Boron nitrogen compound and organic electroluminescent device and application thereof

Abstract

The present invention relates to the technical field of organic photoelectric material preparation, and specifically to a boron nitrogen compound and an organic electroluminescent device and application. The boron nitrogen compound provided by the present invention has good carrier transport capability, good energy transfer performance between the host and the guest, exciton utilization efficiency, and thermal stability; introducing multiple large steric hindrance groups around the luminescent group helps to weaken the interaction between the luminescent molecules and can reduce the concentration quenching effect; using it as a functional layer, especially as a luminescent layer in an organic electroluminescent device, achieves higher current efficiency and device life.

Description

Technical Field

[0001] The invention relates to the technical field of organic photoelectric material preparation, and in particular to a boron nitrogen compound and an organic electroluminescent device and application thereof. 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 mechanism of OLED luminescence 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 materials. Summary of the invention

[0003] The purpose of the present invention is to provide a boron nitrogen compound, an organic electroluminescent device and its application in view of the deficiencies of the prior art. The boron nitrogen compound provided by the present invention has good thermal stability, and its carrier transport capacity is improved by introducing an electron-donating N-containing group, and the introduction of multiple large steric hindrance groups around the luminescent group can reduce the interaction force between the luminescent molecules, and the energy transfer performance between the host and the guest can be effectively improved 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 having a structure represented by the following formula (I):

[0006] ;

[0007] In formula (I), Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C30 aromatic amine groups, substituted or unsubstituted C6-C30 nitrogen heteroaryl groups; R1-R4 are independently selected from hydrogen, deuterium, C1-C24 alkyl groups, substituted or unsubstituted C3-C24 cycloalkyl groups, substituted or unsubstituted C6-C30 aromatic groups, substituted or unsubstituted C6-C30 heteroaryl groups; when containing heteroatoms, the heteroatoms in the heteroaryl groups are selected from O and S; when containing substituents, the substituents are selected from any one or more of deuterium and C1-C24 alkyl groups.

[0008] Preferably, R1-R4 are each independently selected from one or more of hydrogen, deuterium, methyl, ethyl, propyl, tert-butyl, phenyl, biphenyl, tert-butylphenyl, dimethylfluorenyl, dibenzofuranyl, dibenzothienyl, and methyl-substituted tetrahydronaphthyl.

[0009] More preferably, R2 and R3 are identically or differently selected from one of hydrogen, deuterium, methyl, ethyl, propyl and tert-butyl.

[0010] Preferably, Ar1 and Ar2 are each independently selected from one of the following structures:

[0011] ;

[0012] Wherein, R5-R9 may be unsubstituted, singly substituted or polysubstituted; in the case of being substituted by multiple substituents, the multiple substituents may be the same or different from each other; R5-R 10 Each of them is identically or differently selected from one or more of hydrogen, deuterium, C1-C24 alkyl, substituted or unsubstituted C3-C24 cycloalkyl, substituted or unsubstituted C6-C30 aryl. When it contains a substituent, the substituent is selected from deuterium and C1-C24 alkyl.

[0013] More preferably, the R5-R 10 Each of them is identically or differently selected from one or more of hydrogen, deuterium, methyl, ethyl, propyl, tert-butyl, pentyl, hexyl, heptyl, phenyl, and cyclopentyl.

[0014] Preferably, at least one hydrogen in the compound represented by formula (I) of the present invention may be substituted by deuterium, tritium, cyano or halogen.

[0015] According to one or more embodiments, the boron nitrogen compound provided by the present invention is selected from any one of the chemical structures shown below, wherein "D" represents deuterium:

[0016] .

[0017] 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.

[0018] 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 photoelectric devices, organic optical detectors, organic photoreceptors, organic field quenching devices (O-FQDs), light emitting electrochemical cells (LECs), and organic laser diodes (O-lasers).

[0019] According to one or more embodiments, the present invention further provides an organic electroluminescent device, comprising a cathode, an anode and an organic functional layer therebetween; the organic functional layer comprises a boron nitrogen compound having a general structure as shown in formula (I) above.

