Boron-nitrogen compound, OLED and organic light-emitting device having the compound

Abstract

The present invention relates to the technical field of organic optoelectronic material preparation, and in particular to a boron nitrogen compound, an OLED, and an organic light-emitting device comprising the compound. The boron nitrogen compound of the present invention, by combining a parent core with a tetralin limiting group substituted with a bis-tert-butylphenyl group or a methyl group, can enhance the thermal stability of the compound and exhibit excellent luminescence properties. The boron nitrogen compound provided by the present invention, when used as a light-emitting layer material, can effectively lower the driving voltage of an organic light-emitting device while maintaining voltage stability and improving luminous efficiency.

Description

Technical Field

[0001] The present invention relates to the technical field of organic photoelectric material preparation, and in particular to a boron nitrogen compound, an OLED having the compound, and an organic light-emitting device. Background Art

[0002] With the development of multimedia technology and the increasing demand for information technology, the performance requirements for panel displays are becoming increasingly higher. Organic light-emitting diodes (OLEDs), also known as organic electroluminescent devices, are a technology that converts electrical energy into light energy through organic light-emitting materials by applying voltage to the organic electroluminescent element, injecting holes from the anode and electrons from the cathode into the light-emitting layer. The injected holes and electrons recombine to form excitons, which then emit light.

[0003] The light-emitting layer in OLED devices mostly uses a host-guest luminescence system, that is, a guest material is doped into the host material. In the field of OLED materials, scholars and technology developers from all walks of life are actively researching organic materials that have the characteristics of emitting blue, one of the three primary colors of light, and organic materials that have the ability to transport holes, electrons, and other charges (possibly becoming semiconductors or superconductors). Currently, the research focus on blue-light doping materials is mainly on boron-nitrogen fused-ring molecules, but the variety and quantity of existing materials are still relatively small, making the study of structure-activity relationships more difficult. In addition, in application, display technology still suffers from high driving voltage and short display life, which seriously hinders the further application of this technology.

[0004] Therefore, continuous efforts are needed to develop organic light-emitting devices with low voltage drive, high brightness and long life. Finding suitable OLED optoelectronic functional materials for OLED devices to solve the above problems is a long-term need in this field. Summary of the Invention

[0005] To address the above technical problems, the present invention provides a boron-nitrogen compound, an OLED, and a display or lighting device comprising the compound. By combining a parent core with a tetralin-substituted bis-tert-butylphenyl group and a methyl group as limiting groups, the boron-nitrogen compound improves luminous efficiency and thermal stability, and its molecular structure is easily modified. As a light-emitting layer material, the boron-nitrogen compound provided by the present invention can effectively lower the driving voltage of an organic light-emitting device while maintaining voltage stability and improving luminous efficiency.

[0006] The boron-nitrogen compound provided by the present invention is realized by the following technical solution:

[0007] A boron-nitrogen compound having a structure shown in the following formula (I):

[0008] ;

[0009] In formula (I), X is selected from O, S, and Se atoms; R is selected from deuterated or undeuterated C1-C20 alkyl, substituted or unsubstituted phenyl, and substituted or unsubstituted tetrahydronaphthyl; when containing substituents, the substituents are selected from hydrogen, deuterium, and C1-C20 alkyl;

[0010] R1-R2 are each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C36 heteroaryl. When R1-R2 contain substituents, the substituents are selected from any one or more combinations of C1-C20 alkyl, C3-C20 cycloalkyl, and C6-C30 aryl; and at least one of R1-R2 is selected from or , wherein Ra-R1 are each independently selected from hydrogen, deuterium, C1-C20 alkyl, C3-C20 cycloalkyl, C6-C30 aryl, and R1-R2 can be connected to the N atom through any site in Ra-R1;

[0011] R3 and R4 are each independently selected from hydrogen, C1-C20 alkyl, and C3-C20 cycloalkyl; R3 and R4 represent a polysubstituted group, which may be unsubstituted, monosubstituted, or polysubstituted. In the case of polysubstituted groups, the multiple substituents may be the same or different from each other, and the multiple substituents may be interconnected and fused to form a ring.

[0012] Preferably, R1-R2 are each independently selected from substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted tert-butylphenyl, substituted or unsubstituted benzotetramethylcyclohexyl.

