1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, 10 mL sodium carbonate aqueous solution (2 M) and tetrakis(triphenylphosphine)palladium (57 mg, 0.05 mmoL) were added. The reaction system was refluxed for 72 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 with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography, with the eluent being dichloromethane: petroleum ether = 1:9, to obtain product 1-8 (263 mg, yield 64%). Mass spectrum m / z, theoretical value 412.07; measured value M+H: 413;

[0052] (4) Synthesis of Compounds 1-10

[0053] Compound 1-8 (412 mg, 1 mmoL) and compound 1-9 (169 mg, 1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (192 mg, 2 mmoL), palladium acetate (12 mg, 0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (145 mg, 0.5 mmoL) were added. The reaction system was refluxed for 72 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 with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography, with the eluent being dichloromethane: petroleum ether = 1:5, to obtain product 1-10 (231 mg, yield 51%). Mass spectrum m / z, theoretical value 453.25; measured value M+H: 454.28;

[0054] (5) Synthesis of Compounds 1-11

[0055] Compound 1-5 (771 mg, 1 mmoL) and compound 1-10 (453 mg, 1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (192 mg, 2 mmoL), palladium acetate (12 mg, 0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (145 mg, 0.5 mmoL) were added. The reaction system was refluxed for 72 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 with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography, with the eluent being dichloromethane: petroleum ether = 1:5, to obtain product 1-11 (467 mg, yield 43%). Mass spectrum m / z, theoretical value 1096.30; measured value M+H: 1097.33;

[0056] (6) Synthesis of Compounds 1-12

[0057] Compound 1-11 (1096 mg, 1 mmoL) was dissolved in 60 mL of anhydrous 1,2-dichlorobenzene. The reaction system was cooled to 0°C, and BuLi (0.5 mL, 1 mmoL, 2M in hexane) was slowly added. The reaction system was reacted at room temperature for 4 hours and then cooled to 0°C, and BBr3 (494 mg, 2 mmoL) was slowly added. After reacting at 0°C for 1 hour, the reaction was heated to room temperature, and then N,N-diisopropylethylamine (387 mg, 3 mmoL) was added, followed by heating to 130°C for 24 hours. After cooling to room temperature, 2 mL of N,N-diisopropylethylamine 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 distillation under reduced pressure, and the crude product was separated and purified by silica gel chromatography, with the eluent being dichloromethane: petroleum ether = 1:2, to obtain product 1-12 (286 mg, yield 28%). Mass spectrum m / z, theoretical value 1026.38; measured value M+H: 1027.41;

[0058] (7) Synthesis of compound 1

[0059] Compound 1-12 (1028 mg, 1 mmoL) and compound 1-13 (250 mg, 1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (192 mg, 2 mmoL), palladium acetate (12 mg, 0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (145 mg, 0.5 mmoL) were added. The reaction system was refluxed for 72 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 with sodium sulfate. The solvent was removed by vacuum distillation, and the crude product was separated and purified by silica gel chromatography, with the eluent being dichloromethane: petroleum ether = 1:2, to obtain product 1 (324 mg, yield 27%). Mass spectrum m / z, theoretical value 1196.60; measured value M+H: 1197.62.

[0060] Example 2: Synthesis of Compound 5

[0061] Compound 5 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 28%. Mass spectrum m / z, theoretical value 1194.58; measured value M+H: 1195.61.

[0062] Example 3: Synthesis of Compound 7

[0063] Compound 7 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 21%. Mass spectrum m / z, theoretical value 1231.58; measured value M+H: 1232.60.

[0064] Example 4: Synthesis of Compound 10

[0065] Compound 10 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 24%. Mass spectrum m / z, theoretical value 1252.54; measured value M+H: 1253.56.

[0066] Example 5: Synthesis of Compound 15

[0067] Compound 15 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 21%. Mass spectrum m / z, theoretical value 1246.56; measured value M+H: 1247.58.

[0068] Example 6: Synthesis of Compound 18

[0069] Compound 18 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 25%. Mass spectrum m / z, theoretical value 1210.71; measured value M+H: 1211.74.

[0070] Example 7: Synthesis of Compound 19

[0071] Compound 19 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 26%. Mass spectrum m / z, theoretical value 1309.62; measured value M+H: 1310.64.

[0072] Example 8: Synthesis of Compound 27

[0073] Compound 27 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 31%. Mass spectrum m / z, theoretical value 1175.55; measured value M+H: 1176.57.