[0020] In a preferred embodiment, 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 the above formula (I); wherein the mass percentage of the boron-nitrogen compound is 0.1%-50%.

[0021] 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.

[0022] The present invention also provides a composition, which comprises a boron-nitrogen compound having a general structure as shown in the above formula (I).

[0023] 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, for example, unsaturated hydrocarbon solvents, halogenated saturated hydrocarbon solvents, halogenated unsaturated hydrocarbon solvents, ether solvents or ester solvents well known to those skilled in the art; 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.

[0024] The present invention also provides a display or lighting device, which comprises one or more of the organic electroluminescent device or the photoelectric device as described above.

[0025] Compared with the prior art, the beneficial effects of the present invention are as follows: the boron nitrogen compounds involved in the present invention have good thermal stability and narrow half-peak width; in particular, multiple electron-donating groups such as aromatic amine groups and carbazole groups are introduced around the luminescent groups in the compounds at the same time, so that the compounds exhibit good carrier transport capabilities. In addition, the compounds of the present invention can also effectively improve the energy transfer performance and exciton utilization efficiency between the subject and the guest, and the nitrogen-containing large steric hindrance group can effectively reduce the interaction between the luminescent molecules. Specifically, the boron nitrogen compounds of the present invention are used as functional layers, especially as luminescent 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 of the 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

[0026] 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.

[0027] For the purposes of the present invention, the present invention is not intended to be limited in any way by the substituents allowed by organic compounds. Likewise, the term "substituted" or "substituted" includes implicit conditions that such substitutions conform to the valence bonds allowed by the substituted atom and the substituent, and that the substitution results in a stable compound (e.g., a compound that does not spontaneously undergo transformation (e.g., by rearrangement, cyclization, elimination, etc.). It is also contemplated that, in certain aspects, unless explicitly indicated to the contrary, a single substituent can further optionally be substituted (i.e., further substituted or unsubstituted).

[0028] The "substituted..." in the present invention, such as substituted C3-C24 cycloalkyl, substituted C6-C30 aryl, substituted C6-C30 heteroaryl, etc., refers to being monosubstituted or polysubstituted by groups independently selected from, but not limited to, deuterated groups, C1-C14 alkyl groups, C3-C12 cycloalkyl groups, C6-C30 aryl groups, etc., preferably selected from, deuterated groups, methyl groups, ethyl groups, isopropyl groups, tert-butyl groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, anthracenyl groups, phenanthrenyl groups, triphenylene groups, etc. , peryl, pyrenyl, benzyl, tolyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, diphenylamino, dimethylamino, carbazolyl, 9-phenylcarbazolyl, acridinyl, furanyl, thienyl, benzofuranyl, benzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothienyl, phenothiazinyl, phenoxazinyl, indolyl, mono- or poly-substituted. In addition, the above substituents may be substituted by one or more substituents described by deuterium, halogen atoms, cyano, alkyl, cycloalkyl, silyl, aryl. The substitution may be by single bond substitution or condensed substitution.

[0029] 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.

[0030] 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.

[0031] 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, it has 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.

[0032] The "heteroaryl" of the present invention refers to a general term for a group obtained by replacing one or more aromatic carbon atoms in an aromatic group with a heteroatom, wherein the heteroatom includes but is not limited to oxygen, sulfur or nitrogen atoms, and the heteroaryl group may be a monocyclic heteroaryl group or a condensed ring heteroaryl group, and examples may include pyridyl, pyrrolyl, pyridyl, thienyl, furyl, indolyl, quinolyl, isoquinolyl, benzothienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, etc., but are not limited thereto. The singular forms "a", "an" and "the" used in the specification and the appended claims include plural references, otherwise the context will clearly indicate otherwise. Therefore, for example, a reference to a "component" includes a mixture of two or more components.

[0033] Unless otherwise stated, all commercial reagents involved in the following experiments were used directly after purchase.