[0013] More preferably, the R1-R2 are each independently selected from any one of the following structures: ; The Ra-Rl are each independently selected from one or more combinations of hydrogen, deuterium, tert-butyl, phenyl, and di-tert-butylphenyl.

[0014] More preferably, when one of R1-R2 is selected from When the other is selected from any one of the following structures, wherein "#" represents a connection site, Ph represents a phenyl group, and tBu represents a tert-butyl group:

[0015] .

[0016] Preferably, R3 and R4 are each independently selected from a fused tetramethylcyclohexyl group, a tert-butyl group or a phenyl group; more preferably, at least one of R3 and R4 is selected from a fused tetramethylcyclohexyl group.

[0017] Preferably, R is independently selected from deuterated or undeuterated tert-butyl, methyl-substituted tetrahydronaphthyl, substituted or unsubstituted phenyl. When substituted, the substituent is hydrogen, deuterium, or methyl.

[0018] According to one or more embodiments, the present invention provides a boron nitrogen compound, wherein the compound is selected from any one of the chemical structures shown below, wherein Ph represents a phenyl group and tBu represents a tert-butyl group:

[0019] .

[0020] The present invention also provides a use of the boron nitrogen compound described above in an organic electroluminescent device.

[0021] The present invention also provides an organic electroluminescent device, comprising:

[0022] substrate layer;

[0023] a first electrode, the first electrode being on the substrate;

[0024] an organic light-emitting functional layer, the organic light-emitting functional layer being on the first electrode;

[0025] a second electrode, the second electrode being on the organic light-emitting functional layer;

[0026] The organic light-emitting functional layer comprises the boron-nitrogen compound described above. Preferably, the organic light-emitting functional layer comprises a light-emitting layer; the light-emitting layer comprises the boron-nitrogen compound described above.

[0027] The present invention also provides a composition comprising the boron nitrogen compound of formula (I).

[0028] The present invention also provides a preparation comprising a boron nitrogen compound having a structure represented by formula (I) above or a composition as described above and at least one solvent. The solvent is not particularly limited and may be any solvent known to those skilled in the art, such as unsaturated hydrocarbon solvents such as toluene, xylene, mesitylene, tetralin, decalin, bicyclohexane, n-butylbenzene, sec-butylbenzene, and tert-butylbenzene; halogenated saturated hydrocarbon solvents such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, hexyl chloride, bromohexane, chlorocyclohexane, and bromocyclohexane; halogenated unsaturated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, and trichlorobenzene; ether solvents such as tetrahydrofuran and tetrahydropyran; and ester solvents such as alkyl benzoates.

[0029] The organic electroluminescent device of the present invention can be used in OLED lighting or display devices. Preferably, the organic electroluminescent device prepared by the present invention is used in smartphones, tablet computers, smart wearable devices, televisions, VR, micro-displays, and automobile central control screens or automobile taillights.

[0030] The present invention also provides a display or lighting device, which comprises one or more of the organic electroluminescent devices described above.

[0031] In summary, compared with the prior art, the present invention has the following beneficial effects:

[0032] The boron nitrogen compound of the present invention has good stability and film-forming properties by combining the bis-tert-butylphenyl group and the methyl-substituted tetralin limiting group with the parent core. When the boron nitrogen compound provided by the present invention is prepared into an organic light-emitting device, the organic light-emitting device can effectively have a lower driving voltage while maintaining voltage stability, and the luminous efficiency is improved, and the service life of the device can also be improved. DETAILED DESCRIPTION

[0033] The following is a clear and complete description of the technical solutions of the embodiments of the present invention. Obviously, the embodiments described are only some embodiments of the present invention, not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without making any creative efforts shall fall within the scope of protection of the present invention.

[0034] The term "alkyl" refers to and includes straight-chain and branched alkyl groups. Preferred alkyl groups are those containing 1 to 20 carbon atoms and include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, and the like. In addition, the alkyl group may be optionally substituted.

[0035] The term "cycloalkyl" refers to and includes monocyclic, polycyclic and spiroalkyl groups. Preferred cycloalkyl groups are those containing 3 to 20 ring carbon atoms, more preferred cycloalkyl groups are those containing 3 to 12 ring carbon atoms, and particularly preferred are those containing 3 to 6 ring carbon atoms, and include cyclopropyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl, and the like. In addition, the cycloalkyl group may be optionally substituted.