[0074] Example 9: Synthesis of Compound 31

[0075] Compound 31 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 25%. Mass spectrum m / z, theoretical value 1241.62; measured value M+H: 1242.64.

[0076] Example 10: Synthesis of Compound 36

[0077] Compound 36 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 29%. Mass spectrum m / z, theoretical value 1194.51; measured value M+H: 1195.53.

[0078] Example 11: Synthesis of Compound 37

[0079] Compound 37 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 31%. Mass spectrum m / z, theoretical value 1139.44; measured value M+H: 1140.46.

[0080] Example 12: Synthesis of Compound 40

[0081] Compound 40 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 27%. Mass spectrum m / z, theoretical value 1154.51; measured value M+H: 1155.53.

[0082] Example 13: Synthesis of Compound 48

[0083] Compound 48 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 25%. Mass spectrum m / z, theoretical value 1244.65; measured value M+H: 1245.67.

[0084] Example 14: Synthesis of Compound 49

[0085] Compound 49 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 24%. Mass spectrum m / z, theoretical value 1172.48; measured value M+H: 1173.51.

[0086] Example 15: Synthesis of Compound 50

[0087] Compound 50 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 21%. Mass spectrum m / z, theoretical value 1150.52; measured value M+H: 1151.54.

[0088] Example 16: Synthesis of Compound 55

[0089] Compound 55 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 27%. Mass spectrum m / z, theoretical value 1284.52; measured value M+H: 1285.55.

[0090] Example 17: Synthesis of Compound 64

[0091] Compound 64 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 28%. Mass spectrum m / z, theoretical value 1204.57; measured value M+H: 1205.59.

[0092] Example 18: Synthesis of Compound 69

[0093] Compound 69 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 25%. Mass spectrum m / z, theoretical value 1226.59; measured value M+H: 1227.62.

[0094] Example 19: Synthesis of Compound 73

[0095] Compound 73 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 28%. Mass spectrum m / z, theoretical value 1305.63; measured value M+H: 1306.65.

[0096] Example 20: Synthesis of Compound 81

[0097] Compound 81 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 32%. Mass spectrum m / z, theoretical value 1251.64; measured value M+H: 1252.66.

[0098] Example 21: Synthesis of Compound 83

[0099] Compound 83 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 27%. Mass spectrum m / z, theoretical value 1232.57; measured value M+H: 1233.59.

[0100] Example 22: Synthesis of Compound 86

[0101] Compound 86 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 24%. Mass spectrum m / z, theoretical value 1236.60; measured value M+H: 1237.62.

[0102] Example 23: Synthesis of Compound 105

[0103] Compound 105 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 23%. Mass spectrum m / z, theoretical value 1281.54; measured value M+H: 1282.57.

[0104] Example 24: Synthesis of Compound 110

[0105] Compound 110 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 28%. Mass spectrum m / z, theoretical value 1281.50; measured value M+H: 1282.52.

[0106] Example 25: Synthesis of Compound 112

[0107] Compound 112 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 31%. Mass spectrum m / z, theoretical value 1210.58; measured value M+H: 1211.59.

[0108] Example 26: Synthesis of Compound 121

[0109] Compound 121 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 24%. Mass spectrum m / z, theoretical value 1288.63; measured value M+H: 1289.65.

[0110] Example 27: Synthesis of Compound 131

[0111] Compound 131 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 26%. Mass spectrum m / z, theoretical value 1333.62; measured value M+H: 1334.65.

[0112] Example 28: Synthesis of Compound 135

[0113] Compound 135 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 27%. Mass spectrum m / z, theoretical value 1354.71; measured value M+H: 1355.73.

[0114] Example 29: Synthesis of Compound 142

[0115] Compound 142 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 23%. Mass spectrum m / z, theoretical value 1202.49; measured value M+H: 1203.52.

[0116] Example 30: Synthesis of Compound 148

[0117] Compound 148 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 26%. Mass spectrum m / z, theoretical value 1243.58; measured value M+H: 1244.61.

[0118] Example 31: Synthesis of Compound 153

[0119] Compound 153 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 25%. Mass spectrum m / z, theoretical value 1259.55; measured value M+H: 1260.57.

[0120] Example 32: Synthesis of Compound 157

[0121] Compound 157 was synthesized by referring to the preparation route of compound 1. The yield of the final product was 21%. Mass spectrum m / z, theoretical value 1293.69; measured value M+H: 1294.72.