[0034] 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):

[0035]

[0036] 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:

[0037] 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:

[0038]

[0039] In a preferred embodiment of the present invention, the OLED device of the present invention contains a host material, and the host material 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:

[0040]

[0041] The preparation method of the boron nitrogen compound of the present invention and the luminescent properties of the device are explained in detail in conjunction with the following examples.

[0042] Example 1: Synthesis of Compound 1

[0043]

[0044] (1) Synthesis of compound 1-3: Compound 1-1 (315 mg, 1 mmoL) and compound 1-2 (149 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 heated under 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 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 = 1:3 to obtain product 1-3 (187 mg, yield 49%). Mass spectrum m / z, theoretical value 383.17; measured value M+H: 384.19;

[0045] (2) Synthesis of compound 1-6: Compound 1-4 (301 mg, 1 mmoL) and compound 1-5 (282 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 heated under reflux for 24 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 1-6 (312 mg, yield 69%). Mass spectrum m / z, theoretical value 455.13; measured value M+H: 456.15;

[0046] (3) Synthesis of compound 1-7: Compound 1-6 (456 mg, 1 mmoL) and compound 1-2 (149 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 heated under 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 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 = 1:3 to obtain product 1-7 (285 mg, yield 54%). Mass spectrum m / z, theoretical value 524.32; measured value M+H: 525.35;

[0047] (4) Synthesis of compound 1-10: Compound 1-8 (279 mg, 1 mmoL) and compound 1-9 (288 mg, 1 mmoL) were dissolved in 50 mL DMF solution, and potassium carbonate (691 mg, 5 mmoL) was added. The reaction system was heated at 140 degrees Celsius for 24 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 1-10 (327 mg, yield 60%). Mass spectrum m / z, theoretical value 545.01; measured value M+H: 546.03;

[0048] (5) Synthesis of compound 1-11: Compound 1-10 (547 mg, 1 mmoL) and compound 1-7 (524 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 heated under 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 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 (305 mg, yield 31%). Mass spectrum m / z, theoretical value 989.41; measured value M+H: 990.43;

[0049] (6) Synthesis of compound 1-12: Compound 1-11 (991 mg, 1 mmoL) and compound 1-3 (383 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 heated under 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 with sodium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting crude product was separated and purified by silica gel chromatography with the eluent being dichloromethane: petroleum ether = 1:4 to obtain product 1-12 (423 mg, yield 33%). Mass spectrum m / z, theoretical value 1292.65; measured value M+H: 1293.68;

[0050] (7) Synthesis of compound 1: Under nitrogen atmosphere and zero temperature, tert-butyl lithium (1.88 mL, 1.6 M pentane solution, 3 mmoL) was slowly added dropwise to a solution of compound 1-12 (1294 mg, 1 mmoL) in tert-butylbenzene (100 mL). The system was reacted at 60 °C for 4 hours, then cooled to -50 °C, and then BBr3 (494 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 distillation under reduced pressure, and the crude product was separated and purified by silica gel chromatography, with the eluent being dichloromethane:petroleum ether=1:6, to obtain product 1 (275 mg, yield 22%). Mass spectrum m / z, theoretical value 1266.67; measured value M+H: 1267.69.

[0051] Example 2: Synthesis of Compound 3

[0052] Compound 3 was synthesized by referring to the synthetic route of compound 1. The yield of the final product was 26%. Mass spectrum m / z, theoretical value 1322.74; measured value M+H: 1323.76.

[0053] Example 3: Synthesis of Compound 5

[0054] Compound 5 was synthesized by referring to the synthetic route of compound 1. The yield of the final product was 25%. Mass spectrum m / z, theoretical value 1326.67; measured value M+H: 1327.69.

[0055] Example 4: Synthesis of Compound 6

[0056] Compound 6 was synthesized by referring to the synthetic route of compound 1. The yield of the final product was 24%. Mass spectrum m / z, theoretical value 1326.67; measured value M+H: 1327.69.

[0057] Example 5: Synthesis of Compound 8

[0058] Compound 8 was synthesized by referring to the synthetic route of compound 1. The yield of the final product was 31%. Mass spectrum m / z, theoretical value 1286.64; measured value M+H: 1287.67.