[0036] The term "aryl" refers to and includes monocyclic aromatic hydrocarbon groups and polycyclic aromatic ring systems. Polycyclic rings can have two or more rings in which two carbon atoms are shared by two adjacent rings (the rings are "fused"), wherein at least one of the rings is an aromatic hydrocarbon group, for example, the other rings can be cycloalkyl, cycloalkenyl, aryl, heterocycle and / or heteroaryl. Preferred aryl groups are aryl groups containing six to thirty carbon atoms, more preferably six to twelve carbon atoms. Especially preferred are aryl groups with six carbon atoms, ten carbon atoms or twelve carbon atoms. Suitable aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthren, phenanthrene, fluorene, pyrene, perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. In addition, aryl groups can be optionally substituted.

[0037] The term "heteroaryl" refers to a general term for groups in which one or more aromatic carbon atoms in an aromatic group are replaced by heteroatoms, including but not limited to oxygen, sulfur, silicon, or nitrogen atoms. The heteroaryl group may be a monocyclic heteroaryl group or a condensed ring heteroaryl group, and may be a heteroaryl group having 5 to 36 carbon atoms, preferably 6 to 20 carbon atoms. Examples may include, but are not limited to, pyridyl, pyrrolyl, pyridyl, thienyl, furyl, indolyl, quinolyl, isoquinolyl, benzothienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, and the like.

[0038] Throughout this specification, unless explicitly stated to the contrary, references to "comprising" any component will be understood to implicitly include, but not exclude, any other elements. Furthermore, it should be understood that throughout this specification, when an element such as a layer, film, region, or substrate is referred to as being "on" or "over" another element, it can be "directly on" the other element, or intervening elements may be present. Furthermore, "on" or "above" refers to being above the target portion, not necessarily above in terms of gravity.

[0039] An object of the present invention is to provide an organic electroluminescent device, the organic electroluminescent device comprising: a substrate layer; a first electrode, the first electrode being on the substrate; an organic light-emitting functional layer, the organic light-emitting functional layer being on the first electrode; a second electrode, the second electrode being on the organic light-emitting functional layer; the organic light-emitting functional layer comprising a light-emitting layer, the light-emitting layer comprising a or Structure of boron-nitrogen compounds.

[0040] In one embodiment of the present invention, the light-emitting layer in the organic electroluminescent (OLED) device comprises one or more compounds represented by the above general formula (I) as light-emitting doping materials.

[0041] In a preferred embodiment of the present invention, an OLED is provided, comprising a substrate, an anode, a cathode, and an organic light-emitting functional layer. The organic light-emitting functional layer may include a light-emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, etc., or may include only the light-emitting layer and one or more other layers. The light-emitting layer comprises a light-emitting dopant material composed of one or more of the compounds represented by the above-mentioned general formula (I). Optionally, a capping layer, a protective layer, and / or an encapsulation layer are further provided above the organic light-emitting functional layer.

[0042] The substrate of the present invention can be any substrate used in typical organic light-emitting devices. It can be glass or transparent plastic, or an opaque material such as silicon or stainless steel, or a flexible PI film. Different substrates have varying mechanical strength, thermal stability, transparency, surface smoothness, and water resistance, and their applications vary depending on the properties of the substrate.

[0043] As materials for the hole injection layer, the hole transport layer, and the electron injection layer, any material can be selected from known materials used in OLED devices.

[0044] As a host material capable of producing blue fluorescence, green fluorescence and blue-green fluorescence, it not only needs to have extremely high fluorescence quantum luminescence efficiency, but also needs to have an appropriate energy level to effectively cooperate with the guest material to excite and emit light.

[0045] The present invention will be described in detail below with reference to specific examples. Synthesis Examples All raw materials and solvents were purchased commercially unless otherwise specified, and the solvents were used directly without further treatment.

[0046] Example

[0047] Example 1: Synthesis of Compound 001

[0048] Synthesis route:

[0049] ;

[0050] 1) Compound 001-1 (1 mmol) and compound 001-2 (1 mmol) were dissolved in 50 mL of toluene. Under a nitrogen atmosphere, sodium tert-butoxide (2 mmol), palladium acetate (0.05 mmol), and tri-tert-butylphosphine tetrafluoroborate (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 over 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 an eluent ratio of dichloromethane:petroleum ether (1:4) to obtain the intermediate product 001-3.