[0122] Fabrication of OLED devices:

[0123] As a reference preparation method for a device embodiment, the present invention evaporates a p-doped material on the surface of an ITO glass with a light-emitting area of ​​2 mm×2 mm or on an anode, or co-evaporates the p-doped material with a hole transport material at a concentration of 1% to 50% to form a 5-100 nm hole injection layer (HIL), forms a 5-200 nm hole transport layer (HTL) on the hole injection layer, then co-evaporates a host material and an imidazole compound (guest material) prepared by the present invention on the hole transport layer at a weight ratio of 97:3 to form a 10-100 nm light-emitting layer (EML), and finally co-evaporates to form a 35 nm electron transport layer (ETL), and then evaporates 70 nm of cathode Al, thereby manufacturing an organic electroluminescent diode.

[0124] In a preferred specific embodiment, the structure of the bottom-emitting OLED device provided by the present invention is: glass containing ITO is used as the anode, and HIL is sequentially evaporated to be HT-4:P-3 (weight ratio is 95:5) with a thickness of 10 nanometers; HTL is HT-4 with a thickness of 90 nanometers; EBL is HT-9 with a thickness of 10 nanometers, and EML is the main material (H-3): the imidazole compound 1 provided by the present invention (weight ratio is 97:3) with a thickness of 35 nanometers, and ETL is ET-4:LiQ (weight ratio is 50:50) with a thickness of 35 nanometers, and then cathode Al is evaporated to be 70 nanometers to prepare an organic electroluminescent diode, which is recorded as Application Example 1.

[0125] Referring to the method provided in Application Example 1, the luminescent materials listed in Table 1 were selected as the implementation objects to replace compound 1, and they were co-evaporated with the main material compound H-3 in a weight ratio of 3:97 to form a luminescent layer to prepare an organic electroluminescent diode, which is recorded as Application Example 2 to Application Example 32.

[0126] Preparation of Comparative Example 1

[0127] Comparative Example 1 was prepared by referring to the method provided in Application Example 1, except that BN-1 was used as the guest material of the light-emitting layer in Comparative Example 1 to replace the imidazole boron nitrogen compound of the present invention. The chemical structure of the compound BN-1 in Comparative Example 1 is as follows:

[0128]

[0129] The current efficiency, voltage, life and other characteristics of the device embodiments and comparative examples prepared above were tested by standard methods, and the device luminescence characteristic data are shown in Table 1.

[0130] As can be seen from Table 1, compared with Comparative Example 1, although Application Examples 1 to 32 do not have obvious differences in FWHM, they all show more prominent advantages in current efficiency and lifespan, reflecting their good device performance. The improvement of the performance of each device in the application examples of the present invention is based on the boron nitrogen compound with a specific substitution structure, especially the addition of the imidazole group, which makes the compound material have better carrier transport ability, and the compound of the present invention is used as the guest material of the light-emitting layer to prepare an electronic device, so that the device has higher current efficiency and lifespan. It shows that the imidazole-containing compound provided by the present invention has certain commercial application value.

[0131] The above description is only a preferred specific implementation manner of the present invention, but the protection scope of the present invention is not limited thereto. Any technician familiar with the technical field can make equivalent replacements or changes according to the technical scheme and inventive concept of the present invention within the technical scope disclosed by the present invention, which should be covered by the protection scope of the present invention.

Claims

1. A boron-nitrogen compound, characterized in that: The boron-nitrogen compound is selected from any one of the chemical structures shown below, wherein "D" represents deuterium:

2. Use of the boron nitrogen compound according to claim 1 in the preparation of electronic devices, characterized in that: The boron nitrogen compound is used as a guest material of a light-emitting layer in an organic electroluminescent device.

3. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises a cathode, an anode and at least one organic functional layer therebetween; the organic functional layer comprises the boron nitrogen compound according to claim 1, and the boron nitrogen compound is contained in the organic functional layer as a guest material of the light-emitting layer.

4. An organic optoelectronic device, characterized in that: The organic photoelectric device includes: a substrate layer; a first electrode; a second electrode facing the first electrode; and a light-emitting material layer arranged between the first electrode and the second electrode; wherein the light-emitting material layer contains the boron nitrogen compound according to claim 1, and the boron nitrogen compound is contained in the light-emitting material layer as a guest material.

5. A composition, characterized in that The composition comprises the boron nitrogen compound as claimed in claim 1.

6. A preparation, characterized in that The preparation comprises the boron nitrogen compound according to claim 1 and at least one solvent.

7. A display or lighting device, characterized in that: The device comprises one or more of the organic electroluminescent devices according to claim 3.

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