[0059] Example 6: Synthesis of Compound 11

[0060] Compound 11 was synthesized by referring to the synthetic route of compound 1. The yield of the final product was 25%. Mass spectrum m / z, theoretical value 1326.67; measured value M+H: 1327.69.

[0061] Example 7: Synthesis of Compound 15

[0062] Referring to the synthetic route of compound 1, compound 15 was synthesized. The yield of the final product was 28%. Mass spectrum m / z, theoretical value 1291.68; measured value M+H: 1292.71.

[0063] Example 8: Synthesis of Compound 16

[0064] Referring to the synthetic route of compound 1, compound 16 was synthesized. The yield of the final product was 24%. Mass spectrum m / z, theoretical value 1300.62; measured value M+H: 1301.65.

[0065] Example 9: Synthesis of Compound 18

[0066] Referring to the synthetic route of compound 1, compound 18 was synthesized. The yield of the final product was 26%. Mass spectrum m / z, theoretical value 1300.62; measured value M+H: 1301.64.

[0067] Example 10: Synthesis of Compound 19

[0068] Referring to the synthetic route of compound 1, compound 19 was synthesized. The yield of the final product was 22%. Mass spectrum m / z, theoretical value 1300.62; measured value M+H: 1301.64.

[0069] Example 11: Synthesis of Compound 21

[0070] Compound 21 was synthesized by referring to the synthetic route of compound 1. The yield of the final product was 26%. Mass spectrum m / z, theoretical value 1300.62; measured value M+H: 1301.65.

[0071] Example 12: Synthesis of Compound 22

[0072] Compound 22 was synthesized by referring to the synthetic route of compound 1. The yield of the final product was 25%. Mass spectrum m / z, theoretical value 1288.66; measured value M+H: 1289.68.

[0073] Example 13: Synthesis of Compound 25

[0074] Referring to the synthetic route of compound 1, compound 25 was synthesized. The yield of the final product was 27%. Mass spectrum m / z, theoretical value 1328.69; measured value M+H: 1329.71.

[0075] Example 14: Synthesis of Compound 30

[0076] Compound 30 was synthesized by referring to the synthetic route of compound 1. The yield of the final product was 32%. Mass spectrum m / z, theoretical value 1344.72; measured value M+H: 1345.74.

[0077] Example 15: Synthesis of Compound 36

[0078] Compound 36 was synthesized by referring to the synthetic route of compound 1. The yield of the final product was 25%. Mass spectrum m / z, theoretical value 1293.69; measured value M+H: 1294.72.

[0079] Example 16: Synthesis of Compound 39

[0080] Compound 39 was synthesized by referring to the synthetic route of compound 1. The yield of the final product was 31%. Mass spectrum m / z, theoretical value 1302.64; measured value M+H: 1303.66.

[0081] Example 17: Synthesis of Compound 40

[0082] Compound 40 was synthesized by referring to the synthetic route of compound 1. The yield of the final product was 28%. Mass spectrum m / z, theoretical value 1302.64; measured value M+H: 1303.67.

[0083] Example 18: Synthesis of Compound 44

[0084] Compound 44 was synthesized by referring to the synthetic route of compound 1. The yield of the final product was 29%. Mass spectrum m / z, theoretical value 1374.77; measured value M+H: 1375.79.

[0085] Example 19: Synthesis of Compound 46

[0086] Referring to the synthetic route of compound 1, compound 46 was synthesized. The yield of the final product was 23%. Mass spectrum m / z, theoretical value 1246.71; measured value M+H: 1247.73.

[0087] Example 20: Synthesis of Compound 56

[0088] Referring to the synthetic route of compound 1, compound 56 was synthesized. The yield of the final product was 28%. Mass spectrum m / z, theoretical value 1306.71; measured value M+H: 1307.73.

[0089] Example 21: Synthesis of Compound 61

[0090] Compound 61 was synthesized by referring to the synthetic route of compound 1. The yield of the final product was 24%. Mass spectrum m / z, theoretical value 1280.65; measured value M+H: 1281.67.