[0051] 2) Dissolve intermediate 001-3 (1 mmol) and compound 001-4 (1 mmol) in 50 mL of toluene. Under a nitrogen atmosphere, add sodium tert-butoxide (2 mmol), palladium acetate (0.05 mmol), and tri-tert-butylphosphine tetrafluoroborate (0.5 mmol). Reflux the reaction system for 72 hours and then cool to room temperature. Remove the solvent by rotary evaporation, and extract the residue with dichloromethane (3 × 100 mL). Wash the organic phase with water and dry it over sodium sulfate. Remove the solvent by distillation under reduced pressure, and the resulting crude product is separated and purified by silica gel chromatography using a 1:4 ratio of dichloromethane to petroleum ether as the eluent. This gives intermediate 001-5.

[0052] 3) Dissolve intermediate 001-5 (1 mmol) and compound 001-6 (1 mmol) in 50 mL of toluene. Under a nitrogen atmosphere, add sodium tert-butoxide (2 mmol), palladium acetate (0.05 mmol), and tri-tert-butylphosphine tetrafluoroborate (0.5 mmol). Reflux the reaction system for 72 hours and then cool to room temperature. Remove the solvent by rotary evaporation, and extract the residue with dichloromethane (3 × 100 mL). Wash the organic phase with water and dry it over sodium sulfate. Remove the solvent by distillation under reduced pressure, and the resulting crude product is purified by silica gel chromatography using a 1:4 ratio of dichloromethane to petroleum ether as the eluent. This gives intermediate 001-7.

[0053] 4) Dissolve intermediate 001-7 (1 mmol) and compound 001-8 (1 mmol) in 50 mL of toluene. Under a nitrogen atmosphere, add sodium tert-butoxide (2 mmol), palladium acetate (0.05 mmol), and tri-tert-butylphosphine tetrafluoroborate (0.5 mmol). Reflux the reaction system for 72 hours and then cool to room temperature. Remove the solvent by rotary evaporation, and extract the residue with dichloromethane (3 × 100 mL). Wash the organic phase with water and dry it over sodium sulfate. Remove the solvent by distillation under reduced pressure, and purify the resulting crude product by silica gel chromatography with a 1:4 ratio of dichloromethane to petroleum ether to obtain intermediate 001-9.

[0054] 5) Intermediate 001-9 (1 mmol) was dissolved in 60 mL of anhydrous tert-butylbenzene. The reaction system was cooled to -78°C, and BuLi (1 mL, 2 mmol, 2 M in hexane) was slowly added. After reacting at -78°C for 4 hours, BBr (3247 mg, 1 mmol) was slowly added. The reaction was continued at -50°C for 1 hour, then warmed to room temperature. N,N-diisopropylethylamine (387 mg, 3 mmol) was added, and the reaction was heated to 120°C for 12 hours. After cooling to room temperature, 5 mL of 1 M sodium acetate solution 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 resulting crude product was purified by silica gel chromatography using a 1:8 ratio of dichloromethane to petroleum ether as the eluent to obtain the final product 001. The structure of the test target product 001 was obtained by liquid chromatography-mass spectrometry analysis: LC-MS (m / z) (Μ+): the theoretical value was 1054.73, and the test value was 1055.25.

[0055] Example 2: Synthesis of Compound 015

[0056] Compound 015 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 015 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (M+): the theoretical value was 1063.79 and the measured value was 1064.27.

[0057] Example 3: Synthesis of Compound 021

[0058] Compound 021 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 021 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (M+): the theoretical value was 1184.81 and the measured value was 1185.35.

[0059] Example 4: Synthesis of Compound 049

[0060] Compound 049 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 049 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (M+): the theoretical value was 1054.73 and the measured value was 1055.21.

[0061] Example 5: Synthesis of Compound 051

[0062] Compound 051 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 051 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (M+): the theoretical value was 1079.73 and the measured value was 1080.27.

[0063] Example 6: Synthesis of Compound 053

[0064] Compound 053 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 053 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (M+): the theoretical value was 1106.76 and the measured value was 1107.38.

[0065] Example 7: Synthesis of Compound 072

[0066] Compound 072 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 072 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (M+): the theoretical value was 1131.76 and the measured value was 1132.22.

[0067] Example 8: Synthesis of Compound 081

[0068] Compound 081 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 081 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (M+): the theoretical value was 1072.68 and the measured value was 1073.14.

[0069] Example 9: Synthesis of Compound 088

[0070] Compound 088 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. Liquid chromatography-mass spectrometry analysis gave LC-MS (m / z) (M+): theoretical value was 1100.72, and the measured value was 1101.36.

[0071] Example 10: Synthesis of Compound 089

[0072] Compound 089 was synthesized using the same synthesis steps and reaction conditions as in Example 1. Liquid chromatography-mass spectrometry analysis revealed an LC-MS (m / z) value (M+) of 979.61 and a measured value of 980.23.

[0073] Example 11: Synthesis of Compound 090

[0074] Compound 090 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 090 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (M+): the theoretical value was 917.59 and the measured value was 918.07.

[0075] Example 12: Synthesis of Compound 092

[0076] Compound 092 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 092 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (M+): the theoretical value was 1144.78 and the measured value was 1145.26.

[0077] Example 13: Synthesis of Compound 098

[0078] Compound 098 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 098 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (M+): the theoretical value was 1072.68 and the measured value was 1073.22.

[0079] Example 14: Synthesis of Compound 099

[0080] Compound 099 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 099 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (M+): the theoretical value was 1182.79 and the measured value was 1183.27.

[0081] Example 15: Synthesis of Compound 102

[0082] Compound 102 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 102 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (M+): the theoretical value was 1174.68 and the measured value was 1175.24.

[0083] Example 16: Synthesis of Compound 107

[0084] Compound 107 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 107 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (M+): the theoretical value was 1207.79 and the measured value was 1208.31.

[0085] Example 17: Synthesis of Compound 116

[0086] Compound 116 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 116 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (M+): the theoretical value was 1106.63 and the measured value was 1107.11.

[0087] Example 18: Synthesis of Compound 121

[0088] Compound 121 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 121 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (M+): the theoretical value was 1131.63 and the measured value was 1132.21.

[0089] Example 19: Synthesis of Compound 124

[0090] Compound 124 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 124 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (M+): the theoretical value was 1086.66 and the measured value was 1087.12.

[0091] Example 20: Synthesis of Compound 130

[0092] Compound 130 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 130 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (M+): the theoretical value was 999.54 and the measured value was 1000.08.

[0093] Example 21: Synthesis of Compound 140

[0094] Compound 140 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. Liquid chromatography-mass spectrometry analysis gave LC-MS (m / z) (M+): theoretical value was 1125.68, and the measured value was 1126.16.

[0095] Example 22: Synthesis of Compound 148

[0096] Compound 148 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 148 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (M+): the theoretical value was 1056.74 and the measured value was 1057.20.

[0097] Example 23: Synthesis of Compound 159

[0098] Compound 159 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 159 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (M+): the theoretical value was 1209.81 and the measured value was 1210.43.

[0099] Example 24: Synthesis of Compound 162

[0100] Compound 162 was synthesized by referring to the synthesis steps and reaction conditions of Example 1. The compound 162 was analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m / z) (M+): the theoretical value was 1184.81 and the measured value was 1185.47.

[0101] Several examples of the boron nitrogen compounds of the present invention being used in OLED devices are listed below to further illustrate the beneficial effects of the compounds of the present invention. The materials used in the examples were purchased commercially or synthesized independently.

[0102] Fabrication of OLED devices:

[0103] As a reference fabrication method for a device embodiment, the present invention employs a 50-500nm thick ITO / Ag / ITO anode deposited on an alkali-free glass substrate. A hole injection layer (5nm-20nm), a hole transport layer (50-150nm), a luminescence-assisting layer (5-120nm), a light-emitting layer (20-50nm), a hole blocking layer (5-20nm), an electron transport layer (20-80nm), and an electron injection layer (1-10nm) are then deposited on the anode. A semi-transparent cathode is then formed by co-evaporating Mg and Ag (weight ratio 1:9, 100-150nm). The capping compound is then evaporated. Finally, the light-emitting device is encapsulated with an epoxy resin adhesive under a nitrogen atmosphere.