[0091] Example 22: Synthesis of Compound 66

[0092] Referring to the synthetic route of compound 1, compound 66 was synthesized. The yield of the final product was 26%. Mass spectrum m / z, theoretical value 1334.70; measured value M+H: 1335.72.

[0093] Example 23: Synthesis of Compound 69

[0094] Referring to the synthetic route of compound 1, compound 69 was synthesized. The yield of the final product was 30%. Mass spectrum m / z, theoretical value 1304.78; measured value M+H: 1305.81.

[0095] Example 24: Synthesis of Compound 73

[0096] Compound 73 was synthesized by referring to the synthetic route of compound 1. The yield of the final product was 29%. Mass spectrum m / z, theoretical value 1268.69; measured value M+H: 1269.72.

[0097] Example 25: Synthesis of Compound 81

[0098] Compound 81 was synthesized by referring to the synthetic route of compound 1. The yield of the final product was 27%. Mass spectrum m / z, theoretical value 1273.72; measured value M+H: 1274.75.

[0099] Example 26: Synthesis of Compound 85

[0100] Compound 85 was synthesized by referring to the synthetic route of compound 1. The yield of the final product was 26%. Mass spectrum m / z, theoretical value 1282.67; measured value M+H: 1283.69.

[0101] Example 27: Synthesis of Compound 91

[0102] Compound 91 was synthesized by referring to the synthetic route of compound 1. The yield of the final product was 23%. Mass spectrum m / z, theoretical value 1312.66; measured value M+H: 1313.68.

[0103] Example 28: Synthesis of Compound 95

[0104] Compound 95 was synthesized by referring to the synthetic route of compound 1. The yield of the final product was 27%. Mass spectrum m / z, theoretical value: 1291.67; measured value: M+H: 1292.69.

[0105] Example 29: Synthesis of Compound 96

[0106] Compound 96 was synthesized by referring to the synthetic route of compound 1. The yield of the final product was 24%. Mass spectrum m / z, theoretical value 1234.61; measured value M+H: 1235.63.

[0107] Example 30: Synthesis of Compound 99

[0108] Compound 99 was synthesized by referring to the synthetic route of compound 1. The yield of the final product was 24%. Mass spectrum m / z, theoretical value 1217.65; measured value M+H: 1218.67.

[0109] Example 31: Synthesis of Compound 104

[0110] Compound 104 was synthesized by referring to the synthetic route of compound 1. The yield of the final product was 27%. Mass spectrum m / z, theoretical value: 1266.67; measured value: M+H: 1267.69.

[0111] Example 32: Synthesis of Compound 105

[0112] Compound 105 was synthesized by referring to the synthetic route of compound 1. The yield of the final product was 23%. Mass spectrum m / z, theoretical value: 1192.65; measured value: M+H: 1193.67.

[0113] Example 33: Synthesis of Compound 109

[0114] Referring to the synthetic route of compound 1, compound 109 was synthesized. The yield of the final product was 23%. Mass spectrum m / z, theoretical value 1264.66; measured value M+H: 1265.68.

[0115] Example 34: Synthesis of Compound 111

[0116] Compound 111 was synthesized by referring to the synthetic route of compound 1. The yield of the final product was 27%. Mass spectrum m / z, theoretical value: 1348.75; measured value: M+H: 1349.77.

[0117] Example 35: Synthesis of Compound 119

[0118] Referring to the synthetic route of compound 1, compound 119 was synthesized. The yield of the final product was 29%. Mass spectrum m / z, theoretical value 1294.62; measured value M+H: 1295.64.

[0119] Example 36: Synthesis of Compound 126

[0120] Referring to the synthetic route of compound 1, compound 126 was synthesized. The yield of the final product was 28%. Mass spectrum m / z, theoretical value 1302.77; measured value M+H: 1303.79.

[0121] Example 37: Synthesis of Compound 132

[0122] Compound 132 was synthesized by referring to the synthetic route of compound 1. The yield of the final product was 26%. Mass spectrum m / z, theoretical value 1322.74; measured value M+H: 1323.76.

[0123] Example 38: Synthesis of Compound 136

[0124] Referring to the synthetic route of compound 1, compound 136 was synthesized. The yield of the final product was 27%. Mass spectrum m / z, theoretical value 1286.64; measured value M+H: 1287.67.

[0125] Example 39: Synthesis of Compound 142

[0126] Compound 142 was synthesized by referring to the synthetic route of compound 1. The yield of the final product was 31%. Mass spectrum m / z, theoretical value: 1300.62; measured value: M+H: 1301.64.

[0127] Fabrication of OLED devices:

[0128] 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 a boron nitrogen 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.

[0129] 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-15:P-3 (weight ratio is 95:5) with a thickness of 10 nanometers; HTL is HT-5 with a thickness of 90 nanometers; EBL is HT-7 with a thickness of 10 nanometers, EML is the main material (H-5): compound 1 (weight ratio is 97:3) with a thickness of 35 nanometers, 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.

[0130] Referring to the method provided in Application Example 1, the boron nitrogen compounds in Table 1 were selected as implementation objects to replace Compound 1 in Application Example 1 to prepare organic electroluminescent diodes, which are recorded as Application Examples 2 to Application Example 30, and Comparative Examples 1 and 2.

[0131] The chemical structures of Ref-1 and Ref-2 in the comparative example are as follows:

[0132]

[0133] 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.

[0134] Table 1. Device luminescence characteristics data table

[0135]

[0136] As can be seen from Table 1, compared with Comparative Examples 1 and 2, the compounds provided by the present invention show more prominent advantages in current efficiency and lifespan, reflecting its good device performance. The performance improvement of each device of the present invention in the application example is based on the boron nitrogen compound with a specific substitution structure, especially the introduction of electron-donating groups around the luminescent group so that the compound has better carrier transport ability, and the introduction of multiple large steric groups can reduce the interaction between the luminescent molecules. The compounds of the present invention are used as the guest material of the luminescent layer to prepare electronic devices, so that the devices have higher current efficiency and lifespan. It shows that the boron nitrogen compound provided by the present invention has certain commercial application value.

[0137] 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 has a structure shown in formula (I), In formula (I), R1 and R4 are each independently selected from one or more of phenyl, biphenyl, tert-butylphenyl, dimethylfluorenyl, dibenzofuranyl, dibenzothienyl, and methyl-substituted tetrahydronaphthyl, which may be substituted by deuterium or tert-butyl; R2 and R3 are each independently selected from hydrogen or tert-butyl; Ar1 ​​and Ar2 are each independently selected from the following structures: R5-R9 are unsubstituted, singly substituted or polysubstituted; in the case of being substituted by multiple substituents, the multiple substituents are the same or different from each other; 10 Each is identically or differently selected from one or more of hydrogen, deuterium, methyl, tert-butyl, pentyl and phenyl.

2. The boron nitrogen compound according to claim 1, characterized in that At least one hydrogen in formula (I) may be substituted by deuterium.

3. 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:

4. Use of the boron nitrogen compound according to any one of claims 1 to 3 as a guest material for a light-emitting layer in the preparation of electronic devices.

5. The use according to claim 4, characterized in that: The electronic devices are organic electroluminescent devices, organic integrated circuits, organic field effect transistors, organic thin film transistors, organic light emitting transistors, organic solar cells, organic photoelectric devices, organic optical detectors, organic photoreceptors, organic field quenching devices, light emitting electrochemical cells and organic laser diodes.

6. 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 a light-emitting layer, and the light-emitting layer comprises the boron nitrogen compound according to any one of claims 1 to 3.

7. An organic optoelectronic device, characterized in that: The organic photoelectric device comprises: 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; the light-emitting material layer comprises the boron nitrogen compound according to any one of claims 1 to 3.

8. A composition, characterized in that The composition comprises the boron nitrogen compound according to any one of claims 1 to 3.

9. A preparation, characterized in that The preparation comprises the boron nitrogen compound according to any one of claims 1 to 3 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 according to claim 6 or the organic photoelectric device according to claim 7.

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