[0104] In a preferred embodiment, the OLED device provided by the present invention has the following structure: an alkali-free glass substrate is first cleaned with isopropyl alcohol using an ultrasonic cleaner for 15 minutes, followed by a 30-minute UV ozone cleaning in air. The treated substrate is then vacuum-deposited with a 100nm thick ITO / Ag / ITO anode. A hole injection layer (HI:PD, 10nm, 2%), a hole transport layer (HT, 130nm), a luminescent auxiliary layer (BP, 5nm), a blue emitting layer (host material: dopant material - BH-1: compound 001 (weight ratio 98:2, 30nm)), a hole blocking layer (HBL, 5nm), an electron transport layer (ET: Lig-1:1, 30nm), and an electron injection layer (Yb, 1nm) are sequentially deposited on the anode. Mg and Ag (weight ratio 1:9, 130nm) are then co-deposited to form a semi-transparent cathode. Compound CPL (65nm) is then deposited as a capping layer. Finally, the light emitting device is encapsulated using epoxy resin adhesive in a nitrogen atmosphere, which is recorded as Application Example 1. The molecular structure formula of the relevant materials is shown below (particularly preferably selected from the following structures, but it does not mean that the present invention is limited to the following structures):

[0105]

[0106] Application Examples 2 to 24 and Comparative Example 1 were prepared according to the method provided in Application Example 1, with the only difference being that the compounds listed in Table 1 were used as doping materials to replace Compound 001 in Application Example 1. The doping materials in Comparative Example 1 are as follows: .

[0107] Performance evaluation of OLED devices:

[0108] The current of the OLED device at different voltages was measured using a Keithley 2365A digital nanovoltmeter, and the current density of the OLED device at different voltages was obtained by dividing the current by the luminous area. The brightness and radiant energy flux density of the OLED device at different voltages were measured using a Konicaminolta CS-2000 spectroradiometer. Based on the current density and brightness of the OLED device at different voltages, the luminance at the same current density (10 mA / cm 2 ) operating voltage Volt and current efficiency (cd / A). BI = E / CIEy, which refers to the Blue Index of blue light and is a parameter that measures the luminous efficiency of blue light. E refers to the current efficiency, and CIEy refers to the vertical coordinate color point obtained by substituting the device's half-width at half-peak wavelength into the CIE1930 software. The test data is shown in Table 1.

[0109] Table 1 Organic electroluminescent devices and their electron luminescence characteristics

[0110]

[0111] As can be seen from Table 1, compared with Comparative Example 1, Application Examples 1 to 24 have lower operating voltages, higher BI luminous efficiencies, and longer service lives. The performance improvements in each application example are based on the introduction of limiting groups such as di-tert-butylphenyl and methyl-substituted tetralin into the boron-nitrogen core structure, resulting in improved luminous efficiency for the boron-nitrogen compound material. Furthermore, the dopant materials in the present invention have excellent compatibility, enabling the blue light-emitting layer to achieve better balance between electron and hole transport and exciton conversion efficiency, reducing device power consumption and increasing service life.

[0112] This specific embodiment is merely an explanation of the present invention and is not intended to limit the present invention. After reading this specification, those skilled in the art may make non-creative modifications to this embodiment as needed. However, as long as such modifications are within the scope of the claims of the present invention, they are protected by patent law.

Claims

1. A boron-nitrogen compound, characterized in that: The compound is selected from any one of the chemical structures shown below, where Ph represents a phenyl group:

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

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

4. Use of the boron nitrogen compound according to claim 1 in the preparation of an organic electroluminescent device.

5. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises: substrate layer; a first electrode, the first electrode being on the substrate; an organic light-emitting functional layer, the organic light-emitting functional layer being on the first electrode; a second electrode, the second electrode being on the organic light-emitting functional layer; The organic light-emitting functional layer includes a boron nitrogen compound, and the boron nitrogen compound is selected from the boron nitrogen compound according to claim 1.

6. Use of the organic electroluminescent device according to claim 5 in preparing a display or lighting device.

7. A display or lighting device, characterized in that: The device comprises the organic electroluminescent device according to claim 5.

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